WO2008075453A1 - Composition de lutte contre les organismes nuisibles - Google Patents

Composition de lutte contre les organismes nuisibles Download PDF

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Publication number
WO2008075453A1
WO2008075453A1 PCT/JP2007/001347 JP2007001347W WO2008075453A1 WO 2008075453 A1 WO2008075453 A1 WO 2008075453A1 JP 2007001347 W JP2007001347 W JP 2007001347W WO 2008075453 A1 WO2008075453 A1 WO 2008075453A1
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group
alkyl
phenyl
atom
general formula
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PCT/JP2007/001347
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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 WO2008075453A1 publication Critical patent/WO2008075453A1/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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives

Definitions

  • the present invention relates to a novel pest control composition exhibiting excellent pest control action for controlling pests of crops in a labor-saving manner.
  • WO 2005/073 1 65 pamphlet describes an amide derivative and its use as an insecticide.
  • an object of the present invention is to provide a new pest control composition that can simultaneously control pests that cannot or cannot be controlled by insecticides, acaricides, or fungicides alone.
  • Patent Document 1 International Publication No. 2005/073 1 65 Pamphlet
  • Patent Document 2 International Publication No. 2003/008372 Pamphlet
  • Patent Document 3 International Publication No. 2005/042474 Pamphlet
  • Non-Patent Document 1 Pesticide Manual (T e P e s t i c i d e M a n u a l T h i r t e e n t h E d i t i o n
  • a combination of one or more compounds selected from the compounds represented by (1) and one or more compounds selected from known insecticides, known acaricides or known fungicides thus, the present inventors have found that a plurality of pests can be efficiently controlled, and have completed the present invention. That is, the present invention is as follows.
  • ⁇ 1 ⁇ 2 , ⁇ 3 , ⁇ 4 each independently represents a carbon atom, a nitrogen atom or an oxidized nitrogen atom,
  • R 1 R 2 each independently represents a hydrogen atom, a C 1 -C 4 alkyl group or a C 1 -C 4 alkyl carbonyl group,
  • G 1 G 2 are each independently an oxygen atom or a sulfur atom
  • X is a hydrogen atom, a halogen atom or a trifluoromethyl group
  • n is an integer of 0 to 4,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Heterocyclic group is a pyridyl group, a pyridine-N-oxide group, Pyrimidinyl, pyridazyl, birazyl, furyl, chenyl, oxazolyl, isoxazolyl, oxaziazolyl, thiazolyl, isothiazolyl, imidazolyl, triazolyl, pyrrolyl, pyrazolyl, or tetrazolyl Indicates.
  • the heterocyclic group here is a pyridyl group, a pyridine-N-oxide group, Pyrimidinyl, pyridazyl, birazyl, furyl, chenyl, oxazolyl, isoxazolyl, oxaziazolyl, thiazolyl, isothiazolyl, imidazolyl, triazolyl, pyrrolyl, pyrazolyl, or tetrazolyl
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Y is an optionally substituted C1-C4 alkoxy group, C1-C4 group alkoxy group, C1-C3 haloalkylthio group, C1-C3 haloalkylsulfinyl group or C1-C3 It indicates haloalkylsulfonyl two Le group, Upsilon 5 Ha androgenic atom, C 1-C4 alkyl group, C 1-C 4 haloalkyl group, C 1-C 4 alkoxy groups, C 1-C 4 haloalkoxy group, C 1- C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C 1 _C 3 haloalkylsulfonyl group or cyano group, Y 3 is C2—C
  • Upsilon 6, Upsilon 9 are each independently a halogen atom, C 1-C4 alkyl group, C 1-C 4 haloalkyl group, C 1-C4 alkoxy group, C 1-C4 halo alkoxy group, C 1 —C 3 alkylthio group, C 1—C 3 haloalkylthio group, C 1—C 3 alkyl sulfinyl group, C 1—C 3 haloalkyl sulfinyl group, C 1—C 3 alkyl sulfonyl group, C 1—C 3 haloalkyl sulfonyl group or indicates Shiano group
  • Upsilon 8 is C 1-C 4 haloalkoxy group, C2- C 6 Pas one Furuoroarukiru group, C 1-C 6 Pas one full O b alkylthio group, C 1 -C 6, A perfluoroalkylsulfinyl group, or a C1-C6 perfluor
  • an active ingredient one or more compounds selected from the compounds represented by the formula: and one or more compounds selected from known insecticides, known acaricides, or known fungicides are contained.
  • the pest control composition characterized by the above-mentioned.
  • ⁇ 1 ⁇ 2 , ⁇ 3 , ⁇ 4 are each independently a carbon atom, nitrogen atom or oxidized Nitrogen atom,
  • R 1 R 2 each independently represents a hydrogen atom, a C 1 -C 4 alkyl group or a C 1 -C 4 alkyl carbonyl group,
  • G 1 G 2 are each independently an oxygen atom or a sulfur atom
  • X is a hydrogen atom, a halogen atom or a trifluoromethyl group
  • n is an integer of 0 to 4,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, virazyl group, furyl group, chenyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group) Represents an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group, or a tetrazolyl group).
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy Si 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 3 alkylsulfonyl group, C 1—C 3 Haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group,
  • Y is an optionally substituted C1-C4 alkoxy group, C1-C4 group alkoxy group, C1-C3 haloalkylthio group, C1-C3 haloalkylsulfinyl group or C1-C3 It indicates haloalkylsulfonyl two Le group, Upsilon 5 Ha androgenic atom, C 1-C4 alkyl group, C 1-C 4 haloalkyl group, C 1-C 4 alkoxy groups, C 1-C 4 haloalkoxy group, C 1- C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, or ⁇ 3 represents C2—C 6 perfluoro
  • Upsilon 6, Upsilon 9 are each independently a halogen atom, C 1-C4 alkyl group, C 1-C 4 haloalkyl group, C 1-C4 alkoxy group, C 1-C4 halo alkoxy group, C 1 —C 3 alkylthio group, C 1—C 3 haloalkylthio group, C 1—C 3 alkyl sulfinyl group, C 1—C 3 haloalkyl sulfinyl group, C 1—C 3 alkyl sulfonyl group, C 1—C 3 haloalkyl sulfonyl group or indicates Shiano group
  • Upsilon 8 is C 1-C 4 haloalkoxy group, C2- C 6 Pas one Furuoroarukiru group, C 1-C 6 Pas one full O b alkylthio group, C 1 -C 6, A perfluoroalkylsulfinyl group, or a C1-C6 perfluor
  • ⁇ 2 and ⁇ 4 are hydrogen atoms
  • ⁇ 3 is a heptafluoroisopropyl group
  • ⁇ 5 is a bromine atom
  • X is a hydrogen atom
  • G 2 is an oxygen atom
  • R 2 is a hydrogen atom
  • R 1 R 2 When one of R 1 R 2 is a hydrogen atom, the other is a C 1 _C4 alkyl group or a C 1—C 4 alkylcarbonyl group, or both are C 1—C4 An alkyl group or a C 1 _C 4 alkylcarbonyl group,
  • G 1 G 2 are each independently an oxygen atom or a sulfur atom
  • X 1 X 2 , X 3 and X 4 are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, virazyl group, furyl group, chenyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group) Represents an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group, or a tetrazolyl group).
