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US20220169621A1 - Oxadiazoles for use in controlling phytopathogenic fungi - Google Patents

Oxadiazoles for use in controlling phytopathogenic fungi Download PDF

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Publication number
US20220169621A1
US20220169621A1 US17/651,439 US202217651439A US2022169621A1 US 20220169621 A1 US20220169621 A1 US 20220169621A1 US 202217651439 A US202217651439 A US 202217651439A US 2022169621 A1 US2022169621 A1 US 2022169621A1
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alkyl
alkoxy
cycloalkyl
haloalkyl
haloalkoxy
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US17/651,439
Inventor
Paras Raybhan Bhujade
Rajesh Pawar
Maruti N. Naik
Rajender Kumar Potlapally
Nitin Ramesh Tembhare
Santosh Shridhar Autkar
Ruchi Garg
Hagalavadi M. Venkatesha
Alexander G.M. Klausener
Visannagari Ramakrishna
Nilesh Bharat Adhav
Pooja Trivedi
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PI Industries Ltd
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PI Industries Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • 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
    • A01N43/82—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 three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • 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

Definitions

  • the present invention relates to novel oxadiazoles, N-oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof and plurality of processes for preparing the same. Further, the present invention relates to a combination and a composition comprising novel oxadiazoles of the present invention. Still further, the present invention relates to a use of novel oxadiazoles of the present invention for controlling or preventing phytopathogenic fungi and to a method for controlling or preventing phytopathogenic harmful fungi.
  • Oxadiazoles have already been disclosed in the literature. For example in JP56065881, JP63 162680, JPS6061573, JPS6296480, JPS6051188, JP2005336101, WO2005051932, EP3165093, EP3165094, EP3167716, EP3165093, JP2017190296, U.S. Pat. No.
  • oxadiazole compounds reported in the above literature have disadvantages in certain aspects, such as that they exhibit a narrow spectrum of application or they do not have satisfactory fungicidal activity, particularly at low application rates.
  • This objective is achieved by the using oxadiazoles of the present invention for controlling or preventing phytopathogenic fungi.
  • the present invention relates to novel oxadiazoles of Formula I.
  • R 1 , L 1 , A, L 2 and R 10 are as defined in the detailed description.
  • the present invention further relates to a combination comprising novel oxadizoles of the present invention and at least one further pesticidally active substance for effectively controlling or preventing phytopathogenic fungi which are difficult to control or prevent.
  • the present invention still further relates to a composition comprising novel oxadizoles or novel oxadiazoles in combination with further pesticidally active substance.
  • the present invention still further relates to a method and use of novel oxadizoles, combinations or compositions thereof for controlling and or preventing plant diseases, particularly phytopathogenic fungi.
  • compositions comprising, “comprising”, “includes”, “including”, “has”, “having”, “contains”, “containing”, “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated.
  • a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.
  • transitional phrase “consisting essentially of” is used to define a composition or method that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention.
  • the term “consisting essentially of” occupies a middle ground between “comprising” and “consisting of”.
  • “or” refers to an inclusive “or” and not to an exclusive “or”.
  • a condition A “or” B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
  • the term “invertebrate pest” includes arthropods, gastropods and nematodes of economic importance as pests.
  • arthropod includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans.
  • gastropod includes snails, slugs and other Stylommatophora.
  • nematode refers to a living organism of the Phylum Nematoda.
  • helminths includes roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), acanthocephala and tapeworms (Cestoda).
  • invertebrate pest control means inhibition of invertebrate pest development (including mortality, feeding reduction, and/or mating disruption), and related expressions are defined analogously.
  • agronomic refers to the production of field crops such as for food and fiber and includes the growth of corn, soybeans and other legumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).
  • wheat e.g., wheat, oats, barley, rye, rice, maize
  • leafy vegetables e.g., lettuce, cabbage, and other cole crops
  • fruiting vegetables e.g., tomatoes, pepper, eggplant, crucifers and cucurbits
  • potatoes e.g., sweet potatoes, grapes, cotton, tree fruits (e.g.
  • nonagronomic refers to other than field crops, such as horticultural crops (e.g., greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial and industrial structures, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), wood products, stored product, agro-forestry and vegetation management, public health (i.e. human) and animal health (e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife) applications.
  • horticultural crops e.g., greenhouse, nursery or ornamental plants not grown in a field
  • turf e.g., sod farm, pasture, golf course, lawn, sports field, etc.
  • wood products e.g., stored product, agro-forestry and vegetation management
  • public health i.e. human
  • animal health e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife
  • Nonagronomic applications include protecting an animal from an invertebrate parasitic pest by administering a parasiticidally effective (i.e. biologically effective) amount of a compound of the present invention, typically in the form of a composition formulated for veterinary use, to the animal to be protected.
  • a parasiticidally effective (i.e. biologically effective) amount of a compound of the present invention typically in the form of a composition formulated for veterinary use, to the animal to be protected.
  • parasiticidal i.e. biologically effective
  • Parasiticidally refers to observable effects on an invertebrate parasite pest to provide protection of an animal from the pest. Parasiticidal effects typically relate to diminishing the occurrence or activity of the target invertebrate parasitic pest.
  • Such effects on the pest include necrosis, death, retarded growth, diminished mobility or lessened ability to remain on or in the host animal, reduced feeding and inhibition of reproduction.
  • These effects on invertebrate parasite pests provide control (including prevention, reduction or elimination) of parasitic infestation or infection of the animal.
  • the compounds of the present disclosure may be present either in pure form or as mixtures of different possible isomeric forms such as stereoisomers or constitutional isomers.
  • the various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixtures of these isomers fall within the scope of the claims of the present disclosure.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other isomer(s) or when separated from the other isomer(s). Additionally, the person skilled in the art knows processes or methods or technology to separate, enrich, and/or to selectively prepare said isomers.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” or —N(alkyl) or alkylcarbonylalkyl or alkylsuphonylamino includes straight-chain or branched Ci to C24 alkyl, preferably Ci to C 15 alkyl, more preferably Ci to C 10 alkyl, most preferably Ci to C 6 alkyl.
  • Non limiting examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1.1.2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropy
  • the alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl
  • the part of the composite substituent at the start for example the cycloalkyl
  • other radicals for example alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy and the like, are at the end.
  • alkenyl used either alone or in compound words includes straight-chain or branched C 2 to C 24 alkenes, preferably C 2 to C 15 alkenes, more preferably C 2 to C 10 alkenes, most preferably C 2 to C6 alkenes.
  • Non limiting examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1.2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-prop
  • Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as a part of a composite substituent, for example haloalkenyl and the like, unless defined specifically elsewhere.
  • Non limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-di methyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentyn
  • alkynyl as a part of a composite substituent, for example haloalkynyl etc., unless specifically defined elsewhere.
  • alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
  • cycloalkyl means alkyl closed to form a ring. Non limiting examples include cyclopropyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere.
  • cycloalkenyl means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Non limiting examples include cyclopropenyl, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenylalkyl etc., unless specifically defined elsewhere.
  • cycloalkynyl means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. Non limiting examples include cyclopropynyl, cyclopentynyl and cyclohexynyl. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.
  • cycloalkoxy cycloalkenyloxy
  • cycloalkoxy cycloalkenyloxy
  • Non limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as a part of a composite substituent, for example cycloalkoxy alkyl etc., unless specifically defined elsewhere.
  • halogen either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different.
  • haloalkyl include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl, and 1,1,1-trifluoroprop-2-yl. This definition also applies to haloalkyl as a part
  • haloalkenyl haloalkynyl
  • alkenyl and alkynyl groups are present as a part of the substituent.
  • haloalkoxy means straight-chain or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above.
  • Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-
  • haloalkylthio means straight-chain or branched alkylthio groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above.
  • Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,
  • haloalkylsulfinyl include CF 3 S(O), CCl 3 S(O), CF 3 CH 2 S(O) and CF 3 CF 2 S(O).
  • haloalkylsulfonyl include CF 3 S(O) 2 , CCl 3 S(O) 2 , CF 3 CH 2 S(O) 2 and CF 3 CF 2 S(O) 2 .
  • hydroxy means —OH
  • Amino means —NRR, wherein R can be H or any possible substituent such as alkyl.
  • Carbonyl means —C(O)—
  • carbonyloxy means —OC(O)—
  • sulfinyl means SO
  • sulfonyl means S(O) 2 .
  • alkoxy used either alone or in compound words included Ci to C 24 alkoxy, preferably Ci to C 15 alkoxy, more preferably Ci to Cio alkoxy, most preferably Ci to C 6 alkoxy.
  • alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethoxy
  • alkoxyalkyl denotes alkoxy substitution on alkyl.
  • alkoxyalkyl include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2.
  • alkoxyalkoxy denotes alkoxy substitution on alkoxy.
  • alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio
  • Halocycloalkyl halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxylalkyl, and the like, are defined analogously to the above examples.
  • alkylthioalkyl denotes alkylthio substitution on alkyl.
  • alkylthioalkyl include —CH 2 SCH 2 , —CH 2 SCH 2 CH 2 , CH 2 CH 2 SCH 2 , CH 3 CH2CH2CH2SCH2 and CH3CH2SCH2CH2.
  • Alkylthioalkoxy denotes alkylthio substitution on alkoxy.
  • cycloalkylalkylamino denotes cycloalkyl substitution on alkyl amino.
  • alkoxyalkoxyalkyl alkylaminoalkyl, dialkylaminoalkyl, cycloalkylaminoalkyl, cycloalkylaminocarbonyl and the like, are defined analogously to “alkylthioalkyl” or cycloalkylalkylamino.
  • alkoxycarbonyl is an alkoxy group bonded to a skeleton via a carbonyl group (—CO—). This definition also applies to alkoxycarbonyl as a part of a composite substituent, for example cycloalkylalkoxycarbonyl and the like, unless specifically defined elsewhere.
  • alkoxycarbonylalkylamino denotes alkoxy carbonyl substitution on alkyl amino.
  • Alkylcarbonylalkylamino denotes alkyl carbonyl substitution on alkyl amino.
  • alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl and the like are defined analogously.
  • alkylsulfinyl include methylsulphinyl, ethylsulphinyl, propylsulphinyl, methylethylsulphinyl, butylsulphinyl, 1-methylpropylsulphinyl, 2-methylpropylsulphinyl, 1,1-dimethylethylsulphinyl, pentylsulphinyl, 1-methylbutylsulphinyl, 2-methylbutylsulphinyl, 3-methylbutylsulphinyl, 2,2-dimethylpropylsulphinyl, 1-ethylpropylsulphinyl, hexylsulphinyl, 1,1-dimethylpropylsulphinyl, 1,2-dimethylpropylsulphinyl, 1-methylpentylsulphinyl, 2-methylpentylsulphinyl, 3-methylpentylsulphinyl, 4-methylpentylsulphiny
  • arylsulfinyl includes Ar—S(O), wherein Ar can be any carbocycle or heterocycle. This definition also applies to alkylsulphinyl as a part of a composite substituent, for example haloalkylsulphinyl etc., unless specifically defined elsewhere.
  • alkylsulfonyl include methylsulphonyl, ethylsulphonyl, propylsulphonyl, 1-methyl ethylsulphonyl, butylsulphonyl, 1-methylpropylsulphonyl, 2-methylpropylsulphonyl, 1,1-dimethylethylsulphonyl, pentylsulphonyl, 1-methylbutylsulphonyl, 2-methylbutylsulphonyl, 3-methylbutylsulphonyl, 2,2-dimethylpropylsulphonyl, 1-ethylpropylsulphonyl, hexylsulphonyl, 1,1-dimethylpropylsulphonyl, 1,2-dimethylpropylsulphonyl, 1-methylpentylsulphonyl, 2-methylpentylsulphonyl, 3-methylpentylsulphonyl, 4-methylp
  • arylsulfonyl includes Ar—S(O) 2 , wherein Ar can be any carbocycle or heterocycle. This definition also applies to alkylsulphonyl as a part of a composite substituent, for example alkylsulphonylalkyl etc., unless defined elsewhere.
  • alkylamino “dialkylamino”, and the like, are defined analogously to the above examples.
  • carrier includes “aromatic carbocyclic ring system” and “nonaromatic carbocylic ring system” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which ring may be aromatic or non-aromatic (where aromatic indicates that the Huckel rule is satisfied and non-aromatic indicates that the Huckel rule is not satisfied).
  • hetero in connection with rings refers to a ring in which at least one ring atom is not carbon and which can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs.
  • heteroaryl or “aromatic heterocyclic” means 5 or 6-membered, fully unsaturated monocyclic ring system containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur; if the ring contains more than one oxygen atom, they are not directly adjacent; 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom as ring members, for example (but not limited thereto) furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,
  • 6-membered heteroaryl which contains one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain, respectively, one to three and one to four nitrogen atoms as ring members, for example (but not limited thereto) 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl; benzofused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulphur atom: for example (but not limited to) indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5
  • heteroaryl as a part of a composite substituent, for example heteroarylalkyl etc., unless specifically defined elsewhere.
  • non-aromatic heterocycle or “non-aromatic heterocyclic” means three- to fifteen-membered, preferably three- to twelve-membered, saturated or partially unsaturated heterocycle containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur: mono, bi- or tricyclic heterocycles which contain, in addition to carbon ring members, one to three nitrogen atoms and/or one oxygen or sulphur atom or one or two oxygen and/or sulphur atoms; if the ring contains more than one oxygen atom, they are not directly adjacent; for example (hut not limited to) oxetanyl, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-
  • trialkylsilyl includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom such as trimethylsilyl, triethylsilyl and t-butyl-dimethylsilyl.
  • halotrialkylsilyl denotes at least one of the three alkyl radicals is partially or fully substituted with halogen atoms which may be the same or different.
  • alkoxytrialkylsilyl denotes at least one of the three alkyl radicals is substituted with one or more alkoxy radicals which may be the same or different.
  • trialkylsilyloxy denotes a trialkylsilyl moiety attached through oxygen.
  • alkylcarbonyl examples include C(O)CH C(O)CH 2 CH 2 CH 3 and C(O)CH(CH 3 ) 2 .
  • haloalkylsufonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkyl amino and the like are defined analogously
  • amide means A-R′C ⁇ ONR′′—B, wherein R′ and R′′ indicates substituents and A and B indicate any group.
  • thioamide means A-R′C ⁇ SNR′′—B, wherein R′ and R′′ indicates substituents and A and B indicate any group.
  • Ci-C alkylsulfonyl designates methylsulfonyl through propylsulfonyl
  • C 2 alkoxyalkyl designates CH 3 OCH 2
  • C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 ), CH 3 OCH 2 CH 2 or CH 3 CH 2 OCH 2
  • C 4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
  • inventive compounds of the present invention may, if appropriate, be present as mixtures of different possible isomeric forms, especially of stereoisomers, for example E and Z, threo and erythro, and also optical isomers, but if appropriate also of tautomers. Both the E and the Z isomers, and also the threo and erythro isomers, and the optical isomers, any desired mixtures of these isomers and the possible tautomeric forms are disclosed and claimed.
  • pest for the purpose of the present disclosure includes but is not limited to fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects and rodents.
  • Plant is understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which are protectable and non-protectable by plant breeders' rights.
  • plant includes a living organism of the kind exemplified by trees, shrubs, herbs, grasses, ferns, and mosses, typically growing in a site, absorbing water and required substances through its roots, and synthesizing nutrients in its leaves by photosynthesis.
  • plants for the purpose of the present invention include but are not limited to agricultural crops such as wheat, rye, barley, triticale, oats or rice; beet, e.g. sugar beet or fodder beet; fruits and fruit trees, such as pomes, stone fruits or soft fruits, e.g.
  • leguminous plants such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit and citrus trees, such as oranges, lemons, grapefruits or mandarins; any horticultural plants, vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; larvaceous plants, such as avocados, cinnamon or camphor; cucurbitaceae; oleaginous plants; energy and raw material plants, such as cereals, corn, soybean, other leguminous plants, rape, sugar cane or oil palm; tobacco; nuts; coffee; tea; cacao
  • the plant for the purpose of the present invention include but is not limited to cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and vegetables, ornamentals, any floricultural plants and other plants for use of human and animals.
  • plant parts is understood to mean all parts and organs of plants above and below the ground.
  • plant parts includes but is not limited to cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots including taproots, lateral roots, root hairs, root apex, root cap, rhizomes, slips, shoots, fruits, fruit bodies, bark, stem, buds, auxiliary buds, meristems, nodes and internodes.
  • locus thereof includes soil, surroundings of plant or plant parts and equipment or tools used before, during or after sowing/planting a plant or a plant part.
  • compositions optionally comprising other compatible compounds to a plant or a plant material or locus thereof include application by a technique known to a person skilled in the art which include but is not limited to spraying, coating, dipping, fumigating, impregnating, injecting and dusting.
  • adhered means adhered to a plant or plant part either physically or chemically including impregnation.
  • novel oxadizole compounds of the present invention are represent by Formula I, N-oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof;
  • R 1 is Ci-C2-haloalkyl
  • A is an aromatic or non-aromatic carbocyclic ring, wherein the ring members of the non-aromatic carbocyclic ring are selected from C, C( ⁇ 0), C( ⁇ S), C( ⁇ CR 2a R 3a ) and C ⁇ NR 6 ; or
  • A is unsubstituted or is substituted with one or more identical or different R A groups
  • L 2 is a fragment selected from the group of
  • k is an integer ranging from 0 to 4; an expression “#” on the left side indicates the point of attachment to A, and an expression “*” on the right side indicates the point of attachment to R 10 ;
  • R 2 , R 3 , R 2a , R 3a , R 2b , R 3b , R 2c , R 3c , R 2d , R 3d , R 2e , R 3e , R 7 and R 8 are independently selected from hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, Ci-C 4 -halo alkyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, Ci-C 4 -alkoxy or C 1 -C 4 -haloalkoxy, or
  • R 2 and R 3 ; R 2a and R 3s ; R 2b and R 3b ; R 2e and R 3e ; R 2d and R 3d ; R 2e and R 3e ; and or R 7 and R 8 together with the atoms to which they are attached may form 3- to 5-membered non-aromatic carbocylic ring or heterocyclic ring which may be optionally substituted with halogen, Ci-C 2 -alkyl, Ci-C 2 -haloalkyl or Ci-C 2 -alkoxy;
  • R 10 is selected from the group of hydrogen, halogen, hydroxy, cyano, —OR 12 , —NR 13 R 14 , nitro, —SH, —SCN, —COR 15 , —C( ⁇ O)OR 12 , —C( ⁇ O)NR 13 R 14 , —NR 13 C( ⁇ O)R 15 , —O(C ⁇ O)R 15 , —O(C ⁇ O)NR 13 R 14 , —C( ⁇ NOR 13 )R 15 , —NR 13 SO 2 R 16 , —CSR 16 , —C( ⁇ S)OR 12 , —C( ⁇ S)NR 13 R 14 , —NR 13 C( ⁇ S)R 15 , —O(C ⁇ S)R 15 , —O(C ⁇ S)NR 13 R 14 , —O(C ⁇ S)SR 16 , —N ⁇ C(R 15 ) 2 , —NHCN, —SO 2 NHCN, —C( ⁇ O
  • a carbon atom of R 1 from the oxadiazole ring bears at least two fluorine atoms; and the 9 carbon atom of R 1 from the oxadiazole ring in case of C2-haloalkyl bears at least one fluorine atom.
  • the present invention relates a compound of Formula I, wherein:
  • R 1 is trifluoroalkyl
  • L 1 is a direct bond
  • A is a phenyl ring or pyridyl ring; wherein phenyl or pyridyl ring is unsubstituted or substituted with one or more identical or different R A groups,
  • L 2 is a fragment selected from the group of
  • k is an integer ranging from 0 to 1; an expression “#” on the left side indicates the point of attachment to A, and an expression “*” on the right side indicates the point of attachment to R 10 ;
  • R 7 and R 8 are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, or C 1 -C 4 -alkoxy;
  • R 9 is selected from the group consisting of Ci-Ce-alkyl, C 2 -C 6 -alkenyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, and C 3 -Cs-cycloalkyl;
  • R 10 is selected from the group of Ci-Ce-alkyl, C 2 -Ce-alkenyl, C 2 -Ce-alkynyl, Ci-C6-haloalkyl, C 2 -C6-haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -Cs-cycloalkyl, C 3 -Cs-halocycloalkyl, Ci-C 6 -alkyl-C 3 -Cs-cycloalkyl, C 3 -Cs-cycloalkyl-Ci-C 6 -alkyl, C 3 -C 8 -cycloalkyl-Ci-CVcycloalkyl, C 3 -Cs-halocycloalkyl-Ci-Ce-alkyl, Ci-Ce-alkyl-Cs-Cs-cycloalkyl-Ci-Ce-alkyl, Ci-C 6 -alkoxy-Ci-C 6
  • R 9 and R 10 together with the atoms to which they are attached may form a 3- to 10-membered heterocyclic ring or ring system which may be optionally substituted with R 17 ; wherein the heteroatom of the heterocyclic ring or ring system is selected from N, O and S(O) 0-2 .
  • the compound of Formula I is selected from the group consisting of:
  • 6 -sulfanoric (3,4-difluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/. 6 -sulfanoric; methyl((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)(4-((4-(trifluoromethyl)pyridin-2-yl)oxyphenyl)-′/.
  • 6 -sulfanoric (4-chlorophenyl)(methyl) (3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/. 6 -sulfanoric; methyl(thiazol-2-yl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/. 6 -sulfanoric; (4-fluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/.
  • 6 -sulfanone (2-fluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl((benzyl)imino)-′/. 6 -sulfanone; 4-((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-1,4-′/.
  • 6 -sulfanoric N-((4-fluorophenyl)(methyl)(oxo)-/. 6 -sulfaneylidene)-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide; ((2,4-difluorophenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.
  • 6 -sulfanoric ((2-fluoro-4-methoxyphenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/. 6 -sulfanoric; ((2-fluorophenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.
  • 6 -sulfanoric ((2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(4-methoxyphenyl)(methyl)-X 6 -sulfanone; ((2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)(phenyl)-′/. 6 -sulfanoric; ((2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)(pyridin-2-yl)-′/.
  • 6 -sulfanone ((4-fluorophenyl)imino(methyl)(4-(5-(trifluromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/. 6 -sulfanone; ((4-methoxyphenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/. 6 -sulfanone; ((5-methoxypyridin-2-yl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.
  • 6 -sulfanone (2-(dimethylamino)ethyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′/.
  • 6 -sulfanone (2-(dimethylamino)ethyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/.
  • 6 -sulfanone (2-fluorobenzyl)((2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)-′/. 6 -sulfanone; (2-fluorobenzyl)((3-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)-′/.
  • 6 -sulfanone (2-fluorobenzyl)(isopropyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-′/. 6 -sulfanone; (2-fluorobenzyl)(methyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)imino)-′/.
  • 6 -sulfanone (4-fluorophenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′/. 6 -sulfanone; (4-methoxyphenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′/. 6 -sulfanone; (4-methoxyphenyl)(methyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)imino)-′/.
  • 6 -sulfanone (cyclobutylmethyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′/. 6 -sulfanone; (cyclobutylmethyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/. 6 -sulfanone; (cyclohexyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.
  • 6 -sulfanone (cyclopentyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/. 6 -sulfanone; (cyclopentyl)methyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′/. 6 -sulfanone; (cyclopentylmethyl)(methyl)((4-(5-(trifluoromethyl 1,2,4-oxadiazol-3-yl)benzyl)imino)-′/.
  • 6 -sulfanone (cyclopropylimino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/. 6 -sulfanone; (cyclopropylmethyl)(2-fluorobenzyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-′/. 6 -sulfanone; (cyclopropylmethyl)(2-(trifluorophenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-′/.
  • the present invention also relates to intermediates useful in the preparation of the compounds of Formula I.
  • Such intermediates include but are not limited to 1a and 1b;
  • L 1 , A, L 2 , R 10 are as defined herein before.
  • the present invention relates to a process for preparing the compound claimed in claim 1 .
  • the process of the present invention comprises one or more steps selected from a to p depending upon the definition of L 2 .
  • step (a) a compound of formula 1 is esterified into a compound of formula 2 using suitable esterifying reactant and reagent:
  • step (b) the compound of formula 2 by reacting with hydroxyl amine hydrochloride in the presence of suitable base is converted into a compound of formula 3 or the compound of formula 1 by reacting with hydroxyl amine is converted into a compound of formula 3′:
  • step (c) the compound of formula 3 and a compound of formula 8 are cyclized to obtain a compound of formula 4 or the compound of formula 3′ and a compound of formula 8 are cyclized to obtain a compound of formula 5:
  • step (d) the compound of formula 4 is hydrolyzed into a compound of formula 5:
  • step (e) the compound of formula 5 and a compound of formula 6 are reacted to obtain the compound of formula I:
  • step (f) a compound of formula 6 is reacted with a compound of formula 7 to obtain a compound of formula 1a:
  • step (g) the compound of formula 1a by reacting with hydroxyl amine hydrochloride is converted into a compound of formula 1b:
  • step (h) the compound of formula 1b and a compound of formula 8 are cyclized to obtain a compound of formula I:
  • step (i) a compound of formula 9 is reacted with ammonium carbamate to obtain a compound of formula 10:
  • step (j) the compound of formula 10 is reacted with a compound of formula 11 to obtain a compound of formula 1a:
  • step (k) the compound of formula 1a is reacted with hydroxyl amine hydrochloride to obtain a compound of formula 1b:
  • step (l) the compound of formula 1b and the compound of formula 8 are cyclized to obtain the compound of formula I:
  • step (m) the compound of formula 9 is imidized to obtain a compound of formula 11:
  • step (n) the compound of formula 11 is cyclized with the compound of formula 8 to obtain a compound of formula 12:
  • step (o) the compound of formula 12 is reacted with ammonium carbamate to obtain a compound of formula 13:
  • step (p) the compound of formula 13 is reacted with a compound of formula 14 to obtain the compound of formula I:
  • Compound/s of the present invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the compound/s of the present invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.
  • An anion part of the salt in case the compound/s of Formula I is a cationic or capable of forming a cation can be inorganic or organic.
  • a cation part of the salt in case the compound/s of Formula I is an anionic or capable of forming anion can be inorganic or organic.
  • examples of inorganic anion part of the salt include but are not limited to chloride, bromide, iodide, fluoride, sulfate, phosphate, nitrate, nitrite, hydrogen carbonates, hydrogen sulfate.
  • organic anion part of the salt examples include but are not limited to formate, alkanoates, carbonates, acetates, trifluoroacetate, trichloroacetate, propionate, glycolate, thiocyanate, lactate, succinate, malate, citrates, benzoates, cinnamates, oxalates, alkylsulphates, alkylsulphonates, arylsulphonates aryldisulphonates, alkylphosphonates, arylphosphonates, aryldiphosphonates, p-toluenesulphonate, and salicylate.
  • inorganic cation part of the salt examples include but are not limited to alkali and alkaline earth metals.
  • organic cation part of the salt examples include but are not limited to pyridine, methyl amine, imidazole, benzimidazole, hitidine, phosphazene, tetramethyl ammonium, tetrabutylammonium, choline and trimethylamine.
  • Metal ions in metal complexes of the compound/s of Formula I are especially the ions of the elements of the second main group, especially calcium and magnesium, of the third and fourth main group, especially aluminium, tin and lead, and also of the first to eighth transition groups, especially chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Particular preference is given to the metal ions of the elements of the fourth period and the first to eighth transition groups.
  • the metals can be present in the various valencies that they can assume.
  • Compound/s selected from Formula I typically may exist in more than one form.
  • Formula I thus includes all crystalline and non-crystalline forms of the compound/s that Formula I represents.
  • Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts.
  • Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types).
  • polymorph refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice.
  • polymorphs can have the same chemical composition, they can also differ in composition due to the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability.
  • a polymorph of a compound represented by Formula I can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound represented by Formula I.
  • Preparation and isolation of a particular polymorph of a compound represented by Formula I can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.
  • the present invention relates to a composition
  • a composition comprising the compound/s of Formula I agriculturally acceptable salts, metal complexes, constitutional isomers, stereo-isomers, diastereoisomers, enantiomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, geometric isomers, or N-oxides thereof optionally with one or more additional active ingredient with the auxiliary such as inert carrier or any other essential ingredient such as surfactants, additives, solid diluents and liquid diluents.
  • the compound/s of Formula I and the compositions according to the invention, respectively, are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.
  • the compound/s of Formula I and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g.
  • the present invention also includes a composition comprising at least one compound of Formula I and seed.
  • the amount of the compound/s of Formula I in the composition ranges from 0.1 gai (gram per active ingredient) to 10 kgai (kilogram per active ingredient) per 100 kg of seeds.
  • compound/s of Formula I and compositions thereof, respectively are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • field crops such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant propagation material is to be understood to denote all the generative or reproductive parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (c. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts, twigs, flowers, and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil.
  • These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
  • treatment of plant propagation materials with compound/s of Formula I and compositions thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
  • cultiva plants is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://cera-gmc.org/, see GM crop database therein).
  • Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g.
  • auxin herbicides such as dicamba or 2,4-D
  • bleacher herbicides such as hydroxylphenylpyruvate dioxygena
  • herbicides e. bromoxynil or ioxynil herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, IIPPD inhibitors, auxin herbicides, or ACCase inhibitors.
  • These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci.
  • mutagenesis e.g. Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g. tribenuron.
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus , particularly from Bacillus thuringiensis , such as ⁇ -endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CrylIA(b), CrylIIA, CrylIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp.
  • VIP1 vegetative insecticidal proteins
  • 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
  • these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO02/015701).
  • Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP374753, WO93/007278, WO95/34656, EP427 529, EP451 878, WO03/18810 and WO03/52073.
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.
  • insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).
  • Genetically modified plants capable to synthesize one or more insecticidal proteins are, e.
  • WO 03/018810 MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bbl toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cryl F toxin and PAT enzyme).
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens.
  • proteins are the so-called “pathogenesis-related proteins”
  • PR proteins see, e. g. EP392225
  • plant disease resistance genes e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solanum bulbocastanum
  • T4-lysozym e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • productivity e. g. bio mass production, grain yield, starch content, oil content or protein content
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape, DOW Agro Sciences, Canada).
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany).
  • a modified amount of substances of content or new substances of content specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany).
  • the present invention also relates to a method for controlling or preventing infestation of plants by phytopathogenic micro-organisms in agricultural crops and or horticultural crops wherein an effective amount of at least one compound of formula I or the combination of the present invention or the composition of the present invention, is applied to the seeds of plants.
  • the compound/s, combination/s and composition/s of the present invention can be used for controlling or preventing plant diseases.
  • the compound/s of Formula I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:
  • Albugo spp. white rust on ornamentals, vegetables (e. g. A. candida ) and sunflowers (e. g. A. tragopogonis ); Altemaria spp. ( Alternaria leaf spot) on vegetables, rape ( A. brassicola or brassicae ), sugar beets ( A. tenuis ), fruits, rice, soybeans, potatoes (e. g. A. solani or A. alternata ), tomatoes (e. g. A. solani or A. alternata ) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A.
  • tritici anthracnose
  • Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight ( D. maydis ) or Northern leaf blight ( B. zeicola ) on corn, e. g. spot blotch (6. sorokiniana ) on cereals and e. g. B. oryzae on rice and turfs
  • Blumeria (formerly Erysiphe ) graminis (powdery mildew) on cereals (e. g.
  • Botrytis cinerea (teleomorph: Botryotinia fuceliana : grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma ) spp. (rot or wilt) on broad-leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. ( Cercospora leaf spots) on corn (e. g.
  • Gray leaf spot C. zeae - maydis ), rice, sugar beets (e. g. C. beticola ), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii ) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum : leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris ) spp. (leaf spots) on corn ( C. carbonum ), cereals (e. g.
  • C. sativus anamorph: B. sorokiniana
  • rice e. g. C. miyabeanus , anamorph: H. oryzae
  • Colletotrichum teleomorph: Glomerella
  • spp. anthracnose on cotton (e. g. C. gossypii ), corn (e. g. C. graminicola : Anthracnose stalk rot), soft fruits, potatoes (e. g. C. coccodes : black dot), beans (e. g. C. lindemuthianum ) and soybeans (e. g. C. truncatum or C.
  • Corticium spp. e. g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cycloconium spp., e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C.
  • liriodendri teleomorph: Neonectria liriodendri : Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia ) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D. phaseolorum (damping off) on soybeans; Drechslera (syn. Helminthosporium , teleomorph: Pyrenophora ) spp. on corn, cereals, such as barley (e. g. D. teres , net blotch) and wheat (e. g. D. D.
  • tritici - repentis tritici - repentis : tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus ) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum ), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (£. pyri ), soft fruits (£. veneta : anthracnose) and vines (£.
  • ampelina anthracnose
  • Entyloma oryzae leaf smut
  • Epicoccum spp. black mold
  • Erysiphe spp. potowdery mildew
  • sugar beets £. betae
  • vegetables e. g. E. pisi
  • cucurbits e. g. E. cichoracearum
  • cabbages e. g. E. cruciferarum
  • Eutypa lata Eutypa canker or diehack , anamorph: Cytosporina lata , syn.
  • Microsphaera diffusa (powdery mildew) on soybeans
  • Monilinia spp. e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants
  • Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch ) on wheat or M. fijiensis (black Sigatoka disease) on bananas
  • Peronospora spp. downy mildew) on cabbage (e. g. P.
  • brassicae ), rape (e. g. P. parasitica ), onions (e. g. P. destructor ), tobacco ( P. tabacina ) and soybeans (e. g. P. manshurica ); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e. g. on vines (e. g. P. tracheiphila and P. tetraspora ) and soybeans (e. g. P. gregata : stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P.
  • rape e. g. P. parasitica
  • onions e. g. P. destructor
  • tobacco P. tabacina
  • soybeans e. g. P. manshurica
  • betae root rot, leaf spot and damping-off on sugar beets
  • Phomopsis spp. on sunflowers, vines (e. g. P. viticola : can and leaf spot)
  • soybeans e. g. stem rot: P. phaseoli , teleomorph: Diaporthe phaseolorum
  • Physoderma maydis brown spots
  • Phytophthora spp. wilt, root, leaf, fruit and stem root
  • various plants such as paprika and cucurbits (e. g. P. capsici ), soybeans (e. g. P. megasperma , syn. P. sojae ), soybeans, potatoes and tomatoes (e. g.
  • P. infestans late blight
  • broad-leaved trees e. g. P. ramorum : sudden oak death
  • Plasmodiophora brassicae club root
  • Plasmopara spp. e. g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers
  • Podosphaera spp. powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples
  • Polymyxa spp. e. g. on cereals, such as barley and wheat ( P.
  • Pseudocercosporella herpotrichoides eyespot, teleomorph: Tapesia yallundae ) on cereals, e. g. wheat or barley
  • Pseudoperonospora downy mildew
  • Pseudopezicula tracheiphila red fire disease or .rotbrenner ’, anamorph: Phialophora ) on vines
  • Puccinia spp. rusts
  • P. oryzae (teleomorph: Magnaporthe grisea , rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum ); Ramularia spp., e. g. R. collo - cygni ( Ramularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp.
  • R. solani root and stem rot
  • S. solani silk and stem rot
  • S. solani silk and stem rot
  • S. solani silk blight
  • rice or R. cerealis Rhizoctonia spring blight
  • Rhizopus stolonifer black mold, soft rot
  • strawberries carrots, cabbage, vines and tomatoes
  • Rhynchosporium secalis scald
  • Sarocladium oryzae and S. attenuatum sheath rot) on rice
  • Sclerotinia spp Sclerotinia spp.
