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WO2009048152A2 - Composé imine insaturée et son utilisation pour la protection phytosanitaire - Google Patents

Composé imine insaturée et son utilisation pour la protection phytosanitaire Download PDF

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Publication number
WO2009048152A2
WO2009048152A2 PCT/JP2008/068522 JP2008068522W WO2009048152A2 WO 2009048152 A2 WO2009048152 A2 WO 2009048152A2 JP 2008068522 W JP2008068522 W JP 2008068522W WO 2009048152 A2 WO2009048152 A2 WO 2009048152A2
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group
compound
optionally substituted
cdcl
propenylidene
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WO2009048152A3 (fr
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Shigeyuki Itoh
Takashi Kuragano
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/45—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom not containing sulfur-to-oxygen bonds, e.g. polysulfides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—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
    • 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
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Definitions

  • the present invention relates to an ⁇ , ⁇ -unsaturated imine compound and use thereof for pest control .
  • Japanese Patent Application National Publication (Laid-Open) No. 10-513502 describes an ⁇ , ⁇ -unsaturated imine compound useful as a coloring agent or stabilizer.
  • the present invention has an object of providing a compound showing an excellent controlling effect on pests.
  • the present inventors have intensively studied and resultantIy found that an ⁇ , ⁇ -unsaturated imine compound of the following formula (I) shows an excellent controlling effect on pests, leading to the present invention.
  • the present invention includes the following inventions .
  • A represents a phenyl group optionally substituted with (X 2 ) q/ an aromatic hetero ring optionally substituted with a Cl to C5 alkyl group or a halogen atom, a Cl to C5 alkyl group optionally substituted with a halogen atom, or a C3 to ClO cycloalkyl group optionally substituted with a Cl to C5 alkyl group or a halogen atom, where the aromatic hetero ring forms a carbon-to-carbon bond with the main chain of the compound,
  • R represents a hydrogen atom or a Cl to C5 alkyl group optionally substituted with a halogen atom
  • each of p, q and r represents an integer of 0 to 5
  • R 1 represents a Cl to C5 chain hydrocarbon group optionally substituted with at least one of the group A,
  • R 2 represents a Cl to C5 chain hydrocarbon group or a hydrogen atom
  • R 3 represents a Cl to C6 chain hydrocarbon group optionally substituted with at least one of the group A, or a hydrogen atom
  • the group A consists of Cl to C5 alkyloxy groups, Cl to C5 alkylthio groups and halogen atoms
  • the group B consists of Cl to C6 alkyl groups, Cl to C5 alkyloxy groups, Cl to C5 alkylthio groups and halogen atoms .
  • X 1 , X 2 and X 3 respectively represent -OR 1 , -SR 1 , a Cl to C6 chain hydrocarbon group optionally substituted with at least one of the group A, a phenyl group optionally substituted with at least one of the group B, a nitro group, a cyano group or a halogen atom, or in case that p, q or r represents 2 or more, two X 1 S, two X 2 S or two X 3 S may together form a C2 to C5 polymethylene group optionally substituted with at least one of the group B, a propene-1, 3-diyl group optionally substituted with at least one of the group B, a 1,3- butadiene-1, 4-diyl group optionally substituted with at least one of the group B, or a methylenedioxy group.
  • X 1 , X 2 and X 3 respectively represent a Cl to C ⁇ alkyl group optionally substituted with at least one of the group A, -OR 1 , a phenyl group optionally substituted with at least one of the group B, a nitro group, a cyano group or a halogen atom, or in case that p, q or r represents 2 or more, two X 1 S, two X 2 S or two X 3 S may together form a C2 to C5 polymethylene group, a propene-1, 3-diyl group, or a 1,3- butadiene-1, 4-diyl group,
  • R 1 represents a Cl to C5 alkyl group optionally substituted with at least one of the group A.
  • X 1 represents a Cl to C6 alkyl group optionally substituted with a halogen atom, a Cl to C5 alkyloxy group optionally substituted with a halogen atom, a nitro group or a halogen atom.
  • X 2 represents a nitro group, a halogen atom, a Cl to C6 alkyl group optionally substituted with a halogen atom, a Cl to C5 alkyloxy group optionally substituted with a halogen atom, or a phenyl group optionally substituted with at least one of the group consisting of Cl to C6 alkyl groups, Cl to C5 alkyloxy groups and halogen atoms.
  • (7) The ⁇ , ⁇ -unsaturated imine compound according to any one of (1) to (6) , wherein
  • X 3 represents a Cl to C6 alkyl group optionally substituted with a halogen atom, a Cl to C5 alkyloxy group optionally substituted with a halogen atom, a halogen atom, or a phenyl group optionally substituted with at least one of the group consisting of Cl to C6 alkyl groups, Cl to C5 alkyloxy groups and halogen atoms, or a C2 to C5 polymethylene group formed by two X 3 S together.
  • (8) The ⁇ , ⁇ -unsaturated imine compound according to any one of (1) to (7) , wherein
  • X 1 represents a Cl to C6 alkyl group optionally substituted with a halogen atom, a Cl to C5 alkyloxy group optionally substituted with a halogen atom, a nitro group or a halogen atom,
  • X 2 represents a nitro group, a halogen atom, a Cl to C6 alkyl group optionally substituted with a halogen atom, a Cl to C5 alkyloxy group optionally substituted with a halogen atom, or a phenyl group optionally substituted with at least one of the group consisting of Cl to C5 alkyl groups, Cl to C5 alkyloxy groups and halogen atoms
  • X 3 represents a halogen atom, a Cl to C6 alkyl group optionally substituted with a halogen atom, a Cl to C5 alkyloxy group optionally substituted with a halogen atom, or a phenyl group optionally substituted with at least one of the group consisting of Cl to C5 alkyl groups, Cl to C5 alkyloxy groups and halogen atoms, or a C2 to C5 polymethylene group formed by two X 3 S together.
  • a pesticidal composition comprising as an active ingredient the ⁇ , ⁇ -unsaturated imine compound as described in any one of (1) to (9) .
  • a pest controlling method which comprises applying the OL, ⁇ -unsaturated imine compound as described in any one of (1) to (9) to a pest or a place where the pest inhabits.
  • the compound of the present invention shows an excellent controlling effect on pests.
  • the aromatic hetero ring includes 5-membered rings or 6-membered ring having a nitrogen atom; 5-membered rings having an oxygen atom; 5- membered rings having a sulfur atom.
  • aromatic hetero ring examples include furane, thiophene, pyrrole, thiazole, imidazole, pyridine, pyrimidine and pyrazine.
  • the aromatic hetero ring forms a carbon-to-carbon bond with the main chain of the compound .
  • the halogen atom means a fluorine atom, chlorine atom, bromine atom and iodine atom.
  • examples of the Cl to C5 alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group and pentyl group .
  • examples of the C3 to ClO cycloalkyl group include a cyclopropane group, cyclobutane group, cyclopentane group and cyclohexane group.
  • the group A means a group consisting of Cl to C5 alkyloxy groups, Cl to C5 alkylthio groups and halogen atoms .
  • the group B means a group consisting of Cl to C6 alkyl groups, Cl to C5 alkyloxy groups, Cl to C5 alkylthio groups and halogen atoms.
  • Groups of the group A include, for example, a methoxy group, ethoxy group, propoxy group, isopropoxy group; methylthio group, ethylthio group, propylthio group, isopropylthio group; fluorine atom, chlorine atom and bromine atom.
  • Groups of the group B include, for example, a methyl group, ethyl group, propyl group, isopropyl group; methoxy group, ethoxy group, propoxy group, isopropoxy group; methylthio group, ethylthio group, propylthio group, isopropylthio group; fluorine atom, chlorine atom and bromine atom.
  • the Cl to C6 chain hydrocarbon group optionally substituted with at least one of the group A includes Cl to C6 alkyl groups optionally substituted with at least one of the group A, C2 to C ⁇ alkenyl groups optionally substituted with at least one of the group A and C2 to C6 alkynyl groups optionally substituted with at least one of the group A.
  • Cl to C6 alkyl group optionally substituted with at least one of the group A examples include Cl to C6 alkyl groups such as a methyl group, a ethyl group, a propyl group, an isopropyl group, a butyl group, a tert- butyl group, or a pentyl group; Cl to C6 haloalkyl groups such as a trifluoromethyl group; and Cl to C5 alkyloxy-Cl to C6 alkyl groups such as a methoxymethyl group, a 2- methoxyethyl group, or a 2-ethoxyethyl group.
  • Examples of the C2 to C6 alkenyl group optionally substituted with at least one of the group A include C2 to C6 alkenyl groups such as a vinyl group, a 2-propenyl group, or a 2-butenyl group; and C2 to C6 haloalkenyl groups such as a 1-chlorovinyl group.
  • Examples of the C2 to C6 alkynyl group optionally substituted with at least one of the group A include C2 to C6 alkynyl groups such as a 2-propynyl group, or a 2- butynyl group .
  • R 1 represents a Cl to C5 chain hydrocarbon group optionally substituted with at least one of the group A.
  • R 2 represents a Cl to C5 chain hydrocarbon group or hydrogen atom.
  • R 3 represents a Cl to C6 chain hydrocarbon group optionally substituted with at least one of the group A, or a hydrogen atom.
  • the above-described Cl to C5 chain hydrocarbon group includes Cl to C5 alkyl groups, C3 to C5 alkenyl groups and C3 to C5 alkynyl groups .
  • examples of the C3 to C5 alkenyl group include a 2-propenyl group and 2-butenyl group .
  • examples of the C3 to C5 alkynyl group include a 2-propynyl group and 2-butynyl group .
  • the -OR 1 includes Cl to C5 alkyloxy groups optionally substituted with at least one of the group A, C3 to C5 alkenyloxy groups optionally substituted with at least one of the group A and C3 to C5 alkynyloxy groups optionally substituted with at least one of the group A.
  • Cl to C5 alkyloxy group optionally substituted with at least one of the group A examples include Cl to C5 alkyloxy groups such as a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a tert-butoxy group, or a pentyloxy group; and Cl to C5 haloalkyloxy groups such as a trifluoromethoxy group.