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1_C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano
  • Y represents a C 1-C 3 haloalkylthio group, C 1-C 3 haloalkylsulfenyl Finiru group or C 1-C 3 haloalkylsulfonyl two Le group
  • Upsilon 5 is halogen atom, C 1-C4 alkyl Group, C1-C4 haloalkyl group, C1-C4 alkyloxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkyl Sulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1 —C 3 haloalkylsulfonyl group, or cyan group
  • ⁇ 3 is a C2—C6 perfluoroalkyl group, C 1— C 6 perfluor
  • ⁇ 6 and ⁇ 9 are each independently a halogen atom, C 1 -C 4 alkyl Group, C1-C4 haloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1—C 3 haloalkylsulfonyl group, or cyan group
  • Y 8 is C 1—C 4 haloalkoxy group, C2 — C 6 perfluoroalkyl group, C 1—C 6 perfluoroalkylthio group, C 1 —C 6 perfluoroalkylsulfinyl group, or C 1—C 6 perfluoroalkylsulf
  • Y 6 and ⁇ 9 always represents a C 1 -C 3 haloalkylthio group, a C 1 -C 3 haloalkylsulfinyl group or a C 1 _C 3 haloalkylsulfonyl group.
  • Upsilon 5 is halogen atom, C 1-C4 alkyl Group, C1-C4 haloalkyl group, C1-C4 alkyloxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkyl sulfinyl group, a C 1-C 3 haloalkylsulfinyl group, C 1-C 3 alkylsulfonyl group, C 1 -C 3 haloalkylsulfonyl group or Shiano group,
  • Upsilon 3 is C2- C6 Pas one Furuoroarukiru group, C 1- C 6 perfluor
  • the compound represented by the general formula (1) is a compound represented by the general formula (1 a), wherein is a phenyl group,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • R 1 R 2 each independently represents a hydrogen atom, a C 1 -C 4 alkyl group or a C 1 -C 4 alkyl carbonyl group,
  • G 1 G 2 are each independently an oxygen atom or a sulfur atom
  • X 1 X 2 , X 3 and X 4 are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Heterocyclic group (wherein the heterocyclic group is a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a birazyl group, a furyl group, a enyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group) , Iso A thiazolyl group, an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group, or a tetrazolyl group; Or
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Y represents a C 1-C 3 haloalkylthio group, C 1-C 3 haloalkylsulfenyl Finiru group or C 1-C 3 haloalkylsulfonyl two Le group
  • Upsilon 5 is halogen atom, C 1-C4 alkyl Group, C1-C4 haloalkyl group, C1-C4 alkyloxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkyl Sulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1 —C 3 haloalkylsulfonyl group, or cyan group
  • ⁇ 3 is a C2—C6 perfluoroalkyl group, C 1— C 6 perfluor
  • Upsilon 6, Upsilon 9 are each independently a halogen atom, C 1-C4 alkyl group, C 1-C 4 haloalkyl group, C 1-C4 alkoxy group, C 1-C4 halo alkoxy group, C 1 —C 3 alkylthio group, C 1—C 3 haloalkylthio group, C 1—C 3 alkyl sulfinyl group, C 1—C 3 haloalkyl sulfinyl group, C 1—C 3 alkyl sulfonyl group, C 1—C 3 haloalkyl sulfonyl group or indicates Shiano group
  • Upsilon 8 is C 1-C 4 haloalkoxy group, C2- C 6 Pas one Furuoroarukiru group, C 1-C 6 Pas one full O b alkylthio group, C 1 -C 6, A perfluoroalkylsulfinyl group, or a C1-C6 perfluor
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1_C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Y represents a C 1-C 3 haloalkylthio group, C 1-C 3 haloalkylsulfenyl Finiru group or C 1-C 3 haloalkylsulfonyl two Le group
  • Upsilon 5 is halogen atom, C 1-C4 alkyl Group, C1-C4 haloalkyl group, C1-C4 alkyloxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkyl Sulfinyl group, C 1— C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1 —C 3 haloalkylsulfonyl group, or cyan group
  • Y 3 is C2—C6 perfluoroalkyl group, C 1—C 6 perfluoro group
  • R 1 R 2 each independently represents a hydrogen atom, a C 1 -C 4 alkyl group or a C 1 -C 4 alkyl carbonyl group,
  • G 1 G 2 are each independently an oxygen atom or a sulfur atom
  • X 1 X 2 , X 3 and X 4 are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, virazyl group, furyl group, chenyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group) Represents an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group, or a tetrazolyl group).
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Y represents a C 1 -C 3 haloalkylthio group, a C 1 -C 3 haloalkylsulfinyl group or a C 1 -C 3 haloalkylsulfonyl group
  • ⁇ 5 represents a fluorine atom, a chlorine atom, an iodine atom, C1-C4 alkyl group, C1-C4 haloal Kill group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkyl group sulfinyl groups, C 1-C3 alkyl Rusuruhoniru group, a C 1 _C 3 haloalkylsulfonyl group or Shiano group
  • Y 3 is
  • Upsilon 6, Upsilon 9 are each independently a halogen atom, C 1-C4 alkyl group, C 1-C 4 haloalkyl group, C 1-C4 alkoxy group, C 1-C4 halo alkoxy group, C 1 —C 3 alkylthio group, C 1—C 3 haloalkylthio group, C 1—C 3 alkyl sulfinyl group, C 1—C 3 haloalkyl sulfinyl group, C 1—C 3 alkyl sulfonyl group, C 1—C 3 haloalkyl sulfonyl group or indicates Shiano group
  • Upsilon 8 is C 1-C 4 haloalkoxy group, C2- C 6 Pas one Furuoroarukiru group, C 1-C 6 Pas one full O b alkylthio group, C 1 -C 6, A perfluoroalkylsulfinyl group, or a C1-C6 perfluor
  • the compound represented by the general formula (1) is a compound represented by the general formula (1 a), wherein is a phenyl group,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2- C4 alkenyl group, C2_C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, C1- C3 alkoxy group, C 1—C3 haloalkoxy group, C 1—C 3 alkylthio group, C 1—C 3 haloalkylthio group, C 1—C 3 alkyl sulfinyl group, C 1—C 3 haloalkyl sulfinyl group, C 1— C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Y represents a C 1 _C 3 haloalkylthio group, a C 1-C 3 haloalkylsulfinyl group or a C 1-C 3 haloalkylsulfonyl group
  • Y 5 represents a fluorine atom, a chlorine atom, an iodine atom, C 1—C4 alkyl group, C 1—C4 haloalkyl group, C 1—C4 alkoxy group, C 1—C 4 haloalkoxy group, C 1—C 3 alkylthio group, C 1—C 3 haloalkylthio group, C 1— C3 Arukirusu Rufiniru group, C 1-C 3 haloalkylsulfinyl group, C 1-C3 alkyl Rusuruhoniru group, a C 1 _C 3 haloalkylsulfonyl group or Shiano group,
  • Y 3 is C 2-C 6 Pas one Fur
  • R 1 R 2 each independently represents a hydrogen atom, a C 1 -C 4 alkyl group or a C 1 -C 4 alkyl carbonyl group,
  • G 1 G 2 are each independently an oxygen atom or a sulfur atom
  • X 1 X 2 , X 3 and X 4 are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy Si 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, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyan
  • Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, virazyl group, furyl group, chenyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group) Represents an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group, or a tetrazolyl group).