  • seed rot or white mold on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum ) and soybeans (e. g. S. rolfsii or S. sclerotiorum ); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici ( Septoria blotch) on wheat and S. (syn. Stagonospora ) nodorum ( Stagonospora blotch) on cereals; Uncinula (syn.
  • Erysiphe ) necator prowdery mildew, anamorph: Oidium tuckeri ) on vines
  • Setospaeria spp. leaf blight
  • corn e. g. S. turcicum , syn. Helminthosporium turcicum
  • turf e. g. S. turcicum , syn. Helminthosporium turcicum
  • Sphaerotheca fuliginea prowdery mildew
  • Spongospora subterranea powdery scab
  • the compounds of formula I, the combinations or the compositions thereof may be used to treat several fungal pathogens.
  • pathogens of fungal diseases which can be treated in accordance with the invention include:
  • Ustilaginales such as Ustilaginoidect vireos, Ustilago nuda, Ustilago tritici, Ustilago zeae , rusts for example those caused by Pucciniales such as Cerotelium fid, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp. Hordei, Puccinia striiformis f.sp.
  • Pucciniales such as Cerotelium fid, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia
  • Secalis, Pucciniastrum coryli , or Uredinales such as Cronartium ribicola, Gymnosporangium juniperi - viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor and Uromyces viciae - fabae ; and other rots and diseases such as those caused by Cryptococcus spp., Exobasidium vexans, Marasrniellus inoderma, Mycena spp., Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani, Thanetephorus cucurnzeris, Entyl
  • diseases caused by rust disease pathogens for example Gymnospomngium species, for example Gymnospomngium sabinae, Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae ⁇ Puccinia species, for example Puccinia recondita, Puccinia graminis oder Puccinia strif ormis; Uromyces species, for example Uromyces appendiculatus;
  • Cronartium ribicola White pine blister rust
  • Gymnospomngium juniperi - virginianae Cedar-apple rust
  • Hemileia vastatrix Coffee rust
  • Phakopsora meibomiae and P. pachyrhizi Soybean rust
  • Puccinia coronata Crown Rust of Oats and Ryegrass
  • Puccinia graminis Stetem rust of wheat and Kentucky bluegrass, or black rust of cereals
  • Puccinia hemerocallidis Daylily rust
  • Puccinia persistens subsp.
  • Puccinia sorghi rust in corn
  • Puccinia strilformis ‘Yellow rust’ in cereals
  • Uromyces appendiculatus rust of beans
  • Uromyces phaseoli Bean rust
  • Puccinia melanocephata ‘Brown rust’ in sugarcane
  • Puccinia kuehnii ‘Orange rust’ in sugarcane
  • Plants which can be treated in accordance with the invention include the following: cotton, flax, grapevine, fruits, vegetables, such as Rosaceae sp (for example pome fruits such as apples, pears, apricots, cherries, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example banana trees and plantations), Rubiaceae sp.
  • Rosaceae sp for example pome fruits such as apples, pears, apricots, cherries, almonds and peaches
  • Ribesioidae sp. Juglandaceae sp.
  • Betulaceae sp. Ana
  • Theaceae sp. for example coffee
  • Theaceae sp. Sterculiceae sp.
  • Rutaceae sp. for example lemons, oranges and grapefruit
  • Vitaceae sp. for example grapes
  • Solanaceae sp. for example tomatoes, peppers
  • Liljaceae sp. for example lettuce
  • Umbelliferae sp. for example lettuce
  • Umbelliferae sp. for example Cruciferae sp.
  • Chenopodiaceae sp. Cucurbitaceae sp.
  • Cucurbitaceae sp. for example cucumber
  • Alliaceae sp. for example leek, onion
  • peas for example peas
  • major crop plants such as Poaceae/Gramineae sp.
  • Poaceae/Gramineae sp. for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale
  • Asteraceae sp. for example sunflower
  • Brassicaceae sp. for example white cabbage, red cabbage, broccoli, cauliflower, Bmssels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress
  • Fabacae sp. for example bean, peanuts
  • Papilionaceae sp. for example soya bean
  • the present invention also relates to the use of compounds of formula 1, the combinations or the compositions thereof for controlling or preventing the following plant diseases: Puccinia spp. (rusts) on various plants, for example, but not limited to P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye and Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhizi and P.
  • Puccinia spp. rusts
  • rusts rusts
  • P. triticina brown or leaf rust
  • P. striiformis stripe or yellow rust
  • P. hordei dwarf rust
  • the present invention further relates to the use of compounds of formula I, the combinations or the compositions thereof for controlling or preventing against phytopathogenic fungi such as Phakopsora pachyrhizi, Phakopsora meibomiae , of agricultural crops and or horticultural crops.
  • the compounds of Formula I, the combinations and the compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials.
  • the term “protection of materials” is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria.
  • Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichuras spp.; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Porl′a spp., Serpula spp.
  • yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.
  • the compound/s of Formula I, the combinations and the compositions thereof, respectively, are particularly suitable for controlling the following plant diseases: Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.
  • the present invention further relates to a method for controlling or preventing phytopathogenic fungi.
  • the method comprises treating the fungi or the materials, plants, plant parts, locus thereof, soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of Formula I or the combinations or the compositions comprising at least one compound of Formula I.
  • the method of treatment according to the invention can also be used in the field of protecting stored products or harvest against attack of fungi and microorganisms.
  • the term “stored products” is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired.
  • Stored products of crop plant origin such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted, which process is also known as post-harvest treatment.
  • stored products are timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood.
  • Stored products of animal origin are hides, leather, furs, hairs and the like.
  • the combinations according the present invention can prevent disadvantageous effects such as decay, discoloration or mold.
  • stored products is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.
  • the compound/s of Formula I, the combinations and the compositions thereof, respectively, may be used for improving the health of a plant.
  • the invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of compound/s I and compositions thereof, respectively.
  • plant health is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves (“greening effect”)), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress.
  • yield e. g. increased biomass and/or increased content of valuable ingredients
  • plant vigor e. g. improved plant growth and/or greener leaves (“greening effect”)
  • quality e. g. improved content or composition of certain ingredients
  • tolerance to abiotic and/or biotic stress e. g. improved content or composition of certain ingredients
  • the compound/s of Formula I can be present in different crystal modifications or polymorphs whose biological activity may differ. They are likewise subject matter of the present invention.
  • the compound/s of Formula I are employed as such or in the form of compositions for treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances.
  • the application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.
  • Plant propagation materials may be treated with compound/s of Formula I, the combinations and the compositions thereof protectively either at or before planting or transplanting.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of Formula I.
  • An agrochemical composition comprises a fungicidally effective amount of a compound of Formula I.
  • effective amount denotes an amount of the composition or of the compound/s of Formula I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound of Formula I used.
  • compositions e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • composition types are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes, pastilles, wettable powders or dusts (e. g.
  • compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e. g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e. g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e. g. cyclohexanone; esters, e. g.
  • mineral oil fractions of medium to high boiling point e. g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydronaphthalene, al
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e. g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e. g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates.
  • Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates,N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.
  • Suitable cationic surfactants are quaternary surfactants, for ex ample quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines.
  • Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compounds of Formula I on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (c. g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water-soluble dyes.
  • examples are inorganic colorants (c. g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e. g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • composition types and their preparation are:
  • a compound of Formula I and 5-15 wt % wetting agent e. g. alcohol alkoxylates
  • a water-soluble solvent e. g. alcohols
  • a compound of Formula I and 1-10 wt % dispersant e. g. polyvinyl pyrrolidone
  • organic solvent c. g. cyclohexanone
  • emulsifiers e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent c. g. aromatic hydrocarbon
  • Emulsions (EW, EO, ES)
  • emulsifiers c. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • 20-40 wt % water-insoluble organic solvent e. g. aromatic hydrocarbon
  • a compound of Formula I In an agitated ball mill, 20-60 wt % of a compound of Formula I are comminuted with addition of 2-10 wt % dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate), 0.1-2 wt % thickener (e. g. xanthan gum) and water ad 100 wt % to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt % hinder (e. g. polyvinyl alcohol) is added.
  • dispersants and wetting agents e. g. sodium lignosulfonate and alcohol ethoxylate
  • 0.1-2 wt % thickener e. g. xanthan gum
  • 50-80 wt % of a compound of Formula I are ground finely with addition of dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt % and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants and wetting agents e. g. sodium lignosulfonate and alcohol ethoxylate
  • sodium lignosulfonate 1-3 wt % wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g. silica gel) ad 100 wt %. Dilution with water gives a stable dispersion or solution of the active substance.
  • wetting agents e. g. alcohol ethoxylate
  • solid carrier e. g. silica gel
  • a compound of Formula I In an agitated ball mill, 5-25 wt % of a compound of Formula I are comminuted with addition of 3-10 wt % dispersants (e. g. sodium lignosulfonate), 1-5 wt % thickener (e. g. carboxymethyl cellulose) and water ad 100 wt % to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e. g. sodium lignosulfonate
  • 1-5 wt % thickener e. g. carboxymethyl cellulose
  • 5-20 wt % of a compound of Formula I are added to 5-30 wt % organic solvent blend (e. g. fatty acid dimethyl amide and cyclohexanone), 10-25 wt % surfactant blend (e. g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100%. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
  • organic solvent blend e. g. fatty acid dimethyl amide and cyclohexanone
  • surfactant blend e. g. alcohol ethoxylate and arylphenol ethoxylate
  • An oil phase comprising 5-50 wt % of a compound of Formula I, 0-40 wt % water insoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt % acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt % of a compound of Formula I according to the invention, 0-40 wt % water insoluble organic solvent (e. g.
  • an isocyanate monomer c. g. diphenylmethene-4,4′-diisocyanatae
  • a protective colloid e. g. polyvinyl alcohol
  • the addition of a poly amine results in the formation of polyurea microcapsules.
  • the monomers amount to 1-10 wt %.
  • the wt % relate to the total CS composition.
  • 1-10 wt % of a compound of Formula 1 are ground finely and mixed intimately with solid carrier (e. g. finely divided kaolin) ad 100 wt %.
  • solid carrier e. g. finely divided kaolin
  • 0.5-30 wt % of a compound of Formula I are ground finely and associated with solid carrier (e. g. silicate) ad 100 wt %.
  • Solid carrier e. g. silicate
  • Granulation is achieved by extrusion, spray-drying or fluidized bed.
  • organic solvent e. g. aromatic hydrocarbon
  • compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt % anti-freezing agents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt % colorants.
  • auxiliaries such as 0.1-1 wt % bactericides, 5-15 wt % anti-freezing agents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt % colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active ingredient (ai).
  • the active ingredients (ai) are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations.
  • Methods for applying compound/s of Formula 1, the combinations and the compositions thereof, respectively, onto plant propagation material, especially seeds include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods.
  • compound/s of Formula I, the combinations and the compositions thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 1.0 kg per ha, and in particular from 0.1 to 1.0 kg per ha.
  • amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
  • the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:20 to 20:1.
  • a pesticide is generally a chemical or biological agent (such as pesticidally active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests.
  • Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease.
  • pesticide includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.
  • the user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful arca.
  • composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
  • a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
  • one embodiment of the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component 3) as defined herein.
  • the compound/s of Formula I, the combinations and the compositions thereof comprising them in the use as fungicides with other fungicides may result in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance development. Furthermore, in many cases, extraordinary effects are obtained.
  • the present invention also relates to the combination comprising at least one compound of Formula T and at least one further pesticidally active substance selected from the group of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertiliers and nutrients.
  • the pesticidally active substances reported in WO2015 185485 pages 36-43 and WO2017093019 pages 42-56 can be used in conjunction with which the compound/s of Formula I.
  • component 2 The active substances referred to as component 2, their preparation and their activity e. g. against harmful fungi is known (cf: http://www.alanwood.net/pesticides/); these substances are commercially available.
  • the compounds described by 1U PAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP141317; EP152031; EP226917; EP243970; EP256503; EP428941; EP532022; EP1028125; EP1035122; EP1201648; EP1122244, JP20023 16902; DE19650197; DE10021412; DE102005009458; U.S. Pat. Nos.
  • the present invention furthermore relates to agrochemical mixtures comprising at least one compound of Formula I (component 1) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier.
  • agrochemical mixtures comprising at least one compound of Formula I (component 1) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier.
  • the order of application is not essential for working of the present invention.
  • the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day.
  • the weight ratio of the component 1) and the component 2) generally depends from the properties of the active components used, usually it is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1, even more preferably in the range of 1:4 to 4:1 and in particular in the range of 1:2 to 2:1.
  • the weight ratio of the component 1) and the component 2) usually is in the range of 1000:1 to 1:1000, often in the range of 100:1 to 1:100, regularly in the range of 50:1 to 1:50, preferably in the range of 20:1 to 1:20, more preferably in the range of 10:1 to 1:10, even more preferably in the range of 4:1 to 1:4 and in particular in the range of 2:1 to 1:2.
  • the weight ratio of component 1) and component 2) depends from the properties of the active substances used, usually it is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1 and in particular in the range of 1:4 to 4:1, and the weight ratio of component 1) and component 3) usually it is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1 and in particular in the range of 1:4 to 4:1.
  • any further active components are, if desired, added in a ratio of 20:1 to 1:20 to the component 1).
  • the present invention also relates to a process for preparing the compound/s of the present invention.
  • the process for preparing the compound/s of the present invention is described in the experimental section in more detail.
  • Step 4 4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid
  • Step-6 (2-Fluorophenyl)(imino)(methyl)-X 6 -sulfanone
  • Step 7 Preparation of N-((2-fluorophenyl)(methyl)(oxo)-/. 6 -sulfanylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide (Compound 3)
  • Example-2 2-fluorophenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-/. 6 -sulfanone (Compound 12)
  • Step 1 4-(((2-Fluorophenyl)(methyl)(oxo)-X 6 -sulfanylidene)amino)benzonitrile
  • Step 2 4-(((2-Fluorophenyl)(methyl)(oxo)-X 6 -sulfanylidene)amino)-N′-hydroxybenzimidamide
  • Step 3 (2-Fluorophenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)- ⁇ 6 -sulfanone
  • the crude product was purified by column chromatography on silica gel using eluent hexane to 40% Ethyl acetate in hexane to obtain pure (2-fluorophenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyMmino)-L 6 -sulfanone (0.4 g, 60% yield).
  • Step 1 4-((((2-Fluorophenyl)(methyl)(oxo)-I 6 -sulfanylidene)amino)methyl)benzonitrile
  • Step 2 (Z)-4-((((2-Fluorophenyl)(methyl)(oxo)-/. 6 -sulfanylidene)amino)methyl)-N′-hydroxybenzimidamide
  • Step 3 (2-fluorophenyl)(methyl)(0-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino))-2-sulfanone
  • Step-2 —N-((2-fluorophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide (Compound No. 155)
  • Example 5 Preparation of ((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(2-fluorophenyl)(methyl) ⁇ circumflex over ( ) ⁇ 5 -sulfanone (Compound No. 165)
  • Step 1 —3-Fluoro-4-(((2-fluorophenyl)(methyl)(oxo)-X 6 -sulfaneylidene)amino)benzonitrile
  • the obtained crude product was purified by flash column chromatography on silica gel using hexane to 50% ethyl acetate in hexane as an eluent to obtain pure 3-fluoro-4-(((2-fluorophenyl)(methyl)(oxo)-) ⁇ 6 -sulfanylidene)amino)benzonitrile (0.5 g, 1 6 mmol, 71% yield).
  • Step 2 —3-Iduoro-4-(((2-fluorophenyl)(methyl)(oxo)-/. 6 -sulfanylidene)amino)-N′-hydroxybenzimidamide
  • N′-hydroxy-4-(methylthio)benzimidamide (10.1 g) was prepared by the procedure described in step 2 of example 1.
  • Step 2 —3-(4-(methylthio)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole
  • Step 3 Synthesis of imino(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X 6 -sulfanone
  • Step 4 —Synthesis of 2-fluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yllphenyll-X ⁇ circumflex over ( ) ⁇ -sulfaneylidenelbenzamide
  • Example 7 Preparation of ((3-chlorobenzyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)- ⁇ 6 -sulfanone (Compound No. 182)
  • Step 1 —4-(S-methylsulfonimidoyl)benzonitrile
  • Step 2 —4-(N-(3-chlorobenzyl)-S-methylsulfonimidoyl)benzonitrile
  • Step 3 —4-(N-(3-chlorobenzyl)-S-methylsulfonimidoyl)-N′-hydroxybenzimidamide
  • Step 4 —((3-chlorobenzyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-L 6 -sulfanone
  • Example 8 Preparation of 3N-((4-fluorophenyl)(methyl)(oxo)-X 6 -sulfaneylidene)-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide (Compound No. 186)
  • Step-1 —2-(4-(N′-hydroxycarbamimidoyl)phenyl)acetic acid
  • Step-2 Preparation of 2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid
  • reaction mixture was concentrated and purified by column chromatography on silica gel using hexane to 60% ethyl acetate in hexane as an eluent to obtain pure 2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid (6.0 g, 78% yield).
  • Step-3 Preparation of N-((4-fluorophenyl)(methyl)(oxo)-/. 6 -sulfaneylidene)-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide
  • Example 9 Preparation of N42-fluorophenyl)(methyl)(oxo)-4 6 -sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)picolinamide
  • Step 1 Synthesis of 5-(N′-hydroxycarbamimidoyl)picolinic acid
  • Step 2 —5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)picolinic acid
  • Step 3 Synthesis of N-((2-fluorophenyl)(methyl)(oxo)-L 5 -sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)picolin amide
  • N-((2-fluorophenyl)(methyl)(oxo)-X 6 -sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)picolinamide (0.13 g, 23% yield) was synthesized by the procedure as described in step-3 of example 8.
  • Step 1 Preparation of methyl-4-(2-amino-2-(hydroxyimino)ethyl)benzoate
  • Step 2 Preparation of methyl 4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzoate
  • Step-3 —N-(methyl(oxo)(phenyl)-X 6 -sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide (compound no. 222)
  • Example 1 Pyricularia oryme (Rice Blast)
  • a visual assessment of compound's performance was carried out by rating the disease severity (0-100% scale) on treated plants on 3, 7, 10 & 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated control. The sprayed plants were also assessed for compound's plant compatibility by recording symptoms like necrosis, chlorosis & stunting.

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Abstract

The present invention relates to novel oxadiazoles of Formula I.wherein, R1, L1, A, L2 and R10 are as defined in the detailed description.

Description

    FIELD OF THE INVENTION
  • The present invention relates to novel oxadiazoles, N-oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof and plurality of processes for preparing the same. Further, the present invention relates to a combination and a composition comprising novel oxadiazoles of the present invention. Still further, the present invention relates to a use of novel oxadiazoles of the present invention for controlling or preventing phytopathogenic fungi and to a method for controlling or preventing phytopathogenic harmful fungi.
    • BACKGROUND
  • Oxadiazoles have already been disclosed in the literature. For example in JP56065881, JP63 162680, JPS6061573, JPS6296480, JPS6051188, JP2005336101, WO2005051932, EP3165093, EP3165094, EP3167716, EP3165093, JP2017190296, U.S. Pat. No. 4,488,897, WO2015185485, WO2017055469, WO2017055473, WO2017076739, WO20 17076740, WO2017081311, WO2017085098, WO20 17085 100, WO2017093019, WO2017093348, WO20 17 102006, WO2017103219, WO2017 103223, WO20 17109044, WO2017 110861, WO20171 10862, WO20171 10863, WO2017 110864, WO20171 10865, WO20171 11152, WO20171 18689, WO2017148797, WO2017 157962, WO2017162868, WO2017169893, WO2017174158, WO2017 178549, WO2017 198852, WO2017207757, WO20 17211649, WO2017211650, WO2017211652, WO2017213252, WO2017220485, WO201772247, WO201776742, WO201776757, WO201776935, WO201781309, WO201781310, WO201781312, WO2018015447, WO2018015449, WO2018015458, WO20 18029242, WO20 18030460, WO20 18056340, WO20 18055 135, WO2018065414, WO201 8080859, WO2018118781, WO20181 17034, WO20181 14393, WO2018 153730, WO2018158365, WO20 18162643, WO2018 184970, WO2018 184982, WO2018 184984, WO2018184985, WO2018184986, WO2018184987, WO2018 184988, WO2018185013, WO2018185211, WO2018187553 and WO2018202491 various oxadiazoles have be disclosed.
  • The oxadiazole compounds reported in the above literature have disadvantages in certain aspects, such as that they exhibit a narrow spectrum of application or they do not have satisfactory fungicidal activity, particularly at low application rates.
  • Therefore, it is an object of the present invention to provide compound/s having improved/enhanced activity and/or a broader activity spectrum against phytopathogenic fungi.
  • This objective is achieved by the using oxadiazoles of the present invention for controlling or preventing phytopathogenic fungi.
    • SUMMARY
  • The present invention relates to novel oxadiazoles of Formula I.
  • Figure US20220169621A1-20220602-C00002
  • wherein, R1, L1, A, L2 and R10 are as defined in the detailed description.
  • The compounds of formula I have now been found to be advantages over the compounds reported in the literature in either of improved fungicidal activity, broader spectrum biological activity, lower application rates, biological or environmental properties, or enhanced plant compatibility.
  • The present invention further relates to a combination comprising novel oxadizoles of the present invention and at least one further pesticidally active substance for effectively controlling or preventing phytopathogenic fungi which are difficult to control or prevent.
  • The present invention still further relates to a composition comprising novel oxadizoles or novel oxadiazoles in combination with further pesticidally active substance.
  • The present invention still further relates to a method and use of novel oxadizoles, combinations or compositions thereof for controlling and or preventing plant diseases, particularly phytopathogenic fungi.
    • DETAILED DESCRIPTION OF THE INVENTION Definitions
  • The definitions provided herein for the terminologies used in the present disclosure are for illustrative purpose only and in no manner limit the scope of the present invention disclosed in the present disclosure.
  • As used herein, the terms “comprises”, “comprising”, “includes”, “including”, “has”, “having”, “contains”, “containing”, “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.
  • The transitional phrase “consisting of” excludes any element, step or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase “consisting of” appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.
  • The transitional phrase “consisting essentially of” is used to define a composition or method that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term “consisting essentially of” occupies a middle ground between “comprising” and “consisting of”.
  • Further, unless expressly stated to the contrary, “or” refers to an inclusive “or” and not to an exclusive “or”. For example, a condition A “or” B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
  • Also, the indefinite articles “a” and “an” preceding an element or component of the present invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.
  • As referred to in this disclosure, the term “invertebrate pest” includes arthropods, gastropods and nematodes of economic importance as pests. The term “arthropod” includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs and symphylans. The term “gastropod” includes snails, slugs and other Stylommatophora. The term “nematode” refers to a living organism of the Phylum Nematoda. The term “helminths” includes roundworms, heartworms, phytophagous nematodes (Nematoda), flukes (Tematoda), acanthocephala and tapeworms (Cestoda).
  • In the context of this disclosure “invertebrate pest control” means inhibition of invertebrate pest development (including mortality, feeding reduction, and/or mating disruption), and related expressions are defined analogously.
  • The term “agronomic” refers to the production of field crops such as for food and fiber and includes the growth of corn, soybeans and other legumes, rice, cereal (e.g., wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).
  • The term “nonagronomic” refers to other than field crops, such as horticultural crops (e.g., greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial and industrial structures, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), wood products, stored product, agro-forestry and vegetation management, public health (i.e. human) and animal health (e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife) applications.
  • Nonagronomic applications include protecting an animal from an invertebrate parasitic pest by administering a parasiticidally effective (i.e. biologically effective) amount of a compound of the present invention, typically in the form of a composition formulated for veterinary use, to the animal to be protected. As referred to in the present disclosure and claims, the terms “parasiticidal” and “parasiticidally” refers to observable effects on an invertebrate parasite pest to provide protection of an animal from the pest. Parasiticidal effects typically relate to diminishing the occurrence or activity of the target invertebrate parasitic pest. Such effects on the pest include necrosis, death, retarded growth, diminished mobility or lessened ability to remain on or in the host animal, reduced feeding and inhibition of reproduction. These effects on invertebrate parasite pests provide control (including prevention, reduction or elimination) of parasitic infestation or infection of the animal.
  • The compounds of the present disclosure may be present either in pure form or as mixtures of different possible isomeric forms such as stereoisomers or constitutional isomers. The various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixtures of these isomers fall within the scope of the claims of the present disclosure. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other isomer(s) or when separated from the other isomer(s). Additionally, the person skilled in the art knows processes or methods or technology to separate, enrich, and/or to selectively prepare said isomers.
  • The meaning of various terms used in the description shall now be illustrated.
  • The term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” or —N(alkyl) or alkylcarbonylalkyl or alkylsuphonylamino includes straight-chain or branched Ci to C24 alkyl, preferably Ci to C15 alkyl, more preferably Ci to C10 alkyl, most preferably Ci to C6 alkyl. Non limiting examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1.1.2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl or the different isomers. If the alkyl is at the end of a composite substituent, as, for example, in alkylcycloalkyl, the part of the composite substituent at the start, for example the cycloalkyl, may be mono- or polysubstituted identically or differently and independently by alkyl. The same also applies to composite substituents in which other radicals, for example alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy and the like, are at the end.
  • The term “alkenyl”, used either alone or in compound words includes straight-chain or branched C2 to C24 alkenes, preferably C2 to C15 alkenes, more preferably C2 to C10 alkenes, most preferably C2 to C6 alkenes. Non limiting examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1.2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl and the different isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as a part of a composite substituent, for example haloalkenyl and the like, unless defined specifically elsewhere.
  • Non limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-di methyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, i-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl and the different isomers. This definition also applies to alkynyl as a part of a composite substituent, for example haloalkynyl etc., unless specifically defined elsewhere. The term “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
  • The term “cycloalkyl” means alkyl closed to form a ring. Non limiting examples include cyclopropyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example cycloalkylalkyl etc., unless specifically defined elsewhere.
  • The term “cycloalkenyl” means alkenyl closed to form a ring including monocyclic, partially unsaturated hydrocarbyl groups. Non limiting examples include cyclopropenyl, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as a part of a composite substituent, for example cycloalkenylalkyl etc., unless specifically defined elsewhere.
  • The term “cycloalkynyl” means alkynyl closed to form a ring including monocyclic, partially unsaturated groups. Non limiting examples include cyclopropynyl, cyclopentynyl and cyclohexynyl. This definition also applies to cycloalkynyl as a part of a composite substituent, for example cycloalkynylalkyl etc., unless specifically defined elsewhere.
  • The terms “cycloalkoxy”, “cycloalkenyloxy” and the like are defined analogously. Non limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as a part of a composite substituent, for example cycloalkoxy alkyl etc., unless specifically defined elsewhere.
  • The term “halogen”, either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Non-limiting Examples of “haloalkyl” include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl, and 1,1,1-trifluoroprop-2-yl. This definition also applies to haloalkyl as a part of a composite substituent, for example haloalkylaminoalkyl etc., unless specifically defined elsewhere.
  • The terms “haloalkenyl”, “haloalkynyl” are defined analogously except that, instead of alkyl groups, alkenyl and alkynyl groups are present as a part of the substituent.
  • The term “haloalkoxy” means straight-chain or branched alkoxy groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoroprop-2-oxy. This definition also applies to haloalkoxy as a part of a composite substituent, for example haloalkoxyalkyl etc., unless specifically defined elsewhere.
  • The term “haloalkylthio” means straight-chain or branched alkylthio groups where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above. Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio and 1,1,1-trifluoroprop-2-ylthio. This definition also applies to haloalkylthio as a part of a composite substituent, for example haloalkylthioalkyl etc., unless specifically defined elsewhere.
  • Non limiting examples of “haloalkylsulfinyl” include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O). Examples of “haloalkylsulfonyl” include CF3S(O)2, CCl3S(O)2, CF3CH2S(O)2 and CF3CF2S(O)2.
  • The term “hydroxy” means —OH, Amino means —NRR, wherein R can be H or any possible substituent such as alkyl. Carbonyl means —C(O)—, carbonyloxy means —OC(O)—, sulfinyl means SO, sulfonyl means S(O)2.
  • The term “alkoxy” used either alone or in compound words included Ci to C24 alkoxy, preferably Ci to C15 alkoxy, more preferably Ci to Cio alkoxy, most preferably Ci to C6 alkoxy. Examples of alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy and the different isomers. This definition also applies to alkoxy as a part of a composite substituent, for example haloalkoxy, alkynylalkoxy, etc., unless specifically defined elsewhere.
  • The term “alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2.
  • The term “alkoxyalkoxy” denotes alkoxy substitution on alkoxy.
  • The term “alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio and the different isomers.
  • The terms Halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxylalkyl, and the like, are defined analogously to the above examples.
  • The term “alkylthioalkyl” denotes alkylthio substitution on alkyl. Non limiting examples of “alkylthioalkyl” include —CH2SCH2, —CH2SCH2CH2, CH2CH2SCH2, CH3CH2CH2CH2SCH2 and CH3CH2SCH2CH2. “Alkylthioalkoxy” denotes alkylthio substitution on alkoxy. The term “cycloalkylalkylamino” denotes cycloalkyl substitution on alkyl amino.
  • The terms alkoxyalkoxyalkyl, alkylaminoalkyl, dialkylaminoalkyl, cycloalkylaminoalkyl, cycloalkylaminocarbonyl and the like, are defined analogously to “alkylthioalkyl” or cycloalkylalkylamino.
  • The term “alkoxycarbonyl” is an alkoxy group bonded to a skeleton via a carbonyl group (—CO—). This definition also applies to alkoxycarbonyl as a part of a composite substituent, for example cycloalkylalkoxycarbonyl and the like, unless specifically defined elsewhere.
  • The term “alkoxycarbonylalkylamino” denotes alkoxy carbonyl substitution on alkyl amino. “Alkylcarbonylalkylamino” denotes alkyl carbonyl substitution on alkyl amino. The terms alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl and the like are defined analogously.
  • Non limiting examples of “alkylsulfinyl” include methylsulphinyl, ethylsulphinyl, propylsulphinyl, methylethylsulphinyl, butylsulphinyl, 1-methylpropylsulphinyl, 2-methylpropylsulphinyl, 1,1-dimethylethylsulphinyl, pentylsulphinyl, 1-methylbutylsulphinyl, 2-methylbutylsulphinyl, 3-methylbutylsulphinyl, 2,2-dimethylpropylsulphinyl, 1-ethylpropylsulphinyl, hexylsulphinyl, 1,1-dimethylpropylsulphinyl, 1,2-dimethylpropylsulphinyl, 1-methylpentylsulphinyl, 2-methylpentylsulphinyl, 3-methylpentylsulphinyl, 4-methylpentylsulphinyl, 1,1-dimethylbutylsulphinyl, 1,2-dimethylbutylsulphinyl, 1,3-dimethylbutylsulphinyl, 2,2-dimethylbutylsulphinyl, 2,3-dimethylbutylsulphinyl, 3,3-dimethylbutylsulphinyl, 1-ethylbutylsulphinyl, 2-ethylbutylsulphinyl, 1,1,2-trimethylpropylsulphinyl, 1,2,2-trimethylpropylsulphinyl, 1-ethyl-1-methylpropylsulphinyl and 1-ethyl-2-methylpropylsulphinyl and the different isomers. The term “arylsulfinyl” includes Ar—S(O), wherein Ar can be any carbocycle or heterocycle. This definition also applies to alkylsulphinyl as a part of a composite substituent, for example haloalkylsulphinyl etc., unless specifically defined elsewhere.
  • Non limiting examples of “alkylsulfonyl” include methylsulphonyl, ethylsulphonyl, propylsulphonyl, 1-methyl ethylsulphonyl, butylsulphonyl, 1-methylpropylsulphonyl, 2-methylpropylsulphonyl, 1,1-dimethylethylsulphonyl, pentylsulphonyl, 1-methylbutylsulphonyl, 2-methylbutylsulphonyl, 3-methylbutylsulphonyl, 2,2-dimethylpropylsulphonyl, 1-ethylpropylsulphonyl, hexylsulphonyl, 1,1-dimethylpropylsulphonyl, 1,2-dimethylpropylsulphonyl, 1-methylpentylsulphonyl, 2-methylpentylsulphonyl, 3-methylpentylsulphonyl, 4-methylpentylsulphonyl, 1,1-dimethylbutylsulphonyl, 1,2-dimethylbutylsulphonyl, 1,3-dimethylbutylsulphonyl, 2,2-dimethylbutylsulphonyl, 2,3-dimethylbutylsulphonyl, 3,3-dimethylbutylsulphonyl, 1-ethylbutylsulphonyl, 2-ethylbutylsulphonyl, 1,1,2-trimethylpropylsulphonyl, 1,2,2-trimethylpropylsulphonyl, 1-ethyl-1-methylpropylsulphonyl and 1-ethyl-2-methylpropylsulphonyl and the different isomers. The term “arylsulfonyl” includes Ar—S(O)2, wherein Ar can be any carbocycle or heterocycle. This definition also applies to alkylsulphonyl as a part of a composite substituent, for example alkylsulphonylalkyl etc., unless defined elsewhere.
  • The term “alkylamino”, “dialkylamino”, and the like, are defined analogously to the above examples.
  • The term “carbocycle” includes “aromatic carbocyclic ring system” and “nonaromatic carbocylic ring system” or polycyclic or bicyclic (spiro, fused, bridged, nonfused) ring compounds in which ring may be aromatic or non-aromatic (where aromatic indicates that the Huckel rule is satisfied and non-aromatic indicates that the Huckel rule is not satisfied).
  • The term “hetero” in connection with rings refers to a ring in which at least one ring atom is not carbon and which can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs.
  • The term “heteroaryl” or “aromatic heterocyclic” means 5 or 6-membered, fully unsaturated monocyclic ring system containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur; if the ring contains more than one oxygen atom, they are not directly adjacent; 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulphur or oxygen atom as ring members, for example (but not limited thereto) furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-triazolyl, tetrazolyl; nitrogen-bonded 5-membered heteroaryl containing one to four nitrogen atoms, or benzofused nitrogen-bonded 5-membered heteroaryl containing one to three nitrogen atoms: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms as ring members and in which two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group in which one or two carbon atoms may b e replaced b y nitrogen atoms, where these rings are attached to the skeleton via one of the nitrogen ring members, for example (but not limited to) 1-pyrrolyl, 1-pyrazolyl, 1,2,4-triazol-1-yl, 1-imidazolyl, 1,2,3-triazol-1-yl and 1,3,4-triazol-1-yl.
  • 6-membered heteroaryl which contains one to four nitrogen atoms: 6-membered heteroaryl groups which, in addition to carbon atoms, may contain, respectively, one to three and one to four nitrogen atoms as ring members, for example (but not limited thereto) 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl; benzofused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulphur atom: for example (but not limited to) indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indazol-1-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl, indazol-2-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzo thiophen-6-yl, 1-benzothiophen-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl and 1,3-benzoxazol-7-yl; benzofused 6-membered heteroaryl which contains one to three nitrogen atoms: for example (but not limited to) quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl and isoquinolin-8-yl.
  • This definition also applies to heteroaryl as a part of a composite substituent, for example heteroarylalkyl etc., unless specifically defined elsewhere.
