WO2014119684A1 - Heterocyclic compound or salt thereof, which is used as pest control agent - Google Patents

Heterocyclic compound or salt thereof, which is used as pest control agent Download PDF

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Publication number
WO2014119684A1
WO2014119684A1 PCT/JP2014/052161 JP2014052161W WO2014119684A1 WO 2014119684 A1 WO2014119684 A1 WO 2014119684A1 JP 2014052161 W JP2014052161 W JP 2014052161W WO 2014119684 A1 WO2014119684 A1 WO 2014119684A1
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group
optionally substituted
substituted
compound
atom
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PCT/JP2014/052161
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French (fr)
Japanese (ja)
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広成 大倉
一樹 北嶌
敦子 河原
健夫 脇田
あゆみ 川▲瀬▼
路一 野村
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三井化学アグロ株式会社
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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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/86—Hydrazides; Thio or imino analogues thereof
    • C07D213/87—Hydrazides; Thio or imino analogues thereof in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • the present invention relates to a heterocyclic compound or a salt thereof used as a pest control agent.
  • Patent Documents 1 to 17 description of compounds similar to the compound of the present invention as insecticides is recognized. However, it is clear that the compound is different from the compound of the present invention.
  • Patent Document 18 recognizes a compound similar to the compound of the present invention as a fungicide. However, it is clear that the compound is different from the compound of the present invention.
  • the objective of this invention is providing the heterocyclic compound or its salt which can be contained as an active ingredient in the pest control agent which has a high insecticidal effect.
  • Another object of the present invention is to provide a heterocyclic compound represented by the general formula (I) or a salt thereof (hereinafter sometimes referred to as “the compound of the present invention”), a method for producing the compound, and effective use of the compound.
  • An object of the present invention is to provide a pest control agent contained as a component and a method for controlling pests using the compound in combination with other insecticides and / or fungicides. Other insecticides and fungicides are different from the compounds of the present invention.
  • the present inventors are a novel compound not described in the literature, and have a remarkably excellent insecticidal effect. Has found a new use. As a result, the present invention has been completed. That is, the present invention includes the following embodiments.
  • G 1 represents a nitrogen atom, a carbon atom, or CH.
  • R 1 is a hydrogen atom, halogen atom, cyano group, nitro group, C1-C6 alkyl group, C2-C6 alkenyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 An alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylsulfonyl group is represented.
  • m represents an integer of 1 to 3, and when m represents an integer of 2 or more, each R 1 may be the same as or different from each other.
  • n represents
  • a 1 represents a carbon atom or a nitrogen atom.
  • a 2 represents a carbon atom or a sulfur atom.
  • a 3 represents a carbon atom or a nitrogen atom.
  • a 4 represents a carbon atom or a nitrogen atom.
  • p represents an integer of 0 to 2.
  • R 2 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1- C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, or C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 It represents a C1-C6 alkyl group substituted with an alkylsulfonyl group, a hydroxy
  • R 5 is a hydrogen atom, C1-C6 alkyl group, C3-C6 cycloalkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 haloalkyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl Group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkylaminocarbonyl group, or a di (C1-C6 alkyl) aminocarbonyl group.
  • R 3 is a hydrogen atom, C1-C6 alkyl group, C3-C6 cycloalkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkoxycarbonyl group, formyl Group, C1-C6 alkylcarbonyl group, C1-C6 alkylaminocarbonyl group or di (C1-C6 alkyl) aminocarbonyl group, or C1-C6
  • R 4 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1 -C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkylaminocarbonyl group, optionally substituted phenylaminocarbonyl group, C1-C6 Haloalkylaminocarbonyl group, di (C1-C6 alkyl) aminocarbonyl group, (C1-C6 alkyl) (C1-C6 haloal
  • C1-C6 alkylaminocarbonyl group an optionally substituted C1-C6 haloalkylaminocarbonyl group (preferably a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkyl group)
  • R 4 is an optionally substituted heterocyclyl group, an optionally substituted furanyl group, an optionally substituted thienyl group, an optionally substituted pyrrolyl group, an optional
  • R 4 is an optionally substituted heterocyclyl group, an optionally substituted furanyl group, An optionally substituted thienyl group, an optionally substituted pyrrolyl group, an optionally substituted pyrazolyl group, an optionally substituted imidazolyl group, an optionally substituted 1,2,3-triazolyl group, a substituted 1,2,4-triazolyl group which may be substituted, oxazolyl group which may be substituted, isoxazolyl group which may be substituted, thiazolyl group which may be substituted, isothiazolyl group which may be substituted, substituted 1,2,3-oxadiazolyl group which may be substituted, 1,2,4-oxadiazolyl group which may be substituted, 1,3,4-optionally substituted Oxadiazolyl group, optionally substituted 1,2,5-oxadiazolyl group, optionally substituted 1,2,5-oxadiazolyl group, optionally substituted 1,2,5-oxadiazolyl
  • a 1 is a nitrogen atom
  • a 2 is a sulfur atom
  • a 3 is a carbon atom
  • R 2 is a methyl group
  • Q is NR 5 and R 5 is a hydrogen atom
  • R 4 is not a methoxycarbonyl group. . ⁇
  • Hy represents any one of the following formulas (B 1 ) to (B 11 ):
  • R 2 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1- C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, or C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 It represents a C1-C6 alkyl group substituted with an alkylsulf
  • Q represents NR 5 and Hy represents the following formulas (B 1 ), (B 2 ), (B 4 ), (B 5 ), (B 6 ), (B 7 ), (B 8 ) or Represents (B 9 )
  • R 2 is the same as above the meaning of, * 2 denotes the point of attachment to G 2.
  • * 2 denotes the point of attachment to G 2.
  • Q represents an oxygen atom
  • Hy represents the following formula (B 1 ), (B 2 ), (B 4 ), (B 5 ), (B 6 ), (B 7 ), (B 8 ) or Represents (B 9 )
  • R 2 is the same as above the meaning of, * 2 denotes the point of attachment to G 2.
  • * 2 denotes the point of attachment to G 2.
  • composition comprising the heterocyclic compound or a salt thereof according to any one of [1] to [6], and an inert carrier or adjuvant.
  • a pest control agent comprising the heterocyclic compound or a salt thereof according to any one of [1] to [6] as an active ingredient.
  • An agricultural and horticultural pest control agent comprising the heterocyclic compound or a salt thereof according to any one of [1] to [6] as an active ingredient.
  • a method of using the drug comprising treating a drug containing an effective amount of the heterocyclic compound or the salt thereof according to any one of [1] to [6] with a useful crop or soil.
  • heterocyclic compound or salt thereof according to any one of [1] to [6] and one of other insecticides and / or fungicides different from the heterocyclic compound or salt thereof A mixture comprising the above.
  • a method for controlling pests comprising treating a useful crop or soil with a drug containing an effective amount of the heterocyclic compound or salt thereof according to any one of [1] to [6].
  • the compound of the present invention realizes an excellent control effect when contained in a pest control agent. It also exhibits excellent control effect when used in combination with other insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, biological pesticides and the like.
  • the compound of the present invention realizes an excellent control effect when contained in a pest control agent.
  • the heterocyclic compound or a salt thereof of the present invention is a heterocyclic compound represented by the following general formula (I) or a salt thereof (the present compound).
  • the pest control agent containing the compound of the present invention as an active ingredient has a high insecticidal effect.
  • the compound of the present invention has the following general formula (I)
  • G 1 represents a nitrogen atom, a carbon atom, or CH.
  • R 1 is a hydrogen atom, halogen atom, cyano group, nitro group, C1-C6 alkyl group, C2-C6 alkenyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 An alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylsulfonyl group is represented.
  • m represents an integer of 1 to 3, and when m represents an integer of 2 or more, each R 1 may be the same as or different from each other.
  • n represents
  • Hy represents the following general formula (B0)
  • a 1 represents a carbon atom or a nitrogen atom.
  • a 2 represents a carbon atom or a sulfur atom.
  • a 3 represents a carbon atom or a nitrogen atom.
  • a 4 represents a carbon atom or a nitrogen atom.
  • p represents an integer of 0-2.
  • q represents 0 or 1;
  • R 2 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1- C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, or C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 It represents a C1-C6 alkyl group substituted with an alkylsulfonyl group, a hydroxyamino group, an
  • G 2 represents the following general formula (IG 2 )
  • R 5 is a hydrogen atom, C1-C6 alkyl group, C3-C6 cycloalkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 haloalkyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl Group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkylaminocarbonyl group, or a di (C1-C6 alkyl) aminocarbonyl group.
  • R 3 is a hydrogen atom, C1-C6 alkyl group, C3-C6 cycloalkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkoxycarbonyl group, formyl Group, C1-C6 alkylcarbonyl group, C1-C6 alkylaminocarbonyl group or di (C1-C6 alkyl) aminocarbonyl group, C1-C6 al
  • R 4 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1 -C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkylaminocarbonyl group, optionally substituted phenylaminocarbonyl group, C1-C6 Haloalkylaminocarbonyl group, di (C1-C6 alkyl) aminocarbonyl group, (C1-C6 alkyl) (C1-C6 haloal
  • C1-C6 alkylaminocarbonyl group an optionally substituted C1-C6 haloalkylaminocarbonyl group (preferably a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkyl group)
  • a sulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylaminocarbonyl group substituted with a C1-C6 haloalkylsulfonyl group preferably a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alky
  • R 4 is optionally substituted heterocyclyl group, optionally substituted furanyl group, optionally substituted thienyl group, optionally substituted pyrrolyl group, or optionally substituted.
  • R 4 is an optionally substituted heterocyclyl group, an optionally substituted furanyl group, or a substituted
  • A1 is nitrogen atom and A2 is sulfur atom and A3 is a methyl group and Q is a carbon atom and R2 is the case of NR 5 and R 5 is a hydrogen atom, R 4 is not a methoxy group. ) Or a salt thereof.
  • Halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • the notation “Ca—Cb (a, b represents an integer of 1 or more)” defines the range of the number of carbon atoms in the substituent described immediately thereafter.
  • C1-C3 is a carbon atom.
  • the number means 1 to 3
  • C2-C6 means 2 to 6 carbon atoms
  • C1-C6 means 1 to 6 carbon atoms.
  • the term “which may be substituted” indicates that the substituent immediately after the word includes both a case where the substituent is further substituted and a case where the substituent is not substituted.
  • the substituent includes a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group.
  • C1-C6 haloalkylthio group C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkylamino group, Phenyl It means.
  • the “C1-C3 alkyl group” refers to a linear or branched alkyl group having 1 to 3 carbon atoms such as methyl, ethyl, n-propyl, i-propyl and the like.
  • the “C1-C4 alkyl group” means, for example, a linear or branched carbon atom such as n-butyl, s-butyl, i-butyl, t-butyl, etc. in addition to the “C1-C3 alkyl group”. Shows up to 4 alkyl groups.
  • C1-C6 alkyl group means, for example, n-pentyl, 2-pentyl, 3-pentyl, neopentyl, n-hexyl, 2-hexyl, 4-methyl-2-pentyl in addition to “C1-C4 alkyl group” And a linear or branched alkyl group having 1 to 6 carbon atoms such as 3-methyl-n-pentyl.
  • C1-C6 haloalkyl group means, for example, monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, 1-fluoroethyl, 2-fluoro Ethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-chloroethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 1-bromoethyl, 2-bromoethyl 2,2-dibromoethyl, 2,2,2-tribromoethyl, 2-iodoethyl, pentafluoroethyl, 3-fluoro-n-propyl, 3-chloro-n-propyl, 3-bromo-n-propyl, 1,3-d
  • C2-C6 alkenyl group refers to an alkenyl group having 2 to 4 carbon atoms having a double bond in a carbon chain such as vinyl, allyl, 2-butenyl, 3-butenyl, etc.
  • Examples of the “C4 haloalkenyl group” include 3,3-difluoro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 2,3-dibromo-2-propenyl, 4 Straight chain having a double bond in a carbon chain substituted by one or more halogen atoms, which may be the same or different, such as 1,4-difluoro-3-butenyl, 3,4,4-tribromo-3-butenyl, etc. Or a branched alkenyl group having 2 to 6 carbon atoms.
  • the “C2-C6 alkynyl group” is, for example, a linear or branched chain having a triple bond in a carbon chain such as propargyl, 1-butyn-3-yl, 1-butyn-3-methyl-3-yl, etc.
  • An alkynyl group having 2 to 6 carbon atoms, and the “C2-C6 haloalkynyl group” includes, for example, a triple bond in a carbon chain substituted by one or more halogen atoms which may be the same or different.
  • a linear or branched alkenyl group having 2 to 6 carbon atoms is, for example, a linear or branched chain having a triple bond in a carbon chain such as propargyl, 1-butyn-3-yl, 1-butyn-3-methyl-3-yl, etc.
  • An alkynyl group having 2 to 6 carbon atoms, and the “C2-C6 haloalkynyl group” includes, for example, a triple bond
  • C3-C6 cycloalkyl group means, for example, a cycloalkyl group having 3 to 6 carbon atoms having a cyclic structure such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl and the like.
  • the “C1-C6 alkoxy group” is, for example, a linear or branched alkoxy group having 1 to 6 carbon atoms such as methoxy, ethoxy, n-propyloxy, isopropyloxy, etc., and “C1-C6 halo”
  • Examples of the “alkoxy group” include trifluoromethoxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 3-fluoro- n-propyloxy, 1,1,1,3,3,4,4,4-octafluoro-2-butyloxy and the like linear or substituted by one or more halogen atoms which may be the same or different
  • a branched haloalkoxy group having 1 to 6 carbon atoms is shown.
  • C1-C6 alkylthio group examples include linear chains such as methylthio, ethylthio, n-propylthio, i-propylthio, cyclopropylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, cyclopropylmethylthio, etc. Or a branched or cyclic alkylthio group having 1 to 6 carbon atoms. *
  • C1-C6 haloalkylthio group examples include trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio, nonafluoro-n- Linear or branched carbon atoms substituted by one or more halogen atoms which may be the same or different, such as butylthio, nonafluoro-s-butylthio, 4,4,4-trifluoro-n-butylthio, etc. 1 to 6 alkylthio groups are shown.
  • C1-C6 alkylsulfinyl group means, for example, straight, branched or cyclic carbon atoms of 1 to 6 carbon atoms such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, cyclopropylsulfinyl, etc. Of the alkylsulfinyl group.
  • C1-C6 haloalkylsulfinyl group examples include trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl and the like.
  • C1-C6 alkylsulfonyl group means, for example, straight, branched or cyclic carbon atoms of 1 to 6 carbon atoms such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, cyclopropylsulfonyl, etc.
  • C1-C6 haloalkylsulfonyl group means, for example, trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro -Represents a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as i-propylsulfonyl.
  • C1-C6 haloalkylsulfonyl group examples include trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl and the like.
  • C1-C6 alkylamino group means, for example, a linear, branched or cyclic carbon atom such as methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, cyclopropylamino, etc. A number 1 to 6 alkylamino groups are shown.
  • the “di-C1-C6 alkylamino group” is, for example, a linear or branched carbon atom number of 1 to 6 which may be the same or different, such as dimethylamino, diethylamino, N-ethyl-N-methylamino and the like And an amino group substituted by two alkyl groups.
  • C1-C6 alkylcarbonyl group refers to a linear, branched or cyclic alkylcarbonyl group having 1 to 6 carbon atoms such as acetyl, propionyl, isopropylcarbonyl, cyclopropylcarbonyl and the like.
  • the “C1-C6 haloalkylcarbonyl group” is, for example, one or more which may be the same or different, such as monofluoroacetyl, difluoroacetyl, trifluoroacetyl, monochloroacetyl, monobromoacetyl, pentafluoropropionyl, heptafluorobutynyl, etc. Or a straight-chain or branched alkylcarbonyl group having 1 to 6 carbon atoms substituted with a halogen atom.
  • C1-C6 alkoxycarbonyl group means, for example, a linear or branched alkoxycarbonyl group having 1 to 6 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl and the like.
  • C1-C6 haloalkoxycarbonyl group means, for example, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, etc.
  • a linear or branched alkoxycarbonyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be different is shown.
  • C1-C6 alkylaminocarbonyl group refers to a linear or branched alkylaminocarbonyl group having 1 to 6 carbon atoms such as methylcarbamoyl, ethylcarbamoyl, isopropylcarbamoyl and the like.
  • the “C1-C6 haloalkylaminocarbonyl group” is the same as, for example, 2-chloroethylcarbamoyl, 2-bromoethylcarbamoyl, 2,2,2-trifluoroethylcarbamoyl, 2,2,2-trichloroethylcarbamoyl, etc.
  • the “di (C1-C6 alkyl) aminocarbonyl group” is, for example, a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms such as dimethylcarbamoyl, ethylmethylcarbamoyl, diethylcarbamoyl, diisopropylcarbamoyl and the like. Represents an aminocarbonyl group having two.
  • (C1-C6 alkyl) (C1-C6 haloalkyl) aminocarbonyl group includes, for example, N- (2-chloroethyl) -N-methylcarbamoyl, N- (2-bromoethyl) -N-methylcarbamoyl, N- (2, One or more halogen atoms which may be the same or different from a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms, such as 2,2-trifluoroethyl) -N-methylcarbamoyl And an aminocarbonyl group having a linear or branched alkyl group having 1 to 6 carbon atoms substituted by
  • Hy preferably represents any one of the following formulas (B 1 ) to (B 11 ).
  • R 2 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, C1 -C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, or C1-C6 alkoxy group, C1- A C6-haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfonyl group, a hydroxyamino group, an acyl
  • Formula (B 11), more preferably from formula (B 1) is a formula (B 9), formula (B 1), (B 2 ), (B 4) , (B 5 ), (B 6 ), (B 7 ), (B 8 ) or (B 9 ).
  • the compound of the present invention may contain one or more asymmetric carbon atoms or asymmetric centers in its structural formula, and there may be two or more optical isomers. And all the mixtures in which they are contained in an arbitrary ratio.
  • the compound of the present invention may have two or more kinds of geometric isomers in the structural formula, but the present invention includes all of the geometric isomers and mixtures containing them in an arbitrary ratio. Is.
  • Preferred embodiments of the compound of the present invention include the following embodiments.
  • G 1 represents a nitrogen atom, a carbon atom, or CH.
  • R 1 is a hydrogen atom, halogen atom, cyano group, nitro group, C1-C4 alkyl group, allyl group, trifluoromethyl group, C1-C2 alkoxy group, methylthio group, methylsulfinyl group, methylsulfonyl group, halomethylthio group Represents a halomethylsulfinyl group or a halomethylsulfonyl group.
  • m represents 0 or 1.
  • n represents 0 or 1.
  • Hy represents the following general formula (B0) (* 2 represents the bonding position to G2; the dotted line represents the bonding position to the ring having N and G 1 ), and the substituent R 2 may be included.
  • Hy preferably represents any one of formulas (B 1 ) to (B 11 ).
  • R 2 is a hydrogen atom, halogen atom, methyl group, halomethyl group, methoxy group, methylthio group, methylsulfinyl group, methylsulfonyl group, halomethylthio group, halo. Represents a methylsulfinyl group or a halomethylsulfonyl group.
  • Hy is more preferably formulas (B 1 ) to (B 9 ), and (B 1 ), (B 2 ), (B 4 ) , (B 5 ), (B 6 ), (B 7 ), (B 8 ) and (B 9 ) are more preferable.
  • G 2 represents the following general formula (IG 2 )
  • Q represents an oxygen atom or NR 5 .
  • R 5 represents a hydrogen atom, a C1-C2 alkyl group, or an allyl group.
  • R 3 represents a hydrogen atom, a C1-C3 alkyl group, or a halomethyl group.
  • R 4 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1 -C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkylaminocarbonyl group, optionally substituted phenylaminocarbonyl group, C1-C6 Haloalkylaminocarbonyl group, di (C1-C6 alkyl) aminocarbonyl group, (C1-C6 alkyl) (C1-C6 haloal
  • C1-C6 alkylaminocarbonyl group an optionally substituted C1-C6 haloalkylaminocarbonyl group (preferably a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkyl group)
  • R 4 is an optionally substituted pyridyl group, an optionally substituted pyrimidinyl group, an optionally substituted 1,2,3-thiadiazolyl group, an optionally substituted
  • a 1 is a nitrogen atom
  • a 2 is a sulfur atom
  • Q is an oxygen atom and n is 0,
  • Optionally substituted pyridyl group optionally substituted pyrimidinyl group, optionally substituted 1,2,3-thiadiazolyl group, optionally substituted 1,2,4-thiadiazolyl group, substituted
  • Optionally substituted isothiazolyl group optionally substituted 1,2,3-oxadiazolyl group, optionally substituted 1,2,4-oxadiazolyl group, optionally substituted 1,3,4-oxadiazolyl group Group, 1,2,5-oxadiazolyl group which may be substituted, 1,3,4-thiadiazolyl group which may be substituted, 1,2,5-thiadiazolyl group which may be substituted in addition, if a 1 is a nitrogen atom and a 2 is a sulfur atom and a 3 are carbon atoms and R2 a methyl group and Q is the NR 5 and R 5 a hydrogen atom
  • R is a hydrogen atom, halogen atom, hydroxy group, cyano group, nitro group, C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1- C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkyl Carbonyl group, C1-C6 alkoxycarbonyl group, C
  • the ester of formula (IV) is first converted to the carboxylic acid of formula (V) using standard methods shown in reaction scheme 1 (see, for example, DE 2221647). Can then be converted to the acid chloride of formula (VI).
  • the compound represented by the formula (VII) can be converted to a ketone compound represented by the formula (II) by reacting with an alkyl metal compound (for example, methylmagnesium bromide).
  • an alkyl metal compound for example, methylmagnesium bromide
  • a compound represented by the formula (II) can be obtained from a ketone. Preferably, it can be synthesized as described in Example 1.
  • the oxime represented by the formula (VIII) according to the present invention can be obtained from the ketone represented by the formula (II) by reaction with hydroxylamine in a solvent (for example, ethanol). Preferably, it can be synthesized as described in Reference Example 1.
  • the oxime of formula (VIII) is then reacted by reaction with a chloropyrimidine substituted in a solvent (eg N, N-dimethylformamide) in the presence of an auxiliary base (eg triethylamine).
  • a chloropyrimidine substituted in a solvent eg N, N-dimethylformamide
  • an auxiliary base eg triethylamine
  • Compounds of formula (I) according to the invention can be obtained. Preferably, it can be synthesized as described in Reference Example 1.
  • the hydrazone represented by the formula (IX) according to the present invention can be obtained from the ketone represented by the formula (II) by reaction with hydrazine in a solvent (for example, ethanol). Then, the present invention is obtained from the hydrazone represented by the formula (IX) by reaction with chloropyrimidine substituted in a solvent (for example, N, N-dimethylformamide) in the presence of an auxiliary base (for example, triethylamine). To obtain a compound of formula (I).
  • the compound represented by the formula (I) according to the present invention can be obtained from the ketone represented by the formula (II) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
  • a solvent for example, ethanol
  • the alcohol represented by the formula (X) can be obtained from the ester represented by the formula (IV) by reaction with a reducing agent (for example, lithium aluminum hydride) in a solvent (for example, tetrahydrofuran) (WO2007). / 39172).
  • a reducing agent for example, lithium aluminum hydride
  • a solvent for example, tetrahydrofuran
  • an aldehyde represented by the formula (XI) can be obtained from the alcohol represented by the formula (X) by reaction with an oxidizing agent (eg manganese dioxide) in a solvent (eg ethyl acetate). Yes (see EP 1186604).
  • an alcohol represented by the formula (XII) can be obtained from the aldehyde represented by the formula (XI) by reaction with an alkylmagnesium chloride in a solvent (for example, tetrahydrofuran) (see US2007 / 244940).
  • a ketone compound represented by the formula (II) can be obtained from an alcohol represented by the formula (XII) by reaction with an oxidizing agent (eg manganese dioxide) in a solvent (eg ethyl acetate). Yes (see EP 1186604).
  • the hydrazide represented by the formula (XIII) is represented by the formula (XIV) using ethyl oxalyl chloride in the presence of a base (for example, triethylamine) in a solvent (for example, N, N-dimethylformamide).
  • a base for example, triethylamine
  • a solvent for example, N, N-dimethylformamide.
  • a sulfurizing agent for example, Lawson's reagent
  • the ketone (XVI) can then be obtained from the ester (XV) by reaction with a metal alkyl compound (eg methyl lithium) (see US 2011/1212949).
  • the oxime represented by formula (XVII) according to the present invention can be obtained from the ketone represented by formula (XVI) by reaction with hydroxylamine in a solvent (for example, ethanol).
  • the present invention can be obtained from the oxime represented by the formula (XVII) by reaction with chloropyrimidine substituted in a solvent (eg, N, N-dimethylformamide) in the presence of an auxiliary base (eg, triethylamine).
  • an auxiliary base eg, triethylamine
  • the compound represented by the formula (I) according to the present invention can be obtained from the ketone represented by the formula (XVI) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
  • the boronic acid represented by the formula (XVIII) is a palladium catalyst (for example, tetrakis (triphenylphosphine) palladium (0)), a base (for example, potassium carbonate) in a solvent (for example, ethylene glycol or dimethyl ether). In the presence, it is converted to a pyridine compound of formula (XIX) using acyl bromopyridine (see Journal of Medicinal Chemistry, 2005, vol. 48, No. 1, 224), preferably in the Examples Can be synthesized as described in 2.
  • a palladium catalyst for example, tetrakis (triphenylphosphine) palladium (0)
  • a base for example, potassium carbonate
  • a solvent for example, ethylene glycol or dimethyl ether
  • the oxime represented by the formula (XX) according to the present invention can be obtained from the pyridylpyridine compound represented by the formula (XIX) by reaction with hydroxylamine in a solvent (for example, ethanol).
  • the present invention can be obtained from the oxime represented by the formula (XX) by reaction with chloropyrimidine substituted in a solvent (for example, N, N-dimethylformamide) in the presence of an auxiliary base (for example, triethylamine).
  • the compound represented by the formula (I) can be obtained. Preferably, it can be synthesized as described in Example 2.
  • the compound represented by the formula (I) according to the present invention can be obtained from the ketone represented by the formula (XIX) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
  • the boronic acid represented by the formula (XVIII) is present in a solvent (eg, ethylene glycol dimethyl ether) in the presence of a palladium catalyst (eg, tetrakis (triphenylphosphine) palladium (0)), a base (eg, potassium carbonate).
  • a palladium catalyst eg, tetrakis (triphenylphosphine) palladium (0)
  • a base eg, potassium carbonate
  • the oxime represented by the formula (XXII) according to the present invention can be obtained from the thiophene compound represented by the formula (XXI) by reaction with hydroxylamine in a solvent (for example, ethanol).
  • the present invention can be obtained from the oxime represented by the formula (XXII) by reaction with chloropyrimidine substituted in a solvent (for example, N, N-dimethylformamide) in the presence of an auxiliary base (for example, triethylamine).
  • a compound of formula (I) can be obtained from the ketone represented by the formula (XXI) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
  • the boronic acid represented by the formula (XVIII) is present in a solvent (eg, ethylene glycol dimethyl ether) in the presence of a palladium catalyst (eg, tetrakis (triphenylphosphine) palladium (0)), a base (eg, potassium carbonate).
  • a palladium catalyst eg, tetrakis (triphenylphosphine) palladium (0)
  • a base eg, potassium carbonate
  • acyl bromofuran see Journal of Medicinal Chemistry, 2005, vol. 48, No. 1, 224.
  • the oxime represented by the formula (XXIV) according to the present invention can be obtained from the pyridylfuran compound represented by the formula (XXIII) by reaction with hydroxylamine in a solvent (for example, ethanol).
  • an oxime of the formula (XXIV) by reaction with a chloropyrimidine substituted in a solvent (eg N, N-dimethylformamide) in the presence of an auxiliary base (eg triethylamine).
  • a compound represented by the formula (I) can be obtained.
  • the compound represented by the formula (I) according to the present invention can be obtained from the ketone represented by the formula (XXIII) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
  • the compound represented by the formula (XXV) is prepared by reacting a palladium catalyst (eg, tetrakis (triphenylphosphine) palladium (0)), a base (eg, In the presence of potassium), it is converted to a thiazole compound represented by the formula (XXVI) using acyl thiazole (see Tetrahedron 2012, vol. 68, 7655). Preferably, it can be synthesized as described in Example 3.
  • the oxime represented by the formula (XXVII) according to the present invention can be obtained from the thiazole compound represented by the formula (XXVI) by reaction with hydroxylamine in a solvent (for example, ethanol).
  • the present invention can be obtained from an oxime represented by the formula (XXVII) by reaction with chloropyrimidine substituted in a solvent (eg, N, N-dimethylformamide) in the presence of an auxiliary base (eg, triethylamine)
  • a solvent eg, N, N-dimethylformamide
  • an auxiliary base eg, triethylamine
  • the compound represented by the formula (I) can be obtained.
  • the compound represented by the formula (I) according to the present invention can be obtained from the ketone represented by the formula (XXVI) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
  • the enamine compound represented by the formula (XXVIII) is represented by the formula (XXIX) using an acid compound in the presence of an oxidizing agent (for example, iodosobenzene) in a solvent (for example, dichloroethane). Converted to the enamine compound (see ol 3025583).
  • an oxidizing agent for example, iodosobenzene
  • a solvent for example, dichloroethane
  • the oxime represented by the formula (XXXI) according to the present invention can be obtained from the oxazole compound represented by the formula (XXX) by reaction with hydroxylamine in a solvent (for example, ethanol).
  • the present invention can be obtained from an oxime represented by the formula (XXXI) by reaction with a chloropyrimidine substituted in a solvent (eg, N, N-dimethylformamide) in the presence of an auxiliary base (eg, triethylamine) To obtain a compound of formula (I).
  • the compound represented by the formula (I) according to the present invention can be obtained from the ketone represented by the formula (XXX) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
  • a pyrazole compound represented by the formula (XXXII) is prepared by using a diamine catalyst in a solvent (for example, N, N-dimethylformamide) in the presence of a metal salt (for example, copper iodide). ).
  • a metal salt for example, copper iodide.
  • the compound represented by the formula (XXXIII) is converted into a carboxylic acid represented by the formula (XXXIV) using a middle hydroxide (eg, lithium hydroxide) of a solvent (eg, methanol / water).
  • a chlorinating agent eg thionyl chloride
  • the oxime represented by the formula (XXXVIII) according to the present invention can be obtained from the ketone compound represented by the formula (XXXVII) by reaction with hydroxylamine in a solvent (for example, ethanol).
  • the present invention can be obtained from an oxime represented by the formula (XXXVIII) by reaction with chloropyrimidine substituted in a solvent (eg, N, N-dimethylformamide) in the presence of an auxiliary base (eg, triethylamine) To obtain a compound represented by the formula (I).
  • the compound represented by the formula (I) according to the present invention can be obtained from the ketone represented by the formula (XXXVII) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
  • the target product may be isolated from the reaction system according to a conventional method after completion of the reaction, but may be purified by operations such as recrystallization, column chromatography, and distillation as necessary. Can do.
  • Tables 1 to 4 below show representative compounds and reference compounds of the compounds of the present invention represented by the general formula (I), which are active ingredients of the pesticidal agent of the present invention, as exemplary compounds. Inventive compounds are not limited to these exemplified compounds of the present invention.
  • n- represents normal
  • Me represents a methyl group
  • Et represents an ethyl group
  • n-Pr represents a normal propyl group
  • i-Pr represents an isopropyl group
  • N-Bu represents a normal butyl group
  • i-Bu represents an isobutyl group
  • s-Bu represents a secondary butyl group
  • t-Bu represents a tertiary butyl group
  • H represents a hydrogen atom
  • O represents an oxygen atom
  • S represents a sulfur atom
  • C represents a carbon atom
  • N represents a nitrogen atom
  • F represents a fluorine atom
  • Cl represents a chlorine atom
  • Br is a bromine atom
  • I is an iodine atom
  • CF 3 is a trifluoromethyl group
  • MeS is a methylthio group
  • MeSO is a methylsulfinyl group
  • MeSO 2 is methyl.
  • the compound of the present invention exhibits a controlling effect against pests to be controlled in various agricultural scenes that damage agricultural and horticultural crops and trees. Therefore, this invention compound turns into the pest control agent which has a high insecticidal effect, and the agricultural and horticultural pest control agent by containing this invention compound mentioned above as an active ingredient. Moreover, this invention compound can prevent the damage by pests, such as agricultural pests which generate
  • this invention compound shows a control effect with respect to insects, such as a wood-eating insect, which harms wood, such as a building, furniture, and storage wood. Moreover, this invention compound has a control effect with respect to the sanitary insect pest which has a bad influence in human living environment, such as a house. Moreover, this invention compound has a control effect with respect to the external or internal parasite of a mammal and birds. Moreover, it is possible to effectively control pests such as mites, crustaceans, molluscs, and nematodes that occur and harm in the same scene at low concentrations.
  • insects, mites, crustaceans, molluscs and nematodes that can be controlled using the compounds of the present invention include, for example, Adenophyes honmai and Adoxophies orana facita.
  • apple Mont moth (Archips breviplicanus), apple co-sink bur (Grapholita inopinata), Mi someone summer fruit moth (Archips fuscocupreanus), oriental fruit moth (Grapholita molesta), Chahamaki (Choristoneura magnanima), soybean pod borer, Leguminivora glycinivorella (Leguminivora glycinivorella), Kuwahimehamaki (Olethreutes ori), apple moth subfraction (Caloptilia zachrysa), apple Hime sink Lee (Argyresthia conjugella), Nashihosoga (Spulerrina astaurota), beans Hime Saya insect moth (Matsumuraeses phaseoli), Tobihamaki (Pandemis heparana
  • Pepper leaf beetle (Arboridia apicalis), Green leafhopper (Balcrutha saltuella), Pepper leaf beetle (Epicaanthus stamineus), Potato leaf abalone (Empoasca pea) , Peanut leafhopper (Empoasaka sakaii), leafhopper leafhopper (Macrosteles striifrons), leafhopper leafhopper (Nephotettix multiplinceps), cotton-free hopper (Psuedatomososerissera tossera tossera serisser seraistosera serissertosera tossera serasto elphax striatella), brown planthopper (Nilaparvata lugens), Sejirounka (Sogatella furcifera), Diaphorina citri (Diaphorina citri), Nashikijirami (Psylla pyrisuga), mandarin orange spiny whitefly (Aleurocanthus spiniferus), silverleaf whitefly (B
  • Cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), core Oh flower chafer (Gametis jucunda), Nagachakogane (Heptophylla picea), Japanese beetle (Popillia japonica), Colorado potato beetle (Lepinotarsa decemlineata), Mexican beat beetle (Epilachna varivestis), crew neck Melanotus fortumi, Melanus tamsuyensis, Tobacco beetle (Lasiderma serricorne), Japanese horned beetle (Lyctusbrunneus), Matsukikushi omicus piniperda), Naga Shinkuimushi (Rhizopertha dominica), Hime Hirata Keshikisui (Epuraea domina), bean beetle (Epilachna varivestis), the beetle, Epilachn
  • Hirazuhanaazamiuma (Frankliniella intonsa), Yellow Hana thrips (Thrips flavus), western flower thrips (Frankliniella occidentalis), Croton thrips (Heliothrips haemorrhoidalis), yellow tea thrips (Scirtothrips dorsalis), southern thrips (Thrips palmi), green onion thrips (Thrips tabaci ), Coleoptera thrips (Ponticulotrips diospyrosi), etc.
  • Soybean pod gall midge (Asphondylia yushimai), wheat red gall midge (Sitodiplosis mosellana), melon fly (Bactrocera cucurbitae), oriental fruit fly (Bactrocera dorsalis), the Mediterranean fruit fly (Ceratitis capitata), rice Hime leafminer (Hydrellia griseola), cherry fruit fly (Drosophila suzukii), rice Leafhopper (Agromyza oryzae), leafworm (Chromatomia horticola), eggplant leaffly (Liriomyza bryoniae), leafhopper (Liriomyza chinensis), Mato leafminer (Liriomyza sativae), legume leafminer (Liriomyza trifolii), seedcorn maggot (Delia platura), onion maggot (Delia antique), sugar beet diving Hana fly (Pegomya cunicularia), Apple Maggot (Rhagoletis pomon
  • Kurihabachi (Apethymus kuri), Kaburahabachi (Athalia rosae), Chu range sawfly (Arge pagana), Matsunokihabachi (Neodiprion sertifer), Kuritamabachi (Dryocosmus kuriphilus), army ant (Eciton burchelli, Eciton schmitti), Camponotus japonicus (Camponotus japonicus), Asian giant hornet (Vespa mandarina, bulldog ant (Myrmecia spp.), fire ant (Solenopsis spp.), pharaoh ant (Monomomorium pharaonis), etc.
  • Coleopterous insects such as the white-headed beetle (Onychiurus folsomi), the siberian white-headed beetle (Onychiurus sibiricus), and the burdock beetle (Bourletiella hortensis),
  • Black-eye cockroach Periplaneta fuliginosa
  • Japanese cockroach Periplaneta japonica
  • German cockroach Blattella germanica
  • American cockroach Periplaneta americana
  • Termite insects such as termites (Coptothermes formosanus), Yamato termites (Reticulitermes supertus), Taiwan termites (Odontotermes formosanus),
  • Cat fleas (Ctenocephalidae felis), dog fleas (Ctenocephalides canis), chicken fleas (Echidnophaga gallinacea), human fleas (Pulex iriritans), insects of the mosquito, etc.
  • Insects such as chicken lice (Mecananthus stramineus), bovine lice (Bovicola bovis),
  • Lice insects such as cattle lice (Haematopinus eurysternus), pig lice (Haematopinus suis), cattle white lice (Linognathus vituli), kelp cause lice (Solenopotes capillatus), etc.
  • Dust mites such as cyclamen dust mites (Phytonemus pallidus), chano mite mites (Polyphagotarsononemus latus), and mites (Tarsonmus bilobatus), Spider mites (Penthaleus erythrocephalus), wheat mites (Penthaleus major), etc., Rice spider mites (Oligonychus shinkajii), citrus red spider mite (Pananychus citri), red spider mite (Pananychus ulmi), tick mite (Tananychus urticae), Tetranichus kanzawai Tea Roh Naga rust mite (Acaphylla theavagrans), Tulip rust mite (Aceria tulipae), tomato rust mite (Aculops lycopersici), mandarin orange rust mite (Aculops pelekassi), apple rust mite (Aculus convincedendali), false pear rust mite (Eriophyes chi
  • the compound of the present invention Since the compound of the present invention has a remarkable controlling effect on pests that damage useful crops such as paddy field crops, field crops, fruit trees, vegetables, other crops, and flowers, the occurrence of pests is predicted.
  • the paddy field, fields, fruit trees, vegetables, other crops, flower paddies and other paddy water, stalks and leaves, or the soil of the present invention are processed before or after the occurrence of pests.
  • the effect as a pest control agent is acquired.
  • the compound of the present invention has a remarkable control effect against stored pests and the like generated during storage of harvested products. That is, a pest control agent comprising the compound of the present invention as an active ingredient is harvested by spraying, smearing, coating, dipping, dressing, fumigation / fumigation, pressurized injection, etc. What is necessary is just to perform a post (post harvest) process.
  • the compound of the present invention By applying the compound of the present invention to plant seeds, damage by pests such as agricultural pests generated on the plant after sowing can be prevented. That is, a pest control agent containing the compound of the present invention as an active ingredient is sprayed, smeared, or dipped on a plant seed in an amount effective for pest control as it is, or appropriately diluted with water or suspended. Alternatively, the compound of the present invention may be brought into contact with the plant seeds by treatment such as dressing. In this case, the plant seeds refer to those that store nutrients for germination of young plants and are used for agricultural reproduction.
  • seeds such as corn, soybeans, red beans, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, sweet pea, pumpkin, sugar cane, tobacco, sweet pepper, rape, sweet potato , Seed seeds such as konjac, edible lily, bulbs such as tulips and seed balls such as raccoon.
  • the compound of the present invention has a remarkable control effect against wood pests such as termites, oyster beetles, moth beetles, beetles, longhorn beetles, etc. Can control pests.
  • the compound of the present invention exhibits a control effect against various pests, and has an excellent control effect as an insecticide or acaricide at a low dose, in addition to the effect of protecting useful crops, greatly reducing the burden on the environment. There is an effect to contribute.
  • an inert carrier which is a suitable solid carrier or liquid carrier, and if desired, a surfactant, penetrant, spreading agent, thickener, freezing agent as an auxiliary agent.
  • An inhibitor, a binder, an anti-caking agent, a disintegrant, an antifoaming agent, an antiseptic and an anti-decomposition agent, etc. are added, and a liquid agent, an emulsion, a wettable powder, Water solvent, water dispersible granule, water soluble granule, suspension concentrate, emulsion (concentrated emulsifier), water soluble powder, water dispersible granule, water soluble granule, water suspension concentrate.
  • any of the above dosage forms can be provided by being enclosed in a water-soluble package such as a water-soluble capsule and a bag of a water-soluble film.
  • the compound of the present invention it is preferable to make a composition in which the compound of the present invention and an inert carrier or the above-mentioned auxiliary agent are mixed.
  • the inert carrier that can be used in the present invention may be either solid or liquid.
  • materials that can be used as a solid inert carrier include soybean powder, cereal powder, wood powder, bark powder, saw powder, tobacco stem powder, walnut shell powder, bran, fiber powder, residue after extraction of plant extracts, Synthetic polymers such as pulverized synthetic resins, clays (eg kaolin, bentonite, acid clay), talc (eg talc, pyrophyllide, etc.), silicas (eg diatomaceous earth, silica sand, mica, white carbon (hydrous finely divided silicon, hydrous) Synthetic high-dispersion silicic acid called silicic acid, some of which contain calcium silicate as the main component.]), Activated carbon, sulfur powder, pumice, calcined diatomaceous earth, brick ground, fly ash, sand, calcium carbonate, calcium phosphate, etc.
  • Synthetic polymers such as pulverized synthetic resins, clays (eg
  • Examples thereof include inorganic mineral powders, chemical fertilizers such as ammonium sulfate, phosphorous acid, ammonium nitrate, urea, and ammonium chloride, and compost. These are used alone or in the form of a mixture of two or more.
  • the material that can be a liquid inert carrier is selected from those having solvent ability itself and those that can disperse an active ingredient compound with the aid of an auxiliary agent without having solvent ability.
  • the following carriers can be exemplified, but these are used alone or in the form of a mixture of two or more.
  • Examples of materials that can be used as a liquid inert carrier include water, alcohols (eg, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.) ), Ethers (eg, diethyl ether, dioxane, cellosolve, diisopropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (eg, kerosene, mineral oil, etc.), aromatic hydrocarbons (eg, benzene, toluene, xylene, solvent naphtha, alkyl) Naphthalene etc.), halogenated hydrocarbons (eg dichloromethane, chloroform, carbon tetrachloride, chlorobenzene etc.), est
  • dimethylformamide, diethylformamide, dimethylacetamide, etc. can be exemplified nitriles (e.g. acetonitrile, etc.).
  • nitriles e.g. acetonitrile, etc.
  • These solid and liquid carriers may be used alone or in combination of two or more.
  • the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono or di) phenyl ether, polyoxyethylene (mono, di or tri) styryl phenyl ether, polyoxyethylene polyoxypropylene Block copolymer, polyoxyethylene fatty acid (mono or di) ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, castor oil ethylene oxide adduct, acetylene glycol, acetylene alcohol, ethylene oxide adduct of acetylene glycol, ethylene of acetylene alcohol
  • Nonionic surfactants such as oxide adducts and alkyl glycosides, alkyl sulfate esters, alkylbenzene sulfonates, lignin sulfonic acids , Alkylsulfosuccinate, naphthalenesulfonate, alkylnaphthalenesulfon
  • the amount used varies depending 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. It is preferably used at a concentration of 0.0001 to 5000 ppm, preferably 0.01 to 1000 ppm.
  • the application amount per 10a is generally 1 to 300 g as an active ingredient.
  • the amount of the active ingredient of the compound represented by the general formula (I) of the present invention is 0.1 to 90% by weight, preferably 3 to 90% by weight, more preferably 5 to 90% by weight, still more preferably 5 to 50% by weight, most preferably 5-20% by weight.
  • the amount of the active ingredient of the compound represented by formula (I) of the present invention is usually 0.1 to 20% by weight for powders, 5 to 50% by weight for emulsions, 3 to 90% by weight for wettable powders, and granules. Is 0.1 to 20% by weight, 5 to 90% by weight for flowable preparations, and 3 to 90% by weight for granular wettable powders.
  • the amount of carrier in each dosage form is usually 60 to 99.9% by weight for powders, 40 to 95% by weight for emulsions, 10 to 90% by weight for wettable powders, and 80 to 99.9% by weight for granules. And 10 to 95% by weight for flowable preparations and 10 to 90% by weight for granular wettable powders.
  • the amount of the adjuvant is usually 0.1 to 20% by weight for powders, 1 to 20% by weight for emulsions, 0.1 to 20% by weight for wettable powders, 0.1 to 20% by weight for granules, and
  • the flowable preparation is 0.1 to 20% by weight, and the granule wettable powder is 0.1 to 20% by weight.
  • the compound of the present invention has a remarkable control effect against sanitary pests such as Diptera pests (Acaeca, Chicaeka, Chironae, houseflies, butterflies, cattle fly, etc.), reticulate pests (Chebrobella, black cockroach, American cockroach, etc.) Is. Furthermore, the compound of the present invention is used as an anthelmintic agent for arthropods that cause direct harm, or for arthropods that are disease vectors, against oils, Emulsions, wettable powders, injection, irrigation, application, dusting, fumigants, mosquito coils, self-burning smokes, chemical reaction fumes, etc.
  • sanitary pests such as Diptera pests (Acaeca, Chicaeka, Chironae, houseflies, butterflies, cattle fly, etc.), reticulate pests (Chebrobella, black cockroach, American cockroach, etc.) Is.
  • the compound of the present invention is used as an anthelmin
  • the preparations in these use forms can exist as a mixture with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists. It is appropriate that the preparation of the present invention contains the compound of the present invention in a total amount, for example, 0.0001 to 95% by mass.
  • the compound of the present invention can control external or endoparasites of mammals and birds other than humans such as domestic animals and pets, such as cat fleas, dog fleas, spider mites, and Filariidae nematodes.
  • Control of ectoparasites and endoparasites can be achieved by oral administration, parenteral administration or transdermal administration.
  • Oral administration includes a small amount of the compound of the present invention in a meal, feed, or the like, or an oral administration agent such as a pharmaceutical composition that can be taken orally, such as a pharmaceutically acceptable carrier and a coating substance.
  • the beverage When administered orally as a medicinal drinking water, the beverage is usually dissolved, suspended or dispersed in a suitable non-toxic solvent or water with a suspending or wetting agent such as bentonite or other excipients. is there.
  • medicinal drinking water also contains an antifoaming agent.
  • the medicinal drinking water formulation can generally contain 0.01 to 1.0% by mass, preferably 0.01 to 0.1% by mass of the compound of the present invention.
  • capsules, pills or tablets containing a predetermined amount of the active ingredient are usually used.
  • These forms of use are obtained by intimately mixing the active ingredient with suitably finely divided diluents, fillers, disintegrants and / or binders such as starch, lactose, talc, magnesium stearate, vegetable gums and the like.
  • Such dry solid unit use formulations can vary widely in the anthelmintic mass and content depending on the type of host animal being treated, the degree of infection and the type of parasite and the body weight of the host.
  • When administered by animal feed it can be dispersed homogeneously in the feed, used as a top dressing or in the form of pellets.
  • the compound of the present invention contains, for example, 0.0001 to 0.05% by mass, preferably 0.0005 to 0.01% by mass, in the final feed. You can also.
  • transdermal administration it may be administered as a transdermal agent such as spray, powder, grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo, or the like.
  • a transdermal agent such as spray, powder, grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo, or the like.
  • a device for example, a collar, a medallion, an ear tag, etc.
  • 0.0001 to 0.1% by mass preferably 0.001 to 0.01% by mass of the compound of the present invention is administered. Good.
  • a liquid carrier vehicle can be administered parenterally to animals by intragastric, intramuscular, intratracheal or subcutaneous injection.
  • the active compounds are preferably mixed with suitable vegetable oils, such as peanut oil, cottonseed oil.
  • suitable vegetable oils such as peanut oil, cottonseed oil.
  • Such a formulation can generally contain 0.05 to 50% by mass, preferably 0.1 to 5.0% by mass of the compound of the present invention. It can also be administered topically by mixing with a suitable carrier such as dimethyl sulfoxide or a hydrocarbon solvent. This formulation is applied directly to the external surface of the animal by spraying or direct injection.
  • the compound of the present invention exhibits an excellent control effect even when used as a mixture of the compound of the present invention and one or more of other insecticides and / or fungicides different from the compound of the present invention. is there.
  • other insecticides and / or fungicides include other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, biological pesticides, and the like.
  • Examples of the compound that can be combined with the compound of the present invention in the pest control mixture of the present invention include insecticides, acaricides, pyrethroid compounds, organophosphorus compounds, oxime carbamate compounds as nematicides , Carbamate compounds, neonicotinoid compounds, diacylhydrazine compounds, benzoyl urea compounds, juvenile hormone compounds, cyclodiene organochlorine compounds, 2-dimethylaminopropane-1,3-dithiol compounds, amidine compounds , Phenylpyrazole compounds, organotin compounds, METI compounds, benzylate compounds, allylpyrrole compounds, dinitrophenol compounds, anthranyl diamide compounds, oxadiazine compounds, semicarbazone compounds, tetronic acid compounds , Carbamoyltriazole compounds, tetrazine compounds, and the like.
  • bactericides include strobilurin compounds, anilinopyrimidine compounds, azole compounds, azole compounds, dithiocarbamate compounds, phenyl carbamate compounds.
  • Acrinathrin, allethrin [(1R) -isomer], bifenthrin, bioallethrin, bioarethrin S-cyclopentenyl isomer, S-cyclopentenyl isomer, S-cyclopentenyl isomer, S Cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin (lamb cythothrin) (Cypermethrin), alpha-cypermethrin (beta-cypermethrin), seta-cypermethrin (zeta-cypermethrin (zeta-cypermethrin)) ) -Trans-isomer] (cyphenothrin [(1R) -trans-isomer]), deltame
  • Oxime compounds such as phosphocarb, alaniccarb, butocarboxim, butoxycarboxim, thiodicarb, thiophanox, and thiophanox
  • MPMC xylylcarb
  • phenothiocarb xylylcarb
  • Diacylhydrazine compounds such as chromafenozide, halofenozide, methoxyphenozide, tebufenozide, and the like; Bistrifluron, chlorfluazuuron, diflubenzuron, flucycloxuron, flufenoxuron, hexafluururon, hexafluururon ), Benzoylurea compounds such as noviflumuron, teflubenzuron, triflumuron, Phenoxycarb, hydroprene, quinoprene, methoprene, pyriproxyfen, methoprene, hydroprene, young juvenile hormone, etc.
  • Cyclodiene organochlorine compounds such as chlordane, endosulfan, lindane (gamma-HCH), dienochlor, and the like; 2-dimethylaminopropane-1,3-dithiol compounds such as Cartap hydrochloride, thiocyclam, Amidine-based compounds such as amitraz; Phenylpyrazole compounds such as etiprole, fipronil, acetoprole, etc., Organotin compounds such as azocyclotin, cyhexatin, fenbutatin oxide, and the like, METI compounds such as fenazaquin, fenpyroximate, pyridaben, pyrimidifene, tebufenpyrad, tolfenpyrad, etc.
  • Benzylate compounds such as bromopropyrate, Allylpyrrole compounds such as chlorfenapyl, Dinitrophenol compounds such as DNOC and binapacryl; Anthranyl diamide compounds such as chlorantaniprole and cyantraniprole, Oxadiazine compounds such as indoxacarb, semicarbazone compounds such as metaflumizone, Tetronic acid compounds such as spirodiclofen, spiromesifen, and spirotetramat; Carbamoyltriazole compounds such as triazamate, Tetrazine compounds such as diflovidazin,
  • iodide Caranjin, MB-599 (verbutin), mercuric chloride, metham, methoxychlor, methyl isothiocyanate, pentachlorophenol (pentachlorophosphine) , Piperonyl butoxide, polynactin complex, BPPS (propargite), pymetrozine, pyrethrins, pyridyl (roS), pyridalyl (2,3,3,3-tetrachloropropyl) ether), sabadilla, spinosad, spinetoram, sulcofuron salt (sulcofuron-sodium), sulfluramide, tetradiphone (Tetradifon), thiosultap, tribufos, aldrin, amidithione, amidethioate, aminocarb, amiton, amit Azotoate ), Polysulfide barium, Bayer 22408, Bayer
  • Strobilurin-based compounds such as azoxystrobin, cresoxime-methyl, trifloxystrobin, methminostrobin, oryastrostrobin
  • Anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil, etc., Triadimefone, bittertanol, triflumizole, metconazole, propiconazole, microconil, penconazole, fluconazole, penconazole, fluconazole.
  • Azole compounds such as tebuconazole, hexaconazole, prochloraz, and simeconazole, Quinoxaline compounds such as quinomethionate, Dithiocarbamate compounds such as manneb, zineb, mancozeb, polycarbamate, and propineb, Phenyl carbamate compounds such as dietofencarb, Organochlorine compounds such as chlorothalonil and quintozen, Benzimidazole compounds such as benomyl, thiophanate-methyl, carbendazole, and the like; Phenylamide compounds such as metalaxyl, oxadixyl, ofurase, benalaxyl, furalaxyl, cyprofuram, and the like; Sulfenic acid compounds such as dichlorfluanid, Copper-based compounds such as cupric hydroxide and copper oxyquinoline (oxine-copper); Isoxazole compounds such as hydroxyis
  • Chlorpicrin ethylene dibromide (EDB), sulfuryl fluoride, acrylonitrile, bis (2-chloroethyl) ether, 1-bromo-2-chloroethane, 3-bromo-1-chloroprop-1 -Ene, bromocyclen, carbon disulfide, carbon tetrachloride, carbam sodium salt, nemadectin, aluminum phosphide, etc.
  • Bacillus thuringiensis delta endotoxin Bacillus thuringiensis delta endotoxin (Bacillus thuringiensis delta-endotoxin), borax, calcium polysulfide, cryolite, cytokinin, thiotinin, ethanol Potassium oleate, sodium oleate, machine oil, sulfur, tar oil, anabasine, morantel tartrate, insecticide (Pyrethrum), nicotine sulfate, rapeseed oil, soybean reticin, starch, hydroxypropyl starch, fatty acid glycol (decylolglycol) natural product compounds such as propylene glycol fatty acid ester, diatomite, Bacillus thuringiensis,
  • the compound represented by the following general formula (AA) and a salt thereof examples thereof include compounds and compounds represented by the following general formula (EE).
  • the definition of substituents such as C1 to C6 alkyl groups in the following formula is the same as the definition of C1 to C6 alkyl groups and the like described for the substituents R 1 , R 2 , R 5 and Hy of the compound of the present invention.
  • the compound represented by general formula (AA) is as follows.
  • R a1 represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group
  • R a2 represents a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C2 to C6 alkenyl group
  • R a6 represents a group represented by the formula C—R a3 or a nitrogen atom.
  • R a3 and R a4 each independently represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C7 cycloalkyl group, a cyano group, an optionally substituted phenyl group, a substituted Represents an optionally substituted heterocyclyl group, and an optionally substituted phenoxy group.
  • the compounds represented by (BB) are as follows.
  • R c1 represents an optionally substituted pyridyl group or an optionally substituted thiazolyl group
  • Y c1 represents a halogen atom, a C1 to C6 alkyl group, or a C1 to C6 alkoxy group.
  • Y c2 represents a halogen atom, a cyano group, C 1 ⁇ C 6 alkyl group, C 1 ⁇ C 6 alkoxy group, a phenyl group which may be substituted
  • n c represents an integer of 0 to 4
  • m c represents an integer of 0 to 5.
  • DD The compound represented by general formula (DD) is as follows.
  • R d1 represents an optionally substituted phenyl group or an optionally substituted heterocyclyl group
  • R d2 and R d3 each independently represent a hydrogen atom or a C1-C6 alkyl group.
  • R d4 and R d5 each independently represents a halogen atom, a C1 to C6 alkyl group or a C1 to C6 haloalkyl group
  • R d6 represents a C1 to C6 haloalkyl group
  • Y d represents a halogen atom or a cyano group the stands
  • n d represents an integer of 1-4. When n d is 2 to 4, Y d may be the same or different.
  • the compound represented by general formula (EE) is as follows.
  • R e1 , R e2 , R e3 , and R e4 each independently represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or an optionally substituted phenyl.
  • group, Y e1, Y e2 each independently represents a halogen atom, C1 ⁇ C6 alkyl group, a C1 ⁇ C6 alkoxy group
  • n e represents an integer of 0 to 5
  • an integer of m e is 0-4 To express.
  • Y e1 When n e is 2 to 5, Y e1 may be the same or different, and when m e is 2 to 4, Y e2 may be the same or different.
  • Some of the compounds listed above can take stereoisomers, but these isomers are also included in the present invention.
  • the mixing ratio of the compound of the present invention and other insecticides and / or fungicides in the mixture of the compound of the present invention and other insecticides and / or fungicides is not particularly limited.
  • the compound of the present invention: other insecticides Agent and / or fungicide is 0.01: 100 to 100: 0.01, or 0.1: 100 to 100: 0.1, or 1: 100 to 100: 1, or 1:10 to 10: 1. Or 1: 1 (both in terms of weight).
  • Chloroacetylacetone (15.8 g, 118 mmol) was added to an ethanol solution (50 mL) of thionicotinamide (6.50 g, 47.0 mmol), and the mixture was stirred for 8 hours under reflux. After cooling, the formed precipitate was filtered off with suction, washed with ethanol and ethyl acetate and dried under reduced pressure. The obtained solid was gradually added to an aqueous potassium carbonate solution and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was filtered. The solvent was distilled off under reduced pressure to obtain the desired product (8.42 g) in a yield of 82%.
  • the obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter.
  • N, N-dimethylformamide dimethylacetal (3.45 g, 29.0 mmol) was added to thionicotinamide (2.00 g, 14.5 mmol), and the mixture was stirred at room temperature for 2 hours.
  • ethanol (20 mL) and bromoacetone (2.97 g, 21.7 mmol) were added, and the mixture was stirred at room temperature for 4 hours.
  • the produced solid was filtered, an aqueous potassium carbonate solution was added to the obtained mother liquor, and extraction was performed with ethyl acetate.
  • the obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter.
  • Step 2 1- (5- (pyridin-3-yl) thiazol-2-yl) ethanone O-methyl oxime compound (compound number: C-003)
  • O-methylhydroxylamine hydrochloride (1.23 g, 14) was added to a solution of 1- (5- (pyridin-3-yl) thiazol-2-yl) ethanone (0.20 g, 0.98 mmol) in ethanol (5 mL). 0.5 mmol) was added and stirred at reflux for 3 hours. Water was added to the reaction solution, and ethanol was distilled off under reduced pressure. A potassium carbonate aqueous solution was added, and extraction was performed with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter.
  • the target compound (0.35 g) was obtained with a yield of 80%.
  • Step 3 3- (4- (Ethylsulfonylmethyl) -5- (1- (methoxyimino) ethyl) thiazol-2-yl) pyridine 1-oxide compound (Compound number: A-073)
  • a magnesium bromide diethyl ether complex (0 mL) was added to a tetrahydrofuran solution (5 mL) of 1- (4-methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone oxime (0.20 g, 0.86 mmol). .29 g, 1.1 mmol) and ethyl isocyanate (79 ⁇ L, 1.1 mmol) were added, and the mixture was stirred at 60 ° C. for 3 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, and the mixture was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine.
  • the obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter.
  • the solvent was distilled off under reduced pressure, and purification was performed by silica gel chromatography (ethyl acetate) to obtain the target compound (0.14 g) in a yield of 53%.
  • Triethylamine (166 ⁇ L, 1.29) was added to a dichloromethane solution (5 mL) of 1- (4-methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone oxime (0.20 g, 0.86 mmol). mmol) and acetyl chloride (92 ⁇ L, 1.3 mmol) were added, and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, and the mixture was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter.
  • the obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter.
  • the solvent was distilled off under reduced pressure, and the resulting solid was washed with diisopropyl ether to obtain the desired product (0.20 g) in a yield of 78%.
  • the obtained organic layer was filtered through Celite and dried over magnesium sulfate, and then magnesium sulfate was removed with a filter.
  • Lithium hydroxide monohydrate (5.79 g) was added to a methanol solution (200 mL) of ethyl 1- (pyridin-3-yl) -1H-pyrazole-4-carboxylate (5.00 g, 23.0 mmol). 138 mmol) in water (20 mL) was added and stirred at room temperature for 5 hours. Methanol was distilled off under reduced pressure, pH was adjusted to 7 with concentrated hydrochloric acid, 5 mL of water was distilled off under reduced pressure, and the target compound (3.08 g) was obtained in a yield of 71% by filter filtration.
  • Step 4 1- (1- (Pyridin-3-yl) -1H-pyrazol-4-yl) ethanone
  • Step 5 1- (1- (Pyridin-3-yl) -1H-pyrazol-4-yl) ethanone oxime
  • Step 6 1- (1- (Pyridin-3-yl) -1H-pyrazol-4-yl) ethanone O-pyrimidin-2-yl oxime (compound number: C-009)
  • Tables 5 to 8 below show the compound numbers and details of the compounds of the present invention, including the compounds synthesized in this example.
  • (Formulation example 2) Uniformly stir 10 parts of the compound of the present invention represented by the general formula (I), 2 parts of sodium lauryl sulfate, 2 parts of dialkylsulfosuccinate, 1 part of sodium salt of ⁇ -naphthalenesulfonic acid formalin condensate and 85 parts of diatomaceous earth. A wettable powder was obtained by mixing.
  • the preparation When using the preparation obtained above, the preparation is diluted 1 to 10,000 times with water or sprayed directly without dilution.
  • Test Example 1 Insecticidal test against Japanese brown planthopper (Laodelfax striatellus)- 12.5 ml of 2% acetone aqueous solution prepared with 100 ppm of the test compound (the compound of the present invention) is placed in an Erlenmeyer flask, and the roots of rice seedlings are immersed. Furthermore, 2.5 ml of an acetone solution prepared with a test compound of 1000 ppm was sprayed on the leaves of rice seedlings and air-dried. Then, a transparent plastic tube was placed on the flask, and 10 3rd- and 4th-year-old larvae were placed inside the tube. Covered with a sponge plug. It left still in a 25 degreeC thermostat, and the number of live and dead insects was investigated 6 days afterward. No regime.
  • compound numbers A-003, A-005, A-016, A-021, A-030, A-049, A-054, A-055, A-057, A-064, A-065 , A-066, A-069, A-081, B-004, C-001, C-003, and C-007 showed a death rate of 70% or more.
  • Test Example 2 Insecticidal test (spraying test) against peach aphid (Myzu persicae)- 2.5 ml of 20% acetone aqueous solution prepared with 1000 ppm of the test compound was sprayed on the leaves of Japanese radish seedlings infested with the first instar larvae. After air drying, it was left still in a constant temperature room at 25 ° C., and the number of live and dead insects was examined after 5 days. No regime.
  • Test Example 3 -Insecticide test (Penetration transferability test) against peach aphid (Myzu persicae)- 15-20 ml of a 2% acetone aqueous solution prepared with 100 ppm of the test compound was placed in a tube bottle, and the roots of Japanese radish seedlings parasitized with the first instar larvae of the green peach were immersed. After leaving still in a constant temperature room at 25 ° C., the number of live and dead insects was examined after 5 days. No regime.
  • Test Example 5 -Insecticidal test against Spodoptera litura- Cabbage leaf pieces were immersed in a chemical solution prepared with a predetermined concentration of the test compound for 30 seconds and air-dried, and then placed in a 7 cm polyethylene cup with filter paper spread, and 5 second-instar larvae of the Japanese pearl moth were released. It left still in a 25 degreeC thermostat, and the number of live and dead insects was investigated 6 days afterward. No regime.
  • test compounds (Compound Nos. A-016, B-003, C-001, C-006) showed a death rate of 70% or more at a concentration of 1000 ppm.
  • Test Example 6 Insecticidal test against blue moth (Plutella xylostella)- Cabbage leaf pieces were immersed in a chemical solution prepared with a predetermined concentration of the test compound for 30 seconds and air-dried, and then placed in a 7 cm polyethylene cup with filter paper and five third-instar larvae were released. It left still in a 25 degreeC thermostat, and the number of live and dead insects was investigated 6 days afterward. No regime.
  • the compound Nos. A-016, A-041, A-042, A-044, A-062, B-003, and C-006 showed a death rate of 70% or more at a concentration of 1000 ppm. .
  • Test Example 7 -Insecticidal test against houseflies (Musca domestica)- 1 ml of an acetone solution prepared with a test compound at a predetermined concentration was dropped on a petri dish having a diameter of 9 cm and air-dried, and then 5 adult houseflies were released and capped. After leaving still in a constant temperature room at 25 ° C., the number of live and dead insects was examined one day later. No regime.
  • the compound Nos. A-006, A-016, A-034, and A-035 showed a death rate of 70% or more at a concentration of 1000 ppm.

