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WO2013026724A1 - Dihydrofuran derivatives as insecticidal compounds - Google Patents

Dihydrofuran derivatives as insecticidal compounds Download PDF

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Publication number
WO2013026724A1
WO2013026724A1 PCT/EP2012/065753 EP2012065753W WO2013026724A1 WO 2013026724 A1 WO2013026724 A1 WO 2013026724A1 EP 2012065753 W EP2012065753 W EP 2012065753W WO 2013026724 A1 WO2013026724 A1 WO 2013026724A1
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WO
WIPO (PCT)
Prior art keywords
chloro
formula
compound
trifluoromethyl
substituted
Prior art date
Application number
PCT/EP2012/065753
Other languages
French (fr)
Inventor
Julie Clementine Toueg
Tomas Smejkal
Sebastian Volker Wendeborn
Jérôme Yves CASSAYRE
Myriem El Qacemi
Bernhard Breit
Lisa DIAB
Régis Jean Georges MONDIERE
Nicolas Poirier
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Syngenta Participations Ag
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Publication date
Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag
Priority to PCT/EP2012/065753 priority Critical patent/WO2013026724A1/en
Priority to US14/239,373 priority patent/US20140343049A1/en
Publication of WO2013026724A1 publication Critical patent/WO2013026724A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/40—Halogenated unsaturated alcohols
    • C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
    • C07C33/48—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts with unsaturation outside the aromatic rings
    • C07C33/483—Monocyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/20—Oxygen atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/28—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Definitions

  • the present invention relates to certain dihydrofuran derivatives, to processes and intermediates for preparing these derivatives, to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising these derivatives and to methods of using these derivatives to control insect, acarine, nematode and mollusc pests.
  • the invention relates to stereoisomers of said dihydrofuran derivatives.
  • isoxazoline derivatives with insecticidal properties are disclosed, for example, in EP 1,731,512.
  • new biologically active compounds as well as new biologically active compounds displaying superior properties for use as agrochemical active ingredients, for example greater biological activity, different spectrum of activity, increased safety profile, or increased biodegradability.
  • the present invention therefore provides compounds of formula (IA)
  • Q A is Q A 1 or Q A 2
  • P is PI, heterocyclyl or heterocyclyl substituted by one to five Z;
  • a 1 , A 2 , A 3 and A 4 are independently of each other C-H, C-R 5 , or nitrogen;
  • G 1 is oxygen or sulfur
  • R 1 is hydrogen, Ci-Cgalkyl, d-Cgalkoxy-, Ci-Cgalkylcarbonyl-, or Ci-Cgalkoxycarbonyl-;
  • R 2 is Ci-Cgalkyl or Ci-Cgalkyl substituted by one to five R 6 , C 3 -Ciocycloalkyl or C 3 -Ciocycloalkyl substituted by one to five R 7 , aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Ci-C 4 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 , Ci-C 8 alkylaminocarbonyl-Ci-C 4 alkylene, Q- Cghaloalkylaminocarbonyl-Ci-C 4 alkylene, C3-Cgcycloalkyl-aminocarbony
  • R 3 is Ci-Cghaloalkyl
  • R 4 is aryl or aryl substituted by one to five R 9 , or heteroaryl or heteroaryl substituted by one to five R 9 ; each R 5 is independently halogen, cyano, nitro, Ci-Cgalkyl, Ci-Cghaloalkyl, d-Cgalkenyl, d- Cghaloalkenyl, d-Cgalkynyl, Ci-Cghaloalkynyl, C3-Ciocycloalkyl, Ci-Cgalkoxy-, Ci-Cghaloalkoxy-, d- Cgalkylthio-, Ci-Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, or Ci-Cghaloalkylsulfonyl-;
  • each R 6 is independently halogen, cyano, nitro, hydroxy, amino, Ci-Cgalkylamino, (Ci-Cgalkyl) 2 amino, Ci-Cgalkylcarbonylamino, Ci-Cghaloalkylcarbonylamino, Ci-Cgalkoxy-, Ci-Cghaloalkoxy-, aryloxy or aryloxy substituted by one to five R 10 , aryloxy-Ci-C 4 alkylene or aryloxy-Ci-C 4 alkylene wherein the aryl moiety is substituted by one to five R 10 , d-Cgalkylcarbonyl-, Ci-C 8 alkoxycarbonyl-, mercapto, C r Cgalkylthio-, Ci-Cghaloalkylthio-, CpCgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, C r
  • each R 8 is independently halogen, cyano, nitro, oxo, CpCgalkyl, Ci-Cghaloalkyl, CpCgcyanoalkyl, C 2 - Cgalkenyl, C 2 -Cghaloalkenyl, C 2 -Cgalkynyl, C 2 -Cghaloalkynyl, C3-Ciocycloalkyl, d-Ciocycloalkyl-Cr C 4 alkylene, hydroxy, Ci-Cgalkoxy-, Ci-Cghaloalkoxy-, mercapto, CpCgalkylthio-, Ci-Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, Ci-Cghaloalkylsulfonyl-, C r
  • each R 9 is independently halogen, cyano, nitro, CpCgalkyl, Ci-Cghaloalkyl, C 2 -Cgalkenyl, - Cghaloalkenyl, C 2 -Cgalkynyl, C 2 -Cghaloalkynyl, hydroxy, Ci-Cgalkoxy-, Ci-Cghaloalkoxy-, mercapto, d- Cgalkylthio-, Ci-Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, d- Cghaloalkylsulfonyl-, Ci-Cgalkylcarbonyl-, Ci-Cgalkoxycarbonyl-, aryl or aryl substituted by one to five R 10 , or heterocyclyl or heterocyclyl substituted by one to five R 10 ;
  • each R 10 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy-, or d- C 4 haloalkoxy-;
  • each Z is independently halogen, substituted by one to five R 6 , nitro, Cp Ci 2 alkoxy or substituted by one to five R 6 , cyano, Ci-Cgalkylsulfonyl, Ci-Cghaloalkylsulfinyl, hydroxyl or thiol; or a salt or N-oxide thereof.
  • the invention also provides mixtures comprising a compound of formula (IA) and a compound of formula (IB)
  • a 1 , A 2 , A 3 , A 4 , P, R 3 and R 4 are as defined for compounds of formula (IA);
  • the compounds of formula (IA) may exist in different geometric or optical isomers or tautomeric forms. Other than the chiral configuration at the asymmetric carbon indicated, this invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds. The invention also covers N-oxides and salts.
  • the compounds of the invention may contain one or more additional asymmetric carbon atoms and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such.
  • Alkyl groups can be in the form of a straight or branched chain and are, for example, methyl, ethyl, propyl, prop-2-yl, butyl, but-2-yl, 2 -methyl-prop -1-yl or 2-methyl-prop-2- yl.
  • the alkyl groups are preferably Ci-C 6 , more preferably Q-C4, most preferably Q-C3 alkyl groups. Where an alkyl moiety is said to be substituted, the alkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Alkylene groups can be in the form of a straight or branched chain and are, for example, -CH 2 -, -CH2-CH2-, -CH(CH 3 )-, -CH2-CH2-CH2-, -CH(CH 3 )-CH 2 -, or -CH(CH 2 CH 3 )-.
  • the alkylene groups are preferably C -C3, more preferably C 1 -C 2 , most preferably Ci alkylene groups.
  • Alkenyl groups can be in the form of straight or branched chains, and can be, where appropriate, of either the (E)- or (Z)-configuration. Examples are vinyl and allyl.
  • the alkenyl groups are preferably C 2 -C6, more preferably C 2 -C4, most preferably C 2 -C3 alkenyl groups.
  • Alkynyl groups can be in the form of straight or branched chains. Examples are ethynyl and propargyl.
  • the alkynyl groups are preferably C 2 -C6, more preferably C 2 -C4, most preferably C 2 -C3 alkynyl groups.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Haloalkyl groups are alkyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, difluoromethyl, trifluoromethyl, chlorodifluoromethyl or 2,2,2-trifluoro-ethyl.
  • Haloalkenyl groups are alkenyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, 2,2-difluoro-vinyl or 1 ,2-dichloro-2-fluoro-vinyl.
  • Haloalkynyl groups are alkynyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, l-chloro-prop-2-ynyl.
  • Cycloalkyl groups or carbocyclic rings can be in mono- or bi-cyclic form and are, for example, cyclopropyl, cyclobutyl, cyclohexyl and bicyclo[2.2.1]heptan-2-yl.
  • the cycloalkyl groups are preferably C3-C8, more preferably C3-C6 cycloalkyl groups.
  • the cycloalkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Aryl groups are aromatic ring systems which can be in mono-, bi- or tricyclic form. Examples of such rings include phenyl, naphthyl, anthracenyl, indenyl or phenanthrenyl. Preferred aryl groups are phenyl and naphthyl, phenyl being most preferred. Where an aryl moiety is said to be substituted, the aryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Heteroaryl groups are aromatic ring systems containing at least one heteroatom and consisting either of a single ring or of two or more fused rings.
  • single rings will contain up to three heteroatoms and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulfur.
  • monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (e.g.
  • bicyclic groups include purinyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl and benzothiazolyl.
  • Monocyclic heteroaryl groups are preferred, pyridyl being most preferred. Where a heteroaryl moiety is said to be substituted, the heteroaryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Heterocyclyl groups or heterocyclic rings are defined to include heteroaryl groups and in addition their unsaturated or partially unsaturated analogues.
  • monocyclic groups include isoxazolyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, [l,3]dioxolanyl, piperidinyl, piperazinyl, [l,4]dioxanyl, and morpholinyl or their oxidised versions such as 1 -oxo-thietanyl and 1,1-dioxo-thietanyl.
  • bicyclic groups examples include 2,3-dihydro-benzofuranyl, benzo[l,4]dioxolanyl, benzo[l,3]dioxolanyl, chromenyl, and 2,3- dihydro-benzo[l,4]dioxinyl.
  • a heterocyclyl moiety is said to be substituted, the heterocyclyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Preferred values of P, A 1 , A 2 , A 3 , A 4 , G 1 , Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are, in any combination, as set out below.
  • P is PI, or a heterocycle selected from HI to H9
  • k 0, 1 or 2.
  • no more than two of A 1 , A 2 , A 3 and A 4 are nitrogen, more preferably no more than one of A 1 , A 2 , A 3 and A 4 is nitrogen.
  • a 1 is C-H or C-R 5 , most preferably A 1 is C-R 5 .
  • a 2 is C-H or C-R 5 , most preferably A 2 is C-H.
  • a 3 is C-H or C-R 5 , most preferably A 3 is C-H.
  • A is C-H or C-R , most preferably A is C-H.
  • IInn c one preferred group of compounds A 1 is C-R 5 , A 2 is C-H, A 3 is C-H or nitrogen and A 4 is C-H or nitrogen.
  • a 1 is C-R 5 , A 2 is C-H, A 3 is C-H and A 4 is C-H.
  • G 1 is oxygen
  • R 1 is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl-, more preferably hydrogen, methyl or ethyl, most preferably hydrogen.
  • R 2 is CpCgalkyl or CpCgalkyl substituted by one to five R 6 , C 3 -Ci 0 cycloalkyl or C 3 -
  • R 11 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, cyclopropyl, cyclopropyl-methyl, cyclobutyl, cyclobutyl-methyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R 12 , or R 11 is pyridyl-methyl- or pyridyl-methyl- substituted by one to three R 12 ; and each R 12 is independently fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, cyano or methoxy.
  • R 2 is Ci-C 8 alkyl or Q-Qalkyl substituted by one to five R 6 , C 3 -Ci 0 cycloalkyl or C 3 -Ciocycloalkyl substituted by one to five R 7 , aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Ci-C 4 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 , d-dalkylaminocarbonyl-d-d alkylene, d- dhaloalkylaminocarbonyl-d-d alkylene, -dcycloalkyl-aminocarbony
  • each aryl group is a phenyl group and each heterocyclyl group is independently selected from pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl,
  • R 2 is d-dalkyl or Ci-Cgalkyl substituted by one to five R 6 , C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R 7 , aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-d-dalkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 , Ci-Cgalkylaminocarbonyl-Ci-C4 alkylene, d- Cghaloalkylaminocarbonyl-Crd alkylene, C3-Cgcycloalkyl-aminocarbonyl-C
  • each aryl group is a phenyl group and each heterocyclyl group is selected from 1 ,2,3 triazolyl, 1 ,2,4 triazolyl, tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, tetrahydrothiophenyl, isoxazolinyl, pyridyl, tetrahydrofuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo- thietanyl.
  • R 2 is d-dalkyl or d-dalkyl substituted by one to five R 6 , C 3 - docycloalkyl or d-d 0 cycloalkyl substituted by one to five R 7 , aryl-d-dalkylene- or aryl-d- C 4 alkylene- wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-d-dalkylene- or heterocyclyl-d-dalkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 , d- dalkylaminocarbonyl-d-d alkylene, d-dhaloalkylaminocarbonyl-d-d alkylene, d-dcycloalkyl- aminocarbonyl-d-d alkylene, or
  • R 2 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 6 , C3-Ciocyclo- alkyl or C3-Ciocycloalkyl substituted by one to five R 7 , phenyl-Ci-C 4 alkylene- or phenyl-Ci-C 4 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 4 alkylene- or pyridyl-Cr
  • R 2 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 6 , C3-Ciocyclo- alkyl or C3-Ciocycloalkyl substituted by one to five R 7 , phenyl-Ci-C 4 alkylene- or phenyl-Ci-C 4 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 4 alkylene- or pyridyl-Cr
  • R is Q-Cgalkyl or Q-Cgalkyl substituted by one to three halogen atoms, C 3 -Ci 0 cycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one or two groups independently selected from fluoro and methyl, phenyl-Ci-C 4 alkylene- or phenyl-Ci-C 4 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 4 alkylene- or pyridyl-Ci-C 4 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , thietanyl, oxo-thietanyl, dioxo-thietanyl, Q- Cgalkylaminocarbonyl-methylene, Ci-Cghaloalkylaminocarbonyl-methylene, C 3 -Cgcycloalkyl
  • R is Ci-C 6 alkyl or Ci-C 6 alkyl substituted by one to five R 6 , for example ethyl-, butyl-, but-2-yl-, 3-bromo-propyl-, 2,2,2-trifluoro-ethyl-, 3,3,3- trifluoro-propyl-, 2-methoxy-ethyl-, and l-methoxy-prop-2-yl-.
  • a group of preferred compounds are those wherein R 2 is C 3 -Cgcycloalkyl or C 3 -C 8 cycloalkyl substituted by one to five R 7 , for example cyclobutyl-, 2-fluoro-cyclopropyl and 2-methyl-cyclohex-l -yl-.
  • R 2 is aryl-Ci-C 2 alkylene- or aryl-Q- C 2 alkylene- wherein the aryl moiety is substituted by one to five R 8 , for example phenyl-methyl-, 1 - phenyl-eth-l-yl-, 2-phenyl-eth-l -yl-, (3-chloro-phenyl)-methyl-, (2-fluoro-phenyl)-methyl-, (4-methoxy- phenyl)-methyl-, (2-trifluoromethyl-phenyl)-methyl-, and (2-trifluoromethoxy-phenyl)-methyl-.
  • R 2 is heterocyclyl-Ci-C 2 alkylene- or heterocyclyl-Ci-C 2 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , for example (pyrid-2-yl)-methyl-, (pyrid-3-yl)-methyl-, (2-chloro-pyrid-5-yl)-methyl-, (1 -methyl- lH-imidazol-4-yl)- methyl-, (furan-2-yl)-methyl-, 2-(thiophen-2'-yl)-eth-l -yl-, 2-(indol-3'-yl)-eth-l-yl-, (lH-benzimidazol-2- yl)-methyl-, (oxetan-2-yl)-methyl-, (tetrahydrofuran-2-yl)-methyl-, 2-([l',3']dioxolan-2'-
  • a group of preferred compounds are those wherein R 2 is heterocyclyl-Ci-C 2 alkylene- or heterocyclyl-Ci-C 2 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 in which the heterocyclyl group is selected from 1,2,3 triazolyl, 1,2,4 triazolyl, tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, tetrahydrothiophenyl, isoxazolinyl, pyridyl, tetrahydrofuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo-thietanyl, preferably the heterocyclyl group is selected from thietanyl, oxo-thietanyl and dioxo-thietany
  • a group of preferred compounds are those wherein R 2 is heteroaryl-Ci-C 2 alkylene- or heteroaryl- Ci-C 2 alkylene- wherein the heteroaryl moiety is substituted by one to five R 8 .
  • R 2 is aryl or aryl substituted by one to five R 8 , for example 2-chloro-phenyl-, 3-fluoro-phenyl-, 2-methyl-phenyl-, 2-chloro-6-methyl-phenyl-, 2- trifluoromethyl-phenyl-, and 2,4-dimethoxy-phenyl-.
  • R 2 is heterocyclyl or heterocyclyl substituted by one to five R 8 , for example 3-methyl-pyrid-2-yl-, 1,3 -dimethyl- lH-pyrazol-5-yl-, 4-methyl-thiazol-2- yl-, 5-methyl-thiadiazol-2-yl-, quinolin-2-yl-, quinolin-5-yl-, benzothiazol-6-yl-, 4-methyl-benzothiazol- 2-yl-, thietan-3-yl-, l -oxo-thietan-3-yl-, l,l -dioxo-thietan-3-yl-, and 3 -methyl -thietan-3-yl-, more preferably R 2 is oxetanyl, thietanyl, oxo-thietanyl or dioxo-thietanyl each optionally substituted by one to five R 8
  • a group of preferred compounds are those wherein R 2 is heterocyclyl- or heterocyclyl substituted by one to five R 8 in which the heterocyclyl group is selected from 1,2,3 triazolyl, 1,2,4 triazolyl, tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, tetrahydrothiophenyl, isoxazolinyl, pyridyl,
  • heterocyclyl group is selected from thietanyl, oxo-thietanyl and dioxo-thietanyl.
  • R 2 is Ci-C 8 alkylaminocarbonyl-Ci-C 4 alkylene, Ci-Cghaloalkylaminocarbonyl-Ci-C alkylene, or C 3 -Cgcycloalkyl-aminocarbonyl-Ci-C alkylene, more preferably Ci-C 4 alkylaminocarbonyl-Ci-C 4 alkylene, Ci-C 4 haloalkylaminocarbonyl-Ci-C 4 alkylene, or C3-C 6 cycloalkyl-aminocarbonyl-Ci-C alkylene, most preferably CrQalkylaminocarbonyl- Ci-C 2 alkylene or Ci-C haloalkylaminocarbonyl-Ci-C 2 alkylene.
  • a group of preferred compounds are those wherein R 2 is group A
  • R is chlorodifluoromethyl or trifluoromethyl, most preferably trifluoromethyl.
  • R 4 is aryl or aryl substituted by one to five R 9 , more preferably aryl substituted by one to three R 9 , more preferably phenyl substituted by one to three R 9 , even more preferably 3,5-dibromo- phenyl-, 3,5-dichloro-phenyl-, 3,5-bis-(trifluoromethyl)-phenyl-, 3,4-dichloro-phenyl-, 3,4,5-trichloro- phenyl- 3-trifluoromethyl-phenyl-, 4-bromo-3,5-dichloro-phenyl or 3-chloro-5-trifluoromethyl-phenyl, most preferably R 4 is 3,5-dichloro-phenyl.
  • each R 5 is independently halogen, cyano, nitro, Q-Cgalkyl, Q-Cghaloalkyl, C r C 8 alkenyl, Q-Cghaloalkenyl, Q-Cgalkoxy-, or Q-Cghaloalkoxy-, more preferably bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, methoxy, difluoromethoxy, or trifluoromethoxy, most preferably methyl.
  • each R 6 is independently halogen, cyano, nitro, hydroxy, Q-Cgalkoxy-, Cp
  • Ci-Cgalkylcarbonyl- Ci-Cgalkoxycarbonyl-, mercapto, Ci-Cgalkylthio-, d- Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-,
  • each R 6 is independently halogen, cyano, nitro, hydroxy, Cp Cgalkoxy-, Ci-Cghaloalkoxy-, mercapto, Ci-Cgalkylthio-, Ci-Cghaloalkylthio-, more preferably bromo, chloro, fluoro, methoxy, or methylthio, most preferably chloro, fluoro, or methoxy.
  • each R 7 is independently halogen or Ci-Cgalkyl, more preferably each R 7 is independently chloro, fluoro or methyl, most preferably fluoro or methyl.
  • each R 8 is independently halogen, cyano, nitro, Q-Cgalkyl, Ci-Cghaloalkyl, Q- Cgalkenyl, C 2 -C 8 haloalkenyl, Q-Qalkynyl, Q-Qhaloalkynyl, hydroxy, Q-Qalkoxy-, Q-Cghaloalkoxy-, mercapto, Ci-Cgalkylthio-, Ci-Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Q- Cgalkylsulfonyl-, Ci-Cghaloalkylsulfonyl-, Ci-Cgalkylcarbonyl-, Ci-Cgalkoxycarbonyl-, aryl or aryl substituted by one to five R 10 , or heterocyclyl or heterocyclyl substituted by one to five R 10 , more preferably each R 8
  • each R 9 is independently halogen, Q-Cgalkyl, Q-Qhaloalkyl, Q-Qalkoxy-, Q- Cghaloalkoxy-, Ci-Cgalkylthio-, or Ci-Cghaloalkylthio-, more preferably bromo, chloro, fluoro, trifluoromethyl, methoxy, or methylthio, most preferably bromo or chloro.
  • each R 10 is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy, more preferably bromo, chloro, fluoro, nitro, or methyl, most preferably chloro, fluoro, or methyl.
  • R 11 is methyl, ethyl or trifluoroethyl.
  • each Z is independently halogen, cyano, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, or Ci-C 4 haloalkoxy, more preferably each Z is independently hydrogen, halogen, methyl, halomethyl, methoxy or halomethoxy.
  • P is PI
  • Q is Ql or Q2;
  • a 1 , A 2 , A 3 and A 4 are independently of each other C-H, C-R 5 , or nitrogen;
  • G 1 is oxygen or sulfur
  • R 1 is hydrogen, Ci-Cgalkyl, Q-Qalkoxy-, Ci-Cgalkylcarbonyl-, or Ci-Cgalkoxycarbonyl-;
  • R 2 is Ci-Cgalkyl or Ci-Cgalkyl substituted by one to five R 6 , C 3 -Ciocycloalkyl or C 3 -Ciocycloalkyl substituted by one to five R 7 , aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Ci-C 4 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 , Ci-C 8 alkylaminocarbonyl-Ci-C 4 alkylene, Q- Cghaloalkylaminocarbonyl-Ci-C4 alkylene, C -Cgcycloalkyl-aminocarbony
  • R J is Ci-Cghaloalkyl
  • R 4 is aryl or aryl substituted by one to five R 9 , or heteroaryl or heteroaryl substituted by one to five R 9 ; each R 5 is independently halogen, cyano, nitro, Q-Cgalkyl, Ci-Cghaloalkyl, Q-Cgalkenyl, C r
  • each R 6 is independently halogen, cyano, nitro, hydroxy, Ci-Cgalkoxy-, Ci-Cghaloalkoxy-, d-
  • each R 7 is independently halogen or d-Cgalkyl
  • each R 8 and R 9 is independently halogen, cyano, nitro, CpCgalkyl, Ci-Cghaloalkyl, C 2 -Cgalkenyl, C 2 - Cghaloalkenyl, C 2 -Cgalkynyl, C 2 -Cghaloalkynyl, hydroxy, Q-Cgalkoxy-, Ci-Cghaloalkoxy-, mercapto, Cp Cgalkylthio-, Ci-Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, Q- Cghaloalkylsulfonyl-, Ci-Cgalkylcarbonyl-, Ci-Cgalkoxycarbonyl-, aryl or aryl substituted by one to five R 10 , or heterocyclyl or heterocyclyl substituted by one to five R 10
  • each R 10 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy-, or Q- C 4 haloalkoxy-;
  • R 11 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, cyclopropyl, cyclopropyl-methyl, cyclobutyl, cyclobutyl-methyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R 12 , or R 11 is pyridyl-methyl- or pyridyl -methyl- substituted by one to three R 12 ;
  • each R 12 is independently fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, cyano or methoxy; or a salt or N-oxide thereof.
  • a group of preferred compounds are those wherein
  • a 1 is C-R 5 , A 2 is C-H, A 3 is C-H or nitrogen and A 4 is C-H or nitrogen;
  • G 1 is oxygen
  • R 1 is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl-;
  • R 2 is CpCgalkyl or Q-Cgalkyl substituted by one to five R 6 , C 3 -Ci 0 cycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 7 , aryl-Ci-C 4 alkylene- or aryl-Ci-C 4 alkylene- wherein the aryl moiety is substituted by one to five R 8 , heterocyclyl-Ci-C 4 alkylene- or heterocyclyl-Ci-C 4 alkylene- wherein the heterocyclyl moiety is substituted by one to five R 8 , aryl or aryl substituted by one to five R 8 , heterocyclyl or heterocyclyl substituted by one to five R 8 , Ci-C 8 alkylaminocarbonyl-Ci-C 4 alkylene, Q- Cghaloalkylaminocarbonyl-Ci-C4 alkylene, C -C 8 cycloalkyl-
  • each aryl group is a phenyl group and each heterocyclyl group is selected from pyridyl, tetrahydrofuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo- thietanyl;
  • R 3 is Ci-C 8 haloalkyl
  • R 4 is phenyl substituted by one to three R 9 ;
  • R 5 is independently halogen, cyano, nitro, Q-Cgalkyl, Ci-Cghaloalkyl, Q-Cgalkenyl, Ci-Cghalo- alkenyl, Q-Cgalkoxy-, or Ci-Cghaloalkoxy-;
  • each R 6 is independently halogen, cyano, nitro, hydroxy, CpCgalkoxy-, Ci-Cghaloalkoxy-, mercapto, Ci-Cgalkylthio-, Ci-Cghaloalkylthio-;
  • each R 7 is independently chloro, fluoro or methyl
  • each R 8 is independently halogen, cyano, nitro, CpCgalkyl, Ci-Cghaloalkyl, d-Cgalkoxy-, d- Cghaloalkoxy-;
  • each R 9 is independently halogen, CpCgalkyl, Ci-Cghaloalkyl, Q-Cgalkoxy-, Ci-Cghaloalkoxy-, Ci-Cgalkylthio-, or Ci-Cghaloalkylthio-;
  • a 1 is C-R 5 , A 2 is C-H, A 3 is C-H and A 4 is C-H;
  • G 1 is oxygen
  • R is hydrogen, methyl or ethyl
  • R 2 is Ci-Cgalkyl or d-Cgalkyl substituted by one to five R 6 , C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R 7 , phenyl-Ci-C 4 alkylene- or phenyl-Ci-C 4 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 4 alkylene- or pyridyl-Ci-C 4 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , oxetanyl or oxetanyl substituted by one to five R 8 , thietanyl-Ci-C4 alkylene or thietanyl-Ci-C4 alkylene wherein the thietanyl moiety is substituted by one to five R 8 , oxo- thietanyl-
  • R 4 is 3,5-dibromo-phenyl-, 3,5-dichloro-phenyl-, 3,5-bis-(trifluoromethyl)-phenyl-, 3,4-dichloro- phenyl-, 3,4,5-trichloro-phenyl-, 3-trifluoromethyl-phenyl-, 4-bromo-3,5-dichloro-phenyl or 3-chloro-5- trifluoromethyl-phenyl;
  • R 5 is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, methoxy, difluoromethoxy, or trifluoromethoxy;
  • each R 6 is independently bromo, chloro, fluoro, methoxy, or methylthio
  • each R 7 is independently fluoro or methyl
  • each R 8 is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy;
  • R 11 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, cyclopropyl, cyclopropyl-methyl, cyclobutyl, cyclobutyl-methyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R 12 , or R 11 is pyridyl-methyl- or pyridyl-methyl- substituted by one to three R 12 ;
  • each R 12 is independently fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, cyano or methoxy.
  • P is PI
  • a 1 is C-R 5 , A 2 is C-H, A 3 is C-H and A 4 is C-H;
  • G 1 is oxygen
  • R 1 is hydrogen
  • R 2 is Ci-C 8 alkyl or Q-Cgalkyl substituted by one to three halogen atoms, C 3 -Ci 0 cycloalkyl or C 3 - Ciocycloalkyl substituted by one or two groups independently selected from fluoro and methyl, phenyl- Ci-C 4 alkylene- or phenyl-Ci-C 4 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 4 alkylene- or pyridyl-Ci-C 4 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , thietanyl, oxo-thietanyl, dioxo-thietanyl, Ci-C alkylaminocarbonyl-Ci-C alkylene, Q- C haloalkylaminocarbonyl-Ci-C alkylene, C3-C cycl
  • R is trifluoromethyl
  • R 4 is 3,5-dichloro-phenyl
  • R 5 is methyl
  • each R 8 is independently bromo, chloro, fluoro, cyano or methyl
  • R 11 is methyl, ethyl or trifluoroethyl.
  • P is PI ;
  • a 1 is C-R 5 , A 2 is CH, A 3 is CH and A 4 is CH;
  • G 1 is oxygen
  • R 1 is hydrogen
  • R 2 is C 2 -C 6 alkyl or C 2 -Cealkyl substituted by one to three halogen atoms, C3-Cgcycloalkyl or C3- Cgcycloalkyl substituted by one or two groups independently selected from fluoro and methyl, phenyl-d- C 2 alkylene- or phenyl-C i-C 2 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl- Ci-C 2 alkylene- or pyridyl-Ci-C 2 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , thietanyl, oxo-thietanyl, dioxo-thietanyl, Ci-C 4 alkylaminocarbonyl-Ci-C 2 alkylene or Q- C 4 haloalkylaminocarbonyl-Ci-C 2 alkylene, or group
  • R is trifluoromethyl
  • R 4 is 3,5-dichloro-phenyl
  • R 5 is methyl
  • each R 8 is independently bromo, chloro, fluoro, cyano or methyl
  • R 11 is methyl, ethyl or trifluoroethyl.
  • the present invention provides compounds of formula (IAa)
  • G 1 , R 1 , R 2 , R 3 , R 4 and R 5 are as defined for compounds of formula (IA); or a salt or N-oxide thereof.
  • the preferences for G 1 , R 1 , R 2 , R 3 , R 4 and R 5 are the same as the preferences set out for the corresponding substituents of compounds of the formula (IA).
  • the present invention provides a mixture comprising a compound of formula (IAa) as defined above and a compound of formula (IBa)
  • G 1 , R 1 , R 2 , R 3 , R 4 and R 5 are as defined for compounds of formula (IA); or a salt or N-oxide thereof.
  • the preferences for G 1 , R 1 , R 2 , R 3 , R 4 and R 5 are the same as the preferences set out for the corresponding substituents of compounds of the formula (IA).
  • the present invention provides a mixture comprising a compound of formula (IAb) as defined above and a compound of formula (IBb)
  • G 1 , R 1 , R 2 , R 3 , R 4 and R 5 and preferences thereof are as defined for compounds of formula (IA); and wherein the mixture is enriched for compounds of formula (IAb).
  • R 3 , R 4 and R 5 are as defined for compounds of formula (IA) and Het is selected from HI to H9 as defined for compounds of formula (IA); or a salt or N-oxide thereof.
  • the preferences for R 3 , R 4 , R 5 , and Het are the same as the preferences set out for the corresponding substituents of compounds of the formula (IA).
  • the present invention provides a mixture comprising a compound of formula (IAc) as defined above and a compound of formula (IBc)
  • R 3 , R 4 and R 5 are as defined for compounds of formula (IA) and Het is selected from HI to H9 as defined for compounds of formula (IA) and wherein the mixture is enriched for compounds of formula (IAc).
  • the preferences for R 3 , R 4 , R 5 , and Het are the same as the preferences set out for the
  • R 3 , R 4 and R 5 are as defined for compounds of formula (IA) and Het is selected from HI to H9 as defined for compounds of formula I; or a salt or N-oxide thereof.
  • the preferences for R 3 , R 4 , R 5 , and Het are the same as the preferences set out for the corresponding substituents of compounds of the formula (IA).
  • the present invention provides a mixture comprising a compound of formula (IAd) as de rmula (IBd)
  • R 3 , R 4 and R 5 and preferences thereof are as defined for compounds of formula (IA) and Het is selected from HI to H9 as defined for compounds of formula (IA) and wherein the mixture is enriched for compounds of formula (IAd).
  • Q A , A 1 , A 2 , A 3 , and A 4 are as defined for a compound of formula (IA), G 1 is oxygen, and R is hydroxy, Ci-Ci 5 alkoxy or halogen, such as bromo, chloro or fluoro; or a salt or N-oxide thereof.
  • the preferences for Q A , A 1 , A 2 , A 3 , and A 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • R is hydroxy, Q-Cealkoxy or chloro.
  • the invention also provides a mixture comprising a compound of formula (IIA) as defined above and a compound of formula (IIB)
  • a 1 , A 2 , A 3 , and A 4 and preferences thereof are as defined for a compound of formula (IA),
  • Q B is as defined for a compound of formula (IB)
  • G 1 is oxygen
  • R is hydroxy, Ci-Ci 5 alkoxy (e.g. C r C 6 alkoxy) or halogen, such as bromo, chloro or fluoro, preferably hydroxy, Ci-C 6 alkoxy or chloro, and wherein the mixture is enriched for compounds of formula (IIA).
  • One group of compounds of formula (IIA) are compounds of formula (IIAa)
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for a compound of formula (IA), G 1 is oxygen, and R is hydroxy, CpCealkoxy or halogen, such as bromo, chloro or fluoro; or a salt or N-oxide thereof.
  • the preferences for A 1 , A 2 , A 3 , A 4 , R 3 and R 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • R is hydroxy, CpCealkoxy or chloro.
  • the invention also provides a mixture comprising a compound of formula (IIAa) as defined above and a compound of formula (IIBa)
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 and preferences thereof are as defined for a compound of formula (IA), G 1 is oxygen, and R is hydroxy, CpCealkoxy or halogen, such as bromo, chloro or fluoro, and wherein the mixture is enriched for compounds of formula (IIAa).
  • a further group of compounds of formula IIA are compounds of formula (IIAb)
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for a compound of formula (IA), G 1 is oxygen, and R is hydroxy, CpCealkoxy or halogen, such as bromo, chloro or fluoro; or a salt or N-oxide thereof.
  • the preferences for A 1 , A 2 , A 3 , A 4 , R 3 and R 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • R is hydroxy, CpCealkoxy or chloro.
  • the invention also provides a mixture comprising a compound of formula (IIAb) as defined above and a compound
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 and preferences thereof are as defined for a compound of formula (IA), G 1 is oxygen, and R is hydroxy, CpCealkoxy or halogen, such as bromo, chloro or fluoro, and wherein the mixture is enriched for compounds of formula (IIAb).
  • a further group of compounds of formula (IIA) are compounds of formula (IIAc)
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for a compound of formula (IA), G 1 is oxygen, and R hydroxy, CpCealkoxy or halogen, such as bromo, chloro or fluoro; or a salt or N-oxide thereof.
  • the preferences for A 1 , A 2 , A 3 , A 4 , R 3 and R 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • R is hydroxy, CpCealkoxy or chloro.
  • the invention also provides a mixture comprising a compound of formula (IIAc) as defined above and a compound of formula (IIBc)
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 and preferences thereof are as defined for a compound of formula (IA), G 1 is oxygen, and R is hydroxy, Ci-C 6 alkoxy or halogen, such as bromo, chloro or fluoro, and wherein the mixture is enriched for compounds of formula (IIAc).
  • R is hydroxy, Ci-C 6 alkoxy or chloro.
  • a further group of novel intermediates are compounds of formula ( ⁇ )
  • Q A , A 1 , A 2 , A 3 , and A 4 are as defined for a compound of formula (IA), and X is a leaving group such as halogen, CpCgalkoxy, Ci-Cgalkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, Ci-Cgarylsulfonyloxy, optionally substituted Ci-Cgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g.
  • X B is -N 2 + CI " , -N 2 + BF 4 " , -N 2 + Br “ , -N 2 + PF 6 " ), phosphonate esters (e.g. -OP(0)(OR) 3 ⁇ 4 wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride; or a salt or N-oxide thereof.
  • the preferences for Q A , A 1 , A 2 , A 3 , and A 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula ( ⁇ ) as defined above and a compound of formula (IIIB)
  • a 1 , A 2 , A 3 , and A 4 and preferences thereof are as defined for a compound of formula (IA), Q B is as defined for compounds of formula (IB) and X B is a leaving group such as halogen, CpCgalkoxy, C r Cgalkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, Ci-Cgarylsulfonyloxy, optionally substituted Cp Cgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g.
  • X B is -N 2 + CI " , -N 2 + BF 4 " , -N 2 + Br “ , - N 2 + PF 6 " ), phosphonate esters (e.g. -OP(0)(OR) 2; wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride, and wherein the mixture is enriched for compounds of formula (IIIA).
  • phosphonate esters e.g. -OP(0)(OR) 2; wherein R is methyl or ethyl
  • R is methyl or ethyl
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for a compound of formula (IA), and X is as defined for compounds of formula (IIIA).
  • the preferences for A 1 , A 2 , A 3 , A 4 , R 3 and R 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (IIIAa) as defined above and a compound
  • a further group are compounds of formula (IIIAb)
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for a compound of formula (IA), and X is as defined for compounds of formula (IIIA).
  • the preferences for A 1 , A 2 , A 3 , A 4 , R 3 and R 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (IIIAb) as defined above and a compound
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 and preferences thereof are as defined for a compound of formula (IA), and X B is as defined for compounds of formula (IIIA), and wherein the mixture is enriched for compounds of formula (IIIAb).
  • a further group of compounds of formula (IIIA) are compounds of formula (IIIAc)
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for a compound of formula (IA) and X is as defined for compounds of formula (IIIA).
  • the preferences for A 1 , A 2 , A 3 , A 4 , R 3 and R 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (IIIAc) as defined above and a compound of formula (IIIBc)
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for compounds of formula (IA), Px is P as defined above (for the compound of formula (IA)), a leaving group X B , such as halogen, d-Cgalkoxy, Cp
  • the invention also provides a mixture comprising a compound of formula (XXVA) as defined above and a compound of formula (XXVB)
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 and preferences thereof are as defined for compounds of formula (IA),
  • Px is P as defined above, a leaving group X B , such as halogen, Q-Cgalkoxy, CpCgalkylsulfonyloxy, C r Cghaloalkylsulfonyloxy, Ci-C 8 arylsulfonyloxy, optionally substituted Q-Cgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g.
  • X B is -N 2 + CI " , -N 2 + BF 4 " , -N 2 + Br “ , -N 2 + PF 6 " ), phosphonate esters (e.g. -OP(0)(OR) 2; wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride, or C(0)R wherein R is halogen, OH or Ci-Ci 5 alkoxy, and wherein the mixture is enriched for compounds of formula (XXVA).
  • phosphonate esters e.g. -OP(0)(OR) 2; wherein R is methyl or ethyl
  • R is methyl or ethyl
  • R preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazon
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for compounds of formula (IA), and X is as defined for the compound of formula (XXVA).
  • the preferences for A 1 , A 2 , A 3 , A 4 , R 3 , and R 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (XXVAa) as defined above and a compound of formula (XXVBa)
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 and preferences thereof are as defined for compounds of formula (IA), and X B is as defined for the compound of formula (XXVAa), and wherein the mixture is enriched for compounds of formula (XXVAa).
  • a 1 , A 2 , A 3 , A 4 , R 1 , R 2 , R 3 and R 4 are as defined for compounds of formula (IA).
  • the preferences for A 1 , A 2 , A 3 , A 4 , R 1 , R 2 , R 3 , and R 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (XXVAb) as defined above and a comp
  • a 1 , A 2 , A 3 , A 4 , R 1 , R 2 , R 3 and R 4 and preferences thereof are as defined for compounds of formula (IA), and X B is as defined for the compound of formula (XXVa), and wherein the mixture is enriched for compounds of formula (XXVAb).
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula I.
  • the preferences for A 1 , A 2 , A 3 , A 4 , R 3 , R 4 and heterocyclyl are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (XXVAc) as defined above and a compound of formula (XXVBc) (XXVBc)
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 and preferences thereof are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula (IA), and wherein the mixture is enriched for compounds of formula (XXVAc).
  • R and R are as defined for the compounds of formula (IA), or a salt or N-oxide thereof.
  • the preferences for R 3 and R 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • a preferred group of compounds of formula (XXIIIA) are those wherein R 3 is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 .
  • the invention also provides a mixture comprising a compound of formula (XXIIIA) as defined above and a compound of formula (XXIIIB)
  • R 3 and R 4 and preferences thereof are as defined for the compounds of formula (IA), e.g. R 3 is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 , and wherein the mixture is enriched for compounds of formula (XXIIIA).
  • halogen optionally substituted by halogen, C 1 -C4 alkyl or a leaving group, such as halogen, d-Cgalkoxy, Ci-Cgalkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, Cp Cgarylsulfonyloxy, optionally substituted Ci-Cgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g. is -N 2 + CI " , -N 2 + BF 4 " , -N 2 + Br " , -N 2 + PF 6 _) , phosphonate esters (e.g.
  • R is methyl or ethyl
  • R is methyl or ethyl
  • a preferred group of compounds of formula (XXVIA) are those wherein R 3 is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 .
  • the invention also provides a mixture comprising a compound of formula (XXVIA) as defined above and a compound of formula (XXVIB)
  • R and R and preferences thereof are as defined for compounds of formula (IA), e.g. R is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 , and X is a tin derivative, e.g. SnR 13 3 wherein each R 13 is independently Ci-C 6 alkyl, a boron derivative, e.g. BF 3 , B(OH) 2 or B(OR) 2 , wherein each R is independnetly Ci-C 6 -alkyl, Ci-C 6 -cycloalkyl or optionally substituted Ci-C 6 -cycloalkyl, e.g.
  • halogen optionally substituted by halogen, Q-C4 alkyl or Ci-C 4 haloalkyl, a leaving group, such as halogen, Q-Cgalkoxy, Q- Cgalkylsulfonyloxy, Q-Cghaloalkylsulfonyloxy, Ci-C 8 arylsulfonyloxy, optionally substituted C r Cgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g. -N 2 + CI " , -N 2 + BF 4 " , -N 2 + Br " , -N 2 + PF 6 " phosphonate esters (e.g.
  • R and R and preferences thereof are as defined for compounds of formula (IA), e.g. R is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 , and X is CI, Br or I, or a salt or N-oxide thereof.
  • Compounds of formula XXVIA' are a preferred group of compounds of formula XXVIA.
  • the invention also provides a mixture comprising a compound of formula (XXVIA') as defined above and a compound of formula (XXVIB')
  • R and R and preferences thereof are as defined for compounds of formula (IA), e.g. R is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 , and X is CI, Br or I, and wherein the mixture is enriched for compounds of formula (XXVIA').
  • R 3 and R 4 and preferences thereof are as defined for compounds of formula (IA), and X is as defined for compounds of formula (XXVIA), or a salt or N-oxide thereof.
  • a preferred group of compounds of formula (XXVIIA) are those wherein R 3 is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 .
  • the invention also provides a mixture comprising a compound of formula (XXVIIA) as defined above and a compound of formula (XXVIIB)
  • R and R and preferences thereof are as defined for compounds of formula I, e.g. R is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 , and X is as defined for compounds of formula (XXVIA), and wherein the mixture is enriched for compounds of formula (XXVIIA).
  • R 3 and R 4 and preferences thereof are as defined for compounds of formula (IA), and X is CI, Br or I, or a salt or N-oxide thereof.
  • a preferred group of compounds of formula (XXVIIA') are those wherein R 3 is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 .
  • Compounds of formula XXVIIA' are a preferred group of compounds of formula XXVIA.
  • the invention also provides a mixture comprising a compound of formula (XXVIIA') as defined above and a compound of formula (XXVIIB')
  • R 3 and R 4 and preferences thereof are as defined for compounds of formula (IA), e.g. R 3 is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 , and X is CI, Br or I, and wherein the mixture is enriched for compounds of formula (XXVIIA').
  • R and R and preferences thereof are as defined for compounds of formula (IA), or a salt or N- oxide thereof.
  • a preferred group of compounds of formula (XXXVIA) are those wherein R 3 is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 .
  • the invention also provides a mixture comprising a compound of formula (XXXVIA) as defined above and a compound of formula (XXXVIB) (XXXVI B)
  • R and R and preferences thereof are as defined for compounds of formula (IA), e.g. R is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 , and wherein the mixture is enriched for compounds of formula (XXXVIA).
  • R 3 and R 4 and preferences thereof are as defined for compounds of formula (IA), or a salt or N- oxide thereof.
  • a preferred group of compounds of formula (XXXVIIA) are those wherein R 3 is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 .
  • the invention also provides a mixture comprising a compound of formula (XXXVIIA) as defined above and a compound of formula (XXXVIIB)
  • R 3 and R 4 and preferences thereof are as defined for compounds of formula (IA), e.g. R 3 is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 , and wherein the mixture is enriched for compounds of formula (XXXVIIA).
  • Another group of novel intermediates are com ounds of formula (XXXVIIIA) (XXXVIIIA) wherein R 3 and R 4 and preferences thereof are as defined for compounds of formula (IA), and X is as defined for compounds of formula (XXVIA), or a salt or N-oxide thereof.
  • a preferred group of compounds of formula (XXXVIIIA) are those wherein R 3 is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 .
  • the invention also provides a mixture comprising a compound of formula (XXXVIIIA) as defined above and a compound of formula (XXXVIIIB)
  • R 3 and R 4 and preferences thereof are as defined for compounds of formula (IA), e.g. R 3 is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 , and X is as defined for compounds of formula (XXVIA), wherein the mixture is enriched for compounds of formula (XXXVIIIA).
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and P are as defined for compounds of formula (IA), or a salt or N-oxide thereof.
  • the preferences for R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and P are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (LA) as defined above and a compound of fo
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and P and preferences thereof are as defined for compounds of formula (IA), and wherein the mixture is enriched for compounds of formula (LA).
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are as defined for the compound of formula (IA) and Px is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof.
  • the preferences for R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and Px (when Px is P) are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
  • the invention also provides a mixture comprising a compound of formula (LXA) as defined above and a compound of formula (LXB)
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and preferences thereof are as defined for the compound of formula (IA) and Px is as defined for the compound of formula (XXVA), and wherein the mixture is enriched for compounds of formula (LXA).
  • the compound of formula (LXA) includes compounds of formula (LXA') which can exist in quilibrium with compounds of formula (LXA)
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are as defined for the compound of formula (IA) and Px is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof.
  • the preferences for R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and Px (when Px is P) are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
  • One group of compounds of formula (LXA) are compounds of (LXAa)
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are as defined for the compound of formula (IA) and X B is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof.
  • the preferences for R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
  • the invention also provides a mixture comprising a compound of formula (LXAa) as defined above and a compound of formula (LXBa) wherein R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and preferences thereof are as defined for the compound of formula (IA) and X B is as defined for the compound of formula (XXVA), and wherein the mixture is enriched for compounds of formula (LXAa).
  • Another group of compounds of formula (LXA) are compounds of (LXAb)
  • R 1 , R 2 , R 3 , R 4 , A 1 , A 2 , A 3 and A 4 are as defined for the compound of formula (IA), or a salt or N-oxide thereof.
  • the preferences for R 1 , R 2 , R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are the same as the preferences set our for the corresponding substituents of the compound of formula (IA) .
  • the invention also provides a mixture comprising a compound of formula (LXAb) as defined above and a compound of formula (LXBb)
  • R 1 , R 2 , R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and preferences thereof are as defined for the compound of formula (IA), and wherein the mixture is enriched for compounds of formula (LXAb).
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula I.
  • the preferences for A 1 , A 2 , A 3 , A 4 , R 3 , R 4 and heterocyclyl are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (LXAc) as defined above and a compound of formula (LXBc)
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 and preferences thereof are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula (IA), and wherein the mixture is enriched for compounds of formula (LXAc).
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are as defined for the compound of formula (IA) and Px is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof.
  • the preferences for R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and Px (when Px is P) are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
  • the invention also provides a mixture comprising a compound of formula (LIXA) as defined above and a compound of formula (LIXB)
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and preferences thereof are as defined for the compound of formula (IA) and Px is as defined for the compound of formula (XXVA), and wherein the mixture is enriched for compounds of formula (LIXA).
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are as defined for the compound of formula (IA) and X B is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof.
  • the preferences for R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
  • the invention also provides a mixture comprising a compound of formula (LIXAa) as defined above and a compound of formula (LIXBa)
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and preferences thereof are as defined for the compound of formula (IA) and X B is as defined for the compound of formula (XXVA), and wherein the mixture is enriched for compounds of formula (LIXAa).
  • Another group of compounds of formula (LIXA) are compounds of (LIXAb)
  • R 1 , R 2 , R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are as defined for the compound of formula (IA), or a salt or N- oxide thereof.
  • the preferences for R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (LIXAb) as defined above and a compound of formula (LIXBb)
  • R 1 , R 2 , R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and preferences thereof are as defined for the compound of formula (IA), and wherein the mixture is enriched for compounds of formula (LIXAb).
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula I.
  • the preferences for A 1 , A 2 , A 3 , A 4 , R 3 , R 4 and heterocyclyl are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (LIXAc) as defined above and a compound of formula (LIXBc)
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 and preferences thereof are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula (IA), and wherein the mixture is enriched for compounds of formula (LIXAc).
  • R and R are as defined for compounds of formula (IA), or a salt or N-oxide thereof.
  • the preferences for R 3 and R 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (LIIA) as defined above and a compound of formula (LIIB)
  • R 3 and R 4 and preferences thereof are as defined for compounds of formula (IA), and wherein the mixture is enriched for compounds of formula (LIIA).
  • the compound of formula (LIIA) includes compounds of formula (LIIA') which can exist in quilibrium with compounds of formula (LIIA)
  • R 3 and R 4 are as defined for compounds of formula (IA), or a salt or N-oxide thereof.
  • the preferences for R 3 and R 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • R 3 and R 4 are as defined for compounds of formula (IA), and each X independently represents CI, Br or I, or a salt or N-oxide thereof.
  • the preferences for R 3 and R 4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (LIIIA) as defined above and a compound of formula (LIIIB) (LIIIB)
  • R 3 and R 4 and preferences thereof are as defined for compounds of formula (IA), and each X independently represents CI, Br or I, and wherein the mixture is enriched for compounds of formula (LIIIA).
  • R , R , A , A , A and A are as defined for compounds of formula (IA) and Px is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof.
  • the preferences for R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and Px (when Px is P) are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (LVA) as defined above and a compound of formula (LVB)
  • One group of compounds of formula (LVA) are compounds of (LVAa)
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are as defined for the compound of formula (IA) and X B is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof.
  • the preferences for R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
  • the invention also provides a mixture comprising a compound of formula (LVAa) as defined above and a compound of formula (LVBa)
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and preferences thereof are as defined for the compound of formula (IA) and X B is as defined for the compound of formula (XXVA), and wherein the mixture is enriched for compounds of formula (LVAa).
  • Another group of compounds of formula (LVA) are compounds of (LVAb)
  • R 1 , R 2 , R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are as defined for the compound of formula (IA), or a salt or N- oxide thereof.
  • the preferences for R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (LVAb) as defined above and a compound of formula (LVBb)
  • R 1 , R 2 , R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and preferences thereof are as defined for the compound of formula (IA), and wherein the mixture is enriched for compounds of formula (LVAb).
  • Another group of compounds of formula (LVA) are compounds of (LVAc)
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula I.
  • the preferences for A 1 , A 2 , A 3 , A 4 , R 3 , R 4 and heterocyclyl are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (LVAc) as defined above and a compound of formula (LVBc)
  • the invention also provides compounds of formula (LVIA)
  • R 3 , R 4 , A 1 , A 2 , A 3 and A 4 are as defined for compounds of formula (IA) and Px is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof.
  • the preferences for R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and Px (when Px is P) are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (LIXAa) as defined above and a compound of formula (LIXBa)
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and preferences thereof are as defined for the compound of formula (IA) and Px is as defined for the compound of formula (XXVA), and wherein the mixture is enriched for compounds of formula (LVIA).
  • One group of compounds of formula (LVIA) are compounds of (LVIAa)
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are as defined for the compound of formula (IA) and X B is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof.
  • the preferences for R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
  • the invention also provides a mixture comprising a compound of formula (LVIAa) as defined above and a compound of formula (LVIBa) (LVIBa)
  • R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and preferences thereof are as defined for the compound of formula (IA) and X B is as defined for the compound of formula (XXVA), and wherein the mixture is enriched for the compound of formula (LVIAa)
  • Another group of compounds of formula (LVIA) are compounds of (LVIAb)
  • R 1 , R 2 , R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are as defined for the compound of formula (IA), or a salt or N- oxide thereof.
  • the preferences for R 1 , R 2 , R 3 , R 4 , A 1 , A 2 , A 3 , A 4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
  • the invention also provides a mixture comprising a compound of formula (LVIAb) as defined above and a compound of formula (LVIBb)
  • R 1 , R 2 , R 3 , R 4 , A 1 , A 2 , A 3 , A 4 and preferences thereof are as defined for the compound of formula (IA), and wherein the mixture is enriched for compounds of formula (LVIAb).
  • Another group of compounds of formula (LVIA) are compounds of (LVIAc)
  • a 1 , A 2 , A 3 , A 4 , R 3 and R 4 are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula (IA).
  • Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula (IA).
  • the preferences for A 1 , A 2 , A 3 , A 4 , R 3 , R 4 and heterocyclyl are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
  • the invention also provides a mixture comprising a compound of formula (LVIAc) as defined above and a compound of formula (LVIBc)
  • the molar proportion of the enriched compound in the mixture compared to the total amount of both compounds (e.g. the total amount of the compound of formula (IA) and the compound of formula ((IB)) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%. This also applies to the intermediate mixtures described above.
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is CH
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy fluoro
  • Y 1 is CH
  • Y 2 is hydrogen 1 CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0073 is hydrogen 1 bromo CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0074 is hydrogen 1 chloro CH
  • Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0075 is hydrogen 1 cyano CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0076 is hydrogen 1 cyclopropyl CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0077 is hydrogen 1 ethyl CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0078 is hydrogen 1 fluoro CH
  • Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0079 is hydrogen 1 hydrogen CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0080 is hydrogen 1 methoxy CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0081 is hydrogen 1 methyl CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0082 is hydrogen 1 nitro CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0083 is hydrogen 1 trifluoromethoxy CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0084 is hydrogen 1 trifluoromethyl CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0085 is hydrogen difluoromethyl bromo CH
  • Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0086 is hydrogen difluoromethyl chloro CH
  • Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0087 is hydrogen difluoromethyl cyano CH
  • Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0088 is hydrogen difluoromethyl cyclopropyl CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0089 is hydrogen difluoromethyl ethyl CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0090 is hydrogen difluoromethyl fluoro CH
  • Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0091 is hydrogen difluoromethyl hydrogen CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0092 is hydrogen difluoromethyl methoxy CH
  • Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0093 is hydrogen difluoromethyl methyl CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0094 is hydrogen difluoromethyl nitro CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0095 is hydrogen difluoromethyl trifluoromethoxy CH
  • Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0096 is hydrogen difluoromethyl trifluoromethyl CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 trifluoromethyl bromo
  • Y 1 is CH
  • Y 2 is is hydrogen CH
  • Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0098 is hydrogen trifluoromethyl chloro CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0099 is hydrogen trifluoromethyl cyano CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0100 is hydrogen trifluoromethyl cyclopropyl CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0101 is hydrogen trifluoromethyl ethyl CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0102 is hydrogen trifluoromethyl fluoro CH
  • Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0103 is hydrogen trifluoromethyl hydrogen CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0104 is hydrogen trifluoromethyl methoxy CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0105 is hydrogen trifluoromethyl methyl CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0106 is hydrogen trifluoromethyl nitro CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0107 is hydrogen trifluoromethyl trifluoromethoxy CH, Y 3 is CH
  • X 1 is fluoro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0108 is hydrogen trifluoromethyl trifluoromethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0109 is hydrogen 1 bromo CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.01 10 is hydrogen 1 chloro CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0111 is hydrogen 1 cyano CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0112 is hydrogen 1 cyclopropyl CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0113 is hydrogen 1 ethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0114 is hydrogen 1 fluoro CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.01 15 is hydrogen 1 hydrogen CH, Y 3 is CH
  • X 1 is chioro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0116 is hydrogen 1 methoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0117 is hydrogen 1 methyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0118 is hydrogen 1 nitro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.01 19 is hydrogen 1 trifluoromethoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0120 is hydrogen 1 trifluoromethyl CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0121 is hydrogen difluoromethyl bromo CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0122 is hydrogen difluoromethyl chloro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0123 is hydrogen difluoromethyl cyano CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0124 is hydrogen difluoromethyl cyclopropyl CH, Y 3 is CH X 1 is chloro, X 2 is C-Cl, X 3 Y 1 is CH, Y 2 is
  • P.0125 is hydrogen difluoromethyl ethyl CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0126 is hydrogen difluoromethyl fluoro CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0127 is hydrogen difluoromethyl hydrogen CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0128 is hydrogen difluoromethyl methoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0129 is hydrogen difluoromethyl methyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0130 is hydrogen difluoromethyl nitro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X Y 1 is CH
  • Y 2 is
  • P.0131 is hydrogen difluoromethyl trifluoromethoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0132 is hydrogen difluoromethyl trifluoromethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0133 is hydrogen trifluoromethyl bromo CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0134 is hydrogen trifluoromethyl chloro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X Y 1 is CH
  • Y 2 is
  • P.0135 is hydrogen trifluoromethyl cyano CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0136 is hydrogen trifluoromethyl cyclopropyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0137 is hydrogen trifluoromethyl ethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0138 is hydrogen trifluoromethyl fluoro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X Y 1 is CH
  • Y 2 is
  • P.0139 is hydrogen trifluoromethyl hydrogen CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X i Y 1 is CH
  • Y 2 is
  • P.0140 is hydrogen trifluoromethyl methoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0141 is hydrogen trifluoromethyl methyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0142 is hydrogen trifluoromethyl nitro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X Y 1 is CH
  • Y 2 is
  • P.0143 is hydrogen trifluoromethyl trifluoromethoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X i Y 1 is CH
  • Y 2 is
  • P.0144 is hydrogen trifluoromethyl trifluoromethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0145 is chloro 1 bromo CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0146 is chloro 1 chloro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0147 is chloro 1 cyano CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • Y 1 is CH
  • Y 2 is
  • P.0148 is chloro 1 cyclopropyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0149 is chloro 1 ethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0150 is chloro 1 fluoro CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0151 is chloro 1 hydrogen CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 chlorodifluoromethy methoxy
  • Y 1 is CH
  • Y 2 is is chloro 1 CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0153 is chloro 1 methyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0154 is chloro 1 nitro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0155 is chloro 1 trifluoromethoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0156 is chloro 1 trifluoromethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0157 is chloro difluoromethyl bromo CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0158 is chloro difluoromethyl chloro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0159 is chloro difluoromethyl cyano CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0160 is chloro difluoromethyl cyclopropyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0161 is chloro difluoromethyl ethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0162 is chloro difluoromethyl fluoro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X Y 1 is CH
  • Y 2 is
  • P.0163 is chloro difluoromethyl hydrogen CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0164 is chloro difluoromethyl methoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0165 is chloro difluoromethyl methyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0166 is chloro difluoromethyl nitro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0167 is chloro difluoromethyl trifluoromethoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0168 is chloro difluoromethyl trifluoromethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0169 is chloro trifluoromethyl bromo CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0170 is chloro trifluoromethyl chloro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0171 is chloro trifluoromethyl cyano CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0172 is chloro trifluoromethyl cyclopropyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0173 is chloro trifluoromethyl ethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0174 is chloro trifluoromethyl fluoro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0175 is chloro trifluoromethyl hydrogen CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0176 is chloro trifluoromethyl methoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0177 is chloro trifluoromethyl methyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0178 is chloro trifluoromethyl nitro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Br
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0179 is chloro trifluoromethyl trifluoromethoxy CH, Y 3 is CH X 1 is chloro, X 2 is C-Br, X 3 Y 1 is CH, Y 2 is
  • P.0180 is chloro trifluoromethyl trifluoromethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is trifluoromethyl cyano
  • Y 1 is CH
  • Y 2 is chloro CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-F
  • X 3 is Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0217 is chloro 1 bromo CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0218 is chloro 1 chloro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0219 is chloro 1 cyano CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0220 is chloro 1 cyclopropyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0221 is chloro 1 ethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0222 is chloro 1 fluoro CH
  • Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0223 is chloro 1 hydrogen CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0224 is chloro 1 methoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0225 is chloro 1 methyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0226 is chloro 1 nitro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0227 is chloro 1 trifluoromethoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • P.0228 is chloro 1 trifluoromethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0229 is chloro difluoromethyl bromo CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0230 is chloro difluoromethyl chloro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0231 is chloro difluoromethyl cyano CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0232 is chloro difluoromethyl cyclopropyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0233 is chloro difluoromethyl ethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0234 is chloro difluoromethyl fluoro CH, Y 3 is CH X 1 is chloro, X 2 is C-Cl, X 3 Y 1 is CH, Y 2 is
  • P.0235 is chloro difluoromethyl hydrogen CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0236 is chloro difluoromethyl methoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0237 is chloro difluoromethyl methyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0238 is chloro difluoromethyl nitro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0239 is chloro difluoromethyl trifluoromethoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0240 is chloro difluoromethyl trifluoromethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0241 is chloro trifluoromethyl bromo CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0242 is chloro trifluoromethyl chloro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0243 is chloro trifluoromethyl cyano CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0244 is chloro trifluoromethyl cyclopropyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0245 is chloro trifluoromethyl ethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0246 is chloro trifluoromethyl fluoro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0247 is chloro trifluoromethyl hydrogen CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0248 is chloro trifluoromethyl methoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0249 is chloro trifluoromethyl methyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0250 is chloro trifluoromethyl nitro CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0251 is chloro trifluoromethyl trifluoromethoxy CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-Cl
  • X 3 Y 1 is CH
  • Y 2 is
  • P.0252 is chloro trifluoromethyl trifluoromethyl CH, Y 3 is CH
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is
  • X 1 is chloro
  • X 2 is C-I
  • X s is chlorodifluoromethy
  • Y 1 is CH
  • Y 2 is

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Abstract

The present invention relates to compounds of formula (IA) wherein QA is QA1 or QA2 P is P1, heterocyclyl or heterocyclyl substituted by one to five Z; and wherein A1, A2, A3, A4, G1, Z, R1, R2, R3 and R4 are as defined in claim 1; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (IA), to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising the compounds of formula (IA) and to methods of using the compounds of formula (IA) to control insect, acarine, nematode and mollusc pests.

Description

DIHYDROFURAN DERIVATIVES AS I SECTICIDAL COMPOUNDS The present invention relates to certain dihydrofuran derivatives, to processes and intermediates for preparing these derivatives, to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising these derivatives and to methods of using these derivatives to control insect, acarine, nematode and mollusc pests. In particular, the invention relates to stereoisomers of said dihydrofuran derivatives.
Certain isoxazoline derivatives with insecticidal properties are disclosed, for example, in EP 1,731,512. However there is a continuing need to find new biologically active compounds as well as new biologically active compounds displaying superior properties for use as agrochemical active ingredients, for example greater biological activity, different spectrum of activity, increased safety profile, or increased biodegradability.
It has now surprisingly been found that certain dihydrofuran derivatives have insecticidal properties.
The present invention therefore provides compounds of formula (IA)
Figure imgf000003_0001
wherein
QA is QA1 or QA2
Figure imgf000003_0002
QA1 QA2
P is PI, heterocyclyl or heterocyclyl substituted by one to five Z;
Figure imgf000003_0003
P1
A1, A2, A3 and A4 are independently of each other C-H, C-R5, or nitrogen;
G1 is oxygen or sulfur;
R1 is hydrogen, Ci-Cgalkyl, d-Cgalkoxy-, Ci-Cgalkylcarbonyl-, or Ci-Cgalkoxycarbonyl-;
R2 is Ci-Cgalkyl or Ci-Cgalkyl substituted by one to five R6, C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R7, aryl-Ci-C4alkylene- or aryl-Ci-C4alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl-Ci-C4alkylene- or heterocyclyl-Ci-C4alkylene- wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, Ci-C8alkylaminocarbonyl-Ci-C4 alkylene, Q- Cghaloalkylaminocarbonyl-Ci-C4 alkylene, C3-Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene, Ci-Cealkyl- 0-N=CH-, C C6haloalkyl-0-N=CH-,
R3 is Ci-Cghaloalkyl;
R4 is aryl or aryl substituted by one to five R9, or heteroaryl or heteroaryl substituted by one to five R9; each R5 is independently halogen, cyano, nitro, Ci-Cgalkyl, Ci-Cghaloalkyl, d-Cgalkenyl, d- Cghaloalkenyl, d-Cgalkynyl, Ci-Cghaloalkynyl, C3-Ciocycloalkyl, Ci-Cgalkoxy-, Ci-Cghaloalkoxy-, d- Cgalkylthio-, Ci-Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, or Ci-Cghaloalkylsulfonyl-;
each R6 is independently halogen, cyano, nitro, hydroxy, amino, Ci-Cgalkylamino, (Ci-Cgalkyl)2amino, Ci-Cgalkylcarbonylamino, Ci-Cghaloalkylcarbonylamino, Ci-Cgalkoxy-, Ci-Cghaloalkoxy-, aryloxy or aryloxy substituted by one to five R10, aryloxy-Ci-C4alkylene or aryloxy-Ci-C4alkylene wherein the aryl moiety is substituted by one to five R10, d-Cgalkylcarbonyl-, Ci-C8alkoxycarbonyl-, mercapto, Cr Cgalkylthio-, Ci-Cghaloalkylthio-, CpCgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, Cr Cghaloalkylsulfonyl-, aryl-Ci-C4alkylthio or aryl-Ci-C4alkylthio wherein the aryl moiety is substituted by one to five R10;
each R7 is independently halogen, CpCgalkyl, CpCgalkenyl, d-C8alkynyl,
Figure imgf000004_0001
Q- Cghaloalkyl-0-N=; Ci-Cgalkoxy, CpCgakoxycarbonyl;
each R8 is independently halogen, cyano, nitro, oxo, CpCgalkyl, Ci-Cghaloalkyl, CpCgcyanoalkyl, C2- Cgalkenyl, C2-Cghaloalkenyl, C2-Cgalkynyl, C2-Cghaloalkynyl, C3-Ciocycloalkyl, d-Ciocycloalkyl-Cr C4alkylene, hydroxy, Ci-Cgalkoxy-, Ci-Cghaloalkoxy-, mercapto, CpCgalkylthio-, Ci-Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, Ci-Cghaloalkylsulfonyl-, Cr
Cgalkylaminosulfonyl, (Ci-Cgalkyl)2aminosulfonyl-, Q-Cgalkylcarbonyl-, Ci-C8alkoxycarbonyl-, aryl or aryl substituted by one to five R10, heterocyclyl or heterocyclyl substituted by one to five R10, aryl-d- C alkylene or aryl-Ci-C alkylene wherein the aryl moiety is substituted by one to five R10, heterocyclyl- Ci-C alkylene or heterocyclyl-Ci-C alkylene wherein the heterocyclyl moiety is substituted by one to five R10, aryloxy or aryloxy substituted by one to five R10, aryloxy-Ci-C alkylene or aryloxy-Ci-C alkylene wherein the aryl moiety is substituted by one to five R10;
each R9 is independently halogen, cyano, nitro, CpCgalkyl, Ci-Cghaloalkyl, C2-Cgalkenyl, - Cghaloalkenyl, C2-Cgalkynyl, C2-Cghaloalkynyl, hydroxy, Ci-Cgalkoxy-, Ci-Cghaloalkoxy-, mercapto, d- Cgalkylthio-, Ci-Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, d- Cghaloalkylsulfonyl-, Ci-Cgalkylcarbonyl-, Ci-Cgalkoxycarbonyl-, aryl or aryl substituted by one to five R10, or heterocyclyl or heterocyclyl substituted by one to five R10;
each R10 is independently halogen, cyano, nitro, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4alkoxy-, or d- C4haloalkoxy-;
each Z is independently halogen,
Figure imgf000004_0002
substituted by one to five R6, nitro, Cp Ci2alkoxy or
Figure imgf000004_0003
substituted by one to five R6, cyano, Ci-Cgalkylsulfonyl, Ci-Cghaloalkylsulfinyl,
Figure imgf000004_0004
hydroxyl or thiol; or a salt or N-oxide thereof. The invention also provides mixtures comprising a compound of formula (IA) and a compound of formula (IB)
Figure imgf000005_0001
wherein Q is Q 1 or Q 2
Figure imgf000005_0002
QB1 QB2
wherein A1, A2, A3, A4, P, R3 and R4 are as defined for compounds of formula (IA);
and wherein the mixture is enriched for the compound of formula (IA).
The compounds of formula (IA) may exist in different geometric or optical isomers or tautomeric forms. Other than the chiral configuration at the asymmetric carbon indicated, this invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds. The invention also covers N-oxides and salts.
The compounds of the invention may contain one or more additional asymmetric carbon atoms and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such.
Alkyl groups (either alone or as part of a larger group, such as alkoxy-, alkylthio-, alkylsulfinyl-, alkylsulfonyl-, alkylcarbonyl- or alkoxycarbonyl-) can be in the form of a straight or branched chain and are, for example, methyl, ethyl, propyl, prop-2-yl, butyl, but-2-yl, 2 -methyl-prop -1-yl or 2-methyl-prop-2- yl. The alkyl groups are preferably Ci-C6, more preferably Q-C4, most preferably Q-C3 alkyl groups. Where an alkyl moiety is said to be substituted, the alkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
Alkylene groups can be in the form of a straight or branched chain and are, for example, -CH2-, -CH2-CH2-, -CH(CH3)-, -CH2-CH2-CH2-, -CH(CH3)-CH2-, or -CH(CH2CH3)-. The alkylene groups are preferably C -C3, more preferably C1-C2, most preferably Ci alkylene groups.
Alkenyl groups can be in the form of straight or branched chains, and can be, where appropriate, of either the (E)- or (Z)-configuration. Examples are vinyl and allyl. The alkenyl groups are preferably C2-C6, more preferably C2-C4, most preferably C2-C3 alkenyl groups.
Alkynyl groups can be in the form of straight or branched chains. Examples are ethynyl and propargyl. The alkynyl groups are preferably C2-C6, more preferably C2-C4, most preferably C2-C3 alkynyl groups.
Halogen is fluorine, chlorine, bromine or iodine.
Haloalkyl groups (either alone or as part of a larger group, such as haloalkoxy-, haloalkylthio-, haloalkylsulfinyl- or haloalkylsulfonyl-) are alkyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, difluoromethyl, trifluoromethyl, chlorodifluoromethyl or 2,2,2-trifluoro-ethyl.
Haloalkenyl groups are alkenyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, 2,2-difluoro-vinyl or 1 ,2-dichloro-2-fluoro-vinyl.
Haloalkynyl groups are alkynyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, l-chloro-prop-2-ynyl.
Cycloalkyl groups or carbocyclic rings can be in mono- or bi-cyclic form and are, for example, cyclopropyl, cyclobutyl, cyclohexyl and bicyclo[2.2.1]heptan-2-yl. The cycloalkyl groups are preferably C3-C8, more preferably C3-C6 cycloalkyl groups. Where a cycloalkyl moiety is said to be substituted, the cycloalkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
Aryl groups (either alone or as part of a larger group, such as aryl-alkylene-) are aromatic ring systems which can be in mono-, bi- or tricyclic form. Examples of such rings include phenyl, naphthyl, anthracenyl, indenyl or phenanthrenyl. Preferred aryl groups are phenyl and naphthyl, phenyl being most preferred. Where an aryl moiety is said to be substituted, the aryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
Heteroaryl groups (either alone or as part of a larger group, such as heteroaryl-alkylene-) are aromatic ring systems containing at least one heteroatom and consisting either of a single ring or of two or more fused rings. Preferably, single rings will contain up to three heteroatoms and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulfur. Examples of monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (e.g. 1.2.4 triazoyl), furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl. Examples of bicyclic groups include purinyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl and benzothiazolyl. Monocyclic heteroaryl groups are preferred, pyridyl being most preferred. Where a heteroaryl moiety is said to be substituted, the heteroaryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
Heterocyclyl groups or heterocyclic rings (either alone or as part of a larger group, such as heterocyclyl-alkylene-) are defined to include heteroaryl groups and in addition their unsaturated or partially unsaturated analogues. Examples of monocyclic groups include isoxazolyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, [l,3]dioxolanyl, piperidinyl, piperazinyl, [l,4]dioxanyl, and morpholinyl or their oxidised versions such as 1 -oxo-thietanyl and 1,1-dioxo-thietanyl. Examples of bicyclic groups include 2,3-dihydro-benzofuranyl, benzo[l,4]dioxolanyl, benzo[l,3]dioxolanyl, chromenyl, and 2,3- dihydro-benzo[l,4]dioxinyl. Where a heterocyclyl moiety is said to be substituted, the heterocyclyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
Preferred values of P, A1, A2, A3, A4, G1, Z, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are, in any combination, as set out below.
Preferably, P is PI, or a heterocycle selected from HI to H9
Figure imgf000007_0001
H4
Figure imgf000007_0002
H5 H6 H7 H8 H9
k is 0, 1 or 2.
Preferably no more than two of A1, A2, A3 and A4 are nitrogen, more preferably no more than one of A1, A2, A3 and A4 is nitrogen.
Preferably A1 is C-H or C-R5, most preferably A1 is C-R5.
Preferably A2 is C-H or C-R5, most preferably A2 is C-H.
Preferably A3 is C-H or C-R5, most preferably A3 is C-H.
Preferably A is C-H or C-R , most preferably A is C-H.
IInn c one preferred group of compounds A1 is C-R5, A2 is C-H, A3 is C-H or nitrogen and A4 is C-H or nitrogen.
In another preferred group of compounds A1 is C-R5, A2 is C-H, A3 is C-H and A4 is C-H.
Preferably G1 is oxygen.
Preferably R1 is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl-, more preferably hydrogen, methyl or ethyl, most preferably hydrogen.
Preferably, R2 is CpCgalkyl or CpCgalkyl substituted by one to five R6, C3-Ci0cycloalkyl or C3-
Ciocycloalkyl substituted by one to five R7, aryl-Ci-C4 alkylene- or aryl-Ci-C4alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl-Ci-C4 alkylene- or heterocyclyl-Ci-C4 alkylene - wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, Ci-C8alkylaminocarbonyl-Ci-C4 alkylene, Q- Cghaloalkylaminocarbonyl-Ci-Q alkylene, C -C8cycloalkyl-aminocarbonyl-Ci-C alkylene, or group A
Figure imgf000007_0003
wherein R11 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, cyclopropyl, cyclopropyl-methyl, cyclobutyl, cyclobutyl-methyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R12, or R11 is pyridyl-methyl- or pyridyl-methyl- substituted by one to three R12; and each R12 is independently fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, cyano or methoxy.
More preferably R2 is Ci-C8alkyl or Q-Qalkyl substituted by one to five R6, C3-Ci0cycloalkyl or C3-Ciocycloalkyl substituted by one to five R7, aryl-Ci-C4alkylene- or aryl-Ci-C4alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl-Ci-C4 alkylene- or heterocyclyl-Ci-C4alkylene- wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, d-dalkylaminocarbonyl-d-d alkylene, d- dhaloalkylaminocarbonyl-d-d alkylene, -dcycloalkyl-aminocarbonyl-d-d alkylene, or group A
Figure imgf000008_0001
wherein each aryl group is a phenyl group and each heterocyclyl group is independently selected from pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl,
tetrahydrothiophenyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl, benzothiazolyl, oxetanyl, thietanyl, oxo-thietanyl, dioxo-thietanyl, pyrrolidinyl, tetrahydrofuranyl, [l,3]dioxolanyl, piperidinyl, piperazinyl, [l,4]dioxanyl, and morpholinyl, 2,3-dihydro- benzofuranyl, benzo[l,3]dioxolanyl, and 2,3-dihydro-benzo[l,4]dioxinyl.