  • The term “aromatic” indicates that the Huckel rule is satisfied and the term “non-aromatic” indicates that the Huckel rule is not satisfied.
  • The term “heterocycle” or “heterocyclic” includes “aromatic heterocycle” or “heteroaryl ring system” and “nonaromatic heterocycle ring system” or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds in which ring may be aromatic or non-aromatic, wherein the heterocycle ring contains at least one heteroatom selected from N, O, S(O)0-2, and or C ring member of the heterocycle may be replaced by C(=0), C(═S), C(═CR*R*) and C═NR*, * indicates integers.
  • The term “non-aromatic heterocycle” or “non-aromatic heterocyclic” means three- to fifteen-membered, preferably three- to twelve-membered, saturated or partially unsaturated heterocycle containing one to four heteroatoms from the group of oxygen, nitrogen and sulphur: mono, bi- or tricyclic heterocycles which contain, in addition to carbon ring members, one to three nitrogen atoms and/or one oxygen or sulphur atom or one or two oxygen and/or sulphur atoms; if the ring contains more than one oxygen atom, they are not directly adjacent; for example (hut not limited to) oxetanyl, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 1-imidazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-1-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-1-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2.4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, pyrrolinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3.4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, pyrazinyl, morpholinyl, thiomorphlinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl, 1,2,4-hexahydrotriazin-3-yl, cycloserines, 2,3,4,5-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 3,4,5,6-tetra-hydro[2H]azepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,4,7-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,6,7-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, hexahydroazepin-1- or -2- or -3- or -4-yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[1H]oxepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,4,7-tetrahydro[1H]oxepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,6,7-tetrahydro[1H]oxepin-2- or -3- or -4- or -5- or -6- or -7-yl, hexahydroazepin-1- or -2- or -3- or -4-yl, tetra- and hexahydro-1,3-diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro-1,4-dioxepinyl. This definition also applies to heterocyclyl as a part of a composite substituent, for example heterocyclylalkyl etc., unless specifically defined elsewhere.
  • The term “trialkylsilyl” includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom such as trimethylsilyl, triethylsilyl and t-butyl-dimethylsilyl. The term “halotrialkylsilyl” denotes at least one of the three alkyl radicals is partially or fully substituted with halogen atoms which may be the same or different. The term “alkoxytrialkylsilyl” denotes at least one of the three alkyl radicals is substituted with one or more alkoxy radicals which may be the same or different. The term “trialkylsilyloxy” denotes a trialkylsilyl moiety attached through oxygen.
  • Non limiting examples of “alkylcarbonyl” include C(O)CH C(O)CH2CH2CH3 and C(O)CH(CH3)2. Examples of “alkoxycarbonyl” include CH3OC(=0), CH3CH2OC(=0), CH3CH2CH2OC(=0), (CH3)2CHOC(=0) and the different butoxy- or pentoxycarbonyl isomers. Examples of “alkylaminocarbonyl” include CH3NHC(=0), CH3CH2NHC(=0), CH3CH2CH2NHC(=0), (CH3)2CHNHC(=0) and the different butylamino- or pentylaminocarbonyl isomers. Non limiting examples of “dialkylaminocarbonyl” include (CH3)2NC(=0), (CH3CH2)2NC(=0), CH3CH2(CH3)NC(=0), CH3CH2CH2(CH3)NC(=0) and (CH3)2CHN(CH3)C(=0). Examples of “alkoxyalkylcarbonyl” include CH3OCH2C(=0), CH3OCH2CH2C(=0), CH3CH2OCH2C(=0), CH3CH2CH2CH2OCH2C(=0) and CH3CH2OCH2CH2C(=0). Non limiting examples of “alkyl thioalkyl carbonyl” include CH3SCH2C(=0), CH3SCH2CH2C(=0), CH3CH2SCH2C(=0), CH3CH2CH2CH2SCH2C(=0) and CH3CH2SCH2CH2C(=0). The term haloalkylsufonylaminocarbonyl, alkylsulfonylaminocarbonyl, alkylthioalkoxycarbonyl, alkoxycarbonylalkyl amino and the like are defined analogously
  • Non limiting examples of “alkylaminoalkylcarbonyl” include CH3NHCH2C(=0), CH3NHCH2CH2C(=0), CH3CH2NHCH2C(=0), CH3CH2CH2CH2NHCH2C(=0) and CH3CH2NHCH2CH2C(=0).
  • The term “amide” means A-R′C═ONR″—B, wherein R′ and R″ indicates substituents and A and B indicate any group.
  • The term “thioamide” means A-R′C═SNR″—B, wherein R′ and R″ indicates substituents and A and B indicate any group.
  • The total number of carbon atoms in a substituent group is indicated by the “Ci-Cj” prefix where i and j are numbers from 1 to 21. For example, Ci-C alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2. In the above recitations, when a compound of Formula I is comprised of one or more heterocyclic rings, all substituents are attached to these rings through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
  • When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents. Further, when the subscript m in (R)m indicates an integer ranging from for example 0 to 4 then the number of substituents may be selected from the integers between 0 and 4 inclusive.
  • When a group contains a substituent which can be hydrogen, then, when this substituent is taken as hydrogen, it is recognized that said group is being un-substituted.
  • The embodiments herein and the various features and advantageous details thereof are explained with reference to the non-limiting embodiments in the description. Descriptions of well-known components and processing techniques are omitted so as to not unnecessarily obscure the embodiments herein. The examples used herein are intended merely to facilitate an understanding of ways in which the embodiments herein may be practiced and to further enable those of skilled in the art to practice the embodiments herein. Accordingly, the examples should not be construed as limiting the scope of the embodiments herein.
  • The description of the specific embodiments will so fully reveal the general nature of the embodiments herein that others can, by applying current knowledge, readily modify and/or adapt for various applications such specific embodiments without departing from the generic concept, and, therefore, such adaptations and modifications should and are intended to be comprehended within the meaning and range of equivalents of the disclosed embodiments. It is to be understood that the phraseology or terminology employed herein is for the purpose of description and not of limitation. Therefore, while the embodiments herein have been described in terms of preferred embodiments, those skilled in the art will recognize that the embodiments herein can be practiced with modification within the spirit and scope of the embodiments as described herein.
  • Any discussion of documents, acts, materials, devices, articles and the like that has been included in this specification is solely for the purpose of providing a context for the disclosure. It is not to be taken as an admission that any or all of these matters form a part of the prior art base or were common general knowledge in the field relevant to the disclosure as it existed anywhere before the priority date of this application.
  • The numerical values mentioned in the description and the description/claims though might form a critical part of the present invention of the present invention, any deviation from such numerical values shall still fall within the scope of the present invention if that deviation follows the same scientific principle as that of the present invention disclosed in the present invention. The inventive compounds of the present invention may, if appropriate, be present as mixtures of different possible isomeric forms, especially of stereoisomers, for example E and Z, threo and erythro, and also optical isomers, but if appropriate also of tautomers. Both the E and the Z isomers, and also the threo and erythro isomers, and the optical isomers, any desired mixtures of these isomers and the possible tautomeric forms are disclosed and claimed.
  • The term “pest” for the purpose of the present disclosure includes but is not limited to fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects and rodents.
  • The term “plant” is understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which are protectable and non-protectable by plant breeders' rights.
  • For the purpose of the present disclosure the term “plant” includes a living organism of the kind exemplified by trees, shrubs, herbs, grasses, ferns, and mosses, typically growing in a site, absorbing water and required substances through its roots, and synthesizing nutrients in its leaves by photosynthesis.
  • Examples of “plant” for the purpose of the present invention include but are not limited to agricultural crops such as wheat, rye, barley, triticale, oats or rice; beet, e.g. sugar beet or fodder beet; fruits and fruit trees, such as pomes, stone fruits or soft fruits, e.g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit and citrus trees, such as oranges, lemons, grapefruits or mandarins; any horticultural plants, vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; larvaceous plants, such as avocados, cinnamon or camphor; cucurbitaceae; oleaginous plants; energy and raw material plants, such as cereals, corn, soybean, other leguminous plants, rape, sugar cane or oil palm; tobacco; nuts; coffee; tea; cacao; bananas; peppers; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e.g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants.
  • Preferably, the plant for the purpose of the present invention include but is not limited to cereals, corn, rice, soybean and other leguminous plants, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbitaceae, oleaginous plants, tobacco, coffee, tea, cacao, sugar beet, sugar cane, cotton, potato, tomato, onions, peppers and vegetables, ornamentals, any floricultural plants and other plants for use of human and animals.
  • The term “plant parts” is understood to mean all parts and organs of plants above and below the ground. For the purpose of the present disclosure the term plant parts includes but is not limited to cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots including taproots, lateral roots, root hairs, root apex, root cap, rhizomes, slips, shoots, fruits, fruit bodies, bark, stem, buds, auxiliary buds, meristems, nodes and internodes.
  • The term “locus thereof” includes soil, surroundings of plant or plant parts and equipment or tools used before, during or after sowing/planting a plant or a plant part.
  • Application of the compounds of the present disclosure or the compound of the present disclosure in a composition optionally comprising other compatible compounds to a plant or a plant material or locus thereof include application by a technique known to a person skilled in the art which include but is not limited to spraying, coating, dipping, fumigating, impregnating, injecting and dusting.
  • The term “applied” means adhered to a plant or plant part either physically or chemically including impregnation.
  • Accordingly, novel oxadizole compounds of the present invention are represent by Formula I, N-oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof;
  • Figure US20220169621A1-20220602-C00003
  • wherein:
  • R1 is Ci-C2-haloalkyl;
  • L1 is a direct bond, —CR¾3—, —C(=0)-, —O—, —S(=0)O—, —NR4—, —CR2R3C(=0)-, —S(═O)0-2(—NR4)—, —SR5(=0)0-1(═N)—, —S(=0)0-1(═NR4)—, —SR5 (=0)0-1(═N)—CR2R3—, wherein, an expression “-” at the start and the end of the group indicates the point of attachment to either oxadiazole ring or A;
  • A is an aromatic or non-aromatic carbocyclic ring, wherein the ring members of the non-aromatic carbocyclic ring are selected from C, C(═0), C(═S), C(═CR2aR3a) and C═NR6; or
  • A is an aromatic or non-aromatic heterocyclic ring; wherein the heteroatom of the aromatic heterocyclic ring is selected from N, O and S; wherein heteroatom of the non-aromatic heterocyclic ring is selected from N, O, S(=0)0-2, and S(═O)0-1(═NR6) and one or more C atoms of the non-aromatic heterocyclic ring may be optionally replaced by C(=0), C(═S), C(═CR2aR3a) and C═NR6; and
  • wherein, A is unsubstituted or is substituted with one or more identical or different RA groups,
      • wherein, RA is selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, hydroxy, SF5, Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, C3-Cs-cycloalkyl, C3-C8-cycloalkylalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Cs-Cs-halocycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-Ce-haloalkoxycarbonyl, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-haloalkylsulfinyl, Ci-Ce-haloalkylsulfonyl, Ci-Ce-alkylvinyl, Ci-C6-alkylsulfonyl, Ci-C6-alkylamino, Ci-Ce-dialkylamino, C3-Cs-cycloalkylamino, Ci-Ce-alkyl-C3-(V-cycloalkylamino, Ci-Ce-alkylcarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylaminocarbonyl, Ci-C6-dialkylaminocarbonyl, Ci-C6-alkoxycarbonyloxy, Ci-C6-alkylaminocarbonyloxy, or Ci-C6-dialkylaminocarbonyloxy, 5- to 11-membered spirocyclic ring, and 3- to 6-membered carbocyclic or heterocyclic ring,
        • wherein, RA may be optionally substituted with one or more identical or different Ra selected from halogen, cyano, nitro, Ci-Ce-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C8-halocycloalkyl, Ci-C6-alkylamino, di-Ci-C6-alkylamino or C3-C8-cycloalkylamino;
        • wherein, 5- to 11-membered spirocyclic ring, 3- to 6-membered carbocyclic or heterocyclic ring may be optionally substituted with one or more identical or different substituents selected from halogen, cyano, nitro, hydroxy, Ci-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cyclo alkyl, C3-Cs-cycloalkylalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy alkyl, Ci-Ce-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C6-halocycloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-haloalkylsulfinyl, Ci-C6-haloalkylsulfonyl, Ci-C6-alkyl sulfinyl, Ci-C6-alkyl sulfonyl, Ci-C6-alkyl amino, di-Ci-C6-alkyl amino, C3-C6-cycloalkylamino, Ci-C6-alkyl-C3-C6-cycloalkylamino, Ci-Ce alkylcarbonyl, Ci-Ce-alkoxycarbonyl, Ci-C6-alkylaminocarbonyl, di-Ci-C6-alkyl aminocarbonyl, Ci-Ce-alkoxycarbonyloxy, Ci-C6-alkylaminocarbonyloxy, or di-Ci-C6-alkylaminocarbonyloxy, or
        • two RA together with the atoms to which they are attached may form a 3- to 10-membered aromatic or non-aromatic carbocyclic ring or ring system, or aromatic or non-aromatic heterocyclic ring or ring system which may be optionally substituted with one or more
          • identical or different Ra,
        • wherein, the C atom of the non-aromatic carbocyclic ring may be optionally replaced by C(=0), C(═S), C(═CR2bR3b) and C═NR6a or,
          • wherein, the heteroatom of the aromatic heterocyclic ring is selected from N, O and S; wherein heteroatom of the non-aromatic heterocyclic ring is selected from N, O, S(=0)0-2, and S(═O)o.i(═NR6a) and one or more C atoms of the non-aromatic heterocyclic ring may be optionally replaced by C(=0), C(═S), C(═CR2bR3b) and C═NR6a;
  • R4, R6, R6a, R6b, and R6c are independently selected from the group of hydrogen, cyano, hydroxy, NRbRc, (C=0)-Rd, S(O)0-2Re, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylamino, di-Ci-C6-alkylamino, tri-Ci-C6-alkylamino or C3-Cs-cycloalkyl;
      • Rb and Rc represent hydrogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C3-C8-cycloalkyl or C3-Cs-halocycloalkyl,
      • Rd represents hydrogen, hydroxy, halogen, NRbRc, Ci-Ce-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-Cs-cycloalkyl or C3-Cs-halocycloalkyl, and
      • Re represents hydrogen, halogen, cyano, Ci-Ce-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-Ce-haloalkoxy, C3-Cs-cycloalkyl or C3-Cs-halocycloalkyl,
  • L2 is a fragment selected from the group of
  • Figure US20220169621A1-20220602-C00004
  • wherein, k is an integer ranging from 0 to 4; an expression “#” on the left side indicates the point of attachment to A, and an expression “*” on the right side indicates the point of attachment to R10;
      • wherein, in Formula 1 when R1 is CF3, A is phenyl ring or C3-C7 carbocyclic ring or 5- to 6-membered heterocyclic ring; L2 is L2C and k=0 then R10 is not hydrogen, cyano, nitro, Ci-Csalkyl, C1-C3 haloalkyl;
      • wherein, in Formula I when R1 is CF3; A is phenyl ring or 5- to 6-membered heteroaromatic ring L2 is L2d and k=0 to 4 then R10 is not cyano, nitro, R11 and OR11;
        • wherein, R11 is hydrogen, Ci-C6-alkyl optionally substituted with a group selected from halogen, cyano, nitro, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-Ce-haloalkylthio, and phenyl ring optionally substituted with Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy,
  • R2, R3, R2a, R3a, R2b, R3b, R2c, R3c, R2d, R3d, R2e, R3e, R7 and R8 are independently selected from hydrogen, halogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-halo alkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkoxy or C1-C4-haloalkoxy, or
  • R2 and R3; R2a and R3s; R2b and R3b; R2e and R3e; R2d and R3d; R2e and R3e; and or R7 and R8 together with the atoms to which they are attached may form 3- to 5-membered non-aromatic carbocylic ring or heterocyclic ring which may be optionally substituted with halogen, Ci-C2-alkyl, Ci-C2-haloalkyl or Ci-C2-alkoxy;
  • R9 is independently selected from the group consisting of hydrogen; NRgRh, wherein, Rg and Rh independently represent hydrogen, hydroxyl, cyano, Ci-C4-alkyl, CiXX-haloalkyl, Ci-C4-alkoxy or C3-Cs-cycloalkyl; (C=0)-R′, wherein, R1 represents hydrogen, halogen, cyano, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4-haloalkynyl, C3-C6 cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy; Ci-s-alkyl-S(0)0-2R′, wherein R1 represents hydrogen, halogen, cyano, Ci-Ce-alkyl, CiXVhaloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, Cr-Cs-cycloalkyl; C1-C6-alkyl-(C=0)-Ri, CRi═NRg, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy, C3-Cs-cycloalkyl, C4-C8-cycloalkenyl, Cs-Cs-cycloalkynyl, C7-Ci9-aralkyl, bicyclic Cs-Cn-alkyl, C7-Ci2-alkenyl, fused or non-fused or bicyclic C3-Ci8-carbocyclic; wherein one or more carbon atoms in cyclic ring system may be replaced by N, O, S(═O)0-2, S(═O)0-1(═NR5c), C(═0), C(═S), C(═CR2eR3e) and C═NR6c,
      • wherein, R9 may optionally be substituted with one or more identical or different substituents selected from hydrogen, halogen, cyano, nitro, hydroxy, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-Cs-cycloalkyl, Cs-Cs-cycloalkylalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-Cs-halocycloalkyl, C1-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-haloalkoxycarbonyl, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-haloalkylsulfinyl, Ci-C6-haloalkylsulfonyl, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C1-C6-alkylamino, di-Ci-C6-alkylamino, C3-C8-cycloalkylamino, Ci-C6-alkyl-C3-C8-cycloalkylamino, Ci-C6-alkylcarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylaminocarbonyl, di-Ci-C6-alkylaminocarbonyl, Ci-C6-alkoxycarbonyloxy, Ci-C6-alkylaminocarbonyloxy, or di C1-C6-alkylaminocarbonyloxy, 5- to 11-membered spirocyclic ring, 3- to 6-membered carbocyclic or heterocyclic ring;
  • R10 is selected from the group of hydrogen, halogen, hydroxy, cyano, —OR12, —NR13R14, nitro, —SH, —SCN, —COR15, —C(═O)OR12, —C(═O)NR13R14, —NR13C(═O)R15, —O(C═O)R15, —O(C═O)NR13R14, —C(═NOR13)R15, —NR13SO2R16, —CSR16, —C(═S)OR12, —C(═S)NR13R14, —NR13C(═S)R15, —O(C═S)R15, —O(C═S)NR13R14, —O(C═S)SR16, —N═C(R15)2, —NHCN, —SO2NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO2NR12R13, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C1-C6-alkyl-C3-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C6-alkyl, Cs-Cs-cycloalkyl-Cb-(V cycloalkyl, C3-Cs-halocycloalkyl-Ci-C6-alkyl, Ci-C6-alkyl-Cs-Cs-cycloalkyl-Ci-C6-alkyl, Cs-Cs-cycloalkenyl, C3-Cs-halocycloalkenyl, Ci-C6-alkoxy-Ci-C6-alkyl, C3-C8-cycloalkoxy-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkyl-Ci-C6-thioalkyl, Ci-C6-alkylsulfinyl-Ci-C6-alkyl, C1-C6-alkylsulfonyl-Ci-C6-alkyl, Ci-C6-alkylamino, di-Ci-C6-alkylamino, Ci-C6-alkylamino-Ci-C6-alkyl, di-Ci-C6-alkylamino-Ci-C6-alkyl, Ci-C6-haloalkylamino-Ci-C6-alkyl, Cs-Cs-cycloalkylamino, C3-C8-cycloalkylamino-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkoxy-Ci-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, C3-C8-halocycloalkoxy, C3-C8-cycloalkyl-Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, Ci-C6-alkylcarbonylalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8-cycloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C3-Cs-cycloalkylsulfonyl, Cs-Cs-cycloalkylsulfinyl, tri-Ci-C6-alkylsilyl, Ci-C6-alkylsulfonylamino, Ci-C6-haloalkylsulfonylamino, Ci-C6-alkylcarbonylthio, C1-C6-alkylsulfonyloxy, Ci-C6-alkylsulfinyloxy, C6-C10-arylsulfonyloxy, C6-C10-arylsulfinyloxy, Ce-Cio-arylsulfonyl, C6-C10-arylsulfinyl, C6-C10-arylthio, C1-C6-cyanoalkyl, C2-C6-alkenylcarbonyloxy, C1-C6-alkoxy-Ci-C6-alkylthio, Ci-C6-alkylthio-Ci-C6-alkoxy, C2-C6-haloalkenylcarbonyloxy, Ci-C6-alkoxycarbonyl-Ci-C6alkyl, C1-C6-alkoxy-C2-C6-alkynyl, C2-C6-alkynylthio, C3-C-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C5-cycloalkyl-Ci-C6-alkylamino, Ci-C6-alkoxyamino, Ci-C G-haloalkoxyamino, Ci-C6-alkoxycarbonylamino, C i-C6-alkylcarbonyl-Ci-C6-alkylamino, Ci-C6-haloalkylcarbonyl-Ci-C6-alkylamino, Ci-C6-alkoxycarbonyl-Ci-C6-alkylamino, C2-C6-alkenylthio, Ci-C6-alkoxy-Ci-C6-alkylcarbonyl, Ci-C6-haloalkoxycarbonylamino, di(Ci-C6-haloalkyl)amino-Ci-C6-alkyl, C3-C5-halocycloalkenyloxy-Ci-C6-alkyl, Ci-C6-alkoxy(Ci-C6-alkyl)aminocarbonyl, Ci-C6-haloalkylsulfonylaminocarbonyl, Ci-C6-alkylsulfonylaminocarbonyl, Ci-C6-alkoxycarbonylalkoxy, Ci-C6-alkylaminothiocarbonylamino, C3-C8-cycloalkyl-Ci-C6-alkylamino-Ci-C6-alkyl, Ci-C6-alkylthiocarbonyl, C3-C5-cycloalkenyloxy-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkoxycarbonyl, di-C1-C6-alkylaminothiocarbonylamino, Ci-C6-haloalkoxy-Ci-C6-haloalkoxy, Ci-C6-alkoxy-Ci-C6-haloalkoxy, C3-C8-halocycloalkoxy-Ci-C6-alkyl, di-Ci-C6-alkylaminocarbonylamino, Ci-C6-alkoxy-C2-C6-alkenyl, Ci-C6-alkylthiocarbonyloxy, Ci-C6-haloalkoxy-Ci-C6-alkoxy, Ci-C6-haloalkylsulfonyloxy, Ci-C6-alkoxy-Ci-C6-haloalkyl, di(Ci-C6-haloalkyl)amino, di-Ci-C6-alkoxy-Ci-Ce-alkyl, C1-C6-alkylaminocarbonylamino, Ci-C6-haloalkoxy-Ci-C6-haloalkyl, Ci-Ce-alkylaminocarbonyl-Ci-C6-alkylamino, tri-Ci-C6-alkylsilyl-C2-C6-alkynyloxy, tri-Ci-Ce-alkylsilyloxy, tri-Ci-C6-alkylsilyl-C2-C6-alkynyl, cyano(Ci-C6-alkoxy)-Ci-C6-alkyl, di-Ci-Ce-alkylthio-Ci-C6-alkyl, C1-C6-alkoxysulfonyl, C3-Cs-halocycloalkoxycarbonyl, Ci-C6-alkyl-C3-C5-cycloalkylcarbonyl, C3-Cs-halocycloalkylcarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6 alkynyloxycarbonyl, C1-C6-cyanoalkoxycarbonyl, Ci-C6-alkylthio-Ci-C6-alkoxycarbonyl, C2-C6 alkynylcarbonyloxy, C2-C6-haloalkynylcarbonyloxy, cyanocarbonyloxy, Ci-Ce-cyanoalkylcarbonyloxy, C3-C5-cycloalkylsulphonyloxy, C3-C5-cycloalkyl-Ci -C6-alkylsulphonyloxy, Cs-Cs-halocycloalkylsulphonyloxy, C2-C6-alkenylsulphonyloxy, C2-C6-alkynylsulphonyloxy, Ci-Ce-cyanoalkylsulphonyloxy, C2-C6-haloalkenylsulphonyloxy, C2-C6-haloalkynylsulphonyloxy, C2-C6-alkynylcycloalkyloxy, C2-C6-cyanoalkenyloxy, C2-C6-cyanoalkynyloxy, Ci-C6-alkoxycarbonyloxy, C2-C6-alkenyloxycarbonyloxy, C2-C6-alkynyloxycarbonyloxy, Ci-C6-alkoxy-Ci-C6-alkylcarbonyloxy, sulfilimines, sulfoximines, SF5 or Z1Q1;
      • Z1 and Z2 are independently a direct bond, CR2dR3d, N, O, C(O), C(S), C(═CR2dR3d) or S(0)O2;
      • Q1 and Q2 are independently selected from phenyl, benzyl, naphthalenyl, a 5- or 6-membered aromatic ring, an 8- to 11-membered aromatic multi-cyclic ring system, an 8- to 11-membered aromatic fused ring system, a 5- or 6-membered heteroaromatic ring, an 8- to 11-membered heteroaromatic multi-cyclic ring system or an 8- to 11-membered heteroaromatic fused ring system; wherein the heteroatom of the heteroaromatic rings is selected from N, O or S, and each ring or ring system may be optionally substituted with one or more substituents independently selected from R7; or
      • Q1 and Q2 are independently selected from a 3- to 7-membered non-aromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered non-aromatic heterocyclic ring, an 8- to 15-membered non-aromatic multi-cyclic ring system, an 5- to 15 membered spirocyclic ring system, or an 8- to 15-membered non-aromatic fused ring system, wherein, the heteroatom of the non-aromatic rings is selected from N, O or S(O)0-2, and C ring member of the non-aromatic carbocylic or non-aromatic heterocyclic rings or ring systems may be replaced with C(O), C(S), C(═CR2cR3c) or C(═NR6b), and each ring or ring system may be optionally substituted with one or more substituents independently selected from R17;
      • wherein, R17 is selected from hydrogen, halogen, hydroxy, cyano, —OR12, —NR13R14, nitro, —SH, —SCN, —COR15, —C(═O)OR12, —C(═O)NR13R14, —NR13C(═O)R15, —O(C═O)R15, —O(C═O)NR13R14, —C(═NOR13)R15, —NR13SO2R16, —CSR16, —C(═S)OR12, —C(═S)NR13R14, —NR13C(═S)R15, —O(C═S)R15, —O(C═S)NR13R14, —O(C═S)SR16, —N═C(R15)2, —NHCN, —SO2NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO2NR12R13, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-Cs-cycloalkyl, C3-Cs-halocycloalkyl, Ci-Ce-alkyl-Cs-Cx-cycloalkyl, C3-Cs-cycloalkyl-Ci-C6-alkyl, Cs-CVcycloalkyl-Cs-Cx-cycloalkyl, C3-Cs-halocycloalkyl-Ci-Ce-alkyl, Ci-Ce-alkyl-Cs-Cs-cycloalkyl-Ci-Ce-alkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, Ci-C6-alkoxy-Ci-C6-alkyl, C3-Cs-cycloalkoxy-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkoxy-Ci-C6-alkyl, Ci-Ce-alkyl-Ci-Ce-thioalkyl, Ci-G,-alkylsulfinyl-Ci-Ce-alkyl, Ci-Ce-alkylsulfonyl-Ci-C6-alkyl, Ci-C6-alkylamino, di-Ci-C6-alkylamino, Ci-C6-alkylamino-Ci-C6-alkyl, di-Ci-C6-alkylamino-Ci-C6-alkyl, Ci-C6-haloalkylamino-Ci-C6-alkyl, Cr(V cycloalkylamino, C3-C8-cycloalkylamino-Ci-C6-alkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkoxy-Ci-C6-alkyl, Ci-Ce-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, Cs-Cs-halocycloalkoxy, C3-C8-cycloalkyl-Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, Ci-C6-alkylcarbonylalkoxy, Ci-C6-alkylthio, Ci-Ce-haloalkylthio, C3-C8-cycloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C3-Cs-cycloalkylsulfonyl, Cs-Cs-cycloalkylsulfinyl, tri-Ci-C6-alkylsilyl, Ci-C6-alkylsulfonylamino, Ci-C6-haloalkylsulfonylamino, Ci-C6-alkylcarbonylthio, Ci-Ce-alkylsulfonyloxy, Ci-C6-alkylsulfinyloxy, C6-Cio-arylsulfonyloxy, C6-Cio-arylsulfinyloxy, Ce-Cio-arylsulfonyl, C6-Cio-arylsulfinyl, C6-Cio-arylthio, Ci-C6-cyanoalkyl, C2-C6-alkenylcarbonyloxy, Ci-C6-alkoxy-Ci-C6-alkylthio, Ci-C6-alkylthio-C1-C6-alkoxy, C2-C6-haloalkenylcarbonyloxy, Ci-Ce-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-alkoxy-C2-C6-alkynyl, C2-C6-alkynylthio, C3-C8-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, Ci-C6-haloalkylamino, C3-C8-cycloalkyl-Ci-C6-alkylamino, Ci-C6-alkoxyamino, Ci-C6-haloalkoxyamino, Ci-Ce-alkoxycarbonylamino, Ci-C6-alkylcarbonyl-C1-C6-alkylamino, Ci-C6-haloalkylcarbonyl-C1-Ce-alkylamino, Ci-C6-alkoxycarbonyl-Ci-C6-alkylamino, C2-C6-alkenylthio, Ci-C6-alkoxy-Ci-C6-alkylcarbonyl, Ci-C6-haloalkoxycarbonylamino, di(Ci-C6-haloalkyl)amino-Ci-C6-alkyl, C3-C8-halocycloalkenyloxy-Ci-C6-alkyl, Ci-C6-alkoxy(Ci-C6-alkyl)aminocarbonyl, Ci-Ce-haloalkylsulfonylaminocarbonyl, Ci-C6-alkylsulfonylaminocarbonyl, Ci-C6-alkoxycarbonylalkoxy, Ci-C6-alkylaminothiocarbonylamino, C3-Cs-cycloalkyl-Ci-C6-alkylamino-Ci-C6-alkyl, Ci-Ce-alkylthiocarbonyl, C3-Cs-cycloalkenyloxy-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkoxycarbonyl, di-Ci-C6-alkylaminothiocarbonylamino, Ci-C6-haloalkoxy-Ci-C6-haloalkoxy, Ci-C6-alkoxy-Ci-C6-haloalkoxy, C3-Cs-halocycloalkoxy-Ci-C6-alkyl, di-Ci-C6-alkylaminocarbonylamino, Ci-C6-alkoxy-C2-C6-alkenyl, Ci-C6-alkylthiocarbonyloxy, Ci-C6-haloalkoxy-Ci-C6-alkoxy, Ci-Ce-haloalkylsulfonyloxy, Ci-C6-alkoxy-Ci-C6-haloalkyl, di(Ci-C6-haloalkyl)amino, di-Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylaminocarbonylamino, Ci-C6-haloalkoxy-Ci-C6-haloalkyl, Ci-Ce-alkylaminocarbonyl-Ci-C6-alkylamino, tri-Ci-C6-alkylsilyl-C2-C6-alkynyloxy, tri-Ci-Ce-alkylsilyloxy, tri-Ci-C6-alkylsilyl-C2-C6-alkynyl, cyano(Ci-C6-alkoxy)-Ci-C6-alkyl, di-Ci-Ce-alkylthio-Ci-C6-alkyl, Ci-C6-alkoxysulfonyl, Cs-Cs-halocycloalkoxycarbonyl, Ci-C6-alkyl-C3-C8-cycloalkylcarbonyl, Cs-Cs-halocycloalkylcarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6-alkynyloxycarbonyl, Ci-C6-cyanoalkoxycarbonyl, Ci-C6-alkylthio-Ci-C6-alkoxycarbonyl, C2-C6-alkynylcarbonyloxy, C2-C6-haloalkynylcarbonyloxy, cyanocarbonyloxy, Ci-Ce-cyanoalkylcarbonyloxy, Cs-Cs-cycloalkylsulphonyloxy, C3-Cs-cycloalkyl-Ci-C6-alkylsulphonyloxy, Cs-Cs-halocycloalkylsulphonyloxy, C2-C6-alkenylsulphonyloxy, C2-C6-alkynylsulphonyloxy, Ci-Ce-cyanoalkylsulphonyloxy, C2-C6-haloalkenylsulphonyloxy, C2-C6-haloalkynylsulphonyloxy, C2-C6-alkynylcycloalkyloxy, C2-C6-cyanoalkenyloxy, C2-C6-cyanoalkynyloxy, Ci-C6-alkoxycarbonyloxy, C2-C6-alkenyloxycarbonyloxy, C2-C6-alkynyloxycarbonyloxy, Ci-C6-alkoxy-Ci-C6-alkylcarbonyloxy, sulfilimines, sulfoximines, SF5 or Z2Q2;
      • R9 and R10; and or R9 and RA together with the atoms to which they are attached may form a 3- to 10-membered carbocyclic ring or ring system, or heterocyclic ring or ring system which may be optionally substituted with R17;
        • wherein,
          • R12 represents Ci-Ce-alkyl, Ci-C6-haloalkyl, CvCs-cycloalkyl, C3-C8-halocycloalkyl,
      • R13 and R14 independently represent hydrogen, hydroxyl, cyano, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-C6-alkoxy, CvCs-cycloalkyl, C3-C8-halocycloalkyl,
      • R15 represents hydrogen, hydroxy, halogen, NRbRc, Ci-Ce-alkyl, Ci-C6-haloalkyl, C1-C6-alkoxy, Ci-C6-haloalkoxy, CvCs-cycloalkyl, CvCs-cycloalkyl, and
      • R16 represents hydrogen, halogen, cyano, CiXValkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-Ce-haloalkoxy, C3-Cs-cycloalkyl, or C3-Cs-cycloalkyl.
  • Particularly, a carbon atom of R1 from the oxadiazole ring bears at least two fluorine atoms; and the 9 carbon atom of R1 from the oxadiazole ring in case of C2-haloalkyl bears at least one fluorine atom.
