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WO2022058580A1 - Composés microbiocides - Google Patents

Composés microbiocides Download PDF

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Publication number
WO2022058580A1
WO2022058580A1 PCT/EP2021/075770 EP2021075770W WO2022058580A1 WO 2022058580 A1 WO2022058580 A1 WO 2022058580A1 EP 2021075770 W EP2021075770 W EP 2021075770W WO 2022058580 A1 WO2022058580 A1 WO 2022058580A1
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WIPO (PCT)
Prior art keywords
alkyl
methyl
formula
compounds
compound
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Application number
PCT/EP2021/075770
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English (en)
Inventor
Stefano RENDINE
Matthias Weiss
Simon Williams
Thomas James HOFFMAN
Original Assignee
Syngenta Crop Protection Ag
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Publication date
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Priority to BR112023004833A priority Critical patent/BR112023004833A2/pt
Publication of WO2022058580A1 publication Critical patent/WO2022058580A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring

Definitions

  • the present invention relates to microbiocidal oxime derivatives, e.g., as active ingredients, which have microbiocidal activity, in particular, fungicidal activity.
  • the invention also relates to agrochemical compositions which comprise at least one of the oxime derivatives, to processes of preparation of these compounds and to uses of the oxime derivatives or compositions in agriculture or horticulture for controlling or preventing infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, preferably fungi.
  • a compound of formula (I) wherein Y is CH or N; X is O or NH; R 1 is selected from the group consisting of hydrogen, halogen, C 1 -C 4 alkyl and C 1 -C 4 alkoxy; R 2 is selected from the group consisting of hydrogen, C 1 -C 8 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, cyanoC 1 - C 6 alkyl-, C 1 -C 6 haloalkyl, C 3 -C 6 haloalkenyl, hydroxyC 2 -C 6 alkyl-, C 1 -C 4 alkoxyC 2 -C 6 alkyl-, C 1 - C 4 haloalkoxyC 2 -C 6 alkyl-, C 1 -C 4 alkoxyC 2 -C 4 alkoxyC 2 -C 6 alkyl-, C 2 -C 6 alkenyloxyC 2
  • an agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) and an agrochemically- acceptable diluent or carrier.
  • Such an agricultural composition may further comprise at least one additional active ingredient.
  • a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms wherein a fungicidally effective amount of a compound of formula (I), or a composition comprising this compound as active ingredient, is applied to the plants, to parts thereof or the locus thereof.
  • a compound of formula (I) as a fungicide.
  • the use may exclude methods for the treatment of the human or animal body by surgery or therapy.
  • halogen or “halo” refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine or bromine.
  • cyano means a -CN group.
  • hydroxyl or “hydroxy” means an -OH group.
  • amino means an -NH 2 group.
  • C 1 -C 8 alkyl refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from one to eight carbon atoms, and which is attached to the rest of the molecule by a single bond.
  • C 1 -C 4 alkyl is to be construed accordingly.
  • C 1 -C 8 alkyl examples include, but are not limited to, methyl, ethyl, n-propyl, 1- methylethyl (iso-propyl), n-butyl, and 1-dimethylethyl (t-butyl).
  • cyanoC 1 -C 6 alkyl- refers to a C 1 -C 6 alkyl radical as generally defined above substituted by one or more cyano groups.
  • hydroxyC 2 -C 6 alkyl- refers to a C 2 -C 6 alkyl radical as generally defined above substituted by one or more hydroxy groups.
  • C 1 -C 4 alkoxy refers to a radical of the formula -ORa where Ra is a C 1 -C 4 alkyl radical as generally defined above.
  • Examples of C 1 -C 4 alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, iso-propoxy and t-butoxy.
  • C 1 -C 4 alkoxyC 2 -C 6 alkyl- refers to radical of the formula R a -O-R b - where R a is a C 1 -C 4 alkyl radical as generally defined above, and Rb is a C 2 -C 6 alkylene radical as generally defined above.
  • C 1 -C 6 haloalkyl refers to a C 1 -C 6 alkyl radical, as generally defined above, substituted by one or more of the same or different halogen atoms.
  • Examples of C 1 -C 6 haloalkyl include, but are not limited to chloromethyl, fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl and 2,2,2- trifluoroethyl.
  • C 1 -C 4 haloalkoxy refers to a C 1 -C 4 alkoxy group, as defined above, substituted by one or more of the same or different halogen atoms.
  • C 1 -C 4 haloalkoxy examples include, but are not limited to, fluoromethoxy, difluoromethoxy, fluoroethoxy, trifluoromethoxy and trifluoroethoxy.
  • C 1 -C 4 haloalkoxyC 2 -C 6 alkyl- refers to radical of the formula Ra-O-Rb- where Ra is a C 1 -C 4 haloalkyl radical as generally defined above, and Rb is a C 2 -C 6 alkylene radical as generally defined above.
  • C 3 -C 6 alkenyl refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing at least one double bond that can be of either the (E)- or (Z)-configuration, having from three to six carbon atoms, which is attached to the rest of the molecule by a single bond.
  • Examples of C 3 -C 6 alkenyl include, but are not limited to, prop-1-enyl, allyl (prop-2-enyl) and but-1-enyl.
  • C 3 -C 6 alkynyl refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having from three to six carbon atoms, and which is attached to the rest of the molecule by a single bond.
  • Examples of C 3 -C 6 alkynyl include, but are not limited to, prop-1-ynyl and propargyl (prop-2-ynyl).
  • C 1 -C 6 alkylcarbonyl refers to a radical of the formula -C(O)Ra where Ra is a C 1 -C 6 alkyl radical as generally defined above.
  • C 1 -C 3 alkylcarbonyl is to be construed accordingly.
  • the term "C 1 -C 6 alkylcarbonylC 1 -C 6 alkyl-" refers to radical of the formula Ra-C(O)-Rb- where Ra is a C 1 -C 6 alkyl radical as generally defined above, and Rb is a C 1 -C 6 alkylene radical as generally defined above.
  • C 1 -C 4 alkoxyC 2 -C 4 alkoxy- refers to radical of the formula Ra-O-Rb-O- where Ra is a C 1 -C 4 alkyl radical as generally defined above, and Rb is a C 2 -C 4 alkyl radical as generally defined above.
  • aminoC 2 -C 6 alkyl- refers to a C 2- C 6 alkyl radical as generally defined above substituted by one or more amino groups.
  • N-C 1 -C 4 alkylamino refers to a radical of the formula RaNH- wherein Ra is a C 1 -C 4 alkyl radical as generally defined above.
  • N,N-diC 1 -C 4 alkylamino refers to a radical of the formula R a (R b )N- wherein R a and R b are the same or different C 1 -C 4 alkyl radicals as generally defined above.
  • C 1 -C 6 alkylcarbonyloxy refers to a radical of the formula - OC(O)Ra wherein Ra is a C 1 -C 6 alkyl radical as generally defined above.
  • C 1 -C 6 alkylcarbonyloxyC 2 -C 6 alkyl- refers to a radical of the formula Ra-C(O)O- Rb- where Ra is a C 1 -C 6 alkyl radical as generally defined above, and Rb is a C 2 -C 6 alkylene radical as generally defined above.
  • C 1 -C 6 alkoxycarbonylC 1 -C 6 alkyl- refers to a radical of the formula Rb-OC(O)- Ra- where R a is a C 1 -C 6 alkyl radical as generally defined above, and Rb is a C 1 -C 6 alkyl radical as generally defined above.
  • C 1 -C 6 alkylsulfanyl refers to a radical of the formula -SR a wherein R a is a C 1 - C 6 alkyl radical as generally defined above.
  • C 1 -C 6 alkylsulfinyl refers to a radical of the formula -S(O)Ra wherein Ra is a C 1 -C 6 alkyl radical as generally defined above.
  • C 1 -C 6 alkylsulfonyl refers to a radical of the formula -S(O) 2 R a wherein R a is a C 1 -C 6 alkyl radical as generally defined above.
  • C 1 -C 4 alkoxyiminoC 2 -C 4 alkyl- refers to a C 1 -C 4 alkoxyimino radical as defined above attached to the rest of the molecule by a C 2 -C 4 alkylene radical as generally defined above.
  • C 3 -C 6 cycloalkyl refers to a stable, monocyclic ring radical which is saturated or partially unsaturated and contains 3 to 6 carbon atoms.