More preferably R2 is d-dalkyl or Ci-Cgalkyl substituted by one to five R6, C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R7, aryl-Ci-C4alkylene- or aryl-Ci-C4alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl-Ci-C4alkylene- or heterocyclyl-d-dalkylene- wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, Ci-Cgalkylaminocarbonyl-Ci-C4 alkylene, d- Cghaloalkylaminocarbonyl-Crd alkylene, C3-Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene, or group A
Figure imgf000008_0002
wherein each aryl group is a phenyl group and each heterocyclyl group is selected from 1 ,2,3 triazolyl, 1 ,2,4 triazolyl, tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, tetrahydrothiophenyl, isoxazolinyl, pyridyl, tetrahydrofuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo- thietanyl.
More preferably still R2 is d-dalkyl or d-dalkyl substituted by one to five R6, C3- docycloalkyl or d-d0cycloalkyl substituted by one to five R7, aryl-d-dalkylene- or aryl-d- C4 alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl-d-dalkylene- or heterocyclyl-d-dalkylene- wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, d- dalkylaminocarbonyl-d-d alkylene, d-dhaloalkylaminocarbonyl-d-d alkylene, d-dcycloalkyl- aminocarbonyl-d-d alkylene, or group A
Figure imgf000008_0003
(A); wherein each aryl group is a phenyl group and each heterocyclyl group is selected from pyridyl, tetrahydroiuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo- thietanyl.
More preferably still R2 is Ci-C8alkyl or Ci-C8alkyl substituted by one to five R6, C3-Ciocyclo- alkyl or C3-Ciocycloalkyl substituted by one to five R7, phenyl-Ci-C4alkylene- or phenyl-Ci-C4alkylene- wherein the phenyl moiety is substituted by one to five R8, pyridyl-Ci-C4alkylene- or pyridyl-Cr
C4alkylene- wherein the pyridyl moiety is substituted by one to four R8, tetrahydrofuranyl-Ci-C4alkylene- or tetrahydrofuranyl-Ci-C4alkylene- wherein the tetrahydrofuranyl moiety is substituted by one to five R8, imidazolyl-Ci-C4alkylene- or imidazolyl-Ci-C4alkylene- wherein the imidazolyl moiety is substituted by one to three R8, pyrazolyl-Ci-C4alkylene- or pyryazolyl-Ci-C4alkylene- wherein the pyrazolyl moiety is substituted by one to three R8, pyrrolyl-Ci-C4 alkylene- or pyrrolyl-Ci-C4alkylene- wherein the pyrrolyl moiety is substituted by one to four R8, thiazolyl-Ci-C4alkylene- or thiazolyl-Ci-C4alkylene- wherein the thiazolyl moiety is substituted by one to four R8, oxetanyl- C1-C4 alkylene or oxetanyl-Ci-C4 alkylene wherein the oxetanyl moiety is substituted by one to five R8, thietanyl-Ci-C4 alkylene or thietanyl-Ci-C4 alkylene wherein the thietanyl moiety is substituted by one to five R8, oxo-thietanyl-Ci-C4 alkylene or oxo-thietanyl-Ci-C4 alkylene wherein the oxo-thietanyl moiety is substituted by one to five R8, dioxo- thietanyl-Ci-C4 alkylene or dioxo-thietanyl-Ci-C4 alkylene wherein the dioxo-thietanyl moiety is substituted by one to five R8, oxetanyl or oxetanyl substituted by one to five R8, thietanyl or thietanyl substituted by one to five R8, oxo-thietanyl or oxo-thietanyl substituted by one to five R8, dioxo-thietanyl or dioxo-thietanyl substituted by one to five R8, Ci-C8alkylaminocarbonyl-Ci-C4 alkylene, Cp
C8haloalkylaminocarbonyl-Ci-C4 alkylene, C -C8cycloalkyl-aminocarbonyl-Ci-C4 alkylene, or group A
Figure imgf000009_0001
Even more preferably R2 is Ci-C8alkyl or Ci-C8alkyl substituted by one to five R6, C3-Ciocyclo- alkyl or C3-Ciocycloalkyl substituted by one to five R7, phenyl-Ci-C4alkylene- or phenyl-Ci-C4alkylene- wherein the phenyl moiety is substituted by one to five R8, pyridyl-Ci-C4alkylene- or pyridyl-Cr
C4alkylene- wherein the pyridyl moiety is substituted by one to four R8, oxetanyl or oxetanyl substituted by one to five R8, thietanyl-Ci-C4 alkylene or thietanyl-Ci-C4 alkylene wherein the thietanyl moiety is substituted by one to five R8, oxo-thietanyl-Ci-C4 alkylene or oxo-thietanyl-Ci-C4 alkylene wherein the oxo-thietanyl moiety is substituted by one to five R8, dioxo-thietanyl-Ci-C4 alkylene or dioxo-thietanyl- C1-C4 alkylene wherein the dioxo-thietanyl moiety is substituted by one to five R8, thietanyl or thietanyl substituted by one to five R8, oxo-thietanyl or oxo-thietanyl substituted by one to five R8, dioxo-thietanyl or dioxo-thietanyl substituted by one to five R8, Ci-C8alkylaminocarbonyl-Ci-C4 alkylene, Cr
C8haloalkylaminocarbonyl-Ci-C4 alkylene, or C3-C8cycloalkyl-aminocarbonyl-Ci-C4 alkylene, or group A
Figure imgf000010_0001
Yet even more preferably R is Q-Cgalkyl or Q-Cgalkyl substituted by one to three halogen atoms, C3-Ci0cycloalkyl or C3-Ci0cycloalkyl substituted by one or two groups independently selected from fluoro and methyl, phenyl-Ci-C4alkylene- or phenyl-Ci-C4alkylene- wherein the phenyl moiety is substituted by one to five R8, pyridyl-Ci-C4alkylene- or pyridyl-Ci-C4alkylene- wherein the pyridyl moiety is substituted by one to four R8, thietanyl, oxo-thietanyl, dioxo-thietanyl, Q- Cgalkylaminocarbonyl-methylene, Ci-Cghaloalkylaminocarbonyl-methylene, C3-Cgcycloalkyl- aminocarbonyl-methylene, or group A
Figure imgf000010_0002
A group of preferred compounds are those wherein R is Ci-C6alkyl or Ci-C6alkyl substituted by one to five R6, for example ethyl-, butyl-, but-2-yl-, 3-bromo-propyl-, 2,2,2-trifluoro-ethyl-, 3,3,3- trifluoro-propyl-, 2-methoxy-ethyl-, and l-methoxy-prop-2-yl-.
A group of preferred compounds are those wherein R2 is C3-Cgcycloalkyl or C3-C8cycloalkyl substituted by one to five R7, for example cyclobutyl-, 2-fluoro-cyclopropyl and 2-methyl-cyclohex-l -yl-.
A group of preferred compounds are those wherein R2 is aryl-Ci-C2alkylene- or aryl-Q- C2alkylene- wherein the aryl moiety is substituted by one to five R8, for example phenyl-methyl-, 1 - phenyl-eth-l-yl-, 2-phenyl-eth-l -yl-, (3-chloro-phenyl)-methyl-, (2-fluoro-phenyl)-methyl-, (4-methoxy- phenyl)-methyl-, (2-trifluoromethyl-phenyl)-methyl-, and (2-trifluoromethoxy-phenyl)-methyl-.
A group of preferred compounds are those wherein R2 is heterocyclyl-Ci-C2alkylene- or heterocyclyl-Ci-C2alkylene- wherein the heterocyclyl moiety is substituted by one to five R8, for example (pyrid-2-yl)-methyl-, (pyrid-3-yl)-methyl-, (2-chloro-pyrid-5-yl)-methyl-, (1 -methyl- lH-imidazol-4-yl)- methyl-, (furan-2-yl)-methyl-, 2-(thiophen-2'-yl)-eth-l -yl-, 2-(indol-3'-yl)-eth-l-yl-, (lH-benzimidazol-2- yl)-methyl-, (oxetan-2-yl)-methyl-, (tetrahydrofuran-2-yl)-methyl-, 2-([l',3']dioxolan-2'-yl)-eth-l -yl-, 2- (morpholin-4'-yl)-eth-l-yl-, 2-(benzo[l',3']dioxol-5'-yl)-eth-l-yl-, (2,3-dihydro-benzo[l,4]dioxin-6-yl)- methyl-, thietan-2-yl -methyl-, l -oxo-thietan-2-yl -methyl-, 1,1 -dioxo-thietan-2-yl -methyl-, thietan-3-yl- methyl-, l-oxo-thietan-3-yl-methyl-, 1,1 -dioxo-thietan-3-yl -methyl-, thietan-3-yl-ethyl-, l-oxo-thietan-3- yl-ethyl-, and l,l -dioxo-thietan-3-yl-ethyl-, preferably thietan-2-yl -methyl-, l-oxo-thietan-2-yl -methyl-, 1 ,1 -dioxo-thietan-2-yl -methyl-, thietane-3-yl -methyl-, 1 -oxo-thietan-3-yl -methyl-, 1 , 1 -dioxo-thietan-3-yl- methyl-, thietan-3-yl-ethyl-, l-oxo-thietan-3-yl-ethyl-, and l,l-dioxo-thietan-3-yl-ethyl-.
A group of preferred compounds are those wherein R2 is heterocyclyl-Ci-C2alkylene- or heterocyclyl-Ci-C2alkylene- wherein the heterocyclyl moiety is substituted by one to five R8 in which the heterocyclyl group is selected from 1,2,3 triazolyl, 1,2,4 triazolyl, tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, tetrahydrothiophenyl, isoxazolinyl, pyridyl, tetrahydrofuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo-thietanyl, preferably the heterocyclyl group is selected from thietanyl, oxo-thietanyl and dioxo-thietanyl.
A group of preferred compounds are those wherein R2 is heteroaryl-Ci-C2alkylene- or heteroaryl- Ci-C2alkylene- wherein the heteroaryl moiety is substituted by one to five R8.
A group of preferred compounds are those wherein R2 is aryl or aryl substituted by one to five R8, for example 2-chloro-phenyl-, 3-fluoro-phenyl-, 2-methyl-phenyl-, 2-chloro-6-methyl-phenyl-, 2- trifluoromethyl-phenyl-, and 2,4-dimethoxy-phenyl-.
A group of preferred compounds are those wherein R2 is heterocyclyl or heterocyclyl substituted by one to five R8, for example 3-methyl-pyrid-2-yl-, 1,3 -dimethyl- lH-pyrazol-5-yl-, 4-methyl-thiazol-2- yl-, 5-methyl-thiadiazol-2-yl-, quinolin-2-yl-, quinolin-5-yl-, benzothiazol-6-yl-, 4-methyl-benzothiazol- 2-yl-, thietan-3-yl-, l -oxo-thietan-3-yl-, l,l -dioxo-thietan-3-yl-, and 3 -methyl -thietan-3-yl-, more preferably R2 is oxetanyl, thietanyl, oxo-thietanyl or dioxo-thietanyl each optionally substituted by one to five R8, most preferably R2 is thietanyl, oxo-thietanyl or dioxo-thietanyl each optionally substituted by one to five R8. It is particularly preferred that the oxetanyl, thietanyl, oxo-thietanyl or dioxo-thietanyl ring is linked via the 3 -position.
A group of preferred compounds are those wherein R2 is heterocyclyl- or heterocyclyl substituted by one to five R8 in which the heterocyclyl group is selected from 1,2,3 triazolyl, 1,2,4 triazolyl, tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, tetrahydrothiophenyl, isoxazolinyl, pyridyl,
tetrahydrofuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo- thietanyl, preferably the heterocyclyl group is selected from thietanyl, oxo-thietanyl and dioxo-thietanyl.
A group of preferred compounds are those wherein R2 is Ci-C8alkylaminocarbonyl-Ci-C4 alkylene, Ci-Cghaloalkylaminocarbonyl-Ci-C alkylene, or C3-Cgcycloalkyl-aminocarbonyl-Ci-C alkylene, more preferably Ci-C4alkylaminocarbonyl-Ci-C4 alkylene, Ci-C4haloalkylaminocarbonyl-Ci-C4 alkylene, or C3-C6cycloalkyl-aminocarbonyl-Ci-C alkylene, most preferably CrQalkylaminocarbonyl- Ci-C2 alkylene or Ci-C haloalkylaminocarbonyl-Ci-C2 alkylene.
A group of preferred compounds are those wherein R2 is group A
Figure imgf000011_0001
Preferably R is chlorodifluoromethyl or trifluoromethyl, most preferably trifluoromethyl.
Preferably R4 is aryl or aryl substituted by one to five R9, more preferably aryl substituted by one to three R9, more preferably phenyl substituted by one to three R9, even more preferably 3,5-dibromo- phenyl-, 3,5-dichloro-phenyl-, 3,5-bis-(trifluoromethyl)-phenyl-, 3,4-dichloro-phenyl-, 3,4,5-trichloro- phenyl- 3-trifluoromethyl-phenyl-, 4-bromo-3,5-dichloro-phenyl or 3-chloro-5-trifluoromethyl-phenyl, most preferably R4 is 3,5-dichloro-phenyl.
Preferably each R5 is independently halogen, cyano, nitro, Q-Cgalkyl, Q-Cghaloalkyl, Cr C8alkenyl, Q-Cghaloalkenyl, Q-Cgalkoxy-, or Q-Cghaloalkoxy-, more preferably bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, methoxy, difluoromethoxy, or trifluoromethoxy, most preferably methyl.
Preferably each R6 is independently halogen, cyano, nitro, hydroxy, Q-Cgalkoxy-, Cp
Cghaloalkoxy-, Ci-Cgalkylcarbonyl-, Ci-Cgalkoxycarbonyl-, mercapto, Ci-Cgalkylthio-, d- Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-,
or Ci-Cghaloalkylsulfonyl-, more preferably each R6 is independently halogen, cyano, nitro, hydroxy, Cp Cgalkoxy-, Ci-Cghaloalkoxy-, mercapto, Ci-Cgalkylthio-, Ci-Cghaloalkylthio-, more preferably bromo, chloro, fluoro, methoxy, or methylthio, most preferably chloro, fluoro, or methoxy.
Preferably each R7 is independently halogen or Ci-Cgalkyl, more preferably each R7 is independently chloro, fluoro or methyl, most preferably fluoro or methyl.
Preferably each R8 is independently halogen, cyano, nitro, Q-Cgalkyl, Ci-Cghaloalkyl, Q- Cgalkenyl, C2-C8haloalkenyl, Q-Qalkynyl, Q-Qhaloalkynyl, hydroxy, Q-Qalkoxy-, Q-Cghaloalkoxy-, mercapto, Ci-Cgalkylthio-, Ci-Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Q- Cgalkylsulfonyl-, Ci-Cghaloalkylsulfonyl-, Ci-Cgalkylcarbonyl-, Ci-Cgalkoxycarbonyl-, aryl or aryl substituted by one to five R10, or heterocyclyl or heterocyclyl substituted by one to five R10, more preferably each R8 is independently halogen, cyano, nitro, Q-Qalkyl, Q-Qhaloalkyl, Q-Qalkoxy-, Q- Cghaloalkoxy-, more preferably bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy, most preferably bromo, chloro, fluoro, cyano or methyl.
Preferably each R9 is independently halogen, Q-Cgalkyl, Q-Qhaloalkyl, Q-Qalkoxy-, Q- Cghaloalkoxy-, Ci-Cgalkylthio-, or Ci-Cghaloalkylthio-, more preferably bromo, chloro, fluoro, trifluoromethyl, methoxy, or methylthio, most preferably bromo or chloro.
Preferably each R10 is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy, more preferably bromo, chloro, fluoro, nitro, or methyl, most preferably chloro, fluoro, or methyl.
Preferably R11 is methyl, ethyl or trifluoroethyl.
Preferably each Z is independently halogen, cyano, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4alkoxy, or Ci-C4haloalkoxy, more preferably each Z is independently hydrogen, halogen, methyl, halomethyl, methoxy or halomethoxy.
In one group of compounds of formula (IA)
P is PI ;
Q is Ql or Q2;
A1, A2, A3 and A4 are independently of each other C-H, C-R5, or nitrogen;
G1 is oxygen or sulfur;
R1 is hydrogen, Ci-Cgalkyl, Q-Qalkoxy-, Ci-Cgalkylcarbonyl-, or Ci-Cgalkoxycarbonyl-;
R2 is Ci-Cgalkyl or Ci-Cgalkyl substituted by one to five R6, C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R7, aryl-Ci-C4alkylene- or aryl-Ci-C4alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl-Ci-C4alkylene- or heterocyclyl-Ci-C4alkylene- wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, Ci-C8alkylaminocarbonyl-Ci-C4 alkylene, Q- Cghaloalkylaminocarbonyl-Ci-C4 alkylene, C -Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene,
Figure imgf000013_0001
RJ is Ci-Cghaloalkyl;
R4 is aryl or aryl substituted by one to five R9, or heteroaryl or heteroaryl substituted by one to five R9; each R5 is independently halogen, cyano, nitro, Q-Cgalkyl, Ci-Cghaloalkyl, Q-Cgalkenyl, Cr
Cghaloalkenyl, Q-Cgalkynyl, Ci-Cghaloalkynyl, C3-Ci0cycloalkyl, Q-Cgalkoxy-, CpCghaloalkoxy-, Q- Cgalkylthio-, Ci-Cghaloalkylthio-, CpCgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, or Ci-Cghaloalkylsulfonyl-;
each R6 is independently halogen, cyano, nitro, hydroxy, Ci-Cgalkoxy-, Ci-Cghaloalkoxy-, d-
Cgalkylcarbonyl-, Ci-Cgalkoxycarbonyl-, mercapto, CpCgalkylthio-, Ci-Cghaloalkylthio-, Cp
Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-,
or Ci-Cghaloalkylsulfonyl-;
each R7 is independently halogen or d-Cgalkyl;
each R8 and R9 is independently halogen, cyano, nitro, CpCgalkyl, Ci-Cghaloalkyl, C2-Cgalkenyl, C2- Cghaloalkenyl, C2-Cgalkynyl, C2-Cghaloalkynyl, hydroxy, Q-Cgalkoxy-, Ci-Cghaloalkoxy-, mercapto, Cp Cgalkylthio-, Ci-Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, Q- Cghaloalkylsulfonyl-, Ci-Cgalkylcarbonyl-, Ci-Cgalkoxycarbonyl-, aryl or aryl substituted by one to five R10, or heterocyclyl or heterocyclyl substituted by one to five R10;
each R10 is independently halogen, cyano, nitro, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4alkoxy-, or Q- C4haloalkoxy-;
R11 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, cyclopropyl, cyclopropyl-methyl, cyclobutyl, cyclobutyl-methyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R12, or R11 is pyridyl-methyl- or pyridyl -methyl- substituted by one to three R12;
each R12 is independently fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, cyano or methoxy; or a salt or N-oxide thereof.
A group of preferred compounds are those wherein
A1 is C-R5, A2 is C-H, A3 is C-H or nitrogen and A4 is C-H or nitrogen;
G1 is oxygen;
R1 is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl-;
R2 is CpCgalkyl or Q-Cgalkyl substituted by one to five R6, C3-Ci0cycloalkyl or C3-Ci0cycloalkyl substituted by one to five R7, aryl-Ci-C4alkylene- or aryl-Ci-C4 alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl-Ci-C4alkylene- or heterocyclyl-Ci-C4alkylene- wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, Ci-C8alkylaminocarbonyl-Ci-C4 alkylene, Q- Cghaloalkylaminocarbonyl-Ci-C4 alkylene, C -C8cycloalkyl-aminocarbonyl-Ci-C4 alkylene,
Figure imgf000014_0001
wherein each aryl group is a phenyl group and each heterocyclyl group is selected from pyridyl, tetrahydrofuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo- thietanyl;
R3 is Ci-C8 haloalkyl;
R4 is phenyl substituted by one to three R9;
R5 is independently halogen, cyano, nitro, Q-Cgalkyl, Ci-Cghaloalkyl, Q-Cgalkenyl, Ci-Cghalo- alkenyl, Q-Cgalkoxy-, or Ci-Cghaloalkoxy-;
each R6 is independently halogen, cyano, nitro, hydroxy, CpCgalkoxy-, Ci-Cghaloalkoxy-, mercapto, Ci-Cgalkylthio-, Ci-Cghaloalkylthio-;
each R7 is independently chloro, fluoro or methyl;
each R8 is independently halogen, cyano, nitro, CpCgalkyl, Ci-Cghaloalkyl, d-Cgalkoxy-, d- Cghaloalkoxy-;
each R9 is independently halogen, CpCgalkyl, Ci-Cghaloalkyl, Q-Cgalkoxy-, Ci-Cghaloalkoxy-, Ci-Cgalkylthio-, or Ci-Cghaloalkylthio-;
Another group of preferred compounds are those wherein
A1 is C-R5, A2 is C-H, A3 is C-H and A4 is C-H;
G1 is oxygen;
R is hydrogen, methyl or ethyl;
R2 is Ci-Cgalkyl or d-Cgalkyl substituted by one to five R6, C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R7, phenyl-Ci-C4alkylene- or phenyl-Ci-C4alkylene- wherein the phenyl moiety is substituted by one to five R8, pyridyl-Ci-C4alkylene- or pyridyl-Ci-C4alkylene- wherein the pyridyl moiety is substituted by one to four R8, oxetanyl or oxetanyl substituted by one to five R8, thietanyl-Ci-C4 alkylene or thietanyl-Ci-C4 alkylene wherein the thietanyl moiety is substituted by one to five R8, oxo- thietanyl-Ci-C4 alkylene or oxo-thietanyl-Ci-C4 alkylene wherein the oxo-thietanyl moiety is substituted by one to five R8, dioxo-thietanyl-Ci-C4 alkylene or dioxo-thietanyl-Ci-C4 alkylene wherein the dioxo- thietanyl moiety is substituted by one to five R8, thietanyl or thietanyl substituted by one to five R8, oxo- thietanyl or oxo-thietanyl substituted by one to five R8, dioxo-thietanyl or dioxo-thietanyl substituted by one to five R8, Ci-Cgalkylaminocarbonyl-Ci-C4 alkylene, Ci-Cghaloalkylaminocarbonyl-Ci-C4 alkylene, C3-Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene or group A
Figure imgf000014_0002
(A); R3 is chlorodifluoromethyl or trifluoromethyl;
R4 is 3,5-dibromo-phenyl-, 3,5-dichloro-phenyl-, 3,5-bis-(trifluoromethyl)-phenyl-, 3,4-dichloro- phenyl-, 3,4,5-trichloro-phenyl-, 3-trifluoromethyl-phenyl-, 4-bromo-3,5-dichloro-phenyl or 3-chloro-5- trifluoromethyl-phenyl;
R5 is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, methoxy, difluoromethoxy, or trifluoromethoxy;
each R6 is independently bromo, chloro, fluoro, methoxy, or methylthio;
each R7 is independently fluoro or methyl;
each R8 is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy;
R11 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, cyclopropyl, cyclopropyl-methyl, cyclobutyl, cyclobutyl-methyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R12, or R11 is pyridyl-methyl- or pyridyl-methyl- substituted by one to three R12;
each R12 is independently fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, cyano or methoxy.
A further group of preferred compounds are those wherein
P is PI ;
A1 is C-R5, A2 is C-H, A3 is C-H and A4 is C-H;
G1 is oxygen;
R1 is hydrogen;
R2 is Ci-C8alkyl or Q-Cgalkyl substituted by one to three halogen atoms, C3-Ci0cycloalkyl or C3- Ciocycloalkyl substituted by one or two groups independently selected from fluoro and methyl, phenyl- Ci-C4alkylene- or phenyl-Ci-C4alkylene- wherein the phenyl moiety is substituted by one to five R8, pyridyl-Ci-C4 alkylene- or pyridyl-Ci-C4 alkylene- wherein the pyridyl moiety is substituted by one to four R8, thietanyl, oxo-thietanyl, dioxo-thietanyl, Ci-C alkylaminocarbonyl-Ci-C alkylene, Q- C haloalkylaminocarbonyl-Ci-C alkylene, C3-C cycloalkyl-aminocarbonyl-Ci-C alkylene, or group A
Figure imgf000015_0001
R is trifluoromethyl;
R4 is 3,5-dichloro-phenyl;
R5 is methyl;
each R8 is independently bromo, chloro, fluoro, cyano or methyl;
R11 is methyl, ethyl or trifluoroethyl.
A further group of preferred compounds are those wherein
P is PI ; A1 is C-R5, A2 is CH, A3 is CH and A4 is CH;
G1 is oxygen;
R1 is hydrogen;
R2 is C2-C6alkyl or C2-Cealkyl substituted by one to three halogen atoms, C3-Cgcycloalkyl or C3- Cgcycloalkyl substituted by one or two groups independently selected from fluoro and methyl, phenyl-d- C2alkylene- or phenyl-C i-C2alkylene- wherein the phenyl moiety is substituted by one to five R8, pyridyl- Ci-C2alkylene- or pyridyl-Ci-C2alkylene- wherein the pyridyl moiety is substituted by one to four R8, thietanyl, oxo-thietanyl, dioxo-thietanyl, Ci-C4alkylaminocarbonyl-Ci-C2 alkylene or Q- C4haloalkylaminocarbonyl-Ci-C2 alkylene, or group A
Figure imgf000016_0001
(A);
R is trifluoromethyl;
R4 is 3,5-dichloro-phenyl;
R5 is methyl;
each R8 is independently bromo, chloro, fluoro, cyano or methyl;
R11 is methyl, ethyl or trifluoroethyl.
In a further group of compounds of formula (IA) P is PI, Q is QA1 or QA2. The preferered substituent definitions given above also apply to the substituents in the preferred groups of compounds of formula (IA) above in those cases where a preferred substituent definition is narrower.
In one embodiment the present invention provides compounds of formula (IAa)
Figure imgf000016_0002
wherein G1, R1, R2, R3, R4 and R5 are as defined for compounds of formula (IA); or a salt or N-oxide thereof. The preferences for G1, R1, R2, R3, R4 and R5 are the same as the preferences set out for the corresponding substituents of compounds of the formula (IA).
In a further embodiment the present invention provides a mixture comprising a compound of formula (IAa) as defined above and a compound of formula (IBa)
(IBa)
Figure imgf000016_0003
wherein G1, R1, R2, R3, R4 and R5 and pereferences thereof are as defined for compounds of formula (IA); and wherein the mixture is enriched for compounds of formula (IAa).
In a further embodiment the present invention provides compounds of formula (IAb)
Figure imgf000017_0001
wherein G1, R1, R2, R3, R4 and R5 are as defined for compounds of formula (IA); or a salt or N-oxide thereof. The preferences for G1, R1, R2, R3, R4 and R5 are the same as the preferences set out for the corresponding substituents of compounds of the formula (IA).
In a further embodiment the present invention provides a mixture comprising a compound of formula (IAb) as defined above and a compound of formula (IBb)
Figure imgf000017_0002
wherein G1, R1, R2, R3, R4 and R5 and preferences thereof are as defined for compounds of formula (IA); and wherein the mixture is enriched for compounds of formula (IAb).
In a further embodiment the present invention provides compounds of formula (IAc)
Figure imgf000017_0003
wherein R3, R4 and R5 are as defined for compounds of formula (IA) and Het is selected from HI to H9 as defined for compounds of formula (IA); or a salt or N-oxide thereof. The preferences for R3, R4, R5, and Het are the same as the preferences set out for the corresponding substituents of compounds of the formula (IA).
In a further embodiment the present invention provides a mixture comprising a compound of formula (IAc) as defined above and a compound of formula (IBc)
Figure imgf000017_0004
wherein R3, R4 and R5 are as defined for compounds of formula (IA) and Het is selected from HI to H9 as defined for compounds of formula (IA) and wherein the mixture is enriched for compounds of formula (IAc). The preferences for R3, R4, R5, and Het are the same as the preferences set out for the
corresponding substituents of compounds of the formula (IA).
In a further embodiment the present invention provides compounds of formula (IAd)
Figure imgf000018_0001
wherein R3, R4 and R5 are as defined for compounds of formula (IA) and Het is selected from HI to H9 as defined for compounds of formula I; or a salt or N-oxide thereof. The preferences for R3, R4, R5, and Het are the same as the preferences set out for the corresponding substituents of compounds of the formula (IA).
In a further embodiment the present invention provides a mixture comprising a compound of formula (IAd) as de rmula (IBd)
Figure imgf000018_0002
wherein R3, R4 and R5 and preferences thereof are as defined for compounds of formula (IA) and Het is selected from HI to H9 as defined for compounds of formula (IA) and wherein the mixture is enriched for compounds of formula (IAd).
Certain intermediates are novel and as such form further aspects of the invention. One group of novel intermediates are compo
Figure imgf000018_0003
wherein QA, A1, A2, A3, and A4 are as defined for a compound of formula (IA), G1 is oxygen, and R is hydroxy, Ci-Ci5alkoxy or halogen, such as bromo, chloro or fluoro; or a salt or N-oxide thereof. The preferences for QA, A1, A2, A3, and A4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA). Preferably R is hydroxy, Q-Cealkoxy or chloro.
The invention also provides a mixture comprising a compound of formula (IIA) as defined above and a compound of formula (IIB)
Figure imgf000019_0001
wherein A1, A2, A3, and A4 and preferences thereof are as defined for a compound of formula (IA), QB is as defined for a compound of formula (IB), G1 is oxygen, and R is hydroxy, Ci-Ci5alkoxy (e.g. Cr C6alkoxy) or halogen, such as bromo, chloro or fluoro, preferably hydroxy, Ci-C6alkoxy or chloro, and wherein the mixture is enriched for compounds of formula (IIA).
One group of compounds of formula (IIA) are compounds of formula (IIAa)
Figure imgf000019_0002
wherein A1, A2, A3, A4, R3 and R4 are as defined for a compound of formula (IA), G1 is oxygen, and R is hydroxy, CpCealkoxy or halogen, such as bromo, chloro or fluoro; or a salt or N-oxide thereof. The preferences for A1, A2, A3, A4, R3 and R4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA). Preferably R is hydroxy, CpCealkoxy or chloro.
The invention also provides a mixture comprising a compound of formula (IIAa) as defined above and a compound of formula (IIBa)
Figure imgf000019_0003
wherein A1, A2, A3, A4, R3 and R4 and preferences thereof are as defined for a compound of formula (IA), G1 is oxygen, and R is hydroxy, CpCealkoxy or halogen, such as bromo, chloro or fluoro, and wherein the mixture is enriched for compounds of formula (IIAa).
A further group of compounds of formula IIA are compounds of formula (IIAb)
(I IAb)
Figure imgf000019_0004
wherein A1, A2, A3, A4, R3 and R4 are as defined for a compound of formula (IA), G1 is oxygen, and R is hydroxy, CpCealkoxy or halogen, such as bromo, chloro or fluoro; or a salt or N-oxide thereof. The preferences for A1, A2, A3, A4, R3 and R4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA). Preferably R is hydroxy, CpCealkoxy or chloro.
The invention also provides a mixture comprising a compound of formula (IIAb) as defined above and a compound
Figure imgf000020_0001
wherein A1, A2, A3, A4, R3 and R4 and preferences thereof are as defined for a compound of formula (IA), G1 is oxygen, and R is hydroxy, CpCealkoxy or halogen, such as bromo, chloro or fluoro, and wherein the mixture is enriched for compounds of formula (IIAb).
A further group of compounds of formula (IIA) are compounds of formula (IIAc)
Figure imgf000020_0002
wherein A1, A2, A3, A4, R3 and R4 are as defined for a compound of formula (IA), G1 is oxygen, and R hydroxy, CpCealkoxy or halogen, such as bromo, chloro or fluoro; or a salt or N-oxide thereof. The preferences for A1, A2, A3, A4, R3 and R4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA). Preferably R is hydroxy, CpCealkoxy or chloro.
The invention also provides a mixture comprising a compound of formula (IIAc) as defined above and a compound of formula (IIBc)
Figure imgf000020_0003
wherein A1, A2, A3, A4, R3 and R4 and preferences thereof are as defined for a compound of formula (IA), G1 is oxygen, and R is hydroxy, Ci-C6alkoxy or halogen, such as bromo, chloro or fluoro, and wherein the mixture is enriched for compounds of formula (IIAc). Preferably R is hydroxy, Ci-C6alkoxy or chloro.
A further group of novel intermediates are compounds of formula (ΙΠΑ)
Figure imgf000021_0001
wherein QA, A1, A2, A3, and A4 are as defined for a compound of formula (IA), and X is a leaving group such as halogen, CpCgalkoxy, Ci-Cgalkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, Ci-Cgarylsulfonyloxy, optionally substituted Ci-Cgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g. XB is -N2 + CI", -N2 + BF4 ", -N2 + Br", -N2 + PF6 "), phosphonate esters (e.g. -OP(0)(OR)¾ wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride; or a salt or N-oxide thereof. The preferences for QA, A1, A2, A3, and A4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides a mixture comprising a compound of formula (ΙΠΑ) as defined above and a compound of formula (IIIB)
Figure imgf000021_0002
wherein A1, A2, A3, and A4 and preferences thereof are as defined for a compound of formula (IA), QB is as defined for compounds of formula (IB) and XB is a leaving group such as halogen, CpCgalkoxy, Cr Cgalkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, Ci-Cgarylsulfonyloxy, optionally substituted Cp Cgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g. XB is -N2 + CI", -N2 + BF4 ", -N2 + Br", - N2 + PF6 "), phosphonate esters (e.g. -OP(0)(OR)2; wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride, and wherein the mixture is enriched for compounds of formula (IIIA).
One group of c compounds of formula (IIIAa)
(IIIAa)
Figure imgf000021_0003
wherein A1, A2, A3, A4, R3 and R4 are as defined for a compound of formula (IA), and X is as defined for compounds of formula (IIIA). The preferences for A1, A2, A3, A4, R3 and R4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides a mixture comprising a compound of formula (IIIAa) as defined above and a compound
(IIIBa)
Figure imgf000021_0004
wherein A1, A2, A3, A4, R3 and R4 and preferences thereof are as defined for a compound of formula (IA), and XB is as defined for compounds of formula (IIIA), and wherein the mixture is enriched for compounds of formula (IIIAa).
A further group are compounds of formula (IIIAb)
(IIIAb)
Figure imgf000022_0001
wherein A1, A2, A3, A4, R3 and R4 are as defined for a compound of formula (IA), and X is as defined for compounds of formula (IIIA). The preferences for A1, A2, A3, A4, R3 and R4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides a mixture comprising a compound of formula (IIIAb) as defined above and a compound
(IIIBb)
Figure imgf000022_0002
wherein A1, A2, A3, A4, R3 and R4 and preferences thereof are as defined for a compound of formula (IA), and XB is as defined for compounds of formula (IIIA), and wherein the mixture is enriched for compounds of formula (IIIAb).
A further group of compounds of formula (IIIA) are compounds of formula (IIIAc)
(IIIAc)
Figure imgf000022_0003
wherein A1, A2, A3, A4, R3 and R4 are as defined for a compound of formula (IA) and X is as defined for compounds of formula (IIIA). The preferences for A1, A2, A3, A4, R3 and R4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides a mixture comprising a compound of formula (IIIAc) as defined above and a compound of formula (IIIBc)
(IIIBc)
Figure imgf000022_0004
wherein A1, A2, A3, A4, R3 and R4 and pereferences thereof are as defined for a compound of formula (IA) and XB is as defined for compounds of formula (IIIA), and wherein the mixture is enriched for compounds of formula (IIIAb).
A further group of nov
Figure imgf000023_0001
wherein A1, A2, A3, A4, R3 and R4 are as defined for compounds of formula (IA), Px is P as defined above (for the compound of formula (IA)), a leaving group XB, such as halogen, d-Cgalkoxy, Cp
Cgalkylsulfonyloxy, Q-Cghaloalkylsulfonyloxy, Q-Cgarylsulfonyloxy, optionally substituted Cr C8arylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g. XB is -N2 + CI", -N2 + BF4 ", -N2 + Br", - N2 + PF6 "), phosphonate esters (e.g. -OP(0)(OR)2; wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, or a salt or N-oxide thereof. The preferences for A1, A2, A3, A4, R3, R4 and preferences at position Px when Px is P are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides a mixture comprising a compound of formula (XXVA) as defined above and a compound of formula (XXVB)
Figure imgf000023_0002
wherein A1, A2, A3, A4, R3 and R4 and preferences thereof are as defined for compounds of formula (IA), Px is P as defined above, a leaving group XB, such as halogen, Q-Cgalkoxy, CpCgalkylsulfonyloxy, Cr Cghaloalkylsulfonyloxy, Ci-C8arylsulfonyloxy, optionally substituted Q-Cgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g. XB is -N2 + CI", -N2 + BF4 ", -N2 + Br", -N2 + PF6 "), phosphonate esters (e.g. -OP(0)(OR)2; wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, and wherein the mixture is enriched for compounds of formula (XXVA).
One group of compoun ds of (XXVAa)
(XXVAa)
Figure imgf000023_0003
wherein A1, A2, A3, A4, R3 and R4 are as defined for compounds of formula (IA), and X is as defined for the compound of formula (XXVA). The preferences for A1, A2, A3, A4, R3, and R4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA). The invention also provides a mixture comprising a compound of formula (XXVAa) as defined above and a compound of formula (XXVBa)
(XXVBa)
Figure imgf000024_0001
wherein A1, A2, A3, A4, R3 and R4 and preferences thereof are as defined for compounds of formula (IA), and XB is as defined for the compound of formula (XXVAa), and wherein the mixture is enriched for compounds of formula (XXVAa).
Another group compounds of formula (XXVAb)
(XXVAb)
Figure imgf000024_0002
wherein A1, A2, A3, A4, R1, R2, R3 and R4 are as defined for compounds of formula (IA). The preferences for A1, A2, A3, A4, R1, R2, R3, and R4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides a mixture comprising a compound of formula (XXVAb) as defined above and a comp
(XXVBb)
Figure imgf000024_0003
wherein A1, A2, A3, A4, R1, R2, R3 and R4 and preferences thereof are as defined for compounds of formula (IA), and XB is as defined for the compound of formula (XXVa), and wherein the mixture is enriched for compounds of formula (XXVAb).
Another group of com are compounds of formula (XXVAc)
(XXVAc)
Figure imgf000024_0004
wherein A1, A2, A3, A4, R3 and R4 are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula I. The preferences for A1, A2, A3, A4, R3, R4 and heterocyclyl are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides a mixture comprising a compound of formula (XXVAc) as defined above and a compound of formula (XXVBc) (XXVBc)
Figure imgf000025_0001
wherein A1, A2, A3, A4, R3 and R4 and preferences thereof are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula (IA), and wherein the mixture is enriched for compounds of formula (XXVAc).
Another group of novel intermediates are compounds of formula (XXIIIA)
Figure imgf000025_0002
wherein R and R are as defined for the compounds of formula (IA), or a salt or N-oxide thereof. The preferences for R3 and R4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
A preferred group of compounds of formula (XXIIIA) are those wherein R3 is CF3 and R4 is phenyl substituted by 1 to 5 R9.
The invention also provides a mixture comprising a compound of formula (XXIIIA) as defined above and a compound of formula (XXIIIB)
Figure imgf000025_0003
wherein R3 and R4 and preferences thereof are as defined for the compounds of formula (IA), e.g. R3 is CF3 and R4 is phenyl substituted by 1 to 5 R9, and wherein the mixture is enriched for compounds of formula (XXIIIA).
Another group of novel intermediates are compounds of formula (XXVIA)
R4 / Λ (XXVIA) wherein R3 and R4 adn preferences thereof are as defined for compounds of formula I, and X is a tin derivative, e.g. SnR13 3 wherein each R13 is independently Ci-Ce alkyl, a boron derivative, e.g. BF3, B(OH)2 or B(OR)2, wherein each R is independnetly Ci-C6-alkyl, Ci-C6-cycloalkyl or optionally substituted Ci-C6-cycloalkyl, e.g. optionally substituted by halogen, C1-C4 alkyl or
Figure imgf000025_0004
a leaving group, such as halogen, d-Cgalkoxy, Ci-Cgalkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, Cp Cgarylsulfonyloxy, optionally substituted Ci-Cgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g. is -N2 + CI", -N2 + BF4 ", -N2 + Br", -N2 + PF6 _), phosphonate esters (e.g. -OP(0)(OR)¾ wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride, or C(0)R wherein R is halogen, OH or
Figure imgf000025_0005
or a salt or N-oxide thereof. A preferred group of compounds of formula (XXVIA) are those wherein R3 is CF3 and R4 is phenyl substituted by 1 to 5 R9.
The invention also provides a mixture comprising a compound of formula (XXVIA) as defined above and a compound of formula (XXVIB)
Figure imgf000026_0001
wherein R and R and preferences thereof are as defined for compounds of formula (IA), e.g. R is CF3 and R4 is phenyl substituted by 1 to 5 R9, and X is a tin derivative, e.g. SnR13 3 wherein each R13 is independently Ci-C6 alkyl, a boron derivative, e.g. BF3, B(OH)2 or B(OR)2, wherein each R is independnetly Ci-C6-alkyl, Ci-C6-cycloalkyl or optionally substituted Ci-C6-cycloalkyl, e.g. optionally substituted by halogen, Q-C4 alkyl or Ci-C4haloalkyl, a leaving group, such as halogen, Q-Cgalkoxy, Q- Cgalkylsulfonyloxy, Q-Cghaloalkylsulfonyloxy, Ci-C8arylsulfonyloxy, optionally substituted Cr Cgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g. -N2 + CI", -N2 + BF4 ", -N2 + Br", -N2 + PF6 " phosphonate esters (e.g. -OP(0)(OR)¾ wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride, or C(0)R wherein R is halogen, OH or Cr Ci5alkoxy and wherein the mixture is enriched for compounds of formula (XXVIA).
Another group of novel intermediates are compounds of formula (XXVIA')
Figure imgf000026_0002
wherein R and R and preferences thereof are as defined for compounds of formula (IA), e.g. R is CF3 and R4 is phenyl substituted by 1 to 5 R9, and X is CI, Br or I, or a salt or N-oxide thereof. (Compounds of formula XXVIA' are a preferred group of compounds of formula XXVIA.)
The invention also provides a mixture comprising a compound of formula (XXVIA') as defined above and a compound of formula (XXVIB')
(XXVIB')
Figure imgf000026_0003
wherein R and R and preferences thereof are as defined for compounds of formula (IA), e.g. R is CF3 and R4 is phenyl substituted by 1 to 5 R9, and X is CI, Br or I, and wherein the mixture is enriched for compounds of formula (XXVIA').
Another group of novel intermediates are compounds of formula (XXVIIA) (xxvilA)
Figure imgf000026_0004
wherein R3 and R4 and preferences thereof are as defined for compounds of formula (IA), and X is as defined for compounds of formula (XXVIA), or a salt or N-oxide thereof. A preferred group of compounds of formula (XXVIIA) are those wherein R3 is CF3 and R4 is phenyl substituted by 1 to 5 R9.
The invention also provides a mixture comprising a compound of formula (XXVIIA) as defined above and a compound of formula (XXVIIB)
Figure imgf000027_0001
wherein R and R and preferences thereof are as defined for compounds of formula I, e.g. R is CF3 and R4 is phenyl substituted by 1 to 5 R9, and X is as defined for compounds of formula (XXVIA), and wherein the mixture is enriched for compounds of formula (XXVIIA).
Another group of novel intermediates are compounds of formula (XXVIIA')
(XXVIIA1)
Figure imgf000027_0002
wherein R3 and R4 and preferences thereof are as defined for compounds of formula (IA), and X is CI, Br or I, or a salt or N-oxide thereof. A preferred group of compounds of formula (XXVIIA') are those wherein R3 is CF3 and R4 is phenyl substituted by 1 to 5 R9. (Compounds of formula XXVIIA' are a preferred group of compounds of formula XXVIA.)
The invention also provides a mixture comprising a compound of formula (XXVIIA') as defined above and a compound of formula (XXVIIB')
(XXVIIB')
Figure imgf000027_0003
wherein R3 and R4 and preferences thereof are as defined for compounds of formula (IA), e.g. R3 is CF3 and R4 is phenyl substituted by 1 to 5 R9, and X is CI, Br or I, and wherein the mixture is enriched for compounds of formula (XXVIIA').
Another group of novel mpounds of formula (XXXVIA) (XXXVIA)
Figure imgf000027_0004
wherein R and R and preferences thereof are as defined for compounds of formula (IA), or a salt or N- oxide thereof. A preferred group of compounds of formula (XXXVIA) are those wherein R3 is CF3 and R4 is phenyl substituted by 1 to 5 R9.
The invention also provides a mixture comprising a compound of formula (XXXVIA) as defined above and a compound of formula (XXXVIB) (XXXVI B)
Figure imgf000028_0001
wherein R and R and preferences thereof are as defined for compounds of formula (IA), e.g. R is CF3 and R4 is phenyl substituted by 1 to 5 R9, and wherein the mixture is enriched for compounds of formula (XXXVIA).
Another group of novel intermediates are compounds of formula (XXXVIIA) (XXXVIIA)
Figure imgf000028_0002
wherein R3 and R4 and preferences thereof are as defined for compounds of formula (IA), or a salt or N- oxide thereof. A preferred group of compounds of formula (XXXVIIA) are those wherein R3 is CF3 and R4 is phenyl substituted by 1 to 5 R9.
The invention also provides a mixture comprising a compound of formula (XXXVIIA) as defined above and a compound of formula (XXXVIIB)
(XXXVIIB)
Figure imgf000028_0003
wherein R3 and R4 and preferences thereof are as defined for compounds of formula (IA), e.g. R3 is CF3 and R4 is phenyl substituted by 1 to 5 R9, and wherein the mixture is enriched for compounds of formula (XXXVIIA).
Another group of novel intermediates are com ounds of formula (XXXVIIIA)
Figure imgf000028_0004
(XXXVIIIA) wherein R3 and R4 and preferences thereof are as defined for compounds of formula (IA), and X is as defined for compounds of formula (XXVIA), or a salt or N-oxide thereof. A preferred group of compounds of formula (XXXVIIIA) are those wherein R3 is CF3 and R4 is phenyl substituted by 1 to 5 R9.
The invention also provides a mixture comprising a compound of formula (XXXVIIIA) as defined above and a compound of formula (XXXVIIIB)
(XXXVIIIB)
Figure imgf000028_0005
wherein R3 and R4 and preferences thereof are as defined for compounds of formula (IA), e.g. R3 is CF3 and R4 is phenyl substituted by 1 to 5 R9, and X is as defined for compounds of formula (XXVIA), wherein the mixture is enriched for compounds of formula (XXXVIIIA).
Another group o
Figure imgf000029_0001
wherein R3, R4 , A1, A2, A3, A4 and P are as defined for compounds of formula (IA), or a salt or N-oxide thereof. The preferences for R3, R4 , A1, A2, A3, A4 and P are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides a mixture comprising a compound of formula (LA) as defined above and a compound of fo
Figure imgf000029_0002
wherein R3, R4 , A1, A2, A3, A4 and P and preferences thereof are as defined for compounds of formula (IA), and wherein the mixture is enriched for compounds of formula (LA).
Another group of novel intermediates are compounds of formula (LXA)
Figure imgf000029_0003
(LXA)
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) and Px is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 and Px (when Px is P) are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
The invention also provides a mixture comprising a compound of formula (LXA) as defined above and a compound of formula (LXB)
Figure imgf000030_0001
(LXB)
wherein R3, R4 , A1, A2, A3, A4 and preferences thereof are as defined for the compound of formula (IA) and Px is as defined for the compound of formula (XXVA), and wherein the mixture is enriched for compounds of formula (LXA).
The compound of formula (LXA) includes compounds of formula (LXA') which can exist in quilibrium with compounds of formula (LXA)
Figure imgf000030_0002
(LXA')
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) and Px is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 and Px (when Px is P) are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
One group of compounds of formula (LXA) are compounds of (LXAa)
Figure imgf000030_0003
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) and XB is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
The invention also provides a mixture comprising a compound of formula (LXAa) as defined above and a compound of formula (LXBa)
Figure imgf000031_0001
wherein R3, R4 , A1, A2, A3, A4 and preferences thereof are as defined for the compound of formula (IA) and XB is as defined for the compound of formula (XXVA), and wherein the mixture is enriched for compounds of formula (LXAa).
Another group of compounds of formula (LXA) are compounds of (LXAb)
Figure imgf000031_0002
wherein R1, R2, R3, R4 , A1, A2, A3 and A4 are as defined for the compound of formula (IA), or a salt or N-oxide thereof. The preferences for R1, R2, R3, R4, A1, A2, A3, A4 are the same as the preferences set our for the corresponding substituents of the compound of formula (IA) .
The invention also provides a mixture comprising a compound of formula (LXAb) as defined above and a compound of formula (LXBb)
Figure imgf000031_0003
wherein R1, R2, R3, R4 , A1, A2, A3, A4 and preferences thereof are as defined for the compound of formula (IA), and wherein the mixture is enriched for compounds of formula (LXAb).
Another group of compounds of formula (LXA) are compounds of (LXAc)
Figure imgf000032_0001
(LXAc)
wherein A1, A2, A3, A4, R3 and R4 are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula I. The preferences for A1, A2, A3, A4, R3, R4 and heterocyclyl are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides a mixture comprising a compound of formula (LXAc) as defined above and a compound of formula (LXBc)
Figure imgf000032_0002
(LXBc)
wherein A1, A2, A3, A4, R3 and R4 and preferences thereof are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula (IA), and wherein the mixture is enriched for compounds of formula (LXAc).
Another group of novel intermediates are compounds of formula (LIXA)
Figure imgf000032_0003
(LIXA)
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) and Px is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 and Px (when Px is P) are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
The invention also provides a mixture comprising a compound of formula (LIXA) as defined above and a compound of formula (LIXB)
Figure imgf000033_0001
(LIXB)
wherein R3, R4 , A1, A2, A3, A4 and preferences thereof are as defined for the compound of formula (IA) and Px is as defined for the compound of formula (XXVA), and wherein the mixture is enriched for compounds of formula (LIXA).
One group of compounds of formula (LIXA) are compounds of (LIXAa)
Figure imgf000033_0002
(LIXAa)
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) and XB is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
The invention also provides a mixture comprising a compound of formula (LIXAa) as defined above and a compound of formula (LIXBa)
Figure imgf000033_0003
(LIXBa)
wherein R3, R4 , A1, A2, A3, A4 and preferences thereof are as defined for the compound of formula (IA) and XB is as defined for the compound of formula (XXVA), and wherein the mixture is enriched for compounds of formula (LIXAa).
Another group of compounds of formula (LIXA) are compounds of (LIXAb)
Figure imgf000033_0004
(LIXAb)
wherein R1, R2, R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA), or a salt or N- oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA). ^
The invention also provides a mixture comprising a compound of formula (LIXAb) as defined above and a compound of formula (LIXBb)
Figure imgf000034_0001
(LIXBb)
wherein R1, R2, R3, R4 , A1, A2, A3, A4 and preferences thereof are as defined for the compound of formula (IA), and wherein the mixture is enriched for compounds of formula (LIXAb).
Another group of compounds of formula (LIXA) are compounds of (LIXAc)
Figure imgf000034_0002
(LIXAc)
wherein A1, A2, A3, A4, R3 and R4 are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula I. The preferences for A1, A2, A3, A4, R3, R4 and heterocyclyl are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides a mixture comprising a compound of formula (LIXAc) as defined above and a compound of formula (LIXBc)
Figure imgf000034_0003
(LIXBc)
wherein A1, A2, A3, A4, R3 and R4 and preferences thereof are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula (IA), and wherein the mixture is enriched for compounds of formula (LIXAc).
Another group of novel intermediates are compounds of formula (LIIA)
Figure imgf000034_0004
(LIIA) wherein R and R are as defined for compounds of formula (IA), or a salt or N-oxide thereof. The preferences for R3 and R4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides a mixture comprising a compound of formula (LIIA) as defined above and a compound of formula (LIIB)
Figure imgf000035_0001
wherein R3 and R4 and preferences thereof are as defined for compounds of formula (IA), and wherein the mixture is enriched for compounds of formula (LIIA).
The compound of formula (LIIA) includes compounds of formula (LIIA') which can exist in quilibrium with compounds of formula (LIIA)
Figure imgf000035_0002
wherein R3 and R4 are as defined for compounds of formula (IA), or a salt or N-oxide thereof. The preferences for R3 and R4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
Another group of novel intermediates are compounds of formula (LIIIA)
Figure imgf000035_0003
(LIIIA)
wherein R3 and R4 are as defined for compounds of formula (IA), and each X independently represents CI, Br or I, or a salt or N-oxide thereof. The preferences for R3 and R4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides a mixture comprising a compound of formula (LIIIA) as defined above and a compound of formula (LIIIB)
Figure imgf000036_0001
(LIIIB)
wherein R3 and R4 and preferences thereof are as defined for compounds of formula (IA), and each X independently represents CI, Br or I, and wherein the mixture is enriched for compounds of formula (LIIIA).
Another group of novel intermediates are compounds of formula (LVA)
Figure imgf000036_0002
(LVA)
wherein R , R , A , A , A and A are as defined for compounds of formula (IA) and Px is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 and Px (when Px is P) are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides a mixture comprising a compound of formula (LVA) as defined above and a compound of formula (LVB)
Figure imgf000036_0003
(LVB) wherein R3, R4, A1, A2, A3 and A4 and preferences thereof are as defined for compounds of formula (IA), and Px is as defined for the compound of formula (XXVA), and wherein the mixture is enriched for compounds of formula (LVA).
One group of compounds of formula (LVA) are compounds of (LVAa)
Figure imgf000037_0001
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) and XB is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
The invention also provides a mixture comprising a compound of formula (LVAa) as defined above and a compound of formula (LVBa)
Figure imgf000037_0002
wherein R3, R4 , A1, A2, A3, A4 and preferences thereof are as defined for the compound of formula (IA) and XB is as defined for the compound of formula (XXVA), and wherein the mixture is enriched for compounds of formula (LVAa).
Another group of compounds of formula (LVA) are compounds of (LVAb)
Figure imgf000037_0003
wherein R1, R2, R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA), or a salt or N- oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA). The invention also provides a mixture comprising a compound of formula (LVAb) as defined above and a compound of formula (LVBb)
Figure imgf000038_0001
wherein R1, R2, R3, R4 , A1, A2, A3, A4 and preferences thereof are as defined for the compound of formula (IA), and wherein the mixture is enriched for compounds of formula (LVAb).
Another group of compounds of formula (LVA) are compounds of (LVAc)
Figure imgf000038_0002
(LVAc)
wherein A1, A2, A3, A4, R3 and R4 are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula I. The preferences for A1, A2, A3, A4, R3, R4 and heterocyclyl are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides a mixture comprising a compound of formula (LVAc) as defined above and a compound of formula (LVBc)
Figure imgf000038_0003
(LVBc) ^ wherein A1, A2, A3, A4, R3 and R4 and preferences thereof are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula (IA), and wherein the mixture is enriched for compounds of formula (LVAc).
The invention also provides compounds of formula (LVIA)
Figure imgf000039_0001
wherein R3, R4 , A1, A2, A3 and A4 are as defined for compounds of formula (IA) and Px is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4 , A1, A2, A3, A4 and Px (when Px is P) are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides a mixture comprising a compound of formula (LIXAa) as defined above and a compound of formula (LIXBa)
Figure imgf000039_0002
wherein R3, R4 , A1, A2, A3, A4 and preferences thereof are as defined for the compound of formula (IA) and Px is as defined for the compound of formula (XXVA), and wherein the mixture is enriched for compounds of formula (LVIA).
One group of compounds of formula (LVIA) are compounds of (LVIAa)
H
Figure imgf000039_0003
(LVIAa) wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) and XB is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
The invention also provides a mixture comprising a compound of formula (LVIAa) as defined above and a compound of formula (LVIBa)
Figure imgf000040_0001
(LVIBa)
wherein R3, R4 , A1, A2, A3, A4 and preferences thereof are as defined for the compound of formula (IA) and XB is as defined for the compound of formula (XXVA), and wherein the mixture is enriched for the compound of formula (LVIAa)
Another group of compounds of formula (LVIA) are compounds of (LVIAb)
Figure imgf000040_0002
(LVIAb)
wherein R1, R2, R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA), or a salt or N- oxide thereof. The preferences for R1, R2, R3, R4, A1, A2, A3, A4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
The invention also provides a mixture comprising a compound of formula (LVIAb) as defined above and a compound of formula (LVIBb)
Figure imgf000040_0003
(LVIBb)
wherein R1, R2, R3, R4 , A1, A2, A3, A4 and preferences thereof are as defined for the compound of formula (IA), and wherein the mixture is enriched for compounds of formula (LVIAb).
Another group of compounds of formula (LVIA) are compounds of (LVIAc)
Figure imgf000040_0004
(LVIAc)
wherein A1, A2, A3, A4, R3 and R4 are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula (IA). The preferences for A1, A2, A3, A4, R3, R4 and heterocyclyl are the same as the preferences set out for the corresponding substituents of a compound of formula (IA). The invention also provides a mixture comprising a compound of formula (LVIAc) as defined above and a compound of formula (LVIBc)
Figure imgf000041_0001
(LVIBc) wherein A1, A2, A3, A4, R3 and R4 and preferences thereof are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula (IA), and wherein the mixture is enriched for compounds of formula (LVIAc).
In enriched mixtures of the invention, (also including the compounds described in the tables below), the molar proportion of the enriched compound in the mixture (e.g. the compound of formula (IA)) compared to the total amount of both compounds (e.g. the total amount of the compound of formula (IA) and the compound of formula ((IB)) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%. This also applies to the intermediate mixtures described above.
Racemic mixtures of compounds of formula (IA) are disclosed in PCT/EP2011/051284. This application is incorporated by reference.
The compounds in the Tables below illustrate the compounds of the invention. (Although the compounds in the tables below use different substituent identifiers for substituents as compared to the comopunds described above, the identity of the compounds is clear.)