  • Particularly, the present invention relates a compound of Formula I, wherein:
  • R1 is trifluoroalkyl;
  • L1 is a direct bond;
  • A is a phenyl ring or pyridyl ring; wherein phenyl or pyridyl ring is unsubstituted or substituted with one or more identical or different RA groups,
      • wherein, RA is halogen, cyano, Ci-C6-alkyl and Ci-C6-alkoxy,
        • wherein RA may be optionally substituted with one or more identical or different Ra selected from halogen, cyano, and amino;
  • L2 is a fragment selected from the group of
  • Figure US20220169621A1-20220602-C00005
  • wherein, k is an integer ranging from 0 to 1; an expression “#” on the left side indicates the point of attachment to A, and an expression “*” on the right side indicates the point of attachment to R10;
  • R7 and R8 are hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, or C1-C4-alkoxy;
  • R9 is selected from the group consisting of Ci-Ce-alkyl, C2-C6-alkenyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, and C3-Cs-cycloalkyl;
  • R10 is selected from the group of Ci-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-Cs-cycloalkyl, C3-Cs-halocycloalkyl, Ci-C6-alkyl-C3-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C6-alkyl, C3-C8-cycloalkyl-Ci-CVcycloalkyl, C3-Cs-halocycloalkyl-Ci-Ce-alkyl, Ci-Ce-alkyl-Cs-Cs-cycloalkyl-Ci-Ce-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, C3-C8-cycloalkoxy-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-haloalkoxy-Ci-C6-alkyl, Ci-C6-hydroxyalkyl, C3-Cs-halocycloalkoxy, Cb-C8-cycloalkyl-Ci-Ce-alkoxy, Ci-Ce-alkoxy-Ci-Ce-alkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkylthio, Ci-C6-alkylsulfinyl, Ci-Ce-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, Cs-Cs-cycloalkylsulfonyl, C3-C8-cycloalkylsulfinyl or Z3Q3;
      • Z1 and Z2 are independently a direct bond, CR2dR3d, and O;
      • Q1 and Q2 are phenyl, benzyl, 5- or 6-membered aromatic ring, a 5- or 6-membered heteroaromatic ring; wherein the heteroatom of the heteroaromatic ring is selected from N, O and S; and each ring may be optionally substituted with one or more substituents independently selected from R17; or
      • wherein, R17 is selected from halogen, cyano, —OR12; wherein R12 represents CiXValkyl, C1-C6-haloalkyl, Cs-CVcycloalkyl and C3-C<<halocycloalkyl; Ci-Ce-alkyl, Cz-Ce-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-Cs-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkyl-C3-Cs-cycloalkyl, Ci-Ce-alkylthio, Ci-Ce-haloalkylthio, C3-C8-cycloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-Ce-haloalkylsulfonyl, Cs-Cs-cycloalkylsulfonyl, C3-(V cycloalkylsulinyl and Z2Q2;
  • R9 and R10 together with the atoms to which they are attached may form a 3- to 10-membered heterocyclic ring or ring system which may be optionally substituted with R17; wherein the heteroatom of the heterocyclic ring or ring system is selected from N, O and S(O)0-2.
  • More particularly, the compound of Formula I is selected from the group consisting of:
  • N-(methyl(oxo)(p-tolyl)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-cyanobenzyl)(methyl)(oxo)-′/.6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,6-difluorobenzyl)(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,3-difluorobenzyl)(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-methoxybenzyl)(methyl)(oxo)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-bromobenzyl)(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,6-difluorophenyl)(methyl)(oxo)-X6-sulfanylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,4-difluorobenzyl)(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorobenzyl)(methyl)(oxo)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((3-fluorobenzyl)(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(2-methyl benzyl)(oxo)-′/.6-sulfanylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((3,5-dimethylphenyl)(methyl)(oxo)-′/.6-sulfanylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-cyanophenyl)(methyl)(oxo)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(1-oxidotetrahydro-2H-1λ6-thiopyran-1-ylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(m-tolyl)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(3-methylbenzyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((3-methoxyphenyl)(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,4-difluorophenyl)(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(thiazol-2-yl)-X6-sulfanylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-fluorobenzyl)(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl((oxo)(4-(trifluoromethyl)benzyl)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,6-dichlorobenzyl)(methyl)(oxo)-/.6-sulfanylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(pyridin-2-yl)methyl)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(4-methylthiazol-2-yl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(5-methyl-1,3,4-thiadiazol-2-yl)(oxo)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,5-dichlorophenyl)(methyl)(oxo)-′/.6-sulfanylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,4-dimethoxyphenyl)(methyl)(oxo)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((3,4-difluorophenyl)(methyl)(oxo)-λ6-sulfanylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(4-oxido-1,4′/.6-oxathian-4-ylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorophenyl)(methyl)(oxo)-λ6-sulfanylidene)-4-(3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)benzamide; N-(methyl(oxo)(pyridin-4-ylmethyl)-′/.6-sulfancylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorobenzyl)(methyl)(oxo)-′/.6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chloro-3-fluorobenzyl)(methyl)(oxo)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,5-difluorobenzyl)(methyl)(oxo)-′/.6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorophenyl)(methyl)(oxo)-λ6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(4-(trifluoromethyl)phenyl)-′/.6-sulfancylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-fluorophenyl)(methyl)(oxo)-′/.6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(pyridin-2-yl)-6-sulfanylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(phenyl)-λ6-sulfancylidone)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,6-difluorobenzyl)(methyl)(oxo)-′/.6-sulfancylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,4-difluorobenzyl)(methyl)(oxo)-λ6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-methoxybenzyl)(methyl)(oxo)-/.6-sulfancylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-methoxyphenyl)(methyl)(oxo)-′/.6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,6-difluorophenyl)(methyl)(oxo)-′/.6-sulfaneylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(thiazol-2-yl)-′/.6-sulfancylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(1-oxidotetrahydro-2H-′/.-thiopyran-1-ylidene)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-cyanobenzyl)(methyl)(oxo)-′/.6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-fluorophenyl)(isopropyl)(oxo)-′/.6-sulfancylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isopropyl(4-methoxyphenyl)(oxo)-′/.6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorophenyl)(isopropyl)(oxo)-′/.6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isopropyl(oxo)(pyridin-2-yl)-6-sulfancylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isopropyl(oxo)(phenyl)-′/.6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-fluoro-N-((4-methoxyphenyl)(methyl)(oxo)-′/.6-sulfancylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((3-bromophenyl)(ethyl)(oxo)-′/.6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(2-phenoxyethyl)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; (2,6-difluorophenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-X6-sulfanone; (2,6-difluorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-X6-sulfanone; (2,4-difluorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanone; (2,3-difluorobenzyl)(meth yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-X6-sulfanone; methyl(2-methyl benzyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanone; (4-fluorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-′/.6-sulfanone; methyl((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(4-(trifluoromethyl)benzyl)-//′-sulfanone; (2,6-dichlorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanone; (4-bromobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanone; methyl(pyridin-2-ylmethyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanone; (2-fluorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanone; (3-fluorobenzyl)(meth yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanone; (2,4-dimethoxyphenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanone; (3,4-difluorophenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-′/.6-sulfanone; (4-chlorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-′/.6-sulfanone; (4-chloro-3-fluorobenzyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-λ6-sulfanone; (4-methoxyphenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-X6-sulfanone; (3-methoxyphenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-X6-sulfanone; 1-((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)hexahydro-‘//’-thiopyran 1-oxide; (2,4-dimethoxyphenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-)λ6-sulfanone; (4-fluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-λ6-sulfanone; (2-fluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-λ6-sulfanone; (3-methoxyphenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-λ6-sulfanone; (2,5-dichlorophenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-λ6-sulfanone; (4-methoxyphenyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-λ6-sulfanone; methyl(phenyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-λ6-sulfanone; methyl(pyridin-2-yl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-ylimino)-λ6-sulfanone; (2,6-difluorobenzyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-λ6-sulfanone; (4-chlorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-λ6-sulfanone; methyl(pyridin-2-yl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-λ6-sulfanone; methyl(m-tolyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-λ6-sulfanone; methyl(thiazol-2-yl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-λ6-sulfanone; methyl((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(4-(trifluoromethyl)pyridin-2-yl)-λ6-sulfanone; methyl(4-methylthiazol-2-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-λ6-sulfanone; methyl(thiazol-2-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-λ6-sulfanone; (4-chlorophenyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-λ6-sulfanone; (2,6-difluorophenyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-λ6-sulfanone; (3,4-difluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-λ6-sulfanone; methyl(phenyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-λ6-sulfanone; (4-fluorophenyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-λ6-sulfanone; methyl((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)(4-(trifluoromethyl)phenyl)-‘//’-sulfanone; (2-fluorophenyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-‘//’-sulfanone; (4-fluorobenzyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-λ6-sulfanone; (3-methoxyphenyl)(methyl)((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-X6-sulfanone; 1-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyri din-3-yl)imino)hexahydro-‘//’-thiopyran 1-oxide; 4-((6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-3-yl)imino)-1,4X6-oxathiane 4-oxide; methyl(p-tolyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanoic; (2,4-difluorophenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanone; methyl((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(5-(trifluoromethyl)pyridin-2-yl)-‘//’-sulfanoric; 4-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-1,4‘//’-oxathiane 4-oxide; 1-((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)hexahydro-‘//’-thiopyran 1-oxide; methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-′/.6-sulfanoric; methyl(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanoric; methyl(p-tolyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzylimino)-‘//’-sulfanoric; methyl(phenyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-‘//’-sulfanoric; (4-methoxyphenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzylimino)-‘//’-sulfanoric; (2,4-dimethoxyphenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/.6-sulfanoric; (3,4-difluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/.6-sulfanoric; methyl((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)(4-((4-(trifluoromethyl)pyridin-2-yl)oxyphenyl)-′/.6-sulfanoric; (4-chlorophenyl)(methyl) (3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/.6-sulfanoric; methyl(thiazol-2-yl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/.6-sulfanoric; (4-fluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/.6-sulfanoric; (2-bromo-5-fluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-X6-sulfanone; 4-fluoro-N-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)benzenesulfonamide; (4-bromo-2-fluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/.6-sulfanone; (2-fluorophenyl)(methyl)((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl((benzyl)imino)-′/.6-sulfanone; 4-((3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-1,4-′/.6-oxathiane 4-oxide; isopropyl(4-methoxyphenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-λ6-sulfanone; isopropyl(phenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-X6-sulfanone; (4-chlorophenyl)(isopropyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-//′-sulfanone; N-tosyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((5-chloro-2-methoxyphenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,4-dichlorophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-methoxyphenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((3-methoxyphenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-N-((4-(trifluoromethyl)phenyl)sulfonyl)benzamide; N-(pyridin-3-ylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,5-difluorophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-bromophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,6-dichlorophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((3-fluorophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; ((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(2-fluorophenyl)(methyl)-′/.6-sulfanone; ((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)(phenyl)-‘//’-sulfanoric; (4-chlorophenyl)((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)-λ6-sulfanone; ((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)(pyridin-2-yl)-‘//’-sulfanoric; ((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(3-fluorophenyl)(methyl)-‘//’-sulfanoric; ((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(4-fluorophenyl)(methyl)-‘//’-sulfanoric; ((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(4-methoxyphenyl)(methyl)-‘//’-sulfanoric; 2-fluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfaneylidene)benzamide; 3-methoxy-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfaneylidene)benzamide; 3-fluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfaneylidene)benzamide; 4-chloro-2-fluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfaneylidene)benzamide; 2-chloro-6-fluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfancylidene)benzamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfaneylidene)benzamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfaneylidene)-2-phenylacetamide; 4-chloro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfaneylidene)benzamide;N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfaneylidene)pivalamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfaneylidene)cyclopropanecarboxamide; ((3-chlorobenzyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.6-sulfanoic; ((4-fluorobenzyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfanone; ((2,4-difluorobenzyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfanone; ((3-fluorobenzyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.6-sulfanoric; N-((4-fluorophenyl)(methyl)(oxo)-/.6-sulfaneylidene)-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide; ((2,4-difluorophenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.6-sulfanoric; ((2-fluoro-4-methoxyphenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.6-sulfanoric; ((2-fluorophenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.6-sulfanoric; ((2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(4-methoxyphenyl)(methyl)-X6-sulfanone; ((2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)(phenyl)-′/.6-sulfanoric; ((2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)(pyridin-2-yl)-′/.6-sulfanoric; ((2-methoxyphenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-‘//’-sulfanone; ((3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(2-fluorobenzyl)(trifluoromethyl)-′/.6-sulfanoric; ((3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(2-fluorophenyl)(trifluoromethyl)-X6-sulfanone; ((3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(4-methoxyphenyl)(trifluoromethyl)-′/.6-sulfanone; ((3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(phenyl)(trifluoromethyl)-X6-sulfanone; ((3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(pyridin-2-yl)(trifluoromethyl)-λ6-sulfanone; ((3-fluorophenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.6-sulfanone; ((4-fluorophenyl)imino(methyl)(4-(5-(trifluromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.6-sulfanone; ((4-methoxyphenyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.6-sulfanone; ((5-methoxypyridin-2-yl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.6-sulfanone; (2-(dimethylamino)ethyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′/.6-sulfanone; (2-(dimethylamino)ethyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/.6-sulfanone; (2,4-difluorophenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′/.6-sulfanone; (2-fluoro-4-methoxyphenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-λ6-sulfanone; (2-fluoro-4-methoxyphenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/.6-sulfanone; (2-fluorobenzyl)((2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)-′/.6-sulfanone; (2-fluorobenzyl)((3-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)-′/.6-sulfanone; (2-fluorobenzyl)(isopropyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-′/.6-sulfanone; (2-fluorobenzyl)(methyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)imino)-′/.6-sulfanone; (2-fluorobenzyl)(methyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidin-2-yl)imino)-i6-sulfanone; (2-fluorobenzyl)(trifluoromethyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-′/.6-sulfanone; (2-fluorophenyl)((2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(methyl)-‘//’-sulfanoic; (2-fluorophenyl)(isopropyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanoic; (2-fluorophenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-‘//’-sulfanoric; (2-fluorophenyl)(methyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)imino)-′/.6-sulfanoric; (2-fluorophenyl)(methyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidin-2-yl)imino)-X6-sulfanone; (2-fluorophenyl)(trifluoromethyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanone; (2-methoxyethyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-‘//’-sulfanoric; (2-methoxyethyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-X6-sulfanone; (2-methoxyphenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-‘//’-sulfanone; (3-fluorophenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-‘//’-sulfanoric; (3-fluoropyridin-4-yl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-‘//’-sulfanone; (3-methoxyphenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′//-sulfanone; (3-methoxypyridin-4-yl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-‘//’-sulfanone; (3-methoxypyridin-4-yl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/.6-sulfanone; (4-(difluoromethyl)phenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-′/.6-sulfanone; (4-fluoro-2-methoxyphenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-λ6-sulfanone; (4-fluoro-2-methoxyphenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/.6-sulfanone; (4-fluorophenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′/.6-sulfanone; (4-methoxyphenyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′/.6-sulfanone; (4-methoxyphenyl)(methyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)imino)-′/.6-sulfanone; (4-methoxyphenyl)(methyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidin-2-yl)imino)-X6-sulfanone; (4-methoxyphenyl)(trifluoromethyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-′/.6-sulfanone; (cyclobutyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.6-sulfanone; (cyclobutylmethyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′/.6-sulfanone; (cyclobutylmethyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′/.6-sulfanone; (cyclohexyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.6-sulfanone; (cyclopentyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.6-sulfanone; (cyclopentyl)methyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′/.6-sulfanone; (cyclopentylmethyl)(methyl)((4-(5-(trifluoromethyl 1,2,4-oxadiazol-3-yl)benzyl)imino)-′/.6-sulfanone; (cyclopropylimino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′/.6-sulfanone; (cyclopropylmethyl)(2-fluorobenzyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-′/.6-sulfanone; (cyclopropylmethyl)(2-(trifluorophenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-′/.6-sulfanone; (cyclopropylmethyl)(4-methoxyphenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanone; (cyclopropylmethyl)(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-‘//’-sulfanone; (cyclopropylmethyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-‘//’-sulfanone; (cyclopropylmethyl)(phenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanone; (cyclopropylmethyl)(pyridin-2-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-‘//’-sulfanone; (furan-3-ylimino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-‘//’-sulfanone; 1-methyl-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-‘//’-sulfancylidene)-1H-imidazole-4-carboxamide; 1-meth yl-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfancylidene)-1H-imidazole-5-carboxamide; 2,4-difluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-‘//’-sulfancylidene)benzamide; 2-fluoro-4-methoxy-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-‘//’-sulfancylidene)benzamide; 2-fluoro-N-((2-fluorobenzyl)(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-fluoro-N-((2-fluorophenyl)(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-fluoro-N-((4-methoxyphenyl)(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-fluoro-N-(4-oxido-1,4X6-oxathian-4-ylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-fluoro-N-(methyl(oxo)(pyridin-2-yl)-λ6. sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-fluoro-N-(methyl(oxo)(pyridin-4-yl)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-methoxy-N-((4-methoxyphenyl)(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-methoxy-N-(4-oxido-1,4X6-oxathian-4-ylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-methoxy-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfaneylidene)benzamide; 2-methoxy-N-(methyl(oxo)(pyridin-2-yl)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 2-methoxy-N-(methyl(oxo)(pyridin-4-yl)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-fluoro-N-((2-fluorobenzyl)(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-fluoro-N-((2-fluorophenyl)(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-fluoro-N-(4-oxido-1,4X6-oxathian-4-ylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-fluoro-N-(methyl)(oxo)(pyridin-2-yl)-′./6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-fluoro-N-(methyl(oxo)(pyridin-4-yl)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-methoxy-N-((4-methoxyphenyl)(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-methoxy-N-(4-oxido-1,4X6-oxathian-4-ylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-methoxy-N-(methyl(oxo)(pyridin-2-yl)-i6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 3-methoxy-N-(methyl(oxo)(pyridin-4-yl)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; 4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-N-((trifluoromethyl)sulfonyl)benzamide; 4-fluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfaneylidene)benzamide; 4-methoxy-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfaneylidene)benzamide; 5-methoxy-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-λ6-sulfaneylidene)picolinamide; allyl(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′./6-sulfanoric; allyl(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-i6-sulfanoric; allyl(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-i6-sulfanoric; cyclopentyl(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-i6-sulfanoric; cyclopropyl(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-i6-sulfanoric; cyclopropyl(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′./6-sulfanoric; cyclopropyl(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-′./6-sulfanoric; isobutyl(methyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-i6-sulfanoric; isobutyl(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′./6-sulfanoric; isobutyl(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-i6-sulfanoric; isopropyl(4-methoxyphenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-i6-sulfanoric; isopropyl(phenyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-i6-sulfanoric; isopropyl(pyridin-2-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-i6-sulfanoric; methyl((1-methyl-1H-imidazol-4-yl)imino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-i6-sulfanoric; methyl((1-methyl-1H-imidazol-5-yl)imino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′./6-sulfanoric; methyl(oxazol-4-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′./6-sulfanoric; methyl(oxazol-4-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-X6-sulfanone; methyl(oxazol-5-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-7i6-sulfanoric; methyl(oxazol-5-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-X6-sulfanone; methyl(oxazol-5-ylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfanone; methyl(perfluoroethyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-X6-sulfanone; methyl(perfluoroethyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-X6-sulfanone; methyl(phenyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-X6-sulfanone; methyl(phenyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)imino)-X6-sulfanone; methyl(phenyl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidin-2-yl)imino)-X6-sulfanone; methyl(phenylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfanone; methyl(prop-2-yn-1-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-X6-sulfanone; methyl(prop-2-yn-1-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-X6-sulfanone; methyl(prop-2-yn-1-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-X6-sulfanone; methyl(pyridin-2-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-X6-sulfanone; methyl(pyridin-2-yl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)imino)-X6-sulfanone; methyl(pyridin-2-yl)((5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidin-2-yl)imino)-X6-sulfanone; methyl(pyridin-2-ylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfanone; methyl(pyridin-3-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-X6-sulfanone; methyl(pyridin-4-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-X6-sulfanone; methyl(pyrimidin-2-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-λ6-sulfanone; methyl(pyrimidin-2-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-X6-sulfanone; methyl(pyrimidin-2-ylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfanone; methyl(pyrimidin-4-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′./6-sulfanone; methyl(pyrimidin-4-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′./6-sulfanoic; methyl(pyrimidin-4-ylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′./6-sulfanone; methyl(thiazol-4-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′./6-sulfanoric; methyl(thiazol-4-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′./6-sulfanoric; methyl(thiazol-5-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′./6-sulfanoric; methyl(thiazol-5-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′./6-sulfanoric; methyl(thiazol-5-ylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-λ6-sulfanone; methyl(thiophen-2-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′./6-sulfanone; methyl(thiophen-2-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′./6-sulfanone; methyl(thiophen-2-ylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-λ6-sulfanone; methyl(thiophen-3-yl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′./6-sulfanone; methyl(thiophen-3-yl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′./6-sulfanone; methyl(thiophen-3-ylimino)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′./6-sulfanone; methyl(trifluoromethyl)((4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)phenyl)imino)-′./6-sulfanone; methyl(trifluoromethyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-′./6-sulfanone; N-(((1-methylazetidin-3-yl)methyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-(dimethylamino)ethyl)(methyl)(oxo)-λ6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((2-(dimethylamino)ethyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-(dimethylamino)ethyl)sulfonyl)-N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2,4-di fluorophenyl)(methyl)(oxo)-λ6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((2-fluoro-4-methoxyphenyl)(methyl)(oxo)-X6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((2-(fluorobenzyl)(methyl)(oxo)-λ6-sulfaneylidene)-2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorobenzyl)(methyl)(oxo)-λ6-sulfaneylidene)-3-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorobenzyl)(methyl)(oxo)-λ6-sulfancylidone)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)picolinamide; N-((2-fluorobenzyl)(methyl)(oxo)-′./6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrazine-2-carboxamide; N-((2-fluorobenzyl)(methyl)(oxo)-λ6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-((2-fluorobenzyl)(methyl)(oxo)-X6-sulfaneylidene)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide; N-((2-fluorobenzyl)(oxo)(trifluoromethyl)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorophenyl)(methyl)(oxo)-X6-sulfaneylidene)-2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorphenyl)(methyl)(oxo)-λ6-sulfancylidene)-3-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-fluorophenyl)(methyl)(oxo)-X6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((2-fluorophenyl)(methyl)(oxo)-X6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrazine-2-carboxamide; N-((2-fluorophenyl)(methyl)(oxo)-λ6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-((2-fluorophenyl)(methyl)(oxo)-′./6-sulfaneylidene)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide; N-((2-fluorophenyl)(oxo)(trifluoromethyl)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-methoxyethyl)(methyl)(oxo)-′./6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((2-methoxyethyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-methoxyethyl)sulfonyl)-N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((2-methoxyphenyl)(methyl)(oxo)-λ6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((3-fluorophenyl)(methyl)(oxo)-′./6-sulfaneylidene)-4-((5-(trifluoromethyl)-_1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((3-fluoropyridin-4-yl)(methyl)(oxo)-‘//’-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((3-methoxyphenyl)(methyl)(oxo)-λ6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((3-methoxypyridin-4-yl)(methyl)(oxo)-X6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((4-(difluoromethyl)phenyl)(methyl)(oxo)-′./6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorophenyl)(cyclopropyl methyl)(oxo)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorophenyl)(methyl)(oxo)-′./6-sulfaneylidene)-2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorophenyl)(methyl)(oxo)-′./6-sulfancylidene)-2-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorophenyl)(methyl)(oxo)-λ6-sulfaneylidene)-3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorophenyl)(methyl)(oxo)-‘//’-sulfaneylidene)-3-methoxy-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-chlorophenyl)(methyl)(oxo)-′./6-sulfaneylidene)-5-(5-(trifluoromethyl)-K2,4-oxadiazol-3-yl)picolinamide; N-((4-chlorophenyl)(methyl)(oxo)-′./6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrazine-2-carboxamide; N-((4-chlorophenyl)(methyl)(oxo)-‘//’-sulfaneylidene)-5-(5-(trifluoromethyl)-_1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-((4-chlorophenyl)(methyl)(oxo)-‘//’-sulfaneylidene)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide; N-((4-chlorophenyl)(oxo)(trifluoromethyl)-′./6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((4-fluoro-2-methoxyphenyl)(methyl)(oxo)-λ6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((4-fluorophenyl)(methyl)(oxo)-′./6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((4-fluorophenyl)(methyl)(oxo)-‘//’-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-((4-methoxyphenyl)(methyl)(oxo)-λ6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((4-methoxyphenyl)(methyl)(oxo)-′./6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrazine-2-carboxamide; N-((4-methoxyphenyl)(methyl)(oxo)-′./6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-((4-methoxyphenyl)(methyl)(oxo)-′./6-sulfaneylidene)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide; N-((4-methoxyphenyl)(oxo)(trifluoromethyl)-′./6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((cyclobutyl methyl)(methyl)(oxo)-λ6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((cyclobutylmethyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((cyclobutylmethyl)sulfonyl)-N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((cyclopentylmethyl)(methyl)(oxo)-X6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((cyclopropylmethyl)(2-fluorobenzyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((cyclopropyl methyl)(2-fluorophenyl)(oxo)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((cyclopropylmethyl)(4-methoxyphenyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((cyclopropylmethyl)(methyl)(oxo)-X6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-((cyclopropyl methyl)(oxo)(pyridin-2-yl)-X6-sulfancylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((cyclopropyl methyl)(oxo)(pyridin-4-yl)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((oxetan-3-ylmethyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((perfluoroethyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(1-oxido-λ6-thietan-1-ylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(1-oxidotetrahydro-‘//’-thiophen-1-ylene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(1-oxidotetrahydro-2H-X6-thiopyran-1-ylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(4-oxido-1,4X6-oxathian-4-ylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(4-oxido-1,4X6-oxathian-4-ylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrazine-2-carboxamide; N-(4-oxido-1,4X6-oxathian-4-ylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-(4-oxo-1,4λ6-oxathian-4-ylidene)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide; N-(allyl(methyl)(oxo)-λ6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(allylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(allylsulfonyl)-N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(cyclopentyl(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(cyclopropyl(methyl)(oxo)-λ6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(cyclopropyl(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(cyclopropylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(ethylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isobutyl(methyl)(oxo)-X6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(isobutyl(methyl)(oxo)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isobutylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isobutylsulfonyl)-N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isopropyl(methyl)(oxo)-X6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(isopropylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-λ6-sulfaneylidene)cyclobutanecarboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′./6-sulfancylidene)cyclohexanecarboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′./6-sulfaneylidene)cycloheptanecarboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′./6-sulfancylidene) furan-3-carboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′./6-sulfanylidene)oxazole-5-carboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′./6-sulfaneylidene)picolinamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′./6-sulfaneylidene)pyrimidine-2-carboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-.6′-sulfancylidene)pyrimidine-4-carboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′./6-sulfanylidene)thiazole-5-carboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-′./6-sulfancylidene)thiophene-2-carboxamide; N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl (phenyl)-′./6-sulfaneylidene)thiophene-3-carboxamide; N-(methyl(oxo)(perfluoroethyl)-X6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(methyl(oxo)(phenyl)-X6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-(methyl(oxo)(prop-2-yn-1-yl)-X6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methylbenzamide; N-(methyl(oxo)(prop-2-yn-1-yl)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(propyl)-λ6-sulfanylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(methyl(oxo)(pyridin-2-yl)-λ6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(methyl(oxo)(pyridin-2-yl)-X6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrazine-2-carboxamide; N-(methyl(oxo)(pyridin-2-yl)-X6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-(methyl(oxo)(pyridin-2-yl)-X6-sulfaneylidene)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide; N-(methyl(oxo)(pyridin-3-yl)-λ6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-ylmethyl)benzamide; N-(methyl(oxo)(pyridin-4-yl)-λ6-sulfanylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(methyl(oxo)(pyridin-4-yl)-X6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)picolinamide; N-(methyl(oxo)(pyridin-4-yl)-X6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrazine-2-carboxamide; N-(methyl(oxo)(pyridin-4-yl)-′/.6-sulfanylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)pyrimidine-2-carboxamide; N-(methyl(oxo)(pyridin-4-yl)-λ6-sulfaneylidene)-6-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)nicotinamide; N-(methyl(oxo)(pyrimidin-2-yl)-′/.6-sulfaneylidene)-4-((5-(trifluromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(methyl(oxo)(pyrimidin-4-yl)-X6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(methyl(oxo)(trifluoromethyl)-X6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide; N-(oxo(pyridin-2-yl)(trifluoromethyl)-′/.6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-((oxo(pyridin-4-yl)(trifluoromethyl)-λ6-sulfaneylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(prop-2-yn-1-ylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-(propylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)-N-((trifluoromethyl)sulfonyl)benzamide; N-methyl-N-(((1-methylazetidin-3-yl)methyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-methyl-N-((oxetan-3-ylmethyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-methyl-N-((perfluoroethyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; N-methyl-N-(prop-2-yn-1-ylsulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide; phenyl(trifluoromethyl) ((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)biphenyl)imido)-′/.6-sulfanone; and pyridin-2-yl(trifluoromethyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-X6-sulfanone.
  • The present invention also relates to intermediates useful in the preparation of the compounds of Formula I. Such intermediates include but are not limited to 1a and 1b;
  • Figure US20220169621A1-20220602-C00006
  • wherein L1, A, L2, R10 are as defined herein before.
  • The present invention relates to a process for preparing the compound claimed in claim 1.
  • The process of the present invention comprises one or more steps selected from a to p depending upon the definition of L2.
  • In step (a), a compound of formula 1 is esterified into a compound of formula 2 using suitable esterifying reactant and reagent:
  • Figure US20220169621A1-20220602-C00007
  • In step (b), the compound of formula 2 by reacting with hydroxyl amine hydrochloride in the presence of suitable base is converted into a compound of formula 3 or the compound of formula 1 by reacting with hydroxyl amine is converted into a compound of formula 3′:
  • Figure US20220169621A1-20220602-C00008
  • In step (c), the compound of formula 3 and a compound of formula 8 are cyclized to obtain a compound of formula 4 or the compound of formula 3′ and a compound of formula 8 are cyclized to obtain a compound of formula 5:
  • Figure US20220169621A1-20220602-C00009
  • In step (d), the compound of formula 4 is hydrolyzed into a compound of formula 5:
  • Figure US20220169621A1-20220602-C00010
  • In step (e), the compound of formula 5 and a compound of formula 6 are reacted to obtain the compound of formula I:
  • Figure US20220169621A1-20220602-C00011
      • wherein, L2 is
  • Figure US20220169621A1-20220602-C00012
      •  an expression “#” on the left side indicates the point of attachment to A, and an expression “*” on the right side indicates the point of attachment to R10.
  • In step (f), a compound of formula 6 is reacted with a compound of formula 7 to obtain a compound of formula 1a:
  • Figure US20220169621A1-20220602-C00013
      • wherein, L2 is
  • Figure US20220169621A1-20220602-C00014
      •  an expression “#” on the left side indicates the point of attachment to A, and an expression “*” on the right side indicates the point of attachment to R10.
  • In step (g), the compound of formula 1a by reacting with hydroxyl amine hydrochloride is converted into a compound of formula 1b:
  • Figure US20220169621A1-20220602-C00015
      • wherein, L2 steps f to is
  • Figure US20220169621A1-20220602-C00016
      •  an expression “#” on the left side indicates the point of attachment to A, and an expression “*” on the right side indicates the point of attachment to R10.
  • In step (h), the compound of formula 1b and a compound of formula 8 are cyclized to obtain a compound of formula I:
  • Figure US20220169621A1-20220602-C00017
      • wherein, L2 is
  • Figure US20220169621A1-20220602-C00018
      •  an expression “#” on the left side indicates the point of attachment to A, and an expression “*” on the right side indicates the point of attachment to R10.
  • in step (i), a compound of formula 9 is reacted with ammonium carbamate to obtain a compound of formula 10:
  • Figure US20220169621A1-20220602-C00019
  • In step (j), the compound of formula 10 is reacted with a compound of formula 11 to obtain a compound of formula 1a:
  • Figure US20220169621A1-20220602-C00020
      • wherein, L2 is
  • Figure US20220169621A1-20220602-C00021
      •  an expression “#” on the left side indicates the point of attachment to A, and an expression “*” on the right side indicates the point of attachment to R10.
  • In step (k), the compound of formula 1a is reacted with hydroxyl amine hydrochloride to obtain a compound of formula 1b:
  • Figure US20220169621A1-20220602-C00022
      • wherein, L2 is
  • Figure US20220169621A1-20220602-C00023
      •  an expression “#” on the left side indicates the point of attachment to A, and an expression “*” on the right side indicates the point of attachment to R10.
  • In step (l), the compound of formula 1b and the compound of formula 8 are cyclized to obtain the compound of formula I:
  • Figure US20220169621A1-20220602-C00024
      • wherein, L2 is
  • Figure US20220169621A1-20220602-C00025
      •  an expression “#” on the left side indicates the point of attachment to A, and an expression “*” on the right side indicates the point of attachment to R10.
  • In step (m), the compound of formula 9 is imidized to obtain a compound of formula 11:
  • Figure US20220169621A1-20220602-C00026
  • In step (n), the compound of formula 11 is cyclized with the compound of formula 8 to obtain a compound of formula 12:
  • Figure US20220169621A1-20220602-C00027
  • In step (o), the compound of formula 12 is reacted with ammonium carbamate to obtain a compound of formula 13:
  • Figure US20220169621A1-20220602-C00028
  • In step (p), the compound of formula 13 is reacted with a compound of formula 14 to obtain the compound of formula I:
  • Figure US20220169621A1-20220602-C00029
      • wherein, L2 is
  • Figure US20220169621A1-20220602-C00030
      •  an expression “#” on the left side indicates the point of attachment to A, and an expression “*” on the right side indicates the point of attachment to R10.
  • Compound/s of the present invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compound/s of the present invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.
  • An anion part of the salt in case the compound/s of Formula I is a cationic or capable of forming a cation can be inorganic or organic. Alternatively, a cation part of the salt in case the compound/s of Formula I is an anionic or capable of forming anion can be inorganic or organic. Examples of inorganic anion part of the salt include but are not limited to chloride, bromide, iodide, fluoride, sulfate, phosphate, nitrate, nitrite, hydrogen carbonates, hydrogen sulfate. Examples of organic anion part of the salt include but are not limited to formate, alkanoates, carbonates, acetates, trifluoroacetate, trichloroacetate, propionate, glycolate, thiocyanate, lactate, succinate, malate, citrates, benzoates, cinnamates, oxalates, alkylsulphates, alkylsulphonates, arylsulphonates aryldisulphonates, alkylphosphonates, arylphosphonates, aryldiphosphonates, p-toluenesulphonate, and salicylate. Examples of inorganic cation part of the salt include but are not limited to alkali and alkaline earth metals. Examples of organic cation part of the salt include but are not limited to pyridine, methyl amine, imidazole, benzimidazole, hitidine, phosphazene, tetramethyl ammonium, tetrabutylammonium, choline and trimethylamine.
  • Metal ions in metal complexes of the compound/s of Formula I are especially the ions of the elements of the second main group, especially calcium and magnesium, of the third and fourth main group, especially aluminium, tin and lead, and also of the first to eighth transition groups, especially chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Particular preference is given to the metal ions of the elements of the fourth period and the first to eighth transition groups. Here, the metals can be present in the various valencies that they can assume.
  • Compound/s selected from Formula I, (including all stereoisomers, N-oxides, and salts thereof), typically may exist in more than one form. Formula I thus includes all crystalline and non-crystalline forms of the compound/s that Formula I represents. Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types). The term “polymorph” refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due to the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound represented by Formula I can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound represented by Formula I. Preparation and isolation of a particular polymorph of a compound represented by Formula I can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.
  • In another embodiment the present invention relates to a composition comprising the compound/s of Formula I agriculturally acceptable salts, metal complexes, constitutional isomers, stereo-isomers, diastereoisomers, enantiomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, geometric isomers, or N-oxides thereof optionally with one or more additional active ingredient with the auxiliary such as inert carrier or any other essential ingredient such as surfactants, additives, solid diluents and liquid diluents.
  • The compound/s of Formula I and the compositions according to the invention, respectively, are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.
  • The compound/s of Formula I and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e. g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants. Particularly, the compound/s of Formula I and the compositions according to the invention are important in the control of phytopathogenic fungi on soybeans and on the plant propagation material, such as seeds, and the crop material of soybeans. Accordingly, the present invention also includes a composition comprising at least one compound of Formula I and seed. The amount of the compound/s of Formula I in the composition ranges from 0.1 gai (gram per active ingredient) to 10 kgai (kilogram per active ingredient) per 100 kg of seeds.
  • Preferably, compound/s of Formula I and compositions thereof, respectively are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • The term “plant propagation material” is to be understood to denote all the generative or reproductive parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (c. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts, twigs, flowers, and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil.