  • Examples of the C3 to C5 alkenyloxy group optionally substituted with at least one of the group A include C3 to C5 alkenyloxy groups such as a 2-propenyloxy group.
  • Examples of the C3 to C5 alkynyloxy group optionally substituted with at least one of the group A include C3 to C5 alkynyloxy groups such as a 2-propynyloxy group.
  • the -SR 1 includes Cl to C5 alkylthio groups optionally substituted with at least one of the group A, C3 to C5 alkenylthio groups optionally substituted with at least one of the group A and C3 to C5 alkynylthio groups optionally substituted with at least one of the group A.
  • Cl to C5 alkylthio group optionally substituted with at least one of the group A examples include Cl to C5 alkylthio groups such as a methylthio group, ethylthio group, propylthio group, isopropylthio group, or butylthio group .
  • Examples of the C3 to C5 alkenylthio group optionally substituted with at least one of the group A include C3 to C5 alkenylthio groups such as a 2-propenyloxy group.
  • Examples of the C3 to C5 alkynylthio group optionally substituted with at least one of the group A include C3 to C5 alkynylthio groups such as a 2-propynyloxy group.
  • Examples of -N (R 2 ) R 1 include Cl to C5 alkylamino groups such as a methylamino group, ethylamino group; and di (Cl to C5 alkyl) amino groups such as a dimethylamino group, or a diethylamino group.
  • the phenyl group optionally substituted with at least one of the group B includes a phenyl group, 4-methylphenyl group, 4-chlorophenyl group and 4-fluorophenyl group.
  • the C2 to C5 polymethylene group optionally substituted with at least one of the group B includes an ethylene group, propane-1, 3-diyl group, namely trimethylene group, butane-1, 4-diyl group, namely tetramethylene group, and 2, 2, 3, 3 -tetramethylbutane-1, 4-diyl group.
  • Examples of the propene-1, 3-diyl group optionally substituted with at least one of the group B include a propene-1, 3-diyl group and 2 -methyl-1-propene-1, 3-diyl group.
  • Examples of the 1, 3 -butadiene-1, 4-diyl group optionally substituted with at least one of the group B include a 1, 3 -butadiene-1, 4-diyl group, 2-methyl-l, 3- butadiene-1, 4-diyl group, 2-chloro-l, 3 -butadiene-1, 4-diyl group and 2 , 3-dichloro-l, 3 -butadiene-1, 4-diyl group.
  • the above-described compound (I) has a phenyl group optionally substituted with (X 1 J p , a phenyl group optionally substituted with (X 2 ) g and a phenyl group optionally substituted with (X 3 ) r .
  • Suitable examples of the phenyl group optionally substituted with (X 1 Jp include a phenyl group, 2- fluoropheny1 group, 3 -fluoropheny1 group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4- chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2 -methylphenyl group, 3- methylphenyl group, 4 -methylphenyl group, 2- trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-methoxyphenyl group, 3- methoxyphenyl group, 4 -methoxyphenyl group, 2- (methylthio) phenyl group, 4- (methylthio) phenyl group, 2- nitrophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 2 -cyanopheny1 group
  • Suitable examples of the phenyl group optionally substituted with (X 2 ) q include a phenyl group, 2- fluorophenyl group, 3 -fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4- chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-methylphenyl group, 3- methylphenyl group, 4 -methylphenyl group, 4-isopropylphenyl group, 2-trifluoromethylphenyl group, 3- trifluoromethylphenyl group, 4 -trifluoromethylphenyl group, 2 -methoxyphenyl group, 3 -methoxyphenyl group, 4- methoxyphenyl group, 2- (methylthio) phenyl group, 4- (methylthio) phenyl group, 2-nitrophenyl group, 3- nitrophenyl group, 4-
  • Suitable examples of the phenyl group optionally substituted with (X 3 ) r include a phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4 -fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4- chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-methylphenyl group, 3- methylphenyl group, 4 -methylphenyl group, 4-isopropylphenyl group, 2 -trifluoromethylphenyl group, 3- trifluoromethylphenyl group, 4 -trifluoromethylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4- methoxyphenyl group, 2- (methylthio) phenyl group, 4- (methylthio) phenyl group, 2-nitrophenyl group, 3- nitrophenyl group, 4-nitrophen
  • Embodiments of the compound (I) include the following embodiments ; ex, ⁇ -unsaturated imine compounds of the formula (I) in which X 1 represents a Cl to C6 chain hydrocarbon group optionally substituted with at least one of the group A, - OR 1 , -SR 1 , a phenyl group optionally substituted with at least one of the group B, a nitro group, a cyano group or a halogen atom, or in case that p is 2 or more, two X 1 S form together a C2 to C5 polymethylene group optionally substituted with at least one of the group B, a propene- 1,3-diyl group optionally substituted with at least one of the group B, a 1, 3 -butadiene-1, 4-diyl group optionally substituted with at least one of the group B, or a methylenedioxy group, ⁇ , ⁇ -unsaturated imine compounds of the formula (I) in which X 1 represents a
  • the compound of the present invention can be produced, for example, by the following production method. Production Method 1
  • This reaction can be carried out in the presence of a suitable solvent .
  • a suitable solvent include alcohols such as methanol, ethanol , or isopropanol ; aliphatic hydrocarbons such as pentane, hexane, heptane, or petroleum ether; aromatic hydrocarbons such as benzene, toluene, or xylene; esters such as methyl acetate, ethyl acetate, ethyl formate, or ethyl propionate; ketones such as acetone, or methylethylketone; ethers such as diethylether, dipropylether, diisopropylether, dibutylether, tetrahydrofuran, or dioxane; nitriles such as acetonitrile, or propionitrile; acid amides such as dimethylformamide, or dimethylacetamide; sulfoxides such as dimethyl sulfoxide, or
  • a base or an acid may be present in the reaction system, if necessary.
  • examples of such a base include alkali metal alcoholates such as sodium ethylate, sodium methylate, or potassium tert-butoxide; nitrogen-containing organic compounds such as triethylamine, diisopropylethylamine, pyridine, 4- dimethylaminopyridine, or N,N-dimethylaniline; carbonates such as potassium carbonate, sodium carbonate, sodium hydrogen carbonate, or potassium hydrogen carbonate; hydroxides such as sodium hydroxide, or potassium hydroxide; metal hydrides such as lithium hydride, sodium hydride, or potassium hydride; and organolithiums such as butyllithium, or lithiumdiisopropylamide .
  • the amount of the base to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and it is preferably 0.01 to 0.5 equivalents, more preferably 0.01 to 0.2 equivalents to the compound (ID -
  • Examples of such an acid include mineral acids such as hydrochloric acid, sulfuric acid, or nitric acid; organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, methanesulfonic acid, benzenesulfonic acid, or p-toluenesulfonic acid; acid addition salts of amines such as triethylamine hydrochloride, or pyridine hydrochloride; and Lewis acids such as aluminum chloride, zinc chloride, zinc iodide, titanium tetrachloride, cerium chloride, ytterbium triflate, or boron trifluoride-ether complex.
  • the amount of the acid to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and it is preferably 0.01 to 0.5 equivalents, more preferably 0.01 to 0.2 equivalents to the compound (II) .
  • the reaction temperature of this reaction is usually - 50 to 150°C, preferably -20 to 100°C, more preferably -10 to 50°C.
  • the reaction time is usually 0.1 to 96 hours, preferably 0.1 to 24 hours.
  • the compound of the present invention can be isolated by concentrating the reaction mixture; or by pouring the reaction mixture into water, then, extracting with an organic solvent, and performing usual post-treatment operations such as concentration.
  • the resultant compound of the present invention can be purified by conventional methods, for example, distillation, re-precipitation, re- crystallization, or chromatography, in some cases.
  • the compound (II) is a known compound.
  • A is a phenyl group optionally substituted with (X 2 ) q , namely the compound of the formula:
  • the compound (II) can be produced from the compound of the formula (IV-I) :
  • Si a represents a trialkylsilyl such as trimethylsilyl, or triethylsilyl
  • X 2 , X 3 , q and r respectively represent the same meanings as described above .
  • the compound (IV-I) is a known compound, or it can be produced by known methods, for example, a method described in J. Org. Chem, 1981, 46, 2280-2286, or J. Am. Chem. Soc, 2006, 128(14), 4592-4593.
  • the compound (III) is a known compound, or it can be produced by known methods .
  • the amount of the compound (III) may be a large excess amount, and preferably 0.8 to 5 equivalents, more preferably 0.7 to 1.2 equivalents to the compound (IV) .
  • a base or an acid may be present in the reaction system, if necessary.
  • Such a base includes for example, alkali metal alcoholates such as sodium ethylate, sodium methylate, or potassium tert-butoxide; nitrogen-containing organic compounds such as triethylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, or N,N-dimethylaniline; carbonates such as potassium carbonate, sodium carbonate, sodium hydrogen carbonate, or potassium hydrogen carbonate; hydroxides such as sodium hydroxide, or potassium hydroxide; metal hydrides such as lithium hydride, sodium hydride, or potassium hydride; and organolithiums such as butyllithium, or lithiumdiisopropylamide .
  • the amount of the base to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and preferably 0.01 to 0.5 equivalents, more preferably 0.01 to 0.2 equivalents to the compound (IV) .
  • Such an acid includes, for example, mineral acids such as hydrochloric acid, sulfuric acid, or nitric acid; organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, methanesulfonic acid, benzenesulfonic acid, or p-toluenesulfonic acid; acid addition salts of amines such as triethylamine hydrochloride, or pyridine hydrochloride; and Lewis acids such as aluminum chloride, zinc chloride, zinc iodide, titanium tetrachloride, cerium chloride, ytterbium triflate, or boron trifluoride-ether complex.
  • mineral acids such as hydrochloric acid, sulfuric acid, or nitric acid
  • organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, methanesulfonic acid, benzenesulfonic acid, or p-toluenes
  • the amount of the acid to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and preferably 0.01 to 0.5 equivalents, more preferably 0.01 to 0.2 equivalents to the compound (IV) .
