WO2019065568A1 - Heterocyclic compound and harmful arthropod-controlling agent containing same - Google Patents

Heterocyclic compound and harmful arthropod-controlling agent containing same Download PDF

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Publication number
WO2019065568A1
WO2019065568A1 PCT/JP2018/035296 JP2018035296W WO2019065568A1 WO 2019065568 A1 WO2019065568 A1 WO 2019065568A1 JP 2018035296 W JP2018035296 W JP 2018035296W WO 2019065568 A1 WO2019065568 A1 WO 2019065568A1
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group
compound
formula
present
virus
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PCT/JP2018/035296
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French (fr)
Japanese (ja)
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亮太 前畑
中嶋　祐二
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住友化学株式会社
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Priority claimed from JP2017245958A external-priority patent/JP2021006508A/en
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Publication of WO2019065568A1 publication Critical patent/WO2019065568A1/en

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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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • C07D213/79—Acids; Esters
    • 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
    • C07D213/84—Nitriles
    • 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
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Definitions

  • An object of the present invention is to provide a compound having excellent control efficacy against harmful arthropods.
  • the compound represented by the following formula (I) has an excellent control activity against harmful arthropods Found out. That is, the present invention is as follows. [1] Formula (I): [In the formula, A 1 represents NCH 3 , an oxygen atom or a sulfur atom, A 2 represents a nitrogen atom or CH, R 1 represents a C1 to C3 perfluoroalkyl group, a C1 to C3 perfluoroalkoxy group, a C1 to C3 perfluoroalkylsulfanyl group, a C1 to C3 perfluoroalkylsulfinyl group, or a C1 to C3 perfluoroalkylsulfonyl group, R 2 is a C2-C5 chain hydrocarbon group which may have one or more halogen atoms, (C1-C2 alkoxy) C1-C2 alkyl group which may have
  • R 2 is a C2-C3 chain hydrocarbon group optionally having one or more halogen atoms, a cyclopropyl group optionally having one or more substituents selected from Group X, or The compound according to [1], which is a (cyclopropyl) methyl group which may have one or more substituents selected from Group X.
  • a combination of A 1 and A 2 is a combination in which A 1 is NCH 3 and A 2 is a nitrogen atom, or a combination in which A 1 is an oxygen atom and A 2 is CH [ The compound as described in any one of 1] to [3].
  • a 1 is NCH 3 and A 2 is a nitrogen atom.
  • a harmful arthropod controlling composition comprising the compound according to any one of [1] to [6] and an inert carrier.
  • a method for controlling noxious arthropods which comprises applying an effective amount of the compound according to any one of [1] to [6] to a harmful arthropod or a habitat of the harmful arthropod.
  • composition Mark as "A" A composition containing one or more components selected from the group consisting of group (a) and group (b), and the compound according to any one of [1] to [6] (hereinafter referred to as “composition Mark as "A”): Group (a): a group consisting of an insecticidal active ingredient, an acaricidal active ingredient and a nematode active ingredient; Group (b): bactericidal active ingredient.
  • R x represents OR 2 , a fluorine atom or a chlorine atom
  • R 2 is a C2-C5 chain hydrocarbon group which may have one or more halogen atoms, (C1-C2 alkoxy) C1-C2 alkyl group which may have one or more halogen atoms, a group A cyclopropyl group which may have one or more substituents selected from X, or (a cyclopropyl group optionally having one or more substituents selected from group X) C1-C2 alkyl group, n represents 0, 1 or 2; R y represents a cyano group, a carboxy group, a methoxycarbonyl group or an ethoxycarbonyl group.
  • Group X a group consisting of a cyano group and a halogen atom.
  • Compound (Hereinafter, it is described as "intermediate X") shown.
  • [11] A method for controlling noxious arthropods, which comprises applying an effective amount of the composition according to [7] or [9] to a harmful arthropod or a habitat of the harmful arthropod.
  • [12] A seed or vegetative organ which retains an effective amount of the compound according to any one of [1] to [6] or an effective amount of the composition according to [7] or [9].
  • harmful arthropods can be controlled.
  • the compound represented by the formula (I) can be produced, for example, using the compound represented by the formula (X) as an intermediate.
  • the substituents in the present invention will be described.
  • the "halogen atom” means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. When the substituent has two or more halogen atoms, those halogen atoms may be the same or different.
  • the notation “CX-CY” in the present specification means that the number of carbon atoms is X to Y.
  • the notation “C1-C6” means that the number of carbon atoms is 1 to 6.
  • the “chain hydrocarbon group” represents an alkyl group, an alkenyl group or an alkynyl group.
  • alkyl group for example, methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, sec-butyl group, A tert-butyl group and a pentyl group can be mentioned.
  • alkenyl group for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1-methyl-2-propenyl group, 1-ethyl-2-propenyl group, 3-butenyl group and 4-pentenyl group can be mentioned.
  • alkynyl group for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, Examples include 2-butynyl group, 3-butynyl group, and 4-pentynyl group.
  • alkoxy group means a monovalent group in which an alkyl group is bonded to an oxygen atom, and examples thereof include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group and a hexyloxy group.
  • the “C2-C5 chain hydrocarbon group optionally having one or more halogen atoms” is one or more in addition to the groups exemplified as the above “alkyl group”, “alkenyl group” and “alkynyl group” And a C2-C5 chain hydrocarbon group having a halogen atom of As a C2-C5 chain hydrocarbon group having one or more halogen atoms, for example, 1,1-dimethyl-2,2,2-trifluoroethyl group, 2,2,3,3,3-pentafluoropropyl group 2,2,3,3-tetrafluoropropyl, 2,2,3,4,4,4-hexafluorobutyl)), 2,2,3,3,4,4,4-heptafluorobutyl Group, 4,4,4-trifluorobutyl group, 2,2,2-trifluoro-1-methylpropyl group, 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 2,2-diflu
  • C1-C3 perfluoroalkyl group examples include trifluoromethyl group, pentafluoroethyl group, and heptafluoropropyl group.
  • C 1 -C 3 perfluoroalkoxy group for example, trifluoromethoxy group, pentafluoroethoxy group, and heptafluoropropoxy group can be obtained.
  • C1-C3 perfluoroalkylsulfanyl group means, for example, a C1-C3 perfluoroalkyl having a portion represented by S (O) n.
  • examples of C1-C3 perfluoroalkylsulfanyl group in which n is 0 include, for example, trifluoromethylsulfanyl group, pentafluoroethylsulfanyl group, and heptafluoropropylsulfanyl group.
  • examples of the C1-C3 perfluoroalkylsulfinyl group in which n is 1 include, for example, trifluoromethylsulfinyl group, pentafluoroethylsulfinyl group, and heptafluoropropylsulfinyl group.
  • examples of the C1-C3 perfluoroalkylsulfonyl group in which n is 2 include, for example, trifluoromethylsulsulfonyl group, pentafluoroethylsulfonyl group, and heptafluoropropylsulfonyl group.
  • the "(C1-C2 alkoxy) C1-C2 alkyl group which may have one or more halogen atoms” means a halogen atom in which (C1-C2 alkoxy) and / or (C1-C2 alkyl group) is one or more For example, a methoxymethyl group, a methoxyethyl group, a 2-trifluoromethoxyethyl group, a 1-ethoxyethyl group, a 2,2-difluoro-2-ethoxyethyl group, and And 2-difluoro-2-trifluoromethoxyethyl group.
  • Examples of the “cyclopropyl group optionally having one or more substituents selected from group X” include cyclopropyl group, 1-cyanocyclopropyl group, and 2,2-difluorocyclopropyl group.
  • “((Cyclopropyl which may have one or more substituents selected from group X) C1-C2 alkyl group” means cyclopropyl which may have one or more substituents selected from group X Represents a substituted C1-C2 alkyl group, for example, cyclopropylmethyl group, 1-cyclopropylethyl group, 2-cyclopropylethyl group, (1-cyanocyclopropyl) methyl group, and (2,2-difluorocyclo group) And a propyl) methyl group.
  • R 2 may have a C2-C3 chain hydrocarbon group optionally having one or more halogen atoms, and one or more substituents selected from Group X A compound which is a good cyclopropyl group or a (cyclopropyl) methyl group which may have one or more substituents selected from group X.
  • R 3 The compound according to aspect 2, wherein n is 2.
  • R 4 The compound of the present invention, wherein R 2 is a C2-C3 chain hydrocarbon group, a cyclopropyl group or a cyclopropylmethyl group.
  • R 2 may have a C2-C3 chain hydrocarbon group optionally having one or more halogen atoms, and one or more substituents selected from group X
  • n is 2.
  • Aspect 10 A compound according to aspect 6, wherein R 2 is a C2-C3 chain hydrocarbon group or a cyclopropylmethyl group. 11. The compound according to aspect 10, wherein n is 2.
  • Embodiment 12 A compound according to Embodiment 6, wherein R 2 is an ethyl group, a C3 chain hydrocarbon group, or a cyclopropylmethyl group. [13] The compound according to Aspect 12, wherein n is 2.
  • Aspect 14 A compound of the present invention wherein A 2 is a nitrogen atom.
  • Aspect 15 A compound of the present invention wherein A 2 is CH.
  • the compound of the present invention, wherein A 1 is NCH 3 .
  • Aspect 17 The compound of the present invention, wherein A 1 is NCH 3 and A 2 is a nitrogen atom.
  • Aspect 18 The compound of the present invention, wherein A 1 is an oxygen atom or a sulfur atom.
  • Aspect 19 The compound of the present invention, wherein A 1 is an oxygen atom or a sulfur atom, and A 2 is CH.
  • Aspect 20 The compound of the present invention, wherein A 1 is an oxygen atom.
  • Aspect 21 The compound of the present invention, wherein A 1 is an oxygen atom and A 2 is CH.
  • a 2 is a nitrogen atom in any of the modes 1 to 13.
  • Embodiment 23 The compound according to any of Embodiments 1 to 13, wherein A 2 is CH.
  • Aspect 25 A compound according to any of aspects 1 to 13, wherein A 1 is NCH 3 and A 2 is a nitrogen atom.
  • Aspect 26 The compound according to any of aspects 1 to 13, wherein A 1 is NCH 3 and A 2 is a nitrogen atom.
  • Aspect 27 The compound according to any of Aspects 1 to 13, wherein A 1 is an oxygen atom or a sulfur atom, and A 2 is CH. The compound of any one of aspects 1 to 13 wherein A 1 is an oxygen atom.
  • Aspect 29 The compound according to any of aspects 1 to 13, wherein A 1 is an oxygen atom and A 2 is CH.
  • Examples of production intermediates of the compound of the present invention include the following compounds.
  • R x is OR 2 , a fluorine atom or a chlorine atom
  • R 2 is a C 2 -C 5 chain hydrocarbon group which may have one or more halogen atoms, (C 1 -C 2 alkoxy) C 1 -C 2 alkyl group which may have one or more halogen atoms, a group A cyclopropyl group which may have one or more substituents selected from X, or (a cyclopropyl group optionally having one or more substituents selected from group X) C1-C2 alkyl group, n is 0, 1 or 2;
  • R y is a cyano group, a carboxy group, a methoxycarbonyl group or an ethoxycarbonyl group,
  • Group X a group consisting of a cyano group and a halogen atom
  • Embodiment 32. A compound according to embodiment 30, wherein R 2 is a C 2 -C 4 alkyl group or a cyclopropylmethyl group.
  • Aspect 33. A compound according to aspect 30, wherein R x is OR 2 and R 2 is a C2-C4 alkyl group or a cyclopropylmethyl group.
  • Aspect 34. A compound according to aspect 30, wherein R x is a fluorine atom or a chlorine atom.
  • Aspect 35. The compound according to any one of aspects 30 to 34, wherein R y is a cyano group.
  • R 2 may have a C2-C4 chain hydrocarbon group optionally having one or more halogen atoms, and one or more substituents selected from Group X A compound which is a cyclopropyl group or a (cyclopropyl group) methyl group which may have one or more substituents selected from group X;
  • Embodiment 40 A compound in which in the intermediate X, R 2 is a C2-C4 alkyl group or a cyclopropylmethyl group.
  • R x is OR 2 and R 2 is a C2-C4 alkyl group or a cyclopropylmethyl group.
  • Embodiment 42 A compound in which in the intermediate X, R x is a fluorine atom or a chlorine atom.
  • Aspect 43 A compound according to any one of aspects 39 to 42, wherein R y is a carboxy group, a methoxycarbonyl group or an ethoxycarbonyl group.
  • the compound represented by the formula (Ic) (hereinafter referred to as the compound (Ic)) is a compound represented by the formula (Ia) (hereinafter referred to as the compound (Ia)) or the formula (Ic) It can manufacture by oxidizing the compound (It is hereafter described as a compound (Ib)) shown by -b).
  • Compound (Ib) can be produced by oxidizing compound (Ia). [Wherein, the symbols have the same meanings as described above. ] First, a method for producing compound (Ib) from compound (Ia) is described. The reaction is usually carried out in a solvent.
  • halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as halogenated hydrocarbons); nitriles such as acetonitrile (hereinafter referred to as nitriles); alcohols such as methanol and ethanol Hereinafter, it is described as an alcohol); acetic acid; water and a mixture of two or more of them.
  • oxidizing agent used for the reaction include sodium periodate, m-chloroperbenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide. When using hydrogen peroxide as an oxidizing agent, you may add a base or a catalyst as needed.
  • Sodium carbonate is mentioned as a base used for reaction.
  • tungstic acid and sodium tungstate are mentioned, for example.
  • the oxidizing agent is usually used in a proportion of 1 to 1.2 mol per 1 mol of the compound (Ia).
  • the base is usually used in a proportion of 0.01 to 1 mole per 1 mole of the compound (Ia).
  • the catalyst is usually used in a proportion of 0.01 to 0.5 mol per 1 mol of compound (Ia).
  • the reaction temperature is usually in the range of -20 to 80 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • the compound (Ib) can be obtained by washing and drying and concentration of the obtained organic layer.
  • a reducing agent eg sodium sulfite, sodium thiosulfate
  • a base eg sodium hydrogencarbonate
  • the reaction is usually carried out in a solvent.
  • a solvent used for reaction halogenated hydrocarbons, nitriles, alcohols, an acetic acid, water, and the mixture of 2 or more types of these are mentioned, for example.
  • the oxidizing agent used for the reaction include mCPBA and hydrogen peroxide.
  • hydrogen peroxide As an oxidizing agent, you may add a base or a catalyst as needed.
  • Sodium carbonate is mentioned as a base used for reaction.
  • sodium tungstate is mentioned, for example.
  • an oxidizing agent is usually used at a ratio of 1 to 2 moles relative to 1 mole of the compound (Ib).
  • the base is usually used in a proportion of 0.01 to 1 mole per 1 mole of the compound (Ib).
  • a catalyst is used in the reaction, the catalyst is usually used in a proportion of 0.01 to 0.5 mol per 1 mol of compound (Ib).
  • the reaction temperature is usually in the range of -20 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • the compound (Ic) can be obtained by washing and drying and concentration of the obtained organic layer.
  • a reducing agent eg sodium sulfite, sodium thiosulfate
  • a base eg sodium hydrogencarbonate
  • compound (Ic) can be produced by a one-step reaction (one pot) by reacting compound (Ia) with an oxidizing agent.
  • the reaction is carried out according to the method for producing compound (Ic) from compound (Ib), using an oxidizing agent in a proportion of usually 2 to 5 moles relative to 1 mole of compound (Ia). Can.
  • the compound of the present invention is a compound represented by the formula (M-1) (hereinafter referred to as a compound (M-1)) and a compound represented by the formula (R-1) (hereinafter referred to as a compound (R-1)) Can be produced by reacting in the presence of a base.
  • M-1 a compound represented by the formula (M-1)
  • R-1 a compound represented by the formula (R-1)
  • M-1 a compound represented by the formula (R-1)
  • X a represents a bromine atom or an iodine atom, and the other symbols have the same meanings as described above.
  • the reaction is usually carried out in a solvent.
  • ethers such as tetrahydrofuran (hereinafter referred to as THF), 1,4-dioxane, ethylene glycol dimethyl ether (hereinafter referred to as DME), methyl tert-butyl ether (hereinafter referred to as MTBE)
  • ethers aromatic hydrocarbons such as toluene and xylene
  • aromatic hydrocarbons dimethylformamide (hereinafter referred to as DMF), N-methylpyrrolidone and the like, dimethyl sulfoxide (hereinafter referred to as Aprotic polar solvents (hereinafter referred to as DMSO) and the like (hereinafter referred to as aprotic polar solvents) and mixtures of two or more of these can be mentioned.
  • Examples of the base used for the reaction include organic bases such as triethylamine, diisopyropylethylamine, pyridine and 4-dimethylaminopyridine (hereinafter referred to as organic bases); alkali metal hydrides such as sodium hydride (hereinafter referred to as Alkali metal hydrides); and alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates).
  • organic bases such as triethylamine, diisopyropylethylamine, pyridine and 4-dimethylaminopyridine
  • alkali metal hydrides such as sodium hydride (hereinafter referred to as Alkali metal hydrides)
  • alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates).
  • the compound (R-1) is used in a proportion of usually 1 to 10 mol
  • the base is usually used in a proportion of 1 to
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • the compound of the present invention can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • the compound (R-1) is a commercially available compound or can be produced according to a known method.
  • the compound represented by formula (I-2) (hereinafter referred to as compound (I-2)) is a compound represented by formula (M-2) (hereinafter referred to as compound (M-2)) and the compound represented by formula (R-2) It can be produced by reacting the compound represented by -2) (hereinafter referred to as compound (R-2)) in the presence of a base.
  • X b represents a fluorine atom or a chlorine atom, and the other symbols have the same meanings as described above.
  • the reaction is usually carried out in a solvent.
  • Examples of the solvent used for the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, nitriles and mixtures of two or more of these.
  • Examples of the base used for the reaction include alkali metal hydrides, organic bases and alkali metal carbonates.
  • the compound (R-2) is used in a proportion of usually 1 to 10 mol, and the base is usually used in a proportion of 1 to 5 mol, per 1 mol of the compound (M-2).
  • the reaction temperature is usually in the range of -20 ° C to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • the compound (R-2) is a commercially available compound or can be produced according to a known method.
  • the compound of the present invention can be produced by intramolecular condensation of a compound represented by formula (M-11) (hereinafter referred to as compound (M-11)).
  • compound (M-11) a compound represented by formula (M-11)
  • the symbols have the same meanings as described above.
  • the solvent used for the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, nitriles and mixtures of two or more of these.
  • the reaction can use a condensing agent, an acid, a base or a chlorinating agent.
  • acetic anhydride As a condensing agent, acetic anhydride; trifluoroacetic anhydride; 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as WSC); triphenyl phosphine, base and carbon tetrachloride or tetra odor Mixtures of carbon trioxide and mixtures of triphenyl phosphine and azo diesters such as diethyl azodicarboxylate and the like can be mentioned.
  • the acid include sulfonic acids such as para-toluenesulfonic acid, carboxylic acids such as acetic acid, and polyphosphoric acid.
  • the base examples include organic bases, alkali metal carbonates, alkali metal hydrides, tripotassium phosphate and the like.
  • the chlorinating agent phosphorus oxychloride and the like can be mentioned.
  • the proportion of the condensing agent is usually 1 to 5 mol, and when using an acid, the acid is usually 0.1 mol to 5 mol, relative to 1 mol of the compound (M-11).
  • the base is usually used in a proportion of 1 mol to 5 mol.
  • a chlorinating agent the chlorinating agent is usually used in a proportion of 1 mol to 5 mol.
  • the reaction temperature is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • the compound represented by the formula (I-4) (hereinafter referred to as the compound (I-4)) is a compound represented by the formula (M-2-o) (hereinafter referred to as the compound (M-2-o)) And compound (R-2) in the presence of a base. [Wherein, the symbols have the same meanings as described above. ]
  • the reaction can be carried out according to production method 3.
  • the compound (M-1) is prepared by reacting a compound represented by the formula (M-3) (hereinafter referred to as the compound (M-3)) with bis (pinacolato) diboron in the presence of a base and a metal catalyst. After obtaining the compound represented by (M-4) (hereinafter referred to as compound (M-4)), it can be produced by hydrolyzing compound (M-4). [Wherein, the symbols have the same meanings as described above. ] These reactions can be carried out according to the method described in J. Am. Chem. Soc., 2009, 131, 8855.
  • the compound represented by the compound (M-3-a) (hereinafter referred to as the compound (M-3-a)) is a compound represented by the formula (M-5) (hereinafter referred to as the compound (M-5))
  • it can be produced by oxidizing a compound represented by the formula (M-6) (hereinafter referred to as a compound (M-6)).
  • Compound (M-6) can be produced by oxidizing compound (M-5). [Wherein, the symbols have the same meanings as described above. ] These reactions can be carried out according to production method 1.
  • the compound (M-5) can be produced by reacting a compound represented by the formula (M-7) (hereinafter referred to as compound (M-7)) with ethanethiol in the presence of a base. [Wherein, the symbols have the same meanings as described above. ] The reaction can be carried out according to the method described in WO 2013/018928.
  • Reference manufacturing method 4 Compound (M-7) can be produced by intramolecular condensation of a compound represented by formula (M-8) (hereinafter referred to as compound (M-8)). [Wherein, the symbols have the same meanings as described above. ] The reaction can be carried out according to the method described in WO 2013/018928.
  • the compound (M-8) is a compound represented by the formula (M-9) (hereinafter referred to as compound (M-9)) and a compound represented by the formula (M-10) (hereinafter referred to as the compound (M-10) Can be produced by reacting with [Wherein, the symbols have the same meanings as described above. ] The reaction can be carried out according to the method described in WO 2013/018928.
  • Compound (M-9) and compound (M-10) are commercially available compounds or can be produced according to known methods.
  • the compound (M-1) can be produced by reacting a compound represented by the formula (I-3) (hereinafter referred to as compound (I-3)) in the presence of an acid.
  • a compound represented by the formula (I-3) hereinafter referred to as compound (I-3)
  • the reaction is usually carried out in a solvent.
  • the solvent used for the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, nitriles, water and a mixture of two or more of these.
  • the acid used for the reaction include trifluoroacetic acid, acetic acid and hydrochloric acid.
  • the acid is usually used in a ratio of 1 to 20 moles relative to 1 mole of the compound (I-3).
  • the reaction temperature is usually in the range of -20 ° C to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • water is added to the reaction mixture, extraction is performed with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration to give compound (M-1).
  • Reference manufacturing method 7 Compound (M-11) is produced by reacting compound (M-9) with a compound represented by formula (M-12) (hereinafter referred to as compound (M-12)) in the presence of a condensing agent can do.
  • a condensing agent used for reaction, carbodiimides, such as WSC and a 1, 3- dicyclohexyl carbodiimide, are mentioned, for example.
  • the reaction can also be carried out using a catalyst, if necessary.
  • the catalyst include 1-hydroxybenzotriazole.
  • the catalyst is usually used in a proportion of 0.01 to 1 mole per 1 mole of the compound (M-9).
  • the compound (M-12) is usually used in a proportion of 0.5 to 2 mol and the condensing agent is usually used in a proportion of 1 to 5 mol with respect to 1 mol of the compound (M-9).
  • the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, water is added to the reaction mixture, extraction is performed with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration to give compound (M-11).
  • the compound (M-12) is a compound represented by the formula (M-13) (hereinafter referred to as a compound (M-13)) or a compound represented by the formula (M-18) (hereinafter referred to as a compound (M-18) Can be produced by hydrolysis using an acid or a base.
  • Compound (M-18) can be produced by solvolysis of compound (M-13) with an acid or a base.
  • R 3 represents a methyl group or an ethyl group, and the other symbols have the same meanings as described above.
  • the reaction is usually carried out in an aqueous solution of the acid.
  • mineral acids such as hydrochloric acid, nitric acid, a sulfuric acid, are mentioned, for example.
  • the acid is usually used in a proportion of 1 to 50 moles relative to 1 mole of the compound (M-13).
  • the reaction temperature is usually in the range of 0 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction mixture can be extracted with an organic solvent, and the organic layer can be subjected to post-treatment procedures such as drying and concentration to isolate the compound (M-12).
  • the reaction is usually carried out in a solvent.
  • a solvent used for reaction ether, alcohol, water, and the mixture of 2 or more types of these are mentioned, for example.
  • the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
  • the base is usually used in a proportion of 1 to 10 moles relative to 1 mole of the compound (M-13).
  • the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction mixture is acidified with an acid such as hydrochloric acid, and extracted with an organic solvent, followed by drying and concentration of the organic layer, etc. It can be isolated.
  • the reaction is usually carried out in an aqueous solution of the acid.
  • mineral acids such as hydrochloric acid, nitric acid, a sulfuric acid, are mentioned, for example.
  • the acid is usually used in a proportion of 1 to 50 moles relative to 1 mole of the compound (M-18).
  • the reaction temperature is usually in the range of 0 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction mixture can be extracted with an organic solvent, and the organic layer can be subjected to post-treatment procedures such as drying and concentration to isolate the compound (M-12).
  • the reaction is usually carried out in a solvent.
  • a solvent used for reaction ether, alcohol, water, and the mixture of 2 or more types of these are mentioned, for example.
  • the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
  • the base is usually used in a proportion of 1 to 10 moles relative to 1 mole of the compound (M-18).
  • the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction mixture is acidified with an acid such as hydrochloric acid, and extracted with an organic solvent, followed by drying and concentration of the organic layer, etc. It can be isolated.
  • the reaction is usually carried out in a solvent.
  • the solvent used for the reaction is methanol if R 3 is a methyl group and ethanol if R 3 is an ethyl group.
  • mineral acids such as hydrochloric acid, nitric acid, a sulfuric acid, are mentioned, for example.
  • the acid is usually used in a proportion of 1 to 50 moles relative to 1 mole of the compound (M-13).
  • the reaction temperature is usually in the range of 0 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction mixture can be extracted with an organic solvent, and the organic layer can be subjected to post-treatment procedures such as drying and concentration to isolate the compound (M-18).
  • the reaction is usually carried out in a solvent.
  • the solvent used for the reaction is methanol if R 3 is a methyl group and ethanol if R 3 is an ethyl group.
  • the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
  • the base is usually used in a proportion of 1 to 10 moles relative to 1 mole of the compound (M-13).
  • the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction mixture is acidified with an acid such as hydrochloric acid and extracted with an organic solvent, and the organic layer is dried and concentrated to give a compound (M-18). It can be isolated.
  • the compound represented by the compound (M-13-c) (hereinafter referred to as the compound (M-13-c)) is a compound represented by the formula (M-13-a) (hereinafter referred to as the compound (M-13-a) Or a compound represented by the formula (M-13-b) (hereinafter referred to as a compound (M-13-b)).
  • Compound (M-13-b) can be produced by oxidizing compound (M-13-a). [Wherein, the symbols have the same meanings as described above. ] These reactions can be carried out according to production method 1.
  • the compound (M-13-a) can be produced by reacting a compound represented by the formula (M-14) (hereinafter referred to as compound (M-14)) with a compound (R-2) in the presence of a base It can be manufactured. [Wherein, the symbols have the same meanings as described above. ] The reaction can be carried out according to production method 3.
  • the compound represented by the formula (M-14-a) (hereinafter referred to as a compound (M-14-a)) is a compound represented by the formula (M-15) (hereinafter referred to as a compound (M-15)) And ethanethiol in the presence of a base.
  • the reaction is usually carried out in a solvent.
  • the solvent used for the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents and mixtures of two or more of these.
  • a base used for reaction an alkali metal carbonate and alkali metal hydrides are mentioned, for example.
  • ethanethiol is usually used in a proportion of 1 to 10 mol
  • the base is usually used in a proportion of 1 to 10 mol, per 1 mol of compound (M-15).
  • the reaction temperature is usually in the range of 0 to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • water is added to the reaction mixture, extraction is performed with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration to give compound (M-14-a).
  • Compound (M-15) is a commercially available compound or can be produced according to a known method.
  • Reference manufacturing method 12 Compound (M-14) can be produced by dehydrating a compound represented by formula (M-16) (hereinafter referred to as compound (M-16)). [Wherein, the symbols have the same meanings as described above. ]
  • the reaction is usually carried out in a solvent.
  • the solvent used for the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents and mixtures of two or more of these.
  • the dehydrating agent used for the reaction include thionyl chloride, phosphorus oxychloride and trifluoromethanesulfonic acid.
  • a dehydrating agent is usually used in a proportion of 1 to 10 moles relative to 1 mole of the compound (M-16).
  • the reaction temperature is usually in the range of 0 to 150 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • water is added to the reaction mixture, extraction is performed with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration to give compound (M-14).
  • Compound (M-16) can be produced by reacting a compound represented by formula (M-17) (hereinafter referred to as compound (M-17)) with ethanethiol in the presence of a base.
  • a compound represented by formula (M-17) hereinafter referred to as compound (M-17)
  • X c represents a fluorine atom or a chlorine atom, and the other symbols have the same meanings as described above.
  • the reaction can be carried out according to the method described in Reference Production Method 11.
  • Compound (M-17) is a commercially available compound or can be produced according to a known method.
  • Reference manufacturing method 14 Compound (M-2-o) can be produced by oxidizing compound (M-3-a). [Wherein, the symbols have the same meanings as described above. ] The reaction can be carried out according to the method described in WO 2013/018928.
  • Formula (L-1) Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds Marked as group SX1).
  • a 1 is an oxygen atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a certain compound hereinafter referred to as compound group SX2.
  • a 1 is a sulfur atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a certain compound hereinafter referred to as compound group SX3).
  • a 1 is NCH 3 , A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3]
  • Compound (hereinafter referred to as compound group SX4) In the compound represented by the formula (L-1), A 1 is an oxygen atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a 1 is a sulfur atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX6).
  • Formula (L-2) Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds Marked as group SX7).
  • a 1 is an oxygen atom
  • a 2 is nitrogen atom
  • R2 2 is in one of the substituents described in Table 1] - [Table 3]
  • a certain compound hereinafter referred to as compound group SX8).
  • a 1 is a sulfur atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a certain compound (hereinafter referred to as compound group SX9).
  • a 1 is NCH 3
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • Compound (hereinafter referred to as compound group SX10) In the compound represented by the formula (L-2), A 1 is an oxygen atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a 1 is a sulfur atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX12).
  • Formula (L-3) Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds It describes as group SX13).
  • a 1 is an oxygen atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a certain compound hereinafter referred to as compound group SX14.
  • a 1 is a sulfur atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a certain compound (hereinafter referred to as compound group SX15).
  • a 1 is NCH 3, an A2 2 is CH, R 2 is, is any substituent as defined in Table 1] - [Table 3]
  • a 1 is an oxygen atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a 1 is a sulfur atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • Formula (L-4) Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds It describes as group SX19).
  • a 1 is an oxygen atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a certain compound hereinafter referred to as compound group SX20.
  • a 1 is a sulfur atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a certain compound (hereinafter referred to as compound group SX21).
  • a 1 is NCH 3 , A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a 1 is an oxygen atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a 1 is a sulfur atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • Formula (L-5) Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds Marked as group SX 25).
  • a 1 is an oxygen atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a certain compound hereinafter referred to as compound group SX26).
  • a 1 is a sulfur atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a certain compound hereinafter referred to as compound group SX27
  • a 1 is NCH 3
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a 1 is an oxygen atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a 1 is a sulfur atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • Formula (L-6) Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds It describes as group SX31).
  • a 1 is an oxygen atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a certain compound hereinafter referred to as compound group SX32).
  • a 1 is a sulfur atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a certain compound hereinafter referred to as compound group SX33
  • a 1 is NCH 3
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a 1 is an oxygen atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a 1 is a sulfur atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • Formula (L-9) Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds Marked as group SX39).
  • a 1 is an oxygen atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a certain compound hereinafter referred to as compound group SX40).
  • a 1 is a sulfur atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a certain compound hereinafter referred to as compound group SX41
  • a 1 is NCH 3
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a 1 is an oxygen atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a 1 is a sulfur atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • Formula (L-10) Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds It describes as group SX45).
  • a 1 is an oxygen atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a certain compound hereinafter referred to as compound group SX46).
  • a 1 is a sulfur atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a certain compound hereinafter referred to as compound group SX47.
  • a 1 is NCH 3
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a 1 is an oxygen atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • A1 1 is a sulfur atom
  • an A 2 is CH
  • R 2 is, is any substituent as defined in Table 1] - [Table 3]
  • Compound hereinafter, referred to as compound group SX50).
  • Formula (L-11) Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds It describes as group SX51).
  • a 1 is an oxygen atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a certain compound hereinafter referred to as compound group SX52).
  • a 1 is a sulfur atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a certain compound hereinafter referred to as compound group SX53.
  • a 1 is NCH 3
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a 1 is an oxygen atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a 1 is a sulfur atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • Formula (L-12) Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds It describes as group SX57).
  • a 1 is an oxygen atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a certain compound hereinafter referred to as compound group SX58).
  • a 1 is a sulfur atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a certain compound hereinafter referred to as compound group SX59
  • a 1 is NCH 3
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • Compound hereinafter referred to as compound group SX60
  • a 1 is an oxygen atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a 1 is a sulfur atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • Formula (L-13) Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds Marked as group SX63).
  • a 1 is an oxygen atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a certain compound hereinafter referred to as compound group SX64).
  • a 1 is a sulfur atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a certain compound hereinafter referred to as compound group SX65
  • a 1 is NCH 3
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a 1 is an oxygen atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a 1 is a sulfur atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • Formula (L-14) Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds Marked as group SX69).
  • a 1 is an oxygen atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a certain compound hereinafter referred to as compound group SX70).
  • a 1 is a sulfur atom
  • a 2 is a nitrogen atom
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a certain compound hereinafter referred to as compound group SX71
  • a 1 is NCH 3
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • a 1 is an oxygen atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3].
  • a 1 is a sulfur atom
  • a 2 is CH
  • R 2 is any of the substituents described in [Table 1] to [Table 3]
  • Formula (L-15) In the compound represented by the formula, R y is a cyano group, n is 0, and R 2 is any of the substituents described in [Table 1] to [Table 3]. In the compound represented by the formula (L-15), compounds wherein R y is a cyano group, n is 1 and R 2 is any of the substituents described in [Table 1] to [Table 3] . In the compound represented by the formula (L-15), compounds wherein R y is a cyano group, n is 2 and R 2 is any of the substituents described in [Table 1] to [Table 3] .
  • R y is a methoxycarbonyl group, n is 0, and R 2 is any of the substituents described in [Table 1] to [Table 3].
  • R y is a methoxycarbonyl group, n is 1 and R 2 is any of the substituents described in [Table 1] to [Table 3]
  • R y is a methoxycarbonyl group, n is 2 and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound.
  • R y is an ethoxycarbonyl group, n is 0, and R 2 is any of the substituents described in [Table 1] to [Table 3].
  • R y is an ethoxycarbonyl group, n is 1 and R 2 is any of the substituents described in [Table 1] to [Table 3].
  • R y is an ethoxycarbonyl group, n is 2 and R 2 is any of the substituents described in [Table 1] to [Table 3].
  • Formula (L-16) In the compound shown by this, a compound in which R y is a cyano group, n is 0, and R 2 is a fluorine atom or a chlorine atom.
  • R y In the compound represented by the formula (L-16), compounds wherein R y is a cyano group, n is 1 and R 2 is a fluorine atom or a chlorine atom.
  • the compounds of the present invention are selected from the group consisting of the following groups (a), (b), (c), (d), (e), (f), (g) and (h): Can be used together or in combination with one or more components (hereinafter referred to as "the component").
  • the above-mentioned combined use or combined use means using the compound of the present invention and the present component simultaneously, separately or at time intervals.
  • the compound of the present invention and the component may be contained in separate formulations or may be contained in one formulation.
  • One aspect of the present invention is one or more components selected from the group consisting of group (a) and group (b), and a composition containing the compound of the present invention (hereinafter referred to as “composition A”) .
  • Group (a) includes acetylcholinesterase inhibitors (eg carbamate insecticides, organophosphorus insecticides), GABAergic chloride ion channel antagonists (eg phenylpyrazole insecticides), sodium channel modulators (eg pyrethroid insecticides) Nicotinic acetylcholine receptor antagonistic modulators (eg, neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamatergic chloride ion channel allosteric modulators (eg, macrolide insecticides), juvenile hormone mimic , Multi-site inhibitor, chordal organ TRPV channel modulator, mite growth inhibitor, mitochondrial ATP biosynthesis enzyme inhibitor, oxidative phosphorylation uncoupling agent, nicotinic acetylcholine receptor Channel blockers (eg, nereistoxin insecticides), chitin synthesis inhibitors, molting inhibitors, ecdysone receptor
  • Group (b) includes nucleic acid synthesis inhibitors (eg, phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeleton inhibitors (eg, MBC fungicides), respiratory inhibitors (eg, QoI fungicides) , Qil fungicides), amino acid synthesis and protein synthesis inhibitors (eg, anilinopyridine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (eg, triazole etc.
  • nucleic acid synthesis inhibitors eg, phenylamide fungicides, acyl amino acid fungicides
  • cell division and cytoskeleton inhibitors eg, MBC fungicides
  • respiratory inhibitors eg, QoI fungicides
  • Qil fungicides Qil fungicides
  • amino acid synthesis and protein synthesis inhibitors eg, anilinopyridine fungicides
  • DMI DMI
  • bactericidal agents cell wall synthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-active point contact active disinfectants, active ingredients of microbial disinfectants, and other bactericidal active ingredients. These are described in the classification based on the mechanism of action of FRAC.
  • Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).
  • Group (d) is a group of safeners.
  • Group (e) is a group of synergists.
  • Group (f) is a group of repellent components consisting of a bird repellent component, an insect repellent component and an animal repellent component.
  • Group (g) is a group of mollusc components.
  • Group (h) is a group of insect pheromone.
  • alanicarb (Salyx + SX) means a combination of alanicarb (Salyx).
  • SX means any one compound of the present invention selected from the compound groups SX1 to SX74.
  • all of the components described below are known components and can be obtained from commercially available preparations or can be produced by known methods.
  • the component is a microorganism, it can also be obtained from a bacteria depository.
  • the numbers in parentheses indicate CAS RN (registered trademark).
  • a combination of the present component of the above group (a) with the compound of the present invention Abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acririnathrin + SX, acynonapyr + SX, afidopyropene + SX, afoxolaneal (Afoxolaner) + SX, alaniccarb (alanycarb) + SX, aldicarb (aldicarb) + SX, allethrin + SX, alpha-cypermethrin (alpha-cypermethrin) + SX, alpha-endosulfan (alpha-endosulfan) + SX, phosphorylated Aluminum (phosphide) + SX, amitraz (Amitraz) + SX, azadirachtin + SX, azamethiphos (Azamethiphos) + SX, azin
  • pomonella granulosa virus V15 (Cydia pomonella GV V 15) + SX, S. s. Pomonella granule disease virus V22 (Cydia pomonella GV V22) + SX, Cryptofrebbia leukotleta granule disease virus (Cryptophlebia leucotreta GV) + SX, Dendolimus punctatus cytoplasmic polyhedron virus (Dendrolimus punctatus cypovirus) + SX, Helicoverpa armigera nucleus polygonia Body disease virus BV-0003 strain (Helicoverpa armigera NPV BV-0003) + SX, Helicoverpa zea nuclear polyhedrosis virus (Helicoverpa zea NPV) + SX, Lymantria dispar nuclear polyhedrosis virus (Lymantria dispar NPV) + SX, Mamestra ⁇ Brassicae nuclear polyhedrosis virus (Mam
  • Strain AQ175 (Bacillus sp. AQ175) + SX, Bacillus sp. Strain AQ 177 (Bacillus sp. AQ 177) + SX, Bacillus sp. Strain AQ 178 (Bacillus sp.
  • Bacillus sphaericus 2362 Bacillus sphaericus 2362 + SX, Bacillus sphaericus ABTS 1743 (Bacillus sphaericus ABTS 1743) + SX, Bacillus sphaericus Serotype H 5a 5 b (Bacillus sphaericus Serotype H 5 a 5 b) + SX, Bacillus thuringiensis AQ 52 strain (Bacillus thuringiensis AQ 52) + SX, Thuringiensis strain BD # 32 (Bacillus thuringiensis BD # 32) + SX, Bacillus thuringiensis strain CR-371 (Bacillus thuringiensis CR-371) + SX, Bacillus thuringiensis.
  • EG7841 strain Bacillus thuringiensis subsp. Kurstaki EG7841 +) SX, Bacillus thuringiensis cristaea subsp. EVB 113-19 (Bacillus thuringiensis subsp. Kurstaki EVB 113-19) + SX, Bacillus thuringiensis cristae subsp. F 810 (Bacillus thuringiensis subsp. Kurstaki F 810) + SX, Bacillus thuringiensis cristaea subsp. HD-1 strain (Bacillus thuringiensis subsp. Kurstaki HD-1) + SX, Bacillus thuringiensis cristae subsp.
  • Strain PB54 Bacillus thuringiensis subsp. Kurstaki PB54 + SX, Bacillus thuringiensis ⁇ Christeraki subspecies strain SA-11 (Bacillus thuringiensis subsp. Kurstaki SA-11) + SX, Bacillus thuringiensis ⁇ Christase strain subspecies SA-12 (Bacillus thuringiensis subsp. Kurstaki SA-12) + SX, Bacillus thuringiensis ⁇ B. thuringiensis subsp. Strain NB176 (Bacillus thuringiensis subsp. Tenebriosis NB176) + SX, Bacillus thuringiensis ⁇ Chu Ringing cis subsp.
  • Strain MPPL 002 Bacillus thuringiensis subsp. Thuringiensis MPPL 002 + SX, Bacillus thuringiensis subsp. Morrisoni subsp. Strain (Bacillus thuringiensis subsp. Morrisoni) + SX, Bacillus thuringiensis col. SX, Bacillus thuringiensis dermstasis variant 24-91 (Bacillus thuringiensis var. Darmstadiensis 24-91) + SX, Bacillus thuringiensis dendolimus variant (Bacillus thuringiensis var.
  • SX Bacillus thuringiensis San Diego variant M-7 strain (Bacillus thuringiensis var. san diego M-7) + SX, Bacillus thuringiensis-7216 variant (Bacillus thuringiensis var. 7216) + SX, Bacillus thuringiensis-aegypti variant (Bacillus thuringiensis var.
  • Aegypti + SX, Bacillus thuringiensis-T36 variant (Bacillus thuringiensis var) .T36) + SX, Beauberia basiana ANT-03 strain (Beauvelia bassiana ANT-03) + SX, Beauberia basiana strain ATCC 74040 (Beauvelia bassiana ATCC 74040) + SX, Beauberia basiana strain GHA (Beauvelia bassiana GHA) + SX, bovelia ⁇ Bronniati (Beauveria brongniartii) + SX, Burkholderia capitansis A 396 strain (Burkholderia rinojensis A 396) + SX, Chromobacteria suborbitum PRAA4-1T strain (Chromobacterium subtsugae PRAA4-1T) + SX, Dactylella ellipsospora + SX, Dectylaria thaumasia + SX, Hilster
  • pelyomyces tenuipes T1 strain (Paecilomyces tenuipes T1) + SX ⁇ Nishizawae Pn1 strain (Pasteuria nishizawae Pn1) + SX, Pasteuria penetrans (Pasteuria penetrans) + SX, Pasteuria usgae (Pasteuria usgae) + SX, Pasteuria toynei (Pasteuria thoynei) + SX, Serratia entomophila + SX, Verticillium chlamydosporium (Verticillium chlamydosporium) + SX, Verticillium lecani strain NCIM 1312 (Verticillium lecani NCIM 1312) + SX.
  • a combination of the present component of the above group (b) with the compound of the present invention Acibenzolar S methyl (acibenzolar-S-methyl) + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, amisulblom + SX, anilazine + SX, Azaconazole + SX, azoxystrobin + SX, basic copper sulfate + SX, benalaxyl + SX, benalaxyl M (benalaxyl-M) + SX, benodanil + SX, benomyl + SX, benchiavalicarab (benthiavalica b) + SX, bench avalia carib isopropyl (benthivalicarb-isopropyl) + SX, benzobin diflupyr (benzovidiflupyr) + SX, binapacryl (Spa, bax) Biphenyl (bipheny
  • Amyloliquefaciens B3 strain (Bacillus amyloliquefaciens B3) + SX, Bacillus amyloliquefaciens strain D747 (Bacillus amyloliquefaciens D747) + SX, Bacillus amyloliquefaciens strain DB101 (bacillus amyloliquefaciens DB101) + SX, Bacillus amyloliquefaciens DB101 Faciens DB102 strain (Bacillus amyloliquefaciens DB102) + SX, Bacillus amyloliquefaciens GB03 strain (Bacillus amyloliquefaciens GB03) + SX, Bacillus amyloliquefaciens FZB24 strain (Bacillus amyloliquefaciens FZB24) + SX, Bacillus amyloliquefaciens FZB42 strain (Bacillus amylolique
  • subtilis HAI 0404 strain Bacillus subtilis HAI 0404 strain (Bacillus subtilis HAI 0404) + SX, Bacillus subtilis IAB / BS03 strain (Bacillus subtilis IAB / BS03) + SX, Bacillus subtilis MBI 600 strain (Bacillus subtilis MBI 600) + SX, Bacillus subtilis QST 30002 / AQ 30002 ( Bacillus subtilis QST30002 / AQ30002) + SX, Bacillus subtilis QST30004 / AQ30004 (Bacillus subtilis QST30004 / AQ30004) + SX, Bacillus subtilis Sus QST 713 (Bacillus subtilis QST 713) + SX, Bacillus subtilis QST 714 (Bacillus subtilis QST 714) + SX, Bacillus subtilis var.
  • CAB-02 strain (Pseudomonas sp. Strain (Pseudomonas syringae 742 RS) + SX, Pseudomonas syringae MA-4 strain (Pseudomonas syringae MA-4) + SX, Pseudozyma flocculosa PF-A22UL strain (Pseudozyma flocculosa PF-A22UL) + SX, Pseudomonas rhodesia HAI-804 strain (Pseudomonas rhodesiae HAI-0804) + SX, Pythium oligand Rum DV 74 strain (Pythium oligodrum DV 74) + SX, Streptomyces griseoviridis K 61 strain (Streptomyces griseoviridis K 61) + SX, Streptomyces lydicus WY
  • a combination of the present component of the above group (c) with the compound of the present invention 1-methylcyclopropene (1-methylcyclopropene) + SX, 2,3,5-triiodobenzoic acid (2, 3,5- triiodobenzoic acid) + SX, IAA ((1H-indol-3-yl) acetic acid ((1H) -indol-3-yl) acetic acid)) + SX, IBA (4- (1H-indol-3-yl) butyric acid ((4- (1H-indol-3-yl) butyric acid)) + SX, MCPA ( 2- (4-chloro-2-methylphenoxy) acetic acid (2- (4-chloro-2-methylphenoxy) acetic acid) + SX, MCPB (4- (4-chloro-2-methylphenoxy) acetic acid (4- (4-chloro-2-methylphenoxy) acetic acid) (4-chloro-2-methylphenoxy)
  • Claroideum (Claroideoglomus claroideum) + SX, Delphithia Acidoboranes RAY 209 (Delftia acidovorans RAY 209) + SX, Gigaspora margarita (Gigaspora margarita) + SX, Gigaspora rosea (Sig) + SX, Glmus de Cellicolac SX, Glomus monosporum + SX, Mesorhizobium ciceri + SX, Mesorhizobium huakii + SX, Rhizophagus clarus + SX, Rhizobium + Rhizobium et al. SX, Rhizobium galegae + SX, Rhizophagus ieglalis DAOM 19719 (Rhizophagus irregularis DAOM 197198) + SX, Paraglomus brasillianum + SX.
  • the ratio of the compound of the present invention to the component is not particularly limited, but the weight ratio (the compound of the present invention: this component) is 1,000: 1 to 1: 1,000, 500: 1 to 1: 500. 100: 1 to 1: 100, 50: 1 to 1:50, 20: 1 to 1:20, 10: 1 to 1:10, 3: 1 to 1: 3, 1: 1 to 1: 500, 1 And the like: 1: 1 to 1: 100, 1: 1 to 1:50, 1: 1 to 1:20, 1: 1 to 1:10, and the like.
  • the compounds of the present invention are effective against harmful arthropods such as harmful insects, harmful mites, harmful nematodes and harmful molluscs.
  • harmful arthropods include, but are not limited to:
  • Hemiptera Hemetobiunka (Laodelphax striatellus), Tobiirounka (Nilaparvata lugens), Sejirounka (Sogatella furcifera), Maize (Peregrinus maidis), Lobluntia (Javesella pellucida), Black-tailed Uchiluciculicus Leafhopper family (Delphacidae); green leafhopper (Nephotettix cincticeps), giant leafhopper green leafhopper (Nephotettix virescens), black leafhopper green leafhopper (Nephotettix nigropictus), green leafhopper leafworm (Recilia dorsalis), green leafhopper foliage ), Corn leaf hopper (Dalbulus maidis), white leafhopper (Cofana spectra), etc.
  • Helicidae (Coreidae); hemipterus), a Red-headed Bug family (Lygaeidae), such as Blissus leucopterus; Red-backed squirrels (Trigonotylus caelestialium), Red-backed snails (Stenotus rubrovittatus), Scutellaris moth (Stenotema calcarata), Myrtleidae (Miridae); Onion's Beak (Trialeurodes vaporariorum), B. tabaci (Bemisia tabaci), I.
  • Whitefly (Aleyrodidae); White-backed scale insect (Abgrallapsis cyanophylli), Red-backed scale insect (Aonidiella aurantii), Nasi-maroon scaleworm (Diaspidiotus perniciosus), Musk Red-tailed beetles (Diaspididae), such as ruminants (Pseudaulacaspis pentagona), Red-winged beetles (Unaspis yanonensis), False-tailed scaled insects (Unaspis citri), etc .; Parchacia, Icarya seychellarum et al. (Margarodidae); P.
  • Triatoma spp. Such as the semi-family (Cicadidae) such as Giant Cicada (Quesada gigas) and the Brazilian red-handed turtle (Triatoma infestans).
  • Lepidoptera insects Lepidoptera: Nymphs (Chilo suppressalis), Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Itten's tree magnolia (Scirpophaga incertulas), Rupela albina, Kobomeiga (Cinatalitraceitraceitracel Red clover (Marasmia exigua), cotton dwarf (Notarcha derogata), African dwarf (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), black-legged moth (Hellula undulis), Monquil chronogare (Herpetogramma luctiguete) Rice case worms (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), etc.
  • Arctiidae Giant Sugarc Anemoneidae (Castniidae) such as Ane borer (Telchin licus); Bacteriidae (Cossidae) such as Cossus insularis etc .; Anemone family (Limacodidae); Anemoneidae (Stathmopoda niessa), such as Stathmopodidae; Acherontia lachesis, such as Sphingidae (Sphingidae); Tenuis) et al.
  • insects of the rice tortoise (Parnara guttata) et al., Hesperiidae, pests of the family Iridaceae (Tinedae) such as the liga (Tinea translucens), and the lichen (Tineola bisselliella).
  • Thysanoptera Thripsidae (Frankliniella occidentalis), Thrips palmi (Thrips palmi), Chalyss occidentalis (Scirtothrips dorsalis), Locustoids (Thrips tabaci), Philosophis japonicus (Frankliniella intimasite) ), Thripidae such as Echinothrips americanus etc .; Pests of the Thripsidae (Phlaeothripidae) such as Haekohrips aculeatus.
  • Insect pests of the order Diptera (Diptera): Seed fly (Delia platura), onion fly (Delia antiqua), sugar beet fly (Pegomya cunicularia), etc. (Anthomyiidae); Sugar beet root maggot (Tetanops myopaeformis) etc.
  • Agrobacterium family (Agromyza oryzae), a tomato leafhopper (Liriomyza sativae), a rice leafminer fly (Liriomyza trifolii), a leafminer fly (Chromatomya horticola), and the like (Agromyzidae); (Bactrocera cucurbitae), Citrus fruit fly (Bactrocera dorsalis), Nassy fruit fly (Bactrocera latiphrons), Olive fruit fly (Bactrocera oleae), Quinceland fruit fly (Bactrocera tryoni), Citrus fruit fly (Ceratitis capitata) Tephritidae (Tephritidae), such as letis pomonella, sweet potato fruit fly (Rhacochlaena japonica), etc .; Ephydridae); Drosophila (Drosophila suzukii) etc .; Drosophila family (Drosophilidae); Brachysia
  • Coleoptera insect pest (Coleoptera): Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi), Northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), Banded Cucumber Beetle (Diabrotica virgifera zeae) Culibita beetle (Diabrotica balteata), Cucurbit Beetle (Diabrotica speciosa), Bean leaf beetle (Cerotoma trifurcata), Kubi ⁇ ⁇ ⁇ ⁇ (Oulema melanopus), ground leaf beetle (Aulacophora femoralis), ⁇ ⁇ ⁇ ⁇ ⁇ Phylloteta striolate ⁇ tle ( black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylli
  • Phyllophaga such as Haga crinita, Scarabaeidae (Scarabaeidae) such as Diloboderus (Diloboderus spp.) such as Diloboderus abderus; Euscepes postfasciatus), alfalfate weevil (Hypera postica), tree weevil (Sitophilus zeamais), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), Shirosuio sage beetle (Rhabdoscelus lineate history) Sphenophorus venatus), Southern Corn Billbug (Sphenophorus callosus), Soybean stalk weevil (Sternechus subsignatus), Sugarcane weevil (Sphenophorus levis), Crustacean weevil (Scepticus griseus), Tobiiro gourd (Sc
  • Tricholium castaneum Tricholium confusum (Tenebrionidae) such as Tricholium castaneum, Tribolium conducum (Tenebrionidae); Etirachnida (Coccinellidae) such as Epilachna vigintopoc unctata, etc .
  • Family Bostodian
  • Streptomyces Ptinidae
  • Anemone longhorn Anoplophora malasiaca
  • Orthopteran pests Orthoptera: Toocta grasshoppers (Locusta migratoria), Toroca grasshoppers (Dociostaurus maroccanus), Australian Tobetta grass (Chortoicetes terminifera), Red-footed grasshoppers (Nomadacris septemfasciata), Brown Locust (Locustana palligates) Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipelus), Red-Legged grasshopper (Melh gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Kobayinago (Oxya yezoensis), Hanekinainago (Oxya japonica), Trichoderma japonicus (
  • Hymenoptera pests Japanese gossips (Athalia rosae), Japanese black-billed wasps (Athalia japonica), etc. (Tenthredinidae); Brown leaf-cutting ant (Atta capiguara), etc., Atta spp., Acromyrmex spp., Paraponera clavata, Rucheli (Ochetellus glaber), Houseworm (Monomorium pharaonis), Argentine Ali (Linepithema) humile), black rock ants (Formica fusca japonica), short-necked ants (Pheidole noda), horned ants (Pheidole megacephala), black-necked ants (Camponotus japonicus), red-winged great ants (Camponotus obculipes), etc.
  • Ali (Pogonomyrmex occidentalis) etc Anemone family (Pagonomyrmex), an earthworm (Wasmania auropunctata), etc., a genus of earthworm (Wasmania), a family of an ant family (Formicidae) such as a green leaf ant (Anoplolepis gracilipes), a giant hornbill (Vespa manadinia japonica), an anemone carp Vespha anilis Fabriciusi, Vespa velutina, Polistes jokahamae, etc., Hornetidae (Vespidae), Momin's giant bee (Urocerus gigas) etc. Psyllididae (Siricidae), Arigatidae pests
  • Cockroach second order German cockroach (Blattella germanica) and other German cockroaches (Blattellidae); Family (Blattidae); Yamato termites (Reticulitermes speratus), German termites (Coptotermes formosanus), American termites (Incisitermes minor), Dixtermite termites (Cryptotermes domesticus), Tiwanite termites (Odontotermes formosanus), Origami termites (Glyptotermes satsumensis), Phytotermite (Glyptotermes nakajimai), Catan termite (Glyptotermes fuscus), Giant termite (Hodotermopsis sjostedti), Phytotermite (Coptotermes guangzhouen) sis), Amabi termite (Reticulitermes amamianus), Mamitake termite (Reticulitermes miyatakei), Cammon termite (
  • Flea order pest (Siphonaptera): cat flea (Ctenocephalidae felis), dog flea (Ctenocephalides canis), cypress flea (Pulex irritans), pheasant flyfish (Xenopsylla cheopis), sunaw tree (Tunga penetrans), chick flea (Echidnophaga gallinacea) Pests such as mouse fleas (Nosopsyllus fasciatus).
  • Pests Lice pig lice (Haematopinus suis), lice (Haematopinus eurysternus), sheep lice (Dalmalinia ovis), lice (Linognathus seypsus), lice lice (Pediculus humanis), body lice (Pediculucus humanus corporis) , Pests such as white-tailed lice (Phthirus pubis).
  • Psyllid pests (Mallophagida): Bovine flea (Dalmalinia bovis), sheep flea (Dalmalinia ovis) etc. Bovicola sp. (Bovicola spp.); Et al. (Felocpla spp), chicken long-tailed lice (Lipeurus caponis) etc. Peurus (Lipeurus spp.), Trimenopon sp. (Trimenopon spp), Menopon spp. Etc. pests of the family Tricholaridae (Menoponidae) .
  • Acarid pests (Acari): Two-spotted spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai), Mitosuban spider mite (Tetranychus evansi), Citrus red spider mite (Panonychus citri), apple spider mite (Panonychus ulmi), genus Oligonikus (Oligonychus spp.) Citrus mite (Aculops pelekassi), Citrus snail (Phyllocoptruta citri), Tomato snail (Aculops lycopersici), Scutellaris mite (Calacarus carinatus), Scutellariad mite (Acaphylla theavagrans), Nigella vulgaris (Acarus convincedendali), Aceria diospyri, Aceria tosichella, Eriophyidae such as Shevtchenkella sp .; Eriophyidae; Polyphagotarsonemus
  • Red-handed spider mite such as tick (Brevipalpus phoenicis); Teratididae (Tuckerelidae); ⁇ Andersoni (Dermacentor and ersoni), Ixodes ovatus, Ixodes persulcatus, Ixodes ricinus, Black legged tick (Ixodes scapularis), American brown mite (Amblyomma americanum), Ambrium platinum rim maculatum), Boophilus microplus, Boophilus annulatus, Rhipicephalus sanguineus, and other ticks (Ixodidae); Acaridae (Acaridae), such as spiny pokeweed (Tyrophagus similis); Dermatophagoides farinae, Dermatophagoides pteronyssinus, etc .; Dermatophagiaceae (Pyroglyphidae); Red-handed mite (Chyletidae), such as the red-handed spider mite (Tenuipal
  • Arachnid pests Pests of the family Eidichuridae, such as Chehiracanthium japonicum; and pests of the family Theridiidae, such as Latrodectus hasseltii.
  • Ovisyasdes pest Plantsmida: Pests of the family Azalea (Paradoxosomatidae), such as yellow-faced snail (Oxidus gracilis), yellow-tailed snail (Nedyopus tambanus).
  • Isopoda pests pests of the Scutellariadidae family (Armadillidiidae), such as Armadillium vulgare.
  • Lipopod pests (Chilopoda): Scutigeridae such as Thereuonema hilgendorfi; Scolopendra subspinipes et al. (Scolopendridae); .
  • Gastropoda pests Limax marginatus, Limax flavus, etc. (Limacidae); Ligacidae, such as slugs (Meghimatium bilineatum); Et al. (Ampullariidae); Pests of the family Monacaridae (Lymnaeidae) such as Aestropeplea ollula.
  • Nematoda Aphelenchoides spp. (Aphelenchoides bessei) etc. Aphelenchoididae (Aphelenchoididae); similis) and the like (Pratylenchidae); Javanese Nematode (Meloidogyne javanica), Sweet potato Nematode (Meloidogyne incognita), Northern Nervosa (Meloidogyne hapla), Soybean cyst nematode (Heterodera glycines), White-tailed nematode (Globodera pallida) heterodera (Heteroderidae); Rotylenchulus reniformis et al.
  • the harmful insects and harmful mites may be insects and acarids that have reduced drug sensitivity to insecticidal and acaricidal agents, or have developed drug resistance.
  • the drug sensitivity is significantly reduced or drug resistance is significantly developed, it is desirable to use the composition of the present invention containing an insecticidal and acaricidal component other than the target insecticidal and acaricidal agent.
  • the compounds of the present invention can also be used to protect plants from plant diseases caused by insect-borne viruses or insect-borne bacteria.
  • Such insect-borne viruses include, for example, the following.
  • Rice hatching virus (Rice tungro spherical virus), rice tungro bacillus virus (Rice tungro bacilliform virus), rice grassy stunt virus (Rice grassy stunt virus), rice ragged stunt virus (Rice ragged stunt virus), rice streak dead virus ( Rice stripe virus), Rice black streaked dwarf virus, Rice southern black streaked dwarf virus, Rice gall dwarf virus, Rice hoja disease (Rice hoja) blanca virus), rice yellow leaf virus (Rice yellow stunt virus), rice yellow mottle virus, rice dwarf virus, wheat cereals northern virus (Northern cereal mosaic virus) barley yellow dwarf virus (Barley yellow dwarf virus), Barley mild mosaic virus, Barley yellow dwarf virus (Barley yellow dwarf virus-PAV), Ruiki ⁇ RPS virus (Cereal yellow dwarf virus-RPS), wheat yellow leaves virus (Wheat yellow leaf virus), Oat sterile dwarf virus, Wheat streak mosaic virus, Maize dwarf mosaic virus (Maize dwarf mosaic virus), Maize stripe virus, Maize chlorotic mottle virus, Maize chlorotic dwarf virus, Maize ray
  • insect-borne bacteria examples include the following.
  • Rice yellow dwarf phytoplasma (Candidatus Phytoplasma oryzae), Candidatus Phytoplasma asteris, Maize bushy stunt phytoplasma, citrus greening fungus Asian type (Candidatus Liberbacter asiaticus), citrus greening fungus African type (Candidatus Liberbacter aflicanus), Type (Candidatus Liberbacter americanus) etc.
  • the noxious arthropod controlling composition of the present invention contains the present compound or composition A and an inert carrier (hereinafter referred to as "the present composition").
  • the composition of the present invention generally mixes the compound or composition A of the present invention with an inert carrier such as a solid carrier, liquid carrier, gaseous carrier, and, if necessary, a surfactant and other adjuvants for formulation.
  • an inert carrier such as a solid carrier, liquid carrier, gaseous carrier, and, if necessary, a surfactant and other adjuvants for formulation.
  • solid carriers used in formulation include clays (kaolin clay, diatomaceous earth, bentonite, fuvasami clay, acid clay etc.), dry silica, wet silica, talc, ceramic, and other inorganic minerals (sericite, quartz, Fine powders and particles such as sulfur, activated carbon, calcium carbonate etc., chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, sodium chloride etc.) and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate) And polyester resins, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymers, and the like.
  • clays kaolin clay, diatomaceous earth, bentonite, fuvasami clay, acid clay etc.
  • dry silica wet silica,
  • liquid carriers examples include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone etc.), aromatic hydrocarbons (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc., nitriles (ace
  • Gaseous carriers include, for example, fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide gas.
  • surfactants examples include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactants may be mentioned.
  • fixing agents As other pharmaceutical adjuvants, fixing agents, dispersing agents, coloring agents, stabilizers and the like, specifically, for example, casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, 2,6-di-tert-butyl-4-methylphenol, BHA (2-tert-butyl-4-methoxyphenol) And a mixture of 3-tert-butyl-4-methoxyphenol).
  • saccharides starch, gum arabic, cellulose derivatives, alginic acid etc.
  • lignin derivatives bentonite
  • Synthetic water-soluble polymers polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.
  • isopropyl acid phosphate 2,6
  • Examples of the base material of the resin preparation include vinyl chloride polymers, polyurethane and the like, and phthalate esters (dimethyl phthalate, dioctyl phthalate, etc.), adipates, etc. may be used as necessary for these bases. And a plasticizer such as stearic acid may be added.
  • the resin formulation is obtained by kneading the compound in the base using a common kneading apparatus, and then molding by injection molding, extrusion molding, press molding and the like, and if necessary, through further steps such as molding and cutting, It can be processed into resin preparations such as plate-like, film-like, tape-like, net-like and string-like.
  • These resin preparations are processed, for example, as animal collars, animal ear tags, sheet preparations, drawstrings, horticultural posts.
  • the substrate for poison bait include cereal flour, vegetable oil, sugar, crystalline cellulose and the like, and further, if necessary, preservation of antioxidant such as dibutyl hydroxytoluene, nordihydroguaiaretic acid, dehydroacetic acid etc. ,
  • An anti-mistake agent for children and pets such as capsicum powder, a cheese flavor, an onion flavor and a pest-inducing flavor such as peanut oil are added.
  • an effective amount of the composition of the present invention is directly applied to the arthropod pest and / or to a habitat of the arthropod pest (plant, soil, house, animal, etc.) It is carried out by applying. It can also be treated on seeds.
  • plants include whole plants, stems and leaves, flowers, ears, fruits, trunks, branches, crowns, seeds, vegetative organs and seedlings.
  • the vegetative organ means the plant roots, stems, leaves, etc. that have the ability to grow when the site is separated from the main body and installed in the soil.
  • the vegetative reproductive organs for example, tuberous root, creeping root, bulb, corm or solid bulb, tuber, tuber, rhizome, stolon Rhizophores, cane cuttings, propagule and vine cutting.
  • a toothpick is also called a runner (runner), and a basket is also called a sprout and is divided into a broad bud and a bulbil (bulbil).
  • “Vine” means shoots such as sweet potato and yam (collectively referred to as leaves and stems, shoot).
  • bulbs corms, tubers, rhizomes, stem fragments, rhizomes or tuberous roots are collectively referred to as bulbs.
  • cultivation of potato starts by planting tubers in the soil, but the tubers used are generally called seed potatoes.
  • Examples of the method of applying the composition of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, smoke treatment, water surface treatment and seed treatment.
  • a method of applying an effective amount of the composition of the present invention to a plant or a soil for cultivating a plant for example, a method of applying an effective amount of the compound of the present invention or the composition of the present invention to plants
  • a method of applying an effective amount of the compound of the present invention or the composition of the present invention to plants A method of applying an effective amount of the compound of the present invention or the composition of the present invention to seeds or vegetative reproductive organs such as coats, and an effective amount of the compound of the present invention or the composition of the present invention in the soil before planting or after planting Methods of applying
  • a method for controlling harmful arthropods by applying an effective amount of the composition of the present invention to the soil before planting or after planting is, for example, protection from damage such as feeding by harmful arthropods
  • planting hole processing planting hole spraying, planting hole treated soil mixing
  • stock source treatment stock source spraying, stock source soil mixing, stock source irrigation, rearing seedling period second half stock source processing
  • weeding groove Treatment plant groove dispersion, mixture groove soil mixing
  • line processing line distribution, line soil mixing, growth period line dispersion
  • sowing processing at the time of sowing line dispersion at the time of sowing, soil mixing at the time of sowing
  • All-surface treatment all-surface soil spraying, all-surface soil mixing
  • side treatment water surface treatment
  • water surface application spring application after water application, water surface application
  • other soil dispersion treatment growing season foliage surface dispersion, under crown or around main trunk
  • the application rate is usually 1 to 10,000 g of the present compound per 10,000 m 2 .
  • the effective amount of the compound of the present invention is usually 0.001 to 100 g, preferably 0.02 to 20 g, per kg of the seed or vegetative organ.
  • the effective amount of the composition A is usually 0.001 to 100 g, preferably 0.01 to 50 g, per kg of the seed or vegetative organ.
  • the composition of the present invention is formulated into an emulsion, a wettable powder, a flowable, etc., it is usually diluted with water so as to have an active ingredient concentration of 0.01 to 10,000 ppm, and applied. Powders, etc. are usually applied as they are.
  • formulations and their dilutions may be sprayed directly onto plants, such as harmful arthropods or crops to be protected from harmful arthropods, and harmful arthropods that inhabit the soil of cultivated land
  • the soil may be treated to control.
  • the resin preparation processed into a sheet or string can be treated by a method such as wrapping around a crop, spreading it in the vicinity of a crop, spreading it on stock soil, or the like.
  • the amount of the compound applied is usually 0.01 to 10% of the compound of the present invention per 1 m 2 of treated area when treated on a surface.
  • the amount of the compound of the present invention per 1 m 3 of treatment space is usually 0.01 to 500 mg when treated in a space.
  • the composition of the present invention is formulated into an emulsion, a wettable powder, a flowable and the like, it is usually diluted with water so as to have an active ingredient concentration of 0.1 to 10,000 ppm, and applied. Apply the agent, fuming agent, poison bait etc. as it is.
  • composition of the present invention When the composition of the present invention is used to control ectoparasites of small animals such as cattle, horses, pigs, sheep, goats, chickens, etc., dogs, cats, rats, mice, etc. It can be used.
  • systemic suppression for example, it is administered by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal etc.) and is intended for non-systemic suppression.
  • oil or aqueous solution is sprayed, pour-on treatment or spot-on treatment is performed, the animal is washed with a shampoo preparation, or the resin preparation is used as a collar or ear tag and attached to the animal.
  • the amount of the compound of the present invention when administered to animals is usually in the range of 0.1 to 1,000 mg per kg of animal weight.
  • composition of the present invention can be used as a control agent for harmful arthropods in agricultural land such as fields, paddy fields, lawns, orchards and the like.
  • the composition of the present invention can control harmful arthropods such as the agricultural land in the agricultural land where the plants listed below are cultivated.
  • Agricultural products corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugar cane, tobacco etc.
  • Vegetables Solanaceous vegetables (eggplant, tomato, pepper, pepper, potato), Cucurbita vegetables (eg, cucumber, pumpkin, zucchini, watermelon, melon), Brassica vegetables (Japanese radish, turnip, horseradish, horse mackerel, Chinese cabbage) , Cabbage, mustard, broccoli, cauliflower etc), Asteraceae vegetables (burdock, shung chrysanthemum, artichoke, lettuce etc), Liliaceae vegetables (Leeks, onions, garlic, asparagus), Seriaceae vegetables (carrot, parsley, celery, American Bofffew, etc.), vulgare family vegetables (spinach, swiss chard etc.), sage family vegetables (sesame, mint, basil etc.), strawberries
  • Trees other than fruit trees tea, mulberry, flowering trees, street trees (astera, birch, dogwood, eucalyptus, eucalyptus, ginkgo, lilac, maple, oak, poplar, persimmon, perennial, fusarium, plananas, persimmon, perianthus, birch, fir tree, tsuga, nezu Spruce, yew) etc.
  • the above-mentioned plants also include plants which can be produced by natural mating, plants which can be generated by mutation, F1 hybrid plants and genetically modified crops.
  • genetically modified crops include HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutole, ALS (acetolactate synthetase) inhibitors such as imazethapyr and thifensulfuron methyl, EPSP (5 -Plants with resistance to herbicides such as -enolpyruvyl shikimate-3-phosphate synthetase inhibitor, glutamine synthetase inhibitor, PPO (protoporphyrinogen oxidase) inhibitor, bromoxynil, or dicamba
  • HPPD 4-hydroxyphenylpyruvate dioxygenase enzyme
  • ALS acetolactate synthetase
  • EPSP -Plants with resistance to herbicides such as -enolpyruvyl
  • the above-mentioned plant is not particularly limited as long as it is a commonly grown variety.
  • Reference Production Example 8 The compounds produced according to Reference Production Example 7 and the physical properties thereof are shown below.
  • Formula (A-1) In the compounds shown by, the combination of R 1 and R is any combination described in [Table 4].
  • Production Example 2 The compounds produced according to Production Example 1 and the physical properties thereof are shown below.
  • Formula (A-2) In the compounds shown by, the combination of R 1 and R is any combination described in [Table 5].
  • the present compound 2 1 H-NMR (CDCl 3 ) ⁇ : 8.30 (1 H, d), 8. 19 (1 H, d), 7. 75 (1 H, dd), 7. 66 (1 H, d), 7.32 (1 H, d), 3.02 (2H, q), 1.48 (9H, s), 1.47 (3H, t).
  • the present compound 3 1 H-NMR (CDCl 3 ) ⁇ : 8.29 (1 H, d), 8.23 (1 H, d), 7.69-7.69 (2 H, m), 7.32 (1 H, d), 3.02 (2 H, q ), 1.48 (9H, s), 1.48 (3H, t).
  • Production Example 4 The compounds produced according to Production Example 3 and the physical properties thereof are shown below.
  • Formula (A-3) And in the compound represented by, the combination of R 1 and R is any combination described in [Table 6].
  • the present compound 6 1 H-NMR (CDCl 3 ) ⁇ : 8.66 (1H, d), 8.15 (1H, d), 8.13 (1H, d), 7.77 (1H, d), 7.72 (1H, dd), 4.05 (2H, q), 1.54 (9H, s), 1.43 (3H, t).
  • the present compound 7 1 H-NMR (CDCl 3 ) ⁇ : 8.66 (1H, d), 8.16-8.15 (2H, m), 7.74-7.71 (2H, m), 4.05 (2H, q), 1.54 (9H , s), 1.41 (3H, q).
  • the present compound 8 1 H-NMR (CDCl 3 ) ⁇ : 8.67 (1 H, d), 8.32 (1 H, d), 8. 15 ( 1 H, d), 7. 90 (1 H, d), 7. 86 (1 H, dd), 4.05 (2H, q), 1.55 (9H, s), 1.44 (3H, t).
  • the present compound 9 1 H-NMR (CDCl 3 ) ⁇ : 8.74 (1H, d), 8.58 (1H, d), 8.22 (1H, d), 8.17 (1H, dd), 7.95 (1H, d), 4.02 (2H, q), 1.64 (6H, s), 1.45 (3H, t).
  • the present compound 10 1 H-NMR (CDCl 3 ) ⁇ : 8.65 (1 H, d), 8.12 (1 H, d), 8.01 (1 H, d), 7. 76 (1 H, d), 7.71 (1 H, dd), 4.29 (2H, q), 4.06 (2H, q), 1.54 (3H, t), 1.44 (3H, t).
  • the present compound 11 1 H-NMR (CDCl 3 ) ⁇ : 8.65 (1 H, d), 8.55 (1 H, d), 8. 14 (1 H, dd), 8.01 (1 H, d), 7. 93 (1 H, d), 4.30 (2H, q), 4.03 (2H, q), 1.54 (3H, t), 1.45 (3H, t).