  • These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
  • Preferably, treatment of plant propagation materials with compound/s of Formula I and compositions thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
  • The term “cultivated plants” is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://cera-gmc.org/, see GM crop database therein). Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties. Plants that have been modified by breeding, mutagenesis or genetic engineering, e. g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, IIPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g. tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady (glyphosate-tolerant, Monsanto, U.S.A.), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate-tolerant, Bayer CropScience, Germany).
  • Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as δ-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CrylIA(b), CrylIIA, CrylIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1, VIP2, VIP3 or VIP3A; insecticidal 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); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO02/015701). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP374753, WO93/007278, WO95/34656, EP427 529, EP451 878, WO03/18810 and WO03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the CrylAb toxin), YieldGard® Plus (corn cultivars producing CrylAb and Cry3Bbl toxins), Starlink® (com cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Abl, Cry35Abl and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the CrylAc toxin), Bollgard® I (cotton cultivars producing the Cryl Ac toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VTPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Btl 1 (e. g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bbl toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cryl F toxin and PAT enzyme).
  • Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called “pathogenesis-related proteins”
  • (PR proteins, see, e. g. EP392225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.
  • Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape, DOW Agro Sciences, Canada).
  • Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany).
  • The present invention also relates to a method for controlling or preventing infestation of plants by phytopathogenic micro-organisms in agricultural crops and or horticultural crops wherein an effective amount of at least one compound of formula I or the combination of the present invention or the composition of the present invention, is applied to the seeds of plants. The compound/s, combination/s and composition/s of the present invention can be used for controlling or preventing plant diseases. The compound/s of Formula I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:
  • Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. candida) and sunflowers (e. g. A. tragopogonis); Altemaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassicola or brassicae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A. alternata), tomatoes (e. g. A. solani or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A. tritici (anthracnose) on wheat and A. hordei on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northern leaf blight (B. zeicola) on corn, e. g. spot blotch (6. sorokiniana) on cereals and e. g. B. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e. g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuceliana: grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spots) on corn (e. g. Gray leaf spot: C. zeae-maydis), rice, sugar beets (e. g. C. beticola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum: leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e. g. C. sativus, anamorph: B. sorokiniana) and rice (e. g. C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e. g. C. gossypii), corn (e. g. C. graminicola: Anthracnose stalk rot), soft fruits, potatoes (e. g. C. coccodes: black dot), beans (e. g. C. lindemuthianum) and soybeans (e. g. C. truncatum or C. gloeosporioides); Corticium spp., e. g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cycloconium spp., e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C. liriodendri, teleomorph: Neonectria liriodendri: Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D. phaseolorum (damping off) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis: tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (£. pyri), soft fruits (£. veneta: anthracnose) and vines (£. ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets (£. betae), vegetables (e. g. E. pisi), such as cucurbits (e. g. E. cichoracearum), cabbages, rape (e. g. E. cruciferarum); Eutypa lata (Eutypa canker or diehack, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E. turcicum); Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e. g. wheat or barley), F. oxysporum on tomatoes, F. solani (f. sp. glycines now syn. F. virguliforme) and F. tucumaniae and F. brasiliense each causing sudden death syndrome on soybeans, and F. verticillioides on corn; Gaeumannomyces graminis (take-all) on cereals (e. g. wheat or barley) and corn; Gibberella spp. on cereals (e. g. G. feae) and rice (e. g. G. fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., e. g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseoli) (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P. parasitica), onions (e. g. P. destructor), tobacco (P. tabacina) and soybeans (e. g. P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e. g. on vines (e. g. P. tracheiphila and P. tetraspora) and soybeans (e. g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P. megasperma, syn. P. sojae), soybeans, potatoes and tomatoes (e. g. P. infestans: late blight) and broad-leaved trees (e. g. P. ramorum: sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara spp., e. g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers; Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples; Polymyxa spp., e. g. on cereals, such as barley and wheat (P. graminis) and sugar beets (P. betae) and thereby transmitted viral diseases; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapesia yallundae) on cereals, e. g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e. g. P. cubensis on cucurbits or P. humili on hop; Pseudopezicula tracheiphila (red fire disease or .rotbrenner’, anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P. asparagi on asparagus; Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P. teres (net blotch) on barley; Pyricularia spp., e. g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. rolfsii or S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum (Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines; Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S. reiliana: head smut), sorghum and sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn. Chalara elegans); Tilletia spp. (common bunt or stinking smut) on cereals, such as e. g. T. tritici (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incamata (grey snow mold) on barley or wheat; Urocystis spp., e. g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e. g. U. appendiculatus, syn. U. phaseoli) and sugar beets (e. g. U. betae); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae), corn (e. g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (e. g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e. g. V. dahliae on strawberries, rape, potatoes and tomatoes.
  • The compounds of formula I, the combinations or the compositions thereof may be used to treat several fungal pathogens. Non-limiting examples of pathogens of fungal diseases which can be treated in accordance with the invention include:
  • Ustilaginales such as Ustilaginoidect vireos, Ustilago nuda, Ustilago tritici, Ustilago zeae, rusts for example those caused by Pucciniales such as Cerotelium fid, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp. Hordei, Puccinia striiformis f.sp. Secalis, Pucciniastrum coryli, or Uredinales such as Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor and Uromyces viciae-fabae; and other rots and diseases such as those caused by Cryptococcus spp., Exobasidium vexans, Marasrniellus inoderma, Mycena spp., Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani, Thanetephorus cucurnzeris, Entyloma dahliae, Entylonzella nzicrospora, Neovossia nzoliniae and Tilletia caries. Blastocladiomycetes, such as Physoderma maydis. Mucoromycetes, such as Choanephora cucurbitarum; Mucor spp.; and Rhizopus arrhizus,
  • In another embodiment diseases caused by rust disease pathogens, for example Gymnospomngium species, for example Gymnospomngium sabinae, Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae\ Puccinia species, for example Puccinia recondita, Puccinia graminis oder Puccinia strif ormis; Uromyces species, for example Uromyces appendiculatus;
  • In particular, Cronartium ribicola (White pine blister rust); Gymnospomngium juniperi-virginianae (Cedar-apple rust); Hemileia vastatrix (Coffee rust); Phakopsora meibomiae and P. pachyrhizi (Soybean rust); Puccinia coronata (Crown Rust of Oats and Ryegrass); Puccinia graminis (Stem rust of wheat and Kentucky bluegrass, or black rust of cereals); Puccinia hemerocallidis (Daylily rust); Puccinia persistens subsp. triticina (wheat rust or ‘brown or red rust’); Puccinia sorghi (rust in corn); Puccinia strilformis (‘Yellow rust’ in cereals); Uromyces appendiculatus (rust of beans); Uromyces phaseoli (Bean rust); Puccinia melanocephata (‘Brown rust’ in sugarcane); Puccinia kuehnii (‘Orange rust’ in sugarcane).
  • Plants which can be treated in accordance with the invention include the following: cotton, flax, grapevine, fruits, vegetables, such as Rosaceae sp (for example pome fruits such as apples, pears, apricots, cherries, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example banana trees and plantations), Rubiaceae sp. (for example coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example lemons, oranges and grapefruit); Vitaceae sp. (for example grapes); Solanaceae sp. (for example tomatoes, peppers), Liljaceae sp., Asteraceae sp. (for example lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceae sp. (for example leek, onion), Papilionaceae sp. (for example peas); major crop plants, such as Poaceae/Gramineae sp. (for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (for example sunflower), Brassicaceae sp. (for example white cabbage, red cabbage, broccoli, cauliflower, Bmssels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress), Fabacae sp. (for example bean, peanuts), Papilionaceae sp. (for example soya bean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example sugar beet, fodder beet, swiss chard, beetroot); Malvaceae (for example cotton); useful plants and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants.
  • More preference is given to controlling the following diseases of soya beans: Fungal diseases on leaves, stems, pods and seeds caused, for example, by Altemaria leaf spot (Altemaria spec. atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), cercospora leaf spot and blight (Cercospora kikuchii), choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), drechslera blight (Drechslera glycini) frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), target spot (Corynespora cassiicola).
  • Fungal diseases on roots and the stem base caused, for example, by black root rot (Calonectiia crotalariae), charcoal rot (Macrophomina phaseolina), fusarium blight or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmospora vasinfecta), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), phytophthora rot (Phytophthora nzegaspertzza), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), Sclerotinia southern blight (Sclerotinia roffsii), thielaviopsis root rot (Thielaviopsis basicola).
  • The present invention also relates to the use of compounds of formula 1, the combinations or the compositions thereof for controlling or preventing the following plant diseases: Puccinia spp. (rusts) on various plants, for example, but not limited to P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye and Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans, Ilemileia vastatrix (Coffee rust), Uromyces appendiculatus, Uromyces fabae and Uromyces phaseoli (rust of beans).
  • The present invention further relates to the use of compounds of formula I, the combinations or the compositions thereof for controlling or preventing against phytopathogenic fungi such as Phakopsora pachyrhizi, Phakopsora meibomiae, of agricultural crops and or horticultural crops.
  • The compounds of Formula I, the combinations and the compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials. The term “protection of materials” is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria.
  • As to the protection of wood and other materials, the particular attention is paid to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichuras spp.; Basidiomycetes such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Porl′a spp., Serpula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Altemaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.
  • In one embodiment the compound/s of Formula I, the combinations and the compositions thereof, respectively, are particularly suitable for controlling the following plant diseases: Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.
  • The present invention further relates to a method for controlling or preventing phytopathogenic fungi. The method comprises treating the fungi or the materials, plants, plant parts, locus thereof, soil or seeds to be protected against fungal attack, with an effective amount of at least one compound of Formula I or the combinations or the compositions comprising at least one compound of Formula I.
  • The method of treatment according to the invention can also be used in the field of protecting stored products or harvest against attack of fungi and microorganisms. According to the present invention, the term “stored products” is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired. Stored products of crop plant origin, such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted, which process is also known as post-harvest treatment. Also falling under the definition of stored products is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood. Stored products of animal origin are hides, leather, furs, hairs and the like. The combinations according the present invention can prevent disadvantageous effects such as decay, discoloration or mold. Preferably “stored products” is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.
  • The compound/s of Formula I, the combinations and the compositions thereof, respectively, may be used for improving the health of a plant. The invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of compound/s I and compositions thereof, respectively.
  • The term “plant health” is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves (“greening effect”)), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress. The above identified indicators for the health condition of a plant may be interdependent or may result from each other.
  • The compound/s of Formula I can be present in different crystal modifications or polymorphs whose biological activity may differ. They are likewise subject matter of the present invention.
  • The compound/s of Formula I are employed as such or in the form of compositions for treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.
  • Plant propagation materials may be treated with compound/s of Formula I, the combinations and the compositions thereof protectively either at or before planting or transplanting.
  • The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of Formula I.
  • An agrochemical composition comprises a fungicidally effective amount of a compound of Formula I. The term “effective amount” denotes an amount of the composition or of the compound/s of Formula I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound of Formula I used.
  • The compound/s of Formula I, their oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e. g. BR, TB, DT), granules (e. g. WG, SG, GR, FG, GG, MG), insecticidal articles (e. g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e. g. GF). These and further compositions types are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, eh Ed. May 2008, CropLife International.
  • The compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e. g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e. g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e. g. cyclohexanone; esters, e. g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e. g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof. Suitable solid carriers or fillers are mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e. g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates,N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.
  • Suitable cationic surfactants are quaternary surfactants, for ex ample quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines.
  • Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compounds of Formula I on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (c. g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants (e. g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (c. g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e. g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • Examples for composition types and their preparation are:
  • i) Water-Soluble Concentrates (SL, LS)
  • 10-60 wt % of a compound of Formula I and 5-15 wt % wetting agent (e. g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e. g. alcohols) ad 100 wt %. The active substance dissolves upon dilution with water.
  • ii) Dispersible Concentrates (DC)
  • 5-25 wt % of a compound of Formula I and 1-10 wt % dispersant (e. g. polyvinyl pyrrolidone) are dissolved in organic solvent (c. g. cyclohexanone) ad 100 wt %. Dilution with water gives a dispersion.
  • iii) Emulsifiable Concentrates (EC)
  • 15-70 wt % of a compound of Formula I and 5-10 wt % emulsifiers (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (c. g. aromatic hydrocarbon) ad 100 wt %. Dilution with water gives an emulsion.
  • iv) Emulsions (EW, EO, ES)
  • 5-40 wt % of a compound of Formula I and 1-10 wt % emulsifiers (c. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt % water-insoluble organic solvent (e. g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt % by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
  • v) Suspensions (SC, OD, FS)
  • In an agitated ball mill, 20-60 wt % of a compound of Formula I are comminuted with addition of 2-10 wt % dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate), 0.1-2 wt % thickener (e. g. xanthan gum) and water ad 100 wt % to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt % hinder (e. g. polyvinyl alcohol) is added.
  • vi) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)
  • 50-80 wt % of a compound of Formula I are ground finely with addition of dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt % and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance. vii) Water-dispersible powders and water-soluble powders (WP, SP, WS) 50-80 wt % of a compound of Formula I are ground in a rotor-stator mill with addition of 1-5 wt % dispersants (e. g. sodium lignosulfonate), 1-3 wt % wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g. silica gel) ad 100 wt %. Dilution with water gives a stable dispersion or solution of the active substance.
  • viii) Gel (GW, GF)
  • In an agitated ball mill, 5-25 wt % of a compound of Formula I are comminuted with addition of 3-10 wt % dispersants (e. g. sodium lignosulfonate), 1-5 wt % thickener (e. g. carboxymethyl cellulose) and water ad 100 wt % to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
  • ix) Microemulsion (ME)
  • 5-20 wt % of a compound of Formula I are added to 5-30 wt % organic solvent blend (e. g. fatty acid dimethyl amide and cyclohexanone), 10-25 wt % surfactant blend (e. g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100%. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
  • x) Microcapsules (CS)
  • An oil phase comprising 5-50 wt % of a compound of Formula I, 0-40 wt % water insoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt % acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt % of a compound of Formula I according to the invention, 0-40 wt % water insoluble organic solvent (e. g. aromatic hydrocarbon), and an isocyanate monomer (c. g. diphenylmethene-4,4′-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). The addition of a poly amine (e. g. hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1-10 wt %. The wt % relate to the total CS composition.
  • xi) Dustable Powders (DP, DS)
  • 1-10 wt % of a compound of Formula 1 are ground finely and mixed intimately with solid carrier (e. g. finely divided kaolin) ad 100 wt %.
  • xii) Granules (GR, FG)
  • 0.5-30 wt % of a compound of Formula I are ground finely and associated with solid carrier (e. g. silicate) ad 100 wt %. Granulation is achieved by extrusion, spray-drying or fluidized bed.
  • xiii) Ultra-Low Volume Liquids (UL)
  • 1-50 wt % of a compound of Formula I are dissolved in organic solvent (e. g. aromatic hydrocarbon) ad 100 wt %.
  • The compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt % anti-freezing agents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt % colorants.
  • The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active ingredient (ai). The active ingredients (ai) are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • For the purposes of treatment of plant propagation materials, particularly seeds, solutions for seed treatment (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually employed. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations.
  • Application can be carried out before or during sowing. Methods for applying compound/s of Formula 1, the combinations and the compositions thereof, respectively, onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods. Preferably, compound/s of Formula I, the combinations and the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 1.0 kg per ha, and in particular from 0.1 to 1.0 kg per ha.
  • In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
  • When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
  • Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:20 to 20:1.
  • A pesticide is generally a chemical or biological agent (such as pesticidally active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease. The term “pesticide” includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.
  • The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful arca.
  • According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
  • Consequently, one embodiment of the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component 3) as defined herein.
  • The compound/s of Formula I, the combinations and the compositions thereof comprising them in the use as fungicides with other fungicides may result in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance development. Furthermore, in many cases, extraordinary effects are obtained.
  • The present invention also relates to the combination comprising at least one compound of Formula T and at least one further pesticidally active substance selected from the group of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertiliers and nutrients. The pesticidally active substances reported in WO2015 185485 pages 36-43 and WO2017093019 pages 42-56 can be used in conjunction with which the compound/s of Formula I.
  • The active substances referred to as component 2, their preparation and their activity e. g. against harmful fungi is known (cf: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by 1U PAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP141317; EP152031; EP226917; EP243970; EP256503; EP428941; EP532022; EP1028125; EP1035122; EP1201648; EP1122244, JP20023 16902; DE19650197; DE10021412; DE102005009458; U.S. Pat. Nos. 3,296,272; 3,325,503; WO9846608; WO9914187; WO9924413; WO9927783; WO0029404; WO0046148; WO0065913; WO0154501; WO 0156358; WO0222583; WO0240431; WO0310149; WO0311853; WO0314103; WO0316286; WO0353145; WO0361388; WO0366609; WO0374491; WO0449804; WO0483193; WO05 120234; WO05 123689; WO05 123690; WO0563721; WO0587772; WO0587773; WO0615866; WO0687325; WO0687343; WO0782098; WO0790624; WO1 1028657; WO2012168188; WO2007006670; WO201177514; WO13047749; WO10069882; WO13047441; WO0316303; WO0990181; WO13007767; WO1310862; WO13127704; WO13024009; WO13024010; WO13047441; WO13162072; WO13092224 and WOH135833.
  • The present invention furthermore relates to agrochemical mixtures comprising at least one compound of Formula I (component 1) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier. Furthermore, combating harmful fungi with a mixture of compound/s of Formula I and at least one fungicide from groups A) to K), as described above, is advantageous than combating those fungi with individual compound/s of Formula I or individual fungicides from groups A) to K).
  • By applying compounds of Formula I together with at least one pesticidally active substance from groups A) to O) an enhanced effect can be obtained.
  • This can be obtained by applying the compound/s of Formula I and at least one further pesticidally active substance simultaneously, either jointly (e. g. as tank-mix) or separately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further pesticidally active substance(s). The order of application is not essential for working of the present invention.
  • When applying compound/s of Formula I and a pesticidally active substance sequentially the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day. In the binary mixtures and compositions according to the invention the weight ratio of the component 1) and the component 2) generally depends from the properties of the active components used, usually it is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1, even more preferably in the range of 1:4 to 4:1 and in particular in the range of 1:2 to 2:1.
  • According to a further embodiment of the binary mixtures and compositions thereof, the weight ratio of the component 1) and the component 2) usually is in the range of 1000:1 to 1:1000, often in the range of 100:1 to 1:100, regularly in the range of 50:1 to 1:50, preferably in the range of 20:1 to 1:20, more preferably in the range of 10:1 to 1:10, even more preferably in the range of 4:1 to 1:4 and in particular in the range of 2:1 to 1:2.
  • In the ternary mixtures, i.e. compositions according to the invention comprising the component 1) and component 2) and a compound III (component 3), the weight ratio of component 1) and component 2) depends from the properties of the active substances used, usually it is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1 and in particular in the range of 1:4 to 4:1, and the weight ratio of component 1) and component 3) usually it is in the range of 1:100 to 100:1, regularly in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1 and in particular in the range of 1:4 to 4:1.
  • Any further active components are, if desired, added in a ratio of 20:1 to 1:20 to the component 1).
  • These ratios are also suitable for inventive mixtures applied by seed treatment.
  • The present invention also relates to a process for preparing the compound/s of the present invention. The process for preparing the compound/s of the present invention is described in the experimental section in more detail.
  • The invention disclosed in the present disclosure shall now be elaborated with the help of non-limiting schemes and examples.
    • CHEMISTRY EXAMPLES General Synthetic Scheme
  • Figure US20220169621A1-20220602-C00031
  • Figure US20220169621A1-20220602-C00032
  • Figure US20220169621A1-20220602-C00033
    • Example 1 Preparation of N42-fluorophenyl)(methyl)(oxo)-X6-sulfanylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide (Compound 3)
  • Figure US20220169621A1-20220602-C00034
    • Step-1: Methyl 4-cyanobenzoate
  • Figure US20220169621A1-20220602-C00035
  • To a stirred solution of 4-cyanobenzoic acid (25 g, 170 mmol) in v, A-dimethyl formamide (120 mL), potassium carbonate (35.2 g, 255 mmol) was added at 25° C. and cooled to 0° C. To the resulting reaction mixture, methyl iodide (15.9 mL, 255 mmol) was slowly added. The resulting reaction mixture was stirred at 45° C. for 2 h. After completion of the reaction, the reaction mixture was cooled to 25° C. and crushed ice was poured into it with stirring. Stirring was continued for 10 minutes to obtain a precipitate. The precipitate was filtered, washed with water and dried under reduced pressure to obtain methyl 4-cyanobenzoate (24.6 g, 153 mmol, 90% yield).
    • Step-2: Methyl-4-(N′-hydroxycarbamimidoyl)benzoate
  • Figure US20220169621A1-20220602-C00036
  • To a stirred solution of methyl 4-cyanobenzoate (0.9 g, 5.6 mmol) in methanol (12 mL), sodium bicarbonate (0.5 g, 6.1 mmol) and hydroxylamine hydrochloride (0.4 g, 5.6 mmol) were added. The resulting reaction mixture was heated to reflux for 4 h. After completion of the reaction, the reaction mixture was cooled to 25° C. and filtered. The filtrate was concentrated under reduced pressure to obtain methyl-4-(N-hydroxycarbamimidoyl)benzoate (0.9 g, 4.6 mmol, 83% yield).
    • Step-3: Methyl 4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoate
  • Figure US20220169621A1-20220602-C00037
  • To a stirred solution of methyl-4-(N-hydroxycarbamimidoyl)benzoate (0.9 g, 4.6 mmol) in tetrahydrofuran (10 mL), trifluoroacetic anhydride (1.0 mL, 7 0 mmol) was added at 0 under nitrogen atmosphere. The resulting reaction mixture was stirred at 25° C. for 16 h and diluted with ethyl acetate (30 mL). Ethyl acetate layer was washed three times with aq. sat. Sodium bicarbonate (30 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude residue was purified by column chromatography (eluent 0-30% ethyl acetate in hexane) on silica gel to obtain methyl 4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoate (0.6 g, 2.0 mmol, 44% yield).
    • Step 4: 4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid
  • Figure US20220169621A1-20220602-C00038
  • To a stirred solution of methyl 4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoate (15 g, 55.1 mmol) in tetrahydrofuran (120 mL), a solution of sodium hydroxide (4.0 g, 99 mmol) in water (30 mL) was added dropwise by a dropping funnel at 0° C. The resulting reaction mixture was stirred for 16 h at 25° C. After completion of the reaction, the solvent was removed by evaporation under reduced pressure. Water (50 mL) was added to the residue and cooled to 0° C. and acidified to pH 3 with 3N aqueous hydrochloric acid. The precipitate was collected by filtration, washed with water, and dried to obtain 4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid (11.2 g, 43.4 mmol, 79% yield).
    • Step-5 (2-fluorophenyl)(methyl)sulfane
  • Figure US20220169621A1-20220602-C00039
  • To a stirred solution of 2-fluorobenzenethiol (2.7 g, 21.07 mmol) in acetonitrile (20 mL), potassium carbonate (7.3 g, 52.7 mmol) was added at 0° C. Ice bath was removed and the reaction mixture was stirred for 30 min at 25° C. The reaction mixture was cooled again to 0° C. and methyl iodide (1.6 mL, 25.3 mmol) was added slowly. The reaction mixture was stirred at 25° C. for 4 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (40 mL) and washed three times with water (15 mL). The ethyl acetate layer was separated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain (2-fluorophenyl)(methyl)sulfane (2.2 g, 15.5 mmol, 73% yield). The crude product was used as such in the next step without purification.
    • Step-6: (2-Fluorophenyl)(imino)(methyl)-X6-sulfanone
  • Figure US20220169621A1-20220602-C00040
  • To a stirred solution of (2-fluorophenyl)(methyl)sulfane (2.7 g, 19.0 mmol) in methanol (38.0 mL), was added ammonium carbamate (3.26 g, 41.8 mmol). Then diacetoxy iodobenzene (13.5 g, 41.8 mmol) was slowly added portion wise at 0° C. The resulting reaction was stirred at 25° C. for 12 h. After completion of the reaction, methanol was evaporated under reduced pressure, diluted with ethyl acetate (60 mL) and washed with water (20 mL). The ethyl acetate layer was washed two times with aq. saturated sodium bicarbonate solution (20 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude residue was purified using column chromatography on silica gel to obtain (2-fluorophenyl)(imino)(methyl)-′/.6-sulfanone (2.0 g, 11.6 mmol, 61% yield).
    • Step 7: Preparation of N-((2-fluorophenyl)(methyl)(oxo)-/.6-sulfanylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide (Compound 3)
  • Figure US20220169621A1-20220602-C00041
  • To a stirred solution of 4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid (0.5 g, 1.9 mmol) in dry dichloromethane (10 mL), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.7 g, 3.9 mmol) and 4-dimethylaminopyridine (0.7 g, 5 8 mmol) were added at 5° C. under nitrogen atmosphere. Then (2-fluorophenyl)(imino)(methyl)-′/.6-sulfanone (0.5 g, 3.0 mmol) was added, and the reaction mixture was stirred at 25° C. for 16 h. After completion of the reaction, product was extracted by dichloromethane (30 mL). The dichloromethane layer was washed two times with brine solution (10 mL), dried over anhydrous sodium sulphate and concentrated. The residue was purified by column chromatography on silica gel using hexane to 60% ethyl acetate in hexane as an eluent to obtain N-((2-fluorophenyl)(metho)(oxo)-‘//’sulfanylidene)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide (0.1 g, 0.3 mmol, 16% yield).
  • TABLE NO 1
    The following compounds were prepared by the procedure analogous to that of the
    Compound 3 using appropriate starting materials.
    Compound
    No. IUPAC Name Structure Yield
    1 N-((4- chlorophenyl)(methyl)(oxo)- λ6-sulfanylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00042
         		0.7 g, 53.0% yield
    2 N-(methyl(oxo)(pyridin-2- yl)-λ6-sulfanylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00043
         		0.4 g, 46.0% yield
    4 N-(methyl(oxo)(pyridin-4- yl)-λ6-sulfanylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00044
         		0.1 g, 15.0% yield
    5 N-((3- fluorophenyl)(methyl)(oxo)- λ6-sulfanylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00045
         		0.1 g, 18.0% yield
    6 N-((4- fluorophenyl)(methyl)(oxo)- λ6-sulfanylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00046
         		0.4 g, 50.0% yield
    7 N-(methyl(oxo)(4- (trifluoromethyl)phenyl)-λ6- sulfanylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00047
         		0.3 g, 31.0% yield
    8 N-((4- bromophenyl)(methyl)(oxo)- λ6-sulfanylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00048
         		0.4 g, 45.0% yield
    9 N-(methyl(oxo)(phenyl)-λ6- sulfanylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00049
         		0.1 g, 27.0% yield
    10 N-((4- methoxyphenyl)(methyl)(oxo)- λ6-sulfanylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00050
         		0.1 g, 17.0% yield
    12 N-(methyl(oxo)(4- (trifluoromethoxy)phenyl)-λ6- sulfanylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00051
         		0.2 g, 17.0% yield
    30 N-(methyl(oxo)(p-tolyl)-λ6- sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00052
         		0.2 g, 20% yield
    31 N-((4- cyanobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00053
         		0.2 g, 45% yield
    32 N-((2,6- difluorobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00054
         		0.3 g, 50% yield
    33 N-((2,3- difluorobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00055
         		0.3 g, 65% yield
    34 N-((4- methoxybenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00056
         		0.3 g, 55% yield
    35 N-((4- bromobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00057
         		0.4 g, 62% yield
    36 N-((2,6- difluorophenyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00058
         		0.2 g, 31% yield
    37 N-((2,4- difluorobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00059
         		0.4 g, 69% yield
    38 N-((2- fluorobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00060
         		0.1 g, 40.1%
    39 N-((3- fluorobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00061
         		0.1 g, 26%
    40 N-(methyl(2- methylbenzyl)(oxo)-λ6- sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00062
         		0.2 g, 30%
    41 N-((3,5- dimethylphenyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00063
         		0.4 g, 72%
    42 N-((4- cyanophenyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00064
         		0.4 g, 71% yield
    43 N-(1-oxidotetrahydro-2H- 1λ6-thiopyran-1-ylidene)-4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00065
         		0.3 g, 62% yield
    44 N-(methyl(oxo)(m-tolyl)-λ6- sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00066
         		0.4 g, 83% yield
    45 N-(methyl(3- methylbenzyl)(oxo)-λ6- sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00067
         		0.2 g, 48%
    46 N-((3- methoxyphenyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00068
         		0.4 g, 76% yield
    47 N-((2,4- difluorophenyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00069
         		0.3 g, 59% yield
    48 N-(methyl(oxo)(thiazol-2-yl)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00070
         		0.3 g, 74% yield
    49 N-((4- fluorobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00071
         		0.3 g, 69% yield
    50 N-(methyl(oxo)(4- (trifluoromethyl)benzyl)-λ6- sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00072
         		0.3 g, 68% yield
    51 N-((2,6- dichlorobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00073
         		0.3 g, 54% yield
    52 N-(methyl(oxo)(pyridin-2- ylmethyl)-λ6-sulfaneylidene)- 4-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00074
         		0.1 g, 27% yield
    53 N-(methyl(4-methylthiazol-2- yl)(oxo)-λ6-sulfaneylidene)-4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00075
         		0.3 g, 63% yield
    54 N-(methyl(5-methyl-1,3,4- thiadiazol-2-yl)(oxo)-λ6- sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00076
         		0.3 g, 50% yield
    55 N-((2,5- dichlorophenyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00077
         		0.3 g, 62% yield
    56 N-((2,4- dimethoxyphenyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00078
         		0.4 g, 71% yield
    57 N-((3,4- difluorophenyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00079
         		0.3 g, 59% yield
    58 N-(4-oxido-1,4λ6-oxathian-4- ylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00080
         		0.3 g, 57% yield
    59 N-(methyl(oxo)(pyridin-4- ylmethyl)-λ6-sulfaneylidene)- 4-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00081
         		0.1 g, 29% yield
    60 N-((4- chlorobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00082
         		0.1 g, 31% yield
    61 N-((4-chloro-3- fluorobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00083
         		0.1 g, 30% yield
    62 N-((2,5- difluorobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00084
         		0.1 g, 16% yield
    63 N-((2- fluorophenyl)(methyl)(oxo)- λ6-sulfaneylidene)-3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00085
         		0.1 g, 17% yield
    64 N-(methyl(oxo)(4- (trifluoromethyl)phenyl)-λ6- sulfaneylidene)-3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00086
         		0.1 g, 18% yield
    65 N-((4- fluorophenyl)(methyl)(oxo)- λ6-sulfaneylidene)-3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00087
         		0.5 g, 78% yield
    66 N-(methyl(oxo)(pyridin-2- yl)-λ6-sulfaneylidene)-3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00088
         		0.2 g, 32% yield
    67 N-(methyl(oxo)(phenyl)-λ6- sulfaneylidene)-3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00089
         		0.4 g, 78% yield
    68 N-((2,6- difluorobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00090
         		0.3 g, 55% yield
    69 N-((2,4- difluorobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00091
         		0.3 g, 64% yield
    70 N-((4- methoxybenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00092
         		0.2 g, 40% yield
    71 N-((4- methoxyphenyl)(methyl)(oxo)- λ6-sulfaneylidene)-3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00093
         		0.4 g, 60% yield
    72 N-((2,6- difluorophenyl)(methyl)(oxo)- λ6-sulfaneylidene)-3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00094
         		0.4 g, 73% yield
    73 N-(methyl(oxo)(thiazol-2-yl)- λ6-sulfaneylidene)-3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00095
         		0.2 g, 51% yield
    74 N-(1-oxidotetrahydro-2H- 1λ6-thiopyran-1-ylidene)-3- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00096
         		0.1 g, 31% yield
    75 N-((4- cyanobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00097
         		0.3 g, 54% yield
    76 N-((4- fluorophenyl)(isopropyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00098
         		0.1 g, 37% yield
    77 N-(isopropyl(4- methoxyphenyl)(oxo)-λ6- sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00099
         		0.2 g, 39% yield
    78 N-((4- chlorophenyl)(isopropyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00100
         		0.2 g 43% yield
    79 N-(isopropyl(oxo)(pyridin-2- yl)-λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00101
         		0.3 g, 54% yield
    80 N-(isopropyl(oxo)(phenyl)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00102
         		0.3 g, 43% yield
    81 3-fluoro-N-((4- methoxyphenyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00103
         		0.4 g, 80% yield
    82 N-((3- bromophenyl)(ethyl)(oxo)-λ6- sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00104
         		0.3 g, 52% yield
    83 N-(methyl(oxo)(2- phenoxyethyl)-λ6- sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00105
         		0.2 g, 49% yield
    206 N-(allyl(methyl)(oxo)-λ6- sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00106
         		0.1 g, 22%
    207 N-(ethyl(methyl)(oxo)-λ6- sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00107
         		0.1 g, 15% yield
    208 N-((2- methoxyethyl)(methyl)(oxo)- λ6-sulfaneylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00108
         		0.3 g, 65% yield
    • Example-2: 2-fluorophenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-/.6-sulfanone (Compound 12)
  • Figure US20220169621A1-20220602-C00109
    • Step 1: 4-(((2-Fluorophenyl)(methyl)(oxo)-X6-sulfanylidene)amino)benzonitrile
  • Figure US20220169621A1-20220602-C00110
  • The reaction mixture containing 4-bromobenzonitrile (0.3 g, 1.6 mmol), (2-fluorophenyl)(imino)(methyl)-′.6-sulfanonc (0.3 g, 2.0 mmol) and cesium carbonate (0.8 g, 2.3 mmol) in toluene (10 mL) was purged with nitrogen for 10 minutes. The racemic BINAP (0.08 g, 0.12 mmol) and palladium(II) acetate (0.02 g, 0.08 mmol) were added and the reaction mixture was stirred at 105° C. for 18 h. After completion of the reaction, the reaction mixture was cooled to 25° C. and was extracted with ethyl acetate (30 mL), the ethyl acetate layer was washed by water (10 mL), dried over anhydrous sodium sulphate and concentrated. The crude product 4-(((2-fluorophenyl)(methyl)(oxo)-′/.6-sulfanylidene)amino)benzonitrile (0.5 g).
    • Step 2: 4-(((2-Fluorophenyl)(methyl)(oxo)-X6-sulfanylidene)amino)-N′-hydroxybenzimidamide
  • Figure US20220169621A1-20220602-C00111
  • To a stirred solution of 4-(({circumflex over ( )}-fluorophenyl)(methyl)(oxo)-λ6-sulfanylidene)amino)benzonitrile (0.5 g, 1.6 mmol) in ethanol (12 mL), sodium bicarbonate (0.2 g, 3 0 mmol) and hydroxylamine hydrochloride (0.2 g, 3.0 mmol) were added and stirred at 65° C. for 16 h. After completion of the reaction, the reaction mixture was cooled to 25° C. and filtered. The filtrate was concentrated to obtain a crude product (Z)-4-(((2-fluorophenyl)(methyl)(oxo)-h6-sulfanylidene)amino)-N′-hydroxybenzimidamide (0.5 g, 99%).