Table G
Group number R2
G.001 ethyl-
G.002 butyl-
G.003 but-2-yl-
G.004 3-bromo-propyl-
G.005 2,2,2-trifluoro-ethyl-
G.006 3 ,3 , 3 -trifluoro -propyl-
G.007 2-methoxy-ethyl-
G.008 1 -methoxy-prop-2-yl-
G.009 cyclobutyl-
G.010 2-methyl-cyclohex- 1 -yl-
G.011 phenyl-methyl-
G.012 1 -phenyl-eth- 1 -yl-
G.013 2-phenyl-eth- 1 -yl-
G.014 (3-chloro-phenyl)-methyl-
G.015 (2-fluoro-phenyl)-methyl-
G.016 (4-methoxy-phenyl)-methyl-
G.017 (2-trifluoromethyl-phenyl)-methyl- Group number R2
G.018 (2-trifluoromethoxy-phenyl)-methyl-
G.019 (pyrid-2-yl)-methyl-
G.020 (pyrid-3-yl)-methyl-
G.021 (2-chloro-pyrid-5-yl)-methyl-
G.022 (l-methyl-lH-imidazol-4-yl)-methyl-
G.023 (furan-2-yl)-methyl-
G.024 2-(thiophen-2'-yl)-eth-l -yl-
G.025 2-(indol-3'-yl)-eth-l -yl-
G.026 ( lH-benzimidazol-2-yl) -methyl-
G.027 (oxetan-2 -yl) -methyl-
G.028 (tetrahydrofuran-2-yl)-methyl-
G.029 2-([ 1 ',3 '] dioxolan-2'-yl) -eth- 1 -yl-
G.030 2-(morpholin-4'-yl)-eth-l-yl-
G.031 2-(benzo[l',3']dioxol-5'-yl)-eth-l -yl-
G.032 (2,3-dihydro-benzo[l,4]dioxin-6-yl)-methyl-
G.033 2-chloro-phenyl-
G.034 3-fluoro-phenyl-
G.035 2-methyl-phenyl-
G.036 2-chloro-6-methyl-phenyl-
G.037 2-trifluoromethyl-phenyl-
G.038 2,4-dimethoxy-phenyl-
G.039 3-methyl-pyrid-2-yl-
G.040 1 ,3-dimethyl-lH-pyrazol-5-yl-
G.041 4-methyl-thiazol-2-yl-
G.042 5-methyl-thiadiazol-2-yl-
G.043 quinolin-2-yl-
G.044 quinolin-5-yl-
G.045 benzothiazol-6-yl-
G.046 4-methyl-benzothiazol-2-yl-
G.047 thietan-3-yl-
G.048 1 -oxo-thietan-3-yl-
G.049 1 , 1 -dioxo-thietan-3-yl-
G.050 3 -methyl -thietan-3 -yl-
G.051 N-(2,2,2-Trifluoro-ethyl)-acetamide-2-yl
G.052 thietan-2-yl-methyl-
G.053 1 -oxo-thietan-2-yl-methyl-
G.054 1 , 1 -dioxo-thietan-2-yl-methyl-
G.055 thietan-3 -yl-methyl-
G.056 1 -oxo-thietan-3-yl-methyl-
G.057 1 , 1 -dioxo-thietan-3 -yl-methyl-
G.058 thietan-3 -yl-ethyl-
G.059 1 -oxo-thietan-3-yl-ethyl-
G.060 1 , 1 -dioxo-thietan-3 -yl-ethyl- Group number R2
G.061 2-fluoro-cyclopropyl
G.062 n-Butyl
G.063 2-Methoxy-l -methyl-ethyl
G.064 1 -Oxo-thietan-3-yl
G.065 2-ethyl-isoxazolidin-3-one-4-yl
G.066 Dihydro-thiophen-2-one-3-yl
G.067 6-Ethoxycarbonyl-cyclohex-3-enyl
G.068 2-Benzylsulfanyl-ethyl
G.069 4-Methanesulfonyl-benzyl
G.070 Ν',Ν'-Dimethylamino-ethyl
G.071 sec-Butyl
G.072 Butan-l -ol-2-yl
G.073 2,2-Difluoro-ethyl
G.074 Ethynyl-cyclohexyl
G.075 2-Morpholin-4-yl-ethyl
G.076 3 -Pyrrolidin- 1 -yl -propyl
G.077 3 -Piperidin- 1 -yl -propyl
G.078 [3-(4-Chloro-phenyl)-isoxazol-5-yl] -methyl
G.079 Phenethyl
G.080 l,2,2,6,6-Pentamethyl-piperidin-4-yl
G.081 2-Phenoxy-ethyl
G.082 3-Chloro-benzyl
G.083 2-Acetylamino-ethyl
G.084 4-Pyrazol- 1 -yl -benzyl
G.085 2-Methylsulfanyl-ethyl
G.086 2-Piperidin- 1 -yl -benzyl
G.087 4-Phenoxy-benzyl
G.088 (6-Chloro-pyridin-3 -yl)-methyl
G.089 1 -Benzyl-pyrrolidin-3 -yl
G.090 2-(4-Benzyl-piperazin- 1 -yl)-ethyl
G.091 Furan-2-yl-methyl
G.092 lH-Indazol-5-yl
G.093 4-Pyrrol-l -yl -phenyl
G.094 4-Piperidin- 1 -yl -phenyl
G.095 2-Methylsulfanyl-phenyl
G.096 4-Methyl-2-oxo-2H-chromen-7-yl
G.097 4-Dimethylsulfamoyl-phenyl
G.098 2,5-Dimethyl-2H-pyrazol-3-yl
G.099 5-Methylsulfanyl-lH-[l,2,4]triazol-3-yl
G.100 4-Hydroxy-6-methyl-pyrimidin-2-yl
G.101 Quinolin-2-yl
G.102 5-Methyl-3 -phenyl -isoxazol-4-yl
G.103 9H-Purin-6-yl Group number R2
G.104 5-Acetyl-4-methyl-thiazol-2-yl
G.105 4-Methyl-benzothiazol-2-yl
G.106 5-Methyl-[l,3,4]thiadiazol-2-yl
G.107 4,6-Dimethyl-2H-pyrazolo[3,4-b]pyridin-3-yl
G.108 3-(2,2,2-Trifluoro-ethoxyimino)-cyclobutyl
G.109 2-Thietan-3 -yl-ethyl
G.110 2-(l , 1 -Dioxo-thietan-3 -yl)-ethyl
G.l l l 3-Oxo-2-(2,2,2-trifluoro-ethyl)-isoxazolidin-4-yl
G.112 H
G.113 H
G.114 2-(2,2,2-trifluoro-ethyl)-isoxazolidin-3-one-4-yl
G.115 2-(2,2-Difluoro-ethyl)-isoxazolidin-3-one-4-yl
G.116 2-(2-Fluoro-ethyl)-isoxazolidin-3-one-4-yl
Table P
Figure imgf000044_0001
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0015 chloro difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0016 chloro difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0017 chloro difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0018 chloro difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0019 chloro difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0020 chloro difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0021 chloro difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0022 chloro difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0023 chloro difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0024 chloro difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0025 chloro trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0026 chloro trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0027 chloro trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0028 chloro trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0029 chloro trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0030 chloro trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0031 chloro trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0032 chloro trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0033 chloro trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0034 chloro trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0035 chloro trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0036 chloro trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0037 hydrogen 1 bromo CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0038 hydrogen 1 chloro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0039 hydrogen 1 cyano CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0040 hydrogen 1 cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0041 hydrogen 1 ethyl CH, Y3 is CH
P.0042 X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy fluoro Y1 is CH, Y2 is hydrogen 1 CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0043 hydrogen 1 hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0044 hydrogen 1 methoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0045 hydrogen 1 methyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0046 hydrogen 1 nitro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0047 hydrogen 1 trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0048 hydrogen 1 trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0049 hydrogen difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0050 hydrogen difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0051 hydrogen difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0052 hydrogen difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0053 hydrogen difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0054 hydrogen difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0055 hydrogen difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0056 hydrogen difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0057 hydrogen difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0058 hydrogen difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0059 hydrogen difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0060 hydrogen difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0061 hydrogen trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0062 hydrogen trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0063 hydrogen trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0064 hydrogen trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0065 hydrogen trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0066 hydrogen trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0067 hydrogen trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0068 hydrogen trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0069 hydrogen trifluoromethyl methyl CH, Y3 is CH X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0070 hydrogen trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0071 hydrogen trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0072 hydrogen trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0073 is hydrogen 1 bromo CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0074 is hydrogen 1 chloro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0075 is hydrogen 1 cyano CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0076 is hydrogen 1 cyclopropyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0077 is hydrogen 1 ethyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0078 is hydrogen 1 fluoro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0079 is hydrogen 1 hydrogen CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0080 is hydrogen 1 methoxy CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0081 is hydrogen 1 methyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0082 is hydrogen 1 nitro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0083 is hydrogen 1 trifluoromethoxy CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0084 is hydrogen 1 trifluoromethyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0085 is hydrogen difluoromethyl bromo CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0086 is hydrogen difluoromethyl chloro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0087 is hydrogen difluoromethyl cyano CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0088 is hydrogen difluoromethyl cyclopropyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0089 is hydrogen difluoromethyl ethyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0090 is hydrogen difluoromethyl fluoro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0091 is hydrogen difluoromethyl hydrogen CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0092 is hydrogen difluoromethyl methoxy CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0093 is hydrogen difluoromethyl methyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0094 is hydrogen difluoromethyl nitro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0095 is hydrogen difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0096 is hydrogen difluoromethyl trifluoromethyl CH, Y3 is CH
P.0097 X1 is fluoro, X2 is C-Cl, X3 trifluoromethyl bromo Y1 is CH, Y2 is is hydrogen CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0098 is hydrogen trifluoromethyl chloro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0099 is hydrogen trifluoromethyl cyano CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0100 is hydrogen trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0101 is hydrogen trifluoromethyl ethyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0102 is hydrogen trifluoromethyl fluoro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0103 is hydrogen trifluoromethyl hydrogen CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0104 is hydrogen trifluoromethyl methoxy CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0105 is hydrogen trifluoromethyl methyl CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0106 is hydrogen trifluoromethyl nitro CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0107 is hydrogen trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0108 is hydrogen trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0109 is hydrogen 1 bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.01 10 is hydrogen 1 chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0111 is hydrogen 1 cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0112 is hydrogen 1 cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0113 is hydrogen 1 ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0114 is hydrogen 1 fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.01 15 is hydrogen 1 hydrogen CH, Y3 is CH
X1 is chioro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0116 is hydrogen 1 methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0117 is hydrogen 1 methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0118 is hydrogen 1 nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.01 19 is hydrogen 1 trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0120 is hydrogen 1 trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0121 is hydrogen difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0122 is hydrogen difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0123 is hydrogen difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0124 is hydrogen difluoromethyl cyclopropyl CH, Y3 is CH X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0125 is hydrogen difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0126 is hydrogen difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0127 is hydrogen difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0128 is hydrogen difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0129 is hydrogen difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0130 is hydrogen difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X Y1 is CH, Y2 is
P.0131 is hydrogen difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0132 is hydrogen difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0133 is hydrogen trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0134 is hydrogen trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X Y1 is CH, Y2 is
P.0135 is hydrogen trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0136 is hydrogen trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0137 is hydrogen trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0138 is hydrogen trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X Y1 is CH, Y2 is
P.0139 is hydrogen trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, Xi Y1 is CH, Y2 is
P.0140 is hydrogen trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0141 is hydrogen trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0142 is hydrogen trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X Y1 is CH, Y2 is
P.0143 is hydrogen trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, Xi Y1 is CH, Y2 is
P.0144 is hydrogen trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0145 is chloro 1 bromo CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0146 is chloro 1 chloro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0147 is chloro 1 cyano CH, Y3 is CH
X1 is chloro, X2 is C-Br, Xi chlorodifluoromethy Y1 is CH, Y2 is
P.0148 is chloro 1 cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0149 is chloro 1 ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0150 is chloro 1 fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0151 is chloro 1 hydrogen CH, Y3 is CH
P.0152 X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy methoxy Y1 is CH, Y2 is is chloro 1 CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0153 is chloro 1 methyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0154 is chloro 1 nitro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0155 is chloro 1 trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0156 is chloro 1 trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0157 is chloro difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0158 is chloro difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0159 is chloro difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0160 is chloro difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0161 is chloro difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0162 is chloro difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X Y1 is CH, Y2 is
P.0163 is chloro difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0164 is chloro difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0165 is chloro difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0166 is chloro difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0167 is chloro difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0168 is chloro difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0169 is chloro trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0170 is chloro trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0171 is chloro trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0172 is chloro trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0173 is chloro trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0174 is chloro trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0175 is chloro trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0176 is chloro trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0177 is chloro trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0178 is chloro trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0179 is chloro trifluoromethyl trifluoromethoxy CH, Y3 is CH X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.0180 is chloro trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0181 chloro 1 bromo CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0182 chloro 1 chloro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0183 chloro 1 cyano CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0184 chloro 1 cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0185 chloro 1 ethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0186 chloro 1 fluoro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0187 chloro 1 hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0188 chloro 1 methoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0189 chloro 1 methyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0190 chloro 1 nitro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0191 chloro 1 trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0192 chloro 1 trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0193 chloro difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0194 chloro difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0195 chloro difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0196 chloro difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0197 chloro difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0198 chloro difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0199 chloro difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0200 chloro difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0201 chloro difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0202 chloro difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0203 chloro difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0204 chloro difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0205 chloro trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0206 chloro trifluoromethyl chloro CH, Y3 is CH
P.0207 X1 is chloro, X2 is C-F, X3 is trifluoromethyl cyano Y1 is CH, Y2 is chloro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0208 chloro trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0209 chloro trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0210 chloro trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0211 chloro trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0212 chloro trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0213 chloro trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0214 chloro trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0215 chloro trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0216 chloro trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0217 is chloro 1 bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0218 is chloro 1 chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0219 is chloro 1 cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0220 is chloro 1 cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0221 is chloro 1 ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0222 is chloro 1 fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0223 is chloro 1 hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0224 is chloro 1 methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0225 is chloro 1 methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0226 is chloro 1 nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0227 is chloro 1 trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0228 is chloro 1 trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0229 is chloro difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0230 is chloro difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0231 is chloro difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0232 is chloro difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0233 is chloro difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0234 is chloro difluoromethyl fluoro CH, Y3 is CH X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0235 is chloro difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0236 is chloro difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0237 is chloro difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0238 is chloro difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0239 is chloro difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0240 is chloro difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0241 is chloro trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0242 is chloro trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0243 is chloro trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0244 is chloro trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0245 is chloro trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0246 is chloro trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0247 is chloro trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0248 is chloro trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0249 is chloro trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0250 is chloro trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0251 is chloro trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0252 is chloro trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0253 chloro 1 bromo CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0254 chloro 1 chloro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0255 chloro 1 cyano CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0256 chloro 1 cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-I, Xs is chlorodifluoromethy Y1 is CH, Y2 is
P.0257 chloro 1 ethyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0258 chloro 1 fluoro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0259 chloro 1 hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0260 chloro 1 methoxy CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0261 chloro 1 methyl CH, Y3 is CH
P.0262 X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy nitro Y1 is CH, Y2 is chloro 1 CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0263 chloro 1 trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0264 chloro 1 trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0265 chloro difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0266 chloro difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0267 chloro difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0268 chloro difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0269 chloro difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0270 chloro difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y- is
P.0271 chloro difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0272 chloro difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0273 chloro difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0274 chloro difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0275 chloro difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0276 chloro difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0277 chloro trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0278 chloro trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0279 chloro trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0280 chloro trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0281 chloro trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0282 chloro trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0283 chloro trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0284 chloro trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0285 chloro trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0286 chloro trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0287 chloro trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.0288 chloro trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0289 fluoro 1 bromo CH, Y3 is CH X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0290 fluoro 1 chloro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0291 fluoro 1 cyano CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0292 fluoro 1 cyclopropyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0293 fluoro 1 ethyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0294 fluoro 1 fluoro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0295 fluoro 1 hydrogen CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0296 fluoro 1 methoxy CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0297 fluoro 1 methyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0298 fluoro 1 nitro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0299 fluoro 1 trifluoromethoxy CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0300 fluoro 1 trifluoromethyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0301 fluoro difluoromethyl bromo CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0302 fluoro difluoromethyl chloro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0303 fluoro difluoromethyl cyano CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0304 fluoro difluoromethyl cyclopropyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0305 fluoro difluoromethyl ethyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0306 fluoro difluoromethyl fluoro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0307 fluoro difluoromethyl hydrogen CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0308 fluoro difluoromethyl methoxy CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0309 fluoro difluoromethyl methyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0310 fluoro difluoromethyl nitro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0311 fluoro difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0312 fluoro difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0313 fluoro trifluoromethyl bromo CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0314 fluoro trifluoromethyl chloro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0315 fluoro trifluoromethyl cyano CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0316 fluoro trifluoromethyl cyclopropyl CH, Y3 is CH
P.0317 X1 is fluoro, X2 is C-F, X3 is trifluoromethyl ethyl Y1 is CH, Y2 is fluoro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0318 fluoro trifluoromethyl fluoro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0319 fluoro trifluoromethyl hydrogen CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0320 fluoro trifluoromethyl methoxy CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0321 fluoro trifluoromethyl methyl CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0322 fluoro trifluoromethyl nitro CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0323 fluoro trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.0324 fluoro trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0325 bromo 1 bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0326 bromo 1 chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0327 bromo 1 cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0328 bromo 1 cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0329 bromo 1 ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0330 bromo 1 fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0331 bromo 1 hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0332 bromo 1 methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0333 bromo 1 methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0334 bromo 1 nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0335 bromo 1 trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0336 bromo 1 trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0337 bromo difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0338 bromo difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0339 bromo difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0340 bromo difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0341 bromo difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0342 bromo difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0343 bromo difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0344 bromo difluoromethyl methoxy CH, Y3 is CH X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0345 bromo difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0346 bromo difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0347 bromo difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0348 bromo difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0349 bromo trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0350 bromo trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0351 bromo trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0352 bromo trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0353 bromo trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0354 bromo trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0355 bromo trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0356 bromo trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0357 bromo trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0358 bromo trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0359 bromo trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0360 bromo trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0361 bromo 1 bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0362 bromo 1 chloro CH, Y3 is CH
X1 is chloro, X2 is CH, Xs is chlorodifluoromethy Y1 is CH, Y2 is
P.0363 bromo 1 cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0364 bromo 1 cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0365 bromo 1 ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0366 bromo 1 fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0367 bromo 1 hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0368 bromo 1 methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0369 bromo 1 methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0370 bromo 1 nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0371 bromo 1 trifluoromethoxy CH, Y3 is CH
P.0372 X1 is chloro, X2 is CH, X3 is chlorodifluoromethy trifluoromethyl Y1 is CH, Y2 is bromo 1 CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0373 bromo difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0374 bromo difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0375 bromo difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0376 bromo difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0377 bromo difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0378 bromo difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0379 bromo difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0380 bromo difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0381 bromo difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0382 bromo difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0383 bromo difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0384 bromo difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0385 bromo trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0386 bromo trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0387 bromo trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0388 bromo trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0389 bromo trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0390 bromo trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0391 bromo trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0392 bromo trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0393 bromo trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0394 bromo trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0395 bromo trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0396 bromo trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0397 bromo 1 bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0398 bromo 1 chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0399 bromo 1 cyano CH, Y3 is CH X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0400 bromo 1 cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0401 bromo 1 ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0402 bromo 1 fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0403 bromo 1 hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0404 bromo 1 methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0405 bromo 1 methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0406 bromo 1 nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0407 bromo 1 trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0408 bromo 1 trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0409 bromo difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0410 bromo difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.041 1 bromo difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0412 bromo difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0413 bromo difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0414 bromo difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0415 bromo difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0416 bromo difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0417 bromo difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0418 bromo difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0419 bromo difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0420 bromo difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0421 bromo trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0422 bromo trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0423 bromo trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0424 bromo trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0425 bromo trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0426 bromo trifluoromethyl fluoro CH, Y3 is CH
P.0427 X1 is chloro, X2 is CH, X3 is trifluoromethyl hydrogen Y1 is CH, Y2 is bromo CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0428 bromo trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0429 bromo trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0430 bromo trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0431 bromo trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.0432 bromo trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0433 is trifluoromethyl 1 bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0434 is trifluoromethyl 1 chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0435 is trifluoromethyl 1 cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0436 is trifluoromethyl 1 cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0437 is trifluoromethyl 1 ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0438 is trifluoromethyl 1 fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0439 is trifluoromethyl 1 hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0440 is trifluoromethyl 1 methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0441 is trifluoromethyl 1 methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0442 is trifluoromethyl 1 nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0443 is trifluoromethyl 1 trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.0444 is trifluoromethyl 1 trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0445 is trifluoromethyl difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0446 is trifluoromethyl difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0447 is trifluoromethyl difluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0448 is trifluoromethyl difluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0449 is trifluoromethyl difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0450 is trifluoromethyl difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0451 is trifluoromethyl difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0452 is trifluoromethyl difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0453 is trifluoromethyl difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0454 is trifluoromethyl difluoromethyl nitro CH, Y3 is CH X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0455 is trifluoromethyl difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0456 is trifluoromethyl difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0457 is trifluoromethyl trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0458 is trifluoromethyl trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0459 is trifluoromethyl trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0460 is trifluoromethyl trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0461 is trifluoromethyl trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0462 is trifluoromethyl trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0463 is trifluoromethyl trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0464 is trifluoromethyl trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0465 is trifluoromethyl trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0466 is trifluoromethyl trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0467 is trifluoromethyl trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.0468 is trifluoromethyl trifluoromethyl trifluoromethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0469 CH, X3 is trifluoromethyl 1 bromo CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0470 CH, X3 is trifluoromethyl 1 chloro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0471 CH, X3 is trifluoromethyl 1 cyano CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0472 CH, X3 is trifluoromethyl 1 cyclopropyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0473 CH, X3 is trifluoromethyl 1 ethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0474 CH, X3 is trifluoromethyl 1 fluoro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0475 CH, X3 is trifluoromethyl 1 hydrogen CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0476 CH, X3 is trifluoromethyl 1 methoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0477 CH, X3 is trifluoromethyl 1 methyl CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0478 CH, X3 is trifluoromethyl 1 nitro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0479 CH, X3 is trifluoromethyl 1 trifluoromethoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0480 CH, X3 is trifluoromethyl 1 trifluoromethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0481 CH, X3 is trifluoromethyl difluoromethyl bromo CH, Y3 is CH
P.0482 X1 is trifluoromethyl, X2 is difluoromethyl chloro Y1 is CH, Y2 is CH, X3 is trifluoromethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0483 CH, X3 is trifluoromethyl difluoromethyl cyano CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0484 CH, X3 is trifluoromethyl difluoromethyl cyclopropyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0485 CH, X3 is trifluoromethyl difluoromethyl ethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0486 CH, X3 is trifluoromethyl difluoromethyl fluoro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0487 CH, X3 is trifluoromethyl difluoromethyl hydrogen CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0488 CH, X3 is trifluoromethyl difluoromethyl methoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0489 CH, X3 is trifluoromethyl difluoromethyl methyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0490 CH, X3 is trifluoromethyl difluoromethyl nitro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0491 CH, X3 is trifluoromethyl difluoromethyl trifluoromethoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0492 CH, X3 is trifluoromethyl difluoromethyl trifluoromethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0493 CH, X3 is trifluoromethyl trifluoromethyl bromo CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0494 CH, X3 is trifluoromethyl trifluoromethyl chloro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0495 CH, X3 is trifluoromethyl trifluoromethyl cyano CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0496 CH, X3 is trifluoromethyl trifluoromethyl cyclopropyl CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0497 CH, X3 is trifluoromethyl trifluoromethyl ethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0498 CH, X3 is trifluoromethyl trifluoromethyl fluoro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0499 CH, X3 is trifluoromethyl trifluoromethyl hydrogen CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0500 CH, X3 is trifluoromethyl trifluoromethyl methoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0501 CH, X3 is trifluoromethyl trifluoromethyl methyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is
P.0502 CH, X3 is trifluoromethyl trifluoromethyl nitro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0503 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is
P.0504 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0505 CH, X3 is trifluoromethyl 1 bromo CH, Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0506 CH, X3 is trifluoromethyl 1 chloro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0507 CH, X3 is trifluoromethyl 1 cyano CH, Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0508 CH, X3 is trifluoromethyl 1 cyclopropyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0509 CH, X3 is trifluoromethyl 1 ethyl CH, Y3 is CH X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0510 CH, X3 is trifluoromethyl 1 fluoro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0511 CH, X3 is trifluoromethyl 1 hydrogen CH, Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0512 CH, X3 is trifluoromethyl 1 methoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0513 CH, X3 is trifluoromethyl 1 methyl CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0514 CH, X3 is trifluoromethyl 1 nitro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0515 CH, X3 is trifluoromethyl 1 trifluoromethoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0516 CH, X3 is trifluoromethyl 1 trifluoromethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0517 CH, X3 is trifluoromethyl difluoromethyl bromo CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0518 CH, X3 is trifluoromethyl difluoromethyl chloro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0519 CH, X3 is trifluoromethyl difluoromethyl cyano CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0520 CH, X3 is trifluoromethyl difluoromethyl cyclopropyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0521 CH, X3 is trifluoromethyl difluoromethyl ethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0522 CH, X3 is trifluoromethyl difluoromethyl fluoro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0523 CH, X3 is trifluoromethyl difluoromethyl hydrogen CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0524 CH, X3 is trifluoromethyl difluoromethyl methoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0525 CH, X3 is trifluoromethyl difluoromethyl methyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0526 CH, X3 is trifluoromethyl difluoromethyl nitro CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0527 CH, X3 is trifluoromethyl difluoromethyl trifluoromethoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0528 CH, X3 is trifluoromethyl difluoromethyl trifluoromethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0529 CH, X3 is trifluoromethyl trifluoromethyl bromo CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0530 CH, X3 is trifluoromethyl trifluoromethyl chloro CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0531 CH, X3 is trifluoromethyl trifluoromethyl cyano CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0532 CH, X3 is trifluoromethyl trifluoromethyl cyclopropyl CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0533 CH, X3 is trifluoromethyl trifluoromethyl ethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0534 CH, X3 is trifluoromethyl trifluoromethyl fluoro CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0535 CH, X3 is trifluoromethyl trifluoromethyl hydrogen CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0536 CH, X3 is trifluoromethyl trifluoromethyl methoxy CH, Y3 is CH
P.0537 X1 is trifluoromethyl, X2 is trifluoromethyl methyl Y1 is CH, Y2 is CH, X3 is trifluoromethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0538 CH, X3 is trifluoromethyl trifluoromethyl nitro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0539 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0540 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0541 CH, X3 is hydrogen 1 bromo CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0542 CH, X3 is hydrogen 1 chloro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0543 CH, X3 is hydrogen 1 cyano CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0544 CH, X3 is hydrogen 1 cyclopropyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0545 CH, X3 is hydrogen 1 ethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0546 CH, X3 is hydrogen 1 fluoro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0547 CH, X3 is hydrogen 1 hydrogen CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0548 CH, X3 is hydrogen 1 methoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0549 CH, X3 is hydrogen 1 methyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0550 CH, X3 is hydrogen 1 nitro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0551 CH, X3 is hydrogen 1 trifluoromethoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0552 CH, X3 is hydrogen 1 trifluoromethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0553 CH, X3 is hydrogen difluoromethyl bromo CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0554 CH, X3 is hydrogen difluoromethyl chloro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0555 CH, X3 is hydrogen difluoromethyl cyano CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0556 CH, X3 is hydrogen difluoromethyl cyclopropyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is
P.0557 CH, X3 is hydrogen difluoromethyl ethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0558 CH, X3 is hydrogen difluoromethyl fluoro CH, Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is
P.0559 CH, X3 is hydrogen difluoromethyl hydrogen CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0560 CH, X3 is hydrogen difluoromethyl methoxy CH, Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is
P.0561 CH, X3 is hydrogen difluoromethyl methyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0562 CH, X3 is hydrogen difluoromethyl nitro CH, Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is
P.0563 CH, X3 is hydrogen difluoromethyl trifluoromethoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0564 CH, X3 is hydrogen difluoromethyl trifluoromethyl CH, Y3 is CH X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is
P.0565 CH, X3 is hydrogen trifluoromethyl bromo CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0566 CH, X3 is hydrogen trifluoromethyl chloro CH, Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is
P.0567 CH, X3 is hydrogen trifluoromethyl cyano CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0568 CH, X3 is hydrogen trifluoromethyl cyclopropyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0569 CH, X3 is hydrogen trifluoromethyl ethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0570 CH, X3 is hydrogen trifluoromethyl fluoro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0571 CH, X3 is hydrogen trifluoromethyl hydrogen CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0572 CH, X3 is hydrogen trifluoromethyl methoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0573 CH, X3 is hydrogen trifluoromethyl methyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0574 CH, X3 is hydrogen trifluoromethyl nitro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0575 CH, X3 is hydrogen trifluoromethyl trifluoromethoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0576 CH, X3 is hydrogen trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0577 chloro 1 bromo CH, Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0578 chloro 1 chloro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0579 chloro 1 cyano CH, Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0580 chloro 1 cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0581 chloro 1 ethyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0582 chloro 1 fluoro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0583 chloro 1 hydrogen CH, Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0584 chloro 1 methoxy CH, Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0585 chloro 1 methyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0586 chloro 1 nitro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0587 chloro 1 trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.0588 chloro 1 trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0589 chloro difluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0590 chloro difluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0591 chloro difluoromethyl cyano CH, Y3 is CH
P.0592 X1 is chloro, X2 is N, X3 is difluoromethyl cyclopropyl Y1 is CH, Y2 is chloro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0593 chloro difluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0594 chloro difluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0595 chloro difluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0596 chloro difluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0597 chloro difluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0598 chloro difluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0599 chloro difluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0600 chloro difluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0601 chloro trifluoromethyl bromo CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0602 chloro trifluoromethyl chloro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0603 chloro trifluoromethyl cyano CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0604 chloro trifluoromethyl cyclopropyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0605 chloro trifluoromethyl ethyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0606 chloro trifluoromethyl fluoro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0607 chloro trifluoromethyl hydrogen CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0608 chloro trifluoromethyl methoxy CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0609 chloro trifluoromethyl methyl CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0610 chloro trifluoromethyl nitro CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0611 chloro trifluoromethyl trifluoromethoxy CH, Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.0612 chloro trifluoromethyl trifluoromethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0613 N, X3 is trifluoromethyl 1 bromo CH, Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0614 N, X3 is trifluoromethyl 1 chloro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0615 N, X3 is trifluoromethyl 1 cyano CH, Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0616 N, X3 is trifluoromethyl 1 cyclopropyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0617 N, X3 is trifluoromethyl 1 ethyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0618 N, X3 is trifluoromethyl 1 fluoro CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.0619 N, X3 is trifluoromethyl 1 hydrogen CH, Y3 is CH X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0620 N, X3 is trifluoromethyl 1 methoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0621 N, X3 is trifluoromethyl 1 methyl CH, Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0622 N, X3 is trifluoromethyl 1 nitro CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0623 N, X3 is trifluoromethyl 1 trifluoromethoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.0624 N, X3 is trifluoromethyl 1 trifluoromethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0625 N, X3 is trifluoromethyl difluoromethyl bromo CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0626 N, X3 is trifluoromethyl difluoromethyl chloro CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0627 N, X3 is trifluoromethyl difluoromethyl cyano CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0628 N, X3 is trifluoromethyl difluoromethyl cyclopropyl CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0629 N, X3 is trifluoromethyl difluoromethyl ethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0630 N, X3 is trifluoromethyl difluoromethyl fluoro CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0631 N, X3 is trifluoromethyl difluoromethyl hydrogen CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0632 N, X3 is trifluoromethyl difluoromethyl methoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0633 N, X3 is trifluoromethyl difluoromethyl methyl CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0634 N, X3 is trifluoromethyl difluoromethyl nitro CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0635 N, X3 is trifluoromethyl difluoromethyl trifluoromethoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0636 N, X3 is trifluoromethyl difluoromethyl trifluoromethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0637 N, X3 is trifluoromethyl trifluoromethyl bromo CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0638 N, X3 is trifluoromethyl trifluoromethyl chloro CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0639 N, X3 is trifluoromethyl trifluoromethyl cyano CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0640 N, X3 is trifluoromethyl trifluoromethyl cyclopropyl CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0641 N, X3 is trifluoromethyl trifluoromethyl ethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0642 N, X3 is trifluoromethyl trifluoromethyl fluoro CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0643 N, X3 is trifluoromethyl trifluoromethyl hydrogen CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0644 N, X3 is trifluoromethyl trifluoromethyl methoxy CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0645 N, X3 is trifluoromethyl trifluoromethyl methyl CH, Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.0646 N, X3 is trifluoromethyl trifluoromethyl nitro CH, Y3 is CH
P.0647 X1 is trifluoromethyl, X2 is trifluoromethyl trifluoromethoxy Y1 is CH, Y2 is N, X3 is trifluoromethyl CH, Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.0648 N, X3 is trifluoromethyl trifluoromethyl trifluoromethyl CH, Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0649 chloro 1 bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0650 chloro 1 chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0651 chloro 1 cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0652 chloro 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0653 chloro 1 ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0654 chloro 1 fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0655 chloro 1 hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0656 chloro 1 methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0657 chloro 1 methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0658 chloro 1 nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0659 chloro 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0660 chloro 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0661 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0662 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0663 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0664 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0665 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0666 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0667 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0668 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0669 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0670 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0671 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0672 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0673 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0674 chloro trifluoromethyl chloro Y3 is CH X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0675 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0676 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0677 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0678 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0679 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0680 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0681 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, Xs is Y1 is N, Y2 is CH,
P.0682 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0683 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0684 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0685 hydrogen 1 bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0686 hydrogen 1 chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0687 hydrogen 1 cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0688 hydrogen 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0689 hydrogen 1 ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0690 hydrogen 1 fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0691 hydrogen 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0692 hydrogen 1 methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0693 hydrogen 1 methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0694 hydrogen 1 nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0695 hydrogen 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0696 hydrogen 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0697 hydrogen difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0698 hydrogen difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0699 hydrogen difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0700 hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0701 hydrogen difluoromethyl ethyl Y3 is CH
P.0702 X1 is chloro, X2 is C-F, X3 is difluoromethyl fluoro Y1 is N, Y2 is CH, hydrogen Y3 is CH
X1 is chloro, X is C-F, X3 is Y1 is N, Y2 is CH,
P.0703 hydrogen difluoromethyl hydrogen Y3 is CH
X1 is chloro, X' is C-F, X3 is Y1 is N, Y2 is CH,
P.0704 hydrogen difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0705 hydrogen difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0706 hydrogen difluoromethyl nitro Y3 is CH
X1 is chloro, X is C-F, X3 is Y1 is N, Y2 is CH,
P.0707 hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0708 hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0709 hydrogen trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0710 hydrogen trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0711 hydrogen trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0712 hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0713 hydrogen trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0714 hydrogen trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0715 hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0716 hydrogen trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0717 hydrogen trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, XJ is Yl is N, Y2 is CH,
P.0718 hydrogen trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0719 hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0720 hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0721 is hydrogen 1 bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0722 is hydrogen 1 chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0723 is hydrogen 1 cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0724 is hydrogen 1 cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0725 is hydrogen 1 ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0726 is hydrogen 1 fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0727 is hydrogen 1 hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0728 is hydrogen 1 methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0729 is hydrogen 1 methyl Y3 is CH X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0730 is hydrogen 1 nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0731 is hydrogen 1 trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0732 is hydrogen 1 trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0733 is hydrogen difluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0734 is hydrogen difluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0735 is hydrogen difluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0736 is hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0737 is hydrogen difluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0738 is hydrogen difluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0739 is hydrogen difluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0740 is hydrogen difluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0741 is hydrogen difluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0742 is hydrogen difluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0743 is hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0744 is hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0745 is hydrogen trifluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0746 is hydrogen trifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0747 is hydrogen trifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0748 is hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0749 is hydrogen trifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0750 is hydrogen trifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0751 is hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0752 is hydrogen trifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0753 is hydrogen trifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0754 is hydrogen trifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0755 is hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0756 is hydrogen trifluoromethyl trifluoromethyl Y3 is CH
P.0757 X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy bromo Y1 is N, Y2 is CH, is hydrogen 1 Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0758 is hydrogen 1 chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0759 is hydrogen 1 cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0760 is hydrogen 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0761 is hydrogen 1 ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0762 is hydrogen 1 fluoro Y3 is CH
X1 is chioro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0763 is hydrogen 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0764 is hydrogen 1 methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0765 is hydrogen 1 methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0766 is hydrogen 1 nitro Y3 is CH
X1 is chioro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0767 is hydrogen 1 trifluoromethoxy Y3 is CH
X1 is chioro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0768 is hydrogen 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0769 is hydrogen difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0770 is hydrogen difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0771 is hydrogen difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0772 is hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0773 is hydrogen difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0774 is hydrogen difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0775 is hydrogen difluoromethyl hydrogen Y3 is CH
X1 is chioro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0776 is hydrogen difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0777 is hydrogen difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0778 is hydrogen difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0779 is hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0780 is hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0781 is hydrogen trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0782 is hydrogen trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0783 is hydrogen trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0784 is hydrogen trifluoromethyl cyclopropyl Y3 is CH X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0785 is hydrogen trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0786 is hydrogen trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0787 is hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0788 is hydrogen trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0789 is hydrogen trifluoromethyl methyl Y3 is CH
X1 is chioro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0790 is hydrogen trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0791 is hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0792 is hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0793 is chloro 1 bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0794 is chloro 1 chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0795 is chloro 1 cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0796 is chloro 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0797 is chloro 1 ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0798 is chloro 1 fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0799 is chloro 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0800 is chloro 1 methoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0801 is chloro 1 methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0802 is chloro 1 nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0803 is chloro 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0804 is chloro 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0805 is chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0806 is chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0807 is chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0808 is chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0809 is chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0810 is chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0811 is chloro difluoromethyl hydrogen Y3 is CH
P.0812 X1 is chloro, X2 is C-Br, X3 difluoromethyl methoxy Y1 is N, Y2 is CH, is chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0813 is chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0814 is chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0815 is chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0816 is chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0817 is chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0818 is chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0819 is chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0820 is chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0821 is chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0822 is chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0823 is chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0824 is chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0825 is chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0826 is chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0827 is chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is CH,
P.0828 is chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0829 chloro 1 bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0830 chloro 1 chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0831 chloro 1 cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0832 chloro 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0833 chloro 1 ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0834 chloro 1 fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0835 chloro 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0836 chloro 1 methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0837 chloro 1 methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0838 chloro 1 nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0839 chloro 1 trifluoromethoxy Y3 is CH X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0840 chloro 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0841 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0842 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0843 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0844 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0845 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0846 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0847 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0848 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0849 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0850 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0851 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0852 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0853 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0854 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0855 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0856 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0857 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0858 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0859 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0860 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0861 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0862 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0863 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0864 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0865 is chloro 1 bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0866 is chloro 1 chloro Y3 is CH
P.0867 X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy cyano Y1 is N, Y2 is CH, is chloro 1 Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0868 is chloro 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0869 is chloro 1 ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0870 is chloro 1 fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0871 is chloro 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0872 is chloro 1 methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0873 is chloro 1 methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0874 is chloro 1 nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0875 is chloro 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.0876 is chloro 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0877 is chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0878 is chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0879 is chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0880 is chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0881 is chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0882 is chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0883 is chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0884 is chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0885 is chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0886 is chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0887 is chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0888 is chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0889 is chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0890 is chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0891 is chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0892 is chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0893 is chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0894 is chloro trifluoromethyl fluoro Y3 is CH X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0895 is chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0896 is chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0897 is chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0898 is chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0899 is chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.0900 is chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0901 chloro 1 bromo Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0902 chloro 1 chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0903 chloro 1 cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0904 chloro 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0905 chloro 1 ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0906 chloro 1 fluoro Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0907 chloro 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0908 chloro 1 methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0909 chloro 1 methyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0910 chloro 1 nitro Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0911 chloro 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0912 chloro 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0913 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0914 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0915 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0916 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0917 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0918 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0919 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0920 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0921 chloro difluoromethyl methyl Y3 is CH
P.0922 X1 is chloro, X2 is C-I, X3 is difluoromethyl nitro Y1 is N, Y2 is CH, chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0923 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0924 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0925 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0926 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0927 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0928 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0929 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0930 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0931 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0932 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0933 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0934 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0935 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is CH,
P.0936 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0937 fluoro 1 bromo Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0938 fluoro 1 chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0939 fluoro 1 cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0940 fluoro 1 cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0941 fluoro 1 ethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0942 fluoro 1 fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0943 fluoro 1 hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0944 fluoro 1 methoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0945 fluoro 1 methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0946 fluoro 1 nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0947 fluoro 1 trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0948 fluoro 1 trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0949 fluoro difluoromethyl bromo Y3 is CH X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0950 fluoro difluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0951 fluoro difluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0952 fluoro difluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0953 fluoro difluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0954 fluoro difluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0955 fluoro difluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0956 fluoro difluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0957 fluoro difluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0958 fluoro difluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0959 fluoro difluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0960 fluoro difluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0961 fluoro trifluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0962 fluoro trifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0963 fluoro trifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0964 fluoro trifluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0965 fluoro trifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0966 fluoro trifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0967 fluoro trifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0968 fluoro trifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0969 fluoro trifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0970 fluoro trifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0971 fluoro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is CH,
P.0972 fluoro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0973 bromo 1 bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0974 bromo 1 chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0975 bromo 1 cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0976 bromo 1 cyclopropyl Y3 is CH
P.0977 X1 is chloro, X2 is CH, X3 is chlorodifluoromethy ethyl Y1 is N, Y2 is CH, bromo 1 Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0978 bromo 1 fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0979 bromo 1 hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0980 bromo 1 methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0981 bromo 1 methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0982 bromo 1 nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0983 bromo 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.0984 bromo 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0985 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0986 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0987 bromo difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0988 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0989 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0990 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0991 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0992 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0993 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0994 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0995 bromo difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0996 bromo difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0997 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0998 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.0999 bromo trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1000 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1001 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1002 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1003 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1004 bromo trifluoromethyl methoxy Y3 is CH X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1005 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1006 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1007 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1008 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1009 bromo 1 bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1010 bromo 1 chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1011 bromo 1 cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1012 bromo 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1013 bromo 1 ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1014 bromo 1 fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1015 bromo 1 hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1016 bromo 1 methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1017 bromo 1 methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1018 bromo 1 nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1019 bromo 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1020 bromo 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1021 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1022 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1023 bromo difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1024 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1025 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1026 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1027 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1028 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1029 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1030 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1031 bromo difluoromethyl trifluoromethoxy Y3 is CH
P.1032 X1 is chloro, X2 is CH, X3 is difluoromethyl trifluoromethyl Y1 is N, Y2 is CH, bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1033 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1034 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1035 bromo trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1036 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1037 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1038 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1039 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1040 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1041 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1042 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1043 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1044 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1045 bromo 1 bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1046 bromo 1 chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1047 bromo 1 cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1048 bromo 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1049 bromo 1 ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1050 bromo 1 fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1051 bromo 1 hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1052 bromo 1 methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1053 bromo 1 methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1054 bromo 1 nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1055 bromo 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1056 bromo 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1057 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1058 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1059 bromo difluoromethyl cyano Y3 is CH X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1060 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1061 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1062 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1063 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1064 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1065 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1066 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1067 bromo difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1068 bromo difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1069 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1070 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1071 bromo trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1072 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1073 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1074 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1075 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1076 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1077 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1078 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1079 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is CH,
P.1080 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.1081 is trifluoromethyl 1 bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.1082 is trifluoromethyl 1 chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.1083 is trifluoromethyl 1 cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.1084 is trifluoromethyl 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.1085 is trifluoromethyl 1 ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.1086 is trifluoromethyl 1 fluoro Y3 is CH
P.1087 X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy hydrogen Y1 is N, Y2 is CH, is trifluoromethyl 1 Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.1088 is trifluoromethyl 1 methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.1089 is trifluoromethyl 1 methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.1090 is trifluoromethyl 1 nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.1091 is trifluoromethyl 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is CH,
P.1092 is trifluoromethyl 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1093 is trifluoromethyl difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1094 is trifluoromethyl difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1095 is trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1096 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1097 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1098 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1099 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1 100 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1101 is trifluoromethyl difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1102 is trifluoromethyl difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1103 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1104 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1 105 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1106 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1107 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1108 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1109 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1 110 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.l l l l is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1112 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1113 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1 1 14 is trifluoromethyl trifluoromethyl nitro Y3 is CH X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1115 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is CH,
P.1116 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1117 CH, X3 is trifluoromethyl 1 bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1118 CH, X3 is trifluoromethyl 1 chloro Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1119 CH, X3 is trifluoromethyl 1 cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1120 CH, X3 is trifluoromethyl 1 cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1121 CH, X3 is trifluoromethyl 1 ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1122 CH, X3 is trifluoromethyl 1 fluoro Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1123 CH, X3 is trifluoromethyl 1 hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1124 CH, X3 is trifluoromethyl 1 methoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1125 CH, X3 is trifluoromethyl 1 methyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1126 CH, X3 is trifluoromethyl 1 nitro Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1127 CH, X3 is trifluoromethyl 1 trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1128 CH, X3 is trifluoromethyl 1 trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is CH,
P.1129 CH, X3 is trifluoromethyl difluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is CH,
P.1130 CH, X3 is trifluoromethyl difluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1131 CH, X3 is trifluoromethyl difluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is CH,
P.1132 CH, X3 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1133 CH, X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is CH,
P.1134 CH, X3 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1135 CH, X3 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is CH,
P.1136 CH, X3 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1137 CH, X3 is trifluoromethyl difluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is CH,
P.1138 CH, X3 is trifluoromethyl difluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1139 CH, X3 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is CH,
P.1140 CH, X3 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1141 CH, X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
P.1142 X1 is trifluoromethyl, X2 is trifluoromethyl chloro Y1 is N, Y2 is CH, CH, X3 is trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1143 CH, X3 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1144 CH, X3 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1145 CH, X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1146 CH, X3 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1147 CH, X3 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1148 CH, X3 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1149 CH, X3 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1150 CH, X3 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1151 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1152 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1153 CH, X3 is trifluoromethyl 1 bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1154 CH, X3 is trifluoromethyl 1 chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1155 CH, X3 is trifluoromethyl 1 cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1156 CH, X3 is trifluoromethyl 1 cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1157 CH, X3 is trifluoromethyl 1 ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1158 CH, X3 is trifluoromethyl 1 fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1159 CH, X3 is trifluoromethyl 1 hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1160 CH, X3 is trifluoromethyl 1 methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1161 CH, X3 is trifluoromethyl 1 methyl Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1162 CH, X3 is trifluoromethyl 1 nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1163 CH, X3 is trifluoromethyl 1 trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1164 CH, X3 is trifluoromethyl 1 trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1165 CH, X3 is trifluoromethyl difluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is CH,
P.1166 CH, X3 is trifluoromethyl difluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1167 CH, X3 is trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is CH,
P.1168 CH, X3 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1169 CH, X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH X1 is trifluoromethyl, X2 is Y1 is N, Y2 is CH,
P.1170 CH, X3 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1171 CH, X3 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is CH,
P.1172 CH, X3 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1173 CH, X3 is trifluoromethyl difluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is CH,
P.1174 CH, X3 is trifluoromethyl difluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1175 CH, X3 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is CH,
P.1176 CH, X3 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1177 CH, X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is CH,
P.1178 CH, X3 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1179 CH, X3 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is CH,
P.1180 CH, X3 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1181 CH, X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is CH,
P.1182 CH, X3 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1183 CH, X3 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is CH,
P.1184 CH, X3 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is CH,
P.1185 CH, X3 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1186 CH, X3 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is CH,
P.1187 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1188 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1189 CH, X3 is hydrogen 1 bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1190 CH, X3 is hydrogen 1 chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1191 CH, X3 is hydrogen 1 cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1192 CH, X3 is hydrogen 1 cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1193 CH, X3 is hydrogen 1 ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1194 CH, X3 is hydrogen 1 fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1195 CH, X3 is hydrogen 1 hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1196 CH, X3 is hydrogen 1 methoxy Y3 is CH
P.1197 X1 is trifluoromethyl, X2 is chlorodifluoromethy methyl Y1 is N, Y2 is CH,
Figure imgf000088_0001
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1225 chloro 1 bromo Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1226 chloro 1 chloro Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1227 chloro 1 cyano Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1228 chloro 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1229 chloro 1 ethyl Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1230 chloro 1 fluoro Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1231 chloro 1 hydrogen Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1232 chloro 1 methoxy Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1233 chloro 1 methyl Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1234 chloro 1 nitro Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1235 chloro 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1236 chloro 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1237 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1238 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1239 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1240 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1241 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1242 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1243 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1244 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1245 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1246 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1247 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1248 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1249 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1250 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1251 chloro trifluoromethyl cyano Y3 is CH
P.1252 X1 is chloro, X2 is N, X3 is trifluoromethyl cyclopropyl Y1 is N, Y2 is CH, chloro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1253 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1254 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1255 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1256 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1257 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1258 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1259 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is CH,
P.1260 chloro trifluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1261 N, X3 is trifluoromethyl 1 bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1262 N, X3 is trifluoromethyl 1 chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1263 N, X3 is trifluoromethyl 1 cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1264 N, X3 is trifluoromethyl 1 cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1265 N, X3 is trifluoromethyl 1 ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1266 N, X3 is trifluoromethyl 1 fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1267 N, X3 is trifluoromethyl 1 hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1268 N, X3 is trifluoromethyl 1 methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1269 N, X3 is trifluoromethyl 1 methyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1270 N, X3 is trifluoromethyl 1 nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1271 N, X3 is trifluoromethyl 1 trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is N, Y2 is CH,
P.1272 N, X3 is trifluoromethyl 1 trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1273 N, X3 is trifluoromethyl difluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is CH,
P.1274 N, X3 is trifluoromethyl difluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1275 N, X3 is trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is CH,
P.1276 N, X3 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1277 N, X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is CH,
P.1278 N, X3 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1279 N, X3 is trifluoromethyl difluoromethyl hydrogen Y3 is CH X1 is trifluoromethyl, X2 is Y1 is N, Y2 is CH,
P.1280 N, X3 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1281 N, X3 is trifluoromethyl difluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is CH,
P.1282 N, X3 is trifluoromethyl difluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1283 N, X3 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1284 N, X3 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1285 N, X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1286 N, X3 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1287 N, X3 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1288 N, X3 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1289 N, X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1290 N, X3 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1291 N, X3 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1292 N, X3 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1293 N, X3 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X is Y1 is N, Y2 is CH,
P.1294 N, X3 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X is Y1 is N, Y2 is CH,
P.1295 N, X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is CH,
P.1296 N, X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1297 chloro 1 bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1298 chloro 1 chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1299 chloro 1 cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1300 chloro 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1301 chloro 1 ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1302 chloro 1 fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1303 chloro 1 hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1304 chloro 1 methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1305 chloro 1 methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1306 chloro 1 nitro Y3 is CH
P.1307 X1 is chloro, X2 is CH, X3 is chlorodifluoromethy trifluoromethoxy Y1 is N, Y2 is N, chloro 1 Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1308 chloro 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1309 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1310 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1311 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1312 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1313 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1314 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1315 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1316 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1317 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1318 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1319 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1320 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1321 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1322 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1323 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1324 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1325 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1326 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1327 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1328 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1329 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1330 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1331 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1332 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1333 hydrogen 1 bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1334 hydrogen 1 chloro Y3 is CH X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1335 hydrogen 1 cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1336 hydrogen 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1337 hydrogen 1 ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1338 hydrogen 1 fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1339 hydrogen 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1340 hydrogen 1 methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1341 hydrogen 1 methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1342 hydrogen 1 nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1343 hydrogen 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1344 hydrogen 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1345 hydrogen difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1346 hydrogen difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1347 hydrogen difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1348 hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1349 hydrogen difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1350 hydrogen difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1351 hydrogen difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1352 hydrogen difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1353 hydrogen difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1354 hydrogen difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1355 hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1356 hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1357 hydrogen trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1358 hydrogen trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1359 hydrogen trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1360 hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1361 hydrogen trifluoromethyl ethyl Y3 is CH
P.1362 X1 is chloro, X2 is C-F, X3 is trifluoromethyl fluoro Y1 is N, Y2 is N, hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1363 hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1364 hydrogen trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1365 hydrogen trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1366 hydrogen trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1367 hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1368 hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1369 is hydrogen 1 bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1370 is hydrogen 1 chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1371 is hydrogen 1 cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1372 is hydrogen 1 cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1373 is hydrogen 1 ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1374 is hydrogen 1 fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1375 is hydrogen 1 hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1376 is hydrogen 1 methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1377 is hydrogen 1 methyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1378 is hydrogen 1 nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1379 is hydrogen 1 trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1380 is hydrogen 1 trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1381 is hydrogen difluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1382 is hydrogen difluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1383 is hydrogen difluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1384 is hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1385 is hydrogen difluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1386 is hydrogen difluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1387 is hydrogen difluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1388 is hydrogen difluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1389 is hydrogen difluoromethyl methyl Y3 is CH X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1390 is hydrogen difluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1391 is hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1392 is hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1393 is hydrogen trifluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1394 is hydrogen trifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1395 is hydrogen trifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1396 is hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1397 is hydrogen trifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1398 is hydrogen trifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1399 is hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1400 is hydrogen trifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1401 is hydrogen trifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1402 is hydrogen trifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1403 is hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1404 is hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1405 is hydrogen 1 bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1406 is hydrogen 1 chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1407 is hydrogen 1 cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1408 is hydrogen 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1409 is hydrogen 1 ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1410 is hydrogen 1 fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1411 is hydrogen 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1412 is hydrogen 1 methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1413 is hydrogen 1 methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1414 is hydrogen 1 nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1415 is hydrogen 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1416 is hydrogen 1 trifluoromethyl Y3 is CH
P.1417 X1 is chloro, X2 is C-Cl, X3 difluoromethyl bromo Y1 is N, Y2 is N, is hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1418 is hydrogen difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1419 is hydrogen difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1420 is hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1421 is hydrogen difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1422 is hydrogen difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1423 is hydrogen difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1424 is hydrogen difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1425 is hydrogen difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1426 is hydrogen difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1427 is hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1428 is hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1429 is hydrogen trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1430 is hydrogen trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1431 is hydrogen trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1432 is hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1433 is hydrogen trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1434 is hydrogen trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1435 is hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1436 is hydrogen trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1437 is hydrogen trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1438 is hydrogen trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1439 is hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1440 is hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1441 is chloro 1 bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1442 is chloro 1 chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1443 is chloro 1 cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1444 is chloro 1 cyclopropyl Y3 is CH X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1445 is chloro 1 ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1446 is chloro 1 fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1447 is chloro 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1448 is chloro 1 methoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1449 is chloro 1 methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1450 is chloro 1 nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1451 is chloro 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1452 is chloro 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1453 is chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1454 is chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1455 is chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1456 is chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1457 is chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1458 is chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1459 is chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1460 is chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1461 is chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1462 is chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1463 is chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1464 is chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1465 is chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1466 is chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1467 is chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1468 is chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1469 is chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1470 is chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1471 is chloro trifluoromethyl hydrogen Y3 is CH
P.1472 X1 is chloro, X2 is C-Br, X3 trifluoromethyl methoxy Y1 is N, Y2 is N, is chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1473 is chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1474 is chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1475 is chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is N, Y2 is N,
P.1476 is chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1477 chloro 1 bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1478 chloro 1 chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1479 chloro 1 cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1480 chloro 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1481 chloro 1 ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1482 chloro 1 fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1483 chloro 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1484 chloro 1 methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1485 chloro 1 methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1486 chloro 1 nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1487 chloro 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1488 chloro 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1489 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1490 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1491 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1492 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1493 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1494 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1495 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1496 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1497 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1498 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1499 chloro difluoromethyl trifluoromethoxy Y3 is CH X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1500 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1501 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1502 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1503 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1504 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1505 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1506 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1507 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1508 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1509 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1510 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1511 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1512 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1513 is chloro 1 bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1514 is chloro 1 chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1515 is chloro 1 cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1516 is chloro 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1517 is chloro 1 ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1518 is chloro 1 fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1519 is chloro 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1520 is chloro 1 methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1521 is chloro 1 methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1522 is chloro 1 nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1523 is chloro 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1524 is chloro 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1525 is chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1526 is chloro difluoromethyl chloro Y3 is CH
P.1527 X1 is chloro, X2 is C-Cl, X3 difluoromethyl cyano Y1 is N, Y2 is N, is chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1528 is chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1529 is chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1530 is chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1531 is chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1532 is chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1533 is chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1534 is chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1535 is chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1536 is chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1537 is chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1538 is chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1539 is chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1540 is chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1541 is chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1542 is chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1543 is chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1544 is chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1545 is chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1546 is chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1547 is chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1548 is chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1549 chloro 1 bromo Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1550 chloro 1 chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1551 chloro 1 cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1552 chloro 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1553 chloro 1 ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1554 chloro 1 fluoro Y3 is CH X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1555 chloro 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1556 chloro 1 methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1557 chloro 1 methyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1558 chloro 1 nitro Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1559 chloro 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1560 chloro 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1561 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1562 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1563 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1564 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1565 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1566 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1567 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1568 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1569 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1570 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1571 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1572 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, Xs is Y1 is N, Y2 is N,
P.1573 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1574 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1575 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1576 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1577 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1578 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1579 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1580 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1581 chloro trifluoromethyl methyl Y3 is CH
P.1582 X1 is chloro, X2 is C-I, X3 is trifluoromethyl nitro Y1 is N, Y2 is N, chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1583 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is N, Y2 is N,
P.1584 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1585 fluoro 1 bromo Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1586 fluoro 1 chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1587 fluoro 1 cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1588 fluoro 1 cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1589 fluoro 1 ethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1590 fluoro 1 fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1591 fluoro 1 hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1592 fluoro 1 methoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1593 fluoro 1 methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1594 fluoro 1 nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1595 fluoro 1 trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1596 fluoro 1 trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1597 fluoro difluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1598 fluoro difluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1599 fluoro difluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1600 fluoro difluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1601 fluoro difluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1602 fluoro difluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1603 fluoro difluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1604 fluoro difluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1605 fluoro difluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1606 fluoro difluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1607 fluoro difluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1608 fluoro difluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1609 fluoro trifluoromethyl bromo Y3 is CH X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1610 fluoro trifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1611 fluoro trifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1612 fluoro trifluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1613 fluoro trifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1614 fluoro trifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1615 fluoro trifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1616 fluoro trifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1617 fluoro trifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1618 fluoro trifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1619 fluoro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is N, Y2 is N,
P.1620 fluoro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1621 bromo 1 bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1622 bromo 1 chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1623 bromo 1 cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1624 bromo 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1625 bromo 1 ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1626 bromo 1 fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1627 bromo 1 hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1628 bromo 1 methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1629 bromo 1 methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1630 bromo 1 nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1631 bromo 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1632 bromo 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1633 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1634 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1635 bromo difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1636 bromo difluoromethyl cyclopropyl Y3 is CH
P.1637 X1 is chloro, X2 is CH, X3 is difluoromethyl ethyl Y1 is N, Y2 is N, bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1638 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1639 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1640 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1641 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1642 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1643 bromo difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1644 bromo difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1645 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1646 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1647 bromo trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1648 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1649 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1650 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1651 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1652 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1653 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1654 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1655 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1656 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1657 bromo 1 bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1658 bromo 1 chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1659 bromo 1 cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1660 bromo 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1661 bromo 1 ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1662 bromo 1 fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1663 bromo 1 hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1664 bromo 1 methoxy Y3 is CH X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1665 bromo 1 methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1666 bromo 1 nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1667 bromo 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1668 bromo 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1669 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1670 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1671 bromo difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1672 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1673 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1674 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1675 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1676 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1677 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1678 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1679 bromo difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1680 bromo difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1681 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1682 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1683 bromo trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1684 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1685 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1686 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1687 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1688 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1689 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1690 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1691 bromo trifluoromethyl trifluoromethoxy Y3 is CH
P.1692 X1 is chloro, X2 is CH, X3 is trifluoromethyl trifluoromethyl Y1 is N, Y2 is N, bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1693 bromo 1 bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1694 bromo 1 chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1695 bromo 1 cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1696 bromo 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1697 bromo 1 ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1698 bromo 1 fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1699 bromo 1 hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1700 bromo 1 methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1701 bromo 1 methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1702 bromo 1 nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1703 bromo 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1704 bromo 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1705 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1706 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1707 bromo difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1708 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1709 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1710 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1711 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1712 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1713 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1714 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1715 bromo difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1716 bromo difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1717 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1718 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1719 bromo trifluoromethyl cyano Y3 is CH X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1720 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X is Y1 is N, Y2 is N,
P.1721 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1722 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1723 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1724 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1725 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1726 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1727 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is N, Y2 is N,
P.1728 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1729 is trifluoromethyl 1 bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1730 is trifluoromethyl 1 chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1731 is trifluoromethyl 1 cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1732 is trifluoromethyl 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1733 is trifluoromethyl 1 ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1734 is trifluoromethyl 1 fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1735 is trifluoromethyl 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1736 is trifluoromethyl 1 methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1737 is trifluoromethyl 1 methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1738 is trifluoromethyl 1 nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1739 is trifluoromethyl 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is N, Y2 is N,
P.1740 is trifluoromethyl 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1741 is trifluoromethyl difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1742 is trifluoromethyl difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1743 is trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1744 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1745 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1746 is trifluoromethyl difluoromethyl fluoro Y3 is CH
P.1747 X1 is chloro, X2 is C-Cl, X3 difluoromethyl hydrogen Y1 is N, Y2 is N, is trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1748 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1749 is trifluoromethyl difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1750 is trifluoromethyl difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1751 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1752 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1753 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1754 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1755 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1756 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1757 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1758 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1759 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1760 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1761 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1762 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1763 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is N, Y2 is N,
P.1764 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1765 CH, X3 is trifluoromethyl 1 bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1766 CH, X3 is trifluoromethyl 1 chloro Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1767 CH, X3 is trifluoromethyl 1 cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1768 CH, X3 is trifluoromethyl 1 cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1769 CH, X3 is trifluoromethyl 1 ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1770 CH, X3 is trifluoromethyl 1 fluoro Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1771 CH, X3 is trifluoromethyl 1 hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1772 CH, X3 is trifluoromethyl 1 methoxy Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1773 CH, X3 is trifluoromethyl 1 methyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1774 CH, X3 is trifluoromethyl 1 nitro Y3 is CH X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1775 CH, X3 is trifluoromethyl 1 trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1776 CH, X3 is trifluoromethyl 1 trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is N,
P.1777 CH, X3 is trifluoromethyl difluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1778 CH, X3 is trifluoromethyl difluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1779 CH, X3 is trifluoromethyl difluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1780 CH, X3 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1781 CH, X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1782 CH, X3 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1783 CH, X3 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1784 CH, X3 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1785 CH, X3 is trifluoromethyl difluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1786 CH, X3 is trifluoromethyl difluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1787 CH, X3 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1788 CH, X3 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1789 CH, X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1790 CH, X3 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1791 CH, X3 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1792 CH, X3 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1793 CH, X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1794 CH, X3 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1795 CH, X3 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1796 CH, X3 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1797 CH, X3 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1798 CH, X3 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1799 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1800 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1801 CH, X3 is trifluoromethyl 1 bromo Y3 is CH
P.1802 X1 is trifluoromethyl, X2 is chlorodifluoromethy chloro Y1 is N, Y2 is N, CH, X3 is trifluoromethyl 1 Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1803 CH, X3 is trifluoromethyl 1 cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1804 CH, X3 is trifluoromethyl 1 cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1805 CH, X3 is trifluoromethyl 1 ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1806 CH, X3 is trifluoromethyl 1 fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1807 CH, X3 is trifluoromethyl 1 hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1808 CH, X3 is trifluoromethyl 1 methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1809 CH, X3 is trifluoromethyl 1 methyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1810 CH, X3 is trifluoromethyl 1 nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1811 CH, X3 is trifluoromethyl 1 trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1812 CH, X3 is trifluoromethyl 1 trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1813 CH, X3 is trifluoromethyl difluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1814 CH, X3 is trifluoromethyl difluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1815 CH, X3 is trifluoromethyl difluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1816 CH, X3 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1817 CH, X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1818 CH, X3 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1819 CH, X3 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1820 CH, X3 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1821 CH, X3 is trifluoromethyl difluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is N,
P.1822 CH, X3 is trifluoromethyl difluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1823 CH, X3 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is N,
P.1824 CH, X3 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1825 CH, X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is N,
P.1826 CH, X3 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1827 CH, X3 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is N,
P.1828 CH, X3 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1829 CH, X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH X1 is trifluoromethyl, X2 is Y1 is N, Y2 is N,
P.1830 CH, X3 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1831 CH, X3 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is N,
P.1832 CH, X3 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1833 CH, X3 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1834 CH, X3 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1835 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1836 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1837 CH, X3 is hydrogen 1 bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1838 CH, X3 is hydrogen 1 chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1839 CH, X3 is hydrogen 1 cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1840 CH, X3 is hydrogen 1 cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1841 CH, X3 is hydrogen 1 ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1842 CH, X3 is hydrogen 1 fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1843 CH, X3 is hydrogen 1 hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1844 CH, X3 is hydrogen 1 methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1845 CH, X3 is hydrogen 1 methyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1846 CH, X3 is hydrogen 1 nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1847 CH, X3 is hydrogen 1 trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1848 CH, X3 is hydrogen 1 trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1849 CH, X3 is hydrogen difluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1850 CH, X3 is hydrogen difluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1851 CH, X3 is hydrogen difluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1852 CH, X3 is hydrogen difluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1853 CH, X3 is hydrogen difluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1854 CH, X3 is hydrogen difluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1855 CH, X3 is hydrogen difluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1856 CH, X3 is hydrogen difluoromethyl methoxy Y3 is CH
P.1857 X1 is trifluoromethyl, X2 is difluoromethyl methyl Y1 is N, Y2 is N, CH, X3 is hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1858 CH, X3 is hydrogen difluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1859 CH, X3 is hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1860 CH, X3 is hydrogen difluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1861 CH, X3 is hydrogen trifluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1862 CH, X3 is hydrogen trifluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1863 CH, X3 is hydrogen trifluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1864 CH, X3 is hydrogen trifluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1865 CH, X3 is hydrogen trifluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1866 CH, X3 is hydrogen trifluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1867 CH, X3 is hydrogen trifluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1868 CH, X3 is hydrogen trifluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1869 CH, X3 is hydrogen trifluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1870 CH, X3 is hydrogen trifluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1871 CH, X3 is hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is N, Y2 is N,
P.1872 CH, X3 is hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1873 chloro 1 bromo Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1874 chloro 1 chloro Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1875 chloro 1 cyano Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1876 chloro 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1877 chloro 1 ethyl Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1878 chloro 1 fluoro Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1879 chloro 1 hydrogen Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1880 chloro 1 methoxy Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1881 chloro 1 methyl Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1882 chloro 1 nitro Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1883 chloro 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1884 chloro 1 trifluoromethyl Y3 is CH - I l l -
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1885 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1886 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1887 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1888 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1889 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1890 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1891 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1892 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1893 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1894 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1895 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1896 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1897 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1898 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1899 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1900 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1901 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1902 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1903 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1904 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1905 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1906 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1907 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is N, X3 is Y1 is N, Y2 is N,
P.1908 chloro trifluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1909 N, X3 is trifluoromethyl 1 bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1910 N, X3 is trifluoromethyl 1 chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1911 N, X3 is trifluoromethyl 1 cyano Y3 is CH
P.1912 X1 is trifluoromethyl, X2 is chlorodifluoromethy cyclopropyl Y1 is N, Y2 is N, N, X3 is trifluoromethyl 1 Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1913 N, X3 is trifluoromethyl 1 ethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1914 N, X3 is trifluoromethyl 1 fluoro Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1915 N, X3 is trifluoromethyl 1 hydrogen Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1916 N, X3 is trifluoromethyl 1 methoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1917 N, X3 is trifluoromethyl 1 methyl Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1918 N, X3 is trifluoromethyl 1 nitro Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1919 N, X3 is trifluoromethyl 1 trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is N, Y2 is N,
P.1920 N, X3 is trifluoromethyl 1 trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1921 N, X3 is trifluoromethyl difluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1922 N, X3 is trifluoromethyl difluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1923 N, X3 is trifluoromethyl difluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1924 N, X3 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1925 N, X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1926 N, X3 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1927 N, X3 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1928 N, X3 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1929 N, X3 is trifluoromethyl difluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1930 N, X3 is trifluoromethyl difluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1931 N, X3 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is N,
P.1932 N, X3 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1933 N, X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is N,
P.1934 N, X3 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1935 N, X3 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is N,
P.1936 N, X3 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1937 N, X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is N, Y2 is N,
P.1938 N, X3 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is N, Y2 is N,
P.1939 N, X3 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
Figure imgf000115_0001
chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1968 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1969 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1970 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1971 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X1 is Y1 is CH, Y2 is N,
P.1972 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1973 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1974 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1975 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1976 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1977 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1978 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1979 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.1980 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.1981 hydrogen 1 bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.1982 hydrogen 1 chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.1983 hydrogen 1 cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.1984 hydrogen 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.1985 hydrogen 1 ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.1986 hydrogen 1 fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.1987 hydrogen 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.1988 hydrogen 1 methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.1989 hydrogen 1 methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.1990 hydrogen 1 nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.1991 hydrogen 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.1992 hydrogen 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.1993 hydrogen difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.1994 hydrogen difluoromethyl chloro Y3 is CH X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.1995 hydrogen difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.1996 hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.1997 hydrogen difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.1998 hydrogen difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.1999 hydrogen difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2000 hydrogen difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2001 hydrogen difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2002 hydrogen difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2003 hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2004 hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2005 hydrogen trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2006 hydrogen trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, Xs is Y1 is CH, Y2 is N,
P.2007 hydrogen trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2008 hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2009 hydrogen trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2010 hydrogen trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2011 hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2012 hydrogen trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2013 hydrogen trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2014 hydrogen trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2015 hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2016 hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2017 is hydrogen 1 bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2018 is hydrogen 1 chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2019 is hydrogen 1 cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2020 is hydrogen 1 cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2021 is hydrogen 1 ethyl Y3 is CH
P.2022 X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy fluoro Y1 is CH, Y2 is N, is hydrogen 1 Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2023 is hydrogen 1 hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2024 is hydrogen 1 methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2025 is hydrogen 1 methyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2026 is hydrogen 1 nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2027 is hydrogen 1 trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2028 is hydrogen 1 trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2029 is hydrogen difluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2030 is hydrogen difluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2031 is hydrogen difluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2032 is hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2033 is hydrogen difluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2034 is hydrogen difluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2035 is hydrogen difluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2036 is hydrogen difluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2037 is hydrogen difluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2038 is hydrogen difluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2039 is hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2040 is hydrogen difluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2041 is hydrogen trifluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2042 is hydrogen trifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2043 is hydrogen trifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2044 is hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2045 is hydrogen trifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2046 is hydrogen trifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2047 is hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2048 is hydrogen trifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2049 is hydrogen trifluoromethyl methyl Y3 is CH , ,„
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
Ρ.2050 is hydrogen trifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2051 is hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
Ρ.2052 is hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
Ρ.2053 is hydrogen 1 bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
Ρ.2054 is hydrogen 1 chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
Ρ.2055 is hydrogen 1 cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
Ρ.2056 is hydrogen 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
Ρ.2057 is hydrogen 1 ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
Ρ.2058 is hydrogen 1 fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
Ρ.2059 is hydrogen 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
Ρ.2060 is hydrogen 1 methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2061 is hydrogen 1 methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
Ρ.2062 is hydrogen 1 nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
Ρ.2063 is hydrogen 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
Ρ.2064 is hydrogen 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
Ρ.2065 is hydrogen difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
Ρ.2066 is hydrogen difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
Ρ.2067 is hydrogen difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
Ρ.2068 is hydrogen difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
Ρ.2069 is hydrogen difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
Ρ.2070 is hydrogen difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2071 is hydrogen difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
Ρ.2072 is hydrogen difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
Ρ.2073 is hydrogen difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
Ρ.2074 is hydrogen difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
Ρ.2075 is hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
Ρ.2076 is hydrogen difluoromethyl trifluoromethyl Y3 is CH
Ρ.2077 X1 is chloro, X2 is C-Cl, X3 trifluoromethyl bromo Y1 is CH, Y2 is N, is hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2078 is hydrogen trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2079 is hydrogen trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2080 is hydrogen trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2081 is hydrogen trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2082 is hydrogen trifluoromethyl fluoro Y3 is CH
X1 is chioro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2083 is hydrogen trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2084 is hydrogen trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2085 is hydrogen trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2086 is hydrogen trifluoromethyl nitro Y3 is CH
X1 is chioro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2087 is hydrogen trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2088 is hydrogen trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2089 is chloro 1 bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2090 is chloro 1 chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2091 is chloro 1 cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2092 is chloro 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2093 is chloro 1 ethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2094 is chloro 1 fluoro Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2095 is chloro 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2096 is chloro 1 methoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2097 is chloro 1 methyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2098 is chloro 1 nitro Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2099 is chloro 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2100 is chloro 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is N,
P.2101 is chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is N,
P.2102 is chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is N,
P.2103 is chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is N,
P.2104 is chloro difluoromethyl cyclopropyl Y3 is CH
Figure imgf000121_0001
chloro 1 Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2133 chloro 1 methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2134 chloro 1 nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2135 chloro 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2136 chloro 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2137 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2138 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2139 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2140 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2141 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2142 chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2143 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2144 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2145 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2146 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2147 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2148 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2149 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2150 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2151 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2152 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2153 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2154 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2155 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2156 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2157 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2158 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2159 chloro trifluoromethyl trifluoromethoxy Y3 is CH X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2160 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-CI, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2161 is chloro 1 bromo Y3 is CH
X1 is chloro, X2 is C-CI, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2162 is chloro 1 chloro Y3 is CH
X1 is chloro, X2 is C-CI, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2163 is chloro 1 cyano Y3 is CH
X1 is chloro, X2 is C-CI, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2164 is chloro 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-CI, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2165 is chloro 1 ethyl Y3 is CH
X1 is chloro, X2 is C-CI, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2166 is chloro 1 fluoro Y3 is CH
X1 is chloro, X2 is C-CI, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2167 is chloro 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-CI, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2168 is chloro 1 methoxy Y3 is CH
X1 is chloro, X2 is C-CI, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2169 is chloro 1 methyl Y3 is CH
X1 is chloro, X2 is C-CI, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2170 is chloro 1 nitro Y3 is CH
X1 is chloro, X2 is C-CI, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2171 is chloro 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-CI, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2172 is chloro 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-CI, X3 Y1 is CH, Y2 is N,
P.2173 is chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-CI, X3 Y1 is CH, Y2 is N,
P.2174 is chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-CI, X3 Y1 is CH, Y2 is N,
P.2175 is chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-CI, X3 Y1 is CH, Y2 is N,
P.2176 is chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-CI, X3 Y1 is CH, Y2 is N,
P.2177 is chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-CI, X3 Y1 is CH, Y2 is N,
P.2178 is chloro difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-CI, X3 Y1 is CH, Y2 is N,
P.2179 is chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-CI, X3 Y1 is CH, Y2 is N,
P.2180 is chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-CI, X3 Y1 is CH, Y2 is N,
P.2181 is chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-CI, X3 Y1 is CH, Y2 is N,
P.2182 is chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-CI, X3 Y1 is CH, Y2 is N,
P.2183 is chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-CI, X3 Y1 is CH, Y2 is N,
P.2184 is chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-CI, X3 Y1 is CH, Y2 is N,
P.2185 is chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-CI, X3 Y1 is CH, Y2 is N,
P.2186 is chloro trifluoromethyl chloro Y3 is CH
P.2187 X1 is chloro, X2 is C-CI, X3 trifluoromethyl cyano Y1 is CH, Y2 is N, is chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2188 is chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2189 is chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2190 is chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2191 is chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2192 is chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2193 is chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2194 is chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2195 is chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2196 is chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2197 chloro 1 bromo Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2198 chloro 1 chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2199 chloro 1 cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2200 chloro 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2201 chloro 1 ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2202 chloro 1 fluoro Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2203 chloro 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2204 chloro 1 methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2205 chloro 1 methyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2206 chloro 1 nitro Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2207 chloro 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2208 chloro 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2209 chloro difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2210 chloro difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2211 chloro difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2212 chloro difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2213 chloro difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2214 chloro difluoromethyl fluoro Y3 is CH X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2215 chloro difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2216 chloro difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2217 chloro difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2218 chloro difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2219 chloro difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2220 chloro difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2221 chloro trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2222 chloro trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2223 chloro trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2224 chloro trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2225 chloro trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2226 chloro trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2227 chloro trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2228 chloro trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2229 chloro trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2230 chloro trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2231 chloro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is N,
P.2232 chloro trifluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2233 fluoro 1 bromo Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2234 fluoro 1 chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2235 fluoro 1 cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2236 fluoro 1 cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2237 fluoro 1 ethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2238 fluoro 1 fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2239 fluoro 1 hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2240 fluoro 1 methoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2241 fluoro 1 methyl Y3 is CH
P.2242 X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy nitro Y1 is CH, Y2 is N, fluoro 1 Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2243 fluoro 1 trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2244 fluoro 1 trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2245 fluoro difluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2246 fluoro difluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2247 fluoro difluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2248 fluoro difluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2249 fluoro difluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2250 fluoro difluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2251 fluoro difluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2252 fluoro difluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2253 fluoro difluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2254 fluoro difluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2255 fluoro difluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2256 fluoro difluoromethyl trifluoromethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2257 fluoro trifluoromethyl bromo Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2258 fluoro trifluoromethyl chloro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2259 fluoro trifluoromethyl cyano Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2260 fluoro trifluoromethyl cyclopropyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2261 fluoro trifluoromethyl ethyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2262 fluoro trifluoromethyl fluoro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2263 fluoro trifluoromethyl hydrogen Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2264 fluoro trifluoromethyl methoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2265 fluoro trifluoromethyl methyl Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2266 fluoro trifluoromethyl nitro Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2267 fluoro trifluoromethyl trifluoromethoxy Y3 is CH
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is N,
P.2268 fluoro trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2269 bromo 1 bromo Y3 is CH
Figure imgf000127_0001
bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2298 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2299 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2300 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X1 is Y1 is CH, Y2 is N,
P.2301 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X1 is Y1 is CH, Y2 is N,
