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WO2014148451A1 - Composé hétérocyclique condensé ou son sel, pesticide pour un usage agricole et horticole contenant ledit composé et son procédé d'utilisation - Google Patents

Composé hétérocyclique condensé ou son sel, pesticide pour un usage agricole et horticole contenant ledit composé et son procédé d'utilisation Download PDF

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Publication number
WO2014148451A1
WO2014148451A1 PCT/JP2014/057214 JP2014057214W WO2014148451A1 WO 2014148451 A1 WO2014148451 A1 WO 2014148451A1 JP 2014057214 W JP2014057214 W JP 2014057214W WO 2014148451 A1 WO2014148451 A1 WO 2014148451A1
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group
halo
alkyl group
alkoxy
alkyl
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PCT/JP2014/057214
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English (en)
Japanese (ja)
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樹 米村
浩介 深津
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日本農薬株式会社
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Publication of WO2014148451A1 publication Critical patent/WO2014148451A1/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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Definitions

  • the present invention relates to an agricultural and horticultural insecticide containing a certain type of condensed heterocyclic compound or a salt thereof as an active ingredient, and a method for using the same.
  • the condensed heterocyclic compound represented by the general formula (I) or a salt thereof has an excellent control effect against agricultural and horticultural pests.
  • the present invention has been reached.
  • R 1 is (A1) a (C 1 -C 6 ) alkyl group; (A2) a (C 3 -C 6 ) cycloalkyl group; (A3) (C 2 -C 6 ) alkenyl group; (A4) (C 2 -C 6 ) alkynyl group; (A5) a halo (C 1 -C 6 ) alkyl group; (A6) a halo (C 3 -C 6 ) cycloalkyl group; (A7) a halo (C 2 -C 6 ) alkenyl group; (A8) a halo (C 2 -C 6 ) alkynyl group; (A9) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (A10) a halo (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (A11) a (C 3 -
  • R 2 is (B1) a halogen atom; (B2) a cyano group; (B3) a nitro group; (B4) a (C 1 -C 6 ) alkyl group; (B5) (C 3 -C 6 ) cycloalkyl group; (B6) (C 2 -C 6 ) alkenyl group; (B7) a (C 2 -C 6 ) alkynyl group; (B8) a halo (C 1 -C 6 ) alkyl group; (B9) a halo (C 3 -C 6 ) cycloalkyl group; (B10) a halo (C 2 -C 6 ) alkenyl group; (B11) a halo (C 2 -C 6 ) alkynyl group; (B12) a (C 1 -C 6 ) alkylthio group; (B13) a (C 1 -C 6 ) alkylsulfinyl group;
  • R 3 is (C1) a hydrogen atom; (C2) a halogen atom; (C3) a cyano group; (C4) a nitro group; (C5) a (C 1 -C 6 ) alkyl group; (C6) (C 1 -C 6 ) alkoxy group; (C7) (C 2 -C 6 ) alkenyloxy group; (C8) (C 2 -C 6 ) alkynyloxy group; (C9) a halo (C 1 -C 6 ) alkyl group; (C10) a halo (C 1 -C 6 ) alkoxy group; (C11) a halo (C 2 -C 6 ) alkenyloxy group; (C12) a halo (C 2 -C 6 ) alkynyloxy group; (C13) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (C14) a halo (
  • R 4 is (D1) a hydrogen atom; (D2) a halogen atom; (D3) a cyano group; (D4) a nitro group; (D5) a (C 1 -C 6 ) alkyl group; (D6) a (C 1 -C 6 ) alkoxy group; (D7) a (C 2 -C 6 ) alkenyloxy group; (D8) (C 2 -C 6 ) alkynyloxy group; (D9) a halo (C 1 -C 6 ) alkyl group; (D10) a halo (C 1 -C 6 ) alkoxy group; (D11) a halo (C 2 -C 6 ) alkenyloxy group; (D12) a halo (C 2 -C 6 ) alkynyloxy group; (D13) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (D14) a
  • R 5 is (E1) a hydrogen atom; (E2) formyl group; (E3) a (C 1 -C 6 ) alkyl group; (E4) (C 3 -C 6 ) cycloalkyl group; (E5) a halo (C 1 -C 6 ) alkyl group; (E6) a halo (C 3 -C 6 ) cycloalkyl group; (E7) a (C 1 -C 6 ) alkylsulfonyl group; (E8) a halo (C 1 -C 6 ) alkylsulfonyl group; (E9) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (E10) a halo (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (E11) a (C 1 -C 6 ) alkoxyhalo (C 1 -C 6 ) al
  • R 6 is (F1) a hydrogen atom; (F2) formyl group; (F3) a (C 1 -C 6 ) alkyl group; (F4) (C 3 -C 6 ) cycloalkyl group; (F5) a halo (C 1 -C 6 ) alkyl group; (F6) a halo (C 3 -C 6 ) cycloalkyl group; (F7) a (C 1 -C 6 ) alkylsulfonyl group; (F8) a halo (C 1 -C 6 ) alkylsulfonyl group; (F9) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (F10) a halo (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (F11) represents a (C 1 -C 6 ) alkoxyhalo (C 1 -C 6 )
  • a 1 , A 2 , and A 3 may be the same or different and each represents a nitrogen atom or a C—R 7 group (where R 7 is (G1) a hydrogen atom; (G2) a halogen atom; (G3) a cyano group; (G4) a nitro group; (G5) formyl group; (G6) a (C 1 -C 6 ) alkyl group; (G7) (C 1 -C 6 ) alkoxy group; (G8) (C 2 -C 6 ) alkenyloxy group; (G9) (C 2 -C 6 ) alkynyloxy group; (G10) (C 3 -C 6 ) cycloalkoxy group; (G11) a halo (C 1 -C 6 ) alkyl group; (G12) a halo (C 1 -C 6 ) alkoxy group; (G13) a halo (C 2 -C 6 ) alkenyloxy group; (G14
  • [2] m is synonymous with the above [1], R 1 is (a1) (C 1 -C 6 ) alkyl; R 2 is a (b8) halo (C 1 -C 6 ) alkyl group, R 3 is (c1) a hydrogen atom; or (c2) a halogen atom, R 4 is (d1) a hydrogen atom, R 5 is (e5) a halo (C 1 -C 6 ) alkyl group; or (e13) a halo (C 1 -C 6 ) alkylthio group, R 6 is a (f3) (C 1 -C 6 ) alkyl group, A 1 and A 2 are C—R 7 groups (where R 7 is a (g1) hydrogen atom), and A 3 is a C—R 7 group (where R 7 is a (g1) hydrogen atom) or nitrogen
  • [3] m is synonymous with [1], R 1 is (a1) (C 1 -C 6 ) alkyl; R 2 is a (b8) halo (C 1 -C 6 ) alkyl group, R 3 is (c1) a hydrogen atom, R 4 is (d1) a hydrogen atom, R 5 is (e5) a halo (C 1 -C 6 ) alkyl group, R 6 is a (f3) (C 1 -C 6 ) alkyl group, A 1 and A 2 are C—R 7 groups (where R 7 is a (g1) hydrogen atom), and A 3 is a C—R 7 group (where R 7 is a (g1) hydrogen atom).