  • C 3 - C 4 cycloalkyl is to be construed accordingly.
  • Examples of C 3 -C 6 cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • the term "C 3 -C 6 cycloalkylC 1 -C 3 alkyl-" refers to a C 3 -C 6 cycloalkyl ring as defined above attached to the rest of the molecule by a C 1 -C 3 alkylene radical as defined above.
  • the term "C 3 - C 4 cycloalkylC 1 -C 2 alkyl-” is to be construed accordingly.
  • C 3 -C 6 cycloalkylC 1 -C 3 alkyl- examples include, but are not limited to cyclopropylmethyl- and cyclobutylethyl-.
  • phenylC 1 -C 3 alkyl- refers to a phenyl ring attached to the rest of the molecule by a C 1 -C 3 alkylene radical as generally defined above.
  • heterocyclyl or “heterocyclic” refers to a stable 3- to 6-membered non-aromatic monocyclic ring radical which comprises 1, 2, or 3 heteroatoms individually selected from nitrogen, oxygen and sulfur.
  • heterocyclyl radical may be bonded to the rest of the molecule via a carbon atom or heteroatom.
  • heterocyclyl include, but are not limited to, pyrrolinyl, pyrrolidyl, tetrahydrofuryl, tetrahydrothienyl, tetrahydrothiopyranyl, piperidyl, piperazinyl, tetrahydropyranyl, dihydroisoxazolyl, dioxolanyl, morpholinyl or ⁇ -lactamyl.
  • heterocyclylC 1 -C 3 alkyl- refers to a heterocyclyl ring as defined above attached to the rest of the molecule by a C 1 -C 3 alkylene radical as generally defined above.
  • heteroaryl refers to a 5- or 6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur.
  • the heteroaryl radical may be bonded to the rest of the molecule via a carbon atom or heteroatom.
  • heteroaryl examples include, furyl, pyrrolyl, imidazolyl, thienyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl or pyridyl.
  • heteroarylC 1 -C 3 alkyl- refers to a heteroaryl ring as defined above attached to the rest of the molecule by a C 1 -C 3 alkylene radical as generally defined above.
  • the compound of formula (I) may exist as E and/or Z isomers.
  • a compound of formula (I) can be drawn in at least 4 different isomeric forms as shown below.
  • the individual isomers, or intermediates depicted below or in reaction schemes 1 to 21 may interconvert in solid state, in solution, or under exposure to light.
  • the presence of one or more possible asymmetric carbon atoms in a compound of formula (I) means that the compounds may occur in chiral isomeric forms, i.e., enantiomeric or diastereomeric forms. Also atropisomers may occur as a result of restricted rotation about a single bond.
  • Formula (I) is intended to include all those possible isomeric forms and mixtures thereof.
  • the present invention includes all those possible isomeric forms and mixtures thereof for a compound of formula (I).
  • formula (I) is intended to include all possible tautomers (including lactam-lactim tautomerism and keto-enol tautomerism) where present.
  • the present invention includes all possible tautomeric forms for a compound of formula (I).
  • the compounds of formula (I) according to the invention are in free form, in covalently hydrated form, or in salt form, e.g., an agronomically usable or agrochemically acceptable salt form.
  • N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds.
  • Y is CH or N.
  • Y is CH.
  • X is O or NH.
  • X is O.
  • R 1 is selected from the group consisting of hydrogen, halogen, C 1 -C 4 alkyl and C 1 -C 4 alkoxy.
  • R 1 is selected from the group consisting of hydrogen, halogen and C 1 -C 4 alkyl. More preferably, R 1 is selected from the group consisting of hydrogen, chloro, fluoro and C 1 -C 4 alkyl. Even more preferably, R1 is selected from the group consisting of hydrogen, fluoro and methyl. Even more preferably still, R 1 is hydrogen or methyl. Most preferably, R 1 is hydrogen.
  • R 2 is selected from the group consisting of hydrogen, C 1 -C 8 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, cyanoC 1 - C 6 alkyl-, C 1 -C 6 haloalkyl, C 3 -C 6 haloalkenyl, hydroxyC 2 -C 6 alkyl-, C 1 -C 4 alkoxyC 2 -C 6 alkyl-, C 1 - C 4 haloalkoxyC 2 -C 6 alkyl-, C 1 -C 4 alkoxyC 2 -C 4 alkoxyC 2 -C 6 alkyl-, C 2 -C 6 alkenyloxyC 2 -C 6 alkyl-, C 2 - C 6 alkynyloxyC 2 -C 6 alkyl-, aminoC 2 -C 6 alkyl-, N-C 1 -C 4 alkylaminoC 2 -C 6 alkyl-, N,
  • R 2 is selected from the group consisting of C 1 -C 8 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, cyanoC 1 - C 6 alkyl-, C 1 -C 6 haloalkyl, hydroxyC 2 -C 6 alkyl-, C 1 -C 4 alkoxyC 2 -C 6 alkyl-, C 1 -C 4 haloalkoxyC 2 -C 6 alkyl-, C 1 - C 6 alkylcarbonyloxyC 2 -C 6 alkyl-, C 1 -C 4 alkoxyiminoC 2 -C 4 alkyl-, C 3 -C 6 cycloalkyl and C 3 -C 6 cycloalkylC 1 - C 3 alkyl-, wherein said C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkylC 1 -C 3 alkyl- are optionally substitute
  • R 2 is selected from the group consisting of C 1 -C 8 alkyl and C 3 -C 6 alkynyl. Even more preferably, R 2 is selected from the group consisting of C 1 -C 4 alkyl and C 3 -C 6 alkynyl. Even more preferably still, R 2 is selected from the group consisting of methyl, ethyl and propargyl. R 3 is selected from the group consisting of methyl, ethyl, propyl, iso-propyl, chloro, fluoro, cyano, difluoromethyl, trifluoromethyl, oxo, hydroxy, methoxy, ethoxy, difluoromethoxy, and cyclopropyl.
  • R 3 is selected from the group consisting of methyl, ethyl, propyl, iso-propyl, chloro, fluoro, difluoromethyl, trifluoromethyl and cyclopropyl. More preferably, R 3 is selected from the group consisting of methyl, chloro, fluoro and trifluoromethyl. Even more preferably, R 3 is chloro or fluoro.
  • a 1 is CH 2 or O. Preferably, A 1 is CH 2 .
  • a 2 is a direct bond, CH 2 , or CH 2 CH 2 .
  • a 2 is CH 2 or CH 2 CH 2 . Most preferably A 2 is CH 2 .
  • a 1 and A 2 are CH 2 .
  • Y is CH;
  • X is O;
  • R 1 is selected from the group consisting of hydrogen, fluoro and methyl;
  • R 2 is selected from the group consisting of C 1 -C 8 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, cyanoC 1 -C 6 alkyl-, C 1 - C 6 haloalkyl, hydroxyC 2 -C 6 alkyl-, C 1 -C 4 alkoxyC 2 -C 6 alkyl-, C 1 -C 4 haloalkoxyC 2 -C 6 alkyl-, C 1 - C 6 alkylcarbonyloxyC 2 -C 6 alkyl-, C 1 -C 4 alkoxyiminoC 2 -C 4 alkyl-, C 3 -C 6 cycloalkyl and C 3 -C 6 cycloalkylC 1 - C 3 alkyl-
  • Y is CH; X is O; R 1 is hydrogen; R 2 is selected from the group consisting of C 1 -C 8 alkyl and C 3 -C 6 alkynyl; A 1 is CH 2 ; and A 2 is CH 2 .
  • Y is CH; X is O; R 1 is hydrogen; R 2 is selected from the group consisting of C 1 -C 4 alkyl and C 3 -C 6 alkynyl (preferably, methyl, ethyl and propargyl); A 1 is CH 2 ; and A 2 is CH 2 .
  • the compound according to formula (I) is selected from the group consisting of compounds 1.1 to 1.6 listed in table T1 below.
  • an intermediate of formula (IIa) wherein, Y is CH; X is O; R 1 is selected from the group consisting of hydrogen, halogen and C 1 -C 4 alkyl (preferably, hydrogen, fluoro and methyl, more preferably hydrogen); A 1 is CH 2 ; and A 2 is CH 2 ;
  • a compound of formula (IIa) as defined herein in a process for the manufacture of a compound of formula (I) as defined herein.