  • Halogen atom C 1—C 4 alkyl group, C 1—C 4 haloalkyl group, C 2—C 4 alkenyl group, C 2—C 4 haloalkenyl group, C 2—C 4 alkynyl group, C 2—C 4 halo Alkynyl, C 3— C 6 cycloalkyl, C 3— C 6 halocycloalkyl, C 1—C 3 alkoxy, C 1—C 3 haloalkoxy, C 1—C 3 alkylthio, C 1— C3-haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3-haloalkylsulfinyl group, C1-C3-alkylsulfonyl group, C1-C3-haloalkylsulfonyl group, amino group, C1-C 4-alkylamino group, di-C1-C4-alkylamino group, cyan
  • Y represents a C2- C3 haloalkylthio group, C 1-C 3 haloalkylsulfenyl Finiru group or C 1-C 3 haloalkylsulfonyl two Le group
  • Upsilon 5 is halogen atom, C 1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkyloxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group , C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1 —C 3 haloalkylsulfonyl group, or cyan group
  • ⁇ 3 is a C2—C6 perfluoroalkyl group, C 1—C 6 A per
  • Upsilon 6, Upsilon 9 are each independently a halogen atom, C 1-C4 alkyl group, C 1-C 4 haloalkyl group, C 1-C4 alkoxy group, C 1-C4 halo alkoxy group, C 1 —C 3 alkylthio group, C 2—C 3 haloalkylthio group, C 1—C 3 alkyl sulfinyl group, C 1—C 3 haloalkyl sulfinyl group, C 1—C 3 alkyl sulfonyl group, C 1—C 3 haloalkyl sulfonyl group or indicates Shiano group
  • Upsilon 8 is C 1-C 4 haloalkoxy group, C2- C 6 Pas one Furuoroarukiru group, C 1-C 6 Pas one full O b alkylthio group, C 1 -C 6, Perfluoroalkylsulfinyl group, or C 1—C 6 perfluorin
  • Y 6 and ⁇ 9 always represents a C 2 -C 3 haloalkylthio group, a C 1 -C 3 haloalkylsulfinyl group, or a C 1 _C 3 haloalkylsulfonyl group.
  • the compound represented by the general formula (1) is a compound represented by the general formula (1 a), wherein is a phenyl group,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Y represents a C2- C3 haloalkylthio group, C 1-C 3 haloalkylsulfenyl Finiru group or C 1-C 3 haloalkylsulfonyl two Le group
  • Upsilon 5 is halogen atom, C 1-C4 alkyl group, C1-C4 haloalkyl group, C1-C4 alkyloxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group , C 1—C 3 haloalkylsulfinyl group, C 1—C 3 alkylsulfonyl group, C 1 —C 3 haloalkylsulfonyl group, or cyan group
  • ⁇ 3 is a C2—C6 perfluoroalkyl group, C 1—C 6 A per
  • the compound represented by the general formula (1) is a compound of the general formula (1) in which A 1 A 2 , A 3 and A 4 are each independently a carbon atom, nitrogen atom or oxidized Indicates a nitrogen atom,
  • R 1 R 2 When either one of R 1 R 2 is a hydrogen atom, the other is a C 1 _C4 alkyl group or a C 1—C 4 alkylcarbonyl group, or both are a C 1—C4 alkyl group or C 1 _C 4 An alkylcarbonyl group,
  • G 1 G 2 are each independently an oxygen atom or a sulfur atom
  • X is a hydrogen atom, a halogen atom or a trifluoromethyl group
  • n is an integer of 0 to 4
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, virazyl group, furyl group, chenyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group) Represents an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group, or a tetrazolyl group).
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Y represents a optionally substituted C 1-C 4 alkoxy groups or C 1 -C 4 haloalkoxy groups
  • Upsilon 5 is halogen atom, C 1-C4 alkyl group, C 1-C4 haloalkyl group C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3-alkylsulfinyl group, C1-C3-haloalkylsulfinyl group, C 1-C 3 alkylsulfonyl group, C 1-C 3 haloalkylsulfonyl group, or cyano group
  • Y 3 represents C 2 -C 6 perfluoroalkyl group, C 1 -C 6 perfluoroalkylthio group, C 1 _C 6 perfluoroalkylsulfinyl group, or C 1—C
  • Upsilon 6, Upsilon 9 are each independently a halogen atom, C 1-C4 alkyl group, C 1-C 4 haloalkyl group, C 1-C4 alkoxy group, C 1-C4 halo alkoxy group, C 1 —C 3 alkylthio group, C 1—C 3 haloalkylthio group, C 1—C 3 alkyl sulfinyl group, C 1—C 3 haloalkyl sulfinyl group, C 1—C 3 alkyl sulfonyl group, C 1—C 3 haloalkyl
  • a sulfonyl group or a cyano group, ⁇ 8 is a C 1—C 4 haloalkoxy group, C 2—C 6-perfluoroalkyl group, C1-C6-perfluoroalkylthio group, C1-C6-perfluoroalkylsulfinyl group, or C1-C6-
  • R ⁇ or R 2 is a hydrogen atom
  • the other is a C 1 _C4 alkyl group or a C 1 —C 4 alkylcarbonyl group, or both are a C 1 —C4 alkyl group or C 1 _C 4 alkyl carbonyl group,
  • G 1 G 2 are each independently an oxygen atom or a sulfur atom
  • X 1 X 2 , X 3 and X 4 are each independently a hydrogen atom, a halogen atom or a trifluoromethyl group,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group Group, C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C 3-haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3-haloalkylsulfinyl group, C1-C3-alkylsulfonyl group, C1-C3-haloalkylsulfonyl group, amino group, C1-C4 Alkylamino group, di-C1-C4 alkylamino group,
  • Heterocyclic group (wherein the heterocyclic group is pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, virazyl group, furyl group, chenyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group) Represents an isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group, or a tetrazolyl group).
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Y represents a optionally substituted C 1-C4 haloalkoxy group
  • Upsilon 5 is halogen atom, C 1-C4 alkyl group, C 1-C 4 haloalkyl group, C 1 -C4 alkoxy group, C1-C4 haloalkoxy group, C1-C3 alkylthio group Group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, or cyano group
  • Y 3 represents C 2—C 6 perfluoroalkyl group, C 1—C 6 perfluoroalkylthio group, C 1—C 6 perfluoroalkylsulfinyl group, or C 1—C6 Represents a fluoroalky
  • the compound represented by the general formula (1) is a compound represented by the general formula (1 a), wherein is a phenyl group,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, C 1— C 3 alkylsulfinyl group, C 1 —C 3 haloalkylsulfinyl group, C 1 —C 3 alkylsulfonyl group, C 1 —C 3 haloalkylsulfonyl group, amino group, C 1 —C 4 alkylamino group, di C 1 — C4 alkylamino group
  • Known insecticides known acaricides or known fungicides are azinphos methyl, acephete, isoxathion, isofenphos, etion, etrimphos, oxidimethone.methyl, oxydeprophos, quinalphos, chlorpyrifos, chlorpyrifosmethyl, chlorfen Vinfos, Cianofos, Dioxabenzophos, Dichlorpos, Disulfoton, Dimethylvinphos, Dimethoate, Sulprofos, Diazinon, Thiometone, Tetrachlorbinphos, Temefos, Tebupyrimfos, Terbufos, Naretodo, Bamidothione, Virafenthiofos , Pyrimifosmethyl, fenitrothion, fenchione, phentoate, fencerfothion, flupirazophos, prothiofos, propopas, Lofenofo
  • R 51 represents a methyl group or a chloro group
  • R 52 represents a methyl group, a chloro group, a bromo group or a cyano group
  • R 53 represents a chloro group, a bromo group, a trifluoromethyl group or a cyanomethoxy group
  • R 54 represents a methyl group or an isopropyl group.