  • the present compound 12 1 H-NMR (CDCl 3 ) ⁇ : 8.66 (1H, d), 8.55 (1H, d), 8.14 (1H, dd), 8.02 (1H, d), 7.93 (1H, d), 4.18 (2H, t), 4.03 (2H, q), 1.95-1.92 (2H, m), 1.45 (3H, t), 1.12 (3H, t).
  • Invention compound 13 1 H-NMR (CDCl 3 ) ⁇ : 8.62 (1H, d), 8.54 (1H, d), 8.14 (1H, dd), 7.99 (1H, d), 7.93 (1H, d), 4.86-4.80 (1 H, m), 4.04 (2 H, q), 1. 48 (6 H, d), 1.
  • the present compound 17 1 H-NMR (CDCl 3 ) ⁇ : 8.65 (1H, d), 8.15 (1H, d), 8.01 (1H, d), 7.74-7.71 (2H, m), 4.16 (2H, t) ), 4.07 (2H, q), 1.94-1.91 (2H, m), 1.44 (3H, t), 1.11 (3H, t).
  • the present compound 18 1 H-NMR (CDCl 3 ) ⁇ : 8.60 ( 1 H, d), 8. 15 (1 H, d), 7.99 (1 H, d), 7.74-7.70 (2 H, m), 4.86-4. 77 (1 H , m), 4.07 (2H, q), 1.46 (6H, d), 1.43 (3H, t).
  • the present compound 19 1 H-NMR (CDCl 3 ) ⁇ : 8.65 (1H, d), 8.12 (1H, s), 8.01 (1H, d), 7.76 (1H, d), 7.71 (1H, d), 4.16 (2 H, t), 4.06 (2 H, q), 1.95-1. 91 (2 H, m), 1. 44 (3 H, t), 1. 11 (3 H, t).
  • the present compound 20 1 H-NMR (CDCl 3 ) ⁇ : 8.61 (1H, d), 8.12 (1H, d), 7.99 (1H, d), 7.76 (1H, d), 7.71 (1H, dd), 4.87-4.78 (1H, m), 4.07 (2H, q), 1.47 (6H, d), 1.44 (3H, t).
  • the present compound 21 1 H-NMR (CDCl 3 ) ⁇ : 8.65 (1H, d), 8.31 (1H, s), 8.01 (1H, d), 7.90 (1H, d), 7.85 (1H, d), 4.29 (2H, q), 4.06 (2H, q), 1.55 (3H, t), 1.44 (3H, t).
  • the present compound 22 1 H-NMR (CDCl 3 ) ⁇ : 8.66 (1 H, d), 8.32 (1 H, d), 8.02 (1 H, d), 7. 90-7. 85 (2 H, m), 4. 17 (2 H, t ), 4.06 (2H, q), 1.95-1.92 (2H, m), 1.45 (3H, t), 1.11 (3H, t).
  • Invention compound 23 1 H-NMR (CDCl 3 ) ⁇ : 8.61 (1H, d), 8.31 (1H, d), 8.00 (1H, d), 7.90-7.85 (2H, m), 4.87-4.78 (1H , m), 4.06 (2H, q), 1.47 (6H, d), 1.44 (3H, t).
  • the present compound 64 1 H-NMR (CDCl 3 ) ⁇ : 8.64 (1H, d), 8.01 (1H, d), 7.69 (1H, d), 7.66 (1H, d), 7.32 (1H, dd), 4.16 (2H, t), 4.06 (2H, q), 1.94-1.91 (2H, m), 1.43 (3H, t), 1.11 (3H, t).
  • the present compound 65 1 H-NMR (CDCl 3 ) ⁇ : 8.60 (1 H, d), 7. 98 (1 H, d), 7. 69 (1 H, d), 7. 66 (1 H, d), 7.31 (1 H, dd), 4.86-4.77 (1 H, m), 4.06 (2 H, q), 1.48-1.40 (9 H, m).
  • the present compound 24 1 H-NMR (CDCl 3 ) ⁇ : 8.76 ( 1 H, d), 8. 73 (1 H, d), 8. 30 (1 H, d), 8.04 (1 H, d), 6.08 (1 H, tt), 4.62 (2H, t), 3.89 (2H, q), 3.87 (3H, s), 1.39 (3H, t).
  • Production Example 8 The compounds produced according to Production Example 7 and the physical properties thereof are shown below.
  • Formula (A-5) In the compounds represented by, R 2 is any compound described in [Table 8].
  • the present compound 25 1 H-NMR (CDCl 3 ) ⁇ : 8.75 (1H), 8.70 (1H, d), 8.30 (1H, d), 7.94 (1H, d), 4.18 (2H), 3.90-3.83 ( 5H, m), 1.58-1.53 (2H, m), 1.38 (3H, t), 1.26-1.20 (2H, m).
  • the present compound 26 1 H-NMR (CDCl 3 ) ⁇ : 8.76 (1 H, d), 8. 74 (1 H, d), 8.31 (1 H, s), 8.04 (1 H, d), 4. 68 (2 H, t), 3.89 (2H, q), 3.87 (3H, s), 1.39 (3H, t).
  • the present compound 27 1 H-NMR (CDCl 3 ) ⁇ : 8.76 (1 H, d), 8. 73 (1 H, d), 8.31 (1 H, d), 8.04 (1 H, d), 5.26-5.15 (1 H, m ), 4.71-4.55 (2H, m), 3.91 (2H, q), 3.87 (3H, s), 1.39 (3H, t).
  • the present compound 28 1 H-NMR (CDCl 3 ) ⁇ : 8.76 ( 1 H, d), 8. 74 (1 H, d), 8. 30 (1 H, d), 8.04 (1 H, d), 4.71 (2 H, t), 3.90 (2H, q), 3.87 (3H, s), 1.39 (3H, t).
  • the present compound 29 1 H-NMR (CDCl 3 ) ⁇ : 8.75 (1 H, s), 8. 65 (1 H, d), 8. 29 ( 1 H, d), 7. 95 (1 H, d), 4. 27 (2 H, t), 3.85 (3H, s), 3.85 (2H, q), 2.41-2.39 (2H, m), 2.24-2.18 (2H, m), 1.37 (3H, t).
  • the present compound 30 1 H-NMR (CDCl 3 ) ⁇ : 8.76 ( 1 H, d), 8. 71 (1 H, d), 8.
  • the present compound 34 1 H-NMR (CDCl 3 ) ⁇ : 8.75 (1H, d), 8.71 (1H, d), 8.30 (1H, d), 8.01 (1H, d), 6.20 (1H, tt), 4.44 (2H, td), 3.86 (2H, q), 3.86 (3H, s), 1.38 (3H, t).
  • the present compound 35 1 H-NMR (CDCl 3 ) ⁇ : 8.75 (1H, d), 8.63 (1H, d), 8.30 (1H, d), 7.94 (1H, d), 4.27 (2H, q), 3.86-3.81 (5H, m), 1.54 (3H, t), 1.36 (3H, t).
  • the present compound 36 1 H-NMR (CDCl 3 ) ⁇ : 8.74 (1H, d), 8.64 (1H, d), 8.30 (1H, d), 7.94 (1H, d), 4.16 (2H, t), 3.87-3.80 (5H, m), 1.9-1.87 (2H, m), 1.37 (3H, t), 1.11 (3H, t).
  • the present compound 37 1 H-NMR (CDCl 3 ) ⁇ : 8.74 (1H, dd), 8.59 (1H, d), 8.29 (1H, dd), 7.92 (1H, d), 4.84-4.78 (1H, m) ), 3.87-3.79 (5H, m), 1.47 (6H, d), 1.37 (3H, t).
  • the present compound 38 1 H-NMR (CDCl 3 ) ⁇ : 8.74 (1H, d), 8.63 (1H, d), 8.29 (1H, d), 7.94 (1H, d), 4.20 (2H, t), 3.84 (3H, s), 3.83 (2H, q), 1.92-1.85 (2H, m), 1.61-1.52 (2H, m), 1.37 (3H, t), 1.03 (3H, t).
  • the present compound 39 1 H-NMR (CDCl 3 ) ⁇ : 8.74 (1H, d), 8.63 (1H, d), 8.29 (1H, d), 7.93 (1H, d), 4.19 (2H, t), 3.84 (3H, s), 3.83 (2H, q), 1.94-1.87 (2H, m), 1.49-1.44 (4H, m), 1.37 (3H, t), 0.97 (3H, t).
  • the present compound 40 1 H-NMR (CDCl 3 ) ⁇ : 8.74 ( 1 H, d), 8. 59 (1 H, d), 8. 28 (1 H, d), 7.
  • the present compound 42 1 H-NMR (CDCl 3 ) ⁇ : 8.74 (1H, d), 8.65 (1H, d), 8.29 (1H, d), 7.94 (1H, d), 3.84 (3H, s), 3.84 (2H, q), 3.82 (2H, s), 1.38 (3H, t), 1.12 (9H, s).
  • Invention compound 43 1 H-NMR (CDCl 3 ) ⁇ : 8.74 ( 1 H, d), 8. 60 (1 H, d), 8. 28 (1 H, d), 7. 91 (1 H, d), 4.44-4.
  • Invention compound 45 1 H-NMR (CDCl 3 ) ⁇ : 8.75 (1H, d), 8.64 (1H, d), 8.29 (1H, d), 8.08 (1H, d), 3.87 (3H, s), 3.82 (2H, q), 1.54 (9H, s), 1.36 (3H, t).
  • the present compound 46 1 H-NMR (CDCl 3 ) ⁇ : 8.75 (1 H, d), 8. 71 (1 H, d), 8. 29 (1 H, d), 8.09 (1 H, d), 4.95 (2 H, s), 3.86 (3H, s), 3.83 (2H, q), 2.67 (1H, s), 1.38 (3H, t).
  • Invention compound 47 1 H-NMR (CDCl 3 ) ⁇ : 8.74 (1 H, s), 8.62 (1 H, s), 8. 28 (1 H, s), 7. 95 (1 H, s), 5. 96-5. 87 (1 H, m ), 5.42-5.33 (2H, m), 5.05-5.02 (1H, m), 3.88 (2H, q), 3.85 (3H, s), 1.58 (3H, d), 1.35 (3H, t).
  • the present compound 48 1 H-NMR (CDCl 3 ) ⁇ : 8.72 ( 1 H, s), 8. 64 (1 H, s), 8. 27 (1 H, s), 7. 96 (1 H, s), 4.37-4.
  • the present compound 50 1 H-NMR (CDCl 3 ) ⁇ : 8.74 (1H, d), 8.66 (1H, d), 8.29 (1H, d), 7.96 (1H, d), 6.10-6.06 (1H, m) ), 5.52-5.45 (2H, m), 4.79-4.78 (2H, m), 3.88-3.82 (5H, m), 1.36 (3H, t).
  • Invention compound 51 1 H-NMR (CDCl 3 ) ⁇ : 8.74 ( 1 H, d), 8. 64 (1 H, d), 8. 29 (1 H, d), 7. 95 (1 H, d), 5. 96-5.
  • the present compound 55 1 H-NMR (CDCl 3 ) ⁇ : 8.77 (1H, d), 8.71 (1H, d), 8.30 (1H, d), 8.16 (1H, d), 3.88 (3H, s), 3.86 (2H, q), 1.63 (6H, s), 1.37 (3H, t).
  • the present compound 56 1 H-NMR (CDCl 3 ) ⁇ : 8.75 ( 1 H, d), 8. 69 (1 H, d), 8. 30 (1 H, d), 8.01 (1 H, d), 4. 39-4. 35 (2 H, m ), 3.89-3.80 (7H, m), 3.48 (3H, s), 1.36 (3H, t).
  • the present compound 57 1 H-NMR (CDCl 3 ) ⁇ : 8.75 ( 1 H, d), 8. 71 (1 H, d), 8. 30 (1 H, d), 8.01 (1 H, d), 4. 36 (2 H, t), 3.87 (2H, q), 3.86 (3H, s), 1.85 (3H, t), 1.38 (3H, t).
  • Invention compound 58 1 H-NMR (CDCl 3 ) ⁇ : 8.76-8.73 (2H, m), 8.29 (1 H, d), 8.14 (1 H, d), 5. 39 (2 H, s), 3. 86 ( 3 H, s) ), 3.82 (2H, q), 3.56 (3H, s), 1.37 (3H, t).
  • the present compound 60 1 H-NMR (CDCl 3 ) ⁇ : 8.63 (1H, d), 8.45 (1H, d), 7.90 (2H, dd), 4.28 (2H, q), 4.25 (3H, s), 3.70 (2H, q), 1.54 (3H, t), 1.35 (3H, t).
  • the present compound 61 1 H-NMR (CDCl 3 ) ⁇ : 8.64 (1 H, d), 8. 45 (1 H, d), 7. 91 (1 H, d), 7. 91 (1 H, d), 4. 25 (3 H, s), 4.16 (2H, t), 3.70 (2H, q), 1.95-1.92 (2H, m), 1.36 (3H, t), 1.12 (3H, t).
  • the present compound 62 1 H-NMR (CDCl 3 ) ⁇ : 8.72 (1 H, s), 8. 47 (1 H, s), 8.13 (1 H, s), 7. 92 (1 H, s), 4. 29 (3 H, s), 3.72 (2H, q), 1.64 (6H, s), 1.36 (3H, t).
  • a part represents a weight part.
  • Formulation example 1 10 parts of any one of the compounds 1 to 65 of the present invention is mixed in a mixture of 35 parts of xylene and 35 parts of DMF, and 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzene sulfonate are added thereto and mixed To obtain a formulation.
  • Formulation example 2 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of wet silica and 54 parts of diatomaceous earth are mixed, and further 20 parts of any one of the compounds of the present invention 1 to 65 is added and mixed to obtain a preparation.
  • Formulation example 3 1 part of wet silica, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are added to 2 parts of any one compound of the present invention 1 to 65 and mixed. Then, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated with a granulator and blow-dried to obtain a preparation.
  • Formulation example 4 1 part of any one of the compounds 1 to 65 of the present invention is mixed with an appropriate amount of acetone, 5 parts of wet silica, 0.3 parts of isopropyl acid phosphate and 93.7 parts of kaolin clay are added thereto and thoroughly mixed The acetone is evaporated off to obtain the preparation.
  • Formulation example 5 A formulation is prepared by thoroughly mixing 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and wet silica (weight ratio 1: 1), 20 parts of any one of the compounds of the present invention 1 to 65, and 45 parts of water Get
  • Formulation Example 6 0.1 part of any one of the compounds 1 to 65 of the present invention is mixed with a mixture of 5 parts of xylene and 5 parts of trichloroethane, and this is mixed with 89.9 parts of kerosene to obtain a preparation.
  • Formulation example 7 10 mg of any one of the compounds 1 to 65 of the present invention is mixed with 0.5 mL of acetone, and this solution is added dropwise to 5 g of solid feed powder for animals (solid feed powder for rearing and breeding CE-2 manufactured by CLEA Japan, Inc.) And mix uniformly. The acetone is then evaporated to dryness to obtain a toxic bait.
  • Formulation Example 8 0.1 parts of any one of the compounds 1 to 65 of the present invention and 49.9 parts of neothiozole (manufactured by Chuo Kasei Co., Ltd.) are put into an aerosol can, fitted with an aerosol valve, and filled with 25 parts of dimethyl ether and 25 parts of LPG. Shake is applied and the actuator is mounted to obtain an oil aerosol.
  • Formulation Example 9 0.6 parts of any one of the compounds 1 to 65 of the present invention, 0.01 parts of 2,6-di-tert-butyl-4-methylphenol, 5 parts of xylene, 3.39 parts of kerosene and an emulsifier ⁇ Leodol MO- 60 parts (made by Kao Corporation) and 50 parts of distilled water are filled in an aerosol container, and after mounting a valve, 40 parts of propellant (LPG) is pressure-filled through the valve. Obtain an aqueous aerosol.
  • LPG propellant
  • Formulation Example 10 0.1 g of any one of the compounds 1 to 65 of the present invention is mixed with 2 mL of propylene glycol and impregnated into a 4.0 cm ⁇ 4.0 cm, 1.2 cm thick ceramic plate, and a heating smoke agent is added. obtain.
  • Formulation example 11 5 parts of any one of the compounds 1 to 65 of the present invention and ethylene-methyl methacrylate copolymer (the ratio of methyl methacrylate to the total weight of the copolymer: 10% by weight, Aclift (registered trademark) WD 301, manufactured by Sumitomo Chemical Co., Ltd. 95 parts are melt-kneaded with a closed type pressure kneader (manufactured by Moriyama Seisakusho), and the obtained kneaded product is extruded from an extrusion molding machine through a molding die to obtain a rod-shaped molding having a length of 15 cm and a diameter of 3 mm.
  • a closed type pressure kneader manufactured by Moriyama Seisakusho
  • Formulation example 12 5 parts of any one of the compounds 1 to 65 of the present invention and 95 parts of a soft vinyl chloride resin are melt-kneaded with a closed-type pressure kneader (manufactured by Moriyama Seisakusho), and the obtained kneaded product is extruded through an extrusion molding machine The mixture is extruded to obtain a rod-shaped molding having a length of 15 cm and a diameter of 3 mm.
  • a closed-type pressure kneader manufactured by Moriyama Seisakusho
  • Formulation example 13 100 mg of any one of the compounds 1 to 65 of the present invention, 68.75 mg of lactose, 237.5 mg of corn starch, 43.75 mg of microcrystalline cellulose, 18.75 mg of polyvinylpyrrolidone, 28.75 mg of sodium carboxymethyl starch, and magnesium stearate 2.5 mg are mixed and the resulting mixture is compressed to a suitable size to obtain tablets.
  • Formulation example 14 25 mg of any one of the compounds 1 to 65 of the present invention, 60 mg of lactose, 25 mg of corn starch, 6 mg of carmellose calcium, and 5% hydroxypropyl methylcellulose, and mixed appropriately to obtain hard shell gelatin capsule or hydroxypropyl methylcellulose capsule To give capsules.
  • Formulation example 15 100 mg of any one of the compounds 1 to 65 of the present invention, 500 mg of fumaric acid, 2,000 mg of sodium chloride, 150 mg of methylparaben, 50 mg of propylparaben, 25,000 mg of granular sugar, 13,000 mg of sorbitol (70% solution), Veegum (registered trademark) To 100 mg of K (Vanderbilt Co.), 35 mg of perfume and 500 mg of coloring matter, distilled water is added to a final volume of 100 ml and mixed to obtain a suspension for oral administration.
  • Formulation example 16 5% by weight of any one of the compounds 1 to 65 of the present invention is mixed with 5% by weight of an emulsifier, 3% by weight of benzyl alcohol and 30% by weight of propylene glycol, and the pH of this solution is 6.0 to 6.5. After adding the phosphate buffer solution as it becomes, water is added as the balance to obtain a solution for oral administration.
  • Formulation example 17 5% by weight of aluminum distearate is added to 57% by weight of fractionated palm oil and 3% by weight of polysorbate 85 and dispersed by heating. It is cooled to room temperature and 25% by weight of saccharin is dispersed in the oily vehicle. To this, 10% by weight of any one of the compounds of the present invention 1 to 65 is distributed to obtain a paste-form preparation for oral administration.
  • Formulation example 18 5% by weight of any one of the compounds 1 to 65 of the present invention is mixed with 95% by weight of limestone powder to obtain granules for oral administration using a wet granulation method.
  • Formulation example 19 Five parts of any one of the compounds 1 to 65 of the present invention is mixed with 80 parts of diethylene glycol monoethyl ether, and 15 parts of propylene carbonate is mixed therewith to obtain a spot-on solution.
  • Formulation example 20 Ten parts of any one of the compounds 1 to 65 of the present invention is mixed with 70 parts of diethylene glycol monoethyl ether, and 20 parts of 2-octyldodecanol is mixed therewith to obtain a pour-on liquid agent.
  • Formulation example 21 To 0.5 part of any one of the compounds 1 to 65 of the present invention, 60 parts of NIKKOL® TEALS-42 (A 42% aqueous solution of Nikko Chemicals' triethanolamine lauryl sulfate triethanolamine) and 20 parts of propylene glycol are added After thoroughly mixing with stirring to obtain a uniform solution, 19.5 parts of water is added and the mixture is further sufficiently stirred and mixed to obtain a shampoo solution of a uniform solution.
  • NIKKOL® TEALS-42 A 42% aqueous solution of Nikko Chemicals' triethanolamine lauryl sulfate triethanolamine
  • Formulation example 22 0.15% by weight of any one of the compounds 1 to 65 of the present invention, 95% by weight of animal feed, and 4.85% by weight of a mixture consisting of calcium phosphate dibasic, diatomaceous earth, Aerosil (registered trademark), and carbonate (or chalk) Mix thoroughly to obtain an animal feed premix.
  • Formulation example 23 7.2 g of any one of the compounds 1 to 65 of the present invention and 92.8 g of FOSCO S-55 (manufactured by Maruishi Pharmaceutical Co., Ltd.) are mixed at 100 ° C., poured into a suppository form, and cooled and solidified And get a suppository.
  • test examples the efficacy of the compounds of the present invention against harmful arthropods is shown by test examples.
  • the test was performed at 25 ° C.
  • Test Example 1 A test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Syndyne (registered trademark) is added thereto to prepare a diluted solution containing a predetermined concentration of the test compound. About 30 cotton aphids (all stages) are inoculated to cucumber (Cucumis sativus) seedlings (the second true leaf development stage) planted in a container. One day later, the seedlings are sprayed with the diluted solution at a rate of 10 mL / seedling. After 5 days, the number of surviving insects is examined, and the control value is determined by the following equation.
  • Syndyne registered trademark
  • Control value (%) ⁇ 1- (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • Cb Number of tested insects in untreated area
  • Cai Number of surviving insects in survey in untreated area
  • Tb Number of tested insects in treated zone
  • Tai Number of surviving insects in survey in treated area
  • untreated group means It means a zone that performs the same operation as the treatment zone except that the test compound is not used.
  • the test was conducted according to Test Example 1 using the present invention compound described below as a test compound with a predetermined concentration of 200 ppm. As a result, all the present invention compounds described below exhibited a control value of 90% or more.
  • the compounds of the present invention 7, 8, 9, 11, 12, 13, 13, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 29, 30, 31, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 49, 50, 51, 54, 55, 56, 57, 59, 60, 61 and 62
  • untreated group means It means a zone that performs the same operation as the treatment zone except that the test compound is not used.
  • the test of the present invention was conducted according to Test Example 2 using a compound of the present invention described below as a test compound at a predetermined concentration of 1,000 ppm. As a result, the compound of the present invention showed a control value of 90% or more.
  • Compounds of the present invention 24, 25, 30, 31, 32, 33, 34, 35, 36, 37, 40, 43, 45, 49, 50, 56, 57, 59, 60, 61 and 62
  • the test was conducted according to Test Example 3 using the following compound of the present invention as a test compound with a predetermined concentration of 500 ppm. As a result, all of the following compounds of the present invention showed a control value of 90% or more.
  • the compound of the present invention 22, 23, 24, 27, 55 and 62
  • test was conducted according to Test Example 3 using a compound of the present invention described below as a test compound with a predetermined concentration of 200 ppm. As a result, each of the compounds of the present invention described below exhibited a control value of 90% or more.
  • the compound of the present invention 55 and 62
  • the compound of the present invention described below exhibited a control value of 90% or more.
  • Test Example 5 A test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Syndyne (registered trademark) is added thereto to prepare a diluted solution containing a predetermined concentration of the test compound.
  • the diluted solution is sprayed at a rate of 20 mL / seedling to cabbage (Brassicae oleracea) seedlings (second to third leaf development stage) planted in a container. After that, the stems and leaves of this seedling are cut and placed in a container covered with filter paper. Release 5 2nd instar larvae to this. After 5 days, the number of living worms is counted, and the mortality rate is calculated from the following equation.
  • Mortality rate% (1-number of surviving insects / 5) x 100
  • test Example 5 The test was conducted according to Test Example 5 using a compound of the present invention described below as a test compound at a predetermined concentration of 500 ppm. As a result, each of the compounds of the present invention described below showed a mortality of 80% or more.
  • Inventive compounds 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 24, 26, 27, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 44, 45, 48, 49, 50, 51, 55, 56, 57, 59, 60, 61, 62, 63, 64 and 65
  • Test Example 6 A test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Syndyne (registered trademark) is added thereto to prepare a diluted solution containing a predetermined concentration of the test compound.
  • the diluted solution is sprayed at a rate of 20 mL / seedling to cabbage (Brassicae oleracea) seedlings (second to third leaf development stage) planted in a container. After that, the stems and leaves of this seedling are cut and placed in a container covered with filter paper. Release five 2nd instar larvae to this. After 5 days, the number of living worms is counted, and the mortality rate is calculated from the following equation.
  • Mortality rate% (1-number of surviving insects / 5) x 100
  • test Example 6 The test was conducted according to Test Example 6 using a compound of the present invention described below as a test compound with a predetermined concentration of 500 ppm. As a result, each of the compounds of the present invention described below showed a mortality of 80% or more.
  • Inventive compounds 1, 4, 5, 6, 7, 8, 9, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 24, 26, 27, 29, 30, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 44, 45, 45, 47, 48, 49, 50, 51, 55, 56, 57, 59, 60, 61, 62, 63, 64 and 65
  • the test was conducted according to Test Example 7 using a compound of the present invention described below as a test compound with a predetermined concentration of 200 ppm. As a result, all of the compounds of the present invention described below showed a mortality of 90% or more.
  • the present invention compounds 4, 5, 6, 7, 8, 9, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 29, 30, 31, 32, 23, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 45, 48, 49, 50, 51, 55, 56, 57, 59, 60, 61 and 62
  • Test Example 8 The test was conducted according to Test Example 8 using the following compound of the present invention as a test compound with a predetermined concentration of 500 ppm. As a result, all of the following compounds of the present invention exhibited a mortality of 80% or more.
  • Inventive compounds 5,7,8,9,13,14,16,24,25,26,28,29,30,31,32,33,34,38,39,41,45,48, 51, 55 and 57
  • the test was conducted according to Test Example 9 using a compound of the present invention described below as a test compound with a predetermined concentration of 500 ppm. As a result, each of the compounds of the present invention described below showed a mortality of 100%.
  • the compounds of the present invention 21, 23, 24, 25, 26, 30, 31, 33, 34, 49, 55 and 57
  • test Example 10 The test was conducted according to Test Example 10 using a compound of the present invention described below as a test compound with a predetermined concentration of 500 ppm. As a result, each of the compounds of the present invention described below showed a mortality of 100%.
  • Prepare diluent B containing the concentration. Dilution A and dilution B are mixed to obtain dilution C.
  • Dilution C wherein the concentration of the compound of the present invention is 200 ppm and the concentration of this component is 2,000 ppm among the combinations described in List A.
  • Comp X means any one compound selected from the compounds of the present invention 1 to 65.
  • Dilution C wherein the concentration of the compound of the present invention is 200 ppm and the concentration of this component is 200 ppm in the combinations described in List A.
  • Dilution C wherein the concentration of the compound of the present invention is 500 ppm and the concentration of this component is 5 ppm in the combinations described in List A.
  • Dilution C wherein the concentration of the compound of the present invention is 500 ppm and the concentration of this component is 0.5 ppm in the combinations described in List A.
  • the compounds of the present invention exhibit excellent control effects against harmful arthropods.

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Abstract

The present invention provides: a compound represented by formula (I) that has an excellent controlling effect against harmful arthropods [in the formula, A1 represents NCH3 or the like, A2 represents a nitrogen atom or the like, R1 represents a C1-C3 perfluoroalkyl group or the like, R2 represents a C2-C5 chain hydrocarbon group optionally having one or more halogen atoms or the like, n represents 0 or the like. Group X: group consisting of a cyano group and a halogen atom.]; a production intermediate thereof; a composition containing the compound; and a composition containing the compound, one or more components selected from the group consisting of group (a) and group (b), and an inert carrier.

Description

複素環化合物及びそれを含有する有害節足動物防除剤Heterocyclic compound and harmful arthropod controlling agent containing the same
　本特許出願は日本国特許出願２０１７－１８４４６４号（２０１７年９月２６日出願）および２０１７－２４５９５８号（２０１７年１２月２２日出願）に基づくパリ条約上の優先権および利益を主張するものであり、ここに引用することによって、上記出願に記載された内容の全体が、本明細書中に組み込まれるものとする。
　本発明はある種の複素環化合物及びその有害節足動物防除剤に関する。 This patent application claims priority and benefit under the Paris Convention under Japanese Patent Applications 2017-184464 (filed on September 26, 2017) and 2017-245958 (filed on December 22, 2017). The entire contents of the above application are incorporated herein by reference.
The present invention relates to certain heterocyclic compounds and their harmful arthropod controlling agents.
　これまでに有害節足動物の防除を目的として、様々な化合物が検討されており、実用に供されている。
　また、ある種の化合物が有害生物防除効果を有することが知られている（例えば、特許文献１参照）。 So far, various compounds have been studied and put to practical use for the purpose of controlling harmful arthropods.
In addition, it is known that certain compounds have pest control effects (see, for example, Patent Document 1).
国際公開第２０１３／０１８９２８号International Publication No. 2013/018928
　本発明は、有害節足動物に対して優れた防除効力を有する化合物を提供することを課題とする。 An object of the present invention is to provide a compound having excellent control efficacy against harmful arthropods.
　本発明者は、有害節足動物に対して優れた防除効力を有する化合物を見出すべく検討した結果、下記式（Ｉ）で示される化合物が有害節足動物に対して優れた防除効力を有することを見出した。
　すなわち、本発明は、以下のとおりである。
［１］　式（Ｉ）：
Figure JPOXMLDOC01-appb-C000003
 ［式中、
　Ａ１は、ＮＣＨ３、酸素原子又は硫黄原子を表し、
　Ａ２は、窒素原子又はＣＨを表し、
　Ｒ１は、Ｃ１－Ｃ３ペルフルオロアルキル基、Ｃ１－Ｃ３ペルフルオロアルコキシ基、Ｃ１－Ｃ３ペルフルオロアルキルスルファニル基、Ｃ１－Ｃ３ペルフルオロアルキルスルフィニル基、又はＣ１－Ｃ３ペルフルオロアルキルスルホニル基を表し、
　Ｒ２は、１以上のハロゲン原子を有していてもよいＣ２－Ｃ５鎖式炭化水素基、１以上のハロゲン原子を有していてもよい（Ｃ１－Ｃ２アルコキシ）Ｃ１－Ｃ２アルキル基、群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル基、又は（群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル）Ｃ１－Ｃ２アルキル基を表し、
　ｎは、０、１又は２を表す。
　群Ｘ：シアノ基及びハロゲン原子からなる群。］
で示される化合物、又はそのＮ－オキシド（以下、式（Ｉ）で示される化合物又はそのＮ－オキシドを、「本発明化合物」と記す）。
〔２〕　Ｒ２が、１以上のハロゲン原子を有していてもよいＣ２－Ｃ３鎖式炭化水素基、群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル基、又は（群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル）メチル基である、〔１〕記載の化合物。
〔３〕　Ｒ１が、トリフルオロメチル基、トリフルオロメトキシ基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、又はトリフルオロメチルスルホニル基である、〔１〕又は〔２〕記載の化合物。
〔４〕　Ａ１及びＡ２の組み合わせが、Ａ１がＮＣＨ３であり、Ａ２が窒素原子である組み合わせか、又はＡ１が酸素原子であり、Ａ２がＣＨである組み合わせである、〔１〕～〔３〕のいずれか一つに記載の化合物。
〔５〕　Ａ１がＮＣＨ３であり、Ａ２が窒素原子である、〔１〕～〔３〕のいずれか一つに記載の化合物。
〔６〕　Ａ１が酸素原子であり、Ａ２がＣＨである、〔１〕～〔３〕のいずれか一つに記載の化合物。
〔７〕　〔１〕～〔６〕のいずれか一つに記載の化合物と、不活性担体とを含有する有害節足動物防除組成物。
〔８〕　〔１〕～〔６〕のいずれか一つに記載の化合物の有効量を有害節足動物又は有害節足動物の生息場所に施用する有害節足動物の防除方法。
〔９〕　群（ａ）及び群（ｂ）からなる群より選ばれる１以上の成分、並びに〔１〕～〔６〕のいずれか一つに記載の化合物を含有する組成物（以下、「組成物Ａ」と記す）：
　群（ａ）：殺虫活性成分、殺ダニ活性成分及び殺線虫活性成分からなる群；
　群（ｂ）：殺菌活性成分。
〔１０〕　式（Ｘ）：
Figure JPOXMLDOC01-appb-C000004
 ［式中、
　Ｒｘは、ＯＲ２、フッ素原子又は塩素原子を表し、
　Ｒ２は、１以上のハロゲン原子を有していてもよいＣ２－Ｃ５鎖式炭化水素基、１以上のハロゲン原子を有していてもよい（Ｃ１－Ｃ２アルコキシ）Ｃ１－Ｃ２アルキル基、群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル基、又は（群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル）Ｃ１－Ｃ２アルキル基を表し、
　ｎは、０、１又は２を表し、
　Ｒｙは、シアノ基、カルボキシ基、メトキシカルボニル基又はエトキシカルボニル基を表す。
　群Ｘ：シアノ基及びハロゲン原子からなる群。］で示される化合物（以下、「中間体Ｘ」と記す）。
〔１１〕　〔７〕もしくは〔９〕に記載の組成物の有効量を有害節足動物又は有害節足動物の生息場所に施用する有害節足動物の防除方法。
〔１２〕　〔１〕～〔６〕のいずれか一つに記載の化合物の有効量又は〔７〕もしくは〔９〕に記載の組成物の有効量を保持している種子又は栄養生殖器官。 As a result of the present inventor's study to find a compound having excellent control efficacy against harmful arthropods, the compound represented by the following formula (I) has an excellent control activity against harmful arthropods Found out.
That is, the present invention is as follows.
[1] Formula (I):
Figure JPOXMLDOC01-appb-C000003
 [In the formula,
A 1 represents NCH 3 , an oxygen atom or a sulfur atom,
A 2 represents a nitrogen atom or CH,
R 1 represents a C1 to C3 perfluoroalkyl group, a C1 to C3 perfluoroalkoxy group, a C1 to C3 perfluoroalkylsulfanyl group, a C1 to C3 perfluoroalkylsulfinyl group, or a C1 to C3 perfluoroalkylsulfonyl group,
R 2 is a C2-C5 chain hydrocarbon group which may have one or more halogen atoms, (C1-C2 alkoxy) C1-C2 alkyl group which may have one or more halogen atoms, a group A cyclopropyl group which may have one or more substituents selected from X, or (a cyclopropyl group optionally having one or more substituents selected from group X) C1-C2 alkyl group,
n represents 0, 1 or 2;
Group X: a group consisting of a cyano group and a halogen atom. ]
Or a N-oxide thereof (hereinafter, the compound represented by the formula (I) or the N-oxide thereof is referred to as “the compound of the present invention”).
[2] R 2 is a C2-C3 chain hydrocarbon group optionally having one or more halogen atoms, a cyclopropyl group optionally having one or more substituents selected from Group X, or The compound according to [1], which is a (cyclopropyl) methyl group which may have one or more substituents selected from Group X.
[3] The compound according to [1] or [2], wherein R 1 is a trifluoromethyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group.
[4] A combination of A 1 and A 2 is a combination in which A 1 is NCH 3 and A 2 is a nitrogen atom, or a combination in which A 1 is an oxygen atom and A 2 is CH [ The compound as described in any one of 1] to [3].
[5] The compound according to any one of [1] to [3], wherein A 1 is NCH 3 and A 2 is a nitrogen atom.
[6] The compound according to any one of [1] to [3], wherein A 1 is an oxygen atom and A 2 is CH.
[7] A harmful arthropod controlling composition comprising the compound according to any one of [1] to [6] and an inert carrier.
[8] A method for controlling noxious arthropods, which comprises applying an effective amount of the compound according to any one of [1] to [6] to a harmful arthropod or a habitat of the harmful arthropod.
[9] A composition containing one or more components selected from the group consisting of group (a) and group (b), and the compound according to any one of [1] to [6] (hereinafter referred to as “composition Mark as "A"):
Group (a): a group consisting of an insecticidal active ingredient, an acaricidal active ingredient and a nematode active ingredient;
Group (b): bactericidal active ingredient.
[10] Formula (X):
Figure JPOXMLDOC01-appb-C000004
 [In the formula,
R x represents OR 2 , a fluorine atom or a chlorine atom,
R 2 is a C2-C5 chain hydrocarbon group which may have one or more halogen atoms, (C1-C2 alkoxy) C1-C2 alkyl group which may have one or more halogen atoms, a group A cyclopropyl group which may have one or more substituents selected from X, or (a cyclopropyl group optionally having one or more substituents selected from group X) C1-C2 alkyl group,
n represents 0, 1 or 2;
R y represents a cyano group, a carboxy group, a methoxycarbonyl group or an ethoxycarbonyl group.
Group X: a group consisting of a cyano group and a halogen atom. ] Compound (Hereinafter, it is described as "intermediate X") shown.
[11] A method for controlling noxious arthropods, which comprises applying an effective amount of the composition according to [7] or [9] to a harmful arthropod or a habitat of the harmful arthropod.
[12] A seed or vegetative organ which retains an effective amount of the compound according to any one of [1] to [6] or an effective amount of the composition according to [7] or [9].
　本発明により、有害節足動物を防除することができる。また、式（Ｉ）で示される化合物を、例えば式（Ｘ）で示される化合物を中間体として用いて製造することができる。 According to the present invention, harmful arthropods can be controlled. Also, the compound represented by the formula (I) can be produced, for example, using the compound represented by the formula (X) as an intermediate.
　本発明における置換基について説明する。
　「ハロゲン原子」とは、フッ素原子、塩素原子、臭素原子、又はヨウ素原子を意味する。
　置換基が２以上のハロゲン原子を有している場合、それらのハロゲン原子は各々同一でも異なっていてもよい。
　本明細書における「ＣＸ－ＣＹ」との表記は、炭素原子数がＸ乃至Ｙであることを意味する。例えば「Ｃ１－Ｃ６」との表記は、炭素原子数が１乃至６であることを意味する。
　「鎖式炭化水素基」とは、アルキル基、アルケニル基又はアルキニル基を表す。
　「アルキル基」としては、例えばメチル基、エチル基、プロピル基、イソプロピル基、１，１－ジメチルプロピル基、１，２－ジメチルプロピル基、１－エチルプロピル基、ブチル基、ｓｅｃ－ブチル基、ｔｅｒｔ－ブチル基、及びペンチル基が挙げられる。
　「アルケニル基」としては、例えばビニル基、１－プロペニル基、２－プロペニル基、１－メチル－１－プロペニル基、１－メチル－２－プロペニル基、１，２－ジメチル－１－プロペニル基、１－メチル－２－プロペニル基、１－エチル－２－プロペニル基、３－ブテニル基、及び４－ペンテニル基が挙げられる。
　「アルキニル基」としては、例えばエチニル基、１－プロピニル基、２－プロピニル基、１－メチル－２－プロピニル基、１，１－ジメチル－２－プロピニル基、１－エチル－２－プロピニル基、２－ブチニル基、３－ブチニル基、及び４－ペンチニル基が挙げられる。
　「アルコキシ基」とは、アルキル基が酸素原子と結合した１価の基を意味し、例えば、メトキシ基、エトキシ基、プロポキシ基、ブトキシ基、ペントキシ基及びヘキシルオキシ基が挙げられる。
　「１以上のハロゲン原子を有していてもよいＣ２－Ｃ５鎖式炭化水素基」としては、前記「アルキル基」、「アルケニル基」および「アルキニル基」として例示する基に加えて、１以上のハロゲン原子を有するＣ２－Ｃ５鎖式炭化水素基が挙げられる。
　１以上のハロゲン原子を有するＣ２－Ｃ５鎖式炭化水素基としては、例えば１,１－ジメチル－２,２,２－トリフルオロエチル基、２,２,３,３,３－ペンタフルオロプロピル基、２,２,３,３－テトラフルオロプロピル基、２,２,３,４,４,４－ヘキサフルオロブチル基）、２,２,３,３,４,４,４－へプタフルオロブチル基、４,４,４－トリフルオロブチル基、２,２,２－トリフルオロ－１－メチルプロピル基、２,２,２－トリフルオロエチル基、３,３,３－トリフルオロプロピル基、２,２－ジフルオロプロピル基、２－クロロ－ビニル基）、２,２－ジクロロビニル基、２,２,２－トリフルオロブチル基、及び２,２－ジフルオロプロピル基が挙げられる。
　「Ｃ１－Ｃ３ペルフルオロアルキル基」としては、例えばトリフルオロメチル基、ペンタフルオロエチル基、及びへプタフルオロプロピル基が挙げられる。
　「Ｃ１－Ｃ３ペルフルオロアルコキシ基」としては、例えばトリフルオロメトキシ基、ペンタフルオロエトキシ基、及びへプタフルオロプロポキシ基が得られる。
　「Ｃ１－Ｃ３ペルフルオロアルキルスルファニル基」、「Ｃ１－Ｃ３ペルフルオロアルキルスルフィニル基」、及び「Ｃ１－Ｃ３ペルフルオロアルキルスルホニル基」とは、例えばＳ（Ｏ）ｎで示される部分を有するＣ１－Ｃ３ペルフルオロアルキルを表す。
　例えば、ｎが０であるＣ１－Ｃ３ペルフルオロアルキルスルファニル基の例としては、例えばトリフルオロメチルスルファニル基、ペンタフルオロエチルスルファニル基、及びへプタフルオロプロピルスルファニル基を挙げられる。
　例えば、ｎが１であるＣ１－Ｃ３ペルフルオロアルキルスルフィニル基の例としては、例えばトリフルオロメチルスルスルフィニル基、ペンタフルオロエチルスルフィニル基、及びへプタフルオロプロピルスルフィニル基を挙げられる。
　例えば、ｎが２であるＣ１－Ｃ３ペルフルオロアルキルスルホニル基の例としては、例えばトリフルオロメチルスルスルホニル基、ペンタフルオロエチルスルホニル基、及びへプタフルオロプロピルスルホニル基を挙げられる。
　「１以上のハロゲン原子を有していてもよい（Ｃ１－Ｃ２アルコキシ）Ｃ１－Ｃ２アルキル基」とは、（Ｃ１－Ｃ２アルコキシ）及び／又は（Ｃ１－Ｃ２アルキル基）が１以上のハロゲン原子を有していてもよい基を表し、例えば、メトキシメチル基、メトキシエチル基、２－トリフルオロメトキシエチル基、１－エトキシエチル基、２，２－ジフルオロ－２－エトキシエチル基、及び２，２－ジフルオロ－２－トリフルオロメトキシエチル基が挙げられる。
　「群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル基」としては、例えば、シクロプロピル基、１－シアノシクロプロピル基、及び２，２－ジフルオロシクロプロピル基が挙げられる。
　「（群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル）Ｃ１－Ｃ２アルキル基」とは、群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピルが置換したＣ１－Ｃ２アルキル基を表し、例えば、シクロプロピルメチル基、１－シクロプロピルエチル基、２－シクロプロピルエチル基、（１－シアノシクロプロピル）メチル基、及び（２，２－ジフルオロシクロプロピル）メチル基が挙げられる。 The substituents in the present invention will be described.
The "halogen atom" means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
When the substituent has two or more halogen atoms, those halogen atoms may be the same or different.
The notation "CX-CY" in the present specification means that the number of carbon atoms is X to Y. For example, the notation "C1-C6" means that the number of carbon atoms is 1 to 6.
The "chain hydrocarbon group" represents an alkyl group, an alkenyl group or an alkynyl group.
As the “alkyl group”, for example, methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, sec-butyl group, A tert-butyl group and a pentyl group can be mentioned.
As the “alkenyl group”, for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 1-methyl-2-propenyl group, 1-ethyl-2-propenyl group, 3-butenyl group and 4-pentenyl group can be mentioned.
As the “alkynyl group”, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-ethyl-2-propynyl group, Examples include 2-butynyl group, 3-butynyl group, and 4-pentynyl group.
The "alkoxy group" means a monovalent group in which an alkyl group is bonded to an oxygen atom, and examples thereof include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group and a hexyloxy group.
The “C2-C5 chain hydrocarbon group optionally having one or more halogen atoms” is one or more in addition to the groups exemplified as the above “alkyl group”, “alkenyl group” and “alkynyl group” And a C2-C5 chain hydrocarbon group having a halogen atom of
As a C2-C5 chain hydrocarbon group having one or more halogen atoms, for example, 1,1-dimethyl-2,2,2-trifluoroethyl group, 2,2,3,3,3-pentafluoropropyl group 2,2,3,3-tetrafluoropropyl, 2,2,3,4,4,4-hexafluorobutyl)), 2,2,3,3,4,4,4-heptafluorobutyl Group, 4,4,4-trifluorobutyl group, 2,2,2-trifluoro-1-methylpropyl group, 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 2,2-difluoropropyl group, 2-chloro-vinyl group), 2,2-dichlorovinyl group, 2,2,2-trifluorobutyl group, and 2,2-difluoropropyl group.
Examples of the "C1-C3 perfluoroalkyl group" include trifluoromethyl group, pentafluoroethyl group, and heptafluoropropyl group.
As the “C 1 -C 3 perfluoroalkoxy group”, for example, trifluoromethoxy group, pentafluoroethoxy group, and heptafluoropropoxy group can be obtained.
The "C1-C3 perfluoroalkylsulfanyl group", "C1-C3 perfluoroalkylsulfinyl group", and "C1-C3 perfluoroalkylsulfonyl group" mean, for example, a C1-C3 perfluoroalkyl having a portion represented by S (O) n. Represents
For example, examples of C1-C3 perfluoroalkylsulfanyl group in which n is 0 include, for example, trifluoromethylsulfanyl group, pentafluoroethylsulfanyl group, and heptafluoropropylsulfanyl group.
For example, examples of the C1-C3 perfluoroalkylsulfinyl group in which n is 1 include, for example, trifluoromethylsulfinyl group, pentafluoroethylsulfinyl group, and heptafluoropropylsulfinyl group.
For example, examples of the C1-C3 perfluoroalkylsulfonyl group in which n is 2 include, for example, trifluoromethylsulsulfonyl group, pentafluoroethylsulfonyl group, and heptafluoropropylsulfonyl group.
The "(C1-C2 alkoxy) C1-C2 alkyl group which may have one or more halogen atoms" means a halogen atom in which (C1-C2 alkoxy) and / or (C1-C2 alkyl group) is one or more For example, a methoxymethyl group, a methoxyethyl group, a 2-trifluoromethoxyethyl group, a 1-ethoxyethyl group, a 2,2-difluoro-2-ethoxyethyl group, and And 2-difluoro-2-trifluoromethoxyethyl group.
Examples of the “cyclopropyl group optionally having one or more substituents selected from group X” include cyclopropyl group, 1-cyanocyclopropyl group, and 2,2-difluorocyclopropyl group. .
“((Cyclopropyl which may have one or more substituents selected from group X) C1-C2 alkyl group” means cyclopropyl which may have one or more substituents selected from group X Represents a substituted C1-C2 alkyl group, for example, cyclopropylmethyl group, 1-cyclopropylethyl group, 2-cyclopropylethyl group, (1-cyanocyclopropyl) methyl group, and (2,2-difluorocyclo group) And a propyl) methyl group.
　本発明化合物の実施態様としては、以下の化合物が挙げられる。 The following compounds are mentioned as an embodiment of this invention compound.
〔態様１〕本発明化合物において、ｎが２である化合物。
〔態様２〕本発明化合物において、Ｒ２が、１以上のハロゲン原子を有していてもよいＣ２－Ｃ３鎖式炭化水素基、群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル基、又は（群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル）メチル基である化合物。
〔態様３〕態様２において、ｎが２である化合物。
〔態様４〕本発明化合物において、Ｒ２が、Ｃ２－Ｃ３鎖式炭化水素基、シクロプロピル基、又はシクロプロピルメチル基である化合物。
〔態様５〕態様４において、ｎが２である化合物。
〔態様６〕本発明化合物において、Ｒ１が、トリフルオロメチル基、トリフルオロメトキシ基、トリフルオロメチルスルファニル基、トリフルオロメタンスルフィニル基、又はトリフルオロメタンスルホニル基である化合物。
〔態様７〕態様６において、ｎが２である化合物。
〔態様８〕態様６において、Ｒ２が、１以上のハロゲン原子を有していてもよいＣ２－Ｃ３鎖式炭化水素基、群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル基、又は（群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル）メチル基である化合物。
〔態様９〕態様８において、ｎが２である化合物。
〔態様１０〕態様６において、Ｒ２が、Ｃ２－Ｃ３鎖式炭化水素基、又はシクロプロピルメチル基である化合物。
〔態様１１〕態様１０において、ｎが２である化合物。
〔態様１２〕態様６において、Ｒ２が、エチル基、Ｃ３鎖式炭化水素基、又はシクロプロピルメチル基である化合物。
〔態様１３〕態様１２において、ｎが２である化合物。
〔態様１４〕本発明化合物において、Ａ２が窒素原子である化合物。
〔態様１５〕本発明化合物において、Ａ２がＣＨである化合物。
〔態様１６〕本発明化合物において、Ａ１がＮＣＨ３である化合物。
〔態様１７〕本発明化合物において、Ａ１がＮＣＨ３であり、Ａ２が窒素原子である化合物。
〔態様１８〕本発明化合物において、Ａ１が酸素原子又は硫黄原子である化合物。
〔態様１９〕本発明化合物において、Ａ１が酸素原子又は硫黄原子であり、Ａ２がＣＨである化合物。
〔態様２０〕本発明化合物において、Ａ１が酸素原子である化合物。
〔態様２１〕本発明化合物において、Ａ１が酸素原子であり、Ａ２がＣＨである化合物。
〔態様２２〕態様１～１３のいずれかにおいて、Ａ２が窒素原子である化合物。
〔態様２３〕態様１～１３のいずれかにおいて、Ａ２がＣＨである化合物。
〔態様２４〕態様１～１３のいずれかにおいて、Ａ１がＮＣＨ３である化合物。
〔態様２５〕態様１～１３のいずれかにおいて、Ａ１がＮＣＨ３であり、Ａ２が窒素原子である化合物。
〔態様２６〕態様１～１３のいずれかにおいて、Ａ１が酸素原子又は硫黄原子である化合物。
〔態様２７〕態様１～１３のいずれかにおいて、Ａ１が酸素原子又は硫黄原子であり、Ａ２がＣＨである化合物。
〔態様２８〕態様１～１３のいずれかにおいて、Ａ１が酸素原子である化合物。
〔態様２９〕態様１～１３のいずれかにおいて、Ａ１が酸素原子であり、Ａ２がＣＨである化合物。 [Aspect 1] The compound of the present invention, wherein n is 2.
[Aspect 2] In the compound of the present invention, R 2 may have a C2-C3 chain hydrocarbon group optionally having one or more halogen atoms, and one or more substituents selected from Group X A compound which is a good cyclopropyl group or a (cyclopropyl) methyl group which may have one or more substituents selected from group X.
[Aspect 3] The compound according to aspect 2, wherein n is 2.
[Aspect 4] The compound of the present invention, wherein R 2 is a C2-C3 chain hydrocarbon group, a cyclopropyl group or a cyclopropylmethyl group.
[Aspect 5] The compound according to Aspect 4, wherein n is 2.
[Aspect 6] The compound of the present invention, wherein R 1 is a trifluoromethyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group.
[Aspect 7] The compound according to Aspect 6, wherein n is 2.
[Aspect 8] In aspect 6, R 2 may have a C2-C3 chain hydrocarbon group optionally having one or more halogen atoms, and one or more substituents selected from group X A compound which is a cyclopropyl group or a (cyclopropyl group) methyl group which may have one or more substituents selected from group X;
[9] The compound according to aspect 8, wherein n is 2.
Aspect 10: A compound according to aspect 6, wherein R 2 is a C2-C3 chain hydrocarbon group or a cyclopropylmethyl group.
11. The compound according to aspect 10, wherein n is 2.
Embodiment 12: A compound according to Embodiment 6, wherein R 2 is an ethyl group, a C3 chain hydrocarbon group, or a cyclopropylmethyl group.
[13] The compound according to Aspect 12, wherein n is 2.
Aspect 14: A compound of the present invention wherein A 2 is a nitrogen atom.
Aspect 15: A compound of the present invention wherein A 2 is CH.
The compound of the present invention, wherein A 1 is NCH 3 .
[Aspect 17] The compound of the present invention, wherein A 1 is NCH 3 and A 2 is a nitrogen atom.
[Aspect 18] The compound of the present invention, wherein A 1 is an oxygen atom or a sulfur atom.
[Aspect 19] The compound of the present invention, wherein A 1 is an oxygen atom or a sulfur atom, and A 2 is CH.
[Aspect 20] The compound of the present invention, wherein A 1 is an oxygen atom.
[Aspect 21] The compound of the present invention, wherein A 1 is an oxygen atom and A 2 is CH.
[22] The compound wherein A 2 is a nitrogen atom in any of the modes 1 to 13.
Embodiment 23 The compound according to any of Embodiments 1 to 13, wherein A 2 is CH.
The compound of any one of aspects 1 to 13 wherein A 1 is NCH 3 .
Aspect 25. A compound according to any of aspects 1 to 13, wherein A 1 is NCH 3 and A 2 is a nitrogen atom.
Aspect 26. A compound according to any of aspects 1 to 13, wherein A 1 is an oxygen atom or a sulfur atom.
[Aspect 27] The compound according to any of Aspects 1 to 13, wherein A 1 is an oxygen atom or a sulfur atom, and A 2 is CH.
The compound of any one of aspects 1 to 13 wherein A 1 is an oxygen atom.
Aspect 29. A compound according to any of aspects 1 to 13, wherein A 1 is an oxygen atom and A 2 is CH.
　本発明化合物の製造中間体の実施態様としては、以下の化合物が挙げられる。 Examples of production intermediates of the compound of the present invention include the following compounds.
〔態様３０〕式（Ｘ）で示される化合物において、ＲｘがＯＲ２、フッ素原子又は塩素原子であり、
　Ｒ２が、１以上のハロゲン原子を有していてもよいＣ２－Ｃ５鎖式炭化水素基、１以上のハロゲン原子を有していてもよい（Ｃ１－Ｃ２アルコキシ）Ｃ１－Ｃ２アルキル基、群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル基、又は（群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル）Ｃ１－Ｃ２アルキル基であり、
　ｎが、０、１又は２であり、
　Ｒｙが、シアノ基、カルボキシ基、メトキシカルボニル基又はエトキシカルボニル基であり、
　群Ｘ：シアノ基及びハロゲン原子からなる群、
である化合物。
〔態様３１〕態様３０において、Ｒ２が１以上のハロゲン原子を有していてもよいＣ２－Ｃ４鎖式炭化水素基、群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル基、又は（群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル）メチル基である化合物。
〔態様３２〕態様３０において、Ｒ２が、Ｃ２－Ｃ４アルキル基、又はシクロプロピルメチル基である化合物。
〔態様３３〕態様３０において、ＲｘがＯＲ２であり、Ｒ２が、Ｃ２－Ｃ４アルキル基、又はシクロプロピルメチル基である化合物。
〔態様３４〕態様３０において、Ｒｘがフッ素原子又は塩素原子である化合物。
〔態様３５〕態様３０～３４のいずれか１つにおいて、Ｒｙがシアノ基である化合物。
〔態様３６〕態様３０～３４のいずれか１つにおいて、Ｒｙがカルボキシ基である化合物。
〔態様３７〕態様３０～３４のいずれか１つにおいて、Ｒｙがメトキシカルボニル基である化合物。
〔態様３８〕態様３０～３４のいずれか１つにおいて、Ｒｙがエトキシカルボニル基である化合物。
〔態様３９〕中間体Ｘにおいて、Ｒ２が１以上のハロゲン原子を有していてもよいＣ２－Ｃ４鎖式炭化水素基、群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル基、又は（群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル）メチル基である化合物。
〔態様４０〕中間体Ｘにおいて、Ｒ２が、Ｃ２－Ｃ４アルキル基、又はシクロプロピルメチル基である化合物。
〔態様４１〕中間体Ｘにおいて、ＲｘがＯＲ２であり、Ｒ２が、Ｃ２－Ｃ４アルキル基、又はシクロプロピルメチル基である化合物。
〔態様４２〕中間体Ｘにおいて、Ｒｘがフッ素原子又は塩素原子である化合物。
〔態様４３〕中間体Ｘ、態様３９～４２のいずれかにおいて、Ｒｙがカルボキシ基、メトキシカルボニル基又はエトキシカルボニル基である化合物。 [Aspect 30] In the compound represented by the formula (X), R x is OR 2 , a fluorine atom or a chlorine atom,
R 2 is a C 2 -C 5 chain hydrocarbon group which may have one or more halogen atoms, (C 1 -C 2 alkoxy) C 1 -C 2 alkyl group which may have one or more halogen atoms, a group A cyclopropyl group which may have one or more substituents selected from X, or (a cyclopropyl group optionally having one or more substituents selected from group X) C1-C2 alkyl group,
n is 0, 1 or 2;
R y is a cyano group, a carboxy group, a methoxycarbonyl group or an ethoxycarbonyl group,
Group X: a group consisting of a cyano group and a halogen atom,
A compound that is
[Aspect 31] In Aspect 30, R 2 is a C2-C4 chain hydrocarbon group optionally having one or more halogen atoms, and cyclo optionally having one or more substituents selected from Group X. A compound which is a propyl group or a (cyclopropyl) methyl group which may have one or more substituents selected from group X;
Embodiment 32. A compound according to embodiment 30, wherein R 2 is a C 2 -C 4 alkyl group or a cyclopropylmethyl group.
Aspect 33. A compound according to aspect 30, wherein R x is OR 2 and R 2 is a C2-C4 alkyl group or a cyclopropylmethyl group.
Aspect 34. A compound according to aspect 30, wherein R x is a fluorine atom or a chlorine atom.
Aspect 35. The compound according to any one of aspects 30 to 34, wherein R y is a cyano group.
Aspect 36. The compound according to any one of aspects 30 to 34, wherein R y is a carboxy group.
Aspect 37. The compound wherein R y is a methoxycarbonyl group in any one of aspects 30 to 34.
Aspect 38. A compound according to any one of aspects 30 to 34, wherein R y is an ethoxycarbonyl group.
[Aspect 39] In Intermediate X, R 2 may have a C2-C4 chain hydrocarbon group optionally having one or more halogen atoms, and one or more substituents selected from Group X A compound which is a cyclopropyl group or a (cyclopropyl group) methyl group which may have one or more substituents selected from group X;
Embodiment 40 A compound in which in the intermediate X, R 2 is a C2-C4 alkyl group or a cyclopropylmethyl group.
[41] The compound of Intermediate X, wherein R x is OR 2 and R 2 is a C2-C4 alkyl group or a cyclopropylmethyl group.
Embodiment 42 A compound in which in the intermediate X, R x is a fluorine atom or a chlorine atom.
Aspect 43. A compound according to any one of aspects 39 to 42, wherein R y is a carboxy group, a methoxycarbonyl group or an ethoxycarbonyl group.
　次に、本発明化合物の製造法について説明する。 Next, the process for producing the compound of the present invention is described.
製造法１
　式（Ｉ－ｃ）で示される化合物（以下、化合物（Ｉ－ｃ）と記す）は、式（Ｉ－ａ）で示される化合物（以下、化合物（Ｉ－ａ）と記す）又は式（Ｉ－ｂ）で示される化合物（以下、化合物（Ｉ－ｂ）と記す）を酸化することにより製造することができる。化合物（Ｉ－ｂ）は、化合物（Ｉ－ａ）を酸化することにより製造することができる。
Figure JPOXMLDOC01-appb-C000005
 ［式中、記号は前記と同じ意味を表す。］
　まず、化合物（Ｉ－ａ）から化合物（Ｉ－ｂ）を製造する方法について記載する。
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えばジクロロメタン、クロロホルム等のハロゲン化炭化水素（以下、ハロゲン化炭化水素類と記す）；アセトニトリル等のニトリル（以下、ニトリル類と記す）；メタノール、エタノール等のアルコール（以下、アルコール類と記す）；酢酸；水及びこれらの２種類以上の混合物が挙げられる。
　反応に用いられる酸化剤としては、例えば過ヨウ素酸ナトリウム、ｍ－クロロ過安息香酸（以下、ｍＣＰＢＡと記す）、及び過酸化水素が挙げられる。
　酸化剤として過酸化水素を用いる場合は、必要に応じて塩基又は触媒を加えてもよい。
　反応に用いられる塩基としては、炭酸ナトリウムが挙げられる。
　反応に用いられる触媒としては、例えばタングステン酸、及びタングステン酸ナトリウムが挙げられる。
　反応には、化合物（Ｉ－ａ）１モルに対して、酸化剤が通常１～１．２モルの割合で用いられる。
　反応に塩基が用いられる場合、化合物（Ｉ－ａ）１モルに対して、塩基が通常０．０１～１モルの割合で用いられる。
　反応に触媒が用いられる場合、化合物（Ｉ－ａ）１モルに対して、触媒が通常０．０１～０．５モルの割合で用いられる。
　反応温度は、通常－２０～８０℃の範囲である。反応時間は通常０．１～１２時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を必要に応じて還元剤（例えば亜硫酸ナトリウム、チオ硫酸ナトリウム）の水溶液、及び塩基（例えば炭酸水素ナトリウム）の水溶液で洗浄し、得られた有機層を乾燥、濃縮することにより、化合物（Ｉ－ｂ）を得ることができる。 Manufacturing method 1
The compound represented by the formula (Ic) (hereinafter referred to as the compound (Ic)) is a compound represented by the formula (Ia) (hereinafter referred to as the compound (Ia)) or the formula (Ic) It can manufacture by oxidizing the compound (It is hereafter described as a compound (Ib)) shown by -b). Compound (Ib) can be produced by oxidizing compound (Ia).
Figure JPOXMLDOC01-appb-C000005
 [Wherein, the symbols have the same meanings as described above. ]
First, a method for producing compound (Ib) from compound (Ia) is described.
The reaction is usually carried out in a solvent. Examples of the solvent used for the reaction include halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as halogenated hydrocarbons); nitriles such as acetonitrile (hereinafter referred to as nitriles); alcohols such as methanol and ethanol Hereinafter, it is described as an alcohol); acetic acid; water and a mixture of two or more of them.
Examples of the oxidizing agent used for the reaction include sodium periodate, m-chloroperbenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide.
When using hydrogen peroxide as an oxidizing agent, you may add a base or a catalyst as needed.
Sodium carbonate is mentioned as a base used for reaction.
As a catalyst used for reaction, tungstic acid and sodium tungstate are mentioned, for example.
In the reaction, the oxidizing agent is usually used in a proportion of 1 to 1.2 mol per 1 mol of the compound (Ia).
When a base is used in the reaction, the base is usually used in a proportion of 0.01 to 1 mole per 1 mole of the compound (Ia).
When a catalyst is used in the reaction, the catalyst is usually used in a proportion of 0.01 to 0.5 mol per 1 mol of compound (Ia).
The reaction temperature is usually in the range of -20 to 80 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, water is added to the reaction mixture, extraction is carried out with an organic solvent, and the organic layer is optionally treated with an aqueous solution of a reducing agent (eg sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (eg sodium hydrogencarbonate) The compound (Ib) can be obtained by washing and drying and concentration of the obtained organic layer.
　つぎに、化合物（Ｉ－ｂ）から化合物（Ｉ－ｃ）を製造する方法について記載する。
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えばハロゲン化炭化水素類、ニトリル類、アルコール類、酢酸、水及びこれらの２種類以上の混合物が挙げられる。
　反応に用いられる酸化剤としては、例えばｍＣＰＢＡ及び過酸化水素が挙げられる。
　酸化剤として過酸化水素を用いる場合は、必要に応じて塩基又は触媒を加えてもよい。
　反応に用いられる塩基としては、炭酸ナトリウムが挙げられる。
　反応に用いられる触媒としては、例えばタングステン酸ナトリウムが挙げられる。
　反応には、化合物（Ｉ－ｂ）１モルに対して、酸化剤が通常１～２モルの割合で用いられる。
　反応に塩基が用いられる場合、化合物（Ｉ－ｂ）１モルに対して、塩基が通常０．０１～１モルの割合で用いられる。
　反応に触媒が用いられる場合、化合物（Ｉ－ｂ）１モルに対して、触媒が通常０．０１～０．５モルの割合で用いられる。
　反応温度は、通常－２０～１２０℃の範囲である。反応時間は通常０．１～１２時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を必要に応じて還元剤（例えば亜硫酸ナトリウム、チオ硫酸ナトリウム）の水溶液、及び塩基（例えば炭酸水素ナトリウム）の水溶液で洗浄し、得られた有機層を乾燥、濃縮することにより、化合物（Ｉ－ｃ）を得ることができる。 Next, a method for producing compound (Ic) from compound (Ib) will be described.
The reaction is usually carried out in a solvent. As a solvent used for reaction, halogenated hydrocarbons, nitriles, alcohols, an acetic acid, water, and the mixture of 2 or more types of these are mentioned, for example.
Examples of the oxidizing agent used for the reaction include mCPBA and hydrogen peroxide.
When using hydrogen peroxide as an oxidizing agent, you may add a base or a catalyst as needed.
Sodium carbonate is mentioned as a base used for reaction.
As a catalyst used for reaction, sodium tungstate is mentioned, for example.
In the reaction, an oxidizing agent is usually used at a ratio of 1 to 2 moles relative to 1 mole of the compound (Ib).
When a base is used in the reaction, the base is usually used in a proportion of 0.01 to 1 mole per 1 mole of the compound (Ib).
When a catalyst is used in the reaction, the catalyst is usually used in a proportion of 0.01 to 0.5 mol per 1 mol of compound (Ib).
The reaction temperature is usually in the range of -20 to 120 ° C. The reaction time is usually in the range of 0.1 to 12 hours.
After completion of the reaction, water is added to the reaction mixture, extraction is carried out with an organic solvent, and the organic layer is optionally treated with an aqueous solution of a reducing agent (eg sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (eg sodium hydrogencarbonate) The compound (Ic) can be obtained by washing and drying and concentration of the obtained organic layer.
　また、化合物（Ｉ－ｃ）は、化合物（Ｉ－ａ）と酸化剤とを反応させることで、一段階反応（ワンポット）で製造することができる。
　反応は、酸化剤を化合物（Ｉ－ａ）１モルに対して通常２～５モルの割合で用い、化合物（Ｉ－ｂ）から化合物（Ｉ－ｃ）を製造する方法に準じて実施することができる。 In addition, compound (Ic) can be produced by a one-step reaction (one pot) by reacting compound (Ia) with an oxidizing agent.
The reaction is carried out according to the method for producing compound (Ic) from compound (Ib), using an oxidizing agent in a proportion of usually 2 to 5 moles relative to 1 mole of compound (Ia). Can.
製造法２
　本発明化合物は、式（Ｍ－１）で示される化合物（以下、化合物（Ｍ－１）と記す）と式（Ｒ－１）で示される化合物（以下、化合物（Ｒ－１）と記す）とを塩基の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000006
 ［式中、Ｘａは臭素原子又はヨウ素原子を表し、その他の記号は前記と同じ意味を表す。］
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えばテトラヒドロフラン（以下、ＴＨＦと記す）、１，４－ジオキサン、エチレングリコールジメチルエーテル（以下、ＤＭＥと記す）、メチルｔｅｒｔ－ブチルエーテル（以下、ＭＴＢＥと記す）等のエーテル（以下、エーテル類と記す）；トルエン、キシレン等の芳香族炭化水素（以下、芳香族炭化水素類と記す）；ジメチルホルムアミド（以下、ＤＭＦと記す）、Ｎ－メチルピロリドン等、ジメチルスルホキシド（以下、ＤＭＳＯと記す）等の非プロトン性極性溶媒（以下、非プロトン性極性溶媒類と記す）及びこれらの２種類以上の混合物が挙げられる。
　反応に用いられる塩基としては、例えばトリエチルアミン、ジイソピロピルエチルアミン、ピリジン、４－ジメチルアミノピリジン等の有機塩基（以下、有機塩基類と記す）；水素化ナトリウム等のアルカリ金属水素化物（以下、アルカリ金属水素化物類と記す）；炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩（以下、アルカリ金属炭酸塩類と記す）が挙げられる。
　反応には、化合物（Ｍ－１）１モルに対して、化合物（Ｒ－１）が通常１～１０モルの割合、塩基が通常１～５モルの割合で用いられる。
　反応温度は、通常－２０℃～１５０℃の範囲である。反応時間は通常０．５～２４時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより本発明化合物を得ることができる。
　化合物（Ｒ－１）は市販の化合物であるか、公知の方法に準じて製造することができる。 Manufacturing method 2
The compound of the present invention is a compound represented by the formula (M-1) (hereinafter referred to as a compound (M-1)) and a compound represented by the formula (R-1) (hereinafter referred to as a compound (R-1)) Can be produced by reacting in the presence of a base.
Figure JPOXMLDOC01-appb-C000006
 [Wherein, X a represents a bromine atom or an iodine atom, and the other symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Examples of the solvent used for the reaction include ethers such as tetrahydrofuran (hereinafter referred to as THF), 1,4-dioxane, ethylene glycol dimethyl ether (hereinafter referred to as DME), methyl tert-butyl ether (hereinafter referred to as MTBE) Hereinafter, referred to as ethers); aromatic hydrocarbons such as toluene and xylene (hereinafter referred to as aromatic hydrocarbons); dimethylformamide (hereinafter referred to as DMF), N-methylpyrrolidone and the like, dimethyl sulfoxide (hereinafter referred to as Aprotic polar solvents (hereinafter referred to as DMSO) and the like (hereinafter referred to as aprotic polar solvents) and mixtures of two or more of these can be mentioned.
Examples of the base used for the reaction include organic bases such as triethylamine, diisopyropylethylamine, pyridine and 4-dimethylaminopyridine (hereinafter referred to as organic bases); alkali metal hydrides such as sodium hydride (hereinafter referred to as Alkali metal hydrides); and alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates).
In the reaction, the compound (R-1) is used in a proportion of usually 1 to 10 mol, and the base is usually used in a proportion of 1 to 5 mol, per 1 mol of the compound (M-1).
The reaction temperature is usually in the range of -20 ° C to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, the compound of the present invention can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
The compound (R-1) is a commercially available compound or can be produced according to a known method.
製造法３
　式（Ｉ－２）で示される化合物（以下、化合物（Ｉ－２）と記す）は、式（Ｍ－２）で示される化合物（以下、化合物（Ｍ－２）と記す）と式（Ｒ－２）で示される化合物（以下、化合物（Ｒ－２）と記す）とを塩基の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000007
 ［式中、Ｘｂはフッ素原子又は塩素原子を表し、その他記号は前記と同じ意味を表す。］
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、エーテル類、芳香族炭化水素類、非プロトン性極性溶媒類、ハロゲン化炭化水素類、ニトリル類及びこれらの２種類以上の混合物が挙げられる。
　反応に用いられる塩基としては、例えばアルカリ金属水素化物類、有機塩基類、アルカリ金属炭酸塩類が挙げられる。
　反応には、化合物（Ｍ－２）１モルに対して、化合物（Ｒ－２）が通常１～１０モルの割合、塩基が通常１～５モルの割合で用いられる。
　反応温度は、通常－２０℃～１５０℃の範囲である。反応時間は通常０．５～２４時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物（Ｉ－２）を得ることができる。
　化合物（Ｒ－２）は市販の化合物であるか、公知の方法に準じて製造することができる。 Manufacturing method 3
The compound represented by formula (I-2) (hereinafter referred to as compound (I-2)) is a compound represented by formula (M-2) (hereinafter referred to as compound (M-2)) and the compound represented by formula (R-2) It can be produced by reacting the compound represented by -2) (hereinafter referred to as compound (R-2)) in the presence of a base.
Figure JPOXMLDOC01-appb-C000007
 [Wherein, X b represents a fluorine atom or a chlorine atom, and the other symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Examples of the solvent used for the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, nitriles and mixtures of two or more of these.
Examples of the base used for the reaction include alkali metal hydrides, organic bases and alkali metal carbonates.
In the reaction, the compound (R-2) is used in a proportion of usually 1 to 10 mol, and the base is usually used in a proportion of 1 to 5 mol, per 1 mol of the compound (M-2).
The reaction temperature is usually in the range of -20 ° C to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, water is added to the reaction mixture, extraction is performed with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration to give compound (I-2).
The compound (R-2) is a commercially available compound or can be produced according to a known method.
製造法４
　本発明化合物は、式（Ｍ－１１）で示される化合物（以下、化合物（Ｍ－１１）と記す）を分子内で縮合させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000008
 ［式中、記号は前記と同じ意味を表す。］
　反応に用いられる溶媒としては、エーテル類、芳香族炭化水素類、非プロトン性極性溶媒類、ハロゲン化炭化水素類、ニトリル類及びこれらの２種類以上の混合物が挙げられる。
　反応は、縮合剤、酸、塩基又は塩素化剤を用いることができる。
　縮合剤としては、無水酢酸；トリフルオロ酢酸無水物；１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩（以下、ＷＳＣと記す）；トリフェニルホスフィン、塩基及び四塩化炭素もしくは四臭化炭素の混合物；トリフェニルホスフィンとアゾジカルボン酸ジエチル等のアゾジエステル類との混合物等が挙げられる。
　酸としては、パラトルエンスルホン酸等のスルホン酸類、酢酸等のカルボン酸類及びポリリン酸等が挙げられる。
　塩基としては、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属水素化物類、リン酸三カリウム等が挙げられる。
　塩素化剤としては、オキシ塩化リン等が挙げられる。
　反応には、化合物（Ｍ－１１）１モルに対して、縮合剤を用いる場合には縮合剤が通常１～５モルの割合、酸を用いる場合には酸が通常０．１モル～５モルの割合、塩基を用いる場合には塩基が通常１モル～５モルの割合、塩素化剤を用いる場合には塩素化剤が通常１モル～５モルの割合で用いられる。
　反応温度は、通常０～２００℃の範囲である。反応時間は、通常０．１～２４時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより本発明化合物を得ることができる。 Manufacturing method 4
The compound of the present invention can be produced by intramolecular condensation of a compound represented by formula (M-11) (hereinafter referred to as compound (M-11)).
Figure JPOXMLDOC01-appb-C000008
 [Wherein, the symbols have the same meanings as described above. ]
Examples of the solvent used for the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, nitriles and mixtures of two or more of these.
The reaction can use a condensing agent, an acid, a base or a chlorinating agent.