  • the compounds of formula (I) according to the invention may be useful for combating phytopathogenic fungi (e.g Alternaria alternata, Phakopsora pachyrhizi, Plasmopara viticola, Sclerotinia sclerotiorum or Septoria tritici also known as Mycosphaerella graminicola) containing a mutation in the mitochondrial cytochrome b conferring resistance to Qo inhibitors (e.g strobilurins such as azoxystrobin, pyraclostrobin and trifloxystrobin or fenamidone or famoxadone).
  • phytopathogenic fungi e.g Alternaria alternata, Phakopsora pachyrhizi, Plasmopara viticola, Sclerotinia sclerotiorum or Septoria tritici also known as Mycosphaerella graminicola
  • Qo inhibitors e.g strobilurins such as
  • the compounds of formula (I) according to the invention may be useful for combating phytopathogenic fungi (e.g Alternaria alternata, Plasmopara viticola, Sclerotinia sclerotiorum or Septoria tritici also known as Mycosphaerella graminicola) containing a mutation in the mitochondrial cytochrome b conferring resistance to Qo inhibitors (e.g strobilurins such as azoxystrobin, pyraclostrobin and trifloxystrobin or fenamidone or famoxadone), wherein the mutation is G143A.
  • phytopathogenic fungi e.g Alternaria alternata, Plasmopara viticola, Sclerotinia sclerotiorum or Septoria tritici also known as Mycosphaerella graminicola
  • Qo inhibitors e.g strobilurins such as azoxystrobin, pyraclostrobin and tri
  • the compounds of formula (I) according to the invention may be useful for combating phytopathogenic fungi (e.g Phakopsora pachyrhizi) containing a mutation in the mitochondrial cytochrome b conferring resistance to Qo inhibitors (e.g strobilurins such as azoxystrobin, pyraclostrobin and trifloxystrobin or fenamidone or famoxadone), wherein the mutation is F129L.
  • phytopathogenic fungi e.g Phakopsora pachyrhizi
  • Qo inhibitors e.g strobilurins such as azoxystrobin, pyraclostrobin and trifloxystrobin or fenamidone or famoxadone
  • the compounds of formula (I) according to the invention may be useful for combating phytopathogenic fungi (e.g Phakopsora pachyrhizi) containing a mutation in the mitochondrial cytochrome b conferring resistance to Qo inhibitors (e.g strobilurins such as azoxystrobin, pyraclostrobin and trifloxystrobin or fenamidone or famoxadone), wherein the mutation is Y132C.
  • phytopathogenic fungi e.g Phakopsora pachyrhizi
  • Qo inhibitors e.g strobilurins such as azoxystrobin, pyraclostrobin and trifloxystrobin or fenamidone or famoxadone
  • the invention also relates to a method of controlling or preventing infestation by phytopathogenic fungi in a plant (e.g Alternaria alternate, Phakopsora pachyrhizi Plasmopara viticola, Sclerotinia sclerotiorum or Septoria tritici also known as Mycosphaerella graminicola, preferably Phakopsora pachyrhizi), wherein said phytopathogenic fungi contains a mutation in the mitochondrial cytochrome b conferring resistance to Qo inhibitors (e.g strobliurins such as azoxystrobin, pyraclostrobin and trifloxystrobin or fenamidone or famoxadone), said method comprising applying to the plant, to parts thereof or the locus thereof, a fungicidally effective amount of a compound of formula (I) (including any one of compounds 1.1 to 1.6).
  • a plant e.g Alternaria alternate, Phakopsora pachy
  • the level of resistance and therefore the impact on the performance of the fungicide can be measured by the use of a 'Resistance Factor' (RF).
  • RF EC50 value of the resistant strain/EC50 value of the sensitive strain.
  • resistant fungal strains In order to obtain resistant fungal strains, a researcher is to locate a host crop and geographical region where the relevant resistance had been reported in literature. Leaf samples infected by the target disease are then collected from the locations/host crops and sent to a laboratory, where pure cultures would be isolated. The resistant phenotype of the fungal cultures is determined either by conducting a full dose response bioassay and comparing the bioassay results to similar bioassay results for a known susceptible strain of the same species. Alternatively the resistance genotype of the fungal strain can be determined by molecular techniques (e.g. qPCR) if the resistance mechanism for the relevant species is known.
  • molecular techniques e.g. qPCR
  • the compounds of formula (I) according to the invention can be made as shown in the following schemes 1 to 21, wherein Y, X, R 1 , R 2 , R 3 , A 1 and A 2 are as defined for a compound of formula (I), unless otherwise stated.
  • Compounds of formula (I) can be prepared from compounds of formula (II) by treatment with hydroxylamines of formula (III), or an appropriate salt thereof, optionally in the presence of a base such as sodium acetate or an acid such as acetic acid and in solvents such as ethanol, methanol or water at temperatures between 20°C and 100°C.
  • compounds of formula (I) can be prepared from compounds of formula (I-I) by treatment with an alkylating agent such of formula (IV) wherein R 2 is as described for formula (I) and R 3a is an appropriate leaving group (e.g. Cl, Br, I, OTs), optionally in the presence of a base such as sodium hydride, potassium tertbutoxide or potassium carbonate, in a solvent such as dimethylformamide or tetrahydrofuran, at temperatures between 0°C and 100°C.
  • an alkylating agent such of formula (IV) wherein R 2 is as described for formula (I) and R 3a is an appropriate leaving group (e.g. Cl, Br, I, OTs)
  • a base such as sodium hydride, potassium tertbutoxide or potassium carbonate
  • solvent such as dimethylformamide or tetrahydrofuran
  • Compounds of formula (II) can be prepared from compounds of formula (V), wherein M is a metalloid species (e.g. MgCl, ZnCl, B(OH)2 or BPin), by reaction with a compound of formula (VI), where R 4 is a halogen or pseudohalogen (e.g. Br, I, OTf), in the presence of a suitable catalyst such as palladium diacetate and optionally a supporting ligand (e.g. CatCXiumA®) and base (e.g.
  • Pd(dppf)Cl2 Pd(dppf)Cl2) and base (e.g. potassium phosphate) in solvents such as 1,4-dioxane, dimethylformamide or toluene at temperatures between 20°C and 100°C.
  • solvents such as 1,4-dioxane, dimethylformamide or toluene at temperatures between 20°C and 100°C.
  • Compounds of formula (VII) are either commercially available or compounds of formula (VII) wherein A 1 and A 2 are CH 2 can be prepared from compounds of formula (VIII) using an activating agent, such as SOCl2, in a suitable solvent such as DMF or DCM, followed by introduction of a Lewis acid, such aluminium trichloride, under an atmosphere of ethylene at pressures between 0 and 20 bar and temperatures between 20°C and 120°C.
  • an activating agent such as SOCl2
  • a suitable solvent such as DMF or DCM
  • a Lewis acid such aluminium trichloride
  • a base such as sodium acetate or an acid such as acetic acid
  • solvents such as ethanol, methanol or water at temperatures between 20°C and 100°C.
  • compounds of formula (I) can be obtained by condensation with hydroxylamine or a salt thereof, optionally in the presence of a base such as sodium acetate or an acid such as acetic acid and in solvents such as ethanol or methanol at temperatures between 20°C and 100°C followed by methylation with a reagent such dimethyl sulfate or methyl iodide in the presence of a base, such as potassium tertbutoxide, in a suitable solvent such as THF.
  • a base such as sodium acetate or an acid such as acetic acid
  • solvents such as ethanol or methanol
  • Compounds of formula (IX) can be prepared from compounds of formula (X), where R 5 is Br or I, preferably I, by treatment with methylamine in the presence of a suitable catalyst such as PEPPSI TM -IPr and a base such as potassium carbonate, in an appropriate solvent (e.g. 1,4-dioxane or dimethylformamide) under an atmosphere of carbon monoxide at pressures between 0 and 20 bar and temperatures between 20°C and 120°C.
  • a suitable catalyst such as PEPPSI TM -IPr and a base such as potassium carbonate
  • an appropriate solvent e.g. 1,4-dioxane or dimethylformamide
  • a suitable organometallic species e.g. iPrMgCl.LiCl, n-BuLi, or t-BuLi
  • a suitable solvent e.g. tetrahydrofuran or diethyl ether
  • compounds of formula (IX) wherein X is NH can be prepared from compounds of formula (IX), wherein X is O, via selective amidation using methylamine, or a suitable salt thereof, optionally in the presence of an activating agent, such as diethylaluminum chloride, in a suitable solvent such as tolune.