  • R 1 is (a1) (C 1 -C 6 ) alkyl
  • R 2 is a (b8) halo (C 1 -C 6 ) alkyl group
  • R 3 is (c1) a hydrogen atom
  • R 4 is (d1) a hydrogen atom
  • R 5 is (
  • [4] Use of the fused heterocyclic compound or salt thereof according to any one of [1] to [3] as an agricultural and horticultural insecticide
  • [5] A method for using an agricultural and horticultural insecticide characterized by treating an active ingredient of the agricultural and horticultural insecticide according to [4] to a plant or soil
  • [6] A method for controlling agricultural and horticultural pests, which comprises treating a plant or soil with an effective amount of the agricultural and horticultural insecticide according to [4],
  • [7] An ectoparasite control agent comprising the condensed heterocyclic compound or a salt thereof according to any one of [1] to [3] as an active ingredient
  • [8] A method for controlling ectoparasites, comprising treating the ectoparasite with an effective amount of the ectoparasite control agent according to [7], [9]
  • R 1 is (A1) a (C 1 -C 6 ) alkyl group; (A2) a (C 3 -C 6 ) cycloalkyl group; (A3) (C 2 -C 6 ) alkenyl group; (A4) (C 2 -C 6 ) alkynyl group; (A5) a halo (C 1 -C 6 ) alkyl group; (A6) a halo (C 3 -C 6 ) cycloalkyl group; (A7) a halo (C 2 -C 6 ) alkenyl group; (A8) a halo (C 2 -C 6 ) alkynyl group; (A9) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (A10) a halo (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (A11) a (C 3 -
  • R 2 is (B1) a halogen atom; (B2) a cyano group; (B3) a nitro group; (B4) a (C 1 -C 6 ) alkyl group; (B5) (C 3 -C 6 ) cycloalkyl group; (B6) (C 2 -C 6 ) alkenyl group; (B7) a (C 2 -C 6 ) alkynyl group; (B8) a halo (C 1 -C 6 ) alkyl group; (B9) a halo (C 3 -C 6 ) cycloalkyl group; (B10) a halo (C 2 -C 6 ) alkenyl group; (B11) a halo (C 2 -C 6 ) alkynyl group; (B12) a (C 1 -C 6 ) alkylthio group; (B13) a (C 1 -C 6 ) alkylsulfinyl group;
  • R 3 is (C1) a hydrogen atom; (C2) a halogen atom; (C3) a cyano group; (C4) a nitro group; (C5) a (C 1 -C 6 ) alkyl group; (C6) (C 1 -C 6 ) alkoxy group; (C7) (C 2 -C 6 ) alkenyloxy group; (C8) (C 2 -C 6 ) alkynyloxy group; (C9) a halo (C 1 -C 6 ) alkyl group; (C10) a halo (C 1 -C 6 ) alkoxy group; (C11) a halo (C 2 -C 6 ) alkenyloxy group; (C12) a halo (C 2 -C 6 ) alkynyloxy group; (C13) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (C14) a halo (
  • R 4 is (D1) a hydrogen atom; (D2) a halogen atom; (D3) a cyano group; (D4) a nitro group; (D5) a (C 1 -C 6 ) alkyl group; (D6) a (C 1 -C 6 ) alkoxy group; (D7) a (C 2 -C 6 ) alkenyloxy group; (D8) (C 2 -C 6 ) alkynyloxy group; (D9) a halo (C 1 -C 6 ) alkyl group; (D10) a halo (C 1 -C 6 ) alkoxy group; (D11) a halo (C 2 -C 6 ) alkenyloxy group; (D12) a halo (C 2 -C 6 ) alkynyloxy group; (D13) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (D14) a
  • R 5 is (E1) a hydrogen atom; (E2) formyl group; (E3) a (C 1 -C 6 ) alkyl group; (E4) (C 3 -C 6 ) cycloalkyl group; (E5) a halo (C 1 -C 6 ) alkyl group; (E6) a halo (C 3 -C 6 ) cycloalkyl group; (E7) a (C 1 -C 6 ) alkylsulfonyl group; (E8) a halo (C 1 -C 6 ) alkylsulfonyl group; (E9) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (E10) a halo (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (E11) represents a (C 1 -C 6 ) alkoxyhalo (C 1 -C 6 )
  • R 6 is (F1) a hydrogen atom; (F2) formyl group; (F3) a (C 1 -C 6 ) alkyl group; (F4) (C 3 -C 6 ) cycloalkyl group; (F5) a halo (C 1 -C 6 ) alkyl group; (F6) a halo (C 3 -C 6 ) cycloalkyl group; (F7) a (C 1 -C 6 ) alkylsulfonyl group; (F8) a halo (C 1 -C 6 ) alkylsulfonyl group; (F9) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (F10) a halo (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (F11) represents a (C 1 -C 6 ) alkoxyhalo (C 1 -C 6 )
  • a 1 , A 2 , and A 3 may be the same or different and each represents a nitrogen atom or a C—R 7 group (where R 7 is (G1) a hydrogen atom; (G2) a halogen atom; (G3) a cyano group; (G4) a nitro group; (G5) formyl group; (G6) a (C 1 -C 6 ) alkyl group; (G7) (C 1 -C 6 ) alkoxy group; (G8) (C 2 -C 6 ) alkenyloxy group; (G9) (C 2 -C 6 ) alkynyloxy group; (G10) (C 3 -C 6 ) cycloalkoxy group; (G11) a halo (C 1 -C 6 ) alkyl group; (G12) a halo (C 1 -C 6 ) alkoxy group; (G13) a halo (C 2 -C 6 ) alkenyloxy group; (G14
  • R 1 is (a1) (C 1 -C 6 ) alkyl
  • R 2 is a (b8) halo (C 1 -C 6 ) alkyl group
  • R 3 is (c1) a hydrogen atom; or (c2) a halogen atom
  • R 4 is (d1) a hydrogen atom
  • R 5 is (e5) a halo (C 1 -C 6 ) alkyl group
  • R 6 is a (f3) (C 1 -C 6 ) alkyl group
  • a 1 and A 2 are a C—R 7 group (where R 7 is a (g1) hydrogen atom) and A 3 is a C—R 7 group (where R 7 is a (g1) hydrogen atom) or
  • [12] m is synonymous with [10], R 1 is (a1) (C 1 -C 6 ) alkyl; R 2 is a (b8) halo (C 1 -C 6 ) alkyl group, R 3 is (c1) a hydrogen atom, R 4 is (d1) a hydrogen atom, R 5 is (e5) a halo (C 1 -C 6 ) alkyl group, R 6 is a (f3) (C 1 -C 6 ) alkyl group, A 1 and A 2 are a C—R 7 group (where R 7 is a (g1) hydrogen atom) and A 3 is a C—R 7 group (where R 7 is a (g1) hydrogen atom) or The condensed heterocyclic compound and a salt thereof according to [10], which is a nitrogen atom;
  • [13] Use of the fused heterocyclic compound or salt thereof according to any one of [10] to [12] as an agricultural and horticultural insecticide
  • [14] A method for using an agricultural and horticultural insecticide characterized by treating an active ingredient of the agricultural and horticultural insecticide according to [13] to a plant or soil
  • a method for controlling agricultural and horticultural pests which comprises treating an effective amount of the agricultural and horticultural insecticide according to [13] with plants or soil
  • An ectoparasite control agent comprising the condensed heterocyclic compound or a salt thereof according to any one of [10] to [12] as an active ingredient
  • [17] A method for controlling ectoparasites, which comprises treating an ectoparasite with an effective amount of the ectoparasite control agent according to [16].
  • [18] An insecticide containing, as an active ingredient, a pyrrolopyridazine fused heterocyclic compound exemplified by a compound of the general formula (1) or a salt thereof, [19] The insecticide according to [18], wherein the pyrrolopyridazine fused heterocycle is a pyrrolo [2,3-C] pyridazine fused heterocycle, [20] An agricultural and horticultural insecticide containing the fused heterocyclic compound or salt thereof according to any one of [1] to [3] or [10] to [12], [21] A method for using an agricultural and horticultural insecticide characterized by treating a plant or soil with an active ingredient of the agricultural and horticultural insecticide according to [20], and the agricultural and horticultural science according to [22] and [20] A method for controlling agricultural and horticultural pests, characterized by treating an effective amount of an insecticide for plants or soil, About.