As a condensing agent, acetic anhydride; trifluoroacetic anhydride; 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as WSC); triphenyl phosphine, base and carbon tetrachloride or tetra odor Mixtures of carbon trioxide and mixtures of triphenyl phosphine and azo diesters such as diethyl azodicarboxylate and the like can be mentioned.
Examples of the acid include sulfonic acids such as para-toluenesulfonic acid, carboxylic acids such as acetic acid, and polyphosphoric acid.
Examples of the base include organic bases, alkali metal carbonates, alkali metal hydrides, tripotassium phosphate and the like.
As the chlorinating agent, phosphorus oxychloride and the like can be mentioned.
When using a condensing agent, the proportion of the condensing agent is usually 1 to 5 mol, and when using an acid, the acid is usually 0.1 mol to 5 mol, relative to 1 mol of the compound (M-11). When a base is used, the base is usually used in a proportion of 1 mol to 5 mol. When a chlorinating agent is used, the chlorinating agent is usually used in a proportion of 1 mol to 5 mol.
The reaction temperature is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound of the present invention can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
製造法５
　式（Ｉ－４）で示される化合物（以下、化合物（Ｉ－４）と記す）は、式（Ｍ－２－ｏ）で示される化合物（以下、化合物（Ｍ－２－ｏ）と記す）と化合物（Ｒ－２）とを塩基の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000009
 ［式中、記号は前記と同じ意味を表す。］
　反応は、製造法３に準じて実施することができる。 Manufacturing method 5
The compound represented by the formula (I-4) (hereinafter referred to as the compound (I-4)) is a compound represented by the formula (M-2-o) (hereinafter referred to as the compound (M-2-o)) And compound (R-2) in the presence of a base.
Figure JPOXMLDOC01-appb-C000009
 [Wherein, the symbols have the same meanings as described above. ]
The reaction can be carried out according to production method 3.
参考製造法１
　化合物（Ｍ－１）は、式（Ｍ－３）で示される化合物（以下、化合物（Ｍ－３）と記す）とビス（ピナコラト）ジボロンとを塩基及び金属触媒の存在下で反応させて式（Ｍ－４）で示される化合物（以下、化合物（Ｍ－４）と記す）を得た後、化合物（Ｍ－４）を加水分解することにより製造することができる。
Figure JPOXMLDOC01-appb-C000010
 ［式中、記号は前記と同じ意味を表す。］
　これらの反応は、J. Am. Chem. Soc., 2009, 131, 8855に記載の方法に準じて実施することができる。 Reference manufacturing method 1
The compound (M-1) is prepared by reacting a compound represented by the formula (M-3) (hereinafter referred to as the compound (M-3)) with bis (pinacolato) diboron in the presence of a base and a metal catalyst. After obtaining the compound represented by (M-4) (hereinafter referred to as compound (M-4)), it can be produced by hydrolyzing compound (M-4).
Figure JPOXMLDOC01-appb-C000010
 [Wherein, the symbols have the same meanings as described above. ]
These reactions can be carried out according to the method described in J. Am. Chem. Soc., 2009, 131, 8855.

参考製造法２
　化合物（Ｍ－３－ａ）で示される化合物（以下、化合物（Ｍ－３－ａ）と記す）は、式（Ｍ－５）で示される化合物（以下、化合物（Ｍ－５）と記す）又は式（Ｍ－６）で示される化合物（以下、化合物（Ｍ－６）と記す）を酸化することにより製造することができる。化合物（Ｍ－６）は、化合物（Ｍ－５）を酸化することにより製造することができる。
Figure JPOXMLDOC01-appb-C000011
 ［式中、記号は前記と同じ意味を表す。］
　これらの反応は、製造法１に準じて実施することができる。
Reference manufacturing method 2
The compound represented by the compound (M-3-a) (hereinafter referred to as the compound (M-3-a)) is a compound represented by the formula (M-5) (hereinafter referred to as the compound (M-5)) Alternatively, it can be produced by oxidizing a compound represented by the formula (M-6) (hereinafter referred to as a compound (M-6)). Compound (M-6) can be produced by oxidizing compound (M-5).
Figure JPOXMLDOC01-appb-C000011
 [Wherein, the symbols have the same meanings as described above. ]
These reactions can be carried out according to production method 1.
参考製造法３
　化合物（Ｍ－５）は、式（Ｍ－７）で示される化合物（以下、化合物（Ｍ－７）と記す）とエタンチオールとを塩基の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000012
 ［式中、記号は前記と同じ意味を表す。］
　反応は、国際公開第2013/018928号に記載の方法に準じて実施することができる。 Reference manufacturing method 3
The compound (M-5) can be produced by reacting a compound represented by the formula (M-7) (hereinafter referred to as compound (M-7)) with ethanethiol in the presence of a base.
Figure JPOXMLDOC01-appb-C000012
 [Wherein, the symbols have the same meanings as described above. ]
The reaction can be carried out according to the method described in WO 2013/018928.
参考製造法４
　化合物（Ｍ－７）は、式（Ｍ－８）で示される化合物（以下、化合物（Ｍ－８）と記す）を分子内で縮合させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000013
 ［式中、記号は前記と同じ意味を表す。］
　反応は、国際公開第2013/018928号に記載の方法に準じて実施することができる。 Reference manufacturing method 4
Compound (M-7) can be produced by intramolecular condensation of a compound represented by formula (M-8) (hereinafter referred to as compound (M-8)).
Figure JPOXMLDOC01-appb-C000013
 [Wherein, the symbols have the same meanings as described above. ]
The reaction can be carried out according to the method described in WO 2013/018928.
参考製造法５
　化合物（Ｍ－８）は、式（Ｍ－９）で示される化合物（以下、化合物（Ｍ－９）と記す）と式（Ｍ－１０）で示される化合物（以下、化合物（Ｍ－１０）と記す）とを反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000014
 ［式中、記号は前記と同じ意味を表す。］
　反応は、国際公開第2013/018928号に記載の方法に準じて実施することができる。
　化合物（Ｍ－９）及び化合物（Ｍ－１０）は、市販の化合物であるか、又は公知の方法に準じて製造することができる。 Reference manufacturing method 5
The compound (M-8) is a compound represented by the formula (M-9) (hereinafter referred to as compound (M-9)) and a compound represented by the formula (M-10) (hereinafter referred to as the compound (M-10) Can be produced by reacting with
Figure JPOXMLDOC01-appb-C000014
 [Wherein, the symbols have the same meanings as described above. ]
The reaction can be carried out according to the method described in WO 2013/018928.
Compound (M-9) and compound (M-10) are commercially available compounds or can be produced according to known methods.
参考製造法６
　化合物（Ｍ－１）は、式（Ｉ－３）で示される化合物（以下、化合物（Ｉ－３）と記す）を酸の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000015
 ［式中、記号は前記と同じ意味を表す。］
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、エーテル類、芳香族炭化水素類、非プロトン性極性溶媒、ハロゲン化炭化水素類、ニトリル類、水及びこれらの２種類以上の混合物が挙げられる。
　反応に用いられる酸としては、例えばトリフルオロ酢酸、酢酸及び塩酸が挙げられる。
　反応には、化合物（Ｉ－３）１モルに対して、酸が通常１～２０モルの割合で用いられる。
　反応温度は、通常－２０℃～１５０℃の範囲である。反応時間は通常０．５～２４時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物（Ｍ－１）を得ることができる。 Reference manufacturing method 6
The compound (M-1) can be produced by reacting a compound represented by the formula (I-3) (hereinafter referred to as compound (I-3)) in the presence of an acid.
Figure JPOXMLDOC01-appb-C000015
 [Wherein, the symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Examples of the solvent used for the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, nitriles, water and a mixture of two or more of these.
Examples of the acid used for the reaction include trifluoroacetic acid, acetic acid and hydrochloric acid.
In the reaction, the acid is usually used in a ratio of 1 to 20 moles relative to 1 mole of the compound (I-3).
The reaction temperature is usually in the range of -20 ° C to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, water is added to the reaction mixture, extraction is performed with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration to give compound (M-1).
参考製造法７
　化合物（Ｍ－１１）は、化合物（Ｍ－９）と式（Ｍ－１２）で示される化合物（以下、化合物（Ｍ－１２）と記す）とを縮合剤の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000016
 ［式中、記号は前記と同じ意味を表す。］
　反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、エーテル類、芳香族炭化水素類、非プロトン性極性溶媒、ハロゲン化炭化水素類、ニトリル類、有機塩基類及びこれらの２種類以上の混合物が挙げられる。
　反応に用いられる縮合剤としては、例えばＷＳＣ、１，３－ジシクロヘキシルカルボジイミド等のカルボジイミド類が挙げられる。
　反応は、必要に応じて触媒を用いて行うこともできる。触媒としては、例えば１－ヒドロキシベンゾトリアゾールが挙げられる。反応に触媒を用いる場合、化合物（Ｍ－９）１モルに対して、触媒が通常０．０１～１モルの割合で用いられる。
　反応には、化合物（Ｍ－９）１モルに対して、化合物（Ｍ－１２）が通常０．５～２モルの割合、縮合剤が通常１～５モルの割合で用いられる。
　反応温度は、通常０～１２０℃の範囲である。反応時間は、通常０．１～２４時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物（Ｍ－１１）を得ることができる。 Reference manufacturing method 7
Compound (M-11) is produced by reacting compound (M-9) with a compound represented by formula (M-12) (hereinafter referred to as compound (M-12)) in the presence of a condensing agent can do.
Figure JPOXMLDOC01-appb-C000016
 [Wherein, the symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Examples of the solvent used for the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, nitriles, organic bases, and a mixture of two or more of these.
As a condensing agent used for reaction, carbodiimides, such as WSC and a 1, 3- dicyclohexyl carbodiimide, are mentioned, for example.
The reaction can also be carried out using a catalyst, if necessary. Examples of the catalyst include 1-hydroxybenzotriazole. When a catalyst is used in the reaction, the catalyst is usually used in a proportion of 0.01 to 1 mole per 1 mole of the compound (M-9).
In the reaction, the compound (M-12) is usually used in a proportion of 0.5 to 2 mol and the condensing agent is usually used in a proportion of 1 to 5 mol with respect to 1 mol of the compound (M-9).
The reaction temperature is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, water is added to the reaction mixture, extraction is performed with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration to give compound (M-11).
参考製造法８
　化合物（Ｍ－１２）は、式（Ｍ－１３）で示される化合物（以下、化合物（Ｍ－１３）と記す）又は式（Ｍ－１８）で示される化合物（以下、化合物（Ｍ－１８）と記す）を酸又は塩基を用いて加水分解することにより製造することができる。化合物（Ｍ－１８）は、化合物（Ｍ－１３）を酸又は塩基を用いて加溶媒分解することにより製造することができる。
Figure JPOXMLDOC01-appb-C000017
 ［式中、Ｒ３はメチル基又はエチル基を表し、その他記号は前記と同じ意味を表す。］
　まず、化合物（Ｍ－１３）から化合物（Ｍ－１２）を製造する方法について記載する。
　酸を用いて加水分解する場合、反応は通常酸の水溶液中で行われる。
　反応に用いられる酸としては、例えば塩酸、硝酸、硫酸等の鉱酸類が挙げられる。
　反応には、化合物（Ｍ－１３）１モルに対して、酸が通常１～５０モルの割合で用いられる。
　反応温度は、通常０～１００℃の範囲である。反応時間は通常０．１～２４時間の範囲である。
　反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ－１２）を単離することができる。 Reference manufacturing method 8
The compound (M-12) is a compound represented by the formula (M-13) (hereinafter referred to as a compound (M-13)) or a compound represented by the formula (M-18) (hereinafter referred to as a compound (M-18) Can be produced by hydrolysis using an acid or a base. Compound (M-18) can be produced by solvolysis of compound (M-13) with an acid or a base.
Figure JPOXMLDOC01-appb-C000017
 [Wherein, R 3 represents a methyl group or an ethyl group, and the other symbols have the same meanings as described above. ]
First, a method for producing a compound (M-12) from the compound (M-13) is described.
When hydrolysis is carried out using an acid, the reaction is usually carried out in an aqueous solution of the acid.
As an acid used for reaction, mineral acids, such as hydrochloric acid, nitric acid, a sulfuric acid, are mentioned, for example.
In the reaction, the acid is usually used in a proportion of 1 to 50 moles relative to 1 mole of the compound (M-13).
The reaction temperature is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture can be extracted with an organic solvent, and the organic layer can be subjected to post-treatment procedures such as drying and concentration to isolate the compound (M-12).
　塩基を用いて加水分解する場合、反応は通常溶媒中で行われる。反応に用いられる溶媒としては、例えばエーテル類、アルコール類、水及びこれらの２種類以上の混合物が挙げられる。
　反応に用いられる塩基としては、例えば水酸化ナトリウム、水酸化カリウム等のアルカリ金属水酸化物が挙げられる。
　反応には、化合物（Ｍ－１３）１モルに対して、塩基が通常１～１０モルの割合で用いられる。
　反応温度は、通常０～１２０℃の範囲である。反応時間は通常０．１～２４時間の範囲である。
　反応終了後は、反応混合物に塩酸等の酸を加えて酸性にした後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ－１２）を単離することができる。 When hydrolysis is carried out using a base, the reaction is usually carried out in a solvent. As a solvent used for reaction, ether, alcohol, water, and the mixture of 2 or more types of these are mentioned, for example.
Examples of the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
In the reaction, the base is usually used in a proportion of 1 to 10 moles relative to 1 mole of the compound (M-13).
The reaction temperature is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is acidified with an acid such as hydrochloric acid, and extracted with an organic solvent, followed by drying and concentration of the organic layer, etc. It can be isolated.
　つぎに、化合物（Ｍ－１８）から化合物（Ｍ－１２）を製造する方法について記載する。
　酸を用いて加水分解する場合、反応は通常酸の水溶液中で行われる。
　反応に用いられる酸としては、例えば塩酸、硝酸、硫酸等の鉱酸類が挙げられる。
　反応には、化合物（Ｍ－１８）１モルに対して、酸が通常１～５０モルの割合で用いられる。
　反応温度は、通常０～１００℃の範囲である。反応時間は通常０．１～２４時間の範囲である。
　反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ－１２）を単離することができる。 Next, a method for producing a compound (M-12) from the compound (M-18) is described.
When hydrolysis is carried out using an acid, the reaction is usually carried out in an aqueous solution of the acid.
As an acid used for reaction, mineral acids, such as hydrochloric acid, nitric acid, a sulfuric acid, are mentioned, for example.
In the reaction, the acid is usually used in a proportion of 1 to 50 moles relative to 1 mole of the compound (M-18).
The reaction temperature is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture can be extracted with an organic solvent, and the organic layer can be subjected to post-treatment procedures such as drying and concentration to isolate the compound (M-12).
　塩基を用いて加水分解する場合、反応は通常溶媒中で行われる。反応に用いられる溶媒としては、例えばエーテル類、アルコール類、水及びこれらの２種類以上の混合物が挙げられる。
　反応に用いられる塩基としては、例えば水酸化ナトリウム、水酸化カリウム等のアルカリ金属水酸化物が挙げられる。
　反応には、化合物（Ｍ－１８）１モルに対して、塩基が通常１～１０モルの割合で用いられる。
　反応温度は、通常０～１２０℃の範囲である。反応時間は通常０．１～２４時間の範囲である。
　反応終了後は、反応混合物に塩酸等の酸を加えて酸性にした後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ－１２）を単離することができる。 When hydrolysis is carried out using a base, the reaction is usually carried out in a solvent. As a solvent used for reaction, ether, alcohol, water, and the mixture of 2 or more types of these are mentioned, for example.
Examples of the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
In the reaction, the base is usually used in a proportion of 1 to 10 moles relative to 1 mole of the compound (M-18).
The reaction temperature is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is acidified with an acid such as hydrochloric acid, and extracted with an organic solvent, followed by drying and concentration of the organic layer, etc. It can be isolated.
　つぎに、化合物（Ｍ－１３）から化合物（Ｍ－１８）を製造する方法について記載する。
　酸を用いて加溶媒分解する場合、反応は通常溶媒中で行われる。
　反応に用いられる溶媒は、Ｒ３がメチル基であればメタノールであり、Ｒ３がエチル基であればエタノールである。
　反応に用いられる酸としては、例えば塩酸、硝酸、硫酸等の鉱酸類が挙げられる。
　反応には、化合物（Ｍ－１３）１モルに対して、酸が通常１～５０モルの割合で用いられる。
　反応温度は、通常０～１００℃の範囲である。反応時間は通常０．１～２４時間の範囲である。
　反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ－１８）を単離することができる。 Next, a method for producing a compound (M-18) from the compound (M-13) is described.
In the case of solvolysis using an acid, the reaction is usually carried out in a solvent.
The solvent used for the reaction is methanol if R 3 is a methyl group and ethanol if R 3 is an ethyl group.
As an acid used for reaction, mineral acids, such as hydrochloric acid, nitric acid, a sulfuric acid, are mentioned, for example.
In the reaction, the acid is usually used in a proportion of 1 to 50 moles relative to 1 mole of the compound (M-13).
The reaction temperature is usually in the range of 0 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture can be extracted with an organic solvent, and the organic layer can be subjected to post-treatment procedures such as drying and concentration to isolate the compound (M-18).
　塩基を用いて加溶媒分解する場合、反応は通常溶媒中で行われる。
　反応に用いられる溶媒は、Ｒ３がメチル基であればメタノールであり、Ｒ３がエチル基であればエタノールである。
　反応に用いられる塩基としては、例えば水酸化ナトリウム、水酸化カリウム等のアルカリ金属水酸化物が挙げられる。
　反応には、化合物（Ｍ－１３）１モルに対して、塩基が通常１～１０モルの割合で用いられる。
　反応温度は、通常０～１２０℃の範囲である。反応時間は通常０．１～２４時間の範囲である。
　反応終了後は、反応混合物に塩酸等の酸を加えて酸性にした後、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（Ｍ－１８）を単離することができる。 In the case of solvolysis using a base, the reaction is usually carried out in a solvent.
The solvent used for the reaction is methanol if R 3 is a methyl group and ethanol if R 3 is an ethyl group.
Examples of the base used for the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
In the reaction, the base is usually used in a proportion of 1 to 10 moles relative to 1 mole of the compound (M-13).
The reaction temperature is usually in the range of 0 to 120 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the reaction mixture is acidified with an acid such as hydrochloric acid and extracted with an organic solvent, and the organic layer is dried and concentrated to give a compound (M-18). It can be isolated.
参考製造法９
　化合物（Ｍ－１３－ｃ）で示される化合物（以下、化合物（Ｍ－１３－ｃ）と記す）は、式（Ｍ－１３－ａ）で示される化合物（以下、化合物（Ｍ－１３－ａ）と記す）又は式（Ｍ－１３－ｂ）で示される化合物（以下、化合物（Ｍ－１３－ｂ）と記す）を酸化することにより製造することができる。化合物（Ｍ－１３－ｂ）は、化合物（Ｍ－１３－ａ）を酸化することにより製造することができる。
Figure JPOXMLDOC01-appb-C000018
 ［式中、記号は前記と同じ意味を表す。］
　これらの反応は、製造法１に準じて実施することができる。 Reference manufacturing method 9
The compound represented by the compound (M-13-c) (hereinafter referred to as the compound (M-13-c)) is a compound represented by the formula (M-13-a) (hereinafter referred to as the compound (M-13-a) Or a compound represented by the formula (M-13-b) (hereinafter referred to as a compound (M-13-b)). Compound (M-13-b) can be produced by oxidizing compound (M-13-a).
Figure JPOXMLDOC01-appb-C000018
 [Wherein, the symbols have the same meanings as described above. ]
These reactions can be carried out according to production method 1.
参考製造法１０
　化合物（Ｍ－１３－ａ）は、式（Ｍ－１４）で示される化合物（以下、化合物（Ｍ－１４）と記す）と化合物（Ｒ－２）とを塩基の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000019
 ［式中、記号は前記と同じ意味を表す。］
　反応は、製造法３に準じて実施することができる。 Reference manufacturing method 10
The compound (M-13-a) can be produced by reacting a compound represented by the formula (M-14) (hereinafter referred to as compound (M-14)) with a compound (R-2) in the presence of a base It can be manufactured.
Figure JPOXMLDOC01-appb-C000019
 [Wherein, the symbols have the same meanings as described above. ]
The reaction can be carried out according to production method 3.
参考製造法１１
　式（Ｍ－１４－ａ）で示される化合物（以下、化合物（Ｍ－１４－ａ）と記す）は、式（Ｍ－１５）で示される化合物（以下、化合物（Ｍ－１５）と記す）とエタンチオールとを塩基の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000020
 ［式中、記号は前記と同じ意味を表す。］
　反応は通常溶媒中で行われる。反応に用いられる溶媒としては、例えばエーテル類、芳香族炭化水素類、ニトリル類、非プロトン性極性溶媒及びこれらの２種類以上の混合物が挙げられる。
　反応に用いられる塩基としては、例えばアルカリ金属炭酸塩類及びアルカリ金属水素化物類が挙げられる。
　反応には、化合物（Ｍ－１５）１モルに対して、エタンチオールが通常１～１０モルの割合、塩基が通常１～１０モルの割合で用いられる。
　反応温度は、通常０～１５０℃の範囲である。反応時間は通常０．５～２４時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物（Ｍ－１４－ａ）を得ることができる。
　化合物（Ｍ－１５）は、市販の化合物であるか、又は公知の方法に準じて製造することができる。 Reference manufacturing method 11
The compound represented by the formula (M-14-a) (hereinafter referred to as a compound (M-14-a)) is a compound represented by the formula (M-15) (hereinafter referred to as a compound (M-15)) And ethanethiol in the presence of a base.
Figure JPOXMLDOC01-appb-C000020
 [Wherein, the symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Examples of the solvent used for the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents and mixtures of two or more of these.
As a base used for reaction, an alkali metal carbonate and alkali metal hydrides are mentioned, for example.
In the reaction, ethanethiol is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol, per 1 mol of compound (M-15).
The reaction temperature is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, water is added to the reaction mixture, extraction is performed with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration to give compound (M-14-a).
Compound (M-15) is a commercially available compound or can be produced according to a known method.
参考製造法１２
　化合物（Ｍ－１４）は、式（Ｍ－１６）で示される化合物（以下、化合物（Ｍ－１６）と記す）を脱水することにより製造することができる。
Figure JPOXMLDOC01-appb-C000021
 ［式中、記号は前記と同じ意味を表す。］
　反応は通常溶媒中で行われる。反応に用いられる溶媒としては、例えばエーテル類、芳香族炭化水素類、ニトリル類、非プロトン性極性溶媒及びこれらの２種類以上の混合物が挙げられる。
　反応に用いられる脱水剤としては、例えば塩化チオニル、オキシ塩化リン及びトリフルオロメタンスルホン酸が挙げられる。
　反応には、化合物（Ｍ－１６）１モルに対して、脱水剤が通常１～１０モルの割合で用いられる。
　反応温度は、通常０～１５０℃の範囲である。反応時間は通常０．５～２４時間の範囲である。
　反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物（Ｍ－１４）を得ることができる。 Reference manufacturing method 12
Compound (M-14) can be produced by dehydrating a compound represented by formula (M-16) (hereinafter referred to as compound (M-16)).
Figure JPOXMLDOC01-appb-C000021
 [Wherein, the symbols have the same meanings as described above. ]
The reaction is usually carried out in a solvent. Examples of the solvent used for the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents and mixtures of two or more of these.
Examples of the dehydrating agent used for the reaction include thionyl chloride, phosphorus oxychloride and trifluoromethanesulfonic acid.
In the reaction, a dehydrating agent is usually used in a proportion of 1 to 10 moles relative to 1 mole of the compound (M-16).
The reaction temperature is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.5 to 24 hours.
After completion of the reaction, water is added to the reaction mixture, extraction is performed with an organic solvent, and the organic layer is subjected to post-treatment operations such as drying and concentration to give compound (M-14).
参考製造法１３
　化合物（Ｍ－１６）は、式（Ｍ－１７）で示される化合物（以下、化合物（Ｍ－１７）と記す）とエタンチオールとを塩基の存在下で反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-C000022
 ［式中、Ｘｃはフッ素原子又は塩素原子を表し、その他の記号は前記と同じ意味を表す。］
　反応は、参考製造法１１に記載の方法に準じて実施することができる。
　化合物（Ｍ－１７）は、市販の化合物であるか、又は公知の方法に準じて製造することができる。 Reference manufacturing method 13
Compound (M-16) can be produced by reacting a compound represented by formula (M-17) (hereinafter referred to as compound (M-17)) with ethanethiol in the presence of a base.
Figure JPOXMLDOC01-appb-C000022
 [Wherein, X c represents a fluorine atom or a chlorine atom, and the other symbols have the same meanings as described above. ]
The reaction can be carried out according to the method described in Reference Production Method 11.
Compound (M-17) is a commercially available compound or can be produced according to a known method.
参考製造法１４
　化合物（Ｍ－２－ｏ）は、化合物（Ｍ－３－ａ）を酸化することにより製造することができる。
Figure JPOXMLDOC01-appb-C000023
 ［式中、記号は前記と同じ意味を表す。］
　反応は、国際公開第2013/018928号に記載の方法に準じて実施することができる。 Reference manufacturing method 14
Compound (M-2-o) can be produced by oxidizing compound (M-3-a).
Figure JPOXMLDOC01-appb-C000023
 [Wherein, the symbols have the same meanings as described above. ]
The reaction can be carried out according to the method described in WO 2013/018928.
　次に、本発明化合物の具体例を以下に示す。これらの化合物は本明細書の実施例、製造法及び参考製造法に準じて製造することができる。 Next, specific examples of the compound of the present invention are shown below. These compounds can be produced according to the examples, production methods and reference production methods of the present specification.
　式（Ｌ－１）：
Figure JPOXMLDOC01-appb-C000024
 で示される化合物において、Ａ1がＮＣＨ３であり、Ａ2が窒素原子であり、Ｒ2が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX1と記す）。 Formula (L-1):
Figure JPOXMLDOC01-appb-C000024
 Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds Marked as group SX1).
Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000025
　式（Ｌ－１）で示される化合物において、Ａ１が酸素原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX2と記す）。
　式（Ｌ－１）で示される化合物において、Ａ１が硫黄原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX3と記す）。
　式（Ｌ－１）で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX4と記す）。
　式（Ｌ－１）で示される化合物において、Ａ１が酸素原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX5と記す）。
　式（Ｌ－１）で示される化合物において、Ａ１が硫黄原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX6と記す）。 In the compound represented by the formula (L-1), A 1 is an oxygen atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3]. A certain compound (hereinafter referred to as compound group SX2).
In the compound represented by the formula (L-1), A 1 is a sulfur atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3]. A certain compound (hereinafter referred to as compound group SX3).
In the compound represented by the formula (L-1), A 1 is NCH 3 , A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX4).
In the compound represented by the formula (L-1), A 1 is an oxygen atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound (hereinafter referred to as compound group SX5).
In the compound represented by the formula (L-1), A 1 is a sulfur atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX6).
　式（Ｌ－２）：
Figure JPOXMLDOC01-appb-C000026
 で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX7と記す）。
　式（Ｌ－２）で示される化合物において、Ａ１が酸素原子であり、Ａ２が窒素原子であり、Ｒ２2が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX8と記す）。
　式（Ｌ－２）で示される化合物において、Ａ１が硫黄原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX9と記す）。
　式（Ｌ－２）で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX10と記す）。
　式（Ｌ－２）で示される化合物において、Ａ１が酸素原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX11と記す）。
　式（Ｌ－２）で示される化合物において、Ａ１が硫黄原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX12と記す）。 Formula (L-2):
Figure JPOXMLDOC01-appb-C000026
 Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds Marked as group SX7).
In the compound represented by the formula (L-2), A 1 is an oxygen atom, A 2 is nitrogen atom, R2 2 is in one of the substituents described in Table 1] - [Table 3] A certain compound (hereinafter referred to as compound group SX8).
In the compound represented by the formula (L-2), A 1 is a sulfur atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3]. A certain compound (hereinafter referred to as compound group SX9).
In the compound represented by the formula (L-2), A 1 is NCH 3 , A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX10).
In the compound represented by the formula (L-2), A 1 is an oxygen atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound (hereinafter referred to as compound group SX11).
In the compound represented by the formula (L-2), A 1 is a sulfur atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX12).
　式（Ｌ－３）：
Figure JPOXMLDOC01-appb-C000027
 で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX13と記す）。
　式（Ｌ－３）で示される化合物において、Ａ１が酸素原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX14と記す）。
　式（Ｌ－３）で示される化合物において、Ａ１が硫黄原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX15と記す）。
　式（Ｌ－３）で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２2がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX16と記す）。
　式（Ｌ－３）で示される化合物において、Ａ１が酸素原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX17と記す）。
　式（Ｌ－３）で示される化合物において、Ａ１が硫黄原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX18と記す）。 Formula (L-3):
Figure JPOXMLDOC01-appb-C000027
 Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds It describes as group SX13).
In the compound represented by the formula (L-3), A 1 is an oxygen atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3]. A certain compound (hereinafter referred to as compound group SX14).
In the compound represented by Formula (L-3), A 1 is a sulfur atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3]. A certain compound (hereinafter referred to as compound group SX15).
In the compound represented by the formula (L-3), A 1 is NCH 3, an A2 2 is CH, R 2 is, is any substituent as defined in Table 1] - [Table 3] Compound (hereinafter, referred to as compound group SX16).
In the compound represented by the formula (L-3), A 1 is an oxygen atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound (hereinafter, referred to as compound group SX17).
In the compound represented by the formula (L-3), A 1 is a sulfur atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter, referred to as compound group SX18).
　式（Ｌ－４）：
Figure JPOXMLDOC01-appb-C000028
 で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX19と記す）。
　式（Ｌ－４）で示される化合物において、Ａ１が酸素原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX20と記す）。
　式（Ｌ－４）で示される化合物において、Ａ１が硫黄原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX21と記す）。
　式（Ｌ－４）で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX22と記す）。
　式（Ｌ－４）で示される化合物において、Ａ１が酸素原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX23と記す）。
　式（Ｌ－４）で示される化合物において、Ａ１が硫黄原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX24と記す）。 Formula (L-4):
Figure JPOXMLDOC01-appb-C000028
 Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds It describes as group SX19).
In the compound represented by the formula (L-4), A 1 is an oxygen atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3]. A certain compound (hereinafter referred to as compound group SX20).
In the compound represented by the formula (L-4), A 1 is a sulfur atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3]. A certain compound (hereinafter referred to as compound group SX21).
In the compound represented by the formula (L-4), A 1 is NCH 3 , A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX22).
In the compound represented by the formula (L-4), A 1 is an oxygen atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound (hereinafter, referred to as compound group SX23).
In the compound represented by the formula (L-4), A 1 is a sulfur atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter, referred to as compound group SX24).
　式（Ｌ－５）：
Figure JPOXMLDOC01-appb-C000029
 で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX25と記す）。
　式（Ｌ－５）で示される化合物において、Ａ１が酸素原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX26と記す）。
　式（Ｌ－５）で示される化合物において、Ａ1が硫黄原子であり、Ａ2が窒素原子であり、Ｒ2が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX27と記す）。
　式（Ｌ－５）で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX28と記す）。
　式（Ｌ－５）で示される化合物において、Ａ１が酸素原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX29と記す）。
　式（Ｌ－５）で示される化合物において、Ａ１が硫黄原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX30と記す）。 Formula (L-5):
Figure JPOXMLDOC01-appb-C000029
 Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds Marked as group SX 25).
In the compound represented by the formula (L-5), A 1 is an oxygen atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3]. A certain compound (hereinafter referred to as compound group SX26).
In the compound represented by the formula (L-5), A 1 is a sulfur atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] A certain compound (hereinafter referred to as compound group SX27).
In the compound represented by the formula (L-5), A 1 is NCH 3 , A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX28).
In the compound represented by the formula (L-5), A 1 is an oxygen atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound (hereinafter referred to as compound group SX29).
In the compound represented by the formula (L-5), A 1 is a sulfur atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX30).
　式（Ｌ－６）：
Figure JPOXMLDOC01-appb-C000030
 で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX31と記す）。
　式（Ｌ－６）で示される化合物において、Ａ１が酸素原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX32と記す）。
　式（Ｌ－６）で示される化合物において、Ａ１が硫黄原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX33と記す）。
　式（Ｌ－６）で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX34と記す）。
　式（Ｌ－６）で示される化合物において、Ａ１が酸素原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX35と記す）。
　式（Ｌ－６）で示される化合物において、Ａ１が硫黄原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX36と記す）。 Formula (L-6):
Figure JPOXMLDOC01-appb-C000030
 Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds It describes as group SX31).
In the compound represented by the formula (L-6), A 1 is an oxygen atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3]. A certain compound (hereinafter referred to as compound group SX32).
In the compound represented by the formula (L-6), A 1 is a sulfur atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] A certain compound (hereinafter referred to as compound group SX33).
In the compound represented by the formula (L-6), A 1 is NCH 3 , A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX34).
In the compound represented by the formula (L-6), A 1 is an oxygen atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound (hereinafter, referred to as compound group SX35).
In the compound represented by Formula (L-6), A 1 is a sulfur atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound (hereinafter referred to as compound group SX36).
　式（Ｌ－７）：
Figure JPOXMLDOC01-appb-C000031
 で示される化合物において、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX37と記す）。 Formula (L-7):
Figure JPOXMLDOC01-appb-C000031
 In the compounds shown by the above, compounds in which R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compound group SX37).
　式（Ｌ－８）：
Figure JPOXMLDOC01-appb-C000032
 で示される化合物において、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX38と記す）。 Formula (L-8):
Figure JPOXMLDOC01-appb-C000032
 In the compounds shown by the above, compounds in which R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compound group SX38).
　式（Ｌ－９）：
Figure JPOXMLDOC01-appb-C000033
 で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX39と記す）。
　式（Ｌ－９）で示される化合物において、Ａ１が酸素原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX40と記す）。
　式（Ｌ－９）で示される化合物において、Ａ１が硫黄原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX41と記す）。
　式（Ｌ－９）で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX42と記す）。
　式（Ｌ－９）で示される化合物において、Ａ１が酸素原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX43と記す）。
　式（Ｌ－９）で示される化合物において、Ａ１が硫黄原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX44と記す）。 Formula (L-9):
Figure JPOXMLDOC01-appb-C000033
 Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds Marked as group SX39).
In the compound represented by the formula (L-9), A 1 is an oxygen atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3]. A certain compound (hereinafter referred to as compound group SX40).
In the compound represented by the formula (L-9), A 1 is a sulfur atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] A certain compound (hereinafter referred to as compound group SX41).
In the compound represented by the formula (L-9), A 1 is NCH 3 , A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX42).
In the compound represented by the formula (L-9), A 1 is an oxygen atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound (hereinafter referred to as compound group SX43).
In the compound represented by the formula (L-9), A 1 is a sulfur atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX44).
　式（Ｌ－１０）：
Figure JPOXMLDOC01-appb-C000034
 で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX45と記す）。
　式（Ｌ－１０）で示される化合物において、Ａ１が酸素原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX46と記す）。
　式（Ｌ－１０）で示される化合物において、Ａ１が硫黄原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX47と記す）。
　式（Ｌ－１０）で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX48と記す）。
　式（Ｌ－１０）で示される化合物において、Ａ１が酸素原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX49と記す）。
　式（Ｌ－１０）で示される化合物において、Ａ１1が硫黄原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX50と記す）。 Formula (L-10):
Figure JPOXMLDOC01-appb-C000034
 Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds It describes as group SX45).
In the compound represented by the formula (L-10), A 1 is an oxygen atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3]. A certain compound (hereinafter referred to as compound group SX46).
In the compound represented by the formula (L-10), A 1 is a sulfur atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] A certain compound (hereinafter referred to as compound group SX47).
In the compound represented by the formula (L-10), A 1 is NCH 3 , A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter, referred to as compound group SX48).
In the compound represented by the formula (L-10), A 1 is an oxygen atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound (hereinafter, referred to as compound group SX49).
In the compound represented by the formula (L-10), A1 1 is a sulfur atom, an A 2 is CH, R 2 is, is any substituent as defined in Table 1] - [Table 3] Compound (hereinafter, referred to as compound group SX50).
　式（Ｌ－１１）：
Figure JPOXMLDOC01-appb-C000035
 で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX51と記す）。
　式（Ｌ－１１）で示される化合物において、Ａ１が酸素原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX52と記す）。
　式（Ｌ－１１）で示される化合物において、Ａ１が硫黄原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX53と記す）。
　式（Ｌ－１１）で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX54と記す）。
　式（Ｌ－１１）で示される化合物において、Ａ１が酸素原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX55と記す）。
　式（Ｌ－１１）で示される化合物において、Ａ１が硫黄原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX56と記す）。 Formula (L-11):
Figure JPOXMLDOC01-appb-C000035
 Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds It describes as group SX51).
In the compound represented by the formula (L-11), A 1 is an oxygen atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3]. A certain compound (hereinafter referred to as compound group SX52).
In the compound represented by the formula (L-11), A 1 is a sulfur atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] A certain compound (hereinafter referred to as compound group SX53).
In the compound represented by the formula (L-11), A 1 is NCH 3 , A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter, referred to as compound group SX54).
In the compound represented by the formula (L-11), A 1 is an oxygen atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound (hereinafter referred to as compound group SX55).
In the compound represented by the formula (L-11), A 1 is a sulfur atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX56).
　式（Ｌ－１２）：
Figure JPOXMLDOC01-appb-C000036
 で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX57と記す）。
　式（Ｌ－１２）で示される化合物において、Ａ１が酸素原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX58と記す）。
　式（Ｌ－１２）で示される化合物において、Ａ１が硫黄原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX59と記す）。
　式（Ｌ－１２）で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX60と記す）。
　式（Ｌ－１２）で示される化合物において、Ａ１が酸素原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX61と記す）。
　式（Ｌ－１２）で示される化合物において、Ａ１が硫黄原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX62と記す）。 Formula (L-12):
Figure JPOXMLDOC01-appb-C000036
 Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds It describes as group SX57).
In the compound represented by the formula (L-12), A 1 is an oxygen atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3]. A certain compound (hereinafter referred to as compound group SX58).
In the compound represented by the formula (L-12), A 1 is a sulfur atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] A certain compound (hereinafter referred to as compound group SX59).
In the compound represented by the formula (L-12), A 1 is NCH 3 , A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX60).
In the compound represented by the formula (L-12), A 1 is an oxygen atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound (hereinafter referred to as compound group SX61).
In the compound represented by the formula (L-12), A 1 is a sulfur atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX62).
　式（Ｌ－１３）：
Figure JPOXMLDOC01-appb-C000037
 で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX63と記す）。
　式（Ｌ－１３）で示される化合物において、Ａ１が酸素原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX64と記す）。
　式（Ｌ－１３）で示される化合物において、Ａ１が硫黄原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX65と記す）。
　式（Ｌ－１３）で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX66と記す）。
　式（Ｌ－１３）で示される化合物において、Ａ１が酸素原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX67と記す）。
　式（Ｌ－１３）で示される化合物において、Ａ１が硫黄原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX68と記す）。 Formula (L-13):
Figure JPOXMLDOC01-appb-C000037
 Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds Marked as group SX63).
In the compound represented by the formula (L-13), A 1 is an oxygen atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] A certain compound (hereinafter referred to as compound group SX64).
In the compound represented by the formula (L-13), A 1 is a sulfur atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] A certain compound (hereinafter referred to as compound group SX65).
In the compound represented by the formula (L-13), A 1 is NCH 3 , A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX66).
In the compound represented by the formula (L-13), A 1 is an oxygen atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound (hereinafter referred to as compound group SX67).
In the compound represented by the formula (L-13), A 1 is a sulfur atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX68).
　式（Ｌ－１４）：
Figure JPOXMLDOC01-appb-C000038
 で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX69と記す）。
　式（Ｌ－１４）で示される化合物において、Ａ１が酸素原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX70と記す）。
　式（Ｌ－１４）で示される化合物において、Ａ１が硫黄原子であり、Ａ２が窒素原子であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX71と記す）。
　式（Ｌ－１４）で示される化合物において、Ａ１がＮＣＨ３であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX72と記す）。
　式（Ｌ－１４）で示される化合物において、Ａ１が酸素原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX73と記す）。
　式（Ｌ－１４）で示される化合物において、Ａ１が硫黄原子であり、Ａ２がＣＨであり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物（以下、化合物群SX74と記す）。 Formula (L-14):
Figure JPOXMLDOC01-appb-C000038
 Compounds in which A 1 is NCH 3 , A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] (hereinafter referred to as compounds Marked as group SX69).
In the compound represented by formula (L-14), A 1 is an oxygen atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3]. A certain compound (hereinafter referred to as compound group SX70).
In the compound represented by the formula (L-14), A 1 is a sulfur atom, A 2 is a nitrogen atom, and R 2 is any of the substituents described in [Table 1] to [Table 3] A certain compound (hereinafter referred to as compound group SX71).
In the compound represented by the formula (L-14), A 1 is NCH 3 , A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX72).
In the compound represented by the formula (L-14), A 1 is an oxygen atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound (hereinafter referred to as compound group SX73).
In the compound represented by the formula (L-14), A 1 is a sulfur atom, A 2 is CH, and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound (hereinafter referred to as compound group SX74).
　式（Ｌ－１５）：
Figure JPOXMLDOC01-appb-C000039
 で示される化合物において、Ｒｙがシアノ基であり、ｎが０であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物。
　式（Ｌ－１５）で示される化合物において、Ｒｙがシアノ基であり、ｎが１であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物。
　式（Ｌ－１５）で示される化合物において、Ｒｙがシアノ基であり、ｎが２であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物。
　式（Ｌ－１５）で示される化合物において、Ｒｙがカルボキシ基であり、ｎが０であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物。
　式（Ｌ－１５）で示される化合物において、Ｒｙがカルボキシ基であり、ｎが１であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物。
　式（Ｌ－１５）で示される化合物において、Ｒｙがカルボキシ基であり、ｎが２であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物。
　式（Ｌ－１５）で示される化合物において、Ｒｙがメトキシカルボニル基であり、ｎが０であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物。
　式（Ｌ－１５）で示される化合物において、Ｒｙがメトキシカルボニル基であり、ｎが１であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物。
　式（Ｌ－１５）で示される化合物において、Ｒｙがメトキシカルボニル基であり、ｎが２であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物。
　式（Ｌ－１５）で示される化合物において、Ｒｙがエトキシカルボニル基であり、ｎが０であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物。
　式（Ｌ－１５）で示される化合物において、Ｒｙがエトキシカルボニル基であり、ｎが１であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物。
　式（Ｌ－１５）で示される化合物において、Ｒｙがエトキシカルボニル基であり、ｎが２であり、Ｒ２が、［表１］～［表３］に記載のいずれかの置換基である化合物。 Formula (L-15):
Figure JPOXMLDOC01-appb-C000039
 In the compound represented by the formula, R y is a cyano group, n is 0, and R 2 is any of the substituents described in [Table 1] to [Table 3].
In the compound represented by the formula (L-15), compounds wherein R y is a cyano group, n is 1 and R 2 is any of the substituents described in [Table 1] to [Table 3] .
In the compound represented by the formula (L-15), compounds wherein R y is a cyano group, n is 2 and R 2 is any of the substituents described in [Table 1] to [Table 3] .
In the compound represented by the formula (L-15), compounds wherein R y is a carboxy group, n is 0, and R 2 is any of the substituents described in [Table 1] to [Table 3] .
In the compound represented by the formula (L-15), compounds wherein R y is a carboxy group, n is 1 and R 2 is any of the substituents described in [Table 1] to [Table 3] .
In the compound represented by the formula (L-15), compounds wherein R y is a carboxy group, n is 2 and R 2 is any of the substituents described in [Table 1] to [Table 3] .
In the compound represented by the formula (L-15), R y is a methoxycarbonyl group, n is 0, and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound.
In the compound represented by the formula (L-15), R y is a methoxycarbonyl group, n is 1 and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound.
In the compound represented by the formula (L-15), R y is a methoxycarbonyl group, n is 2 and R 2 is any of the substituents described in [Table 1] to [Table 3] Compound.
In the compound represented by the formula (L-15), R y is an ethoxycarbonyl group, n is 0, and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound.
In the compound represented by the formula (L-15), R y is an ethoxycarbonyl group, n is 1 and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound.
In the compound represented by the formula (L-15), R y is an ethoxycarbonyl group, n is 2 and R 2 is any of the substituents described in [Table 1] to [Table 3]. Compound.
　式（Ｌ－１６）：
Figure JPOXMLDOC01-appb-C000040
 で示される化合物において、Ｒｙがシアノ基であり、ｎが０であり、Ｒ２が、フッ素原子又は塩素原子である化合物。
　式（Ｌ－１６）で示される化合物において、Ｒｙがシアノ基であり、ｎが１であり、Ｒ２が、フッ素原子又は塩素原子である化合物。
　式（Ｌ－１６）で示される化合物において、Ｒｙがシアノ基であり、ｎが２であり、Ｒ２が、フッ素原子又は塩素原子である化合物。
　式（Ｌ－１６）で示される化合物において、Ｒｙがカルボキシ基であり、ｎが０であり、Ｒ２が、フッ素原子又は塩素原子である化合物。
　式（Ｌ－１６）で示される化合物において、Ｒｙがカルボキシ基であり、ｎが１であり、Ｒ２が、フッ素原子又は塩素原子である化合物。
　式（Ｌ－１６）で示される化合物において、Ｒｙがカルボキシ基であり、ｎが２であり、Ｒ２が、フッ素原子又は塩素原子である化合物。
　式（Ｌ－１６）で示される化合物において、Ｒｙがメトキシカルボニル基であり、ｎが０であり、Ｒ２が、フッ素原子又は塩素原子である化合物。
　式（Ｌ－１６）で示される化合物において、Ｒｙがメトキシカルボニル基であり、ｎが１であり、Ｒ２が、フッ素原子又は塩素原子である化合物。
　式（Ｌ－１６）で示される化合物において、Ｒｙがメトキシカルボニル基であり、ｎが２であり、Ｒ２が、フッ素原子又は塩素原子である化合物。
　式（Ｌ－１６）で示される化合物において、Ｒｙがエトキシカルボニル基であり、ｎが０であり、Ｒ２が、フッ素原子又は塩素原子である化合物。
　式（Ｌ－１６）で示される化合物において、Ｒｙがエトキシカルボニル基であり、ｎが１であり、Ｒ２が、フッ素原子又は塩素原子である化合物。
　式（Ｌ－１６）で示される化合物において、Ｒｙがエトキシカルボニル基であり、ｎが２であり、Ｒ２が、フッ素原子又は塩素原子である化合物。 Formula (L-16):
Figure JPOXMLDOC01-appb-C000040
 In the compound shown by this, a compound in which R y is a cyano group, n is 0, and R 2 is a fluorine atom or a chlorine atom.
In the compound represented by the formula (L-16), compounds wherein R y is a cyano group, n is 1 and R 2 is a fluorine atom or a chlorine atom.
In the compound represented by the formula (L-16), compounds wherein R y is a cyano group, n is 2 and R 2 is a fluorine atom or a chlorine atom.
In the compound represented by the formula (L-16), compounds wherein R y is a carboxy group, n is 0, and R 2 is a fluorine atom or a chlorine atom.
In the compound represented by the formula (L-16), compounds wherein R y is a carboxy group, n is 1 and R 2 is a fluorine atom or a chlorine atom.
In the compound represented by the formula (L-16), compounds wherein R y is a carboxy group, n is 2 and R 2 is a fluorine atom or a chlorine atom.
In the compound represented by the formula (L-16), compounds wherein R y is a methoxycarbonyl group, n is 0, and R 2 is a fluorine atom or a chlorine atom.
In the compound represented by the formula (L-16), compounds wherein R y is a methoxycarbonyl group, n is 1 and R 2 is a fluorine atom or a chlorine atom.
In the compound represented by the formula (L-16), compounds wherein R y is a methoxycarbonyl group, n is 2 and R 2 is a fluorine atom or a chlorine atom.
In the compound represented by the formula (L-16), compounds wherein R y is an ethoxycarbonyl group, n is 0, and R 2 is a fluorine atom or a chlorine atom.
In the compound represented by the formula (L-16), compounds wherein R y is an ethoxycarbonyl group, n is 1 and R 2 is a fluorine atom or a chlorine atom.
In the compound represented by the formula (L-16), compounds wherein R y is an ethoxycarbonyl group, n is 2 and R 2 is a fluorine atom or a chlorine atom.
　本発明化合物は、下記群（ａ）、群（ｂ）、群（ｃ）、群（ｄ）、群（ｅ）、群（ｆ）、群（ｇ）及び群（ｈ）からなる群より選ばれる１以上の成分（以下、「本成分」と記す）と混用又は併用することができる。
　前記混用又は併用とは、本発明化合物と本成分とを、同時に、別々に又は時間間隔をおいて使用することを意味する。
　本発明化合物と本成分とを同時に使用する場合、本発明化合物及び本成分が、それぞれ別個の製剤に含まれていてもよく、１つの製剤に含まれていてもよい。
　本発明の１つの側面は、群（ａ）及び群（ｂ）からなる群より選ばれる１以上の成分、並びに本発明化合物を含有する組成物（以下、「組成物Ａ」と記す）である。 The compounds of the present invention are selected from the group consisting of the following groups (a), (b), (c), (d), (e), (f), (g) and (h): Can be used together or in combination with one or more components (hereinafter referred to as "the component").
The above-mentioned combined use or combined use means using the compound of the present invention and the present component simultaneously, separately or at time intervals.
When the compound of the present invention and the component are used simultaneously, the compound of the present invention and the component may be contained in separate formulations or may be contained in one formulation.
One aspect of the present invention is one or more components selected from the group consisting of group (a) and group (b), and a composition containing the compound of the present invention (hereinafter referred to as “composition A”) .
　群（ａ）は、アセチルコリンエステラーゼ阻害剤（例えばカーバメート系殺虫剤、有機リン系殺虫剤）、GABA作動性塩素イオンチャネルアンタゴニスト（例えばフェニルピラゾール系殺虫剤）、ナトリウムチャネルモジュレーター（例えば、ピレスロイド系殺虫剤）、ニコチン性アセチルコリン受容体拮抗モジュレーター（例えば、ネオニコチノイド系殺虫剤）、ニコチン性アセチルコリン受容体アロステリックモジュレーター、グルタミン酸作動性塩素イオンチャネルアロステリックモジュレーター（例えば、マクロライド系殺虫剤）、幼若ホルモンミミック、マルチサイト阻害剤、弦音器官TRPVチャネルモジュレーター、ダニ類生育阻害剤、ミトコンドリアATP生合成酵素阻害剤、酸化的リン酸化脱共役剤、ニコチン性アセチルコリン受容体チャネルブロッカー（例えば、ネライストキシン系殺虫剤）、キチン合成阻害剤、脱皮阻害剤、エクダイソン受容体アゴニスト、オクトパミン受容体アゴニスト、ミトコンドリア電子伝達系複合体I, II, III及びIVの阻害剤、電位依存性ナトリウムチャネルブロッカー、アセチルCoAカルボキシラーゼ阻害剤、リアノジン受容体モジュレーター（例えば、ジアミド系殺虫剤）、弦音器官モジュレーター、微生物殺虫剤の各々の活性成分、及びその他の殺虫・殺ダニ・殺線虫活性成分からなる群である。これらは、IRACの作用機構に基づく分類に記載されている。 Group (a) includes acetylcholinesterase inhibitors (eg carbamate insecticides, organophosphorus insecticides), GABAergic chloride ion channel antagonists (eg phenylpyrazole insecticides), sodium channel modulators (eg pyrethroid insecticides) Nicotinic acetylcholine receptor antagonistic modulators (eg, neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamatergic chloride ion channel allosteric modulators (eg, macrolide insecticides), juvenile hormone mimic , Multi-site inhibitor, chordal organ TRPV channel modulator, mite growth inhibitor, mitochondrial ATP biosynthesis enzyme inhibitor, oxidative phosphorylation uncoupling agent, nicotinic acetylcholine receptor Channel blockers (eg, nereistoxin insecticides), chitin synthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, inhibitors of mitochondrial electron transport complex I, II, III and IV, potentials -Dependent sodium channel blocker, acetyl-CoA carboxylase inhibitor, ryanodine receptor modulator (eg, diamide insecticide), chord tone organ modulator, active ingredient of each of microbial insecticides, and other insecticidal, acaricidal and nematicidal activity It is a group consisting of ingredients. These are described in the classification based on IRAC's mechanism of action.
　群（ｂ）は、核酸合成阻害剤（例えば、フェニルアミド系殺菌剤、アシルアミノ酸系殺菌剤）、細胞分裂及び細胞骨格阻害剤（例えば、MBC殺菌剤）、呼吸阻害剤（例えば、QoI殺菌剤、Qil殺菌剤）、アミノ酸合成及びタンパク質合成阻害剤（例えば、アニリノピリジン系殺菌剤）、シグナル伝達阻害剤、脂質合成及び膜合成阻害剤、ステロール生合成阻害剤（例えば、トリアゾール系などのDMI殺菌剤）、細胞壁合成阻害剤、メラニン合成阻害剤、植物防御誘導剤、多作用点接触活性殺菌剤、微生物殺菌剤の各々の活性成分、及びその他の殺菌活性成分からなる群である。これらは、FRACの作用機構に基づく分類に記載されている。 Group (b) includes nucleic acid synthesis inhibitors (eg, phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeleton inhibitors (eg, MBC fungicides), respiratory inhibitors (eg, QoI fungicides) , Qil fungicides), amino acid synthesis and protein synthesis inhibitors (eg, anilinopyridine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (eg, triazole etc. DMI) And bactericidal agents, cell wall synthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-active point contact active disinfectants, active ingredients of microbial disinfectants, and other bactericidal active ingredients. These are described in the classification based on the mechanism of action of FRAC.
　群（ｃ）は、植物成長調整成分（菌根菌及び根粒菌を含む）の群である。 Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).
　群（ｄ）は、薬害軽減成分の群である。 Group (d) is a group of safeners.
　群（ｅ）は、共力剤の群である。 Group (e) is a group of synergists.
　群（ｆ）は、鳥忌避成分、昆虫忌避成分、動物忌避成分からなる忌避成分の群である。 Group (f) is a group of repellent components consisting of a bird repellent component, an insect repellent component and an animal repellent component.
　群（ｇ）は、殺軟体動物成分の群である。 Group (g) is a group of mollusc components.
　群（ｈ）は、昆虫フェロモンの群である。 Group (h) is a group of insect pheromone.
　以下に、本成分と本発明化合物の組み合わせの例を記載する。例えば、アラニカルブ（alanycarb）+SXはアラニカルブ（alanycarb）とSXとの組合せを意味する。
　なお、SXの略号は、化合物群SX1～SX74から選ばれるいずれか１つの本発明化合物を意味する。また、以下に記載する本成分はいずれも公知の成分であり、市販の製剤から得るか、公知の方法により製造することができる。本成分が微生物の場合は、菌寄託機関から入手することもできる。なお、括弧内の数字はCAS RN（登録商標）を表す。 Below, the example of the combination of this component and this invention compound is described. For example, alanicarb (Salyx + SX) means a combination of alanicarb (Salyx).
The abbreviation SX means any one compound of the present invention selected from the compound groups SX1 to SX74. In addition, all of the components described below are known components and can be obtained from commercially available preparations or can be produced by known methods. When the component is a microorganism, it can also be obtained from a bacteria depository. The numbers in parentheses indicate CAS RN (registered trademark).