  • an activating agent such as diethylaluminum chloride
  • compounds of formula (I) can be prepared from compounds of formula (XI), wherein M is a metalloid species (e.g.
  • R 4 is a halogen or pseudohalogen (e.g. Br, I, OTf), in the presence of a suitable catalyst such as palladium acetate and optionally a supporting ligand (e.g. CatCXiumA®) and base (e.g. potassium phosphate) in a suitable solvent such as 1,4-dioxane, DMF, or toluene at temperatures between 20°C - 150°C.
  • a suitable catalyst such as palladium acetate and optionally a supporting ligand (e.g. CatCXiumA®) and base (e.g. potassium phosphate) in a suitable solvent such as 1,4-dioxane, DMF, or toluene at temperatures between 20°C - 150°C.
  • a suitable solvent such as 1,4-dioxane, DMF, or toluene
  • Compounds of formula (XI) wherein M is a metalloid species can be prepared from compounds of formula (X) wherein R 5 is a halogen or pseudohalogen (e.g. I, Br, Cl, OTf) by treatment with a suitable reagent (e.g. bis-pinacolatodiboron) optionally in the presence of a suitable catalyst (e.g. Pd(dppf)Cl2) and base (e.g. potassium phosphate) in a solvent such as 1,4-dioxane, dimethylformamide or toluene at temperatures between 20°C-150°C.
  • a suitable reagent e.g. bis-pinacolatodiboron
  • a suitable catalyst e.g. Pd(dppf)Cl2
  • base e.g. potassium phosphate
  • compounds of formula (XI), wherein M is a metal species can be prepared from compounds of formula (X), where R 5 is Cl, Br or I, via metal-halogen exchange with a suitable organometallic species (e.g. iPrMgCl.LiCl, n-BuLi, or EtZnCl), in a suitable solvent (e.g. tetrahydrofuran or diethyl ether), and at temperatures between -78°C and 25°C.
  • a suitable organometallic species e.g. iPrMgCl.LiCl, n-BuLi, or EtZnCl
  • a suitable solvent e.g. tetrahydrofuran or diethyl ether
  • compounds of formula (I) wherein Y is N can be obtained from compounds of formula (XII) via addition of tertbutyl nitrite in a suitable solvent, such as toluene, and optionally in the presence of a base, such as potassium tert-butoxide followed by the addition of a methylating reagent such as methyl iodie or dimethylsulfate at a suitable temperature range between 20°C and 50°C.
  • a suitable solvent such as toluene
  • a base such as potassium tert-butoxide
  • a methylating reagent such as methyl iodie or dimethylsulfate
  • a minor nitrone byproduct of formula (XIII) may form and it can be converted to compounds of formula (I) via treatment with N-methyl hydroxylamine or a salt thereof, optionally in the presence of a base and in a suitable solvent such as DMSO, MeCN, or DMF at temperatures between 50°C and 100°C.
  • a suitable solvent such as DMSO, MeCN, or DMF at temperatures between 50°C and 100°C.
  • compounds of formula (XV) wherein Y is N can be obtained from compounds of formula (XIV) via addition of an oxidant, such as tert-butyl nitrite in a suitable solvent, such as toluene, and optionally in the presence of a base, such as potassium tert-butoxide followed by the addition of a methylating reagent such as methyl iodie or dimethylsulfate at suitable temperatures between 20°C and 50°C.
  • an oxidant such as tert-butyl nitrite
  • a suitable solvent such as toluene
  • a base such as potassium tert-butoxide
  • a methylating reagent such as methyl iodie or dimethylsulfate
  • a minor nitrone byproduct of formula (XVI) may form which can be converted to a compound of formula (XV) via treatment with N-methyl hydroxylamine or a salt thereof, optionally in the presence of a base and in a suitable solvent such as DMSO, MeCN, or DMF at temperatures between 50°C and 100°C.
  • a suitable solvent such as DMSO, MeCN, or DMF at temperatures between 50°C and 100°C.
  • Compounds of formula (II) can be obtained from compounds of formula (XV), via intoduction of a suitable acid, such as trifluoroacetic acid or para-tolulsulfonic acid, in a suitable solvent, such as acetone and water. This is shown in scheme 15 and for related examples see Current Organocatalysis 2018, 5, 196-200 or Journal of Organic Chemistry, 2006, 71, 4956-4964.
  • Compounds of formula (XVII) can be obtained from compounds of formula (VII), via introductionwith ethylene glycol in the presence of a suitable acid, such as camphorsulfonic acid or para-tolylsulfonic acid, in a suitable solvent, such as toluene or methyl orthoester at temperatures between 20°C and 50°C. This is shown in scheme 17 and for related examples see WO2006044293.
  • Compounds of formula (XVIII) wherein M is a metalloid species (e.g. B(OH)2, BPin) can be prepared from compounds of formula (XVII) wherein R 5 is a halogen or pseudohalogen (e.g.
  • a suitable metallating agent e.g. bis-pinacolatodiboron
  • a suitable catalyst e.g. Pd(dppf)Cl 2
  • base e.g. potassium phosphate
  • M is a metalloid species such as (e.g.
  • ZnCl, MgCl, Li can be prepared from compounds of formula (XVII), where R 5 is Cl, Br or I, via metal-halogen exchange with a suitable organometallic species (e.g. iPrMgCl.LiCl, n-BuLi, or EtZnCl), in a suitable solvent (e.g. tetrahydrofuran or diethyl ether), and at a temperature between -78°C.
  • a suitable organometallic species e.g. iPrMgCl.LiCl, n-BuLi, or EtZnCl
  • a suitable solvent e.g. tetrahydrofuran or diethyl ether
  • Compounds of formula (XV), can be obtained from compounds of formula (XIV), by treatment with a base such as sodium methoxide and a formylating agent such as methyl formate followed by methylation with a reagent such dimethyl sulfate in the presence of a base such as K2CO3 or via introduction of ortho methylester in the presence of an acid such as H2SO4.
  • a base such as sodium methoxide and a formylating agent such as methyl formate followed by methylation with a reagent such dimethyl sulfate in the presence of a base such as K2CO3 or via introduction of ortho methylester in the presence of an acid such as H2SO4.
  • a suitable catalyst such as palladium acetate and optionally a supporting ligand (e.g. CatCXiumA®) and base (e.g. potassium phosphate) in a suitable solvent such as 1,4-dioxane, DMF or toluene at temperatures between 20°C- 150°C.
  • a suitable catalyst such as palladium acetate and optionally a supporting ligand (e.g
  • compounds of formula (XIX) wherein X is NH can be prepared from compounds of formula (XIX) wherein X is O, via selective amidation using methylamine, or a suitable salt thereof, optionally in a one pot fashion and optionally in the presence of a base.
  • a suitable salt thereof optionally in a one pot fashion and optionally in the presence of a base.
  • Such conversions may also take place after use, e. g. in the treatment of plants in the treated plant, or in the harmful fungus to be controlled.
  • the compounds of formula (I) of the present invention have, for practical purposes, a very advantageous level of biological activity for protecting plants against diseases that are caused by fungi.
  • the compounds of formula (I) can be used in the agricultural sector and related fields of use, e.g., as active ingredients for controlling plant pests or on non-living materials for the control of spoilage microorganisms or organisms potentially harmful to man.
  • the novel compounds are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe.
  • the compounds of formula (I) can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later, e.g., from phytopathogenic microorganisms.
  • the present invention further relates to a method for controlling or preventing infestation of plants or plant propagation material and/or harvested food crops susceptible to microbial attack by treating plants or plant propagation material and/or harvested food crops wherein an effective amount a compound of formula (I) is applied to the plants, to parts thereof or the locus thereof.
  • fungicide as used herein means a compound that controls, modifies, or prevents the growth of fungi.
  • fungicidally effective amount where used means the quantity of such a compound or combination of such compounds that is capable of producing an effect on the growth of fungi. Controlling or modifying effects include all deviation from natural development, such as killing, retardation and the like, and prevention includes barrier or other defensive formation in or on a plant to prevent fungal infection.