  • the reaction of the step (2-1) can be carried out in the presence of a suitable solvent .
  • Such a solvent examples include alcohols such as methanol, ethanol, or isopropanol; aliphatic hydrocarbons such as pentane, hexane, heptane, or petroleum ether; aromatic hydrocarbons such as benzene, toluene, or xylene; esters such as methyl acetate, ethyl acetate, ethyl formate, or ethyl propionate; ketones such as acetone, or methylethylketone; ethers such as diethylether, dipropylether, diisopropylether, dibutylether, tetrahydrofuran, or dioxane; nitriles such as acetonitrile, or propionitrile; acid amides such as dimethylformamide, or dimethylacetamide; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; phosphoric amide
  • the reaction temperature of the step (2-1) is usually -50 to 150°C, preferably -20 to 100°C, more preferably -10 to 5O 0 C.
  • the reaction time is usually 0.1 to 96 hours, preferably 0.1 to 24 hours.
  • the de-trialkylsilylation reaction can be carried out by allowing a base to act on the compound (V) .
  • the reaction of the step (2-2) can be carried out in the presence of a suitable solvent.
  • a suitable solvent include the same solvents as in the step (2-1) . These solvents may be used in admixture, and may also be used as a mixed solvent with water.
  • the same bases as in the step (2-1) are mentioned.
  • the amount of the base to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and preferably 0.01 to 5 equivalents, more preferably 0.1 to 1.5 equivalents to the compound (IV) .
  • the reaction temperature of the step (2-2) is usually -20 to 150°C, preferably 0 to 120°C, more preferably 10 to 80°C.
  • the reaction time is usually 0.1 to 96 hours, preferably 0.1 to 24 hours .
  • the compound of the present invention can be isolated by concentrating the reaction mixture; or by pouring the reaction mixture into water, extracting with an organic solvent, then, performing usual post-treatment operations such as concentration.
  • the resultant compound of the present invention can be purified by conventional methods, for example, distillation, re-precipitation, re- crystallization, or chromatography.
  • the compound of the present invention can be produced also by confirming production of the compound (V) in the step (2-1) , then, performing the de-trialkylsilylation reaction of the step (2-2) without isolation and purification of the compound (V) .
  • a compound in which A represents a phenyl group optionally substituted with (X 2 ) q or an aromatic hetero ring optionally substituted with a Cl to C5 alkyl group or a halogen atom can be produced, for example, by the following production method.
  • the production method comprises a step (3-1) of reacting the compound of the formula (hereinafter described as compound (VI) ) :
  • A represents a phenyl group optionally substituted with (X 2 ) q or an aromatic hetero ring optionally substituted with a Cl to C5 alkyl group or a halogen atom
  • R represents a hydrogen atom or a Cl to C5 alkyl group optionally substituted with a halogen atom
  • X 1 , X 3 , p and r represent the same meanings as described above.
  • X represents a halogen atom.)/ and a step (3-4) of de-halogenating the compound (X) to obtain the compound of the present invention.
  • the amount of the compound (III) may be a large excess amount, and preferably 0.8 to 5 equivalents, more preferably 0.7 to 1.2 equivalents to the compound (VI) .
  • a base or an acid may be present in the reaction system, if necessary.
  • a base or acid for example, the same bases and acids as in the step (2-1) are mentioned.
  • the amount of the base to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and preferably 0.01 to 0.5 equivalents, more preferably 0.01 to 0.2 equivalents to the compound (VI).
  • the amount of the acid to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and preferably 0.01 to 0.5 equivalents, more preferably 0.01 to 0.2 equivalents to the compound (VI ) .
  • the reaction of the step (3-1) can be carried out in the presence of a suitable solvent.
  • a suitable solvent for example, the same solvents as in the step (2-1) are mentioned. These solvents may be used in admixture, or as a mixed solvent with water.
  • the reaction temperature of the step (3-1) is usually -50 to 150 0 C, preferably -20 to 100 0 C, more preferably -10 to 50 0 C.
  • the reaction time is usually 0.1 to 96 hours, preferably 0.1 to 24 hours.
  • the compound (VII) can be isolated by concentrating the reaction mixture; or by pouring the reaction mixture into water, extracting with an organic solvent, then, performing usual post-treatment operations such as concentration.
  • the resultant compound (VII) can be purified by conventional methods, for example, distillation, re-precipitation, re- crystallization, or chromatography.
  • the compound (VI) is a known compound, or it can be produced by known methods, for example, a method described in J. Chem. Soc . Perkin Trans. 1, 1793 .1988, Synthesis 1984, 339-345, and other methods.
  • the amount of the compound (VIII) may be a large excess amount, and preferably 0.8 to 5 equivalents, more preferably 0.7 to 1.2 equivalents to the compound (VII) .
  • the reaction of the step (3-2) can be carried out in the presence of a suitable solvent.
  • a suitable solvent include the same solvents as in the step (2-1) . These solvents can also be used in admixture.
  • the method for removing water includes a method of removing water out of the reaction system by azeotropic distillation with a solvent, and a method of adding a dehydrating agent such as molecular sieve into the reaction system.
  • the presence of a catalyst is not essential, however, the reaction is accelerated by addition of an acid or base, in some cases.
  • the acid may be an organic acid or an inorganic acid.
  • the organic acid include formic acid, acetic acid and propionic acid, and these can be used also as a solvent.
  • the inorganic acid include hydrochloric acid, sulfuric acid, methanesulfonic acid, benzenesulfonic acid, P-toluenesulfonic acid, and Lewis acids such as cerium chloride, aluminum chloride, zinc chloride, titanium tetrachloride, or boron trifluoride- diethylether complex. Of them, sulfuric acid, polyphosphates and the like can be used as both a solvent and as a dehydrating agent. Examples of such a base include inorganic bases such as potassium hydroxide, sodium hydroxide, or sodium methoxide and organic bases such as pyridine, or triethylamine, and of them, organic bases can be used also as a solvent .
  • the reaction temperature of the step (3-2) is usually 0 to 200 0 C, preferably 20 to 150°C, more preferably 30 to 100°C.
  • the reaction time is usually 0.1 to 96 hours, preferably 0.1 to 24 hours.
  • the compound (IX) can be isolated by concentrating the reaction mixture; or by pouring the reaction mixture into water, extracting with an organic solvent, then, performing usual post-treatment operations such as concentration.
  • the resultant compound (IX) can be purified by conventional methods, for example, distillation, re-precipitation, re- crystallization or chromatography.
  • halogenating agent includes chlorine, bromine, iodine, thionyl chloride, thionyl bromide, N-chlorosuccinimide, N-bromosuccinimide and N-iodosuccinimide.
  • the amount of the halogenating agent to be used is usually 0.7 to 2.0 equivalents, preferably 0.8 to 1.5 equivalents to the compound (IX).
  • the reaction of the step (3-3) can be carried out in the presence of a suitable solvent .
  • a suitable solvent include the same solvents as in the step (2-1) . These solvents may be used in admixture, or may be used also as a mixed solvent with water.
  • the reaction temperature of the step (3-3) is usually -50 to 150 0 C, preferably -20 to 100°C, more preferably -10 to 50°C.
  • the reaction time is usually 0.1 to 96 hours, preferably 0.1 to 24 hours.
  • the compound (X) can be isolated by concentrating the reaction mixture; or by pouring the reaction mixture into water, extracting with an organic solvent, then, performing usual post-treatment operations such as concentration.
  • the resultant compound (X) can be purified by conventional methods, for example, distillation, re-precipitation, re- crystallization or chromatography.
  • a compound (I) can be produced by allowing a base to act on the compound (X) .
  • Examples of such a base include alkali metal alcoholates such as sodium ethylate, sodium methylate, or potassium tert-butoxide; nitrogen-containing organic compounds such as triethylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, or N, N-dimethylaniline ; carbonates such as potassium carbonate, sodium carbonate, sodium hydrogen carbonate, or potassium hydrogen carbonate; hydroxides such as sodium hydroxide, or potassium hydroxide; metal hydrides such as lithium hydride, sodium hydride, or potassium hydride; and organolithiums such as butyllithium, or lithiumdiisopropylamide .
  • the amount of the base to be used is not particularly restricted providing it does not exert a reverse influence on the reaction, and it is preferably 0.5 to 5 equivalents, more preferably 0.8 to 2.0 equivalents to the compound (X) .
  • the reaction of the step (3-4) can be carried out in the presence of a suitable solvent .
  • a suitable solvent include the same solvents as in the step (2-1) . These solvents may be used in admixture, or may be used also as a mixed solvent with water.
  • the reaction temperature of the step (3-4) is usually -50 to 150°C, preferably -20 to 100 0 C, more preferably -10 to 50 0 C.
  • the reaction time is usually 0.1 to 96 hours, preferably 0.1 to 24 hours.
  • the compound of the present invention can be isolated by concentrating the reaction mixture; or by pouring the reaction mixture into water, extracting with an organic solvent, then, performing usual post-treatment operations such as concentration.
  • the resultant compound of the present invention can be purified by conventional methods, for example, distillation, re-precipitation, re- crystallization or chromatography.
  • the compound of the present invention may exist as various isomers including geometric isomers and stereoisomers. All isomers of the compound of the present invention and a mixture of the isomers are indluded in the scope of the present invention.
  • the compound of the present invention has an excellent controlling effect on pests including hygiene pests, animal parasitic pests and plant parasitic pests, and thus it is effective for pest control.
  • the compound of the present invention exerts an excellent controlling effect on pests when the compound is applied directly to the pests or to places where the pests inhabit.
  • a pesticidal composition comprising as an active ingredient the compound of the present invention falls within the scope of the present invention.
  • the compound of the present invention When the compound of the present invention is used as a composition for pest control, that is, the pesticidal composition, the compound of the present invention may be used as it is. However, the compound of the present invention is usually formulated into forms which usual agrichemicals or animal drugs may take, and then used. In other words, the pesticidal composition of the present invention may be the compound of the present invention itself, and however, it usually comprises the compound of the present invention and additives to take a suitable form for usual agrichemicals or animal drugs.
