WO2020022360A1 - Pyridone compound and agricultural and horticultural fungicide having this as active component - Google Patents

Pyridone compound and agricultural and horticultural fungicide having this as active component Download PDF

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Publication number
WO2020022360A1
WO2020022360A1 PCT/JP2019/028942 JP2019028942W WO2020022360A1 WO 2020022360 A1 WO2020022360 A1 WO 2020022360A1 JP 2019028942 W JP2019028942 W JP 2019028942W WO 2020022360 A1 WO2020022360 A1 WO 2020022360A1
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group
substituent
optionally substituted
group optionally
formula
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PCT/JP2019/028942
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French (fr)
Japanese (ja)
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豪毅 梅谷
英明 生島
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三井化学アグロ株式会社
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Priority to JP2020532428A priority Critical patent/JP7328222B2/en
Publication of WO2020022360A1 publication Critical patent/WO2020022360A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to a pyridone compound and an agricultural chemical containing the compound as an active ingredient.
  • 1,3,5,6-substituted-2-pyridone compounds for example, 1,3,5,6-substituted-2 compounds having an aryl group or a heteroaryl group at the 3-position as GABA alpha-2 / 3 ligand -Pyridone compounds have been disclosed (see, for example, WO 98/55480). Further, as a therapeutic agent for bacterial infection, a 1,3,5,6-substituted-2-pyridone compound having a carboxyl group at the 3-position has been disclosed (see, for example, European Patent No. 0308020).
  • An object of the present invention is to provide a novel compound which is effective as an agricultural and horticultural fungicide.
  • the present inventors have conducted intensive studies on the 1,3,5,6-substituted-2-pyridone compound group and the 1,5,6-substituted-2-pyridone compound group in order to solve the above problems.
  • a novel group of compounds in which an optionally substituted thiophen-2-yl group or an optionally substituted thiophen-3-yl group has been introduced, against a plant disease They have found that they exert excellent control activity, and have completed the present invention.
  • R1 is Hydroxyl group, Cyano group, A C1-C6 alkyl group optionally substituted with a substituent A, A C1-C6 haloalkyl group, A C3-C8 cycloalkyl group optionally substituted with a substituent A, A C2-C6 alkenyl group optionally substituted with a substituent A, A C2-C6 haloalkenyl group, A C2-C6 alkynyl group optionally substituted with a substituent A, A C2-C6 haloalkynyl group, A C1-C6 alkoxy group optionally substituted with a substituent A, C1-C6 haloalkoxy groups, A C3-C8 cycloalkoxy group optionally substituted with a substituent A, A C2-C6 alkenyloxy group optionally substituted with a substituent A, A C2-C6 haloalkenyloxy
  • R2, R3 and R4 are each independently; Hydrogen atom, Halogen atom, Hydroxyl group, Cyano group, Nitro group, A C1-C6 alkyl group optionally substituted with a substituent C, A C1-C6 haloalkyl group, A C3-C8 cycloalkyl group optionally substituted with a substituent C, A C2-C6 alkenyl group optionally substituted with a substituent C, A C2-C6 haloalkenyl group, A C2-C6 alkynyl group optionally substituted with a substituent C, A C2-C6 haloalkynyl group, A C1-C6 alkoxy group optionally substituted with a substituent C, C1-C6 haloalkoxy groups, A C3-C8 cycloalkoxy group optionally substituted with a substituent C, A C2-C6 alkenyloxy group optionally substituted with a substituent C, A C2-C6 haloal
  • R1 is Cyano group, A C1-C6 alkyl group optionally substituted with a substituent A, A C1-C6 haloalkyl group, A C3-C8 cycloalkyl group optionally substituted with a substituent A, A C2-C6 alkenyl group optionally substituted with a substituent A, A C2-C6 haloalkenyl group, A C2-C6 alkynyl group optionally substituted with a substituent A, Or a C2-C6 haloalkynyl group;
  • R2, R3 and R4 are each independently; Hydrogen atom, Halogen atom, Hydroxyl group, Cyano group, A C1-C6 alkyl group optionally substituted with a substituent C, A C1-C6 haloalkyl group, A C2-C6 alkenyl group optionally substituted with a substituent C, A C2-C6 alkynyl group optionally substituted with a substituent C, A C
  • R1 is A C1-C6 alkyl group optionally substituted with a substituent A, Or a C1-C6 haloalkyl group
  • R2, R3 and R4 are each independently; Hydrogen atom, Halogen atom, Hydroxyl group, Cyano group, A C1-C6 alkyl group optionally substituted with a substituent C, Or a C1-C6 alkoxy group optionally substituted with a substituent C
  • R5 is Hydrogen atom, Halogen atom, A C1-C6 alkyl group optionally substituted with a substituent A, A C1-C6 haloalkyl group, Or a C2-C6 alkynyl group optionally substituted with a substituent A
  • R6 is Halogen atom, Cyano group, A C1-C6 alkyl group optionally substituted with a substituent C, A C1-C6 haloalkyl group, Or the compound according to [2], which represents a C1 to C
  • R2, R3 and R4 are each independently Hydrogen atom, Halogen atom, Hydroxyl group, Cyano group, Nitro group, A C1-C6 alkyl group optionally substituted with a substituent C, A C1-C6 haloalkyl group, A C3-C8 cycloalkyl group optionally substituted with a substituent C, A C2-C6 alkenyl group optionally substituted with a substituent C, A C2-C6 haloalkenyl group, A C2-C6 alkynyl group optionally substituted with a substituent C, A C2-C6 haloalkynyl group, A C1-C6 alkoxy group optionally substituted with a substituent C, C1-C6 haloalkoxy groups, A C3-C8 cycloalkoxy group optionally substituted with a substituent C, A C2-C6 alkenyloxy group optionally substituted with a substituent C, A C2-C6 alkenyloxy
  • a method for controlling plant diseases comprising applying the pesticidal composition for agricultural and horticultural use according to [5] to plants, plant seeds, or soil for cultivating plants.
  • a method for controlling plant diseases comprising applying the fungicide for agricultural and horticultural use according to [6] to plants, plant seeds, or soil for cultivating plants.
  • a novel compound that is effective as an agricultural and horticultural fungicide can be provided.
  • Cx to Cy indicates that the compound has x to y carbon atoms.
  • x and y represent integers, and it is understood that all integers present between x and y are also individually disclosed.
  • C1-C6 has 1, 2, 3, 4, 5, or 6 carbon atoms
  • C1-C5 has 1, 2, 3, 4, or 5 carbon atoms
  • C1-C3 has 1, 2, or 3 carbon atoms
  • C2-C6 has 2, 3, 4, 5, or 6 carbon atoms
  • C3-C8 has 3, 4, 5, 6, 7, or Eight carbon atoms
  • C3-C6 means having three, four, five, or six carbon atoms, respectively.
  • optionally substituted means substituted or unsubstituted.
  • the number of substituents when the number of substituents is not specified, it indicates that the number of substituents is 1.
  • the number of substituents is specified as “may be substituted with 0 to 5 as appropriate”, it is understood that all integers present between 0 and 5 are also individually disclosed. Is done. That is, it means that the substituent has none, 1, 2, 3, 4, or 5 substituents.
  • the number of substituents may be none, 1, 2, 3, or 4, and in “optionally substituted with 0 to 3”, none.
  • the expression “may be substituted with 0 to 2 substituents” for 1, 2, or 3 substituents means none, 1 or 2 substituents, respectively.
  • the C1-C6 alkyl group may be linear or branched, and specifically, includes a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group.
  • Pentyl isopentyl, 1-methylbutyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3 -Methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl , 2,3-dimethylbutyl, 2-ethylbutyl, 1-isopropylpropyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl And a ropyl group.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • C1 to C6 haloalkyl group means a C1 to C6 alkyl group in which a hydrogen atom is arbitrarily substituted by one or more halogen atoms.
  • those halogen atoms may be the same or different, and the number of substitution is not particularly limited as long as it can be present as a substituent.
  • C1 to C6 haloalkyl groups include monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, monobromomethyl, monoiodomethyl, chlorodifluoromethyl, bromodifluoromethyl, -Fluoroethyl group, 2-fluoroethyl group, 1,1-difluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group Pentafluoroethyl group, 2,2,2-trichloroethyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 2,2,2 -Trifluoro-1- (trifluoromethyl) ethyl group, nonafluorobut
  • C3-C8 cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.
  • the C2-C6 alkenyl group means a linear or branched unsaturated hydrocarbon group having one or more double bonds. When there is a geometric isomer, only one of the E-form and the Z-form, or a mixture of the E-form and the Z-form in an arbitrary ratio is used, and if it is in the range of the specified number of carbon atoms, it is not particularly limited. None. Specific examples of the C2 to C6 alkenyl groups include vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, and 3-pentenyl.
  • C2-C6 haloalkenyl group means a C2-C6 alkenyl group in which a hydrogen atom is arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitution is not particularly limited as long as it can be present as a substituent.
  • C2 to C6 haloalkenyl groups include 2-fluorovinyl, 2,2-difluorovinyl, 2,2-dichlorovinyl, 3-fluoroallyl, 3,3-difluoroallyl, Examples include a 3-dichloroallyl group, a 4,4-difluoro-3-butenyl group, a 5,5-difluoro-4-pentenyl group, and a 6,6-difluoro-5-hexenyl group.
  • the C2-C6 alkynyl group means a linear or branched unsaturated hydrocarbon group having one or more triple bonds.
  • Specific examples of the C2-C6 alkynyl group include ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, and 3-pentynyl.
  • C2-C6 haloalkynyl group means a C2-C6 alkynyl group in which a hydrogen atom is arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitution is not particularly limited as long as it can be present as a substituent.
  • C2-C6 haloalkynyl groups include 2-fluoroethynyl, 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3,3-difluoro-1-propynyl, 3-chloro -3,3-difluoro-1-propynyl group, 3-bromo-3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4-difluoro-1-butynyl Group, 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro-1-butynyl group, 4-chloro-4,4-difluoro-2-butynyl group, 4-bromo-4,4 -Difluoro-1-butynyl group, 4-bromo-4,4-difluoro-2
  • C1 to C6 alkoxy group means a group in which the above C1 to C6 alkyl group is bonded via an oxygen atom.
  • Specific examples of the C1 to C6 alkoxy groups include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, sec-butoxy, t-butoxy, pentyloxy, isopentyloxy, 1-methylbutoxy group, 2-methylbutoxy group, neopentyloxy group, 1-ethylpropyloxy group, 1,2-dimethylpropyloxy group, hexyloxy group, 1-methylpentyloxy group, 2-methylpentyloxy group , 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutoxy, 2,2-dimethylbutoxy, 3,3-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3 -Dimethylbutoxy, 2,3-dimethylbutoxy, 2-ethylbutoxy, 1-is
  • C1 to C6 haloalkoxy group means a group in which a hydrogen atom in the above C1 to C6 alkoxy group is arbitrarily substituted with one or more halogen atoms.
  • those halogen atoms may be the same or different, and the number of substitution is not particularly limited as long as it can be present as a substituent.
  • C1 to C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2 -Trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, pentafluoroethoxy, 2,2,2-trichloroethoxy, 3,3-difluoropropyloxy, 3,3,3-triethoxy Fluoropropyloxy group, heptafluoropropyloxy group, heptafluoroisopropyloxy group, 2,2,2-trifluoro-1- (trifluoromethyl) -ethoxy group, nonafluorobutoxy group, nonafluoro-sec-butoxy group, 3 , 3,4,4,5,5,5-heptafluoropentyloxy group Undecafluoro pentyloxy group, tridecafluoro
  • C3-C8 cycloalkoxy group refers to the above-mentioned C3-C8 cycloalkyl group bonded via an oxygen atom.
  • Specific examples of the C3-C8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy group, and the like.
  • C2-C6 alkenyloxy group means a group in which the above-mentioned C2-C6 alkenyl groups are bonded via an oxygen atom.
  • C2 to C6 alkenyloxy groups include vinyloxy, 1-propenyloxy, allyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-pentenyloxy, and 2-pentenyloxy.
  • C2 to C6 haloalkenyloxy group means a C2 to C6 alkenyloxy group in which a hydrogen atom is arbitrarily substituted by one or more halogen atoms.
  • those halogen atoms may be the same or different, and the number of substitution is not particularly limited as long as it can be present as a substituent.
  • C2 to C6 haloalkenyloxy groups include 2-fluorovinyloxy, 2,2-difluorovinyloxy, 2,2-dichlorovinyloxy, 3-fluoroallyloxy, and 3,3-difluoro Allyloxy group, 3,3-dichloroallyloxy group, 4,4-difluoro-3-butenyloxy group, 5,5-difluoro-4-pentenyloxy group, 6,6-difluoro-5-hexenyloxy group and the like.
  • C3-C6 alkynyloxy group means a C3-C6 alkynyl group bonded to the above-mentioned C2-C6 alkynyl group through an oxygen atom.
  • Specific examples of the C3-C6 alkynyloxy group include propargyloxy, 2-butynyloxy, 3-butynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1,1 -Dimethyl-2-propynyloxy group, 2-hexynyloxy group, 3-hexynyloxy group, 4-hexynyloxy group, 5-hexynyloxy group and the like.
  • C3-C6 haloalkynyloxy group means a group in which a hydrogen atom in the above-mentioned C3-C6 alkynyloxy group is arbitrarily substituted with one or more halogen atoms.
  • those halogen atoms may be the same or different, and the number of substitution is not particularly limited as long as it can be present as a substituent.
  • C3-C6 haloalkynyloxy groups include 1,1-difluoro-2-propynyloxy group, 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro-2-butynyloxy group , 4-bromo-4,4-difluoro-2-butynyloxy group, 4,4,4-trifluoro-2-butynyloxy group, 5,5-difluoro-3-pentynyloxy group, 5-chloro-5,5 -Difluoro-3-pentynyloxy group, 5-bromo-5,5-difluoro-3-pentynyloxy group, 5,5,5-trifluoro-3-pentynyloxy group, 6,6-difluoro-4 -Hexynyloxy group, 6-chloro-6,6-difluoro-4-hexynyloxy group, 6-bromo
  • Aryloxy group means an aryl group such as a phenyl group or a naphthyl group bonded via an oxygen atom. Specific examples of the aryloxy group include a phenoxy group and a naphthyloxy group.
  • Heteroaryloxy groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl
  • a heteroaryl group such as a group, isoxazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, or tetrazolyl group bonded via an oxygen atom.
  • heteroaryloxy group examples include a pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group, a triazinyloxy group, a tetrazinyloxy group, a thienyloxy group, a thiazolyloxy group, and an isothiazolyloxy group.
  • aralkyloxy group refers to an aralkyloxy group in which a hydrogen atom in a C1 to C3 alkyl group is substituted with an aryl group such as a phenyl group or a naphthyl group, via an oxygen atom.
  • aryl group such as a phenyl group or a naphthyl group
  • Specific examples of the aralkyloxy group include a benzyloxy group, a phenethyloxy group, a phenylpropyloxy group, a naphthalenylmethoxy group, a naphthalenylethoxy group, and a naphthalenylpropyloxy group.
  • 3- to 6-membered ring group containing 1 to 2 oxygen atoms include 1,2-epoxyethanyl group, oxetanyl group, oxolanyl group, oxanyl group, 1,3-dioxolanyl group, 1,3- Examples include a dioxanyl group and a 1,4-dioxanyl group.
  • the C2-C6 alkoxyalkoxy group is a C1-C6 alkoxy group in which a hydrogen atom in the C1-C5 alkoxy group is optionally substituted with one or more C1-C5 alkoxy groups.
  • Specific examples of the C2-C6 alkoxyalkoxy groups include methoxymethoxy, ethoxymethoxy, propyloxymethoxy, isopropyloxymethoxy, methoxyethoxy, ethoxyethoxy, propyloxyethoxy, isopropyloxyethoxy, and methoxypropyl. Examples thereof include an oxy group, an ethoxypropyloxy group, a propyloxypropyloxy group, and an isopropyloxypropyloxy group.
  • the pyridone compound of the present invention includes a compound represented by the following formula (1) and a salt thereof (hereinafter, also referred to as “the compound of the present invention”).
  • R1 in the formula (1) is a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, or a C3 to C8 optionally substituted with a substituent A.
  • R1 is a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with a substituent A, A C2-C6 alkenyl group optionally substituted with group A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent A, or a C2-C6 haloalkynyl group;
  • R1 is preferably a C1 to C6 alkyl group or a C1 to C6 haloalkyl group which may be appropriately substituted with the substituent A.
  • RR1 in the formula (1) includes a hydroxyl group and a cyano group.
  • the C1 to C6 alkyl group of the “C1 to C6 alkyl group optionally substituted with the substituent A” for R1 in the formula (1) has the same meaning as described above, and is preferably a methyl group or an ethyl group. Or a propyl group, and more preferably a methyl group or an ethyl group.
  • the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent A.
  • the “C1 to C6 haloalkyl group” for R1 in the formula (1) is as defined above, and is preferably a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoro group.
  • the C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with substituent A" for R1 in formula (1) has the same meaning as defined above, and is preferably a cyclopropyl group. , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group.
  • the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent A.
  • the C2 to C6 alkenyl group of the “C2 to C6 alkenyl group optionally substituted with the substituent A” for R1 in the formula (1) has the same meaning as described above, and is preferably a vinyl group, 1- It is a propenyl group or an allyl group, and more preferably a vinyl group or an allyl group.
  • the hydrogen atom in the alkenyl group of C2 to C6 is optionally substituted by the substituent A.
  • the “C2-C6 haloalkenyl group” for R1 in the formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or It is a 3,3-difluoroallyl group, more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.
  • the C2 to C6 alkynyl group of the “C2 to C6 alkynyl group optionally substituted with the substituent A” for R1 in the formula (1) has the same meaning as defined above, and is preferably a propargyl group, It is a butynyl group or a 3-butynyl group, more preferably a propargyl group.
  • the hydrogen atom in the C2 to C6 alkynyl group is optionally substituted by the substituent A.
  • the “C2-C6 haloalkynyl group” for R1 in the formula (1) has the same meaning as defined above, and is preferably a 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro- A 2-butynyl group, a 4-bromo-4,4-difluoro-2-butynyl group or a 4,4,4-trifluoro-2-butynyl group, more preferably 4,4-difluoro-2-butynyl Or a 4,4,4-trifluoro-2-butynyl group.
  • the C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with the substituent A" for R1 in the formula (1) has the same meaning as described above, and is preferably a methoxy group or an ethoxy group. Or a propyloxy group, and more preferably a methoxy group or an ethoxy group.
  • the hydrogen atom in the C1 to C6 alkoxy group is optionally substituted by the substituent A.
  • the “C1 to C6 haloalkoxy group” for R1 in the formula (1) is as defined above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2 A 2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, or a 3,3,3-trifluoropropyloxy group, more preferably a difluoromethoxy group, a trifluoromethoxy group, or a 2,2-difluoroethoxy group; Or 2,2,2-trifluoroethoxy group.
  • the C3-C8 cycloalkoxy group of the "C3-C8 cycloalkoxy group optionally substituted with substituent A" for R1 in formula (1) has the same meaning as defined above, and is preferably cyclopropyloxy.
  • the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent A.
  • the C2 to C6 alkenyloxy group of the "C2 to C6 alkenyloxy group optionally substituted with the substituent A" for R1 in the formula (1) has the same meaning as described above, and is preferably a vinyloxy group, It is a 1-propenyloxy group or an allyloxy group, and more preferably a vinyloxy group.
  • the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent A.
  • the “C2-C6 haloalkenyloxy group” in R1 of the formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 3-fluoro An allyloxy group or a 3,3-difluoroallyloxy group, more preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.
  • the C3 to C6 alkynyloxy group of the "C3 to C6 alkynyloxy group optionally substituted with the substituent A" for R1 in the formula (1) has the same meaning as defined above, and is preferably a propargyloxy group , A 2-butynyloxy group or a 3-butynyloxy group, and more preferably a propargyloxy group.
  • the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted by the substituent A.
  • the “C3-C6 haloalkynyloxy group” in R1 of the formula (1) has the same meaning as defined above, and is preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4- A difluoro-2-butynyloxy group, a 4-bromo-4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2 —Butynyloxy group or 4,4,4-trifluoro-2-butynyloxy group.
  • Ra and RbN- in R1 of the formula (1) (where Ra and Rb are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 Represents a haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb, together with the nitrogen atom to which they are attached, represent an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group; Each term is the same as defined above.
  • RaRbN- preferably, an amino group, a methylamino group, an ethylamino group, a (methoxymethyl) amino group, a (2-methoxyethyl) amino group, a (cyanomethyl) amino group, a (2-cyanoethyl) amino group, Dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, 2,2- A difluoroethylamino group, a 2,2,2-trifluoroe
  • R2, R3 and R4 in the formula (1) are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent C, A C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, A C2-C6 alkynyl group optionally substituted with a substituent C, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent C, a C1-C6 haloalkoxy group, A C3-C8 cycloalkoxy group optionally substituted with a substituent C, a C2-C6 alkeny
  • RaRbN- where Ra and Rb are as defined above
  • Rx2C O) N (Rx3)-(where Rx2 is a hydrogen atom or a substituent B C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (Where Ra and Rb are as defined above), and Rx3 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or C A cycloalkyl group of ⁇ C8. ).
  • R2, R3 and R4 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, A C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 alkynyl group optionally substituted with a substituent C, and a C1-C6 alkoxy group optionally substituted with a substituent C , A C1-C6 haloalkoxy group, a C2-C6 alkenyloxy group optionally substituted with a substituent C, a C2-C6 haloalkenyloxy group, a C3-C6 optionally substituted with a substituent C An alkynyloxy group, a C3-C6 haloalkynyloxy group, an aralkyloxy group optionally substitute
  • RR2 in the formula (1) includes a hydrogen atom, a hydroxyl group, a cyano group, and a nitro group.
  • the halogen atom for R2 in the formula (1) is as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
  • the C1 to C6 alkyl group of the “C1 to C6 alkyl group optionally substituted with a substituent C” in R2 of the formula (1) has the same meaning as described above, and is preferably a methyl group or an ethyl group.
  • the hydrogen atom in the C1 to C6 alkyl group is optionally substituted by the substituent C.
  • the “C1 to C6 haloalkyl group” for R2 in the formula (1) is as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, or a 2,2,2 It is a 2-trifluoroethyl group, and more preferably a difluoromethyl group or a trifluoromethyl group.
  • the C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with a substituent C" for R2 in formula (1) has the same meaning as defined above, and is preferably a cyclopropyl group. , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group.
  • the hydrogen atom in the C3 to C8 cycloalkyl group is optionally substituted by the substituent C.
  • the C2-C6 alkenyl group of the "C2-C6 alkenyl group optionally substituted with substituent C" for R2 in formula (1) has the same meaning as defined above, and is preferably a vinyl group, 1- It is a propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group or an allyl group.
  • the hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent C.
  • the “C2-C6 haloalkenyl group” for R2 in the formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group. , A 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 3,3-dichloroallyl group, and more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.
  • the C2 to C6 alkynyl groups in the “C2 to C6 alkynyl groups optionally substituted with the substituent C” in R2 of the formula (1) are as defined above, and are preferably ethynyl group, 1- A propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, and more preferably an ethynyl group, a 1-propynyl group, or a propargyl group;
  • the hydrogen atom in the alkynyl group of C2 to C6 is optionally substituted by the substituent C.
  • the “C2-C6 haloalkynyl group” in R2 of the formula (1) has the same meaning as defined above, and is preferably a 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -Propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- It is a 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.
  • the C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with a substituent C" in R2 of the formula (1) has the same meaning as described above, and is preferably a methoxy group or an ethoxy group.
  • the hydrogen atom in the C1-C6 alkoxy group is optionally substituted by the substituent C.
  • the “C1 to C6 haloalkoxy group” for R2 in the formula (1) is as defined above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2 A 2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, or a 3,3,3-trifluoropropyloxy group, more preferably a difluoromethoxy group, a trifluoromethoxy group, or a 2,2-difluoroethoxy group; Or 2,2,2-trifluoroethoxy group.
  • the C3-C8 cycloalkoxy group of the "C3-C8 cycloalkoxy group optionally substituted with substituent C" for R2 in formula (1) has the same meaning as defined above, and is preferably cyclopropyloxy.
  • the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent C.
  • the C2 to C6 alkenyloxy group of the “C2 to C6 alkenyloxy group optionally substituted with the substituent C” for R2 in the formula (1) is the same as defined above, and is preferably a vinyloxy group, A 1-propenyloxy group, an allyloxy group, a 1-butenyloxy group, a 2-butenyloxy group, or a 3-butenyloxy group is more preferable, and a vinyloxy group, a 1-propenyloxy group, or an allyloxy group is more preferable.
  • the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent C.
  • the “C2-C6 haloalkenyloxy group” for R2 in the formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2- A dichlorovinyloxy group, a 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group or a 3,3-dichloroallyloxy group, more preferably a 2-fluorovinyloxy group or a 2,2-difluoro It is a vinyloxy group.
  • the C3-C6 alkynyloxy group of the "C3-C6 alkynyloxy group optionally substituted with the substituent C" for R2 in the formula (1) has the same meaning as defined above, and is preferably a propargyloxy group , A 2-butynyloxy group or a 3-butynyloxy group, and more preferably a propargyloxy group or a 2-butynyloxy group.
  • a hydrogen atom in the C3 to C6 alkynyloxy group is optionally substituted by the substituent C.
  • the “C3-C6 haloalkynyloxy group” in R2 of the formula (1) has the same meaning as defined above, and is preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- A butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.
  • the aryloxy group of the “aryloxy group optionally substituted with 0 to 5 substituents D” in R2 of the formula (1) has the same meaning as described above, and is preferably a phenoxy group or a naphthyloxy group. And more preferably a phenoxy group.
  • the hydrogen atom in the aryloxy group is optionally substituted by the substituent D.
  • each is independent.
  • the heteroaryloxy group of the “heteroaryloxy group optionally substituted with 0 to 2 substituent (s) D” for R 2 in formula (1) has the same meaning as defined above, and is preferably a pyridyloxy group, a pyridyl group, Dinyloxy group, pyrimidinyloxy group, pyrazinyloxy group, triazinyloxy group, tetrazinyloxy group, thienyloxy group, thiazolyloxy group, isothiazolyloxy group, or thiadiazolyloxy group, more preferably, A pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, or a pyrazinyloxy group.
  • a hydrogen atom in the heteroaryloxy group is optionally substituted by the substituent D.
  • each is independent.
  • the aralkyloxy group of the “aralkyloxy group optionally substituted with 0 to 5 substituents D” in R2 of the formula (1) is as defined above, and is preferably a benzyloxy group, a phenethyloxy group, Or a phenylpropyloxy group, more preferably a benzyloxy group or a phenethyloxy group.
  • the hydrogen atom in the aralkyloxy group is optionally substituted by the substituent D.
  • each is independent.
  • Rx1 is preferably a C1-C6 alkyl group optionally substituted with a substituent B, or a C1-C6 alkoxy group, and more preferably C1-C6 optionally substituted with a substituent B. Is an alkyl group.
  • Rx1 is preferably a C1-C6 alkyl group optionally substituted with a substituent B, or a C1-C6 alkoxy group, and more preferably C1-C6 optionally substituted with a substituent B. Is an alkyl group.
  • the “3- to 6-membered ring group containing 1 or 2 oxygen atoms” in R 2 of the formula (1) is as defined above, and is preferably an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group. Or a 1,3-dioxanyl group, and more preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.
  • Rc-L - in R2 of formula (1) (wherein, Rc represents a haloalkyl group of alkyl or C1 ⁇ C6 of C1 ⁇ C6, L represents S, SO, or SO 2.)
  • Rc-L- is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group Or a methanesulfonyl group.
  • Ra and Rb of "RaRbN-" in R2 of the formula (1) are as defined above.
  • RaRbN- preferably, an amino group, a methylamino group, an ethylamino group, a (methoxymethyl) amino group, a (2-methoxyethyl) amino group, a (cyanomethyl) amino group, a (2-cyanoethyl) amino group, Dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, 2,2- A difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl) methylamino group,
  • C1 to C6 alkyl group optionally substituted with a substituent B when the compound has a substituent B, a hydrogen atom in the C1 to C6 alkyl group may be optionally selected depending on the substituent B.
  • Is replaced by Rx2 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a difluoromethyl group, a trifluoromethyl group, a cyclopropyl group, a methoxy group, an ethoxy group, a 2,2-difluoroethoxy, 2,2-trifluoroethoxy, cyclopropyloxy, amino, methylamino, ethylamino, (methoxymethyl) amino, (2-methoxyethyl) amino, (cyanomethyl) amino, (2- (Cyanoethyl) amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl)
  • Rx3 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-cyanoethyl group, a propyl group, A 2-difluoroethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropyl group, more preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, It is a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.
  • RR3 in the formula (1) has the same meaning as R2 described above.
  • RR4 in the formula (1) has the same meaning as R2 described above.
  • RR2, R3 and R4 in the formula (1) are each independent and may be the same or different and are not particularly limited.
  • R5 in the formula (1) is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a substituent A optionally substituted.
  • C3-C8 cycloalkyl group which may be optionally substituted, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 haloalkenyl group, C2-C6 optionally substituted with substituent A
  • R5 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent A.
  • An oxy group, a C3-C6 alkynyloxy group optionally substituted with a substituent A, or R51C ( O)-(where R51 is a hydroxyl group or a C1-C6 optionally substituted with a substituent B)
  • R5 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a C2-C6 alkynyl optionally substituted with
  • RR5 in the formula (1) includes a hydrogen atom, a cyano group, and a nitro group.
  • the halogen atom for R5 in the formula (1) has the same meaning as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
  • the C1 to C6 alkyl group of the “C1 to C6 alkyl group optionally substituted with the substituent A” for R5 in the formula (1) is the same as defined above, and is preferably a methyl group or an ethyl group.
  • the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent A.
  • the “C1 to C6 haloalkyl group” for R5 in the formula (1) is as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2 A trifluoroethyl group, a 3,3-difluoropropyl group or a 3,3,3-trifluoropropyl group, more preferably a difluoromethyl group or a trifluoromethyl group.
  • the C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with substituent A" for R5 in the formula (1) is as defined above, and is preferably a cyclopropyl group. , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group.
  • the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent A.
  • the C2 to C6 alkenyl group of the “C2 to C6 alkenyl group optionally substituted with the substituent A” in R5 of the formula (1) has the same meaning as described above, and is preferably a vinyl group, 1- It is a propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group or an allyl group.
  • the hydrogen atom in the alkenyl group of C2 to C6 is optionally substituted by the substituent A.
  • the “C2-C6 haloalkenyl group” for R5 in the formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group. , A 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 3,3-dichloroallyl group, and more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.
  • the C2 to C6 alkynyl group of the “C2 to C6 alkynyl group optionally substituted with the substituent A” for R5 in the formula (1) has the same meaning as described above, and is preferably an ethynyl group, 1- A propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, and more preferably an ethynyl group, a 1-propynyl group, or a propargyl group;
  • the hydrogen atom in the C2 to C6 alkynyl group is optionally substituted by the substituent A.
  • the “C2-C6 haloalkynyl group” in R5 of the formula (1) is as defined above, and is preferably a 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -Propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- It is a 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.
  • the C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with the substituent A" in R5 of the formula (1) has the same meaning as described above, and is preferably a methoxy group or an ethoxy group.
  • the hydrogen atom in the C1 to C6 alkoxy group is optionally substituted by the substituent A.
  • the “C1 to C6 haloalkoxy group” for R5 in the formula (1) is as defined above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2 A 2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, or a 3,3,3-trifluoropropyloxy group, more preferably a difluoromethoxy group, a trifluoromethoxy group, or a 2,2-difluoroethoxy group; Or 2,2,2-trifluoroethoxy group.
  • the C3-C8 cycloalkoxy group of the "C3-C8 cycloalkoxy group optionally substituted with substituent A" for R5 in formula (1) has the same meaning as defined above, and is preferably cyclopropyloxy.
  • the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent A.
  • the C2-C6 alkenyloxy group of the “C2-C6 alkenyloxy group optionally substituted with the substituent A” for R5 in the formula (1) has the same meaning as defined above, and is preferably a vinyloxy group, A 1-propenyloxy group, an allyloxy group, a 1-butenyloxy group, a 2-butenyloxy group, or a 3-butenyloxy group is more preferable, and a vinyloxy group, a 1-propenyloxy group, or an allyloxy group is more preferable.
  • the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent A.
  • the “C2 to C6 haloalkenyloxy group” for R5 in the formula (1) is as defined above, and is a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2-dichlorovinyloxy group.
  • the C3-C6 alkynyloxy group of the "C3-C6 alkynyloxy group optionally substituted with the substituent A" for R5 in the formula (1) has the same meaning as defined above, and is preferably a propargyloxy group , A 2-butynyloxy group or a 3-butynyloxy group, and more preferably a propargyloxy group.
  • the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted by the substituent A.
  • the “C3-C6 haloalkynyloxy group” for R5 in the formula (1) is as defined above, and preferably is a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro group.
  • -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group or 4,4,4-trifluoro-2-butynyloxy group more preferably 4,4-difluoro-2- A butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.
  • Rc-L- is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group Or a methanesulfonyl group.
  • Ra and Rb of "RaRbN-" in R5 of the formula (1) are as defined above.
  • RaRbN- preferably, an amino group, a methylamino group, an ethylamino group, a (methoxymethyl) amino group, a (2-methoxyethyl) amino group, a (cyanomethyl) amino group, a (2-cyanoethyl) amino group, Dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, 2,2- A difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl) methylamino group,
  • R51 is a hydroxyl group, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C3 to Each of which represents a cycloalkyl group of C8 or an alkoxy group of C1 to C6
  • C1 to C6 alkyl group optionally substituted with the substituent B when the compound has the substituent B, a hydrogen atom in the C1 to C6 alkyl group is optionally substituted by the substituent B. .
  • R51 is preferably a C1 to C6 alkyl group optionally substituted with a substituent B.
  • X in the formula (1) represents an oxygen atom or a sulfur atom.
  • Preferred X is an oxygen atom.
  • Y is the formula (y-1) or the formula (y-2) Represents
  • R6 is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, or a C3 to C3 optionally substituted with a substituent C.
  • R6 is a halogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, or a C2 to C6 optionally substituted with a substituent C.
  • Rc-L- (wherein, Rc represents a C1 ⁇ C6 alkyl group or a C1 ⁇ C6 haloalkyl group, L is, S, SO or an SO 2,.), or RaRbN- (here , Ra and Rb are as defined above).
  • R6 is a halogen atom, a cyano group, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, or a C1-C6 alkoxy optionally substituted with a substituent C. Groups are preferred.
  • the halogen atom in R6 of the formula (1) has the same meaning as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
  • RR6 in the formula (1) includes a hydroxyl group, a cyano group, and a nitro group.
  • the C1 to C6 alkyl group of the “C1 to C6 alkyl group optionally substituted with a substituent C” for R6 in the formula (1) has the same meaning as defined above, and is preferably a methyl group or an ethyl group. Or a propyl group, and more preferably a methyl group or an ethyl group.
  • the hydrogen atom in the C1 to C6 alkyl group is optionally substituted by the substituent C.
  • the “C1 to C6 haloalkyl group” for R6 in the formula (1) is as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2 A trifluoroethyl group, a 3,3-difluoropropyl group or a 3,3,3-trifluoropropyl group, more preferably a difluoromethyl group or a trifluoromethyl group.
  • the C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with a substituent C" for R6 in formula (1) has the same meaning as defined above, and is preferably a cyclopropyl group. , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group.
  • the hydrogen atom in the C3 to C8 cycloalkyl group is optionally substituted by the substituent C.
  • the C2 to C6 alkenyl group of the “C2 to C6 alkenyl group optionally substituted by substituent C” for R6 in the formula (1) has the same meaning as described above, and is preferably a vinyl group, 1- It is a propenyl group or an allyl group, and more preferably a vinyl group.
  • the hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent C.
  • the “C2 to C6 haloalkenyl group” for R6 in the formula (1) is as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group. , A 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 3,3-dichloroallyl group, and more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.
  • the C2 to C6 alkynyl groups of the “C2 to C6 alkynyl groups optionally substituted with the substituent C” for R6 in the formula (1) have the same meaning as described above, and are preferably an ethynyl group, 1- A propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, and more preferably an ethynyl group, a 1-propynyl group, or a propargyl group;
  • the hydrogen atom in the alkynyl group of C2 to C6 is optionally substituted by the substituent C.
  • the “C2-C6 haloalkynyl group” in R6 of the formula (1) has the same meaning as defined above, and is preferably a 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -Propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- It is a 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.
  • the C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with the substituent C" for R6 in the formula (1) has the same meaning as described above, and is preferably a methoxy group or an ethoxy group.
  • the hydrogen atom in the C1-C6 alkoxy group is optionally substituted by the substituent C.
  • the “C1 to C6 haloalkoxy group” for R6 in the formula (1) is as defined above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2 A 2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, or a 3,3,3-trifluoropropyloxy group, more preferably a difluoromethoxy group or a trifluoromethoxy group
  • the C3-C8 cycloalkoxy group of the “C3-C8 cycloalkoxy group optionally substituted with substituent C” for R6 in formula (1) has the same meaning as defined above, and is preferably cyclopropyloxy.
  • the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent C.
  • the C2 to C6 alkenyloxy group of the “C2 to C6 alkenyloxy group optionally substituted with the substituent C” for R6 in the formula (1) has the same meaning as defined above, and is preferably a vinyloxy group, A 1-propenyloxy group or an allyloxy group, more preferably a vinyloxy group.
  • the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent C.
  • the “C2-C6 haloalkenyloxy group” for R6 in the formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2- A dichlorovinyloxy group, a 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group or a 3,3-dichloroallyloxy group, more preferably a 2-fluorovinyloxy group or a 2,2-difluoro It is a vinyloxy group.
  • the C3 to C6 alkynyloxy group of the "C3 to C6 alkynyloxy group optionally substituted with the substituent C" for R6 in the formula (1) is as defined above, and is preferably a propargyloxy group , A 2-butynyloxy group or a 3-butynyloxy group, and more preferably a propargyloxy group.
  • a hydrogen atom in the C3 to C6 alkynyloxy group is optionally substituted by the substituent C.
  • the “C3-C6 haloalkynyloxy group” in R6 of the formula (1) has the same meaning as defined above, and is preferably a 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- A butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.
  • the aryloxy group of the “aryloxy group optionally substituted with 0 to 5 substituent (s) D” in R6 of the formula (1) is as defined above, and is preferably a phenoxy group or a naphthyloxy group. And more preferably a phenoxy group.
  • the hydrogen atom in the aryloxy group is optionally substituted by the substituent D.
  • each is independent.
  • the heteroaryloxy group of the “heteroaryloxy group optionally substituted with 0 to 2 substituent (s) D” for R 6 in the formula (1) is as defined above, and is preferably a pyridyloxy group or a pyridyl group. Dinyloxy group, pyrimidinyloxy group, pyrazinyloxy group, triazinyloxy group, tetrazinyloxy group, thienyloxy group, thiazolyloxy group, isothiazolyloxy group, thiadiazolyloxy group, more preferably pyridyl Oxy, pyridazinyloxy, pyrimidinyloxy and pyrazinyloxy groups.
  • a hydrogen atom in the heteroaryloxy group is optionally substituted by the substituent D.
  • each is independent.
  • the aralkyloxy group of the “aralkyloxy group optionally substituted with 0 to 5 substituents D” in R6 of the formula (1) has the same meaning as described above, and is preferably a benzyloxy group, a phenethyloxy group, It is a phenylpropyloxy group, more preferably a benzyloxy group and a phenethyloxy group.
  • the hydrogen atom in the aralkyloxy group is optionally substituted by the substituent D.
  • each is independent.
  • Rx1 is preferably a C1 to C6 alkyl group or a C1 to C6 alkoxy group which may be appropriately substituted with the substituent B.
  • Rx1 is preferably a C1 to C6 alkyl group or a C1 to C6 alkoxy group which may be appropriately substituted with the substituent B.
  • the “3- to 6-membered ring group containing 1 or 2 oxygen atoms” in R 6 of the formula (1) is as defined above, and is preferably an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group. Or a 1,3-dioxanyl group, and more preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.
  • Rc-L- is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group Or a methanesulfonyl group.
  • Ra and Rb of "RaRbN-" in R6 of the formula (1) are as defined above.
  • RaRbN- preferably, an amino group, a methylamino group, an ethylamino group, a (methoxymethyl) amino group, a (2-methoxyethyl) amino group, a (cyanomethyl) amino group, a (2-cyanoethyl) amino group, Dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, 2,2- A difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl) methylamino group,
  • Rx2 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a difluoromethyl group, a trifluoromethyl group, a cyclopropyl group, a methoxy group, an ethoxy group, a 2,2-difluoroethoxy, 2,2-trifluoroethoxy, cyclopropyloxy, amino, methylamino, ethylamino, (methoxymethyl) amino, (2-methoxyethyl) amino, (cyanomethyl) amino, (2- (Cyanoethyl) amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-meth
  • Rx3 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-cyanoethyl group, a propyl group, A 2-difluoroethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropyl group, more preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, It is a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.
  • Y is the formula (y-1) Represents a partial structure represented by
  • RR6 in formula (y-1) has the same meaning as described above.
  • N n in the formula (y-1) represents an integer of 0 to 3.
  • n in the formula (y-1) is 2 or more, two or more R6s each represent an independent substituent, which may be the same or different, and can be arbitrarily selected.
  • Y is the formula (y-2) Represents a partial structure represented by
  • RR6 in the formula (y-2) has the same meaning as described above.
  • N n in the formula (y-2) represents an integer of 0 to 3.
  • n in the formula (y-2) is 2 or more, two or more R6s each represent an independent substituent, which may be the same or different, and can be arbitrarily selected.
  • the bond including the broken line part in the equation (1) is Represents a portion represented by.
  • the bond containing the broken line in Formula (1) represents a double bond or a single bond.
  • a preferable bond containing a broken line is a double bond.
  • R5 in the formula (1b) is a substituent other than hydrogen, it is either the R-form or the S-form alone, or a mixture of the R-form and the S-form at an arbitrary ratio.
  • the compound represented by the formula (1) may have one or two axial asymmetries.
  • the isomer ratio at this time is a single ratio or a mixing ratio of an arbitrary ratio, and is not particularly limited.
  • the compound represented by the formula (1) may contain an asymmetric atom.
  • the isomer ratio at this time is a single ratio or a mixing ratio of an arbitrary ratio, and is not particularly limited.
  • the compound represented by the formula (1) may include a geometric isomer.
  • the isomer ratio at this time is a single ratio or a mixing ratio of an arbitrary ratio, and is not particularly limited.
  • the compound represented by the formula (1) may form a salt in some cases.
  • Acid salts such as hydrochloric acid, sulfuric acid, acetic acid, fumaric acid, and maleic acid, and metal salts such as sodium, potassium, and calcium are exemplified, but are not particularly limited as long as they can be used as agricultural and horticultural fungicides. There is no.
  • the “substituent A” in the formula (1) includes a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a RaRbN- (Here, Ra and Rb have the same meanings as described above.) And Rc-L- (where Rc and L have the same meanings as described above).
  • the substituent A is preferably a cyano group, a C1 to C6 alkoxy group or Rc-L- (where Rc and L are as defined above), Particularly, a cyano group or a C1 to C6 alkoxy group is preferable.
  • substituent A a hydroxyl group; a cyano group; C3-C8 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; A C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group; C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group; A C3-C8 cycloalkoxy group such as a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group; RaRbN- (
  • substituent A a hydroxyl group; a cyano group; A C3-C8 cycloalkyl group such as a cyclopropyl group and a cyclobutyl group; A methoxy group and an ethoxy group as the C1-C6 alkoxy group; A C1-C6 haloalkoxy group such as a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group; A C3-C8 cycloalkoxy group such as a cyclopropyloxy group and a cyclobutoxy group; RaRbN- (where Ra and Rb are as defined above), such as a dimethylamino group, an ethylmethylamino group, and a diethylamino group; And Rc-L- (where Rc and L have the same meanings as described above) include
  • Substituent B represents at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group.
  • the substituent B is preferably a cyano group or a C1 to C6 alkoxy group.
  • substituent B a cyano group
  • a C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group
  • C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group
  • C3-C8 cycloalkoxy groups include cyclopropyloxy, cyclobutoxy, cyclopentyloxy, and cyclohexyloxy groups.
  • substituent B a cyano group; A methoxy group and an ethoxy group as the C1-C6 alkoxy group; A C1-C6 haloalkoxy group such as a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group; And the C3-C8 cycloalkoxy group includes a cyclopropyloxy group and a cyclobutoxy group.
  • a cyano group, a C1-C6 alkoxy group, Rc-L- (where Rc and L are as defined above) or a 3- to 6-membered ring group containing 1-2 oxygen atoms is preferred. preferable.
  • substituent C a hydroxyl group; a cyano group; C3-C8 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
  • a C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, and a t-butoxy group;
  • C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
  • a C3-C8 cycloalkoxy group such as a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyl
  • substituent C a hydroxyl group; a cyano group; A C3-C8 cycloalkyl group such as a cyclopropyl group and a cyclobutyl group; A methoxy group and an ethoxy group as the C1-C6 alkoxy group; A C1-C6 haloalkoxy group such as a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group; A C3-C8 cycloalkoxy group such as a cyclopropyloxy group or a cyclobutoxy group; A C2-C6 alkoxyalkoxy group such as a methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, and an ethoxyethoxy group; RaRbN- (where Ra and Rb are as defined above), such as
  • the “substituent D” in the formula (1) includes a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C6 It represents at least one selected from the group consisting of a C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group and a C3 to C8 cycloalkoxy group.
  • the substituent D is a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group or a C1-C6 haloalkoxy group which may be appropriately substituted with the substituent B.
  • a halogen atom or a C1 to C6 haloalkyl group is preferable.
  • substituent D are as defined above.
  • the hydrogen atom in the C1 to C6 alkyl group is optional depending on the substituent B. Is replaced by
  • substituent D As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; Hydroxyl group; cyano group; nitro group;
  • substituent B examples of the C1-C6 alkyl group optionally substituted with the substituent B include a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, and a 2-cyanoethyl group.
  • C1-C6 haloalkyl groups include difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3-difluoropropyl, and 3,3,3 A trifluoropropyl group;
  • C3-C8 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
  • a C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, and a t-butoxy group;
  • C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoro
  • substituent D As a halogen atom, a fluorine atom, a chlorine atom, and a bromine atom; Hydroxyl group; cyano group; nitro group;
  • substituent B examples of the C1-C6 alkyl group optionally substituted with the substituent B include a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, and a 2-alkyl group.
  • specific compounds of the present invention include structural formulas (P-1 to P-616) shown in Table 1, Y (Y-1 to Y-910) shown in Table 2, an oxygen atom or a sulfur atom. Is represented by a combination with X. These compounds are for illustration only and the invention is not limited thereto.
  • the description “2-Thio” in Table 2 represents a thiophen-2-yl group bonded to the pyridone ring portion of the formula (1) at the 2-position
  • the description “3-Thio” Represents a thiophen-3-yl group bonded to the pyridone ring moiety of the formula (1) at the 3-position.
  • 2-F-3-Tio means a thiophen-3-yl group having a fluorine atom bonded to the 2-position
  • 4-Cl-5-F-3-Tio Means a thiophen-3-yl group in which a chlorine atom is bonded to the 4-position and a fluorine atom is bonded to the 5-position
  • 2,4-di-F-3-Thio Means a thiophen-3-yl group having a fluorine atom bonded to the 2-position and 4-position, and the same applies to other descriptions.
  • the production method of the compound of the present invention is not limited to Production Methods A to V.
  • R9 represents a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, or a C3 to C3 optionally substituted with a substituent A.
  • Production method A is a method for obtaining a compound represented by the formula containing a preparation intermediate of the compound of the present invention and the present invention compound (1b-a), a compound R9NH 2 represented by the formula (3) A reaction in the presence of an acid.
  • R9NH 2 used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • R9NH 2 are hydrochloric, may be those forming a salt with an acidic compound such as acetic acid, it is not particularly limited as long as the reaction proceeds to the desired.
  • R9NH 2 used in this reaction may be at least 1 equivalent to the compound represented by the formula (3), and is not particularly limited as long as the desired reaction proceeds. It is equal to or more than 200 equivalents.
  • Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, methanesulfonic acid and p-toluenesulfonic acid, and are not particularly limited as long as the desired reaction proceeds. But not preferably acetic acid. Further, when using salts of R9NH 2 and the acidic compound, the use of acid is not essential.
  • the amount of the acid used in this reaction may be 1 equivalent or more relative to R9NH 2 and is not particularly limited as long as the desired reaction proceeds, but is preferably 1 equivalent to 200 equivalents. is there.
  • the acid used is a liquid, it can be used as a solvent.
  • a solvent can be used for this reaction, but it is not essential.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but acidic solvents such as acetic acid and methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxy Ether solvents such as ethane, tetrahydrofuran and dioxane; alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ethyl acetate, isopropyl acetate and butyl acetate; Ester solvents, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, and urea solvents such as 1,3-dimethyl-2-
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (3). is there.
  • the temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 50 ° C or higher and 180 ° C or lower or the boiling point of the solvent or lower.
  • liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
  • reaction mixture containing the compound represented by the formula (1ba) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • reaction mixture containing the compound represented by the formula (1ba) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (1ba) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • the compound represented by the formula (2) that can be produced when R9 represents a hydrogen atom in the compound represented by the formula (1ba) is a compound of the formula (1) It can be a useful production intermediate for obtaining the compound represented by 1b).
  • Specific examples of the production intermediate represented by the formula (2) include structural formulas (I-1 to I-154) shown in Table 3, Y (Y-1 to Y-910) shown in Table 2, and oxygen It is represented by a combination with an atom or a sulfur atom X. These compounds are for illustration only and the invention is not limited thereto.
  • Lv represents a leaving group such as a methanesulfonyl group, a trifluoromethanesulfonyl group, a p-toluenesulfonyl group, a halogen atom and the like, and R1, R2, R3, R4, R5, X and Y are as defined above. .
  • the production method B is a method for obtaining a compound represented by the formula (1b), and comprises reacting the production intermediate represented by the formula (2) with R1Lv in a solvent in the presence of a base. It is a manufacturing method.
  • RR1Lv used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • the amount of R1Lv used in this reaction may be 1 equivalent or more based on the compound represented by the formula (2), and is not particularly limited as long as the desired reaction proceeds. It is 1 equivalent or more and 10 equivalents or less.
  • Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride, but are not particularly limited as long as the desired reaction proceeds. It will not be done.
  • the amount of the base used in this reaction may be one equivalent or more based on the compound represented by the formula (2), and is not particularly limited as long as the desired reaction proceeds. It is 1 equivalent or more and 10 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; Alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; Amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane,
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (2). is there.
  • the temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 0 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
  • liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved
  • an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved
  • thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
  • reaction mixture containing the compound represented by the formula (1b) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • reaction mixture containing the compound represented by the formula (1b) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by formula (1b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • SR represents a sulfurizing agent
  • R1, R2, R3, R4, R5 and Y are as defined above.
  • the production method C is a production method for obtaining a compound represented by the formula (1bc) among the compounds represented by the formula (1b), wherein the compound represented by the formula (1bb) is A production method comprising reacting an agent (SR) in a solvent.
  • SR agent
  • Examples of the sulfurizing agent used in this reaction include Lawesson's reagent (2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetane-2,4-disulfide).
  • the amount of the sulfurizing agent used in this reaction may be at least 0.5 equivalent to the compound represented by the formula (1bb), and is not particularly limited as long as the desired reaction proceeds. However, it is preferably 1 equivalent or more and 10 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; Benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene are exemplified. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
  • ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane
  • Benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually at least 3 times by weight to 200 times by weight the compound represented by the formula (1bb). It is as follows.
  • the temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 50 ° C or higher and 180 ° C or lower or the boiling point of the solvent or lower.
  • a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane.
  • ether solvents such as t-butyl ether
  • halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride
  • hydrocarbon solvents such as hexane, heptane,
  • these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
  • the number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. In this reaction, a liquid separation operation is not essential.
  • reaction mixture containing the compound represented by the formula (1bc) can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • reaction mixture containing the compound represented by the formula (1bc) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (1bc) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • R5a is a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A
  • a substituent A represents a C2-C6 alkenyl group optionally substituted with A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with the substituent A, or a C2-C6 haloalkynyl group.
  • R1, R2, R3, R4, Lv, X and Y are as defined above.
  • R5a is an alkyl group of C1 to C6, a haloalkyl group of C1 to C6, and a substituent A which are optionally substituted with a substituent A.
  • a C3-C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 optionally substituted with a substituent A A method for synthesizing a compound represented by the formula (1b-e) which is an alkynyl group or a C2 to C6 haloalkynyl group, wherein the compound represented by the formula (1b-d) and R5aLv are linked to the presence of a base.
  • the following is a production method including reacting in a solvent.
  • RR5aLv used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • the amount of R5aLv used in this reaction may be at least 1 equivalent to the compound represented by the formula (1b-d), and is not particularly limited as long as the desired reaction proceeds, but is preferably Is not less than 1 equivalent and not more than 1.8 equivalents.
  • metal hydrides such as sodium hydride, organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, hexyllithium, lithium diisopropylamide, hexamethyldisilazane
  • metal amides such as lithium, sodium hexamethyldisilazane, and potassium hexamethyldisilazane are exemplified.
  • the amount of the base used in this reaction may be at least 1 equivalent to the compound represented by the formula (1b-d), and is not particularly limited as long as the desired reaction proceeds, but is preferably Is 1 equivalent or more and 10 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane;
  • ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane
  • benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene
  • hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane.
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually at least 3 times by weight to 200 times by weight the compound represented by the formula (1b-d). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually ⁇ 80 ° C. or more and 100 ° C. or less or the boiling point of the solvent or less.
  • liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, etc. are dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. are dissolved, sodium thiosulfate, sulfurous acid
  • An aqueous solution or a salt solution in which a salt containing a sulfur atom such as sodium is dissolved can be arbitrarily used.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane and chloroform, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, may be added. It is possible. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
  • reaction mixture containing the compound represented by the formula (1be) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • reaction mixture containing the compound represented by the formula (1be) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (1be) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • Ox represents an oxidizing agent
  • R1, R2, R3, R4, R5, X and Y are as defined above.
  • the production method E is a method for obtaining a compound represented by the formula (1a), and comprises reacting a compound represented by the formula (1b) with an oxidizing agent (Ox) in a solvent. is there.
  • the oxidizing agent used in this reaction includes metal oxides such as manganese dioxide, benzoquinones such as 2,3-dichloro-5,6-dicyano-p-benzoquinone, azobisisobutyronitrile, benzoyl peroxide and the like.
  • a combination with a halogenating agent such as diiodo-5,5-dimethylhydantoin or the like can be used.
  • the oxidizing agent is a metal oxide
  • the amount of the oxidizing agent used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1b). It is equal to or more than 200 equivalents.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, dichloromethane, dichloroethane, chloroform, Examples include a halogen-based solvent such as carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (1b). is there.
  • the temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 0 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
  • a post-treatment of the reaction metals that are not dissolved can be removed by filtration. Furthermore, a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane.
  • ether solvents such as t-butyl ether
  • halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride
  • hydrocarbon solvents such as hexane, heptane,
  • these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
  • the number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. In this reaction, a liquid separation operation is not essential.
  • reaction mixture containing the compound represented by the formula (1a) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • reaction mixture containing the compound represented by the formula (1a) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • the oxidizing agent is a benzoquinone
  • the amount of the oxidizing agent used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1b). It is equal to or more than 20 equivalents.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, dichloromethane, dichloroethane, chloroform, Examples include a halogen-based solvent such as carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (1b). is there.
  • the temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 0 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
  • liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane.
  • ether solvents such as t-butyl ether
  • halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride
  • hydrocarbon solvents such as hexane, heptane,
  • these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
  • the number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. In this reaction, a liquid separation operation is not essential.
  • reaction mixture containing the compound represented by the formula (1a) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • reaction mixture containing the compound represented by the formula (1a) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • the oxidizing agent is a combination of a radical initiator and a halogenating agent.
  • the amounts of the radical initiator and the halogenating agent used in this reaction are 0.01 equivalent or more and 1.0 equivalent or more with respect to the compound represented by the formula (1b), respectively, the desired reaction proceeds. There is no particular limitation as long as it does.
  • the amount of the radical initiator is from 0.01 to 1 equivalent, and the amount of the halogenating agent is from 1 to 3 equivalents.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is preferably a halogenated benzene solvent such as chlorobenzene or dichlorobenzene, or an ester solvent such as ethyl acetate, isopropyl acetate or butyl acetate.
  • Solvents include halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (1b). is there.
  • the temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 20 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
  • liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved
  • an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved
  • thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate or butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, and chloroform, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, may be added. It is possible. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
  • reaction mixture containing the compound represented by the formula (1a) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • reaction mixture containing the compound represented by the formula (1a) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • R5b represents a halogen atom
  • HalR represents a halogenating agent
  • R1, R2, R3, R4, X and Y are as defined above.
  • Production method F is a method for obtaining a compound represented by the formula (1a-b) in which R5b represents a halogen atom among the compounds represented by the formula (1a). And a halogenating agent (HalR) in a solvent.
  • R5b represents a halogen atom among the compounds represented by the formula (1a).
  • a halogenating agent (HalR) in a solvent.
  • halogenating agent used in this reaction examples include selectrofluor (N-fluoro-N′-chloromethyl-triethylenediamine bis (tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodo Succinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine and the like.
  • the amount of the halogenating agent used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1a-a). Preferably, it is 1 equivalent or more and 10 equivalents or less. However, the amount of the halogenating agent containing hydantoin is not particularly limited as long as the desired reaction proceeds as long as the amount is 0.5 equivalent or more, and preferably 1 equivalent to 5 equivalents.
  • an acid such as an inorganic acid such as hydrochloric acid or sulfuric acid or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid, or trifluoromethanesulfonic acid is added.
  • an acid such as an inorganic acid such as hydrochloric acid or sulfuric acid or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid, or trifluoromethanesulfonic acid is added.
  • an inorganic acid such as hydrochloric acid or sulfuric acid
  • an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid, or trifluoromethanesulfonic acid is added.
  • the desired reaction can be achieved. There is no particular limitation as long as it proceeds, but it is preferably 0.1 equivalent or more and 3 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid, and diethyl ether , Diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane and other ether solvents, methanol, ethanol, isopropanol and other alcohol solvents, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene and other benzene solvents Solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc., nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 times or more and 200 times or more the compound represented by the formula (1a-a). It is as follows.
  • the temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 0 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
  • liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved
  • an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved
  • thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
  • reaction mixture containing the compound represented by the formula (1a-b) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • reaction mixture containing the compound represented by the formula (1a-b) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (1a-b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • J represents an oxygen atom or a sulfur atom
  • R5c represents a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group optionally substituted
  • C2-C6 alkenyl group optionally substituted with substituent A C2-C6 haloalkenyl group, C3 optionally substituted with substituent A
  • Q represents a hydrogen atom or a metal.
  • R1, R2, R3, R4, R5b, X and Y are as defined above.
  • J represents an oxygen atom or a sulfur atom
  • R5c is a group represented by C1 to C6 which may be appropriately substituted with a substituent A.
  • R5b is a chlorine atom, a bromine atom, or an iodine atom.
  • RR5c-JQ used in this reaction is commercially available or can be produced by a known method.
  • Preferred Q is a hydrogen atom or an alkali metal such as sodium or potassium.
  • the amount of R5c-JQ used in this reaction is not particularly limited as long as the amount of the compound represented by the formula (1a-b) is 1 equivalent or more, as long as the desired reaction proceeds. .
  • Q is a hydrogen atom, it can be used also as a solvent.
  • the transition metals used in this reaction may have a ligand and include palladium acetate, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, tris (dibenzylideneacetone) dipalladium, tetrakis ( And palladiums such as triphenylphosphine) palladium and bis (triphenylphosphine) palladium dichloride.
  • the amount of the transition metals used in this reaction is 0.001 equivalent or more and 1 equivalent or less based on the compound represented by the formula (1a-b), but is not particularly limited as long as the desired reaction proceeds. None.
  • triphenylphosphine 1,1′-bis (diphenylphosphino) ferrocene, 2-dicyclohexylphosphino-2′4′6′-triisopropylbiphenyl, 2-di-t
  • a phosphine ligand such as -butylphosphino-2'4'6'-triisopropylbiphenyl can be added.
  • the amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less based on the compound represented by the formula (1a-b), but is not particularly limited as long as the desired reaction proceeds. It will not be done.
  • the base used in this reaction is an inorganic base such as sodium carbonate, potassium carbonate or cesium carbonate, or an organic base such as triethylamine, tributylamine or diisopropylethylamine.
  • the amount of the base used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1a-b), but is preferably 1 to 50 equivalents.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but R5c-JH (wherein R5c is as defined above, and J is an oxygen atom. ), Ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene. Is mentioned. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 times or more and 200 times or more the compound represented by the formula (1a-b). It is as follows.
  • the temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 30 ° C or more and 200 ° C or less or the boiling point of the solvent or less.
  • liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane.
  • ether solvents such as t-butyl ether
  • halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride
  • hydrocarbon solvents such as hexane, heptane,
  • these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
  • the number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. It is also possible, but not essential, to remove insolubles by performing a filtration operation.
  • reaction mixture containing the compound represented by the formula (1a-c) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • reaction mixture containing the compound represented by the formula (1a-c) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by formula (1a-c) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • R5d represents a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a substituent A Represents an optionally substituted C2-C6 alkenyl group or a C2-C6 haloalkenyl group
  • R5d-B represents an organic boronic acid
  • R1, R2, R3, R4, R5b, X and Y are as defined above. Is synonymous with
  • R5d is a C1-C6 alkyl group, a C1-C6 haloalkyl group or a substituent A, which may be appropriately substituted with a substituent A.
  • a process comprising the step of reacting a compound of formula (1a-b) with an organoboronic acid (R5d-B) in the presence of a transition metal and a base by Suzuki-Miyaura coupling. Is the way.
  • R5b is a chlorine atom, a bromine atom, or an iodine atom.
  • RR5d-B used in this reaction represents an organic boronic acid such as an organic boronic acid or an organic boronic ester, and can be obtained as a commercial product or can be produced by a known method.
  • the amount of R5d-B used in this reaction is not particularly limited as long as the desired reaction proceeds as long as the amount of the compound represented by the formula (1a-b) is 1 equivalent or more. Preferably, it is 1 equivalent or more and 10 equivalents or less.
  • the transition metals used in this reaction are palladium, nickel, ruthenium and the like, and may have a ligand.
  • Palladium is mentioned.
  • the amount of the transition metals used in this reaction is 0.001 equivalent or more and 1 equivalent or less based on the compound represented by the formula (1a-b), but is not particularly limited as long as the desired reaction proceeds. None.
  • Phosphine ligands such as triphenylphosphine and tricyclohexylphosphine can be added to make this reaction proceed efficiently.
  • the amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less based on the compound represented by the formula (1a-b), but is not particularly limited as long as the desired reaction proceeds. It will not be done.
  • the base used in the present reaction is an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate or tripotassium phosphate, or a metal alkoxide such as sodium methoxide, sodium ethoxide or potassium @ t-butoxide.
  • the amount of the base used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1a-b), but is preferably 1 to 50 equivalents.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but an aqueous solvent, an ether such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc.
  • Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 times or more and 200 times or more the compound represented by the formula (1a-b). It is as follows.
  • the temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 30 ° C or more and 200 ° C or less or the boiling point of the solvent or less.
  • liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane.
  • ether solvents such as t-butyl ether
  • halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride
  • hydrocarbon solvents such as hexane, heptane,
  • these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
  • the number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. It is also possible, but not essential, to remove insolubles by performing a filtration operation.
  • reaction mixture containing the compound represented by the formula (1a-d) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • reaction mixture containing the compound represented by the formula (1a-d) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (1a-d) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • R5e represents a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with the substituent A, and R1, R2, R3, R4, R5b, X and Y are as defined above. It is.
  • R5e is a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with a substituent A.
  • e) a method for synthesizing a compound represented by (e), comprising obtaining the compound represented by (1a-b) and a terminal alkyne compound by Sonogashira coupling in the presence of a transition metal and a base. It is a manufacturing method.
  • R5b is a chlorine atom, a bromine atom, or an iodine atom.
  • the terminal alkyne compound used in this reaction can be obtained as a commercial product or can be produced by a known method. Further, trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to introduce a trimethylsilylethynyl group into the compound represented by the formula (1a-b) and then perform desilylation. Regarding desilylation, see Journal of the American Chemical Society, vol. 131, No. 2, pp. 634-643 (2009), Journal of the American Chemical Society. And Journal of Organometallic Chemistry, 696, 25, pp. 4039-4045 (2011). And the like.
  • the amount of the terminal alkyne compound used in this reaction is not particularly limited as long as the intended reaction proceeds, provided that the amount of the terminal alkyne compound is at least 1 equivalent to the compound represented by the formula (1a-b). Preferably, it is 1 equivalent or more and 10 equivalents or less.
  • the transition metals used in this reaction may have a ligand and include palladium acetate, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, tris (dibenzylideneacetone) dipalladium, tetrakis ( And palladiums such as triphenylphosphine) palladium and bis (triphenylphosphine) palladium dichloride.
  • coppers such as copper chloride, copper bromide, and copper iodide are used at the same time.
  • the amount of the transition metal used in this reaction may be at least 0.001 equivalent of the palladium or the like and the copper to the compound represented by the formula (1a-b), respectively. There is no particular limitation as long as it is done. Preferred amounts are 0.001 equivalent to 1 equivalent in both cases.
  • Examples of the base used in the present reaction include organic amines such as triethylamine, tributylamine, isopropylamine, diethylamine, diisopropylamine and diisopropylethylamine, and inorganic bases such as sodium carbonate, potassium carbonate and cesium carbonate.
  • organic amines such as triethylamine, tributylamine, isopropylamine, diethylamine, diisopropylamine and diisopropylethylamine
  • inorganic bases such as sodium carbonate, potassium carbonate and cesium carbonate.
  • the amount of the base used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1a-b), but is preferably 1 to 50 equivalents.
  • an organic base in a liquid state can be used as a solvent.
  • a phosphine ligand such as tri-t-butylphosphine or 2-dicyclohexylphosphino-2′4′6′-triisopropylbiphenyl can be added for efficient progress of the reaction, but is not essential. .
  • the amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less based on the compound represented by the formula (1a-b), but is not particularly limited as long as the desired reaction proceeds. It will not be done.
  • ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane;
  • Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N, N-dimethylformamide
  • Solvents such as amide solvents such as N, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon t
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 times or more and 200 times or more the compound represented by the formula (1a-b). It is as follows.
  • the temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 0 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
  • liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane.
  • ether solvents such as t-butyl ether
  • halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride
  • hydrocarbon solvents such as hexane, heptane,
  • these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
  • the number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. It is also possible, but not essential, to remove insolubles by performing a filtration operation.
  • reaction mixture containing the compound represented by the formula (1a-e) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • reaction mixture containing the compound represented by the formula (1a-e) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (1a-e) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • Rya represents a C1 to C6 alkoxy group
  • Ya represents a thiophen-2-yl group or a thiophen-3-yl group
  • R1, R2, R3, R4, R5, X and the dashed line represent Is synonymous with
  • Production method J is a method for synthesizing a compound represented by the formula (1-b) having a hydroxyl group among the compounds represented by the formula (1), wherein Rya is a C1-C6 alkoxy group. This is a production method including obtaining the compound represented by 1-a) by reacting the compound with an acid.
  • Examples of the acid used in the reaction include boron halides such as boron trichloride and boron tribromide.
  • the amount of the acid used in this reaction may be at least 1 equivalent to the compound represented by the formula (1-a), and is not particularly limited as long as the desired reaction proceeds, but is preferably Is 1 equivalent or more and 10 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, and nitrile solvents such as acetonitrile.
  • Halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 times or more and 200 times or more the weight of the compound represented by the formula (1-a). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually ⁇ 80 ° C. or more and 100 ° C. or less or the boiling point of the solvent or less.
  • liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
  • reaction mixture containing the compound represented by the formula (1-b) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • the solvent can be distilled off under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (1-b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • Ryb is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent A C2-C6 alkenyl group optionally substituted with C, a C2-C6 haloalkenyl group, a C3-C6 alkynyl group optionally substituted with a substituent C, a C3-C6 haloalkynyl group, a substituent An aryl group optionally substituted with 0 to 5 substituents D, a heteroaryl group optionally substituted with 0 to 2 substituents D, an aralkyl group optionally substituted with 0 to 5 substituents D, or Rx1C ( OO)-, and Lv, R1, R2, R3, R4, R5, Rx1, X, Ya and the broken line have the same meanings as above.
  • Ryb is optionally substituted with a C1 to C6 alkyl group, a C1 to C6 haloalkyl group or a substituent C, which may be appropriately substituted with a substituent C.
  • RRyb-Lv used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • Ryb-Lv used in this reaction may be at least 1 equivalent to the compound represented by the formula (1-b), and is not particularly limited as long as the desired reaction proceeds, but is preferably used. Is 1 equivalent or more and 10 equivalents or less.
  • Examples of the base used in this reaction include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and sodium hydride, and organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine and lutidine.
  • inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and sodium hydride
  • organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine and lutidine.
  • organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine and lutidine.
  • the base used in this reaction may be at least 1 equivalent to the compound represented by the formula (1-b), and is not particularly limited as long as the desired reaction proceeds. It is 1 equivalent or more and 10 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; Alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; Amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane,
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually at least 3 times by weight to 200 times by weight the compound represented by the formula (1-b). It is as follows.
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually -20 ° C or more and 150 ° C or less or the boiling point of the solvent or less.
  • liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved
  • an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved
  • thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
  • reaction mixture containing the compound represented by the formula (1-c) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • the solvent can be distilled off under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (1-c) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • Rxa in the compound represented by the formula (1-d) and the formula (1-e) Rya in the compound represented by the formula (1-d), and the compound represented by the formula (1-e)
  • the hydroxyl group in the formula (1) is substituted at any position corresponding to R2, R3 or R4 in the compound represented by the formula (1).
  • the production method L is a method for synthesizing a compound represented by the formula (1-e) having a hydroxyl group among the compounds represented by the formula (1), wherein the compound represented by the formula (1-d) It is a production method including obtaining by reacting with an acid.
  • production method L can be carried out according to production method J. it can.
  • Lv, R1, R5, Rxa, Ryb, X, Y, na and the broken line have the same meaning as described above.
  • Rxa in the compound represented by the formula (1-e) and the formula (1-f) the hydroxyl group in the compound represented by the formula (1-e), and the compound represented by the formula (1-f) Ryb-O- in the formula is substituted at any position corresponding to R2, R3 or R4 in the compound represented by the formula (1).
  • na 2
  • Rxa of 2 represents an independent substituent.
  • the production method M is a method for synthesizing the compound represented by the formula (1-f) among the compounds represented by the formula (1), wherein the compound represented by the formula (1-e) and Ryb-Lv And a reaction in the presence of a base in a solvent.
  • the production method M can be carried out according to the production method K. it can.
  • Ryc represents a halogen atom
  • Yb represents a thiophen-2-yl group or a thiophen-3-yl group
  • Ryd represents a C1-C6 alkyl group optionally substituted with a substituent C
  • Ryd-B represents an organic boronic acid
  • R1, R2, R3, R4, R5, X and the broken line have the same meanings as described above.
  • Ryd is appropriately substituted with a C1 to C6 alkyl group, a C1 to C6 haloalkyl group or a substituent C, which may be appropriately substituted with a substituent C.
  • preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
  • Ryd-B used in this reaction represents an organic boronic acid such as an organic boronic acid or an organic boronic ester, and can be obtained as a commercial product or can be produced by a known method.
  • the production method H By using the compound represented by the formula (1a-b) and R5d-B in the production method H in place of the compound represented by the formula (1-g) and Ryd-B, respectively, the production method H
  • the manufacturing method N can be performed according to
  • Rxb is a hydrogen atom, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, or a C3 optionally substituted with a substituent C.
  • C8-C8 cycloalkyl group C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2 A C1 to C6 haloalkynyl group optionally substituted with a substituent C, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group optionally substituted with a substituent C, A C2-C6 alkenyloxy group optionally substituted with a substituent C, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy optionally substituted with a substituent C , A C3-C6 haloalkynyloxy group, an aryloxy group optionally substituted with 0 to 5 substituents D, a heteroaryloxy group optionally substituted with 0 to 2 substituents D, and an appropriate
  • Rxb in the compound represented by the formula (1-i) and the formula (1-j), Ryc in the compound represented by the formula (1-i), and the compound represented by the formula (1-j) Ryd in the formula (1) is substituted at any position corresponding to R2, R3 or R4 in the compound represented by the formula (1).
  • Rxb of 2 represents an independent substituent.
  • Production method O is a method for synthesizing the compound represented by the formula (1-j) among the compounds represented by the formula (1), wherein the compound represented by the formula (1-i) and the organic boronic acid (Ryd-B) to obtain a Suzuki-Miyaura coupling.
  • preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
  • the production method H By using the compound represented by the formula (1a-b) and R5d-B in the production method H in place of the compound represented by the formula (1-i) and Ryd-B, respectively, the production method H
  • the manufacturing method O can be performed according to
  • Rye represents a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with a substituent C
  • Ryc, R1, R2, R3, R4, R5, X, Yb and a broken line The parts are as defined above.
  • Rye is a C2-C6 alkynyl group optionally substituted with a substituent C or a C2-C6 haloalkynyl group.
  • preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
  • production method P can be carried out according to production method I. .
  • Rxb, Ryc, Rye, R1, R5, X, Y, na, and the broken line have the same meanings as described above.
  • the compound represented by the formula (1-1) Rye in the formula (1) is substituted at any position corresponding to R2, R3 or R4 in the compound represented by the formula (1).
  • Rxb of 2 represents an independent substituent.
  • the production method P is a method for synthesizing a compound represented by the formula (1-1) among the compounds represented by the formula (1), wherein the compound represented by the formula (1-i) and a terminal alkyne compound And Sonogashira coupling.
  • preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
  • the production method Q can be carried out according to the production method I. .
  • La represents S
  • Lb represents SO or SO 2
  • Ox ′ represents an oxidizing agent
  • Production method R is in the compounds of formula (1), manufacture of R1, R2, R3, R4, R5, and Lb contained in R6 is represented by the formula (Lb) is SO or SO 2
  • Examples of the oxidizing agent used in the present reaction include peroxides such as aqueous hydrogen peroxide and meta-chloroperbenzoic acid. Also, transition metals such as sodium tungstate can be added.
  • the amount of oxidizing agent used in this reaction, to the compound represented by the formula (La) in the manufacture of SO, is usually, 1.0 1.2 equivalents or less equivalent or more, producing SO 2 In doing so, it is usually 2 equivalents or more and 10 equivalents or less. In addition, when a transition metal is added, it is usually 0.001 equivalent or more and 1 equivalent or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is not limited to an aqueous solvent, an acidic solvent such as acetic acid, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and the like.
  • an acidic solvent such as acetic acid, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and the like.
  • examples thereof include benzene solvents, nitrile solvents such as acetonitrile, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (La). is there.
  • the temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually -10 ° C or more and 120 ° C or less or the boiling point of the solvent or less.
  • liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved
  • an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved
  • thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
  • reaction mixture containing the compound represented by the formula (Lb) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • reaction mixture containing the compound represented by the formula (Lb) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by formula (Lb) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • R2, R3, R4, R5, R8, X and Y are as defined above.
  • the production method S is a method for producing a production intermediate represented by the formula (3), in which a compound represented by the formula (5) and a compound represented by the formula (6) are dissolved in a solvent in the presence of a base. And a reaction method comprising reacting
  • the compound represented by the formula (6) used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • the amount of the compound represented by the formula (6) used in this reaction is not particularly limited as long as the target reaction proceeds as long as the amount of the compound represented by the formula (5) is 1 equivalent or more. But not more than 1 equivalent and not more than 3 equivalents.
  • the base used in the present reaction is an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate or tripotassium phosphate, or a metal alkoxide such as sodium methoxide, sodium ethoxide or potassium @ t-butoxide.
  • the base used in this reaction can be carried out in a catalytic amount, and is not particularly limited as long as the desired reaction proceeds, but is preferably a compound represented by the formula (5). On the other hand, it is 0.01 to 3 equivalents.
  • Solvents used in this reaction include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; Ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide and N, N-dimethylacetamide; 1,3-dimethyl Urea solvents such as -2-imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride; sulfur solvents such as dimethyl s
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (5). is there.
  • the temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually -50 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
  • liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
  • reaction mixture containing the compound represented by the formula (3) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • reaction mixture containing the compound represented by the formula (3) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (3) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • R8a represents a C1 to C6 alkyl group
  • R2, R3, R4, R5, X and Y are as defined above.
  • the production method T is a method for producing a production intermediate represented by the formula (3b) among the compounds represented by the formula (3), wherein the compound represented by the formula (3a) is prepared under an acidic condition or a base condition.
  • This is a production method comprising reacting in a solvent under ionic conditions.
  • Examples of the acid used in the present reaction include inorganic acids such as hydrochloric acid, hydrobromic acid and phosphoric acid, and organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid and trifluoroacetic acid. There is no particular limitation as long as the desired reaction proceeds.
  • the amount of the acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the desired reaction proceeds, but is preferably 0.1 to 0.1 with respect to the compound represented by the formula (3a). It is at least 01 equivalent. Further, a liquid acid can be used as a solvent.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds.
  • aqueous solvents acidic solvents such as acetic acid and methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t- Ether solvents such as butyl ether, dimethoxyethane, tetrahydrofuran and dioxane; alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ethyl acetate, isopropyl acetate and acetic acid Ester solvents such as butyl, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (3a). is there.