  • compounds of formula (I) as dressing agents for the treatment of plant propagation material, e.g., seed, such as fruits, tubers or grains, or plant cuttings, for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil.
  • the propagation material can be treated with a composition comprising a compound of formula (I) before planting: seed, for example, can be dressed before being sown.
  • the active compounds of formula (I) can also be applied to grains (coating), either by impregnating the seeds in a liquid formulation or by coating them with a solid formulation.
  • the composition can also be applied to the planting site when the propagation material is being planted, for example, to the seed furrow during sowing.
  • the invention relates also to such methods of treating plant propagation material and to the plant propagation material so treated.
  • the compounds of formula (I) can be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage, in hygiene management.
  • the invention could be used to protect non-living materials from fungal attack, e.g. lumber, wall boards and paint.
  • the compounds of formula (I) are for example, effective against fungi and fungal vectors of disease as well as phytopathogenic bacteria and viruses.
  • fungi and fungal vectors of disease as well as phytopathogenic bacteria and viruses are for example: Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp, Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa, Botrytis spp. comprising B. cinerea, Candida spp.
  • C. albicans including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans, Ceratocystis spp, Cercospora spp. including C. arachidicola, Cercosporidium personatum, Cladosporium spp, Claviceps purpurea, Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C.
  • Penicillium spp. including P. digitatum, P. italicum, Petriellidium spp, Peronosclerospora spp. Including P. maydis, P. philippinensis and P. sorghi, Peronospora spp, Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp, Phoma spp, Phomopsis viticola, Phytophthora spp.
  • P. infestans Plasmopara spp. including P. halstedii, P. viticola, Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp, Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopeziza tracheiphila, Puccinia Spp. including P. hordei, P. recondita, P. striiformis, P.
  • the compounds of formula (I) may be used for example on turf, ornamentals, such as flowers, shrubs, broad-leaved trees or evergreens, for example conifers, as well as for tree injection, pest management and the like.
  • target crops and/or useful plants to be protected typically comprise perennial and annual crops, such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals for example barley, maize (corn), millet, oats, rice, rye, sorghum triticale and wheat; fibre plants for example cotton, flax, hemp, jute and sisal; field crops for example sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St.
  • perennial and annual crops such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries
  • cereals for example barley, maize (corn), millet, oats
  • Augustine grass and Zoysia grass herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes for example beans, lentils, peas and soya beans; nuts for example almond, cashew, ground nut, hazelnut, peanut, pecan, pistachio and walnut; palms for example oil palm; ornamentals for example flowers, shrubs and trees; other trees, for example cacao, coconut, olive and rubber; vegetables for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vines for example grapes.
  • herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme
  • legumes for example beans, lentils, peas and soya beans
  • useful plants is to be understood as also including useful plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl- shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering.
  • herbicides like bromoxynil or classes of herbicides
  • EPSPS (5-enol-pyrovyl- shikimate-3-phosphate-synthase) inhibitors
  • GS glutamine synthetase
  • PPO protoporphyrinogen-oxidase
  • imazamox by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola).
  • crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I ⁇ and LibertyLink®.
  • Useful plants is to be understood as also including useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.
  • YieldGard ⁇ (maize variety that expresses a CryIA(b) toxin); YieldGard Rootworm ⁇ (maize variety that expresses a CryIIIB(b1) toxin); YieldGard Plus ⁇ (maize variety that expresses a CryIA(b) and a CryIIIB(b1) toxin); Starlink ⁇ (maize variety that expresses a Cry9(c) toxin); Herculex I ⁇ (maize variety that expresses a CryIF(a2) toxin and the enzyme phosphinothricine N- acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B ⁇ (cotton variety that expresses a CryIA(c) toxin); Bollgard I ⁇ (cotton variety that expresses a CryIA(c) toxin); Boll
  • crops is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.
  • Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as ⁇ - endotoxins, e.g.
  • Vip vegetative insecticidal proteins
  • Vip e.g. Vip1, Vip2, Vip3 or Vip3A
  • insecticidal proteins of bacteria colonising nematodes for example Photorhabdus spp.
  • Xenorhabdus spp. such as Photorhabdus luminescens, Xenorhabdus nematophilus
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins
  • agglutinins proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors
  • ribosome- inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecd
  • ⁇ -endotoxins for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1, Vip2, Vip3 or Vip3A
  • Vip vegetative insecticidal proteins
  • Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701).
  • Truncated toxins for example a truncated Cry1Ab, are known.
  • modified toxins one or more amino acids of the naturally occurring toxin are replaced.
  • preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G- recognition sequence is inserted into a Cry3A toxin (see WO 03/018810).
  • Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0374753, WO93/07278, WO95/34656, EP-A-0427529, EP-A-451878 and WO 03/052073.
  • transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0367 474, EP-A-0401979 and WO 90/13651.
  • the toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects.
  • Such insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).
  • Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard ⁇ (maize variety that expresses a Cry1Ab toxin); YieldGard Rootworm ⁇ (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus ⁇ (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin); Starlink ⁇ (maize variety that expresses a Cry9C toxin); Herculex I ⁇ (maize variety that expresses a Cry1Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B ⁇ (cotton variety that expresses a Cry1Ac toxin); Bollgard I
  • transgenic crops are: 1. Bt11 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium. 2. Bt176 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St.
  • This toxin is Cry3A055 modified by insertion of a cathepsin-G- protease recognition sequence.
  • the preparation of such transgenic maize plants is described in WO 03/018810.
  • MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9.
  • MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects. 5.
  • NK603 ⁇ MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
  • the compounds of formula (I) (including any one of compounds 1.1 to 1.6) or fungicidal compositions according to the present invention comprising a compound of formula (I) may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) on soy bean plants.
  • transgenic soybean plants expressing toxins for example insecticidal proteins such as delta-endotoxins, e.g. Cry1Ac (Cry1Ac Bt protein).
  • toxins for example insecticidal proteins such as delta-endotoxins, e.g. Cry1Ac (Cry1Ac Bt protein).
  • this may include transgenic soybean plants comprising event MON87701 (see U.S. Patent No. 8,049,071 and related applications and patents, as well as WO 2014/170327 A1 (eg, see paragraph [008] reference to Intacta RR2 PRO TM soybean)), event MON87751 (US. Patent Application Publication No. 2014/0373191) or event DAS- 81419 (U.S. Patent No.8632978 and related applications and patents).
  • event MON87701 see U.S. Patent No. 8,049,071 and related applications and patents, as well as WO 2014/170327 A1 (eg, see paragraph [008] reference
  • transgenic soybean plants may comprise event SYHT0H2 - HPPD tolerance (U.S. Patent Application Publication No. 2014/0201860 and related applications and patents), event MON89788 - glyphosate tolerance (U.S. Pat. No.7,632,985 and related applications and patents), event MON87708 - dicamba tolerance (U.S. Patent Application Publication No. US 2011/0067134 and related applications and patents), event DP-356043-5 - glyphosate and ALS tolerance (U.S. Patent Application Publication No. US 2010/0184079 and related applications and patents), event A2704-12 - glufosinate tolerance (U.S. Patent Application Publication No.
  • event DAS-40278-9 - tolerance to 2,4- dichlorophenoxyacetic acid and aryloxyphenoxypropionate see WO 2011/022469, WO 2011/022470, WO 2011/022471, and related applications and patents
  • event 127 - ALS tolerance WO 2010/080829 and related applications and patents
  • event GTS 40-3-2 - glyphosate tolerance event DAS-68416-4- 2,4-dichlorophenoxyacetic acid and glufosinate tolerance
  • event FG72 - glyphosate and isoxaflutole tolerance event BPS-CV127-9 - ALS tolerance and GU262 - glufosinate tolerance or event SYHT04R - HPPD tolerance.
  • the compounds of formula (I) may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) on soy bean plants.
  • phytopathogenic diseases especially phytopathogenic fungi (such as Phakopsora pachyrhizi)
  • soy bean plants there are known in the scientific literature certain Elite soybean plant varieties where R-gene stacks, conferring a degree of immunity or resistance to specific Phakopsora pachyrhizi, have been been introgressed in the plant genome, see for example: “Fighting Asian Soybean Rust”, Langenbach C, et al, Front Plant Science 7(797) 2016).