P.2302 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2303 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2304 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2305 bromo 1 bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2306 bromo 1 chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2307 bromo 1 cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2308 bromo 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2309 bromo 1 ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2310 bromo 1 fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2311 bromo 1 hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2312 bromo 1 methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2313 bromo 1 methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2314 bromo 1 nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2315 bromo 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2316 bromo 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2317 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2318 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2319 bromo difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2320 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2321 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2322 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2323 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2324 bromo difluoromethyl methoxy Y3 is CH X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2325 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2326 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2327 bromo difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2328 bromo difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2329 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2330 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2331 bromo trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2332 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2333 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2334 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2335 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2336 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2337 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2338 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2339 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2340 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2341 bromo 1 bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2342 bromo 1 chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2343 bromo 1 cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2344 bromo 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2345 bromo 1 ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2346 bromo 1 fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2347 bromo 1 hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2348 bromo 1 methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2349 bromo 1 methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2350 bromo 1 nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2351 bromo 1 trifluoromethoxy Y3 is CH
P.2352 X1 is chloro, X2 is CH, X3 is chlorodifluoromethy trifluoromethyl Y1 is CH, Y2 is N, bromo 1 Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2353 bromo difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2354 bromo difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2355 bromo difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2356 bromo difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2357 bromo difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2358 bromo difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2359 bromo difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2360 bromo difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2361 bromo difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2362 bromo difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2363 bromo difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2364 bromo difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2365 bromo trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2366 bromo trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2367 bromo trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2368 bromo trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2369 bromo trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2370 bromo trifluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2371 bromo trifluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2372 bromo trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2373 bromo trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2374 bromo trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2375 bromo trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is N,
P.2376 bromo trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromemy Y1 is CH, Y2 is N,
P.2377 is trifluoromethyl 1 bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromemy Y1 is CH, Y2 is N,
P.2378 is trifluoromethyl 1 chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromemy Y1 is CH, Y2 is N,
P.2379 is trifluoromethyl 1 cyano Y3 is CH X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2380 is trifluoromethyl 1 cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2381 is trifluoromethyl 1 ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2382 is trifluoromethyl 1 fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2383 is trifluoromethyl 1 hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2384 is trifluoromethyl 1 methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, Xs chlorodifluoromethy Y1 is CH, Y2 is N,
P.2385 is trifluoromethyl 1 methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2386 is trifluoromethyl 1 nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2387 is trifluoromethyl 1 trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is N,
P.2388 is trifluoromethyl 1 trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, Xs Y1 is CH, Y2 is N,
P.2389 is trifluoromethyl difluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2390 is trifluoromethyl difluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X* Y1 is CH, Y2 is N,
P.2391 is trifluoromethyl difluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2392 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, Xs Y1 is CH, Y2 is N,
P.2393 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X Y1 is CH, Y2 is N,
P.2394 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2395 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X1 is chloro, X2 is C-Cl, Xs Y1 is CH, Y2 is N,
P.2396 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2397 is trifluoromethyl difluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2398 is trifluoromethyl difluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2399 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, Xs Y1 is CH, Y2 is N,
P.2400 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2401 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2402 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2403 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2404 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2405 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2406 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
P.2407 X1 is chloro, X2 is C-Cl, X3 trifluoromethyl hydrogen Y1 is CH, Y2 is N, is trifluoromethyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2408 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2409 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2410 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2411 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is N,
P.2412 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2413 CH, X3 is trifluoromethyl 1 bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2414 CH, X3 is trifluoromethyl 1 chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2415 CH, X3 is trifluoromethyl 1 cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2416 CH, X3 is trifluoromethyl 1 cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2417 CH, X3 is trifluoromethyl 1 ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2418 CH, X3 is trifluoromethyl 1 fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2419 CH, X3 is trifluoromethyl 1 hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2420 CH, X3 is trifluoromethyl 1 methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2421 CH, X3 is trifluoromethyl 1 methyl Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2422 CH, X3 is trifluoromethyl 1 nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2423 CH, X3 is trifluoromethyl 1 trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2424 CH, X3 is trifluoromethyl 1 trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2425 CH, X3 is trifluoromethyl difluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2426 CH, X3 is trifluoromethyl difluoromethyl chloro Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is N,
P.2427 CH, X3 is trifluoromethyl difluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2428 CH, X3 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is N,
P.2429 CH, X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2430 CH, X3 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is N,
P.2431 CH, X3 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2432 CH, X3 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is N,
P.2433 CH, X3 is trifluoromethyl difluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2434 CH, X3 is trifluoromethyl difluoromethyl nitro Y3 is CH X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is N,
P.2435 CH, X3 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2436 CH, X3 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is N,
P.2437 CH, X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2438 CH, X3 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2439 CH, X3 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2440 CH, X3 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2441 CH, X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2442 CH, X3 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2443 CH, X3 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2444 CH, X3 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2445 CH, X3 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2446 CH, X3 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2447 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2448 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2449 CH, X3 is trifluoromethyl 1 bromo Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2450 CH, X3 is trifluoromethyl 1 chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2451 CH, X3 is trifluoromethyl 1 cyano Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2452 CH, X3 is trifluoromethyl 1 cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2453 CH, X3 is trifluoromethyl 1 ethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2454 CH, X3 is trifluoromethyl 1 fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2455 CH, X3 is trifluoromethyl 1 hydrogen Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2456 CH, X3 is trifluoromethyl 1 methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2457 CH, X3 is trifluoromethyl 1 methyl Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2458 CH, X3 is trifluoromethyl 1 nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2459 CH, X3 is trifluoromethyl 1 trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2460 CH, X3 is trifluoromethyl 1 trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2461 CH, X3 is trifluoromethyl difluoromethyl bromo Y3 is CH
P.2462 X1 is trifluoromethyl, X2 is difluoromethyl chloro Y1 is CH, Y2 is N, CH, X3 is trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2463 CH, X3 is trifluoromethyl difluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2464 CH, X3 is trifluoromethyl difluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2465 CH, X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2466 CH, X3 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2467 CH, X3 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2468 CH, X3 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2469 CH, X3 is trifluoromethyl difluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2470 CH, X3 is trifluoromethyl difluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2471 CH, X3 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2472 CH, X3 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2473 CH, X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2474 CH, X3 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2475 CH, X3 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2476 CH, X3 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2477 CH, X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2478 CH, X3 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2479 CH, X3 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2480 CH, X3 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2481 CH, X3 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is N,
P.2482 CH, X3 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2483 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is N,
P.2484 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2485 CH, X3 is hydrogen 1 bromo Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2486 CH, X3 is hydrogen 1 chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2487 CH, X3 is hydrogen 1 cyano Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2488 CH, X3 is hydrogen 1 cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2489 CH, X3 is hydrogen 1 ethyl Y3 is CH X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2490 CH, X3 is hydrogen 1 fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2491 CH, X3 is hydrogen 1 hydrogen Y3 is CH
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2492 CH, X3 is hydrogen 1 methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2493 CH, X3 is hydrogen 1 methyl Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2494 CH, X3 is hydrogen 1 nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2495 CH, X3 is hydrogen 1 trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is N,
P.2496 CH, X3 is hydrogen 1 trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2497 CH, X3 is hydrogen difluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2498 CH, X3 is hydrogen difluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2499 CH, X3 is hydrogen difluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2500 CH, X3 is hydrogen difluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2501 CH, X3 is hydrogen difluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2502 CH, X3 is hydrogen difluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2503 CH, X3 is hydrogen difluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2504 CH, X3 is hydrogen difluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2505 CH, X3 is hydrogen difluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2506 CH, X3 is hydrogen difluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2507 CH, X3 is hydrogen difluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2508 CH, X3 is hydrogen difluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2509 CH, X3 is hydrogen trifluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2510 CH, X3 is hydrogen trifluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2511 CH, X3 is hydrogen trifluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2512 CH, X3 is hydrogen trifluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2513 CH, X3 is hydrogen trifluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2514 CH, X3 is hydrogen trifluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2515 CH, X3 is hydrogen trifluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is N,
P.2516 CH, X3 is hydrogen trifluoromethyl methoxy Y3 is CH
P.2517 X1 is trifluoromethyl, X2 is trifluoromethyl methyl Y1 is CH, Y2 is N,
Figure imgf000136_0001
Figure imgf000137_0001
N, X3 is trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2573 N, X3 is trifluoromethyl difluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2574 N, X3 is trifluoromethyl difluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2575 N, X3 is trifluoromethyl difluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2576 N, X3 is trifluoromethyl difluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2577 N, X3 is trifluoromethyl difluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2578 N, X3 is trifluoromethyl difluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2579 N, X3 is trifluoromethyl difluoromethyl trifluoromethoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2580 N, X3 is trifluoromethyl difluoromethyl trifluoromethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2581 N, X3 is trifluoromethyl trifluoromethyl bromo Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2582 N, X3 is trifluoromethyl trifluoromethyl chloro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2583 N, X3 is trifluoromethyl trifluoromethyl cyano Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2584 N, X3 is trifluoromethyl trifluoromethyl cyclopropyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2585 N, X3 is trifluoromethyl trifluoromethyl ethyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2586 N, X3 is trifluoromethyl trifluoromethyl fluoro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2587 N, X3 is trifluoromethyl trifluoromethyl hydrogen Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2588 N, X3 is trifluoromethyl trifluoromethyl methoxy Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2589 N, X3 is trifluoromethyl trifluoromethyl methyl Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2590 N, X3 is trifluoromethyl trifluoromethyl nitro Y3 is CH
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is N,
P.2591 N, X3 is trifluoromethyl trifluoromethyl trifluoromethoxy Y3 is CH
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is N,
P.2592 N, X3 is trifluoromethyl trifluoromethyl trifluoromethyl Y3 is CH
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2593 chloro 1 bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2594 chloro 1 chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2595 chloro 1 cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2596 chloro 1 cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2597 chloro 1 ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2598 chloro 1 fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2599 chloro 1 hydrogen CH, Y3 is N X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2600 chloro 1 mefhoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2601 chloro 1 methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2602 chloro 1 nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2603 chloro 1 trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2604 chloro 1 trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2605 chloro difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2606 chloro difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2607 chloro difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2608 chloro difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2609 chloro difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2610 chloro difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2611 chloro difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2612 chloro difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2613 chloro difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2614 chloro difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2615 chloro difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2616 chloro difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2617 chloro trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2618 chloro trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2619 chloro trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2620 chloro trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2621 chloro trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2622 chloro trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2623 chloro trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2624 chloro trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2625 chloro trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2626 chloro trifluoromethyl nitro CH, Y3 is N
P.2627 X1 is chloro, X2 is CH, X3 is trifluoromethyl trifluoromethoxy Y1 is CH, Y2 is chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2628 chloro trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2629 hydrogen 1 bromo CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2630 hydrogen 1 chloro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2631 hydrogen 1 cyano CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2632 hydrogen 1 cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2633 hydrogen 1 ethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2634 hydrogen 1 fluoro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2635 hydrogen 1 hydrogen CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2636 hydrogen 1 methoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2637 hydrogen 1 methyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2638 hydrogen 1 nitro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2639 hydrogen 1 trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2640 hydrogen 1 trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2641 hydrogen difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2642 hydrogen difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2643 hydrogen difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2644 hydrogen difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2645 hydrogen difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2646 hydrogen difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2647 hydrogen difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2648 hydrogen difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2649 hydrogen difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2650 hydrogen difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2651 hydrogen difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2652 hydrogen difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2653 hydrogen trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2654 hydrogen trifluoromethyl chloro CH, Y3 is N X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2655 hydrogen trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2656 hydrogen trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2657 hydrogen trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2658 hydrogen trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2659 hydrogen trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2660 hydrogen trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2661 hydrogen trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2662 hydrogen trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2663 hydrogen trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2664 hydrogen trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2665 is hydrogen 1 bromo CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2666 is hydrogen 1 chloro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2667 is hydrogen 1 cyano CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2668 is hydrogen 1 cyclopropyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2669 is hydrogen 1 ethyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2670 is hydrogen 1 fluoro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2671 is hydrogen 1 hydrogen CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2672 is hydrogen 1 methoxy CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2673 is hydrogen 1 methyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2674 is hydrogen 1 nitro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2675 is hydrogen 1 trifluoromethoxy CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2676 is hydrogen 1 trifluoromethyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2677 is hydrogen difluoromethyl bromo CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2678 is hydrogen difluoromethyl chloro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2679 is hydrogen difluoromethyl cyano CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2680 is hydrogen difluoromethyl cyclopropyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2681 is hydrogen difluoromethyl ethyl CH, Y3 is N
P.2682 X1 is fluoro, X2 is C-Cl, X3 difluoromethyl fluoro Y1 is CH, Y2 is is hydrogen CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2683 is hydrogen difluoromethyl hydrogen CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2684 is hydrogen difluoromethyl methoxy CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2685 is hydrogen difluoromethyl methyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2686 is hydrogen difluoromethyl nitro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2687 is hydrogen difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2688 is hydrogen difluoromethyl trifluoromethyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2689 is hydrogen trifluoromethyl bromo CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2690 is hydrogen trifluoromethyl chloro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2691 is hydrogen trifluoromethyl cyano CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2692 is hydrogen trifluoromethyl cyclopropyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2693 is hydrogen trifluoromethyl ethyl CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2694 is hydrogen trifluoromethyl fluoro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2695 is hydrogen trifluoromethyl hydrogen CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2696 is hydrogen trifluoromethyl methoxy CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2697 is hydrogen trifluoromethyl methyl CH, Y3 is N
X1 is fluoro, X- is C-Cl, X3 Y1 is CH, Y2 is
P.2698 is hydrogen trifluoromethyl nitro CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2699 is hydrogen trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is fluoro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2700 is hydrogen trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2701 is hydrogen 1 bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2702 is hydrogen 1 chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2703 is hydrogen 1 cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2704 is hydrogen 1 cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2705 is hydrogen 1 ethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2706 is hydrogen 1 fluoro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2707 is hydrogen 1 hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2708 is hydrogen 1 methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2709 is hydrogen 1 methyl CH, Y3 is N X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2710 is hydrogen 1 nitro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2711 is hydrogen 1 trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2712 is hydrogen 1 trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2713 is hydrogen difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2714 is hydrogen difluoromethyl chloro CH, Y3 is N
X1 is chioro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2715 is hydrogen difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2716 is hydrogen difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2717 is hydrogen difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2718 is hydrogen difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2719 is hydrogen difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2720 is hydrogen difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2721 is hydrogen difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2722 is hydrogen difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2723 is hydrogen difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2724 is hydrogen difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2725 is hydrogen trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2726 is hydrogen trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2727 is hydrogen trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2728 is hydrogen trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2729 is hydrogen trifluoromethyl ethyl CH, Y3 is N
X1 is chioro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2730 is hydrogen trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2731 is hydrogen trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2732 is hydrogen trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2733 is hydrogen trifluoromethyl methyl CH, Y3 is N
X1 is chioro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2734 is hydrogen trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2735 is hydrogen trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2736 is hydrogen trifluoromethyl trifluoromethyl CH, Y3 is N
P.2737 X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy bromo Y1 is CH, Y2 is is chloro 1 CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2738 is chloro 1 chloro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2739 is chloro 1 cyano CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2740 is chloro 1 cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2741 is chloro 1 ethyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2742 is chloro 1 fluoro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2743 is chloro 1 hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2744 is chloro 1 methoxy CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2745 is chloro 1 methyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2746 is chloro 1 nitro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2747 is chloro 1 trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2748 is chloro 1 trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2749 is chloro difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2750 is chloro difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2751 is chloro difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2752 is chloro difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2753 is chloro difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2754 is chloro difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2755 is chloro difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2756 is chloro difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2757 is chloro difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2758 is chloro difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2759 is chloro difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2760 is chloro difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2761 is chloro trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2762 is chloro trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2763 is chloro trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2764 is chloro trifluoromethyl cyclopropyl CH, Y3 is N X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2765 is chloro trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2766 is chloro trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2767 is chloro trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2768 is chloro trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2769 is chloro trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2770 is chloro trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2771 is chloro trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Br, X3 Y1 is CH, Y2 is
P.2772 is chloro trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2773 chloro 1 bromo CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2774 chloro 1 chloro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2775 chloro 1 cyano CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2776 chloro 1 cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2777 chloro 1 ethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2778 chloro 1 fluoro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2779 chloro 1 hydrogen CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2780 chloro 1 methoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2781 chloro 1 methyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2782 chloro 1 nitro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2783 chloro 1 trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2784 chloro 1 trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2785 chloro difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2786 chloro difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2787 chloro difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2788 chloro difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2789 chloro difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2790 chloro difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2791 chloro difluoromethyl hydrogen CH, Y3 is N
P.2792 X1 is chloro, X2 is C-F, X3 is difluoromethyl methoxy Y1 is CH, Y2 is chloro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2793 chloro difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2794 chloro difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2795 chloro difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2796 chloro difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2797 chloro trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2798 chloro trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2799 chloro trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2800 chloro trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2801 chloro trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2802 chloro trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2803 chloro trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2804 chloro trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2805 chloro trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2806 chloro trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2807 chloro trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2808 chloro trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2809 is chloro 1 bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2810 is chloro 1 chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2811 is chloro 1 cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2812 is chloro 1 cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2813 is chloro 1 ethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2814 is chloro 1 fluoro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2815 is chloro 1 hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2816 is chloro 1 methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2817 is chloro 1 methyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2818 is chloro 1 nitro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2819 is chloro 1 trifluoromethoxy CH, Y3 is N X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.2820 is chloro 1 trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2821 is chloro difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2822 is chloro difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2823 is chloro difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2824 is chloro difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2825 is chloro difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2826 is chloro difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2827 is chloro difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2828 is chloro difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2829 is chloro difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2830 is chloro difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2831 is chloro difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2832 is chloro difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2833 is chloro trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2834 is chloro trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2835 is chloro trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2836 is chloro trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2837 is chloro trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2838 is chloro trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2839 is chloro trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2840 is chloro trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2841 is chloro trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2842 is chloro trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2843 is chloro trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.2844 is chloro trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2845 chloro 1 bromo CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2846 chloro 1 chloro CH, Y3 is N
P.2847 X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy cyano Y1 is CH, Y2 is chloro 1 CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2848 chloro 1 cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2849 chloro 1 ethyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2850 chloro 1 fluoro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2851 chloro 1 hydrogen CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2852 chloro 1 methoxy CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2853 chloro 1 methyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2854 chloro 1 nitro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2855 chloro 1 trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2856 chloro 1 trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2857 chloro difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2858 chloro difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2859 chloro difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2860 chloro difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2861 chloro difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2862 chloro difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2863 chloro difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2864 chloro difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2865 chloro difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2866 chloro difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2867 chloro difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2868 chloro difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2869 chloro trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2870 chloro trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2871 chloro trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2872 chloro trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2873 chloro trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2874 chloro trifluoromethyl fluoro CH, Y3 is N X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2875 chloro trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2876 chloro trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2877 chloro trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2878 chloro trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2879 chloro trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-I, X3 is Y1 is CH, Y2 is
P.2880 chloro trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2881 fluoro 1 bromo CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2882 fluoro 1 chloro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2883 fluoro 1 cyano CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2884 fluoro 1 cyclopropyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2885 fluoro 1 ethyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2886 fluoro 1 fluoro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2887 fluoro 1 hydrogen CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2888 fluoro 1 methoxy CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2889 fluoro 1 methyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2890 fluoro 1 nitro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2891 fluoro 1 trifluoromethoxy CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2892 fluoro 1 trifluoromethyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2893 fluoro difluoromethyl bromo CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2894 fluoro difluoromethyl chloro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2895 fluoro difluoromethyl cyano CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2896 fluoro difluoromethyl cyclopropyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2897 fluoro difluoromethyl ethyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2898 fluoro difluoromethyl fluoro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2899 fluoro difluoromethyl hydrogen CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2900 fluoro difluoromethyl methoxy CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2901 fluoro difluoromethyl methyl CH, Y3 is N
P.2902 X1 is fluoro, X2 is C-F, X3 is difluoromethyl nitro Y1 is CH, Y2 is fluoro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2903 fluoro difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2904 fluoro difluoromethyl trifluoromethyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2905 fluoro trifluoromethyl bromo CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2906 fluoro trifluoromethyl chloro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2907 fluoro trifluoromethyl cyano CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2908 fluoro trifluoromethyl cyclopropyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2909 fluoro trifluoromethyl ethyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2910 fluoro trifluoromethyl fluoro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2911 fluoro trifluoromethyl hydrogen CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2912 fluoro trifluoromethyl methoxy CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2913 fluoro trifluoromethyl methyl CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2914 fluoro trifluoromethyl nitro CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2915 fluoro trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is fluoro, X2 is C-F, X3 is Y1 is CH, Y2 is
P.2916 fluoro trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2917 bromo 1 bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2918 bromo 1 chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2919 bromo 1 cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2920 bromo 1 cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2921 bromo 1 ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2922 bromo 1 fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2923 bromo 1 hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2924 bromo 1 methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2925 bromo 1 methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2926 bromo 1 nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2927 bromo 1 trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2928 bromo 1 trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2929 bromo difluoromethyl bromo CH, Y3 is N X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2930 bromo difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2931 bromo difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2932 bromo difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2933 bromo difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2934 bromo difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2935 bromo difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2936 bromo difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2937 bromo difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2938 bromo difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2939 bromo difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2940 bromo difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2941 bromo trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2942 bromo trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2943 bromo trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2944 bromo trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2945 bromo trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2946 bromo trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2947 bromo trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2948 bromo trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2949 bromo trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2950 bromo trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2951 bromo trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2952 bromo trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2953 bromo 1 bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2954 bromo 1 chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2955 bromo 1 cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2956 bromo 1 cyclopropyl CH, Y3 is N
P.2957 X1 is chloro, X2 is CH, X3 is chlorodifluoromethy ethyl Y1 is CH, Y2 is bromo 1 CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2958 bromo 1 fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2959 bromo 1 hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2960 bromo 1 methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y- is
P.2961 bromo 1 methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2962 bromo 1 nitro CH, Y3 is N
X1 is chloro, X2 is CH, Xs is chlorodifluoromethy Y1 is CH, Y2 is
P.2963 bromo 1 trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, Xs is chlorodifluoromethy Y1 is CH, Y2 is
P.2964 bromo 1 trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2965 bromo difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2966 bromo difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y- is
P.2967 bromo difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X* is Y1 is CH, Y2 is
P.2968 bromo difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is
P.2969 bromo difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2970 bromo difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2971 bromo difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2972 bromo difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X* is Y1 is CH, Y2 is
P.2973 bromo difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is
P.2974 bromo difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is
P.2975 bromo difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2976 bromo difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2977 bromo trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X* is Y1 is CH, Y- is
P.2978 bromo trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2979 bromo trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, Xs is Y1 is CH, Y2 is
P.2980 bromo trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2981 bromo trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2982 bromo trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2983 bromo trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X* is Y1 is CH, Y2 is
P.2984 bromo trifluoromethyl methoxy CH, Y3 is N X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2985 bromo trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2986 bromo trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2987 bromo trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.2988 bromo trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2989 bromo 1 bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2990 bromo 1 chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2991 bromo 1 cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2992 bromo 1 cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2993 bromo 1 ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2994 bromo 1 fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2995 bromo 1 hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2996 bromo 1 methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2997 bromo 1 methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2998 bromo 1 nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.2999 bromo 1 trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.3000 bromo 1 trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3001 bromo difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3002 bromo difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3003 bromo difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3004 bromo difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3005 bromo difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3006 bromo difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3007 bromo difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3008 bromo difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3009 bromo difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3010 bromo difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.301 1 bromo difluoromethyl trifluoromethoxy CH, Y3 is N
P.3012 X1 is chloro, X2 is CH, X3 is difluoromethyl trifluoromethyl Y1 is CH, Y2 is bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3013 bromo trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3014 bromo trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3015 bromo trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3016 bromo trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3017 bromo trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3018 bromo trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3019 bromo trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3020 bromo trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3021 bromo trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3022 bromo trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3023 bromo trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is CH, X3 is Y1 is CH, Y2 is
P.3024 bromo trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.3025 is trifluoromethyl 1 bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.3026 is trifluoromethyl 1 chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.3027 is trifluoromethyl 1 cyano CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.3028 is trifluoromethyl 1 cyclopropyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.3029 is trifluoromethyl 1 ethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.3030 is trifluoromethyl 1 fluoro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.3031 is trifluoromethyl 1 hydrogen CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.3032 is trifluoromethyl 1 methoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.3033 is trifluoromethyl 1 methyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.3034 is trifluoromethyl 1 nitro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.3035 is trifluoromethyl 1 trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 chlorodifluoromethy Y1 is CH, Y2 is
P.3036 is trifluoromethyl 1 trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.3037 is trifluoromethyl difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.3038 is trifluoromethyl difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is C-Cl, X3 Y1 is CH, Y2 is
P.3039 is trifluoromethyl difluoromethyl cyano CH, Y3 is N
Figure imgf000155_0001
CH, X3 is trifluoromethyl 1 CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3068 CH, X3 is trifluoromethyl 1 methoxy CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3069 CH, X3 is trifluoromethyl 1 methyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3070 CH, X3 is trifluoromethyl 1 nitro CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3071 CH, X3 is trifluoromethyl 1 trifluoromethoxy CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3072 CH, X3 is trifluoromethyl 1 trifluoromethyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3073 CH, X3 is trifluoromethyl difluoromethyl bromo CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3074 CH, X3 is trifluoromethyl difluoromethyl chloro CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3075 CH, X3 is trifluoromethyl difluoromethyl cyano CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3076 CH, X3 is trifluoromethyl difluoromethyl cyclopropyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3077 CH, X3 is trifluoromethyl difluoromethyl ethyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3078 CH, X3 is trifluoromethyl difluoromethyl fluoro CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3079 CH, X3 is trifluoromethyl difluoromethyl hydrogen CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3080 CH, X3 is trifluoromethyl difluoromethyl methoxy CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3081 CH, X3 is trifluoromethyl difluoromethyl methyl CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3082 CH, X3 is trifluoromethyl difluoromethyl nitro CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3083 CH, X3 is trifluoromethyl difluoromethyl trifluoromethoxy CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3084 CH, X3 is trifluoromethyl difluoromethyl trifluoromethyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3085 CH, X3 is trifluoromethyl trifluoromethyl bromo CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3086 CH, X3 is trifluoromethyl trifluoromethyl chloro CH, Y3 is N
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is
P.3087 CH, X3 is trifluoromethyl trifluoromethyl cyano CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3088 CH, X3 is trifluoromethyl trifluoromethyl cyclopropyl CH, Y3 is N
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is
P.3089 CH, X3 is trifluoromethyl trifluoromethyl ethyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3090 CH, X3 is trifluoromethyl trifluoromethyl fluoro CH, Y3 is N
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is
P.3091 CH, X3 is trifluoromethyl trifluoromethyl hydrogen CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3092 CH, X3 is trifluoromethyl trifluoromethyl methoxy CH, Y3 is N
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is
P.3093 CH, X3 is trifluoromethyl trifluoromethyl methyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3094 CH, X3 is trifluoromethyl trifluoromethyl nitro CH, Y3 is N X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is
P.3095 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethoxy CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3096 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethyl CH, Y3 is N
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3097 CH, X3 is trifluoromethyl 1 bromo CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3098 CH, X3 is trifluoromethyl 1 chloro CH, Y3 is N
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3099 CH, X3 is trifluoromethyl 1 cyano CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3100 CH, X3 is trifluoromethyl 1 cyclopropyl CH, Y3 is N
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3101 CH, X3 is trifluoromethyl 1 ethyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3102 CH, X3 is trifluoromethyl 1 fluoro CH, Y3 is N
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3103 CH, X3 is trifluoromethyl 1 hydrogen CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3104 CH, X3 is trifluoromethyl 1 methoxy CH, Y3 is N
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3105 CH, X3 is trifluoromethyl 1 methyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3106 CH, X3 is trifluoromethyl 1 nitro CH, Y3 is N
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3107 CH, X3 is trifluoromethyl 1 trifluoromethoxy CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3108 CH, X3 is trifluoromethyl 1 trifluoromethyl CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3109 CH, X3 is trifluoromethyl difluoromethyl bromo CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3110 CH, X3 is trifluoromethyl difluoromethyl chloro CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3111 CH, X3 is trifluoromethyl difluoromethyl cyano CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3112 CH, X3 is trifluoromethyl difluoromethyl cyclopropyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3113 CH, X3 is trifluoromethyl difluoromethyl ethyl CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3114 CH, X3 is trifluoromethyl difluoromethyl fluoro CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3115 CH, X3 is trifluoromethyl difluoromethyl hydrogen CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3116 CH, X3 is trifluoromethyl difluoromethyl methoxy CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3117 CH, X3 is trifluoromethyl difluoromethyl methyl CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3118 CH, X3 is trifluoromethyl difluoromethyl nitro CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3119 CH, X3 is trifluoromethyl difluoromethyl trifluoromethoxy CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3120 CH, X3 is trifluoromethyl difluoromethyl trifluoromethyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3121 CH, X3 is trifluoromethyl trifluoromethyl bromo CH, Y3 is N
P.3122 X1 is trifluoromethyl, X2 is trifluoromethyl chloro Y1 is CH, Y2 is CH, X3 is trifluoromethyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3123 CH, X3 is trifluoromethyl trifluoromethyl cyano CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3124 CH, X3 is trifluoromethyl trifluoromethyl cyclopropyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3125 CH, X3 is trifluoromethyl trifluoromethyl ethyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3126 CH, X3 is trifluoromethyl trifluoromethyl fluoro CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3127 CH, X3 is trifluoromethyl trifluoromethyl hydrogen CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3128 CH, X3 is trifluoromethyl trifluoromethyl methoxy CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3129 CH, X3 is trifluoromethyl trifluoromethyl methyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3130 CH, X3 is trifluoromethyl trifluoromethyl nitro CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3131 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethoxy CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3132 CH, X3 is trifluoromethyl trifluoromethyl trifluoromethyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3133 CH, X3 is hydrogen 1 bromo CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3134 CH, X3 is hydrogen 1 chloro CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3135 CH, X3 is hydrogen 1 cyano CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3136 CH, X3 is hydrogen 1 cyclopropyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3137 CH, X3 is hydrogen 1 ethyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3138 CH, X3 is hydrogen 1 fluoro CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3139 CH, X3 is hydrogen 1 hydrogen CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3140 CH, X3 is hydrogen 1 methoxy CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3141 CH, X3 is hydrogen 1 methyl CH, Y3 is N
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3142 CH, X3 is hydrogen 1 nitro CH, Y3 is N
X 1 is trifluoromethyl, X 1 is chlorodifluoromethy Y1 is CH, Y2 is
P.3143 CH, X3 is hydrogen 1 trifluoromethoxy CH, Y3 is N
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3144 CH, X3 is hydrogen 1 trifluoromethyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3145 CH, X3 is hydrogen difluoromethyl bromo CH, Y3 is N
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is
P.3146 CH, X3 is hydrogen difluoromethyl chloro CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3147 CH, X3 is hydrogen difluoromethyl cyano CH, Y3 is N
X1 is trifluoromethyl, X2 is Y1 is CH, Y2 is
P.3148 CH, X3 is hydrogen difluoromethyl cyclopropyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3149 CH, X3 is hydrogen difluoromethyl ethyl CH, Y3 is N
Figure imgf000159_0001
chloro 1 CH, Y3 is N
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.3178 chloro 1 nitro CH, Y3 is N
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.3179 chloro 1 trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is N, X3 is chlorodifluoromethy Y1 is CH, Y2 is
P.3180 chloro 1 trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3181 chloro difluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3182 chloro difluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3183 chloro difluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3184 chloro difluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3185 chloro difluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3186 chloro difluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3187 chloro difluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3188 chloro difluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3189 chloro difluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3190 chloro difluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3191 chloro difluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3192 chloro difluoromethyl trifluoromethyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3193 chloro trifluoromethyl bromo CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3194 chloro trifluoromethyl chloro CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3195 chloro trifluoromethyl cyano CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3196 chloro trifluoromethyl cyclopropyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3197 chloro trifluoromethyl ethyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3198 chloro trifluoromethyl fluoro CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3199 chloro trifluoromethyl hydrogen CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3200 chloro trifluoromethyl methoxy CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3201 chloro trifluoromethyl methyl CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3202 chloro trifluoromethyl nitro CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3203 chloro trifluoromethyl trifluoromethoxy CH, Y3 is N
X1 is chloro, X2 is N, X3 is Y1 is CH, Y2 is
P.3204 chloro trifluoromethyl trifluoromethyl CH, Y3 is N X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3205 N, X3 is trifluoromethyl 1 bromo CH, Y3 is N
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3206 N, X3 is trifluoromethyl 1 chloro CH, Y3 is N
X1 is trifluoromethyl, X2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3207 N, X3 is trifluoromethyl 1 cyano CH, Y3 is N
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3208 N, X3 is trifluoromethyl 1 cyclopropyl CH, Y3 is N
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3209 N, X3 is trifluoromethyl 1 ethyl CH, Y3 is N
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3210 N, X3 is trifluoromethyl 1 fluoro CH, Y3 is N
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3211 N, X3 is trifluoromethyl 1 hydrogen CH, Y3 is N
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3212 N, X3 is trifluoromethyl 1 methoxy CH, Y3 is N
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3213 N, X3 is trifluoromethyl 1 methyl CH, Y3 is N
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3214 N, X3 is trifluoromethyl 1 nitro CH, Y3 is N
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3215 N, X3 is trifluoromethyl 1 trifluoromethoxy CH, Y3 is N
X 1 is trifluoromethyl, X 2 is chlorodifluoromethy Y1 is CH, Y2 is
P.3216 N, X3 is trifluoromethyl 1 trifluoromethyl CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3217 N, X3 is trifluoromethyl difluoromethyl bromo CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3218 N, X3 is trifluoromethyl difluoromethyl chloro CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3219 N, X3 is trifluoromethyl difluoromethyl cyano CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3220 N, X3 is trifluoromethyl difluoromethyl cyclopropyl CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3221 N, X3 is trifluoromethyl difluoromethyl ethyl CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3222 N, X3 is trifluoromethyl difluoromethyl fluoro CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3223 N, X3 is trifluoromethyl difluoromethyl hydrogen CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3224 N, X3 is trifluoromethyl difluoromethyl methoxy CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3225 N, X3 is trifluoromethyl difluoromethyl methyl CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3226 N, X3 is trifluoromethyl difluoromethyl nitro CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3227 N, X3 is trifluoromethyl difluoromethyl trifluoromethoxy CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3228 N, X3 is trifluoromethyl difluoromethyl trifluoromethyl CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3229 N, X3 is trifluoromethyl trifluoromethyl bromo CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3230 N, X3 is trifluoromethyl trifluoromethyl chloro CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3231 N, X3 is trifluoromethyl trifluoromethyl cyano CH, Y3 is N
P.3232 X1 is trifluoromethyl, X2 is trifluoromethyl cyclopropyl Y1 is CH, Y2 is N, X3 is trifluoromethyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3233 N, X3 is trifluoromethyl trifluoromethyl ethyl CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3234 N, X3 is trifluoromethyl trifluoromethyl fluoro CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3235 N, X3 is trifluoromethyl trifluoromethyl hydrogen CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3236 N, X3 is trifluoromethyl trifluoromethyl methoxy CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3237 N, X3 is trifluoromethyl trifluoromethyl methyl CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3238 N, X3 is trifluoromethyl trifluoromethyl nitro CH, Y3 is N
X 1 is trifluoromethyl, X 2 is Y1 is CH, Y2 is
P.3239 N, X3 is trifluoromethyl trifluoromethyl trifluoromethoxy CH, Y3 is N
X 1 is trifluoromethyl, X 1 is Y1 is CH, Y2 is
P.3240 N, X3 is trifluoromethyl trifluoromethyl trifluoromethyl CH, Y3 is N
Figure imgf000162_0001
Table IP:
Table IP provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.OOl, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 2P:
Table 2P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.002, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 3P:
Table 3P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.003, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 4P:
Table 4P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.004, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 5P:
Table 5P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.005, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 6P:
Table 6P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.006, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 7P:
Table 7P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.007, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 8P:
Table 8P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.008, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P. Table 9P:
Table 9P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.009, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 10P:
Table 10P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.010, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table I IP:
Table 1 IP provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.011, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 12P:
Table 12P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.012, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 13P:
Table 13P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.013, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 14P:
Table 14P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.014, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 15P:
Table 15P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.015, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 16P:
Table 16P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.016, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 17P:
Table 17P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.017, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 18P:
Table 18P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.018, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 19P:
Table 19P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.019, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 20P:
Table 20P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.020, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 2 IP:
Table 21P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.021, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 22P:
Table 22P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.022, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 23P:
Table 23P provides 3240 compounds of fonnula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.023, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 24P:
Table 24P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.024, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 25P:
Table 25P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.025, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 26P:
Table 26P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.026, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P. Λ
- 162 -
Table 27P:
Table 27P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.027, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 28P:
Table 28P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.028, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 29P:
Table 29P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.029, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 30P:
Table 30P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.030, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 3 IP:
Table 3 IP provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.031 , X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 32P:
Table 32P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.032, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 33P:
Table 33P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.033, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 34P:
Table 34P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.034, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 35P:
Table 35P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.035, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 36P:
Table 36P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.036, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 37P:
Table 37P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.037, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 38P:
Table 38P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.038, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 39P:
Table 39P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.039, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 40P:
Table 40P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.040, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 4 IP:
Table 41P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.041 , X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 42P:
Table 42P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.042, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 43P:
Table 43P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.043, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 44P:
Table 44P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.044, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P. Λ r~
- 163 -
Table 45P:
Table 45P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.045, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 46P:
Table 46P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.046, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 47P:
Table 47P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.047, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 48P:
Table 48P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.048, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 49P:
Table 49P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.049, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 50P:
Table 50P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.050, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 5 IP:
Table 51P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.051, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 52P:
Table 52P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.052, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 53P:
Table 53P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.053, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 54P:
Table 54P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.054, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 55P:
Table 55P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.055, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 56P:
Table 56P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.056, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 57P:
Table 57P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.057, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 58P:
Table 58P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.058, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 59P:
Table 59P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.059, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 60P:
Table 60P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.060, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 6 IP:
Table 61P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.061, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 62P:
Table 62P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.062, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P. Λ , .
- 164 -
Table 63Ρ:
Table 63P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.063, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 64P:
Table 64P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.064, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 65P:
Table 65P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.065, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 66P:
Table 66P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.066, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 67P:
Table 67P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.067, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 68P:
Table 68P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.068, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 69P:
Table 69P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.069, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 70P:
Table 70P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.070, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 7 IP:
Table 71P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.071, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 72P:
Table 72P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.072, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 73P:
Table 73P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.073, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 74P:
Table 74P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.074, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 75P:
Table 75P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.075, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 76P:
Table 76P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.076, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 77P:
Table 77P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.077, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 78P:
Table 78P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.078, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 79P:
Table 79P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.079, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 80P:
Table 80P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.080, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P. Λ r
- 165 -
Table 8 IP:
Table 81P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.081 , X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 82P:
Table 82P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.082, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 83P:
Table 83P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.083, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 84P:
Table 84P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.084, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 85P:
Table 85P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.085, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 86P:
Table 86P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.086, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 87P:
Table 87P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.087, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 88P:
Table 88P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.088, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 89P:
Table 89P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.089, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 90P:
Table 90P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.090, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 91P
Table 91P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.091, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 92P
Table 92P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.092, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 93P
Table 93P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.093, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 94P
Table 94P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.094, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 95P
Table 95P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.095, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 96P
Table 96P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.096, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 97P
Table 97P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.097, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 98P
Table 98P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.098, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 99P , rr
- 166 -
Table 99P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.099, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 100P
Table 100P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.100, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 101P
Table 101P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.101, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 102P
Table 102P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.102, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 103P
Table 103P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.103, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 104P
Table 104P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.104, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 105P
Table 105P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.105, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 106P
Table 106P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.106, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 107P
Table 107P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.107, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 108P
Table 108P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.108, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 109P
Table 109P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.109, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table H OP
Table HOP provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.110, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 11 IP:
Table 11 IP provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.111 , X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 1 12 P
Table 112P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.112, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 113 P
Table 113P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.113, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 1 14 P
Table 1 14P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, Rl is hydrogen, R2 is G.114, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 115 P
Table 115P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.115, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 116 P
Table 1 16P provides 3240 compounds of formula (I-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.116, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Figure imgf000169_0001
Table 17 P
Table 17P provides 3240 compounds of formula (II- A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.001 X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 18 P
Table 18P provides 3240 compounds of fonnula (II-A) wherein G is oxygen, R is hydrogen, R is G.002 X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 19 P
Table 19P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.003 X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 20 P
Table 20P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.004 X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 21 P
Table 21P provides 3240 compounds of fonnula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.005 X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 22 P
Table 22P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.006 X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 23 P
Table 23P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.007 X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 24 P
Table 24P provides 3240 compounds of fonnula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.008 X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 25 P
Table 25P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.009 X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 26 P
Table 26P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.010 X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 27 P
Table 27P provides 3240 compounds of fonnula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.01 1 X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 28 P
Table 28P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.012 X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 29 P
Table 29P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.013 X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 30 P
Table 30P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.014 X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 31 P
Table 13 IP provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.015, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 132 P ,„
- 168 -
Table 132P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.016, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 133 P
Table 133P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.017, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 134 P
Table 134P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.018, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 135 P
Table 135P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.019, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 136 P
Table 136P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.020, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 137 P
Table 137P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.021, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 138 P
Table 138P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.022, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 139 P
Table 139P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.023, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 140 P
Table 140P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.024, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 141 P
Table 141P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.025, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 142 P
Table 142P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.026, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 143 P
Table 143P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.027, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 144 P
Table 144P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.028, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 145 P
Table 145P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.029, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 146 P
Table 146P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.030, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 147 P
Table 147P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.031, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 148 P
Table 148P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.032, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 149 P
Table 149P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.033, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 150 P
Table 150P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.034, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P. 1 ,„
- 169 -
Table 151 P
Table 15 IP provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.035, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 152 P
Table 152P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.036, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 153 P
Table 153P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.037, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 154 P
Table 154P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.038, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 155 P
Table 155P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.039, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 156 P
Table 156P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.040, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 157 P
Table 157P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.041, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 158 P
Table 158P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.042, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 159 P
Table 159P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.043, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 160 P
Table 160P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.044, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 161 P
Table 161P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.045, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 162 P
Table 162P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.046, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 163 P
Table 163P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.047, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 164 P
Table 164P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R' is G.048, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 165 P
Table 165P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.049, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 166 P
Table 166P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.050, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 167 P
Table 167P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.051, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 168 P
Table 168P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.052, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 169 P Table 169P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.053, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 170 P
Table 170P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.054, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 171 P
Table 171P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.055, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 172 P
Table 172P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.056, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 173 P
Table 173P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.057, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 174 P
Table 174P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.058, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 175 P
Table 175P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.059, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 176 P
Table 176P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.060, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 177 P
Table 177P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.061, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 178 P
Table 178P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.062, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 179 P
Table 179P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.063, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 180 P
Table 180P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.064, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 181 P
Table 18 IP provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.065, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 182 P
Table 182P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.066, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 183 P
Table 183P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.067, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 184 P
Table 184P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.068, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 185 P
Table 185P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.069, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 186 P
Table 186P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.070, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 187 P
Table 187P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.071, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P. Table 188 P
Table 188P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.072, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 189 P
Table 189P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.073, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 190 P
Table 190P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R~ is G.074, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 191 P
Table 191P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.075, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 192 P
Table 192P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.076, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 193 P
Table 193P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.077, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 194 P
Table 194P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.078, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 195 P
Table 195P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.079, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 196 P
Table 196P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.080, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 197 P
Table 197P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.081 , X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 198 P
Table 198P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.082, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 199 P
Table 199P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.083, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 200 P
Table 200P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.084, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 201 P
Table 201P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.085, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 202 P
Table 202P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.086, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 203 P
Table 203P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen R2 is G.087, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 204 P
Table 204P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.088, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 205 P
Table 205P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.089, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 206 P Table 206P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen R2 is G.090, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 207 P
Table 207P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.091, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 208 P
Table 208P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.092, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 209 P
Table 209P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.093, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 210 P
Table 21 OP provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.094, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 211 P
Table 21 IP provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.095, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 212 P
Table 212P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.096, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 213 P
Table 213P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.097, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 214 P
Table 214P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.098, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 215 P
Table 215P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.099, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 216 P
Table 216P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.100, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 217 P
Table 217P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.101, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 218 P
Table 218P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.102, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 219 P
Table 219P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.103, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 220 P
Table 220P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.104, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 221 P
Table 22 IP provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.105, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 222 P
Table 222P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.106, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 223 P
Table 223P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.107, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 224 P
Table 224P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.108, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P. Table 225 P
Table 225P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.109, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 226 P
Table 226P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.110, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 227 P
Table 227P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 11, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 228 P
Table 228P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.112, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 229 P
Table 229P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G.113, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 230 P
Table 230P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 14, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 231 P
Table 23 IP provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 15, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Table 232 P
Table 232P provides 3240 compounds of formula (II-A) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 16, X1, X2, X3, Y1, Y2, Y3, X4 and R5 have the values listed in the table P.
Figure imgf000175_0001
Q.020 X1 is chloro, X2 is C-Cl, X3 is chloro difluoromethyl
Q.021 X1 is chloro, X2 is C-Cl, X3 is chloro trifluoromethyl
Q.022 X1 is chloro, X2 is C-I, X3 is chloro chlorodifluoromethyl
Q.023 X1 is chloro, X2 is C-I, X3 is chloro difluoromethyl
Q.024 X1 is chloro, X2 is C-I, X3 is chloro trifluoromethyl
Q.025 X1 is fluoro, X2 is C-F, X3 is fluoro chlorodifluoromethyl
Q.026 X1 is fluoro, X2 is C-F, X3 is fluoro difluoromethyl
Q.027 X1 is fluoro, X2 is C-F, X3 is fluoro trifluoromethyl
Q.028 X1 is chloro, X2 is CH, X3 is bromo chlorodifluoromethyl
Q.029 X1 is chloro, X2 is CH, X3 is bromo difluoromethyl
Q.030 X1 is chloro, X2 is CH, X3 is bromo trifluoromethyl
Q.031 X1 is chloro, X2 is CH, X3 is bromo chlorodifluoromethyl
Q.032 X1 is chloro, X2 is CH, X3 is bromo difluoromethyl
Q.033 X1 is chloro, X2 is CH, X3 is bromo trifluoromethyl
Q.034 X1 is chloro, X2 is CH, X3 is bromo chlorodifluoromethyl
Q.035 X1 is chloro, X2 is CH, X3 is bromo difluoromethyl
Q.036 X1 is chloro, X2 is CH, X3 is bromo trifluoromethyl
Q.037 X1 is chloro, X2 is C-Cl, X3 is trifluoromethyl chlorodifluoromethyl
Q.038 X1 is chloro, X2 is C-Cl, X3 is trifluoromethyl difluoromethyl
Q.039 X1 is chloro, X2 is C-Cl, X3 is trifluoromethyl trifluoromethyl
Q.040 X1 is trifluoromethyl, X2 is CH, X3 is trifluoromethyl chlorodifluoromethyl
Q.041 X1 is trifluoromethyl, X2 is CH, X3 is trifluoromethyl difluoromethyl
Q.042 X1 is trifluoromethyl, X2 is CH, X3 is trifluoromethyl trifluoromethyl
Q.043 X1 is trifluoromethyl, X2 is CH, X3 is trifluoromethyl chlorodifluoromethyl
Q.044 X1 is trifluoromethyl, X2 is CH, X3 is trifluoromethyl difluoromethyl
Q.045 X1 is trifluoromethyl, X2 is CH, X3 is trifluoromethyl trifluoromethyl
Q.046 X1 is trifluoromethyl, X2 is CH, X3 is hydrogen chlorodifluoromethyl
Q.047 X1 is trifluoromethyl, X2 is CH, X3 is hydrogen difluoromethyl
Q.048 X1 is trifluoromethyl, X2 is CH, X3 is hydrogen trifluoromethyl
Q.049 X1 is chloro, X2 is N, X3 is chloro chlorodifluoromethyl
Q.050 X1 is chloro, X2 is N, X3 is chloro difluoromethyl
Q.051 X1 is chloro, X2 is N, X3 is chloro trifluoromethyl
Q.052 X1 is trifluoromethyl, X2 is N, X3 is trifluoromethyl chlorodifluoromethyl
Q.053 X1 is trifluoromethyl, X2 is N, X3 is trifluoromethyl difluoromethyl
Q.054 X1 is trifluoromethyl, X2 is N, X3 is trifluoromethyl trifluoromethyl Λ„Γ
Figure imgf000177_0001
Table 10:
Table 1 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.001, X1, X2, X3and X4 have the values listed in the table Q.
Table 20:
Table 2 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.002, X1, X2, X3and X4 have the values listed in the table Q.
Table 30:
Table 3 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.003, X1, X2, X3and X4 have the values listed in the table Q.
Table 40:
Table 4 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.004, X1, X2, X3and X4 have the values listed in the table Q.
Table 50:
Table 5 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.005, X1, X2, X3and X4 have the values listed in the table Q.
Table 60:
Table 6 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.006, X1, X2, X3and X4 have the values listed in the table Q.
Table 70:
Table 7 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.007, X1, X2, X3and X4 have the values listed in the table Q.
Table 80:
Table 8 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.008, X1, X2, X3and X4 have the values listed in the table Q.
Table 90:
Table 9 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.009, X1, X2, X3and X4 have the values listed in the table Q.
Table lOQ:
Table 10 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.OlO, X1, X2, X3and X4 have the values listed in the table Q.
Table 110:
Table H Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.011, X1, X2, X3and X4 have the values listed in the table Q.
Table 120:
Table 12 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.012, X1, X2, X3and X4 have the values listed in the table Q.
Table 130:
Table 13 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.013, X1, X2, X3and X4 have the values listed in the table Q.
Table 140:
Table 14 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.014, X1, X2, X3and X4 have the values listed in the table Q.
Table 150:
Table 15 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.015, X1, X2, X3and X4 have the values listed in the table Q. Table 160:
Table 16 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.016, X1, X2, X3and X4 have the values listed in the table Q.
Table 170:
Table 17 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.017, X1, X2, X3and X4 have the values listed in the table Q.
Table 180:
Table 18 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.018, X1, X2, X3and X4 have the values listed in the table Q.
Table 190:
Table 19 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.019, X1, X2, X3and X4 have the values listed in the table Q.
Table 200
Table 20 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.020, X1, X2, X3and X4 have the values listed in the table Q.
Table 210:
TTaabbllee 2211 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.021, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 220:
TTaabbllee 2222 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.022, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 230:
TTaabbllee 2233 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.023, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 240:
TTaabbllee 2244 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.024, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 250:
TTaabbllee 2255 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.025, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 260:
TTaabbllee 2266 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.026, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 270:
TTaabbllee 2277 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.027, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 280:
TTaabbllee 2288 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.028, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 290:
TTaabbllee 2299 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.029, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 300:
TTaabbllee 3300 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.030, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 310:
TTaabbllee 3311 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.031, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 320:
TTaabbllee 3322 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.032, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 330:
Table 33 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.033, X1, X2, X3and X4 have the values listed in the table Q. Table 340:
Table 34 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.034, X1, X2, X3and X4 have the values listed in the table Q.
Table 350:
Table 35 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.035, X1, X2, X3and X4 have the values listed in the table Q.
Table 360:
Table 36 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.036, X1, X2, X3and X4 have the values listed in the table Q.
Table 370:
Table 37 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.037, X1, X2, X3and X4 have the values listed in the table Q.
Table 380:
TTaabbllee 3388 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.038, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 390:
TTaabbllee 3399 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.039, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 400:
TTaabbllee 4400 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.040, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 410:
TTaabbllee 4411 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.041, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 420:
TTaabbllee 4422 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.042, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 430:
TTaabbllee 4433 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.043, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 440:
TTaabbllee 4444 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.044, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 450:
TTaabbllee 4455 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.045, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 460:
TTaabbllee 4466 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.046, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 470:
TTaabbllee 4477 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.047, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 480:
TTaabbllee 4488 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.048, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 490:
TTaabbllee 4499 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.049, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 500:
TTaabbllee 5500 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.050, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 510:
Table 51 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.051, X1, X2, X3and X4 have the values listed in the table Q. Table 520:
Table 52 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.052, X1, X2, X3and X4 have the values listed in the table Q.
Table 530:
Table 53 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.053, X1, X2, X3and X4 have the values listed in the table Q.
Table 540:
Table 54 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.054, X1, X2, X3and X4 have the values listed in the table Q.
Table 550:
Table 55 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.055, X1, X2, X3and X4 have the values listed in the table Q.
Table 560:
Table 56 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.056, X1, X2, X3and X4 have the values listed in the table Q.
Table 570:
TTaabbllee 5577 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.057, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 580:
TTaabbllee 5588 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.058, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 590:
TTaabbllee 5599 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.059, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 600:
TTaabbllee 6600 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.060, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 610:
TTaabbllee 6611 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.061, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 620:
TTaabbllee 6622 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.062, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 630:
TTaabbllee 6633 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.063, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 640:
TTaabbllee 6644 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.064, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 650:
TTaabbllee 6655 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.065, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 660:
TTaabbllee 6666 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.066, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 670:
TTaabbllee 6677 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.067, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 680:
TTaabbllee 6688 QQ provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.068, XX11,, XX22,, XX33aand X4 have the values listed in the table Q.
Table 690:
Table 69 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.069, X1, X2, X3and X4 have the values listed in the table Q. Table 70O:
Table 70 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.070, X1, X2, X3and X4 have the values listed in the table Q.
Table 710:
Table 71 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.071, X1, X2, X3and X4 have the values listed in the table Q.
Table 720:
Table 72 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.072, X1, X2, X3and X4 have the values listed in the table Q.
Table 730:
Table 73 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.073, X1, X2, X3and X4 have the values listed in the table Q.
Table 740:
Table 74 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.074, X1, X2, X3and X4 have the values listed in the table Q.
Table 750:
Table 75 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.075, X1, X2, X3and X4 have the values listed in the table Q.
Table 760:
Table 76 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.076, X1, X2, X3and X4 have the values listed in the table Q.
Table 770:
Table 77 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.077, X1, X2, X3and X4 have the values listed in the table Q.
Table 780:
Table 78 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.078, X1, X2, X3and X4 have the values listed in the table Q.
Table 790:
Table 79 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.079, X1, X2, X3and X4 have the values listed in the table Q.
Table 800:
Table 80 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.080, X1, X2, X3and X4 have the values listed in the table Q.
Table 810:
Table 81 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.081, X1, X2, X3and X4 have the values listed in the table Q.
Table 820:
Table 82 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.082, X1, X2, X3and X4 have the values listed in the table Q.
Table 830:
Table 83 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.083, X1, X2, X3and X4 have the values listed in the table Q.
Table 840:
Table 84 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.084, X1, X2, X3and X4 have the values listed in the table Q.
Table 850:
Table 85 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.085, X1, X2, X3and X4 have the values listed in the table Q.
Table 860:
Table 86 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.086, X1, X2, X3and X4 have the values listed in the table Q.
Table 870:
Table 87 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.087, X1, X2, X3and X4 have the values listed in the table Q. ΟΛ
- l oU -
Table 880:
Table 88 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.088, X1, X2, X3and X4 have the values listed in the table Q.
Table 890:
Table 89 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.089, X1, X2, X3and X4 have the values listed in the table Q.
Table 900:
Table 90 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.090, X1, X2, X3and X4 have the values listed in the table Q.
Table 910:
Table 91 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.091, X1, X2, X3and X4 have the values listed in the table Q.
Table 92 O:
Table 92 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.092, X1, X2, X3and X4 have the values listed in the table Q.
Table 93 0:
Table 93 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.093, X1, X2, X3and X4 have the values listed in the table Q.
Table 94
Table 94 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.094, X1, X2, X3and X4 have the values listed in the table Q.
Table 95 0:
Table 95 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.095, X1, X2, X3and X4 have the values listed in the table Q.
Table 96 0:
Table 96 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.096, X1, X2, X3and X4 have the values listed in the table Q.
Table 97 0:
Table 97 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.097, X1, X2, X3and X4 have the values listed in the table Q.
Table 98 0:
Table 98 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.098, X1, X2, X3and X4 have the values listed in the table Q.
Table 99 0:
Table 99 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.099, X1, X2, X3and X4 have the values listed in the table Q.
Table 100 0:
Table 100 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.100, X1, X2, X3and X4 have the values listed in the table Q.
Table 101 0:
Table 101 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.101, X1, X2, X3and X4 have the values listed in the table Q.
Table 102 O:
Table 102 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.102, X1, X2, X3and X4 have the values listed in the table Q.
Table 103 O:
Table 103 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.103, X1, X2, X3and X4 have the values listed in the table Q.
Table 104 O:
Table 104 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.104, X1, X2, X3and X4 have the values listed in the table Q.
Table 105 O:
Table 105 Q provides 54 compounds of formula (I-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.105, X1, X2, X3and X4 have the values listed in the table Q.
Table 106 O: Table 106 Q provides 54 compounds of formula ( B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.106, X1, X2, X3and X4 have the values listed in the tab e O.
Table 07 O:
Table 07 Q provides 54 compounds of formula ( -B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.107, χ', χ2 X3and X4 have the values listed in the tab e O.
Table 08 O:
Table 08 Q provides 54 compounds of formula ( -B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.108, χ', χ2 X3and X4 have the values listed in the tab e O.
Table 09 O:
Table 09 Q provides 54 compounds of formula ( -B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.109, χ', χ2 X3and X4 have the values listed in the tab e O.
Table 0_Qi
Table 0 Q provides 54 compounds of formula ( -B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.110,
X1, X: X3and X4 have the values listed in the tab e O.
Table IQi
Table 1 Q provides 54 compounds of formula ( -B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.111 ,
X1, X: X3and X4 have the values listed in the tab e O.
Table 2Q
Table 2 Q provides 54 compounds of formula ( -B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.112,
X1, X: X3and X4 have the values listed in the tab e O.
Table 3_Qi
Table 3 Q provides 54 compounds of formula ( -B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.113,
X1, X: X3and X4 have the values listed in the tab e O.
Table 4_Qi
Table 4 Q provides 54 compounds of formula ( -B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.114,
X1, X: X3and X4 have the values listed in the tab e O.
Table 5_Ql
Table 5 Q provides 54 compounds of formula ( -B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.115,
X1, X: X3and X4 have the values listed in the tab e O.
Table 6_Ql
Table 116 Q provides 54 compounds of formula ( -B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.116, X1, X2, X3and X4 have the values listed in the tab e O.
Figure imgf000183_0001
Table 117 0:
Table 117 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.001, X1, X2, X3 and X4 have the values listed in the table Q.
Table 118 O:
Table 118 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.002, X1, X2, X3and X4 have the values listed in the table Q.
Table 119 0:
Table 119 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.003, X1, X2, X3and X4 have the values listed in the table Q.
Table 120 O:
Table 120 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.004, X1, X2, X3and X4 have the values listed in the table Q.
Table 121 0: Table 121 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.005, X1, X2, X3and X4 have the values listed in the table Q.
Table 22 0:
Table 22 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.006,
X1, X: X3and X4 have the values listed in the table Q.
Table 23 O:
Table 23 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.007,
X1, X: X3and X4 have the values listed in the table Q.
Table 24 0:
Table 24 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.008,
X1, X: X3and X4 have the values listed in the table Q.
Table 25 0:
Table 25 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.009,
X1, X: X3and X4 have the values listed in the table Q.
Table 26 0:
Table 26 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.010,
X1, X: X3and X4 have the values listed in the table Q.
Table 27 0:
Table 27 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.011,
X1, X: X3and X4 have the values listed in the table Q.
Table 28 0:
Table 28 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.012,
X1, X: X3and X4 have the values listed in the table Q.
Table 29 0:
Table 29 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.013,
X1, X: X3and X4 have the values listed in the table Q.
Table 30 O:
Table 30 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.014,
X1, X: X3and X4 have the values listed in the table Q.
Table 31 O:
Table 31 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.015,
X1, X: X3and X4 have the values listed in the table Q.
Table 32 0:
Table 32 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.016,
X1, X: X3and X4 have the values listed in the table Q.
Table 33 O:
Table 33 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.017,
X1, X: X3and X4 have the values listed in the table Q.
Table 34 0:
Table 34 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.018,
X1, X: X3and X4 have the values listed in the table Q.
Table 35 0:
Table 35 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.019,
X1, X: X3and X4 have the values listed in the table Q.
Table 36 0:
Table 36 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.020,
X1, X: X3and X4 have the values listed in the table Q.
Table 37 0:
Table 37 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.021,
X1, X: X3and X4 have the values listed in the table Q.
Table 38 0:
Table 38 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.022,
X1, X: X3and X4 have the values listed in the table Q.
Table 39 0:
Table 39 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.023, X1, X2, X3and X4 have the values listed in the table Q. Table 40 0:
Table 40 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.024,
X1, X: X3and X4 have the values listed in the table Q.
Table 41 O:
Table 41 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.025, X1, X: X3and X4 have the values listed in the table Q.
Table 42 0:
Table 42 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.026,
X1, X: X3and X4 have the values listed in the table Q.
Table 43 O:
Table 43 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.027,
X1, X: X3and X4 have the values listed in the table Q.
Table 44 0:
Table 44 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.028,
X1, X: X3and X4 have the values listed in the table Q,
Table 45 0:
Table 45 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.029,
X1, X: X3and X4 have the values listed in the table Q.
Table 46 0:
Table 46 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.030, χ', χ2 X3and X4 have the values listed in the table Q.
Table 47 0:
Table 47 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.031, χ', χ2 X3and X4 have the values listed in the table Q,
Table 48 0:
Table 48 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.032, χ', χ2 X3and X4 have the values listed in the table Q.
Table 49 0:
Table 49 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.033, χ', χ2 X3and X4 have the values listed in the table Q.
Table 50 0:
Table 50 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.034,
X1, X: X3and X4 have the values listed in the table Q,
Table 51 0:
Table 51 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.035, χ', χ2 X3and X4 have the values listed in the table Q.
Table 52 0:
Table 52 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.036, χ', χ2 X3and X4 have the values listed in the table Q.
Table 53 0:
Table 53 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.037, χ', χ2 X3and X4 have the values listed in the table Q.
Table 54 0:
Table 54 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.038, χ', χ2 X3and X4 have the values listed in the table Q.
Table 55 O:
Table 55 Q provides 54 compounds of formula (ITB) wherein G is oxygen, R1 is hydrogen, R2 is G.039, χ', χ2 X3and X4 have the values listed in the table Q.
Table 56 0:
Table 56 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.040, χ', χ2 X3and X4 have the values listed in the table Q,
Table 57 0:
Table 157 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.041, X1, X2, X3and X4 have the values listed in the table Q.
Table 158 O: Table 158 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.042, X1, X2, X3and X4 have the values listed in the table Q.
Table 59 0:
Table 59 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.043, χ', χ2 X3and X4 have the values listed in the table Q.
Table 60 O:
Table 60 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.044, χ', χ2 X3and X4 have the values listed in the table Q.
Table 61 O:
Table 61 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.045, χ', χ2 X3and X4 have the values listed in the table Q.
Table 62 0:
Table 62 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.046,
X1, X: X3and X4 have the values listed in the table Q.
Table 63 0:
Table 63 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.047,
X1, X: X3and X4 have the values listed in the table Q.
Table 64 0:
Table 64 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.048,
X1, X: X3and X4 have the values listed in the table Q.
Table 65 0:
Table 65 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.049,
X1, X: X3and X4 have the values listed in the table Q.
Table 66 0:
Table 66 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.050,
X1, X: X3and X4 have the values listed in the table Q.
Table 67 0:
Table 67 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.051,
X1, X: X3and X4 have the values listed in the table Q.
Table 68 0:
Table 68 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.052,
X1, X: X3and X4 have the values listed in the table Q.
Table 69 0:
Table 69 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.053,
X1, X: X3and X4 have the values listed in the table Q.
Table 70 O:
Table 70 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.054,
X1, X: X3and X4 have the values listed in the table Q.
Table 71 O:
Table 71 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.055,
X1, X: X3and X4 have the values listed in the table Q.
Table 72 0:
Table 72 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.056,
X1, X: X3and X4 have the values listed in the table Q.
Table 73 O:
Table 73 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.057,
X1, X: X3and X4 have the values listed in the table Q.
Table 74 0:
Table 74 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.058,
X1, X: X3and X4 have the values listed in the table Q.
Table 75 0:
Table 75 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.059, χ', χ2 X3and X4 have the values listed in the table Q.
Table 76 0:
Table 76 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.060, X1, X2, X3and X4 have the values listed in the table Q. Table 77 0:
Table 77 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.061,
X1, X: X3and X4 have the values listed in the table Q.
Table 78 0:
Table 78 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.062, X1, X: X3and X4 have the values listed in the table Q.
Table 79 0:
Table 79 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.063,
X1, X: X3and X4 have the values listed in the table Q.
Table 80 O:
Table 80 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.064,
X1, X: X3and X4 have the values listed in the table Q.
Table 81 O:
Table 81 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.065,
X1, X: X3and X4 have the values listed in the table Q.
Table 82 0:
Table 82 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.066,
X1, X: X3and X4 have the values listed in the table Q.
Table 83 0:
Table 83 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.067, χ', χ2 X3and X4 have the values listed in the table Q.
Table 84 0:
Table 84 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.068, χ', χ2 X3and X4 have the values listed in the table Q,
Table 85 0:
Table 85 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.069, χ', χ2 X3and X4 have the values listed in the table Q.
Table 86 0:
Table 86 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.070, χ', χ2 X3and X4 have the values listed in the table Q.
Table 87 0:
Table 87 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.071,
X1, X: X3and X4 have the values listed in the table Q,
Table 88 0:
Table 88 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.072, χ', χ2 X3and X4 have the values listed in the table Q.
Table 89 0:
Table 89 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.073, χ', χ2 X3and X4 have the values listed in the table Q.
Table 90 0:
Table 90 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.074, χ', χ2 X3and X4 have the values listed in the table Q.
Table 91 O:
Table 91 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.075, χ', χ2 X3and X4 have the values listed in the table Q.
Table 92 0:
Table 92 Q provides 54 compounds of formula (ITB) wherein G is oxygen, R1 is hydrogen, R2 is G.076, χ', χ2 X3and X4 have the values listed in the table Q.
Table 93 O:
Table 93 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R1 is hydrogen, R2 is G.077, χ', χ2 X3and X4 have the values listed in the table Q,
Table 94 0:
Table 194 Q provides 54 compounds of formula (II-B) wherein G is oxygen, R is hydrogen, R is G.078, X1, X2, X3and X4 have the values listed in the table Q.
Table 195 O: 1 fl ,
- l oo -
Table 195 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.079, X1, X2, X3and X4 have the values listed in the table Q.
Table 196 0:
Table 196 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.080, X1, X2, X3and X4 have the values listed in the table Q.
Table 197 0:
Table 197 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.081, X1, X2, X3and X4 have the values listed in the table Q.
Table 198 0:
Table 198 Q provides 54 compounds of formula (ITB) wherein G1 is oxygen, R1 is hydrogen, R2 is G.082, X1, X2, X3and X4 have the values listed in the table Q.
Table 199 0:
Table 199 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.083, X1, X2, X3and X4 have the values listed in the table Q.
Table 200 0:
Table 200 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.084, X1, X2, X3and X4 have the values listed in the table Q.
Table 201 0:
Table 201 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.085, X1, X2, X3and X4 have the values listed in the table Q.
Table 202 O:
Table 202 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.086, X1, X2, X3and X4 have the values listed in the table Q.
Table 203 O:
Table 203 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen R2 is G.087, X1, X2, X3and X4 have the values listed in the table Q.
Table 204 O:
Table 204 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.088, X1, X2, X3and X4 have the values listed in the table Q.
Table 205 O:
Table 205 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.089, X1, X2, X3and X4 have the values listed in the table Q.
Table 206 0:
Table 206 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen R2 is G.090, X1, X2, X3and X4 have the values listed in the table Q.
Table 207 O:
Table 207 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.091, X1, X2, X3and X4 have the values listed in the table Q.
Table 208 O:
Table 208 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.092, X1, X2, X3and X4 have the values listed in the table Q.
Table 209 O:
Table 209 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.093, X1, X2, X3and X4 have the values listed in the table Q.
Table 210 O:
Table 210 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.094, X1, X2, X3and X4 have the values listed in the table Q.
Table 211 O:
Table 211 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.095, X1, X2, X3and X4 have the values listed in the table Q.
Table 212 O:
Table 212 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.096, X1, X2, X3and X4 have the values listed in the table Q.
Table 213 O:
Table 213 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.097, X1, X2, X3and X4 have the values listed in the table Q. - I o / -
Table 214 0:
Table 214 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.098, X1, X2, X3and X4 have the values listed in the table Q.
Table 215 O:
Table 215 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.099, X1, X2, X3and X4 have the values listed in the table Q.
Table 216 0:
Table 216 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 00, X1, X2, X3and X4 have the values listed in the table Q.
Table 217 0:
Table 217 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 01, X1, X2, X3and X4 have the values listed in the table Q.
Table 218 O:
Table 218 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 02, X1, X2, X3and X4 have the values listed in the table Q.
Table 219 0:
Table 219 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 03, X1, X2, X3and X4 have the values listed in the table Q.
Table 220 0:
Table 220 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.104, X1, X2, X3and X4 have the values listed in the table Q.
Table 221 0:
Table 221 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 05, X1, X2, X3and X4 have the values listed in the table Q.
Table 222 Q:
Table 222 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.106, X1, X2, X3and X4 have the values listed in the table Q.
Table 223 0:
Table 223 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.107, X1, X2, X3and X4 have the values listed in the table Q.
Table 224 0:
Table 224 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 08, X1, X2, X3and X4 have the values listed in the table Q.
Table 225 0:
Table 225 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.109, X1, X2, X3and X4 have the values listed in the table Q.
Table 226 0:
Table 226 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.110, X1, X2, X3and X4 have the values listed in the table Q.
Table 227 0:
Table 227 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.111 , X1, X2, X3and X4 have the values listed in the table Q.
Table 228 O:
Table 228 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.112, X1, X2, X3and X4 have the values listed in the table Q.
Table 229 O:
Table 229 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 13, X1, X2, X3and X4 have the values listed in the table Q.
Table 230 O:
Table 230 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G.114, X1, X2, X3and X4 have the values listed in the table Q.
Table 231 O:
Table 231 Q provides 54 compounds of formula (II-B) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 15, X1, X2, X3and X4 have the values listed in the table Q.
Table 232 O:
Figure imgf000190_0001
Table 2330:
Table 233 provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.001, X1, X2, X3and X4 have the values listed in the table Q.
Table 234 O:
Table 234Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.002, X1, X2, X3and X4 have the values listed in the table Q.
Table 235 O:
Table 235Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.003, X1, X2, X3and X4 have the values listed in the table Q.
Table 236 O:
Table 236Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.004, X1, X2, X3and X4 have the values listed in the table Q.
Table 237 0:
Table 237Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.005, X1, X2, X3and X4 have the values listed in the table Q.
Table 238 0:
Table 238Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.006, X1, X2, X3and X4 have the values listed in the table Q.
Table 239 O:
Table 239Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.007, X1, X2, X3and X4 have the values listed in the table Q.
Table 240 O:
Table 240Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.008, X1, X2, X3and X4 have the values listed in the table Q.
Table 241 0:
Table 241Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.009, X1, X2, X3and X4 have the values listed in the table Q.
Table 242 0:
Table 242Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.010, X1, X2, X3and X4 have the values listed in the table Q.
Table 243 0:
Table 243 Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.Ol 1, X1, X2, X3and X4 have the values listed in the table Q.
Table 244 0:
Table 244Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.012, X1, X2, X3and X4 have the values listed in the table Q.
Table 245 0:
Table 245Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.013, X1, X2, X3and X4 have the values listed in the table Q.
Table 246 O:
Table 246Q provides 54 compounds of formula (I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.014, X1, X2, X3and X4 have the values listed in the table Q. Table 247 0:
Table 247Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.015, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 248 O:
Table 248Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.016, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 249 O:
Table 249Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.017, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 250 O:
Table 250Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.018, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 251 O:
Table 251 Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.019, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 252 0:
Table 252Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.020, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 253 0:
Table 253Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.021, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 2540:
Table 254Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.022, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 255 0:
Table 255Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.023, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 256 0:
Table 256Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.024, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 257 0:
Table 257Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.025, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 258 0:
Table 258Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.026, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 259 0:
Table 259Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.027, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 260 0:
Table 260Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.028, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 261 O:
Table 261Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.029, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 262 O:
Table 262Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.030, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 263 O:
Table 263 Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.031, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 264 O:
Table 264Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.032, X1, X2, X3and X4 have the values listed in the tab e Q. Table 265 0:
Table 265Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.033, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 266 O:
Table 266Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.034, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 267 O:
Table 267Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.035, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 268 O:
Table 268Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.036, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 269 O:
Table 269Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.037, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 270 0:
Table 270Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.038, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 271 0:
Table 271 Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.039, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 272 0:
Table 272Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.040, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 273 0:
Table 273 Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.041, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 274 0:
Table 274Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.042, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 275 0:
Table 275Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.043, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 276 0:
Table 276Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.044, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 277 0:
Table 277Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.045, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 278 0:
Table 278Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.046, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 279 O:
Table 279Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.047, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 280 O:
Table 280Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.048, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 281 O:
Table 281 Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.049, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 282 O:
Table 282Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.050, X1, X2, X3and X4 have the values listed in the tab e Q. Table 283 0:
Table 283Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.051, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 284 O:
Table 284Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.052, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 285 O:
Table 285Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.053, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 286 O:
Table 286Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.054, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 287 O:
Table 287Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.055, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 288 0:
Table 288Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.056, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 289 0:
Table 289Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.057, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 290 0:
Table 290Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.058, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 291 0:
Table 291Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.059, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 292 0:
Table 292Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.060, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 293 0:
Table 293 Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.061, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 294 0:
Table 294Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.062, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 295 0:
Table 295Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.063, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 296 0:
Table 296Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.064, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 297 O:
Table 297Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.065, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 298 O:
Table 298Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.066, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 299 O:
Table 299Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.067, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 300 O:
Table 300Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.068, X1, X2, X3and X4 have the values listed in the tab e Q. Table 301Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.069, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 302 O:
Table 302Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.070, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 303 O:
Table 303Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.071, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 304 O:
Table 304Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.072, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 305 0:
Table 305Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.073, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 306 0:
Table 306Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.074, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 307 0:
Table 307Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.075, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 308 O:
Table 308Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.076, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 309 O:
Table 309Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.077, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 3 0_Qi
Table 3 OQ provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.078,
X1, X2, X3and X4 have the values listed in the tab e Q.
Table 311 O:
Table 311 Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.079, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 3 2_Ql
Table 3 2Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.080, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 3 3_Qi
Table 3 3Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.081,
X1, X2, X3and X4 have the values listed in the tab e Q.
Table 3 4_Qi
Table 3 4Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.082,
X1, X2, X3and X4 have the values listed in the tab e Q.
Table 3 5_Qi
Table 3 5Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.083,
X1, X2, X3and X4 have the values listed in the tab e Q.
Table 3 6_Ql
Table 3 6Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.084,
X1, X2, X3and X4 have the values listed in the tab e Q.
Table 3
Table 3 7Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.085, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 3 8_Ql
Table 318Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.086, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 319 0:
Table 3 9Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.087, X1, X2, X3and X4 have the values listed in the tab e Q. Table 320 0:
Table 320Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.088, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 321 O:
Table 312Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.089, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 322 O:
Table 322Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.090, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 323 O:
Table 323Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.091, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 324 O:
Table 324Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.092, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 325 0:
Table 325Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.093, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 326 0:
Table 326Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.094, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 327 0:
Table 327Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.095, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 328 0:
Table 328Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.096, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 329 0:
Table 329Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.097, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 330 0:
Table 330Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.098, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 331 0:
Table 331Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.099, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 332 0:
Table 332Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.100, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 333 0:
Table 333Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.101, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 334 O:
Table 334Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.102, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 335 O:
Table 335Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.103, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 336 O:
Table 336Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.104, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 337 O:
Table 337Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.105, X1, X2, X3and X4 have the values listed in the tab e Q. Table 338 0:
Table 338Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.106, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 339 O:
Table 339Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.107, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 340 O:
Table 340Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 08, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 341 O:
Table 341Q provides 54 compounds of formula ( -C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.109, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 342 O:
Table 342Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.110, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 343 0:
Table 343Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.111 , X1, X2, X3and X4 have the values listed in the tab e Q.
Table 344 0:
Table 344Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.112, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 345 0:
Table 345Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.113, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 346 0:
Table 346Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.114, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 347 0:
Table 347Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.115, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 348 0:
Table 348Q provides 54 compounds of formula ( C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.116, X1, X2, X3and X4 have the values listed in the tab e Q.
Figure imgf000196_0001
Table 349 0:
Table 349Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.001, X1, X2, X3and X4 have the values listed in the table Q.
Table 350 0:
Table 350Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.002, X1, X2, X3and X4 have the values listed in the table Q.
Table 351 O:
Table 351Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.003, X1, X2, X3and X4 have the values listed in the table Q.
Table 352 O:
Table 352Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.004, X1, X2, X3and X4 have the values listed in the table Q. Table 353 0:
Table 353Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.005, X1, X2, X3and X4 have the values listed in the table Q.
Table 354 O:
Table 354Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.006, X1, X2, X3and X4 have the values listed in the table Q.
Table 355 O:
Table 355Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.007, X1, X2, X3and X4 have the values listed in the table Q.
Table 356 O:
Table 356Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.008, X1, X2, X3and X4 have the values listed in the table Q.
Table 357 O:
Table 357Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.009, X1, X2, X3and X4 have the values listed in the table Q.
Table 358 0:
Table 358Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.010, X1, X2, X3and X4 have the values listed in the table Q.
Table 359 0:
Table 359Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.Ol 1, X1, X2, X3and X4 have the values listed in the table Q.
Table 360 0:
Table 360Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.012, X1, X2, X3and X4 have the values listed in the table Q.
Table 361 0:
Table 361Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.013, X1, X2, X3and X4 have the values listed in the table Q.
Table 362 0:
Table 362Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.014, X1, X2, X3and X4 have the values listed in the table Q.
Table 363 0:
Table 363Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.015, X1, X2, X3and X4 have the values listed in the table Q.
Table 364 0:
Table 364Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.Ol 6, X1, X2, X3and X4 have the values listed in the table Q.
Table 365 0:
Table 365Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.017, X1, X2, X3and X4 have the values listed in the table Q.
Table 366 0:
Table 366Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.Ol 8, X1, X2, X3and X4 have the values listed in the table Q.
Table 367 O:
Table 367Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.019, X1, X2, X3and X4 have the values listed in the table Q.
Table 368 O:
Table 368Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.020, X1, X2, X3and X4 have the values listed in the table Q.
Table 369 O:
Table 369Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.021, X1, X2, X3and X4 have the values listed in the table Q.
Table 370 O:
Table 370Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.022, X1, X2, X3and X4 have the values listed in the table Q. Λ nr
- 196 -
Table 371 0:
Table 371Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.023, X1, X2, X3and X4 have the values listed in the table Q.
Table 372 O:
Table 372Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.024, X1, X2, X3and X4 have the values listed in the table Q.
Table 373 O:
Table 373Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.025, X1, X2, X3and X4 have the values listed in the table Q.
Table 374 O:
Table 374Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.026, X1, X2, X3and X4 have the values listed in the table Q.
Table 375 O:
Table 375Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.027, X1, X2, X3and X4 have the values listed in the table Q.
Table 376 0:
Table 376Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.028, X1, X2, X3and X4 have the values listed in the table Q.
Table 377 0:
Table 377Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.029, X1, X2, X3and X4 have the values listed in the table Q.
Table 378 0:
Table 378Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.030, X1, X2, X3and X4 have the values listed in the table Q.
Table 379 0:
Table 379Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.031, X1, X2, X3and X4 have the values listed in the table Q.
Table 380 0:
Table 380Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.032, X1, X2, X3and X4 have the values listed in the table Q.
Table 381 0:
Table 381Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.033, X1, X2, X3and X4 have the values listed in the table Q.
Table 382 0:
Table 382Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.034, X1, X2, X3and X4 have the values listed in the table Q.
Table 383 0:
Table 383Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.035, X1, X2, X3and X4 have the values listed in the table Q.
Table 384 0:
Table 384Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.036, X1, X2, X3and X4 have the values listed in the table Q.
Table 385 O:
Table 385Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.037, X1, X2, X3and X4 have the values listed in the table Q.
Table 386 O:
Table 386Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.038, X1, X2, X3and X4 have the values listed in the table Q.
Table 387 O:
Table 387Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.039, X1, X2, X3and X4 have the values listed in the table Q.
Table 388 O:
Table 388Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.040, X1, X2, X3and X4 have the values listed in the table Q.
Table 389 O: Table 389Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.041, X1, X2, X3and X4 have the values listed in the table Q.
Table 390 O:
Table 390Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.042, X1, X2, X3and X4 have the values listed in the table Q.
Table 391 O:
Table 391Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.043, X1, X2, X3and X4 have the values listed in the table Q.
Table 392 0:
Table 392Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.044, X1, X2, X3and X4 have the values listed in the table Q.
Table 393 0:
Table 393Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.045, X1, X2, X3and X4 have the values listed in the table Q.
Table 394 0:
Table 394Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.046, X1, X2, X3and X4 have the values listed in the table Q.
Table 395 0:
Table395Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.047, X1, X2, X3and X4 have the values listed in the table Q.
Table 396 O:
Table 396Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.048, X1, X2, X3and X4 have the values listed in the table Q.
Table 397 O:
Table 397Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.049, X1, X2, X3and X4 have the values listed in the table Q.
Table 398 O:
Table 398Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.050, X1, X2, X3and X4 have the values listed in the table Q.
Table 399 O:
Table 399Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.051, X1, X2, X3and X4 have the values listed in the table Q.
Table 400 0:
Table 400Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.052, X1, X2, X3and X4 have the values listed in the table Q.
Table 401 O:
Table 401Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.053, X1, X2, X3and X4 have the values listed in the table Q.
Table 402 O:
Table 402Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.054, X1, X2, X3and X4 have the values listed in the table Q.
Table 403 O:
Table 403Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.055, X1, X2, X3and X4 have the values listed in the table Q.
Table 404 O:
Table 404Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.056, X1, X2, X3and X4 have the values listed in the table Q.
Table 405 0:
Table 405Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.057, X1, X2, X3and X4 have the values listed in the table Q.
Table 406 0:
Table 406Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.058, X1, X2, X3and X4 have the values listed in the table Q.
Table 407 0:
Table 407Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.059, X1, X2, X3and X4 have the values listed in the table Q. no
Table 408 0:
Table 408Q provides 54 compounds of formula (ITC) wherein G1 is oxygen, R1 is hydrogen, R2 is G.060, X1, X2, X3and X4 have the values listed in the table Q.
Table 409 O:
Table 409Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.061, X1, X2, X3and X4 have the values listed in the table Q.
Table 410 O:
Table 410Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.062, X1, X2, X3and X4 have the values listed in the table Q.
Table 411 O:
Table 411Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.063, X1, X2, X3and X4 have the values listed in the table Q.
Table 412 O:
Table 412Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.064, X1, X2, X3and X4 have the values listed in the table Q.
Table 413 O:
Table 413Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.065, X1, X2, X3and X4 have the values listed in the table Q.
Table 414 0:
Table 414Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.066, X1, X2, X3and X4 have the values listed in the table Q.
Table 415 0:
Table 415Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.067, X1, X2, X3and X4 have the values listed in the table Q.
Table 416 0:
Table 416Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.068, X1, X2, X3and X4 have the values listed in the table Q.
Table 417 0:
Table 417Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.069, X1, X2, X3and X4 have the values listed in the table Q.
Table 418 0:
Table 418Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.070, X1, X2, X3and X4 have the values listed in the table Q.
Table 419 0:
Table 419Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.071, X1, X2, X3and X4 have the values listed in the table Q.
Table 420 0:
Table 420Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.072, X1, X2, X3and X4 have the values listed in the table Q.
Table 421 0:
Table 421Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.073, X1, X2, X3and X4 have the values listed in the table Q.
Table 422 O:
Table 422Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.074, X1, X2, X3and X4 have the values listed in the table Q.
Table 423 O:
Table 423Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.075, X1, X2, X3and X4 have the values listed in the table Q.
Table 424 O:
Table 424Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.076, X1, X2, X3and X4 have the values listed in the table Q.
Table 425 O:
Table 425Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.077, X1, X2, X3and X4 have the values listed in the table Q. Table 426 0:
Table 426Q provides 54 compounds of formula ( I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.078, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 427 O:
Table 427Q provides 54 compounds of formula ( I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.079, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 428 O:
Table 428Q provides 54 compounds of formula ( I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.080, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 429 O:
Table 429Q provides 54 compounds of formula ( I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.081, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 430 O:
Table 43 OQ provides 54 compounds of formula ( I-C) wherein G is oxyi ;en, R1 is hydrogen, R2 is G.082, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 431 0:
Table 431Q provides 54 compounds of formula ( II--CC)) wherein G1 is oxyi ;en, R1 is hydrogen, R2 is G.083, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 432 0:
Table 432Q provides 54 compounds of formula ( II--CC)) wherein G1 is oxyi 'en, R1 is hydrogen, R2 is G.084, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 433 0:
Table 433Q provides 54 compounds of formula ( II--CC)) wherein G1 is oxyi ;en, R1 is hydrogen, R2 is G.085, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 434 0:
Table 434Q provides 54 compounds of formula ( II--CC)) wherein G1 is oxyi 'en, R1 is hydrogen, R2 is G.086, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 435 0:
Table 435Q provides 54 compounds of formula ( II--CC)) wherein G1 is oxyi *en, R1 is hydrogen, R2 is G.087, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 436 0:
Table 436Q provides 54 compounds of formula ( II--CC)) wherein G1 is oxy; en, R1 is hydrogen, R2 is G. X1, X2, X3and X4 have the values listed in the tab e Q.
Table 437 0:
Table 437Q provides 54 compounds of formula ( II--CC)) wherein G1 is oxyi ;en, R1 is hydrogen, R2 is G.089, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 438 0:
Table 438Q provides 54 compounds of formula ( II--CC)) wherein G1 is oxyi ;en, R1 is hydrogen, R2 is G.090, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 439 0:
Table 439Q provides 54 compounds of formula ( II--CC)) wherein G1 is oxyi 'en, R1 is hydrogen, R2 is G.091, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 440 O:
Table 440Q provides 54 compounds of formula ( II--CC)) wherein G1 is oxyi *en, R1 is hydrogen, R2 is G.092, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 441 O:
Table 441Q provides 54 compounds of formula ( II--CC)) wherein G1 is oxyi 'en, R1 is hydrogen, R2 is G.093, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 442 O:
Table 442Q provides 54 compounds of formula ( II--CC)) wherein G1 is oxyi *en, R1 is hydrogen, R2 is G.094, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 443 O:
Table 443Q provides 54 compounds of formula ( I-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.095, X1, X2, X3and X4 have the values listed in the tab e Q.
Table 444 O: ^QQ
Table 444Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.096, X1, X2, X3and X4 have the values listed in the table Q.
Table 445 O:
Table 445Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.097, X1, X2, X3and X4 have the values listed in the table Q.
Table 446 O:
Table 446Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.098, X1, X2, X3and X4 have the values listed in the table Q.
Table 447 0:
Table 447Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.099, X1, X2, X3and X4 have the values listed in the table Q.
Table 448 0:
Table 448Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 00, X1, X2, X3and X4 have the values listed in the table Q.
Table 449 0:
Table 449Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 01, X1, X2, X3and X4 have the values listed in the table Q.
Table 450 0:
Table 450Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 02, X1, X2, X3and X4 have the values listed in the table Q.
Table 451 O:
Table 451Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 03, X1, X2, X3and X4 have the values listed in the table Q.
Table 452 O:
Table 452Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.104, X1, X2, X3and X4 have the values listed in the table Q.
Table 453 O:
Table 453Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 05, X1, X2, X3and X4 have the values listed in the table Q.
Table 454 O:
Table 4543Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.106, X1, X2, X3and X4 have the values listed in the table Q.
Table 455 0:
Table 455Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 07, X1, X2, X3and X4 have the values listed in the table Q.
Table 456 O:
Table 456Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 08, X1, X2, X3and X4 have the values listed in the table Q.
Table 457 O:
Table 457Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 09, X1, X2, X3and X4 have the values listed in the table Q.
Table 458 O:
Table 458Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 10, X1, X2, X3and X4 have the values listed in the table Q.
Table 459 O:
Table 459Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.111 , X1, X2, X3and X4 have the values listed in the table Q.
Table 460 O:
Table 460Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.112, X1, X2, X3and X4 have the values listed in the table Q.
Table 461 0:
Table 461Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 13, X1, X2, X3and X4 have the values listed in the table Q.
Table 462 0:
Table 462Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.114, X1, X2, X3and X4 have the values listed in the table Q. Table 463 0:
Table 463Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G. l 15, X1, X2, X3and X4 have the values listed in the table Q.
Table 464 O:
Table 464Q provides 54 compounds of formula (II-C) wherein G1 is oxygen, R1 is hydrogen, R2 is G.116, X1, X2, X3and X4 have the values listed in the table .
Figure imgf000203_0003
Figure imgf000203_0001
Table 233P
Table 233P provides 3240 compounds of formula (I-D) wherein Het is Het.Ol, X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 234P
Table 234P provides 3240 compounds of formula (I-D) wherein Het is Het.02, X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 235 P
Table 235P provides 3240 compounds of formula (I-D) wherein Het is Het.03, X1, X2, X3, Y1, Y2, Y3, X and R5 have the values listed in the table P.
Table 236 P
Table 236P provides X2, X3, Y1, Y2, Y3, X and R5 have the valu
Figure imgf000203_0002
Table 237 P
Table 237P provides 3240 compounds of formula (II-D) wherein Het is Het.Ol, X1, X2, X3, Y1, Y2, Y3, X' and R5 have the values listed in the table P.
Table 238 P 2Q2
Table 238P provides 3240 compounds of formula (II-D) wherein Het is Het.02, X1, X2, X3, Y1, Y2, Y3, X' and R5 have the values listed in the table P.
Table 239 P
Table 239P provides 3240 compounds of formula (II-D) wherein Het is Het.03, X1, X2, X3, Y1, Y2, Y3, X' and R5 have the values listed in the table P.