  • the fused heterocyclic compound of the present invention or a salt thereof not only has an excellent effect as an agricultural and horticultural insecticide, but also against harmful insects parasitic on the outside or inside of pets such as dogs and cats, or domestic animals such as cattle and sheep. Even has an effect.
  • halo means “halogen atom”, and represents a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
  • (C 1 -C 6 ) alkyl group means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group Tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group, A linear or branched alkyl group having 1 to 6 carbon atoms such as 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group, etc.
  • (C 2 -C 6 ) alkenyl group means, for example, vinyl group, allyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2- A linear or branched alkenyl group having 2 to 6 carbon atoms such as propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group, etc.
  • (C 2 -C 6 ) alkynyl means, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 3-methyl-1-propynyl
  • Straight chain or branched carbon atoms such as 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group, 3,3-dimethyl-1-butynyl group, etc.
  • (C 3 -C 6 ) cycloalkyl refers to a cyclic alkyl group having 3 to 6 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • Examples of the “(C 1 -C 6 ) alkoxy group” include a methoxy group, an ethoxy group, a normal propoxy group, an isopropoxy group, a normal butoxy group, a secondary butoxy group, a tertiary butoxy group, a normal pentyloxy group, and isopentyl.
  • a straight-chain or branched alkoxy group having 1 to 6 carbon atoms such as 2-trimethylpropyloxy group
  • Examples of the “(C 2 -C 6 ) alkenyloxy group” include linear or branched alkenyloxy groups having 2 to 6 carbon atoms such as propenyloxy group, butenyloxy group, pentenyloxy group, hexenyloxy group and the like.
  • Examples of the “(C 2 -C 6 ) alkynyloxy group” include linear or branched alkynyloxy having 2 to 6 carbon atoms such as propynyloxy group, butynyloxy group, pentynyloxy group, hexynyloxy group and the like. Indicates a group.
  • Examples of the “(C 1 -C 6 ) alkylthio group” include a methylthio group, an ethylthio group, a normal propylthio group, an isopropylthio group, a normal butylthio group, a secondary butylthio group, a tertiary butylthio group, and a normal pentylthio group.
  • Examples of the “(C 1 -C 6 ) alkylsulfinyl group” include, for example, methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, Normal pentylsulfinyl group, isopen
  • Examples of the “(C 2 -C 6 ) alkenylthio group” include straight chain or branched chain alkenylthio having 2 to 6 carbon atoms such as propenylthio group, butenylthio group, pentenylthio group, hexenylthio group and the like.
  • Examples of the “(C 2 -C 6 ) alkynylthio group” include linear or branched alkynylthio groups having 2 to 6 carbon atoms such as propynylthio group, butynylthio group, pentynylthio group, hexynylthio group and the like. Show.
  • Examples of the “(C 2 -C 6 ) alkenylsulfinyl group” include straight chain or branched chain carbon atoms having 2 to 6 carbon atoms such as propenylsulfinyl group, butenylsulfinyl group, pentenylsulfinyl group, hexenylsulfinyl group and the like.
  • Examples of the “(C 2 -C 6 ) alkynylsulfinyl group” include straight chain or branched chain carbon atoms of 2 to 6 such as propynylsulfinyl group, butynylsulfinyl group, pentynylsulfinyl group, hexynylsulfinyl group and the like. Each alkynylsulfinyl group.
  • Examples of the “(C 2 -C 6 ) alkenylsulfonyl group” include straight chain or branched chain carbon atoms having 2 to 6 carbon atoms such as propenylsulfonyl group, butenylsulfonyl group, pentenylsulfonyl group, hexenylsulfonyl group and the like.
  • Examples of the “(C 2 -C 6 ) alkynylsulfonyl group” include linear or branched carbon atoms of 2 to 6 such as propynylsulfonyl group, butynylsulfonyl group, pentynylsulfonyl group, hexynylsulfonyl group and the like. Each alkynylsulfonyl group.
  • (C 3 -C 6 ) cycloalkoxy group means, for example, a cyclic alkoxy group having 3 to 6 carbon atoms such as cyclopropoxy group, cyclobutoxy group, cyclopentyloxy group, cyclohexyloxy group, etc.
  • “(C 3 -C 6 ) cycloalkylthio group” refers to, for example, a cyclic alkylthio group having 3 to 6 carbon atoms such as cyclopropylthio group, cyclobutylthio group, cyclopentylthio group, cyclohexylthio group and the like.
  • (C 3 -C 6 ) cycloalkylsulfinyl group means, for example, a cyclic alkylsulfinyl group having 3 to 6 carbon atoms such as cyclopropylsulfinyl group, cyclobutylsulfinyl group, cyclopentylsulfinyl group, cyclohexylsulfinyl group and the like.
  • (C 3 -C 6 ) cycloalkylsulfonyl group refers to a cyclic alkylsulfonyl group having 3 to 6 carbon atoms such as cyclopropylsulfonyl group, cyclobutylsulfonyl group, cyclopentylsulfonyl group, cyclohexylsulfonyl group and the like. Show.
  • Examples of the salt of the condensed heterocyclic compound represented by the general formula (I) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate, acetate, fumarate, maleate, and salt.
  • examples include organic acid salts such as acid salts, methanesulfonate, benzenesulfonate, and paratoluenesulfonate, and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium. it can.
  • the condensed heterocyclic compound represented by the general formula (I) and salts thereof of the present invention may have one or more asymmetric centers in the structural formula, and two or more optical isomers and dia Stereomers may exist, and the present invention includes all the optical isomers and a mixture in which they are contained in an arbitrary ratio.
  • the compound represented by the general formula (I) and salts thereof of the present invention may have two geometric isomers derived from a carbon-carbon double bond in the structural formula. Includes all geometric isomers and mixtures containing them in any proportion.
  • a 1 and A 2 are preferably CH, A 3 is preferably CH or a nitrogen atom, and R 1 is (C 1 —C 6 ) alkyl group is preferred, R 2 is preferably a halogen atom, (C 1 -C 6 ) alkyl group, or halo (C 1 -C 6 ) alkyl group, and R 3 and R 4 are preferably hydrogen atoms.
  • R 5 is preferably a halogen atom, a (C 1 -C 6 ) alkyl group, or a halo (C 1 -C 6 ) alkyl group
  • R 6 is preferably a (C 1 -C 6 ) alkyl group
  • m is , 0, 1 or 2 are preferred.
  • R 1 is preferably a (C 1 -C 6 ) alkyl group
  • R 2 is halo (C 1 -C 6 ) alkyl group
  • R 3 is a hydrogen atom or a halogen atom
  • R 4 is a hydrogen atom
  • R 5 is a halo (C 1 -C 6 ) alkyl group or halo (C 1 -C 6 )
  • An alkylthio group R 6 is a (C 1 -C 6 ) alkyl group
  • a 1 and A 2 are CH groups
  • a 3 is a CH group or a nitrogen atom
  • m is 0, 1 or 2 It is.
  • R 1 is a (C 1 -C 6 ) alkyl group
  • R 2 is a halo (C 1 -C 6 ) alkyl group
  • R 3 is a hydrogen atom
  • R 4 is a hydrogen atom
  • R 5 is a halo (C 1 -C 6 ) alkyl group
  • R 6 is a (C 1 -C 6 ) alkyl group
  • a 1 , A 2 and A 3 are CH groups
  • m is 0, 1 or 2.
  • the complex heterocyclic compound or a salt thereof of the present invention can be produced, for example, by the following production method, but the present invention is not limited to these.
  • R 1 , R 2 , R 4 , R 5 , R 6 , A 1 , A 2 , and A 3 are as defined above, m represents 1 or 2, and R represents a methyl group, ethyl An alkyl group such as a group is shown.
  • X represents a bromine atom or an iodine atom.