上記群（ａ）の本成分と本発明化合物との組み合わせ：
　アバメクチン（abamectin）+SX、アセフェート（acephate）+SX、アセキノシル（acequinocyl）+SX、アセタミプリド（acetamiprid）+SX、アクリナトリン（acrinathrin）+SX、アシノナピル（acynonapyr）+SX、アフィドピロペン（afidopyropen）+SX、アフォキソラネル（afoxolaner）+SX、アラニカルブ（alanycarb）+SX、アルジカルブ（aldicarb）+SX、アレスリン（allethrin）+SX、アルファシペルメトリン（alpha-cypermethrin）+SX、アルファエンドスルファン（alpha-endosulfan）+SX、リン化アルミニウム（aluminium phosphide）+SX、アミトラズ（amitraz）+SX、アザジラクチン（azadirachtin）+SX、アザメチホス（azamethiphos）+SX、アジンホスエチル（azinphos-ethyl）+SX、アジンホスメチル（azinphos-methyl）+SX、アゾシクロチン（azocyclotin）+SX、Celastrus angulatus樹皮（bark of Celastrus angulatus)+SX、ベンダイオカルブ（bendiocarb）+SX、ベンフルトリン（benfluthrin）+SX、ベンフラカルブ（benfuracarb）+SX、ベンスルタップ（bensultap）+SX、ベンゾキシメート（benzoximate）+SX、ベンズピリモキサン（benzpyrimoxan）+SX、ベータシフルトリン（beta-cyfluthrin）+SX、べータシペルメトリン（beta-cypermethrin）+SX、ビフェナゼート（bifenazate）+SX、ビフェントリン（bifenthrin）+SX、ビオアレスリン（bioallethrin）+SX、ビオレスメトリン（bioresmethrin）+SX、ビストリフルロン（bistrifluron）+SX、ホウ砂（borax）+SX、ホウ酸（boric acid）+SX、ブロフラニリド（broflanilide）+SX、ブロモプロピレート（bromopropylate）+SX、ブプロフェジン（buprofezin）+SX、ブトカルボキシム（butocarboxim）+SX、ブトキシカルボキシム（butoxycarboxim）+SX、カズサホス（cadusafos）+SX、シアン化カルシウム（calcium cyanide）+SX、リン化カルシウム（calcium phosphide）+SX、カルバリル（carbaryl）+SX、カルボフラン（carbofuran）+SX、カルボスルファン（carbosulfan）+SX、カルタップ塩酸塩（cartap hydrochloride）+SX、カルタップ（cartap）+SX、キノメチオナート（chinomethionat）+SX、クロラントラニリプロール（chlorantraniliprole）+SX、クロルデン（chlordane）+SX、クロレトキシホス（chlorethoxyfos）+SX、クロルフェナピル（chlorfenapyr）+SX、クロルフェンビンホス（chlorfenvinphos）+SX、クロルフルアズロン（chlorfluazuron）+SX、クロルメホス（chlormephos）+SX、クロルピクリン（chloropicrin）+SX、クロルピリホス（chlorpyrifos）+SX、クロルピリホスメチル（chlorpyrifos-methyl）+SX、クロマフェノジド（chromafenozide）+SX、クロフェンテジン（clofentezine）+SX、クロチアニジン（clothianidin）+SX、クマホス（coumaphos）+SX、クリオライト（cryolite）+SX、シアノホス（cyanophos）+SX、シアントラニリプロール（cyantraniliprole）+SX、シクラニリプロール（cycloniliprole）+SX、シクロプロトリン（cycloprothrin）+SX、シクロキサプリド（cycloxaprid）+SX、シエノピラフェン（cyenopyrafen）+SX、シフルメトフェン（cyflumetofen）+SX、シフルトリン（cyfluthrin）+SX、シハロジアミド（cyhalodiamide）+SX、シハロトリン（cyhalothrin）+SX、シヘキサチン（cyhexatin）+SX、シペルメトリン（cypermethrin）+SX、シフェノトリン（cyphenothrin）+SX、シロマジン（cyromazine）+SX、ダゾメット（dazomet）+SX、デルタメトリン（deltamethrin）+SX、デメトン－S－メチル（demeton-S-methyl）+SX、ジアフェンチウロン（diafenthiuron）+SX、ダイアジノン（diazinon）+SX、ジクロルボス（dichlorvos）+SX、ジクロロメゾチアズ（dicloromezotiaz）+SX、ジコホル（dicofol）+SX、ジクロトホス（dicrotophos）+SX、ジフロビダジン（diflovidazin）+SX、ジフルベンズロン（diflubenzuron）+SX、ジメフルトリン（dimefluthrin）+SX、ジメトエート（dimethoate）+SX、ジメチルビンホス（dimethylvinphos）+SX、ジノテフラン（dinotefuran）+SX、八ホウ酸二ナトリウム（disodium octaborate）+SX、ジスルホトン（disulfoton）+SX、DNOC（2-methyl-4,6-dinitrophenol）+SX、ドラメクチン（doramectin）+SX、セイヨウオシダ乾燥葉（dried leaves of Dryopteris filix-mas)+SX、エマメクチン安息香酸塩（emamectin-benzoate）+SX、エンペントリン（empenthrin）+SX、エンドスルファン（endosulfan）+SX、EPN（O-ethyl O-(4-nitrophenyl) phenylphosphonothioate）+SX、イプシロンメトフルトリン（epsilon-metofluthrin）+SX、イプシロンモンフルオロトリン（epsilon-momfluorothrin）+SX、エスフェンバレレート（esfenvalerate）+SX、エチオフェンカルブ（ethiofencarb）+SX、エチオン（ethion）+SX、エチプロール（ethiprole）+SX、エトプロホス（ethoprophos）+SX、エトフェンプロックス（etofenprox）+SX、エトキサゾール（etoxazole）+SX、ニガヨモギ抽出物（extract of Artemisia absinthium)+SX、Cassia nigricans抽出物（extract of Cassia nigricans)+SX、クリトリア・テルナテアの抽出物（extract of clitoria ternatea）+SX、ヒレハリソウ抽出物（extract of Symphytum officinale)+SX、アリタソウ抽出物（extracts or simulated blend of Chenopodium ambrosioides)+SX、タンジー抽出物（extract of Tanacetum vulgare)+SX、セイヨウイラクサ抽出物（extract of Urtica dioica)+SX、ヤドリギ抽出物（extract of Viscum album)+SX、ファンフル（famphur）+SX、フェナミホス（fenamiphos）+SX、フェナザキン（fenazaquin）+SX、酸化フェンブタスズ（fenbutatin oxide）+SX、フェニトロチオン（fenitrothion）+SX、フェノブカルブ（fenobucarb）+SX、フェノキシカルブ（fenoxycarb）+SX、フェンプロパトリン（fenpropathrin）+SX、フェンピロキシメート（fenpyroximate）+SX、フェンチオン（fenthion）+SX、フェンバレレート（fenvalerate）+SX、フィプロニル（fipronil）+SX、フロメトキン（flometoquin）+SX、フロニカミド（flonicamid）+SX、フルアクリピリム（fluacrypyrim）+SX、フルアザインドリジン（fluazaindolizine）+SX、フルアズロン（fluazuron）+SX、フルベンジアミド（flubendiamide）+SX、フルシクロクスロン（flucycloxuron）+SX、フルシトリネート（flucythrinate）+SX、フルエンスルホン（fluensulfone）+SX、フルフェンプロックス（flufenoprox）+SX、フルフェノクスロン（flufenoxuron）+SX、フルフィプロール（flufiprole）+SX、フルメトリン（flumethrin）+SX、フルオピラム（fluopyram）+SX、フルピラジフロン（flupyradifurone）+SX、フルピリミン（flupyrimin）+SX、フルララネル（fluralaner）+SX、フルバリネート（fluvalinate）+SX、フルキサメタミド（fluxametamide）+SX、ホルメタネート（formetanate）+SX、ホスチアゼート（fosthiazate）+SX、フラメトリン（furamethrin）+SX、フラチオカルブ（furathiocarb）+SX、ガンマシハロトリン（gamma-cyhalothrin）+SX、GS-オメガ/カッパHXTX-Hv1aペプチド（GS-omega/kappa HXTX-Hv1a peptide）+SX、ハルフェンプロックス（halfenprox）+SX、ハロフェノジド（halofenozide）+SX、ヘプタフルトリン（heptafluthrin）+SX、ヘプテノホス（heptenophos）+SX、ヘキサフルムロン（hexaflumuron）+SX、ヘキシチアゾクス（hexythiazox）+SX、ホップベータ酸のカリウム塩（potassium salt of hop beta acid）+SX、ヒドラメチルノン（hydramethylnon）+SX、ヒドロプレン（hydroprene）+SX、イミシアホス（imicyafos）+SX、イミダクロプリド（imidacloprid）+SX、イミプロトリン（imiprothrin）+SX、インドキサカルブ（indoxacarb）+SX、イソフェンホス（isofenphos）+SX、イソプロカルブ（isoprocarb）+SX、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（isopropyl-O-(methoxyaminothiophosphoryl)salicylate）+SX、イソキサチオン（isoxathion）+SX、イベルメクチン（ivermectin）+SX、カデスリン（kadethrin）+SX、カッパテフルトリン（kappa-tefluthrin）+SX、カッパビフェントリン（kappa-bifenthrin）+SX、キノプレン（kinoprene）+SX、ラムダシハロトリン（lambda-cyhalothrin）+SX、レピメクチン（lepimectin）+SX、石灰硫黄合剤（lime sulfur）+SX、ルフェヌロン（lufenuron）+SX、マシン油（machine oil）+SX、マラチオン（malathion）+SX、メカルバム（mecarbam）+SX、メペルフルトリン（meperfluthrin）+SX、メタフルミゾン（metaflumizone）+SX、メタム（metam）+SX、メタミドホス（methamidophos）+SX、メチダチオン（methidathion）+SX、メチオカルブ（methiocarb）+SX、メソミル（methomyl）+SX、メトプレン（methoprene）+SX、メトキシクロル（methoxychlor）+SX、メトキシフェノジド（methoxyfenozide）+SX、臭化メチル（methyl bromide）+SX、メトフルトリン（metofluthrin）+SX、メトルカルブ（metolcarb）+SX、メトキサジアゾン（metoxadiazone）+SX、メビンホス（mevinphos）+SX、ミルベメクチン（milbemectin）+SX、ミルベマイシンオキシム（milbemycin oxime）+SX、モンフルオロトリン（momfluorothrin）+SX、モノクロトホス（monocrotophos）+SX、モキシデクチン（moxidectin）+SX、ナレッド（naled）+SX、ニコチン（nicotine）+SX、硫酸ニコチン（nicotine-sulfate）+SX、ニテンピラム（nitenpyram）+SX、ノバルロン（novaluron）+SX、ノビフルムロン（noviflumuron）+SX、アメリカアリタソウ種子油（oil of the seeds of Chenopodium anthelminticum)+SX、オメトエート（omethoate）+SX、オキサミル（oxamyl）+SX、オキシジメトンメチル（oxydemeton-methyl）+SX、パラチオン（parathion）+SX、パラチオンメチル（parathion-methyl）+SX、ペルメトリン（permethrin）+SX、フェノトリン（phenothrin）+SX、フェントエート（phenthoate）+SX、ホレート（phorate）+SX、ホサロン（phosalone）+SX、ホスメット（phosmet）+SX、ホスファミドン（phosphamidon）+SX、ホスフィン（phosphine）+SX、ホキシム（phoxim）+SX、ピリミカーブ（pirimicarb）+SX、ピリミホスメチル（pirimiphos-methyl）+SX、シアン化カリウム（potassium cyanide）+SX、プラレトリン（prallethrin）+SX、プロフェノホス（profenofos）+SX、プロフルトリン（profluthrin）+SX、プロパルギット（propargite）+SX、プロペタムホス（propetamphos）+SX、プロポキスル（propoxur）+SX、アルギニン酸プロピレングリコール（propylene glycol alginate）+SX、プロチオホス（prothiofos）+SX、ピフルブミド（pyflubumide）+SX、ピメトロジン（pymetrozine）+SX、ピラクロホス（pyraclofos）+SX、ピレトリン（pyrethrins）+SX、ピリダベン（pyridaben）+SX、ピリダリル（pyridalyl）+SX、ピリダフェンチオン（pyridaphenthion）+SX、ピリフルキナゾン（pyrifluquinazone）+SX、ピリミジフェン（pyrimidifen）+SX、ピリミノストロビン（pyriminostrobin）+SX、ピリプロール（pyriprole）+SX、ピリプロキシフェン（pyriproxyfen）+SX、キナルホス（quinalphos）+SX、レスメトリン（resmethrin）+SX、ロテノン（rotenone）+SX、リアノジン（ryanodine)+SX、セラメクチン（selamectin）+SX、シグマシペルメトリン（sigma-cypermethrin）+SX、シラフルオフェン（silafluofen）+SX、ホウ酸ナトリウム（sodium borate）+SX、シアン化ナトリウム（sodium cyanide）+SX、メタホウ酸ナトリウム（sodium metaborate）+SX、スピネトラム（spinetoram）+SX、スピノサド（spinosad）+SX、スピロジクロフェン（spirodiclofen）+SX、スピロメシフェン（spiromesifen）+SX、スピロピジオン(spiropidion)+SX、スピロテトラマト（spirotetramat）+SX、スルフルラミド（sulfluramid）+SX、スルホテップ（sulfotep）+SX、スルホキサフロル（sulfoxaflor）+SX、硫黄（sulfur）+SX、フッ化スルフリル（sulfuryl fluoride）+SX、吐酒石（tartar emetic）+SX、タウフルバリネート（tau-fluvalinate）+SX、テブフェノジド（tebufenozide）+SX、テブフェンピラド（tebufenpyrad）+SX、テブピリムホス（tebupirimfos）+SX、テフルベンズロン（teflubenzuron）+SX、テフルトリン（tefluthrin）+SX、テメホス（temephos）+SX、テルブホス（terbufos）+SX、アリタソウから抽出したテルペン成分（terpene constitue
nts of the extract of chenopodium ambrosioides near ambrosioides、Brand name：Terpenoid blend QRD 460）+SX、テトラクロルビンホス（tetrachlorvinphos）+SX、テトラジホン（tetradifon）+SX、テトラメトリン（tetramethrin）+SX、テトラメチルフルトリン（tetramethylfluthrin）+SX、テトラニリプロール（tetraniliprole）+SX、シータシペルメトリン（theta-cypermethrin）+SX、チアクロプリド（thiacloprid）+SX、チアメトキサム（thiamethoxam）+SX、チオシクラム（thiocyclam）+SX、チオジカルブ（thiodicarb）+SX、チオファノックス（thiofanox）+SX、チオメトン（thiometon）+SX、チオスルタップ二ナトリウム塩（thiosultap-disodium）+SX、チオスルタップ一ナトリウム塩（thiosultap-monosodium）+SX、チオキサザフェン（tioxazafen）+SX、トルフェンピラド（tolfenpyrad）+SX、トラロメトリン（tralomethrin）+SX、トランスフルトリン（transfluthrin）+SX、トリアザメート（triazamate）+SX、トリアゾホス（triazophos）+SX、トリクロルホン（trichlorfon）+SX、トリフルメゾピリム（triflumezopyrim）+SX、トリフルムロン（triflumuron）+SX、トリメタカルブ（trimethacarb）+SX、チクロピラゾフロル（tyclopyrazoflor）+SX、バミドチオン（vamidothion）+SX、スリナムニガキ木材抽出成分（wood extract of Quassia amara）+SX、XMC（3,5-dimethylphenyl N-methylcarbamate）+SX、キシリルカルブ（xylylcarb）+SX、ゼータシペルメトリン（zeta-cypermethrin）+SX、リン化亜鉛（zinc phosphide）+SX、３－ブロモ－Ｎ－［２，４－ジクロロ－６－（メチルカルバモイル）フェニル］－１－（３，５－ジクロロピリジン－２－イル）－１Ｈ－ピラゾール－５－カルボキサミド（1104384-14-6）+SX、Ｎ－［３－クロロ－１－（ピリジン－３－イル）－１Ｈ－ピラゾール－４－イル］－Ｎ－エチル－３－（３，３，３－トリフルオロプロパンスルフィニル）プロパンアミド（1477923-37-7）+SX、２－［３－（エタンスルホニル）ピリジン－２－イル］－５－（トリフルオロメタンスルホニル）ベンゾオキサゾール（1616678-32-0）+SX、４－［５－（３，５－ジクロロフェニル）－５－（トリフルオロメチル）－４，５－ジヒドロ－１，２－オキサゾール－３－イル］－２－メチル－Ｎ－（１－オキソチエタン－３－イル）ベンズアミド（1241050-20-3）+SX、３－メトキシ－Ｎ－（５－｛５－（トリフルオロメチル）－５－［３－（トリフルオロメチル）フェニル］－４，５－ジヒドロ－１，２－オキサゾール－３－イル｝インダン－１－イル）プロパンアミド（1118626-57-5）+SX、Ｎ－［２－ブロモ－６－クロロ－４－（１，１，１，２，３，３，３－ヘプタフルオロプロパン－２－イル）フェニル］－３－｛エチル［（ピリジン－４－イル）カルボニル］アミノ｝－２－メトキシベンズアミド（1429513-53-0）+SX、Ｎ－［２－ブロモ－６－クロロ－４－（１，１，１，２，３，３，３－ヘプタフルオロプロパン－２－イル）フェニル］－３－［エチル（４－シアノベンゾイル）アミノ］－２－メトキシベンズアミド（1609007-65-9）+SX、Ｎ－［２－ブロモ－６－ジフルオロメトキシ－４－（１，１，１，２，３，３，３－ヘプタフルオロプロパン－２－イル）フェニル］－３－｛メチル［（ピリジン－４－イル）カルボニル］アミノ｝－２－メトキシベンズアミド（1630969-78-6）+SX、１－｛２－フルオロ－４－メチル－５－［（２，２，２－トリフルオロエチル）スルフィニル］フェニル｝－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－５－アミン（885026-50-6）+SX、BT作物のタンパク質Cry1Ab（BT crop protein Cry1Ab）+SX、BT作物のタンパク質Cry1Ac（BT crop protein Cry1Ac）+SX、BT作物のタンパク質Cry1Fa（BT crop protein Cry1Fa）+SX、BT作物のタンパク質Cry1A.105（BT crop protein Cry1A.105）+SX、BT作物のタンパク質Cry2Ab（BT crop protein Cry2Ab）+SX、BT作物のタンパク質Vip3A（BT crop protein Vip3A）+SX、BT作物のタンパク質ｍCry3A（BT crop protein Cry3A）+SX、BT作物のタンパク質Cry3Ab（BT crop protein Cry3Ab）+SX、BT作物のタンパク質Cry3Bb（BT crop protein Cry3Bb）+SX、BT作物のタンパク質Cry34Ab1/Cry35Ab1（BT crop protein Cry34Ab1/Cry35Ab1）+SX、アドクソフィエス・オラナ顆粒病ウイルス(Adoxophyes orana granulosis virus) +SX、アンチカルシア・ゲマタリス核多角体病ウイルス(Anticarsia gemmatalis mNPV) +SX、オートグラファ・カリフォルニア核多角体病ウイルスFV#11 (Autographa californica mNPV FV#11) +SX、シジア・ポモネラ顆粒病ウイルス V15(Cydia pomonella GV V15) +SX、シジア・ポモネラ顆粒病ウイルスV22 (Cydia pomonella GV V22) +SX、クリプトフレビア・ロイコトレタ顆粒病ウイルス(Cryptophlebia leucotreta GV) +SX、デンドロリムス・プンクタタス細胞質多面体ウイルス (Dendrolimus punctatus cypovirus) +SX 、ヘリコベルパ・アルミゲラ核多角体病ウイルスBV-0003株(Helicoverpa armigera NPV BV-0003) +SX、ヘリコベルパ・ゼア核多角体病ウイルス(Helicoverpa zea NPV) +SX、リュマントリア・ディスパル核多角体病ウイルス(Lymantria dispar NPV) +SX、マメストラ・ブラシカエ核多角体病ウイルス（Mamestra brassicae NPV）+SX、マメストラ・コンフィグラタ核多角体病ウイルス（Mamestra configurata NPV）+SX、ネオディプリオン・アビエンティス核多角体病ウイルス(Neodiprion abietis NPV) +SX、ネオディプリオン・レコンテイ核多角体病ウイルス(Neodiprion lecontei NPV) +SX、ネオディプリオン・セルティファー核多角体病ウイルス(Neodiprion sertifer NPV) +SX、ノゼマ・ロクスタエ(Nosema locustae) +SX、オルギイア・プソイドツガタ核多角体病ウイルス（Orgyia pseudotsugata NPV）+SX、ピエリス・ラパエ顆粒病ウイルス(Pieris rapae GV) +SX、プロジア・インテルプンクテラ顆粒病ウイルス（Plodia interpunctella GV）+SX、スポドプテラ・エクシグア核多角体病ウイルス(Spodoptera exigua mNPV) +SX、スポドプテラ・リットラリス核多角体病ウイルス(Spodoptera littoralis mNPV) +SX、スポドプテラ・リツラ核多角体病ウイルス(Spodoptera litura NPV) +SX、アルスロボトリス・ダクチロイデス（Arthrobotrys dactyloides）+SX、バチルス・フィルムスGB-126株（Bacillus firmus GB-126）+SX、バチルス・フィルムスI-1582株（Bacillus firmus I-1582）+SX、バチルス・メガテリウム（Bacillus megaterium）+SX、バチルス sp. AQ175株（Bacillus sp.AQ175）+SX、バチルス sp.AQ177株（Bacillus sp.AQ177）+SX、バチルス sp.AQ178株（Bacillus sp.AQ178）+SX、バチルス・スファエリクス2362（Bacillus sphaericus 2362）+SX、バチルス・スファエリクスABTS1743株（Bacillus sphaericus ABTS1743）+SX、バチルス・スファエリクスSerotype H5a5b株（Bacillus sphaericus Serotype H5a5b）+SX、バチルス・チューリンゲンシスAQ52株（Bacillus thuringiensis AQ52）+SX、バチルス・チューリンゲンシスBD#32株（Bacillus thuringiensis BD#32）+SX、バチルス・チューリンゲンシスCR-371株（Bacillus thuringiensis CR-371）+SX、バチルス・チューリンゲンシス・アイザワイ亜種ABTS-1857株（Bacillus thuringiensis subsp. Aizawai ABTS-1857）+SX、バチルス・チューリンゲンシス・アイザワイ亜種AM65-52株（Bacillus thuringiensis subsp. Aizawai AM65-52）+SX、バチルス・チューリンゲンシス・アイザワイ亜種GC-91株（Bacillus thuringiensis subsp. Aizawai GC-91）+SX、バチルス・チューリンゲンシス・アイザワイ亜種Serotype H-7株（Bacillus thuringiensis subsp. Aizawai Serotype H-7）+SX、バチルス・チューリンゲンシス・クリスターキ亜種ABTS351株（Bacillus thuringiensis subsp. Kurstaki ABTS351）+SX、バチルス・チューリンゲンシス・クリスターキ亜種BMP123株（Bacillus thuringiensis subsp. Kurstaki BMP123）+SX、バチルス・チューリンゲンシス・クリスターキ亜種EG234株（Bacillus thuringiensis subsp. Kurstaki EG234）+SX、バチルス・チューリンゲンシス・クリスターキ亜種EG7841株（Bacillus thuringiensis subsp. Kurstaki EG7841）+SX、バチルス・チューリンゲンシス・クリスターキ亜種EVB113-19株（Bacillus thuringiensis subsp. Kurstaki EVB113-19）+SX、バチルス・チューリンゲンシス・クリスターキ亜種F810株（Bacillus thuringiensis subsp. Kurstaki F810）+SX、バチルス・チューリンゲンシス・クリスターキ亜種HD-1株（Bacillus thuringiensis subsp. Kurstaki HD-1）+SX、バチルス・チューリンゲンシス・クリスターキ亜種PB54株（Bacillus thuringiensis subsp. Kurstaki PB54）+SX、バチルス・チューリンゲンシス・クリスターキ亜種SA-11株（Bacillus thuringiensis subsp. Kurstaki SA-11）+SX、バチルス・チューリンゲンシス・クリスターキ亜種SA-12株（Bacillus thuringiensis subsp. Kurstaki SA-12）+SX、バチルス・チューリンゲンシス・テネブリオシス亜種NB176株（Bacillus thuringiensis subsp. Tenebriosis NB176）+SX、バチルス・チューリンゲンシス・チューリンゲンシス亜種MPPL002株（Bacillus thuringiensis subsp. Thuringiensis MPPL002）+SX、バチルス・チューリンゲンシス・モリソニ亜種株（Bacillus thuringiensis subsp.morrisoni）+SX、バチルス・チューリンゲンシス・コルメリ変種（Bacillus thuringiensis var. colmeri）+SX、バチルス・チューリンゲンシス・ダームスタディエンシス変種24-91株（Bacillus thuringiensis var. darmstadiensis 24-91）+SX、バチルス・チューリンゲンシス・デンドロリムス変種株（Bacillus thuringiensis var. dendrolimus）+SX、バチルス・チューリンゲンシス・ガレリア変種株（Bacillus thuringiensis var. galleriae）+SX、バチルス・チューリンゲンシス・イスラエレンシス変種BMP144株（Bacillus thuringiensis var. israelensis BMP144）+SX、バチルス・チューリンゲンシス・イスラエレンシス変種serotypeH-14株（Bacillus thuringiensis var. israelensis serotypeH-14）+SX、バチルス・チューリンゲンシス・ジャポネンシス変種buibui株（Bacillus thuringiensis var. japonensis buibui）+SX、バチルス・チューリンゲンシス・サンディエゴ変種M-7株（Bacillus thuringiensis var. san diego M-7）+SX、バチルス・チューリンゲンシス・7216変種株（Bacillus thuringiensis var.7216）+SX、バチルス・チューリンゲンシス・アエジプチ変種株（Bacillus thuringiensis var.aegypti）+SX、バチルス・チューリンゲンシス・T36変種株（Bacillus thuringiensis var.T36）+SX、ボーベリア・バシアーナANT-03株（Beauveria bassiana ANT-03）+SX、ボーベリア・バシアーナATCC74040株（Beauveria bassiana ATCC74040）+SX、ボーベリア・バシアーナGHA株（Beauveria bassiana GHA）+SX、ボーベリア・ブロンニアティ（Beauveria brongniartii）+SX、バークホルデリア・リノジェンシスA396株（Burkholderia rinojensis A396）+SX、クロモバクテリウム・サブツガエPRAA4-1T株（Chromobacterium subtsugae PRAA4-1T）+SX、ダクチレラ・エリプソスポラ（Dactyllela ellipsospora）+SX、デクチラリア・サウマシア（Dectylaria thaumasia）＋SX、ヒルステラ・ミネソテンシス（Hirsutella minnesotensis）+SX、ヒルステラ・ロッシリエンシス（Hirsutella rhossiliensis）+SX、ヒルステラ・トンプソニ（Hirsutella thompsonii）+SX、ラゲニジウム・ギガンテウム（Lagenidium giganteum）+SX、レカニシリウム・レカニ KV01株（Lecanicillium lecanii KV01）+SX、レカニシリウム・レカニDAOM198499株の分生子（Lecanicillium lecanii conidia of strain DAOM198499）+SX、レカニシリウム・レカニDAOM216596株の分生子（Lecanicillium lecanii conidia of strain DAOM216596）+SX、メタリジウム・アニソプリアエF52株（Metarhizium anisopliae F52）+SX、メタリジウム・アニソプリアエ・アクリダム変種株（Metarhizium anisopliae var. acridum)+SX、メタリジウム・フラボビリデ（Metarhizium flavoviride）+SX、モナクロスポリウム・フィマトパガム（Monacrosporium phymatopagum）+SX、
ペキロマイセス・フモソロセウスApopka97株（Paecilomyces fumosoroseus Apopka97）+SX、ペキロマイセス・リラシナス251株（Paecilomyces lilacinus 251）+SX、ペキロマイセス・テヌイペスT1株（Paecilomyces tenuipes T1）+SX、パエニバチルス・ポピリア（Paenibacillus popilliae）+SX、パスツーリア・ニシザワエPn1株（Pasteuria nishizawae Pn1）+SX、パスツーリア・ペネトランス（Pasteuria penetrans）+SX、パスツーリア・ウスガエ（Pasteuria usgae）+SX、パスツーリア・トイネイ（Pasteuria thoynei）+SX、セラチア・エントモフィラ（Serratia entomophila）+SX、バーティシリウム・クラミドスポリウム（Verticillium chlamydosporium）+SX、バーティシリウム・レカニNCIM1312株（Verticillium lecani NCIM1312）+SX。 A combination of the present component of the above group (a) with the compound of the present invention:
Abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acririnathrin + SX, acynonapyr + SX, afidopyropene + SX, afoxolaneal (Afoxolaner) + SX, alaniccarb (alanycarb) + SX, aldicarb (aldicarb) + SX, allethrin + SX, alpha-cypermethrin (alpha-cypermethrin) + SX, alpha-endosulfan (alpha-endosulfan) + SX, phosphorylated Aluminum (phosphide) + SX, amitraz (Amitraz) + SX, azadirachtin + SX, azamethiphos (Azamethiphos) + SX, azinphos-ethyl (azinphos-ethyl) + SX, azinphos-methyl (azinphos-methyl) + SX, azocyclotin (azocyclotintin) ) + SX, Celastrus angulatus bark (bark of Celastrus angulatus) + SX, benda cio b arb) + SX, benfluthrin + SX, benfuracarb + SX, bensultap + SX, benzoximate + SX, benzpyrimoxan + SX, beta-cifluthrin (beta) -cyfluthrin) + SX, betacypermethrin (beta-cypermethrin) + SX, bifenazate + SX, bifenthrin + SX, bioallethrin + SX, bioresmethrin (bioresmethrin) + SX, bistrifluron (Bistrifluron) + SX, borax (borax) + SX, boric acid (boric acid) + SX, brofuranilide + SX, bromopropylate + SX, buprofezin + SX, butocarbox ( butocarboxim) + SX, butoxycarboxim + SX, cadusafos + SX, calcium cyanide + SX, calcium phosphide calcium phosphide) + SX, carbaryl (carbaryl) + SX, carbofuran (carbofuran) + SX, carbosulfan (carbosulfan) + SX, cartap hydrochloride (Cartap hydrochloride) + SX, cartap (cartap) + SX, quinomethionate (chinomethionat) + SX, chlorantraniliprole + SX, chlordane + SX, chlorethoxyfos + SX, chlorfenapyr + SX, chlorfenvinphos (chlorfenvinphos) + SX, chlorfluazuron ( chlorfluazuron) + SX, chlormephos + SX, chlorpicrin (chloropicrin) + SX, chlorpyrifos (chloropyrifos) + SX, chlorpyrifos methyl (chlorpyrifos-methyl) + SX, chromofenozide + SX, clofentezine SX, clothianidin + SX, coumaphos + co, SX, cryolite + SX, cyanophos (Cyanophos) + SX, cyantraniliprole (Cyantraniliprole) + SX, cyclaniliprole (cycliciliprole) + SX, cycloprothrin (cycloprothrin) + SX, cycloxaprid (cyclopaprid) + SX, cenopyraphen (cyenopyrafen) + SX, cyflumethofen + SX, cyfluthrin + SX, cyhalodiamide + SX, cyhalothrin + SX, cyhexatin + SX, cypermethrin (cypermethrin) + SX, cyphenothrin (cyphenothrin) + SX, cyromazine + SX, dazomet (dazomet) + SX, deltamethrin (deltamethrin) + SX, demeton-S-methyl (demeton-S-methyl) + SX, diafenthiuron (diafenthiuron) + SX, diazinon (Diazinon) + SX, dichlorvos (dichlorvos) + SX, dichloro mezothiaz (dicloromezotiaz) + SX, dicofol (dicofol) + SX, diclos Phos (dicrotophos) + SX, diflovidazin + SX, diflubenzuron + SX, dimefluthrin + SX, dimethoate + SX, dimethylvinphos (dimethylvinphos) + SX, dinotefuran (dinotefuran) + SX , Disodium octaborate + SX, disulfoton + SX, DNOC (2-methyl-4, 6-dinitrophenol) + SX, doramectin + SX, dried leaves of dried leaves (dried leaves of Dryopteris filix-mas) + SX, emamectin-benzoate + SX, empenthrin + SX, endosulfan (endosulfan) + SX, EPN (O-ethyl O- (4-nitrophenyl) phenylphosphothioate) + SX Epsilon-methoflthrin (epsilon-metofluthrin) + SX, epsilon-mon-fluorothrin (epsilon-momfluorothrin) + SX, esfenvalerate (esfenvalerate) + SX, ethiophene cal (Ethiofencarb) + SX, ethion + SX, ethiprole + SX, ethoprophos (Ethoprophos) + SX, etofenprox + SX, etoxazole + SX, extract of Artemisia (extract of Artemisia) abstinthium) + SX, Cassia nigricans extract (extract of Cassia nigricans) + SX, extract of Clitoria ternatea (extract of clitoria ternatea) + SX, extract of Symphytum officinale + SX, extract of Agarum (extractus) or simulated blend of Chenopodium ambrosioides + SX, extract of Tanacetum vulgare + SX, Stinging nettle extract (extract of Urtica dioica) + SX, mistletoe extract (extract of Viscum album) + SX, funful famphur) + SX, fenamiphos (SEN) + SX, fenazaquin + SX, fenbutatin oxide + SX, fennitrothion + SX, Nobucarb (fenobucarb) + SX, fenoxycarb (SX), fenpropathrin (SX), fenpyroximate + SX, fenthion + SX, fenvalerate (SVA) + SX, fipronil (fipronil) + SX, flometoquin + SX, flonicamide + SX, fluacrypyrim + SX, fluazaindolizine + SX, fluazuron + SX, flubendiamide + SX, full Cycloxuron + SX, flucythrinate + SX, fluensulfone + SX, flufenoprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, fluopyram + SX, flupyradiflon (flupy radifurone + SX, flupyrimin + SX, fluralaner + SX, fluvalinate (+ fluxinate) + SX, fluxamethamide + SX, formetanate (formetanate) + SX, fosthiazate + SX, flamethrin furamethrin) + SX, furathiocarb + SX, gamma cyhalothrin (gamma-cyhalothrin) + SX, GS-omega / kappa HXTX-Hv1a peptide (GS-omega / kappa HXTX-Hv 1a peptide) + SX, halfenprox (Halfenprox) + SX, halofenozide + SX, heptafluthrin + SX, heptenophos (heptenophos) + SX, hexaflumuron + SX, hexythiazox + SX, potassium of hop beta acids Salt (potassium salt of hop beta acid) + SX, hydramethylnon (hydramethylnon) + SX, hydroprene (hydroprene) + SX, imiciaphos (imicyafos) + SX Imidacloprid + SX, Imiprothrin + SX, Indoxacarb + SX, isofenphos + SX, Isoprocarb + SX, Isopropyl O- (methoxyaminothiophosphoryl) salicylate (isopropyl-) O- (methoxyaminothiophosphoryl) salicylate) + SX, isoxathion + SX, ivermectin + SX, kadethrin + SX, kappa-tefluthrin + SX, kappa bifenthrin + SX, Kinoprene + SX, Lambda Cyhalothrin + SX, Lepimectin + SX, Lime Sulfur Combination (lime sulfur) + SX, Lufenuron + SX, Machine oil (machine oil) + SX, malathion + SX, mecarbam (mecarbam) + SX, meperfluthrin + SX, metaflumizo (Metaflumizone) + SX, metam (metam) + SX, methamidophos (methhamidophos) + SX, methidathion + SX, methiocarb (methiocarb) + SX, methomil + SX, methoprene (methoprene) + SX, methoxychlor methoxychlor) + SX, methoxyfenozide + SX, methyl bromide + SX, metofluthrin + SX, metolcarb + SX, metoxadiazone + SX, mevinphos (mevinphos) + SX, Milbemectin + SX, Milbemycin oxime + SX, Monfluorothrin + SX, monocrotophos + SX, moxidectin + SX, Nared + SX, Nicotinetine ) + SX, Nicotine-Sulphate + SX, Nitenpyram (Nitenpyram) + SX, Novaluron (novaluron) + SX, Noviful Ron (noviflumuron) + SX, oil of the seeds of Chenopodium anthelminticum + SX, omethoate + SX, oxamyl (Oxamyl) + SX, oxydimeton methyl (oxydemeton-methyl) + SX, parathion (Parathion) + SX, parathion methyl (parathion-methyl) + SX, permethrin (permethrin) + SX, phenothrin (phenothrin) + SX, phenthoate + SX, phorate (phorate) + SX, phosalone (phosalone) + SX Phosmet + SX, Phosphamidon + SX, Phosphine + SX, Phoxim + SX, Pirimicarb + SX, Pirimiphos-methyl (Pirimiphos-methyl) + SX, Potassium cyanide (potassium cyanide) + SX, prallethrin + SX, profenofos (profenofos) + SX, profluthrin + SX, propargite + SX, prope Tamphos (propetamphos) + SX, propoxur + SX, propylene glycol alginate (SIP) + SX, prothiofos (prothiofos) + SX, pyflubumide + SX, pymetrozine + SX, pyraclofos (pyraclofoss ) + SX, pyrethrins + SX, pyridabens + SX, pyridalyl + SX, pyridaphenthion + SX, pyrifluquinazone + SX, pyrimidifen + SX, pyriminostorobin (Pyriminostrobin) + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos (quinalphos) + SX, resmethrin + SX, rotenone + SX, ryanodine (Ryanodine) + SX, Selamectin + SX, sigma cypermethrin + SX, silafluophene (silafl uofen) + SX, sodium borate + sodium borate + sodium borate (sodium bromide) + SX, sodium cyanide (sodium cyanide) + SX, sodium metaborate (sodium metaborate) + SX, spinetoram (spinetoram) + SX, spinosad + spinach Diclofen (Spirodiclofen) + SX, Spiromesifen (SX), Spiropidione (Spiropidion) + SX, Spirotetramat (Spirotetramat) + SX, Sulfluramid (Sulfluramid) + SX, Sulfotep (sulfotep) + SX, Sulfoxaflor (sulfofaflorol) ) + SX, sulfur + sulfur SX, sulfuryl fluoride + SX, tartar emetic + SX, tau-fluvalinate + tau SX, tebufenozide + SX, tebufenpyrade (Tebufenpyrad) + SX, tebu pirimphos (tebupirimfos) + SX, teflubenzuron (teflubenzuron) + SX, tefluthrin (tefluthrin) + SX, temephos (temephos) + SX, ter Phosphite (terbufos) + SX, terpene component extracted from Chenopodium ambrosioides L. (terpene constitue
nts of the extract of chenopodium ambrosioides near ambrosioides, Brand name: Terpenoid blend QRD 460) + SX, tetrachlorvinphos (tetrachlorovinphos) + SX, tetradiphone (tetradifon) + SX, tetramethrin (tetramethrin) + SX, tetramethylfulthrin ( tetramethylfluthrin) + SX, tetranipyrol (tetraniliprole) + SX, theta-cypermethrin (theta-cypermethrin) + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, Thiofanox + SX, Thiometon (Siometon) + SX, Thiosultap disodium salt (thiosultap-disodium) + SX, Thiosultap monosodium salt (thiosultap-monosodium) + SX, Thioxazafen (Tioxazafen) + SX, Tolfenpyrad (tolfenpyrad) + SX, tralomethrin (tralomethrin) + SX, transfluthrin (t ransfluthrin) + SX, triazamate + SX, triazophos + SX, trichlorfon (tricholfon) + SX, triflumezopyrim + SX, triflumuron + SX, trimethacarb + SX, Pyrazoflor (tyclopyrazoflor) + SX, vamidothion + SX, Shrimp oyster wood extract (wood extract of Quasisia amara) + SX, XMC (3,5-dimethylphenyl N-methylcarbamate) + SX, xylylcarb (xylylcarb) + SX, zetacipermethrin (zeta-cypermethrin) + SX, zinc phosphide (zinc phosphide) + SX, 3-bromo-N- [2,4-dichloro-6- (methylcarbamoyl) phenyl] -1- (3, 5-Dichloropyridin-2-yl) -1H-pyrazole-5-carboxamide (1104384-14-6) + SX, N- [3-chloro-1- (pyridin-3-yl) -1H-pyra 4-yl] -N-ethyl-3- (3,3,3-trifluoropropanesulfinyl) propanamide (1477923-37-7) + SX, 2- [3- (ethanesulfonyl) pyridine-2 -Yl] -5- (trifluoromethanesulfonyl) benzoxazole (1616678-32-0) + SX, 4- [5- (3,5-dichlorophenyl) -5- (trifluoromethyl) -4,5-dihydro- 1,2-oxazol-3-yl] -2-methyl-N- (1-oxothietan-3-yl) benzamide (1241050-20-3) + SX, 3-methoxy-N- (5- {5- (5- {5- (5 Trifluoromethyl) -5- [3- (trifluoromethyl) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} indan-1-yl) propanamide (1118626-57-5) + SX, N- [2-bromo-6-chloro-4- (1 1,1,1,2,3,3,3-heptafluoropropan-2-yl) phenyl] -3- {ethyl [(pyridin-4-yl) carbonyl] amino} -2-methoxybenzamide (142951-53- 0) + SX, N- [2-bromo-6-chloro-4- (1,1,1,2,3,3,3-heptafluoropropan-2-yl) phenyl] -3- [ethyl (4 -Cyanobenzoyl) amino] -2-methoxybenzamide (1609007-65-9) + SX, N- [2-bromo-6-difluoromethoxy-4- (1,1,1,2,3,3,3- Heptafluoropropan-2-yl) phenyl] -3- {methyl [(pyridin-4-yl) carbonyl] amino} -2-methoxybenzamide (1630969-78-6) + SX, 1- {2-fluoro-4 -Methyl-5-[(2,2,2-trifluoroethyl) sulfy [L] phenyl} -3- (trifluoromethyl) -1H-1,2,4-triazol-5-amine (885026-50-6) + SX, BT crop protein Cry1Ab (BT crop protein Cry1Ab) + SX, BT crop protein Cry1Ac (BT crop protein Cry1 Ac) + SX, BT crop protein Cry1Fa (BT crop protein Cry1Fa) + SX, BT crop protein Cry1A.105 (BT crop protein Cry1A.105) + SX, BT crop protein Cry2Ab (BT crop protein Cry2Ab) + SX, BT crop protein Vip3A (BT crop protein Vip3A) + SX, BT crop protein mCry3A (BT crop protein Cry3A) + SX, BT crop protein Cry3Ab (BT crop protein Cry3Ab) + SX, BT crop protein Cry3Bb (BT crop protein Cry3Bb) + SX, BT crop protein Cry34Ab1 / Cry35Ab1 (BT crop protein Cry34Ab1 / Cry35Ab1) + SX, Adoxophys orana granulosis virus) + SX, anti Karsia ・ Gematalis nuclear polyhedrosis disease (Anticarsia gemmatalis mNPV) + SX, Autographa california nuclear polyhedrosis virus FV # 11 (Autographa californica mNPV FV # 11) + SX, S. pomonella granulosa virus V15 (Cydia pomonella GV V 15) + SX, S. s. Pomonella granule disease virus V22 (Cydia pomonella GV V22) + SX, Cryptofrebbia leukotleta granule disease virus (Cryptophlebia leucotreta GV) + SX, Dendolimus punctatus cytoplasmic polyhedron virus (Dendrolimus punctatus cypovirus) + SX, Helicoverpa armigera nucleus polygonia Body disease virus BV-0003 strain (Helicoverpa armigera NPV BV-0003) + SX, Helicoverpa zea nuclear polyhedrosis virus (Helicoverpa zea NPV) + SX, Lymantria dispar nuclear polyhedrosis virus (Lymantria dispar NPV) + SX, Mamestra ・ Brassicae nuclear polyhedrosis virus (Mamestra brassicae NPV) + SX, Mamestra ・ configurata nuclear polyhedrosis virus (Mamestra configurata NPV) + SX, Neodiplion abientis nuclear polyhedrosis virus (Neodiprion abietis NPV) + SX, Neodiplion reconta nuclear polyhedrosis virus (Neodiprion lecontei NPV) + SX, Neodiprion sertifer nuclear polygon Body disease virus (Neodiprion sertifer NPV) + SX, Nosema locustae (Nosema locustae) + SX, Orgiia pseudotsudatsu nuclear polyhedrosis virus (Orgyia pseudotsugata NPV) + SX, Pieris rapae disease virus (Pieris rapae GV) + SX Plodia interpunctella granulosis virus (Plodia interpunctella GV) + SX, Spodoptera exigua nuclear polyhedrosis virus (Spodoptera exigua mNPV) + SX, Spodoptera littoralis nuclear polyhedrosis virus (Spodoptera littoralis mNPV) + SX, Spodoptera・ Ritula nuclear polyhedrosis virus (Spodoptera litura NPV) + SX, Ars Robotris ・ Dactyloides (Arthrobo trys dactyloides) + SX, Bacillus films GB-126 strain (Bacillus firmus GB-126) + SX, Bacillus films I-1582 strain (Bacillus firmus I-1582) + SX, Bacillus megaterium + SX, Bacillus sp. Strain AQ175 (Bacillus sp. AQ175) + SX, Bacillus sp. Strain AQ 177 (Bacillus sp. AQ 177) + SX, Bacillus sp. Strain AQ 178 (Bacillus sp. AQ 178) + SX, Bacillus sphaericus 2362 (Bacillus sphaericus 2362) + SX, Bacillus sphaericus ABTS 1743 (Bacillus sphaericus ABTS 1743) + SX, Bacillus sphaericus Serotype H 5a 5 b (Bacillus sphaericus Serotype H 5 a 5 b) + SX, Bacillus thuringiensis AQ 52 strain (Bacillus thuringiensis AQ 52) + SX, Thuringiensis strain BD # 32 (Bacillus thuringiensis BD # 32) + SX, Bacillus thuringiensis strain CR-371 (Bacillus thuringiensis CR-371) + SX, Bacillus thuringiensis. 57 strains (Bacillus thuringiensis subsp. Aizawai ABTS-1857) + SX, Bacillus thuringiensis subspecies AM65-52 strain (Bacillus thuringiensis subsp. Aizawai AM65-52) + SX, Bacillus thuringiensis subd species GC- 91 strains (Bacillus thuringiensis subsp. Aizawai GC-91) + SX, Bacillus thuringiensis subspecies Serotype H-7 strain (Bacillus thuringiensis subsp. Aizawai Serotype H-7) + SX, Bacillus thuringiensis cristerchi subspecies ABTS 351 strain (Bacillus thuringiensis subsp. Kurstaki ABTS 351) + SX, Bacillus thuringiensis ・ chrysantice subsp. BMP 123 strain (Bacillus thuringiensis subsp. Kurstaki BMP 123) + SX, Bacillus thuringiensis ・ crista chia sp. EG234 (Bacillus thuringiensis subsp. Kurstaki EG234) + SX, Bacillus thuringiensis cristae subsp. EG7841 strain (Bacillus thuringiensis subsp. Kurstaki EG7841 +) SX, Bacillus thuringiensis cristaea subsp. EVB 113-19 (Bacillus thuringiensis subsp. Kurstaki EVB 113-19) + SX, Bacillus thuringiensis cristae subsp. F 810 (Bacillus thuringiensis subsp. Kurstaki F 810) + SX, Bacillus thuringiensis cristaea subsp. HD-1 strain (Bacillus thuringiensis subsp. Kurstaki HD-1) + SX, Bacillus thuringiensis cristae subsp. Strain PB54 (Bacillus thuringiensis subsp. Kurstaki PB54) + SX, Bacillus thuringiensis・ Christeraki subspecies strain SA-11 (Bacillus thuringiensis subsp. Kurstaki SA-11) + SX, Bacillus thuringiensis ・ Christase strain subspecies SA-12 (Bacillus thuringiensis subsp. Kurstaki SA-12) + SX, Bacillus thuringiensis・ B. thuringiensis subsp. Strain NB176 (Bacillus thuringiensis subsp. Tenebriosis NB176) + SX, Bacillus thuringiensis ・ Chu Ringing cis subsp. Strain MPPL 002 (Bacillus thuringiensis subsp. Thuringiensis MPPL 002) + SX, Bacillus thuringiensis subsp. Morrisoni subsp. Strain (Bacillus thuringiensis subsp. Morrisoni) + SX, Bacillus thuringiensis col. SX, Bacillus thuringiensis dermstasis variant 24-91 (Bacillus thuringiensis var. Darmstadiensis 24-91) + SX, Bacillus thuringiensis dendolimus variant (Bacillus thuringiensis var. Dendrolimus) + SX, Bacillus thuringiensis Cis galleria variant strain (Bacillus thuringiensis var. Galleriae) + SX, Bacillus thuringiensis isra elensis variant BMP 144 strain (Bacillus thuringiensis var. Israelensis BMP 144) + SX, Bacillus thuringiensis isla elensis variant serotype H-14 strain (Bacillus thuringiensis var. Israelensis serotyp eH-14) + SX, Bacillus thuringiensis japonensis variant buibui strain (Bacillus thuringiensis var. japonensis buibui) + SX, Bacillus thuringiensis San Diego variant M-7 strain (Bacillus thuringiensis var. san diego M-7) + SX, Bacillus thuringiensis-7216 variant (Bacillus thuringiensis var. 7216) + SX, Bacillus thuringiensis-aegypti variant (Bacillus thuringiensis var. Aegypti) + SX, Bacillus thuringiensis-T36 variant (Bacillus thuringiensis var) .T36) + SX, Beauberia basiana ANT-03 strain (Beauvelia bassiana ANT-03) + SX, Beauberia basiana strain ATCC 74040 (Beauvelia bassiana ATCC 74040) + SX, Beauberia basiana strain GHA (Beauvelia bassiana GHA) + SX, bovelia・ Bronniati (Beauveria brongniartii) + SX, Burkholderia lignensis A 396 strain (Burkholderia rinojensis A 396) + SX, Chromobacteria suborbitum PRAA4-1T strain (Chromobacterium subtsugae PRAA4-1T) + SX, Dactylella ellipsospora + SX, Dectylaria thaumasia + SX, Hilstera minesose sis・ Rossiliens (Hirsutella rhossiliensis) + SX, Hirstela thompsoni (Hirsutella thompsonii) + SX, Lagenidium giganteum + SX, Recanicillium ・ Lecani KV 01 (Lecanicillium lecanii KV 01) + SX, SX Conidia (Lecanicillium lecanii conidia of strain DAOM198499) + SX, conidia (Lecanicillium lecanii conidia of strain DAOM 216596) + SX, Metallidium anisopriae F 52 strain (Metarhizium anisopliae F54) Variant strain (Metarhizium anisopliae var. Acridum) + SX, Metarhizium-Furabobiride (Metarhizium flavoviride) + SX, Mona Kurosupo helium-Fimatopagamu (Monacrosporium phymatopagum) + SX,
P. periomyces fumosoroseus Apopka 97 strain (Paecilomyces fumosoroseus Apopka 97) + SX, P. pelyomyces lilacinasis 251 strain (Paecilomyces lilacinus 251) + SX, P. pelyomyces tenuipes T1 strain (Paecilomyces tenuipes T1) + SX・ Nishizawae Pn1 strain (Pasteuria nishizawae Pn1) + SX, Pasteuria penetrans (Pasteuria penetrans) + SX, Pasteuria usgae (Pasteuria usgae) + SX, Pasteuria toynei (Pasteuria thoynei) + SX, Serratia entomophila + SX, Verticillium chlamydosporium (Verticillium chlamydosporium) + SX, Verticillium lecani strain NCIM 1312 (Verticillium lecani NCIM 1312) + SX.
上記群（ｂ）の本成分と本発明化合物との組み合わせ：
　アシベンゾラルSメチル（acibenzolar-S-methyl）+SX、アルジモルフ（aldimorph）+SX、アメトクトラジン（ametoctradin）+SX、アミノピリフェン(aminopyrifen)+SX、アミスルブロム（amisulbrom）+SX、アニラジン（anilazine）+SX、アザコナゾール（azaconazole）+SX、アゾキシストロビン（azoxystrobin）+SX、塩基性硫酸銅（basic copper sulfate）+SX、ベナラキシル（benalaxyl）+SX、ベナラキシルM（benalaxyl-M）+SX、ベノダニル（benodanil）+SX、ベノミル（benomyl）+SX、ベンチアバリカルブ（benthiavalicarb）+SX、ベンチアバリカルブイソプロピル（benthivalicarb-isopropyl）+SX、ベンゾビンジフルピル（benzovindiflupyr）+SX、ビナパクリル（binapacryl）+SX、ビフェニル（biphenyl）+SX、ビテルタノール（bitertanol）+SX、ビキサフェン（bixafen）+SX、ブラストサイジンS（blasticidin-S）+SX、ボルドー液（Bordeaux mixture）+SX、ボスカリド（boscalid）+SX、ブロモタロニル（bromothalonil）+SX、ブロムコナゾール（bromuconazole）+SX、ブピリメート（bupirimate）+SX、キャプタホール（captafol）+SX、キャプタン（captan）+SX、カルベンダジム（carbendazim）+SX、カルボキシン（carboxin）+SX、カルプロパミド（carpropamid）+SX、キノメチオナート（chinomethionat）+SX、キチン（chitin）+SX、クロロネブ（chloroneb）+SX、クロロタロニル（chlorothalonil）+SX、クロゾリネート（chlozolinate）+SX、コレトクロリンＢ（colletochlorin B）+SX、酢酸銅(II)（copper(II) acetate）+SX、水酸化銅(II)（copper(II) hydroxide）+SX、塩基性塩化銅（copper oxychloride）+SX、硫酸銅(II)（copper(II) sulfate）+SX、クモキシストロビン（coumoxystrobin）+SX、シアゾファミド（cyazofamid）+SX、シフルフェナミド（cyflufenamid）+SX、シモキサニル（cymoxanil）+SX、シプロコナゾール（cyproconazole）+SX、シプロジニル（cyprodinil）+SX、ジクロベンチアゾクス（dichlobentiazox）+SX、ジクロフルアニド（dichlofluanid）+SX、ジクロシメット（diclocymet）+SX、ジクロメジン（diclomezine）+SX、ジクロラン（dicloran）+SX、ジエトフェンカルブ（diethofencarb）+SX、ジフェノコナゾール（difenoconazole）+SX、ジフルメトリム（diflumetorim）+SX、ジメタクロン（dimethachlone）+SX、ジメチリモール（dimethirimol）+SX、ジメトモルフ（dimethomorph）+SX、ジモキシストロビン（dimoxystrobin）+SX、ジニコナゾール（diniconazole）+SX、ジニコナゾールM（diniconazole－M）+SX、ジノカップ（dinocap）+SX、ジピメティトロン（dipymetitrone）+SX、ジチアノン（dithianon）+SX、ドデシルベンゼンスルホン酸ビスエチレンジアミン銅(II)錯塩（dodecylbenzenesulphonic acid bisethylenediamine　copper(II) salt）+SX、ドデモルフ（dodemorph）+SX、ドジン（dodine）+SX、エジフェンホス（edifenphos）+SX、エノキサストロビン（enoxastrobin）+SX、エポキシコナゾール（epoxiconazole）+SX、エタコナゾール（etaconazole）+SX、エタボキサム（ethaboxam）+SX、エチリモール（ethirimol）+SX、エトリジアゾール（etridiazole）+SX、ティーツリー抽出物（extract from Melaleuca alternifolia）+SX、オオイタドリ抽出物（extract from Reynoutria sachalinensis）+SX、ハウチワマメ苗木の子葉からの抽出物（extract from the cotyledons of lupine plantlets("BLAD”)）+SX、ニンニク抽出成分（extract of Allium sativum）+SX、スギナ抽出成分（extract of Equisetum arvense）+SX、キンレンカ抽出成分（extract of Tropaeolum majus）+SX、ファモキサドン（famoxadone）+SX、フェンアミドン（fenamidone）+SX、フェナミンストロビン（fenaminstrobin）+SX、フェナリモル（fenarimol）+SX、フェンブコナゾール（fenbuconazole）+SX、フェンフラム（fenfuram）+SX、フェンヘキサミド（fenhexamid）+SX、フェノキサニル（fenoxanil）+SX、フェンピクロニル（fenpiclonil）+SX、フェンピコキサミド（fenpicoxamid）+SX、フェンプロピジン（fenpropidin）+SX、フェンプロピモルフ（fenpropimorph）+SX、フェンピラザミン（fenpyrazamine）+SX、酢酸トリフェニル錫（fentin acetate）+SX、塩化トリフェニル錫（fentin chloride）+SX、水酸化トリフェニル錫（fentin hydroxide）+SX、フェルバム（ferbam）+SX、フェリムゾン（ferimzone）+SX、フロリルピコキサミド（florylpicoxamid）+SX、フルアジナム（fluazinam）+SX、フルジオキソニル（fludioxonil）+SX、フルフェノキシストロビン（flufenoxystrobin）+SX、フルインダピル（fluindapyr）+SX、フルモルフ（flumorph）+SX、フルオピコリド（fluopicolide）+SX、フルオピモミド（fluopimomide）+SX、フルオルイミド（fluoroimide）+SX、フルオキサストロビン（fluoxastrobin）+SX、フルキンコナゾール（fluquinconazole）+SX、フルシラゾール（flusilazole）+SX、フルスルファミド（flusulfamide）+SX、フルチアニル（flutianil）+SX、フルトラニル（flutolanil）+SX、フルトリアホール（flutriafol）+SX、フルキサピロキサド（fluxapyroxad）+SX、ホルペット（folpet）+SX、ホセチル（fosetyl）+SX、ホセチルアルミニウム（fosetyl-aluminium）+SX、フベリダゾール（fuberidazole）+SX、フララキシル（furalaxyl）+SX、フラメトピル（furametpyr）+SX、グアザチン（guazatine）+SX、ヘキサコナゾール（hexaconazole）+SX、ヒメキサゾール（hymexazole）+SX、イマザリル（imazalil）+SX、イミベンコナゾール（imibenconazole）+SX、イミノクタジン（iminoctadine）+SX、イミノクタジン三酢酸塩（iminoctadine triacetate）+SX、ヨードカルブ（iodocarb）+SX、イプコナゾール（ipconazole）+SX、イプフェントリフルコナゾール（ipfentrifluconazole）+SX、イプフルフェノキン（ipflufenoquin）+SX、イプロベンホス（iprobenfos）+SX、イプロジオン（iprodione）+SX、イプロバリカルブ（iprovalicarb）+SX、イソフェタミド（isofetamid）+SX、イソフルシプラム（isoflucypram）+SX、イソプロチオラン（isoprothiolane）+SX、イソピラザム（isopyrazam）+SX、イソチアニル（isotianil）+SX、カスガマイシン（kasugamycin）+SX、クレソキシムメチル（kresoxim-methyl）+SX、ラミナリン（laminarin）+SX、オークの葉及び樹皮（leaves and bark of Quercus）+SX、マンコゼブ（mancozeb）+SX、マンデストロビン（mandestrobin）+SX、マンジプロパミド（mandipropamid）+SX、マンネブ（maneb）+SX、メフェントリフルコナゾール（mefentrifluconazole）+SX、メパニピリム（mepanipyrim）+SX、メプロニル（mepronil）+SX、メプチルジノカップ（meptyldinocap）+SX、メタラキシル（metalaxyl）+SX、メタラキシルM（metalaxyl-M）+SX、メトコナゾール（metconazole）+SX、メタスルホカルブ（methasulfocarb）+SX、メチラム（metiram）+SX、メトミノストロビン（metominostrobin）+SX、メトラフェノン（metrafenone）+SX、マシン油（mineral oils）+SX、ミクロブタニル（myclobutanil）+SX、ナフチフィン（naftifine）+SX、ニーム油（neem oil）+SX、ヌアリモール（nuarimol）+SX、オクチリノン（octhilinone）+SX、オフラセ（ofurace）+SX、オリサストロビン（orysastrobin）+SX、オキサジキシル（oxadixyl）+SX、オキサチアピプロリン（oxathiapiprolin）+SX、oxine-copper+SX、オキソリニック酸（oxolinic acid）+SX、オキスポコナゾール（oxpoconazole）+SX、オキスポコナゾールフマル酸塩（oxpoconazole fumarate）+SX、オキシカルボキシン（oxycarboxin）+SX、オキシテトラサイクリン（oxytetracycline）+SX、ペフラゾエート（pefurazoate）+SX、ペンコナゾール（penconazole）+SX、ペンシクロン（pencycuron）+SX、ペンフルフェン（penflufen）+SX、ペンチオピラド（penthiopyrad）+SX、フェナマクリル（phenamacril）+SX、亜リン酸（phosphorous acid）+SX、フサライド（phthalide）+SX、ピカルブトラゾクス（picarbutrazox）+SX、ピコキシストロビン（picoxystrobin）+SX、ピペラリン（piperalin）+SX、ポリオキシン（polyoxins）+SX、炭酸水素カリウム（potassium hydrogencarbonate）+SX、亜リン酸二水素カリウム（potassium dihydrogenphosphite）+SX、プロベナゾール（probenazole）+SX、プロクロラズ（prochloraz）+SX、プロシミドン（procymidone）+SX、プロパミジン（propamidine）+SX、プロパモカルブ（propamocarb）+SX、プロピコナゾール（propiconazole）+SX、プロピネブ（propineb）+SX、プロキナジド（proquinazid）+SX、プロチオカルブ（prothiocarb）+SX、プロチオコナゾール（prothioconazole）+SX、ピジフルメトフェン（pydiflumetofen）+SX、ピラクロストロビン（pyraclostrobin）+SX、ピラメトストロビン（pyrametostrobin）+SX、ピラオキシストロビン（pyraoxystrobin）+SX、ピラプロポイン（pyrapropoyne）+SX、ピラジフルミド（pyraziflumid）+SX、ピラゾホス（pyrazophos）+SX、ピリベンカルブ（pyribencarb）+SX、ピリブチカルブ（pyributicarb）+SX、ピリフェノックス（pyrifenox）+SX、ピリメタニル（pyrimethanil）+SX、ピリモルフ（pyrimorph）+SX、ピリオフェノン（pyriofenone）+SX、ピリソキサゾール（pyrisoxazole）+SX、ピロキロン（pyroquilon）+SX、キラヤ科植物抽出成分（Quillaja extract）+SX、キンコナゾール（quinconazole）+SX、キノフメリン（quinofumelin）+SX、キノキシフェン（quinoxyfen）+SX、キントゼン（quintozene）+SX、キヌアのサポニン（Saponins of Chenopodium quinoa）+SX、セダキサン（sedaxane）+SX、シルチオファム（silthiofam）+SX、シメコナゾール（simeconazole）+SX、炭酸水素ナトリウム（sodium hydrogencarbonate）+SX、スピロキサミン（spiroxamine）+SX、ストレプトマイシン（streptomycin）+SX、硫黄（sulfur）+SX、テブコナゾール（tebuconazole）+SX、テブフロキン（tebufloquin）+SX、テクロフタラム（teclofthalam）+SX、テクナゼン（tecnazene）+SX、テルビナフィン（terbinafine）+SX、テトラコナゾール（tetraconazole）+SX、チアベンダゾール（thiabendazole）+SX、チフルザミド（thifluzamide）+SX、チオファネート（thiophanate）+SX、チオファネートメチル（thiophanate-methyl）+SX、チウラム（thiram）+SX、チモール（thymol）+SX、チアジニル（tiadinil）+SX、トルクロホスメチル（tolclofos-methyl）+SX、トルフェンピラド（tolfenpyrad）+SX、トルプロカルブ（tolprocarb）+SX、トリルフルアニド（tolylfluanid）+SX、トリアジメホン（triadimefon）+SX、トリアジメノール（triadimenol）+SX、トリアゾキシド（triazoxide）+SX、トリクロピリカルブ（triclopyricarb）+SX、トリシクラゾール（tricyclazole）+SX、トリデモルフ（tridemorph）+SX、トリフロキシストロビン（trifloxystrobin）+SX、トリフルミゾール（triflumizole）+SX、トリホリン（triforine）+SX、トリチコナゾール（triticonazole）+SX、バリダマイシン（validamycin）+SX、バリフェナレート（valifenalate）+SX、ビンクロゾリン（vinclozolin）+SX、マスタードパウダー（yellow mustard powder）+SX、zinc thiazole+SX、ジネブ（zineb）+SX、ジラム（ziram）+SX、ゾキサミド（zoxamide）+SX、３－（ジフルオロメチル）－Ｎ－メトキシ－１－メチル－Ｎ－［（１Ｒ）－１－メチル－２－（２，４，６－トリクロロフェニル）エチル］ピラゾール－４－カルボキサミド（1639015-48-7）+SX、３－（ジフルオロメチル）－Ｎ－メトキシ－１－メチル－Ｎ－［（１Ｓ）－１－メチル－２－（２，４，６－トリクロロフェニル）エチル］ピラゾール－４－カルボキサミド（1639015-49-8）+SX、３－（ジフルオロメチル）－１－メチル－Ｎ－（１，１，３－トリメチルインダン－４－イル）ピラゾール－４－カルボキサミド（141573-94-6）+SX、３－（ジフルオロメチル）－１－メチル－Ｎ－［（３Ｒ）－１，１，３－トリメチルインダン－４－イル］ピラゾール－４－カルボキサミド（1352994-67-2）+SX、３－（ジフルオロメチル）－Ｎ－［（３Ｒ）－７－フルオロ－１，１，３－トリメチルインダン－４－イル］－１－メチルピラゾール－４－カルボキサミド（1513466-73-3）+SX、３－クロロ－５－フェニル－６
－メチル－４－（２，６－ジフルオロフェニル）ピリダジン（1358061-55-8）+SX、Ｎ’－［４－（｛３－［（４－クロロフェニル）メチル］－１，２，４－チアジアゾール－５－イル｝オキシ）－２，５－ジメチルフェニル］－Ｎ－エチル－Ｎ－メチルメタンイミドアミド（1202781-91-6）+SX、２－｛３－［２－（１－｛［３，５－ビス（ジフルオロメチル）－１H－ピラゾール－１－イル］アセチル｝ピペリジン－４－イル）－１，３－チアゾール－４－イル］－４，５－ジヒドロ－１，２－オキサゾール－５－イル｝－３－クロロフェニル＝メタンスルホナ－ト（1360819-11-9）+SX、４－（２－ブロモ－４－フルオロフェニル）－N－（２－クロロ－６－フルオロフェニル）－１，３－ジメチル－１Ｈ－ピラゾール－５－アミン（1362477-26-6）+SX、２,２－ジメチル－９－フルオロ－５－（キノリン－３－イル）－２,３－ジヒドロベンゾ［ｆ］［１，４］オキサゼピン（1207749-50-5）+SX、２－［６－（３－フルオロ－４－メトキシフェニル）－５－メチルピリジン－２－イル］キナゾリン（1257056-97-5）+SX、５－フルオロ－２－［（４－メチルフェニル）メトキシ］－４－ピリミジンアミン（1174376-25-0）+SX、５－フルオロ－４－イミノ－３－メチル－１－トシル－３，４－ジヒドロピリミジン－２（１Ｈ）－オン（1616664-98-2）+SX、Ｎ’－（２，５－ジメチル－４－フェノキシフェニル）－Ｎ－エチル－Ｎ－メチルメタンイミドアミド（1052688-31-9）+SX、Ｎ’－｛４－［（４，５－ジクロロチアゾール－２－イル）オキシ］－２，５－ジメチルフェニル｝－Ｎ－エチル－Ｎ－メチルメタンイミドアミド（929908-57-6）+SX、（２Ｚ）－３－アミノ－２－シアノ－３－フェニルアクリル酸エチル（39491-78-6）+SX、Ｎ－［（２－クロロチアゾール－５－イル）メチル］－Ｎ－エチル－６－メトキシ－３－ニトロピリジン－２－アミン（1446247-98-8）+SX、１－［２－（｛［１－（４－クロロフェニル）－１Ｈ－ピラゾール－３－イル］オキシ｝メチル）－３－メチルフェニル］－４－メチル－５－オキソ－４，５－ジヒドロ－１Ｈ－テトラゾール（1472649-01-6）+SX、α－［３－（４－クロロ－２－フルオロフェニル）－５－（２，４－ジフルオロフェニル）－４－イソキサゾリル］－３－ピリジンメタノール（1229605-96-2）+SX、（αＳ）－［３－（４－クロロ－２－フルオロフェニル）－５－（２，４－ジフルオロフェニル）－４－イソキサゾリル］－３－ピリジンメタノール（1229606-46-5）+SX、（αＲ）－［３－（４－クロロ－２－フルオロフェニル）－５－（２，４－ジフルオロフェニル）－４－イソキサゾリル］－３－ピリジンメタノール（1229606-02-3）+SX、２－｛［３－（２－クロロフェニル）－２－（２，４－ジフルオロフェニル）オキシラン－２－イル］メチル｝－２，４－ジヒドロ－３Ｈ－１，２，４－トリアゾール－３－チオン（1342260-19-8）+SX、２－｛［（２Ｒ，３Ｓ）－３－（２－クロロフェニル）－２－（２，４－ジフルオロフェニル）オキシラン－２－イル］メチル｝－２，４－ジヒドロ－３Ｈ－１，２，４－トリアゾール－３－チオン（1638897-70-7）+SX、２－｛［（２Ｓ，３Ｒ）－３－（２－クロロフェニル）－２－（２，４－ジフルオロフェニル）オキシラン－２－イル］メチル｝－２，４－ジヒドロ－３Ｈ－１，２，４－トリアゾール－３－チオン（1638897-71-8）+SX、２－｛［（２Ｒ，３Ｒ）－３－（２－クロロフェニル）－２－（２，４－ジフルオロフェニル）オキシラン－２－イル］メチル｝－２，４－ジヒドロ－３Ｈ－１，２，４－トリアゾール－３－チオン（1638897-72-9）+SX、２－｛［（２Ｓ，３Ｓ）－３－（２－クロロフェニル）－２－（２，４－ジフルオロフェニル）オキシラン－２－イル］メチル｝－２，４－ジヒドロ－３Ｈ－１，２，４－トリアゾール－３－チオン（1638897-73-0）+SX、１－｛［３－（２－クロロフェニル）－２－（２，４－ジフルオロフェニル）オキシラン－２－イル］メチル｝－１Ｈ－１，２，４－トリアゾール－５－イル　チオシアナト（1342260-26-7）+SX、１－｛［（２Ｒ，３Ｓ）－３－（２－クロロフェニル）－２－（２，４－ジフルオロフェニル）オキシラン－２－イル］メチル｝－１Ｈ－１，２，４－トリアゾール－５－イル　チオシアナト（1638897-82-1）+SX、１－｛［（２Ｓ，３Ｒ）－３－（２－クロロフェニル）－２－（２，４－ジフルオロフェニル）オキシラン－２－イル］メチル｝－１Ｈ－１，２，４－トリアゾール－５－イル　チオシアナト（1638897-84-3）+SX、１－｛［（２Ｒ，３Ｒ）－３－（２－クロロフェニル）－２－（２，４－ジフルオロフェニル）オキシラン－２－イル］メチル｝－１Ｈ－１，２，４－トリアゾール－５－イル　チオシアナト（1638897-86-5）+SX、１－｛［（２Ｓ，３Ｓ）－３－（２－クロロフェニル）－２－（２，４－ジフルオロフェニル）オキシラン－２－イル］メチル｝－１Ｈ－１，２，４－トリアゾール－５－イル　チオシアナト（1638897-89-8）+SX、５－（４－クロロベンジル）－２－クロロメチル－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1394057-11-4）+SX、（１Ｒ，２Ｓ，５Ｓ）－５－（４－クロロベンジル）－２－クロロメチル－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1801930-06-2）+SX、（１Ｓ，２Ｒ，５Ｒ）－５－（４－クロロベンジル）－２－クロロメチル－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1801930-07-3）+SX、（１Ｒ，２Ｒ，５Ｒ）－５－（４－クロロベンジル）－２－クロロメチル－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1801919-53-8）+SX、（１Ｓ，２Ｓ，５Ｓ）－５－（４－クロロベンジル）－２－クロロメチル－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1801919-54-9）+SX、（１Ｒ，２Ｒ，５Ｓ）－５－（４－クロロベンジル）－２－クロロメチル－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1801919-55-0）+SX、（１Ｓ，２Ｓ，５Ｒ）－５－（４－クロロベンジル）－２－クロロメチル－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1801919-56-1）+SX、（１Ｒ，２Ｓ，５Ｒ）－５－（４－クロロベンジル）－２－クロロメチル－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1801919-57-2）+SX、（１Ｓ，２Ｒ，５Ｓ）－５－（４－クロロベンジル）－２－クロロメチル－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1801919-58-3）+SX、メチル＝３－［（４－クロロフェニル）メチル］－２－ヒドロキシ－１－メチル－２－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタンカルボキシラート（1791398-02-1）+SX、メチル＝（１Ｒ，２Ｓ，３Ｓ）－３－［（４－クロロフェニル）メチル］－２－ヒドロキシ－１－メチル－２－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタンカルボキシラート+SX、メチル＝（１Ｓ，２Ｒ，３Ｒ）－３－［（４－クロロフェニル）メチル］－２－ヒドロキシ－１－メチル－２－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタンカルボキシラート+SX、メチル＝（１Ｒ，２Ｒ，３Ｒ）－３－［（４－クロロフェニル）メチル］－２－ヒドロキシ－１－メチル－２－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタンカルボキシラート+SX、メチル＝（１Ｓ，２Ｓ，３Ｓ）－３－［（４－クロロフェニル）メチル］－２－ヒドロキシ－１－メチル－２－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタンカルボキシラート+SX、メチル＝（１Ｒ，２Ｒ，３Ｓ）－３－［（４－クロロフェニル）メチル］－２－ヒドロキシ－１－メチル－２－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタンカルボキシラート+SX、メチル＝（１Ｓ，２Ｓ，３Ｒ）－３－［（４－クロロフェニル）メチル］－２－ヒドロキシ－１－メチル－２－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタンカルボキシラート+SX、メチル＝（１Ｒ，２Ｓ，３Ｒ）－３－［（４－クロロフェニル）メチル］－２－ヒドロキシ－１－メチル－２－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタンカルボキシラート+SX、メチル＝（１Ｓ，２Ｒ，３Ｓ）－３－［（４－クロロフェニル）メチル］－２－ヒドロキシ－１－メチル－２－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタンカルボキシラート+SX、２－クロロメチル－５－（４－フルオロベンジル）－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1394057-13-6）+SX、（１Ｒ，２Ｓ，５Ｓ）－２－クロロメチル－５－（４－フルオロベンジル）－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1801930-08-4）+SX、（１Ｓ，２Ｒ，５Ｒ）－２－クロロメチル－５－（４－フルオロベンジル）－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1801930-09-5）+SX、（１Ｒ，２Ｒ，５Ｒ）－２－クロロメチル－５－（４－フルオロベンジル）－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1638898-08-4）+SX、（１Ｓ，２Ｓ，５Ｓ）－２－クロロメチル－５－（４－フルオロベンジル）－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1638898-10-8）+SX、（１Ｒ，２Ｒ，５Ｓ）－２－クロロメチル－５－（４－フルオロベンジル）－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1638898-13-1）+SX、（１Ｓ，２Ｓ，５Ｒ）－２－クロロメチル－５－（４－フルオロベンジル）－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1638898-16-4）+SX、（１Ｒ，２Ｓ，５Ｒ）－２－クロロメチル－５－（４－フルオロベンジル）－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1638898-20-0）+SX、（１Ｓ，２Ｒ，５Ｓ）－２－クロロメチル－５－（４－フルオロベンジル）－２－メチル－１－（１Ｈ－１，２，４－トリアゾール－１－イルメチル）シクロペンタノール（1638898-24-4）+SX、（Ｒ）－２－［２－クロロ－４－（４－クロロフェノキシ）フェニル］－１－（１，２，４－トリアゾール－１－イル）ペント－３－イン－２－オール（1801919-59-4）+SX、（Ｒ）－２－［４－（４－クロロフェノキシ）－２－（トリフルオロメチル）フェニル］－１－（１，２，４－トリアゾール－１－イル）プロパン－２－オール（1616236-94-2）+SX、（Ｒ）－１－［４－（４－クロロフェノキシ）－２－（トリフルオロメチル）フェニル］－１－シクロプロピル－２－（１，２，４－トリアゾール－１－イル）エタノール（1801919-60-7）+SX、（Ｒ）－２－［４－（４－クロロフェノキシ）－２－（トリフルオロメチル）フェニル］－３－メチル－１－（１，２，４－トリアゾール－１－イル）ブタン－２－オール（1801919-61-8）+SX、３－［５－（４－クロロフェニル）－２，３－ジメチル－１，２－オキサゾリジン－３－イル］ピリジン（847749-37-5）+SX、
アグロバクテリウム・ラジオバクターK1026株（Agrobacterium radiobactor K1026）+SX、アグロバクテリウム・ラジオバクターK84株（Agrobacterium radiobactor K84）+SX、バチルス・アミロリケファシエンスAT332株（Bacillus amyloliquefaciens AT332）+SX、バチルス・アミロリケファシエンスB3株（Bacillus amyloliquefaciens B3）+SX、バチルス・アミロリケファシエンスD747株（Bacillus amyloliquefaciens D747）+SX、バチルス・アミロリケファシエンスDB101株（Bacillus amyloliquefaciens DB101）+SX、バチルス・アミロリケファシエンスDB102株（Bacillus amyloliquefaciens DB102）+SX、バチルス・アミロリケファシエンスGB03株（Bacillus amyloliquefaciens GB03）+SX、バチルス・アミロリケファシエンスFZB24株（Bacillus amyloliquefaciens FZB24）+SX、バチルス・アミロリケファシエンスFZB42株（Bacillus amyloliquefaciens FZB42）+SX、バチルス・アミロリケファシエンスIN937a株（Bacillus amyloliquefaciens IN937a）+SX、バチルス・アミロリケファシエンスMBI600株（Bacillus amyloliquefaciens MBI600）+SX、バチルス・アミロリケファシエンスQST713株（Bacillus amyloliquefaciens QST713）+SX、バチルス・アミロリケファシエンス分離株B246株（Bacillus amyloliquefaciens isolate B246）+SX、バチルス・アミロリケファシエンスF727株（Bacillus amyloliquefaciens F727）+SX、バチルス・リケニホルミスHB-2株（Bacillus licheniformis HB-2）+SX、バチルス・リケニホルミスSB3086株（Bacillus licheniformis SB3086）+SX、バチルス・プミルスAQ717株（Bacillus pumilus AQ717）+SX、バチルス・プミルスBUF-33株（Bacillus pumilus BUF-33）+SX、バチルス・プミルスGB34株（Bacillus pumilus GB34）+SX、バチルス・プミルスQST2808株（Bacillus pumilus QST2808）+SX、バチルス・シンプレクスCGF2856株（Bacillus simplex CGF2856）+SX、バチルス・スブチリス AQ153株（Bacillus subtilis AQ153）+SX、バチルス・スブチリス AQ743株（Bacillus subtilis AQ743）+SX、バチルス・スブチリスBU1814株（Bacillus subtilis BU1814）+SX、バチルス・スブチリス D747株（Bacillus subtilis D747）+SX、バチルス・スブチリス DB101株（Bacillus subtilis DB101）+SX、バチルス・スブチリスFZB24株（Bacillus subtilis FZB24）+SX、バチルス・スブチリス GB03株（Bacillus subtilis GB03）+SX、バチルス・スブチリス HAI0404株（Bacillus subtilis HAI0404）+SX、バチルス・スブチリスIAB/BS03株（Bacillus subtilis IAB/BS03）+SX、バチルス・スブチリス MBI600株（Bacillus subtilis MBI600）+SX、バチルス・スブチリス QST30002/AQ30002株（Bacillus subtilis QST30002/AQ30002）+SX、バチルス・スブチリス QST30004/AQ30004株（Bacillus subtilis QST30004/AQ30004）+SX、バチルス・スブチリス QST713株（Bacillus subtilis QST713）+SX、バチルス・スブチリス QST714株（Bacillus subtilis QST714）+SX、バチルス・スブチリス var.アミロリクエファシエンスFZB24株（Bacillus subtilis var. Amyloliquefaciens FZB24）+SX、バチルス・スブチリス Y1336株（Bacillus subtilis Y1336）+SX、バークホルデリア・セパシア（Burkholderia cepacia）+SX、バークホルデリア・セパシア・ウィスコンシン型J82株（Burkholderia cepacia type Wisconsin J82）+SX、バークホルデリア・セパシア・ウィスコンシン型M54株（Burkholderia cepacia type Wisconsin M54）+SX、カンジダ・オレオフィラO株（Candida oleophila O）+SX、カンジダ・サイトアナ（Candida saitoana）+SX、ケトミウム・クプレウム（Chaetomium cupreum）+SX、クロノスタキス・ロゼア（Clonostachys rosea）+SX、コニオシリウム・ミニタンスCGMCC8325株（Coniothyrium minitans CGMCC8325）+SX、コニオシリウム・ミニタンスCON/M/91-8株（Coniothyrium minitans CON/M/91-8）+SX、クリプトコッカス・アルビダス（cryptococcus albidus）+SX、エルビニア・カロトボーラsubsp.カロトボーラCGE234M403株（Erwinia carotovora subsp.carotovora CGE234M403）+SX、フザリウム・オキシスポラムFo47株（Fusarium oxysporum Fo47）+SX、グリオクラディウム・カテヌラタムJ1446株（Gliocladium catenulatum J1446）+SX、パエニバチルス・ポリミキサAC-1株（Paenibacillus polymyxa AC-1）+SX、パエニバチルス・ポリミキサBS-0105株（Paenibacillus polymyxa BS-0105）+SX、パントエア・アグロメランスE325株（Pantoea agglomerans E325）+SX、フレビオプシス・ギガンテアVRA1992株（Phlebiopsis gigantea VRA1992）+SX、シュードモナス・オーレオファシエンスTX-1株（Pseudomonas aureofaciens TX-1）+SX、シュードモナス・クロロラフィス63-28株（Pseudomonas chlororaphis 63-28）+SX、シュードモナス・クロロラフィス MA342株（Pseudomonas chlororaphis MA342）+SX、シュードモナス・フルオレッセンス1629RS株（Pseudomonas fluorescens 1629RS）+SX、シュードモナス・フルオレッセンスA506株（Pseudomonas fluorescens A506）+SX、シュードモナス・フルオレッセンス CL145A株（Pseudomonas fluorescens CL145A）+SX、シュードモナス・フルオレッセンス G7090株（Pseudomonas fluorescens G7090）+SX、シュードモナスsp.CAB-02株（Pseudomonas sp. CAB-02）+SX、シュードモナス・シリンガエ742RS株（Pseudomonas syringae 742RS）+SX、シュードモナス・シリンガエMA-4株（Pseudomonas syringae MA-4）+SX、シュードザイマ・フロキュローサPF-A22UL株（Pseudozyma flocculosa PF-A22UL）+SX、シュードモナス・ロデシアHAI-0804株（Pseudomonas rhodesiae HAI-0804）+SX、ピシウム・オリガンドラムDV74株 （Pythium oligandrum DV74）+SX、ストレプトマイセス・グリセオビリジスK61株 （Streptomyces griseoviridis K61）+SX、ストレプトマイセス・リジカスWYCD108US株（Streptomyces lydicus WYCD108US）+SX、ストレプトマイセス・リジカスWYEC108株（Streptomyces lydicus WYEC108）+SX、タラロマイセス・フラバスSAY-Y-94-01株（Talaromyces flavus SAY-Y-94-01）+SX、タラロマイセス・フラバスV117b株（Talaromyces flavus V117b）+SX、トリコデルマ・アスペレルムICC012株（Trichoderma asperellum ICC012）+SX、トリコデルマ・アスペレルムSKT-1株（Trichoderma asperellum SKT-1)+SX、トリコデルマ・アスペレルムT34株 （Trichoderma asperellum T34）+SX、トリコデルマ・アトロビリデ CNCM 1-1237株（Trichoderma atroviride CNCM 1-1237）+SX、トリコデルマ・アトロビリデLC52株（Trichoderma atroviride LC52）+SX、トリコデルマ・アトロビリデSC1株（Trichoderma atroviride SC1）+SX、トリコデルマ・アトロビリデ SKT-1株（Trichoderma atroviride SKT-1）+SX、トリコデルマ・ガムシーICC080株（Trichoderma gamsii ICC080）+SX、トリコデルマ・ハルジアナム21株（Trichoderma harzianum 21）+SX、トリコデルマ・ハルジアナム DB104株（Trichoderma harzianum DB104）+SX、トリコデルマ・ハルジアナム DSM 14944株（Trichoderma harzianum DSM 14944）+SX、トリコデルマ・ハルジアナム ESALQ-1303株（Trichoderma harzianum ESALQ-1303）+SX、トリコデルマ・ハルジアナム ESALQ-1306株（Trichoderma harzianum ESALQ-1306）+SX、トリコデルマ・ハルジアナム IIHR-Th-2株（Trichoderma harzianum IIHR-Th-2）+SX、トリコデルマ・ハルジアナムkd株（Trichoderma harzianum kd）+SX、トリコデルマ・ハルジアナム MO1株（Trichoderma harzianum MO1）+SX、トリコデルマ・ハルジアナムSF株（Trichoderma harzianum SF）+SX、トリコデルマ・ハルジアナム T22株（Trichoderma harzianum T22）+SX、トリコデルマ・ハルジアナム T39株（Trichoderma harzianum T39）+SX、トリコデルマ・ハルジアナムTEM908株（Trichoderma harzianum TEM908）+SX、トリコデルマ・ハルジアナムTH35株（Trichoderma harzianum TH35）+SX、トリコデルマ・ポリスポラムIMI 206039株（Trichoderma polysporum IMI 206039）+SX、トリコデルマ・ストロマチカム（trichoderma stromaticum）+SX、トリコデルマ・ビレンスG-41株（Trichoderma virens G-41)+SX、バリオボラックス・パラドクスCGF4526株（Variovorax paradoxus CGF4526）+SX、ハーピンタンパク（Harpin protein）+SX。 A combination of the present component of the above group (b) with the compound of the present invention:
Acibenzolar S methyl (acibenzolar-S-methyl) + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, amisulblom + SX, anilazine + SX, Azaconazole + SX, azoxystrobin + SX, basic copper sulfate + SX, benalaxyl + SX, benalaxyl M (benalaxyl-M) + SX, benodanil + SX, benomyl + SX, benchiavalicarab (benthiavalica b) + SX, bench avalia carib isopropyl (benthivalicarb-isopropyl) + SX, benzobin diflupyr (benzovidiflupyr) + SX, binapacryl (Spa, bax) Biphenyl (biphenyl) + SX, bitertanol (bitertanol) + SX, bixafen (bixafen) + SX, blastsaidin S (blasticidin-S) + SX, Bordeaux solution (Bordeaux mixture) + SX, boscalid + SX, bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, captan + SX, carvender Jim (carbendazim) + SX, carboxin + SX, carpropamide (carpropamid) + SX, quinomethionate + SX, chitin (chitin) + SX, chloroneb (chloroneb) + SX, chlorothalonil + SX, Clozolinate (chlozolinate) + SX, colletochlorin B (B) + SX, copper (II) acetate (copper (II) acetate) + SX, copper (II) hydroxide (copper (II) hydroxide) + SX, basic chloride Copper (copper oxychloride) + SX, copper (II) (copper (II) sulfate) + SX, coxoxystrobin + SX, cyazofamid (cyazofamid) + SX, cyflufenamide (cyflufenamid) + SX, shimoxanyl (cymoxanil ) + SX, Proconazole (cyproconazole) + SX, cyprodinil + SX, dichlobentiazox + SX, dichlofluanid (dichlofluanid) + SX, diclocymet (diclocymet) + SX, diclomezine (diclomezine) + SX, dichloran (diclomezine) dicloran) + SX, diethofencarb + SX, difenoconazole + SX, diflumetorim + SX, dimethaclone + SX, dimethirimol + SX, dimethomorph + diX Robin (dimoxystrobin) + SX, diniconazole (Diniconazole) + SX, diniconazole M (diniconazole-M) + SX, dino cup (dinocap) + SX, dipimethytron (dipymetitrone) + SX, dithianone (dithianon) + SX, bis dodecyl benzene sulfonate Ethylenediamine copper (II) complex salt (dodecylbenzenesulfonic acid bisethylenediamine copper (I I) salt) + SX, dodemorph + dox, dodine + Sx, edifenphos + sx, enoxastrobin + enx, epoxiconazole + sx, etaconazole + SX, ethaboxam + SX, ethirimol (ethirimol) + SX, etridiazole + SX, tea tree extract (extract from Melaleuca alternifolia) + SX, extract from Reynoutria sachalinensis + SX, Haute pomegranate Extract from cotyledon of sapling (extract from the cotyledons of lupine plantlets ("BLAD")) + SX, garlic extract (extract of Allium sativum) + SX, extractive extract (Equisetum arvense) + SX, orange extract Ingredients (extract of Tropaeolum majus) + SX, famoxadone + SX, fenamidone + SX, fenaminstrobin + SX, fe Narimol (fenarimol) + SX, fenbuconazole (fenbuconazole) + SX, fenfuram (fenfuram) + SX, fenhexamid (fenhexamid) + SX, fenoxanyl (fenoxanil) + SX, fenpiclonil (fenpiclonil) + SX, fenpicoxamide (Fenpicoxid) + SX, fenpropidin + SX, fenpropimorph + SX, fenpyrazamine + SX, triphenyltin acetate (fentin acetate) + SX, triphenyltin chloride (fentin chloride) + SX, triphenyltin hydroxide (fentin hydroxide) + SX, felbam + SX, ferimzone (Ferimzone) + SX, florylpicoxamide + SX, fluazinam + SX, fludioxonil (fludioxinil ) + SX, flufenoxystrobin + SX, fluindapyr + SX, flumorph + SX, fluopicolide (Fluopicolide) + SX, fluopimomide + SX, fluoroimide + SX, fluoxastrobin + SX, fluquinconazole (fluquinconazole) + SX, flusilazole (flusilazole) + SX, flusulfamide (flusulfamide) + SX, flutianil + SX, flutolanil + SX, flutriafol + SX, fluxapyroxad + SX, holpet (folpet) + SX, fosetyl + SX, Josel aluminum (fosetyl-aluminium) + SX, fuberidazole (fuberidazole) + SX, furalaxyl (Furalaxyl) + SX, furamethoyl (Furametpyr) + SX, gazatine (guazatine) + SX, hexaconazole (hexaconazole) + SX, hymexazole (hymexazole) ) + SX, Imazalil (imazalil) + SX, Imibenconazole (imibenconazole) + SX, Iminoctadine (iminoctadine) + SX, Minoctadine triacetate (iminoctadine triacetate) + SX, iodocarb (iodocarb) + SX, ipconazole (ipconazole) + SX, ipfentrifluconazole (ipfentrifluconazole) + SX, ipflufenoquin (ipflufenoquin) + SX, iprobenfos (iprobenfos) + SX, iprodione + SX, iprovalicarb + SX, isofetamide + SX, isoflucypram + SX, isoprothiolane + SX, isopyrazam + SX, isotianil (isotianil) + SX, kasugamycin + SX, kresoxim-methyl + SX, laminarin + SX, leaves and bark of Quercus + SX, mancozeb + SX, mandesto Robin (mandestrobin) + SX, mandipropamid (mandipropamid) + SX, manneb (maneb) + SX, mefentri Luconazole (mefentrifluconazole) + SX, mepanipyrim (Span), mepronil (mepronil) + SX, meptyldinocap + SX, metalaxyl (metalaxyl) + SX, metalaxyl M (metalaxyl-M) + SX, metconazole metconazole) + SX, metasulfocarb (methasulfocarb) + SX, methiram (metiram) + SX, metominostrobin + SX, metrafenone + SX, machine oil (mineral oils) + SX, microbutanil (myclobutanil) + SX, naftifine + SX, neem oil (neem oil) + SX, nuarimol (nuarimol) + SX, octilinone + SX, ofurace + SX, orysastrobin + SX, oxadixyl ) + SX, oxathiapiproline (oxathiapiprolin) + SX, oxine-copper + SX, oxolinic acid + SX, oxpoconazole (oxpoconazole) ) + SX, oxpoconazole fumarate + SX, oxycarboxin + SX, oxytetracycline + SX, pefrazoate + SX, penconazole + SX, penciclone (Pencycuron) + SX, penflufen + SX, penthiopyrad + SX, phenamacril + SX, phosphorous acid + SX, phthalide + SX, picalbutrazox (picarbutrazox (picarbutrazox) ) + SX, picoxystrobin + SX, piperalin (piperalin) + SX, polyoxins (polyoxins) + SX, potassium hydrogencarbonate (potassium hydrogencarbonate) + SX, potassium diphosphite (potassium dihydrogenphosphate) + SX Probenazole + SX, prochloraz + SX, procymidone + SX, propamidine (propamidi ne) + SX, propamocarb + SX, propiconazole + SX, propineb + SX, proquinazid + SX, prothiocarb + SX, prothioconazole (prothioconazole) + SX , Pydiflumetofen + SX, pyraclostrobin + SX, pyrametostrobin + SX, pyraoxystrobin + SX, pyrapropoyne + SX, pyradiflumid + SX, pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriofenone ) + SX, Pyrisoxazole + SX, Pyroquilon + SX, Quiraceae plant extract (Quill) aja extract + SX, quinconazole + SX, quinofumelin + SX, quinoxyfen + SX, quintozene + SX, Saponins of Chenopodia quinoa + SX, sedaxane (sedaxane) ) + SX, silthiofam + SX, simeconazole (simeconazole) + SX, sodium hydrogencarbonate + SX, spiroxamine + SX, streptomycin + SX, sulfur (sulfur) + SX, tebuconazole (Tebuconazole) + SX, tebufloquin + SX, teclofthalam + SX, tecnazene + SX, terbinafine + SX, tetraconazole (Straconazole) + SX, thiabendazole + SX, Thifluzamide + SX, thiophanate + SX, thiophanate methyl (thiophanate-me thyl) + SX, thiuram (thiram) + SX, thymol (thymol) + SX, tiadinil (tiadinil) + SX, tolclofos methyl (tolclofos-methyl) + SX, tolfenpyrad (tolfenpyrad) + SX, tolprocarb (tolprocarb) + SX, Tolylfluanid + SX, Triadimefon + SX, Triadimenol + SX, Triazoxide + SX, Triclopyricarb + SX, Tricyclazole + SX, Tridemorph tridemorph + SX, trifloxystrobin + SX, triflumizole + SX, triforine + SX, triticonazole + triticonazole + SX, validamycin + SX, varifenalate (Valifenalate) + SX, vinclozolin + SX, mustard powder (yellow mustard powder) + SX, zinc thiazole + SX, zineb (zine b) + SX, ziram + SX, zoxamide + SX, 3- (difluoromethyl) -N-methoxy-1-methyl-N-[(1R) -1-methyl-2- (2, 4,6-Trichlorophenyl) ethyl] pyrazole-4-carboxamide (1639015-48-7) + SX, 3- (Difluoromethyl) -N-methoxy-1-methyl-N-[(1S) -1-methyl- 2- (2,4,6-Trichlorophenyl) ethyl] pyrazole-4-carboxamide (1639015-49-8) + SX, 3- (difluoromethyl) -1-methyl-N- (1,1,3-trimethyl) Indan-4-yl) pyrazole-4-carboxamide (141573-94-6) + SX, 3- (difluoromethyl) -1-methyl-N-[(3R) -1,1,3-trimethylindan-4- [Illyl] pyrazole-4-carboxamide (1352994-67-2) + SX, 3 -(Difluoromethyl) -N-[(3R) -7-fluoro-1,1,3-trimethylindan-4-yl] -1-methylpyrazole-4-carboxamide (1513466-73-3) + SX, 3 -Chloro-5-phenyl-6
-Methyl-4- (2,6-difluorophenyl) pyridazine (1358061-55-8) + SX, N '-[4-({3-[(4-chlorophenyl) methyl] -1,2,4-thiadiazole -5-yl} oxy) -2,5-dimethylphenyl] -N-ethyl-N-methylmethaneimidamide (1202781-91-6) + SX, 2- {3- [2- (1-{[3] , 5-Bis (difluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -1,3-thiazol-4-yl] -4,5-dihydro-1,2-oxazole-5 -Yl} -3-chlorophenyl = methanesulfonate (1360819-11-9) + SX, 4- (2-bromo-4-fluorophenyl) -N- (2-chloro-6-fluorophenyl) -1,3 -Dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2, 2-di Methyl-9-fluoro-5- (quinolin-3-yl) -2,3-dihydrobenzo [f] [1,4] oxazepine (1207749-50-5) + SX, 2- [6- (3-fluoro) -4-Methoxyphenyl) -5-methylpyridin-2-yl] quinazoline (1257056-97-5) + SX, 5-fluoro-2-[(4-methylphenyl) methoxy] -4-pyrimidinamine (1174376- 25-0) + SX, 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2 (1H) -one (1616664-98-2) + SX, N'- ( 2,5-Dimethyl-4-phenoxyphenyl) -N-ethyl-N-methylmethaneimidamide (1052688-31-1) + SX, N '-{4-[(4,5-dichlorothiazol-2-yl] ) Oxy] -2,5-dimethylphenyl} -N-ethyl-N-methylmethaneimidamide (929908-57- 6) + SX, ethyl (2Z) -3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl) methyl] -N -Ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 1- [2-({[1- (4-chlorophenyl) -1H-pyrazol-3-yl] oxy } Methyl) -3-Methylphenyl] -4-methyl-5-oxo-4,5-dihydro-1H-tetrazole (1472649-01-6) + SX, α- [3- (4-chloro-2-fluoro) Phenyl) -5- (2,4-difluorophenyl) -4-isoxazolyl] -3-pyridinemethanol (1229605-96-2) + SX, (αS)-[3- (4-chloro-2-fluorophenyl) -5- (2,4-Difluorophenyl) -4-isoxazolyl] -3-pyridine methano (1229606-46-5) + SX, (αR)-[3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -4-isoxazolyl] -3-pyridinemethanol ( 1229606-02-3) + SX, 2-{[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1, 2,4-triazole-3-thione (1342260-19-8) + SX, 2-{[(2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane-2 -Yl] methyl} -2,4-dihydro-3H-1,2,4-triazole-3-thione (1638897-70-7) + SX, 2-{[(2S, 3R) -3- (2-) Chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4- Dihydro-3H-1,2,4-triazole-3-thione (1638897-71-8) + SX, 2-{[(2R, 3R) -3- (2-chlorophenyl) -2- (2,4-) Difluorophenyl) oxirane-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazole-3-thione (1638897-72-9) + SX, 2-{[(2S, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazole-3-thione (1638897- 73-0) + SX, 1-{[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazole-5- Ilthiocyanato (1342260-26-7) + SX, 1-{[(2R, 3S) -3- (2-chloro) Phenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl thiocyanate (1638897-82-1) + SX, 1-{[ (2S, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane-2-yl] methyl} -1H-1,2,4-triazol-5-yl thiocyanate (1638897- 84-3) + SX, 1-{[(2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2, 4-triazol-5-yl thiocyanato (1638897-86-5) + SX, 1-{[(2S, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxirane-2-] [I] methyl} -1H-1, 2, 4- triazo -5-yl thiocyanato (1638897-89-8) + SX, 5- (4-chlorobenzyl) -2-chloromethyl-2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) Cyclopentanol (1394057-11-4) + SX, (1R, 2S, 5S) -5- (4-chlorobenzyl) -2-chloromethyl-2-methyl-1- (1H-1,2,4-) Triazol-1-ylmethyl) cyclopentanol (1801930-06-2) + SX, (1S, 2R, 5R) -5- (4-chlorobenzyl) -2-chloromethyl-2-methyl-1- (1H- 1,2,4-Triazol-1-ylmethyl) cyclopentanol (1801930-07-3) + SX, (1R, 2R, 5R) -5- (4-chlorobenzyl) -2-chloromethyl-2-methyl -1- (1H-1,2,4-triazol-1-ylmethyl) cyclopente Nord (1801919-53-8) + SX, (1S, 2S, 5S) -5- (4-chlorobenzyl) -2-chloromethyl-2-methyl-1- (1H-1,2,4-triazole) 1-ylmethyl) cyclopentanol (1801919-54-9) + SX, (1R, 2R, 5S) -5- (4-chlorobenzyl) -2-chloromethyl-2-methyl-1- (1H-1 ,, 2,4-Triazol-1-ylmethyl) cyclopentanol (1801919-55-0) + SX, (1S, 2S, 5R) -5- (4-chlorobenzyl) -2-chloromethyl-2-methyl-1 -(1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (1801919-56-1) + SX, (1R, 2S, 5R) -5- (4-chlorobenzyl) -2-chloromethyl -2-Methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cycline Pentanol (1801919-57-2) + SX, (1S, 2R, 5S) -5- (4-chlorobenzyl) -2-chloromethyl-2-methyl-1- (1H-1,2,4-triazole) -1-ylmethyl) cyclopentanol (1801919-58-3) + SX, methyl 3-[(4-chlorophenyl) methyl] -2-hydroxy-1-methyl-2- (1H-1,2,4-) Triazol-1-ylmethyl) cyclopentanecarboxylate (1791398-02-1) + SX, methyl = (1R, 2S, 3S) -3-[(4-chlorophenyl) methyl] -2-hydroxy-1-methyl-2 -(1H-1,2,4-triazol-1-ylmethyl) cyclopentane carboxylate + SX, methyl = (1S, 2R, 3R) -3-[(4-chlorophenyl) methyl] -2-hydroxy-1- Methyl-2- (1H-1, 2,4-Triazol-1-ylmethyl) cyclopentane carboxylate + SX, methyl = (1R, 2R, 3R) -3-[(4-chlorophenyl) methyl] -2-hydroxy-1-methyl-2- (1H -1,2,4-Triazol-1-ylmethyl) cyclopentane carboxylate + SX, methyl = (1S, 2S, 3S) -3-[(4-chlorophenyl) methyl] -2-hydroxy-1-methyl-2 -(1H-1,2,4-triazol-1-ylmethyl) cyclopentane carboxylate + SX, methyl = (1R, 2R, 3S) -3-[(4-chlorophenyl) methyl] -2-hydroxy-1- Methyl-2- (1H-1,2,4-triazol-1-ylmethyl) cyclopentane carboxylate + SX, methyl = (1S, 2S, 3R) -3-[(4-) Rolophenyl) methyl] -2-hydroxy-1-methyl-2- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanecarboxylate + SX, methyl = (1R, 2S, 3R) -3- [ (4-Chlorophenyl) methyl] -2-hydroxy-1-methyl-2- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanecarboxylate + SX, methyl = (1S, 2R, 3S)- 3-[(4-Chlorophenyl) methyl] -2-hydroxy-1-methyl-2- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanecarboxylate + SX, 2-chloromethyl-5- (4-Fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (1394057-13-6) + SX, (1R, (1R, S, 5S) -2-Chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (1801930-08-4) + SX, (1S, 2R, 5R) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol 1801930-09-5) + SX, (1R, 2R, 5R) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazole-1-l) (Ilmethyl) cyclopentanol (1638898-08-4) + SX, (1S, 2S, 5S) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,5 4-Triazol-1-ylmethyl) cyclopentanol (1638898-10-8) + SX, (1R, 2R, 5S) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol 1638898-13-1) + SX, (1S, 2S, 5R) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,4-triazole-1) (Ilmethyl) cyclopentanol (1638898-16-4) + SX, (1R, 2S, 5R) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- (1H-1,2,6 4-Triazol-1-ylmethyl) cyclopentanol (1638898-20-0) + SX, (1S, 2R, 5S) -2-chloromethyl-5- (4-fluorobenzyl) -2-methyl-1- ( 1H-1,2,4-triazol-1-ylmethyl) cyclopentano (1638898-24-4) + SX, (R) -2- [2-chloro-4- (4-chlorophenoxy) phenyl] -1- (1,2,4-triazol-1-yl) pent-3 -In-2-ol (1801919-59-4) + SX, (R) -2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1,2,4 -Triazol-1-yl) propan-2-ol (1616236-94-2) + SX, (R) -1- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- Cyclopropyl-2- (1,2,4-triazol-1-yl) ethanol (1801919-60-7) + SX, (R) -2- [4- (4-chlorophenoxy) -2- (trifluoro) (Methyl) phenyl] -3-methyl-1- (1,2,4-triazol-1-yl) butan-2-ol (1801919-61-8) + S X, 3- [5- (4-chlorophenyl) -2,3-dimethyl-1,2-oxazolidin-3-yl] pyridine (847749-37-5) + SX,
Agrobacterium radiobacter K1026 (Agrobacterium radiobactor K1026) + SX, Agrobacterium radiobacter K 84 (Agrobacterium radiobactor K84) + SX, Bacillus amyloliquefaciens AT 332 (Bacillus amyloliquefaciens AT 332) + SX, Bacillus. Amyloliquefaciens B3 strain (Bacillus amyloliquefaciens B3) + SX, Bacillus amyloliquefaciens strain D747 (Bacillus amyloliquefaciens D747) + SX, Bacillus amyloliquefaciens strain DB101 (bacillus amyloliquefaciens DB101) + SX, Bacillus amyloliquefaciens DB101 Faciens DB102 strain (Bacillus amyloliquefaciens DB102) + SX, Bacillus amyloliquefaciens GB03 strain (Bacillus amyloliquefaciens GB03) + SX, Bacillus amyloliquefaciens FZB24 strain (Bacillus amyloliquefaciens FZB24) + SX, Bacillus amyloliquefaciens FZB42 strain (Bacillus amyloliquefaciens FZB42) + SX, batil Amyloliquefaciens strain IN 937a (Bacillus amyloliquefaciens IN937a) + SX, Bacillus amyloliquefaciens MBI 600 strain (Bacillus amyloliquefaciens MBI 600) + SX, Bacillus amyloliquefaciens strain QST 713 (Bacillus amyloliquefaciens QST 713) + SX, Bacillus amyloliquefaciens QST 713 Liquefaciens isolate B246 (Bacillus amyloliquefaciens isolate B246) + SX, Bacillus amyloliquefaciens F727 (bacillus amyloliquefaciens F727) + SX, Bacillus licheniformis HB-2 (Bacillus licheniformis HB-2) + SX, Bacillus · Licheniformis SB3086 strain (Bacillus licheniformis SB3086) + SX, Bacillus pumilus AQ 717 strain (Bacillus pumilus AQ 717) + SX, Bacillus pumilus BUF-33 strain (Bacillus pumilus BUF-33) + SX, Bacillus pumilus GB 34 strain (Bacillus pumilus) GB 34) + SX, Bacillus pumilus QST 2808 (Bacillus pumilus QST 2808) + SX, Bacillus simplex CGF 2 856 (Bacillus simplex CGF 2856) + SX, Bacillus subtilis AQ 153 strain (Bacillus subtilis AQ 153) + SX, Bacillus subtilis A Q 743 strain (Bacillus subtilis AQ 743) + SX, Bacillus subtilis BU 1814 strain (Bacillus subtilis BU 1814) + SX, Bacillus subtilis D747 strain (Bacillus subtilis D747) + SX, Bacillus subtilis DB 101 strain (Bacillus subtilis DB 101) + SX, Bacillus subtilis FZB 24 strain (Bacillus subtilis FZB24) + SX, Bacillus subtilis GB 03 strain (Bacillus subtilis GB 03) + SX, Bacillus · S. subtilis HAI 0404 strain (Bacillus subtilis HAI 0404) + SX, Bacillus subtilis IAB / BS03 strain (Bacillus subtilis IAB / BS03) + SX, Bacillus subtilis MBI 600 strain (Bacillus subtilis MBI 600) + SX, Bacillus subtilis QST 30002 / AQ 30002 ( Bacillus subtilis QST30002 / AQ30002) + SX, Bacillus subtilis QST30004 / AQ30004 (Bacillus subtilis QST30004 / AQ30004) + SX, Bacillus subtilis Sus QST 713 (Bacillus subtilis QST 713) + SX, Bacillus subtilis QST 714 (Bacillus subtilis QST 714) + SX, Bacillus subtilis var. Strain (Bacillus subtilis Y1336) + SX, Burkholderia cepacia + SX, Burkholderia cepacia-Wisconsin type J 82 (Burkholderia cepacia type Wisconsin J 82) + SX, Burkholderia cepacia · Wisconsin type M 54 Strain (Burkholderia cepacia type Wisconsin M54) + SX, Candida oleophila O strain (Candida oleophila O) + SX, Candida saitoana (Candida saitoana) + SX, ketomium cupreum (Chaetomium cupreum) + SX, chronostasis rosea ( Clonostachys rosea) + SX, Coniothyrium minitans CGMCC 83 25 (Coniothyrium minitans CGMCC 83 25) + SX Coniosium minitans CON / M / 91-8 (Coniothyrium minitans CON / M / 91-8) + SX, Cryptococcus albidus (cryptococcus albidus) + SX, Erwinia carotobola subsp. ) + SX, Fusarium oxysporum Fo 47 strain (Fusarium oxysporum Fo 47) + SX, Gliocladium catenulatum J 1446 strain (Gliocladium catenulatum J 1446) + SX, Paenibacillus polymyxa AC-1 strain (Paenibacillus polymyxa AC-1) + SX, Paenibacillus polymyxa BS-0105 strain (Paenibacillus polymyxa BS-0105) + SX, Pantoea agglomerans E 325 strain (Pantoea agglomerans E 325) + SX, Flebiopsis gigantea VRA 1992 strain (Phlebiopsis gigantea VRA 1992) + SX, Pseudomonas aleophysicus TX -1 strain (Pseudomonas aureofaciens TX-1) + SX, Pseudomonas chlorolafis 63-28 strain (Pseudomonas chl ororaphis 63-28) + SX, Pseudomonas chlorolaphis MA 342 strain (Pseudomonas chlororaphis MA 342) + SX, Pseudomonas fluorescens 1629 RS strain (Pseudomonas fluorescens 1629 RS) + SX, Pseudomonas fluorescens A 506 strain (Pseudomonas fluorescens A506) + SX Pseudomonas fluorescens CL145A (Pseudomonas fluorescens CL145A) + SX, Pseudomonas fluorescens G7090 (Pseudomonas fluorescens G7090) + SX, Pseudomonas sp. CAB-02 strain (Pseudomonas sp. Strain (Pseudomonas syringae 742 RS) + SX, Pseudomonas syringae MA-4 strain (Pseudomonas syringae MA-4) + SX, Pseudozyma flocculosa PF-A22UL strain (Pseudozyma flocculosa PF-A22UL) + SX, Pseudomonas rhodesia HAI-804 strain (Pseudomonas rhodesiae HAI-0804) + SX, Pythium oligand Rum DV 74 strain (Pythium oligodrum DV 74) + SX, Streptomyces griseoviridis K 61 strain (Streptomyces griseoviridis K 61) + SX, Streptomyces lydicus WYCD 108 US strain (Streptomyces lydicus WYCD 108 US) + SX, Streptomyces lyzicus WYEC 108 strain (Streptomyces lydicus WYEC 108) Talaromyces flavus SAY-Y-94-01 (Talaromyces flavus SAY-Y-94-01) + SX, Talaromyces flavus V117b (Talaromyces flavus V117b) + SX, Trichoderma asperum ICC 012 (Trichoderma asperellum ICC 012) + SX , Trichoderma asperomem SKT-1 (Trichoderma asperellum SKT-1) + SX, Trichoderma asperomeum T34 (Trichoderma asperellum T34) + SX, Trichoderma atroviride CNCM 1-1237 (Trichoderma atroviride CNCM 1-1237) + SX, Trichoderma atroviride LC 52 (Trichoderma atroviride LC 52) + SX, Trichoderma atroviride SC 1 (Trichoderma atroviride SC 1) + SX Trichoderma atroviride strain SKT-1 (Trichoderma atroviride SKT-1) + SX, Trichoderma gumsi ICC 080 strain (Trichoderma gamsii ICC 080) + SX, Trichoderma harzianum 21 strain (Trichoderma harzianum 21) + SX, Trichoderma harzianum DB 104 harzianum DB104) + SX, Trichoderma harzianum DSM 14944 strain (Trichoderma harzianum DSM 14944) + SX, Trichoderma harzianum ESALQ-1303 strain (Trichoderma harzianum ESALQ-1303) + SX, Trichoderma harzianum ESALQ-1306 strain (Trichodermahar) 1306) + SX, Trichoderma harzianum IIHR-Th-2 strain (Trichoderma harzianum IIHR-Th-2) + SX, Trichoderma harzianum kd strain (Trichoderma harzianum kd) + SX, Trichoderma harzianum MO1 strain (Trichoderma harzianum MO1) + SX, Trichoderma harzianum SF strain (Trichoderma harzianum SF) + SX, Trichoderma harziana T22 strain (Trichoderma harzianum T22) + SX, Trichoderma harzianum T39 strain (Trichoderma harzianum T39) + SX, Trichoderma harzianum TEM 908 strain (Trichoderma harzianum TEM 908) + SX, Trichoderma harzianum TH35 strain (Trichoderma harzianum 35) Polysporum IMI 206039 (Trichoderma polysporum IMI 206039) + SX, Trichoderma stromaticum + SX, Trichoderma virens G-41 strain (Trichoderma virens G-41) + SX, Varioborac paradox CGF 4526 (Variovorax paradoxus CGF 4526) + SX, Harpin protein + SX.