  • the compound of the present invention is dissolved or dispersed in a suitable liquid carrier, mixed with a suitable solid carrier and/or a suitable gaseous carrier, or adsorbed on a suitable solid carrier to prepare the pesticidal composition of the present invention in the form of an emulsifiable concentrate, a liquid formulation, a microemulsion, a flowable formulation, an oil solution, a wettable powder, a dust, a granule, a microgranule, a seed- coating agent, a seed-immersion solution, a smoking pesticide, a tablet, a microcapsule, a spray, an aerosol, a carbon dioxide gas formulation, a heating fumigant such as a mosquito coil, an electric mosquito mat or an electric mosquito liquid, EW formulation, an ointment, a poison bait, a capsule, a pellet, a film, an injectable, a liniment, a resin formulation, a shampoo formulation or the like.
  • a suitable liquid carrier mixed with a suitable solid
  • the pesticidal composition of the present invention may further contain an emulsifier, a suspending agent, a spreading agent, a penetrating agent, a wetting agent, a thickener, a stabilizer, a dispersant or the like.
  • the pesticidal composition of the present invention can be prepared by a known method.
  • liquid carrier examples include water, alcohols (e.g., methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, butyl alcohol, hexyl alcohol, benzyl alcohol, ethylene glycol, propylene glycol, or phenoxyethanol) , ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone) , ethers (e.g., diisopropyl ether, 1, 4-dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, or 3-methoxy-3-methyl- 1-butanol) , aliphatic hydrocarbons (e.g., hexane
  • the solid carrier e.g., a diluent or a filler
  • vegetable powders e.g., soybeen powder, tobacco powder, flour, or wood powder
  • mineral powders e.g., kaolin, Fubasami, bentonite, clay such as acid clay, talc such as talcum powder or agalmatolite powder, diatomaceous earth, silica such as mica powder
  • chemical fertilizers e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, or urea
  • alumina sulfur powder, activated carbon, calcium carbonate, potassium chloride, sodium hydrogen carbonate, and lactose.
  • These solid carriers may be used alone, or two or more, preferably one to three of these solid carriers may be mixed in appropriate proportion
  • gaseous carrier examples include fluorocarbon, butane gas, LPG (liquefied petroleum gas) , dimethyl ether, and carbon dioxide gas . These gaseous carriers may be used alone, or two or more of these gaseous carriers may be mixed in appropriate proportions and then used. Alternatively, one or more of these gaseous carriers may be used in combination with a suitable liquid carrier.
  • examples of a base material for the ointment include polyethylen glycol, pectin, esters of higher fatty acid and polyalcohol such as glyceryl monostearate ester, cellulose derivatives such as methylcellulose, sodium alginate, bentonite, higher alcohol, polyalcohol such as glycerin, petrolatum, white petrolatum, liquid paraffin, lard, vegetable oils, lanolin, anhydrous lanoiln, hydrogenated oils, and resin.
  • These base materials may be used alone, or two or more, preferably one to three of these base materials may be used in combination. Further, a surfactant as listed below may be added to the base material .
  • a surfactant may be used as an emulsifier, a spreading agent, a penetrating agent, a dispersant or the like in preparing the pesticidal composition of the present invention.
  • the surfactant include soap; and nonionic and anionic surfactants such as polyoxyethylene alkyl aryl ether [NOIGEN (trade name) , E A142 (trade name) manufactured by DAI-ICHI KOGYO SEIYAKU CO., LTD.; NONAL (trade name) manufactured by TOHO CHEMICAL INDUSTRY CO., LTD.], alkyl sulfate [e.g.
  • EMAL 10 (trade name) and EMAL 40 (trade name) manufactured by KAO CORPORATION]
  • alkylbenzene sulfonate e.g. NEOGEN (trade name) and NEOGEN T (trade name) manufactured by DAI-ICHI KOGYOU SEIYAKU CO., LTD.
  • NEIPELEX (trade name) manufactured by KAO CORPORATION]
  • polyethylene glycol ether e.g., NONIPOL 85 (trade name), NONIPOL 100 (trade name) , and NONIPOL 160 (trade name) manufactured by SANYO KASEI
  • polyoxyethylene alkyl ether e.g.
  • NOIGEN ET-135 (trade name) manufactured by DAI-ICHI KOGYO SEIYAKU CO., LTD.] polyoxyethylene polyoxypropylene block polymer [e.g. NEWPOLE PE- 64 (trade name) manufactured by SANYO CHEMICAL INDUSTRIES LTD.], polyalcohol ester [e.g. TWEEN 20 (trade name) and TWEEN 80 (trade name) manufactured by KAO CORPORATION] , alkyl sulfosuccinate [e.g.
  • SANMOLIN OT20 (trade name) manufactured by SANYO CHEMICAL INDUSTRIES LTD.; NEWKALGEN EX70 (trade name) manufactured by TAKEMOTO OIL & FAT CO., LTD.], alkyl naphthalenesulfonate [NEWKALGEN WG-I (trade name) manufactured by TAKEMOTO OIL & FAT CO., LTD.], and alkenyl naphthalenesulfonate [SORPOL 5115 (trade name) manufactured by TOHO CHEMICAL INDUSTRY CO., LTD.].
  • These surfactants may be used alone, or two or more, preferably one to three of these surfactants may be mixed in appropriate proportions and then used.
  • Examples of a base material for the resin formulation include vinyl chloride polymers, and polyurethane .
  • a plasticizer such as phthalate (e.g., dimethyl phthalate, dioctyl phthalate, etc.), adipate, stearic acid or the like may be added.
  • the resin formulation is prepared by kneading the compound of the present invention into the base material using a conventional kneader, followed by molding such as injection molding, extrusion molding, press molding or the like.
  • the resulting resin formulation may be formed into the shape of a plate, a film, a tape, a net, a string or the like via a further step of molding, cutting, or the like, if necessary.
  • These resin formulations may be used, for example, the form of an animal collar, an animal ear tag, a sheet, a lead, or a horticultural post.
  • Examples of a base material of the poison bait include cereal powder, vegetable oil, sugar, and crystalline cellulose.
  • an antioxidant such as dibutylhydroxytoluene or nordihydroguaiaretic acid, a preservative such as dehydroacetic acid, an agent for preventing children or pets from erroneously eating such as hot pepper powder, a pest-attractive perfume such as cheese perfume, onion perfume or peanut oil or the like may be added.
  • a binder e.g., a dispersant, a colorant, a stabilizer and the like, specifically, casein, gelatin, saccharides (e.g., starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (e.g., polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acid, etc.), PAP (acid isopropyl phosphate), BHT (2, 6-di-tert- butyl-4-methylphenol) , BHA (a mixture of 2-tert-butyl-4- methoxyphenol and 3-tert-butyl-4-methoxyphenol) , other substances described in Code of Federal Regulation Title 40 p.180, USA can be used as pharmaceutical auxiliary agents for preparing the pesticidal composition of the present invention.
  • saccharides e.g., starch, gum arabic, cellulose derivatives, alginic acid,
  • the pesticidal composition of the present invention can comprise the compound of the present invention in combination with another pesticidal active ingredient, such as an insecticide (e.g., pyrethroid insecticide, organic phosphorus insecticide, carbamate insecticide, neonicotinoid insecticide, nerve sodium channel blocker, insecticidal macrocyclic lactone, ⁇ -amino butyric acid (GABA) antagonisy, calcium channel activater, urea insecticide, insect hormone mimic, natural insecticide, etc.), an acaricide, a machine oil, a nematocide, a herbicide, a phytohormone agent, a plant growth regulator, a fungicide (e.g., copper fungicide, organic chlorine fungicide, organic sulfur fungicide, phenol fungicide, etc.), a synergist, an attractant, a repellent, a crop injury-reducing agent, a pigment, a fertilizer, an animal feed (e.g., feed for livestock such as cows,
  • the pesticidal composition of the present invention contains usually 0.1 to 80% by weight, preferably 1 to 20% by weight of the compound of the present invention.
  • the pesticidal composition of the present invention when it is in the form of an emulsifiable concentrate, a liquid formulation or a wettable powder (e.g., a wetabble granule), it contains usually 1 to 80% by weight, preferably 1 to 20% by weight of the compound of the present invention.
  • the pesticidal composition of the present invention is in the form of an emulsifiable concentrate or a dust, it cntains usually 0.1 to 50% by weight, preferably 0.1 to 20% by weight of the compound of the present invention.
  • the pesticidal composition of the present invention When the pesticidal composition of the present invention is in the form of a granule, it contains usually 1 to 50% by weight, preferably 1 to 20% by weight of the compound of the present invention.
  • Another pesticidal active ingredient e.g., insecticide, herbicide, an acaricide, fungicide, etc.
  • insecticide, herbicide, an acaricide, fungicide, etc. may be present in usually 0.1 to 80% by weight, preferably 1 to 20% by weight in the pesticidal composition of the present invention.
  • the content of additives other than the pesticidal active ingredient described above in the pesticidal composition of the present invention is usually 0.001 to 99.9% by weight, preferably 1 to 99% by weight, although it is varied depending on the kind and content of the pesticidal active ingredient, the form of the pesticidal composition and the like.
  • the content of a surfactant in the pesticidal composition of the present invention is usually 1 to 20% by weight, preferably 1 to 15% by weight.
  • the content of a fluidizing aid in the pesticidal composition of the present invention is usually 1 to 20% by weight.
  • the content of a carrier in the pesticidal composition of the present invention is usually 1 to 90% by weight, preferably 1 to 70% by weight.
  • the pesticidal composition of the present invention is in the form of an emulsifiable concentrate or a wettable powder (e.g., a wetabble granule), it is preferably diluted with water or the like as appropriate (e.g., 100 to 5,000 times) and then sprayed.
  • a wettable powder e.g., a wetabble granule
  • the compound of the present invention can be used as an insecticide for crop lands such as cultivated lands, paddy fields, lawns and orchards, or non-crop lands.
