WO2000041999A1 - Derives d'oxime et utilisations associees - Google Patents

Derives d'oxime et utilisations associees Download PDF

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Publication number
WO2000041999A1
WO2000041999A1 PCT/JP2000/000060 JP0000060W WO0041999A1 WO 2000041999 A1 WO2000041999 A1 WO 2000041999A1 JP 0000060 W JP0000060 W JP 0000060W WO 0041999 A1 WO0041999 A1 WO 0041999A1
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group
optionally substituted
methyl
general formula
compound
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PCT/JP2000/000060
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English (en)
Japanese (ja)
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Yoshiharu Kinoshita
Hiroshi Sakaguchi
Akio Manabe
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Sumitomo Chemical Company, Limited
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Priority to AU18922/00A priority Critical patent/AU1892200A/en
Publication of WO2000041999A1 publication Critical patent/WO2000041999A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • 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
    • C07C251/36—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C251/40—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te

Definitions

  • the present invention relates to oxime derivatives and uses thereof.
  • An object of the present invention is to provide a compound having excellent plant disease controlling effect and insecticidal and acaricidal effect.
  • the present inventors have found that the oxime derivative represented by the following general formula [1] has excellent plant disease controlling and insecticidal and acaricidal effects, and have completed the present invention. .
  • a 1 , A 2 and A 3 are the same or different and are each a hydrogen atom, an optionally substituted C 1 -C 10 alkyl group, an optionally substituted C 2 -C 10 alkenyl group, substituted Optionally substituted C2-C10 alkynyl group, optionally substituted C3-C10 cycloalkyl group, optionally substituted C5-C10 cycloalkenyl group, substituted C 6 or C 10 aryl group, optionally substituted C 7 -C 19 arylalkyl group, optionally substituted C 1 -C 9 heteroaryl group, optionally substituted
  • U and V represents a CR 2 group, the other represents a CH group or a nitrogen atom, and W represents a CR 3 group or a nitrogen atom.
  • R 2 and R 3 are the same or different, and are a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkyl group, a C1-C6 It represents a haloalkoxy group, a cyano group, a nitro group, a C2-C6 alkoxycarbonyl group, a C1-C6 alkylthio group or a C1-C6 haloalkynolethio group.
  • ⁇
  • Y represents an oxygen atom or a NH group.
  • Examples of the C 1 -C 10 alkyl group in the optionally substituted C 1 -C 10 alkyl group represented by RAA 2 and A 3 include a methyl group, an ethyl group, a propyl group, an isopropyl group and a butyl group.
  • Isobutyl 1-methylpropyl, pentyl, 1-methylbutyl, 1-ethylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl group, hexyl group, 1-methylpentyl group, 1-ethylpentyl group, 3,3-dimethylbutyl group, heptyl group, 3,7-dimethylo group Butyl group and the like,
  • Examples of the C 5 to C 10 cycloalkenyl group in the optionally substituted C 5 to C 10 cycloalkenyl group represented by R ⁇ A 1 , A 2 and A 3 include, for example, cyclopentenyl group, cyclohexenyl group Groups, etc.,
  • Examples of the C 6 or C 10 aryl group in the optionally substituted C 6 or C 10 aryl group represented by RAA 2 and A 3 include a phenyl group, a hinaphthyl group and a / 3-naphthyl group.
  • Examples of the C 1 -C 9 heteroaryl group in the optionally substituted C 1 -C 9 heteroaryl group represented by R 1 A 1 , A 2 and A 3 include, for example, a 2-pyridyl group, a 3-pyridyl group, 4-monopyridyl, 2-pyrimidinyl, 4-pyrimidinyl,
  • 2-pyrazul 2-chenyl, 3-chenyl, 2-furyl, 3-furyl, pyrrole-1-yl, 1-pyrazolyl, 3-pyrazolyl, 4-virazolyl, 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group, 2-oxoazolyl group, 5-oxazolyl group, 2-imidazolyl group, 3- (1,2,4-triazolyl) group, 2-benzozoenyl Group, 3-benzochel group, benzothiazoyl 2-yl group, 2-quinolinyl group and the like.
  • Examples of the C 2 -C 10 alkenyl group in the optionally substituted C 2 -C 10 alkenyl group represented by AA 2 and A 3 include, for example, a bier group, an aryl group, a 1-methyl-2-propenyl group , 2-methyl-2-propenyl group, 2-butenyl group, 2-pentenyl group, 3-methyl-2-butenyl group and the like,
  • a C 2 to C 10 alkynyl groups in the optionally substituted C 2 to C 10 alkynyl groups represented by AA 2 and A 3 include an ethynyl group, a 1-propynyl group,
  • the optionally substituted C 1 -C 9 trialkylsilyl group represented by A 1 , A 2 and A 3 which may be substituted may be a trimethylsilyl group, a triethylsilyl group, Ethylmethyl propylsilyl group, etc.
  • the optionally substituted C 8 to C 15 dialkylaryl silyl group represented by AA 2 and A 3 may be substituted as a C 8 to C 15 dialkylaryl silyl group, such as a dimethylphenylsilyl group, Ethylmethylphenylsilyl group, getylfurylsilyl group, etc.
  • the optionally substituted C 3 -C 20 dialkylaryl silyl group represented by AA 2 and A 3 which may be substituted may be an ethoxydimethylsilyl group, getylmethyl. And a toxicsilyl group.
  • examples of the C 6 or C 10 aryl group in the optionally substituted C 6 or C 10 aryl group represented by A 4 include a phenyl group, an ⁇ -naphthyl group and a ⁇ -naphthyl group,
  • C 1 through C 9 optionally Heteroariru group
  • C 1 through C 9 Heteroari Ichiru group represented by Alpha 4 for example 2-pyridyl, 3-pyridyl, 4 one pyridyl group, 2-pyrimidinyl Group, 4-Pirimigel group, 2-Viladinyl group, 2-Chenyl group, 3-Chenole group, 2-Fryl group, 3-Frinole group, Pyroyl-1-ynole group, 1-Vilazolyl group, 3-Vilazolyl Group, 4-birazolyl group, 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group, 2-oxazolyl group, 5-oxazolyl group, 2-imidazolyl group, 3- (1,2,4-triazolyl) group , 2-benzobenzoinole, 3-benzobenzoinole, benzothiazonole 2- ⁇ nore, 2-quinolinyl and the like.
  • R 1 , AA 2 and optionally substituted C 3 to C 10 cycloa represented by A 3 Alkyl group, an optionally substituted C5-C1 cycloalkenyl group, an optionally substituted C6 group may be a C10 aryl group, an optionally substituted C1-C9 heteroaryl group, A 1, A 2 and A 3 substituted by C 2 to C 1 optionally 0 alkenyl group represented, optionally substituted C 2 to C 10 alkynyl groups, optionally substituted C 7 ⁇ C 19 arylalkyl group, optionally substituted C2-C19 heteroarylalkyl group, optionally substituted C1-C9 trialkylsilyl group, optionally substituted C8-C
  • substituent in the 15 dialkylarylsilyl group include, for example,
  • Halogen atom (chlorine atom, bromine atom, fluorine atom, iodine atom),
  • C1-C10 alkyl group [for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, 1-methylpropyl group, pentyl group, 1-methylbutyl group, 1-ethylinobutyl group, 2-methylinobutynole Group, 3-methylinobutyl group, 2,2-dimethylpropyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, hexyl group, 1-methylpentyl group, 1-ethylpentyl group, 3,3-dimethylbutyl group, Heptyl group, 3,7-dimethyloctyl group, etc.),
  • a C1-C10 haloalkyl group [eg, trifluoromethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, etc.],
  • C3-C10 cycloanoalkyl group for example, cyclopropyl group, cyclopentyl group, cyclohexyl group, etc.