  • Examples of the palladium catalyst that can be used include palladium (II) acetate, dichlorobis (triphenylphosphine) palladium (II), tetrakis (triphenylphosphine) palladium (0), and dichloroditriphenylphosphinopalladium (0). , Tris (dibenzylideneacetone) dipalladium (0), diphenylphosphinoferrocenedichloropalladium (II) and the like.
  • the amount of the palladium catalyst to be used is generally 0.01 to 0.5 mol with respect to 1 mol of the compound.
  • copper compounds examples include monovalent copper halides such as cuprous fluoride, cuprous chloride, cuprous bromide, cuprous iodide, cupric chloride, bromide. Examples thereof include divalent copper halides such as cupric and cupric iodide.
  • the amount of copper halide to be used is generally 0.1-1 mol per 1 mol of compound (6).
  • a base is further used.
  • the base include sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, cesium carbonate, potassium phosphate and other inorganic bases, or triethylamine, pyridine, Examples include amines such as piperidine.
  • the amount of the base to be used is generally 1 to 10 mol per 1 mol of compound (6).
  • This reaction can be carried out in a solvent.
  • the organic solvent that can be used is not particularly limited as long as it is inert to the reaction.
  • ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran
  • aromatic hydrocarbon solvents such as toluene, benzene and xylene
  • aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvents
  • Amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone
  • Nitrile solvents such as acetonitrile and benzonitrile
  • the reaction temperature should be a temperature sufficient to complete the coupling reaction, and is usually within the range of room temperature to the boiling point of the solvent used.
  • the reaction time is usually several minutes to several tens of hours.
  • the reaction is preferably carried out in an inert gas atmosphere. After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • Step b Compound (4) is obtained by desilylating compound (5) according to the method described in Greene's Protecting Group in Organic Synthesis (3rd ed .; Wiley: New York, 1999). It can be produced by a chemical reaction. A method of mixing with tetrabutylammonium fluoride in a suitable solvent (for example, THF, methylene chloride, etc.) can be mentioned. The reaction proceeds easily from 0 ° C. to room temperature.
  • a suitable solvent for example, THF, methylene chloride, etc.
  • Step c Production method of [Step c]
  • Compound (2) can be obtained by Sonogashira reaction using Compound (3), Compound (4), which is an acetylene derivative, a palladium catalyst, and a copper compound, [Step a] It can be manufactured by the same method as the manufacturing method.
  • Step d Compound (I-2) can be produced by reacting compound (2) with an appropriate base in an inert solvent.
  • the inert solvent that can be used is not particularly limited as long as it is inert to the reaction.
  • ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran
  • aromatic hydrocarbon solvents such as toluene, benzene and xylene
  • aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvents
  • Amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone
  • Nitrile solvents such as acetonitrile and benzonitrile
  • bases examples include inorganic bases such as sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, cesium carbonate, and potassium phosphate.
  • examples thereof include alkoxides such as potassium tert-butoxide, sodium methoxide and sodium ethoxide, alkali metal hydrides such as sodium hydride and potassium hydride, and amines such as triethylamine, pyridine and piperidine.
  • the amount of the base to be used is generally 1 to 10 mol per 1 mol of compound (2).
  • the reaction temperature is usually within the range of room temperature to the boiling point of the solvent used.
  • the reaction time is usually several minutes to several tens of hours.
  • the reaction is preferably carried out in an inert gas atmosphere.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. [Step b], [Step c], and [Step d] can also be performed continuously without a purification step.
  • a condensed heterocyclic compound represented by the general formula (I-1) is obtained by reacting the condensed heterocyclic compound represented by the general formula (I-2) with an oxidizing agent in an inert solvent.
  • an oxidizing agent used in this reaction include peroxides such as hydrogen peroxide solution, perbenzoic acid, and m-chloroperbenzoic acid.
  • These oxidizing agents can be appropriately selected in the range of 0.8-fold to 5-fold moles with respect to the condensed heterocyclic compounds represented by the general formula (I-2), preferably 1-fold mole to A range of 2 moles is preferred.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction.
  • examples thereof include linear or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic carbonization such as benzene, toluene, and xylene.
  • Halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; Nitriles such as acetonitrile; Esters such as ethyl acetate; Formic acid and acetic acid Organic solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-imidazolinone, water and the like, and these inert solvents may be used alone or A mixture of more than one species can be used.
  • the reaction temperature in this reaction may be appropriately selected within the range of ⁇ 10 ° C. to the reflux temperature of the inert solvent used.
  • the reaction time varies depending on the reaction scale, reaction temperature, and the like, and is not constant but may be appropriately selected within the range of several minutes to 48 hours.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • a substituent other than hydrogen represented by R 3 in the compound (I) is introduced by a known method or a method known per se. May be.
  • the intermediate of the present invention can be produced, for example, by the following method.
  • Intermediate production method
  • the compound represented by the general formula (3-1) is prepared by combining a compound represented by the general formula (3-2) and an amino compound represented by the general formula (8) in an inert solvent. Can be synthesized from The amino compound (8) can be appropriately selected in the range of 1-fold mol to 5-fold mol with respect to the compound (3-2).
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • halogens such as methylene chloride, chloroform and carbon tetrachloride.
  • Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, linear or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, dimethylformamide, dimethyl Amides such as acetamide, ketones such as acetone and methyl ethyl ketone; and inert solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone can be exemplified, and these inert solvents can be used alone or as 2 Can be used by mixing more than one species
  • a base may be used as necessary.
  • the base include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; sodium acetate, potassium acetate Acetates such as potassium t-butoxide, sodium methoxide, sodium ethoxide, and other alkali metal alkoxides, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene, etc.
  • Secondary amines; nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine, etc. can be mentioned, and the amount used is usually 1 to 10 mol per mol of the compound represented by formula (3-2). Used in the range of
  • the reaction temperature in this reaction may be appropriately selected within the range of ⁇ 10 ° C. to the reflux temperature of the inert solvent used.
  • the reaction time varies depending on the reaction scale, reaction temperature, and the like, and is not constant but may be appropriately selected within the range of several minutes to 48 hours.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • the compound represented by the general formula (3) can be produced by reacting the compound represented by the general formula (3-1) with a halogenating agent in an inert solvent.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction. Examples thereof include alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol; chains such as diethyl ether, tetrahydrofuran, and dioxane.
  • cyclic ethers aromatic hydrocarbons such as benzene, toluene, xylene, esters such as ethyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-imidazolinone
  • polar solvents such as water and acetic acid.
  • halogenating agent used in the reaction examples include fluorine, chlorine, bromine and iodine halogen molecules, halogenated succinimides such as NCS and NBS, halogenated hydantoins such as DIH, and thionyl chloride.
  • the amount of the halogenating agent to be used is generally in the range of 1-fold mol to 5-fold mol with respect to the compound represented by the general formula (3-1).
  • the reaction temperature in this reaction may be appropriately selected within the range of ⁇ 30 ° C. to the reflux temperature of the inert solvent used.
  • the reaction time varies depending on the reaction scale, reaction temperature, and the like, and is not constant but may be appropriately selected within the range of several minutes to 48 hours.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • Me represents a methyl group
  • Et represents an ethyl group
  • n-Pr represents a normal propyl group.
  • Physical properties indicate melting point (° C.) or NMR.
  • the agricultural and horticultural insecticide containing the condensed heterocyclic compound represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is various agricultural and forestry and horticulture that harms paddy rice, fruit trees, vegetables, other crops, and flowers. Suitable for controlling pests such as stored pests, sanitary pests, nematodes and the like.
