WO2008075465A1 - Composition insecticide pour une graine végétale ou une culture et utilisation de celle-ci - Google Patents

Composition insecticide pour une graine végétale ou une culture et utilisation de celle-ci Download PDF

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Publication number
WO2008075465A1
WO2008075465A1 PCT/JP2007/001424 JP2007001424W WO2008075465A1 WO 2008075465 A1 WO2008075465 A1 WO 2008075465A1 JP 2007001424 W JP2007001424 W JP 2007001424W WO 2008075465 A1 WO2008075465 A1 WO 2008075465A1
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group
alkyl
haloalkyl
substituted
haloalkoxy
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PCT/JP2007/001424
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English (en)
Japanese (ja)
Inventor
Michikazu Nomura
Naofumi Tomura
Atsuko Kawahara
Hidenori Daido
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Mitsui Chemicals, Inc.
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Publication of WO2008075465A1 publication Critical patent/WO2008075465A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms

Definitions

  • Insecticidal composition for plant seeds or crops and method of use
  • the present invention relates to a novel insecticidal composition and a novel preventive method for preventing insect damage by applying the insecticidal composition to plant seeds or crops of agricultural plants.
  • WO 2005/021488 Pamphlet ⁇ and WO 2005/0731 65 Pamphlet ⁇ have descriptions of insecticides and methods of use.
  • Patent Document 1 International Publication No. 2005/021488 Pamphlet
  • Patent Document 2 International Publication No. 2005/0731 No. 65 Pamphlet
  • an object of the present invention is to provide an insecticidal composition capable of preventing various insect damages in plant seeds or crops of agricultural plants and a new method for preventing various insect damages.
  • the present invention is as follows.
  • ⁇ 2 , ⁇ 3 , ⁇ 4 each represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom
  • R 1 R 2 independently represents a hydrogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 alkyl group,
  • G ⁇ , G 2 represents an oxygen atom or a sulfur atom independently of one another
  • X may be the same or different and each represents a hydrogen atom, a halogen atom, a C 1 -C 3 alkyl group, or a trifluoromethyl group,
  • ⁇ represents an integer from 0 to 4,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1—C 3 haloalkylsulfonyl group C1-C4 alkylamino group, di-C1-
  • Carbocyclic group (wherein the carbocyclic group is a naphthyl group, a tetrahydronaphthyl group, an indanyl group, a fluorenyl group, a 9_oxofluorenyl group, an adamantanyl group, an anthracenyl group, or a norphenyl group. ),
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4 alkenyl group, C2-C4-haloalkenyl group, C2 — C 4 alkynyl group, C 2— C 4 haloalkynyl group, C 3— C 8 cycloalkyl group, C 3— C 8 halocycloalkyl group, C 1—C 3 alkoxy group, C 1—C 3 haloalkoxy group Group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3-alkylsulfinyl group, C1-C3-haloalkylsulfinyl group, C1-C3-alkylsulfonyl group, C1-C 3haloalkylsulfonyl group, C1-C4 alkylamino group, di-
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4 alkenyl group, C2-C4-haloalkenyl group, C2 — C 4 alkynyl group, C 2— C 4 haloalkynyl group, C 3— C 8 cycloalkyl group, C 3— C 8 halocycloalkyl group, C 1—C 3 alkoxy group, C 1—C 3 haloalkoxy group Group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3-alkylsulfinyl group, C1-C3-haloalkylsulfinyl group, C1-C3-alkylsulfonyl group, C1-C 3haloalkylsulfonyl group, C1-C4 alkylamino group, di-
  • Birazinyl group Pyridyl group, Pyridine mono-N-oxide group, Pyrimidinyl group, Pyridazyl group, Furyl group, Cenyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Imidazolyl group, Imidazolyl group Group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1 H-isoindolyl group 2,3-dihydromonobenzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, acrylidinyl
  • a naphthyl group, a tetrahydronaphthyl group, a C 3 -C 8 cycloalkyl group, an indanyl group, a fluorenyl group, a 9_oxofluorenyl group, an adamantanyl group, or a norphenyl group is shown.
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4 alkenyl group, C2-C4-haloalkenyl group, C2 — C 4 alkynyl group, C 2— C 4 haloalkynyl group, C 3— C 8 cycloalkyl group, C 3— C 8 halocycloalkyl group, C 1—C 3 alkoxy group, C 1—C 3 haloalkoxy group Group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3-alkylsulfinyl group, C1-C3-haloalkylsulfinyl group, C1-C3-alkylsulfonyl group, C1-C 3haloalkylsulfonyl group, C1-C4 alkylamino group, di-
  • Birazinyl group Pyridyl group, Pyridine mono-N-oxide group, Pyrimidinyl group, Pyridazyl group, Furyl group, Cenyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Imidazolyl group, Imidazolyl group Group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1 H-isoindolyl group 2,3-dihydromonobenzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, benzoimidazoly
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2 — C 4 alkynyl group, C 2—C 4 haloalkynyl group, C3—C 8 cycloalkyl group, C 3—C 8 halocycloalkyl group, C 1—C3 alkoxy group, C 1—C 3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3-alkylsulfinyl group, C1-C3-haloalkylsulfinyl group, C1-C3-alkylsulfonyl group, C1-C3-haloalkyl group Sulfonyl group, C1-C4 alkylamino group, C
  • Halogen atom C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3 — C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group Group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, Nitro group, hydroxy group, C
  • ⁇ 2 , ⁇ 3 , ⁇ 4 , ⁇ 5 may be the same or different, a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl group,
  • Halogen atom C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkyl Sulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1- C 4 alkylcarbonyl group, C 1—C4 haloalkyl carbonyl group, C 1—C 4 alkyl carbonyloxy group, C 1—C4 haloalkylcarbonyl group, C 1—C 4 alkoxycarbonyl group, C 1—C 4 Haloalkoxycarbonyl group, C1-C
  • C1-C6 haloalkyl group C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3- C 8 cycloalkyl group, C 3 _C 8 halocycloalkyl group, C 1—C 6 alkoxy group, C 1—C 6 haloalkoxy group,
  • substituents which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • a C1-C6 haloalkyl group optionally substituted by one or more hydroxyl groups
  • a C 1 -C 6 alkyl group optionally substituted with one or more C 1 -C 6 haloalkyl groups,
  • substituents which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1—C 3 haloalkylsulfonyl group C1-C4 alkylamino group, di-C1-
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4 alkenyl group, C2-C4-haloalkenyl group, C2 — C 4 alkynyl group, C 2— C 4 haloalkynyl group, C 3— C 8 cycloalkyl group, C 3— C 8 halocycloalkyl group, C 1—C 3 alkoxy group, C 1—C 3 haloalkoxy group Group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3-alkylsulfinyl group, C1-C3-haloalkylsulfinyl group, C1-C3-alkylsulfonyl group, C1-C 3haloalkylsulfonyl group, C1-C4 alkylamino group, di-
  • Birazinyl group Pyridyl group, Pyridine mono-N-oxide group, Pyrimidinyl group, Pyridazyl group, Furyl group, Cenyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Imidazolyl group, Imidazolyl group Group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1 H-isoindolyl group 2,3-dihydromonobenzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or dihydrovillaryl
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4 alkenyl group, C2-C4-haloalkenyl group, C2 — C 4 alkynyl group, C 2— C 4 haloalkynyl group, C 3— C 8 cycloalkyl group, C 3— C 8 halocycloalkyl group, C 1—C 3 alkoxy group, C 1—C 3 haloalkoxy group Group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3-alkylsulfinyl group, C1-C3-haloalkylsulfinyl group, C1-C3-alkylsulfonyl group, C1-C 3haloalkylsulfonyl group, C1-C4 alkylamino group, di-
  • ⁇ 5 may be the same or different, Halogen atom, C1-C4 alkyl group, C1-C4 haloalkyl group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group Group, C 1 -C 3 alkylsulfonyl group, C 1 -C 3 haloalkylsulfonyl group, or cyan group,
  • ⁇ 3 is ⁇ 2—C 6 perfluoroalkyl group, C 1—C 6 perfluoroalkyl thio group, C 1—C 6 perfluoroalkylsulfinyl group, or C 1—C 6 perfluoroalkylsulfonyl Except when it is a group. ),
  • Upsilon 8 may be the same or different
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4 alkenyl group, C2-C4-haloalkenyl group, C2 — C 4 alkynyl group, C 2— C 4 haloalkynyl group, C 3— C 8 cycloalkyl group, C 3— C 8 halocycloalkyl group, C 1—C 3 alkoxy group, C 1—C 3 haloalkoxy group Group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3-alkylsulfinyl group, C1-C3-haloalkylsulfinyl group, C1-C3-alkylsulfonyl group, C1-C 3haloalkylsulfonyl group, C1-C4 alkylamino group, di-
  • Birazinyl group Pyridyl group, Pyridine mono-N-oxide group, Pyrimidinyl group, Pyridazyl group, Furyl group, Cenyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Imidazolyl group, Imidazolyl group Group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1 H-isoindolyl group 2,3-dihydromonobenzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or dihydrovillaryl
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1—C 3 haloalkylsulfonyl group C1-C4 alkylamino group, di-C1-
  • ⁇ 6 and ⁇ 9 may be the same or different, and a halogen atom, C 1—C 4 alkyl group, C 1 _C 4 haloalkyl group, C 1—C 3 alkylthio group, C 1—C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C
  • Y 8 represents C 1 —C4 haloalkoxy group, C 2—C 6 perfluoroalkyl group, C 1—C6 perfluoro group.
  • a 1 represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom
  • a 2 , A 3 and A 4 represent carbon atoms
  • R 1 R 2 independently represents a hydrogen atom or a C 1 -C 4 alkyl group
  • G and G 2 each independently represent an oxygen atom or a sulfur atom
  • X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
  • ⁇ represents an integer from 0 to 4,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1-
  • a substituted phenyl group having one or more substituents which may be the same or different selected from
  • Birazinyl group Pyridyl group, Pyridine mono-N-oxide group, Pyrimidinyl group, Pyridazyl group, Furyl group, Chenyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Imidazolyl group, Imidazolyl group Group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydromonobenzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydrobiranyl group, or dihydrovillaryl group
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1-
  • ⁇ 5 may be the same or different
  • Halogen atom C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio Group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, cyano group, or Indicates nitro group
  • ⁇ 2 and ⁇ 4 may be the same or different
  • Trifluoromethyl group C1-C6 perfluoroalkoxy group, pentafluorosulfanyl group,
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • C1-C6 haloalkylsulfinyl groups or
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • a 1 represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom
  • a 2 , A 3 and A 4 represent carbon atoms
  • R 1 R 2 independently represents a hydrogen atom or a C 1 -C 4 alkyl group
  • G and G 2 each independently represent an oxygen atom or a sulfur atom
  • X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
  • ⁇ represents an integer from 0 to 4,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1—C 3 haloalkylsulfonyl group C1-C4 alkylamino group, di-C1-
  • a substituted phenyl group having one or more substituents which may be the same or different selected from Heterocyclic group (What is the heterocyclic group here?