    • Step 3: (2-Fluorophenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)-λ6-sulfanone
  • Figure US20220169621A1-20220602-C00112
  • To a stirred solution of (Z)-4-(((2-fluorophenyl)(methyl)(oxo)-w6-sulfanylidene)amino)-N′-hydroxybenzimidamide (0.5 g, 1.6 mmol) in tetrahydrofuran (10 mL), trifluoroacetic anhydride (0.3 mL, 2.4 mmol) was added at 0° C. and stirred at 25° C. for 16 h. After completion of the reaction, the reaction mixture was filtered. The filtrate was concentrated to obtain the crude compound. The crude product was purified by column chromatography on silica gel using eluent hexane to 40% Ethyl acetate in hexane to obtain pure (2-fluorophenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyMmino)-L6-sulfanone (0.4 g, 60% yield).
  • TABLE NO 2
    The following compounds were prepared by the procedure analogous to that of the
    compound 12 using appropriate starting materials.
    Compound
    No. IUPAC Name Structure Yield
    13 (4-chlorophenyl)(methyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00113
         		0.39 g, 62.0% yield
    14 (3-fluorophenyl)(methyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00114
         		0.29 g, 48.0% yield
    15 methyl(pyridin-4-yl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6sulfanone
    Figure US20220169621A1-20220602-C00115
         		0.13 g, 22.0% yield
    16 methyl(pyridin-2-yl)((4-(5- (trifluoromethyl)isoxazol-3- yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00116
         		0.335 g, 56.0% yield
    17 (4-fluorophenyl)(methyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00117
         		198 mg, 45.0% yield
    18 methyl(phenyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00118
         		285 mg, 48.0% yield
    19 methyl((4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl)phenyl)imino)(4- (trifluoromethyl)phenyl)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00119
         		382 mg, 54.0% yield
    20 (4-methoxyphenyl)(methyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00120
         		414 mg, 64.0% yield
    21 methyl(4- (trifluoromethoxy)phenyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00121
         		373 mg, 55.0% yield
    84 (2,6-difluorophenyl)(methyl)((4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00122
         		0.2 g, 28% yield
    85 (2,6-difluorobenzyl)(methyl)((4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00123
         		0.3 g, 47% yield
    86 (2,4-difluorobenzyl)(methyl)((4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00124
         		0.2 g, 33% yield
    87 (2,3-difluorobenzyl)(methyl)((4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00125
         		0.2 g, 37% yield
    88 methyl(2-methylbenzyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00126
         		0.2 g, 36% yield
    89 (4-fluorobenzyl)(methyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00127
         		0.2 g, 34% yield
    90 methyl((4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl)phenyl)imino)(4- (trifluoromethyl)benzyl)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00128
         		0.3 g, 45% yield
    91 (2,6-dichlorobenzyl)(methyl)((4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00129
         		0.3 g, 47% yield
    92 (4-bromobenzyl)(methyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00130
         		0.2 g, 32% yield
    93 methyl(pyridin-2-ylmethyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00131
         		0.2 g, 42% yield
    94 (2-fluorobenzyl)(methyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00132
         		0.3 g, 27% yield
    95 (3-fluorobenzyl)(methyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00133
         		0.4 g, 41% yield
    96 (2,4- dimethoxyphenyl)(methyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00134
         		0.3 g, 50% yield
    97 (3,4-difluorophenyl)(methyl)((4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00135
         		0.4 g, 60% yield
    98 (4-chlorobenzyl)(methyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00136
         		0.1 g, 40% yield
    99 (4-chloro-3- fluorobenzyl)(methyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00137
         		0.1 g, 36% yield
    100 (4-methoxyphenyl)(methyl)((3-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00138
         		0.6 g, 81% yield
    101 (3-methoxyphenyl)(methyl)((3-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00139
         		0.5 g, 75% yield
    102 1-((3-(5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl)phenyl)imino)hexahydro-1λ6- thiopyran 1-oxide
    Figure US20220169621A1-20220602-C00140
         		0.4 g, 70% yield
    103 (2,4- dimethoxyphenyl)(methyl)((3-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00141
         		0.5 g, 73% yield
    104 (4-fluorophenyl)(methyl)((3-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00142
         		0.4 g, 69% yield
    105 (2-fluorophenyl)(methyl)((3-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00143
         		0.4 g, 66% yield
    106 (3-methoxyphenyl)(methyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00144
         		0.5 g, 73% yield
    107 (2,5-dichlorophenyl)(methyl)((4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00145
         		0.3 g, 69% yield
    108 (4-methoxyphenyl)(methyl)((6-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)pyridin-3-yl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00146
         		0.4 g, 68% yield
    109 methyl(phenyl)((6-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)pyridin-3-yl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00147
         		0.4 g, 68% yield
    110 methyl(pyridin-2-yl)((6-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)pyridin-3-yl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00148
         		0.2 g, 36% yield
    111 (2,6-difluorobenzyl)(methyl)((6- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)pyridin-3- yl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00149
         		0.2 g, 42% yield
    112 (4-chlorophenyl)(methyl)((3-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00150
         		0.4 g, 64% yield
    113 methyl(pyridin-2-yl)((3-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00151
         		0.3 g, 48% yield
    114 methyl(m-tolyl)((3-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00152
         		0.4 g, 57% yield
    115 methyl(thiazol-2-yl)((3-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00153
         		0.5 g, 71% yield
    116 methyl((4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl)phenyl)imino)(4- (trifluoromethyl)pyridin-2-yl)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00154
         		0.2 g, 64% yield
    117 methyl(4-methylthiazol-2-yl)((4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00155
         		0.3 g, 66% yield
    118 methyl(thiazol-2-yl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00156
         		0.3 g, 63% yield
    119 (4-chlorophenyl)(methyl)((6-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)pyridin-3-yl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00157
         		0.4 g, 56% yield
    120 (2,6-difluorophenyl)(methyl)((6- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)pyridin-3- yl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00158
         		0.4 g, 75% yield
    121 (3,4-difluorophenyl)(methyl)((3- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00159
         		0.6 g, 67% yield
    122 methyl(phenyl)((3-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00160
         		0.5 g, 64% yield
    123 (4-fluorophenyl)(methyl)((6-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)pyridin-3-yl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00161
         		0.5 g, 72% yield
    124 methyl((6-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)pyridin-3- yl)imino)(4- (trifluoromethyl)phenyl)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00162
         		0.3 g, 66% yield
    125 (2-fluorophenyl)(methyl)((6-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)pyridin-3-yl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00163
         		0.5 g, 73% yield
    126 (4-fluorobenzyl)(methyl)((6-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)pyridin-3-yl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00164
         		0.4 g, 63% yield
    127 (3-methoxyphenyl)(methyl)((6-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)pyridin-3-yl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00165
         		0.3 g, 52%
    128 1-((6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)pyridin-3- yl)imino)hexahydro-1λ6-thiopyran 1-oxide
    Figure US20220169621A1-20220602-C00166
         		0.4 g, 56%
    129 4-((6-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)pyridin-3- yl)imino)-1,4λ6-oxathiane 4-oxide
    Figure US20220169621A1-20220602-C00167
         		0.4 g, 61%
    130 methyl(p-tolyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00168
         		0.6 g, 50%
    131 (2,4-difluorophenyl)(methyl)((4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00169
         		0.2 g, 41% yield
    132 methyl((4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl)phenyl)imino)(5- (trifluoromethyl)pyridin-2-yl)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00170
         		0.3 g, 68% yield
    133 4-((4-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)imino)- 1,4λ6-oxathiane 4-oxide
    Figure US20220169621A1-20220602-C00171
         		0.1 g, 35% yield
    134 1-((4-(5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl)phenyl)imino)hexahydro-1λ6- thiopyran 1-oxide
    Figure US20220169621A1-20220602-C00172
         		0.5 g, 78% yield
    135 methyl(4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)phenyl)((4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00173
         		0.5 g, 61% yield
    136 methyl(4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl)phenyl)((3- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)imino)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00174
         		0.1 g, 31% yield
    209 (2-methoxyethyl)(methyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00175
         		0.2 g, 51%
    210 isopropyl(methyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00176
         		0.3 g, 53%
    211 methyl(propyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00177
         		0.2 g, 61%
    212 ethyl(methyl)((4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00178
         		0.2 g, 52%
    213 ((3-fluoro-4-(5-(tifluoromethyl)- 1,2,4-oxadiazol-3- yl)phenyl)imino)(2- fluorophenyl)(methyl)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00179
         		0.3 g, 48%
    214 ((3-fluoro-4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl)phenyl)imino)(methyl)(phenyl)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00180
         		0.4 g, 62%
    215 ((3-fluoro-4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl)phenyl)imino)(methyl)(pyridin- 2-yl)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00181
         		0.1 g, 21%
    216 ((3-methoxy-4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3- yl)phenyl)imino)(methyl)(phenyl)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00182
         		0.2 g 27%
    217 (2-fluorophenyl)((3-methoxy-4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)(methyl)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00183
         		0.3 g, 56%
    218 ((3-methoxy-4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)(4- methoxyphenyl)(methyl)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00184
         		0.3 g, 60%
    219 ((3-methoxy-4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3- yl)phenyl)imino)(methyl)(propyl)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00185
         		0.4 g, 65%
    220 ((3-methoxy-4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3- yl)phenyl)imino)(methyl)(pyridin- 2-yl)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00186
         		0.3 g, 47%
    • Example-3: Preparation of (2-fluorophenyl)(methyl)((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino)-L5-sulfanone (Compound 29)
  • Figure US20220169621A1-20220602-C00187
    • Step 1: 4-((((2-Fluorophenyl)(methyl)(oxo)-I6-sulfanylidene)amino)methyl)benzonitrile
  • Figure US20220169621A1-20220602-C00188
  • To a stirred solution of (2-fluorophenyl)(imino)(methyl)-L6-sulfanone (0.3 g, 1.7 mmol)) in N N-dimethylformamide (8 mL), potassium tert-butoxide (0.4 g, 3.5 mmol) was added at 0° C. under nitrogen atmosphere. The resulting reaction mixture was stirred at 25° C. for 15 minutes and again cooled to 0° C. Then added 4-(bromomethyl)benzonitrile (0.4 g, 2.1 mmol) and reaction mixture was stirred at 25° C. for 30 minutes. Saturated aqueous ammonium chloride solution (10 mL) and ethyl acetate (40 mL) were added to the reaction mixture and stirred at 0° C. for 10 minutes. The ethyl acetate layer was isolated, washed with water (20 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain 4-0((2-fluorophenyl)(methyl)(oxo)-λ6-sulfanylidene)amino)methyl)benzonitrile (0.5 g, 1.7 mmol, 96% yield).
    • Step 2: (Z)-4-((((2-Fluorophenyl)(methyl)(oxo)-/.6-sulfanylidene)amino)methyl)-N′-hydroxybenzimidamide
  • Figure US20220169621A1-20220602-C00189
  • To a stirred solution of 4˜((((2-fluorophenyl)(methyl)(oxo)-/.6-sulfanylidene)amino)methyl)benzonitrile (0.5 g, 1.7 mmol) in ethanol (12 mL), hydroxylamine hydrochloride (0.2 g, 3.0 mmol) and sodium bicarbonate (0.3 g, 3.3 mmol) were added at 25° C. The resulting reaction mixture was heated to 65° C. for 12 h. After completion of the reaction, the reaction mixture was filtered through sintered funnel. The filtrate was evaporated under reduced pressure to obtain 4-((((2-fluorophenyl)(methyl)(oxo)-X6-sulfanylidene)amino)methyl)-N′-hydroxybenzimidamide (0.5 g).
    • Step 3: (2-fluorophenyl)(methyl)(0-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)imino))-2-sulfanone
  • Figure US20220169621A1-20220602-C00190
  • To a stirred solution of 4-((((2-fluorophenyl)(methyl)(oxo)-X6-sulfanylidene)amino)methyl)-N′-hydroxybenzimidamide (0.5 g, 1.6 mmol)) in tetrahydrofuran (10 mL), trifluoroacetic acid (0.2 mL, 1.6 mmol)) was added at 0° C. under nitrogen atmosphere. The resulting reaction mixture was stirred at 25° C. for 16 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (30 mL) and washed three times with water (15 mL). The ethyl acetate layer was washed with aqueous saturated sodium bicarbonate (30 mL) solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude residue was purified by column chromatography (eluent-hexane to 25% ethyl acetate in hexane) on silica gel to obtain (2-fluorophenyl)(methyl)((4-(5-(trifluoromethyl)˜i,2,4-oxadiazol-3-yl)benzyl)imino)˜I6-sulfanone as a gum (0.2 g, 0.5 mmol, 28% yield).
  • TABLE 3
    The following compounds were prepared by the procedure analogous to that of the
    compound no. 29 using appropriate starting materials.
    Compound
    No. IUPAC Name Structure Yield
     22 (4-bromophenyl)(methyl)((4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00191
         		135 mg, 24% yield
     23 (4- methoxyphenyl)(methyl)((4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino- λ6-sulfanone
    Figure US20220169621A1-20220602-C00192
         		365 mg, 58% yield
     24 methyl(4- (trifluoromethoxy)phenyl)((4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00193
         		61 mg, 11% yield
     25 methyl((4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl)benzyl)imino)(4- (trifluoromethyl)phenyl)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00194
         		125 mg 22% yield
     26 methyl(phenyl)((4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00195
         		0.3 g, 36% yield
     27 methyl(pyridin-2-yl)((4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00196
         		0.2 g, 35% yield
     28 (4-chlorophenyl)(methyl)((4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00197
         		0.2 g, 47% yield
    137 methyl(p-tolyl)((4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00198
         		0.1 g, 9% yield
    138 methyl(phenyl)((3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00199
         		0.2 g, 31% yield
    139 (4- methoxyphenyl)(methyl)((3- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino- λ6-sulfanone
    Figure US20220169621A1-20220602-C00200
         		0.4 g, 51% yield
    140 (2,4- dimethoxyphenyl)(methyl)((3- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- sulfanone
    Figure US20220169621A1-20220602-C00201
         		0.3 g, 44% yield
    141 (3,4- difluorophenyl)(methyl)((3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- sulfanone
    Figure US20220169621A1-20220602-C00202
         		0.3, 43% yield
    142 methyl((3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl)benzyl)imino)(4-((4- (trifluoromethyl)pyridin-2- yl)oxy)phenyl)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00203
         		0.4 g, 79% yield
    143 (4-chlorophenyl)(methyl)((3- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00204
         		0.2 g, 56% yield
    144 methyl(thiazol-2-yl)((3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00205
         		0.3 g, 57% yield
    145 (4-fluorophenyl)(methyl)((3- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00206
         		0.3 g, 53% yield
    146 (2-bromo-5- fluorophenyl)(methyl)((3-(5- (trifluoroethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00207
         		0.5 g, 65% yield
    147 (4-bromo-2- fluorophenyl(methyl)((3-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00208
         		0.2 g, 42% yield
    148 (2-fluorophenyl)(methyl)((3- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00209
         		0.2 g, 38% yield
    149 4-((3-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl)benzyl)imino)-1,4λ6- oxathiane 4-oxide
    Figure US20220169621A1-20220602-C00210
         		0.3 g, 67% yield
    150 isopropyl(4- methoxyphenyl)((4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00211
         		0.2 g, 42% yield
    151 isopropyl(phenyl)((4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00212
         		0.2 g, 40% yield
    152 (4- chlorophenyl)(isopropyl)((4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzyl)imino)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00213
         		0.2 g, 38% yield
    • Example 4: —Preparation of N-((2-fluorophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide (Compound No. 155)
  • Figure US20220169621A1-20220602-C00214
    • Step-1:—2-fluorobenzenesulfonamide
  • Figure US20220169621A1-20220602-C00215
  • To a stirred solution of 25% aqueous ammonia (1.1 mL, 12.8 mmol) in tetrahydrofuran (5 mL), 2-fluorobenzenesulfonyl chloride (0.3 g, 1.3 mmol) was added at 0-5° C. The resulting reaction mixture was stirred at 25° C. for 16 h. Sodium bicarbonate (0.16 g, 1 9 mmol) was added and stirred at 25° C. for 10 minutes. The reaction mixture was concentrated to obtain 2-fluorobenzenesulfonamide (0.2 g, 1.3 mmol, 98% yield).
    • Step-2: —N-((2-fluorophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide (Compound No. 155)
  • Figure US20220169621A1-20220602-C00216
  • To a stirred solution of 4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid (0.3 g, 1.0 mmol) in dry N, N-di methyl formamide (5 mL) under nitrogen atmosphere, 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.4 g, 2.0 mmol) was added followed by the addition of 4-dimethylaminopyridine (0.2 g, 2.0 mmol) and 2-fluorobenzenesulfonamide (0.2 g, 1.0 mmol) at 25° C. The resulting reaction mixture was stirred for 12 h at 25° C. After completion of the reaction, the reaction mixture was diluted with dichloromethane (30 mL) and washed thrice with water (20 mL). Dichloromethane layer was dried over anhydrous sodium sulphate. The volatiles were evaporated under vacuum. Crude residue was purified by preparative HPLC to obtain N-((2-fluorophenyl)sulfonyl)-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide (0.2 g, 35% yield).
  • TABLE 4
    The following compounds were prepared the procedure analogous to that of the
    Compound 155 using appropriate starting materials.
    Compound
    No. IUPAC Name Structure Yield
    153 N-tosyl-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00217
         		0.1 g, 24% yield
    154 N-((5-chloro-2- methoxyphenyl)sulfonyl)-4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00218
         		0.2 g, 44% yield
    156 N-((2,4- dichlorophenyl)sulfonyl)-4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00219
         		0.3 g, 57% yield
    157 N-((4- methoxyphenyl)sulfonyl)-4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00220
         		0.1 g, 16% yield
    158 N-((3- methoxyphenyl)sulfonyl)-4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00221
         		0.1 g, 26% yield
    159 4-(5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)-N-((4- (trifluoromethyl)phenyl) sulfonyl)benzamide
    Figure US20220169621A1-20220602-C00222
         		0.3 g, 56% yield
    160 N-(pyridin-3-ylsulfonyl)-4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00223
         		0.2 g, 29% yield
    161 N-((2,5- difluorophenyl)sulfonyl)-4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00224
         		0.2 g, 41% yield
    162 N-((4- bromophenyl)sulfonyl)-4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00225
         		0.2 g, 43% yield
    163 N-((2,6- dichlorophenyl)sulfonyl)-4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00226
         		0.2 g, 47% yield
    164 N-((3- fluorophenyl)sulfonyl)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00227
         		0.3 g, 52% yield
    • Example 5: —Preparation of ((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(2-fluorophenyl)(methyl){circumflex over ( )}5-sulfanone (Compound No. 165)
  • Figure US20220169621A1-20220602-C00228
    • Step 1: —3-Fluoro-4-(((2-fluorophenyl)(methyl)(oxo)-X6-sulfaneylidene)amino)benzonitrile
  • Figure US20220169621A1-20220602-C00229
  • To a stirred solution of (2-fluorophenyl)(imino)(methyl)-L6-sulfanone (0.4 g, 2.3 mmol) in N N-dimethylformamide (8 mL), potassium tert-butoxide (0.3 g, 2.8 mmol) was added at 0° C. and allowed to stir at 2.5° C. tor 10 minutes. The reaction mixture was cooled again to 0° C. and 3,4-difluorobenzonitrile (0.3 g, 2.3 mmol) was added. The stirring was continued at 25° C. for 4 h. The reaction mixture was diluted with ethyl acetate (60 mL) and washed twice with water (20 mL). The obtained crude product was purified by flash column chromatography on silica gel using hexane to 50% ethyl acetate in hexane as an eluent to obtain pure 3-fluoro-4-(((2-fluorophenyl)(methyl)(oxo)-) λ6-sulfanylidene)amino)benzonitrile (0.5 g, 1 6 mmol, 71% yield).
    • Step 2: —3-Iduoro-4-(((2-fluorophenyl)(methyl)(oxo)-/.6-sulfanylidene)amino)-N′-hydroxybenzimidamide
  • Figure US20220169621A1-20220602-C00230
  • To a stirred solution of 3-fluoro-4-(((2-fluorophenyl)(methyl)(oxo)-λ6-sulfanylidene)amino)benzonitrile (0.5 g, 1.6 mmol) in ethanol (8 mL), sodium bicarbonate (0.3 g, 3.3 mmol) and hydroxylamine hydrochloride (0.2 g, 3.3 mmol) were added at 25° C. The resulting reaction mixture was stirred at 70° C. for 16 h. The reaction mixture was filtered and the filtrate was evaporated under vacuum to obtain 3-fluoro-4-(((2-fluorophenyl)(methyl)(oxo)-λ6-sulfanylidene)amino)-N′-hydroxybenzimidamide (0.5 g, 1.5 mmol, 90% yield)
    • ((2-Fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(2-fluorophenyl)(methyl)-λ6-sulfanone
  • Figure US20220169621A1-20220602-C00231
  • To a stirred solution of 3-fluoro-4-(((2-fluorophenyl)(methyl)(oxo)-′/.6-sulfanylidene)amino-N′-hydroxybenzimidamide (0.5 g, 1.5 mmol) in tetrahydrofuran (8 mL), trifluoro acetic anhydride (0.3 mL, 2.2 mmol) was added slowly at 0° C. under nitrogen atmosphere and then stirred at 25° C. for 16 h. The resulting reaction mixture was diluted with ethyl acetate (50 mL). The ethyl acetate layer was washed twice with aqueous sodium bicarbonate solution (20 mL), dried over anhydrous sodium sulphate and evaporated under vacuum. Crude product was purified by flash column chromatography on silica gel using hexane to 50% ethyl acetate in hexane as an eluent to obtain ((2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)imino)(2-fluorophenyl)(methyl)-λ6-sulfanone (0.5 g, 1.2 mmol, 84% yield).
  • TABLE 5
    The following compounds were prepared by the procedure analogous to that of the
    Compound 165 using appropriate starting materials.
    Compound
    No. IUPAC Name Structure Yield
    166 ((2-fluoro-4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl)phenyl)imino)(2- fluorophenyl)(methyl)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00232
         		0.5 g, 84% yield
    166 ((2-fluoro-4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl)phenyl)imino)(methyl)(phenyl)- λ6-sulfanone
    Figure US20220169621A1-20220602-C00233
         		0.4 g, 60% yield
    167 (4-chlorophenyl)((2-fluoro-4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)imino)(methyl)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00234
         		0.4 g, 70% yield
    168 ((2-fluoro-4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl)phenyl)imino)(methyl)(pyridin- 2-yl)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00235
         		0.2 g, 40% yield
    169 ((2-fluoro-4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl)phenyl)imino)(3- fluorophenyl)(methyl)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00236
         		0.4 g, 63% yield
    170 ((2-fluoro-4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl)phenyl)imino)(4- fluorophenyl)(methyl)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00237
         		0.4 g, 53% yield
    171 ((2-fluoro-4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl)phenyl)imino)(4- methoxyphenyl)(methyl)-λ6- sulfanone
    Figure US20220169621A1-20220602-C00238
         		0.3 g, 44% yield
    • Example 6: —Preparation of 2-fluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-/.6-sulfaneylidene)benzamide (compound no. 172)
  • Figure US20220169621A1-20220602-C00239
    • Step 1: —N′-hydroxy-4-(methylthio)benzimidamide
  • Figure US20220169621A1-20220602-C00240
  • N′-hydroxy-4-(methylthio)benzimidamide (10.1 g) was prepared by the procedure described in step 2 of example 1.
    • Step 2: —3-(4-(methylthio)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole
  • Figure US20220169621A1-20220602-C00241
  • 3-(4-(Methylthio)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole (12.3 g, 83% yield) was prepared by the procedure described in step-3 of example 1.
    • Step 3:—Synthesis of imino(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfanone
  • Figure US20220169621A1-20220602-C00242
  • Imino(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-X6-sulfanone (10.5 g, 94% yield) was prepared by the procedure described in step-6 of example 1.
    • Step 4:—Synthesis of 2-fluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yllphenyll-X{circumflex over ( )}-sulfaneylidenelbenzamide
  • Figure US20220169621A1-20220602-C00243
  • To a stirred solution of imino(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-1G-sulfanone (0.3 g, 1.0 mmol), 4-Dimethylaminopyridine (0.01 g, 0.1 mmol) and triethylamine (0.2 ml, 1.5 mmol) in dichloromethane (10 mL), 2-fluorobenzoyl chloride (0.163 g, 1.030 mmol) was added at 0° C. The resulting reaction mixture was stirred for 2 h at 25° C. The volatiles were evaporated and the residue was extracted by ethyl acetate (60 mL). Ethyl acetate layer was washed thrice with water (10 mL), dried over anhydrous sodium sulphate and concentrated under vacuum. Cmde product was purified by flash column chromatography on silica gel using hexane to 60% ethyl acetate in hexane as an eluent to obtain pure 2-fluoro-N-(methyl(oxo)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-λ6-sulfanylidene)benzamide (0.3 g, 0.8 mmol, 79% yield).
  • TABLE 6
    The following compounds were prepared by the procedure analogous to that of the
    compound 172 using appropriate starting materials.
    Compound
    No. IUPAC Name Structure Yield
    172 2-fluoro-N-(methyl(oxo)(4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)-λ6- sulfaneylidene)benzamide
    Figure US20220169621A1-20220602-C00244
         		0.3 g, 79% yield
    173 3-methoxy-N-(methyl(oxo)(4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)-λ6- sulfaneylidene)benzamide
    Figure US20220169621A1-20220602-C00245
         		0.3 g, 79% yield
    174 3-fluoro-N-(methyl(oxo)(4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)-λ6- sulfaneylidene)benzamide
    Figure US20220169621A1-20220602-C00246
         		0.2 g, 43% yield
    175 4-chloro-2-fluoro-N- (methyl(oxo)(4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)-λ6- sulfaneylidene)benzamide
    Figure US20220169621A1-20220602-C00247
         		0.3 g, 57% yield
    176 2-chloro-6-fluoro-N- (methyl(oxo)(4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)-λ6- sulfaneylidene)benzamide
    Figure US20220169621A1-20220602-C00248
         		0.2 g, 36% yield
    177 N-(methyl(oxo)(4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)-λ6- sulfaneylidene)benzamide
    Figure US20220169621A1-20220602-C00249
         		0.2 g, 41% yield
    178 N-(methyl(oxo)(4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)-λ6-sulfaneylidene)-2- phenylacetamide
    Figure US20220169621A1-20220602-C00250
         		0.1 g, 30% yield
    179 4-chloro-N-(methyl(oxo)(4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)-λ6- sulfaneylidene)benzamide
    Figure US20220169621A1-20220602-C00251
         		0.3 g, 64% yield
    180 N-(methyl(oxo)(4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)-λ6- sulfaneylidene)pivalamide
    Figure US20220169621A1-20220602-C00252
         		0.3 g, 78% yield
    181 N-(methyl(oxo)(4-(5- (trifluoromethyl)-1,2,4-oxadiazol- 3-yl)phenyl)-λ6- sulfaneylidene) cyclopropanecarboxamide
    Figure US20220169621A1-20220602-C00253
         		0.3 g, 77% yield
    • Example 7: —Preparation of ((3-chlorobenzyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-λ6-sulfanone (Compound No. 182)
  • Figure US20220169621A1-20220602-C00254
    • Step 1: —4-(S-methylsulfonimidoyl)benzonitrile
  • Figure US20220169621A1-20220602-C00255
  • 4-(S-methylsulfonimidoyl)benzonitrile (6 g, 83% yield) was prepared by the procedure described in step-6 of example 1.
    • Step 2: —4-(N-(3-chlorobenzyl)-S-methylsulfonimidoyl)benzonitrile
  • Figure US20220169621A1-20220602-C00256
  • 4-(S-methylsulfonimidoyl)benzonitrile (0.5 g, 2.8 mmol) was dissolved in N,N-di methyl formamide (5 mL), followed by addition of potassium-f-butoxide (0.4 g, 3 3 mmol) at 0° C. and stirred for 15 minutes at 0° C. 3-Chlorobenzyl bromide (0.5 mL, 4.2 mmol) was added and allowed to stir for 3 h. After completion of the reaction, ethyl acetate (25 mL) and saturated ammonium chloride solution (10 mL) were added to the reaction mixture. Ethyl acetate layer was isolated and washed twice with water (10 mL), dried over anhydrous sodium sulphate and concentrated under vacuum to obtain 4-(N-(3-chlorobenzyl)-S-methylsulfonimidoyl)benzonitrile (0.8 g).
    • Step 3: —4-(N-(3-chlorobenzyl)-S-methylsulfonimidoyl)-N′-hydroxybenzimidamide
  • Figure US20220169621A1-20220602-C00257
  • 4-(N-(3-chlorobenzyl)-S-methylsulfonimidoyl)-N′-hydroxybenzimidamide (1.2 g) was prepared by procedure as described in step-2 of example 1.
    • Step 4: —((3-chlorobenzyl)imino)(methyl)(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)-L6-sulfanone
  • Figure US20220169621A1-20220602-C00258
  • To a stirred solution of 4-(N-(3-chlorobenzyl)-S-methyisulfonimidoyl)-N′-hydroxybenzimidamide (1.2 g, 3.8 mmol) in tetrahydrofuran (6 mL), trifluoroacetic anhydride (0.6 mL, 4.5 mmol) was added slowly at 5° C. under nitrogen atmosphere. The resulting reaction mixture was stirred for 18 h at 25° C. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (60 mL). The ethyl acetate layer was washed with saturated sodium bicarbonate solution (30 mL), dried over anhydrous sodium sulphate and concentrated under vacuum. The crude product was purified by column chromatography on silica gel using hexane to 50% ethyl acetate in hexane as an eluent to obtain ((3-chlorobenzyl)imino)(methyl)(4-(5-(trifluoromethyl)-L2,4-oxadiazol-3-yl)phenyl)-},6-sulfanone (0.6 g, 1.2 mmol, 38% yield)
  • TABLE 7
    The following compounds were prepared by the procedure analogous to that of the
    compound 182 using appropriate stating materials.
    Compound
    No. IUPAC Name Structure Yield
    183 ((4-fluorobenzyl)imino)(methyl)(4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00259
         		0.3 g, 26% yield
    184 ((2,4- difluorobenzyl)imino)(methyl)(4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00260
         		0.3 g, 30% yield
    185 ((3-fluorobenzyl)imino)(methyl)(4- (5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl)phenyl)-λ6-sulfanone
    Figure US20220169621A1-20220602-C00261
         		0.3 g, 19% yield
    • Example 8: Preparation of 3N-((4-fluorophenyl)(methyl)(oxo)-X6-sulfaneylidene)-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide (Compound No. 186)
  • Figure US20220169621A1-20220602-C00262
    • Step-1: —2-(4-(N′-hydroxycarbamimidoyl)phenyl)acetic acid
  • Figure US20220169621A1-20220602-C00263
  • To a stirred solution of 2-(4-cyanophenyl (acetic acid (5.0 g, 31.0 mmol) in ethanol (120 mL), 50% of aqueous hydroxylamine solution (4.8 mL, 155 mmol) was added at 0° C. and stirred at 65° C. for 4 h. The reaction mixture was concentrated under vacuum to obtain 2-(4-(N′-hydroxycarbamimidoyl)phenyl)acetic acid (5.5 g).
    • Step-2: —Preparation of 2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid
  • Figure US20220169621A1-20220602-C00264
  • To a stirred solution of 2-(4-(N′-hydroxycarbamimidoyl)phenyl)acetic acid (5.5 g, 28.3 mmol) in tetrahydrofuran (100 mL), trifluoroacetic anhydride (8 mL, 56 6 mmol) was added at 0° C. under nitrogen atmosphere and stirred at 25° C. for 16 h. After completion of the reaction, the reaction mixture was concentrated and purified by column chromatography on silica gel using hexane to 60% ethyl acetate in hexane as an eluent to obtain pure 2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid (6.0 g, 78% yield).
    • Step-3: —Preparation of N-((4-fluorophenyl)(methyl)(oxo)-/.6-sulfaneylidene)-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide
  • Figure US20220169621A1-20220602-C00265
  • To a stirred solution of 2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid (0.4 g, 1.3 mmol) in dichloromethane (10 mL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.5 g, 2.6 mmol) and 4-dimethylaminopyridine (0.5 g, 3 9 mmol) were added at 0-5° C. under nitrogen atmosphere. (4-fluorophenyl)(imino)(methyl)-λ6-sulfanone (0.3 g, 1.4 mmol was added and stirred at 25° C. for 16 h. The resulting reaction mixture was diluted with dichloromethane (60 mL) and washed twice with water (20 mL). Dichloromethane layer was collected and dried over anhydrous sodium sulphate and concentrated under vacuum. Crude product was purified by preparative HPLC to obtain N-((4-fluorophenyl)(methyl)(oxo)-λ6-sulfanylidene)-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)acetamide (0.3 g, 0.7 mmol, 54% yield).
  • TABLE 8
    The following compounds were prepared by the procedure analogous to that of the
    compound 186 using appropriate starting materials.
    Compound
    No. IUPAC Name Structure Yield
    187 N-((4- methoxyphenyl)(methyl)(oxo)- λ6-sulfaneylidene)-2-(4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl)phenyl)acetamide
    Figure US20220169621A1-20220602-C00266
         		0.3 g, 54% yield
    188 N-((2- fluorophenyl)(methyl)(oxo)- λ6-sulfaneylidene)-2-(4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl)phenyl)acetamide
    Figure US20220169621A1-20220602-C00267
         		0.2 g, 42% yield
    189 N-((4- chlorophenyl)(methyl)(oxo)- λ6-sulfaneylidene)-2-(4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl)phenyl)acetamide
    Figure US20220169621A1-20220602-C00268
         		0.2 g, 49% yield
    190 N-((3- fluorophenyl)(methyl)(oxo)- λ6-sulfaneylidene)-2-(4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl)phenyl)acetamide
    Figure US20220169621A1-20220602-C00269
         		0.2 g, 41% yield
    191 N-(methyl(oxo)(thiazol-2-yl)- λ6-sulfaneylidene)-2-(4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl)phenyl)acetamide
    Figure US20220169621A1-20220602-C00270
         		0.1 g, 23% yield
    192 N-((3- methoxyphenyl)(methyl)(oxo)- λ6-sulfaneylidene)-2-(4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl)phenyl)acetamide
    Figure US20220169621A1-20220602-C00271
         		0.3 g, 57% yield
    193 N-((2,4- difluorobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-2-(4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl)phenyl)acetainide
    Figure US20220169621A1-20220602-C00272
         		0.2 g, 44% yield
    194 N-(methyl(oxo)(phenyl)-λ6- sulfaneylidene)-2-(4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl)phenyl)acetamide
    Figure US20220169621A1-20220602-C00273
         		0.2 g, 36% yield
    195 N-((2- fluorobenzyl)(methyl)(oxo)- λ6-sulfaneylidene)-2-(4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl)phenyl)acetamide
    Figure US20220169621A1-20220602-C00274
         		0.2 g, 42% yield
    • Example 9: —Preparation of N42-fluorophenyl)(methyl)(oxo)-46-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)picolinamide
  • Figure US20220169621A1-20220602-C00275
    • Step 1: —Synthesis of 5-(N′-hydroxycarbamimidoyl)picolinic acid
  • Figure US20220169621A1-20220602-C00276
  • To a stirred solution of 5-cyanopicolinic acid (0.5 g, 3.4 mmol) in ethanol (TO mL). 50% of aqueous hydroxylamine solution (0.52 mL, 16.9 mmol) was added. The resulting reaction mixture was stirred at 65° C. for 4 hours. After completion of the reaction, the volatiles were evaporated under vacuum to obtain 5-(N′-hydroxycarbamimidoyl)picolinic acid (0.6 g).