  • Examples of the pests or nematodes include the following. Lepidoptera (Lepidoptera) pests such as Parasa consocia, Redwood (Anomis mesogona), Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, African exotic empti (Spod) (Hyphantria cunea), Awanoiga (Ostrinia furnacalis), Ayayoto (Pseudaletia separata), Iga (Tinea translucens), Bactra furfuryla, Parnara guttata, Ira inferens), Brachmia triannulella, Monema flavescens, Iraqusinu Waiba (Trichoplusia ni), Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Males flamingo (Helicoverpa armigera) Phararodonta man
  • Hemiptera pests, for example, Nezara antennata, red beetle (Stenotus rubrovittatus), red beetle (Graphosoma rubrolineatum), red beetle (Trigonotylus coelestialium), Aeschynteles maculatus), red beetle (Creontiades pallidifer), red beetle bug (Dysdercus cingulatus), red beetle (Chrysomphalus ficus), red beetle (Aonidiella aurantii), red crab beetle (Graptops) Scale insects (Icerya purchasi), Japanese beetle (Piezodorus hybneri), Japanese beetle (Lagynotomus elongatus), Japanese white-winged beetle (Thaia subrufa), Japanese black beetle (Scotinophara luridaito
  • Oak beetle (Aguriahana quercus), Kasumi beetle (Lygus spp.), Kabawa tofu aphids (Euceraphis punctipennis), citrus scales (Andaspis kashiius), citrus scales (Coccus pseudomagnolia velvet) , Chestnut beetle (Galeatus spinifrons), Chrysanthemum aphid (Macrosiphoniellabornsanborni), Buprestidae (Aonidiella citrina), Hedgehog beetle (Halyomorpha mista), Stephanitis fasciicaza ⁇ L , Cricket lice (Trioza quercicola), walnut grasshopper (Uhlerites latius), grape leaf hopper (Erythroneura comes), black-footed bug (Paromius exiguus), black-footed bug (Duplaspidio) tus claviger, Nephotettix nigropic
  • Radish aphids (Brevicoryne brassicae), soybean aphids (Aphis glycines), beetle leaf beetles (Leptocorisa oratorius), beetle aphid (Nephotettix virescens), beetle aphids (Uroeucon formosanum), emisto ), Chacanata scale insects (Lecanium persicae), Chanokurohushi scale insects (Parlatoria theae), Chano mare scale insects (Pseudaonidia paeoniae), Emporasca onukii, Chabanae aphid (Plautne phirus) ), Tulip beetle aphid (Macrosiphum euphorbiae), azalea (Stephanitis pyrioides), horn beetle (Ceroplastes ceriferus), camellia beetle (Parlatoria camelliae
  • Aphrophora costalis Japanese cypress (Lygus disponsi), Japanese sword turtle (Lygus saundersi), Japanese pine beetle (Crisicoccus pini), Japanese pine beetle (Empoasca bietis), Matsumoto mori Cic phi , Markopram (Megacopta punctatissimum), Marsyla horn beetle (Eysarcoris guttiger), citrus scale insect (Lepidosaphes beckii), citrus leaf moth (Diaphorina citri), citrus aphid (Toxoptera citricidus), mandarin citri), citrus whitefly (Aleurocanthus spiniferus), citrus leafworm (Pseudococcus citriculus), citrus leafhopper (Zyginella citri), citrus leafhopper (Pulvinaria citricola), mandarin orange Scale insect (Coccus discrepans), citrus scale insect (Pseudaonidia du
  • Coleoptera (Coleoptera) pests include, for example, Xystrocera globosa, Aobaarie-hane-kakushi (Paederus fuscipes), Ahanamuri (Eucetonia roelofsi), Azuki beetle (Callosobruchus chinensis), Arimodosium (Hypera postica), rice weevil (Echinocnemus squameus), rice beetle (Oulema oryzae), rice weevil (Donacia provosti), rice weevil (Lissorhoptrus oryzophilus), Weevil (Acanthoscelides obtectus), western corn rootworm (Diabrotica virgifera virgifera), weevil weevil (Involvulus cupreus), weevil (Aulacophora femoralis), pea weevil (Bruchus pisorum) Epilachna viginti
  • Southern corn rootworm (Diabrotica undecimpunctata howardi), Shibaosou weevil (Sphenophorus venatus), Bark beetle (Crioceris quatuordecimpunctata), Japanese weevil (Conotrachelus nenuphar), Japanese horned beetle (Ceuthbo Tobacco beetle (Lasioderma serricorne), Sitona japonicus, Adoretus tenuimaculatus, Tenebrio molitor, Basilepta balyi (Chaetocnema concinna), Anomala ⁇ cuprea, Heptophylla picea, Epilachna vigintioctopunctata, Northern corn rootworm (Diabrotica longicornis), Eucetonia life Scarabaeidae (Agriotes spp.), Himekatsuobushimushi (Attagenus unicolor japonicus), Japanese red
  • Culex pipiens pallens red flies fly (Pegomya hyoscyami), red spider fly (Liriomyza huidobrensis), house fly (Musca domestica), rice flies Flies Fruit flies (Rhacochlaena japonica), fruit flies (Muscina stabulans), fruit flies such as fruit flies (Megaselia spiracularis), giant butterflies (Clogmia albipunctata), mushroom moth (Tipula aino), hormone moth (Pipula) rhynchus), Anopheles sinensis, Japanese flies (Hylemya brassicae), Soybean fly (Asphondylia sp.), Panax fly (Delia platura), Onion fly (Delia antiqua) RRen ), Ceratitis capitata, Bradysia agrestis, sugar beetle fly (P
  • Hymenoptera Pristomyrmex ⁇ ponnes
  • Arbatidae Moneorumium pharaohnis
  • Pheidole noda Athalia rosae
  • Cristoforma Kuriphilus
  • Hornets black bee (Athalia infumata infumata), horned bee (Arge pagana), Japanese bee (Athalia ⁇ japonica), cricket (Acromyrmex spp.), Fire ant (Solenopsis spp.), Apple honey bee (Arlen ali) (Ochetellus glaber) and the like.
  • insects of the order Diptera Hortocoryphus lineosus
  • Kera Gryllotalpa sp.
  • Coago Oxya hyla intricata
  • Cobainago Oxya yezoensis
  • Tosama locust Locusta migrago
  • Oneya Homorocoryphus jezoensis
  • emma cricket Teogryllus emma
  • Thrips examples of thrips of the order Thrips (Selenothrips rubrocinctus), thrips (Stenchaetothrips biformis), Thrips thrips (Haplothrips , Lithrips floridensis, Thrips simplex, Thrips nigropilosus, Helothripes Leeuwenia pasanii), Shiritaku Thrips pasaniae, Citrus Srips citri, Hypothrips chinensis, Soybean Thrips (Mycterothrips glycines), Da Thrips setosus, Thripsrtsaw Thrips hawaiiensis, Haplothrips kurdjumovi, Thrips coloratus , Lilyripa vaneeckei, and the like.
  • mite moths (Leptotrombidium akamushi), Ashinowa spider mite (Tetranychus ludeni), American dock ticks (Dermacentor variabilis), Ichinami spider mite (Tetranychus truncatus), house dust mite (Ornithonyssus bacoti), mite Tetranychus viennensis), ticks (Tetranychus kanzawai), ticks (Rhipicephalus sanguineus) and other ticks (Cheyletus acc malaccensis), stag beetle tick (Tyrophagus putrescent moth) Tick (Dermacentor taiwanicus), Chinese cabbage mite (Acaphylla theavagrans), Chinese dust mite (Polyphagotarsonemus latus), Tomato mite (Aculops lycopersici), Trichoid mite (Ornithonyssus sylvairum), Nami spider mite (
  • Amite termites (Reticulitermes miyatakei), American termites (Incisitermes minor), Termites (Coptotermes formosanus), Termites (Hodotermopsis japonica), Common termites (Reticulitermes termm ants) , Glyptotermes , Nakajima termite (Glyptotermes nakajimai), Nitobe termite (Pericapritermes nitobei), Yamato termite (Reticulitermes speratus) and the like.