Abstract

A compound which is represented by formula (I) (wherein G1 represents a carbon atom, a nitrogen atom or CH; R1 represents a hydrogen atom or the like; m represents an integer of 1-3; n represents 0 or 1; Hy represents a five-membered or six-membered aromatic ring represented by formula (B0) (wherein *2 represents the bonding position to G2); A1 represents a carbon atom or a nitrogen atom, A2 represents a carbon atom or a sulfur atom, A3 represents a carbon atom or a nitrogen atom, and A4 represents a carbon atom or a nitrogen atom, provided that A1 and A2 are not carbon atoms at the same time; p represents an integer of 0-2; q represents 0 or 1; R2 represents a hydrogen atom, a C1-C6 alkyl group or the like; Q represents an oxygen atom or NR5; R3 represents a hydrogen atom, a C1-C6 alkyl group or the like; and R4 represents a C1-C6 alkyl group, an optionally substituted hetero ring or the like); a pest control agent which contains the compound as an active ingredient; a method for producing the pest control agent; and a use of the pest control agent.

Description

有害生物防除剤として使用される複素環化合物又はその塩Heterocyclic compounds or salts thereof used as pest control agents
　本発明は、有害生物防除剤として使用される複素環化合物又はその塩に関するものである。 The present invention relates to a heterocyclic compound or a salt thereof used as a pest control agent.
　特許文献１～１７には、殺虫剤として本発明化合物と類似した化合物の記載が認められる。しかし、該化合物は、本発明化合物とは異なる化合物であることは明らかである。
　また、特許文献１８には、殺菌剤として本発明化合物と類似した化合物の記載が認められる。しかし、該化合物は、本発明化合物とは異なる化合物であることは明らかである。 In Patent Documents 1 to 17, description of compounds similar to the compound of the present invention as insecticides is recognized. However, it is clear that the compound is different from the compound of the present invention.
Patent Document 18 recognizes a compound similar to the compound of the present invention as a fungicide. However, it is clear that the compound is different from the compound of the present invention.
国際公開第２００９／１４９８５８号パンフレットInternational Publication No. 2009/149858 Pamphlet 国際公開第２０１０／００６７１３号パンフレットInternational Publication No. 2010/006713 Pamphlet 国際公開第２０１０／１２９４９７号パンフレットInternational Publication No. 2010/129497 Pamphlet 国際公開第２０１１／０４５２２４号パンフレットInternational Publication No. 2011/045224 Pamphlet 国際公開第２０１１／０４５２４０号パンフレットInternational Publication No. 2011/045240 Pamphlet 国際公開第２０１１／１２８３０４号パンフレットInternational Publication No. 2011/128304 Pamphlet 国際公開第２０１１／１３８２８５号パンフレットInternational Publication No. 2011/138285 Pamphlet 国際公開第２０１１／１３４９６４号パンフレットInternational Publication No. 2011-134964 Pamphlet 国際公開第２０１２／０００８９６号パンフレットInternational Publication No. 2012/000896 Pamphlet 国際公開第２０１２／００７５００号パンフレットInternational Publication No. 2012/007500 Pamphlet 国際公開第２０１２／０６１２８８号パンフレットInternational Publication No. 2012/061288 Pamphlet 国際公開第２０１２／０６１２９０号パンフレットInternational Publication No. 2012/061290 Pamphlet 国際公開第２０１２／１０２３８７号パンフレットInternational Publication No. 2012/102387 Pamphlet 国際公開第２０１２／１０８５１１号パンフレットInternational Publication No. 2012/108511 Pamphlet 国際公開第２０１２／１１６２４６号パンフレットInternational Publication No. 2012/116246 Pamphlet 国際公開第２０１２／１６８３６１号パンフレットInternational Publication No. 2012/168361 Pamphlet 国際公開第２０１３／０００９３１号パンフレットInternational Publication No. 2013/000931 Pamphlet 国際公開第１９９２／０１８４８７号パンフレットInternational Publication No. 1992/018487 Pamphlet
　本発明の目的は、高い殺虫効果を有する有害生物防除剤に有効成分として含有され得る複素環化合物又はその塩を提供することにある。
　また、本発明の他の目的は、一般式（Ｉ）で表される複素環化合物又はその塩（以下、「本発明化合物」と称する場合がある）、該化合物の製造方法、該化合物を有効成分として含有する有害生物防除剤、及び該化合物と他の殺虫剤及び／又は殺菌剤を組み合わせて使用する病害虫の防除方法を提供することにある。
　なお、他の殺虫剤及び殺菌剤とは、本発明化合物とは異なるものを示す。 The objective of this invention is providing the heterocyclic compound or its salt which can be contained as an active ingredient in the pest control agent which has a high insecticidal effect.
Another object of the present invention is to provide a heterocyclic compound represented by the general formula (I) or a salt thereof (hereinafter sometimes referred to as “the compound of the present invention”), a method for producing the compound, and effective use of the compound. An object of the present invention is to provide a pest control agent contained as a component and a method for controlling pests using the compound in combination with other insecticides and / or fungicides.
Other insecticides and fungicides are different from the compounds of the present invention.
　本発明者らは、上記課題を解決するために鋭意研究を重ねた結果、本発明化合物は文献未記載の新規な化合物であり、顕著に優れた殺虫効果を有することから、有害生物防除剤としての新規な用途を見出した。その結果、本発明を完成するに至ったものである。
　すなわち、本発明は下記の実施形態を含む。 As a result of intensive studies in order to solve the above problems, the present inventors are a novel compound not described in the literature, and have a remarkably excellent insecticidal effect. Has found a new use. As a result, the present invention has been completed.
That is, the present invention includes the following embodiments.
［１］下記一般式（Ｉ） [1] The following general formula (I)
Figure JPOXMLDOC01-appb-C000007
Figure JPOXMLDOC01-appb-C000007
｛一般式（Ｉ）中、
　Ｇ１は、窒素原子、炭素原子、又はＣＨを表す。
　Ｒ１は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１－Ｃ６アルキル基、Ｃ２－Ｃ６アルケニル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、又はＣ１－Ｃ６ハロアルキルスルホニル基を表す。
　ｍは、１～３の整数を表し、ｍが２以上の整数を表すとき、各々のＲ１はお互いに同一であっても、相異なってもよい。
　ｎは、０又は１を表す。
　Ｈｙは、下記一般式（Ｂ０） {In general formula (I),
G 1 represents a nitrogen atom, a carbon atom, or CH.
R 1 is a hydrogen atom, halogen atom, cyano group, nitro group, C1-C6 alkyl group, C2-C6 alkenyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 An alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylsulfonyl group is represented.
m represents an integer of 1 to 3, and when m represents an integer of 2 or more, each R 1 may be the same as or different from each other.
n represents 0 or 1.
Hy represents the following general formula (B0)
Figure JPOXMLDOC01-appb-C000008
Figure JPOXMLDOC01-appb-C000008
で表される５員環又は６員環の芳香族環を表す（＊２はＧ２への結合位置を表す）。
　ここで、Ａ１は、炭素原子又は窒素原子を表す。
　Ａ２は、炭素原子又は硫黄原子を表す。
　Ａ３は、炭素原子又は窒素原子を表す。
　Ａ４は、炭素原子又は窒素原子を表す。
　ただし、Ａ１とＡ２が共に炭素原子であることはない。
　ｐは、０～２の整数を表す。
　ｑは、０又は１を表す。
　Ｒ２は、水素原子、ハロゲン原子、Ｃ１－Ｃ６アルキル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、又は、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルホニル基、ヒドロキシアミノ基、アシルヒドラジニル基、若しくは置換されていてもよいイミダゾイル基で置換されたＣ１－Ｃ６アルキル基を表す。
　Ｇ２は、下記一般式（Ｉ－Ｇ２） Represents a 5-membered or 6-membered aromatic ring represented by the formula (* 2 represents a bonding position to G2).
Here, A 1 represents a carbon atom or a nitrogen atom.
A 2 represents a carbon atom or a sulfur atom.
A 3 represents a carbon atom or a nitrogen atom.
A 4 represents a carbon atom or a nitrogen atom.
However, A 1 and A 2 are not both carbon atoms.
p represents an integer of 0 to 2.
q represents 0 or 1;
R 2 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1- C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, or C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 It represents a C1-C6 alkyl group substituted with an alkylsulfonyl group, a hydroxyamino group, an acyl hydrazinyl group, or an optionally substituted imidazolyl group.
G 2 represents the following general formula (IG 2 )
Figure JPOXMLDOC01-appb-C000009
Figure JPOXMLDOC01-appb-C000009
で表される置換基である（＊１はＨｙへの結合位置を表す）。
　ここで、Ｑは、酸素原子、又はＮＲ５を表す。
　Ｒ５は、水素原子、Ｃ１－Ｃ６アルキル基、Ｃ３－Ｃ６シクロアルキル基、Ｃ２－Ｃ６アルケニル基、Ｃ２－Ｃ６アルキニル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、Ｃ１－Ｃ６アルコキシカルボニル基、Ｃ１－Ｃ６アルキルカルボニル基、Ｃ１－Ｃ６アルキルアミノカルボニル基、又はジ（Ｃ１－Ｃ６アルキル）アミノカルボニル基を表す。 (* 1 represents the bonding position to Hy).
Here, Q represents an oxygen atom or NR 5 .
R 5 is a hydrogen atom, C1-C6 alkyl group, C3-C6 cycloalkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 haloalkyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl Group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkylaminocarbonyl group, or a di (C1-C6 alkyl) aminocarbonyl group.
　Ｒ３は、水素原子、Ｃ１－Ｃ６アルキル基、Ｃ３－Ｃ６シクロアルキル基、Ｃ２－Ｃ６アルケニル基、Ｃ２－Ｃ６アルキニル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、Ｃ1－Ｃ６アルコキシカルボニル基、ホルミル基、Ｃ1－Ｃ６アルキルカルボニル基、Ｃ１－Ｃ６アルキルアミノカルボニル基又はジ（Ｃ１－Ｃ６アルキル）アミノカルボニル基、又はＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６アルキル基を表す。
　Ｒ２とＲ３は互いに結合して５員環又は６員環を形成していてもよい。 R 3 is a hydrogen atom, C1-C6 alkyl group, C3-C6 cycloalkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkoxycarbonyl group, formyl Group, C1-C6 alkylcarbonyl group, C1-C6 alkylaminocarbonyl group or di (C1-C6 alkyl) aminocarbonyl group, or C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1- A C6 alkylsulfinyl group, 1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, or a C1-C6 alkyl group substituted with a C1-C6 haloalkylsulfonyl group.
R 2 and R 3 may be bonded to each other to form a 5-membered ring or a 6-membered ring.
　Ｒ４は、Ｃ１－Ｃ６アルキル基、Ｃ３－Ｃ６シクロアルキル基、Ｃ２－Ｃ６アルケニル基、Ｃ２－Ｃ６アルキニル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、Ｃ１－Ｃ６アルコキシカルボニル基、Ｃ１－Ｃ６ハロアルコキシカルボニル基、Ｃ１－Ｃ６アルキルカルボニル基、Ｃ１－Ｃ６ハロアルキルカルボニル基、Ｃ１－Ｃ６アルキルアミノカルボニル基、置換されていてもよいフェニルアミノカルボニル基、Ｃ１－Ｃ６ハロアルキルアミノカルボニル基、ジ（Ｃ１－Ｃ６アルキル）アミノカルボニル基、（Ｃ１－Ｃ６アルキル）（Ｃ１－Ｃ６ハロアルキル）アミノカルボニル基、ジ（Ｃ１－Ｃ６ハロアルキル）アミノカルボニル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、置換されていてもよいベンゾイル基、置換されていてもよいＣ１－Ｃ６アルキル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６アルキル基）、置換されていてもよいＣ１－Ｃ６ハロアルキル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６ハロアルキル基）、置換されていてもよいＣ１－Ｃ６アルキルカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６アルキルカルボニル基）、置換されていてもよいＣ１－Ｃ６ハロアルキルカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６ハロアルキルカルボニル基）、置換されていてもよいＣ１－Ｃ６アルコキシカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６アルコキシカルボニル基）、置換されていてもよいＣ１－Ｃ６ハロアルコキシカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６ハロアルコキシカルボニル基）、置換されていてもよいＣ１－Ｃ６アルキルアミノカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６アルキルアミノカルボニル基）、置換されていてもよいＣ１－Ｃ６ハロアルキルアミノカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６ハロアルキルアミノカルボニル基）を表すか、または、Ｒ４は、置換されていてもよいヘテロシクリル基、置換されていてもよいフラニル基、置換されていてもよいチエニル基、置換されていてもよいピロリル基、置換されていてもよいピラゾリル基、置換されていてもよいイミダゾリル基、置換されていてもよい１，２，３－トリアゾリル基、置換されていてもよい１，２，４－トリアゾリル基、置換されていてもよいオキサゾリル基、置換されていてもよいイソオキサゾリル基、置換されていてもよいチアゾリル基、置換されていてもよいイソチアゾリル基、置換されていてもよい１，２，３－オキサジアゾリル基、置換されていてもよい１，２，４－オキサジアゾリル基、置換されていてもよい１，３，４－オキサジアゾリル基、置換されていてもよい１，２，５－オキサジアゾリル基、置換されていてもよい１，２，３－チアジアゾリル基、置換されていてもよい１，２，４－チアジアゾリル基、置換されていてもよい１，３，４－チアジアゾリル、置換されていてもよい１，２，５－チアジアゾリル基、置換されていてもよいピリジル基、置換されていてもよいピリミジニル基、置換されていてもよいピリダジニル基、置換されていてもよいピラジニル基、置換されていてもよい１，２，３－トリアジニル基、置換されていてもよい１，２，４－トリアジニル基、置換されていてもよい１，３，５－トリアジニル基、置換されていてもよいベンゾフリル基、置換されていてもよいベンゾイソフリル基、置換されていてもよいベンゾチエニル基、置換されていてもよいベンゾイソチエニル基、置換されていてもよいインドリル基、置換されていてもよいイソインドリル基、置換されていてもよいインダゾリル基、置換されていてもよいベンゾチアゾリル基、置換されていてもよいベンゾイソチアゾリル基、置換されていてもよいベンゾオキサゾリル基、置換されていてもよいベンゾイソオキサゾリル基、置換されていてもよいベンゾイミダゾリル基、置換されていてもよい２，１，３－ベンゾオキサジアゾール基、置換されていてもよいキノリニル基、置換されていてもよいイソキノリニル基、置換されていてもよいシンノリニル基、置換されていてもよいフタラジニル基、置換されていてもよいキナゾリニル基、置換されていてもよいキノキサリニル基、置換されていてもよいナフチリジニル基、置換されていてもよいベンゾトリアジニル基、置換されていてもよいプリニル基、置換されていてもよいプテリジニル基、置換されていてもよいインドリジニル基、又はシアノ基、ニトロ基、ハロアルコキシ基、若しくはヘテロシクリル基で置換されているアリール基を表す。
　ただし、Ａ１が窒素原子かつＡ２が硫黄原子かつＱが酸素原子かつｎが０の場合、Ｒ４は置換されていてもよいヘテロシクリル基、置換されていてもよいフラニル基、置換されていてもよいチエニル基、置換されていてもよいピロリル基、置換されていてもよいピラゾリル基、置換されていてもよいイミダゾリル基、置換されていてもよい１，２，３－トリアゾリル基、置換されていてもよい１，２，４－トリアゾリル基、置換されていてもよいオキサゾリル基、置換されていてもよいイソオキサゾリル基、置換されていてもよいチアゾリル基、置換されていてもよいイソチアゾリル基、置換されていてもよい１，２，３－オキサジアゾリル基、置換されていてもよい１，２，４－オキサジアゾリル基、置換されていてもよい１，３，４－オキサジアゾリル基、置換されていてもよい１，２，５－オキサジアゾリル基、置換されていてもよい１，２，３－チアジアゾリル基、置換されていてもよい１，２，４－チアジアゾリル基、置換されていてもよい１，３，４－チアジアゾリル、置換されていてもよい１，２，５－チアジアゾリル基、置換されていてもよいピリジル基、置換されていてもよいピリミジニル基、置換されていてもよいピリダジニル基、置換されていてもよいピラジニル基、置換されていてもよい１，２，３－トリアジニル基、置換されていてもよい１，２，４－トリアジニル基、置換されていてもよい１，３，５－トリアジニル基、置換されていてもよいベンゾフリル基、置換されていてもよいベンゾイソフリル基、置換されていてもよいベンゾチエニル基、置換されていてもよいベンゾイソチエニル基、置換されていてもよいインドリル基、置換されていてもよいイソインドリル基、置換されていてもよいインダゾリル基、置換されていてもよいベンゾチアゾリル基、置換されていてもよいベンゾイソチアゾリル基、置換されていてもよいベンゾオキサゾリル基、置換されていてもよいベンゾイソオキサゾリル基、置換されていてもよいベンゾイミダゾリル基、置換されていてもよい２，１，３－ベンゾオキサジアゾール基、置換されていてもよいキノリニル基、置換されていてもよいイソキノリニル基、置換されていてもよいシンノリニル基、置換されていてもよいフタラジニル基、置換されていてもよいキナゾリニル基、置換されていてもよいキノキサリニル基、置換されていてもよいナフチリジニル基、置換されていてもよいベンゾトリアジニル基、置換されていてもよいプリニル基、置換されていてもよいプテリジニル基及びインドリジニル基、又はシアノ基、ニトロ基、ハロアルコキシ基、若しくはヘテロシクリル基で置換されているアリール基であることはない。
　また、Ａ１が窒素原子かつＡ２が硫黄原子かつＡ３が炭素原子かつＲ２がメチル基かつＱがＮＲ５かつＲ５が水素原子の場合、Ｒ４はメトキシカルボニル基であることはない。｝
で表される、複素環化合物又はその塩。 R 4 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1 -C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkylaminocarbonyl group, optionally substituted phenylaminocarbonyl group, C1-C6 Haloalkylaminocarbonyl group, di (C1-C6 alkyl) aminocarbonyl group, (C1-C6 alkyl) (C1-C6 haloalkyl) aminocarbonyl group, di (C1-C6 haloalkyl) aminocarbonyl group, C1-C6 alkoxy group, C1 -C6 halo Alkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, optionally substituted benzoyl group, optionally substituted C1-C6 alkyl group (Preferably C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, Or a C1-C6 alkyl group substituted with a C1-C6 haloalkylsulfonyl group), an optionally substituted C1-C6 haloalkyl group (preferably a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group) C1-C6 Al Rusulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, or C1-C6 haloalkyl group substituted with C1-C6 haloalkylsulfonyl group), optionally substituted C1 -C6 alkylcarbonyl group (preferably C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1- A C6-haloalkylsulfinyl group or a C1-C6 alkylcarbonyl group substituted with a C1-C6 haloalkylsulfonyl group), an optionally substituted C1-C6 haloalkylcarbonyl group (preferably a C1-C6 alkoxy group, a C1-C6 group) C1-C6 substituted with an alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylsulfonyl group C6-haloalkylcarbonyl group), optionally substituted C1-C6 alkoxycarbonyl group (preferably C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6) An alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 alkoxycarbonyl group substituted with a C1-C6 haloalkylsulfonyl group), an optionally substituted C1-C6 halo Alkoxycarbonyl group (preferably C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkyl group) A sulfinyl group, or a C1-C6 haloalkoxycarbonyl group substituted with a C1-C6 haloalkylsulfonyl group), an optionally substituted C1-C6 alkylaminocarbonyl group (preferably a C1-C6 alkoxy group, a C1-C6 haloalkoxy group) A C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylsulfonyl group. C1-C6 alkylaminocarbonyl group), an optionally substituted C1-C6 haloalkylaminocarbonyl group (preferably a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkyl group) A sulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylaminocarbonyl group substituted with a C1-C6 haloalkylsulfonyl group), or R 4 is an optionally substituted heterocyclyl group, an optionally substituted furanyl group, an optionally substituted thienyl group, an optionally substituted pyrrolyl group, an optionally substituted pyrazolyl group, a substituted Optionally substituted imidazolyl group, substituted 1,2,3-triazolyl group which may be substituted, 1,2,4-triazolyl group which may be substituted, oxazolyl group which may be substituted, isoxazolyl group which may be substituted, A good thiazolyl group, an optionally substituted isothiazolyl group, an optionally substituted 1,2,3-oxadiazolyl group, an optionally substituted 1,2,4-oxadiazolyl group, an optionally substituted 1 , 3,4-oxadiazolyl group, optionally substituted 1,2,5-oxadiazolyl group, optionally substituted 1,2,3-thiadiazolyl group, optionally substituted 1,2,4- Thiadiazolyl group, optionally substituted 1,3,4-thiadiazolyl, optionally substituted 1,2,5-thiadiazolyl group, optionally substituted pyria Group, an optionally substituted pyrimidinyl group, an optionally substituted pyridazinyl group, an optionally substituted pyrazinyl group, an optionally substituted 1,2,3-triazinyl group, an optionally substituted 1,2,4-triazinyl group, 1,3,5-triazinyl group which may be substituted, benzofuryl group which may be substituted, benzoisofuryl group which may be substituted, Good benzothienyl group, optionally substituted benzisothienyl group, optionally substituted indolyl group, optionally substituted isoindolyl group, optionally substituted indazolyl group, optionally substituted benzothiazolyl Group, optionally substituted benzoisothiazolyl group, optionally substituted benzoxazolyl group, optionally substituted Benzoisoxazolyl group, optionally substituted benzimidazolyl group, optionally substituted 2,1,3-benzooxadiazole group, optionally substituted quinolinyl group, optionally substituted isoquinolinyl Group, an optionally substituted cinnolinyl group, an optionally substituted phthalazinyl group, an optionally substituted quinazolinyl group, an optionally substituted quinoxalinyl group, an optionally substituted naphthyridinyl group, a substituted An optionally substituted benzotriazinyl group, an optionally substituted prynyl group, an optionally substituted pteridinyl group, an optionally substituted indolizinyl group, or a cyano group, nitro group, haloalkoxy group, or heterocyclyl group Represents an aryl group substituted by.
However, when A 1 is a nitrogen atom, A 2 is a sulfur atom, Q is an oxygen atom, and n is 0, R 4 is an optionally substituted heterocyclyl group, an optionally substituted furanyl group, An optionally substituted thienyl group, an optionally substituted pyrrolyl group, an optionally substituted pyrazolyl group, an optionally substituted imidazolyl group, an optionally substituted 1,2,3-triazolyl group, a substituted 1,2,4-triazolyl group which may be substituted, oxazolyl group which may be substituted, isoxazolyl group which may be substituted, thiazolyl group which may be substituted, isothiazolyl group which may be substituted, substituted 1,2,3-oxadiazolyl group which may be substituted, 1,2,4-oxadiazolyl group which may be substituted, 1,3,4-optionally substituted Oxadiazolyl group, optionally substituted 1,2,5-oxadiazolyl group, optionally substituted 1,2,3-thiadiazolyl group, optionally substituted 1,2,4-thiadiazolyl group, substituted 1,3,4-thiadiazolyl which may be substituted, 1,2,5-thiadiazolyl which may be substituted, pyridyl which may be substituted, pyrimidinyl which may be substituted, A good pyridazinyl group, an optionally substituted pyrazinyl group, an optionally substituted 1,2,3-triazinyl group, an optionally substituted 1,2,4-triazinyl group, an optionally substituted 1 , 3,5-triazinyl group, optionally substituted benzofuryl group, optionally substituted benzoisofuryl group, optionally substituted benzothienyl group, Benzoisothienyl group which may be substituted, indolyl group which may be substituted, isoindolyl group which may be substituted, indazolyl group which may be substituted, benzothiazolyl group which may be substituted, substituted Optionally substituted benzoisothiazolyl group, optionally substituted benzoxazolyl group, optionally substituted benzisoxazolyl group, optionally substituted benzimidazolyl group, optionally substituted 2 1,3-Benzoxadiazole group, optionally substituted quinolinyl group, optionally substituted isoquinolinyl group, optionally substituted cinnolinyl group, optionally substituted phthalazinyl group, substituted Quinazolinyl group which may be substituted, quinoxalinyl group which may be substituted, naphthyl which may be substituted A dinyl group, an optionally substituted benzotriazinyl group, an optionally substituted purinyl group, an optionally substituted pteridinyl group and indolizinyl group, or a cyano group, a nitro group, a haloalkoxy group, or a heterocyclyl group It is not an aryl group substituted with.
When A 1 is a nitrogen atom, A 2 is a sulfur atom, A 3 is a carbon atom, R 2 is a methyl group, Q is NR 5 and R 5 is a hydrogen atom, R 4 is not a methoxycarbonyl group. . }
The heterocyclic compound or its salt represented by these.
［２］Ｈｙが、下記式（Ｂ１）から式（Ｂ１１）のいずれかを表す、
Figure JPOXMLDOC01-appb-C000010
 [2] Hy represents any one of the following formulas (B 1 ) to (B 11 ):
Figure JPOXMLDOC01-appb-C000010
　｛上記式（Ｂ１）から式（Ｂ１１）中、
　Ｒ２は、水素原子、ハロゲン原子、Ｃ１－Ｃ６アルキル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、又は、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルホニル基、ヒドロキシアミノ基、アシルヒドラジニル基、若しくは置換されていてもよいイミダゾイル基で置換されたＣ１－Ｃ６アルキル基を表す。
　＊２はＧ２への結合位置を表す。｝
　［１］に記載の複素環化合物又はその塩。 {From the above formula (B 1 ) to formula (B 11 )
R 2 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1- C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, or C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 It represents a C1-C6 alkyl group substituted with an alkylsulfonyl group, a hydroxyamino group, an acyl hydrazinyl group, or an optionally substituted imidazolyl group.
* 2 represents a bonding position to G 2. }
The heterocyclic compound or salt thereof according to [1].
［３］ＱがＮＲ５を表す、［２］に記載の複素環化合物又はその塩。 [3] The heterocyclic compound or a salt thereof according to [2], wherein Q represents NR 5 .
［４］ＱがＮＲ５を表し、Ｈｙが、下記式（Ｂ１）、（Ｂ２）、（Ｂ４）、（Ｂ５）、（Ｂ６）、（Ｂ７）、（Ｂ８）又は（Ｂ９）を表す
Figure JPOXMLDOC01-appb-C000011
 [4] Q represents NR 5 and Hy represents the following formulas (B 1 ), (B 2 ), (B 4 ), (B 5 ), (B 6 ), (B 7 ), (B 8 ) or Represents (B 9 )
Figure JPOXMLDOC01-appb-C000011
　｛上記式（Ｂ１）、（Ｂ２）、（Ｂ４）、（Ｂ５）、（Ｂ６）、（Ｂ７）、（Ｂ８）及び（Ｂ９）中
　Ｒ２は、前記と同様の意味を表し、＊２はＧ２への結合位置を表す。｝
　［３］に記載の複素環化合物又はその塩。 {In the above formulas (B 1 ), (B 2 ), (B 4 ), (B 5 ), (B 6 ), (B 7 ), (B 8 ) and (B 9 ), R 2 is the same as above the meaning of, * 2 denotes the point of attachment to G 2. }
The heterocyclic compound or salt thereof according to [3].
［５］Ｑが酸素原子を表す、［２］に記載の複素環化合物又はその塩。 [5] The heterocyclic compound or a salt thereof according to [2], wherein Q represents an oxygen atom.
［６］Ｑが酸素原子を表し、Ｈｙが、下記式（Ｂ１）、（Ｂ２）、（Ｂ４）、（Ｂ５）、（Ｂ６）、（Ｂ７）、（Ｂ８）又は（Ｂ９）を表す
Figure JPOXMLDOC01-appb-C000012
 [6] Q represents an oxygen atom, and Hy represents the following formula (B 1 ), (B 2 ), (B 4 ), (B 5 ), (B 6 ), (B 7 ), (B 8 ) or Represents (B 9 )
Figure JPOXMLDOC01-appb-C000012
　｛上記式（Ｂ１）、（Ｂ２）、（Ｂ４）、（Ｂ５）、（Ｂ６）、（Ｂ７）、（Ｂ８）及び（Ｂ９）中
　Ｒ２は、前記と同様の意味を表し、＊２はＧ２への結合位置を表す。｝
　［５］に記載の複素環化合物又はその塩。 {In the above formulas (B 1 ), (B 2 ), (B 4 ), (B 5 ), (B 6 ), (B 7 ), (B 8 ) and (B 9 ), R 2 is the same as above the meaning of, * 2 denotes the point of attachment to G 2. }
The heterocyclic compound or a salt thereof according to [5].
［７］［１］から［６］のいずれか１項に記載の複素環化合物又はその塩と、不活性担体又は補助剤と、を含む組成物。 [7] A composition comprising the heterocyclic compound or a salt thereof according to any one of [1] to [6], and an inert carrier or adjuvant.
［８］［１］から［６］のいずれか１項に記載の複素環化合物又はその塩を有効成分として含有する有害生物防除剤。 [8] A pest control agent comprising the heterocyclic compound or a salt thereof according to any one of [1] to [6] as an active ingredient.
［９］［１］から［６］のいずれか１項に記載の複素環化合物又はその塩を有効成分として含有する農園芸用有害生物防除剤。 [9] An agricultural and horticultural pest control agent comprising the heterocyclic compound or a salt thereof according to any one of [1] to [6] as an active ingredient.
［１０］［１］から［６］のいずれか１項に記載の複素環化合物又はその塩の有効量を含む薬剤を、有用作物又は土壌に処理することを含む前記薬剤の使用方法。 [10] A method of using the drug, comprising treating a drug containing an effective amount of the heterocyclic compound or the salt thereof according to any one of [1] to [6] with a useful crop or soil.
［１１］［１］から［６］のいずれか１項に記載の複素環化合物又はその塩と、前記複素環化合物又はその塩とは異なる、他の殺虫剤及び／又は殺菌剤のうち１種以上と、を含む混合物。
［１２］［１］から［６］のいずれか１項に記載の複素環化合物又はその塩の有効量を含む薬剤を、有用作物又は土壌に処理することを含む、有害生物防除方法。
  [11] The heterocyclic compound or salt thereof according to any one of [1] to [6] and one of other insecticides and / or fungicides different from the heterocyclic compound or salt thereof A mixture comprising the above.
[12] A method for controlling pests, comprising treating a useful crop or soil with a drug containing an effective amount of the heterocyclic compound or salt thereof according to any one of [1] to [6].
　本発明化合物は、有害生物防除剤に含有させた場合に優れた防除効果を実現する。
　また、他の殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、除草剤、植物成長調節剤、生物農薬などと組み合わせて使用することによっても優れた防除効果を示すものである。 The compound of the present invention realizes an excellent control effect when contained in a pest control agent.
It also exhibits excellent control effect when used in combination with other insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, biological pesticides and the like.
　さらに、本発明化合物は、有害生物防除剤に含有させた場合に優れた防除効果を実現する。 Furthermore, the compound of the present invention realizes an excellent control effect when contained in a pest control agent.
　本発明の複素環化合物又はその塩は、下記一般式（Ｉ）で表される複素環化合物又はその塩（本発明化合物）である。
　本発明化合物を有効成分として含有する有害生物防除剤は、高い殺虫効果を有することとなる。 The heterocyclic compound or a salt thereof of the present invention is a heterocyclic compound represented by the following general formula (I) or a salt thereof (the present compound).
The pest control agent containing the compound of the present invention as an active ingredient has a high insecticidal effect.
　本発明化合物は、下記一般式（Ｉ） The compound of the present invention has the following general formula (I)
Figure JPOXMLDOC01-appb-C000013
Figure JPOXMLDOC01-appb-C000013
｛一般式（Ｉ）中、
　Ｇ１は、窒素原子、炭素原子、又はＣＨを表す。
　Ｒ１は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１－Ｃ６アルキル基、Ｃ２－Ｃ６アルケニル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、又はＣ１－Ｃ６ハロアルキルスルホニル基を表す。
　ｍは、１～３の整数を示し、ｍが２以上の整数を表すとき、各々のＲ１はお互いに同一であっても、相異なってもよい。
　ｎは、０又は１を表す。 {In general formula (I),
G 1 represents a nitrogen atom, a carbon atom, or CH.
R 1 is a hydrogen atom, halogen atom, cyano group, nitro group, C1-C6 alkyl group, C2-C6 alkenyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 An alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylsulfonyl group is represented.
m represents an integer of 1 to 3, and when m represents an integer of 2 or more, each R 1 may be the same as or different from each other.
n represents 0 or 1.
　Ｈｙは、下記一般式（Ｂ０）
Figure JPOXMLDOC01-appb-C000014
 Hy represents the following general formula (B0)
Figure JPOXMLDOC01-appb-C000014
で表される５員環又は６員環の芳香族環を表す（＊２はＧ２への結合位置を表す。点線はＮ、Ｇ１を有する環への結合位置を表す。）。
　ここで、Ａ１は炭素原子又は窒素原子を表す。
　Ａ２は炭素原子又は硫黄原子を表す。
　Ａ３は炭素原子又は窒素原子を表す。
　Ａ４は炭素原子又は窒素原子を表す。
　ただし、Ａ１とＡ２が共に炭素原子であることはない。
　ｐは、０～２の整数を示す。
　ｑは０又は１を表す。 In 5-membered ring or an six-membered aromatic ring represented (in * 2. Dotted line shows the point of attachment to the G2 represents the point of attachment to the ring with N, a G 1.).
Here, A 1 represents a carbon atom or a nitrogen atom.
A 2 represents a carbon atom or a sulfur atom.
A 3 represents a carbon atom or a nitrogen atom.
A 4 represents a carbon atom or a nitrogen atom.
However, A 1 and A 2 are not both carbon atoms.
p represents an integer of 0-2.
q represents 0 or 1;
　Ｒ２は、水素原子、ハロゲン原子、Ｃ１－Ｃ６アルキル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、又は、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルホニル基、ヒドロキシアミノ基、アシルヒドラジニル基、若しくは置換されていてもよいイミダゾイル基で置換されたＣ１－Ｃ６アルキル基を表す。 R 2 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1- C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, or C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 It represents a C1-C6 alkyl group substituted with an alkylsulfonyl group, a hydroxyamino group, an acyl hydrazinyl group, or an optionally substituted imidazolyl group.
　Ｇ２は、下記一般式（Ｉ－Ｇ２） G 2 represents the following general formula (IG 2 )
Figure JPOXMLDOC01-appb-C000015
 