  • An elite plant is any plant from an elite line, such that an elite plant is a representative plant from an elite variety.
  • elite soybean varieties that are commercially available to farmers or soybean breeders include: AG00802, A0868, AG0902, A1923, AG2403, A2824, A3704, A4324, A5404, AG5903, AG6202 AG0934; AG1435; AG2031; AG2035; AG2433; AG2733; AG2933; AG3334; AG3832; AG4135; AG4632; AG4934; AG5831; AG6534; and AG7231 (Asgrow Seeds, Des Moines, Iowa, USA); BPR0144RR, BPR 4077NRR and BPR 4390NRR (Bio Plant Research, Camp Point, Ill., USA); DKB17- 51 and DKB37-51 (DeKalb Genetics, DeKalb, Ill., USA); DP 4546 RR, and DP 7870 RR (Delta & Pine Land Company, Lubbock,
  • the compounds of formula (I) (including any one of compounds 1.1 to 1.6), or fungicidal compositions according to the present invention comprising a compound of formula (I), are used to control Phakopsora pachyrhizi, (including fungicidally-resistant strains thereof, as outlined herein) on Elite soybean plant varieties where R-gene stacks, conferring a degree of immunity or resistance to specific Phakopsora pachyrhizi, have been been introgressed in the plant genome. Numerous benefits may be expected to ensue from said use, e.g.
  • Fungicidal-resistant strains of Phakopsora pachyrhizi have been reported in the scientific literature, with strains resistant to one or more fungicides from at least each of the following fungicidal mode of action classes being observed: sterol demethylation-inhibitors (DMI), quinone-outside-inhibitors (QoI) and succinate dehydrogenase inhibitors (SDHI).
  • DMI sterol demethylation-inhibitors
  • QoI quinone-outside-inhibitors
  • SDHI succinate dehydrogenase inhibitors
  • the compounds of formula (I) (including any one of compounds 1.1 to 1.6), or fungicidal compositions according to the present invention comprising a compound of formula (I), are used to control Phakopsora pachyrhizi which are resistant to one or more fungicides from any of the following fungicidal MoA classes: sterol demethylation-inhibitors (DMI), quinone-outside-inhibitors (QoI) and succinate dehydrogenase inhibitors (SDHI).
  • locus as used herein means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil.
  • plants refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.
  • plant propagation material is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes.
  • seeds in the strict sense
  • Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned.
  • plant propagation material is understood to denote seeds.
  • the compounds of formula (I) may be used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they may be conveniently Formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances.
  • compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
  • Suitable carriers and adjuvants e.g. for agricultural use, can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.
  • Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended.
  • Such formulations include anti-settling agents and dispersing agents and may further include a wetting agent to enhance activity as well an anti-foam and a crystal growth inhibitor.
  • these concentrates are diluted in water and normally applied as a spray to the area to be treated.
  • the amount of active ingredient may range from 0.5% to 95% of the concentrate.
  • Wettable powders are in the form of finely divided particles which disperse readily in water or other liquid carriers. The particles contain the active ingredient retained in a solid matrix.
  • Typical solid matrices include fuller’s earth, kaolin clays, silicas and other readily wet organic or inorganic solids.
  • Wettable powders normally contain from 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.
  • Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquid and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and normally applied as a spray to the area to be treated.
  • the amount of active ingredient may range from 0.5% to 95% of the concentrate.
  • Granular formulations include both extrudates and relatively coarse particles and are usually applied without dilution to the area in which treatment is required.
  • Typical carriers for granular Formulations include sand, fuller’s earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corn cobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulphate and other organic or inorganic materials which absorb or which can be coated with the active compound.
  • Granular Formulations normally contain 5% to 25% of active ingredients which may include surface-active agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils; and/or stickers such as dextrins, glue or synthetic resins.
  • Dusts are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.
  • Microcapsules are typically droplets or granules of the active ingredient enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates. Encapsulated droplets are typically 1 to 50 microns in diameter.
  • the enclosed liquid typically constitutes 50 to 95% of the weight of the capsule and may include solvent in addition to the active compound.
  • Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores.
  • Granules typically range from 1 millimetre to 1 centimetre and preferably 1 to 2 millimetres in diameter.
  • Granules are formed by extrusion, agglomeration or prilling, or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust and granular carbon.
  • Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.
  • Other useful formulations for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents.
  • Pressurised sprayers wherein the active ingredient is dispersed in finely-divided form as a result of vaporisation of a low boiling dispersant solvent carrier, may also be used.
  • Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl formamide, dimethyl sulfoxide, 1,4
  • Water is generally the carrier of choice for the dilution of concentrates.
  • suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller’s earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin.
  • a broad range of surface-active agents are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application. These agents, when used, normally comprise from 0.1% to 15% by weight of the formulation.
  • Typical surface active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C.sub.
  • soaps such as sodium stearate
  • alkylnaphthalenesulfonate salts such as sodium dibutylnaphthalenesulfonate
  • dialkyl esters of sulfosuccinate salts such as sodium di(2-ethylhexyl) sulfosuccinate
  • sorbitol esters such as sorbitol oleate
  • quaternary amines such as lauryl trimethylammonium chloride
  • polyethylene glycol esters of fatty acids such as polyethylene glycol stearate
  • block copolymers of ethylene oxide and propylene oxide and salts of mono and dialkyl phosphate esters.
  • compositions of the invention include crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, anti- foaming agents, light-blocking agents, compatibilizing agents, antifoam agents, sequestering agents, neutralising agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants and sticking agents.
  • biocidally active ingredients or compositions may be combined with the compositions of the invention and used in the methods of the invention and applied simultaneously or sequentially with the compositions of the invention.
  • these further active ingredients may be formulated together with the compositions of the invention or mixed in, for example, the spray tank.
  • These further biocidally active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and/or plant growth regulators.
  • Pesticidal agents are referred to herein using their common name are known, for example, from "The Pesticide Manual", 15th Ed., British Crop Protection Council 2009.
  • the compositions of the invention may also be applied with one or more systemically acquired resistance inducers (“SAR” inducer). SAR inducers are known and described in, for example, United States Patent No.
  • the compounds of formula (I) are normally used in the form of agrochemical compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds.
  • further compounds can be e.g. fertilizers or micronutrient donors or other preparations, which influence the growth of plants. They can also be selective herbicides or non-selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.
  • the compounds of formula (I) may be used in the form of (fungicidal) compositions for controlling or protecting against phytopathogenic microorganisms, comprising as active ingredient at least one compound of formula (I) or of at least one preferred individual compound as defined herein, in free form or in agrochemically usable salt form, and at least one of the above-mentioned adjuvants.
  • the invention therefore provides a composition, preferably a fungicidal composition, comprising at least one compound formula (I) an agriculturally acceptable carrier and optionally an adjuvant.
  • An agricultural acceptable carrier is for example a carrier that is suitable for agricultural use. Agricultural carriers are well known in the art.
  • composition may comprise at least one or more pesticidally-active compounds, for example an additional fungicidal active ingredient in addition to the compound of formula (I).
  • the compound of formula (I) may be the sole active ingredient of a composition or it may be admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate.
  • An additional active ingredient may, in some cases, result in unexpected synergistic activities.
  • Suitable additional active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenical fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fung
  • suitable additional active ingredients also include the following: 3-difluoromethyl-1-methyl- 1H-pyrazole-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)- amide , 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[1-methyl-2-(2,4,6- trichlorophenyl)-ethyl]-amide , 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (2- dichloromethylene-3-ethyl-1-methyl-indan-4-yl)-amide (1072957-71-1), 1-methyl-3-difluoromethyl-1H- pyrazole-4-carboxylic acid (4'-methylsulfanyl-biphenyl-2-yl)-amide, 1-methyl-3-difluoromethyl-4H- pyrazole-4-
  • the compounds of the invention may also be used in combination with anthelmintic agents.
  • anthelmintic agents include, compounds selected from the macrocyclic lactone class of compounds such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives as described in EP- 357460, EP-444964 and EP- 594291.
  • Additional anthelmintic agents include semisynthetic and biosynthetic avermectin/milbemycin derivatives such as those described in US-5015630, WO-9415944 and WO-9522552. Additional anthelmintic agents include the benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, and other members of the class. Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel.
  • Additional anthelmintic agents include flukicides, such as triclabendazole and clorsulon and the cestocides, such as praziquantel and epsiprantel.