  • cockroach Periplaneta fuliginosa
  • German cockroach Blattella germanica
  • Great cockroach Blatta orientalis
  • Greater cockroach Periplaneta brunnea
  • Greater cockroach Blattella lituriplanet (Periplaneta americana) and the like.
  • fleas examples include human fleas (Pulex irritans), cat fleas (Ctenocephalides felis), and fleas (Ceratophyllus gallinae).
  • Nematodes for example, strawberry nematode (Nothotylenchus acris), rice scallop nematode (Aphelenchoides besseyi), red-footed nematode (Pratylenchus penetrans), red-knot nematode (Meloidogyne hapla), sweet potato nematode (Meloidogyne rostochiensis), Javaloid nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), southern nematode nematode (Pratylenchus coffeae), and pterolenchus nematode (Pratylenchus neglectus)
  • mollusks examples include Pomacea canaliculata, Achatina fulica, slug (Meghimatium bilineatum), Lehmannina valentiana, Limax flavus, and Acusta despecta Is mentioned.
  • the agricultural and horticultural insecticide of the present invention has a strong insecticidal effect against tomato kibaga (Tuta absoluta) as other pests.
  • animal parasite ticks Boophilus microplus
  • black tick ticks Raicephalus sanguineus
  • yellow tick ticks Haemaphysalis longicornis
  • yellow ticks Haemaphysalis flava
  • tsurigane tick ticks Haemaphysata tick
  • Tick Haemaphysalis concinna
  • tick Haemaphysalis japonica
  • tuna Haemaphysalis kitaokai
  • tick Haemaphysalis ias
  • tick Ixodes ovatus
  • tick desmite Ticks Dermanyssus, ticks such as Amblyomma testudinarium, Haemaphysalis megaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis gallinae
  • avian mite Ornithonyssus sylviarum
  • fleas to be controlled include, for example, ectoparasite worms belonging to the order Flea (Siphonaptera), more specifically fleas belonging to the family Flea (Pulicidae), Cleaphyllus (Ceratephyllus), etc. .
  • Fleas belonging to the family flea family include, for example, dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis), human fleas (Pulex irritans), elephant fleas (Echidnophaga gallinacea), keops mouse fleas (Xenopsylla cheopis), Leptopsylla segnis), European mouse minnow (Nosopsyllus fasciatus), and Yamato mouse minnow (Monopsyllus anisus).
  • ectoparasites of animals to be controlled include, for example, bovine lice (Haematopinus eurysternus), foal lice (Haematopinus asini), sheep lice (Dalmalinia ovis), bovine lice (Linognathus vituli), pig lice (Haematopinus suis) ), And louses such as head lice (Pediculus capitis), and lice such as dog lice (Trichodectes canis), bullfly (Tabanus trigonus), green hawk (Culicoides schultzei), and blood-sucking twins (Simulium ornatum) Examples include Lepidoptera pests.
  • nematodes such as lungworm, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms, Manson cranioworm, Broad segmented crestworm, Crustacea, multi-headed tapeworms, single-banded tapeworms, and tapeworms such as multi-banded tapeworms, Japanese schistosomiasis, and fluke-like fluke Protozoa such as Toxoplasma and Cryptosporidium.
  • the compound of the present invention can control not only agricultural and horticultural pests but also sanitary pests.
  • the agricultural and horticultural insecticide containing the condensed heterocyclic compound represented by the general formula (I) or a salt thereof of the present invention as an active ingredient damages paddy field crops, field crops, fruit trees, vegetables, other crops, and florets. It has a remarkable control effect on the pests that it gives, so that it matches the time when the occurrence of the pests is predicted, before the occurrence of the pests or when the occurrence is confirmed, nursery facilities, paddy fields, fields, fruit trees, vegetables, etc.
  • the desired effects of the agricultural and horticultural insecticide of the present invention can be obtained by treating the seeds such as crops, seeds such as flower buds, paddy field water, stalks and leaves or soil and other cultivation carriers.
  • Useful plants to which the agricultural and horticultural insecticide of the present invention can be used are not particularly limited, and examples thereof include cereals (eg, rice, barley, wheat, rye, oats, corn, etc.), beans (soybean, Red beans, broad beans, green beans, green beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, peaches, peaches, plums, cherry peaches, walnuts, chestnuts, almonds, bananas, etc.), leaves and fruit vegetables (cabbage, Tomatoes, spinach, broccoli, lettuce, onions, green onions (satsuki, parsley), peppers, eggplants, strawberries, peppers, ladle, leek, etc.
  • cereals eg, rice, barley, wheat, rye, oats, corn, etc.
  • beans soybean, Red beans, broad beans, green beans, green beans, peanuts, etc.
  • fruit trees and fruits apples, citrus fruits, pears, peaches, pe
  • crops for processing (salmon, hemp, beet, hop, sugar cane, sugar beet, olive, rubber, coffee, tobacco, tea, etc.)
  • Cucumbers (pumpkin, cucumber, watermelon, mushroom, melon, etc.), pastures (orchard grass, sorghum, timothy, clover, alfalfa, etc.), turf (Korean turf, bentgrass, etc.), fragrances, etc.
  • the “plant” includes HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, cetoxydim and the like. Also included are plants that have been rendered resistant by classical breeding methods or genetic recombination techniques to resistance to herbicides such as acetyl CoA carboxylase inhibitors, bromoxynil, dicamba, 2,4-D.
  • HPPD inhibitors such as isoxaflutol
  • ALS inhibitors such as imazetapyr and thifensulfuron methyl
  • EPSP synthase inhibitors such as glyphosate
  • glutamine synthase inhibitors such as glufosinate, cetoxydim and the like.
  • plants that have been rendered resistant by classical breeding methods or genetic recombination techniques to resistance to herbicides such as
  • Plants to which tolerance to an acetyl-CoA carboxylase inhibitor has been imparted are Procedures of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci). USA) 87, 7175-7179 (1990).
  • a mutant acetyl CoA carboxylase resistant to an acetyl CoA carboxylase inhibitor has been reported in Weed Science 53, 728-746 (2005).
  • Introducing a plant resistant to an acetyl-CoA carboxylase inhibitor by introducing a mutation associated with imparting resistance into a plant or introducing a mutation associated with imparting resistance into a plant acetyl-CoA carboxylase, and further, chimeric plastic technology (Gura T. et al. 1999.
  • toxins expressed in transgenic plants insecticidal proteins derived from Bacillus cereus or Bacillus popirie; ⁇ - such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis Insecticidal proteins such as endotoxin, VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; Agglutinin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; lysine, corn-RIP, abrin, ruffin, saporin, bryodin Bosome inactivating protein (RIP); steroid metabolic enzymes such as 3-hydroxysteroid,
  • toxins expressed in such genetically modified plants Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, Cry35Ab and other ⁇ -endotoxin proteins, VIP1, VIP2, VIP3 or VIP3A etc.
  • insecticidal protein hybrid toxins partially defective toxins, and modified toxins.
  • Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques.
  • Cry1Ab lacking a part Cry1Ab lacking a part of the amino acid sequence is known.
  • the modified toxin one or more amino acids of the natural toxin are substituted.
  • Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878. , WO 03/052073, and the like.
  • Toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Hemiptera pests, Diptera pests, Lepidoptera pests and nematodes.
  • the agricultural and horticultural insecticides of the present invention can be used in combination with these techniques or systematized.
  • the insecticide for agricultural and horticultural use according to the present invention is used to control various insect pests as they are, or appropriately diluted with water or the like, or suspended in an amount effective for controlling insects or nematodes.
  • pests and nematodes occurring in fruit trees, cereals, vegetables, etc., in addition to spraying on the foliage, seed immersion in seeds, seed dressing, calper treatment Etc.
  • it can be used for nutrient solution in nutrient solution (hydroponics) cultivation, smoke, or trunk injection.