  • C1-C10 alkoxy groups for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, n-pentyloxy, etc.
  • C 1 -C 10 haloalkoxy group for example, trifluoromethoxy group, difluoromethoxy group, bromodifluoromethoxy group, chlorodifluoromethoxy group, fluoromethoxy group, 2,2,2-trifluoromethoxy group, 1,1,2,2-tetrafluoroethoxy group etc.
  • C1-C10 alkylthio group [for example, methylthio group, ethylthio group, n-propylthio group, n-butylthio group, isobutylthio group, sec-butylthio group, n-pentylthio group, n-hexylthio group, etc.],
  • C1-C10 haloalkylthio group [for example, trifluoromethylthio group, difluoromethylthio group, bromodifluoromethylthio group, chlorodifluoromethylthio group, fluoromethylthio group, 2,2,2-trihno Leoloethylthio group, 1,1,2,2-tetrafluoroethylthio group, etc.],
  • C2-C10 alkoxycarbonyl group [methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, isobutoxycanolebonyl group, sec-butoxycarbonyl group, n —Pentyloxycarbonyl group, n-hexyloxycarbol group, etc.), C 2 -C 10 alkylcarbonyl group (acetyl group, propanoyl group, butanol group, etc.),
  • C2-C10 alkylcarbonylamino group (acetylamino group, propanoylamino group, butanoylamino group, etc.),
  • a group, a heteroaryl group, a heteroaryloxy group, a heteroarylmethyleneoxy group and a heteroaryloxymethylene group are a nitrogen atom (for example, a chlorine atom), a C1-C6 alkyl group (for example, A methyl group, an ethyl group, etc., a C1-C6 alkoxy group (e.g., a methoxy group, an ethoxy group, etc.), a C1-C6 haloalkyl group (e.g., a trifluoromethyl group, etc.), C:!-C6 halo An alkoxy group (eg, trifluoromethoxy group
  • C3-C20 dialkylalkoxysilyl group (dimethylethoxysilyl group, ethylmethylethoxysilyl group, dimethylbutoxysilyl group, etc.),
  • a C7-C20 alkyldicycloalkoxysilyl group [di (cyclohexyloxy) methylsilyl group, di (cyclohexyloxy) ethylsilyl group, etc.], a hydroxyl group, a cyano group, and a nitro group.
  • Examples of the halogen atom represented by R 2 and R 3 include a chlorine atom and a bromine atom.
  • Examples of the C 1 -C 6 alkyl group represented by R 2 and R 3 include a methyl group and an ethyl group.
  • alkoxy group for example main butoxy group represented by R 2 and R 3, E butoxy group and the like,
  • Examples of the C 1 -C 6 haloalkoxy group represented by R 2 and R 3 include trifluoromethoxy, difluoromethoxy, bromodifluoromethoxy, chlorodifluoromethoxy, fluoromethoxy, 2,2,2- Trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group and the like.
  • C 2 to C 6 alkoxycarbonyl as the group for example main preparative alkoxycarbonyl group represented by R 2 and R 3, E-butoxycarbonyl group and the like,
  • C 1 through C 6 for example a methylthio group as the alkylthio group represented by R 2 and R 3, Echiruchio group and the like
  • Examples of the C 1 -C 6 haloalkylthio groups represented by R 2 and R 3 include trifluoromethylthio, difluoromethylthio, bromodifluoromethylthio, chlorodifluoromethylthio, fluoromethylthio, and 2 , 2,2-trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, and the like.
  • 6-membered aromatic ring containing U, V and W include a benzene ring, a pyridine ring, a pyrimidine ring and the like.
  • the terms (E) and (Z) used herein are defined by the force-in-gold-prelog rule widely used to indicate geometric isomers.)
  • preferred substituents in terms of the plant disease controlling effect include, as R 1 , an optionally substituted phenyl group and an A 1 -C 3 C single group.
  • the 6-membered aromatic ring moiety containing U, V and W which is preferable in view of the plant disease controlling effect
  • a ring wherein U, V and W are all CH groups can be mentioned.
  • examples of more preferable compounds in terms of the efficacy of controlling plant diseases include N-methyl-13- (2-methynole-15-pheninole) phenyl-12- (methoxyimino) propanamide [book Invention compound 1]
  • preferred substituents in terms of insecticidal and acaricidal efficacy include A 1 -C 3 C- as R 1 .
  • the 6-membered aromatic ring moiety containing U, V and W which is preferable in terms of insecticidal and acaricidal efficacy, includes a ring in which U, V and W are all CH groups.
  • examples of more preferred compounds in terms of insecticidal and acaricidal efficacy include a ring in which U, V and W are all CH groups.
  • the compound of the present invention can be produced, for example, according to the following Production Methods A to J.
  • a protecting group can be used if necessary to protect the functional group from the reaction.
  • Production method A A method for producing an oxime ester represented by the general formula [11], wherein Y is an oxygen atom in the general formula [1].
  • the oxime ester represented by the general formula [111] can be produced, for example, from the compound represented by the general formula [I] by a method shown in scheme (1).
  • DIBAL diisobutylaluminum hydride
  • Me represents a methyl group
  • Ac represents an acetyl group.
  • the aldehyde compound represented by the general formula [ ⁇ ] can be produced by reducing the nitrile conjugate represented by the general formula [I] using, for example, diisobutylaluminum hydride.
  • the azalactone compound represented by the general formula [II] is produced by reacting the aldehyde compound represented by the general formula [II] with N-acetylglycine in the presence of acetic anhydride and sodium acetate. can do.
  • the reaction temperature of the reaction is usually in the range of 100 to 200 ° C, and the reaction time is usually in the range of 1 to 100 hours.
  • the amount of the reagent used in the reaction is usually 1 to 10 mol of N-acetylglycine and 1 to 1 mol of sodium acetate to 1 mol of the aldehyde compound represented by the general formula [ ⁇ ].
  • the acetic anhydride is usually in a proportion of 1 to 100 mol, in a proportion of 0 mol.
  • reaction solution After the reaction is completed, for example, excess acetic anhydride in the reaction solution is distilled off, and the residue is subjected to chromatography, or the reaction solution is poured into water, followed by post-treatment such as extraction with an organic solvent and concentration.
  • the desired compound can be obtained.
  • the compound can be purified by recrystallization, chromatography or the like.
  • the amide compound represented by the general formula [IV] can be produced by reacting the azalactone represented by the general formula [III] with methanol in the presence of an aqueous sodium hydroxide solution.
  • the reaction temperature of the reaction is usually in the range of 20 to 80 ° C, and the reaction time is usually in the range of 1 to 100 hours.
  • the amount of the reagent used for the reaction is usually 1 to 100 mol of methanol to 1 mol of the azalactone represented by the general formula [III], and the aqueous sodium hydroxide solution is usually 0.0 to 1 mol. 0 It is a ratio of 1 to 1 mol.
  • reaction solution After completion of the reaction, the reaction solution can be partially concentrated and then subjected to a post-treatment such as extraction with an organic solvent to obtain a target compound.
  • a post-treatment such as extraction with an organic solvent to obtain a target compound.
  • the compound can be purified by recrystallization, chromatography or the like.
  • the oxime ester aldehyde compound represented by the general formula [111] can be produced by reacting the amide compound represented by the general formula [IV] with methoxamine in the presence of an acid. .
  • the reaction temperature of the reaction is usually in the range of 0 to 50 ° C, and the reaction time is usually 1 to 100 ° C. Time range.
  • the amount of the reagent used in the reaction is usually 1 to 20 moles per 1 mole of the amide compound represented by the general formula [IV], and the acid is usually 0.1 to 3 moles per mole of the amide compound represented by the general formula [IV]. Ratio.