Figure JPOXMLDOC01-appb-C000015
 
　で表される置換基である（＊１はＨｙへの結合位置を表す）。
　ここで、Ｑは、酸素原子、又はＮＲ５を表す。
　Ｒ５は、水素原子、Ｃ１－Ｃ６アルキル基、Ｃ３－Ｃ６シクロアルキル基、Ｃ２－Ｃ６アルケニル基、Ｃ２－Ｃ６アルキニル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、Ｃ１－Ｃ６アルコキシカルボニル基、Ｃ１－Ｃ６アルキルカルボニル基、Ｃ１－Ｃ６アルキルアミノカルボニル基、又はジ（Ｃ１－Ｃ６アルキル）アミノカルボニル基を表す。 (* 1 represents the bonding position to Hy).
Here, Q represents an oxygen atom or NR 5 .
R 5 is a hydrogen atom, C1-C6 alkyl group, C3-C6 cycloalkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 haloalkyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl Group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkylaminocarbonyl group, or a di (C1-C6 alkyl) aminocarbonyl group.
　Ｒ３は、水素原子、Ｃ１－Ｃ６アルキル基、Ｃ３－Ｃ６シクロアルキル基、Ｃ２－Ｃ６アルケニル基、Ｃ２－Ｃ６アルキニル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、Ｃ１－Ｃ６アルコキシカルボニル基、ホルミル基、Ｃ１－Ｃ６アルキルカルボニル基、Ｃ１－Ｃ６アルキルアミノカルボニル基又はジ（Ｃ１－Ｃ６アルキル）アミノカルボニル基、又はＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６アルキル基を表す。
　Ｒ２とＲ３は互いに結合して５員環又は６員環を形成していてもよい。 R 3 is a hydrogen atom, C1-C6 alkyl group, C3-C6 cycloalkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkoxycarbonyl group, formyl Group, C1-C6 alkylcarbonyl group, C1-C6 alkylaminocarbonyl group or di (C1-C6 alkyl) aminocarbonyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1- C6 alkylsulfinyl group , A C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 alkyl group substituted with a C1-C6 haloalkylsulfonyl group.
R 2 and R 3 may be bonded to each other to form a 5-membered ring or a 6-membered ring.
　Ｒ４は、Ｃ１－Ｃ６アルキル基、Ｃ３－Ｃ６シクロアルキル基、Ｃ２－Ｃ６アルケニル基、Ｃ２－Ｃ６アルキニル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、Ｃ１－Ｃ６アルコキシカルボニル基、Ｃ１－Ｃ６ハロアルコキシカルボニル基、Ｃ１－Ｃ６アルキルカルボニル基、Ｃ１－Ｃ６ハロアルキルカルボニル基、Ｃ１－Ｃ６アルキルアミノカルボニル基、置換されていてもよいフェニルアミノカルボニル基、Ｃ１－Ｃ６ハロアルキルアミノカルボニル基、ジ（Ｃ１－Ｃ６アルキル）アミノカルボニル基、（Ｃ１－Ｃ６アルキル）（Ｃ１－Ｃ６ハロアルキル）アミノカルボニル基、ジ（Ｃ１－Ｃ６ハロアルキル）アミノカルボニル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、置換されていてもよいベンゾイル基、置換されていてもよいＣ１－Ｃ６アルキル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６アルキル基）、置換されていてもよいＣ１－Ｃ６ハロアルキル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６ハロアルキル基）、置換されていてもよいＣ１－Ｃ６アルキルカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６アルキルカルボニル基）、置換されていてもよいＣ１－Ｃ６ハロアルキルカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６ハロアルキルカルボニル基）、置換されていてもよいＣ１－Ｃ６アルコキシカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６アルコキシカルボニル基）、置換されていてもよいＣ１－Ｃ６ハロアルコキシカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６ハロアルコキシカルボニル基）、置換されていてもよいＣ１－Ｃ６アルキルアミノカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６アルキルアミノカルボニル基）、置換されていてもよいＣ１－Ｃ６ハロアルキルアミノカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６ハロアルキルアミノカルボニル基）を表す。また、Ｒ４は、場合により、置換されていてもよいヘテロシクリル基、置換されていてもよいフラニル基、置換されていてもよいチエニル基、置換されていてもよいピロリル基、置換されていてもよいピラゾリル基、置換されていてもよいイミダゾリル基、置換されていてもよい１，２，３－トリアゾリル基、置換されていてもよい１，２，４－トリアゾリル基、置換されていてもよいオキサゾリル基、置換されていてもよいイソオキサゾリル基、置換されていてもよいチアゾリル基、置換されていてもよいイソチアゾリル基、置換されていてもよい１，２，３－オキサジアゾリル基、置換されていてもよい１，２，４－オキサジアゾリル基、置換されていてもよい１，３，４－オキサジアゾリル基、置換されていてもよい１，２，５－オキサジアゾリル基、置換されていてもよい１，２，３－チアジアゾリル基、置換されていてもよい１，２，４－チアジアゾリル基、置換されていてもよい１，３，４－チアジアゾリル、置換されていてもよい１，２，５－チアジアゾリル基、置換されていてもよいピリジル基、置換されていてもよいピリミジニル基、置換されていてもよいピリダジニル基、置換されていてもよいピラジニル基、置換されていてもよい１，２，３－トリアジニル基、置換されていてもよい１，２，４－トリアジニル基、置換されていてもよい１，３，５－トリアジニル基、置換されていてもよいベンゾフリル基、置換されていてもよいベンゾイソフリル基、置換されていてもよいベンゾチエニル基、置換されていてもよいベンゾイソチエニル基、置換されていてもよいインドリル基、置換されていてもよいイソインドリル基、置換されていてもよいインダゾリル基、置換されていてもよいベンゾチアゾリル基、置換されていてもよいベンゾイソチアゾリル基、置換されていてもよいベンゾオキサゾリル基、置換されていてもよいベンゾイソオキサゾリル基、置換されていてもよいベンゾイミダゾリル基、置換されていてもよい２，１，３－ベンゾオキサジアゾール基、置換されていてもよいキノリニル基、置換されていてもよいイソキノリニル基、置換されていてもよいシンノリニル基、置換されていてもよいフタラジニル基、置換されていてもよいキナゾリニル基、置換されていてもよいキノキサリニル基、置換されていてもよいナフチリジニル基、置換されていてもよいベンゾトリアジニル基、置換されていてもよいプリニル基、置換されていてもよいプテリジニル基、置換されていてもよいインドリジニル基、又はシアノ基、ニトロ基、ハロアルコキシ基、若しくはヘテロシクリル基で置換されているアリール基を表す。｝
（ただし、Ａ１が窒素原子かつＡ２が硫黄原子かつＱが酸素原子かつｎが０の場合、Ｒ４は置換されていてもよいヘテロシクリル基、置換されていてもよいフラニル基、置換されていてもよいチエニル基、置換されていてもよいピロリル基、置換されていてもよいピラゾリル基、置換されていてもよいイミダゾリル基、置換されていてもよい１，２，３－トリアゾリル基、置換されていてもよい１，２，４－トリアゾリル基、置換されていてもよいオキサゾリル基、置換されていてもよいイソオキサゾリル基、置換されていてもよいチアゾリル基、置換されていてもよいイソチアゾリル基、置換されていてもよい１，２，３－オキサジアゾリル基、置換されていてもよい１，２，４－オキサジアゾリル基、置換されていてもよい１，３，４－オキサジアゾリル基、置換されていてもよい１，２，５－オキサジアゾリル基、置換されていてもよい１，２，３－チアジアゾリル基、置換されていてもよい１，２，４－チアジアゾリル基、置換されていてもよい１，３，４－チアジアゾリル、置換されていてもよい１，２，５－チアジアゾリル基、置換されていてもよいピリジル基、置換されていてもよいピリミジニル基、置換されていてもよいピリダジニル基、置換されていてもよいピラジニル基、置換されていてもよい１，２，３－トリアジニル基、置換されていてもよい１，２，４－トリアジニル基、置換されていてもよい１，３，５－トリアジニル基、置換されていてもよいベンゾフリル基、置換されていてもよいベンゾイソフリル基、置換されていてもよいベンゾチエニル基、置換されていてもよいベンゾイソチエニル基、置換されていてもよいインドリル基、置換されていてもよいイソインドリル基、置換されていてもよいインダゾリル基、置換されていてもよいベンゾチアゾリル基、置換されていてもよいベンゾイソチアゾリル基、置換されていてもよいベンゾオキサゾリル基、置換されていてもよいベンゾイソオキサゾリル基、置換されていてもよいベンゾイミダゾリル基、置換されていてもよい２，１，３－ベンゾオキサジアゾール基、置換されていてもよいキノリニル基、置換されていてもよいイソキノリニル基、置換されていてもよいシンノリニル基、置換されていてもよいフタラジニル基、置換されていてもよいキナゾリニル基、置換されていてもよいキノキサリニル基、置換されていてもよいナフチリジニル基、置換されていてもよいベンゾトリアジニル基、置換されていてもよいプリニル基、置換されていてもよいプテリジニル基、置換されていてもよいインドリジニル基、又はシアノ基、ニトロ基、ハロアルコキシ基、若しくはヘテロシクリル基で置換されているアリール基であることはない。また、Ａ１が窒素原子かつＡ２が硫黄原子かつＡ３が炭素原子かつＲ２がメチル基かつＱがＮＲ５かつＲ５が水素原子の場合、Ｒ４はメトキシカルボニル基であることはない。）
で表される、複素環化合物又はその塩である。　　　 R 4 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1 -C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkylaminocarbonyl group, optionally substituted phenylaminocarbonyl group, C1-C6 Haloalkylaminocarbonyl group, di (C1-C6 alkyl) aminocarbonyl group, (C1-C6 alkyl) (C1-C6 haloalkyl) aminocarbonyl group, di (C1-C6 haloalkyl) aminocarbonyl group, C1-C6 alkoxy group, C1 -C6 halo Alkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, optionally substituted benzoyl group, optionally substituted C1-C6 alkyl group (Preferably C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, Or a C1-C6 alkyl group substituted with a C1-C6 haloalkylsulfonyl group), an optionally substituted C1-C6 haloalkyl group (preferably a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group) C1-C6 Al Rusulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, or C1-C6 haloalkyl group substituted with C1-C6 haloalkylsulfonyl group), optionally substituted C1 -C6 alkylcarbonyl group (preferably C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1- A C6-haloalkylsulfinyl group or a C1-C6 alkylcarbonyl group substituted with a C1-C6 haloalkylsulfonyl group), an optionally substituted C1-C6 haloalkylcarbonyl group (preferably a C1-C6 alkoxy group, a C1-C6 group) C1-C6 substituted with an alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylsulfonyl group C6-haloalkylcarbonyl group), optionally substituted C1-C6 alkoxycarbonyl group (preferably C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6) An alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 alkoxycarbonyl group substituted with a C1-C6 haloalkylsulfonyl group), an optionally substituted C1-C6 halo Alkoxycarbonyl group (preferably C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkyl group) A sulfinyl group, or a C1-C6 haloalkoxycarbonyl group substituted with a C1-C6 haloalkylsulfonyl group), an optionally substituted C1-C6 alkylaminocarbonyl group (preferably a C1-C6 alkoxy group, a C1-C6 haloalkoxy group) A C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylsulfonyl group. C1-C6 alkylaminocarbonyl group), an optionally substituted C1-C6 haloalkylaminocarbonyl group (preferably a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkyl group) A sulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylaminocarbonyl group substituted with a C1-C6 haloalkylsulfonyl group). R 4 is optionally substituted heterocyclyl group, optionally substituted furanyl group, optionally substituted thienyl group, optionally substituted pyrrolyl group, or optionally substituted. A good pyrazolyl group, an optionally substituted imidazolyl group, an optionally substituted 1,2,3-triazolyl group, an optionally substituted 1,2,4-triazolyl group, an optionally substituted oxazolyl Group, optionally substituted isoxazolyl group, optionally substituted thiazolyl group, optionally substituted isothiazolyl group, optionally substituted 1,2,3-oxadiazolyl group, optionally substituted 1,2,4-oxadiazolyl group, 1,3,4-oxadiazolyl group which may be substituted, 1,2,5-oxy group which may be substituted A sadiazolyl group, an optionally substituted 1,2,3-thiadiazolyl group, an optionally substituted 1,2,4-thiadiazolyl group, an optionally substituted 1,3,4-thiadiazolyl group, a substituted 1,2,5-thiadiazolyl group which may be substituted, pyridyl group which may be substituted, pyrimidinyl group which may be substituted, pyridazinyl group which may be substituted, pyrazinyl group which may be substituted, substituted 1,2,3-triazinyl group which may be substituted, 1,2,4-triazinyl group which may be substituted, 1,3,5-triazinyl group which may be substituted, benzofuryl which may be substituted Group, benzoisofuryl group which may be substituted, benzothienyl group which may be substituted, benzoisothienyl group which may be substituted, A good indolyl group, an optionally substituted isoindolyl group, an optionally substituted indazolyl group, an optionally substituted benzothiazolyl group, an optionally substituted benzoisothiazolyl group, an optionally substituted benzo An oxazolyl group, an optionally substituted benzoisoxazolyl group, an optionally substituted benzimidazolyl group, an optionally substituted 2,1,3-benzooxadiazole group, an optionally substituted Good quinolinyl group, optionally substituted isoquinolinyl group, optionally substituted cinnolinyl group, optionally substituted phthalazinyl group, optionally substituted quinazolinyl group, optionally substituted quinoxalinyl group, substituted Optionally substituted naphthyridinyl group, optionally substituted benzotriazinyl group, Which may be purinyl group, a substituted pteridinyl group, an optionally substituted indolizinyl group, or a cyano group, a nitro group, a haloalkoxy group, or an aryl group substituted with a heterocyclyl group. }
(However, when A 1 is a nitrogen atom, A 2 is a sulfur atom, Q is an oxygen atom, and n is 0, R 4 is an optionally substituted heterocyclyl group, an optionally substituted furanyl group, or a substituted An optionally substituted thienyl group, an optionally substituted pyrrolyl group, an optionally substituted pyrazolyl group, an optionally substituted imidazolyl group, an optionally substituted 1,2,3-triazolyl group, a substituted 1,2,4-triazolyl group which may be substituted, oxazolyl group which may be substituted, isoxazolyl group which may be substituted, thiazolyl group which may be substituted, isothiazolyl group which may be substituted, substituted 1,2,3-oxadiazolyl group which may be substituted, 1,2,4-oxadiazolyl group which may be substituted, 1,3,4 which may be substituted An oxadiazolyl group, an optionally substituted 1,2,5-oxadiazolyl group, an optionally substituted 1,2,3-thiadiazolyl group, an optionally substituted 1,2,4-thiadiazolyl group, a substituted 1,3,4-thiadiazolyl which may be substituted, 1,2,5-thiadiazolyl which may be substituted, pyridyl which may be substituted, pyrimidinyl which may be substituted, A good pyridazinyl group, an optionally substituted pyrazinyl group, an optionally substituted 1,2,3-triazinyl group, an optionally substituted 1,2,4-triazinyl group, an optionally substituted 1 , 3,5-triazinyl group, benzofuryl group which may be substituted, benzoisofuryl group which may be substituted, benzothienyl group which may be substituted An optionally substituted benzoisothienyl group, an optionally substituted indolyl group, an optionally substituted isoindolyl group, an optionally substituted indazolyl group, an optionally substituted benzothiazolyl group, a substituted Optionally substituted benzoisothiazolyl group, optionally substituted benzoxazolyl group, optionally substituted benzisoxazolyl group, optionally substituted benzimidazolyl group, optionally substituted 2 1,3-benzooxadiazole group, optionally substituted quinolinyl group, optionally substituted isoquinolinyl group, optionally substituted cinnolinyl group, optionally substituted phthalazinyl group, substituted Quinazolinyl group which may be substituted, quinoxalinyl group which may be substituted, naphthyl which may be substituted Lysinyl group, optionally substituted benzotriazinyl group, optionally substituted purinyl group, optionally substituted pteridinyl group, optionally substituted indolizinyl group, or cyano group, nitro group, halo It is not an aryl group substituted by an alkoxy group or a heterocyclyl group. Also, A1 is nitrogen atom and A2 is sulfur atom and A3 is a methyl group and Q is a carbon atom and R2 is the case of NR 5 and R 5 is a hydrogen atom, R 4 is not a methoxy group. )
Or a salt thereof.
　ここで、本発明において使用される文言は、その定義においてそれぞれ以下に説明されるような意味を有する。 Here, the terms used in the present invention have the meanings described below in their definitions.
　「ハロゲン原子」とはフッ素原子、塩素原子、臭素原子又はヨウ素原子を示す。
　「Ｃａ－Ｃｂ（ａ、ｂは１以上の整数を表す）」との表記は、その直後に記載される置換基における炭素数の範囲を規定し、例えば、「Ｃ１－Ｃ３」とは炭素原子数が１～３個であることを意味し、「Ｃ２－Ｃ６」とは炭素原子数が２～６個であることを意味し、「Ｃ１－Ｃ６」とは炭素原子数が１～６個であることを意味する。
「ｎ－」とはノルマルを意味し、「ｉ－」はイソを意味し、「ｓ－」はセカンダリーを意味し、「ｔ－」はターシャリーを意味する “Halogen atom” refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
The notation “Ca—Cb (a, b represents an integer of 1 or more)” defines the range of the number of carbon atoms in the substituent described immediately thereafter. For example, “C1-C3” is a carbon atom. The number means 1 to 3, “C2-C6” means 2 to 6 carbon atoms, and “C1-C6” means 1 to 6 carbon atoms. Means that
“N-” means normal, “i-” means iso, “s-” means secondary, “t-” means tertiary.
　「置換されていてもよい」とは、その文言の直後の置換基がさらに置換されている場合と置換されていない場合の両方を含んでいることを示す。
　その置換基とは、水素原子、ハロゲン原子、ヒドロキシ基、シアノ基、ニトロ基、Ｃ１－Ｃ６アルキル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、Ｃ１－Ｃ６アルキルカルボニル基、Ｃ１－Ｃ６ハロアルキルカルボニル基、Ｃ１－Ｃ６アルコキシカルボニル基、Ｃ１－Ｃ６ハロアルコキシカルボニル基、Ｃ１－Ｃ６アルキルカルボニルオキシ基、Ｃ１－Ｃ６ハロアルキルカルボニルオキシ基、アミノ基、Ｃ１－Ｃ６アルキルアミノ基、ジＣ１－Ｃ６アルキルアミノ基、フェニル基を意味する。 The term “which may be substituted” indicates that the substituent immediately after the word includes both a case where the substituent is further substituted and a case where the substituent is not substituted.
The substituent includes a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group. Group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkylamino group, Phenyl It means.
　また、「Ｃ１－Ｃ３アルキル基」とは例えば、メチル、エチル、ｎ－プロピル、ｉ－プロピルなどの直鎖状または分岐鎖状の炭素原子数１～３個のアルキル基を示す。「Ｃ１－Ｃ４アルキル基」とは「Ｃ１－Ｃ３アルキル基」に加えて例えば、ｎ－ブチル、ｓ－ブチル、ｉ－ブチル、ｔ－ブチルなどの直鎖状または分岐鎖状の炭素原子数１～４個のアルキル基を示す。「Ｃ１－Ｃ６アルキル基」とは「Ｃ１－Ｃ４アルキル基」に加えて例えば、ｎ－ペンチル、２－ペンチル、３－ペンチル、ネオペンチル、ｎ－ヘキシル、２－ヘキシル、４－メチル－２－ペンチル、３－メチル－ｎ－ペンチルなどの直鎖状又は分岐鎖状の炭素原子数１～６個のアルキル基を示す。 The “C1-C3 alkyl group” refers to a linear or branched alkyl group having 1 to 3 carbon atoms such as methyl, ethyl, n-propyl, i-propyl and the like. The “C1-C4 alkyl group” means, for example, a linear or branched carbon atom such as n-butyl, s-butyl, i-butyl, t-butyl, etc. in addition to the “C1-C3 alkyl group”. Shows up to 4 alkyl groups. “C1-C6 alkyl group” means, for example, n-pentyl, 2-pentyl, 3-pentyl, neopentyl, n-hexyl, 2-hexyl, 4-methyl-2-pentyl in addition to “C1-C4 alkyl group” And a linear or branched alkyl group having 1 to 6 carbon atoms such as 3-methyl-n-pentyl.
　「Ｃ１－Ｃ６ハロアルキル基」とは例えば、モノフルオロメチル、ジフルオロメチル、トリフルオロメチル、モノクロロメチル、ジクロロメチル、トリクロロメチル、モノブロモメチル、ジブロモメチル、トリブロモメチル、１－フルオロエチル、２－フルオロエチル、２，２－ジフルオロエチル、２，２，２－トリフルオロエチル、１－クロロエチル、２－クロロエチル、２，２－ジクロロエチル、２，２，２－トリクロロエチル、１－ブロモエチル、２－ブロモエチル、２，２－ジブロモエチル、２，２，２－トリブロモエチル、２－ヨードエチル、ペンタフルオロエチル、３－フルオロ－ｎ－プロピル、３－クロロ－ｎ－プロピル、３－ブロモ－ｎ－プロピル、１，３－ジフルオロ－２－プロピル、１，３－ジクロロ－２－プロピル、１，１，１－トリフルオロ－２－プロピル、１－クロロ－３－フルオロ－２－プロピル、１，１，１，３，３，３－ヘキサフルオロ－２－プロピル、１，１，１，３，３，３－ヘキサフルオロ－２－クロロー２－プロピル、２，２，３，３，３－ペンタフルオロ－ｎ－プロピル、ヘプタフルオロ－ｉ－プロピル、ヘプタフルオロ－ｎ－プロピル、４－フルオロ－ｎ－ブチル、ノナフルオロ－ｎ－ブチル、ノナフルオロ－２－ブチルなどの同一又は異なっていてもよい１以上のハロゲン原子によって置換された直鎖状又は分岐鎖状の炭素原子数１～６個のアルキル基を示す。 “C1-C6 haloalkyl group” means, for example, monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, 1-fluoroethyl, 2-fluoro Ethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-chloroethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 1-bromoethyl, 2-bromoethyl 2,2-dibromoethyl, 2,2,2-tribromoethyl, 2-iodoethyl, pentafluoroethyl, 3-fluoro-n-propyl, 3-chloro-n-propyl, 3-bromo-n-propyl, 1,3-difluoro-2-propyl, 1,3-dichloro-2-propyl 1,1,1-trifluoro-2-propyl, 1-chloro-3-fluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 1,1,1, 3,3,3-hexafluoro-2-chloro-2-propyl, 2,2,3,3,3-pentafluoro-n-propyl, heptafluoro-i-propyl, heptafluoro-n-propyl, 4-fluoro 1 to 6 linear or branched carbon atoms substituted by one or more halogen atoms which may be the same or different, such as n-butyl, nonafluoro-n-butyl, nonafluoro-2-butyl, etc. An alkyl group is shown.
　「Ｃ２－Ｃ６アルケニル基」とは例えば、ビニル、アリル、２－ブテニル、３－ブテニルなどの炭素鎖の中に二重結合を有する炭素原子数２～４個のアルケニル基を示し、「Ｃ２－Ｃ４ハロアルケニル基」とは例えば、３，３－ジフルオロ－２－プロペニル、３，３－ジクロロ－２－プロペニル、３，３－ジブロモ－２－プロペニル、２，３－ジブロモ－２－プロペニル、４，４－ジフルオロ－３－ブテニル、３，４，４－トリブロモ－３－ブテニルなどの同一又は異なっていてもよい１以上のハロゲン原子によって置換された炭素鎖の中に二重結合を有する直鎖状又は分岐鎖状の炭素原子数２～６個のアルケニル基を示す。 The “C2-C6 alkenyl group” refers to an alkenyl group having 2 to 4 carbon atoms having a double bond in a carbon chain such as vinyl, allyl, 2-butenyl, 3-butenyl, etc. Examples of the “C4 haloalkenyl group” include 3,3-difluoro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 2,3-dibromo-2-propenyl, 4 Straight chain having a double bond in a carbon chain substituted by one or more halogen atoms, which may be the same or different, such as 1,4-difluoro-3-butenyl, 3,4,4-tribromo-3-butenyl, etc. Or a branched alkenyl group having 2 to 6 carbon atoms.
　「Ｃ２－Ｃ６アルキニル基」とは例えば、プロパルギル、１－ブチン－３－イル、１－ブチン－３－メチル－３－イルなどの炭素鎖の中に三重結合を有する直鎖状又は分岐鎖状の炭素原子数２～６個のアルキニル基を示し、「Ｃ２－Ｃ６ハロアルキニル基」とは例えば、同一又は異なっていてもよい１以上のハロゲン原子によって置換された炭素鎖の中に三重結合を有する直鎖状又は分岐鎖状の炭素原子数２～６個のアルケニル基を示す。 The “C2-C6 alkynyl group” is, for example, a linear or branched chain having a triple bond in a carbon chain such as propargyl, 1-butyn-3-yl, 1-butyn-3-methyl-3-yl, etc. An alkynyl group having 2 to 6 carbon atoms, and the “C2-C6 haloalkynyl group” includes, for example, a triple bond in a carbon chain substituted by one or more halogen atoms which may be the same or different. And a linear or branched alkenyl group having 2 to 6 carbon atoms.
　「Ｃ３－Ｃ６シクロアルキル基」とは例えば、シクロプロピル、シクロブチル、シクロペンチル、２－メチルシクロペンチル、３－メチルシクロペンチル、シクロヘキシルなどの環状構造を有する炭素原子数３～６個のシクロアルキル基を示す。 “C3-C6 cycloalkyl group” means, for example, a cycloalkyl group having 3 to 6 carbon atoms having a cyclic structure such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl and the like.
　「Ｃ１－Ｃ６アルコキシ基」とは例えば、メトキシ、エトキシ、ｎ－プロピルオキシ、イソプロピルオキシなどの直鎖状又は分岐鎖状の炭素原子数１～６個のアルコキシ基を示し、「Ｃ１－Ｃ６ハロアルコキシ基」とは例えば、トリフルオロメトキシ、１，１，１，３，３，３－ヘキサフルオロ－２－プロピルオキシ、２，２，２－トリフルオロエトキシ、２－クロロエトキシ，３－フルオロ－ｎ－プロピルオキシ、１，１，１，３，３，４，４，４－オクタフルオロ－２－ブチルオキシなどの同一又は異なっていてもよい１個以上のハロゲン原子により置換された直鎖状又は分岐鎖状の炭素原子数１～６個のハロアルコキシ基を示す。 The “C1-C6 alkoxy group” is, for example, a linear or branched alkoxy group having 1 to 6 carbon atoms such as methoxy, ethoxy, n-propyloxy, isopropyloxy, etc., and “C1-C6 halo” Examples of the “alkoxy group” include trifluoromethoxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 3-fluoro- n-propyloxy, 1,1,1,3,3,4,4,4-octafluoro-2-butyloxy and the like linear or substituted by one or more halogen atoms which may be the same or different A branched haloalkoxy group having 1 to 6 carbon atoms is shown.
　「Ｃ１－Ｃ６アルキルチオ基」とは例えば、メチルチオ、エチルチオ、ｎ－プロピルチオ、ｉ－プロピルチオ、シクロプロピルチオ、ｎ－ブチルチオ、ｉ－ブチルチオ、ｓ－ブチルチオ、ｔ－ブチルチオ、シクロプロピルメチルチオなどの直鎖状、分岐鎖状又は環状の炭素原子数１～６個のアルキルチオ基を示す。　　　 Examples of the “C1-C6 alkylthio group” include linear chains such as methylthio, ethylthio, n-propylthio, i-propylthio, cyclopropylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, cyclopropylmethylthio, etc. Or a branched or cyclic alkylthio group having 1 to 6 carbon atoms. *
　「Ｃ１－Ｃ６ハロアルキルチオ基」とは例えば、トリフルオロメチルチオ、ペンタフルオロエチルチオ、２，２，２－トリフルオロエチルチオ、ヘプタフルオロ－ｎ－プロピルチオ、ヘプタフルオロ－ｉ－プロピルチオ、ノナフルオロ－ｎ－ブチルチオ、ノナフルオロ－ｓ－ブチルチオ、４，４，４－トリフルオロ－ｎ－ブチルチオなどの同一又は異なっていてもよい１個以上のハロゲン原子により置換された直鎖状又は分岐鎖状の炭素原子数１～６個のアルキルチオ基を示す。 Examples of the “C1-C6 haloalkylthio group” include trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio, nonafluoro-n- Linear or branched carbon atoms substituted by one or more halogen atoms which may be the same or different, such as butylthio, nonafluoro-s-butylthio, 4,4,4-trifluoro-n-butylthio, etc. 1 to 6 alkylthio groups are shown.
　「Ｃ１－Ｃ６アルキルスルフィニル基」とは例えば、メチルスルフィニル、エチルスルフィニル、ｎ－プロピルスルフィニル、ｉ－プロピルスルフィニル、シクロプロピルスルフィニルなどの直鎖状、分岐鎖状又は環状の炭素原子数１～６個のアルキルスルフィニル基を示す。 “C1-C6 alkylsulfinyl group” means, for example, straight, branched or cyclic carbon atoms of 1 to 6 carbon atoms such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, cyclopropylsulfinyl, etc. Of the alkylsulfinyl group.
　「Ｃ１－Ｃ６ハロアルキルスルフィニル基」とは例えば、トリフルオロメチルスルフィニル、ペンタフルオロエチルスルフィニル、２，２，２－トリフルオロエチルスルフィニル、ヘプタフルオロ－ｎ－プロピルスルフィニル、ヘプタフルオロ－ｉ－プロピルスルフィニルなどの同一又は異なっていてもよい１個以上のハロゲン原子により置換された直鎖状又は分岐鎖状の炭素原子数１～６個のアルキルスルフィニル基を示す。 Examples of the “C1-C6 haloalkylsulfinyl group” include trifluoromethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, heptafluoro-n-propylsulfinyl, heptafluoro-i-propylsulfinyl and the like. A linear or branched alkylsulfinyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
　「Ｃ１－Ｃ６アルキルスルホニル基」とは例えば、メチルスルホニル、エチルスルホニル、ｎ－プロピルスルホニル、ｉ－プロピルスルホニル、シクロプロピルスルホニルなどの直鎖状、分岐鎖状又は環状の炭素原子数１～６個のアルキルスルホニル基を示し、「Ｃ１－Ｃ６ハロアルキルスルホニル基」とは例えば、トリフルオロメチルスルホニル、ペンタフルオロエチルスルホニル、２，２，２－トリフルオロエチルスルホニル、ヘプタフルオロ－ｎ－プロピルスルホニル、ヘプタフルオロ－ｉ－プロピルスルホニルなどの同一又は異なっていてもよい１個以上のハロゲン原子により置換された直鎖状又は分岐鎖状の炭素原子数１～６個のアルキルスルホニル基を示す。 “C1-C6 alkylsulfonyl group” means, for example, straight, branched or cyclic carbon atoms of 1 to 6 carbon atoms such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, cyclopropylsulfonyl, etc. The “C1-C6 haloalkylsulfonyl group” means, for example, trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro -Represents a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, such as i-propylsulfonyl.
　「Ｃ１－Ｃ６ハロアルキルスルホニル基」とは例えば、トリフルオロメチルスルホニル、ペンタフルオロエチルスルホニル、２，２，２－トリフルオロエチルスルホニル、ヘプタフルオロ－ｎ－プロピルスルホニル、ヘプタフルオロ－ｉ－プロピルスルホニルなどの同一又は異なっていてもよい１個以上のハロゲン原子により置換された直鎖状又は分岐鎖状の炭素原子数１～６個のアルキルスルホニル基を示す。 Examples of the “C1-C6 haloalkylsulfonyl group” include trifluoromethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl and the like. A linear or branched alkylsulfonyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
　「Ｃ１－Ｃ６アルキルアミノ基」とは例えば、メチルアミノ、エチルアミノ、ｎ－プロピルアミノ、ｉ－プロピルアミノ、ｎ－ブチルアミノ、シクロプロピルアミノなどの直鎖状、分岐鎖状又は環状の炭素原子数１～６個のアルキルアミノ基を示す。 “C1-C6 alkylamino group” means, for example, a linear, branched or cyclic carbon atom such as methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, cyclopropylamino, etc. A number 1 to 6 alkylamino groups are shown.
　「ジＣ１－Ｃ６アルキルアミノ基」とは例えば、ジメチルアミノ、ジエチルアミノ、Ｎ－エチル－Ｎ－メチルアミノなどの同一又は異なっていてもよい直鎖状又は分岐鎖状の炭素原子数１～６個のアルキル基２つにより置換されたアミノ基を示す。 The “di-C1-C6 alkylamino group” is, for example, a linear or branched carbon atom number of 1 to 6 which may be the same or different, such as dimethylamino, diethylamino, N-ethyl-N-methylamino and the like And an amino group substituted by two alkyl groups.
　「Ｃ１－Ｃ６アルキルカルボニル基」とは例えば、アセチル、プロピオニル、イソプロピルカルボニル、シクロプロピルカルボニルなどの直鎖状又は分岐鎖状又は環状の炭素原子数１～６個のアルキルカルボニル基を示す。「Ｃ１－Ｃ６ハロアルキルカルボニル基」とは例えば、モノフルオロアセチル、ジフルオロアセチル、トリフルオロアセチル、モノクロロアセチル、モノブロモアセチル、ペンタフルオロプロピオニル、ヘプタフルオロブチニルなどの同一又は異なっていてもよい１個以上のハロゲン原子により置換された直鎖状又は分岐鎖状の炭素原子数１～６個のアルキルカルボニル基を示す。 “C1-C6 alkylcarbonyl group” refers to a linear, branched or cyclic alkylcarbonyl group having 1 to 6 carbon atoms such as acetyl, propionyl, isopropylcarbonyl, cyclopropylcarbonyl and the like. The “C1-C6 haloalkylcarbonyl group” is, for example, one or more which may be the same or different, such as monofluoroacetyl, difluoroacetyl, trifluoroacetyl, monochloroacetyl, monobromoacetyl, pentafluoropropionyl, heptafluorobutynyl, etc. Or a straight-chain or branched alkylcarbonyl group having 1 to 6 carbon atoms substituted with a halogen atom.
　「Ｃ１－Ｃ６アルコキシカルボニル基」とは例えば、メトキシカルボニル、エトキシカルボニル、イソプロピルオキシカルボニルなどの直鎖状又は分岐鎖状の炭素原子数１～６個のアルコキシカルボニル基を示す。「Ｃ１－Ｃ６ハロアルコキシカルボニル基」とは、例えば、２－クロロエトキシカルボニル、２－ブロモエトキシカルボニル、２，２，２－トリフルオロエトキシカルボニル、２，２，２－トリクロロエトキシカルボニルなどの同一又は異なっていてもよい１個以上のハロゲン原子により置換された直鎖状又は分岐鎖状の炭素原子数１～６個のアルコキシカルボニル基を示す。 “C1-C6 alkoxycarbonyl group” means, for example, a linear or branched alkoxycarbonyl group having 1 to 6 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl and the like. “C1-C6 haloalkoxycarbonyl group” means, for example, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, etc. A linear or branched alkoxycarbonyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be different is shown.
　「Ｃ１－Ｃ６アルキルアミノカルボニル基」とは例えば、メチルカルバモイル、エチルカルバモイル、イソプロピルカルバモイルなどの直鎖状又は分岐鎖状の炭素原子数１～６個のアルキルアミノカルボニル基を示す。「Ｃ１－Ｃ６ハロアルキルアミノカルボニル基」とは例えば、２－クロロエチルカルバモイル、２－ブロモエチルカルバモイル、２，２，２－トリフルオロエチルカルバモイル、２，２，２－トリクロロエチルカルバモイル、などの同一又は異なっていてもよい１個以上のハロゲン原子により置換された直鎖状又は分岐鎖状の炭素原子数１～６個のアルキルアミノカルボニル基を示す。 “C1-C6 alkylaminocarbonyl group” refers to a linear or branched alkylaminocarbonyl group having 1 to 6 carbon atoms such as methylcarbamoyl, ethylcarbamoyl, isopropylcarbamoyl and the like. The “C1-C6 haloalkylaminocarbonyl group” is the same as, for example, 2-chloroethylcarbamoyl, 2-bromoethylcarbamoyl, 2,2,2-trifluoroethylcarbamoyl, 2,2,2-trichloroethylcarbamoyl, etc. A linear or branched alkylaminocarbonyl group having 1 to 6 carbon atoms which is substituted with one or more halogen atoms which may be different.
　「ジ（Ｃ１－Ｃ６アルキル）アミノカルボニル基」とは例えば、ジメチルカルバモイル、エチルメチルカルバモイル、ジエチルカルバモイル、ジイソプロピルカルバモイルなどの直鎖状、分岐鎖状又は環状の炭素原子数１～６個のアルキル基を二つ有するアミノカルボニル基を示す。（Ｃ１－Ｃ６アルキル）（Ｃ１－Ｃ６ハロアルキル）アミノカルボニル基とは例えば、Ｎ－（２－クロロエチル）－Ｎ－メチルカルバモイル、Ｎ－（２－ブロモエチル）－Ｎ－メチルカルバモイル、Ｎ－（２，２，２－トリフルオロエチル）－Ｎ－メチルカルバモイルなどの、直鎖状、分岐鎖状又は環状の炭素原子数１～６個のアルキル基と、同一又は異なっていてもよい１以上のハロゲン原子によって置換された直鎖状又は分岐鎖状の炭素原子数１～６個のアルキル基と、を有するアミノカルボニル基を示す。 The “di (C1-C6 alkyl) aminocarbonyl group” is, for example, a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms such as dimethylcarbamoyl, ethylmethylcarbamoyl, diethylcarbamoyl, diisopropylcarbamoyl and the like. Represents an aminocarbonyl group having two. (C1-C6 alkyl) (C1-C6 haloalkyl) aminocarbonyl group includes, for example, N- (2-chloroethyl) -N-methylcarbamoyl, N- (2-bromoethyl) -N-methylcarbamoyl, N- (2, One or more halogen atoms which may be the same or different from a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms, such as 2,2-trifluoroethyl) -N-methylcarbamoyl And an aminocarbonyl group having a linear or branched alkyl group having 1 to 6 carbon atoms substituted by
　本発明化合物において、Ｈｙは、下記式（Ｂ１）から式（Ｂ１１）のいずれかを表すことが好ましい。 In the compound of the present invention, Hy preferably represents any one of the following formulas (B 1 ) to (B 11 ).
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000016
　上記式（Ｂ１）から式（Ｂ１１）中、Ｒ２は、水素原子、ハロゲン原子、Ｃ１－Ｃ６アルキル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、又は、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルホニル基、ヒドロキシアミノ基、アシルヒドラジニル基、若しくは置換されていてもよいイミダゾイル基で置換されたＣ１－Ｃ６アルキル基を表す。＊２はＧ２への結合位置を表す。 In the above formulas (B 1 ) to (B 11 ), R 2 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, C1 -C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, or C1-C6 alkoxy group, C1- A C6-haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfonyl group, a hydroxyamino group, an acylhydrazinyl group, or a C1-C6 alkyl group substituted with an optionally substituted imidazolyl group is represented. * 2 represents a bonding position to G 2.
　Ｈｙは、式（Ｂ１）から式（Ｂ１１）の中でも、式（Ｂ１）から式（Ｂ９）であることがより好ましく、式（Ｂ１）、（Ｂ２）、（Ｂ４）、（Ｂ５）、（Ｂ６）、（Ｂ７）、（Ｂ８）又は（Ｂ９）であることがさらに好ましい。 Hy, among the formula (B 1) Formula (B 11), more preferably from formula (B 1) is a formula (B 9), formula (B 1), (B 2 ), (B 4) , (B 5 ), (B 6 ), (B 7 ), (B 8 ) or (B 9 ).
　本発明化合物は、その構造式中に、１個又は複数個の不斉炭素原子又は不斉中心を含む場合があり、２種以上の光学異性体が存在する場合もあるが、本発明は各々の光学異性体及びそれらが任意の割合で含まれる混合物をも全て包含するものである。また、本発明化合物は、その構造式中に２種以上の幾何異性体が存在する場合もあるが、本発明は各々の幾何異性体及びそれらが任意の割合で含まれる混合物をも全て包含するものである。 The compound of the present invention may contain one or more asymmetric carbon atoms or asymmetric centers in its structural formula, and there may be two or more optical isomers. And all the mixtures in which they are contained in an arbitrary ratio. In addition, the compound of the present invention may have two or more kinds of geometric isomers in the structural formula, but the present invention includes all of the geometric isomers and mixtures containing them in an arbitrary ratio. Is.
　本発明化合物の好ましい態様としては、以下の態様が挙げられる。
Figure JPOXMLDOC01-appb-C000017
 Preferred embodiments of the compound of the present invention include the following embodiments.
Figure JPOXMLDOC01-appb-C000017
｛一般式（Ｉ）中、
　Ｇ１は、窒素原子、炭素原子、又はＣＨを表す。
　Ｒ１は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１－Ｃ４アルキル基、アリル基、トリフルオロメチル基、Ｃ１－Ｃ２アルコキシ基、メチルチオ基、メチルスルフィニル基、メチルスルホニル基、ハロメチルチオ基、ハロメチルスルフィニル基、又はハロメチルスルホニル基を表す。
　ｍは、０又は１を表す。
　ｎは、０又は１を表す。 {In general formula (I),
G 1 represents a nitrogen atom, a carbon atom, or CH.
R 1 is a hydrogen atom, halogen atom, cyano group, nitro group, C1-C4 alkyl group, allyl group, trifluoromethyl group, C1-C2 alkoxy group, methylthio group, methylsulfinyl group, methylsulfonyl group, halomethylthio group Represents a halomethylsulfinyl group or a halomethylsulfonyl group.
m represents 0 or 1.
n represents 0 or 1.
　Ｈｙは、下記一般式（Ｂ０）
Figure JPOXMLDOC01-appb-C000018
で表される５員環又は６員環の芳香族環を表し（＊２はＧ２への結合位置を表す。点線はＮ及びＧ１を有する環への結合位置を表す。）、置換基Ｒ２を有してもよい。 Hy represents the following general formula (B0)
Figure JPOXMLDOC01-appb-C000018
(* 2 represents the bonding position to G2; the dotted line represents the bonding position to the ring having N and G 1 ), and the substituent R 2 may be included.
　Ｈｙは、式（Ｂ１）から式（Ｂ１１）のいずれかを表すことが好ましい。
Figure JPOXMLDOC01-appb-C000019
  Hy preferably represents any one of formulas (B 1 ) to (B 11 ).
Figure JPOXMLDOC01-appb-C000019
　上記式式（Ｂ１）から式（Ｂ１１）中、Ｒ２は、水素原子、ハロゲン原子、メチル基、ハロメチル基、メトキシ基、メチルチオ基、メチルスルフィニル基、メチルスルホニル基、ハロメチルチオ基、ハロメチルスルフィニル基、又はハロメチルスルホニル基を表す。
　Ｈｙは、上記式（Ｂ１）から式（Ｂ１１）の中でも、式（Ｂ１）から式（Ｂ９）であることがより好ましく、（Ｂ１）、（Ｂ２）、（Ｂ４）、（Ｂ５）、（Ｂ６）、（Ｂ７）、（Ｂ８）及び（Ｂ９）であることがさらに好ましい。 In the above formulas (B 1 ) to (B 11 ), R 2 is a hydrogen atom, halogen atom, methyl group, halomethyl group, methoxy group, methylthio group, methylsulfinyl group, methylsulfonyl group, halomethylthio group, halo. Represents a methylsulfinyl group or a halomethylsulfonyl group.
Among the above formulas (B 1 ) to (B 11 ), Hy is more preferably formulas (B 1 ) to (B 9 ), and (B 1 ), (B 2 ), (B 4 ) , (B 5 ), (B 6 ), (B 7 ), (B 8 ) and (B 9 ) are more preferable.
　Ｇ２は、下記一般式（Ｉ－Ｇ２）
Figure JPOXMLDOC01-appb-C000020
 G 2 represents the following general formula (IG 2 )
Figure JPOXMLDOC01-appb-C000020
　で表される置換基である（＊１はＨｙへの結合位置を表す）。
　ここで、Ｑは、酸素原子、又はＮＲ５を表す。
　Ｒ５は、水素原子、Ｃ１－Ｃ２アルキル基、又はアリル基を表す。
　Ｒ３は、水素原子、Ｃ１－Ｃ３アルキル基、ハロメチル基を表す。
　Ｒ４は、Ｃ１－Ｃ６アルキル基、Ｃ３－Ｃ６シクロアルキル基、Ｃ２－Ｃ６アルケニル基、Ｃ２－Ｃ６アルキニル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、Ｃ１－Ｃ６アルコキシカルボニル基、Ｃ１－Ｃ６ハロアルコキシカルボニル基、Ｃ１－Ｃ６アルキルカルボニル基、Ｃ１－Ｃ６ハロアルキルカルボニル基、Ｃ１－Ｃ６アルキルアミノカルボニル基、置換されていてもよいフェニルアミノカルボニル基、Ｃ１－Ｃ６ハロアルキルアミノカルボニル基、ジ（Ｃ１－Ｃ６アルキル）アミノカルボニル基、（Ｃ１－Ｃ６アルキル）（Ｃ１－Ｃ６ハロアルキル）アミノカルボニル基、ジ（Ｃ１－Ｃ６ハロアルキル）アミノカルボニル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、置換されていてもよいベンゾイル基、置換されていてもよいＣ１－Ｃ６アルキル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６アルキル基）、置換されていてもよいＣ１－Ｃ６ハロアルキル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６ハロアルキル基）、置換されていてもよいＣ１－Ｃ６アルキルカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６アルキルカルボニル基）、置換されていてもよいＣ１－Ｃ６ハロアルキルカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６ハロアルキルカルボニル基）、置換されていてもよいＣ１－Ｃ６アルコキシカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６アルコキシカルボニル基）、置換されていてもよいＣ１－Ｃ６ハロアルコキシカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６ハロアルコキシカルボニル基）、置換されていてもよいＣ１－Ｃ６アルキルアミノカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６アルキルアミノカルボニル基）、置換されていてもよいＣ１－Ｃ６ハロアルキルアミノカルボニル基（好ましくはＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６ハロアルキルアミノカルボニル基）を表すか、または、Ｒ４は、場合により、置換されていてもよいピリジル基、置換されていてもよいピリミジニル基、置換されていてもよい１，２，３－チアジアゾリル基、置換されていてもよい１，２，４－チアジアゾリル基、置換されていてもよいイソチアゾリル基、置換されていてもよい１，２，３－オキサジアゾリル基、置換されていてもよい１，２，４－オキサジアゾリル基、置換されていてもよい１，３，４－オキサジアゾリル基、置換されていてもよい１，２，５－オキサジアゾリル基、置換されていてもよい１，３，４－チアジアゾリル、置換されていてもよい１，２，５－チアジアゾリル基、を表す。
　ただし、Ａ１が窒素原子かつＡ２が硫黄原子かつＱが酸素原子かつｎが０の場合、
置換されていてもよいピリジル基、置換されていてもよいピリミジニル基、置換されていてもよい１，２，３－チアジアゾリル基、置換されていてもよい１，２，４－チアジアゾリル基、置換されていてもよいイソチアゾリル基、置換されていてもよい１，２，３－オキサジアゾリル基、置換されていてもよい１，２，４－オキサジアゾリル基、置換されていてもよい１，３，４－オキサジアゾリル基、置換されていてもよい１，２，５－オキサジアゾリル基、置換されていてもよい１，３，４－チアジアゾリル、置換されていてもよい１，２，５－チアジアゾリル基であることはなく、また、Ａ１が窒素原子かつＡ２が硫黄原子かつＡ３が炭素原子かつＲ２がメチル基かつＱがＮＲ５かつＲ５が水素原子の場合、Ｒ４はメトキシカルボニル基ことはない。｝
複素環化合物又はその塩である。 (* 1 represents the bonding position to Hy).
Here, Q represents an oxygen atom or NR 5 .
R 5 represents a hydrogen atom, a C1-C2 alkyl group, or an allyl group.
R 3 represents a hydrogen atom, a C1-C3 alkyl group, or a halomethyl group.
R 4 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1 -C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkylaminocarbonyl group, optionally substituted phenylaminocarbonyl group, C1-C6 Haloalkylaminocarbonyl group, di (C1-C6 alkyl) aminocarbonyl group, (C1-C6 alkyl) (C1-C6 haloalkyl) aminocarbonyl group, di (C1-C6 haloalkyl) aminocarbonyl group, C1-C6 alkoxy group, C1 -C6 halo Alkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, optionally substituted benzoyl group, optionally substituted C1-C6 alkyl group (Preferably C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, Or a C1-C6 alkyl group substituted with a C1-C6 haloalkylsulfonyl group), an optionally substituted C1-C6 haloalkyl group (preferably a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group) C1-C6 Al Rusulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, or C1-C6 haloalkyl group substituted with C1-C6 haloalkylsulfonyl group), optionally substituted C1 -C6 alkylcarbonyl group (preferably C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1- A C6-haloalkylsulfinyl group or a C1-C6 alkylcarbonyl group substituted with a C1-C6 haloalkylsulfonyl group), an optionally substituted C1-C6 haloalkylcarbonyl group (preferably a C1-C6 alkoxy group, a C1-C6 group) C1-C6 substituted with an alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylsulfonyl group C6-haloalkylcarbonyl group), optionally substituted C1-C6 alkoxycarbonyl group (preferably C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6) An alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 alkoxycarbonyl group substituted with a C1-C6 haloalkylsulfonyl group), an optionally substituted C1-C6 halo Alkoxycarbonyl group (preferably C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkyl group) A sulfinyl group, or a C1-C6 haloalkoxycarbonyl group substituted with a C1-C6 haloalkylsulfonyl group), an optionally substituted C1-C6 alkylaminocarbonyl group (preferably a C1-C6 alkoxy group, a C1-C6 haloalkoxy group) A C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylsulfonyl group. C1-C6 alkylaminocarbonyl group), an optionally substituted C1-C6 haloalkylaminocarbonyl group (preferably a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkyl group) A sulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylaminocarbonyl group substituted with a C1-C6 haloalkylsulfonyl group), or R 4 is an optionally substituted pyridyl group, an optionally substituted pyrimidinyl group, an optionally substituted 1,2,3-thiadiazolyl group, an optionally substituted 1,2,4 -Thiadiazolyl, optionally substituted isothiazolyl Group, 1,2,3-oxadiazolyl group which may be substituted, 1,2,4-oxadiazolyl group which may be substituted, 1,3,4-oxadiazolyl group which may be substituted, It represents an optionally substituted 1,2,5-oxadiazolyl group, an optionally substituted 1,3,4-thiadiazolyl group, and an optionally substituted 1,2,5-thiadiazolyl group.
Provided that when A 1 is a nitrogen atom, A 2 is a sulfur atom, Q is an oxygen atom and n is 0,
Optionally substituted pyridyl group, optionally substituted pyrimidinyl group, optionally substituted 1,2,3-thiadiazolyl group, optionally substituted 1,2,4-thiadiazolyl group, substituted Optionally substituted isothiazolyl group, optionally substituted 1,2,3-oxadiazolyl group, optionally substituted 1,2,4-oxadiazolyl group, optionally substituted 1,3,4-oxadiazolyl group Group, 1,2,5-oxadiazolyl group which may be substituted, 1,3,4-thiadiazolyl group which may be substituted, 1,2,5-thiadiazolyl group which may be substituted in addition, if a 1 is a nitrogen atom and a 2 is a sulfur atom and a 3 are carbon atoms and R2 a methyl group and Q is the NR 5 and R 5 a hydrogen atom, R 4 is methoxycarbonyl It is not that Le group. }
It is a heterocyclic compound or a salt thereof.
　例証として、及び、補足的に、一般式（Ｉ）で表される化合物の調製について、下記化学式スキームにおいて説明する。ここで、実施例を参照することもできる。
　下記化学式スキームにおいて、Ｒは、水素原子、ハロゲン原子、ヒドロキシ基、シアノ基、ニトロ基、Ｃ１－Ｃ６アルキル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、Ｃ１－Ｃ６アルキルカルボニル基、Ｃ１－Ｃ６ハロアルキルカルボニル基、Ｃ１－Ｃ６アルコキシカルボニル基、Ｃ１－Ｃ６ハロアルコキシカルボニル基、Ｃ１－Ｃ６アルキルカルボニルオキシ基、Ｃ１－Ｃ６ハロアルキルカルボニルオキシ基、アミノ基、Ｃ１－Ｃ６アルキルアミノ基、ジＣ１－Ｃ６アルキルアミノ基、フェニル基を意味するがこれに限るものではない。
　なお、下記化学式スキームにおいて、Ｒ１、Ｒ２、Ｒ３、Ｒ４及びＧ１は、一般式（Ｉ）中のＲ１、Ｒ２、Ｒ３、Ｒ４及びＧ１と同様である。 By way of illustration and supplement, the preparation of compounds of general formula (I) is illustrated in the following chemical scheme. Here, reference can also be made to examples.
In the following chemical formula scheme, R is a hydrogen atom, halogen atom, hydroxy group, cyano group, nitro group, C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1- C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkyl Carbonyl group, C1-C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, amino group, C1-C6 alkylamino group, di-C1-C6 alkyl Amino groups, does not means a phenyl group limited thereto.
In the following formula scheme, R 1, R 2, R 3 , R 4 and G 1 are the same as R 1, R 2, R 3 , R 4 and G 1 in the general formula (I).
（化学式スキーム１）
Figure JPOXMLDOC01-appb-C000021
 (Chemical Formula Scheme 1)
Figure JPOXMLDOC01-appb-C000021
　式（ＩＩ）で［式中、Ｒ２＝アルキル基］で表される化合物の調製は、ＤＥ２２２１６４７に従い、式（ＩＩＩ）で表されるチオアミドをα－ハロカルボニル化合物と反応させて式（ＩＩ）で表されるケトン化合物を生成させることによって実施する。式中（ＩＩ）［式中、Ｒ２は、水素を示す］で表される化合物は、ＵＳ６６０８０８７に記載されている方法に基づいて調製することができる。式中（ＩＩ）で表される化合物としては、好ましくは、実施例１に記載されているようにして合成することができる。 The preparation of the compound represented by the formula (II) [wherein R 2 = alkyl group] is carried out according to DE 2221647 by reacting the thioamide represented by the formula (III) with an α-halocarbonyl compound to formula (II) It produces by producing | generating the ketone compound represented by these. A compound represented by the formula (II) [wherein R 2 represents hydrogen] can be prepared based on the method described in US6608087. The compound represented by the formula (II) can be preferably synthesized as described in Example 1.
　反応スキーム１において示されている標準的な方法（例えば、ＤＥ２２２１６４７を参照）を使用して、式（ＩＶ）で表されるエステルを、最初に、式（Ｖ）で表されるカルボン酸に変換し、次いで、式（ＶＩ）で表される酸塩化物に変換することができる。 The ester of formula (IV) is first converted to the carboxylic acid of formula (V) using standard methods shown in reaction scheme 1 (see, for example, DE 2221647). Can then be converted to the acid chloride of formula (VI).
　次に、溶媒（例えば、ジクロロメタン又はテトラヒドロフラン）の中で、塩基（例えば、トリエチルアミン又はジイソプロピルエチルアミン）の存在下に、Ｎ，Ｏ－ジメチルヒドロキシルアミンとさらに反応させることによって、式（ＶＩＩ）で表される化合物が得られる。 It is then represented by the formula (VII) by further reaction with N, O-dimethylhydroxylamine in the presence of a base (eg triethylamine or diisopropylethylamine) in a solvent (eg dichloromethane or tetrahydrofuran). Is obtained.
　この式（ＶＩＩ）で表される化合物は、アルキル金属化合物（例えば、臭化メチルマグネシウム）と反応させることにより、式（ＩＩ）で表されるケトン化合物に変換することができる。 The compound represented by the formula (VII) can be converted to a ketone compound represented by the formula (II) by reacting with an alkyl metal compound (for example, methylmagnesium bromide).
　そして、補助塩基（例えば、トリエチルアミン）の存在下に、溶媒（例えば、エタノール）の中でのＮＨ２ＯＲ４ヒドロキシルアミン（例えば、Ｏ－メチル　ヒドロキシルアミン）との反応によって、式（ＩＩ）で表されるケトンから本発明による式（Ｉ）で表される化合物を得ることができる。好ましくは、実施例１に記載されているようにして合成することができる。 And represented by formula (II) by reaction with NH 2 OR 4 hydroxylamine (eg O-methyl hydroxylamine) in a solvent (eg ethanol) in the presence of an auxiliary base (eg triethylamine). A compound represented by the formula (I) according to the present invention can be obtained from a ketone. Preferably, it can be synthesized as described in Example 1.
（化学式スキーム２）
Figure JPOXMLDOC01-appb-C000022
 (Chemical Formula Scheme 2)
Figure JPOXMLDOC01-appb-C000022
　溶媒（例えば、エタノール）の中でのヒドロキシルアミンとの反応によって、式（ＩＩ）で表されるケトンから本発明による式（ＶＩＩＩ）で表されるオキシムを得ることができる。好ましくは、参考例１に記載されているようにして合成することができる。 The oxime represented by the formula (VIII) according to the present invention can be obtained from the ketone represented by the formula (II) by reaction with hydroxylamine in a solvent (for example, ethanol). Preferably, it can be synthesized as described in Reference Example 1.
　次に、補助塩基（例えば、トリエチルアミン）の存在下に、溶媒（例えば、Ｎ，Ｎ－ジメチルホルムアミド）の中で置換されたクロロピリミジンとの反応によって、式（ＶＩＩＩ）で表されるオキシムから本発明による式（Ｉ）で表される化合物を得ることができる。好ましくは、参考例１に記載されているようにして合成することができる。 The oxime of formula (VIII) is then reacted by reaction with a chloropyrimidine substituted in a solvent (eg N, N-dimethylformamide) in the presence of an auxiliary base (eg triethylamine). Compounds of formula (I) according to the invention can be obtained. Preferably, it can be synthesized as described in Reference Example 1.
　また、補助ルイス酸（例えば、臭化マグネシウム）、補助塩基（例えば、トリエチルアミン）の存在下に、溶媒（例えば、Ｎ，Ｎ－ジメチルホルムアミド）の中で置換された酸クロライドとの反応によって、式（ＶＩＩＩ）で表されるオキシムから本発明による式（Ｉ）で表される化合物を得ることができる。 Also, by reaction with an acid chloride substituted in a solvent (eg N, N-dimethylformamide) in the presence of an auxiliary Lewis acid (eg magnesium bromide), an auxiliary base (eg triethylamine) The compound represented by the formula (I) according to the present invention can be obtained from the oxime represented by (VIII).
　さらに、補助ルイス酸（例えば、臭化マグネシウム）、補助塩基（例えば、トリエチルアミン）の存在下に、溶媒（例えば、Ｎ，Ｎ－ジメチルホルムアミド）の中で置換されたイソシアネートとの反応によって、式（ＶＩＩＩ）で表されるオキシムから本発明による式（Ｉ）で表される化合物を得ることができる。 Furthermore, by reaction with an isocyanate substituted in a solvent (eg N, N-dimethylformamide) in the presence of an auxiliary Lewis acid (eg magnesium bromide), an auxiliary base (eg triethylamine), the formula ( The compound represented by the formula (I) according to the present invention can be obtained from the oxime represented by VIII).
　その他、溶媒（例えば、エタノール）の中でのヒドラジンとの反応によって、式（ＩＩ）で表されるケトンから本発明による式（ＩＸ）で表されるヒドラゾンを得ることができる。
　そして、補助塩基（例えば、トリエチルアミン）の存在下に、溶媒（例えば、Ｎ，Ｎ－ジメチルホルムアミド）の中で置換されたクロロピリミジンとの反応によって、式（ＩＸ）で表されるヒドラゾンから本発明による式（Ｉ）で表される化合物を得ることができる。 In addition, the hydrazone represented by the formula (IX) according to the present invention can be obtained from the ketone represented by the formula (II) by reaction with hydrazine in a solvent (for example, ethanol).
Then, the present invention is obtained from the hydrazone represented by the formula (IX) by reaction with chloropyrimidine substituted in a solvent (for example, N, N-dimethylformamide) in the presence of an auxiliary base (for example, triethylamine). To obtain a compound of formula (I).
　また、溶媒（例えば、エタノール）の中での置換ヒドラジンとの反応によって、式（ＩＩ）で表されるケトンから本発明による式（Ｉ）で表される化合物を得ることができる。 Also, the compound represented by the formula (I) according to the present invention can be obtained from the ketone represented by the formula (II) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
（化学式スキーム３）
Figure JPOXMLDOC01-appb-C000023
 (Chemical Formula Scheme 3)
Figure JPOXMLDOC01-appb-C000023
　溶媒（例えば、テトラヒドロフラン）の中で還元剤（例えば、水素化リチウムアルミニウム）との反応によって、式（ＩＶ）で表されるエステルから式（Ｘ）で表されるアルコールを得ることができる（ＷＯ２００７／３９１７２を参照）。
　次に、溶媒（例えば、酢酸エチル）の中で酸化剤（例えば、二酸化マンガン）との反応によって、式（Ｘ）で表されるアルコールから、式（ＸＩ）で表されるアルデヒドを得ることができる（ＥＰ１１８６６０４を参照）。
　そして、溶媒（例えば、テトラヒドロフラン）の中でアルキルマグネシウムクロリドとの反応によって、式（ＸＩ）で表されるアルデヒドから式（ＸＩＩ）で表されるアルコールを得ることができる（ＵＳ２００７／２４４０９４を参照 ）。
　その後、溶媒（例えば、酢酸エチル）の中で酸化剤（例えば、二酸化マンガン）との反応によって、式（ＸＩＩ）で表されるアルコールから、式（ＩＩ）で表されるケトン化合物を得ることができる（ＥＰ１１８６６０４を参照）。
　さらに、補助塩基（例えば、トリエチルアミン）の存在下に、溶媒（例えば、エタノール）の中でのＮＨ２ＯＲ４ヒドロキシルアミン（例えば、Ｏ－メチル　ヒドロキシルアミン）との反応によって、式（ＩＩ）で表されるケトンから本発明による式（Ｉ）で表される化合物を得ることができる。好ましくは、実施例１に記載されているようにして合成することができる。 The alcohol represented by the formula (X) can be obtained from the ester represented by the formula (IV) by reaction with a reducing agent (for example, lithium aluminum hydride) in a solvent (for example, tetrahydrofuran) (WO2007). / 39172).
Next, an aldehyde represented by the formula (XI) can be obtained from the alcohol represented by the formula (X) by reaction with an oxidizing agent (eg manganese dioxide) in a solvent (eg ethyl acetate). Yes (see EP 1186604).
Then, an alcohol represented by the formula (XII) can be obtained from the aldehyde represented by the formula (XI) by reaction with an alkylmagnesium chloride in a solvent (for example, tetrahydrofuran) (see US2007 / 244940). .
Thereafter, a ketone compound represented by the formula (II) can be obtained from an alcohol represented by the formula (XII) by reaction with an oxidizing agent (eg manganese dioxide) in a solvent (eg ethyl acetate). Yes (see EP 1186604).
Furthermore, by reaction with NH 2 OR 4 hydroxylamine (eg O-methyl hydroxylamine) in a solvent (eg ethanol) in the presence of an auxiliary base (eg triethylamine) The compound represented by the formula (I) according to the present invention can be obtained from the obtained ketone. Preferably, it can be synthesized as described in Example 1.
（化学式スキーム４）
Figure JPOXMLDOC01-appb-C000024
 (Chemical Formula Scheme 4)
Figure JPOXMLDOC01-appb-C000024
　式（ＸＩＩＩ）で表されるヒドラジドは、溶媒（例えば、Ｎ，Ｎ－ジメチルホルムアミド）の中で、塩基（例えば、トリエチルアミン）の存在下に、エチルオキサリルクロリドを用いて、式（ＸＩＶ）で表されるジアシルヒドラジン化合物に変換される。
　次いで、この式（ＸＩＶ）で表されるジアシルヒドラジン化合物は、硫化剤（例えば、ローソン試薬）と反応させて、式（ＸＶ）で表されるチアジアゾールに変換させる（Ｌｉｑｕｉｄ　Ｃｒｙｓｔａｌｓ　Ｔｏｄａｙ，　Ｖｏｌｕｍｅ　１４，　１，　２００５，　１５－１８を参照）。
　その後、金属アルキル化合物（例えば、メチルリチウム）との反応によって、エステル（ＸＶ）からケトン（ＸＶＩ）を得ることができる（ＵＳ２０１１／２１２９４９を参照）。
　溶媒（例えば、エタノール）の中でのヒドロキシルアミンとの反応によって、式（ＸＶＩ）で表されるケトンから本発明による式（ＸＶＩＩ）で表されるオキシムを得ることができる。
　そして、補助塩基（例えば、トリエチルアミン）の存在下に、溶媒（例えば、Ｎ，Ｎ－ジメチルホルムアミド）の中で置換されたクロロピリミジンとの反応によって、式（ＸＶＩＩ）で表されるオキシムから本発明による式（Ｉ）で表される化合物を得ることができる。
　また、溶媒（例えば、エタノール）の中での置換ヒドラジンとの反応によって、式（ＸＶＩ）で表されるケトンから本発明による式（Ｉ）で表される化合物を得ることができる。 The hydrazide represented by the formula (XIII) is represented by the formula (XIV) using ethyl oxalyl chloride in the presence of a base (for example, triethylamine) in a solvent (for example, N, N-dimethylformamide). To a diacylhydrazine compound.
Next, the diacylhydrazine compound represented by the formula (XIV) is reacted with a sulfurizing agent (for example, Lawson's reagent) to convert it into a thiadiazole represented by the formula (XV) (Liquid Crystals Today, Volume 14, 1 , 2005, 15-18).
The ketone (XVI) can then be obtained from the ester (XV) by reaction with a metal alkyl compound (eg methyl lithium) (see US 2011/1212949).
The oxime represented by formula (XVII) according to the present invention can be obtained from the ketone represented by formula (XVI) by reaction with hydroxylamine in a solvent (for example, ethanol).
The present invention can be obtained from the oxime represented by the formula (XVII) by reaction with chloropyrimidine substituted in a solvent (eg, N, N-dimethylformamide) in the presence of an auxiliary base (eg, triethylamine). To obtain a compound of formula (I).
Alternatively, the compound represented by the formula (I) according to the present invention can be obtained from the ketone represented by the formula (XVI) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
（化学式スキーム５）
Figure JPOXMLDOC01-appb-C000025
 (Chemical Formula Scheme 5)
Figure JPOXMLDOC01-appb-C000025
　式（ＸＶＩＩＩ）で表されるボロン酸は、溶媒（例えば、エチレングリコール又はジメチルエーテル）の中で、パラジウム触媒（例えば、テトラキス（トリフェニルホスフィン）パラジウム（０））、塩基（例えば、炭酸カリウム）の存在下に、アシルブロモピリジンを用いて、式（ＸＩＸ）で表されるピリジン化合物に変換され（Ｊｏｕｒｎａｌ　ｏｆ　Ｍｅｄｉｃｉｎａｌ　Ｃｈｅｍｉｓｔｒｙ，　２００５， ｖｏｌ． ４８， Ｎｏ．１，　２２４を参照）、好ましくは、実施例２に記載されているようにして合成することができる。
　次に、溶媒（例えば、エタノール）の中でのヒドロキシルアミンとの反応によって、式（ＸＩＸ）で表されるピリジルピリジン化合物から本発明による式（ＸＸ）で表されるオキシムを得ることができる。
　そして、補助塩基（例えば、トリエチルアミン）の存在下に、溶媒（例えば、Ｎ，Ｎ－ジメチルホルムアミド）の中で置換されたクロロピリミジンとの反応によって、式（ＸＸ）で表されるオキシムから本発明による式（Ｉ）で表される化合物を得ることができる。好ましくは、実施例２に記載されているようにして合成することができる。
また、溶媒（例えば、エタノール）の中での置換ヒドラジンとの反応によって、式（ＸＩＸ）で表されるケトンから本発明による式（Ｉ）で表される化合物を得ることができる。 The boronic acid represented by the formula (XVIII) is a palladium catalyst (for example, tetrakis (triphenylphosphine) palladium (0)), a base (for example, potassium carbonate) in a solvent (for example, ethylene glycol or dimethyl ether). In the presence, it is converted to a pyridine compound of formula (XIX) using acyl bromopyridine (see Journal of Medicinal Chemistry, 2005, vol. 48, No. 1, 224), preferably in the Examples Can be synthesized as described in 2.
Next, the oxime represented by the formula (XX) according to the present invention can be obtained from the pyridylpyridine compound represented by the formula (XIX) by reaction with hydroxylamine in a solvent (for example, ethanol).
The present invention can be obtained from the oxime represented by the formula (XX) by reaction with chloropyrimidine substituted in a solvent (for example, N, N-dimethylformamide) in the presence of an auxiliary base (for example, triethylamine). The compound represented by the formula (I) can be obtained. Preferably, it can be synthesized as described in Example 2.
Alternatively, the compound represented by the formula (I) according to the present invention can be obtained from the ketone represented by the formula (XIX) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
（化学式スキーム６）
Figure JPOXMLDOC01-appb-C000026
 (Chemical Formula Scheme 6)
Figure JPOXMLDOC01-appb-C000026
　式（ＸＶＩＩＩ）で表されるボロン酸は、溶媒（例えば、エチレングリコール　ジメチルエーテル）の中で、パラジウム触媒（例えば、テトラキス（トリフェニルホスフィン）パラジウム（０））、塩基（例えば、炭酸カリウム）の存在下に、アシルブロモチオフェンを用いて、式（ＸＸＩ）で表されるチオフェン化合物に変換される（Ｊｏｕｒｎａｌ　ｏｆ　Ｍｅｄｉｃｉｎａｌ　Ｃｈｅｍｉｓｔｒｙ，　２００５， ｖｏｌ． ４８， Ｎｏ．１，　２２４を参照）。
　次に、溶媒（例えば、エタノール）の中でのヒドロキシルアミンとの反応によって、式（ＸＸＩ）で表されるチオフェン化合物から本発明による式（ＸＸＩＩ）で表されるオキシムを得ることができる。
　そして、補助塩基（例えば、トリエチルアミン）の存在下に、溶媒（例えば、Ｎ，Ｎ－ジメチルホルムアミド）の中で置換されたクロロピリミジンとの反応によって、式（ＸＸＩＩ）で表されるオキシムから本発明による式（Ｉ）で表される化合物を得ることができる。
また、溶媒（例えば、エタノール）の中での置換ヒドラジンとの反応によって、式（ＸＸＩ）で表されるケトンから本発明による式（Ｉ）で表される化合物を得ることができる。 The boronic acid represented by the formula (XVIII) is present in a solvent (eg, ethylene glycol dimethyl ether) in the presence of a palladium catalyst (eg, tetrakis (triphenylphosphine) palladium (0)), a base (eg, potassium carbonate). Below, it is converted into a thiophene compound represented by the formula (XXI) using acylbromothiophene (see Journal of Medicinal Chemistry, 2005, vol. 48, No. 1, 224).
Next, the oxime represented by the formula (XXII) according to the present invention can be obtained from the thiophene compound represented by the formula (XXI) by reaction with hydroxylamine in a solvent (for example, ethanol).
The present invention can be obtained from the oxime represented by the formula (XXII) by reaction with chloropyrimidine substituted in a solvent (for example, N, N-dimethylformamide) in the presence of an auxiliary base (for example, triethylamine). To obtain a compound of formula (I).
Further, the compound represented by the formula (I) according to the present invention can be obtained from the ketone represented by the formula (XXI) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
（化学式スキーム７）
Figure JPOXMLDOC01-appb-C000027
 (Chemical Formula Scheme 7)
Figure JPOXMLDOC01-appb-C000027
　式（ＸＶＩＩＩ）で表されるボロン酸は、溶媒（例えば、エチレングリコール　ジメチルエーテル）の中で、パラジウム触媒（例えば、テトラキス（トリフェニルホスフィン）パラジウム（０））、塩基（例えば、炭酸カリウム）の存在下に、アシルブロモフランを用いて、式（ＸＸＩＩＩ）で表されるフラン化合物に変換される（Ｊｏｕｒｎａｌ　ｏｆ　Ｍｅｄｉｃｉｎａｌ　Ｃｈｅｍｉｓｔｒｙ，　２００５， ｖｏｌ． ４８， Ｎｏ．１，　２２４を参照）。
　次に、溶媒（例えば、エタノール）の中でのヒドロキシルアミンとの反応によって、式（ＸＸＩＩＩ）で表されるピリジルフラン化合物から本発明による式（ＸＸＩＶ）で表されるオキシムを得ることができる。
　そして補助塩基（例えば、トリエチルアミン）の存在下に、溶媒（例えば、Ｎ，Ｎ－ジメチルホルムアミド）の中で置換されたクロロピリミジンとの反応によって、式（ＸＸＩＶ）で表されるオキシムから本発明による式（Ｉ）で表される化合物を得ることができる。
　また、溶媒（例えば、エタノール）の中での置換ヒドラジンとの反応によって、式（ＸＸＩＩＩ）で表されるケトンから本発明による式（Ｉ）で表される化合物を得ることができる。 The boronic acid represented by the formula (XVIII) is present in a solvent (eg, ethylene glycol dimethyl ether) in the presence of a palladium catalyst (eg, tetrakis (triphenylphosphine) palladium (0)), a base (eg, potassium carbonate). Below, it is converted into a furan compound represented by the formula (XXIII) using acyl bromofuran (see Journal of Medicinal Chemistry, 2005, vol. 48, No. 1, 224).
Next, the oxime represented by the formula (XXIV) according to the present invention can be obtained from the pyridylfuran compound represented by the formula (XXIII) by reaction with hydroxylamine in a solvent (for example, ethanol).
And according to the invention from an oxime of the formula (XXIV) by reaction with a chloropyrimidine substituted in a solvent (eg N, N-dimethylformamide) in the presence of an auxiliary base (eg triethylamine). A compound represented by the formula (I) can be obtained.
Alternatively, the compound represented by the formula (I) according to the present invention can be obtained from the ketone represented by the formula (XXIII) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
（化学式スキーム８）
Figure JPOXMLDOC01-appb-C000028
 (Scheme 8)
Figure JPOXMLDOC01-appb-C000028
　式（ＸＸＶ）で表される化合物は、溶媒（例えば、Ｎ，Ｎ－ジメチルアセタミド）の中で、パラジウム触媒（例えば、テトラキス（トリフェニルホスフィン）パラジウム（０））、塩基（例えば、炭酸カリウム）の存在下に、アシルチアゾールを用いて、式（ＸＸＶＩ）で表されるチアゾール化合物に変換される（Ｔｅｔｒａｈｅｄｒｏｎ　２０１２， ｖｏｌ．６８，７６５５を参照）。好ましくは、実施例３に記載されているようにして合成することができる。
　次に、溶媒（例えば、エタノール）の中でのヒドロキシルアミンとの反応によって、式（ＸＸＶＩ）で表されるチアゾール化合物から本発明による式（ＸＸＶＩＩ）で表されるオキシムを得ることができる。
　そして、補助塩基（例えば、トリエチルアミン）の存在下に、溶媒（例えば、Ｎ，Ｎ－ジメチルホルムアミド）の中で置換されたクロロピリミジンとの反応によって、式（ＸＸＶＩＩ）で表されるオキシムから本発明による式（Ｉ）で表される化合物を得ることができる。
　また、溶媒（例えば、エタノール）の中での置換ヒドラジンとの反応によって、式（ＸＸＶＩ）で表されるケトンから本発明による式（Ｉ）で表される化合物を得ることができる。 The compound represented by the formula (XXV) is prepared by reacting a palladium catalyst (eg, tetrakis (triphenylphosphine) palladium (0)), a base (eg, In the presence of potassium), it is converted to a thiazole compound represented by the formula (XXVI) using acyl thiazole (see Tetrahedron 2012, vol. 68, 7655). Preferably, it can be synthesized as described in Example 3.
Next, the oxime represented by the formula (XXVII) according to the present invention can be obtained from the thiazole compound represented by the formula (XXVI) by reaction with hydroxylamine in a solvent (for example, ethanol).
The present invention can be obtained from an oxime represented by the formula (XXVII) by reaction with chloropyrimidine substituted in a solvent (eg, N, N-dimethylformamide) in the presence of an auxiliary base (eg, triethylamine) The compound represented by the formula (I) can be obtained.
Alternatively, the compound represented by the formula (I) according to the present invention can be obtained from the ketone represented by the formula (XXVI) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
（化学式スキーム９）
Figure JPOXMLDOC01-appb-C000029
 (Scheme 9)
Figure JPOXMLDOC01-appb-C000029
　式（ＸＸＶＩＩＩ）で表されるエナミン化合物は、溶媒（例えば、ジクロロエタン）の中で、酸化剤（例えば、ヨードソベンゼン）の存在下に、酸化合物を用いて、式（ＸＸＩＸ）で表されるエナミン化合物に変換される（ｏｌ３０２５５８３を参照）。
　次に、式（ＸＸＩＸ）で表されるエナミン化合物は、溶媒（例えば、酢酸）の中で式（ＸＸＸ）で表されるオキサゾールに変換される（ｏｌ３０２５５８３を参照）。
　その後、溶媒（例えば、エタノール）の中でのヒドロキシルアミンとの反応によって、式（ＸＸＸ）で表されるオキサゾール化合物から本発明による式（ＸＸＸＩ）で表されるオキシムを得ることができる。
　そして、補助塩基（例えば、トリエチルアミン）の存在下に、溶媒（例えば、Ｎ，Ｎ－ジメチルホルムアミド）の中で置換されたクロロピリミジンとの反応によって、式（ＸＸＸＩ）で表されるオキシムから本発明による式（Ｉ）で表される化合物を得ることができる。
　また、溶媒（例えば、エタノール）の中での置換ヒドラジンとの反応によって、式（ＸＸＸ）で表されるケトンから本発明による式（Ｉ）で表される化合物を得ることができる。 The enamine compound represented by the formula (XXVIII) is represented by the formula (XXIX) using an acid compound in the presence of an oxidizing agent (for example, iodosobenzene) in a solvent (for example, dichloroethane). Converted to the enamine compound (see ol 3025583).
Next, the enamine compound represented by the formula (XXIX) is converted into the oxazole represented by the formula (XXX) in a solvent (for example, acetic acid) (see ol3025583).
Thereafter, the oxime represented by the formula (XXXI) according to the present invention can be obtained from the oxazole compound represented by the formula (XXX) by reaction with hydroxylamine in a solvent (for example, ethanol).
The present invention can be obtained from an oxime represented by the formula (XXXI) by reaction with a chloropyrimidine substituted in a solvent (eg, N, N-dimethylformamide) in the presence of an auxiliary base (eg, triethylamine) To obtain a compound of formula (I).
Also, the compound represented by the formula (I) according to the present invention can be obtained from the ketone represented by the formula (XXX) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
（化学式スキーム１０）
Figure JPOXMLDOC01-appb-C000030
  (Scheme 10)
Figure JPOXMLDOC01-appb-C000030
　式（ＸＸＸＩＩ）で表されるピラゾール化合物は、溶媒（例えば、Ｎ，Ｎ－ジメチルホルムアミド）の中で、金属塩（例えば、ヨウ化銅）の存在下に、ジアミン触媒を用いて、式（ＸＸＸＩＩＩ）で表される化合物に変換される。
　次に、式（ＸＸＸＩＩＩ）で表される化合物は、溶媒（例えば、メタノール／水）の中水酸化物（例えば、水酸化リチウム）を用いて、式（ＸＸＸＩＶ）で表されるカルボン酸に変換し、次いで塩素化剤（例えば、塩化チオニル）を用いて、式（ＸＸＸＶ）で表される酸塩化物に変換することができる。
次に、溶媒（例えば、ジクロロメタン又はテトラヒドロフラン）の中で、塩基（例えば、トリエチルアミン又はジイソプロピルエチルアミン）の存在下に、Ｎ，Ｏ－ジメチルヒドロキシルアミンとさらに反応させることによって、式（ＸＸＸＶＩ）で表される化合物が得られる。
この式（ＸＸＸＶＩ）で表される化合物は、アルキル金属化合物（例えば、臭化メチルマグネシウム）と反応させることにより、式（ＸＸＸＶＩＩ）で表されるケトン化合物に変換することができる。 A pyrazole compound represented by the formula (XXXII) is prepared by using a diamine catalyst in a solvent (for example, N, N-dimethylformamide) in the presence of a metal salt (for example, copper iodide). ).
Next, the compound represented by the formula (XXXIII) is converted into a carboxylic acid represented by the formula (XXXIV) using a middle hydroxide (eg, lithium hydroxide) of a solvent (eg, methanol / water). And then converted to an acid chloride of formula (XXXV) using a chlorinating agent (eg thionyl chloride).
It is then represented by the formula (XXXVI) by further reaction with N, O-dimethylhydroxylamine in the presence of a base (eg triethylamine or diisopropylethylamine) in a solvent (eg dichloromethane or tetrahydrofuran). Is obtained.
This compound represented by the formula (XXXVI) can be converted to a ketone compound represented by the formula (XXXVII) by reacting with an alkyl metal compound (for example, methylmagnesium bromide).
次に、溶媒（例えば、エタノール）の中でのヒドロキシルアミンとの反応によって、式（ＸＸＸＶＩＩ）で表されるケトン化合物から本発明による式（ＸＸＸＶＩＩＩ）で表されるオキシムを得ることができる。
　そして、補助塩基（例えば、トリエチルアミン）の存在下に、溶媒（例えば、Ｎ，Ｎ－ジメチルホルムアミド）の中で置換されたクロロピリミジンとの反応によって、式（ＸＸＸＶＩＩＩ）で表されるオキシムから本発明による式（Ｉ）で表される化合物を得ることができる。
　また、溶媒（例えば、エタノール）の中での置換ヒドラジンとの反応によって、式（ＸＸＸＶＩＩ）で表されるケトンから本発明による式（Ｉ）で表される化合物を得ることができる。　 Next, the oxime represented by the formula (XXXVIII) according to the present invention can be obtained from the ketone compound represented by the formula (XXXVII) by reaction with hydroxylamine in a solvent (for example, ethanol).
The present invention can be obtained from an oxime represented by the formula (XXXVIII) by reaction with chloropyrimidine substituted in a solvent (eg, N, N-dimethylformamide) in the presence of an auxiliary base (eg, triethylamine) To obtain a compound represented by the formula (I).
Alternatively, the compound represented by the formula (I) according to the present invention can be obtained from the ketone represented by the formula (XXXVII) by reaction with a substituted hydrazine in a solvent (for example, ethanol).
　前記に示した製造方法において、目的物は、反応終了後、反応系から常法に従って単離すればよいが、必要に応じて、再結晶、カラムクロマトグラフィー、蒸留などの操作を行い精製することができる。 In the production method shown above, the target product may be isolated from the reaction system according to a conventional method after completion of the reaction, but may be purified by operations such as recrystallization, column chromatography, and distillation as necessary. Can do.
　以下、第１表から第４表に本発明の有害生物防除剤の有効成分である一般式（Ｉ）で表される本発明化合物の代表的な化合物及び参考化合物を例示化合物として示すが、本発明化合物はこれら本発明化合物の例示化合物にに限定されるものではない。 Tables 1 to 4 below show representative compounds and reference compounds of the compounds of the present invention represented by the general formula (I), which are active ingredients of the pesticidal agent of the present invention, as exemplary compounds. Inventive compounds are not limited to these exemplified compounds of the present invention.
　なお、表中、「ｎ－」はノルマルを、「Ｍｅ」はメチル基を、「Ｅｔ」はエチル基を、「ｎ－Ｐｒ」はノルマルプロピル基を、「ｉ－Ｐｒ」はイソプロピル基を、「ｎ－Ｂｕ」はノルマルブチル基を、「ｉ－Ｂｕ」はイソブチル基を、「ｓ－Ｂｕ」はセカンダリーブチル基を、「ｔ－Ｂｕ」はターシャリーブチル基を、「Ｈ」は水素原子を、「Ｏ」は酸素原子を、「Ｓ」は硫黄原子を、「Ｃ」は炭素原子を、「Ｎ」は窒素原子を、「Ｆ」はフッ素原子を、「Ｃｌ」は塩素原子を、「Ｂｒ」は臭素原子を、「Ｉ」はヨウ素原子を、「ＣＦ３」はトリフルオロメチル基を、「ＭｅＳ」はメチルチオ基を、「ＭｅＳＯ」はメチルスルフィニル基を、「ＭｅＳＯ２」はメチルスルホニル基を、「ＭｅＯ」はメトキシ基を、「ＮＨ２」はアミノ基を、「ＭｅＮＨ」はメチルアミノ基を、「Ｍｅ２Ｎ」はジメチルアミノ基を、「ＯＨ」はヒドロキシ基を、それぞれ表すものである。 In the table, “n-” represents normal, “Me” represents a methyl group, “Et” represents an ethyl group, “n-Pr” represents a normal propyl group, “i-Pr” represents an isopropyl group, “N-Bu” represents a normal butyl group, “i-Bu” represents an isobutyl group, “s-Bu” represents a secondary butyl group, “t-Bu” represents a tertiary butyl group, and “H” represents a hydrogen atom. , “O” represents an oxygen atom, “S” represents a sulfur atom, “C” represents a carbon atom, “N” represents a nitrogen atom, “F” represents a fluorine atom, “Cl” represents a chlorine atom, “Br” is a bromine atom, “I” is an iodine atom, “CF 3 ” is a trifluoromethyl group, “MeS” is a methylthio group, “MeSO” is a methylsulfinyl group, and “MeSO 2 ” is methyl. sulfonyl group, "MeO" a methoxy group, an "NH 2" is an amino group The "MeNH" represents a methyl group, "Me 2 N" is a dimethylamino group, "OH" is a hydroxy group, and represents respectively.
（第１表） (Table 1)
Figure JPOXMLDOC01-appb-C000031
 