  • Triazimephone Hexaconazole, Propiconazol, Ibuconazol, Prochloraz, triflumizole, tebuconazole, epoxyconazole, diphenoconazole, flusilazol, triazimenol, cyproconazole, metconazol, fluquinconazol, vitertanol, tetraconazole, triconicol , Frutriafol, Penconazol, Diniconazozol, Fenbuconazol, Bromconazol, Imibenconazol, Shimeconazol, Microbutanyl, Himexazol, Imazaril, Frametovir, Tifluzazol, Etrizozol , Okispocona zool fumarate, Pefrazoate, Prothioconazole, Pyrifenox, Phenarimol, Nuarimol, Bupirimate, Mepanipyrim, Cyprodinil, Pyrimethanyl, Meta
  • R 11 represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an arylalkyl group or a heterocyclic alkyl group
  • R 1 2 and R 17 are each a hydrogen atom
  • R 1 3 and R 14 independently represent a hydrogen atom and an alkyl group having 1 to 6 carbon atoms
  • R 15 and R 16 each represent a hydrogen atom
  • R 18 represents an aryl group. Or represents a heterocycle.
  • R 21 is an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkenyl group having 2 to 6 carbon atoms substituted with halogen.
  • R22 and R27 each represent a hydrogen atom
  • R23 and R24 each independently represent a hydrogen atom
  • R25 and R26 each represent a hydrogen atom
  • R28 represents an aryl group or a heterocycle.
  • Known insecticides known acaricides or known fungicides are fenitrothion, fenthion, isoxathion, acephelate, buprofezin, pipropoxyphene, silafluophene, dinotefuran, imidacloprid, etofenprox, halfenprox, thiamethoxanthine, , Acetamiprid, nitenbiram, thiacloprid, benfuracarb, mesomil, phenobalp, spinosad, pimetrozine, chromafunozide, lepimectin, fipronil,
  • R 51 represents a methyl group or a chloro group
  • R 52 represents a methyl group, a chloro group, a bromo group or a cyano group
  • R 53 represents a chloro group, a bromo group or a trifluoro group. It represents Romechiru group or Shianome butoxy group
  • R 5 4 represents a methyl group or an isopropyl group.
  • Fenpyroximate pyridaben, hexithiazox, fenbutasoxide, tebufenvirad, pyrimidifen, etoxazol, polynactin complex, milbemectin, acequinosyl, bifenase, spirodiclofen, dienochlor, spiromefene, cloromephene Tolfenvirad, flucacrylim, propargite, difenthiuron, fluefenoxuron, penthiovirad, fursulfamide, iminoctadine arbesylate, cibenzolral S methyl, ferrimzone, pyroxylone, olisastrobin, azoxystrobin, carpropa Midi, Diclocimet, Probenazol, Thiazinyl, Isoprothiolane, Tricyclazol, Fusara , Kasugamycin, phenoxanyl, mepronil
  • R 11 represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an arylalkyl group or a heterocyclic alkyl group
  • R 1 2 and R 17 are each a hydrogen atom
  • R 1 3 and R 14 independently represent a hydrogen atom and an alkyl group having 1 to 6 carbon atoms
  • R 15 and R 16 each represent a hydrogen atom
  • R 18 represents an aryl group. Or represents a heterocycle.
  • R 21 is an alkyl group having 1 to 6 carbon atoms substituted with halogen, a cycloalkyl group having 3 to 6 carbon atoms substituted with halogen, or an alkenyl group having 2 to 6 carbon atoms substituted with halogen.
  • R22 and R27 each represent a hydrogen atom
  • R23 and R24 each independently represent a hydrogen atom
  • R25 and R26 each represent a hydrogen atom
  • R28 represents an aryl group or a heterocycle.
  • [1 7] The above [1 5], characterized by containing 0.001 to 95% by weight of one or more compounds selected from known insecticides, known acaricides, and known fungicides.
  • the pest control composition as described.
  • [1 8] A method for controlling pests, which comprises applying the pest control composition according to [17] to a pest or a habitat of the pest.
  • [0023] [19] A method for preventing damage by pests, comprising applying the pest control composition according to [17] to plant seeds.
  • [20] A method for preventing damage by pests, which comprises contacting the plant pests with the pest control composition according to [17].
  • the prevention method according to [20], wherein the method of contacting the plant seed is spraying treatment, smearing treatment, dipping treatment, or powdering treatment.
  • the plant seeds are corn, soybeans, red beans, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, sya-endu, capochia, sugar cane, tobacco, one-man and [19]
  • [0029] A method for preserving plant seeds, comprising applying the pest control composition according to [17] to plant seeds.
  • [0031] [27] A method for preserving a crop, which comprises applying the pest control composition according to [17] to a crop of an agricultural plant.
  • the application method to the harvest of agricultural plants is spraying treatment, smearing treatment, coating treatment, dipping treatment, powder coating treatment, fumigation / smoke treatment or pressurized injection [27] ]
  • the present invention it is possible to protect against a pest and a plurality of pests exhibiting drug resistance and the like for which a known pesticide, a known acaricide or a known fungicide alone did not provide a sufficient control effect. It is possible to provide a pest control composition that exhibits a remarkable control effect and has a remarkable control effect against a plurality of pests that exhibit pest control and drug resistance that could not be controlled by themselves. . Therefore, the pest control composition of the present invention can greatly contribute to the labor saving of agriculture.
  • N- means normal, "i-” means iso, “s_” means secondary, and "t-” means tertiary.
  • Halogen atom includes fluorine atom, chlorine atom, bromine atom or iodine atom.
  • C1_C3 alkyl group examples include linear or branched alkyl groups having 1 to 3 carbon atoms such as methyl, ethyl, n-propyl, i-propyl, and the like. ,
  • C 1 _C4 alkyl group examples include, in addition to the “C 1 _C3 alkyl group”, linear or branched chains such as n_ptyl, s_ptyl, i_ptyl, t_ptyl, and cyclopropylmethyl. And an alkyl group having 1 to 4 carbon atoms.
  • C 1 _C6 alkyl group examples include, in addition to “C 1 _C4 alkyl group", n-pentyl, 2_pentyl, 3_pentyl, neopentyl, n-hexyl, 2-hexyl, 4 Examples thereof include linear or branched alkyl groups having 1 to 6 carbon atoms such as _methyl_2_pentyl, 3_methyl_ ⁇ _pentyl, and cyclobutylmethyl.