  • the temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 0 ° C or higher and 180 ° C or lower or the boiling point of the solvent or lower.
  • the base used in this reaction is exemplified by inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide, but is not particularly limited as long as the desired reaction proceeds.
  • the base used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (3a), but is preferably at least 1 equivalent. It is 30 equivalents or less.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but an aqueous solvent, ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane Solvents, alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; and nitriles such as acetonitrile Solvent, amide solvent such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvent such as 1,3-dimethyl-2-imidazolidinone, dich
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (3a). is there.
  • the temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually -20 ° C or more and 180 ° C or less or the boiling point of the solvent or less.
  • the post-treatment of the reaction can be performed by a common method for the reaction under acidic conditions and the reaction under basic conditions. Separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
  • reaction mixture containing the compound represented by the formula (3b) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • the solvent can be distilled off under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by formula (3b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • the compound represented by the formula (3b) has the formula (3b ′) (In the formula, R2, R3, R4, R5, X and Y are as defined above.)
  • the isomer represented by is also included.
  • the compound represented by the formula (3b ') can be handled in the same manner as the compound represented by the formula (3b), and the production method A can be applied. Further, the compound represented by the formula (3b ') contains an asymmetric carbon, and the isomers may be used alone or in a mixture at an arbitrary ratio. Furthermore, a mixture of the compound represented by the formula (3b) and the compound represented by the formula (3b ′) may be used, and the mixing ratio of the isomers may be singly or a mixture having an arbitrary ratio.
  • R1, R2, R3, R4, R5b, X and Y are as defined above.
  • Production method U is a method for synthesizing a compound represented by the formula (1a-f) having a trifluoromethyl group among the compounds represented by the formula (1a), and is represented by the formula (1a-b).
  • the method comprises reacting a compound with methyl difluoro (fluorosulfonyl) acetate in the presence of transition metals.
  • R5b is a chlorine atom, a bromine atom, or an iodine atom.
  • Methyl difluoro (fluorosulfonyl) acetate used in this reaction can be obtained as a commercial product or can be produced by a known method.
  • the amount of methyl difluoro (fluorosulfonyl) acetate used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as the amount of the compound represented by the formula (1a-b) is 1 equivalent or more. However, it is preferably 1 equivalent or more and 50 equivalents or less.
  • the transition metals used in this reaction are coppers and the like.
  • copper bromide, copper iodide and the like are used.
  • the amount of the transition metals used in this reaction may be at least 1 equivalent to the compound represented by the formula (1a-b), and is not particularly limited as long as the desired reaction proceeds. However, it is preferably 1 equivalent or more and 50 equivalents or less.
  • an additive such as ethyldiisopropylamine or hexamethylphosphoric triamide can be added, but is not essential.
  • the amount of the additive used in this reaction is not more than 50 equivalents to the compound represented by the formula (1a-b), and is not particularly limited as long as the desired reaction proceeds.
  • the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, Sulfur-based solvents such as dimethyl sulfoxide and sulfolane. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
  • the amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 times or more and 200 times or more the compound represented by the formula (1a-b). It is as follows.
  • the temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 0 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
  • liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture.
  • an aqueous solution an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved, an alkaline aqueous solution in which ammonia, potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. are dissolved,
  • An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium thiosulfate or sodium sulfite is dissolved can be arbitrarily used.
  • a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
  • reaction mixture containing the compound represented by the formula (1a-f) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
  • a desiccant such as sodium sulfate or magnesium sulfate
  • reaction mixture containing the compound represented by the formula (1a-f) obtained above can be evaporated under reduced pressure as long as the compound is not decomposed.
  • reaction mixture containing the compound represented by the formula (1a-f) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
  • the compound represented by the formula (1) can be produced by arbitrarily combining the production methods A to U described above.
  • the compound represented by the formula (1) can be produced by arbitrarily combining a known method with Production Methods A to U.
  • the compound of the present invention can control harmful organisms to plants, it can be used as a pesticide, particularly a pesticide for agricultural and horticultural use.
  • a pesticide particularly a pesticide for agricultural and horticultural use.
  • Specific examples include fungicides, insecticides, herbicides, plant growth regulators, and the like.
  • it is a bactericide.
  • the compound of the present invention can be used as an agricultural and horticultural fungicide in fields, paddy fields, tea fields, orchards, pastures, lawns, forests, gardens, street trees, and the like for controlling plant diseases.
  • the plant diseases referred to in the present invention are crops, flowers, flowers, trees, trees, and other plants. , Partial pathological symptoms such as cigars, wilt, root rot, nodules, nodules and the like. That is, the plant becomes ill.
  • Pathogens causing plant diseases mainly include fungi, bacteria, spiroplasmas, phytoplasmas, viruses, viroids, parasitic higher plants, nematodes and the like.
  • the compound of the present invention is effective on fungi, but is not limited thereto.
  • Fungi pathogens which cause fungal diseases include fungus fungi, oomycetes, zygomycetes, ascomycetes, basidiomycetes and incomplete fungi.
  • fungus fungi root-knot fungus, powdery mildew fungus, sugar beet wilt fungus, oomycete, downy mildew, Pythium genus, Aphanomyces genus, zygomycetes Rhizopus genus, ascomycetes Fungi include peach leaf blight, corn sesame leaf blight, rice blast, powdery mildew, anthracnose, red mold, bacillus seedling, sclerotium, basidiomycetes, rust, smut, and purple print Fungi, rice blast, sheath blight, and imperfect fungi include gray mold, Alternaria, Fusarium, Penicillium, Rhizoctonia, and white silk.
  • the compound of the present invention is effective against various plant diseases.
  • specific examples of the disease name and the pathogen name will be shown.
  • Rice blast (Magnaporthe grisea), sheath blight (Thanatephorus cucumeris), brown rot (Ceratobasidium setariae), brown sclerotium (Waitea circinata), brown spot rot spelling bacterium (Therca erucorus phus) Sclerotium hydrophilum, red rot (Wairea circinata), black rot (Entyloma dactylidis), pneumococcal disease (Magnaporthe salvinii leaf blight, Ceratobosa sigma rot) Blight disease (Sphaerulina oryzina) , Frog seedling disease (Gibberella fujikuroi), seedling blight (Pythium spp., Fusarium spp., Trichoderma spp., Rhizopus spp., Rhizonia spore, Rhizoctonia spore, Rhizoptonia solipani, M
  • Tritici Tritici
  • rust Puccinia striiformis, Puccinia graminis, Puccinia reconitia, Puccinia reconia, Puccinia reconia, Puccinia reconitia, Puccinia reconitia) Pyrenophora teres
  • Fusarium zeae Fusarium culmorum, Fusarium avenaceum, Monographella nivalis, Snow rot (Typhula incarina, Typhula inicarina, Typhula iniganeis raisulai sushi) nuda), fishy smell smut (Tilletia caries, Tilletia controversa), Memonbyo (Pseudocercosporella herpotrichoides), stock rot (Ceratobasidium gramineum), scald (Rhynchosporium secalis), leaf blight (Septoria trit
  • Syringae Fusarium avenaceum, Penicillium spp, Pythium spp., Rhizoctonia spp., Pustinia sorghum scab (Puccinia sorghum), rust (Puccinia sorghum), and rust (Puccinia sorghum), corn leafy mildew (Gibberella zeae, etc.), seedling blight (Fusarium avenaceum, Penicillium spp, Pythium spp., Rhizoctonia sp.
  • Ustilago maydis, anthrax (Colletotrichum graminicola), northern leaf spot (Cochliobolus carbumum), brown streak (Acidovorax avene ssp. ), Fusarium wilt disease (Erwinia stewartii); Grape downy mildew (Plasmopara viticola), rust (Physopella ampelopsidis), powdery mildew (Uncinula necrotor, Elus erin aelin erin aelin erin aelin ell ella melin elsa) , Colletotrichum acutatum, black rot (Guignardia bidwellii), vine disease (Phomopsis viticola), soybean spot disease (Zygophiala jamaicensis), gray mold disease (Butterydiae blight disease) Helicobasidium mompa), white crest Disease (Rosellinia necatri
  • Erwinia sp. Apical carcinoma (Agrobacterium tumefaciens), rust-colored blight (Erwinia chrysanthemi pv. Chrysanthemi), and rot bacterial disease (Pseudomonas syringa spores).
  • s ringae bacterial wilt disease
  • peach scab Cerach scab
  • homopsis rot Pieris sp.
  • plague Phytophthora spp.
  • anthrax Coldletotrophithosporium
  • deformans perforated bacterial disease (Xhanthomonas campestris pv.
  • syringae greening disease
  • Liberactor asiaticus greening disease
  • apical carcinoma Agrobacterium tumefaciens
  • Botrytis cinerea such as tomato, cucumber, beans, strawberries, potatoes, cabbage, eggplant, lettuce
  • sclerotinia sclerotium such as tomato, cucumber, beans, strawberry, potato, rapeseed, cabbage, eggplant, lettuce
  • Tomato cucumber, legumes, radish, watermelon, eggplant, rapeseed, bell pepper, spinach, sugar beet, and various other types of seedling wilt (Rhizoctonia spp., Pythium spp., Fusarium spp., Phylophthroprosa sp., Etc.) Rustonia solanacearum of Solanaceae; downy mildew of cucumber (Pseudoperonospora cubens); s), powdery mildew (Sphaerotheca fuliginea),
  • ytoplasma asteris yellow dwarf (Tobacco leaf curl subgroup III geminivirus); Brown spot bacterial disease (Pseudomonas cichorii), stem nematode bacterial disease (Pseudomonas corrugata), stem rot bacterial disease (Erwinia chrysanthemi), soft rot (Erwinia carotovora spores, spores of spores, spores, spores, spores, spores and germs).
  • Black rot Alternaria brassicae
  • black rot Xhanthomonas campestris pv.
  • Campestris black rot (Pseudomonas syringae pv. Eravia kuroa eroa var. Etc.), white spot disease (Cercosporella brassicae), root rot disease (Pharma lingam), clubroot disease (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), black rot disease (Xhancamposamposa. campestris), black spot bacterial disease (Pseudomonas syringae pv. maculicola), soft rot (Erwinia carotovora subsp.
  • soybean purpura (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phasoolz, rhizopha spores and lysophia rotoh rotoh rotonia sarcopodium) e), downy mildew (Peronospora manshurica), rust (Phakopsora pachyrhizi), anthrax (Colletotrichum truncatum, etc.), leaf blight (Xanthomonas camps pesgos pest.
  • Anthrax Coldletotrichum lindemutianum
  • bacterial wilt Ralstonia solanacearum
  • scab Pseudomonas syringae pv. Phaseolicola
  • brown spot bacterial disease Pseudomonas visamrais virions virion virion virion virion virion virion virion virion sv. v.
  • phaseoli Phaseoli
  • Peanut black spot Mycosphaerella berkeleyi
  • brown spot Mycosphaerella arachidis
  • wilt Ralstonia solanacearum
  • pea powdery mildew Erysiphe pisi
  • downy mildew Peros pero spelling, Peros pero spelling, downy mildew
  • syringae pv. pisi vine rot
  • Carotovora viscous rot (Crostridium spicia sibim. Sweetpotato wilt (Streptomyces ipomoea); Sugar beet brown spot (Cercospora beticola), downy mildew (Peronospora schachyti), black root rot (Aphanomychoes schoensis, Aphanomychoes schoensis). Agrobacterium tumefaciens, scab (Streptomyces scabies), spot bacterial disease (Pseudomonas syringae pv.
  • Apata Bacterial leaf blight of carrots (Alternaria dauci), club scab (Rhizobacter dauci), apical carcinoma (Agrobacterium tumefaciens), Streptomyces scab (Streptomyces spop. Powdery mildew of strawberry (Sphaerotheca aphanis var.
  • Aphanis plague (Phytophthora nicotiana, etc.), anthrax (Glomerella singulata, etc.), fruit rot (Pythium ultimum), bacterial rot (Stium rustum), Xanthus wilt disease, Xanthus wilt disease campestris), Bacterial blight (Pseudomonas marginalis pv. Marginalis); tea blast (Exobasidium reticulatum), white scab (Elsinoe leucospila), anthrax (Colletotrichus stomach disease) syringae pv. theae, scabs (Xhanthomonas campestris pv.
  • Fusarium sickness (Sphaerotheca pannosa, etc.), plague (Phytophthora megasperma), downy mildew (Peronospora sparsa), root carcinoma (Agrobacterium tumefaciens), chrysanthemum spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore sb. ), Plague (Phytophthora actorum), spot bacterial disease (Pseudomonas ichorii), soft rot (Erwinia carotovora subsp
  • ifolia turf brown patch disease (Rhizoctonia solani), dollar spot disease (Sclerotinia homoeocarpa), carburaria leaf blight (Curvularia sp.), rust (Puccinia zoysia sp.
  • the compound of the present invention may be used alone, but preferably is mixed with a solid carrier, liquid carrier, gas carrier, surfactant, fixing agent, dispersant, stabilizer, etc. It can be used as a composition such as water dispersible granules, aqueous solvents, aqueous granule solvents, granules, emulsions, liquids, microemulsions, aqueous suspensions, aqueous emulsions, and suspoemulsions.
  • the composition is not limited as long as the effect is exhibited.
  • composition containing the compound of the present invention a pesticide for agricultural and horticultural use, a fungicide for agricultural and horticultural use, and the like
  • a method for applying the composition containing the compound of the present invention include a method in which the composition is brought into contact with a plant or a seed, and a method in which the composition is contained in a cultivated soil and brought into contact with a root or a rhizome of a plant.
  • foliage spraying treatment injection treatment, seedling box treatment, cell tray treatment, spraying treatment on plant seeds, spray treatment on plant seeds, immersion treatment on plant seeds, immersion treatment on plant seeds, on plant seeds of the composition Dressing, spraying on the soil surface, soil mixing after spraying on the soil surface, injection into the soil, soil mixing after injection in the soil, soil irrigation, after soil irrigation Soil mixing and the like.
  • any method of application as used by those skilled in the art will work well.
  • Plant ”as used in the present invention refers to a plant that performs photosynthesis and lives without exercise. Specific examples include rice, wheat, barley, corn, coffee, banana, grape, apple, pear, peach, cherry, oyster, citrus, soybean, bean, cotton, strawberry, potato, cabbage, lettuce, tomato, cucumber, eggplant, Watermelon, sugar beet, spinach, snow pea, pumpkin, sugar cane, tobacco, bell pepper, sweet potato, taro, konjac, cotton, sunflower, rose, tulip, chrysanthemum, turf, etc. and their F1 varieties and the like can be mentioned. It also includes genetically modified crops that are produced by manipulating genes and the like and are not originally present in the natural world.
  • plants in the present invention is a general term for all the parts constituting the above-mentioned plant individual, and includes, for example, stems, leaves, roots, seeds, flowers, fruits and the like.
  • ⁇ The“ seed ”in the present invention refers to a seed that stores nutrients for germinating young plants and is used for agricultural reproduction.
  • Specific examples include corn, soybean, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, snow peas, pumpkin, sugar cane, tobacco, peppers, oilseed rape and other seeds, and their F1 varieties and the like.
  • Examples include seeds, seed potatoes such as taro, potato, sweet potato, and konjac, edible lilies, bulbs such as tulips, seed balls such as raccoon, and seeds and tubers of genetically modified crops.
  • the application rate and application concentration of the composition containing the compound of the present invention vary depending on the target crop, the target disease, the degree of occurrence of the disease, the dosage form of the compound, the application method, and various environmental conditions.
  • the amount of the active ingredient is suitably from 0.1 to 10,000 g per hectare, preferably from 10 to 1,000 g per hectare. In the case of seed treatment, the amount used is 0.0001 to 1000 g, preferably 0.001 to 100 g, per kg of seed as an active ingredient.
  • the composition containing the compound of the present invention is used as a foliage spraying treatment on a plant individual, a spraying treatment on a soil surface, an injection treatment into soil or a soil irrigation treatment, the composition is diluted with an appropriate carrier at an appropriate concentration.
  • the processing may be performed.
  • the composition containing the compound of the present invention When the composition containing the compound of the present invention is brought into contact with a plant seed, it may be diluted to an appropriate concentration and then immersed, dressed, sprayed or smeared on the plant seed before use.
  • the amount of the composition used for immersion, dressing, spraying or smearing is usually about 0.05 to 50%, preferably 0.1 to 30% of the weight of the dried plant seeds as an active ingredient. Is appropriate, but may be appropriately set depending on the form of the composition and the type of plant seed to be treated, and is not limited to these ranges.
  • the compound of the present invention may contain, if necessary, other pesticides, for example, pesticides such as fungicides, insecticides (including acaricides and nematicides), herbicides, microbial materials, and plant growth regulators, and nucleic acids. It can be used as a mixture with a disease control agent (WO 2014/062775), a soil conditioner or a fertilizer as an active ingredient.
  • pesticides such as fungicides, insecticides (including acaricides and nematicides), herbicides, microbial materials, and plant growth regulators, and nucleic acids.
  • a disease control agent WO 2014/062775
  • a soil conditioner or a fertilizer as an active ingredient.
  • a method of mixing and using the compound of the present invention and other pesticides a method of formulating and using the compound of the present invention and another pesticide in one dosage form, both of which are formulated in separate dosage forms Are used before and after use, either using both formulated in separate dosage forms
  • Specific components contained in the fungicide which can be used by mixing with the compound of the present invention are exemplified by the following group b, and include salts, isomers and N-oxides thereof.
  • the known disinfectants are not limited to these.
  • Group b b-1: Phenylamide fungicide As a phenylamide fungicide, [b-1.1]: benalaxyl, [b-1.2] benalaxyl M or chiralaxyl (benalaxyl-M or kiralaxyl), [b [1.3] furalaxyl, [b-1.4] metalaxyl, [b-1.5] metalaxyl M or mefenoxam (metalaxyl-M or mefenoxam), [b-1.6] oxadixyl ( oxadixyl), [b-1.7] offurase, and the like.
  • b-2 Mitotic and mitosis inhibitor [b-2.1] benomyl, [b-2.2] carbendazim, [b- 2.3] Fuberidazole, [b-2.4] thiabendazole, [b-2.5] thiophanate, [b-2.6] thiophanate-methyl, [b- 2.7] Diethofencarb, [b-2,8] Zoxamide, [b-2.9] Ethaboxam, [b-2.10] Pencyclocurn, [b-2. 11] Fluopico Lido (fluopicolide), [b-2.12] phenamacril, and the like.
  • succinate dehydrogenase inhibitor As the succinate dehydrogenase inhibitors (SDHI agents), [b-3.1] benodanil, [b-3.2] benzovindiflupyr, [b-3.3] bixafen (bixafen) ), [B-3.4] boscarid, [b-3.5] carboxin, [b-3.6] fenfuram, [b-3.7] fluopyram , [B-3.8] flutolanil, [b-3.9] fluxapyroxad, [b-3.10] furamepyr, [b-3.11] isofetamid ), [B-3.12] isoprazam (isop) razam), [b-3.13] mepronil, [b-3.14] oxycarboxin, [b-3.15] penthiopyrad, [b-3.16] penflufen ( penflufen), [b-3.17] pydiflumetofen, [b-3.
  • SDHI agent succinate de
  • b-4 Quinone external inhibitor (QoI agent) [B-4.1] azoxystrobin, [b-4.2] cumoxystrobin, [b-4.3] dimoxyst as quinone external inhibitors (QoI agents) Robin (dimoxystrobin), [b-4.4] enoxastrobin, [b-4.5] Famoxadone, [b-4.6] fenamidone, [b-4.7] Phenaminestrobin, [b-4.8] flufenoxystrobin, [b-4.9] fluoxastrobin, [b-4.10] kresoxim-methyl hyl), [b-4.11] Mandestrobin, [b-4.12] Metominostrobin, [b-4.13] Orysastrobin, [b-4.14] Picoxystrobin, [b-4.15] pyraclostrobin, [b-4.16] pyramethostrobin, [b-4.17] pyraoxystrobin , [B-4.18] py
  • quinone internal inhibitor examples include [b-5.1] cyazofamid, [b-5.2] amisulbrom, and the like.
  • b-6 Oxidative phosphorylation uncoupling inhibitor
  • oxidative phosphorylation uncoupling inhibitor As the oxidative phosphorylation uncoupling inhibitor, [b-6.1] binapacryl, [b-6.2] meptyldinocap, [b-6.2] [b-6.3] dinocap, [b-6.4] fluazinam and the like.
  • b-7 Quinone external stigmatelin binding subsite inhibitor (QoSI agent) [B-7.1] amethoctrazine (Q-SI agent) includes quinone external stigmatelin binding subsite inhibitor.
  • b-8 amino acid biosynthesis inhibitor [b-8.1] cyprodinil, [b-8.2] mepanipyrim, [b-8.3] pyrimethanil as amino acid biosynthesis inhibitors ) And the like.
  • b-9 Protein biosynthesis inhibitor As a protein biosynthesis inhibitor, [b-9.1] streptomycin, [b-9.2] blasticidin-S, [b-9. 3] kasugamycin, [b-9.4] oxytetracycline and the like.
  • b-10 Signaling inhibitor As a signalling inhibitor, [b-10.1] fenpiclonil, [b-10.2] fludioxonil, [b-10.3] quinoxyfen, [B-10.4] proquinazide, [b-10.5] clozolinate, [b-10.6] dimethaclone, [b-10.7] iprodione, [b] -10.8] procymidone, [b-10.9] vinclozolin, and the like.
  • b-11 Lipid and cell membrane biosynthesis inhibitors As lipids and cell membrane biosynthesis inhibitors, [b-11.1] edifenphos, [b-11.2] iprobenfos, [b-11. 3] ] Pyrazophos, [b-11.4] isoprothiolane, [b-11.5] biphenyl, [b-11.6] chloroneb, [b-11.7] dichlorane (Dicloran), [b-11.8] quintogene, [b-11.
  • b-12 Demethylation inhibitor (DMI agent) As demethylation inhibitors (DMI agents), [b-12. 1] azaconazole, [b-12. 2] bitertanol, [b-12. 3] bromuconazole, [b-12.
  • b-13 Amine-based fungicide As an amine-based fungicide, [b-13.1] aldimorph, [b-13.2] dodemorph, [b-13.3] fenpropimorph ), [B-13.4] tridemorph, [b-13.5] fenpropidin, [b-13.6] piperaline, [b-13.7] spiroxamine ) And the like.
  • b-14 3-keto reductase inhibitor in C4-position demethylation of sterol biosynthesis
  • b-15 Squalene epoxidase inhibitor for sterol biosynthesis
  • a squalene epoxidase inhibitor for sterol biosynthesis [b-15.1] pyributicarb, [b-15.2] naftifine, [b -15.3] terbinafine and the like.
  • b-16 Cell wall biosynthesis inhibitor As a cell wall biosynthesis inhibitor, [b-16.1] polyoxins, [b-16.2] dimethomorph, [b-16.3] flumorph ( flumorph), [b-16.4] pyrimorph, [b-16.5] benthiavalicarb, [b-16.6] bentivaricarb-isopropyl, [b -16.7] iprovalicarb, [b-16.8] mandipropamide, [b-17.9] varifenalate, and the like.
  • b-17 melanin biosynthesis inhibitor
  • a melanin biosynthesis inhibitor As a melanin biosynthesis inhibitor, [b-17.1] fthalide (phthalide or phthalide), [b-17.2] pyroquilone, [b-17.3] tricyclazole (Triclazole), [b-17.4] carpropamide, [b-17.5] diclocymet, [b-17.6] fenoxanil, [b-17.7] tolprocarb (tolprocarb) ) And the like.
  • b-18 Host plant resistance inducer As host plant resistance inducer, [b-18.1] acibenzolar-S-methyl, [b-18.2] probenazole, [b] -18.3] thiadinil, [b-18.4] isotianil, [b-18.5] laminarin, and the like.
  • b-19 Dithiocarbamate fungicide [b-19.1] Mancozeb or manzeb (mancozeb or manzeb), [b-19.2] Maneb (maneb), [b-19.3] Methiram, [b-19.4] propineb, [b-19.5] thiuram, [b-19.6] zineb, [b-19.7] ziram (Ziram), [b-19.8] ferbam and the like.
  • b-20 Phthalimide fungicide [b-20.1] captan, [b-20.2] captafol, [b-20.3] folpet (folpet) ), [B-20.4] fluorophorpet and the like.
  • b-21 Guanidine fungicide As a guanidine fungicide, [b-21.1] guazatine, [b-21.2] iminoctadine, [b-21.3] iminoctadine albesilate (Iminoctadine albesilate), [b-21.4] iminoctadine triacetate and the like.
  • b-22 Multi-acting point contact active fungicide
  • b-23 Other fungicides [b-23.1] dichlobentiazox, [b-23.2] fenpicoxamide, [b-23.3] ] Dipymetitron, [b-23.4] bupirimate, [b-23.5] dimethylimol, [b-23.6] ethirimol, [b-23.7] acetic acid Triphenyltin (fentin acetate), [b-23.8] triphenyltin chloride (fentin chloride), [b-23.9] triphenyltin hydroxide (fentin hydroxide), [b-23.10] oxolinic acid (Oxo linic acid), [b-23.11] hymexazol, [b-23.12] octilinone, [b-23.13] fosetyl, [b-23.14] phosphorous acid (Phosphorous acid), [b-23.15] sodium salt of phosphorous acid (sodium phosphite), [b-
  • Equation (s1) See WO 98/046607)
  • Equation (s2) See WO 08/148570
  • Equation (s4) A compound represented by the following formula (see International Publication No. 12/084812):
  • Equation (s5) A compound (gougerotin) represented by
  • Equation (s6) A compound (ningnanmycin) represented by:
  • Equation (s7) See WO 10/136475)
  • Equation (s8) See WO 14/010737
  • Equation (s10) See WO 11/137002
  • Equation (s13) See WO09 / 156098
  • Equation (s16) [In the formula, A3 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a cyano group, and A4 represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 Represents a haloalkyl group or a C3-C8 cycloalkyl group. (See WO 14/095675),
  • Equation (s17) [Wherein, m1 represents an integer of 0 to 3, A5 and A6 each independently represent a halogen atom or a C1 to C6 alkyl group, A7 and A8 each independently represent Represents a halogen atom or a C1 to C6 alkoxy group, and when m1 is 2 or more, two or more A7s each represent an independent substituent, which may be the same or different. (See WO09 / 137538 and WO09 / 137651),
  • Equation (s18) [Wherein A9 and A10 are each independently a hydrogen atom or a halogen atom, A11 represents a halogen atom, A12 represents a halogen atom or an alkyl group of C1 to C6, and A13 represents , A halogen atom, a cyano group, a C1-C6 alkyl group, or a C1-C6 alkoxy group. (See WO 12/031061),
  • Equation (s19) [Wherein, m2 represents an integer of 0 to 6, A14 and A15 each independently represent a halogen atom, a cyano group, or a C1 to C6 alkyl group, and A16 represents a hydrogen atom, a halogen atom. Or A1 represents a C1 to C6 alkoxy group, A17 represents a halogen atom or a C1 to C6 alkoxy group, and when m2 is 2 or more, two or more A17 each represent an independent substituent, and May be different. (See WO 05/121104),
  • Equation (s20) [In the formula, A18 and A19 each independently represent a halogen atom, a cyano group, or a C1-C6 alkyl group; A20, A21 and A22 each independently represent a hydrogen atom, a halogen atom, Or a C1-C6 alkoxy group. (See WO07 / 066601),
  • Equation (s21) [In the formula, A23 and A24 are each independently a hydrogen atom, a halogen atom, a C1-C6 alkyl group or a C3-C8 cycloalkyl group, and X represents an oxygen atom or a sulfur atom. (See WO 07/087906, WO 09/016220, WO 10/130767),
  • Equation (s22) [In the formula, m3 represents an integer of 0 to 5, A25 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, Alternatively, when C3 to C8 are a cycloalkyl group, and m3 is 2 or more, two or more A25s each represent an independent substituent, which may be the same or different. (See WO 13/092224),
  • Equation (s23) [In the formula, A26 represents a hydrogen atom or a halogen atom, and V1 and V2 each independently represent an oxygen atom or a sulfur atom. ] (See WO 12/025450),
  • Equation (s24) or Equation (s25) [In the formula, m4 represents an integer of 0 to 5, A27 represents a C1 to C6 alkyl group, and A28 represents a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group. And when m4 is 2 or more, two or more A28s each represent an independent substituent and may be the same or different, and A29 is a C1-C6 alkyl group, a C2-C6 alkenyl group, or a C3 Represents an alkynyl group of -C6. ] (See WO 13/037771),
  • Equation (s26) or Equation (s27) [Wherein, m5 represents an integer of 0 to 5, A30 represents a C1 to C6 alkyl group, A31 represents a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group. And when m5 is 2 or more, two or more A31s each represent an independent substituent and may be the same or different, and A32 is a C1-C6 alkyl group, a C2-C6 alkenyl group, or a C3 Represents an alkynyl group of -C6. ] (See WO 13/037771),
  • Equation (s28) [Wherein, A33, A34, A35 and A36 each independently represent a hydrogen atom or a halogen atom, and A37 represents a hydrogen atom, an acetyl group or a benzoyl group. (See WO 06/031631, WO 10/069882),
  • Equation (s29) [In the formula, A38 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and A39 and A40 each independently represent a hydrogen atom or a halogen atom. ] (See WO 14/043376),
  • A41 represents a hydrogen atom, a hydroxyl group (—SH), a thiocyanate group (—SCN), or an alkylthio group of C1 to C6, and A42, A43, A44, and A45 are each independently , A hydrogen atom, or a halogen atom. (See WO 09/077443),
  • Group c c-1: Carbamate acetylcholinesterase (AChE) inhibitor As a carbamate acetylcholinesterase (AChE) inhibitor, [c-1.1] phosphocarb, [c-1.2] alanicarb, [c] -1.3] butoxycarboxym, [c-1.4] butoxycarboxim, [c-1.5] thiodicarb, [c-1.6] thiofanox ), [C-1.7] aldicarb, [c-1.8] bendiocarb, [c-1.9] benfuracarb, [c-1.10] carbaryl ryl), [c-1.11] carbofuran, [c-1.12] carbosulfan, [c-1.13] ethiofencarb, [c-1.14] fenobcarb ( fenobucarb, [c-1.15] formetanate, [c-1.16] furathiocarb, [c-1.17] isoprocar
  • c-2 Organophosphorus acetylcholinesterase (AChE) inhibitor
  • Azinphos-methyl [c-2.4] Azinphos-ethyl, [c-2.5] Ethephon, [c-2.6] ] Cadusafos, [c-2.7] chlorethoxyphos, [c-2.8] chlorfenvinphos, [c-2.9] chlormephos, [c- 2.10] black Lupyrifos (chlorpyrifos), [c-2.11] Chlorpyrifos-methyl, [c-2.12] Coumaphos, [c-2.13] Cyanophos, [c-2.
  • c-3 GABA-operated chloride channel blocker [c-3.1] chlordane, [c-3.2] endosulfan, [c-3.3] as GABA-operated chloride channel blockers. ] Lindane, [c-3.4] dienochlor, [c-3.5] ethiprole, [c-3.6] fipronil, [c-3.7] aceto Aceproprole and the like.
  • c-4 Sodium channel modulator As a sodium channel modulator, [c-4.1] acrinathrin, [c-4.2] arethrin [(1R) -isomer] (allethrin [(1R) -isomer]), [C-4.3] bifenthrin, [c-4.4] bioallethrin, [c-4.5] bioallethrin S-cyclopentenyl isomer (bioallthrin S-cyclopentenyl isomer), [-c- 4.6] bioresmethrin, [c-4.7] cycloprothrin, [c-4.8] cyfluthrin, [c-4.
  • c-5 Nicotinic Acetylcholine Receptor (nAChR) Competitive Modulator As a nicotinic acetylcholine receptor (nAChR) competitive modulator, [c-5.1] acetamipride (acetamiprid), [c-5.2] clothianidin (clothianidin) ), [C-5.3] dinotefuran, [c-5.4] imidacloprid, [c-5.5] nitenpyram, [c-5.6] thiacloprid, [C-5.7] thiamethoxam, [c-5.8] nicotine, [c-5.9] nicotine sulfate, [c-5.10] sulphate Kisafuroru (sulfoxaflor), [c-5.11] Furupirajifuron (flupyradifurone), and the like [c-5.12] triflupromazine meso pyridinium beam (triflumezopyrim).
  • nAChR Nicotin
  • c-6 Nicotinic acetylcholine receptor (nAChR) allosteric modulator As a nicotinic acetylcholine receptor (nAChR) allosteric modulator, [c-6.1] spinosad (spinosad), [c-6.2] spinetoram, etc. Is mentioned.
  • c-7 Glutamergic chloride channel (GluCl) allosteric modulator As a glutamate-gated chloride ion channel (GluCl) allosteric modulator, [c-7.1] abamectin, [c-7.2] emamectin benzoate Salt (emmectin benzoate), [c-7.3] lepimectin, [c-7.4] milbemectin, and the like.
  • GluCl glutamate-gated chloride ion channel
  • c-8 Juvenile hormone analogs As juvenile hormone analogs, [c-8.1] hydroprene, [c-8.2] quinoprene, [c-8.3] methoprene ), [C-8.4] phenoxycarb, [c-8.5] pyriproxyfen, and the like.
  • c-9 Non-specific (multi-site) inhibitor
  • a non-specific (multi-site) inhibitor As a non-specific (multi-site) inhibitor, [c-9.1] methyl bromide, [c-9.2] chloropicrin , [C-9.3] cryolite, [c-9.4] sulfuryl fluoride, [c-9.5] borax, [c-9.6] borane Acid (boric acid), [c-9.7] disodium octaborate, [c-9.8] sodium metaborate [c-9.9] tartar emetic), [c-9.10] dazomet, [c-9.11] metham (m etam), [c-9.12] carbam sodium salt and the like.
  • c-10 String Organ TRPV Channel Modulator
  • Examples of the string organ TRPV channel modulator include [c-10.1] pymetrozine, [c-10.2] pyrifluquinazone, and the like.
  • c-11 Mite growth inhibitor As mite growth inhibitors, [c-11. 1] clofentezine, [c-11. 2] diflovidazin, [c-11. (Hexythiazox), [c-11.4] ethoxazole, and the like.
  • c-12 Mitochondrial ATP synthase inhibitor As a mitochondrial ATP synthase inhibitor, [c-12. 1] diafenthiuron, [c-12. 2] azocyclotin, [c-12. 3] cyhexatin, [c-12.4] fenbutatin oxide, "c-12.5" propargite, "c-12.6” tetradifon, and the like. .
  • c-13 Oxidative phosphorylation uncoupling agent that disrupts the proton gradient
  • oxidative phosphorylation uncoupler that disrupts the proton gradient
  • c-14 Nicotinic acetylcholine receptor (nAChR) channel blocker [c-14.1] bensultap, [c-14.2] cartap hydrochloride (cartap) as a nicotinic acetylcholine receptor (nAChR) channel blocker hydrochloride, [c-14.3] thiocyclam, [c-14.4] monosultap, and the like.
  • c-15 chitin biosynthesis inhibitor type 0 As chitin biosynthesis inhibitor type 0, [c-15.1] bistrifluron, [c-15.2] chlorfluazuron, [c-15.3] diflubenzuron, [C-15.4] flucycloxuron, [c-15.5] flufenoxuron, [c-15.6] hexaflumuron, [c-15.7] Lufenuron, [c-15.8] novaluron, [c-15.9] noviflumuron, [c-15.10] teflubenzuron, [c-15.11] Rifurumuron (triflumuron), and the like.
  • c-16 Chitin biosynthesis inhibitor type 1
  • Examples of the chitin biosynthesis inhibitor type 1 include [c-16.1] buprofezin and the like.
  • c-17 Inhibitor of moltid insect molting
  • insect molting inhibitor of the order Streptococcus [c-17.1] cyromazine and the like can be mentioned.
  • c-18 molting hormone (ecdysone) receptor agonist
  • a molting hormone (ecdysone) receptor agonist [c-18.1] chromafenozide, [c-18.2] halofenozide, [c-18] .3] methoxyphenozide, [c-18.4] tebufenozide and the like.
  • Octopamine receptor agonist examples include [c-19.1] amitraz.
  • c-20 mitochondrial electron transfer complex III inhibitor [c-20.1] hydramethylnon, [c-20.2] acequinocyl, [C-20.3] fluacryliprim, [c-20.4] bifenazate, and the like.
  • c-21 Mitochondrial electron transport complex I inhibitor (METI) [C-21.1] fenazaquin, [c-21.2] fenpyroximate, [c-21.3] pyridaben, as mitochondrial electron transport system complex I inhibitors (METI); [C-21.4] pyrimidifen, [c-21.5] tebufenpyrad, [c-21.6] tolfenpyrad, [c-21.7] rotenone, and the like.
  • MEI Mitochondrial electron transport complex I inhibitor
  • c-22 Voltage-dependent sodium channel blocker
  • Examples of the voltage-dependent sodium channel blocker include [c-22.1] indoxacarb, [c-22.2] metaflumizone, and the like.
  • c-23 Acetyl-CoA carboxylase inhibitor As an acetyl-CoA carboxylase inhibitor, [c-23.1] spirodiclofen, [c-23.2] spiromesifen, [c-23.3] ] Spirotetramat and the like.
  • c-24 Mitochondrial electron transport system complex IV inhibitor [c-24.1] aluminum phosphide (aluminum phosphide), [c-24.2] calcium phosphate ( calcium phosphate, [c-24.3] hydrogen phosphide (phosphine), [c-24.4] zinc phosphide (zinc phosphide), [c-24.5] calcium cyanide, [c ⁇ 24.6] sodium cyanide (potassium cyanide), [c-24.7] potassium cyanide, and the like.
  • c-25 mitochondrial electron transport system complex II inhibitor [c-25.1] cyenopyrafen, [c-25.2] cyflumetofen, [c-25.1] cyenopyrafen -25.3] piflubumide and the like.
  • c-26 Ryanodine receptor modulator As the ryanodine receptor modulator, [c-26.1] chlorantraniliprole, [c-26.2] cyanantraniprole, [c-26. 3] flubendiamide and the like.
  • c-28 Other insecticides [c-28.1] azadirachtin, [c-28.2] benzoximate, [c-28.3] phenisobromo Phenisobromolate, [c-28.4] quinomethionate, [c-28.5] dicofol, [c-28.6] pyridalyl, [c-28.7] bromopropylate Brompropylate, [c-28.8] triazamate, [c-28.9] dicyclanil, [c-28.10] dinobuton, [c-28.11] dinocup ( din ocap), [c-28.12] hydrogen cyanide, [c-28.13] methyl iodide, [c-28.14] Karanjin, [c-28.15] Mercury chloride, [c-28.16] methyl isothiocyanate, [c-28.17] pentachlorophenol, [c-28.18] phosphin
  • Equation (s36) A compound represented by the formula (see International Publication No. 12/029672):
  • Equation (s42) [In the formula, m7 represents an integer of 0 to 2. (See WO 11/152320),
  • Equation (s43) [In the formula, m8 represents an integer of 0 to 2. ] (See JP-A-27-160813);
  • Equation (s44) [Wherein, A52 represents a hydrogen atom or a fluorine atom. (See WO 11/134964, WO 14/005982),
  • Equation (s45) [In the formula, m9 represents an integer of 0 to 2, and A53 represents a fluorine atom or a chlorine atom. (See WO 15/025826),
  • Equation (s46) [Wherein, V3 represents a nitrogen atom, a carbon atom, or CF, and V4 and V5 each independently represent a nitrogen atom or a carbon atom. (See WO 11/134964, WO 14/005982),
  • Equation (s49) [Wherein, A59 represents a hydrogen atom, a fluorine atom, or a chlorine atom; Represents a partial structure selected from the group consisting of (See WO 10/090344),
  • Formula (s50) [In the formula, m10 represents an integer of 0 to 2, A61 represents a trifluoromethyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, and A62 represents a hydrogen atom or Represents a trifluoromethyl group, V6 represents a nitrogen atom or a carbon atom, and V7 represents an oxygen atom or an N-methyl group. (See WO 14/104407),
  • Equation (s51) [Wherein, A63 represents a hydrogen atom or a fluorine atom, the amide group is bonded to the 4- or 5-position, and A64 is Represents a partial structure selected from the group consisting of (See WO 15/038503, WO 16/144351, WO 16/144678),
  • Equation (s52) [Wherein, A65 represents a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group, A66 represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group, and A67 and A68 represent Each independently being a hydrogen atom, a C1-C6 alkyl group optionally substituted with a cyano group, an alkyl group optionally substituted with a methoxy group, an alkyl group optionally substituted with an ethoxy group, Or a C3-C8 cycloalkyl group, A69 represents a hydrogen atom, a cyano group, a C1 to C6 haloalkyl group optionally substituted with a cyano group, a C1 to C6 alkyl group, or a C3 to C8 cycloalkyl group. (See WO 12/143317, WO
  • a 70 represents a methyl group, an ethyl group, an isopropyl group, a 2,2,2-trifluoroethyl group, or a phenyl group
  • A72 represents a partial structure selected from the group consisting of:
  • V8 represents an oxygen atom, a sulfur atom, —CH 2 —, or —CH 2 CH 2 —.
  • Equation (s55) [Wherein, m11 represents an integer of 0 to 1, A73 represents a chlorine atom, a bromine atom, a methyl group, or a trifluoromethyl group, A74 represents a hydrogen atom, a chlorine atom, a bromine atom, a cyano group, A75 represents a hydrogen atom, a chlorine atom or a bromine atom; A76 and A77 each independently represent a C1-C6 alkyl group or a C3-C8 cycloalkyl group; A78 represents a chlorine atom, a bromine atom, a cyano group, a nitro group, a difluoromethyl group, or a trifluoromethyl group.
  • Formula (s56) [Wherein A79, A80, A81 and A82 are each independently a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, or a C3-C8 Represents a cycloalkoxy group. (See WO 12/027521),
  • Equation (s57) [In the formula, m12 represents an integer of 0 to 2, A83 represents a hydrogen atom or a fluorine atom, and A84 represents Represents a partial structure selected from the group consisting of (See WO 13/162715),
  • Equation (s59) [A90 represents a halogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group, A91 represents a C1-C6 haloalkyl group, A92 and A93 each independently represent a hydrogen atom, Represents a C1-C6 alkyl group, an acetyl group, a propionoyl group, a methanesulfonylethyl group, a methoxycarbonyl group, or an ethoxycarbonyl group, and A94 and A95 are each independently a hydrogen atom, a C1-C6 alkyl group, Or a C1-C6 haloalkyl group. And the like (see WO 12/1664698).
  • the mixing ratio of the compound of the present invention and other agrochemicals that can be used by mixing as necessary as described above is not particularly limited as long as the effect is exerted.
  • Other pesticides have a weight ratio of 0.001 to 1000, preferably 0.01 to 100.
  • Step 2 Synthesis of 1-ethyl-6- (4-fluorophenyl) -5- (thiophen-3-yl) -3,4-dihydropyridin-2 (1H) -one
  • Step 3 Synthesis of 5- (2-bromothiophen-3-yl) -1-ethyl-6- (4-fluorophenyl) -3,4-dihydropyridin-2 (1H) -one (Compound No .: 4)
  • Table 4 shows compounds synthesized according to the above-mentioned Examples, but the present invention is not limited to these.
  • Structure A shows the following.
  • Structure B shows the following.
  • Structure C shows the following.
  • Structure D shows the following.
  • Table 1 shows their 1 H-NMR data.
  • the compounds of the present invention are specifically shown to be effective against plant diseases, but are not limited to these examples.
  • the cells were allowed to stand in a wet room at room temperature of 20 to 23 ° C. for about 24 hours to promote the onset of the disease.
  • the onset of disease 6 to 10 days after inoculation was investigated, and the effect of the drug solution was evaluated.
  • Tomato gray mold A seed of a test plant (tomato variety: large fukuju) was sown, and then cultivated until 3 to 5 true leaves developed.
  • the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution.
  • the obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the chemical solution was dried, the plants were spray-inoculated with a conidia suspension of Botrytis cinerea at 4 to 8 ⁇ 10 5 cells / ml.
  • the cells were allowed to stand in a wet room at room temperature of 20 to 23 ° C. for about 48 hours to promote the onset of the disease.
  • the onset of disease 2-3 days after inoculation was investigated, and the effect of the drug solution was evaluated.
  • Test Example C Cabbage black spot disease Seeds of a test plant (cabbage variety: four seasons harvest) were sown and then cultivated until cotyledons developed.
  • the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution.
  • the obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the chemical solution was dried, the plants were spray-inoculated with a conidia suspension of 4-8 ⁇ 10 5 cells / ml of cabbage black rot fungus (Alternia brassicicola).
  • the cells were allowed to stand in a wet room at room temperature of 20 to 23 ° C. for about 48 hours to promote the onset of the disease.
  • the onset of disease 2-3 days after inoculation was investigated, and the effect of the drug solution was evaluated.
  • Test Example D Barley powdery mildew Seeds of a test plant (barley variety: Akagami Riki) were sown and then cultivated until the first leaves were developed.
  • the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution.
  • the obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the chemical solution was dried, the conidia of barley powdery mildew (Blumeria graminis f.sp.hordei) were beaten and inoculated to the plants. 6 to 10 days after the inoculation, the degree of onset was investigated, and the effect was evaluated.
  • Test Example E Wheat leaf rust Seeds of a test plant (wheat variety: Norin 61) were sown and then cultivated until the first leaves developed.
  • the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution.
  • the obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the medicinal solution was dried, the plants were spray-inoculated with a uredospore suspension of 1-2 ⁇ 10 5 cells / ml of wheat leaf rust (Puccinia recondita).
  • the cells were allowed to stand in a wet room at room temperature of 20 to 23 ° C. for about 24 hours to promote the onset of the disease.
  • the onset of disease 7 to 10 days after inoculation was investigated, and the effect of the drug solution was evaluated.
  • Tomato late blight Seeds of a test plant (tomato variety: large fukuju) were sown, and then cultivated until three to five true leaves were developed.
  • the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution.
  • the obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the chemical solution was dried, the plants were spray-inoculated with a zoospore suspension of 4 to 8 ⁇ 10 3 cells / ml of Phytophthora infestans.
  • the cells were left in a wet room at room temperature of 20 ° C. for about 24 hours to promote the onset of the disease.
  • the disease onset 5 to 10 days after the inoculation was investigated, and the effect of the drug solution was evaluated.
  • Test Example G Grape downy mildew Seeds of a test plant (grape variety: Neo Muscat) were sown, and then cultivated until three to four true leaves were developed.
  • the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution.
  • the obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the medicinal solution was dried, the plants were spray-inoculated with a zoospore suspension of Plasmopara viticola at 1-2 ⁇ 10 4 cells / ml.
  • the cells were left in a wet room at room temperature of 20 ° C. for about 24 hours to promote the onset of the disease.
  • the onset of disease 7 to 10 days after inoculation was investigated, and the effect of the drug solution was evaluated.
  • Test Example H Cucumber Anthrax Disease Seeds of a test plant (cucumber variety: Sagami Hanjiro) were sown, and then cultivated until one true leaf developed.
  • the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution.
  • the obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the medicinal solution was dried, the plants were spray-inoculated with a conidia spore suspension of 2 to 4 ⁇ 10 5 cells / ml of cucumber anthrax (Colletotrichum orbiculare).
  • the cells were allowed to stand in a wet room at room temperature of 20 to 23 ° C. for about 24 hours to promote the onset of the disease.
  • the onset of disease 6 to 10 days after inoculation was investigated, and the effect of the drug solution was evaluated.
  • the degree of disease was evaluated for each 0.05, with the degree of disease occurring in uninfected plants being 0 and the degree of disease occurring in plants in the non-treated area being set to 3. Further, the control value was calculated from the degree of onset according to the following formula.
  • H indicates that the control value is greater than 50%
  • L indicates that the control value is 50% or less.
  • nt indicates that the test was not performed.
  • the compound of the present invention is a novel compound and can control plant diseases, and therefore has a value as a pesticide, for example, a pesticide for agricultural and horticultural use, particularly a fungicide for agricultural and horticultural use.

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  • Hydrogenated Pyridines (AREA)

Abstract

The purpose of the present invention is in order to provide a novel compound which is effective as an agricultural and horticultural fungicide. This compound is a compound represented by formula (1) or a salt thereof [in the formula, R1 represents a hydroxyl group, a cyano group, etc., R2, R3 and R4 independently represent a hydrogen atom, a halogen atom, etc., R5 represents a hydrogen atom, a halogen atom, etc., X represents an oxygen atom or a sulfur atom, Y represents formula (y-1) or formula (y-2), R6 represents a halogen atom, etc., and the bond including a broken line segment represents a double bond or a single bond], and this pesticide for agricultural and horticultural use contains said compound as an active component.

Description

ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤Pyridone compounds and fungicides for agricultural and horticultural use containing the same as active ingredients
　本発明は、ピリドン化合物および該化合物を有効成分とする農薬に関するものである。 The present invention relates to a pyridone compound and an agricultural chemical containing the compound as an active ingredient.
　安定的な農業生産を確保する上で、農園芸作物の病害を防除することは重要な役割を果たす。そのため、様々な殺菌剤が使用されているが、長年にわたる殺菌剤の使用は薬剤耐性菌の出現を招くために、薬剤感受性菌のみならず薬剤耐性菌に対しても有効な新規殺菌剤が切望されている。 防 Controlling the disease of agricultural and horticultural crops plays an important role in ensuring stable agricultural production. For this reason, various fungicides have been used, but the use of fungicides over the years has led to the emergence of drug-resistant bacteria. Have been.
　ところで、１，３，５，６－置換－２－ピリドン化合物に関して、例えば、ＧＡＢＡアルファー２／３リガンドとして、３位にアリール基またはヘテロアリール基を有する１，３，５，６－置換－２－ピリドン化合物が開示されている（例えば、国際公開第９８／５５４８０号参照）。また、細菌性感染症の治療薬として、３位にカルボキシル基を有する１，３，５，６－置換－２－ピリドン化合物が開示されている（例えば、欧州特許第０３０８０２０明細書参照）。 By the way, regarding 1,3,5,6-substituted-2-pyridone compounds, for example, 1,3,5,6-substituted-2 compounds having an aryl group or a heteroaryl group at the 3-position as GABA alpha-2 / 3 ligand -Pyridone compounds have been disclosed (see, for example, WO 98/55480). Further, as a therapeutic agent for bacterial infection, a 1,3,5,6-substituted-2-pyridone compound having a carboxyl group at the 3-position has been disclosed (see, for example, European Patent No. 0308020).
国際公開第９８／５５４８０号International Publication No. 98/55480 欧州特許第０３０８０２０明細書European Patent No. 0308020
　しかしながら、国際公開第９８／５５４８０号および欧州特許第０３０８０２０明細書に記載されている化合物の用途は、いずれも医薬に関するものであり、本発明に係る農園芸用殺菌剤が属する技術分野とは相違する。 However, the uses of the compounds described in WO 98/55480 and EP 0 308 020 are all related to medicine, which is different from the technical field to which the agricultural and horticultural fungicides according to the present invention belong. I do.
　本発明の課題は、農園芸用殺菌剤として有効である新規な化合物を提供することである。 課題 An object of the present invention is to provide a novel compound which is effective as an agricultural and horticultural fungicide.
　本発明者らは、前記課題を解決すべく、１，３，５，６－置換－２－ピリドン化合物群および１，５，６－置換－２－ピリドン化合物群について鋭意検討を行った結果、当該２－ピリドン骨格中の５位に関して、適宜置換されてもよいチオフェン－２－イル基または適宜置換されてもよいチオフェン－３－イル基を導入した新規な化合物群が、植物病害に対して優れた防除活性を発揮することを見出し、本発明を完成するに至った。 The present inventors have conducted intensive studies on the 1,3,5,6-substituted-2-pyridone compound group and the 1,5,6-substituted-2-pyridone compound group in order to solve the above problems. Regarding the 5-position in the 2-pyridone skeleton, a novel group of compounds in which an optionally substituted thiophen-2-yl group or an optionally substituted thiophen-3-yl group has been introduced, against a plant disease They have found that they exert excellent control activity, and have completed the present invention.
　すなわち、本発明は、以下の通りである。
［１］
　式（１）
Figure JPOXMLDOC01-appb-C000005
　［式中、Ｒ１は、
　　水酸基、
　　シアノ基、
　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　　Ｃ１～Ｃ６のハロアルキル基、
　　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　　Ｃ２～Ｃ６のハロアルケニル基、
　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　　Ｃ２～Ｃ６のハロアルキニル基、
　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　　Ｃ１～Ｃ６のハロアルコキシ基、
　　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
　　置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
　　またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表し；
　Ｒ２、Ｒ３およびＲ４は、それぞれ独立していて、
　　水素原子、
　　ハロゲン原子、
　　水酸基、
　　シアノ基、
　　ニトロ基、
　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　　Ｃ１～Ｃ６のハロアルキル基、
　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　　Ｃ２～Ｃ６のハロアルケニル基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　　Ｃ２～Ｃ６のハロアルキニル基、
　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　　Ｃ１～Ｃ６のハロアルコキシ基、
　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
　　置換基Ｄで適宜０～５置換されてもよいアリールオキシ基、
　　置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基、
　　置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、
　　Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表す。）、
　　Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、前記と同義である。）、
　　１～２個の酸素原子を含む３～６員環の基、
　　Ｒｃ－Ｌ－（ここで、Ｒｃは、Ｃ１～Ｃ６のアルキル基またはＣ１～Ｃ６のハロアルキル基を表し、Ｌは、Ｓ、ＳＯ、またはＳＯ２を表す。）、
　　ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
　　またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表し、Ｒｘ３は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。）を表し；
　Ｒ５は、
　　水素原子、
　　ハロゲン原子、
　　シアノ基、
　　ニトロ基、
　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　　Ｃ１～Ｃ６のハロアルキル基、
　　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　　Ｃ２～Ｃ６のハロアルケニル基、
　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　　Ｃ２～Ｃ６のハロアルキニル基、
　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　　Ｃ１～Ｃ６のハロアルコキシ基、
　　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
　　置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
　　Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
　　ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
　　またはＲ５１Ｃ（＝Ｏ）－（ここで、Ｒ５１は、水酸基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、またはＣ１～Ｃ６のアルコキシ基を表す。）を表し；
　Ｘは、酸素原子または硫黄原子を表し；
　Ｙは、式（ｙ－１）、または式（ｙ－２）
Figure JPOXMLDOC01-appb-C000006
を表し、
　Ｒ６は、
　　ハロゲン原子、
　　水酸基、
　　シアノ基、
　　ニトロ基、
　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　　Ｃ１～Ｃ６のハロアルキル基、
　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　　Ｃ２～Ｃ６のハロアルケニル基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　　Ｃ２～Ｃ６のハロアルキニル基、
　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　　Ｃ１～Ｃ６のハロアルコキシ基、
　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
　　置換基Ｄで適宜０～５置換されてもよいアリールオキシ基、
　　置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基、
　　置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、
　　Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、前記と同義である。）、
　　Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、前記と同義である。）、
　　１～２個の酸素原子を含む３～６員環の基、
　　Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
　　ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
　　またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２およびＲｘ３は、前記と同義である。）を表し；
　ｎは、０～３の整数（ｎが２以上の場合、２以上のＲ６はそれぞれ独立した置換基を表す。）を表し；
　破線部を含む結合は、二重結合、または単結合を表し；
　そして、置換基Ａは、水酸基、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）およびＲｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）からなる群から選択される少なくとも１種であり；
　置換基Ｂは、シアノ基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種であり；
　置換基Ｃは、水酸基、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、Ｃ２～Ｃ６のアルコキシアルコキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、ＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記のＲｘ１と同義である。）および１～２個の酸素原子を含む３～６員環の基からなる群から選択される少なくとも１種であり；
　置換基Ｄは、ハロゲン原子、水酸基、シアノ基、ニトロ基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種である。］で表される化合物、またはその塩。 That is, the present invention is as follows.
[1]
Equation (1)
Figure JPOXMLDOC01-appb-C000005
Wherein R1 is
Hydroxyl group,
Cyano group,
A C1-C6 alkyl group optionally substituted with a substituent A,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent A,
A C2-C6 alkenyl group optionally substituted with a substituent A,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent A,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with a substituent A,
C1-C6 haloalkoxy groups,
A C3-C8 cycloalkoxy group optionally substituted with a substituent A,
A C2-C6 alkenyloxy group optionally substituted with a substituent A,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent A,
A C3-C6 haloalkynyloxy group,
Or RaRbN- (where Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 Represents a cycloalkyl group, or Ra and Rb represent, together with the nitrogen atom to be bound, an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group. Represent;
R2, R3 and R4 are each independently;
Hydrogen atom,
Halogen atom,
Hydroxyl group,
Cyano group,
Nitro group,
A C1-C6 alkyl group optionally substituted with a substituent C,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent C,
A C2-C6 alkenyl group optionally substituted with a substituent C,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent C,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with a substituent C,
C1-C6 haloalkoxy groups,
A C3-C8 cycloalkoxy group optionally substituted with a substituent C,
A C2-C6 alkenyloxy group optionally substituted with a substituent C,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent C,
A C3-C6 haloalkynyloxy group,
An aryloxy group optionally substituted with 0 to 5 substituents D,
A heteroaryloxy group optionally substituted with 0 to 2 substituents D,
An aralkyloxy group optionally substituted with 0 to 5 substituents D,
Rx1C (= O)-(where Rx1 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group which may be appropriately substituted with a substituent B A group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as described above),
Rx1C (= O) O- (where Rx1 is as defined above),
A 3-6 membered ring group containing 1-2 oxygen atoms,
Rc-L-(wherein, Rc represents a haloalkyl group of alkyl or C1 ~ C6 of C1 ~ C6, L represents S, SO, or SO 2.),
RaRbN- (where Ra and Rb are as defined above),
Or Rx2C (= O) N (Rx3)-(where Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl Represents an alkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN— (where Ra and Rb have the same meanings as described above), and Rx3 represents , A hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be optionally substituted with a substituent B);
R5 is
Hydrogen atom,
Halogen atom,
Cyano group,
Nitro group,
A C1-C6 alkyl group optionally substituted with a substituent A,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent A,
A C2-C6 alkenyl group optionally substituted with a substituent A,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent A,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with a substituent A,
C1-C6 haloalkoxy groups,
A C3-C8 cycloalkoxy group optionally substituted with a substituent A,
A C2-C6 alkenyloxy group optionally substituted with a substituent A,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent A,
A C3-C6 haloalkynyloxy group,
Rc-L- (where Rc and L are as defined above),
RaRbN- (where Ra and Rb are as defined above),
Or R51C (＝ O)-(where R51 is a hydroxyl group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, or a C1 Represents an alkoxy group of -C6);
X represents an oxygen atom or a sulfur atom;
Y is the formula (y-1) or the formula (y-2)
Figure JPOXMLDOC01-appb-C000006
Represents
R6 is
Halogen atom,
Hydroxyl group,
Cyano group,
Nitro group,
A C1-C6 alkyl group optionally substituted with a substituent C,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent C,
A C2-C6 alkenyl group optionally substituted with a substituent C,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent C,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with a substituent C,
C1-C6 haloalkoxy groups,
A C3-C8 cycloalkoxy group optionally substituted with a substituent C,
A C2-C6 alkenyloxy group optionally substituted with a substituent C,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent C,
A C3-C6 haloalkynyloxy group,
An aryloxy group optionally substituted with 0 to 5 substituents D,
A heteroaryloxy group optionally substituted with 0 to 2 substituents D,
An aralkyloxy group optionally substituted with 0 to 5 substituents D,
Rx1C (= O)-(where Rx1 is as defined above),
Rx1C (= O) O- (where Rx1 is as defined above),
A 3-6 membered ring group containing 1-2 oxygen atoms,
Rc-L- (where Rc and L are as defined above),
RaRbN- (where Ra and Rb are as defined above),
Or Rx2C (= O) N (Rx3)-(where Rx2 and Rx3 are as defined above);
n represents an integer of 0 to 3 (when n is 2 or more, 2 or more R6 each represents an independent substituent);
A bond containing a broken line represents a double bond or a single bond;
The substituent A is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, RaRbN- (where Ra And Rb are as defined above, and Rc-L- (wherein Rc and L are as defined above), and are at least one selected from the group consisting of:
Substituent B is at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group;
Substituent C is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN -(Where Ra and Rb are as defined above), Rc-L- (where Rc and L are as defined above), RdC (= O)-(where Rd Is the same as defined above for Rx1), and is at least one member selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Substituent D is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C8 It is at least one selected from the group consisting of a C6 alkoxy group, a C1 to C6 haloalkoxy group and a C3 to C8 cycloalkoxy group. Or a salt thereof.
［２］
　Ｒ１は、
　　シアノ基、
　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　　Ｃ１～Ｃ６のハロアルキル基、
　　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　　Ｃ２～Ｃ６のハロアルケニル基、
　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　　またはＣ２～Ｃ６のハロアルキニル基を表し；
　Ｒ２、Ｒ３およびＲ４は、それぞれ独立していて、
　　水素原子、
　　ハロゲン原子、
　　水酸基、
　　シアノ基、
　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　　Ｃ１～Ｃ６のハロアルキル基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　　Ｃ１～Ｃ６のハロアルコキシ基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
　　置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、
　　またはＲｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表す。）を表し；
　Ｒ５は、
　　水素原子、
　　ハロゲン原子、
　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　　Ｃ１～Ｃ６のハロアルキル基、
　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
　　置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
　　またはＲ５１Ｃ（＝Ｏ）－（ここで、Ｒ５１は、水酸基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、またはＣ１～Ｃ６のアルコキシ基を表す。）を表し；
　Ｒ６は、
　　ハロゲン原子、
　　水酸基、
　　シアノ基、
　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　　Ｃ１～Ｃ６のハロアルキル基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　　Ｃ１～Ｃ６のハロアルコキシ基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
　　Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、前記と同義である。）、
　　Ｒｃ－Ｌ－（ここで、Ｒｃは、Ｃ１～Ｃ６のアルキル基またはＣ１～Ｃ６のハロアルキル基を表し、Ｌは、Ｓ、ＳＯ、またはＳＯ２を表す。）、
　　またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表す、［１］に記載の化合物、またはその塩。 [2]
R1 is
Cyano group,
A C1-C6 alkyl group optionally substituted with a substituent A,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent A,
A C2-C6 alkenyl group optionally substituted with a substituent A,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent A,
Or a C2-C6 haloalkynyl group;
R2, R3 and R4 are each independently;
Hydrogen atom,
Halogen atom,
Hydroxyl group,
Cyano group,
A C1-C6 alkyl group optionally substituted with a substituent C,
A C1-C6 haloalkyl group,
A C2-C6 alkenyl group optionally substituted with a substituent C,
A C2-C6 alkynyl group optionally substituted with a substituent C,
A C1-C6 alkoxy group optionally substituted with a substituent C,
C1-C6 haloalkoxy groups,
A C2-C6 alkenyloxy group optionally substituted with a substituent C,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent C,
A C3-C6 haloalkynyloxy group,
An aralkyloxy group optionally substituted with 0 to 5 substituents D,
Or Rx1C (＝ O) O— (where Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 , A C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN— (where Ra and Rb are each independently a hydrogen atom or a substituent B, It represents a good C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb together with the nitrogen atom to be bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl , A piperidinyl group, a homopiperidinyl group, or an azocanyl group.).
R5 is
Hydrogen atom,
Halogen atom,
A C1-C6 alkyl group optionally substituted with a substituent A,
A C1-C6 haloalkyl group,
A C2-C6 alkenyl group optionally substituted with a substituent A,
A C2-C6 alkynyl group optionally substituted with a substituent A,
A C1-C6 alkoxy group optionally substituted with a substituent A,
A C2-C6 alkenyloxy group optionally substituted with a substituent A,
A C3-C6 alkynyloxy group optionally substituted with a substituent A,
Or R51C (＝ O)-(where R51 is a hydroxyl group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, or a C1 Represents an alkoxy group of -C6);
R6 is
Halogen atom,
Hydroxyl group,
Cyano group,
A C1-C6 alkyl group optionally substituted with a substituent C,
A C1-C6 haloalkyl group,
A C2-C6 alkenyl group optionally substituted with a substituent C,
A C2-C6 alkynyl group optionally substituted with a substituent C,
A C1-C6 alkoxy group optionally substituted with a substituent C,
C1-C6 haloalkoxy groups,
A C2-C6 alkenyloxy group optionally substituted with a substituent C,
A C3-C6 alkynyloxy group optionally substituted with a substituent C,
Rx1C (= O)-(where Rx1 is as defined above),
Rc-L-(wherein, Rc represents a haloalkyl group of alkyl or C1 ~ C6 of C1 ~ C6, L represents S, SO, or SO 2.),
Or the compound or salt thereof according to [1], representing RaRbN- (where Ra and Rb are as defined above).
［３］
　Ｒ１は、
　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　　またはＣ１～Ｃ６のハロアルキル基を表し；
　Ｒ２、Ｒ３およびＲ４は、それぞれ独立していて、
　　水素原子、
　　ハロゲン原子、
　　水酸基、
　　シアノ基、
　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　　または置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基を表し；
　Ｒ５は、
　　水素原子、
　　ハロゲン原子、
　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　　Ｃ１～Ｃ６のハロアルキル基、
　　または置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基を表し；
　Ｒ６は、
　　ハロゲン原子、
　　シアノ基、
　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　　Ｃ１～Ｃ６のハロアルキル基、
　　または置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基を表す、［２］に記載の化合物、またはその塩。 [3]
R1 is
A C1-C6 alkyl group optionally substituted with a substituent A,
Or a C1-C6 haloalkyl group;
R2, R3 and R4 are each independently;
Hydrogen atom,
Halogen atom,
Hydroxyl group,
Cyano group,
A C1-C6 alkyl group optionally substituted with a substituent C,
Or a C1-C6 alkoxy group optionally substituted with a substituent C;
R5 is
Hydrogen atom,
Halogen atom,
A C1-C6 alkyl group optionally substituted with a substituent A,
A C1-C6 haloalkyl group,
Or a C2-C6 alkynyl group optionally substituted with a substituent A;
R6 is
Halogen atom,
Cyano group,
A C1-C6 alkyl group optionally substituted with a substituent C,
A C1-C6 haloalkyl group,
Or the compound according to [2], which represents a C1 to C6 alkoxy group optionally substituted with a substituent C, or a salt thereof.
［４］
　式（２）
Figure JPOXMLDOC01-appb-C000007
　［式中、Ｒ２、Ｒ３およびＲ４は、それぞれ独立していて、
　　水素原子、
　　ハロゲン原子、
　　水酸基、
　　シアノ基、
　　ニトロ基、
　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　　Ｃ１～Ｃ６のハロアルキル基、
　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　　Ｃ２～Ｃ６のハロアルケニル基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　　Ｃ２～Ｃ６のハロアルキニル基、
　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　　Ｃ１～Ｃ６のハロアルコキシ基、
　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
　　置換基Ｄで適宜０～５置換されてもよいアリールオキシ基、
　　置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基、
　　置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、
　　Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表す。）、
　　Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、前記と同義である。）、
　　１～２個の酸素原子を含む３～６員環の基、
　　Ｒｃ－Ｌ－（ここで、Ｒｃは、Ｃ１～Ｃ６のアルキル基またはＣ１～Ｃ６のハロアルキル基を表し、Ｌは、Ｓ、ＳＯ、またはＳＯ２を表す。）、
　　ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
　　またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表し、Ｒｘ３は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。）を表し；
　Ｒ５は、
　　水素原子、
　　ハロゲン原子、
　　シアノ基、
　　ニトロ基、
　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　　Ｃ１～Ｃ６のハロアルキル基、
　　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　　Ｃ２～Ｃ６のハロアルケニル基、
　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　　Ｃ２～Ｃ６のハロアルキニル基、
　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　　Ｃ１～Ｃ６のハロアルコキシ基、
　　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
　　置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
　　Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
　　ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
　　またはＲ５１Ｃ（＝Ｏ）－（ここで、Ｒ５１は、水酸基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、またはＣ１～Ｃ６のアルコキシ基を表す。）を表し；
　Ｘは、酸素原子または硫黄原子を表し；
　Ｙは、式（ｙ－１）、または式（ｙ－２）
Figure JPOXMLDOC01-appb-C000008
を表し、
　Ｒ６は、
　　ハロゲン原子、
　　水酸基、
　　シアノ基、
　　ニトロ基、
　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
　　Ｃ１～Ｃ６のハロアルキル基、
　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
　　Ｃ２～Ｃ６のハロアルケニル基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
　　Ｃ２～Ｃ６のハロアルキニル基、
　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
　　Ｃ１～Ｃ６のハロアルコキシ基、
　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
　　置換基Ｄで適宜０～５置換されてもよいアリールオキシ基、
　　置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基、
　　置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、
　　Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、前記と同義である。）、
　　Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、前記と同義である。）、
　　１～２個の酸素原子を含む３～６員環の基、
　　Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
　　ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
　　またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２およびＲｘ３は、前記と同義である。）を表し；
　ｎは、０～３の整数（ｎが２以上の場合、２以上のＲ６はそれぞれ独立した置換基を表す。）を表し；
　そして、置換基Ａは、水酸基、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）およびＲｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）からなる群から選択される少なくとも１種であり；
　置換基Ｂは、シアノ基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種であり；
　置換基Ｃは、水酸基、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、Ｃ２～Ｃ６のアルコキシアルコキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、ＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記のＲｘ１と同義である。）および１～２個の酸素原子を含む３～６員環の基からなる群から選択される少なくとも１種であり；
　置換基Ｄは、ハロゲン原子、水酸基、シアノ基、ニトロ基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種である。］で表される化合物、またはその塩。 [4]
Equation (2)
Figure JPOXMLDOC01-appb-C000007
Wherein R2, R3 and R4 are each independently
Hydrogen atom,
Halogen atom,
Hydroxyl group,
Cyano group,
Nitro group,
A C1-C6 alkyl group optionally substituted with a substituent C,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent C,
A C2-C6 alkenyl group optionally substituted with a substituent C,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent C,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with a substituent C,
C1-C6 haloalkoxy groups,
A C3-C8 cycloalkoxy group optionally substituted with a substituent C,
A C2-C6 alkenyloxy group optionally substituted with a substituent C,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent C,
A C3-C6 haloalkynyloxy group,
An aryloxy group optionally substituted with 0 to 5 substituents D,
A heteroaryloxy group optionally substituted with 0 to 2 substituents D,
An aralkyloxy group optionally substituted with 0 to 5 substituents D,
Rx1C (＝ O)-(where Rx1 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group which may be appropriately substituted with a substituent B A group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb are each independently a hydrogen atom or a C1 which may be appropriately substituted with a substituent B) Represents an alkyl group of -C6, a haloalkyl group of C1-C6, or a cycloalkyl group of C3-C8, or Ra and Rb together with the nitrogen atom to which they are attached form an aziridinyl group, azetidinyl group, pyrrolidinyl group, Which forms a piperidinyl group, a homopiperidinyl group, or an azocanyl group)).
Rx1C (= O) O- (where Rx1 is as defined above),
A 3-6 membered ring group containing 1-2 oxygen atoms,
Rc-L-(wherein, Rc represents a haloalkyl group of alkyl or C1 ~ C6 of C1 ~ C6, L represents S, SO, or SO 2.),
RaRbN- (where Ra and Rb are as defined above),
Or Rx2C (= O) N (Rx3)-(where Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl Represents an alkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN— (where Ra and Rb have the same meanings as described above), and Rx3 represents , A hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be optionally substituted with a substituent B);
R5 is
Hydrogen atom,
Halogen atom,
Cyano group,
Nitro group,
A C1-C6 alkyl group optionally substituted with a substituent A,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent A,
A C2-C6 alkenyl group optionally substituted with a substituent A,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent A,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with a substituent A,
C1-C6 haloalkoxy groups,
A C3-C8 cycloalkoxy group optionally substituted with a substituent A,
A C2-C6 alkenyloxy group optionally substituted with a substituent A,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent A,
A C3-C6 haloalkynyloxy group,
Rc-L- (where Rc and L are as defined above),
RaRbN- (where Ra and Rb are as defined above),
Or R51C (＝ O)-(where R51 is a hydroxyl group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, or a C1 Represents an alkoxy group of -C6);
X represents an oxygen atom or a sulfur atom;
Y is the formula (y-1) or the formula (y-2)
Figure JPOXMLDOC01-appb-C000008
Represents
R6 is
Halogen atom,
Hydroxyl group,
Cyano group,
Nitro group,
A C1-C6 alkyl group optionally substituted with a substituent C,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with a substituent C,
A C2-C6 alkenyl group optionally substituted with a substituent C,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with a substituent C,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with a substituent C,
C1-C6 haloalkoxy groups,
A C3-C8 cycloalkoxy group optionally substituted with a substituent C,
A C2-C6 alkenyloxy group optionally substituted with a substituent C,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with a substituent C,
A C3-C6 haloalkynyloxy group,
An aryloxy group optionally substituted with 0 to 5 substituents D,
A heteroaryloxy group optionally substituted with 0 to 2 substituents D,
An aralkyloxy group optionally substituted with 0 to 5 substituents D,
Rx1C (= O)-(where Rx1 is as defined above),
Rx1C (= O) O- (where Rx1 is as defined above),
A 3-6 membered ring group containing 1-2 oxygen atoms,
Rc-L- (where Rc and L are as defined above),
RaRbN- (where Ra and Rb are as defined above),
Or Rx2C (= O) N (Rx3)-(where Rx2 and Rx3 are as defined above);
n represents an integer of 0 to 3 (when n is 2 or more, 2 or more R6 each represents an independent substituent);
The substituent A is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, RaRbN- (where Ra And Rb are as defined above, and Rc-L- (wherein Rc and L are as defined above), and are at least one selected from the group consisting of:
Substituent B is at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group;
Substituent C is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN -(Where Ra and Rb are as defined above), Rc-L- (where Rc and L are as defined above), RdC (= O)-(where Rd Is the same as defined above for Rx1), and is at least one member selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Substituent D is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C8 It is at least one selected from the group consisting of a C6 alkoxy group, a C1 to C6 haloalkoxy group and a C3 to C8 cycloalkoxy group. Or a salt thereof.
［５］
　［１］に記載の化合物、またはその塩を有効成分として含有する農園芸用有害生物防除剤。
［６］
　［１］に記載の化合物、またはその塩を有効成分として含有する農園芸用殺菌剤。
［７］
　［５］に記載の農園芸用有害生物防除剤を、植物、植物の種子、または植物を栽培する土壌に施用することを含む、植物病害を防除する方法。
［８］
　［６］に記載の農園芸用殺菌剤を、植物、植物の種子、または植物を栽培する土壌に施用することを含む、植物病害を防除する方法。 [5]
A pesticide for agricultural and horticultural use containing the compound according to [1] or a salt thereof as an active ingredient.
[6]
A fungicide for agricultural and horticultural use containing the compound according to [1] or a salt thereof as an active ingredient.
[7]
A method for controlling plant diseases, comprising applying the pesticidal composition for agricultural and horticultural use according to [5] to plants, plant seeds, or soil for cultivating plants.
[8]
A method for controlling plant diseases, comprising applying the fungicide for agricultural and horticultural use according to [6] to plants, plant seeds, or soil for cultivating plants.
　本発明によれば、農園芸用殺菌剤として有効である新規な化合物を提供することができる。 According to the present invention, a novel compound that is effective as an agricultural and horticultural fungicide can be provided.
　以下、本発明を実施するための形態について詳細に説明する。
　なお、特許請求の範囲および明細書中において用いられる各用語は、特に断らない限り、当該技術分野において一般的に用いられる定義によるものとする。 Hereinafter, embodiments for carrying out the present invention will be described in detail.
Each term used in the claims and the specification is defined according to a definition generally used in the technical field, unless otherwise specified.
　本明細書において、使用する略号を以下に説明する。 略 The abbreviations used in this specification are described below.
ＤＭＦ：Ｎ，Ｎ－ジメチルホルムアミド、ＴＨＦ：テトラヒドロフラン、Ｍｅ：メチル基、Ｅｔ：エチル基、Ｐｒ：プロピル基、Ｂｕ：ブチル基、Ａｃ：アセチル基、Ｐｈ：フェニル基、２－Ｔｈｉｏ：チオフェン－２－イル基、３－Ｔｈｉｏ：チオフェン－３－イル基、ｃ：シクロ、ｉ：イソ、ｓｅｃ：セカンダリ、ｔ：ターシャリ、＝：二重結合、≡：三重結合を表す。表のカラム中、Ｐｒ、Ｂｕに関しては、接頭辞がない場合は、ノルマルを意味する。 DMF: N, N-dimethylformamide, THF: tetrahydrofuran, Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Ac: acetyl group, Ph: phenyl group, 2-Thio: thiophene-2 -Yl group, 3-Thio: thiophen-3-yl group, c: cyclo, i: iso, sec: secondary, t: tertiary, =: double bond, ≡: triple bond. Regarding Pr and Bu in the columns of the table, when there is no prefix, it means normal.
　以下に、本明細書中に使用される用語の定義を説明する。 定義 The definitions of terms used in the present specification are described below.
　Ｃｘ～Ｃｙとの記載は、ｘ個からｙ個の炭素原子を有することを表す。ここで、ｘ及びｙは整数を表し、また、ｘとｙとの間に存在する全ての整数も個別に開示されているものと理解される。例えば、Ｃ１～Ｃ６は、１、２、３、４、５、または６個の炭素原子を、Ｃ１～Ｃ５は、１、２、３、４、または５個の炭素原子を、Ｃ１～Ｃ３は、１、２、または３個の炭素原子を、Ｃ２～Ｃ６は、２、３、４、５、または６個の炭素原子を、Ｃ３～Ｃ８は、３、４、５、６、７、または８個の炭素原子を、Ｃ３～Ｃ６は、３、４、５、または６個の炭素原子を、それぞれ有することを意味する。 The description Cx to Cy indicates that the compound has x to y carbon atoms. Here, x and y represent integers, and it is understood that all integers present between x and y are also individually disclosed. For example, C1-C6 has 1, 2, 3, 4, 5, or 6 carbon atoms, C1-C5 has 1, 2, 3, 4, or 5 carbon atoms, and C1-C3 has 1, 2, or 3 carbon atoms, C2-C6 has 2, 3, 4, 5, or 6 carbon atoms, and C3-C8 has 3, 4, 5, 6, 7, or Eight carbon atoms, C3-C6 means having three, four, five, or six carbon atoms, respectively.