  • the compound of the present invention can control pests in crop lands and the like where "crop plants” listed below are cultivated without causing adverse effects on the "crop plants", in some cases.
  • Agricultural crops corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, sarrazin, sugar beet, rapeseed, sunflower, sugar cane, tobacco, etc.;
  • Vegetables Solanaceae vegetables (eggplant, tomato, green pepper, hot pepper, potato etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon etc.), Cruciferae vegetables (Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, cauliflower etc.), Compositae vegetables (burdock, garland chrysanthemum, artichoke, lettuce etc.), Liliaceae vegetables (Welsh onion, onion, garlic, asparagus etc.), Umbelliferae vegetables (carrot, parsley, celery, parsnip etc.), Chenopodiaceae vegetables (spinach, Swiss chard etc.), Labiatae vegetables (Japanese basil, mint, basil etc.), strawberry, sweat potato, yam, aroid, etc.;
  • Fruit trees pomaceous fruits (apple, common pear, Japanese pear, Chinese quince, quince etc.), stone fleshy fruits (peach, plum, nectarine, Japanese plum, cherry, apricot, prune etc.)/ citrus plants (Satsuma mandarin, orange, lemon, lime, grapefruit etc.), nuts (chestnut, walnut, hazel nut, almond, pistachio, cashew nut, macadamia nut etc.), berry fruits (blueberry, cranberry, blackberry, raspberry etc.), grape, persimmon, olive, loquat, banana, coffee, date, coconut palm, oil palm, etc.;
  • Trees other than fruit trees tea, mulberry, street trees (ash tree, birch, dogwood, eucalyptus, ginkgo, lilac, maple tree, oak, poplar, cercis, Chinese sweet gum, plane tree, zelkova, Japanese arborvitae, fir tree, Japanese hemlock, needle juniper, pine, spruce, yew, elm, horse- chestnut etc.), sweet viburnum, Podocarpus macrophyllus, Japanese cedar, Japanese cypress, croton, spindle tree, Chainese howthorn, etc.
  • Oil crops oil palm, Barbados nut, etc.;
  • flowers (rose, carnation, chrysanthemum, ⁇ ustoma grandiflorum Shinners (prairie gentian) , gypsophila, gerbera, pot marigold, salvia, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid, lily of the valley, lavender, stock, ornamental kale, primula, poinsttia, gladiolus, cattleya, daisy, verbena, cymbidium, begonia, etc.), foliage plant; etc..
  • the above-described crop plants include those to which resistance to an HPPD inhibitor such as isoxaflutole, an ALS inhibitor such as imazethapyr or thifensulfuron-methyl , an EPSP synthesizing enzyme inhibitor such as glyphosate, a glutamine synthesizing enzyme inhibitor such as glufosinate, an acetyl CoA carboxylase inhibitor such as sethoxydim, a PPO inhibitor such as flumioxazin, or an herbicide such as bromoxynil, dicamba or 2, 4-D, has been imparted by a classical breeding method or a genetic engineering technique.
  • HPPD inhibitor such as isoxaflutole
  • an ALS inhibitor such as imazethapyr or thifensulfuron-methyl
  • an EPSP synthesizing enzyme inhibitor such as glyphosate
  • glutamine synthesizing enzyme inhibitor such as glufosinate
  • an acetyl CoA carboxylase inhibitor such as seth
  • Examples of the crop plant to which the resistance has been imparted by a classical breeding method include rape, whieat, sunflower, rice and corn having resistance to imidazolinone herbicides such as imazethapyr, which are commercially available under the trade name of Clearfield (registered trademark) ; soybean having resistance to sulfonylurea ALS inhibitor herbicides such as thifensulfuron-methyl, which is commercially available under the trade name of STS soybean; and crop plants having resistance to acetyl CoA carboxylase inhibitors such as trione oxime hebicides and aryloxyphenoxypropionic acid herbicides, an example of which is SR corn.
  • a crop plant resistant to an acetyl CoA carboxylase inhibitor can be produced.
  • nucleic acids for introduction of a base substitution mutation can be introduced into the cells of a crop plant by chimeraplasty (see, Gura T.
  • Examples of the crop plant to which the resistance has been imparted by a genetic engineering technique include corn, soybean, cotton, rape and sugar beet cultivars which are resistant to glyphosate, which are commercially available under the trade names of RoundupReadyTM (registered trademark) , AgrisureGT, and the like.
  • Other examples of the crop plant to which the resistance has been imparted by a genetic engineering technique include corn, soybean, cotton and rape cultivars which are resistant to glufosinate, which are commercially available under the trade name of LibertyLinkTM and the like.
  • a genetically engineered cotton cultivar having resisitance to bromoxynil is commarcially available under the trade name of BXN.
  • the above-described crop plants include those to which ability to produce an insecticidal toxin, for example a selective toxin which is known to be produced by Bacillus, has been imparted by a genetic engineering technique.
  • insecticidal toxin which is produced by such a genetically engineered plant
  • insecticidal proteins derived from Bacillus cereus and Bacillus popilliae include insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; ⁇ -endotoxins derived from Bacillus thuringiensis, such as CryIAb, CryIAc, CrylF, CrylFa2 , Cry2Ab, Cry3A, Cry3Bbl and Cry9C; insecticidal proteins derived from Bacillus thuringiensis, such as VIP 1, VIP 2, VIP 3 and VIP 3A; insecticidal proteins derived from nematodes / toxins produced by animals such as scorpion toxins, spider toxins, bee toxins and insect-specific nerve toxins; fungal toxins,- plant lectin; agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin,
  • the insecticidal toxin which is produced by such a genetically engineered plant also includes hybrid toxins of different insecticidal proteins, for example, insecticidal proteins such as ⁇ -endotoxins such as CryIAb, CryIAc, CrylF, CrylFa2 , Cry2Ab, Cry3A, Cry3Ebl and Cry9C, VIP 1, VIP 2, VIP 3 and VIP 3A, and toxins in which a part of amino acids constituting an insecticidal protein is deleted or modified.
  • the hybrid toxin is made by combining different domains of the insecticidal proteins by a genetic engineering technique.
  • An example of the toxin in which a part of amino acids constituting an insecticidal protein is deleted includes CrylAb in which a part of amino acids is deleted.
  • An example of the toxin in which a part of amino acids constituting an insecticidal protein is modified includes a toxin in which one or more of amino acids of a naturally occurring toxin are substituted.
  • insecticidal toxin and the genetically engineered crop plant having the ability to produce the insecticidal toxin are described, for example, in EP-A-O 374 753, WO 93/07278, WO 95/34656, EP-A-O 427 529, EP-A-451878, WO 03/052073, and the like.
  • the genetically engineered crop plant having the ability to produce the insecticidal toxin particularly has resistance to attack by a coleopteran pest, dipteran pest or a lepidopteran pest .
  • Genetically engineered plants which have one or more pest-resistance genes and thereby produce one or more insecticidal toxins are also known, and some of them are commercially available.
  • Examples of such genetically engineered plants include YieldGardTM (a corn cultivar expressing CrylAb toxin) , YieldGard RootwormTM (a corn cultivar expressing Cry3Bbl toxin) , YieldGard PlusTM (a corn cultivar expressing CrylAb and Cry3Bbl toxins) , Herculex ITM (a corn cultivar expressing CrylFa2 toxin and phosphinothricin N-acetyltransferase (PAT) for imparting resistance to gluphosinate) , NuCOTN33BTM (a cotton cultivar expressing CrylAc toxin) , Bollgard ITM (a cotton cultivar expressing CrylAc toxin) , Bollgard IITM (a cotton cultivar expressing CrylAc and Cry2Ab toxins
  • the above-described crop plants include those to which ability to produce an anti -pathogen substance has been imparted by a genetic engineering technique.
  • anti-pathogen substance examples include PR proteins (PRPs described in EP-A-O 392 225) ; ion channel inhibitors such as sodium channel inhibitors, and calcium channel inhibitors (e.g. KPl, KP4 , KP6 toxins etc. produced by viruses) ; stilbene synthase; bibenzyl synthase; chitinase; glucanase; substances produced by microorganisms such as peptide antibiotics, heterocycle-containing antibiotics, and protein factors involved in plant disease- resistance (described in WO 03/000906) ; and the like.
  • PR proteins PRPs described in EP-A-O 392 225
  • ion channel inhibitors such as sodium channel inhibitors, and calcium channel inhibitors
  • stilbene synthase e.g. KPl, KP4 , KP6 toxins etc. produced by viruses
  • stilbene synthase e.g. KPl, KP4 , KP6 toxins etc. produced by viruses
  • the above-described crop plants include those to which a beneficial character such as a modified oil component or an enhanced amino acid content has been imparted by a genetic engineering technique.
  • a beneficial character such as a modified oil component or an enhanced amino acid content
  • crop paints include VISTIVETM (low linolenic soybean which has a reduced content of linolenic acid)
  • high-lysine high- oil corn (corn which has an increased content of lysine or oil) .
  • the above-described crop plants include stacked plants which have a combination of two or more of beneficial characters such as the above-described classical harbicide-resistant character, or a herbicide-resistace gene, a pest-resistance gene, an anti-pathogen substance- producing gene, a modified oil component, and an enhanced amino acid content .
  • beneficial characters such as the above-described classical harbicide-resistant character, or a herbicide-resistace gene, a pest-resistance gene, an anti-pathogen substance- producing gene, a modified oil component, and an enhanced amino acid content .
  • the plant is treated with sequentially or a mixture of the compound of the present invention and the herbicide (e.g., glyphosate or a salt thereof, glufosinate or a salt thereof, dicamba or a salt thereof, imazethapyr or a salt thereof, isoxaflutole, etc.) to which the plant is resistant, and thereby comprehensive weed control can be attained.
  • the herbicide e.g., glyphosate or a salt thereof, glufosinate or a salt thereof, dicamba or a salt thereof, imazethapyr or a salt thereof, isoxaflutole, etc.
  • the active ingredient group X examples of active ingredients of insecticides, acaricides, nematocides, fungicides, herbicides, phytohormone agents, plant growth regulators, synergists and crop injury-reducing agents (hereinafter, referred to as "the active ingredient group X") which can be used in combination with the compound of the present invention are listed below.