  • Examples of the "C1-C3 haloalkyl group” include monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, bromo Difluoromethyl, 1_fluoroethyl, 2_fluoroethyl, 2, 2-difluoroethyl, 2, 2, 2_trifluoroethyl, 1_chloroethyl, 2_chloroethyl, 2,2-dichloroethyl, 2, 2, 2-Trichloroethyl, 1-Bromoethyl, 2-Bromoethyl, 2,2_Dibu-Methyl, 2,2,2-Tribromoethyl, 2-methyl ether, Pentafluoroethyl, 3_Fluoro-n-propyl, 3_Black _ n-propy
  • C1-C4 haloalkyl group for example, in addition to “C1-C3 haloalkyl group", 4_fluoro-n-butyl, 4_chloro_n_butyl, nonafluoro-n_butyl, nonafluoro- Examples thereof include a linear or branched alkyl group having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as 2_butyl.
  • C2_C4 alkenyl group examples include alkenyl groups having 2 to 4 carbon atoms having a double bond in a carbon chain such as vinyl, aryl, 2_butenyl, 3_butenyl and the like.
  • Examples of the "C 2 -C 4 haloalkenyl group” include 3,3-difluoro-2_propenyl, 3,3-dichroic 2_propenyl, and 3,3_dibromo-1_proenyl. May be the same or different, such as phenyl, 2,3_dibromo-1-propenyl, 4,4-difluoro_3-butenyl, 3,4,4_tribromo_3-butenyl, etc. Examples thereof include a straight chain or branched chain alkenyl group having 2 to 4 carbon atoms having a double bond in a carbon chain substituted by a mouth atom.
  • Examples of the "C2_C4 alkynyl group” include a straight chain having a triple bond in a carbon chain such as propargyl, 1-butyne_3_yl, 1-butyne-3_methyl_3-yl, etc. Examples include branched chain alkynyl groups having 2 to 4 carbon atoms.
  • Examples of the "C2-C4 haloalkynyl group” are 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 with one or more halogen atoms.
  • C3-C6 cycloalkyl group examples include carbon atoms having a cyclic structure such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl and the like having 3 to 6 carbon atoms. Cycloalkyl groups.
  • Examples of the "C3-C6 halocycloalkyl group” include the same or different, for example, 2, 2, 3, 3-tetrafluorocyclobutyl, 2_chlorocyclohexyl, 4_chlorocyclohexyl hexyl, etc. And a cycloalkyl group having 3 to 6 carbon atoms having a cyclic structure substituted with one or more halogen atoms.
  • C1-C3 alkoxy group examples include linear or branched alkoxy groups having 1 to 3 carbon atoms such as methoxy, ethoxy, n_propyloxy, and isopropyloxy. Is mentioned.
  • C1-C4 alkoxy group in addition to the "C1-C3 alkoxy group", for example, a linear or branched chain such as n_butyloxy, isoptyloxy, s_ptyloxy, t_butyloxy, etc. And an alkoxy group having 1 to 4 carbon atoms.
  • Examples of the "C1-C3 haloalkoxy group” include trifluoromethoxy, difluoromethoxy, monofluoromethoxy, pentafluoroethoxy, 1,1,1,3,3,3_hexafluoro-2-propyloxy, 2_Fluoroethoxy, 2,2-Difluoroethoxy, 2,2,2_Trifluoroethoxy, 2_Chloro ethoxy, 2,2-Dichloro ethoxy, 2,2,2-Trichloroethoxy, 3_ Fluoro-n-propyloxy, 2, 2, 3, 3-tetrafluoro-n-propyloxy, 2, 2, 3, 3, 3 _pentafluoro _n-propyloxy, 1,3-difluoro-2-propyloxy, 1 _ black 3_Fluoro-2_propyloxy, to 1, 1, 2, 3, 3, 3_ Xafluoropropyloxy, 2, 2, 2_trifluoro-1_trifluoro
  • the "C 1 -C 4 haloalkoxy group” includes, for example, 1, 1, 1, 1, 3, 3, 4, 4, 4-octafluoro-2-ptyloxy in addition to "C 1 -C 3 haloalkoxy group” And a linear or branched haloalkoxy group having 1 to 4 carbon atoms substituted with one or more halogen atoms which may be the same or different.
  • C1-C3 alkylthio group examples include linear or branched alkylthio having 1 to 3 carbon atoms such as methylthio, ethylthio, n-propylthio, i-propylthio, cyclopropylthio and the like. Groups.
  • C1-C4 alkylthio group for example, in addition to “C1-C3 alkylthio group”, for example, n_butylthio, i_ptylthio, s_butylthio, t-butylthio, cyclopropylmethylthio, etc. And an alkylthio group having 1 to 4 carbon atoms in the form of a straight chain or branched chain.
  • C1-C3 haloalkylthio group examples include trifluoromethylthio, pentafluoroethylthio, 2_fluoroethylthio, 2, 2, 2-trifluoroethylthio, Heptafluoro_n-propylthio, heptafluoro i-propylthio, 1, 1, 2, 3, 3, 3_hexafluoropropylthio, 2, 2, 2_trifluoro-1_trifluoromethylethylthio, Substituted with one or more halogen atoms, which may be the same or different, such as 2_trifluoromethyloxy-1,1,2,2-trifluoroethylthio, 1,1,2,2,2-tetrafluoroethylthio Examples thereof include a linear or branched alkylthio group having 1 to 3 carbon atoms.
  • Examples of the “C 1 -C 4 haloalkylthio group” include, in addition to “C 1 -C 3 haloalkylthio group”, for example, nonafluoro-n_ptylthio, nonafluoro-s — 1 or 4 linear or branched carbon atoms substituted with one or more halogen atoms, which may be the same or different, such as ptylthio, 4, 4, 4_trifluoro-n_ptylthio, etc. Of the alkylthio group.
  • 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. A number 1-3 alkylsulfinyl group is mentioned.
  • 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, 3, 3, 3 _Hexafluoropropylsulfinyl, 2, 2, 2_trifluoro-1 —trifluoromethylethylsulfinyl, 2 _trifluoromethoxy 1 , 1, 2_Trifluoroethylsulfinyl, 1, 1, 2, 2-tetrafluoroethylsulfinyl, etc., which may be the same or different, linear or branched chain substituted by one or more halogen atoms And an alkylsulfiny
  • 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. A few 1-3 alkylsulfonyl groups are mentioned.
  • C1-C3 haloalkylsulfonyl group examples include trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2, 2, 2_trifluoroethylsulfonyl, heptafluoro_n_propylsulfonyl, heptafluoro_ i-propylsulfonyl, 1,1,2,3,3,3_hexafluoropropylsulfonyl, 2,2,2_trifluoro- 1_trifluoromethylethylsulfonyl, 2_trifluoromethyloxy 1,1,2, _Trifluoroethylsulfonyl, 1,1,2,2,2-tetrafluoroethylsulfonyl And a linear or branched alkylsulfonyl group having 1 to 3 carbon atoms substituted with one or more halogen atoms which
  • C 1 -C 4 alkylamino group for example, methylamino, ethylamino, n-propylamino, i-propylamino, n_ptylamino, cyclopropylamino, 2, 2, 2_trifluoroethyl
  • alkylamino groups for example, linear, branched or cyclic alkylamino groups having 1 to 4 carbon atoms such as amino.