上記群（ｃ）の本成分と本発明化合物との組み合わせ：
　１－メチルシクロプロペン（1-methylcyclopropene）+SX、2,3,5－トリヨード安息香酸（2,3,5-triiodobenzoic acid）+SX、IAA（(1H-インドール-3-イル)酢酸（(1H-indol-3-yl)acetic acid））+SX、IBA（4-(1H-インドール-3-イル)酪酸（（4-(1H-indol-3-yl)butyric acid））+SX、MCPA（2-（4-クロロ-2-メチルフェノキシ)酢酸（2-（4-chloro-2-methylphenoxy）acetic acid））+SX、MCPB（4-(4-クロロ-2-メチルフェノキシ)酢酸（4-(4-chloro-2-methylphenoxy)butyric acid））+SX、4-CPA（4-chlorophenoxyacetic acid）+SX、５－アミノレブリン酸塩酸塩（5-aminolevulinic acid hydrochloride）+SX、６－ベンジルアミノプリン（6-benzylaminopurine）+SX、アブシシン酸（abscisic acid）+SX、AVG（aminoethoxyvinylglycine）+SX、アンシミドール（ancymidol）+SX、ブトルアリン（butralin）+SX、炭酸カルシウム（calcium carbonate）+SX、塩化カルシウム（calcium chloride）+SX、ギ酸カルシウム（calcium formate）+SX、過酸化カルシウム（calcium peroxide）+SX、石灰硫黄（calcium polysulfide）+SX、硫酸カルシウム（calcium sulfate）+SX、クロルメコートクロリド（chlormequat-chloride）+SX、クロロプロファム（chlorpropham）+SX、塩化コリン（choline chloride）+SX、クロプロップ（cloprop）+SX、シアナミド（cyanamide）+SX、シクラニリド（cyclanilide）+SX、ダミノジッド（daminozide）+SX、デカン－１－オール（decan-1-ol）+SX、ジクロプロップ（dichlorprop）+SX、ジケグラック（dikegulac）+SX、ジメチピン（dimethipin）+SX、ジクワット（diquat）+SX、エテホン（ethephon）+SX、エチクロゼート（ethychlozate）+SX、フルメトラリン（flumetralin）+SX、フルルプリミドール（flurprimidol）+SX、ホルクロルフェヌロン（forchlorfenuron）+SX、ジベレリンＡ（Gibberellin A）+SX、ジベレリンＡ３（Gibberellin A3）+SX、イナベンフィド（inabenfide）+SX、カイネチン（Kinetin）+SX、マレイン酸ヒドラジド（maleic hydrazide）+SX、メフルイジド（mefluidide）+SX、メピコートクロリド（mepiquat-chloride）+SX、酸化型グルタチオン（oxidized glutathione）+SX、パクロブトラゾール（pacrobutrazol）+SX、ペンディメタリン（pendimethalin）+SX、プロヘキサジオンカルシウム（prohexandione-calcium）+SX、プロヒドロジャスモン（prohydrojasmon）+SX、ピラフルフェンエチル（pyraflufen-ethyl）+SX、シントフェン（sintofen）+SX、１－ナフタレン酢酸ナトリウム（sodium 1-naphthaleneacetate）+SX、シアン酸ナトリウム（sodium cyanate）+SX、ストレプトマイシン（streptmycin）+SX、チジアズロン（thidiazuron）+SX、トリアペンテノール（triapenthenol）+SX、トリブホス（Tribufos）+SX、トリネキサパックエチル（trinexapac-ethyl）+SX、ウニコナゾールP（uniconazole-P）+SX、２－（ナフタレン－１－イル）アセトアミド（2-(naphthalene-1-yl)acetamide）+SX、［４－オキソ－４－（２－フェニルエチル）アミノ］酪酸+SX、５－（トリフルオロメチル）ベンゾ［b］チオフェン－２－カルボン酸メチル+SX、３－［（６－クロロ－４－フェニルキナゾリン－２－イル）アミノ］－１－プロパノール+SX、ホルモノネチン（isoflavone formononetin）+SX、グロマス・イントララディセス（Glomus intraradices）+SX、グロマス・モッセ（Glomus mosseae）+SX、グロマス・アグリゲイツム（Glomus aggregatum）+SX、グロマス・エツニカツム（Glomus etunicatum）+SX、ブラディリゾビウム・エルカニ（Bradyrhizobium elkani）+SX、ブラディリゾビウム・ジャポニカム（Bradyrhizobium japonicum）+SX、ブラディリゾビウム・ルピニ（Bradyrhizobium lupini）+SX、リゾビウム・レグミノサルム bv. トリホリ（Rhizobium leguminosarum bv. trifolii）+SX、リゾビウム・レグミノサルム bv. ファゼオリ（Rhizobium leguminosarum bv. phaseoli）+SX、リゾビウム・レグミノサルム bv.ビシアエ（Rhizobium leguminosarum bv. viciae）+SX、シノリゾビウム・メリロチ（Sinorhizobium meliloti）+SX、リゾビウム・フレディ（Rhizobium fredii）+SX、リゾビウム・ロチ（Rhizobium loti）+SX、リゾビウム・トリホリ（Rhizobium trifolii）+SX、リゾビウム・トロピシ（Rhizobium tropici）+SX、１,３－ジフェニルウレア（1,3-diphenylurea） +SX、リポキトオリゴ糖SP104（lipochitooligosaccharide SP104） +SX、アゾリゾビウム・カウリノダンス（Azorhizobium caulinodans）+SX、アゾスピリルム・アマゾネンス（Azospirillum amazonense）+SX、アゾスピリルム・ブラシレンセ XOH（Azospirillum brasilense XOH）+SX、アゾスピリルム・ブラシレンセAb-V5（Azospirillum brasilense Ab-V5）+SX、アゾスピリルム・ブラシレンセAb-V6（Azospirillum brasilense Ab-V6）+SX、アゾスピリルム・カウリノダンス（Azospirillum caulinodans）+SX、アゾスピリルム・ハロプラエフェレンス（Azospirillum halopraeferens）+SX、アゾスピリルム・イケランス（Azospirillum irakense）+SX、アゾスピリルム・リポフェルム（Azospirillum lipoferum）+SX、ブラディリゾビウム・エルカニ SEMIA 587（Bradyrhizobium elkanii SEMIA 587）+SX、ブラディリゾビウム・エルカニ SEMIA 5019（Bradyrhizobium elkanii SEMIA 5019）+SX、ブラディリゾビウム・ジャポニカム TA-11（Bradyrhizobium japonicum TA-11）+SX、ブラディリゾビウム・ジャポニカム USDA 110（Bradyrhizobium japonicum USDA 110)+SX、ブラディリゾビウム・リアオニンゲンス（Bradyrhizobium liaoningense）+SX、クラロイデオグロムス・クラロイデウム（Claroideoglomus claroideum）+SX、デルフチア・アシドボランス RAY209（Delftia acidovorans RAY209）+SX、ギガスポラ・マルガリータ（Gigaspora margarita）+SX、ギガスポラ・ロセア（Gigaspora rosea）+SX、グルムス・デセルチコラ（Glomus deserticola）+SX、グルムス・モノスポルム（Glomus monosporum）+SX、メソリゾビウム・シセリ（Mesorhizobium ciceri）+SX、メソリゾビウム・フワクイ（Mesorhizobium huakii）+SX、リゾファガス・クラルス（Rhizophagus clarus）+SX、リゾビウム・エトリ（Rhizobium etli）+SX、リゾビウム・ガレガーエ（Rhizobium galegae）+SX、リゾファガス・イレグラリス DAOM 19719（Rhizophagus irregularis DAOM 197198)+SX、パラグロムス・ブラシリアヌム（Paraglomus brasillianum）+SX。 A combination of the present component of the above group (c) with the compound of the present invention:
1-methylcyclopropene (1-methylcyclopropene) + SX, 2,3,5-triiodobenzoic acid (2, 3,5- triiodobenzoic acid) + SX, IAA ((1H-indol-3-yl) acetic acid ((1H) -indol-3-yl) acetic acid)) + SX, IBA (4- (1H-indol-3-yl) butyric acid ((4- (1H-indol-3-yl) butyric acid)) + SX, MCPA ( 2- (4-chloro-2-methylphenoxy) acetic acid (2- (4-chloro-2-methylphenoxy) acetic acid) + SX, MCPB (4- (4-chloro-2-methylphenoxy) acetic acid (4- (4-chloro-2-methylphenoxy) acetic acid) (4-chloro-2-methylphenoxy) butyric acid)) + SX, 4-CPA (4-chlorophenoxyacetic acid) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine ( 6-benzylaminopurine) + SX, abscisic acid (Abscisic acid) + SX, AVG (aminoethoxyvinylglycine) + SX, ancsimidol (ancymidol) + SX, butralin (butralin) + SX, calcium carbonate + SX, calcium chloride (Calcium chloride) + SX, formic acid Calcium formate + SX, calcium peroxide (Silper peroxide) + SX, calcium sulfur (calcium polysulfide) + SX, calcium sulfate (calcium sulfate) + SX, chlormequat chloride (chlormequat-chloride) + SX, chloropro Fem (chlorpropham) + SX, choline chloride + SX, cloprop (SX), cyanamide (Cyanamide) + SX, cyclanilide (SX), daminozide + SX, decane-1-ol (Decan-1-ol) + SX, dichlorprop + SX, dikegulac + SX, dimethipin + SX, diquat + SX, ethephon + SX, ethychlozate + SX, flumetralin + SX, flurprimidol + SX, forchlorfenuron + SX, gibberellin A (Gibberellin A) + SX, gibberellin A3 (Gibberel lin A3) + SX, inabenfide (inabenfide) + SX, kinetin (Kinetin) + SX, maleic acid hydrazide (maleic hydrazide) + SX, mefluidide (mefluidide) + SX, mepiquat chloride (mepiquat-chloride) + SX, oxidation Type glutathione (oxidized glutathione) + SX, paclobutrazol (pacrobutrazol) + SX, pendimethalin (pendimethalin) + SX, prohexadione calcium (prohexandione-calcium) + SX, prohydrojasmon (prohydrojasmon) + SX, pilaf Ruphenethyl (pyraflufen-ethyl) + SX, sintofen + SX, 1-sodium naphthaleneacetate (sodium 1-naphthaleneacetate) + SX, sodium cyanate (sodium cyanate) + SX, streptomycin (streptomycin) + SX, thidiazuron (Thidiazuron) + SX, triapenthenol + SX, tribufos (Tribufos) + SX, trinexapac ethyl (trinexapac-ethyl) + SX Uniconazole P (uniconazole-P) + SX, 2- (Naphthalen-1-yl) acetamide (2- (naphthalene-1-yl) acetamide) + SX, [4-oxo-4- (2-phenylethyl) amino ] Butyric acid + SX, methyl 5- (trifluoromethyl) benzo [b] thiophene-2-carboxylate + SX, 3-[(6-chloro-4-phenylquinazolin-2-yl) amino] -1-propanol + SX, hormononetin (isoflavone formononetin) + SX, Glomas intraradices (Glomus intraradices) + SX, Glomas mosse (Glomus mosseae) + SX, Glomas aggregatum (Glomus aggregatum) + SX, Glomas etunisitum (Glomus etunicatum) SX, Bradyrhizobium elkani + SX, Brady rhizobium japonicum + SX, Brady rhizobium lupini (Bradyrhizobium lupini) + SX, Rhizobium leguminosarum bv. Trifolii + SX, Rhizobium legumino salum bv. Phazoe (Rhizobium leguminosarum bv. Phaseoli) + SX, Rhizobium legminosalm bv. Rhizobium Sinorhizobium meliloti + SX, Rhizobium fredii + SX, Rhizobium loti + SX, Rhizobium trifolii + SX, Rhizobium tropius + SX 1,3-Diphenylurea (1,3 diphenylurea) + SX, Lipochitooligosaccharide SP104 (lipothiotooligosaccharide SP 104) + SX, Azorhizobium caulinodans + SX XOH (Azospirillum brasilense XOH) + SX, Azo Spiritum braiensense Ab-V5 (Azospirillum brasilense Ab-V5) + SX, azospirilum braiensense Ab-V6 (Azospirillum brasilense Ab-V6) + SX, azospirilum caulinodans + SX, azospirilum ・ halopellaphiles ) + SX, Azospirillum irakense + SX, Azospirillum lipoferum (Azospirillum lipoferum) + SX, Brady Rhizobium elcani SEMIA 587 (Bradyrhizobium elkanii SEMIA 587) + SX, Brady Rhizobium Elkani Bradyrhizobium elkanii SEMIA 5019) + SX, Brady Rhizobium japonicum TA-11 (Bradyrhizobium japonicum TA-11) + SX, Brady Rhizobium japonicum USDA 110 (Bradyrhizobium japonicum USDA 110) + SX, Brady Rhizobium・ Liaoningens (Bradyrhizobium liooningense) + SX, Claroideogro S. Claroideum (Claroideoglomus claroideum) + SX, Delphithia Acidoboranes RAY 209 (Delftia acidovorans RAY 209) + SX, Gigaspora margarita (Gigaspora margarita) + SX, Gigaspora rosea (Sig) + SX, Glmus de Cellicolac SX, Glomus monosporum + SX, Mesorhizobium ciceri + SX, Mesorhizobium huakii + SX, Rhizophagus clarus + SX, Rhizobium + Rhizobium et al. SX, Rhizobium galegae + SX, Rhizophagus ieglalis DAOM 19719 (Rhizophagus irregularis DAOM 197198) + SX, Paraglomus brasillianum + SX.
上記群（ｄ）の本成分と本発明化合物との組み合わせ：
　アリドクロール（allidochlor）+SX、ベノキサコール（benoxacor）+SX、クロキントセット（cloquintocet）+SX、クロキントセットメキシル（cloquintocet-mexyl）+SX、シオメトリニル（cyometrinil）+SX、シプロスルファミド（cyprosulfamide）+SX、ジクロルミド（dichlormid）+SX、ジシクロノン（dicyclonone）+SX、ジメピペラート（dimepiperate）+SX、ジスルホトン（disulfoton）+SX、ダイムロン（dymron）+SX、フェンクロラゾール（fenchlorazole）+SX、フェンクロラゾールエチル（fenchlorazole-ethyl）+SX、フェンクロリム（fenclorim）+SX、フルラゾール（flurazole）+SX、フリラゾール（furilazole）+SX、フルキソフェニム（fluxofenim）+SX、ヘキシム（Hexim）+SX、イソキサジフェン（isoxadifen）+SX、イソキサジフェンエチル（isoxadifen-ethyl）+SX、メコプロップ（mecoprop）+SX、メフェンピル（mefenpyr）+SX、メフェンピルエチル（mefenpyr-ethyl）+SX、メフェンピルジエチル（mefenpyr-diethyl）+SX、メフェナート（mephenate）+SX、メトカミフェン（metcamifen）+SX、オキサベトリニル（oxabetrinil）+SX、１，８－ナフタル酸無水物（1,8-naphthalic anhydride）+SX、１，８－オクタメチレンジアミン（1,8-octamethylene diamine）+SX、AD-67（4-(ジクロロアセチル)-1-オキサ-4-アザスピロ[4.5］デカン（（4-(dichloroacetyl)-1-oxa-4-azaspiro [4.5] decane））+SX、CL-304415 （4-カルボキシ-3,4-ジヒドロ-2H-1-ベンゾピラン-4-酢酸(4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid)）+SX、CSB（1-ブロモ-4-[(クロロメチル)スルホニル]ベンゼン（1-bromo-4-[(chloromethyl)sulfonyl]benzene））+SX、DKA-24（2,2-ジクロロ-N-[2-オキソ-2-(２－プロペニルアミノ)エチル]-N-(2-プロペニル)アセトアミド（2,2-dichloro-N-[2-oxo-2-(2-propenylamino)ethyl]-N-(2-propenyl)acetamide））+SX、MG191（2-(ジクロロメチル)-2-メチル-1,3-ジオキソラン（2-(dichloromethyl)-2-methyl-1,3-dioxolane））+SX、MG-838（2-プロペニル-1-オキサ-4-アザスピロ[4.5]デカン-4-カルボジチオレート）（2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate））+SX、PPG-1292（2,2-ジクロロ-N-(1,3-ジオキサン-2-イルメチル)-N-(2-プロペニル)アセトアミド（2,2-dichloro-N-(1,3-dioxan-2-ylmethyl)-N-(2-propenyl)acetamide））+SX、R-28725（3-(ジクロロアセチル)-2,2-ジメチル-1,3-オキサゾリジン（（3-(dichloroacetyl)-2,2-dimethyl-1,3-oxazolidine））+SX、R-29148（3-(ジクロロアセチル)-2,2,5-トリメチル-1,3-オキサゾリジン（3-(dichloroacetyl)-2,2,5-trimethyl-1,3-oxazolidine））+SX、TI-35（1-（ジクロロアセチル)アゼパン（1-(dichloroacetyl)azepane））+SX。 Combinations of the present component of the above group (d) with the compound of the present invention:
Aridochlor (allidochlor) + SX, benoxacor (benoxacor) + SX, cloquintoset (cloquintocet) + SX, cloquintocet mexyl (cloquintocet-mexyl) + SX, ciometrinil (cyometrinil) + SX, cyprosulfamide (cyprosulfamide) + SX, dichlormid (Diclormid) + SX, dicyclonone (Dicyclonone) + SX, dimepiperate (dimepiperate) + SX, disulfoton (disulfoton) + SX, dimron (dymron) + SX, fenchlorazole (Sintra) + SX, fenchlorazole Ethyl (fenchlorazole-ethyl) + SX, fenclorim (fenclorim) + SX, flurazole (flurazole) + SX, furilazole (furilazole) + SX, fluxophenim (fluxofenim) + SX, hexim (Hexim) + SX, isoxadifen (isoxadifen) + SX , Isoxadiphen-ethyl (isoxadifen-ethyl) + SX, mecoprop (mecoprop) + SX, mefenpyr (mefenpyr) + SX, mef Empirethyl (mefenpyr-ethyl) + SX, Mefenpyr-diethyl (Sef), Mephenate (mephenate) + SX, Metocamifen + SX, Oxabetrinil + SX, 1, 8 Naphthalic anhydride (1,8-naphthalic anhydride) + SX, 1,8-octamethylenediamine) + SX, AD-67 (4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] Decane ((4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane)) + SX, CL-304415 (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (4 -carboxyl-3,4-dihydro-2H-1-benzopyran-4-acetic acid)) + SX, CSB (1-bromo-4-[(chloromethyl) sulfonyl] benzene (1-bromo-4-[(chloromethyl) ) sulfonyl] benzene)) SX, DKA-24 (2, 2-Dichloro-N- [2-oxo-2- (2-propenylamino) ethyl] -N- (2-propenyl) acetamide (2, 2- dichloro-N- [2-oxo-2- (2-propenylamino) ethyl] -N- (2-propenyl) acetami de)) + SX, MG 191 (2- (dichloromethyl) -2-methyl-1,3-dioxolane (2- (dichloromethyl) -2-methyl-1,3-dioxolane)) + SX, MG-838 (2 -Propenyl-1-oxa-4-azaspiro [4.5] decane-4-carbodiiolate) (2-propenyl 1-oxa-4-azaspiro [4.5] decane-4-carbodithioate)) + SX, PPG-1292 (2 , 2-Dichloro-N- (1,3-dioxane-2-ylmethyl) -N- (2-propenyl) acetamide (2,2-dichloro-N- (1,3-dioxan-2-ylmethyl) -N- (2-propenyl) acetamide)) + SX, R-28725 (3- (dichloroacetyl) -2,2-dimethyl-1,3-oxazolidine ((3- (dichloroacetyl) -2,2-dimethyl-1,3 -oxazolidine)) + SX, R-29148 (3- (dichloroacetyl) -2,2,5-trimethyl-1,3-oxazolidine (3- (dichloroacetyl) -2,2,5-trimethyl-1,3-) oxazolidine)) + SX, TI-35 (1- (dichloroacetyl) azepane (1- (dichloroacetyl) azepane)) + SX.
上記群（ｅ）の本成分と本発明化合物との組み合わせ：
　１－ドデシル-１Ｈ－イミダゾール（1-dodecyl-1H-imidazole）+SX、Ｎ－（２－エチルへキシル）－８，９，１０－トリノルボルン－５－エン－２，３－ジカルボキシイミド（N-(2-ethylhexyl)-8,9,10-trinorborn-5-ene-2,3-dicarboximide）+SX、ブカルポレート（bucarpolate）+SX、Ｎ,Ｎ－ジブチル－４－クロロベンゼンスルホンアミド（N,N-dibutyl-4-chlorobenzenesulfonamide）+SX、ジエトレート（dietholate）+SX、ジエチルマレエート（diethylmaleate）+SX、ピペロニルブトキシド（piperonyl butoxide）+SX、ピペロニルシクロネン（piperonyl cyclonene）+SX、ピプロタル（piprotal）+SX、プロピルイソム（propyl isome）+SX、サフロキサン（safroxan）+SX、セサメックス（sesamex）+SX、セサモリン（sesamolin）+SX、スルホキシド（sulfoxide）+SX、ベルブチン（Verbutin）+SX、DMC（1,1-ビス(4-クロロフェニル)エタノール（1,1-bis(4-chloro
phenyl)ethanol））+SX、FDMC（1,1-ビス(4-クロロフェニル)-2,2,2-トリフルオロエタノール（1,1-bis(4-chlorophenyl)-2,2,2-trifluoroethanol））+SX、ETN（1,2-エポキシ-1,2,3,4-テトラヒドロナフタレン（1,2-epoxy-1,2,3,4-tetrahydronaphthalene））+SX、ETP（（1,1,1-トリクロロ-2,3-エポキシプロパン）（（1,1,1-trichloro-2,3-expoxypropane））+SX、PSCP（フェニルサリゲニンサイクリックホスフェート（phenylsaligenin cyclic phosphate））+SX、TBPT（S,S,S-トリブチル ホスホロトリチオレート（S,S,S-tributyl phosphorotrithioate）) +SX、TPP（トリフェニルホスフェート（triphenyl phosphate））+SX。 Combinations of the present component of the above group (e) with the compound of the present invention:
1-dodecyl-1H-imidazole (1-dodecyl-1H-imidazole) + SX, N- (2-ethylhexyl) -8,9,10-trinolborn-5-ene-2,3-dicarboximide (N -(2-ethylhexyl) -8,9,10-trinorborn-5-ene-2,3-dicarboximide + SX, bucarpolate + SX, N, N-dibutyl-4-chlorobenzenesulfonamide (N, N -dibutyl-4-chlorobenzenesulfonate) + SX, dietholate + SX, diethylmaleate (diethylmaleate) + SX, piperonyl butoxide + SX, piperonyl cycloclone + SX, piprotal + SX, propyl isome + SX, safroxan + SX, sesamex + SX, sesamolin + SX, sulfoxide (sulfoxide) + SX, verbutin + SX, DMC (1,1 1-bis (4-chlorophenyl) ethanol (1,1- bis (4-chloro
(phenyl) ethanol) + SX, FDMC (1,1-bis (4-chlorophenyl) -2,2,2-trifluoroethanol (1,1-bis (4-chlorophenyl) -2,2,2-trifluoroethanol) ) + SX, ETN (1,2-epoxy-1,2,3,4-tetrahydronaphthalene (1,2-epoxy-1,2,3,4-tetrahydronaphthalene)) + SX, ETP ((1,1,6) 1-trichloro-2,3-epoxypropane) ((1,1,1-trichloro-2,3-expoxypropane)) + SX, PSCP (phenylsaligenin cyclic phosphate) + SX, TBPT ( S, S, S-tributyl phosphorotrithioate (S, S, S-tributyl phosphorothioate) + SX, TPP (triphenyl phosphate) + SX.
上記群（ｆ）の本成分と本発明化合物との組み合わせ：
　アントラキノン（anthraquinone）+SX、クロラロース（chloralose）+SX、アクレップ（acrep）+SX、ブトピロノキシル（butopyronoxyl）+SX、カンファー（camphor）+SX、ｄ－カンファー（d-camphor）+SX、カルボキシド（carboxide）+SX、フタル酸ジブチル（dibutyl phthalate）+SX、ディート（deet）+SX、ジメチルカーバート（dimethyl carbate）+SX、フタル酸ジメチル（dimethyl phthalate）+SX、こはく酸ジブチル（dibutyl succinate）+SX、アジピン酸ジブチル（dibutyl adipate）+SX、エトヘキサジオール（ethohexadiol）+SX、ヘキサミド（hexamide）+SX、イカリジン（icaridin）+SX、メトキン－ブチル（methoquin-butyl）+SX、メチルネオデカナミド（methylneodecanamide）+SX、２－（オクチルチオ）エタノール（2-(octylthio)ethanol）+SX、ブトキシポリプロピレングリコール（butoxypolypropylene glycol)+SX、オキサメート（oxamate）+SX、quwenzhi+SX、quyingding+SX、zengxiaon+SX、レベミド（rebemide）+SX、ナフテン酸銅（copper naphthenate）+SX、ナフテン酸亜鉛（zinc naphthenate）+SX。 Combinations of the present component of the above group (f) with the compound of the present invention:
Anthraquinone (anthraquinone) + SX, chloralose + SX, acrep (acrep) + SX, butopyronoxyl (butopyronoxyl) + SX, camphor (camphor) + SX, d-camphor (d-camphor) + SX, carboxide (carboxide) ) + SX, dibutyl phthalate + SX, deet + SX, dimethyl carbamate + SX, dimethyl phthalate + SX, dibutyl succinate + SX , Dibutyl adipate + SX, ethohexadiol + SX, hexamidide + SX, icaridin (icaridin) + SX, methoquin-butyl (methoquin-butyl) + SX, methyl neodecanamide (Methylneodecanamide) + SX, 2- (Octylthio) ethanol + SX, butoxypolypropylene glycol + SX, oxamate (oxamat) e) + SX, quwenzhi + SX, quyingding + SX, zengxiaon + SX, rebemide + SX, copper naphthenate + SX, zinc naphthenate + zinc SX.
上記群（ｇ）の本成分と本発明化合物との組み合わせ：
　ビス（トリブチルチン）オキシド（bis(tributyltin) oxide）+SX、アリシン（allicin）+SX、ブロモアセトアミド（bromoacetamide）+SX、クロエトカルブ（cloethocarb）+SX、硫酸銅（copper sulfate）+SX、フェンチン（fentin）+SX、リン酸鉄（III）（ferric phosphate）+SX、メタアルデヒド（metaldehyde）+SX、ニクロスアミド（niclosamide）+SX、ペンタクロロフェノール（pentachlorophenol）+SX、ナトリウムペンタクロロフェノキシド（sodium pentachlorophenoxide）+SX、タジムカルブ（tazimcarb）+SX、トラロピリル（tralopyril）+SX、トリフェンモルフ（trifenmorph）+SX。 Combinations of this component of the above group (g) with a compound of the present invention:
Bis (tributyltin) oxide (bis (tributyltin) oxide) + SX, allicin (allicin) + SX, bromoacetamide (bromoacetamide) + SX, cloetocarb (s) + SX, copper sulfate (copper sulfate) + SX, phentin (fentin) ) + SX, ferric phosphate (ferric phosphate) + SX, metadehyde (metaldehyde) + SX, niclosamide (Niclosamide) + SX, pentachlorophenol + SX, sodium pentachlorophenoxide (sodium) SX, tazimcarb + SX, tralopyril + SX, trifenmorph + SX.
　上記群（ｈ）の本成分と本発明化合物との組み合わせ：
　(E)-2-ヘキサナール（(E)-2-hexenal）+SX、(E)-2-オクタデセナール（(E)-2-octadecenal）+SX、(E)-4-トリデセン-1-イル アセテート（(E)-4-tridecen-1-yl acetate）+SX、(E)-5-デセン-1-イル アセテート（(E)-5-decen-1-yl acetate）+SX、(E)-5-デセン-1-オール（(E)-5-decen-1-ol）+SX、(E)-3,3-ジメチルシクロヘキシリデンアセトアルデヒド（(E)-3,3-dimethylcyclohexylideneacetaldehyde）+SX、(E)-7-ドデセン-1-イル アセテート（(E)-7-dodecen-1-yl acetate）+SX、(E)-8-ドデセン-1-イル アセテート（(E)-8-dodecen-1-yl acetate）+SX、(E)-9-ドデセン-1-イル アセテート（(E)-9-dodecen-1-yl acetate）+SX、(E)-10-ヘキサデセナール（(E)-10-hexadecenal）+SX、(E)-11-ヘキサデセン-1-イル アセテート（(E)-11-hexadecen-1-yl acetate）+SX、(E)-11-テトラデセン-1-イル アセテート（(E)-11-tetradecen-1-yl acetate）+SX、(E)-11-テトラデセン-1-オール（(E)-11-tetradecen-1-ol）+SX、(E)-4-トリデセン-1-イル アセテート（(E)-4-tridecen-1-yl acetate）+SX、(E)-6-メチルへプタ-2-エン-4-オール（ (E)-6-methylhept-2-en-4-ol）+SX、(Z)-2-(3,3-ジメチルシクロヘキシリデン）エタノール（(Z)-2-(3,3-dimethylcyclohexylidene)ethanol）+SX、(Z)-4-デセン-1-イル アセテート（(Z)-4-decen-1-yl acetate）+SX、(Z)-4-トリデセン-1-イル アセテート（(Z)-4-tridecen-1-yl acetate）+SX、(Z)-5-デセン-1-イル アセテート（(Z)-5-decen-1-yl acetate）+SX、(Z)-5-デセン-1-オール（(Z)-5-decen-1-ol）+SX、(Z)-7-テトラデセナール（(Z)-7-tetradecenal）+SX、(Z)-7-ドデセン-1-イル アセテート（(Z)-7-dodecen-1-yl acetate）+SX、(Z)-8-ドデセン-1-イル アセテート（(Z)-8-dodecen-1-yl acetate）+SX、(Z)-9-ドデセン-1-イル アセテート（ (Z)-9-dodecen-1-yl acetate）+SX、(Z)-8-ドデセン-1-オール（ (Z)-8-dodecen-1-ol）+SX、(Z)-9-ヘキサデセナール（(Z)-9-hexadecenal）+SX、(Z)-10-ヘキサデセン-1-イル アセテート（(Z)-10-hexadecen-1-yl acetate）+SX、(Z)-11-ヘキサデセン-1-オール（(Z)-11-hexadecen-1-ol）+SX、(Z)-11-ヘキサデセナール（(Z)-11-hexadecenal）+SX、(Z)-11-ヘキサデセン-1-イル アセテート（(Z)-11-hexadecen-1-yl acetate）+SX、(Z)-11-オクタデセナール（(Z)-11-octadecenal）+SX、(Z)-13-オクタデセナール（(Z)-13-octadecenal）+SX、(Z)-ヘキサデカ-13-エン-1-イル アセテート（(Z)-hexadec-13-en-11-yn-1-yl acetate）+SX、(Z)-13-オクタデセナール（(Z)-13-octadecenal）+SX、(Z)-イコサ-13-エン-10-オン（(Z)-icos-13-en-10-one）+SX、(Z)-7-テトラデセナール（(Z)-7-tetradecenal）+SX、(Z)-テトラデカ-9-エン-1-オール（(Z)-tetradec-9-en-1-ol）+SX、(Z)-9-テトラデセン-１-イル アセテート（(Z)-9-tetradecen-1-yl acetate）+SX、(Z)-11-テトラデセン-1-イル アセテート（(Z)-11-tetradecen-1-yl acetate）+SX、(Z)-13-イコセン-10-オン（(Z)-13-icosen-10-one）+SX、(Z,E)-7,11-ヘキサデカジエン-1-イル アセテート（(Z,E)-7,11-hexadecadien-1-yl acetate）+SX、(Z,E)-9,12-テトラデカジエン-1-イル アセテート（(Z,E)-9,12-tetradecadien-1-yl acetate）+SX、(E,Z)-4,10-テトラデカジエン-1-イルアセテート（(E,Z)-4,10-tetradecadien-1-yl acetate）+SX、(E,E)-8,10-ドデカジエン-1-オール（(E,E)-8,10-dodecadien-1-ol）+SX、(E,E)-10,12-ヘキサデカジエナール（(E,E)-10,12-hexadecadienal）+SX、(E,E)-9,11-テトラデカジエン-1-イル アセテート（(E,E)-9,11-tetradecadien-1-yl acetate）+SX、(E,Z)-2,13-オクタデカジエン-1-オール（(E,Z)-2,13-octadecadien-1-ol）+SX、(E,Z)-3,13-オクタデカジエン-1-オール（(E,Z)-3,13-octadecadien-1-ol）+SX、(E,Z)-2,13-オクタデカジエン-1-イル アセテート（(E,Z)-2,13-octadecadien-1-yl acetate）+SX、(E,Z)-3,13-オクタデカジエン-1-イル アセテート（(E,Z)-3,13-octadecadien-1-yl acetate）+SX、(E,Z)-7,9-ドデカジエン-1-イル アセテート（(E,Z)-7,9-dodecadien-1-yl acetate）+SX、(E,E)-7,9-ドデカジエン-1-イル アセテート（(E,E)-7,9-dodecadien-1-yl acetate）+SX、(Z,E)-9,12-テトラデカジエン-1-イル アセテート（(Z,E)-9,12-tetradecadien-1-yl acetate）+SX、(Z,E)-9,11-テトラデカジエン-1-イル アセテート（(Z,E)-9,11-tetradecadien-1-yl acetate）+SX、(Z,E)-7,11-ヘキサデカジエン-1-イル アセテート（(Z,E)-7,11-hexadecadien-1-yl acetate）+SX、(Z,Z)-3,13-オクタデカジエン-1-オール（(Z,Z)-3,13-octadecadien-1-ol）+SX、(Z,Z)-4,7-デカジエン-1-イル アセテート（(Z,Z)-4,7-decadien-1-yl acetate）+SX、（(Z,Z)-3,13-octadecadien-1-yl acetate）+SX、(Z,Z)-7,11-ヘキサデカジエン-1-イル アセテート（(Z,Z)-7,11-hexadecadien-1-yl acetate）+SX、(Z,Z,E)-7,11,13-ヘキサデカトリエナール（(Z,Z,E)-7,11,13-hexadecatrienal）+SX、(5R)-5-[(1Z)-1-デセン-1-イル]ジヒドロ-2(3H)-フラノン（(5R)-5-[(1Z)-1-decen-1-yl]dihydro-2(3H)-furanone）+SX、(2R,5R)-エチル-1,6-ジオキサスピロ[4.4]ノナン（(2R,5R)-ethyl-1,6-dioxaspiro[4,4]nonane）+SX、(2R,5S)-エチル-1,6-ジオキサスピロ[4.4]ノナン（(2R,5S)-ethyl-1,6-dioxaspiro[4,4]nonane）+SX、(4R,8R)-4,8-ジメチルデカナール（(4R,8R)-4,8-dimethyldecanal）+SX、(4R,8S)-4,8-ジメチルデカナール（(4R,8S)-4,8-dimethyldecanal）+SX、2,4-ジメチル-5-エチル-6,8-ジオキサビシクロ[3,2,1]オクタン(2,4-dimethyl-5-ethyl-6,8-dioxabicyclo[3,2,1]octane）+SX、(-)-4-メチル-3-ヘプタノール（(-)-4-methyl-3-heptanol）+SX、1,7-ジオキサスピロ[5,5]ウンデカン（1,7-dioxaspiro[5,5]undecane）+SX、3-カレン（3-carene）+SX、3-メチルシクロヘキサ-2-エン-1-オン（3-methylcyclohex-2-en-1-one）+SX、14-メチルオクタデカ-1-エン（14-methyloctadec-1-ene）+SX、4-メチルノナン-5-オール（4-methylnonan-5-ol）+SX、4-メチルノナン-5-オン（4-methylnonan-5-one）+SX、4-(3-オキソブチル)フェニル アセテート（4-(3-oxobutyl)phenyl acetate）+SX、ドデシル アセテート（dodecyl acetate）+SX、ドデカ-8,10-ジエン-1-イル アセテート（dodeca-8,10-dien-1-yl acetate）+SX、(2E,4Z)-デカジエン酸エチル（ethyl (2E,4Z)-decadienoate）+SX、4-メチルオクタン酸エチル（ethyl 4-methyloctanoate）+SX、2,6,10-トリメチルドデカン酸メチル（methyl 2,6,10-trimethyldodecanoate）+SX、テトラデカン-1-オール（tetradecan-1-ol）+SX、テトラデカ-11-エン-1-オール（tetradec-11-en-1-ol）+SX、テトラデカ-11-エン-1-イル アセテート（tetradec-11-en-1-yl acetate）+SX、トリデカ-4-エン-1-イル アセテート（tridec-4-en-1-yl acetate）+SX、(3S,6R)-3-メチル-6-イソプロペニル-9-デセン-1-イル アセテート（(3S,6R)-3-methyl-6-isopropenyl-9-decen-1-yl acetate）+SX、（(3S,6S)-3-メチル-6-イソプロペニル-9-デセン-1-イル アセテート（(3S,6S)-3-methyl-6-isopropenyl-9-decen-1-yl acetate））+SX、アルファ－マルチストリアチン（alpha-multistriatin）+SX、アルファ－ピネン（alpha-pinene）+SX、エンド－ブレビコミン（endo-brevicomin）+SX、エキソ－ブレビコミン（exo-brevicomin）+SX、カンフェン（camphene）+SX、コドレルア（codlelure）+SX、コドレモン（codlemone）+SX、キュウルア（cuelure）+SX、ディスパールア（disparlure）+SX、ドミニカルア（dominicalure）+SX、オイゲノール（eugenol）+SX、ファルネソール（farnesol）+SX、フェロルア（ferrolure）+SX、フロンタリン（frontalin）+SX、ゴシップルア（gossyplure）+SX、グランドルア（grandlure）+SX、グランドルアI（grandlure I）+SX、グランドルアII（grandlure II）+SX、グランドルアIII（grandlure III）+SX、グランドルアIV（grandlure IV）+SX、ヘキサルア（hexalure）+SX、イプスジエノール（ipsdienol）+SX、イプセノール（ipsenol）+SX、ジャポニルア（japonilure）+SX、リネアチン（lineatin）+SX、リトルア（litlue）+SX、ループルア（looplure）+SX、メドルア（medlure）+SX、メガトモ酸（megatomoic acid）+SX、メチルオイゲノール（methyl eugenol）+SX、ムスカルア（muscalure）+SX、ネロリドール（nerolidol）+SX、オルフラルア（orfralure）+SX、オリクタルア（oryctalure）+SX、オストラモン（ostramone）+SX、リンコルア（rhyncolure)+SX、シグルア(siglure)+SX、ソルジジン（sordidin）+SX、スルカトール（sulcatol）+SX、トリメドルア（trimedlure）+SX、トリメドルアＡ（trimedlure A）+SX、トリメドルアＢ1（trimedlure B1）+SX、トリメドルアＢ2（trimedlure B2）+SX、トリメドルアＣ（trimedlure C）+SX、トランク－コール（trunc-call）+SX、（E）－バーベノール（(E)-verbenol）+SX、（Z）－バーベノール（(Z)-verbenol）+SX、トランス－バーベノール（trans-verbenol）+SX、S－バーベノン（(S)-verbenone）+SX。 Combinations of the present component of the above group (h) with the compound of the present invention:
(E) -2-hexanal ((E) -2-hexenal) + SX, (E) -2-octadecenal ((E) -2-octadecenal) + SX, (E) -4-tridecene-1-yl acetate ((E) -4-tridecen-1-yl acetate) + SX, (E) -5-decen-1-yl acetate ((E) -5-decen-1-yl acetate) + SX, (E)- 5-decene-1-ol ((E) -5-decen-1-ol) + SX, (E) -3,3-dimethylcyclohexylideneacetaldehyde ((E) -3,3-dimethylcyclohexylideneacetaldehyde) + SX, (E) -7-dodecen-1-yl acetate ((E) -7-dodecen-1-yl acetate) + SX, (E) -8-dodecen-1-yl acetate ((E) -8-dodecen- 1-yl acetate) + SX, (E) -9-dodecen-1-yl acetate ((E) -9-dodecen-1-yl acetate) + SX, (E) -10-hexadecenal ((E) -10 -hexadecenal) + SX, (E) -11-hexadecen-1-yl acetate ((E) -11-hexadecen-1-yl acetate) + SX, (E) -11-tetradecen-1-yl acetate ((E) )-11-tetradecen-1-yl acetate) + SX, (E) -11-tetradecen-1-ol ((E) -11-tetradecen-1-ol + SX, (E) -4-tridecen-1-yl acetate ((E) -4-tridecen-1-yl acetate) + SX, (E) -6-methylhept-2-en-4-ol (E) -6-methylhept-2-en-4-ol) + SX, (Z) -2- (3,3-dimethylcyclohexylidene) ethanol ((Z) -2- (3,3-dimethylcyclohexylidene) ethanol + SX, (Z) -4-decen-1-yl acetate ((Z) -4-decen-1-yl acetate) + SX, (Z) -4-tridecene-1-yl acetate ((Z) -4-tridecen-1-yl acetate) + SX, (Z) -5-decen-1-yl acetate ((Z) -5-decen-1-yl acetate) + SX, (Z) -5-decene- 1-ol ((Z) -5-decen-1-ol) + SX, (Z) -7-tetradecenal ((Z) -7-tetradecenal) + SX, (Z) -7-dodecene-1-yl acetate ((Z) -7-dodecen-1-yl acetate) + SX, (Z) -8-dodecen-1-yl acetate ((Z) -8-dodecen-1-yl acetate) + SX, (Z)- 9-dodecen-1-yl acetate ((Z) -9-dodecen-1-yl acetate) + SX, (Z) -8-dodecen-1-ol ((Z) -8-dodecen-1-ol) + SX, (Z) -9-hexadecenal ((Z) -9-hexad ecenal) + SX, (Z) -10-hexadecen-1-yl acetate ((Z) -10-hexadecen-1-yl acetate) + SX, (Z) -11-hexadecen-1-ol ((Z)- 11-hexadecen-1-ol) + SX, (Z) -11-hexadecenal ((Z) -11-hexadecenal) + SX, (Z) -11-hexadecen-1-yl acetate ((Z) -11-hexadecen -1-yl acetate) + SX, (Z) -11-octadecenal ((Z) -11-octadecenal) + SX, (Z) -13-octadecenal ((Z) -13-octadecenal) + SX, (Z) -Hexadeca-13-en-1-yl acetate ((Z) -hexadec-13-en-11-yn-1-yl acetate) + SX, (Z) -13-octadecenal ((Z) -13-octadecenal) + SX, (Z) -icosa-13-en-10-one ((Z) -icos-13-en-10-one) + SX, (Z) -7-tetradecenal ((Z) -7-tetradecenal) + SX, (Z) -tetradec-9-en-1-ol ((Z) -tetradec-9-en-1-ol) + SX, (Z) -9-tetradecen-1-yl acetate ((Z) -9-tetradecen-1-yl acetate) + SX, (Z) -11-tetradecen-1-yl acetate ((Z) -11-tetradecen-1-yl acetate) + SX, (Z) -13-icosene-10-one ((Z) -13-icosen-10-one) + SX, (Z, E) -7,11-hexadecadien-1-yl acetate ((Z, E) -7 , 11-hexadecadien-1-yl acetate) + SX, (Z, E) -9,12-tetradecadien-1-yl acetate ((Z, E) -9,12-tetradecadien-1-yl acetate) + SX, (E, Z) -4,10-tetradecadien-1-yl acetate ((E, Z) -4,10-tetradecadadien-1-yl acetate) + SX, (E, E) -8,10 -Dodecadien-1-ol ((E, E) -8,10-dodecadien-1-ol) + SX, (E, E) -10,12-hexadecadienal ((E, E) -10,12 -hexadecadienal) + SX, (E, E) -9,11-tetradecadien-1-yl acetate ((E, E) -9,11-tetradecadadien-1-yl acetate) + SX, (E, Z) -2,13-octadecadien-1-ol ((E, Z) -2,13-octadecadien-1-ol) + SX, (E, Z) -3,13-octadecadien-1-ol ( (E, Z) -3,13-octadecadien-1-ol) + SX, (E, Z) -2,13-octadecadien-1-yl acetate ((E, Z) -2,13-octadecadien- 1-yl acetate) + SX, (E, Z) -3,13-octadecadien-1-yl acetate ((E, Z) ) -3,13-octadecadien-1-yl acetate) + SX, (E, Z) -7,9-dodecadien-1-yl acetate ((E, Z) -7,9-dodecadien-1-yl acetate) + SX, (E, E) -7,9-dodecadien-1-yl acetate ((E, E) -7,9-dodecadien-1-yl acetate) + SX, (Z, E) -9,12- Tetradecadien-1-yl acetate ((Z, E) -9,12-tetradecadien-1-yl acetate) + SX, (Z, E) -9,11-tetradecadien-1-yl acetate ((Z, E) , E) -9,11-tetradecadien-1-yl acetate) + SX, (Z, E) -7,11-hexadecadien-1-yl acetate ((Z, E) -7,11-hexadecadien-1 -yl acetate) + SX, (Z, Z) -3,13-octadecadien-1-ol ((Z, Z) -3,13-octadecadien-1-ol) + SX, (Z, Z)- 4,7-decadien-1-yl acetate ((Z, Z) -4,7-decadien-1-yl acetate) + SX, ((Z, Z) -3,13-octadecadien-1-yl acetate) + SX, (Z, Z) -7, 11-hexadecadien-1-yl acetate ((Z, Z) -7, 11-hexadecadien-1-yl acetate) + SX, (Z, Z, E) -7 , 11, 13-hexadecatrienal ((Z, Z, E) -7, 11, 13-hexadecatrinal) + SX, (5R) -5-[( 1Z) -1-Decen-1-yl] dihydro-2 (3H) -furanone ((5R) -5-[(1Z) -1-decen-1-yl] dihydro-2 (3H) -furanone) + SX , (2R, 5R) -ethyl-1,6-dioxaspiro [4.4] nonane ((2R, 5R) -ethyl-1,6-dioxaspiro [4,4] nonane) + SX, (2R, 5S) -ethyl- 1,6-dioxaspiro [4.4] nonane ((2R, 5S) -ethyl-1,6-dioxaspiro [4,4] nonane) + SX, (4R, 8R) -4,8-dimethyldecanal ((4R, 8R) -4,8-dimethyldecanal) + SX, (4R, 8S) -4,8-dimethyldecanal ((4R, 8S) -4,8-dimethyldecanal) + SX, 2,4-dimethyl-5-ethyl -6,8-Dioxabicyclo [3,2,1] octane (2,4-dimethyl-5-ethyl-6,8-dioxabicyclo [3,2,1] octane) + SX, (-)-4- Methyl-3-heptanol ((−)-4-methyl-3-heptanol) + SX, 1,7-dioxaspiro [5,5] undecane (1,7-dioxaspiro [5,5] undecane) + SX, 3- 3- Carene (3-carene) + SX, 3-methylcyclohex-2-en-1-one + SX, 14-methyloctadec-1-ene (14- methyloctadec-1-ene) + SX, 4-methylnonan-5-ol 4-methylnonan-5-ol) + SX, 4-methylnonan-5-one + SX, 4- (3-oxobutyl) phenyl acetate (4- (3-oxobutyl) phenyl acetate) + SX, dodecyl acetate + SX, dodeca-8,10-dien-1-yl acetate (dodeca-8,10-dien-1-yl acetate) + SX, ethyl (2E, 4Z) -decadecanoate (Ethyl (2E, 4Z) -decadienoate) + SX, ethyl 4- methyloctanoate (S-ethyl 4- methyloctanoate) + SX, methyl 2, 6, 10- trimethyldodecanoate (methyl 2, 6, 10-trimethyldodecanoate) + SX , Tetradecan-1-ol (tetradecan-1-ol) + SX, tetradec-11-en-1-ol (tetradec-11-en-1-ol) + SX, tetradeca-11-en-1-yl acetate ( tetradec-11-en-1-yl acetate) + SX, tridec-4-en-1-yl acetate (tridec-4-en-1-yl acetate) + SX, (3S, 6R) -3-methyl-6 -Isopropenyl-9-decen-1-yl acetate ((3S, 6R) -3-methyl-6-isopropenyl-9-decen-1-yl acetate) + SX, (3S, 6S) -3-Methyl-6-isopropenyl-9-decen-1-yl acetate ((3S, 6S) -3-methyl-6-isopropenyl-9-decen-1-yl acetate)) + SX Alpha-multistriatin (alpha-multistriatin) + SX, alpha-pinene (alpha-pinene) + SX, end-brevicomin (endo-brevicomin) + SX, exo-brevicomin (exo-brevicomin) + SX, camphene (camphene) ) + SX, coddle lure + SX, cod lemone + SX, cuelure + SX, disparlure + SX, dominicalure + SX, eugenol (eugenol) + SX, farnesol (farnesol) ) + SX, ferrolure + SX, frontalin + SX, gossyplure + SX, grandlure (grandlure) + SX, grandlure I (grandlure I) + SX, grandlure II (grandlure II) + SX, grandlure III (grandlure III) + SX, grandlure IV (grand lure IV) + SX, Hexalure + SX, Ips Dienol (ips dienol) + SX, Ipsenol (ipsenol) + SX, japonilure + SX, Lineatin + SX, Little A (litlue) + SX, Loop lure + SX, medlure + SX, megatomoic acid + SX, methyl eugenol + SX, muscalure + musk SX, nerolidol + nerolidol + SX, orfral ) + SX, oryctalure + SX, ostrumone (Ostramone) + SX, lycor (rhyncolure) + SX, siglure (siglure) + SX, soldidin (sordidin) + SX, sulcatol (sulcatol) + SX, trimedlure (trimedlure) + SX, trimedlure A + SX, trimedlure B1 + SX, trimedlure B2 + SX, trimedlure C + SX, trunk-call (trunc-call) + SX, ( E)-Verbenole ((E)-Verbanol) + SX, (Z)-Verbenole ((Z)-Verbenol) + SX, trans-Verbenole (trans-Verbenol) + SX, S-Verbenone ((S)-Verbenone) + SX.
　本発明化合物と本成分との比は、特に限定されるものではないが、重量比（本発明化合物：本成分）で１,０００：１～１：１,０００、５００：１～１：５００、１００：１～１：１００、５０：１～１：５０、２０：１～１：２０、１０：１～１：１０、３：１～１：３、１：１～１：５００、１：１～１：１００、１：１～１：５０、１：１～１：２０、１：１～１：１０等が挙げられる。 The ratio of the compound of the present invention to the component is not particularly limited, but the weight ratio (the compound of the present invention: this component) is 1,000: 1 to 1: 1,000, 500: 1 to 1: 500. 100: 1 to 1: 100, 50: 1 to 1:50, 20: 1 to 1:20, 10: 1 to 1:10, 3: 1 to 1: 3, 1: 1 to 1: 500, 1 And the like: 1: 1 to 1: 100, 1: 1 to 1:50, 1: 1 to 1:20, 1: 1 to 1:10, and the like.