  • active ingredients of the insecticides include :
  • organic phosphorus compounds acephate, aluminum phosphide, butathiofos, cadusafos, chlorethoxyfos, chlorfenvinphos, chlorpyrifos, chlorpyrifos-methyl, cyanophos (CYAP), diazinon, DCIP
  • PAP profenofos, propaphos, prothiofos, pyraclorfos, salithion, sulprofos, tebupirimfos, temephos, tetrachlorvinphos, terbufos, thiometon, trichlorphon (DEP) , vamidothion, phorate, cadusafos, and the like;
  • carbamate compounds alanycarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenobucarb, fenothiocarb, fenoxycarb, furathiocarb, isoprocarb (MIPC), metolcarb, methotnyl, methiocarb, NAC, oxamyl, pirimicarb, propoxur (PHC), XMC, thiodicarb, xylylcarb, aldicarb, and the like;
  • nereistoxin compounds cartap, bensultap, thiocyclam, monosultap, bisultap, and the like;
  • neonicotinoid compounds imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, clothianidin, and the like;
  • benzoylurea compounds chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triazuron, and the like;
  • phenylpyrazole compounds acetoprole, ethiprole, fipronil, vaniliprole, pyriprole, pyrafluprole, and the like;
  • Bt toxin insecticides live spores derived from and crystal toxins produced from Bacillus thuringiesis and a mixture thereof;
  • hydrazine compounds chromafenozide, halofenozide, methoxyfenozide, tebufenozide, and the like;
  • organic chlorine compounds aldrin, dieldrin, dienochlor, endosulfan, methoxychlor, and the like;
  • insecticides avermectin, bromopropylate, buprofezin, chlorphenapyr, cyromazine, D-D (1, 3-dichloropropene) , emamectin-benzoate, fenazaquin, flupyrazofos, hydroprene, methoprene, indoxacarb, metoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, flubendiamide, lepimectin, arsenic acid, benclothiaz, calcium cyanamide, calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formetanate, metham-ammonium, metam-sodium, methyl bromide, potassium oleate,
  • X al represents a methyl group, a chlorine atom, a bromine atom or a fluorine atom
  • X a2 represents a fluorine atom, a chlorine atom, a bromine atom, a C1-C4 haloalkyl grop or a C1-C4 haloalkoxy group
  • X a3 represents a fluorine atom, a chlorine atom or a bromine atom
  • X a4 represents an optionally substituted C1-C4 alkyl group, an optionally substituted C3-C4 alkenyl group , an optionally substituted C3-C4 alkynyl group, an optionally substituted C3-C5 cycloalkylalkyl group or a hydrogen atom
  • X a5 represents a hydrogen atom or a methyl group
  • X a6 represents a hydrogen atom, a fluorine atom or a chlorine atom
  • X a7
  • X b2 represents an optionally substituted C1-C4 haloalkyl group, such as a 2 , 2 , 2-trifluoroethyl group, or an optionally substituted C3-C6 cycloalkyl group, such as a cyclopropyl group
  • X b3 represents an optionally substituted C1-C4 alkyl group, such as a methyl group
  • X b4 represents a hydrogen atom, a cyano group or
  • X cl represents an optionally substituted C1-C4 alkyl group, such as a 3 , 3 , 3-trifluoropropyl group, an optionally substituted C1-C4 alkoxy group, such as a 2,2,2- trichloroethoxy group, an optionally substituted phenyl group, such as a 4-cyanophenyl group, or an optionally substituted pyridyl group, such as a 2-chloro-3-pyridyl group, X c2 represents a methyl group or a trifluoromethylthio group, and X 03 represents a methyl group or a halogen atom; and the like.
  • C1-C4 alkyl group such as a 3 , 3 , 3-trifluoropropyl group
  • an optionally substituted C1-C4 alkoxy group such as a 2,2,2- trichloroethoxy group
  • an optionally substituted phenyl group such as a 4-cyanoph
  • active ingredients of the acaricides include acequinocyl, amitraz, benzoximate, bifenazate, bromopropylate, chinomethionate, chlorobenzilate, CPCBS (chlorfenson) , clofentezine, cyflumetofen, kelthane (dicofol) , etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, fluproxyfen, hexythiazox, propargite (BPPS), polynactins, pyridaben, pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, spirotetramat , amidoflumet, cyenopyrafen, and the like.
  • active ingredients of the nematicides include DCIP, fosthiazate, levamisol hydrochloride, methylisothiocyanate, morantel tartarate, imicyafos .
  • active ingredients of the fungicides include azole fungicidal compounds such as propiconazole, prothioconazole, triadimenol, prochloraz, penconaz ⁇ le, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole, myclobutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanol, imazalil, and flutriafol; cyclic amine fungicidal compouds such as fenpropimorph, tridemorph, and fenpropidin; benzimidazole fungicidal compounds such as carbendezim, benomyl, thiabendazole, and thiophanate-methyl-
  • active ingredients of the herbicides and the phytohormone agents include:
  • phenoxyfatty acid herbicidal compounds such as 2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, and naproanilide;
  • benzoic acid herbicidal compounds such as 2,3,6- TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac;
  • urea herbicidal compounds such as diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, methabenzthiazuron, cumyluron, daimuron, and methyl-daimuron;
  • triazine herbicidal compounds such as atrazine, ametoryn, cyanazine, simazine, propazine, simetryn, dimethametryn, prometryn, metribuzin, and triaziflam;
  • bipyridinium herbicidal compounds such as paraquat , and diquat ;
  • dinitroaniline herbicidal compounds such as pendimethalin, prodiamine, and trifluralin;
  • organic phosphorus herbicidal compounds such as amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, and bialaphos;
  • carbamate herbicidal compounds such as di-allate, tri-allate, EPTC, butylate, benthiocarb, esprocarb, molinate, dimepiperate, swep, chlorpropham, phenmedipham, phenisopham, pyributicarb, and asulam;
  • acid amide herbicidal compounds such as propanil, propyzamide, bromobutide, and etobenzanid
  • chloroacetanilide herbicidal compounds such as acetochlor, alachlor, butachlor, dimethenamid, propachlor, metazachlor, metolachlor, pretilachlor, thenylchlor, and pethoxamid;
  • diphenylether herbicidal compounds such as acifluorfen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, chlomethoxynil, and aclonifen;
  • cyclic imide herbicidal compounds such as oxadiazon, cinidon-ethyl , carfentrazone-ethyl, surfentrazone, flumiclorac-pentyl , flumioxazin, pyraflufen- ethyl, oxadiargyl, pentoxazone, fluthiacet-methyl, butafenacil, and benzfendizone;
  • pyrazole herbicidal compounds such as benzofenap, pyrazolate, pyrazoxyfen, topramezone, and pyrasulfotole;
  • triketone herbicidal compounds such as isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefuryltrione;
  • aryloxyphenoxypropionic acid herbicidal compounds such as clodinafop-propargyl, cyhalofop-butyl, diclofop- methyl , fenoxaprop-ethyl, fluazifop-butyl, haloxyfop- methyl , and quizalofop-ethyl ;
  • trioneoxime herbicidal compounds such as alloxydim-sodium, sethoxydim, butroxydim, clethodim, cloproxydim, cycloxydim, tepraloxydim, tralkoxydim, and profoxydim;
  • sulfonylurea herbicidal compounds such as chlorsulfuron, sulfometuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron-methyl, triasulfuron, bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron- ethyl, primisulfuron-methyl , nicosulfuron, amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron- methyl, prosulfuron, ethametsulfuron-methyl, triflusulfuron-methyl, flazasulfuron, cyclosulfamuron, flupyrsulfuron, sulfosulfuron, azimsulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, for
  • imidazolinone herbicidal compounds such as imazamethabenz-methyl, imazamethapyr, imazamox, imazapyr, imazaquin, and imazethapyr;
  • sulfonamide herbicidal compounds such as flumetsulam, metosulam, diclosulam, florasulam, cloransulam-methyl, penoxsulam, and pyroxsulam;
  • pyrimidinyloxybenzoic acid herbicidal compounds such as pyrithiobac-sodium, bispyribac-sodium, pyriminobac- methyl, pyribenzoxim, and pyriftalid;
  • (22) other herbicidal compounds such as bentazon, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrole, cinmethylin, tridiphane, dalapon, diflufenzopyr- sodium, dithiopyr, thiazopyr, flucarbazone-sodium, propoxycarbazone-sodium, mefenacet, flufenacet, fentrazamide, cafenstrole, indanofan, oxaziclomefone, benfuresate, ACN, pyridate, chloridazon, norflurazon, flurtamone, diflufenican, picolinafen, beflubutamid, clomazone, amicarbazone, pinoxaden, and thiencarbazone- methyl .
  • active ingredients of the plant growth regulators include hymexazol, paclobutrazol, uniconazole-P, inabenfide, prohexadione-calcium, aviglycine, 1- naphthylacetamide, abscisic acid, indolebutyric acid, ethychlozate ethyl, ethephon, cloxyfonac, chlormequat, dichlorprop, gibberellin, prohydrojasmon, benzylaminopurine, forchlorfenuron, maleic hydrazide, calcium peroxide, mepiquat chloride) and 4 -CPA (4- chlorophenoxyacetic acid) .
  • Examples of active ingredients of the synergists include piperonyl butoxide, sesamex, sulfoxide, N- (2- ethylhexyl) -8,9, 10-trinorborn-5-ene-2 , 3-dicarboximide (MGK 264) , N-declyimidazole, WARF-antiresistant , TBPT, TPP, IBP, PSCP, methyl iodide (CH3I) , t-phenylbutenone, diethylmaleate, DMC, FDMC, ETP, and ETN.