Table 240 P
Table 240P provides X2, X3, Y1, Y2, Y3, X' and R5 have the valu
Figure imgf000204_0001
Table 4650
Table 465Q provides 54 compounds of formula (I-E) wherein G1 is oxygen, R1 is hydrogen, Het is Het.Ol, X1, X2, X3and X4 have the values listed in the table Q.
gen, Het is gen, Het is gen, Het is
Figure imgf000204_0002
Table 4690
Table 469Q provides 54 compounds of formula (II-E) wherein G1 is oxygen, R1 is hydrogen, Het is Het.Ol, X1, X2, X3and X4 have the values listed in the table Q.
Table 470O
Table 470Q provides 54 compounds of formula (II-E) wherein G1 is oxygen, R1 is hydrogen, Het is Het.02, X1, X2, X3and X4 have the values listed in the table Q.
Table 4710
Table 471Q provides 54 compounds of formula (II-E) wherein G1 is oxygen, R1 is hydrogen, Het is Het.03, X1, X2, X3and X4 have the values listed in the table Q.
Table 4720
Table 472Q provides 54 compounds of formula (II-E) wherein G1 is oxygen, R1 is hydrogen, Het is Het.04, X1, X2, X3and X4 have the values listed in the table Q. „Λ„
Figure imgf000205_0001
Table 4730
Table 473 Q provides 54 compounds of formula (I-F) wherein G1 is oxygen, R1 is hydrogen, Het is Het.Ol, X1, X2, X3and X4 have the values listed in the table Q.
Table 4740
Table 474Q provides 54 compounds of formula (I-F) wherein G1 is oxygen, R1 is hydrogen, Het is Het.02, X1, X2, X3and X4 have the values listed in the table Q.
Table 4750
TTaabbllee 447755QQ provides 54 compounds of formula (I-F) wherein G1 is oxygen, R1 is hydrogen, Het is HHeett..0033,, XX11,, i X2, X3and X4 have the values listed in the table Q.
gen, Het is
Figure imgf000205_0002
Table 4770
Table 477Q provides 54 compounds of formula (II-F) wherein G1 is oxygen, R1 is hydrogen, Het is Het.Ol, X1, X2, X3and X4 have the values listed in the table Q.
Table 4780
Table 478Q provides 54 compounds of formula (II-F) wherein G1 is oxygen, R1 is hydrogen, Het is Het.02, X1, X2, X3and X4 have the values listed in the table Q.
Table 4790
Table 479Q provides 54 compounds of formula (II-F) wherein G1 is oxygen, R1 is hydrogen, Het is Het.03, X1, X2, X3and X4 have the values listed in the table Q.
Table 480O
Table 480Q provides 54 compounds of formula (II-F) wherein G1 is oxygen, R1 is hydrogen, Het is Het.04, X1, X2, X3and X4 have the values listed in the table Q.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing insects of the family Curculionidae, preferably in for use in controlling and/or preventing Anthonomus grandis.
Additional examples of insects from the family of Curculionidae. are Anthonomus corvulus, Anthonomus elutus, Anthonomus elongatus, Anthonomus eugenii, Anthonomus consors, Anthonomus haematopus, Anthonomus lecontei, Anthonomus molochinus, Anthonomus morticinus, Anthonomus musculus, Anthonomus nigrinus, Anthonomus phyllocola, Anthonomus pictus, Anthonomus pomorum, 2Q4
Anthonomus quadrigibbus, Anthonomus rectirostris, Anthonomus rubi, Anthonomus santacruzi, Anthonomus signatus, Anthonomus subfasciatus, and Anthonomus tenebrosus.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use against Anthonomus grandis in cotton.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing soil pests.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing corn rootworm, in particular for use against corn root worm from the genus Diabrotica.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing Diabrotica virgifera.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to
116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing Diabrotica barberi.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing Diabrotica undecimpunctata howardi.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing wireworms, in particular Agriotes spp.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing Agriotes spp. in cereals, potato or corn.
Additional examples of Agriotes spp. include Agriotes lineatus, Agriotes obscurus, Agriotes brevis, Agriotes gurgistanus, Agriotes sputator, Agriotes ustulatus, Ctenicera destructor, and Limonius californicus.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to
116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing grubs, in particular white grubs.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1 Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing Phyllophaga spp., particularly on corn, soybean or cotton.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing Diloboderus spp. particularly on corn, soybean or cotton. 2Q5
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing Popillia japonica, particularly on corn, soybean or cotton.
Additional examples of white grubs include Phyllophaga anxia, Phyllophaga crinite, Phyllophaga subnitida, Diloboderus abderus.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing termites, e.g. on sugarcane.
Examples of termites include Reticulitermes, Coptotermes, Macrotermes, Microtermes, Globitermes. Specific of subterranean termites include Reticulitermes flavipes, Reticulitermes hesperus, Reticulitermes verginicus, Reticulitermes hageni, Reticulitermes speratus, Reticulitermes lucifugus, Heterotermes aureus, Coptotermes formosanus, Coptotermes acinaciformis, Coptotermes curvignathus, Nasutitermes exitiosus, Nasutitermes walkeri, Mastotermes darwiniensis, Schedorhinotermes spp, Macrotermes bellicosus, Macrotermes spp., Globitermes sulphureus, Odontotermes spp.. Specific examples of dry wood termites include Incisitermes minor, Marginitermes hubbardi, Cryptotermes brevis, Kalotermes flavicollis. Additional examples of termites include procornitermes spp. and procornitermes araujoi
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris spp..
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing Scaptocoris castaneus, in particular on cereals, soybean or corn.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing cutworms, e.g. agrotis spp..
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing Agrotis ipsilon, particularly on cereals, canola, soybean or corn.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to
116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing millipedes, e.g. Julus spp..
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing Julus spp., particularly on cereals, canola, soybean & corn.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing broca gigante, e.g. Telchin licus, particularly on sugarcane. . _ ,
- 206 -
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing whitefly.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing Bemisia tabaci, particularly on vegetables, cotton, soybean, or potatoes.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing Trialeurodes vapor ariorum, particularly on vegetables, cotton, soybean, or potatoes.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to
116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing stinkbugs, in particular Euschistus spp.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use in controlling and/or preventing Euschistus spp. , particularly in soybean.
Examples of stinkbugs include Nezara spp. (e.g. Nezara viridula, Nezara antennata, Nezara hilare), Piezodorus spp. (e.g. Piezodorus guildinii), Acrosternum spp. Euchistus spp. (e.g. Euchistus heros, Euschistus servus), Halyomorpha halys, Plautia crossota, Riptortus clavatus, Rhopalus msculatus, Antestiopsis orbitalus, Dichelops spp. (e.g. Dichelops furcatus, Dichelops melacanthus), Eurygaster spp. (e.g. Eurygaster intergriceps, Eurygaster maura), Oebalus spp. (e.g. Oebalus mexicana, Oebalus poecilus, Oebalus pugnase, Scotinophara spp. (e.g. Scotinophara lurida, Scotinophara coarctata).
Preferred targets include Antestiopsis orbitalus, Dichelops furcatus, Dichelops melacanthus, Euchistus heros, Euschistus servus, Nezara viridula, Nezara hilare, Piezodorus guildinii, Halyomorpha halys. In one embodiment the stinkbug target is Nezara viridula, Piezodorus spp., Acrosternum spp, Euchistus heros.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use against rice pests.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use against stemborer, particularly in rice.
Examples of stemborers include Chilo sp, Chilo suppressalis, Chilo polychrysus, Chilo auricilius, Scirpophaga spp., Scirpophaga incertulas, Scirpophaga innotata, Scirpophaga nivella
Sesamia sp, Sesamia inferens.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use against leaffolder, particularly in rice.
Examples of leaffolders include Cnaphalocrocis spp., Cnaphalocrocis medinalis, Marasmia spp., Marasmia patnalis, Marasmia exigua. 2Q7
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use against hoppers, particularly in rice.
Examples of Hoppers include Nephotettix spp., Nephotettix virescens, Nephotettix nigropictus, Nephotettix malayanus, Nephotettix cincticeps, Nilaparvata lugens, Sogatella furcifera.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use against gallmidge, particularly in rice.
Examples of Gall midge include Orseolia sp, Orseolia oryzae.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to
116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use against whorl maggot, particularly in rice.
Examples of whorl maggots include Hydrellia sp, Hydrellia philippina.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use against Rice bugs, particularly in rice.
Examples of rice bugs include Leptocorisa sp, Leptocorisa oratorius, Leptocorisa chinensis, Leptocorisa acuta.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use against Black bugs, particularly in rice.
Examples of Black bugs include Scotinophara sp, Scotinophara coarctata, Scotinophara lurida, Scotinophara latiuscula.
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use against plutella spp..
In one embodiment the invention provides a compound selected from Tables IP to 116P, 1Q to 116Q, 233Q to 348Q, 233P to 236P, 465Q to 468Q, 473Q to 476Q for use against Plutella xylostella, particularly in brassica crops.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing insects of the family Curculionidae, preferably in for use in controlling and/or preventing Anthonomus grandis.
Additional examples of insects from the family of Curculionidae. are Anthonomus corvulus, Anthonomus elutus, Anthonomus elongatus, Anthonomus eugenii, Anthonomus consors, Anthonomus haematopus, Anthonomus lecontei, Anthonomus molochinus, Anthonomus morticinus, Anthonomus musculus, Anthonomus nigrinus, Anthonomus phyllocola, Anthonomus pictus, Anthonomus pomorum, Anthonomus quadrigibbus, Anthonomus rectirostris, Anthonomus rubi, Anthonomus santacruzi,
Anthonomus signatus, Anthonomus subfasciatus, and Anthonomus tenebrosus. ΛΟ
- 2Uo -
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Q for use against Anthonomus grandis in cotton.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing soil pests.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing corn rootworm, in particular for use against corn root worm from the genus Diabrotica.
In one embodiment the invention provides a compound selected from Tables 117P to 232P,
117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing corn Diabrotica virgifera.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing corn Diabrotica barberi.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing corn Diabrotica undecimpunctata howardi.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing wireworms, in particular Agriotes spp.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing Agriotes spp. in cereals, potato or corn.
Additional examples of Agriotes spp. include Agriotes Uneatus, Agriotes obscurus, Agriotes brevis, Agriotes gurgistanus, Agriotes sputator, Agriotes ustulatus, Ctenicera destructor, and Limonius californicus.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing grubs, in particular white grubs.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing Phyllophaga spp. , particularly on corn, soybean or cotton.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing Diloboderus spp. particularly on corn, soybean or cotton. 2Q9
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing Popillia japonica, particularly on corn, soybean or cotton.
Additional examples of white grubs include Phyllophaga anxia, Phyllophaga crinite, Phyllophaga subnitida, Diloboderus abderus.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing termites, e.g. on sugarcane.
Examples of termites include Reticulitermes, Coptotermes, Macrotermes, Microtermes, Globitermes. Specific of subterranean termites include Reticulitermes flavipes, Reticulitermes hesperus, Reticulitermes verginicus, Reticulitermes hageni, Reticulitermes speratus, Reticulitermes lucifugus, Heterotermes aureus, Coptotermes formosanus, Coptotermes acinaciformis, Coptotermes curvignathus, Nasutitermes exitiosus, Nasutitermes walkeri, Mastotermes darwiniensis, Schedorhinotermes spp, Macrotermes bellicosus, Macrotermes spp., Globitermes sulphureus, Odontotermes spp.. Specific examples of dry wood termites include Incisitermes minor, Marginitermes hubbardi, Cryptotermes brevis, Kalotermes flavicollis. Additional examples of termites include procornitermes spp. and procornitermes araujoi
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris spp..
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing Scaptocoris castaneus, in particular on cereals, soybean or corn.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing cutworms, e.g. agrotis spp..
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing Agrotis ipsilon, particularly on cereals, canola, soybean or corn.
In one embodiment the invention provides a compound selected from Tables 117P to 232P,
117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing millipedes, e.g. Julus spp..
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing Julus spp., particularly on cereals, canola, soybean & corn.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing broca gigante, e.g. Telchin licus, particularly on sugarcane. In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing whitefly.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing Bemisia tabaci, particularly on vegetables, cotton, soybean, or potatoes.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing Trialeurodes vapor ariorum, particularly on vegetables, cotton, soybean, or potatoes.
In one embodiment the invention provides a compound selected from Tables 117P to 232P,
117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing stinkbugs, in particular Euschistus spp.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use in controlling and/or preventing Euschistus spp. , particularly in soybean.
Examples of stinkbugs include Nezara spp. (e.g. Nezara viridula, Nezara antennata, Nezara hilare), Piezodorus spp. (e.g. Piezodorus guildinii), Acrosternum spp. Euchistus spp. (e.g. Euchistus heros, Euschistus servus), Halyomorpha halys, Plautia crossota, Riptortus clavatus, Rhopalus msculatus, Antestiopsis orbitalus, Dichelops spp. (e.g. Dichelops furcatus, Dichelops melacanthus), Eurygaster spp. (e.g. Eurygaster intergriceps, Eurygaster maura), Oebalus spp. (e.g. Oebalus mexicana, Oebalus poecilus, Oebalus pugnase, Scotinophara spp. (e.g. Scotinophara lurida, Scotinophara coarctata).
Preferred targets include Antestiopsis orbitalus, Dichelops furcatus, Dichelops melacanthus, Euchistus heros, Euschistus servus, Nezara viridula, Nezara hilare, Piezodorus guildinii, Halyomorpha halys. In one embodiment the stinkbug target is Nezara viridula, Piezodorus spp., Acrosternum spp, Euchistus heros.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use against rice pests.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use against stemborer, particularly in rice.
Examples of stemborers include Chilo sp, Chilo suppressalis, Chilo polychrysus, Chilo auricilius, Scirpophaga spp., Scirpophaga incertulas, Scirpophaga innotata, Scirpophaga nivella
Sesamia sp, Sesamia inferens.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use against leaffolder, particularly in rice.
Examples of leaffolders include Cnaphalocrocis spp., Cnaphalocrocis medinalis, Marasmia spp., Marasmia patnalis, Marasmia exigua. In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use against hoppers, particularly in rice.
Examples of Hoppers include Nephotettix spp., Nephotettix virescens, Nephotettix nigropictus, Nephotettix malayanus, Nephotettix cincticeps, Nilaparvata lugens, Sogatella furcifera.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use against gallmidge, particularly in rice.
Examples of Gall midge include Orseolia sp, Orseolia oryzae.
In one embodiment the invention provides a compound selected from Tables 117P to 232P,
117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use against whorl maggot, particularly in rice.
Examples of whorl maggots include Hydrellia sp, Hydrellia philippina.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use against Rice bugs, particularly in rice.
Examples of rice bugs include Leptocorisa sp, Leptocorisa oratorius, Leptocorisa chinensis, Leptocorisa acuta.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use against Black bugs, particularly in rice.
Examples of Black bugs include Scotinophara sp, Scotinophara coarctata, Scotinophara lurida, Scotinophara latiuscula.
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use against plutella spp..
In one embodiment the invention provides a compound selected from Tables 117P to 232P, 117Q to 232Q, 349Q to 464Q, 237P to 240P, 469Q to 472Q, 477Q to 480Qfor use against Plutella xylostella, particularly in brassica crops.
The compounds of the invention may be made by a variety of methods as shown in the following Schemes.
Figure imgf000214_0001
Scheme 2
Figure imgf000215_0001
deprotection deprotection
Figure imgf000215_0002
(XVI) (IX) (V)
1) Compounds of formula (V), wherein R13 is Ci-C6alkyl,can be prepared by deprotection of a compound of formula (XVII), wherein R13 is Ci-C6alkyl and wherein P is a protecting group for an alcohol. Various protecting groups can be used, such as those described in T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis. Depending on the protecting group used, different methods are available to achieve the deprotection, as is also described in the previous reference. For instance, if such a protecting group is a trimethylsilyl group, these reactions are usually carried out in the presence of a suitable fluoride ion source, such as tetrabutylammonium fluoride optionally in a solvent, such as ethanol or tetrahydrofuran, or mixtures thereof. The reaction is carried out at a temperature of from 0°C to 100°C, preferably from 0°C to ambient temperature. The alcohol deprotection reactions are known in the literature and can be achieved using methods known to a person skilled in the art.
2) Compounds of formula (XVII) , wherein R13 is Ci-C6alkyl, can be prepared by reacting a compound of formula (VI) wherein P is a protecting group, for example a trimethylsilyl group, with a compound of formula (IX), wherein R13 is Ci-C6alkyl, in the presence of a catalyst, such as
tetrakis(triphenylphosphine)palladium or PdCl2(PPh3)2. These reactions are usually carried out in the presence of a suitable solvent, such as toluene, dichloromethane or chlorobenzene. The reaction is carried out at a temperature of from -78°C to 100°C, preferably from 0°C to ambient temperature. Alternatively, the hydrostannylation reaction can be achieved under radical conditions or in the presence of copper salts. Stannylation of enynes are known in the literature (see references in Pancrazi and al. J. Org. Chem. 1997, 62, 7768-7780) and can be achieved using methods known to a person skilled in the art.
3) Compounds of formula (VI) can be prepared by reacting a compound of formula (VIII) wherein P is a protecting group, for example a trimethylsilyl group, with a compound of formula (VII), in a stepwise process. First a compound of formula (VIII) wherein P is a protecting group, for example a trimethylsilyl group, is treated with a metallating agent, such as butyl lithium or a Grignard reagent, such as ethyl magnesium bromide to form an intermediate that is then reacted with a compound of formula (VII). These reactions are usually carried out in the presence of a suitable solvent, such as toluene, dichloromethane or tetrahydrofuran. The reaction is carried out at a temperature of from -40°C to 100°C, preferably from 0°C to ambient temperature. The alkylation of ketones are known in the literature and can be achieved using methods known to a person skilled in the art.
4) Compounds of formula (V), wherein R13 is Ci-Cealkyl, can be prepared from compounds of formula (XVI) using the method described in 2).
5) Compounds of formula (XVI) can be prepared from compounds of formula (VI) using the method described in 1).
Scheme 3
Figure imgf000216_0001
6) Compounds of formula (IV), wherein R13 is Ci-C6alkyl, can be prepared by dehydration of a compound of formula (V) wherein R13 is Ci-Cealkyl. Such reactions are usually carried out in the presence of an acid, for example an inorganic acid, such as hydrochloric acid or sulfuric acid, or a sulfonic acid, such as methanesulfonic acid, optionally in a solvent, such as water, ethanol or
tetrahydrofuran, or mixtures thereof. The reaction is carried out at a temperature of from 0°C to 100°C, preferably from 40°C to 80°C. Alternatively, dehydration can be carried out using a dehydrating agent, such as phosphorus pentoxide, in a solvent, such as chloroform, at a temperature of from -20°C to 50°, preferably at 0°C. Alternatively, cyclisation can be carried out under Mitsunobu conditions involving treatment of a compound of formula (V) with a phosphine, such as triphenylphosphine, and an azodicarboxylate reagent, such as diethyl azodicarboxylate, diisopropyl azodicarboxylate or dicyclohexyl azodicarboxylate, in a solvent, such as tetrahydrofuran, at a temperature of from 0°C to 80°C, preferably from 0°C to ambient temperature.
Figure imgf000216_0002
7) Compounds of formula (II-B) wherein Rx is Ci-Ci5alkoxy can be prepared by reacting a compound of formula (XII) wherein X1 is a leaving group, for example a halogen, such as bromo, and wherein Rx is Ci-Ci5alkoxy with a compound of formula (IV), wherein R13 is Ci-Cealkyl, in the presence of a catalyst, such as tetrakis(triphenylphosphine)palladium or PdCl2(PPh3)2, a ligand, such as a triphenylphosphine, and an additive, such as lithium chloride, or copper iodide. The reaction is carried out in a suitable solvent, such as toluene, at a temperature of from 50°C to 200°C, preferably from 100°C to 150°C, in particular at 1 15°C. The Stille couplings are known in the literature and can be achieved using methods known to a person skilled in the art (see S. P. H. Mee, V. Lee, J. E. Baldwin, Angew. Chem. Int. Ed., 2004, 43, 1 132-1 136.)
Figure imgf000217_0001
(IV) (XIII) l-A)
Pd catalyst
8) Compounds of formula (ΙΠ-Α) can be prepared by reacting a compound of formula (XIII) wherein X1 and X are leaving groups, for example a halogen, such as bromo, with a compound of formula (IV), wherein R13 is CrC6alkyl, using the same methods as described in 7).
Figure imgf000217_0002
9) Compounds of formula (I-A) can be prepared by reacting a compound of formula (XIV) wherein X1 is a leaving group, for example a halogen, such as bromo, with acompound of formula (IV), wherein R13 is CrC6alkyl, using the same methods as described in 7).
Scheme 7
Figure imgf000217_0003
(iii-A) (I.A)
10) Compounds of formula (I-A) can be prepared by reacting a compound of formula (ΙΠΑ) wherein X is a leaving group, for example a halogen, such as bromo, with carbon monoxide and an amine of formula (X), in the presence of a catalyst, such as palladium(II) diacetate, a ligand, such as a phosphine ligand, such as tributylphosphine, and a base such as cesium carbonate, or diisopropylethylamine (Hunig's base). The reaction is carried out in a suitable solvent, such as toluene, at a temperature of from 50°C to 200°C, preferably from 100°C to 150°C, in particular at 115°C. The reaction is carried out at a pressure of from 50 to 200 bar, preferably from 100 to 150 bar, in particular at 120 bar. Sche
Figure imgf000218_0001
(l-A) (l-A)
11) Compounds of formula (I-A) can be made by treatment of a compound of formula (II -A) with a compound of formula (X) and a dehydrating reagent. Alternatively, carboxylic acid (Π-Α) is transformed to an activated derivative, such as an acid chloride, for instance by treatment with thionyl chloride, or a mixed anhydride, for instance by treatment with ethyl chloroformate, and the activated derivative is reacted with a compound of formula (X), optionally in the presence of a base, and in a suitable solvent, such as, for instance, tetrahydrofuran. The reaction is carried out at a temperature of from -120°C to +130°C, preferably from -100°C to 100°C.
12) Alternatively, compounds of formula (I-A) can be made from a compound of formula (II-B) wherein Rx is Ci-Ci5alkoxy by heating the ester and an amine of formula (X) together in a thermal process. Amines of formula (X) are known in the literature or can be prepared using methods known to a person skilled in the art.
13) Compounds of formula (Π-Α), can be made by treatment of a compound of formula (III -A), wherein X is a halogen, for instance bromine, with a metallating agent, such as a metal, for instance magnesium, or an organometallic compound, for instance butyllithium, followed by the treatment with carbon dioxide. The reaction is carried out at a temperature of from -120°C to +130°C, preferably from - 100°C to 100°C.
14) Compounds of formula (IT A) can be made by hydrolysis of a compound of formula (Π-Β), and Rx is Ci-Ci5alkyl, such as methyl or teri-butyl. For instance, in the case where Rx is methyl or ethyl, the hydrolysis can be done with water and a base, such as potassium hydroxide, in the absence or in the presence of a solvent, such as, for instance, tetrahydrofuran or methynol. In the case where Rx is, for example, teri-butyl, the hydrolysis is done in the presence of acid, such as trifluoroacetic acid or hydrochloric acid. The reaction is carried out at a temperature of from -120°C to +130°C, preferably from -100°C to 100°C.
15) Compounds of formula (ITB) wherein Rx is Ci-Ci5alkoxy, can be prepared by reacting a compound of formula (ΙΠ-Α) wherein X is a leaving group, for example a halogen, such as bromo, with carbon monoxide and an alcohol of formula Rx-OH, such as ethanol, in the presence of a catalyst, such as bis(triphenylphosphine)palladium(II) dichloride, and a base, such as pyridine, triethylamine, 4- (dimethylamino)-pyridine ("DMAP") or diisopropylethylamine (Hunig 's base). The reaction is carried out at a temperature of from 50°C to 200°C, preferably from 100°C to 150°C, in particular at 1 15°C. The reaction is carried out at a pressure of from 50 to 200 bar, preferably from 100 to 150 bar, in particular at 120 bar.
Scheme 9
Figure imgf000219_0001
(XVI I I) (XIX)
16) 2,3-Dihydrofuran compounds of formula (XIX) wherein Px is P as defined in the claims (an amide or heterocycle), a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, may be prepared by isomerisation of 2,5-dihydrofuran of formula (XVIII) wherein Px is P as defined in the claims, a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, using a metal catalyst such as RhCl(PPh3)3, RhH(PPh3)4, H2Ru(CO)(PPh3)3, HClRu(CO)(PPh3)3 or H2Ru(PPh3)4 in a solvent such as toluene or an alcoholic solvent such as ethanol at a temperature of between room temperature and 150°C, preferably between 80°C and 120°C. Such conditions of isomerisation of 2,5-dihydrofuran compounds have been described in Chem. Eur. J. 2003, 9, 4442-4451 using the general catalytic isomerisation described by M. Mori et al in J. Org. Chem. 2000, 65, 3966-3970 or M. Bartok et al in J. Organomet. Chem. 1985, 297, C37-C40.
Alternatively, the isomerisation may be performed in the presence of basic oxide metal catalysts such as MgO, CaO, SrO, or La203 as described by K. Tanabe in Chem. Lett. 1981, 341 -342 for the isomerisation of 2,5-dihydrofuran.
Scheme 10
Figure imgf000220_0001
17) Compounds of formula (XXIII) can be prepared by hydrative cyclisation of a compound of formula (XXII) These reactions are usually carried out in the presence of a suitable lewis acid, such as a gold catalyst, as described in J. Am. Chem. Soc., 2010, 132 (10), pp 3258-3259. The reaction is usually carried out using (Triphenylphosphine)gold(I) bis(trifluoromethanesulfonyl)imidate, in the presence of a pyridine N-oxyde, such as 5-Bromo-l -oxy-nicotinic acid methyl ester and an acid, such as
methanesulfonic acid, in an aprotic solvent, such as 1 ,2-dichloroethane. The reaction is carried out at a temperature of from 0°C to 100°C, preferably from 0°C to 40°C.
18) Compounds of formula (XXII) can be prepared by reacting a compound of formula (XX) with a compound of formula (XXI), where X is a halogen. These reactions are usually carried out in the presence of a metal, such as magnesium, lithium, indium, cerium or zinc, in a suitable solvent, such as tetrahydrofuran, diethyl ether or N, N-dimethylformamide. The reaction is carried out at a temperature of from -78°C to 100°C, preferably from -78°C to ambient temperature. Alternatively, Compounds of formula (XXII) can be prepared by reacting a compound of formula (XX) with a compound of formula (XXI), where X is a trialkylsilyl group. These reactions are usually carried out in the presence of strong base, such as lithium diisopropylamide, in a suitable solvent, such as tetrahydrofuran, diethyl ether or N, N-dimethylformamide. The reaction is carried out at a temperature of from -78°C to 100°C, preferably from -78°C to ambient temperature.
Scheme 11
Figure imgf000220_0002
(XXV)
19) Compounds of formula (XVIII) and (XIX) wherein Px is P as defined in the claims, a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, can be prepared by reacting a compound of formula (XXIV) wherein X1 is a leaving group, for example a halogen, such as iodo or bromo and wherein Px is P as defined in the claims, a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, with a compound of formula (XXIII), in the presence of a metal, such as catalyst, such as magnesium, lithium, indium, cerium or zinc, in a suitable solvent, such as tetrahydrofuran, diethyl ether or N, N-dimethylformamide. The reaction is carried out at a temperature of from -78°C to 100°C, preferably from -78°C to ambient temperature.
20) Compounds of formula (XXV) can be prepared by reacting a compound of formula (XXIV) wherein X1 is a leaving group, for example a halogen, such as iodo or bromo, and wherein Px is P as defined in the claims, a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, with a compound of formula (XXIII), in the presence of a metal, such as magnesium, indium, cerium, zinc, or an organolithium reagent, such as n-butyl lithium, in a suitable solvent, such as tetrahydrofuran, diethyl ether or N, N-dimethylformamide. The reaction is carried out at a temperature of from -100°C to 100°C, preferably from -100°C to ambient temperature.
21) Compounds of formula (XVIII) and (XIX) wherein Px is P as defined in the claims, a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, can be prepared by reacting a compound of formula (XXV) wherein Px is P as defined in the claims, a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, in the presence of an acid, such as p-toluenesulfonic acid or sulphuric acid, or in the presence of a dehydrating agent, such as POCl3 in a suitable solvent, such as tetrahydrofuran, diethyl ether or dichloromethane. The reaction is carried out at a temperature of from -78°C to 100°C, preferably from -40°C to ambient temperature.
Alternatively, compounds of formula (XVIII) and (XIX) wherein Px is P as defined in the claims, a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Q- Ci5alkoxy, can be prepared by reacting a compound of formula (XXV) wherein Px is P as defined in the claims, a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Cr Ci5alkoxy, in the presence of a chlorinating agent, such as thionyl chloride or oxalyl chloride, or an acetylating agent, such as acetic anhydride in the presence of a base, such as triethylamine, potassium carbonate or pyridine, in a suitable solvent, such as tetrahydrofuran, diethyl ether or dichloromethane. The reaction is carried out at a temperature of from -78°C to 100°C, preferably from -40°C to ambient temperature.
Figure imgf000221_0001
22) Compounds of formula (XVIII) (and compounds of formula (XIX)) wherein Px is P as defined in the claims, a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or 22Q
Ci-Ci5alkoxy, can be prepared by reacting a compound of formula (XXVI) (and respectively compounds of formula (XXVII)) wherein X is a leaving group, for example a halogen, such as bromo, or a triflate, with a compound of formula (XXIV) wherein Px is P as defined in the claims, a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, wherein X1 is a boron derivative, such as a boronic acid, a pinacolboronate, or a trifluoroborate salt, in a Suzuki coupling reaction, in the presence of a palladium catalyst, such as palladium acetate or tetrakis(triphenylphosphine) palladium, in a suitable solvent, such as 1 ,4-dioxane, touene, acetonitrile or N, N-dimethylformamide. The reaction is carried out at a temperature of from -20°C to 150°C, preferably from ambient temperature to 100°C. Alternatively, compounds of formula (XVIII) (and compounds of formula (XIX)) wherein Px is P as defined in the claims, a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, can be prepared by reacting a compound of formula (XXVI) (and respectively compounds of formula (XXVII)) wherein X is a leaving group, for example a halogen, such as bromo, or a triflate and wherein Px is P as defined in the claims, a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, with a compound of formula (XXIV) wherein X1 is a trialkylstannane derivative, such as tributyltin, or respectively an organozinc derivative in a Stille or Negishi coupling reaction, in the presence of a palladium catalyst, such as palladium acetate or tetrakis(triphenylphosphine) palladium, in a suitable solvent, such as 1 ,4- dioxane, touene, acetonitrile or N, N-dimethylformamide.
23) Compounds of formula (XXVI) (and compounds of formula (XXVII)) wherein X is a halogen, such as bromo, can be prepared by reacting a compound of formula (XXIII) with a brominating agent, such as phosphoric tribromide, in a suitable solvent, such as tetrahydrofuran, or chloroform,
dichloromethane. The reaction is carried out at a temperature of from -40°C to 100°C, preferably from - 40°C to ambient temperature. Alternatively, compounds of formula (XXVI) (and compounds of formula (XXVII)) wherein X is a triflate, can be prepared by reacting a compound of formula (XXIII) with a triflating agent, such as triflic anhydride or N,N-bis(trifluoromethanesulfonyl)aniline, in the presence of a base, such as 4-picoline, sodium or potassium hexamethyldisilylamide, lithium diisopropylamide, triethylamine or 2,6-lutidine in a suitable solvent, such as tetrahydrofuran, chloroform or
dichloromethane. The reaction is carried out at a temperature of from -100°C to 150°C, preferably from - 40°C to 100°C.
Scheme 13
Figure imgf000222_0001
(XXVI II)
(XIX)
24) Compounds of formula (XIX) wherein Px is P as defined in the claims, a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, can be prepared by reacting a compound of formula (XXVIII) wherein Px is P as defined in the claims, a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, with trimethylsilyldiazomethane, in the presence of an organometallic reagent, such as methyl lithium, in a suitable solvent, such as tetrahydrofuran, diethyl ether, N, N-dimethylformamide or dimethoxy ethane. The reaction is carried out at a temperature of from -78°C to 100°C, preferably from -78°C to ambient temperature.
Figure imgf000223_0001
(XXIV)
25) Compounds of formula (XXX) can be prepared by reaction a compound of formula (XXIV), wherein X1 is an halogen, such as bromo or iodo, or a boron derivative, such as a boronic acid, a pinacol boronate or a trifluoroboronate salt and wherein Px is P as defined in the claims, a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, with a compound of formula (XXXI), wherein Rx is Ci-Ci5alkoxy (or with compounds of formula (XXIX)). The reaction is usually carried out in the presence of a palladium or rhodium catalyst, such as palladium acetate, in the presence of a ligand, such as triphenylphosphine, tricyclohexylphosphine or tri(tert- butyl)phosphine, and of an acid, such as acetic acid, or formic acid. These reactions are usually carried out in the presence of a suitable solvent, such as toluene, dichloromethane or chlorobenzene. The reaction is carried out at a temperature of from -78°C to 150°C, preferably from 0°C to 100°C.
26) Compounds of formula (XXXI), wherein Rx is Ci-Ci5alkoxy, can be made by transforming a compound of formula (XXIX) into an activated derivative, such as an acid chloride, for instance by treatment with thionyl chloride, or a mixed anhydride, for instance by treatment with ethyl chloroformate, and the activated derivative is reacted with a an alcohol, of formula RxOH, optionally in the presence of a base, and in a suitable solvent, such as, for instance, tetrahydrofuran. The reaction is carried out at a temperature of from -120°C to +130°C, preferably from -100°C to 100°C.
27) Compounds of formula (XXIX) can be made by oxidizing a compound of formula (XVI) into a carboxylic acid, using an oxidizing agent, such as a chromium derivative, and in a suitable solvent, such as, for instance, dichloromethane. The reaction is carried out at a temperature of from -120°C to +130°C, preferably from -100°C to 100°C. Such oxidations of alcohols into carboxylic acids are known in the literature and can be achieved using methods known to a person skilled in the art. Scheme 15
Figure imgf000224_0001
(XXXVI) (XXVI) (XIX)
28) Compounds of formula (XXVI) when X is a boron derivative, e.g. boronic acid, a
pinacolboronate or a trifluoroborate salt, can be prepared from compounds of formula (XXXVI) (e.g. prepared according to 47) or by ring closing metathesis, as in Journal of Organic Chemistry (2004), 69(22), 7672-7687, or using methods known by a person skilled in the art, such as in Chemistry-A European Journal, 7(11), 2349-2369; 2001) using a diboron derivative, such as pinacol diborane, in the presence of a suitable catalyst, such as iridium, in the presence of a suitable ligand, such as 4,4'-Di-tert- butylbipyridine as is described for example in Chemistry-An Asian Journal (2008), 3(12), 2082-2090. 29) Compounds of formula (XIX) can be prepared from compounds of formula (XXIV) and (XXVI) when X is a boron derivative and X1 is a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, using a Suzuki reaction, e.g. as descibed in 22).
30) Compounds of formula (XXVI) when X is tin derivative, e.g. SnR13 3 wherein R13 is Ci-C6alkyl , e.g. tributyltin, can be prepared from compounds of formula (XXXVI) using a trialkyltin hydride as is described for example in Journal of Organic Chemistry, 69(1), 72-78; 2004.
31) Compounds of formula (XIX) can be prepared from compounds of formula (XXIV) and (XXVI) when X is a tin derivative and X1 is a leaving group, for example a halogen, such as bromo, using the methods described in 7).
Figure imgf000225_0001
(XXXIX) deprotection deprotection
Figure imgf000225_0002
(XXVII)
(XVI) (XXXX)
Pd catalyst
Figure imgf000225_0003
(XXIV)
Figure imgf000225_0004
(XVI II)
32) Compounds of formula (XXVII) when X is a boron derivative, e.g. boronic acid, a
pinacolboronate or a trifluoroborate salt, can be prepared from compounds of formula (XXXX ) as is described in 6) .
33) Compounds of formula (XVIII) can be prepared from compounds of formula (XXIV) and (XXVII) when X is a boron derivative and X1 is a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, using a Suzuki reaction, e.g. as descibed in 22).
34) Compounds of formula (XXXX) when X is a boron derivative, e.g. boronic acid, a
pinacolboronate or a trifluoroborate salt, can be prepared by treating a compounds of formula (XVI) with a borane derivative, such as pinacol borane or catecholborane in a suitable solvent such as tetrahydrofuran or dichloromethane. Alternatively, Compounds of formula (XXXX) when X is a boron derivative, e.g. boronic acid, a pinacolboronate or a trifluoroborate salt, can be prepared by treating a compounds of formula (XVI) with a diboron derivative, such as pinacol diborane, in the presence of a suitable catalyst, such as copper, palladium of nickel, as is described for example in Chemical Communications, 2008, 6, 733-734 and Angewandte Chemie, International Edition, 47(52), 10183-10186; 2008.
Methodology suitable for the preparation of compounds of formula (XXXX) when X is a boron derivative, e.g. boronic acid, a pinacolboronate or a trifluoroborate salt, from compounds of formula (XXXIX) when X is a boron derivative, e.g. boronic acid, a pinacolboronate or a trifluoroborate salt, is described in Schemes 1) Scheme 17
Figure imgf000226_0001
35) Compounds of formula (XXXVIII) where X is boron derivative can be prepared from compounds of formula (XXXI) (see scheme 14) using the same procedure as is described in scheme 2) using a borane derivative, such as pinacol borane or catecholborane in a suitable solvent such as tetrahydrofuran or dichloromethane, in the presence of a copper hydride, e.g. as is described in Angewandte Chemie, International Edition (2008), 47(52), 10183-10186. Alternatively, compounds of formula (XXXVIII) when X is a boron derivative, can be prepared from compounds of formula (XXXI) using the same procedure as is described in scheme 2) using a diboron derivative, such as pinacol diborane, in the presence of a suitable catalyst, such as copper, palladium of nickel, as is described for example in Angewandte Chemie, International Edition (2009), 48(12), 2192-2195.
36) Compounds of formula (XXX) can be prepared from compounds of formula (XXIV) and (XXXVIII) when X is a boron derivative and X1 is a leaving group for example a halogen, such as bromo, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, using a Suzuki reaction, e.g. as described in 22). 37) Compounds of formula (XXXVIII) where X is a tin derivative can be prepared from compounds of formula (XXXI) (see scheme 14) using the same procedure as is described in 2), e.g. using a trialkyltin hydride compound of formula (IX) in the presence of a palladium catalyst, or a copper catalyst, as is described in Organic Letters (2005), 7(23), 5249-5252.
38) Compounds of formula (XXX) can be prepared from compounds of formula (XXIV) and (XXXVIII) when X is a tin derivative and X1 is a leaving group, for example a halogen, such as bromo, using the methods described in 7).
Scheme 18
Figure imgf000227_0001
Pd catalyst, CO
H O - RX
metallation, then CO5
(XV)
Figure imgf000227_0002
(XXXIV) (XXXIII)
Figure imgf000227_0003
(l-B) (l-B)
39) Compounds of formula (I-B) can be made by treatment of a compound of formula (XXXIV) with a compound of formula (X) using the same methods as described in 11).
40) Alternatively, compounds of formula (I-B) can be made from a compound of formula (XXXIII) wherein Rx is CpCealkoxy by heating the ester and an amine of formula (X) together in a thermal process. Amines of formula (X) are known in the literature or can be prepared using methods known to a person skilled in the art.
41) Compounds of formula (XXXIV), can be made by treatment of a compound of formula (XXXII), wherein X is a halogen, for instance bromine, using the same methods as described in 13).
42) Compounds of formula (XXXIV) can be made by hydrolysis of a compound of formula
(XXXIII), and Rx is CpCealkyl, such as methyl or teri-butyl using the same methods as described in 14).
43) Compounds of formula (XXXIII) wherein Rx is CpCealkoxy, can be prepared by reacting a compound of formula (XXXII) wherein X is a leaving group, for example a halogen, such as bromo, with an alcohol of formula Rx-OH, using the same methods as described in 15). Scheme
Figure imgf000228_0001
base, catalyst
(XXXII) (XXXV)
44) Compounds of formula (XXXV), wherein Pn is an optionally substituted heterocycle, can be made, for example in the case where the heterocycle is attached via a nitrogen atom, by treatment of a compound (XXXII) wherein X is a halogen, such as fluorine, with a heterocyclic compound Pn-H and a suitable base, such as potassium carbonate. Alternatively, compounds of formula (XXXV), wherein Pn is an optionally substituted heterocycle, can be made, for example in the case where the heterocycle is attached via a carbon atom, by treatment of a compound (XXXII) wherein X is a halogen, such as bromine, with a heterocyclic compound Pn-M, wherein M is hydrogen or a metal, such as boron, magnesium or zinc, in which case M can be optionally substituted, with a base and a suitable catalyst, such as a palladium or a copper catalyst, in the presence of a suitable ligand for the catalyst, such as, for example, a diamine ligand, or a phosphine ligand. Such reactions are carried out at a temperature of from -120°C to +130°C, preferably from -100°C to 100°C.
45) The compounds of formula (IA) can be obtained from racemic mixtures by chiral separation using HPLC.
In the above descriptions reference to leaving groups includes leaving groups such as halogen, Ci-Cgalkoxy, Ci-Cgalkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, CpCgarylsulfonyloxy, optionally substituted CpCgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g. the leaving group may be selected from -N2 + CI", -N2 + BF4 ", -N2 + Br", -N2 + PF6 _) and phosphonate esters (e.g. -OP(0)(OR)¾ wherein R is methyl or ethyl).
Scheme 20
Figure imgf000228_0002
(XIX)
(XXVI)
In scheme 20 Ar stands for group A
Figure imgf000229_0001
(A)
wherein A1, A2, A3, A4 are as defined for compounds of formula (IA) and Px is as defined for compounds of formula (XIX). In scheme 20 X stands for a halogen (X = CI, Br, I); M stands for a derivative of B, Si, Sn, Mg, Zn, Mn.
46) Compounds of formula LII can be obtained from compounds of formula LI via hydroformylation, e.g. by reacting compounds of formula LI with CO and H2 in the presence of a suitable catalyst. Structure LII comprises any composition of cyclic stereo-isomers and or of open chain structure Lllb isomers.
Suitable catalysts for the hydroformylation reaction are complexes of transition metals (rhodium, cobalt, platinum, palladium, iridium) preferably rhodium, preferably with a suitable ligand. Particularly preferred ligands include hydride, carbonyl, halogen, substituted and unsubstituted cyclopentadienyls, 2,4-alkanedionates (e.g. acetyacetonate), phosphorus derivatives and mixtures thereof. Phosphorus derivatives are preferred and are typically represented by the formula P(R)3 wherein R is an aryl, alkyl, alkoxy, aryloxy, alkylamino, arylamino or a bidentate ligand of the formula (R)2P-Y-P(R)2, Y represents a 1 -20 atom linker. Each R groups may be the same or different.
Preferred ligands are monodentate and bidentate phospines, phosphites, phosphinites. Preferred specific ligands are e.g. triphenyl phosphine, triphenyl phosphite, BIPHEPHOS (2,2'-Bis[(l,l'-biphenyl- 2,2'-diyl)phosphite]-3,3'-di-tert-butyl-5,5'-dimethoxy-l,l'-biphenyl), 6-DPPon (6-(diphenylphosphino)- 2(lH)-pyridinone), BISBI (2,2'-Bis[(diphenylphosphino)methyl]-l,l'-biphenyl), NAPHOS (2,2'- Bis(diphenylphosphinomethyl)-l,l'-binaphthalene), XANTPHOS (9,9-Dimethyl-4,5- bis(diphenylphosphino)xanthene), tBu-XANTPHOS (1,1 '-[2,7-bis(l , 1 -dimethylethyl)-9,9-dimethyl-9H- xanthene-4,5-diyl]bis[l,l-diphenylphosphine]), TPPTS (3,3',3"-phosphinidynetris[benzenesulfonic acid] trisodium salt), Tris(2,4-bis( 1 , 1 -dimethylethyl)phenyl)-phosphite.
The catalyst may be formed in situ from a catalyst precursor (such as acetylacetonato)dicarbonyl rhodium, tris(triphenylphosphine)rhodium carbonyl hydride, Rh6(CO) i6, RI12O3, RI1CI3, [Rh(OMe)COD]2, [Rh2(OAc)4], [RhCl(COD)]2) and a suitable ligands or preformed in a separate step. A preferred catalyst precursor to ligand ratio is between 1 : 1 to 1 : 100 more preferably between 1 :5 to 1 :50.
The reaction temperature is preferably in the range of 0-250°C more preferably at 50-150°C. The reaction pressure is preferably in the range of 1-200 bar more preferably 10-lOObar (an atmosphere of carbon monoxide and hydrogen). The reaction time is usually in the range lh to lOOh.
The molar ration of CO:H2 is preferably 1 : 100 to 100: 1 more preferably 1 :5 to 5: 1. Optionally,
CO and/or H2 reactants may be generated in situ from formaldehyde, formic acid derivates, metal carbonyls or other suitable precursors. 0
- ZZo -
Preferred solvents include C5-C2o aliphatic hydrocarbons, C6-C2o aromatic hydrocarbons, halogenated hydrocarbons, alcohols, ethers, esters, amides, and mixtures thereof.
47) Compounds of formula XXXVI may be prepared from compounds of formula LII by dehydration (elimination of water) in the presence of a suitable acidic catalyst or a suitable activation agent
(carboxylic or sulfonic acid chloride or anhydride) and a suitable base (Et3N, pyridine, DBU). The acid catalyst is preferably p-toluenesulfonic acid, methane sulfonic acid or pyridinium p-toluenesulfonate. Relative amount of the catalyst to substrate is preferably l -100mol%. The reaction may be further facilitated by the presence of a drying agent (Na2S04, molecular sieves), azeotropic distillation, gas flow through the reaction mixture, application of vacuum (vacuum distillation, flash vacuum pyrolysis) or other means of removing the water formed. Reaction temperature is in the range 0°C to 1000°C, more preferably 50°C to 200°C. Reaction pressure is preferably between 0.1 mbar and atmospheric, most between 0.1 to 200 mbar. The reaction time is usually in the range O.lh to lOOh. The product of the hydroformylation reaction LII may be isolated and or purified before the dehydratation or alternatively the conversion to XXXVI may be carried in the same pot as the hydroformylation reaction (one pot reaction).
48) Compounds of formula LIII may be prepared from compounds of formula VXXXVI by reacting compounds of formula VI with a halogen X (X represents CI, Br, I). Structure LIII comprises any composition of cyclic stereo-isomers. Suitable solvents include polar and non-polar organic solvents e.g. dichloromethane, chloroform, dichloroethane, dioxane, ethyl acetate, acetonitrile, THF. The reaction temperature is usually in the range -78°C to 100°C, more preferably -78°C to 0°C. The reaction time is usually in the range O.lh to lOOh.
49) Compounds of formula XXVI, may be prepared from compounds of formula LIII by elimination of HXC, preferably in the presence of a suitable base and solvent. Suitable bases include Et3N, diisopropyl ethyl amine, pyridine, DBU, DBM, iPrMgCl, iPrMgBr, LDA. Suitable solvents include polar and non- polar organic solvents e.g. dichloroethane, dioxane, THF, toluene, DMF, NMP, acetonitrile. The reaction temperature is usually in the range -30°C to 200°C, more preferably 0°C to 150°C. The reaction time is usually in the range O.lh to lOOh.
50) Compounds of formula XIX can be obtained from compounds of formula LIII via a coupling reaction (e.g. Suzuki, Stille , Hiyama, Kumada, Negishi) e.g. by treating compounds of formula VII, with a reactant Ar-M, wherein Ar are as defined above and M represents a suitable derivative of B, Si, Sn, Mg, Zn, Mn (e.g. boronic acid, boronic ester, trifluoroborate, dialkyl-hydroxysilane, trialkyltin, MgCl, MgBr, ZnCl, ZnBr, MnCl) in presence of a catalyst and optionally in the presence of a suitable ligand, solvent and additive. Suitable catalysts are e.g. palladium catalysts such as Pd(OAc)2, PdCl2, Pd2(dba)3,
Pd2(dba)3.CHCl3, [Pd(PPh3)4], [Pd(Cl)2(H3CCN)2)], [(allyl)Pd(Cl)]2, [Pd(PPh3)2(Cl)2], [Pd(DPPF)(Cl)2], PEPPSI, nickel catalysts such as NiCl2, Ni(OAc)2, Ni(acac)2, [Ni(PPh3)2Cl2], [Ni(DPPP)Cl2] . Suitable ligands are e.g. phosphine ligands such as P(tBu)3, tris(ortho-tolyl)phosphine, ΒΓΝΑΡ, PPh3, PCy3, S- Phos, X-Phos, Ru-Phos, trifuryl phosphine, Tris(2,4-bis(l,l-dimethylethyl)phenyl)-phosphite, DPEphos, Josiphos and carbine ligands such as IMes, SIMes, IPr, SIPr. Suitable solvents include polar and non- polar organic solvents e.g. DMF, DMA, DME, dioxane, NMP, toluene, xylene, water, AcCN, THF, ionic liquids. Suitable additives are e.g. trialkyl amine, metal carbonate or acetate or phosphate or fluoride. Examples of additives are e.g. Et3N, Na2C03, K2CO3, CS2CO3, K3PO4, KF, CsF. The reaction temperature is usually in the range 0°C to 200°C, more preferably 50°C to 150°C. The reaction time is usually in the range lh to lOOh.
Scheme 21
Figure imgf000231_0001
(XXII*)
(LIV*
In scheme 21 Ar stands for group A
Figure imgf000231_0002
(A)
wherein A1, A2, A3, A4 are as defined for compounds of formula (IA) and Px is as defined for compounds of formula (XIX). In scheme 21 XD represents a halogen (CI, Br, I) or a pseudohalogen (OTf, OTs, diazonium).
51) Compounds of formula LIV can be obtained from the corresponding aryl halide via a coupling reaction (e.g. Suzuki, Stille , Hiyama, Kumada, Negishi, Sonigashira) e.g. by treating the Ar-XD , wherein Ar are as defined above and XD represents a halogen (CI, Br, I) or a pseudohalogen (OTf, OTs, diazonium) with an ethynyl-M, wherein Ar are as defined above and M represents a suitable derivative of B, Si, Sn, Mg, Zn, Cu (formed in situ from corresponding terminal alkyne) in presence of a catalyst and 23Q optionally in the presence of a suitable ligand, solvent and additive. Suitable catalysts are e.g. palladium catalysts such as Pd(OAc)2, PdCl2, Pd2(dba)3, Pd2(dba)3.CHCl3, [Pd(PPh3)4], [Pd(Cl)2(H3CCN)2)], [(allyl)Pd(Cl)]2, [Pd(PPh3)2(Cl)2], [Pd(DPPF)(Cl)2], PEPPSI, Suitable solvents include polar and non- polar organic solvents e.g. DMF, DMA, DME, dioxane, NMP, toluene, xylene, water, AcCN, THF, ionic liquids. Suitable additives are e.g. trialkyl amine, metal carbonate or acetate or phosphate or fluoride. Examples of additives are e.g. Et3N, Na2C03, K2C03, Cs2C03, K3P04, KF, CsF. The reaction temperature is usually in the range 0°C to 200°C, more preferably 50°C to 150°C. The reaction time is usually in the range lh to lOOh.
52) Enantiomerically enriched compounds of formula LV** wherein R3 and R4 are as defined for compounds of formula I and wherein Ar are as defined above can be prepared by deprotonating compounds of formula LIV using a suitable base in a suitable aprotic organic solvent between -90°C and 80°C, followed by reaction with a titanium alkoxide or chloroalkoxide e.g. Ti(OiPr)4, Ti(OEt)4, ClTi(OiPr)3 between -40°C and 60°C in the presence of chiral amino alcohols ligands or chiral diol ligands, a suitable additive and compounds of formula VII, as described in Angewandte Chemie, International Edition (2011), 50(15), 3538-3542. Suitable base are BuLi, sec -BuLi, tert-BuLi, Me2Zn, Et2Zn, Me3Al, Et3Al. Suitable solvents are xylenes, toluene, THF, DME, CH2C12, C2H4C12. The preffered solvent is toluene. Suitable chiral ligands are Cinchona alkaloids (e.g. quinine, quinidine, cinchonidine, cinchonine), N,N-dialkylephedrine, Ν,Ν-dialkylpseudoephedrine, (R)-binol, (R)-H8-binol. Preferred ligands are Cinchona alkaloids. Suitable additives are CaH2 and BaF2. The preferred reaction temperature is between -30°C and 30°C.
53) Enantiomerically enriched compounds of formula LV** wherein R3 and R4 are as defined for compounds of formula I and wherein Ar are as defined above can be prepared by deprotonating compounds of formula LIV using a suitable organolithium base e.g. BuLi between -100 and -40°C in an aprotic organic solvent (e.g. toluene, tetrahydrofuran, 1,2-dimethoxyethane, 1,4-dioxane, diethylether, CH2C12, C2H4C12) in presence of a chiral diol ligand (e.g. (S)-l -(2-hydroxy-3-phenyl-l-naphthyl)-3- phenyl-naphthalen-2-ol) and compounds of formula VII as described in Chem. Commun. 2011, 47, 5614.
54) Enantiomerically enriched compounds of formula LIX** wherein R3 and R4 are as defined for compounds of formula I and wherein Ar are as defined above can be obtained by reduction of compounds of LV** by sodium bis(2-methoxyethoxy)aluminumhydride as described in Tetrahedron, 66(39), 7726- 7731 ; 2010. Suitable solvents for this reaction are toluene, tetrahydrofuran, 1,2-dimethoxyethane, 1,4- dioxane and diethylether. The reaction is run between -78°C and 25°C and preferably between -50°C and -10°C.
55) Enantiomerically enriched compounds of formula LVI** wherein R3 and R4 are as defined for compounds of formula I and wherein Ar are as defined above can be obtained by reduction of compounds of LV** by deactivated palladium catalysts (e.g. Lindlar's catalyst) as described in Tetrahedron, 53(11), 3879-3916; 1997. The suitable solvents for this reaction are ethyl acetate, tetrahydrofuran, 1,2- dimethoxyethane, 1,4-dioxane, diethylether, methanol and ethanol. The reaction is run between -0°C and 100°C and preferably between 10 and 60°C. ^ 1
56) Compounds of formula XXII wherein R3 and R4 are as defined for compounds of formula I can be prepared by addition of ethynylnucleophiles (e.g. ethynylmagnesium bromide, ethynylmagnesium chloride) to the ketone of formula VII, e.g. using similar conditions as described in Advanced Synthesis & Catalysis, 349(8+9), 1393-1398; 2007.
57) Compounds of formula LVIII wherein R3 and R4 are as defined for compounds of formula I and R14 is Ci-Ci2alkyl, preferably Ci-Cg alkyl, are prepared by reacting compounds of formula XXII using similar conditions as described in Advanced Synthesis & Catalysis, 349(8+9), 1393-1398; 2007.
58) Enantiomerically enriched compounds of formula XXII* and LVIII** wherein R3 and R4 are as defined for compounds of formula I and R14 is
Figure imgf000233_0001
preferably Ci-Cg alkyl are prepared by treating compounds of formula LVIII with a suitable hydrolase enzyme in a suitable aqueous system in presence of a suitable buffer, pH 5-9, between 10°C and 80°C. Suitable enzymes are Pig liver esterase (Roche), Novozyme 398 (Novozymes), Novozymes 435 (supported lipase, Novozymes), Alcalase from Bacillus licheniformis (Merck), Alcalase (Novozymes), Protease type XIII from Aspergillus oryzae (Sigma), Lipase from Candida rugosa (Sigma), Lipase type VII from Candida rugosa (Sigma), Palatase, lipase from Rhizomucor miehei (Sigma), Wheat germ lipase (Sigma), Lipase PS from Burkholderia cepacia (Amano), Lipase AK from Pseudomonas fluorescens (Amano), Lipase from porcine pancreas (Sigma), Esterase ECS-Es 01 (Enzymicals), Esterase ECS-Es 06 (Enzymicals), Esterase ECS-Es 08 (Enzymicals), Esterase ECS-Es 09 (Enzymicals), Esterase ECS-Es 10 (Enzymicals), Lipase MY from Candida rugosa (Meito Sangyo), Lipase OF from Candida rugosa (Meito Sangyo), Lipase SL from Burkholderia cepacia (Meito Sangyo), Lipase TL from Pseudomonas stutzeri (Meito Sangyo). The preferred enzymes are Lipase from Candida rugosa (Sigma), Lipase type VII from Candida rugosa (Sigma), Lipase MY from Candida rugosa (Meito Sangyo), Lipase OF from Candida rugosa (Meito Sangyo). The suitable solvents systems are water, water/dimethylsulfoxide, water/toluene, water/acetone, water/methanol,
water/acetonitrile, water/1, 4-dioxane, water/n-hexane, water/cyclohexane, water/methyl -tert-butylether, water/diisopropylether. The preferred solvent systems are water/dimethylsulfoxide, water/methanol, water/acetone, water/n-hexane, water/cyclohexane. The preferred buffers are NaH2P04/Na2HP04 and KH2PO4/K2HPO4. The preferred pH is 7.4. The preferred temperature is between 35 and 55°C.
59) Enantiomerically enriched compounds of formula LVII** a wherein R3 and R4 are as defined for compounds of formula I and R14 is Ci-Cnalkyl, preferably Ci-Cg alkyl are prepared by treating compounds of formula LVIII with a suitable hydrolase enzyme in a suitable aqueous system in presence of a suitable buffer, pH 5-9, between 10°C and 80°C. Preferred enzymes are Lipase QLM from
Alcaligenes sp. (Meito Sangyo) and Lipase PL from Alcaligenes sp. (Meito Sangyo). The preferred solvent systems are water/dimethylsulfoxide, water/methanol, water/acetone, water/n-hexane, water/cyclohexane. The preferred buffers are NaH2P04/Na2HP04 and KH2PO4/K2HPO4. The preferred pH is 7.4. The preferred temperature is between 35 and 55°C.
60) Enantiomerically enriched compounds of formula LIX** wherein R3 and R4 are as defined for compounds of formula I and wherein PG is an organosilicon, preferably trialkylsilyl and most preferably trimethylsilyl, are prepared by deprotonation of ethynyl-PG with a suitable organolithium (e.g. BuLi) in ^ presence of a suitable chiral modifier, preferably aminoalcohols ligand in a aprotic organic solvent between -80°C and 25°C. The preferred chiral ligand are dialkylephedrine and dialkylpseudoephedrine. The most preferred chiral ligand is (lR,2S)-l -phenyl-2-pyrrolidin-l-yl-propan-l -ol. The preferred solvent is tetrahydrofuran. The preffered temperature is between -70°C and 20°C.
61) Enantiomerically enriched compounds of formula LVII** wherein R3 and R4 are as defined for compounds of formula I are prepared by reactions of compounds of formula LIX** wherein PG is an organosilicon, preferably trialkylsilyl and most preferably trimethylsilyl, with a suitable base or fluorine source in a suitable organic solvent. Preferred bases are tetrabutylammionium fluoride, potassium carbonate and sodium carbonate. Preferred solvent are tetrahydrofuran, ethanol and methanol. Suitable reaction temperatures is between -10°C and 60°C.
62) Enantiomerically enriched compounds of formula LIV** wherein R3 and R4 are as defined for compounds of formula I can be obtained by reduction of compounds of LVII** by deactivated palladium catalysts (e.g. Lindlar's catalyst) as described in Tetrahedron, 53(11), 3879-3916; 1997. The suitable solvents for this reaction are ethyl acetate, tetrahydrofuran, 1,2-dimethoxyethane, 1,4-dioxane, diethylether, methanol and ethanol. The reaction is run between -0°C and 100°C and preferably between 10 and 60°C.
63) Enantiomerically enriched compounds of formula LIV* wherein R3 and R4 are as defined for compounds of formula I can be obtained by reduction of compounds of XXII* by deactivated palladium catalysts (e.g. Lindlar's catalyst) as described in Tetrahedron, 53(11), 3879-3916; 1997. The suitable solvents for this reaction are ethyl acetate, tetrahydrofuran, 1,2-dimethoxyethane, 1,4-dioxane, diethylether, methanol and ethanol. The reaction is run between -0°C and 100°C and preferably between 10 and 60°C.
Scheme 22
Figure imgf000235_0001
(Lvr)
In scheme 22 Ar stands for group A
Figure imgf000235_0002
(A)
wherein A1, A2, A3, A4 are as defined in the claims and Px is as defined for compounds of formula (XIX). 64) Compounds of formula LX**, wherein Ar is as defined above and wherein R3 and R4 are as defined for compounds of formula (IA), may be prepared via hydroformylation of compounds of formula LIX** or LVI**, e.g. by reacting compounds of formula LIX** with CO and H2 in the presence of a suitable catalyst. Structure LX** comprises any composition of cyclic stereo-isomers and or of open chain structure LXb** isomers.
Suitable catalysts for the hydroformylation reaction are complexes of transition metals (rhodium, cobalt, platinum, palladium, iridium) preferably rhodium, preferably with a suitable ligand. Particularly preferred ligands include hydride, carbonyl, halogen, substituted and unsubstituted cyclopentadienyls, 2,4-alkanedionates (e.g. acetylacetonate), phosphorus derivatives and mixtures thereof. Phosphorus derivatives are preferred and are typically represented by the formula P(R)3 wherein R is an aryl, alkyl, alkoxy, aryloxy, alkylamino, arylamino or a bidentate ligand of the formula (R)2P-Y-P(R)2, Y represents a 1 -20 atom linker. Each R groups may be the same or different.
Preferred ligands are bulky, π-acceptor phosphines, phosphites, phosphinite, phosphabenzenes, phosphabarrelenes, PArxR3.x (x = 0-2; R = pyrrolyl, indolyl, carbazolyl; Ar = aryl, e.g. phenyl), preferably ^ phosphites, phosphabenzenes, phosphinolines and phosphaadamantanes. Preferred specific ligands are e.g. Triphenyl phosphite, BIPHEPHOS, tris(hexafluoroisopropyl) phosphite, Tris(2,4-bis(l , l - dimethylethyl)phenyl)-phosphite, Tris(2-(1 , 1 -dimethylethyl)phenyl)-phosphite, Tris(2-(1 , 1 - dimethylethyl)-4-methyl-phenyl)-phosphite, 2,4,6-Triphenylphosphabenzene, 2,3,4,5,6- pentaphenylphosphabenzene,
2,3,5,6-tetraphenylphosphabenzene, 2,6-bis(2,4-dimethylphenyl)-4-phenylphosphabenzene,
2,6-bis(2-methylphenyl)-4-phenylphosphabenzene, 4-phenyl-2,6- bis(2,4,5trimethylphenyl)phosphabenzene, 2,6-di-2-naphthalenyl-4-phenylphosphabenzene, 2-(2- naphthalenyl)-4,6-diphenylphosphabenzene, 2,6-bis(l -methylethyl)-4-phenylphosphabenzene, 2,4,6- tris( 1 , 1 -dimethylethyl)phosphabenzene, 2,6-dimethyl-4-phenylphosphabenzene, 2,4, 10-triphenyl-4H-l ,4- ethenophosphinoline, 2, 10-bis(l -methylethyl)-4-phenyl-4H- 1 ,4-ethenophosphinoline, 2, 10-bis(2,4- dimethylphenyl)-4-phenyl-4H-l ,4-ethenophosphinoline, 2,10-bis(2,4-dimethylphenyl)-6-methyl-4- phenyl-4H-l ,4-ethenophosphinoline, 2, 10-bis(2,4-dimethylphenyl)-7-methyl-4-phenyl-4H- 1 ,4- ethenophosphinoline, 1 ,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane, 1 ,3,5,7-tetraethyl- 6-phenyl-2,4,8-trioxa-6-phosphaadamantane.
The catalyst may be formed in situ from a catalyst precursor (such as (acetylacetonato)dicarbonyl rhodium, tris(triphenylphosphine)rhodium carbonyl hydride, Rh6(CO)i6, Rh203, RhCl3, [Rh(OMe)COD]2, [Rh2(OAc)4], [RhCl(COD)]2) and a suitable ligands or preformed in a separate step. A preferred catalyst precursor to ligand ratio is between 1 : 1 to 1 : 100 more preferably between 1 :5 to 1 :50.
The reaction temperature is preferably in the range of 0-250°C more preferably at 50-150°C. The reaction pressure is preferably in the range of 1 -200 bar more preferably 10-l OObar (an atmosphere of carbon monoxide and hydrogen). The reaction time is usually in the range lh to l OOh.
The molar ration of CO:H2 is preferably 1 : 100 to 100: 1 more preferably 1 :5 to 5: 1. Optionally, CO and/or H2 reactants may be generated in situ from formaldehyde, formic acid derivatives, metal carbonyls or other suitable precursors.
Preferred solvents include C5-C20 aliphatic hydrocarbons, C6-C20 aromatic hydrocarbons, halogenated hydrocarbons, alcohols, ethers, esters, amides, and mixtures thereof. For liquid substrates the reaction may be performed neat.
65) Compounds of formula (XIX), wherein Ar is as defined above and wherein R3 and R4 are as defined for compounds of formula (IA), may be prepared from compounds of formula LX** by dehydration (elimination of water) in the presence of a suitable acidic catalyst or a suitable activation agent (carboxylic or sulfonic acid chloride or anhydride) and a suitable base (Et3N, pyridine, DBU). The acid catalyst is preferably p-toluenesulfonic acid or pyridinium p-toluenesulfonate. Relative amount of the catalyst to substrate is preferably 1 -1 OOmol % more preferably 1 : 10-30mol%. The reaction may be further facilitated by the presence of a drying agent (Na2SO (, molecular sieves), azeotropic distillation, gas flow through the reaction mixture, application of vacuum or other means of removing the water formed.
Reaction temperature is in the range 0°C to 200°C, more preferably 50°C to 150°C. Reaction pressure is preferably between 0.1 mbar and atmospheric, most preferably atmospheric. The reaction time is usually in the range lh to lOOh. The product of the hydroformylation reaction LX** may be isolated and or purified before the dehydratation or alternatively the conversion to (I) may be carried in the same pot as the hydroformylation reaction (one pot reaction).
Hydroformation reactions, including reaction conditions and suitable catalylst, are described in Breit et al., Chem.Comm., 2004, 694-695, Fuchs et al., Chem. Eur. J., 2006, 12, 6930-6939, and Breit et al., Chem. Eur. J., 2001, 7, No. 14, each of which is incorporated by reference.
Scheme 23
Figure imgf000237_0001
(LIX**)
Figure imgf000237_0002
(LVI**)
(XIX**)
Figure imgf000237_0003
(LVII**)
66) Compounds of formula XIX** may be prepared from compounds of formula LIX**, LVI** and LVII** following the procedures set out above.
The reaction described above are also applicable to synthesis of racemic mixtures.
In a further aspect the invention provides a process for preparing a compound of formula (XIX)
Figure imgf000237_0004
wherein
Ar is group A
Figure imgf000237_0005
(A)
R3, R4, A1, A2, A3, A4 are as defined for the compound of formula (IA), and Px is P as defined for the compound of formula (IA), a leaving group XB, such as halogen, Ci-Cgalkoxy, Ci-Cgalkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, Q-Cgarylsulfonyloxy, optionally substituted Q-Cgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g. XB is -N2 + CI", -N2 + BF4 ", -N2 + Br", -N2 + PF6 "), phosphonate esters (e.g. -OP(0)(OR)2; wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, or a salt or N-oxide thereof;
comprising dehydrating a compound of formula (LX)
Figure imgf000238_0001
wherein R3, R4 and Ar are as defined for the compound of formula (XIX);
with a suitable acidic catalyst or a suitable activation agent and a suitable base. Examples of preferred reaction conditions are described in paragraph 65.
The compound of formula (LX) may be prepared by reacting a compound of formula (LIX) or
(LVI)
Figure imgf000238_0002
wherein R3, R4 and Ar are as defined for the compound of formula (XIX);
with a source of H2 and CO in the presence of a catalyst comprising a complex of a transition metal and a suitable ligand. Examples of preferred reaction conditions are described in paragraph 64.
In a further aspect the invention provides a process for the preparation of a compound of formula (LX) comprising reacting a compound of formula (LIX) with a source of H2 and CO in the presence of a catalyst comprising a complex of a transition metal and a suitable ligand. Examples of preferred reaction conditions are described in paragraph 64.
In particular, the complex of a transition metal is preferably a rhodium complex and the ligand is preferably a phosphite, phosphabenzene, phosphinoline or phosphaadamantane ligand. The source of hydrogen and CO reactants may be gaseous CO and/or H2 or generated in situ e.g. from formaldehyde, formic acid derivates, metal carbonyls or other suitable precursors.
In a further aspect the invention provides a process for the preparation of a compound of formula
(XXXVI)
Figure imgf000238_0003
(xxxvi)
wherein R3 and R4 are as defined for the compound of formula (IA) comprising dehydrating a compound of formula (LII)
Figure imgf000239_0001
with a suitable acidic catalyst or a suitable activation agent and a suitable base. Examples of preferred reaction conditions are described in paragraph 47.
The compound of formula (LII) may be prepared by reacting a compound of formula (LI)
Figure imgf000239_0002
with a source of H2 and CO in the presence of a catalyst comprising a complex of a transition metal and a suitable ligand. Examples of preferred reaction conditions are described in paragraph 46.
The reaction may include the additional step of reacting the compound of formula (XXXVI) with chlorine, bromine or iodine to give a compound of formula (LIII)
Figure imgf000239_0003
wherein R and R are as defined for the compound of formula (XIX) and each X is independently CI, Br or I. Examples of preferred reaction conditions are described in paragraph 48.
The reaction may include the additional step of eliminating HX from the compound o formula (LIII) e.g. in the presence of a suitable base, to give a compound of compound of formula (XXVI)
Figure imgf000239_0004
wherein RJ and R4 are as defined for the compound of formula (IA) and X is CI, Br or I. Examples of preferred reaction conditions are described in paragraph 49.
The reaction may also include the additional step of reacting a compound of formula (XXVI) with a compound of formula Ar-M, wherein Ar is group A
Figure imgf000239_0005
(A)
wherin A1, A2, A3, A4 are as defined for the compound of formula (IA), and Px is P as defined for the compound of formula (IA), a leaving group, such as halogen, Q-Cgalkoxy, Ci-C8alkylsulfonyloxy, Cr Cghaloalkylsulfonyloxy, Ci-C8arylsulfonyloxy, optionally substituted Q-Cgarylsulfonyloxy (aryl is - ο - preferably phenyl), diazonium salts (e.g. XB is -N2 + CI", -N2 + BF4 ", -N2 + Br", -N2 + PF6 "), phosphonate esters (e.g. -OP(0)(OR)2; wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy;
to give a compound of formula
Figure imgf000240_0001
wherein R3 and R4 are as defined for the compound of formula (IA) and Ar is as defined above. Examples of preferred reaction conditions are described in paragraph 50.
In a further aspect the invention provides a process for the preparation of a compound of formula (LII) comprising reacting a compound of formula (LI) with a source of H2 and CO in the presence of a catalyst comprising a complex of a transition metal and a suitable ligand. Examples of preferred reaction conditions are described in paragraph 46.
The complex of a transition metal is preferably a rhodium complex and the ligand is preferably a phosphite, phosphabenzene, phosphinoline or phosphaadamantane ligand. The source of hydrogen and CO reactants may be gaseous CO and/or H2 or generated in situ e.g. from formaldehyde, formic acid derivates, metal carbonyls or other suitable precursors.
Intermediates useful in this process are also form additional aspects of the invention.
Accordingly, a group of novel intermediates are compounds of formula (LX)
Figure imgf000240_0002
(LX)
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) and Px is P as defined for the compound of formula (IA), a leaving group XB, such as halogen, Q-Cgalkoxy, Cp
Cgalkylsulfonyloxy, Ci-Cghaloalkylsulfonyloxy, Ci-Cgarylsulfonyloxy, optionally substituted Cp Cgarylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g. XB is -N2 + CI", -N2 + BF4 ", -N2 + Br", - N2 + PF6 "), phosphonate esters (e.g. -OP(0)(OR)2; wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, or a salt or N-oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 and Px
(when Px is P) are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
One group of compounds of formula (LX) are compounds of (LXa)
Figure imgf000241_0001
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) and XB is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
Another group of compounds of formula (LX) are compounds of (LXb)
Figure imgf000241_0002
wherein R1, R2, R3, R4 , A1, A2, A3 and A4 are as defined for the compound of formula (IA), or a salt or N-oxide thereof. The preferences for R1, R2, R3, R4, A1, A2, A3, A4 are the same as the preferences set our for the corresponding substituents of the compound of formula (IA) .
Another group of compounds of formula (LX) are compounds of (LXc)
Figure imgf000241_0003
(LXc)
wherein A1, A2, A3, A4, R3 and R4 are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula I. The preferences for A1, A2, A3, A4, R3, R4 and heterocyclyl are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
Another group of novel intermediates are compounds of formula (LIX)
Figure imgf000241_0004
(LIX) 24Q wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) and Px is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 and Px (when Px is P) are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
One group of compounds of formula (LIX) are compounds of (LIXa)
Figure imgf000242_0001
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) and XB is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
Another group of compounds of formula (LIX) are compounds of (LIXb)
Figure imgf000242_0002
wherein R1, R2, R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA), or a salt or N- oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA).
Another group of compounds of formula (LIX) are compounds of (LIXc)
Figure imgf000242_0003
(LIXc)
wherein A1, A2, A3, A4, R3 and R4 are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula (IA). The preferences for A1, A2, A3, A4, R3, R4 and heterocyclyl are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
Another group of novel intermediates are compounds of formula (LII)
Figure imgf000243_0001
wherein R and R are as defined for compounds of formula (IA), or a salt or N-oxide thereof. The preferences for R3 and R4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
Another group of novel intermediates are compounds of formula (LIII)
Figure imgf000243_0002
wherein R3 and R4 are as defined for compounds of formula (IA), and X represents CI, Br or I, or a salt or N-oxide thereof. The preferences for R3 and R4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
Another group of novel intermediates are compounds of formula (XXVI)
Figure imgf000243_0003
wherein R3 and R4 are as defined for the compound of formula (IA) and X is CI, Br or I, or a salt or N- oxide thereof. The preferences for R3 and R4 are the same as the preferences set our for the corresponding substituents of the compound of formula (IA) .
Another group of novel intermediates are com ounds of formula (XXXVI)
Figure imgf000243_0004
(xxxvi)
wherein R3 and R4 are as defined for the compound of formula (IA). The preferences for R3 and R4 are the same as the preferences set our for the corresponding substituents of the compound of formula (IA), or a salt or N-oxide thereof.
Another group of novel intermediates are compounds of formula (LI)
Figure imgf000243_0005
(LI) wherein R and R are as defined for the compound of formula (IA), or a salt or N-oxide thereof. The preferences for R3 and R4 are the same as the preferences set our for the corresponding substituents of the compound of formula (IA) .
Additional intermediates are useful in the preparation of compounds as racemic mixtures of e.g. formula (LIX), and these compounds form additional aspects of the invention.
Another group of novel intermediates are compounds of formula (LV)
Figure imgf000244_0001
(LV)
wherein R3, R4 , A1, A2, A3 and A4 are as defined for compounds of formula (IA) and Px is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 and Px (when Px is P) are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
One group of compounds of formula (LV) are compounds of (LVa)
Figure imgf000244_0002
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) and XB is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA) .
Another group of compounds of formula (LVA) are compounds of (LVb)
Figure imgf000245_0001
wherein R1, R2, R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA), or a salt or N- oxide thereof. The preferences for R3, R4, A1, A2, A3, A4 are the same as the preferences set out for the corresponding substituents of the compound of formula (IA).