  • Methoxyamine can be used as it is or as a salt such as hydrochloride or sulfate.
  • the acid examples include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as oxalic acid and p-toluenesulfonic acid.
  • the reaction is usually carried out using a solvent.
  • a solvent examples include alcohols such as methanol and ethanol, aliphatic hydrocarbons such as n-hexane, n-heptane, lignin, petroleum utel, and toluene. And aromatic hydrocarbons such as xylene, water, etc., and mixtures thereof.
  • the compound After completion of the reaction, for example, after pouring the reaction solution into water, post-treatments such as extraction with an organic solvent and concentration are performed to obtain a target compound.
  • the compound can be purified by recrystallization, chromatography or the like.
  • the diamide compound represented by the general formula [V] is an azalactone represented by the general formula [ ⁇ ⁇ ] And methylamine.
  • the reaction temperature of the reaction is usually in the range of 0.50 ° C., and the reaction time is usually in the range of 110 hours.
  • the amount of the reagent used for the reaction is usually 1100 mol of methylamine to 1 mol of the azalactone compound represented by the general formula [ ⁇ ].
  • the reaction is usually carried out using a solvent.
  • a solvent examples include 1,4-dioxane, tetrahydrofuran, ethyleneglycol dimethinoleate ⁇ ethylene glycol-one-resin-methinoleate-note, tert-butylene-note-note, tert-butylinone-note-no-note Aliphatic hydrocarbons such as n-xane, n-heptane, lignin, petroleum ether, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol and ethanol , Water and the like or a mixture thereof.
  • the crystals formed in the reaction solution are filtered, and the crystals are dried, or the reaction solution is poured into water, and then subjected to a post-treatment such as extraction with an organic solvent, concentration, and the like. Can be obtained.
  • the compound can be purified by recrystallization, chromatography or the like.
  • the oxime amide compound represented by the general formula [112] can be produced by reacting the amide compound represented by the general formula [V] with methoxamine in the presence of an acid.
  • the reaction temperature of the reaction is usually in the range of 210 ° C., and the reaction time is usually in the range of 110 hours.
  • the amounts of the reagents used in the reaction are such that methoxyamine is usually used in a ratio of 120 mol and acid is usually used in a ratio of 0.13 mol per 1 mol of the diamide compound represented by the general formula [V]. is there.
  • Methoxyamine can be used as it is or as a salt such as hydrochloride or sulfate.
  • the acid examples include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as oxalic acid and p-toluenesulfonic acid.
  • the reaction is usually performed using a solvent.
  • solvents include, for example, methanol Alcohols such as toluene, ethanol, etc., aliphatic hydrocarbons such as n-hexane, n-heptane, lignin, petroleum ether, aromatic hydrocarbons such as toluene and xylene, water, and mixtures thereof.
  • methanol Alcohols such as toluene, ethanol, etc.
  • aliphatic hydrocarbons such as n-hexane, n-heptane, lignin, petroleum ether, aromatic hydrocarbons such as toluene and xylene, water, and mixtures thereof.
  • the compound After completion of the reaction, for example, after pouring the reaction solution into water, post-treatments such as extraction with an organic solvent and concentration are performed to obtain a target compound.
  • the compound can be purified by recrystallization, chromatography or the like.
  • the reaction temperature of the reaction is usually in the range of 110 to 50 ° C, and the reaction time is usually in the range of 1 to 100 hours.
  • the amount of the reagent used in the reaction is usually 1 to 100 mol of methylamine per 1 mol of the oxime ester represented by the general formula [1-1].
  • examples of such a solvent include 1,4-dioxane, tetrahydrofuran, ethylene glycolone resin / leate, diethylene glycol dimethyl ether, ethynol ether, tert-butynolemethyl Ethers such as ether, aliphatic hydrocarbons such as n-hexane, n-heptane, lignin, petroleum ether, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol and ethanol; Water and the like or a mixture thereof are mentioned.
  • a post-treatment such as concentration of the reaction solution is performed to obtain a target compound.
  • the compound can be purified by recrystallization, chromatography and the like.
  • R 1 is an optionally substituted C 6 or C 10 aryl group or an optionally substituted C 1 to C 9 heteroaryl group.
  • R 11 represents an optionally substituted C 6 or C 10 aryl group or an optionally substituted C 1 C 9 heteroaryl group
  • Z represents a halogen atom (chlorine, bromine, iodine).
  • X represents a bromine atom, an iodine atom or a trifluoromethanesulfonyloxy group
  • YUV and W have the same meanings as described above.
  • the borate compound represented by the general formula [114] can be obtained by mixing a halide represented by the general formula [113] with bis (pinacolato) diborane in an organic solvent (dimethyl sulfoxide, dimethylformamide, etc.). ), A base (potassium acetate, potassium carbonate, etc.) and a palladium catalyst (dichloromethane complex of [bis (diphenylphosphino) phenethyl] dichloropalladium (II), tetrakistriphenylphosphine palladium, etc.)
  • the reaction can be carried out (more specifically, for example, according to the method described in J. Org. Chem., 1995 60 7508-7510.).
  • the reaction solution is poured into water and then subjected to post-treatments such as extraction with an organic solvent and concentration to obtain a target compound.
  • the compound can be purified by recrystallization or the like.
  • the oxime compound represented by the general formula [11] is a compound represented by the general formula [1_4].
  • reaction solution can be subjected to post-treatments such as, for example, distilling off the solvent and then subjecting the residue to chromatography or extracting with an organic solvent and concentrating to obtain a target compound.
  • post-treatments such as, for example, distilling off the solvent and then subjecting the residue to chromatography or extracting with an organic solvent and concentrating to obtain a target compound.
  • the compound can be purified by recrystallization, chromatography or the like.
  • X 1 represents a bromine atom or an iodine atom, and A 1 U, V and the same meaning as described above. ]
  • the reaction is carried out, for example, in a nonprotonic polar solvent (acetonitrile, N, N-dimethylformamide, etc.), a base (secondary amine such as diisopropylamine, tertiary amine such as triethylamine) and a catalyst (bis (trifamine).
  • a nonprotonic polar solvent acetonitrile, N, N-dimethylformamide, etc.
  • a base secondary amine such as diisopropylamine, tertiary amine such as triethylamine
  • a catalyst bis (trifamine).
  • PdCl 2 (PPh 3 ) 2 a combination of copper (I) iodide and trifuunylphosphine
  • the reaction is for example, a mixed solvent of water and dimethyl Tokishetan, bases (inorganic bases such as sodium bicarbonate) and a catalyst (tetrakis (Torifuweniru) palladium ⁇ hereinafter abbreviated as P d (PP h 3) 4 ⁇ and the like) (More specifically, for example, according to the method described in Beispie 12 of International Patent Application No. WO 96/35669, published in WO 96/35669).
  • a base such as an inorganic base such as potassium carbonate
  • a catalyst such as palladium acetate
  • reaction solution is subjected to post-treatments such as extraction with an organic solvent and concentration to obtain a target compound.
  • the compound can be purified by recrystallization, chromatography and the like.
  • a 4 represents an optionally substituted C 6 or C 10 aryl group or an optionally substituted C 1 -C 9 heteroaryl group
  • U, V, W, X 1 and Y Represents the same meaning as described above.
  • the reaction is carried out, for example, in an organic solvent (such as methylene chloride) in the presence of a base (such as an organic base such as triethylamine, an inorganic base such as baking soda) and a catalyst (such as copper acetate (II)).