  • Birazinyl group Pyridyl group, Pyridine mono-N-oxide group, Pyrimidinyl group, Pyridazyl group, Furyl group, Chenyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Imidazolyl group, Imidazolyl group Group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydromonobenzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydrobiranyl group, or dihydrovillaryl group
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4 alkenyl group, C2-C4-haloalkenyl group, C2 — C 4 alkynyl group, C 2— C 4 haloalkynyl group, C 3— C 8 cycloalkyl group, C 3— C 8 halocycloalkyl group, C 1—C 3 alkoxy group, C 1—C 3 haloalkoxy group Group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3-alkylsulfinyl group, C1-C3-haloalkylsulfinyl group, C1-C3-alkylsulfonyl group, C1-C 3haloalkylsulfonyl group, C1-C4 alkylamino group, di-
  • Halogen atom C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkyl Sulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1- C 4 alkylcarbonyl group, C 1—C4 haloalkyl carbonyl group, C 1—C 4 alkyl carbonyloxy group, C 1—C4 haloalkylcarbonyl group, C 1—C 4 alkoxycarbonyl group, C 1—C 4 A haloalkoxycarbonyl group, a
  • Halogen atom C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group C 1 -C 6 alkylsulfinyl group, C 1 -C 6 haloalkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, cyano group, or nitro group
  • ⁇ 2 and ⁇ 4 may be the same or different
  • C 1—C 4 haloalkoxy group C 2—C 6 perfluoroalkyl group, C 1—C 6 perfluoroalkylthio group, C 1 _C 6 perfluoroalkylsulfinyl group, C 1— C 6 perfluoroalkylsulfonyl group,
  • Trifluoromethyl group C1-C6 perfluoroalkoxy group, pentafluorosulfanyl group,
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substitutions which may be the same or different selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C 1 -C 6 alkoxy group, or a C 1 -C 6 haloalkoxy group
  • substitutions which may be the same or different selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C 1 -C 6 alkoxy group, or a C 1 -C 6 haloalkoxy group
  • substitutions which may be the same or different selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C 1 -C 6 alkoxy group, or a C 1 -C 6 haloalkoxy group
  • a 1 represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom
  • a 2 , A 3 and A 4 represent carbon atoms
  • R 1 R 2 independently represents a hydrogen atom or a C 1 -C 4 alkyl group
  • G and G 2 each independently represent an oxygen atom or a sulfur atom
  • X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
  • ⁇ represents an integer from 0 to 4,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1— C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1
  • a substituted phenyl group having one or more substituents which may be the same or different selected from
  • Birazinyl group Pyridyl group, Pyridine mono-N-oxide group, Pyrimidinyl group, Pyridazyl group, Furyl group, Chenyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Imidazolyl group, Imidazolyl group Group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydromonobenzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydrobiranyl group, or dihydrovillaryl group
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1— C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1
  • Y is C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkyl group Represents a sulfinyl group, a C1-C6 alkylsulfonyl group, or a C1-C6 haloalkylsulfonyl group, Y 5 is
  • Halogen atom C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group C 1 -C 6 alkylsulfinyl group, C 1 -C 6 haloalkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, cyano group, or nitro group
  • ⁇ 2 and ⁇ 4 may be the same or different
  • Y 3 represents a halogen atom.
  • a 1 represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom
  • a 2 , A 3 and A 4 represent carbon atoms
  • R 1 R 2 independently represents a hydrogen atom or a C 1 -C 4 alkyl group
  • G and G 2 each independently represent an oxygen atom or a sulfur atom
  • X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
  • ⁇ represents an integer from 0 to 4,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1-
  • a substituted phenyl group having one or more substituents which may be the same or different selected from
  • Birazinyl group Pyridyl group, Pyridine mono-N-oxide group, Pyrimidinyl group, Pyridazyl group, Furyl group, Chenyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Imidazolyl group, Imidazolyl group Group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydromonobenzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydrobiranyl group, or dihydrovillaryl group
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1-
  • Y 5 may be the same or different
  • Halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group C 1 -C 6 alkylsulfinyl group, C 1 _C 6 haloalkylsulfinyl group, C 1—C 6 alkylsulfonyl group, C 1—C 6 haloalkylsulfonyl group, cyano group, nitro group, ⁇ 2 , ⁇ 4 may be the same or different, hydrogen atom A halogen atom, a C 1 -C 6 alkyl group,
  • Ra represents a halogen atom or a hydroxy group
  • Rb and Rc can each independently represent a hydrogen atom, a hydroxy group, a halogen atom or a C1-C6 haloalkyl group, and at least one of Rb and Rc has one or more hydrogen atoms, a hydroxy group, Has a chlorine, bromine, or iodine atom.
  • a 2 , A 3 and A 4 each represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom
  • Z represents _N (F ⁇ ) SC ⁇ G ⁇ or _N (RjG ⁇
  • R 1 R 2 independently of one another represents a hydrogen atom, a C 1 -C 4 alkyl group, or a C 1 -C 4 alkyl group.
  • G 2 represents an oxygen atom or a sulfur atom
  • X may be the same or different and each represents a hydrogen atom, a halogen atom, a C 1 -C 3 alkyl group, or a trifluoromethyl group, n represents an integer from 0 to 4,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1—C 3 haloalkylsulfonyl group C1-C4 alkylamino group, di-C1-
  • a naphthyl group, a tetrahydronaphthyl group, a C 3 -C 8 cycloalkyl group, an indanyl group, a fluorenyl group, a 9_oxofluorenyl group, an adamantanyl group, or a norphenyl group is shown.
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 _ C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, C1-C4 alkylamino Group, di-C1
  • a substituted carbocyclic group having one or more substituents which may be the same or different from each other (wherein the carbocyclic group is a naphthyl group, a tetrahydronaphthyl group, a C3-C8 cycloalkyl group, an indanyl group) , Fluorenyl group, 9_oxofluorenyl group, adamantanyl group, or norpoxyl group).
  • Birazinyl group Pyridyl group, Pyridine mono-N-oxide group, Pyrimidinyl group, Pyridazyl group, Furyl group, Cenyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Imidazolyl group, Imidazolyl group Group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1 H-isoindolyl group 2,3-dihydromonobenzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or dihydrovillaryl
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4 alkenyl group, C2-C4-haloal group Kenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 halo Alkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1- C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1-C
  • Birazinyl group Pyridyl group, Pyridine mono-N-oxide group, Pyrimidinyl group, Pyridazyl group, Furyl group, Cenyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Imidazolyl group, Imidazolyl group Group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1 H-isoindolyl group 2,3-dihydromonobenzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or dihydrovillaryl
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C 1 _C 4 alkyl group, C2—C4 alkenyl group, C 2—C 4 haloalkenyl group, C 2—C 4 alkynyl group, C 2—C 4 haloalkynyl group, C3—C 8 cycloalkyl group, C 3—C 8 halocycloalkyl group, C 1—C3 alkoxy group, C 1—C 3 haloalkoxy group, C 1—C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group Group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, C1-C4 alkylamino group,
  • a naphthyl group, a tetrahydronaphthyl group, a C 3 -C 8 cycloalkyl group, an indanyl group, a fluorenyl group, a 9_oxofluorenyl group, an adamantanyl group, or a norphenyl group is shown.
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1—C 3 haloalkylsulfonyl group C1-C4 alkylamino group, Di-C1-
  • Birazinyl group Pyridyl group, Pyridine mono-N-oxide group, Pyrimidinyl group, Pyridazyl group, Furyl group, Cenyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Imidazolyl group, Imidazolyl group Group, triazolyl group, pyrazolyl group, tetrazolyl group, benzothiazolyl group, benzoxazolyl group, benzofuranyl group, benzothiophenyl group, quinolyl group, isoquinolyl group, indolyl group, isoindolyl group, 1 H-isoindolyl group 2,3-dihydromonobenzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydropyranyl group, or dihydrovillaryl
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4 alkenyl group, C2-C4-haloalkenyl group, C2 — C 4 alkynyl group, C 2— C 4 haloalkynyl group, C 3— C 8 cycloalkyl group, C 3— C 8 halocycloalkyl group, C 1—C 3 alkoxy group, C 1—C 3 haloalkoxy group Group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C 3haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1
  • a method for preventing insect damage which comprises applying the insecticidal composition according to any one of [1] to [7] to plant seeds.
  • a method for preventing insect damage comprising contacting the plant seed with the insecticidal composition according to any one of [1] to [7].
  • Plant seeds are corn, soybeans, red beans, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, syaendu, kapochya, sugar cane, tobacco, peppers and rapeseed rape, taro, potato
  • a method for preserving plant seeds comprising applying the insecticidal composition according to any one of [1] to [7] to plant seeds.
  • a method for preserving a crop comprising applying the insecticidal composition according to any one of [1] to [7] to a crop of an agricultural plant.
  • an insecticidal composition capable of showing a high preventive effect against insect damage occurring on plant seeds or crops of agricultural plants, and a method for preventing various insect damages.
  • C a _C b (a, b represents an integer of 1 or more)”, for example, “C 1 _C 3” has 1 to 3 carbon atoms.
  • ⁇ C 2 _C 6 '' means 2 to 6 carbon atoms, and ⁇ C 1 _C4 '' means 1 to 4 carbon atoms.
  • N- means normal, "i-” means iso, “s_” means secondary, and "t-" means single.
  • Halogen atom includes fluorine atom, chlorine atom, bromine atom or iodine atom.
  • C 1 _C 3 alkyl group examples include linear or branched alkyl groups having 1 to 3 carbon atoms such as methyl, ethyl, n-propyl, i-propyl, cyclopropyl and the like.
  • the “C 1 -C 4 alkyl group” includes, for example, a linear or branched chain such as n-butyl, s-butyl, i-butyl, t-butyl, etc.