　用語「適宜置換されてもよい」とは、置換または無置換であることを意味する。この用語を用いる際、置換基の数が明示されていないときは、置換基の数は１であることを表す。一方で、例えば、「適宜０～５置換されてもよい」と置換基の数が指定されている場合、０と５との間に存在する全ての整数も個別に開示されているものと理解される。即ち、置換基が、なし、１、２、３、４、または５個の置換基数であることを意味する。同様に、「適宜０～４置換されてもよい」では、置換基が、なし、１、２、３、または４個の置換基数を、「適宜０～３置換されてもよい」では、なし、１、２、または３個の置換基数を、「適宜０～２置換されてもよい」では、なし、１、または２個の置換基数を、それぞれ有することを意味する。 The term "optionally substituted" means substituted or unsubstituted. In using this term, when the number of substituents is not specified, it indicates that the number of substituents is 1. On the other hand, for example, when the number of substituents is specified as “may be substituted with 0 to 5 as appropriate”, it is understood that all integers present between 0 and 5 are also individually disclosed. Is done. That is, it means that the substituent has none, 1, 2, 3, 4, or 5 substituents. Similarly, in “optionally substituted with 0 to 4”, the number of substituents may be none, 1, 2, 3, or 4, and in “optionally substituted with 0 to 3”, none. The expression “may be substituted with 0 to 2 substituents” for 1, 2, or 3 substituents means none, 1 or 2 substituents, respectively.
　Ｃ１～Ｃ６のアルキル基とは、直鎖状または分岐状でよく、具体的には、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ－ブチル基、ｔ－ブチル基、ペンチル基、イソペンチル基、１－メチルブチル基、２－メチルブチル基、ネオペンチル基、１－エチルプロピル基、１，２-ジメチルプロピル基、ヘキシル基、１－メチルペンチル基、２－メチルペンチル基、３－メチルペンチル基、４－メチルペンチル基、１，１－ジメチルブチル基、２，２－ジメチルブチル基、３，３－ジメチルブチル基、１，２－ジメチルブチル基、１，３－ジメチルブチル基、２，３－ジメチルブチル基、２－エチルブチル基、１－イソプロピルプロピル基、１，１，２－トリメチルプロピル基、１，２，２－トリメチルプロピル基等が挙げられる。 The C1-C6 alkyl group may be linear or branched, and specifically, includes a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a t-butyl group. , Pentyl, isopentyl, 1-methylbutyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3 -Methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl , 2,3-dimethylbutyl, 2-ethylbutyl, 1-isopropylpropyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl And a ropyl group.
　ハロゲン原子とは、具体的には、フッ素原子、塩素原子、臭素原子、ヨウ素原子等が挙げられる。 Specific examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
　Ｃ１～Ｃ６のハロアルキル基とは、前記のＣ１～Ｃ６のアルキル基における水素原子が１個または２個以上のハロゲン原子によって任意に置換されたものを表す。２個以上のハロゲン原子で置換される場合、それらのハロゲン原子は同一または異なっていてよく、その置換数は置換基として存在することができる限り特に制限はない。Ｃ１～Ｃ６のハロアルキル基の具体例として、モノフルオロメチル基、ジフルオロメチル基、トリフルオロメチル基、モノクロロメチル基、モノブロモメチル基、モノヨードメチル基、クロロジフルオロメチル基、ブロモジフルオロメチル基、１－フルオロエチル基、２－フルオロエチル基、１，１－ジフルオロエチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、１，１，２，２－テトラフルオロエチル基、ペンタフルオロエチル基、２，２，２－トリクロロエチル基、３，３－ジフルオロプロピル基、３，３，３－トリフルオロプロピル基、ヘプタフルオロプロピル基、ヘプタフルオロイソプロピル基、２，２，２－トリフルオロ－１－（トリフルオロメチル）エチル基、ノナフルオロブチル基、ノナフルオロ－ｓｅｃ－ブチル基、３，３，４，４，５，５，５－ヘプタフルオロペンチル基、ウンデカフルオロペンチル基、トリデカフルオロヘキシル基等が挙げられる。 C1 to C6 haloalkyl group means a C1 to C6 alkyl group in which a hydrogen atom is arbitrarily substituted by one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitution is not particularly limited as long as it can be present as a substituent. Specific examples of C1 to C6 haloalkyl groups include monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, monobromomethyl, monoiodomethyl, chlorodifluoromethyl, bromodifluoromethyl, -Fluoroethyl group, 2-fluoroethyl group, 1,1-difluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group Pentafluoroethyl group, 2,2,2-trichloroethyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 2,2,2 -Trifluoro-1- (trifluoromethyl) ethyl group, nonafluorobutyl group, nonafluoro sec- butyl group, 3,3,4,4,5,5,5-heptafluoro-pentyl group, undecyl decafluoropentyl, tridecafluorohexyl group, and the like.
　Ｃ３～Ｃ８のシクロアルキル基とは、具体的には、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基等が挙げられる。 Specific examples of the C3-C8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.
　Ｃ２～Ｃ６のアルケニル基とは、１個または２個以上の二重結合を有し、直鎖状または分岐状である不飽和炭化水素基のものを表す。また、幾何異性体がある場合、Ｅ体またはＺ体のどちらか一方のみ、あるいはＥ体とＺ体との任意の割合の混合物であり、指定される炭素数の範囲であれば、特に限定されることはない。Ｃ２～Ｃ６のアルケニル基の具体例として、ビニル基、１－プロペニル基、アリル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、３－メチル－２－ブテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基、４－メチル－３－ペンテニル基、３－メチル－２－ペンテニル基等が挙げられる。 The C2-C6 alkenyl group means a linear or branched unsaturated hydrocarbon group having one or more double bonds. When there is a geometric isomer, only one of the E-form and the Z-form, or a mixture of the E-form and the Z-form in an arbitrary ratio is used, and if it is in the range of the specified number of carbon atoms, it is not particularly limited. Never. Specific examples of the C2 to C6 alkenyl groups include vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, and 3-pentenyl. Group, 4-pentenyl group, 3-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 4-methyl-3-pentenyl group, And a 3-methyl-2-pentenyl group.
　Ｃ２～Ｃ６のハロアルケニル基とは、前記のＣ２～Ｃ６のアルケニル基における水素原子が１個または２個以上のハロゲン原子によって任意に置換されたものを表す。２個以上のハロゲン原子で置換される場合、それらのハロゲン原子は同一または異なっていてよく、その置換数は置換基として存在することができる限り特に制限はない。Ｃ２～Ｃ６のハロアルケニル基の具体例として、２－フルオロビニル基、２，２－ジフルオロビニル基、２，２－ジクロロビニル基、３－フルオロアリル基、３，３－ジフルオロアリル基、３，３－ジクロロアリル基、４，４－ジフルオロ－３－ブテニル基、５，５－ジフルオロ－４－ペンテニル基、６，６－ジフルオロ－５－ヘキセニル基等が挙げられる。 The term “C2-C6 haloalkenyl group” means a C2-C6 alkenyl group in which a hydrogen atom is arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitution is not particularly limited as long as it can be present as a substituent. Specific examples of C2 to C6 haloalkenyl groups include 2-fluorovinyl, 2,2-difluorovinyl, 2,2-dichlorovinyl, 3-fluoroallyl, 3,3-difluoroallyl, Examples include a 3-dichloroallyl group, a 4,4-difluoro-3-butenyl group, a 5,5-difluoro-4-pentenyl group, and a 6,6-difluoro-5-hexenyl group.
　Ｃ２～Ｃ６のアルキニル基とは、１個または２個以上の三重結合を有し、直鎖状または分岐状である不飽和炭化水素基のものを表す。Ｃ２～Ｃ６のアルキニル基の具体例として、エチニル基、１－プロピニル基、プロパルギル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１，１－ジメチル－２－プロピニル基、１－ヘキシニル基、２－ヘキシニル基、３－ヘキシニル基、４－ヘキシニル基、５－ヘキシニル基等が挙げられる。 The C2-C6 alkynyl group means a linear or branched unsaturated hydrocarbon group having one or more triple bonds. Specific examples of the C2-C6 alkynyl group include ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, and 3-pentynyl. Group, 4-pentynyl group, 1,1-dimethyl-2-propynyl group, 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 4-hexynyl group, 5-hexynyl group and the like.
　Ｃ２～Ｃ６のハロアルキニル基とは、前記のＣ２～Ｃ６のアルキニル基における水素原子が１個または２個以上のハロゲン原子によって任意に置換されたものを表す。２個以上のハロゲン原子で置換される場合、それらのハロゲン原子は同一または異なっていてよく、その置換数は置換基として存在することができる限り特に制限はない。Ｃ２～Ｃ６のハロアルキニル基の具体例として、２－フルオロエチニル基、２－クロロエチニル基、２－ブロモエチニル基、２－ヨードエチニル基、３，３－ジフルオロ－１－プロピニル基、３－クロロ－３，３－ジフルオロ－１－プロピニル基、３－ブロモ－３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、４，４－ジフルオロ－１－ブチニル基、４，４－ジフルオロ－２－ブチニル基、４－クロロ－４，４－ジフルオロ－１－ブチニル基、４－クロロ－４，４－ジフルオロ－２－ブチニル基、４－ブロモ－４，４－ジフルオロ－１－ブチニル基、４－ブロモ－４，４－ジフルオロ－２－ブチニル基、４，４，４－トリフルオロ－１－ブチニル基、４，４，４－トリフルオロ－２－ブチニル基、５，５－ジフルオロ－３－ペンチニル基、５－クロロ－５，５－ジフルオロ－３－ペンチニル基、５－ブロモ－５，５－ジフルオロ－３－ペンチニル基、５，５，５－トリフルオロ－３－ペンチニル基、６，６－ジフルオロ－４－ヘキシニル基、６－クロロ－６，６－ジフルオロ－４－ヘキシニル基、６－ブロモ－６，６－ジフルオロ－４－ヘキシニル基、６，６，６－トリフルオロ－４－ヘキシニル基等が挙げられる。 The term “C2-C6 haloalkynyl group” means a C2-C6 alkynyl group in which a hydrogen atom is arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitution is not particularly limited as long as it can be present as a substituent. Specific examples of C2-C6 haloalkynyl groups include 2-fluoroethynyl, 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3,3-difluoro-1-propynyl, 3-chloro -3,3-difluoro-1-propynyl group, 3-bromo-3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4-difluoro-1-butynyl Group, 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro-1-butynyl group, 4-chloro-4,4-difluoro-2-butynyl group, 4-bromo-4,4 -Difluoro-1-butynyl group, 4-bromo-4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, 4,4,4-trifluoro-2-butynyl group , 5 5-difluoro-3-pentynyl group, 5-chloro-5,5-difluoro-3-pentynyl group, 5-bromo-5,5-difluoro-3-pentynyl group, 5,5,5-trifluoro-3- Pentynyl group, 6,6-difluoro-4-hexynyl group, 6-chloro-6,6-difluoro-4-hexynyl group, 6-bromo-6,6-difluoro-4-hexynyl group, 6,6,6- And a trifluoro-4-hexynyl group.
　Ｃ１～Ｃ６のアルコキシ基とは、前記のＣ１～Ｃ６のアルキル基が酸素原子を介して結合したものを表す。Ｃ１～Ｃ６のアルコキシ基の具体例として、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ブトキシ基、イソブトキシ基、ｓｅｃ－ブトキシ基、ｔ－ブトキシ基、ペンチルオキシ基、イソペンチルオキシ基、１－メチルブトキシ基、２－メチルブトキシ基、ネオペンチルオキシ基、１－エチルプロピルオキシ基、１，２-ジメチルプロピルオキシ基、ヘキシルオキシ基、１－メチルペンチルオキシ基、２－メチルペンチルオキシ基、３－メチルペンチルオキシ基、４－メチルペンチルオキシ基、１，１－ジメチルブトキシ基、２，２－ジメチルブトキシ基、３，３－ジメチルブトキシ基、１，２－ジメチルブトキシ基、１，３－ジメチルブトキシ基、２，３－ジメチルブトキシ基、２－エチルブトキシ基、１－イソプロピルプロピルオキシ基、１，１，２－トリメチルプロピルオキシ基、１，２，２－トリメチルプロピルオキシ基等が挙げられる。 C1 to C6 alkoxy group means a group in which the above C1 to C6 alkyl group is bonded via an oxygen atom. Specific examples of the C1 to C6 alkoxy groups include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutoxy, sec-butoxy, t-butoxy, pentyloxy, isopentyloxy, 1-methylbutoxy group, 2-methylbutoxy group, neopentyloxy group, 1-ethylpropyloxy group, 1,2-dimethylpropyloxy group, hexyloxy group, 1-methylpentyloxy group, 2-methylpentyloxy group , 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutoxy, 2,2-dimethylbutoxy, 3,3-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3 -Dimethylbutoxy, 2,3-dimethylbutoxy, 2-ethylbutoxy, 1-isopro A propylpropyloxy group, a 1,1,2-trimethylpropyloxy group, a 1,2,2-trimethylpropyloxy group and the like.
　Ｃ１～Ｃ６のハロアルコキシ基とは、前記のＣ１～Ｃ６のアルコキシ基における水素原子が１個または２個以上のハロゲン原子によって任意に置換されたものを表す。２個以上のハロゲン原子で置換される場合、それらのハロゲン原子は同一または異なっていてよく、その置換数は置換基として存在することができる限り特に制限はない。Ｃ１～Ｃ６のハロアルコキシ基の具体例として、ジフルオロメトキシ基、トリフルオロメトキシ基、クロロジフルオロメトキシ基、ブロモジフルオロメトキシ基、２－フルオロエトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、１，１，２，２－テトラフルオロエトキシ基、ペンタフルオロエトキシ基、２，２，２－トリクロロエトキシ基、３，３－ジフルオロプロピルオキシ基、３，３，３－トリフルオロプロピルオキシ基、ヘプタフルオロプロピルオキシ基、ヘプタフルオロイソプロピルオキシ基、２，２，２－トリフルオロ－１－（トリフルオロメチル）－エトキシ基、ノナフルオロブトキシ基、ノナフルオロ－ｓｅｃ－ブトキシ基、３，３，４，４，５，５，５－ヘプタフルオロペンチルオキシ基、ウンデカフルオロペンチルオキシ基、トリデカフルオロヘキシルオキシ基等が挙げられる。 C1 to C6 haloalkoxy group means a group in which a hydrogen atom in the above C1 to C6 alkoxy group is arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitution is not particularly limited as long as it can be present as a substituent. Specific examples of C1 to C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2 -Trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, pentafluoroethoxy, 2,2,2-trichloroethoxy, 3,3-difluoropropyloxy, 3,3,3-triethoxy Fluoropropyloxy group, heptafluoropropyloxy group, heptafluoroisopropyloxy group, 2,2,2-trifluoro-1- (trifluoromethyl) -ethoxy group, nonafluorobutoxy group, nonafluoro-sec-butoxy group, 3 , 3,4,4,5,5,5-heptafluoropentyloxy group Undecafluoro pentyloxy group, tridecafluorohexyl group, and the like.
　Ｃ３～Ｃ８のシクロアルコキシ基とは、前記のＣ３～Ｃ８のシクロアルキル基が酸素原子を介して結合したものを表す。Ｃ３～Ｃ８のシクロアルコキシ基の具体例として、シクロプロピルオキシ基、シクロブトキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基、シクロヘプチルオキシ基、シクロオクチルオキシ基等が挙げられる。 The term “C3-C8 cycloalkoxy group” refers to the above-mentioned C3-C8 cycloalkyl group bonded via an oxygen atom. Specific examples of the C3-C8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy group, and the like.
　Ｃ２～Ｃ６のアルケニルオキシ基とは、前記のＣ２～Ｃ６のアルケニル基が酸素原子を介して結合したものを表す。また、幾何異性体がある場合、Ｅ体またはＺ体のどちらか一方のみ、あるいはＥ体とＺ体との任意の割合の混合物であり、指定される炭素数の範囲であれば、特に制限されることはない。Ｃ２～Ｃ６のアルケニルオキシ基の具体例として、ビニルオキシ基、１－プロペニルオキシ基、アリルオキシ基、１－ブテニルオキシ基、２－ブテニルオキシ基、３－ブテニルオキシ基、１－ペンテニルオキシ基、２－ペンテニルオキシ基、３－ペンテニルオキシ基、４－ペンテニルオキシ基、３－メチル－２－ブテニルオキシ基、１－ヘキセニルオキシ基、２－ヘキセニルオキシ基、３－ヘキセニルオキシ基、４－ヘキセニルオキシ基、５－ヘキセニルオキシ基、３－メチル－２－ペンテニルオキシ基、４－メチル－３－ペンテニルオキシ基等が挙げられる。 The term “C2-C6 alkenyloxy group” means a group in which the above-mentioned C2-C6 alkenyl groups are bonded via an oxygen atom. In addition, when there is a geometric isomer, only one of the E-form or the Z-form, or a mixture of the E-form and the Z-form in an arbitrary ratio is used. Never. Specific examples of the C2 to C6 alkenyloxy groups include vinyloxy, 1-propenyloxy, allyloxy, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-pentenyloxy, and 2-pentenyloxy. , 3-pentenyloxy, 4-pentenyloxy, 3-methyl-2-butenyloxy, 1-hexenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-hexenyloxy Group, 3-methyl-2-pentenyloxy group, 4-methyl-3-pentenyloxy group and the like.
　Ｃ２～Ｃ６のハロアルケニルオキシ基とは、前記のＣ２～Ｃ６のアルケニルオキシ基における水素原子が１個または２個以上のハロゲン原子によって任意に置換されたものを表す。２個以上のハロゲン原子で置換される場合、それらのハロゲン原子は同一または異なっていてよく、その置換数は置換基として存在することができる限り特に制限はない。Ｃ２～Ｃ６のハロアルケニルオキシ基の具体例として、２－フルオロビニルオキシ基、２，２－ジフルオロビニルオキシ基、２，２－ジクロロビニルオキシ基、３－フルオロアリルオキシ基、３，３－ジフルオロアリルオキシ基、３，３－ジクロロアリルオキシ基、４，４－ジフルオロ－３－ブテニルオキシ基、５，５－ジフルオロ－４－ペンテニルオキシ基、６，６－ジフルオロ－５－ヘキセニルオキシ基等が挙げられる。 C2 to C6 haloalkenyloxy group means a C2 to C6 alkenyloxy group in which a hydrogen atom is arbitrarily substituted by one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitution is not particularly limited as long as it can be present as a substituent. Specific examples of C2 to C6 haloalkenyloxy groups include 2-fluorovinyloxy, 2,2-difluorovinyloxy, 2,2-dichlorovinyloxy, 3-fluoroallyloxy, and 3,3-difluoro Allyloxy group, 3,3-dichloroallyloxy group, 4,4-difluoro-3-butenyloxy group, 5,5-difluoro-4-pentenyloxy group, 6,6-difluoro-5-hexenyloxy group and the like. Can be
　Ｃ３～Ｃ６のアルキニルオキシ基とは、前記のＣ２～Ｃ６のアルキニル基のうち、Ｃ３～Ｃ６のアルキニル基が酸素原子を介して結合したものを表す。Ｃ３～Ｃ６のアルキニルオキシ基の具体例として、プロパルギルオキシ基、２－ブチニルオキシ基、３－ブチニルオキシ基、２－ペンチニルオキシ基、３－ペンチニルオキシ基、４－ペンチニルオキシ基、１，１－ジメチル－２－プロピニルオキシ基、２－ヘキシニルオキシ基、３－ヘキシニルオキシ基、４－ヘキシニルオキシ基、５－ヘキシニルオキシ基等が挙げられる。 C3-C6 alkynyloxy group means a C3-C6 alkynyl group bonded to the above-mentioned C2-C6 alkynyl group through an oxygen atom. Specific examples of the C3-C6 alkynyloxy group include propargyloxy, 2-butynyloxy, 3-butynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1,1 -Dimethyl-2-propynyloxy group, 2-hexynyloxy group, 3-hexynyloxy group, 4-hexynyloxy group, 5-hexynyloxy group and the like.
　Ｃ３～Ｃ６のハロアルキニルオキシ基とは、前記のＣ３～Ｃ６のアルキニルオキシ基における水素原子が１個または２個以上のハロゲン原子によって任意に置換されたものを表す。２個以上のハロゲン原子で置換される場合、それらのハロゲン原子は同一または異なっていてよく、その置換数は置換基として存在することができる限り特に制限はない。Ｃ３～Ｃ６のハロアルキニルオキシ基の具体例として、１，１－ジフルオロ－２－プロピニルオキシ基、４，４－ジフルオロ－２－ブチニルオキシ基、４－クロロ－４，４－ジフルオロ－２－ブチニルオキシ基、４－ブロモ－４，４－ジフルオロ－２－ブチニルオキシ基、４，４，４－トリフルオロ－２－ブチニルオキシ基、５，５－ジフルオロ－３－ペンチニルオキシ基、５－クロロ－５，５－ジフルオロ－３－ペンチニルオキシ基、５－ブロモ－５，５－ジフルオロ－３－ペンチニルオキシ基、５，５，５－トリフルオロ－３－ペンチニルオキシ基、６，６－ジフルオロ－４－ヘキシニルオキシ基、６－クロロ－６，６－ジフルオロ－４－ヘキシニルオキシ基、６－ブロモ－６，６－ジフルオロ－４－ヘキシニルオキシ基、６，６，６－トリフルオロ－４－ヘキシニルオキシ基等が挙げられる。 C3-C6 haloalkynyloxy group means a group in which a hydrogen atom in the above-mentioned C3-C6 alkynyloxy group is arbitrarily substituted with one or more halogen atoms. When substituted with two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitution is not particularly limited as long as it can be present as a substituent. Specific examples of C3-C6 haloalkynyloxy groups include 1,1-difluoro-2-propynyloxy group, 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro-2-butynyloxy group , 4-bromo-4,4-difluoro-2-butynyloxy group, 4,4,4-trifluoro-2-butynyloxy group, 5,5-difluoro-3-pentynyloxy group, 5-chloro-5,5 -Difluoro-3-pentynyloxy group, 5-bromo-5,5-difluoro-3-pentynyloxy group, 5,5,5-trifluoro-3-pentynyloxy group, 6,6-difluoro-4 -Hexynyloxy group, 6-chloro-6,6-difluoro-4-hexynyloxy group, 6-bromo-6,6-difluoro-4-hexynyloxy group, 6,6,6- Trifluoroacetic 4- hexynyloxy group.
　アリールオキシ基とは、フェニル基、ナフチル基等のアリール基が酸素原子を介して結合したものを表す。アリールオキシ基の具体例として、フェノキシ基、ナフチルオキシ基等が挙げられる。 Aryloxy group means an aryl group such as a phenyl group or a naphthyl group bonded via an oxygen atom. Specific examples of the aryloxy group include a phenoxy group and a naphthyloxy group.
　ヘテロアリールオキシ基とは、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、テトラジニル基、チエニル基、チアゾリル基、イソチアゾリル基、チアジアゾリル基、フリル基、ピロリル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基等のヘテロアリール基が酸素原子を介して結合したものを表す。ヘテロアリールオキシ基の具体例として、ピリジルオキシ基、ピリダジニルオキシ基、ピリミジニルオキシ基、ピラジニルオキシ基、トリアジニルオキシ基、テトラジニルオキシ基、チエニルオキシ基、チアゾリルオキシ基、イソチアゾリルオキシ基、チアジアゾリルオキシ基、フリルオキシ基、ピロリルオキシ基、イミダゾリルオキシ基、ピラゾリルオキシ基、オキサゾリルオキシ基、イソオキサゾリルオキシ基、トリアゾリルオキシ基、オキサジアゾリルオキシ基、チアジアゾリルオキシ基、テトラゾリルオキシ基等が挙げられる。 Heteroaryloxy groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl A heteroaryl group such as a group, isoxazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, or tetrazolyl group bonded via an oxygen atom. Specific examples of the heteroaryloxy group include a pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group, a triazinyloxy group, a tetrazinyloxy group, a thienyloxy group, a thiazolyloxy group, and an isothiazolyloxy group. Group, thiadiazolyloxy group, furyloxy group, pyrrolyloxy group, imidazolyloxy group, pyrazolyloxy group, oxazolyloxy group, isoxazolyloxy group, triazolyloxy group, oxadiazolyloxy group, thiadiazolyl group An oxy group, a tetrazolyloxy group and the like can be mentioned.
　アラルキルオキシ基とは、Ｃ１～Ｃ３のアルキル基における水素原子がフェニル基、ナフチル基等のアリール基で置換されたものであるアラルキル基が、酸素原子を介して結合したものを表す。アラルキルオキシ基の具体例として、ベンジルオキシ基、フェネチルオキシ基、フェニルプロピルオキシ基、ナフタレニルメトキシ基、ナフタレニルエトキシ基、ナフタレニルプロピルオキシ基等が挙げられる。 The term “aralkyloxy group” refers to an aralkyloxy group in which a hydrogen atom in a C1 to C3 alkyl group is substituted with an aryl group such as a phenyl group or a naphthyl group, via an oxygen atom. Specific examples of the aralkyloxy group include a benzyloxy group, a phenethyloxy group, a phenylpropyloxy group, a naphthalenylmethoxy group, a naphthalenylethoxy group, and a naphthalenylpropyloxy group.
　１～２個の酸素原子を含む３～６員環の基の具体例として、１，２－エポキシエタニル基、オキセタニル基、オキソラニル基、オキサニル基、１，３－ジオキソラニル基、１，３－ジオキサニル基、１，４－ジオキサニル基等が挙げられる。 Specific examples of the 3- to 6-membered ring group containing 1 to 2 oxygen atoms include 1,2-epoxyethanyl group, oxetanyl group, oxolanyl group, oxanyl group, 1,3-dioxolanyl group, 1,3- Examples include a dioxanyl group and a 1,4-dioxanyl group.
　Ｃ２～Ｃ６のアルコキシアルコキシ基とは、前記のＣ１～Ｃ６のアルコキシ基のうちＣ１～Ｃ５のアルコキシ基における水素原子が、１個または２個以上のＣ１～Ｃ５アルコキシ基で任意に置換されたものを表す。炭素数の総和が指定される炭素数の範囲であれば、特に限定されることはない。Ｃ２～Ｃ６のアルコキシアルコキシ基の具体例として、メトキシメトキシ基、エトキシメトキシ基、プロピルオキシメトキシ基、イソプロピルオキシメトキシ基、メトキシエトキシ基、エトキシエトキシ基、プロピルオキシエトキシ基、イソプロピルオキシエトキシ基、メトキシプロピルオキシ基、エトキシプロピルオキシ基、プロピルオキシプロピルオキシ基、イソプロピルオキシプロピルオキシ基等が挙げられる。 The C2-C6 alkoxyalkoxy group is a C1-C6 alkoxy group in which a hydrogen atom in the C1-C5 alkoxy group is optionally substituted with one or more C1-C5 alkoxy groups. Represents There is no particular limitation as long as the sum of the carbon numbers is within the specified carbon number range. Specific examples of the C2-C6 alkoxyalkoxy groups include methoxymethoxy, ethoxymethoxy, propyloxymethoxy, isopropyloxymethoxy, methoxyethoxy, ethoxyethoxy, propyloxyethoxy, isopropyloxyethoxy, and methoxypropyl. Examples thereof include an oxy group, an ethoxypropyloxy group, a propyloxypropyloxy group, and an isopropyloxypropyloxy group.
　本発明のピリドン化合物は、下記式（１）で表される化合物とその塩を包含する（以下「本発明化合物」ともいう）。 ピ リ The pyridone compound of the present invention includes a compound represented by the following formula (1) and a salt thereof (hereinafter, also referred to as “the compound of the present invention”).
Figure JPOXMLDOC01-appb-C000009
Figure JPOXMLDOC01-appb-C000009
　以下、式（１）について説明する。
　式（１）におけるＲ１は、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、Ｃ２～Ｃ６のハロアルケニルオキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、Ｃ３～Ｃ６のハロアルキニルオキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表す。 Hereinafter, equation (1) will be described.
R1 in the formula (1) is a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, or a C3 to C8 optionally substituted with a substituent A. A C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, C2-C6 Haloalkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with a substituent A, a substituent A C2-C6 alkenyloxy group optionally substituted with A; a C2-C6 haloalkenyloxy group; a C3-C6 alkynyloxy group optionally substituted with substituent A; -C6 haloalkynyloxy group, or RaRbN- (where Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, C1-C6 Represents a haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb, together with the nitrogen atom to which they are attached, represent an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group; Represents what is formed).
　中でもＲ１は、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基が好ましく、
　特にＲ１は、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基が好ましい。 Among them, R1 is a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with a substituent A, A C2-C6 alkenyl group optionally substituted with group A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent A, or a C2-C6 haloalkynyl group; Preferably
Particularly, R1 is preferably a C1 to C6 alkyl group or a C1 to C6 haloalkyl group which may be appropriately substituted with the substituent A.
　式（１）のＲ１には、水酸基、およびシアノ基が含まれる。 ＲR1 in the formula (1) includes a hydroxyl group and a cyano group.
　式（１）のＲ１における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基」のＣ１～Ｃ６のアルキル基は、前記の定義と同義であり、好ましくは、メチル基、エチル基、またはプロピル基であり、さらに好ましくは、メチル基、またはエチル基である。置換基Ａを有する場合、Ｃ１～Ｃ６のアルキル基における水素原子が、置換基Ａによって任意に置換される。 The C1 to C6 alkyl group of the “C1 to C6 alkyl group optionally substituted with the substituent A” for R1 in the formula (1) has the same meaning as described above, and is preferably a methyl group or an ethyl group. Or a propyl group, and more preferably a methyl group or an ethyl group. When it has the substituent A, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent A.
　式（１）のＲ１における「Ｃ１～Ｃ６のハロアルキル基」は、前記の定義と同義であり、好ましくは、２－フルオロエチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、３，３－ジフルオロプロピル基、または３，３，３－トリフルオロプロピル基であり、さらに好ましくは、２－フルオロエチル基、２，２－ジフルオロエチル基、または２，２，２－トリフルオロエチル基である。 The “C1 to C6 haloalkyl group” for R1 in the formula (1) is as defined above, and is preferably a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoro group. An ethyl group, a 3,3-difluoropropyl group, or a 3,3,3-trifluoropropyl group, more preferably a 2-fluoroethyl group, a 2,2-difluoroethyl group, or a 2,2,2- It is a trifluoroethyl group.
　式（１）のＲ１における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基」のＣ３～Ｃ８のシクロアルキル基は、前記の定義と同義であり、好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、またはシクロヘキシル基であり、さらに好ましくは、シクロプロピル基、またはシクロブチル基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルキル基における水素原子が、置換基Ａによって任意に置換される。 The C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with substituent A" for R1 in formula (1) has the same meaning as defined above, and is preferably a cyclopropyl group. , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group. When it has the substituent A, the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent A.
　式（１）のＲ１における「置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基」のＣ２～Ｃ６のアルケニル基は、前記の定義と同義であり、好ましくは、ビニル基、１－プロペニル基、またはアリル基であり、さらに好ましくは、ビニル基、またはアリル基である。置換基Ａを有する場合、Ｃ２～Ｃ６のアルケニル基における水素原子が、置換基Ａによって任意に置換される。 The C2 to C6 alkenyl group of the “C2 to C6 alkenyl group optionally substituted with the substituent A” for R1 in the formula (1) has the same meaning as described above, and is preferably a vinyl group, 1- It is a propenyl group or an allyl group, and more preferably a vinyl group or an allyl group. When it has the substituent A, the hydrogen atom in the alkenyl group of C2 to C6 is optionally substituted by the substituent A.
　式（１）のＲ１における「Ｃ２～Ｃ６のハロアルケニル基」は、前記の定義と同義であり、好ましくは、２－フルオロビニル基、２，２－ジフルオロビニル基、３－フルオロアリル基、または３，３－ジフルオロアリル基であり、さらに好ましくは、２－フルオロビニル基、または２，２－ジフルオロビニル基である。 The “C2-C6 haloalkenyl group” for R1 in the formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or It is a 3,3-difluoroallyl group, more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.
　式（１）のＲ１における「置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基」のＣ２～Ｃ６のアルキニル基は、前記の定義と同義であり、好ましくは、プロパルギル基、２－ブチニル基、または３－ブチニル基であり、さらに好ましくは、プロパルギル基である。置換基Ａを有する場合、Ｃ２～Ｃ６のアルキニル基における水素原子が、置換基Ａによって任意に置換される。 The C2 to C6 alkynyl group of the “C2 to C6 alkynyl group optionally substituted with the substituent A” for R1 in the formula (1) has the same meaning as defined above, and is preferably a propargyl group, It is a butynyl group or a 3-butynyl group, more preferably a propargyl group. When it has the substituent A, the hydrogen atom in the C2 to C6 alkynyl group is optionally substituted by the substituent A.
　式（１）のＲ１における「Ｃ２～Ｃ６のハロアルキニル基」は、前記の定義と同義であり、好ましくは、４，４－ジフルオロ－２－ブチニル基、４－クロロ－４，４－ジフルオロ－２－ブチニル基、４－ブロモ－４，４－ジフルオロ－２－ブチニル基、または４，４，４－トリフルオロ－２－ブチニル基であり、さらに好ましくは、４，４－ジフルオロ－２－ブチニル基、または４，４，４－トリフルオロ－２－ブチニル基である。 The “C2-C6 haloalkynyl group” for R1 in the formula (1) has the same meaning as defined above, and is preferably a 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro- A 2-butynyl group, a 4-bromo-4,4-difluoro-2-butynyl group or a 4,4,4-trifluoro-2-butynyl group, more preferably 4,4-difluoro-2-butynyl Or a 4,4,4-trifluoro-2-butynyl group.
　式（１）のＲ１における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基」のＣ１～Ｃ６のアルコキシ基は、前記の定義と同義であり、好ましくは、メトキシ基、エトキシ基、またはプロピルオキシ基であり、さらに好ましくは、メトキシ基、またはエトキシ基である。置換基Ａを有する場合、Ｃ１～Ｃ６のアルコキシ基における水素原子が、置換基Ａによって任意に置換される。 The C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with the substituent A" for R1 in the formula (1) has the same meaning as described above, and is preferably a methoxy group or an ethoxy group. Or a propyloxy group, and more preferably a methoxy group or an ethoxy group. When it has the substituent A, the hydrogen atom in the C1 to C6 alkoxy group is optionally substituted by the substituent A.
　式（１）のＲ１における「Ｃ１～Ｃ６のハロアルコキシ基」は、前記の定義と同義であり、好ましくは、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、３，３－ジフルオロプロピルオキシ基、または３，３，３－トリフルオロプロピルオキシ基であり、さらに好ましくは、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、または２，２，２－トリフルオロエトキシ基である。 The “C1 to C6 haloalkoxy group” for R1 in the formula (1) is as defined above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2 A 2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, or a 3,3,3-trifluoropropyloxy group, more preferably a difluoromethoxy group, a trifluoromethoxy group, or a 2,2-difluoroethoxy group; Or 2,2,2-trifluoroethoxy group.
　式（１）のＲ１における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基」のＣ３～Ｃ８のシクロアルコキシ基は、前記の定義と同義であり、好ましくは、シクロプロピルオキシ基、シクロブトキシ基、シクロペンチルオキシ基、またはシクロヘキシルオキシ基であり、さらに好ましくは、シクロプロピルオキシ基、またはシクロブトキシ基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルコキシ基における水素原子が、置換基Ａによって任意に置換される。 The C3-C8 cycloalkoxy group of the "C3-C8 cycloalkoxy group optionally substituted with substituent A" for R1 in formula (1) has the same meaning as defined above, and is preferably cyclopropyloxy. A cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group, and more preferably a cyclopropyloxy group or a cyclobutoxy group. When it has the substituent A, the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent A.
　式（１）のＲ１における「置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基」のＣ２～Ｃ６のアルケニルオキシ基は、前記の定義と同義であり、好ましくは、ビニルオキシ基、１－プロペニルオキシ基、またはアリルオキシ基であり、さらに好ましくは、ビニルオキシ基である。置換基Ａを有する場合、Ｃ２～Ｃ６のアルケニルオキシ基における水素原子が、置換基Ａによって任意に置換される。 The C2 to C6 alkenyloxy group of the "C2 to C6 alkenyloxy group optionally substituted with the substituent A" for R1 in the formula (1) has the same meaning as described above, and is preferably a vinyloxy group, It is a 1-propenyloxy group or an allyloxy group, and more preferably a vinyloxy group. When it has the substituent A, the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent A.
　式（１）のＲ１における「Ｃ２～Ｃ６のハロアルケニルオキシ基」とは、前記の定義と同義であり、好ましくは、２－フルオロビニルオキシ基、２，２－ジフルオロビニルオキシ基、３－フルオロアリルオキシ基、または３，３－ジフルオロアリルオキシ基であり、さらに好ましくは、２－フルオロビニルオキシ基、または２，２－ジフルオロビニルオキシ基である。 The “C2-C6 haloalkenyloxy group” in R1 of the formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 3-fluoro An allyloxy group or a 3,3-difluoroallyloxy group, more preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.
　式（１）のＲ１における「置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基」のＣ３～Ｃ６のアルキニルオキシ基は、前記の定義と同義であり、好ましくは、プロパルギルオキシ基、２－ブチニルオキシ基、または３－ブチニルオキシ基であり、さらに好ましくは、プロパルギルオキシ基である。置換基Ａを有する場合、Ｃ３～Ｃ６のアルキニルオキシ基における水素原子が、置換基Ａによって任意に置換される。 The C3 to C6 alkynyloxy group of the "C3 to C6 alkynyloxy group optionally substituted with the substituent A" for R1 in the formula (1) has the same meaning as defined above, and is preferably a propargyloxy group , A 2-butynyloxy group or a 3-butynyloxy group, and more preferably a propargyloxy group. When it has the substituent A, the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted by the substituent A.
　式（１）のＲ１における「Ｃ３～Ｃ６のハロアルキニルオキシ基」とは、前記の定義と同義であり、好ましくは、４，４－ジフルオロ－２－ブチニルオキシ基、４－クロロ－４，４－ジフルオロ－２－ブチニルオキシ基、４－ブロモ－４，４－ジフルオロ－２－ブチニルオキシ基、または４，４，４－トリフルオロ－２－ブチニルオキシ基であり、さらに好ましくは、４，４－ジフルオロ－２－ブチニルオキシ基、または４，４，４－トリフルオロ－２－ブチニルオキシ基である。 The “C3-C6 haloalkynyloxy group” in R1 of the formula (1) has the same meaning as defined above, and is preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4- A difluoro-2-butynyloxy group, a 4-bromo-4,4-difluoro-2-butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2 —Butynyloxy group or 4,4,4-trifluoro-2-butynyloxy group.
　式（１）のＲ１における「ＲａＲｂＮ－」（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）の各用語は、前記の定義と同義である。なお、「置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基」に関しては、置換基Ｂを有する場合、Ｃ１～Ｃ６のアルキル基における水素原子が、置換基Ｂによって任意に置換される。「ＲａＲｂＮ－」として、好ましくは、アミノ基、メチルアミノ基、エチルアミノ基、（メトキシメチル）アミノ基、（２－メトキシエチル）アミノ基、（シアノメチル）アミノ基、（２－シアノエチル）アミノ基、ジメチルアミノ基、エチルメチルアミノ基、ジエチルアミノ基、（メトキシメチル）メチルアミノ基、（２－メトキシエチル）メチルアミノ基、（シアノメチル）メチルアミノ基、（２－シアノエチル）メチルアミノ基、２，２－ジフルオロエチルアミノ基、２，２，２－トリフルオロエチルアミノ基、シクロプロピルアミノ基、（シクロプロピル）メチルアミノ基、ピロリジニル基、またはピペリジニル基であり、さらに好ましくは、アミノ基、ジメチルアミノ基、エチルメチルアミノ基、またはジエチルアミノ基である。 "RaRbN-" in R1 of the formula (1) (where Ra and Rb are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 Represents a haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb, together with the nitrogen atom to which they are attached, represent an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group; Each term is the same as defined above. Regarding the “C1 to C6 alkyl group optionally substituted with the substituent B”, when the compound has the substituent B, a hydrogen atom in the C1 to C6 alkyl group is optionally substituted by the substituent B. . As "RaRbN-", preferably, an amino group, a methylamino group, an ethylamino group, a (methoxymethyl) amino group, a (2-methoxyethyl) amino group, a (cyanomethyl) amino group, a (2-cyanoethyl) amino group, Dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, 2,2- A difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl) methylamino group, a pyrrolidinyl group, or a piperidinyl group, more preferably an amino group, a dimethylamino group, It is an ethylmethylamino group or a diethylamino group.
　式（１）中のＲ２、Ｒ３およびＲ４は、それぞれ独立していて、水素原子、ハロゲン原子、水酸基、シアノ基、ニトロ基、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、Ｃ２～Ｃ６のハロアルケニルオキシ基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、Ｃ３～Ｃ６のハロアルキニルオキシ基、置換基Ｄで適宜０～５置換されてもよいアリールオキシ基、置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基、置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表す。）、Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、前記と同義である。）、１～２個の酸素原子を含む３～６員環の基、Ｒｃ－Ｌ－（ここで、Ｒｃは、Ｃ１～Ｃ６のアルキル基またはＣ１～Ｃ６のハロアルキル基を表し、Ｌは、Ｓ、ＳＯ、またはＳＯ２を表す。）、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表し、Ｒｘ３は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。）を表す。 R2, R3 and R4 in the formula (1) are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent C, A C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, A C2-C6 alkynyl group optionally substituted with a substituent C, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent C, a C1-C6 haloalkoxy group, A C3-C8 cycloalkoxy group optionally substituted with a substituent C, a C2-C6 alkenyloxy group optionally substituted with a substituent C, a C2-C6 haloalkenyloxy A C3-C6 alkynyloxy group optionally substituted with a substituent C, a haloalkynyloxy group C3-C6, an aryloxy group optionally substituted with 0-5 substituents D, and a substituent D A heteroaryloxy group optionally substituted with 0 to 2; an aralkyloxy group optionally substituted with 0 to 5 substituents D; Rx1C (＝ O) — (where Rx1 is appropriately substituted with a substituent B; A C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN -(Where Ra and Rb have the same meanings as described above); Rx1C (= O) O- (where Rx1 has the same meaning as described above); and one or two oxygen atoms original 3-6 membered ring radical, Rc-L-(here including, Rc represents a haloalkyl group of alkyl or C1 ~ C6 of C1 ~ C6, L represents S, SO, or SO 2. ), RaRbN- (where Ra and Rb are as defined above), or Rx2C (= O) N (Rx3)-(where Rx2 is a hydrogen atom or a substituent B C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (Where Ra and Rb are as defined above), and Rx3 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or C A cycloalkyl group of ~ C8. ).
　中でも、Ｒ２、Ｒ３およびＲ４は、それぞれ独立していて、水素原子、ハロゲン原子、水酸基、シアノ基、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、Ｃ２～Ｃ６のハロアルケニルオキシ基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、Ｃ３～Ｃ６のハロアルキニルオキシ基、置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、またはＲｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表す。）が好ましく、
　特に、Ｒ２、Ｒ３およびＲ４は、それぞれ独立していて、水素原子、ハロゲン原子、水酸基、シアノ基、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、または置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基が好ましい。 Among them, R2, R3 and R4 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, A C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 alkynyl group optionally substituted with a substituent C, and a C1-C6 alkoxy group optionally substituted with a substituent C , A C1-C6 haloalkoxy group, a C2-C6 alkenyloxy group optionally substituted with a substituent C, a C2-C6 haloalkenyloxy group, a C3-C6 optionally substituted with a substituent C An alkynyloxy group, a C3-C6 haloalkynyloxy group, an aralkyloxy group optionally substituted with 0 to 5 substituents D, or Rx1C (（O) O— (where R 1 is a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group which may be appropriately substituted with the substituent B, A C3-C8 cycloalkoxy group or RaRbN- (where Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 Represents a haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb, together with the nitrogen atom to which they are attached, represent an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group; Represents what is formed.) Is preferable.),
In particular, R2, R3 and R4 are each independently and independently substituted with a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent C, or a substituent C. Preferred are C1 to C6 alkoxy groups which may be used.
　式（１）のＲ２には、水素原子、水酸基、シアノ基、およびニトロ基が含まれる。 ＲR2 in the formula (1) includes a hydrogen atom, a hydroxyl group, a cyano group, and a nitro group.
　式（１）のＲ２におけるハロゲン原子は、前記の定義と同義であり、好ましくはフッ素原子、塩素原子、臭素原子、またはヨウ素原子である。 ハ ロ ゲ ン The halogen atom for R2 in the formula (1) is as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
　式（１）のＲ２における「置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基」のＣ１～Ｃ６のアルキル基は、前記の定義と同義であり、好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、またはイソブチル基であり、さらに好ましくは、メチル基、またはエチル基である。置換基Ｃを有する場合、Ｃ１～Ｃ６のアルキル基における水素原子が、置換基Ｃによって任意に置換される。 The C1 to C6 alkyl group of the “C1 to C6 alkyl group optionally substituted with a substituent C” in R2 of the formula (1) has the same meaning as described above, and is preferably a methyl group or an ethyl group. Propyl group, isopropyl group, butyl group, or isobutyl group, and more preferably a methyl group or an ethyl group. When it has the substituent C, the hydrogen atom in the C1 to C6 alkyl group is optionally substituted by the substituent C.
　式（１）のＲ２における「Ｃ１～Ｃ６のハロアルキル基」は、前記の定義と同義であり、好ましくは、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、または２，２，２－トリフルオロエチル基であり、さらに好ましくは、ジフルオロメチル基、またはトリフルオロメチル基である。 The “C1 to C6 haloalkyl group” for R2 in the formula (1) is as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, or a 2,2,2 It is a 2-trifluoroethyl group, and more preferably a difluoromethyl group or a trifluoromethyl group.
　式（１）のＲ２における「置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基」のＣ３～Ｃ８のシクロアルキル基は、前記の定義と同義であり、好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、またはシクロヘキシル基であり、さらに好ましくは、シクロプロピル基、またはシクロブチル基である。置換基Ｃを有する場合、Ｃ３～Ｃ８のシクロアルキル基における水素原子が、置換基Ｃによって任意に置換される。 The C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with a substituent C" for R2 in formula (1) has the same meaning as defined above, and is preferably a cyclopropyl group. , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group. When it has the substituent C, the hydrogen atom in the C3 to C8 cycloalkyl group is optionally substituted by the substituent C.
　式（１）のＲ２における「置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基」のＣ２～Ｃ６のアルケニル基は、前記の定義と同義であり、好ましくは、ビニル基、１－プロペニル基、アリル基、１－ブテニル基、２－ブテニル基、または３－ブテニル基であり、さらに好ましくは、ビニル基、１－プロペニル基、またはアリル基である。置換基Ｃを有する場合、Ｃ２～Ｃ６のアルケニル基における水素原子が、置換基Ｃによって任意に置換される。 The C2-C6 alkenyl group of the "C2-C6 alkenyl group optionally substituted with substituent C" for R2 in formula (1) has the same meaning as defined above, and is preferably a vinyl group, 1- It is a propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group or an allyl group. When it has the substituent C, the hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent C.
　式（１）のＲ２における「Ｃ２～Ｃ６のハロアルケニル基」は、前記の定義と同義であり、好ましくは、２－フルオロビニル基、２，２－ジフルオロビニル基、２，２－ジクロロビニル基、３－フルオロアリル基、３，３－ジフルオロアリル基、または３，３－ジクロロアリル基であり、さらに好ましくは、２－フルオロビニル基、または２，２－ジフルオロビニル基である。 The “C2-C6 haloalkenyl group” for R2 in the formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group. , A 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 3,3-dichloroallyl group, and more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.
　式（１）のＲ２における「置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基」のＣ２～Ｃ６のアルキニル基は、前記の定義と同義であり、好ましくは、エチニル基、１－プロピニル基、プロパルギル基、１－ブチニル基、２－ブチニル基、または３－ブチニル基であり、さらに好ましくは、エチニル基、１－プロピニル基、またはプロパルギル基である。置換基Ｃを有する場合、Ｃ２～Ｃ６のアルキニル基における水素原子が、置換基Ｃによって任意に置換される。 The C2 to C6 alkynyl groups in the “C2 to C6 alkynyl groups optionally substituted with the substituent C” in R2 of the formula (1) are as defined above, and are preferably ethynyl group, 1- A propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, and more preferably an ethynyl group, a 1-propynyl group, or a propargyl group; When it has the substituent C, the hydrogen atom in the alkynyl group of C2 to C6 is optionally substituted by the substituent C.
　式（１）のＲ２における「Ｃ２～Ｃ６のハロアルキニル基」は、前記の定義と同義であり、好ましくは、３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、４，４－ジフルオロ－１－ブチニル基、４，４－ジフルオロ－２－ブチニル基、４，４，４－トリフルオロ－１－ブチニル基、または４，４，４－トリフルオロ－２－ブチニル基であり、さらに好ましくは、３，３－ジフルオロ－１－プロピニル基、または３，３，３－トリフルオロ－１－プロピニル基である。 The “C2-C6 haloalkynyl group” in R2 of the formula (1) has the same meaning as defined above, and is preferably a 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -Propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- It is a 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.
　式（１）のＲ２における「置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基」のＣ１～Ｃ６のアルコキシ基は、前記の定義と同義であり、好ましくは、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ブトキシ基、イソブトキシ基、またはペンチルオキシ基であり、さらに好ましくは、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ブトキシ基、またはペンチルオキシ基である。置換基Ｃを有する場合、Ｃ１～Ｃ６のアルコキシ基における水素原子が、置換基Ｃによって任意に置換される。 The C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with a substituent C" in R2 of the formula (1) has the same meaning as described above, and is preferably a methoxy group or an ethoxy group. Propyloxy group, isopropyloxy group, butoxy group, isobutoxy group, or pentyloxy group, and more preferably, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group, or pentyloxy group. When it has the substituent C, the hydrogen atom in the C1-C6 alkoxy group is optionally substituted by the substituent C.
　式（１）のＲ２における「Ｃ１～Ｃ６のハロアルコキシ基」は、前記の定義と同義であり、好ましくは、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、３，３－ジフルオロプロピルオキシ基、または３，３，３－トリフルオロプロピルオキシ基であり、さらに好ましくは、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、または２，２，２－トリフルオロエトキシ基である。 The “C1 to C6 haloalkoxy group” for R2 in the formula (1) is as defined above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2 A 2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, or a 3,3,3-trifluoropropyloxy group, more preferably a difluoromethoxy group, a trifluoromethoxy group, or a 2,2-difluoroethoxy group; Or 2,2,2-trifluoroethoxy group.
　式（１）のＲ２における「置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基」のＣ３～Ｃ８のシクロアルコキシ基は、前記の定義と同義であり、好ましくは、シクロプロピルオキシ基、シクロブトキシ基、シクロペンチルオキシ基、またはシクロヘキシルオキシ基であり、さらに好ましくは、シクロプロピルオキシ基、またはシクロブトキシ基である。置換基Ｃを有する場合、Ｃ３～Ｃ８のシクロアルコキシ基における水素原子が、置換基Ｃによって任意に置換される。 The C3-C8 cycloalkoxy group of the "C3-C8 cycloalkoxy group optionally substituted with substituent C" for R2 in formula (1) has the same meaning as defined above, and is preferably cyclopropyloxy. A cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group, and more preferably a cyclopropyloxy group or a cyclobutoxy group. When it has the substituent C, the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent C.
　式（１）のＲ２における「置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基」のＣ２～Ｃ６のアルケニルオキシ基は、前記の定義と同義であり、好ましくは、ビニルオキシ基、１－プロペニルオキシ基、アリルオキシ基、１－ブテニルオキシ基、２－ブテニルオキシ基、または３－ブテニルオキシ基であり、さらに好ましくは、ビニルオキシ基、１－プロペニルオキシ基、またはアリルオキシ基である。置換基Ｃを有する場合、Ｃ２～Ｃ６のアルケニルオキシ基における水素原子が、置換基Ｃによって任意に置換される。 The C2 to C6 alkenyloxy group of the “C2 to C6 alkenyloxy group optionally substituted with the substituent C” for R2 in the formula (1) is the same as defined above, and is preferably a vinyloxy group, A 1-propenyloxy group, an allyloxy group, a 1-butenyloxy group, a 2-butenyloxy group, or a 3-butenyloxy group is more preferable, and a vinyloxy group, a 1-propenyloxy group, or an allyloxy group is more preferable. When it has the substituent C, the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent C.
　式（１）のＲ２における「Ｃ２～Ｃ６のハロアルケニルオキシ基」は、前記の定義と同義であり、好ましくは、２－フルオロビニルオキシ基、２，２－ジフルオロビニルオキシ基、２，２－ジクロロビニルオキシ基、３－フルオロアリルオキシ基、３，３－ジフルオロアリルオキシ基、または３，３－ジクロロアリルオキシ基であり、さらに好ましくは、２－フルオロビニルオキシ基、または２，２－ジフルオロビニルオキシ基である。 The “C2-C6 haloalkenyloxy group” for R2 in the formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2- A dichlorovinyloxy group, a 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group or a 3,3-dichloroallyloxy group, more preferably a 2-fluorovinyloxy group or a 2,2-difluoro It is a vinyloxy group.
　式（１）のＲ２における「置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基」のＣ３～Ｃ６のアルキニルオキシ基は、前記の定義と同義であり、好ましくは、プロパルギルオキシ基、２－ブチニルオキシ基、または３－ブチニルオキシ基であり、さらに好ましくは、プロパルギルオキシ基、または２－ブチニルオキシ基である。置換基Ｃを有する場合、Ｃ３～Ｃ６のアルキニルオキシ基における水素原子が、置換基Ｃによって任意に置換される。 The C3-C6 alkynyloxy group of the "C3-C6 alkynyloxy group optionally substituted with the substituent C" for R2 in the formula (1) has the same meaning as defined above, and is preferably a propargyloxy group , A 2-butynyloxy group or a 3-butynyloxy group, and more preferably a propargyloxy group or a 2-butynyloxy group. When the compound has the substituent C, a hydrogen atom in the C3 to C6 alkynyloxy group is optionally substituted by the substituent C.
　式（１）のＲ２における「Ｃ３～Ｃ６のハロアルキニルオキシ基」は、前記の定義と同義であり、好ましくは、４，４－ジフルオロ－２－ブチニルオキシ基、４－クロロ－４，４－ジフルオロ－２－ブチニルオキシ基、４－ブロモ－４，４－ジフルオロ－２－ブチニルオキシ基、または４，４，４－トリフルオロ－２－ブチニルオキシ基であり、さらに好ましくは、４，４－ジフルオロ－２－ブチニルオキシ基、または４，４，４－トリフルオロ－２－ブチニルオキシ基である。 The “C3-C6 haloalkynyloxy group” in R2 of the formula (1) has the same meaning as defined above, and is preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- A butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.
　式（１）のＲ２における「置換基Ｄで適宜０～５置換されてもよいアリールオキシ基」のアリールオキシ基は、前記の定義と同義であり、好ましくは、フェノキシ基、またはナフチルオキシ基であり、さらに好ましくは、フェノキシ基である。置換基Ｄを有する場合、アリールオキシ基における水素原子が、置換基Ｄによって任意に置換される。ただし、２置換以上の置換基Ｄがある場合、それぞれは独立している。 The aryloxy group of the “aryloxy group optionally substituted with 0 to 5 substituents D” in R2 of the formula (1) has the same meaning as described above, and is preferably a phenoxy group or a naphthyloxy group. And more preferably a phenoxy group. When it has the substituent D, the hydrogen atom in the aryloxy group is optionally substituted by the substituent D. However, when there are two or more substituents D, each is independent.
　式（１）のＲ２における「置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基」のヘテロアリールオキシ基は、前記の定義と同義であり、好ましくは、ピリジルオキシ基、ピリダジニルオキシ基、ピリミジニルオキシ基、ピラジニルオキシ基、トリアジニルオキシ基、テトラジニルオキシ基、チエニルオキシ基、チアゾリルオキシ基、イソチアゾリルオキシ基、またはチアジアゾリルオキシ基であり、さらに好ましくは、ピリジルオキシ基、ピリダジニルオキシ基、ピリミジニルオキシ基、またはピラジニルオキシ基である。置換基Ｄを有する場合、ヘテロアリールオキシ基における水素原子が、置換基Ｄによって任意に置換される。ただし、２置換の置換基Ｄがある場合、それぞれは独立している。 The heteroaryloxy group of the “heteroaryloxy group optionally substituted with 0 to 2 substituent (s) D” for R 2 in formula (1) has the same meaning as defined above, and is preferably a pyridyloxy group, a pyridyl group, Dinyloxy group, pyrimidinyloxy group, pyrazinyloxy group, triazinyloxy group, tetrazinyloxy group, thienyloxy group, thiazolyloxy group, isothiazolyloxy group, or thiadiazolyloxy group, more preferably, A pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, or a pyrazinyloxy group. When the compound has the substituent D, a hydrogen atom in the heteroaryloxy group is optionally substituted by the substituent D. However, when there is a disubstituted substituent D, each is independent.
　式（１）のＲ２における「置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基」のアラルキルオキシ基は、前記の定義と同義であり、好ましくは、ベンジルオキシ基、フェネチルオキシ基、またはフェニルプロピルオキシ基であり、さらに好ましくは、ベンジルオキシ基、またはフェネチルオキシ基である。置換基Ｄを有する場合、アラルキルオキシ基における水素原子が、置換基Ｄによって任意に置換される。ただし、２置換以上の置換基Ｄがある場合、それぞれは独立している。 The aralkyloxy group of the “aralkyloxy group optionally substituted with 0 to 5 substituents D” in R2 of the formula (1) is as defined above, and is preferably a benzyloxy group, a phenethyloxy group, Or a phenylpropyloxy group, more preferably a benzyloxy group or a phenethyloxy group. When it has the substituent D, the hydrogen atom in the aralkyloxy group is optionally substituted by the substituent D. However, when there are two or more substituents D, each is independent.
　式（１）のＲ２における「Ｒｘ１Ｃ（＝Ｏ）－」（ここで、Ｒｘ１は、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表す。）の各用語は、前記の定義と同義である。なお、「置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基」に関しては、置換基Ｂを有する場合、Ｃ１～Ｃ６のアルキル基における水素原子が、置換基Ｂによって任意に置換される。Ｒｘ１として、好ましくは、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のアルコキシ基であり、さらに好ましくは、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基である。「Ｒｘ１Ｃ（＝Ｏ）－」として、好ましくは、アセチル基、メトキシアセチル基、シアノアセチル基、プロピオニル基、ジフルオロアセチル基、トリフルオロアセチル基、シクロプロパンカルボニル基、メトキシカルボニル基、エトキシカルボニル基、２，２－ジフルオロエトキシカルボニル基、２，２，２－トリフルオロエトキシカルボニル基、３，３，３－トリフルオロプロピルオキシカルボニル基、シクロプロピルオキシカルボニル基、アミノカルボニル基、メチルアミノカルボニル基、エチルアミノカルボニル基、（メトキシメチル）アミノカルボニル基、（２－メトキシエチル）アミノカルボニル基、（シアノメチル）アミノカルボニル基、（２－シアノエチル）アミノカルボニル基、ジメチルアミノカルボニル基、エチルメチルアミノカルボニル基、ジエチルアミノカルボニル基、（メトキシメチル）メチルアミノカルボニル基、（２－メトキシエチル）メチルアミノカルボニル基、（シアノメチル）メチルアミノカルボニル基、（２－シアノエチル）メチルアミノカルボニル基、２，２－ジフルオロエチルアミノカルボニル基、２，２，２－トリフルオロエチルアミノカルボニル基、シクロプロピルアミノカルボニル基、（シクロプロピル）メチルアミノカルボニル基、ピロリジニルカルボニル基、またはピペリジニルカルボニル基であり、さらに好ましくは、アセチル基、メトキシアセチル基、シアノアセチル基、プロピオニル基、ジフルオロアセチル基、トリフルオロアセチル基、メトキシカルボニル基、またはエトキシカルボニル基である。 “Rx1C (＝ O) —” in R2 of the formula (1) (where Rx1 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 A cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as described above). Are the same as defined above. Regarding the “C1 to C6 alkyl group optionally substituted with the substituent B”, when the compound has the substituent B, a hydrogen atom in the C1 to C6 alkyl group is optionally substituted by the substituent B. . Rx1 is preferably a C1-C6 alkyl group optionally substituted with a substituent B, or a C1-C6 alkoxy group, and more preferably C1-C6 optionally substituted with a substituent B. Is an alkyl group. As “Rx1C (＝ O) —”, preferably, acetyl, methoxyacetyl, cyanoacetyl, propionyl, difluoroacetyl, trifluoroacetyl, cyclopropanecarbonyl, methoxycarbonyl, ethoxycarbonyl, 2 , 2-Difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylamino Carbonyl group, (methoxymethyl) aminocarbonyl group, (2-methoxyethyl) aminocarbonyl group, (cyanomethyl) aminocarbonyl group, (2-cyanoethyl) aminocarbonyl group, dimethylaminocarbonyl group, ethylmethyl Minocarbonyl group, diethylaminocarbonyl group, (methoxymethyl) methylaminocarbonyl group, (2-methoxyethyl) methylaminocarbonyl group, (cyanomethyl) methylaminocarbonyl group, (2-cyanoethyl) methylaminocarbonyl group, 2,2- A difluoroethylaminocarbonyl group, a 2,2,2-trifluoroethylaminocarbonyl group, a cyclopropylaminocarbonyl group, a (cyclopropyl) methylaminocarbonyl group, a pyrrolidinylcarbonyl group, or a piperidinylcarbonyl group; Preferably, they are an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a methoxycarbonyl group, or an ethoxycarbonyl group.
　式（１）のＲ２における「Ｒｘ１Ｃ（＝Ｏ）Ｏ－」のＲｘ１は、前記の定義と同義である。Ｒｘ１として、好ましくは、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のアルコキシ基であり、さらに好ましくは、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基である。「Ｒｘ１Ｃ（＝Ｏ）Ｏ－」として、好ましくは、アセチルオキシ基、メトキシアセチルオキシ基、シアノアセチルオキシ基、プロピオニルオキシ基、ジフルオロアセチルオキシ基、トリフルオロアセチルオキシ基、シクロプロパンカルボニルオキシ基、メトキシカルボニルオキシ基、エトキシカルボニルオキシ基、２，２－ジフルオロエトキシカルボニルオキシ基、２，２，２－トリフルオロエトキシカルボニルオキシ基、３，３，３－トリフルオロプロピルオキシカルボニルオキシ基、シクロプロピルオキシカルボニルオキシ基、アミノカルボニルオキシ基、メチルアミノカルボニルオキシ基、エチルアミノカルボニルオキシ基、（メトキシメチル）アミノカルボニルオキシ基、（２－メトキシエチル）アミノカルボニルオキシ基、（シアノメチル）アミノカルボニルオキシ基、（２－シアノエチル）アミノカルボニルオキシ基、ジメチルアミノカルボニルオキシ基、エチルメチルアミノカルボニルオキシ基、ジエチルアミノカルボニルオキシ基、（メトキシメチル）メチルアミノカルボニルオキシ基、（２－メトキシエチル）メチルアミノカルボニルオキシ基、（シアノメチル）メチルアミノカルボニルオキシ基、（２－シアノエチル）メチルアミノカルボニルオキシ基、２，２－ジフルオロエチルアミノカルボニルオキシ基、２，２，２－トリフルオロエチルアミノカルボニルオキシ基、シクロプロピルアミノカルボニルオキシ基、（シクロプロピル）メチルアミノカルボニルオキシ基、ピロリジニルカルボニルオキシ基、またはピペリジニルカルボニルオキシ基であり、さらに好ましくは、アセチルオキシ基、メトキシアセチルオキシ基、シアノアセチルオキシ基、またはプロピオニルオキシ基である。 ＲRx1 of “Rx1C (＝ O) O−” in R2 of the formula (1) is as defined above. Rx1 is preferably a C1-C6 alkyl group optionally substituted with a substituent B, or a C1-C6 alkoxy group, and more preferably C1-C6 optionally substituted with a substituent B. Is an alkyl group. As “Rx1C (＝ O) O—”, preferably, acetyloxy, methoxyacetyloxy, cyanoacetyloxy, propionyloxy, difluoroacetyloxy, trifluoroacetyloxy, cyclopropanecarbonyloxy, methoxy Carbonyloxy group, ethoxycarbonyloxy group, 2,2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, 3,3,3-trifluoropropyloxycarbonyloxy group, cyclopropyloxycarbonyl Oxy group, aminocarbonyloxy group, methylaminocarbonyloxy group, ethylaminocarbonyloxy group, (methoxymethyl) aminocarbonyloxy group, (2-methoxyethyl) aminocarbonyloxy group, Methyl) aminocarbonyloxy group, (2-cyanoethyl) aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethylmethylaminocarbonyloxy group, diethylaminocarbonyloxy group, (methoxymethyl) methylaminocarbonyloxy group, (2-methoxyethyl ) Methylaminocarbonyloxy group, (cyanomethyl) methylaminocarbonyloxy group, (2-cyanoethyl) methylaminocarbonyloxy group, 2,2-difluoroethylaminocarbonyloxy group, 2,2,2-trifluoroethylaminocarbonyloxy A cyclopropylaminocarbonyloxy group, a (cyclopropyl) methylaminocarbonyloxy group, a pyrrolidinylcarbonyloxy group, or a piperidinylcarbonyloxy group; Preferably, the acetyloxy group, methoxyacetyl group, a cyano acetyloxy group or propionyloxy group.
　式（１）のＲ２における「１～２個の酸素原子を含む３～６員環の基」は、前記の定義と同義であり、好ましくは、オキソラニル基、オキサニル基、１，３－ジオキソラニル基、または１，３－ジオキサニル基であり、さらに好ましくは、１，３－ジオキソラニル基、または１，３－ジオキサニル基である。 The “3- to 6-membered ring group containing 1 or 2 oxygen atoms” in R 2 of the formula (1) is as defined above, and is preferably an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group. Or a 1,3-dioxanyl group, and more preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.
　式（１）のＲ２における「Ｒｃ－Ｌ－」（ここで、Ｒｃは、Ｃ１～Ｃ６のアルキル基またはＣ１～Ｃ６のハロアルキル基を表し、Ｌは、Ｓ、ＳＯ、またはＳＯ２を表す。）の各用語は、前記の定義と同義である。「Ｒｃ－Ｌ－」として、好ましくは、メチルチオ基、メタンスルフィニル基、メタンスルホニル基、トリフルオロメチルチオ基、トリフルオロメタンスルフィニル基、またはトリフルオロメタンスルホニル基であり、さらに好ましくは、メチルチオ基、メタンスルフィニル基、またはメタンスルホニル基である。 "Rc-L -" in R2 of formula (1) (wherein, Rc represents a haloalkyl group of alkyl or C1 ~ C6 of C1 ~ C6, L represents S, SO, or SO 2.) Are the same as defined above. "Rc-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group Or a methanesulfonyl group.
　式（１）のＲ２における「ＲａＲｂＮ－」のＲａおよびＲｂは、前記と同義である。「ＲａＲｂＮ－」として、好ましくは、アミノ基、メチルアミノ基、エチルアミノ基、（メトキシメチル）アミノ基、（２－メトキシエチル）アミノ基、（シアノメチル）アミノ基、（２－シアノエチル）アミノ基、ジメチルアミノ基、エチルメチルアミノ基、ジエチルアミノ基、（メトキシメチル）メチルアミノ基、（２－メトキシエチル）メチルアミノ基、（シアノメチル）メチルアミノ基、（２－シアノエチル）メチルアミノ基、２，２－ジフルオロエチルアミノ基、２，２，２－トリフルオロエチルアミノ基、シクロプロピルアミノ基、（シクロプロピル）メチルアミノ基、ピロリジニル基、またはピペリジニル基であり、さらに好ましくは、アミノ基、メチルアミノ基、エチルアミノ基、ジメチルアミノ基、エチルメチルアミノ基、またはジエチルアミノ基である。 ＲRa and Rb of "RaRbN-" in R2 of the formula (1) are as defined above. As "RaRbN-", preferably, an amino group, a methylamino group, an ethylamino group, a (methoxymethyl) amino group, a (2-methoxyethyl) amino group, a (cyanomethyl) amino group, a (2-cyanoethyl) amino group, Dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, 2,2- A difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl) methylamino group, a pyrrolidinyl group, or a piperidinyl group, more preferably an amino group, a methylamino group, Ethylamino group, dimethylamino group, ethylmethylamino group Or a diethylamino group.
　式（１）のＲ２における「Ｒｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－」（ここで、Ｒｘ２は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表し、Ｒｘ３は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。）の各用語は、前記の定義と同義である。なお、Ｒｘ２およびＲｘ３における「置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基」に関しては、置換基Ｂを有する場合、Ｃ１～Ｃ６のアルキル基における水素原子が、置換基Ｂによって任意に置換される。Ｒｘ２として、好ましくは、水素原子、メチル基、メトキシメチル基、シアノメチル基、エチル基、ジフルオロメチル基、トリフルオロメチル基、シクロプロピル基、メトキシ基、エトキシ基、２，２－ジフルオロエトキシ、２，２，２－トリフルオロエトキシ基、シクロプロピルオキシ基、アミノ基、メチルアミノ基、エチルアミノ基、（メトキシメチル）アミノ基、（２－メトキシエチル）アミノ基、（シアノメチル）アミノ基、（２－シアノエチル）アミノ基、ジメチルアミノ基、エチルメチルアミノ基、ジエチルアミノ基、（メトキシメチル）メチルアミノ基、（２－メトキシエチル）メチルアミノ基、（シアノメチル）メチルアミノ基、（２－シアノエチル）メチルアミノ基、２，２－ジフルオロエチルアミノ基、２，２，２－トリフルオロエチルアミノ基、シクロプロピルアミノ基、（シクロプロピル）メチルアミノ基、ピロリジニル基、またはピペリジニル基であり、さらに好ましくは、水素原子、メチル基、メトキシメチル基、シアノメチル基、ジフルオロメチル基、トリフルオロメチル基、メトキシ基、エトキシ基、アミノ基、ジメチルアミノ基、エチルメチルアミノ基、またはジエチルアミノ基である。また、Ｒｘ３として、好ましくは、水素原子、メチル基、メトキシメチル基、エトキシメチル基、シアノメチル基、エチル基、２－メトキシエチル基、２－エトキシエチル基、２－シアノエチル基、プロピル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、またはシクロプロピル基であり、さらに好ましくは、水素原子、メチル基、メトキシメチル基、シアノメチル基、エチル基、２－メトキシエチル基、２，２－ジフルオロエチル基、または２，２，２－トリフルオロエチル基である。 “Rx2C (＝ O) N (Rx3) —” in R2 of the formula (1) (where Rx2 is a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 A haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb are as defined above) Rx3 represents a hydrogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group optionally substituted with a substituent B). The terms are as defined above. Regarding the “C1 to C6 alkyl group optionally substituted with a substituent B” in Rx2 and Rx3, when the compound has a substituent B, a hydrogen atom in the C1 to C6 alkyl group may be optionally selected depending on the substituent B. Is replaced by Rx2 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a difluoromethyl group, a trifluoromethyl group, a cyclopropyl group, a methoxy group, an ethoxy group, a 2,2-difluoroethoxy, 2,2-trifluoroethoxy, cyclopropyloxy, amino, methylamino, ethylamino, (methoxymethyl) amino, (2-methoxyethyl) amino, (cyanomethyl) amino, (2- (Cyanoethyl) amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group 2,2-difluoroethylamino group, 2,2,2-to A fluoroethylamino group, a cyclopropylamino group, a (cyclopropyl) methylamino group, a pyrrolidinyl group, or a piperidinyl group, more preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, a difluoromethyl group, a trifluoromethyl group; A methyl group, a methoxy group, an ethoxy group, an amino group, a dimethylamino group, an ethylmethylamino group, or a diethylamino group. Rx3 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-cyanoethyl group, a propyl group, A 2-difluoroethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropyl group, more preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, It is a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.
　式（１）中のＲ３は、前記したＲ２と同義である。 ＲR3 in the formula (1) has the same meaning as R2 described above.
　式（１）中のＲ４は、前記したＲ２と同義である。 ＲR4 in the formula (1) has the same meaning as R2 described above.
　式（１）中のＲ２、Ｒ３およびＲ４は、それぞれ独立していて、同一もしくは異なっていてよく、特に制限されることはない。 ＲR2, R3 and R4 in the formula (1) are each independent and may be the same or different and are not particularly limited.
　式（１）におけるＲ５は、水素原子、ハロゲン原子、シアノ基、ニトロ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、Ｃ２～Ｃ６のハロアルケニルオキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、Ｃ３～Ｃ６のハロアルキニルオキシ基、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、またはＲ５１Ｃ（＝Ｏ）－（ここで、Ｒ５１は、水酸基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、またはＣ１～Ｃ６のアルコキシ基を表す。）を表す。 R5 in the formula (1) is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a substituent A optionally substituted. C3-C8 cycloalkyl group which may be optionally substituted, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 haloalkenyl group, C2-C6 optionally substituted with substituent A An alkynyl group, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent A, a C1-C6 haloalkoxy group, and a C3-C8 optionally substituted with a substituent A A C2-C6 alkenyloxy group optionally substituted with a substituent A, a C3-C6 haloalkenyloxy group optionally substituted with a substituent A, and a C3- 6, an alkynyloxy group of 6, a haloalkynyloxy group of C3-C6, Rc-L- (where Rc and L are as defined above), RaRbN- (where Ra and Rb are as defined above) Or R51C (＝ O) — (where R51 is a hydroxyl group, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group). An alkyl group or a C1 to C6 alkoxy group).
　中でもＲ５は、水素原子、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、またはＲ５１Ｃ（＝Ｏ）－（ここで、Ｒ５１は、水酸基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、またはＣ１～Ｃ６のアルコキシ基を表す。）が好ましく、
　特にＲ５は、水素原子、ハロゲン原子、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、または置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基が好ましい。 Among them, R5 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent A. A C2-C6 alkynyl group optionally substituted with a substituent A, a C1-C6 alkoxy group optionally substituted with a substituent A, a C2-C6 alkenyl optionally substituted with a substituent A An oxy group, a C3-C6 alkynyloxy group optionally substituted with a substituent A, or R51C (= O)-(where R51 is a hydroxyl group or a C1-C6 optionally substituted with a substituent B) Represents a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, or a C1-C6 alkoxy group.)
In particular, R5 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a C2-C6 alkynyl optionally substituted with a substituent A. Groups are preferred.
　式（１）のＲ５には、水素原子、シアノ基、およびニトロ基が含まれる。 ＲR5 in the formula (1) includes a hydrogen atom, a cyano group, and a nitro group.
　式（１）のＲ５におけるハロゲン原子は、前記の定義と同義であり、好ましくは、フッ素原子、塩素原子、臭素原子、またはヨウ素原子である。 ハ ロ ゲ ン The halogen atom for R5 in the formula (1) has the same meaning as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
　式（１）のＲ５における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基」のＣ１～Ｃ６のアルキル基は、前記の定義と同義であり、好ましくは、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、またはイソブチル基であり、さらに好ましくは、メチル基、またはエチル基である。置換基Ａを有する場合、Ｃ１～Ｃ６のアルキル基における水素原子が、置換基Ａによって任意に置換される。 The C1 to C6 alkyl group of the “C1 to C6 alkyl group optionally substituted with the substituent A” for R5 in the formula (1) is the same as defined above, and is preferably a methyl group or an ethyl group. Propyl group, isopropyl group, butyl group, or isobutyl group, and more preferably a methyl group or an ethyl group. When it has the substituent A, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent A.
　式（１）のＲ５における「Ｃ１～Ｃ６のハロアルキル基」は、前記の定義と同義であり、好ましくは、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、３，３－ジフルオロプロピル基、または３，３，３－トリフルオロプロピル基であり、さらに好ましくは、ジフルオロメチル基、またはトリフルオロメチル基である。 The “C1 to C6 haloalkyl group” for R5 in the formula (1) is as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2 A trifluoroethyl group, a 3,3-difluoropropyl group or a 3,3,3-trifluoropropyl group, more preferably a difluoromethyl group or a trifluoromethyl group.
　式（１）のＲ５における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基」のＣ３～Ｃ８のシクロアルキル基は、前記の定義と同義であり、好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、またはシクロヘキシル基であり、さらに好ましくは、シクロプロピル基、またはシクロブチル基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルキル基における水素原子が、置換基Ａによって任意に置換される。 The C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with substituent A" for R5 in the formula (1) is as defined above, and is preferably a cyclopropyl group. , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group. When it has the substituent A, the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent A.
　式（１）のＲ５における「置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基」のＣ２～Ｃ６のアルケニル基は、前記の定義と同義であり、好ましくは、ビニル基、１－プロペニル基、アリル基、１－ブテニル基、２－ブテニル基、または３－ブテニル基であり、さらに好ましくは、ビニル基、１－プロペニル基、またはアリル基である。置換基Ａを有する場合、Ｃ２～Ｃ６のアルケニル基における水素原子が、置換基Ａによって任意に置換される。 The C2 to C6 alkenyl group of the “C2 to C6 alkenyl group optionally substituted with the substituent A” in R5 of the formula (1) has the same meaning as described above, and is preferably a vinyl group, 1- It is a propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group or an allyl group. When it has the substituent A, the hydrogen atom in the alkenyl group of C2 to C6 is optionally substituted by the substituent A.