  • a base such as an organic base such as triethylamine, an inorganic base such as baking soda
  • a catalyst such as copper acetate (II)
  • the reaction is carried out, for example, using a base (an organic base such as triethylamine, an inorganic base such as potassium carbonate or cesium carbonate) and a catalyst (eg, copper (I) iodide) in an organic solvent (such as toluene and ethyl acetate).
  • a base an organic base such as triethylamine, an inorganic base such as potassium carbonate or cesium carbonate
  • a catalyst eg, copper (I) iodide
  • organic solvent such as toluene and ethyl acetate
  • a 11 has the same meaning as A 1 except for a hydrogen atom, and L represents a chlorine atom, a bromine atom, an iodine atom, a p-toluenesulfonyloxy group, a methanesulfo-loxy group, a trifluoromethanesulfonyloxy group.
  • a 2 , U, V, W and Y have the same meaning as described above.
  • AA 2 , L, U, V, W and Y represent the same meaning as described above.
  • the compound of the present invention when used as an active ingredient in agricultural and horticultural fungicides, it may be used as it is without adding any other components, but it is usually used for solid carriers, liquid carriers, surfactants, and other pharmaceutical preparations. It is mixed with adjuvants and formulated into emulsions, wettable powders, wettable granules, emulsion preparations, flowables, powders, granules and the like. These preparations usually contain the compound of the present invention as an active ingredient in an amount of 0.1 to 90% based on the total preparation weight.
  • Examples of the solid carrier used in the preparation include minerals such as kaolin clay, attapuljay clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder, Fine powder or granules composed of natural organic substances such as husk powder, synthetic organic substances such as urea, salts such as calcium carbonate and ammonium sulfate, and synthetic inorganic substances such as synthetic hydrous silicon oxide.
  • minerals such as kaolin clay, attapuljay clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder, Fine powder or granules composed of natural organic substances such as husk powder, synthetic organic substances such as urea, salts such as calcium carbonate and ammonium sulfate, and synthetic inorganic substances such as synthetic hydrous silicon oxide.
  • liquid carrier examples include aromatic hydrocarbons such as xylene, alkylbenzene, and methylnaphthalene; alcohols such as isopropanol, ethylene glycol, propylene glycol, and cellosolve; acetone, cyclohexanone, and isophorone.
  • aromatic hydrocarbons such as xylene, alkylbenzene, and methylnaphthalene
  • alcohols such as isopropanol, ethylene glycol, propylene glycol, and cellosolve
  • acetone, cyclohexanone, and isophorone examples include olive oils such as soybean oil and cottonseed oil, petroleum aliphatic hydrocarbons, esters, dimethyl sulfoxide, acetonitrile, water and the like.
  • Surfactants include, for example, alkyl sulfates, alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphates, lignin snolenate, and naphthalene sulfonate formalin condensation
  • nonionic surfactants such as polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl polyoxypropylene block copolymer, and sorbitan fatty acid ester.
  • Pharmaceutical adjuvants include, for example, water-soluble polymers such as polyvinyl alcohol and polyvinylpyrrolidone, gum arabic, alginic acid and its salts, polysaccharides such as CMC (carboxymethylcellulose), xanthan gum, etc., aluminum magnesium silicate, alumina sol, etc.
  • the application method of the compound of the present invention include foliage application, soil treatment, seed disinfection, and the like, and further, it can be used in any application method usually used by those skilled in the art.
  • the application rate of the active ingredient depends on the type of the target plant (crop, etc.), the type of the target disease, the degree of occurrence of the disease, the formulation, the application method, and the application. time may vary depending weather conditions, etc., per 1 are normally 0. 0 1 to 5 0 g, preferably 0. 0 5 to 1 0 8 Dearu.
  • the application concentration is 0.0000 :! 33%, preferably 0.001% to 1%, and dusts, granules and the like are applied without any dilution.
  • the compound of the present invention can be used as a fungicide for agricultural and horticultural use in fields, paddy fields, orchards, tea fields, pastures, turf, etc., and is used in combination with or used in combination with other agricultural and horticultural fungicides. This can be expected to increase the bactericidal efficacy.
  • Other fungicides for agricultural and horticultural use that can be used in combination or in combination are, for example, propiconazole, triadimenol, pu chloraz, penconazo monole, tef, 'conazo monole, funoresilazole, diniconazole, bromconazo one.
  • Plant diseases that can be controlled by the compound of the present invention include, for example, the following diseases.
  • Wheat powdery mildew (Erysiphe graminis), red blight (Gibberel la zeae), ⁇ ⁇ (Puccinia stri iformis, P. graminis, P. recondita, P. hordei), snow rot (Typhula sp., Micronectriel la nival is) naked smut (Usti lago tri tici, U.
  • Apple moyuria disease (Sclerotinia mali), rot (Valsa mali), powdery mildew (Podosphaera leucotricha), N spotted spotted leaves (Alternaria mali), scab (Vent uria inaequalis)
  • Eggplant blotch disease (Phomopsis vexans), Tsutonko hei (Erysiphe cichoracearum), Cruciferous vegetable black spot (Alternaria japonica), Vitiligo ⁇ hei (Cercosporella bras sicae),
  • Green onion rust (Puccinia allii), soybean purpura (Cercospora kikuchii), black rot (Elsinoe glycines), sunspot (Diaporthe phaseolorum var. Soja e), kidney bean cole (Colletotrichum linderathianum), black laccase Mildew (Cercospora personate), Brown spot (Cercospora arachidicola), Endo powdery mildew (Erysiphe pisi), Summer blight of potatoes (Alternaria solani), Phytophthora (Phytophthora infestans), Strawberry sponge (Sphaero) ) Exobasidium reticulatum, White scab (El sinoe leucospi la), Tano, Koboshi (Al ternaria longipes), Tsudonko (Erys iphe cichoracearu m Anthracnose (Col letotri chum tabacum)) When;
  • the compound of the present invention When used as an active ingredient of insecticides and acaricides, it may be used as it is without adding any other components, but usually, a solid carrier, a liquid carrier, a gaseous carrier, a bait, etc. And, if necessary, adding a surfactant and other formulation auxiliaries, and adding oily IJ, emulsions, wettable powders, flowables, microcapsules, granules, powders, and azoles. , Aerosols (fogging, etc.), poison bait etc. are used as a formulation. These preparations usually contain the compound of the present invention as an active ingredient in an amount of 0.01% to 95% based on the total weight of the preparation.
  • Examples of the solid carrier used in the formulation of kalu are, for example, clays (such as Oriental clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, fubasami clay, acid clay), talcs, ceramics, and other inorganic minerals ( Fine powders or granular materials such as sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica, etc., and chemical fertilizers (ammonium sulfate, phosphorous ammonium, ammonium nitrate, urine, salt ammonium, etc.).
  • clays such as Oriental clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, fubasami clay, acid clay
  • talcs such as sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica, etc.
  • chemical fertilizers ammonium sulfate, phosphorous ammonium, ammonium nitrate, urine, salt ammonium, etc.
  • surfactant examples include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl esters and polyoxyethylenates thereof, polyethylene glycol ethers, polyhydric alcohol esters, and the like. And sugar alcohol derivatives.
  • Examples of pharmaceutical adjuvants such as fixatives and dispersants include casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (Polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.).
  • Stabilizers include, for example, PAP (isopropyl oxyphosphate), BHT (2,6-di-tert-butynole 4-methyl / refpheno).
  • BHA a mixture of 2-tert-butynole 4-methoxyphenol and 3-tert-butyl-14-methoxyphenol
  • vegetable oils mineral oils
  • surfactants fatty acids or their esters, etc. Is raised.
  • Base materials for the bait include, for example, feed components such as cereal flour, vegetable oil, sugar, and crystalline cellulose; Examples include an ingestion inhibitor such as pepper powder, an attractive flavor such as a cheese flavor, and an onion flavor.