Another group of compounds of formula (LV) are compounds of (LVc)
Figure imgf000245_0002
(LVc)
wherein A1, A2, A3, A4, R3 and R4 are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula I. The preferences for A1, A2, A3, A4, R3, R4 and heterocyclyl are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The invention also provides compounds of formula (LVI)
Figure imgf000245_0003
wherein R3, R4 , A1, A2, A3 and A4 are as defined for compounds of formula (IA) and Px is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4 , A1, A2, A3, A4 and Px (when Px is P) are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
One group of compounds of formula (LVI) are compounds of (LVIa) wherein R3, R4 , A1, A2, A3 and
Figure imgf000246_0001
(IA) and XB is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R3, R4 , A1, A2, A3, A4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
Another group of compounds of formula (LVI) are compounds of (LVlb)
Figure imgf000246_0002
wherein R1, R2, R3, R4 , A1, A2, A3 and A4 are as defined for compounds of formula (IA) and X is as defined for the compound of formula (XXVA), or a salt or N-oxide thereof. The preferences for R1, R2, R3, R4 , A1, A2, A3, A4 are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
Another group of compounds of formula (LVI) are compounds of (LVlc)
Figure imgf000246_0003
wherein A1, A2, A3, A4, R3 and R4 are as defined for the compounds of formula (IA), and Pn is a heterocyclyl or heteocyclyl substituted by one to five Z, as defined for compounds of formula I. The preferences for A1, A2, A3, A4, R3, R4 and heterocyclyl are the same as the preferences set out for the corresponding substituents of a compound of formula (IA).
The compounds of formula (IA) can be used to combat and control infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera,
Siphonaptera, Hymenoptera and Isoptera and also other invertebrate pests, for example, acarine, nematode and mollusc pests. Insects, acarines, nematodes and molluscs are hereinafter collectively referred to as pests. The pests which may be combated and controlled by the use of the compounsd of the invention include those pests associated with agriculture (which term includes the growing of crops for food and fiber products), horticulture and animal husbandry, companion animals, forestry and the storage of products of vegetable origin (such as fruit, grain and timber); those pests associated with the damage of ^ man-made structures and the transmission of diseases of man and animals; and also nuisance pests (such as flies). The compounds of the invention may be used for example on turf, ornamentals, such as flowers, shrubs, broad-leaved trees or evergreens, for example conifers, as well as for tree injection, pest management and the like. Compositions comprising the compound of formula (IA) may be used on ornamental garden plants (e.g. flowers, shrubs, broad-leaved trees or evergreens), e.g. to control aphids, whitefly, scales, meelybug, beetles and caterpillars. Compositions comprising the compound of formula (IA) may be used on garden plants (e.g. flowers, shrubs, broad-leaved trees or evergreens), on indoor plants (e.g. flowers and shrubs) and on indoor pest e.g. to control aphids, whitefly, scales, meelybug, beetles and caterpillars.
Furthermore, the compounds of the invention may be effective against harmful insects, without substantially imposing any harmful side effects to cultivated plants. Application of the compounds of the invention may increase the harvest yields, and may improve the quality of the harvested material. The compounds of the invention may have favourable properties with respect to amount appled, residue formulation, selectivity, toxicity, production methodology, high activity, wide spectrum of control, safety, control of resistant organisms, e.g. pests that are resistant to organic phosphorus agents and/or carbamate agents.
Examples of pest species which may be controlled by the compounds of formula (IA) include: coleopterans, for example, Callosobruchus chinensis, Sitophilus zeamais, Tribolium castaneum,
Epilachna vigintioctomaculata, Agriotes fuscicollis, Anomala rufocuprea, Leptinotarsa decemlineata, Diabrotica spp., Monochamus alternatus, Lissorhoptrus oryzophilus, Lyctus bruneus, Aulacophora femoralis; lepidopterans, for example, Lymantria dispar, Malacosoma neustria), Pieris rapae,
Spodoptera litura, Mamestra brassicae, Chilo suppressalis), Pyrausta nubilalis, Ephestia cautella, Adoxophyes orana, Carpocapsa pomonella, Agrotisfucosa, Galleria mellonella, Plutella maculipennis, Heliothis virescens, Phyllocnistis citrella; hemipterans, for example, Nephotettix cincticeps, Nilaparvata lugens, Pseudococcus comstocki, Unaspis yanonensis, Myzus persicas, Aphis pomi, Aphis gossypii,
Rhopalosiphum pseudobrassicas, Stephanitis nashi, Nezara spp., Trialeurodes vaporariorm, Psylla spp.; thysanopterans, for example, Thrips palmi, Franklinella occidental; orthopterans, for example, Blatella germanica, Periplaneta americana, Gryllotalpa Africana, Locusta migratoria migratoriodes ; isopterans, for example, Reticulitermes speratus, Coptotermes formosanus; dipterans, for example, Musca domestica, Aedes aegypti, Hylemia platura, Culex pipiens, Anopheles sinensis, Culex tritaeniorhynchus, Liriomyza trifolii; acari, for example, Tetranychus cinnabarinus, Tetranychus urticae, Panonychus citri, Aculops pelekassi, Tarsonemus spp. ; nematodes, for example, Meloidogyne incognita, Bursaphelenchus lignicolus Mamiya et Kiyohara, Aphelenchoides besseyi, Heterodera glycines, Pratylenchus spp..
Examples of further pest species which may be controlled by the compounds of formula (IA) include: from the order of the Anoplura (Phthiraptera), for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.; from the class of the Arachnida, for example, Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., . . ,
- 246 -
Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici; from the class of the Bivalva, for example, Dreissena spp.; from the order of the Chilopoda, for example, Geophilus spp., Scutigera spp.; from the order of the Coleoptera, for example,
Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator,
Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna
consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., PopilUa japonica, Premnotrypes spp., PsylUodes chrysocephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp.; from the order of the Collembola, for example, Onychiurus armatus; from the order of the Dermaptera, for example, Forficula auricularia; from the order of the Diplopoda, for example, Blaniulus guttulatus; from the order of the Diptera, for example, Aedes spp., Anopheles spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia spp., Cochliomyia spp.,
Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fannia spp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanus spp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.; from the class of the Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.; from the class of the helminths, for example,
Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti; ft may be furthermore possible to control protozoa, such as Eimeria; from the order of the Heteroptera, for ^ example, Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp.,
Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.; from the order of the Homoptera, for example, Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp.,
Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola,
Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, MonelUopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp.,
Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii; from the order of the
Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Mono- morium pharaonis, Vespa spp.; from the order of the Isopoda, for example, Armadillidium vulgar e, Oniscus asellus, Porcellio scaber; from the order of the Isoptera, for example, Reticulitermes spp., Odontotermes spp.; from the order of the Lepidoptera, for example, Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp., Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella, Laphygma spp.,
Lithocolletis blancardella, Lithophane antennata, Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestra brassicae, Mods repanda, Mythimna separata, Oria spp., Oulema oryzae, Panolis - 4ο - flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp.; from the order of the
Orthoptera, for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria; from the order of the Siphonaptera, for example, Ceratophyllus spp., Xenopsylla cheopis. From the order of the Symphyla, for example, Scutigerella immaculata; from the order of the Thysanoptera, for example, Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.; from the order of the Thysanura, for example, Lepisma saccharina. The phytoparasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp.,
Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp.,
Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.
In particular, the compounds of the invention may be used to control the following pest spcies:
Myzus persicae (aphid), Aphis gossypii (aphid), Aphis fabae (aphid), Lygus spp. (capsids), Dysdercus spp. (capsids), Nilaparvata lugens (planthopper), Nephotettixc incticeps (leafhopper), Nezara spp. (stinkbugs), Euschistus spp. (stinkbugs), Leptocorisa spp. (stinkbugs), Frankliniella occidentalis (thrip), Thrips spp. (thrips), Leptinotarsa decemlineata (Colorado potato beetle), Anthonomus grandis (boll weevil), Aonidiella spp. (scale insects), Trialeurodes spp. (white flies), Bemisia tabaci (white fly), Ostrinia nubilalis (European corn borer), Spodoptera littoralis (cotton leafworm), Heliothis virescens (tobacco budworm), Helicoverpa armigera (cotton bollworm), Helicoverpa zea (cotton bollworm), Sylepta derogata (cotton leaf roller), Pieris brassicae (white butterfly), Plutella xylostella (diamond back moth), Agrotis spp. (cutworms), Chilo suppressalis (rice stem borer), Locusta migratoria (locust), Chortiocetes terminifera (locust), Diabrotica spp. (rootworms), Panonychus ulmi (European red mite), Panonychus citri (citrus red mite), Tetranychus urticae (two-spotted spider mite), Tetranychus cinnabarinus (carmine spider mite), Phyllocoptruta oleivora (citrus rust mite), Polyphagotarsonemus latus (broad mite), Brevipalpus spp. (flat mites), Boophilus microplus (cattle tick), Dermacentor variabilis (American dog tick), Ctenocephalides felis (cat flea), Liriomyza spp. (leafminer), Musca domestica (housefly), Aedes aegypti (mosquito), Anopheles spp. (mosquitoes), Culex spp. (mosquitoes), Lucillia spp. (blowflies), Blattella germanica (cockroach), Periplaneta americana (cockroach), Blatta orientalis (cockroach), termites of the Mastotermitidae (for example Mastotermes spp.), the
Kalotermitidae (for example Neotermes spp.), the Rhinotermitidae (for example Coptotermes formosanus, Reticulitermes flavipes, R. speratu, R. virginicus, R. hesperus, and R. santonensis) and the Termitidae (for example Globitermes sulfureus), Solenopsis geminata (fire ant), Monomorium pharaonis (pharaoh's ant), Damalinia spp. and Linognathus spp. (biting and sucking lice), Meloidogyne spp. (root knot nematodes), Globodera spp. and Heterodera spp. (cyst nematodes), Pratylenchus spp. (lesion nematodes),
Rhodopholus spp. (banana burrowing nematodes), Tylenchulus spp. (citrus nematodes), Haemonchus contortus (barber pole worm), Caenorhabditis
Figure imgf000251_0001
eelworm), Trichostrongylus spp. (gastro intestinal nematodes) and Deroceras reticulatum (slug).
The compound of formula (IA) may be used for pest control on various plants, including soybean (e.g. in some cases 10-70g/ha), corn (e.g. in some cases 10-70g/ha), sugarcane (e.g. in some cases 20- 5 200g/ha), alfalfa (e.g. in some cases 10-70g/ha), brassicas (e.g. in some cases 10-50g/ha), oilseed rape (e.g. canola) (e.g. in some cases 20-70g/ha), potatoes (including sweet potatoes) (e.g. in some cases 10- 70g/ha), cotton (e.g. in some cases 10-70g/ha), rice (e.g. in some cases 10-70g/ha), coffee (e.g. in some cases 30-150g/ha), citrus (e.g. in some cases 60-200g/ha), almonds (e.g. in some cases 40-180g/ha), fruiting vegetables, cucurbits and pulses (e.g. tomatoes, pepper, chili, eggplant, cucumber, squash etc.)0 (e.g. in some cases 10-80g/ha), tea (e.g. in some cases 20-150g/ha), bulb vegetables (e.g. onion, leek etc.) (e.g. in some cases 30-90g/ha), grapes (e.g. in some cases 30-180g/ha), pome fruit (e.g. apples, pears etc.) (e.g. in some cases 30-180g/ha), and stone fruit (e.g. pears, plums etc.) (e.g. in some cases 30-180g/ha).
The compounds of the invention may be used for pest control on various plants, including soybean, corn, sugarcane, alfalfa, brassicas, oilseed rape (e.g. canola), potatoes (including sweet 5 potatoes), cotton, rice, coffee, citrus, almonds, fruiting vegetables, cucurbits and pulses (e.g. tomatoes, pepper, chili, eggplant, cucumber, squash etc.), tea, bulb vegetables (e.g. onion, leek etc.), grapes, pome fruit (e.g. apples, pears etc.), stone fruit (e.g. pears, plums etc.), and cereals.
The compounds of the invention may be used on soybean to control, for example, Elasmopalpus Ugnosellus, Diloboderus abderus, Diabrotica speciosa, Trialeurodes spp., Bemisia spp., aphids,0 Sternechus subsignatus, Formicidae, Agrotis ypsilon, Julus spp., Murgantia spp., Halyomorpha spp., Thyanta spp., Megascelis ssp., Procornitermes ssp., Gryllotalpidae, Nezara viridula, Piezodorus spp., Acrosternum spp., Neomegalotomus spp., Cerotoma trifurcata, PopilUa japonica, Edessa spp., Liogenys fuscus, stalk borer, Scaptocoris castanea, phyllophaga spp., Migdolus spp., Pseudoplusia includens, Anticarsia gemmatalis, Epinotia spp., Rachiplusia spp., Spodoptera spp. (e.g. Spodoptera frugiperda),5 Bemisia tabaci, Tetranychus spp., Agriotes spp. , Euschistus spp. (e.g. Euschistus hews). The compounds of the invention are preferably used on soybean to control Diloboderus abderus, Diabrotica speciosa, Trialeurodes spp., Bemisia spp., Nezara viridula, Piezodorus spp., Acrosternum spp., Cerotoma trifurcata, PopilUa japonica, Euschistus hews, Scaptocoris castanea, phyllophaga spp., Migdolus spp., Agriotes spp., Euschistus spp..
0 The compounds of the invention may be used on corn to control, for example, Euschistus spp.
(e.g. Euschistus hews), Dichelops furcatus, Diloboderus abderus, Thyanta spp., Elasmopalpus
Ugnosellus, Halyomorpha spp., Spodoptera frugiperda, Nezara viridula, Cerotoma trifurcata, PopilUa japonica, Agrotis ypsilon, Diabrotica speciosa, aphids, Heteroptera, Procornitermes spp., Scaptocoris castanea, Formicidae, Julus ssp., Dalbulus maidis, Diabrotica spp. (e.g. Diabrotica virgifera), Mods5 latipes, Bemisia tabaci, heliothis spp., Tetranychus spp., thrips spp., phyllophaga spp., Migdolus spp., scaptocoris spp., Liogenys fuscus, Spodoptera spp., Ostrinia spp., Sesamia spp., wireworms, Agriotes spp., Halotydeus destructor. The compounds of the invention are preferably used on corn to control Euschistus spp., (e.g. Euschistus hews), Dichelops furcatus, Diloboderus abderus, Nezara viridula, 25Q
Cerotoma trifurcata, Popillia japonica, Diabrotica spp. (e.g. Diabrotica speciosa, Diabrotica virgifera), Tetranychus spp., Thrips spp., Phyllophaga spp., Migdolus spp., Scaptocoris spp., Agriotes spp..
The compounds of the invention may be used on sugar cane to control, for example,
Sphenophorus spp., termites, Migdolus spp., Diloboderus spp., Telchin licus, Diatrea saccharalis, Mahanarva spp., Mealybugs, Chilo spp.
The compounds of the invention may be used on alfalfa to control, for example, Hypera brunneipennis, Hypera postica, Colias eurytheme, Collops spp., Empoasca solana, Epitrix spp., Geocoris spp., Lygus hesperus, Lygus Uneolaris, Spissistilus spp., Spodoptera spp., Aphids, Trichoplusia ni. The compounds of the invention are preferably used on alfalfa to control Hypera brunneipennis, Hypera postica, Empoasca solana, Epitrix spp., Lygus hesperus, Lygus Uneolaris, Trichoplusia ni.
The compounds of the invention may be used on brassicas to control, for example, Chrysodeixis spp., Plutella xylostella, Pieris spp. (e.g. Pieris brassicae, Pieris rapae, Pieris napi), Mamestra spp. (e.g. Mamestra brassicae), Plusia spp., Trichoplusia spp. (e.g. Trichoplusia ni), Phyllotreta spp. (e.g.
Phyllotreta cruciferae, Phyllotreta striolata), Spodoptera spp., Empoasca spp., thrips spp., Delia spp., Murgantia spp., Trialeurodes spp., Bemisia spp., Microtheca spp., Aphids, Chaetocnema spp., PsylUodes spp. (e.g. PsylUodes chrysocephala). The compounds of the invention are preferably used on brassicas to control Plutella xylostella, Pieris spp., Plusia spp., Trichoplusia ni, Phyllotreta spp., Thrips spp., Chaetocnema spp..
The compounds of the invention may be used on oil seed rape, e.g. canola, to control, for example, Meligethes spp. (e.g. Meligethes aeneus), Ceutorhynchus spp., (e.g. Ceutorhynchus assimilis,
Ceutorhynchus napi), Halotydeus destructor, Psylloides spp. (e.g. PsylUodes chrysocephala), Phyllotreta spp. (e.g. Phyllotreta cruciferae, Phyllotreta striolata), Chaetocnema spp..
The compounds of the invention may be used on potatoes, including sweet potatoes, to control, for example, Empoasca spp., Leptinotarsa spp., Diabrotica speciosa, Phthorimaea spp., Paratrioza spp., Maladera matrida, Agriotes spp., Aphids, wireworms. The compounds of the invention are preferably used on potatoes, including sweet potatoes, to control Empoasca spp., Leptinotarsa spp., Diabrotica speciosa, Phthorimaea spp., Paratrioza spp., Agriotes spp..
The compounds of the invention may be used on cotton to control, for example, Anthonomus grandis, Pectinophora spp., heliothis spp., Spodoptera spp., Tetranychus spp. (e.g. Tetranychus urticae), Empoasca spp., Thrips spp. (e.g. Thrips tabaci, Thrips palmi), Bemisia tabaci, Trialeurodes spp., Aphids,
Lygus spp. (e.g. Lygus Uneolaris, Lygus Hesperus), phyllophaga spp., Scaptocoris spp., Austroasca viridigrisea, Creontiades spp., Nezara spp., Piezodorus spp., Halotydeus destructor, Oxycaraenus hyalinipennis, Dysdercus cingulatus, Amrasca spp. ( e.g. Amrasca biguttula biguttula), Frankliniella spp.
(e.g. Frankliniella schultzei), Scirtothrips spp. (e.g. Scirtothrips dorsali), Anaphothrips spp.,
Polyphagotarsonemus latus. The compounds of the invention are preferably used on cotton to control
Anthonomus grandis, Tetranychus spp., Empoasca spp., thrips spp., Lygus spp., phyllophaga spp.,
Scaptocoris spp.. ^ ^
The compounds of the invention may be used on rice to control, for example, Leptocorisa spp. (e.g. Leptocorisa oratorius, Leptocorisa chinensis, Leptocorisa acuta), Cnaphalocrosis spp., Chilo spp. (e.g. Chilo suppressalis, Chilo polychrysus, Chilo auricilius), Scirpophaga spp. (e.g. Scirpophaga incertulas, Scirpophaga innotata, Scirpophaga nivella), Lissorhoptrus spp., Oebalus pugnax,
Scotinophara spp. (e.g. Scotinophara coarctata, Scotinophara lurida, Scotinophara latiuscula),
Nephotettix spp. (e.g. Nephotettix malayanus, Nephotettix nigropictus, Nephotettix parvus, Nephottetix virescens, Nephotettix cincticeps), Mealybugs, Sogatella furcifera, Nilaparvata lugens, OrseoUa spp. (e.g. OrseoUa oryzae), Cnaphalocrocis medinalis, Marasmia spp. (e.g. Marasmia patnalis, Marasmia exigua), Stenchaetothrips biformis, Thrips spp., Hydrellia spp. (e.g. Hydrellia philippina), Grasshoppers, Pomacea canaliculata, Scirpophaga innotata, Sesamia infer ens, Laodelphax striatellus, Nymphula depunctalis, Oulema oryzae, Stinkbugs. The compounds of the invention are preferably used on rice to control Leptocorisa spp., Lissorhoptrus spp., Oebalus pugnax, Nephotettix spp.(e.g. Nephotettix malayanus, Nephotettix nigropictus, Nephotettix parvus, Nephottetix virescens, Nephotettix cincticeps), Sogatella furcifera, Stenchaetothrips biformis, Thrips spp., Hydrellia spp. (e.g. Hydrellia philippina),
Grasshoppers, Pomacea canaliculata, Scirpophaga innotata, Chilo spp. , Oulema oryzae.
The compounds of the invention may be used on coffee to control, for example, Hypothenemus spp. (e.g. Hypothenemus Hampei), Perileucoptera Coffeella, Tetranychus spp., Brevipalpus spp., Mealybugs. The compounds of the invention are preferably used on coffee to control Hypothenemus Hampei, Perileucoptera Coffeella.
The compounds of the invention may be used on citrus to control, for example, Panonychus citri,
Phyllocoptruta oleivora, Brevipalpus spp. (e.g. Brevipalpus californicus, Brevipalpus phoenicis), Diaphorina citri, Scirtothrips spp. (e.g. Scirtothrips dorsalis), Thrips spp., Unaspis spp., Ceratitis capitata, Phyllocnistis spp. (e.g. Phyllocnistis citrella), Aphids, Hardscales, Softscales, Mealybugs. The compounds of the invention are preferably used on citrus to control Panonychus citri, Phyllocoptruta oleivora, Brevipalpus spp., Diaphorina citri, Scirtothrips spp., thrips spp., Phyllocnistis spp..
The compounds of the invention may be used on almonds to control, for example, Amyelois transitella, Tetranychus spp.
The compounds of the invention may be used on fruiting vegetables, cucurbits and pulses, including tomatoes, pepper, chili, eggplant, cucumber, squash etc., to control, for example, Thrips spp., Tetranychus spp. (e.g. Tetranychus urticae)., Polyphagotarsonemus spp. (e.g. Polyphagotarsonemus latus), Aculops spp. (e.g. Aculops lycopersici), Empoasca spp. (e.g. Empoasca fabae), Spodoptera spp., heliothis spp., Tuta absoluta, Liriomyza spp. (e.g. Liriomyza brassicae, Liriomyza bryoniae, Liriomyza huidobrensis, Liriomyza sativae, Liriomyza trifolii), Bemisia tabaci, Trialeurodes spp., Aphids,
Paratrioza spp., Frankliniella spp. (e.g. Frankliniella occidentalis, Frankliniella intonsa, Frankliniella bispinosa), Spodoptera spp. (e.g. Spodoptera exigua, Spodoptera littoralis, Spodoptera litura, Spodoptera frugiperda, Spodoptera eridania), Anthonomus spp., Phyllotreta spp., Amrasca spp. (e.g. Amrasca biguttula biguttula), Epilachna spp., Halyomorpha spp., Scirtothrips spp., Leucinodes spp. (e.g.
Leucinodes orbonalis), Neoleucinodes spp. (e.g. Neoleucinodes elegantalis) , Maruca spp., Fruit flies, Stinkbugs, Lepidopteras, Coleopteras, Helicoverpa spp. (e.g. Helicoverpa armigera), Heliothis spp. (e.g. Heliothis virescens), Paratrioza spp. (e.g. Paratrioza cockerelli), The compounds of the invention are preferably used on fruiting vegetables, cucurbits and pulses, including tomatoes, pepper, chili, eggplant, cucumber, squash etc., to control Thrips spp., Tetranychus spp., Polyphagotarsonemus spp., Aculops spp., Empoasca spp., Spodoptera spp., heliothis spp., Tuta absoluta, Liriomyza spp., Paratrioza spp.,
Frankliniella occidentalis, Frankliniella spp., Amrasca spp., Scirtothrips spp., Leucinodes spp.,
Neoleucinodes spp..
The compounds of the invention may be used on tea to control, for example, Pseudaulacaspis spp., Empoasca spp., Scirtothrips spp., Caloptilia theivora, Tetranychus spp..T e compounds of the invention are preferably used on tea to control Empoasca spp., Scirtothrips spp..
The compounds of the invention may be used on bulb vegetables, including onion, leek etc. to control, for example, Thrips spp., Spodoptera spp., heliothis spp.. The compounds of the invention are preferably used on bulb vegetables, including onion, leek etc. to control Thrips spp..
The compounds of the invention may be used on grapes to control, for example, Empoasca spp., Lobesia spp., Eupoecilia ambiguella, Frankliniella spp., Thrips spp., Tetranychus spp., Rhipiphorothrips Cruentatus, Eotetranychus Willamettei, Erythroneura Elegantula, Scaphoides spp., Scelodonta strigicollis, Mealybugs. The compounds of the invention are preferably used on grapes to control Frankliniella spp., Thrips spp., Tetranychus spp., Rhipiphorothrips Cruentatus, Scaphoides spp..
The compounds of the invention may be used on pome fruit, including apples, pears etc., to control, for example, Cacopsylla spp., Psylla spp., Panonychus ulmi, Cydia pomonella, Lepidopteras, Aphids, Hardscales, Softscales. The compounds of the invention are preferably used on pome fruit, including apples, pears etc., to control Cacopsylla spp., Psylla spp., Panonychus ulmi.
The compounds of the invention may be used on stone fruit to control, for example, Grapholita molesta, Scirtothrips spp., Thrips spp., Frankliniella spp., Tetranychus spp., Aphids, Hardscales, Softscales, Mealybugs. The compounds of the invention are preferably used on stone fruit to control Scirtothrips spp., Thrips spp., Frankliniella spp., Tetranychus spp..
The compounds of the invention may be used on cereals to control, for example, Aphids, Stinkbugs, earthmites, Eurygaster integriceps, Zabrus tenebrioides, Anisoplia austriaca, Chaetocnema aridula, Phyllotreta spp., Oulema melanopus, Oscinella spp., Delia spp., Mayetiola spp., Contarinia spp., Cephus spp., Steneotarsonemus spp., Apamea spp..
In another embodiment compounds of formula (IA) and mixtures of the invention may be used on rice to control Baliothrips biformis (Thrips), Chilo spp. (e.g. Chilo polychrysus (Dark headed striped borer), Chilo suppressalis (Rice stemborer), Chilo indicus (Paddy stem borer), Chilo polychrysus (Dark- headed rice borer), Chilo suppressalis (Stripe stem borer)), Cnaphalocrocis medinalis (Rice leaf folder), Dicladispa armigera (Hispa), Hydrellia philipina (Rice whorl-maggot), Laodelphax spp. (Smaller brown planthopper) (e.g. Laodelphax striatellus ), Lema oryzae (Rice leafbeetle), Leptocorsia acuta (Rice bug), Leptocorsia oratorius (rice bug), Lissorhoptrus oryzophilus (rice water weevil), Mythemina separata (armyworm), Nephottetix spp. (Green leafhopper ) (e.g. Nephotettix cincticeps, Nephotettix malayanus, ^
Nephotettix nigropictus, Nephotettix parvus, Nephottetix virescens), Nilaparvata lugens (Brown
Planthopper), Nymphula depunctalis (Rice caseworm), Orseolia oryzae (Rice Gall midge), Oulema oryzae (Rice leaf eetle), Scirpophaga incertulas (Yellow Stemborer), Scirpophaga innotata (White Stemborer), Scotinophara coarctata (Rice black bug), Sogaella frucifera (White -backed planthopper), Steneotarsonemus spinki.
The compounds of the invention may be used to control animal housing pests including: Ants, Bedbugs (adult), Bees, Beetles, Boxelder Bugs, Carpenter Bees, Carpet Beetles, Centipedes, Cigarette, Beetles, Clover Mites, Cockroaches, Confused Flour Beetle, Crickets, Earwigs, Firebrats, Fleas, Flies, Lesser Grain Borers, Millipedes, Mosquitoes, Red Flour Beetles, Rice Weevils, Saw-toothed Grain Beetles, Silverfish, Sowbugs, Spiders, Termites, Ticks, Wasps, Cockroaches, Crickets, Flies, Litter Beetles (such as Darkling, Hide, and Carrion), Mosquitoes, Pillbugs, Scorpions, Spiders, Spider Mites (Twospotted, Spruce), Ticks.
The compounds of the invention may be used to control ornamental pests including: Ants (Including Imported fire ants), Armyworms, Azalea caterpillars, Aphids, Bagworms, Black vine weevils (adult), Boxelder bugs, Budworms, California oakworms, Cankerworms, Cockroaches, Crickets,
Cutworms, Eastern tent caterpillars, Elm leaf beetles, European sawflies, Fall web worms, Flea beetles, Forest tent caterpillars, Gypsy moth larvae, Japanese beetles (adults), June beetles (adults), Lace bugs, Leaf- feeding caterpillars, Leafhoppers, Leafminers (adults), Leaf rollers, Leaf skeletonizers, Midges, Mosquitoes, Oleander moth larvae, Pillbugs, Pine sawflies, Pine shoot beetles, Pinetip moths, Plant bugs, Root weevils, Sawflies, Scale insects (crawlers), Spiders, Spittlebugs, Striped beetles, Striped oakworms, Thrips, Tip moths, Tussock moth larvae, Wasps, Broadmites, Brown softscales, California redscales (crawlers), Clover mites, Mealybugs, Pineneedlescales (crawlers), Spider mites, Whiteflies
The compounds of the invention may be used to control turf pests including: Ants (Including Imported fire ants, Armyworms, Centipedes, Crickets, Cutworms, Earwigs, Fleas (adult), Grasshoppers, Japanese beetles (adult), Millipedes, Mites, Mosquitoes (adult), Pillbugs, Sod webworms, Sow bugs, Ticks (including species which transmit Lyme disease), Bluegrass billbugs (adult), Black turfgrass ataenius (adult), Chiggers, Fleas (adult), Grubs (suppression), Hyperodes weevils (adult), Mole crickets (nymphs and young adults), Mole Crickets (mature adults), Chinch Bugs.
The compounds of formula (IA) and mixture of the invention, in particular those in the tables above, may be used for soil applications, including as a seed application, to target at least the following: sucking pests such as aphids, thrips, brown plant hopper (e.g. on rice), sting bugs, white flies (e.g. on cotton and vegetables), mites; on soil pests such as corn root worm, wireworms, white grubs, zabrus, termites (e.g. on sugar cane, soy, pasture), maggots, cabbage root fly, red legged earth mite; on lepidoptera, such as spodoptera, cutworms, elasmoplpus, plutella (e.g. brassica), stem borers, leaf miners, flea beetle, Sternechus; on nematicides, such as Heterodera glycines (e.g. on soybean), Pratylenchus brachyurus (e.g. on corn), P. zeae (e.g. oncorn), P. penetrans (e.g. on corn), Meloidogyne incognita (e.g. on vegetables), Heterodera schachtii (e.g. on sugar beet), Rotylenchus reniformis (e.g. on cotton), Heterodera avenae (e.g. on cereals), Pratylenchus neglectus (e.g. on cereals), thornei (e.g. on cereals). ^
The compounds of formula (IA) and mixture of the invention, in particular those in the tables above may be used for seed applications at least on the following: soil grubs for corn, soybeans, sugarcane: Migdolus spp; Phyllophaga spp.; Diloboderus spp; Cyclocephala spp; Lyogenys fuscus; sugarcane weevils: Sphenophorus levis & Metamasius hemipterus; termites for soybeans, sugarcane, pasture, others: Heterotermes tenuis; Heterotermes longiceps; Cornitermes cumulans; Procornitermes triacifer ; Neocapritermes opacus; Neocapritermes parvus; corn root worms for corn and potatoes:
Diabrotica spp., seed Maggot: Delia platura; soil stinkbugs: Scaptocoris castanea; wireworms: Agriotes spp; Athous spp Hipnodes bicolor; Ctenicera destructor; Limonius canu; Limonius californicus; rice water weevil: Lissorhoptrus oryzophilus; Red Legged earth mites: Halotydeus destructor.
The invention therefore provides a method of combating and/or controlling an animal pest, e.g. an invertebrate animal pest, which comprises applying to the pest, to a locus of the pest, or to a plant susceptible to attack by the pest a pesticidally effective amount of a compound of formula (IA) . In particular, the invention provides a method of combating and/or controlling insects, acarines, nematodes or molluscs which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (IA) , or a composition containing a compound of formula (IA) , to a pest, a locus of pest, preferably a plant, or to a plant susceptible to attack by a pest, The compounds of formula (IA) are preferably used against insects, acarines or nematodes.
The term "plant" as used herein includes seedlings, bushes and trees. Crops are to be understood as also including those crops which have been rendered tolerant to herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO- and HPPD-inhibitors) by conventional methods of breeding or by genetic engineering. An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer rape (canola). Examples of crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate- resistant maize varieties commercially available under the trade names RoundupReady® and
LibertyLink®.
The compounds of the invention may be applied to plant parts. Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. The plant parts also include harvested material, and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds. Treatment according to the invention of the plants and plant parts with the active compounds is carried out directly or by allowing the compounds to act on their surroundings, habitat or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on, injecting and, in the case of propagation material, in particular in the case of seed, also by applying one or more coats.
Compounds of formula (IA) may be used on transgenic plants (including cultivars) obtained by genetic engineering methods and/or by conventional methods. These are understood as meaning plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive "synergistic") effects.
Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected.
The preferred transgenic plants or plant cultivars which are to be treated according to the invention include all plants which, by virtue of the genetic modification, received genetic material which imparts particularly advantageous, useful traits to these plants. Examples of such traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products.
Further and particularly emphasized examples of such traits are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active compounds.
Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soybean, potatoes, sugar beet, tomatoes, peas and other vegetable varieties, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes).
Compounds of formula (IA) may be used on transgenic plants that are capable of producing one or more pesticidal proteins which confer upon the transgenic plant tolerance or resistance to harmful pests, e.g. insect pests, nematode pests and the like. Such pesticidal proteins include, without limitation, Cry proteins from Bacillus thuringiensis CrylAb, CrylAc, CrylF, Cry2Ab, Cry2Ae, Cry3A, Cry3Bb, or Cry9C; engineered proteins such as modified Cry3A ( US Patent 7,030,295) or CrylA.105; or vegetative insecticidal proteins such as Vipl, Vip2 or Vip3. A full list of Bt Cry proteins and VIPs useful in the invention can be found on the worldwide web at Bacillus thuringiensis Toxin Nomenclature Database maintained by the University of Sussex {see also, Crickmore et al. (1998) Microbiol. Mol. Biol. Rev. 62:807-813). Other pesticidal proteins useful in the invention include proteins of bacteria colonizing nematodes, e.g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome- inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl -transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. Further examples of such pesticidal proteins or transgenic plants capable of synthesizing such proteins are disclosed, e.g., in EP-A 374753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451878, WO 03/18810 and WO 03/52073. The methods for producing such transgenic plants are generally known to the person skilled in the art and some of which are commercially available such as Agrisure®CB (PI) (corn producing CrylAb), Agrisure®RW (P2) (corn producing mCry3A), Agrisure® Viptera (P3) (corn hybrids producing Vip3Aa); Agrisure300GT (P4) (corn hybrids producing CrylAb and mCry3A); YieldGard® (P5) (corn hybrids producing the CrylAb protein), YieldGard® Plus (P6) (corn hybrids producing CrylAb and Cry3Bbl), Genuity® SmartStax® (P7) (corn hybrids with CrylA.105, Cry2Ab2, CrylF, Cry34/35, Cry3Bb) ; Herculex® I (P8) (corn hybrids producing CrylFa) and Herculex®RW (P9) (corn hybrids producing Cry34Abl, Cry35Abl and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]) ; NuCOTN®33B (P10) (cotton cultivars producing CrylAc), Bollgard®I (PI 1) (cotton cultivars producing CrylAc), Bollgard®II (P12) (cotton cultivars producing CrylAc and Cry2Ab2) and VIPCOT® (P13) (cotton cultivars producing a Vip3Aa). Soybean Cyst Nematode resistance soybean (SCN® - Syngenta (PI 4)) and soybean with Aphid resistant trait (AMT® (PI 5)) are also of interest.
Further examples of such transgenic crops are:
1. Btll Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10 (PI 6). Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer {Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated CrylA(b) toxin. Btl 1 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.
2. Btl 76 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10 (PI 7). Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer {Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a CrylA(b) toxin. Btl 76 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.
3. MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10 (PI 8). Maize which has been rendered insect-resistant by transgenic expression of a modified CrylllA toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-D-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.
4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-l 150 Brussels, Belgium, registration number C/DE/02/9 (P19). MON 863 expresses a CrylllB(bl) toxin and has resistance to certain Coleoptera insects.
5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-l 150 Brussels, Belgium, registration number C/ES/96/02. (P20) 6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-l 160 Brussels, Belgium, registration number C/NL/00/10. (P21) Genetically modified maize for the expression of the protein Cry IF for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium.
7. NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren,
B-l 150 Brussels, Belgium, registration number C/GB/02/M3/03 (P22). Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 χ MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylA(b) toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
Further examples of transgenic plants, and of very high interest, are those carrying traits conferring resistance to 2.4D (e.g. Enlist®) (e.g. WO 2011066384) (P23), glyphosate (e.g. Roundup Ready® (P24), Roundup Ready 2 Yield® (P25)), sulfonylurea (e.g. STS®) (P26), glufosinate (e.g.
Liberty Link® (P27), Ignite® (P28)), Dicamba (P29) (Monsanto), HPPD tolerance (P30) (e.g.
isoxaflutole herbicide) (Bayer CropScience, Syngenta). Double or triple stacks of any of the traits described here are also of interest, including glyphosate and sulfonyl-urea tolerance ((e.g. Optimum GAT®) (P31), plants stacked with STS® and Roundup Ready® (P32) or plants stacked with STS® and Roundup Ready 2 Yield® (P33)), dicamba and glyphosate tolerance (P34) (Monsanto). Of particular interest are soybean plants carrying trains conferring resistance to 2.4D (e.g. Enlist®), glyphosate (e.g. Roundup Ready®, Roundup Ready 2 Yield®), sulfonylurea (e.g. STS®), glufosinate (e.g. Liberty Link®, Ignite®), Dicamba (Monsanto) HPPD tolerance (e.g. isoxaflutole herbicide) (Bayer CropScience, Syngenta). Double or triple stack in soybean plants of any of the traits described here are also of interest, including glyphosate and sulfonyl-urea tolerance (e.g. Optimum GAT®, plants stacked with STS® and Roundup Ready® or Roundup Ready 2 Yield®), dicamba and glyphosate tolerance (Monsanto).
Transgenic crops of insect-resistant plants are also described in BATS (Zentrum fur Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report 2003, (http://bats.ch).
Examples of cotton transgenic events include MON 531 / 757 / 1076 (Bollgard I ® - Monsanto), MON1445 (Roundup ready cotton ®- Monsanto), MON531 x MON1445 (Bollgard I + RR ®- Monsanto), MON15985 (Genuity Bollgard II cotton ®- Monsanto), MON88913 (Genuity RR FLEX cotton ®- Monsanto), MON15985 x MON1445 (Genuity Bollgard II + RR FELX cotton ®- Monsanto), MON15983 x MON88913 (Genuity Bollgard II + RR FLEX cotton ® - Monsanto), MON15985 (FibreMax Bollgard II Cotton ® - Monsanto), LL25 (FibreMax LL cotton ® - BCS Stoneville), GHB614 (FibreMax GlyTol cotton ®- BCS Stoneville), LL25 x MON15985 (FibreMax LL Bollgard II cotton ® - BCS Stoneville / Monsanto), GHB614 x LL25 (FibreMax LL GlyTol cotton ® - BCS Stoneville), GHB614 x LL25 x MON15985 (FibreMax RR GlyTol Bollgard II cotton ® - BCS Stoneville), MON88913 x MON15985 (FibreMax LL GlyTol Bollgard II cotton ® - Monsanto), MON88913 (FibreMax RR Flex cotton ® - Monsanto), GHB119 + T304-40 (Twinlink ® - BCS Stoneville), GHB119 + T304-40 x LL25 x GHB614 (Twinlink LL GT ® - BCS Stoneville), 3006-210-23 x 281-24-236 (PhytoGen
Widestrike Insect Protection ® - Dow), 3006-210-23 x 281-24-236 x MON88913 (PhytoGen Widestrike Insect Protection + RR FLEX - ® Dow / Monsanto), 3006-210-23 x 281 -24-236 x MON1445 ((PhytoGen Widestrike Insect Protection + RR ® - Dow / Monsanto), MON1445 (PhytoGen Roundup Ready ® - Monsanto), MON88913 (PhytoGen Roundup Ready FLEX ® - Monsanto), COT102 x COT67B (Vipcot ® - Syngenta), COT102 x COT67B x MON88913 (Vipcot RR FLEX ® - Syngenta / Monsanto), 281-24-236 (Dow), 3006-210-23 (Dow), COT102 (Syngenta), COT67B (Syngenta), T304-40 (BCS Stoneville).
Examples of Soy transgenic events include MON87701 x MON89788 (Genuity Roundup ready 2 Yield soybeans® - Monsanto), MON89788 (Roundup Ready2Yield®, RR2Y® - Monsanto), MON87708 (Monsanto), 40-3-2 (Roundup Ready®, RRl® - Monsanto),
MON87701 (Monsanto), DAS-68416 (Enlist Weed Control System® - Dow), DP356043 (Optimum GAT® - Pioneer), A5547-127 (LibertyLink soybean® - Bayercropscience), A2704- 12 (Bayercropscience), GU262 (Bayercropscience), W62 W98 (Bayercropscience), CRV127 (Cultivance® - BASF / EMBRAPA).
Examples of Maize transgenic events include T25 (LibertyLink®, LL® - Bayerscropscience), DHT-1 (Dow), TC1507 (Herculex I® - Dow), DAS59122-7 (Herculex RW® - Dow), TC1507 + DAS59122-7 - Herculex Xtra® - Dow), TC1507 x DAS-59122-7 x NK603 (Herculex Xtra + RR® - Dow), TC1507 x DAS-59122- x MON88017 x MON89034 (Genuity Smartstax corn®, Genuity Smartstax RIB complete® - Monsanto / Dow), MON89034 x NK603 (Genuity VT double PRO® - Monsanto), MON89034 + MON88017 (Genuity VT Triple PRO® - Monsanto), NK603 (Roundup Ready 2®, RR2® - Monsanto), MON810 (YieldGard BT® , Yieldgard cornborer® - Monsanto), MON810 x NK603 (YieldGard cornborer RR Corn 2® - Monasnto), MON810 x MON863 (YieldGard Plus® - Monsanto), MON863 x MON810 x NK603 (YieldGard Plus + RR Corn2® / YieldGard RR Maize® - Monsanto), MON863 x NK603 (YieldGard Rotworm + RR Corn 2® - Monsanto), MON863 (YieldBard RW® - Monsanto), MON89034 (YieldGard RW® - Monsanto), MON88017 (YieldGard VT RW® - Monsanto), MON810 + MON88017 (YieldGard VT Triple® - Monsanto), MON88017 + MON89034 (YieldGard VT Triple Pro® - Monsanto), Btl 1 + MIR604 + GA21 (Agrisure 3000® - Syngenta), Btl 1 + TCI 507 + MIR604 + 5307 + GA21 (Syngenta), Btl 1 + TCI 507 + MIR604 + DAS59122 + GA21 (Agrisure 3122® - Syngenta), BT11 (Agrisure CB® - Syngenta), GA21 - (Agrisure GT® - Syngenta), MIR604 (Agrisure RW® - Syngenta), Btl 1 + MIR162 (Agrisure TL VIP® - Syngenta), BT11 + MIR162 + GA21 (Agrisure Viptra 3110® - Syngenta), BT11 + MIR162 + MIR604 (Agrisure TM 3100® - Syngenta), Event3272 + BT11 + MIR604 + GA21 (Syngenta), BT11 + MIR1692 + MIR604 + GA21 (Agrisure Viptera 3111® - Syngenta), BT11 + MIR 162 + TC1507 + GA21 (Agrisure Viptera 3220® - Syngenta), BT11 + MIR162 + TCI 507 + MIR604 + 5307 + GA21 (Agrisure Viptera 3222® - Syngenta), MIR162 (Syngenta), BT11 + GA21 + MIR162 + MIR604 + 5307 (Syngenta), 5307 (Syngenta).
In order to apply a compound of formula (IA) as an insecticide, acaricide, nematicide or molluscicide to a pest, a locus of pest, or to a plant susceptible to attack by a pest, a compound of formula (IA) is usually formulated into a composition which includes, in addition to the compound of formula (IA) , a suitable inert diluent or carrier and, optionally, a surface active agent (SFA). SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting). It is preferred that all compositions (both solid and liquid formulations) comprise, by weight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%>, of a compound of formula (IA) . The composition is generally used for the control of pests such that a compound of formula (IA) is applied at a rate of from O.lg to 10kg per hectare, preferably from lg to 6kg per hectare, more preferably from lg to 1kg per hectare.
When used in a seed dressing, a compound of formula (IA) is generally used at a rate of 0.000 lg to lOg (for example O.OOlg or 0.05g), preferably 0.005g to lOg, more preferably 0.005g to 4g, per kilogram of seed.
In another aspect the present invention provides a composition comprising a pesticidally effective amount of a compound of formula (IA) , in particular an insecticidal, acaricidal, nematicidal or molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (IA) and a suitable carrier or diluent therefor. The composition is preferably an insecticidal, acaricidal, nematicidal or molluscicidal composition.
The compositions can be chosen from a number of formulation types, including dustable powders
(DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro-emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations. The formulation type chosen in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of formula (IA) .
Dustable powders (DP) may be prepared by mixing a compound of formula (IA) with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder. Soluble powders (SP) may be prepared by mixing a compound of formula (IA) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulfate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water
dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG).
Wettable powders (WP) may be prepared by mixing a compound of formula (IA) with one or more solid diluents or carriers, one or more wetting agents and, preferably, one or more dispersing agents and, optionally, one or more suspending agents to facilitate the dispersion in liquids. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water dispersible granules (WG).
Granules (GR) may be formed either by granulating a mixture of a compound of formula (IA) and one or more powdered solid diluents or carriers, or from pre-formed blank granules by absorbing a compound of formula (IA) (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of formula (IA) (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulfates or phosphates) and drying if necessary. Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).
Dispersible Concentrates (DC) may be prepared by dissolving a compound of formula (IA) in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surface active agent (for example to improve water dilution or prevent crystallization in a spray tank).
Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may be prepared by dissolving a compound of formula (IA) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents). Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids (such as Cg-Cio fatty acid dimethylamide) and chlorinated hydrocarbons. An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment. Preparation of an EW involves obtaining a compound of formula (IA) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifiying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion. Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water.
Microemulsions (ME) may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation. A compound of formula (IA) is present initially in either the water or the solvent/SFA blend. Suitable solvents for use in MEs include those hereinbefore described for use in ECs or in EWs. An ME may be either an oil-in-water or a water-in-oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation. An ME is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil-in-water emulsion.
Suspension concentrates (SC) may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of formula (IA) . SCs may be prepared by ball or bead milling the solid compound of formula (IA) in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound. One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle. Alternatively, a compound of formula (IA) may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.
Aerosol formulations comprise a compound of formula (IA) and a suitable propellant (for example « -butane). A compound of formula (IA) may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non-pressurized, hand-actuated spray pumps.
A compound of formula (IA) may be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in an enclosed space, a smoke containing the compound.
Capsule suspensions (CS) may be prepared in a manner similar to the preparation of EW formulations but with an additional polymerization stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of formula (IA) and, optionally, a carrier or diluent therefor. The polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure. The compositions may provide for controlled release of the compound of formula (IA) and they may be used for seed treatment. A compound of formula (IA) may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.
A composition may include one or more additives to improve the biological performance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of formula (IA) ). Such additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of formula (IA). A compound of formula (IA) may also be formulated for use as a seed treatment, for example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry treatment (WS), or as a liquid composition, including a flowable concentrate (FS), a solution (LS) or a capsule suspension (CS). The preparations of DS, SS, WS, FS and LS compositions are very similar to those of, respectively, DP, SP, WP, SC and DC compositions described above. Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-forming barrier).
Wetting agents, dispersing agents and emulsifying agents may be surface SFAs of the cationic, anionic, amphoteric or non-ionic type.
Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts.
Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulfuric acid (for example sodium lauryl sulfate), salts of sulfonated aromatic compounds (for example sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalene sulfonate and mixtures of sodium di-z' opropyl- and tri-wopropyl-naphthalene sulfonates), ether sulfates, alcohol ether sulfates (for example sodium laureth-3 -sulfate), ether carboxylates (for example sodium laureth-3- carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid; additionally these products may be ethoxylated), sulfosuccinamates, paraffin or olefine sulfonates, taurates and lignosulfonates.
Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.
Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide);
alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.
Suitable suspending agents include hydrophilic colloids (such as polysaccharides,
polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).
A compound of formula (IA) may be applied by any of the known means of applying pesticidal compounds. For example, it may be applied, formulated or unformulated, to the pests or to a locus of the pests (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapor or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water- soluble bag) in soil or an aqueous environment.
A compound of formula (IA) may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.
Compositions for use as aqueous preparations (aqueous solutions or dispersions) are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being added to water before use. These concentrates, which may include DCs, SCs, ECs, EWs, MEs, SGs, SPs, WPs, WGs and CSs, are often required to withstand storage for prolonged periods and, after such storage, to be capable of addition to water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment. Such aqueous preparations may contain varying amounts of a compound of formula (IA) (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.
A compound of formula (IA) may be used in mixtures with fertilizers (for example nitrogen-, potassium- or phosphorus-containing fertilizers). Suitable formulation types include granules of fertilizer. The mixtures preferably contain up to 25% by weight of the compound of formula (IA) .
The invention therefore also provides a fertilizer composition comprising a fertilizer and a compound of formula (IA) .
The compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.
The compound of formula (IA) may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as a pesticide, e.g. a insecticide, fungicide or herbicide, or a synergist or plant growth regulator where appropriate. An additional active ingredient may provide a composition having a broader spectrum of activity or increased persistence at a locus; synergize the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of formula (IA) ; or help to overcome or prevent the development of resistance to individual components. The particular additional active ingredient will depend upon the intended utility of the composition. Examples of suitable pesticides include the following:
a) Pyrethroids, such as permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin (in particular lambda-cyhalothrin and gamma cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin, S-bioallethrin, fenfluthrin, prallethrin, acrinathirin, etofenprox or 5-benzyl-3-furylmethyl-(E)-(lR,3S)-2,2-dimethyl- 3-(2-oxothiolan-3-ylidenemethyl)cyclopropane carboxylate;
b) Organophosphates, such as profenofos, sulprofos, acephate, methyl parathion, azinphos-methyl, demeton-s -methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl, pirimiphos-ethyl, fenitrothion, fosthiazate or diazinon; c) Carbamates (including aryl carbamates), such as pirimicarb, triazamate, cloethocarb, carbofuran, furathiocarb, ethiofencarb, aldicarb, thiofurox, carbosulfan, bendiocarb, fenobucarb, propoxur, methomyl or oxamyl;
d) Benzoyl ureas, such as diflubenzuron, triflumuron, hexaflumuron, flufenoxuron, diafenthiuron, lufeneron, novaluron, noviflumuron or chlorfluazuron;
e) Organic tin compounds, such as cyhexatin, fenbutatin oxide or azocyclotin;
f) Pyrazoles, such as tebufenpyrad, tolfenpyrad, ethiprole, pyriprole, fipronil, and fenpyroximate;
g) Macrolides, such as avermectins or milbemycins, for example abamectin, emamectin benzoate, ivermectin, milbemycin, spinosad, azadirachtin, milbemectin, lepimectin or spinetoram;
h) Hormones or pheromones;
i) Organochlorine compounds, such as endosulfan (in particular alpha-endosulfan), benzene hexachloride,
DDT, chlordane or dieldrin;
j) Amidines, such as chlordimeform or amitraz;
k) Fumigant agents, such as chloropicrin, dichloropropane, methyl bromide or metam;
1) Neonicotinoid compounds, such as imidacloprid, thiacloprid, acetamiprid, nitenpyram, dinotefuran, thiamethoxam, clothianidin, or nithiazine;
m) Diacylhydrazines, such as tebufenozide, chromafenozide or methoxyfenozide;
n) Diphenyl ethers, such as diofenolan or pyriproxifen;
o) Pyrazolines such as Indoxacarb or metaflumizone;
p) Ketoenols, such as Spirotetramat, spirodiclofen or spiromesifen;
q) Diamides, such as flubendiamide, chlorantraniliprole (Rynaxypyr®) or cyantraniliprole;
r) Essential oils such as Bugoil® - (Plantlmpact); or
s) a comopund selected from buprofezine, flonicamid, acequinocyl, bifenazate, cyenopyrafen, cyflumetofen, etoxazole, flometoquin, fluacrypyrim, fluensulfone, flufenerim, flupyradifuone, harpin, iodomethane, dodecadienol, pyridaben, pyridalyl, pyrimidifen, flupyradifurone, 4-[(6-Chloro-pyridin-3- ylmethyl)-(2,2-difluoro-ethyl)-amino]-5H-furan-2-one (DE 102006015467), CAS: 915972-17-7
(WO 2006129714; WO2011/147953; WO2011/147952), CAS: 26914-55-8 (WO 2007020986), chlorfenapyr, pymetrozine, sulfoxaflor and pyrifluqinazon.
In addition to the major chemical classes of pesticide listed above, other pesticides having particular targets may be employed in the composition, if appropriate for the intended utility of the composition. For instance, selective insecticides for particular crops, for example stemborer specific insecticides (such as cartap) or hopper specific insecticides (such as buprofezin) for use in rice may be employed. Alternatively insecticides or acaricides specific for particular insect species/stages may also be included in the compositions (for example acaricidal ovo-larvicides, such as clofentezine, flubenzimine, hexythiazox or tetradifon; acaricidal motilicides, such as dicofol or propargite; acaricides, such as bromopropylate or chlorobenzilate; or growth regulators, such as hydramethylnon, cyromazine, methoprene, chlorfluazuron or diflubenzuron). Examples of fungicidal compounds which may be included in the composition of the invention are (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide (SSF-129), 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole-l -sulfonamide,
-[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]-y-butyrolactone, 4-chloro-2-cyano-N,N-dimethyl-5-/ tolylimidazole-1 -sulfonamide (IKF-916, cyamidazosulfamid), 3-5-dichloro-N-(3-chloro-l-ethyl-l -methyl-
2- oxopropyl)-4-methylbenzamide (RH-7281 , zoxamide), N-allyl-4,5,-dimethyl-2-trimethylsilylthiophene-
3- carboxamide (MON65500), N-(l -cyano-1 ,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)propionamide (AC382042), N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide, acibenzolar (CGA245704) (e.g. acibenzolar-S-methyl), alanycarb, aldimorph, anilazine, azaconazole, azoxystrobin, benalaxyl, benomyl, benthiavalicarb, biloxazol, bitertanol, bixafen, blasticidin S, boscalid, bromuconazole, bupirimate, captafol, captan, carbendazim, carbendazim chlorhydrate, carboxin, carpropamid, carvone, CGA41396, CGA41397, chinomethionate, chlorothalonil, chlorozolinate, clozylacon, copper containing compounds such as copper oxychloride, copper oxyquinolate, copper sulfate, copper tallate and Bordeaux mixture, cyclufenamid, cymoxanil, cyproconazole, cyprodinil, debacarb, di-2-pyridyl disulfide 1,1 '-dioxide, dichlofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, difenzoquat, diflumetorim,
OjO-di-wo-propyl-S-benzyl thiophosphate, dimefluazole, dimetconazole, dimethomorph, dimethirimol, diniconazole, dinocap, dithianon, dodecyl dimethyl ammonium chloride, dodemorph, dodine, doguadine, edifenphos, epoxiconazole, ethirimol, ethyl-(Z)-N-benzyl-N-([methyl(methyl-thioethylideneamino- oxycarbonyl)amino]thio)- -alaninate, etridiazole, famoxadone, fenamidone (RPA407213), fenarimol, fenbuconazole, fenfuram, fenhexamid (KBR2738), fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, fluopyram,
fluoxastrobin, fluoroimide, fluquinconazole, flusilazole, flutolanil, flutriafol, fluxapyroxad, folpet, fuberidazole, furalaxyl, furametpyr, guazatine, hexaconazole, hydroxyisoxazole, hymexazole, imazalil, imibenconazole, iminoctadine, iminoctadine triacetate, ipconazole, iprobenfos, iprodione, iprovalicarb (SZX0722), isopropanyl butyl carbamate, isoprothiolane, isopyrazam, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, mandipropamid, maneb, mefenoxam, metalaxyl, mepanipyrim, mepronil, metalaxyl, metconazole, metiram, metiram-zinc, metominostrobin, myclobutanil, neoasozin, nickel dimethyldithiocarbamate, nitrothal-wopropyl, nuarimol, ofurace, organomercury compounds, oxadixyl, oxasulfuron, oxolinic acid, oxpoconazole, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, penthiopyrad, phenazin oxide, phosetyl-Al, phosphorus acids, phthalide, picoxystrobin (ZA1963), polyoxinD, polyram, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, propionic acid, prothioconazole, pyrazophos, pyrifenox, pyrimethanil, pyraclostrobin, pyroquilon, pyroxyfur, pyrrolnitrin, quaternary ammonium compounds, quinomethionate, quinoxyfen, quintozene, sedaxane, sipconazole (F-155), sodium pentachlorophenate, spiroxamine, streptomycin, sulfur, tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, thifluzamid, 2-(thiocyanomethylthio)benzothiazole, thiophanate -methyl, thiram, timibenconazole, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, tricyclazole, tridemorph, trifloxystrobin (CGA279202), triforine, triflumizole, triticonazole, validamycin A, vapam, vinclozolin, zineb and ziram, N- [9 -(dichloromethylene) -1,2,3,4 -tetrahydro- 1 ,4-methanonaphthalen-5 -yl] -3 -(difluoromethyl) - 1 -methyl- 1 H-pyrazole-4-carboxamide [1072957-71 -1], 1 -methyl-3 -difluoromethyl- 1 H-pyrazole-4-carboxylic acid (2-dichloromethylene-3-ethyl-l-methyl-indan-4-yl)-amide, and 1 -methyl-3 -difluoromethyl-4H-pyrazole- 4-carboxylic acid [2-(2,4-dichloro-phenyl)-2-methoxy-l -methyl-ethyl] -amide.
In addition, biological agents may be included in the composition of the invention e.g. Baciullus species such as Bacillus firmus, Bacillus cereus, Bacillus subtilis, and Pasteuria species such as Pasteuria penetrans and Pasteuria nishizawae. A suitable Bacillus firmus strain is strain CNCM 1-1582 which is commercially available as BioNem™. A suitable Bacillus cereus strain is strain CNCM 1-1562. Of both Bacillus strains more details can be found in US 6,406,690. Other biological organisms that may be included in the compositions of the invention are bacteria such as Streptomyces spp. such as S.
avermitilis, and fungi such as Pochonia spp. such as P. chlamydosporia. Also of interest are Metarhizium spp. such as M. anisopliae; Pochonia spp. such as P. chlamydosporia.
The compounds of formula (IA) may be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.
Examples of suitable synergists for use in the compositions include piperonyl butoxide, sesamex, safroxan and dodecyl imidazole.
Suitable herbicides and plant-growth regulators for inclusion in the compositions will depend upon the intended target and the effect required.
An example of a rice selective herbicide which may be included is propanil. An example of a plant growth regulator for use in cotton is PIX™.
Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type. In these circumstances other formulation types may be prepared. For example, where one active ingredient is a water insoluble solid and the other a water insoluble liquid, it may nevertheless be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that of an SC) but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resultant composition is a suspoemulsion (SE) formulation.
The compounds of the invention are also useful in the field of animal health, e.g. they may be used against parasitic invertebrate pests, more preferably against parasitic invertebrate pests in or on an animal. Examples of pests include nematodes, trematodes, cestodes, flies, mites, tricks, lice, fleas, true bugs and maggots. The animal may be a non-human animal, e.g. an animal associated with agriculture, e.g. a cow, a pig, a sheep, a goat, a horse, or a donkey, or a companion animal, e.g. a dog or a cat.
In a further aspect the invention provides a compound of the invention for use in a method of therapeutic treatment.
In a further aspect the invention relates to a method of controlling parasitic invertebrate pests in or on an animal comprising administering a pesticidally effective amount of a compound of the invention. The administration may be for example oral administration, parenteral administration or external administration, e.g. to the surface of the animal body. In a further aspect the invention relates to a compound of the invention for controlling parasitic invertebrate pests in or on an animal. In a further aspect the invention relates to use of a compound of the invention in the manufacture of a medicament for controlling parasitic invertebrate pests in or on an animal
In a further aspect, the invention relates to a method of controlling parasitic invertebrate pests comprising administering a pesticidally effective amount of a compound of the invention to the environment in which an animal resides.
In a further aspect the invention relates to a method of protecting an animal from a parasitic invertebrate pest comprising administering to the animal a pesticidally effective amount of a compound of the invention. In a further aspect the invention relates to a compound of the invention for use in protecting an animal from a parasitic invertebrate pest. In a further aspect the invention relates to use of a compound of the invention in the manufacture of a medicament for protecting an animal from a parasitic invertebrate pest.
In a further aspect the invention provides a method of treating an animal suffering from a parasitic invertebrate pest comprising administering to the animal a pesticidally effective amount of a compound of the invention. In a further aspect the invention relates to a compound of the invention for use in treating an animal suffering from a parasitic invertebrate pest. In a further aspect the invention relates to use of a compound of the invention in the manufacture of a medicament for treating an animal suffering from a parasitic invertebrate pest.
In a further aspect, the invention provides a pharmaceutical composition comprising a compound of the invention and a pharmaceutically suitable excipient.
The compounds of the invention may be used alone or in combination with one or more other biologically active ingredients.
In one aspect the invention provides a combination product comprising a pesticidally effective amount of a component A and a pesticidally effective amount of component B wherein component A is a compound of the invention and component B is a compound as described below.
The compounds of the invention may be used in combination with anthelmintic agents. Such anthelmintic agents include, compounds selected from the macrocyclic lactone class of compounds such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives as described in EP- 357460, EP-444964 and EP-594291.
Additional anthelmintic agents include semisynthetic and biosynthetic avermectin/milbemycin derivatives such as those described in US-5015630, WO-9415944 and WO-9522552. Additional anthelmintic agents include the benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole,
mebendazole, oxfendazole, oxibendazole, parbendazole, and other members of the class. Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel. Additional anthelmintic agents include flukicides, such as triclabendazole and clorsulon and the cestocides, such as praziquantel and epsiprantel. - 26δ -
The compounds of the invention may be used in combination with derivatives and analogues of the paraherquamide/marcfortine class of anthelmintic agents, as well as the antiparasitic oxazolines such as those disclosed in US-5478855, US- 4639771 and DE-19520936.
The compounds of the invention may be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO-9615121 and also with anthelmintic active cyclic depsipeptides such as those described in WO-9611945, WO-9319053, WO- 9325543, EP-626375, EP-382173, WO-9419334, EP-382173, and EP-503538.
The compounds of the invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.
The compounds of the invention may be used in combination with terpene alkaloids, for example those described in International Patent Application Publication Numbers W095/19363 or WO04/72086, particularly the compounds disclosed therein.
Other examples of such biologically active compounds that the compounds of the invention may be used in combination with include but are not restricted to the following:
Organophosphates: acephate, azamethiphos, azinphos-ethyl, azinphos- methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, methacriphos, methamidophos, methidathion, methyl- parathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate, phosalone, phosfolan, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos- methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thimeton, triazophos, trichlorfon, vamidothion.
Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717.
Pyrethroids: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E) -
(1 R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta - cyfluthrin, cyfluthrin, a-cypermethrin, beta -cypermethrin, bioallethrin, bioallethrin((S)- cyclopentylisomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin, lambda- cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, Zeta-cypermethrin. Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,
teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.
Other antiparasitics: acequinocyl, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine, diacloden, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, ethofenprox, fenazaquin, flumite, MTI- 800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox, fluproxyfen, halofenprox, hydramethylnon, IKI- 220, kanemite, NC-196, neem guard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pirydaryl, propargite, protrifenbute, pymethrozine, pyridaben, Buprofezine pyrimidifen, NC-1111, R-195,RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosyn, trinactin, verbutin, vertalec, YI-5301.
Fungicides: acibenzolar, aldimorph, ampropylfos, andoprim, azaconazole, azoxystrobin, benalaxyl, benomyl, bialaphos, blasticidin-S, Bordeaux mixture, bromuconazole, bupirimate, carpropamid, captafol, captan, carbendazim, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, copper oxychloride, copper salts, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, cyprofuram, RH-7281, diclocymet, diclobutrazole, diclomezine, dicloran, difenoconazole, RP-407213, dimethomorph, domoxystrobin, diniconazole, diniconazole-M, dodine, edifenphos, epoxiconazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fencaramid, fenpiclonil, fenpropidin,
fenpropimorph, fentin acetate, fluazinam, fludioxonil, flumetover, flumorf/flumorlin, fentin hydroxide, fluoxastrobin, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetyl- aluminium, furalaxyl, furametapyr, hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, krsoxim- methyl, mancozeb, maneb, mefenoxam, mepronil, metalaxyl, metconazole,
metominostrobin/fenominostrobin, metrafenone, myclobutanil, neo-asozin, nicobifen, orysastrobin, oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb, propioconazole, proquinazid, prothioconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetrconazole, thiabendazole, thifluzamide, thiophanate -methyl, thiram, tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole, validamycin, vinclozin.
Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, virus and fungi.
Bactericides: chlortetracycline, oxytetracycline, streptomycin.
Other biological agents: enrofloxacin, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel, triclabendazole. 27Q
When used in combination with other active ingredients, the compounds of the invention are preferably used in combination with the following: imidacloprid, enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, fipronil, ivermectin, omeprazole, tiamulin, benazepril, milbemycin, cyromazine, thiamethoxam, pyriprole, deltamethrin, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, metaflumizone, moxidectin, methoprene (including S-methoprene), clorsulon, pyrantel, amitraz, triclabendazole, avermectin, abamectin, emamectin, eprinomectin, doramectin selamectin, nemadectin, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, tetramisole, levamisole, pyrantel pamoate, oxantel, morantel,
triclabendazole, epsiprantel, fipronil, lufenuron, ecdysone or tebufenozide ; more preferably, enrofloxacin , praziquantel , pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome , florfenicol , buserelin , cefovecin , tulathromycin , ceftiour , selamectin , carprofen , moxidectin, clorsulon, pyrantel, eprinomectin, doramectin, selamectin, nemadectin, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, tetramisole, levamisole, pyrantel pamoate, oxantel, morantel, triclabendazole, epsiprantel, lufenuron or ecdysone; even more preferably enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, moxidectin, clorsulon or pyrantel .
Examples of mixing partner ratios for all mixtures described herein include 100: 1 to 1 :6000, 50: 1 to 1 :50, 20: 1 to 1 :20, even more especially from 10: 1 to 1 : 10, 5:1 to 1 :5, 2: 1 to 1 :2, 4: 1 to 2: 1, 1 : 1, or 5: 1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3: 1, or 3:2, or 2: 1, or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or 1 :600, or 1 :300, or 1 :150, or 1 :35, or 2:35, or 4:35, or 1 :75, or 2:75, or 4:75, or 1 :6000, or 1 :3000, or 1 : 1500, or 1 :350, or 2:350, or 4:350, or 1 :750, or 2:750, or 4:750. Those mixing ratios are understood to include, on the one hand, ratios by weight and also, on other hand, molar ratios.
Of particular note is a combination where the additional active ingredient has a different site of action from the compound of formula I. In certain instances, a combination with at least one other parasitic invertebrate pest control active ingredient having a similar spectrum of control but a different site of action will be particularly advantageous for resistance management. Thus, a combination product of the invention may comprise a pesticidally effective amount of a compound of formula (IA) and pesticidally effective amount of at least one additional parasitic invertebrate pest control active ingredient having a similar spectrum of control but a different site of action.
One skilled in the art recognizes that because in the environment and under physiological conditions salts of chemical compounds are in equilibrium with their corresponding non salt forms, salts share the biological utility of the non salt forms.
Thus a wide variety of salts of compounds of the invention (and active ingredients used in combination with the active ingredients of the invention) may be useful for control of invertebrate pests and animal parasites. Salts include acid-addition salts with inorganic or organic acids such as
hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
The compounds of the invention also include N-oxides. Accordingly, the invention comprises combinations of compounds of the invention including N-oxides and salts thereof and an additional active ingredient including N-oxides and salts thereof.
The compositions for use in animal health may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants). Such formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes. Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone -vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes. Examples of formulation auxiliaries and additives include those listed in McCutcheon 's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.
The compounds of the invention can be applied without other adjuvants, but most often application will be of a formulation comprising one or more active ingredients with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use. One method of application involves spraying a water dispersion or refined oil solution of the combination products. Compositions with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy. Such sprays can be applied from spray containers such as a can, a bottle or other container, either by means of a pump or by releasing it from a pressurized container, e.g., a pressurized aerosol spray can. Such spray compositions can take various forms, for example, sprays, mists, foams, fumes or fog. Such spray compositions thus can further comprise propellants, foaming agents, etc. as the case may be. Of note is a spray composition comprising a pesticidally effective amount of a compound of the invention and a carrier. One
embodiment of such a spray composition comprises a pesticidally effective amount of a compound of the invention and a propellant. Representative propellants include, but are not limited to, methane, ethane, propane, butane, isobutane, butene, pentane, isopentane, neopentane, pentene, hydrofluorocarbons, chlorofluorocarbons, dimethyl ether, and mixtures of the foregoing. Of note is a spray composition (and a method utilizing such a spray composition dispensed from a spray container) used to control at least one parasitic invertebrate pest selected from the group consisting of mosquitoes, black flies, stable flies, deer flies, horse flies, wasps, yellow jackets, hornets, ticks, spiders, ants, gnats, and the like, including individually or in combinations. ^
The controlling of animal parasites includes controlling external parasites that are parasitic to the surface of the body of the host animal (e.g., shoulders, armpits, abdomen, inner part of the thighs) and internal parasites that are parasitic to the inside of the body of the host animal (e.g., stomach, intestine, lung, veins, under the skin, lymphatic tissue). External parasitic or disease transmitting pests include, for example, chiggers, ticks, lice, mosquitoes, flies, mites and fleas. Internal parasites include heartworms, hookworms and helminths. The compounds of the invention may be particularly suitable for combating external parasitic pests. The compounds of the invention may be suitable for systemic and/or non- systemic control of infestation or infection by parasites on animals.
The compounds of the invention may be suitable for combating parasitic invertebrate pests that infest animal subjects including those in the wild, livestock and agricultural working animals. Livestock is the term used to refer (singularly or plurally) to a domesticated animal intentionally reared in an agricultural setting to make produce such as food or fiber, or for its labor; examples of livestock include cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, hens, turkeys, ducks and geese (e.g., raised for meat, milk, butter, eggs, fur, leather, feathers and/or wool), cultured fish, honeybees. By combating parasites, fatalities and performance reduction (in terms of meat, milk, wool, skins, eggs, etc.) are reduced, so that applying the compounds of the invention allows more economic and simple husbandry of animals.
By controlling these pests it is intended to reduce deaths and improve performance (in the case of meat, milk, wool, hides, eggs, honey and the like) and health of the host animal. Also, controlling parasites may help to prevent the transmittance of infectious agents, the term "controlling" referring to the veterinary field, meaning that the active compounds are effective in reducing the incidence of the respective parasite in an animal infected with such parasites to innocuous levels, e.g. the active compound is effective in killing the respective parasite, inhibiting its growth, or inhibiting its proliferation.
The compounds of the invention may be suitable for combating parasitic invertebrate pests that infest companion animals and pets (e.g., dogs, cats, pet birds and aquarium fish), research and experimental animals (e.g., hamsters, guinea pigs, rats and mice), as well as animals raised for/in zoos, wild habitats and/or circuses.
In an embodiment of this invention, the animal is preferably a vertebrate, and more preferably a mammal, avian or fish. In a particular embodiment, the animal subject is a mammal (including great apes, such as humans). Other mammalian subjects include primates (e.g., monkeys), bovine (e.g., cattle or dairy cows), porcine (e.g., hogs or pigs), ovine (e.g., goats or sheep), equine (e.g., horses), canine (e.g., dogs), feline (e.g., house cats), camels, deer, donkeys, buffalos, antelopes, rabbits, and rodents (e.g., guinea pigs, squirrels, rats, mice, gerbils, and hamsters). Avians include Anatidae (swans, ducks and geese),
Columbidae (e.g., doves and pigeons), Phasianidae (e.g., partridges, grouse and turkeys), Thesienidae (e.g., domestic chickens), Psittacines (e.g., parakeets, macaws, and parrots), game birds, and ratites (e.g., ostriches).
Birds treated or protected by the compounds of the invention can be associated with either commercial or noncommercial aviculture. These include Anatidae, such as swans, geese, and ducks, ^
Columbidae, such as doves and domestic pigeons, Phasianidae, such as partridge, grouse and turkeys, Thesienidae, such as domestic chickens, and Psittacines, such as parakeets, macaws and parrots raised for the pet or collector market, among others.
For purposes of the present invention, the term "fish" is understood to include without limitation, the Teleosti grouping of fish, i.e., teleosts. Both the Salmoniformes order (which includes the Salmonidae family) and the Perciformes order (which includes the Centrarchidae family) are contained within the Teleosti grouping. Examples of potential fish recipients include the Salmonidae, Serranidae, Sparidae, Cichlidae, and Centrarchidae, among others.
Other animals are also contemplated to benefit from the inventive methods, including marsupials (such as kangaroos), reptiles (such as farmed turtles), and other economically important domestic animals for which the inventive methods are safe and effective in treating or preventing parasite infection or infestation.
Examples of parasitic invertebrate pests controlled by administering a pesticidally effective amount of the compounds of the invention to an animal to be protected include ectoparasites (arthropods, acarines, etc.) and endoparasites (helminths, e.g., nematodes, trematodes, cestodes, acanthocephalans, etc. and protozoae, such as coccidia).
The disease or group of diseases described generally as helminthiasis is due to infection of an animal host with parasitic worms known as helminths. The term 'helminths' is meant to include nematodes, trematodes, cestodes and acanthocephalans. Helminthiasis is a prevalent and serious economic problem with domesticated animals such as swine, sheep, horses, cattle, goats, dogs, cats and poultry.
Among the helminths, the group of worms described as nematodes causes widespread and at times serious infection in various species of animals.
Nematodes that are contemplated to be treated by the compounds of the invention include, without limitation, the following genera: Acanthocheilonema, Aelurostrongylus , Ancylostoma,
Angiostrongylus , Ascaridia, Ascaris, Brugia, Bunostomum, Capillaria, Chabertia, Cooperia, Crenosoma, Dictyocaulus, Dioctophyme, Dipetalonema, Diphyllobothrium, Dirofilaria, Dracunculus, Enterobius, Filaroides, Haemonchus, Heterakis, Lagochilascaris, Loa, Mansonella, Muellerius, Necator,
Nematodirus , Oesophagostomum, Ostertagia, Oxyuris, Parafilaria, Parascaris, Physaloptera,
Protostrongylus, Setaria, Spirocerca, Stephanofilaria, Strongy ides, Strongylus, Thelazia, Toxascaris, Toxocara, Trichinella, Trichonema, Trichostrongylus, Trichuris, Uncinaria and Wuchereria.
Of the above, the most common genera of nematodes infecting the animals referred to above are Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum,
Oesophagostomum, Chabertia, Trichuris, Strongylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris and Parascaris. Certain of these, such as Nematodirus, Cooperia and Oesophagostomum attack primarily the intestinal tract while others, such as Haemonchus and Ostertagia, are more prevalent in the stomach while others such as Dictyocaulus are found in the lungs. Still other parasites may be located in other tissues such as the heart and blood vessels, subcutaneous and lymphatic tissue and the like.
Trematodes that are contemplated to be treated by the invention and by the inventive methods include, without limitation, the following genera: Alaria, Fasciola, Nanophyetus, Opisthorchis , Paragonimus and Schistosoma.
Cestodes that are contemplated to be treated by the invention and by the inventive methods include, without limitation, the following genera: Diphyllobothrium, Diplydium, Spirometra and Taenia.
The most common genera of parasites of the gastrointestinal tract of humans are
Ancylostoma, Necator, Ascaris, Strongy hides, Trichinella, Capillaria, Trichuris and Enterobius. Other medically important genera of parasites which are found in the blood or other tissues and organs outside the gastrointestinal tract are the filarial worms such as Wuchereria, Brugia, Onchocerca and Loa, as well as Dracunculus and extra intestinal stages of the intestinal worms Strongyloides and Trichinella.
Numerous other helminth genera and species are known to the art, and are also contemplated to be treated by the compounds of the invention. These are enumerated in great detail in Textbook of Veterinary Clinical Parasitology, Volume 1, Helminths, E. J. L. Soulsby, F. A. Davis Co., Philadelphia, Pa.; Helminths, Arthropods and Protozoa, (6thEdition of Monnig's Veterinary Helminthology and Entomology), E. J. L. Soulsby, Williams and Wilkins Co., Baltimore, Md.