  • Examples of the "di-C1-C4 alkylamino group” include linear or branched carbon atoms which may be the same or different, such as dimethylamino, dimethylamino, N-ethyl-1-N-methylamino and the like. Examples include amino groups substituted by 1 to 4 alkyl groups.
  • Examples of the "C1-C4 alkylcarbonyl group” include linear, branched, or cyclic carbon atoms such as formyl, acetyl, propionyl, isopropyl-powered sulfonyl, cyclopropyl-powered sulfonyl, 1 to 4 carbon atoms.
  • An alkylcarbonyl group An alkylcarbonyl group.
  • Examples of the "C1-C4 haloalkylcarbonyl group” include, for example, fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, dichloroacetyl, trichloroacetyl, bromoacetyl, iodide acetyl, 3, 3, 3_Trifluoropropionyl, 2,2,3,3,3_Pentafluorine Propionyl, etc. may be the same or different and the number of linear or branched carbon atoms substituted by one or more halogen atoms 1 Up to 4 alkyl strengths include a sulfonyl group.
  • Examples of the "C 1 -C 4 alkyl carbonyloxy group” include linear or branched alkyl carbonyloxy groups having 1 to 4 carbon atoms such as acetoxy and propionyloxy. .
  • Examples of the "C1-C4 alkoxycarbonyl group” include a straight-chain group such as methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl, and the like. Or a branched alkoxycarbonyl group having 1 to 4 carbon atoms.
  • Examples of the "C 1 -C 4 perfluoroalkyl group” include trifluoromethyl, pentafluoroethyl, heptafluoro_n-propyl, heptafluoro i-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, Nonafluoro-i — linear or branched alkyl groups having 1 to 4 carbon atoms, all substituted with fluorine atoms such as ptyl.
  • C 2 -C 6 perfluoroalkyl group means, for example, pentafluoroethyl, heptafluoro_n-propyl, heptafluoro 1-propyl, nonafluoro-n-butyl, nonafluoro-2-butyl, nonafluoro i-Butyl, perfluoro-n-pentyl, perfluoro-n-hexyl, etc., linear or branched alkyl groups having 2 to 6 carbon atoms, all substituted with fluorine atoms. It is done.
  • Examples of the "C 1 -C 6 perfluoroalkylthio group" include trifluoromethylthio, pentafluoroethylthio, heptafluoro_n-propylthio, heptafluoro mouthpiece i-propylthio, nonafluoron-butylthio, Nonafluoro-2-ptylthio, nonafluoro-i-ptylthio, perfluoro mouth n-pentylthio, perfluoro-n-hexylthio, etc. Linear or branched carbon atoms all substituted by fluorine atoms 1-6 An alkylthio group.
  • C 1 -C 6 perfluoroalkylsulfinyl group examples include trifluoromethylsulfinyl, pentafluoroethylsulfinyl, heptafluoro_n-propylsulfinyl, heptafluor mouthpiece i-propyls Linear, all substituted with fluorine atoms such as rufinyl, nonafluoro-n-butylsulfinyl, nonafluoro-2-butylsulfinyl, nonafluoro-i-butylsulfinyl, perfluoro-n-pentylsulfinyl, perfluoro-n-hexylsulfinyl Alternatively, branched alkylsulfinyl groups having 1 to 6 carbon atoms can be mentioned.
  • Examples of the "C 1 -C 6 perfluoroalkylsulfonyl group” include trifluoromethylsulfonyl, pentafluoroethylsulfonyl, heptafluoro n_propylsulfonyl, heptafluor mouth i-propylsulfonyl, Linear or branched, all substituted by fluorine atoms such as nonafluoro-n_ptylsulfonyl, nonafluoro-2-butylsulfonyl, nonafluoro-i-butylsulfonyl, perfluoro-n-pentylsulfonyl, perfluoro-n-hexylsulfonyl Examples include chain-like alkylsulfonyl groups having 1 to 6 carbon atoms.
  • the compounds represented by the general formula (1) and the general formula (1a) may contain one or a plurality of asymmetric carbon atoms or asymmetric centers in the structural formula.
  • the compounds represented by the general formula (1) and the general formula (1a) include all the optical isomers and mixtures containing them in an arbitrary ratio. It is included.
  • the compounds represented by the general formula (1) and the general formula (1a) may have two or more geometric isomers derived from a carbon-carbon double bond in the structural formula.
  • the compounds represented by the general formula (1) and the general formula (1a) include all geometric isomers and mixtures containing them in an arbitrary ratio.
  • a 1 A 2 , A 3 and A 4 are each a carbon atom, a nitrogen atom or an oxidized nitrogen atom, and A 2 , A 3 and A 4 are all carbon atoms, More preferably, A 2 , A 3 and A 4 are all carbon atoms.
  • [0072] is preferably a hydrogen atom, a C1-C4 alkyl group, or a acetyl group, and more preferably a hydrogen atom, a methyl group, or an ethyl group.
  • R 2 is preferably a hydrogen atom, a C 1 -C 4 alkyl group, or a acetyl group, and more preferably a hydrogen atom, a methyl group, or an ethyl group.
  • both G 2 are preferably oxygen atoms.
  • X is preferably a hydrogen atom or a halogen atom, more preferably , Hydrogen atom, fluorine atom.
  • n is preferably 0, 1 or 2, more preferably 0 if ⁇ is 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.
  • x 2 is preferably a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom.
  • x 3 and x 4 are preferably hydrogen atoms.
  • a phenyl group Preferably, a phenyl group,
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, amino group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyano group
  • Halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, 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, C 1—C 3 alkylsulfinyl group, C 1—C 3 haloalkylsulfinyl group, C 1_C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, amino group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyano
  • Q 2 is preferably a substituted phenyl group or a substituted pyridyl group represented by the general formula (2) or the general formula (3).
  • Y is preferably an optionally substituted C 1 -C 4 alkoxy group, C 1 -C 4 haloalkoxy group, C 1 -C 3 haloalkylthio group, A C 1 -C 3 haloalkylsulfinyl group or a C 1 -C 3 haloalkylsulfonyl group, and more preferably a trifluoromethylthio group, a pentafluoroethylthio group, a heptafluoro_ ⁇ _propylthio group, a heptafluoro mouthpiece i —propylthio group, trifluoromethylsulfinyl group, penta Fluoroethylsulfinyl group, heptafluoro-n-propylsulfinyl group, heptafluoro_ i —propylsulfinyl group, trifluor
  • Y 6 and ⁇ 9 are preferably each independently a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, or an ⁇ -propyl group.