  • Examples thereof include alkyl groups having 1 to 4 carbon atoms, and examples of the “C 1 -C 6 alkyl group” include “C 1 -C 4 alkyl group”, for example, n-pentyl, 2 —pentyl, 3 —pentyl. , Neopentyl, n-hexyl, 2-hexyl, 4_methyl_2_pentyl, 3_methyl-n-pentyl, etc., linear or branched alkyl groups having 1 to 6 carbon atoms It is done.
  • Examples of the substituent of “substituted C 1 -C 4 alkyl group” include a halogen atom, a C 1 -C 4 haloalkyl group, a C 2 -C 4 alkenyl group, a C 2 -C 4 haloalkenyl group, a C 2 -C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group Group, C 1 -C 3 haloalkylthio group, C 1 -C 3 alkylsulfinyl group, C 1 -C 3 haloalkylsulfinyl group, C 1 -C 3 alkylsulfonyl group, C 1-C 3 haloalkylsul
  • C 1 -C 3 haloalkyl group examples include monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, 1_fluoroethyl, 2_Fluoroethyl, 2, 2-Difluoroethyl, 2, 2, 2_Trifluoroethyl, 1_Chloroethyl, 2_Chloroethyl, 2,2-Dichloroethyl, 2, 2, 2_Trichloroethyl, 1-Bromo Til, 2-bromoethyl, 2,2_dibromoethyl, 2,2,2-trib mouth, moethyl, 2_ethyl, pentafluoroethyl, 3_fluoro-n_propyl, 3-chloro mouth, n-propyl, 3 —Bromo
  • C 1 _C 3 haloalkyl group for example, it is substituted by one or more halogen atoms which may be the same or different, such as 4_fluoro-n-butyl, nonafluoro-n_butyl, nonafluoro-2-butyl, etc.
  • C 1 _C 6 haloalkyl group examples include, for example, 6, 6, 6-trifluoro-n-hexyl in addition to “C 1 -C 4 haloalkyl group”, Nonafluoro-n-butyl, nonafluoro_2_butyl, etc., which may be the same or different, linear or branched alkyl group having 1 to 6 carbon atoms substituted by one or more halogen atoms Is mentioned.
  • Examples of the "C2_C4 alkenyl group” include alkenyl having 2 to 4 carbon atoms having a double bond in a carbon chain such as vinyl, allyl, 2-butenyl, and 3-butenyl.
  • Examples of the “C 2 -C 4 haloalkenyl group” include 3, 3-difluoro-2-propenyl, 3,3-dichloro 1-propenyl, 3,3-dibromo 1 2_propenyl, 2,3_dibromo 1_propenyl, 4,4-difluoro-3-butenyl, 3,4,4_tribromo_3-butenyl etc. may be the same or different one or more Examples thereof include a linear or branched alkenyl group having 2 to 4 carbon atoms having a double bond in a carbon chain substituted by a halogen atom.
  • Examples of the “C 2 -C 4 alkynyl group” include a triple bond in a carbon chain such as propargyl, 1-butyne _ 3 _yl, 1-butyne 3 _methyl _ 3 -yl.
  • Straight chain or branched chain alkynyl groups having 2 to 4 carbon atoms, and examples of the “C 2 -C 4 haloalkynyl group” include one or more halo groups which may be the same or different. Examples thereof include a linear or branched alkynyl group having 2 to 4 carbon atoms having a triple bond in a carbon chain substituted by a mouth atom.
  • Examples of the "C3-C8 cycloalkyl group” include carbon atoms having a cyclic structure such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl, cycloheptyl and the like. Examples thereof include cycloalkyl groups having 3 to 8 atoms.
  • C 3 -C 8 halocycloalkyl group examples include 2, 2, 3, 3-tetrafluorocycloptyl, 2-chlorocyclohexyl, 4 —C3-C8 cycloalkyl group having a cyclic structure substituted by one or more halogen atoms which may be the same or different, such as chlorocyclohexyl.
  • Examples of the "C1-C3 alkoxy group” include linear or branched alkoxy groups having 1 to 3 carbon atoms such as methoxy, ethoxy, n_propyloxy, and isopropyloxy.
  • a group such as “C 1-C 4 alkoxy group”.
  • C 1 _C 3 alkoxy group for example, a linear or branched alkoxy group having 1 to 4 carbon atoms such as 2_butoxy is exemplified, and “C 1-C 3 haloalkoxy”
  • ⁇ group '' examples include trifluoromethoxy, 1,1,2_trifluoroethoxy, 1,1,1,3,3,3_hexafluorone 2-propyloxy, 2,2,2_trifluoroethoxy , 2_black ethoxy, 3_fluoro-n-propyloxy, 1,1,2,2,2-tetrafluoroethoxy, 1,1,2,3,3,3_hexafluoropropyloxy
  • a linear or branched haloalkoxy group having 1 to 3 carbon atoms substituted with one or more halogen atoms and the “C 1 _C 4 haloalkoxy group”
  • ⁇ C 1 _C 3 haloalkoxy group '' for example, for example
  • Examples of the "C1-C3 alkylthio group” include linear or branched alkylthio having 1 to 3 carbon atoms such as methylthio, ethylthio, n-propylthio, i-propylthio, cyclopropylthio and the like.
  • Examples of the “C 1 -C 4 alkylthio group” include “C 1 -C 3 alkylthio group”, for example, n_ptylthio, i_ptylthio, s_ptylthio, t_ptylthio, cyclopropylmethylthio, etc.
  • C 1 -C 6 alkylthio group includes, for example, n— Examples thereof include linear or branched alkylthio groups having 1 to 6 carbon atoms such as pentylthio and n-hexylthio.
  • C1-C3 haloalkylthio group examples include trifluoromethylthio, pentafluoroethylthio, 2_fluoroethylthio, 2, 2, 2-trifluoroethylthio, Heptafluoro_n-propylthio, heptaflu Oro i —propylthio, 1, 1, 2, 2, 2-tetrafluoroethylthio, 1, 1, 2, 3, 3, 3_hexafluoropropylthio, etc.
  • C 1 _C4 haloalkylthio group includes “C 1 -C 3 haloalkylthio group”.
  • nonafluoro-n_ptylthio, nonafluoro-s_ptylthio, 4,4,4_trifluoro-n_ptylthio, etc. which may be the same or different, straight chain substituted by one or more halogen atoms
  • C1-C6 haloalkylthio groups include C1-C4 haloalkylthio groups, for example, in addition to C1-C4 haloalkylthio groups.
  • Owl n-pentylthio A linear or branched alkylthio group having 1 to 6 carbon atoms substituted with one or more halogen atoms, which may be the same or different, such as perfluoro-n-hexylthio; .
  • Examples of the "C1-C3 alkylsulfinyl group” include linear or branched carbon atoms such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, cyclopropylsulfinyl and the like.
  • Examples of the “C 1 _C 6 alkyl sulfinyl group” include “C 1 -C 3 alkyl sulfinyl group” in addition to “C 1 -C 3 alkyl sulfinyl group”. Examples thereof include linear or branched alkylsulfinyl groups having 1 to 6 carbon atoms such as n-pentylsulfinyl and n-hexylsulfinyl.
  • Examples of the "C 1 -C 3 haloalkylsulfinyl group” include trifluoromethylsulfinyl, pentafluorosulfinyl, 2, 2, 2-trifluoroethylsulfinyl, heptafluoro n-propylsulfinyl, heptafluoro _ i —Propylsulfinyl, 1,1,2,2,2-tetrafluoroethylsulfinyl, 1,1,2,3,3,3_hexafluoropropylsulfinyl, etc.
  • C 1 -C 3 haloalkylsulfinyl group examples include nonafluoro-n-butylsulfinyl, nonafluoro-s-butylsulfinyl, 4, 4, 4 _Trifluoro-n-butylsulfinyl, perfluoro mouth _ n-pentylsulfinyl, perfluoro-n-hexylsulfinyl, etc., linear, substituted with one or more halogen atoms, which may be the same or different Alternatively, branched alkylsulfinyl groups having 1 to 6 carbon atoms can be mentioned.
  • Examples of the "C1-C3 alkylsulfonyl group” include linear or branched carbon atoms such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, cyclopropylpropyl and the like.
  • C 1 -C 6 alkylsulfonyl group examples include “C 1 -C 3 alkylsulfonyl group”, for example, n_methylsulfonyl, t-butylsulfonyl, Examples thereof include linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms such as n-pentylsulfonyl and n-hexylsulfonyl.
  • Examples of the "C1-C3 haloalkylsulfonyl group” include trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2, 2, 2_trifluoroethylsulfonyl, heptafluoro_n_propylsulfonyl, heptafluoro_ one or more, which may be the same or different, such as i-propylsulfonyl, 1,1,2,2,2-tetrafluoroethylsulfonyl, 1,1,2,3,3,3_hexafluoropropylsulfonyl
  • Examples of the “C 1 -C 6 haloalkylsulfonyl group” include a linear or branched alkylsulfonyl group having 1 to 3 carbon atoms substituted by a halogen atom, and “C 1 -C 6 haloalkylsulfonyl
  • one Furuoro n- pentylsulfonyl be the same or different, such as path one Furuoro to n- Kishirusuruhoniru And a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms substituted by one or more halogen atoms.
  • arylsulfonyloxy group examples include phenylsulfonyloxy, p-toluenesulfonyloxy, 1_naphthylsulfonyloxy, 2-naphthylsulfonyloxy, anthrylsulfonyloxy, Examples include arylsulfonyl groups having 6 to 14 carbon atoms having an aromatic ring such as phenanthrylsulfonyloxy and acenaphthylenylsulfonyloxy.
  • Examples of the “C 1 -C 4 alkylamino group” include linear, branched or cyclic such as methylamino, ethylamino, n-propylamino, i-propylamino, n_ptylamino, cyclopropylamino and the like. Examples thereof include alkylamino groups having 1 to 4 carbon atoms. Examples of the “di-C 1 -C 4 alkylamino group” include the same or the same such as dimethylamino, jetylamino, 1 ⁇ 1 _ethyl_ 1 ⁇ 1 _methylamino, etc. Examples thereof include an amino group substituted by two linear or branched alkyl groups having 1 to 4 carbon atoms which may be different.