The compounds of the invention may be effective against a number of animal ectoparasites (e.g., arthropod ectoparasites of mammals and birds in particular insects such as flies (stinging and licking), parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; or acarids, such as ticks, for examples hard ticks or soft ticks, or mites, such as scab mites, harvest mites, bird mites and the like).
Insect and acarine pests include, e.g., biting insects such as flies and mosquitoes, mites, ticks, lice, fleas, true bugs, parasitic maggots, and the like.
Adult flies include, e.g., the horn fly or Haematobia irritans, the horse fly or Tabanus spp., the stable fly or Stomoxys calcitrans, the black fly or Simulium spp., the deer fly or Chrysops spp., the louse fly or Melophagus ovinus, and the tsetse fly or Glossina spp. Parasitic fly maggots include, e.g., the bot fly (Oestrus ovis and Cuterebra spp.), the blow fly or Phaenicia spp., the screwworm or Cochliomyia hominivorax, the cattle grub or Hypoderma spp., the fleeceworm and the Gastrophilus of horses.
Mosquitoes include, for example, Culex spp., Anopheles spp. and Aedes spp.
Mites include Mesostigmalphatalpha spp. e.g., mesostigmatids such as the chicken mite,
Dermalphanyssus galphallinalphae; itch or scab mites such as Sarcoptidae spp. for example,
Salpharcoptes scalphabiei; mange mites such as Psoroptidae spp. including Chorioptes bovis and Psoroptes ovis; chiggers e.g., Trombiculidae spp. for example the North American chigger,
Trombiculalpha alphalfreddugesi.
Ticks include, e.g., soft-bodied ticks including Argasidae spp. for example Argalphas spp. and
Ornithodoros spp.; hard-bodied ticks including Ixodidae spp., for example Rhipicephalphalus sanguineus, Dermacentor variabilis, Dermacentor andersoni, Amblyomma americanum, Ixodes scapularis and other Rhipicephalus spp. (including the former Boophilus genera). Lice include, e.g., sucking lice, e.g., Menopon spp.
and Bovicola spp.; biting lice, e.g., Haematopinus spp., Linognathus spp. and Solenopotes spp.
Fleas include, e.g., Ctenocephalides spp., such as dog flea {Ctenocephalides canis) and cat flea (Ctenocephalides felis); Xenopsylla spp. such as oriental rat flea (Xenopsylla cheopis); and Pulex spp. such as human flea (Pulex irritans).
True bugs include, e.g., Cimicidae or e.g., the common bed bug (Cimex lectularius); Triatominae spp. including triatomid bugs also known as kissing bugs; for example Rhodnius prolixus and Triatoma spp.
Generally, flies, fleas, lice, mosquitoes, gnats, mites, ticks and helminths cause tremendous losses to the livestock and companion animal sectors. Arthropod parasites also are a nuisance to humans and can vector disease-causing organisms in humans and animals.
Numerous other parasitic invertebrate pests are known to the art, and are also contemplated to be treated by the compounds of the invention. These are enumerated in great detail in Medical and
Veterinary Entomology, D. S. Kettle, John Wiley AND Sons, New York and Toronto; Control of Arthropod Pests of Livestock: A Review of Technology, R. O. Drummand, J. E. George, and S. E. Kunz, CRC Press, Boca Raton, Fla.
The compounds of the invention may also be effective against ectoparasites, e.g. insects such as flies (stinging and licking), parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; or acarids, such as ticks, for examples hard ticks or soft ticks, or mites, such as scab mites, harvest mites, bird mites and the like. These include e.g. flies such as Haematobia (Lyperosia) irritans (horn fly), Simulium spp.
(blackfly), Glossina spp. (tsetse flies), Hydrotaea irritans (head fly), Musca autumnalis (face fly), Musca domestica (house fly), Morellia simplex (sweat fly), Tabanus spp. (horse fly), Hypoderma bovis, Hypoderma lineatum, Lucilia sericata, Lucilia cuprina (green blowfly), Calliphora spp. (blowfly), Protophormia spp., Oestrus ovis (nasal botfly), Culicoides spp. (midges), Hippobosca equine,
Gastrophilus intestinalis, Gastrophilus haemorrhoidalis and Gastrophilus nasalis; lice such as Bovicola (Damalinia) bovis, Bovicola equi, Haematopinus asini, Felicola subrostratus, Heterodoxus spiniger, Lignonathus setosus and Trichodectes canis; keds such as Melophagus ovinus; and mites such as Psoroptes spp., Sarcoptes scabei, Chorioptes bovis, Demodex equi, Cheyletiella spp., Notoedres cati, Trombicula spp. and Otodectes cyanotis (ear mites).
Examples of species of animal health pesets include those from the order of the Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; particular examples are: Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformis, Linognathus pedalis, Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinus eurysternus, Haematopinus suis, Pediculus humanus capitis, Pediculus humanus corporis, Phylloera vastatrix, Phthirus pubis, Solenopotes capillatus; from the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.; particular examples are: Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis, Trichodectes canis, -„ ,
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Felicola subrostratus, Bovicola caprae, Lepikentron ovis, Werneckiella equi; from the order of the Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp.; particular examples are: Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles gambiae, Anopheles maculipennis, Calliphora
erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Fannia canicularis, Sarcophaga carnaria, Stomoxys calcitrans, Tipula paludosa, Lucilia cuprina, Lucilia sericata, Simulium reptans, Phlebotomus papatasi, Phlebotomus longipalpis, Odagmia ornata, Wilhelmia equina, Boophthora erythrocephala, Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Hybomitra ciurea, Chrysops caecutiens, Chrysops relictus, Haematopota pluvialis,
Haematopota italica, Musca autumnalis, Musca domestica, Haematobia irritans irritans, Haematobia irritans exigua, Haematobia stimulans, Hydrotaea irritans, Hydrotaea albipuncta, Chrysomya chloropyga, Chrysomya bezziana, Oestrus ovis, Hypoderma bovis, Hypoderma lineatum, Przhevalskiana silenus, Dermatobia hominis, Melophagus ovinus, Lipoptena capreoli, Lipoptena cervi, Hippobosca variegata, Hippobosca equina, Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophilus pecorum, Braula coeca; from the order of the Siphonapterida, for example Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.; particular examples are: Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of the Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp; from the order of the Blattarida, for example Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp. (e.g. Suppella longipalpa); from the subclass of the Acari (Acarina) and the orders of the Meta- and Mesostigmata, for example Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp Dermacentor spp., Haemophysalis spp., Hyalomma spp., Dermanyssus spp., Rhipicephalus spp. (the original genus of multi host ticks) Ornithonyssus spp., Pneumonyssus spp., RailUetia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; particular examples are: Argas persicus, Argas reflexus, Ornithodorus moubata, Otobius megnini, Rhipicephalus (Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus) calceratus, Hyalomma anatolicum, Hyalomma aegypticum, Hyalomma marginatum, Hyalomma transiens,
Rhipicephalus evertsi, Ixodes ricinus, Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalis otophila, Haemaphysalis leachi, Haemaphysalis longicorni, Dermacentor marginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalomma mauritanicum, Rhipicephalus sanguineus, ^ηη
Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalus turanicus, Rhipicephalus zambeziensis, Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssus sylviarum, Varroa jacobsoni; from the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example Acarapis spp., Cheyletiella spp., Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp. ; particular examples are: Cheyletiella yasguri, Cheyletiella blakei, Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodex caballi, Demodex suis, Neotrombicula autumnalis,
Neotrombicula desaleri, Neoschongastia xerothermobia, Trombicula akamushi, Otodectes cynotis, Notoedres cati, Sarcoptis canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae (S. caprae), Sarcoptes equi, Sarcoptes suis, Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Chorioptes bovis, Psoergates ovis, Pneumonyssoidic mange, Pneumonyssoides caninum, Acarapis woodi; Gasterophilus spp., Stomoxys spp., Trichodectes spp., Rhodnius spp., Ctenocephalides canis, Cimx lecturius,
Ctenocephalides felis, Lucilia cuprina; examples of acari include Ornithodoros spp., Ixodes spp., Boophilus spp..
Treatments of the invention are by conventional means such as by enteral administration in the form of, for example, tablets, capsules, drinks, drenching preparations, granulates, pastes, boli, feed- through procedures, or suppositories; or by parenteral administration, such as, for example, by injection (including intramuscular, subcutaneous, intravenous, intraperitoneal) or implants; or by nasal administration; or by dermal application in the form of, for example, bathing or dipping, spraying, pouring-on and spotting-on, washing, dusting, and with the aid of active -compound-comprising shaped articles such as collars, ear tags, tail tags, limb bands, halters, marking devices and the like.
When compounds of the invention are applied in combination with an additional biologically active ingredient, they may be administered separately e.g. as separate compositions. In this case, the biologically active ingredients may be administered simultaneously or sequentially. Alternatively, the biologically active ingredients may be components of one composition.
The compounds of the invention may be administered in a controlled release form, for example in subcutaneous or orally adminstered slow release formulations.
Typically a parasiticidal composition according to the present invention comprises a compound of the invention, optionally in combination with an additional biologically active ingredient, or N-oxides or salts thereof, with one or more pharmaceutically or veterinarily acceptable carriers comprising excipients and auxiliaries selected with regard to the intended route of administration (e.g., oral or parenteral administration such as injection) and in accordance with standard practice. In addition, a suitable carrier is selected on the basis of compatibility with the one or more active ingredients in the composition, including such considerations as stability relative to pH and moisture content. Therefore of note are compounds of the invention for protecting an animal from an invertebrate parasitic pest - λ /o - comprising a parasitically effective amount of a compound of the invention, optionally in combination with an additional biologically active ingredient and at least one carrier.
For parenteral administration including intravenous, intramuscular and subcutaneous injection, the compounds of the invention can be formulated in suspension, solution or emulsion in oily or aqueous vehicles, and may contain adjuncts such as suspending, stabilizing and/or dispersing agents.
The compounds of the invention may also be formulated for bolus injection or continuous infusion. Pharmaceutical compositions for injection include aqueous solutions of water-soluble forms of active ingredients (e.g., a salt of an active compound), preferably in physiologically compatible buffers containing other excipients or auxiliaries as are known in the art of pharmaceutical formulation.
Additionally, suspensions of the active compounds may be prepared in a lipophilic vehicle. Suitable lipophilic vehicles include fatty oils such as sesame oil, synthetic fatty acid esters such as ethyl oleate and triglycerides, or materials such as liposomes.
Aqueous injection suspensions may contain substances that increase the viscosity of the suspension, such as sodium carboxymethyl cellulose, sorbitol, or dextran. Formulations for injection may be presented in unit dosage form, e.g., in ampoules or in multi-dose containers. Alternatively, the active ingredient may be in powder form for constitution with a suitable vehicle, e.g., sterile, pyrogen-free water, before use.
In addition to the formulations described supra, the compounds of the invention may also be formulated as a depot preparation. Such long acting formulations may be administered by implantation (for example, subcutaneously or intramuscularly) or by intramuscular or subcutaneous injection.
The compounds of the invention may be formulated for this route of administration with suitable polymeric or hydrophobic materials (for instance, in an emulsion with a pharmacologically acceptable oil), with ion exchange resins, or as a sparingly soluble derivative such as, without limitation, a sparingly soluble salt.
For administration by inhalation, the compounds of the invention can be delivered in the form of an aerosol spray using a pressurized pack or a nebulizer and a suitable propellant, e.g., without limitation, dichlorodifluoromethane, trichlorofluoromethane, dichlorotetrafluoroethane or carbon dioxide. In the case of a pressurized aerosol, the dosage unit may be controlled by providing a valve to deliver a metered amount. Capsules and cartridges of, for example, gelatin for use in an inhaler or insufflator may be formulated containing a powder mix of the compound and a suitable powder base such as lactose or starch.
The compounds of the invention may have favourable pharmacokinetic and pharmacodynamic properties providing systemic availability from oral administration and ingestion. Therefore after ingestion by the animal to be protected, parasiticidally effective concentrations of a compound of the invention in the bloodstream may protect the treated animal from blood-sucking pests such as fleas, ticks and lice. Therefore of note is a composition for protecting an animal from an invertebrate parasite pest in a form for oral administration (i.e. comprising, in addition to a parasiticidally effective amount of a ^ compound of the invention, one or more carriers selected from binders and fillers suitable for oral administration and feed concentrate carriers).
For oral administration in the form of solutions (the most readily available form for absorption), emulsions, suspensions, pastes, gels, capsules, tablets, boluses, powders, granules, rumen-retention and feed/water/lick blocks, the compounds of the invention can be formulated with binders/fillers known in the art to be suitable for oral administration compositions, such as sugars and sugar derivatives (e.g., lactose, sucrose, mannitol, sorbitol), starch (e.g., maize starch, wheat starch, rice starch, potato starch), cellulose and derivatives (e.g., methylcellulose, carboxymethylcellulose, ethylhydroxycellulose), protein derivatives (e.g., zein, gelatin), and synthetic polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone). If desired, lubricants (e.g., magnesium stearate), disintegrating agents (e.g., cross-linked
polyvinylpyrrolidinone, agar, alginic acid) and dyes or pigments can be added. Pastes and gels often also contain adhesives (e.g., acacia, alginic acid, bentonite, cellulose, xanthan gum, colloidal magnesium aluminum silicate) to aid in keeping the composition in contact with the oral cavity and not being easily ejected.
In one embodiment a composition of the present invention is formulated into a chewable and/or edible product (e.g., a chewable treat or edible tablet). Such a product would ideally have a taste, texture and/or aroma favored by the animal to be protected so as to facilitate oral administration of the compounds of the invention.
If the parasiticidal compositions are in the form of feed concentrates, the carrier is typically selected from high-performance feed, feed cereals or protein concentrates.
Such feed concentrate -containing compositions can, in addition to the parasiticidal active ingredients, comprise additives promoting animal health or growth, improving quality of meat from animals for slaughter or otherwise useful to animal husbandry.
These additives can include, for example, vitamins, antibiotics, chemotherapeutics, bacteriostats, fungistats, coccidiostats and hormones.
The compound of the invention may also be formulated in rectal compositions such as suppositories or retention enemas, using, e.g., conventional suppository bases such as cocoa butter or other glycerides.
The formulations for the method of this invention may include an antioxidant, such asBHT (butylated hydroxytoluene). The antioxidant is generally present in amounts of at 0.1 - 5 percent (wt/vol). Some of the formulations require a solubilizer, such as oleic acid, to dissolve the active agent, particularly if spinosad is included. Common spreading agents used in these pour-on formulations include isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated C12-C18 fatty alcohols, oleic acid, oleyl ester, ethyl oleate, triglycerides, silicone oils and dipropylene glycol methyl ether. The pour-on formulations for the method of this invention are prepared according to known techniques. Where the pour-on is a solution, the parasiticide/insecticide is mixed with the carrier or vehicle, using heat and stirring if required. Auxiliary or additional ingredients can be added to the mixture of active agent and ΟΛ carrier, or they can be mixed with the active agent prior to the addition of the carrier. Pour-on formulations in the form of emulsions or suspensions are similarly prepared using known techniques.
Other delivery systems for relatively hydrophobic pharmaceutical compounds may be employed. Liposomes and emulsions are well-known examples of delivery vehicles or carriers for hydrophobic drugs. In addition, organic solvents such as dimethylsulfoxide may be used, if needed.
The rate of application required for effective parasitic invertebrate pest control (e.g. "pesticidally effective amount") will depend on such factors as the species of parasitic invertebrate pest to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. One skilled in the art can easily determine the pesticidally effective amount necessary for the desired level of parasitic invertebrate pest control.
In general for veterinary use, the compounds of the invention are administered in a pesticidally effective amount to an animal, particularly a homeothermic animal, to be protected from parasitic invertebrate pests.
A pesticidally effective amount is the amount of active ingredient needed to achieve an observable effect diminishing the occurrence or activity of the target parasitic invertebrate pest. One skilled in the art will appreciate that the pesticidally effective dose can vary for the various compounds and compositions useful for the method of the present invention, the desired pesticidal effect and duration, the target parasitic invertebrate pest species, the animal to be protected, the mode of application and the like, and the amount needed to achieve a particular result can be determined through simple experimentation.
For oral or parenteral administration to animals, a dose of the compositions of the present invention administered at suitable intervals typically ranges from about 0.01 mg/kg to aboutlOO mg/kg, and preferably from about 0.01 mg/kg to about 30 mg/kg of animal body weight.
Suitable intervals for the administration of the compositions of the present invention to animals range from about daily to about yearly. Of note are administration intervals ranging from about weekly to about once every 6 months. Of particular note are monthly adminstration intervals (i.e. administering the compounds to the animal once every month).
formula (IA) The following abbreviations were used throughout this section: s = singlet; bs = broad singlet; d = doublet; dd = double doublet; dt = double triplet; t = triplet, tt = triple triplet, q = quartet, sept = septet; m = multiplet; Me = methyl; Et = ethyl; Pr = propyl; Bu = butyl; RT = retention time; MH+ = molecular cation.
Preparation Examples
The following preparation examples describe synthesis of compounds of formula (IA) and intermediates thereof.
Example PI : 4-(3,5-Dichloro-phenyl)-5,5,5-trifluoro-pent-2-yne-l,4-diol
Figure imgf000283_0001
a stirring solution of magnesium (520 mg) in anhydrous tetrahydrofuran (50 mL) under argon at room temperature, was added ethyl bromide (1.7 mL). After stirring for 2 hours at room temperature, the solution was cooled to 0°C and Trimethyl-prop-2-ynyloxy-silane (3.1 mL) was added. The solution was allowed to warm to room temperature and then after 40 minutes, it was cooled again to 0°C. To this cooled solution, l-(3,5-Dichloro-phenyl)-2,2,2-trifluoro-ethanone (5 g) (Journal of Physical Organic Chemistry (1989), 2(4), 363-6) were added. The solution was stirred at 0°C for 1 hour. The mixture was quenched with saturated ammonium chloride and then extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate and concentrated. The residue was then dissolved in ethyl acetate (60 mL) and the solution was stirred at room temperature under argon. A solution of
tetrabutylammonium fluoride (21 mL of a 1 M solution in tetrahydrofuran) was added. The solution was stirred for one hour then was allowed to stand at room temperature for 21 hours. The mixture was quenched with saturated ammonium chloride and then extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate and concentrated. The residue was purified by
chromatography on silica gel (eluent: heptane / ethyl acetate 1 :0 to 7:3) to give 4-(3,5-Dichloro-phenyl)- 5,5,5-trifluoro-pent-2-yne-l,4-diol (3.798 g) as a colorless oil.
'H-NMR (CDCI3, 400 MHz): 7.61 (m, 2H), 7.43 (t, J=1.83 Hz, 1H), 4.44 (m, 2H), 3.45 (s, 1H) ppm.
Figure imgf000283_0002
To a solution of 4-(3,5-Dichloro-phenyl)-5,5,5-trifluoro-pent-2-yne-l,4-diol (2.5 g) in toluene under argon, was added tetrakis(triphenylphosphine) palladium (190 mg) and tributyltinhydride (2.25 mL). The reaction mixture was stirred for 45 minutes then the solvent was evaporated under vacuo. The residue was then dissolved in anhydrous tetrahydrofuran (50 mL) with triphenylphosphine (2.19 g) and the solution was stirred at 0°C under argon. To this solution was slowly added diethyl azodicarboxylate (1.31 mL). The mixture was stirred at 0°C for 90 minutes then the solvent was evaporated under vacuo.
The residue was partitioned between acetonitrile and heptane and the acetonitrile part was washed twice with heptane. The combined heptane extracts were combined and evaporated to give a residue that was purified by chromatography on silica gel (eluent: heptane) to give Tributyl-[5-(3,5-dichloro-phenyl)-5 rifluoromethyl-2,5-dihydro-furan-3-yl]-stannane (1.587 g) as a colorless oil.
'H-NMR (CDCI3, 400 MHz): 7.43 (m, 2H), 7.34 (d, J=1.83 Hz, 1H), 5.93 (t, J= 2.57 Hz, 1H), 5.02-4.89 (2x dd, J= 2.6 and 13.6 and 1.8 Hz, 2H), 1.52-1.46 (m, 6H), 1.34-1.28 (m, 6H), 1.03-0.99 (t, J=8.1 Hz, 6H), 0.89 (t, J=7.3 Hz, 9H) ppm.
Example P3 : Preparation of 4-bromo-2-methyl -benzoic acid ferf -butyl ester
Figure imgf000284_0001
4-Bromo-2-methyl -benzoic acid (commercially available) (50 g) was suspended in dichloromethane (500 mL). A catalytic amount of NN-dimethylformamide ("DMF") and oxalyl chloride (23 mL) were added to the suspension. The reaction mixture was stirred at ambient temperature for 3 hours. The reaction mixture was concentrated and the residue dissolved in dry tetrahydrofuran (800 mL). The solution was cooled to 2°C and added to a solution of potassium tert-butoxide (39.2 g) in dry tetrahydrofuran (300 mL) dropwise at 5-10°C. The reaction mixture was stirred at ambient temperature for 30 minutes and then poured onto a mixture of ice and water. The mixture was extracted with ethyl acetate. The organic extract was washed with water, dried over sodium sulfate and concentrated to give 4-bromo-2-methyl-benzoic acid tert-butyl ester (65.3 g) as yellow oil.
'H-NMR (CDCI3, 400 MHz): 7.70 (d, 1H), 7.40 (s, 1H), 7.35 (d, 1H), 2.58 (s, 3H), 1.60 (s, 9H).
Example P4: 4-[5-(3.5-Dichloro-phenyl)-5-trifluoromethyl-2.5-dihydro-furan-3-yll-2 -methyl-benzoic acid tert-butyl ester
Figure imgf000284_0002
a solution of
Tributyl-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl]-stannane (1.587 g) in toluene (15 mL) under argon was successively added 4-Bromo-2-methyl-benzoic acid tert-butyl ester (630 mg), lithium chloride (600 mg) and then tetrakis(triphenylphosphine) palladium (110 mg). The reaction was refluxed at 100°C under argon for 3 hours 30 minutes. The reaction was allowed to cool down to room temperature then after 3 hours, more tetrakis(triphenylphosphine) palladium (45 mg) was added. The solution was refluxed for a further lh45 and then the reaction was stopped. The mixture was cooled to room temperature and then the solvent was evaporated in vacuo to give a residue which was purified by - οό - chromatography on silica gel (eluent: heptanes\diethyl ether, from 1 :0 to 9: 1) to give 4-[5-(3,5-Dichloro- phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl]-2-methyl-benzoic acid tert-butyl ester (704 mg) as a white solid. Recrystallisation in heptane/ethyl acetate provided white crystals, m.p= 160-162°C.
¾-NMR (CDCI3, 400 MHz): 7.83 (d, J= 8.4 Hz, IH), 7.50 (m, 2H), 7.38 (t, J= 1.4 Hz, IH), 7.22 (m, 2H), 6.39 (m, IH), 5.32 (dd, J= 2.2 and 12.5 Hz, IH), 5.20 (m, IH), 2.59 (s, 3H), 1.61 (s, 9H) ppm.
Example P5: 4-[5-(3.5-Dichloro-phenyl)-5 rifluoromethyl-2.5-dihydro-furan-3-yll-2-methyl-benzoic
Figure imgf000285_0001
To a solution of 4-[5-(3,5-Dichloro-phenyl)-5 rifluoromethyl-2,5-dihydro-furan-3-yl]-2-methyl-benzoic acid tert-butyl ester (322 mg) in dichloromethane (8 mL ) was added trifluoroacetic acid (0.5 niL). The reaction mixture was stirred at room temperature for 3h30 then the solution was concentrated under vacuo to give 4-[5-(3,5-Dichloro-phenyl)-5 rifluoromethyl-2,5-dihydro-furan-3-yl]-2-methyl-benzoic acid (200 mg) as a white foam.
¾-NMR (CDCI3, 400 MHz): 8.07 (d, J= 8.8 Hz, IH), 7.49 (m, 2H), 7.39 (t, J= 1.4 Hz, IH), 7.3-7.26 (m, 2H), 6.46 (m, IH), 5.34 (dd, J= 2.2 and 12.5 Hz, IH), 5.22 (m, IH), 2.67 (s, 3H) ppm.
Example P6 (compound Al from Table A): 4-[5-(3.5-Dichloro-phenyl)-5-trifluoromethyl-2.5-dihydro- furan-3 -yl] -2-methyl-N-[(2.2.2-trifluoro-ethylcarbamoyl)-ethyll -benzamide
Figure imgf000285_0002
a stirred solution of 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl]-2-methyl- benzoic acid (50 mg) in dichloromethane (2 mL) was added triethylamine (0.04 mL) at ambient temperature. The solution was then stirred for 5 min under argon and the trifluoroacetate salt of 2-amino- N-(2,2,2-trifluoro-ethyl)-acetamide (39 mg, prepared according to JP2009173621) was added. To this solution, 1 -hydroxyazabenzotriazole (18 mg) then N,N'-Dicyclohexylcarbodiimide (27 mg) were added. The solution was stirred for 80 minutes then was allowed to stand at ambient temperature for 3 days. The solution was concentrated under vacuo and then the crude residue was first purified by chromatography on silica gel (eluent: heptane/ethyl acetate, from 1 :0 to 6:4). The residue was further recrystallysed and - o4 - repurified by preparative HPLC to give 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan- 3-yl]-2-methyl-N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide (30 mg) as a white solid.
¾-NMR (CDCI3, 400 MHz): 7.49 (m, 2H), 7.44 (d, 1H, J= 7.7 Hz), 7.38 (m, 1H), 7.26-7.22 (m, 2H), 7.00 (m, 1H), 6.69 (m, 1H), 6.39 (m, 1H), 5.32 (dd, J= 2.2 and 12.5 Hz, 1H), 5.19 (m, 1H), 4.22 (d, J=5.14 Hz, 2H), 4.00-3.92 (m, 2H), 2.47 (s, 3H) ppm.
Similarly, using the trifluoroacetate salt of (S)-4-Amino-2-ethyl-isoxazolidin-3-one and l-(3- Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1 -hydroxyazabenzotriazole as coupling agents, 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl]-N
-((S)-2-ethyl-3-oxo-isoxazolidin-4-yl)-2-methyl-benzamide (compound A16 from Table A): could be prepared. 'H-NMR (CDCI3, 400 MHz): 7.49-7.48 (m, 3H), 7.38 (m, 1H), 7.27-7.21 (m, 2H), 6.43 (s, 1H), 6.39 (s, 1H), 5.32 (dd, J= 2.2 and 12.4 Hz, 1H), 5.18 (bd, 1H, J= 12.2 Hz), 5.00 (t, 1H, J= 8.07 Hz), 4.88- 4.82 (m, 1H), 4.08-4.03 (m, 1H), 3.75-3.62 (m, 2H), 2.49 (s, 3H), 1.27 (m, 3H) ppm. 19F-NMR (CDC13, 376 MHz): -78.13 ppm.
Similarly, using 2-Chloro-6-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl] -nicotinic acid as a starting material and l-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1- hydroxyazabenzotriazole as coupling agents, 2-Chloro-6-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-2,5- dihydro-furan-3-yl]-N-[(2,2,2-trifluoro- ethylcarbamoyl) -methyl] -nicotinamide (compound Fl from Table F) could be prepared. ¾-NMR (CDC13, 400 MHz): 8.16 (d, 1H, J= 7.70 Hz), 7.49 (m, 2H), 7.46-7.43 (m, 2H), 7.39 (t, 1H, J= 1.83 Hz), 6.81 (m, 1H), 6.69 (m, 1H), 5.40 (dd, J= 2.2 and 13.2 Hz, 1H), 5.27 (bd, 1H, J= 13.2 Hz), 4.26 (d, 2H, J= 5.14 Hz), 4.02-3.94 (m, 2H) ppm. "F-NMR (CDCI3, 376 MHz): -77.88 and -72.44 ppm. Similarly, using 2-Chloro-6-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl] -nicotinic acid as a starting material, l-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1- hydroxyazabenzotriazole as coupling agents, and the trifluoroacetate salt of l,l -Dioxo-llambda*6*- thietan-3-ylamine, 2-Chloro-6-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl]-N-(l,l- dioxo-llambda*6*-thietan-3-yl)-nicotinamide (compound F2 from Table F) could be prepared. 'H-NMR (CDCI3, 400 MHz): 8.20 (d, 1H, J= 8.07 Hz), 7.50-7.46 (m, 3H), 7.40-7.37 (m, 2H), 6.82 (m, 1H), 5.40 (dd, J= 2.2 and 13.2 Hz, 1H), 5.28 (bd, 1H, J= 13.2 Hz), 4.96-4.90 (m, 1H), 4.67-4.61 (m, 2H), 4.12-4.09 (m, 2H) ppm. 19F-NMR (CDC13, 376 MHz): -77.87 ppm. _
Exam le P7: 4-r5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-2,5-dih^
Figure imgf000287_0001
A solution of 4-[5-(3,5-Dichloro-phenyl)-5 rifluoromethyl-2,5-dihydro-furan-3-yl]-2-methyl-benzoic acid (330 mg) was suspended in dichloromethane (4 mL). A catalytic amount of NN-dimethylformamide ("DMF") and oxalyl chloride (0.08 mL) were added to the suspension. The reaction mixture was stirred at ambient temperature for one hour. The reaction mixture was concentrated and the residue dissolved in dry tetrahydrofuran (4 mL). To the solution was added a solution of ammonium hydroxide (2 mL, 25%). The reaction mixture was stirred at ambient temperature for one hour. It was then quenched by addition of water and extracted with ethyl acetate. The organic extract was washed with water, dried over sodium sulfate and concentrated in vacuo. The crude residue was treated with Diisopropylether (ca 0.1 mL) and pentane (1 mL). The mixture was stirred at room temperature for 30 minutes then the precipitate was filtered, washed twice with pentane and dried under vacuo to give the title compound (308 mg) as a bright red solid. 'H-NMR (CDC13, 400 MHz): 7.49 (m, 3H), 7.48 (m, 1H), 7.27-7.21 (m, 2H), 6.38 (s, 1H), 5.74 (bs, 2H), 5.32 (dd, J= 2.2 and 12.4 Hz, 1H), 5.20 (bd, 1H, J= 12.2 Hz), 2.53 (s, 3H) ppm. 19F-NMR (CDC13, 376 MHz): -78.14 ppm.
Example P8 (compound A86 from Table A): (E)-4-[5-(3.5-Dichlorophenyl)-5-trifluoromethyl-2.5- ihydro-furan-3 -yl] -N- [(methoxyimino)methyll -2-methylbenzamide
Figure imgf000287_0002
A solution of 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl]-2-methyl-benzamide (lOOmg) and Ν,Ν-Dimethylformamide dimethylacetal (4.2mL) was refluxed under Argon for 30 min then the solution was concentrated in vacuo. The residue was dissolved in 1,4-dioxane (2 mL) and a solution of methoxyamin hydrochloride (56 mg) and sodium hydroxide (58 mg) in water (1.6 mL) and acetic acid (1.6 mL) was added. The solution was stirred at rt for one hour. It was then quenched by addition of water and extracted with methyl tert-butyl ether. The combined organic extracts were washed with brine, dried (Na2S04) and evaporated.
Flash Chromatography eluting with Cyclohexane:EtOAc afforded 78 mg of the title compound. 'H-NMR (CDCI3, 400 MHz): 8.5 (m, 1H), 7.8 (m, 1H), 7.55-7.48 (m, 3H), 7.40 (m, 1H), 7.32-7.25 (m, 3H), 6.42 (m, 1H), 5.32 (dd, 1H), 5.20 (bd, 1H), 3.9 (s, 3H), 2.53 (s, 3H) ppm. - 2δ6 -
Example P9 (compound D24 from Table D): 4-r5-(3,5-Dichloro-phenyl -5-trifluoromethyl-4,5-dihvdro- f ran-3-yll-N-(l.l-dioxo-llambda*6*-thietan-3-yl -2-methyl-benzamide
Figure imgf000288_0001
n-BuLi (15.7 mL, 1.5 equiv) was added dropwise to a solution of diisopropylamine (2.62 mL, 1.5 equiv) in tetrahydrofuran (40 mL) at 0°C un der argon. The reaction mixture was stirred for 10 min, and cooled down to -20°C. Then trimethylsilylpropyne (2.21 mL, 1.2 equiv) was added dropwise. The reaction mixture was then stirred at -20°C for 90 minutes. The reaction mixture was cooled down to -78°C, and 1- (3,5-Dichloro-phenyl)-2,2,2-trifluoroethanone (3 g, 12.35 mmol) in tetrahydrofuran (20 mL) was added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred for two hours 30 minutes. It was then quenched by addition of saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2S04) and evaporated. This crude residue was then redissolved in methanol (60 mL) and treated with potassium carbonate (3.4 g, 2 equiv). The reaction mixture was stirred for 3 h and then filtered and evaporated. Flash
Chromatography eluting with Cyclohexane:EtOAc (9/1) afforded 1.896 g (54%) of the title compound. 'H-NMR (CDCI3, 400 MHz): 7.51 -7.468 (m, 2H), 7.45-7.38 (m, 1H), 3.18-2.96 (m, 3H), 2.16-2.11 (m, 1H) ppm. "F-NMR (CDCI3, 376 MHz): -79.02 ppm. -(3 , 5 -Dichloro -phenyl) -5 -trifluoromethyl-dihydrofuran-3 -one
Figure imgf000288_0002
5-Bromo-l-oxy-nicotinic acid methyl ester (3.00 g, 1.5 equiv) (prepared according to AstraZeneca SB; AstraZeneca UK Ltd Patent WO2005/26149), triflimide (2.66 g, 1.1 equiv) and Ph3PAuNTf2 (338 mg, 2.5 mol %) were added in this order to a solution of 2-(3,5-Dichloro-phenyl)-l,l,l-trifluoro-pent-4-yn-2-ol (2.44 g, 8.6 mmol) in 1 ,2-dichloroethane (86 mL) under argon. The reaction mixture was left to stir at rt overnight. It was then concentrated in vacuo. Column chromatography eluting with cyclohexane:ethyl acteate (92/8) afforded 952 mg of the the expected compound (37%).
'H-NMR (CDCI3, 400 MHz): 7.46-7.40 (m, 3H), 4.37 (d, 1H), 4.24 (d, 1H), 3.26 (d, 1H), 2.87 (d, 1H) ppm. "F-NMR (CDCI3, 376 MHz): -79.42 ppm.
5
Step C: 4-[5-(3,5-Dichloro-phenyl)-3-hydroxy-5-trifluoromethyl-tetrahydro-furan-3-yl]-2-methyl-benzoic acid tert-butyl ester
Figure imgf000289_0001
To a solution of 4-Bromo-2-methyl-benzoic acid tert-butyl ester (234 mg, 1.2 equiv) under argon at - 10 100°C in tetrahydrofuran (2.6 mL) was added n-BuLi (0.62 mL, 1.2 equiv) dropwise over 5 min. The reaction mixture was left to stir for 20 min at -100°C. A solution of 5-(3,5-Dichloro-phenyl)-5- trifluoromethyl-dihydrofuran-3-one (215 mg, 0.72mmol) in 1.0 mL tetrahydrofurane was then added dropwise. It was stirred at this temperature for one hour. The reaction mixture was quenched with water and extracted with ethyl acetate. The combined organic extracts were then washed with brine, dried 15 (Na2S04) and evaporated. Column chromatography eluting with cyclohexane: ethyl acteate (9/1) afforded 62 mg (17 %) of the expected compound.
'H-NMR (CDCI3, 400 MHz): 7.77 (d, 1H), 7.52-7.32 (m, 3H), 7.22 (s, 1H), 7.15 (dd, 1H), 4.26 (d, 1H), 4.00 (d, 1H), 3.16 (dd, 1H), 2.95 (s, 1H), 2.81 (d, 1H), 2.54 (s, 3H), 1.58 (bs, 9H) ppm.
20 Step D: 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-furan-3-yl]-2-methylbenzoic acid tert- tyl ester
Figure imgf000289_0002
A solution of 4-[5 -(3 ,5 -Dichloro-phenyl)-3 -hydroxy-5 -trifluoromethyl-tetrahydro-furan-3 -yl] -2-methyl- benzoic acid tert-butyl ester (62 mg, 0.12 mmol) in dichloromethane (1.2 mL) under argon at -78°C was 25 treated with thionyl chloride (26 μL, 3 equiv) followed by triethylamine (0.13 mL, 7.5 equiv). The
reaction mixture was stirred at -78°C until complete consumption of starting material. It was quenched with water and extracted with EtOAc. The combined organic extracts were then washed with brine, dried (Na2S04) and evaporated. Column chromatography eluting with cyclohexane: ethyl acetate (95/5) afforded a mixture of the title compound and its isomer in a 3:2 ratio. Step D': 4-[5-(3,5-Dichloro-phenyl)-5 rifluoromethyl-4,5-dihydro-furan-3-yl]-2-ethylbenzoic acid tert- butyl ester A solution of trimethylsilyldiazomethane (0.74 mL, 2.0 M in Et20, 2.2 equiv) in dimethoxyethane (4 niL) under argon at -78°C was treated with MeLi (0.92 mL, 1.6 M in Et20, 2.2 equiv). After 15 min at -78°C, a solution of 4-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutyryl]-2-methylbenzoic acid tert-butyl ester (321 mg, 0.67 mmol) in dimethoxyethane (2+0.7mL) was added to the reaction mixture, which was stirred at -78°C for one hour and then warmed up to room temperature. It was left to stir at this temperature for 2h. It was then quenched by addition of AcOH (85 L, 2.2 equiv) and a 1M solution of TBAF in THF was added (2 mL, 3 equiv). The reaction mixture was left to stir overnight. It was quenched by addition of water and extracted with ethyl acetate. The combined organic layers were dried (Na2S04) and evaporated. Flash Chromatography eluting with cyclohexane: ethyl acetate (98/2) afforded 85 mg of the title compound (27%) as a light yellow oil which solidifies upon standing.
¾-NMR (CDCI3, 400 MHz): 7.79 (d, 1H), 7.52-7.45 (m, 2H), 7.43-7.37 (m, 1H), 7.08 (dd, 1H), 7.05 (s, 1H), 7.01 (s, 1H), 3.74 (dd, 1H), 3.31 (dd, 1H), 2.56 (s, 3H), 1.60 (bs, 9H) ppm. 19F-NMR (CDC13, 376 MHz): -80.85 ppm.
Similarly, 4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-furan-4-yl]-2-methyl-benzonitrile could be obtained when 4-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-butanoyl]-2-methyl-benzonitrile was used as a starting material.
¾-NMR (CDCI3, 400 MHz): δ = 7.53 (d, 1 H), 7.45-7.50 (m, 2 H), 7.37-7.45 (m, 1 H), 7.10-7.18 (m, 2 H), 7.02-7.10 (m, 1 H), 3.73 (dd, 1 H), 3.25-3.38 (m, 1 H), 2.48-2.54 (m, 3 H) ppm. 19F-NMR (CDC13, 376 MHz): -80.88 ppm.
Similarly, 4-(4-bromo-3-methyl-phenyl)-2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-furan could be obtained when 1 -(4-bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-butan-l - one was used as a starting material.
¾-NMR (CDCI3, 400 MHz): δ = 7.43-7.54 (m, 4 H), 7.41 (t, 1 H), 7.09 (d, 1 H), 6.83-6.96 (m, 2 H), 3.71 (dd, 1 H), 3.27 (d, 1 H), 2.39 (s, 3 H) ppm
"F-NMR (CDCI3, 376 MHz): -80.82 ppm
Ste E: 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-furan-3-yl] -2-methyl-benzoic acid
Figure imgf000290_0001
A solution of 4-[5-(3,5-Dichloro-phenyl)-5 rifluoromethyl-4,5-dihydro-furan-3-yl]-2 -methyl-benzoic acid tert-butyl ester (35 mg, 0.074 mmol) in dichloromethane (0.4 mL) at room temperature was treated with trifluoroacetic acid (0.055 mL, 10 equiv). The reaction mixture was stirred for 6 hours. The volatiles were removed in vacuo. Flash Chromatography eluting with cyclohexane: ethyl acetate (7/3) afforded 23 mg of the title compound (74%).
'H-NMR (CDCI3, 400 MHz): 8.03 (d, 1H), 7.52-7.46 (m, 2H), 7.45-7.39 (m, 1H), 7.16 (dd, 1H), 7.11 (s, 1H), 7.08 (s, 1H), 3.77 (dd, 1H), 3.33 (dd, 1H), 2.65 (s, 3H) ppm. "F-NMR (CDCI3, 376 MHz): -80.82 ppm. Step F: 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-furan-3-yl]-N-(l,l-dioxo-llambda*6*- thietan-3- l)-2-methyl-benzamide
Figure imgf000291_0001
4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-furan-3-yl]-2-methyl-benzoic acid (23 mg, 0.055 mmol) was dissolved in dichloromethane (0.6 mL), and oxalyl chloride (22 μL, 5 equiv) was added. One drop of dimethylforamide was added as a catalyst, and the reaction mixture was stirred at room temperature for 18 hours. Volatiles were evaporated to give the expected acid chloride. The residue was dissolved in dichloromethane. Triethylamine (17 μL, 2.2 equiv) followed by the trifluoroacetate salt of l,l-Dioxo-llambda*6*-thietan-3-ylamine (14 mg, 1.05 equiv) were added. The reaction mixture was then stirred at room temperature for 5 hours. The reaction was quenched by adding water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried (Na2S04) and evaporated. Flash Chromatography eluting with cyclohexane: ethyl acetate (7/3) afforded the title compound.
'H-NMR (CDCI3, 400 MHz): 7.51 -7.47 (m, 2H), 7.42 (t, 1H), 7.36 (d, 1H), 7.13-7.07 (m, 2H), 7.03-6.98 (m, 1H), 6.46 (d, 1H), 4.94-4.74 (m, 1H), 4.63-4.58 (m, 2H), 4.07-3.98 (m, 2H), 3.74 (dd, 1H)3.31 (dd, 1H), 2.46 (s, 3H) ppm. 19F-NMR (CDC13, 376 MHz): -80.87 ppm. m.p.= 211 -213°C.
Similarly, 4 2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-furan-4-yl]-2-methyl-N-[(4R)-3- oxo-2-(2,2,2-trifluoroethyl)isoxazolidin-4-yl]benzamide (D25) could be prepared. 1H NMR (CDCI3 ,400MHz): δ = 7.44 - 7.56 (m, 2 H), 7.35 - 7.44 (m, 2 H), 7.03 - 7.13 (m, 2 H), 7.01 (s, 1 H), 6.33 (d, J=4.4 Hz, 1 H), 4.99 - 5.07 (m, 1 H), 4.93 (d, J=4.4 Hz, 1 H), 4.01 - 4.31 (m, 3 H), 3.74 (dd, J=15.0, 2.2 Hz, 1 H), 3.30 (d, J=15.8 Hz, 1 H), 2.47 ppm (s, 3 H).
Similarly, 4 2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-furan-4-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide (D26) could be prepared. 1H NMR (CDC13 ,400MHz): δ = 7.49 (d, J=1.5 Hz, 2 H), 7.42 (dt, J=3.9, 2.2 Hz, 2 H), 7.03 - 7.14 (m, 2 H), 7.00 (s, 1 H), 6.38 29Q
(d, J=3.7 Hz, 1 H), 4.94 - 5.04 (m, 1 H), 4.04 (dd, J=1 1.0, 8.4 Hz, 1 H), 3.54 - 3.78 (m, 3 H), 3.32 (d, 1 H), 2.47 (s, 3 H), 1.27 ppm (t, J=7.2 Hz, 4 H).
Exam le P10: 4-f3.5-Dichloro-phenyl -5.5.5-trifluoro-4-hydroxy-pent-2-ynoic acid methyl ester
Figure imgf000292_0001
Step A:
To a solution of 4-(3,5-Dichloro-phenyl)-5,5,5-trifluoro-pent-2-yne-l,4-diol (1.8 g) in acetone (90 mL) at 0°C was slowly added a solution of Jones' reagent (9 mL), under argon. The solution became brown and after 90 minutes, more Jone's reagent (0.8 mL) was added at 0C. The solution was stirred for another 4 hours then it was diluted with water. The mixture was extracted with ethyl acetate, washed with a solution of sodium metabisulfite, dried over magnesium sulphate and concentrated to give 4-(3,5-Dichloro- phenyl)-5,5,5-trifluoro-4-hydroxy-pent-2-ynoic acid (1.839 g) as a colorless oil. 19F-NMR (CDC13, 376 MHz): -79.61 ppm.
Step B:
To a stirring solution of 4-(3,5-Dichloro-phenyl)-5,5,5-trifluoro-4-hydroxy-pent-2-ynoic acid (1.345 g) in toluene/MeOH (27 and 9 mL) under argon at 0°C was slowly added a solution of TMSCHN2 (3.3 mL, 2M in hexane). The reaction was exothermic and some gas evolution was observed. The solution was stirred for 4 hours at 0C then acetic acid (2 mL) was added. The solvent was then evaporated in vacuo to give a crude residue. The residue was purified by chromatography on silica gel (eluent: heptane / ethyl acetate 1 :0 to 8:2) to give 4-(3,5-Dichloro-phenyl)-5,5,5-trifluoro-4-hydroxy-pent-2-ynoic acid methyl ester (1.2 g) as a white solid. 'H-NMR (CDC13, 400 MHz): 7.60 (m, 2H), 7.46 (s, 1H), 3.87 (s, 3H) ppm. Example PI 1 : 2-Methyl-4-(boronic acidVbenzoic acid tert-butyl ester
Figure imgf000292_0002
Step A:
To a solution of 4-Bromo-2-methyl-benzoic acid tert-butyl ester (5g) in DMF (70 mL) then
4,4,5,5,4',4',5',5'-Octamethyl-[2,2']bi[[l,3,2]dioxaborolanyl] (4.68 g) , potassium acetate (5.43 g) and palladium acetate (124 mg) were successfully added. The reaction mixture was stirred at room temperature for 2 days then more palladium acetate (124 mg) was added and the mixture was stirred at 80°C. After 6 hours, more palladium acetate (124 mg) was added and the reaction mixture was stirred at 80°C for 18 hours. Then 4,4,5,5,4',4',5',5'-Octamethyl-[2,2']bi[[l,3,2]dioxaborolanyl] (2.35 g), potassium acetate (2.7 g) and palladium acetate (124 mg) were added again to the reaction mixture. After stirring at 80°C for 6 hours, more palladium acetate (250 mg) was added and the reaction mixture was stirred at 80°C for 18 hours. The reaction mixture was then allowed to cool to room temperature and was diluted with ethyl acetate. The organic layer was washed with brine and HC1 1 N. It was then dried over magnesium sulfate, filtered, and concentrated in vacuo to give a crude residue that was used as such in the following step.
Step B:
To a solution of 2-Methyl-4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-benzoic acid tert-butyl ester (1.6 g) in water/acetone (16/32mL) at room temperature, was added ammonium acetate (1.02 g) then sodium periodate (3.1 g). The reaction was stirred at rt for 5 hours then was diluted with ethyl acetate and I N HC1 solution. The aqueous solution was extracted with ethyl acetate. The combine organic solutions were dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by chromatography on silica gel (eluent: heptane\ethyl acetate, 1 : 1) to give 2-Methyl-4-(boronic acid)- benzoic acid tert-butyl ester (750 mg) as a white solid. 'H-NMR (CDC13, 400 MHz): 7.82 (d, J= 7.70 Hz, 1H), 7.59-7.57 (m, 2H), 2.59 (s, 3H), 1.60 (s, 9H) ppm.
Example P12: 4-r5-(3,5-Dichloro-phenyl)-2-oxo-5-trifluoromethyl-2,5-dihvdro-furan-3-yl1-2-methyl-
Figure imgf000293_0001
To a solution of 4-(3,5-Dichloro-phenyl)-5,5,5-trifluoro-4-hydroxy-pent-2-ynoic acid methyl ester (690 mg) and 2-Methyl-4-(boronic acid)-benzoic acid tert-butyl ester (750 mg) in 1,4-dioxane (lOmL) under argon, was successively added acetic acid (0.01 mL), palladium acetate (16 mg) and \x\{tert- butyl)phosphine (0.03 mL). The reaction was refluxed under argon for 1 hour then stirred at room temperature for 18 hours. Then more palladium acetate (17 mg), tri(tert-butyl)phosphine (0.03 mL) and acetic acid (0.04 mL) were added. The reaction was refluxed for 4 hours then more palladium acetate (20 mg) was added. A Tricyclohexylphosphine solution (0.18 mL, 20 wt. % in toluene) was added and the solution was refluxed for 45 min. More 2-Methyl-4-(boronic acid)-benzoic acid tert-butyl ester (200 mg) was then added and the reaction was stirred at room temperature for 18 hours. It was then refluxed for 2 hours and then allowed to cool to room temperature. The reaction was concentrated under vacuo. The crude residue was purified by chromatography on silica gel (eluent: heptanes\dichloromethane, 7:3) to give 4-[5-(3,5-Dichloro-phenyl)-2-oxo-5-trifluoromethyl-2,5-dihydro-furan-3-yl]-2-methyl-benzoic acid ^ tert-butyl ester (499 mg) as an colorless oil. 'H-NMR (CDCI3, 400 MHz): 7.89 (d, J= 8.07 Hz, 1H), 7.80 (s, 1H), 7.76 (m, 2H), 7.54 (m, 2H), 7.49 (m, 1H), 2.62 (s, 3H), 1.61 (s, 9H).
Example PI 3: 4-[5-(3.5-Dichloro-phenylV2-oxo-5 rifluoromethy^
Figure imgf000294_0001
To a solution of 4-(3,5-Dichloro-phenyl)-5,5,5-trifluoro-4-hydroxy-pent-2-ynoic acid methyl ester (200 mg) and tributylamine (0.49 mL) in DMF (1.2 mL) under argon, was successively added 4-Iodo-2- methyl-benzoic acid methyl ester (404 mg), palladium acetate (14 mg), Tri(o-tolyl)phosphine (36 mg). After 30 min, formic acid (0.06 mL) was added. The reaction was stirred under argon then heated at 70C for one hour. The reaction was quenched by addition of water and EtOAc. The mixture was extracted with diethyl ether, water, dried over magnesium sulfate, filtered and concentrated under vacuo. The crude residue was purified by chromatography on silica gel (eluent: heptanes\diethyl ether, 7:3) to give 4-[5- (3,5-Dichloro-phenyl)-2-oxo-5-trifluoromethyl-2,5-dihydro-furan-3-yl]-2-methyl-benzoic acid methyl ester (84 mg) as an orange oil. 'H-NMR (CDC13, 400 MHz): 7.99 (d, J= 8.80 Hz, 1H), 7.83 (s, 1H), 7.76 (m, 2H), 7.54 (m, 2H), 7.49 (m, 1H), 3.93 (s, 3H), 2.66 (s, 3H) ppm.
Exam le P14: Preparation of 2-Chloro-6-iodo-nicotinic acid methyl ester
Figure imgf000294_0002
Step A:
2-(Dimethylamino)-ethanol (20.5 mL) was dissolved in Hexane (150 mL) and the solution was stirred under argon and cooled to -5°C. n-Butyl Lithium (184 mL, 2.5 M in hexanes) was added dropwise at - 5°C and further stirred at 0°C for 45 min. The solution was then cooled to -75°C and a solution of 2- Chloro-3-methyl-pyridine (9.78 g) in hexane (150 mL) was added dropwise. The orange solution was stirred at -75°C for two hours then a solution of iodine (78 g) in tetrahydrofuran (540 mL) was added dropwise at -75°C. After stirring for 2 hours, the solution was allowed to warm slowly at room temperature and stirred over night. The reaction mixture was then cooled to 0°C and 50 ml water was added dropwise added. The solution was then extracted with diethyl ether. The organic layers were combined, dried over magnesium sulfate, filtered and concentrated under vacuo. The crude residue was purified by chromatography on silica gel (eluent: heptane\dichloromethane, 3:1) to give 2-Chloro-6-iodo- 3-methyl-pyridine (16 g) as a brown solid. 'H-NMR (CDC13, 400 MHz): 7.53 (d, J= 7.70 Hz, 1H), 7.19 (d, J= 7.34 Hz, 1H), 2.33 (s, 3H) ppm.
Step B:
2-Chloro-6-iodo-3-methyl-pyridine (12 g) was suspended in water (250 mL) then potassium
permanganate (18g) was added. The solution was re fluxed for 18 hours then the mixture was cooled to room temperature and filtered through Hyflo. The mixture was extracted with methyl tert-butyl ether. The aqueous layer was then acidified with HC1 1M to pH 2 and extracted with ethyl acetate. The organic layers were combined, dried over magnesium sulfate, filtered and concentrated to give 2-Chloro-6-iodo- nicotinic acid (4.32 g) as a white solid. 'H-NMR (CD3OD, 400 MHz): 7.91 (d, J= 7.70 Hz, 1H), 7.87 (d, J= 8.07 Hz, 1H) ppm.
Step C:
2-Chloro-6-iodo-nicotinic acid (3 g) was suspended in dichloromethane (40 ml). A catalytic amount of NN-dimethylformamide ("DMF") and oxalyl chloride (1.1 ml) were added to the suspension. The reaction mixture was stirred at ambient temperature for 1.5 hours then methanol (2 mL) was added. The reaction mixture was stirred for 30 minutes than water was added to the reaction. The mixture was extracted with methyl tert-butyl ether. The organic extract was washed with brine, dried over sodium sulfate and concentrated to give 2-Chloro-6-iodo-nicotinic acid methyl ester (3.1 g) as a brown solid. lH- NMR (CDC13, 400 MHz): 7.78 (m, 2H), 3.96 (s, 3H) ppm. Example PI 5: 5-r5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-2,5-dihvdro-furan-3-yl1-2-fluoro- benzonitrile
Figure imgf000295_0001
To a solution of Tributyl-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan- 3-yl]-stannane (300 mg) in NN-dimethylformamide (12 mL) under argon was successively added 2- Fluoro-5-iodo-benzonitrile (630 mg), copper iodide (20 mg) and then tetrakis(triphenylphosphine) palladium (42 mg). The reaction was heated at lOOC under argon for 20 hours. The reaction was allowed to cool down to room temperature then water was added and the mixture was extracted with ethyl acetate. The organic extract was washed with water, dried over sodium sulfate and concentrated in vacuo to give a residue which was purified by chromatography on silica gel (eluent: heptanes\dichloromethane, 2: 1) to ^ give 5-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl] -2-fluoro-benzonitrile (182 mg) as a brown solid.
¾-NMR (CDCI3, 400 MHz): 7.65-7.63 (m, 2H), 7.47 (m, 2H), 7.40 (m, 1H), 7.29 (m, 1H), 6.40 (bs, 1H), 5.30 (dd, J= 2.2 and 12.8 Hz, 1H), 5.17 (m, 1H) ppm. "F-NMR (CDCI3, 376 MHz): -78.11 and -104.17 ppm.
Similarly, 2-Chloro-6-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl] -nicotinic acid methyl ester could be prepared using 2-Chloro-6-iodo-nicotinic acid methyl ester as a coupling partner. ¾-NMR (CDCI3, 400 MHz): 8.21 (d, 1H, J= 8.07 Hz), 7.49 (m, 2H), 7.39-7.37 (m, 2H), 6.82 (m, 1H), 5.40 (dd, J= 2.57 and 13.2 Hz, 1H), 5.28 (m, 1H), 3.97 (s, 3H) ppm. "F-NMR (CDCI3, 376 MHz): -77.87 ppm
Similarly, 6-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl]-2-methyl-nicotinic acid ethyl ester could be prepared using 6-Bromo-2-methyl-nicotinic acid ethyl ester as a coupling partner. lH- NMR (CDCI3, 400 MHz): 8.21 (d, 1H, J= 8.07 Hz), 7.50 (m, 2H), 7.38 (m, 1H), 7.31 (m, 1H), 6.73 (m, 1H), 5.42 (dd, J= 2.57 and 13.2 Hz, 1H), 5.30 (m, 1H), 4.39 (q, J = 6.97 Hz, 2H), 2.82 (s, 3H), 1.42 (t, J = 6.97 Hz, 3H) ppm. 19F-NMR (CDC13, 376 MHz): -77. 94 ppm
Similarly, 4-(3-Chloro-4-methyl-phenyl)-2-(3,5-dichloro-phenyl)-2-trifluoromethyl-2,5-dihydro-furan could be prepared using 2-Chloro-4-iodo-l -methyl -benzene as a coupling partner. 'H-NMR (CDCI3, 400 MHz): 7.48 (m, 2H), 7.37 (m, 2H), 7.25 (m, 1H), 7.16 (m, 1H), 6.31 (m, 1H), 5.28 (dd, J= 2.57 and 12.47 Hz, 1H), 5.16 (m, 1H), 2.40 (s, 3H) ppm. 19F-NMR (CDC13, 376 MHz): -78.19 ppm.
Similarly, 5-Bromo-2-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl]-4-methyl- pyridine could be prepared using 5-Bromo-2-iodo-4-methyl-pyridine as a coupling partner. 'H-NMR (CDCI3, 400 MHz): 8.61 (s, 1H), 7.49 (m, 2H), 7.38 (m, 1H), 7.32 (m, 1H), 6.64 (m, 1H), 5.38 (dd, J= 2.20 and 13.2 Hz, 1H), 5.27 (m, 1H), 2.43 (s, 3H) ppm. "F-NMR (CDCI3, 376 MHz): -78.07 ppm
Similarly, 6-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl]-nicotinic acid methyl ester could be prepared using 6 -Bromo -nicotinic acid methyl ester as a coupling partner. 'H-NMR
(CDCI3, 400 MHz): 9.18 (m, 1H), 8.31 (m, 1H), 7.54 (m, 1H), 7.50 (m, 2H), 7.38 (m, 1H), 6.78 (m, 1H), 5.45 (dd, J= 2.20 and 13.2 Hz, 1H), 5.32 (m, 1H), 3.98 (s, 3H) ppm. "F-NMR (CDCI3, 376 MHz): -77.94 ppm ^
Example P16: (compound Gl from Table G): 5-r5-(3,5-Dichloro-phenyl -5-trifluoromethyl-2,5-dihvdro-
Figure imgf000297_0001
solution of 5-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-2,5-dm^
(82 mg) in acetonitrile (3 mL) was successively added potassium carbonate (62 mg) and 1H-
[l ,2,4]Triazole (40 mg). The reaction was heated at 80C for 5 hours. The reaction was allowed to cool down to room temperature then the suspension was filtered. The filtrate was concentrated under vacuo to give a residue which was purified by chromatography on silica gel (eluent: ethyl acetate\dichloromethane, 4: 1) to give 5-[5-(3,5-Dichloro-phenyl)-5 rifluoromethyl-2,5-dihydro-furan-3-yl]-2-[l ,2,4]triazol-l -yl- benzonitrile (74 mg) as a white foam.
'H-NMR (CDCI3, 400 MHz): 8.86 (bs, 1H), 8.22 (bs, 1H), 7.88 (d, J= 8.44 Hz, 1H), 7.82 (bs, 1H), 7.77 (m, 1H), 7.49 (s, 2H), 7.41 (m, 1H), 6.54 (bs, 1H), 5.37 (dd, J= 2.2 and 12.8 Hz, 1H), 5.24 (d, J= 12.4 Hz, 1H) ppm. "F-NMR (CDCI3, 376 MHz): -78.00 ppm. Similarly, 2-(4-Bromo-pyrazol-l -yl)-5-[5-(3,5-dichloro-phenyl)-5 rifluoromethyl-2,5-dihydro-furan-3- yl] -benzonitrile (compound G2 from Table G) was obtained using 4-Bromo-lH-pyrazole as a
nucleophile. 'H-NMR (CDCI3, 400 MHz): 8.86 (bs, 1H), 8.22 (bs, 1H), 7.88 (d, J= 8.44 Hz, 1H), 7.82 (bs, 1H), 7.77 (m, 1H), 7.49 (s, 2H), 7.41 (m, 1H), 6.54 (bs, 1H), 5.37 (dd, J= 2.2 and 12.8 Hz, 1H), 5.24 (d, J= 12.4 Hz, 1H) ppm. "F-NMR (CDCI3, 376 MHz): -78.03 ppm.
Example PI 7: 2-Chloro-6-r5-(3,5-dichloro-phenyl)-5-trifluoromethyl-2,5-dihvdro-furan-3-yl1-nicotinic acid
Figure imgf000297_0002
solution of 2-Chloro-6-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl]-nicotinic acid methyl ester (280 mg) in tetrahydrofuran/water ( 1 .4 mL of each) was added lithium hydroxyde (30 mg). The reaction mixture was stirred at room temperature for 24 hours. The solution was then diluted by addition of water and extracted with methyl tert-butyl ether. The aqueous extract was acidified with a solution of hydrochloric acid (1M) and extracted with dichloromethane. All the organic phases were gathered, dried over sodium sulfate and concentrated in vacuo to give 4-[5-(3,5-Dichloro-phenyl)-5- trifluoromethyl-2,5-dihydro-furan-3-yl] -2-methyl-benzoic acid (190 mg) as a white foam. ,
- 296 -
'H-NMR (CDCI3, 400 MHz): 8.37 (d, J= 8.08 Hz, 1H), 7.50 (m, 2H), 7.44 (d, J= 8.07 Hz, 1H), 7.39 (t, J= 1.4 Hz, 1H), 6.87 (m, 1H), 5.42 (dd, J= 2.2 and 13.2 Hz, 1H), 5.29 (m, 1H) ppm.
Similarly, 6-[5-(3,5-Dichloro-phenyl)-5 rifluoromethyl-2,5-dihydro-furan-3-yl]-2-methyl-nicotinic acid was obtained from the hydrolysis of 6-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3- yl]-2-methyl-nicotinic acid ethyl ester. "F-NMR (CDCI3, 376 MHz): -77.91 ppm.
Similarly, 6- [5 -(3 ,5 -Dichloro-phenyl)-5 -trifluoromethyl-2,5 -dihydro-furan-3 -yl] -nicotinic acid was obtained from the hydrolysis of 6-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl]- nicotinic acid methyl ester. "F-NMR (CDCI3, 376 MHz): -77.92 ppm.
Similarly, 4-[5-(3,5-Dichloro-phenyl)-2-oxo-5-trifluoromethyl-2,5-dihydro-furan-3-yl]-2-methyl-benzoic acid was obtained from the hydrolysis of 4-[5-(3,5-Dichloro-phenyl)-2-oxo-5-trifluoromethyl-2,5- dihydro-furan-3-yl]-2-methyl-benzoic acid methyl ester. "F-NMR (CDCI3, 376 MHz): -76.42 ppm.
Example P18: Preparation of 2-ri-r4-r2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-furan-4- yllphenyl] ethyllisoindoline- 1 ,3 -dione
Figure imgf000298_0001
Step A: Preparation of 2-(3,5-dichlorophenyl)-l,l,l-trifluoro-but-3-en-2-ol
Figure imgf000298_0002
Vinylmagnesium bromide 1M in THF (216.2 mL, 216.20 mmol) was added to a solution of 1 -(3,5- dichlorophenyl)-2,2,2-trifluoro-ethanone (51.50g, 211.93 mmol) in dry THF (425 mL) slowly at -75°C to -65°C. The reaction mixture was allowed to warm to room temperature, and stirred at rt overnight. It was quenched by pouring into 2M aqueous HC1 (140mL) and extracted three times with diethyl ether. The combined organic fractions were washed successively with saturated NaHC03 solution, water, and brine and dried (MgSO i). The solution was filtered and the solvent was removed under reduced pressure. Vacuum distillation (80-85°C /l mbar) of the residue afforded 53.34 g (92.6 %) of the title compound as a clear colorless liquid.
¾-NMR (400 MHz, CDC13): δ 2.61 (s, 1H, OH), 5.57 (d, J= 11 Hz, 1H), 5.62 (d, J= 17.2Hz, 1H), 6.36 (dd, J7= 17.2Hz, J2=l lHz, 1H), 7.37 (t, J= 1.8Hz, 1H), 7.46-7.50 (m, 2H) ppm.
"F-NMR (377 MHz, CDC13): δ -78.80 ppm.
Ste B: Preparation of 5-(3,5-dichlorophenyl)-5-(trifluoromethyl)tetrahydrofuran-2-ol
Figure imgf000299_0001
Rh(CO)2acac (0.0048 g, 0.018 mmol) and 6-diphenylphosphanyl-lH-pyridin-2-one (0.026 g, 0.09mmol) were dissolved in toluene (80 mL) under argon. 2-(3,5-dichlorophenyl)-l , l ,l- trifluoro-but-3-en-2-ol (5 g, 18.45mmol) was added and the reaction mixture was then transferred into a mechanically stirred stainless steel autoclave (300mL). The autoclave was purged three times with hydrogen (5 bar), pressurized with hydrogen and carbon monoxide to 20 bar (CO/H2 composition = 1 : 1). The reaction was vigorously stirred and heated (80°C) for 22h. The reaction was stopped by cooling the autoclave to RT, venting and purging with argon. The reaction mixture was evaporated in vacuum and the product was isolated by column
chromatography (n-heptane/AcOEt gradient) as a brown gum in 5.0 g (1 1.13 mmol, 60%) yield. !HNMR (CDC13, 400 MHz): δ 2.45-2.08 (m, 4H); 2.80-2.61 (m, 3H); 5.67 (d, 1H, J=4.8Hz); 5.75 (d, 1H, J=4.8 Hz); 7.38-7.23 (m, 6H) ppm.
Step C: Preparation of 2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-furan
Figure imgf000299_0002
A mixture of 5-(3,5-dichlorophenyl)-5-(trifluoromethyl)tetrahydrofuran-2-ol (5g, 1 1.1 mmol) and pyridinium 4-toluenesulfonate (1.68 g, 6.68 mmol) was heated to and finally distilled using a kugelrohr distillation apparatus (150°C, vacuum 100 to 4 mbar). The desired product was obtained as a white solid (2.41g, 8.51mmol, 76%).
!HNMR (CDCls, 400 MHz): δ 2.95 (d, 1H, J=15.8Hz); 3.40(d, 1H, J=15.8Hz); 5.03(d, 1H, J=2.6Hz); 6.43(d, 1H,J= 2.6Hz); 7.43(s, 2H), 7.39(s, 1H) ppm.
Step D: Preparation of 4,5-dibromo-2-(3,5-dichlorophenyl)-2-(trifluoromethyl)tetrahydrofuran
Figure imgf000300_0001
A solution of bromine (1.13 g, 0.363 mL, 7.07 mmol) in dichloromethane (0.4 ml) was added to a solution of 2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-furan (2.00 g, 7.07 mmol) in dichloromethane (56 mL) slowly at -75°C under argon. The reaction mixture was allowed to warm to room temperature and stirred for additional 20 minutes. Then, the reaction mixture was poured in a Na2S203 aqueous solution and extracted twice with dichloromethane. The collected organic layers were dried (Na2S04), filtered and evaporated under reduced pressure to give the title product (7.05 mmol, 3.12 g, 99%) as a white solid.
'HNMR (CDC13, 400 MHz): δ 2.93 (d, 1H, J=14.7Hz); 3.62 (dd, 1H, J=5.5Hz, J=14.7Hz); 4.9 (d, 1H, 5.5Hz); 6.76(s, 1H); 7.49(m, 3H) ppm.
Step E: Preparation of 4-bromo-2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-furan
Figure imgf000300_0002
l,8-Diazabicyclo[5.4.0]undec-7-ene (0.103 g, 0.101 mL, 0.68 mmol) was dropwise added to a solution of 4,5-dibromo-2-(3,5-dichlorophenyl)-2-(trifluoromethyl)tetrahydrofuran (0.150 g,0.34 mmol) in Ν,Ν-dimethylformamide (1 mL) at room temperature under argon. Then, the reaction mixture was warmed to 100°C and stirred at that temperature for 20min. The reaction mixture was quenched by pouring into a 2M HC1 solution and extracted with n-hexane (3 times). The organic phase was dried (Na2S04) and evaporated under reduce pressure giving the title compound (75 mg, 0.207mmol, 61 >) as a yellow oil.
!HNMR (CDC13, 400 MHz): δ 3.15 (d, 1H, J=15.8Hz); 3.56 (dd, 1H, J,= 15.8Hz, J2= 2.6Hz); 6.51 (t, lH, J=2.2Hz); 7.39 (s, 1H); 7.41(t, 2H, J=1.5Hz) ppm. Step F: Preparation of 2-[l-[4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl] ethyljisoindoline- 1 ,3 -dione
Figure imgf000301_0001
Pd(DPPF)Cl2.CH2Cl2 (0.03957 g, 0.048 mmol) and potassium acetate (0.48 g, 4.85 mmol) were added to a solution of 2-[l-(4-bromophenyl)ethyl]isoindoline-l,3-dione (0.8 g, 2.423 mmol) and pinacol diborane (0.738 g, 2.91 mmol) in Ν,Ν-dimethylformamide ( 7 mL). The reaction mixture was stirred at 90°C for 12h under argon. The reaction mixture was diluted with water and ethyl acetate. Organic phase was washed 4 times with water and once with brine. It was dried and concentrated in vacuum. The crude material was purified by column chromatography (n-heptane / ethyl acetate gradient). The title product was obtained as a white solid (536mg, 1.42mmol, 59%).
'HNMR (CDCI3, 400 MHz): δ 1.32 (s, 12H); 1.93 (d, 3H, J=7.3Hz); 5.59 (q, 1H, 7.3Hz); 7.5 (d, 2H,J= 7.7Hz); 7.93-7.76(m, 4H) ppm.
Step G: Preparation of 2-[l-[4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-furan-4- yl]phenyl] ethyljisoindoline- 1 ,3 -dione
Figure imgf000301_0002
A test tube containing a magnetic stir bar was charged with S-Phos palladacycle catalysts (CAS = 1028206-58-7, STREM = 46-0269) (0.018 g, 0.0026 mmol); 2-[l-[4-(4,4,5,5-tetramethyl- 1, 3, 2-dioxaborolan-2-yl)phenyl]ethyl]isoindo line- 1,3 -dione (0.06232 g, 0.16 mmol) and potassium phosphate (0.055619 g, 0.26 mmol). The tube was capped with a rubber septum, evacuated and backfilled with argon (this sequence was repeated three times). Deionized water (0.02 mL) and dry toluene (0.4 mL) and were added sequentially and the resulting mixture was stirred at room temperature for ~2 min. 4-bromo-2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H- furan (0.046 g, 0.13 mmol) was added dropwise via syringe. The reaction mixture was stirred ^QQ vigorously at 100 °C for 18h. The reaction mixture was diluted with AcOEt, washed with water, dried (Na2S04) and evaporated. The residue was purified by flash chromatography on silica gel (n-heptane/ethyl acetate gradient 9: 1 to 5:5) to giving the title compound (0.034mmol, 18mg, 27%) as a white solid.
'HNMR (CDCI3, 400 MHz): δ 3.62 (dt, 1H, J,=15.3, J2= 2.2Hz); 5.47(q, 1H, J=7.3Hz); 6.83(s, 1H); 7.1 l(d, 2H, J=8.4Hz); 7.3 l(t, lH, J=1.8Hz); 7.37(s, 1H); 7.39(m, 3H); 7.61(m, 2H);
7.72(m, 2H) ppm.
Example P19: Preparation of 4-r(2S)-2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-furan-4-yl1- N-(l,l-dioxothietan-3- l)-2-methyl-benzamide (compound D24*)
Figure imgf000302_0001
Step A: 2-Methyl-4-trimethylsilanylethynyl-benzoic acid tert-butyl ester
Figure imgf000302_0002
To a solution of tert-butyl 4-bromo-2-methyl-benzoate (lOOg, 368.8 mmol) in tetrahydrofuran (6 mL/mmol) and diisopropylamine (1.2 equiv., 442.5 mmol) at room temperature were added copper(I)-iodide (0.05 equiv., 18.44 mmol) and dichlorobis(triphenylphosphine)palladate(II) (0.05 equiv., 18.44 mmol). Argon was bubbled through the reaction for 5 minutes then ethynyl(trimethyl)silane (2.2 equiv., 811.3 mmol) was added dropwise over a 15 min period. The mixture was heated at 45°C for 4h. The mixture was filtered over celite and the filter cake washed with ethyl acetate. The organic phase was then washed twice with a saturated NH4C1 solution and once with brine, dried over Na2S04 and solvents were evaporated under reduced pressure. The brown oil residue was purified over a silica gel column (eluent: cyclohexane / EtOAc) to give 40g of as a yellow oil. LCMS (Method A) 1.40 min; 1H-NMR (CDC13, 400 MHz): 0.25 (s, 3H), 1.61 (s, 9H), 2.52 (s, 3H), 7.30 (s, 1H), 7.32 (d, 1H), 7.74 (d, 1H).
Step B: 4-Ethynyl-2-methyl-benzoic acid tert-butyl ester
Figure imgf000303_0001
To a solution of tert-butyl 2-methyl-4-(2-trimethylsilylethynyl)benzoate (103.0 g, 357.0 mmol) in methanol (500 mL) at room temperature was added potassium carbonate (75.09g, 535.5 mmol). The resulting suspension was rapidly stirred at room temperature for 15min and then water was added until dissolution of K2C03. The mixture was extracted twice with
dichloromethane. The combined organic phases were washed with brine, dried over MgS04 and solvent were evaporated under reduced pressure. The crude product was purified over a silica gel column (eluent: heptane / EtOAc) to give 82 g of tert-butyl 4-ethynyl-2-methyl-benzoate as a yellow oil. LCMS (Method A) RT 1.18 min; 1H-NMR (CDC13, 400 MHz): 1.62 (s, 9H), 2.57 (s, 3H), 3.18(s, 1H), 7.29 (s, 1H), 7.38 (d, 1H), 7.80 (d, 1H).
Step C: tert-butyl 4-[(3R)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-but-l-ynyl]-2- meth l-benzoate
Figure imgf000303_0002
To a stirred solution of quinine (0.2 equiv., 16.5 mmol), barium(2+) dihydrofluoride (0.2 equiv., 16.46 mmol) and tert-butyl 4-ethynyl-2-methyl-benzoate (2.5 equiv., 205.8mmol) was added slowly dimethylzinc (4.0 equiv., 329.2 mmol, 2.0 mol/L) and the mixture was stirred at room temperature overnight. Tetraisopropoxytitanium (4 equiv., 329.2mmol) was then added and stirring was continued for another 3 hours to give an orange solution. Then, the solution was treated with l-(3,5-dichlorophenyl)-2,2,2-trifluoro-ethanone (20 g, 82.30 mmol) in one portion. The reaction mixture was stirred at room temperature for 3 days. The reaction mixture was quenched carefully with NH4C1 sat aqueous solution at 0°C, then allowed to stir at room temperature for 20 min. The toluene phase was then filtered over celite. The aqueous phase was extracted twice with ethyl acetate and each time the organic phases were filtered over celite. Finally, the ethyl acetate phases were grouped, washed once with brine, dried over magnesium sulfate and solvents were removed under reduced pressure. The crude product was purified over a silica gel column (eluent: heptane / EtOAc) to give 33.4g of expected tert-butyl 4-[3-(3,5- dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-but-l-ynyl]-2-methyl-benzoate) as a colorless oil. 3Q2
LCMS (Method A) RT 1.37 min, [M+H]+ 457/459/460; 1H-NMR (CDC13, 400 MHz): 1.60 (s, 9H), 2.55 (s, 3H), 3.64 (s, 1H, OH), 7.27 (s, 1H), 7.33(d, 1H), 7.41 (s, 1H), 7.68 (m, 2H), 7.79 (d, 1H). 119F-NMR (CDC13, 376.3 MHz):-80.05. Chiral HPLC analysis:
Column: Daicel CHIRALPAK® IB, 3μιη, 0.46cm x 10cm
Mobile phase: Hept/DCM 50/50
Flow rate: 1.0 ml/min
2 isomers were detected: rt= 1.94 min (86.2%) 2.28 min. (13.8%).