  • flukicides such as triclabendazole and clorsulon
  • cestocides such as praziquantel and epsiprantel.
  • the compounds of the invention may be used in combination with derivatives and analogues of the paraherquamide/marcfortine class of anthelmintic agents, as well as the antiparasitic oxazolines such as those disclosed in US-5478855, US- 4639771 and DE-19520936.
  • the compounds of the invention may be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO 96/15121 and also with anthelmintic active cyclic depsipeptides such as those described in WO 96/11945, WO 93/19053, WO 93/25543, EP 0626375, EP 0382173, WO 94/19334, EP 0382173, and EP 0503538.
  • the compounds of the invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.
  • ectoparasiticides for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.
  • terpene alkaloids for example those described in International Patent Application Publication Numbers WO 95/19363 or WO 04/72086, particularly the compounds disclosed therein.
  • Organophosphates acephate, azamethiphos, azinphos-ethyl, azinphos- methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosthiazate, hep
  • Carbamates alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717.
  • Pyrethroids acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E) -(1 R)-cis-2,2-dimethyl-3-(2- oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta -cyfluthrin, cyfluthrin, a- cypermethrin, beta -cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, ethofenprox, fenfluthrin, fenpropathrin,
  • Arthropod growth regulators a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.
  • antiparasitics acequinocyl, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine, diacloden, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, ethofenprox, fenazaquin, flumite, MTI- 800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox, fluproxyfen, halofenprox, hydr
  • Biological agents Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, virus and fungi.
  • Bactericides chlortetracycline, oxytetracycline, streptomycin.
  • Such mixtures include (wherein “I” represents a compound of formula (I)): a compound selected from the group of substances consisting of petroleum oils + I, 1,1-bis(4-chloro-phenyl)-2-ethoxyethanol + I, 2,4-dichlorophenyl benzenesulfonate + I, 2-fluoro-N-methyl-N-1-naphthylacetamide + I, 4-chlorophenyl phenyl sulfone + I, acetoprole + I, aldoxycarb + I, amidithion + I, amidothioate + I, amiton + I, amiton hydrogen oxalate + I, amitraz + I, aramite + I, arsenous oxide + I, azobenzene + I, azothoate + I, benomyl + I, benoxa-fos + I, benzyl benzoate + I, bixafen + I, brofenval
  • the compounds in this paragraph may be prepared from the methods described in WO 2017/055473, WO 2017/055469, WO 2017/093348 and WO 2017/118689; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4- triazol-1-yl)propan-2-ol + I (this compound may be prepared from the methods described in WO 2017/029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + I (this compound may be prepared from the methods described in WO 2017/029179); 3-[2-(1- chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + I (this compound may be prepared from the methods described in WO 2016/156290); 3-[2-(
  • the designation is not a "common name”, the nature of the designation used instead is given in round brackets for the particular compound; in that case, the IUPAC name, the IUPAC/Chemical Abstracts name, a "chemical name”, a “traditional name”, a “compound name” or a “develoment code” is used or, if neither one of those designations nor a "common name” is used, an "alternative name” is employed.
  • “CAS Reg. No” means the Chemical Abstracts Registry Number.
  • the active ingredient mixture of the compounds of formula (I) and an active ingredient as described above are preferably in a mixing ratio of from 100:1 to 1:6000, especially from 50:1 to 1:50, more especially in a ratio of from 20:1 to 1:20, even more especially from 10:1 to 1:10, very especially from 5:1 and 1:5, special preference being given to a ratio of from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 being likewise preferred, above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500
  • the mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the pests or their environment, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.
  • the mixtures comprising a compound of formula (I) and one or more active ingredients as described above can be applied, for example, in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days.
  • compositions according to the invention can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.
  • auxiliaries such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides
  • compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries).
  • auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries).
  • Another aspect of the invention is related to the use of a compound of formula (I) or of a preferred individual compound as defined herein, of a composition comprising at least one compound of formula (I) or at least one preferred individual compound as above-defined, or of a fungicidal or insecticidal mixture comprising at least one compound of formula (I) or at least one preferred individual compound as above-defined, in admixture with other fungicides or insecticides as described above, for controlling or preventing infestation of plants, e.g. useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living materials by insects or by phytopathogenic microorganisms, preferably fungal organisms.
  • useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living materials by insects or by phytopathogenic microorganisms, preferably fungal organisms.
  • a further aspect of the invention is related to a method of controlling or preventing an infestation of plants, e.g., useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g., harvested food crops, or of non-living materials by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, which comprises the application of a compound of formula (I) or of a preferred individual compound as above-defined as active ingredient to the plants, to parts of the plants or to the locus thereof, to the propagation material thereof, or to any part of the non-living materials.
  • useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g., harvested food crops, or of non-living materials by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms
  • a compound of formula (I) or of a preferred individual compound as above-defined as active ingredient to the plants, to parts
  • Controlling or preventing means reducing infestation by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, to such a level that an improvement is demonstrated.
  • a preferred method of controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects which comprises the application of a compound of formula (I), or an agrochemical composition which contains at least one of said compounds, is foliar application. The frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen or insect.
  • the compounds of formula (I) can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field.
  • the compounds of formula I may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.
  • a formulation e.g.
  • compositions containing the compound of formula (I), and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of formula (I), may be prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • extenders for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • Advantageous rates of application are normally from 5g to 2kg of active ingredient (a.i.) per hectare (ha), preferably from 10g to 1kg a.i./ha, most preferably from 20g to 600g a.i./ha.
  • convenient dosages are from 10mg to 1g of active substance per kg of seeds.
  • a composition comprising a compound of formula (I) according to the present invention is applied either preventative, meaning prior to disease development or curative, meaning after disease development.
  • compositions of the invention may be employed in any conventional form, for example in the form of a twin pack, a powder for dry seed treatment (DS), an emulsion for seed treatment (ES), a flowable concentrate for seed treatment (FS), a solution for seed treatment (LS), a water dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK
  • compositions may be produced in conventional manner, e.g. by mixing the active ingredients with appropriate formulation inerts (diluents, solvents, fillers and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners and compounds that provide adjuvancy effects).
  • appropriate formulation inerts diiluents, solvents, fillers and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners and compounds that provide adjuvancy effects.
  • conventional slow release formulations may be employed where long lasting efficacy is intended.
  • Particularly formulations to be applied in spraying forms such as water dispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvancy effects, e.g.
  • a seed dressing formulation is applied in a manner known per se to the seeds employing the combination of the invention and a diluent in suitable seed dressing formulation form, e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds.
  • suitable seed dressing formulation form e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds.
  • seed dressing formulations are known in the art.
  • Seed dressing formulations may contain the single active ingredients or the combination of active ingredients in encapsulated form, e.g.
  • the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% agriculturally acceptable surfactant and 10 to 99.99% solid or liquid formulation inerts and adjuvant(s), the active agent consisting of at least the compound of formula (I) optionally together with other active agents, particularly microbiocides or conservatives or the like.
  • Concentrated forms of compositions generally contain in between about 2 and 80%, preferably between about 5 and 70% by weight of active agent.
  • Application forms of formulation may for example contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations.
  • Tables 1.1 to 1.7 below illustrate the compounds of the invention.
  • the skilled person would understand that the compounds of formula (I) may exist as E and/or Z isomers as described herein before. Where mentioned the specific geometric configuration is not considered to be limiting.
  • Tables 1.2 to 1.7 discloses 61 individual compounds of the formula (I) in which A 1 , A 2 , X, Y, and R 1 are as specifically defined in Tables 1.2 to 1.7, which refer to Table 1 wherein R 2 is specifically defined.
  • Table 1
  • Table 1.2 This table discloses 61 specific compounds of the formula (I) wherein A 1 and A 2 are CH 2 , X is O, Y is CH, R 1 is methyl, and R 2 is as defined above in the Table 1.
  • Table 1.3 This table discloses 61 specific compounds of the formula (I) wherein A 1 and A 2 are CH 2 , X is O, Y is CH, R 1 is fluoro, and R 2 is as defined above in the Table 1.
  • Table 1.4 This table discloses 61 specific compounds of the formula (I) wherein A 1 is CH 2 , A 2 is CH 2 CH 2 , X is O, Y is CH, R 1 is hydrogen, and R 2 is as defined above in the Table 1.