  • Y 3 is preferably a pentafluoroethyl group, a heptafluoro_ ⁇ -propyl pill group, a heptafluoro mouth i-propyl group, a nonafluoro-n_butyl group, a nonafluoro-2-butyl group, a nonafluoro-i_butyl group, trifluoromethylthio Group, pentafluoroethylthio group, heptafluoro_n-propylthio group, heptafluor mouthpiece i-propylthio group, nonafluoro-n-butylthio group, nonafluoro-2-ptylthio group, trifluoromethylsulfinyl group, pentafluro Oloethylsulfinyl group, heptafluoro_n-pylpyrusulfinyl group, heptafluoro peptidyl
  • Y 8 is preferably a pentafluoroethyl group, a heptafluoro_ ⁇ -propyl group, a heptafluor mouth i-propyl group, a nonafluoro-n_butyl group, a nonafluoro-2-butyl group, a nonafluoro-i_butyl group, a trifluoromethylthio group , Pentafluoroethylthio group, heptafluoro_n_propylthio group, heptafluor mouthpiece i —propylthio group, nonafluoro-n-butylthio group, nonafluoro-2-butylthio group, trifluoromethylsulfinyl group, pentafluoro group Loetylsulfinyl group, heptafluoro_n-propylsulfinyl group, heptafluor mouthpiece i-
  • L is preferably a chlorine atom, a bromine atom, or a hydroxy group.
  • Y ia is preferably a trifluoromethylthio group, a pentafluoroethylthio group, a heptafluorine n-propylthio group, a heptafluorine i-propylthio group, a trifluoromethylsulfinyl group, a pentafluoro Loetyl sulfinyl group, heptafluoro _ n-propylsulfinyl group, heptafluoro mouth — i — propylsulfinyl group, trifluoromethylsulfonyl group, pentafluoroethylsulfonyl group, heptafluoro n-propyl sulfonyl group, heptafluoro mouth — i —Propylsulfonyl group, methoxy group, ethoxy group, trifluo
  • Y 2 a preferably as Y 4 a, a hydrogen atom, a halogen atom state, and are a methyl group, more preferably a hydrogen atom.
  • Y 5 a a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, Echiru group, n- propyl group, i - propyl group, n _ butyl group, 2 - heptyl group, Torifuruo L-methyl group, methylthio group, methylsulfinyl group, methylsulfonyl group, trifluoromethylthio group, pentafluoroethylthio group, heptafluor mouthpiece i-propylthio group, trifluoromethylsulfinyl group, pentafluoroe Tylsulfinyl group, heptafluoro
  • R a and R b are each a fluorine atom, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoro_n_propyl group, and more preferably a fluorine atom, A trifluoromethyl group and a pentafluoroethyl group.
  • Nylsulfonyloxy group and p_toluenesulfonyloxy group more preferably a hydroxyl group, a chlorine atom, and a bromine atom.
  • Y 3 , Y 4 , and ⁇ 5 are ⁇ 2 , ⁇ 3 , ⁇ 4 ,
  • a compound represented by the general formula (2 1) is produced by reacting the compound represented by the general formula (19) with the compound represented by the general formula (20) in an appropriate solvent or without a solvent. can do. In this step, an appropriate base can be used.
  • the solvent may be any solvent as long as it does not significantly inhibit the progress of this reaction.
  • examples thereof include water, aromatic hydrocarbons such as benzene, toluene, and xylene, dichloromethane, chloroform, carbon tetrachloride, and the like.
  • 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 Indicates ketones such as ruketone and cyclohexanone, amides such as dimethylformamide, dimethylacetamide, nitriles such as acetonitrile, 1,3-dimethyl-2-imidazolidinone, sulfolane, dimethylsulfoxide, etc. Can dissolve these It can be used as a mixture alone or two or more.
  • 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 metal alcohols such as sodium methoxide and sodium ethoxide It can show the first class.
  • These bases may be appropriately selected and used within the range of 0.01 to 50-fold molar equivalents relative to the compound represented by the general formula (19).
  • the reaction temperature is from _20 ° C to the reflux temperature of the solvent used, and the reaction time is from a few minutes What is necessary is just to select suitably in the range of 96 hours, respectively.
  • m_nitro aromatic force ruponic acid halide is halogenated with the corresponding aromatic carboxylic acid. It can be easily produced by reacting the agent.
  • the halogenating agent include halogenating agents such as thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride, phosphorus trichloride, and phosgene.
  • 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.
  • a catalyst include palladium catalysts such as palladium-carbon, nickel catalysts such as Raney-nickel, platinum catalysts, cobalt catalysts, ruthenium catalysts, rhodium catalysts, etc.
  • Solvents include water, methanol And alcohols such as ethanol, aromatic hydrocarbons 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 10 MPa
  • the reaction temperature is _20 ° 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. ) Can be efficiently produced.
  • 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 such as jetyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxetane
  • Examples of the base include organic bases such as triethylamine, tri-n-ptylamine, pyridine, and 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 50 times molar equivalent 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 to be used, and the reaction time may be appropriately selected within the range of several minutes to 96 hours. It can also be produced by a method using the condensing agent described in 1_ (i) or a mixed acid anhydride method.
  • dimethyl sulfate dimethyl sulfate
  • dimethyl sulfate dimethyl sulfate
  • an alkylating agent such as an acid or jetyl sulfate
  • the solvent and the base described in the above (1) (i) are appropriately selected, or the carboxylic acid having an amino group represented by the general formula (27) and the general formula (23) By reacting with the compound represented, the carboxylic acid having an acylamino group represented by the general formula (28) can be produced.
  • the reaction time and reaction temperature can be appropriately selected from the conditions described in 1_ (i) above.
  • a compound represented by the general formula (29) can be produced by a halogenation reaction.
  • a 2 , A 3 , A 4 , X, n, G 2 , R 2 are AA 2 , A 3 , A 4 , X in [1]. , N, G 2 and R 2 .
  • the compound represented by the general formula (48) is reacted with an appropriate reagent in an appropriate solvent or without a solvent using an appropriate base, and the compound represented by the general formula (49) is obtained. Can be manufactured.
  • the solvent is not particularly limited as long as it 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 Formamide, dimethyl Amides such as acetoamide, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methylisobutylketone, cyclohexanone and methylethylketone, esters such as ethyl acetate and butyl acetate, methanol, ethanol And alcohols such as 1,3-dimethyl-1,2-imidazolidinone, sulfolane, dimethyl sulfoxide, water and the like. These solvents may 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, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium hydrogen carbonate, potassium carbonate Carbonates such as sodium phosphate, phosphates such as potassium monohydrogen phosphate and trisodium phosphate, alkali metal hydrides such as sodium hydride, alkali metal alkoxides such as sodium methoxide and sodium metoxide , Organic lithiums such as n-butyllithium, and Grignard reagents such as ethylmagnesium bromide.
  • organic bases such as trytylamine, triptylamin, pyridine and 4-dimethylaminopyridine
  • alkali metal hydroxides such as sodium hydroxide and potassium hydroxide
  • sodium hydrogen carbonate potassium carbonate
  • potassium carbonate Carbonates such as sodium phosphate
  • phosphates such as potassium monohydrogen phosphate
  • Examples of the reactants include halogenated alkyls such as methyl iodide, acetyl bromide, trifluoromethyl iodide, 2,2,2_trifluoroethyl iodide, and halogenated 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 or used as a solvent in the range of 1 to 5 molar equivalents relative to the compound represented by the general formula (48).