　式（１）のＲ５における「Ｃ２～Ｃ６のハロアルケニル基」は、前記の定義と同義であり、好ましくは、２－フルオロビニル基、２，２－ジフルオロビニル基、２，２－ジクロロビニル基、３－フルオロアリル基、３，３－ジフルオロアリル基、または３，３－ジクロロアリル基であり、さらに好ましくは、２－フルオロビニル基、または２，２－ジフルオロビニル基である。 The “C2-C6 haloalkenyl group” for R5 in the formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group. , A 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 3,3-dichloroallyl group, and more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.
　式（１）のＲ５における「置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基」のＣ２～Ｃ６のアルキニル基は、前記の定義と同義であり、好ましくは、エチニル基、１－プロピニル基、プロパルギル基、１－ブチニル基、２－ブチニル基、または３－ブチニル基であり、さらに好ましくは、エチニル基、１－プロピニル基、またはプロパルギル基である。置換基Ａを有する場合、Ｃ２～Ｃ６のアルキニル基における水素原子が、置換基Ａによって任意に置換される。 The C2 to C6 alkynyl group of the “C2 to C6 alkynyl group optionally substituted with the substituent A” for R5 in the formula (1) has the same meaning as described above, and is preferably an ethynyl group, 1- A propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, and more preferably an ethynyl group, a 1-propynyl group, or a propargyl group; When it has the substituent A, the hydrogen atom in the C2 to C6 alkynyl group is optionally substituted by the substituent A.
　式（１）のＲ５における「Ｃ２～Ｃ６のハロアルキニル基」は、前記の定義と同義であり、好ましくは、３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、４，４－ジフルオロ－１－ブチニル基、４，４－ジフルオロ－２－ブチニル基、４，４，４－トリフルオロ－１－ブチニル基、または４，４，４－トリフルオロ－２－ブチニル基であり、さらに好ましくは、３，３－ジフルオロ－１－プロピニル基、または３，３，３－トリフルオロ－１－プロピニル基である。 The “C2-C6 haloalkynyl group” in R5 of the formula (1) is as defined above, and is preferably a 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -Propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- It is a 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.
　式（１）のＲ５における「置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基」のＣ１～Ｃ６のアルコキシ基は、前記の定義と同義であり、好ましくは、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ブトキシ基、またはイソブトキシ基であり、さらに好ましくは、メトキシ基、またはエトキシ基である。置換基Ａを有する場合、Ｃ１～Ｃ６のアルコキシ基における水素原子が、置換基Ａによって任意に置換される。 The C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with the substituent A" in R5 of the formula (1) has the same meaning as described above, and is preferably a methoxy group or an ethoxy group. Propyloxy group, isopropyloxy group, butoxy group, or isobutoxy group, and more preferably methoxy group or ethoxy group. When it has the substituent A, the hydrogen atom in the C1 to C6 alkoxy group is optionally substituted by the substituent A.
　式（１）のＲ５における「Ｃ１～Ｃ６のハロアルコキシ基」は、前記の定義と同義であり、好ましくは、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、３，３－ジフルオロプロピルオキシ基、または３，３，３－トリフルオロプロピルオキシ基であり、さらに好ましくは、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、または２，２，２－トリフルオロエトキシ基である。 The “C1 to C6 haloalkoxy group” for R5 in the formula (1) is as defined above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2 A 2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, or a 3,3,3-trifluoropropyloxy group, more preferably a difluoromethoxy group, a trifluoromethoxy group, or a 2,2-difluoroethoxy group; Or 2,2,2-trifluoroethoxy group.
　式（１）のＲ５における「置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基」のＣ３～Ｃ８のシクロアルコキシ基は、前記の定義と同義であり、好ましくは、シクロプロピルオキシ基、シクロブトキシ基、シクロペンチルオキシ基、またはシクロヘキシルオキシ基であり、さらに好ましくは、シクロプロピルオキシ基、またはシクロブトキシ基である。置換基Ａを有する場合、Ｃ３～Ｃ８のシクロアルコキシ基における水素原子が、置換基Ａによって任意に置換される。 The C3-C8 cycloalkoxy group of the "C3-C8 cycloalkoxy group optionally substituted with substituent A" for R5 in formula (1) has the same meaning as defined above, and is preferably cyclopropyloxy. A cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group, and more preferably a cyclopropyloxy group or a cyclobutoxy group. When it has the substituent A, the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent A.
　式（１）のＲ５における「置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基」のＣ２～Ｃ６のアルケニルオキシ基は、前記の定義と同義であり、好ましくは、ビニルオキシ基、１－プロペニルオキシ基、アリルオキシ基、１－ブテニルオキシ基、２－ブテニルオキシ基、または３－ブテニルオキシ基であり、さらに好ましくは、ビニルオキシ基、１－プロペニルオキシ基、またはアリルオキシ基である。置換基Ａを有する場合、Ｃ２～Ｃ６のアルケニルオキシ基における水素原子が、置換基Ａによって任意に置換される。 The C2-C6 alkenyloxy group of the “C2-C6 alkenyloxy group optionally substituted with the substituent A” for R5 in the formula (1) has the same meaning as defined above, and is preferably a vinyloxy group, A 1-propenyloxy group, an allyloxy group, a 1-butenyloxy group, a 2-butenyloxy group, or a 3-butenyloxy group is more preferable, and a vinyloxy group, a 1-propenyloxy group, or an allyloxy group is more preferable. When it has the substituent A, the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent A.
　式（１）のＲ５における「Ｃ２～Ｃ６のハロアルケニルオキシ基」は、前記の定義と同義であり、２－フルオロビニルオキシ基、２，２－ジフルオロビニルオキシ基、２，２－ジクロロビニルオキシ基、３－フルオロアリルオキシ基、３，３－ジフルオロアリルオキシ基、または３，３－ジクロロアリルオキシ基であり、さらに好ましくは、２－フルオロビニルオキシ基、または２，２－ジフルオロビニルオキシ基である。 The “C2 to C6 haloalkenyloxy group” for R5 in the formula (1) is as defined above, and is a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2-dichlorovinyloxy group. A 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group, or a 3,3-dichloroallyloxy group, more preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group It is.
　式（１）のＲ５における「置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基」のＣ３～Ｃ６のアルキニルオキシ基は、前記の定義と同義であり、好ましくは、プロパルギルオキシ基、２－ブチニルオキシ基、または３－ブチニルオキシ基であり、さらに好ましくは、プロパルギルオキシ基である。置換基Ａを有する場合、Ｃ３～Ｃ６のアルキニルオキシ基における水素原子が、置換基Ａによって任意に置換される。 The C3-C6 alkynyloxy group of the "C3-C6 alkynyloxy group optionally substituted with the substituent A" for R5 in the formula (1) has the same meaning as defined above, and is preferably a propargyloxy group , A 2-butynyloxy group or a 3-butynyloxy group, and more preferably a propargyloxy group. When it has the substituent A, the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted by the substituent A.
　式（１）のＲ５における「Ｃ３～Ｃ６のハロアルキニルオキシ基」は、前記の定義と同義であり、好ましくは、４，４－ジフルオロ－２－ブチニルオキシ基、４－クロロ－４，４－ジフルオロ－２－ブチニルオキシ基、４－ブロモ－４，４－ジフルオロ－２－ブチニルオキシ基、または４，４，４－トリフルオロ－２－ブチニルオキシ基であり、さらに好ましくは、４，４－ジフルオロ－２－ブチニルオキシ基、または４，４，４－トリフルオロ－２－ブチニルオキシ基である。 The “C3-C6 haloalkynyloxy group” for R5 in the formula (1) is as defined above, and preferably is a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro group. -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- A butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.
　式（１）のＲ５における「Ｒｃ－Ｌ－」のＲｃおよびＬは、前記と同義である。「Ｒｃ－Ｌ－」として、好ましくは、メチルチオ基、メタンスルフィニル基、メタンスルホニル基、トリフルオロメチルチオ基、トリフルオロメタンスルフィニル基、またはトリフルオロメタンスルホニル基であり、さらに好ましくは、メチルチオ基、メタンスルフィニル基、またはメタンスルホニル基である。 ＲRc and L of "Rc-L-" in R5 of the formula (1) are as defined above. "Rc-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group Or a methanesulfonyl group.
　式（１）のＲ５における「ＲａＲｂＮ－」のＲａおよびＲｂは、前記と同義である。「ＲａＲｂＮ－」として、好ましくは、アミノ基、メチルアミノ基、エチルアミノ基、（メトキシメチル）アミノ基、（２－メトキシエチル）アミノ基、（シアノメチル）アミノ基、（２－シアノエチル）アミノ基、ジメチルアミノ基、エチルメチルアミノ基、ジエチルアミノ基、（メトキシメチル）メチルアミノ基、（２－メトキシエチル）メチルアミノ基、（シアノメチル）メチルアミノ基、（２－シアノエチル）メチルアミノ基、２，２－ジフルオロエチルアミノ基、２，２，２－トリフルオロエチルアミノ基、シクロプロピルアミノ基、（シクロプロピル）メチルアミノ基、ピロリジニル基、またはピペリジニル基であり、さらに好ましくは、ジメチルアミノ基、エチルメチルアミノ基、またはジエチルアミノ基である。 ＲRa and Rb of "RaRbN-" in R5 of the formula (1) are as defined above. As "RaRbN-", preferably, an amino group, a methylamino group, an ethylamino group, a (methoxymethyl) amino group, a (2-methoxyethyl) amino group, a (cyanomethyl) amino group, a (2-cyanoethyl) amino group, Dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, 2,2- A difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl) methylamino group, a pyrrolidinyl group, or a piperidinyl group, and more preferably a dimethylamino group or an ethylmethylamino group; Or a diethylamino group.
　式（１）のＲ５における「Ｒ５１Ｃ（＝Ｏ）－」（ここで、Ｒ５１は、水酸基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、またはＣ１～Ｃ６のアルコキシ基を表す。）の各用語は、前記の定義と同義である。なお、「置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基」に関しては、置換基Ｂを有する場合、Ｃ１～Ｃ６のアルキル基における水素原子が、置換基Ｂによって任意に置換される。Ｒ５１として、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基が好ましい。「Ｒ５１Ｃ（＝Ｏ）－」として、好ましくは、ヒドロキシカルボニル基、アセチル基、メトキシアセチル基、シアノアセチル基、プロピオニル基、ジフルオロアセチル基、トリフルオロアセチル基、シクロプロパンカルボニル基、メトキシカルボニル基、またはエトキシカルボニル基であり、さらに好ましくは、アセチル基、メトキシアセチル基、シアノアセチル基、またはプロピオニル基である。 “R51C (＝ O) —” in R5 of the formula (1) (where R51 is a hydroxyl group, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C3 to Each of which represents a cycloalkyl group of C8 or an alkoxy group of C1 to C6) has the same meaning as defined above. Regarding the “C1 to C6 alkyl group optionally substituted with the substituent B”, when the compound has the substituent B, a hydrogen atom in the C1 to C6 alkyl group is optionally substituted by the substituent B. . R51 is preferably a C1 to C6 alkyl group optionally substituted with a substituent B. As "R51C (= O)-", preferably, a hydroxycarbonyl group, an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, or An ethoxycarbonyl group, more preferably an acetyl group, a methoxyacetyl group, a cyanoacetyl group, or a propionyl group.
　式（１）のＸは、酸素原子、または硫黄原子を表す。好ましいＸは、酸素原子である。 X in the formula (1) represents an oxygen atom or a sulfur atom. Preferred X is an oxygen atom.
　Ｙは、式（ｙ－１）、または式（ｙ－２）
Figure JPOXMLDOC01-appb-C000010
を表す。 Y is the formula (y-1) or the formula (y-2)
Figure JPOXMLDOC01-appb-C000010
Represents
　Ｒ６は、ハロゲン原子、水酸基、シアノ基、ニトロ基、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、Ｃ２～Ｃ６のハロアルケニルオキシ基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、Ｃ３～Ｃ６のハロアルキニルオキシ基、置換基Ｄで適宜０～５置換されてもよいアリールオキシ基、置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基、置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、前記と同義である。）、Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、前記と同義である。）、１～２個の酸素原子を含む３～６員環の基、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２およびＲｘ３は、前記と同義である。）を表す。 R6 is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, or a C3 to C3 optionally substituted with a substituent C. A C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent C; C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent C, substitution A C2-C6 alkenyloxy group optionally substituted with a group C, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with a substituent C; C, a C3-C6 haloalkynyloxy group, an aryloxy group optionally substituted with 0 to 5 substituents D, a heteroaryloxy group optionally substituted with 0 to 2 substituents D, a substituent D An aralkyloxy group optionally substituted with 0 to 5; Rx1C (＝ O) — (where Rx1 has the same meaning as described above); and Rx1C (＝ O) O— (where Rx1 is A 3- to 6-membered ring group containing 1 or 2 oxygen atoms, Rc-L- (where Rc and L are as defined above), RaRbN- (wherein , Ra and Rb are as defined above, or Rx2C (= O) N (Rx3)-(where Rx2 and Rx3 are as defined above).
　中でもＲ６は、ハロゲン原子、水酸基、シアノ基、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、前記と同義である。）、Ｒｃ－Ｌ－（ここで、Ｒｃは、Ｃ１～Ｃ６のアルキル基またはＣ１～Ｃ６のハロアルキル基を表し、Ｌは、Ｓ、ＳＯ、またはＳＯ２を表す。）、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）が好ましく、
　特にＲ６は、ハロゲン原子、シアノ基、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、または置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基が好ましい。 Among them, R6 is a halogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, or a C2 to C6 optionally substituted with a substituent C. An alkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent C, a C1-C6 alkoxy group optionally substituted with a substituent C, a haloalkoxy group C1-C6, optionally with a substituent C An optionally substituted C2 to C6 alkenyloxy group, an optionally substituted C3 to C6 alkynyloxy group with a substituent C, Rx1C (） O) — (where Rx1 is as defined above). ), Rc-L- (wherein, Rc represents a C1 ~ C6 alkyl group or a C1 ~ C6 haloalkyl group, L is, S, SO or an SO 2,.), or RaRbN- (here , Ra and Rb are as defined above).
In particular, R6 is a halogen atom, a cyano group, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, or a C1-C6 alkoxy optionally substituted with a substituent C. Groups are preferred.
　式（１）のＲ６におけるハロゲン原子は、前記の定義と同義であり、好ましくはフッ素原子、塩素原子、臭素原子、またはヨウ素原子である。 ハ ロ ゲ ン The halogen atom in R6 of the formula (1) has the same meaning as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
　式（１）のＲ６には、水酸基、シアノ基、およびニトロ基が含まれる。 ＲR6 in the formula (1) includes a hydroxyl group, a cyano group, and a nitro group.
　式（１）のＲ６における「置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基」のＣ１～Ｃ６のアルキル基は、前記の定義と同義であり、好ましくは、メチル基、エチル基、またはプロピル基であり、さらに好ましくは、メチル基、またはエチル基である。置換基Ｃを有する場合、Ｃ１～Ｃ６のアルキル基における水素原子が、置換基Ｃによって任意に置換される。 The C1 to C6 alkyl group of the “C1 to C6 alkyl group optionally substituted with a substituent C” for R6 in the formula (1) has the same meaning as defined above, and is preferably a methyl group or an ethyl group. Or a propyl group, and more preferably a methyl group or an ethyl group. When it has the substituent C, the hydrogen atom in the C1 to C6 alkyl group is optionally substituted by the substituent C.
　式（１）のＲ６における「Ｃ１～Ｃ６のハロアルキル基」は、前記の定義と同義であり、好ましくは、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、３，３－ジフルオロプロピル基、または３，３，３－トリフルオロプロピル基であり、さらに好ましくは、ジフルオロメチル基、またはトリフルオロメチル基である。 The “C1 to C6 haloalkyl group” for R6 in the formula (1) is as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2 A trifluoroethyl group, a 3,3-difluoropropyl group or a 3,3,3-trifluoropropyl group, more preferably a difluoromethyl group or a trifluoromethyl group.
　式（１）のＲ６における「置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基」のＣ３～Ｃ８のシクロアルキル基は、前記の定義と同義であり、好ましくは、シクロプロピル基、シクロブチル基、シクロペンチル基、またはシクロヘキシル基であり、さらに好ましくは、シクロプロピル基、またはシクロブチル基である。置換基Ｃを有する場合、Ｃ３～Ｃ８のシクロアルキル基における水素原子が、置換基Ｃによって任意に置換される。 The C3-C8 cycloalkyl group of the "C3-C8 cycloalkyl group optionally substituted with a substituent C" for R6 in formula (1) has the same meaning as defined above, and is preferably a cyclopropyl group. , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group. When it has the substituent C, the hydrogen atom in the C3 to C8 cycloalkyl group is optionally substituted by the substituent C.
　式（１）のＲ６における「置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基」のＣ２～Ｃ６のアルケニル基は、前記の定義と同義であり、好ましくは、ビニル基、１－プロペニル基、またはアリル基であり、さらに好ましくは、ビニル基である。置換基Ｃを有する場合、Ｃ２～Ｃ６のアルケニル基における水素原子が、置換基Ｃによって任意に置換される。 The C2 to C6 alkenyl group of the “C2 to C6 alkenyl group optionally substituted by substituent C” for R6 in the formula (1) has the same meaning as described above, and is preferably a vinyl group, 1- It is a propenyl group or an allyl group, and more preferably a vinyl group. When it has the substituent C, the hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent C.
　式（１）のＲ６における「Ｃ２～Ｃ６のハロアルケニル基」は、前記の定義と同義であり、好ましくは、２－フルオロビニル基、２，２－ジフルオロビニル基、２，２－ジクロロビニル基、３－フルオロアリル基、３，３－ジフルオロアリル基、または３，３－ジクロロアリル基であり、さらに好ましくは、２－フルオロビニル基、または２，２－ジフルオロビニル基である。 The “C2 to C6 haloalkenyl group” for R6 in the formula (1) is as defined above, and is preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group. , A 3-fluoroallyl group, a 3,3-difluoroallyl group, or a 3,3-dichloroallyl group, and more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.
　式（１）のＲ６における「置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基」のＣ２～Ｃ６のアルキニル基は、前記の定義と同義であり、好ましくは、エチニル基、１－プロピニル基、プロパルギル基、１－ブチニル基、２－ブチニル基、または３－ブチニル基であり、さらに好ましくは、エチニル基、１－プロピニル基、またはプロパルギル基である。置換基Ｃを有する場合、Ｃ２～Ｃ６のアルキニル基における水素原子が、置換基Ｃによって任意に置換される。 The C2 to C6 alkynyl groups of the “C2 to C6 alkynyl groups optionally substituted with the substituent C” for R6 in the formula (1) have the same meaning as described above, and are preferably an ethynyl group, 1- A propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, and more preferably an ethynyl group, a 1-propynyl group, or a propargyl group; When it has the substituent C, the hydrogen atom in the alkynyl group of C2 to C6 is optionally substituted by the substituent C.
　式（１）のＲ６における「Ｃ２～Ｃ６のハロアルキニル基」は、前記の定義と同義であり、好ましくは、３，３－ジフルオロ－１－プロピニル基、３，３，３－トリフルオロ－１－プロピニル基、４，４－ジフルオロ－１－ブチニル基、４，４－ジフルオロ－２－ブチニル基、４，４，４－トリフルオロ－１－ブチニル基、または４，４，４－トリフルオロ－２－ブチニル基であり、さらに好ましくは、３，３－ジフルオロ－１－プロピニル基、または３，３，３－トリフルオロ－１－プロピニル基である。 The “C2-C6 haloalkynyl group” in R6 of the formula (1) has the same meaning as defined above, and is preferably a 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -Propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- It is a 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group or a 3,3,3-trifluoro-1-propynyl group.
　式（１）のＲ６における「置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基」のＣ１～Ｃ６のアルコキシ基は、前記の定義と同義であり、好ましくは、メトキシ基、エトキシ基、プロピルオキシ基、またはイソプロピルオキシ基であり、さらに好ましくは、メトキシ基、またはエトキシ基である。置換基Ｃを有する場合、Ｃ１～Ｃ６のアルコキシ基における水素原子が、置換基Ｃによって任意に置換される。 The C1 to C6 alkoxy group of the "C1 to C6 alkoxy group optionally substituted with the substituent C" for R6 in the formula (1) has the same meaning as described above, and is preferably a methoxy group or an ethoxy group. , A propyloxy group or an isopropyloxy group, and more preferably a methoxy group or an ethoxy group. When it has the substituent C, the hydrogen atom in the C1-C6 alkoxy group is optionally substituted by the substituent C.
　式（１）のＲ６における「Ｃ１～Ｃ６のハロアルコキシ基」は、前記の定義と同義であり、好ましくは、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、３，３－ジフルオロプロピルオキシ基、または３，３，３－トリフルオロプロピルオキシ基であり、さらに好ましくは、ジフルオロメトキシ基、またはトリフルオロメトキシ基である The “C1 to C6 haloalkoxy group” for R6 in the formula (1) is as defined above, and is preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2 A 2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, or a 3,3,3-trifluoropropyloxy group, more preferably a difluoromethoxy group or a trifluoromethoxy group
　式（１）のＲ６における「置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基」のＣ３～Ｃ８のシクロアルコキシ基は、前記の定義と同義であり、好ましくは、シクロプロピルオキシ基、シクロブトキシ基、シクロペンチルオキシ基、またはシクロヘキシルオキシ基であり、さらに好ましくは、シクロプロピルオキシ基、またはシクロブトキシ基である。置換基Ｃを有する場合、Ｃ３～Ｃ８のシクロアルコキシ基における水素原子が、置換基Ｃによって任意に置換される。 The C3-C8 cycloalkoxy group of the “C3-C8 cycloalkoxy group optionally substituted with substituent C” for R6 in formula (1) has the same meaning as defined above, and is preferably cyclopropyloxy. A cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group, and more preferably a cyclopropyloxy group or a cyclobutoxy group. When it has the substituent C, the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent C.
　式（１）のＲ６における「置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基」のＣ２～Ｃ６のアルケニルオキシ基は、前記の定義と同義であり、好ましくは、ビニルオキシ基、１－プロペニルオキシ基、またはアリルオキシ基、さらに好ましくは、ビニルオキシ基である。置換基Ｃを有する場合、Ｃ２～Ｃ６のアルケニルオキシ基における水素原子が、置換基Ｃによって任意に置換される。 The C2 to C6 alkenyloxy group of the “C2 to C6 alkenyloxy group optionally substituted with the substituent C” for R6 in the formula (1) has the same meaning as defined above, and is preferably a vinyloxy group, A 1-propenyloxy group or an allyloxy group, more preferably a vinyloxy group. When it has the substituent C, the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent C.
　式（１）のＲ６における「Ｃ２～Ｃ６のハロアルケニルオキシ基」は、前記の定義と同義であり、好ましくは、２－フルオロビニルオキシ基、２，２－ジフルオロビニルオキシ基、２，２－ジクロロビニルオキシ基、３－フルオロアリルオキシ基、３，３－ジフルオロアリルオキシ基、または３，３－ジクロロアリルオキシ基であり、さらに好ましくは、２－フルオロビニルオキシ基、または２，２－ジフルオロビニルオキシ基である。 The “C2-C6 haloalkenyloxy group” for R6 in the formula (1) has the same meaning as defined above, and is preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2- A dichlorovinyloxy group, a 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group or a 3,3-dichloroallyloxy group, more preferably a 2-fluorovinyloxy group or a 2,2-difluoro It is a vinyloxy group.
　式（１）のＲ６における「置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基」のＣ３～Ｃ６のアルキニルオキシ基は、前記の定義と同義であり、好ましくは、プロパルギルオキシ基、２－ブチニルオキシ基、または３－ブチニルオキシ基であり、さらに好ましくは、プロパルギルオキシ基である。置換基Ｃを有する場合、Ｃ３～Ｃ６のアルキニルオキシ基における水素原子が、置換基Ｃによって任意に置換される。 The C3 to C6 alkynyloxy group of the "C3 to C6 alkynyloxy group optionally substituted with the substituent C" for R6 in the formula (1) is as defined above, and is preferably a propargyloxy group , A 2-butynyloxy group or a 3-butynyloxy group, and more preferably a propargyloxy group. When the compound has the substituent C, a hydrogen atom in the C3 to C6 alkynyloxy group is optionally substituted by the substituent C.
　式（１）のＲ６における「Ｃ３～Ｃ６のハロアルキニルオキシ基」は、前記の定義と同義であり、好ましくは、４，４－ジフルオロ－２－ブチニルオキシ基、４－クロロ－４，４－ジフルオロ－２－ブチニルオキシ基、４－ブロモ－４，４－ジフルオロ－２－ブチニルオキシ基、または４，４，４－トリフルオロ－２－ブチニルオキシ基であり、さらに好ましくは、４，４－ジフルオロ－２－ブチニルオキシ基、または４，４，４－トリフルオロ－２－ブチニルオキシ基である。 The “C3-C6 haloalkynyloxy group” in R6 of the formula (1) has the same meaning as defined above, and is preferably a 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- A butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.
　式（１）のＲ６における「置換基Ｄで適宜０～５置換されてもよいアリールオキシ基」のアリールオキシ基は、前記の定義と同義であり、好ましくは、フェノキシ基、またはナフチルオキシ基であり、さらに好ましくは、フェノキシ基である。置換基Ｄを有する場合、アリールオキシ基における水素原子が、置換基Ｄによって任意に置換される。ただし、２置換以上の置換基Ｄがある場合、それぞれは独立している。 The aryloxy group of the “aryloxy group optionally substituted with 0 to 5 substituent (s) D” in R6 of the formula (1) is as defined above, and is preferably a phenoxy group or a naphthyloxy group. And more preferably a phenoxy group. When it has the substituent D, the hydrogen atom in the aryloxy group is optionally substituted by the substituent D. However, when there are two or more substituents D, each is independent.
　式（１）のＲ６における「置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基」のヘテロアリールオキシ基は、前記の定義と同義であり、好ましくは、ピリジルオキシ基、ピリダジニルオキシ基、ピリミジニルオキシ基、ピラジニルオキシ基、トリアジニルオキシ基、テトラジニルオキシ基、チエニルオキシ基、チアゾリルオキシ基、イソチアゾリルオキシ基、チアジアゾリルオキシ基であり、さらに好ましくは、ピリジルオキシ基、ピリダジニルオキシ基、ピリミジニルオキシ基、ピラジニルオキシ基である。置換基Ｄを有する場合、ヘテロアリールオキシ基における水素原子が、置換基Ｄによって任意に置換される。ただし、２置換の置換基Ｄがある場合、それぞれは独立している。 The heteroaryloxy group of the “heteroaryloxy group optionally substituted with 0 to 2 substituent (s) D” for R 6 in the formula (1) is as defined above, and is preferably a pyridyloxy group or a pyridyl group. Dinyloxy group, pyrimidinyloxy group, pyrazinyloxy group, triazinyloxy group, tetrazinyloxy group, thienyloxy group, thiazolyloxy group, isothiazolyloxy group, thiadiazolyloxy group, more preferably pyridyl Oxy, pyridazinyloxy, pyrimidinyloxy and pyrazinyloxy groups. When the compound has the substituent D, a hydrogen atom in the heteroaryloxy group is optionally substituted by the substituent D. However, when there is a disubstituted substituent D, each is independent.
　式（１）のＲ６における「置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基」のアラルキルオキシ基は、前記の定義と同義であり、好ましくは、ベンジルオキシ基、フェネチルオキシ基、フェニルプロピルオキシ基であり、さらに好ましくは、ベンジルオキシ基、フェネチルオキシ基である。置換基Ｄを有する場合、アラルキルオキシ基における水素原子が、置換基Ｄによって任意に置換される。ただし、２置換以上の置換基Ｄがある場合、それぞれは独立している。 The aralkyloxy group of the “aralkyloxy group optionally substituted with 0 to 5 substituents D” in R6 of the formula (1) has the same meaning as described above, and is preferably a benzyloxy group, a phenethyloxy group, It is a phenylpropyloxy group, more preferably a benzyloxy group and a phenethyloxy group. When it has the substituent D, the hydrogen atom in the aralkyloxy group is optionally substituted by the substituent D. However, when there are two or more substituents D, each is independent.
　式（１）のＲ６における「Ｒｘ１Ｃ（＝Ｏ）－」のＲｘ１は、前記の定義と同義である。Ｒｘ１として、好ましくは、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のアルコキシ基である。「Ｒｘ１Ｃ（＝Ｏ）－」として、好ましくは、アセチル基、メトキシアセチル基、シアノアセチル基、プロピオニル基、ジフルオロアセチル基、トリフルオロアセチル基、シクロプロパンカルボニル基、メトキシカルボニル基、エトキシカルボニル基、２，２－ジフルオロエトキシカルボニル基、２，２，２－トリフルオロエトキシカルボニル基、３，３，３－トリフルオロプロピルオキシカルボニル基、シクロプロピルオキシカルボニル基、アミノカルボニル基、メチルアミノカルボニル基、エチルアミノカルボニル基、（メトキシメチル）アミノカルボニル基、（２－メトキシエチル）アミノカルボニル基、（シアノメチル）アミノカルボニル基、（２－シアノエチル）アミノカルボニル基、ジメチルアミノカルボニル基、エチルメチルアミノカルボニル基、ジエチルアミノカルボニル基、（メトキシメチル）メチルアミノカルボニル基、（２－メトキシエチル）メチルアミノカルボニル基、（シアノメチル）メチルアミノカルボニル基、（２－シアノエチル）メチルアミノカルボニル基、２，２－ジフルオロエチルアミノカルボニル基、２，２，２－トリフルオロエチルアミノカルボニル基、シクロプロピルアミノカルボニル基、（シクロプロピル）メチルアミノカルボニル基、ピロリジニルカルボニル基、またはピペリジニルカルボニル基であり、さらに好ましくは、アセチル基、メトキシアセチル基、シアノアセチル基、プロピオニル基、メトキシカルボニル基、またはエトキシカルボニル基である。 ＲRx1 of "Rx1C (= O)-" in R6 of the formula (1) is as defined above. Rx1 is preferably a C1 to C6 alkyl group or a C1 to C6 alkoxy group which may be appropriately substituted with the substituent B. As “Rx1C (＝ O) —”, preferably, acetyl, methoxyacetyl, cyanoacetyl, propionyl, difluoroacetyl, trifluoroacetyl, cyclopropanecarbonyl, methoxycarbonyl, ethoxycarbonyl, 2 , 2-Difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylamino Carbonyl group, (methoxymethyl) aminocarbonyl group, (2-methoxyethyl) aminocarbonyl group, (cyanomethyl) aminocarbonyl group, (2-cyanoethyl) aminocarbonyl group, dimethylaminocarbonyl group, ethylmethyl Minocarbonyl group, diethylaminocarbonyl group, (methoxymethyl) methylaminocarbonyl group, (2-methoxyethyl) methylaminocarbonyl group, (cyanomethyl) methylaminocarbonyl group, (2-cyanoethyl) methylaminocarbonyl group, 2,2- A difluoroethylaminocarbonyl group, a 2,2,2-trifluoroethylaminocarbonyl group, a cyclopropylaminocarbonyl group, a (cyclopropyl) methylaminocarbonyl group, a pyrrolidinylcarbonyl group, or a piperidinylcarbonyl group; Preferably, they are an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a methoxycarbonyl group, or an ethoxycarbonyl group.
　式（１）のＲ６における「Ｒｘ１Ｃ（＝Ｏ）Ｏ－」のＲｘ１は、前記の定義と同義である。Ｒｘ１として、好ましくは、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のアルコキシ基である。「Ｒｘ１Ｃ（＝Ｏ）Ｏ－」として、好ましくは、アセチルオキシ基、メトキシアセチルオキシ基、シアノアセチルオキシ基、プロピオニルオキシ基、ジフルオロアセチルオキシ基、トリフルオロアセチルオキシ基、シクロプロパンカルボニルオキシ基、メトキシカルボニルオキシ基、エトキシカルボニルオキシ基、２，２－ジフルオロエトキシカルボニルオキシ基、２，２，２－トリフルオロエトキシカルボニルオキシ基、３，３，３－トリフルオロプロピルオキシカルボニルオキシ基、シクロプロピルオキシカルボニルオキシ基、アミノカルボニルオキシ基、メチルアミノカルボニルオキシ基、エチルアミノカルボニルオキシ基、（メトキシメチル）アミノカルボニルオキシ基、（２－メトキシエチル）アミノカルボニルオキシ基、（シアノメチル）アミノカルボニルオキシ基、（２－シアノエチル）アミノカルボニルオキシ基、ジメチルアミノカルボニルオキシ基、エチルメチルアミノカルボニルオキシ基、ジエチルアミノカルボニルオキシ基、（メトキシメチル）メチルアミノカルボニルオキシ基、（２－メトキシエチル）メチルアミノカルボニルオキシ基、（シアノメチル）メチルアミノカルボニルオキシ基、（２－シアノエチル）メチルアミノカルボニルオキシ基、２，２－ジフルオロエチルアミノカルボニルオキシ基、２，２，２－トリフルオロエチルアミノカルボニルオキシ基、シクロプロピルアミノカルボニルオキシ基、（シクロプロピル）メチルアミノカルボニルオキシ基、ピロリジニルカルボニルオキシ基、またはピペリジニルカルボニルオキシ基であり、さらに好ましくは、アセチルオキシ基、メトキシアセチルオキシ基、シアノアセチルオキシ基、プロピオニルオキシ基、メトキシカルボニルオキシ基、またはエトキシカルボニルオキシ基である。 ＲRx1 of “Rx1C (＝ O) O—” in R6 of Formula (1) has the same meaning as the above definition. Rx1 is preferably a C1 to C6 alkyl group or a C1 to C6 alkoxy group which may be appropriately substituted with the substituent B. As “Rx1C (＝ O) O—”, preferably, acetyloxy, methoxyacetyloxy, cyanoacetyloxy, propionyloxy, difluoroacetyloxy, trifluoroacetyloxy, cyclopropanecarbonyloxy, methoxy Carbonyloxy group, ethoxycarbonyloxy group, 2,2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, 3,3,3-trifluoropropyloxycarbonyloxy group, cyclopropyloxycarbonyl Oxy group, aminocarbonyloxy group, methylaminocarbonyloxy group, ethylaminocarbonyloxy group, (methoxymethyl) aminocarbonyloxy group, (2-methoxyethyl) aminocarbonyloxy group, Methyl) aminocarbonyloxy group, (2-cyanoethyl) aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethylmethylaminocarbonyloxy group, diethylaminocarbonyloxy group, (methoxymethyl) methylaminocarbonyloxy group, (2-methoxyethyl ) Methylaminocarbonyloxy group, (cyanomethyl) methylaminocarbonyloxy group, (2-cyanoethyl) methylaminocarbonyloxy group, 2,2-difluoroethylaminocarbonyloxy group, 2,2,2-trifluoroethylaminocarbonyloxy A cyclopropylaminocarbonyloxy group, a (cyclopropyl) methylaminocarbonyloxy group, a pyrrolidinylcarbonyloxy group, or a piperidinylcarbonyloxy group; Preferably, the acetyloxy group, methoxyacetyl group, a cyano acetyloxy group, propionyloxy group, a methoxycarbonyl group or an ethoxycarbonyl group.
　式（１）のＲ６における「１～２個の酸素原子を含む３～６員環の基」は、前記の定義と同義であり、好ましくは、オキソラニル基、オキサニル基、１，３－ジオキソラニル基、または１，３－ジオキサニル基であり、さらに好ましくは、１，３－ジオキソラニル基、または１，３－ジオキサニル基である。 The “3- to 6-membered ring group containing 1 or 2 oxygen atoms” in R 6 of the formula (1) is as defined above, and is preferably an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group. Or a 1,3-dioxanyl group, and more preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.
　式（１）のＲ６における「Ｒｃ－Ｌ－」のＲｃおよびＬは、前記の定義と同義である。「Ｒｃ－Ｌ－」として、好ましくは、メチルチオ基、メタンスルフィニル基、メタンスルホニル基、トリフルオロメチルチオ基、トリフルオロメタンスルフィニル基、またはトリフルオロメタンスルホニル基であり、さらに好ましくは、メチルチオ基、メタンスルフィニル基、またはメタンスルホニル基である。 ＲRc and L of "Rc-L-" in R6 of the formula (1) are as defined above. "Rc-L-" is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group Or a methanesulfonyl group.
　式（１）のＲ６における「ＲａＲｂＮ－」のＲａおよびＲｂは、前記の定義と同義である。「ＲａＲｂＮ－」として、好ましくは、アミノ基、メチルアミノ基、エチルアミノ基、（メトキシメチル）アミノ基、（２－メトキシエチル）アミノ基、（シアノメチル）アミノ基、（２－シアノエチル）アミノ基、ジメチルアミノ基、エチルメチルアミノ基、ジエチルアミノ基、（メトキシメチル）メチルアミノ基、（２－メトキシエチル）メチルアミノ基、（シアノメチル）メチルアミノ基、（２－シアノエチル）メチルアミノ基、２，２－ジフルオロエチルアミノ基、２，２，２－トリフルオロエチルアミノ基、シクロプロピルアミノ基、（シクロプロピル）メチルアミノ基、ピロリジニル基、またはピペリジニル基であり、さらに好ましくは、ジメチルアミノ基、エチルメチルアミノ基、またはジエチルアミノ基である。 ＲRa and Rb of "RaRbN-" in R6 of the formula (1) are as defined above. As "RaRbN-", preferably, an amino group, a methylamino group, an ethylamino group, a (methoxymethyl) amino group, a (2-methoxyethyl) amino group, a (cyanomethyl) amino group, a (2-cyanoethyl) amino group, Dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, 2,2- A difluoroethylamino group, a 2,2,2-trifluoroethylamino group, a cyclopropylamino group, a (cyclopropyl) methylamino group, a pyrrolidinyl group, or a piperidinyl group, and more preferably a dimethylamino group or an ethylmethylamino group; Or a diethylamino group.
　式（１）のＲ６における「Ｒｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－」のＲｘ２およびＲｘ３は、前記の定義と同義である。Ｒｘ２として、好ましくは、水素原子、メチル基、メトキシメチル基、シアノメチル基、エチル基、ジフルオロメチル基、トリフルオロメチル基、シクロプロピル基、メトキシ基、エトキシ基、２，２－ジフルオロエトキシ、２，２，２－トリフルオロエトキシ基、シクロプロピルオキシ基、アミノ基、メチルアミノ基、エチルアミノ基、（メトキシメチル）アミノ基、（２－メトキシエチル）アミノ基、（シアノメチル）アミノ基、（２－シアノエチル）アミノ基、ジメチルアミノ基、エチルメチルアミノ基、ジエチルアミノ基、（メトキシメチル）メチルアミノ基、（２－メトキシエチル）メチルアミノ基、（シアノメチル）メチルアミノ基、（２－シアノエチル）メチルアミノ基、２，２－ジフルオロエチルアミノ基、２，２，２－トリフルオロエチルアミノ基、シクロプロピルアミノ基、（シクロプロピル）メチルアミノ基、ピロリジニル基、またはピペリジニル基であり、さらに好ましくは、水素原子、メチル基、メトキシメチル基、シアノメチル基、ジフルオロメチル基、トリフルオロメチル基、メトキシ基、エトキシ基、アミノ基、ジメチルアミノ基、エチルメチルアミノ基、またはジエチルアミノ基である。また、Ｒｘ３として、好ましくは、水素原子、メチル基、メトキシメチル基、エトキシメチル基、シアノメチル基、エチル基、２－メトキシエチル基、２－エトキシエチル基、２－シアノエチル基、プロピル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、またはシクロプロピル基であり、さらに好ましくは、水素原子、メチル基、メトキシメチル基、シアノメチル基、エチル基、２－メトキシエチル基、２，２－ジフルオロエチル基、または２，２，２－トリフルオロエチル基である。 ＲRx2 and Rx3 of “Rx2C (＝ O) N (Rx3)-” in R6 of the formula (1) are as defined above. Rx2 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a difluoromethyl group, a trifluoromethyl group, a cyclopropyl group, a methoxy group, an ethoxy group, a 2,2-difluoroethoxy, 2,2-trifluoroethoxy, cyclopropyloxy, amino, methylamino, ethylamino, (methoxymethyl) amino, (2-methoxyethyl) amino, (cyanomethyl) amino, (2- (Cyanoethyl) amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group 2,2-difluoroethylamino group, 2,2,2-to A fluoroethylamino group, a cyclopropylamino group, a (cyclopropyl) methylamino group, a pyrrolidinyl group, or a piperidinyl group, more preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, a difluoromethyl group, a trifluoromethyl group; A methyl group, a methoxy group, an ethoxy group, an amino group, a dimethylamino group, an ethylmethylamino group, or a diethylamino group. Rx3 is preferably a hydrogen atom, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-cyanoethyl group, a propyl group, A 2-difluoroethyl group, a 2,2,2-trifluoroethyl group, or a cyclopropyl group, more preferably a hydrogen atom, a methyl group, a methoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, It is a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.
　以下、式（１）のＹについて詳細に説明する。 Ｙ Hereinafter, Y in Expression (1) will be described in detail.
　Ｙは、式（ｙ－１）
Figure JPOXMLDOC01-appb-C000011
で表される部分構造を表す。 Y is the formula (y-1)
Figure JPOXMLDOC01-appb-C000011
Represents a partial structure represented by
　式（ｙ－１）のＲ６は、前記と同義である。 ＲR6 in formula (y-1) has the same meaning as described above.
　式（ｙ－１）のｎは、０～３の整数を表す。 Ｎ n in the formula (y-1) represents an integer of 0 to 3.
　式（ｙ－１）のｎが２以上の場合、２以上のＲ６は、それぞれ独立した置換基を表し、同一または異なっていてよく、任意に選択することができる。 When n in the formula (y-1) is 2 or more, two or more R6s each represent an independent substituent, which may be the same or different, and can be arbitrarily selected.
　Ｙは、式（ｙ－２）
Figure JPOXMLDOC01-appb-C000012
で表される部分構造を表す。 Y is the formula (y-2)
Figure JPOXMLDOC01-appb-C000012
Represents a partial structure represented by
　式（ｙ－２）のＲ６は、前記と同義である。 ＲR6 in the formula (y-2) has the same meaning as described above.
　式（ｙ－２）のｎは、０～３の整数を表す。 Ｎ n in the formula (y-2) represents an integer of 0 to 3.
　式（ｙ－２）のｎが２以上の場合、２以上のＲ６は、それぞれ独立した置換基を表し、同一または異なっていてよく、任意に選択することができる。 場合 When n in the formula (y-2) is 2 or more, two or more R6s each represent an independent substituent, which may be the same or different, and can be arbitrarily selected.
　式（１）における破線部を含む結合は、
Figure JPOXMLDOC01-appb-C000013
で表される箇所を表す。 The bond including the broken line part in the equation (1) is
Figure JPOXMLDOC01-appb-C000013
Represents a portion represented by.
　式（１）における破線部を含む結合は、二重結合または単結合を表す。好ましい破線部を含む結合は、二重結合である。 結合 The bond containing the broken line in Formula (1) represents a double bond or a single bond. A preferable bond containing a broken line is a double bond.
　式（１）における破線部を含む結合が二重結合の場合は、式（１ａ）
Figure JPOXMLDOC01-appb-C000014
（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、ＸおよびＹは、式（１）と同義である。）で表される化合物、またはその塩を表す。 When the bond containing the dashed line in the formula (1) is a double bond, the formula (1a)
Figure JPOXMLDOC01-appb-C000014
(Wherein, R1, R2, R3, R4, R5, X and Y have the same meanings as in formula (1)) or a salt thereof.
　式（１）における破線部を含む結合が単結合の場合は、式（１ｂ）
Figure JPOXMLDOC01-appb-C000015
（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、ＸおよびＹは、式（１）と同義である。）で表される化合物、またはその塩を表す。 In the case where the bond including the broken line in the formula (1) is a single bond, the formula (1b)
Figure JPOXMLDOC01-appb-C000015
(Wherein, R1, R2, R3, R4, R5, X and Y have the same meanings as in formula (1)) or a salt thereof.
　式（１ｂ）におけるＲ５が水素以外の置換基の場合、Ｒ体もしくはＳ体のどちらか一方のみ、またはＲ体とＳ体との任意の割合の混合物である。 Ｒ When R5 in the formula (1b) is a substituent other than hydrogen, it is either the R-form or the S-form alone, or a mixture of the R-form and the S-form at an arbitrary ratio.
　式（１）で表される化合物は、１個または２個の軸不斉を有することがある。この際の異性体比は、単独または任意の割合の混合比であり、特に限定されることはない。 化合物 The compound represented by the formula (1) may have one or two axial asymmetries. The isomer ratio at this time is a single ratio or a mixing ratio of an arbitrary ratio, and is not particularly limited.
　式（１）で表される化合物は、不斉原子を含むことがある。この際の異性体比は、単独または任意の割合の混合比であり、特に限定されることはない。 化合物 The compound represented by the formula (1) may contain an asymmetric atom. The isomer ratio at this time is a single ratio or a mixing ratio of an arbitrary ratio, and is not particularly limited.
　式（１）で表される化合物は、幾何異性体を含むことがある。この際の異性体比は、単独または任意の割合の混合比であり、特に限定されることはない。 化合物 The compound represented by the formula (1) may include a geometric isomer. The isomer ratio at this time is a single ratio or a mixing ratio of an arbitrary ratio, and is not particularly limited.
　式（１）で表される化合物は、塩を形成できることがある。塩酸、硫酸、酢酸、フマル酸、マレイン酸のような酸塩や、ナトリウム、カリウム、カルシウムのような金属塩等が例示されるが、農園芸用殺菌剤として使用できる限り、特に限定されることはない。 化合物 The compound represented by the formula (1) may form a salt in some cases. Acid salts such as hydrochloric acid, sulfuric acid, acetic acid, fumaric acid, and maleic acid, and metal salts such as sodium, potassium, and calcium are exemplified, but are not particularly limited as long as they can be used as agricultural and horticultural fungicides. There is no.
　式（１）の「置換基Ａ」は、水酸基、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）およびＲｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）からなる群から選択される少なくとも１種を表す。 The “substituent A” in the formula (1) includes a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a RaRbN- (Here, Ra and Rb have the same meanings as described above.) And Rc-L- (where Rc and L have the same meanings as described above).
　中でも置換基Ａは、シアノ基、Ｃ１～Ｃ６のアルコキシ基またはＲｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）が好ましく、
　特に、シアノ基またはＣ１～Ｃ６のアルコキシ基が好ましい。 Among them, the substituent A is preferably a cyano group, a C1 to C6 alkoxy group or Rc-L- (where Rc and L are as defined above),
Particularly, a cyano group or a C1 to C6 alkoxy group is preferable.
　なお、置換基Ａの各用語は前記の定義と同義である。 The terms of the substituent A are as defined above.
　置換基Ａの好ましい具体例に関しては、水酸基；シアノ基；
Ｃ３～Ｃ８のシクロアルキル基として、シクロプロピル基、シクロブチル基、シクロペンチル基、およびシクロヘキシル基；
Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、エトキシ基、プロピルオキシ基、およびイソプロピルオキシ基；
Ｃ１～Ｃ６のハロアルコキシ基として、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、３，３－ジフルオロプロピルオキシ基、および３，３，３－トリフルオロプロピルオキシ基；
Ｃ３～Ｃ８のシクロアルコキシ基として、シクロプロピルオキシ基、シクロブトキシ基、シクロペンチルオキシ基、およびシクロヘキシルオキシ基；
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）として、アミノ基、メチルアミノ基、エチルアミノ基、（メトキシメチル）アミノ基、（２－メトキシエチル）アミノ基、（シアノメチル）アミノ基、（２－シアノエチル）アミノ基、ジメチルアミノ基、エチルメチルアミノ基、ジエチルアミノ基、（メトキシメチル）メチルアミノ基、（２－メトキシエチル）メチルアミノ基、（シアノメチル）メチルアミノ基、（２－シアノエチル）メチルアミノ基、２，２－ジフルオロエチルアミノ基、２，２，２－トリフルオロエチルアミノ基、シクロプロピルアミノ基、（シクロプロピル）メチルアミノ基、ピロリジニル基、およびピペリジニル基；
ならびにＲｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）として、メチルチオ基、メタンスルフィニル基、メタンスルホニル基、トリフルオロメチルチオ基、トリフルオロメタンスルフィニル基、およびトリフルオロメタンスルホニル基が挙げられる。 For preferred specific examples of the substituent A, a hydroxyl group; a cyano group;
C3-C8 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
A C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group;
C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
A C3-C8 cycloalkoxy group such as a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group;
RaRbN- (where Ra and Rb have the same meanings as described above) include amino, methylamino, ethylamino, (methoxymethyl) amino, (2-methoxyethyl) amino, (cyanomethyl) Amino group, (2-cyanoethyl) amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2 -Cyanoethyl) methylamino group, 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl) methylamino group, pyrrolidinyl group, and piperidinyl group;
And Rc-L- (where Rc and L have the same meanings as described above) include a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group. No.
　置換基Ａのさらに好ましい具体例に関しては、水酸基；シアノ基；
Ｃ３～Ｃ８のシクロアルキル基として、シクロプロピル基、およびシクロブチル基；
Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、およびエトキシ基；
Ｃ１～Ｃ６のハロアルコキシ基として、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、および２，２，２－トリフルオロエトキシ基；
Ｃ３～Ｃ８のシクロアルコキシ基として、シクロプロピルオキシ基、およびシクロブトキシ基；
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）として、ジメチルアミノ基、エチルメチルアミノ基、およびジエチルアミノ基；
ならびにＲｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）として、メチルチオ基、メタンスルフィニル基、およびメタンスルホニル基が挙げられる。 For more preferred specific examples of the substituent A, a hydroxyl group; a cyano group;
A C3-C8 cycloalkyl group such as a cyclopropyl group and a cyclobutyl group;
A methoxy group and an ethoxy group as the C1-C6 alkoxy group;
A C1-C6 haloalkoxy group such as a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group;
A C3-C8 cycloalkoxy group such as a cyclopropyloxy group and a cyclobutoxy group;
RaRbN- (where Ra and Rb are as defined above), such as a dimethylamino group, an ethylmethylamino group, and a diethylamino group;
And Rc-L- (where Rc and L have the same meanings as described above) include a methylthio group, a methanesulfinyl group, and a methanesulfonyl group.
　式（１）の「置換基Ｂ」は、シアノ基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種を表す。 「“ Substituent B ”in formula (1) represents at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group.
　中でも置換基Ｂは、シアノ基またはＣ１～Ｃ６のアルコキシ基が好ましい。 Among them, the substituent B is preferably a cyano group or a C1 to C6 alkoxy group.
　なお、置換基Ｂの各用語は前記の定義と同義である。 The terms of the substituent B are as defined above.
　置換基Ｂの好ましい具体例に関しては、シアノ基；
Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、エトキシ基、プロピルオキシ基、およびイソプロピルオキシ基；
Ｃ１～Ｃ６のハロアルコキシ基として、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、３，３－ジフルオロプロピルオキシ基、および３，３，３－トリフルオロプロピルオキシ基；
ならびにＣ３～Ｃ８のシクロアルコキシ基として、シクロプロピルオキシ基、シクロブトキシ基、シクロペンチルオキシ基、およびシクロヘキシルオキシ基が挙げられる。 For preferred specific examples of the substituent B, a cyano group;
A C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group;
C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
And C3-C8 cycloalkoxy groups include cyclopropyloxy, cyclobutoxy, cyclopentyloxy, and cyclohexyloxy groups.
　置換基Ｂのさらに好ましい具体例に関しては、シアノ基；
Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、およびエトキシ基；
Ｃ１～Ｃ６のハロアルコキシ基として、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、および２，２，２－トリフルオロエトキシ基；
ならびにＣ３～Ｃ８のシクロアルコキシ基として、シクロプロピルオキシ基、およびシクロブトキシ基が挙げられる。 For more preferred specific examples of the substituent B, a cyano group;
A methoxy group and an ethoxy group as the C1-C6 alkoxy group;
A C1-C6 haloalkoxy group such as a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group;
And the C3-C8 cycloalkoxy group includes a cyclopropyloxy group and a cyclobutoxy group.
　式（１）の「置換基Ｃ」とは、水酸基、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、Ｃ２～Ｃ６のアルコキシアルコキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、ＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記のＲｘ１と同義である。）および１～２個の酸素原子を含む３～６員環の基からなる群から選択される少なくとも１種を表し、 The “substituent C” in the formula (1) includes a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2 A C6 alkoxyalkoxy group, RaRbN- (where Ra and Rb are as defined above), Rc-L- (where Rc and L are as defined above), RdC (= O)-(where Rd is as defined above for Rx1) and at least one selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms,
　中でも置換基Ｃは、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、ＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記のＲｘ１と同義である。）または１～２個の酸素原子を含む３～６員環の基が好ましく、
　特に、シアノ基、Ｃ１～Ｃ６のアルコキシ基、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）または１～２個の酸素原子を含む３～６員環の基が好ましい。 Among them, the substituent C is a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, Rc-L- (where Rc and L are as defined above). ), RdC (= O)-(where Rd is as defined above for Rx1) or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms,
In particular, a cyano group, a C1-C6 alkoxy group, Rc-L- (where Rc and L are as defined above) or a 3- to 6-membered ring group containing 1-2 oxygen atoms is preferred. preferable.
　なお、置換基Ｃの各用語は前記の定義と同義である。 The terms of the substituent C are as defined above.
　置換基Ｃの好ましい具体例に関しては、水酸基；シアノ基；
Ｃ３～Ｃ８のシクロアルキル基として、シクロプロピル基、シクロブチル基、シクロペンチル基、およびシクロヘキシル基；
Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ブトキシ基、イソブトキシ基、およびｔ－ブトキシ基；
Ｃ１～Ｃ６のハロアルコキシ基として、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、３，３－ジフルオロプロピルオキシ基、および３，３，３－トリフルオロプロピルオキシ基；
Ｃ３～Ｃ８のシクロアルコキシ基として、シクロプロピルオキシ基、シクロブトキシ基、シクロペンチルオキシ基、およびシクロヘキシルオキシ基；
Ｃ２～Ｃ６のアルコキシアルコキシ基として、メトキシメトキシ基、エトキシメトキシ基、メトキシエトキシ基、エトキシエトキシ基、およびメトキシプロピルオキシ基；
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）として、アミノ基、メチルアミノ基、エチルアミノ基、（メトキシメチル）アミノ基、（２－メトキシエチル）アミノ基、（シアノメチル）アミノ基、（２－シアノエチル）アミノ基、ジメチルアミノ基、エチルメチルアミノ基、ジエチルアミノ基、（メトキシメチル）メチルアミノ基、（２－メトキシエチル）メチルアミノ基、（シアノメチル）メチルアミノ基、（２－シアノエチル）メチルアミノ基、２，２－ジフルオロエチルアミノ基、２，２，２－トリフルオロエチルアミノ基、シクロプロピルアミノ基、（シクロプロピル）メチルアミノ基、ピロリジニル基、およびピペリジニル基；
Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）として、メチルチオ基、メタンスルフィニル基、メタンスルホニル基、トリフルオロメチルチオ基、トリフルオロメタンスルフィニル基、およびトリフルオロメタンスルホニル基；
ＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記のＲｘ１と同義である。）として、アセチル基、メトキシアセチル基、シアノアセチル基、プロピオニル基、ジフルオロアセチル基、トリフルオロアセチル基、シクロプロパンカルボニル基、メトキシカルボニル基、エトキシカルボニル基、２，２－ジフルオロエトキシカルボニル基、２，２，２－トリフルオロエトキシカルボニル基、３，３，３－トリフルオロプロピルオキシカルボニル基、シクロプロピルオキシカルボニル基、アミノカルボニル基、メチルアミノカルボニル基、エチルアミノカルボニル基、（メトキシメチル）アミノカルボニル基、（２－メトキシエチル）アミノカルボニル基、（シアノメチル）アミノカルボニル基、（２－シアノエチル）アミノカルボニル基、ジメチルアミノカルボニル基、エチルメチルアミノカルボニル基、ジエチルアミノカルボニル基、（メトキシメチル）メチルアミノカルボニル基、（２－メトキシエチル）メチルアミノカルボニル基、（シアノメチル）メチルアミノカルボニル基、（２－シアノエチル）メチルアミノカルボニル基、２，２－ジフルオロエチルアミノカルボニル基、２，２，２－トリフルオロエチルアミノカルボニル基、シクロプロピルアミノカルボニル基、（シクロプロピル）メチルアミノカルボニル基、ピロリジニルカルボニル基、およびピペリジニルカルボニル基；
ならびに１～２個の酸素原子を含む３～６員環の基として、オキソラニル基、オキサニル基、１，３－ジオキソラニル基、および１，３－ジオキサニル基が挙げられる。 For preferred specific examples of the substituent C, a hydroxyl group; a cyano group;
C3-C8 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
A C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, and a t-butoxy group;
C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
A C3-C8 cycloalkoxy group such as a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group;
A C2-C6 alkoxyalkoxy group such as a methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, an ethoxyethoxy group, and a methoxypropyloxy group;
RaRbN- (where Ra and Rb have the same meanings as described above) include amino, methylamino, ethylamino, (methoxymethyl) amino, (2-methoxyethyl) amino, (cyanomethyl) Amino group, (2-cyanoethyl) amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2 -Cyanoethyl) methylamino group, 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl) methylamino group, pyrrolidinyl group, and piperidinyl group;
Rc-L- (where Rc and L have the same meanings as described above) as a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group;
RdC (= O)-(where Rd has the same meaning as Rx1 above) as an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl Group, methoxycarbonyl group, ethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, Aminocarbonyl group, methylaminocarbonyl group, ethylaminocarbonyl group, (methoxymethyl) aminocarbonyl group, (2-methoxyethyl) aminocarbonyl group, (cyanomethyl) aminocarbonyl group, (2-cyanoethyl) aminocarbonyl group, dimethylamino Carbonyl group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, (methoxymethyl) methylaminocarbonyl group, (2-methoxyethyl) methylaminocarbonyl group, (cyanomethyl) methylaminocarbonyl group, (2-cyanoethyl) methylaminocarbonyl group 2,2-difluoroethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl) methylaminocarbonyl group, pyrrolidinylcarbonyl group, and piperidinylcarbonyl Group;
In addition, examples of the 3- to 6-membered ring group containing one or two oxygen atoms include an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group, and a 1,3-dioxanyl group.
　置換基Ｃのさらに好ましい具体例に関しては、水酸基；シアノ基；
Ｃ３～Ｃ８のシクロアルキル基として、シクロプロピル基、およびシクロブチル基；
Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、およびエトキシ基；
Ｃ１～Ｃ６のハロアルコキシ基として、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基；
Ｃ３～Ｃ８のシクロアルコキシ基として、シクロプロピルオキシ基、シクロブトキシ基；
Ｃ２～Ｃ６のアルコキシアルコキシ基として、メトキシメトキシ基、エトキシメトキシ基、メトキシエトキシ基、およびエトキシエトキシ基；
ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）として、ジメチルアミノ基、エチルメチルアミノ基、およびジエチルアミノ基；
Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）として、メチルチオ基、メタンスルフィニル基、およびメタンスルホニル基；
ＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記のＲｘ１と同義である。）として、アセチル基、メトキシアセチル基、シアノアセチル基、ジフルオロアセチル基、トリフルオロアセチル基、メトキシカルボニル基、エトキシカルボニル基、アミノカルボニル基、ジメチルアミノカルボニル基、エチルメチルアミノカルボニル基、およびジエチルアミノカルボニル基；
ならびに１～２個の酸素原子を含む３～６員環の基として、１，３－ジオキソラニル基、および１，３－ジオキサニル基が挙げられる。 For more preferred specific examples of the substituent C, a hydroxyl group; a cyano group;
A C3-C8 cycloalkyl group such as a cyclopropyl group and a cyclobutyl group;
A methoxy group and an ethoxy group as the C1-C6 alkoxy group;
A C1-C6 haloalkoxy group such as a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group;
A C3-C8 cycloalkoxy group such as a cyclopropyloxy group or a cyclobutoxy group;
A C2-C6 alkoxyalkoxy group such as a methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, and an ethoxyethoxy group;
RaRbN- (where Ra and Rb are as defined above), such as a dimethylamino group, an ethylmethylamino group, and a diethylamino group;
Rc-L- (where Rc and L are as defined above), such as a methylthio group, a methanesulfinyl group, and a methanesulfonyl group;
RdC (= O)-(where Rd is as defined above for Rx1), acetyl, methoxyacetyl, cyanoacetyl, difluoroacetyl, trifluoroacetyl, methoxycarbonyl, ethoxycarbonyl A group, an aminocarbonyl group, a dimethylaminocarbonyl group, an ethylmethylaminocarbonyl group, and a diethylaminocarbonyl group;
Examples of the 3- to 6-membered ring group containing one or two oxygen atoms include a 1,3-dioxolanyl group and a 1,3-dioxanyl group.
　式（１）の「置換基Ｄ」とは、ハロゲン原子、水酸基、シアノ基、ニトロ基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種を表す。 The “substituent D” in the formula (1) includes a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C6 It represents at least one selected from the group consisting of a C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group and a C3 to C8 cycloalkoxy group.
　中でも置換基Ｄは、ハロゲン原子、シアノ基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ１～Ｃ６のアルコキシ基またはＣ１～Ｃ６のハロアルコキシ基が好ましく、
　特に、ハロゲン原子またはＣ１～Ｃ６のハロアルキル基が好ましい。 Among them, the substituent D is a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group or a C1-C6 haloalkoxy group which may be appropriately substituted with the substituent B. Is preferred,
Particularly, a halogen atom or a C1 to C6 haloalkyl group is preferable.
　なお、置換基Ｄの各用語は前記の定義と同義である。また、置換基Ｄにおける「置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基」に関しては、置換基Ｂを有する場合、Ｃ１～Ｃ６のアルキル基における水素原子が、置換基Ｂによって任意に置換される。 The terms of the substituent D are as defined above. Regarding the “C1 to C6 alkyl group optionally substituted with the substituent B” in the substituent D, when the compound has the substituent B, the hydrogen atom in the C1 to C6 alkyl group is optional depending on the substituent B. Is replaced by
　置換基Ｄの好ましい具体例に関しては、
ハロゲン原子として、フッ素原子、塩素原子、臭素原子およびヨウ素原子；
水酸基；シアノ基；ニトロ基；
置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基として、メチル基、メトキシメチル基、エトキシメチル基、シアノメチル基、エチル基、２－メトキシエチル基、２－エトキシエチル基、２－シアノエチル基、プロピル基、イソプロピル基、ブチル基、およびイソブチル基；
Ｃ１～Ｃ６のハロアルキル基として、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、２，２，２－トリフルオロエチル基、３，３－ジフルオロプロピル基、および３，３，３－トリフルオロプロピル基；
Ｃ３～Ｃ８のシクロアルキル基として、シクロプロピル基、シクロブチル基、シクロペンチル基、およびシクロヘキシル基；
Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ブトキシ基、イソブトキシ基、およびｔ－ブトキシ基；
Ｃ１～Ｃ６のハロアルコキシ基として、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、３，３－ジフルオロプロピルオキシ基、および３，３，３－トリフルオロプロピルオキシ基；
ならびにＣ３～Ｃ８のシクロアルコキシ基として、シクロプロピルオキシ基、シクロブトキシ基、シクロペンチルオキシ基、およびシクロヘキシルオキシ基が挙げられる。 For preferred specific examples of substituent D,
As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom;
Hydroxyl group; cyano group; nitro group;
Examples of the C1-C6 alkyl group optionally substituted with the substituent B include a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, and a 2-cyanoethyl group. Groups, propyl, isopropyl, butyl, and isobutyl groups;
C1-C6 haloalkyl groups include difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3-difluoropropyl, and 3,3,3 A trifluoropropyl group;
C3-C8 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
A C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, and a t-butoxy group;
C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
And C3-C8 cycloalkoxy groups include cyclopropyloxy, cyclobutoxy, cyclopentyloxy, and cyclohexyloxy groups.
　置換基Ｄのさらに好ましい具体例に関しては、
ハロゲン原子として、フッ素原子、塩素原子、および臭素原子；
水酸基；シアノ基；ニトロ基；
置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基として、メチル基、メトキシメチル基、エトキシメチル基、シアノメチル基、エチル基、２－メトキシエチル基、２－エトキシエチル基、および２－シアノエチル基；
Ｃ１～Ｃ６のハロアルキル基として、ジフルオロメチル基、トリフルオロメチル基、２，２－ジフルオロエチル基、および２，２，２－トリフルオロエチル基；
Ｃ３～Ｃ８のシクロアルキル基として、シクロプロピル基、およびシクロブチル基；
Ｃ１～Ｃ６のアルコキシ基として、メトキシ基、エトキシ基、プロピルオキシ基、およびイソプロピルオキシ基；
Ｃ１～Ｃ６のハロアルコキシ基として、ジフルオロメトキシ基、トリフルオロメトキシ基、２，２－ジフルオロエトキシ基、および２，２，２－トリフルオロエトキシ基；
ならびにＣ３～Ｃ８のシクロアルコキシ基として、シクロプロピルオキシ基およびシクロブトキシ基が挙げられる。 For more preferred specific examples of the substituent D,
As a halogen atom, a fluorine atom, a chlorine atom, and a bromine atom;
Hydroxyl group; cyano group; nitro group;
Examples of the C1-C6 alkyl group optionally substituted with the substituent B include a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, and a 2-alkyl group. A cyanoethyl group;
A C1-C6 haloalkyl group such as a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, and a 2,2,2-trifluoroethyl group;
A C3-C8 cycloalkyl group such as a cyclopropyl group and a cyclobutyl group;
A C1-C6 alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group;
A C1-C6 haloalkoxy group such as a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group;
And C3-C8 cycloalkoxy groups include cyclopropyloxy and cyclobutoxy groups.
　以上説明したＲ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｘ、Ｙ、破線部、置換基Ａ、置換基Ｂ、置換基Ｃおよび置換基Ｄにおける好ましい範囲を任意に組み合わせて得られる全ての化合物の範囲も本発明の式（１）で表される化合物の範囲として、本明細書に記載されているものとする。 All compounds obtained by arbitrarily combining the preferred ranges of R1, R2, R3, R4, R5, R6, X, Y, the broken line portion, the substituent A, the substituent B, the substituent C, and the substituent D described above. Is also described in the present specification as the range of the compound represented by the formula (1) of the present invention.
　次に、本発明の具体的な化合物は、表１に示す構造式（Ｐ－１～Ｐ－６１６）と、表２に示すＹ（Ｙ－１～Ｙ－９１０）と、酸素原子または硫黄原子であるＸとの組み合わせによって表される。これらの化合物は例示のためのものであって、本発明はこれらに限定されるものではない。 Next, specific compounds of the present invention include structural formulas (P-1 to P-616) shown in Table 1, Y (Y-1 to Y-910) shown in Table 2, an oxygen atom or a sulfur atom. Is represented by a combination with X. These compounds are for illustration only and the invention is not limited thereto.
Figure JPOXMLDOC01-appb-T000016
Figure JPOXMLDOC01-appb-T000016
Figure JPOXMLDOC01-appb-T000017
Figure JPOXMLDOC01-appb-T000017
Figure JPOXMLDOC01-appb-T000018
Figure JPOXMLDOC01-appb-T000018
Figure JPOXMLDOC01-appb-T000019
Figure JPOXMLDOC01-appb-T000019
Figure JPOXMLDOC01-appb-T000020
Figure JPOXMLDOC01-appb-T000020
Figure JPOXMLDOC01-appb-T000021
Figure JPOXMLDOC01-appb-T000021
Figure JPOXMLDOC01-appb-T000022
Figure JPOXMLDOC01-appb-T000022
Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000027
Figure JPOXMLDOC01-appb-T000027
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-T000031
Figure JPOXMLDOC01-appb-T000031
Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000034
Figure JPOXMLDOC01-appb-T000034
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000036
Figure JPOXMLDOC01-appb-T000036
Figure JPOXMLDOC01-appb-T000037
Figure JPOXMLDOC01-appb-T000037
Figure JPOXMLDOC01-appb-T000038
Figure JPOXMLDOC01-appb-T000038
Figure JPOXMLDOC01-appb-T000039
Figure JPOXMLDOC01-appb-T000039
Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-T000041
Figure JPOXMLDOC01-appb-T000041
　以下、例えば、表２中の「２－Ｔｈｉｏ」との記載は、２位で式（１）のピリドン環部分と結合するチオフェン－２－イル基を表し、「３－Ｔｈｉｏ」との記載は、３位で式（１）のピリドン環部分と結合するチオフェン－３－イル基を表す。「２－Ｆ－３－Ｔｈｉｏ」との記載は、２位にフッ素原子が結合しているチオフェン－３－イル基であることを意味し、「４－Ｃｌ－５－Ｆ－３－Ｔｈｉｏ」との記載は、４位に塩素原子が結合し、５位にフッ素原子が結合しているチオフェン－３－イル基であることを意味し、「２，４－ｄｉ－Ｆ－３－Ｔｈｉｏ」との記載は、２位と４位にフッ素原子が結合しているチオフェン－３－イル基であることを意味し、他の記載も同様である。 Hereinafter, for example, the description “2-Thio” in Table 2 represents a thiophen-2-yl group bonded to the pyridone ring portion of the formula (1) at the 2-position, and the description “3-Thio” Represents a thiophen-3-yl group bonded to the pyridone ring moiety of the formula (1) at the 3-position. The description "2-F-3-Tio" means a thiophen-3-yl group having a fluorine atom bonded to the 2-position, and "4-Cl-5-F-3-Tio" Means a thiophen-3-yl group in which a chlorine atom is bonded to the 4-position and a fluorine atom is bonded to the 5-position, and "2,4-di-F-3-Thio" Means a thiophen-3-yl group having a fluorine atom bonded to the 2-position and 4-position, and the same applies to other descriptions.
Figure JPOXMLDOC01-appb-T000042
Figure JPOXMLDOC01-appb-T000042
Figure JPOXMLDOC01-appb-T000043
Figure JPOXMLDOC01-appb-T000043
Figure JPOXMLDOC01-appb-T000044
Figure JPOXMLDOC01-appb-T000044
Figure JPOXMLDOC01-appb-T000045
Figure JPOXMLDOC01-appb-T000045
Figure JPOXMLDOC01-appb-T000046
Figure JPOXMLDOC01-appb-T000046
Figure JPOXMLDOC01-appb-T000047
Figure JPOXMLDOC01-appb-T000047
Figure JPOXMLDOC01-appb-T000048
Figure JPOXMLDOC01-appb-T000048
Figure JPOXMLDOC01-appb-T000049
Figure JPOXMLDOC01-appb-T000049
Figure JPOXMLDOC01-appb-T000050
Figure JPOXMLDOC01-appb-T000050
　以下に、式（１）で表される化合物の製造方法を例示する。本発明化合物の製造方法は、製造方法Ａ～製造方法Ｖに限定されるものではない。 方法 The following describes a method for producing the compound represented by the formula (1). The production method of the compound of the present invention is not limited to Production Methods A to V.
［製造方法Ａ］
Figure JPOXMLDOC01-appb-C000051
 [Production method A]
Figure JPOXMLDOC01-appb-C000051
　式中、Ｒ９は、水素原子、水酸基、シアノ基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、Ｃ２～Ｃ６のハロアルケニルオキシ基、置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、Ｃ３～Ｃ６のハロアルキニルオキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表し、Ｒ８は、水素原子、またはＣ１～Ｃ６のアルキル基を表し、Ｒ２、Ｒ３、Ｒ４、Ｒ５、ＸおよびＹは前記と同義である。 In the formula, R9 represents a hydrogen atom, a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, or a C3 to C3 optionally substituted with a substituent A. A C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, C2- C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent A, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent A, substitution A C2-C6 alkenyloxy group optionally substituted with a group A, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with a substituent A, A 3-C6 haloalkynyloxy group, or RaRbN- (where Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 Represents a haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb, together with a nitrogen atom to be bonded, represent an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl, or azocanyl group R8 represents a hydrogen atom or a C1 to C6 alkyl group, and R2, R3, R4, R5, X and Y are as defined above.
　製造方法Ａは、本発明化合物および本発明化合物の製造中間体を含む式（１ｂ－ａ）で表される化合物を得る方法であって、式（３）で表される化合物とＲ９ＮＨ２とを、酸存在下で反応させることを含む製造方法である。 Production method A is a method for obtaining a compound represented by the formula containing a preparation intermediate of the compound of the present invention and the present invention compound (1b-a), a compound R9NH 2 represented by the formula (3) A reaction in the presence of an acid.
　本反応に使用するＲ９ＮＨ２は、市販品として入手または公知の方法で製造することができる。Ｒ９ＮＨ２は、塩酸、酢酸のような酸性化合物との塩を形成したものでもよく、目的とする反応が進行する限りにおいて特に限定されることはない。 R9NH 2 used in this reaction can be obtained as a commercial product or can be produced by a known method. R9NH 2 are hydrochloric, may be those forming a salt with an acidic compound such as acetic acid, it is not particularly limited as long as the reaction proceeds to the desired.
　本反応に使用するＲ９ＮＨ２は、式（３）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上２００当量以下である。 R9NH 2 used in this reaction may be at least 1 equivalent to the compound represented by the formula (3), and is not particularly limited as long as the desired reaction proceeds. It is equal to or more than 200 equivalents.
　本反応に使用する酸として、塩酸、硫酸等の無機酸類や、酢酸、メタンスルホン酸、ｐ－トルエンスルホン酸等の有機酸類が例示され、目的とする反応が進行する限りにおいて特に限定することはないが、好ましくは、酢酸である。また、Ｒ９ＮＨ２と酸性化合物との塩を使用する際には、酸の使用は必須ではない。 Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, methanesulfonic acid and p-toluenesulfonic acid, and are not particularly limited as long as the desired reaction proceeds. But not preferably acetic acid. Further, when using salts of R9NH 2 and the acidic compound, the use of acid is not essential.
　本反応に使用する酸の量は、Ｒ９ＮＨ２に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上２００当量以下である。また、使用する酸が液体である場合には、溶媒として使用することも可能である。 The amount of the acid used in this reaction may be 1 equivalent or more relative to R9NH 2 and is not particularly limited as long as the desired reaction proceeds, but is preferably 1 equivalent to 200 equivalents. is there. When the acid used is a liquid, it can be used as a solvent.
　本反応には溶媒を使用することができるが、必ずしも必須ではない。 溶媒 A solvent can be used for this reaction, but it is not essential.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、酢酸、メタンスルホン酸等の酸性系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。溶媒として、好ましくは、酸性系溶媒が挙げられ、さらに好ましくは、酢酸が挙げられる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but acidic solvents such as acetic acid and methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxy Ether solvents such as ethane, tetrahydrofuran and dioxane; alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ethyl acetate, isopropyl acetate and butyl acetate; Ester solvents, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, and urea solvents such as 1,3-dimethyl-2-imidazolidinone Dissolution , Dichloromethane, dichloroethane, chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The solvent is preferably an acidic solvent, and more preferably acetic acid.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（３）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (3). is there.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、５０℃以上１８０℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 50 ° C or higher and 180 ° C or lower or the boiling point of the solvent or lower.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 の 後 As the post-treatment of the reaction, liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
　前記で得られた式（１ｂ－ａ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (1ba) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（１ｂ－ａ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by the formula (1ba) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（１ｂ－ａ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by the formula (1ba) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
　製造方法Ａによると、式（１ｂ－ａ）で表される化合物においてＲ９が水素原子を表すときに製造することができる式（２）で表される化合物は、本発明化合物のうち、式（１ｂ）で表される化合物を得る有用な製造中間体となりうる。 According to the production method A, the compound represented by the formula (2) that can be produced when R9 represents a hydrogen atom in the compound represented by the formula (1ba) is a compound of the formula (1) It can be a useful production intermediate for obtaining the compound represented by 1b).
　式（２）で表される製造中間体の具体例は、表３に示す構造式（Ｉ－１～Ｉ－１５４）と、表２に示すＹ（Ｙ－１～Ｙ－９１０）と、酸素原子または硫黄原子であるＸとの組み合わせによって表される。これらの化合物は、例示のためのものであって、本発明はこれらに限定されるものではない。 Specific examples of the production intermediate represented by the formula (2) include structural formulas (I-1 to I-154) shown in Table 3, Y (Y-1 to Y-910) shown in Table 2, and oxygen It is represented by a combination with an atom or a sulfur atom X. These compounds are for illustration only and the invention is not limited thereto.
Figure JPOXMLDOC01-appb-T000052
Figure JPOXMLDOC01-appb-T000052
Figure JPOXMLDOC01-appb-T000053
Figure JPOXMLDOC01-appb-T000053
Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000056
Figure JPOXMLDOC01-appb-T000056
Figure JPOXMLDOC01-appb-T000057
Figure JPOXMLDOC01-appb-T000057
Figure JPOXMLDOC01-appb-T000058
Figure JPOXMLDOC01-appb-T000058
　この式（２）で表される化合物を製造中間体として利用し、本発明の式（１ｂ）を得る方法を説明する。 方法 A method for obtaining the formula (1b) of the present invention by utilizing the compound represented by the formula (2) as a production intermediate will be described.
［製造方法Ｂ］
Figure JPOXMLDOC01-appb-C000059
 [Production method B]
Figure JPOXMLDOC01-appb-C000059
　式中、Ｌｖはメタンスルホニル基、トリフルオロメタンスルホニル基、ｐ‐トルエンスルホニル基、ハロゲン原子等の脱離基を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、ＸおよびＹは、前記と同義である。 In the formula, Lv represents a leaving group such as a methanesulfonyl group, a trifluoromethanesulfonyl group, a p-toluenesulfonyl group, a halogen atom and the like, and R1, R2, R3, R4, R5, X and Y are as defined above. .
　製造方法Ｂは、式（１ｂ）で表される化合物を得る方法であって、式（２）で表される製造中間体とＲ１Ｌｖとを、塩基の存在下、溶媒中で反応させることを含む製造方法である。 The production method B is a method for obtaining a compound represented by the formula (1b), and comprises reacting the production intermediate represented by the formula (2) with R1Lv in a solvent in the presence of a base. It is a manufacturing method.