    • Step 2: —5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)picolinic acid
  • Figure US20220169621A1-20220602-C00277
  • To a stirred solution of 5-(N′-hydroxycarbamimidoyl)picolinic acid (6 g, 33 mmol) in tetrahydrofuran (50 mL), trifluoroacetic anhydride (8.4 mL, 59.6 mmol) was added slowly at 0-5° C. under nitrogen atmosphere. The resulting reaction mixture was stirred for 18 h at 25° C. Solvent was removed under reduced pressure. Crude residue was stirred with water (20 mL) at 25° C. Obtained precipitate was filtered and solid was dried under vacuum to obtain 5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)picolinic acid (7.5 g, 28.9 mmol).
    • Step 3: —Synthesis of N-((2-fluorophenyl)(methyl)(oxo)-L5-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)picolin amide
  • Figure US20220169621A1-20220602-C00278
  • N-((2-fluorophenyl)(methyl)(oxo)-X6-sulfaneylidene)-5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)picolinamide (0.13 g, 23% yield) was synthesized by the procedure as described in step-3 of example 8.
  • TABLE 9
    The following compounds were prepared by the procedure analogous to that of tire
    Compound 196 using appropriate starting materials.
    Compound
    No. IUPAC Name Structure Yield
    197 N-(methyl(oxo)(phenyl)-λ6- sulfaneylidene-5-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)picolinamide
    Figure US20220169621A1-20220602-C00279
         		0.3 g, 49% yield
    198 N-((4- methoxyphenyl)(methyl)(oxo)- λ6-sulfaneylidene)-5-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)picolinamide
    Figure US20220169621A1-20220602-C00280
         		0.3 g, 52% yield
    199 N-(methyl(oxo)(pyridin-2-yl)- λ6-sulfaneylidene)-5-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)picolinamide
    Figure US20220169621A1-20220602-C00281
         		0.2 g, 38% yield
    200 N-((2- methoxyethyl)(methyl)(oxo)-λ6- sulfaneylidene)-5-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)picolinamide
    Figure US20220169621A1-20220602-C00282
         		0.3 g, 65% yield
    201 2-fluoro-N- (methyl(oxo)(phenyl)-λ6- sulfanylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00283
         		0.2 g, 42% yield
    202 2-fluoro-N-((4- methoxyphenyl)(methyl)(oxo)- λ6-sulfanylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00284
         		0.2 g, 51% yield
    203 2-fluoro-N-((2- fluorophenyl)(methyl)(oxo)-λ6- sulfanylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00285
         		0.1 g, 18% yield
    204 N-(ethyl(methyl)(oxo)-λ6- sulfanylidene)-2-fluoro-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00286
         		0.05 g, 16% yield
    205 2-fluoro-N- (methyl(oxo)(pyridin-2-yl)-λ6- sulfanylidene)-4-(5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl)benzamide
    Figure US20220169621A1-20220602-C00287
         		0.1 g, 25% yield
    • Example 10—Preparation of N-(methyl(oxo)(phenyl)-//′-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide (compound no. 222)
  • Figure US20220169621A1-20220602-C00288
    • Step 1: —Preparation of methyl-4-(2-amino-2-(hydroxyimino)ethyl)benzoate
  • Figure US20220169621A1-20220602-C00289
  • To a solution of methyl 4-(cyanomethyl)benzoate (9.5 g, 54.2 mmol) in ethanol (100 mL), hydroxylamine hydrochloride (6.78 g, 98 mmol) and sodium bicarbonate (8.20 g, 98 mmol) were added. The resulting reaction mixture was stirred at 65° C. for 18 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to obtain methyl-4-(2-amino-2-(hydroxyimino)ethyl)benzoate (1L2 g, 53.8 mmol, 99% yield).
    • Step 2: —Preparation of methyl 4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzoate
  • Figure US20220169621A1-20220602-C00290
  • To a solution of methyl-4-(2-amino-2-(hydroxyimino)ethyl)benzoate (11.2 g, 53.8 mmol) in tetrahydrofuran (100 mL), trifluoroacetic anhydride (11.4 mL, 81 mmol) was added at 0-5° C. and stirred at 25° C. for 16 h. The resulting reaction mixture was poured into ice cold mixture of ethyl acetate (300 mL) and saturated sodium bicarbonate solution (200 mL) with stirring (caution—pH must remain basic). The ethyl acetate layer was separated, washed twice with saturated sodium bicarbonate solution (50 mL), dried over anhydrous sodium sulphate and concentrated. The crude product was purified by flash column chromatography on silica gel using 0-50% ethyl acetate in hexane as an eluent to obtain pure methyl 4((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzoate (15.4 g, 31.4 mmol, 58% yield).
    • Step-3: —N-(methyl(oxo)(phenyl)-X6-sulfaneylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide (compound no. 222)
  • Figure US20220169621A1-20220602-C00291
  • To a stirred solution of methyl 4((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzoate (0.4 g, 1.2 mmol), imino(methyl)(phenyl)-V-sulfanone (0.5 g, 3.1 mmol) and toluene (7 mL), trimethylaluminium 25% in hexane (1.529 ml, 3.06 mmol) was added at 0-5° C. and stirred at 65° C. for 16 h. The resulting reaction mixture was cooled to 25° C. and poured into a mixture of 5% aq. acetic acid (7 mL) and ethyl acetate (15 mL), stirred at 25° C. for 10 minutes, organic layer was isolated. Aqueous layer was again extracted into ethyl acetate (20 mL). Ethyl acetate layer was washed by water (20 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification was done by column chromatography on silica gel using hexane to 60% ethyl acetate in hexane as an eluent to obtain N-(methyl(oxo)(phenyl)4,6-sulfanylidene)-4-((5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)methyl)benzamide (0.4 g, 1.0 mmol, 78% yield).
  • TABLE 10
    The following compound was prepared by the procedure analogous to that of the
    compound no. 222 using appropriate starting materials.
    Compound
    No. IUPAC Name Structure Yield
    221 N-(methyl(oxo)(propyl)-λ6- sulfaneylidene)-4-((5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl)methyl)benzamide
    Figure US20220169621A1-20220602-C00292
         		0.2 g, 40% yield
    • BIOLOGY EXAMPLES Biological Test Examples for Fungal Pathogens Example 1: Pyricularia oryme (Rice Blast)
  • Compounds were dissolved in 0.3% DMSO & then added to Potato Dextrose Agar medium just prior to dispensing it into petri dishes. 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile petri-plates. After solidification, each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 25° C. temperature and 60% relative humidity for seven days and radial growth was measured. Compounds 3 13 14 15 17 18 19 20 22 23 27 29 96 97 106 114 117 122 124 127 130 133 134 137 138 139 141 143 144 145 146 147 148 149 151 151 152 152 165 166 167 169 171 181 182 183 184 & 185 at 300 ppm gave more than 70% control in these tests when compared to the untreated check which showed extensive disease development.
    • Example 2: Rhizoctonia solani (Rice Sheath Blight/Potato Black Scurf)
  • Compounds were dissolved in 0.3% DMSO & then added to Potato Dextrose Agar medium just prior to dispensing it into petri dishes. 5 mL, medium with compound in the desired concentration was dispensed into 60 mm sterile petri-plates. After solidification, each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 25° C. temperature and 60% relative humidity for seven days and radial growth was measured. Compounds 15 50 90 128 & 133 at 300 ppm gave more than 70% control in these tests when compared to the untreated check which showed extensive disease development.
    • Example 3: Botrytis cinerea (Gray Mold)
  • Compounds were dissolved in 0.3% DMSO & then added to Potato Dextrose Agar medium just prior to dispensing it into petri dishes. 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile petri-plates. After solidification, each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 22° C. temperature and 90% relative humidity for seven days and radial growth was measured. Compounds 14 15 17 23 48 90 108 109 133 138 139 140 153 156 & 157 at 300 ppm gave more than 70% in these tests when compared to the untreated check which showed extensive disease development.
    • Example 4: Alternaria solani (Early Blight of Tomato/Potato)
  • Compounds were dissolved in 0.3% DMSO & then added to Potato Dextrose Agar medium just prior to dispensing it into petri dishes. 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile petri-plates. After solidification each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 25° C. temperature and 60% relative humidity for seven days and radial growth was measured. Compounds 13 14 15 17 18 20 23 33 47 48 56 59 62 71 73 75 94 96 99 108 109 117 137 148 157 158 162 & 163 at 300 ppm gave more than 70% control in these tests when compared to the untreated check which showed extensive disease development.
    • Example 5: Colletotrichum capsici (Anthracnose)
  • Compounds were dissolved in 0.3% DMSO & then added to Potato Dextrose Agar medium just prior to dispensing it into petri dishes. 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile petri-plates. After solidification, each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 25° C. temperature and 60% relative humidity for seven days and radial growth was measured. Compounds 13 15 17 18 22 23 133 156 181 at 300 ppm gave more than 70% control in these tests when compared to the untreated check which showed extensive disease development.
    • Example 6: Septoria lycopersici (Leaf Spot of Tomato)
  • Compounds were dissolved in 0.3% DMSO & then added to Potato Dextrose Agar medium just prior to dispensing it into petri dishes. 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile petri-plates. After solidification, each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 25° C. temperature and 70% relative humidity for seven days and radial growth was measured. Compound 134 at 300 ppm gave more than 70% control in these tests when compared to the untreated check which showed extensive disease development.
    • Example 7: Fusarium culmorum (Foot Rot of Cereals)
  • Compounds were dissolved in 0.3% DMSO & then added to Potato Dextrose Agar medium just prior to dispensing it into petri dishes. 5 mL medium with compound in the desired concentration was dispensed into 60 mm sterile petri-plates. After solidification, each plate was seeded with 5 mm size mycelial disc taken form periphery of actively growing virulent culture plate. Plates were incubated in growth chambers at 25° C. temperature and 60% relative humidity for seven days and radial growth was measured.
    • Example 8: Phakopsora pachyrhizi Test in Soybean
  • Compounds were dissolved in 2% DMSO/Acetone & then mixed with water to the calibrated spray volume of 50 mL and poured into the spray bottles for further applications.
  • To test the preventive activity of compounds, healthy young soybean plants raised in the greenhouse were sprayed with active compound preparation at the stated application rates inside the spray cabinets using hallowcone nozzles. One day after treatment, the plants were inoculated with spore suspension containing 2.1×106 Phakopsora pachyrhizi inoculum. The inoculated plants were then kept in greenhouse chamber at 25° C. temperature & 90% relative humidity for disease expression.
  • A visual assessment of compound's performance was carried out by rating the disease severity (0-100% scale) on treated plants on 3, 7, 10 & 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated control. The sprayed plants were also assessed for compound's plant compatibility by recording symptoms like necrosis, chlorosis & stunting.
  • Compounds 1 2 3 4 5 6 7 9 10 12 14 15 17 18 19 20 21 22 23 25 26 27 28 31 36 38 40 42 47 48 50 51 52 53 56 57 58 59 62 71 75 85 89 91 92 99 108 109 110 showed >90% at 500 ppm control in these tests when compared to the untreated check which showed extensive disease development.

Claims (21)

1-13. (canceled)
14. A compound of Formula Ia;
Figure US20220169621A1-20220602-C00293
wherein L1 is a direct bond;
A is phenyl;
L2 is a fragment selected from the group of
Figure US20220169621A1-20220602-C00294
wherein, k is an integer ranging from 0 to 4; an expression “#” indicates the point of attachment;
R7 and R8 are independently selected from hydrogen, halogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; or
R7 and R8 together with the atoms to which they are attached may form 3- to 5-membered non-aromatic carbocylic ring or heterocyclic ring which may be optionally substituted with halogen, C1-C2-alkyl, C1-C2-haloalkyl or C1-C2-alkoxy;
R9 is selected from the group consisting of hydrogen; NRgRh, wherein, Rg and Rh independently represent hydrogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C3-C8-cycloalkyl; (C═O)—Ri, wherein, Ri represents hydrogen, halogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy; C1-8-alkyl-S(O)0-2Rj, wherein Rj represents hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl; C1-C6-alkyl-(C═O)—Ri, CRi═NRg, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C4-C8-cycloalkenyl, C5-C8-cycloalkynyl, C7-C19-aralkyl:
wherein, Rg may optionally be substituted with one or more identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkoxycarbonyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl and di-C1-C6-alkylaminocarbonyl;
R10 is selected from the group consisting of halogen, hydroxy, cyano, —OR12, —NR13R14, nitro, —SH, —SCN, —COR15, —C(═O)OR12, —C(═O)NR13R14, —NR13C(═O)R15, —O(C═O)R15, —O(C═O)NR13R14, —C(═NOR13)R15, —NR13SO2R16, —CSR16, —C(═S)OR12, —C(═S)NR13R14, —NR13C(═S)R15, —O(C═S)R15, —O(C═S)NR13R14, —O(C═S)SR16, —N═C(R15)2, —NHCN, —SO2NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO2NR12R13, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkyl-C3-C8-cycloalkyl, C3-C8-halocycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkyl-C1-C6-thioalkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-haloalkylamino-C1-C6-alkyl, C3-C8-cycloalkylamino, C3-C8-cycloalkylamino-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, C3-C8-halocycloalkoxy, C3-C8-cycloalkyl-C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkylcarbonylalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfinyl, tri-C1-C6-alkylsilyl, C1-C6-alkylsulfonylamino, C1-C6-haloalkylsulfonylamino, C1-C6-alkylcarbonylthio, C1-C6-alkylsulfonyloxy, C1-C6-alkylsulfinyloxy, C6-C10-arylsulfonyloxy, C6-C10-arylsulfinyloxy, C6-C10-arylsulfonyl, C6-C10-arylsulfinyl, C6-C10-arylthio, C1-C6-cyanoalkyl, C2-C6-alkenylcarbonyloxy, C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-alkylthio-C1-C6-alkoxy, C2-C6-haloalkenylcarbonyloxy, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxy-C2-C6-alkynyl, C2-C6-alkynylthio, C3-C8-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C8-cycloalkyl-C1-C6-alkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl-C1-C6-alkylamino, C1-C6-haloalkylcarbonyl-C1-C6-alkylamino, C1-C6-alkoxycarbonyl-C1-C6-alkylamino, C2-C6-alkenylthio, C1-C6-alkoxy-C1-C6-alkylcarbonyl, C1-C6-haloalkoxycarbonylamino, di(C1-C6-haloalkylamino-C1-C6-alkyl, C3-C8-halocycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy(C1-C6-alkyl)aminocarbonyl, C1-C6-haloalkylsulfonylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, C1-C6-alkoxycarbonylalkoxy, C1-C6-alkylaminothiocarbonylamino, C3-C8-cycloalkyl-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-alkylthiocarbonyl, C3-C8-cycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxycarbonyl, di-C1-C6-alkylaminothiocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-haloalkoxy, C3-C8-halocycloalkoxy-C1-C6-alkyl, di-C1-C6-alkylaminocarbonylamino, C1-C6-alkoxy-C2-C6-alkenyl, C1-C6-alkylthiocarbonyloxy, C1-C6-haloalkoxy-C1-C6-alkoxy, C1-C6-haloalkylsulfonyloxy, C1-C6-alkoxy-C1-C6-haloalkyl, di(C1-C6-haloalkyl)amino, di-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylaminocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkylamino, tri-C1-C6-alkylsilyl-C2-C6-alkynyloxy, tri-C1-C6-alkylsilyloxy, tri-C1-C6-alkylsilyl-C2-C6-alkynyl, cyano(C1-C6-alkoxy)-C1-C6-alkyl, di-C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkoxysulfonyl, C3-C8-halocycloalkoxycarbonyl, C1-C6-alkyl-C3-C8-cycloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6-alkynyloxycarbonyl, C1-C6-cyanoalkoxycarbonyl, C1-C6-alkylthio-C1-C6-alkoxycarbonyl, C2-C6-alkynylcarbonyloxy, C2-C6-haloalkynylcarbonyloxy, cyanocarbonyloxy, C1-C6-cyanoalkylcarbonyloxy, C3-C8-cycloalkylsulphonyloxy, C3-C8-cycloalkyl-C1-C6-alkylsulphonyloxy, C3-C8-halocycloalkylsulphonyloxy, C2-C6-alkenylsulphonyloxy, C2-C6-alkynylsulphonyloxy, C1-C6-cyanoalkylsulphonyloxy, C2-C6-haloalkenylsulphonyloxy, C2-C6-haloalkynylsulphonyloxy, C2-C6-alkynylcycloalkyloxy, C2-C6-cyanoalkenyloxy, C2-C6-cyanoalkynyloxy, C1-C6-alkoxycarbonyloxy, C2-C6-alkenyloxycarbonyloxy, C2-C6-alkynyloxycarbonyloxy, C1-C6-alkoxy-C1-C6-alkylcarbonyloxy, sulfilimines, sulfoximines, SF5 and Z1Q1;
Z1 and Z2 are independently a direct bond, CR2dR3d, N, O, C(O), C(S), C(═CR2dR3d) or S(O)0-2;
Q1 and Q2 are independently selected from phenyl, benzyl, naphthalenyl, a 5- or 6-membered aromatic ring, an 8- to 11-membered aromatic multi-cyclic ring system, an 8- to 11-membered aromatic fused ring system, a 5- or 6-membered heteroaromatic ring, an 8- to 11-membered heteroaromatic multi-cyclic ring system or an 8- to 11-membered heteroaromatic fused ring system; wherein the heteroatom of the heteroaromatic rings is selected from N, O or S, and each ring or ring system may be optionally substituted with one or more substituents independently selected from R17; or
Q1 and Q2 are independently selected from a 3- to 7-membered non-aromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered non-aromatic heterocyclic ring, an 8- to 15-membered non-aromatic multi-cyclic ring system, an 5- to 15 membered spirocyclic ring system, or an 8- to 15-membered non-aromatic fused ring system, wherein, the heteroatom of the non-aromatic rings is selected from N, O or S(O)0-2, and C ring member of the non-aromatic carbocylic or non-aromatic heterocyclic rings or ring systems may be replaced with C(O), C(S), C(═CR2cR3c) or C(═NR6b), and each ring or ring system may be optionally substituted with one or more substituents independently selected from R17;
wherein, R17 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, —OR12, —NR13R14, nitro, —SH, —SCN, —COR15, —C(═O)OR12, —C(═O)NR13R14, —NR13C(═O)R15, —O(C═O)R15, —O(C═O)NR13R14, —C(═NOR13)R15, —NR13SO2R16, -CSR16, —C(═S)OR12, —C(═S)NR13R14, —NR13C(═S)R5, —O(C═S)R15, —O(C═S)NR13R14, —O(C═S)SR16, —N═C(R15)2, —NHCN, —SO2NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO2NR12R13, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkyl-C3-C8-cycloalkyl, C3-C8-halocycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkyl-C1-C6-thioalkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-haloalkylamino-C1-C6-alkyl, C3-C8-cycloalkylamino, C3-C8-cycloalkylamino-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, C3-C8-halocycloalkoxy, C3-C8-cycloalkyl-C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkylcarbonylalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfinyl, tri-C1-C6-alkylsilyl, C1-C6-alkylsulfonylamino, C1-C6-haloalkylsulfonylamino, C1-C6-alkylcarbonylthio, C1-C6-alkylsulfonyloxy, C1-C6-alkylsulfinyloxy, C6-C1-arylsulfonyloxy, C6-C10-arylsulfinyloxy, C6-C10-arylsulfonyl, C6-C10-arylsulfinyl, C6-C10-arylthio, C1-C6-cyanoalkyl, C2-C6-alkenylcarbonyloxy, C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-alkylthio-C1-C6-alkoxy, C2-C6-haloalkenylcarbonyloxy, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxy-C2-C6-alkynyl, C2-C6-alkynylthio, C3-C8-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C8-cycloalkyl-C1-C6-alkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl-C1-C6-alkylamino, C1-C6-haloalkylcarbonyl-C1-C6-alkylamino, C1-C6-alkoxycarbonyl-C1-C6-alkylamino, C2-C6-alkenylthio, C1-C6-alkoxy-C1-C6-alkylcarbonyl, C1-C6-haloalkoxycarbonylamino, di(C1-C6-haloalkyl)amino-C1-C6-alkyl, C3-C8-halocycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy(C1-C6-alkyl)aminocarbonyl, C1-C6-haloalkylsulfonylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, C1-C6-alkoxycarbonylalkoxy, C1-C6-alkylaminothiocarbonylamino, C3-C8-cycloalkyl-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-alkylthiocarbonyl, C3-C8-cycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxycarbonyl, di-C1-C6-alkylaminothiocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-haloalkoxy, C3-C8-halocycloalkoxy-C1-C6-alkyl, di-C1-C6-alkylaminocarbonylamino, C1-C6-alkoxy-C2-C6-alkenyl, C1-C6-alkylthiocarbonyloxy, C1-C6-haloalkoxy-C1-C6-alkoxy, C1-C6-haloalkylsulfonyloxy, C1-C6-alkoxy-C1-C6-haloalkyl, di(C1-C6-haloalkyl)amino, di-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylaminocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkylamino, tri-C1-C6-alkylsilyl-C2-C6-alkynyloxy, tri-C1-C6-alkylsilyloxy, tri-C1-C6-alkylsilyl-C2-C6-alkynyl, cyano(C1-C6-alkoxy)-C1-C6-alkyl, di-C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkoxysulfonyl, C3-C8-halocycloalkoxycarbonyl, C1-C6-alkyl-C3-C8-cycloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6-alkynyloxycarbonyl, C1-C6-cyanoalkoxycarbonyl, C1-C6-alkylthio-C1-C6-alkoxycarbonyl, C2-C6-alkynylcarbonyloxy, C2-C6-haloalkynylcarbonyloxy, cyanocarbonyloxy, C1-C6-cyanoalkylcarbonyloxy, C3-C8-cycloalkylsulphonyloxy, C3-C8-cycloalkyl-C1-C6-alkylsulphonyloxy, C3-C8-halocycloalkylsulphonyloxy, C2-C6-alkenylsulphonyloxy, C2-C6-alkynylsulphonyloxy, C1-C6-cyanoalkylsulphonyloxy, C2-C6-haloalkenylsulphonyloxy, C2-C6-haloalkynylsulphonyloxy, C2-C6-alkynylcycloalkyloxy, C2-C6-cyanoalkenyloxy, C2-C6-cyanoalkynyloxy, C1-C6-alkoxycarbonyloxy, C2-C6-alkenyloxycarbonyloxy, C2-C6-alkynyloxycarbonyloxy, C1-C6-alkoxy-C1-C6-alkylcarbonyloxy, sulfilimines, sulfoximines, SF5 and Z2Q2;
R9 and R10; and or R9 and RA together with the atoms to which they are attached may form a 3- to 10-membered carbocyclic ring or ring system, or heterocyclic ring or ring system which may be optionally substituted with R17;
wherein,
R12 is selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,
R13 and R14 are independently selected from the group consisting of hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,
R15 is selected from the group consisting of hydrogen, hydroxy, halogen, NRbRc, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl and C3-C8-cycloalkyl, and
R16 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-cycloalkyl and C3-C8-cycloalkyl;
or N-oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof.
15. The compound of claim 14, wherein L2 is the fragment of formula L2a.
16. The compound of claim 14, wherein L2 is the fragment of formula L2b.
17. A compound of Formula Ib;
Figure US20220169621A1-20220602-C00295
L1 is a direct bond, —CR2R3—, —C(═O)—, —O—, —S(═O)0-2—, —NR4— or —CR2R3C(═O)—, wherein, an expression “-” at the start and the end of the group indicates the point of attachment to either oxadiazole ring or A;
A is an aromatic or non-aromatic 5- or 6-membered carbocyclic ring, wherein the ring members of the non-aromatic carbocyclic ring are selected from C, C(═O), C(═S), C(═CR2aR3a) and C═NR6; or
A is an aromatic or non-aromatic 5- or 6-membered heterocyclic ring; wherein the heteroatom of the aromatic heterocyclic ring is selected from N, O and S; wherein heteroatom of the non-aromatic heterocyclic ring is selected from N, O, S(═O)0-2, and S(═O)0-1(═NR6) and one or more C atoms of the non-aromatic heterocyclic ring may be optionally replaced by C(═O), C(═S), C(═CR2aR3a) and C═NR6; and
wherein, A is unsubstituted or is substituted with one or more identical or different RA groups,
wherein, RA is selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, SF5, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio and C1-C6-haloalkylsulfinyl;
wherein, RA may be optionally substituted with one or more identical or different Ra selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
or
two RA together with the atoms to which they are attached may form a 3- to 10-membered aromatic or non-aromatic carbocyclic ring or ring system, or aromatic or non-aromatic heterocyclic ring or ring system which may be optionally substituted with one or more identical or different Ra,
R4, R6, R6a, R6b, and R6c are independently selected from the group of hydrogen, cyano, hydroxy, NRbRc, (C═O)—Rd, S(O)0-2Re, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, tri-C1-C6-alkylamino and C3-C8-cycloalkyl;
Rb and Rc are independently selected from the group of hydrogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C3-C8-cycloalkyl or C3-C8-halocycloalkyl,
Rd is selected from the group of hydrogen, hydroxy, halogen, NRbRc, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl and C3-C8-halocycloalkyl; and
Re is selected from the group of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl and C3-C8-halocycloalkyl;
L2 is a fragment selected from the group of
Figure US20220169621A1-20220602-C00296
wherein, k is an integer ranging from 0 to 4; an expression “#” indicates the point of attachment;
wherein, in Formula I when R1 is CF3; A is phenyl ring or C3-C7 carbocyclic ring or 5- to 6-membered heterocyclic ring; L2 is L2a wherein S atom of L2a is attached to A, and k=0 then R10 is not hydrogen, cyano, nitro, C1-C3alkyl or C1-C3 haloalkyl;
wherein, in Formula I when R1 is CF3; A is phenyl ring or 5- to 6-membered heteroaromatic ring L2 is L2b wherein S atom of L2b is attached to A, and k=0 to 4 then R10 is not cyano, nitro, R11 and OR11; wherein, R11 is hydrogen, C1-C6-alkyl optionally substituted with a group selected from halogen, cyano, nitro, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, and phenyl ring optionally substituted with C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
R2, R3, R2a, R3a, R2b, R3b, R2c, R3c, R2d, R3d, R2e, R3e, R7 and R8 are independently selected from hydrogen, halogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; or
R2 and R3; R2a and R3a; R2b and R3b; R2c and R3c; R2d and R3d; R2e and R3e; and or R7 and R8 together with the atoms to which they are attached may form 3- to 5-membered non-aromatic carbocylic ring or heterocyclic ring which may be optionally substituted with halogen, C1-C2-alkyl, C1-C2-haloalkyl or C1-C2-alkoxy;
R9 is selected from the group consisting of hydrogen; NRgRh, wherein, Rg and Rhindependently represent hydrogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C3-C8-cycloalkyl; (C═O)—Ri, wherein, Ri represents hydrogen, halogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy; C1-8-alkyl-S(O)0-2Rj, wherein Rj represents hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl; C1-C6-alkyl-(C═O)—Ri, CRi═NRg, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C4-C8-cycloalkenyl, C5-C8-cycloalkynyl, C7-C19-aralkyl;
wherein, R9 may optionally be substituted with one or more identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkoxycarbonyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl and di-C1-C6-alkylaminocarbonyl;
R10 is selected from the group consisting of halogen, hydroxy, cyano, —OR12, —NR13R14, nitro, —SH, —SCN, —COR15, —C(═O)OR12, —C(═O)NR13R14, —NR13C(═O)R15, —O(C═O)R15, —O(C═O)NR13R14, —C(═NOR13)R15, —NR13SO2R16, —CSR16, —C(═S)OR12, —C(═S)NR13R14, —NR13C(═S)R15, —O(C═S)R15, —O(C═S)NR13R14, —O(C═S)SR16, —N═C(R15)2, —NHCN, —SO2NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO2NR12R13, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkyl-C3-C8-cycloalkyl, C3-C8-halocycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkyl-C1-C6-thioalkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-haloalkylamino-C1-C6-alkyl, C3-C8-cycloalkylamino, C3-C8-cycloalkylamino-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, C3-C8-halocycloalkoxy, C3-C8-cycloalkyl-C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkylcarbonylalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfinyl, tri-C1-C6-alkylsilyl, C1-C6-alkylsulfonylamino, C1-C6-haloalkylsulfonylamino, C1-C6-alkylcarbonylthio, C1-C6-alkylsulfonyloxy, C1-C6-alkylsulfinyloxy, C6-C10-arylsulfonyloxy, C6-C10-arylsulfinyloxy, C6-C10-arylsulfonyl, C6-C10-arylsulfinyl, C6-C10-arylthio, C1-C6-cyanoalkyl, C2-C6-alkenylcarbonyloxy, C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-alkylthio-C1-C6-alkoxy, C2-C6-haloalkenylcarbonyloxy, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxy-C2-C6-alkynyl, C2-C6-alkynylthio, C3-C8-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C8-cycloalkyl-C1-C6-alkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl-C1-C6-alkylamino, C1-C6-haloalkylcarbonyl-C1-C6-alkylamino, C1-C6-alkoxycarbonyl-C1-C6-alkylamino, C2-C6-alkenylthio, C1-C6-alkoxy-C1-C6-alkylcarbonyl, C1-C6-haloalkoxycarbonylamino, di(C1-C6-haloalkyl)amino-C1-C6-alkyl, C3-C8-halocycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy(C1-C6-alkyl)aminocarbonyl, C1-C6-haloalkylsulfonylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, C1-C6-alkoxycarbonylalkoxy, C1-C6-alkylaminothiocarbonylamino, C3-C8-cycloalkyl-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-alkylthiocarbonyl, C3-C8-cycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxycarbonyl, di-C1-C6-alkylaminothiocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-haloalkoxy, C3-C8-halocycloalkoxy-C1-C6-alkyl, di-C1-C6-alkylaminocarbonylamino, C1-C6-alkoxy-C2-C6-alkenyl, C1-C6-alkylthiocarbonyloxy, C1-C6-haloalkoxy-C1-C6-alkoxy, C1-C6-haloalkylsulfonyloxy, C1-C6-alkoxy-C1-C6-haloalkyl, di(C1-C6-haloalkyl)amino, di-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylaminocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkylamino, tri-C1-C6-alkylsilyl-C2-C6-alkynyloxy, tri-C1-C6-alkylsilyloxy, tri-C1-C6-alkylsilyl-C2-C6-alkynyl, cyano(C1-C6-alkoxy)-C1-C6-alkyl, di-C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkoxysulfonyl, C3-C8-halocycloalkoxycarbonyl, C1-C6-alkyl-C3-C8-cycloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6-alkynyloxycarbonyl, C1-C6-cyanoalkoxycarbonyl, C1-C6-alkylthio-C1-C6-alkoxycarbonyl, C2-C6-alkynylcarbonyloxy, C2-C6-haloalkynylcarbonyloxy, cyanocarbonyloxy, C1-C6-cyanoalkylcarbonyloxy, C3-C8-cycloalkylsulphonyloxy, C3-C8-cycloalkyl-C1-C6-alkylsulphonyloxy, C3-C8-halocycloalkylsulphonyloxy, C2-C6-alkenylsulphonyloxy, C2-C6-alkynylsulphonyloxy, C1-C6-cyanoalkylsulphonyloxy, C2-C6-haloalkenylsulphonyloxy, C2-C6-haloalkynylsulphonyloxy, C2-C6-alkynylcycloalkyloxy, C2-C6-cyanoalkenyloxy, C2-C6-cyanoalkynyloxy, C1-C6-alkoxycarbonyloxy, C2-C6-alkenyloxycarbonyloxy, C2-C6-alkynyloxycarbonyloxy, C1-C6-alkoxy-C1-C6-alkylcarbonyloxy, sulfilimines, sulfoximines, SF5 and Z1Q1;
Z1 and Z2 are independently a direct bond, CR2dR3d, N, O, C(O), C(S), C(═CR2dR3d) or S(O)0-2;
Q1 and Q2 are independently selected from phenyl, benzyl, naphthalenyl, a 5- or 6-membered aromatic ring, an 8- to 11-membered aromatic multi-cyclic ring system, an 8- to 11-membered aromatic fused ring system, a 5- or 6-membered heteroaromatic ring, an 8- to 11-membered heteroaromatic multi-cyclic ring system or an 8- to 11-membered heteroaromatic fused ring system; wherein the heteroatom of the heteroaromatic rings is selected from N, O or S, and each ring or ring system may be optionally substituted with one or more substituents independently selected from R17; or
Q1 and Q2 are independently selected from a 3- to 7-membered non-aromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered non-aromatic heterocyclic ring, an 8- to 15-membered non-aromatic multi-cyclic ring system, an 5- to 15 membered spirocyclic ring system, or an 8- to 15-membered non-aromatic fused ring system, wherein, the heteroatom of the non-aromatic rings is selected from N, O or S(O)0-2, and C ring member of the non-aromatic carbocylic or non-aromatic heterocyclic rings or ring systems may be replaced with C(O), C(S), C(═CR2cR3c) or C(═NR6b), and each ring or ring system may be optionally substituted with one or more substituents independently selected from R17;
wherein, R17 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, —OR12, —NR13R14, nitro, —SH, —SCN, —COR15, —C(═O)OR12, —C(═O)NR13R14, —NR13C(═O)R15, —O(C═O)R15, —O(C═O)NR13R14, —C(═NOR13)R15, —NR13SO2R16, —CSR16, —C(═S)OR12, —C(═S)NR13R14, —NR13C(═S)R15, —O(C═S)R15, —O(C═S)NR13R14, —O(C═S)SR16, —N═C(R15)2, —NHCN, —SO2NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO2NR12R13, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkyl-C3-C8-cycloalkyl, C3-C8-halocycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkyl-C1-C6-thioalkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-haloalkylamino-C1-C6-alkyl, C3-C8-cycloalkylamino, C3-C8-cycloalkylamino-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, C3-C8-halocycloalkoxy, C3-C6-cycloalkyl-C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkylcarbonylalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfinyl, tri-C1-C6-alkylsilyl, C1-C6-alkylsulfonylamino, C1-C6-haloalkylsulfonylamino, C1-C6-alkylcarbonylthio, C1-C6-alkylsulfonyloxy, C1-C6-alkylsulfinyloxy, C6-C10-arylsulfonyloxy, C6-C10-arylsulfinyloxy, C6-C10-arylsulfonyl, C6-C10-arylsulfinyl, C6-C10-arylthio, C1-C6-cyanoalkyl, C2-C6-alkenylcarbonyloxy, C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-alkylthio-C1-C6-alkoxy, C2-C6-haloalkenylcarbonyloxy, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxy-C2-C6-alkynyl, C2-C6-alkynylthio, C3-C8-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C8-cycloalkyl-C1-C6-alkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl-C1-C6-alkylamino, C1-C6-haloalkylcarbonyl-C1-C6-alkylamino, C1-C6-alkoxycarbonyl-C1-C6-alkylamino, C2-C6-alkenylthio, C1-C6-alkoxy-C1-C6-alkylcarbonyl, C1-C6-haloalkoxycarbonylamino, di(C1-C6-haloalkyl)amino-C1-C6-alkyl, C3-C8-halocycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy(C1-C6-alkyl)aminocarbonyl, C1-C6-haloalkylsulfonylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, C1-C6-alkoxycarbonylalkoxy, C1-C6-alkylaminothiocarbonylamino, C3-C8-cycloalkyl-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-alkylthiocarbonyl, C3-C8-cycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxycarbonyl, di-C1-C6-alkylaminothiocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-haloalkoxy, C3-C8-halocycloalkoxy-C1-C6-alkyl, di-C1-C6-alkylaminocarbonylamino, C1-C6-alkoxy-C2-C6-alkenyl, C1-C6-alkylthiocarbonyloxy, C1-C6-haloalkoxy-C1-C6-alkoxy, C1-C6-haloalkylsulfonyloxy, C1-C6-alkoxy-C1-C6-haloalkyl, di(C1-C6-haloalkyl)amino, di-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylaminocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkylamino, tri-C1-C6-alkylsilyl-C2-C6-alkynyloxy, tri-C1-C6-alkylsilyloxy, tri-C1-C6-alkylsilyl-C2-C6-alkynyl, cyano(C1-C6-alkoxy)-C1-C6-alkyl, di-C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkoxysulfonyl, C3-C8-halocycloalkoxycarbonyl, C1-C6-alkyl-C3-C8-cycloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6-alkynyloxycarbonyl, C1-C6-cyanoalkoxycarbonyl, C1-C6-alkylthio-C1-C6-alkoxycarbonyl, C2-C6-alkynylcarbonyloxy, C2-C6-haloalkynylcarbonyloxy, cyanocarbonyloxy, C1-C6-cyanoalkylcarbonyloxy, C3-C8-cycloalkylsulphonyloxy, C3-C8-cycloalkyl-C1-C6-alkylsulphonyloxy, C3-C8-halocycloalkylsulphonyloxy, C2-C6-alkenylsulphonyloxy, C2-C6-alkynylsulphonyloxy, C1-C6-cyanoalkylsulphonyloxy, C2-C6-haloalkenylsulphonyloxy, C2-C6-haloalkynylsulphonyloxy, C2-C6-alkynylcycloalkyloxy, C2-C6-cyanoalkenyloxy, C2-C6-cyanoalkynyloxy, C1-C6-alkoxycarbonyloxy, C2-C6-alkenyloxycarbonyloxy, C2-C6-alkynyloxycarbonyloxy, C1-C6-alkoxy-C1-C6-alkylcarbonyloxy, sulfilimines, sulfoximines, SF5 and Z2Q2;
R9 and R10; and or R9 and RA together with the atoms to which they are attached may form a 3- to 10-membered carbocyclic ring or ring system, or heterocyclic ring or ring system which may be optionally substituted with R17;
wherein,
R12 is selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,
R13 and R14 are independently selected from the group consisting of hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,
R15 is selected from the group consisting of hydrogen, hydroxy, halogen, NRbRc, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl and C3-C8-cycloalkyl, and
R16 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl and C3-C8-cycloalkyl;
or N-oxides, metal complexes, isomers, polymorphs or the agriculturally acceptable salts thereof.