　本発明化合物は、有害昆虫、有害ダニ類、有害線虫、及び有害軟体動物等の有害節足動物に対して効力を有する。有害節足動物としては、例えば以下のものが挙げられるが、これらに限定されるものではない。 The compounds of the present invention are effective against harmful arthropods such as harmful insects, harmful mites, harmful nematodes and harmful molluscs. Examples of harmful arthropods include, but are not limited to:
　半翅目害虫（Hemiptera）：ヒメトビウンカ（Laodelphax striatellus）、トビイロウンカ（Nilaparvata lugens）、セジロウンカ（Sogatella furcifera）、トウモロコシウンカ（Peregrinus maidis）、キタウンカ（Javesella pellucida）、クロフツノウンカ（Perkinsiella saccharicida）、Tagosodes orizicolus等のウンカ科（Delphacidae）；ツマグロヨコバイ（Nephotettix cincticeps）、タイワンツマグロヨコバイ（Nephotettix virescens）、クロスジツマグロヨコバイ（Nephotettix nigropictus）、イナズマヨコバイ（Recilia dorsalis）、チャノミドリヒメヨコバイ（Empoasca onukii）、ジャガイモヒメヨコバイ（Empoasca fabae）、コーンリーフホッパー（Dalbulus maidis）、シロオオヨコバイ（Cofana spectra）等のヨコバイ科（Cicadellidae）；Mahanarva posticata、Mahanarva fimbriolata等のコガシラアワフキムシ科（Cercopidae）；マメクロアブラムシ（Aphis fabae）、ダイズアブラムシ（Aphis glycines）、ワタアブラムシ（Aphis gossypii）、ヨーロッパリンゴアブラムシ（Aphis pomi）、ユキヤナギアブラムシ（Aphis spiraecola）、モモアカアブラムシ（Myzus persicae）、ムギワラギクオマルアブラムシ（Brachycaudus helichrysi）、ダイコンアブラムシ（Brevicoryne brassicae）、Rosy apple aphid（Dysaphis plantaginea）、ニセダイコンアブラムシ（Lipaphis erysimi）、チューリップヒゲナガアブラムシ（Macrosiphum euphorbiae）、ジャガイモヒゲナガアブラムシ（Aulacorthum solani）、レタスヒゲナガアブラムシ（Nasonovia ribisnigri）、ムギクビレアブラムシ（Rhopalosiphum padi）、トウモロコシアブラムシ（Rhopalosiphum maidis）、ミカンクロアブラムシ（Toxoptera citricida）、モモコフキアブラムシ（Hyalopterus pruni）、ヒエノアブラムシ（Melanaphis sacchari）、オカボノクロアブラムシ（Tetraneura nigriabdominalis）、カンシャワタアブラムシ（Ceratovacuna lanigera）、リンゴワタムシ（Eriosoma lanigerum）等のアブラムシ科（Aphididae）；ブドウネアブラムシ（Daktulosphaira vitifoliae）、Pecan phylloxera（Phylloxera devastatrix）、Pecan leaf phylloxera（Phylloxera notabilis）、Southern pecan leaf phylloxera（Phylloxera russellae）等のネアブラムシ科（Phylloxeridae）；ツガカサアブラムシ（Adelges tsugae）、Adelges piceae、ヒメカサアブラムシ（Aphrastasia pectinatae）等のカサアブラムシ科（Adelgidae）；イネクロカメムシ（Scotinophara lurida）、Malayan rice black bug（Scotinophara coarctata）、アオクサカメムシ（Nezara antennata）、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）、ムラサキシラホシカメムシ（Eysarcoris annamita）、クサギカメムシ（Halyomorpha halys）、ミナミアオカメムシ（Nezara viridula）、Brown stink bug（Euschistus heros）、Red banded stink bug（Piezodorus guildinii）、Oebalus pugnax、Dichelops melacanthus等のカメムシ科（Pentatomidae）；Burrower brown bug（Scaptocoris castanea）等のツチカメムシ科（Cydnidae）；ホソヘリカメムシ（Riptortus pedestris）、クモヘリカメムシ（Leptocorisa chinensis）、ホソクモヘリカメムシ（Leptocorisa acuta）等のホソヘリカメムシ科（Alydidae）；ホソハリカメムシ（Cletus punctiger）、アシビロヘリカメムシ（Leptoglossus australis）等のヘリカメムシ科（Coreidae）；カンシャコバネナガカメムシ（Caverelius saccharivorus）、コバネヒョウタンナガカメムシ（Togo hemipterus）、アメリカコバネナガカメムシ（Blissus leucopterus）等のナガカメムシ科（Lygaeidae）；アカヒゲホソミドリカスミカメ（Trigonotylus caelestialium）、アカスジカスミカメ（Stenotus rubrovittatus）、フタトゲムギカスミカメ（Stenodema calcarata）、サビイロカスミカメ（Lygus lineolaris）等のカスミカメムシ科（Miridae）；オンシツコナジラミ（Trialeurodes vaporariorum）、タバココナジラミ（Bemisia tabaci）、ミカンコナジラミ（Dialeurodes citri）、ミカントゲコナジラミ（Aleurocanthus spiniferus）、チャトゲコナジラミ（Aleurocanthus camelliae）、ヒサカキワタフキコナジラミ（Pealius euryae）等のコナジラミ科（Aleyrodidae）；シュロマルカイガラムシ（Abgrallaspis cyanophylli）、アカマルカイガラムシ（Aonidiella aurantii）、ナシマルカイガラムシ（Diaspidiotus perniciosus）、クワシロカイガラムシ（Pseudaulacaspis pentagona）、ヤノネカイガラムシ（Unaspis yanonensis）、ニセヤノネカイガラムシ（Unaspis citri）、等のマルカイガラムシ科（Diaspididae）；ルビーロウムシ（Ceroplastes rubens）等のカタカイガラムシ科（Coccidae）；イセリアカイガラムシ（Icerya purchasi）、キイロワタフキカイガラムシ（Icerya seychellarum）等のワタフキカイガラムシ科（Margarodidae）；ナスコナガイガラムシ（Phenacoccus solani）、クロテンコナカイガラムシ（Phenacoccus solenopsis）、フジコナカイガラムシ（Planococcus kraunhiae）、クワコナカイガラムシ（Pseudococcus comstocki）、ミカンコナカイガラムシ（Planococcus citri）、ガハニコナカイガラムシ（Pseudococcus calceolariae）、ナガオコナカイガラムシ（Pseudococcus longispinus）、タトルミーリーバグ（Brevennia rehi）等のコナカイガラムシ科（Pseudococcidae）；ミカンキジラミ（Diaphorina citri）、ミカントガリキジラミ（Trioza erytreae）、ナシキジラミ（Cacopsylla pyrisuga）、チュウゴクナシキジラミ（Cacopsylla chinensis）、ジャガイモトガリキジラミ（Bactericera cockerelli）、Pear psylla（Cacopsylla pyricola）等のキジラミ科（Psyllidae）；プラタナスグンバイ（Corythucha ciliata）、アワダチソウグンバイ（Corythucha marmorata）、ナシグンバイ（Stephanitis nashi）、ツツジグンバイ（Stephanitis pyrioides）等のグンバイムシ科（Tingidae）；トコジラミ（Cimex lectularius）等のトコジラミ科（Cimicidae）； Giant Cicada（Quesada gigas）等のセミ科（Cicadidae）及びブラジルサシガメ（Triatoma infestans）等のトリアトマ属（Triatoma spp.）の害虫。 Semi-lepidoptera (Hemiptera): Hemetobiunka (Laodelphax striatellus), Tobiirounka (Nilaparvata lugens), Sejirounka (Sogatella furcifera), Maize (Peregrinus maidis), Lobluntia (Javesella pellucida), Black-tailed Uchiluciculicus Leafhopper family (Delphacidae); green leafhopper (Nephotettix cincticeps), giant leafhopper green leafhopper (Nephotettix virescens), black leafhopper green leafhopper (Nephotettix nigropictus), green leafhopper leafworm (Recilia dorsalis), green leafhopper foliage ), Corn leaf hopper (Dalbulus maidis), white leafhopper (Cofana spectra), etc. (Cicadelidae); Mahanarva posticata, Mahanarva fimbriolata, etc. (Cercopidae) Aphids (Aphis fabae), soybean aphids (Aphis glycines), cotton aphids (Aphis gossypii), european apple aphids (Aphis pomi), pokeweed aphids (Aphis spiraecola), green peach aphid (Myzus persicae), (Brachycaudus helichrysi), Japanese radish aphid (Brevicoryne brassicae), Rosy apple aphid (Dysaphis plantaginea), pseudonymous aphid (Lipaphis erysimi), tulip rhinoceros aphid (Macrosipum euphorbirae), potato higate surface of a mouse ), Aphid beetle (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), red-handed aphid (Toxoptera citricida), a momocoffia aphid (Hyalopterus pruni) Aphids (Aphididae), such as aphids (Aphididae), such as a brown-headed aphid (Melanaphis sacchari), a black-backed aphid (Tetrananeura nigriabdominalis), a green-billed aphid (Ceratovacuna lanigera), and an apple cotton pea (Eriosoma lanigerum); Phylloxera devastatrix), Pecan leaf phylloxera (Phylloxera notabilis), Southern pecan leaf phylloxera (Phylloxera russellae), and the like (Phylloxeridae); Aphididae (Adelgidae); rice black bug (Scot inophara lurida), Malayan rice black bug (Scot inophara coarctata), green leaf bug (Nezara antennata), rhizophorid bug (Eysarcoris aeneus), giant leaf beetle (Eysarcoris lewisisi) , Eysarcoris ventralis, Eysarcoris anamita, Halyomorpha halys, Nezara viridula, Brown stink bug (Euschistus heros), Red banded stink bug (Pi. , Dichelops melacanthus and other Stinkidae (Pentatomidae); Burrower brown bug (Scaptocoris castanea) and other Sturgeon (Cydnidae); Etc. (Alydidae); Crustus punctiger (Cletus punctiger), Helicidae (Leptoglossus australis), etc. Helicidae (Coreidae); hemipterus), a Red-headed Bug family (Lygaeidae), such as Blissus leucopterus; Red-backed squirrels (Trigonotylus caelestialium), Red-backed snails (Stenotus rubrovittatus), Scutellaris moth (Stenotema calcarata), Myrtleidae (Miridae); Onion's Beak (Trialeurodes vaporariorum), B. tabaci (Bemisia tabaci), I. And so on) Whitefly (Aleyrodidae); White-backed scale insect (Abgrallapsis cyanophylli), Red-backed scale insect (Aonidiella aurantii), Nasi-maroon scaleworm (Diaspidiotus perniciosus), Musk Red-tailed beetles (Diaspididae), such as ruminants (Pseudaulacaspis pentagona), Red-winged beetles (Unaspis yanonensis), False-tailed scaled insects (Unaspis citri), etc .; Parchacia, Icarya seychellarum et al. (Margarodidae); P. cocci (Phenacoccus solani), P. cocci (Phenacoccus solenopsis), P. cocci (Planocccus kraunhiae) Pseudococcus comstocki), Anchovy (Planococcus citri), Anchovy (Pseudococcus calceolariae), Anchovy (Pseudococcus longispinus), Tutorum ree bug (Brevennia rehi), etc. Mushi family (Pseudococcidae); Psyllid (Diaphorina citri), Psyllidum (Trioza erytreae), Psyllid (Cacopsylla pyrisuga), Psyllid (Cacopsylla chinensis), Phytopathidae (Bactericera cockellicillus) Plantainidae (Tingidae), such as Psyllididae; Planitas gullby (Corythucha ciliata), Crustacean gurimbai (Corythucha marmorata), Nasigumbai (Stephanitis nashi), Stephanitis pyrioides, etc. (Tingidae); Cimicidae); Pests of Triatoma (Triatoma spp.) Such as the semi-family (Cicadidae) such as Giant Cicada (Quesada gigas) and the Brazilian red-handed turtle (Triatoma infestans).
　鱗翅目害虫（Lepidoptera）：ニカメイガ（Chilo suppressalis）、Darkheaded stem borer（Chilo polychrysus）、White stem borer（Scirpophaga innotata）、イッテンオオメイガ（Scirpophaga incertulas）、Rupela albina、コブノメイガ（Cnaphalocrocis medinalis）、Marasmia patnalis、イネハカジノメイガ（Marasmia exigua）、ワタノメイガ（Notarcha derogata）、アワノメイガ（Ostrinia furnacalis）、European corn borer（Ostrinia nubilalis）、ハイマダラノメイガ（Hellula undalis）、モンキクロノメイガ（Herpetogramma luctuosale）、シバツトガ（Pediasia teterrellus）、ライスケースワーム（Nymphula depunctalis）、Sugarcane borer（Diatraea saccharalis）等のツトガ科（Crambidae）；モロコシマダラメイガ（Elasmopalpus lignosellus）、ノシメマダラメイガ（Plodia interpunctella）、フタモンマダラノメイガ（Euzophera batangensis）等のメイガ科（Pyralidae）；ハスモンヨトウ（Spodoptera litura）、シロイチモジヨトウ（Spodoptera exigua）、アワヨトウ（Mythimna separata）、ヨトウガ（Mamestra brassicae）、イネヨトウ（Sesamia inferens）、シロナヨトウ（Spodoptera mauritia）、フタオビコヤガ（Naranga aenescens）、ツマジロクサヨトウ（Spodoptera frugiperda）、アフリカシロナヨトウ（Spodoptera exempta）、タマナヤガ（Agrotis ipsilon）、タマナギンウワバ（Autographa nigrisigna）、イネキンウワバ（Plusia festucae）、Soybean looper（Chrysodeixis includens）、トリコプルシア属（Trichoplusia spp.）、ニセアメリカタバコガ（Heliothis virescens）等のヘリオティス属（Heliothis spp.）、オオタバコガ（Helicoverpa armigera）、アメリカタバコガ（Helicoverpa zea）等のヘリコベルパ属（Helicoverpa spp.）、Velvetbean caterpillar（Anticarsia gemmatalis）、Cotton leafworm（Alabama argillacea）、Hop vine borer（Hydraecia immanis）等のヤガ科（Noctuidae）；モンシロチョウ（Pieris rapae）等のシロチョウ科（Pieridae）；ナシヒメシンクイ（Grapholita molesta）、スモモヒメシンクイ（Grapholita dimorpha）、マメシンクイガ（Leguminivora glycinivorella）、アズキサヤムシガ（Matsumuraeses azukivora）、リンゴコカクモンハマキ（Adoxophyes orana fasciata）、チャノコカクモンハマキ（Adoxophyes honmai）、チャハマキ（Homona magnanima）、ミダレカクモンハマキ（Archips fuscocupreanus）、コドリンガ（Cydia pomonella）、カンシャシンクイハマキ（Tetramoera schistaceana）、Bean Shoot Borer（Epinotia aporema）、Citrus fruit borer（Ecdytolopha aurantiana）等のハマキガ科（Tortricidae）；チャノホソガ（Caloptilia theivora）、キンモンホソガ（Phyllonorycter ringoniella）等のホソガ科（Gracillariidae）；モモシンクイガ（Carposina sasakii）等のシンクイガ科（Carposinidae）；Coffee Leaf miner（Leucoptera coffeella）、モモハモグリガ（Lyonetia clerkella）、ギンモンハモグリガ（Lyonetia prunifoliella）等のハモグリガ科（Lyonetiidae）；マイマイガ（Lymantria dispar）等のリマントリア属（Lymantria spp.）、チャドクガ（Euproctis pseudoconspersa）等のユープロクティス属（Euproctis spp.）等のドクガ科（Lymantriidae）；コナガ（Plutella xylostella）等のコナガ科（Plutellidae）；モモキバガ（Anarsia lineatella）、イモキバガ（Helcystogramma triannulella）、ワタアカミムシガ（Pectinophora gossypiella）、ジャガイモガ（Phthorimaea operculella）、Tuta absoluta等のキバガ科（Gelechiidae）；アメリカシロヒトリ（Hyphantria cunea）等のヒトリガ科（Arctiidae）；Giant Sugarcane borer（Telchin licus）等のカストニアガ科（Castniidae）；ヒメボクトウ（Cossus insularis）等のボクトウガ科（Cossidae）；ヨモギエダシャク（Ascotis selenaria）等のシャクガ科（Geometridae）；ヒロヘリアオイラガ（Parasa lepida）等のイラガ科（Limacodidae）；カキノヘタムシガ（Stathmopoda masinissa）等のニセマイコガ科（Stathmopodidae）；クロメンガタスズメ（Acherontia lachesis）等のスズメガ科（Sphingidae）；キクビスカシバ（Nokona feralis）、コスカシバ（Synanthedon hector）、ヒメコスカシバ（Synanthedon tenuis）等のスカシバガ科（Sesiidae）；イネツトムシ（Parnara guttata）等のセセリチョウ科（Hesperiidae）、イガ（Tinea translucens）、コイガ（Tineola bisselliella）等のヒロズコガ科（Tinedae）の害虫。 Lepidoptera insects (Lepidoptera): Nymphs (Chilo suppressalis), Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Itten's tree magnolia (Scirpophaga incertulas), Rupela albina, Kobomeiga (Cinatalitraceitraceitracel Red clover (Marasmia exigua), cotton dwarf (Notarcha derogata), African dwarf (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), black-legged moth (Hellula undulis), Monquil chronogare (Herpetogramma luctiguete) Rice case worms (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), etc. (Cambididae); (Pyralidae); Spodoptera litura, Spodoptera exigua, Mythimna separata, Mythosperma (Mamestra brassicae), Ladybug (Sesamia inferens), White-tailed Spurgeon (Spodobacterium) White-spotted spiderfish (Spodoptera frugiperda), African white-winged pea (Spodoptera exempta), pokeweed (Agrotis ipsilon), pokeweed wharf (Autographa nigrisigna), rice kinwa waba (Plusia festucae), Soybean looper (Chrysodeixis cul.) Heliothis sp. (Heliothis virescens), Heliothis spp., Helicoverpa armigera, Helicoverpa zea etc. Helicoverpa spp., Velvetbean caterpillar (Anticarsia) gemmatalis), Cotton leafworm (Alabama argillacea), Hop vine borer (Hydraecia immanis), etc .; Nocturidae (Noctuidae); dimorpha), legume mincing moth (Leguminivora glycinivorella), azuxamushi moth (Matsumuraeses azukivora), apple red pokemon mackerel (Adoxophyes orana fasciata), kanokokan monmai (Adoxophys honmai), chahamaki (Homona magnima trich.) (Cydia pomonella), Chinese chaff (Tetramoera schistaceana), Bean Shoot Borer (Epinotia aporema), Citrus fruit borer (Ecdytolopha aurantiana), and other family of torrididae (Tortricidae); Family Gracillariidae such as Goniella); Family Carposinidae (Carposinidae) such as Carposina sasakii; Coffee Leaf miner (Leucoptera coffeella); A member of the genus Lymantriidae (Lymantriidae) such as Lymantria sppar, such as Lymantria dispar, Euproctis pseudoconspersa, etc; (Plullidae); Psyllididae (Gelechiidae) such as peach moth (Anarsia lineatella), potato moth (Helcystogramma triannulella), cotton moth (Pectinophora gossy piella), potato moth (Phthorimaea operculella), Tuta absoluta etc. Arctiidae); Giant Sugarc Anemoneidae (Castniidae) such as Ane borer (Telchin licus); Bacteriidae (Cossidae) such as Cossus insularis etc .; Anemone family (Limacodidae); Anemoneidae (Stathmopoda masinissa), such as Stathmopodidae; Acherontia lachesis, such as Sphingidae (Sphingidae); Tenuis) et al. (Sesiidae); insects of the rice tortoise (Parnara guttata) et al., Hesperiidae, pests of the family Iridaceae (Tinedae) such as the liga (Tinea translucens), and the lichen (Tineola bisselliella).
　総翅目害虫（Thysanoptera）：ミカンキイロアザミウマ（Frankliniella occidentalis）、ミナミキイロアザミウマ（Thrips palmi）、チャノキイロアザミウマ（Scirtothrips dorsalis）、ネギアザミウマ（Thrips tabaci）、ヒラズハナアザミウマ（Frankliniella intonsa）、イネアザミウマ（Stenchaetothrips biformis）、モトジロアザミウマ（Echinothrips americanus）等のアザミウマ科（Thripidae）；イネクダアザミウマ（Haplothrips aculeatus）等のクダアザミウマ科（Phlaeothripidae）の害虫。 Thysanoptera: Thripsidae (Frankliniella occidentalis), Thrips palmi (Thrips palmi), Chalyss occidentalis (Scirtothrips dorsalis), Locustoids (Thrips tabaci), Philosophis japonicus (Frankliniella intimasite) ), Thripidae such as Echinothrips americanus etc .; Pests of the Thripsidae (Phlaeothripidae) such as Haekohrips aculeatus.
　双翅目害虫（Diptera）：タネバエ（Delia platura）、タマネギバエ（Delia antiqua）、テンサイモグリハナバエ（Pegomya cunicularia）等のハナバエ科（Anthomyiidae）；シュガービートルートマゴット（Tetanops myopaeformis）等のハネフリバエ科（Ulidiidae）；イネハモグリバエ（Agromyza oryzae）、トマトハモグリバエ（Liriomyza sativae）、マメハモグリバエ（Liriomyza trifolii）、ナモグリバエ（Chromatomyia horticola）等のハモグリバエ科（Agromyzidae）；イネキモグリバエ（Chlorops oryzae）等のキモグリバエ科（Chloropidae）；ウリミバエ（Bactrocera cucurbitae）、ミカンコミバエ（Bactrocera dorsalis）、ナスミバエ（Bactrocera latifrons）、オリーブミバエ（Bactrocera oleae）、クインスランドミバエ（Bactrocera tryoni）、チチュウカイミバエ（Ceratitis capitata）、アップルマゴット（Rhagoletis pomonella）、オウトウハマダラミバエ（Rhacochlaena japonica）等のミバエ科（Tephritidae）；イネヒメハモグリバエ（Hydrellia griseola）、トウヨウイネクキミギワバエ（Hydrellia philippina）、イネクキミギワバエ（Hydrellia sasakii）等のミギワバエ科（Ephydridae）；オウトウショウジョウバエ（Drosophila suzukii）等のショウジョウバエ科（Drosophilidae）；オオキモンノミバエ（Megaselia spiracularis）等のノミバエ科（Phoridae）；オオチョウバエ（Clogmia albipunctata）等のチョウバエ科（Psychodidae）；チビクロバネキノコバエ(Bradysia difformis)等のクロバネキノコバエ科（Sciaridae）；ヘシアンバエ（Mayetiola destructor）、イネノシントメタマバエ（Orseolia oryzae）等のタマバエ科（Cecidomyiidae）；Diopsis macrophthalma等のシュモクバエ科（Diopsidae）；キリウジガガンボ（Tipula aino）、Common cranefly（Tipula oleracea）、European cranefly（Tipula paludosa）等のガガンボ科（Tipulidae）、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）、シナハマダラ力（Anopheles hyracanus sinesis）、コガタアカイエカ（Culex quinquefasciatus）、チカイエ力（Culex pipiens molestus Forskal）、ネッタイイエカ（Culex quinquefasciatus）等のカ科（Culicidae）、キアシオオブユ（Prosimulium yezoensis）、ツメ卜ゲブユ（Simulium ornatum）等のブユ科（Simulidae）、ウシアブ（Tabanus trigonus)等のアブ科（Tabanidae）、イエバエ（Musca domestica）、オオイエバエ（Muscina stabulans）、サシバエ（Stomoxys calcitrans）、ノサシバエ（Haematobia irritans）等のイエバエ科（Muscidae）、クロバエ科（Calliphoridae）、ニクバエ科（Sarcophagidae）、オオユスリカ（Chironomus plumosus）、セスジユスリカ（Chironomus yoshimatsui）、ハイイロユスリカ（Glyptotendipes tokunagai）等のユスリカ科(Chironomidae）、ヒメイエバエ科（Fannidae）の害虫。 Insect pests of the order Diptera (Diptera): Seed fly (Delia platura), onion fly (Delia antiqua), sugar beet fly (Pegomya cunicularia), etc. (Anthomyiidae); Sugar beet root maggot (Tetanops myopaeformis) etc. ; Agrobacterium family (Agromyza oryzae), a tomato leafhopper (Liriomyza sativae), a rice leafminer fly (Liriomyza trifolii), a leafminer fly (Chromatomya horticola), and the like (Agromyzidae); (Bactrocera cucurbitae), Citrus fruit fly (Bactrocera dorsalis), Nassy fruit fly (Bactrocera latiphrons), Olive fruit fly (Bactrocera oleae), Quinceland fruit fly (Bactrocera tryoni), Citrus fruit fly (Ceratitis capitata) Tephritidae (Tephritidae), such as letis pomonella, sweet potato fruit fly (Rhacochlaena japonica), etc .; Ephydridae); Drosophila (Drosophila suzukii) etc .; Drosophila family (Drosophilidae); Brachysia dinermis) and other black fly mushroom flies (Sciridae); Hessy fly (Mayetiola destructor), inocylid fly (Orseolia oryzae) etc .; fruit fly (Cecidomyiidae);aline), Common cranefly (Tipula oleracea), European cranefly (Tipula paludosa), etc , Culex trique (Culex quinquefasciatus), Culex pipiens molestus Forskal, Culex quinque fasciatus such as Culicidae, Prosimulium yezoensis, Protelium riumnus Tabanidae (Tabanidae), such as Tabanis trigonus, housefly (Musca domestica), house fly (Muscina stabulans), house fly (Stomoxys calcitrans), house fly (Haematobia irritans), house fly family (Muscidae), Sarcophagidae, sweetfish Rika (Chironomus plumosus), Chironomus yoshimatsui (Chironomus yoshimatsui), Gray midge (Glyptotendipes tokunagai) Chironomidae such as (Chironomidae), pest of fanniidae (Fannidae).
　鞘翅目害虫（Coleoptera）：ウエスタンコーンルートワーム（Diabrotica virgifera virgifera）、サザンコーンルートワーム（Diabrotica undecimpunctata howardi）、ノザンコーンルートワーム（Diabrotica barberi）、メキシカンコーンルートワーム（Diabrotica virgifera zeae）、バンデッドキューカンバービートル（Diabrotica balteata）、Cucurbit Beetle（Diabrotica speciosa）、ビーンリーフビートル（Cerotoma trifurcata）、クビアカクビホソハムシ（Oulema melanopus）、ウリハムシ（Aulacophora femoralis）、キスジノミハムシ（Phyllotreta striolata）、Cabbage flea beetle(Phyllotreta cruciferae)、Western black flea beetle（Phyllotreta pusilla）、Cabbage stem flea beetle(Psylliodes chrysocephala)、コロラドハムシ（Leptinotarsa decemlineata）、イネドロオイムシ（Oulema oryzae）、グレープ・コラスピス（Colaspis brunnea）、コーン・フレアビートル（Chaetocnema pulicaria）、サツマイモヒサゴトビハムシ（Chaetocnema confinis）、ポテト・フレアビートル（Epitrix cucumeris）、イネトゲハムシ（Dicladispa armigera）、southern corn leaf beetle（Myochrous denticollis）、ヨツモンカメノコハムシ（Laccoptera quadrimaculata）、タバコノミハムシ（Epitrix hirtipennis）等のハムシ科（Chrysomelidae）；Seedcorn beetle（Stenolophus lecontei）、Slender seedcorn beetle（Clivina impressifrons）等のオサムシ科（Carabidae）；ドウガネブイブイ（Anomala cuprea）、ヒメコガネ（Anomala rufocuprea）、アオドウガネ（Anomala albopilosa）、マメコガネ（Popillia japonica）、ナガチャコガネ（Heptophylla picea）、European Chafer（Rhizotrogus majalis）、クロマルコガネ（Tomarus gibbosus）、Holotrichia属（Holotrichia spp.）、ジューン・ビートル（Phyllophaga crinita）等のPhyllophaga属（Phyllophaga spp.）、Diloboderus abderus等のDiloboderus属（Diloboderus spp.）等のコガネムシ科（Scarabaeidae）；ワタミヒゲナガゾウムシ（Araecerus coffeae）、アリモドキゾウムシ（Cylas formicarius）、イモゾウムシ（Euscepes postfasciatus）、アルファルファタコゾウムシ（Ｈypera postica）、コクゾウムシ（Sitophilus zeamais）、イネゾウムシ（Echinocnemus squameus）、イネミズゾウムシ（Lissorhoptrus oryzophilus）、シロスジオサゾウムシ（Rhabdoscelus lineatocollis）、ワタミハナゾウムシ（Anthonomus grandis）、シバオサゾウムシ（Sphenophorus venatus）、Southern Corn Billbug（Sphenophorus callosus）、Soybean stalk weevil（Sternechus subsignatus）、Sugarcane weevil（Sphenophorus levis）、サビヒョウタンゾウムシ（Scepticus griseus）、トビイロヒョウタンゾウムシ（Scepticus uniformis）、ブラジルマメゾウムシ（Zabrotes subfasciatus）、マツノキクイムシ（Tomicus piniperda）、Coffee Berry Borer（Hypothenemus hampei）、Aracanthus mourei等のAracanthus属（Aracanthus spp.）、cotton root borer(Eutinobothrus brasiliensis)等のゾウムシ科（Curculionidae）；コクヌストモドキ（Tribolium castaneum）、ヒラタコクヌストモドキ（Tribolium confusum）等のゴミムシダマシ科（Tenebrionidae）；ニジュウヤホシテントウ（Epilachna vigintioctopunctata）等のテントウムシ科（Coccinellidae）；ヒラタキクイムシ（Lyctus brunneus）等のナガシンクイムシ科（Bostrychidae）；ヒョウホンムシ科（Ptinidae）；ゴマダラカミキリ（Anoplophora malasiaca）、Migdolus fryanus等のカミキリムシ科（Cerambycidae）；オキナワカンシャクシコメツキ（Melanotus okinawensis）、トビイロムナボソコメツキ（Agriotes fuscicollis）、クシコメツキ（Melanotus legatus）、アシブトコメツキ属（Anchastus spp.）、コノデルス属（Conoderus spp.）、クテニセラ属（Ctenicera spp.）、リモニウス属（Limonius spp.）、Aeolus属（Aeolus spp.）等のコメツキムシ科（Elateridae）；アオバアリガタハネカクシ（Paederus fuscipes）等のハネカクシ科（Staphylinidae）、ヒメマルカツオブシムシ（Anthrenus verbasci）、ハラジロカツオブシムシ（Dermestes maculates)等のカツオブシムシ科（Dermestidae）、タバコシバンムシ（Lasioderma serricorne）、ジンサンシバンムシ（Stegobium paniceum）等のシバンムシ科（Anobidae）の害虫。 Coleoptera insect pest (Coleoptera): Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi), Northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), Banded Cucumber Beetle (Diabrotica virgifera zeae) Culibita beetle (Diabrotica balteata), Cucurbit Beetle (Diabrotica speciosa), Bean leaf beetle (Cerotoma trifurcata), Kubi カ ハ ム ハ ム (Oulema melanopus), ground leaf beetle (Aulacophora femoralis), キ ス ジ ハ ム Phylloteta striolate 、 tle ( black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado potato beetle (Leptinotarsa decemlineata), indremo oi moth (Oulema oryzae), grape colapice (Colaspis brunnea) ), Corn flare beetle (Chaetocnema pulicaria), sweet potato beetle (Chaetocnema confinis), potato flare beetle (Epitrix cucumeris), red leaf beetle (Dicladispa armigera), southern corn leaf beetle (Myochrous denticophila) ), The leaf beetle family (Chrysomelidae) such as tobacco flea beetle (Epitrix hirtipennis); Seedcorn beetle (Stenolophus lecontei); , Anomalu albapilosa, Popillia japonica, Heptophylla picea, European Chafer (Rhizotrogus majalis), Black marlin (Tomarus gibbosus), Holotrichia sp. Phyllophaga (Phyllophaga spp.) such as Haga crinita, Scarabaeidae (Scarabaeidae) such as Diloboderus (Diloboderus spp.) such as Diloboderus abderus; Euscepes postfasciatus), alfalfate weevil (Hypera postica), tree weevil (Sitophilus zeamais), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), Shirosuio sage beetle (Rhabdoscelus lineate history) Sphenophorus venatus), Southern Corn Billbug (Sphenophorus callosus), Soybean stalk weevil (Sternechus subsignatus), Sugarcane weevil (Sphenophorus levis), Crustacean weevil (Scepticus griseus), Tobiiro gourd (Scepticus unifors) mis), Brazilian bean weevil (Zabrotes subfasciatus), Pinus bovis (Tomicus piniperda), Coffee Berry (Hypothenemus hampei), Aracanthus sp., such as Aracanthus mourei et al. ; Tricholium castaneum, Tricholium confusum (Tenebrionidae) such as Tricholium castaneum, Tribolium condusum (Tenebrionidae); Etirachnida (Coccinellidae) such as Epilachna vigintopoc unctata, etc .; Family (Bostrychidae); Streptomyces (Ptinidae); Anemone longhorn (Anoplophora malasiaca), Migdolus fryanus etc. Long-horned family (Cerambycidae); , Melon (Melanotus legatus), Bacteroides (Anchastus spp.), Conoderus spp., Ctenicera spp., Limonius sp., Aeolus sp. (Elateridae); Staphylinidae (Staphylinidae), such as Paederus leaf beetle (Paederus fuscipes); Pests of the Anemonidae family (Anobidae) such as ginseng beetle (Stegobium paniceum).
　直翅目害虫（Orthoptera）：トノサマバッタ（Locusta migratoria）、モロッコトビバッタ（Dociostaurus maroccanus）、オーストラリアトビバッタ（Chortoicetes terminifera）、アカトビバッタ（Nomadacris septemfasciata）、Brown Locust（Locustana pardalina）、Tree Locust（Anacridium melanorhodon）、Italian Locust（Calliptamus italicus）、Differential grasshopper（Melanoplus differentialis）、Two striped grasshopper（Melanoplus bivittatus）、Migratory grasshopper（Melanoplus sanguinipes）、Red-Legged grasshopper（Melanoplus femurrubrum）、Clearwinged grasshopper（Camnula pellucida）、サバクワタリバッタ（Schistocerca gregaria）、Yellow-winged locust（Gastrimargus musicus）、Spur-throated locust（Austracris guttulosa）、コバネイナゴ（Oxya yezoensis）、ハネナガイナゴ（Oxya japonica）、タイワンツチイナゴ（Patanga succincta）等のバッタ科（Acrididae）；ケラ（Gryllotalpa orientalis）等のケラ科（Gryllotalpidae）；ヨーロッパイエコオロギ（Acheta domestica）、エンマコオロギ（Teleogryllus emma）等のコオロギ科（Gryllidae）；Mormon cricket（Anabrus simplex）等のキリギリス科（Tettigoniidae）の害虫。 Orthopteran pests (Orthoptera): Toocta grasshoppers (Locusta migratoria), Toroca grasshoppers (Dociostaurus maroccanus), Australian Tobetta grass (Chortoicetes terminifera), Red-footed grasshoppers (Nomadacris septemfasciata), Brown Locust (Locustana palligates) Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipelus), Red-Legged grasshopper (Melh gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Kobayinago (Oxya yezoensis), Hanekinainago (Oxya japonica), Trichoderma japonicus (Patanga succincta), etc. rididae); cricket (Gryllotalpa orientalis) cricket family (Gryllotalpidae); european cricket (Acheta domestica); pest.
　膜翅目害虫（Hymenoptera）：カブラハバチ（Athalia rosae）、ニホンカブラバチ（Athalia japonica）等のハバチ科（Tenthredinidae）；ヒアリ（Solenopsis invicta）、アカカミアリ（Solenopsis geminata）等のトフシアリ属（Solenopsis spp.）、Brown leaf-cutting ant（Atta capiguara）等のハキリアリ属（Atta spp.)、ヒメハキリアリ属（Acromyrmex spp.）、サシハリアリ(Paraponera clavata)、ルリアリ（Ochetellus glaber）、イエヒメアリ（Monomorium pharaonis）、アルゼンチンアリ（Linepithema humile）、クロヤマアリ(Formica fusca japonica)，アミメアリ(Pristomyrmex punctutus)，オオズアリ(Pheidole noda)、ツヤオオズアリ（Pheidole megacephala）、クロオオアリ（Camponotus japonicus）、ムネアカオオアリ（Camponotus obscuripes）等のオオアリ属、オキシデンタリスシュウカクアリ（Pogonomyrmex occidentalis）等のシュウカクアリ属（Pogonomyrmex）、コカミアリ（Wasmania auropunctata）等のコカミアリ属（Wasmania）、アシナガキアリ（Anoplolepis gracilipes）等のアリ科（Formicidae）、オオスズメバチ（Vespa mandarinia japonica）、ケブカスズメバチ（Vespa simillima）、コガタスズメバチ（Vespa analis Fabriciusi）、ツマアカスズメバチ（Vespa velutina）、セグロアシナガバチ（Polistes jokahamae）等のスズメバチ科（Vespidae）、モミノオオキバチ（Urocerus gigas）等のキバチ科（Siricidae）、アリガタバチ科（Bethylidae）の害虫。 Hymenoptera pests (Hymenoptera): Japanese gossips (Athalia rosae), Japanese black-billed wasps (Athalia japonica), etc. (Tenthredinidae); Brown leaf-cutting ant (Atta capiguara), etc., Atta spp., Acromyrmex spp., Paraponera clavata, Rucheli (Ochetellus glaber), Houseworm (Monomorium pharaonis), Argentine Ali (Linepithema) humile), black rock ants (Formica fusca japonica), short-necked ants (Pheidole noda), horned ants (Pheidole megacephala), black-necked ants (Camponotus japonicus), red-winged great ants (Camponotus obculipes), etc. Ali (Pogonomyrmex occidentalis) etc Anemone family (Pagonomyrmex), an earthworm (Wasmania auropunctata), etc., a genus of earthworm (Wasmania), a family of an ant family (Formicidae) such as a green leaf ant (Anoplolepis gracilipes), a giant hornbill (Vespa manadinia japonica), an anemone carp Vespha anilis Fabriciusi, Vespa velutina, Polistes jokahamae, etc., Hornetidae (Vespidae), Momin's giant bee (Urocerus gigas) etc. Psyllididae (Siricidae), Arigatidae pests
　ゴキブリ目害虫（Blattodea）：チャバネゴキブリ（Blattella germanica）等のチャバネゴキブリ科（Blattellidae）；クロゴキブリ（Periplaneta fuliginosa）、ワモンゴキブリ（Periplaneta americana）、トビイロゴキブリ（Periplaneta brunnea）、トウヨウゴキブリ（Blatta orientalis）等のゴキブリ科（Blattidae）；ヤマトシロアリ（Reticulitermes speratus）、イエシロアリ（Coptotermes formosanus）、アメリカカンザイシロアリ（Incisitermes minor）、ダイコクシロアリ（Cryptotermes domesticus）、タイワンシロアリ（Odontotermes formosanus）、コウシュンシロアリ（Neotermes koshunensis）、サツマシロアリ（Glyptotermes satsumensis）、ナカジマシロアリ（Glyptotermes nakajimai）、カタンシロアリ（Glyptotermes fuscus）、オオシロアリ（Hodotermopsis sjostedti）、コウシュウイエシロアリ（Coptotermes guangzhouensis）、アマミシロアリ（Reticulitermes amamianus）、ミヤタケシロアリ（Reticulitermes miyatakei）、カンモンシロアリ（Reticulitermes kanmonensis）、タカサゴシロアリ（Nasutitermes takasagoensis）、ニトベシロアリ（Pericapritermes nitobei）、ムシャシロアリ（Sinocapritermes mushae）、Cornitermes cumulans等のシロアリ科（Termitidae）の害虫。 Cockroach second order (Blattodea): German cockroach (Blattella germanica) and other German cockroaches (Blattellidae); Family (Blattidae); Yamato termites (Reticulitermes speratus), German termites (Coptotermes formosanus), American termites (Incisitermes minor), Dixtermite termites (Cryptotermes domesticus), Tiwanite termites (Odontotermes formosanus), Origami termites (Glyptotermes satsumensis), Phytotermite (Glyptotermes nakajimai), Catan termite (Glyptotermes fuscus), Giant termite (Hodotermopsis sjostedti), Phytotermite (Coptotermes guangzhouen) sis), Amabi termite (Reticulitermes amamianus), Mamitake termite (Reticulitermes miyatakei), Cammon termite (Reticulitermes kanmonensis), Takasago termite (Nasutitermes takasagoensis), Nitobe termite (Pericapritermes nitobei), Musashi termitimates Pest of termite family (Termitidae).
　ノミ目害虫（Siphonaptera）:ネコノミ（Ctenocephalidae felis）、イヌノミ（Ctenocephalides canis）、ヒ卜ノミ（Pulex irritans）、ケオプスネズミノミ（Xenopsylla cheopis）、スナノミ（Tunga penetrans）、ニワトリノミ（Echidnophaga gallinacea）、ヨーロッパネズミノミ（Nosopsyllus fasciatus）等の害虫。 Flea order pest (Siphonaptera): cat flea (Ctenocephalidae felis), dog flea (Ctenocephalides canis), cypress flea (Pulex irritans), pheasant flyfish (Xenopsylla cheopis), sunaw tree (Tunga penetrans), chick flea (Echidnophaga gallinacea) Pests such as mouse fleas (Nosopsyllus fasciatus).
　シラミ目害虫（Anoplura）：ブタジラミ（Haematopinus suis）、ウシジラミ（Haematopinus eurysternus）、ヒツジシラミ(Dalmalinia ovis)、イヌジラミ（Linognathus seypsus）、ヒトジラミ（Pediculus humanis）、コロモジラミ（Pediculuc humanus corporis）、アタマジラミ（Pediculus humanus humanus）、ケジラミ (Phthirus pubis)等の害虫。 Pests Lice (Anoplura): pig lice (Haematopinus suis), lice (Haematopinus eurysternus), sheep lice (Dalmalinia ovis), lice (Linognathus seypsus), lice lice (Pediculus humanis), body lice (Pediculucus humanus corporis) , Pests such as white-tailed lice (Phthirus pubis).
　ハジラミ目害虫（Mallophagida）：ウシハジラミ（Dalmalinia bovis）、ヒツジハジラミ（Dalmalinia ovis）等のボビコーラ属（Bovicola spp.）；イヌハジラミ（Trichodectes canis）等のケモノハジラミ属（Trichodectes spp.）、ネコハジラミ（Felicola subrostrata）等のフェリコラ属（Felocpla spp）、ニワトリナガハジラミ(Lipeurus caponis)等のペウルス属（Lipeurus spp.）、トリメノポン属（Trimenopon spp）、メノポン属(Menopon spp.)等のトリハジラミ科（Menoponidae）等の害虫。 Psyllid pests (Mallophagida): Bovine flea (Dalmalinia bovis), sheep flea (Dalmalinia ovis) etc. Bovicola sp. (Bovicola spp.); Et al. (Felocpla spp), chicken long-tailed lice (Lipeurus caponis) etc. Peurus (Lipeurus spp.), Trimenopon sp. (Trimenopon spp), Menopon spp. Etc. pests of the family Tricholaridae (Menoponidae) .
　ダニ目害虫（Acari）：ナミハダニ（Tetranychus urticae）、カンザワハダニ（Tetranychus kanzawai）、ミツユビナミハダニ（Tetranychus evansi）、ミカンハダニ（Panonychus citri）、リンゴハダニ（Panonychus ulmi）、オリゴニカス属（Oligonychus spp.）等のハダニ科（Tetranychidae）；ミカンサビダニ（Aculops pelekassi）、リュウキュウミカンサビダニ（Phyllocoptruta citri）、トマトサビダニ（Aculops lycopersici）、チャノサビダニ（Calacarus carinatus）、チャノナガサビダニ（Acaphylla theavagrans）、ニセナシサビダニ（Eriophyes chibaensis）、リンゴサビダニ（Aculus schlechtendali）、カキサビダニ（Aceria diospyri）、Aceria tosichella、シソサビダニ（Shevtchenkella sp.）等のフシダニ科（Eriophyidae）；チャノホコリダニ（Polyphagotarsonemus latus）等のホコリダニ科（Tarsonemidae）；ミナミヒメハダニ（Brevipalpus phoenicis）等のヒメハダニ科（Tenuipalpidae）；ケナガハダニ科（Tuckerellidae）；フタトゲチマダニ（Haemaphysalis longicornis）、キチマダニ（Haemaphysalis flava）、タイワンカクマダニ（Dermacentor taiwanensis）、アメリカイヌカクマダニ（Dermacentor variabilis）、デルマセントル・アンデルソニ（Dermacentor andersoni）、ヤマトマダニ（Ixodes ovatus）、シュルツマダニ（Ixodes persulcatus）、イクソデス・リシナス（Ixodes ricinus）、ブラックレッグドチック（Ixodes scapularis）、アメリカキララマダニ（Amblyomma americanum）、アンブリオンマ・マクラタム（Ambryomma maculatum）、オウシマダニ（Boophilus microplus）、ブーフィラス・アンヌラタス（Boophilus annulatus）、クリイロコイタマダニ（Rhipicephalus sanguineus）等のマダニ科（Ixodidae）；ケナガコナダニ（Tyrophagus putrescentiae）、ホウレンソウケナガコナダニ（Tyrophagus similis）等のコナダニ科（Acaridae）；コナヒョウヒダニ（Dermatophagoides farinae）、ヤケヒョウヒダニ（Dermatophagoides pteronyssinus）等のチリダニ科（Pyroglyphidae）；ホソツメダニ（Cheyletus eruditus）、クワガタツメダニ（Cheyletus malaccensis）、ミナミツメダニ（Cheyletus moorei）、イヌツメダニ（Cheyletiella yasguri）等のツメダニ科（Cheyletidae）；ミミヒゼンダニ（Otodectes cynotis）、ヒゼンダニ（Sarcoptes scabiei）等のヒゼンダニ科（Sarcoptidae）；イヌニキビダニ（Demodex canis）等のニキビダニ科（Demodicidae）；ズツキダニ科（Listrophoridae）；イエササラダニ科（Haplochthoniidae）；イエダニ（Ornithonyssus bacoti）、トリサシダニ（Ornithonyssus sylviarum）等のオオサシダニ科（Macronyssidae）；ワクモ（Dermanyssus gallinae）等のワクモ科（Dermanyssidae）；アカツツガムシ（Leptotrombidium akamushi）等のツツガムシ科（Trombiculidae）の害虫。 Acarid pests (Acari): Two-spotted spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai), Mitosuban spider mite (Tetranychus evansi), Citrus red spider mite (Panonychus citri), apple spider mite (Panonychus ulmi), genus Oligonikus (Oligonychus spp.) Citrus mite (Aculops pelekassi), Citrus snail (Phyllocoptruta citri), Tomato snail (Aculops lycopersici), Scutellaris mite (Calacarus carinatus), Scutellariad mite (Acaphylla theavagrans), Nigella vulgaris (Acarus schlechtendali), Aceria diospyri, Aceria tosichella, Eriophyidae such as Shevtchenkella sp .; Eriophyidae; Polyphagotarsonemus latus E .. Red-handed spider mite (Tenuipalpidae), such as tick (Brevipalpus phoenicis); Teratididae (Tuckerelidae);・ Andersoni (Dermacentor and ersoni), Ixodes ovatus, Ixodes persulcatus, Ixodes ricinus, Black legged tick (Ixodes scapularis), American brown mite (Amblyomma americanum), Ambrium platinum rim maculatum), Boophilus microplus, Boophilus annulatus, Rhipicephalus sanguineus, and other ticks (Ixodidae); Acaridae (Acaridae), such as spiny pokeweed (Tyrophagus similis); Dermatophagoides farinae, Dermatophagoides pteronyssinus, etc .; Dermatophagiaceae (Pyroglyphidae); Red-handed mite (Chyletidae), such as the red-handed mite (Cheyletus moorei), and the dog's mite (Cheyletiella yasguri); (Demodicidae); Lepidoptera (Listrophoridae); Lepidoptera (Haplochthoniidae); Ornithnyssus bacoti, Ornithonyssus sylviarum, etc. Red mite family (Dermanyssidae) and the like; red pest of chiggers (Leptotrombidium akamushi) chiggers family, etc. (Trombiculidae).
　クモ目害虫（Araneae）：カバキコマチグモ（Cheiracanthium japonicum）等のコマチグモ科（Eutichuridae）；セアカゴケグモ（Latrodectus hasseltii）等のヒメグモ科（Theridiidae）の害虫。 Arachnid pests (Araneae): Pests of the family Eidichuridae, such as Chehiracanthium japonicum; and pests of the family Theridiidae, such as Latrodectus hasseltii.
　オビヤスデ目害虫（Polydesmida）：ヤケヤスデ（Oxidus gracilis）、アカヤスデ（Nedyopus tambanus）等のヤケヤスデ科（Paradoxosomatidae）の害虫。 Ovisyasdes pest (Polydesmida): Pests of the family Azalea (Paradoxosomatidae), such as yellow-faced snail (Oxidus gracilis), yellow-tailed snail (Nedyopus tambanus).
　等脚目害虫（Isopoda）：オカダンゴムシ（Armadillidium vulgare）等のオカダンゴムシ科（Armadillidiidae）の害虫。 Isopoda pests (Isopoda): pests of the Scutellariadidae family (Armadillidiidae), such as Armadillium vulgare.
　唇脚綱害虫（Chilopoda）：ゲジ（Thereuonema hilgendorfi）等のゲジ科（Scutigeridae）；トビズムカデ（Scolopendra subspinipes）等のオオムカデ科（Scolopendridae）；イッスンムカデ（Bothropolys rugosus）等のイッスンムカデ科（Ethopolidae）の害虫。 Lipopod pests (Chilopoda): Scutigeridae such as Thereuonema hilgendorfi; Scolopendra subspinipes et al. (Scolopendridae); .
　腹足綱害虫（Gastropoda）：チャコウラナメクジ（Limax marginatus）、キイロコウラナメクジ（Limax flavus）等のコウラナメクジ科（Limacidae）；ナメクジ（Meghimatium bilineatum）等のナメクジ科（Philomycidae）；スクミリンゴガイ（Pomacea canaliculata）等のリンゴガイ科（Ampullariidae）；ヒメモノアラガイ（Austropeplea ollula）等のモノアラガイ科（Lymnaeidae）の害虫。 Gastropoda pests (Gastropoda): Limax marginatus, Limax flavus, etc. (Limacidae); Ligacidae, such as slugs (Meghimatium bilineatum); Et al. (Ampullariidae); Pests of the family Monacaridae (Lymnaeidae) such as Aestropeplea ollula.
　線虫類（Nematoda）：イネシンガレセンチュウ(Aphelenchoides besseyi）等のアフェレンコイデス科（Aphelenchoididae）；ミナミネグサレセンチュウ(Pratylenchus coffeae）、Pratylenchus brachyurus、ムギネグサレセンチュウ(Pratylenchus neglectus）、ラドフォルス・シミリス(Radopholus similis)等のプラティレンクス科（Pratylenchidae）；ジャワネコブセンチュウ(Meloidogyne javanica）、サツマイモネコブセンチュウ（Meloidogyne incognita）、キタネコブセンチュウ(Meloidogyne hapla）、ダイズシストセンチュウ（Heterodera glycines）、ジャガイモシストセンチュウ(Globodera rostochiensis）、ジャガイモシロシストセンチュウ（Globodera pallida）等のヘテロデラ科（Heteroderidae）；Rotylenchulus reniformis等のホプロライムス科（Hoplolaimidae）；イチゴメセンチュウ（Nothotylenchus acris）、ジチレンクス・ジプサシ(Ditylenchus dipsaci）等のアングイナ科（Anguinidae）；チレンクルス・セミペネトランス(Tylenchulus semipenetrans）等のティレンクルス科（Tylenchulidae）；ブドウオオハリセン（Xiphinema index）等のロンギドルス科（Longidoridae）；トリコドルス科（Trichodoridae）；マツノザイセンチュウ（Bursaphelenchus xylophilus）等のパラシタアフェレンクス科(Parasitaphelenchidae)の線虫。 Nematoda (Nematoda): Aphelenchoides spp. (Aphelenchoides bessei) etc. Aphelenchoididae (Aphelenchoididae); similis) and the like (Pratylenchidae); Javanese Nematode (Meloidogyne javanica), Sweet potato Nematode (Meloidogyne incognita), Northern Nervosa (Meloidogyne hapla), Soybean cyst nematode (Heterodera glycines), White-tailed nematode (Globodera pallida) heterodera (Heteroderidae); Rotylenchulus reniformis et al. Hoplolaimidae; strawberry mesenchu (Nothotylenchus acris), dichilenx Anguinaceae family (Anguinidae) such as gypsy (Ditylenchus dipsaci); Tyrenculus family (Tylenchulidae) such as Tyrenculus seminetrans (Tylenchulus seminetrans); Nematodes of the Parasitaphelenchidae family, such as Bursaphelenchus xylophilus.
　防除対象としての有害節足動物において、有害昆虫および有害ダニ類は、殺虫・殺ダニ剤に薬剤感受性の低下した、または薬剤抵抗性の発達した昆虫およびダニ類であってもよい。ただし、薬剤感受性が大幅に低下した、または薬剤抵抗性が大幅に発達した場合は、その対象となる殺虫・殺ダニ剤以外の殺虫・殺ダニ剤成分を含む本発明組成物の使用が望ましい。 In the harmful arthropods to be controlled, the harmful insects and harmful mites may be insects and acarids that have reduced drug sensitivity to insecticidal and acaricidal agents, or have developed drug resistance. However, when the drug sensitivity is significantly reduced or drug resistance is significantly developed, it is desirable to use the composition of the present invention containing an insecticidal and acaricidal component other than the target insecticidal and acaricidal agent.
　本発明化合物は、昆虫媒介性ウイルス又は昆虫媒介性細菌による植物病害から植物を保護するためにも用いることができる。 The compounds of the present invention can also be used to protect plants from plant diseases caused by insect-borne viruses or insect-borne bacteria.
　かかる昆虫媒介性ウイルスとしては、例えば次のものが挙げられる。 Such insect-borne viruses include, for example, the following.
イネ矮化ウイルス（Rice tungro spherical virus）、イネツングロ桿菌状ウイルス（Rice tungro bacilliform virus）、イネグラッシースタントウイルス（Rice grassy stunt virus）、イネラギッドスタントウイルス（Rice ragged stunt virus）、イネ縞葉枯ウイルス（Rice stripe virus）、黒条萎縮ウイルス（Rice black streaked dwarf virus）、イネ南方黒すじ萎縮ウイルス（Southern rice black-streaked dwarf virus）、稲こぶ萎縮ウイルス（Rice gall dwarf virus）、イネ白葉病（Rice hoja blanca virus）、イネ黄葉ウイルス（Rice yellow stunt virus）、Rice yellow mottle virus、イネ萎縮ウイルス（Rice dwarf virus）、ムギ北地モザイクウイルス（Northern cereal mosaic virus）オオムギ黄萎ウイルス（Barley yellow dwarf virus）、オオムギ微斑ウイルス（Barley mild mosaic virus）、オオムギ黄萎PAVウイルス（Barley yellow dwarf virus-PAV）、ムギ類黄萎RPSウイルス（Cereal yellow dwarf virus-RPS）、コムギ黄葉ウイルス（Wheat yellow leaf virus）、Oat sterile dwarf virus、Wheat streak mosaic virus、
トウモロコシ萎縮モザイクウイルス（Maize dwarf mosaic virus）、Maize stripe virus、Maize chlorotic mottle virus、Maize chlorotic dwarf virus、Maize rayado fino virus、サトウキビモザイクウイルス（Sugarcane mosaic virus）、Fiji disease virus、Sugarcane yellow leaf virusダイズ微斑モザイクウイルス（Soybean mild mosaic virus）、ソテツえそ萎縮ウイルス（Cycas necrotic stunt）、ダイズ矮化ウイルス（Soybean dwarf virus）、レンゲ萎縮ウイルス（Milk vetch dwarf virus）、ダイズモザイクウイルス（Soybean mosaic virus）、アルファルファモザイクウイルス（Alfalfa mosaic virus）、インゲンマメ黄斑モザイクウイルス（Bean yellow mosaic virus）、インゲンマメモザイクウイルス（Bean common mosaic virus）、インゲンマメ南部モザイクウイルス（Southern bean mosaic virus）、ラッカセイ矮化ウイルス（Peanut stunt virus）、ソラマメウイルトウイルス１（Broad bean wilt virus 1）、ソラマメウイルトウイルス２（Broad bean wilt virus 2）、ソラマメえそモザイクウイルス（Broad bean necrosis virus）、ソラマメ葉脈黄化ウイルス（Broad bean yellow vein virus）、クローバ葉脈黄化ウイルス（Clover yellow vein virus）、ラッカセイ斑紋ウイルス（Peanut mottle virus）、タバコ条斑ウイルス（Tobacco streak virus）、Bean pod mottle virus、Cowpea chlorotic mottle virus、Mung bean yellow mosaic virus、Soybean crinkle leaf virus、トマト退緑ウイルス（Tomato chlorosis virus）、トマト黄化えそウイルス（Tomato spotted wilt virus）、トマト黄化葉巻ウイルス（Tomato yellow leaf curl virus）、トマトアスパーミィウイルス（Tomato aspermy virus）、トマトインフェクシャスクロロシスウイルス（Tomato infectious chlorosis virus）、ジャガイモ葉巻ウイルス（Potato leafroll virus）、ジャガイモＹウイルス（Potato virus Y）、メロン黄化えそウイルス（Melon yellow spot virus）、メロンえそ斑点ウイルス（Melon necrotic spot virus）、スイカモザイクウイルス（Watermelon mosaic virus）、キュウリモザイクウイルス（Cucumber mosaic virus）、ズッキーニ黄斑モザイクウイルス（Zucchini yellow mosaic virus）、カブモザイクウイルス（Turnip mosaic virus）、カブ黄化モザイクウイルス（Turnip yellow mosaic virus）、カリフラワーモザイクウイルス（Cauliflower mosaic virus）、レタスモザイクウイルス（Lettuce mosaic virus）、セルリーモザイクウイルス（Celery mosaic virus）、ビートモザイクウイルス（Beet mosaic virus）、ウリ類退緑黄化ウイルス（Cucurbit chlorotic yellows virus）、トウガラシ退緑ウイルス（Capsicum chlorosis virus）、ビートシュードイエロースウイルス（Beet pseudo yellows virus）、リーキ黄色条斑ウイルス（Leak yellow stripe virus）、タマネギ萎縮ウイルス（Onion yellow dwarf virus）、サツマイモ斑紋モザイク病（Sweet potato feathery mottle virus）、サツマイモ縮葉モザイク病（Sweet potato shukuyo mosaic virus）、イチゴ斑紋ウイルス（Strawberry mottle virus）、イチゴマイルドイエローエッジウイルス（Strawberry mild yellow edge virus）、イチゴシュードマイルドイエローエッジウイルス（Strawberry pseudo mild yellow edge virus）、イチゴクリンクルウイルス（Strawberry crinkle virus）、イチゴべインバンディングウイルス（Strawberry vein banding virus）、ウメ輪紋ウイルス（plum pox virus）、キク茎えそウイルス（Chrysanthemum stem necrosis virus）、インパチェンスえそ斑点ウイルス（Impatiens necrotic spot virus）、アイリス黄斑ウイルス（Iris yellow spot virus）、ユリ微斑ウイルス（Lily mottle cirus）、ユリ潜在ウイルス（Lilly symptomless virus）、チューリップモザイクウイルス（Tulip mosaic virus）等。 Rice hatching virus (Rice tungro spherical virus), rice tungro bacillus virus (Rice tungro bacilliform virus), rice grassy stunt virus (Rice grassy stunt virus), rice ragged stunt virus (Rice ragged stunt virus), rice streak dead virus ( Rice stripe virus), Rice black streaked dwarf virus, Rice southern black streaked dwarf virus, Rice gall dwarf virus, Rice hoja disease (Rice hoja) blanca virus), rice yellow leaf virus (Rice yellow stunt virus), rice yellow mottle virus, rice dwarf virus, wheat cereals northern virus (Northern cereal mosaic virus) barley yellow dwarf virus (Barley yellow dwarf virus), Barley mild mosaic virus, Barley yellow dwarf virus (Barley yellow dwarf virus-PAV), Ruiki萎 RPS virus (Cereal yellow dwarf virus-RPS), wheat yellow leaves virus (Wheat yellow leaf virus), Oat sterile dwarf virus, Wheat streak mosaic virus,
Maize dwarf mosaic virus (Maize dwarf mosaic virus), Maize stripe virus, Maize chlorotic mottle virus, Maize chlorotic dwarf virus, Maize rayado fino virus, Sugar cane mosaic virus (Sugarcane mosaic virus), Fiji disease virus, Sugarcane yellow leaf virus Mosaic virus (Soybean mild mosaic virus), Cyet necrotic virus (Cycas necrotic stunt), Soybean dwarf virus (Soybean dwarf virus), Japanese dander virus (Milk vetch dwarf virus), Soybean mosaic virus (Soybean mosaic virus), alfalfa Mosaic virus (Alfalfa mosaic virus), kidney bean macula yellow spot virus (Bean yellow mosaic virus), kidney bean mosaic virus (Bean common mosaic virus), kidney bean southern mosaic virus (Southern bean mosaic virus), peanut blossom virus (Peanut stunt virus), Sorama Wilt virus 1 (Broad bean wilt virus 1), Broad bean wilt virus 2 (Broad bean wilt virus 2), Broad bean necrosis virus (Broad bean necrosis virus), Broad bean yellow vein virus (Broad bean yellow vein virus), Clover yellow vein virus (Clover yellow vein virus), Peanut mottle virus, Tobacco streak virus, Bean pod mottle virus, Cowpea chlorotic mottle virus, Mung bean yellow mosaic virus, Soybean crinkle leaf virus, tomato chlorosis virus (Tomato chlorosis virus), tomato spotted wilt virus, tomato yellow leaf curl virus (Tomato yellow leaf curl virus), tomato aspermy virus (Tomato aspermy virus), tomato infe Tokuso chlorosis virus (Tomato infectious chlorosis virus), potato leaf curl virus (Potato leafrol) virus, Potato virus Y (Potato virus Y), Melon yellow spot virus (Melon yellow spot virus), Melon necrotic spot virus (Melon necrotic spot virus), Watermelon mosaic virus (Watermelon mosaic virus), Cucumber mosaic virus (Cucumber mosaic virus), Zucchini yellow mosaic virus (Zucchini yellow mosaic virus), turnip mosaic virus (Turnip mosaic virus), turnip yellow mosaic virus (Turnip yellow mosaic virus), cauliflower mosaic virus (Cauliflower mosaic virus), lettuce mosaic virus (Lettuce mosaic virus), celery mosaic virus (Celery mosaic virus), beet mosaic virus (Beet mosaic virus), Cucurbita chlorotic yellows virus (Cucurbit chlorotic yellows virus), red pepper virulence virus (Capsicum chlorine virus), beet-sued Yellows virus (Beet pseudo do yellows virus), Leak yellow stripe virus, Onion yellow dwarf virus, Sweet potato feathery mottle virus, Sweet potato shukuyo mosaic virus ), Strawberry mottle virus, strawberry mild yellow edge virus, strawberry pseudo mild yellow edge virus, strawberry crinkle virus, strawberry beak Inbanding virus (Strawberry vein banding virus), plum bloom virus (plum pox virus), chrysanthemum stem necrosis virus (Chrysanthemum stem necrosis virus), impatiens necrotic spot virus (Impatiens necrotic spot virus), iris macular virus (Iris yellow) spot virus), lily Mottle virus (Lily mottle cirus), lily latent virus (Lilly symptomless virus), tulip mosaic virus (Tulip mosaic virus) and the like.
　昆虫媒介性細菌としては、例えば次のものが挙げられる。 Examples of insect-borne bacteria include the following.
　イネ黄萎病ファイトプラズマ（Candidatus Phytoplasma oryzae）、Candidatus Phytoplasma asteris、Maize bushy stunt phytoplasma、カンキツグリーニング病菌アジア型（Candidatus Liberbacter asiaticus）、カンキツグリーニング病菌アフリカ型（Candidatus Liberbacter africanus）、カンキツグリーニング病菌アメリカ型（Candidatus Liberbacter americanus）等。 Rice yellow dwarf phytoplasma (Candidatus Phytoplasma oryzae), Candidatus Phytoplasma asteris, Maize bushy stunt phytoplasma, citrus greening fungus Asian type (Candidatus Liberbacter asiaticus), citrus greening fungus African type (Candidatus Liberbacter aflicanus), Type (Candidatus Liberbacter americanus) etc.
　本発明の有害節足動物防除組成物は、本発明化合物又は組成物Ａと不活性担体とを含有する（以下、「本発明組成物」と記す）。本発明組成物は、通常、本発明化合物又は組成物Ａと、固体担体、液体担体、ガス状担体等の不活性担体とを混合し、必要に応じて界面活性剤、その他の製剤用補助剤を添加して、乳剤、油剤、粉剤、粒剤、水和剤、顆粒水和剤、フロアブル剤、ドライフロアブル剤、マイクロカプセル剤、エアゾール剤、毒餌剤、樹脂製剤、シャンプー剤、ペースト状製剤、泡沫剤、炭酸ガス製剤、錠剤等に製剤化されている。これらの製剤は蚊取り線香、電気蚊取りマット、液体蚊取り製剤、燻煙剤、燻蒸剤、シート製剤、スポットオン剤、経口処理剤に加工されて、使用されることもある。本発明組成物は、本発明化合物を通常０．０１～９５重量％含有する。 The noxious arthropod controlling composition of the present invention contains the present compound or composition A and an inert carrier (hereinafter referred to as "the present composition"). The composition of the present invention generally mixes the compound or composition A of the present invention with an inert carrier such as a solid carrier, liquid carrier, gaseous carrier, and, if necessary, a surfactant and other adjuvants for formulation. Add emulsion, oil, powder, granules, wettable, flowable, flowable, dry flowable, microcapsule, aerosol, poison bait, resin formulation, shampoo, pasty formulation, It is formulated into foams, carbon dioxide preparations, tablets and the like. These preparations may be used as processed into mosquito coil, electric mosquito mat, liquid mosquito formula, fuming agent, fumigant, sheet preparation, spot-on agent, oral treatment agent. The composition of the present invention usually contains 0.01 to 95% by weight of the compound of the present invention.
　製剤化の際に用いられる固体担体としては、例えば粘土類（カオリンクレー、珪藻土、ベントナイト、フバサミクレー、酸性白土等）、乾式シリカ、湿式シリカ、タルク、セラミック、その他の無機鉱物（セリサイト、石英、硫黄、活性炭、炭酸カルシウム等）、化学肥料（硫安、燐安、硝安、尿素、塩安等）等の微粉末及び粒状物等、並びに合成樹脂（ポリプロピレン、ポリアクリロニトリル、ポリメタクリル酸メチル、ポリエチレンテレフタレート等のポリエステル樹脂、ナイロン－６、ナイロン－１１、ナイロン－６６等のナイロン樹脂、ポリアミド樹脂、ポリ塩化ビニル、ポリ塩化ビニリデン、塩化ビニル－プロピレン共重合体等）が挙げられる。 Examples of solid carriers used in formulation include clays (kaolin clay, diatomaceous earth, bentonite, fuvasami clay, acid clay etc.), dry silica, wet silica, talc, ceramic, and other inorganic minerals (sericite, quartz, Fine powders and particles such as sulfur, activated carbon, calcium carbonate etc., chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, sodium chloride etc.) and synthetic resins (polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate) And polyester resins, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymers, and the like.
　液体担体としては、例えば水、アルコール類（メタノール、エタノール、イソプロピルアルコール、ブタノール、ヘキサノール、ベンジルアルコール、エチレングリコール、プロピレングリコール、フェノキシエタノール等）、ケトン類（アセトン、メチルエチルケトン、シクロヘキサノン等）、芳香族炭化水素類（トルエン、キシレン、エチルベンゼン、ドデシルベンゼン、フェニルキシリルエタン、メチルナフタレン等）、脂肪族炭化水素類（ヘキサン、シクロヘキサン、灯油、軽油等）、エステル類（酢酸エチル、酢酸ブチル、ミリスチン酸イソプロピル、オレイン酸エチル、アジピン酸ジイソプロピル、アジピン酸ジイソブチル、プロピレングリコールモノメチルエーテルアセテート等）、ニトリル類（アセトニトリル、イソブチロニトリル等）、エーテル類（ジイソプロピルエーテル、１，４－ジオキサン、１，２－ジメトキシエタン、ジエチレングリコールジメチルエーテル、ジエチレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテル、ジプロピレングリコールモノメチルエーテル、３－メトキシ－３－メチル－１－ブタノール等）、アミド類（ＤＭＦ、Ｎ，Ｎ－ジメチルアセトアミド等）、スルホキシド類（ジメチルスルホキシド等）、炭酸プロピレン及び植物油（大豆油、綿実油等）が挙げられる。 Examples of liquid carriers include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone etc.), aromatic hydrocarbons (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc., nitriles (acetonitrile, isobutyric acid) Nitriles etc., Ethers (diisopropyl ether, 1,4-dioxane, 1,2-dimethoxyethane, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1 -Butanol etc., amides (DMF, N, N-dimethyl acetamide etc.), sulfoxides (dimethyl sulfoxide etc.), propylene carbonate and vegetable oil (soybean oil, cottonseed oil etc.).
　ガス状担体としては、例えばフルオロカーボン、ブタンガス、ＬＰＧ（液化石油ガス）、ジメチルエーテル及び炭酸ガスが挙げられる。 Gaseous carriers include, for example, fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide gas.
　界面活性剤としては、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アリールエーテル、ポリエチレングリコール脂肪酸エステル等の非イオン界面活性剤、及びアルキルスルホン酸塩、アルキルベンゼンスルホン酸塩、アルキル硫酸塩等の陰イオン界面活性剤が挙げられる。 Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactants may be mentioned.
　その他の製剤用補助剤としては、固着剤、分散剤、着色剤及び安定剤等、具体的には例えばカゼイン、ゼラチン、糖類（でんぷん、アラビアガム、セルロース誘導体、アルギン酸等）、リグニン誘導体、ベントナイト、合成水溶性高分子（ポリビニルアルコール、ポリビニルピロリドン、ポリアクリル酸類等）、酸性リン酸イソプロピル、２，６－ジ－ｔｅｒｔ－ブチル－４－メチルフェノール、ＢＨＡ（２－ｔｅｒｔ－ブチル－４－メトキシフェノールと３－ｔｅｒｔ－ブチル－４－メトキシフェノールとの混合物）が挙げられる。 As other pharmaceutical adjuvants, fixing agents, dispersing agents, coloring agents, stabilizers and the like, specifically, for example, casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, 2,6-di-tert-butyl-4-methylphenol, BHA (2-tert-butyl-4-methoxyphenol) And a mixture of 3-tert-butyl-4-methoxyphenol).
　樹脂製剤の基材としては、例えば塩化ビニル系重合体、ポリウレタン等を挙げることができ、これらの基材には必要によりフタル酸エステル類（フタル酸ジメチル、フタル酸ジオクチル等）、アジピン酸エステル類、ステアリン酸等の可塑剤が添加されていてもよい。樹脂製剤は該基材中に化合物を通常の混練装置を用いて混練した後、射出成型、押出成型、プレス成型等により成型することにより得られ、必要により更に成型、裁断等の工程を経て、板状、フィルム状、テープ状、網状、ひも状等の樹脂製剤に加工できる。これらの樹脂製剤は、例えば動物用首輪、動物用イヤータッグ、シート製剤、誘引ひも、園芸用支柱として加工される。
　毒餌剤の基材としては、例えば穀物粉、植物油、糖、結晶セルロース等が挙げられ、更に必要に応じて、ジブチルヒドロキシトルエン、ノルジヒドログアイアレチン酸等の酸化防止剤、デヒドロ酢酸等の保存料、トウガラシ末等の子供やペットによる誤食防止剤、チーズ香料、タマネギ香料ピーナッツオイル等の害虫誘引性香料等が添加される。 Examples of the base material of the resin preparation include vinyl chloride polymers, polyurethane and the like, and phthalate esters (dimethyl phthalate, dioctyl phthalate, etc.), adipates, etc. may be used as necessary for these bases. And a plasticizer such as stearic acid may be added. The resin formulation is obtained by kneading the compound in the base using a common kneading apparatus, and then molding by injection molding, extrusion molding, press molding and the like, and if necessary, through further steps such as molding and cutting, It can be processed into resin preparations such as plate-like, film-like, tape-like, net-like and string-like. These resin preparations are processed, for example, as animal collars, animal ear tags, sheet preparations, drawstrings, horticultural posts.
Examples of the substrate for poison bait include cereal flour, vegetable oil, sugar, crystalline cellulose and the like, and further, if necessary, preservation of antioxidant such as dibutyl hydroxytoluene, nordihydroguaiaretic acid, dehydroacetic acid etc. , An anti-mistake agent for children and pets such as capsicum powder, a cheese flavor, an onion flavor and a pest-inducing flavor such as peanut oil are added.
　本発明の有害節足動物の防除方法は、本発明組成物の有効量を有害節足動物に直接、及び／又は、有害節足動物の生息場所（植物、土壌、家屋内、動物等）に施用することにより行われる。また、種子に処理することもできる。 In the method of controlling an arthropod pest of the present invention, an effective amount of the composition of the present invention is directly applied to the arthropod pest and / or to a habitat of the arthropod pest (plant, soil, house, animal, etc.) It is carried out by applying. It can also be treated on seeds.
　本発明において、植物としては、植物全体、茎葉、花、穂、果実、樹幹、枝、樹冠、種子、栄養生殖器官及び苗が挙げられる。 In the present invention, plants include whole plants, stems and leaves, flowers, ears, fruits, trunks, branches, crowns, seeds, vegetative organs and seedlings.
　栄養生殖器官とは、植物の根、茎、葉等のうち、その部位を本体から切り離して土壌に設置した場合に、成長する能力を持つものを意味する。栄養生殖器官としては、例えば、塊根（tuberous root）、横走根（creeping root）、鱗茎（bulb）、球茎（corm又はsolid bulb）、塊茎（tuber）、根茎（rhizome）、匍匐枝（stolon）、担根体（rhizophore）、茎断片（cane cuttings）、むかご（propagule）及びつる（vine cutting）が挙げられる。なお、匍匐枝は、ランナー（runner）と呼ばれることもあり、むかごは、珠芽とも呼ばれ、肉芽（broad bud）、鱗芽（bulbil）に分けられる。つるとは、サツマイモやヤマノイモ等の苗条（葉及び茎の総称、shoot）を意味する。鱗茎、球茎、塊茎、根茎、茎断片、担根体又は塊根を総称して、球根とも呼ばれている。例えば、イモの栽培は塊茎を土壌に植え付けることで始めるが、用いられる塊茎は一般に種芋と呼ばれる。 The vegetative organ means the plant roots, stems, leaves, etc. that have the ability to grow when the site is separated from the main body and installed in the soil. As the vegetative reproductive organs, for example, tuberous root, creeping root, bulb, corm or solid bulb, tuber, tuber, rhizome, stolon Rhizophores, cane cuttings, propagule and vine cutting. In addition, a toothpick is also called a runner (runner), and a basket is also called a sprout and is divided into a broad bud and a bulbil (bulbil). "Vine" means shoots such as sweet potato and yam (collectively referred to as leaves and stems, shoot). The bulbs, corms, tubers, rhizomes, stem fragments, rhizomes or tuberous roots are collectively referred to as bulbs. For example, cultivation of potato starts by planting tubers in the soil, but the tubers used are generally called seed potatoes.
　本発明組成物の施用方法としては、例えば、茎葉処理、土壌処理、根部処理、シャワー処理、燻煙処理、水面処理及び種子処理が挙げられる。 Examples of the method of applying the composition of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, smoke treatment, water surface treatment and seed treatment.
　本発明組成物の有効量を、植物又は植物を栽培する土壌に施用する方法としては、例えば、植物へ本発明化合物又は本発明組成物の有効量を施用する方法、種子消毒や種子浸漬、種子コート等の種子又は栄養生殖器官へ本発明化合物又は本発明組成物の有効量を施用する方法、及び植物を植えつける前又は植えつけた後の土壌に本発明化合物又は本発明組成物の有効量を施用する方法が挙げられる。 As a method of applying an effective amount of the composition of the present invention to a plant or a soil for cultivating a plant, for example, a method of applying an effective amount of the compound of the present invention or the composition of the present invention to plants A method of applying an effective amount of the compound of the present invention or the composition of the present invention to seeds or vegetative reproductive organs such as coats, and an effective amount of the compound of the present invention or the composition of the present invention in the soil before planting or after planting Methods of applying
　本発明組成物の有効量を、植物を植えつける前又は植えつけた後の土壌に施用することによる有害節足動物を防除する方法は、例えば、有害節足動物による摂食等の被害から保護しようとする作物の根圏に本発明組成物の有効量を施用して有害節足動物を直接防除する方法、及び根部等から植物体内部に本発明組成物の有効量を浸透移行させて、植物を摂食する有害節足動物を防除する方法が挙げられる。より具体的には、例えば、植穴処理（植穴散布、植穴処理土壌混和）、株元処理（株元散布、株元土壌混和、株元灌注、育苗期後半株元処理）、植溝処理（植溝散布、植溝土壌混和）、作条処理（作条散布、作条土壌混和、生育期作条散布）、播種時作条処理（播種時作条散布、播種時作条土壌混和）、全面処理（全面土壌散布、全面土壌混和）、側条処理、水面処理（水面施用、湛水後水面施用）、その他土壌散布処理（生育期粒剤葉面散布、樹冠下または主幹周辺散布、土壌表面散布、土壌表面混和、播穴散布、畦部地表面散布、株間散布）、その他灌注処理（土壌灌注、育苗期灌注、薬液注入処理、地際部灌注、薬液ドリップイリゲーション、ケミゲーション）、育苗箱処理（育苗箱散布、育苗箱灌注、育苗箱薬液湛水）、育苗トレイ処理（育苗トレイ散布、育苗トレイ灌注、育苗トレイ薬液湛水）、苗床処理（苗床散布、苗床灌注、水苗代苗床散布、苗浸漬）、床土混和処理（床土混和、播種前床土混和、播種時覆土前散布、播種時覆土後散布、覆土混和）、及びその他処理（培土混和、鋤き込み、表土混和、雨落ち部土壌混和、植位置処理、粒剤花房散布、ペースト肥料混和）が挙げられる。 A method for controlling harmful arthropods by applying an effective amount of the composition of the present invention to the soil before planting or after planting is, for example, protection from damage such as feeding by harmful arthropods A method of controlling an arthropod pest directly by applying an effective amount of the composition of the present invention to the root zone of a desired crop, and permeating the effective amount of the composition of the present invention into the plant from roots and the like, Methods for controlling harmful arthropods that feed on plants are mentioned. More specifically, for example, planting hole processing (planting hole spraying, planting hole treated soil mixing), stock source treatment (stock source spraying, stock source soil mixing, stock source irrigation, rearing seedling period second half stock source processing), weeding groove Treatment (plant groove dispersion, mixture groove soil mixing), line processing (line distribution, line soil mixing, growth period line dispersion), sowing processing at the time of sowing (line dispersion at the time of sowing, soil mixing at the time of sowing) ), All-surface treatment (all-surface soil spraying, all-surface soil mixing), side treatment, water surface treatment (water surface application, spring application after water application, water surface application), other soil dispersion treatment (growing season foliage surface dispersion, under crown or around main trunk) Spraying the soil surface, mixing the soil surface, spraying the seed hole, spraying the surface of the buttocks, spraying between the plants, etc., other irrigation treatment (soil irrigation, nursery irrigation, chemical injection treatment, irrigation at the ground, chemical drip irrigation, chemistry) , Seedling box processing (seedling box dispersion, seedling box irrigation, seedling box medical solution spring), seedling tray Management (seedling tray spreading, seedling tray irrigation, seedling tray medical solution watering), nursery treatment (seedling spreading, seedling irrigation, seedling seedling spreading, seedling soaking), mixed bed soil treatment (mixed bed soil, mixed bed soil before seeding, Before sowing, soaking at the time of sowing, soaking at the time of sowing, soaking in soil), and other treatments (mixing in soil, mixing in, soaking, mixing in soil, mixing in wet soil, planting location treatment, spraying of flower bunches, mix in paste fertilizer) It can be mentioned.