  • C 1 -C 4 perfluoroalkyl group examples include trifluoromethyl, pentafluoroethyl, heptafluoro_n-propyl, heptafluoro i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, Nonafluoro-i—a linear or branched alkyl group having 1 to 4 carbon atoms, all substituted by fluorine atoms such as ptyl, and the like
  • “C 2 _C 6 perfluoroalkyl group” includes, for example, Pentafluoroethyl, heptafluoro-n _propyl, heptafluoro mouth i-propyl, nonafluo mouth n_ ptyl, nonafluoro-2-ptyl, nonafluoro-i _ ptyl, unde force fluoro n-penty
  • Examples of the “C 1 -C 6 perfluoroalkylthio group” include trifluoromethylthio, pentafluoroethylthio, heptafluoro_n-propylthio, heptafluorine i-propylthio, nonafluoron-butylthio 1 to 6 linear or branched carbon atoms, all substituted by fluorine atoms such as nonafluoro-2-ptylthio, nonafluoro-i_ptylthio, unde-forced fluoro-n-pentylthio, tridecafluoro-n-hexylthio, etc.
  • alkylthio group include trifluoromethylthio, pentafluoroethylthio, heptafluoro_n-propylthio, heptafluorine i-propylthio, nonafluoron-butylthio 1 to 6 linear or
  • Examples of the "C 1 -C 6 perfluoroalkylsulfinyl group” include trifluoromethylsulfinyl, pentafluoroethylsulfinyl, heptafroro_n-propylsulfinyl, heptafluor mouthpiece i-propyls Linear, all substituted by fluorine atoms such as rufinyl, nonafluoro-n-butylsulfinyl, nonafluoro-2_ptylsulfinyl, nonafluoro-i_ptylsulfinyl, undecafluoro-n-pentylsulfinyl, tridecafluoro-n-hexylsulfinyl, etc.
  • branched alkyl sulfinyl groups having 1 to 6 carbon atoms can be mentioned.
  • C 1 -C 6 perfluoroalkylsulfonyl group examples include trifluoromethylsulfonyl, pentafluoroethylsulfonyl, heptafluoro n_propylsulfonyl, heptafluoro mouthpiece i-propylsulfonyl Linear or all substituted by fluorine atoms such as nonafluoro-n_ptylsulfonyl, nonafluoro-2-ptylsulfonyl, nonafluoro-i-butylsulfonyl, undefluoro-n-pentylsulfonyl, tridecafluoro-n-hexylsulfonyl Examples include branched-chain alkylsulfonyl groups having 1 to 6 carbon atoms.
  • alkylsilyl group examples include linear or branched alkyl groups having a key atom such as a methylsilyl group, a trimethylsilyl group, and an ethylsilyl group.
  • general formula (1) or general formula (5) It may contain one or more asymmetric carbon atoms or asymmetric centers, and there may be more than one optical isomer, but it is represented by general formula (1) or general formula (5).
  • the compound includes all the optical isomers and mixtures containing them in an arbitrary ratio.
  • general formula (1) or general formula (5 ) May have two or more geometric isomers derived from a carbon-carbon double bond in the structural formula, but in general formula (1) or general formula (5)
  • the compounds represented include all geometric isomers and mixtures containing them in any proportion.
  • A is a carbon atom, a nitrogen atom or an oxidized nitrogen atom
  • a 2 , A 3 and A 4 are all carbon atoms
  • Preferred is a hydrogen atom or a C1_C4 alkyl group, and more preferred is a hydrogen atom, a methyl group or an ethyl group.
  • R 2 is preferably a hydrogen atom or a C 1 -C4 alkyl group, and more preferably a hydrogen atom, a methyl group, or an ethyl group.
  • G 1 G 2 are preferably both oxygen atoms.
  • n is preferably 0, 1, or 2 and more preferably 0 or 1.
  • X is preferably a hydrogen atom or a halogen atom, more preferably
  • a hydrogen atom or a fluorine atom A hydrogen atom or a fluorine atom.
  • a phenyl group, or a halogen atom a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, C1-C3 haloalkyl
  • Q 2 is preferably a substituted phenyl group or a substituted pyridyl group represented by the general formula (2), the general formula (3) or the general formula (4).
  • ⁇ 5 are preferably the same or different, and fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, ⁇ _propyl group, i-propyl group, n_butyl group, 2_butyl Group, trifluoromethyl group, methylthio group, methylsulfinyl group, methylsulfonyl group, trifluoromethylthio group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, cyan group,
  • ⁇ 2 and ⁇ 4 are preferably hydrogen atoms
  • Upsilon 3 triflumizole Ruo Russia methyl, penta full O B Sulfur D group,
  • 1,1,2,2,3,3,3_hexafluoropropoxy group 2,2,2_trifluoro- 1_trifluoromethylethoxy group, 2_trifluoromethoxy--1,1,2,2_trifluoro Fluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group,
  • 1,1,2,2,3,3,3_hexafluoropropylsulfonyl group 2,2,2_trifluoromethyl 1_trifluoromethylmethylsulfonylsulfonyl group, 2_trimethyl Fluoromethoxy-1, 1,1,2_trifluoroethylsulfonyl group, 1,1,2,2-tetrafluoroethylsulfonyl group,
  • the Upsilon 5 a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, methylation group, Echiru group, .eta. propyl group, i - propyl group, n _ butyl group, 2 _ butyl group, triflate Ruo b methyl
  • ⁇ 2 and ⁇ 4 are preferably hydrogen atoms
  • Y is preferably a trifluoromethoxy group, a pentafluoroethyl group, a trifluoromethylthio group, a pentafluoroethylthio group, a heptafluoropropylthio group, a heptafluoroisopropylthio group, a trifluoromethylsulfinyl group, a pentafluoro group.
  • Oloethylsulfinyl group heptafluoropropylsulfinyl group, heptafluoroisopropylsulfinyl group, trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, heptafluoropropylsulfonyl group, heptafluoroisopropylsulfonyl group
  • ⁇ 5 is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, a trifluoromethoxy group, a pentafluoroethyl group, a Rifluoromethylthio group, pentafluoroethylthio group, heptafluoropropylthio group, heptafluoroisopropylthio group, trifluoromethylsulfinyl group, pentafluoroethylsulfinyl group, heptafluoropropylsulfinyl group, Heptafluoroisopropylsulfinyl group, trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, heptafluoropropylsulfonyl group, heptafluoroisopropy
  • ⁇ 2 and ⁇ 4 are preferably hydrogen atoms
  • ⁇ 3 is a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and in the case of general formula (4)
  • ⁇ 5 are preferably the same or different, and fluorine atom, chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, ⁇ _propyl group, i-propyl group, n_butyl group, 2_butyl Group, trifluoromethyl group, methylthio group, methylsulfinyl group, methylsulfonyl group, trifluoromethylthio group, trifluoromethylsulfinyl group, trifluoromethylsulfonyl group, cyan group,
  • ⁇ 2 and ⁇ 4 are preferably hydrogen atoms
  • R a is a promodifluoro group
  • Rb is a fluorine atom
  • R c force ⁇ trifluoromethyl group
  • R a is a chlorodifluoro group
  • Rb is a hydroxy group
  • Rc is a chlorofluoromethyl group.
  • Examples of the compound represented by the general formula (1) include the following compounds I to VI I I. These compounds can be preferably used from the viewpoint of controlling effect.
  • a 1 represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom
  • a 2 , A 3 and A 4 represent carbon atoms
  • R 1 R 2 independently represents a hydrogen atom or a C 1 -C 4 alkyl group G and G 2 each independently represent an oxygen atom or a sulfur atom,
  • X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
  • n an integer from 0 to 4,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4 alkenyl group, C2-C4-haloalkenyl group, C2 — C 4 alkynyl group, C 2— C 4 haloalkynyl group, C 3— C 8 cycloalkyl group, C 3— C 8 halocycloalkyl group, C 1—C 3 alkoxy group, C 1—C 3 haloalkoxy group Group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3-alkylsulfinyl group, C1-C3-haloalkylsulfinyl group, C1-C3-alkylsulfonyl group, C1-C 3haloalkylsulfonyl group, C1-C4 alkylamino group, di-
  • a substituted phenyl group having one or more substituents which may be the same or different selected from
  • Birazinyl group Pyridyl group, Pyridine mono-N-oxide group, Pyrimidinyl group, Pyridazyl group, Furyl group, Chenyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl Group, pyruyl group, imidazolyl group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydromonobenzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydrobiranyl group, Or dihydrovinyl group
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1—C 3 haloalkylsulfonyl group C1-C4 alkylamino group, di-C1-
  • ⁇ 5 may be the same or different
  • Halogen atom C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group C 1 -C 6 alkylsulfinyl group, C 1 -C 6 haloalkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, cyano group, or nitro group
  • ⁇ 2 and ⁇ 4 may be the same or different
  • Trifluoromethyl group C1-C6 perfluoroalkoxy group, pentafluorosulfanyl group,
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group Substituted C 1—C6 halo An alkylthio group,
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • C1-C6 haloalkylsulfinyl groups or
  • substituents which may be the same or different, selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group Represents a substituted C 1 -C 6 haloalkylsulfonyl group.
  • a 1 represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom
  • a 2 , A 3 and A 4 represent carbon atoms
  • R 1 R 2 independently represents a hydrogen atom or a C 1 -C 4 alkyl group
  • G and G 2 each independently represent an oxygen atom or a sulfur atom
  • X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
  • ⁇ represents an integer from 0 to 4,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1— C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1
  • a substituted phenyl group having one or more substituents which may be the same or different selected from
  • Birazinyl group Pyridyl group, Pyridine mono-N-oxide group, Pyrimidinyl group, Pyridazyl group, Furyl group, Chenyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Imidazolyl group, Imidazolyl group Group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydromonobenzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydrobiranyl group, or dihydrovillaryl group
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1— C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1
  • Halogen atom C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkyl Sulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano group, nitro group, hydroxy group, C1- C 4 alkylcarbonyl group, C 1—C4 haloalkyl carbonyl group, C 1—C 4 alkyl carbonyloxy group, C 1—C4 haloalkylcarbonyl group, C 1—C 4 alkoxycarbonyl group, C 1—C 4 Haloalkoxycarbonyl group, C1-C
  • Halogen atom C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group C 1 -C 6 alkylsulfinyl group, C 1 -C 6 haloalkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, cyano group, or nitro group
  • ⁇ 2 and ⁇ 4 may be the same or different
  • C 1—C 4 haloalkoxy group C 2—C 6 perfluoroalkyl group, C 1—C 6 perfluoroalkylthio group, C 1 _C 6 perfluoroalkylsulfur group Cinyl group, C 1 _C 6 perfluoroalkylsulfonyl group,
  • Trifluoromethyl group C1-C6 perfluoroalkoxy group, pentafluorosulfanyl group,
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substituents which may be the same or different and selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group
  • substitutions which may be the same or different selected from a hydrogen atom, a hydroxy group, a chlorine atom, a bromine atom, an iodine atom, a C 1 -C 6 alkoxy group, or a C 1 -C 6 haloalkoxy group And represents a substituted C 1 -C 6 haloalkylsulfonyl group substituted by a group.