Figure JPOXMLDOC01-appb-C000031
 
Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000034
Figure JPOXMLDOC01-appb-T000034
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000036
Figure JPOXMLDOC01-appb-T000036
Figure JPOXMLDOC01-appb-T000037
Figure JPOXMLDOC01-appb-T000037
Figure JPOXMLDOC01-appb-T000038
Figure JPOXMLDOC01-appb-T000038
Figure JPOXMLDOC01-appb-T000039
Figure JPOXMLDOC01-appb-T000039
Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-T000041
Figure JPOXMLDOC01-appb-T000041
Figure JPOXMLDOC01-appb-T000042
Figure JPOXMLDOC01-appb-T000042
Figure JPOXMLDOC01-appb-T000043
Figure JPOXMLDOC01-appb-T000043
Figure JPOXMLDOC01-appb-T000044
Figure JPOXMLDOC01-appb-T000044
Figure JPOXMLDOC01-appb-T000045
Figure JPOXMLDOC01-appb-T000045
Figure JPOXMLDOC01-appb-T000046
Figure JPOXMLDOC01-appb-T000046
Figure JPOXMLDOC01-appb-T000047
Figure JPOXMLDOC01-appb-T000047
（第２表） (Table 2)
Figure JPOXMLDOC01-appb-C000048
 
 
Figure JPOXMLDOC01-appb-C000048
 
 
Figure JPOXMLDOC01-appb-T000049
Figure JPOXMLDOC01-appb-T000049
Figure JPOXMLDOC01-appb-T000050
Figure JPOXMLDOC01-appb-T000050
（第３表） (Table 3)
Figure JPOXMLDOC01-appb-C000051
 
 
Figure JPOXMLDOC01-appb-C000051
 
 
Figure JPOXMLDOC01-appb-T000052
Figure JPOXMLDOC01-appb-T000052
Figure JPOXMLDOC01-appb-T000053
Figure JPOXMLDOC01-appb-T000053
Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000056
Figure JPOXMLDOC01-appb-T000056
（第４表） (Table 4)
Figure JPOXMLDOC01-appb-C000057
 