  • the agricultural and horticultural insecticide of the present invention may be used as it is, or appropriately diluted with water or the like, or an amount effective for controlling pests in a place where the occurrence of the pests is predicted.
  • the agricultural and horticultural insecticide of the present invention may be used as it is, or appropriately diluted with water or the like, or an amount effective for controlling pests in a place where the occurrence of the pests is predicted.
  • they can also be used for application to house building materials, smoke, baits, and the like.
  • Seed treatment methods include, for example, a method in which a liquid or solid preparation is diluted or undiluted and the seed is immersed in a liquid state to infiltrate the drug, a solid preparation or liquid preparation is mixed with the seed, Examples thereof include a method of treating and adhering to the surface of the seed, a method of coating the seed by mixing with an adhesive carrier such as resin and polymer, and a method of spraying around the seed simultaneously with planting.
  • the “seed” for performing the seed treatment means a plant body at an early stage of cultivation used for plant propagation. For example, in addition to seeds, bulbs, tubers, seed buds, stock buds, baskets, bulbs, or cuttings are used for cultivation. Mention may be made of plants for vegetative propagation.
  • the “soil” or “cultivation carrier” of the plant when carrying out the method of use of the present invention refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. However, any material that can grow plants may be used, and so-called soil, seedling mats, water, etc. may be used. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, high It may be a molecular substance, rock wool, glass wool, wood chip, bark or the like.
  • a spraying method to crop foliage or stored grain pests, house pests, hygiene pests, forest pests, etc. dilute liquid preparations such as emulsions and flowables or solid preparations such as wettable powders or granular wettable powders with water as appropriate.
  • Examples of application methods to soil include, for example, a method in which a liquid preparation is diluted or not diluted with water and applied to a plant stock or a seedling nursery, etc.
  • a method of spraying to a nursery, etc. a method of spraying powder, wettable powder, granule wettable powder, granule, etc. before sowing or transplanting and mixing with the whole soil, a planting hole, making before planting or planting a plant body
  • Examples include a method of spraying powder, wettable powder, wettable powder, granule, etc. on the strip.
  • the dosage form may vary depending on the time of application such as application at seeding, greening period, application at transplanting, etc., but agents such as powder, granule wettable powder, granules, etc. Apply by mold. It can also be applied by mixing with cultivating soil, and it can be mixed with cultivating soil and powder, granulated wettable powder or granules, for example, mixed with floor soil, mixed with covering soil, mixed into the entire cultivated soil and the like. Simply, the soil and various preparations may be applied alternately in layers.
  • solid preparations such as jumbo agents, pack agents, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields.
  • an appropriate formulation can be sprayed and injected into the soil as it is or mixed with fertilizer.
  • a chemical solution such as emulsion or flowable as a source of water flowing into a paddy field such as a water mouth or an irrigation device, it can be applied in a labor-saving manner along with the supply of water.
  • the plant source of the plant being cultivated In field crops, it can be treated to seeds or a cultivation carrier close to the plant body from sowing to raising seedling.
  • treatment on the plant source of the plant being cultivated is suitable.
  • a spray treatment using a granule or a irrigation treatment in a liquid of a drug diluted or not diluted with water can be performed. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow.
  • the irrigation treatment of the liquid drug or the granule spraying treatment to the seedling nursery is preferred.
  • a granule is treated in a planting hole at the time of planting or is mixed with a cultivation carrier in the vicinity of the transplantation site.
  • the agricultural and horticultural insecticide of the present invention is generally used in a form convenient for use according to a conventional method for agricultural chemical preparations. That is, the condensed heterocyclic compound represented by the general formula (I) of the present invention or a salt thereof is dissolved in an appropriate inert carrier or, if necessary, together with an auxiliary agent in an appropriate ratio.
  • the composition of the present invention can contain, in addition to the active ingredient, additive components usually used in agricultural chemical formulations or animal parasite control agents as required.
  • additive components include a carrier such as a solid carrier and a liquid carrier, a surfactant, a dispersant, a wetting agent, a binder, a tackifier, a thickener, a colorant, a spreading agent, a spreading agent, and an antifreezing agent. , Anti-caking agents, disintegrants, decomposition inhibitors and the like. In addition, you may use a preservative, a plant piece, etc. for an additional component as needed. These additive components may be used alone or in combination of two or more.
  • the solid support examples include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride.
  • liquid carrier examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol
  • polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • Alcohols such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc.
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc.
  • Ethers normal paraffins, naphthenes, isoparaffins, kerosene, mineral oils and other aliphatic hydrocarbons
  • Aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate, etc.
  • Esters lactones such as ⁇ -butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethylsulfoxide, soybean oil, rapeseed oil, Examples thereof include vegetable oils such as cottonseed oil and castor oil, and water. These may be used alone or in combination of two or more.
  • surfactants used as dispersants and wetting agents include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, Polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxye Lenalkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene dio
  • binders and tackifiers include carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6000 to 20000.
  • Polyethylene glycol polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipid (for example, cephalin, lecithin, etc.) cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, cross-linked polyvinylpyrrolidone, maleic acid and styrenes Polymers, (meth) acrylic acid copolymers, half-esters of polycarboxylic alcohol polymers and dicarboxylic acid anhydrides, water soluble salts of polystyrene sulfonic acid, para Fin, terpene, polyamide resins, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, synthetic resin emulsions, and the like.
  • phospholipid for example, cephalin, lecithin, etc.
  • cellulose powder dextrin
  • polyaminocarboxylic acid chelate compound cross-linked polyviny
  • thickener examples include xanthan gum, guar gum, diyutane gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compound, water-soluble polymer such as polysaccharide, high-purity bentonite, fumed silica (fumed Inorganic fine powders such as silica and white carbon.
  • the colorant examples include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.
  • antifreezing agent examples include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
  • Adjuvants for preventing caking and promoting disintegration include, for example, polysaccharides such as starch, alginic acid, mannose, galactose, polyvinylpyrrolidone, fumed silica (fumed silica), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride copolymer, starch / polyacrylonitrile graft copolymer A polymer etc. are mentioned.
  • the decomposition inhibitor examples include desiccants such as zeolite, quicklime and magnesium oxide, antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.
  • desiccants such as zeolite, quicklime and magnesium oxide
  • antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds
  • ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.
  • preservative examples include potassium sorbate, 1,2-benzothiazolin-3-one, and the like.
  • functional aids such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, UV absorbers and other supplements as necessary Agents can also be used.
  • the blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural insecticide of the present invention.
  • 0.01 to 50 parts by weight 0.01 to 50% by weight based on the total weight of the agricultural and horticultural insecticide
  • the amount of the agricultural and horticultural insecticide of the present invention depends on various factors such as purpose, target pests, crop growth status, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application location, application time, etc. Although it varies, the active ingredient compound may be suitably selected from the range of 0.001 g to 10 kg per 10 ares, preferably 0.01 g to 1 kg depending on the purpose.
  • Agricultural and horticultural insecticides of the present invention are pests to be controlled, other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, for the purpose of expanding the appropriate period of control or reducing the dose. It can also be used by mixing with biological pesticides, etc., and can also be used by mixing with herbicides, plant growth regulators, fertilizers, etc., depending on the situation of use.