  • the reaction temperature may be appropriately selected from 180 ° C. to the reflux temperature of the solvent to be used, and the reaction time may be selected within the range of several minutes to 96 hours.
  • ⁇ 2 , ⁇ 3 , ⁇ 4 , X, ⁇ , G 2 , R 2 are A, A 2 , A 3 , A 4 in the above [1]. , X, n, G 2 and R 2 .
  • 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 catalyst for example, palladium catalysts such as palladium, bon-nickel, nickel catalysts such as Raney nickel, cobalt catalysts, platinum catalysts, ruthenium catalysts, rhodium catalysts, etc. can be shown.
  • aldehydes include aldehydes such as formaldehyde, acetoaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoracetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, and promoacetoaldehyde. Can show.
  • ketones examples include ketones such as acetone, perfluoroacetone, and methyl ethyl ketone.
  • reaction pressure may be appropriately selected within the range of 0.1 M Pa to 1 O M Pa.
  • 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 compound represented by the general formula (50) can be obtained. Can be produced.
  • 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 such as dichloromethane, black mouth form, carbon tetrachloride, halogenated hydrocarbons such as 1,2-dichloroethane, ethers such as jetyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxetane, Amides such as dimethylformamide, dimethylacetamide, nitriles such as acetonitrile, propionitrile, ketones such as acetone, methylisobutylketone, cyclohexanone, methylethylketone, ethyl acetate, butyl acetate, etc.
  • the reducing agent include polohydrides such as sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride and the like.
  • aldehydes examples include aldehydes such as formaldehyde, acetoaldehyde, propionaldehyde, trifluoroacetaldehyde, difluoroacetaldehyde, fluoracetaldehyde, chloroacetaldehyde, dichloroacetaldehyde, trichloroacetaldehyde, and promoacetaldehyde. Can be shown.
  • ketones examples 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 within the range of several minutes to 96 hours.
  • R in the general formula (50) is a methyl group. Can be produced.
  • 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 _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.
  • additives include inorganic acids such as sulfuric acid, organic acids such as formic acid, polohydrides such as sodium polohydride, sodium cyanoporohydride, boronic acid, lithium aluminum hydride, etc.
  • inorganic acids such as sulfuric acid
  • organic acids such as formic acid
  • polohydrides such as sodium polohydride, sodium cyanoporohydride, boronic acid, lithium aluminum hydride, etc.
  • the reaction temperature is from 20 ° C to the reflux temperature of the solvent used.
  • the reaction time is from a few minutes.
  • R 2 , ⁇ 2 , ⁇ 3 , ⁇ 4 , ⁇ 5 are R 2 , ⁇ 2 , ⁇ 3 , ⁇ 4 , ⁇ in [1] above. 5 is synonymous with, m represents 1 or 2
  • R f represents a C 1 -C 3 haloalkyl group.
  • a compound represented by the general formula (32) can be produced from a compound represented by the general formula (3 1).
  • the oxidizing agent examples include organic peracids such as m_cloperbenzoic acid, sodium metaperiodate, hydrogen peroxide, ozone, selenium dioxide, chromic acid, dinitrogen tetraoxide, and acyl chloride. Iodine, bromine, N-promosuccinic acid imide, sodium benzyl chloride, t-butyl hypochlorite, etc. can be shown.
  • the oxidizing agent is appropriately selected within the range of 1 to 5 times molar equivalent to the compound represented by the general formula (3 1). You can choose.
  • 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. These solvents may be used alone or in combination of two kinds. They can be used in combination.
  • the reaction temperature is one
  • 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.
  • n- is normal
  • Me is methyl
  • E t is ethyl
  • n _ P r is normal propyl
  • i _P r Is an isopropyl 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 '' is a hydrogen atom
  • ⁇ 0 '' is an oxygen atom
  • ⁇ S '' is a sulfur atom
  • ⁇ C '' is a carbon atom
  • ⁇ N '' is a nitrogen atom
  • ⁇ F '' is a fluorine atom
  • CI is a chlorine atom
  • B r is a bromine atom
  • I is an iodine atom
  • CF 3 represents a trifluoromethyl group
  • C 2 F 5 represents a pentafluoroethyl group
  • n _C 3 F 7 represents a heptafluoro_n-propyl group
  • i _C 3 F 7 Is a heptafluoro_ i —propyl group
  • 2_C 4 F 9 is a nonafluoro-2-ptyl group
  • SCF 3 is a trifluoromethylthio group
  • SC 2 F 5 is a pentafluoroethylthio group
  • S_n_C 3 F 7 is heptafluoro_n —propylthio group
  • S (O) CF 3 is trifluoromethylsulfinyl group
  • S (O) C 2 F 5 is pentafluoroethylsulfinyl group ⁇ S (O) _n_
  • Loetylsulfonyl group “S0 2 _n_C 3 F 7” is heptafluor _ N-propylsulfonyl group, “OM e” is a methoxy group, “OE t” is an ethoxy group, “OC F 3 ” is a trifluoromethoxy group, and “OCH 2 CF” is 2, 2, 2 —Trifluoroethoxy group, “OCH (CF 3 ) 2 ” represents 1, 1, 1, 3, 3, 3_hexafluoro-2-propyloxy group, and “A c” represents acetyl group. is there.

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne une composition de lutte contre les organismes nuisibles caractérisée par le fait qu'elle contient un composé représenté par la formule générale (1) ci-après et un insecticide connu publiquement, un acaricide connu publiquement ou un bactéricide connu publiquement en tant qu'ingrédients actifs. Dans la formule (1) ci-après, A1, A2, A3 et A4 représentent respectivement un atome de carbone, un atome d'azote et un atome d'azote oxydé ; R1 et R2 représentent indépendamment un atome d'hydrogène, un groupe alkyle en C1-C4 ou un groupe alkylcarbonyle en C1-C4 ; G1 et G2 représentent indépendamment un atome d'oxygène ou un atome de soufre ; et les X peuvent être identiques ou différents et représentent un atome d'hydrogène, un atome d'halogène ou un groupe trifluorométhyle. (1)
PCT/JP2007/001347 2006-12-19 2007-12-05 Composition de lutte contre les organismes nuisibles WO2008075453A1 (fr)

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JP2006340922A JP2010047479A (ja) 2006-12-19 2006-12-19 有害生物防除組成物

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WO2012015014A1 (fr) * 2010-07-29 2012-02-02 石原産業株式会社 Agent de perturbation de l'accouplement des insectes nuisibles suceurs de sève
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CN103999656A (zh) * 2014-05-05 2014-08-27 郎溪县十字镇林华粮食种植家庭农场 一种可有效增产小麦种植技术
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CN116369094A (zh) * 2023-06-06 2023-07-04 吉林省艺道科技有限公司 一种可自控通腰风防滴水降湿温室大棚

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CN108164502B (zh) * 2018-03-06 2021-04-13 苏州华一新能源科技有限公司 1,3-丙烷磺酸内酯的制备方法

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JPWO2010013567A1 (ja) * 2008-08-01 2012-01-12 三井化学アグロ株式会社 アミド誘導体、該アミド誘導体を含有する有害生物防除剤および有害生物の防除方法
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