Figure JPOXMLDOC01-appb-C000057
 
Figure JPOXMLDOC01-appb-T000058
  
Figure JPOXMLDOC01-appb-T000058
  
Figure JPOXMLDOC01-appb-T000059
  
Figure JPOXMLDOC01-appb-T000059
  
Figure JPOXMLDOC01-appb-T000060
  
Figure JPOXMLDOC01-appb-T000060
  
Figure JPOXMLDOC01-appb-T000061
  
Figure JPOXMLDOC01-appb-T000061
  
Figure JPOXMLDOC01-appb-T000062
  
Figure JPOXMLDOC01-appb-T000062
  
Figure JPOXMLDOC01-appb-T000063
  
Figure JPOXMLDOC01-appb-T000063
  
Figure JPOXMLDOC01-appb-T000064
  
Figure JPOXMLDOC01-appb-T000064
  
Figure JPOXMLDOC01-appb-T000065
  
Figure JPOXMLDOC01-appb-T000065
  
Figure JPOXMLDOC01-appb-T000066
  
Figure JPOXMLDOC01-appb-T000066
  
Figure JPOXMLDOC01-appb-T000067
  
Figure JPOXMLDOC01-appb-T000067
  
Figure JPOXMLDOC01-appb-T000068
  
Figure JPOXMLDOC01-appb-T000068
  
　本発明化合物は、農園芸作物及び樹木等を加害する各種農業場面において防除対象となる有害生物に対して防除効果を示す。
　したがって、本発明化合物は、上述した本発明化合物を有効成分として含有することにより、高い殺虫効果を有する有害生物防除剤や農園芸用有害生物防除剤となる。
　また、本発明化合物は、植物種子に適用することにより、播種後の植物に発生する農業害虫等の有害生物による被害を予防することが出来る。また、本発明化合物は、倉庫に貯蔵された穀物等を加害する貯穀害虫に対して防除効果を示す。また、本発明化合物は、建築物、家具、貯蔵木材等の木材を加害する木材食害虫等の昆虫類に対して防除効果を示す。また、本発明化合物は、家屋等の人間の生活環境で悪影響を与える衛生害虫に対して防除効果を有する。また、本発明化合物は、哺乳動物及び鳥類の外部又は内部寄生虫に対して防除効果を有する。また、同様の場面で発生、加害するダニ類、甲殻類、軟体動物、線虫類の何れの有害生物も低濃度で有効に防除できる。 The compound of the present invention exhibits a controlling effect against pests to be controlled in various agricultural scenes that damage agricultural and horticultural crops and trees.
Therefore, this invention compound turns into the pest control agent which has a high insecticidal effect, and the agricultural and horticultural pest control agent by containing this invention compound mentioned above as an active ingredient.
Moreover, this invention compound can prevent the damage by pests, such as agricultural pests which generate | occur | produce in the plant after sowing, by applying to a plant seed. Moreover, this invention compound shows the control effect with respect to the stored grain pest which harms the grain etc. which were stored in the warehouse. Moreover, this invention compound shows a control effect with respect to insects, such as a wood-eating insect, which harms wood, such as a building, furniture, and storage wood. Moreover, this invention compound has a control effect with respect to the sanitary insect pest which has a bad influence in human living environment, such as a house. Moreover, this invention compound has a control effect with respect to the external or internal parasite of a mammal and birds. Moreover, it is possible to effectively control pests such as mites, crustaceans, molluscs, and nematodes that occur and harm in the same scene at low concentrations.
　本発明化合物を用いて防除しうる昆虫類、ダニ類、甲殻類、軟体動物及び線虫類には具体的に、例えば、チャノコカクモンハマキ（Ａｄｏｘｏｐｈｙｅｓ　ｈｏｎｍａｉ）、リンゴコカクモンハマキ（Ａｄｏｘｏｐｈｙｅｓ　ｏｒａｎａ　ｆａｃｉａｔａ）、リンゴモンハマキ（Ａｒｃｈｉｐｓ　ｂｒｅｖｉｐｌｉｃａｎｕｓ）、リンゴコシンクイガ（Ｇｒａｐｈｏｌｉｔａ　ｉｎｏｐｉｎａｔａ）、ミダレカクモンハマキ（Ａｒｃｈｉｐｓ　ｆｕｓｃｏｃｕｐｒｅａｎｕｓ）、ナシヒメシンクイ（Ｇｒａｐｈｏｌｉｔａ　ｍｏｌｅｓｔａ）、チャハマキ（Ｃｈｏｒｉｓｔｏｎｅｕｒａ　ｍａｇｎａｎｉｍａ）、マメシンクイガ（Ｌｅｇｕｍｉｎｉｖｏｒａ　ｇｌｙｃｉｎｉｖｏｒｅｌｌａ）、クワヒメハマキ（Ｏｌｅｔｈｒｅｕｔｅｓ　ｍｏｒｉ）、リンゴハマキホソガ（Ｃａｌｏｐｔｉｌｉａ　ｚａｃｈｒｙｓａ）、リンゴヒメシンクイ（Ａｒｇｙｒｅｓｔｈｉａ　ｃｏｎｊｕｇｅｌｌａ）、ナシホソガ（Ｓｐｕｌｅｒｒｉｎａ　ａｓｔａｕｒｏｔａ）、マメヒメサヤムシガ（Ｍａｔｓｕｍｕｒａｅｓｅｓ　ｐｈａｓｅｏｌｉ）、トビハマキ（Ｐａｎｄｅｍｉｓ　ｈｅｐａｒａｎａ）、ナシチビガ（Ｂｕｃｃｕｌａｔｒｉｘ　ｐｙｒｉｖｏｒｅｌｌａ）、モモハモグリガ（Ｌｙｏｎｅｔｉａ　ｃｌｅｒｋｅｌｌａ）、モモシンクイガ（Ｃａｒｐｏｓｉｎａ　ｎｉｐｏｎｅｎｓｉｓ）、ギンモンハモグリガ（Ｌｙｏｎｅｔｉａ　ｐｒｕｎｉｆｏｌｉｅｌｌａ　ｍａｌｉｎｅｌｌａ）、チャノホソガ（Ｃａｌｏｐｔｉｌｉａ　ｔｈｅｉｖｏｒａ）、キンモンホソガ（Ｐｈｙｌｌｏｎｏｒｙｃｔｅｒ　ｒｉｎｇｏｎｉｅｌｌａ）、ミカンハモグリガ（Ｐｈｙｌｌｏｃｎｉｓｔｉｓ　ｃｉｔｒｅｌｌａ）、ネギコガ（Ａｃｒｏｌｅｐｉｏｐｓｉｓ　ｓａｐｐｏｒｅｎｓｉｓ）、ヤマノイモコガ（Ａｃｒｏｌｅｐｉｏｐｓｉｓ　ｓｕｚｕｋｉｅｌｌａ）、コナガ（Ｐｌｕｔｅｌｌａ　ｘｙｌｏｓｔｅｌｌａ）、カキノヘタムシガ（Ｓｔａｔｈｍｏｐｏｄａ　ｍａｓｉｎｉｓｓａ）、イモキバガ（Ｈｅｌｃｙｓｔｏｇｒａｍｍａ　ｔｒｉａｎｎｕｌｅｌｌａ）、ワタアカミムシ（Ｐｅｃｔｉｎｏｐｈｏｒａ　ｇｏｓｓｙｐｉｅｌｌａ）、モモシンクイガ（Ｃａｒｐｏｓｉｎａ　ｓａｓａｋｉｉ）、ニカメイガ（Ｃｈｉｌｏ　ｓｕｐｐｒｅｓｓａｌｉｓ）、コブノメイガ（Ｃｎａｐｈａｌｏｃｒｏｃｉｓ　ｍｅｄｉｎａｌｉｓ）、チャマダラメイガ（Ｅｐｈｅｓｔｉａ　ｅｌｕｔｅｌｌａ）、モモノゴマダラノメイガ（Ｃｏｎｏｇｅｔｈｅｓ　ｐｕｎｃｔｉｆｅｒａｌｉｓ）、ワタヘリクロノメイガ（Ｄｉａｐｈａｎｉａ　ｉｎｄｉｃａ）、シロイチモジマダラメイガ（Ｅｔｉｅｌｌａ　ｚｉｎｃｋｅｎｅｌｌａ）、クワノメイガ（Ｇｌｙｐｈｏｄｅｓ　ｐｙｌｏａｌｉｓ）、イッテンオオメイガ（Ｓｃｉｒｐｏｐｈａｇａ　ｉｎｃｅｒｔｕｌａｓ）、ハイマダラノメイガ（Ｈｅｌｌｕｌａ　ｕｎｄａｌｉｓ）、アワノメイガ（Ｏｓｔｒｉｎｉａ　ｆｕｒｎａｃａｌｉｓ）、アズキノメイガ（Ｏｓｔｒｉｎｉａ　ｓｃａｐｕｌａｌｉｓ）、シバツトガ（Ｐａｒａｐｅｄｉａｓｉａ　ｔｅｔｅｒｒｅｌｌａ）、イチモンジセセリ（Ｐａｒｎａｒａ　ｇｕｔｔａｔａ）、オオモンシロチョウ（Ｐｉｅｒｉｓ　ｂｒａｓｓｉｃａｅ）、モンシロチョウ（Ｐｉｅｒｉｓ　ｒａｐａｅ　ｃｒｕｃｉｖｏｒａ）、アゲハチョウ（Ｐａｐｉｌｉｏ　ｘｕｔｈｕｓ）、ヨモギエダシャク（Ａｓｃｏｔｉｓ　ｓｅｌｅｎａｒｉａ）、ソイビーンルーパー（Ｐｓｅｕｄｏｐｌｕｓｉａ　ｉｎｃｌｕｄｅｎｓ）、チャドクガ（Ｅｕｐｒｏｃｔｉｓ　ｐｓｅｕｄｏｃｏｎｓｐｅｒｓａ）、マイマイガ（Ｌｙｍａｎｔｒｉａ　ｄｉｓｐａｒ）、ヒメシロモンドクガ（Ｏｒｇｙｉａ　ｔｈｙｅｌｌｉｎａ）、アメリカシロヒトリ（Ｈｙｐｈａｎｔｒｉａ　ｃｕｎｅａ）、クワゴマダラヒトリ（Ｌｅｍｙｒａ　ｉｍｐａｒｉｌｉｓ）、アケビコノハ（Ａｄｒｉｓ　ｔｙｒａｎｎｕｓ）、ナカジロシタバ（Ａｅｄｉａ　ｌｅｕｃｏｍｅｌａｓ）、タマナヤガ（Ａｇｒｏｔｉｓ　ｉｐｓｉｌｏｎ）、カブラヤガ（Ａｇｒｏｔｉｓ　ｓｅｇｅｔｕｍ）、タマナギンウワバ（Ａｕｔｏｇｒａｐｈａ　ｎｉｇｒｉｓｉｇｎａ）、ミツモンキンウワバ（Ｃｔｅｎｏｐｌｕｓｉａ　ａｇｎａｔａ）、コドリンガ（Ｃｙｄｌａ　ｐｏｍｏｎｅｌｌａ）、オオタバコガ（Ｈｅｌｉｃｏｖｅｒｐａ　ａｒｍｉｇｅｒａ）、タバコガ（Ｈｅｌｉｃｏｖｅｒｐａ　ａｓｓｕｌｔａ）、コットンボールワーム（Ｈｅｌｉｃｏｖｅｒｐａ　ｚｅａ）、タバコバッドワーム（Ｈｅｌｉｏｔｈｉｓ　ｖｉｒｅｓｃｅｎｓ）、ヨーロピアンコーンボーラー（Ｏｓｔｒｉｎｉａ　ｎｕｂｉｌａｌｉｓ）、ヨトウガ（Ｍａｍｅｓｔｒａ　ｂｒａｓｓｉｃａｅ）、アワヨトウ（Ｍｙｔｈｉｍｎａ　ｓｅｐａｒａｔａ）、イネヨトウ（Ｓｅｓａｍｉａ　ｉｎｆｅｒｅｎｓ）、フタオビコヤガ（Ｎａｒａｎｇａ　ａｅｎｅｓｃｅｎｓ）、サザンアーミーワーム（Ｓｐｏｄｏｐｔｅｒａ　ｅｒｉｄａｎｉａ）、シロイチモジヨトウ（Ｓｐｏｄｏｐｔｅｒａ　ｅｘｉｇｕａ）、フォールアーミーワーム（Ｓｐｏｄｏｐｔｅｒａ　ｆｒｕｇｉｐｅｒｄａ）、コットンリーフワーム（Ｓｐｏｄｏｐｔｅｒａ　ｌｉｔｔｏｒａｌｉｓ）、ハスモンヨトウ（Ｓｐｏｄｏｐｔｅｒａ　ｌｉｔｕｒａ）、スジキリヨトウ（Ｓｐｏｄｏｐｔｅｒａ　ｄｅｐｒａｖａｔａ）、イラクサギンウワバ（Ｔｒｉｃｈｏｐｌｕｓｉａ　ｎｉ）、グレープベリーモス（Ｅｎｄｏｐｉｚａ　ｖｉｔｅａｎａ）、トマトホーンワーム（Ｍａｎｄｕｃａ　ｑｕｉｎｑｕｅｍａｃｕｌａｔａ）、タバコホーンワーム（Ｍａｎｄｕｃａ　ｓｅｘｔａ）等の鱗翅目昆虫、 Specific examples of insects, mites, crustaceans, molluscs and nematodes that can be controlled using the compounds of the present invention include, for example, Adenophyes honmai and Adoxophies orana facita. , apple Mont moth (Archips breviplicanus), apple co-sink bur (Grapholita inopinata), Mi someone summer fruit moth (Archips fuscocupreanus), oriental fruit moth (Grapholita molesta), Chahamaki (Choristoneura magnanima), soybean pod borer, Leguminivora glycinivorella (Leguminivora glycinivorella), Kuwahimehamaki (Olethreutes ori), apple moth subfraction (Caloptilia zachrysa), apple Hime sink Lee (Argyresthia conjugella), Nashihosoga (Spulerrina astaurota), beans Hime Saya insect moth (Matsumuraeses phaseoli), Tobihamaki (Pandemis heparana), Nashichibiga (Bucculatrix pyrivorella), Momohamoguriga ( Lyonetia clerkella, Momoshinigaiga (Carposina niponensis), Gimmon humiligus (Lyonetia prunifoliaella marinella), Chanothosoga (Caloptilia theivora), Kinmonhosoga orycter ringoniella), mandarin orange leafminer (Phyllocnistis citrella), Negikoga (Acrolepiopsis sapporensis), yam Koga (Acrolepiopsis suzukiella), diamondback moth (Plutella xylostella), Kakinohetamushiga (Stathmopoda masinissa), Imokibaga (Helcystogramma triannulella), pink bollworm (Pectinophora gossypiella), peach fruit moth ( Carposina sasakii), Chilo suppressalis, Cnaphalocrosis medinalis, Chi Yamadarameiga (Ephestia elutella), peach Nogo Madara Roh moth (Conogethes punctiferalis), cotton helicopter Chrono moth (Diaphania indica), white-position character moth (Etiella zinckenella), Kuwanomeiga (Glyphodes pyloalis), Itten giant moth (Scirpophaga incertulas), high Madara Roh moth (Hellula undalis), Awanoaiga (Ostrinia furnacalis), Azukinoagaiga (Ostrinia scapularis), Shibatatsuga (Parapediasia teterrella), Ichimonji Seri (Parnara guttata) White butterfly (Pieris brassicae), cabbage butterfly (Pieris rapae crucivora), swallowtail butterfly (Papilio xuthus), mugwort Eda Shakti (Ascotis selenaria), soybean looper (Pseudoplusia includens), Arna Pseudoconspersa (Euproctis pseudoconspersa), gypsy moth (Lymantria dispar), orgyia thyellina (Orgyia thylina), American white-eye (Hyphantoria cunea), White-headed starfish (Lemyra imparilis), Akebiko-no-ha (Adris tyrannus), Nakajirositaba (Aedia leucomelas), Ta Nayaga (Agrotis ipsilon), Kaburayaga (Agrotis segetum), Tamanagin'uwaba (Autographa nigrisigna), honey Mont Kin looper (Ctenoplusia agnata), codling moth (Cydla pomonella), bollworm (Helicoverpa armigera), tobacco budworm (Helicoverpa assulta), cotton bollworm (Helicoverpa zea), tobacco bad worms (Heliothis virescens), European corn borers (Ostrinia nubilalis), mushrooms (Mamestra brassicae), Ayayoto (Mythina spartata) Sesamia inferens), Futaobikoyaga (Naranga aenescens), Southern armyworm (Spodoptera eridania), beet armyworm (Spodoptera exigua), fall armyworm (Spodoptera frugiperda), cotton leaf worm (Spodoptera littoralis), common cutworm (Spodoptera litura), Sujikiriyotou (Spodoptera depravata ), Nettle guava (Trichoplusia ni), grapeberry moss (Endopizza viteana), tomato horn worm (Manduca quinqueculata), tobacco horn worm (M nduca sexta) lepidopteran insects such as,
フタテンヒメヨコバイ（Ａｒｂｏｒｉｄｉａ　ａｐｉｃａｌｉｓ）、ミドリナガヨコバイ（Ｂａｌｃｌｕｔｈａ　ｓａｌｔｕｅｌｌａ）、フタテンオオヨコバイ（Ｅｐｉａｃａｎｔｈｕｓ　ｓｔｒａｍｉｎｅｕｓ）、ポテトリーフホッパー（Ｅｍｐｏａｓｃａ　ｆａｂａｅ）、カキノヒメヨコバイ（Ｅｍｐｏａｓｃａ　ｎｉｐｐｏｎｉｃａ）、チャノミドリヒメヨコバイ（Ｅｍｐｏａｓｃａ　ｏｎｕｋｉｉ）、マメノミドリヒメヨコバイ（Ｅｍｐｏａｓｃａ　ｓａｋａｉｉ）、ヒメフタテンヨコバイ（Ｍａｃｒｏｓｔｅｌｅｓ　ｓｔｒｉｉｆｒｏｎｓ）、ツマグロヨコバイ（Ｎｅｐｈｏｔｅｔｔｉｘ　ｃｉｎｃｔｉｎｃｅｐｓ）、コットンフリーホッパー（Ｐｓｕｅｄａｔｏｍｏｓｃｅｌｉｓ　ｓｅｒｉａｔｕｓ）、ヒメトビウンカ（Ｌａｏｄｅｌｐｈａｘ　ｓｔｒｉａｔｅｌｌａ）、トビイロウンカ（Ｎｉｌａｐａｒｖａｔａ　ｌｕｇｅｎｓ）、セジロウンカ（Ｓｏｇａｔｅｌｌａ　ｆｕｒｃｉｆｅｒａ）、ミカンキジラミ（Ｄｉａｐｈｏｒｉｎａ　ｃｉｔｒｉ）、ナシキジラミ（Ｐｓｙｌｌａ　ｐｙｒｉｓｕｇａ）、ミカントゲコナジラミ（Ａｌｅｕｒｏｃａｎｔｈｕｓ　ｓｐｉｎｉｆｅｒｕｓ）、シルバーリーフコナジラミ（Ｂｅｍｉｓｉａ　ａｒｇｅｎｔｉｆｏｌｉｉ）、タバココナジラミ（Ｂｅｍｉｓｉａ　ｔａｂａｃｉ）、ミカンコナジラミ（Ｄｉａｌｅｕｒｏｄｅｓ　ｃｉｔｒｉ）、オンシツコナジラミ（Ｔｒｉａｌｅｕｒｏｄｅｓ　ｖａｐｏｒａｒｉｏｒｕｍ）、ブドウコナジラミ（Ａｌｅｕｒｏｌｏｂｕｓ　ｔａｏｎａｂａｅ）、ブドウネアブラムシ（Ｖｉｔｅｕｓ　ｖｉｔｉｆｏｌｉｉ）、ニセダイコンアブラムシ（Ｌｉｐａｐｈｉｓ　ｅｒｙｓｉｍｉ）、ワタアブラムシ（Ａｐｈｉｓ　ｇｏｓｓｙｐｉｉ）、ユキヤナギアブラムシ（Ａｐｈｉｓ　ｓｐｉｒａｅｃｏｌａ）、モモアカアブラムシ（Ｍｙｚｕｓ　ｐｅｒｓｉｃａｅ）、コミカンアブラムシ（Ｔｏｘｏｐｔｅｒａ　ａｕｒａｎｔｉｉ）、オオワラジカイガラムシ（Ｄｒｏｓｉｃｈａ　ｃｏｒｐｕｌｅｎｔａ）、イセリアカイガラムシ（Ｉｃｅｒｙａ　ｐｕｒｃｈａｓｉ）、ナスコナカイガラムシ（Ｐｈｅｎａｃｏｃｃｕｓ　ｓｏｌａｎｉ）、ミカンワタカイガラムシ（Ｐｕｌｖｉｎａｒｉａ　ａｕｒａｎｔｉｉ）、ミカンコナカイガラムシ（Ｐｌａｎｏｃｏｃｃｕｓ　ｃｉｔｒｉ）、ミカンマルカイガラムシ（Ｐｓｅｕｄａｏｎｉｄｉａ　ｄｕｐｌｅｘ）、フジコナカイガラムシ（Ｐｌａｎｏｃｏｃｃｕｓ　ｋｕｒａｕｎｈｉａｅ）、クワコナカイガラムシ（Ｐｓｅｕｄｏｃｏｃｃｕｓ　ｃｏｍｓｔｏｃｋｉ）、ナシマルカイガラムシ（Ｃｏｍｓｔｏｃｋａｓｐｉｓ　ｐｅｒｎｉｃｉｏｓａ）、ツノロウムシ（Ｃｅｒｏｐｌａｓｔｅｓ　ｃｅｒｉｆｅｒｕｓ）、ルビーロウムシ（Ｃｅｒｏｐｌａｓｔｅｓ　ｒｕｂｅｎｓ）、アカマルカイガラムシ（Ａｏｎｉｄｉｅｌｌａ　ａｕｒａｎｔｉｉ）、ティースケール（Ｆｉｏｒｉｎｉａ　ｔｈｅａｅ）、チャノマルカイガラムシ（Ｐｓｅｕｄａｏｎｉｄｉａ　ｐａｅｏｎｉａｅ）、クワシロカイガラムシ（Ｐｓｅｕｄａｕｌａｃａｓｐｉｓ　ｐｅｎｔａｇｏｎａ）、ウメシロカイガラムシ（Ｐｓｅｕｄａｕｌａｃａｓｐｉｓ　ｐｒｕｎｉｃｏｌａ）、マサキナガカイガラムシ（Ｕｎａｓｐｉｓ　ｅｕｏｎｙｍｉ）、ヤノネカイガラムシ（Ｕｎａｓｐｉｓ　ｙａｎｏｎｅｎｓｉｓ）、トコジラミ（Ｃｉｍｅｘ　ｌｅｃｔｕｌａｒｉｕｓ）、ブチヒゲカメムシ（Ｄｏｌｙｃｏｒｉｓ　ｂａｃｃａｒｕｍ）、ナガメ（Ｅｕｒｙｄｅｍａ　ｒｕｇｏｓｕｍ）、トゲシラホシカメムシ（Ｅｙｓａｒｃｏｒｉｓ　ａｅｎｅｕｓ）、オオトゲシラホシカメムシ（Ｅｙｓａｒｃｏｒｉｓ　ｌｅｗｉｓｉ）、シラホシカメムシ（Ｅｙｓａｒｃｏｒｉｓ　ｖｅｎｔｒａｌｉｓ）、ツヤアオカメムシ（Ｇｌａｕｃｉａｓ　ｓｕｂｐｕｎｃｔａｔｕｓ）、クサギカメムシ（Ｈａｌｙｏｍｏｒｐｈａ　ｈａｌｙｓ）、アオクサカメムシ（Ｎｅｚａｒａ　ａｎｔｅｎｎａｔａ）、ミナミアオカメムシ（Ｎｅｚａｒａ　ｖｉｒｉｄｕｌａ）、イチモンジカメムシ（Ｐｉｅｚｏｄｏｒｕｓ　ｈｙｂｎｅｒｉ）、チャバネアオカメムシ（Ｐｌａｕｔｉａ　ｃｒｏｓｓｏｔａ）、イネクロカメムシ（Ｓｃｏｔｉｎｏｐｈｏｒａ　ｌｕｒｉｄａ）、ホソハリカメムシ（Ｃｌｅｔｕｓ　ｐｕｎｃｔｉｇｅｒ）、クモヘリカメムシ（Ｌｅｐｔｏｃｏｒｉｓａ　ｃｈｉｎｅｎｓｉｓ）、ホソヘリカメムシ（Ｒｉｐｔｏｒｔｕｓ　ｃｌａｖａｔｕｓ）、アカヒメヘリカメムシ（Ｒｈｏｐａｌｕｓ　ｍｓｃｕｌａｔｕｓ）、カンシャコバネナガカメムシ（Ｃａｖｅｌｅｒｉｕｓ　ｓａｃｃｈａｒｉｖｏｒｕｓ）、コバネヒョウタンナガカメムシ（Ｔｏｇｏ　ｈｅｍｉｐｔｅｒｕｓ）、アカホシカメムシ（Ｄｙｓｄｅｒｃｕｓ　ｃｉｎｇｕｌａｔｕｓ）、ツツジグンバイ（Ｓｔｅｐｈａｎｉｔｉｓ　ｐｙｒｉｏｉｄｅｓ）、クロトビカスミカメ（Ｈａｌｔｉｃｕｓ　ｉｎｓｕｌａｒｉｓ）、ターニッシュドプラントバグ（Ｌｙｇｕｓ　ｌｉｎｅｏｌａｒｉｓ）、ナガムギカスミカメ（Ｓｔｅｎｏｄｅｍａ　ｓｉｂｉｒｉｃｕｍ）、アカスジカスミカメ（Ｓｔｅｎｏｔｕｓ　ｒｕｂｒｏｖｉｔｔａｔｕｓ）、イネホソミドリカスミカメ（Ｔｒｉｇｏｎｏｔｙｌｕｓ　ｃａｅｌｅｓｔｉａｌｉｕｍ）等の半翅目昆虫、 Pepper leaf beetle (Arboridia apicalis), Green leafhopper (Balcrutha saltuella), Pepper leaf beetle (Epicaanthus stamineus), Potato leaf abalone (Empoasca pea) , Peanut leafhopper (Empoasaka sakaii), leafhopper leafhopper (Macrosteles striifrons), leafhopper leafhopper (Nephotettix cincinceps), cotton-free hopper (Psuedatomososerissera tossera tossera serisser seraistosera serissertosera tossera serasto elphax striatella), brown planthopper (Nilaparvata lugens), Sejirounka (Sogatella furcifera), Diaphorina citri (Diaphorina citri), Nashikijirami (Psylla pyrisuga), mandarin orange spiny whitefly (Aleurocanthus spiniferus), silverleaf whitefly (Bemisia argentifolii), tobacco whitefly (Bemisia tabaci) , Citrus whitefly (Dialeurodes citri), white lice (Trialeurodes vaporiarum), white lice (Aleurobus taonabae), vine aphids (Vite) svitifolii, Aphid erysimi, Cotton aphid (Aphis spiraecola), Aphis terrica terridium, Aphis sapia tera Iceria scales (Icerya purchasi), Phytococcus solani, citrus scales (Pulvinaria aurantii), citrus scales (Pranococcus citri), Peanococcus citridon duplex), mealybug (Planococcus kuraunhiae), mulberry mealybugs (Pseudococcus comstocki), no circle scale insects (Comstockaspis perniciosa), Tsunoroumushi (Ceroplastes ceriferus), Rubiroumushi (Ceroplastes rubens), Acamar scale insects (Aonidiella aurantii), tea scale (Fiorinia theae, Pseudaondia paeoniae, Pseudouracapis pentagona, Pseudaulacapsis prun cola), Japanese hornworm scale (Unaspis euonymi), Wildflower scale pod (Unaspis yanonensis), Japanese hornet worm (Cirex electorius), Spotted beetle (Dolicoris baccarum), Nyme moth Stink bug (Eysarcoris lewisi), Shirahoshi stink bug (Eysarcoris ventralis), Tsutsuaokamemushi (Glaucias subfunctus), Rabbit beetle (Halyomorpha halis) ara viridula), beet bug (Piezodorus hybneri), Plautia crossota green bug (Plautia crossota), rice black bug (Scotinophora lurida), bombardier Hari bug (Cletus punctiger), spider helicopter bug (Leptocorisa chinensis), bombardier helicopter stink bug (Riptortus clavatus) , Red-spotted beetle (Rhopalus musculatus), red-footed beetle (Caverelius saccharivorus), red-headed beetle (Togo hemipterus), red-spotted beetle (Dysdercous) Stephanitis pyrioides, Halticus insularis, Tarnished plant bugs (Lygus linearolais), Nugget swordfish (Stenodema sibilicum), Stemisosomitusi turtles Eye insect,
ドウガネブイブイ（Ａｎｏｍａｌａ　ｃｕｐｒｅａ）、ヒメコガネ（Ａｎｏｍａｌａ　ｒｕｆｏｃｕｐｒｅａ）、コアオハナムグリ（Ｇａｍｅｔｉｓ　ｊｕｃｕｎｄａ）、ナガチャコガネ（Ｈｅｐｔｏｐｈｙｌｌａ　ｐｉｃｅａ）、マメコガネ（Ｐｏｐｉｌｌｉａ　ｊａｐｏｎｉｃａ）、コロラドポテトビートル（Ｌｅｐｉｎｏｔａｒｓａ　ｄｅｃｅｍｌｉｎｅａｔａ）、メキシカンビートビートル（Ｅｐｉｌａｃｈｎａ　ｖａｒｉｖｅｓｔｉｓ）、マルクビクシコメツキ（Ｍｅｌａｎｏｔｕｓ　ｆｏｒｔｎｕｍｉ）、カンシャクシコメツキ（Ｍｅｌａｎｏｔｕｓ　ｔａｍｓｕｙｅｎｓｉｓ）、タバコシバンムシ（Ｌａｓｉｏｄｅｒｍａ　ｓｅｒｒｉｃｏｒｎｅ）、ヒラタキクイムシ（Ｌｙｃｔｕｓｂｒｕｎｎｅｕｓ）、マツノキクイムシ（Ｔｏｍｉｃｕｓ　ｐｉｎｉｐｅｒｄａ）、ナガシンクイムシ（Ｒｈｉｚｏｐｅｒｔｈａ　ｄｏｍｉｎｉｃａ）、ヒメヒラタケシキスイ（Ｅｐｕｒａｅａ　ｄｏｍｉｎａ）、インゲンテントウ（Ｅｐｉｌａｃｈｎａ　ｖａｒｉｖｅｓｔｉｓ）、ニジュウヤホシテントウ（Ｅｐｉｌａｃｈｎａ　ｖｉｇｉｎｔｉｏｃｔｏｐｕｎｃｔａｔａ）、チャイロコメノゴミムシダマシ（Ｔｅｎｅｂｒｉｏ　ｍｏｌｉｔｏｒ）、コクヌストモドキ（Ｔｒｉｂｏｌｉｕｍ　ｃａｓｔａｎｅｕｍ）、ゴマダラカミキリ（Ａｎｏｐｌｏｐｈｏｒａ　ｍａｌａｓｉａｃａ）、マツノマダラカミキリ（Ｍｏｎｏｃｈａｍｕｓ　ａｌｔｅｒｎａｔｕｓ）、キボシカミキリ（Ｐｓａｃｏｔｈｅａ　ｈｉｌａｒｉｓ）、ブドウトラカミキリ（Ｘｙｌｏｔｒｅｃｈｕｓ　ｐｙｒｒｈｏｄｅｒｕｓ）、アズキゾウムシ（Ｃａｌｌｏｓｏｂｒｕｃｈｕｓ　ｃｈｉｎｅｎｓｉｓ）、ウリハムシ（Ａｕｌａｃｏｐｈｏｒａ　ｆｅｍｏｒａｌｉｓ）、イネドロオイムシ（Ｏｕｌｅｍａ　ｏｒｙｚａｅ）、テンサイトビハムシ（Ｃｈａｅｔｏｃｎｅｍａ　ｃｏｎｃｉｎｎａ）、サザンコーンルートワーム（Ｄｉａｂｒｏｔｉｃａ　ｕｎｄｅｃｉｍｐｕｎｃｔａｔａ）、ウエスタンコーンルートワーム（Ｄｉａｂｒｏｔｉｃａ　ｖｉｒｇｉｆｅｒａ）、ノーザンコーンルートワーム（Ｄｉａｂｒｏｔｉｃａ　ｂａｒｂｅｒｉ）、キスジノミハムシ（Ｐｈｙｌｌｏｔｒｅｔａ　ｓｔｒｉｏｌａｔａ）、ナスナガスネトビハムシ（Ｐｓｙｌｌｉｏｄｅｓ　ａｎｇｕｓｔｉｃｏｌｌｉｓ）、モモチョッキリゾウムシ（Ｒｈｙｎｃｈｉｔｅｓ　ｈｅｒｏｓ）、アリモドキゾウムシ（Ｃｙｌａｓ　ｆｏｒｍｉｃａｒｉｕｓ）、ワタミゾウムシ（Ａｎｔｈｏｎｏｍｕｓ　ｇｒａｎｄｉｓ）、イネゾウムシ（Ｅｃｈｉｎｏｃｎｅｍｕｓ　ｓｑｕａｍｅｕｓ）、イモゾウムシ（Ｅｕｓｃｅｐｅｓ　ｐｏｓｔｆａｓｃｉａｔｕｓ）、アルファルファタコゾウムシ（Ｈｙｐｅｒａ　ｐｏｓｔｉｃａ）、イネミズゾウムシ（Ｌｉｓｓｏｈｏｐｔｒｕｓ　ｏｒｙｚｏｐｈｉｌｕｓ）、キンケクチブトゾウムシ（Ｏｔｉｏｒｈｙｎｃｈｕｓ　ｓｕｌｃａｔｕｓ）、グラナリーウィービル（Ｓｉｔｏｐｈｉｌｕｓ　ｇｒａｎａｒｉｕｓ）、コクゾウムシ（Ｓｉｔｏｐｈｉｌｕｓ　ｚｅａｍａｉｓ）、シバオサゾウムシ（Ｓｐｈｅｎｏｐｈｏｒｕｓ　ｖｅｎａｔｕｓ　ｖｅｓｔｉｔｕｓ）、アオバアリガタハネカクシ（Ｐａｅｄｅｒｕｓ　ｆｕｓｃｉｐｅｓ）等の鞘翅目昆虫、 Cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), core Oh flower chafer (Gametis jucunda), Nagachakogane (Heptophylla picea), Japanese beetle (Popillia japonica), Colorado potato beetle (Lepinotarsa decemlineata), Mexican beat beetle (Epilachna varivestis), crew neck Melanotus fortumi, Melanus tamsuyensis, Tobacco beetle (Lasiderma serricorne), Japanese horned beetle (Lyctusbrunneus), Matsukikushi omicus piniperda), Naga Shinkuimushi (Rhizopertha dominica), Hime Hirata Keshikisui (Epuraea domina), bean beetle (Epilachna varivestis), the beetle, Epilachna vigintioctopunctata (Epilachna vigintioctopunctata), Chai Loco Meno mealworm (Tenebrio molitor), red flour beetle (Tribolium castaneum) , Japanese spotted beetle (Anoprophora malasiaca), Japanese pine beetle (Monochamus alternatus), Japanese red beetle (Psacothea hilaris), Grape tiger beetle (Xylotrechus pyrrr) oderus), adzuki bean weevil (Callosobruchus chinensis), cucurbit leaf beetle (Aulacophora femoralis), Inedorooimushi (Oulema oryzae), Ten site bi potato beetle (Chaetocnema concinna), Southern corn rootworm (Diabrotica undecimpunctata), Western corn rootworm (Diabrotica virgifera), Northern Corn root worms (Diabrotica barberi), kisslet flea beetle (Phyllotreta sriolata), nasal beetle (Psyllodes angusticollilis), peach beetle weevil (Rhynchites h) eros), sweet potato weevil (Cylas formicarius), boll weevil (Anthonomus grandis), rice weevil (Echinocnemus squameus), Imozoumushi (Euscepes postfasciatus), alfalfa weevil (Hypera postica), rice water weevil (Lissohoptrus oryzophilus), Kin Ke vine but-weevil (Otiorhynchus sulcatus ), Granary Weeville (Sitophilus granarius), Blossom Weevil (Sitophilus zeamais), Weevil Weevil (Sphenophorus venatus vestitus), Aobaarigatahane Coleoptera insect, such as a comb (Paederus fuscipes),
ヒラズハナアザミウマ（Ｆｒａｎｋｌｉｎｉｅｌｌａ　ｉｎｔｏｎｓａ）、キイロハナアザミウマ（Ｔｈｒｉｐｓ　ｆｌａｖｕｓ）、ミカンキイロアザミウマ（Ｆｒａｎｋｌｉｎｉｅｌｌａ　ｏｃｃｉｄｅｎｔａｌｉｓ）、クロトンアザミウマ（Ｈｅｌｉｏｔｈｒｉｐｓ　ｈａｅｍｏｒｒｈｏｉｄａｌｉｓ）、チャノキイロアザミウマ（Ｓｃｉｒｔｏｔｈｒｉｐｓ　ｄｏｒｓａｌｉｓ）、ミナミキイロアザミウマ（Ｔｈｒｉｐｓ　ｐａｌｍｉ）、ネギアザミウマ（Ｔｈｒｉｐｓ　ｔａｂａｃｉ）、カキクダアザミウマ（Ｐｏｎｔｉｃｕｌｏｔｈｒｉｐｓ　ｄｉｏｓｐｙｒｏｓｉ）、等の総翅目昆虫、 Hirazuhanaazamiuma (Frankliniella intonsa), Yellow Hana thrips (Thrips flavus), western flower thrips (Frankliniella occidentalis), Croton thrips (Heliothrips haemorrhoidalis), yellow tea thrips (Scirtothrips dorsalis), southern thrips (Thrips palmi), green onion thrips (Thrips tabaci ), Coleoptera thrips (Ponticulotrips diospyrosi), etc.
ダイズサヤタマバエ（Ａｓｐｈｏｎｄｙｌｉａ　ｙｕｓｈｉｍａｉ）、ムギアカタマバエ（Ｓｉｔｏｄｉｐｌｏｓｉｓ　ｍｏｓｅｌｌａｎａ）、ウリミバエ（Ｂａｃｔｒｏｃｅｒａ　ｃｕｃｕｒｂｉｔａｅ）、ミカンコミバエ（Ｂａｃｔｒｏｃｅｒａ　ｄｏｒｓａｌｉｓ）、チチュウカイミバエ（Ｃｅｒａｔｉｔｉｓ　ｃａｐｉｔａｔａ）、イネヒメハモグリバエ（Ｈｙｄｒｅｌｌｉａ　ｇｒｉｓｅｏｌａ）、オウトウショウジョウバエ（Ｄｒｏｓｏｐｈｉｌａ　ｓｕｚｕｋｉｉ）、イネハモグリバエ（Ａｇｒｏｍｙｚａ　ｏｒｙｚａｅ）、ナモグリバエ（Ｃｈｒｏｍａｔｏｍｙｉａ　ｈｏｒｔｉｃｏｌａ）、ナスハモグリバエ（Ｌｉｒｉｏｍｙｚａ　ｂｒｙｏｎｉａｅ）、ネギハモグリバエ（Ｌｉｒｉｏｍｙｚａ　ｃｈｉｎｅｎｓｉｓ）、トマトハモグリバエ（Ｌｉｒｉｏｍｙｚａ　ｓａｔｉｖａｅ）、マメハモグリバエ（Ｌｉｒｉｏｍｙｚａ　ｔｒｉｆｏｌｉｉ）、タネバエ（Ｄｅｌｉａ　ｐｌａｔｕｒａ）、タマネギバエ（Ｄｅｌｉａ　ａｎｔｉｑｕｅ）、テンサイモグリハナバエ（Ｐｅｇｏｍｙａ　ｃｕｎｉｃｕｌａｒｉａ）、アップルマゴット（Ｒｈａｇｏｌｅｔｉｓ　ｐｏｍｏｎｅｌｌａ）、ヘシアンフライ（Ｍａｙｅｔｉｏｌａ　ｄｅｓｔｒｕｃｔｏｒ）、イエバエ（Ｍｕｓｃａ　ｄｏｍｅｓｔｉｃａ）、サシバエ（Ｓｔｏｍｏｘｙｓ　ｃａｌｃｉｔｒａｎｓ）、ヒツジシラミバエ（Ｍｅｌｏｐｈａｇｕｓ　ｏｖｉｎｕｓ）、ウシバエ（Ｈｙｐｏｄｅｒｍａ　ｂｏｖｉｓ）、キスジウシバエ（Ｈｙｐｏｄｅｒｍａ　ｌｉｎｅａｔｕｍ）、ヒツジバエ（Ｏｅｓｔｒｕｓ　ｏｖｉｓ）、ツェツェバエ（Ｇｌｏｓｓｉｎａ　ｐａｌｐａｌｉｓ，　Ｇｌｏｓｓｉｎａ　ｍｏｒｓｉｔａｎｓ）、キアシオオブユ（Ｐｒｏｓｉｍｕｌｉｕｍ　ｙｅｚｏｅｎｓｉｓ）、ウシアブ（Ｔａｂａｎｕｓ　ｔｒｉｇｏｎｕｓ）、オオチョウバエ（Ｔｅｌｍａｔｏｓｃｏｐｕｓ　ａｌｂｉｐｕｎｃｔａｔｕｓ）、トクナガヌカカ（Ｌｅｐｔｏｃｏｎｏｐｓ　ｎｉｐｐｏｎｅｎｓｉｓ）、アカイエカ（Ｃｕｌｅｘ　ｐｉｐｉｅｎｓ　ｐａｌｌｅｎｓ）、ネッタイシマカ（Ａｅｄｅｓ　ａｅｇｙｐｔｉ）、ヒトスジシマカ（Ａｅｄｅｓ　ａｌｂｏｐｉｃｕｔｕｓ）、シナハマダラカ（Ａｎｏｐｈｅｌｅｓ　ｈｙｒａｃａｎｕｓ　ｓｉｎｅｓｉｓ）等の双翅目昆虫、 Soybean pod gall midge (Asphondylia yushimai), wheat red gall midge (Sitodiplosis mosellana), melon fly (Bactrocera cucurbitae), oriental fruit fly (Bactrocera dorsalis), the Mediterranean fruit fly (Ceratitis capitata), rice Hime leafminer (Hydrellia griseola), cherry fruit fly (Drosophila suzukii), rice Leafhopper (Agromyza oryzae), leafworm (Chromatomia horticola), eggplant leaffly (Liriomyza bryoniae), leafhopper (Liriomyza chinensis), Mato leafminer (Liriomyza sativae), legume leafminer (Liriomyza trifolii), seedcorn maggot (Delia platura), onion maggot (Delia antique), sugar beet diving Hana fly (Pegomya cunicularia), Apple Maggot (Rhagoletis pomonella), Heshianfurai (Mayetiola destructor), housefly (Musca domestica), flies (Stomoxys calcitrans), sheep flies (Melophagus ovinus), bullflies (Hypoderma bovis), Hypotherma lineaeum (Hypodermalinetrus) ovis), tsetse flies (Glossina palpalis, Glossina morsitans), Kiashioobuyu (Prosimulium yezoensis), gadfly (Tabanus trigonus), giant flies (Telmatoscopus albipunctatus), Tokunaganukaka (Leptoconops nipponensis), mosquito (Culex pipiens pallens), Aedes aegypti (Aedes aegypti), Diptera insects such as Aedes albopicutus, Anopheles hyracanus synthesis,
クリハバチ（Ａｐｅｔｈｙｍｕｓ　ｋｕｒｉ）、カブラハバチ（Ａｔｈａｌｉａ　ｒｏｓａｅ）、チュウレンジハバチ（Ａｒｇｅ　ｐａｇａｎａ）、マツノキハバチ（Ｎｅｏｄｉｐｒｉｏｎ　ｓｅｒｔｉｆｅｒ）、クリタマバチ（Ｄｒｙｏｃｏｓｍｕｓ　ｋｕｒｉｐｈｉｌｕｓ）、グンタイアリ（Ｅｃｉｔｏｎ　ｂｕｒｃｈｅｌｌｉ，　Ｅｃｉｔｏｎ　ｓｃｈｍｉｔｔｉ）、クロオオアリ（Ｃａｍｐｏｎｏｔｕｓ　ｊａｐｏｎｉｃｕｓ）、オオスズメバチ（Ｖｅｓｐａ　ｍａｎｄａｒｉｎａ）、ブルドックアント（Ｍｙｒｍｅｃｉａ　ｓｐｐ．）、ファイヤーアント類（Ｓｏｌｅｎｏｐｓｉｓ　ｓｐｐ．）、ファラオアント（Ｍｏｎｏｍｏｒｉｕｍ　ｐｈａｒａｏｎｉｓ）等の膜翅目昆虫、 Kurihabachi (Apethymus kuri), Kaburahabachi (Athalia rosae), Chu range sawfly (Arge pagana), Matsunokihabachi (Neodiprion sertifer), Kuritamabachi (Dryocosmus kuriphilus), army ant (Eciton burchelli, Eciton schmitti), Camponotus japonicus (Camponotus japonicus), Asian giant hornet (Vespa mandarina, bulldog ant (Myrmecia spp.), fire ant (Solenopsis spp.), pharaoh ant (Monomomorium pharaonis), etc.
エンマコオロギ（Ｔｅｌｅｏｇｒｙｌｌｕｓ　ｅｍｍａ）、ケラ（Ｇｒｙｌｌｏｔａｌｐａ　ｏｒｉｅｎｔａｌｉｓ）、トノサマバッタ（Ｌｏｃｕｓｔａ　ｍｉｇｒａｔｏｒｉａ）、コバネイナゴ（Ｏｘｙａ　ｙｅｚｏｅｎｓｉｓ）、サバクワタリバッタ（Ｓｃｈｉｓｔｏｃｅｒｃａ　ｇｒｅｇａｒｉａ）等の直翅目昆虫、 Emma crickets (Teleoglyllus emma), Kera (Gryllotalpa orientalis), Tosama grasshopper (Locusta migratoria), Oba yezoensis, etc.
トゲナシシロトビムシ（Ｏｎｙｃｈｉｕｒｕｓ　ｆｏｌｓｏｍｉ）、シベリアシロトビムシ（Ｏｎｙｃｈｉｕｒｕｓ　ｓｉｂｉｒｉｃｕｓ）、キボシマルトビムシ（Ｂｏｕｒｌｅｔｉｅｌｌａ　ｈｏｒｔｅｎｓｉｓ）等の粘管目昆虫、 Coleopterous insects such as the white-headed beetle (Onychiurus folsomi), the siberian white-headed beetle (Onychiurus sibiricus), and the burdock beetle (Bourletiella hortensis),
クロゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ　ｆｕｌｉｇｉｎｏｓａ）、ヤマトゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ　ｊａｐｏｎｉｃａ）、チャバネゴキブリ（Ｂｌａｔｔｅｌｌａ　ｇｅｒｍａｎｉｃａ）、ワモンゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ　Ａｍｅｒｉｃａｎａ）、等の網翅目昆虫、 Black-eye cockroach (Periplaneta fuliginosa), Japanese cockroach (Periplaneta japonica), German cockroach (Blattella germanica), American cockroach (Periplaneta americana), etc.
イエシロアリ（Ｃｏｐｔｏｔｅｒｍｅｓ　ｆｏｒｍｏｓａｎｕｓ）、ヤマトシロアリ（Ｒｅｔｉｃｕｌｉｔｅｒｍｅｓ　ｓｐｅｒａｔｕｓ）、タイワンシロアリ（Ｏｄｏｎｔｏｔｅｒｍｅｓ　ｆｏｒｍｏｓａｎｕｓ）等のシロアリ目昆虫、 Termite insects such as termites (Coptothermes formosanus), Yamato termites (Reticulitermes supertus), Taiwan termites (Odontotermes formosanus),
ネコノミ（Ｃｔｅｎｏｃｅｐｈａｌｉｄａｅ　ｆｅｌｉｓ）、イヌノミ（Ｃｔｅｎｏｃｅｐｈａｌｉｄｅｓ　ｃａｎｉｓ）、ニワトリノミ（Ｅｃｈｉｄｎｏｐｈａｇａ　ｇａｌｌｉｎａｃｅａ）、ヒトノミ（Ｐｕｌｅｘ　ｉｒｒｉｔａｎｓ）、ケオプスネズミノミ（Ｘｅｎｏｐｓｙｌｌａ　ｃｈｅｏｐｉｓ）等の等翅目昆虫、 Cat fleas (Ctenocephalidae felis), dog fleas (Ctenocephalides canis), chicken fleas (Echidnophaga gallinacea), human fleas (Pulex iriritans), insects of the mosquito, etc.
ニワトリオオハジラミ（Ｍｅｎａｃａｎｔｈｕｓ　ｓｔｒａｍｉｎｅｕｓ）、ウシハジラミ（Ｂｏｖｉｃｏｌａ　ｂｏｖｉｓ）等のハジラミ目昆虫、 Insects such as chicken lice (Mecananthus stramineus), bovine lice (Bovicola bovis),
ウシジラミ（Ｈａｅｍａｔｏｐｉｎｕｓ　ｅｕｒｙｓｔｅｒｎｕｓ）、ブタジラミ（Ｈａｅｍａｔｏｐｉｎｕｓ　ｓｕｉｓ）、ウシホソジラミ（Ｌｉｎｏｇｎａｔｈｕｓ　ｖｉｔｕｌｉ）、ケブカウシジラミ（Ｓｏｌｅｎｏｐｏｔｅｓ　ｃａｐｉｌｌａｔｕｓ）等のシラミ目昆虫、 Lice insects such as cattle lice (Haematopinus eurysternus), pig lice (Haematopinus suis), cattle white lice (Linognathus vituli), kelp cause lice (Solenopotes capillatus), etc.
シクラメンホコリダニ（Ｐｈｙｔｏｎｅｍｕｓ　ｐａｌｌｉｄｕｓ）、チャノホコリダニ（Ｐｏｌｙｐｈａｇｏｔａｒｓｏｎｅｍｕｓ　ｌａｔｕｓ）、スジブトホコリダニ（Ｔａｒｓｏｎｅｍｕｓ　ｂｉｌｏｂａｔｕｓ）等のホコリダニ類、
ハクサイダニ（Ｐｅｎｔｈａｌｅｕｓ　ｅｒｙｔｈｒｏｃｅｐｈａｌｕｓ）、ムギダニ（Ｐｅｎｔｈａｌｅｕｓ　ｍａｊｏｒ）等のハシリダニ類、
イネハダニ（Ｏｌｉｇｏｎｙｃｈｕｓ　ｓｈｉｎｋａｊｉｉ）、ミカンハダニ（Ｐａｎｏｎｙｃｈｕｓ　ｃｉｔｒｉ）、クワオオハダニ（Ｐａｎｏｎｙｃｈｕｓ　ｍｏｒｉ）、リンゴハダニ（Ｐａｎｏｎｙｃｈｕｓ　ｕｌｍｉ）、カンザワハダニ（Ｔｅｔｒａｎｙｃｈｕｓ　ｋａｎｚａｗａｉ）、ナミハダニ（Ｔｅｔｒａｎｙｃｈｕｓ　ｕｒｔｉｃａｅ）等のハダニ類、
チャノナガサビダニ（Ａｃａｐｈｙｌｌａ　ｔｈｅａｖａｇｒａｎｓ）、チューリップサビダニ（Ａｃｅｒｉａ　ｔｕｌｉｐａｅ）、トマトサビダニ（Ａｃｕｌｏｐｓ　ｌｙｃｏｐｅｒｓｉｃｉ）、ミカンサビダニ（Ａｃｕｌｏｐｓ　ｐｅｌｅｋａｓｓｉ）、リンゴサビダニ（Ａｃｕｌｕｓ　ｓｃｈｌｅｃｈｔｅｎｄａｌｉ）、ニセナシサビダニ（Ｅｒｉｏｐｈｙｅｓ　ｃｈｉｂａｅｎｓｉｓ）、シトラスラストマイト（Ｐｈｙｌｌｏｃｏｐｔｒｕｔａ　ｏｌｅｉｖｏｒａ）等のフシダニ類、
ロビンネダニ（Ｒｈｉｚｏｇｌｙｐｈｕｓ　ｒｏｂｉｎｉ）、ケナガコナダニ（Ｔｙｒｏｐｈａｇｕｓ　ｐｕｔｒｅｓｃｅｎｔｉａｅ）、ホウレンソウケナガコナダニ（Ｔｙｒｏｐｈａｇｕｓ　ｓｉｍｉｌｉｓ）等のコナダニ類、
ミツバチヘギイタダニ（Ｖａｒｒｏａ　ｊａｃｏｂｓｏｎｉ）等のハチダニ類、
オウシマダニ（Ｂｏｏｐｈｉｌｕｓ　ｍｉｃｒｏｐｌｕｓ）、クリイロコイタマダニ（Ｒｈｉｐｉｃｅｐｈａｌｕｓ　ｓａｎｇｕｉｎｅｕｓ）、フタトゲチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ　ｌｏｎｇｉｃｏｒｎｉｓ）、キチマダニ（Ｈａｅｍｏｐｈｙｓａｌｉｓ　ｆｌａｖａ）、ツリガネチマダニ（Ｈａｅｍｏｐｈｙｓａｌｉｓ　ｃａｍｐａｎｕｌａｔａ）、ヤマトチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ　ｊａｐｏｎｉｃａ）、オオトゲチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ　ｍｅｇａｓｐｉｎｏｓａ）、ヤマトマダニ（Ｉｘｏｄｅｓ　ｏｖａｔｕｓ）、シュルツェマダニ（Ｉｘｏｄｅｓ　ｐｅｒｓｕｌｃａｔｕｓ）、タネガタマダニ（Ｉｘｏｄｅｓ　ｎｉｐｐｏｎｅｎｓｉｓ）、西部クロアシダニ（Ｉｘｏｄｅｓ　ｐａｃｉｆｃｕｓ）、ヒツジダニ（Ｉｘｏｄｅｓ　ｒｉｃｉｎｕｓ）、クロアシダニ（Ｉｘｏｄｅｓ　ｓｃａｐｕｌａｒｉｓ）、ローン・スターマダニ（Ａｍｂｌｙｏｍｍａ　ａｍｅｒｉｃａｎｕｍ）、メキシコ湾岸マダニ（Ａｍｂｌｙｏｍｍａ　ｍａｃｕｌａｔｕｍ）、オオマダニ（Ａｍｂｌｙｏｍｍａ　ｓｐｐ．）、アミメカクマダニ（Ｄｅｒｍａｃｅｎｔｏｒ　ｒｅｃｔｉｃｕｌａｔｕｓ）、タイワンカクマダニ（Ｄｅｒｍａｃｅｎｔｏｒ　ｔａｉｗａｎｅｎｓｉｓ）、ロッキー山脈森林マダニ（Ｄｅｒｍａｃｅｎｔｏｒ　ａｎｄｅｒｓｏｎｉ）、西海岸マダニ（Ｄｅｒｍａｃｅｎｔｏｒ　ｏｃｃｉｄｅｎｔａｌｉｓ）、アメリカンドッグティック（Ｄｅｒｍａｃｅｎｔｏｒ　ｖａｒｉａｂｉｌｉｓ）、アミメマダニ（Ｄｅｒｍａｃｅｎｔｏｒ　ｓｐｐ．）等のマダニ類、
イヌツメダニ（Ｃｈｅｙｌｅｔｉｅｌｌａ　ｙａｓｇｕｒｉ）、ネコツメダニ（Ｃｈｅｙｌｅｔｉｅｌｌａ　ｂｌａｋｅｉ）等のツメダニ類、
イヌニキビダニ（Ｄｅｍｏｄｅｘ　ｃａｎｉｓ）、ネコニキビダニ（Ｄｅｍｏｄｅｘ　ｃａｔｉ）などのニキビダニ類、
ヒツジキュウセンダニ（Ｐｓｏｒｏｐｔｅｓ　ｏｖｉｓ）等のキュウセンダニ類、
センコウヒゼンダニ（Ｓａｒｃｏｐｔｅｓ　ｓｃａｂｉｅｉ）、ネコショウセンコウヒゼンダニ（Ｎｏｔｏｅｄｒｅｓ　ｃａｔｉ）、ニワトリヒゼンダニ（Ｋｎｅｍｉｄｏｃｏｐｔｅｓ　ｓｐｐ．）等のヒゼンダニ類、
オカダンゴムシ（Ａｒｍａｄｉｌｌｉｄｉｕｍ　ｖｕｌｇａｒｅ）等の甲殻類、
スクミリンゴガイ（Ｐｏｍａｃｅａ　ｃａｎａｌｉｃｕｌａｔａ）、アフリカマイマイ（Ａｃｈａｔｉｎａ　ｆｕｌｉｃａ）、ナメクジ（Ｍｅｇｈｉｍａｔｉｕｍ　ｂｉｌｉｎｅａｔｕｍ）、チャコウラナメクジ（Ｌｉｍａｘ　Ｖａｌｅｎｔｉａｎａ）、ウスカワマイマイ（Ａｃｕｓｔａ　ｄｅｓｐｅｃｔａ　ｓｉｅｂｏｌｄｉａｎａ）、ミスジマイマイ（Ｅｕｈａｄｒａ　ｐｅｌｉｏｍｐｈａｌａ）等の腹足類、
ミナミネグサレセンチュウ（Ｐｒａｔｈｙｌｅｎｃｈｕｓ　ｃｏｆｆｅａｅ）、キタネグサレセンチュウ（Ｐｒａｔｈｙｌｅｎｃｈｕｓ　ｐｅｎｅｔｒａｎｓ）、クルミネグサレセンチュウ（Ｐｒａｔｈｙｌｅｎｃｈｕｓ　ｖｕｌｎｕｓ）、ジャガイモシストセンチュウ（Ｇｌｏｂｏｄｅｒａ　ｒｏｓｔｏｃｈｉｅｎｓｉｓ）、ダイズシストセンチュウ（Ｈｅｔｅｒｏｄｅｒａ　ｇｌｙｃｉｎｅｓ）、キタネコブセンチュウ（Ｍｅｌｏｉｄｏｇｙｎｅ　ｈａｐｌａ）、サツマイモネコブセンチュウ（Ｍｅｌｏｉｄｏｇｙｎｅ　ｉｎｃｏｇｎｉｔａ）、イネシンガレセンチュウ（Ａｐｈｅｌｅｎｃｈｏｉｄｅｓ　ｂｅｓｓｅｙｉ）、マツノザイセンチュウ（Ｂｕｒｓａｐｈｅｌｅｎｃｈｕｓ　ｘｙｌｏｐｈｉｌｕｓ）等の線虫類、
等が挙げられるが、本発明はこれらのみに限定されるものではない。 Dust mites such as cyclamen dust mites (Phytonemus pallidus), chano mite mites (Polyphagotarsononemus latus), and mites (Tarsonmus bilobatus),
Spider mites (Penthaleus erythrocephalus), wheat mites (Penthaleus major), etc.,
Rice spider mites (Oligonychus shinkajii), citrus red spider mite (Pananychus citri), red spider mite (Pananychus ulmi), tick mite (Tananychus urticae), Tetranichus kanzawai
Tea Roh Naga rust mite (Acaphylla theavagrans), Tulip rust mite (Aceria tulipae), tomato rust mite (Aculops lycopersici), mandarin orange rust mite (Aculops pelekassi), apple rust mite (Aculus schlechtendali), false pear rust mite (Eriophyes chibaensis), citrus last mite (Phyllocoptruta oleivora )
Coniferous mites such as Robin tick (Rhizoglyphus robini), Pterocarpus mite (Tyrophagus putrescentiae), Spinach mite (Tyrophagus similis),
Bee mites such as honeybee mite (Varroa jacobsoni),
Boophilus microplus (Boophilus microplus), Rhipicephalus sanguineus (Rhipicephalus sanguineus), Haemaphysalis longicornis (Haemaphysalis longicornis), Haemaphysalis flava (Haemophysalis flava), Adenophora Chima mite (Haemophysalis campanulata), Yamatochimadani (Haemaphysalis japonica), Ootogechimadani (Haemaphysalis megaspinosa), Ixodes ovatus (Ixodes ovatus), schulze ticks (Ixodes persulcatus), foxtail ticks (Ixodes nipponensis), western black tick (Ixodes pacifcus), sheep Dick (Ixodes ricinus), Ixes scapularis, Lone star tick (Amblyomamma americanum), Amblyomamma aculatum, Dick tick (Amblyomamma ect) Ticks such as Rocky Mountain forest ticks (Dermentertor andrsononi), West Coast ticks (Demercentor occidentalis), American dog ticks (Dermentertor variabilis), tick ticks (Dermentertor spp.),
Crawfish ticks (Cheeletiella yasguri), crayfish ticks (Cheeletiella blackei), etc.,
Acne mites such as Inodemite mites (Demodex canis), Caterpillar mites (Demodex cati),
Cucumber mites such as ovine cucumber mites (Psoroptes ovis),
Mite mites such as Sarcoptes scabiei, catfish mite mite (Nototoresres cati), chicken mite mite (Knemidopoptes spp.),
Crustaceans such as Armadillium vulgare,
Pomacea caliculata, Achatina falica, slugs (Meghiatumium bilineatum), Chaikoura slugs (Limax Valentiana), Uskawamai (Acusta despae)
South Negu Saleh nematode (Prathylenchus coffeae), Northern Negu Saleh nematode (Prathylenchus penetrans), walnut Negu Saleh nematode (Prathylenchus vulnus), potato cyst nematode (Globodera rostochiensis), soybean cyst nematode (Heterodera glycines), northern root-knot nematode (Meloidogyne hapla), sweet potato Nematodes such as Meloidogyne incognita, Rice scentless nematode (Aphelenchodes besseyi), and pinewood nematode (Bursaphelenchus xylophilus),
However, the present invention is not limited to these examples.
　本発明化合物は、水田作物、畑作物、果樹、野菜、その他の作物及び花卉等の有用作物に被害を与える有害生物に対して顕著な防除効果を有するものであるので、有害生物の発生が予測される時期に合わせて、有害生物の発生前又は発生が確認された時点で、水田、畑、果樹、野菜、その他の作物、花卉等の水田水、茎葉又は土壌に処理することにより本発明の有害生物防除剤としての効果が得られるものである。 Since the compound of the present invention has a remarkable controlling effect on pests that damage useful crops such as paddy field crops, field crops, fruit trees, vegetables, other crops, and flowers, the occurrence of pests is predicted. The paddy field, fields, fruit trees, vegetables, other crops, flower paddies and other paddy water, stalks and leaves, or the soil of the present invention are processed before or after the occurrence of pests. The effect as a pest control agent is acquired.
　以下に、有害生物から有用作物を保護するために、本発明化合物の有効量を含む薬剤を、対象とする有用作物又は土壌に処理することを含む、薬剤の使用方法について述べる。 Hereinafter, in order to protect useful crops from pests, a method for using the drug including treating the useful crop or soil with a drug containing an effective amount of the compound of the present invention will be described.
　本発明化合物は、収穫物の保存中に発生する貯穀害虫等に対して顕著な防除効果を有するものである。すなわち、本発明化合物を有効成分とする有害生物防除剤を収穫物、あるいは収穫物の保存場所に、吹き付け、塗沫、塗布、浸漬、粉衣、薫蒸・薫煙又は加圧注入等の収穫後（ｐｏｓｔ　ｈａｒｖｅｓｔ）処理を行えばよい。 The compound of the present invention has a remarkable control effect against stored pests and the like generated during storage of harvested products. That is, a pest control agent comprising the compound of the present invention as an active ingredient is harvested by spraying, smearing, coating, dipping, dressing, fumigation / fumigation, pressurized injection, etc. What is necessary is just to perform a post (post harvest) process.
　本発明化合物は、植物種子に適用することにより、播種後の植物に発生する農業害虫等の有害生物による被害を予防することが出来る。すなわち、本発明化合物を有効成分とする有害生物防除剤をそのまま、又は水等で適宜希釈し、若しくは懸濁させた形で害虫防除に有効な量を、植物種子に対し吹き付け、塗沫、浸漬又は粉衣などの処理をすることにより、本発明化合物を植物種子に接触させればよい。
　この場合、植物種子とは、幼植物が発芽するための栄養分を蓄え農業上繁殖に用いられるものをいう。例えば、トウモロコシ、大豆、小豆、綿、稲、サトウダイコン、小麦、大麦、ヒマワリ、トマト、キュウリ、ナス、ホウレンソウ、サヤエンドウ、カボチャ、サトウキビ、タバコ、ピーマンおよびセイヨウアブラナなどの種子やサトイモ、バレイショ、カンショ、コンニャクなどの種芋、食用ゆり、チューリップなどの球根やラッキョウなどの種球などが挙げられる。 By applying the compound of the present invention to plant seeds, damage by pests such as agricultural pests generated on the plant after sowing can be prevented. That is, a pest control agent containing the compound of the present invention as an active ingredient is sprayed, smeared, or dipped on a plant seed in an amount effective for pest control as it is, or appropriately diluted with water or suspended. Alternatively, the compound of the present invention may be brought into contact with the plant seeds by treatment such as dressing.
In this case, the plant seeds refer to those that store nutrients for germination of young plants and are used for agricultural reproduction. For example, seeds such as corn, soybeans, red beans, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, sweet pea, pumpkin, sugar cane, tobacco, sweet pepper, rape, sweet potato , Seed seeds such as konjac, edible lily, bulbs such as tulips and seed balls such as raccoon.
　本発明化合物は、シロアリ、ヒラタキクイムシ、ナガシンクイムシ、シバンムシ、カミキリムシ等の木材食害虫に対して顕著な防除効果を有するものであり、土壌あるいは建築物等の木材に処理することにより、前記木材食害虫を防除することができる。
　本発明化合物は種々の有害生物に対して防除効果を示し、有用作物を保護する効果と共に、低薬量で殺虫剤又は殺ダニ剤として優れた防除効果を示すため、環境への負荷低減に大きく貢献する効果がある。 The compound of the present invention has a remarkable control effect against wood pests such as termites, oyster beetles, moth beetles, beetles, longhorn beetles, etc. Can control pests.
The compound of the present invention exhibits a control effect against various pests, and has an excellent control effect as an insecticide or acaricide at a low dose, in addition to the effect of protecting useful crops, greatly reducing the burden on the environment. There is an effect to contribute.
　本発明化合物を使用するにあたっては、通常適当な固体担体又は液体担体である不活性担体と混合し、更に所望により、補助剤として、界面活性剤、浸透剤、展着剤、増粘剤、凍結防止剤、結合剤、固結防止剤、崩壊剤、消泡剤、防腐剤および分解防止剤等を添加して、液剤（ｓｏｌｕｂｌｅ　ｃｏｎｃｅｎｔｒａｔｅ）、乳剤（ｅｍｕｌｓｉｆｉａｂｌｅ　ｃｏｎｃｅｎｔｒａｔｅ）、水和剤（ｗｅｔｔａｂｌｅ　ｐｏｗｄｅｒ）、水溶剤（ｗａｔｅｒ　ｓｏｌｕｂｌｅ　ｐｏｗｄｅｒ）、顆粒水和剤（ｗａｔｅｒ　ｄｉｓｐｅｒｓｉｂｌｅ　ｇｒａｎｕｌｅ）、顆粒水溶剤（ｗａｔｅｒ　ｓｏｌｕｂｌｅ　ｇｒａｎｕｌｅ）、懸濁剤（ｓｕｓｐｅｎｓｉｏｎ　ｃｏｎｃｅｎｔｒａｔｅ）、乳濁剤（ｃｏｎｃｅｎｔｒａｔｅｄ　ｅｍｕｌｓｉｏｎ）、サスポエマルジョン（ｓｕｓｐｏｅｍｕｌｓｉｏｎ）、マイクロエマルジョン（ｍｉｃｒｏｅｍｕｌｓｉｏｎ）、粉剤（ｄｕｓｔａｂｌｅ　ｐｏｗｄｅｒ）、粒剤（ｇｒａｎｕｌｅ）錠剤（ｔａｂｌｅｔ）、又は乳化性ゲル剤（ｅｍｕｌｓｉｆｉａｂｌｅ　ｇｅｌ）等を加えた組成物とすることで、任意の剤型の製剤にて実用に供することができる。また、省力化および安全性向上の観点から、上記任意の剤型の製剤を、水溶性カプセルおよび水溶性フィルムの袋等の水溶性包装体に封入して供することもできる。 When using the compound of the present invention, it is usually mixed with an inert carrier which is a suitable solid carrier or liquid carrier, and if desired, a surfactant, penetrant, spreading agent, thickener, freezing agent as an auxiliary agent. An inhibitor, a binder, an anti-caking agent, a disintegrant, an antifoaming agent, an antiseptic and an anti-decomposition agent, etc. are added, and a liquid agent, an emulsion, a wettable powder, Water solvent, water dispersible granule, water soluble granule, suspension concentrate, emulsion (concentrated emulsifier), water soluble powder, water dispersible granule, water soluble granule, water suspension concentrate. ion), suspoemulsion, microemulsion, dust powder, granule tablet, or emulsifiable gel. Thus, it can be put to practical use in preparations of any dosage form. Further, from the viewpoint of labor saving and safety improvement, the preparations of any of the above dosage forms can be provided by being enclosed in a water-soluble package such as a water-soluble capsule and a bag of a water-soluble film.
　また、本発明化合物を使用するにあたっては、本発明化合物と、不活性担体又は上記補助剤と、を混合した組成物にすることが好ましい。 In using the compound of the present invention, it is preferable to make a composition in which the compound of the present invention and an inert carrier or the above-mentioned auxiliary agent are mixed.
　本発明で使用できる不活性担体としては固体又は液体のいずれであってもよい。
　固体の不活性担体になりうる材料としては、例えば、ダイズ粉、穀物粉、木粉、樹皮粉、鋸粉、タバコ茎粉、クルミ殻粉、ふすま、繊維素粉末、植物エキス抽出後の残渣、粉砕合成樹脂などの合成重合体、粘土類（例えばカオリン、ベントナイト、酸性白土など）、タルク類（例えばタルク、ピロフィライドなど）、シリカ類（例えば珪藻土、珪砂、雲母、ホワイトカーボン〔含水微粉珪素、含水珪酸ともいわれる合成高分散珪酸で、製品により珪酸カルシウムを主成分として含むものもある。〕）、活性炭、イオウ粉末、軽石、焼成珪藻土、レンガ粉砕物、フライアッシュ、砂、炭酸カルシウム、リン酸カルシウムなどの無機鉱物性粉末、硫安、燐安、硝安、尿素、塩安などの化学肥料、堆肥などを挙げることができる。これらは単独でもしくは二種以上の混合物の形で使用される。 The inert carrier that can be used in the present invention may be either solid or liquid.
Examples of materials that can be used as a solid inert carrier include soybean powder, cereal powder, wood powder, bark powder, saw powder, tobacco stem powder, walnut shell powder, bran, fiber powder, residue after extraction of plant extracts, Synthetic polymers such as pulverized synthetic resins, clays (eg kaolin, bentonite, acid clay), talc (eg talc, pyrophyllide, etc.), silicas (eg diatomaceous earth, silica sand, mica, white carbon (hydrous finely divided silicon, hydrous) Synthetic high-dispersion silicic acid called silicic acid, some of which contain calcium silicate as the main component.]), Activated carbon, sulfur powder, pumice, calcined diatomaceous earth, brick ground, fly ash, sand, calcium carbonate, calcium phosphate, etc. Examples thereof include inorganic mineral powders, chemical fertilizers such as ammonium sulfate, phosphorous acid, ammonium nitrate, urea, and ammonium chloride, and compost. These are used alone or in the form of a mixture of two or more.
　液体の不活性担体になりうる材料としては、それ自体溶媒能を有するものの他、溶媒能を有さずとも補助剤の助けにより有効成分化合物を分散させうることとなるものから選択され、例えば代表例として次に上げる担体を例示できるが、これらは単独でもしくは２種以上の混合物の形で使用される。液体の不活性担体になりうる材料としては、例えば水、アルコール類（例えば、メタノール、エタノール、イソプロパノール、ブタノール、エチレングリコールなど）、ケトン類（例えばアセトン、メチルエチルケトン、メチルイソブチルケトン、ジイソブチルケトン、シクロヘキサノンなど）、エーテル類（例えばジエチルエーテル、ジオキサン、セロソルブ、ジイソプロピルエーテル、テトラヒドロフランなど）、脂肪族炭化水素類（例えばケロシン、鉱油など）、芳香族炭化水素類（例えばベンゼン、トルエン、キシレン、ソルベントナフサ、アルキルナフタレンなど）、ハロゲン化炭化水素類（例えばジクロロメタン、クロロホルム、四塩化炭素、クロロベンゼンなど）、エステル類（例えば酢酸エチル、酢酸ブチル、プロピオン酸エチル、フタル酸ジイソブチル、フタル酸ジブチル、フタル酸ジオクチルなど）、アミド類（例えばジメチルホルムアミド、ジエチルホルムアミド、ジメチルアセトアミドなど）、ニトリル類（例えばアセトニトリルなど）を挙げることができる。
　これら固体および液体担体は、単独で用いても２種以上を併用してもよい。 The material that can be a liquid inert carrier is selected from those having solvent ability itself and those that can disperse an active ingredient compound with the aid of an auxiliary agent without having solvent ability. As examples, the following carriers can be exemplified, but these are used alone or in the form of a mixture of two or more. Examples of materials that can be used as a liquid inert carrier include water, alcohols (eg, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.) ), Ethers (eg, diethyl ether, dioxane, cellosolve, diisopropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (eg, kerosene, mineral oil, etc.), aromatic hydrocarbons (eg, benzene, toluene, xylene, solvent naphtha, alkyl) Naphthalene etc.), halogenated hydrocarbons (eg dichloromethane, chloroform, carbon tetrachloride, chlorobenzene etc.), esters (eg ethyl acetate, butyl acetate, propionic acid) Chill, diisobutyl phthalate, dibutyl phthalate, phthalic acid dioctyl), amides (e.g. dimethylformamide, diethylformamide, dimethylacetamide, etc.), can be exemplified nitriles (e.g. acetonitrile, etc.).
These solid and liquid carriers may be used alone or in combination of two or more.
　界面活性剤としては、具体的には、例えばポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキル（モノ又はジ）フェニルエーテル、ポリオキシエチレン（モノ、ジ又はトリ）スチリルフェニルエーテル、ポリオキシエチレンポリオキシプロピレンブロックコポリマー、ポリオキシエチレン脂肪酸（モノ又はジ）エステル、ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ヒマシ油エチレンオキサイド付加物、アセチレングリコール、アセチレンアルコール、アセチレングリコールのエチレンオキサイド付加物、アセチレンアルコールのエチレンオキサイド付加物およびアルキルグリコシド等のノニオン性界面活性剤、アルキル硫酸エステル塩、アルキルベンゼンスルホン酸塩、リグニンスルホン酸塩、アルキルスルホコハク酸塩、ナフタレンスルホン酸塩、アルキルナフタレンスルホン酸塩、ナフタレンスルホン酸のホルマリン縮合物の塩、アルキルナフタレンスルホン酸のホルマリン縮合物の塩、ポリオキシエチレンアルキルエーテル硫酸又は燐酸エステル塩、ポリオキシエチレン（モノ又はジ）アルキルフェニルエーテル硫酸又は燐酸エステル塩、ポリオキシエチレン（モノ、ジ又はトリ）スチリルフェニルエーテル硫酸又は燐酸エステル塩、ポリカルボン酸塩（例えば、ポリアクリル酸塩、ポリマレイン酸塩およびマレイン酸とオレフィンとの共重合物等）およびポリスチレンスルホン酸塩等のアニオン性界面活性剤、アルキルアミン塩およびアルキル４級アンモニウム塩等のカチオン性界面活性剤、アミノ酸型およびベタイン型等の両性界面活性剤、シリコーン系界面活性剤ならびにフッ素系界面活性剤が挙げられる。
　これら界面活性剤の含有量は、特に限定されるものではないが、本発明の製剤１００重量部に対し、通常０．０５～２０重量部の範囲が望ましい。また、これら界面活性剤は、単独で用いても２種以上を併用してもよい。 Specific examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono or di) phenyl ether, polyoxyethylene (mono, di or tri) styryl phenyl ether, polyoxyethylene polyoxypropylene Block copolymer, polyoxyethylene fatty acid (mono or di) ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, castor oil ethylene oxide adduct, acetylene glycol, acetylene alcohol, ethylene oxide adduct of acetylene glycol, ethylene of acetylene alcohol Nonionic surfactants such as oxide adducts and alkyl glycosides, alkyl sulfate esters, alkylbenzene sulfonates, lignin sulfonic acids , Alkylsulfosuccinate, naphthalenesulfonate, alkylnaphthalenesulfonate, salt of formalin condensate of naphthalenesulfonic acid, salt of formalin condensate of alkylnaphthalenesulfonic acid, polyoxyethylene alkyl ether sulfate or phosphate ester, Oxyethylene (mono or di) alkyl phenyl ether sulfate or phosphate ester salt, polyoxyethylene (mono, di or tri) styryl phenyl ether sulfate or phosphate ester salt, polycarboxylate (eg, polyacrylate, polymaleate) And copolymers of maleic acid and olefins) and anionic surfactants such as polystyrene sulfonates, cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts, amino acid types and betaine types Amphoteric surfactants, and silicone-based surfactants and fluorinated surfactants.
The content of these surfactants is not particularly limited, but is preferably in the range of 0.05 to 20 parts by weight with respect to 100 parts by weight of the preparation of the present invention. These surfactants may be used alone or in combination of two or more.
　各種害虫を防除するためにそのまま、又は水などで適宜希釈し、もしくは懸濁させた形で病害防除に有効な量を当該害虫の発生が予測される作物もしくは発生が好ましくない場所に適用して使用すればよい。その使用量は種々の因子、例えば目的、対象害虫、作物の生育状況、害虫の発生傾向、天候、環境条件、剤型、施用方法、施用場所、施用時期などにより変動するが、一般に有効成分０．０００１～５０００ｐｐｍ、好ましくは０．０１～１０００ｐｐｍの濃度で使用するのが好ましい。また、１０ａあたりの施用量は、一般に有効成分で１～３００ｇである。 Applying an effective amount for disease control in the form of a pest control or a place where the occurrence of the pest is unfavorable as it is, or appropriately diluted or suspended in water to control various pests Use it. The amount used varies depending 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. It is preferably used at a concentration of 0.0001 to 5000 ppm, preferably 0.01 to 1000 ppm. The application amount per 10a is generally 1 to 300 g as an active ingredient.
本発明の一般式（Ｉ）で表される化合物の有効成分量は、０．１～９０重量％、好ましくは３～９０重量％、より好ましくは５～９０重量％、更により好ましくは５～５０重量％、最も好ましくは５～２０重量％である。 The amount of the active ingredient of the compound represented by the general formula (I) of the present invention is 0.1 to 90% by weight, preferably 3 to 90% by weight, more preferably 5 to 90% by weight, still more preferably 5 to 50% by weight, most preferably 5-20% by weight.
　本発明の一般式（Ｉ）で表される化合物の有効成分量は、通常粉剤では０．１～２０重量％、乳剤では５～５０重量％、水和剤では３～９０重量％、粒剤では０．１～２０重量％およびフロアブル製剤では５～９０重量％、顆粒水和剤では３～９０重量％である。一方それぞれの剤型における担体の量は、通常粉剤では６０～９９．９重量％、乳剤では４０～９５重量％、水和剤では１０～９０重量％、粒剤では８０～９９．９重量％、およびフロアブル製剤では１０～９５重量％、顆粒水和剤では１０～９０重量％である。また、補助剤の量は、通常粉剤では０．１～２０重量％、乳剤では１～２０重量％、水和剤では０．１～２０重量％、粒剤では０．１～２０重量％およびフロアブル製剤では０．１～２０重量％、顆粒水和剤では０．１～２０重量％である。
　また、本発明化合物を農薬として使用する場合には、必要に応じて製剤時又は散布時に他種の除草剤、各種殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、植物生長調節剤、共力剤、肥料、土壌改良剤等と混合施用してもよい。 The amount of the active ingredient of the compound represented by formula (I) of the present invention is usually 0.1 to 20% by weight for powders, 5 to 50% by weight for emulsions, 3 to 90% by weight for wettable powders, and granules. Is 0.1 to 20% by weight, 5 to 90% by weight for flowable preparations, and 3 to 90% by weight for granular wettable powders. On the other hand, the amount of carrier in each dosage form is usually 60 to 99.9% by weight for powders, 40 to 95% by weight for emulsions, 10 to 90% by weight for wettable powders, and 80 to 99.9% by weight for granules. And 10 to 95% by weight for flowable preparations and 10 to 90% by weight for granular wettable powders. The amount of the adjuvant is usually 0.1 to 20% by weight for powders, 1 to 20% by weight for emulsions, 0.1 to 20% by weight for wettable powders, 0.1 to 20% by weight for granules, and The flowable preparation is 0.1 to 20% by weight, and the granule wettable powder is 0.1 to 20% by weight.
In addition, when using the compound of the present invention as an agrochemical, other types of herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, as necessary, at the time of formulation or spraying, You may mix and apply with a synergist, a fertilizer, a soil improvement agent, etc.
　本発明化合物は、双翅目害虫（アカイエカ、チカイエカ、ユスリカ、イエバエ、チョウバエ、ウシアブ等）、網翅目害虫（チャバネゴキブリ、クロゴキブリ、ワモンゴキブリ等）等の衛生害虫に対して顕著な防除効果を有するものである。
さらに本発明化合物は、直接の危害を与える節足動物類あるいは病気の媒介者である節足動物類等の駆虫剤として、それらの害生物が潜在しうる周囲の環境に対して、油剤や、乳剤、水和剤等の散布・注入・灌注・塗布、粉剤等の散布、薫蒸剤、蚊取線香・自己燃焼型燻煙剤、化学反応型煙霧剤等の加熱煙霧剤、フォッギング等の燻煙剤、ULV剤等の処理、顆粒、錠剤及び毒餌の設置、又はフローティング粉剤、粒剤等の水路、井戸、貯水池、貯水槽及びその他の流水もしくは停留水中への滴下等の方法で利用することもできる。更に、農業、森林害虫でもあるドクガ類等に対しては、前記した方法と同様に防除することが可能であり、又はハエ類等に対しては家畜の飼料中に混入して糞に混じるようにする方法、カ類等に対しては電気蚊取器等で空中へ揮散させる方法等も有効である。なお、これらの使用形態である製剤は、他の活性化合物、例えば殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、忌避剤又は共力剤との混合剤として存在することもでき、これらの製剤は、本発明化合物を合計量で、例えば、０．０００１～９５質量％含有することが適当である。 The compound of the present invention has a remarkable control effect against sanitary pests such as Diptera pests (Acaeca, Chicaeka, Chironae, houseflies, butterflies, cattle fly, etc.), reticulate pests (Chebrobella, black cockroach, American cockroach, etc.) Is.
Furthermore, the compound of the present invention is used as an anthelmintic agent for arthropods that cause direct harm, or for arthropods that are disease vectors, against oils, Emulsions, wettable powders, injection, irrigation, application, dusting, fumigants, mosquito coils, self-burning smokes, chemical reaction fumes, etc. Use by methods such as treatment with smoke, ULV, etc., installation of granules, tablets and poisonous bait, or dripping into floating waterways, wells, reservoirs, water tanks, and other running water or water. You can also. In addition, it is possible to control the stag beetles, which are also agricultural and forest pests, in the same manner as described above, or for the flies and the like so that they are mixed in the feed of livestock. For example, a method of volatilizing it into the air with an electric mosquito trap etc. is also effective. The preparations in these use forms can exist as a mixture with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists. It is appropriate that the preparation of the present invention contains the compound of the present invention in a total amount, for example, 0.0001 to 95% by mass.
　本発明化合物は、ネコノミ、イヌノミ、フタトゲチマダニ、糸状虫科(Filariidae)線虫類等の、家畜及び愛玩動物等の人間以外の哺乳動物及び鳥類の外部又は内部寄生虫を防除することができる。
　外部・内部寄生虫の防除は、経口投与、非経口的投与又は経皮投与により達成される。
　経口投与としては、本発明化合物を少量、食事又は飼料等に混入したり、適切な経口摂取可能な調合薬剤組成物等の経口投与剤、例えば、薬剤上許容しうる担体や、コーティング物質を含む錠剤、丸剤（丸薬）、カプセル剤、除放性大粒丸薬、ペースト剤、ゲル剤、薬用飲料、薬用飼料、薬用飲料水、動物飼料、薬用追餌、その他胃腸管内に保留されるようにした除放性デバイス等の経口投与剤として調製し、これらを家畜、ペットに傾向的に投与すればよい。
　薬用飲料水として経口的に投与する場合、飲料は普通ベントナイトのような懸濁剤あるいは湿潤剤又はその他の賦形剤と共に適当な非毒性の溶剤又は水での溶解、懸濁液又は分散液である。また、一般に薬用飲料水はまた消泡剤を含有する。薬用飲料水処方は、一般に本発明化合物を０．０１～１．０質量％、好ましくは、０．０１～０．１質量％を含有することができる。 The compound of the present invention can control external or endoparasites of mammals and birds other than humans such as domestic animals and pets, such as cat fleas, dog fleas, spider mites, and Filariidae nematodes.
Control of ectoparasites and endoparasites can be achieved by oral administration, parenteral administration or transdermal administration.
Oral administration includes a small amount of the compound of the present invention in a meal, feed, or the like, or an oral administration agent such as a pharmaceutical composition that can be taken orally, such as a pharmaceutically acceptable carrier and a coating substance. Tablets, pills (pills), capsules, sustained-release large pills, pastes, gels, medicinal drinks, medicinal feeds, medicinal drinking water, animal feeds, medicinal supplements, and other gastrointestinal tracts What is necessary is just to prepare as oral administration agents, such as a sustained-release device, and to administer these to livestock and a pet tendency.
When administered orally as a medicinal drinking water, the beverage is usually dissolved, suspended or dispersed in a suitable non-toxic solvent or water with a suspending or wetting agent such as bentonite or other excipients. is there. In general, medicinal drinking water also contains an antifoaming agent. The medicinal drinking water formulation can generally contain 0.01 to 1.0% by mass, preferably 0.01 to 0.1% by mass of the compound of the present invention.
　乾燥した個体の単位使用形態で経口的に投与することが望ましい場合は、通常所定量の有効成分を含有するカプセル、丸薬又は錠剤を用いる。これらの使用形態は、活性成分を適当に細粉砕した希釈剤、充填剤、崩壊剤及び／又は結合剤、例えばデンプン、乳糖、タルク、ステアリン酸マグネシウム、植物性ゴム等と均質に混和することによって製造される。このような乾燥した固体の単位使用処方は、治療される宿主動物の種類、感染の程度及び寄生虫の種類及び宿主の体重によって駆虫剤の質量及び含量を広く変化させることができる。
　動物飼料によって投与する場合は、それを飼料に均質に分散させるか、トップドレッシングとして使用されるかペレットの形態として使用できる。普通望ましい抗寄生虫効果を達成するためには、最終飼料中に本発明化合物を、例えば、０．０００１～０．０５質量％、好ましくは、０．０００５～０．０１質量％を含有させることもできる。 When it is desired to administer orally in a dry individual unit dosage form, capsules, pills or tablets containing a predetermined amount of the active ingredient are usually used. These forms of use are obtained by intimately mixing the active ingredient with suitably finely divided diluents, fillers, disintegrants and / or binders such as starch, lactose, talc, magnesium stearate, vegetable gums and the like. Manufactured. Such dry solid unit use formulations can vary widely in the anthelmintic mass and content depending on the type of host animal being treated, the degree of infection and the type of parasite and the body weight of the host.
When administered by animal feed, it can be dispersed homogeneously in the feed, used as a top dressing or in the form of pellets. In order to achieve a generally desirable antiparasitic effect, the compound of the present invention contains, for example, 0.0001 to 0.05% by mass, preferably 0.0005 to 0.01% by mass, in the final feed. You can also.
　経皮投与としては、スプレー、粉末、グリース、クリーム、軟膏、乳剤、ローション、スポットオン、ポアオン、シャンプー等の経皮投与剤として経皮投与又は局所投与すればよい。
　経皮投与や局所投与の方法として、局部的又は全身的に節足動物を防除するように動物に取り付けたデバイス（例えば首輪、メダリオンやイヤータッグ等）を利用することもできる。
　この様な経皮投与や局所投与の効果を達成するためには、一般に本発明化合物で０．０００１～０．１質量％、好ましくは、０．００１～０．０１質量％を投与させればよい。 For transdermal administration, it may be administered as a transdermal agent such as spray, powder, grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo, or the like.
As a method of transdermal administration or local administration, a device (for example, a collar, a medallion, an ear tag, etc.) attached to an animal so as to control an arthropod locally or systemically can be used.
In order to achieve such effects of transdermal administration or topical administration, generally 0.0001 to 0.1% by mass, preferably 0.001 to 0.01% by mass of the compound of the present invention is administered. Good.
　液体担体賦形剤に溶解あるいは分散させたものは、前胃内、筋肉内、気管内又は皮下注射によって非経口的に動物に投与できる。非経口投与のために、活性化合物は好適には落花生油、綿実油のような適当な植物油と混合する。このような処方は、一般に本発明化合物を０．０５～５０質量％、好ましくは、０．１～５．０質量％を含有させることができる。
　また、ジメチルスルホキシドや、炭化水素溶剤のような適当な担体と混合することによって局所的に投与しうる。この製剤はスプレー又は直接的注加によって動物の外部表面に直接適用される。 Those dissolved or dispersed in a liquid carrier vehicle can be administered parenterally to animals by intragastric, intramuscular, intratracheal or subcutaneous injection. For parenteral administration, the active compounds are preferably mixed with suitable vegetable oils, such as peanut oil, cottonseed oil. Such a formulation can generally contain 0.05 to 50% by mass, preferably 0.1 to 5.0% by mass of the compound of the present invention.
It can also be administered topically by mixing with a suitable carrier such as dimethyl sulfoxide or a hydrocarbon solvent. This formulation is applied directly to the external surface of the animal by spraying or direct injection.
　本発明化合物は、本発明化合物と、本発明化合物とは異なる、他の殺虫剤及び／又は殺菌剤のうち１種以上と、を組み合わせた混合物として用いることによっても優れた防除効果を奏するものである。
　他の殺虫剤及び／又は殺菌剤としては、例えば、他の農園芸用殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、除草剤、植物成長調節剤、又は生物農薬等が挙げられる。 The compound of the present invention exhibits an excellent control effect even when used as a mixture of the compound of the present invention and one or more of other insecticides and / or fungicides different from the compound of the present invention. is there.
Examples of other insecticides and / or fungicides include other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, biological pesticides, and the like.
　本発明の有害生物防除混合剤において、本発明化合物と組み合わせることができる化合物としては、例えば殺虫剤、殺ダニ剤、殺線虫剤としてはピレスロイド系化合物、有機リン系化合物、オキシム・カーバメート系化合物、カーバメート系化合物、ネオニコチノイド系化合物、ジアシルヒドラジン系化合物、ベンゾイルウレア系化合物、幼若ホルモン系化合物、シクロジエン有機塩素系化合物、２－ジメチルアミノプロパン－１，３－ジチオール系化合物、アミジン系化合物、フェニルピラゾール系化合物、有機スズ系化合物、ＭＥＴＩ系化合物、ベンジレート系化合物、アリルピロール系化合物、ジニトロフェノール系化合物、アントラニル・ジアミド系化合物、オキサジアジン系化合物、セミカルバゾン系化合物、テトロン酸系化合物、カルバモイルトリアゾール系化合物、テトラジン系化合物などから選ばれる化合物を挙げることができ、殺菌剤としてはストロビルリン系化合物、アニリノピリミジン系化合物、アゾール系化合物、アゾール系化合物、ジチオカーバメート系化合物、フェニルカーバメート系化合物、有機塩素系化合物、ベンズイミダゾール系化合物、フェニルアミド系化合物、スルフェン酸系化合物、銅系化合物、イソキサゾール系化合物、有機リン系化合物、Ｎ－ハロゲノチオアルキル系化合物、カルボキシアニリド系化合物、モルフォリン系化合物、有機スズ系化合物、シアノピロール系化合物などから選ばれる化合物を挙げることができ、クロルピクリン（ｃｈｌｏｒｏｐｉｃｒｉｎ）等のくん蒸剤、ニコチン（ｎｉｃｏｔｉｎｅ）等の天然物化合物を挙げることもできる。また上記の群以外の化合物も挙げることができる。 Examples of the compound that can be combined with the compound of the present invention in the pest control mixture of the present invention include insecticides, acaricides, pyrethroid compounds, organophosphorus compounds, oxime carbamate compounds as nematicides , Carbamate compounds, neonicotinoid compounds, diacylhydrazine compounds, benzoyl urea compounds, juvenile hormone compounds, cyclodiene organochlorine compounds, 2-dimethylaminopropane-1,3-dithiol compounds, amidine compounds , Phenylpyrazole compounds, organotin compounds, METI compounds, benzylate compounds, allylpyrrole compounds, dinitrophenol compounds, anthranyl diamide compounds, oxadiazine compounds, semicarbazone compounds, tetronic acid compounds , Carbamoyltriazole compounds, tetrazine compounds, and the like. Examples of bactericides include strobilurin compounds, anilinopyrimidine compounds, azole compounds, azole compounds, dithiocarbamate compounds, phenyl carbamate compounds. Compounds, organochlorine compounds, benzimidazole compounds, phenylamide compounds, sulfenic acid compounds, copper compounds, isoxazole compounds, organophosphorus compounds, N-halogenothioalkyl compounds, carboxyanilide compounds, morpholines Compounds selected from organic compounds, organotin compounds, cyanopyrrole compounds, and the like, fumigants such as chloropicrin, and natural products such as nicotine Mention may also be made of things. Further, compounds other than the above groups can also be mentioned.
　具体的には例えば以下の化合物を挙げることができる。
　アクリナトリン（ａｃｒｉｎａｔｈｒｉｎ）、アレスリン（ａｌｌｅｔｈｒｉｎ）［（１Ｒ）－アイソマー］、ビフェントリン（ｂｉｆｅｎｔｈｒｉｎ）、ビオアレスリン（ｂｉｏａｌｌｅｔｈｒｉｎ）、ビオアレスリン　Ｓ－シクロペンテニル　アイソマー（ｂｉｏａｌｌｅｔｈｒｉｎ　Ｓ－ｃｙｃｌｏｐｅｎｔｅｎｙｌ　　ｉｓｏｍｅｒ）、ビオレスメトリン（ｂｉｏｒｅｓｍｅｔｈｒｉｎ）、シクロプロトリン（ｃｙｃｌｏｐｒｏｔｈｒｉｎ）、シフルトリン（ｃｙｆｌｕｔｈｒｉｎ）、ベータ－シフルトリン（ｂｅｔａ－ｃｙｆｌｕｔｈｒｉｎ）、シハロトリン（ｃｙｈａｌｏｔｈｒｉｎ）、ガンマ－シハロトリン（ｇａｍｍａ－ｃｙｈａｌｏｔｈｒｉｎ）、ラムダ－シハロトリン（ｌａｍｂｄａ－ｃｙｈａｌｏｔｈｒｉｎ）、シペルメトリン（ｃｙｐｅｒｍｅｔｈｒｉｎ）、アルファ－シペルメトリン（ａｌｐｈａ－ｃｙｐｅｒｍｅｔｈｒｉｎ）、ベータ－シペルメトリン（ｂｅｔａ－ｃｙｐｅｒｍｅｔｈｒｉｎ）、セタ－シペルメトリン（ｔｈｅｔａ－ｃｙｐｅｒｍｅｔｈｒｉｎ）、ゼダ－シペルメトリン（ｚｅｔａ－ｃｙｐｅｒｍｅｔｈｒｉｎ）、シフェノトリン［（１Ｒ）－トランス－アイソマー］（ｃｙｐｈｅｎｏｔｈｒｉｎ　［（１Ｒ）－ｔｒａｎｓ－ｉｓｏｍｅｒ］）、デルタメトリン（ｄｅｌｔａｍｅｔｈｒｉｎ）、エンペントリン［（ＥＺ）－（１Ｒ）－アイソマー］（ｅｍｐｅｎｔｈｒｉｎ［（ＥＺ）－（１Ｒ）－ｉｓｏｍｅｒ］）、エスフェンバレレート（ｅｓｆｅｎｖａｌｅｒａｔｅ）、エトフェンプロックス（ｅｔｈｏｆｅｎｐｒｏｘ）、フェンプロパトリン（ｆｅｎｐｒｏｐａｔｈｒｉｎ）、フェンバレレート（ｆｅｎｖａｌｅｒａｔｅ）、フルシトリネート（ｆｌｕｃｙｔｈｒｉｎａｔｅ）、フルメトリン（ｆｌｕｍｅｔｈｒｉｎ）、タウ－フルバリネート（ｔａｕ－ｆｌｕｖａｌｉｎａｔｅ）、ハルフェンプロックス（ｈａｌｆｅｎｐｒｏｘ）、イミプロトリン（ｉｍｉｐｒｏｔｈｒｉｎ）、メトトリン（ｍｅｔｈｏｔｈｒｉｎ）、メトフルトリン（ｍｅｔｏｆｌｕｔｈｒｉｎ）、ペルメトリン（ｐｅｒｍｅｔｈｒｉｎ）、フェノトリン［（１Ｒ）－トランス－アイソマー］（ｐｈｅｎｏｔｈｒｉｎ［（１Ｒ）－ｔｒａｎｓ－ｉｓｏｍｅｒ］）、プラレトリン（ｐｒａｌｌｅｔｈｒｉｎ）、レスメトリン（ｒｅｓｍｅｔｈｒｉｎ）、ＲＵ１５５２５（カデトリン（ｋａｄｅｔｈｒｉｎ））、シラフルオフェン（ｓｉｌａｆｌｕｏｆｅｎ）、テフルトリン（ｔｅｆｌｕｔｈｒｉｎ）、テトラメトリン（ｔｅｔｒａｍｅｔｈｒｉｎ）、テトラメトリン［（１Ｒ）－アイソマー］（ｔｅｔｒａｍｅｔｈｒｉｎ［（１Ｒ）－ｉｓｏｍｅｒ］）、トラロメトリン（ｔｒａｌｏｍｅｔｈｒｉｎ）、トランスフルトリン（ｔｒａｎｓｆｌｕｔｈｒｉｎ）、ＺＸＩ８９０１、バイオペルメトリン（ｂｉｏｐｅｒｍｅｔｈｒｉｎ）、フラメトリン（ｆｕｒａｍｅｔｈｒｉｎ）、プロフルトリン（ｐｒｏｆｌｕｔｈｒｉｎ）、フルブロシトリネート（ｆｌｕｂｒｏｃｙｔｈｒｉｎａｔｅ）、ジメフルトリン（ｄｉｍｅｆｌｕｔｈｒｉｎ）等のピレスロイド系化合物およびこれらの各種異性体、 Specific examples include the following compounds.
Acrinathrin, allethrin [(1R) -isomer], bifenthrin, bioallethrin, bioarethrin S-cyclopentenyl isomer, S-cyclopentenyl isomer, S-cyclopentenyl isomer, S Cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin (lamb cythothrin) (Cypermethrin), alpha-cypermethrin (beta-cypermethrin), seta-cypermethrin (zeta-cypermethrin (zeta-cypermethrin)) ) -Trans-isomer] (cyphenothrin [(1R) -trans-isomer]), deltamethrin, empentrin [(EZ)-(1R) -isomer] (empentrin [(EZ)-(1R) -isomer)) , Esfenvalerate, etofenprox, fenpropa Phosphoproprin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, imiprothrin Metofluthrin, permethrin, phenothrin [(1R) -trans-isomer] (phenothrin [(1R) -trans-somer]), praretrin (resthrin), RU15 (resde), RU15 , Silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) -isomer], tralomethrin (in) 89, transfluthrin (in), ns Pyrethroid compounds such as permethrin, furamethrin, profluthrin, flubrocytrinate, dimefluthrin, and various isomers thereof,
　アセフェート（ａｃｅｐｈａｔｅ）、アザメチホス（ａｚａｍｅｔｈｉｐｈｏｓ）、アジンホス－メチル（ａｚｉｎｐｈｏｓ－ｍｅｔｈｙｌ）、アジンホス－エチル（ａｚｉｎｐｈｏｓ－ｅｔｈｙｌ）、カズサホス（ｃａｄｕｓａｆｏｓ）、クロルエトキシホス（ｃｈｌｏｒｅｔｈｏｘｙｆｏｓ）、クロルフェンビンホス（ｃｈｌｏｒｆｅｎｖｉｎｐｈｏｓ）、クロルメホス（ｃｈｌｏｒｍｅｐｈｏｓ）、クロルピリホス（ｃｈｌｏｒｐｙｒｉｆｏｓ）、クロルピリホス－メチル（ｃｈｌｏｒｐｙｒｉｆｏｓ－ｍｅｔｈｙｌ）、クマホス（ｃｏｕｍａｐｈｏｓ）、ＣＹＡＰ（シアノホス（ｃｙａｎｏｐｈｏｓ））、デメトン－Ｓ－メチル（ｄｅｍｅｔｏｎ－Ｓ－ｍｅｔｈｙｌ）、ダイアジノン（ｄｉａｚｉｎｏｎ）、ＥＣＰ（ジクロフェンチオン（ｄｉｃｈｌｏｆｅｎｔｈｉｏｎ））、ＤＤＶＰ（ジクロルボス（ｄｉｃｈｌｏｒｖｏｓ））、ジクロトホス（ｄｉｃｒｏｔｏｐｈｏｓ）、ジメトエート（ｄｉｍｅｔｈｏａｔｅ）、ジメチルビンホス（ｄｉｍｅｔｈｙｌｖｉｎｐｈｏｓ）、ジスルホトン（エチルチオメトン）（ｄｉｓｕｌｆｏｔｏｎ）、ＥＰＮ（Ｏ－エチル　Ｏ－４－ニトロフェニル　フェニルホスホノチオアート（Ｏ－ｅｔｈｙｌ　Ｏ－４－ｎｉｔｒｏｐｈｅｎｙｌ　ｐｈｅｎｙｌｐｈｏｓｐｈｏｎｏｔｈｉｏａｔｅ））、エチオン（ｅｔｈｉｏｎ）、エトプロホス（ｅｔｈｏｐｒｏｐｈｏｓ）、ファムフール（Ｆａｍｐｈｕｒ）、フェナミホス（ｆｅｎａｍｉｐｈｏｓ）、ＭＥＰ（フェニトロチオン（ｆｅｎｉｔｒｏｔｈｉｏｎ））、ＭＰＰ（フェンチオン（ｆｅｎｔｈｉｏｎ））、ホスチアゼート（ｆｏｓｔｈｉａｚａｔｅ）、ヘプテノホス（ｈｅｐｔｅｎｏｐｈｏｓ）、イソフェンホス－メチル（ｉｓｏｆｅｎｐｈｏｓ－ｍｅｔｈｙｌ）、イソカルボホス（Ｉｓｏｃａｒｂｏｐｈｏｓ）（イソプロピル　Ｏ－（メトキシアミノチオ＝ホスホリル）サリチラート）、イソキサチオン（ｉｓｏｘａｔｈｉｏｎ）、マラチオン（ｍａｌａｔｈｉｏｎ）、メカルバム（ｍｅｃａｒｂａｍ）、メタミドホス（ｍｅｔｈａｍｉｄｏｐｈｏｓ）、ＤＭＴＰ（メチダチオン（ｍｅｔｈｉｄａｔｈｉｏｎ））、メビンホス（ｍｅｖｉｎｐｈｏｓ）、モノクロトホス（ｍｏｎｏｃｒｏｔｏｐｈｏｓ）、ＢＲＰ（ナレッド（ｎａｌｅｄ））、オメトエート（ｏｍｅｔｈｏａｔｅ）、オキシデメトン－メチル（ｏｘｙｄｅｍｅｔｏｎ－ｍｅｔｈｙｌ）、パラチオン（ｐａｒａｔｈｉｏｎｓ）、パラチオン－メチル（ｐａｒａｔｈｉｏｎ－ｍｅｔｈｙｌ）、ＰＡＰ（フェントエート（ｐｈｅｎｔｈｏａｔｅ））、ホレート（ｐｈｏｒａｔｅ）、ホサロン（ｐｈｏｓａｌｏｎｅ）、ホスメット（ｐｈｏｓｍｅｔ）、ホスファミドン（ｐｈｏｓｐｈａｍｉｄｏｎ）、ホキシム（ｐｈｏｘｉｍ）、ピリミホス－メチル（ｐｉｒｉｍｉｐｈｏｓ－ｍｅｔｈｙｌ）、プロフェノホス（ｐｒｏｆｅｎｏｆｏｓ）、プロペタンホス（ｐｒｏｐｅｔａｍｐｈｏｓ）、プロチオホス（ｐｒｏｔｈｉｏｆｏｓ）、ピラクロホスピラクロホス（ｐｙｒａｃｌｏｆｏｓ）、ピリダフェンチオン（ｐｙｒｉｄａｐｈｅｎｔｈｉｏｎ）、キナルホス（ｑｕｉｎａｌｐｈｏｓ）、スルホテップ（Ｓｕｌｆｏｔｅｐ）、テブピリムホス（ｔｅｂｕｐｉｒｉｍｆｏｓ）、テメホス（ｔｅｍｅｐｈｏｓ）、テルブホス（ｔｅｒｂｕｆｏｓ）、チオメトン（ｔｈｉｏｍｅｔｏｎ）、トリアゾホス（ｔｒｉａｚｏｐｈｏｓ）、ＤＥＰ（トリクロルホン（ｔｒｉｃｈｌｏｒｆｏｎ））、バミドチオン（ｖａｍｉｄｏｔｈｉｏｎ）、Ｂａｙｅｒ　２２／１９０　（クロルチオン（ｃｈｌｏｒｏｔｈｉｏｎ））、ブロムフェンビンホス（ｂｒｏｍｆｅｎｖｉｎｆｏｓ）、ブロモホス（ｂｒｏｍｏｐｈｏｓ）、ブロモホス－エチル（ｂｒｏｍｏｐｈｏｓ－ｅｔｈｙｌ）、ブタチオホス（ｂｕｔａｔｈｉｏｆｏｓ）、カルボフェノチオン（ｃａｒｂｏｐｈｅｎｏｔｈｉｏｎ）、クロルホキシム（Ｃｈｌｏｒｐｈｏｘｉｍ）、スルプロホス（ｓｕｌｐｒｏｆｏｓ）、ジアミダホス（ｄｉａｍｉｄａｆｏｓ）、ＣＶＭＰ（テトラクロルビンホス（ｔｅｔｒａｃｈｌｏｒｖｉｎｐｈｏｓ））、プロパホス（ｐｒｏｐａｐｈｏｓ）、メスルフェンホス（ｍｅｓｕｌｆｅｎｆｏｓ）、ジオキサベンゾホス（サリチオン）（ｄｉｏｘａｂｅｎｚｏｆｏｓ）、エトリムホス（ｅｔｒｉｍｆｏｓ）、オキシデプロホス（ｏｘｙｄｅｐｒｏｆｏｓ）、ホルモチオン（ｆｏｒｍｏｔｈｉｏｎ）、フェンスルホチオン（ｆｅｎｓｕｌｆｏｔｈｉｏｎ）、イサゾホス（ｉｓａｚｏｆｏｓ）、イミシアホス（ｉｍｉｃｙａｆｏｓ）（ＡＫＤ３０８８）、イサミドホス（ｉｓａｍｉｄｏｆｏｓ）、チオナジン（ｔｈｉｏｎａｚｉｎ）、ホスチエタン（ｆｏｓｔｈｉｅｔａｎ）等の有機リン系化合物、 Acephate, azamethiphos, azinephos-methyl, azinephos-ethyl, cadusafos, chlorethoxyphos, chlorfenfos, chlorfenfos chlormephos, chloropyrifos, chlorpyrifos-methyl, coumaphos, CYAP (cyanophos), demeton-S-methyldi, EC, dinon-S-methydi, EC Diclofen ON (diclofenthion), DDVP (dichlorvos), dicrotophos, dimethoate, dimethylvinphos, disulfoton (ethylthiomethone), EPN (O-ethyl) Phenylphosphonothioate (O-ethyl O-4-nitrophenyl phenylphosphiothioate), Ethion, ethoprophos, Famfur, Fenamiphos, MEP (fenitrothion) nthion), fosthiazate, heptenophos, isofenphos-methyl, isocarbophos (isopropyl O- (methoxyaminothio = phosphoryl) salicylate), isoxathion (isthion) , Mecarbam, methamidophos, DMTP (methidathion), mevinphos, monocrotophos, BRP (naled), ometoate, oxide-methyl ton-methyl, parathion, parathion-methyl, PAP (phentoate), folate, fosalone, phosmetimidon, phosphamidone, phophamidon x ), Pirimiphos-methyl, profenofos, propetanephos, prothiophos, pyraclofphos, pyridafenthionphos, pyridafenthionphos otep, tebupyrimfos, temefos, terbufos, thiomethon, triazophos, DEP (trichlorfon), bidothion (v) ), Bromfenvinfos, bromophos, bromophos-ethyl, butathiofos, carbophenothion, chlorophoprom, sulfoprosim Amidafos (diamidafos), CVMP (tetrachlorvinphos), propaphos, mesulfenfos, dioxabenzophos (salithione), etrimfos (oxydemofos), etrimfosfo (Formation), fensulfothion, isazofos, imicyafos (AKD3088), isamidofos, thionazine, organic compounds such as thothiethane, etc.
　ホスホカルブ（ｐｈｏｓｐｈｏｃａｒｂ）、アラニカルブ（ａｌａｎｙｃａｒｂ）、ブトカルボキシム（ｂｕｔｏｃａｒｂｏｘｉｍ）、ブトキシカルボキシム（ｂｕｔｏｘｙｃａｒｂｏｘｉｍ）、チオジカルブ（ｔｈｉｏｄｉｃａｒｂ）、チオファノックス（Ｔｈｉｏｆａｎｏｘ）等のオキシム・カーバメート系化合物、 Oxime compounds such as phosphocarb, alaniccarb, butocarboxim, butoxycarboxim, thiodicarb, thiophanox, and thiophanox