  • Examples of other agricultural and horticultural insecticides, acaricides, and nematicides used for such purposes include: 3,5-xylylmethylcarbamate (XMC), Bacillus thuringienses (for example, Bacillus thuringienses aizawai, Bacillus thuringienses aizawai) Crystals produced by Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses kurstaki, Bacillus thuringiensis tenebrionis (Bacillus thuringienses tenebrionis) , BPMC, Bt toxin insecticide, chlorfenson (CPCBS), dichlorodiisopropyl ether (DCIP), 3-dichloropropene (DD), DDT, NAC, -4-dimethylsulfamoylphenyl O, O-diethyl phosphoroth
  • Machine oil malathion, milbemycin, milbemycin-A, milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde , Metaflumizone, metamidophos, metam-ammonium, metam-sodium, methiocarb, methidathion (DMTP), methylisothiocyanate, methylneothiocyanate Decanamide (methylneodecanamide), methylparathion (methylparathion), methoxadiazone (metoxadiazone), methoxychlor (methoxychlor), methoxyfenozide (methoforuide) (metofluthrin), methoprene (methoprene), metolcarb (metolcarb), melfluthrin (meperfluthrin) nphos, monocrotophos, monosultap, lambda-cyhalothrin, ryanodine, lu
  • Examples of agricultural and horticultural fungicides used for similar purposes include aureofungin, azaconazole, azithiram, acipetacs, acibenzolar, acibenzolar-S-methyl. ), Azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam, isothianyl (Isotianil), isovaledione, isopyrazam, isoprothiolane, ipconazole, iprodione, iprovalicarb, iprobenfos, imazalil ), Iminoctadine, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, uniconazole, uniconazole-P, mezoleoleech ), Edifenphos, etaconazole, ethaboxam, etirimol
  • herbicides for example, 1-naphthylacetamide, 2, 4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2, 4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, aclonifen, azafenidin, acifluorfen, aziprotryne, azimsulfuron, aslam, acetochlor, Atrazine, atraton, anisuron, anilofos, abiglycine, abscisic acid, amicarbazone, amidosulfuron, amitrole, amino Cyclopyrachlor (aminocyclopyrachlor), aminopyralid (aminopyralid), a Ambuzin, amiprophos-methyl, ametridi
  • Terbacil daimuron, dazomet, dalapon, thiazafluron, thiazopyr, thiencarbazone, thiencarbazone-methyl, thiocarbazil, tiocarbazil Thioclorim, thiobencarb, thidiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmethrin, tetrafluron (Tetrafluron), tenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione ), Delelachlor, terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryn, topramezone, tralkoxydim, trialflam, triaziflam (Triasulfuron), tri-allate,
  • Pretilachlor proxan, proglinazine, procyazine, prodiamine, prosulfalin, prosulfuron, prosulfocarb, propoxahop ( propaquizafop), propachlor, propazine, propanil, propyzamide, propisochlor, prohydrojasmon, propyrisulfuron, propham, Profluazol, profluralin, prohexadione-calcium, propoxycarbazone, propoxycarbazone sodium, propoxydim Bromacil (bromacil), Buromupirazon (brompyrazon), prometryn (prometryn), prometon (prometon), bromoxynil (bromoxynil), bromophenoxy shims (bromofenoxim), bromobutide (bromobutide), Buromoboniru (bromobonil), florasulam (florasulam),
  • biological pesticides include nuclear polyhedrosis virus (NV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), insect pox virus (Entomopoxivirus, EPV) ) And other virus preparations, Monocrosporium matophymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasturia ⁇ pene worm killing Microbial pesticides used as agents, bactericides such as Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis Microbial pesticide to be used in, by using mixed such as biological pesticides utilized as herbicides, such as Xanthomonas campestris (Xanthomonas campestris), the same effect can be expected.
  • NV nuclear polyhedrosis virus
  • GV granulosis virus
  • CPV cytoplasmic polyhedrosis virus
  • examples of biological pesticides include Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusahysrica persimilis), natural enemies such as Amblyseius cucumeris, Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z) -10-tetradecenyl acetate, (E, Z) ) -4,10-tetradecadinyl acetate, (Z) -8-dodecenyl acetate, (Z) -11-tetradecenyl acetate, (Z) -13-icosen-10-one, 14-methyl-1 - May also be used in combination with pheromone agents such as octadecene It is a function.
  • pheromone agents such as octadecene It is a function.
  • Formulation Example 2 Compound (I) of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above is uniformly mixed and pulverized to obtain a powder.
  • Formulation Example 3 Compound (I) of the present invention 5 parts Bentonite and clay mixed powder 90 parts lignin sulfonate 5 parts The above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to form granules.
  • Formulation Example 4 Compound (I) of the present invention 20 parts Kaolin, synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts The above is uniformly mixed and ground to obtain a wettable powder.
  • Control value test against peach aphid (Myzus persicae) Chinese cabbage was planted in a plastic pot having a diameter of 8 cm and a height of 8 cm to breed a peach aphid, and the number of parasites in each pot was investigated.
  • the condensed heterocyclic compound represented by the general formula (I) of the present invention or a salt thereof is dispersed in water and diluted to 500 ppm of chemical solution, sprayed on the stems and leaves of potted Chinese cabbage, air-dried, and then the pot is stored in a greenhouse.
  • the number of parasites of the peach aphid parasitizing each Chinese cabbage on the 6th day after drug spraying was calculated, the control value was calculated from the following formula, and the determination was made according to the following criteria.
  • Ta Number of parasites before spraying in the treated area
  • Ca Number of parasites before spraying in the untreated area
  • C Number of parasites after spraying in the untreated area
  • Test Example 2 Insecticidal test against Japanese brown planthopper (Laodelphax striatella)
  • the condensed heterocyclic compound represented by the general formula (I) of the present invention or a salt thereof is dispersed in water and diluted to a chemical solution of 500 ppm, and rice seedlings (variety: Nipponbare) are added to the chemical solution.
  • rice seedlings variety: Nipponbare
  • Test Example 3 Insecticidal test for Plutella xylostella Sponge seedlings are allowed to lay eggs and lay eggs, and two days after the release, cypress seedlings with spawning eggs are condensed complex represented by the general formula (I) of the present invention
  • the drug containing a ring compound as an active ingredient was immersed in a chemical solution diluted to 500 ppm for about 30 seconds, air-dried, and then allowed to stand in a thermostatic chamber at 25 ° C.
  • the number of hatching insects was investigated, the death rate was calculated according to the following formula, and the determination was made according to the criterion of Test Example 1. 1 ward, 10 heads, 3 systems.
  • the compound according to the present invention has an excellent control effect against a wide range of agricultural and horticultural pests and is useful.

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Abstract

Il est souhaitable de mettre au point un nouveau pesticide agricole et horticole en raison du nombre de nuisibles qui sont résistants aux pesticides existants qui provoquent des dégâts croissants sur les cultures agricoles et horticoles. La présente invention concerne un composé hétérocyclique condensé indiqué par la formule générale (I) (dans la formule, A1, A2 et A3 indiquent un groupe CH ou un atome d'azote, R1 indique un groupe alkyle, etc., R2 indique un groupe halogénoalkyle, etc., R3 et R4 indiquent un atome d'hydrogène, etc., R5 indique un groupe halogénoalkyle, etc., R6 indique un groupe alkyle et m indique 0, 1 ou 2.) ou son sel, un pesticide agricole et horticole comprenant ledit composé en tant que principe actif et un procédé d'utilisation dudit composé.
PCT/JP2014/057214 2013-03-19 2014-03-18 Composé hétérocyclique condensé ou son sel, pesticide pour un usage agricole et horticole contenant ledit composé et son procédé d'utilisation WO2014148451A1 (fr)

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WO2018070502A1 (fr) * 2016-10-13 2018-04-19 日本農薬株式会社 Composé de 1h-pyrrolopyridine, n-oxyde de celui-ci, sel de celui-ci, pesticide à usage agricole et horticole contenant ledit composé, et son procédé d'utilisation
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WO2019162174A1 (fr) 2018-02-21 2019-08-29 Bayer Aktiengesellschaft Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides
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US10667517B2 (en) 2015-08-07 2020-06-02 Bayer Cropscience Aktiengesellschaft 2-(Het)aryl-substituted fused heterocycle derivatives as pesticides
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