WO2019065568A1 - Composé hétérocyclique et agent de lutte contre les arthropodes nuisibles contenant celui-ci - Google Patents

Composé hétérocyclique et agent de lutte contre les arthropodes nuisibles contenant celui-ci Download PDF

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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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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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    • 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.

Abstract

La présente invention concerne : un composé représenté par la formule (I) qui a un excellent effet de lutte contre les arthropodes nuisibles [dans la formule, A1 représente NCH3 ou similaire, A2 représente un atome d'azote ou similaire, R1 représente un groupe perfluoroalkyle en C1-C3 ou similaire, R2 représente un groupe hydrocarboné à chaîne en C2-C5 ayant éventuellement un ou plusieurs atomes d'halogène ou similaire, n représente 0 ou similaire, le groupe X : groupe constitué d'un groupe cyano et d'un atome d'halogène].L'invention concerne également un intermédiaire de production du composé ; une composition contenant celui-ci ; et une composition contenant le composé, un ou plusieurs composants choisis dans le groupe constitué par le groupe (a) et le groupe (b), ainsi qu'un porteur inerte.
PCT/JP2018/035296 2017-09-26 2018-09-25 Composé hétérocyclique et agent de lutte contre les arthropodes nuisibles contenant celui-ci WO2019065568A1 (fr)

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US20200071320A1 (en) * 2017-03-23 2020-03-05 Sumitomo Chemical Company, Limited Fused heterocyclic compound and composition containing same
WO2020084075A1 (fr) 2018-10-24 2020-04-30 Syngenta Crop Protection Ag Dérivés hétérocycliques à action pesticide avec des substituants contenant de la sulfoximine
WO2021105399A1 (fr) 2019-11-27 2021-06-03 Syngenta Crop Protection Ag Procédé de préparation d'acides 5-chloro-pyridine-2-carboxyliques et de carboxylates avec des substituants contenant 3 atomes de soufre
WO2021175959A1 (fr) 2020-03-04 2021-09-10 Syngenta Crop Protection Ag Procédé de préparation de carboxylates et d'amides d'acide 5-chloro-3-alkylsulfanyl-pyridine-2-carboxylique
WO2021219810A1 (fr) 2020-04-30 2021-11-04 Syngenta Crop Protection Ag Dérivés hétérocycliques à action pesticide comprenant des substituants contenant du soufre

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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 (fr) 2018-10-24 2020-04-30 Syngenta Crop Protection Ag Dérivés hétérocycliques à action pesticide avec des substituants contenant de la sulfoximine
WO2021105399A1 (fr) 2019-11-27 2021-06-03 Syngenta Crop Protection Ag Procédé de préparation d'acides 5-chloro-pyridine-2-carboxyliques et de carboxylates avec des substituants contenant 3 atomes de soufre
WO2021175959A1 (fr) 2020-03-04 2021-09-10 Syngenta Crop Protection Ag Procédé de préparation de carboxylates et d'amides d'acide 5-chloro-3-alkylsulfanyl-pyridine-2-carboxylique
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WO2021219810A1 (fr) 2020-04-30 2021-11-04 Syngenta Crop Protection Ag Dérivés hétérocycliques à action pesticide comprenant des substituants contenant du soufre

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