  • the application rate of the active ingredient is usually from 0.1 g to 100 g per 10 ares.
  • the application concentration is usually 0.1 lpm ⁇ :! O O O O ppm, granules, powders, etc. are applied as is without dilution.
  • insecticide for mitigating insects, emulsions, wettable powders, flowables, microcapsules, etc. are usually diluted with water to 0.1 ppm to 5000 ppm and applied to oils.
  • aerosols, aerosols, poison baits, etc. apply as is.
  • application rates and application concentrations can vary depending on the type of preparation, application time, application place, application method, type of pest, degree of damage, etc., but may be increased or decreased without being affected by the above range be able to.
  • the compound of the present invention can be mixed or used in combination with other insecticides, nematicides, and acaricides.
  • strong insecticides and Z or acaricides and Z or nematicides include, for example, phennitrothion, fenthion, diazinon, chlorpyrifos, acephate, methidathion, disunolephoton, DDVP, su / reprophos, cyanophos, prophenofos, dime Organophosphorus compounds such as frequency, fenthate, malathion, triclonolefon, azinphosmethine, etc.
  • Carbamate compounds such as aldicarp, oxamil, phenothiocalp, and thiodicarp, etofenprox, fenvalerate, esfenvalerate, fenprono, ° trin, cypermet Phyloresin such as phosphorus, alpha cypermethrin, zetacypermethrin, permethrin, sinoprotrine, lambda cyhalothrin, deletametrin, tralomethrin, cycloprothrin, taufulvalinate, bifenthrin, aclinatrin, halfenprox, silafludompri, etc.
  • cypermet Phyloresin such as phosphorus, alpha cypermethrin, zetacypermethrin, permethrin, sinoprotrine, lambda cyhalothrin, deletametrin, tralome
  • Thiamethoxam, neonicotinoid compounds such as ditenviram, neura toxin derivatives such as cartap, thiocyclam, and vensultap, endosnolephane, gamma-BHC, 1,1-bis (clo-phenyl) 1,2,2,2 Chlorinated hydrocarbons such as trichloroethanol, chlorfluazuron, tefluvenzuron, flufenoxuron, diph / levensuron, hexaf / remulon, norefeni Benzoylphenylperrea compounds such as benzoylphenyl, formamide derivatives such as amitraz and chlordimeform, phenylvirazole compounds, phenylhydrazine derivatives such as halofenozide, methoxyphenozide, chlorphenavir, bromopropiryl Tetradifone, propargite, fenbutatin oxide, hexit
  • Hemiptera Hime Tobiunka (Laodelphax striatel lus), Tobiirounka (Ni l aparvata lugens), Unka such as Sejirounka (Sogatel la furcif era), Tsumagu Royokono I (Nephotettix cincticeps; lambda Chiyanomi Dorihimeyokono I (Empoasca on ukii) etc.
  • Aphids such as leafhoppers, Aphis gossypi i and Aphid aphids (Myzus persicae), stink bugs, Trifoliate lice (Trialeu rodes vaporariorum ⁇ ⁇ ); ⁇ i Nashif (Bemisia taoaci), Leaf r Whiteflies such as white lice (Bemisia argentifol ii), scale insects, dwarf bugs, white lice, etc.
  • Lepidopteran pests Chilo suppressal is, Cnaphalocroci s medinal is, Ostrinia nubi lal is, maggots such as Parapediasia teterrel la, etc .; ⁇ (Spodoptera l itur a) N Shiroichimosho h '(Spodoptera exigua), down' ® Bokuu (Pseudaletia separa ta), ® Bok ⁇ moth (Mamestra brassicae), black cutworm (Agroti s ipsi lon), Bok Rikopu Noreshia genus (Trichopl 'usia spp.), Heliotis spp., Helicoverpa spp., Aerias (Earias spp.), etc., and Pieris rapae crucivora ), Etc., Ado xophyes orana fasciata, Nashihimesingu (Grapno
  • Peach moth moth moth moth moth (Lyonetia clerkel la), etc .; homo moth moth moth (Phyl lonorycter ringoniel la); moth moth moth moth (Phyl locnistis citrel la); moth moth moth (Plutela xylostella); Ball worms (Pectinophora gossypiel la), etc., Kigaga, Higatoga, Hirozuga, etc.
  • Diptera pests, houseflies, anopheles, mosses, house flies, houseflies, blowflies, flies, flies, flies, flies, flies, and flies , Buchus, flies, etc.
  • Coleopteran pests beetles, chafers, weevils, carabidae, ladybirds Bugs, Longicorn beetles, Tenebrion beetles, etc.
  • Thrips of the order Thrips palmi Thrips genus such as Thrips palmi, genus Frankliniella such as Frankliniella occidental is, and silt slips such as Sci ltothrips dorsal is Thrips of the genus, etc.
  • Hymenoptera pests wasps, squirrels, hornets, etc.
  • Orthoptera pests Grasshoppers, Kera, etc.
  • Laminariat pests flea flea, etc.
  • Termite pests termites, etc.
  • Production Examples of the compound of the present invention and Production Examples of intermediates for producing the compound of the present invention are shown in Production Examples and Reference Production Examples.
  • the numbers of the compounds of the present invention are the compound numbers described in Tables 1 to 22 below.
  • Production Example 1 Production method of compound 40 of the present invention represented by formula [2]
  • N-Methyl-1-acetylamide 3- (5-bromo_2-methylphenyl) -acrylamide (compound represented by the formula [6]) 1.86 g (6. Ommo 1) and 551 mg of methoxamine hydrochloride To a solution of (6.6 mmol) in a mixed solvent of methanol (28 ml) and water (1 ml), concentrated hydrochloric acid (0.7 ml) was added. After stirring at the reflux temperature for 22 hours, the solvent was distilled off under reduced pressure, and the residue was diluted with chloroform.
  • Na-type X zeolite dry powder (Zeolam typeF-9, manufactured by Tosoichi Co., Ltd .; 100 mesh or less) While stirring 100 g, 2-methylbenzonitrile 17.6 g (15 Ommo 1) was added dropwise. There, 45-50. 32.0 g (20 Ommo 1) of bromine was added dropwise at C, and the mixture was stirred at 80 ° C for 2 hours. Methanol (200 ml) was added, the mixture was stirred at room temperature for 1 hour, and then filtered. The remaining zeolite powder was further washed with methanol (100 ml ⁇ 4 times). The filtrate and washings were combined and concentrated.
  • Equation [4] Under a nitrogen atmosphere, a solution of 5.58 g (3 Ommo 1) of 5-bromo-2-methylbenzonitrile in 30 ml of toluene at ⁇ 30 ° C. in toluene solution of diisobutylaluminum hydride (1 .5M solution) 24 ml (36 mmo)) was added dropwise. The mixture was stirred for 5 hours while gradually raising the temperature to 0 DC . After diluting hydrochloric acid in an ice bath to make the solution neutral, methanol and celite were added, and the mixture was stirred for 1 hour, and then filtered to remove insolubles.
  • N-Methyl-1- (5-bromo-2-methylphenol) -12- (Methoxyimino) propanamide 1 20 mg (0.40 mmo 1), 2-Methynolepheninoleboronate 68 m g (0.5 Ommo 1), tetra bromide_n-butylammonium 12.9 mg (0.4 Ommo 1), potassium carbonate 134 mg (1.Ommo 1), palladium acetate 9.Omg ( After adding 0.440 mmo 1) to water (0.40 ml), the mixture was stirred at 75 ° C. for 5 hours. After cooling to room temperature, the mixture was diluted with chloroform, washed with water, dried (magnesium sulfate), and concentrated under reduced pressure.