　本反応に使用するＲ１Ｌｖは、市販品として入手または公知の方法で製造することができる。 ＲR1Lv used in this reaction can be obtained as a commercial product or can be produced by a known method.
　本反応に使用するＲ１Ｌｖの量は、式（２）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of R1Lv used in this reaction may be 1 equivalent or more based on the compound represented by the formula (2), and is not particularly limited as long as the desired reaction proceeds. It is 1 equivalent or more and 10 equivalents or less.
　本反応に使用する塩基として、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、水素化ナトリウム等の無機塩基類が例示されるが、目的とする反応が進行する限りにおいて特に限定されることはない。 Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride, but are not particularly limited as long as the desired reaction proceeds. It will not be done.
　本反応に使用する塩基の量は、式（２）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of the base used in this reaction may be one equivalent or more based on the compound represented by the formula (2), and is not particularly limited as long as the desired reaction proceeds. It is 1 equivalent or more and 10 equivalents or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ジメチルスルホキシド、スルホラン等の硫黄系溶媒、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; Alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; Amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, Chloroform, halogenated solvents such as carbon tetrachloride, dimethyl sulfoxide, sulfur-based solvents such as sulfolane, acetone, methyl ethyl ketone, ketone solvents such as methyl isobutyl ketone. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（２）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (2). is there.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１５０℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 0 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 の 後 As the post-treatment of the reaction, liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
　前記で得られた式（１ｂ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (1b) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（１ｂ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 反 応 The reaction mixture containing the compound represented by the formula (1b) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（１ｂ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by formula (1b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
［製造方法Ｃ］
Figure JPOXMLDOC01-appb-C000060
 [Production method C]
Figure JPOXMLDOC01-appb-C000060
　式中、ＳＲは硫黄化剤を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５およびＹは、前記と同義である。 ＳＲIn the formula, SR represents a sulfurizing agent, and R1, R2, R3, R4, R5 and Y are as defined above.
　製造方法Ｃは、式（１ｂ）で表される化合物のうち、式（１ｂ－ｃ）で表される化合物を得る製造方法であって、式（１ｂ－ｂ）で表される化合物と硫黄化剤（ＳＲ）とを、溶媒中で反応させることを含む製造方法である。 The production method C is a production method for obtaining a compound represented by the formula (1bc) among the compounds represented by the formula (1b), wherein the compound represented by the formula (1bb) is A production method comprising reacting an agent (SR) in a solvent.
　本反応に使用する硫黄化剤としては、ローソン試薬（２，４－ビス（４－メトキシフェニル）－１，３－ジチア－２，４－ジホスフェタン－２，４－ジスルフィド）等が挙げられる。 硫黄 Examples of the sulfurizing agent used in this reaction include Lawesson's reagent (2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetane-2,4-disulfide).
　本反応に使用する硫黄化剤の量は、式（１ｂ－ｂ）で表される化合物に対して０．５当量以上あればよく、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of the sulfurizing agent used in this reaction may be at least 0.5 equivalent to the compound represented by the formula (1bb), and is not particularly limited as long as the desired reaction proceeds. However, it is preferably 1 equivalent or more and 10 equivalents or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; Benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene are exemplified. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１ｂ－ｂ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually at least 3 times by weight to 200 times by weight the compound represented by the formula (1bb). It is as follows.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、５０℃以上１８０℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 50 ° C or higher and 180 ° C or lower or the boiling point of the solvent or lower.
　反応の後処理としては、反応混合物に対して、水、もしくは適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。また、本反応においては、分液操作は必須ではない。 の 後 As the post-treatment of the reaction, a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. In this reaction, a liquid separation operation is not essential.
　前記で得られた式（１ｂ－ｃ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The obtained reaction mixture containing the compound represented by the formula (1bc) can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（１ｂ－ｃ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by the formula (1bc) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（１ｂ－ｃ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by the formula (1bc) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
［製造方法Ｄ］
Figure JPOXMLDOC01-appb-C000061
 [Production method D]
Figure JPOXMLDOC01-appb-C000061
　式中、Ｒ５ａは、置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｌｖ、ＸおよびＹは、前記と同義である。 In the formula, R5a is a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a substituent A represents a C2-C6 alkenyl group optionally substituted with A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with the substituent A, or a C2-C6 haloalkynyl group. , R1, R2, R3, R4, Lv, X and Y are as defined above.
　製造方法Ｄは、式（１ｂ）で表される化合物のうち、Ｒ５ａが置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基である式（１ｂ－ｅ）で表される化合物の合成方法であって、式（１ｂ－ｄ）で表される化合物とＲ５ａＬｖとを、塩基の存在下、溶媒中で反応させることを含む製造方法である。 In the production method D, among the compounds represented by the formula (1b), R5a is an alkyl group of C1 to C6, a haloalkyl group of C1 to C6, and a substituent A which are optionally substituted with a substituent A. A C3-C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 optionally substituted with a substituent A A method for synthesizing a compound represented by the formula (1b-e) which is an alkynyl group or a C2 to C6 haloalkynyl group, wherein the compound represented by the formula (1b-d) and R5aLv are linked to the presence of a base. The following is a production method including reacting in a solvent.
　本反応に使用するＲ５ａＬｖは、市販品として入手または公知の方法で製造することができる。 ＲR5aLv used in this reaction can be obtained as a commercial product or can be produced by a known method.
　本反応に使用するＲ５ａＬｖの量は、式（１ｂ－ｄ）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１．８当量以下である。 The amount of R5aLv used in this reaction may be at least 1 equivalent to the compound represented by the formula (1b-d), and is not particularly limited as long as the desired reaction proceeds, but is preferably Is not less than 1 equivalent and not more than 1.8 equivalents.
　本反応に使用する塩基として、水素化ナトリウム等の金属ヒドリド類、メチルリチウム、ブチルリチウム、ｓｅｃ－ブチルリチウム、ｔ－ブチルリチウム、ヘキシルリチウム等の有機リチウム類や、リチウムジイソプロピルアミド、ヘキサメチルジシラザンリチウム、ヘキサメチルジシラザンナトリウム、ヘキサメチルジシラザンカリウム等の金属アミド類が例示される。 As a base used in this reaction, metal hydrides such as sodium hydride, organic lithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, hexyllithium, lithium diisopropylamide, hexamethyldisilazane Metal amides such as lithium, sodium hexamethyldisilazane, and potassium hexamethyldisilazane are exemplified.
　本反応に使用する塩基の量は、式（１ｂ－ｄ）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of the base used in this reaction may be at least 1 equivalent to the compound represented by the formula (1b-d), and is not particularly limited as long as the desired reaction proceeds, but is preferably Is 1 equivalent or more and 10 equivalents or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; Examples thereof include benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１ｂ－ｄ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually at least 3 times by weight to 200 times by weight the compound represented by the formula (1b-d). It is as follows.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－８０℃以上１００℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually −80 ° C. or more and 100 ° C. or less or the boiling point of the solvent or less.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 の 後 As the post-treatment of the reaction, liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, etc. are dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. are dissolved, sodium thiosulfate, sulfurous acid An aqueous solution or a salt solution in which a salt containing a sulfur atom such as sodium is dissolved can be arbitrarily used. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane and chloroform, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane, may be added. It is possible. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
　前記で得られた式（１ｂ－ｅ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (1be) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（１ｂ－ｅ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 反 応 The reaction mixture containing the compound represented by the formula (1be) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（１ｂ－ｅ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by the formula (1be) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
［製造方法Ｅ］
Figure JPOXMLDOC01-appb-C000062
 [Production method E]
Figure JPOXMLDOC01-appb-C000062
　式中、Ｏｘは酸化剤を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、ＸおよびＹは、前記と同義である。 In the formula, Ox represents an oxidizing agent, and R1, R2, R3, R4, R5, X and Y are as defined above.
　製造方法Ｅは、式（１ａ）で表される化合物を得る方法であって、式（１ｂ）で表される化合物と酸化剤（Ｏｘ）とを、溶媒中で反応させることを含む製造方法である。 The production method E is a method for obtaining a compound represented by the formula (1a), and comprises reacting a compound represented by the formula (1b) with an oxidizing agent (Ox) in a solvent. is there.
　本反応に使用する酸化剤としては、二酸化マンガン等の金属酸化物類、２，３－ジクロロ－５，６－ジシアノ－ｐ－ベンゾキノン等のベンゾキノン類、アゾビスイソブチロニトリル、過酸化ベンゾイル等のラジカル開始剤とＮ－クロロスクシンイミド、Ｎ－ブロモスクシンイミド、Ｎ－ヨードスクシンイミド、１，３－ジクロロ－５，５－ジメチルヒダントイン、１，３－ジブロモ－５，５－ジメチルヒダントイン、１，３－ジヨード－５，５－ジメチルヒダントイン等のハロゲン化剤とを組み合わせたもの等を使用することができる。 The oxidizing agent used in this reaction includes metal oxides such as manganese dioxide, benzoquinones such as 2,3-dichloro-5,6-dicyano-p-benzoquinone, azobisisobutyronitrile, benzoyl peroxide and the like. A radical initiator and N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3- A combination with a halogenating agent such as diiodo-5,5-dimethylhydantoin or the like can be used.
　以下、酸化剤が金属酸化物類である方法について説明する。 Hereinafter, a method in which the oxidizing agent is a metal oxide will be described.
　本反応に使用する酸化剤の量は、式（１ｂ）に表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、１当量以上２００当量以下である。 The amount of the oxidizing agent used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1b). It is equal to or more than 200 equivalents.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, dichloromethane, dichloroethane, chloroform, Examples include a halogen-based solvent such as carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１ｂ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (1b). is there.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１５０℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 0 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
　反応の後処理としては、溶解していない金属類を濾過することにより除去することが可能である。さらに、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。また、本反応において、分液操作は必須ではない。 の 後 As a post-treatment of the reaction, metals that are not dissolved can be removed by filtration. Furthermore, a liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. In this reaction, a liquid separation operation is not essential.
　前記で得られた式（１ａ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (1a) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（１ａ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 反 応 The reaction mixture containing the compound represented by the formula (1a) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（１ａ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by the formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
　以下、酸化剤がベンゾキノン類である方法について説明する。 Hereinafter, a method in which the oxidizing agent is a benzoquinone will be described.
　本反応に使用する酸化剤の量は、式（１ｂ）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、１当量以上２０当量以下である。 The amount of the oxidizing agent used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1b). It is equal to or more than 20 equivalents.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene, dichloromethane, dichloroethane, chloroform, Examples include a halogen-based solvent such as carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１ｂ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (1b). is there.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１５０℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 0 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。また、本反応において、分液操作は必須ではない。 の 後 As the post-treatment of the reaction, liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. In this reaction, a liquid separation operation is not essential.
　前記で得られた式（１ａ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (1a) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（１ａ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 反 応 The reaction mixture containing the compound represented by the formula (1a) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（１ａ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by the formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
　以下、酸化剤がラジカル開始剤とハロゲン化剤との組み合わせである方法について説明する。 Hereinafter, a method in which the oxidizing agent is a combination of a radical initiator and a halogenating agent will be described.
　本反応に使用するラジカル開始剤とハロゲン化剤の量は、それぞれ、式（１ｂ）で表される化合物に対して０．０１当量以上と１．０当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはない。好ましくは、ラジカル開始剤が０．０１当量以上１当量以下であり、ハロゲン化剤が１当量以上３当量以下である。 If the amounts of the radical initiator and the halogenating agent used in this reaction are 0.01 equivalent or more and 1.0 equivalent or more with respect to the compound represented by the formula (1b), respectively, the desired reaction proceeds. There is no particular limitation as long as it does. Preferably, the amount of the radical initiator is from 0.01 to 1 equivalent, and the amount of the halogenating agent is from 1 to 3 equivalents.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、クロロベンゼン、ジクロロベンゼン等のハロゲン化ベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is preferably a halogenated benzene solvent such as chlorobenzene or dichlorobenzene, or an ester solvent such as ethyl acetate, isopropyl acetate or butyl acetate. Solvents include halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１ｂ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (1b). is there.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、２０℃以上１５０℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 20 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 の 後 As the post-treatment of the reaction, liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily. In the liquid separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate or butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, and chloroform, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane, may be added. It is possible. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
　前記で得られた式（１ａ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (1a) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（１ａ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 反 応 The reaction mixture containing the compound represented by the formula (1a) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（１ａ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by the formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
［製造方法Ｆ］
Figure JPOXMLDOC01-appb-C000063
 [Production method F]
Figure JPOXMLDOC01-appb-C000063
　式中、Ｒ５ｂはハロゲン原子を表し、ＨａｌＲはハロゲン化剤を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４、ＸおよびＹは前記と同義である。 In the formula, R5b represents a halogen atom, HalR represents a halogenating agent, and R1, R2, R3, R4, X and Y are as defined above.
　製造方法Ｆは、式（１ａ）で表される化合物のうち、Ｒ５ｂがハロゲン原子を表す式（１ａ－ｂ）で表される化合物を得る製造方法であって、式（１ａ－ａ）で表される化合物とハロゲン化剤（ＨａｌＲ）とを、溶媒中で反応させることを含む製造方法である。 Production method F is a method for obtaining a compound represented by the formula (1a-b) in which R5b represents a halogen atom among the compounds represented by the formula (1a). And a halogenating agent (HalR) in a solvent.
　本反応に使用するハロゲン化剤としては、セレクトロフルオル（Ｎ－フルオロ－Ｎ’－クロロメチル－トリエチレンジアミン　ビス（テトラフルオロボラート））、Ｎ－クロロスクシンイミド、Ｎ－ブロモスクシンイミド、Ｎ－ヨードスクシンイミド、１，３－ジクロロ－５，５－ジメチルヒダントイン、１，３－ジブロモ－５，５－ジメチルヒダントイン、１，３－ジヨード－５，５－ジメチルヒダントイン、臭素、ヨウ素等が挙げられる。 Examples of the halogenating agent used in this reaction include selectrofluor (N-fluoro-N′-chloromethyl-triethylenediamine bis (tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodo Succinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine and the like.
　本反応に使用するハロゲン化剤の量は、式（１ａ－ａ）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。ただし、ヒダントインを含むハロゲン化剤の量は、０．５当量以上あれば、目的とする反応が進行する限りにおいて特に制限されることはなく、好ましくは、１当量以上５当量以下である。 The amount of the halogenating agent used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1a-a). Preferably, it is 1 equivalent or more and 10 equivalents or less. However, the amount of the halogenating agent containing hydantoin is not particularly limited as long as the desired reaction proceeds as long as the amount is 0.5 equivalent or more, and preferably 1 equivalent to 5 equivalents.
　本反応に使用するハロゲン化剤がヨウ素化剤である場合、塩酸、硫酸等の無機酸類や、酢酸、トリフルオロ酢酸、メタンスルホン酸、トリフルオロメタンスルホン酸等の有機酸のような酸を加えることができる。 When the halogenating agent used in this reaction is an iodizing agent, an acid such as an inorganic acid such as hydrochloric acid or sulfuric acid or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid, or trifluoromethanesulfonic acid is added. Can be.
　本反応に使用するハロゲン化剤がヨウ素化剤である場合に使用する酸の量は、式（１ａ－ａ）で表される化合物に対して０．０１当量以上あれば、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、０．１当量以上３当量以下である。 If the amount of the acid used when the halogenating agent used in this reaction is an iodizing agent is 0.01 equivalent or more with respect to the compound represented by the formula (1a-a), the desired reaction can be achieved. There is no particular limitation as long as it proceeds, but it is preferably 0.1 equivalent or more and 3 equivalents or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、硫酸、酢酸、トリフルオロ酢酸、メタンスルホン酸、トリフルオロメタンスルホン酸等の酸性系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, and trifluoromethanesulfonic acid, and diethyl ether , Diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane and other ether solvents, methanol, ethanol, isopropanol and other alcohol solvents, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene and other benzene solvents Solvents such as ethyl acetate, isopropyl acetate, butyl acetate, etc., nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide 1,3-dimethyl-2-urea-based solvent-imidazolidinone, dichloromethane, dichloroethane, chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１ａ－ａ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 times or more and 200 times or more the compound represented by the formula (1a-a). It is as follows.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１５０℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 0 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 の 後 As the post-treatment of the reaction, liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
　前記で得られた式（１ａ－ｂ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (1a-b) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（１ａ－ｂ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by the formula (1a-b) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（１ａ－ｂ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by the formula (1a-b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
［製造方法Ｇ］
Figure JPOXMLDOC01-appb-C000064
 [Production method G]
Figure JPOXMLDOC01-appb-C000064
　式中、Ｊは酸素原子または硫黄原子を表し、Ｊが酸素原子の場合、Ｒ５ｃは置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニル基、またはＣ３～Ｃ６のハロアルキニル基を表し、Ｊが硫黄原子の場合、Ｒ５ｃはＣ１～Ｃ６のアルキル基またはＣ１～Ｃ６のハロアルキル基を表し、Ｑは水素原子または金属を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５ｂ、ＸおよびＹは前記と同義である。 In the formula, J represents an oxygen atom or a sulfur atom, and when J is an oxygen atom, R5c represents a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group optionally substituted, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 haloalkenyl group, C3 optionally substituted with substituent A Represents a C6 to alkynyl group or a C3 to C6 haloalkynyl group, and when J is a sulfur atom, R5c represents a C1 to C6 alkyl group or a C1 to C6 haloalkyl group; and Q represents a hydrogen atom or a metal. , R1, R2, R3, R4, R5b, X and Y are as defined above.
　製造方法Ｇは、式（１ａ）で表される化合物のうち、Ｊは酸素原子または硫黄原子を表し、Ｊが酸素原子の場合、Ｒ５ｃが置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニル基、またはＣ３～Ｃ６のハロアルキニル基を表し、Ｊが硫黄原子の場合、Ｒ５ｃはＣ１～Ｃ６のアルキル基またはＣ１～Ｃ６のハロアルキル基を表す式（１ａ－ｃ）で表される化合物の合成法であって、式（１ａ－ｂ）で表される化合物とＲ５ｃ－Ｊ－Ｑとを、遷移金属類の存在下に反応させるカップリング反応によって得ることを含む製造方法である。 In the production method G, among the compounds represented by the formula (1a), J represents an oxygen atom or a sulfur atom, and when J is an oxygen atom, R5c is a group represented by C1 to C6 which may be appropriately substituted with a substituent A. Alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group optionally substituted with substituent A, C2-C6 alkenyl group optionally substituted with substituent A, C2-C6 halo Represents an alkenyl group, a C3-C6 alkynyl group optionally substituted with a substituent A, or a C3-C6 haloalkynyl group, and when J is a sulfur atom, R5c represents a C1-C6 alkyl group or C1-C6. A method for synthesizing a compound represented by the formula (1a-c) representing a haloalkyl group represented by the formula (1a-b), wherein R5c-JQ is reacted with R5c-JQ in the presence of a transition metal Coupling to react It is a manufacturing method comprising by reaction.
　式（１ａ－ｂ）で表される化合物中、好ましいＲ５ｂは、塩素原子、臭素原子、またはヨウ素原子である。 中 In the compound represented by the formula (1a-b), preferred R5b is a chlorine atom, a bromine atom, or an iodine atom.
　本反応に使用するＲ５ｃ－Ｊ－Ｑは、市販品として入手または公知の方法で製造できる。好ましいＱは、水素原子、または、ナトリウム、カリウム等のアルカリ金属類である。 ＲR5c-JQ used in this reaction is commercially available or can be produced by a known method. Preferred Q is a hydrogen atom or an alkali metal such as sodium or potassium.
　本反応に使用するＲ５ｃ－Ｊ－Ｑの量は、式（１ａ－ｂ）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはない。Ｑが水素原子のときは、溶媒としても使用可能である。 The amount of R5c-JQ used in this reaction is not particularly limited as long as the amount of the compound represented by the formula (1a-b) is 1 equivalent or more, as long as the desired reaction proceeds. . When Q is a hydrogen atom, it can be used also as a solvent.
　本反応に使用する遷移金属類は、配位子を有してよく、酢酸パラジウム、［１，１’－ビス（ジフェニルホスフィノ）フェロセン］パラジウムジクロリド、トリス(ジベンジリデンアセトン)ジパラジウム、テトラキス（トリフェニルホスフィン）パラジウム、ビス（トリフェニルホスフィン）パラジウムジクロリド等のパラジウム類等である。 The transition metals used in this reaction may have a ligand and include palladium acetate, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, tris (dibenzylideneacetone) dipalladium, tetrakis ( And palladiums such as triphenylphosphine) palladium and bis (triphenylphosphine) palladium dichloride.
　本反応に使用する遷移金属類の量は、式（１ａ－ｂ）で表される化合物に対して０．００１当量以上１当量以下であるが、目的とする反応が進行する限りにおいて特に限定されることはない。 The amount of the transition metals used in this reaction is 0.001 equivalent or more and 1 equivalent or less based on the compound represented by the formula (1a-b), but is not particularly limited as long as the desired reaction proceeds. Never.
　本反応を効率的に進行させるために、トリフェニルホスフィン、１，１’－ビス（ジフェニルホスフィノ）フェロセン、２－ジシクロヘキシルホスフィノ－２’４’６’－トリイソプロピルビフェニル、２－ジ－ｔ－ブチルホスフィノ－２’４’６’－トリイソプロピルビフェニル等のホスフィン配位子を添加することができる。 To make this reaction proceed efficiently, triphenylphosphine, 1,1′-bis (diphenylphosphino) ferrocene, 2-dicyclohexylphosphino-2′4′6′-triisopropylbiphenyl, 2-di-t A phosphine ligand such as -butylphosphino-2'4'6'-triisopropylbiphenyl can be added.
　本反応に使用するホスフィン配位子の量は、式（１ａ－ｂ）で表される化合物に対して０．００１当量以上１当量以下であるが、目的とする反応が進行する限りにおいて特に限定されることはない。 The amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less based on the compound represented by the formula (1a-b), but is not particularly limited as long as the desired reaction proceeds. It will not be done.
　本反応に使用する塩基は、炭酸ナトリウム、炭酸カリウム、炭酸セシウムのような無機塩基類やトリエチルアミン、トリブチルアミン、ジイソプロピルエチルアミン等の有機塩基類等である。 塩 基 The base used in this reaction is an inorganic base such as sodium carbonate, potassium carbonate or cesium carbonate, or an organic base such as triethylamine, tributylamine or diisopropylethylamine.
　本反応に使用する塩基の量は、式（１ａ－ｂ）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上５０当量以下である。 The amount of the base used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1a-b), but is preferably 1 to 50 equivalents.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、Ｒ５ｃ－Ｊ－Ｈ（式中、Ｒ５ｃは前記と同義であり、Ｊは酸素原子である。）で表されるアルコール溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but R5c-JH (wherein R5c is as defined above, and J is an oxygen atom. ), Ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene. Is mentioned. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１ａ－ｂ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 times or more and 200 times or more the compound represented by the formula (1a-b). It is as follows.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、３０℃以上２００℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 30 ° C or more and 200 ° C or less or the boiling point of the solvent or less.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。また、濾過操作を行うことにより、不溶物を除去することも可能であるが必須ではない。 の 後 As the post-treatment of the reaction, liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. It is also possible, but not essential, to remove insolubles by performing a filtration operation.
　前記で得られた式（１ａ－ｃ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (1a-c) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（１ａ－ｃ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by the formula (1a-c) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（１ａ－ｃ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by formula (1a-c) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
［製造方法Ｈ］
Figure JPOXMLDOC01-appb-C000065
 [Production method H]
Figure JPOXMLDOC01-appb-C000065
　式中、Ｒ５ｄは置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、またはＣ２～Ｃ６のハロアルケニル基を表し、Ｒ５ｄ－Ｂは有機ボロン酸類を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５ｂ、ＸおよびＹは前記と同義である。 In the formula, R5d represents a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent A, a substituent A Represents an optionally substituted C2-C6 alkenyl group or a C2-C6 haloalkenyl group, R5d-B represents an organic boronic acid, and R1, R2, R3, R4, R5b, X and Y are as defined above. Is synonymous with
　製造方法Ｈは、式（１ａ）で表される化合物のうち、Ｒ５ｄが置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、またはＣ２～Ｃ６のハロアルケニル基である式（１ａ－ｄ）で表される化合物の合成方法であって、式（１ａ－ｂ）で表される化合物と有機ボロン酸類（Ｒ５ｄ－Ｂ）とを遷移金属類および塩基の存在下で反応させる鈴木－宮浦カップリングによって得ることを含む製造方法である。 In the production method H, among the compounds represented by the formula (1a), R5d is a C1-C6 alkyl group, a C1-C6 haloalkyl group or a substituent A, which may be appropriately substituted with a substituent A. A C3-C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent A, or a C2-C6 haloalkenyl group represented by the formula (1a-d). A process comprising the step of reacting a compound of formula (1a-b) with an organoboronic acid (R5d-B) in the presence of a transition metal and a base by Suzuki-Miyaura coupling. Is the way.
　式（１ａ－ｂ）中、好ましいＲ５ｂは、塩素原子、臭素原子、またはヨウ素原子である。 好 ま し い In the formula (1a-b), preferred R5b is a chlorine atom, a bromine atom, or an iodine atom.
　本反応に使用するＲ５ｄ－Ｂは、有機ボロン酸や有機ボロン酸エステル等の有機ボロン酸類を表し、市販品として入手または公知の方法で製造できる。 ＲR5d-B used in this reaction represents an organic boronic acid such as an organic boronic acid or an organic boronic ester, and can be obtained as a commercial product or can be produced by a known method.
　本反応に使用するＲ５ｄ－Ｂの量は、式（１ａ－ｂ）で表される化合物に対して、１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of R5d-B used in this reaction is not particularly limited as long as the desired reaction proceeds as long as the amount of the compound represented by the formula (1a-b) is 1 equivalent or more. Preferably, it is 1 equivalent or more and 10 equivalents or less.
　本反応に使用する遷移金属類は、パラジウム、ニッケル、ルテニウム等であり、配位子を有してよい。好ましくは、酢酸パラジウム、［１，１’－ビス（ジフェニルホスフィノ）フェロセン］パラジウムジクロリド、トリス(ジベンジリデンアセトン)ジパラジウム、テトラキス（トリフェニルホスフィン）パラジウム、ビス（トリフェニルホスフィン）パラジウムジクロリド等のパラジウム類が挙げられる。 遷移 The transition metals used in this reaction are palladium, nickel, ruthenium and the like, and may have a ligand. Preferably, palladium acetate, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, tris (dibenzylideneacetone) dipalladium, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride, etc. Palladium is mentioned.
　本反応に使用する遷移金属類の量は、式（１ａ－ｂ）で表される化合物に対して０．００１当量以上１当量以下であるが、目的とする反応が進行する限りにおいて特に限定されることはない。 The amount of the transition metals used in this reaction is 0.001 equivalent or more and 1 equivalent or less based on the compound represented by the formula (1a-b), but is not particularly limited as long as the desired reaction proceeds. Never.
　本反応を効率的に進行させるために、トリフェニルホスフィン、トリシクロヘキシルホスフィン等のホスフィン配位子を添加することができる。 ホ ス Phosphine ligands such as triphenylphosphine and tricyclohexylphosphine can be added to make this reaction proceed efficiently.
　本反応に使用するホスフィン配位子の量は、式（１ａ－ｂ）で表される化合物に対して０．００１当量以上１当量以下であるが、目的とする反応が進行する限りにおいて特に限定されることはない。 The amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less based on the compound represented by the formula (1a-b), but is not particularly limited as long as the desired reaction proceeds. It will not be done.
　本反応に使用する塩基は、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、リン酸三カリウムのような無機塩基類やナトリウムメトキシド、ナトリウムエトキシド、カリウム　ｔ－ブトキシド等の金属アルコキシド類等である。 塩 基 The base used in the present reaction is an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate or tripotassium phosphate, or a metal alkoxide such as sodium methoxide, sodium ethoxide or potassium @ t-butoxide.
　本反応に使用する塩基の量は、式（１ａ－ｂ）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上５０当量以下である。 The amount of the base used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1a-b), but is preferably 1 to 50 equivalents.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、水溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but an aqueous solvent, an ether such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc. Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１ａ－ｂ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 times or more and 200 times or more the compound represented by the formula (1a-b). It is as follows.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、３０℃以上２００℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 30 ° C or more and 200 ° C or less or the boiling point of the solvent or less.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。また、濾過操作を行うことにより、不溶物を除去することも可能であるが必須ではない。 の 後 As the post-treatment of the reaction, liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. It is also possible, but not essential, to remove insolubles by performing a filtration operation.
　前記で得られた式（１ａ－ｄ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (1a-d) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（１ａ－ｄ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by the formula (1a-d) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（１ａ－ｄ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by the formula (1a-d) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
［製造方法Ｉ］
Figure JPOXMLDOC01-appb-C000066
 [Manufacturing method I]
Figure JPOXMLDOC01-appb-C000066
　式中、Ｒ５ｅは置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５ｂ、ＸおよびＹは前記と同義である。 In the formula, R5e represents a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with the substituent A, and R1, R2, R3, R4, R5b, X and Y are as defined above. It is.
　製造方法Ｉは、式（１ａ）で表される化合物のうち、Ｒ５ｅが置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基である式（１ａ－ｅ）で表される化合物の合成方法であって、（１ａ－ｂ）で表される化合物と末端アルキン化合物とを遷移金属類および塩基の存在下で反応させる薗頭カップリングによって得ることを含む製造方法である。 In the production method I, among the compounds represented by the formula (1a), R5e is a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with a substituent A. e) a method for synthesizing a compound represented by (e), comprising obtaining the compound represented by (1a-b) and a terminal alkyne compound by Sonogashira coupling in the presence of a transition metal and a base. It is a manufacturing method.
　式（１ａ－ｂ）中、好ましいＲ５ｂは、塩素原子、臭素原子、またはヨウ素原子である。 好 ま し い In the formula (1a-b), preferred R5b is a chlorine atom, a bromine atom, or an iodine atom.
　本反応に使用する末端アルキン化合物は、市販品として入手または公知の方法で製造することができる。また、末端アルキン化合物として、トリメチルシリルアセチレンも使用することができる。この場合は、式（１ａ－ｂ）で表される化合物にトリメチルシリルエチニル基を導入後、脱シリル化を行う必要がある。脱シリル化については、ジャーナル　オブ　ザ　アメリカン　ケミカル　ソサエティー（Ｊｏｕｒｎａｌ　ｏｆ　ｔｈｅ　Ａｍｅｒｉｃａｎ　Ｃｈｅｍｉｃａｌ　Ｓｏｃｉｅｔｙ）、第１３１巻、２号、６３４－６４３頁（２００９）．およびジャーナル　オブ　オルガノメタリック　ケミストリー（Ｊｏｕｒｎａｌ　ｏｆ　Ｏｒｇａｎｏｍｅｔａｌｌｉｃ　Ｃｈｅｍｉｓｔｒｙ）、６９６巻、２５号、４０３９－４０４５頁（２０１１）．等の非特許文献を参考にして行うことができる。 末端 The terminal alkyne compound used in this reaction can be obtained as a commercial product or can be produced by a known method. Further, trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to introduce a trimethylsilylethynyl group into the compound represented by the formula (1a-b) and then perform desilylation. Regarding desilylation, see Journal of the American Chemical Society, vol. 131, No. 2, pp. 634-643 (2009), Journal of the American Chemical Society. And Journal of Organometallic Chemistry, 696, 25, pp. 4039-4045 (2011). And the like.
　本反応に使用する末端アルキン化合物の量は、式（１ａ－ｂ）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of the terminal alkyne compound used in this reaction is not particularly limited as long as the intended reaction proceeds, provided that the amount of the terminal alkyne compound is at least 1 equivalent to the compound represented by the formula (1a-b). Preferably, it is 1 equivalent or more and 10 equivalents or less.
　本反応に使用する遷移金属類は、配位子を有してよく、酢酸パラジウム、［１，１’－ビス（ジフェニルホスフィノ）フェロセン］パラジウムジクロリド、トリス(ジベンジリデンアセトン)ジパラジウム、テトラキス（トリフェニルホスフィン）パラジウム、ビス（トリフェニルホスフィン）パラジウムジクロリド等のパラジウム類等である。また、塩化銅、臭化銅、ヨウ化銅等の銅類も同時に使用する。 The transition metals used in this reaction may have a ligand and include palladium acetate, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, tris (dibenzylideneacetone) dipalladium, tetrakis ( And palladiums such as triphenylphosphine) palladium and bis (triphenylphosphine) palladium dichloride. In addition, coppers such as copper chloride, copper bromide, and copper iodide are used at the same time.
　本反応に使用する遷移金属類の量は、パラジウム類等および銅類が、それぞれ式（１ａ－ｂ）で表される化合物に対して０．００１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはない。好ましい量は、双方ともに０．００１当量以上１当量以下である。 The amount of the transition metal used in this reaction may be at least 0.001 equivalent of the palladium or the like and the copper to the compound represented by the formula (1a-b), respectively. There is no particular limitation as long as it is done. Preferred amounts are 0.001 equivalent to 1 equivalent in both cases.
　本反応に使用する塩基は、トリエチルアミン、トリブチルアミン、イソプロピルアミン、ジエチルアミン、ジイソプロピルアミン、ジイソプロピルエチルアミン等の有機アミン類や、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等の無機塩基類等が挙げられる。 塩 基 Examples of the base used in the present reaction include organic amines such as triethylamine, tributylamine, isopropylamine, diethylamine, diisopropylamine and diisopropylethylamine, and inorganic bases such as sodium carbonate, potassium carbonate and cesium carbonate.
　本反応に使用する塩基の量は、式（１ａ－ｂ）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上５０当量以下である。また、有機塩基で液体状のものに関しては、溶媒として使用することができる。 The amount of the base used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (1a-b), but is preferably 1 to 50 equivalents. In addition, an organic base in a liquid state can be used as a solvent.
　本反応を効率的に進行させるために、トリｔ－ブチルホスフィン、２－ジシクロヘキシルホスフィノ－２’４’６’－トリイソプロピルビフェニル等のホスフィン配位子を添加することができるが、必須ではない。 A phosphine ligand such as tri-t-butylphosphine or 2-dicyclohexylphosphino-2′4′6′-triisopropylbiphenyl can be added for efficient progress of the reaction, but is not essential. .
　本反応に使用するホスフィン配位子の量は、式（１ａ－ｂ）で表される化合物に対して０．００１当量以上１当量以下であるが、目的とする反応が進行する限りにおいて特に限定されることはない。 The amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less based on the compound represented by the formula (1a-b), but is not particularly limited as long as the desired reaction proceeds. It will not be done.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、トリエチルアミン、トリブチルアミン、イソプロピルアミン、ジエチルアミン、ジイソプロピルアミン、ジイソプロピルエチルアミン等の有機アミン溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N, N-dimethylformamide Solvents such as amide solvents such as N, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, triethylamine, Butylamine, isopropylamine, diethylamine, diisopropylamine, organic amine solvents such as diisopropylethylamine. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１ａ－ｂ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 times or more and 200 times or more the compound represented by the formula (1a-b). It is as follows.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１５０℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 0 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。また、濾過操作を行うことにより、不溶物を除去することも可能であるが必須ではない。 の 後 As the post-treatment of the reaction, liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield. It is also possible, but not essential, to remove insolubles by performing a filtration operation.
　前記で得られた式（１ａ－ｅ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (1a-e) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（１ａ－ｅ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 反 応 The reaction mixture containing the compound represented by the formula (1a-e) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（１ａ－ｅ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by the formula (1a-e) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
［製造方法Ｊ］
Figure JPOXMLDOC01-appb-C000067
 [Production method J]
Figure JPOXMLDOC01-appb-C000067
　式中、ＲｙａはＣ１～Ｃ６のアルコキシ基を表し、Ｙａは、チオフェン－２－イル基、またはチオフェン－３－イル基を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｘおよび破線部は前記と同義である。 In the formula, Rya represents a C1 to C6 alkoxy group, Ya represents a thiophen-2-yl group or a thiophen-3-yl group, and R1, R2, R3, R4, R5, X and the dashed line represent Is synonymous with
　製造方法Ｊは、式（１）で表される化合物のうち、水酸基を有する式（１－ｂ）で表される化合物の合成方法であって、ＲｙａがＣ１～Ｃ６のアルコキシ基である式（１－ａ）で表される化合物と酸とを反応させることによって得ることを含む製造方法である。 Production method J is a method for synthesizing a compound represented by the formula (1-b) having a hydroxyl group among the compounds represented by the formula (1), wherein Rya is a C1-C6 alkoxy group. This is a production method including obtaining the compound represented by 1-a) by reacting the compound with an acid.
　本反応に使用する酸として、三塩化ホウ素、三臭化ホウ素等のハロゲン化ホウ素類等がある。 酸 Examples of the acid used in the reaction include boron halides such as boron trichloride and boron tribromide.
　本反応に使用する酸の量は、式（１－ａ）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。 The amount of the acid used in this reaction may be at least 1 equivalent to the compound represented by the formula (1-a), and is not particularly limited as long as the desired reaction proceeds, but is preferably Is 1 equivalent or more and 10 equivalents or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、アセトニトリル等のニトリル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, and nitrile solvents such as acetonitrile. Halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１－ａ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 times or more and 200 times or more the weight of the compound represented by the formula (1-a). It is as follows.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－８０℃以上１００℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually −80 ° C. or more and 100 ° C. or less or the boiling point of the solvent or less.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 の 後 As the post-treatment of the reaction, liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
　前記で得られた式（１－ｂ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (1-b) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（１－ｂ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 溶媒 From the reaction mixture containing the compound represented by the formula (1-b) obtained above, the solvent can be distilled off under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（１－ｂ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by the formula (1-b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
［製造方法Ｋ］
Figure JPOXMLDOC01-appb-C000068
 [Manufacturing method K]
Figure JPOXMLDOC01-appb-C000068
　式中、Ｒｙｂは、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニル基、Ｃ３～Ｃ６のハロアルキニル基、置換基Ｄで適宜０～５置換されてもよいアリール基、置換基Ｄで適宜０～２置換されてもよいヘテロアリール基、置換基Ｄで適宜０～５置換されてもよいアラルキル基、またはＲｘ１Ｃ（＝Ｏ）－を表し、Ｌｖ、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒｘ１、Ｘ、Ｙａおよび破線部は前記と同義である。 In the formula, Ryb is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent A C2-C6 alkenyl group optionally substituted with C, a C2-C6 haloalkenyl group, a C3-C6 alkynyl group optionally substituted with a substituent C, a C3-C6 haloalkynyl group, a substituent An aryl group optionally substituted with 0 to 5 substituents D, a heteroaryl group optionally substituted with 0 to 2 substituents D, an aralkyl group optionally substituted with 0 to 5 substituents D, or Rx1C ( ＯO)-, and Lv, R1, R2, R3, R4, R5, Rx1, X, Ya and the broken line have the same meanings as above.
　製造方法Ｋは、式（１）で表される化合物のうち、Ｒｙｂが置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニル基、Ｃ３～Ｃ６のハロアルキニル基、置換基Ｄで適宜０～５置換されてもよいアリール基、置換基Ｄで適宜０～２置換されてもよいヘテロアリール基、置換基Ｄで適宜０～５置換されてもよいアラルキル基、またはＲｘ１Ｃ（＝Ｏ）－（Ｒｘ１は、前記と同義である。）を表す式（１－ｃ）で表される化合物の合成方法であって、式（１－ｂ）で表される化合物とＲｙｂ－Ｌｖとを、塩基存在下、溶媒中で反応させることを含む製造方法である。 In the production method K, among the compounds represented by the formula (1), Ryb is optionally substituted with a C1 to C6 alkyl group, a C1 to C6 haloalkyl group or a substituent C, which may be appropriately substituted with a substituent C. A C3-C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent C, a C2-C6 haloalkenyl group, a C3-C6 optionally substituted with a substituent C An alkynyl group, a C3 to C6 haloalkynyl group, an aryl group optionally substituted with 0 to 5 substituents D, a heteroaryl group optionally substituted with 0 to 2 substituents D, and 0 optional substituent D A method for synthesizing an aralkyl group which may be substituted by 5 to 5 or a compound represented by formula (1-c) representing Rx1C (＝ O)-(Rx1 has the same meaning as described above), The compound represented by 1-b) and Ry And -lv, the presence of a base, a production method comprising reacting in a solvent.
　本反応に使用するＲｙｂ－Ｌｖは、市販品として入手または公知の方法で製造することができる。 ＲRyb-Lv used in this reaction can be obtained as a commercial product or can be produced by a known method.
　本反応に使用するＲｙｂ－Ｌｖは、式（１－ｂ）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。 Ryb-Lv used in this reaction may be at least 1 equivalent to the compound represented by the formula (1-b), and is not particularly limited as long as the desired reaction proceeds, but is preferably used. Is 1 equivalent or more and 10 equivalents or less.
　本反応に使用する塩基として、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、水素化ナトリウム等の無機塩基類や、トリエチルアミン、トリブチルアミン、ジイソプロピルエチルアミン、ピリジン、４－ジメチルアミノピリジン、コリジン、ルチジン等の有機塩基類が例示されるが、目的とする反応が進行する限りにおいて特に限定されることはない。 Examples of the base used in this reaction include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and sodium hydride, and organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine and lutidine. However, there is no particular limitation as long as the desired reaction proceeds.
　本反応に使用する塩基は、式（１－ｂ）で表される化合物に対して１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上１０当量以下である。 The base used in this reaction may be at least 1 equivalent to the compound represented by the formula (1-b), and is not particularly limited as long as the desired reaction proceeds. It is 1 equivalent or more and 10 equivalents or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ジメチルスルホキシド、スルホラン等の硫黄系溶媒、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; Alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; Amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, Chloroform, halogenated solvents such as carbon tetrachloride, dimethyl sulfoxide, sulfur-based solvents such as sulfolane, acetone, methyl ethyl ketone, ketone solvents such as methyl isobutyl ketone. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１－ｂ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually at least 3 times by weight to 200 times by weight the compound represented by the formula (1-b). It is as follows.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－２０℃以上１５０℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually -20 ° C or more and 150 ° C or less or the boiling point of the solvent or less.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 の 後 As the post-treatment of the reaction, liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
　前記で得られた式（１－ｃ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (1-c) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（１－ｃ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 溶媒 From the reaction mixture containing the compound represented by the formula (1-c) obtained above, the solvent can be distilled off under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（１－ｃ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by the formula (1-c) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
［製造方法Ｌ］
Figure JPOXMLDOC01-appb-C000069
 [Manufacturing method L]
Figure JPOXMLDOC01-appb-C000069
　式中、Ｒｘａは、水素原子、ハロゲン原子、シアノ基、ニトロ基、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２およびＲｘ３は、前記と同義である。）を表し、ｎａは１～２の整数を表し（ただし、ｎａ＝２の場合、２のＲｘａは、それぞれ独立した置換基を表す。）、Ｒ１、Ｒ５、Ｒｙａ、Ｘ、Ｙおよび破線部は前記と同義である。ただし、式（１－ｄ）および式（１－ｅ）で表される化合物中のＲｘａ、式（１－ｄ）で表される化合物中のＲｙａならびに式（１－ｅ）で表される化合物中の水酸基は、式（１）で表される化合物中のＲ２、Ｒ３またはＲ４に該当するいずれかの位置に置換する。 In the formula, Rxa is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, and a substituent C C3-C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 alkynyl optionally substituted with substituent C A group, a C2 to C6 haloalkynyl group, Rc-L- (where Rc and L are as defined above), RaRbN- (where Ra and Rb are as defined above), Or Rx2C (= O) N (Rx3)-(where Rx2 and Rx3 have the same meanings as described above), and na represents an integer of 1 to 2 (however, when na = 2, Rxa is German .) Representing the the substituents, R1, R5, Rya, X, Y and the broken line portion are as defined above. However, Rxa in the compound represented by the formula (1-d) and the formula (1-e), Rya in the compound represented by the formula (1-d), and the compound represented by the formula (1-e) The hydroxyl group in the formula (1) is substituted at any position corresponding to R2, R3 or R4 in the compound represented by the formula (1).
　製造方法Ｌは、式（１）で表される化合物のうち、水酸基を有する式（１－ｅ）で表される化合物の合成方法であって、式（１－ｄ）で表される化合物と酸とを反応させることによって得ることを含む製造方法である。 The production method L is a method for synthesizing a compound represented by the formula (1-e) having a hydroxyl group among the compounds represented by the formula (1), wherein the compound represented by the formula (1-d) It is a production method including obtaining by reacting with an acid.
　製造方法Ｊにおける式（１－ａ）で表される化合物を、式（１－ｄ）で表される化合物に代えて使用することにより、製造方法Ｊに準じて製造方法Ｌを実施することができる。 By using the compound represented by formula (1-a) in production method J instead of the compound represented by formula (1-d), production method L can be carried out according to production method J. it can.
［製造方法Ｍ］
Figure JPOXMLDOC01-appb-C000070
 [Manufacturing method M]
Figure JPOXMLDOC01-appb-C000070
　式中、Ｌｖ、Ｒ１、Ｒ５、Ｒｘａ、Ｒｙｂ、Ｘ、Ｙ、ｎａおよび破線部は前記と同義である。ただし、式（１－ｅ）および式（１－ｆ）で表される化合物中のＲｘａ、式（１－ｅ）で表される化合物中の水酸基ならびに式（１－ｆ）で表される化合物中のＲｙｂ－Ｏ－は、式（１）で表される化合物中のＲ２、Ｒ３またはＲ４に該当するいずれかの位置に置換する。また、ｎａ＝２の場合、２のＲｘａは、それぞれ独立した置換基を表す。 中 In the formula, Lv, R1, R5, Rxa, Ryb, X, Y, na and the broken line have the same meaning as described above. However, Rxa in the compound represented by the formula (1-e) and the formula (1-f), the hydroxyl group in the compound represented by the formula (1-e), and the compound represented by the formula (1-f) Ryb-O- in the formula is substituted at any position corresponding to R2, R3 or R4 in the compound represented by the formula (1). Further, when na = 2, Rxa of 2 represents an independent substituent.
　製造方法Ｍは、式（１）で表される化合物のうち、式（１－ｆ）で表される化合物の合成方法であって、式（１－ｅ）で表される化合物とＲｙｂ－Ｌｖとを、塩基存在下、溶媒中で反応させることを含む製造方法である。 The production method M is a method for synthesizing the compound represented by the formula (1-f) among the compounds represented by the formula (1), wherein the compound represented by the formula (1-e) and Ryb-Lv And a reaction in the presence of a base in a solvent.
　製造方法Ｋにおける式（１－ｂ）で表される化合物を、式（１－ｅ）で表される化合物に代えて使用することにより、製造方法Ｋに準じて製造方法Ｍを実施することができる。 By using the compound represented by the formula (1-b) in the production method K instead of the compound represented by the formula (1-e), the production method M can be carried out according to the production method K. it can.
［製造方法Ｎ］
Figure JPOXMLDOC01-appb-C000071
 [Manufacturing method N]
Figure JPOXMLDOC01-appb-C000071
　式中、Ｒｙｃはハロゲン原子を表し、Ｙｂは、チオフェン－２－イル基、またはチオフェン－３－イル基を表し、Ｒｙｄは置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、またはＣ２～Ｃ６のハロアルケニル基を表し、Ｒｙｄ－Ｂは有機ボロン酸類を表し、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｘおよび破線部は前記と同義である。 In the formula, Ryc represents a halogen atom, Yb represents a thiophen-2-yl group or a thiophen-3-yl group, and Ryd represents a C1-C6 alkyl group optionally substituted with a substituent C; A C 6 -C 6 haloalkyl group, a C 3 -C 8 cycloalkyl group optionally substituted with a substituent C, a C 2 -C 6 alkenyl group optionally substituted with a substituent C, or a C 2 -C 6 haloalkenyl group. In the formula, Ryd-B represents an organic boronic acid, and R1, R2, R3, R4, R5, X and the broken line have the same meanings as described above.
　製造方法Ｎは、式（１）で表される化合物のうち、Ｒｙｄが置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、またはＣ２～Ｃ６のハロアルケニル基である式（１－ｈ）で表される化合物の合成方法であって、式（１－ｇ）で表される化合物と有機ボロン酸類（Ｒｙｄ－Ｂ）とを反応させる鈴木－宮浦カップリングによって得ることを含む製造方法である。 In the production method N, among the compounds represented by the formula (1), Ryd is appropriately substituted with a C1 to C6 alkyl group, a C1 to C6 haloalkyl group or a substituent C, which may be appropriately substituted with a substituent C. A C3-C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent C, or a C2-C6 haloalkenyl group represented by the formula (1-h): This is a synthesis method, which comprises obtaining the compound represented by the formula (1-g) by Suzuki-Miyaura coupling with an organic boronic acid (Ryd-B).
　式（１－ｇ）で表される化合物中、好ましいＲｙｃは、塩素原子、臭素原子、またはヨウ素原子である。 中 In the compound represented by the formula (1-g), preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
　本反応に使用するＲｙｄ－Ｂは、有機ボロン酸や有機ボロン酸エステル等の有機ボロン酸類を表し、市販品として入手または公知の方法で製造できる。 Ryd-B used in this reaction represents an organic boronic acid such as an organic boronic acid or an organic boronic ester, and can be obtained as a commercial product or can be produced by a known method.
　製造方法Ｈにおける式（１ａ－ｂ）で表される化合物とＲ５ｄ－Ｂとを、それぞれ式（１－ｇ）で表される化合物とＲｙｄ－Ｂとに代えて使用することにより、製造方法Ｈに準じて製造方法Ｎを実施することができる。 By using the compound represented by the formula (1a-b) and R5d-B in the production method H in place of the compound represented by the formula (1-g) and Ryd-B, respectively, the production method H The manufacturing method N can be performed according to
［製造方法Ｏ］
Figure JPOXMLDOC01-appb-C000072
 [Production method O]
Figure JPOXMLDOC01-appb-C000072
　式中、Ｒｘｂは、水素原子、シアノ基、ニトロ基、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、Ｃ２～Ｃ６のハロアルケニル基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、Ｃ２～Ｃ６のハロアルキニル基、置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、Ｃ２～Ｃ６のハロアルケニルオキシ基、置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、Ｃ３～Ｃ６のハロアルキニルオキシ基、置換基Ｄで適宜０～５置換されてもよいアリールオキシ基、置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基、置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、前記と同義である。）、Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、前記と同義である。）、１～２個の酸素原子を含む３～６員環の基、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２およびＲｘ３は、前記と同義である。）を表し、Ｒｙｃ、Ｒｙｄ、Ｒｙｄ－Ｂ、Ｒ１、Ｒ５、Ｘ、Ｙ、ｎａおよび破線部は前記と同義である。ただし、式（１－ｉ）および式（１－ｊ）で表される化合物中のＲｘｂ、式（１－ｉ）で表される化合物中のＲｙｃおよび式（１－ｊ）で表される化合物中のＲｙｄは、式（１）で表される化合物中のＲ２、Ｒ３またはＲ４に該当するいずれかの位置に置換する。また、ｎａ＝２の場合、２のＲｘｂは、それぞれ独立した置換基を表す。 In the formula, Rxb is a hydrogen atom, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, or a C3 optionally substituted with a substituent C. C8-C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2 A C1 to C6 haloalkynyl group optionally substituted with a substituent C, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group optionally substituted with a substituent C, A C2-C6 alkenyloxy group optionally substituted with a substituent C, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy optionally substituted with a substituent C , A C3-C6 haloalkynyloxy group, an aryloxy group optionally substituted with 0 to 5 substituents D, a heteroaryloxy group optionally substituted with 0 to 2 substituents D, and an appropriate substituent D An aralkyloxy group which may be substituted with 0 to 5, Rx1C (= O)-(where Rx1 has the same meaning as described above), and Rx1C (= O) O- (where Rx1 has the same meaning as described above) ), A 3- to 6-membered ring group containing 1 or 2 oxygen atoms, Rc-L- (where Rc and L are as defined above), RaRbN- (where Ra is the same as above). And Rb are as defined above, or Rx2C (= O) N (Rx3)-(where Rx2 and Rx3 are as defined above), and Ryc, Ryd, Ryd-B, R1, R5, X, Y, na and the broken line part are as defined above. That. However, Rxb in the compound represented by the formula (1-i) and the formula (1-j), Ryc in the compound represented by the formula (1-i), and the compound represented by the formula (1-j) Ryd in the formula (1) is substituted at any position corresponding to R2, R3 or R4 in the compound represented by the formula (1). Further, when na = 2, Rxb of 2 represents an independent substituent.
　製造方法Ｏは、式（１）で表される化合物のうち、式（１－ｊ）で表される化合物の合成方法であって、式（１－ｉ）で表される化合物と有機ボロン酸類（Ｒｙｄ－Ｂ）とを反応させる鈴木－宮浦カップリングによって得ることを含む製造方法である。 Production method O is a method for synthesizing the compound represented by the formula (1-j) among the compounds represented by the formula (1), wherein the compound represented by the formula (1-i) and the organic boronic acid (Ryd-B) to obtain a Suzuki-Miyaura coupling.
　式（１－ｉ）で表される化合物中、好ましいＲｙｃは、塩素原子、臭素原子、またはヨウ素原子である。 中 In the compound represented by the formula (1-i), preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
　製造方法Ｈにおける式（１ａ－ｂ）で表される化合物とＲ５ｄ－Ｂとを、それぞれ式（１－ｉ）で表される化合物とＲｙｄ－Ｂとに代えて使用することにより、製造方法Ｈに準じて製造方法Ｏを実施することができる。 By using the compound represented by the formula (1a-b) and R5d-B in the production method H in place of the compound represented by the formula (1-i) and Ryd-B, respectively, the production method H The manufacturing method O can be performed according to
［製造方法Ｐ］
Figure JPOXMLDOC01-appb-C000073
 [Manufacturing method P]
Figure JPOXMLDOC01-appb-C000073
　式中、Ｒｙｅは置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基を表し、Ｒｙｃ、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｘ、Ｙｂおよび破線部は前記と同義である。 In the formula, Rye represents a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with a substituent C, and Ryc, R1, R2, R3, R4, R5, X, Yb and a broken line The parts are as defined above.
　製造方法Ｐは、式（１）で表される化合物のうち、Ｒｙｅが置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、またはＣ２～Ｃ６のハロアルキニル基である式（１－ｋ）で表される化合物の合成方法であって、式（１－ｇ）で表される化合物と末端アルキン化合物とを反応させる薗頭カップリングによって得ることを含む製造方法である。 In the production method P, among the compounds represented by the formula (1), Rye is a C2-C6 alkynyl group optionally substituted with a substituent C or a C2-C6 haloalkynyl group. A method for synthesizing the compound represented by the formula (k), comprising obtaining the compound represented by the formula (1-g) by Sonogashira coupling with a terminal alkyne compound.
　式（１－ｇ）で表される化合物中、好ましいＲｙｃは、塩素原子、臭素原子、またはヨウ素原子である。 中 In the compound represented by the formula (1-g), preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
　製造方法Ｉにおける式（１ａ－ｂ）で表される化合物を式（１－ｇ）で表される化合物に代えて使用することにより、製造方法Ｉに準じて製造方法Ｐを実施することができる。 By using the compound represented by formula (1a-b) in production method I instead of the compound represented by formula (1-g), production method P can be carried out according to production method I. .
［製造方法Ｑ］
Figure JPOXMLDOC01-appb-C000074
 [Production method Q]
Figure JPOXMLDOC01-appb-C000074
　式中、Ｒｘｂ、Ｒｙｃ、Ｒｙｅ、Ｒ１、Ｒ５、Ｘ、Ｙ、ｎａおよび破線部は前記と同義である。ただし、式（１－ｉ）および式（１－ｌ）で表される化合物中のＲｘｂ、式（１－ｉ）で表される化合物中のＲｙｃおよび式（１－ｌ）で表される化合物中のＲｙｅは、式（１）で表される化合物中のＲ２、Ｒ３またはＲ４に該当するいずれかの位置に置換する。また、ｎａ＝２の場合、２のＲｘｂは、それぞれ独立した置換基を表す。 中 In the formula, Rxb, Ryc, Rye, R1, R5, X, Y, na, and the broken line have the same meanings as described above. However, Rxb in the compound represented by the formula (1-i) and the formula (1-1), Ryc in the compound represented by the formula (1-i), and the compound represented by the formula (1-1) Rye in the formula (1) is substituted at any position corresponding to R2, R3 or R4 in the compound represented by the formula (1). Further, when na = 2, Rxb of 2 represents an independent substituent.
　製造方法Ｐは、式（１）で表される化合物のうち、式（１－ｌ）で表される化合物の合成方法であって、式（１－ｉ）で表される化合物と末端アルキン化合物とを反応させる薗頭カップリングによって得ることを含む製造方法である。 The production method P is a method for synthesizing a compound represented by the formula (1-1) among the compounds represented by the formula (1), wherein the compound represented by the formula (1-i) and a terminal alkyne compound And Sonogashira coupling.
　式（１－ｉ）で表される化合物中、好ましいＲｙｃは、塩素原子、臭素原子、またはヨウ素原子である。 中 In the compound represented by the formula (1-i), preferred Ryc is a chlorine atom, a bromine atom, or an iodine atom.
　製造方法Ｉにおける式（１ａ－ｂ）で表される化合物を式（１－ｉ）で表される化合物に代えて使用することにより、製造方法Ｉに準じて製造方法Ｑを実施することができる。 By using the compound represented by the formula (1a-b) in the production method I instead of the compound represented by the formula (1-i), the production method Q can be carried out according to the production method I. .
［製造方法Ｒ］
Figure JPOXMLDOC01-appb-C000075
 [Production method R]
Figure JPOXMLDOC01-appb-C000075
　式中、ＬａはＳを表し、ＬｂはＳＯまたはＳＯ２を表し、Ｏｘ’は酸化剤を表す。 In the formula, La represents S, Lb represents SO or SO 2 , and Ox ′ represents an oxidizing agent.
　製造方法Ｒは、式（１）で表される化合物中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、およびＲ６に含まれるＬｂがＳＯまたはＳＯ２である式（Ｌｂ）で表される化合物の製造方法であって、式（１）で表される化合物中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、およびＲ６に含まれるＬａがＳである式（Ｌａ）で表される化合物と酸化剤（Ｏｘ’）とを、溶媒中で反応させることを含む製造方法である。 Production method R is in the compounds of formula (1), manufacture of R1, R2, R3, R4, R5, and Lb contained in R6 is represented by the formula (Lb) is SO or SO 2 Compound A method according to claim 1, wherein in the compound represented by the formula (1), the compound represented by the formula (La) wherein La contained in R1, R2, R3, R4, R5, and R6 is S, and an oxidizing agent (Ox ') In a solvent.
　本反応に使用する酸化剤は、過酸化水素水、メタ－クロロ過安息香酸等の過酸化物類等が挙げられる。また、タングステン酸ナトリウムのような遷移金属類を添加することもできる。 酸化 Examples of the oxidizing agent used in the present reaction include peroxides such as aqueous hydrogen peroxide and meta-chloroperbenzoic acid. Also, transition metals such as sodium tungstate can be added.
　本反応に使用する酸化剤の量は、ＳＯを製造する際には式（Ｌａ）で表される化合物に対して、通常、１．０当量以上１．２当量以下であり、ＳＯ２を製造する際には、通常、２当量以上１０当量以下である。また、遷移金属類を添加する際には、通常、０．００１当量以上１当量以下である。 The amount of oxidizing agent used in this reaction, to the compound represented by the formula (La) in the manufacture of SO, is usually, 1.0 1.2 equivalents or less equivalent or more, producing SO 2 In doing so, it is usually 2 equivalents or more and 10 equivalents or less. In addition, when a transition metal is added, it is usually 0.001 equivalent or more and 1 equivalent or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、水溶媒、酢酸等の酸性系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、アセトニトリル等のニトリル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is not limited to an aqueous solvent, an acidic solvent such as acetic acid, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and the like. Examples thereof include benzene solvents, nitrile solvents such as acetonitrile, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（Ｌａ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (La). is there.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－１０℃以上１２０℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually -10 ° C or more and 120 ° C or less or the boiling point of the solvent or less.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 の 後 As the post-treatment of the reaction, liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, thiosulfate An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be used arbitrarily. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
　前記で得られた式（Ｌｂ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (Lb) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（Ｌｂ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by the formula (Lb) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（Ｌｂ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by formula (Lb) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
［製造方法Ｓ］
Figure JPOXMLDOC01-appb-C000076
 [Manufacturing method S]
Figure JPOXMLDOC01-appb-C000076
　式中、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ８、ＸおよびＹは、前記と同義である。 中 In the formula, R2, R3, R4, R5, R8, X and Y are as defined above.
　製造方法Ｓは、式（３）で表される製造中間体の製造方法であって、式（５）で表される化合物と式（６）で表される化合物とを、塩基存在下溶媒中で反応させることを含む製造方法である。 The production method S is a method for producing a production intermediate represented by the formula (3), in which a compound represented by the formula (5) and a compound represented by the formula (6) are dissolved in a solvent in the presence of a base. And a reaction method comprising reacting
　本反応に使用する式（５）で表される化合物は、参考例に準じて合成することができる。また、グリーン　ケミストリー（Ｇｒｅｅｎ　Ｃｈｅｍｉｓｔｒｙ）、第４１巻、５８０－５８５頁や、ザ　ジャーナル　オブ　オルガニック　ケミストリー（Ｔｈｅ　Ｊｏｕｒｎａｌ　ｏｆ　Ｏｒｇａｎｉｃ　Ｃｈｅｍｉｓｔｒｙ）、第６５巻、２０号、６４５８－６４６１頁（２０００）．等を参照にしても合成することができる。 化合物 The compound represented by the formula (5) used in this reaction can be synthesized according to Reference Examples. Also, Green Chemistry, Vol. 41, pp. 580-585, and The Journal of Organic Chemistry, Vol. 65, No. 6, pp. 6458-6461 (2000). Can be synthesized by referring to the above.
　本反応に使用する式（６）で表される化合物は、市販品として入手または公知の方法で製造できることができる。 化合物 The compound represented by the formula (6) used in this reaction can be obtained as a commercial product or can be produced by a known method.
　本反応に使用する式（６）で表される化合物の量は、式（５）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは１当量以上３当量以下である。 The amount of the compound represented by the formula (6) used in this reaction is not particularly limited as long as the target reaction proceeds as long as the amount of the compound represented by the formula (5) is 1 equivalent or more. But not more than 1 equivalent and not more than 3 equivalents.
　本反応に使用する塩基は、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、リン酸三カリウムのような無機塩基類やナトリウムメトキシド、ナトリウムエトキシド、カリウム　ｔ－ブトキシド等の金属アルコキシド類等である。 塩 基 The base used in the present reaction is an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate or tripotassium phosphate, or a metal alkoxide such as sodium methoxide, sodium ethoxide or potassium @ t-butoxide.
　本反応に使用する塩基は、触媒量で実施することが可能であり、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、式（５）で表される化合物に対して０．０１当量以上３当量以下である。 The base used in this reaction can be carried out in a catalytic amount, and is not particularly limited as long as the desired reaction proceeds, but is preferably a compound represented by the formula (5). On the other hand, it is 0.01 to 3 equivalents.
　本反応に使用する溶媒は、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ジメチルスルホキシド、スルホラン等の硫黄系溶媒、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 Solvents used in this reaction include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; Ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate; nitrile solvents such as acetonitrile; amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide and N, N-dimethylacetamide; 1,3-dimethyl Urea solvents such as -2-imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride; sulfur solvents such as dimethyl sulfoxide and sulfolane; acetone, methyl ethyl ketone and methyl Ketone solvents such as Sobuchiruketon like. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（５）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (5). is there.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－５０℃以上１５０℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually -50 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 の 後 As the post-treatment of the reaction, liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
　前記で得られた式（３）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (3) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（３）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 The reaction mixture containing the compound represented by the formula (3) obtained above can be distilled under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（３）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by the formula (3) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
［製造方法Ｔ］
Figure JPOXMLDOC01-appb-C000077
 [Manufacturing method T]
Figure JPOXMLDOC01-appb-C000077
　式中、Ｒ８ａはＣ１～Ｃ６のアルキル基を表し、Ｒ２、Ｒ３、Ｒ４、Ｒ５、ＸおよびＹは、前記と同義である。 In the formula, R8a represents a C1 to C6 alkyl group, and R2, R3, R4, R5, X and Y are as defined above.
　製造方法Ｔは、式（３）で表される化合物のうち、式（３ｂ）で表される製造中間体の製造方法であって、式（３ａ）で表される化合物を、酸性条件または塩基性条件下、溶媒中で反応させることを含む製造方法である。 The production method T is a method for producing a production intermediate represented by the formula (3b) among the compounds represented by the formula (3), wherein the compound represented by the formula (3a) is prepared under an acidic condition or a base condition. This is a production method comprising reacting in a solvent under ionic conditions.
　まず、酸性条件の反応について説明する。 First, the reaction under acidic conditions will be described.
　本反応に使用する酸は、塩酸、臭化水素酸、リン酸等の無機酸類や、酢酸、メタンスルホン酸、ｐ－トルエンスルホン酸、トリフルオロ酢酸等の有機酸類が例示される。目的とする反応が進行する限り特に制限されることはない。 酸 Examples of the acid used in the present reaction include inorganic acids such as hydrochloric acid, hydrobromic acid and phosphoric acid, and organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid and trifluoroacetic acid. There is no particular limitation as long as the desired reaction proceeds.
　本反応に使用する酸の量は、触媒量でもよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、式（３ａ）で表される化合物に対して０．０１当量以上である。また、液体状の酸に関しては溶媒として使用することも可能である。 The amount of the acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the desired reaction proceeds, but is preferably 0.1 to 0.1 with respect to the compound represented by the formula (3a). It is at least 01 equivalent. Further, a liquid acid can be used as a solvent.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、水溶媒、酢酸、メタンスルホン酸等の酸性系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds. However, aqueous solvents, acidic solvents such as acetic acid and methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t- Ether solvents such as butyl ether, dimethoxyethane, tetrahydrofuran and dioxane; alcohol solvents such as methanol, ethanol and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene; ethyl acetate, isopropyl acetate and acetic acid Ester solvents such as butyl, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone No A solvent, dichloromethane, dichloroethane, chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（３ａ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (3a). is there.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１８０℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 0 ° C or higher and 180 ° C or lower or the boiling point of the solvent or lower.
　次に、塩基性条件の反応について説明する。 Next, the reaction under basic conditions will be described.
　本反応に使用する塩基は、水酸化リチウム、水酸化ナトリウム、水酸化カリウム等の無機塩基類が例示されるが、目的とする反応が進行する限りにおいて特に限定されることはない。 塩 基 The base used in this reaction is exemplified by inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide, but is not particularly limited as long as the desired reaction proceeds.
　本反応に使用する塩基は、式（３ａ）で表される化合物に対して１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上３０当量以下である。 The base used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as it is at least 1 equivalent to the compound represented by the formula (3a), but is preferably at least 1 equivalent. It is 30 equivalents or less.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、水溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル、ジメトキシエタン、テトラヒドロフラン、ジオキサン等のエーテル系溶媒、メタノール、エタノール、イソプロパノール等のアルコール系溶媒、ベンゼン、トルエン、キシレン、メシチレン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、アセトニトリル等のニトリル系溶媒、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、１，３－ジメチル－２－イミダゾリジノン等のウレア系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but an aqueous solvent, ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, and dioxane Solvents, alcohol solvents such as methanol, ethanol, and isopropanol; benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; ester solvents such as ethyl acetate, isopropyl acetate, and butyl acetate; and nitriles such as acetonitrile Solvent, amide solvent such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvent such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethylene Down, chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（３ａ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 to 200 times by weight based on the compound represented by the formula (3a). is there.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、－２０℃以上１８０℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is carried out is not particularly limited as long as the desired reaction proceeds, but is usually -20 ° C or more and 180 ° C or less or the boiling point of the solvent or less.
　反応の後処理は、酸性条件での反応と塩基性条件の反応は共通の方法で行える。反応混合物に対して、水、もしくは適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 の 後 The post-treatment of the reaction can be performed by a common method for the reaction under acidic conditions and the reaction under basic conditions. Separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, or the like is dissolved, or a saline solution Etc. can be used arbitrarily. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
　前記で得られた式（３ｂ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (3b) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（３ｂ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 反 応 From the reaction mixture containing the compound represented by the formula (3b) obtained above, the solvent can be distilled off under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（３ｂ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by formula (3b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
　式（３ｂ）で表される化合物は、式（３ｂ’）
Figure JPOXMLDOC01-appb-C000078
（式中、Ｒ２、Ｒ３、Ｒ４、Ｒ５、ＸおよびＹは前記と同義である。）
で表される異性体も含む。 The compound represented by the formula (3b) has the formula (3b ′)
Figure JPOXMLDOC01-appb-C000078
(In the formula, R2, R3, R4, R5, X and Y are as defined above.)
The isomer represented by is also included.
　式（３ｂ’）で表される化合物は、式（３ｂ）で表される化合物と同様に取り扱うことが可能であり、製造方法Ａを適応することができる。また、式（３ｂ’）で表される化合物は不斉炭素を含むが、その異性体混合比は、単独でも任意の割合の混合物でもよい。さらに、式（３ｂ）で表される化合物と式（３ｂ’）で表される化合物との混合物でもよく、その異性体混合比は、単独でも任意の割合の混合物でもよい。 The compound represented by the formula (3b ') can be handled in the same manner as the compound represented by the formula (3b), and the production method A can be applied. Further, the compound represented by the formula (3b ') contains an asymmetric carbon, and the isomers may be used alone or in a mixture at an arbitrary ratio. Furthermore, a mixture of the compound represented by the formula (3b) and the compound represented by the formula (3b ′) may be used, and the mixing ratio of the isomers may be singly or a mixture having an arbitrary ratio.
[製造方法Ｕ]
Figure JPOXMLDOC01-appb-C000079
 [Production method U]
Figure JPOXMLDOC01-appb-C000079
　式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５ｂ、ＸおよびＹは前記と同義である。 中 In the formula, R1, R2, R3, R4, R5b, X and Y are as defined above.
　製造方法Ｕは、式（１ａ）で表される化合物のうち、トリフルオロメチル基を有する式（１ａ－ｆ）で表される化合物の合成方法であって、式（１ａ－ｂ）で表される化合物とジフルオロ(フルオロスルホニル)酢酸メチルとを、遷移金属類存在下で反応させることを含む製造方法である。 Production method U is a method for synthesizing a compound represented by the formula (1a-f) having a trifluoromethyl group among the compounds represented by the formula (1a), and is represented by the formula (1a-b). The method comprises reacting a compound with methyl difluoro (fluorosulfonyl) acetate in the presence of transition metals.
　式（１ａ－ｂ）で表される化合物中、好ましいＲ５ｂは、塩素原子、臭素原子、またはヨウ素原子である。 中 In the compound represented by the formula (1a-b), preferred R5b is a chlorine atom, a bromine atom, or an iodine atom.
　本反応に使用するジフルオロ(フルオロスルホニル)酢酸メチルは、市販品として入手または公知の方法で製造できる。 メ チ ル Methyl difluoro (fluorosulfonyl) acetate used in this reaction can be obtained as a commercial product or can be produced by a known method.
　本反応に使用するジフルオロ(フルオロスルホニル)酢酸メチルの量は、式（１ａ－ｂ）で表される化合物に対して、１当量以上あれば、目的とする反応が進行する限りにおいて特に限定されることはないが、好ましくは、１当量以上５０当量以下である。 The amount of methyl difluoro (fluorosulfonyl) acetate used in this reaction is not particularly limited as long as the desired reaction proceeds, as long as the amount of the compound represented by the formula (1a-b) is 1 equivalent or more. However, it is preferably 1 equivalent or more and 50 equivalents or less.
　本反応に使用する遷移金属類は、銅類等である。好ましくは、臭化銅やヨウ化銅等が挙げられる。 遷移 The transition metals used in this reaction are coppers and the like. Preferably, copper bromide, copper iodide and the like are used.
　本反応に使用する遷移金属類の量は、式（１ａ－ｂ）で表される化合物に対して、１当量以上あればよく、目的とする反応が進行する限りにおいて特に制限されることはないが、好ましくは、１当量以上５０当量以下である。 The amount of the transition metals used in this reaction may be at least 1 equivalent to the compound represented by the formula (1a-b), and is not particularly limited as long as the desired reaction proceeds. However, it is preferably 1 equivalent or more and 50 equivalents or less.
　本反応を効率的に進行させるために、エチルジイソプロピルアミンやヘキサメチルリン酸トリアミド等の添加剤を加えることことができるが必須ではない。 添加 In order to make this reaction proceed efficiently, an additive such as ethyldiisopropylamine or hexamethylphosphoric triamide can be added, but is not essential.
　本反応に使用する添加剤の量は、式（１ａ－ｂ）で表される化合物に対して５０当量以下であり、目的とする反応が進行する限りにおいて特に限定されることはない。 量 The amount of the additive used in this reaction is not more than 50 equivalents to the compound represented by the formula (1a-b), and is not particularly limited as long as the desired reaction proceeds.
　本反応に使用する溶媒は、目的とする反応が進行する限りにおいて特に限定されることはないが、Ｎ－メチルピロリドン、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等のアミド系溶媒、ジメチルスルホキシド、スルホラン等の硫黄系溶媒等が挙げられる。これらの溶媒は、単独または２種類以上を任意の割合で混合して使用することができる。 The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, Sulfur-based solvents such as dimethyl sulfoxide and sulfolane. These solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio.
　本反応に使用する溶媒量は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、式（１ａ－ｂ）で表される化合物に対して３重量倍以上２００重量倍以下である。 The amount of the solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but is usually 3 times or more and 200 times or more the compound represented by the formula (1a-b). It is as follows.
　本反応を行う際の温度は、目的とする反応が進行する限りにおいて特に限定されることはないが、通常、０℃以上１５０℃以下または溶媒の沸点以下である。 温度 The temperature at which this reaction is performed is not particularly limited as long as the desired reaction proceeds, but is usually 0 ° C or higher and 150 ° C or lower or the boiling point of the solvent or lower.
　反応の後処理としては、反応混合物に対して、水または適当な水溶液を加えることにより、分液操作を行うことが可能である。水溶液を使用する場合は、塩酸、硫酸、塩化アンモニウム等を溶解した酸性水溶液、アンモニア、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム等を溶解したアルカリ水溶液、チオ硫酸ナトリウム、亜硫酸ナトリウム等の硫黄原子を含む塩を溶解した水溶液や食塩水等を任意に使用することができる。分液操作の際に、必要に応じて、トルエン、キシレン、ベンゼン、クロロベンゼン、ジクロロベンゼン等のベンゼン系溶媒、酢酸エチル、酢酸イソプロピル、酢酸ブチル等のエステル系溶媒、ジエチルエーテル、ジイソプロピルエーテル、メチル－ｔ－ブチルエーテル等のエーテル系溶媒、ジクロロメタン、ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン系溶媒、ヘキサン、ヘプタン、シクロヘキサン、メチルシクロヘキサン等の炭化水素系溶媒等の水と相溶することのない溶媒を追加することが可能である。また、これらの溶媒は、単独で使用することも、２種類以上で任意の割合で混合することも可能である。分液の回数は特に制限されることがなく、目的とする純度や収量に応じて実施することができる。 の 後 As the post-treatment of the reaction, liquid separation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When an aqueous solution is used, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride, etc. are dissolved, an alkaline aqueous solution in which ammonia, potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, etc. are dissolved, An aqueous solution or salt solution in which a salt containing a sulfur atom such as sodium thiosulfate or sodium sulfite is dissolved can be arbitrarily used. In the separation operation, if necessary, a benzene solvent such as toluene, xylene, benzene, chlorobenzene, dichlorobenzene, an ester solvent such as ethyl acetate, isopropyl acetate, butyl acetate, diethyl ether, diisopropyl ether, methyl Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. It is possible to add. In addition, these solvents can be used alone or as a mixture of two or more kinds at an arbitrary ratio. The number of liquid separations is not particularly limited, and can be carried out according to the desired purity and yield.
　前記で得られた式（１ａ－ｆ）で表される化合物を含む反応混合物は、硫酸ナトリウムや硫酸マグネシウム等の乾燥剤で水分を除去することができるが、必須ではない。 反 応 The reaction mixture containing the compound represented by the formula (1a-f) obtained above can be removed with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.
　前記で得られた式（１ａ－ｆ）で表される化合物を含む反応混合物は、化合物が分解しない限りにおいて、減圧下で溶媒留去することが可能である。 反 応 The reaction mixture containing the compound represented by the formula (1a-f) obtained above can be evaporated under reduced pressure as long as the compound is not decomposed.
　溶媒留去後に得られた式（１ａ－ｆ）で表される化合物を含む反応混合物は、適当な溶媒により、洗浄、再沈殿、再結晶、カラムクロマトグラフィー等にて精製することができる。目的とする純度に応じて適宜設定すればよい。 反 応 The reaction mixture containing the compound represented by the formula (1a-f) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the objective purity.
　以上に示した、製造方法Ａ～製造方法Ｕを任意に組み合わせて、式（１）で表される化合物を製造することができる。もしくは、公知の方法と製造方法Ａ～製造方法Ｕを任意に組み合わせても、式（１）で表される化合物を製造することができる。 化合物 The compound represented by the formula (1) can be produced by arbitrarily combining the production methods A to U described above. Alternatively, the compound represented by the formula (1) can be produced by arbitrarily combining a known method with Production Methods A to U.
　本発明化合物は、植物に対して有害な生物を防除できるために、農薬、特に農園芸用有害生物防除剤として使用することができる。具体的には、殺菌剤、殺虫剤、除草剤、植物成長調整剤等が挙げられる。好ましくは、殺菌剤である。 化合物 Since the compound of the present invention can control harmful organisms to plants, it can be used as a pesticide, particularly a pesticide for agricultural and horticultural use. Specific examples include fungicides, insecticides, herbicides, plant growth regulators, and the like. Preferably, it is a bactericide.