  • Compound II represented by:
  • a 1 represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom
  • a 2 , A 3 and A 4 represent carbon atoms
  • R 1 R 2 independently represents a hydrogen atom or a C 1 -C 4 alkyl group
  • G and G 2 each independently represent an oxygen atom or a sulfur atom
  • X may be the same or different and is a hydrogen atom, a halogen atom, or a trifluoromethyl group, n represents an integer from 0 to 4,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1—C 3 haloalkylsulfonyl group C1-C4 alkylamino group, di-C1-
  • a substituted phenyl group having one or more substituents which may be the same or different selected from
  • Birazinyl group Pyridyl group, Pyridine mono-N-oxide group, Pyrimidinyl group, Pyridazyl group, Furyl group, Chenyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Imidazolyl group, Imidazolyl group Group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydromonobenzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydrobiranyl group, or dihydrovillaryl group Indicates. ),
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1—C 3 haloalkylsulfonyl group C1-C4 alkylamino group, di-C1-
  • Y is C 1 _C 6 alkoxy group, C 1—C 6 haloalkoxy group, C 1—C 6 alkylthio group, C 1—C 6 haloalkylthio group, C 1—C6 alkylsulfinyl group, C 1—C 6 haloalkylsulfinyl.
  • Halogen atom C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group C 1 -C 6 alkylsulfinyl group, C 1 -C 6 haloalkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylsulfonyl group, cyano group, or nitro group
  • ⁇ 2 and ⁇ 4 may be the same or different
  • Y 3 represents a halogen atom.
  • a 1 represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom
  • a 2 , A 3 and A 4 represent carbon atoms
  • R 1 R 2 independently represents a hydrogen atom or a C 1 -C 4 alkyl group
  • G and G 2 each independently represent an oxygen atom or a sulfur atom
  • X may be the same or different and is a hydrogen atom, a halogen atom, or A rifluoromethyl group,
  • n an integer from 0 to 4,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1—C 3 haloalkylsulfonyl group C1-C4 alkylamino group, di-C1-
  • a substituted phenyl group having one or more substituents which may be the same or different selected from
  • Birazinyl group Pyridyl group, Pyridine mono-N-oxide group, Pyrimidinyl group, Pyridazyl group, Furyl group, Chenyl group, Oxazolyl group, Isoxazolyl group, Oxadiazolyl group, Thiazolyl group, Isothiazolyl group, Thiadiazolyl group, Imidazolyl group, Imidazolyl group Group, triazolyl group, pyrazolyl group, tetrazolyl group, 2,3-dihydromonobenzo [1,4] dioxinyl group, benzo [1,3] dioxolyl group, tetrahydrobiranyl group, or dihydrovillan Le group
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, substituted C1-C4 alkyl group, C2-C4-alkenyl group, C2-C4-haloalkenyl group, C2-C 4 alkynyl group, C2-C4 haloalkynyl group, C3-C8 cycloalkyl group, C3-C8 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1 —C 3 alkylthio group, C 1 —C 3 haloalkylthio group, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1—C 3 haloalkylsulfonyl group C1-C4 alkylamino group, di-C1-
  • Ra represents a halogen atom or a hydroxy group
  • Rb and Rc are each independently a hydrogen atom, a hydroxy group, a halogen atom or
  • a C 1 -C 6 haloalkyl group can be shown, and at least one of Rb and Rc has one or more hydrogen atom, hydroxy group, chlorine atom, bromine atom, or iodine atom.
  • At least one of R 2 is C 1 _C
  • the compound represented by the general formula (1) or the general formula (5) can be produced by the production methods 1-11 described below.
  • a typical production method of the compound represented by the general formula (1) or the general formula (5) is shown below, but the production method is not limited to the production method shown below.
  • Y 5 is ⁇ 2 , ⁇ 3 , ⁇ 4 in the above [1],
  • the solvent is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • water aromatic hydrocarbons such as benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, etc.
  • Halogenated hydrocarbons linear ether or cyclic ethers such as jetyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxetane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, acetone, methyl isopti Must be an inert solvent such as ketones such as ruketone and cyclohexanone, amides such as dimethylformamide and dimethylacetamide, nitriles such as acetonitrile, 1,3-dimethyl-2-imidazolidinone, etc. These solvents can be used alone or in combination Combined and can be used.
  • organic bases such as triethylamine, tri-n-ptylamine, pyridine, 4-dimethylaminopyridine, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium hydrogen carbonate , Carbonates such as lithium carbonate, phosphates such as dipotassium monohydrogen phosphate and trisodium phosphate, alkali metal hydrides such as sodium hydride, alkali metals such as sodium methoxide and sodium ethoxide It can indicate alcoholate.
  • these bases may be appropriately selected and used within a range of 0.01 to 5 molar equivalents relative to the compound represented by the general formula (19).
  • the reaction temperature may be appropriately selected from -20 ° C to the reflux temperature of the solvent used, and the reaction time may be selected from a range of several minutes to 96 hours.
  • m_nitroaromatic carboxylic acid halide when the compound represented by the general formula (19) is m_nitroaromatic carboxylic acid halide, m_nitro aromatic force ruponic acid halide is halogenated with the corresponding aromatic carboxylic acid.
  • the halogenating agent include halogenating agents such as thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, and phosphorus trichloride.
  • the compound represented by the general formula (2 1) is obtained.
  • the production method described in C chem. Ber. P. 788 (1 970) that is, using an additive such as 1-hydroxybenzotriazol as appropriate
  • a method using a condensing agent using a catalyst can be shown.
  • Other condensing agents used in this case may include 1_ethyl_3_ (3-dimethylaminopropyl) carbodiimide, 1, 1'-carbonyl bis-1H-imidazole, etc. .
  • Both the method using a condensing agent and the mixed acid anhydride method are not limited to the solvent, reaction temperature, and reaction time described in the above-mentioned literature, and use an inert solvent that does not significantly inhibit the progress of the reaction as appropriate.
  • the reaction temperature and reaction time may be appropriately selected according to the progress of the reaction.
  • the compound represented by the general formula (2 1) can be led to the compound represented by the general formula (22) by a reduction reaction.
  • the reduction reaction include a method using a hydrogenation reaction and a method using a metal compound (for example, stannous chloride (anhydride), iron powder, zinc powder, etc.).
  • the reaction can be carried out in a suitable solvent, in the presence of a catalyst, at normal pressure or under pressure, in a hydrogen atmosphere.
  • the catalyst include a palladium catalyst such as palladium, a nickel catalyst such as Raney nickel, a cobalt catalyst, a ruthenium catalyst, a rhodium catalyst, and a platinum catalyst.
  • Solvents include water, methanol, ethanol, and the like.
  • Alcohols such as benzene and toluene, chain or cyclic ethers such as ether, dioxane and tetrahydrofuran, and esters such as ethyl acetate.
  • the pressure is 0.1 to 1 OMPa
  • the reaction temperature is _20 ° C to the reflux temperature of the solvent used
  • the reaction time is appropriately selected from a few minutes to 96 hours. A compound can be produced efficiently.
  • the compound represented by the general formula (24) By reacting the compound represented by the general formula (22) and the compound represented by the general formula (23) in a solvent, the compound represented by the general formula (24) can be produced. In this step, a base can also be used.
  • the solvent is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • water aromatic hydrocarbons such as benzene, toluene and xylene, dichloromethane, chloroform, carbon tetrachloride, etc.
  • Halogenated hydrocarbons, chain ethers and cyclic ethers such as jetyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxetane, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, acetone, methyl isopti Must be an inert solvent such as ketones such as ruketone and cyclohexanone, amides such as dimethylformamide, dimethylacetamide, nitriles such as acetonitrile, 1,3-dimethyl-2-imidazolidinone These solvents can be used alone or in combination Combined and can be used.
  • organic bases such as triethylamine, tri-n-ptylamine, pyridine, 4-dimethylaminopyridine, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium hydrogen carbonate Carbonates such as potassium carbonate, phosphates such as dipotassium monohydrogen phosphate and trisodium phosphate, alkali metal hydrides such as sodium hydride, alkali metals such as sodium methoxide and sodium ethoxide It can indicate alcoholate.
  • These bases may be appropriately selected and used within the range of 0.01 to 5 molar equivalents relative to the compound represented by the general formula (2 2).
  • the reaction temperature may be appropriately selected from _20 ° C. to the reflux temperature of the solvent used, and the reaction time may be in the range of several minutes to 96 hours. Further, it can also be produced by the method using the condensing agent described in 1_ (i) or the mixed acid anhydride method.
  • the compound represented by the general formula (2 6) and the compound represented by the general formula (2 5) are reacted in a solvent or without a solvent to produce the compound represented by the general formula (2 6).
  • Examples of the compound represented by the general formula (25) include alkyl halides such as methyl iodide, iodyl chloride, and n-propyl bromide, and halogenated acyls such as acetyl chloride. it can.
  • a suitable base or solvent can be used, and as the base or solvent, those exemplified in the above 1_ (i) can be used.
  • the reaction temperature, reaction time, and the like can also follow the example of 1_ (i).
  • Q 1 and Q 2 are synonymous, L represents a functional group having a leaving ability such as /, a valence atom, and a hydroxy group, and H a I represents a halogen atom.
  • the compound represented by the general formula (28) is used as the condensing agent as described in 1 above (i).
  • the compound represented by the general formula (30) can be produced by reacting with the compound represented by the general formula (20) according to the conditions using the mixed acid anhydride method.
  • R 2 , X, n, and Q 1 Q 2 have the same meanings as AA 2 , A 3 , A 4 , R 1 R 2 , X, n, and Q 1 Q 2 in [1]. )
  • the compounds represented by the general formula (3 5) and the general formula (3 6) can be produced according to the conditions described in 3_ (i) above. it can. Conditions such as solvent and reaction temperature are not limited to those described in the literature. These two compounds can be easily separated and purified by a known separation and purification technique such as silica gel column chromatography.
  • L represents a functional group having a leaving ability such as a halogen atom or a hydroxy group.
  • an amination reaction is performed using ammonia, and the general formula (3 8
  • the conditions for the reaction solvent and the like are not limited to those described in the literature, and an inert solvent that does not significantly inhibit the progress of the reaction can be used as appropriate.