　アルジカルブ（ａｌｄｉｃａｒｂ）、ベンジオカルブ（ｂｅｎｄｉｏｃａｒｂ）、ベンフラカルブ（ｂｅｎｆｕｒａｃａｒｂ）、ＮＡＣ（カルバリル（ｃａｒｂａｒｙｌ））、カルボフラン（ｃａｒｂｏｆｕｒａｎ）、カルボスルファン（ｃａｒｂｏｓｕｌｆａｎ）、エチオフェンカルブ（ｅｔｈｉｏｆｅｎｃａｒｂ）、ＢＰＭＣ（フェノブカルブ（ｆｅｎｏｂｕｃａｒｂ））、ホルメタネート（Ｆｏｒｍｅｔａｎａｔｅ）、フラチオカルブ（ｆｕｒａｔｈｉｏｃａｒｂ）、ＭＩＰＣ（イソプロカルブ（ｉｓｏｐｒｏｃａｒｂ））、メチオカルブ（ｍｅｔｈｉｏｃａｒｂ）、メソミル（ｍｅｔｈｏｍｙｌ）、オキサミル（ｏｘａｍｙｌ）、ピリミカーブ（ｐｉｒｉｍｉｃａｒｂ）、ＰＨＣ（プロポキスル（ｐｒｏｐｏｘｕｒ））、トリメタカルブ（ｔｒｉｍｅｔｈａｃａｒｂ）、ＸＭＣ（３，５－ｘｙｌｙｌ　ｍｅｔｈｙｌｃａｒｂａｍａｔｅ）、アリキシカルブ（ａｌｌｙｘｙｃａｒｂ）、アルドキシカルブ（ａｌｄｏｘｙｃａｒｂ）、ブフェンカルブ（ｂｕｆｅｎｃａｒｂ）、ブタカルブ（ｂｕｔａｃａｒｂ）、カーバノレート（ｃａｒｂａｎｏｌａｔｅ）、ＭＴＭＣ（メトルカルブ（ｍｅｔｏｌｃａｒｂ））、ＭＰＭＣ（キシルイルカルブ（ｘｙｌｙｌｃａｒｂ））、フェノチオカルブ（ｆｅｎｏｔｈｉｏｃａｒｂ）、キシリルカルブ（ｘｙｌｙｌｃａｒｂ）、ベンダイオカルブ（ｂｅｎｄｉｏｃａｒｂ）等のカーバメート系化合物、 Aldicarb, bendiocarb, benfuracarb, NAC (carbaryl), carbofuran, carbosulfan, etiofencarb MC, etiofencarb MC, etiofencarb MC, etiofencarb MC, etiofencarb MC Formatenate, furathiocarb, MIPC (isoprocarb), methiocarb, mesomyl, oxamyl, pirimicarb, urropro, x Rubethcarb, XMC (3,5-xylylmethylcarbamate), alixycarb, aldoxycarb, bufencarb, butacarb, carbolate, MT Carbamate compounds such as MPMC (xylylcarb), phenothiocarb, xylylcarb, bendiocarb, etc.
　アセタミプリド（ａｃｅｔａｍｉｐｒｉｄ）、クロチアニジン（ｃｌｏｔｈｉａｎｉｄｉｎ）、ジノテフラン（ｄｉｎｏｔｅｆｕｒａｎ）、イミダクロプリド（ｉｍｉｄａｃｌｏｐｒｉｄ）、ニテンピラム（ｎｉｔｅｎｐｙｒａｍ）、チアクロプリド（ｔｈｉａｃｌｏｐｒｉｄ）、チアメトキサム（ｔｈｉａｍｅｔｈｏｘａｍ）等のネオニコチノイド系化合物、
　クロマフェノジド（ｃｈｒｏｍａｆｅｎｏｚｉｄｅ）、ハロフェノジド（ｈａｌｏｆｅｎｏｚｉｄｅ）、メトキシフェノジド（ｍｅｔｈｏｘｙｆｅｎｏｚｉｄｅ）、テブフェノジド（ｔｅｂｕｆｅｎｏｚｉｄｅ）等のジアシルヒドラジン系化合物、
　ビストリフルロン（ｂｉｓｔｒｉｆｌｕｒｏｎ）、クロルフルアズロン（ｃｈｌｏｒｆｌｕａｚｕｒｏｎ）、ジフルベンズロン（ｄｉｆｌｕｂｅｎｚｕｒｏｎ）、フルシクロクスロン（ｆｌｕｃｙｃｌｏｘｕｒｏｎ）、フルフェノクスロン（ｆｌｕｆｅｎｏｘｕｒｏｎ）、ヘキサフルムロン（ｈｅｘａｆｌｕｍｕｒｏｎ）、ルフェヌロン（ｌｕｆｅｎｕｒｏｎ）、ノバルロン（ｎｏｖａｌｕｒｏｎ）、ノビフルムロン（ｎｏｖｉｆｌｕｍｕｒｏｎ）、テフルベンズロン（ｔｅｆｌｕｂｅｎｚｕｒｏｎ）、トリフルムロン（ｔｒｉｆｌｕｍｕｒｏｎ）等のベンゾイルウレア系化合物、
　フェノキシカルブ（ｆｅｎｏｘｙｃａｒｂ）、ヒドロプレン（ｈｙｄｒｏｐｒｅｎｅ）、キノプレン（ｋｉｎｏｐｒｅｎｅ）、メソプレン（ｍｅｔｈｏｐｒｅｎｅ）、ピリプロキシフェン（ｐｙｒｉｐｒｏｘｙｆｅｎ）、メトプレン（ｍｅｔｈｏｐｒｅｎｅ）、ハイドロプレン（ｈｙｄｒｏｐｒｅｎｅ）等の幼若ホルモン系化合物、
　クロルデン（ｃｈｌｏｒｄａｎｅ）、エンドスルファン（ｅｎｄｏｓｕｌｆａｎ）、リンデン（ｌｉｎｄａｎｅ（ｇａｍｍａ－ＨＣＨ））、ジエノクロル（ｄｉｅｎｏｃｈｌｏｒ）等のシクロジエン有機塩素系化合物、
　カルタップ塩酸塩（Ｃａｒｔａｐ　ｈｙｄｒｏｃｈｌｏｒｉｄｅ）、チオシクラム（ｔｈｉｏｃｙｃｌａｍ）等の２－ジメチルアミノプロパン－１，３－ジチオール系化合物、
　アミトラズ（ａｍｉｔｒａｚ）等のアミジン系化合物、
　エチプロール（ｅｔｈｉｐｒｏｌｅ）、フィプロニル（ｆｉｐｒｏｎｉｌ）、アセトプロール（ａｃｅｔｏｐｒｏｌｅ）等のフェニルピラゾール系化合物、
アゾシクロチン（ａｚｏｃｙｃｌｏｔｉｎ）、シヘキサチン（ｃｙｈｅｘａｔｉｎ）、酸化フェンブタスズ（フェンブタチンオキシド）（ｆｅｎｂｕｔａｔｉｎ　ｏｘｉｄｅ）等の有機スズ系化合物、
　フェナザキン（ｆｅｎａｚａｑｕｉｎ）、フェンピロキシメート（ｆｅｎｐｙｒｏｘｉｍａｔｅ）、ピリダベン（ｐｙｒｉｄａｂｅｎ）、ピリミジフェン（ｐｙｌｉｍｉｄｉｆｅｎ）、テブフェンピラド（ｔｅｂｕｆｅｎｐｙｒａｄ）、トルフェンピラド（ｔｏｌｆｅｎｐｙｒａｄ）等のＭＥＴＩ系化合物、
ブロモプロピレート（ｂｒｏｍｏｐｒｏｐｙｌａｔｅ）等のベンジレート系化合物、
　クロルフェナピル（ｃｈｌｏｒｆｅｎａｐｙｌ）等のアリルピロール系化合物、
　ＤＮＯＣ、ビナパクリル（ｂｉｎａｐａｃｒｙｌ）等のジニトロフェノール系化合物、
　クロラントラニリプロール（ｃｈｌｏｒａｎｔｒａｎｉｌｉｐｒｏｌｅ）、シアントラニリプロール（ｃｙａｎｔｒａｎｉｌｉｐｒｏｌｅ）等のアントラニル・ジアミド系化合物、
　インドキサカルブ（ｉｎｄｏｘａｃａｒｂ）等のオキサジアジン系化合物、メタフルミゾン（ｍｅｔａｆｌｕｍｉｚｏｎｅ）等のセミカルバゾン系化合物、
　スピロジクロフェン（ｓｐｉｒｏｄｉｃｌｏｆｅｎ）、スピロメシフェン（ｓｐｉｒｏｍｅｓｉｆｅｎ）、スピロテトラマト（ｓｐｉｒｏｔｅｔｒａｍａｔ）等のテトロン酸系化合物、
　トリアザメート（ｔｒｉａｚａｍａｔｅ）等のカルバモイルトリアゾール系化合物、
　ジフロビダジン（ｄｉｆｌｏｖｉｄａｚｉｎ）等のテトラジン系化合物、 Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprio, thiamethoxam, thiamethoxam
Diacylhydrazine compounds such as chromafenozide, halofenozide, methoxyphenozide, tebufenozide, and the like;
Bistrifluron, chlorfluazuuron, diflubenzuron, flucycloxuron, flufenoxuron, hexafluururon, hexafluururon ), Benzoylurea compounds such as noviflumuron, teflubenzuron, triflumuron,
Phenoxycarb, hydroprene, quinoprene, methoprene, pyriproxyfen, methoprene, hydroprene, young juvenile hormone, etc.
Cyclodiene organochlorine compounds such as chlordane, endosulfan, lindane (gamma-HCH), dienochlor, and the like;
2-dimethylaminopropane-1,3-dithiol compounds such as Cartap hydrochloride, thiocyclam,
Amidine-based compounds such as amitraz;
Phenylpyrazole compounds such as etiprole, fipronil, acetoprole, etc.,
Organotin compounds such as azocyclotin, cyhexatin, fenbutatin oxide, and the like,
METI compounds such as fenazaquin, fenpyroximate, pyridaben, pyrimidifene, tebufenpyrad, tolfenpyrad, etc.
Benzylate compounds such as bromopropyrate,
Allylpyrrole compounds such as chlorfenapyl,
Dinitrophenol compounds such as DNOC and binapacryl;
Anthranyl diamide compounds such as chlorantaniprole and cyantraniprole,
Oxadiazine compounds such as indoxacarb, semicarbazone compounds such as metaflumizone,
Tetronic acid compounds such as spirodiclofen, spiromesifen, and spirotetramat;
Carbamoyltriazole compounds such as triazamate,
Tetrazine compounds such as diflovidazin,
　アバメクチン（ａｂａｍｅｃｔｉｎ）、エマメクチン安息香酸塩（ｅｍａｍｅｃｔｉｎ　ｂｅｎｚｏａｔｅ）、ミルベメクチン（ｍｉｌｂｅｍｅｃｔｉｎ）、レピメクチン（ｌｅｐｉｍｅｃｔｉｎ）、アセキノシル（ａｃｅｑｕｉｎｏｃｙｌ）、アザジラクチン（ａｚａｄｉｒａｃｈｔｉｎ）、ベンスルタップ（ｂｅｎｓｕｌｔａｐ）、ベンゾキシメート（Ｂｅｎｚｏｘｉｍａｔｅ）、ビフェナゼート（ｂｉｆｅｎａｚａｔｅ）、ブプロフェジン（ｂｕｐｒｏｆｅｚｉｎ）、ＣＧＡ－５０４３９、キノメチオネート（ｃｈｉｎｏｍｅｔｈｉｏｎａｔ）、クロフェンテジン（ｃｌｏｆｅｎｔｅｚｉｎｅ）、クリオライト（ｃｒｙｏｌｉｔｅ）、シロマジン（ｃｙｒｏｍａｚｉｎｅ）、ダゾメット（ｄａｚｏｍｅｔ）、ＤＣＩＰ、ＤＤＴ、ジアフェンチウロン（ｄｉａｆｅｎｔｈｉｕｒｏｎ）、Ｄ－Ｄ（１，３－ジクロロプロパン（１，３－Ｄｉｃｈｌｏｒｏｐｒｏｐｅｎｅ））、ジコホール（ｄｉｃｏｆｏｌ）、ジシクラニル（ｄｉｃｙｃｌａｎｉｌ）、ジノブトン（ｄｉｎｏｂｕｔｏｎ）、ジノカップ（ｄｉｎｏｃａｐ）、ＥＮＴ　８１８４、エトキサゾール（ｅｔｏｘａｚｏｌｅ）、フロニカミド（ｆｌｏｎｉｃａｍｉｄ）、フルアクリピリム（ｆｌｕａｃｒｙｐｙｒｉｍ）、フルベンジアミド（ｆｌｕｂｅｎｄｉａｍｉｄｅ）、ＧＹ－８１（ペルオキソカルボナート）、ヘキシチアゾクス（ｈｅｘｙｔｈｉａｚｏｘ）、ヒドラメチルノン（ｈｙｄｒａｍｅｔｈｙｌｎｏｎ）、シアン化水素（Ｈｙｄｒｏｇｅｎ　ｃｙａｎｉｄｅ）、ヨウ化メチル（ｍｅｔｈｙｌ　ｉｏｄｉｄｅ）、カランジン（ｋａｒａｎｊｉｎ）、ＭＢ－５９９（ｖｅｒｂｕｔｉｎ）、塩化水銀（ｍｅｒｃｕｒｙ　ｃｈｌｏｒｉｄｅ）、メタム（ｍｅｔａｍ）、メトキシクロール（ｍｅｔｈｏｘｙｃｈｌｏｒ）、メチルイソチオシアネート（ｍｅｔｈｙｌ　ｉｓｏｔｈｉｏｃｙａｎａｔｅ）、ペンタクロロフェノール（ｐｅｎｔａｃｈｌｏｒｏｐｈｅｎｏｌ）、ホスフィン（ｐｈｏｓｐｈｉｎｅ）、ピペロニル　ブトキシド（ｐｉｐｅｒｏｎｙｌ　ｂｕｔｏｘｉｄｅ）、ポリナクチン複合体（ｐｏｌｙｎａｃｔｉｎｓ）、ＢＰＰＳ（プロパルギット（ｐｒｏｐａｒｇｉｔｅ））、ピメトロジン（ｐｙｍｅｔｒｏｚｉｎｅ）、ピレトリン（ｐｙｒｅｔｈｒｉｎｓ）、ピリダリル（ｐｙｒｉｄａｌｙｌ）、ロテノン（ｒｏｔｅｎｏｎｅ）、Ｓ４２１（ビス（２，３，３，３－テトラクロロプロピル）エーテル）、サバディラ（ｓａｂａｄｉｌｌａ）、スピノサド（ｓｐｉｎｏｓａｄ）、スピネトラム（ｓｐｉｎｅｔｏｒａｍ）、スルコフロン塩（スルコフロン－ナトリウム（ｓｕｌｃｏｆｕｒｏｎ－ｓｏｄｉｕｍ））、スルフルラミド（ｓｕｌｆｌｕｒａｍｉｄ）、テトラジホン（ｔｅｔｒａｄｉｆｏｎ）、チオスルタップ（ｔｈｉｏｓｕｌｔａｐ）、トリブホス（Ｔｒｉｂｕｆｏｓ）、アルドリン（ａｌｄｒｉｎ）、アミジチオオン（ａｍｉｄｉｔｈｉｏｎ）、アミドチオエート（ａｍｉｄｏｔｈｉｏａｔｅ）、アミノカルブ（ａｍｉｎｏｃａｒｂ）、アミトン（ａｍｉｔｏｎ）、アラマイト（ａｒａｍｉｔｅ）、アチダチオン（ａｔｈｉｄａｔｈｉｏｎ）、アゾトエート（ａｚｏｔｈｏａｔｅ）、ポリスルフィドバリウム（ｂａｒｉｕｍ　ｐｏｌｙｓｕｌｐｈｉｄｅ）、Ｂａｙｅｒ　２２４０８、Ｂａｙｅｒ　３２３９４、ベンクロチアズ（ｂｅｎｃｌｏｔｈｉａｚ）、５－（１，３－ベンゾジオキソール－５－イル）－３－ヘキシルシクロヘキサ－２－エノン、１，１－ビス（４－クロロフェニル）－２－エトキシエタノール、ブトネート（ｂｕｔｏｎａｔｅ）、ブトピロノキシル（ｂｕｔｏｐｙｒｏｎｏｘｙｌ）、２－（２－ブトキシエトキシ）エチル　チオシアナート、カンフェクロル（ｃａｍｐｈｅｃｈｌｏｒ）、クロルベンシド（ｃｈｌｏｒｂｅｎｓｉｄｅ）、クロルデコン（ｃｈｌｏｒｄｅｃｏｎｅ）、クロルジメホルム（ｃｈｌｏｒｄｉｍｅｆｏｒｍ）、クロルフェネトール（ｃｈｌｏｒｆｅｎｅｔｈｏｌ）、クロルフェンソン（ｃｈｌｏｒｆｅｎｓｏｎ）、イソプロチオラン（ｉｓｏｐｒｏｔｈｉｏｌａｎｅ）、フルアズロン（ｆｌｕａｚｕｒｏｎ）、メタアルデヒド（ｍｅｔａｌｄｅｈｙｄｅ）、フェニソブロモレート（ｐｈｅｎｉｓｏｂｒｏｍｏｌａｔｅ）、フルアジナム（ｆｌｕａｚｉｎａｍ）、ビアラホス（ｂｉａｌａｐｈｏｓ）、ベノミル（ｂｅｎｏｍｙｌ）、塩酸レバミゾール（ｌｅｖａｍｉｓｏｌ）、ピリフルキナゾン（ｐｙｒｉｆｌｕｑｕｉｎａｚｏｎ）、シフルメトフェン（ｃｙｆｌｕｍｅｔｏｆｅｎ）、アミドフルメト（ａｍｉｄｏｆｌｕｍｅｔ）、ＩＫＡ－２００５、シエノピラフェン（ｃｙｅｎｏｐｙｒａｆｅｎ）（ＮＣ５１２）、スルホキサフロール（ｓｕｌｆｏｘａｆｌｏｒ）、ピラフルプロール（ｐｙｒａｆｌｕｐｒｏｌｅ）（Ｖ３０３９）、ピリプロール（ｐｙｒｉｐｒｏｌｅ）（Ｖ３０８６）、トラロピリル（ｔｒａｌｏｐｙｒｉｌ）、フルピラゾフォス（ｆｌｕｐｙｒａｚｏｆｏｓ）、ジオフェノラン（ｄｉｏｆｅｎｏｌａｎ）、クロルベンジレート（ｃｈｌｏｒｏｂｅｎｚｉｌａｔｅ）、フルフェンジン（ｆｌｕｆｅｎｚｉｎｅ）、ベンゾメート（ｂｅｎｚｏｍａｔｅ）、フルフェネリム（ｆｌｕｆｅｎｅｒｉｍ）、Ｔｒｉｐｒｏｐｙｌ　ｉｓｏｃｙａｎｕｒａｔｅ（ＴＰＩＣ）、アルベンダゾール（ａｌｂｅｎｄａｚｏｌｅ）、オキシベンダゾール（ｏｘｉｂｅｎｄａｚｏｌｅ）、フェンベンダゾール（ｆｅｎｂｅｎｄａｚｏｌｅ）、メタム・ナトリウム（ｍｅｔａｍ－ｓｏｄｉｕｍ）、１，３－ジクロロプロペン（１，３－ｄｉｃｈｌｏｒｏｐｒｏｐｅｎｅ）、フルピラジフロン（ｆｌｕｐｙｒａｄｉｆｕｒｏｎｅ）、アフィドピロペン（ａｆｉｄｏｐｙｒｏｐｅｎ）、フロメトキン（ｆｌｏｍｅｔｏｑｕｉｎ）、ピフルブミド（ｐｙｆｌｕｂｕｍｉｄｅ）、フルエンスルホン（ｆｌｕｅｎｓｕｌｆｏｎｅ））、ＩＫＩ－３１０６、等の殺虫剤、殺ダニ剤、殺線虫剤、 Abamectin, emamectin benzoate, milbemectin, lepimectin, acequinocyl, azaziractin, benzotrope Buprofezin, CGA-50439, quinomethionate, clofentezine, cryolite, cyromazine, dazomet, DIPD, DIPD Dienthiuron, DD (1,3-dichloropropane), dicophor, dicyclanil, dinobuton, dinocap, entzol 8eto ), Flonicamid, fluacrylpyrim, flubenamide, GY-81 (peroxocarbonate), hexythiazox, hydramethylnonhydrogen. iodide , Caranjin, MB-599 (verbutin), mercuric chloride, metham, methoxychlor, methyl isothiocyanate, pentachlorophenol (pentachlorophosphine) , Piperonyl butoxide, polynactin complex, BPPS (propargite), pymetrozine, pyrethrins, pyridyl (roS), pyridalyl (2,3,3,3-tetrachloropropyl) ether), sabadilla, spinosad, spinetoram, sulcofuron salt (sulcofuron-sodium), sulfluramide, tetradiphone (Tetradifon), thiosultap, tribufos, aldrin, amidithione, amidethioate, aminocarb, amiton, amit Azotoate ), Polysulfide barium, Bayer 22408, Bayer 32394, benclothiaz, 5- (1,3-benzodioxol-5-yl) -3-hexylcyclohex-2-enone, 1,1 -Bis (4-chlorophenyl) -2-ethoxyethanol, butonate, butopyronoxyl, 2- (2-butoxyethoxy) ethyl thiocyanate, camphechlor, chlorbenside, chlordecone, chlordecone (Chlordiform), chlorphenetol, black Fenson, isoprothiolane, fluazuron, methaldehyde, phenisobromate, fluazinam, valamifos, valamiphos, melamine Pyrifluquinazone, cyflumetofen, amideflumet, IKA-2005, cienopyrafen (NC512), suloxafurolp e) (V3039), pyriprole (V3086), tralopyril, flupyrazofos, diophenolan, chlorbenzilate, flufenzimine, flufenzimine , Tripropyl isocyanate (TPIC), albendazole, oxybendazole, fenbendazole, metham-sodium, 1,3-dichloropropene (1,3-dichloropropene) ene), Furupirajifuron (flupyradifurone), Afidopiropen (afidopyropen), Furometokin (flometoquin), Pifurubumido (pyflubumide), full-toluenesulfonic (fluensulfone)), IKI-3106, pesticides and the like, miticides, nematicides,
　アゾキシストルビン（ａｚｏｘｙｓｔｒｏｂｉｎ）、クレソキシムメチル（ｋｒｅｓｏｘｙｍ－ｍｅｔｈｙｌ）、トリフロキシストロビン（ｔｒｉｆｌｏｘｙｓｔｒｏｂｉｎ）、メトミノストロビン（ｍｅｔｏｍｉｎｏｓｔｒｏｂｉｎ）、オリサストロビン（ｏｒｙｓａｓｔｒｏｂｉｎ）等のストロビルリン系化合物、
メパニピリム（ｍｅｐａｎｉｐｙｒｉｍ）、ピリメサニル（ｐｙｒｉｍｅｔｈａｎｉｌ）、シプロジニル（ｃｙｐｒｏｄｉｎｉｌ）等のアニリノピリミジン系化合物、
トリアジメホン（ｔｒｉａｄｉｍｅｆｏｎ）、ビテルタノール（ｂｉｔｅｒｔａｎｏｌ）、トリフルミゾール（ｔｒｉｆｌｕｍｉｚｏｌｅ）、メトコナゾール（ｍｅｔｏｃｏｎａｚｏｌｅ）、プロピコナゾール（ｐｒｏｐｉｃｏｎａｚｏｌｅ）、ペンコナゾール（ｐｅｎｃｏｎａｚｏｌｅ）、フルシラゾール（ｆｌｕｓｉｌａｚｏｌｅ）、ミクロブタニル（ｍｙｃｌｏｂｕｔａｎｉｌ）、シプロコナゾール（ｃｙｐｒｏｃｏｎａｚｏｌｅ）、テブコナゾール（ｔｅｂｕｃｏｎａｚｏｌｅ）、ヘキサコナゾール（ｈｅｘａｃｏｎａｚｏｌｅ）、プロクロラズ（ｐｒｏｃｈｌｏｒａｚ）、シメコナゾール（ｓｉｍｅｃｏｎａｚｏｌｅ）等のアゾール系化合物、
　キノメチオネート（ｑｕｉｎｏｍｅｔｈｉｏｎａｔｅ）等のキノキサリン系化合物、
　マンネブ（ｍａｎｅｂ）、ジネブ（ｚｉｎｅｂ）、マンコゼブ（ｍａｎｃｏｚｅｂ）、ポリカーバメート（ｐｏｌｙｃａｒｂａｍａｔｅ）、プロビネブ（ｐｒｏｐｉｎｅｂ）等のジチオカーバメート系化合物、
　ジエトフェンカルブ（ｄｉｅｔｈｏｆｅｎｃａｒｂ）等のフェニルカーバメート系化合物、
　クロロタロニル（ｃｈｌｏｒｏｔｈａｌｏｎｉｌ）、キントゼン（ｑｕｉｎｔｏｚｅｎｅ）等の有機塩素系化合物、
　ベノミル（ｂｅｎｏｍｙｌ）、チオファネートメチル（ｔｈｉｏｐｈａｎａｔｅ－ｍｅｔｈｙｌ）、カーベンダジム（ｃａｒｂｅｎｄａｚｏｌｅ）等のベンズイミダゾール系化合物、
　メタラキシル（ｍｅｔａｌａｘｙｌ）、オキサジキシル（ｏｘａｄｉｘｙｌ）、オフラセ（ｏｆｕｒａｓｅ）、ベナラキシル（ｂｅｎａｌａｘｙｌ）、フララキシル（ｆｕｒａｌａｘｙｌ）、シプロフラン（ｃｙｐｒｏｆｕｒａｍ）等のフェニルアミド系化合物、
　ジクロフルアニド（ｄｉｃｈｌｏｆｌｕａｎｉｄ）等のスルフェン酸系化合物、
　水酸化第二銅（ｃｏｐｐｅｒ　ｈｙｄｒｏｘｉｄｅ）、オキシキノリン銅（ｏｘｉｎｅ－ｃｏｐｐｅｒ）等の銅系化合物、
　ヒドロキシイソキサゾール（ｈｙｄｒｏｘｙｉｓｏｘａｚｏｌｅ）等のイソキサゾール系化合物、
　ホセチルアルミニウム（ｆｏｓｅｔｙｌ－ａｌｕｍｉｎｉｕｍ）、トルクロホス－メチル（ｔｏｌｃｌｏｆｏｓ－ｍｅｔｈｙｌ）等の有機リン系化合物、
　キャプタン（ｃａｐｔａｎ）、カプタホール（ｃａｐｔａｆｏｌ）、フォルペット（ｆｏｌｐｅｔ）等のＮ－ハロゲノチオアルキル系化合物、
　プロシミドン（ｐｒｏｃｙｍｉｄｏｎｅ）、イプロジオン（ｉｐｒｏｄｉｏｎｅ）、ビンクロゾリン（ｖｉｎｃｈｌｏｚｏｌｉｎ）等のジカルボキシイミド系化合物、
　フルトラニル（ｆｌｕｔｏｌａｎｉｌ）、メプロニル（ｍｅｐｒｏｎｉｌ）、フラメトピル（ｆｕｒａｍｅｐｙｒ）、チフルザミド（ｔｈｉｆｌｕｚａｍｉｄｅ）、ボスカリド（ｂｏｓｃａｌｉｄ）、ペンチオピラド（ｐｅｎｔｈｉｏｐｙｒａｄ）等のカルボキシアニリド系化合物、
　フェンプロピモルフ（ｆｅｎｐｒｏｐｉｍｏｒｐｈ）、ジメトモルフ（ｄｉｍｅｔｈｏｍｏｒｐｈ）等のモルフォリン系化合物、
　水酸化トリフェニルスズ（ｆｅｎｔｈｉｎ　ｈｙｄｒｏｘｉｄｅ）、酢酸トリフェニルスズ（ｆｅｎｔｈｉｎ　ａｃｅｔａｔｅ）等の有機スズ系化合物、
　フルジオキソニル（ｆｌｕｄｉｏｘｏｎｉｌ）、フェンピクロニル（ｆｅｎｐｉｃｌｏｎｉｌ）等のシアノピロール系化合物、 Strobilurin-based compounds such as azoxystrobin, cresoxime-methyl, trifloxystrobin, methminostrobin, oryastrostrobin
Anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil, etc.,
Triadimefone, bittertanol, triflumizole, metconazole, propiconazole, microconil, penconazole, fluconazole, penconazole, fluconazole. Azole compounds such as tebuconazole, hexaconazole, prochloraz, and simeconazole,
Quinoxaline compounds such as quinomethionate,
Dithiocarbamate compounds such as manneb, zineb, mancozeb, polycarbamate, and propineb,
Phenyl carbamate compounds such as dietofencarb,
Organochlorine compounds such as chlorothalonil and quintozen,
Benzimidazole compounds such as benomyl, thiophanate-methyl, carbendazole, and the like;
Phenylamide compounds such as metalaxyl, oxadixyl, ofurase, benalaxyl, furalaxyl, cyprofuram, and the like;
Sulfenic acid compounds such as dichlorfluanid,
Copper-based compounds such as cupric hydroxide and copper oxyquinoline (oxine-copper);
Isoxazole compounds such as hydroxyisoxazole,
Organophosphorus compounds such as fosetyl-aluminum, tolcrofos-methyl,
N-halogenoalkyl compounds such as captan, captafol, folpet, etc.,
Dicarboximide compounds such as procymidone, iprodione, vinclozolin, and the like;
Carboxanilide compounds such as flutolanil, mepronil, furamepyr, thifluzamide, boscalid, pentiopyrad, etc.,
Morpholine compounds such as fenpropimorph and dimethomorph,
Organotin compounds such as triphenyltin hydroxide and triphenyltin acetate,
Cyanopyrrole compounds such as fludioxonil and fenpiclonil,
　その他トリシクラゾール（ｔｒｉｃｙｃｌａｚｏｌｅ）、ピロキロン（ｐｙｒｏｑｕｉｌｏｎ）、カルプロパミド（ｃａｒｐｒｏｐａｍｉｄ）、ジクロシメット（ｄｉｃｌｏｃｙｍｅｔ）、フェノキサニル（ｆｅｎｏｘａｎｉｌ）、フサライド（ｆｔｈａｌｉｄｅ）、フルアジナム（ｆｌｕａｚｉｎａｍ）、シモキサニル（ｃｙｍｏｘａｎｉｌ）、トリホリン（ｔｒｉｆｏｒｉｎｅ）、ピリフェノックス（ｐｙｒｉｆｅｎｏｘ）、フェナリモル（ｆｅｎａｒｉｍｏｌ）、フェンプロピディン（ｆｅｎｐｒｏｐｉｄｉｎ）、ペンシクロン（ｐｅｎｃｙｃｕｒｏｎ）、フェリムゾン（ｆｅｒｉｍｚｏｎｅ）、シアゾファミド（ｃｙａｚｏｆａｍｉｄ）、イプロバリカルブ（ｉｐｒｏｖａｌｉｃａｒｂ）、ベンチアバリカルブイソプロピル（ｂｅｎｔｈｉａｖａｌｉｃａｒｂ－ｉｓｏｐｒｏｐｙｌ）、イミノクタジンアルベシル酸塩（ｉｍｉｎｏｃｔａｄｉｎ－ａｌｂｅｓｉｌａｔｅ）、シフルフェナミド（ｃｙｆｌｕｆｅｎａｍｉｄ）、カスガマイシン（ｋａｓｕｇａｍｙｃｉｎ）、バリダマイシン（ｖａｌｉｄａｍｙｃｉｎ）、ストレプトマイシン（ｓｔｒｅｐｔｏｍｙｃｉｎ）、オキソリニック酸（ｏｘｏｌｉｎｉｃ－ａｃｉｄ）、テブフロキン（ｔｅｂｕｆｌｏｑｕｉｎ）、プロベナゾール（ｐｒｏｂｅｎａｚｏｌｅ）、チアジニル（ｔｉａｄｉｎｉｌ）イソチアニル（ｉｓｏｔｉａｎｉｌ）、トルプロカルブ（ｔｏｌｐｒｏｃａｒｂ）、イソフェタミド（ｉｓｏｆｅｔａｍｉｄ）等の殺菌剤、 Others: tricyclazole, pyroquilon, carpropamide, diclocymet, phenoxanil, fthalide, fluazinomyl, fluazinamyl pyrifenox, fenarimol, fenpropidin, pencyclone, ferimzone, cyazofamid, iprovalicalb, isopropyl carb thiavalicarb-isopropyl), iminoctadin-albesylate, cyflufenamid, kasugamycin, validamycin, valetomycin, streptomycin (streptomycin) Fungicides such as (probenazole), thiazinyl (isoadinil), isothianyl (isotianil), tolprocarb (isoprotamide),
　クロルピクリン（ｃｈｌｏｒｏｐｉｃｒｉｎ）、エチレンジブロマイド（ＥＤＢ）、フッ化スルフリル（ｓｕｌｆｕｒｙｌ　ｆｌｕｏｒｉｄｅ）、アクリロニトリル（ａｃｒｙｌｏｎｉｔｒｉｌｅ）、ビス（２－クロロエチル）　エーテル、１－ブロモ－２－クロロエタン、３－ブロモ－１－クロロプロパ－１－エン、ブロモシクレン（ｂｒｏｍｏｃｙｃｌｅｎ）、二硫化炭素（ｃａｒｂｏｎ　ｄｉｓｕｌｆｉｄｅ）、四塩化炭素（ｔｅｔｒａｃｈｌｏｒｏｍｅｔｈａｎｅ）、カーバムナトリウム塩（ｍｅｔｈａｍ　ｓｏｄｉｕｍ）、ネマデクチン（ｎｅｍａｄｅｃｔｉｎ）リン化アルミニウム（ａｌｕｍｉｎｕｍ　ｐｈｏｓｐｈｉｄｅ）等のくん蒸剤、 Chlorpicrin, ethylene dibromide (EDB), sulfuryl fluoride, acrylonitrile, bis (2-chloroethyl) ether, 1-bromo-2-chloroethane, 3-bromo-1-chloroprop-1 -Ene, bromocyclen, carbon disulfide, carbon tetrachloride, carbam sodium salt, nemadectin, aluminum phosphide, etc.
　バチルス・チューリンゲンシス　デルタ　エンドトキシン（Ｂａｃｉｌｌｕｓ　ｔｈｕｒｉｎｇｉｅｎｓｉｓ　ｄｅｌｔａ－ｅｎｄｏｔｏｘｉｎ）、ボラックス（ｂｏｒａｘ）、カルシウム　ポリスルフィド（ｃａｌｃｉｕｍ　ｐｏｌｙｓｕｌｆｉｄｅ）、クリオライト（ｃｒｙｏｌｉｔｅ）、サイトカイニン（ｃｙｔｏｋｉｎｉｎ）、ニコチン（ｎｉｃｏｔｉｎｅ）、２－（オクチルチオ）エタノール、オレイン酸カリウム（ｐｏｔａｓｓｉｕｍ　ｏｌｅａｔｅ）、オレイン酸ナトリウム（ｓｏｄｉｕｍ　ｏｌｅａｔｅ）、マシン油（ｍａｃｈｉｎｅ　ｏｉｌ）、硫黄（ｓｕｌｆｕｒ）、タール油（ｔａｒ　ｏｉｌ）、アナバシン（ａｎａｂａｓｉｎｅ）、酒石酸モランテル（ｍｏｒａｎｔｅｌ　ｔａｒｔｒａｔｅ）、除虫菊（ピレトリン（ｐｙｒｅｔｈｒｕｍ））、硫酸ニコチン（ｎｉｃｏｔｉｎｅ　ｓｕｌｆａｔｅ）、ナタネ油（ｒａｐｅ　ｓｅｅｄ　ｏｉｌ）、ダイズレチシン（ｓｏｙｂｅａｎ　ｌｅｃｉｔｈｉｎ）、デンプン（ｓｔａｒｃｈ）、ヒドロキシプロピルデンプン（ｈｙｄｒｏｘｙｐｒｏｐｙｌｓｔａｒｃｈ）、脂肪酸グリセリド（ｄｅｃａｎｏｙｌｏｃｔａｎｏｙｌｇｌｙｃｅｒｏｌ）、プロピレングリコールモノ脂肪酸エステル（ｐｒｏｐｙｌｅｎｅ　ｇｌｙｃｏｌ　ｆａｔｔｙ　ａｃｉｄ　ｅｓｔｅｒ）、ケイソウ土（ｄｉａｔｏｍｉｔｅ）、バチルス・チューリンゲンシス（Ｂａｃｉｌｌｕｓ　ｔｈｕｒｉｎｇｉｅｎｓｉｓ）等の天然物化合物、 Bacillus thuringiensis delta endotoxin (Bacillus thuringiensis delta-endotoxin), borax, calcium polysulfide, cryolite, cytokinin, thiotinin, ethanol Potassium oleate, sodium oleate, machine oil, sulfur, tar oil, anabasine, morantel tartrate, insecticide (Pyrethrum), nicotine sulfate, rapeseed oil, soybean reticin, starch, hydroxypropyl starch, fatty acid glycol (decylolglycol) natural product compounds such as propylene glycol fatty acid ester, diatomite, Bacillus thuringiensis,
　さらに、下記一般式（ＡＡ）で表される化合物およびその塩、下記式（ＢＢ）で表される化合物、下記一般式（ＣＣ）で表される化合物、下記一般式（ＤＤ）で表される化合物、下記一般式（ＥＥ）で表される化合物等が挙げられる。下記式中のＣ１～Ｃ６アルキル基等の置換基の定義は、本発明化合物の置換基Ｒ１、Ｒ２、Ｒ５、Ｈｙで説明したＣ１～Ｃ６アルキル基等の定義と同様である。
　一般式（ＡＡ）で表される化合物は以下の通りである。 Furthermore, the compound represented by the following general formula (AA) and a salt thereof, the compound represented by the following formula (BB), the compound represented by the following general formula (CC), and the following general formula (DD) Examples thereof include compounds and compounds represented by the following general formula (EE). The definition of substituents such as C1 to C6 alkyl groups in the following formula is the same as the definition of C1 to C6 alkyl groups and the like described for the substituents R 1 , R 2 , R 5 and Hy of the compound of the present invention.
The compound represented by general formula (AA) is as follows.
Figure JPOXMLDOC01-appb-C000069
Figure JPOXMLDOC01-appb-C000069
　一般式（ＡＡ）中、Ｒａ１は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基を示し、Ｒａ２は、水素原子、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基を表し、Ｒａ６は、式Ｃ－Ｒａ３で表される基又は窒素原子を表す。
　Ｒａ３及びＲａ４は、それぞれ独立して、水素原子、ハロゲン原子、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ７シクロアルキル基、シアノ基、置換されていてもよいフェニル基、置換されていてもよいヘテロシクリル基、置換されていてもよいフェノキシ基を表す。
　（ＢＢ）で表される化合物は以下の通りである。 In general formula (AA), R a1 represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group, and R a2 represents a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C2 to C6 alkenyl group. R a6 represents a group represented by the formula C—R a3 or a nitrogen atom.
R a3 and R a4 each independently represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C7 cycloalkyl group, a cyano group, an optionally substituted phenyl group, a substituted Represents an optionally substituted heterocyclyl group, and an optionally substituted phenoxy group.
The compounds represented by (BB) are as follows.
Figure JPOXMLDOC01-appb-C000070
Figure JPOXMLDOC01-appb-C000070
　一般式（ＣＣ）で表される化合物は以下の通りである。 The compounds represented by the general formula (CC) are as follows.
Figure JPOXMLDOC01-appb-C000071
Figure JPOXMLDOC01-appb-C000071
　一般式（ＣＣ）中、Ｒｃ１は、置換されていてもよいピリジル基、置換されていてもよいチアゾリル基を表し、Ｙｃ１は、ハロゲン原子、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルコキシ基を表し、Ｙｃ２は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルコキシ基、置換されていてもよいフェニル基を表し、ｎｃは０～４の整数を表し、ｍｃは０～５の整数を表す。ｎｃが２～４の場合、Ｙｃ１はそれぞれ同じでも異なっていてもよく、ｍｃが２～５の場合、Ｙｃ２はそれぞれ同じでも異なっていてもよい。
　一般式（ＤＤ）で表される化合物は以下の通りである。 In the general formula (CC), R c1 represents an optionally substituted pyridyl group or an optionally substituted thiazolyl group, and Y c1 represents a halogen atom, a C1 to C6 alkyl group, or a C1 to C6 alkoxy group. represents, Y c2 represents a halogen atom, a cyano group, C 1 ~ C 6 alkyl group, C 1 ~ C 6 alkoxy group, a phenyl group which may be substituted, n c represents an integer of 0 to 4, m c represents an integer of 0 to 5. When n c is 2 to 4, Y c1 may be the same or different, and when m c is 2 to 5, Y c2 may be the same or different.
The compound represented by general formula (DD) is as follows.
Figure JPOXMLDOC01-appb-C000072
Figure JPOXMLDOC01-appb-C000072
　一般式（ＤＤ）中、Ｒｄ１は、置換されていてもよいフェニル基、置換されていてもよいヘテロシクリル基を表し、Ｒｄ２、Ｒｄ３はそれぞれ独立して、水素原子、Ｃ１～Ｃ６アルキル基を表し、Ｒｄ４、Ｒｄ５はそれぞれ独立して、ハロゲン原子、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基を表し、Ｒｄ６はＣ１～Ｃ６ハロアルキル基を表し、Ｙｄはハロゲン原子、シアノ基を表し、ｎｄは１～４の整数を表す。ｎｄが２～４の場合、Ｙｄはそれぞれ同じでも異なっていてもよい。
　一般式（ＥＥ）で表される化合物は以下の通りである。 In general formula (DD), R d1 represents an optionally substituted phenyl group or an optionally substituted heterocyclyl group, and R d2 and R d3 each independently represent a hydrogen atom or a C1-C6 alkyl group. R d4 and R d5 each independently represents a halogen atom, a C1 to C6 alkyl group or a C1 to C6 haloalkyl group, R d6 represents a C1 to C6 haloalkyl group, Y d represents a halogen atom or a cyano group the stands, n d represents an integer of 1-4. When n d is 2 to 4, Y d may be the same or different.
The compound represented by general formula (EE) is as follows.
Figure JPOXMLDOC01-appb-C000073
Figure JPOXMLDOC01-appb-C000073
　一般式（ＥＥ）中、Ｒｅ１、Ｒｅ２、Ｒｅ３、Ｒｅ４は、それぞれ独立して、水素原子、ハロゲン原子、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、置換されていてもよいフェニル基、Ｙｅ１、Ｙｅ２は、それぞれ独立してハロゲン原子、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルコキシ基を表し、ｎｅは０～５の整数を表し、ｍｅは０～４の整数を表す。　ｎｅが２～５の場合、Ｙｅ１はそれぞれ同じでも異なっていてもよく、ｍｅが２～４の場合、Ｙｅ２はそれぞれ同じでも異なっていてもよい。
　上記に挙げた化合物の中には立体異性体をとりうる化合物もあるが、本発明にはこれら異性体も含まれる。 In general formula (EE), R e1 , R e2 , R e3 , and R e4 each independently represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or an optionally substituted phenyl. group, Y e1, Y e2 each independently represents a halogen atom, C1 ~ C6 alkyl group, a C1 ~ C6 alkoxy group, n e represents an integer of 0 to 5, an integer of m e is 0-4 To express. When n e is 2 to 5, Y e1 may be the same or different, and when m e is 2 to 4, Y e2 may be the same or different.
Some of the compounds listed above can take stereoisomers, but these isomers are also included in the present invention.
　本発明化合物と他の殺虫剤及び／又は殺菌剤との混合物における、本発明化合物と他の殺虫剤及び／又は殺菌剤の混合割合は、特に限定されないが、例えば、本発明化合物：他の殺虫剤及び／又は殺菌剤が、０．０１：１００～１００：０．０１、又は０．１：１００～１００：０．１、又は１：１００～１００：１、又は１：１０～１０：１、又は１：１（何れも重量換算）である。 The mixing ratio of the compound of the present invention and other insecticides and / or fungicides in the mixture of the compound of the present invention and other insecticides and / or fungicides is not particularly limited. For example, the compound of the present invention: other insecticides Agent and / or fungicide is 0.01: 100 to 100: 0.01, or 0.1: 100 to 100: 0.1, or 1: 100 to 100: 1, or 1:10 to 10: 1. Or 1: 1 (both in terms of weight).
　次の実施例により本発明の代表的な実施例を説明するが、本発明はこれらに限定されるものではない。
　なお、本実施例において合成する本発明化合物及び参考化合物の詳細については、化合物番号と共に、後に示す第５表～第８表に記載する。 The following examples explain typical examples of the present invention, but the present invention is not limited thereto.
The details of the compound of the present invention and the reference compound synthesized in this example are described in Tables 5 to 8 shown below together with the compound numbers.
［実施例］
（参考例１）
－参考化合物（化合物番号：Ａ－０３５）の合成－
　段階１：１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン [Example]
(Reference Example 1)
-Synthesis of Reference Compound (Compound No .: A-035)-
Step 1: 1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone
Figure JPOXMLDOC01-appb-C000074
Figure JPOXMLDOC01-appb-C000074
　チオニコチンアミド（６．５０　ｇ，　４７．０　ｍｍｏｌ）のエタノール溶液（５０ｍＬ）にクロロアセチルアセトン（１５．８　ｇ，　１１８　ｍｍｏｌ）を加え、還流下にて８時間攪拌した。冷却後、形成された沈殿物を吸引ろ過し、エタノールおよび酢酸エチルで洗浄し、減圧条件下で乾燥させた。得られた固体を炭酸カリウム水溶液に徐々に加え、酢酸エチルにて抽出を行った。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルター濾過した。溶媒を減圧留去し、目的物　（８．４２　ｇ）を収率８２％で得た。
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　９．１９　（１Ｈ，　ｓ），　８．７１　（１Ｈ，　ｓ），　８．２８　（１Ｈ，　ｄ，　Ｊ　＝　８．０　Ｈｚ），　７．４２　（１Ｈ，　ｄｄ，　Ｊ　＝　８．０，　４．９　Ｈｚ），　２．８１　（３Ｈ，　ｓ），　２．６０　（３Ｈ，　ｓ）． Chloroacetylacetone (15.8 g, 118 mmol) was added to an ethanol solution (50 mL) of thionicotinamide (6.50 g, 47.0 mmol), and the mixture was stirred for 8 hours under reflux. After cooling, the formed precipitate was filtered off with suction, washed with ethanol and ethyl acetate and dried under reduced pressure. The obtained solid was gradually added to an aqueous potassium carbonate solution and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was filtered. The solvent was distilled off under reduced pressure to obtain the desired product (8.42 g) in a yield of 82%.
1 H-NMR (CDCl 3 ) δ: 9.19 (1H, s), 8.71 (1H, s), 8.28 (1H, d, J = 8.0 Hz), 7.42 (1H, dd, J = 8.0, 4.9 Hz), 2.81 (3H, s), 2.60 (3H, s).
　段階２：１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　オキシム Stage 2: 1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone oxime
Figure JPOXMLDOC01-appb-C000075
Figure JPOXMLDOC01-appb-C000075
　１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン（２．００ｇ，９．１６　ｍｍｏｌ）のエタノール溶液（２０　ｍＬ）にヒドロキシルアミン５０％水溶液（２．４２　ｇ，３６．６　ｍｍｏｌ）を加え、還流下にて３時間攪拌した。反応溶液に水を加え、室温まで冷却した後、得られた白色固体をろ過した。得られた白色固体を減圧乾燥させた後、目的化合物（２．１４ｇ）を収率９５％で得た。
１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　１１．５６　（１Ｈ，　ｓ），　９．０９　（１Ｈ，　ｄ，　Ｊ　＝　１．５　Ｈｚ），　８．６６　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．７　Ｈｚ），　８．２７　（１Ｈ，　ｄｔ，　Ｊ　＝　８．１，　２．０　Ｈｚ），　７．５３　（１Ｈ，　ｄｄ，　Ｊ　＝　８．０，　４．９　Ｈｚ），　２．５９　（３Ｈ，　ｓ），　２．２５　（３Ｈ，　ｓ）． 1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone (2.00 g, 9.16 mmol) in ethanol (20 mL) was added 50% aqueous hydroxylamine (2.42). g, 36.6 mmol) was added, and the mixture was stirred under reflux for 3 hours. Water was added to the reaction solution, and after cooling to room temperature, the resulting white solid was filtered. The obtained white solid was dried under reduced pressure, and then the target compound (2.14 g) was obtained with a yield of 95%.
1 H-NMR (DMSO-D 6 ) δ: 11.56 (1H, s), 9.09 (1H, d, J = 1.5 Hz), 8.66 (1H, dd, J = 4.7) , 1.7 Hz), 8.27 (1H, dt, J = 8.1, 2.0 Hz), 7.53 (1H, dd, J = 8.0, 4.9 Hz), 2.59 (3H, s), 2.25 (3H, s).
　段階３：１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　Ｏ－ピリミジン－２－イル　オキシム化合物（化合物番号：Ａ－０３５） Stage 3: 1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone O-pyrimidin-2-yl oxime compound (compound number: A-035)
Figure JPOXMLDOC01-appb-C000076
Figure JPOXMLDOC01-appb-C000076
　１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　オキシム　（１．２０　ｇ，　５．１４　ｍｍｏｌ）のＮ，Ｎ－ジメチルホルムアミド溶液（１０　ｍＬ）に炭酸カリウム（２．１３　ｇ，１５．４　ｍｍｏｌ）および２－ブロモピリミジン（１．６４　ｇ，１０．３　ｍｍｏｌ）を加え、８０℃にて３時間攪拌した。反応溶液に水を加え、酢酸エチルにて抽出を行った。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、得られた固体をジイソプロピルエーテルで洗浄し、目的物（１．３７　ｇ）を収率８６％で得た。
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　９．１６　（１Ｈ，　ｔ，　Ｊ　＝　１．２　Ｈｚ），　８．６８－８．６６　（３Ｈ，　ｍ），　８．２４　（１Ｈ，　ｄｔ，　Ｊ　＝　８．１，　２．０　Ｈｚ），　７．４１－７．３８　（１Ｈ，　ｍ），　７．１１　（１Ｈ，　ｔ，　Ｊ　＝　４．６　Ｈｚ），　２．７６　（３Ｈ，　ｓ），　２．６２　（３Ｈ，　ｓ）． 1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone oxime (1.20 g, 5.14 mmol) in N, N-dimethylformamide solution (10 mL) in potassium carbonate (2.13 g, 15.4 mmol) and 2-bromopyrimidine (1.64 g, 10.3 mmol) were added, and the mixture was stirred at 80 ° C. for 3 hours. Water was added to the reaction solution, and extraction was performed with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the resulting solid was washed with diisopropyl ether to obtain the desired product (1.37 g) in a yield of 86%.
1 H-NMR (CDCl 3 ) δ: 9.16 (1H, t, J = 1.2 Hz), 8.68-8.66 (3H, m), 8.24 (1H, dt, J = 8 .1, 2.0 Hz), 7.41-7.38 (1H, m), 7.11 (1H, t, J = 4.6 Hz), 2.76 (3H, s), 2.62 (3H, s).
（参考例２）
－参考化合物（化合物番号：Ａ－０５６）の合成－
　段階１：１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）プロパン－１－オン (Reference Example 2)
-Synthesis of Reference Compound (Compound No .: A-056)-
Step 1: 1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) propan-1-one
Figure JPOXMLDOC01-appb-C000077
Figure JPOXMLDOC01-appb-C000077
　Ｎ－メトキシ－Ｎ，４－ジメチル－２－（ピリジン－３－イル）チアゾール－５－カルボキシアミド（２．００　ｇ，　７．６０　ｍｍｏｌ）のテトラヒドロフラン溶液（５０ｍＬ）を－７８℃に冷却し、１ｍｏｌ／Ｌエチルマグネシウムブロミドのテトラヒドロフラン溶液（９．９　ｍＬ，　９．９　ｍｍｏｌ）を加えた。０℃まで徐々に昇温し、０℃で２時間攪拌した。反応溶液に飽和塩化アンモニウム水溶液を加え、酢酸エチルにて抽出を行い、飽和食塩水で洗浄した。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、シリカゲルクロマトグラフィー（ヘキサン／酢酸エチル＝１）にて精製を行い、目的化合物（０．４０　ｇ）を収率２２％で得た。
　１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　９．１８　（１Ｈ，　ｄｄ，　Ｊ　＝　２．３，　０．９　Ｈｚ），　８．７３　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．５　Ｈｚ），　８．３７　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．０，　２．３，　１．５　Ｈｚ），　７．５８　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．０，　４．７，　０．９　Ｈｚ），　２．９９　（２Ｈ，　ｑ，　Ｊ　＝　７．０　Ｈｚ），　２．７４　（３Ｈ，　ｓ），　１．１０　（３Ｈ，　ｔ，　Ｊ　＝　７．０　Ｈｚ）． A tetrahydrofuran solution (50 mL) of N-methoxy-N, 4-dimethyl-2- (pyridin-3-yl) thiazole-5-carboxamide (2.00 g, 7.60 mmol) was cooled to −78 ° C., A 1 mol / L ethylmagnesium bromide tetrahydrofuran solution (9.9 mL, 9.9 mmol) was added. The temperature was gradually raised to 0 ° C., and the mixture was stirred at 0 ° C. for 2 hours. A saturated aqueous ammonium chloride solution was added to the reaction solution, extracted with ethyl acetate, and washed with saturated brine. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (hexane / ethyl acetate = 1) to obtain the target compound (0.40 g) in a yield of 22%.
1 H-NMR (DMSO-D 6 ) δ: 9.18 (1H, dd, J = 2.3, 0.9 Hz), 8.73 (1H, dd, J = 4.7, 1.5 Hz) ), 8.37 (1H, ddd, J = 8.0, 2.3, 1.5 Hz), 7.58 (1H, ddd, J = 8.0, 4.7, 0.9 Hz), 2.99 (2H, q, J = 7.0 Hz), 2.74 (3H, s), 1.10 (3H, t, J = 7.0 Hz).
　段階２：１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）プロパン－１－オン　オキシム Stage 2: 1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) propan-1-one oxime
Figure JPOXMLDOC01-appb-C000078
Figure JPOXMLDOC01-appb-C000078
　１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）プロパン－１－オン（０．４０　ｇ，　１．７　ｍｍｏｌ）のエタノール溶液（５　ｍＬ）にヒドロキシルアミン５０％水溶液（０．４５　ｇ，　６．８　ｍｍｏｌ）を加え、還流下にて１０時間攪拌した。室温まで冷却した後、析出した固体をろ過、ジイソプロピルエーテルで洗浄し、目的化合物（０．２０　ｇ）を収率４８％で得た。
　１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　１１．５５　（１Ｈ，　ｓ），　９．１０　（１Ｈ，　ｄｄ，　Ｊ　＝　２．５，　０．８　Ｈｚ），　８．６７　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．７　Ｈｚ），　８．２８　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．０，　２．５，　１．７　Ｈｚ），　７．５４　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．０，　４．７，　０．８　Ｈｚ），　２．７２　（２Ｈ，　ｑ，　Ｊ　＝　７．６　Ｈｚ），　２．５７　（３Ｈ，　ｓ），　１．１１　（３Ｈ，　ｔ，　Ｊ　＝　７．６　Ｈｚ）． Hydroxylamine 50% in an ethanol solution (5 mL) of 1- (4-methyl-2- (pyridin-3-yl) thiazol-5-yl) propan-1-one (0.40 g, 1.7 mmol) Aqueous solution (0.45 g, 6.8 mmol) was added and stirred under reflux for 10 hours. After cooling to room temperature, the precipitated solid was filtered and washed with diisopropyl ether to obtain the target compound (0.20 g) in a yield of 48%.
1 H-NMR (DMSO-D 6 ) δ: 11.55 (1H, s), 9.10 (1H, dd, J = 2.5, 0.8 Hz), 8.67 (1H, dd, J = 4.7, 1.7 Hz), 8.28 (1H, ddd, J = 8.0, 2.5, 1.7 Hz), 7.54 (1H, ddd, J = 8.0, 4 .7, 0.8 Hz), 2.72 (2H, q, J = 7.6 Hz), 2.57 (3H, s), 1.11 (3H, t, J = 7.6 Hz).
　段階３：１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）プロパン－１－オン　Ｏ－ピリミジン－２－イル　オキシム　化合物（化合物番号：Ａ－０５６） Stage 3: 1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) propan-1-one O-pyrimidin-2-yl oxime compound (compound number: A-056)
Figure JPOXMLDOC01-appb-C000079
Figure JPOXMLDOC01-appb-C000079
　１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）プロパン－１－オン（０．２０　ｇ，　０．８１　ｍｍｏｌ）のＮ，Ｎ－ジメチルホルムアミド溶液（５ｍＬ）に炭酸カリウム（０．１７　ｇ，　１．２　ｍｍｏｌ）および２－ブロモピリミジン（０．１９　ｇ，　１．２　ｍｍｏｌ）を加え、８０℃にて１２時間攪拌した。反応溶液に水を加え、酢酸エチルにて抽出を行い、飽和食塩水で洗浄した。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、得られた固体をシリカゲルクロマトグラフィー（酢酸エチル）にて精製を行い、目的化合物（０．０５　ｇ）を収率１９％で得た。
　１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　９．１６　（１Ｈ，　ｍ），　８．７４　（２Ｈ，　ｄ，　Ｊ　＝　４．６　Ｈｚ），　８．７１－８．６９　（１Ｈ，　ｍ），　８．３５－８．３３　（１Ｈ，　ｍ），　７．５８－７．５６　（１Ｈ，　ｍ），　７．３３　（１Ｈ，　ｔ，　Ｊ　＝　４．６　Ｈｚ），　２．９５　（２Ｈ，　ｑ，　Ｊ　＝　７．５　Ｈｚ），　２．７２　（３Ｈ，　ｓ），　１．２４　（３Ｈ，　ｔ，　Ｊ　＝　７．５　Ｈｚ）． To a solution of 1- (4-methyl-2- (pyridin-3-yl) thiazol-5-yl) propan-1-one (0.20 g, 0.81 mmol) in N, N-dimethylformamide (5 mL) Potassium carbonate (0.17 g, 1.2 mmol) and 2-bromopyrimidine (0.19 g, 1.2 mmol) were added, and the mixture was stirred at 80 ° C. for 12 hours. Water was added to the reaction solution, extracted with ethyl acetate, and washed with saturated brine. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the obtained solid was purified by silica gel chromatography (ethyl acetate) to obtain the target compound (0.05 g) in a yield of 19%.
1 H-NMR (DMSO-D 6 ) δ: 9.16 (1H, m), 8.74 (2H, d, J = 4.6 Hz), 8.71-8.69 (1H, m), 8.35-8.33 (1H, m), 7.58-7.56 (1H, m), 7.33 (1H, t, J = 4.6 Hz), 2.95 (2H, q, J = 7.5 Hz), 2.72 (3H, s), 1.24 (3H, t, J = 7.5 Hz).
（実施例１）
－本発明化合物（化合物番号：Ａ－００１）の合成－
　段階１：１－（２－（ピリジン－３－イル）チアゾール－５－イル）エタノンの (Example 1)
-Synthesis of the compound of the present invention (Compound No .: A-001)-
Step 1: 1- (2- (Pyridin-3-yl) thiazol-5-yl) ethanone
Figure JPOXMLDOC01-appb-C000080
Figure JPOXMLDOC01-appb-C000080
　チオニコチンアミド（２．００　ｇ，　１４．５　ｍｍｏｌ）にＮ，Ｎ－ジメチルホルムアミド　ジメチルアセタール（３．４５　ｇ，　２９．０　ｍｍｏｌ）を加え、室温下にて２時間攪拌した。減圧下にて低沸点成分を留去した後、エタノール（２０　ｍＬ）、ブロモアセトン（２．９７　ｇ，　２１．７　ｍｍｏｌ）を加え、室温下にて４時間攪拌した。生成した固形物をろ過し、得られた母液に炭酸カリウム水溶液を加え、酢酸エチルにて抽出を行った。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、得られた固体をシリカゲルクロマトグラフィー（ヘキサン／酢酸エチル＝３→１）にて精製を行い。目的化合物（０．８３　ｇ）を収率２８％で得た。
　１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　９．２３　（１Ｈ，　ｄ，　Ｊ　＝　１．８　Ｈｚ），　８．７７　（１Ｈ，　ｓ），　８．７５－８．７４　（１Ｈ，　ｍ），　８．４２－８．４０　（１Ｈ，　ｍ），　７．６１－７．５８　（１Ｈ，　ｍ），　２．６４　（３Ｈ，　ｓ）． N, N-dimethylformamide dimethylacetal (3.45 g, 29.0 mmol) was added to thionicotinamide (2.00 g, 14.5 mmol), and the mixture was stirred at room temperature for 2 hours. After distilling off low-boiling components under reduced pressure, ethanol (20 mL) and bromoacetone (2.97 g, 21.7 mmol) were added, and the mixture was stirred at room temperature for 4 hours. The produced solid was filtered, an aqueous potassium carbonate solution was added to the obtained mother liquor, and extraction was performed with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the resulting solid was purified by silica gel chromatography (hexane / ethyl acetate = 3 → 1). The target compound (0.83 g) was obtained with a yield of 28%.
1 H-NMR (DMSO-D 6 ) δ: 9.23 (1H, d, J = 1.8 Hz), 8.77 (1H, s), 8.75-8.74 (1H, m), 8.42-8.40 (1H, m), 7.61-7.58 (1H, m), 2.64 (3H, s).
　段階２：１－（２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　Ｏ－メチル　オキシム化合物（化合物番号：Ａ－００１） Stage 2: 1- (2- (Pyridin-3-yl) thiazol-5-yl) ethanone O-methyl oxime compound (Compound No .: A-001)
Figure JPOXMLDOC01-appb-C000081
Figure JPOXMLDOC01-appb-C000081
　１－（２－（ピリジン－３－イル）チアゾール－５－イル）エタノン（０．４０　ｇ，２．０　ｍｍｏｌ）のエタノール溶液（５　ｍＬ）にＯ－メチルヒドロキシルアミン塩酸塩（０．６５　ｇ，７．８　ｍｍｏｌ）を加え、還流下にて３時間攪拌した。反応溶液に水を加え、減圧下にてエタノールを留去した。炭酸カリウム水溶液を加え、酢酸エチルにて抽出を行った。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、得られた固体をシリカゲルクロマトグラフィー（ヘキサン／酢酸エチル＝３）にて精製を行い、目的化合物（０．３９　ｇ）を収率８５％で得た。
　ｍａｊｏｒ：１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　９．１９－９．１６　（１Ｈ，　ｍ），　８．７０－８．６９　（１Ｈ，　ｍ），　８．３６－８．３３　（１Ｈ，　ｍ），　８．３０　（１Ｈ，　ｓ），　７．５６　（１Ｈ，　ｍ），　３．９３　（３Ｈ，　ｓ），　　２．２７　（３Ｈ，　ｓ）．
　ｍｉｎｏｒ：１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　９．１９－９．１６　（１Ｈ，　ｍ），　８．７０－８．６９　（１Ｈ，　ｍ），　８．４７　（１Ｈ，　ｓ），　８．３６－８．３３　（１Ｈ，　ｍ），　７．５６　（１Ｈ，　ｍ），　４．００　（３Ｈ，　ｓ），　２．３６　（３Ｈ，　ｓ）． 1- (2- (Pyridin-3-yl) thiazol-5-yl) ethanone (0.40 g, 2.0 mmol) in ethanol (5 mL) was added O-methylhydroxylamine hydrochloride (0.65 g). , 7.8 mmol), and stirred under reflux for 3 hours. Water was added to the reaction solution, and ethanol was distilled off under reduced pressure. A potassium carbonate aqueous solution was added, and extraction was performed with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the resulting solid was purified by silica gel chromatography (hexane / ethyl acetate = 3) to obtain the desired compound (0.39 g) in a yield of 85%.
major: 1 H-NMR (DMSO-D 6 ) δ: 9.19-9.16 (1H, m), 8.70-8.69 (1H, m), 8.36-8.33 (1H, m), 8.30 (1H, s), 7.56 (1H, m), 3.93 (3H, s), 2.27 (3H, s).
minor: 1 H-NMR (DMSO-D 6 ) δ: 9.19-9.16 (1H, m), 8.70-8.69 (1H, m), 8.47 (1H, s), 8 .36-8.33 (1H, m), 7.56 (1H, m), 4.00 (3H, s), 2.36 (3H, s).
（実施例２）
－本発明化合物（化合物番号：Ｃ－００９）の合成－
　段階１：１－（２，３’－ビピリジン－５－イル）エタノン (Example 2)
-Synthesis of the compound of the present invention (Compound No .: C-009)-
Step 1: 1- (2,3′-bipyridin-5-yl) ethanone
Figure JPOXMLDOC01-appb-C000082
Figure JPOXMLDOC01-appb-C000082
　１－（６－ブロモピリジン－３－イル）エタノン（１．００　ｇ，　５．０　ｍｍｏｌ）、炭酸カリウム（３．７６　ｇ，　２０．０　ｍｍｏｌ）、ピリジン－３－イルボロン酸（１．２３　ｇ，　１０．０　ｍｍｏｌ）のジメトキシエタン溶液（１３　ｍＬ）に水（６．５　ｍＬ）を加えた。反応溶液にテトラキス（トリフェニルホスフィン）パラジウム（０）（０．２９　ｇ，　０．２５　ｍｏｌ）を加え、窒素置換を行った後、８５℃にて３時間攪拌した。反応溶液に酢酸エチルを加え、炭酸カリウム水溶液で３回洗浄した。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、得られた固体をジイソプロピルエーテルおよび酢酸エチルで洗浄し、目的物（０．４５　ｇ）を収率４６％で得た。
　１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　９．３６－９．３５　（１Ｈ，　ｍ），　９．２５－９．２４　（１Ｈ，　ｍ），　８．７０　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．７　Ｈｚ），　８．５３　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．０，　２．４，　１．８　Ｈｚ），　８．４１　（１Ｈ，　ｄｄ，　Ｊ　＝　８．３，　２．４　Ｈｚ），　８．２５　（１Ｈ，　ｄｄ，　Ｊ　＝　８．３，　０．９　Ｈｚ），　７．５９－７．５７　（１Ｈ，　ｍ），　２．６８　（３Ｈ，　ｓ）． 1- (6-Bromopyridin-3-yl) ethanone (1.00 g, 5.0 mmol), potassium carbonate (3.76 g, 20.0 mmol), pyridin-3-ylboronic acid (1.23 g , 10.0 mmol) in dimethoxyethane (13 mL) was added water (6.5 mL). Tetrakis (triphenylphosphine) palladium (0) (0.29 g, 0.25 mol) was added to the reaction solution, and after nitrogen substitution, the mixture was stirred at 85 ° C. for 3 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed 3 times with an aqueous potassium carbonate solution. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the resulting solid was washed with diisopropyl ether and ethyl acetate to obtain the desired product (0.45 g) in a yield of 46%.
1 H-NMR (DMSO-D 6 ) δ: 9.36-9.35 (1H, m), 9.25-9.24 (1H, m), 8.70 (1H, dd, J = 4. 7, 1.7 Hz), 8.53 (1H, ddd, J = 8.0, 2.4, 1.8 Hz), 8.41 (1H, dd, J = 8.3, 2.4 Hz) ), 8.25 (1H, dd, J = 8.3, 0.9 Hz), 7.59-7.57 (1H, m), 2.68 (3H, s).
　段階２：１－（２，３’－ビピリジン－５－イル）エタノン　オキシム Stage 2: 1- (2,3'-bipyridin-5-yl) ethanone oxime
Figure JPOXMLDOC01-appb-C000083
Figure JPOXMLDOC01-appb-C000083
　１－（２，３’－ビピリジン－５－イル）エタノン（０．２０　ｇ，１．０１　ｍｍｏｌ）のエタノール溶液（５　ｍＬ）にヒドロキシルアミン５０％水溶液（０．２７　ｇ，４．０４　ｍｍｏｌ）を加え、還流下にて３時間攪拌した。反応溶液に水を加え、室温まで冷却した後、得られた白色固体をろ過した。得られた白色固体を減圧乾燥させた後、目的化合物（０．１５　ｇ）を収率７０％で得た。
　１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　１１．５７　（１Ｈ，　ｓ），　９．４－９．２　（１Ｈ，　ｍ），　９．０－８．８　（１Ｈ，　ｍ），　８．６５　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．７　Ｈｚ），　８．４８－８．４６　（１Ｈ，　ｍ），　８．１５　（１Ｈ，　ｄｄ，　Ｊ　＝　８．３，　２．４　Ｈｚ），　８．１０　（１Ｈ，　ｄｄ，　Ｊ　＝　８．６，　０．９　Ｈｚ），　７．５４　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．０，　４．８，　０．８　Ｈｚ），　２．２３　（３Ｈ，　ｓ）． Hydroxylamine 50% aqueous solution (0.27 g, 4.04 mmol) in ethanol solution (5 mL) of 1- (2,3′-bipyridin-5-yl) ethanone (0.20 g, 1.01 mmol) And stirred under reflux for 3 hours. Water was added to the reaction solution, and after cooling to room temperature, the resulting white solid was filtered. The obtained white solid was dried under reduced pressure, and then the target compound (0.15 g) was obtained with a yield of 70%.
1 H-NMR (DMSO-D 6 ) δ: 11.57 (1H, s), 9.4-9.2 (1H, m), 9.0-8.8 (1H, m), 8.65 (1H, dd, J = 4.7, 1.7 Hz), 8.48-8.46 (1H, m), 8.15 (1H, dd, J = 8.3, 2.4 Hz), 8.10 (1H, dd, J = 8.6, 0.9 Hz), 7.54 (1H, ddd, J = 8.0, 4.8, 0.8 Hz), 2.23 (3H, s).
　段階３：１－（２，３’－ビピリジン－４－イル）エタノン　Ｏ－ピリミジン－２－イル　オキシム　化合物　オキシム化合物（化合物番号：Ｃ－００９） Stage 3: 1- (2,3'-bipyridin-4-yl) ethanone O-pyrimidin-2-yl oxime compound oxime compound (compound number: C-009)
Figure JPOXMLDOC01-appb-C000084
Figure JPOXMLDOC01-appb-C000084
　１－（２，３’－ビピリジン－５－イル）エタノン　オキシム　（０．１０　ｇ，　０．４７　ｍｍｏｌ）のＮ，Ｎ－ジメチルホルムアミド溶液（３　ｍＬ）に炭酸カリウム（０．２０　ｇ，１．４　ｍｍｏｌ）および２－ブロモピリミジン（０．１５　ｇ，０．９４　ｍｍｏｌ）を加え、８０℃にて３時間攪拌した。反応溶液に水を加え、酢酸エチルにて抽出を行った。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、得られた固体をジイソプロピルエーテルで洗浄し、目的物（０．７８　ｇ）を収率５４％で得た。
　１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　９．３４　（１Ｈ，　ｄ，　Ｊ　＝　２．４　Ｈｚ），　９．１１　（１Ｈ，　ｄ，　Ｊ　＝　２．１　Ｈｚ），　８．７４　（２Ｈ，　ｄ，　Ｊ　＝　４．９　Ｈｚ），　８．６８　（１Ｈ，　ｄｄ，　Ｊ　＝　４．９，　１．５　Ｈｚ），　８．５１　（１Ｈ，　ｄｔ，　Ｊ　＝　８．１，　２．０　Ｈｚ），　８．３４　（１Ｈ，　ｄｄ，　Ｊ　＝　８．３，　２．４　Ｈｚ），　８．２１　（１Ｈ，　ｄ，　Ｊ　＝　８．３　Ｈｚ），　７．５７　（１Ｈ，　ｄｄ，　Ｊ　＝　８．０，　４．９　Ｈｚ），　７．３４　（１Ｈ，　ｔ，　Ｊ　＝　４．７　Ｈｚ），　２．５５　（３Ｈ，　ｓ）． To a solution of 1- (2,3′-bipyridin-5-yl) ethanone oxime (0.10 g, 0.47 mmol) in N, N-dimethylformamide (3 mL) was added potassium carbonate (0.20 g, 1. 4 mmol) and 2-bromopyrimidine (0.15 g, 0.94 mmol) were added, and the mixture was stirred at 80 ° C. for 3 hours. Water was added to the reaction solution, and extraction was performed with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the resulting solid was washed with diisopropyl ether to obtain the desired product (0.78 g) in a yield of 54%.
1 H-NMR (DMSO-D 6 ) δ: 9.34 (1H, d, J = 2.4 Hz), 9.11 (1H, d, J = 2.1 Hz), 8.74 (2H, d, J = 4.9 Hz), 8.68 (1H, dd, J = 4.9, 1.5 Hz), 8.51 (1H, dt, J = 8.1, 2.0 Hz), 8.34 (1H, dd, J = 8.3, 2.4 Hz), 8.21 (1H, d, J = 8.3 Hz), 7.57 (1H, dd, J = 8.0, 4.9 Hz), 7.34 (1H, t, J = 4.7 Hz), 2.55 (3H, s).
（実施例３）
－本発明化合物（化合物番号：Ｃ－００３）の合成－
　段階１：１－（５－（ピリジン－３－イル）チアゾール－２－イル）エタノン (Example 3)
-Synthesis of the compound of the present invention (Compound No .: C-003)-
Step 1: 1- (5- (Pyridin-3-yl) thiazol-2-yl) ethanone
Figure JPOXMLDOC01-appb-C000085
Figure JPOXMLDOC01-appb-C000085
　３－ブロモピリジン（３．００　ｇ，１９．０　ｍｍｏｌ）、１－（チアゾール－２－イル）エタノン（４．８３　ｇ，３８．０　ｍｍｏｌ）のＮ，Ｎ－ジメチルアセトアミド溶液（２０　ｍＬ）に酢酸カリウム（３．７３　ｇ，　３８．０　ｍｍｏｌ）およびアリル　１，４－ビス（ジフェニルホスフィノ）ブタン　パラジウム（ＩＩ）クロリド（１．３６　ｇ，　１．１０　ｍｍｏｌ）を加え、窒素置換した後、１５０℃にて２０時間攪拌した。反応溶液に水を加え、酢酸エチルにて抽出を行った。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、得られた固体をシリカゲルクロマトグラフィー（ヘキサン／酢酸エチル＝１）にて精製を行い。目的化合物（０．７５　ｇ）を収率１９％で得た。
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　８．９２　（１Ｈ，　ｄ，　Ｊ　＝　１．８　Ｈｚ），　８．６６　（１Ｈ，　ｄｄ，　Ｊ　＝　４．９，　１．５　Ｈｚ），　８．１９　（１Ｈ，　ｓ），　７．９３－７．９１　（１Ｈ，　ｍ），　７．４１　（１Ｈ，　ｄｄ，　Ｊ　＝　７．６，　４．３　Ｈｚ），　２．７４　（３Ｈ，　ｓ）． To a solution of 3-bromopyridine (3.00 g, 19.0 mmol), 1- (thiazol-2-yl) ethanone (4.83 g, 38.0 mmol) in N, N-dimethylacetamide (20 mL). Potassium acetate (3.73 g, 38.0 mmol) and allyl 1,4-bis (diphenylphosphino) butane palladium (II) chloride (1.36 g, 1.10 mmol) were added and the atmosphere was replaced with nitrogen. The mixture was stirred at 150 ° C. for 20 hours. Water was added to the reaction solution, and extraction was performed with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the resulting solid was purified by silica gel chromatography (hexane / ethyl acetate = 1). The target compound (0.75 g) was obtained with a yield of 19%.
1 H-NMR (CDCl 3 ) δ: 8.92 (1H, d, J = 1.8 Hz), 8.66 (1H, dd, J = 4.9, 1.5 Hz), 8.19 ( 1H, s), 7.93-7.91 (1H, m), 7.41 (1H, dd, J = 7.6, 4.3 Hz), 2.74 (3H, s).
段階２：１－（５－（ピリジン－３－イル）チアゾール－２－イル）エタノン　Ｏ－メチル　オキシム　化合物（化合物番号：Ｃ－００３） Step 2: 1- (5- (pyridin-3-yl) thiazol-2-yl) ethanone O-methyl oxime compound (compound number: C-003)
Figure JPOXMLDOC01-appb-C000086
Figure JPOXMLDOC01-appb-C000086
　１－（５－（ピリジン－３－イル）チアゾール－２－イル）エタノン（０．２０ｇ，０．９８　ｍｍｏｌ）のエタノール溶液（５ｍＬ）にＯ－メチルヒドロキシルアミン塩酸塩（１．２３　ｇ，１４．５　ｍｍｏｌ）を加え、還流下にて３時間攪拌した。反応溶液に水を加え、減圧下にてエタノールを留去した。炭酸カリウム水溶液を加え、酢酸エチルにて抽出を行った。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、得られた固体をシリカゲルクロマトグラフィー（ヘキサン／酢酸エチル＝１）にて精製を行い、目的化合物（０．０９５　ｇ）を収率４１％で得た。
ｍａｊｏｒ：１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　８．８６　（１Ｈ，　ｄ，　Ｊ　＝　１．１　Ｈｚ），　８．５９　（１Ｈ，　ｄｄ，　Ｊ　＝　４．９，　１．５　Ｈｚ），　８．０２　（１Ｈ，　ｓ），　７．８６　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．０，　２．３，　１．７　Ｈｚ），　７．３９－７．３４　（１Ｈ，　ｍ），　４．０６　（３Ｈ，　ｓ），　２．３５　（３Ｈ，　ｓ）．
ｍｉｎｏｒ：１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　８．９０　（１Ｈ，　ｄ，　Ｊ　＝　１．５　Ｈｚ），　８．６１　（１Ｈ，　ｄｄ，　Ｊ　＝　４．９，　１．５　Ｈｚ），　８．１７　（１Ｈ，　ｓ），　７．９２　（１Ｈ，　ｄｔ，　Ｊ　＝　８．０，　２．０　Ｈｚ），　７．３９－７．３４　（１Ｈ，　ｍ），　４．１６　（３Ｈ，　ｓ），　２．４９　（３Ｈ，　ｓ）． O-methylhydroxylamine hydrochloride (1.23 g, 14) was added to a solution of 1- (5- (pyridin-3-yl) thiazol-2-yl) ethanone (0.20 g, 0.98 mmol) in ethanol (5 mL). 0.5 mmol) was added and stirred at reflux for 3 hours. Water was added to the reaction solution, and ethanol was distilled off under reduced pressure. A potassium carbonate aqueous solution was added, and extraction was performed with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the resulting solid was purified by silica gel chromatography (hexane / ethyl acetate = 1) to obtain the target compound (0.095 g) in a yield of 41%.
major: 1 H-NMR (CDCl 3 ) δ: 8.86 (1H, d, J = 1.1 Hz), 8.59 (1H, dd, J = 4.9, 1.5 Hz), 8. 02 (1H, s), 7.86 (1H, ddd, J = 8.0, 2.3, 1.7 Hz), 7.39-7.34 (1H, m), 4.06 (3H, s), 2.35 (3H, s).
minor: 1 H-NMR (CDCl 3 ) δ: 8.90 (1H, d, J = 1.5 Hz), 8.61 (1H, dd, J = 4.9, 1.5 Hz), 8. 17 (1H, s), 7.92 (1H, dt, J = 8.0, 2.0 Hz), 7.39-7.34 (1H, m), 4.16 (3H, s), 2 .49 (3H, s).
（実施例４）
－本発明化合物（Ａ－０６３、Ａ－０６７、Ａ－０７３）の合成－
　段階１：１－（４－（クロロメチル）－２－（ピリジン－３－イル）チアゾール－５－ｙｌ）エタノン　Ｏ－メチル　オキシム　化合物（化合物番号：Ａ－０６３） Example 4
-Synthesis of the compounds of the present invention (A-063, A-067, A-073)-
Step 1: 1- (4- (Chloromethyl) -2- (pyridin-3-yl) thiazol-5-yl) ethanone O-methyl oxime compound (Compound No: A-063)
Figure JPOXMLDOC01-appb-C000087
Figure JPOXMLDOC01-appb-C000087
　１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　Ｏ－メチル　オキシム　（２．００　ｇ，　８．１０　ｍｍｏｌ）のＮ，Ｎ－ジメチルホルムアミド溶液（１０　ｍＬ）にＮ－クロロスクシンイミド（２．１６　ｇ，　１６．２　ｍｍｏｌ）を加え、６０℃にて８時間攪拌した。反応溶液に亜硫酸ナトリウム水溶液を加え、酢酸エチルにて抽出を行った。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、得られた固体をシリカゲルクロマトグラフィー（ヘキサン／酢酸エチル＝３→１）にて精製を行い、目的化合物（１．６２　ｇ）を収率７１％で得た。
　１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　９．１４　（１Ｈ，　ｄ，　Ｊ　＝　１．８　Ｈｚ），　８．７１－８．７１　（１Ｈ，　ｍ），　８．３４－８．３２　（１Ｈ，　ｍ），　７．５７　（１Ｈ，　ｄｄ，　Ｊ　＝　８．０，　４．９　Ｈｚ），　５．０３　（２Ｈ，　ｓ），　３．９７　（３Ｈ，　ｓ），　２．３４　（３Ｈ，　ｓ）． 1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone O-methyl oxime (2.00 g, 8.10 mmol) in N, N-dimethylformamide (10 mL) N-chlorosuccinimide (2.16 g, 16.2 mmol) was added to and stirred at 60 ° C. for 8 hours. A sodium sulfite aqueous solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the resulting solid was purified by silica gel chromatography (hexane / ethyl acetate = 3 → 1) to obtain the target compound (1.62 g) in a yield of 71%.
1 H-NMR (DMSO-D 6 ) δ: 9.14 (1H, d, J = 1.8 Hz), 8.71-8.71 (1H, m), 8.34-8.32 (1H M), 7.57 (1H, dd, J = 8.0, 4.9 Hz), 5.03 (2H, s), 3.97 (3H, s), 2.34 (3H, s) .
　段階２：１－（４－（エチルチオメチル）－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　Ｏ－メチル　オキシム　化合物（化合物番号：Ａ－０６７） Stage 2: 1- (4- (Ethylthiomethyl) -2- (pyridin-3-yl) thiazol-5-yl) ethanone O-methyl oxime compound (compound number: A-067)
Figure JPOXMLDOC01-appb-C000088
Figure JPOXMLDOC01-appb-C000088
　１－（４－（クロロメチル）－２－（ピリジン－３－イル）チアゾール－５－ｙｌ）エタノン　Ｏ－メチル　オキシム（０．４０　ｇ，　１．４　ｍｍｏｌ）のＮ，Ｎ－ジメチルホルムアミド溶液（５ｍＬ）にナトリウム　エタンチオレート（０．２４　ｇ，　２．８　ｍｍｏｌ）を加え、５０℃にて３時間攪拌した。反応溶液に水を加え、酢酸エチルにて抽出を行った。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、得られた固体をシリカゲルクロマトグラフィー（ヘキサン／酢酸エチル／＝１）にて精製を行い。目的化合物（０．３５　ｇ）を収率８０％で得た。
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　９．１４　（１Ｈ，　ｄ，　Ｊ　＝　１．５　Ｈｚ），　８．６５　（１Ｈ，　ｄｄ，　Ｊ　＝　４．９，　１．５　Ｈｚ），　８．２２　（１Ｈ，　ｄｔ，　Ｊ　＝　８．３，　２．０　Ｈｚ），　７．３８　（１Ｈ，　ｄｄ，　Ｊ　＝　７．６，　５．１　Ｈｚ），　４．１３　（２Ｈ，　ｓ），　４．０２　（３Ｈ，　ｓ），　２．６９　（２Ｈ，　ｑ，　Ｊ　＝　７．３　Ｈｚ），　２．３１　（３Ｈ，　ｓ），　１．３２　（３Ｈ，　ｔ，　Ｊ　＝　７．３　Ｈｚ）． 1- (4- (Chloromethyl) -2- (pyridin-3-yl) thiazol-5-yl) ethanone O-methyl oxime (0.40 g, 1.4 mmol) in N, N-dimethylformamide solution ( Sodium ethanethiolate (0.24 g, 2.8 mmol) was added to 5 mL), and the mixture was stirred at 50 ° C. for 3 hours. Water was added to the reaction solution, and extraction was performed with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the resulting solid was purified by silica gel chromatography (hexane / ethyl acetate / = 1). The target compound (0.35 g) was obtained with a yield of 80%.
1 H-NMR (CDCl 3) δ: 9.14 (1H, d, J = 1.5 Hz), 8.65 (1H, dd, J = 4.9, 1.5 Hz), 8.22 (1H , Dt, J = 8.3, 2.0 Hz), 7.38 (1H, dd, J = 7.6, 5.1 Hz), 4.13 (2H, s), 4.02 (3H, s), 2.69 (2H, q, J = 7.3 Hz), 2.31 (3H, s), 1.32 (3H, t, J = 7.3 Hz).
段階３：３－（４－（エチルスルホニルメチル）－５－（１－（メトキシイミノ）エチル）チアゾール－２－イル）ピリジン　１－オキシド　化合物（化合物番号：Ａ－０７３） Step 3: 3- (4- (Ethylsulfonylmethyl) -5- (1- (methoxyimino) ethyl) thiazol-2-yl) pyridine 1-oxide compound (Compound number: A-073)
Figure JPOXMLDOC01-appb-C000089
Figure JPOXMLDOC01-appb-C000089
　１－（４－（エチルチオメチル）－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　Ｏ－メチル　オキシム　（０．２５　ｇ，　０．８２　ｍｍｏｌ）のジクロロメタン溶液（５　ｍＬ）にメタクロロ過安息香酸７０％品（０．６１　ｇ，　２．５　ｍｍｏｌ）を加え、室温にて１８時間攪拌した。反応溶液に亜硫酸ナトリウム水溶液を加え、ジクロロメタンにて抽出を行った後、炭酸カリウム水溶液で洗浄した。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、得られた固体をシリカゲルクロマトグラフィー（ヘキサン／酢酸エチル＝３→１）にて精製を行い、目的化合物（０．１９　ｇ）を収率６８％で得た。
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　８．８０　（１Ｈ，　ｓ），　８．２５　（１Ｈ，　ｄ，　Ｊ　＝　６．７　Ｈｚ），　７．７０　（１Ｈ，　ｄ，　Ｊ　＝　８．０　Ｈｚ），　７．３８－７．３７　（１Ｈ，　ｍ），　４．８４　（２Ｈ，　ｓ），　４．０４　（３Ｈ，　ｓ），　３．１９　（２Ｈ，　ｑ，　Ｊ　＝　７．４　Ｈｚ），　２．３２　（３Ｈ，　ｓ），　１．４７　（４Ｈ，　ｔ，　Ｊ　＝　７．５　Ｈｚ）．　 To a dichloromethane solution (5 mL) of 1- (4- (ethylthiomethyl) -2- (pyridin-3-yl) thiazol-5-yl) ethanone O-methyl oxime (0.25 g, 0.82 mmol) A 70% product of metachloroperbenzoic acid (0.61 g, 2.5 mmol) was added, and the mixture was stirred at room temperature for 18 hours. A sodium sulfite aqueous solution was added to the reaction solution, extracted with dichloromethane, and then washed with an aqueous potassium carbonate solution. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the resulting solid was purified by silica gel chromatography (hexane / ethyl acetate = 3 → 1) to obtain the target compound (0.19 g) in a yield of 68%.
1 H-NMR (CDCl 3 ) δ: 8.80 (1H, s), 8.25 (1H, d, J = 6.7 Hz), 7.70 (1H, d, J = 8.0 Hz) , 7.38-7.37 (1H, m), 4.84 (2H, s), 4.04 (3H, s), 3.19 (2H, q, J = 7.4 Hz), 32 (3H, s), 1.47 (4H, t, J = 7.5 Hz).
（実施例５）
－本発明化合物（化合物番号：Ａ－０２１）の合成－
　１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　Ｏ－エチルカルバモイル　オキシム　化合物（化合物番号：Ａ－０２１） (Example 5)
-Synthesis of the compound of the present invention (Compound No. A-021)-
1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone O-ethylcarbamoyl oxime compound (Compound No .: A-021)
Figure JPOXMLDOC01-appb-C000090
Figure JPOXMLDOC01-appb-C000090
　１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　オキシム　（０．２０　ｇ，　０．８６　ｍｍｏｌ）のテトラヒドロフラン溶液（５　ｍＬ）にマグネシウムブロミドジエチルエーテル錯体（０．２９　ｇ，　１．１　ｍｍｏｌ）およびエチルイソシアネート（７９　μＬ，　１．１　ｍｍｏｌ）を加え、６０℃にて３時間攪拌した。反応溶液に水を加え、酢酸エチルにて抽出を行い、飽和炭酸水素ナトリウム水溶液、飽和食塩水で洗浄した。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、シリカゲルクロマトグラフィー（酢酸エチル）にて精製を行い、目的化合物（０．１４　ｇ）を収率５３％で得た。
　１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　９．１３　（１Ｈ，　ｄｄ，　Ｊ　＝　２．１，　０．８　Ｈｚ），　８．７０　（１Ｈ，　ｄｄ，　Ｊ　＝　４．８，　１．５　Ｈｚ），　８．３２　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．０，　２．１，　１．５　Ｈｚ），　７．５６　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．０，　４．８，　０．８　Ｈｚ），　７．４７　（１Ｈ，　ｔ，　５．５　Ｈｚ），　３．１４　（２Ｈ，　ｄｑ，　Ｊ　＝　７．０，　５．５　Ｈｚ），　２．６５　（３Ｈ，　ｓ）
，２．４３（３Ｈ，　ｓ），１．０９　（３Ｈ，　ｔ，　Ｊ　＝　７．０　Ｈｚ）． A magnesium bromide diethyl ether complex (0 mL) was added to a tetrahydrofuran solution (5 mL) of 1- (4-methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone oxime (0.20 g, 0.86 mmol). .29 g, 1.1 mmol) and ethyl isocyanate (79 μL, 1.1 mmol) were added, and the mixture was stirred at 60 ° C. for 3 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, and the mixture was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and purification was performed by silica gel chromatography (ethyl acetate) to obtain the target compound (0.14 g) in a yield of 53%.
1 H-NMR (DMSO-D 6 ) δ: 9.13 (1H, dd, J = 2.1, 0.8 Hz), 8.70 (1H, dd, J = 4.8, 1.5 Hz) ), 8.32 (1H, ddd, J = 8.0, 2.1, 1.5 Hz), 7.56 (1H, ddd, J = 8.0, 4.8, 0.8 Hz), 7.47 (1H, t, 5.5 Hz), 3.14 (2H, dq, J = 7.0, 5.5 Hz), 2.65 (3H, s)
, 2.43 (3H, s), 1.09 (3H, t, J = 7.0 Hz).
（実施例６）
－本発明化合物（化合物番号：Ａ－０１６）の合成－
　１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　Ｏ－エトキシカルボニル　オキシム　化合物（化合物番号：Ａ－０１６） (Example 6)
-Synthesis of the compound of the present invention (Compound No .: A-016)-
1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone O-ethoxycarbonyl oxime compound (Compound No .: A-016)
Figure JPOXMLDOC01-appb-C000091
Figure JPOXMLDOC01-appb-C000091
　１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　オキシム　（０．２０　ｇ，　０．８６　ｍｍｏｌ）のＮ，Ｎ－ジメチルホルムアミド溶液（５　ｍＬ）に炭酸カリウム（０．３６　ｇ，　２．９　ｍｍｏｌ）およびクロロ炭酸エチル（０．２８ｇ，　２．６　ｍｍｏｌ）を加え、８０℃にて１５時間攪拌した。反応溶液に水を加え、酢酸エチルにて抽出を行い、飽和食塩水で洗浄した。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、シリカゲルクロマトグラフィー（酢酸エチル／ヘキサン＝２）にて精製を行い、目的化合物（０．０８　ｇ）を収率３０％で得た。
　１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　９．１１　（１Ｈ，　ｄｄ，　Ｊ　＝　２．３，　０．８　Ｈｚ），　８．６７　（１Ｈ，　ｄｄ，　Ｊ　＝　４．９，　１．８　Ｈｚ），　８．２９　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．３，　２．３，　１．８　Ｈｚ），　７．５４　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．３，　４．９，　０．８　Ｈｚ），　４．１８　（２Ｈ，　ｑ，　Ｊ　＝　７．０　Ｈｚ），　２．６０　（３Ｈ，　ｓ），　２．２８　（３Ｈ，　ｓ），　１．２７　（３Ｈ，　ｔ，　Ｊ　＝　７．０　Ｈｚ）． 1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone oxime (0.20 g, 0.86 mmol) in N, N-dimethylformamide (5 mL) in potassium carbonate (0.36 g, 2.9 mmol) and ethyl chlorocarbonate (0.28 g, 2.6 mmol) were added, and the mixture was stirred at 80 ° C. for 15 hours. Water was added to the reaction solution, extracted with ethyl acetate, and washed with saturated brine. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate / hexane = 2) to obtain the target compound (0.08 g) in a yield of 30%.
1 H-NMR (DMSO-D 6 ) δ: 9.11 (1H, dd, J = 2.3, 0.8 Hz), 8.67 (1H, dd, J = 4.9, 1.8 Hz) ), 8.29 (1H, ddd, J = 8.3, 2.3, 1.8 Hz), 7.54 (1H, ddd, J = 8.3, 4.9, 0.8 Hz), 4.18 (2H, q, J = 7.0 Hz), 2.60 (3H, s), 2.28 (3H, s), 1.27 (3H, t, J = 7.0 Hz).
（実施例７）
－本発明化合物（化合物番号：Ａ－０１２）の合成－
　１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　Ｏ－アセチル　オキシム　化合物（化合物番号：Ａ－０１２） (Example 7)
-Synthesis of the compound of the present invention (Compound No. A-012)-
1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone O-acetyl oxime compound (Compound No .: A-012)
Figure JPOXMLDOC01-appb-C000092
Figure JPOXMLDOC01-appb-C000092
　１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　オキシム　（０．２０ｇ，　０．８６　ｍｍｏｌ）のジクロロメタン溶液（５　ｍＬ）にトリエチルアミン（１６６　μＬ，　１．２９　ｍｍｏｌ）および塩化アセチル（９２　μＬ，　１．３　ｍｍｏｌ）を加え、室温にて２時間攪拌した。反応溶液に水を加え、酢酸エチルにて抽出を行い、飽和炭酸水素ナトリウム水溶液、飽和食塩水で洗浄した。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、得られた固体をジイソプロピルエーテルで洗浄し、目的物（０．１１　ｇ）を収率４９％で得た。
　１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　９．１５　（１Ｈ，　ｄｄ，　Ｊ　＝　２．３，　０．６　Ｈｚ），　８．７０　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．５　Ｈｚ），　８．３３　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．０，　２．３，　１．５　Ｈｚ），　７．５６　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．０，　４．７，　０．６　Ｈｚ），　２．６７　（３Ｈ，　ｓ），　２．４６　（３Ｈ，ｓ），　２．２４　（３Ｈ，ｓ）． Triethylamine (166 μL, 1.29) was added to a dichloromethane solution (5 mL) of 1- (4-methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone oxime (0.20 g, 0.86 mmol). mmol) and acetyl chloride (92 μL, 1.3 mmol) were added, and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, and the mixture was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the resulting solid was washed with diisopropyl ether to obtain the desired product (0.11 g) in a yield of 49%.
1 H-NMR (DMSO-D 6 ) δ: 9.15 (1H, dd, J = 2.3, 0.6 Hz), 8.70 (1H, dd, J = 4.7, 1.5 Hz) ), 8.33 (1H, ddd, J = 8.0, 2.3, 1.5 Hz), 7.56 (1H, ddd, J = 8.0, 4.7, 0.6 Hz), 2.67 (3H, s), 2.46 (3H, s), 2.24 (3H, s).
（実施例８）
－本発明化合物（化合物番号：Ａ－０２６）の合成－
　１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　Ｏ－ジメチルカルバモイル　オキシム　化合物（化合物番号：Ａ－０２６） (Example 8)
-Synthesis of the compound of the present invention (Compound No .: A-026)-
1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone O-dimethylcarbamoyl oxime compound (Compound No .: A-026)
　１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　オキシム　（０．２０　ｇ，　０．８６　ｍｍｏｌ）のＮ，Ｎ－ジメチルホルムアミド溶液（５　ｍＬ）に氷冷下６０％水素化ナトリウム（０．０５０　ｇ，　１．３　ｍｍｏｌ）を加え、３０分攪拌した。次いで、Ｎ，Ｎ－ジメチルカルバモイルクロリド（１１９　μＬ，　１．２９　ｍｍｏｌ）を加え１００℃にて１０時間攪拌した。反応溶液に水を加え、酢酸エチルにて抽出を行い、飽和炭酸水素ナトリウム水溶液、飽和食塩水で洗浄した。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、得られた固体をジイソプロピルエーテルで洗浄し、目的物（０．２０　ｇ）を収率７８％で得た。
　１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　９．１４　（１Ｈ，　ｄｄ，　Ｊ　＝　２．４，　１．０　Ｈｚ），　８．６６　（１Ｈ，　ｄｄ，　Ｊ　＝　４．９，　１．５　Ｈｚ），　８．２２　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．３，　２．４，　１．５　Ｈｚ），　７．３９　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．３，　４．９，　１．０　Ｈｚ），　３．０４　（６Ｈ，　ｓ），　２．７３　（３Ｈ，　ｓ），　２．４３　（３Ｈ，　ｓ）． 1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone oxime (0.20 g, 0.86 mmol) in N, N-dimethylformamide solution (5 mL) was ice-cooled. Under 60% sodium hydride (0.050 g, 1.3 mmol) was added and stirred for 30 minutes. Next, N, N-dimethylcarbamoyl chloride (119 μL, 1.29 mmol) was added and stirred at 100 ° C. for 10 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, and the mixture was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the resulting solid was washed with diisopropyl ether to obtain the desired product (0.20 g) in a yield of 78%.
1 H-NMR (CDCl 3 ) δ: 9.14 (1H, dd, J = 2.4, 1.0 Hz), 8.66 (1H, dd, J = 4.9, 1.5 Hz), 8.22 (1H, ddd, J = 8.3, 2.4, 1.5 Hz), 7.39 (1H, ddd, J = 8.3, 4.9, 1.0 Hz), 04 (6H, s), 2.73 (3H, s), 2.43 (3H, s).
（実施例９）
－本発明化合物（化合物番号：Ｂ－００７）の合成－
　４－メチル－２－（ピリジン－３－イル）－５－（１－（２－（ピリミジン－２－イル）ヒドラゾノ）エチル）チアゾール　化合物（化合物番号：Ｂ－００７） Example 9
-Synthesis of Compound of the Present Invention (Compound No .: B-007)-
4-Methyl-2- (pyridin-3-yl) -5- (1- (2- (pyrimidin-2-yl) hydrazono) ethyl) thiazole Compound (Compound No .: B-007)
Figure JPOXMLDOC01-appb-C000094
Figure JPOXMLDOC01-appb-C000094
　１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　（０．２０　ｇ，　０．７８　ｍｍｏｌ）のエタノール溶液（５ｍＬ）に２－ヒドラジニルピリミジン（０．３４　ｇ，　３．１　ｍｍｏｌ）、酢酸１滴を加え還流下にて２時間攪拌した。反応溶液に水を加え、析出した固体をろ過、乾燥することで目的物（０．１７　ｇ）を収率７２％で得た。
　１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　１０．３４　（１Ｈ，　ｓ），　９．１１　（１Ｈ，　ｄｄ，　Ｊ　＝　２．３，　０．６　Ｈｚ），　８．６６　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．５　Ｈｚ），　８．５２　（２Ｈ，　ｄ，　Ｊ　＝　４．６　Ｈｚ），　８．２９　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．０，　２．３，　１．５　Ｈｚ），　７．５３　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．０，　４．７，　０．６　Ｈｚ），　６．９０　（１Ｈ，　ｄｄ，　Ｊ　＝　４．６　Ｈｚ），　２．６９　（３Ｈ，　ｓ），　２．４２　（３Ｈ，　ｓ）． 1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone (0.20 g, 0.78 mmol) in ethanol (5 mL) was added 2-hydrazinylpyrimidine (0. 34 g, 3.1 mmol) and 1 drop of acetic acid were added and stirred for 2 hours under reflux. Water was added to the reaction solution, and the precipitated solid was filtered and dried to obtain the desired product (0.17 g) in a yield of 72%.
1 H-NMR (DMSO-D 6 ) δ: 10.34 (1H, s), 9.11 (1H, dd, J = 2.3, 0.6 Hz), 8.66 (1H, dd, J = 4.7, 1.5 Hz), 8.52 (2H, d, J = 4.6 Hz), 8.29 (1H, ddd, J = 8.0, 2.3, 1.5 Hz) 7.53 (1H, ddd, J = 8.0, 4.7, 0.6 Hz), 6.90 (1H, dd, J = 4.6 Hz), 2.69 (3H, s), 2.42 (3H, s).
（実施例１０）
－本発明化合物（化合物番号：Ａ－０４８）の合成－
　３－（４－メチル－５－（１－（ピリミジン－２－イルオキシイミノ）エチル）チアゾール－２－イル）ピリジン　１－オキシド　化合物（化合物番号：Ａ－０４８） (Example 10)
-Synthesis of the compound of the present invention (Compound No .: A-048)-
3- (4-Methyl-5- (1- (pyrimidin-2-yloxyimino) ethyl) thiazol-2-yl) pyridine 1-oxide compound (Compound No .: A-048)
Figure JPOXMLDOC01-appb-C000095
Figure JPOXMLDOC01-appb-C000095
　１－（４－メチル－２－（ピリジン－３－イル）チアゾール－５－イル）エタノン　Ｏ－ピリミジン－２－イル　オキシム（０．８０　ｇ，　２．６　ｍｍｏｌ）のジクロロメタン溶液（１５　ｍＬ）にメタクロロ過安息香酸７０％品（０．８４　ｇ，　３．８　ｍｍｏｌ）を加え室温にて１５時間攪拌した。反応溶液に１０％チオ硫酸ナトリウム水溶液を加え、ジクロロメタンにて抽出を行い、飽和食塩水で洗浄した。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、シリカゲルクロマトグラフィー（酢酸エチル／メタノール＝４）にて精製を行い、目的化合物（０．６１　ｇ）を収率７３％で得た。
　１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　８．８１　（１Ｈ，　ｍ），　８．６７　（２Ｈ，　ｄ，　Ｊ　＝　４．７　Ｈｚ），　８．２４－８．２２　（１Ｈ，　ｍ），　７．７７－７．７５　（１Ｈ，　ｍ），　７．３６－７．３４　（１Ｈ，　ｍ），　７．１３　（１Ｈ，　ｔ，　Ｊ　＝　４．７　Ｈｚ），　２．７４　（３Ｈ，　ｓ），　２．６１　（３Ｈ，　ｓ）． 1- (4-Methyl-2- (pyridin-3-yl) thiazol-5-yl) ethanone O-pyrimidin-2-yl oxime (0.80 g, 2.6 mmol) in dichloromethane solution (15 mL) A 70% product of metachloroperbenzoic acid (0.84 g, 3.8 mmol) was added, and the mixture was stirred at room temperature for 15 hours. A 10% aqueous sodium thiosulfate solution was added to the reaction solution, extracted with dichloromethane, and washed with saturated brine. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate / methanol = 4) to obtain the target compound (0.61 g) in a yield of 73%.
1 H-NMR (CDCl 3 ) δ: 8.81 (1H, m), 8.67 (2H, d, J = 4.7 Hz), 8.24-8.22 (1H, m), 7. 77-7.75 (1H, m), 7.36-7.34 (1H, m), 7.13 (1H, t, J = 4.7 Hz), 2.74 (3H, s), 2 .61 (3H, s).
（実施例１１）
－本発明化合物（化合物番号：Ｃ－００９）の合成－
段階１：エチル　１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－カルボキシレート (Example 11)
-Synthesis of the compound of the present invention (Compound No .: C-009)-
Step 1: Ethyl 1- (pyridin-3-yl) -1H-pyrazole-4-carboxylate
Figure JPOXMLDOC01-appb-C000096
 