  • active ingredients of the synergists include piperonyl butoxide, sesamex, sulfoxide, N- (2- ethylhexyl) -8,9, 10-trinorborn-5-ene-2 , 3-dicarboximide (MGK 264) , N-declyimidazole, WARF-antiresistant , TBPT, TPP, IBP, PSCP
  • active ingredients of the crop injury- reducing agents include benoxacor, cloquintocet-mexyl , cyometrinil, daimuron, dichlormid, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, mefenpyr- diethyl, MG191, oxabetrinil, allidochlor, isoxadifen-ethyl, cyprosulfamide, fluxofenim, and 1, 8-naphthalic anhydride.
  • Examples of pests on which the compound of the present invention exhibits a controlling effect include arthropod pests such as harmful insects and harmful mites, and more specifically, the following pets.
  • Planthoppers such as small brown planthopper ⁇ Laodelphax striatellus) , brown rice planthopper ⁇ Nilaparvata lugens) , and white-backed rice planthopper ⁇ Sogatella furcifera) ; leafhoppers (Deltocephalidae) such as green rice leafhopper ⁇ Nephotettix cincticeps) , green rice leafhopper ⁇ Nephotettix virescens) , and tea green leafhopper ⁇ Empoasca onukii) ; aphids (Aphididae) such as cotton aphid (Aphis gossypii) , green peach aphid ⁇ Myzus persicae) , cabbage aphid (Brevicoryne brassicae) , piraea aphid ⁇ Aphis spiraecola) , potato aphid ⁇ Macrosiphum e
  • Pyralid moths such as rice stem borer ⁇ Chilo suppressalis) , yellow rice borer ⁇ Tryporyza incertulas) , rice leafroller ⁇ Cnaphalocrocis medinalis) , cotton leafroller (Notarcha derogata) , Indian meal moth ⁇ Plodia interpunctella) , oriental corn borer ⁇ Ostrinia furnacalis) , cabbage webworm ⁇ Hellula undalis) , and bluegrass webworm (Pediasia teterrellus) ; owlet moths (Noctuidae) such as common cutworm ⁇ Spodoptera litura) , beet armyworm ⁇ Spodoptera exigua) , armyworm ⁇ Pseudaletia separata) , cabbage armyworm ⁇ Mamestra brassicae) , black cutworm ⁇ Agrotis ipsilon) , bee
  • Thysanoptera such as fall webworm ⁇ Hyphantria cunea
  • tineid moths such as casemaking clothes moth ⁇ Tinea translucens
  • webbing clothes moth ⁇ Tineola b ⁇ sselliella
  • Thrips such as yellow citrus thrips (Frankliniella occi.denta.lls), melon thrips (Thrips palml) , yellow tea thrips [Sclrtothrips dorsalis) , onion thrips ⁇ Thrips tahaci) , flower thrips (Frankliniella intonsa) , etc .
  • Culices such as common mosquito (Cul ⁇ x pipiens pallens) , Cluex tritaeniorhynchus, and Cluex quinquefasciatus; Aedes spp . such as yellow fever mosquito (Aedes aegypti) , and Asian tiger mosquito (Aedes albopictus) ; Anopheles spp.
  • Leafminer flies such as rice leafminer (Agromyza oryzae) , little rice leafminer (Hydrellia griseola) , tomato leafminer (Liriomyza sativae) , legume leafminer (Liriomyza trifolii) , and garden pea leafminer (Chromatomyia horticola)
  • Corn root worms ⁇ Diabrotica spp. such as Western corn root worm ⁇ Diabrotica virgifera virgifera) , and Sourthem corn root worm ⁇ Diabrotica undecimpunctata howardi) ; scarabs (Scarabaeidae) such as cupreous chafer ⁇ Anomala cuprea) , soybean beetle ⁇ Anomala rufocuprea) , and Japanese beetle ⁇ Popillia japonica) ; weevils such as maize weevil
  • leaf beetles Chrysomelidae
  • rice leaf beetle Olema oryzae
  • Asiatic locust ⁇ Locusta migratoria) , African mole cricket ⁇ Gryllotalpa africana) , rice grasshopper ⁇ Oxya yezoensis) , rice grasshopper (Oxya japonica) , Gryllidae, etc .
  • Cat flea (Ctenocephalides felis) , dog flea ⁇ Ctenocephalides canis) , human flea (Pulex irritans) , oriental rat flea ⁇ Xenopsylla cheopis) , etc.
  • Hymenoptera
  • Ants such as pharaoh ant ⁇ Monomorium pharaonis) , negro ant ⁇ Formica fusca japonica) , black house ant ⁇ Ochetellus glaber) , Pristomyrmex ponnes, Pheidole noda, leaf-cutting ant ⁇ Acromyrmex spp .
  • German cockroach [Blattella germanica) , smokybrown cockroach ⁇ Per ⁇ planeta fuliginosa) , American cockroach (Periplaneta americana) , Periplaneta brunnea, oriental cockroach ⁇ Blatta orientalis) ; Isoptera :
  • Termites such as Japanese subterranean termite (.Reticulitermes speratus) , Formosan subterranean termite ⁇ Coptotermes formosanus) , western drywood termite ⁇ Incisitermes minor), Daikoku drywood termite ( Cryptotermes domest ⁇ cus) , Odontotermes formosanus, Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Glyptotermes kodamai, Glyptotermes kushimensis, Japanese dampwood termite ⁇ Hodotermopsis japonica) , Coptotermes guangzhoensis, Reticulitermes miyatakei, eastern subterranean termite (Reticulitermes flavipes amamianus) , Reticulitermes sp.
  • Spider mites such as two-spotted spider mite ⁇ Tetranychus urticae) , Kanzawa spider mite ⁇ Tetranychus kanzawai) , citrus red mite (Panonychus citri) , European red mite ⁇ Panonychus ulmi) , and Oligonychus spp .
  • eriophyid mites such as pink citrus rust mite (Aculops pelekassi) , Phyllocoptruta citri, tomato rust mite ⁇ Aculops lycopersici) , purple tea mite ⁇ Calacarus carinatus) , pink tea rust mite ⁇ Acaphylla theavagran) , Eriophyes chibaensis, and apple rust mite (Aculus Louendali) ; tarosonemid mites (Tarsonemidae) such as broad mite ⁇ Polyphagotarsonemus latus) ; false spider mites (Tenuipalpidae) such as Brevipalpus phoenicis; Tuckerellidae; ticks (Ixodidae) such as Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanicus, American dog tick ticks (Ixodidae) such
  • Chilopoda house centipede ⁇ Thereuonema hilgendorfi) , Scolopendra subspinipes, etc.;
  • Diplopoda garden millipede ⁇ Oxidus gracilis) , Nedyopus tambanus, etc.;
  • Isopoda common pill bug (Armadillidium vulgare) , etc . ;
  • Gastropoda Limax marginatus, Limax flavus, etc.
  • the pesticidal composition comprising the compound of the present invention or a salt thereof can be used in the field of livestock disease therapy and livestock industry, and also can be used for exterminating organisms and parasites inhabiting the inside and/or outside of the body of vertebrates such as human being, cow, sheep, goat, pig, poulty, dog, cat and fish, to sustain public health.
  • organisms and parasites include ticks (Ixodes spp . ) (e.g. Ixodes scapularis) , Boophilus spp. (e.g. Boophilus microplus) , Amblyomma spp., Hyalomma spp., Rhipicephalus spp. (e.g.
  • Haemaphysalis spp. e.g. Haemaphysalis longicornis
  • dermacentor spp. e.g. dermacentor spp.
  • Ornithodoros spp. e.g.
  • Ornithodoros moubata parasitoid mites (Dermahyssus gallinae) , northern fowl mite (Ornithonyssus sylviarum) , itch mites (Sarcoptes spp.) (e.g Sarcoptes scabiei) , Psoroptes spp., Chorioptes spp., folicle mites (Demodex spp.), chiggers (Eutrombicula spp.), Aedes spp. (e.g.
  • Asian tiger mosquito (Aedes albopictus) ) , Anopheles spp., Culex spp., Culicodes spp., Musca spp., Hypoderma spp., Gasterophilus spp., Haematobia spp., Tabanus spp., Simulium spp., Triatoma spp., lice (Phthiraptera) (e.g. Damalinia spp . , Linognathus spp . , Haematopinus spp.), fleas (Ctenocephalides spp.) (e.g.
  • Nematoda for example, trichostrongyle (e.g. Nippostrongylus brasiliensis, Trichostrongylus axei, and Trichostrongylus colubriformis) , trichina (e.g. Trichinella spiralis), Haemonchus contortus, Nematodirus (e.g. Nematodirus battus) , Ostertagia circumcincta, Cooperia spp. , Hymenolepis nana, and the like.
  • trichostrongyle e.g. Nippostrongylus brasiliensis, Trichostrongylus axei, and Trichostrongylus colubriformis
  • Trichina e.g. Trichinella spiralis
  • Haemonchus contortus e.g. Nematodirus battus
  • Nematodirus e.g. Nematodirus battus
  • Ostertagia circumcincta Cooperia spp.
  • a pest controlling method comprising applying the compound of the present invention to a pest or a place where the pest inhabits also falls within the scope of the present invention.
  • the compound of the present invention or a salt thereof may be used as it is, and however, the compound of the present invention is usually formulated into the form of the pesticidal composition of the present invention as described above and then used.
  • the method of controlling a pest of the present invention comprises, for example, applying the compound of the present invention or a salt thereof or the pesticidal composition of the present invention to a pest or a place where the pest inhabits by a method same as to an application method for conventional pesticides, to allow the pest to contact with or ingest the compound of the present invention or a salt thereof or the pesticidal composition of the present invention.
  • Examples of the place where the pest inhabits include a paddy field, a dry field, a cultivated field, a tea field, a fruit orchard, a non-cultivated field, a house, a raising sesdling tray, a nursery box, nursery soil, a nursery mat, a water cluture medium in a hydroponic farm, and the like.
  • the spray treatment includes foliage spraying and truck spraying, and specifically comprises treating the plant surface or a pest itself with an active ingredient (the compound of the present invention or a salt thereof) , to exert a controlling effect on a pest.
  • the soil treatment comprises, for example, treating rhizosphere soil of a plant to be protected from damage such as eating by a pest with an active ingredient to control the pest directly, or allowing the active ingredient to permeate from the root and the like of the plant to inside of the plant to control the pest.