  • Table 1.5 This table discloses 61 specific compounds of the formula (I) wherein A 1 and A 2 are CH 2 , X is O, Y is CH, R 1 is methoxy, and R 2 is as defined above in the Table 1.
  • Table 1.6 This table discloses 61 specific compounds of the formula (I) wherein A 1 and A 2 are CH 2 , X is O, Y is N, R 1 is hydrogen, and R 2 is as defined above in the Table 1.
  • Table 1.7 This table discloses 61 specific compounds of the formula (I) wherein A 1 and A 2 are CH 2 , X is NH, Y is N, R 1 is hydrogen, and R 2 is as defined above in the Table 1. EXAMPLES The Examples which follow serve to illustrate the invention.
  • the compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.
  • Compounds of formula (I) may possess any number of benefits including, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile (including improved crop tolerance), improved physico- chemical properties, or increased biodegradability).
  • LC/MS Liquid Chromatography Mass Spectrometry and the description of the apparatus and the methods is as follows: Method A: Spectra were recorded on a Mass Spectrometer from Waters Corporation (SQD, SQDII or QDA Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive and negative ions), Capillary: 0.8-3.00 kV, Cone: 5-30 V, Source Temperature: 120-150°C, Desolvation Temperature: 350-600°C, Cone Gas Flow: 50-150 l/h, Desolvation Gas Flow: 650-1000 l/h, Mass range: 50 to 900 Da and an Acquity UPLC from Waters Corporation: Binary pump, heated column compartment , diode-array detector and ELSD.
  • enantiomerically pure final compounds may be obtained from racemic materials as appropriate via standard physical separation techniques, such as reverse phase chiral chromatography, or through stereoselective synthetic techniques, eg, by using chiral starting materials.
  • Formulation Examples Wettable powders a) b) c) Active ingredient [compound of Formula (I)] 25 % 50 % 75 % sodium lignosulfonate 5 % 5 % - sodium lauryl sulfate 3 % - 5 % sodium diisobutylnaphthalenesulfonate - 6 % 10 % phenol polyethylene glycol ether - 2 % - (7-8 mol of ethylene oxide) highly dispersed silicic acid 5 % 10 % 10 % Kaolin 62 % 27 % - The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
  • Powders for dry seed treatment a) b) c) Active ingredient [compound of Formula (I)] 25 % 50 % 75 % light mineral oil 5 % 5 % 5 % highly dispersed silicic acid 5 % 5 % - Kaolin 65 % 40 % - Talcum - - 20 % The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
  • Emulsifiable concentrate active ingredient [compound of Formula (I)] 10 % octylphenol polyethylene glycol ether 3 % (4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate 3 % castor oil polyglycol ether (35 mol of ethylene oxide) 4 % Cyclohexanone 30 % xylene mixture 50 % Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.
  • Dusts a) b) c) Active ingredient [compound of Formula (I)] 5 % 6 % 4 % Talcum 95 % - - Kaolin - 94 % - mineral filler - - 96 % Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed. Extruder granules Active ingredient [compound of Formula (I)] 15 % sodium lignosulfonate 2 % Carboxymethylcellulose 1 % Kaolin 82 % The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.
  • Coated granules Active ingredient [compound of Formula (I)] 8 % polyethylene glycol (mol. wt.200) 3 % Kaolin 89 % The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.
  • Suspension concentrate Active ingredient [compound of Formula (I)] 40 % propylene glycol 10 % nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 % Sodium lignosulfonate 10 % Carboxymethylcellulose 1 % Silicone oil (in the form of a 75 % emulsion in water) 1 % Water 32 %
  • the finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • Active ingredient [compound of Formula (I)] 40 % propylene glycol 5 % copolymer butanol PO/EO 2 % tristyrenephenole with 10-20 moles EO 2 % 1,2-benzisothiazolin-3-one (in the form of a 20% solution in water) 0.5 % monoazo-pigment calcium salt 5 % Silicone oil (in the form of a 75 % emulsion in water) 0.2 % Water 45.3 % The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • Acetic acid (19.9 mL, 344 mmol, 2.00 equiv.) was then introduced dropwise at room temperature and the resulting suspension was stirred for 22 hours.
  • Triethyl amine (72.2 mL, 516 mmol, 3.00 equiv.) was then added dropwise while keeping the temperature constant with a water bath. The brown solution was stirred for 3 hours.
  • a mixture of saturated aqueous Na2S2O3 and saturated aqueous NaHCO 3 was then added, the layers were separated, and the aqueous layer was extracted with dichloromethane.
  • Step 2 Preparation of 8-bromo-N-ethoxy-tetralin-2-imine To a mixture of 8-bromotetralin-2-one (3.00 g, 13.3 mmol, 1.00 equiv.) in ethanol (20 mL) was added O- ethylhydroxylamine hydrochloride (4.02 g, 40.0 mmol, 3.00 equiv.) followed by sodium acetate (3.31 g, 40.0 mmol, 3.00 equiv.). The resulting reaction mixture was stirred at room temperature for 18 hours, then diluted with EtOAc and water, and extracted with EtOAc.
  • Step 3 Preparation of methyl N-ethoxy-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) tetralin-2-imine
  • 8-bromo-N-ethoxy-tetralin-2-imine (0.75 g, 2.80 mmol, 1.00 equiv.) in dioxane (5.60 mL) was added potassium acetate (0.55 g, 5.60 mmol, 2.00 equiv.) and bis(pinacolato)diboron (1.43 g, 5.60 mmol, 2.00 equiv.).
  • Step 4 Preparation of methyl (E)-2-(3-ethoxyiminotetralin-5-yl)-3-methoxy-prop-2-enoate
  • N-ethoxy-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tetralin-2-imine 400 mg, 1.27 mmol, 1.00 equiv.
  • dioxane 12.7 mL
  • water 0.63 mL
  • methyl (Z)-2-iodo-3-methoxy- prop-2-enoate 460 mg, 1.90 mmol, 1.50 equiv.
  • cesium carbonate (831 mg, 2.54 mmol, 2.00 equiv.) followed by addition of cataCXium-A-Pd-G3 (195 mg, 0.25 mmol, 0.20 equiv.).
  • Step 2 Preparation of methyl (E)-3-methoxy-2-(3-oxotetralin-5-yl)prop-2-enoate
  • 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tetralin-2-one (1.00 g, 3.67 mmol, 1.00 equiv.) in dioxane (36.7 mL) and water (1.84 mL) was added methyl (Z)-2-iodo-3-methoxy-prop-2- enoate (1.33 g, 5.51 mmol, 1.50 equiv.), cesium carbonate (2.41 g, 7.35 mmol, 2.00 equiv.), followed by cataCXium-A-Pd-G3 (563 mg, 0.73 mmol, 0.20 equiv.).
  • Step 3 Preparation of methyl (E)-3-methoxy-2-(3-prop-2-ynoxyiminotetralin-5-yl)prop-2-enoate
  • methanol 4.00 mL
  • O-prop-2-ynylhydroxylamine hydrochloride 100 mg, 0.92 mmol, 3.00 equiv.
  • sodium acetate 7.6.4 mg, 0.92 mmol, 3.00 equiv.
  • Example B Biological examples/test methods: Glomerella lagenarium syn. Colletotrichum lagenarium (anthracnose of cucurbits): Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24 °C and the inhibition of growth was determined photometrically after 72 hrs at 620nm.
  • the test plates were incubated at 24°C and the inhibition of growth was determined photometrically after approximately 5-6 days at 620nm.
  • the following compounds gave at least 80% control of Mycosphaerella arachidis at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: (Compounds of Table T1): 1.1, 1.2, 1.3, 1.4 Phakopsora pachyrhizi (Soybean rust): Soybean leaf disks are placed on agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf disks are inoculated with a spore suspension of the fungus.

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Abstract

L'invention concerne des composés de formule (I) dans laquelle les substituants sont tels que définis dans la revendication 1, sont utiles en tant que pesticides, en particulier en tant que fongicides.
PCT/EP2021/075770 2020-09-21 2021-09-20 Composés microbiocides WO2022058580A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116410184A (zh) * 2023-04-07 2023-07-11 西南大学 喹唑酮烯酮唑类化合物及其制备方法和应用

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