  • N-Methyl-1- (2-methyl-5-bromophenyl) _2-Methoxyimino propionamide 10 Omg (0.33 mmo 1), 3,4-Dimethylphenyl boronic acid 60 mg (0.4 Ommo 1), odor Tetra-n-butynoleammonium 110 mg (0.34 mmo 1), potassium carbonate 114 mg (0.83 mmo 1), palladium acetate 7.4 mg (0.033 mmo 1) (0.40 ml), followed by stirring at 75 ° C for 7 hours. After cooling to room temperature, the reaction mixture was diluted with chloroform, washed with water, dried (magnesium sulfate), and concentrated under reduced pressure.
  • Methyl 2-acetylamide 3- (5-bromo-12-methylphenyl) acrylate (compound represented by formula [8] below) 91 g (292 mmo 1) and methoxyamine hydrochloride 26.1 g (31 Concentrated hydrochloric acid (26 ml) was added to a solution of 2 mmol in methanol (1600 ml). Stir at reflux temperature for 44 hours After that, the solvent was distilled off under reduced pressure, and the residue was diluted with chloroform.
  • N-methyl- 3- ( 5 -bromo-12-methylphenyl) -12- (methoxyimino) propanamide is reacted with 3-fluorophenylboric acid to give N-methyl- 3 Methyl-1- [5- (3-fluorophenyl) -2-methylphenyl] _2- (methoxyximino) propanamide (Compound 19 of the present invention) was obtained.
  • N-methyl-3- (5-bromo-2-methylphenyl) -12- (methoxyimino) propanamide is reacted with 4-fluorophenylboric acid to give N-methyl-3 Methyl-3- [5- (4-fluorophenyl) -12-methylphenyl] -2- (methoxyimino) propanamide (Compound 20 of the present invention) was obtained.
  • Production example 1 3 By reacting N-methyl-1- (5-bromo-2-methylphenyl) -12- (methoxyimino) propanamide with 4-trifluorophenylboric acid according to the method of Production Example 2, N-methyl-1- [2-methyl-5- (4-trifluoromethylphenyl) phenyl] -12- (methoxyimino) propanamide (Compound 25 of the present invention) was obtained.
  • Methyl 3- (5-bromo-1-2-methyl) phenyl-1- (methoximino) propanoate 443mg (1.47mmo1), bis (pinacolato) diboron 410mg (1.61mmo1), [ 1,1'-bis (diphenylphosphino) phenicene] dichloropalladium (II) chloride dimethylene complex 6 Omg (0.073 mmo 1) and potassium acetate 432 mg (4.40 mmo 1) in dimethyl sulfoxide 1 After adding to 1 ml, the mixture was stirred at 80 ° C for 8 hours.
  • N-methyl-3- (5-bromo-1-methylphenyl) _2- (methoxyimino) propionamide 598 mg (2.0 mm o 1), tert-butynoleacetylene 1.50 g (18 mm o 1) dichlorobis [hereinafter referred to as Pd C l 2 (PPh 3) 2] ( bird whistle two Honoré phosphine) palladium (II) 69mg (0. 098m mo 1), copper iodide 53 mg (0.
  • N-methyl-3- (5-bromo-2-methinolephenyl) _2- (methoxyimino) propionamide 596 mg (2.0 mmo 1), phenylacetylene 306 mg (3.0 mmol), PdC 1 2 (PP h 3) 2 4 Omg (0. 056 mm o 1), copper iodide 1 5mg (0. 079 mm o 1 ), bird whistle two Honoré phosphine 6 Omg (0. 23mm o 1) and Toryechiruamin 1. After 5 ml was added to 6 ml of acetonitrile, the mixture was refluxed for 9 hours under a nitrogen atmosphere.
  • N-methyl-3- (5-promo-2-methylphenyl) -12- (methoxyimino) propanamide is reacted with triethylsilylacetylene to give N-methyl-3- ⁇ 2- Methyl-5- (2-triethylsilylletini ) -2-phenyl-2- (methoxyimino) propanamide (Compound 251 of the present invention).
  • N-methyl-3- (5-bromo-12-methylphenyl) -12- (methoxyimino) propanamide is reacted with propargyltrimethylsilane to give N-methyl-3- [2- Methyl-5- (3-trimethylsilyl-1- 1-ethynyl)] phenyl-2-methoxyiminopropanamide (Compound 275 of the present invention) was obtained.
  • N-methyl-3- (5-bromo-12-methylphenyl) -12- (methoxyimino) propanamide is reacted with propargylbenzene to obtain N-methyl-3- [2- 5- (3-phenylenol-1-propiel)] phenyl-2-methoximinopropanamide (Compound 291 of the present invention) was obtained.
  • diluted hydrochloric acid prepared by mixing 21 ml of concentrated hydrochloric acid and 130 ml of water
  • the resulting solution was filtered through cotton, washed with a black hole form, and the filtrate was separated. After the aqueous layer was extracted once more with chloroform, the organic layers were combined, washed with water, dried, and concentrated.
  • a mixture of an equal amount of tert-butyl methyl ether and n- hexane is added to the solid residue, and the mixture is stirred at room temperature for a while.
  • N-methyl-3- (5-acetinol-2-methylphenyl) -2- (methoxymino) propanamide (Compound 31 of the present invention) 262 mg was dissolved in 4 ml of methanol, and 134 mg of propoxyamine hydrochloride was added thereto. (1.2 mmoi) and 95 mg (l. 2 mmol) of pyridine were added, and the mixture was stirred at room temperature for 8 hours. After most of the methanol was distilled off, ethyl acetate was added to the residue, and the mixture was washed successively with a dilute aqueous hydrochloric acid solution, a dilute aqueous sodium bicarbonate solution and water. The organic layer was dried and concentrated.
  • N-methyl-3- (5-promo-1-methylphenyl) -12- (methoximino) propanamide was reacted with 3-methoxy-3-methyl-1-butyne to give N —Methyl-3 -— ⁇ 2-Methyl-5— (3-Methoxy-3—Methyl-1-butyr) ⁇ Fenryl-2 -— (Methoxyimino) propanamide
  • N-methyl-3- (5-bromo-2-methylphenyl) -12- (methoxyimino) propanamide was reacted with 3-methoxy-13-ethyl-1-pentyne N-methyl-3— ⁇ 2-methyl-5- (3-methoxy-3-ethyl-11-pentinole) ⁇ phenyl 2- (methoxyimino) propanamide (Compound 2777 of the present invention) was.
  • Production Example 48 According to the method of Production Example 16, methyl 3- ⁇ 5- (4,4,5,5-tetramethyl-1,3,2-dioxoborolael) -1-methyl ⁇ feninole 2- (methoxymethoxy) ) Propanoate reacts with 2-bromo-6-chloropyridine to give methyl 3- ⁇ 2-methinole-5- (6-chloro-1-pyridinyl) ⁇ phenyl-2- (propoxyimino) propanoate (Compound of the present invention 1 118) was obtained.
  • Production Example 51 According to the method of Production Example 17, methyl 3- ⁇ 2-methyl-5- (6-trifluoromethyl-12-pyridinyl) ⁇ phenol-12-methoxyiminopropanoate and 40% methanol of methylamine The solution is allowed to react, and N-methyl-3- ⁇ 2-methinole-5- (6-triphneololomethyl-2-pyridinole) ⁇ phen-nore-2- (methoxyimino) propanamide (Compound 354 of the present invention) ).