  • the reaction temperature and reaction time may be appropriately selected according to the progress of the reaction.
  • an aminating agent in addition to ammonia, methylamine, ethylamine and the like can also be shown.
  • a compound represented by the general formula (39) is obtained by reacting the compound represented by the general formula (38) with the compound represented by the general formula (23) according to the conditions described in 1_ (i) above. Can be manufactured.
  • R 2 , Y 2 , Y 4 are
  • [1] is synonymous with R 2 , ⁇ 2 , and Y 4 , and Y 5 independently represents a hydrogen atom, a methyl group, a chlorine atom, a bromine atom, or an iodine atom.
  • 3 ⁇ 4 or 1 _ ⁇ 6 represents a perfluoroalkyl group, and m represents 1 or 2.
  • Examples of the compound represented by the general formula (4 1) include trifluoromethyl iodide, pentafluoroethyl iodide, heptafluoro_n-propyl iodide, iodine Heptafluoroisopropyl iodide, nonafluoroiodide n_ptyl, nonafluoro-2-iotyl iodide, and the like, which are represented by 1 to 10 with respect to the compound represented by the general formula (40) What is necessary is just to use suitably in the range of a double molar equivalent.
  • the solvent used in this step is not limited to the solvents described in the above-mentioned documents, and any solvent may be used as long as it does not significantly inhibit the progress of this reaction.
  • a fragrance such as water, benzene, toluene, xylene, etc.
  • Aromatic hydrocarbons, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, chain or cyclic ethers such as jetyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxetane, ethyl acetate, butyl acetate, etc.
  • Esters alcohols such as methanol and ethanol, ketones such as acetone, methylisobutylketone and cyclohexanone, amides such as dimethylformamide and dimethylacetamide, and nitriles such as acetonitrile. , 1,3-Dimethyl_2_imidazolidinone, hexame
  • An inert solvent such as trimethyl triphosphate can be used, and these solvents can be used alone or in combination of two or more.
  • a polar solvent is particularly preferable.
  • the reaction temperature may be appropriately selected from _20 ° C to the reflux temperature of the solvent used, and the reaction time may be in the range of several minutes to 96 hours.
  • halogenating agent examples include chlorine, bromine, iodine, N_chlorosuccinic acid imide, N-prosuccinic acid imide, N-chlorosuccinic acid imide, and the like. 1 to 1 for the compound represented by formula (42) What is necessary is just to use suitably in the range of 0 times molar equivalent.
  • the solvent to be used is not limited to the solvents described in the above-mentioned documents, and the solvent does not significantly inhibit the progress of this reaction.
  • water aromatic hydrocarbons such as benzene, toluene, xylene, halogenated hydrocarbons such as dichloromethane, black mouth form, and carbon tetrachloride, jetyl ether, dioxane, tetrahydrofuran, 1 , 2-Dimethoxetane and other chain or cyclic ethers, Ethyl acetate, Esters such as butyl acetate, Alcohols such as methanol and ethanol, Ketones such as Acetone, Methylisobutylketone, Cyclohexanone, Dimethyl Amides such as formamide and dimethylacetamide, nitriles such as acetonitrile 1, 3-dimethyl-one 2 _ imidazolidinone
  • the compound represented by the general formula (44) can be produced.
  • the method described in T etrahedron Lett. P. 49 55 (1 994) is shown. it can.
  • oxidizing agent examples include organic peracids such as m_peroxybenzoic acid, sodium metaperoxide, hydrogen peroxide, ozone, selenium dioxide, chromic acid, dinitrogen tetroxide, and acyl chloride. Iodine, bromine, N-promosuccinic acid imide, benzoylpentyl, hypochlorous acid t-butyl, etc. can be shown.
  • the solvent used in this step is not limited to the solvent described in the above-mentioned document, and any solvent may be used as long as it does not significantly inhibit the progress of this reaction. These solvents may be used alone or in combination of two kinds. They can be used in combination. A polar solvent is particularly preferable.
  • the reaction temperature may be appropriately selected from -20 ° C to the reflux temperature of the solvent to be used, and the reaction time may be selected from a range of several minutes to 96 hours.
  • 6- (iv): General formula (43) ⁇ General formula (43_2) By using an appropriate methylating agent, the compound represented by general formula (43) is converted to general formula (43-2) (formula among, Upsilon either the 5 can be produced a compound represented by the always. showing a methyl group). As this method, for example, the method described in T etrahedron Lett, p. 6237 (2000) can be shown.
  • Y 2 , ⁇ 4 , and ⁇ 5 in the general formula (2) are 0 1 _ 6 6 -fluoroalkylthio groups, C 1 _C 6 trifluoroalkylsulfinyl groups, A compound represented by general formula (1) or general formula (5) which is a C 1 _C 6 perfluoroalkylsulfonyl group can be produced.
  • the compound represented by the general formula (47) can be produced.
  • the compound represented by the general formula (1) or the general formula (5) can be produced.
  • Y 2 , ⁇ 4 , and ⁇ 5 in the general formula (2) are 0 1 _ 6 6 fluoralkylthio groups, C 1 _C 6 trifluoroalkylsulfinyl groups, A compound represented by general formula (1) or general formula (5) which is a C 1 _C 6 perfluoroalkylsulfonyl group can be produced.
  • AA 2 , A 3 , A 4 , X, n, G 2 , R 2 , Q 2 are AA 2 , A 3 in the above [1]. , A 4 , X, n, G 2 , R 2 , and Q 2 .
  • the compound represented by the general formula (48) can be produced by reacting the compound represented by the general formula (48) with a reactant in a solvent using a base.
  • the solvent may be any solvent that does not significantly inhibit the progress of this reaction.
  • aliphatic hydrocarbons such as hexane, cyclohexane, and methylcyclohexane, benzene, xylene, toluene, and the like.
  • Aromatic hydrocarbons Dichloromethane, Chloroform, Carbon tetrachloride, Halogenated hydrocarbons such as 1,2-Dichloroethane, Jetyl ether, Dioxane, Tetrahydrofuran, Ethers such as 1,2-Dimethetane, Dimethyl Amides such as formamide and dimethylacetamide, nitriles such as acetonitrile and propionitryl, acetone, methylisobutyl ketone, cyclohexanone, methyl It can indicate solvents such as ketones such as ethyl ketone, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethyl sulfoxide and water. These solvents can be used alone or in combination of two or more.
  • Examples of the base include organic bases such as trytylamine, triptylamin, pyridine, and 4-dimethylaminopyridine, sodium hydroxide hydroxides such as sodium hydroxide and hydroxy hydroxide, sodium hydrogen carbonate, Carbonates such as carbonated lithium, phosphates such as potassium monohydrogen phosphate and trisodium phosphate, metal hydride metal salts such as sodium hydride, sodium methoxide, sodium methoxide, etc. Examples thereof include alkenyl trimetallic alkoxides, organolithiums such as n-butyllithium, and Grignard reagents such as ethylmagnesium bromide.
  • organic bases such as trytylamine, triptylamin, pyridine, and 4-dimethylaminopyridine
  • sodium hydroxide hydroxides such as sodium hydroxide and hydroxy hydroxide
  • sodium hydrogen carbonate Carbonates such as carbonated lithium
  • phosphates such as potassium monohydrogen phosphate
  • bases may be appropriately selected from the range of 0.01 to 5 times the molar equivalent of the compound represented by the general formula (4 8), or may be used as a solvent.
  • Examples of the reactant include halogenated alkyls such as methyl iodide, acetyl bromide, trifluoromethyl iodide, 2,2,2_trifluoroethyl iodide, and allylic iodide.
  • Halogenated, propargyl bromide such as propargyl bromide
  • halogenated acyls such as acetyl chloride
  • acid anhydrides such as trifluoroacetic anhydride
  • alkyl sulfates such as dimethyl sulfate and jetyl sulfate.
  • reactants may be appropriately selected within the range of 1 to 5 molar equivalents relative to the compound represented by the general formula (4 8), or may be used as a solvent.
  • the reaction temperature is from 80 ° C to the reflux temperature of the solvent used, and the reaction time is from several minutes to 9
  • AA 2 , A 3 , A 4 , X, n, G 2 , R 1 R 2 , Q 2 are A 1, A in the above [1] 2 , A 3 , A 4 , X, n, G 2 , R 1 R 2 , Q 2 is synonymous.
  • the compound represented by the general formula (22) is reacted with an aldehyde or ketone in a solvent, a catalyst is added, and the reaction is performed in a hydrogen atmosphere to produce the compound represented by the general formula (50). be able to.
  • the solvent may be any solvent that does not significantly inhibit the progress of this reaction.
  • aliphatic hydrocarbons such as hexane, cyclohexane, and methylcyclohexane, benzene, xylene, toluene, and the like.
  • Aromatic hydrocarbons Dichloromethane, Chloroform, Carbon tetrachloride, Halogenated hydrocarbons such as 1,2-Dichloroethane, Jetyl ether, Dioxane, Tetrahydrofuran, Ethers such as 1,2-Dimethetane, Dimethyl Amides such as formamide and dimethylacetamide, nitriles such as acetonitrile and propionitryl, ketones such as acetone, methylisobutylketone, cyclohexanone and methylethylketone, esters such as ethyl acetate and butyl acetate 1, 3-Dimethyl 1 _Imidazolidino , Sulfolane, dimethylsulfoxide, alcohols such as methanol and ethanol, and solvents such as water. These solvents can be used alone or in combination of two or more.
  • Examples of the catalyst include palladium catalysts such as palladium-carbon, palladium hydroxide-carbon, nickel catalysts such as Raney-nickel, cobalt catalysts, platinum catalysts, ruthenium catalysts, rhodium catalysts, etc. so Monkey.
  • palladium catalysts such as palladium-carbon, palladium hydroxide-carbon
  • nickel catalysts such as Raney-nickel
  • cobalt catalysts platinum catalysts, ruthenium catalysts, rhodium catalysts, etc. so Monkey.
  • aldehydes examples include aldehydes such as formaldehyde, acetoaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoracetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, and promoacetoaldehyde. Can be shown.
  • ketones examples include ketones such as acetone, perfluoroacetone, and methyl ethyl ketone.
  • reaction pressure may be appropriately selected within the range of 1 atm to 100 atm.
  • the reaction temperature may be appropriately selected from 120 ° C. to the reflux temperature of the solvent to be used, and the reaction time may be appropriately selected within the range of several minutes to 96 hours.
  • the solvent may be any solvent that does not significantly inhibit the progress of this reaction.