Figure JPOXMLDOC01-appb-C000096
 
　３―ヨードピリジン　（１．９０ｇ，　９．２８ｍｍｏｌ）のＮ，Ｎ－ジメチルホルムアミド溶液（１０　ｍＬ）にエチル　４－ピラゾールカルボキシレート（１．００　ｇ、７．１４　ｍｍｏｌ）、（Ｓ，Ｓ）－（＋）－Ｎ，Ｎ’－ジメチル－１，２－シクロヘキサンジアミン（２．０３　ｇ、１４．３　ｍｍｏｌ）およびヨウ化銅（Ｉ）（０．６８　ｇ、３．６　ｍｍｏｌ）を加え、１１０℃にて６時間攪拌した。反応溶液に水を加え、酢酸エチルにて抽出を行い、飽和塩化アンモニウム水溶液で洗浄した。得られた有機層をセライトろ過し、硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、シリカゲルクロマトグラフィー（ヘキサン／酢酸エチル＝１）にて精製を行い、目的化合物（１．３２　ｇ）を収率８５％で得た。
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　９．０２　（１Ｈ，　ｓ），　８．６３　（１Ｈ，　ｄ，　Ｊ　＝　４．４　Ｈｚ），　８．４７　（１Ｈ，　ｓ），　８．１５　（１Ｈ，　ｓ），　８．１０－８．０７　（１Ｈ，　ｍ），　７．４７－７．４５　（１Ｈ，　ｍ），　４．３９－４．３１　（２Ｈ，　ｍ），　１．４１－１．３４　（３Ｈ，　ｍ）． To a solution of 3-iodopyridine (1.90 g, 9.28 mmol) in N, N-dimethylformamide (10 mL), ethyl 4-pyrazolecarboxylate (1.00 g, 7.14 mmol), (S, S)- (+)-N, N′-dimethyl-1,2-cyclohexanediamine (2.03 g, 14.3 mmol) and copper (I) iodide (0.68 g, 3.6 mmol) were added, and 110 Stir at 6 ° C. for 6 hours. Water was added to the reaction solution, extracted with ethyl acetate, and washed with a saturated aqueous ammonium chloride solution. The obtained organic layer was filtered through Celite and dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (hexane / ethyl acetate = 1) to obtain the target compound (1.32 g) in a yield of 85%.
1 H-NMR (CDCl 3 ) δ: 9.02 (1H, s), 8.63 (1H, d, J = 4.4 Hz), 8.47 (1H, s), 8.15 (1H, s), 8.10-8.07 (1H, m), 7.47-7.45 (1H, m), 4.39-4.31 (2H, m), 1.41-1.34 ( 3H, m).
段階２：１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－カルボン酸 Step 2: 1- (Pyridin-3-yl) -1H-pyrazole-4-carboxylic acid
Figure JPOXMLDOC01-appb-C000097
 
Figure JPOXMLDOC01-appb-C000097
 
　エチル　１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－カルボキシレート（５．００　ｇ，２３．０　ｍｍｏｌ）のメタノール溶液（２００　ｍＬ）に水酸化リチウム１水和物（５．７９　ｇ、１３８　ｍｍｏｌ）の水溶液（２０　ｍＬ）を加え、室温にて５時間攪拌した。メタノールを減圧留去し、濃塩酸にてｐＨを７に調整した後、水を５　ｍＬ減圧留去し、フィルターろ過により目的化合物（３．０８　ｇ）を収率７１％で得た。
１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　９．１７　（１Ｈ，　ｄ，　Ｊ　＝　２．８　Ｈｚ），　９．０６　（１Ｈ，　ｓ），　８．５８　（１Ｈ，　ｄｄ，　Ｊ　＝　４．６，　１．２　Ｈｚ），　８．３３－８．３１　（１Ｈ，　ｍ），　８．１１　（１Ｈ，　ｓ），　７．５８　（１Ｈ，　ｄｄ，　Ｊ　＝　８．４，　４．７　Ｈｚ）． Lithium hydroxide monohydrate (5.79 g) was added to a methanol solution (200 mL) of ethyl 1- (pyridin-3-yl) -1H-pyrazole-4-carboxylate (5.00 g, 23.0 mmol). 138 mmol) in water (20 mL) was added and stirred at room temperature for 5 hours. Methanol was distilled off under reduced pressure, pH was adjusted to 7 with concentrated hydrochloric acid, 5 mL of water was distilled off under reduced pressure, and the target compound (3.08 g) was obtained in a yield of 71% by filter filtration.
1 H-NMR (DMSO-D 6 ) δ: 9.17 (1H, d, J = 2.8 Hz), 9.06 (1H, s), 8.58 (1H, dd, J = 4.6) , 1.2 Hz), 8.33-8.31 (1H, m), 8.11 (1H, s), 7.58 (1H, dd, J = 8.4, 4.7 Hz).
段階３：Ｎ－メトキシ－Ｎ－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－カルボキシアミド Step 3: N-methoxy-N-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carboxamide
Figure JPOXMLDOC01-appb-C000098
Figure JPOXMLDOC01-appb-C000098
　１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－カルボン酸（３．００　ｇ，１５．９　ｍｍｏｌ）のトルエン溶液（４０　ｍＬ）にＮ，Ｎ－ジメチルホルムアミド６滴および塩化チオニル（３．７７　ｇ、３１．７　ｍｍｏｌ）を加え、７５℃にて２時間攪拌した。溶媒を減圧留去し、ジクロロメタン（４０　ｍＬ）を加えた。その後、トリエチルアミン（４．８１　ｇ、４７．６　ｍｍｏｌ）、Ｎ，Ｏ－ジメチルヒドロキシアミン塩酸塩（２．３２　ｇ、２３．８　ｍｍｏｌ）および４－ジメチルアミノピリジン（０．０１９　ｇ、０．１６　ｍｍｏｌ）を加え、室温下にて３時間攪拌した。反応溶液に水を加え、ジクロロメタンにて抽出を行い、飽和食塩水で洗浄した。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、得られた固体をジイソプロピルエーテル／ヘキサンで洗浄し、目的物（２．６０　ｇ）を収率６８％で得た。
１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　９．１９　（１Ｈ，　ｄ，　Ｊ　＝　２．４　Ｈｚ），　９．０１　（１Ｈ，　ｓ），　８．６０　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．４　Ｈｚ），　８．３５－８．３４　（１Ｈ，　ｍ），　８．１９　（１Ｈ，　ｓ），　７．５９　（１Ｈ，　ｄｄ，　Ｊ　＝　８．３，　４．６　Ｈｚ），　３．７８　（３Ｈ，　ｓ），　３．２８　（３Ｈ，　ｓ）． To a toluene solution (40 mL) of 1- (pyridin-3-yl) -1H-pyrazole-4-carboxylic acid (3.00 g, 15.9 mmol), 6 drops of N, N-dimethylformamide and thionyl chloride (3 .77 g, 31.7 mmol) was added, and the mixture was stirred at 75 ° C. for 2 hours. The solvent was removed in vacuo and dichloromethane (40 mL) was added. Then triethylamine (4.81 g, 47.6 mmol), N, O-dimethylhydroxyamine hydrochloride (2.32 g, 23.8 mmol) and 4-dimethylaminopyridine (0.019 g, 0.16). mmol) and stirred at room temperature for 3 hours. Water was added to the reaction solution, extracted with dichloromethane, and washed with saturated brine. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the resulting solid was washed with diisopropyl ether / hexane to obtain the desired product (2.60 g) in a yield of 68%.
1 H-NMR (DMSO-D 6 ) δ: 9.19 (1H, d, J = 2.4 Hz), 9.01 (1H, s), 8.60 (1H, dd, J = 4.7) , 1.4 Hz), 8.35-8.34 (1H, m), 8.19 (1H, s), 7.59 (1H, dd, J = 8.3, 4.6 Hz), 3 .78 (3H, s), 3.28 (3H, s).
段階４：１－（１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル）エタノン　 Step 4: 1- (1- (Pyridin-3-yl) -1H-pyrazol-4-yl) ethanone
Figure JPOXMLDOC01-appb-C000099
Figure JPOXMLDOC01-appb-C000099
　Ｎ－メトキシ－Ｎ－メチル－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－カルボキシアミド（２．６０　ｇ，　１１．２　ｍｍｏｌ）のテトラヒドロフラン溶液（５０　ｍＬ）を０℃に冷却し、１．４　ｍｏｌ／Ｌメチルマグネシウムブロミドのテトラヒドロフラン溶液（８．８　ｍＬ，　１２．３　ｍｍｏｌ）を加えた。０℃で２時間攪拌した。反応溶液に飽和塩化アンモニウム水溶液を加え、酢酸エチルにて抽出を行い、飽和食塩水で洗浄した。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し得られた固体をジイソプロピルエーテルで洗浄し、目的物（１．０２　ｇ）を収率４９％で得た。
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　９．０３　（１Ｈ，　ｄ，　Ｊ　＝　２．８　Ｈｚ），　８．６４　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．４　Ｈｚ），　８．４５　（１Ｈ，　ｓ），　８．１５　（１Ｈ，　ｓ），　８．０９－８．０７　（１Ｈ，　ｍ），　７．４７　（１Ｈ，　ｄｄ，　Ｊ　＝　８．３，　４．９　Ｈｚ），　２．５３　（３Ｈ，　ｓ）． A tetrahydrofuran solution (50 mL) of N-methoxy-N-methyl-1- (pyridin-3-yl) -1H-pyrazole-4-carboxamide (2.60 g, 11.2 mmol) was cooled to 0 ° C. 1.4 mol / L methylmagnesium bromide in tetrahydrofuran (8.8 mL, 12.3 mmol) was added. Stir at 0 ° C. for 2 hours. A saturated aqueous ammonium chloride solution was added to the reaction solution, extracted with ethyl acetate, and washed with saturated brine. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the resulting solid was washed with diisopropyl ether to obtain the desired product (1.02 g) in a yield of 49%.
1 H-NMR (CDCl 3 ) δ: 9.03 (1H, d, J = 2.8 Hz), 8.64 (1H, dd, J = 4.7, 1.4 Hz), 8.45 ( 1H, s), 8.15 (1H, s), 8.09-8.07 (1H, m), 7.47 (1H, dd, J = 8.3, 4.9 Hz), 2.53 (3H, s).
段階５：　１－（１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル）エタノン　オキシム Step 5: 1- (1- (Pyridin-3-yl) -1H-pyrazol-4-yl) ethanone oxime
Figure JPOXMLDOC01-appb-C000100
Figure JPOXMLDOC01-appb-C000100
　１－（１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル）エタノン（０．２５　ｇ，　１．３　ｍｍｏｌ）のエタノール溶液（５　ｍＬ）にヒドロキシルアミン５０％水溶液（０．４４　ｇ，　６．７　ｍｍｏｌ）を加え、還流下にて５時間攪拌した。反応溶液に水（２ｍＬ）を加え、室温まで冷却した後、析出した固体をろ過、ジイソプロピルエーテルで洗浄し、目的化合物（０．１５　ｇ）を収率４０％で得た。
ｍａｊｏｒ：１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　１０．９４　（１Ｈ，　ｓ），　９．１４　（１Ｈ，　ｄ，　Ｊ　＝　２．４　Ｈｚ），　８．８６　（１Ｈ，　ｓ），　８．５４　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．４　Ｈｚ），　８．２７－８．２６　（１Ｈ，　ｍ），　８．０２　（１Ｈ，　ｓ），　７．５９－７．５５　（１Ｈ，　ｍ），　２．１４　（３Ｈ，　ｓ）．
ｍｉｎｏｒ：１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　１１．０９　（１Ｈ，　ｓ），　９．１５　（１Ｈ，　ｄ，　Ｊ　＝　２．１　Ｈｚ），　９．０４　（１Ｈ，　ｓ），　８．５６　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．４　Ｈｚ），　８．３２　（１Ｈ，　ｓ），　８．３１－８．２９　（１Ｈ，　ｍ），　７．５７－７．５６　（１Ｈ，　ｍ），　２．１７　（３Ｈ，　ｓ）． 1- (1- (Pyridin-3-yl) -1H-pyrazol-4-yl) ethanone (0.25 g, 1.3 mmol) in an ethanol solution (5 mL) was added a hydroxylamine 50% aqueous solution (0.44). g, 6.7 mmol) was added and stirred under reflux for 5 hours. After adding water (2 mL) to the reaction solution and cooling to room temperature, the precipitated solid was filtered and washed with diisopropyl ether to obtain the target compound (0.15 g) in a yield of 40%.
major: 1 H-NMR (DMSO-D 6 ) δ: 10.94 (1H, s), 9.14 (1H, d, J = 2.4 Hz), 8.86 (1H, s), 8. 54 (1H, dd, J = 4.7, 1.4 Hz), 8.27-8.26 (1H, m), 8.02 (1H, s), 7.59-7.55 (1H, m), 2.14 (3H, s).
minor: 1 H-NMR (DMSO-D 6 ) δ: 11.09 (1H, s), 9.15 (1H, d, J = 2.1 Hz), 9.04 (1H, s), 8. 56 (1H, dd, J = 4.7, 1.4 Hz), 8.32 (1H, s), 8.31-8.29 (1H, m), 7.57-7.56 (1H, m), 2.17 (3H, s).
段階６：　１－（１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル）エタノン　Ｏ－ピリミジン－２－イル　オキシム（化合物番号：Ｃ－００９） Step 6: 1- (1- (Pyridin-3-yl) -1H-pyrazol-4-yl) ethanone O-pyrimidin-2-yl oxime (compound number: C-009)
Figure JPOXMLDOC01-appb-C000101
Figure JPOXMLDOC01-appb-C000101
１－（１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル）エタノン　オキシム　（０．１５　ｇ，　０．７１　ｍｍｏｌ）のＮ，Ｎ－ジメチルホルムアミド溶液（３　ｍＬ）に炭酸カリウム（０．４２　ｇ，３．０　ｍｍｏｌ）および２－ブロモピリミジン（０．７０　ｇ，４．５　ｍｍｏｌ）を加え、１２０℃にて６時間攪拌した。反応溶液に水を加え、酢酸エチルにて抽出を行った。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し、得られた固体をシリカゲルクロマトグラフィー（酢酸エチル／メタノール＝９）にて精製を行い、目的化合物（０．６７　ｇ）を収率３２％で得た。
ｍａｊｏｒ：１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　９．０４　（１Ｈ，　ｄ，　Ｊ　＝　２．１　Ｈｚ），　８．６７　（２Ｈ，　ｄ，　Ｊ　＝　４．６　Ｈｚ），　８．６０　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．４　Ｈｚ），　８．４５　（１Ｈ，　ｓ），　８．１４　（１Ｈ，　ｓ），　８．１０－８．０８　（１Ｈ，　ｍ），　７．４６－７．４３　（１Ｈ，　ｍ），　７．１１－７．０９　（１Ｈ，　ｍ），　２．５４　（３Ｈ，　ｓ）．
ｍｉｎｏｒ：１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　９．１０　（１Ｈ，　ｄ，　Ｊ　＝　２．１　Ｈｚ），　８．９７　（１Ｈ，　ｓ），　８．６８　（２Ｈ，　ｄ，　Ｊ　＝　４．６　Ｈｚ），　８．６３　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．４　Ｈｚ），　８．２１　（１Ｈ，　ｓ），　８．１３－８．１２　（１Ｈ，　ｍ），　７．４８－７．４７　（１Ｈ，　ｍ），　７．１１－７．１１　（１Ｈ，　ｍ），　２．５３　（３Ｈ，　ｓ）． 1- (1- (Pyridin-3-yl) -1H-pyrazol-4-yl) ethanone oxime (0.15 g, 0.71 mmol) in N, N-dimethylformamide (3 mL) was added potassium carbonate (3 mL). 0.42 g, 3.0 mmol) and 2-bromopyrimidine (0.70 g, 4.5 mmol) were added, and the mixture was stirred at 120 ° C. for 6 hours. Water was added to the reaction solution, and extraction was performed with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the obtained solid was purified by silica gel chromatography (ethyl acetate / methanol = 9) to obtain the target compound (0.67 g) in a yield of 32%.
major: 1 H-NMR (CDCl 3 ) δ: 9.04 (1H, d, J = 2.1 Hz), 8.67 (2H, d, J = 4.6 Hz), 8.60 (1H, dd, J = 4.7, 1.4 Hz), 8.45 (1H, s), 8.14 (1H, s), 8.10-8.08 (1H, m), 7.46-7 .43 (1H, m), 7.11-7.09 (1H, m), 2.54 (3H, s).
minor: 1 H-NMR (CDCl 3 ) δ: 9.10 (1H, d, J = 2.1 Hz), 8.97 (1H, s), 8.68 (2H, d, J = 4.6) Hz), 8.63 (1H, dd, J = 4.7, 1.4 Hz), 8.21 (1H, s), 8.13-8.12 (1H, m), 7.48-7 .47 (1H, m), 7.11-7.11 (1H, m), 2.53 (3H, s).
（実施例１２）－本発明化合物（化合物番号：Ｄ－００４）の合成－
メチル　２－（１－（１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル）エチリデン）ヒドラジンカルボキシレート Example 12 Synthesis of Compound of the Present Invention (Compound No. D-004)
Methyl 2- (1- (1- (1- (pyridin-3-yl) -1H-pyrazol-4-yl) ethylidene) hydrazinecarboxylate
Figure JPOXMLDOC01-appb-C000102
 
　１－（１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル）エタノン（０．１０　ｇ，　０．５３　ｍｍｏｌ）のエタノール溶液（３　ｍＬ）にカルバジン酸メチル（０．１９　ｇ，　２．１　ｍｍｏｌ）および酢酸を３滴加えた後、還流下にて３時間攪拌した。反応溶液に水（２ｍＬ）を加え、室温まで冷却した後、析出した固体をろ過、ジイソプロピルエーテルで洗浄し、目的化合物（０．０８６　ｇ）を収率６２％で得た。
１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　１０．０５　（１Ｈ，　ｂｒ　ｓ），　９．１４　（１Ｈ，　ｄ，　Ｊ　＝　２．４　Ｈｚ），　８．９１　（１Ｈ，　ｓ），　８．５４　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．４　Ｈｚ），　８．２８－８．２７　（１Ｈ，　ｍ），　８．０６　（１Ｈ，　ｓ），　７．５７　（１Ｈ，　ｄｄ，　Ｊ　＝　８．３，　４．６　Ｈｚ），　３．７０　（３Ｈ，　ｓ），　２．２０　（３Ｈ，　ｓ）．
Figure JPOXMLDOC01-appb-C000102