  • Me is a methyl group
  • Et is an ethyl group
  • n-Pr is a propyl group
  • i-Pr is an isopropyl group
  • c-Pr is a cyclopropyl group
  • n -Bu is a butyl group
  • i-Bu is an isobutyl group
  • tert-Bu is a tert-butyl group
  • sec-Bu is a sec-butyl group
  • c-Bu is a cyclobutynole group
  • n-P ent is a pentyl group
  • c-Pent is a cyclopentyl group
  • n-Hex is a hexyl group
  • c-HeX is a cyclohexyl group
  • Ph is a phenyl group
  • Py is a pyridyl group
  • Ac represents an acet
  • each of the compounds of the present invention 1 to 400 and 1001 to: 1400, 3 parts of calcium lignosnolefonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic silicon oxide hydroxide are thoroughly pulverized and mixed to obtain each wettable powder. .
  • Each of the emulsions is obtained by thoroughly mixing 20 parts of each of the compounds 1 to 400 and 1001 to 1400 of the present invention, 14 parts of polyoxyethylene styrene diphenyl ether, 6 parts of calcium dodecyl benzene sulfonate and 60 parts of xylene.
  • Each of the emulsions is obtained by thoroughly mixing 5 parts of each of the present compounds 1 to 400 and 1001 to 1400, 14 parts of polyoxyethylene styrene phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.
  • each flowable agent 10 parts of each of the present compounds 1 to 400 and 1001 to 1400, 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt, and 55 parts of water are mixed and pulverized by a wet pulverization method. Thus, each flowable agent is obtained.
  • each of the present compounds 1 to 400 and 1001 to 1400 are dissolved in 5 parts of xylene and 5 parts of trichloroethane, and mixed with 89.9 parts of deodorized kerosene to obtain 0.1% oil solution of each.
  • Test Examples show that the compounds of the present invention are useful as agricultural and horticultural fungicides and insecticides and acaricides.
  • this invention compound is shown by the compound number of Table 1-Table 22.
  • the control effect of the compound of the present invention was evaluated by visually observing the area of the lesion on the test plant at the time of the survey and comparing the area of the lesion in the untreated section with the area of the lesion in the section treated with the compound of the present invention. did.
  • Test example 1 Rice blast control test (preventive effect)
  • Plastic pots were filled with sandy loam, rice (Nipponbare) was sown, and grown in a greenhouse for 20 days. Thereafter, the compounds of the present invention 1, 2, 4, 5, 7, 12, 14, 15, 15, 19, 20, 25, 88, 110, 151, 153, 164, 251, 275, 286, 291 , 294, 1001, 1007, 1 088, 1 1 10, 1 25 1, 365, 1368, 368, 1376, 376, 1375, 375, 137 ⁇ , 370, 1 1 1 7, 1 1 7, 1 1, 1 8, 354, 1 356, 356 and 1 2 94 each of after a suspension concentrate according to formulation example 2 was diluted with water to a predetermined concentration (500 p P m), it is sufficient adhering to the rice leaf surface Foliage was sprayed as follows.
  • a predetermined concentration 500 p P m
  • the plants were air-dried and sprayed with a flowable solution of the blast fungus. After inoculation, the plants were placed in a humid environment at 28 ° C for 6 days, and the control effect was examined.
  • Test example 2 Wheat powdery mildew control test (Therapeutic effect)
  • a plastic pot was filled with sandy loam, and wheat (Norin 73) was sown and grown in a greenhouse for 10 days.
  • the wheat seedlings that had developed the second leaf were sprinkled with wheat powdery mildew spores and inoculated. After inoculation, they were placed in a greenhouse at 23 ° C for 2 days.
  • Formulation of each of the present compounds 1, 2, 4, 5, 7, 12, 14, 19, 20, 25, 88, 151, 164, 251, 286, 1001, 1007, 1088 and 1251 After a flowable preparation was prepared according to Example 2, it was diluted with water to a predetermined concentration (500 ppm), and sprayed so that it adhered sufficiently to the leaves of wheat inoculated with powdery mildew.
  • the compounds of the present invention 1, 2, 4, 5, 7, 12, 14, 14, 19, 20, 25, 88, 151, 164, 251, 286, 1001, 1007, 1088 and 1251
  • the lesion area on the plant in the treated plot was less than 10% of the lesion area in the untreated plot.
  • Test example 3 Wheat rust control test (preventive effect)
  • a plastic pot was filled with sandy loam, and wheat (Norin 73) was sown and grown in a greenhouse for 10 days.
  • Compounds of the invention 1, 2, 4, 5, 7, 12, 14, 15, 15, 19, 20, 88, 110, 151, 153, 164, 251, 275, 286, 291, 294, 1001, 1007, 1 088, 1 1 10, 1 251, 36 5, 1 368, 368, 1 376, 376, 1 375, 375, 1370, 37 0, 1 1 1 7, 1 1 7, 1 1 8 , 354, 1356, 356 and 1253 were made into flowables according to Formulation Example 2 and then diluted with water to a predetermined concentration (500 ppm) so that they adhered well to the wheat leaves. Foliage.
  • the plants were air-dried and inoculated with spores of wheat leaf rust. After inoculation, the plants were kept at 23 ° C and in a dark and humid environment for one day, and then kept under lighting for 6 days.
  • the compounds of the present invention 1, 2, 4, 5, 7, 12, 12, 14, 15, 19, 20, 88, 11
  • Test example 4 Wheat blight control test (preventive effect)
  • a plastic pot was filled with sandy loam, and wheat (Norin 73) was sown and grown in a greenhouse for 10 days.
  • Compounds of the present invention 1, 2, 4, 5, 7, 12, 19, 20, 88, 110, 151, 153, 164, 275, 286, 291, 294, 1001, 1370, 1 1
  • Foliage was sprayed. After spraying, the plants were air-dried and sprayed with a spore flowable solution of wheat wilt.
  • the plants were placed at 15 ° C, in a dark and humid environment for 4 days, and then placed under illumination for 7 days.
  • the compounds of the present invention 1, 2, 4, 5, 7, 12, 19, 20, 88, 11.0, 151, 15 3, 1 64, 275, 286, 291, 294, 1001, 1370
  • the area of the lesion on the plants in the,, 117, 354, 356 and 1110 treatments was less than 10% of the lesion area in the untreated treatment.
  • Test Example 5 Wheat eye spot control test (preventive effect)
  • a plastic pot was filled with sandy loam, and wheat (Norin 73) was sown and grown in a greenhouse for 10 days.
  • Compounds of the invention 1, 4, 5, 7, 12, 15, 19, 20, 25, 88, 110, 151, 153, 164, 286, 294, 1251, 351, 370, 1 18 , 356 and 1253 were each made into a flowable agent in accordance with Preparation Example 2, diluted with water to a predetermined concentration (500 ppm), and sprayed with foliage so as to sufficiently adhere to the wheat leaf surface. After spraying, the plants were air-dried and inoculated with a mashed potato containing spores of wheat eye spot disease fungus.
  • Test Example 6 Grape downy mildew control effect test (preventive effect) Plastic pots were filled with sandy loam, sown with grapes (Beriichi A), and grown in a greenhouse for 40 days. Compounds of the present invention 1, 2, 4, 5, 7, 12, 14, 15, 15, 19, 20, 25, 88, 110, 15 3, 1 64, 25 1, 27 5, 28 86, 29 91, 294, 1000, 1 108, 1 1 1 0, 1 2 5 1, 1 2 5 3, 3 5 1, 1 3 6 8, 3 6 8 , 1376, 376, 1375, 370, 1178 and 1294 were made into flowables according to Formulation Example 2 and then diluted with water to the specified concentration (200ppm) It was sprayed with foliage so that it adhered well to the grape leaf surface.
  • the plants were air-dried and sprayed with a zoosporang flowable solution of grape downy mildew. After inoculation, the plants were placed at 23 ° C and a high humidity for one day, and then placed in a greenhouse for 6 days, and the control effect was investigated.