  • aliphatic hydrocarbons such as hexane, cyclohexane, and methylcyclohexane, benzene, xylene, toluene, and the like.
  • Aromatic hydrocarbons Dichloromethane, Chloroform, Carbon tetrachloride, Halogenated hydrocarbons such as 1,2-Dichloroethane, Jetyl ether, Dioxane, Tetrahydrofuran, Ethers such as 1,2-Dimethetane, Dimethyl Amides such as formamide and dimethylacetamide, nitriles such as acetonitrile and propionitryl, ketones such as acetone, methylisobutylketone, cyclohexanone and methylethylketone, esters such as ethyl acetate and butyl acetate 1, 3-Dimethyl 1 _Imidazolidino , Sulfolane, dimethylsulfoxide, alcohols such as methanol and ethanol, and solvents such as water. These solvents can be used alone or in combination of two or more.
  • the reducing agent include podium hydrides such as sodium polohydride, sodium cyano
  • aldehydes include aldehydes such as formaldehyde, acetoaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoracetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, and promoacetoaldehyde. Can be shown.
  • ketones include ketones such as acetone, perfluoroacetone, and methyl ethyl ketone.
  • the reaction temperature may be appropriately selected from 120 ° C to the reflux temperature of the solvent to be used, and the reaction time may be appropriately selected from the range of several minutes to 96 hours.
  • the solvent may be any solvent that does not significantly inhibit the progress of this reaction.
  • aliphatic hydrocarbons such as hexane, cyclohexane, methylcyclohexane, benzene, xylene, toluene, etc.
  • Aromatic hydrocarbons Dichloromethane, Chloroform, Carbon tetrachloride, Halogenated hydrocarbons such as 1,2-Dichloroethane, Jetyl ether, Dioxane, Tetrahydrofuran, Ethers such as 1,2-Dimethetane, Dimethyl Amides such as formamide and dimethylacetamide, nitriles such as acetonitrile and propionitryl, ketones such as acetone, methylisobutylketone, cyclohexanone and methylethylketone, esters such as ethyl acetate and butyl acetate 1, 3-Dimethyl 1 _Imidazolid Emissions, sulfolane, dimethyl sulfoxide, alcohols such as methanol, ethanol, a solvent such as water can with this showing, and these solvents may be used alone or two or more Monkey.
  • Halogenated hydrocarbons such as 1,2-Dichloroethane, Jety
  • Examples of the formylating agent include formic acid anhydrides such as formaldehyde, formic acid, fluoroformatic acid, formyl (2,2-dimethylpropionic acid), formic acid esters such as phenyl formate, pentafluoro oral benzaldehyde, Can indicate oxazole and the like.
  • formic acid anhydrides such as formaldehyde, formic acid, fluoroformatic acid, formyl (2,2-dimethylpropionic acid)
  • formic acid esters such as phenyl formate, pentafluoro oral benzaldehyde, Can indicate oxazole and the like.
  • Examples of the additive include inorganic acids such as sulfuric acid, organic acids such as formic acid, porohydrides such as sodium mupohydride, sodimucyanopolohydride, boronic acid, lithium hydride, etc. Aluminum or the like can be shown.
  • the reaction temperature may be appropriately selected from 120 ° C to the reflux temperature of the solvent to be used, and the reaction time may be appropriately selected within the range of several minutes to 96 hours.
  • a compound represented by the general formula (55) can be produced by reacting the compound represented by the general formula (54) according to the conditions described in 2- (ii) above.
  • the compound represented by the general formula (56) By reacting the compound represented by the general formula (55) with the compound represented by the general formula (20) according to the conditions described in the above 1_ (i), the compound represented by the general formula (56) Can be manufactured.
  • the compound represented by the general formula (54) is converted into a compound represented by the general formula (20) according to the conditions using the condensing agent described in 1) (i) above or the conditions using the mixed acid anhydride method. By reacting, the compound represented by the general formula (56) Can be manufactured.
  • the target product may be isolated from the reaction system according to a conventional method after completion of the reaction. If necessary, recrystallization, column chromatography, distillation, etc. It can purify by performing operation of. It is also possible to use the next reaction step without isolating the desired product from the reaction system.
  • Tables 1 to 4 show typical compounds represented by the general formula (1) or the general formula (5) having an insecticidal action, but the present invention is not limited thereto. It is not a thing.
  • n- represents normal
  • Me represents methyl group
  • E t represents ethyl group
  • n_P r represents normal propyl group
  • i_P r represents isopropyl.
  • Pill group “n _B u” is a normal butyl group
  • i _B u is an isobutyl group
  • s _B u is a secondary butyl group
  • t _B u” is a tertiary butyl group
  • H represents a hydrogen atom
  • "0” represents an oxygen atom
  • S represents a sulfur atom
  • C represents a carbon atom
  • N represents a nitrogen atom
  • F represents a fluorine atom
  • CI is a chlorine atom
  • a" B r is a bromine atom
  • an I an iodine atom
  • CF 3 is intended to represent each a triflate Ruo b
  • Phen-5-ylsafropropoxy phenyl benzothiophene-2,6-dibromo-4- (1,1,2,3,3,3-hexyl)
  • Table 5 shows the physical property values of the compounds represented by the general formula (1) or the general formula (5).
  • the 1 H-NMR shift values shown here use tetramethylsilane as the internal reference material.
  • opterus pruni Alaska lip aphid (Lipaphis erysimi) Kikuhimehi Kenaka, Framushi (Macrosiphoniel la sanborni) Chuilip Hikenaka / 1 Aphid (Macrosiphum euphorbiae) Broad bean aphid (Megoura cr ass i cauda) la Aphids (Myzus mal isuctus), aphids (Myzus mumecola), peach aphids (Myzus persicae) leeks, aphids (Neotoxoptera formosana), ringworms (Ovatus mal icolens), husubirea aphids (hum) Ropealosiphum padi, Rhalosiphum ruf i abdominal is, Sappaph is piri, Schizaphis pi r icola Mugihi 7 "Sitobion akebiae Beard aphid (Sitobion
  • Gr iocer is quatuordec i mpunctata Inequia / Donacia provost u Zorelli / Linaeidea aenea, Luperomorpha tunebrosa Idythia nig robi Oedema oryzae, P agr ia signata Evening, Icon / Phaedon brass icae Phyl lotreta str iolata Colorado / ⁇ pti notarsa decern I i neata), Corn root worms (Diabrotica sp.), Involv ulus cupreus, Rhynchites heros, A Gylas formicar ius, Anthonomus pomor
  • TTYSANOPTERA includes: Asaphothr i ps obs curus, Ghirothrips manicatus, Dendrothr ips minowai, Frankl iniel la i ntonsa), Frankl iniel la I i ivora, Hei iothr ips haemorrhoidal is, Cosmos thumma (Microcephalothr ips abd ominal is) Pseudodendrothr ips mori, Sci rtothr ips dorsal is, Selenothrips rubrocinctus, Inazamuma (S ten chaetothr ips biformis), Thr ips al I iorum, Thrips coloratus, Thr ips flavus, Thr ips hawai i ens is Black 7 "Hana Thr ips nigropi losus), Thrips palmi, Frankl inel la occidental is, Thr Thr
  • German cockroach (Blattel la germanica), Japanese cockroach (Blattel la I itur icol I is), Japanese black clover (Homorocoryphus jezoensis), Chinese crested (Homoro coryphus I i neosus) Kera (Gry I lota I pa sp.) Oxya hyla intr ica ta), ko / okusai, inako, (Oxya yezoensis), ⁇ Nosama / ku, nta (Locusta migrator ia), etc.
  • Diptera includes the following: Tipula aino, Bradysia agrestis, Izsatama /, Asphondyl ia sp., Dacus cucurbitae, Mikan Komi ((Dacus dorsal is), mandarin orange (Dacus tsuneonis) ⁇ ⁇ " ⁇ ⁇ ⁇ / Rhacochlaena japonica, Hydrel I ia gr iseola, Hydrel I ia sasa ki i, Drosophi la suzuki i, G hlorops oryzae, Meromyza nigr iventr is Rice, / ⁇ 7 Agromyza oryzae, Namok, Reno (Ghromatomyia horticola) Eggplant / ⁇ Mo ⁇ 7 reno (e (Li r iomyza bryoniae) Leek / ⁇ ⁇ 7 renoque (Li
  • Tylenchulus semi penetrans Aphe I enchus avenae, etc.
  • DORYLAIMIDA Longidorus martini, Longidorus sp.
  • Xiphinema amer icanum Xiphinema sp.
  • Arthropod lip limbs GIL0P0DA
  • Geji Thereuronema tuberculata
  • Arthropod double legs As a class (DI PLOPODA), for example, Ox i dus grac ilis, and as a mollusk (MOLL USCA), for example, slug (I nc il ar iabi I i neata).
  • the content of the compound effective for controlling pests in the insecticidal composition of the present invention is usually 0.5 to 20% by weight in powder, 5 to 50% by weight in emulsion, and 10 to 10 in wettable powder. 90% by weight, 0.1 to 20% by weight for granules and 10 to 90% by weight for flowable formulations.
  • the amount of carrier in each dosage form is usually 60 to 99% by weight for powders, 40 to 95% by weight for emulsions, 10 to 90% by weight for wettable powders, and 80 to 90% for granules. 9 to 9% by weight, and 10 to 90% by weight for flowable formulations.
  • the amount of adjuvant is 0 in the normal powder.
  • 1-2 0 wt%, 1 to the emulsion 2 0 weight 0/0, 0 with a wettable powder. 1 2 0 weight 0/0, the granules 0.1 to 20 weight 0 / o and 0.1 to 20 weight percent for flowable formulations.
  • the insecticidal composition of the present invention By applying the insecticidal composition of the present invention to a crop of an agricultural plant, it is possible to control pests generated during storage of the crop. That is, the insecticidal composition of the present invention as it is, or appropriately diluted with water or the like, or suspended in an amount effective for pest control in the form of agricultural plant crops or agricultural plant harvests.
  • post-harvest treatment such as spraying, smearing, application, dipping, powder coating, fumigation, smoke injection, or pressurized injection may be performed.