　本発明組成物を農業分野の有害節足動物防除に用いる場合、その施用量は、１０,０００ｍ2あたりの本発明化合物量で通常１～１０,０００ｇである。種子又は栄養生殖器官に処理する場合は、本発明化合物の有効量は、種子又は栄養生殖器官１ｋｇあたり、通常０．００１～１００ｇ、好ましくは０．０２～２０ｇである。組成物Ａの有効量は、種子又は栄養生殖器官１ｋｇあたり、通常０．００１～１００ｇ、好ましくは０．０１～５０ｇである。本発明組成物が乳剤、水和剤、フロアブル剤等に製剤化されている場合は、通常、有効成分濃度が０．０１～１０,０００ｐｐｍとなるように水で希釈して施用し、粒剤、粉剤等は、通常、そのまま施用する。 When the composition of the present invention is used for controlling harmful arthropods in the agricultural field, the application rate is usually 1 to 10,000 g of the present compound per 10,000 m 2 . When treating a seed or vegetative organ, the effective amount of the compound of the present invention is usually 0.001 to 100 g, preferably 0.02 to 20 g, per kg of the seed or vegetative organ. The effective amount of the composition A is usually 0.001 to 100 g, preferably 0.01 to 50 g, per kg of the seed or vegetative organ. When the composition of the present invention is formulated into an emulsion, a wettable powder, a flowable, etc., it is usually diluted with water so as to have an active ingredient concentration of 0.01 to 10,000 ppm, and applied. Powders, etc. are usually applied as they are.
　これらの製剤や製剤の水希釈液は、有害節足動物又は有害節足動物から保護すべき作物等の植物に直接散布処理してもよく、また耕作地の土壌に生息する有害節足動物を防除するために、該土壌に処理してもよい。 These formulations and their dilutions may be sprayed directly onto plants, such as harmful arthropods or crops to be protected from harmful arthropods, and harmful arthropods that inhabit the soil of cultivated land The soil may be treated to control.
　また、シート状やひも状に加工した樹脂製剤を作物に巻き付ける、作物近傍に張り渡す、株元土壌に敷く等の方法により処理することもできる。 In addition, the resin preparation processed into a sheet or string can be treated by a method such as wrapping around a crop, spreading it in the vicinity of a crop, spreading it on stock soil, or the like.
　本発明組成物を家屋内に生息する有害節足動物の防除に用いる場合、その施用量は、面上に処理する場合は処理面積１ｍ2あたりの本発明化合物量で、通常、０．０１～１,０００ｍｇであり、空間に処理する場合は処理空間１ｍ3あたりの本発明化合物量で、通常、０．０１～５００ｍｇである。本発明組成物が乳剤、水和剤、フロアブル剤等に製剤化されている場合は、通常有効成分濃度が０．１～１０,０００ｐｐｍとなるように水で希釈して施用し、油剤、エアゾール剤、燻煙剤、毒餌剤等はそのまま施用する。 When the composition of the present invention is used for controlling harmful arthropods that live in a house, the amount of the compound applied is usually 0.01 to 10% of the compound of the present invention per 1 m 2 of treated area when treated on a surface. The amount of the compound of the present invention per 1 m 3 of treatment space is usually 0.01 to 500 mg when treated in a space. When the composition of the present invention is formulated into an emulsion, a wettable powder, a flowable and the like, it is usually diluted with water so as to have an active ingredient concentration of 0.1 to 10,000 ppm, and applied. Apply the agent, fuming agent, poison bait etc. as it is.
　本発明組成物をウシ、ウマ、ブタ、ヒツジ、ヤギ、ニワトリ等の家畜、イヌ、ネコ、ラット、マウス等の小動物の外部寄生虫防除に用いる場合は、獣医学的に公知の方法で動物に使用することができる。具体的な使用方法としては、全身抑制を目的にする場合には、例えば錠剤、飼料混入、坐薬、注射（筋肉内、皮下、静脈内、腹腔内等）により投与され、非全身的抑制を目的とする場合には、例えば油剤若しくは水性液剤を噴霧する、ポアオン処理若しくはスポットオン処理を行う、シャンプー製剤で動物を洗う又は樹脂製剤を首輪や耳札にして動物に付ける等の方法により用いられる。動物に投与する場合の本発明化合物の量は、通常動物の体重１ｋｇに対して、０．１～１,０００ｍｇの範囲である。 When the composition of the present invention is used to control ectoparasites of small animals such as cattle, horses, pigs, sheep, goats, chickens, etc., dogs, cats, rats, mice, etc. It can be used. As a specific method of use, for the purpose of systemic suppression, for example, it is administered by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal etc.) and is intended for non-systemic suppression. In this case, for example, oil or aqueous solution is sprayed, pour-on treatment or spot-on treatment is performed, the animal is washed with a shampoo preparation, or the resin preparation is used as a collar or ear tag and attached to the animal. The amount of the compound of the present invention when administered to animals is usually in the range of 0.1 to 1,000 mg per kg of animal weight.
　また、本発明組成物は、畑、水田、芝生、果樹園等の農耕地における有害節足動物の防除剤として使用することができる。本発明組成物は、以下に挙げられる植物等を栽培する農耕地等において、当該農耕地等の有害節足動物を防除することができる。 In addition, the composition of the present invention can be used as a control agent for harmful arthropods in agricultural land such as fields, paddy fields, lawns, orchards and the like. The composition of the present invention can control harmful arthropods such as the agricultural land in the agricultural land where the plants listed below are cultivated.
　農作物；トウモロコシ、イネ、コムギ、オオムギ、ライムギ、エンバク、ソルガム、ワタ、ダイズ、ピーナッツ、ソバ、テンサイ、ナタネ、ヒマワリ、サトウキビ、タバコ等、
　野菜；ナス科野菜（ナス、トマト、ピーマン、トウガラシ、ジャガイモ等）、ウリ科野菜（キュウリ、カボチャ、ズッキーニ、スイカ、メロン等）、アブラナ科野菜（ダイコン、カブ、セイヨウワサビ、コ－ルラビ、ハクサイ、キャベツ、カラシナ、ブロッコリー、カリフラワー等）、キク科野菜（ゴボウ、シュンギク、アーティチョーク、レタス等）、ユリ科野菜（ネギ、タマネギ、ニンニク、アスパラガス）、セリ科野菜（ニンジン、パセリ、セロリ、アメリカボウフウ等）、アカザ科野菜（ホウレンソウ、フダンソウ等）、シソ科野菜（シソ、ミント、バジル等）、イチゴ、サツマイモ、ヤマノイモ、サトイモ等、花卉、観葉植物、
　果樹；仁果類（リンゴ、セイヨウナシ、ニホンナシ、カリン、マルメロ等）、核果類（モモ、スモモ、ネクタリン、ウメ、オウトウ、アンズ、プルーン等）、カンキツ類（ウンシュウミカン、オレンジ、レモン、ライム、グレープフルーツ等）、堅果類（クリ、クルミ、ハシバミ、アーモンド、ピスタチオ、カシューナッツ、マカダミアナッツ等）、液果類（ブルーベリー、クランベリー、ブラックベリー、ラズベリー等）、ブドウ、カキ、オリーブ、ビワ、バナナ、コーヒー、ナツメヤシ、ココヤシ等、
　果樹以外の樹；チャ、クワ、花木、街路樹（トネリコ、カバノキ、ハナミズキ、ユーカリ、イチョウ、ライラック、カエデ、カシ、ポプラ、ハナズオウ、フウ、プラタナス、ケヤキ、クロベ、モミノキ、ツガ、ネズ、マツ、トウヒ、イチイ）等。 Agricultural products: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugar cane, tobacco etc.
Vegetables: Solanaceous vegetables (eggplant, tomato, pepper, pepper, potato), Cucurbita vegetables (eg, cucumber, pumpkin, zucchini, watermelon, melon), Brassica vegetables (Japanese radish, turnip, horseradish, horse mackerel, Chinese cabbage) , Cabbage, mustard, broccoli, cauliflower etc), Asteraceae vegetables (burdock, shung chrysanthemum, artichoke, lettuce etc), Liliaceae vegetables (Leeks, onions, garlic, asparagus), Seriaceae vegetables (carrot, parsley, celery, American Bofffew, etc.), vulgare family vegetables (spinach, swiss chard etc.), sage family vegetables (sesame, mint, basil etc.), strawberries, sweet potato, yamanoimo, taro etc., flower buds, houseplants,
Fruits; Fruits (apples, pears, Japanese pears, cullins, quince etc.), Core fruits (momo, plums, nectarines, jujubes, apricots, prunes etc.), citrus fruits (palms, oranges, lemons, limes, grapefruits) Etc), nuts (nuts, walnuts, hazelnuts, almonds, pistachios, cashews, macadamias etc), berries (blueberries, cranberries, blackberries, raspberries etc), grapes, oysters, olives, loquats, bananas, coffee, etc. Date palm, coconut palm, etc.
Trees other than fruit trees; tea, mulberry, flowering trees, street trees (astera, birch, dogwood, eucalyptus, eucalyptus, ginkgo, lilac, maple, oak, poplar, persimmon, perennial, fusarium, plananas, persimmon, perianthus, birch, fir tree, tsuga, nezu Spruce, yew) etc.
　上記植物は、自然交配で作出しうる植物、突然変異により発生しうる植物、F1ハイブリッド植物、及び遺伝子組換え作物も含まれる。遺伝子組換え作物としては、例えばイソキサフルトール等のHPPD（４－ヒドロキシフェニルピルビン酸ジオキシゲナーゼ酵素）阻害剤、イマゼタピル、チフェンスルフロンメチル等のALS（アセト乳酸合成酵素）阻害剤、EPSP（５－エノールピルビルシキミ酸－３－リン酸合成酵素）阻害剤、グルタミン合成酵素阻害剤、PPO（プロトポルフィリノーゲン酸化酵素）阻害剤、ブロモキシニル、又はジカンバ等の除草剤に対する耐性が付与された植物；バチルス・チューリンゲンシス（Bacillus thuringiensis）などのバチルス属で知られている選択的毒素等を合成することが可能となった植物；有害昆虫由来の内在性遺伝子に部分的に一致する遺伝子断片等を合成し、標的有害昆虫体内でジーンサイレンシング（RNAi；RNA interference）を誘導することにより特異的な殺虫活性を付与することができる植物が挙げられる。 The above-mentioned plants also include plants which can be produced by natural mating, plants which can be generated by mutation, F1 hybrid plants and genetically modified crops. Examples of genetically modified crops include HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutole, ALS (acetolactate synthetase) inhibitors such as imazethapyr and thifensulfuron methyl, EPSP (5 -Plants with resistance to herbicides such as -enolpyruvyl shikimate-3-phosphate synthetase inhibitor, glutamine synthetase inhibitor, PPO (protoporphyrinogen oxidase) inhibitor, bromoxynil, or dicamba A plant capable of synthesizing selective toxins and the like known in Bacillus genera such as Bacillus thuringiensis; gene fragments and the like partially corresponding to endogenous genes derived from harmful insects; Synthesized and specifically induced by inducing gene silencing (RNAi; RNA interference) in the target harmful insect body. Included are plants capable of conferring different insecticidal activities.
　上記植物は、一般的に栽培される品種であれば特に限定はない。 The above-mentioned plant is not particularly limited as long as it is a commonly grown variety.
　以下、本発明を製造例、参考製造例、製剤例及び試験例等によりさらに詳しく説明するが、本発明はこれらの例のみに限定されるものではない。
　まず、本発明化合物の製造例を示す。 Hereinafter, the present invention will be described in more detail by Production Examples, Reference Production Examples, Formulation Examples, Test Examples and the like, but the present invention is not limited to these examples.
First, production examples of the compound of the present invention will be shown.
参考製造例１
　３，５－ジフルオロピリジン－２－カルボン酸５０ｇ、ＤＭＦ１ｍＬ及びトルエン２５０ｍＬの混合物に窒素雰囲気下１００℃で塩化チオニル３８．９ｍＬを加え、２時間撹拌した。得られた混合物を減圧下で濃縮し、残渣に２８％アンモニア水１００ｍＬ及びトルエン５０ｍＬの混合物を加え、室温で１時間撹拌した。得られた固体をろ取し水で洗浄した後、乾燥し、次式で示される中間体１を３８．０ｇ得た。
Figure JPOXMLDOC01-appb-C000041
 中間体１：1H-NMR (CDCl3) δ: 8.32 (1H, s), 7.51 (1H, br s), 7.35 (1H, dd), 5.77 (1H, br s). Reference Production Example 1
To a mixture of 50 g of 3,5-difluoropyridine-2-carboxylic acid, 1 mL of DMF and 250 mL of toluene was added 38.9 mL of thionyl chloride at 100 ° C. under a nitrogen atmosphere, and stirred for 2 hours. The resulting mixture was concentrated under reduced pressure, a mixture of 100 mL of 28% aqueous ammonia and 50 mL of toluene was added to the residue, and stirred at room temperature for 1 hour. The obtained solid was collected by filtration, washed with water, and dried to give 38.0 g of Intermediate 1 represented by the following formula.
Figure JPOXMLDOC01-appb-C000041
 Intermediate 1: 1 H-NMR (CDCl 3 ) δ: 8.32 (1 H, s), 7.51 (1 H, br s), 7.35 (1 H, dd), 5. 77 (1 H, br s).
参考製造例２
　２８．５ｇの中間体１及びＴＨＦ１８０ｍＬの混合物に窒素雰囲気下－７８℃で水素化ナトリウム（６０％、油性）７．５７ｇを加え、次にエタンチオール１３．３ｍＬを加えた。得られた混合物を－３０℃までゆっくり昇温し、同温で１時間撹拌した。該混合物を室温にし、減圧下で濃縮した。得られた固体を水で洗浄した後、乾燥し、次式で示される中間体２を２７．４ｇ得た。
Figure JPOXMLDOC01-appb-C000042
 中間体２：1H-NMR (DMSO-d6) δ: 8.53 (1H, d), 8.28 (1H, br s), 7.93 (1H, dd), 9.78 (1H, brs), 3.14 (2H, q), 1.50 (3H, t). Reference Production Example 2
To a mixture of 28.5 g of Intermediate 1 and 180 mL of THF was added 7.57 g of sodium hydride (60%, oily) at -78 ° C. under a nitrogen atmosphere, followed by 13.3 mL of ethanethiol. The resulting mixture was slowly warmed to −30 ° C. and stirred at the same temperature for 1 hour. The mixture was brought to room temperature and concentrated under reduced pressure. The obtained solid was washed with water and then dried to obtain 27.4 g of Intermediate 2 represented by the following formula.
Figure JPOXMLDOC01-appb-C000042
 Intermediate 2: 1 H-NMR (DMSO-d 6 ) δ: 8.53 (1 H, d), 8. 28 (1 H, br s), 7. 93 (1 H, dd), 9. 78 (1 H, brs), 3. 14 (2 H, q ), 1.50 (3H, t).
参考製造例３
　２３．７ｇの中間体２、トリエチルアミン４９．３ｍＬ及びクロロホルム１００ｍＬの混合物に０℃でトリフルオロメタンスルホン酸無水物５０．２ｍＬを加え、１時間撹拌した。得られた混合物に室温で水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、次式で示される中間体３を１８．４ｇ得た。
Figure JPOXMLDOC01-appb-C000043
 中間体３：1H-NMR (CDCl3) δ: 8.30 (1H, d), 7.40 (1H, dd), 3.07 (2H, q), 1.42 (3H, t). Reference Production Example 3
To a mixture of 23.7 g of Intermediate 2, 49.3 mL of triethylamine and 100 mL of chloroform, 50.2 mL of trifluoromethanesulfonic anhydride was added at 0 ° C. and stirred for 1 hour. To the resulting mixture was added water at room temperature and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 18.4 g of Intermediate 3 represented by the following formula.
Figure JPOXMLDOC01-appb-C000043
 Intermediate 3: 1 H-NMR (CDCl 3 ) δ: 8.30 (1 H, d), 7.40 (1 H, dd), 3.07 (2 H, q), 1.42 (3 H, t).
参考製造例３－１
　２－シアノ－３－フルオロ－５－クロロピリジン１．０ｇ、水素化ナトリウム（６０％、油性）３８５ｍｇ及びＴＨＦ３２ｍＬの混合物に－７８℃でエタンチオール４６２μＬを加えた後、撹拌しながら、２時間かけて室温まで昇温した。得られた混合物に水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、次式で示される中間体３－１を９６３ｍｇ得た。
Figure JPOXMLDOC01-appb-C000044
 中間体３－１：1H-NMR (CDCl3) δ: 8.39 (1H, d), 7.66 (1H, d), 3.07 (2H, q), 1.42 (3H, t). Reference Production Example 3-1
After adding 462 μL of ethanethiol at -78 ° C to a mixture of 1.0 g of 2-cyano-3-fluoro-5-chloropyridine, 385 mg of sodium hydride (60%, oily) and 32 mL of THF, stirring is performed for 2 hours The temperature was raised to room temperature. To the resulting mixture was added water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 963 mg of Intermediate 3-1 represented by the following formula.
Figure JPOXMLDOC01-appb-C000044
 Intermediate 3-1: 1 H-NMR (CDCl 3 ) δ: 8.39 (1 H, d), 7.66 (1 H, d), 3.07 (2 H, q), 1.42 (3 H, t).
参考製造例４
　１８．４１ｇの中間体３、ｔｅｒｔ－ブチルアルコール１０．３ｍＬ及びＤＭＦ５０ｍＬの混合物に６０℃で水素化ナトリウム（６０％、油性）４．４４ｇを加え、１時間撹拌した。得られた混合物を室温にし、水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、次式で示される中間体４を１４．２ｇ得た。
Figure JPOXMLDOC01-appb-C000045
 中間体４：1H-NMR (CDCl3) δ: 8.17 (1H, d), 7.26 (1H, d), 3.05 (2H, q), 1.46 (9H, s), 1.38 (3H, t). Reference Production Example 4
To a mixture of 18.41 g of intermediate 3, 10.3 mL of tert-butyl alcohol and 50 mL of DMF was added 4.44 g of sodium hydride (60%, oily) at 60 ° C. and stirred for 1 hour. The resulting mixture was brought to room temperature, water was added and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 14.2 g of Intermediate 4 represented by the following formula.
Figure JPOXMLDOC01-appb-C000045
 Intermediate 4: 1 H-NMR (CDCl 3 ) δ: 8.17 (1H, d), 7.26 (1H, d), 3.05 (2H, q), 1.46 (9H, s), 1.38 (3H, t).
参考製造例４－１
　２．５１ｇの中間体３－１、水素化ナトリウム（６０％、油性）６１４ｍｇ及びＤＭＦ３０ｍＬの混合物に室温下、エタノール８２０μＬを加え、１時間撹拌した。得られた混合物に水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、次式で示される中間体４－１を１．４７ｇ得た。
Figure JPOXMLDOC01-appb-C000046
 中間体４－１：1H-NMR (CDCl3) δ: 8.13 (1H, d), 7.13 (1H, d), 4.15 (2H, q), 3.04 (2H, q), 1.48 (3H, t), 1.38 (3H, t). Reference Production Example 4-1
To a mixture of 2.51 g of intermediate 3-1, 614 mg of sodium hydride (60%, oily) and 30 mL of DMF was added 820 μL of ethanol at room temperature and stirred for 1 hour. To the resulting mixture was added water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 1.47 g of Intermediate 4-1 represented by the following formula.
Figure JPOXMLDOC01-appb-C000046
 Intermediate 4-1: 1 H-NMR (CDCl 3 ) δ: 8.13 (1 H, d), 7. 13 ( 1 H, d), 4. 15 (2 H, q), 3.04 (2 H, q), 1. 48 (3 H, t) , 1.38 (3H, t).
参考製造例４－２
　１．４７ｇの中間体４－１及びクロロホルム７０ｍＬの混合物に室温下、ｍＣＰＢＡ３．５８ｇを加え、５日間撹拌した。得られた混合物に飽和チオ硫酸ナトリウム水溶液及び飽和重曹水を加え、クロロホルムで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、次式で示される中間体４－２を２．１８ｇ得た。
Figure JPOXMLDOC01-appb-C000047
 中間体４－２：1H-NMR (CDCl3) δ: 8.55 (1H, d), 7.80 (1H, d), 4.25 (2H, q), 3.48 (2H, q), 1.52 (3H, t), 1.37 (3H, t). Reference Production Example 4-2
At room temperature, 3.58 g of mCPBA was added to a mixture of 1.47 g of Intermediate 4-1 and 70 mL of chloroform, and the mixture was stirred for 5 days. To the resulting mixture were added saturated aqueous sodium thiosulfate solution and saturated aqueous sodium bicarbonate solution, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 2.18 g of Intermediate 4-2 represented by the following formula.
Figure JPOXMLDOC01-appb-C000047
 Intermediate 4-2: 1 H-NMR (CDCl 3 ) δ: 8.55 (1H, d), 7.80 (1H, d), 4.25 (2H, q), 3.48 (2H, q), 1.52 (3H, t) , 1.37 (3H, t).
参考製造例４－３
　１．６７ｇの中間体４－２、水５ｍＬ及び硫酸５ｍＬの混合物を１００℃で３時間撹拌した。得られた混合物を水に加え、析出した結晶をろ取し、乾燥して、次式で示される中間体４－３を５８１ｍｇ得た。
Figure JPOXMLDOC01-appb-C000048
 中間体４－３：1H-NMR (DMSO-d6) δ: 13.72 (1H, br s), 8.58 (1H, d), 7.74 (1H, d), 4.27 (2H, q), 3.58 (2H, q), 1.38 (3H, t), 1.19 (3H, t). Reference Production Example 4-3
A mixture of 1.67 g of Intermediate 4-2, 5 mL of water and 5 mL of sulfuric acid was stirred at 100 ° C. for 3 hours. The resulting mixture was added to water, and the precipitated crystals were collected by filtration and dried to give 581 mg of an intermediate 4-3 represented by the following formula.
Figure JPOXMLDOC01-appb-C000048
 Intermediate 4-3: 1 H-NMR (DMSO-d 6 ) δ: 13. 72 (1 H, br s), 8. 58 (1 H, d), 7.74 (1 H, d) , q), 1.38 (3H, t), 1.19 (3H, t).
参考製造例５
　１４．２ｇの中間体４及びエタノール２０ｍＬの混合物に室温で１２Ｎ水酸化ナトリウム水溶液２０ｍＬを加え、６０℃で３時間撹拌した。得られた混合物に１２Ｎ塩酸をｐＨが１になるまで加えた。析出した固体をろ取し、水で洗浄した後、乾燥し、次式で示される中間体５を１３．４ｇ得た。
Figure JPOXMLDOC01-appb-C000049
 中間体５：1H-NMR (CDCl3) δ: 7.98 (1H, d), 7.25 (1H, d), 2.92 (2H, q), 1.47 (9H, s), 1.44 (3H, t). Reference Production Example 5
To a mixture of 14.2 g of Intermediate 4 and 20 mL of ethanol was added 20 mL of a 12 N aqueous solution of sodium hydroxide at room temperature, and the mixture was stirred at 60 ° C. for 3 hours. To the resulting mixture was added 12 N hydrochloric acid until the pH was 1. The precipitated solid was collected by filtration, washed with water and dried to give 13.4 g of Intermediate 5 represented by the following formula.
Figure JPOXMLDOC01-appb-C000049
 Intermediate 5: 1 H-NMR (CDCl 3 ) δ: 7.98 (1 H, d), 7. 25 ( 1 H, d), 2. 92 (2 H, q), 1. 47 (9 H, s), 1. 44 (3 H, t).
参考製造例６
　参考製造例４及び５に準じて製造した化合物及びその物性値を以下に示す。
Figure JPOXMLDOC01-appb-C000050
 中間体６：1H-NMR (CDCl3) δ: 8.24 (1H, d), 7.58 (1H, d), 3.15 (2H, q), 1.56 (6H, s), 1.37 (3H, t). Reference Production Example 6
The compounds produced according to Reference Production Examples 4 and 5 and the physical properties thereof are shown below.
Figure JPOXMLDOC01-appb-C000050
 Intermediate 6: 1 H-NMR (CDCl 3 ) δ: 8.24 (1H, d), 7.58 (1H, d), 3.15 (2H, q), 1.56 (6H, s), 1.37 (3H, t).
参考製造例７
　２．０ｇの中間体５、４－（トリフルオロメタンスルホニル）－２－アミノフェノール１．８ｇ及びピリジン１０ｍＬの混合物に室温で１－［３－（ジメチルアミノ）プロピル］－３－エチルカルボジイミド塩酸塩１．６６ｇ及び１－ヒドロキシベンゾトリアゾール５０ｍｇを加え、６０℃で２時間撹拌した。得られた混合物を室温にし、水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮し、次式で示される中間体７を２．１ｇ得た。
Figure JPOXMLDOC01-appb-C000051
 中間体７：1H-NMR (CDCl3) δ: 10.40 (1H, s), 8.07 (1H, d), 7.79-7.78 (1H, m), 7.76-7.74 (1H, m), 7.28-7.27 (1H, m), 7.22-7.22 (1H, m), 2.93 (2H, q), 1.51 (9H, s), 1.45 (3H, t). Reference Production Example 7
1- [3- (Dimethylamino) propyl] -3-ethylcarbodiimide hydrochloride 1 at room temperature in a mixture of 2.0 g of intermediate 5, 1.8 g of 4- (trifluoromethanesulfonyl) -2-aminophenol and 10 mL of pyridine .66 g and 50 mg of 1-hydroxybenzotriazole were added and stirred at 60.degree. C. for 2 hours. The resulting mixture was brought to room temperature, water was added and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 2.1 g of Intermediate 7 represented by the following formula.
Figure JPOXMLDOC01-appb-C000051
 Intermediate 7: 1 H-NMR (CDCl 3 ) δ: 10.40 (1H, s), 8.07 (1H, d), 7.79-7.78 (1H, m), 7.76-7.74 (1H, m), 7.28-7.27 ( 1H, m), 7.22-7.22 (1H, m), 2.93 (2H, q), 1.51 (9H, s), 1.45 (3H, t).
参考製造例８
　参考製造例７に準じて製造した化合物及びその物性値を以下に示す。
　式（Ａ－１）：
Figure JPOXMLDOC01-appb-C000052
 で示される化合物において、Ｒ1及びＲの組合せが［表４］に記載のいずれかの組合せである化合物。 Reference Production Example 8
The compounds produced according to Reference Production Example 7 and the physical properties thereof are shown below.
Formula (A-1):
Figure JPOXMLDOC01-appb-C000052
 In the compounds shown by, the combination of R 1 and R is any combination described in [Table 4].
Figure JPOXMLDOC01-appb-T000053
 　中間体８：1H-NMR (CDCl3) δ: 10.26 (1H, s), 9.78 (1H, br s), 8.04 (1H, d), 7.46 (1H, d), 7.37 (1H, dd), 7.27 (1H, d), 7.11 (1H, d), 2.92 (2H, q), 1.48 (9H, s), 1.44 (3H, t).
　中間体９：1H-NMR (CDCl3) δ: 10.21 (1H, s), 9.84 (1H, br s), 8.05 (1H, d), 7.50 (1H, d), 7.39 (1H, dd), 7.27 (1H, d), 7.07 (1H, d), 2.92 (2H, q), 1.48 (9H, s), 1.44 (3H, t).
　中間体１０：1H-NMR (CDCl3) δ: 10.45 (1H, s), 8.09 (1H, d), 8.07 (1H, d), 7.73 (1H, dd), 7.36 (1H, d), 7.20 (1H, d), 2.93 (2H, q), 1.56 (6H, s), 1.45 (3H, t).
Figure JPOXMLDOC01-appb-T000053
 Intermediate 8: 1 H-NMR (CDCl 3 ) δ: 10.26 (1 H, s), 9. 78 (1 H, br s), 8.04 (1 H, d), 7.46 (1 H, d), 7. 37 (1 H, dd), 7.27 (1 H, d), 7.11 (1 H, d), 2. 92 (2 H, q), 1. 48 (9 H, s), 1. 44 (3 H, t).
Intermediate 9: 1 H-NMR (CDCl 3 ) δ: 10.21 (1 H, s), 9. 84 (1 H, br s), 8.05 (1 H, d), 7. 50 (1 H, d), 7. 39 (1 H, dd), 7.27 (1 H, d), 7.07 (1 H, d), 2. 92 (2 H, q), 1. 48 (9 H, s), 1. 44 (3 H, t).
Intermediate 10: 1 H-NMR (CDCl 3 ) δ: 10.45 (1 H, s), 8.09 (1 H, d), 8.07 (1 H, d), 7.73 (1 H, dd), 7.36 (1 H, d), 7.20 (1H, d), 2.93 (2H, q), 1.56 (6H, s), 1.45 (3H, t).
製造例１
　２．１ｇの中間体７、ビス（２－メトキシエチル）＝アゾジカルボキシラート１．２３ｇ及びＴＨＦ２０ｍＬの混合物に室温でトリフェニルホスフィン１．３８ｇを加え、６０℃で１時間撹拌した。得られた混合物を室温にし、水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルクロマトグラフィー（ヘキサン：酢酸エチル＝２：１）に付し、次式で示される本発明化合物１を１．２７ｇ得た。
Figure JPOXMLDOC01-appb-C000054
 本発明化合物１：1H-NMR (CDCl3) δ: 8.62 (1H, d), 8.31 (1H, d), 8.09 (1H, dd), 7.91 (1H, d), 7.34 (1H, d), 3.04 (2H, q), 1.51 (9H, s), 1.49 (3H, t). Production Example 1
To a mixture of 2.1 g of intermediate 7, bis (2-methoxyethyl) = 1.23 g of azodicarboxylate and 20 mL of THF was added 1.38 g of triphenylphosphine at room temperature and stirred at 60 ° C. for 1 hour. The resulting mixture was brought to room temperature, water was added and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography (hexane: ethyl acetate = 2: 1) to obtain 1.27 g of the present compound 1 represented by the following formula.
Figure JPOXMLDOC01-appb-C000054
 The present compound 1: 1 H-NMR (CDCl 3 ) δ: 8.62 (1 H, d), 8.31 (1 H, d), 8.09 (1 H, dd), 7. 91 (1 H, d), 7.34 (1 H, d), 3.04 (2H, q), 1.51 (9H, s), 1.49 (3H, t).
製造例２
　製造例１に準じて製造した化合物及びその物性値を以下に示す。
　式（Ａ－２）：
Figure JPOXMLDOC01-appb-C000055
 で示される化合物において、Ｒ1及びＲの組合せが［表５］に記載のいずれかの組合せである化合物。 Production Example 2
The compounds produced according to Production Example 1 and the physical properties thereof are shown below.
Formula (A-2):
Figure JPOXMLDOC01-appb-C000055
 In the compounds shown by, the combination of R 1 and R is any combination described in [Table 5].
Figure JPOXMLDOC01-appb-T000056
　本発明化合物２：1H-NMR (CDCl3) δ: 8.30 (1H, d), 8.19 (1H, d), 7.75 (1H, dd), 7.66 (1H, d), 7.32 (1H, d), 3.02 (2H, q), 1.48 (9H, s), 1.47 (3H, t).
　本発明化合物３：1H-NMR (CDCl3) δ: 8.29 (1H, d), 8.23 (1H, d), 7.69-7.69 (2H, m), 7.32 (1H, d), 3.02 (2H, q), 1.48 (9H, s), 1.48 (3H, t).
　本発明化合物４：1H-NMR (CDCl3) δ: 8.64 (1H, d), 8.32 (1H, d), 8.11 (1H, dd), 7.93 (1H, d), 7.43 (1H, d), 3.05 (2H, q), 1.58 (6H, s), 1.49 (3H, t).
Figure JPOXMLDOC01-appb-T000056
The present compound 2: 1 H-NMR (CDCl 3 ) δ: 8.30 (1 H, d), 8. 19 (1 H, d), 7. 75 (1 H, dd), 7. 66 (1 H, d), 7.32 (1 H, d), 3.02 (2H, q), 1.48 (9H, s), 1.47 (3H, t).
The present compound 3: 1 H-NMR (CDCl 3 ) δ: 8.29 (1 H, d), 8.23 (1 H, d), 7.69-7.69 (2 H, m), 7.32 (1 H, d), 3.02 (2 H, q ), 1.48 (9H, s), 1.48 (3H, t).
The present compound 4: 1 H-NMR (CDCl 3 ) δ: 8.64 (1H, d), 8.32 (1H, d), 8.11 (1H, dd), 7.93 (1H, d), 7.43 (1H, d), 3.05 (2H, q), 1.58 (6H, s), 1.49 (3H, t).
製造例３
　７００ｍｇの本発明化合物１及びクロロホルム１０ｍＬの混合物にｍＣＰＢＡ（７０％）７３５ｍｇを加え、室温で３時間撹拌した。得られた混合物に飽和チオ硫酸ナトリウム水溶液と飽和重曹水を加え、クロロホルムで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルクロマトグラフィー（ヘキサン：酢酸エチル＝２：１）に付し、次式で示される本発明化合物５を５６４ｍｇ得た。
Figure JPOXMLDOC01-appb-C000057
 本発明化合物５：1H-NMR (CDCl3) δ: 8.67 (1H, d), 8.55 (1H, d), 8.15-8.13 (2H, m), 7.93 (1H, d), 4.03 (2H, q), 1.56 (9H, s), 1.44 (3H, t). Production Example 3
735 mg of mCPBA (70%) was added to a mixture of 700 mg of the compound of the present invention 1 and 10 mL of chloroform, and the mixture was stirred at room temperature for 3 hours. To the resulting mixture were added saturated aqueous sodium thiosulfate solution and saturated aqueous sodium bicarbonate solution, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography (hexane: ethyl acetate = 2: 1) to obtain 564 mg of the present compound 5 represented by the following formula.
Figure JPOXMLDOC01-appb-C000057
 The present compound 5: 1 H-NMR (CDCl 3 ) δ: 8.67 (1 H, d), 8.55 (1 H, d), 8.15-8.13 (2 H, m), 7. 93 (1 H, d), 4.03 (2 H, q ), 1.56 (9H, s), 1.44 (3H, t).
製造例４
　製造例３に準じて製造した化合物及びその物性値を以下に示す。
　式（Ａ－３）：
Figure JPOXMLDOC01-appb-C000058
 で示される化合物において、Ｒ1及びＲの組合せが［表６］に記載のいずれかの組合せである化合物。 Production Example 4
The compounds produced according to Production Example 3 and the physical properties thereof are shown below.
Formula (A-3):
Figure JPOXMLDOC01-appb-C000058
 And in the compound represented by, the combination of R 1 and R is any combination described in [Table 6].
Figure JPOXMLDOC01-appb-T000059
 　本発明化合物６：1H-NMR (CDCl3) δ: 8.66 (1H, d), 8.15 (1H, d), 8.13 (1H, d), 7.77 (1H, d), 7.72 (1H, dd), 4.05 (2H, q), 1.54 (9H, s), 1.43 (3H, t).
　本発明化合物７：1H-NMR (CDCl3) δ: 8.66 (1H, d), 8.16-8.15 (2H, m), 7.74-7.71 (2H, m), 4.05 (2H, q), 1.54 (9H, s), 1.41 (3H, q).
　本発明化合物８：1H-NMR (CDCl3) δ: 8.67 (1H, d), 8.32 (1H, d), 8.15 (1H, d), 7.90 (1H, d), 7.86 (1H, dd), 4.05 (2H, q), 1.55 (9H, s), 1.44 (3H, t).
　本発明化合物９：1H-NMR (CDCl3) δ: 8.74 (1H, d), 8.58 (1H, d), 8.22 (1H, d), 8.17 (1H, dd), 7.95 (1H, d), 4.02 (2H, q), 1.64 (6H, s), 1.45 (3H, t).
Figure JPOXMLDOC01-appb-T000059
 The present compound 6: 1 H-NMR (CDCl 3 ) δ: 8.66 (1H, d), 8.15 (1H, d), 8.13 (1H, d), 7.77 (1H, d), 7.72 (1H, dd), 4.05 (2H, q), 1.54 (9H, s), 1.43 (3H, t).
The present compound 7: 1 H-NMR (CDCl 3 ) δ: 8.66 (1H, d), 8.16-8.15 (2H, m), 7.74-7.71 (2H, m), 4.05 (2H, q), 1.54 (9H , s), 1.41 (3H, q).
The present compound 8: 1 H-NMR (CDCl 3 ) δ: 8.67 (1 H, d), 8.32 (1 H, d), 8. 15 ( 1 H, d), 7. 90 (1 H, d), 7. 86 (1 H, dd), 4.05 (2H, q), 1.55 (9H, s), 1.44 (3H, t).
The present compound 9: 1 H-NMR (CDCl 3 ) δ: 8.74 (1H, d), 8.58 (1H, d), 8.22 (1H, d), 8.17 (1H, dd), 7.95 (1H, d), 4.02 (2H, q), 1.64 (6H, s), 1.45 (3H, t).
製造例５
　４８４ｍｇの本発明化合物６及びクロロホルム１．２ｍＬの混合物に０℃でトリフルオロ酢酸１．２ｍＬを加え、室温で３時間撹拌した。得られた混合物を減圧下で濃縮した。得られた残渣にＤＭＦ３ｍＬを加え、次にヨードエタン３２３μＬ及び炭酸セシウム１．３２ｇを順次加え、室温で３時間撹拌した。得られた混合物に水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルクロマトグラフィー（ヘキサン：酢酸エチル＝２：１）に付し、次式で示される本発明化合物１０を２４８ｍｇ得た。
Figure JPOXMLDOC01-appb-C000060
 本発明化合物１０：1H-NMR (CDCl3) δ: 8.65 (1H, d), 8.12 (1H, d), 8.01 (1H, d), 7.76 (1H, d), 7.71 (1H, dd), 4.29 (2H, q), 4.06 (2H, q), 1.54 (3H, t), 1.44 (3H, t). Production Example 5
1.2 mL of trifluoroacetic acid was added to a mixture of 484 mg of the compound 6 of the present invention and 1.2 mL of chloroform at 0 ° C., and the mixture was stirred at room temperature for 3 hours. The resulting mixture was concentrated under reduced pressure. 3 mL of DMF was added to the obtained residue, then, 323 μL of iodoethane and 1.32 g of cesium carbonate were sequentially added, and the mixture was stirred at room temperature for 3 hours. To the resulting mixture was added water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography (hexane: ethyl acetate = 2: 1) to obtain 248 mg of the present compound 10 represented by the following formula.
Figure JPOXMLDOC01-appb-C000060
 The present compound 10: 1 H-NMR (CDCl 3 ) δ: 8.65 (1 H, d), 8.12 (1 H, d), 8.01 (1 H, d), 7. 76 (1 H, d), 7.71 (1 H, dd), 4.29 (2H, q), 4.06 (2H, q), 1.54 (3H, t), 1.44 (3H, t).
製造例６
　製造例５に準じて製造した化合物及びその物性値を以下に示す。
　式（Ａ－４）：
Figure JPOXMLDOC01-appb-C000061
 で示される化合物において、Ｒ1及びＲ2の組合せが［表７］に記載のいずれかの組合せである化合物。 Production Example 6
The compounds produced according to Production Example 5 and the physical properties thereof are shown below.
Formula (A-4):
Figure JPOXMLDOC01-appb-C000061
 In the compounds shown by, the combination of R 1 and R 2 is any combination described in [Table 7].
Figure JPOXMLDOC01-appb-T000062
 　本発明化合物１１：1H-NMR (CDCl3) δ: 8.65 (1H, d), 8.55 (1H, d), 8.14 (1H, dd), 8.01 (1H, d), 7.93 (1H, d), 4.30 (2H, q), 4.03 (2H, q), 1.54 (3H, t), 1.45 (3H, t).
　本発明化合物１２：1H-NMR (CDCl3) δ: 8.66 (1H, d), 8.55 (1H, d), 8.14 (1H, dd), 8.02 (1H, d), 7.93 (1H, d), 4.18 (2H, t), 4.03 (2H, q), 1.95-1.92 (2H, m), 1.45 (3H, t), 1.12 (3H, t).
　本発明化合物１３：1H-NMR (CDCl3) δ: 8.62 (1H, d), 8.54 (1H, d), 8.14 (1H, dd), 7.99 (1H, d), 7.93 (1H, d), 4.86-4.80 (1H, m), 4.04 (2H, q), 1.48 (6H, d), 1.45 (3H, t).
　本発明化合物１４：1H-NMR (CDCl3) δ: 8.76 (1H, d), 8.57 (1H, d), 8.16 (1H, dd), 8.11 (1H, d), 7.95 (1H, d), 4.69 (2H, t), 4.06 (2H, q), 1.47 (3H, t).
　本発明化合物１５：1H-NMR (CDCl3) δ: 8.66 (1H, d), 8.55 (1H, d), 8.14 (1H, dd), 8.01 (1H, d), 7.93 (1H, d), 4.04 (2H, q), 3.97 (2H, d), 2.24-2.19 (1H, m), 1.46 (3H, t), 1.10 (6H, d).
　本発明化合物１６：1H-NMR (CDCl3) δ: 8.64 (1H, d), 8.15 (1H, d), 8.01 (1H, d), 7.74 (1H, dd), 7.70 (1H, d), 4.28 (2H, q), 4.07 (2H, q), 1.54 (3H, t), 1.43 (3H, t).
　本発明化合物１７：1H-NMR (CDCl3) δ: 8.65 (1H, d), 8.15 (1H, d), 8.01 (1H, d), 7.74-7.71 (2H, m), 4.16 (2H, t), 4.07 (2H, q), 1.94-1.91 (2H, m), 1.44 (3H, t), 1.11 (3H, t).
　本発明化合物１８：1H-NMR (CDCl3) δ: 8.60 (1H, d), 8.15 (1H, d), 7.99 (1H, d), 7.74-7.70 (2H, m), 4.86-4.77 (1H, m), 4.07 (2H, q), 1.46 (6H, d), 1.43 (3H, t).
　本発明化合物１９：1H-NMR (CDCl3) δ: 8.65 (1H, d), 8.12 (1H, s), 8.01 (1H, d), 7.76 (1H, d), 7.71 (1H, d), 4.16 (2H, t), 4.06 (2H, q), 1.95-1.91 (2H, m), 1.44 (3H, t), 1.11 (3H, t).
　本発明化合物２０：1H-NMR (CDCl3) δ: 8.61 (1H, d), 8.12 (1H, d), 7.99 (1H, d), 7.76 (1H, d), 7.71 (1H, dd), 4.87-4.78 (1H, m), 4.07 (2H, q), 1.47 (6H, d), 1.44 (3H, t).
　本発明化合物２１：1H-NMR (CDCl3) δ: 8.65 (1H, d), 8.31 (1H, s), 8.01 (1H, d), 7.90 (1H, d), 7.85 (1H, d), 4.29 (2H, q), 4.06 (2H, q), 1.55 (3H, t), 1.44 (3H, t).
　本発明化合物２２：1H-NMR (CDCl3) δ: 8.66 (1H, d), 8.32 (1H, d), 8.02 (1H, d), 7.90-7.85 (2H, m), 4.17 (2H, t), 4.06 (2H, q), 1.95-1.92 (2H, m), 1.45 (3H, t), 1.11 (3H, t).
　本発明化合物２３：1H-NMR (CDCl3) δ: 8.61 (1H, d), 8.31 (1H, d), 8.00 (1H, d), 7.90-7.85 (2H, m), 4.87-4.78 (1H, m), 4.06 (2H, q), 1.47 (6H, d), 1.44 (3H, t).
　本発明化合物６３：1H-NMR (CDCl3) δ: 8.64 (1H, d), 8.00 (1H, d), 7.69 (1H, d), 7.66 (1H, d), 7.32 (1H, dd), 4.28 (2H, q), 4.06 (2H, q), 1.53 (3H, t), 1.43 (3H, t).
　本発明化合物６４：1H-NMR (CDCl3) δ: 8.64 (1H, d), 8.01 (1H, d), 7.69 (1H, d), 7.66 (1H, d), 7.32 (1H, dd), 4.16 (2H, t), 4.06 (2H, q), 1.94-1.91 (2H, m), 1.43 (3H, t), 1.11 (3H, t).
　本発明化合物６５：1H-NMR (CDCl3) δ: 8.60 (1H, d), 7.98 (1H, d), 7.69 (1H, d), 7.66 (1H, d), 7.31 (1H, dd), 4.86-4.77 (1H, m), 4.06 (2H, q), 1.48-1.40 (9H, m).
Figure JPOXMLDOC01-appb-T000062
 The present compound 11: 1 H-NMR (CDCl 3 ) δ: 8.65 (1 H, d), 8.55 (1 H, d), 8. 14 (1 H, dd), 8.01 (1 H, d), 7. 93 (1 H, d), 4.30 (2H, q), 4.03 (2H, q), 1.54 (3H, t), 1.45 (3H, t).
The present compound 12: 1 H-NMR (CDCl 3 ) δ: 8.66 (1H, d), 8.55 (1H, d), 8.14 (1H, dd), 8.02 (1H, d), 7.93 (1H, d), 4.18 (2H, t), 4.03 (2H, q), 1.95-1.92 (2H, m), 1.45 (3H, t), 1.12 (3H, t).
Invention compound 13: 1 H-NMR (CDCl 3 ) δ: 8.62 (1H, d), 8.54 (1H, d), 8.14 (1H, dd), 7.99 (1H, d), 7.93 (1H, d), 4.86-4.80 (1 H, m), 4.04 (2 H, q), 1. 48 (6 H, d), 1. 45 (3 H, t).
The present compound 14: 1 H-NMR (CDCl 3 ) δ: 8.76 (1H, d), 8.57 (1H, d), 8.16 (1H, dd), 8.11 (1H, d), 7.95 (1H, d), 4.69 (2H, t), 4.06 (2H, q), 1.47 (3H, t).
Invention compound 15: 1 H-NMR (CDCl 3 ) δ: 8.66 (1 H, d), 8.55 (1 H, d), 8. 14 (1 H, dd), 8.01 (1 H, d), 7. 93 (1 H, d), 4.04 (2H, q), 3.97 (2H, d), 2.24-2.19 (1 H, m), 1.46 (3 H, t), 1.10 (6 H, d).
The present compound 16: 1 H-NMR (CDCl 3 ) δ: 8.64 (1H, d), 8.15 (1H, d), 8.01 (1H, d), 7.74 (1H, dd), 7.70 (1H, d), 4.28 (2H, q), 4.07 (2H, q), 1.54 (3H, t), 1.43 (3H, t).
The present compound 17: 1 H-NMR (CDCl 3 ) δ: 8.65 (1H, d), 8.15 (1H, d), 8.01 (1H, d), 7.74-7.71 (2H, m), 4.16 (2H, t) ), 4.07 (2H, q), 1.94-1.91 (2H, m), 1.44 (3H, t), 1.11 (3H, t).
The present compound 18: 1 H-NMR (CDCl 3 ) δ: 8.60 ( 1 H, d), 8. 15 (1 H, d), 7.99 (1 H, d), 7.74-7.70 (2 H, m), 4.86-4. 77 (1 H , m), 4.07 (2H, q), 1.46 (6H, d), 1.43 (3H, t).
The present compound 19: 1 H-NMR (CDCl 3 ) δ: 8.65 (1H, d), 8.12 (1H, s), 8.01 (1H, d), 7.76 (1H, d), 7.71 (1H, d), 4.16 (2 H, t), 4.06 (2 H, q), 1.95-1. 91 (2 H, m), 1. 44 (3 H, t), 1. 11 (3 H, t).
The present compound 20: 1 H-NMR (CDCl 3 ) δ: 8.61 (1H, d), 8.12 (1H, d), 7.99 (1H, d), 7.76 (1H, d), 7.71 (1H, dd), 4.87-4.78 (1H, m), 4.07 (2H, q), 1.47 (6H, d), 1.44 (3H, t).
The present compound 21: 1 H-NMR (CDCl 3 ) δ: 8.65 (1H, d), 8.31 (1H, s), 8.01 (1H, d), 7.90 (1H, d), 7.85 (1H, d), 4.29 (2H, q), 4.06 (2H, q), 1.55 (3H, t), 1.44 (3H, t).
The present compound 22: 1 H-NMR (CDCl 3 ) δ: 8.66 (1 H, d), 8.32 (1 H, d), 8.02 (1 H, d), 7. 90-7. 85 (2 H, m), 4. 17 (2 H, t ), 4.06 (2H, q), 1.95-1.92 (2H, m), 1.45 (3H, t), 1.11 (3H, t).
Invention compound 23: 1 H-NMR (CDCl 3 ) δ: 8.61 (1H, d), 8.31 (1H, d), 8.00 (1H, d), 7.90-7.85 (2H, m), 4.87-4.78 (1H , m), 4.06 (2H, q), 1.47 (6H, d), 1.44 (3H, t).
The present compound 63: 1 H-NMR (CDCl 3 ) δ: 8.64 (1 H, d), 8.00 (1 H, d), 7. 69 (1 H, d), 7. 66 (1 H, d), 7.32 (1 H, dd), 4.28 (2H, q), 4.06 (2H, q), 1.53 (3H, t), 1.43 (3H, t).
The present compound 64: 1 H-NMR (CDCl 3 ) δ: 8.64 (1H, d), 8.01 (1H, d), 7.69 (1H, d), 7.66 (1H, d), 7.32 (1H, dd), 4.16 (2H, t), 4.06 (2H, q), 1.94-1.91 (2H, m), 1.43 (3H, t), 1.11 (3H, t).
The present compound 65: 1 H-NMR (CDCl 3 ) δ: 8.60 (1 H, d), 7. 98 (1 H, d), 7. 69 (1 H, d), 7. 66 (1 H, d), 7.31 (1 H, dd), 4.86-4.77 (1 H, m), 4.06 (2 H, q), 1.48-1.40 (9 H, m).
製造例７
　２－［５－フルオロ－３－（エタンスルホニル）ピリジン－２－イル］－３－メチル－６－（トリフルオロメチル）－３Ｈ－イミダゾ［４，５－ｂ］ピリジン４００ｍｇ、２，２，３，３－テトラフルオロ－１－プロパノール９１μＬ及びＮＭＰ１ｍＬの混合物に、窒素雰囲気下室温で水素化ナトリウム（６０％、油性）６２ｍｇを加え、３時間撹拌した。得られた混合物に水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルクロマトグラフィー（ヘキサン：酢酸エチル＝２：１）に付し、次式で示される本発明化合物２４を３０９ｍｇ得た。
Figure JPOXMLDOC01-appb-C000063
 本発明化合物２４：1H-NMR (CDCl3) δ: 8.76 (1H, d), 8.73 (1H, d), 8.30 (1H, d), 8.04 (1H, d), 6.08 (1H, tt), 4.62 (2H, t), 3.89 (2H, q), 3.87 (3H, s), 1.39 (3H, t). Production Example 7
2- [5-Fluoro-3- (ethanesulfonyl) pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine 400 mg, 2,2,3 62 mg of sodium hydride (60%, oily) was added to a mixture of 91 μL of 3, 3-tetrafluoro-1-propanol and 1 mL of NMP at room temperature under a nitrogen atmosphere, and stirred for 3 hours. To the resulting mixture was added water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography (hexane: ethyl acetate = 2: 1) to obtain 309 mg of the present compound 24 represented by the following formula.
Figure JPOXMLDOC01-appb-C000063
 The present compound 24: 1 H-NMR (CDCl 3 ) δ: 8.76 ( 1 H, d), 8. 73 (1 H, d), 8. 30 (1 H, d), 8.04 (1 H, d), 6.08 (1 H, tt), 4.62 (2H, t), 3.89 (2H, q), 3.87 (3H, s), 1.39 (3H, t).
製造例８
　製造例７に準じて製造した化合物及びその物性値を以下に示す。
　式（Ａ－５）：
Figure JPOXMLDOC01-appb-C000064
 で示される化合物において、Ｒ2が［表８］に記載のいずれかの化合物。 Production Example 8
The compounds produced according to Production Example 7 and the physical properties thereof are shown below.
Formula (A-5):
Figure JPOXMLDOC01-appb-C000064
 In the compounds represented by, R 2 is any compound described in [Table 8].
Figure JPOXMLDOC01-appb-T000065
 本発明化合物２５：1H-NMR (CDCl3) δ: 8.75 (1H), 8.70 (1H, d), 8.30 (1H, d), 7.94 (1H, d), 4.18 (2H), 3.90-3.83 (5H, m), 1.58-1.53 (2H, m), 1.38 (3H, t), 1.26-1.20 (2H, m).
　本発明化合物２６：1H-NMR (CDCl3) δ: 8.76 (1H, d), 8.74 (1H, d), 8.31 (1H, s), 8.04 (1H, d), 4.68 (2H, t), 3.89 (2H, q), 3.87 (3H, s), 1.39 (3H, t).
　本発明化合物２７：1H-NMR (CDCl3) δ: 8.76 (1H, d), 8.73 (1H, d), 8.31 (1H, d), 8.04 (1H, d), 5.26-5.15 (1H, m), 4.71-4.55 (2H, m), 3.91 (2H, q), 3.87 (3H, s), 1.39 (3H, t).
　本発明化合物２８：1H-NMR (CDCl3) δ: 8.76 (1H, d), 8.74 (1H, d), 8.30 (1H, d), 8.04 (1H, d), 4.71 (2H, t), 3.90 (2H, q), 3.87 (3H, s), 1.39 (3H, t).
　本発明化合物２９：1H-NMR (CDCl3) δ: 8.75 (1H, s), 8.65 (1H, d), 8.29 (1H, d), 7.95 (1H, d), 4.27 (2H, t), 3.85 (3H, s), 3.85 (2H, q), 2.41-2.39 (2H, m), 2.24-2.18 (2H, m), 1.37 (3H, t).
　本発明化合物３０：1H-NMR (CDCl3) δ: 8.76 (1H, d), 8.71 (1H, d), 8.30 (1H, d), 8.03 (1H, d), 4.94-4.91 (1H, m), 3.87 (3H, s), 3.86 (2H, q), 1.66 (3H, d), 1.38 (3H, t).
　本発明化合物３１：1H-NMR (CDCl3) δ: 8.76 (1H, d), 8.74 (1H, d), 8.30 (1H, d), 8.03 (1H, d), 4.62 (2H, q), 3.88 (2H, q), 3.86 (3H, s), 1.38 (3H, t).
　本発明化合物３２：1H-NMR (CDCl3) δ: 8.75 (1H, d), 8.67 (1H, d), 8.29 (1H, d), 7.97 (1H, d), 4.44 (2H, t), 3.87 (2H, q), 3.85 (3H, s), 2.83-2.72 (2H, m), 1.38 (3H, t).
　本発明化合物３３：1H-NMR (CDCl3) δ: 8.75 (1H, d), 8.66 (1H, d), 8.29 (1H, d), 7.95 (1H, d), 4.30-4.26 (2H, m), 3.85 (2H, q), 3.85 (3H, s), 2.21-2.05 (1H, m), 1.76-1.67 (1H, m), 1.42-1.41 (1H, m), 1.37 (3H, t).
　本発明化合物３４：1H-NMR (CDCl3) δ: 8.75 (1H, d), 8.71 (1H, d), 8.30 (1H, d), 8.01 (1H, d), 6.20 (1H, tt), 4.44 (2H, td), 3.86 (2H, q), 3.86 (3H, s), 1.38 (3H, t).
　本発明化合物３５：1H-NMR (CDCl3) δ: 8.75 (1H, d), 8.63 (1H, d), 8.30 (1H, d), 7.94 (1H, d), 4.27 (2H, q), 3.86-3.81 (5H, m), 1.54 (3H, t), 1.36 (3H, t).
　本発明化合物３６：1H-NMR (CDCl3) δ: 8.74 (1H, d), 8.64 (1H, d), 8.30 (1H, d), 7.94 (1H, d), 4.16 (2H, t), 3.87-3.80 (5H, m), 1.99-1.87 (2H, m), 1.37 (3H, t), 1.11 (3H, t).
　本発明化合物３７：1H-NMR (CDCl3) δ: 8.74 (1H, dd), 8.59 (1H, d), 8.29 (1H, dd), 7.92 (1H, d), 4.84-4.78 (1H, m), 3.87-3.79 (5H, m), 1.47 (6H, d), 1.37 (3H, t).
　本発明化合物３８：1H-NMR (CDCl3) δ: 8.74 (1H, d), 8.63 (1H, d), 8.29 (1H, d), 7.94 (1H, d), 4.20 (2H, t), 3.84 (3H, s), 3.83 (2H, q), 1.92-1.85 (2H, m), 1.61-1.52 (2H, m), 1.37 (3H, t), 1.03 (3H, t).
　本発明化合物３９：1H-NMR (CDCl3) δ: 8.74 (1H, d), 8.63 (1H, d), 8.29 (1H, d), 7.93 (1H, d), 4.19 (2H, t), 3.84 (3H, s), 3.83 (2H, q), 1.94-1.87 (2H, m), 1.49-1.44 (4H, m), 1.37 (3H, t), 0.97 (3H, t).
　本発明化合物４０：1H-NMR (CDCl3) δ: 8.74 (1H, d), 8.59 (1H, d), 8.28 (1H, d), 7.92 (1H, d), 4.59-4.56 (1H, m), 3.85 (3H, s), 3.83 (2H, q), 1.91-1.71 (2H, m), 1.42 (3H, d), 1.37 (3H, t), 1.05 (3H, t).
　本発明化合物４１：1H-NMR (CDCl3) δ: 8.74 (1H, d), 8.64 (1H, d), 8.29 (1H, d), 7.94 (1H, d), 3.95 (2H, d), 3.84 (3H, s), 3.82 (2H, q), 2.26-2.16 (1H, m), 1.37 (3H, t), 1.11 (6H, d).
　本発明化合物４２：1H-NMR (CDCl3) δ: 8.74 (1H, d), 8.65 (1H, d), 8.29 (1H, d), 7.94 (1H, d), 3.84 (3H, s), 3.84 (2H, q), 3.82 (2H, s), 1.38 (3H, t), 1.12 (9H, s).
　本発明化合物４３：1H-NMR (CDCl3) δ: 8.74 (1H, d), 8.60 (1H, d), 8.28 (1H, d), 7.91 (1H, d), 4.44-4.38 (1H, m), 3.86 (3H, s), 3.83 (2H, q), 2.05-2.03 (1H, m), 1.38-1.36 (6H, m), 1.07-1.04 (6H, m).
　本発明化合物４４：1H-NMR (CDCl3) δ: 8.74 (1H, d), 8.60 (1H, d), 8.28 (1H, d), 7.92 (1H, d), 4.44-4.38 (1H, m), 3.86 (3H, s), 3.83 (2H, q), 1.80 (4H, dt), 1.37 (3H, t), 1.02 (6H, t).
　本発明化合物４５：1H-NMR (CDCl3) δ: 8.75 (1H, d), 8.64 (1H, d), 8.29 (1H, d), 8.08 (1H, d), 3.87 (3H, s), 3.82 (2H, q), 1.54 (9H, s), 1.36 (3H, t).
　本発明化合物４６：1H-NMR (CDCl3) δ: 8.75 (1H, d), 8.71 (1H, d), 8.29 (1H, d), 8.09 (1H, d), 4.95 (2H, s), 3.86 (3H, s), 3.83 (2H, q), 2.67 (1H, s), 1.38 (3H, t).
　本発明化合物４７：1H-NMR (CDCl3) δ: 8.74 (1H, s), 8.62 (1H, s), 8.28 (1H, s), 7.95 (1H, s), 5.96-5.87 (1H, m), 5.42-5.33 (2H, m), 5.05-5.02 (1H, m), 3.88 (2H, q), 3.85 (3H, s), 1.58 (3H, d), 1.35 (3H, t).
　本発明化合物４８：1H-NMR (CDCl3) δ: 8.72 (1H, s), 8.64 (1H, s), 8.27 (1H, s), 7.96 (1H, s), 4.37-4.30 (2H, m), 3.84 (2H, q), 3.82 (3H, s), 2.79-2.79 (2H, m), 2.11-2.08 (1H, m), 1.35 (3H, t).
　本発明化合物４９：1H-NMR (CDCl3) δ: 8.74 (1H, d), 8.65 (1H, d), 8.28 (1H, d), 7.93 (1H, d), 4.05 (2H, d), 3.84 (3H, s), 3.83 (2H, m), 1.35-1.39 (4H, m), 0.78-0.74 (2H, m), 0.46-0.45 (2H, m).
　本発明化合物５０：1H-NMR (CDCl3) δ: 8.74 (1H, d), 8.66 (1H, d), 8.29 (1H, d), 7.96 (1H, d), 6.10-6.06 (1H, m), 5.52-5.45 (2H, m), 4.79-4.78 (2H, m), 3.88-3.82 (5H, m), 1.36 (3H, t).
　本発明化合物５１：1H-NMR (CDCl3) δ: 8.74 (1H, d), 8.64 (1H, d), 8.29 (1H, d), 7.95 (1H, d), 5.96-5.89 (1H, m), 5.27-5.19 (2H, m), 4.25 (2H, t), 3.84 (3H, s), 3.83 (2H, q), 2.69-2.64 (2H, m), 1.37 (3H, t).
　本発明化合物５２：1H-NMR (CDCl3) δ: 8.76 (1H, d), 8.74 (1H, d), 8.30 (1H, d), 8.10 (1H, d), 7.02 (1H, d), 6.41 (1H, d), 3.87 (2H, q), 3.87 (3H, s), 1.39 (3H, t).
　本発明化合物５３：1H-NMR (CDCl3) δ: 8.79 (1H, d), 8.76 (1H, d), 8.31 (1H, d), 8.13 (1H, d), 7.14 (1H, s), 3.90 (2H, q), 3.87 (3H, s), 1.40 (3H, t).
　本発明化合物５４：1H-NMR (CDCl3) δ: 8.74 (1H, d), 8.66 (1H, d), 8.29 (1H, d), 7.97 (1H, d), 5.16 (2H, d), 4.67 (2H, s), 3.85 (3H, s), 3.84 (2H, q), 1.89 (3H, s), 1.36 (3H, t).
　本発明化合物５５：1H-NMR (CDCl3) δ: 8.77 (1H, d), 8.71 (1H, d), 8.30 (1H, d), 8.16 (1H, d), 3.88 (3H, s), 3.86 (2H, q), 1.63 (6H, s), 1.37 (3H, t).
　本発明化合物５６：1H-NMR (CDCl3) δ: 8.75 (1H, d), 8.69 (1H, d), 8.30 (1H, d), 8.01 (1H, d), 4.39-4.35 (2H, m), 3.89-3.80 (7H, m), 3.48 (3H, s), 1.36 (3H, t).
　本発明化合物５７： 1H-NMR (CDCl3) δ: 8.75 (1H, d), 8.71 (1H, d), 8.30 (1H, d), 8.01 (1H, d), 4.36 (2H, t), 3.87 (2H, q), 3.86 (3H, s), 1.85 (3H, t), 1.38 (3H, t).
Figure JPOXMLDOC01-appb-T000065
 The present compound 25: 1 H-NMR (CDCl 3 ) δ: 8.75 (1H), 8.70 (1H, d), 8.30 (1H, d), 7.94 (1H, d), 4.18 (2H), 3.90-3.83 ( 5H, m), 1.58-1.53 (2H, m), 1.38 (3H, t), 1.26-1.20 (2H, m).
The present compound 26: 1 H-NMR (CDCl 3 ) δ: 8.76 (1 H, d), 8. 74 (1 H, d), 8.31 (1 H, s), 8.04 (1 H, d), 4. 68 (2 H, t), 3.89 (2H, q), 3.87 (3H, s), 1.39 (3H, t).
The present compound 27: 1 H-NMR (CDCl 3 ) δ: 8.76 (1 H, d), 8. 73 (1 H, d), 8.31 (1 H, d), 8.04 (1 H, d), 5.26-5.15 (1 H, m ), 4.71-4.55 (2H, m), 3.91 (2H, q), 3.87 (3H, s), 1.39 (3H, t).
The present compound 28: 1 H-NMR (CDCl 3 ) δ: 8.76 ( 1 H, d), 8. 74 (1 H, d), 8. 30 (1 H, d), 8.04 (1 H, d), 4.71 (2 H, t), 3.90 (2H, q), 3.87 (3H, s), 1.39 (3H, t).
The present compound 29: 1 H-NMR (CDCl 3 ) δ: 8.75 (1 H, s), 8. 65 (1 H, d), 8. 29 ( 1 H, d), 7. 95 (1 H, d), 4. 27 (2 H, t), 3.85 (3H, s), 3.85 (2H, q), 2.41-2.39 (2H, m), 2.24-2.18 (2H, m), 1.37 (3H, t).
The present compound 30: 1 H-NMR (CDCl 3 ) δ: 8.76 ( 1 H, d), 8. 71 (1 H, d), 8. 30 (1 H, d), 8.03 (1 H, d), 4.94-4.91 (1 H, m ), 3.87 (3H, s), 3.86 (2H, q), 1.66 (3H, d), 1.38 (3H, t).
The present compound 31: 1 H-NMR (CDCl 3 ) δ: 8.76 (1H, d), 8.74 (1H, d), 8.30 (1H, d), 8.03 (1H, d), 4.62 (2H, q), 3.88 (2H, q), 3.86 (3H, s), 1.38 (3H, t).
The present compound 32: 1 H-NMR (CDCl 3 ) δ: 8.75 (1 H, d), 8. 67 (1 H, d), 8. 29 (1 H, d), 7. 97 (1 H, d), 4. 44 (2 H, t), 3.87 (2H, q), 3.85 (3H, s), 2.83-2.72 (2H, m), 1.38 (3H, t).
The present compound 33: 1 H-NMR (CDCl 3 ) δ: 8.75 ( 1 H, d), 8. 66 (1 H, d), 8. 29 (1 H, d), 7. 95 (1 H, d), 4.30-4. 26 (2 H, m ), 3.85 (2H, q), 3.85 (3H, s), 2.21-2.05 (1H, m), 1.76-1.67 (1H, m), 1.42-1.41 (1H, m), 1.37 (3H, t).
The present compound 34: 1 H-NMR (CDCl 3 ) δ: 8.75 (1H, d), 8.71 (1H, d), 8.30 (1H, d), 8.01 (1H, d), 6.20 (1H, tt), 4.44 (2H, td), 3.86 (2H, q), 3.86 (3H, s), 1.38 (3H, t).
The present compound 35: 1 H-NMR (CDCl 3 ) δ: 8.75 (1H, d), 8.63 (1H, d), 8.30 (1H, d), 7.94 (1H, d), 4.27 (2H, q), 3.86-3.81 (5H, m), 1.54 (3H, t), 1.36 (3H, t).
The present compound 36: 1 H-NMR (CDCl 3 ) δ: 8.74 (1H, d), 8.64 (1H, d), 8.30 (1H, d), 7.94 (1H, d), 4.16 (2H, t), 3.87-3.80 (5H, m), 1.9-1.87 (2H, m), 1.37 (3H, t), 1.11 (3H, t).
The present compound 37: 1 H-NMR (CDCl 3 ) δ: 8.74 (1H, dd), 8.59 (1H, d), 8.29 (1H, dd), 7.92 (1H, d), 4.84-4.78 (1H, m) ), 3.87-3.79 (5H, m), 1.47 (6H, d), 1.37 (3H, t).
The present compound 38: 1 H-NMR (CDCl 3 ) δ: 8.74 (1H, d), 8.63 (1H, d), 8.29 (1H, d), 7.94 (1H, d), 4.20 (2H, t), 3.84 (3H, s), 3.83 (2H, q), 1.92-1.85 (2H, m), 1.61-1.52 (2H, m), 1.37 (3H, t), 1.03 (3H, t).
The present compound 39: 1 H-NMR (CDCl 3 ) δ: 8.74 (1H, d), 8.63 (1H, d), 8.29 (1H, d), 7.93 (1H, d), 4.19 (2H, t), 3.84 (3H, s), 3.83 (2H, q), 1.94-1.87 (2H, m), 1.49-1.44 (4H, m), 1.37 (3H, t), 0.97 (3H, t).
The present compound 40: 1 H-NMR (CDCl 3 ) δ: 8.74 ( 1 H, d), 8. 59 (1 H, d), 8. 28 (1 H, d), 7. 92 (1 H, d), 4.59-4.56 (1 H, m ), 3.85 (3H, s), 3.83 (2H, q), 1.91-1.71 (2H, m), 1.42 (3H, d), 1.37 (3H, t), 1.05 (3H, t).
The present compound 41: 1 H-NMR (CDCl 3 ) δ: 8.74 (1H, d), 8.64 (1H, d), 8.29 (1H, d), 7.94 (1H, d), 3.95 (2H, d), 3.84 (3H, s), 3.82 (2H, q), 2.26-2.16 (1H, m), 1.37 (3H, t), 1.11 (6H, d).
The present compound 42: 1 H-NMR (CDCl 3 ) δ: 8.74 (1H, d), 8.65 (1H, d), 8.29 (1H, d), 7.94 (1H, d), 3.84 (3H, s), 3.84 (2H, q), 3.82 (2H, s), 1.38 (3H, t), 1.12 (9H, s).
Invention compound 43: 1 H-NMR (CDCl 3 ) δ: 8.74 ( 1 H, d), 8. 60 (1 H, d), 8. 28 (1 H, d), 7. 91 (1 H, d), 4.44-4. 38 (1 H, m ), 3.86 (3H, s), 3.83 (2H, q), 2.05-2.03 (1H, m), 1.38-1.36 (6H, m), 1.07-1.04 (6H, m).
The compound of the present invention 44: 1 H-NMR (CDCl 3 ) δ: 8.74 ( 1 H, d), 8. 60 (1 H, d), 8. 28 (1 H, d), 7. 92 (1 H, d), 4.44-4. 38 (1 H, m ), 3.86 (3H, s), 3.83 (2H, q), 1.80 (4H, dt), 1.37 (3H, t), 1.02 (6H, t).
Invention compound 45: 1 H-NMR (CDCl 3 ) δ: 8.75 (1H, d), 8.64 (1H, d), 8.29 (1H, d), 8.08 (1H, d), 3.87 (3H, s), 3.82 (2H, q), 1.54 (9H, s), 1.36 (3H, t).
The present compound 46: 1 H-NMR (CDCl 3 ) δ: 8.75 (1 H, d), 8. 71 (1 H, d), 8. 29 (1 H, d), 8.09 (1 H, d), 4.95 (2 H, s), 3.86 (3H, s), 3.83 (2H, q), 2.67 (1H, s), 1.38 (3H, t).
Invention compound 47: 1 H-NMR (CDCl 3 ) δ: 8.74 (1 H, s), 8.62 (1 H, s), 8. 28 (1 H, s), 7. 95 (1 H, s), 5. 96-5. 87 (1 H, m ), 5.42-5.33 (2H, m), 5.05-5.02 (1H, m), 3.88 (2H, q), 3.85 (3H, s), 1.58 (3H, d), 1.35 (3H, t).
The present compound 48: 1 H-NMR (CDCl 3 ) δ: 8.72 ( 1 H, s), 8. 64 (1 H, s), 8. 27 (1 H, s), 7. 96 (1 H, s), 4.37-4. 30 (2 H, m ), 3.84 (2H, q), 3.82 (3H, s), 2.79-2.79 (2H, m), 2.11-2.08 (1H, m), 1.35 (3H, t).
Invention compound 49: 1 H-NMR (CDCl 3 ) δ: 8.74 (1H, d), 8.65 (1H, d), 8.28 (1H, d), 7.93 (1H, d), 4.05 (2H, d), 3.84 (3H, s), 3.83 (2H, m), 1.35-1.39 (4H, m), 0.78-0.74 (2H, m), 0.46-0.45 (2H, m).
The present compound 50: 1 H-NMR (CDCl 3 ) δ: 8.74 (1H, d), 8.66 (1H, d), 8.29 (1H, d), 7.96 (1H, d), 6.10-6.06 (1H, m) ), 5.52-5.45 (2H, m), 4.79-4.78 (2H, m), 3.88-3.82 (5H, m), 1.36 (3H, t).
Invention compound 51: 1 H-NMR (CDCl 3 ) δ: 8.74 ( 1 H, d), 8. 64 (1 H, d), 8. 29 (1 H, d), 7. 95 (1 H, d), 5. 96-5. 89 (1 H, m ), 5.27-5.19 (2H, m), 4.25 (2H, t), 3.84 (3H, s), 3.83 (2H, q), 2.69-2.64 (2H, m), 1.37 (3H, t).
The present compound 52: 1 H-NMR (CDCl 3 ) δ: 8.76 (1H, d), 8.74 (1H, d), 8.30 (1H, d), 8.10 (1H, d), 7.02 (1H, d), 6.41 (1H, d), 3.87 (2H, q), 3.87 (3H, s), 1.39 (3H, t).