  • the compounds of the present invention 1, 2, 4, 5, 7, 12, 14, 14, 15, 19, 20, 25, 88, 110, 15 3, 1 64, 25 1, 2 7 5, 2 8 6, 2 9 1, 2 94, 1 0 0 1, 1 0 8 8, 1 1 1 0, 1 2 5 1, 1 2 5 3, 3 5 1, 1 3 6 8 , 36 8, 1 37 6, 3 76, 1 3 7 5, 3 70, 1 18 and 1 294
  • the lesion area on the plants in the treated area was 10% of the lesion area in the untreated area It was below.
  • Test Example 7 Control test of cucumber gray mold (preventive effect)
  • Plastic pots were filled with sandy loam, sown with cucumber (Sagami Hanjiro), and grown in a greenhouse for 12 days.
  • Compounds of the present invention 1, 2, 4, 7, 12, 14, 15, 15 1, 153, 164, 286, 294, 1001, 1007, 1088, 1
  • Each of 25 1, 1 18 and 1 294 was made into a flowable agent according to Formulation Example 2 and diluted with water to a predetermined concentration (500 ppm) so that it adhered sufficiently to the leaves of the cucumber Foliage was sprayed. After spraying, the plants were air-dried, and a PDA medium containing hyphae of the fungus gray fungus was placed on the leaves of cucumber.
  • Test Example 8 Test for the control effect of cucumber powdery mildew
  • Plastic pots were filled with sandy loam, sown with cucumber (Sagami Hanjiro), and grown in a greenhouse for 12 days.
  • Compounds of the present invention 1, 2, 4, 5, 7, 12, 14, 19, 2 0, 25, 88, 1 51, 1 64, 251, 275, 286, 294, 100
  • Each of 1, 1007, 1088, 1251, 368, 1376, 370, 354 and 1294 was made into a flowable agent according to Formulation Example 2, then diluted with water to a predetermined concentration (200 ppm), and the The foliage was sprayed so as to sufficiently adhere to the surface. After spraying, the plants were air-dried and inoculated with spores of the powdery mildew fungus. After 12 days at 23 ° C after inoculation, the control effect was investigated.
  • the compounds of the present invention 1, 2, 4, 5, 7, 12, 14, 19, 20, 25, 88, 151, 164, 251, 275, 286, 294, 1001, 1007, 1088,
  • the lesion area on the plants in the 251, 368, 1376, 370, 354 and 1294 treatments was less than 10% of the lesion area in the untreated treatment.
  • Test Example 9 Wheat powdery mildew control effect test (preventive effect)
  • a plastic pot was filled with sandy loam, and wheat (Norin 73) was sown and grown in a greenhouse for 10 days.
  • Compounds of the present invention 110, 153, 275, 291, 294, 1 110, 1 253, 351, 365, 1 368, 368, 1 376, 376, 1 375, 375, 1 370, 1 1 17,
  • Each of 117, 118, 354, 1356, 356, and 1294 was made into a flowable agent according to Formulation Example 9, then diluted with water to a predetermined concentration (500 ppm), and then applied to the wheat leaf surface. The foliage was sprayed so as to adhere sufficiently. After spraying, the plants were air-dried.
  • the compounds of the present invention 110, 153, 275, 291, 294, 1110, 1253, 351, 365, 1368, 368, 1376, 376, 1375, 375, 1370, 11
  • the lesion area on plants in the treated areas on 17, 17, 117, 118, 354, 1356, 356 and 1294 was less than 10% of the lesion area in the untreated area.
  • Test example 10 Acaricidal test against Nami-hamada (Tetranychus urticae)
  • Plastic pots were filled with sandy loam, and rice (sunny Nihon) was sown and grown in a greenhouse for 20 days. Thereafter, the compound of the present invention 1253 was made into a flowable agent in accordance with Preparation Example 9, and diluted with water to a predetermined concentration (500 ppm), and sprayed onto the foliage of the rice so as to fully adhere to the rice leaf surface. did. After spraying, the plants were air-dried, and about 30 larvae of Brassica napus were released. After being released in a greenhouse for 6 days, their survival was examined, and the mortality was 80% or higher.
  • Test Example 1 2 Insecticidal test on housefly (Musca domestica)
  • a filter paper of the same size was placed on the bottom of a polyethylene cup having a diameter of 5.5 cm, and a water-diluted solution (50 ppm) of the compound 25 1 of the present invention obtained in accordance with Formulation Example 9 was used. 7 ml was dropped on a filter paper, and about 3 O mg of sucrose was uniformly added as feed. Ten female female house flies were released into them, covered with a lid, and one day later, their viability was examined to determine the mortality. As a result, the compound 251 of the present invention exhibited a mortality of 80% or more.
  • the compound of the present invention has excellent plant disease control and insecticidal and acaricidal effects.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne des dérivés d'oxime représentés à l'aide de la formule générale (1), présentant de très bons effets, qui permettent d'endiguer des maladies de plantes, ainsi que des activités insecticides et acaricides. Dans cette formule R1 est un groupe alkyle en C¿1?-C10, ou une autre molécule du même genre, éventuellement substitué, un des U et V est un groupe CR?2¿ et l'autre est un groupe CH ou N, et W est un groupe CR3 ou N (dans lequel R2 et R3 sont chacun, et de manière indépendante, un groupe hydrogène, halogène, alkyle en C¿1?-C6, ou un groupe du même genre), et Y est un groupe oxygène ou NH.
PCT/JP2000/000060 1999-01-12 2000-01-11 Derives d'oxime et utilisations associees WO2000041999A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU18922/00A AU1892200A (en) 1999-01-12 2000-01-11 Oxime derivatives and uses thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP521899 1999-01-12
JP11/5218 1999-01-12
JP22630899 1999-08-10
JP11/226308 1999-08-10

Publications (1)

Publication Number Publication Date
WO2000041999A1 true WO2000041999A1 (fr) 2000-07-20

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AU (1) AU1892200A (fr)
WO (1) WO2000041999A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8455489B2 (en) * 2003-11-10 2013-06-04 Exelixis, Inc. Substituted pyrimidine compositions and methods of use
WO2020027214A1 (fr) 2018-07-31 2020-02-06 住友化学株式会社 PROCÉDÉ DE LUTTE CONTRE LA ROUILLE DU SOJA RÉSISTANT AUX INHIBITEURS DE Qo

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5312962A (en) * 1991-07-10 1994-05-17 Bayer Aktiengesellschaft Process for the production of compounds containing aldimine or ketimine groups and the compounds obtained by this process
US5354779A (en) * 1991-12-09 1994-10-11 Bayer Aktiengesellschaft Substituted oxime ether amides
WO1998045254A2 (fr) * 1997-04-08 1998-10-15 Sumitomo Chemical Company, Limited Composes d'oxime, leur utilisation et intermediaires pour leur production

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5312962A (en) * 1991-07-10 1994-05-17 Bayer Aktiengesellschaft Process for the production of compounds containing aldimine or ketimine groups and the compounds obtained by this process
US5354779A (en) * 1991-12-09 1994-10-11 Bayer Aktiengesellschaft Substituted oxime ether amides
WO1998045254A2 (fr) * 1997-04-08 1998-10-15 Sumitomo Chemical Company, Limited Composes d'oxime, leur utilisation et intermediaires pour leur production

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8455489B2 (en) * 2003-11-10 2013-06-04 Exelixis, Inc. Substituted pyrimidine compositions and methods of use
WO2020027214A1 (fr) 2018-07-31 2020-02-06 住友化学株式会社 PROCÉDÉ DE LUTTE CONTRE LA ROUILLE DU SOJA RÉSISTANT AUX INHIBITEURS DE Qo

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