  • Agricultural plant crops include, for example, rice, barley, wheat, corn, rye, oats, endou, green beans, cowpeas, salta beans, saltapia beans, butter beans, pegiya beans, white beans, Lima beans, broad beans, soybeans, red beans, apricots, plums, sweet potatoes, plums, nectarine, peaches, oranges, grapefruits, natsum, mandarin oranges, sudachi, daidai, force pos, lime, lemon, bean paste, quince, apples, pears , Pear, apogado, kiwi fruit, guava, date palm, pineapple, passion fruit, banana, papaya, mango, strawberry, cranberry, hackleberry, blackberry, bullberry, oyster, watermelon, grape, cucumber, Melon, turnip, cauliflower , Cabbage, Japanese radish, Chinese cabbage, Komatsuna, watercress, keel, horseradish rust,
  • insecticidal composition of the present invention By applying the insecticidal composition of the present invention to plant seeds, it is possible to control pests that occur during the preservation of plant seeds (see dstorage).
  • the insecticidal composition of the present invention is sprayed and smeared on the plant seed or the plant seed storage site in an amount effective for pest control as it is, or appropriately diluted with water or suspended. Applying, dipping, powdering or smoking • Fumigation may be performed.
  • insecticidal composition of the present invention By applying the insecticidal composition of the present invention to plant seeds, it is possible to prevent damage caused by pests generated in the plant after sowing. That is, the insecticidal composition of the present invention is sprayed, smeared, soaked or dressed in an amount effective for controlling pests as it is, or appropriately diluted with water or the like, or suspended. By treating, plant seeds may be contacted with a compound effective for controlling pests.
  • Plant seeds refer to those that store nutrients for germination of young plants and are used for agricultural reproduction.
  • seeds such as corn, soybeans, red beans, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, green peas, capocha, sugar cane, tobacco, piman and black apricots
  • seeds such as potato, sweet potato, and konnyaku, edible lily, and seed balls such as bulbs such as tulips.
  • These plant seeds may be transformed. What is a transformed plant? A plant that is created by artificial manipulation of genes, etc., and does not exist in nature. Examples include soybean, corn, cotton, etc. that have been given herbicide resistance, corn, cotton, potato, etc., that have been given the ability to produce insecticides, such as rice and tobacco adapted to cold regions.
  • the dilution factor is appropriately selected depending on the target crop and insect damage, but is usually selected from the range of 1 to 100 times.
  • the amount used when dressing, spraying and smearing plant seeds is usually about 0.05 to 5% of the dry plant seed weight. These ranges are not limited, and may vary depending on the form of the preparation and the type of plant species to be treated.
  • the insecticidal composition of the present invention is formulated and used in a convenient form in accordance with a conventional formulation method for agricultural and horticultural agents. That is, these are mixed in a suitable inert carrier, or if necessary, together with an auxiliary agent in an appropriate ratio, dissolved, separated, suspended, mixed, impregnated, adsorbed or adhered, and an appropriate dosage form, for example, It can be formulated into suspensions, emulsions, solutions, wettable powders, granules, powders, tablets and the like.
  • the inert carrier may be either solid or liquid.
  • materials that can be used as the solid inert carrier include soybean flour, cereal flour, wood flour, bark flour, saw flour, and tobacco.
  • a material that can be a liquid inert carrier in addition to having a solvent ability itself, a compound effective for controlling pests can be dispersed with the aid of an auxiliary agent without having a solvent ability.
  • the following carriers can be exemplified as representative examples, and these are used alone or in the form of a mixture of two or more, for example, water, alcohols (for example, methanol, ethanol).
  • auxiliary agents the following typical auxiliary agents can be mentioned, and these auxiliary agents are used depending on the purpose, and are used alone or in combination with two or more auxiliary agents. However, in some cases, it is possible to use no adjuvant at all.
  • Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting compounds effective in controlling pests, such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, Polyoxyethylene higher fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkyl aryl sulfonate, naphthalene sulfonate, lignin sulfonate, higher Surfactants such as alcohol sulfates can be indicated.
  • adjuvants such as casein, gelatin, starch, Adjuvants such as methylcellulose, carboxymethylcellulose, arabic gum, polyvinyl alcohol, pine oil, coconut oil, bentonite, xanthan gum, lignin sulfonate can be used.
  • the following adjuvants may be used, and for example, adjuvants such as waxes, stearates and alkyl phosphates may be used.
  • adjuvants such as waxes, stearates and alkyl phosphates
  • auxiliary agents such as naphthalene sulfonic acid condensate and condensed phosphate can be used.
  • antifoaming agent for example, an auxiliary agent such as silicone oil can be used.
  • the insecticidal composition of the present invention is stable to light, heat, oxidation, etc., but if necessary, an antioxidant or an ultraviolet absorber such as BHT (2,6-di-t_peptide_4 _Methylphenol), phenol derivatives such as BHA (butyl hydroxyanisole), bisphenol derivatives, phenyl mono-naphthalamine, phenyl S-naphthylamine, condensates of phenetidine and acetone, or benzophenone series By adding an appropriate amount of compounds as stabilizers, a more stable composition can be obtained.
  • BHT 2,6-di-t_peptide_4 _Methylphenol
  • phenol derivatives such as BHA (butyl hydroxyanisole)
  • bisphenol derivatives such as BHA (butyl hydroxyanisole)
  • bisphenol derivatives such as BHA (butyl hydroxyanisole)
  • bisphenol derivatives such as BHA (butyl hydroxyanisole)
  • N-(4 _Heptafluoroisopropyl _ 2-methylsulfonylphenyl) _N_Methyl 3_Nitrobensamide 0.93 g, stannous chloride (anhydrous) 1. 40 g added to ethanol 2 Om I Then, 2 ml of concentrated hydrochloric acid was added dropwise. After charging, the temperature was raised to 60 ° C., stirred for 1.5 hours, and the reaction solution was poured into ice water. After neutralizing with potassium carbonate and adding ethyl acetate, the precipitated insoluble matter was filtered off using celite. The filtrate on the celite was washed well with ethyl acetate.
  • 3_ (Benzylamino) -2,6-difluorobenzoic acid was prepared according to the conditions described in Example 3_1 using 3-amino-1,2,6-difluorobenzoic acid, and then described in Example 3-2.
  • 3_ (Benzylamino) -2,6-difluorobenzoic acid chloride was prepared according to the conditions described in Example 3-3 using 4_heptafluoroloypropyl-1-methylaniline, and the title compound was Manufactured.

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  • Life Sciences & Earth Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pretreatment Of Seeds And Plants (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyrrole Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Furan Compounds (AREA)
  • Pyrane Compounds (AREA)

Abstract

L'invention concerne : une composition insecticide pour une graine de plante ou une culture ; et un nouveau procédé pour contrôler un insecte nuisible dans une graine de plante ou une culture récoltée à partir d'une plante agricole à l'aide de la composition insecticide. L'invention concerne spécifiquement : une composition insecticide comprenant un composé représenté par la formule générale (1) ou (5) en tant qu'ingrédient actif ; et un procédé pour contrôler un insecte nuisible, qui est caractérisé par l'application de la composition insecticide à une graine de plante ou à une culture récoltée à partir d'une plante agricole. (1) (5)
PCT/JP2007/001424 2006-12-19 2007-12-19 Composition insecticide pour une graine végétale ou une culture et utilisation de celle-ci WO2008075465A1 (fr)

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JP2006340923A JP2010047480A (ja) 2006-12-19 2006-12-19 虫害の予防方法

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CN102993054A (zh) * 2012-10-24 2013-03-27 中化蓝天集团有限公司 苯甲酰胺类衍生物、其制备方法及应用
JP2015091901A (ja) * 2008-08-13 2015-05-14 三井化学アグロ株式会社 新規な化合物
EP2835366A4 (fr) * 2012-04-03 2015-10-14 Mitsui Chemicals Agro Inc Procédé de production d'un dérivé d'amide aromatique alkylé
US9394240B2 (en) 2008-08-13 2016-07-19 Mitsui Chemicals Agro, Inc. Method for producing amide derivative
EP3556744A1 (fr) 2013-12-23 2019-10-23 Syngenta Participations Ag Composés insecticides
CN112479996A (zh) * 2019-09-12 2021-03-12 上海济煜医药科技有限公司 吡啶氮氧化合物及其制备方法和用途

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EP2072501A1 (fr) * 2007-12-21 2009-06-24 Bayer CropScience AG Dérivés d'aminobenzamide en tant qu'agents utiles pour contrôler les parasites d'animaux
CN115868499A (zh) * 2022-12-12 2023-03-31 中农立华生物科技股份有限公司 一种含溴虫氟苯双酰胺的复配农用杀虫剂及其应用

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US9394240B2 (en) 2008-08-13 2016-07-19 Mitsui Chemicals Agro, Inc. Method for producing amide derivative
JP2015091901A (ja) * 2008-08-13 2015-05-14 三井化学アグロ株式会社 新規な化合物
US9890110B2 (en) 2008-08-13 2018-02-13 Mitsui Chemicals Agro, Inc. Method for producing amide derivative
WO2010090282A1 (fr) 2009-02-06 2010-08-12 アグロカネショウ株式会社 Dérivés de 3‑aminoxalylaminobenzamide et agents insecticides et miticides les contenant en tant que principe actif
US8541473B2 (en) 2009-02-06 2013-09-24 Agro-Kanesho Co., Ltd. 3-aminoxalyl-aminobenzamide derivatives and insecticidal and miticidal agents containing same as active ingredient
EP2835366A4 (fr) * 2012-04-03 2015-10-14 Mitsui Chemicals Agro Inc Procédé de production d'un dérivé d'amide aromatique alkylé
US9353046B2 (en) 2012-04-03 2016-05-31 Mitsui Chemicals Agro, Inc. Method for producing alkylated aromatic amide derivative
CN102993054A (zh) * 2012-10-24 2013-03-27 中化蓝天集团有限公司 苯甲酰胺类衍生物、其制备方法及应用
EP3556744A1 (fr) 2013-12-23 2019-10-23 Syngenta Participations Ag Composés insecticides
WO2021047622A1 (fr) * 2019-09-12 2021-03-18 上海济煜医药科技有限公司 Oxynitrure de pyridine, son procédé de préparation et son utilisation
CN112479996A (zh) * 2019-09-12 2021-03-12 上海济煜医药科技有限公司 吡啶氮氧化合物及其制备方法和用途
CN113906013A (zh) * 2019-09-12 2022-01-07 上海济煜医药科技有限公司 吡啶氮氧化合物及其制备方法和用途
CN112479996B (zh) * 2019-09-12 2023-05-26 上海济煜医药科技有限公司 吡啶氮氧化合物及其制备方法和用途
CN113906013B (zh) * 2019-09-12 2024-03-12 上海济煜医药科技有限公司 吡啶氮氧化合物及其制备方法和用途

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AR064401A1 (es) 2009-04-01
CL2007003717A1 (es) 2008-04-18

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