　本発明化合物は、植物病害の防除のために、畑地、水田、茶園、果樹園、牧草地、芝生、森林、庭園、街路樹等で農園芸用殺菌剤として使用することができる。
　本発明でいう植物病害とは、農作物、花き、花木、樹木等の植物に萎ちょう、立枯れ、黄化、萎縮、徒長等の全身的な異常な病的症状、または斑点、葉枯れ、モザイク、葉巻、枝枯れ、根腐れ、根こぶ、こぶ等の部分的な病的症状が惹起されることである。即ち、植物が病気になることである。植物病害を引き起こす病原体として、主に、菌類、細菌、スピロプラズマ、ファイトプラズマ、ウイルス、ウイロイド、寄生性高等植物、線虫等が挙げられる。本発明化合物は菌類に有効であるが、これに限定されるものではない。 The compound of the present invention can be used as an agricultural and horticultural fungicide in fields, paddy fields, tea fields, orchards, pastures, lawns, forests, gardens, street trees, and the like for controlling plant diseases.
The plant diseases referred to in the present invention are crops, flowers, flowers, trees, trees, and other plants. , Partial pathological symptoms such as cigars, wilt, root rot, nodules, nodules and the like. That is, the plant becomes ill. Pathogens causing plant diseases mainly include fungi, bacteria, spiroplasmas, phytoplasmas, viruses, viroids, parasitic higher plants, nematodes and the like. The compound of the present invention is effective on fungi, but is not limited thereto.
　菌類によって引き起こされる病害は、主に菌類病である。菌類病を引き起こす菌類（病原体）として、ネコブカビ菌類、卵菌類、接合菌類、子のう菌類、担子菌類および不完全菌類等が挙げられる。例えば、ネコブカビ菌類として、根こぶ病菌、ジャカイモ粉状そうか病菌、テンサイそう根病菌、卵菌類として疫病菌、べと病菌、Ｐｙｔｈｉｕｍ属菌、Ａｐｈａｎｏｍｙｃｅｓ属菌、接合菌類としてＲｈｉｚｏｐｕｓ属菌、子のう菌類としてモモ縮葉病菌、トウモロコシごま葉枯病菌、イネいもち病菌、うどんこ病菌、炭そ病菌、赤かび病菌、ばか苗病菌、菌核病菌、担子菌類としてさび病菌類、黒穂病菌類、紫紋羽病菌、もち病菌、紋枯病菌、不完全菌類として灰色かび病菌、Ａｌｔｅｒｎａｒｉａ属菌、Ｆｕｓａｒｉｕｍ属菌、Ｐｅｎｉｃｉｌｌｉｕｍ属菌、Ｒｈｉｚｏｃｔｏｎｉａ属菌、白絹病菌等が挙げられる。 病 Diseases caused by fungi are mainly fungal diseases. Fungi (pathogens) which cause fungal diseases include fungus fungi, oomycetes, zygomycetes, ascomycetes, basidiomycetes and incomplete fungi. For example, as fungus fungi, root-knot fungus, powdery mildew fungus, sugar beet wilt fungus, oomycete, downy mildew, Pythium genus, Aphanomyces genus, zygomycetes Rhizopus genus, ascomycetes Fungi include peach leaf blight, corn sesame leaf blight, rice blast, powdery mildew, anthracnose, red mold, bacillus seedling, sclerotium, basidiomycetes, rust, smut, and purple print Fungi, rice blast, sheath blight, and imperfect fungi include gray mold, Alternaria, Fusarium, Penicillium, Rhizoctonia, and white silk.
　本発明化合物は、各種の植物病害に対して有効である。以下に、病害名およびその病原菌名の具体例を示す。 化合物 The compound of the present invention is effective against various plant diseases. Hereinafter, specific examples of the disease name and the pathogen name will be shown.
　イネのいもち病（Ｍａｇｎａｐｏｒｔｈｅ　ｇｒｉｓｅａ）、紋枯病（Ｔｈａｎａｔｅｐｈｏｒｕｓ　ｃｕｃｕｍｅｒｉｓ）、褐色菌核病（Ｃｅｒａｔｏｂａｓｉｄｉｕｍ　ｓｅｔａｒｉａｅ）、褐色小粒菌核病（Ｗａｉｔｅａ　ｃｉｒｃｉｎａｔａ）、褐色紋枯病（Ｔｈａｎａｔｅｐｈｏｒｕｓ　ｃｕｃｕｍｅｒｉｓ）、球状菌核病（Ｓｃｌｅｒｏｔｉｕｍ　ｈｙｄｒｏｐｈｉｌｕｍ）、赤色菌核病（Ｗａｉｒｅａ　ｃｉｒｃｉｎａｔａ）、黒しゅ病（Ｅｎｔｙｌｏｍａ　ｄａｃｔｙｌｉｄｉｓ）、小球菌核病（Ｍａｇｎａｐｏｒｔｈｅ　ｓａｌｖｉｎｉｉ）、灰色菌核病（Ｃｅｒａｔｏｂａｓｉｄｉｕｍ　ｃｏｒｎｉｇｅｒｕｍ）、ごま葉枯病（Ｃｏｃｈｌｉｏｂｏｌｕｓ　ｍｉｙａｂｅａｎｕｓ）、条葉枯病（Ｓｐｈａｅｒｕｌｉｎａ　ｏｒｙｚｉｎａ）、ばか苗病（Ｇｉｂｂｅｒｅｌｌａ　ｆｕｊｉｋｕｒｏｉ）、苗立枯病（Ｐｙｔｈｉｕｍ　ｓｐｐ．、Ｆｕｓａｒｉｕｍ　ｓｐｐ．、Ｔｒｉｃｈｏｄｅｒｍａ　ｓｐｐ．、Ｒｈｉｚｏｐｕｓ　ｓｐｐ．、Ｒｈｉｚｏｃｔｏｎｉａ　ｓｏｌａｎｉ、Ｍｕｃｏｒ　ｓｐ．、Ｐｈｏｍａ　ｓｐ．）、苗腐病（Ｐｙｔｈｉｕｍ　ｓｐｐ．、Ａｃｈｌｙａ　ｓｐｐ．、Ｄｉｃｔｙｕｃｈｕｓ　ｓｐｐ．）、稲こうじ病（Ｃｌａｖｉｃｅｐｓ　ｖｉｒｅｎｓ）、墨黒穂病（Ｔｉｌｌｅｔｉａ　ｂａｒｃｌａｙａｎａ）、褐色米（Ｃｕｒｖｕｌａｒｉａ　ｓｐｐ．、Ａｌｔｅｒｎａｒｉａ　ｓｐｐ．）、黄化萎縮病（Ｓｃｌｅｒｏｐｈｔｈｏｒａ　ｍａｃｒｏｓｐｏｒａ）、白葉枯病（Ｘａｎｔｈｏｍｏｎａｓ　ｏｒｙｚａｅ　ｐｖ．　ｏｒｙｚａｅ）、褐条病（Ａｃｉｄｏｖｏｒａｘ　ａｖｅｎａｅ　ｓｕｂｓｐ．　ａｖｅｎａｅ）、内頴褐変病（Ｅｒｗｉｎｉａ　ａｎａｎａｓ）、苗立枯細菌病（Ｂｕｒｋｈｏｌｄｅｒｉａ　ｐｌａｎｔａｒｉｉ）、もみ枯細菌病（Ｂｕｒｋｈｏｌｄｅｒｉａ　ｇｌｕｍａｅ）、葉鞘褐変病（Ｐｓｅｕｄｏｍｏｎａｓ　ｆｕｓｃｏｖａｇｉｎａｅ）、かさ枯病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．ｏｒｙｚａｅ）、株腐病（Ｅｒｗｉｎｉａ　ｃｈｒｙｓａｎｔｈｅｍｉ）、黄萎病（Ｐｈｙｔｏｐｌａｓｍａ　ｏｒｙｚａｅ）、縞葉枯病（Ｒｉｃｅ　ｓｔｒｉｐｅ　ｔｅｎｕｉｖｉｒｕｓ）、萎縮病（Ｒｉｃｅ　ｄｗａｒｆ　ｒｅｏｖｉｒｕｓ）；
ムギ類のうどんこ病（Ｂｌｕｍｅｒｉａ　ｇｒａｍｉｎｉｓ　ｆ．ｓｐ．ｈｏｒｄｅｉ；　ｆ．ｓｐ．ｔｒｉｔｉｃｉ）、さび病（Ｐｕｃｃｉｎｉａ　ｓｔｒｉｉｆｏｒｍｉｓ、　Ｐｕｃｃｉｎｉａ　ｇｒａｍｉｎｉｓ、Ｐｕｃｃｉｎｉａ　ｒｅｃｏｎｄｉｔａ、Ｐｕｃｃｉｎｉａ　ｈｏｒｄｅｉ）、斑葉病（Ｐｙｒｅｎｏｐｈｏｒａ　ｇｒａｍｉｎｅａ）、網斑病（Ｐｙｒｅｎｏｐｈｏｒａ　ｔｅｒｅｓ）、赤かび病（Ｇｉｂｂｅｒｅｌｌａ　ｚｅａｅ、Ｆｕｓａｒｉｕｍ　ｃｕｌｍｏｒｕｍ、Ｆｕｓａｒｉｕｍ　ａｖｅｎａｃｅｕｍ、Ｍｏｎｏｇｒａｐｈｅｌｌａ　ｎｉｖａｌｉｓ）、雪腐病（Ｔｙｐｈｕｌａ　ｉｎｃａｒｎａｔａ、Ｔｙｐｈｕｌａ　ｉｓｈｉｋａｒｉｅｎｓｉｓ、Ｍｏｎｏｇｒａｐｈｅｌｌａ　ｎｉｖａｌｉｓ）、裸黒穂病（Ｕｓｔｉｌａｇｏ　ｎｕｄａ）、なまぐさ黒穂病（Ｔｉｌｌｅｔｉａ　ｃａｒｉｅｓ、Ｔｉｌｌｅｔｉａ　ｃｏｎｔｒｏｖｅｒｓａ）、眼紋病（Ｐｓｅｕｄｏｃｅｒｃｏｓｐｏｒｅｌｌａ　ｈｅｒｐｏｔｒｉｃｈｏｉｄｅｓ）、株腐病（Ｃｅｒａｔｏｂａｓｉｄｉｕｍ　ｇｒａｍｉｎｅｕｍ）、雲形病（Ｒｈｙｎｃｈｏｓｐｏｒｉｕｍ　ｓｅｃａｌｉｓ）、葉枯病（Ｓｅｐｔｏｒｉａ　ｔｒｉｔｉｃｉ）、ふ枯病（Ｐｈａｅｏｓｐｈａｅｒｉａ　ｎｏｄｏｒｕｍ）、苗立枯病（Ｆｕｓａｒｉｕｍ　ｓｐｐ．、Ｐｙｔｈｉｕｍ　ｓｐｐ．、Ｒｈｉｚｏｃｔｏｎｉａ　ｓｐｐ．、Ｓｅｐｔｏｒｉａ　ｓｐｐ．、Ｐｙｒｅｎｏｐｈｏｒａ　ｓｐｐ．）、立枯病（Ｇａｅｕｍａｎｎｏｍｙｃｅｓ　ｇｒａｍｉｎｉｓ）、炭疽病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｇｒａｍｉｎｉｃｏｌａ）、麦角病（Ｃｌａｖｉｃｅｐｓ　ｐｕｒｐｕｒｅａ）、斑点病（Ｃｏｃｈｌｉｏｂｏｌｕｓ　ｓａｔｉｖｕｓ）、黒節病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．　ｓｙｒｉｎｇａｅ）；
トウモロコシの赤かび病（Ｇｉｂｂｅｒｅｌｌａ　ｚｅａｅ等）、苗立枯病（Ｆｕｓａｒｉｕｍ　ａｖｅｎａｃｅｕｍ、　Ｐｅｎｉｃｉｌｌｉｕｍ　ｓｐｐ、　Ｐｙｔｈｉｕｍ　ｓｐｐ．、Ｒｈｉｚｏｃｔｏｎｉａ　ｓｐｐ．）、さび病（Ｐｕｃｃｉｎｉａ　ｓｏｒｇｈｉ）、ごま葉枯病（Ｃｏｃｈｌｉｏｂｏｌｕｓ　ｈｅｔｅｒｏｓｔｒｏｐｈｕｓ）、黒穂病（Ｕｓｔｉｌａｇｏ　ｍａｙｄｉｓ）、炭疽病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｇｒａｍｉｎｉｃｏｌａ）、北方斑点病（Ｃｏｃｈｌｉｏｂｏｌｕｓ　ｃａｒｂｏｎｕｍ）、褐条病（Ａｃｉｄｏｖｏｒａｘ　ａｖｅｎａｅ　ｓｕｂｓｐ．　ａｖｅｎａｅ）、条斑細菌病（Ｂｕｒｋｈｏｌｄｅｒｉａ　ａｎｄｒｏｐｏｇｏｎｉｓ）、倒伏細菌病（Ｅｒｗｉｎｉａ　ｃｈｒｙｓａｎｔｈｅｍｉ　ｐｖ．　ｚｅａｅ）、萎ちょう細菌病（Ｅｒｗｉｎｉａ　ｓｔｅｗａｒｔｉｉ）；ブドウのべと病（Ｐｌａｓｍｏｐａｒａ　ｖｉｔｉｃｏｌａ）、さび病（Ｐｈｙｓｏｐｅｌｌａ　ａｍｐｅｌｏｐｓｉｄｉｓ）、うどんこ病（Ｕｎｃｉｎｕｌａ　ｎｅｃａｔｏｒ）、黒とう病（Ｅｌｓｉｎｏｅ　ａｍｐｅｌｉｎａ）、晩腐病（Ｇｌｏｍｅｒｅｌｌａ　ｃｉｎｇｕｌａｔａ、　Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ａｃｕｔａｔｕｍ）、黒腐病（Ｇｕｉｇｎａｒｄｉａ　ｂｉｄｗｅｌｌｉｉ）、つる割病（Ｐｈｏｍｏｐｓｉｓ　ｖｉｔｉｃｏｌａ）、すす点病（Ｚｙｇｏｐｈｉａｌａ　ｊａｍａｉｃｅｎｓｉｓ）、灰色かび病（Ｂｏｔｒｙｔｉｓ　ｃｉｎｅｒｅａ）、芽枯病（Ｄｉａｐｏｒｔｈｅ　ｍｅｄｕｓａｅａ）、紫紋羽病（Ｈｅｌｉｃｏｂａｓｉｄｉｕｍ　ｍｏｍｐａ）、白紋羽病（Ｒｏｓｅｌｌｉｎｉａ　ｎｅｃａｔｒｉｘ）、根頭がんしゅ病（Ａｇｒｏｂａｃｔｅｒｉｕｍ　ｖｉｔｉｓ）；リンゴのうどんこ病（Ｐｏｄｏｓｐｈａｅｒａ　ｌｅｕｃｏｔｒｉｃｈａ）、黒星病（Ｖｅｎｔｕｒｉａ　ｉｎａｅｑｕａｌｉｓ）、斑点落葉病（Ａｌｔｅｒｎａｒｉａ　ｍａｌｉ）、赤星病（Ｇｙｍｎｏｓｐｏｒａｎｇｉｕｍ　ｙａｍａｄａｅ）、モニリア病（Ｍｏｎｉｌｉｎｉａ　ｍａｌｉ）、腐らん病（Ｖａｌｓａ　ｃｅｒａｔｏｓｐｅｒｍａ）、輪紋病（Ｂｏｔｒｙｏｓｐｈａｅｒｉａ　ｂｅｒｅｎｇｅｒｉａｎａ）、炭疽病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ａｃｕｔａｔｕｍ、Ｇｌｏｍｅｒｅｌｌａ　ｃｉｎｇｕｌａｔａ）、すす点病（Ｚｙｇｏｐｈｉａｌａ　ｊａｍａｉｃｅｎｓｉｓ）、すす斑病（Ｇｌｏｅｏｄｅｓ　ｐｏｍｉｇｅｎａ）、黒点病（Ｍｙｃｏｓｐｈａｅｒｅｌｌａ　ｐｏｍｉ）、紫紋羽病（Ｈｅｌｉｃｏｂａｓｉｄｉｕｍ　ｍｏｍｐａ）、白紋羽病（Ｒｏｓｅｌｌｉｎｉａ　ｎｅｃａｔｒｉｘ）、胴枯病（Ｐｈｏｍｏｐｓｉｓ　ｍａｌｉ、Ｄｉａｐｏｒｔｈｅ　ｔａｎａｋａｅ）、褐斑病（Ｄｉｐｌｏｃａｒｐｏｎ　ｍａｌｉ）、リンゴの火傷病（Ｅｒｗｉｎｉａ　ａｍｙｌｏｖｏｒａ）、根頭がんしゅ病（Ａｇｒｏｂａｃｔｅｒｉｕｍ　ｔｕｍｅｆａｃｉｅｎｓ）、毛根病（Ａｇｒｏｂａｃｔｅｒｉｕｍ　ｒｈｉｚｏｇｅｎｅｓ）；
ナシの黒斑病（Ａｌｔｅｒｎａｒｉａ　ｋｉｋｕｃｈｉａｎａ）、黒星病（Ｖｅｎｔｕｒｉａ　ｎａｓｈｉｃｏｌａ）、赤星病（Ｇｙｍｎｏｓｐｏｒａｎｇｉｕｍ　ａｓｉａｔｉｃｕｍ）、輪紋病（Ｂｏｔｒｙｏｓｐｈａｅｒｉａ　ｂｅｒｅｎｇｅｒｉａｎａ　ｆ．ｓｐ．　ｐｉｒｉｃｏｌａ）、胴枯病（Ｐｈｏｍｏｐｓｉｓ　ｆｕｋｕｓｈｉｉ）、枝枯細菌病（Ｅｒｗｉｎｉａ　ｓｐ．）、根頭がんしゅ病（Ａｇｒｏｂａｃｔｅｒｉｕｍ　ｔｕｍｅｆａｃｉｅｎｓ）、さび色胴枯病（Ｅｒｗｉｎｉａ　ｃｈｒｙｓａｎｔｈｅｍｉ　ｐｖ．　ｃｈｒｙｓａｎｔｈｅｍｉ）、花腐細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．　ｓｙｒｉｎｇａｅ）；セイヨウナシの疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｃａｃｔｏｒｕｍ、　Ｐｈｙｔｏｐｈｔｈｏｒａ　ｓｙｒｉｎｇａｅ）、枝枯細菌病（Ｅｒｗｉｎｉａ　ｓｐ．）；モモの黒星病（Ｃｌａｄｏｓｐｏｒｉｕｍ　ｃａｒｐｏｐｈｉｌｕｍ）、ホモプシス腐敗病（Ｐｈｏｍｏｐｓｉｓ　ｓｐ．）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｓｐ．）、炭疽病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｇｌｏｅｏｓｐｏｒｉｏｉｄｅｓ）、縮葉病（Ｔａｐｈｒｉｎａ　ｄｅｆｏｒｍａｎｓ）、穿孔細菌病（Ｘｈａｎｔｈｏｍｏｎａｓ　ｃａｍｐｅｓｔｒｉｓ　ｐｖ．　ｐｒｕｎｉ）、根頭がんしゅ病（Ａｇｒｏｂａｃｔｅｒｉｕｍ　ｔｕｍｅｆａｃｉｅｎｓ）；オウトウの炭疽病（Ｇｌｏｍｅｒｅｌｌａ　ｃｉｎｇｕｌａｔａ）、幼果菌核病（Ｍｏｎｉｌｉｎｉａ　ｋｕｓａｎｏｉ）、灰星病（Ｍｏｎｉｌｉｎｉａ　ｆｒｕｃｔｉｃｏｌａ）、根頭がんしゅ病（Ａｇｒｏｂａｃｔｅｒｉｕｍ　ｔｕｍｅｆａｃｉｅｎｓ）、樹脂細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．　ｓｙｒｉｎｇａｅ）；カキの炭疽病（Ｇｌｏｍｅｒｅｌｌａ　ｃｉｎｇｕｌａｔａ）、落葉病（Ｃｅｒｃｏｓｐｏｒａ　ｋａｋｉ；　Ｍｙｃｏｓｐｈａｅｒｅｌｌａ　ｎａｗａｅ）、うどんこ病（Ｐｈｙｌｌａｃｔｉｎｉａ　ｋａｋｉｋｏｒａ）、根頭がんしゅ病（Ａｇｒｏｂａｃｔｅｒｉｕｍ　ｔｕｍｅｆａｃｉｅｎｓ）；カンキツの黒点病（Ｄｉａｐｏｒｔｈｅ　ｃｉｔｒｉ）、緑かび病（Ｐｅｎｉｃｉｌｌｉｕｍ　ｄｉｇｉｔａｔｕｍ）、青かび病（Ｐｅｎｉｃｉｌｌｉｕｍ　ｉｔａｌｉｃｕｍ）、そうか病（Ｅｌｓｉｎｏｅ　ｆａｗｃｅｔｔｉｉ）、褐色腐敗病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｃｉｔｒｏｐｈｔｈｏｒａ）、かいよう病（Ｘｈａｎｔｈｏｍｏｎａｓ　ｃａｍｐｅｓｔｒｉｓ　ｐｖ．　ｃｉｔｒｉ）、褐斑細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．　ｓｙｒｉｎｇａｅ）、グリーニング病（Ｌｉｂｅｒｉｂａｃｔｏｒ　ａｓｉａｔｉｃｕｓ）、根頭がんしゅ病（Ａｇｒｏｂａｃｔｅｒｉｕｍ　ｔｕｍｅｆａｃｉｅｎｓ）；
トマト、キュウリ、豆類、イチゴ、ジャガイモ、キャベツ、ナス、レタス等の灰色かび病（Ｂｏｔｒｙｔｉｓ　ｃｉｎｅｒｅａ）；トマト、キュウリ、豆類、イチゴ、ジャガイモ、ナタネ、キャベツ、ナス、レタス等の菌核病（Ｓｃｌｅｒｏｔｉｎｉａ　ｓｃｌｅｒｏｔｉｏｒｕｍ）；トマト、キュウリ、豆類、ダイコン、スイカ、ナス、ナタネ、ピーマン、ホウレンソウ、テンサイ等各種野菜の苗立枯病（Ｒｈｉｚｏｃｔｏｎｉａ　ｓｐｐ．、Ｐｙｔｈｉｕｍ　ｓｐｐ．、Ｆｕｓａｒｉｕｍ　ｓｐｐ．、Ｐｈｙｔｈｏｐｈｔｈｏｒａ　ｓｐｐ．、Ｓｃｌｅｒｏｔｉｎｉａ　ｓｃｌｅｒｏｔｉｏｒｕｍ等）；ナス科植物の青枯病（Ｒａｌｓｔｏｎｉａ　ｓｏｌａｎａｃｅａｒｕｍ）；ウリ類のべと病（Ｐｓｅｕｄｏｐｅｒｏｎｏｓｐｏｒａ　ｃｕｂｅｎｓｉｓ）、うどんこ病（Ｓｐｈａｅｒｏｔｈｅｃａ　ｆｕｌｉｇｉｎｅａ）、炭疽病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｏｒｂｉｃｕｌａｒｅ）、つる枯病（Ｄｉｄｙｍｅｌｌａ　ｂｒｙｏｎｉａｅ）、つる割病（Ｆｕｓａｒｉｕｍ　ｏｘｙｓｐｏｒｕｍ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｐａｒａｓｉｔｉｃａ、Ｐｈｙｔｏｐｈｔｈｏｒａ　ｍｅｌｏｎｉｓ、Ｐｈｙｔｏｐｈｔｈｏｒａ　ｎｉｃｏｔｉａｎａｅ、Ｐｈｙｔｏｐｈｔｈｏｒａ　ｄｒｅｃｈｓｌｅｒｉ、Ｐｈｙｔｏｐｈｔｈｏｒａ　ｃａｐｓｉｃｉ等）、褐斑細菌病（Ｘｈａｎｔｈｏｍｏｎａｓ　ｃａｍｐｅｓｔｒｉｓ　ｐｖ．ｃｕｃｕｒｂｉｔａｅ）、軟腐病（Ｅｒｗｉｎｉａ　ｃａｒｏｔｏｖｏｒａ　ｓｕｂｓｐ．　ｃａｒｏｔｏｖｏｒａ）、斑点細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．　ｌａｃｈｒｙｍａｎｓ）、縁枯細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｍａｒｇｉｎａｌｉｓ　ｐｖ．　ｍａｒｇｉｎａｌｉｓ）、がんしゅ病（Ｓｔｒｅｐｔｏｍｙｃｅｓ　ｓｐ．）、毛根病（Ａｇｒｏｂａｃｔｅｒｉｕｍ　ｒｈｉｚｏｇｅｎｅｓ）、キュウリモザイクウィルス（Ｃｕｃｕｍｂｅｒ　ｍｏｓａｉｃ　ｖｉｒｕｓ）；
トマトの輪紋病（Ａｌｔｅｒｎａｒｉａ　ｓｏｌａｎｉ）、葉かび病（Ｆｕｌｖｉａ　ｆｕｌｖａ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｉｎｆｅｓｔａｎｓ）、萎凋病（Ｆｕｓａｒｉｕｍ　ｏｘｙｓｐｏｒｕｍ）、根腐病（Ｐｙｔｈｉｕｍ　ｍｙｒｉｏｔｙｌｕｍ、Ｐｙｔｈｉｕｍ　ｄｉｓｓｏｔｏｃｕｍ）、炭疽病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｇｌｏｅｏｓｐｏｒｉｏｉｄｅｓ）、かいよう病（Ｃｌａｖｉｂａｃｔｅｒ　ｍｉｃｈｉｇａｎｅｎｓｉｓ）、茎えそ細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｃｏｒｒｕｇａｔａ）、黒斑細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｖｉｒｉｄｉｆｌａｖａ）、軟腐病（Ｅｒｗｉｎｉａ　ｃａｒｏｔｏｖｏｒａ　ｓｕｂｓｐ．　ｃａｒｏｔｏｖｏｒａ）、葉こぶ病（Ｃｒｙｎｅｂａｃｔｅｒｉｕｍ　ｓｐ．）、萎黄病（Ｐｈｙｔｏｐｌａｓｍａ　ａｓｔｅｒｉｓ）、黄化萎縮病（Ｔｏｂａｃｃｏ　ｌｅａｆ　ｃｕｒｌ　ｓｕｂｇｒｏｕｐ　ＩＩＩ　ｇｅｍｉｎｉｖｉｒｕｓ）；ナスのうどんこ病（Ｓｐｈａｅｒｏｔｈｅｃａ　ｆｕｌｉｇｉｎｅａ等）、すすかび病（Ｍｙｃｏｖｅｌｌｏｓｉｅｌｌａ　ｎａｔｔｒａｓｓｉｉ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｉｎｆｅｓｔａｎｓ）、褐色腐敗病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｃａｐｓｉｃｉ）、褐斑細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｃｉｃｈｏｒｉｉ）、茎えそ細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｃｏｒｒｕｇａｔａ）、茎腐細菌病（Ｅｒｗｉｎｉａ　ｃｈｒｙｓａｎｔｈｅｍｉ）、軟腐病（Ｅｒｗｉｎｉａ　ｃａｒｏｔｏｖｏｒａ　ｓｕｂｓｐ．　ｃａｒｏｔｏｖｏｒａ）、斑点細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｐ．）；ナタネの黒斑病（Ａｌｔｅｒｎａｒｉａ　ｂｒａｓｓｉｃａｅ）、黒腐病（Ｘｈａｎｔｈｏｍｏｎａｓ　ｃａｍｐｅｓｔｒｉｓ　ｐｖ．　　ｃａｍｐｅｓｔｒｉｓ）、黒斑細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．　ｍａｃｕｌｉｃｏｌａ）、軟腐病（Ｅｒｗｉｎｉａ　ｃａｒｏｔｏｖｏｒａ）；アブラナ科野菜の黒斑病（Ａｌｔｅｒｎａｒｉａ　ｂｒａｓｓｉｃａｅ等）、白斑病（Ｃｅｒｃｏｓｐｏｒｅｌｌａ　ｂｒａｓｓｉｃａｅ）、根朽病（Ｐｈｏｍａ　ｌｉｎｇａｍ）、根こぶ病（Ｐｌａｓｍｏｄｉｏｐｈｏｒａ　ｂｒａｓｓｉｃａｅ）、べと病（Ｐｅｒｏｎｏｓｐｏｒａ　ｐａｒａｓｉｔｉｃａ）、黒腐病（Ｘｈａｎｔｈｏｍｏｎａｓ　ｃａｍｐｅｓｔｒｉｓ　ｐｖ．　　ｃａｍｐｅｓｔｒｉｓ）、黒斑細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．　ｍａｃｕｌｉｃｏｌａ）、軟腐病（Ｅｒｗｉｎｉａ　ｃａｒｏｔｏｖｏｒａ　ｓｕｂｓｐ．　ｃａｒｏｔｏｖｏｒａ）；
キャベツの株腐病（Ｔｈａｎａｔｅｐｈｏｒｕｓ　ｃｕｃｕｍｅｒｉｓ）、萎黄病（Ｆｕｓａｒｉｕｍ　ｏｘｙｓｐｏｒｕｍ）、黒すす病（Ａｌｔｅｒｎａｒｉａ　ｂｒａｓｓｉｓｉｃｏｌａ）；ハクサイの尻腐病（Ｒｈｉｚｏｃｔｏｎｉａ　ｓｏｌａｎｉ）、黄化病（Ｖｅｒｔｉｃｉｌｌｉｕｍ　ｄａｈｌｉａｅ）；ネギのさび病（Ｐｕｃｃｉｎｉａ　ａｌｌｉｉ）、黒斑病（Ａｌｔｅｒｎａｒｉａ　ｐｏｒｒｉ）、白絹病（Ｓｃｌｅｒｏｔｉｕｍ　ｒｏｌｆｓｉｉ）、白色疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｐｏｒｒｉ）、黒腐菌核病（Ｓｃｌｅｒｏｔｉｕｍ　ｃｅｐｉｖｏｒｕｍ）；タマネギのかいよう病（Ｃｕｒｔｏｂａｃｔｅｒｉｕｍ　ｆｌａｃｃｕｍｆａｃｉｅｎｓ）、軟腐病（Ｅｒｗｉｎｉａ　ｃａｒｏｔｏｖｏｒａ　ｓｕｂｓｐ．　ｃａｒｏｔｏｖｏｒａ）、斑点細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．　ｓｙｒｉｎｇａｅ）、腐敗病（Ｅｒｗｉｎｉａ　ｒｈａｐｏｎｔｉｃｉ）、鱗片腐敗病（Ｂｕｒｋｈｏｌｄｅｒｉａ　ｇｌａｄｉｏｌｉ）、萎黄病（Ｐｈｙｔｏｐｌａｓｍａ　ａｓｔｅｒｉｓ）；ニンニクの軟腐病（Ｅｒｗｉｎｉａ　ｃａｒｏｔｏｖｏｒａ　ｓｕｂｓｐ．　ｃａｒｏｔｏｖｏｒａ）、春腐病（Ｐｓｅｕｄｏｍｏｎａｓ　ｍａｒｇｉｎａｌｉｓ　ｐｖ．ｍａｒｇｉｎａｌｉｓ）；ダイズの紫斑病（Ｃｅｒｃｏｓｐｏｒａ　ｋｉｋｕｃｈｉｉ）、黒とう病（Ｅｌｓｉｎｏｅ　ｇｌｙｃｉｎｅｓ）、黒点病（Ｄｉａｐｏｒｔｈｅ　ｐｈａｓｅｏｌｏｒｕｍ）、リゾクトニア根腐病（Ｒｈｉｚｏｃｔｏｎｉａ　ｓｏｌａｎｉ）、茎疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｓｏｊａｅ）、べと病（Ｐｅｒｏｎｏｓｐｏｒａ　ｍａｎｓｈｕｒｉｃａ）、さび病（Ｐｈａｋｏｐｓｏｒａ　ｐａｃｈｙｒｈｉｚｉ）、炭疽病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｔｒｕｎｃａｔｕｍ等）、葉焼病（Ｘｈａｎｔｈｏｍｏｎａｓ　ｃａｍｐｅｓｔｒｉｓ　ｐｖ．　　ｇｌｙｃｉｎｅｓ）、斑点細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．　ｇｌｙｃｉｎｅａ）；インゲンの炭疽病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｌｉｎｄｅｍｕｔｈｉａｎｕｍ）、青枯病（Ｒａｌｓｔｏｎｉａ　ｓｏｌａｎａｃｅａｒｕｍ）、かさ枯病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．　ｐｈａｓｅｏｌｉｃｏｌａ）、褐斑細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｖｉｒｉｄｉｆｌａｖａ）、葉焼病（Ｘｈａｎｔｈｏｍｏｎａｓ　ｃａｍｐｅｓｔｒｉｓ　ｐｖ．　ｐｈａｓｅｏｌｉ）；
ラッカセイの黒渋病（Ｍｙｃｏｓｐｈａｅｒｅｌｌａ　ｂｅｒｋｅｌｅｙｉ）、褐斑病（Ｍｙｃｏｓｐｈａｅｒｅｌｌａ　ａｒａｃｈｉｄｉｓ）、青枯病（Ｒａｌｓｔｏｎｉａ　ｓｏｌａｎａｃｅａｒｕｍ）；エンドウのうどんこ病（Ｅｒｙｓｉｐｈｅ　ｐｉｓｉ）、べと病（Ｐｅｒｏｎｏｓｐｏｒａ　ｐｉｓｉ）、つる枯細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．ｐｉｓｉ）、つる腐細菌病（Ｘｈａｎｔｈｏｍｏｎａｓ　ｃａｍｐｅｓｔｒｉｓ　ｐｖ．　ｐｉｓｉ；ソラマメのべと病（Ｐｅｒｏｎｏｓｐｏｒａ　ｖｉｃｉａｅ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｎｉｃｏｔｉａｎａｅ）；ジャガイモの夏疫病（Ａｌｔｅｒｎａｒｉａ　ｓｏｌａｎｉ）、黒あざ病（Ｔｈａｎａｔｅｐｈｏｒｕｓ　ｃｕｃｕｍｅｒｉｓ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｉｎｆｅｓｔａｎｓ）、銀か病（Ｈｅｌｍｉｎｔｈｏｓｐｏｒｉｕｍ　ｓｏｌａｎｉ）、乾腐病（Ｆｕｓａｒｉｕｍ　ｏｘｙｓｐｏｒｕｍ、Ｆｕｓａｒｉｕｍ　ｓｏｌａｎｉ）、粉状そうか病（Ｓｐｏｎｇｏｓｐｏｒａ　ｓｕｂｔｅｒｒａｎｅａ）、青枯病（Ｒａｌｓｔｏｎｉａ　ｓｏｌａｎａｃｅａｒｕｍ）、黒あし病（Ｅｒｗｉｎｉａ　ｃａｒｏｔｏｖｏｒａ　ｓｕｂｓｐ．　ａｔｒｏｓｅｐｔｉｃａ）、そうか病（Ｓｔｒｅｐｔｏｍｙｃｅｓ　ｓｃａｂｉｅｓ、Ｓｔｒｅｐｔｏｍｙｃｅｓ　ａｃｉｄｉｓｃａｂｉｅｓ）、軟腐病（Ｅｒｗｉｎｉａ　ｃａｒｏｔｏｖｏｒａ　ｓｕｂｓｐ．　ｃａｒｏｔｏｖｏｒａ）、粘性腐敗病（Ｃｒｏｓｔｒｉｄｉｕｍ　ｓｐｐ．）、輪腐病（Ｃｌａｖｉｂａｃｔｅｒ　ｍｉｃｈｉｇａｎｅｎｓｉｓ　ｓｕｂｓｐ．ｓｅｐｅｄｏｎｉｃｕｓ）；サツマイモの立枯病（Ｓｔｒｅｐｔｏｍｙｃｅｓ　ｉｐｏｍｏｅａｅ）；テンサイの褐斑病（Ｃｅｒｃｏｓｐｏｒａ　ｂｅｔｉｃｏｌａ）、べと病（Ｐｅｒｏｎｏｓｐｏｒａ　ｓｃｈａｃｈｔｉｉ）、黒根病（Ａｐｈａｎｏｍｙｃｅｓ　ｃｏｃｈｉｏｉｄｅｓ）、蛇の目病（Ｐｈｏｍａ　ｂｅｔａｅ）、根頭がんしゅ病（Ａｇｒｏｂａｃｔｅｒｉｕｍ　ｔｕｍｅｆａｃｉｅｎｓ）、そうか病（Ｓｔｒｅｐｔｏｍｙｃｅｓ　ｓｃａｂｉｅｓ）、斑点細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．　ａｐｔａｔａ）；
ニンジンの黒葉枯病（Ａｌｔｅｒｎａｒｉａ　ｄａｕｃｉ）、こぶ病（Ｒｈｉｚｏｂａｃｔｅｒ　ｄａｕｃｉ）、根頭がんしゅ病（Ａｇｒｏｂａｃｔｅｒｉｕｍ　ｔｕｍｅｆａｃｉｅｎｓ）、ストレプトミセスそうか病（Ｓｔｒｅｐｔｏｍｙｃｅｓ　ｓｐｐ．）、軟腐病（Ｅｒｗｉｎｉａ　ｃａｒｏｔｏｖｏｒａ　ｓｕｂｓｐ．　ｃａｒｏｔｏｖｏｒａ）；イチゴのうどんこ病（Ｓｐｈａｅｒｏｔｈｅｃａ　ａｐｈａｎｉｓ　ｖａｒ．　ａｐｈａｎｉｓ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｎｉｃｏｔｉａｎａｅ等）、炭疽病（Ｇｌｏｍｅｒｅｌｌａ　ｃｉｎｇｕｌａｔａ等）、果実腐敗病（Ｐｙｔｈｉｕｍ　ｕｌｔｉｍｕｍ）、青枯病（Ｒａｌｓｔｏｎｉａ　ｓｏｌａｎａｃｅａｒｕｍ）、角斑細菌病（Ｘｈａｎｔｈｏｍｏｎａｓ　ｃａｍｐｅｓｔｒｉｓ）、芽枯細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｍａｒｇｉｎａｌｉｓ　　ｐｖ．　ｍａｒｇｉｎａｌｉｓ）；チャの網もち病（Ｅｘｏｂａｓｉｄｉｕｍ　ｒｅｔｉｃｕｌａｔｕｍ）、白星病（Ｅｌｓｉｎｏｅ　ｌｅｕｃｏｓｐｉｌａ）、炭疽病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｔｈｅａｅ－ｓｉｎｅｎｓｉｓ）、輪斑病（Ｐｅｓｔａｌｏｔｉｏｐｓｉｓ　ｌｏｎｇｉｓｅｔａ）、赤焼病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．ｔｈｅａｅ）、かいよう病（Ｘｈａｎｔｈｏｍｏｎａｓ　ｃａｍｐｅｓｔｒｉｓ　ｐｖ．　ｔｈｅｉｃｏｌａ）、てんぐ巣病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｐ．）；タバコの赤星病（Ａｌｔｅｒｎａｒｉａ　ａｌｔｅｒｎａｔａ）、うどんこ病（Ｅｒｙｓｉｐｈｅ　ｃｉｃｈｏｒａｃｅａｒｕｍ）、炭疽病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｇｌｏｅｏｓｐｏｒｉｏｉｄｅｓ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｎｉｃｏｔｉａｎａｅ）、野火病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．ｔａｂａｃｉ）、黄がさ細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．ｍｅｌｌｅａ）、空洞病（Ｅｒｗｉｎｉａ　ｃａｒｏｔｏｖｏｒａ　ｓｕｂｓｐ．　ｃａｒｏｔｏｖｏｒａ）、立枯病（Ｒａｌｓｔｏｎｉａ　ｓｏｌａｎａｃｅａｒｕｍ）、タバコモザイクウィルス（Ｔｏｂａｃｃｏ　ｍｏｓａｉｃ　ｖｉｒｕｓ）；
コーヒーのさび病（Ｈｅｍｉｌｅｉａ　ｖａｓｔａｔｒｉｘ）；バナナの黒シガトガ病（Ｍｙｃｏｓｐｈａｅｒｅｌｌａ ｆｉｊｉｅｎｓｉｓ）、パナマ病（Ｆｕｓａｒｉｕｍ　ｏｘｙｓｐｏｒｕｍ　ｆ．ｓｐ　ｃｕｂｅｎｓｅ）；ワタの立枯病（Ｆｕｓａｒｉｕｍ　ｏｘｙｓｐｏｒｕｍ）、白かび病（Ｒａｍｕｌａｒｉａ　ａｒｅｏｌａ）；ヒマワリの菌核病（Ｓｃｌｅｒｏｔｉｎｉａ　ｓｃｌｅｒｏｔｉｏｒｕｍ）、角点病（Ｘｈａｎｔｈｏｍｏｎａｓ　ｃａｍｐｅｓｔｒｉｓ　ｐｖ．ｍａｌｖａｃｅａｒｕｍ）、空洞病（Ｅｒｗｉｎｉａ　ｃａｒｏｔｏｖｏｒａ　ｓｕｂｓｐ．　ｃａｒｏｔｏｖｏｒａ）、斑点細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｓｙｒｉｎｇａｅ　ｐｖ．ｈｅｌｉａｎｔｈｉ）；バラの黒星病（Ｄｉｐｌｏｃａｒｐｏｎ　ｒｏｓａｅ）、うどんこ病（Ｓｐｈａｅｒｏｔｈｅｃａ　ｐａｎｎｏｓａ等）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｍｅｇａｓｐｅｒｍａ）、べと病（Ｐｅｒｏｎｏｓｐｏｒａ　ｓｐａｒｓａ）、根頭がんしゅ病（Ａｇｒｏｂａｃｔｅｒｉｕｍ　ｔｕｍｅｆａｃｉｅｎｓ）；キクの褐斑病（Ｓｅｐｔｏｒｉａ　ｏｂｅｓａ）、白さび病（Ｐｕｃｃｉｎｉａ　ｈｏｒｉａｎａ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｃａｃｔｏｒｕｍ）、斑点細菌病（Ｐｓｅｕｄｏｍｏｎａｓ　ｃｉｃｈｏｒｉｉ）、軟腐病（Ｅｒｗｉｎｉａ　ｃａｒｏｔｏｖｏｒａ　ｓｕｂｓｐ．　ｃａｒｏｔｏｖｏｒａ）、根頭がんしゅ病（Ａｇｒｏｂａｃｔｅｒｉｕｍ　ｔｕｍｅｆａｃｉｅｎｓ）、毛根病（Ａｇｒｏｂａｃｔｅｒｉｕｍ　ｒｈｉｚｏｇｅｎｅｓ）、緑化病（Ｐｈｙｔｏｐｌａｓｍａ　ａｕｒａｎｔｉｆｏｌｉａ）；芝のブラウンパッチ病（Ｒｈｉｚｏｃｔｏｎｉａ　ｓｏｌａｎｉ）、ダラースポット病（Ｓｃｌｅｒｏｔｉｎｉａ　ｈｏｍｏｅｏｃａｒｐａ）、カーブラリア葉枯病（Ｃｕｒｖｕｌａｒｉａ　ｓｐ．）、さび病　（Ｐｕｃｃｉｎｉａ　ｚｏｙｓｉａｅ）、ヘルミントスポリウム葉枯病（Ｃｏｃｈｌｉｏｂｏｌｕｓ　ｓｐ．）、雲形病（Ｒｈｙｎｃｈｏｓｐｏｒｉｕｍ　ｓｅｃａｌｉｓ）、立枯病（Ｇａｅｕｍａｎｎｏｍｙｃｅｓ　ｇｒａｍｉｎｉｓ）、炭疽病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｓｐ．）、雪腐褐色小粒菌核病（Ｔｙｐｈｕｌａ　ｉｎｃａｒｎａｔａ）、雪腐黒色小粒菌核病（Ｔｙｐｈｕｌａ　ｉｓｈｉｋａｒｉｅｎｓｉｓ）、雪腐大粒菌核病（Ｍｙｒｉｏｓｃｌｅｒｏｔｉｎｉａ　ｂｏｒｅａｌｉｓ）、フェアリーリング病（Ｍａｒａｓｍｉｕｓ　ｏｒｅａｄｅｓ等）、ピシウム病（Ｐｙｔｈｉｕｍ　ａｐｈａｎｉｄｅｒｍａｔｕｍ等）、いもち病（Ｐｙｒｉｃｕｌａｒｉａ　ｇｒｉｓｅａ）等が挙げられる。 Rice blast (Magnaporthe grisea), sheath blight (Thanatephorus cucumeris), brown rot (Ceratobasidium setariae), brown sclerotium (Waitea circinata), brown spot rot spelling bacterium (Therca erucorus phus) Sclerotium hydrophilum, red rot (Wairea circinata), black rot (Entyloma dactylidis), pneumococcal disease (Magnaporthe salvinii leaf blight, Ceratobosa sigma rot) Blight disease (Sphaerulina oryzina) , Frog seedling disease (Gibberella fujikuroi), seedling blight (Pythium spp., Fusarium spp., Trichoderma spp., Rhizopus spp., Rhizonia spore, Rhizoctonia spore, Rhizoptonia solipani, Ms. Rhizotonia sol. Achlya spp., Dictyuchus spp.), Rice scab (Clavipesps virens), Black smut (Tilletia barclayana), Brown rice (Curvularia spp., Alternaria spp., Yellow wilt disease, Alternaria spp., Yellowing disease) Xanthomonas oryzae pv. Oryzae, brown streak (Acidovora) avenae subsp. oryzae), strain rot (Erwinia chrysanthemi), yellow dwarf (Phytoplasma oryzae), Rice stripe tenuivirus, dwarf disease (Rice dwarf revirus);
Powdery mildew of wheat (Blumeria graminis f. Sp. Hordei; f. Sp. Tritici), rust (Puccinia striiformis, Puccinia graminis, Puccinia reconitia, Puccinia reconia, Puccinia reconia, Puccinia reconia, Puccinia reconitia, Puccinia reconitia) Pyrenophora teres), Fusarium zeae, Fusarium culmorum, Fusarium avenaceum, Monographella nivalis, Snow rot (Typhula incarina, Typhula inicarina, Typhula iniganeis raisulai sushi) nuda), fishy smell smut (Tilletia caries, Tilletia controversa), Memonbyo (Pseudocercosporella herpotrichoides), stock rot (Ceratobasidium gramineum), scald (Rhynchosporium secalis), leaf blight (Septoria tritici), glume blotch (Phaeosphaeria nodorum), Fusarium spp., Pythium spp., Rhizoctonia spp., Septoria spp., Pyrenophora spp.), Wilt blight (Gaeumanomyces gramminolitis) Ergot (Claviceps purpurea), Leaf spot (Cochliobolus sativus), Black spot (Pseudomonas syringae pv. Syringae);
Fusarium avenaceum, Penicillium spp, Pythium spp., Rhizoctonia spp., Pustinia sorghum scab (Puccinia sorghum), rust (Puccinia sorghum), and rust (Puccinia sorghum), corn leafy mildew (Gibberella zeae, etc.), seedling blight (Fusarium avenaceum, Penicillium spp, Pythium spp., Rhizoctonia sp. Ustilago maydis, anthrax (Colletotrichum graminicola), northern leaf spot (Cochliobolus carbumum), brown streak (Acidovorax avene ssp. ), Fusarium wilt disease (Erwinia stewartii); Grape downy mildew (Plasmopara viticola), rust (Physopella ampelopsidis), powdery mildew (Uncinula necrotor, Elus erin aelin erin aelin erin aelin ell erin ella melin elsa) , Colletotrichum acutatum, black rot (Guignardia bidwellii), vine disease (Phomopsis viticola), soybean spot disease (Zygophiala jamaicensis), gray mold disease (Butterydiae blight disease) Helicobasidium mompa), white crest Disease (Rosellinia necatrix), apical carcinoma disease (Agrobacterium vitis); powdery mildew of apples (Podosphaera leucotricha), scab (Venturia inaealia, red leaf sprouts (Alternaria ganaria nymph) Diseases (Monilinia mali), rot (Valsa ceratosperma), ring spot (Botryosphaeria berengeriana), anthrax (Colletotrichum acutatum espodia, gomaella singula sigma, swelling) ena), black spot disease (Mycosphaerella pomi), purple root rot (Helicobasium momopa), white root rot (Rosellinia necatrix), blight disease (Phomopsis mali, Diaporthe tanako papaya tanako papaya) Injury and disease (Erwinia amylovora), apical carcinoma (Agrobacterium tumefaciens), hairy root disease (Agrobacterium rhizogenes);
Pear black spot (Alternaria kikuchiana), scab (Venturia nasicola), scab (Gymnosporangium asiaticum), ring spot (Botryosphaeria wisp, sclerosis, sclerosis, sclerosis, and so on). Erwinia sp.), Apical carcinoma (Agrobacterium tumefaciens), rust-colored blight (Erwinia chrysanthemi pv. Chrysanthemi), and rot bacterial disease (Pseudomonas syringa spores). s ringae), bacterial wilt disease (Erwinia sp.); peach scab (Cladosporium carpophilum), homopsis rot (Phomopsis sp.), plague (Phytophthora spp.), and anthrax (Colletotrophithosporium). deformans), perforated bacterial disease (Xhanthomonas campestris pv. pruni), apical carcinoma disease (Agrobacterium tumefaciens); cherry anthracnose (Glomerella singulata), and germ fungus sclerosis (Milica koniota milion) ), Apical carcinoma (Agrobacter) um tumefaciens, resin bacterial disease (Pseudomonas syringae pv. syringae); oyster anthracnose (Glomerella cingulata), deciduous disease (Cercospora kaki; tumefaciens; citrus black spot (Diaporthe citri), green mold (Penicillium digitatum), blue mold (Penicillium italicum), scab (Elsinoe fawcetti, brown rot or phrotch phthosis) omonas campestris pv. citri), brown spot bacterial disease (Pseudomonas syringae pv. syringae), greening disease (Liberactor asiaticus), apical carcinoma (Agrobacterium tumefaciens);
Botrytis cinerea such as tomato, cucumber, beans, strawberries, potatoes, cabbage, eggplant, lettuce; sclerotinia sclerotium such as tomato, cucumber, beans, strawberry, potato, rapeseed, cabbage, eggplant, lettuce ); Tomato, cucumber, legumes, radish, watermelon, eggplant, rapeseed, bell pepper, spinach, sugar beet, and various other types of seedling wilt (Rhizoctonia spp., Pythium spp., Fusarium spp., Phylophthroprosa sp., Etc.) Rustonia solanacearum of Solanaceae; downy mildew of cucumber (Pseudoperonospora cubens); s), powdery mildew (Sphaerotheca fuliginea), anthracnose (Colletotrichum orbiculare), vine blight (Didymella bryoniae), Fusarium disease (Fusarium oxysporum), plague (Phytophthora parasitica, Phytophthora melonis, Phytophthora nicotianae, Phytophthora drechsleri, Phytophthora capsici Etc.), brown spot bacterial disease (Xhanthomonas campestris pv. Cucurbitae), soft rot (Erwinia carotovora subsp. Carotovora), spot bacterial disease (Pseudomonas syri) ... Gae pv lachrymans), edges bacterial grain rot (Pseudomonas marginalis pv marginalis), temple petitioner disease (Streptomyces sp), root disease (Agrobacterium rhizogenes), cucumber mosaic virus (Cucumber mosaic virus);
Tomato ring spot (Alternaria solani), leaf mold (Fulvia fulva), plague (Phytophthora infestans), wilt (Fusarium oxysporum), root rot (Pythium myriotium sulcus, Pythium myriotium illum, pythium myriotylum lysium) Diseases (Claviobacter michiganensis), Stem Necrotic Bacterial Disease (Pseudomonas corrugata), Black Spot Bacterial Disease (Pseudomonas viridiflava), Soft Rot (Erwinia carrotova sp. ytoplasma asteris), yellow dwarf (Tobacco leaf curl subgroup III geminivirus); Brown spot bacterial disease (Pseudomonas cichorii), stem nematode bacterial disease (Pseudomonas corrugata), stem rot bacterial disease (Erwinia chrysanthemi), soft rot (Erwinia carotovora spores, spores of spores, spores, spores, spores, spores, spores and germs). Black rot (Alternaria brassicae), black rot (Xhanthomonas campestris pv. Campestris), black rot (Pseudomonas syringae pv. Eravia kuroa eroa var. Etc.), white spot disease (Cercosporella brassicae), root rot disease (Pharma lingam), clubroot disease (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), black rot disease (Xhancamposamposa. campestris), black spot bacterial disease (Pseudomonas syringae pv. maculicola), soft rot (Erwinia carotovora subsp. carotovora);
Cabbage plant rot (Thanatephorus cucumeris), yellow rot (Fusarium oxysporum), black scab (Alternaria brassicicola); Chinese cabbage rot (Rhizotnia sulnia erutia succinata) ), Black spot disease (Alternaria porri), white silk disease (Sclerotium rolfsii), white plague (Phytophthora porri), black rot fungus (Sclerotium sepivorum); onion scab (curtobacterium erobicum erobicum erium wilt disease) Carot vora), spot bacterial disease (Pseudomonas syringae pv. syringae), rot (Erwinia rhapontici), scale rot (Burkholderia gladioli rot), and yellow rot (Phytoplasa saunia rot). Disease (Pseudomonas marginalis pv. Marginalis); soybean purpura (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phasoolz, rhizopha spores and lysophia rotoh rotoh rotonia sarcopodium) e), downy mildew (Peronospora manshurica), rust (Phakopsora pachyrhizi), anthrax (Colletotrichum truncatum, etc.), leaf blight (Xanthomonas camps pesgos pest. Anthrax (Colletotrichum lindemutianum), bacterial wilt (Ralstonia solanacearum), scab (Pseudomonas syringae pv. Phaseolicola), brown spot bacterial disease (Pseudomonas visamrais virions virion virion virion virion sv. v. phaseoli);
Peanut black spot (Mycosphaerella berkeleyi), brown spot (Mycosphaerella arachidis), wilt (Ralstonia solanacearum); pea powdery mildew (Erysiphe pisi), downy mildew (Peros pero spelling, Peros pero spelling, downy mildew) syringae pv. pisi, vine rot (Xhanthomonas campestris pv. pisi; broad bean downy mildew (Peronospora viciiae), plague (Phytothora nichoantia, black rot) Plague (Phyt phthora infestans, silver blight (Helminthosporium solani), dry rot (Fusarium oxysporum, Fusarium solani), powdery scab (Spongospora sarva sultan seroa sultan seroa sarva sarcoa rusta sarcoa) ), Scab (Streptomyces scabies, Streptomyces acidiscabies), soft rot (Erwinia carotovora subsp. Carotovora), viscous rot (Crostridium spicia sibim. Sweetpotato wilt (Streptomyces ipomoea); Sugar beet brown spot (Cercospora beticola), downy mildew (Peronospora schachyti), black root rot (Aphanomychoes schoensis, Aphanomychoes schoensis). Agrobacterium tumefaciens, scab (Streptomyces scabies), spot bacterial disease (Pseudomonas syringae pv. Apata);
Bacterial leaf blight of carrots (Alternaria dauci), club scab (Rhizobacter dauci), apical carcinoma (Agrobacterium tumefaciens), Streptomyces scab (Streptomyces spop. Powdery mildew of strawberry (Sphaerotheca aphanis var. Aphanis), plague (Phytophthora nicotiana, etc.), anthrax (Glomerella singulata, etc.), fruit rot (Pythium ultimum), bacterial rot (Stium rustum), Xanthus wilt disease, Xanthus wilt disease campestris), Bacterial blight (Pseudomonas marginalis pv. Marginalis); tea blast (Exobasidium reticulatum), white scab (Elsinoe leucospila), anthrax (Colletotrichus stomach disease) syringae pv. theae, scabs (Xhanthomonas campestris pv. theicola), goblet's scab (Pseudomonas sp.); hum gloeosporioides), late blight (Phytophthora nicotianae), Wildfire Disease (Pseudomonas syringae pv.tabaci), Huang and bacterial diseases (Pseudomonas syringae pv.mellea), cavity disease (Erwinia carotovora subsp. carotovora), damping off (Ralstonia solanacearum) , Tobacco mosaic virus;
Rust of coffee (Hemileia vastatrix); Black sigatoga disease of banana (Mycosphaerella fijiensis), Panama disease (Fusarium oxysporum f. Sp cubense); Cotton wilt disease (Fusaria moria, R. sarcoa) Sclerotinia sclerotiorum, Xanthomonas campestris pv. Malvacearum, scab (Erwinia carotovora subsp. Carovora), spotted bacterial disease (P. erosp. Fusarium sickness (Sphaerotheca pannosa, etc.), plague (Phytophthora megasperma), downy mildew (Peronospora sparsa), root carcinoma (Agrobacterium tumefaciens), chrysanthemum spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore spore sb. ), Plague (Phytophthora actorum), spot bacterial disease (Pseudomonas ichorii), soft rot (Erwinia carotovora subsp. ifolia); turf brown patch disease (Rhizoctonia solani), dollar spot disease (Sclerotinia homoeocarpa), carburaria leaf blight (Curvularia sp.), rust (Puccinia zoysia sp. , Scallops (Rynchosporium secalis), wilt (Gaeumannomyces graminis), anthrax (Colletotrichum sp.), Snow rot brown sclerotia (Typhula incarnata), snow rot black sclerophyll sari shirahi shira shira shira shira shira shira shira shira shira shira shira shira shira shikotsuka Bacterial bacterial rot (Myrioscleroticia borealis), fairy ring disease (Marasius oreades etc.), Pycium disease (Pythium aphanidermatum etc.), Blast disease (Pyricularia grisea) and the like.
　本発明化合物は、本化合物単体で使用してもよいが、好ましくは、固体担体、液体担体、気体担体、界面活性剤、固着剤、分散剤、安定剤等と混合し、粉剤、水和剤、顆粒水和剤、水溶剤、顆粒水溶剤、粒剤、乳剤、液剤、マイクロエマルション剤、水性懸濁製剤、水性乳濁製剤、サスポエマルション製剤等の組成物として使用することができる。効果が発揮される限りにおいて、それらの組成物に限定されることはない。 The compound of the present invention may be used alone, but preferably is mixed with a solid carrier, liquid carrier, gas carrier, surfactant, fixing agent, dispersant, stabilizer, etc. It can be used as a composition such as water dispersible granules, aqueous solvents, aqueous granule solvents, granules, emulsions, liquids, microemulsions, aqueous suspensions, aqueous emulsions, and suspoemulsions. The composition is not limited as long as the effect is exhibited.
　以下に具体的な製剤化例を示すが、これらに限定されるものではない。 具体 Specific examples of formulation are shown below, but are not limited thereto.
［製剤例１　フロアブル剤］
　本発明化合物（１０質量部）、ナフタレンスルホン酸のホルムアルデヒド縮合物ナトリウム塩（５質量部）、ポリオキシエチレンアリールフェニルエーテル（１質量部）、プロピレングリコール（５質量部）、シリコン系消泡剤（０．１質量部）、キサンタンガム（０．２質量部）、イオン交換水（７８．７質量部）を混合してスラリーとなし、さらにダイノミルＫＤＬで直径１．０ｍｍのガラスビーズを用いて湿式粉砕しフロアブル剤を得る。 [Formulation Example 1 Flowable]
Compound of the present invention (10 parts by mass), sodium salt of formaldehyde condensate of naphthalenesulfonic acid (5 parts by mass), polyoxyethylene arylphenyl ether (1 part by mass), propylene glycol (5 parts by mass), silicon-based antifoaming agent ( 0.1 parts by mass), xanthan gum (0.2 parts by mass), ion-exchanged water (78.7 parts by mass) to form a slurry, and further wet milling using glass beads having a diameter of 1.0 mm with Dynomill KDL. To obtain a flowable agent.
［製剤例２　乳剤］
　本発明化合物（５質量部）をキシレン（４０質量部）とシクロヘキサン（３５質量部）の混合溶液に溶解し、この溶液にＴｗｅｅｎ２０（２０質量部）を添加混合し、乳剤を得る。 [Formulation Example 2 Emulsion]
The compound of the present invention (5 parts by mass) is dissolved in a mixed solution of xylene (40 parts by mass) and cyclohexane (35 parts by mass), and Tween 20 (20 parts by mass) is added and mixed with the solution to obtain an emulsion.
［製剤例３　水和剤］
　本発明化合物（１０質量部）、ホワイトカーボン（１０質量部）、ポリビニルアルコール（２質量部）、ジオクチルスルホコハク酸ナトリウム塩（０．５質量部）、アルキルベンゼンスルホン酸ナトリウム塩（５質量部）、焼成珪藻土（１０質量部）およびカオリナイトクレー（６２．５質量部）を充分に混合し、エアーミルで粉砕し、水和剤を得る。 [Formulation Example 3 wettable powder]
Compound of the present invention (10 parts by mass), white carbon (10 parts by mass), polyvinyl alcohol (2 parts by mass), dioctyl sulfosuccinate sodium salt (0.5 parts by mass), alkylbenzenesulfonic acid sodium salt (5 parts by mass), calcining Diatomaceous earth (10 parts by mass) and kaolinite clay (62.5 parts by mass) are sufficiently mixed and pulverized with an air mill to obtain a wettable powder.
　以下、本発明化合物を含有する組成物（農園芸用有害生物防除剤、農園芸用殺菌剤など）の施用について説明する。
　本発明化合物を含有する組成物の施用方法としては、植物体もしくは種子と接触させる方法、または、栽培土壌に含有させて、植物の根もしくは地下茎に接触させる方法が挙げられる。具体例として、組成物の植物個体への茎葉散布処理、注入処理、苗箱処理、セルトレー処理、植物種子への吹き付け処理、植物種子への塗沫処理、植物種子への浸漬処理、植物種子への粉衣処理、土壌表面への散布処理、土壌表面への散布処理後の土壌混和、土壌中への注入処理、土壌中での注入処理後の土壌混和、土壌潅注処理、土壌潅注処理後の土壌混和等が挙げられる。通常、当業者が利用するようないかなる施用方法を用いても十分な効力を発揮する。 Hereinafter, the application of the composition containing the compound of the present invention (a pesticide for agricultural and horticultural use, a fungicide for agricultural and horticultural use, and the like) will be described.
Examples of a method for applying the composition containing the compound of the present invention include a method in which the composition is brought into contact with a plant or a seed, and a method in which the composition is contained in a cultivated soil and brought into contact with a root or a rhizome of a plant. As specific examples, foliage spraying treatment, injection treatment, seedling box treatment, cell tray treatment, spraying treatment on plant seeds, spray treatment on plant seeds, immersion treatment on plant seeds, immersion treatment on plant seeds, on plant seeds of the composition Dressing, spraying on the soil surface, soil mixing after spraying on the soil surface, injection into the soil, soil mixing after injection in the soil, soil irrigation, after soil irrigation Soil mixing and the like. Generally, any method of application as used by those skilled in the art will work well.
　本発明でいう「植物」とは、光合成をして運動せずに生活するものをいう。具体例として、稲、小麦、大麦、トウモロコシ、コーヒー、バナナ、ブドウ、リンゴ、ナシ、モモ、オウトウ、カキ、カンキツ、大豆、インゲン、ワタ、イチゴ、ジャガイモ、キャベツ、レタス、トマト、キュウリ、ナス、スイカ、テンサイ、ホウレンソウ、サヤエンドウ、カボチャ、サトウキビ、タバコ、ピーマン、サツマイモ、サトイモ、コンニャク、綿、ヒマワリ、バラ、チューリップ、キク、芝等およびそれらのＦ１品種等が挙げられる。また、遺伝子等を人工的に操作することにより生み出され、元来自然界に存在するものではない遺伝子組み換え作物も含み、例えば、除草剤耐性を付与した大豆、トウモロコシ、綿等、寒冷地適応したイネ、タバコ等、殺虫物質生産能を付与したトウモロコシ、綿等の農園芸作物等が挙げられる。さらに、マツ、トネリコ、イチョウ、カエデ、カシ、ポプラ、ケヤキ等の樹木等が挙げられる。また、本発明でいう「植物体」とは、前記の植物個体を構成する全ての部位を総称するものであり、例えば、茎、葉、根、種子、花、果実等が挙げられる。 「“ Plant ”as used in the present invention refers to a plant that performs photosynthesis and lives without exercise. Specific examples include rice, wheat, barley, corn, coffee, banana, grape, apple, pear, peach, cherry, oyster, citrus, soybean, bean, cotton, strawberry, potato, cabbage, lettuce, tomato, cucumber, eggplant, Watermelon, sugar beet, spinach, snow pea, pumpkin, sugar cane, tobacco, bell pepper, sweet potato, taro, konjac, cotton, sunflower, rose, tulip, chrysanthemum, turf, etc. and their F1 varieties and the like can be mentioned. It also includes genetically modified crops that are produced by manipulating genes and the like and are not originally present in the natural world. And agricultural and horticultural crops, such as corn and cotton, to which insecticide-producing ability is imparted. Further, trees such as pine, ash, ginkgo, maple, oak, poplar, zelkova and the like can be mentioned. The “plant” in the present invention is a general term for all the parts constituting the above-mentioned plant individual, and includes, for example, stems, leaves, roots, seeds, flowers, fruits and the like.
　本発明でいう「種子」とは、幼植物が発芽するための栄養分を蓄え、農業上繁殖に用いられるものをいう。具体例として、トウモロコシ、大豆、綿、稲、テンサイ、小麦、大麦、ヒマワリ、トマト、キュウリ、ナス、ホウレンソウ、サヤエンドウ、カボチャ、サトウキビ、タバコ、ピーマン、セイヨウアブラナ等の種子、それらのＦ１品種等の種子、サトイモ、ジャガイモ、サツマイモ、コンニャク等の種芋、食用ゆり、チューリップ等の球根、ラッキョウ等の種球、および遺伝子組み換え作物の種子ならびに塊茎等が挙げられる。 「The“ seed ”in the present invention refers to a seed that stores nutrients for germinating young plants and is used for agricultural reproduction. Specific examples include corn, soybean, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, snow peas, pumpkin, sugar cane, tobacco, peppers, oilseed rape and other seeds, and their F1 varieties and the like. Examples include seeds, seed potatoes such as taro, potato, sweet potato, and konjac, edible lilies, bulbs such as tulips, seed balls such as raccoon, and seeds and tubers of genetically modified crops.
　本発明化合物を含有する組成物の施用量および施用濃度は、対象作物、対象病害、病害の発生程度、化合物の剤型、施用方法および各種環境条件等によって変動するが、散布または潅注する場合には、有効成分量としてヘクタール当たり０．１～１０，０００ｇが適当であり、好ましくは、ヘクタール当り１０～１，０００ｇである。また、種子処理の場合の使用量は、有効成分量として種子１ｋｇ当たり０．０００１～１０００ｇであり、好ましくは、０．００１～１００ｇである。本発明化合物を含有する組成物を植物個体への茎葉散布処理、土壌表面への散布処理、土壌中への注入処理または土壌潅注処理として使用する場合は、適当な担体に適当な濃度で希釈した後、処理を行ってもよい。本発明化合物を含有する組成物を植物種子に接触させる場合は、適当な濃度に希釈した後、植物種子に浸漬、粉衣、吹き付けまたは塗沫処理して用いてもよい。浸漬、粉衣、吹き付けまたは塗沫処理する場合の組成物使用量は、通常、有効成分量として、乾燥植物種子重量の０．０５～５０％程度であり、好ましくは、０．１～３０％が適当であるが、組成物の形態や処理対象となる植物種子の種類により適宜設定すればよく、これら範囲に限定されるものではない。 The application rate and application concentration of the composition containing the compound of the present invention vary depending on the target crop, the target disease, the degree of occurrence of the disease, the dosage form of the compound, the application method, and various environmental conditions. The amount of the active ingredient is suitably from 0.1 to 10,000 g per hectare, preferably from 10 to 1,000 g per hectare. In the case of seed treatment, the amount used is 0.0001 to 1000 g, preferably 0.001 to 100 g, per kg of seed as an active ingredient. When the composition containing the compound of the present invention is used as a foliage spraying treatment on a plant individual, a spraying treatment on a soil surface, an injection treatment into soil or a soil irrigation treatment, the composition is diluted with an appropriate carrier at an appropriate concentration. Thereafter, the processing may be performed. When the composition containing the compound of the present invention is brought into contact with a plant seed, it may be diluted to an appropriate concentration and then immersed, dressed, sprayed or smeared on the plant seed before use. The amount of the composition used for immersion, dressing, spraying or smearing is usually about 0.05 to 50%, preferably 0.1 to 30% of the weight of the dried plant seeds as an active ingredient. Is appropriate, but may be appropriately set depending on the form of the composition and the type of plant seed to be treated, and is not limited to these ranges.
　本発明化合物は、必要に応じて他の農薬、例えば、殺菌剤、殺虫剤（殺ダニ剤および殺線虫剤を含む）、除草剤、微生物資材等および植物成長調節剤等の農薬、核酸を有効成分とする病害防除剤（国際公開第２０１４／０６２７７５号）、土壌改良剤または肥効物質等と混合して使用することができる。本発明化合物と他の農薬を混合して使用する方法としては、本発明化合物と他の農薬とを一つの剤型に製剤化して使用する方法、それぞれが別々の剤型に製剤化された両者を使用前に混合して使用する方法、それぞれが別々の剤型に製剤化された両者を同時に使用する方法、または、それぞれが別々の剤型に製剤化された両者について、いずれか一方を使用した後に他方を使用する方法が挙げられる。
　本発明化合物と混合して使用することができる殺菌剤に含まれる具体的な成分は、以下の群ｂで例示され、これらの塩、異性体およびＮ－オキシド体を含む。ただし、公知の殺菌剤はこれらに限定されるものではない。 The compound of the present invention may contain, if necessary, other pesticides, for example, pesticides such as fungicides, insecticides (including acaricides and nematicides), herbicides, microbial materials, and plant growth regulators, and nucleic acids. It can be used as a mixture with a disease control agent (WO 2014/062775), a soil conditioner or a fertilizer as an active ingredient. As a method of mixing and using the compound of the present invention and other pesticides, a method of formulating and using the compound of the present invention and another pesticide in one dosage form, both of which are formulated in separate dosage forms Are used before and after use, either using both formulated in separate dosage forms at the same time, or using both formulated in separate dosage forms. And then use the other.
Specific components contained in the fungicide which can be used by mixing with the compound of the present invention are exemplified by the following group b, and include salts, isomers and N-oxides thereof. However, the known disinfectants are not limited to these.
群ｂ：
ｂ－１：フェニルアミド系殺菌剤
　フェニルアミド系殺菌剤として、［ｂ－１．１］：ベナラキシル（ｂｅｎａｌａｘｙｌ）、［ｂ－１．２］ベナラキシルＭまたはキララキシル（ｂｅｎａｌａｘｙｌ－Ｍまたはｋｉｒａｌａｘｙｌ）、［ｂ－１．３］フララキシル（ｆｕｒａｌａｘｙｌ）、［ｂ－１．４］メタラキシル（ｍｅｔａｌａｘｙｌ）、［ｂ－１．５］メタラキシルＭまたはメフェノキサム（ｍｅｔａｌａｘｙｌ－Ｍまたはｍｅｆｅｎｏｘａｍ）、［ｂ－１．６］オキサジキシル（ｏｘａｄｉｘｙｌ）、［ｂ－１．７］オフラセ（ｏｆｕｒａｃｅ）等が挙げられる。 Group b:
b-1: Phenylamide fungicide As a phenylamide fungicide, [b-1.1]: benalaxyl, [b-1.2] benalaxyl M or chiralaxyl (benalaxyl-M or kiralaxyl), [b [1.3] furalaxyl, [b-1.4] metalaxyl, [b-1.5] metalaxyl M or mefenoxam (metalaxyl-M or mefenoxam), [b-1.6] oxadixyl ( oxadixyl), [b-1.7] offurase, and the like.
ｂ－２：有糸核分裂および細胞分裂阻害剤
　有糸核分裂および細胞分裂阻害剤として、［ｂ－２．１］ベノミル（ｂｅｎｏｍｙｌ）、［ｂ－２．２］カルベンダジム（ｃａｒｂｅｎｄａｚｉｍ）、［ｂ－２．３］フベリダゾール（ｆｕｂｅｒｉｄａｚｏｌｅ）、［ｂ－２．４］チアベンダゾール（ｔｈｉａｂｅｎｄａｚｏｌｅ）、［ｂ－２．５］チオファネート（ｔｈｉｏｐｈａｎａｔｅ）、［ｂ－２．６］チオファネートメチル（ｔｈｉｏｐｈａｎａｔｅ－ｍｅｔｈｙｌ）、［ｂ－２．７］ジエトフェンカルブ（ｄｉｅｔｈｏｆｅｎｃａｒｂ）、［ｂ－２，８］ゾキサミド（ｚｏｘａｍｉｄｅ）、［ｂ－２．９］エタボキサム（ｅｔｈａｂｏｘａｍ）、［ｂ－２．１０］ペンシクロン（ｐｅｎｃｙｃｕｒｏｎ）、［ｂ－２．１１］フルオピコリド（ｆｌｕｏｐｉｃｏｌｉｄｅ）、［ｂ－２．１２］フェナマクリル（ｐｈｅｎａｍａｃｒｉｌ）等が挙げられる。 b-2: Mitotic and mitosis inhibitor [b-2.1] benomyl, [b-2.2] carbendazim, [b- 2.3] Fuberidazole, [b-2.4] thiabendazole, [b-2.5] thiophanate, [b-2.6] thiophanate-methyl, [b- 2.7] Diethofencarb, [b-2,8] Zoxamide, [b-2.9] Ethaboxam, [b-2.10] Pencyclocurn, [b-2. 11] Fluopico Lido (fluopicolide), [b-2.12] phenamacril, and the like.
ｂ－３：コハク酸脱水素酵素阻害剤（ＳＤＨＩ剤）
　コハク酸脱水素酵素阻害剤（ＳＤＨＩ剤）として、［ｂ－３．１］ベノダニル（ｂｅｎｏｄａｎｉｌ）、［ｂ－３．２］ベンゾビンジフルピル（ｂｅｎｚｏｖｉｎｄｉｆｌｕｐｙｒ）、［ｂ－３．３］ビキサフェン（ｂｉｘａｆｅｎ）、［ｂ－３．４］ボスカリド（ｂｏｓｃａｌｉｄ）、［ｂ－３．５］カルボキシン（ｃａｒｂｏｘｉｎ）、［ｂ－３．６］フェンフラム（ｆｅｎｆｕｒａｍ）、［ｂ－３．７］フルオピラム（ｆｌｕｏｐｙｒａｍ）、［ｂ－３．８］フルトラニル（ｆｌｕｔｏｌａｎｉｌ）、［ｂ－３．９］フルキサピロキサド（ｆｌｕｘａｐｙｒｏｘａｄ）、［ｂ－３．１０］フラメトピル（ｆｕｒａｍｅｔｐｙｒ）、［ｂ－３．１１］イソフェタミド（ｉｓｏｆｅｔａｍｉｄ）、［ｂ－３．１２］イソピラザム（ｉｓｏｐｙｒａｚａｍ）、［ｂ－３．１３］メプロニル（ｍｅｐｒｏｎｉｌ）、［ｂ－３．１４］オキシカルボキシン（ｏｘｙｃａｒｂｏｘｉｎ）、［ｂ－３．１５］ペンチオピラド（ｐｅｎｔｈｉｏｐｙｒａｄ）、［ｂ－３．１６］ペンフルフェン（ｐｅｎｆｌｕｆｅｎ）、［ｂ－３．１７］ピジフルメトフェン（ｐｙｄｉｆｌｕｍｅｔｏｆｅｎ）、［ｂ－３．１８］セダキサン（ｓｅｄａｘａｎｅ）、［ｂ－３．１９］チフルザミド（ｔｈｉｆｌｕｚａｍｉｄｅ）、［ｂ－３．２０］ピラジフルミド（ｐｙｒａｚｉｆｌｕｍｉｄ）等が挙げられる。 b-3: succinate dehydrogenase inhibitor (SDHI agent)
As the succinate dehydrogenase inhibitors (SDHI agents), [b-3.1] benodanil, [b-3.2] benzovindiflupyr, [b-3.3] bixafen (bixafen) ), [B-3.4] boscarid, [b-3.5] carboxin, [b-3.6] fenfuram, [b-3.7] fluopyram , [B-3.8] flutolanil, [b-3.9] fluxapyroxad, [b-3.10] furamepyr, [b-3.11] isofetamid ), [B-3.12] isoprazam (isop) razam), [b-3.13] mepronil, [b-3.14] oxycarboxin, [b-3.15] penthiopyrad, [b-3.16] penflufen ( penflufen), [b-3.17] pydiflumetofen, [b-3.18] sedaxane, [b-3.19] thifluzamide, [b-3.20] pyraziflumide (Pyrazifflumid) and the like.