Invention compound 53: 1 H-NMR (CDCl 3 ) δ: 8.79 (1 H, d), 8. 76 (1 H, d), 8.31 (1 H, d), 8.13 (1 H, d), 7.14 (1 H, s), 3.90 (2H, q), 3.87 (3H, s), 1.40 (3H, t).
Invention compound 54: 1 H-NMR (CDCl 3 ) δ: 8.74 (1 H, d), 8. 66 ( 1 H, d), 8. 29 (1 H, d), 7. 97 (1 H, d), 5. 16 (2 H, d), 4.67 (2H, s), 3.85 (3H, s), 3.84 (2H, q), 1.89 (3H, s), 1.36 (3H, t).
The present compound 55: 1 H-NMR (CDCl 3 ) δ: 8.77 (1H, d), 8.71 (1H, d), 8.30 (1H, d), 8.16 (1H, d), 3.88 (3H, s), 3.86 (2H, q), 1.63 (6H, s), 1.37 (3H, t).
The present compound 56: 1 H-NMR (CDCl 3 ) δ: 8.75 ( 1 H, d), 8. 69 (1 H, d), 8. 30 (1 H, d), 8.01 (1 H, d), 4. 39-4. 35 (2 H, m ), 3.89-3.80 (7H, m), 3.48 (3H, s), 1.36 (3H, t).
The present compound 57: 1 H-NMR (CDCl 3 ) δ: 8.75 ( 1 H, d), 8. 71 (1 H, d), 8. 30 (1 H, d), 8.01 (1 H, d), 4. 36 (2 H, t), 3.87 (2H, q), 3.86 (3H, s), 1.85 (3H, t), 1.38 (3H, t).
参考製造例９
　２－［５－ブロモ－３－（エタンスルホニル）ピリジン－２－イル］－３－メチル－６－（トリフルオロメチル）－３Ｈ－イミダゾ［４，５－ｂ］ピリジン９．０ｇ、ビス（ピナコラト）ジボロン５．６ｇ、［１，１’－ビス（ジフェニルホスフィノ）フェロセン］パラジウム（ＩＩ）ジクロリド ジクロロメタン付加物０．４９ｇ、酢酸カリウム５．９ｇ及びＤＭＳＯ８０ｍＬの混合物を、窒素雰囲気下９０℃で１０時間撹拌した。得られた混合物に室温で水を加え、クロロホルムで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮し、次式で示される中間体１１を８．１ｇ得た。
Figure JPOXMLDOC01-appb-C000066
 中間体１１：1H-NMR (CDCl3) δ: 9.27 (1H, d), 8.87 (1H, d), 8.76 (1H, d), 8.31 (1H, d), 3.87 (3H, s), 3.82 (2H, q), 1.42 (12H, s), 1.38 (3H, t). Reference Production Example 9
2- [5-bromo-3- (ethanesulfonyl) pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine 9.0 g, bis (pinacolato) ) A mixture of 5.6 g of diboron, 0.49 g of [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct, 5.9 g of potassium acetate and 80 mL of DMSO at 90 ° C. under a nitrogen atmosphere. Stir for hours. To the resulting mixture was added water at room temperature, and extracted with chloroform. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 8.1 g of Intermediate 11 represented by the following formula.
Figure JPOXMLDOC01-appb-C000066
 Intermediate 11: 1 H-NMR (CDCl 3 ) δ: 9.27 (1H, d), 8.87 (1H, d), 8.76 (1H, d), 8.31 (1H, d), 3.87 (3H, s), 3.82 (2H, q), 1.42 (12H, s), 1.38 (3H, t).
参考製造例１０
　０．９９ｇの中間体１１、酢酸ナトリウム１．２ｇ、ＴＨＦ８ｍＬ及び水４ｍＬの混合物に、３０％過酸化水素水１．１ｍＬを加え、０℃で６時間撹拌した。得られた混合物に、飽和チオ硫酸ナトリウム３０ｍＬを加え、１時間撹拌した。得られた混合物に飽和重曹水を加え、クロロホルムで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、次式で示される中間体１２を０．４６ｇ得た。
Figure JPOXMLDOC01-appb-C000067
 中間体１２：1H-NMR (CDCl3) δ: 8.78-8.76 (1H, m), 8.49 (1H, d), 8.33-8.31 (1H, m), 7.87 (1H, d), 3.84 (3H, s), 3.70 (2H, q), 1.36 (3H, t). Reference Production Example 10
To a mixture of 0.99 g of Intermediate 11, 1.2 g of sodium acetate, 8 mL of THF and 4 mL of water, 1.1 mL of 30% hydrogen peroxide water was added and stirred at 0 ° C. for 6 hours. To the resulting mixture, 30 mL of saturated sodium thiosulfate was added and stirred for 1 hour. To the resulting mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.46 g of Intermediate 12 represented by the following formula.
Figure JPOXMLDOC01-appb-C000067
 Intermediate 12: 1 H-NMR (CDCl 3 ) δ: 8.78-8.76 (1H, m), 8.49 (1H, d), 8.33-8. 31 (1H, m), 7.87 (1H, d), 3.84 (3H, 3) s), 3.70 (2H, q), 1.36 (3H, t).
製造例９
　１５０ｍｇの中間体１２及びクロロホルム２ｍＬの混合物に、氷冷下でジイソプロピルエチルアミン２５０μＬ及びメトキシメチルクロリド１０５μＬを順次加えた。得られた混合物を、室温に昇温後８時間撹拌した。得られた混合物に水を加え、クロロホルムで抽出した。得られた有機層を、飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルクロマトグラフィー（ヘキサン：酢酸エチル＝２：１）に付し、次式で示される本発明化合物５８を１５２ｍｇ得た。
Figure JPOXMLDOC01-appb-C000068
 本発明化合物５８：1H-NMR (CDCl3) δ: 8.76-8.73 (2H, m), 8.29 (1H, d), 8.14 (1H, d), 5.39 (2H, s), 3.86 (3H, s), 3.82 (2H, q), 3.56 (3H, s), 1.37 (3H, t). Production Example 9
To a mixture of 150 mg of Intermediate 12 and 2 mL of chloroform, 250 μL of diisopropylethylamine and 105 μL of methoxymethyl chloride were sequentially added under ice-cooling. The resulting mixture was stirred for 8 hours after warming to room temperature. To the resulting mixture was added water, and extracted with chloroform. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography (hexane: ethyl acetate = 2: 1) to obtain 152 mg of the present compound 58 represented by the following formula.
Figure JPOXMLDOC01-appb-C000068
 Invention compound 58: 1 H-NMR (CDCl 3 ) δ: 8.76-8.73 (2H, m), 8.29 (1 H, d), 8.14 (1 H, d), 5. 39 (2 H, s), 3. 86 ( 3 H, s) ), 3.82 (2H, q), 3.56 (3H, s), 1.37 (3H, t).
参考製造例１１
　２－［５－フルオロ－３－（エタンスルホニル）ピリジン－２－イル］－３－メチル－６－（トリフルオロメチル）－３Ｈ－イミダゾ［４，５－ｂ］ピリジン４．０ｇ及びクロロホルム５０ｍＬの混合物に、６０℃でｍＣＰＢＡ２３．７ｇを加え、８時間撹拌した。得られた混合物に飽和チオ硫酸ナトリウム水溶液と飽和重曹水を加え、クロロホルムで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、次式で示される中間体１３を１．８３ｇ得た。
Figure JPOXMLDOC01-appb-C000069
 中間体１３：1H-NMR (CDCl3) δ: 8.88 (1H, d), 8.48 (1H, d), 8.26 (1H, d), 7.92 (1H, d), 4.28 (3H, s), 3.74 (2H, q), 1.38 (3H, t). Reference Production Example 11
2- [5-Fluoro-3- (ethanesulfonyl) pyridin-2-yl] -3-methyl-6- (trifluoromethyl) -3H-imidazo [4,5-b] pyridine 4.0 g and 50 mL chloroform The mixture was added with 23.7 g of mCPBA at 60 ° C. and stirred for 8 hours. To the resulting mixture were added saturated aqueous sodium thiosulfate solution and saturated aqueous sodium bicarbonate solution, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 1.83 g of Intermediate 13 represented by the following formula.
Figure JPOXMLDOC01-appb-C000069
 Intermediate 13: 1 H-NMR (CDCl 3 ) δ: 8.88 (1 H, d), 8. 48 (1 H, d), 8. 26 (1 H, d), 7. 92 (1 H, d), 4. 28 (3 H, s), 3.74 (2H, q), 1.38 (3H, t).
製造例１０
　２００ｍｇの中間体１３、ＤＭＦ１ｍＬ及び２－プロパノール１ｍＬの混合物に、氷冷下で水素化ナトリウム（６０％、油性）２０ｍｇを加えた。得られた混合物を、室温に昇温後１時間撹拌した。得られた混合物に水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、次式で示される本発明化合物５９を１６３ｍｇ得た。
Figure JPOXMLDOC01-appb-C000070
 本発明化合物５９：1H-NMR (CDCl3) δ: 8.59 (1H, d), 8.45 (1H, d), 7.90 (1H, d), 7.88 (1H, d), 4.83-4.77 (1H, m), 4.26 (3H, s), 3.70 (2H, q), 1.47 (6H, d), 1.36 (3H, t). Production Example 10
To a mixture of 200 mg of Intermediate 13, 1 mL of DMF and 1 mL of 2-propanol was added 20 mg of sodium hydride (60%, oily) under ice-cooling. The resulting mixture was stirred for 1 hour after warming to room temperature. To the resulting mixture was added water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 163 mg of the present compound 59 represented by the following formula.
Figure JPOXMLDOC01-appb-C000070
 Invention compound 59: 1 H-NMR (CDCl 3 ) δ: 8.59 ( 1 H, d), 8. 45 (1 H, d), 7. 90 (1 H, d), 7. 88 (1 H, d), 4.83-4. 77 (1 H, m ), 4.26 (3H, s), 3.70 (2H, q), 1.47 (6H, d), 1.36 (3H, t).
製造例１１
　製造例１０に準じて製造した化合物及びその物性値を以下に示す。
　式（Ａ－６）：
Figure JPOXMLDOC01-appb-C000071
 で示される化合物において、Ｒ2が［表９］に記載のいずれかの化合物。 Production Example 11
The compounds produced according to Production Example 10 and the physical properties thereof are shown below.
Formula (A-6):
Figure JPOXMLDOC01-appb-C000071
 In the compounds represented by the above, R 2 is any compound described in [Table 9].
Figure JPOXMLDOC01-appb-T000072
 　本発明化合物６０：1H-NMR (CDCl3) δ: 8.63 (1H, d), 8.45 (1H, d), 7.90 (2H, dd), 4.28 (2H, q), 4.25 (3H, s), 3.70 (2H, q), 1.54 (3H, t), 1.35 (3H, t).
　本発明化合物６１：1H-NMR (CDCl3) δ: 8.64 (1H, d), 8.45 (1H, d), 7.91 (1H, d), 7.91 (1H, d), 4.25 (3H, s), 4.16 (2H, t), 3.70 (2H, q), 1.95-1.92 (2H, m), 1.36 (3H, t), 1.12 (3H, t).
　本発明化合物６２：1H-NMR (CDCl3) δ: 8.72 (1H, s), 8.47 (1H, s), 8.13 (1H, s), 7.92 (1H, s), 4.29 (3H, s), 3.72 (2H, q), 1.64 (6H, s), 1.36 (3H, t).
Figure JPOXMLDOC01-appb-T000072
 The present compound 60: 1 H-NMR (CDCl 3 ) δ: 8.63 (1H, d), 8.45 (1H, d), 7.90 (2H, dd), 4.28 (2H, q), 4.25 (3H, s), 3.70 (2H, q), 1.54 (3H, t), 1.35 (3H, t).
The present compound 61: 1 H-NMR (CDCl 3 ) δ: 8.64 (1 H, d), 8. 45 (1 H, d), 7. 91 (1 H, d), 7. 91 (1 H, d), 4. 25 (3 H, s), 4.16 (2H, t), 3.70 (2H, q), 1.95-1.92 (2H, m), 1.36 (3H, t), 1.12 (3H, t).
The present compound 62: 1 H-NMR (CDCl 3 ) δ: 8.72 (1 H, s), 8. 47 (1 H, s), 8.13 (1 H, s), 7. 92 (1 H, s), 4. 29 (3 H, s), 3.72 (2H, q), 1.64 (6H, s), 1.36 (3H, t).
製造例１２
　１．５ｇの中間体４－３、ＤＭＦ１００μＬ及びクロロホルム１０ｍＬの混合物に室温で塩化オキサリル１ｍＬを加え、室温で８時間撹拌した。得られた混合物を減圧下で濃縮し、得られた残渣にアセトニトリル１０ｍＬを加えた。得られた混合物に２－アミノ－４－（トリフルオロメタンスルフィニル）フェノール１．１８ｇを加え、室温で８時間撹拌した。得られた混合物に水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣に、ビス（２－メトキシエチル）＝アゾジカルボキシラート１．４８ｇ及びＴＨＦ３０ｍＬを加えた。得られた混合物に室温でトリフェニルホスフィン１．６６ｇを加え、６０℃で１時間撹拌した。得られた混合物を室温にし、水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルクロマトグラフィーに付し、本発明化合物２１を８６０ｍｇ得た。 Production Example 12
1 mL of oxalyl chloride was added to a mixture of 1.5 g of Intermediate 4-3, 100 μL of DMF and 10 mL of chloroform at room temperature, and stirred at room temperature for 8 hours. The resulting mixture was concentrated under reduced pressure and 10 mL of acetonitrile was added to the resulting residue. To the resulting mixture was added 1.18 g of 2-amino-4- (trifluoromethanesulfinyl) phenol, and the mixture was stirred at room temperature for 8 hours. To the resulting mixture was added water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the resulting residue was added 1.48 g of bis (2-methoxyethyl) = azodicarboxylate and 30 mL of THF. To the resulting mixture was added 1.66 g of triphenylphosphine at room temperature and stirred at 60 ° C. for 1 hour. The resulting mixture was brought to room temperature, water was added and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 860 mg of the present compound 21.
　次に本発明化合物の製剤例を示す。なお、部は重量部を表す。 Next, formulation examples of the compound of the present invention are shown. In addition, a part represents a weight part.
製剤例１
　本発明化合物１～６５のいずれか１種１０部を、キシレン３５部とＤＭＦ３５部との混合物に混合し、そこにポリオキシエチレンスチリルフェニルエーテル１４部及びドデシルベンゼンスルホン酸カルシウム６部を加え、混合して製剤を得る。 Formulation example 1
10 parts of any one of the compounds 1 to 65 of the present invention is mixed in a mixture of 35 parts of xylene and 35 parts of DMF, and 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzene sulfonate are added thereto and mixed To obtain a formulation.
製剤例２
　ラウリル硫酸ナトリウム４部、リグニンスルホン酸カルシウム２部、湿式シリカ２０部及び珪藻土５４部を混合し、更に本発明化合物１～６５のいずれか１種２０部を加え、混合して製剤を得る。 Formulation example 2
4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of wet silica and 54 parts of diatomaceous earth are mixed, and further 20 parts of any one of the compounds of the present invention 1 to 65 is added and mixed to obtain a preparation.
製剤例３
　本発明化合物１～６５のいずれか１種２部に、湿式シリカ１部、リグニンスルホン酸カルシウム２部、ベントナイト３０部及びカオリンクレー６５部を加え混合する。ついで、この混合物に適当量の水を加え、さらに撹拌し、造粒機で造粒し、通風乾燥して製剤を得る。 Formulation example 3
1 part of wet silica, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are added to 2 parts of any one compound of the present invention 1 to 65 and mixed. Then, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated with a granulator and blow-dried to obtain a preparation.
製剤例４
　本発明化合物１～６５のいずれか１種１部を適当量のアセトンに混合し、これに湿式シリカ５部、酸性りん酸イソプロピル０．３部及びカオリンクレー９３．７部を加え、充分撹拌混合し、アセトンを蒸発除去して製剤を得る。 Formulation example 4
1 part of any one of the compounds 1 to 65 of the present invention is mixed with an appropriate amount of acetone, 5 parts of wet silica, 0.3 parts of isopropyl acid phosphate and 93.7 parts of kaolin clay are added thereto and thoroughly mixed The acetone is evaporated off to obtain the preparation.
製剤例５
　ポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩及び湿式シリカの混合物（重量比１：１）３５部と、本発明化合物１～６５のいずれか１種２０部と、水４５部とを十分に混合し、製剤を得る。 Formulation example 5
A formulation is prepared by thoroughly mixing 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and wet silica (weight ratio 1: 1), 20 parts of any one of the compounds of the present invention 1 to 65, and 45 parts of water Get
製剤例６
　本発明化合物１～６５のいずれか１種０．１部をキシレン５部及びトリクロロエタン５部の混合物に混合し、これをケロシン８９．９部に混合して製剤を得る。 Formulation Example 6
0.1 part of any one of the compounds 1 to 65 of the present invention is mixed with a mixture of 5 parts of xylene and 5 parts of trichloroethane, and this is mixed with 89.9 parts of kerosene to obtain a preparation.
製剤例７
　本発明化合物１～６５のいずれか１種１０ｍｇをアセトン０．５ｍＬに混合し、この溶液を、動物用固形飼料粉末（飼育繁殖用固形飼料粉末ＣＥ－２、日本クレア株式会社商品）５ｇに滴下し、均一に混合する。ついでアセトンを蒸発乾燥させて毒餌剤を得る。 Formulation example 7
10 mg of any one of the compounds 1 to 65 of the present invention is mixed with 0.5 mL of acetone, and this solution is added dropwise to 5 g of solid feed powder for animals (solid feed powder for rearing and breeding CE-2 manufactured by CLEA Japan, Inc.) And mix uniformly. The acetone is then evaporated to dryness to obtain a toxic bait.
製剤例８
　本発明化合物１～６５のいずれか１種０．１部、ネオチオゾール（中央化成株式会社製）４９．９部をエアゾール缶に入れ、エアゾールバルブを装着した後、ジメチルエーテル２５部、ＬＰＧ２５部を充填し振とうを加え、アクチュエータを装着することにより油剤エアゾールを得る。 Formulation Example 8
0.1 parts of any one of the compounds 1 to 65 of the present invention and 49.9 parts of neothiozole (manufactured by Chuo Kasei Co., Ltd.) are put into an aerosol can, fitted with an aerosol valve, and filled with 25 parts of dimethyl ether and 25 parts of LPG. Shake is applied and the actuator is mounted to obtain an oil aerosol.
製剤例９
　本発明化合物１～６５のいずれか１種０．６部、２，６－ジ－ｔｅｒｔ－ブチル－４－メチルフェノール０．０１部、キシレン５部、ケロシン３．３９部及び乳化剤｛レオドールＭＯ－６０（花王株式会社製）｝１部を混合したものと、蒸留水５０部とをエアゾール容器に充填し、バルブを装着した後、該バルブを通じて噴射剤（ＬＰＧ）４０部を加圧充填して水性エアゾールを得る。 Formulation Example 9
0.6 parts of any one of the compounds 1 to 65 of the present invention, 0.01 parts of 2,6-di-tert-butyl-4-methylphenol, 5 parts of xylene, 3.39 parts of kerosene and an emulsifier {Leodol MO- 60 parts (made by Kao Corporation) and 50 parts of distilled water are filled in an aerosol container, and after mounting a valve, 40 parts of propellant (LPG) is pressure-filled through the valve. Obtain an aqueous aerosol.
製剤例１０
　本発明化合物１～６５のいずれか１種０．１ｇを、プロピレングリコール２ｍＬに混合し、４．０ｃｍ×４．０ｃｍ、厚さ１．２ｃｍのセラミック板に含浸させて、加熱式くん煙剤を得る。 Formulation Example 10
0.1 g of any one of the compounds 1 to 65 of the present invention is mixed with 2 mL of propylene glycol and impregnated into a 4.0 cm × 4.0 cm, 1.2 cm thick ceramic plate, and a heating smoke agent is added. obtain.
製剤例１１
　本発明化合物１～６５のいずれか１種５部とエチレン－メタクリル酸メチル共重合体（共重合体の総重量に対するメタクリル酸メチルの割合：１０重量％、アクリフト（登録商標）ＷＤ３０１、住友化学製）９５部を密閉式加圧ニーダー（森山製作所製）で溶融混練し、得られた混練物を押出し成型機から成型ダイスを介して押出し、長さ１５ｃｍ、直径３ｍｍの棒状成型体を得る。 Formulation example 11
5 parts of any one of the compounds 1 to 65 of the present invention and ethylene-methyl methacrylate copolymer (the ratio of methyl methacrylate to the total weight of the copolymer: 10% by weight, Aclift (registered trademark) WD 301, manufactured by Sumitomo Chemical Co., Ltd. 95 parts are melt-kneaded with a closed type pressure kneader (manufactured by Moriyama Seisakusho), and the obtained kneaded product is extruded from an extrusion molding machine through a molding die to obtain a rod-shaped molding having a length of 15 cm and a diameter of 3 mm.
製剤例１２
　本発明化合物１～６５のいずれか１種５部及び軟質塩化ビニル樹脂９５部を密閉式加圧ニーダー（森山製作所製）で溶融混練し、得られた混練物を押出し成型機から成型ダイスを介して押出し、長さ１５ｃｍ、直径３ｍｍの棒状成型体を得る。 Formulation example 12
5 parts of any one of the compounds 1 to 65 of the present invention and 95 parts of a soft vinyl chloride resin are melt-kneaded with a closed-type pressure kneader (manufactured by Moriyama Seisakusho), and the obtained kneaded product is extruded through an extrusion molding machine The mixture is extruded to obtain a rod-shaped molding having a length of 15 cm and a diameter of 3 mm.
製剤例１３
　本発明化合物１～６５のいずれか１種１００ｍｇ、ラクトース６８．７５ｍｇ、トウモロコシデンプン２３７．５ｍｇ、微結晶性セルロース４３．７５ｍｇ、ポリビニルピロリドン１８．７５ｍｇ、ナトリウムカルボキシメチルデンプン２８．７５ｍｇ、及びステアリン酸マグネシウム２．５ｍｇを混合し、得られた混合物を適切な大きさに圧縮して、錠剤を得る。 Formulation example 13
100 mg of any one of the compounds 1 to 65 of the present invention, 68.75 mg of lactose, 237.5 mg of corn starch, 43.75 mg of microcrystalline cellulose, 18.75 mg of polyvinylpyrrolidone, 28.75 mg of sodium carboxymethyl starch, and magnesium stearate 2.5 mg are mixed and the resulting mixture is compressed to a suitable size to obtain tablets.
製剤例１４
　本発明化合物１～６５のいずれか１種２５ｍｇ、ラクトース６０ｍｇ、トウモロコシデンプン２５ｍｇ、カルメロースカルシウム６ｍｇ、及び５％ヒドロキシプロピルメチルセルロース適量を混合し、得られた混合物をハードシェルゼラチンカプセル又はヒドロキシプロピルメチルセルロースカプセルに充填し、カプセル剤を得る。 Formulation example 14
25 mg of any one of the compounds 1 to 65 of the present invention, 60 mg of lactose, 25 mg of corn starch, 6 mg of carmellose calcium, and 5% hydroxypropyl methylcellulose, and mixed appropriately to obtain hard shell gelatin capsule or hydroxypropyl methylcellulose capsule To give capsules.
製剤例１５
　本発明化合物１～６５のいずれか１種１００ｍｇ、フマル酸５００ｍｇ、塩化ナトリウム２,０００ｍｇ、メチルパラベン１５０ｍｇ、プロピルパラベン５０ｍｇ、顆粒糖２５,０００ｍｇ、ソルビトール（７０％溶液）１３,０００ｍｇ、Ｖｅｅｇｕｍ（登録商標）　Ｋ（Ｖａｎｄｅｒｂｉｌｔ　Ｃｏ．）１００ｍｇ、香料３５ｍｇ、及び着色料５００ｍｇに、最終容量が１００ｍｌとなるよう蒸留水を加え、混合して、経口投与用サスペンジョンを得る。 Formulation example 15
100 mg of any one of the compounds 1 to 65 of the present invention, 500 mg of fumaric acid, 2,000 mg of sodium chloride, 150 mg of methylparaben, 50 mg of propylparaben, 25,000 mg of granular sugar, 13,000 mg of sorbitol (70% solution), Veegum (registered trademark) To 100 mg of K (Vanderbilt Co.), 35 mg of perfume and 500 mg of coloring matter, distilled water is added to a final volume of 100 ml and mixed to obtain a suspension for oral administration.
製剤例１６
　本発明化合物１～６５のいずれか１種５重量％を、乳化剤　５重量％、ベンジルアルコール３重量％、及びプロピレングリコール３０重量％に混合し、この溶液のｐＨが６．０～６．５となるようにリン酸塩緩衝液を加えた後、残部として水を加えて、経口投与用液剤を得る。 Formulation example 16
5% by weight of any one of the compounds 1 to 65 of the present invention is mixed with 5% by weight of an emulsifier, 3% by weight of benzyl alcohol and 30% by weight of propylene glycol, and the pH of this solution is 6.0 to 6.5. After adding the phosphate buffer solution as it becomes, water is added as the balance to obtain a solution for oral administration.
製剤例１７
　分留ヤシ油５７重量％及び３重量％のポリソルベート８５中にジステアリン酸アルミニウム５重量％を加え、加熱により分散させる。これを室温に冷却し、その油状ビヒクル中にサッカリン２５重量％を分散させる。これに本発明化合物１～６５のいずれか１種１０重量％を配分し、経口投与用ペースト状製剤を得る。 Formulation example 17
5% by weight of aluminum distearate is added to 57% by weight of fractionated palm oil and 3% by weight of polysorbate 85 and dispersed by heating. It is cooled to room temperature and 25% by weight of saccharin is dispersed in the oily vehicle. To this, 10% by weight of any one of the compounds of the present invention 1 to 65 is distributed to obtain a paste-form preparation for oral administration.
製剤例１８
　本発明化合物１～６５のいずれか１種５重量％を石灰石粉９５重量％と混合し、湿潤顆粒形成法を使用して経口投与用粒剤を得る。 Formulation example 18
5% by weight of any one of the compounds 1 to 65 of the present invention is mixed with 95% by weight of limestone powder to obtain granules for oral administration using a wet granulation method.
製剤例１９
　本発明化合物１～６５のいずれか１種５部をジエチレングリコールモノエチルエーテル８０部に混合し、これに炭酸プロピレン１５部を混合して、スポットオン液剤を得る。 Formulation example 19
Five parts of any one of the compounds 1 to 65 of the present invention is mixed with 80 parts of diethylene glycol monoethyl ether, and 15 parts of propylene carbonate is mixed therewith to obtain a spot-on solution.
製剤例２０
　本発明化合物１～６５のいずれか１種１０部をジエチレングリコールモノエチルエーテル７０部に混合し、これに２－オクチルドデカノール２０部を混合して、ポアオン液剤を得る。 Formulation example 20
Ten parts of any one of the compounds 1 to 65 of the present invention is mixed with 70 parts of diethylene glycol monoethyl ether, and 20 parts of 2-octyldodecanol is mixed therewith to obtain a pour-on liquid agent.
製剤例２１
　本発明化合物１～６５のいずれか１種０．５部に、ニッコール（登録商標）ＴＥＡＬＳ－４２（日光ケミカルズ・ラウリル硫酸トリエタノールアミンの４２％水溶液）６０部、及びプロピレングリコール２０部を添加し、均一溶液になるまで充分撹拌混合した後、水１９．５部を加えてさらに充分撹拌混合し、均一溶液のシャンプー剤を得る。 Formulation example 21
To 0.5 part of any one of the compounds 1 to 65 of the present invention, 60 parts of NIKKOL® TEALS-42 (A 42% aqueous solution of Nikko Chemicals' triethanolamine lauryl sulfate triethanolamine) and 20 parts of propylene glycol are added After thoroughly mixing with stirring to obtain a uniform solution, 19.5 parts of water is added and the mixture is further sufficiently stirred and mixed to obtain a shampoo solution of a uniform solution.
製剤例２２
　本発明化合物１～６５のいずれか１種０．１５重量％、動物飼料９５重量％、並びに、第２リン酸カルシウム、珪藻土、Ａｅｒｏｓｉｌ（登録商標）、及びカーボネート（又はチョーク）からなる混合物４．８５重量％を十分撹拌混合し、動物用飼料プレミックスを得る。 Formulation example 22
0.15% by weight of any one of the compounds 1 to 65 of the present invention, 95% by weight of animal feed, and 4.85% by weight of a mixture consisting of calcium phosphate dibasic, diatomaceous earth, Aerosil (registered trademark), and carbonate (or chalk) Mix thoroughly to obtain an animal feed premix.
製剤例２３
　本発明化合物１～６５のいずれか１種７．２ｇ、及びホスコ（登録商標）Ｓ－５５（丸石製薬株式会社製）９２．８ｇを１００℃で混合し、坐剤形に注いで、冷却固化して、坐剤を得る。 Formulation example 23
7.2 g of any one of the compounds 1 to 65 of the present invention and 92.8 g of FOSCO S-55 (manufactured by Maruishi Pharmaceutical Co., Ltd.) are mixed at 100 ° C., poured into a suppository form, and cooled and solidified And get a suppository.
　次に、本発明化合物の有害節足動物に対する効力を試験例により示す。下記試験例において、試験は２５℃で行った。 Next, the efficacy of the compounds of the present invention against harmful arthropods is shown by test examples. In the following test examples, the test was performed at 25 ° C.
試験例１
　供試化合物を製剤例５に記載の方法に準じて製剤とし、これにシンダイン（登録商標）０．０３容量％含有する水を加え、供試化合物を所定濃度含有する希釈液を調製する。
　容器に植えたキュウリ（Cucumis sativus）苗（第２本葉展開期）にワタアブラムシ（全ステージ）約３０頭を接種する。１日後、この苗に該希釈液を１０ｍＬ／苗の割合で散布する。更に５日後、生存虫数を調査し、以下の式により防除価を求める。
　　　防除価（％）＝｛１－（Ｃｂ×Ｔａｉ）／（Ｃａｉ×Ｔｂ）｝×１００
なお、式中の文字は以下の意味を表す。
　　　Ｃｂ：無処理区の供試虫数
　　　Ｃａｉ：無処理区の調査時の生存虫数
　　　Ｔｂ：処理区の供試虫数
　　　Ｔａｉ：処理区の調査時の生存虫数
　ここで無処理区とは、供試化合物を使用しないこと以外は処理区と同じ操作をする区を意味する。 Test Example 1
A test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Syndyne (registered trademark) is added thereto to prepare a diluted solution containing a predetermined concentration of the test compound.
About 30 cotton aphids (all stages) are inoculated to cucumber (Cucumis sativus) seedlings (the second true leaf development stage) planted in a container. One day later, the seedlings are sprayed with the diluted solution at a rate of 10 mL / seedling. After 5 days, the number of surviving insects is examined, and the control value is determined by the following equation.
Control value (%) = {1- (Cb × Tai) / (Cai × Tb)} × 100
The letters in the formula have the following meanings.
Cb: Number of tested insects in untreated area Cai: Number of surviving insects in survey in untreated area Tb: Number of tested insects in treated zone Tai: Number of surviving insects in survey in treated area Here, untreated group means It means a zone that performs the same operation as the treatment zone except that the test compound is not used.
　所定濃度を５００ｐｐｍとし、下記の本発明化合物を供試化合物として用いて試験例１に従って試験を行った結果、下記の本発明化合物はいずれも防除価９０％以上を示した。
本発明化合物：５，６，７，８，９，１０、１１，１２，１３，１５，１６，１７，１８，１９，２０，２１，２２，２３，２４，２５，２６，２７，２９，３０，３１，３２，３３，３４，３５，３６，３７，３８，３９，４０，４１，４２，４３，４４，４５，４７，４８，４９，５０，５１，５４，５５，５６，５７，５９，６０，６１，６２，６３，６４及び６５ As a result of conducting a test according to Test example 1 by setting the predetermined concentration to 500 ppm and using the following compound of the present invention as a test compound, all of the following compounds of the present invention showed a control value of 90% or more.
The compounds of the present invention: 5, 6, 7, 8, 9, 10, 11, 12, 13, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 24, 26, 27, 29, 30, 31, 32, 23, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 45, 47, 48, 49, 50, 51, 54, 55, 56, 57, 59, 60, 61, 62, 63, 64 and 65
　所定濃度を２００ｐｐｍとし、下記の本発明化合物を供試化合物として用いて試験例１に従って試験を行った結果、下記の本発明化合物はいずれも防除価９０％以上を示した。
本発明化合物：７，８，９，１１，１２，１３，１５，１６，１７，１８，２０，２１，２２，２３，２４，２５，２６，２７，２９，３０，３１，３２，３３，３４，３５，３６，３７，３８，３９，４０，４１，４２，４３，４４，４５，４７，４８，４９，５０，５１，５４，５５，５６，５７，５９，６０，６１及び６２ The test was conducted according to Test Example 1 using the present invention compound described below as a test compound with a predetermined concentration of 200 ppm. As a result, all the present invention compounds described below exhibited a control value of 90% or more.
The compounds of the present invention: 7, 8, 9, 11, 12, 13, 13, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 29, 30, 31, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 49, 50, 51, 54, 55, 56, 57, 59, 60, 61 and 62
試験例２
　供試化合物を製剤例５に記載の方法に準じて製剤とし、これに水を加え、供試化合物を所定濃度含有する希釈液を調製する。
　容器に植えたキュウリ苗（第２本葉展開期）に該希釈液を５ｍＬ／苗の割合で株元灌注する。７日後、この苗の葉面にワタアブラムシ（全ステージ）約３０頭を接種する。更に６日後、生存虫数を調査し、以下の式により防除価を求める。
　　　防除価（％）＝｛１－（Ｃｂ×Ｔａｉ）／（Ｃａｉ×Ｔｂ）｝×１００
なお、式中の文字は以下の意味を表す。
　　　Ｃｂ：無処理区の供試虫数
　　　Ｃａｉ：無処理区の調査時の生存虫数
　　　Ｔｂ：処理区の供試虫数
　　　Ｔａｉ：処理区の調査時の生存虫数
　ここで無処理区とは、供試化合物を使用しないこと以外は処理区と同じ操作をする区を意味する。 Test example 2
A test compound is formulated according to the method described in Formulation Example 5, water is added thereto, and a diluted solution containing the test compound at a predetermined concentration is prepared.
The diluted solution is irrigated at the rate of 5 mL / seedling to cucumber seedlings (the second true leaf development stage) planted in a container. Seven days later, about 30 cotton aphids (all stages) are inoculated on the leaf surface of this seedling. After six more days, the number of surviving insects is examined, and the control value is determined by the following equation.
Control value (%) = {1- (Cb × Tai) / (Cai × Tb)} × 100
The letters in the formula have the following meanings.
Cb: Number of tested insects in untreated area Cai: Number of surviving insects in survey in untreated area Tb: Number of tested insects in treated zone Tai: Number of surviving insects in survey in treated area Here, untreated group means It means a zone that performs the same operation as the treatment zone except that the test compound is not used.
　所定濃度を１,０００ｐｐｍとし、下記の本発明化合物を供試化合物として用いて試験例２に従って試験を行った結果、下記の本発明化合物は防除価９０％以上を示した。
本発明化合物：２４，２５，３０，３１，３２，３３，３４，３５，３６，３７，４０，４３，４５，４９，５０，５６，５７，５９，６０，６１及び６２ The test of the present invention was conducted according to Test Example 2 using a compound of the present invention described below as a test compound at a predetermined concentration of 1,000 ppm. As a result, the compound of the present invention showed a control value of 90% or more.
Compounds of the present invention: 24, 25, 30, 31, 32, 33, 34, 35, 36, 37, 40, 43, 45, 49, 50, 56, 57, 59, 60, 61 and 62
試験例３
　供試化合物を製剤例５に記載の方法に準じて製剤とし、これにシンダイン（登録商標）０．０３容量％含有する水を加え、供試化合物を所定濃度含有する希釈液を調製する。
　容器に植えたイネ（Oryza sativa）苗（第２葉展開期）に該希釈液を１０ｍＬ／苗の割合で散布する。その後、トビイロウンカ３齢幼虫を２０頭放す。６日後、生存虫数を調査し、以下の式により死虫率を求める。
　　　死虫率（％）＝｛１－生存虫数／２０｝×１００ Test Example 3
A test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Syndyne (registered trademark) is added thereto to prepare a diluted solution containing a predetermined concentration of the test compound.
The diluted solution is sprayed at a rate of 10 mL / seedling to rice (Oryza sativa) seedlings (second leaf development stage) planted in a container. After that, release the 20 third instar larvae of the dead planthopper. Six days later, the number of surviving insects is examined, and the mortality rate is determined by the following equation.
Mortality rate (%) = {1-number of surviving insects / 20} x 100
　所定濃度を５００ｐｐｍとし、下記の本発明化合物を供試化合物として用いて試験例３に従って試験を行った結果、下記の本発明化合物はいずれも防除価９０％以上を示した。
本発明化合物：２２，２３，２４，２７，５５及び６２ The test was conducted according to Test Example 3 using the following compound of the present invention as a test compound with a predetermined concentration of 500 ppm. As a result, all of the following compounds of the present invention showed a control value of 90% or more.
The compound of the present invention: 22, 23, 24, 27, 55 and 62
　所定濃度を２００ｐｐｍとし、下記の本発明化合物を供試化合物として用いて試験例３に従って試験を行った結果、下記の本発明化合物はいずれも防除価９０％以上を示した。
本発明化合物：５５及び６２ The test was conducted according to Test Example 3 using a compound of the present invention described below as a test compound with a predetermined concentration of 200 ppm. As a result, each of the compounds of the present invention described below exhibited a control value of 90% or more.
The compound of the present invention: 55 and 62
試験例４
　供試化合物を製剤例５に記載の方法に準じて製剤とし、これに水を加え、供試化合物を所定濃度含有する希釈液を調製する。
　容器に該希釈液５ｍＬを加え、これに、底面に穴が開いた容器に植えたイネ苗（第２葉展開期）を収容する。７日後、トビイロウンカ３齢幼虫を２０頭放す。更に６日後、生存虫数を調査し、以下の式により死虫率を求める。
　　　死虫率（％）＝｛１－生存虫数／２０｝×１００ Test Example 4
A test compound is formulated according to the method described in Formulation Example 5, water is added thereto, and a diluted solution containing the test compound at a predetermined concentration is prepared.
In a container, 5 mL of the diluted solution is added, and to this, the rice seedling (second leaf development stage) planted in a container with a hole in the bottom is accommodated. After 7 days, release 20 third instar larvae of Tobiirounka. After six more days, the number of surviving worms is examined, and the mortality rate is determined by the following equation.
Mortality rate (%) = {1-number of surviving insects / 20} x 100
　所定濃度を１,０００ｐｐｍとし、下記の本発明化合物を供試化合物として用いて試験例４に従って試験を行った結果、下記の本発明化合物は防除価９０％以上を示した。
本発明化合物：６２ As a result of conducting a test according to Test Example 4 using a compound of the present invention described below as a test compound with a predetermined concentration of 1,000 ppm, the compound of the present invention described below exhibited a control value of 90% or more.
The compound of the present invention: 62
試験例５
　供試化合物を製剤例５に記載の方法に準じて製剤とし、これにシンダイン（登録商標）０．０３容量％含有する水を加え、供試化合物を所定濃度含有する希釈液を調製する。
　容器に植えたキャベツ（Ｂｒａｓｓｉｃａｅ　ｏｌｅｒａｃｅａ）苗（第２～３本葉展開期）に該希釈液を２０ｍＬ／苗の割合で散布する。その後、この苗の茎葉部を切り取り、ろ紙を敷いた容器内に入れる。これにハスモンヨトウ２齢幼虫５頭を放す。５日後、生存虫数を数え、次式より死虫率を求める。
　　　死虫率％＝（１－生存虫数／５）×１００ Test Example 5
A test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Syndyne (registered trademark) is added thereto to prepare a diluted solution containing a predetermined concentration of the test compound.
The diluted solution is sprayed at a rate of 20 mL / seedling to cabbage (Brassicae oleracea) seedlings (second to third leaf development stage) planted in a container. After that, the stems and leaves of this seedling are cut and placed in a container covered with filter paper. Release 5 2nd instar larvae to this. After 5 days, the number of living worms is counted, and the mortality rate is calculated from the following equation.
Mortality rate% = (1-number of surviving insects / 5) x 100
　所定濃度を５００ｐｐｍとし、下記の本発明化合物を供試化合物として用いて試験例５に従って試験を行った結果、下記の本発明化合物はいずれも死虫率８０％以上を示した。
本発明化合物：４，５，６，７，８，９，１０，１１，１２，１３，１４，１５，１６，１７，１８，１９，２０，２１，２２，２３，２４，２５，２６，２７，２９，３０，３１，３２，３３，３４，３５，３６，３７，３８，３９，４０，４１，４２，４３，４４，４５，４８，４９，５０，５１，５５，５６，５７，５９，６０，６１，６２，６３，６４及び６５ The test was conducted according to Test Example 5 using a compound of the present invention described below as a test compound at a predetermined concentration of 500 ppm. As a result, each of the compounds of the present invention described below showed a mortality of 80% or more.
Inventive compounds: 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 24, 26, 27, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 44, 45, 48, 49, 50, 51, 55, 56, 57, 59, 60, 61, 62, 63, 64 and 65
試験例６
　供試化合物を製剤例５に記載の方法に準じて製剤とし、これにシンダイン（登録商標）０．０３容量％含有する水を加え、供試化合物を所定濃度含有する希釈液を調製する。
　容器に植えたキャベツ（Brassicae oleracea）苗（第２～３本葉展開期）に該希釈液を２０ｍＬ／苗の割合で散布する。その後、この苗の茎葉部を切り取り、ろ紙を敷いた容器内に入れる。これにコナガ２齢幼虫５頭を放す。５日後、生存虫数を数え、次式より死虫率を求める。
　　　死虫率％＝（１－生存虫数／５）×１００ Test Example 6
A test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Syndyne (registered trademark) is added thereto to prepare a diluted solution containing a predetermined concentration of the test compound.
The diluted solution is sprayed at a rate of 20 mL / seedling to cabbage (Brassicae oleracea) seedlings (second to third leaf development stage) planted in a container. After that, the stems and leaves of this seedling are cut and placed in a container covered with filter paper. Release five 2nd instar larvae to this. After 5 days, the number of living worms is counted, and the mortality rate is calculated from the following equation.
Mortality rate% = (1-number of surviving insects / 5) x 100
　所定濃度を５００ｐｐｍとし、下記の本発明化合物を供試化合物として用いて試験例６に従って試験を行った結果、下記の本発明化合物はいずれも死虫率８０％以上を示した。
本発明化合物：１，４，５，６，７，８，９，１１，１２，１３，１４，１５，１６，１７，１８，１９，２０，２１，２２，２３，２４，２５，２６，２７，２９，３０，３１，３２，３３，３４，３５，３６，３７，３８，３９，４０，４１，４２，４３，４４，４５，４６，４７，４８，４９，５０，５１，５５，５６，５７，５９，６０，６１，６２，６３，６４及び６５ The test was conducted according to Test Example 6 using a compound of the present invention described below as a test compound with a predetermined concentration of 500 ppm. As a result, each of the compounds of the present invention described below showed a mortality of 80% or more.
Inventive compounds: 1, 4, 5, 6, 7, 8, 9, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 24, 26, 27, 29, 30, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 44, 45, 45, 47, 48, 49, 50, 51, 55, 56, 57, 59, 60, 61, 62, 63, 64 and 65
試験例７
　供試化合物を製剤例５に記載の方法に準じて製剤とし、これにシンダイン（登録商標）０．０３容量％含有する水を加え、供試化合物を所定濃度含有する希釈液を調製する。
　容器に植えたキャベツ苗（第３～４本葉展開期）に該希釈液を２０ｍＬ／苗の割合で散布する。その後、コナガ３齢幼虫１０頭を放す。５日後、生存虫数を数え、次式より死虫率を求める。
　　　死虫率％＝（１－生存虫数／１０）×１００ Test Example 7
A test compound is formulated according to the method described in Formulation Example 5, and water containing 0.03% by volume of Syndyne (registered trademark) is added thereto to prepare a diluted solution containing a predetermined concentration of the test compound.
The diluted solution is sprayed at a rate of 20 mL / seedling to cabbage seedlings (third to fourth leaf development stage) planted in a container. After that, let go of 10 third instar larvae of diamondback moth. After 5 days, the number of living worms is counted, and the mortality rate is calculated from the following equation.
Mortality rate% = (1-number of surviving insects / 10) x 100
　所定濃度を２００ｐｐｍとし、下記の本発明化合物を供試化合物として用いて試験例７に従って試験を行った結果、下記の本発明化合物はいずれも死虫率９０％以上を示した。
本発明化合物：４，５，６，７，８，９，１１，１２，１３，１４，１５，１６，１７，１８，２０，２１，２２，２３，２４，２５，２６，２７，２９，３０，３１，３２，３３，３４，３５，３６，３７，３８，３９，４０，４１，４２，４３，４５，４６，４８，４９，５０，５１，５５，５６，５７，５９，６０，６１及び６２ The test was conducted according to Test Example 7 using a compound of the present invention described below as a test compound with a predetermined concentration of 200 ppm. As a result, all of the compounds of the present invention described below showed a mortality of 90% or more.
The present invention compounds: 4, 5, 6, 7, 8, 9, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 29, 30, 31, 32, 23, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 45, 48, 49, 50, 51, 55, 56, 57, 59, 60, 61 and 62
試験例８
　供試化合物を１ｍｇあたり、ポリオキシエチレンソルビタンモノココエート：アセトン＝５：９５（容量比）の混合溶液５０μＬに溶解させる。これにシンダイン（登録商標）０．０３容量％含有する水を加え、供試化合物を所定濃度含有する希釈液を調製する。
　トウモロコシ（Zea mays）の若い実生を該希釈液に３０秒間浸漬する。その後、該実生２つをシャーレ（９０ｍｍ径）に入れ、これにウエスタンコーンルートワーム２齢幼虫１０頭を放す。５日後、死亡虫数を数え、次式より死虫率を求める。
　　　死虫率（％）＝（死亡虫数／１０）×１００ Test Example 8
The test compound is dissolved in 50 μL of a mixed solution of polyoxyethylene sorbitan monococoate: acetone = 5: 95 (volume ratio) per 1 mg. To this is added water containing 0.03% by volume of Syndyne (registered trademark) to prepare a diluted solution containing a predetermined concentration of the test compound.
Soak young seedlings of corn (Zea mays) for 30 seconds in the dilution. Thereafter, the two seedlings are placed in a petri dish (90 mm in diameter), and 10 western corn rootworm second instar larvae are released thereto. After 5 days, the number of dead insects is counted, and the dead insect rate is determined from the following equation.
Mortality rate (%) = (number of dead insects / 10) × 100
　所定濃度を５００ｐｐｍとし、下記の本発明化合物を供試化合物として用いて試験例８に従って試験を行った結果、下記の本発明化合物はいずれも死虫率８０％以上を示した。
本発明化合物： ５，７，８，９，１３，１４，１６，２４，２５，２６，２７，２８，２９，３０，３１，３２，３３，３４，３８，３９，４１，４５，４８，５１，５５及び５７ The test was conducted according to Test Example 8 using the following compound of the present invention as a test compound with a predetermined concentration of 500 ppm. As a result, all of the following compounds of the present invention exhibited a mortality of 80% or more.
Inventive compounds: 5,7,8,9,13,14,16,24,25,26,28,29,30,31,32,33,34,38,39,41,45,48, 51, 55 and 57
試験例９
　供試化合物を製剤例５に記載の方法に準じて製剤とし、これに水を加え、供試化合物を所定濃度含有する希釈液を調製する。
　直径５．５ｃｍのカップの内側底部に同大の濾紙を敷き、濾紙上に該希釈液０．７ｍＬを滴下し、餌として該カップにショ糖３０ｍｇを均一に入れる。該カップにイエバエ雌成虫１０頭を放ち、蓋をする。２４時間後にイエバエの死亡虫数を数え、死虫率を求める。死虫率は下式により計算する。
　　　死虫率（％）＝（死亡虫数／供試虫数）×１００ Test Example 9
A test compound is formulated according to the method described in Formulation Example 5, water is added thereto, and a diluted solution containing the test compound at a predetermined concentration is prepared.
The same size filter paper is placed on the inner bottom of a 5.5 cm diameter cup, and 0.7 mL of the diluted solution is dropped on the filter paper, and 30 mg of sucrose is uniformly poured into the cup as a bait. Release 10 adult housefly female adults into the cup and cover. After 24 hours, count the number of dead insects in the housefly and determine the mortality rate. The mortality rate is calculated by the following formula.
Mortality rate (%) = (number of dead insects / number of test insects) x 100
　所定濃度を５００ｐｐｍとし、下記の本発明化合物を供試化合物として用いて試験例９に従って試験を行った結果、下記の本発明化合物はいずれも死虫率１００％を示した。
本発明化合物：２１，２３，２４，２５，２６，３０，３１，３３，３４，４９，５５及び５７ The test was conducted according to Test Example 9 using a compound of the present invention described below as a test compound with a predetermined concentration of 500 ppm. As a result, each of the compounds of the present invention described below showed a mortality of 100%.
The compounds of the present invention: 21, 23, 24, 25, 26, 30, 31, 33, 34, 49, 55 and 57
試験例１０
　供試化合物を製剤例５に記載の方法に準じて製剤とし、これに水を加え、供試化合物を所定濃度含有する希釈液を調製する。
　直径５．５ｃｍのカップの内側底部に同大の濾紙を敷き、濾紙上に該希釈液０．７ｍＬを滴下し、餌として該カップにショ糖３０ｍｇを均一に入れる。該カップにチャバネゴキブリ雄成虫２頭を放ち、蓋をする。６日後にチャバネゴキブリの死亡虫数を数え、次式により死虫率を求める。
　　　死虫率（％）＝（死亡虫数／供試虫数）×１００ Test Example 10
A test compound is formulated according to the method described in Formulation Example 5, water is added thereto, and a diluted solution containing the test compound at a predetermined concentration is prepared.
The same size filter paper is placed on the inner bottom of a 5.5 cm diameter cup, and 0.7 mL of the diluted solution is dropped on the filter paper, and 30 mg of sucrose is uniformly poured into the cup as a bait. Put two male adult German cockroaches into the cup and cover. Six days later, the number of dead insects of the German cockroach is counted, and the mortality rate is determined by the following equation.
Mortality rate (%) = (number of dead insects / number of test insects) x 100
　所定濃度を５００ｐｐｍとし、下記の本発明化合物を供試化合物として用いて試験例１０に従って試験を行った結果、下記の本発明化合物はいずれも死虫率１００％を示した。
本発明化合物：３０及び４９ The test was conducted according to Test Example 10 using a compound of the present invention described below as a test compound with a predetermined concentration of 500 ppm. As a result, each of the compounds of the present invention described below showed a mortality of 100%.
The compound of the present invention: 30 and 49
試験例１１
　本発明化合物１ｍｇを、キシレン：ＤＭＦ：界面活性剤＝４：４：１（容量比）の混合溶液１０μＬに溶解し、展着剤０．０２容量％含有する水で希釈して、本発明化合物を所定濃度含有する希釈液Ａを調製する。
　本成分１ｍｇを、キシレン：ＤＭＦ：界面活性剤＝４：４：１（容量比）の混合溶液１０μＬに溶解し、展着剤０．０２容量％含有する水で希釈して、本成分を所定濃度含有する希釈液Ｂを調製する。
　希釈液Ａと希釈液Ｂとを混合し、希釈液Ｃを得る。
　キュウリ子葉の葉片（長さ１．５ｃｍ）を２４穴マイクロプレートの各ウェルに収容し、１ウェルあたりワタアブラムシ無翅成虫２匹及び幼虫８匹を放し、１ウェルあたり２０μＬの希釈液Ｃを散布する。これを処理区とする。
　なお、希釈液Ｃの代わりに展着剤０．０２容量％を含有する水を２０μＬ散布するウェルを無処理区とする。
　希釈液Ｃが乾燥した後、マイクロプレート上部をフィルムシートで覆う。５日後に、各ウェルの生存虫数を調査する。
　防除価を次式より算出する。
　　　防除価（％）＝｛１－（Ｔａｉ）／（Ｃａｉ）｝×１００
なお、式中の記号は以下の意味を表す。
　　　Ｃａｉ：無処理区の調査時の生存虫数
　　　Ｔａｉ：処理区の調査時の生存虫数 Test Example 11
The compound of the present invention is prepared by dissolving 1 mg of the compound of the present invention in 10 μL of a mixed solution of xylene: DMF: surfactant = 4: 4: 1 (volume ratio), and diluting with water containing 0.02 vol% of the spreading agent. The dilution liquid A containing a predetermined concentration is prepared.
1 mg of this component is dissolved in 10 μL of a mixed solution of xylene: DMF: surfactant = 4: 4: 1 (volume ratio), diluted with water containing 0.02 volume% of spreading agent, and the component is specified. Prepare diluent B containing the concentration.
Dilution A and dilution B are mixed to obtain dilution C.
Store cucumber cotyledon leaf pieces (1.5 cm in length) in each well of a 24-well microplate, release 2 cotton aphid infested adults and 8 larvae per well, and apply 20 μL of diluent C per well Do. Let this be a treatment area.
In addition, a well to which 20 μL of water containing 0.02% by volume of a spreading agent is sprayed instead of the dilution liquid C is regarded as a non-treatment zone.
After the diluent C is dried, the top of the microplate is covered with a film sheet. After 5 days, the number of viable worms in each well is examined.
The control value is calculated by the following equation.
Control value (%) = {1- (Tai) / (Cai)} × 100
The symbols in the formulas have the following meanings.
Cai: Number of surviving insects at survey in untreated area Tai: Number of viable insects at survey in treated area
　試験例１１にて、効果を確認することができる具体的な希釈液Ｃについて、下記１）～５）に示す。 Specific dilutions C whose effects can be confirmed in Test Example 11 are shown in the following 1) to 5).
１）リストＡに記載の組み合わせにおいて、本発明化合物の濃度が２００ｐｐｍであり、本成分の濃度が２,０００ｐｐｍである希釈液Ｃ。なお、リストＡにおいて、Comp Xは、本発明化合物１～６５から選ばれるいずれか１つの化合物を意味する。
リストＡ：
Comp X + クロチアニジン；Comp X + チアメトキサム；Comp X + イミダクロプリド；Comp X + チアクロプリド；Comp X + フルピラジフロン；Comp X + スルホキサフロル；Comp X + トリフルメゾピリム；Comp X + ジクロロメゾチアズ；Comp X + ベータシフルトリン；Comp X + テフルトリン；Comp X + フィプロニル；Comp X + クロラントラニリプロール；Comp X + シアントラニリプロール；Comp X + テトラニリプロール；Comp X + チオジカルブ；Comp X + カルボフラン；Comp X + フルキサメタミド；Comp X + アフォキソラネル；Comp X + フルララネル；Comp X + ブロフラニリド；Comp X + アバメクチン；Comp X + フルオピラム；Comp X + フルエンスルホン；Comp X + フルアザインドリジン；Comp X + チオキサザフェン；Comp X + フルピリミン；Comp X + 菌根菌；Comp X + ブラディリゾビウム・ジャポニカムＴＡ－１１株；Comp X + バチルス・フィルムス；Comp X + バチルス・フィルムスＩ－１５８２株；Comp X + バチルス・アミロリケファシエンス；Comp X + バチルス・アミロリケファシエンスＦＺＢ４２株；Comp X + パスツーリア・ニシザワエ；Comp X + パスツーリア・ニシザワエＰｎ１株；Comp X + パスツーリア・ペネトランス；Comp X + テブコナゾール；Comp X + プロチオコナゾール；Comp X + メトコナゾール；Comp X + イプコナゾール；Comp X + トリチコナゾール；Comp X + ジフェノコナゾール；Comp X + イマザリル；Comp X + トリアジメノール；Comp X + テトラコナゾール；Comp X + フルトリアホール；Comp X + マンデストロビン；Comp X + アゾキシストロビン；Comp X + ピラクロストロビン；Comp X + トリフロキシストロビン；Comp X + フルオキサストロビン；Comp X + ピコキシストロビン；Comp X + フェナミドン；Comp X + メタラキシル；Comp X + メタラキシルＭ；Comp X + フルジオキソニル；Comp X + セダキサン；Comp X + ペンフルフェン；Comp X + フルキサピロキサド；Comp X + ベンゾビンジフルピル；Comp X + ボスカリド；Comp X + カルボキシン；Comp X + ペンチオピラド；Comp X + フルトラニル；Comp X + キャプタン；Comp X + チウラム；Comp X + トルクロホスメチル；Comp X + チアベンダゾール；Comp X + エタボキサム；Comp X + マンコゼブ；Comp X + ピカルブトラゾクス；Comp X + オキサチアピプロリン；Comp X + シルチオファム； Comp X + インピルフルキサム。 1) Dilution C wherein the concentration of the compound of the present invention is 200 ppm and the concentration of this component is 2,000 ppm among the combinations described in List A. In List A, Comp X means any one compound selected from the compounds of the present invention 1 to 65.
List A:
Comp X + Clothianidin; Comp X + Thiamethoxam; Comp X + Imidacloprid; Comp X + Thiacloprid; Comp X + Flupyradi flon; Comp X + Sulfoxafolate; Comp X + Triflumesospirim; Comp X + tefluthrin; Comp X + fipronil; Comp X + chlorantraniliprole; Comp X + cyantrani liprole; Comp X + tetraniliprole; Comp X + thiodicarb; Comp X + carbofuran; Comp X + fluxamethamide Comp X + Afoxoranel; Comp X + Flulara Nerel; Comp X + Burofuranilide; Comp X + Abamectin; Comp X + Fluopyram; Comp X + Fluene Sulfone; Comp X + Fluazaindolizine; Comp X + Thioxazaphene; Comp X + Mycorrhizal fungus; Comp X + Brady Rhizobium ・ Japonicum TA 11 strains; Comp X + Bacillus filmes; Comp X + Bacillus films I 1582 strain; Comp X + Bacillus amyloliquefaciens; Comp X + Bacillus amyloliquefaciens FZB 42 strain; Comp X + Pasteuria Comps X + Pasteuria spp. Pn 1 strain; Comp X + Pasteuria sp. Penetrans; Comp X + Tebuconazole; Comp X + Prothioconazole; Comp X + Metconazole; Comp X + Ipconazole; Comp X + Triticonazole; Comp X + Imazalil; Comp X + Triazimenol; Comp X + Tetraconazole; Comp X + Flutriaphor; Comp X + Mandestrobin; Comp X + Azoxystrobin; Comp X + Pyraclostrobin; Comp X + Trifloxystrobin; Comp X + Full Oxastrobin; Comp X + Picoxy Strobi Comp X + phenamidone; Comp X + metalaxyl; Comp X + metalaxyl M; Comp X + fludioxonil; Comp X + sedaxane; Comp X + penflufen; Comp X + fluxapiroxide; Comp X + benzobin diflupyr; Comp X + Carboxin; Comp X + Flutolanil; Comp X + Captan; Comp X + Thiuram; Comp X + Tolclophos Methyl; Comp X + Thiabendazole; Comp X + Etaboxam; Comp X + Mancozeb; Comp X + Picalbutrazox; Comp X + oxathiapiproline; Comp X + silthiofam; Comp X + impilfluxam.
２）リストＡに記載の組み合わせにおいて、本発明化合物の濃度が２００ｐｐｍであり、本成分の濃度が２００ｐｐｍである希釈液Ｃ。 2) Dilution C wherein the concentration of the compound of the present invention is 200 ppm and the concentration of this component is 200 ppm in the combinations described in List A.
３）リストＡに記載の組み合わせにおいて、本発明化合物の濃度が５００ｐｐｍであり、本成分の濃度が５０ｐｐｍである希釈液Ｃ。 3) Dilution C wherein the concentration of the compound of the present invention is 500 ppm and the concentration of this component is 50 ppm in the combinations described in List A.
４）リストＡに記載の組み合わせにおいて、本発明化合物の濃度が５００ｐｐｍであり、本成分の濃度が５ｐｐｍである希釈液Ｃ。 4) Dilution C wherein the concentration of the compound of the present invention is 500 ppm and the concentration of this component is 5 ppm in the combinations described in List A.
５）リストＡに記載の組み合わせにおいて、本発明化合物の濃度が５００ｐｐｍであり、本成分の濃度が０．５ｐｐｍである希釈液Ｃ。 5) Dilution C wherein the concentration of the compound of the present invention is 500 ppm and the concentration of this component is 0.5 ppm in the combinations described in List A.
比較試験例
　供試化合物を製剤例５に記載の方法に準じて製剤とし、これに水を加え、これにシンダイン（登録商標）０．０３容量％含有する水を加え、供試化合物を所定濃度含有する希釈液を調製する。
　容器に植えたキャベツ（Ｂｒａｓｓｉｃａｅ　ｏｌｅｒａｃｅａ）苗（第５～６本葉展開期）に該希釈液を２０ｍＬ／苗の割合で散布する。その後、ハスモンヨトウ４齢幼虫１０頭を放す。６日後、生存虫数を数え、次式より死虫率を求める。
　　　死虫率（％）＝（１－生存虫数／１０）×１００
　各濃度における死虫率を［表１０］に記す。
Figure JPOXMLDOC01-appb-C000073
 Comparative Test Example A test compound is prepared according to the method described in Preparation Example 5, water is added thereto, water containing 0.03% by volume of Syndyne (registered trademark) is added thereto, and the test compound is added to a predetermined concentration. Prepare the dilution to contain.
The diluted solution is sprayed at a rate of 20 mL / seedling to cabbage (Brassicae oleracea) seedlings (fifth to sixth leaf development stage) planted in a container. Then release 10 4th instar larvae. Six days later, the number of living insects is counted, and the mortality rate is calculated from the following equation.
Mortality rate (%) = (1-number of surviving insects / 10) x 100
The mortality rate at each concentration is described in [Table 10].
Figure JPOXMLDOC01-appb-C000073
Figure JPOXMLDOC01-appb-T000074
Figure JPOXMLDOC01-appb-T000074
　本発明化合物は、有害節足動物に対して優れた防除効果を示す。 The compounds of the present invention exhibit excellent control effects against harmful arthropods.

Claims (12)

  1. 　式（Ｉ）：
    Figure JPOXMLDOC01-appb-C000001
     ［式中、
    　Ａ１は、ＮＣＨ３、酸素原子又は硫黄原子を表し、
    　Ａ２は、窒素原子又はＣＨを表し、
    　Ｒ１は、Ｃ１－Ｃ３ペルフルオロアルキル基、Ｃ１－Ｃ３ペルフルオロアルコキシ基、Ｃ１－Ｃ３ペルフルオロアルキルスルファニル基、Ｃ１－Ｃ３ペルフルオロアルキルスルフィニル基、又はＣ１－Ｃ３ペルフルオロアルキルスルホニル基を表し、
    　Ｒ２は、１以上のハロゲン原子を有していてもよいＣ２－Ｃ５鎖式炭化水素基、１以上のハロゲン原子を有していてもよい（Ｃ１－Ｃ２アルコキシ）Ｃ１－Ｃ２アルキル基、群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル基、又は（群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル）Ｃ１－Ｃ２アルキル基を表し、
    　ｎは、０、１又は２を表す。
    　群Ｘ：シアノ基及びハロゲン原子からなる群。］
    で示される化合物、又はそのＮ－オキシド。     Formula (I):
    Figure JPOXMLDOC01-appb-C000001
     [In the formula,
    A 1 represents NCH 3 , an oxygen atom or a sulfur atom,
    A 2 represents a nitrogen atom or CH,
    R 1 represents a C1 to C3 perfluoroalkyl group, a C1 to C3 perfluoroalkoxy group, a C1 to C3 perfluoroalkylsulfanyl group, a C1 to C3 perfluoroalkylsulfinyl group, or a C1 to C3 perfluoroalkylsulfonyl group,
    R 2 is a C2-C5 chain hydrocarbon group which may have one or more halogen atoms, (C1-C2 alkoxy) C1-C2 alkyl group which may have one or more halogen atoms, a group A cyclopropyl group which may have one or more substituents selected from X, or (a cyclopropyl group optionally having one or more substituents selected from group X) C1-C2 alkyl group,
    n represents 0, 1 or 2;
    Group X: a group consisting of a cyano group and a halogen atom. ]
    Or a N-oxide thereof.
  2. 　Ｒ２が、１以上のハロゲン原子を有していてもよいＣ２－Ｃ３鎖式炭化水素基、群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル基、又は（群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル）メチル基である、請求項１記載の化合物。 R 2 is a C2-C3 chain hydrocarbon group optionally having one or more halogen atoms, a cyclopropyl group optionally having one or more substituents selected from Group X, or (group X The compound according to claim 1, which is a cyclopropyl) methyl group which may have one or more substituents selected from the group consisting of
  3. 　Ｒ１が、トリフルオロメチル基、トリフルオロメトキシ基、トリフルオロメチルスルファニル基、トリフルオロメチルスルフィニル基、又はトリフルオロメチルスルホニル基である、請求項１又は請求項２記載の化合物。 The compound according to claim 1 or 2, wherein R 1 is a trifluoromethyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group.
  4. 　Ａ１及びＡ２の組み合わせが、Ａ１がＮＣＨ３であり、Ａ２が窒素原子である組み合わせか、又はＡ１が酸素原子であり、Ａ２がＣＨである組み合わせである、請求項１～請求項３のいずれか一項に記載の化合物。 The combination of A 1 and A 2 is a combination in which A 1 is NCH 3 and A 2 is a nitrogen atom, or a combination in which A 1 is an oxygen atom and A 2 is CH. A compound according to any one of the claims 3.
  5. 　Ａ１がＮＣＨ３であり、Ａ２が窒素原子である、請求項１～請求項３のいずれか一項に記載の化合物。 The compound according to any one of claims 1 to 3 , wherein A 1 is NCH 3 and A 2 is a nitrogen atom.
  6. 　Ａ１が酸素原子であり、Ａ２がＣＨである、請求項１～請求項３のいずれか一項に記載の化合物。 The compound according to any one of claims 1 to 3, wherein A 1 is an oxygen atom and A 2 is CH.
  7. 　請求項１～請求項６のいずれか一項に記載の化合物と、不活性担体とを含有する有害節足動物防除組成物。 A harmful arthropod control composition comprising the compound according to any one of claims 1 to 6 and an inert carrier.
  8. 　請求項１～請求項６のいずれか一項に記載の化合物の有効量を有害節足動物又は有害節足動物の生息場所に施用する有害節足動物の防除方法。 A method for controlling noxious arthropods which comprises applying an effective amount of the compound according to any one of claims 1 to 6 to a harmful arthropod or a habitat of the harmful arthropod.
  9. 　群（ａ）及び群（ｂ）からなる群より選ばれる１以上の成分、並びに請求項１～請求項６のいずれか一項に記載の化合物を含有する組成物：
    　群（ａ）：殺虫活性成分、殺ダニ活性成分及び殺線虫活性成分からなる群；
    　群（ｂ）：殺菌活性成分。     A composition containing one or more components selected from the group consisting of group (a) and group (b), and the compound according to any one of claims 1 to 6.
    Group (a): a group consisting of an insecticidal active ingredient, an acaricidal active ingredient and a nematode active ingredient;
    Group (b): bactericidal active ingredient.
  10. 　式（Ｘ）：
    Figure JPOXMLDOC01-appb-C000002
     ［式中、
    　Ｒｘは、ＯＲ２、フッ素原子又は塩素原子を表し、
    　Ｒ２は、１以上のハロゲン原子を有していてもよいＣ２－Ｃ５鎖式炭化水素基、１以上のハロゲン原子を有していてもよい（Ｃ１－Ｃ２アルコキシ）Ｃ１－Ｃ２アルキル基、群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル基、又は（群Ｘより選ばれる１以上の置換基を有していてもよいシクロプロピル）Ｃ１－Ｃ２アルキル基を表し、
    　ｎは、０、１又は２を表し、
    　Ｒｙは、シアノ基、カルボキシ基、メトキシカルボニル基又はエトキシカルボニル基を表す。
    　群Ｘ：シアノ基及びハロゲン原子からなる群。］で示される化合物。     Formula (X):
    Figure JPOXMLDOC01-appb-C000002
     [In the formula,
    R x represents OR 2 , a fluorine atom or a chlorine atom,
    R 2 is a C2-C5 chain hydrocarbon group which may have one or more halogen atoms, (C1-C2 alkoxy) C1-C2 alkyl group which may have one or more halogen atoms, a group A cyclopropyl group which may have one or more substituents selected from X, or (a cyclopropyl group optionally having one or more substituents selected from group X) C1-C2 alkyl group,
    n represents 0, 1 or 2;
    R y represents a cyano group, a carboxy group, a methoxycarbonyl group or an ethoxycarbonyl group.
    Group X: a group consisting of a cyano group and a halogen atom. The compound shown by].
  11. 　請求項７もしくは請求項９に記載の組成物の有効量を有害節足動物又は有害節足動物の生息場所に施用する有害節足動物の防除方法。 A method for controlling noxious arthropods, which comprises applying an effective amount of the composition according to claim 7 or 10 to a harmful arthropod or a habitat of the harmful arthropod.
  12. 　請求項１～請求項６のいずれか一項に記載の化合物の有効量又は請求項７もしくは請求項９に記載の組成物の有効量を保持している種子又は栄養生殖器官。 A seed or vegetative organ which holds an effective amount of the compound according to any one of claims 1 to 6 or an effective amount of the composition according to claim 7 or 9.
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20200071320A1 (en) * 2017-03-23 2020-03-05 Sumitomo Chemical Company, Limited Fused heterocyclic compound and composition containing same
WO2020084075A1 (en) 2018-10-24 2020-04-30 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfoximine containing substituents
WO2021105399A1 (en) 2019-11-27 2021-06-03 Syngenta Crop Protection Ag Process for the preparation of 5-chloro-pyridine-2-carboxylic acids and carboxylates with 3-sulfur containing substituents
WO2021175959A1 (en) 2020-03-04 2021-09-10 Syngenta Crop Protection Ag Process for the preparation of 5-chloro-3-alkylsulfanyl-pyridine-2-carboxylic acid amides and carboxylates
WO2021219810A1 (en) 2020-04-30 2021-11-04 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014005263A (en) * 2011-08-04 2014-01-16 Sumitomo Chemical Co Ltd Condensed heterocyclic compound and use thereof for pest control
WO2016039441A1 (en) * 2014-09-12 2016-03-17 日本農薬株式会社 Imidazopyridazine compound or salts thereof and agricultural and horticultural insecticide containing said compound and method of using same
WO2016059145A1 (en) * 2014-10-16 2016-04-21 Syngenta Participations Ag Pesticidally active tetracyclic heterocyclic derivatives with sulphur containing substituents
WO2016125622A1 (en) * 2015-02-03 2016-08-11 住友化学株式会社 Benzoxazole compound, and use thereof for noxious arthropod control
WO2016125621A1 (en) * 2015-02-03 2016-08-11 住友化学株式会社 Benzimidazole compound, and use thereof for noxious arthropod control
WO2017094750A1 (en) * 2015-12-01 2017-06-08 日本農薬株式会社 3h-pyrrolopyridine compound or n-oxide thereof, or salts thereof, agricultural and horticultural insecticide containing compound, and use thereof
JP2017526678A (en) * 2014-08-25 2017-09-14 シンジェンタ パーティシペーションズ アーゲー Pesticide active heterocyclic derivatives with sulfur-containing substituents
JP2018076354A (en) * 2017-12-26 2018-05-17 住友化学株式会社 Pest control composition and pest control method
WO2018139436A1 (en) * 2017-01-24 2018-08-02 住友化学株式会社 Fused heterocyclic compound and composition containing same

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014005263A (en) * 2011-08-04 2014-01-16 Sumitomo Chemical Co Ltd Condensed heterocyclic compound and use thereof for pest control
JP2017526678A (en) * 2014-08-25 2017-09-14 シンジェンタ パーティシペーションズ アーゲー Pesticide active heterocyclic derivatives with sulfur-containing substituents
WO2016039441A1 (en) * 2014-09-12 2016-03-17 日本農薬株式会社 Imidazopyridazine compound or salts thereof and agricultural and horticultural insecticide containing said compound and method of using same
WO2016059145A1 (en) * 2014-10-16 2016-04-21 Syngenta Participations Ag Pesticidally active tetracyclic heterocyclic derivatives with sulphur containing substituents
WO2016125622A1 (en) * 2015-02-03 2016-08-11 住友化学株式会社 Benzoxazole compound, and use thereof for noxious arthropod control
WO2016125621A1 (en) * 2015-02-03 2016-08-11 住友化学株式会社 Benzimidazole compound, and use thereof for noxious arthropod control
WO2017094750A1 (en) * 2015-12-01 2017-06-08 日本農薬株式会社 3h-pyrrolopyridine compound or n-oxide thereof, or salts thereof, agricultural and horticultural insecticide containing compound, and use thereof
WO2018139436A1 (en) * 2017-01-24 2018-08-02 住友化学株式会社 Fused heterocyclic compound and composition containing same
JP2018076354A (en) * 2017-12-26 2018-05-17 住友化学株式会社 Pest control composition and pest control method

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20200071320A1 (en) * 2017-03-23 2020-03-05 Sumitomo Chemical Company, Limited Fused heterocyclic compound and composition containing same
US10934287B2 (en) * 2017-03-23 2021-03-02 Sumitomo Chemical Company, Limited Fused heterocyclic compound and composition containing same
WO2020084075A1 (en) 2018-10-24 2020-04-30 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfoximine containing substituents
WO2021105399A1 (en) 2019-11-27 2021-06-03 Syngenta Crop Protection Ag Process for the preparation of 5-chloro-pyridine-2-carboxylic acids and carboxylates with 3-sulfur containing substituents
WO2021175959A1 (en) 2020-03-04 2021-09-10 Syngenta Crop Protection Ag Process for the preparation of 5-chloro-3-alkylsulfanyl-pyridine-2-carboxylic acid amides and carboxylates
CN115210220A (en) * 2020-03-04 2022-10-18 先正达农作物保护股份公司 Process for the preparation of 5-chloro-3-alkylsulfanyl-pyridine-2-carboxylic acid amides and formates
WO2021219810A1 (en) 2020-04-30 2021-11-04 Syngenta Crop Protection Ag Pesticidally active heterocyclic derivatives with sulfur containing substituents

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