18. The compound of claim 17, wherein L1 is a direct bond.
19. The compound of claim 17, wherein A is phenyl.
20. The compound of claim 17, wherein L1 is a direct bond and A is phenyl.
21. The compound of claim 17, wherein L2 is the fragment of formula L2a.
22. The compound of claim 17, wherein L2 is the fragment of formula L2b.
23. The compound of claim 17, wherein L1 is a direct bond and L2 is the fragment of formula L2a.
24. The compound of claim 17, wherein L1 is a direct bond and L2 is the fragment of formula L2b.
25. The compound of claim 17, The compound of claim 17, wherein A is phenyl and L2 is the fragment of formula L2a.
26. The compound of claim 17, The compound of claim 17, wherein A is phenyl and L2 is the fragment of formula L2b.
27. The compound of claim 17, wherein L1 is a direct bond, A is phenyl, and L2 is the fragment of formula L2a.
28. The compound of claim 17, wherein L1 is a direct bond, A is phenyl, and L2 is the fragment of formula L2b.
29. A method for producing an intermediate, the method comprising:
reacting the compound of claim 14 with hydroxyl amine hydrochloride.
30. A method for producing an intermediate, the method comprising:
reacting the compound of claim 15 with hydroxyl amine hydrochloride.
31. A method for producing an intermediate, the method comprising:
reacting the compound of claim 16 with hydroxyl amine hydrochloride.
32. Use of the compound of claim 14 for the synthesis of compound of formula (l)
Figure US20220169621A1-20220602-C00297
wherein:
R1 is C1-C2-haloalkyl;
L1 is a direct bond, —CR2R3—, —C(═O)—, —O—, —S(═O)0-2—, —NR4— or —CR2R3C(═O)—, wherein, an expression “-” at the start and the end of the group indicates the point of attachment to either oxadiazole ring or A;
A is an aromatic or non-aromatic 5- or 6-membered carbocyclic ring, wherein the ring members of the non-aromatic carbocyclic ring are selected from C, C(═O), C(═S), C(═CR2aR3a) and C═NR6; or
A is an aromatic or non-aromatic 5- or 6-membered heterocyclic ring; wherein the heteroatom of the aromatic heterocyclic ring is selected from N, O and S; wherein heteroatom of the non-aromatic heterocyclic ring is selected from N, O, S(═O)0-2, and S(═O)0-1(═NR6) and one or more C atoms of the non-aromatic heterocyclic ring may be optionally replaced by C(═O), C(═S), C(═CR2aR3a) and C═NR6; and
wherein, A is unsubstituted or is substituted with one or more identical or different RA groups,
wherein, RA is selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, SF5, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio and C1-C6-haloalkylsulfinyl;
wherein, RA may be optionally substituted with one or more identical or different Ra selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
or
two RA together with the atoms to which they are attached may form a 3- to 10-membered aromatic or non-aromatic carbocyclic ring or ring system, or aromatic or non-aromatic heterocyclic ring or ring system which may be optionally substituted with one or more identical or different Ra,
R4, R6, R6a, R6b, and R6c are independently selected from the group of hydrogen, cyano, hydroxy, NRbRc, (C═O)—Rd, S(O)0-2Re, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, tri-C1-C6-alkylamino and C3-C8-cycloalkyl;
Rb and Rc are independently selected from the group of hydrogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C3-C8-cycloalkyl or C3-C8-halocycloalkyl,
Rd is selected from the group of hydrogen, hydroxy, halogen, NRbRc, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl and C3-C8-halocycloalkyl; and
Re is selected from the group of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl and C3-C8-halocycloalkyl;
L2 is a fragment selected from the group of
Figure US20220169621A1-20220602-C00298
wherein, k is an integer ranging from 0 to 4; an expression “#” indicates the point of attachment;
wherein, in Formula I when R1 is CF3; A is phenyl ring or C3-C7 carbocyclic ring or 5- to 6-membered heterocyclic ring; L2 is L2a wherein S atom of L2a is attached to A, and k=0 then R10 is not hydrogen, cyano, nitro, C1-C3alkyl or C1-C3 haloalkyl;
wherein, in Formula I when R1 is CF3; A is phenyl ring or 5- to 6-membered heteroaromatic ring L2 is L2b, wherein S atom of L2b is attached to A, and k=0 to 4 then R10 is not cyano, nitro, R11 and OR11; wherein, R11 is hydrogen, C1-C6-alkyl optionally substituted with a group selected from halogen, cyano, nitro, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, and phenyl ring optionally substituted with C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
R2, R3, R2a, R3a, R2b, R3b, R2c, R3c, R2d, R3d, R2e, R3e, R7 and R8 are independently selected from hydrogen, halogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; or
R2 and R3; R2a and R3a; R2b and R3b; R2c and R3c; R2d and R3d; R2e and R3e; and or R7 and R8 together with the atoms to which they are attached may form 3- to 5-membered non-aromatic carbocylic ring or heterocyclic ring which may be optionally substituted with halogen, C1-C2-alkyl, C1-C2-haloalkyl or C1-C2-alkoxy;
R9 is selected from the group consisting of hydrogen; NRgRh, wherein, Rg and Rh independently represent hydrogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C3-C8-cycloalkyl; (C═O)—Ri, wherein, Ri represents hydrogen, halogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy; C1-8-alkyl-S(O)0-2Rj, wherein Rj represents hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl; C1-C6-alkyl-(C═O)—Ri, CRi═NRg, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C4-C8-cycloalkenyl, C5-C8-cycloalkynyl, C7-C19-aralkyl;
wherein, R9 may optionally be substituted with one or more identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkoxycarbonyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl and di-C1-C6-alkylaminocarbonyl;
R10 is selected from the group consisting of halogen, hydroxy, cyano, —OR12, —NR13R14, nitro, —SH, —SCN, —COR15, —C(═O)OR12, —C(═O)NR13R14, —NR13C(═O)R15, —O(C═O)R15, —O(C═O)NR13R14, —C(═NOR13)R15, —NR13SO2R16, —CSR16, —C(═S)OR12, —C(═S)NR13R14, —NR13C(═S)R15, —O(C═S)R15, —O(C═S)NR13R14, —O(C═S)SR16, —N═C(R15)2, —NHCN, —SO2NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO2NR12R13, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkyl-C3-C8-cycloalkyl, C3-C8-halocycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkyl-C1-C6-thioalkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-haloalkylamino-C1-C6-alkyl, C3-C8-cycloalkylamino, C3-C8-cycloalkylamino-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, C3-C8-halocycloalkoxy, C3-C8-cycloalkyl-C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkylcarbonylalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfinyl, tri-C1-C6-alkylsilyl, C1-C6-alkylsulfonylamino, C1-C6-haloalkylsulfonylamino, C1-C6-alkylcarbonylthio, C1-C6-alkylsulfonyloxy, C1-C6-alkylsulfinyloxy, C6-C10-arylsulfonyloxy, C6-C10-arylsulfinyloxy, C6-C10-arylsulfonyl, C6-C10-arylsulfinyl, C6-C10-arylthio, C1-C6-cyanoalkyl, C2-C6-alkenylcarbonyloxy, C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-alkylthio-C1-C6-alkoxy, C2-C6-haloalkenylcarbonyloxy, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxy-C2-C6-alkynyl, C2-C6-alkynylthio, C3-C8-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C8-cycloalkyl-C1-C6-alkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl-C1-C6-alkylamino, C1-C6-haloalkylcarbonyl-C1-C6-alkylamino, C1-C6-alkoxycarbonyl-C1-C6-alkylamino, C2-C6-alkenylthio, C1-C6-alkoxy-C1-C6-alkylcarbonyl, C1-C6-haloalkoxycarbonylamino, di(C1-C6-haloalkyl)amino-C1-C6-alkyl, C3-C8-halocycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy(C1-C6-alkyl)aminocarbonyl, C1-C6-haloalkylsulfonylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, C1-C6-alkoxycarbonylalkoxy, C1-C6-alkylaminothiocarbonylamino, C3-C8-cycloalkyl-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-alkylthiocarbonyl, C3-C8-cycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxycarbonyl, di-C1-C6-alkylaminothiocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-haloalkoxy, C3-C8-halocycloalkoxy-C1-C6-alkyl, di-C1-C6-alkylaminocarbonylamino, C1-C6-alkoxy-C2-C6-alkenyl, C1-C6-alkylthiocarbonyloxy, C1-C6-haloalkoxy-C1-C6-alkoxy, C1-C6-haloalkylsulfonyloxy, C1-C6-alkoxy-C1-C6-haloalkyl, di(C1-C6-haloalkyl)amino, di-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylaminocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkylamino, tri-C1-C6-alkylsilyl-C2-C6-alkynyloxy, tri-C1-C6-alkylsilyloxy, tri-C1-C6-alkylsilyl-C2-C6-alkynyl, cyano(C1-C6-alkoxy)-C1-C6-alkyl, di-C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkoxysulfonyl, C3-C8-halocycloalkoxycarbonyl, C1-C6-alkyl-C3-C8-cycloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6-alkynyloxycarbonyl, C1-C6-cyanoalkoxycarbonyl, C1-C6-alkylthio-C1-C6-alkoxycarbonyl, C2-C6-alkynylcarbonyloxy, C2-C6-haloalkynylcarbonyloxy, cyanocarbonyloxy, C1-C6-cyanoalkylcarbonyloxy, C3-C8-cycloalkylsulphonyloxy, C3-C8-cycloalkyl-C1-C6-alkylsulphonyloxy, C3-C8-halocycloalkylsulphonyloxy, C2-C6-alkenylsulphonyloxy, C2-C6-alkynylsulphonyloxy, C1-C6-cyanoalkylsulphonyloxy, C2-C6-haloalkenylsulphonyloxy, C2-C6-haloalkynylsulphonyloxy, C2-C6-alkynylcycloalkyloxy, C2-C6-cyanoalkenyloxy, C2-C6-cyanoalkynyloxy, C1-C6-alkoxycarbonyloxy, C2-C6-alkenyloxycarbonyloxy, C2-C6-alkynyloxycarbonyloxy, C1-C6-alkoxy-C1-C6-alkylcarbonyloxy, sulfilimines, sulfoximines, SF5 and Z1Q1;
Z1 and Z2 are independently a direct bond, CR2dR3d, N, O, C(O), C(S), C(═CR2dR3d) or S(O)0-2;
Q1 and Q2 are independently selected from phenyl, benzyl, naphthalenyl, a 5- or 6-membered aromatic ring, an 8- to 11-membered aromatic multi-cyclic ring system, an 8- to 11-membered aromatic fused ring system, a 5- or 6-membered heteroaromatic ring, an 8- to 11-membered heteroaromatic multi-cyclic ring system or an 8- to 11-membered heteroaromatic fused ring system; wherein the heteroatom of the heteroaromatic rings is selected from N, O or S, and each ring or ring system may be optionally substituted with one or more substituents independently selected from R17; or
Q1 and Q2 are independently selected from a 3- to 7-membered non-aromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered non-aromatic heterocyclic ring, an 8- to 15-membered non-aromatic multi-cyclic ring system, an 5- to 15 membered spirocyclic ring system, or an 8- to 15-membered non-aromatic fused ring system, wherein, the heteroatom of the non-aromatic rings is selected from N, O or S(O)0-2, and C ring member of the non-aromatic carbocylic or non-aromatic heterocyclic rings or ring systems may be replaced with C(O), C(S), C(═CR2cR3c) or C(═NR6b), and each ring or ring system may be optionally substituted with one or more substituents independently selected from R17;
wherein, R17 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, —OR12, —NR13R14, nitro, —SH, —SCN, —COR15, —C(═O)OR12, —C(═O)NR13R14, —NR13C(═O)R15, —O(C═O)R15, —O(C═O)NR13R14, —C(═NOR13)R15, —NR13SO2R16, —CSR16, —C(═S)OR12, —C(═S)NR13R14, —NR13C(═S)R15, —O(C═S)R15, —O(C═S)NR13R14, —O(C═S)SR16, —N═C(R15)2, —NHCN, —SO2NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO2NR12R13, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkyl-C3-C8-cycloalkyl, C3-C8-halocycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkyl-C1-C6-thioalkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-haloalkylamino-C1-C6-alkyl, C3-C8-cycloalkylamino, C3-C8-cycloalkylamino-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, C3-C8-halocycloalkoxy, C3-C8-cycloalkyl-C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkylcarbonylalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfinyl, tri-C1-C6-alkylsilyl, C1-C6-alkylsulfonylamino, C1-C6-haloalkylsulfonylamino, C1-C6-alkylcarbonylthio, C1-C6-alkylsulfonyloxy, C1-C6-alkylsulfinyloxy, C6-C10-arylsulfonyloxy, C6-C10-arylsulfinyloxy, C6-C10-arylsulfonyl, C6-C10-arylsulfinyl, C6-C10-arylthio, C1-C6-cyanoalkyl, C2-C6-alkenylcarbonyloxy, C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-alkylthio-C1-C6-alkoxy, C2-C6-haloalkenylcarbonyloxy, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxy-C2-C6-alkynyl, C2-C6-alkynylthio, C3-C8-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C8-cycloalkyl-C1-C6-alkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl-C1-C6-alkylamino, C1-C6-haloalkylcarbonyl-C1-C6-alkylamino, C1-C6-alkoxycarbonyl-C1-C6-alkylamino, C2-C6-alkenylthio, C1-C6-alkoxy-C1-C6-alkylcarbonyl, C1-C6-haloalkoxycarbonylamino, di(C1-C6-haloalkyl)amino-C1-C6-alkyl, C3-C8-halocycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy(C1-C6-alkyl)aminocarbonyl, C1-C6-haloalkylsulfonylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, C1-C6-alkoxycarbonylalkoxy, C1-C6-alkylaminothiocarbonylamino, C3-C8-cycloalkyl-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-alkylthiocarbonyl, C3-C8-cycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxycarbonyl, di-C1-C6-alkylaminothiocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-haloalkoxy, C3-C8-halocycloalkoxy-C1-C6-alkyl, di-C1-C6-alkylaminocarbonylamino, C1-C6-alkoxy-C2-C6-alkenyl, C1-C6-alkylthiocarbonyloxy, C1-C6-haloalkoxy-C1-C6-alkoxy, C1-C6-haloalkylsulfonyloxy, C1-C6-alkoxy-C1-C6-haloalkyl, di(C1-C6-haloalkyl)amino, di-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylaminocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkylamino, tri-C1-C6-alkylsilyl-C2-C6-alkynyloxy, tri-C1-C6-alkylsilyloxy, tri-C1-C6-alkylsilyl-C2-C6-alkynyl, cyano(C1-C6-alkoxy)-C1-C6-alkyl, di-C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkoxysulfonyl, C3-C8-halocycloalkoxycarbonyl, C1-C6-alkyl-C3-C8-cycloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6-alkynyloxycarbonyl, C1-C6-cyanoalkoxycarbonyl, C1-C6-alkylthio-C1-C6-alkoxycarbonyl, C2-C6-alkynylcarbonyloxy, C2-C6-haloalkynylcarbonyloxy, cyanocarbonyloxy, C1-C6-cyanoalkylcarbonyloxy, C3-C8-cycloalkylsulphonyloxy, C3-C8-cycloalkyl-C1-C6-alkylsulphonyloxy, C3-C8-halocycloalkylsulphonyloxy, C2-C6-alkenylsulphonyloxy, C2-C6-alkynylsulphonyloxy, C1-C6-cyanoalkylsulphonyloxy, C2-C6-haloalkenylsulphonyloxy, C2-C6-haloalkynylsulphonyloxy, C2-C6-alkynylcycloalkyloxy, C2-C6-cyanoalkenyloxy, C2-C6-cyanoalkynyloxy, C1-C6-alkoxycarbonyloxy, C2-C6-alkenyloxycarbonyloxy, C2-C6-alkynyloxycarbonyloxy, C1-C6-alkoxy-C1-C6-alkylcarbonyloxy, sulfilimines, sulfoximines, SF5 and Z2Q2;
R9 and R10; and or R9 and RA together with the atoms to which they are attached may form a 3- to 10-membered carbocyclic ring or ring system, or heterocyclic ring or ring system which may be optionally substituted with R17;
wherein,
R12 is selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,
R13 and R14 are independently selected from the group consisting of hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,
R15 is selected from the group consisting of hydrogen, hydroxy, halogen, NRbRc, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl and C3-C8-cycloalkyl, and
R16 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl and C3-C8-cycloalkyl.
33. Use of the compound of claim 17 for the synthesis of compound of formula (1)
Figure US20220169621A1-20220602-C00299
wherein:
R1 is C1-C2-haloalkyl;
L1 is a direct bond, —CR2R3—, —C(═O)—, —O—, —S(═O)0-2—, —NR4— or —CR2R3C(═O)—, wherein, an expression “-” at the start and the end of the group indicates the point of attachment to either oxadiazole ring or A;
A is an aromatic or non-aromatic 5- or 6-membered carbocyclic ring, wherein the ring members of the non-aromatic carbocyclic ring are selected from C, C(═O), C(═S), C(═CR2aR3a) and C═NR6; or
A is an aromatic or non-aromatic 5- or 6-membered heterocyclic ring; wherein the heteroatom of the aromatic heterocyclic ring is selected from N, O and S; wherein heteroatom of the non-aromatic heterocyclic ring is selected from N, O, S(═O)0-2, and S(═O)0-1(═NR6) and one or more C atoms of the non-aromatic heterocyclic ring may be optionally replaced by C(═O), C(═S), C(═CR2aR3a) and C═NR6; and
wherein, A is unsubstituted or is substituted with one or more identical or different RA groups,
wherein, RA is selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, SF5, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkoxycarbonyl, C1-C6-alkylthio, C1-C6-haloalkylthio and C1-C6-haloalkylsulfinyl;
wherein, RA may be optionally substituted with one or more identical or different Ra selected from halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
or
two RA together with the atoms to which they are attached may form a 3- to 10-membered aromatic or non-aromatic carbocyclic ring or ring system, or aromatic or non-aromatic heterocyclic ring or ring system which may be optionally substituted with one or more identical or different Ra,
R4, R6, R6a, R6b, and R6c are independently selected from the group of hydrogen, cyano, hydroxy, NRbRc, (C═O)—Rd, S(O)0-2Re, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, tri-C1-C6-alkylamino and C3-C8-cycloalkyl;
Rb and Rc are independently selected from the group of hydrogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C3-C8-cycloalkyl or C3-C8-halocycloalkyl,
Rd is selected from the group of hydrogen, hydroxy, halogen, NRbRc, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl and C3-C8-halocycloalkyl; and
Re is selected from the group of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl and C3-C8-halocycloalkyl;
L2 is a fragment selected from the group of
Figure US20220169621A1-20220602-C00300
wherein, k is an integer ranging from 0 to 4; an expression “#” indicates the point of attachment;
wherein, in Formula I when R1 is CF3; A is phenyl ring or C3-C7 carbocyclic ring or 5- to 6-membered heterocyclic ring; L2 is L2a wherein S atom of L2a is attached to A, and k=0 then R10 is not hydrogen, cyano, nitro, C1-C3alkyl or C1-C3 haloalkyl;
wherein, in Formula I when R1 is CF3; A is phenyl ring or 5- to 6-membered heteroaromatic ring L2 is L2b, wherein S atom of L2b is attached to A, and k=0 to 4 then R10 is not cyano, nitro, R11 and OR11; wherein, R11 is hydrogen, C1-C6-alkyl optionally substituted with a group selected from halogen, cyano, nitro, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, and phenyl ring optionally substituted with C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy;
R2, R3, R2a, R3, R2b, R3b, R2c, R3c, R2d, R3d, R2e, R3e, R7 and R8 are independently selected from hydrogen, halogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; or
R2 and R3; R2a and R3a; R2b and R3b; R2c and R3c; R2d and R3d; R2e and R3e; and or R7 and R8 together with the atoms to which they are attached may form 3- to 5-membered non-aromatic carbocylic ring or heterocyclic ring which may be optionally substituted with halogen, C1-C2-alkyl, C1-C2-haloalkyl or C1-C2-alkoxy;
R9 is selected from the group consisting of hydrogen; NRgRh, wherein, Rg and Rh independently represent hydrogen, hydroxyl, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C3-C8-cycloalkyl; (C═O)—Ri, wherein, Ri represents hydrogen, halogen, cyano, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-alkoxy, and C1-C4-haloalkoxy; C1-8-alkyl-S(O)0-2Rj, wherein Rj represents hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl; C1-C6-alkyl-(C═O)—Ri, CRi═NRg, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C4-C8-cycloalkenyl, C5-C8-cycloalkynyl, C7-C19-aralkyl;
wherein, R9 may optionally be substituted with one or more identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkylalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-hydroxyalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-haloalkoxycarbonyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl and di-C1-C6-alkylaminocarbonyl;
R10 is selected from the group consisting of halogen, hydroxy, cyano, —OR12, —NR13R14, nitro, —SH, —SCN, —COR15, —C(═O)OR12, —C(═O)NR13R14, —NR13C(═O)R15, —O(C═O)R15, —O(C═O)NR13R14, —C(═NOR13)R15, —NR13SO2R16, —CSR16, —C(═S)OR12, —C(═S)NR13R14, —NR13C(═S)R15, —O(C═S)R15, —O(C═S)NR13R14, —O(C═S)SR16, —N═C(R15)2, —NHCN, —SO2NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO2NR12R13, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkyl-C3-C8-cycloalkyl, C3-C8-halocycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkyl-C1-C6-thioalkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-haloalkylamino-C1-C6-alkyl, C3-C8-cycloalkylamino, C3-C8-cycloalkylamino-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, C3-C8-halocycloalkoxy, C3-C8-cycloalkyl-C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkylcarbonylalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfinyl, tri-C1-C6-alkylsilyl, C1-C6-alkylsulfonylamino, C1-C6-haloalkylsulfonylamino, C1-C6-alkylcarbonylthio, C1-C6-alkylsulfonyloxy, C1-C6-alkylsulfinyloxy, C6-C10-arylsulfonyloxy, C6-C10-arylsulfinyloxy, C6-C10-arylsulfonyl, C6-C10-arylsulfinyl, C6-C10-arylthio, C1-C6-cyanoalkyl, C2-C6-alkenylcarbonyloxy, C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-alkylthio-C1-C6-alkoxy, C2-C6-haloalkenylcarbonyloxy, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxy-C2-C6-alkynyl, C2-C6-alkynylthio, C3-C8-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C8-cycloalkyl-C1-C6-alkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl-C1-C6-alkylamino, C1-C6-haloalkylcarbonyl-C1-C6-alkylamino, C1-C6-alkoxycarbonyl-C1-C6-alkylamino, C2-C6-alkenylthio, C1-C6-alkoxy-C1-C6-alkylcarbonyl, C1-C6-haloalkoxycarbonylamino, di(C1-C6-haloalkyl)amino-C1-C6-alkyl, C3-C8-halocycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy(C1-C6-alkyl)aminocarbonyl, C1-C6-haloalkylsulfonylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, C1-C6-alkoxycarbonylalkoxy, C1-C6-alkylaminothiocarbonylamino, C3-C8-cycloalkyl-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-alkylthiocarbonyl, C3-C8-cycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxycarbonyl, di-C1-C6-alkylaminothiocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-haloalkoxy, C3-C8-halocycloalkoxy-C1-C6-alkyl, di-C1-C6-alkylaminocarbonylamino, C1-C6-alkoxy-C2-C6-alkenyl, C1-C6-alkylthiocarbonyloxy, C1-C6-haloalkoxy-C1-C6-alkoxy, C1-C6-haloalkylsulfonyloxy, C1-C6-alkoxy-C1-C6-haloalkyl, di(C1-C6-haloalkyl)amino, di-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylaminocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkylamino, tri-C1-C6-alkylsilyl-C2-C6-alkynyloxy, tri-C1-C6-alkylsilyloxy, tri-C1-C6-alkylsilyl-C2-C6-alkynyl, cyano(C1-C6-alkoxy)-C1-C6-alkyl, di-C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkoxysulfonyl, C3-C8-halocycloalkoxycarbonyl, C1-C6-alkyl-C3-C8-cycloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6-alkynyloxycarbonyl, C1-C6-cyanoalkoxycarbonyl, C1-C6-alkylthio-C1-C6-alkoxycarbonyl, C2-C6-alkynylcarbonyloxy, C2-C6-haloalkynylcarbonyloxy, cyanocarbonyloxy, C1-C6-cyanoalkylcarbonyloxy, C3-C8-cycloalkylsulphonyloxy, C3-C8-cycloalkyl-C1-C6-alkylsulphonyloxy, C3-C8-halocycloalkylsulphonyloxy, C2-C6-alkenylsulphonyloxy, C2-C6-alkynylsulphonyloxy, C1-C6-cyanoalkylsulphonyloxy, C2-C6-haloalkenylsulphonyloxy, C2-C6-haloalkynylsulphonyloxy, C2-C6-alkynylcycloalkyloxy, C2-C6-cyanoalkenyloxy, C2-C6-cyanoalkynyloxy, C1-C6-alkoxycarbonyloxy, C2-C6-alkenyloxycarbonyloxy, C2-C6-alkynyloxycarbonyloxy, C1-C6-alkoxy-C1-C6-alkylcarbonyloxy, sulfilimines, sulfoximines, SF5 and Z1Q1;
Z1 and Z2 are independently a direct bond, CR2dR3d, N, O, C(O), C(S), C(═CR2dR3d) or S(O)0-2;
Q1 and Q2 are independently selected from phenyl, benzyl, naphthalenyl, a 5- or 6-membered aromatic ring, an 8- to 11-membered aromatic multi-cyclic ring system, an 8- to 11-membered aromatic fused ring system, a 5- or 6-membered heteroaromatic ring, an 8- to 11-membered heteroaromatic multi-cyclic ring system or an 8- to 11-membered heteroaromatic fused ring system; wherein the heteroatom of the heteroaromatic rings is selected from N, O or S, and each ring or ring system may be optionally substituted with one or more substituents independently selected from R17; or
Q1 and Q2 are independently selected from a 3- to 7-membered non-aromatic carbocyclic ring, a 4-, 5-, 6- or 7-membered non-aromatic heterocyclic ring, an 8- to 15-membered non-aromatic multi-cyclic ring system, an 5- to 15 membered spirocyclic ring system, or an 8- to 15-membered non-aromatic fused ring system, wherein, the heteroatom of the non-aromatic rings is selected from N, O or S(O)0-2, and C ring member of the non-aromatic carbocylic or non-aromatic heterocyclic rings or ring systems may be replaced with C(O), C(S), C(═CR2cR3c) or C(═NR6b), and each ring or ring system may be optionally substituted with one or more substituents independently selected from R17;
wherein, R17 is selected from the group consisting of hydrogen, halogen, hydroxy, cyano, —OR12, —NR13R14, nitro, —SH, —SCN, —COR15, —C(═O)OR12, —C(═O)NR13R14, —NR13C(═O)R15, —O(C═O)R15, —O(C═O)NR13R14, —C(═NOR13)R15, —NR13SO2R16, —CSR16, —C(═S)OR12, —C(═S)NR13R14, —NR13C(═S)R15, —O(C═S)R15, —O(C═S)NR13R14, —O(C═S)SR16, —N═C(R15)2, —NHCN, —SO2NHCN, —C(═O)NHCN, —C(═S)NHCN, —C(═S(O))NHCN, —SO2NR12R13, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkyl-C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkyl-C3-C8-cycloalkyl, C3-C8-halocycloalkyl-C1-C6-alkyl, C1-C6-alkyl-C3-C8-cycloalkyl-C1-C6-alkyl, C3-C8-cycloalkenyl, C3-C8-halocycloalkenyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkyl-C1-C6-thioalkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylamino-C1-C6-alkyl, di-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-haloalkylamino-C1-C6-alkyl, C3-C8-cycloalkylamino, C3-C8-cycloalkylamino-C1-C6-alkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkoxy-C1-C6-alkyl, C1-C6-hydroxyalkyl, C2-C6-hydroxyalkenyl, C2-C6-hydroxyalkynyl, C3-C8-halocycloalkoxy, C3-C8-cycloalkyl-C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkylcarbonylalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfinyl, tri-C1-C6-alkylsilyl, C1-C6-alkylsulfonylamino, C1-C6-haloalkylsulfonylamino, C1-C6-alkylcarbonylthio, C1-C6-alkylsulfonyloxy, C1-C6-alkylsulfinyloxy, C6-C10-arylsulfonyloxy, C6-C10-arylsulfinyloxy, C6-C10-arylsulfonyl, C6-C10-arylsulfinyl, C6-C10-arylthio, C1-C6-cyanoalkyl, C2-C6-alkenylcarbonyloxy, C1-C6-alkoxy-C1-C6-alkylthio, C1-C6-alkylthio-C1-C6-alkoxy, C2-C6-haloalkenylcarbonyloxy, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxy-C2-C6-alkynyl, C2-C6-alkynylthio, C3-C8-halocycloalkylcarbonyloxy, C2-C6-alkenylamino, C2-C6-alkynylamino, C1-C6-haloalkylamino, C3-C8-cycloalkyl-C1-C6-alkylamino, C1-C6-alkoxyamino, C1-C6-haloalkoxyamino, C1-C6-alkoxycarbonylamino, C1-C6-alkylcarbonyl-C1-C6-alkylamino, C1-C6-haloalkylcarbonyl-C1-C6-alkylamino, C1-C6-alkoxycarbonyl-C1-C6-alkylamino, C2-C6-alkenylthio, C1-C6-alkoxy-C1-C6-alkylcarbonyl, C1-C6-haloalkoxycarbonylamino, di(C1-C6-haloalkyl)amino-C1-C6-alkyl, C3-C8-halocycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy(C1-C6-alkyl)aminocarbonyl, C1-C6-haloalkylsulfonylaminocarbonyl, C1-C6-alkylsulfonylaminocarbonyl, C1-C6-alkoxycarbonylalkoxy, C1-C6-alkylaminothiocarbonylamino, C3-C8-cycloalkyl-C1-C6-alkylamino-C1-C6-alkyl, C1-C6-alkylthiocarbonyl, C3-C8-cycloalkenyloxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkoxycarbonyl, di-C1-C6-alkylaminothiocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-haloalkoxy, C3-C8-halocycloalkoxy-C1-C6-alkyl, di-C1-C6-alkylaminocarbonylamino, C1-C6-alkoxy-C2-C6-alkenyl, C1-C6-alkylthiocarbonyloxy, C1-C6-haloalkoxy-C1-C6-alkoxy, C1-C6-haloalkylsulfonyloxy, C1-C6-alkoxy-C1-C6-haloalkyl, di(C1-C6-haloalkyl)amino, di-C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylaminocarbonylamino, C1-C6-haloalkoxy-C1-C6-haloalkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkylamino, tri-C1-C6-alkylsilyl-C2-C6-alkynyloxy, tri-C1-C6-alkylsilyloxy, tri-C1-C6-alkylsilyl-C2-C6-alkynyl, cyano(C1-C6-alkoxy)-C1-C6-alkyl, di-C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkoxysulfonyl, C3-C8-halocycloalkoxycarbonyl, C1-C6-alkyl-C3-C8-cycloalkylcarbonyl, C3-C8-halocycloalkylcarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6-alkynyloxycarbonyl, C1-C6-cyanoalkoxycarbonyl, C1-C6-alkylthio-C1-C6-alkoxycarbonyl, C2-C6-alkynylcarbonyloxy, C2-C6-haloalkynylcarbonyloxy, cyanocarbonyloxy, C1-C6-cyanoalkylcarbonyloxy, C3-C6-cycloalkylsulphonyloxy, C3-C8-cycloalkyl-C1-C6-alkylsulphonyloxy, C3-C8-halocycloalkylsulphonyloxy, C2-C6-alkenylsulphonyloxy, C2-C6-alkynylsulphonyloxy, C1-C6-cyanoalkylsulphonyloxy, C2-C6-haloalkenylsulphonyloxy, C2-C6-haloalkynylsulphonyloxy, C2-C6-alkynylcycloalkyloxy, C2-C6-cyanoalkenyloxy, C2-C6-cyanoalkynyloxy, C1-C6-alkoxycarbonyloxy, C2-C6-alkenyloxycarbonyloxy, C2-C6-alkynyloxycarbonyloxy, C1-C6-alkoxy-C1-C6-alkylcarbonyloxy, sulfilimines, sulfoximines, SF5 and Z2Q2;
R9 and R10; and or R9 and RA together with the atoms to which they are attached may form a 3- to 10-membered carbocyclic ring or ring system, or heterocyclic ring or ring system which may be optionally substituted with R17;
wherein,
R12 is selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,
R13 and R14 are independently selected from the group consisting of hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,
R15 is selected from the group consisting of hydrogen, hydroxy, halogen, NRbRc, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl and C3-C8-cycloalkyl, and
R16 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl and C3-C8-cycloalkyl.
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