  • the soil treatment include planting hole treatment (planting hole spraying, soil incorporation after planting hole treatment) , plant foot treatment (plant foot spraying, soil incorporation at plant foot, plant foot drenching, plant foot treatment at a later seeding raising stage) , planting furrow treatment (planting furrow spraying, soil incorporation after planting furrow treatment) , planting row treatment (planting row spraying, soil incorporation after planting row treatment, planting row spraying at a growing stage) , planting row treatment at the time of sowing (planting row spraying at the time of sowing, soil incorporation after planting row treatment at the time of sowing) , broadcast treatment (overall soil surface spraying, soil incorporation after broadcast treatment) , other soil spraying treatment (foliar spraying of a granule at a growth stage, spraying under trunks or around main stems, soil surface spraying, soil surface incorporation, sowing hole spraying, furrow surface spraying, and spraying between plants) , other drenching treatment (soil drenching, d
  • the seed treatment comprises, for example, treating the seeds, seed potatoes or bulbs of a crop plant to be protected from damage such as eating by a pest, or the vicinity thereof with an active ingredient to exert a controlling effect on the pest.
  • the seed treatment include spraying, smearing, immersion, impregnation, application, film coating and pellet coating.
  • the water culture medium treatment comprises, for example, adding an active ingredient to a water culture medium or the like so as to allow the active ingredient to permeate from the root and the like of a crop plant to be protected from damage such as eating by a pest to inside of the plant, thereby the plant is protected from damage by the pest.
  • Specific examples of the water culture medium treatment include water culture medium incorporation, and water culture medium interfusion.
  • the application amount of the pesticidal composition of the present invention in the above-described application method may be appropriately changed depending on an application timing, an application place, a formulation form and the like, and it is usually 0.3 to 3,000 g, preferably 50 to 3,000 g of an active ingredient (the compound of the present invention or a salt thereof) per 1 hectare of soil where a plant is grown.
  • the pesticidal composition of the present invention is in the form of a wettable powder, it is preferred that it is diluted with water to 0.1 to 1,000 ppm, preferably from 10 to 500 ppm of the active ingredient and then applied.
  • the pesticidal composition of the present invention or a water dilution thereof may be applied directly to a pest or a plant such as a crop plant to be protected from the pest.
  • the soil of a cultivated field may be treated with the pesticidal composition of the present invention or a water dilution thereof so as to control pests inhabiting the soil.
  • the pesticidal composition of the present invention when in the form of resin formulation, it can be processed into the form of a sheet or a string, and then applied by winding it around a crop plant, disposing it in the vicinity of a crop plant, laying it on the soil surface at the plant feet, or the like.
  • the application amount is usually 0.001 to 10 mg/m 3 of the compound of the present invention as the active ingredient for application to space, and 0.001 to 100 mg/m 2 of the compound of the present invention as the active ingredient for application to a plane.
  • the pesticidal composition in the form of an emulsifiable concentrate, a wettable powder or a flowable formulation is usually applied after dilution with water so as to contain usually 0.001 to 10,000 ppm of the active ingredient.
  • the pesticidal composition in the form of an oil solution, an aerosol formulation, a smoking pesticide or a poison bait is usually applied as it is.
  • the pesticidal composition of the present invention When the pesticidal composition of the present invention is used for controlling external parasites of livestock such as a cow, a horse, a pig, a sheep, a goat and a chicken, or small animals such as a dog, a cat, a rat and a mouse, it can be applied to said animals by a known method in the veterinary field. Specifically, when systemic control is intended, the pesticidal composition of the present invention is administered, for example, as a tablet, a mixture with feed, a suppository or an injection (e.g., intramuscularly, subcutaneously, intravenously, intraperitoneally, etc.).
  • livestock such as a cow, a horse, a pig, a sheep, a goat and a chicken
  • small animals such as a dog, a cat, a rat and a mouse
  • the pesticidal composition of the present invention is administered, for example, as a tablet, a mixture with feed, a
  • a method of using the pesticidal composition of the present invention includes spraying, pour-on treatment or a spot-on treatment with the pesticidal composition in the form of an oil solution or an aqueous liquid, washing an animal with the pesticidal composition in the form of a shampoo formulation, and attachment of a collar or a ear tag made of the pesticidal composition in the form of a resin formulation to an animal.
  • the amount of the compound of the present invention is usually in the range of 0.1 to 1,000 mg per 1 kg body weight of the animal .
  • reagent for TLC Kiesel Gel 60F 254 (70 to 230 mesh) manufactured by Merck or a detection method by UV light were used.
  • reagent for column chromatography for example, silica gel 60 (spherical, particle size: 63 to 210 nm) manufactured by Kanto Chemical Co., Inc., or Florisil (100 to 200 mesh) manufactured by Wako Pure Chemical Industry Inc. was used.
  • medium pressure preparative HPCL for example, Ultrapack (filler: silica gel) manufactured by Yamazen K. K. were used.
  • tetramethylsilane was used as an internal standard, and for example, JEOL AL-400 Bruker AVANCE 400 was used (measurement temperature was 25°C unless otherwise stated) .
  • measurement temperature was 25°C unless otherwise stated.
  • trace amount melting point measurement meter manufactured by Yanagimoto Seisakusho K. K. were used.
  • Production Examples 208 to 261 The following compounds were produced according to the methods of Production Example 207.
  • N- [1- (4-chlorophenyl) -3- (4-fluorophenylthio) -2- propenylidene] -3-chloroaniline (Hereinafter described as the present compounds 300 to 302)
  • a methanol solution (15 ml) of N- [1- (4- chlorophenyl) -3-trimethylsilyl-2-propylidene] -3-chloroaniline (1.2 g)
  • a methanol solution (5 ml) of 4- fluorothiophenol (0.44 g) was dropped under ice cool and the mixture was stirred for 22 hours at room temperature.
  • N- [1- (4-chlorophenyl) -3- (4-fluorophenylthio) -2-methyl- 2-propenylidene] -4-methylaniline (Hereinafter, this compound is referred to as "present compound 310".)
  • THF tetrahydrofuran
  • 1- (4-chlorophenyl) -2-methyl-2-propen-l-one (2.1 g) and triethylamine (3 drops) a THF solution (5 ml) containing 4-fluorothiophenol (1.49 g) was dropped under ice cool and the mixture was stirred at room temperature for 6 hours.

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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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Composé imine α, β-insaturée ayant la formule ci-dessous, dans laquelle A désigne un groupe phényle ou analogue, où le cycle hétéro aromatique forme une liaison carbone-carbone ayant la chaîne principale du composé, R désigne un atome d'hydrogène ou un groupe alkyle en C1 à C5 éventuellement substitué par un atome d'halogène, chaque p, q et r désigne un nombre entier de 0 à 5; X1s, X2s ou X3s peuvent être différents entre eux, dans le cas où p, q ou r est égal ou supérieur à 2; X1, X2 et X3 désignent, respectivement, un groupe hydrocarbure à chaîne en C1 à C6, éventuellement substitué par au moins l'un des groupes A, ou analogues.
PCT/JP2008/068522 2007-10-11 2008-10-07 Composé imine insaturée et son utilisation pour la protection phytosanitaire Ceased WO2009048152A2 (fr)

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JP2007265299 2007-10-11

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012072489A1 (fr) 2010-11-29 2012-06-07 Bayer Cropscience Ag Imine alpha-bêta insaturée
US11426412B2 (en) 2017-10-18 2022-08-30 Jubilant Epipad LLC Imidazo-pyridine compounds as PAD inhibitors
US11459338B2 (en) 2017-11-24 2022-10-04 Jubilant Episcribe Llc Heterocyclic compounds as PRMT5 inhibitors
US11529341B2 (en) 2018-03-13 2022-12-20 Jubilant Prodel LLC Bicyclic compounds as inhibitors of PD1/PD-L1 interaction/activation
US11629135B2 (en) 2017-11-06 2023-04-18 Jubilant Prodell Llc Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation
US11833156B2 (en) 2017-09-22 2023-12-05 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors

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US10640457B2 (en) 2009-12-10 2020-05-05 The Trustees Of Columbia University In The City Of New York Histone acetyltransferase activators and uses thereof
EP2509590B1 (fr) * 2009-12-10 2019-10-30 The Trustees of Columbia University in the City of New York Activateurs d'histone acétyltransférase et utilisation de ceux-ci
JP2016029022A (ja) * 2012-12-21 2016-03-03 日本曹達株式会社 １−アリール−１−ヘテロジエン化合物および有害生物防除剤

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ES2175168T3 (es) * 1995-11-28 2002-11-16 Kimberly Clark Co Compuestos de colorantes estabilizados por la luz.
BRPI0619187A2 (pt) * 2005-12-01 2011-09-13 Sumitomo Chemical Co composto de iminopropeno e uso do mesmo

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012072489A1 (fr) 2010-11-29 2012-06-07 Bayer Cropscience Ag Imine alpha-bêta insaturée
US9055743B2 (en) 2010-11-29 2015-06-16 Bayer Intellectual Property Gmbh Alpha, beta-unsaturated imines
US11833156B2 (en) 2017-09-22 2023-12-05 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors
US12357639B2 (en) 2017-09-22 2025-07-15 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors
US11426412B2 (en) 2017-10-18 2022-08-30 Jubilant Epipad LLC Imidazo-pyridine compounds as PAD inhibitors
US11629135B2 (en) 2017-11-06 2023-04-18 Jubilant Prodell Llc Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation
US11459338B2 (en) 2017-11-24 2022-10-04 Jubilant Episcribe Llc Heterocyclic compounds as PRMT5 inhibitors
US11529341B2 (en) 2018-03-13 2022-12-20 Jubilant Prodel LLC Bicyclic compounds as inhibitors of PD1/PD-L1 interaction/activation

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WO2009048152A3 (fr) 2009-09-11
JP2009108051A (ja) 2009-05-21
TW200922468A (en) 2009-06-01
AR070656A1 (es) 2010-04-28

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