ｂ－４：キノン外部阻害剤（ＱｏＩ剤）
　キノン外部阻害剤（ＱｏＩ剤）として、［ｂ－４．１］アゾキシストロビン（ａｚｏｘｙｓｔｒｏｂｉｎ）、［ｂ－４．２］クモキシストロビン（ｃｏｕｍｏｘｙｓｔｒｏｂｉｎ）、［ｂ－４．３］ジモキシストロビン（ｄｉｍｏｘｙｓｔｒｏｂｉｎ）、［ｂ－４．４］エノキサストロビン（ｅｎｏｘａｓｔｒｏｂｉｎ）、［ｂ－４．５］ファモキサドン（ｆａｍｏｘａｄｏｎｅ）、［ｂ－４．６］フェンアミドン（ｆｅｎａｍｉｄｏｎｅ）、［ｂ－４．７］フェナミンストロビン（ｆｅｎａｍｉｎｓｔｒｏｂｉｎ）、［ｂ－４．８］フルフェノキシストロビン（ｆｌｕｆｅｎｏｘｙｓｔｒｏｂｉｎ）、［ｂ－４．９］フルオキサストロビン（ｆｌｕｏｘａｓｔｒｏｂｉｎ）、［ｂ－４．１０］クレソキシムメチル（ｋｒｅｓｏｘｉｍ－ｍｅｔｈｙｌ）、［ｂ－４．１１］マンデストロビン（ｍａｎｄｅｓｔｒｏｂｉｎ）、［ｂ－４．１２］メトミノストロビン（ｍｅｔｏｍｉｎｏｓｔｒｏｂｉｎ）、［ｂ－４．１３］オリサストロビン（ｏｒｙｓａｓｔｒｏｂｉｎ）、［ｂ－４．１４］ピコキシストロビン（ｐｉｃｏｘｙｓｔｒｏｂｉｎ）、［ｂ－４．１５］ピラクロストロビン（ｐｙｒａｃｌｏｓｔｒｏｂｉｎ）、［ｂ－４．１６］ピラメトストロビン（ｐｙｒａｍｅｔｏｓｔｒｏｂｉｎ）、［ｂ－４．１７］ピラオキシストロビン（ｐｙｒａｏｘｙｓｔｒｏｂｉｎ）、［ｂ－４．１８］ピリベンカルブ（ｐｙｒｉｂｅｎｃａｒｂ）、［ｂ－４．１９］トリクロピリカルブ（ｔｒｉｃｌｏｐｙｒｉｃａｒｂ）、［ｂ－４．２０］トリフロキシストロビン（ｔｒｉｆｌｏｘｙｓｔｒｏｂｉｎ）等が挙げられる。 b-4: Quinone external inhibitor (QoI agent)
[B-4.1] azoxystrobin, [b-4.2] cumoxystrobin, [b-4.3] dimoxyst as quinone external inhibitors (QoI agents) Robin (dimoxystrobin), [b-4.4] enoxastrobin, [b-4.5] Famoxadone, [b-4.6] fenamidone, [b-4.7] Phenaminestrobin, [b-4.8] flufenoxystrobin, [b-4.9] fluoxastrobin, [b-4.10] kresoxim-methyl hyl), [b-4.11] Mandestrobin, [b-4.12] Metominostrobin, [b-4.13] Orysastrobin, [b-4.14] Picoxystrobin, [b-4.15] pyraclostrobin, [b-4.16] pyramethostrobin, [b-4.17] pyraoxystrobin , [B-4.18] pyribencarb, [b-4.19] triclopyricarb, [b-4.20] trifloxystrobin obin), and the like.
ｂ－５：キノン内部阻害剤（ＱｉＩ剤）
　キノン内部阻害剤（ＱｉＩ剤）として、［ｂ－５．１］シアゾファミド（ｃｙａｚｏｆａｍｉｄ）、［ｂ－５．２］アミスルブロム（ａｍｉｓｕｌｂｒｏｍ）等が挙げられる。 b-5: quinone internal inhibitor (QiI agent)
Examples of quinone internal inhibitors (QiI agents) include [b-5.1] cyazofamid, [b-5.2] amisulbrom, and the like.
ｂ－６：酸化的リン酸化脱共役阻害剤
　酸化的リン酸化脱共役阻害剤として、［ｂ－６．１］ビナパクリル（ｂｉｎａｐａｃｒｙｌ）、［ｂ－６．２］メプチルジノカップ（ｍｅｐｔｙｌｄｉｎｏｃａｐ）、［ｂ－６．３］ジノカップ（ｄｉｎｏｃａｐ）、［ｂ－６．４］フルアジナム（ｆｌｕａｚｉｎａｍ）等が挙げられる。 b-6: Oxidative phosphorylation uncoupling inhibitor As the oxidative phosphorylation uncoupling inhibitor, [b-6.1] binapacryl, [b-6.2] meptyldinocap, [b-6.2] [b-6.3] dinocap, [b-6.4] fluazinam and the like.
ｂ－７：キノン外部スチグマテリン結合サブサイト阻害剤（ＱｏＳＩ剤）
　キノン外部スチグマテリン結合サブサイト阻害剤（ＱｏＳＩ剤）として、［ｂ－７．１］アメトクトラジン（ａｍｅｔｏｃｔｒａｄｉｎ）等が挙げられる。 b-7: Quinone external stigmatelin binding subsite inhibitor (QoSI agent)
[B-7.1] amethoctrazine (Q-SI agent) includes quinone external stigmatelin binding subsite inhibitor.
ｂ－８：アミノ酸生合成阻害剤
　アミノ酸生合成阻害剤として、［ｂ－８．１］シプロジニル（ｃｙｐｒｏｄｉｎｉｌ）、［ｂ－８．２］メパニピリム（ｍｅｐａｎｉｐｙｒｉｍ）、［ｂ－８．３］ピリメタニル（ｐｙｒｉｍｅｔｈａｎｉｌ）等が挙げられる。 b-8: amino acid biosynthesis inhibitor [b-8.1] cyprodinil, [b-8.2] mepanipyrim, [b-8.3] pyrimethanil as amino acid biosynthesis inhibitors ) And the like.
ｂ－９：タンパク質生合成阻害剤
　タンパク質生合成阻害剤として、［ｂ－９．１］ストレプトマイシン（ｓｔｒｅｐｔｏｍｙｃｉｎ）、［ｂ－９．２］ブラストサイジンＳ（ｂｌａｓｔｉｃｉｄｉｎ－Ｓ）、［ｂ－９．３］カスガマイシン（ｋａｓｕｇａｍｙｃｉｎ）、［ｂ－９．４］オキシテトラサイクリン（ｏｘｙｔｅｔｒａｃｙｃｌｉｎｅ）等が挙げられる。 b-9: Protein biosynthesis inhibitor As a protein biosynthesis inhibitor, [b-9.1] streptomycin, [b-9.2] blasticidin-S, [b-9. 3] kasugamycin, [b-9.4] oxytetracycline and the like.
ｂ－１０：シグナル伝達阻害剤
　シグナル伝達阻害剤として、［ｂ－１０．１］フェンピクロニル（ｆｅｎｐｉｃｌｏｎｉｌ）、［ｂ－１０．２］フルジオキソニル（ｆｌｕｄｉｏｘｏｎｉｌ）、［ｂ－１０．３］キノキシフェン（ｑｕｉｎｏｘｙｆｅｎ）、［ｂ－１０．４］プロキナジド（ｐｒｏｑｕｉｎａｚｉｄ）、［ｂ－１０．５］クロゾリネート（ｃｈｌｏｚｏｌｉｎａｔｅ）、［ｂ－１０．６］ジメタクロン（ｄｉｍｅｔｈａｃｈｌｏｎｅ）、［ｂ－１０．７］イプロジオン（ｉｐｒｏｄｉｏｎｅ）、［ｂ－１０．８］プロシミドン（ｐｒｏｃｙｍｉｄｏｎｅ）、［ｂ－１０．９］ビンクロゾリン（ｖｉｎｃｌｏｚｏｌｉｎ）等が挙げられる。 b-10: Signaling inhibitor As a signalling inhibitor, [b-10.1] fenpiclonil, [b-10.2] fludioxonil, [b-10.3] quinoxyfen, [B-10.4] proquinazide, [b-10.5] clozolinate, [b-10.6] dimethaclone, [b-10.7] iprodione, [b] -10.8] procymidone, [b-10.9] vinclozolin, and the like.
ｂ－１１：脂質および細胞膜生合成阻害剤
　脂質および細胞膜生合成阻害剤として、［ｂ－１１．１］エジフェンホス（ｅｄｉｆｅｎｐｈｏｓ）、［ｂ－１１．２］イプロベンホス（ｉｐｒｏｂｅｎｆｏｓ）、［ｂ－１１．３］ピラゾホス（ｐｙｒａｚｏｐｈｏｓ）、［ｂ－１１．４］イソプロチオラン（ｉｓｏｐｒｏｔｈｉｏｌａｎｅ）、［ｂ－１１．５］ビフェニル（ｂｉｐｈｅｎｙｌ）、［ｂ－１１．６］クロロネブ（ｃｈｌｏｒｏｎｅｂ）、［ｂ－１１．７］ジクロラン（ｄｉｃｌｏｒａｎ）、［ｂ－１１．８］キントゼン（ｑｕｉｎｔｏｚｅｎｅ）、［ｂ－１１．９］テクナゼン（ｔｅｃｎａｚｅｎｅ）、［ｂ－１１．１０］トルクロホスメチル（ｔｏｌｃｌｏｆｏｓ－ｍｅｔｈｙｌ）、［ｂ－１１．１１］エトリジアゾール（ｅｃｈｌｏｍｅｚｏｌ　ｏｒ　ｅｔｒｉｄｉａｚｏｌｅ）、［ｂ－１１．１２］ヨードカルブ（ｉｏｄｏｃａｒｂ）、［ｂ－１１．１３］プロパモカルブ（ｐｒｏｐａｍｏｃａｒｂ）、［ｂ－１１．１４］プロチオカルブ（ｐｒｏｔｈｉｏｃａｒｂ）等が挙げられる。 b-11: Lipid and cell membrane biosynthesis inhibitors As lipids and cell membrane biosynthesis inhibitors, [b-11.1] edifenphos, [b-11.2] iprobenfos, [b-11. 3] ] Pyrazophos, [b-11.4] isoprothiolane, [b-11.5] biphenyl, [b-11.6] chloroneb, [b-11.7] dichlorane (Dicloran), [b-11.8] quintogene, [b-11. 9] technagene, [b-11.10] tolclofos-methyl, [b-11.11] Etridiazole (ec hlomezol or etradidiazole, [b-11.12] iodocarb, [b-11.13] propamocarb, [b-11.14] prothiocarb, and the like.
ｂ－１２：脱メチル化阻害剤（ＤＭＩ剤）
　脱メチル化阻害剤（ＤＭＩ剤）として、［ｂ－１２．１］アザコナゾール（ａｚａｃｏｎａｚｏｌｅ）、［ｂ－１２．２］ビテルタノール（ｂｉｔｅｒｔａｎｏｌ）、［ｂ－１２．３］ブロムコナゾール（ｂｒｏｍｕｃｏｎａｚｏｌｅ）、［ｂ－１２．４］シプロコナゾール（ｃｙｐｒｏｃｏｎａｚｏｌｅ）、［ｂ－１２．５］ジフェノコナゾール（ｄｉｆｅｎｏｃｏｎａｚｏｌｅ）、［ｂ－１２．６］ジニコナゾール（ｄｉｎｉｃｏｎａｚｏｌｅ）、［ｂ－１２．７］ジニコナゾールＭ（ｄｉｎｉｃｏｎａｚｏｌｅ－Ｍ）、［ｂ－１２．８］エポキシコナゾール（ｅｐｏｘｉｃｏｎａｚｏｌｅ）、［ｂ－１２．９］エタコナゾール（ｅｔａｃｏｎａｚｏｌｅ）、［ｂ－１２．１０］フェナリモル（ｆｅｎａｒｉｍｏｌ）、［ｂ－１２．１１］フェンブコナゾール（ｆｅｎｂｕｃｏｎａｚｏｌｅ）、［ｂ－１２．１２］フルキンコナゾール（ｆｌｕｑｕｉｎｃｏｎａｚｏｌｅ）、［ｂ－１２．１３］キンコナゾール（ｑｕｉｎｃｏｎａｚｏｌｅ）、［ｂ－１２．１４］フルシラゾール（ｆｌｕｓｉｌａｚｏｌｅ）、［ｂ－１２．１５］フルトリアホール（ｆｌｕｔｒｉａｆｏｌ）、［ｂ－１２．１６］ヘキサコナゾール（ｈｅｘａｃｏｎａｚｏｌｅ）、［ｂ－１２．１７］イマザリル（ｉｍａｚａｌｉｌ）、［ｂ－１２．１８］イミベンコナゾール（ｉｍｉｂｅｎｃｏｎａｚｏｌｅ）、［ｂ－１２．１９］イプコナゾール（ｉｐｃｏｎａｚｏｌｅ）、［ｂ－１２．２０］メトコナゾール（ｍｅｔｃｏｎａｚｏｌｅ）、［ｂ－１２．２１］ミクロブタニル（ｍｙｃｌｏｂｕｔａｎｉｌ）、［ｂ－１２．２２］ヌアリモール（ｎｕａｒｉｍｏｌ）、［ｂ－１２．２３］オキスポコナゾール（ｏｘｐｏｃｏｎａｚｏｌｅ）、［ｂ－１２．２４］オキスポコナゾールフマル酸塩（ｏｘｐｏｃｏｎａｚｏｌｅ　ｆｕｍａｒａｔｅ）、［ｂ－１２．２５］ペフラゾエート（ｐｅｆｕｒａｚｏａｔｅ）、［ｂ－１２．２６］ペンコナゾール（ｐｅｎｃｏｎａｚｏｌｅ）、［ｂ－１２．２７］プロクロラズ（ｐｒｏｃｈｌｏｒａｚ）、［ｂ－１２．２８］プロピコナゾール（ｐｒｏｐｉｃｏｎａｚｏｌｅ）、［ｂ－１２．２９］プロチオコナゾール（ｐｒｏｔｈｉｏｃｏｎａｚｏｌｅ）、［ｂ－１２．３０］ピリフェノックス（ｐｙｒｉｆｅｎｏｘ）、［ｂ－１２．３１］ピリソキサゾール（ｐｙｒｉｓｏｘａｚｏｌｅ）、［ｂ－１２．３２］シメコナゾール（ｓｉｍｅｃｏｎａｚｏｌｅ）、［ｂ－１２．３３］テブコナゾール（ｔｅｂｕｃｏｎａｚｏｌｅ）、［ｂ－１２．３４］テトラコナゾール（ｔｅｔｒａｃｏｎａｚｏｌｅ）、［ｂ－１２．３５］トリアジメホン（ｔｒｉａｄｉｍｅｆｏｎ）、［ｂ－１２．３６］トリアジメノール（ｔｒｉａｄｉｍｅｎｏｌ）、［ｂ－１２．３７］トリフルミゾール（ｔｒｉｆｌｕｍｉｚｏｌｅ）、［ｂ－１２．３８］トリホリン（ｔｒｉｆｏｒｉｎｅ）、［ｂ－１２．３９］トリチコナゾール（ｔｒｉｔｉｃｏｎａｚｏｌｅ）［ｂ－１２．４０］メフェントリフルコナゾール（ｍｅｆｅｎｔｒｉｆｌｕｃｏｎａｚｏｌｅ）、［ｂ－１２．４１］イプフェントリフルコナゾール（ｉｐｆｅｎｔｒｉｆｌｕｃｏｎａｚｏｌｅ）等が挙げられる。 b-12: Demethylation inhibitor (DMI agent)
As demethylation inhibitors (DMI agents), [b-12. 1] azaconazole, [b-12. 2] bitertanol, [b-12. 3] bromuconazole, [b-12. b-12.4] cyproconazole, [b-12.5] difenoconazole, [b-12.6] diconizazole, [b-12.7] diconizazole-M ), [B-12.8] epoxyconazole, [b-12.9] etaconazole, [b-12.10] fenarimol, [b-12.11] Fenbuconazole, [b-12.12] fluquinconazole, [b-12.13] quinconazole, [b-12.14] flusilazole, [b-12] .15] flutriafol, [b-12.16] hexaconazole, [b-12.17] imazalil, [b-12.18] imibenconazole, [B-12.19] ipconazole, [b-12.20] metconazole, [b-12.21] microbutanil , [B-12.22] nuarimol, [b-12.23] oxpoconazole, [b-12.24] oxpoconazole fumarate, [b- 12.25] pefurazoate, [b-12.26] penconazole, [b-12.27] prochloraz, [b-12.28] propiconazole, [b- 12.29] prothioconazole, [b-12.30] pyrifenox, [b-12.31] pyrisoxazole, [b-12.32]. Simeconazole, [b-12.33] tebuconazole, [b-12.34] tetraconazole, [b-12.35] triadimefon, [b-12.36] Triadimenol, [b-12.37] triflumizole, [b-12.38] triforine, [b-12.39] triticonazole [b-12] .40] mefentrifluconazole, [b-12.41] ipfentrifluconazole, and the like.
ｂ－１３：アミン系殺菌剤
　アミン系殺菌剤として、［ｂ－１３．１］アルジモルフ（ａｌｄｉｍｏｒｐｈ）、［ｂ－１３．２］ドデモルフ（ｄｏｄｅｍｏｒｐｈ）、［ｂ－１３．３］フェンプロピモルフ（ｆｅｎｐｒｏｐｉｍｏｒｐｈ）、［ｂ－１３．４］トリデモルフ（ｔｒｉｄｅｍｏｒｐｈ）、［ｂ－１３．５］フェンプロピジン（ｆｅｎｐｒｏｐｉｄｉｎ）、［ｂ－１３．６］ピペラリン（ｐｉｐｅｒａｌｉｎ）、［ｂ－１３．７］スピロキサミン（ｓｐｉｒｏｘａｍｉｎｅ）等が挙げられる。 b-13: Amine-based fungicide As an amine-based fungicide, [b-13.1] aldimorph, [b-13.2] dodemorph, [b-13.3] fenpropimorph ), [B-13.4] tridemorph, [b-13.5] fenpropidin, [b-13.6] piperaline, [b-13.7] spiroxamine ) And the like.
ｂ－１４：ステロール生合成のＣ４位脱メチル化における３－ケト還元酵素阻害剤
　ステロール生合成のＣ４位脱メチル化における３－ケト還元酵素阻害剤として、［ｂ－１４．１］フェンヘキサミド（ｆｅｎｈｅｘａｍｉｄ）、［ｂ－１４．２］フェンピラザミン（ｆｅｎｐｙｒａｚａｍｉｎｅ）等が挙げられる。 b-14: 3-keto reductase inhibitor in C4-position demethylation of sterol biosynthesis [b-14.1] fenhexamide as 3-keto-reductase inhibitor in C4-position demethylation of sterol biosynthesis (Fenhexamid), [b-14.2] fenpyrazamine and the like.
ｂ－１５：ステロール生合成のスクアレンエポキシダーゼ阻害剤
　ステロール生合成のスクアレンエポキシダーゼ阻害剤として、［ｂ－１５．１］ピリブチカルブ（ｐｙｒｉｂｕｔｉｃａｒｂ）、［ｂ－１５．２］ナフチフィン（ｎａｆｔｉｆｉｎｅ）、［ｂ－１５．３］テルビナフィン（ｔｅｒｂｉｎａｆｉｎｅ）等が挙げられる。 b-15: Squalene epoxidase inhibitor for sterol biosynthesis As a squalene epoxidase inhibitor for sterol biosynthesis, [b-15.1] pyributicarb, [b-15.2] naftifine, [b -15.3] terbinafine and the like.
ｂ－１６：細胞壁生合成阻害剤
　細胞壁生合成阻害剤として、［ｂ－１６．１］ポリオキシン類（ｐｏｌｙｏｘｉｎｓ）、［ｂ－１６．２］ジメトモルフ（ｄｉｍｅｔｈｏｍｏｒｐｈ）、［ｂ－１６．３］フルモルフ（ｆｌｕｍｏｒｐｈ）、［ｂ－１６．４］ピリモルフ（ｐｙｒｉｍｏｒｐｈ）、［ｂ－１６．５］ベンチアバリカルブ（ｂｅｎｔｈｉａｖａｌｉｃａｒｂ）、［ｂ－１６．６］ベンチアバリカルブイソプロピル（ｂｅｎｔｈｉｖａｌｉｃａｒｂ－ｉｓｏｐｒｏｐｙｌ）、［ｂ－１６．７］イプロバリカルブ（ｉｐｒｏｖａｌｉｃａｒｂ）、［ｂ－１６．８］マンジプロパミド（ｍａｎｄｉｐｒｏｐａｍｉｄ）、［ｂ－１７．９］バリフェナレート（ｖａｌｉｆｅｎａｌａｔｅ）等が挙げられる。 b-16: Cell wall biosynthesis inhibitor As a cell wall biosynthesis inhibitor, [b-16.1] polyoxins, [b-16.2] dimethomorph, [b-16.3] flumorph ( flumorph), [b-16.4] pyrimorph, [b-16.5] benthiavalicarb, [b-16.6] bentivaricarb-isopropyl, [b -16.7] iprovalicarb, [b-16.8] mandipropamide, [b-17.9] varifenalate, and the like.
ｂ－１７：メラニン生合成阻害剤
　メラニン生合成阻害剤として、［ｂ－１７．１］フサライド（ｐｈｔｈａｌｉｄｅ　ｏｒ　ｆｔｈａｌｉｄｅ）、［ｂ－１７．２］ピロキロン（ｐｙｒｏｑｕｉｌｏｎｅ）、［ｂ－１７．３］トリシクラゾール（ｔｒｉｃｙｃｌａｚｏｌｅ）、［ｂ－１７．４］カルプロパミド（ｃａｒｐｒｏｐａｍｉｄ）、［ｂ－１７．５］ジクロシメット（ｄｉｃｌｏｃｙｍｅｔ）、［ｂ－１７．６］フェノキサニル（ｆｅｎｏｘａｎｉｌ）、［ｂ－１７．７］トルプロカルブ（ｔｏｌｐｒｏｃａｒｂ）等が挙げられる。 b-17: melanin biosynthesis inhibitor As a melanin biosynthesis inhibitor, [b-17.1] fthalide (phthalide or phthalide), [b-17.2] pyroquilone, [b-17.3] tricyclazole (Triclazole), [b-17.4] carpropamide, [b-17.5] diclocymet, [b-17.6] fenoxanil, [b-17.7] tolprocarb (tolprocarb) ) And the like.
ｂ－１８：宿主植物抵抗性誘導剤
　宿主植物抵抗性誘導剤として、［ｂ－１８．１］アシベンゾラルＳメチル（ａｃｉｂｅｎｚｏｌａｒ－Ｓ－ｍｅｔｈｙｌ）、［ｂ－１８．２］プロベナゾール（ｐｒｏｂｅｎａｚｏｌｅ）、［ｂ－１８．３］チアジニル（ｔｉａｄｉｎｉｌ）、［ｂ－１８．４］イソチアニル（ｉｓｏｔｉａｎｉｌ）、［ｂ－１８．５］ラミナリン（ｌａｍｉｎａｒｉｎ）等が挙げられる。 b-18: Host plant resistance inducer As host plant resistance inducer, [b-18.1] acibenzolar-S-methyl, [b-18.2] probenazole, [b] -18.3] thiadinil, [b-18.4] isotianil, [b-18.5] laminarin, and the like.
ｂ－１９：ジチオカーバメート系殺菌剤
　ジチオカーバメート系殺菌剤として、［ｂ－１９．１］マンコゼブまたはマンゼブ（ｍａｎｃｏｚｅｂ　ｏｒ　ｍａｎｚｅｂ）、［ｂ－１９．２］マンネブ（ｍａｎｅｂ）、［ｂ－１９．３］メチラム（ｍｅｔｉｒａｍ）、［ｂ－１９．４］プロピネブ（ｐｒｏｐｉｎｅｂ）、［ｂ－１９．５］チウラム（ｔｈｉｒａｍ）、［ｂ－１９．６］ジネブ（ｚｉｎｅｂ）、［ｂ－１９．７］ジラム（ｚｉｒａｍ）、［ｂ－１９．８］フェルバム（ｆｅｒｂａｍ）等が挙げられる。 b-19: Dithiocarbamate fungicide [b-19.1] Mancozeb or manzeb (mancozeb or manzeb), [b-19.2] Maneb (maneb), [b-19.3] Methiram, [b-19.4] propineb, [b-19.5] thiuram, [b-19.6] zineb, [b-19.7] ziram (Ziram), [b-19.8] ferbam and the like.
ｂ－２０：フタルイミド系殺菌剤
　フタルイミド系殺菌剤として、［ｂ－２０．１］キャプタン（ｃａｐｔａｎ）、［ｂ－２０．２］キャプタホール（ｃａｐｔａｆｏｌ）、［ｂ－２０．３］ホルペット（ｆｏｌｐｅｔ）、［ｂ－２０．４］フルオロホルペット（ｆｌｕｏｒｏｆｏｌｐｅｔ）等が挙げられる。 b-20: Phthalimide fungicide [b-20.1] captan, [b-20.2] captafol, [b-20.3] folpet (folpet) ), [B-20.4] fluorophorpet and the like.
ｂ－２１：グアニジン系殺菌剤
　グアニジン系殺菌剤として、［ｂ－２１．１］グアザチン（ｇｕａｚａｔｉｎｅ）、［ｂ－２１．２］イミノクタジン（ｉｍｉｎｏｃｔａｄｉｎｅ）、［ｂ－２１．３］イミノクタジンアルベシル酸塩（ｉｍｉｎｏｃｔａｄｉｎｅ　ａｌｂｅｓｉｌａｔｅ）、［ｂ－２１．４］イミノクタジン三酢酸塩（ｉｍｉｎｏｃｔａｄｉｎｅ　ｔｒｉａｃｅｔａｔｅ）等が挙げられる。 b-21: Guanidine fungicide As a guanidine fungicide, [b-21.1] guazatine, [b-21.2] iminoctadine, [b-21.3] iminoctadine albesilate (Iminoctadine albesilate), [b-21.4] iminoctadine triacetate and the like.
ｂ－２２：多作用点接触活性型殺菌剤
　多作用点接触活性型殺菌剤として、［ｂ－２２．１］塩基性塩化銅（ｃｏｐｐｅｒ　ｏｘｙｃｈｌｏｒｉｄｅ）、［ｂ－２２．２］水酸化第二銅（ｃｏｐｐｅｒ（ＩＩ）　ｈｙｄｒｏｘｉｄｅ）、［ｂ－２２．３］塩基性硫酸銅（ｃｏｐｐｅｒ　ｈｙｄｒｏｘｉｄｅ　ｓｕｌｆａｔｅ）、［ｂ－２２．４］有機銅化合物（ｏｒｇａｎｏｃｏｐｐｅｒ　ｃｏｍｐｏｕｎｄ）、［ｂ－２２．５］ドデシルベンゼンスルホン酸ビスエチレンジアミン銅錯塩［ＩＩ］（Ｄｏｄｅｃｙｌｂｅｎｚｅｎｅｓｕｌｐｈｏｎｉｃ　ａｃｉｄ　ｂｉｓｅｔｈｙｌｅｎｅｄｉａｍｉｎｅ　ｃｏｐｐｅｒ　［ＩＩ］　ｓａｌｔ、ＤＢＥＤＣ）、［ｂ－２２．６］硫黄（ｓｕｌｐｈｕｒ）、［ｂ－２２．７］フルオルイミド（ｆｌｕｏｒｏｉｍｉｄｅ）、［ｂ－２２．８］クロロタロニル（ｃｈｌｏｒｏｔｈａｌｏｎｉｌ）、［ｂ－２２．９］ジクロフルアニド（ｄｉｃｈｌｏｆｌｕａｎｉｄ）、［ｂ－２２．１０］トリルフルアニド（ｔｏｌｙｌｆｌｕａｎｉｄ）、［ｂ－２２．１１］アニラジン（ａｎｉｌａｚｉｎｅ）、［ｂ－２２．１２］ジチアノン（ｄｉｔｈｉａｎｏｎ）、［ｂ－２２．１３］キノメチオナート（ｃｈｉｎｏｍｅｔｈｉｏｎａｔ　ｏｒ　ｑｕｉｎｏｍｅｔｈｉｏｎａｔｅ）、［ｂ－２２．１４］ハウチワマメ苗木の子葉からの抽出物（ＢＬＡＤ）等が挙げられる。 b-22: Multi-acting point contact active fungicide [b-22.1] Basic copper chloride (copper oxychloride), [b-22.2] Cupric hydroxide as multi-acting point contact active fungicide (Copper (II) hydroxide), [b-22.3] basic copper sulfate, [b-22.4] organocopper compound, [b-22.5] dodecylbenzene sulfone Acid bisethylenediamine copper complex [II] (Dodecylbenzenesulphonic acid bisethylenediamine copper [II] salt, DBEDC), [b-22.6] sulfur, [b-22.7] fluoroimide de), [b-22.8] chlorothalonil, [b-22.9] dichlofluanid, [b-22.10] tolylfluanid, [b-22.11] Anilazine, [b-22.12] dithianon, [b-22.13] quinomethionate or quinomethionate, [b-22.14] Extract from cotyledon of birch seedling (BLAD), etc. Is mentioned.
ｂ－２３：その他の殺菌剤
　その他の殺菌剤として、［ｂ－２３．１］ジクロベンチアゾクス（ｄｉｃｈｌｏｂｅｎｔｉａｚｏｘ）、［ｂ－２３．２］フェンピコキサミド（ｆｅｎｐｉｃｏｘａｍｉｄ）、［ｂ－２３．３］ジピメチトロン（ｄｉｐｙｍｅｔｉｔｒｏｎｅ）、［ｂ－２３．４］ブピリメート（ｂｕｐｉｒｉｍａｔｅ）、［ｂ－２３．５］ジメチリモール（ｄｉｍｅｔｈｉｒｉｍｏｌ）、［ｂ－２３．６］エチリモール（ｅｔｈｉｒｉｍｏｌ）、［ｂ－２３．７］酢酸トリフェニルスズ（ｆｅｎｔｉｎ　ａｃｅｔａｔｅ）、［ｂ－２３．８］塩化トリフェニルスズ（ｆｅｎｔｉｎ　ｃｈｌｏｒｉｄｅ）、［ｂ－２３．９］水酸化トリフェニルスズ（ｆｅｎｔｉｎ　ｈｙｄｒｏｘｉｄｅ）、［ｂ－２３．１０］オキソリニック酸（ｏｘｏｌｉｎｉｃ　ａｃｉｄ）、［ｂ－２３．１１］ヒメキサゾール（ｈｙｍｅｘａｚｏｌ）、［ｂ－２３．１２］オクチリノン（ｏｃｔｈｉｌｉｎｏｎｅ）、［ｂ－２３．１３］ホセチル（ｆｏｓｅｔｙｌ）、［ｂ－２３．１４］亜リン酸（ｐｈｏｓｐｈｏｒｏｕｓ　ａｃｉｄ）、［ｂ－２３．１５］亜リン酸のナトリウム塩（ｓｏｄｉｕｍ　ｐｈｏｓｐｈｉｔｅ）、［ｂ－２３．１６］亜リン酸のアンモニウム塩（ａｍｍｏｎｉｕｍ　ｐｈｏｓｐｈｉｔｅ）、［ｂ－２３．１７］亜リン酸のカリウム塩（ｐｏｔａｓｓｉｕｍ　ｐｈｏｓｐｈｉｔｅ）、［ｂ－２３．１８］テクロフタラム（ｔｅｃｌｏｆｔａｌａｍ）、［ｂ－２３．１９］トリアゾキシド（ｔｒｉａｚｏｘｉｄｅ）、［ｂ－２３．２０］フルスルファミド（ｆｌｕｓｕｌｆａｍｉｄｅ）、［ｂ－２３．２１］ジクロメジン（ｄｉｃｌｏｍｅｚｉｎｅ）、［ｂ－２３．２２］シルチオファム（ｓｉｌｔｈｉｏｆａｍ）、［ｂ－２３．２３］ジフルメトリム（ｄｉｆｌｕｍｅｔｏｒｉｍ）、［ｂ－２３．２４］メタスルホカルブ（ｍｅｔｈａｓｕｌｆｏｃａｒｂ）、［ｂ－２３．２５］シフルフェナミド（ｃｙｆｌｕｆｅｎａｍｉｄ）、［ｂ－２３．２６］メトラフェノン（ｍｅｔｒａｆｅｎｏｎｅ）、［ｂ－２３．２７］ピリオフェノン（ｐｙｒｉｏｆｅｎｏｎｅ）、［ｂ－２３．２８］ドジン（ｄｏｄｉｎｅ）、［ｂ－２３．２９］フルチアニル（ｆｌｕｔｉａｎｉｌ）、［ｂ－２３．３０］フェリムゾン（ｆｅｒｉｍｚｏｎｅ）、［ｂ－２３．３１］オキサチアピプロリン（ｏｘａｔｈｉａｐｉｐｒｏｌｉｎ）、［ｂ－２３．３２］テブフロキン（ｔｅｂｕｆｌｏｑｕｉｎ）、［ｂ－２３．３３］ピカルブトラゾクス（ｐｉｃａｒｂｕｔｒａｚｏｘ）、［ｂ－２３．３４］バリダマイシン類（ｖａｌｉｄａｍｙｃｉｎｓ）、［ｂ－２３．３５］シモキサニル（ｃｙｍｏｘａｎｉｌ）、［ｂ－２３．３６］キノフメリン（ｑｕｉｎｏｆｕｍｅｌｉｎ）、 b-23: Other fungicides [b-23.1] dichlobentiazox, [b-23.2] fenpicoxamide, [b-23.3] ] Dipymetitron, [b-23.4] bupirimate, [b-23.5] dimethylimol, [b-23.6] ethirimol, [b-23.7] acetic acid Triphenyltin (fentin acetate), [b-23.8] triphenyltin chloride (fentin chloride), [b-23.9] triphenyltin hydroxide (fentin hydroxide), [b-23.10] oxolinic acid (Oxo linic acid), [b-23.11] hymexazol, [b-23.12] octilinone, [b-23.13] fosetyl, [b-23.14] phosphorous acid (Phosphorous acid), [b-23.15] sodium salt of phosphorous acid (sodium phosphite), [b-23.16] ammonium salt of phosphorous acid (ammonium phosphate), [b-23.17] phosphorous acid Potassium salt of acid (potassium phosphate), [b-23.18] teclophthalam, [b-23.19] triazoxide, [b-23.20] flusulfamide [B-23.21] diclomezine, [b-23.22] silthiofam, [b-23.23] diflumetorim, [b-23.24] metasulfocarb, [B-23.25] cyflufenamide, [b-23.26] metrafenone, [b-23.27] pyriophenone, [b-23.28] dodine, [b -23.29] flutianil, [b-23.30] ferimzone, [b-23.31] oxathiapiprolin, [b-23. 32] tebufloquine, [b-23.33] picarbutrazox, [b-23.34] validamycins, [b-23.35] simoxanil, [b- 23.36] quinofumelin,
［ｂ－２３．３７］式（ｓ１）
Figure JPOXMLDOC01-appb-C000080
で表される化合物（国際公開第９８／０４６６０７号参照）、 [B-23.37] Equation (s1)
Figure JPOXMLDOC01-appb-C000080
(See WO 98/046607),
［ｂ－２３．３８］式（ｓ２）
Figure JPOXMLDOC01-appb-C000081
で表される化合物（国際公開第０８／１４８５７０号参照）、 [B-23.38] Equation (s2)
Figure JPOXMLDOC01-appb-C000081
(See WO 08/148570),
［ｂ－２３．３９］式（ｓ３）
Figure JPOXMLDOC01-appb-C000082
で表される化合物（国際公開第９２／０１２９７０号参照）、 [B-23.39] Formula (s3)
Figure JPOXMLDOC01-appb-C000082
(See WO 92/012970),
［ｂ－２３．４０］式（ｓ４）
Figure JPOXMLDOC01-appb-C000083
で表される化合物（国際公開第１２／０８４８１２号参照）、 [B-23.40] Equation (s4)
Figure JPOXMLDOC01-appb-C000083
A compound represented by the following formula (see International Publication No. 12/084812):
［ｂ－２３．４１］式（ｓ５）
Figure JPOXMLDOC01-appb-C000084
で表される化合物（ｇｏｕｇｅｒｏｔｉｎ）、 [B-23.41] Equation (s5)
Figure JPOXMLDOC01-appb-C000084
A compound (gougerotin) represented by
［ｂ－２３．４２］式（ｓ６）
Figure JPOXMLDOC01-appb-C000085
で表される化合物（ｎｉｎｇｎａｎｍｙｃｉｎ）、 [B-23.42] Equation (s6)
Figure JPOXMLDOC01-appb-C000085
A compound (ningnanmycin) represented by:
［ｂ－２３．４３］式（ｓ７）
Figure JPOXMLDOC01-appb-C000086
で表される化合物（国際公開第１０／１３６４７５号参照）、 [B-23.43] Equation (s7)
Figure JPOXMLDOC01-appb-C000086
(See WO 10/136475),
［ｂ－２３．４４］式（ｓ８）
Figure JPOXMLDOC01-appb-C000087
で表される化合物（国際公開第１４／０１０７３７号参照）、 [B-23.44] Equation (s8)
Figure JPOXMLDOC01-appb-C000087
(See WO 14/010737),
［ｂ－２３．４５］式（ｓ９）
Figure JPOXMLDOC01-appb-C000088
で表される化合物（国際公開第１１／０８５０８４号参照）、 [B-23.45] Equation (s9)
Figure JPOXMLDOC01-appb-C000088
(See WO 11/085084),
［ｂ－２３．４６］式（ｓ１０）
Figure JPOXMLDOC01-appb-C000089
で表される化合物（国際公開第１１／１３７００２号参照）、 [B-23.46] Equation (s10)
Figure JPOXMLDOC01-appb-C000089
(See WO 11/137002),
［ｂ－２３．４７］式（ｓ１１）
Figure JPOXMLDOC01-appb-C000090
で表される化合物（国際公開第１３／１６２０７２号参照）、 [B-23.47] Equation (s11)
Figure JPOXMLDOC01-appb-C000090
(See WO 13/162072),
［ｂ－２３．４８］式（ｓ１２）
Figure JPOXMLDOC01-appb-C000091
で表される化合物（国際公開第０８／１１０３１３号参照）、 [B-23.48] Equation (s12)
Figure JPOXMLDOC01-appb-C000091
(See WO 08/110313),
［ｂ－２３．４９］式（ｓ１３）
Figure JPOXMLDOC01-appb-C000092
で表される化合物（国際公開第０９／１５６０９８号参照）、 [B-23.49] Equation (s13)
Figure JPOXMLDOC01-appb-C000092
(See WO09 / 156098),
［ｂ－２３．５０］式（ｓ１４）
Figure JPOXMLDOC01-appb-C000093
で表される化合物（国際公開第１２／０２５５５７号参照）、 [B-23.50] Equation (s14)
Figure JPOXMLDOC01-appb-C000093
(See WO 12/025557),
［ｂ－２３．５１］式（ｓ１５）
Figure JPOXMLDOC01-appb-C000094
で表される化合物（国際公開第１４／００６９４５号参照）、 [B-23.51] Formula (s15)
Figure JPOXMLDOC01-appb-C000094
(See WO 14/006945),
［ｂ－２３．５２］式（ｓ１６）
Figure JPOXMLDOC01-appb-C000095
［式中、Ａ３は、水素原子、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはシアノ基を表し、Ａ４は、水素原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。］で表される化合物（国際公開第１４／０９５６７５号参照）、 [B-23.52] Equation (s16)
Figure JPOXMLDOC01-appb-C000095
[In the formula, A3 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a cyano group, and A4 represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 Represents a haloalkyl group or a C3-C8 cycloalkyl group. (See WO 14/095675),
［ｂ－２３．５３］式（ｓ１７）
Figure JPOXMLDOC01-appb-C000096
［式中、ｍ１は、０～３の整数を表し、Ａ５およびＡ６は、それぞれ独立していて、ハロゲン原子、またはＣ１～Ｃ６のアルキル基を表し、Ａ７およびＡ８は、それぞれ独立していて、ハロゲン原子、またはＣ１～Ｃ６のアルコキシ基を表し、ｍ１が２以上の場合、２以上のＡ７は、それぞれ独立した置換基を表し、同一または異なっていてよい。］で表される化合物（国際公開第０９／１３７５３８号、国際特許第０９／１３７６５１号参照）、 [B-23.53] Equation (s17)
Figure JPOXMLDOC01-appb-C000096
[Wherein, m1 represents an integer of 0 to 3, A5 and A6 each independently represent a halogen atom or a C1 to C6 alkyl group, A7 and A8 each independently represent Represents a halogen atom or a C1 to C6 alkoxy group, and when m1 is 2 or more, two or more A7s each represent an independent substituent, which may be the same or different. (See WO09 / 137538 and WO09 / 137651),
［ｂ－２３．５４］式（ｓ１８）
Figure JPOXMLDOC01-appb-C000097
［式中、Ａ９およびＡ１０は、それぞれ独立していて、水素原子、またはハロゲン原子を表し、Ａ１１は、ハロゲン原子を表し、Ａ１２は、ハロゲン原子、またはＣ１～Ｃ６のアルキル基を表し、Ａ１３は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のアルコキシ基を表す。］で表される化合物（国際公開第１２／０３１０６１号参照）、 [B-23.54] Equation (s18)
Figure JPOXMLDOC01-appb-C000097
[Wherein A9 and A10 are each independently a hydrogen atom or a halogen atom, A11 represents a halogen atom, A12 represents a halogen atom or an alkyl group of C1 to C6, and A13 represents , A halogen atom, a cyano group, a C1-C6 alkyl group, or a C1-C6 alkoxy group. (See WO 12/031061),
［ｂ－２３．５５］式（ｓ１９）
Figure JPOXMLDOC01-appb-C000098
［式中、ｍ２は、０～６の整数を表し、Ａ１４およびＡ１５は、それぞれ独立していて、ハロゲン原子、シアノ基、またはＣ１～Ｃ６のアルキル基を表し、Ａ１６は、水素原子、ハロゲン原子、またはＣ１～Ｃ６のアルコキシ基を表し、Ａ１７は、ハロゲン原子、またはＣ１～Ｃ６のアルコキシ基を表し、ｍ２が２以上の場合、２以上のＡ１７は、それぞれ独立した置換基を表し、同一または異なっていてよい。］で表される化合物（国際公開第０５／１２１１０４号参照）、 [B-23.55] Equation (s19)
Figure JPOXMLDOC01-appb-C000098
[Wherein, m2 represents an integer of 0 to 6, A14 and A15 each independently represent a halogen atom, a cyano group, or a C1 to C6 alkyl group, and A16 represents a hydrogen atom, a halogen atom. Or A1 represents a C1 to C6 alkoxy group, A17 represents a halogen atom or a C1 to C6 alkoxy group, and when m2 is 2 or more, two or more A17 each represent an independent substituent, and May be different. (See WO 05/121104),
［ｂ－２３．５６］式（ｓ２０）
Figure JPOXMLDOC01-appb-C000099
［式中、Ａ１８およびＡ１９は、それぞれ独立していて、ハロゲン原子、シアノ基、またはＣ１～Ｃ６のアルキル基を表し、Ａ２０、Ａ２１およびＡ２２は、それぞれ独立していて、水素原子、ハロゲン原子、またはＣ１～Ｃ６のアルコキシ基を表す。］で表される化合物（国際公開第０７／０６６６０１号参照）、 [B-23.56] Equation (s20)
Figure JPOXMLDOC01-appb-C000099
[In the formula, A18 and A19 each independently represent a halogen atom, a cyano group, or a C1-C6 alkyl group; A20, A21 and A22 each independently represent a hydrogen atom, a halogen atom, Or a C1-C6 alkoxy group. (See WO07 / 066601),
［ｂ－２３．５７］式（ｓ２１）
Figure JPOXMLDOC01-appb-C000100
［式中、Ａ２３およびＡ２４は、それぞれ独立していて、水素原子、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表し、Ｘは、酸素原子または硫黄原子を表す。］で表される化合物（国際公開第０７／０８７９０６号、国際特許第０９／０１６２２０号、国際特許第１０／１３０７６７号参照）、 [B-23.57] Equation (s21)
Figure JPOXMLDOC01-appb-C000100
[In the formula, A23 and A24 are each independently a hydrogen atom, a halogen atom, a C1-C6 alkyl group or a C3-C8 cycloalkyl group, and X represents an oxygen atom or a sulfur atom. (See WO 07/087906, WO 09/016220, WO 10/130767),
［ｂ－２３．５８］式（ｓ２２）
Figure JPOXMLDOC01-appb-C000101
［式中、ｍ３は、０～５の整数を表し、Ａ２５は、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、またはＣ３～Ｃ８のシクロアルキル基を表し、ｍ３が２以上の場合、２以上のＡ２５は、それぞれ独立した置換基を表し、同一または異なっていてよい。］で表される化合物（国際公開第１３／０９２２２４号参照）、 [B-23.58] Equation (s22)
Figure JPOXMLDOC01-appb-C000101
[In the formula, m3 represents an integer of 0 to 5, A25 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, Alternatively, when C3 to C8 are a cycloalkyl group, and m3 is 2 or more, two or more A25s each represent an independent substituent, which may be the same or different. (See WO 13/092224),
［ｂ－２３．５９］式（ｓ２３）
Figure JPOXMLDOC01-appb-C000102
［式中、Ａ２６は、水素原子、またはハロゲン原子を表し、Ｖ１およびＶ２は、それぞれ独立していて、酸素原子、または硫黄原子を表す。］で表される化合物（国際公開第１２／０２５４５０号参照）、 [B-23.59] Equation (s23)
Figure JPOXMLDOC01-appb-C000102
[In the formula, A26 represents a hydrogen atom or a halogen atom, and V1 and V2 each independently represent an oxygen atom or a sulfur atom. ] (See WO 12/025450),
［ｂ－２３．６０］式（ｓ２４）または式（ｓ２５）
Figure JPOXMLDOC01-appb-C000103
［式中、ｍ４は、０～５の整数を表し、Ａ２７は、Ｃ１～Ｃ６のアルキル基を表し、Ａ２８は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、ｍ４が２以上の場合、２以上のＡ２８は、それぞれ独立した置換基を表し、同一または異なっていてよく、Ａ２９は、Ｃ１～Ｃ６のアルキル基、Ｃ２～Ｃ６のアルケニル基、またはＣ３～Ｃ６のアルキニル基を表す。］で表される化合物（国際公開第１３／０３７７１７号参照）、 [B-23.60] Equation (s24) or Equation (s25)
Figure JPOXMLDOC01-appb-C000103
[In the formula, m4 represents an integer of 0 to 5, A27 represents a C1 to C6 alkyl group, and A28 represents a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group. And when m4 is 2 or more, two or more A28s each represent an independent substituent and may be the same or different, and A29 is a C1-C6 alkyl group, a C2-C6 alkenyl group, or a C3 Represents an alkynyl group of -C6. ] (See WO 13/037771),
［ｂ－２３．６１］式（ｓ２６）または式（ｓ２７）
Figure JPOXMLDOC01-appb-C000104
［式中、ｍ５は、０～５の整数を表し、Ａ３０は、Ｃ１～Ｃ６のアルキル基を表し、Ａ３１は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、ｍ５が２以上の場合、２以上のＡ３１は、それぞれ独立した置換基を表し、同一または異なっていてよく、Ａ３２は、Ｃ１～Ｃ６のアルキル基、Ｃ２～Ｃ６のアルケニル基、またはＣ３～Ｃ６のアルキニル基を表す。］で表される化合物（国際公開第１３／０３７７１７号参照）、 [B-23.61] Equation (s26) or Equation (s27)
Figure JPOXMLDOC01-appb-C000104
[Wherein, m5 represents an integer of 0 to 5, A30 represents a C1 to C6 alkyl group, A31 represents a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group. And when m5 is 2 or more, two or more A31s each represent an independent substituent and may be the same or different, and A32 is a C1-C6 alkyl group, a C2-C6 alkenyl group, or a C3 Represents an alkynyl group of -C6. ] (See WO 13/037771),
［ｂ－２３．６２］式（ｓ２８）
Figure JPOXMLDOC01-appb-C000105
［式中、Ａ３３、Ａ３４、Ａ３５およびＡ３６は、それぞれ独立していて、水素原子、またはハロゲン原子を表し、Ａ３７は、水素原子、アセチル基、またはベンゾイル基を表す。］で表される化合物（国際公開第０６／０３１６３１号、国際特許第１０／０６９８８２号参照）、 [B-23.62] Equation (s28)
Figure JPOXMLDOC01-appb-C000105
[Wherein, A33, A34, A35 and A36 each independently represent a hydrogen atom or a halogen atom, and A37 represents a hydrogen atom, an acetyl group or a benzoyl group. (See WO 06/031631, WO 10/069882),
［ｂ－２３．６３］式（ｓ２９）
Figure JPOXMLDOC01-appb-C000106
［式中、Ａ３８は、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、Ａ３９およびＡ４０は、それぞれ独立していて、水素原子、またはハロゲン原子を表す。］で表される化合物（国際公開第１４／０４３３７６号参照）、 [B-23.63] Equation (s29)
Figure JPOXMLDOC01-appb-C000106
[In the formula, A38 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and A39 and A40 each independently represent a hydrogen atom or a halogen atom. ] (See WO 14/043376),
［ｂ－２３．６４］式（ｓ３０）
Figure JPOXMLDOC01-appb-C000107
［式中、Ａ４１は、水素原子、水硫基（－ＳＨ）、チオシアン酸基（－ＳＣＮ）、またはＣ１～Ｃ６のアルキルチオ基を表し、Ａ４２、Ａ４３、Ａ４４およびＡ４５は、それぞれ独立していて、水素原子、またはハロゲン原子を表す。］で表される化合物（国際公開第０９／０７７４４３号参照）、 [B-23.64] Formula (s30)
Figure JPOXMLDOC01-appb-C000107
[In the formula, A41 represents a hydrogen atom, a hydroxyl group (—SH), a thiocyanate group (—SCN), or an alkylthio group of C1 to C6, and A42, A43, A44, and A45 are each independently , A hydrogen atom, or a halogen atom. (See WO 09/077443),
［ｂ－２３．６５］式（ｓ３１）または式（ｓ３２）
Figure JPOXMLDOC01-appb-C000108
［式中、Ａ４６は、水素原子、またはハロゲン原子を表し、Ａ４７は、Ｃ１～Ｃ６のアルキル基を表し、Ａ４８は、ハロゲン原子を表す。］で表される化合物（国際公開第１１／０７０７７１号参照）、 [B-23.65] Formula (s31) or Formula (s32)
Figure JPOXMLDOC01-appb-C000108
[In the formula, A46 represents a hydrogen atom or a halogen atom, A47 represents a C1-C6 alkyl group, and A48 represents a halogen atom. (See WO 11/070771),
［ｂ－２３．６６］式（ｓ３３）
Figure JPOXMLDOC01-appb-C000109
［式中、Ａ４９、Ａ５０およびＡ５１は、それぞれ独立していて、水素原子、またはハロゲン原子を表す。］で表される化合物（国際公開第１１／０８１１７４号参照）等が挙げられる。 [B-23.66] Formula (s33)
Figure JPOXMLDOC01-appb-C000109
[Wherein, A49, A50 and A51 each independently represent a hydrogen atom or a halogen atom. And the like (see International Publication No. 11/081174).
　本発明化合物と混合して使用することができる殺虫剤に含まれる具体的な成分は、以下の群ｃで例示され、これらの塩、異性体およびＮ－オキシド体を含む。ただし、公知の殺虫剤はこれらに限定されるものではない。 具体 Specific components contained in the insecticide which can be used by mixing with the compound of the present invention are exemplified by the following group c, and include salts, isomers and N-oxides thereof. However, known insecticides are not limited to these.
群ｃ：
ｃ－１：カーバメート系アセチルコリンエステラーゼ（ＡＣｈＥ）阻害剤
　カーバメート系アセチルコリンエステラーゼ（ＡＣｈＥ）阻害剤として、［ｃ－１．１］ホスホカルブ（ｐｈｏｓｐｈｏｃａｒｂ）、［ｃ－１．２］アラニカルブ（ａｌａｎｙｃａｒｂ）、［ｃ－１．３］ブトカルボキシム（ｂｕｔｏｃａｒｂｏｘｉｍ）、［ｃ－１．４］ブトキシカルボキシム（ｂｕｔｏｘｙｃａｒｂｏｘｉｍ）、［ｃ－１．５］チオジカルブ（ｔｈｉｏｄｉｃａｒｂ）、［ｃ－１．６］チオファノックス（ｔｈｉｏｆａｎｏｘ）、［ｃ－１．７］アルジカルブ（ａｌｄｉｃａｒｂ）、［ｃ－１．８］ベンジオカルブ（ｂｅｎｄｉｏｃａｒｂ）、［ｃ－１．９］ベンフラカルブ（ｂｅｎｆｕｒａｃａｒｂ）、［ｃ－１．１０］カルバリル（ｃａｒｂａｒｙｌ）、［ｃ－１．１１］カルボフラン（ｃａｒｂｏｆｕｒａｎ）、［ｃ－１．１２］カルボスルファン（ｃａｒｂｏｓｕｌｆａｎ）、［ｃ－１．１３］エチオフェンカルブ（ｅｔｈｉｏｆｅｎｃａｒｂ）、［ｃ－１．１４］フェノブカルブ（ｆｅｎｏｂｕｃａｒｂ）、［ｃ－１．１５］ホルメタネート（ｆｏｒｍｅｔａｎａｔｅ）、［ｃ－１．１６］フラチオカルブ（ｆｕｒａｔｈｉｏｃａｒｂ）、［ｃ－１．１７］イソプロカルブ（ｉｓｏｐｒｏｃａｒｂ）、［ｃ－１．１８］メチオカルブ（ｍｅｔｈｉｏｃａｒｂ）、［ｃ－１．１９］メソミル（ｍｅｔｈｏｍｙｌ）、［ｃ－１．２０］オキサミル（ｏｘａｍｙｌ）、［ｃ－１．２１］ピリミカルブ（ｐｉｒｉｍｉｃａｒｂ）、［ｃ－１．２２］プロポキスル（ｐｒｏｐｏｘｕｒ）、［ｃ－１．２３］トリメタカルブ（ｔｒｉｍｅｔｈａｃａｒｂ）、［ｃ－１．２４］ＸＭＣ（３，５－ｘｙｌｙｌ　ｍｅｔｈｙｌｃａｒｂａｍａｔｅ）、［ｃ－１．２５］アリキシカルブ（ａｌｌｙｘｙｃａｒｂ）、［ｃ－１．２６］アルドキシカルブ（ａｌｄｏｘｙｃａｒｂ）、［ｃ－１．２７］ブフェンカルブ（ｂｕｆｅｎｃａｒｂ）、［ｃ－１．２８］ブタカルブ（ｂｕｔａｃａｒｂ）、［ｃ－１．２９］カーバノレート（ｃａｒｂａｎｏｌａｔｅ）、［ｃ－１．３０］メトルカルブ（ｍｅｔｏｌｃａｒｂ）、［ｃ－１．３１］キシルイルカルブ（ｘｙｌｙｌｃａｒｂ）、［ｃ－１．３２］フェノチオカルブ（ｆｅｎｏｔｈｉｏｃａｒｂ）、［ｃ－１．３３］キシリルカルブ（ｘｙｌｙｌｃａｒｂ）、［ｃ－１．３４］ベンダイオカルブ（ｂｅｎｄｉｏｃａｒｂ）等が挙げられる。 Group c:
c-1: Carbamate acetylcholinesterase (AChE) inhibitor As a carbamate acetylcholinesterase (AChE) inhibitor, [c-1.1] phosphocarb, [c-1.2] alanicarb, [c] -1.3] butoxycarboxym, [c-1.4] butoxycarboxim, [c-1.5] thiodicarb, [c-1.6] thiofanox ), [C-1.7] aldicarb, [c-1.8] bendiocarb, [c-1.9] benfuracarb, [c-1.10] carbaryl ryl), [c-1.11] carbofuran, [c-1.12] carbosulfan, [c-1.13] ethiofencarb, [c-1.14] fenobcarb ( fenobucarb, [c-1.15] formetanate, [c-1.16] furathiocarb, [c-1.17] isoprocarb, [c-1.18] methiocarb , [C-1.19] methomyl, [c-1.20] oxamyl, [c-1.21] pirimicarb, [c-1.22] propoxur, c-1.23] trimetacarb, [c-1.24] XMC (3,5-xylylmethylcarbamate), [c-1.25] alixycarb, [c-1.25] aldoxycarb (Aldoxycarb), [c-1.27] bufencarb, [c-1.28] butacarb, [c-1.29] carbanolate, [c-1.30] metolcarb ), [C-1.31] xylylcarb, [c-1.32] phenothiocarb, [c-1.33] xylylcarb, [c-1.34] bendiocarb bendiocarb), and the like.
ｃ－２：有機リン系アセチルコリンエステラーゼ（ＡＣｈＥ）阻害剤
　有機リン系アセチルコリンエステラーゼ（ＡＣｈＥ）阻害剤として、［ｃ－２．１］アセフェート（ａｃｅｐｈａｔｅ）、［ｃ－２．２］アザメチホス（ａｚａｍｅｔｈｉｐｈｏｓ）、［ｃ－２．３］アジンホス－メチル（ａｚｉｎｐｈｏｓ－ｍｅｔｈｙｌ）、［ｃ－２．４］アジンホス－エチル（ａｚｉｎｐｈｏｓ－ｅｔｈｙｌ）、［ｃ－２．５］エセフォン（ｅｔｈｅｐｈｏｎ）、［ｃ－２．６］カズサホス（ｃａｄｕｓａｆｏｓ）、［ｃ－２．７］クロルエトキシホス（ｃｈｌｏｒｅｔｈｏｘｙｆｏｓ）、［ｃ－２．８］クロルフェンビンホス（ｃｈｌｏｒｆｅｎｖｉｎｐｈｏｓ）、［ｃ－２．９］クロルメホス（ｃｈｌｏｒｍｅｐｈｏｓ）、［ｃ－２．１０］クロルピリホス（ｃｈｌｏｒｐｙｒｉｆｏｓ）、［ｃ－２．１１］クロルピリホス－メチル（ｃｈｌｏｒｐｙｒｉｆｏｓ－ｍｅｔｈｙｌ）、［ｃ－２．１２］クマホス（ｃｏｕｍａｐｈｏｓ）、［ｃ－２．１３］シアノホス（ｃｙａｎｏｐｈｏｓ）、［ｃ－２．１４］デメトン－Ｓ－メチル（ｄｅｍｅｔｏｎ－Ｓ－ｍｅｔｈｙｌ）、［ｃ－２．１５］ダイアジノン（ｄｉａｚｉｎｏｎ）、［ｃ－２．１６］ジクロフェンチオン（ｄｉｃｈｌｏｆｅｎｔｈｉｏｎ）、［ｃ－２．１７］ジクロルボス（ｄｉｃｈｌｏｒｖｏｓ）、［ｃ－２．１８］ジクロトホス（ｄｉｃｒｏｔｏｐｈｏｓ）、［ｃ－２．１９］ジメトエート（ｄｉｍｅｔｈｏａｔｅ）、［ｃ－２．２０］ジメチルビンホス（ｄｉｍｅｔｈｙｌｖｉｎｐｈｏｓ）、［ｃ－２．２１］ジスルホトン（ｄｉｓｕｌｆｏｔｏｎ）、［ｃ－２．２２］Ｏ－エチル　Ｏ－４－ニトロフェニル　フェニルホスホノチオアート（Ｏ－ｅｔｈｙｌ　Ｏ－４－ｎｉｔｒｏｐｈｅｎｙｌ　ｐｈｅｎｙｌｐｈｏｓｐｈｏｎｏｔｈｉｏａｔｅ）、［ｃ－２．２３］エチオン（ｅｔｈｉｏｎ）、［ｃ－２．２４］エトプロホス（ｅｔｈｏｐｒｏｐｈｏｓ）、［ｃ－２．２５］ファムフール（ｆａｍｐｈｕｒ）、［ｃ－２．２６］フェナミホス（ｆｅｎａｍｉｐｈｏｓ）、［ｃ－２．２７］フェニトロチオン（ｆｅｎｉｔｒｏｔｈｉｏｎ）、［ｃ－２．２８］フェンチオン（ｆｅｎｔｈｉｏｎ）、［ｃ－２．２９］ホスチアゼート（ｆｏｓｔｈｉａｚａｔｅ）、［ｃ－２．３０］ヘプテノホス（ｈｅｐｔｅｎｏｐｈｏｓ）、［ｃ－２．３１］イソフェンホス－メチル（ｉｓｏｆｅｎｐｈｏｓ－ｍｅｔｈｙｌ）、［ｃ－２．３２］イソカルボホス（Ｉｓｏｃａｒｂｏｐｈｏｓ）、［ｃ－２．３３］イソキサチオン（ｉｓｏｘａｔｈｉｏｎ）、［ｃ－２．３４］マラチオン（ｍａｌａｔｈｉｏｎ）、［ｃ－２．３５］メカルバム（ｍｅｃａｒｂａｍ）、［ｃ－２．３６］メタミドホス（ｍｅｔｈａｍｉｄｏｐｈｏｓ）、［ｃ－２．３７］メチダチオン（ｍｅｔｈｉｄａｔｈｉｏｎ）、［ｃ－２．３８］メビンホス（ｍｅｖｉｎｐｈｏｓ）、［ｃ－２．３９］モノクロトホス（ｍｏｎｏｃｒｏｔｏｐｈｏｓ）、［ｃ－２．４０］ナレッド（ｎａｌｅｄ）、［ｃ－２．４１］オメトエート（ｏｍｅｔｈｏａｔｅ）、［ｃ－２．４２］オキシデメトン－メチル（ｏｘｙｄｅｍｅｔｏｎ－ｍｅｔｈｙｌ）、［ｃ－２．４３］パラチオン（ｐａｒａｔｈｉｏｎｓ）、［ｃ－２．４４］パラチオン－メチル（ｐａｒａｔｈｉｏｎ－ｍｅｔｈｙｌ）、［ｃ－２．４５］フェントエート（ｐｈｅｎｔｈｏａｔｅ）、［ｃ－２．４６］ホレート（ｐｈｏｒａｔｅ）、［ｃ－２．４７］ホサロン（ｐｈｏｓａｌｏｎｅ）、［ｃ－２．４８］ホスメット（ｐｈｏｓｍｅｔ）、［ｃ－２．４９］ホスファミドン（ｐｈｏｓｐｈａｍｉｄｏｎ）、［ｃ－２．５０］ホキシム（ｐｈｏｘｉｍ）、［ｃ－２．５１］ピリミホス－メチル（ｐｉｒｉｍｉｐｈｏｓ－ｍｅｔｈｙｌ）、［ｃ－２．５２］プロフェノホス（ｐｒｏｆｅｎｏｆｏｓ）、［ｃ－２．５３］プロペタンホス（ｐｒｏｐｅｔａｍｐｈｏｓ）、［ｃ－２．５４］プロチオホス（ｐｒｏｔｈｉｏｆｏｓ）、［ｃ－２．５５］ピラクロホス（ｐｙｒａｃｌｏｆｏｓ）、［ｃ－２．５６］ピリダフェンチオン（ｐｙｒｉｄａｐｈｅｎｔｈｉｏｎ）、［ｃ－２．５７］キナルホス（ｑｕｉｎａｌｐｈｏｓ）、［ｃ－２．５８］スルホテップ（ｓｕｌｆｏｔｅｐ）、［ｃ－２．５９］テブピリムホス（ｔｅｂｕｐｉｒｉｍｆｏｓ）、［ｃ－２．６０］テメホス（ｔｅｍｅｐｈｏｓ）、［ｃ－２．６１］テルブホス（ｔｅｒｂｕｆｏｓ）、［ｃ－２．６２］チオメトン（ｔｈｉｏｍｅｔｏｎ）、［ｃ－２．６３］トリアゾホス（ｔｒｉａｚｏｐｈｏｓ）、［ｃ－２．６４］トリクロルホン（ｔｒｉｃｈｌｏｒｆｏｎ）、［ｃ－２．６５］バミドチオン（ｖａｍｉｄｏｔｈｉｏｎ）、［ｃ－２．６６］クロルチオン（ｃｈｌｏｒｏｔｈｉｏｎ）、［ｃ－２．６７］ブロムフェンビンホス（ｂｒｏｍｆｅｎｖｉｎｆｏｓ）、［ｃ－２．６８］ブロモホス（ｂｒｏｍｏｐｈｏｓ）、［ｃ－２．６９］ブロモホス－エチル（ｂｒｏｍｏｐｈｏｓ－ｅｔｈｙｌ）、［ｃ－２．７０］ブタチオホス（ｂｕｔａｔｈｉｏｆｏｓ）、［ｃ－２．７１］カルボフェノチオン（ｃａｒｂｏｐｈｅｎｏｔｈｉｏｎ）、［ｃ－２．７２］クロルホキシム（ｃｈｌｏｒｐｈｏｘｉｍ）、［ｃ－２．７３］スルプロホス（ｓｕｌｐｒｏｆｏｓ）、［ｃ－２．７４］ジアミダホス（ｄｉａｍｉｄａｆｏｓ）、［ｃ－２．７５］テトラクロルビンホス（ｔｅｔｒａｃｈｌｏｒｖｉｎｐｈｏｓ）、［ｃ－２．７６］プロパホス（ｐｒｏｐａｐｈｏｓ）、［ｃ－２．７７］メスルフェンホス（ｍｅｓｕｌｆｅｎｆｏｓ）、［ｃ－２．７８］ジオキサベンゾホス（ｄｉｏｘａｂｅｎｚｏｆｏｓ）、［ｃ－２．７９］エトリムホス（ｅｔｒｉｍｆｏｓ）、［ｃ－２．８０］オキシデプロホス（ｏｘｙｄｅｐｒｏｆｏｓ）、［ｃ－２．８１］ホルモチオン（ｆｏｒｍｏｔｈｉｏｎ）、［ｃ－２．８２］フェンスルホチオン（ｆｅｎｓｕｌｆｏｔｈｉｏｎ）、［ｃ－２．８３］イサゾホス（ｉｓａｚｏｆｏｓ）、［ｃ－２．８４］イミシアホス（ｉｍｉｃｙａｆｏｓ）、［ｃ－２．８５］イサミドホス（ｉｓａｍｉｄｏｆｏｓ）、［ｃ－２．８６］チオナジン（ｔｈｉｏｎａｚｉｎ）、［ｃ－２．８７］ホスチエタン（ｆｏｓｔｈｉｅｔａｎ）等が挙げられる。 c-2: Organophosphorus acetylcholinesterase (AChE) inhibitor As the organophosphorus acetylcholinesterase (AChE) inhibitor, [c-2.1] acephate, [c-2.2] azamethiphos, [C-2.3] Azinphos-methyl, [c-2.4] Azinphos-ethyl, [c-2.5] Ethephon, [c-2.6] ] Cadusafos, [c-2.7] chlorethoxyphos, [c-2.8] chlorfenvinphos, [c-2.9] chlormephos, [c- 2.10] black Lupyrifos (chlorpyrifos), [c-2.11] Chlorpyrifos-methyl, [c-2.12] Coumaphos, [c-2.13] Cyanophos, [c-2. 14] demeton-S-methyl, [c-2.15] diazinon, [c-2.16] dichlofenthion, [c-2.17] dichlorvos , [C-2.18] dicrotophos, [c-2.19] dimethoate, [c-2.20] dimethylvinphos, [c-2.21] disul Disulfonton, [c-2.22] O-ethyl O-4-nitrophenyl phenylphosphonothioate (O-ethyl O-4-nitrophenyl phenylphosphonothioate), [c-2.23] ethion, [ c-2.24] etoprophos, [c-2.25] famfur, [c-2.26] fenamiphos, [c-2.27] fenitrothion, [c- 2.28] fenthion, [c-2.29] phosthiazate, [c-2.30] heptenophos, [c-2.31] isofenphos-methyl isofenphos-methyl, [c-2.32] isocarbobophos, [c-2.33] isoxathion, [c-2.34] malathion, [c-2.35] mecarbam ( mecarbam), [c-2.36] methamidophos, [c-2.37] methidathion, [c-2.38] mevinphos, [c-2.39] monocrotophos ), [C-2.40] nared, [c-2.41] omethoate, [c-2.42] oxydemethon-methyl, [c-2.4] ] Parathions, [c-2.44] parathion-methyl, [c-2.45] phenthoate, [c-2.46] phorate, [c-2] .47] phosphorone, [c-2.48] phosmet, [c-2.49] phosphamidon, [c-2.50] phoxim, [c-2.51] ] Pirimiphos-methyl, [c-2.52] propenofos, [c-2.53] propetamphos, [c-2.54] prothiophos, [c-2] .55] Pyraclofos, [c-2.56] pyridaphenthion, [c-2.57] quinalphos, [c-2.58] sulfotep, [c-2.59] tebupyrimphos ( tebupirimfos), [c-2.60] temephos, [c-2.61] terbufos, [c-2.62] thiometon, [c-2.63] triazophos , [C-2.64] trichlorfon, [c-2.65] vamidithion, [c-2.66] chlorthion, [c-2.67] bromophene Bromfenvinfos, [c-2.68] bromophos, [c-2.69] bromophos-ethyl, [c-2.70] butathiophos, [c-2. 71] carbophenothion, [c-2.72] chlorphoxim, [c-2.73] sulprofos, [c-2.74] diamidafos, [c-2. 75] tetrachlorvinphos, [c-2.76] propaphos, [c-2.77] mesulfenphos, [c-2.78] dioxabenzo (Dioxabenzofos), [c-2.79] etrimfos, [c-2.80] oxydeprofos, [c-2.81] formothion, [c-2.82] Fensulfothion, [c-2.83] isazofos, [c-2.84] imiciafos, [c-2.85] isamidofos, [c-2.86] thionazine ( thionazin), [c-2.87] fosthiethane, and the like.
ｃ－３：ＧＡＢＡ作動性塩素イオンチャネルブロッカー
　ＧＡＢＡ作動性塩素イオンチャネルブロッカーとして、［ｃ－３．１］クロルデン（ｃｈｌｏｒｄａｎｅ）、［ｃ－３．２］エンドスルファン（ｅｎｄｏｓｕｌｆａｎ）、［ｃ－３．３］リンデン（ｌｉｎｄａｎｅ）、［ｃ－３．４］ジエノクロル（ｄｉｅｎｏｃｈｌｏｒ）、［ｃ－３．５］エチプロール（ｅｔｈｉｐｒｏｌｅ）、［ｃ－３．６］フィプロニル（ｆｉｐｒｏｎｉｌ）、［ｃ－３．７］アセトプロール（ａｃｅｔｏｐｒｏｌｅ）等が挙げられる。 c-3: GABA-operated chloride channel blocker [c-3.1] chlordane, [c-3.2] endosulfan, [c-3.3] as GABA-operated chloride channel blockers. ] Lindane, [c-3.4] dienochlor, [c-3.5] ethiprole, [c-3.6] fipronil, [c-3.7] aceto Aceproprole and the like.
ｃ－４：ナトリウムチャネルモジュレーター
　ナトリウムチャネルモジュレーターとして、［ｃ－４．１］アクリナトリン（ａｃｒｉｎａｔｈｒｉｎ）、［ｃ－４．２］アレスリン［（１Ｒ）－アイソマー］（ａｌｌｅｔｈｒｉｎ［（１Ｒ）－ｉｓｏｍｅｒ］）、［ｃ－４．３］ビフェントリン（ｂｉｆｅｎｔｈｒｉｎ）、［ｃ－４．４］ビオアレスリン（ｂｉｏａｌｌｅｔｈｒｉｎ）、［ｃ－４．５］ビオアレスリン　Ｓ－シクロペンテニル　アイソマー（ｂｉｏａｌｌｅｔｈｒｉｎ　Ｓ－ｃｙｃｌｏｐｅｎｔｅｎｙｌ　　ｉｓｏｍｅｒ）、［ｃ－４．６］ビオレスメトリン（ｂｉｏｒｅｓｍｅｔｈｒｉｎ）、［ｃ－４．７］シクロプロトリン（ｃｙｃｌｏｐｒｏｔｈｒｉｎ）、［ｃ－４．８］シフルトリン（ｃｙｆｌｕｔｈｒｉｎ）、［ｃ－４．９］ベータ－シフルトリン（ｂｅｔａ－ｃｙｆｌｕｔｈｒｉｎ）、［ｃ－４．１０］シハロトリン（ｃｙｈａｌｏｔｈｒｉｎ）、［ｃ－４．１１］ガンマ－シハロトリン（ｇａｍｍａ－ｃｙｈａｌｏｔｈｒｉｎ）、［ｃ－４．１２］ラムダ－シハロトリン（ｌａｍｂｄａ－ｃｙｈａｌｏｔｈｒｉｎ）、［ｃ－４．１３］シペルメトリン（ｃｙｐｅｒｍｅｔｈｒｉｎ）、［ｃ－４．１４］アルファ－シペルメトリン（ａｌｐｈａ－ｃｙｐｅｒｍｅｔｈｒｉｎ）、［ｃ－４．１５］ベータ－シペルメトリン（ｂｅｔａ－ｃｙｐｅｒｍｅｔｈｒｉｎ）、［ｃ－４．１６］セタ－シペルメトリン（ｔｈｅｔａ－ｃｙｐｅｒｍｅｔｈｒｉｎ）、［ｃ－４．１７］ゼダ－シペルメトリン（ｚｅｔａ－ｃｙｐｅｒｍｅｔｈｒｉｎ）、［ｃ－４．１８］シフェノトリン［（１Ｒ）－トランス－アイソマー］（ｃｙｐｈｅｎｏｔｈｒｉｎ［（１Ｒ）－ｔｒａｎｓ－ｉｓｏｍｅｒ］）、［ｃ－４．１９］デルタメトリン（ｄｅｌｔａｍｅｔｈｒｉｎ）、［ｃ－４．２０］エンペントリン［（ＥＺ）－（１Ｒ）－アイソマー］（ｅｍｐｅｎｔｈｒｉｎ［（ＥＺ）－（１Ｒ）－ｉｓｏｍｅｒ］）、［ｃ－４．２１］エスフェンバレレート（ｅｓｆｅｎｖａｌｅｒａｔｅ）、［ｃ－４．２２］エトフェンプロックス（ｅｔｈｏｆｅｎｐｒｏｘ）、［ｃ－４．２３］フェンプロパトリン（ｆｅｎｐｒｏｐａｔｈｒｉｎ）、［ｃ－４．２４］フェンバレレート（ｆｅｎｖａｌｅｒａｔｅ）、［ｃ－４．２５］フルシトリネート（ｆｌｕｃｙｔｈｒｉｎａｔｅ）、［ｃ－４．２６］フルメトリン（ｆｌｕｍｅｔｈｒｉｎ）、［ｃ－４．２７］タウ－フルバリネート（ｔａｕ－ｆｌｕｖａｌｉｎａｔｅ）、［ｃ－４．２８］ハルフェンプロックス（ｈａｌｆｅｎｐｒｏｘ）、［ｃ－４．２９］イミプロトリン（ｉｍｉｐｒｏｔｈｒｉｎ）、［ｃ－４．３０］メトトリン（ｍｅｔｈｏｔｈｒｉｎ）、［ｃ－４．３１］メトフルトリン（ｍｅｔｏｆｌｕｔｈｒｉｎ）、［ｃ－４．３２］イプシロン－メトフルトリン（ｅｐｓｉｌｏｎ－ｍｅｔｏｆｌｕｔｈｒｉｎ）、［ｃ－４．３３］モンフルオロトリン（ｍｏｍｆｌｕｏｒｏｔｈｒｉｎ）、［ｃ－４．３４］イプシロン－モンフルオロトリン（ｅｐｓｉｌｏｎ－ｍｏｍｆｌｕｏｒｏｔｈｒｉｎ）、［ｃ－４．３５］ペルメトリン（ｐｅｒｍｅｔｈｒｉｎ）、［ｃ－４．３６］フェノトリン［（１Ｒ）－トランス－アイソマー］（ｐｈｅｎｏｔｈｒｉｎ［（１Ｒ）－ｔｒａｎｓ－ｉｓｏｍｅｒ］）、［ｃ－４．３７］プラレトリン（ｐｒａｌｌｅｔｈｒｉｎ）、［ｃ－４．３８］レスメトリン（ｒｅｓｍｅｔｈｒｉｎ）、［ｃ－４．３９］カデトリン（ｋａｄｅｔｈｒｉｎ）、［ｃ－４．４０］シラフルオフェン（ｓｉｌａｆｌｕｏｆｅｎ）、［ｃ－４．４１］テフルトリン（ｔｅｆｌｕｔｈｒｉｎ）、［ｃ－４．４２］テトラメトリン（ｔｅｔｒａｍｅｔｈｒｉｎ）、［ｃ－４．４３］テトラメトリン［（１Ｒ）－アイソマー］（ｔｅｔｒａｍｅｔｈｒｉｎ［（１Ｒ）－ｉｓｏｍｅｒ］）、［ｃ－４．４４］トラロメトリン（ｔｒａｌｏｍｅｔｈｒｉｎ）、［ｃ－４．４５］トランスフルトリン（ｔｒａｎｓｆｌｕｔｈｒｉｎ）、［ｃ－４．４６］ＺＸＩ８９０１（３－（４－ｂｒｏｍｏｐｈｅｎｏｘｙ）ｐｈｅｎｙｌ］－ ｃｙａｎｏｍｅｔｈｙｌ ４－（ｄｉｆｌｕｏｒｏｍｅｔｈｏｘｙ）－α－ （１－ｍｅｔｈｙｌｅｔｈｙｌ）ｂｅｎｚｅｎｅａｃｅｔａｔｅ）、［ｃ－４．４７］バイオペルメトリン（ｂｉｏｐｅｒｍｅｔｈｒｉｎ）、［ｃ－４．４８］フラメトリン（ｆｕｒａｍｅｔｈｒｉｎ）、［ｃ－４．４９］プロフルトリン（ｐｒｏｆｌｕｔｈｒｉｎ）、［ｃ－４．５０］フルブロシトリネート（ｆｌｕｂｒｏｃｙｔｈｒｉｎａｔｅ）、［ｃ－４．５１］ジメフルトリン（ｄｉｍｅｆｌｕｔｈｒｉｎ）、［ｃ－４．５２］ＤＤＴ（ｄｉｃｈｌｏｒｏ－ｄｉｐｈｅｎｙｌ－ｔｒｉｃｈｌｏｒｏｅｔｈａｎｅ）、［ｃ－４．５３］メトキシクロル（ｍｅｔｈｏｘｙｃｈｌｏｒ）、［ｃ－４．５４］フェノトリン（ｐｈｅｎｏｔｈｒｉｎ）、［ｃ－４．５５］フルバリネート（ｆｌｕｖａｌｉｎａｔｅ）等が挙げられる。 c-4: Sodium channel modulator As a sodium channel modulator, [c-4.1] acrinathrin, [c-4.2] arethrin [(1R) -isomer] (allethrin [(1R) -isomer]), [C-4.3] bifenthrin, [c-4.4] bioallethrin, [c-4.5] bioallethrin S-cyclopentenyl isomer (bioallthrin S-cyclopentenyl isomer), [-c- 4.6] bioresmethrin, [c-4.7] cycloprothrin, [c-4.8] cyfluthrin, [c-4. Beta-cyfluthrin, [c-4.10] cyhalothrin, [c-4.11] gamma-cyhalothrin, [c-4.12] lambda-cyhalothrin (lambda) -Cyhalothrin, [c-4.13] cypermethrin, [c-4.14] alpha-cypermethrin, [c-4.15] beta-cypermethrin , [C-4.16] theta-cypermethrin, [c-4.17] zeda-cypermethrin, [c-4.18] cyphe Trin [(1R) -trans-isomer] (cyphenothrin [(1R) -trans-isomer]), [c-4.19] deltamethrin, [c-4.20] empentrin [(EZ)-(1R) ) -Isomer] (empenthrin [(EZ)-(1R) -isomer]), [c-4.21] esfenvalerate, [c-4.22] ethofenprox, [c- 4.23] fenpropathrin, [c-4.24] fenvalerate, [c-4.25] flucytrinate, [c-4.26] flumethrin ), [C-4.27] tau-fluvalinate, [c-4.28] halfenprox, [c-4.29] imiprothrin, [c-4. 30] methotrin, [c-4.31] methfluthrin, [c-4.32] epsilon-methfluthrin, [c-4.33] monfluorothrin, [c-4.33] methfluorothrin c-4.34] epsilon-momofluorothrin, [c-4.35] permethrin, [c-4.36] phenothrin [(1R) -trans-A Sommer] (phenothrin [(1R) -trans-isomer]), [c-4.37] praletrin, [c-4.38] resmethrin, [c-4.39] cadetrin , [C-4.40] silafluofen, [c-4.41] tefluthrin, [c-4.42] tetramethrin, [c-4.43] tetramethrin [(1R)- Isomer] (tetramethrin [(1R) -isomer]), [c-4.44] tralomethrin, [c-4.45] transfluthrin, [c-4.46] ZXI 901 (3- (4-bromophenoxy) phenyl] -cyanomethyl 4- (difluoromethoxy) -α- (1-methylethylene) benzenecetate, [c-4.47] biopermethrin (biopermethrin. (Furamethrin), [c-4.49] profluthrin, [c-4.50] flubrocytrinate, [c-4.51] dimfluthrin, [c-4.52] DDT (dichloro-diphenyl-trichloroethane), [c-4.53] methoxychlor, [c-4] 54] phenothrin (phenothrin), and the like [c-4.55] fluvalinate (fluvalinate).