1- (1- (Pyridin-3-yl) -1H-pyrazol-4-yl) ethanone (0.10 g, 0.53 mmol) in ethanol solution (3 mL) was added methyl carbadate (0.19 g, 2.1 mmol) and 3 drops of acetic acid were added, followed by stirring under reflux for 3 hours. After adding water (2 mL) to the reaction solution and cooling to room temperature, the precipitated solid was filtered and washed with diisopropyl ether to obtain the target compound (0.086 g) in a yield of 62%.
1 H-NMR (DMSO-D 6 ) δ: 10.05 (1H, br s), 9.14 (1H, d, J = 2.4 Hz), 8.91 (1H, s), 8.54 (1H, dd, J = 4.7, 1.4 Hz), 8.28-8.27 (1H, m), 8.06 (1H, s), 7.57 (1H, dd, J = 8 .3, 4.6 Hz), 3.70 (3H, s), 2.20 (3H, s).
（実施例１３）
－本発明化合物（化合物番号：Ｄ－００６）の合成－
段階１：　２－（２－（１－（１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル）エチリデン）ヒドラジニル）ピリミジン (Example 13)
-Synthesis of the compound of the present invention (Compound No .: D-006)-
Step 1: 2- (2- (1- (1- (Pyridin-3-yl) -1H-pyrazol-4-yl) ethylidene) hydrazinyl) pyrimidine
Figure JPOXMLDOC01-appb-C000103
Figure JPOXMLDOC01-appb-C000103
　１－（１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル）エタノン（０．１５　ｇ，　０．８０　ｍｍｏｌ）のエタノール溶液（３　ｍＬ）に２－ヒドラジニルピリミジン（０．１７　ｇ，　１．６　ｍｍｏｌ）および酢酸を３滴加えた後、還流下にて６時間攪拌した。反応溶液に水（２ｍＬ）を加え、室温まで冷却した後、析出した固体をろ過、ジイソプロピルエーテルで洗浄し、目的化合物（０．２０　ｇ）を収率８９％で得た。
１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　１０．０１　（１Ｈ，　ｂｒ　ｓ），　９．１６　（１Ｈ，　ｄ，　Ｊ　＝　２．４　Ｈｚ），　８．９３　（１Ｈ，　ｓ），　８．５４　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．４　Ｈｚ），　８．４８　（２Ｈ，　ｄ，　Ｊ　＝　４．６　Ｈｚ），　８．３１－８．２７　（１Ｈ，　ｍ），　８．１３　（１Ｈ，　ｓ），　７．６０－７．５４　（１Ｈ，　ｍ），　６．８５　（１Ｈ，　ｔ，　Ｊ　＝　４．６　Ｈｚ），　２．３２　（３Ｈ，　ｓ）． 1- (1- (Pyridin-3-yl) -1H-pyrazol-4-yl) ethanone (0.15 g, 0.80 mmol) in ethanol (3 mL) was added 2-hydrazinylpyrimidine (0. 17 g, 1.6 mmol) and 3 drops of acetic acid were added, followed by stirring under reflux for 6 hours. Water (2 mL) was added to the reaction solution, and after cooling to room temperature, the precipitated solid was filtered and washed with diisopropyl ether to obtain the target compound (0.20 g) in a yield of 89%.
1 H-NMR (DMSO-D 6 ) δ: 10.01 (1H, br s), 9.16 (1H, d, J = 2.4 Hz), 8.93 (1H, s), 8.54 (1H, dd, J = 4.7, 1.4 Hz), 8.48 (2H, d, J = 4.6 Hz), 8.31-8.27 (1H, m), 8.13 ( 1H, s), 7.60-7.54 (1H, m), 6.85 (1H, t, J = 4.6 Hz), 2.32 (3H, s).
（実施例１４）
－本発明化合物（化合物番号：Ｄ－００１）の合成－
段階１：メチル　２－（１－（５－（ピリジン－３－イル）－１，３，４－チアジアゾール－２－イル）エチリデン）ヒドラジンカルボキシレート (Example 14)
-Synthesis of the compound of the present invention (Compound No .: D-001)-
Step 1: Methyl 2- (1- (5- (pyridin-3-yl) -1,3,4-thiadiazol-2-yl) ethylidene) hydrazine carboxylate
Figure JPOXMLDOC01-appb-C000104
Figure JPOXMLDOC01-appb-C000104
　１－（５－（ピリジン－３－イル）－１，３，４－チアジアゾール－２－イル）エタノン（０．１５　ｇ，　０．７３　ｍｍｏｌ）のエタノール溶液（３　ｍＬ）にカルバジン酸メチル（０．１７　ｇ，　１．６　ｍｍｏｌ）および酢酸を３滴加えた後、還流下にて３時間攪拌した。反応溶液に水（２ｍＬ）を加え、室温まで冷却した後、析出した固体をろ過、ジイソプロピルエーテルで洗浄し、目的化合物（０．０９５　ｇ）を収率４７％で得た。
１０：１　ｍｉｘｔｕｒｅ
ｍａｊｏｒ：１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　１０．９０　（１Ｈ，　ｂｒ　ｓ），　９．２０－９．２０　（１Ｈ，　ｍ），　８．７６　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．７　Ｈｚ），　８．４２　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．０，　２．２，　１．６　Ｈｚ），　７．６１　（１Ｈ，　ｄｄｄ，　Ｊ　＝　８．０，　４．９，　０．９　Ｈｚ），　３．７６　（３Ｈ，　ｓ），　２．４３　（３Ｈ，　ｓ）．
ｍｉｎｏｒ：１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　１２．３５　（１Ｈ，　ｂｒ　ｓ），　９．２５　（１Ｈ，　ｄ，　Ｊ　＝　１．８　Ｈｚ），　８．８１－８．８０　（１Ｈ，　ｍ），　８．４９－８．４６　（１Ｈ，　ｍ），　７．６７－７．６４　（１Ｈ，　ｍ），　３．７８　（３Ｈ，　ｓ），　２．４３　（３Ｈ，　ｓ）． To a solution of 1- (5- (pyridin-3-yl) -1,3,4-thiadiazol-2-yl) ethanone (0.15 g, 0.73 mmol) in ethanol (3 mL) was added methyl carbamate (0 .17 g, 1.6 mmol) and 3 drops of acetic acid were added, followed by stirring under reflux for 3 hours. After adding water (2 mL) to the reaction solution and cooling to room temperature, the precipitated solid was filtered and washed with diisopropyl ether to obtain the target compound (0.095 g) in a yield of 47%.
10: 1 mixture
major: 1 H-NMR (DMSO-D 6 ) δ: 10.90 (1H, br s), 9.20-9.20 (1H, m), 8.76 (1H, dd, J = 4.7) , 1.7 Hz), 8.42 (1H, ddd, J = 8.0, 2.2, 1.6 Hz), 7.61 (1H, ddd, J = 8.0, 4.9, 0 .9 Hz), 3.76 (3H, s), 2.43 (3H, s).
minor: 1 H-NMR (DMSO-D 6 ) δ: 12.35 (1H, br s), 9.25 (1H, d, J = 1.8 Hz), 8.81-8.80 (1H, m), 8.49-8.46 (1H, m), 7.67-7.64 (1H, m), 3.78 (3H, s), 2.43 (3H, s).
（実施例１５）
－本発明化合物（化合物番号：Ｄ－００６）の合成－
段階１：２－（ピリジン－３－イル）－５－（１－（２－（ピリミジン－２－イル）ヒドラゾン）エチル）－１，３，４－チアジアゾール (Example 15)
-Synthesis of the compound of the present invention (Compound No .: D-006)-
Step 1: 2- (Pyridin-3-yl) -5- (1- (2- (pyrimidin-2-yl) hydrazone) ethyl) -1,3,4-thiadiazole
Figure JPOXMLDOC01-appb-C000105
 
Figure JPOXMLDOC01-appb-C000105
 
　１－（５－（ピリジン－３－イル）－１，３，４－チアジアゾール－２－イル）エタノン（０．１５　ｇ，　０．７３　ｍｍｏｌ）のエタノール溶液（３　ｍＬ）に２－ヒドラジニルピリミジン（０．１６　ｇ，　１．５　ｍｍｏｌ）および酢酸を３滴加えた後、還流下にて６時間攪拌した。反応溶液に水（２ｍＬ）を加え、室温まで冷却した後、析出した固体をろ過、ジイソプロピルエーテルで洗浄し、目的化合物（０．０９５　ｇ）を収率４３％で得た。
１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　１０．９５　（１Ｈ，　ｂｒ　ｓ），　９．２１　（１Ｈ，　ｄｄ，　Ｊ　＝　２．３，　０．８　Ｈｚ），　８．７６　（１Ｈ，　ｄｄ，　Ｊ　＝　４．９，　１．５　Ｈｚ），　８．６０　（２Ｈ，　ｄ，　Ｊ　＝　４．９　Ｈｚ），　８．４４－８．４３　（１Ｈ，　ｍ），　７．６２－７．６０　（１Ｈ，　ｍ），　７．０２　（１Ｈ，　ｔ，　Ｊ　＝　４．７　Ｈｚ），　２．５４　（３Ｈ，　ｓ）． 2-Hydrazinyl in ethanol solution (3 mL) of 1- (5- (pyridin-3-yl) -1,3,4-thiadiazol-2-yl) ethanone (0.15 g, 0.73 mmol) After adding 3 drops of pyrimidine (0.16 g, 1.5 mmol) and acetic acid, the mixture was stirred for 6 hours under reflux. After adding water (2 mL) to the reaction solution and cooling to room temperature, the precipitated solid was filtered and washed with diisopropyl ether to obtain the target compound (0.095 g) in a yield of 43%.
1 H-NMR (DMSO-D 6 ) δ: 10.95 (1H, br s), 9.21 (1H, dd, J = 2.3, 0.8 Hz), 8.76 (1H, dd, J = 4.9, 1.5 Hz), 8.60 (2H, d, J = 4.9 Hz), 8.44-8.43 (1H, m), 7.62-7.60 (1H M), 7.02 (1H, t, J = 4.7 Hz), 2.54 (3H, s).
（実施例１６）
－本発明化合物（化合物番号：Ｄ－００９）の合成－
段階１：５－（１－（２－（ピリミジン－２－イル）ヒドラゾン）エチル）－２，３’－ビピリジン (Example 16)
-Synthesis of the present compound (Compound No .: D-009)-
Step 1: 5- (1- (2- (pyrimidin-2-yl) hydrazone) ethyl) -2,3′-bipyridine
Figure JPOXMLDOC01-appb-C000106
Figure JPOXMLDOC01-appb-C000106
　１－（［２，３’－ビピリジン］－５－イル）エタノン（０．１５　ｇ，　０．７６　ｍｍｏｌ）のエタノール溶液（３　ｍＬ）に２－ヒドラジニルピリミジン（０．１７　ｇ，　１．５　ｍｍｏｌ）および酢酸を３滴加えた後、還流下にて６時間攪拌した。反応溶液に炭酸水素ナトリウム水溶液を加え、酢酸エチルにて抽出を行い、飽和食塩水で洗浄した。得られた有機層を硫酸マグネシウムで乾燥した後、硫酸マグネシウムをフィルターにて取り除いた。溶媒を減圧留去し得られた固体をジイソプロピルエーテルで洗浄し、目的物（０．１３ｇ）を収率５９％で得た。
１Ｈ－ＮＭＲ　（ＤＭＳＯ－Ｄ６）　δ：　１０．３８　（１Ｈ，　ｂｒ　ｓ），　９．３１　（１Ｈ，　ｄ，　Ｊ　＝　１．５　Ｈｚ），　９．１１　（１Ｈ，　ｄ，　Ｊ　＝　１．５　Ｈｚ），　８．６５　（１Ｈ，　ｄｄ，　Ｊ　＝　４．７，　１．７　Ｈｚ），　８．５４　（２Ｈ，　ｄ，　Ｊ　＝　４．９　Ｈｚ），　８．４９－８．４８　（１Ｈ，　ｍ），　８．３２　（１Ｈ，　ｄｄ，　Ｊ　＝　８．３，　２．４　Ｈｚ），　８．１２　（１Ｈ，　ｄｄ，　Ｊ　＝　８．６，　０．６　Ｈｚ），　７．５６－７．５４　（１Ｈ，　ｍ），　６．９３　（１Ｈ，　ｔ，　Ｊ　＝　４．７　Ｈｚ），　２．４０　（３Ｈ，　ｓ）． To a solution of 1-([2,3′-bipyridin] -5-yl) ethanone (0.15 g, 0.76 mmol) in ethanol (3 mL) was added 2-hydrazinylpyrimidine (0.17 g, 1. 5 mmol) and 3 drops of acetic acid were added, followed by stirring for 6 hours under reflux. An aqueous sodium hydrogen carbonate solution was added to the reaction solution, extracted with ethyl acetate, and washed with saturated brine. The obtained organic layer was dried over magnesium sulfate, and then magnesium sulfate was removed with a filter. The solvent was distilled off under reduced pressure, and the resulting solid was washed with diisopropyl ether to obtain the desired product (0.13 g) in a yield of 59%.
1 H-NMR (DMSO-D 6 ) δ: 10.38 (1H, br s), 9.31 (1H, d, J = 1.5 Hz), 9.11 (1H, d, J = 1. 5 Hz), 8.65 (1H, dd, J = 4.7, 1.7 Hz), 8.54 (2H, d, J = 4.9 Hz), 8.49-8.48 (1H, m), 8.32 (1H, dd, J = 8.3, 2.4 Hz), 8.12 (1H, dd, J = 8.6, 0.6 Hz), 7.56-7.54 (1H, m), 6.93 (1H, t, J = 4.7 Hz), 2.40 (3H, s).
　以下の第５表～第８表に、本実施例において合成した化合物を含む、本発明化合物の化合物番号とその詳細を示す。 Tables 5 to 8 below show the compound numbers and details of the compounds of the present invention, including the compounds synthesized in this example.
（第５表） (Table 5)
Figure JPOXMLDOC01-appb-C000107
Figure JPOXMLDOC01-appb-C000107
第５表（１）
Figure JPOXMLDOC01-appb-T000108
 Table 5 (1)
Figure JPOXMLDOC01-appb-T000108
第５表（２）
Figure JPOXMLDOC01-appb-T000109
 Table 5 (2)
Figure JPOXMLDOC01-appb-T000109
第５表（３）
Figure JPOXMLDOC01-appb-T000110
 Table 5 (3)
Figure JPOXMLDOC01-appb-T000110
第５表（４）
Figure JPOXMLDOC01-appb-T000111
 Table 5 (4)
Figure JPOXMLDOC01-appb-T000111
第５表（５）
Figure JPOXMLDOC01-appb-T000112
 Table 5 (5)
Figure JPOXMLDOC01-appb-T000112
第５表（６）
Figure JPOXMLDOC01-appb-T000113
 Table 5 (6)
Figure JPOXMLDOC01-appb-T000113
第５表（７）
Figure JPOXMLDOC01-appb-T000114
 Table 5 (7)
Figure JPOXMLDOC01-appb-T000114
第５表（８）
Figure JPOXMLDOC01-appb-T000115
 Table 5 (8)
Figure JPOXMLDOC01-appb-T000115
（第６表）
Figure JPOXMLDOC01-appb-C000116
 (Table 6)
Figure JPOXMLDOC01-appb-C000116
第６表（１）
Figure JPOXMLDOC01-appb-T000117
 Table 6 (1)
Figure JPOXMLDOC01-appb-T000117
第６表（２）
Figure JPOXMLDOC01-appb-T000118
  Table 6 (2)
Figure JPOXMLDOC01-appb-T000118
（第７表） (Table 7)
Figure JPOXMLDOC01-appb-C000119
 
Figure JPOXMLDOC01-appb-C000119
 
第７表（１）
Figure JPOXMLDOC01-appb-T000120
 
  Table 7 (1)
Figure JPOXMLDOC01-appb-T000120

第７表（２）
Figure JPOXMLDOC01-appb-T000121
  Table 7 (2)
Figure JPOXMLDOC01-appb-T000121
第８表
Figure JPOXMLDOC01-appb-C000122
 Table 8
Figure JPOXMLDOC01-appb-C000122
第８表（１）
Figure JPOXMLDOC01-appb-T000123
  Table 8 (1)
Figure JPOXMLDOC01-appb-T000123
第８表（２）
Figure JPOXMLDOC01-appb-T000124
  Table 8 (2)
Figure JPOXMLDOC01-appb-T000124
[製剤例]
　次に、本発明化合物を有効成分として含有する製剤例を示すが、本発明はこれに限定されるものではない。
　なお、製剤例中、部とあるのは重量部を示す。
（製剤例１）
　一般式（Ｉ）で表される本発明化合物２０部、補助剤として、ポリオキシエチレンスチリルフェニルエーテル１０部、キシレン７０部、以上を均一に混合して乳剤を得た。 [Formulation example]
Next, although the formulation example which contains this invention compound as an active ingredient is shown, this invention is not limited to this.
In the preparation examples, “parts” means “parts by weight”.
(Formulation example 1)
An emulsion was obtained by uniformly mixing 20 parts of the present compound represented by formula (I) and 10 parts of polyoxyethylene styryl phenyl ether and 70 parts of xylene as auxiliary agents.
（製剤例２）
　一般式（Ｉ）で表される本発明化合物１０部、ラウリル硫酸ナトリウム２部、ジアルキルスルフォサクシネート２部、β‐ナフタレンスルホン酸ホルマリン縮合物ナトリウム塩１部、珪藻土８５部以上を均一に攪拌混合して水和剤を得た。 (Formulation example 2)
Uniformly stir 10 parts of the compound of the present invention represented by the general formula (I), 2 parts of sodium lauryl sulfate, 2 parts of dialkylsulfosuccinate, 1 part of sodium salt of β-naphthalenesulfonic acid formalin condensate and 85 parts of diatomaceous earth. A wettable powder was obtained by mixing.
（製剤例３）
　一般式（Ｉ）で表される本発明化合物０．３部、ホワイトカーボン０．３部を均一に混合し、クレー９９．２部、ドリレスＡ（三共アグロ製）０．２部を加えて、均一に粉砕混合し、粉剤を得た。 (Formulation example 3)
The compound of the present invention represented by the general formula (I) 0.3 part and white carbon 0.3 part are uniformly mixed, and 99.2 parts of clay and 0.2 part of Doriles A (Sankyo Agro) are added, Uniformly pulverized and mixed to obtain a powder.
（製剤例４）
　一般式（Ｉ）で表される本発明化合物３部、補助剤として、ポリオキシエチレン・ポリオキシプロピレン縮合物１．５部、カルボキシメチルセルロース３部、クレー６４．８部、タルク２７．７部、以上を均一に粉砕混合後、水を加えて混練し、造粒乾燥して粒剤を得た。 (Formulation example 4)
3 parts of the compound of the present invention represented by the general formula (I), 1.5 parts of polyoxyethylene / polyoxypropylene condensate, 3 parts of carboxymethylcellulose, 64.8 parts of clay, 27.7 parts of talc, After uniformly pulverizing and mixing the above, water was added and kneaded and granulated and dried to obtain granules.
（製剤例５）
　一般式（Ｉ）で表される本発明化合物１０部、β‐ナフタレンスルホン酸ホルマリン縮合物ナトリウム塩３部、トリスチリルフェノール１部、プロピレングリコール５部、シリコーン系消泡剤０．５部、水３３．５部を十分攪拌混合した後、キサンタンガム０．３部、水４６．７部を混合したものと再び攪拌混合してフロアブル剤を得た。 (Formulation example 5)
10 parts of the present compound represented by the general formula (I), 3 parts of β-naphthalenesulfonic acid formalin condensate sodium salt, 1 part of tristyrylphenol, 5 parts of propylene glycol, 0.5 part of silicone-based antifoaming agent, water 33.5 parts was sufficiently stirred and mixed, and then stirred and mixed again with a mixture of 0.3 part of xanthan gum and 46.7 parts of water to obtain a flowable agent.
（製剤例６）
　一般式（Ｉ）で表される本発明化合物２０部、ナフタレンスルホン酸ホルムアルデヒド縮合物金属塩６部、ジアルキルスルホコハク酸金属塩１部、炭酸カルシウム７３部、以上を均一に粉砕混合後、水を加えて混練し、造粒乾燥して顆粒水和剤を得た。 (Formulation Example 6)
20 parts of the compound of the present invention represented by the general formula (I), 6 parts of a metal salt of formaldehyde condensate of naphthalenesulfonic acid, 1 part of a metal salt of dialkylsulfosuccinic acid, 73 parts of calcium carbonate are uniformly ground and mixed, and then water is added. The mixture was kneaded and granulated and dried to obtain a granular wettable powder.
　上記で得られた製剤の使用に際しては、上記製剤を水で１～１００００倍に希釈して、又は希釈せずに直接散布する。 When using the preparation obtained above, the preparation is diluted 1 to 10,000 times with water or sprayed directly without dilution.
[試験例]
　次に、本発明化合物の有害生物防除剤としての有用性について、以下の試験例において具体的に説明するが、本発明はこれらのみに限定されるものではない。 [Test example]
Next, the usefulness of the compound of the present invention as a pest control agent will be specifically described in the following test examples, but the present invention is not limited to these.
（試験例１）
－ヒメトビウンカ（Ｌａｏｄｅｌｐｈａｘ　ｓｔｒｉａｔｅｌｌｕｓ）に対する殺虫試験－
　試験化合物（本発明化合物）を１００ｐｐｍに調製した２％アセトン水溶液１２．５ｍｌを、三角フラスコに入れてイネ幼苗の根部を浸漬する。さらに試験化合物を１０００ｐｐｍに調製したアセトン溶液２．５ｍｌをイネ幼苗の葉部に散布し風乾後、フラスコに透明プラスチックの筒を載せ、筒の内部にヒメトビウンカ３齢又は４齢幼虫１０頭を入れ、スポンジ栓で蓋をした。２５℃恒温室にて静置し、６日後に生死虫数を調査した。連制なし。 (Test Example 1)
-Insecticidal test against Japanese brown planthopper (Laodelfax striatellus)-
12.5 ml of 2% acetone aqueous solution prepared with 100 ppm of the test compound (the compound of the present invention) is placed in an Erlenmeyer flask, and the roots of rice seedlings are immersed. Furthermore, 2.5 ml of an acetone solution prepared with a test compound of 1000 ppm was sprayed on the leaves of rice seedlings and air-dried. Then, a transparent plastic tube was placed on the flask, and 10 3rd- and 4th-year-old larvae were placed inside the tube. Covered with a sponge plug. It left still in a 25 degreeC thermostat, and the number of live and dead insects was investigated 6 days afterward. No regime.
　上記試験の結果、化合物番号Ａ－００３、Ａ－００５、Ａ－０１６、Ａ－０２１、Ａ－０３０、Ａ－０４９、Ａ－０５４、Ａ－０５５、Ａ－０５７、Ａ－０６４、Ａ－０６５、Ａ－０６６、Ａ－０６９、Ａ－０８１、Ｂ－００４、Ｃ－００１、Ｃ－００３、Ｃ－００７の化合物が７０％以上の死虫率を示した。 As a result of the above test, compound numbers A-003, A-005, A-016, A-021, A-030, A-049, A-054, A-055, A-057, A-064, A-065 , A-066, A-069, A-081, B-004, C-001, C-003, and C-007 showed a death rate of 70% or more.
（試験例２）
－モモアカアブラムシ（Ｍｙｚｕｓ　ｐｅｒｓｉｃａｅ）に対する殺虫試験（散布試験）－
　試験化合物を１０００ｐｐｍに調製した２０％アセトン水溶液２．５ｍｌをモモアカアブラムシ１齢幼虫が寄生したダイコン幼苗の葉部に散布した。風乾後、２５℃恒温室にて静置し、５日後に生死虫数を調査した。連制なし。 (Test Example 2)
-Insecticidal test (spraying test) against peach aphid (Myzu persicae)-
2.5 ml of 20% acetone aqueous solution prepared with 1000 ppm of the test compound was sprayed on the leaves of Japanese radish seedlings infested with the first instar larvae. After air drying, it was left still in a constant temperature room at 25 ° C., and the number of live and dead insects was examined after 5 days. No regime.
　上記試験の結果、化合物番号Ａ－００１、Ａ－００２、Ａ－００３、Ａ－００４、Ａ－００５、Ａ－００６、Ａ－００７、Ａ－００８、Ａ－００９、Ａ－０１０、Ａ－０１１、Ａ－０１２、Ａ－０１４、Ａ－０１６、Ａ－０１７、Ａ－０２０、Ａ－０２１、Ａ－０２２、Ａ－０２３、Ａ－０２４、Ａ－０２６、Ａ－０２７、Ａ－０２８、Ａ－０２９、Ａ－０３０、Ａ－０３１、Ａ－０３２、Ａ－０３３、Ａ－０３４、Ａ－０３５、Ａ－０３６、Ａ－０３７、Ａ－０３８、Ａ－０３９、Ａ－０４０、Ａ－０４１、Ａ－０４２、Ａ－０４３、Ａ－０４４、Ａ－０４８、Ａ－０４９、Ａ－０５１、Ａ－０５３、Ａ－０５４、Ａ－０５５、Ａ－０５６、Ａ－０５７、Ａ－０５８、Ａ－０５９、Ａ－０６０、Ａ－０６１、Ａ－０６２、Ａ－０６６、Ａ－０６７、Ａ－０６９、Ａ－０７５、Ａ－０７８、Ａ－０８１、Ｂ－００１、Ｂ－００２、Ｂ－００３、Ｂ－００４、Ｂ－００５、Ｂ－００６、Ｂ－００７、Ｂ－００８、Ｂ－００９、Ｂ－０１２、Ｃ－００１、Ｃ－００４、Ｃ－００５、Ｃ－００６、Ｃ－００９、Ｃ－０１０、Ｃ－０１１、Ｄ－００１、Ｄ－００２、Ｄ－００３、Ｄ－００４、Ｄ－００５、Ｄ－００６、Ｄ－００８、Ｄ－００９の化合物が７０％以上の死虫率を示した。
　また、比較試験の結果を第9表に表す。 As a result of the above test, compound numbers A-001, A-002, A-003, A-004, A-005, A-006, A-007, A-008, A-009, A-010, A-011 A-012, A-014, A-016, A-017, A-020, A-021, A-022, A-023, A-024, A-026, A-027, A-028, A -029, A-030, A-031, A-032, A-033, A-034, A-035, A-036, A-037, A-038, A-039, A-040, A-041 A-042, A-043, A-044, A-048, A-049, A-051, A-053, A-054, A-055, A-056, A-057, A-058, A -059, A-060, A-061, A-062, A-066, A- 67, A-069, A-075, A-078, A-081, B-001, B-002, B-003, B-004, B-005, B-006, B-007, B-008, B-009, B-012, C-001, C-004, C-005, C-006, C-009, C-010, C-011, D-001, D-002, D-003, D- The compounds of 004, D-005, D-006, D-008, and D-009 showed a death rate of 70% or more.
The results of the comparative test are shown in Table 9.
第９表
Figure JPOXMLDOC01-appb-T000125
  Table 9
Figure JPOXMLDOC01-appb-T000125
（試験例３）
－モモアカアブラムシ（Ｍｙｚｕｓ　ｐｅｒｓｉｃａｅ）に対する殺虫試験（浸透移行性試験）－
　試験化合物を１００ｐｐｍに調製した２％アセトン水溶液１５～２０ｍｌを管瓶に入れモモアカアブラムシ１齢幼虫が寄生したダイコン幼苗の根部を浸漬した。２５℃恒温室にて静置し、５日後に生死虫数を調査した。連制なし。 (Test Example 3)
-Insecticide test (Penetration transferability test) against peach aphid (Myzu persicae)-
15-20 ml of a 2% acetone aqueous solution prepared with 100 ppm of the test compound was placed in a tube bottle, and the roots of Japanese radish seedlings parasitized with the first instar larvae of the green peach were immersed. After leaving still in a constant temperature room at 25 ° C., the number of live and dead insects was examined after 5 days. No regime.
　上記試験の結果、化合物番号Ａ－００１、Ａ－００２、Ａ－００５、Ａ－００６、Ａ－００８、Ａ－０２１、Ａ－０２３、Ａ－０３０、Ａ－０３５、Ａ－０４８、Ａ－０４９、Ａ－０５３、Ａ－０５４、Ａ－０６２、Ａ－０６４、Ａ－０７４、Ａ－０７５、Ａ－０７６、Ｂ－００４、Ｂ－００６、Ｂ－００７、Ｂ－０１２、Ｃ－００５、Ｃ－００６、Ｃ－００９、Ｄ－００１、Ｄ－００２、Ｄ－００３、Ｄ－００４、Ｄ－００５、Ｄ－００６、Ｄ－００７の化合物が７０％以上の死虫率を示した。 As a result of the above test, compound numbers A-001, A-002, A-005, A-006, A-008, A-021, A-023, A-030, A-035, A-048, A-049 , A-053, A-054, A-062, A-064, A-074, A-075, A-076, B-004, B-006, B-007, B-012, C-005, C The compounds of -006, C-009, D-001, D-002, D-003, D-004, D-005, D-006, and D-007 showed a death rate of 70% or more.
（試験例４）
－抵抗性ワタアブラムシ（Ａｐｈｉｓ　ｇｏｓｓｙｐｉｉ）に対する殺虫試験－
　１％寒天液６０ｍｌを入れた直径４ｃｍ×高さ５．５ｃｍのガラス容器に、直径３．２ｃｍのキュウリリーフディスクをのせ、感受性又は抵抗性ワタアブラムシの無翅成虫を４頭接種した。１日後に成虫を除去し産まれた幼虫のみに、試験化合物を所定濃度に調製した薬液０．５ｍｌを散布した。風乾後、容器を逆さにして２５℃恒温室にて静置した。処理５日後に生死虫数を調査し死虫率を算出した（２連制）。結果を第１０表に示す。
　なお、比較化合物としては、イミダクロプリドを用いた。 (Test Example 4)
-Insecticide test against resistant cotton aphid (Aphis gossypi)-
A cucumber relief disk with a diameter of 3.2 cm was placed in a glass container having a diameter of 4 cm and a height of 5.5 cm containing 60 ml of 1% agar solution, and 4 susceptible or resistant cotton aphid adults were inoculated. One day later, 0.5 ml of a medicinal solution prepared with a predetermined concentration of the test compound was sprayed only on the larvae born after removing the adults. After air drying, the container was inverted and allowed to stand in a constant temperature room at 25 ° C. Five days after the treatment, the number of live and dead insects was examined, and the death rate was calculated (two consecutive systems). The results are shown in Table 10.
In addition, imidacloprid was used as a comparative compound.
第１０表
Figure JPOXMLDOC01-appb-T000126
  Table 10
Figure JPOXMLDOC01-appb-T000126
（試験例５）
－ハスモンヨトウ（Ｓｐｏｄｏｐｔｅｒａ　ｌｉｔｕｒａ）に対する殺虫試験－
　試験化合物を所定濃度に調製した薬液にキャベツ葉片を３０秒間浸漬し風乾後、ろ紙を敷いた７ｃｍのポリエチレンカップに入れハスモンヨトウ２齢幼虫５頭を放虫した。２５℃恒温室にて静置し、６日後に生死虫数を調査した。連制なし。 (Test Example 5)
-Insecticidal test against Spodoptera litura-
Cabbage leaf pieces were immersed in a chemical solution prepared with a predetermined concentration of the test compound for 30 seconds and air-dried, and then placed in a 7 cm polyethylene cup with filter paper spread, and 5 second-instar larvae of the Japanese pearl moth were released. It left still in a 25 degreeC thermostat, and the number of live and dead insects was investigated 6 days afterward. No regime.
　上記試験の結果、試験化合物（化合物番号Ａ－０１６、Ｂ－００３、Ｃ－００１、Ｃ－００６）が濃度１０００ｐｐｍで７０％以上の死虫率を示した。 As a result of the above test, the test compounds (Compound Nos. A-016, B-003, C-001, C-006) showed a death rate of 70% or more at a concentration of 1000 ppm.
（試験例６）
－コナガ（Ｐｌｕｔｅｌｌａ　ｘｙｌｏｓｔｅｌｌａ）に対する殺虫試験－
　試験化合物を所定濃度に調製した薬液にキャベツ葉片を３０秒間浸漬し風乾後、ろ紙を敷いた７ｃｍのポリエチレンカップに入れコナガ３齢幼虫５頭を放虫した。２５℃恒温室にて静置し、６日後に生死虫数を調査した。連制なし。 (Test Example 6)
-Insecticidal test against blue moth (Plutella xylostella)-
Cabbage leaf pieces were immersed in a chemical solution prepared with a predetermined concentration of the test compound for 30 seconds and air-dried, and then placed in a 7 cm polyethylene cup with filter paper and five third-instar larvae were released. It left still in a 25 degreeC thermostat, and the number of live and dead insects was investigated 6 days afterward. No regime.
　上記試験の結果、化合物番号Ａ－０１６、Ａ－０４１、Ａ－０４２、Ａ－０４４、Ａ－０６２、Ｂ－００３、Ｃ－００６の化合物が濃度１０００ｐｐｍで７０％以上の死虫率を示した。 As a result of the above test, the compound Nos. A-016, A-041, A-042, A-044, A-062, B-003, and C-006 showed a death rate of 70% or more at a concentration of 1000 ppm. .
（試験例７）
－イエバエ（Ｍｕｓｃａ　ｄｏｍｅｓｔｉｃａ）に対する殺虫試験－
　試験化合物を所定濃度に調製したアセトン溶液１ｍｌを直径９ｃｍの腰高シャーレに滴下し風乾後、イエバエ雌成虫５頭を放虫し蓋をした。２５℃恒温室にて静置し、１日後に生死虫数を調査した。連制なし。 (Test Example 7)
-Insecticidal test against houseflies (Musca domestica)-
1 ml of an acetone solution prepared with a test compound at a predetermined concentration was dropped on a petri dish having a diameter of 9 cm and air-dried, and then 5 adult houseflies were released and capped. After leaving still in a constant temperature room at 25 ° C., the number of live and dead insects was examined one day later. No regime.
　上記試験の結果、化合物番号Ａ－００６、Ａ－０１６、Ａ－０３４、Ａ－０３５の化合物が濃度１０００ｐｐｍで７０％以上の死虫率を示した。　 As a result of the above test, the compound Nos. A-006, A-016, A-034, and A-035 showed a death rate of 70% or more at a concentration of 1000 ppm. *
　２０１３年１月３０日に出願された日本国特許出願２０１３－０１６１０１号の開示は、その全体が参照により本明細書に取り込まれる。
　本明細書に記載された全ての文献、特許出願、および技術規格は、個々の文献、特許出願、および技術規格が参照により取り込まれることが具体的かつ個々に記された場合と同程度に、本明細書中に参照により取り込まれる。 The disclosure of Japanese Patent Application No. 2013-016101 filed on January 30, 2013 is incorporated herein by reference in its entirety.
All documents, patent applications, and technical standards mentioned in this specification are to the same extent as if each individual document, patent application, and technical standard were specifically and individually described to be incorporated by reference, Incorporated herein by reference.

Claims (12)

  1. 　　下記一般式（Ｉ）
    Figure JPOXMLDOC01-appb-C000001
    ｛一般式（Ｉ）中、
    　Ｇ１は、窒素原子、炭素原子、又はＣＨを表す。
    　Ｒ１は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１－Ｃ６アルキル基、Ｃ２－Ｃ６アルケニル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、又はＣ１－Ｃ６ハロアルキルスルホニル基を表す。
    　ｍは、１～３の整数を表し、ｍが２以上の整数を表すとき、各々のＲ１はお互いに同一であっても、相異なってもよい。
    　ｎは、０又は１を表す。
    　Ｈｙは、下記一般式（Ｂ０）
    Figure JPOXMLDOC01-appb-C000002
    で表される５員環又は６員環の芳香族環を表す（＊２はＧ２への結合位置を表す）。
    　ここで、Ａ１は、炭素原子又は窒素原子を表す。
    　Ａ２は、炭素原子又は硫黄原子を表す。
    　Ａ３は、炭素原子又は窒素原子を表す。
    　Ａ４は、炭素原子又は窒素原子を表す。
     
    　ただし、Ａ１とＡ２が共に炭素原子であることはない。
    　ｐは、０～２の整数を表す。
    　ｑは、０又は１を表す。
    　Ｒ２は、水素原子、ハロゲン原子、Ｃ１－Ｃ６アルキル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、又は、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルホニル基、ヒドロキシアミノ基、アシルヒドラジニル基、若しくは置換されていてもよいイミダゾイル基で置換されたＣ１－Ｃ６アルキル基を表す。
    　Ｇ２は、下記一般式（Ｉ－Ｇ２）
    Figure JPOXMLDOC01-appb-C000003
    で表される置換基である（＊１はＨｙへの結合位置を表す）。
    　ここで、Ｑは、酸素原子、又はＮＲ５を表す。
    　Ｒ５は、水素原子、Ｃ１－Ｃ６アルキル基、Ｃ３－Ｃ６シクロアルキル基、Ｃ２－Ｃ６アルケニル基、Ｃ２－Ｃ６アルキニル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、Ｃ１－Ｃ６アルコキシカルボニル基、Ｃ１－Ｃ６アルキルカルボニル基、Ｃ１－Ｃ６アルキルアミノカルボニル基、又はジ（Ｃ１－Ｃ６アルキル）アミノカルボニル基を表す。
    　Ｒ３は、水素原子、Ｃ１－Ｃ６アルキル基、Ｃ３－Ｃ６シクロアルキル基、Ｃ２－Ｃ６アルケニル基、Ｃ２－Ｃ６アルキニル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、Ｃ1－Ｃ６アルコキシカルボニル基、ホルミル基、Ｃ1－Ｃ６アルキルカルボニル基、Ｃ１－Ｃ６アルキルアミノカルボニル基又はジ（Ｃ１－Ｃ６アルキル）アミノカルボニル基、又はＣ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、若しくはＣ１－Ｃ６ハロアルキルスルホニル基で置換されたＣ１－Ｃ６アルキル基を表す。
    　Ｒ２とＲ３は互いに結合して５員環又は６員環を形成していてもよい。
    　Ｒ４は、Ｃ１－Ｃ６アルキル基、Ｃ３－Ｃ６シクロアルキル基、Ｃ２－Ｃ６アルケニル基、Ｃ２－Ｃ６アルキニル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、Ｃ1－Ｃ６アルコキシカルボニル基、Ｃ1－Ｃ６ハロアルコキシカルボニル基、Ｃ1－Ｃ６アルキルカルボニル基、Ｃ1－Ｃ６ハロアルキルカルボニル基、Ｃ１－Ｃ６アルキルアミノカルボニル基、置換されていてもよいフェニルアミノカルボニル基、Ｃ１－Ｃ６ハロアルキルアミノカルボニル基、ジ（Ｃ１－Ｃ６アルキル）アミノカルボニル基、（Ｃ１－Ｃ６アルキル）（Ｃ１－Ｃ６ハロアルキル）アミノカルボニル基、ジ（Ｃ１－Ｃ６ハロアルキル）アミノカルボニル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、置換されていてもよいベンゾイル基、置換されていてもよいＣ１－Ｃ６アルキル基、置換されていてもよいＣ１－Ｃ６ハロアルキル基、置換されていてもよいＣ１－Ｃ６アルキルカルボニル基、置換されていてもよいＣ１－Ｃ６ハロアルキルカルボニル基、置換されていてもよいＣ１－Ｃ６アルコキシカルボニル基、置換されていてもよいＣ１－Ｃ６ハロアルコキシカルボニル基、置換されていてもよいＣ１－Ｃ６アルキルアミノカルボニル基、置換されていてもよいＣ１－Ｃ６ハロアルキルアミノカルボニル基を表すか、
    または、Ｒ４は、置換されていてもよいヘテロシクリル基、置換されていてもよいフラニル基、置換されていてもよいチエニル基、置換されていてもよいピロリル基、置換されていてもよいピラゾリル基、置換されていてもよいイミダゾリル基、置換されていてもよい１，２，３－トリアゾリル基、置換されていてもよい１，２，４－トリアゾリル基、置換されていてもよいオキサゾリル基、置換されていてもよいイソオキサゾリル基、置換されていてもよいチアゾリル基、置換されていてもよいイソチアゾリル基、置換されていてもよい１，２，３－オキサジアゾリル基、置換されていてもよい１，２，４－オキサジアゾリル基、置換されていてもよい１，３，４－オキサジアゾリル基、置換されていてもよい１，２，５－オキサジアゾリル基、置換されていてもよい１，２，３－チアジアゾリル基、置換されていてもよい１，２，４－チアジアゾリル基、置換されていてもよい１，３，４－チアジアゾリル、置換されていてもよい１，２，５－チアジアゾリル基、置換されていてもよいピリジル基、置換されていてもよいピリミジニル基、置換されていてもよいピリダジニル基、置換されていてもよいピラジニル基、置換されていてもよい１，２，３－トリアジニル基、置換されていてもよい１，２，４－トリアジニル基、置換されていてもよい１，３，５－トリアジニル基、置換されていてもよいベンゾフリル基、置換されていてもよいベンゾイソフリル基、置換されていてもよいベンゾチエニル基、置換されていてもよいベンゾイソチエニル基、置換されていてもよいインドリル基、置換されていてもよいイソインドリル基、置換されていてもよいインダゾリル基、置換されていてもよいベンゾチアゾリル基、置換されていてもよいベンゾイソチアゾリル基、置換されていてもよいベンゾオキサゾリル基、置換されていてもよいベンゾイソオキサゾリル基、置換されていてもよいベンゾイミダゾリル基、置換されていてもよい２，１，３－ベンゾオキサジアゾール基、置換されていてもよいキノリニル基、置換されていてもよいイソキノリニル基、置換されていてもよいシンノリニル基、置換されていてもよいフタラジニル基、置換されていてもよいキナゾリニル基、置換されていてもよいキノキサリニル基、置換されていてもよいナフチリジニル基、置換されていてもよいベンゾトリアジニル基、置換されていてもよいプリニル基、置換されていてもよいプテリジニル基、置換されていてもよいインドリジニル基、又はシアノ基、ニトロ基、ハロアルコキシ基、若しくはヘテロシクリル基で置換されているアリール基を表す。
    　ただし、Ａ１が窒素原子かつＡ２が硫黄原子かつＱが酸素原子かつｎが０の場合、Ｒ４は置換されていてもよいヘテロシクリル基、置換されていてもよいフラニル基、置換されていてもよいチエニル基、置換されていてもよいピロリル基、置換されていてもよいピラゾリル基、置換されていてもよいイミダゾリル基、置換されていてもよい１，２，３－トリアゾリル基、置換されていてもよい１，２，４－トリアゾリル基、置換されていてもよいオキサゾリル基、置換されていてもよいイソオキサゾリル基、置換されていてもよいチアゾリル基、置換されていてもよいイソチアゾリル基、置換されていてもよい１，２，３－オキサジアゾリル基、置換されていてもよい１，２，４－オキサジアゾリル基、置換されていてもよい１，３，４－オキサジアゾリル基、置換されていてもよい１，２，５－オキサジアゾリル基、置換されていてもよい１，２，３－チアジアゾリル基、置換されていてもよい１，２，４－チアジアゾリル基、置換されていてもよい１，３，４－チアジアゾリル、置換されていてもよい１，２，５－チアジアゾリル基、置換されていてもよいピリジル基、置換されていてもよいピリミジニル基、置換されていてもよいピリダジニル基、置換されていてもよいピラジニル基、置換されていてもよい１，２，３－トリアジニル基、置換されていてもよい１，２，４－トリアジニル基、置換されていてもよい１，３，５－トリアジニル基、置換されていてもよいベンゾフリル基、置換されていてもよいベンゾイソフリル基、置換されていてもよいベンゾチエニル基、置換されていてもよいベンゾイソチエニル基、置換されていてもよいインドリル基、置換されていてもよいイソインドリル基、置換されていてもよいインダゾリル基、置換されていてもよいベンゾチアゾリル基、置換されていてもよいベンゾイソチアゾリル基、置換されていてもよいベンゾオキサゾリル基、置換されていてもよいベンゾイソオキサゾリル基、置換されていてもよいベンゾイミダゾリル基、置換されていてもよい２，１，３－ベンゾオキサジアゾール基、置換されていてもよいキノリニル基、置換されていてもよいイソキノリニル基、置換されていてもよいシンノリニル基、置換されていてもよいフタラジニル基、置換されていてもよいキナゾリニル基、置換されていてもよいキノキサリニル基、置換されていてもよいナフチリジニル基、置換されていてもよいベンゾトリアジニル基、置換されていてもよいプリニル基、置換されていてもよいプテリジニル基及びインドリジニル基、又はシアノ基、ニトロ基、ハロアルコキシ基、若しくはヘテロシクリル基で置換されているアリール基であることはない。
    　また、Ａ１が窒素原子かつＡ２が硫黄原子かつＡ３が炭素原子かつＲ２がメチル基かつＱがＮＲ５かつＲ５が水素原子の場合、Ｒ４はメトキシカルボニル基であることはない。｝
    で表される、複素環化合物又はその塩。     The following general formula (I)
    Figure JPOXMLDOC01-appb-C000001
    {In general formula (I),
    G 1 represents a nitrogen atom, a carbon atom, or CH.
    R 1 is a hydrogen atom, halogen atom, cyano group, nitro group, C1-C6 alkyl group, C2-C6 alkenyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 An alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 haloalkylsulfonyl group is represented.
    m represents an integer of 1 to 3, and when m represents an integer of 2 or more, each R 1 may be the same as or different from each other.
    n represents 0 or 1.
    Hy represents the following general formula (B0)
    Figure JPOXMLDOC01-appb-C000002
    Represents a 5-membered or 6-membered aromatic ring represented by the formula (* 2 represents a bonding position to G2).
    Here, A 1 represents a carbon atom or a nitrogen atom.
    A 2 represents a carbon atom or a sulfur atom.
    A 3 represents a carbon atom or a nitrogen atom.
    A 4 represents a carbon atom or a nitrogen atom.

    However, A 1 and A 2 are not both carbon atoms.
    p represents an integer of 0 to 2.
    q represents 0 or 1;
    R 2 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1- C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, or C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 It represents a C1-C6 alkyl group substituted with an alkylsulfonyl group, a hydroxyamino group, an acyl hydrazinyl group, or an optionally substituted imidazolyl group.
    G 2 represents the following general formula (IG 2 )
    Figure JPOXMLDOC01-appb-C000003
    (* 1 represents the bonding position to Hy).
    Here, Q represents an oxygen atom or NR 5 .
    R 5 is a hydrogen atom, C1-C6 alkyl group, C3-C6 cycloalkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 haloalkyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl Group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylcarbonyl group, a C1-C6 alkylaminocarbonyl group, or a di (C1-C6 alkyl) aminocarbonyl group.
    R 3 is a hydrogen atom, C1-C6 alkyl group, C3-C6 cycloalkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkoxycarbonyl group, formyl Group, C1-C6 alkylcarbonyl group, C1-C6 alkylaminocarbonyl group or di (C1-C6 alkyl) aminocarbonyl group, or C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1- A C6 alkylsulfinyl group, 1-C6 alkylsulfonyl group, a C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, or a C1-C6 alkyl group substituted with a C1-C6 haloalkylsulfonyl group.
    R 2 and R 3 may be bonded to each other to form a 5-membered ring or a 6-membered ring.
    R 4 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C6 haloalkyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1 -C6 alkoxycarbonyl group, C1-C6 haloalkoxycarbonyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkylaminocarbonyl group, optionally substituted phenylaminocarbonyl group, C1-C6 Haloalkylaminocarbonyl group, di (C1-C6 alkyl) aminocarbonyl group, (C1-C6 alkyl) (C1-C6 haloalkyl) aminocarbonyl group, di (C1-C6 haloalkyl) aminocarbonyl group, C1-C6 alkoxy group, C1 -C6 haloal Xi group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, optionally substituted benzoyl group, optionally substituted C1-C6 alkyl group An optionally substituted C1-C6 haloalkyl group, an optionally substituted C1-C6 alkylcarbonyl group, an optionally substituted C1-C6 haloalkylcarbonyl group, an optionally substituted C1-C6 alkoxycarbonyl group A group, an optionally substituted C1-C6 haloalkoxycarbonyl group, an optionally substituted C1-C6 alkylaminocarbonyl group, an optionally substituted C1-C6 haloalkylaminocarbonyl group,
    Or R 4 represents an optionally substituted heterocyclyl group, an optionally substituted furanyl group, an optionally substituted thienyl group, an optionally substituted pyrrolyl group, or an optionally substituted pyrazolyl group; Optionally substituted imidazolyl group, optionally substituted 1,2,3-triazolyl group, optionally substituted 1,2,4-triazolyl group, optionally substituted oxazolyl group, substituted An optionally substituted isoxazolyl group, an optionally substituted thiazolyl group, an optionally substituted isothiazolyl group, an optionally substituted 1,2,3-oxadiazolyl group, an optionally substituted 1,2 1,4-oxadiazolyl group, 1,3,4-oxadiazolyl group which may be substituted, 1,2,5-oxadiazolyl group which may be substituted Group, optionally substituted 1,2,3-thiadiazolyl group, optionally substituted 1,2,4-thiadiazolyl group, optionally substituted 1,3,4-thiadiazolyl group, substituted 1,2,5-thiadiazolyl group which may be substituted, pyridyl group which may be substituted, pyrimidinyl group which may be substituted, pyridazinyl group which may be substituted, pyrazinyl group which may be substituted, substituted 1,2,3-triazinyl group which may be substituted, 1,2,4-triazinyl group which may be substituted, 1,3,5-triazinyl group which may be substituted, benzofuryl which may be substituted A group, an optionally substituted benzoisofuryl group, an optionally substituted benzothienyl group, an optionally substituted benzoisothienyl group, an optionally substituted indium Ryl group, optionally substituted isoindolyl group, optionally substituted indazolyl group, optionally substituted benzothiazolyl group, optionally substituted benzisothiazolyl group, optionally substituted benzoxa A zolyl group, an optionally substituted benzisoxazolyl group, an optionally substituted benzimidazolyl group, an optionally substituted 2,1,3-benzoxadiazole group, an optionally substituted A quinolinyl group, an optionally substituted isoquinolinyl group, an optionally substituted cinnolinyl group, an optionally substituted phthalazinyl group, an optionally substituted quinazolinyl group, an optionally substituted quinoxalinyl group, a substituted Optionally substituted naphthyridinyl group, optionally substituted benzotriazinyl group, substituted Which may purinyl group, an optionally substituted pteridinyl group, an optionally substituted indolizinyl group, or a cyano group, a nitro group, a haloalkoxy group, or an aryl group substituted with a heterocyclyl group.
    However, when A 1 is a nitrogen atom, A 2 is a sulfur atom, Q is an oxygen atom, and n is 0, R 4 is an optionally substituted heterocyclyl group, an optionally substituted furanyl group, An optionally substituted thienyl group, an optionally substituted pyrrolyl group, an optionally substituted pyrazolyl group, an optionally substituted imidazolyl group, an optionally substituted 1,2,3-triazolyl group, a substituted 1,2,4-triazolyl group which may be substituted, oxazolyl group which may be substituted, isoxazolyl group which may be substituted, thiazolyl group which may be substituted, isothiazolyl group which may be substituted, substituted 1,2,3-oxadiazolyl group which may be substituted, 1,2,4-oxadiazolyl group which may be substituted, 1,3,4-optionally substituted Oxadiazolyl group, optionally substituted 1,2,5-oxadiazolyl group, optionally substituted 1,2,3-thiadiazolyl group, optionally substituted 1,2,4-thiadiazolyl group, substituted 1,3,4-thiadiazolyl which may be substituted, 1,2,5-thiadiazolyl which may be substituted, pyridyl which may be substituted, pyrimidinyl which may be substituted, A good pyridazinyl group, an optionally substituted pyrazinyl group, an optionally substituted 1,2,3-triazinyl group, an optionally substituted 1,2,4-triazinyl group, an optionally substituted 1 , 3,5-triazinyl group, optionally substituted benzofuryl group, optionally substituted benzoisofuryl group, optionally substituted benzothienyl group, Benzoisothienyl group which may be substituted, indolyl group which may be substituted, isoindolyl group which may be substituted, indazolyl group which may be substituted, benzothiazolyl group which may be substituted, substituted Optionally substituted benzoisothiazolyl group, optionally substituted benzoxazolyl group, optionally substituted benzisoxazolyl group, optionally substituted benzimidazolyl group, optionally substituted 2 1,3-Benzoxadiazole group, optionally substituted quinolinyl group, optionally substituted isoquinolinyl group, optionally substituted cinnolinyl group, optionally substituted phthalazinyl group, substituted Quinazolinyl group which may be substituted, quinoxalinyl group which may be substituted, naphthyl which may be substituted A dinyl group, an optionally substituted benzotriazinyl group, an optionally substituted purinyl group, an optionally substituted pteridinyl group and indolizinyl group, or a cyano group, a nitro group, a haloalkoxy group, or a heterocyclyl group It is not an aryl group substituted with.
    When A 1 is a nitrogen atom, A 2 is a sulfur atom, A 3 is a carbon atom, R 2 is a methyl group, Q is NR 5 and R 5 is a hydrogen atom, R 4 is not a methoxycarbonyl group. . }
    The heterocyclic compound or its salt represented by these.
  2. 　Ｈｙが、下記式（Ｂ１）から式（Ｂ１１）のいずれかを表す、
    Figure JPOXMLDOC01-appb-C000004
    　｛上記式（Ｂ１）から式（Ｂ１１）中、
    　Ｒ２は、水素原子、ハロゲン原子、Ｃ１－Ｃ６アルキル基、Ｃ１－Ｃ６ハロアルキル基、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルフィニル基、Ｃ１－Ｃ６アルキルスルホニル基、Ｃ１－Ｃ６ハロアルキルチオ基、Ｃ１－Ｃ６ハロアルキルスルフィニル基、Ｃ１－Ｃ６ハロアルキルスルホニル基、又は、Ｃ１－Ｃ６アルコキシ基、Ｃ１－Ｃ６ハロアルコキシ基、Ｃ１－Ｃ６アルキルチオ基、Ｃ１－Ｃ６アルキルスルホニル基、ヒドロキシアミノ基、アシルヒドラジニル基、若しくは置換されていてもよいイミダゾイル基で置換されたＣ１－Ｃ６アルキル基を表す。
    　＊２はＧ２への結合位置を表す。｝
    請求項１に記載の複素環化合物又はその塩。     Hy represents one of the following formulas (B 1 ) to (B 11 ):
    Figure JPOXMLDOC01-appb-C000004
    {From the above formula (B 1 ) to formula (B 11 )
    R 2 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1- C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, or C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 It represents a C1-C6 alkyl group substituted with an alkylsulfonyl group, a hydroxyamino group, an acyl hydrazinyl group, or an optionally substituted imidazolyl group.
    * 2 represents a bonding position to G 2. }
    The heterocyclic compound of Claim 1 or its salt.
  3. 　ＱがＮＲ５を表す、請求項２に記載の複素環化合物又はその塩。 The heterocyclic compound or a salt thereof according to claim 2, wherein Q represents NR 5 .
  4. 　ＱがＮＲ５を表し、Ｈｙが、下記式（Ｂ１）、（Ｂ２）、（Ｂ４）、（Ｂ５）、（Ｂ６）、（Ｂ７）、（Ｂ８）又は（Ｂ９）を表す
    Figure JPOXMLDOC01-appb-C000005
    　｛上記式（Ｂ１）、（Ｂ２）、（Ｂ４）、（Ｂ５）、（Ｂ６）、（Ｂ７）、（Ｂ８）及び（Ｂ９）中
    　Ｒ２は、前記と同様の意味を表し、＊２はＧ２への結合位置を表す。｝
    　請求項３に記載の複素環化合物又はその塩。     Q represents NR 5 and Hy represents the following formula (B 1 ), (B 2 ), (B 4 ), (B 5 ), (B 6 ), (B 7 ), (B 8 ) or (B 9 ). Represents
    Figure JPOXMLDOC01-appb-C000005
    {In the above formulas (B 1 ), (B 2 ), (B 4 ), (B 5 ), (B 6 ), (B 7 ), (B 8 ) and (B 9 ), R 2 is the same as above the meaning of, * 2 denotes the point of attachment to G 2. }
    The heterocyclic compound or salt thereof according to claim 3.
  5. 　Ｑが酸素原子を表す、請求項２に記載の複素環化合物又はその塩。 The heterocyclic compound or a salt thereof according to claim 2, wherein Q represents an oxygen atom.
  6. 　Ｑが酸素原子を表し、Ｈｙが、下記式（Ｂ１）、（Ｂ２）、（Ｂ４）、（Ｂ５）、（Ｂ６）、（Ｂ７）、（Ｂ８）又は（Ｂ９）を表す
    Figure JPOXMLDOC01-appb-C000006
    　｛上記式（Ｂ１）、（Ｂ２）、（Ｂ４）、（Ｂ５）、（Ｂ６）、（Ｂ７）、（Ｂ８）及び（Ｂ９）中
    　Ｒ２は、前記と同様の意味を表し、＊２はＧ２への結合位置を表す。｝
    　請求項５に記載の複素環化合物又はその塩。     Q represents an oxygen atom, and Hy represents the following formula (B 1 ), (B 2 ), (B 4 ), (B 5 ), (B 6 ), (B 7 ), (B 8 ) or (B 9 ). Represents
    Figure JPOXMLDOC01-appb-C000006
    {In the above formulas (B 1 ), (B 2 ), (B 4 ), (B 5 ), (B 6 ), (B 7 ), (B 8 ) and (B 9 ), R 2 is the same as above the meaning of, * 2 denotes the point of attachment to G 2. }
    The heterocyclic compound or salt thereof according to claim 5.
  7. 　請求項１から請求項６のいずれか１項に記載の複素環化合物又はその塩と、不活性担体又は補助剤と、を含む組成物。 A composition comprising the heterocyclic compound or a salt thereof according to any one of claims 1 to 6, and an inert carrier or adjuvant.
  8. 　請求項１から請求項６のいずれか１項に記載の複素環化合物又はその塩を有効成分として含有する有害生物防除剤。 A pest control agent comprising the heterocyclic compound according to any one of claims 1 to 6 or a salt thereof as an active ingredient.
  9. 　請求項１から請求項６のいずれか１項に記載の複素環化合物又はその塩を有効成分として含有する農園芸用有害生物防除剤。 An agricultural and horticultural pest control agent comprising the heterocyclic compound or salt thereof according to any one of claims 1 to 6 as an active ingredient.
  10. 　請求項１から請求項６のいずれか１項に記載の複素環化合物又はその塩の有効量を含む薬剤を、有用作物又は土壌に処理することを含む前記薬剤の使用方法。 A method for using the drug comprising treating a useful crop or soil with a drug containing an effective amount of the heterocyclic compound or salt thereof according to any one of claims 1 to 6.
  11. 　請求項１から請求項６のいずれか１項に記載の複素環化合物又はその塩と、前記複素環化合物又はその塩とは異なる、他の殺虫剤及び／又は殺菌剤のうち１種以上と、を含む混合物。 The heterocyclic compound or salt thereof according to any one of claims 1 to 6, and at least one of other insecticides and / or fungicides different from the heterocyclic compound or salt thereof, Containing mixture.
  12. 　請求項１から請求項６のいずれか１項に記載の複素環化合物又はその塩の有効量を含む薬剤を、有用作物又は土壌に処理することを含む、有害生物防除方法。 A method for controlling pests, comprising treating a useful crop or soil with a drug containing an effective amount of the heterocyclic compound or salt thereof according to any one of claims 1 to 6.
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