Step D: tert-butyl 4-[(E,3S)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-but-l-enyl]-2- meth l-benzoate
Figure imgf000304_0001
To a solution of tert-butyl 4-[(3R)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-but-l-ynyl]- 2-methyl-benzoate (43.0 g, 93.6 mmol) in 400 mL of toluene and 20 mL of THF cooled to - 40°C, sodium bis (2-methoxyethoxy)aluminum hydride (70 mass%> in Toluene) (Approx. 3.5 M) (2.0 equiv., 187.0 mmol) was added dropwise keeping the reaction below -30°C (gas- evolution). The reaction was stirred at -40°C for 1 h. The reaction mixture was carefully quenched first with acetone (10 mL) at -40°C and then with NH4C1 solution sat at -10°C and extracted twice with ethyl acetate. The combined organic layers were dried (MgS04), filtered and evaporated to give a colorless oil. The crude product was purified over a silica gel column (eluent: cyclohexane / EtOAc) to give 5.25g of tert-butyl 4-[(E)-3-(3,5-dichlorophenyl)-4,4,4- trifluoro-3-hydroxy-but-l-enyl] -2-methyl-benzoate as a colorless oil. LCMS (Method A) RT 1.35 min, [M+H]+ 459/461/462; 1H-NMR (CDC13, 400 MHz): 1.6 (s, 9H), 2.57 (s, 3H), 2.80 (s, 1H), 6.75 (dd, 2H), 7.25 (m, 2H), 7.49 (m, 1H), 7.53 (m, 2H), 7.8 (d, 1H). 19F-NMR (CDC13, 376.3 MHz):-79.4.
Step E: 4-[(2S)-2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-furan-4-yl]-2-methyl -benzoic acid
Figure imgf000305_0001
A homogeneous solution of [Rh(CO)2acac] (0.01 equiv., 0.009 mmol), tert-butyl 4-[(E)-3-(3,5- dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-but-l-enyl]-2-methyl-benzoate (0.4g, 0.88 mmol) and tris(2,4-ditert-butylphenyl) phosphite (0.1 equiv., 0.087 mmol) in toluene (8mL) in a stainless steel autoclave was purged three times with hydrogen (5 bar), pressurized at 25 bar with H2 followed by an additional 25 bar of CO (=50 bar CO/H2 1 : 1). The reaction was then heated at 100°C and vigorously stirred for 20h. The reaction was stopped by cooling the autoclave to room temperature, venting and purging with argon. The crude reaction was transferred into a 30 mL vial and 4-methylbenzenesulfonic acid (0.2 equiv., 0.173 mmol) was added and mixture was heated at reflux for 5 hours. The mixture was then cooled to room temperature, diluted with ethyl acetate and washed twice with NaHC03 sat aqueous solution, once with water and once with brine. The organic phase was then dried over magnesium sulfate, filtered and solvents were evaporated under reduced pressure. The crude product was purified over a silica gel column (eluent: cyclohexane / EtOAc) to yield a 154 mg of 4-[2-(3,5-dichlorophenyl)-2- (trifiuoromethyl)-3H-furan-4-yl]-2-methyl-benzoic acid. LCMS (Method A) RT 1.23 min; 1H-
NMR (CDC13, 400 MHz): 2.68(s, 3H), 3.35 (d, 1H), 3.78 (d, 1H), 7.10 (m, 2H), 7.18 (m, 1H), 7.42 (m, 1H), 7.52 (m, 2H), 8.10 (d, 1H). 19F-NMR (CDC13, 376.3 MHz):-79.4.
Step F: 4-[(2S)-2-(3 ,5 -dichlorophenyl)-2-(trifiuoromethyl)-3H-furan-4-yl]-N-( 1 , 1 -dioxothietan- 3-yl)-2-methyl-benzamide (compound D24*)
Figure imgf000305_0002
To a stirred solution of 4-[2-(3,5-dichlorophenyl)-2-(trifiuoromethyl)-3H-f
uran-4-yl]-2-methyl-benzoic acid (1 g, 2.40mmol) in dry dichloromethane (50mL) was added oxalyl chloride (1.0 equiv., 2.4 mmol) and then one drop of Ν,Ν-dimethylformamide. The reaction mixture was stirred at room temperature until no more CO formation was observed. The mixture was then evaporated to dryness and dissolved in dry dichloromethane (10 mL). This solution was then added dropwise at 0°C to a mixture of 1,1 -dioxothietan-3 -amine (1.1 equiv., 2.64mmol) and triethylamine in dry dichloromethane (20 mL). The mixture was stirred at 0°C for 30min and then allowed to stir at room temperature for 4 h and then quenched with water. The organic phase was washed once with brine and then solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography over a silica gel column (eluent: cyclohexane / EtOAc). After removal of the solvents, a colorless oil was obtained which was dissolved in a minimum of TBME and after dilution with heptanes a white precipitate appeared which was filtered and dried under high vacuum to yield the titled compound. Mp : 90- 105°C. LCMS (Method A) RT 1.16 min, [M+H]+ 567/569/571; 1H-NMR (CDC13, 400 MHz): 1- 55 (s, 2H), 2.45 (s, 3H), 3.29 (m, 1H), 3.72 (m, 1H), 4.01 (m, 2H), 4.61 (m, 2H), 4.87 (m, 1H), 6.45 (d, 1H), 7.01 (s, 1H), 7.10 (m, 2H), 7.26 (s, 1H), 7.37 (d, 1H), 7.41(m, 1H), 7.49(m, 2H). 19F-NMR (CDC13, 400 MHz): -80.87.
Chiral HPLC analysis:
Column: Daicel CHIRALPAK® IA, 3μιη, 0.46cm x 10cm
Mobile phase: Heptan/iPrOH/DEA 80/20 /0.1%
Flow rate: 1 ml/min
2 isomers were detected: rt= 8.88 min (84.4%) 10.79 min. (15.6 %).
Example P20: Preparation of 4-[(2S)-2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-furan-4-yll- 2 -methyl -N-r2-oxo-2-(2,2,2-trifluoroethylamino)ethyl1benzamide (compound D5 *
Figure imgf000306_0001
4-[(2S)-2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-furan-4-yl]-2-methyl-N-[2-oxo-2-(2,2,2- trifluoroethylamino)ethyl]benzamide was prepared using the protocol described for the preparation of compound D24*.
Mp : 120-155°C. LCMS (Methode A) RT 1.20 min; 1H-NMR (CDC13, 400 MHz): 2.48 (s, 3H), 3.32 (d, 2H), 3.75 (dd, 2H), 3.95 (m, 2H), 4.22 (d, 2H), 6.67 (t, 1H), 7.02 (s, 1H), 7.12 (m, 2H), 7.28 (s, 1H), 7.40 (m, 1H), 7.43 (m, 1H), 7.51 (m, 2H). 19F-NMR (CDC13, 376.3 MHz):-72.46. - 80.85. 3Q5
Chiral HPLC analysis:
Column: Daicel CHIRALPAK® IA, 3 μπι, 0.46cm x 10cm
Mobile phase: Heptan/EtOH 80/20
Flow rate: 1 ml/min
2 isomers were detected: rt= 5.56 min (84.2%) 8.14 min. (15.8%).
Example P21 : Preparation of enantioentriched tert-butyl 4-[3-(3,5-dichlorophenyl)-4,4,4- trifluoro-3 -hydroxy-but- 1 -ynyl] -2-methyl-benzoate
Figure imgf000307_0001
Step A: Preparation of 2-(3,5-dichlorophenyl)-l,l,l-trifluoro-but-3-yn-2-ol
Figure imgf000307_0002
In a 250 mL round bottom flask equipped with a reflux condenser, magnetic stirring and a thermometer under argon, was added bromo(ethynyl)magnesium (0.5M, 82.30 mmol). The solution was cooled to 0°C followed by dropwise addition of l-(3,5-dichlorophenyl)-2,2,2- trifluoro-ethanone (10 g, 41.1504 mmol) keeping the temperature under 7°C. The reaction was brought back to room temperature and was stirred overnight at room temperature. The reaction was cooled to 0°C and quenched carefully with HC1 (1M) until pH =1. The organic phase was then washed four times with water and once with brine. The combine organic phases were dried over MgS04, filtered and solvents were evaporated under reduced pressure. The crude product was distilled under reduced pressure (1 mBar, 120°C) to yield 9 g of a clear oil which solidified upon standing. 1H NMR (400 MHz, CDC13) 2.90 (s, 1H), 3.26 (s, OH), 7.45 (d, 1H), 7.55 (d, 2H); 19F-NMR (CDC13, 376.3 MHz):-80.40. Step B: Preparation of [l-(3,5-dichlorophenyl)-l-(trifluoromethyl)prop-2-ynyl] butanoate
Figure imgf000308_0001
In a 30 mL flask, 2-(3,5-dichlorophenyl)-l,l,l-trifluoro-but-3-yn-2-ol (2.69 g, 10 mmol) , triethylamine (1.31 g, 13 mmol) and N,N-dimethylpyridin-4-amine (0.061 g, 0.5 mmol) were dissolved in dichloromethane and cooled to 0°C. Then butanoyl chloride (1.39 g, 13 mmol) was added dropwise. The mixture was stirred overnight at room temperature. The mixture was taken up in MTBE and washed with HC1 (0.1 M), water, brine, dried over MgS04, filtered on a pad of silica gel and solvents were evaporated under reduced pressure to yield 3.5 g of a clear oil. 1H
NMR (400 MHz, CDC13) 1.05 (m, 3H), 1.72 (m, 2H), 2.48 (m, 2H), 3.00 (s, 1H), 7.43 (d, 1H), 7.52 (d, 2H); 19F-NMR (CDC13, 376.3 MHz):-78.40.
Step C: Preparation of [(lS)-l-(3,5-dichlorophenyl)-l-(trifluoromethyl)prop-2-ynyl] butanoate and (2Pv)-2-(3,5-dichlorophenyl)- 1,1,1 -trifluoro-but-3-yn-2-ol
Figure imgf000308_0002
A solution of Lipase from Candida rugosa (5 g) in phosphate buffer pH = 7.4, 100 mM (100 mL) was mechanically stirred in a 250 mL glass reactor (500 rpm) at room temperature for 2 hours. Then a solution of [l-(3,5-dichlorophenyl)-l-(trifluoromethyl)prop-2-ynyl] butanoate (10 g) in DMSO (20 mL) was added to the previous solution. The reaction mixture was mechanically stirred at 55°C (internal temperature), 500 rpm for 2 days. Aliquots were analyzed by LCMS during the course of the experiment. After 50 h, 1.742 g of K2HP04 (10 mmol) was added to the mixture and stirred for a further 20 h. At this point Celite (20 g) was added and the reaction was filtered through on a Celite plug. The Celite cake was then rinsed with ethyl acetate (7x100 mL). The clear biphasic mixture was decanted and the aqueous phase was extracted with ethyl acetate (2x100 mL). The gathered organic phases were washed with brine (100 mL), dried on MgS04, and concentrated under vacuum (40°C, 30 mbar). A viscous orange oil (m = 10.80 g) was obtained. The crude product was purified by flash chromatography over a silica gel column (eluent: cyclohexane / EtOAc) to yield 4.85 g of [(lS)-l-(3,5-dichlorophenyl)-l- (trifluoromethyl)prop-2-ynyl] butanoate and 2.93 g of (2R)-2-(3,5-dichlorophenyl)-l,l,l- trifluoro-but-3-yn-2-ol.
A solution of [(lS)-l-(3,5-dichlorophenyl)-l-(trifluoromethyl)prop-2-ynyl] butanoate (108 mg in 10 mL CHC13) in such manner was analyzed for optical rotation at 20°C. This [CX]D at 20°C was -15.37°. The use of (S)-(+)-l-(9-Anthryl)-2,2,2-trifluoroethanol enabled to determine an ee=56
%.
A solution of this (2R)-2-(3,5-dichlorophenyl)-l,l,l-trifluoro-but-3-yn-2-ol (57 mg in 5 mL CHC13) in such manner was analysed for optical rotation at 20°C. This [α]ο at 20°C was +7.28°. Chiral GC analysis:
GC was conducted on a Thermo Focus GC, with a column from Supelco Alpha DEX 120 fused silica Capillary Column: 30m, diam: 0.25 mm, 0.25 μιη, H2 flow 1. ml/min, temp injector:
220°C, FID Detector: temp detector: 300°C, method: start at 80 °C, hold 2min, 5,5°C/min until 220°C, hold 3 min, total time 30min
2 isomers were detected: rt= 23.37 min (86.0%) 24.32 min. (14.0 %).
Step C : Alternative preparation of enantioenriched 2-(3,5-dichlorophenyl)-l,l,l-trifluoro-but-3- y -2-ol
Figure imgf000309_0001
A solution of /? -butyl lithium (1.27 mL, 3.29 mmol) in hexanes (2.6M) was added to a solution of trimethylsilylacetylene (162 mg, 1.65 mmol) and (lR,2S)-l-phenyl-2-pyrrolidin-l-yl-propan-l- ol (338 mg, 1.65 mmol) in dry THF (2 mL) slowly at -10°C. The resulting solution was stirred for 30 minutes at 0°C under argon. A solution of l-(3,5-dichlorophenyl)-2,2,2-trifluoro-ethanone (200 mg, 0.82 mmol) in THF (2mL) was added slowly at -40°C and stirred at the same temperature for additional 30 minutes. After addition of HCl (1M), the reaction mixture was extracted by diethyl ether. The organic phase was dried (Na2S04) and evaporated giving colorless oil (327 mg). The oily residue was solubilized in ethanol (5mL) and treated with potassium carbonate (341 mg, 2.47 mmol) for 2h at RT. Potassium carbonate was filtered off and the title compound was isolated by column chromatography (eluent cyclohexane / EtOAc) as a - 30ο - colorless liquid in 88 mg (40%) yield. Ή NMR (400 MHz, CDC13) 2.90 (s, 1H), 3.26 (s, OH),
7.45 (d, 1H), 7.55 (d, 2H); 19F-NMR (CDC13, 376.3 MHz):-80.40.
Chiral GC analysis:
GC was conducted on a Thermo Focus GC, with a column from Supelco Alpha DEX 120 fused silica Capillary Column: 30m, diam: 0.25 mm, 0.25 μιη, ¾ flow 1. ml/min, temp injector:
220°C, FID Detector: temp detector: 300°C, method: start at 80 °C, hold 2min, 5,5°C/min until 220°C, hold 3 min, total time 30min
2 isomers were detected: rt= 23.37 min (15.0 %) 24.32 min. (85.0%).
Step D Preparation of tert-butyl 4-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-but-l- ynyl]-2 -methyl -benzoate
Figure imgf000310_0001
To a solution of tert-butyl 4-bromo-2-methyl-benzoate (1.1 mmol, 0.298g) in N,N- dimethylformamide is added successively at room temperature diisopropylamine (20 equiv., 20 mmol, 2.83ml), cooper-(I)-iodide (0.4 mmol, 78mg) and dichlorobis
(triphenylphosphine)palladate(II) (0.4 mmol, 281mg). Argon was bubbled through the reaction for 5 minutes after which the enriched (2R)-2-(3,5-dichlorophenyl)-l,l,l-trifiuoro-but-3-yn-2-ol (1.1 mmol, 0.296 g, obtained as described in step C) was added in 1ml of DMF. The black mixture is heated under argon at 80°C for 2hl5. The reaction mixture is filtered through celite and washed with EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organic phases is washed 3 times with saturated NaCl solution. The organic phase was then dried over sodium sulfate and the solvents after filtration were evaporated under reduced pressure and filtered on a pad of silica gel to yield 40 mg of a clear oil. LCMS (method A) RT 1.37 min; 1H-NMR (CDC13, 400 MHz): 1.49 (s, 9H), 2.04 (s, 3H), 3.70 (s, 1H, OH), 7.18 (m, 1H), 77.22 (m, 1H), 7.30 (m, 1H), 7.54 (m, 2H), 7.65 (d, 1H). 19F-NMR (CDC13, 376.3 MHz):- 80.05.
Chiral HPLC analysis:
Column: Daicel CHIRALPAK® IB, 3μιη, 0.46cm x
Mobile phase: Hept/DCM 50/50 Flow rate: 1.0 ml/min
2 isomers were detected: rt= (22.0%) 2.28 min. (78.0%).
Example P21 : Preparation of 5-[(2S)-2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-furan-4-yl]- 5 2- 1 ,2,4-triazol- 1 -yl)benzonitrile (compound HI *)
Figure imgf000311_0001
Ste A: Preparation of 5-iodo-2-(l,2,4-triazol-l-yl)benzonitrile
Figure imgf000311_0002
To a solution of 2-fluoro-5-iodo-benzonitrile (25.3 g) and 1H-1,2,4-TRIAZ0LE (8.66 g) in N,N- 10 dimethylformamide (102 mL) was added cesium carbonate (40.0 g) and the mixture was heated at 60°C for 5 hours. The beige-brown suspension was cooled to room temperature and allowed to stand for 6 days. The mixture was dissolved in ethyl acetate, washed with a hydrochloric solution (1M). The combined organic layers were dried over magnesium sulfate, filtered and evaporated to obtain the desired product as a white solid (28g). 1H NMR (CDC13, 400MHz): δ = 8.79 (s, 1
15 H), 8.20 (s, 1 H), 8.16 (d, J=1.8 Hz, 1 H), 8.04 - 8.12 (m, 1 H), 7.55 ppm (d, J=8.4 Hz, 1 H) Step B: Preparation of (2S)-2-(3,5-dichlorophenyl)-l,l,l-trifluoro-but-3-yn-2-ol
Figure imgf000311_0003
To a solution of [(lS)-l-(3,5-dichlorophenyl)-l-(trifluoromethyl)prop-2-ynyl] butanoate 20 (obtained as described in the preparative example P20 step C) (4.60 g) dissolved in
dimethylsulfoxide (15 mL) was added sodium hydroxide 0.25M (220 mL) at room temperature. The mixture was stirred at room temperature for 17 hours then was heated to 60°C for another 6.5 hours. Then more sodium hydroxide 2.0 M (13.6 mL) was added and the mixture was stirred at 60°C for 16 hours. More sodium hydroxide (2.21 g) was added and the mixture was stirred at 25 60°C for 5 hours. The solution was then cooled to 15°C and acidified with HC1 37% to reach pH=3. The mixture was dissolved in diethylether, washed with water. The combined organic layers were dried over magnesium sulfate, filtered and evaporated to obtain a crude residue that was further dissolved in diethylether and washed with a sodium carbonate solution (1M). The combined organic layers were dried over magnesium sulfate, filtered and evaporated to obtain a bright yellow oil (3.60 g) as the titled compound. 1H NMR (400 MHz, CDC13) 2.90 (s, 1H), 3.26 5 (s, OH), 7.45 (d, 1H), 7.55 (d, 2H); 19F-NMR (CDC13, 376.3 MHz):-80.40.
Chiral GC analysis:
GC was conducted on a Thermo Focus GC, with a column from Supelco Alpha DEX 120 fused silica Capillary Column: 30m, diam: 0.25 mm, 0.25 μιη, H2 flow 1. ml/min, temp injector: 10 220°C, FID Detector: temp detector: 300°C, method: start at 80 °C, hold 2min, 5,5°C/min until 220°C, hold 3 min, total time 30min
2 isomers were detected: rt= 23.37 min (29 %) 24.32 min. (71%).
Step C: Preparation of 5-[(3R)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-but-l-ynyl]-2- 15 (1 ,2,4-triazol- 1 -yl)benzonitrile
Figure imgf000312_0001
To a solution of [(lS)-l-(3,5-dichlorophenyl)-l-(trifluoromethyl)prop-2-ynyl] butanoate (4.0 g, 15 mmol) and 5-iodo-2-(l,2,4-triazol-l-yl)benzonitrile (4.4 g, 15 mmol) in N,N- dimethylformamide (36 mL) is added successively at room temperature triethylamine (30 g, 41
20 mL, 300 mmol ), cooper-(I)-iodide (1.1 g, 5.9 mmol) and
dichlorobis(triphenylphosphine)palladate(II) (1.1 g, 1.5 mmol) under argon. The mixture was heated to 80°C for 3 hours then the mixture was dissolved in ethyl acetate. The suspension was washed with a hydrochloric solution (1M) to reach ph=4. The combined organic layers were dried over magnesium sulfate, filtered and evaporated to give a residue that was suspended in
25 dichloromethane. The suspension was filtered and the solid was washed with dichloromethane then dried under vacuo to give the titled compound as beige solid (1.25g).
The mother liquors were further concentrated under vacuo and purified using a silica gel column (eluent: cyclohexane / EtOAc) giving the titled compound as pale brown solid (2.92 g). 1H
NMR (DMSO d6, 400MHz): δ = 9.31 (br. s., 1 H), 8.56 (s, 1 H), 8.43 (d, J=1.8 Hz, 2 H), 8.12 30 (dd, J=8.4, 1.8 Hz, 1 H), 7.99 (d, J=8.8 Hz, 1 H), 7.80 (t, J=l .8 Hz, 1 H), 7.68 - 7.77 ppm (m, 2 H) 1 1
Step D: Preparation of 5-[(E,3S)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-but-l-enyl]-2- ( 1 ,2,4-triazol- 1 -yl)benzonitrile
Figure imgf000313_0001
To a solution of 5-[(3R)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-but-l-ynyl]-2-(l,2,4- triazol-l-yl)benzonitrile (3.12 g) in 15.7 mL of toluene and 5.71 mL of THF cooled to -30°C, sodium bis (2-methoxyethoxy)aluminum hydride (65 mass% in Toluene) (2.56 mL) was added. The reaction was stirred at -30°C for 3 h. The reaction mixture was carefully quenched first with acetone at -30°C and then with NH4C1 solution sat at -10°C and extracted twice with ethyl acetate. The combined organic layers were dried (MgS04), filtered and evaporated to give a yellow residue that was suspended in dichloromethane. The suspension was filtered and the solid was washed with dichloromethane then dried under vacuo to give the titled compound as yellow solid (1.49g). The mother liquors were further concentrated under vacuo and purified using a silica gel column (eluent: cyclohexane / EtOAc) giving the titled compound (791 mg). 1H-NMR (DMSO d6, 400 MHz): δ = 9.21 (s, 1 H), 8.49 (d, J=1.8 Hz, 1 H), 8.37 (s, 1 H), 8.14 (dd, J=8.6, 2.0 Hz, 1 H), 7.89 (d, J=8.4 Hz, 1 H), 7.80 (d, J=1.8 Hz, 2 H), 7.71 (t, J=1.8 Hz, 1 H), 7.60 (s, 1 H), 7.41 (d, J=15.8 Hz, 1 H), 7.05 ppm (d, J=16.1 Hz, 1 H)
Step E: 5-r(2S -2-(3,5-dichlorophenvn-2-(trifiuoromethvn-3H-furan-4-vll-2-(l,2,4-triazol-l- yl)benzonitrile (compound HI *)
Figure imgf000313_0002
A homogeneous solution of [Rh(CO)2acac] (0.0135 g), tris(2,4-ditert-butylphenyl) phosphite (0.336 g) and 5-[(E,3S)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxy-but-l-enyl]-2-(l,2,4- triazol-l-yl)benzonitrile (2.28 g) in tetrahydrofuran (20 mL) in a stainless steel autoclave was purged three times with hydrogen (5 bar), pressurized at 25 bar with H2 followed by an additional 25 bar of CO (=50 bar CO/H2 1 : 1). The reaction was then heated at 100°C and vigorously stirred for 70h. The reaction was stopped by cooling the autoclave to room
temperature, venting and purging with argon. The mixture was dissolved in ethyl acetate, washed with water. The combined organic layers were dried over magnesium sulfate, filtered and evaporated to obtain a crude residue which was purified using a silica gel column (eluent:
cyclohexane / EtOAc) giving the hydro fomylated compound (2.14 g) as a beige foam that was used as such (mixture of diastereoisomers) in the next step.
The residue (2.47 g) was dissolved in xylenes (98 mL) and 4-methylbenzenesulfonic acid (1.10 g) was added. The mixture was heated to 120°C for 15.5 hours. The mixture was then cooled to room temperature, and slowly poured on a cold saturated sodium carbonate solution. The 5 mixture was diluted with ethyl acetate and washed twice with a saturated solution of sodium hydrogenocarbonate. The combined organic layers were dried over magnesium sulfate, filtered and evaporated to obtain a crude residue which was purified using a silica gel column (eluent: cyclohexane / EtOAc containing 1% NEt3) to provide the titled compound (1.59 g) as a beige foam.
10 1H-NMR (CDC13, 400 MHz): δ = 8.76 (s, 1 H), 8.19 (s, 1 H), 7.68 - 7.78 (m, 1 H), 7.56 - 7.67 (m, 2 H), 7.49 (d, J=1.5 Hz, 2 H), 7.40 - 7.47 (m, 1 H), 7.13 (s, 1 H), 3.78 (dd, J=15.2, 2.0 Hz, 1 H), 3.36 ppm (d, J=15.4 Hz, 1 H)
Chiral HPLC analysis:
15 Column: Daicel CHIRALPAK® IA, 3μιη, 0.46cm x 10cm
Mobile phase: Heptan/iPrOH/DEA 70/30 /0.1%
Flow rate: 1 ml/min
2 isomers were detected: rt= 3.82 min (71.4%) 5.30 min. (28.6 %). LC/MS Method A
MS ACQUITY SQD Mass Spectrometer from Waters (Single quadrupole mass spectrometer)
Ionisation method: Electrospray
Polarity: positive ions
Capillary (kV) 3.00, Cone (V) 20.00, Extractor (V) 3.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 400, Cone Gas Flow (L/Hr) 60, Desolvation Gas Flow
(L/Hr) 700
Mass range: 100 to 800 Da
DAD Wavelength range (nm): 210 to 400
LC Method Waters ACQUITY UPLC with the following HPLC gradient conditions
(Solvent A: Water/Methanol 9: 1,0.1% formic acid and Solvent B: Acetonitrile,0.1% formic acid )
Time (minutes) A B Flow rate (ml/min)
0 100 0 0.75
2.5 0 100 0.75
2.8 0 100 0.75
3.0 100 0 0.75
Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron; Temperature: 60°C.
MC/MS : Method B
MS ZQ Mass Spectrometer from Waters (single quadrupole mass spectrometer), ionization
method: electrospray, polarity: negative ionization, capillary (kV) 3.00, cone (V) 45.00, source temperature (°C) 100, desolvation temperature (°C) 250, cone gas flow (L/Hr) 50, desolvation gas flow (L/Hr) 400, mass range: 150 to 1000 Da.
LC HP 1100 HPLC from Agilent: solvent degasser, binary pump, heated column compartment and diode-array detector.
Column: Phenomenex Gemini CI 8, length (mm) 30, internal diameter (mm) 3, particle size (μιη) 3, temperature (°C) 60, DAD wavelength range (nm): 200 to 500, solvent gradient: A = 0.05% v/v formic acid in water and B = 0.04%> v/v formic acid in acetonitrile / methanol
(4: 1).
Time (min) A% B% Flow (ml/min)
0.0 95 5.0 1.7
2.0 0.0 100 1.7
2.8 0.0 100 1.7
2.9 95 5.0 1.7
3.1 95 5 1.7
Table A
Figure imgf000315_0001
Comp R1 R2 RT (min) MH+ Method No.
A18 H (lH-Benzoimidazol-2-yl)-methyl 1.66 546 A
A19 H 3 -Bromo -propyl 2.07 536 A
A20 H 3 ,3 ,3 -Trifluoro-propyl 2.09 512 A
A21 H Dihydro-thiophen-2-one-3 -yl 2.01 516 A
A22 H 6-Ethoxycarbonyl-cyclohex-3-enyl 2.24 568 A
A23 H 2-Benzo[l ,3]dioxol-5-yl-ethyl 2.14 564 A
A24 H 2-Benzylsulfanyl-ethyl 2.26 566 A
A25 H 4-Methanesulfonyl-benzyl 1.95 584 A
A26 H Ν',Ν'-Dimethylamino -ethyl 1.49 487 A
A27 H sec-Butyl 2.13 472 A
A28 H Butan-l-ol-2-yl 1.90 488 A
A29 H 2,2-Difluoro-ethyl 2.01 480 A
A30 H 1 -Ethynyl-cyclohexyl 2.26 522 A
A31 H 2-[l,3]Dioxolan-2-yl-ethyl 1.97 516 A
A32 H 2-Methyl-cyclohexyl 2.29 512 A
A33 H 2-Morpholin-4-yl-ethyl 1.44 529 A
A34 H 3 -Pyrrolidin- 1 -yl -propyl 1.47 527 A
A35 H (Pyrid-3-yl)-methyl 1.67 507 A
A36 H 3 -Piperidin- 1 -yl -propyl 1.50 541 A
[3 -(4-Chloro-phenyl)-isoxazol-5-yl] -
607
A37 H methyl 2.27 A
A38 H 1 -Phenyl-ethyl 2.19 520 A
A39 H Phenethyl 2.19 520 A
A40 H l,2,2,6,6-Pentamethyl-piperidin-4-yl 1.54 569 A
A41 H 2-Thiophen-2-yl-ethyl 2.17 526 A
A42 H 2-Phenoxy-ethyl 2.18 536 A
A43 H 3-Chloro-benzyl 2.23 540 A
(2,3-Dihydro-benzo[l,4]dioxin-6-yl)-
A44 H 2.10 564 A methyl
A45 H 2-Acetylamino-ethyl 1.77 501 A
A46 H 4-Pyrazol-l -yl -benzyl 2.10 572 A
A47 H 2-(lH-Indol-3-yl)-ethyl 2.12 559 A
A48 H 2-Trifluoromethyl-benzyl 2.26 574 A
A49 H 2-Methylsulfanyl-ethyl 2.06 490 A Comp R1 R2 RT (min) MH+ Method No.
A50 H 2-Piperidin-l -yl -benzyl 1.95 589 A
A51 H 4-Phenoxy-benzyl 2.33 598 A
A52 H (6-Chloro-pyridin-3-yl)-methyl 2.06 541 A
A53 H 1 -Benzyl-pyrrolidin-3-yl 1.62 575 A
A54 H 2-(4-Benzyl-piperazin-l -yl)-ethyl 1.61 618 A
A55 H Furan-2-yl-methyl 2.06 496 A
A56 H 2-Chloro-phenyl 2.32 526 A
A57 H Quinolin-5-yl 1.95 543 A
A58 H 2,4-Dimethoxy-phenyl 2.24 552 A
A59 H 3 -Fluorophenyl 2.23 510 A
A60 H lH-Indazol-5-yl 1.96 532 A
A61 H 4-Pyrrol- 1 -yl -phenyl 2.29 557 A
A62 H 4-Piperidin-l -yl -phenyl 1.86 575 A
A63 H 2-Methylsulfanyl-phenyl 2.33 538 A
A64 H Benzothiazol-6-yl 2.13 549 A
A65 H 4-Methyl-2-oxo-2H-chromen-7-yl 2.16 574 A
A66 H 4-Dimethylsulfamoyl-phenyl 2.14 599 A
A67 H 2,5-Dimethyl-2H-pyrazol-3-yl 1.98 510 A
A68 H 5-Methylsulfanyl-lH-[l,2,4]triazol-3-yl 2.15 529 A
A69 H 4-Hydroxy-6-methyl-pyrimidin-2-yl 1.94 524 A
A70 H Quinolin-2-yl 2.30 543 A
A71 H 5-Methyl-3-phenyl-isoxazol-4-yl 2.17 573 A
A72 H 9H-Purin-6-yl 1.84 534 A
A73 H 5-Acetyl-4-methyl-thiazol-2-yl 2.17 555 A
A74 H 4-Methyl-benzothiazol-2-yl 2.42 563 A
A75 H 5-Methyl-[l,3,4]thiadiazol-2-yl 2.05 514 A
4,6-Dimethyl-2H-pyrazolo[3,4-b]pyridin-
A76 H 1.98 561 A
3-yl
All H 1 -Oxo-thietan-3 -yl 1.78 504 A
A78 H Thietan-3 -yl -methyl 2.07 502 A
3-(2,2,2-Trifluoro-ethoxyimino)-
581
A79 H cyclobutyl 2.14 A
A80 H Thietan-2-yl-methyl 2.09 502 A
A81 H (1,1 -Dioxo-thietan-2-yl)-methyl 1.88 534 A Comp R1 R2 RT (min) MH+ Method No.
A82 H 2-Thietan-3 -yl-ethyl 2.12 516 A
A83 H 2-(l , 1 -Dioxo-thietan-3-yl)-ethyl 1.87 548 A
3-Oxo-2-(2,2,2-trifluoro-ethyl)-
A84 H 2.03 583 A isoxazolidin-4-yl
A85 H H See NMR See NMR See NMR
A86 H See NMR See NMR See NMR
H
Table B
Figure imgf000318_0001
Comp R R2 RT (min) MH+ Method No.
Bl H 2,2,2-Trifluoro-ethyl 1.99 485 A
B2 H Ethyl 1.87 431 A
B3 H n-Butyl 2.05 459 A
B4 H 2-Methoxy- 1 -methyl-ethyl 1.91 475 A
B5 H (2,2,2-Trifluoro-ethylcarbamoyl)-methyl 1.82 542 A
B6 H 3 ,3 ,3 -Trifluoro-propyl 2.00 499 A
B7 H sec-Butyl 2.03 459 A
B8 H (Tetrahydro -furan-2 -yl) -methyl 1.89 487 A
B9 H Benzyl 2.06 493 A
BIO H 2-Fluoro-benzyl 2.07 511 A
Bl l H 1 -Phenyl-ethyl 2.10 507 A
B12 H 4-Methoxy-benzyl 2.04 523 A
B13 H 1 , 1 -Dioxo-thietan-3 -yl 1.77 507 A
B14 H (6-Chloro-pyrid-3 -yl) -methyl 1.96 528 A
B15 H 3-Fluoro-phenyl 2.15 497 A
B16 H (Pyrid-2-yl)-methyl 1.72 494 A
B17 H 2,5-Dimethyl-2H-pyrazol-3-yl 1.87 497 A
B18 H 4-Methyl-thiazol-2-yl 2.07 500 A Comp R1 R2 RT (min) MH+ Method No.
B19 H 3 -Methyl-thietan-3 -yl 2.05 489 A
B20 H 1 , 1 -Dimethyl-2-methylsulfanyl-ethyl 2.14 505 A
B21 H Thietan-3-yl 1.96 475 A
B22 H Bicyclo[2.2.1]hept-2-yl 2.17 497 A
B23 H Cyclobutyl 2.00 457 A
B24 H 1 -Oxo-thietan-3 -yl 1.69 491 A
Table C
Figure imgf000319_0001
Comp R R2 RT (min) MH+ Method No.
CI H 2,2,2-Trifluoro-ethyl 2.07 499 A
C2 H Ethyl 1.94 445 A
C3 H n-Butyl 2.12 473 A
C4 H 2-Methoxy- 1 -methyl-ethyl 1.99 489 A
C5 H (2,2,2-Trifluoro-ethylcarbamoyl)-methyl 1.90 556 A
C6 H 3 ,3 ,3 -Trifluoro-propyl 2.07 513 A
C7 H sec-Butyl 2.10 473 A
C8 H (Tetrahydro -furan-2 -yl) -methyl 1.97 501 A
C9 H Benzyl 2.13 507 A
CIO H 2-Fluoro-benzyl 2.14 525 A
Cl l H 1 -Phenyl-ethyl 2.17 521 A
C12 H 4-Methoxy-benzyl 2.10 537 A
C13 H 1 , 1 -Dioxo-thietan-3 -yl 1.85 521 A
C14 H (6-Chloro-pyrid-3 -yl) -methyl 2.04 542 A
C15 H 3-Fluoro-phenyl 2.22 511 A
C16 H 2,5-Dimethyl-2H-pyrazol-3-yl 1.96 511 A
C17 H 3 -Methyl-thietan-3 -yl 2.12 503 A
C18 H 1 , 1 -Dimethyl-2-methylsulfanyl-ethyl 2.21 519 A
C19 H Thietan-3-yl 2.03 489 A Comp R1 R2 RT (min) MH+ Method No.
C20 H Bicyclo[2.2.1]hept-2-yl 2.23 511 A
C21 H Cyclobutyl 2.06 471 A
C22 H 1 -Oxo-thietan-3 -yl 1.76 505 A
Table D
Figure imgf000320_0001
Comp R R2 RT (min) MH+ Method No.
Dl H 2,2,2-Trifluoro-ethyl 2.10 498 A
D2 H Ethyl 1.99 444 A
D3 H n-Butyl 2.16 472 A
D4 H 2-Methoxy- 1 -methyl-ethyl 2.04 488 A
D5 H (2,2,2-Trifluoro-ethylcarbamoyl)-methyl 1.95 555 A
D6 H 3 ,3 ,3 -Trifluoro-propyl 2.10 512 A
D7 H sec-Butyl 2.15 472 A
D8 H (Tetrahydro -furan-2 -yl) -methyl 2.02 500 A
D9 H Benzyl 2.16 506 A
D10 H 2-Fluoro-benzyl 2.17 524 A
Dl l H 1 -Phenyl-ethyl 2.21 520 A
D12 H 4-Methoxy-benzyl 2.14 536 A
D13 H (6-Chloro-pyrid-3 -yl) -methyl 2.07 541 A
D14 H 3-Fluoro-phenyl 2.29 510 A
D15 H (Pyrid-2-yl)-methyl 1.85 507 A
D16 H 2,5-Dimethyl-2H-pyrazol-3-yl 1.99 510 A
D17 H 4-Methyl-thiazol-2-yl 2.19 513 A
D18 H 3 -Methyl-thietan-3 -yl 2.16 502 A
D19 H 1 , 1 -Dimethyl-2-methylsulfanyl-ethyl 2.27 518 A
D20 H 1 -Oxo-thietan-3 -yl 1.80 504 A
D21 H Thietan-3-yl 2.07 488 A
D22 H Bicyclo[2.2.1]hept-2-yl 2.29 510 A Comp R1 R2 RT (min) MH+ Method No.
D23 H Cyclobutyl 2.11 470 A
D24 H 1 , 1 -Dioxo-thietan-3 -yl 1.90 520 A
Table E
Figure imgf000321_0001
Comp R R2 RT (min) MH+ Method No.
El H 2,2,2-Trifluoro-ethyl 2.01 512 A
E2 H Ethyl 1.91 458 A
E3 H n-Butyl 2.07 486 A
E4 H 2-Methoxy- 1 -methyl-ethyl 1.96 502 A
E5 H (2,2,2-Trifluoro-ethylcarbamoyl)-methyl 1.88 569 A
E6 H 3 ,3 ,3 -Trifluoro-propyl 2.03 526 A
E7 H (Tetrahydro -furan-2 -yl) -methyl 1.93 514 A
E8 H Benzyl 2.10 520 A
E9 H 2-Fluoro-benzyl 2.11 538 A
E10 H 1 -Phenyl-ethyl 2.15 534 A
El l H 4-Methoxy-benzyl 2.06 550 A
E12 H (6-Chloro-pyrid-3-yl)-methyl 2.00 555 A
E13 H (Pyrid-2-yl)-methyl 1.78 521 A
E14 H 2,5-Dimethyl-2H-pyrazol-3-yl 1.92 524 A
E15 H 4-Methyl-thiazol-2-yl 2.10 527 A
E16 H 3 -Methyl-thietan-3 -yl 2.10 516 A
E17 H Thietan-3-yl 2.02 502 A
E18 H Cyclobutyl 2.04 484 A
E19 H 1 -Oxo-thietan-3 -yl 1.73 518 A „„Λ
Table F
Figure imgf000322_0001
Figure imgf000322_0003
Table G
Figure imgf000322_0002
Figure imgf000322_0004
The enantioenriched compounds can be obtained by chiral separation on preparative HPLC, which was conducted on compound D24 according to the following procedure:
Analytical HPLC method:
HPLC from Waters: allianceHT, 996 Waters UV/Visible Detector, 2795 Separation Module
Column: Daicel CHIRALPAK® IA-3, 0.46cm x 10cm
Mobile phase: Heptan/2-Propanol/0.1DEA 70/30
Flow rate: 1 ml/min
Detection: UV 270 nm
Temperature: 25°C
Preparative HPLC method:
Autopurification System from Waters: 2767 sample Manager, 2489 UV/Visible Detector, 2545 Quaternary Gradient Module.
Column: Daicel CHIRALPAK® IA l.O cm x 25cm
Mobile phase: Heptan/2-Propanol/0.1DEA 70/30 Flow rate: 5 ml/min
Detection: UV 270 nm
Temperature: 25°C
Results:
From 101 mg crude material, 2 compounds could be isolated:
Figure imgf000323_0001
Biological examples of racemic mixtures
Spodoptera Uttoralis (systemic) (Egyptian cotton leaf worm)
Test compounds were applied by pipette into 24 well plates and mixed with agar. Salad seeds were placed on the agar and the multi well plate is closed by another plate which contains also agar. After 7 days the roots have absorbed the compound and the salad has grown into the lid plate. The salad leafs were now cut off into the lid plate. Spodoptera eggs were pipette through a plastic stencil on a humid gel blotting paper and the plate closed with it. The samples are checked for mortality, repellent effect, feeding behavior, and growth regulation 5 days after infestation. Application rate: 12.5ppm
The following compound gave at least 80% control of Spodoptera Uttoralis: Al, A2, A13, A15, A16, C5, C13, A77, D24, Fl, Dl, D24, D5, D8, D15, D20, D21.
Spodoptera Uttoralis (Egyptian cotton leafworm):
Cotton leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs were infested with 5 LI larvae. The samples were checked for mortality, feeding behavior, and growth regulation 3 days after treatment (DAT).
The following compound gave at least 80%> control of Spodoptera Uttoralis: Al, A2, A3, A4, A5, A6, A7, A8, A9, A10, Al 1, A12, A13, A14, A15, A16, CI, C2, C3, C4, C5, C6, C7, C8, C9, CIO, CI 1, C12, C13, C14, C15, C17, C18, C19, C20, C21, C22, A86, Gl, G2, A17, A19, A20, A21, A25, A26, A27, A28, A29, A31, A35, A38, A42, A43, A44, A49, A52, A53, A55, A57, A59, A60, A64, A67, A72, A77, A78, A79, A80, A81, A82, A83, A84, D24, Fl, Dl, D24, D3, D4, D5, D5*, D6, D7, D8, D9, D10, Dl 1, D12, D13, D14, D15, D16, D17, D18, D19, D20, D21, D23, F2, E5, E6, E8, E13, E15, E19, D24, D25
Heliothis virescens (Tobacco budworm):
Eggs (0-24 h old) were placed in 24-well microtiter plate on artificial diet and treated with test solutions at an application rate of 200 ppm (concentration in well 18 ppm) by pipetting. After an incubation period of 4 days, samples were checked for egg mortality, larval mortality, and growth regulation. ^2
The following compound gave at least 80% control of Heliothis virescens: Al, A2, A3, A4, A5, A6, A7, A8, A9, A10, Al l, A12, A13, A14, A15, A16, B5, B14, CI, C3, C5, C7, C8, C9, CIO, Cl l, C12, C13, C14, C15, C16, C20, C21, C22, A86, Gl, A17, A18, A19, A20, A21, A25, A27, A29, A35, A38, A39, A42, A44, A46, A49, A52, A54, A55, A56, A57, A58, A59, A60, A64, A66, A67, A69, A77, A78, A79, 5 A80, A81, A82, A83, A84, D24, Fl, Dl, D24, D3, D4, D5, D5*, D6, D7, D8, D9, D10, Dl 1, D12, D13, D14, D15, D16, D17, D18, D19, D20, D21, D23, F2, E5, D24, D25, HI *.
Plutella xylostella (Diamond back moth):
24-well microtiter plate (MTP) with artificial diet was treated with test solutions at an application rate of 10 200 ppm (concentration in well 18 ppm) by pipetting. After drying, the MTPs were infested with L2 larvae (7-12 per well). After an incubation period of 6 days, samples were checked for larval mortality and growth regulation.
The following compound gave at least 80% control of Plutella xylostella: Al, A2, A3, A4, A5, A6, A7, A8, A9, A10, Al 1, A12, A13, A14, A15, A16, Bl, B7, B8, B9, B23, CI, C2, C3, C5, C6, C7, C9, CIO, 15 Cl l, C12, C13, C14, C15, C16, C17, C19, C20, C21, C22, A86, Gl, A17, A18, A19, A20, A21, A25, A27, A29, A30, A31, A32, A35, A38, A39, A41, A44, A46, A49, A52, A55, A56, A57, A58, A59, A60, A63, A64, A67, A69, A77, A78, A79, A80, A81, A82, A83, A84, D24, Fl, Dl, D24, D3, D4, D5, D6, D7, D8, D9, D10, Dl l, D12, D13, D5*, D14, D15, D16, D17, D18, D19, D20, D21, D22, D23, F2, E3, E5, E6, E9, El l, E13, D24, D25, HI *.
20
Diabrotica balteata (Corn root worm):
A 24-well microtiter plate (MTP) with artificial diet was treated with test solutions at an application rate of 200 ppm (concentration in well 18 ppm) by pipetting. After drying, the MTPs were infested with L2 larvae (6-10 per well). After an incubation period of 5 days, samples were checked for larval mortality
25 and growth regulation.
The following compound gave at least 80%> control of Diabrotica balteata: Al, A2, A3, A4, A5, A6, A7, A8, A9, A10, Al 1, A12, A13, A14, A15, A16, B2, B6, B12, B19, CI, C2, C3, C5, C6, C7, C8, C9, CIO, Cl l, C12, C13, C14, C17, C18, C19, C20, C21, C22, A86, Gl, A17, A18, A19, A20, A21, A25, A27, A29, A30, A31, A32, A35, A38, A39, A41, A42, A43, A44, A46, A48, A49, A50, A52, A53, A54, A55,
30 A56, A57, A58, A59, A60, A61, A63, A64, A65, A66, A67, A69, A75, A77, A78, A79, A80, A81, A82, A83, A84, D24, Fl, Dl, D24, D3, D4, D5, D5*, D6, D7, D8, D9, D10, Dl l, D12, D13, D14, D15, D16, D17, D18, D19, D20, D21, D22, D23, E5, E13, E15, E17, D24, D25, HI *.
Myzus persicae (sachet) (Green peach aphid) mixed population
35 Test compounds were applied by pipette into 24 well plates and mixed with Sucrose solution. The plates were closed with a stretched Parafilm. A plastic stencil with 24 holes is placed onto the plate and infested pea seedlings were placed directly on the Parafilm. The infested plate is closed with a gel blotting paper and another plastic stencil and then turned upside down. 5 days after infestation the samples were checked on mortality. Application rate: 12.5ppm.
The following compounds gave at least 80% control of Myzus persicae: Al, A2, A8, A13, A15, A16, C5, C13, C22, A25, A77, A78, A82, A83, A84, D24, Fl, D24, D3, D4, D5, D5*, D6, D7, D8, D9, D10, Dl 1, D12, D13, D14, D15, D16, D17, D18, D19, D20, D21, D23, D24, D25, HI *.
Thrips tabaci (Onion thrips):
Sunflower leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs were infested with an aphid population of mixed ages. After an incubation period of 7 days, samples were checked for mortality.
The following compounds gave at least 80%> control of Thrips tabaci: Al, A2, A4, A5, A6, A7, A12, A13, A14, A15, A16, C2, C4, C5, C7, C13, C17, C19, C20, C21, C22, A86, A17, A19, A20, A27, A29, A30, A31, A59, A77, A78, A79, A82, A84, D24, Fl, Dl, D24, D3, D4, D5, D5*, D6, D8, D9, D10, Dl l, D12, D14, D15, D16, D18, D20, D21, D22, D23, E18, D24, D25, HI *.
Tetranychus urticae (Two-spotted spider mite):
Bean leaf discs on agar in 24-well microtiter plates were sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs are infested with mite populations of mixed ages. 8 days later, discs are checked for egg mortality, larval mortality, and adult mortality.
The following compound gave at least 80%> control of Tetranychus urticae: Al, A2, A3, A4, A5, A6, A7, A8, A9, A10, Al l, A12, A13, A14, A15, A16, B9, C2, C5, C13, C14, C17, C19, C22, A86, A17, A18, A19, A20, A25, A27, A28, A29, A30, A31, A35, A38, A40, A43, A45, A46, A49, A52, A56, A57, A58, A63, A77, A78, A79, A80, A81, A82, A83, A84, D24, Fl, D24, D3, D4, D5, D5*, D6, D8, D9, D10, Dl l, D12, D13, D14, D15, D18, D19, D20, D21, D23, F2, E5, E16, D24, D25
Biological examples of enantiomers
These examples illustrate the comparative insecticidal and acaricidal properties of compounds D24* and D24**. The tests were performed as follows: Spodoptera littoralis (systemic) (Egyptian cotton leaf worm)
Test compounds were applied by pipette into 24 well plates and mixed with agar. Salad seeds were placed on the agar and the multi well plate is closed by another plate which contains also agar. After 7 days the roots have absorbed the compound and the salad has grown into the lid plate. The salad leafs were now cut off into the lid plate. Spodoptera eggs were pipette through a plastic stencil on a humid gel blotting paper and the plate closed with it. The samples are checked for mortality, repellent effect, feeding behavior, and growth regulation 5 days after infestation.
Insects: Spodoptera littoralis %> Control at 200 ppm %> Control at 12.5 ppm
Figure imgf000326_0001
Plutella xylostella (Diamond back moth):
24-well microtiter plate (MTP) with artificial diet was treated with test solutions at an application rate of 200 ppm (concentration in well 18 ppm) by pipetting. After drying, the MTPs were infested with L2 larvae (7-12 per well). After an incubation period of 6 days, samples were checked for larval mortality and growth regulation.
Figure imgf000326_0002
Diabrotica balteata (Corn root worm):
A 24-well microtiter plate (MTP) with artificial diet was treated with test solutions at an application rate of 12.5 ppm (concentration in well 18 ppm) by pipetting. After drying, the MTP's were infested with L2 larvae (6-10 per well). After an incubation period of 5 days, samples were checked for larval mortality and growth regulation.
Figure imgf000326_0003
Thrips tabaci (Onion thrips):
Sunflower leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 50 ppm. After drying, the leaf discs were infested with a thrip population of mixed ages. After an incubation period of 7 days, samples were checked for mortality.
Figure imgf000326_0004
Tetranychus urticae (Two-spotted spider mite):
Bean leaf discs on agar in 24-well microtiter plates were sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs are infested with mite populations of mixed ages. 8 days later, discs are checked for egg mortality, larval mortality, and adult mortality.
Insects: Tetranychus urticae % Control at 200 ppm „^
Figure imgf000327_0001

Claims

Figure imgf000328_0001
QA1 QA2
P is PI, heterocyclyl or heterocyclyl substituted by one to five Z;
Figure imgf000328_0002
A1, A2, A3 and A4 are independently of each other C-H, C-R5, or nitrogen;
G1 is oxygen or sulfur;
R1 is hydrogen, Ci-C8alkyl, Q-Qalkoxy-, CrQalkylcarbonyl-, or Ci-C8alkoxycarbonyl-;
R2 is Ci-C8alkyl or Ci-C8alkyl substituted by one to five R6, C3-Ciocycloalkyl or C3-Ci0cycloalkyl substituted by one to five R7, aryl-Ci-C4alkylene- or aryl-Ci-C4alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl-Ci-C4alkylene- or heterocyclyl-Ci-C4alkylene- wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, Ci-C8alkylaminocarbonyl-Ci-C4 alkylene, Q- C8haloalkylaminocarbonyl-Ci-C alkylene, C3-C8cycloalkyl-aminocarbonyl-Ci-C alkylene, Ci-C6alkyl- 0-N=CH-, CrC6haloalkyl-0-N=CH-,
R3 is CrC8haloalkyl;
R4 is aryl or aryl substituted by one to five R9, or heteroaryl or heteroaryl substituted by one to five R9; each R5 is independently halogen, cyano, nitro, Ci-C8alkyl, Ci-C8haloalkyl, Ci-C8alkenyl, d- C8haloalkenyl, Ci-C8alkynyl, Ci-C8haloalkynyl, C3-Ciocycloalkyl, Ci-C8alkoxy-, Ci-C8haloalkoxy-, d- C8alkylthio-, Ci-C8haloalkylthio-, Ci-C8alkylsulfinyl-, Ci-C8haloalkylsulfinyl-, Ci-C8alkylsulfonyl-, or Ci-C8haloalkylsulfonyl-; each R6 is independently halogen, cyano, nitro, hydroxy, amino, CrQalkylamino, (Ci-C8alkyl)2amino, Ci-Cgalkylcarbonylamino, Ci-Cghaloalkylcarbonylamino, CpCgalkoxy-, Ci-Cghaloalkoxy-, aryloxy or aryloxy substituted by one to five R10, aryloxy-Ci-C4alkylene or aryloxy-Ci-C4alkylene wherein the aryl moiety is substituted by one to five R10, CpCgalkylcarbonyl-, Ci-Cgalkoxycarbonyl-, mercapto, Cp Cgalkylthio-, Ci-Cghaloalkylthio-, Ci-Cgalkylsulfinyl-, Ci-Cghaloalkylsulfinyl-, Ci-Cgalkylsulfonyl-, Q- Cghaloalkylsulfonyl-, aryl-C i-C4alkylthio- or aryl-Ci-C4alkylthio- wherein the aryl moiety is substituted by one to five R10;
each R7 is independently halogen, CpCgalkyl, d-Cgalkenyl, d-Cgalkynyl,
Figure imgf000329_0001
Q- Cghaloalkyl-0-N=; Ci-Cgalkoxy, Ci-Cgakoxycarbonyl;
each R8 is independently halogen, cyano, nitro, oxo, CpCgalkyl, Ci-Cghaloalkyl, Ci-Cgcyanoalkyl, C2- Cgalkenyl, C2-C8haloalkenyl, C2-C8alkynyl, C2-C8haloalkynyl, C3-Ci0cycloalkyl, C3-Ci0cycloalkyl-Ci- C4alkylene, hydroxy, Ci-C8alkoxy-, Ci-C8haloalkoxy-, mercapto, Ci-C8alkylthio-, Ci-C8haloalkylthio-, Ci-C8alkylsulfinyl-, Ci-C8haloalkylsulfinyl-, Ci-C8alkylsulfonyl-, Ci-C8haloalkylsulfonyl-, Cr
C8alkylaminosulfonyl, (Ci-C8alkyl)2aminosulfonyl-, Ci-C8alkylcarbonyl-, Ci-C8alkoxycarbonyl-, aryl or aryl substituted by one to five R10, heterocyclyl or heterocyclyl substituted by one to five R10, aryl-Q- C4alkylene or aryl-C rC4alkylene wherein the aryl moiety is substituted by one to five R10, heterocyclyl- Ci-C4alkylene or heterocyclyl-Ci-C4alkylene wherein the heterocyclyl moiety is substituted by one to five R10, aryloxy or aryloxy substituted by one to five R10, aryloxy-Ci-C4alkylene or aryloxy-Ci-C4alkylene wherein the aryl moiety is substituted by one to five R10;
each R9 is independently halogen, cyano, nitro, Ci-C8alkyl, Ci-C8haloalkyl, C2-C8alkenyl, C2-
C8haloalkenyl, C2-C8alkynyl, C2-C8haloalkynyl, hydroxy, Ci-C8alkoxy-, Ci-C8haloalkoxy-, mercapto, Cr C8alkylthio-, Ci-C8haloalkylthio-, Ci-C8alkylsulfinyl-, Ci-C8haloalkylsulfinyl-, Ci-C8alkylsulfonyl-, Q- C8haloalkylsulfonyl-, Ci-C8alkylcarbonyl-, Ci-C8alkoxycarbonyl-, aryl or aryl substituted by one to five R10, or heterocyclyl or heterocyclyl substituted by one to five R10;
each R10 is independently halogen, cyano, nitro, Ci-C4alkyl, Ci-C4haloalkyl, Ci-C4alkoxy-, or Q- C4haloalkoxy-;
each Z is independently halogen, Ci-Ci2alkyl or Ci-Ci2alkyl substituted by one to five R6, nitro, Cr Ci2alkoxy or Ci-Ci2alkoxy substituted by one to five R6, cyano, Ci-Ci2alkylsulfinyl, Ci-Ci2alkylsulfonyl, Ci-Ci2haloalkylsulfinyl, Ci-Ci2haloalkylsulfonyl, hydroxyl or thiol;
or a salt or N-oxide thereof.
2. A compound according to claim 1 wherein A1 is C-R5, A2 is C-H, A3 is C-H or nitrogen and A4 is C-H or nitrogen.
3. A compound according to claim 1 or claim 2 wherein G1 is oxygen.
4. A compound according to any one of claims 1 to 3, wherein P is PI or a heterocycle selected from HI to H9 3 ^N^N J
\=≡T(Z)k \=≡T(¾k \=≡/-(¾k \=≡ -(¾k
H1 H2 H3 H4
Figure imgf000330_0001
H5 H6 H7 H8 H9 k is 0, 1 or 2.
5. A compound according to any one of claims 1 to 4 wherein R1 is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl-.
6. A compound according to any one of claims 1 to 5 wherein R is Q-Cgalkyl or Q-Cgalkyl substituted by one to five R6, C3-Ci0cycloalkyl or C3-Ci0cycloalkyl substituted by one to five R7, aryl-Q- C4alkylene- or aryl-Ci-C4alkylene- wherein the aryl moiety is substituted by one to five R8, heterocyclyl- Ci-C4alkylene- or heterocyclyl-Ci-C4alkylene- wherein the heterocyclyl moiety is substituted by one to five R8, aryl or aryl substituted by one to five R8, heterocyclyl or heterocyclyl substituted by one to five R8, Ci-Cgalkylaminocarbonyl-Ci-C i alkylene, Ci-Cghaloalkylaminocarbonyl-Ci-C4 alkylene, C3- Cgcycloalkyl-aminocarbonyl-Ci-C i alkyle
Figure imgf000330_0002
R11 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, cyclopropyl, cyclopropyl-methyl, cyclobutyl, cyclobutyl-methyl, oxetanyl, thietanyl, trifluoroethyl, difluoroethyl, allyl, propargyl, cyanomethyl, benzyl, benzyl substituted by one to three R12, or R11 is pyridyl-methyl- or pyridyl -methyl- substituted by one to three R12;
each R12 is independently fluoro, chloro, bromo, trifluoromethyl, trifluoromethoxy, cyano or methoxy; wherein each aryl group is a phenyl group and each heterocyclyl group is independently selected from pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl,
tetrahydrothiophenyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl, benzothiazolyl, oxetanyl, thietanyl, oxo-thietanyl, dioxo-thietanyl, pyrrolidinyl, tetrahydrofuranyl, [l,3]dioxolanyl, piperidinyl, piperazinyl, [l,4]dioxanyl, and morpholinyl, 2,3-dihydro- benzofuranyl, benzo[l,3]dioxolanyl, and 2,3-dihydro-benzo[l,4]dioxinyl.
7. A compound according to claim 6 wherein R2 is Q-Cgalkyl or Q-Cgalkyl substituted by one to five R6, C3-Ciocycloalkyl or C3-Ciocycloalkyl substituted by one to five R7, phenyl-Ci-C4alkylene- or phenyl-Ci-C4alkylene- wherein the phenyl moiety is substituted by one to five R8, pyridyl-Ci-C4alkylene- or pyridyl-Ci-C4alkylene- wherein the pyridyl moiety is substituted by one to four R8, oxetanyl or oxetanyl substituted by one to five R8, thietanyl-Ci-C4 alkylene or thietanyl-Ci-C4 alkylene wherein the thietanyl moiety is substituted by one to five R8, oxo-thietanyl-Ci-C4 alkylene or oxo-thietanyl-Ci-C4 alkylene wherein the oxo-thietanyl moiety is substituted by one to five R8, dioxo-thietanyl-Ci-C4 alkylene or dioxo-thietanyl-Ci-C4 alkylene wherein the dioxo-thietanyl moiety is substituted by one to five R8, thietanyl or thietanyl substituted by one to five R8, oxo-thietanyl or oxo-thietanyl substituted by one to five R8, dioxo-thietanyl or dioxo-thietanyl substituted by one to five R8, Ci-Cgalkylaminocarbonyl-Ci-C4 alkylene, Ci-Cghaloalkylaminocarbonyl-Ci-C4 alkylene, or C3-Cgcycloalkyl-aminocarbonyl-Ci-C4 alkylene or group A
Figure imgf000331_0001
8. A compound according to any one of claims 1 to 7 wherein R is chlorodifluoromethyl trifluoromethyl.
A compound according to any one of claims 1 to 8 wherein R is aryl or aryl substituted by one to
10. A compound according to claim 1 , wherein
P is PI ;
QA is QA1 or QA2;
A1 is C-R5, A2 is C-H, A3 is C-H and A4 is C-H;
G1 is oxygen;
R1 is hydrogen;
R2 is Ci-Cgalkyl or Ci-Cgalkyl substituted by one to three halogen atoms, C3-Ciocycloalkyl or C3- Ciocycloalkyl substituted by one or two groups independently selected from fluoro and methyl, phenyl- Ci-C4alkylene- or phenyl-Ci-C4alkylene- wherein the phenyl moiety is substituted by one to five R8, pyridyl-Ci-C4 alkylene- or pyridyl-Ci-C4 alkylene- wherein the pyridyl moiety is substituted by one to four R8, thietanyl, oxo-thietanyl, dioxo-thietanyl, Ci-C4alkylaminocarbonyl-Ci-C4 alkylene, Q- C4haloalkylaminocarbonyl-Ci-C4 alkylene, C3-C6cycloalkyl-aminocarbonyl-Ci-C4 alkylene, or group A
Figure imgf000331_0002
R3 is trifluoromethyl;
R4 is 3,5-dichloro-phenyl;
R5 is methyl;
eeaacchh RR88 iiss iinnddependently bromo, chloro, fluoro, cyano or methyl;
R11 is methyl, ethyl or trifluoroethyl.
A compound of formula (IIA)
Figure imgf000332_0001
wherein QA, A1, A2, A3, and A4 are as defined for a compound of formula (IA) in any one of claims 1 to 10, G1 is oxygen, and R is hydroxy, Ci-Ci5alkoxy or halogen; or a salt or N-oxide thereof;
or a compound of formula (IIIA)
Figure imgf000332_0002
wherein QA, A1, A2, A3, A4 are as defined for a compound of formula (IA) in any one of claims 1 to 10,
X is a leaving group; or a salt or N-oxide thereof;
or a compound of
Figure imgf000332_0003
wherein A1, A2, A3, A4, R3 and R4 are as defined for a compound of formula (IA) in any one of claims 1 to 10, Px is P as defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, or a salt or N-oxide thereof;
or a compound of formula (XXIIIA) (xxiiiA)
Figure imgf000332_0004
wherein R3 and R4 are as defined for a compound of formula (IA) in any one of claims 1 to 10, or a salt or
N-oxide thereof;
or a compound of formula (XXVIA)
(XXVIA)
Figure imgf000332_0005
wherein R3 and R4 are as defined for a compound of formula (IA) in any one of claims 1 to 10, and X is a tin derivative, a boron derivative, a leaving group, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, or a salt or N-oxide thereof;
or a compound of formula (XXVIIA) (xxviiA)
Figure imgf000333_0001
wherein R3 and R4 are as defined for a compound of formula (IA) in any one of claims 1 to 10, and X is a tin derivative, a boron derivative, a leaving group, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, or a salt or N-oxide thereof;
or a compound of formula (XXVIA')
Figure imgf000333_0002
wherein R and R are as defined for the compounds of formula (IA) in any one of claims 1 to 10 and X is CI, Br or I, or a salt or N-oxide thereof;
or a compound of formula (XXVIIA')
Figure imgf000333_0003
wherein R3 and R4 and as defined for the compound of formula (IA) in any one of claims 1 to 10 and X is CI, Br or I, or a salt or N-oxide thereof;
or a compound of formula (XXXVIA) (XXXVIA)
Figure imgf000333_0004
wherein R3 and R4 are as defined for a compound of formula (IA) in any one of claims 1 to 10, or a salt or N-oxide thereof;
or a compound of formula (XXXVIIA) (XXXVIIA)
Figure imgf000333_0005
wherein R3 and R4 are as defined for a compound of formula (IA) in any one of claims 1 to 10, or a salt or N-oxide thereof;
or a compound of formula (XXXVIIIA) (XXXVI I IA)
Figure imgf000334_0001
wherein R3 and R4 are as defined for a compound of formula (IA) in any one of claims 1 to 10, and X is a tin derivative, a boron derivative, a leaving group, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, or a salt or N-oxide thereof;
or a compound of formula (LA)
Figure imgf000334_0002
wherein R3, R4 , A1, A2, A3, A4 and P are as defined for the compound of formula (IA) in any one of claims 1 to 10, or a salt or N-oxide thereof; or
or a compound of formula (LXA)
Figure imgf000334_0003
(LXA)
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) in any one of claims 1 to 10 and Px is P as defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or d- Ci5alkoxy, or a salt or N-oxide thereof;
or a compound of formula (LIXA)
Figure imgf000334_0004
(LIXA)
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) in any one of claims 1 to 10 and Px is P as defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or d- Ci5alkoxy, or a salt or N-oxide thereof, or a salt or N-oxide thereof;
or a compound of formula (LIIA)
wherein R3 and R4 are as defined for the compound of formula (IA) in any one of claims 1 to 10, or a salt or N-oxide thereof;
or a compound of formula (LIIIA)
Figure imgf000335_0002
(LIIIA)
wherein R3 and R4 are as defined for the compound of formula (IA) in any one of claims 1 to 10, and each X independently represents CI, Br or I, or a salt or N-oxide thereof;
or a compound of formula (LVA)
Figure imgf000335_0003
(LVA)
wherein R3, R4 , A1, A2, A3 and A4 are as defined for the compound of formula (IA) in any one of claims 1 to 10 and Px is P as defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or Cr Ci5alkoxy, or a salt or N-oxide thereof;
or a compound of formula (LVIA)
Figure imgf000335_0004
wherein R3, R4 , A1, A2, A3 and A4 are as defined for the compound of formula (IA) in any one of claims 1 to 10 and Px is P as defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or Cr Ci5alkoxy, or a salt or N-oxide thereof.
12. A mixture comprising a compound of formula (IA) as defined in any one of claims 1 to 10 and a compound of formula IB
Figure imgf000336_0001
wherein Q is Q 1 or Q 2
Figure imgf000336_0002
QB1 QB2
wherein A1, A2, A3, A4, P, R3 and R4 are as defined for the compound of formula (IA) in any one of claims 1 to 10; and wherein the mixture is enriched for the compound of formula (IA).
13. A mixture comprising compound of formula (IIA) as defined in claim 11 and a compound of formula (IIB)
Figure imgf000336_0003
wherein A1, A2, A3, and A4 are as defined for a compound of formula (IA) in any one of claims 1 to 10, QB is as defined for a compound of formula (IB) in claim 12, G1 is oxygen, and R is hydroxy, Cp Ci5alkoxy or halogen, and wherein the mixture is enriched for the compound of formula (IIA); or
a mixture comprising compound of formula (ΙΠΑ) as defined in claim 11 and a compound of formula (IIIB)
Figure imgf000336_0004
wherein A1, A2, A3, A4 are as defined for a compound of formula (IA) as defined in any one of claims 1 to 10, QB is as defined for a compound of formula (IB) in claim 12, and XB is a leaving group, and wherein the mixture is enriched for the compound of formula (IIIA); or
a mixture comprising compound of formula (XXVA) as defined in claim 11 and a compound of formula (XXVB)
(XXVB)
Figure imgf000336_0005
wherein A1, A2, A3, A4, R3 and R4 are as defined for a compound of formula (IA) in any one of claims 1 to 10, Px is P as defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, and wherein the mixture is enriched for the compound of formula (XXVA); or
a mixture comprising compound of formula (XXIIIA) as defined in claim 11 and a compound of formula (XXIIIB)
Figure imgf000337_0001
wherein R and R are as defined for a compound of formula (IA) in any one of claims 1 to 10, and wherein the mixture is enriched for the compound of formula (XXIIIA); or
a mixture comprising compound of formula (XXVIA) as defined in claim 11 and a compound of formula (XXVIB)
(XXVIB)
Figure imgf000337_0002
wherein R3 and R4 are as defined for a compound of formula (IA) in any one of claims 1 to 10, and X is a tin derivative, a boron derivative, a leaving group, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, and wherein the mixture is enriched for the compound of formula (XXVIA); or
a mixture comprising a compound of formula (XXVIA') as defined in claim 11 and a compound of formula (XXVIB ')
R4- Λ (XXVIB') wherein R3 and R4 are as defined for the compound of formula (IA) in any one of claims 1 to 10, X is CI, Br or I, and wherein the mixture is enriched for compounds of formula (XXVIA'); or
a mixture comprising compound of formula (XXVIIA) as defined in claim 11 and a compound of formula (XXVIIB)
Figure imgf000337_0003
wherein R3 and R4 are as defined for a compound of formula (IA) in any one of claims 1 to 10, and X is a tin derivative, a boron derivative, a leaving group, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, and wherein the mixture is enriched for the compound of formula (XXVIIA); or
a mixture comprising a compound of formula (XXVIIA') as defined in claim 11 and a compound of formula (XXVIIB ') (ΧΧνΐΙΒ')
Figure imgf000338_0001
wherein R3 and R4 are as defined for the compound of formula (IA) in any one of claims 1 to 10 and X is CI, Br or I, and wherein the mixture is enriched for compounds of formula (XXVIIA'); or
a mixture comprising compound of formula (XXXVIA) as defined in claim 11 and a compound of formula (XXXVIB)
(XXXVIB)
Figure imgf000338_0002
wherein R and R are as defined for a compound of formula (IA) in any one of claims 1 to 10, and wherein the mixture is enriched for the compound of formula (XXXVIA); or
a mixture comprising compound of formula (XXXVIIA) as defined in claim 11 and a compound of formula (XXXVIIB) (XXXVI IB)
Figure imgf000338_0003
wherein R3 and R4 are as defined for a compound of formula (IA) in any one of claims 1 to 10, and wherein the mixture is enriched for the compound of formula (XXXVIIA); or
a mixture comprising compound of formula (XXXVIIIA) as defined in claim 11 and a compound of formula (XXXVIIB)
(XXXVIIIB)
Figure imgf000338_0004
wherein R3 and R4 are as defined for a compound of formula (IA) in any one of claims 1 to 10, and X is a tin derivative, a boron derivative, a leaving group, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, and wherein the mixture is enriched for the compound of formula (XXXVIIIA); or
a mixture comprising a compound of formula (LA) as defined in claim 11 and a compound of formula (LB)
Figure imgf000338_0005
wherein R3, R4 , A1, A2, A3, A4 and P as defined for the compound of formula (IA) in any one of claims 1 to 10, and wherein the mixture is enriched for compounds of formula (LA); or
a mixture comprising a compound of formula (LXA) as defined in claim 11 and a compound of formula (LXB)
Figure imgf000339_0001
(LXB)
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) in any one of claims 1 to 10 and Px is P as defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or Cr
Ci5alkoxy, and wherein the mixture is enriched for compounds of formula (LXA); or
a mixture comprising a compound of formula (LIXA) as defined in claim 11 and a compound of formula (LIXB)
Figure imgf000339_0002
(LIXB)
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) and Px is P as defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, and wherein the mixture is enriched for compounds of formula (LIXA) or
a mixture comprising a compound of formula (LIIA) as defined above and a compound of formula (LIIB)
Figure imgf000339_0003
wherein R and R are as defined for the compound of formula (IA) in any one of claims 1 to 10, and wherein the mixture is enriched for compounds of formula (LIIA); or
a mixture comprising a compound of formula (LIIIA) as defined in claim 11 and a compound of formula (LIIIB)
Figure imgf000340_0001
(LIIIB)
wherein R3 and R4 are as defined for the compound of formula (IA) in any one of claims 1 to 10, and each X independently represents CI, Br or I, and wherein the mixture is enriched for compounds of formula (LIIIA); or
a mixture comprising a compound of formula (LVA) as defined in claim 11 and a compound of formula (LVB)
Figure imgf000340_0002
(LVB)
wherein R3 and R4, A1, A2, A3, A4 are as defined for the compounds of formula (IA) in any one of claims 1 to 10, Px is P as defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or d- Ci5alkoxy, and wherein the mixture is enriched for compounds of formula (LVA); or
a mixture comprising a compound of formula (LVIA) as defined in claim 11 and a compound of formula (LVIB)
Figure imgf000340_0003
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) in any one of claims 1 to 10 and Px is P as defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or Cr
Ci5alkoxy, and wherein the mixture is enriched for compounds of formula (LVIA).
14. A method of controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (IA) as defined in any one of claims 1 to 10 or a mixture as defined in claim 12.
15. An insecticidal, acaricidal, nematicidal or molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (IA) as defined in any one of claims 1 to 10 or a mixture as defined in claim 12.
16. An insecticidal, acaricidal, nematicidal or molluscicidal composition according to claim 15 comprising at least one additional compound having biological activity.
17. A combination product comprising a pesticidally effective amount of a component A and a pesticidally effective amount of component B, wherein component A is a compound of formula (IA) as defined in any one of claims 1 to 10, or a mixture as defined in claim 12, and compound B is
5 imidacloprid, enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, fipronil, ivermectin, omeprazole, tiamulin, benazepril, milbemycin, cyromazine, thiamethoxam, pyriprole, deltamethrin, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, metaflumizone, moxidectin, methoprene (including S-methoprene), clorsulon, pyrantel, amitraz, triclabendazole, avermectin, abamectin, 10 emamectin, eprinomectin, doramectin, selamectin, nemadectin, albendazole, cambendazole,
fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, tetramisole, levamisole, pyrantel pamoate, oxantel, morantel, triclabendazole, epsiprantel, fipronil, lufenuron, ecdysone or tebufenozide.
15 18. A process for the preparation of a compound of formula (XIX)
Figure imgf000341_0001
wherein
Ar is group A
Figure imgf000341_0002
(A)
20 R3, R4, A1, A2, A3, A4 are as defined for the compound of formula (IA) in any one of claims 1 to 10 , and Px is P as defined in claim 1 , a leaving group, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, or a salt or N-oxide thereof;
comprising dehydrating a compound of formula (LX)
Figure imgf000342_0001
wherein R3, R4 and Ar are as defined for the compound of formula (XIX);
with a suitable acidic catalyst or a suitable activation agent and a suitable base.
A process for the preparation of a compound of formula (LX)
Figure imgf000342_0002
wherein R3, R4 and Ar are as defined for the compound of formula (XIX) in claim 18;
comprising reacting a compound of formula (LIX) or (LVI)
Figure imgf000342_0003
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) in any one of claims 1 to 10 and Px is P as defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or Cr Ci5alkoxy; with a source of H2 and CO in the presence of a catalyst comprising a complex of a transition metal and a suitable ligand.
20. A compound of formula (LX)
Figure imgf000342_0004
(LX)
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) in any one of claims 1 to 10 and Px is P as defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or Cr Ci5alkoxy, or a salt or N-oxide thereof; or
a compound of formula (LIX)
Figure imgf000343_0001
(LIX)
wherein R3, R4 , A1, A2, A3, A4 are as defined for the compound of formula (IA) in any one of claims 1 to 10 and Px is P as defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or d- Ci5alkoxy, or a salt or N-oxide thereof; or
a compound of formula (LII)
Figure imgf000343_0002
wherein R3 and R4 are as defined for the compound of formula (IA) in any one of claims 1 to 10, or a salt or N-oxide thereof; or
a compound of formula (LIII)
Figure imgf000343_0003
wherein R3 and R4 are as defined for the compound of formula (IA) in any one of claims 1 to 10, and each X independently represents CI, Br or I, or a salt or N-oxide thereof; or
a compound of formula (XXVI)
Figure imgf000343_0004
wherein R3 and R4 are as defined for the compound of formula (IA) in any one of claims 1 to 10 and X is CI, Br or I; or a salt or N-oxide thereof; or
a compound of formula (XXXVI)
Figure imgf000343_0005
(xxxvi)
wherein R3 and R4 are as defined for the compound of formula (IA) in any one of claims 1 to 10, or a salt of N-oxide thereof; or
a compound of formula (LI)
Figure imgf000344_0001
wherein R3 and R4 are as defined for the compound of formula (IA) in any one of claims 1 to 10; or a salt or N-oxide thereof; or
a compound of formula (LV)
Figure imgf000344_0002
(LV)
wherein R3, R4 , A1, A2, A3 and A4 are as defined for the compound of formula (IA) and Px is P defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, or a s;
oxide thereof; or
a compound of formula (LVI)
Figure imgf000344_0003
wherein R3, R4 , A1, A2, A3 and A4 are as defined for the compound of formula (IA) and Px is P as defined in claim 1, a leaving group, or C(0)R wherein R is halogen, OH or Ci-Ci5alkoxy, or a salt or N- oxide thereof.
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