ｃ－５：ニコチン性アセチルコリン受容体（ｎＡＣｈＲ）競合的モジュレーター
　ニコチン性アセチルコリン受容体（ｎＡＣｈＲ）競合的モジュレーターとして、［ｃ－５．１］アセタミプリド（ａｃｅｔａｍｉｐｒｉｄ）、［ｃ－５．２］クロチアニジン（ｃｌｏｔｈｉａｎｉｄｉｎ）、［ｃ－５．３］ジノテフラン（ｄｉｎｏｔｅｆｕｒａｎ）、［ｃ－５．４］イミダクロプリド（ｉｍｉｄａｃｌｏｐｒｉｄ）、［ｃ－５．５］ニテンピラム（ｎｉｔｅｎｐｙｒａｍ）、［ｃ－５．６］チアクロプリド（ｔｈｉａｃｌｏｐｒｉｄ）、［ｃ－５．７］チアメトキサム（ｔｈｉａｍｅｔｈｏｘａｍ）、［ｃ－５．８］ニコチン（ｎｉｃｏｔｉｎｅ）、［ｃ－５．９］硫酸ニコチン（ｎｉｃｏｔｉｎｅ　ｓｕｌｆａｔｅ）、［ｃ－５．１０］スルホキサフロル（ｓｕｌｆｏｘａｆｌｏｒ）、［ｃ－５．１１］フルピラジフロン（ｆｌｕｐｙｒａｄｉｆｕｒｏｎｅ）、［ｃ－５．１２］トリフルメゾピリム（ｔｒｉｆｌｕｍｅｚｏｐｙｒｉｍ）等が挙げられる。 c-5: Nicotinic Acetylcholine Receptor (nAChR) Competitive Modulator As a nicotinic acetylcholine receptor (nAChR) competitive modulator, [c-5.1] acetamipride (acetamiprid), [c-5.2] clothianidin (clothianidin) ), [C-5.3] dinotefuran, [c-5.4] imidacloprid, [c-5.5] nitenpyram, [c-5.6] thiacloprid, [C-5.7] thiamethoxam, [c-5.8] nicotine, [c-5.9] nicotine sulfate, [c-5.10] sulphate Kisafuroru (sulfoxaflor), [c-5.11] Furupirajifuron (flupyradifurone), and the like [c-5.12] triflupromazine meso pyridinium beam (triflumezopyrim).
ｃ－６：ニコチン性アセチルコリン受容体（ｎＡＣｈＲ）アロステリックモジュレーター
　ニコチン性アセチルコリン受容体（ｎＡＣｈＲ）アロステリックモジュレーターとして、［ｃ－６．１］スピノサド（ｓｐｉｎｏｓａｄ）、［ｃ－６．２］スピネトラム（ｓｐｉｎｅｔｏｒａｍ）等が挙げられる。 c-6: Nicotinic acetylcholine receptor (nAChR) allosteric modulator As a nicotinic acetylcholine receptor (nAChR) allosteric modulator, [c-6.1] spinosad (spinosad), [c-6.2] spinetoram, etc. Is mentioned.
ｃ－７：グルタミン酸作動性塩素イオンチャネル（ＧｌｕＣｌ） アロステリックモジュレーター
　グルタミン酸作動性塩素イオンチャネル（ＧｌｕＣｌ）アロステリックモジュレーターとして、［ｃ－７．１］アバメクチン（ａｂａｍｅｃｔｉｎ）、［ｃ－７．２］エマメクチン安息香酸塩（ｅｍａｍｅｃｔｉｎ　ｂｅｎｚｏａｔｅ）、［ｃ－７．３］レピメクチン（ｌｅｐｉｍｅｃｔｉｎ）、［ｃ－７．４］ミルベメクチン（ｍｉｌｂｅｍｅｃｔｉｎ）等が挙げられる。 c-7: Glutamergic chloride channel (GluCl) allosteric modulator As a glutamate-gated chloride ion channel (GluCl) allosteric modulator, [c-7.1] abamectin, [c-7.2] emamectin benzoate Salt (emmectin benzoate), [c-7.3] lepimectin, [c-7.4] milbemectin, and the like.
ｃ－８：幼若ホルモン類似剤
　幼若ホルモン類似剤として、［ｃ－８．１］ヒドロプレン（ｈｙｄｒｏｐｒｅｎｅ）、［ｃ－８．２］キノプレン（ｋｉｎｏｐｒｅｎｅ）、［ｃ－８．３］メトプレン（ｍｅｔｈｏｐｒｅｎｅ）、［ｃ－８．４］フェノキシカルブ（ｆｅｎｏｘｙｃａｒｂ）、［ｃ－８．５］ピリプロキシフェン（ｐｙｒｉｐｒｏｘｙｆｅｎ）等が挙げられる。 c-8: Juvenile hormone analogs As juvenile hormone analogs, [c-8.1] hydroprene, [c-8.2] quinoprene, [c-8.3] methoprene ), [C-8.4] phenoxycarb, [c-8.5] pyriproxyfen, and the like.
ｃ－９：非特異的（マルチサイト）阻害剤
　非特異的（マルチサイト）阻害剤として、［ｃ－９．１］臭化メチル（ｍｅｔｈｙｌ　ｂｒｏｍｉｄｅ）、［ｃ－９．２］クロルピクリン（ｃｈｌｏｒｏｐｉｃｒｉｎ）、［ｃ－９．３］クリオライト（ｃｒｙｏｌｉｔｅ）、［ｃ－９．４］フッ化スルフリル（ｓｕｌｆｕｒｙｌ　ｆｌｕｏｒｉｄｅ）、［ｃ－９．５］ホウ砂（ｂｏｒａｘ）、［ｃ－９．６］ホウ酸（ｂｏｒｉｃ　ａｃｉｄ）、［ｃ－９．７］オクタホウ酸ニナトリウム塩（ｄｉｓｏｄｉｕｍ　ｏｃｔａｂｏｒａｔｅ）、［ｃ－９．８］メタホウ酸ナトリウム塩（ｓｏｄｉｕｍ　ｍｅｔａｂｏｒａｔｅ）［ｃ－９．９］吐酒石（ｔａｒｔａｒ　ｅｍｅｔｉｃ）、［ｃ－９．１０］ダゾメット（ｄａｚｏｍｅｔ）、［ｃ－９．１１］メタム（ｍｅｔａｍ）、［ｃ－９．１２］カーバムナトリウム塩（ｍｅｔｈａｍ　ｓｏｄｉｕｍ）等が挙げられる。 c-9: Non-specific (multi-site) inhibitor As a non-specific (multi-site) inhibitor, [c-9.1] methyl bromide, [c-9.2] chloropicrin , [C-9.3] cryolite, [c-9.4] sulfuryl fluoride, [c-9.5] borax, [c-9.6] borane Acid (boric acid), [c-9.7] disodium octaborate, [c-9.8] sodium metaborate [c-9.9] tartar emetic), [c-9.10] dazomet, [c-9.11] metham (m etam), [c-9.12] carbam sodium salt and the like.
ｃ－１０：弦音器官ＴＲＰＶチャネルモジュレーター
　弦音器官ＴＲＰＶチャネルモジュレーターとして、［ｃ－１０．１］ピメトロジン（ｐｙｍｅｔｒｏｚｉｎｅ）、［ｃ－１０．２］ピリフルキナゾン（ｐｙｒｉｆｌｕｑｕｉｎａｚｏｎ）等が挙げられる。 c-10: String Organ TRPV Channel Modulator Examples of the string organ TRPV channel modulator include [c-10.1] pymetrozine, [c-10.2] pyrifluquinazone, and the like.
ｃ－１１：ダニ類成長阻害剤
　ダニ類成長阻害剤として、［ｃ－１１．１］クロフェンテジン（ｃｌｏｆｅｎｔｅｚｉｎｅ）、［ｃ－１１．２］ジフロビダジン（ｄｉｆｌｏｖｉｄａｚｉｎ）、［ｃ－１１．３］ヘキシチアゾクス（ｈｅｘｙｔｈｉａｚｏｘ）、［ｃ－１１．４］エトキサゾール（ｅｔｏｘａｚｏｌｅ）等が挙げられる。 c-11: Mite growth inhibitor As mite growth inhibitors, [c-11. 1] clofentezine, [c-11. 2] diflovidazin, [c-11. (Hexythiazox), [c-11.4] ethoxazole, and the like.
ｃ－１２：ミトコンドリアＡＴＰ合成酵素阻害剤
　ミトコンドリアＡＴＰ合成酵素阻害剤として、［ｃ－１２．１］ジアフェンチウロン（ｄｉａｆｅｎｔｈｉｕｒｏｎ）、［ｃ－１２．２］アゾシクロチン（ａｚｏｃｙｃｌｏｔｉｎ）、［ｃ－１２．３］シヘキサチン（ｃｙｈｅｘａｔｉｎ）、［ｃ－１２．４］フェンブタチンオキシド（ｆｅｎｂｕｔａｔｉｎ　ｏｘｉｄｅ）、「ｃ－１２．５」プロパルギット（ｐｒｏｐａｒｇｉｔｅ）、「ｃ－１２．６」テトラジホン（ｔｅｔｒａｄｉｆｏｎ）等が挙げられる。 c-12: Mitochondrial ATP synthase inhibitor As a mitochondrial ATP synthase inhibitor, [c-12. 1] diafenthiuron, [c-12. 2] azocyclotin, [c-12. 3] cyhexatin, [c-12.4] fenbutatin oxide, "c-12.5" propargite, "c-12.6" tetradifon, and the like. .
ｃ－１３：プロトン勾配を撹乱する酸化的リン酸化脱共役剤
　プロトン勾配を撹乱する酸化的リン酸化脱共役剤として、［ｃ－１３．１］クロルフェナピル（ｃｈｌｏｒｆｅｎａｐｙｌ）、［ｃ－１３．２］ＤＮＯＣ（ｄｉｎｉｔｒｏ－ｏｒｔｈｏ－ｃｒｅｓｏｌ）、［ｃ－１３．３］ビナパクリル（ｂｉｎａｐａｃｒｙｌ）、［ｃ－１３．４］スルフルラミド（ｓｕｌｆｌｕｒａｍｉｄ）等が挙げられる。 c-13: Oxidative phosphorylation uncoupling agent that disrupts the proton gradient As oxidative phosphorylation uncoupler that disrupts the proton gradient, [c-13.1] chlorfenapyr, [c-13.2] DNOC (Dini-ortho-cresol), [c-13.3] binapacryl, (c-13.4) sulfluramid and the like.
ｃ－１４：ニコチン性アセチルコリン受容体（ｎＡＣｈＲ）チャネルブロッカー
　ニコチン性アセチルコリン受容体（ｎＡＣｈＲ）チャネルブロッカーとして、［ｃ－１４．１］ベンスルタップ（ｂｅｎｓｕｌｔａｐ）、［ｃ－１４．２］カルタップ塩酸塩（ｃａｒｔａｐ　ｈｙｄｒｏｃｈｌｏｒｉｄｅ）、［ｃ－１４．３］チオシクラム（ｔｈｉｏｃｙｃｌａｍ）、［ｃ－１４．４］モノスルタップ（ｍｏｎｏｓｕｌｔａｐ）等が挙げられる。 c-14: Nicotinic acetylcholine receptor (nAChR) channel blocker [c-14.1] bensultap, [c-14.2] cartap hydrochloride (cartap) as a nicotinic acetylcholine receptor (nAChR) channel blocker hydrochloride, [c-14.3] thiocyclam, [c-14.4] monosultap, and the like.
ｃ－１５：キチン生合成阻害剤タイプ０
　キチン生合成阻害剤タイプ０として、［ｃ－１５．１］ビストリフルロン（ｂｉｓｔｒｉｆｌｕｒｏｎ）、［ｃ－１５．２］クロルフルアズロン（ｃｈｌｏｒｆｌｕａｚｕｒｏｎ）、［ｃ－１５．３］ジフルベンズロン（ｄｉｆｌｕｂｅｎｚｕｒｏｎ）、［ｃ－１５．４］フルシクロクスロン（ｆｌｕｃｙｃｌｏｘｕｒｏｎ）、［ｃ－１５．５］フルフェノクスロン（ｆｌｕｆｅｎｏｘｕｒｏｎ）、［ｃ－１５．６］ヘキサフルムロン（ｈｅｘａｆｌｕｍｕｒｏｎ）、［ｃ－１５．７］ルフェヌロン（ｌｕｆｅｎｕｒｏｎ）、［ｃ－１５．８］ノバルロン（ｎｏｖａｌｕｒｏｎ）、［ｃ－１５．９］ノビフルムロン（ｎｏｖｉｆｌｕｍｕｒｏｎ）、［ｃ－１５．１０］テフルベンズロン（ｔｅｆｌｕｂｅｎｚｕｒｏｎ）、［ｃ－１５．１１］トリフルムロン（ｔｒｉｆｌｕｍｕｒｏｎ）等が挙げられる。 c-15: chitin biosynthesis inhibitor type 0
As chitin biosynthesis inhibitor type 0, [c-15.1] bistrifluron, [c-15.2] chlorfluazuron, [c-15.3] diflubenzuron, [C-15.4] flucycloxuron, [c-15.5] flufenoxuron, [c-15.6] hexaflumuron, [c-15.7] Lufenuron, [c-15.8] novaluron, [c-15.9] noviflumuron, [c-15.10] teflubenzuron, [c-15.11] Rifurumuron (triflumuron), and the like.
ｃ－１６：キチン生合成阻害剤タイプ１
　キチン生合成阻害剤タイプ１として、［ｃ－１６．１］ブプロフェジン（ｂｕｐｒｏｆｅｚｉｎ）等が挙げられる。 c-16: Chitin biosynthesis inhibitor type 1
Examples of the chitin biosynthesis inhibitor type 1 include [c-16.1] buprofezin and the like.
ｃ－１７：ハエ目昆虫脱皮阻害剤
　ハエ目昆虫脱皮阻害剤として、［ｃ－１７．１］シロマジン（ｃｙｒｏｍａｚｉｎｅ）等が挙げられる。 c-17: Inhibitor of moltid insect molting As the insect molting inhibitor of the order Streptococcus, [c-17.1] cyromazine and the like can be mentioned.
ｃ－１８：脱皮ホルモン（エクダイソン）受容体アゴニスト
　脱皮ホルモン（エクダイソン）受容体アゴニストとして、［ｃ－１８．１］クロマフェノジド（ｃｈｒｏｍａｆｅｎｏｚｉｄｅ）、［ｃ－１８．２］ハロフェノジド（ｈａｌｏｆｅｎｏｚｉｄｅ）、［ｃ－１８．３］メトキシフェノジド（ｍｅｔｈｏｘｙｆｅｎｏｚｉｄｅ）、［ｃ－１８．４］テブフェノジド（ｔｅｂｕｆｅｎｏｚｉｄｅ）等が挙げられる。 c-18: molting hormone (ecdysone) receptor agonist As a molting hormone (ecdysone) receptor agonist, [c-18.1] chromafenozide, [c-18.2] halofenozide, [c-18] .3] methoxyphenozide, [c-18.4] tebufenozide and the like.
ｃ－１９：オクトパミン受容体アゴニスト
　オクトパミン受容体アゴニストとして、［ｃ－１９．１］アミトラズ（ａｍｉｔｒａｚ）等が挙げられる。 c-19: Octopamine receptor agonist Examples of the octopamine receptor agonist include [c-19.1] amitraz.
ｃ－２０：ミトコンドリア電子伝達系複合体ＩＩＩ阻害剤
　ミトコンドリア電子伝達系複合体ＩＩＩ阻害剤として、［ｃ－２０．１］ヒドラメチルノン（ｈｙｄｒａｍｅｔｈｙｌｎｏｎ）、［ｃ－２０．２］アセキノシル（ａｃｅｑｕｉｎｏｃｙｌ）、［ｃ－２０．３］フルアクリピリム（ｆｌｕａｃｒｙｐｙｒｉｍ）、［ｃ－２０．４］ビフェナゼート（ｂｉｆｅｎａｚａｔｅ）等が挙げられる。 c-20: mitochondrial electron transfer complex III inhibitor [c-20.1] hydramethylnon, [c-20.2] acequinocyl, [C-20.3] fluacryliprim, [c-20.4] bifenazate, and the like.
ｃ－２１：ミトコンドリア電子伝達系複合体Ｉ阻害剤（ＭＥＴＩ）
　ミトコンドリア電子伝達系複合体Ｉ阻害剤（ＭＥＴＩ）として、［ｃ－２１．１］フェナザキン（ｆｅｎａｚａｑｕｉｎ）、［ｃ－２１．２］フェンピロキシメート（ｆｅｎｐｙｒｏｘｉｍａｔｅ）、［ｃ－２１．３］ピリダベン（ｐｙｒｉｄａｂｅｎ）、［ｃ－２１．４］ピリミジフェン（ｐｙｌｉｍｉｄｉｆｅｎ）、［ｃ－２１．５］テブフェンピラド（ｔｅｂｕｆｅｎｐｙｒａｄ）、［ｃ－２１．６］トルフェンピラド（ｔｏｌｆｅｎｐｙｒａｄ）、［ｃ－２１．７］ロテノン（ｒｏｔｅｎｏｎｅ）等が挙げられる。 c-21: Mitochondrial electron transport complex I inhibitor (METI)
[C-21.1] fenazaquin, [c-21.2] fenpyroximate, [c-21.3] pyridaben, as mitochondrial electron transport system complex I inhibitors (METI); [C-21.4] pyrimidifen, [c-21.5] tebufenpyrad, [c-21.6] tolfenpyrad, [c-21.7] rotenone, and the like. Can be
ｃ－２２：電位依存性ナトリウムチャネルブロッカー
　電位依存性ナトリウムチャネルブロッカーとして、［ｃ－２２．１］インドキサカルブ（ｉｎｄｏｘａｃａｒｂ）、［ｃ－２２．２］メタフルミゾン（ｍｅｔａｆｌｕｍｉｚｏｎｅ）等が挙げられる。 c-22: Voltage-dependent sodium channel blocker Examples of the voltage-dependent sodium channel blocker include [c-22.1] indoxacarb, [c-22.2] metaflumizone, and the like.
ｃ－２３：アセチルＣｏＡカルボキシラーゼ阻害剤
　アセチルＣｏＡカルボキシラーゼ阻害剤として、［ｃ－２３．１］スピロジクロフェン（ｓｐｉｒｏｄｉｃｌｏｆｅｎ）、［ｃ－２３．２］スピロメシフェン（ｓｐｉｒｏｍｅｓｉｆｅｎ）、［ｃ－２３．３］スピロテトラマト（ｓｐｉｒｏｔｅｔｒａｍａｔ）等が挙げられる。 c-23: Acetyl-CoA carboxylase inhibitor As an acetyl-CoA carboxylase inhibitor, [c-23.1] spirodiclofen, [c-23.2] spiromesifen, [c-23.3] ] Spirotetramat and the like.
ｃ－２４：ミトコンドリア電子伝達系複合体ＩＶ阻害剤
　ミトコンドリア電子伝達系複合体ＩＶ阻害剤として、［ｃ－２４．１］リン化アルミニウム（ａｌｕｍｉｎｕｍ　ｐｈｏｓｐｈｉｄｅ）、［ｃ－２４．２］リン化カルシウム（ｃａｌｃｉｕｍ　ｐｈｏｓｐｈｉｄｅ）、［ｃ－２４．３］リン化水素（ｐｈｏｓｐｈｉｎｅ）、［ｃ－２４．４］リン化亜鉛（ｚｉｎｃ　ｐｈｏｓｐｈｉｄｅ）、［ｃ－２４．５］シアン化カルシウム（ｃａｌｃｉｕｍ　ｃｙａｎｉｄｅ）、［ｃ－２４．６］シアン化ナトリウム（ｐｏｔａｓｓｉｕｍ　ｃｙａｎｉｄｅ）、［ｃ－２４．７］シアン化カリウム（ｓｏｄｉｕｍ　ｃｙａｎｉｄｅ）等が挙げられる。 c-24: Mitochondrial electron transport system complex IV inhibitor [c-24.1] aluminum phosphide (aluminum phosphide), [c-24.2] calcium phosphate ( calcium phosphate, [c-24.3] hydrogen phosphide (phosphine), [c-24.4] zinc phosphide (zinc phosphide), [c-24.5] calcium cyanide, [c −24.6] sodium cyanide (potassium cyanide), [c-24.7] potassium cyanide, and the like.
ｃ－２５：ミトコンドリア電子伝達系複合体ＩＩ阻害剤
　ミトコンドリア電子伝達系複合体ＩＩ阻害剤として、［ｃ－２５．１］シエノピラフェン（ｃｙｅｎｏｐｙｒａｆｅｎ）、［ｃ－２５．２］シフルメトフェン（ｃｙｆｌｕｍｅｔｏｆｅｎ）、［ｃ－２５．３］ピフルブミド（ｐｙｆｌｕｂｕｍｉｄｅ）等が挙げられる。 c-25: mitochondrial electron transport system complex II inhibitor [c-25.1] cyenopyrafen, [c-25.2] cyflumetofen, [c-25.1] cyenopyrafen -25.3] piflubumide and the like.
ｃ－２６：リアノジン受容体モジュレーター
　リアノジン受容体モジュレーターとして、［ｃ－２６．１］クロラントラニリプロール（ｃｈｌｏｒａｎｔｒａｎｉｌｉｐｒｏｌｅ）、［ｃ－２６．２］シアントラニリプロール（ｃｙａｎｔｒａｎｉｌｉｐｒｏｌｅ）、［ｃ－２６．３］フルベンジアミド（ｆｌｕｂｅｎｄｉａｍｉｄｅ）等が挙げられる。 c-26: Ryanodine receptor modulator As the ryanodine receptor modulator, [c-26.1] chlorantraniliprole, [c-26.2] cyanantraniprole, [c-26. 3] flubendiamide and the like.
ｃ－２７：標的部位未特定の弦音器官モジュレーター
　標的部位未特定の弦音器官モジュレーターとして、［ｃ－２７．１］フロニカミド（ｆｌｏｎｉｃａｍｉｄ）等が挙げられる。 c-27: String Organ Modulator with Unspecified Target Sites Examples of string organ modulators with unspecified target sites include [c-27.1] flonicamid.
ｃ－２８：その他の殺虫剤
　その他の殺虫剤として、［ｃ－２８．１］アザジラクチン（ａｚａｄｉｒａｃｈｔｉｎ）、［ｃ－２８．２］ベンゾキシメート（ｂｅｎｚｏｘｉｍａｔｅ）、［ｃ－２８．３］フェニソブロモレート（ｐｈｅｎｉｓｏｂｒｏｍｏｌａｔｅ）、［ｃ－２８．４］キノメチオナート（ｃｈｉｎｏｍｅｔｈｉｏｎａｔ）、［ｃ－２８．５］ジコホル（ｄｉｃｏｆｏｌ）、［ｃ－２８．６］ピリダリル（ｐｙｒｉｄａｌｙｌ）、［ｃ－２８．７］ブロモプロピレート（ｂｒｏｍｏｐｒｏｐｙｌａｔｅ）、［ｃ－２８．８］トリアザメート（ｔｒｉａｚａｍａｔｅ）、［ｃ－２８．９］ジシクラニル（ｄｉｃｙｃｌａｎｉｌ）、［ｃ－２８．１０］ジノブトン（ｄｉｎｏｂｕｔｏｎ）、［ｃ－２８．１１］ジノカップ（ｄｉｎｏｃａｐ）、［ｃ－２８．１２］シアン化水素（ｈｙｄｒｏｇｅｎ　ｃｙａｎｉｄｅ）、［ｃ－２８．１３］ヨウ化メチル（ｍｅｔｈｙｌ ｉｏｄｉｄｅ）、［ｃ－２８．１４］カランジン（ｋａｒａｎｊｉｎ）、［ｃ－２８．１５］塩化水銀（ｍｅｒｃｕｒｙ　ｃｈｌｏｒｉｄｅ）、［ｃ－２８．１６］メチルイソチオシアネート（ｍｅｔｈｙｌ　ｉｓｏｔｈｉｏｃｙａｎａｔｅ）、［ｃ－２８．１７］ペンタクロロフェノール（ｐｅｎｔａｃｈｌｏｒｏｐｈｅｎｏｌ）、［ｃ－２８．１８］ホスフィン（ｐｈｏｓｐｈｉｎｅ）、［ｃ－２８．１９］ピペロニル　ブトキシド（ｐｉｐｅｒｏｎｙｌ ｂｕｔｏｘｉｄｅ）、［ｃ－２８．２０］ポリナクチン複合体（ｐｏｌｙｎａｃｔｉｎｓ）、［ｃ－２８．２１］サバディラ（ｓａｂａｄｉｌｌａ）、［ｃ－２８．２２］スルコフロン塩（スルコフロン－ナトリウム（ｓｕｌｃｏｆｕｒｏｎ－ｓｏｄｉｕｍ））、［ｃ－２８．２３］トリブホス（ｔｒｉｂｕｆｏｓ）、［ｃ－２８．２４］アルドリン（ａｌｄｒｉｎ）、［ｃ－２８．２５］アミジチオオン（ａｍｉｄｉｔｈｉｏｎ）、［ｃ－２８．２６］アミドチオエート（ａｍｉｄｏｔｈｉｏａｔｅ）、［ｃ－２８．２７］アミノカルブ（ａｍｉｎｏｃａｒｂ）、［ｃ－２８．２８］アミトン（ａｍｉｔｏｎ）、［ｃ－２８．２９］アラマイト（ａｒａｍｉｔｅ）、［ｃ－２８．３０］アチダチオン（ａｔｈｉｄａｔｈｉｏｎ）、［ｃ－２８．３１］アゾトエート（ａｚｏｔｈｏａｔｅ）、［ｃ－２８．３２］ポリスルフィドバリウム（ｂａｒｉｕｍ　ｐｏｌｙｓｕｌｐｈｉｄｅ）、［ｃ－２８．３３］ベンクロチアズ（ｂｅｎｃｌｏｔｈｉａｚ）、［ｃ－２８．３４］５－（１，３－ベンゾジオキソール－５－イル）－３－ヘキシルシクロヘキサ－２－エノン（５－（１，３－ｂｅｎｚｏｄｉｏｘｏｌｅ－５－ｙｌ）－３－ｈｅｘｙｌｃｙｃｌｏｈｅｘａ－２－ｅｎｏｎｅ）、［ｃ－２８．３５］１，１－ビス（４－クロロフェニル）－２－エトキシエタノール（１，１－ｂｉｓ（４－ｃｈｌｏｒｏｐｈｅｎｙｌ）－２－ｅｔｈｏｘｙｅｔｈａｎｏｌ）、［ｃ－２８．３６］ブトネート（ｂｕｔｏｎａｔｅ）、［ｃ－２８．３７］ブトピロノキシル（ｂｕｔｏｐｙｒｏｎｏｘｙｌ）、［ｃ－２８．３８］２－（２－ブトキシエトキシ）エチル　チオシアナート（２－（２－ｂｕｔｏｘｙｅｔｈｏｘｙ）ｅｔｈｙｌ　ｔｈｉｏｃｙａｎａｔｅ）、［ｃ－２８．３９］カンフェクロル（ｃａｍｐｈｅｃｈｌｏｒ）、［ｃ－２８．４０］クロルベンシド（ｃｈｌｏｒｂｅｎｓｉｄｅ）、［ｃ－２８．４１］クロルデコン（ｃｈｌｏｒｄｅｃｏｎｅ）、［ｃ－２８．４２］クロルジメホルム（ｃｈｌｏｒｄｉｍｅｆｏｒｍ）、［ｃ－２８．４３］クロルフェネトール（ｃｈｌｏｒｆｅｎｅｔｈｏｌ）、［ｃ－２８．４４］クロルフェンソン（ｃｈｌｏｒｆｅｎｓｏｎ）、［ｃ－２８．４５］フルアズロン（ｆｌｕａｚｕｒｏｎ）、［ｃ－２８．４６］メタアルデヒド（ｍｅｔａｌｄｅｈｙｄｅ）、［ｃ－２８．４７］ビアラホス（ｂｉａｌａｐｈｏｓ）、［ｃ－２８．４８］塩酸レバミゾール（ｌｅｖａｍｉｓｏｌ）、［ｃ－２８．４９］アミドフルメト（ａｍｉｄｏｆｌｕｍｅｔ）、［ｃ－２８．５０］ピラフルプロール（ｐｙｒａｆｌｕｐｒｏｌｅ）、［ｃ－２８．５１］ピリプロール（ｐｙｒｉｐｒｏｌｅ）、［ｃ－２８．５２］トラロピリル（ｔｒａｌｏｐｙｒｉｌ）、［ｃ－２８．５３］フルピラゾフォス（ｆｌｕｐｙｒａｚｏｆｏｓ）、［ｃ－２８．５４］ジオフェノラン（ｄｉｏｆｅｎｏｌａｎ）、［ｃ－２８．５５］クロルベンジレート（ｃｈｌｏｒｏｂｅｎｚｉｌａｔｅ）、［ｃ－２８．５６］フルフェンジン（ｆｌｕｆｅｎｚｉｎｅ）、［ｃ－２８．５７］ベンゾメート（ｂｅｎｚｏｍａｔｅ）、［ｃ－２８．５８］フルフェネリム（ｆｌｕｆｅｎｅｒｉｍ）、［ｃ－２８．５９］アルベンダゾール（ａｌｂｅｎｄａｚｏｌｅ）、［ｃ－２８．６０］オキシベンダゾール（ｏｘｉｂｅｎｄａｚｏｌｅ）、［ｃ－２８．６１］フェンベンダゾール（ｆｅｎｂｅｎｄａｚｏｌｅ）、［ｃ－２８．６２］メタム・ナトリウム（ｍｅｔａｍ－ｓｏｄｉｕｍ）、［ｃ－２８．６３］１，３－ジクロロプロペン（１，３－ｄｉｃｈｌｏｒｏｐｒｏｐｅｎｅ）、［ｃ－２８．６４］フロメトキン（ｆｌｏｍｅｔｏｑｕｉｎ）、［ｃ－２８．６５］シクラニリプロール（ｃｙｃｌａｎｉｌｉｐｒｏｌｅ）、［ｃ－２８．６６］テトラニリプロール（ｔｅｔｒａｎｉｌｉｐｒｏｌｅ）、［ｃ－２８．６７］ブロフラニリド（ｂｒｏｆｌａｎｉｌｉｄｅ）、［ｃ－２８．６８］ジクロロメゾチアズ（ｄｉｃｌｏｒｏｍｅｚｏｔｉａｚ）、［ｃ－２８．６９］エチレンジブロマイド（ｅｔｈｙｌｅｎｅ　ｄｉｂｒｏｍｉｄｅ）、［ｃ－２８．７０］アクリロニトリル（ａｃｒｙｌｏｎｉｔｒｉｌｅ）、［ｃ－２８．７１］ビス（２－クロロエチル）エーテル（ｂｉｓ（２－ｃｈｌｏｒｏｅｔｈｙｌ）ｅｔｈｅｒ）、［ｃ－２８．７２］１－ブロモ－２－クロロエタン（１－ｂｒｏｍｏ－２－ｃｈｌｏｒｏｅｔｈａｎｅ）、［ｃ－２８．７３］３－ブロモ－１－クロロプロパ－１－エン（３－ｂｒｏｍｏ－１－ｃｈｌｏｒｏｐｒｏｐ－１－ｅｎｅ）、［ｃ－２８．７４］ブロモシクレン（ｂｒｏｍｏｃｙｃｌｅｎ）、［ｃ－２８．７５］二硫化炭素（ｃａｒｂｏｎ　ｄｉｓｕｌｆｉｄｅ）、［ｃ－２８．７６］四塩化炭素（ｔｅｔｒａｃｈｌｏｒｏｍｅｔｈａｎｅ）、［ｃ－２８．７７］ネマデクチン（ｎｅｍａｄｅｃｔｉｎ）、［ｃ－２８．７８］シミアゾール（ｃｙｍｉａｚｏｌｅ）［ｃ－２８．７９］カルシウム　ポリスルフィド（ｃａｌｃｉｕｍ　ｐｏｌｙｓｕｌｆｉｄｅ）、［ｃ－２８．８０］サイトカイニン（ｃｙｔｏｋｉｎｉｎ）、［ｃ－２８．８１］２－（オクチルチオ）エタノール、［ｃ－２８．８２］オレイン酸カリウム（ｐｏｔａｓｓｉｕｍ　ｏｌｅａｔｅ）、［ｃ－２８．８３］オレイン酸ナトリウム（ｓｏｄｉｕｍ　ｏｌｅａｔｅ）、［ｃ－２８．８４］マシン油（ｍａｃｈｉｎｅ　ｏｉｌ）、［ｃ－２８．８５］タール油（ｔａｒ　ｏｉｌ）、［ｃ－２８．８６］アナバシン（ａｎａｂａｓｉｎｅ）、［ｃ－２８．８７］酒石酸モランテル（ｍｏｒａｎｔｅｌ　ｔａｒｔｒａｔｅ）、［ｃ－２８．８８］除虫菊（ピレトリン（ｐｙｒｅｔｈｒｕｍ））、［ｃ－２８．８９］ナタネ油（ｒａｐｅ　ｓｅｅｄ　ｏｉｌ）、［ｃ－２８．９０］ダイズレチシン（ｓｏｙｂｅａｎ　ｌｅｃｉｔｈｉｎ）、［ｃ－２８．９１］デンプン（ｓｔａｒｃｈ）、［ｃ－２８．９２］ヒドロキシプロピルデンプン（ｈｙｄｒｏｘｙｐｒｏｐｙｌｓｔａｒｃｈ）、［ｃ－２８．９３］脂肪酸グリセリド（ｄｅｃａｎｏｙｌｏｃｔａｎｏｙｌｇｌｙｃｅｒｏｌ）、［ｃ－２８．９４］プロピレングリコールモノ脂肪酸エステル（ｐｒｏｐｙｌｅｎｅ　ｇｌｙｃｏｌ　ｆａｔｔｙ　ａｃｉｄ　ｅｓｔｅｒ）、［ｃ－２８．９５］ケイソウ土（ｄｉａｔｏｍｉｔｅ）、［ｃ－２８．９６］アフォキソラネル（ａｆｏｘｏｌａｎｅｒ）、［ｃ－２８．９７］フルアザインドリジン（ｆｌｕａｚａｉｎｄｏｌｉｚｉｎｅ）、［ｃ－２８．９８］アフィドピロペン（ａｆｉｄｏｐｙｒｏｐｅｎ）、［ｃ－２８．９９］シハロジアミド（ｃｙｈａｌｏｄｉａｍｉｄｅ）、［ｃ－２８．１００］チオキサザフェン（ｔｉｏｘａｚａｆｅｎ）、［ｃ－２８．１０１］フルヘキサフォン（ｆｌｕｈｅｘａｆｏｎ）、［ｃ－２８．１０２］フルララネル（ｆｌｕｒａｌａｎｅｒ）、［ｃ－２８．１０３］フルキサメタミド（ｆｌｕｘａｍｅｔａｍｉｄｅ）、［ｃ－２８．１０４］テトラクロラントラニリプロール（ｔｅｔｒａｃｈｌｏｒａｎｔｒａｎｉｌｉｐｒｏｌｅ）、［ｃ－２８．１０５］サロラネル（ｓａｒｏｌａｎｅｒ）、［ｃ－２８．１０６］ロチラネル（ｌｏｔｉｌａｎｅｒ）、［ｃ－２８．１０７］シクロキサプリド（ｃｙｃｌｏｘａｐｒｉｄ）、［ｃ－２８．１０８］フルエンスルホン（ｆｌｕｅｎｓｕｌｆｏｎｅ）、［ｃ－２８．１０９］ＴＰＩＣ（ｔｒｉｐｒｏｐｙｌ　ｉｓｏｃｙａｎｕｒａｔｅ）、［ｃ－２８．１１０］Ｄ－Ｄ（１，３－Ｄｉｃｈｌｏｒｏｐｒｏｐｅｎｅ）、［ｃ－２８．１１１］ペルオキソカルボナート（ｐｅｒｏｘｏｃａｒｂｏｎａｔｅ）、［ｃ－２８．１１２］ＭＢ－５９９（ｖｅｒｂｕｔｉｎ）、［ｃ－２８．１１３］ビス（２，３，３，３－テトラクロロプロピル）エーテル（ｂｉｓ（２，３，３，３－ｔｅｔｒａｃｈｌｏｒｏｐｒｏｐｙｌ） ｅｔｈｅｒ）、［ｃ－２８．１１４］ＤＣＩＰ（ｂｉｓ（２－ｃｈｌｏｒｏ－１－ｍｅｔｈｙｌｅｔｈｙｌ）ｅｔｈｅｒ）、［ｃ－２８．１１５］ＥＮＴ－８１８４（Ｎ－（２－Ｅｔｈｙｌｈｅｘｙｌ）ｂｉｃｙｃｌｏ［２．２．１］ｈｅｐｔ－５－ｅｎｅ－２,３－ｄｉｃａｒｂｏｘｉｍｉｄｅ）、［ｃ－２８．１１６］Ｂａｙｅｒ　２２４０８（Ｏ,Ｏ－ｄｉｅｔｈｙｌ Ｏ－ｎａｐｈｔｈａｌｉｍｉｄｏ ｐｈｏｓｐｈｏｒｏｔｈｉｏａｔｅ）、［ｃ－２８．１１７］Ｂａｙｅｒ　３２３９４（ｔｒｉｓ（１－ｄｏｄｅｃｙｌ－３－ｍｅｔｈｙｌ－２－ｐｈｅｎｙｌｂｅｎｚｉｍｉｄａｚｏｌｉｕｍ）ｈｅｘａｃｙａｎｏｆｅｒｒａｔｅ）、 c-28: Other insecticides [c-28.1] azadirachtin, [c-28.2] benzoximate, [c-28.3] phenisobromo Phenisobromolate, [c-28.4] quinomethionate, [c-28.5] dicofol, [c-28.6] pyridalyl, [c-28.7] bromopropylate Brompropylate, [c-28.8] triazamate, [c-28.9] dicyclanil, [c-28.10] dinobuton, [c-28.11] dinocup ( din ocap), [c-28.12] hydrogen cyanide, [c-28.13] methyl iodide, [c-28.14] Karanjin, [c-28.15] Mercury chloride, [c-28.16] methyl isothiocyanate, [c-28.17] pentachlorophenol, [c-28.18] phosphine, [c -28.19] piperonyl butoxide, [c-28.20] polynactin complexes, [c-28.21] sabadilla [C-28.22] sulcofuron salt (sulcofuron-sodium), [c-28.23] tribubufos, [c-28.24] aldrin, [c-28.25] Amidithione, [c-28.26] amidothioate, [c-28.27] aminocarb, [c-28.28] amiton, [c-28.29] Aramite, [c-28.30] athidathion, [c-28.31] azotoate, [c-28.32] polysulfide barium (barium polysulphide), [c- 8.33] benclothiaz, [c-28.34] 5- (1,3-benzodioxol-5-yl) -3-hexylcyclohex-2-enone (5- (1,3- benzodioxole-5-yl) -3-hexylcyclohexa-2-enone), [c-28.35] 1,1-bis (4-chlorophenyl) -2-ethoxyethanol (1,1-bis (4-chlorophenyl)-) 2-ethyethanol, [c-28.36] butonate, [c-28.37] butopyronoxyl, [c-28.38] 2- (2-butoxyethoxy) ethyl thiocyanate (2- ( 2-butyethoxy) ethyl thiocyan ate), [c-28.39] camphechlor, [c-28.40] chlorbenside, [c-28.41] chlordecone, [c-28.42] chlordiforme , [C-28.43] chlorphenetol, [c-28.44] chlorphenson, [c-28.45] fluazuron, [c-28.46] methaldehyde (Metaldehyde), [c-28.47] bialaphos, [c-28.48] levamisol hydrochloride, [c-28.49] amidoflumet , [C-28.50] pyrafluprole, [c-28.51] pyriprole, [c-28.52] tralopyryl, [c-28.53] flupyrazofos , [C-28.54] diophenolan, [c-28.55] chlorobenzilate, [c-28.56] flufenzine, [c-28.57] benzomate , [C-28.58] flufenerim, [c-28.59] albendazole, [c-28.60] oxybendazole , [C-28.61] fenbendazole, [c-28.62] metam-sodium, [c-28.63] 1,3-dichloropropene (1,3-dichloropropene) ), [C-28.64] flometoquin, [c-28.65] cyclaniliprole, [c-28.66] tetranyliprole, [c-28.67] Brofuranilide, [c-28.68] dichloromezzotiaz, [c-28.69] Ethylene dibromide, [c-28.70] acrylonitrile acrylonitrile), [c-28.71] bis (2-chloroethyl) ether, [c-28.72] 1-bromo-2-chloroethane (1-bromo-2-chloroethane) , [C-28.73] 3-bromo-1-chloroprop-1-ene, [c-28.74] bromocyclen, [c-28.73] 75] carbon disulphide, [c-28.76] tetrachloromethane, [c-28.77] nemadectin, [c-28.78] cymizazole [c- 28.79] F Calcium polysulfide, [c-28.80] cytokinin, [c-28.81] 2- (octylthio) ethanol, [c-28.82] Potassium oleate, [c -28.83] sodium oleate, [c-28.84] machine oil, [c-28.85] tar oil, [c-28.86] anabacine ( anabasine), [c-28.87] morantel tartrate, [c-28.88] pyrethrum (pyrethrum), [c-28.89] rapeseed oil, [c- 28.90 Soybean lectin, [c-28.91] starch, [c-28.92] hydroxypropyl starch, [c-28.93] fatty acid glyceride (decanoylcanoylglycerol-28) .94] propylene glycol monofatty acid ester, [c-28.95] diatomite, [c-28.96] afoxolaner, [c-28.97] fluaza Fluazaindolizine, [c-28.98] aphidopyopen, [c-28.99] Halodiamide, [c-28.100] thioxazafen, [c-28.101] fluhexafon, [c-28.102] fluralaner, [c-28.103] Fluxametamide, [c-28.104] tetrachlorantraniliprole, [c-28.105] saloraner, [c-28.106] lotilaner, [c-28] .107] cycloxapride, [c-28.108] fluensulfone, [c-28.109] TPIC ( tripropyl isocyanurate), [c-28.110] DD (1,3-dichloropropene), [c-28.111] peroxocarbonate, [c-28.112] MB-599 (verbutin), [C-28.113] bis (2,3,3,3-tetrachloropropyl) ether (bis (2,3,3,3-tetrachloropropyl) ether), [c-28.114] DCIP (bis (2 -Chloro-1-methylethyl) ether), [c-28.115] ENT-8184 (N- (2-Ethylhexyl) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide), [ c-28.1 6] Bayer 22408 (O, O-diethyl O-naphthalimido phosphorothioate), [c-28.117] Bayer 32394 (tris (1-dodecyl-3-methyl-2-phenylbenzimidazolium) hexacyanoferrate),
［ｃ－２８．１１８］式（ｓ３４）
Figure JPOXMLDOC01-appb-C000110
で表される化合物（国際公開第１０／０５１９２６号参照）、 [C-28.118] Equation (s34)
Figure JPOXMLDOC01-appb-C000110
(See WO10 / 051926),
［ｃ－２８．１１９］式（ｓ３５）
Figure JPOXMLDOC01-appb-C000111
で表される化合物（国際公開第１３／１１５３９１号参照）、 [C-28.119] Formula (s35)
Figure JPOXMLDOC01-appb-C000111
(See WO 13/115391),
［ｃ－２８．１２０］式（ｓ３６）
Figure JPOXMLDOC01-appb-C000112
で表される化合物（国際公開第１２／０２９６７２号参照）、 [C-28.120] Equation (s36)
Figure JPOXMLDOC01-appb-C000112
A compound represented by the formula (see International Publication No. 12/029672):
［ｃ－２８．１２１］式（ｓ３７）
Figure JPOXMLDOC01-appb-C000113
で表される化合物（国際公開第０６／０５６１０８号参照）、 [C-28.121] Equation (s37)
Figure JPOXMLDOC01-appb-C000113
(See WO06 / 056108),
［ｃ－２８．１２２］式（ｓ３８）
Figure JPOXMLDOC01-appb-C000114
で表される化合物（国際公開第１４／０５３４５０号、国際特許第１５／１４４６８３号参照）、 [C-28.122] Equation (s38)
Figure JPOXMLDOC01-appb-C000114
(See WO 14/053450, WO 15/144683);
［ｃ－２８．１２３］式（ｓ３９）
Figure JPOXMLDOC01-appb-C000115
で表される化合物（国際公開第１４／０５３４５０号、国際特許第１５／１４４６８３号参照）、 [C-28.123] Formula (s39)
Figure JPOXMLDOC01-appb-C000115
(See WO 14/053450, WO 15/144683);
［ｃ－２８．１２４］式（ｓ４０）
Figure JPOXMLDOC01-appb-C000116
で表される化合物（国際公開第１４／０５３４５０号、国際特許第１５／１４４６８３号参照）、 [C-28.124] Equation (s40)
Figure JPOXMLDOC01-appb-C000116
(See WO 14/053450, WO 15/144683);
［ｃ－２８．１２５］式（ｓ４１）
Figure JPOXMLDOC01-appb-C000117
［式中、ｍ６は、０～２の整数を表す。］で表される化合物（国際公開第１０／１２９４９７号参照）、 [C-28.125] Formula (s41)
Figure JPOXMLDOC01-appb-C000117
[In the formula, m6 represents an integer of 0 to 2. (See WO 10/129497),
［ｃ－２８．１２６］式（ｓ４２）
Figure JPOXMLDOC01-appb-C000118
［式中、ｍ７は、０～２の整数を表す。］で表される化合物（国際公開第１１／１５２３２０号参照）、 [C-28.126] Equation (s42)
Figure JPOXMLDOC01-appb-C000118
[In the formula, m7 represents an integer of 0 to 2. (See WO 11/152320),
［ｃ－２８．１２７］式（ｓ４３）
Figure JPOXMLDOC01-appb-C000119
［式中、ｍ８は、０～２の整数を表す。］で表される化合物（特開平２７―１６０８１３号公報参照）、 [C-28.127] Equation (s43)
Figure JPOXMLDOC01-appb-C000119
[In the formula, m8 represents an integer of 0 to 2. ] (See JP-A-27-160813);
［ｃ－２８．１２８］式（ｓ４４）
Figure JPOXMLDOC01-appb-C000120
［式中、Ａ５２は、水素原子、またはフッ素原子を表す。］で表される化合物（国際公開第１１／１３４９６４号、国際特許第１４／００５９８２号参照）、 [C-28.128] Equation (s44)
Figure JPOXMLDOC01-appb-C000120
[Wherein, A52 represents a hydrogen atom or a fluorine atom. (See WO 11/134964, WO 14/005982),
［ｃ－２８．１２９］式（ｓ４５）
Figure JPOXMLDOC01-appb-C000121
［式中、ｍ９は、０～２の整数を表し、Ａ５３は、フッ素原子、または塩素原子を表す。］で表される化合物（国際公開第１５／０２５８２６号参照）、 [C-28.129] Equation (s45)
Figure JPOXMLDOC01-appb-C000121
[In the formula, m9 represents an integer of 0 to 2, and A53 represents a fluorine atom or a chlorine atom. (See WO 15/025826),
［ｃ－２８．１３０］式（ｓ４６）
Figure JPOXMLDOC01-appb-C000122
［式中、Ｖ３は、窒素原子、炭素原子、またはＣ－Ｆを表し、Ｖ４およびＶ５は、それぞれ独立していて、窒素原子、または炭素原子を表す。］で表される化合物（国際公開第１１／１３４９６４号、国際公開第１４／００５９８２号参照）、 [C-28.130] Equation (s46)
Figure JPOXMLDOC01-appb-C000122
[Wherein, V3 represents a nitrogen atom, a carbon atom, or CF, and V4 and V5 each independently represent a nitrogen atom or a carbon atom. (See WO 11/134964, WO 14/005982),
［ｃ－２８．１３１］式（ｓ４７）
Figure JPOXMLDOC01-appb-C000123
［式中、Ａ５４は、水素原子、メチル基、メトキシ基、またはエトキシ基を表し、Ａ５５は、塩素原子、またはメチル基を表し、Ａ５６は、メチル基、またはエチル基を表す。］で表される化合物（国際公開第０９／０４９８５１号参照）、 [C-28.131] Formula (s47)
Figure JPOXMLDOC01-appb-C000123
[In the formula, A54 represents a hydrogen atom, a methyl group, a methoxy group, or an ethoxy group, A55 represents a chlorine atom or a methyl group, and A56 represents a methyl group or an ethyl group. (See WO09 / 049851),
［ｃ－２８．１３２］式（ｓ４８）
Figure JPOXMLDOC01-appb-C000124
［式中、Ａ５７は、水素原子、フッ素原子、または塩素原子を表し、Ａ５８は、
Figure JPOXMLDOC01-appb-C000125
からなる群から選択される１種の部分構造を表す。］で表される化合物（国際公開第１１／０６７２７２号参照）、 [C-28.132] Formula (s48)
Figure JPOXMLDOC01-appb-C000124
[Wherein, A57 represents a hydrogen atom, a fluorine atom, or a chlorine atom;
Figure JPOXMLDOC01-appb-C000125
Represents one kind of partial structure selected from the group consisting of: A compound represented by the formula (see International Publication No. 11/067272):
［ｃ－２８．１３３］式（ｓ４９）
Figure JPOXMLDOC01-appb-C000126
［式中、Ａ５９は、水素原子、フッ素原子、または塩素原子を表し、Ａ６０は、
Figure JPOXMLDOC01-appb-C000127
からなる群から選択される部分構造を表す。］で表される化合物（国際公開第１０／０９０３４４号参照）、 [C-28.133] Equation (s49)
Figure JPOXMLDOC01-appb-C000126
[Wherein, A59 represents a hydrogen atom, a fluorine atom, or a chlorine atom;
Figure JPOXMLDOC01-appb-C000127
Represents a partial structure selected from the group consisting of (See WO 10/090344),
［ｃ－２８．１３４］式（ｓ５０）
Figure JPOXMLDOC01-appb-C000128
［式中、ｍ１０は、０～２の整数を表し、Ａ６１は、トリフルオロメチル基、トリフルオロメチルチオ基、トリフルオロメチルスルフィニル基、またはトリフルオロメチルスルホニル基を表し、Ａ６２は、水素原子、またはトリフルオロメチル基を表し、Ｖ６は、窒素原子、または炭素原子を表し、Ｖ７は、酸素原子、またはＮ－メチル基を表す。］で表される化合物（国際公開第１４／１０４４０７号参照）、 [C-28.134] Formula (s50)
Figure JPOXMLDOC01-appb-C000128
[In the formula, m10 represents an integer of 0 to 2, A61 represents a trifluoromethyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, and A62 represents a hydrogen atom or Represents a trifluoromethyl group, V6 represents a nitrogen atom or a carbon atom, and V7 represents an oxygen atom or an N-methyl group. (See WO 14/104407),
［ｃ－２８．１３５］式（ｓ５１）
Figure JPOXMLDOC01-appb-C000129
［式中、Ａ６３は、水素原子、またはフッ素原子を表し、アミド基は４位、または５位に結合し、Ａ６４は、
Figure JPOXMLDOC01-appb-C000130
からなる群から選択される部分構造を表す。］で表される化合物（国際公開第１５／０３８５０３号、国際特許第１６／１４４３５１号、国際特許第１６／１４４６７８号参照）、 [C-28.135] Equation (s51)
Figure JPOXMLDOC01-appb-C000129
[Wherein, A63 represents a hydrogen atom or a fluorine atom, the amide group is bonded to the 4- or 5-position, and A64 is
Figure JPOXMLDOC01-appb-C000130
Represents a partial structure selected from the group consisting of (See WO 15/038503, WO 16/144351, WO 16/144678),
［ｃ－２８．１３６］式（ｓ５２）
Figure JPOXMLDOC01-appb-C000131
［式中、Ａ６５は、水素原子、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、Ａ６６は、水素原子、ハロゲン原子、またはＣ１～Ｃ６のアルキル基を表し、Ａ６７およびＡ６８は、それぞれ独立していて、水素原子、シアノ基で適宜置換されてもよいＣ１～Ｃ６のアルキル基、メトキシ基で適宜置換されてもよいアルキル基、エトキシ基で適宜置換されてもよいアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表し、
Ａ６９は、水素原子、シアノ基、シアノ基で適宜置換されてもよいＣ１～Ｃ６のハロアルキル基、Ｃ１～Ｃ６のアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。］で表される化合物（国際公開第１２／１４３３１７号、国際特許第１６／０１６３６９号参照）、 [C-28.136] Equation (s52)
Figure JPOXMLDOC01-appb-C000131
[Wherein, A65 represents a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group, A66 represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group, and A67 and A68 represent Each independently being a hydrogen atom, a C1-C6 alkyl group optionally substituted with a cyano group, an alkyl group optionally substituted with a methoxy group, an alkyl group optionally substituted with an ethoxy group, Or a C3-C8 cycloalkyl group,
A69 represents a hydrogen atom, a cyano group, a C1 to C6 haloalkyl group optionally substituted with a cyano group, a C1 to C6 alkyl group, or a C3 to C8 cycloalkyl group. (See WO 12/143317, WO 16/016369),
［ｃ－２８．１３７］式（ｓ５３）または式（ｓ５４）
Figure JPOXMLDOC01-appb-C000132
［式中、Ａ７０は、メチル基、エチル基、イソプロピル基、２，２，２－トリフルオロエチル基、またはフェニル基を表し、Ａ７１は、
Figure JPOXMLDOC01-appb-C000133
からなる群から選択される部分構造を表し、Ａ７２は、
Figure JPOXMLDOC01-appb-C000134
からなる群から選択される部分構造を表し、Ｖ８は、酸素原子、硫黄原子、－ＣＨ２－、または－ＣＨ２ＣＨ２－を表す。］で表される化合物（国際公開第１４／１６７０８４号、国際特許第１６／０５５４３１号参照）、 [C-28.137] Formula (s53) or formula (s54)
Figure JPOXMLDOC01-appb-C000132
Wherein A 70 represents a methyl group, an ethyl group, an isopropyl group, a 2,2,2-trifluoroethyl group, or a phenyl group;
Figure JPOXMLDOC01-appb-C000133
A72 represents a partial structure selected from the group consisting of:
Figure JPOXMLDOC01-appb-C000134
And V8 represents an oxygen atom, a sulfur atom, —CH 2 —, or —CH 2 CH 2 —. (See International Publication No. 14/167084, International Patent Publication No. 16/055431),
［ｃ－２８．１３８］式（ｓ５５）
Figure JPOXMLDOC01-appb-C000135
［式中、ｍ１１は、０～１の整数を表し、Ａ７３は、塩素原子、臭素原子、メチル基、またはトリフルオロメチル基を表し、Ａ７４は、水素原子、塩素原子、臭素原子、シアノ基、またはトリフルオロメチル基表し、Ａ７５は、水素原子、塩素原子または臭素原子を表し、Ａ７６およびＡ７７は、それぞれ独立していて、Ｃ１～Ｃ６のアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表し、Ａ７８は、塩素原子、臭素原子、シアノ基、ニトロ基、ジフルオロメチル基、またはトリフルオロメチル基を表す。］で表される化合物（国際公開第１３／０２４００９号参照）、 [C-28.138] Equation (s55)
Figure JPOXMLDOC01-appb-C000135
[Wherein, m11 represents an integer of 0 to 1, A73 represents a chlorine atom, a bromine atom, a methyl group, or a trifluoromethyl group, A74 represents a hydrogen atom, a chlorine atom, a bromine atom, a cyano group, A75 represents a hydrogen atom, a chlorine atom or a bromine atom; A76 and A77 each independently represent a C1-C6 alkyl group or a C3-C8 cycloalkyl group; A78 represents a chlorine atom, a bromine atom, a cyano group, a nitro group, a difluoromethyl group, or a trifluoromethyl group. A compound represented by the formula:
［ｃ－２８．１３９］式（ｓ５６）
Figure JPOXMLDOC01-appb-C000136
［式中、Ａ７９、Ａ８０、Ａ８１およびＡ８２は、それぞれ独立していて、水素原子、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ１～Ｃ６のアルコキシ基、またはＣ３～Ｃ８のシクロアルコキシ基を表す。］で表される化合物（国際公開第１２／０２７５２１号参照）、 [C-28.139] Formula (s56)
Figure JPOXMLDOC01-appb-C000136
[Wherein A79, A80, A81 and A82 are each independently a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, or a C3-C8 Represents a cycloalkoxy group. (See WO 12/027521),
［ｃ－２８．１４０］式（ｓ５７）
Figure JPOXMLDOC01-appb-C000137
［式中、ｍ１２は、０～２の整数を表し、Ａ８３は、水素原子、またはフッ素原子を表し、Ａ８４は、
Figure JPOXMLDOC01-appb-C000138
からなる群から選択される部分構造を表す。］で表される化合物（国際公開第１３／１６２７１５号参照）、 [C-28.140] Equation (s57)
Figure JPOXMLDOC01-appb-C000137
[In the formula, m12 represents an integer of 0 to 2, A83 represents a hydrogen atom or a fluorine atom, and A84 represents
Figure JPOXMLDOC01-appb-C000138
Represents a partial structure selected from the group consisting of (See WO 13/162715),
［ｃ－２８．１４１］アシノナピル（ａｃｙｎｏｎａｐｙｒ）、 [C-28.141] asynonapyr,
［ｃ－２８．１４２］式（ｓ５９）
Figure JPOXMLDOC01-appb-C000139
［Ａ９０は、ハロゲン原子、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表し、Ａ９１は、Ｃ１～Ｃ６のハロアルキル基を表し、Ａ９２およびＡ９３は、それぞれ独立していて、水素原子、Ｃ１～Ｃ６のアルキル基、アセチル基、プロピオノイル基、メタンスルホニルエチル基、メトキシカルボニル基、またはエトキシカルボニル基を表し、Ａ９４およびＡ９５は、それぞれ独立していて、水素原子、Ｃ１～Ｃ６のアルキル基、またはＣ１～Ｃ６のハロアルキル基を表す。］で表される化合物（国際公開第１２／１６４６９８号参照）等が挙げられる。 [C-28.142] Equation (s59)
Figure JPOXMLDOC01-appb-C000139
[A90 represents a halogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group, A91 represents a C1-C6 haloalkyl group, A92 and A93 each independently represent a hydrogen atom, Represents a C1-C6 alkyl group, an acetyl group, a propionoyl group, a methanesulfonylethyl group, a methoxycarbonyl group, or an ethoxycarbonyl group, and A94 and A95 are each independently a hydrogen atom, a C1-C6 alkyl group, Or a C1-C6 haloalkyl group. And the like (see WO 12/1664698).
　本発明化合物と前述の必要に応じて混合して使用することができる他の農薬との混合比は、効果が発揮される限りにおいて特に制限されるものではないが、通常、本発明化合物に対して他の農薬は、重量比で０．００１～１０００の比率であり、好ましくは、０．０１～１００の比率である。 The mixing ratio of the compound of the present invention and other agrochemicals that can be used by mixing as necessary as described above is not particularly limited as long as the effect is exerted. Other pesticides have a weight ratio of 0.001 to 1000, preferably 0.01 to 100.
　以下に、合成例、参考例、および試験例を挙げて、本発明を更に詳細に示すが、本発明はこれらに限定されるものではない。 本 Hereinafter, the present invention will be described in more detail with reference to Synthesis Examples, Reference Examples, and Test Examples, but the present invention is not limited thereto.
［合成例１］
　ステップ１：６－（４－フルオロフェニル）－５－（チオフェン－３－イル）－３，４－ジヒドロピリジン－２（１Ｈ）－オンの合成
Figure JPOXMLDOC01-appb-C000140
 [Synthesis Example 1]
Step 1: Synthesis of 6- (4-fluorophenyl) -5- (thiophen-3-yl) -3,4-dihydropyridin-2 (1H) -one
Figure JPOXMLDOC01-appb-C000140
　参考例３で得られた５－（４－フルオロフェニル）－５－オキソ－４－（チオフェン－３－イル）－ペンタン酸　６．８１ｇと酢酸アンモニウム　６５．００ｇを含む酢酸溶液　２０ｍｌを、１２０℃にて６時間撹拌した。室温まで冷却した後に、反応混合物に酢酸エチルと水を加えて分液した。得られた有機層に水を加え、さらに発砲がおさまるまで飽和炭酸水素ナトリウム水溶液を加えた後に分液した。次いで、有機層を飽和食塩水にて洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去を行った後に、ジイソプロピルエーテルにより析出物を洗浄した。得られた褐色固体は表題の化合物であり、３．６１ｇであった。 20 ml of an acetic acid solution containing 6.81 g of 5- (4-fluorophenyl) -5-oxo-4- (thiophen-3-yl) -pentanoic acid obtained in Reference Example 3 and 65.00 g of ammonium acetate was added at 120 ° C. For 6 hours. After cooling to room temperature, ethyl acetate and water were added to the reaction mixture for liquid separation. Water was added to the obtained organic layer, and a saturated aqueous solution of sodium hydrogencarbonate was further added until the firing was stopped, followed by liquid separation. Next, the organic layer was washed with saturated saline and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the precipitate was washed with diisopropyl ether. The obtained brown solid was the title compound and weighed 3.61 g.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　７．２３－７．２１　（２Ｈ，　ｍ），　７．０８　（１Ｈ，　ｄｄ，　Ｊ　＝　５．１，　２．９　Ｈｚ），　７．０３－７．００　（２Ｈ，　ｍ），　６．８２　（１Ｈ，　ｄｄ，　Ｊ　＝　２．９，　１．２　Ｈｚ），　６．７９　（１Ｈ，　ｂｒ　ｓ），　６．５１　（１Ｈ，　ｄｄ，　Ｊ　＝　５．１，　１．２　Ｈｚ），　２．８９－２．８４　（２Ｈ，　ｍ），　２．７１－２．６７　（２Ｈ，　ｍ）． 1 H-NMR (CDCl 3 ) δ: 7.23-7.21 (2H, m), 7.08 (1H, dd, J = 5.1, 2.9 Hz), 7.03-7.00 (2H, m), 6.82 (1H, dd, J = 2.9, 1.2 Hz), 6.79 (1H, brs), 6.51 (1H, dd, J = 5.1, 1.2 Hz), 2.89-2.84 (2H, m), 2.71-2.67 (2H, m).
　ステップ２：１－エチル－６－（４－フルオロフェニル）－５－（チオフェン－３－イル）－３，４－ジヒドロピリジン－２（１Ｈ）－オンの合成
Figure JPOXMLDOC01-appb-C000141
 Step 2: Synthesis of 1-ethyl-6- (4-fluorophenyl) -5- (thiophen-3-yl) -3,4-dihydropyridin-2 (1H) -one
Figure JPOXMLDOC01-appb-C000141
　６－（４－フルオロフェニル）－５－（チオフェン－３－イル）－３，４－ジヒドロピリジン－２（１Ｈ）－オン　１．５０ｇ、ヨウ化エチル　２．６５ｍｌと炭酸セシウム４．４７ｇを含むＤＭＦ　３０ｍｌを７０℃で３時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層をチオ硫酸ナトリウム水溶液と飽和食塩水で順次洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が１．３６ｇの褐色固体として得られた。
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　７．１６－７．１５　（２Ｈ，　ｍ），　７．０５－７．０３　（３Ｈ，　ｍ），　６．５９　（１Ｈ，　ｄｄ，　Ｊ　＝　３．１，　１．３　Ｈｚ），　６．３９　（１Ｈ，　ｄｄ，　Ｊ　＝　５．１，　１．３　Ｈｚ），　３．４２　（２Ｈ，　ｑ，　Ｊ　＝　７．１　Ｈｚ），　２．７８－２．６５　（５Ｈ，　ｍ），　０．９３　（３Ｈ，　ｔ，　Ｊ　＝　７．１　Ｈｚ）． DMF containing 1.50 g of 6- (4-fluorophenyl) -5- (thiophen-3-yl) -3,4-dihydropyridin-2 (1H) -one, 2.65 ml of ethyl iodide and 4.47 g of cesium carbonate 30 ml was stirred at 70 ° C. for 3 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was sequentially washed with an aqueous solution of sodium thiosulfate and a saturated saline solution, and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 1.36 g of a brown solid.
1 H-NMR (CDCl 3 ) δ: 7.16-7.15 (2H, m), 7.05-7.03 (3H, m), 6.59 (1H, dd, J = 3.1, 1.3 Hz), 6.39 (1H, dd, J = 5.1, 1.3 Hz), 3.42 (2H, q, J = 7.1 Hz), 2.78-2.65 (2,78-2.65) 5H, m), 0.93 (3H, t, J = 7.1 Hz).
　ステップ３：５－（２－ブロモチオフェン－３－イル）－１－エチル－６－（４－フルオロフェニル）－３，４－ジヒドロピリジン－２（１Ｈ）－オンの合成（化合物番号：４）
Figure JPOXMLDOC01-appb-C000142
 Step 3: Synthesis of 5- (2-bromothiophen-3-yl) -1-ethyl-6- (4-fluorophenyl) -3,4-dihydropyridin-2 (1H) -one (Compound No .: 4)
Figure JPOXMLDOC01-appb-C000142
　１－エチル－６－（４－フルオロフェニル）－５－（チオフェン－３－イル）－３，４－ジヒドロピリジン－２（１Ｈ）－オン　６３７ｍｇとＮ－ブロモスクシンイミド　４１４ｍｇを含む四塩化炭素溶液　１０ｍｌを６０℃で１時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層をチオ硫酸ナトリウム水溶液と飽和食塩水で順次洗浄して、硫酸ナトリウムで乾燥した。減圧下で溶媒留去をした後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が６９４ｍｇの褐色固体として得られた。 10 ml of a carbon tetrachloride solution containing 637 mg of 1-ethyl-6- (4-fluorophenyl) -5- (thiophen-3-yl) -3,4-dihydropyridin-2 (1H) -one and 414 mg of N-bromosuccinimide Stirred at 60 ° C. for 1 hour. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was sequentially washed with an aqueous solution of sodium thiosulfate and a saturated saline solution, and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 694 mg of a brown solid.
［合成例２］
　５－（２－ブロモチオフェン－３－イル）－１－エチル－６－（４－フルオロフェニル）ピリジン－２（１Ｈ）－オンの合成（化合物番号：５）
Figure JPOXMLDOC01-appb-C000143
 [Synthesis Example 2]
Synthesis of 5- (2-bromothiophen-3-yl) -1-ethyl-6- (4-fluorophenyl) pyridin-2 (1H) -one (Compound No .: 5)
Figure JPOXMLDOC01-appb-C000143
　５－（２－ブロモチオフェン－３－イル）－１－エチル－６－（４－フルオロフェニル）－３，４－ジヒドロピリジン－２（１Ｈ）－オン　６２９ｍｇを含む四塩化炭素溶液　１２ｍｌに、Ｎ－ブロモスクシンイミド　２９５ｍｇとアゾビスイソブチロニトリル　２７ｍｇを加えて、７０℃で３時間撹拌した。室温まで冷却した後に、反応混合物にジクロロメタンとチオ硫酸ナトリウム水溶液を加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下にて溶媒留去した後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。表題の化合物が４９３ｍｇの白色固体として得られた。 To 12 ml of a carbon tetrachloride solution containing 629 mg of 5- (2-bromothiophen-3-yl) -1-ethyl-6- (4-fluorophenyl) -3,4-dihydropyridin-2 (1H) -one was added N- Bromosuccinimide (295 mg) and azobisisobutyronitrile (27 mg) were added, and the mixture was stirred at 70 ° C. for 3 hours. After cooling to room temperature, dichloromethane and an aqueous solution of sodium thiosulfate were added to the reaction mixture to carry out liquid separation. The obtained organic layer was washed with a saturated saline solution and dried with sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 493 mg of a white solid.
［合成例３］
　５－（２－ブロモチオフェン－３－イル）－３－クロロ－１－エチル－６－（４－フルオロフェニル）ピリジン－２（１Ｈ）－オンの合成（化合物番号：７）
Figure JPOXMLDOC01-appb-C000144
 [Synthesis Example 3]
Synthesis of 5- (2-bromothiophen-3-yl) -3-chloro-1-ethyl-6- (4-fluorophenyl) pyridin-2 (1H) -one (Compound No .: 7)
Figure JPOXMLDOC01-appb-C000144
　５－（２－ブロモチオフェン－３－イル）－１－エチル－６－（４－フルオロフェニル）ピリジン－２（１Ｈ）－オン　２５０ｍｇとＮ－クロロスクシンイミド　９７ｍｇを含むＤＭＦ溶液　５ｍｌを７０℃で４時間撹拌した。室温まで冷却した後に、反応混合物に水と酢酸エチルを加えて分液した。得られた有機層をチオ硫酸ナトリウム水溶液と飽和食塩水で順次洗浄して、硫酸ナトリウムで乾燥した。減圧下で溶媒留去をした後に、得られた残渣をシリカゲルカラムクロマトグラフィーにて精製した。減圧下で溶媒留去を行った後に、ジイソプロピルエーテルにより析出物を洗浄した。得られた白色固体は表題の化合物であり、２４６ｍｇであった。 5 ml of a DMF solution containing 250 mg of 5- (2-bromothiophen-3-yl) -1-ethyl-6- (4-fluorophenyl) pyridin-2 (1H) -one and 97 mg of N-chlorosuccinimide was added at 70 ° C. Stirred for hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was sequentially washed with an aqueous solution of sodium thiosulfate and a saturated saline solution, and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. After the solvent was distilled off under reduced pressure, the precipitate was washed with diisopropyl ether. The obtained white solid was the title compound and was 246 mg.
［参考例１］
　１－（４－フルオロフェニル）－２－（チオフェン－３－イル）エタン－１－オンの合成
Figure JPOXMLDOC01-appb-C000145
 [Reference Example 1]
Synthesis of 1- (4-fluorophenyl) -2- (thiophen-3-yl) ethan-1-one
Figure JPOXMLDOC01-appb-C000145
　２－（チオフェン－３－イル）酢酸　３．００ｇを含むＴＨＦ溶液　４０ｍｌに、１．９ｍｏｌ／ＬのヘキサメチルジシラザンナトリウムのＴＨＦ溶液　３５．５ｍｌを－７８℃で滴下して３０分間撹拌した。次いで、ｐ－フルオロ安息香酸メチル　２．７１ｍｌを滴下した後に、－７８℃から室温まで昇温して１５分間撹拌した。これに飽和塩化アンモニウム水溶液を加えて撹拌した後に、酢酸エチルを加えて分液した。得られた有機層を飽和食塩水で洗浄し、硫酸ナトリウムで乾燥した。減圧下で溶媒留去した後に、標題の化合物を含む５．４２ｇの黄色固体を得た。これ以上精製することなく、次の反応に使用した。 To a 40 ml THF solution containing 3.00 g of {2- (thiophen-3-yl) acetic acid} was added dropwise 35.5 ml of a 1.9 mol / L THF solution of sodium hexamethyldisilazane at −78 ° C., followed by stirring for 30 minutes. Then, 2.71 ml of methyl p-fluorobenzoate was added dropwise, and the mixture was heated from -78 ° C to room temperature and stirred for 15 minutes. A saturated aqueous ammonium chloride solution was added thereto, and the mixture was stirred. Ethyl acetate was added, and the mixture was separated. The obtained organic layer was washed with a saturated saline solution and dried with sodium sulfate. After evaporating the solvent under reduced pressure, 5.42 g of a yellow solid containing the title compound was obtained. Used for the next reaction without further purification.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　８．０５－８．０２　（２Ｈ，　ｍ），　７．３１　（１Ｈ，　ｄｄ，　Ｊ　＝　４．９，　３．１　Ｈｚ），　７．１５－７．１２　（３Ｈ，　ｍ），　７．０１　（１Ｈ，　ｄｄ，　Ｊ　＝　４．９，　１．２　Ｈｚ），　４．２８　（２Ｈ，　ｓ）． 1 H-NMR (CDCl 3 ) δ: 8.05-8.02 (2H, m), 7.31 (1H, dd, J = 4.9, 3.1 Hz), 7.15-7.12 (3H, m), 7.01 (1H, dd, J = 4.9, 1.2 Hz), 4.28 (2H, s).
［参考例２］
　５－（４－フルオロフェニル）－５－オキソ－４－（チオフェン－３－イル）ペンタン酸エチルの合成
Figure JPOXMLDOC01-appb-C000146
 [Reference Example 2]
Synthesis of ethyl 5- (4-fluorophenyl) -5-oxo-4- (thiophen-3-yl) pentanoate
Figure JPOXMLDOC01-appb-C000146
　参考例１で得られた１－（４－フルオロフェニル）－２－（チオフェン－３－イル）エタン－１－オン　５．４２ｇを含むＴＨＦ溶液　３０ｍｌに、カリウム　ｔ－ブトキシド　２３７ｍｇとアクリル酸エチル　２．３０ｍｌを加えて、室温下で３０分間撹拌した。これに飽和塩化アンモニウム溶液と酢酸エチルを加えて分液した後に、得られた有機層を飽和食塩水にて洗浄し、硫酸ナトリウムで乾燥した。減圧下にて溶媒留去した後に、表題の化合物を含む５．１８ｇの黄色油状物質を得た。これ以上精製することなく、次の反応に使用した。 In a THF solution (30 ml) containing 1- (4-fluorophenyl) -2- (thiophen-3-yl) ethan-1-one (5.42 g) obtained in Reference Example 1, potassium (t-butoxide) (237 mg) and ethyl acrylate (2) were added. After adding 30 ml, the mixture was stirred at room temperature for 30 minutes. After a saturated ammonium chloride solution and ethyl acetate were added thereto and the mixture was separated, the obtained organic layer was washed with saturated saline and dried over sodium sulfate. After evaporating the solvent under reduced pressure, 5.18 g of a yellow oily substance containing the title compound was obtained. Used for the next reaction without further purification.
１Ｈ－ＮＭＲ　（ＣＤＣｌ３）　δ：　８．００　（２Ｈ，　ｄｄｄ，　Ｊ　＝　７．１，　５．１，　１．８　Ｈｚ），　７．２７　（１Ｈ，　ｄｄ，　Ｊ　＝　４．９，　３．１　Ｈｚ），　７．１１－７．０６　（３Ｈ，　ｍ），　７．０１　（１Ｈ，　ｄｄ，　Ｊ　＝　４．９，　１．２　Ｈｚ），　４．８２　（１Ｈ，　ｔ，　Ｊ　＝　７．３　Ｈｚ），　４．１２　（２Ｈ，　ｔｄ，　Ｊ　＝　８．８，　２．８　Ｈｚ），　２．３９　（１Ｈ，　ｄｄｄ，　Ｊ　＝　１４．０，　７．３，　５．９　Ｈｚ），　２．３１－２．２８　（２Ｈ，　ｍ），　２．１９－２．１４　（１Ｈ，　ｍ），　１．２５－１．２０　（３Ｈ，　ｍ）． 1 H-NMR (CDCl 3 ) δ: 8.00 (2H, ddd, J = 7.1, 5.1, 1.8 Hz), 7.27 (1H, dd, J = 4.9, 3. 1 Hz), 7.11-7.06 (3H, m), 7.01 (1H, dd, J = 4.9, 1.2 Hz), 4.82 (1H, t, J = 7.3). Hz), 4.12 (2H, td, J = 8.8, 2.8 Hz), 2.39 (1H, ddd, J = 14.0, 7.3, 5.9 Hz), 2.31 -2.28 (2H, m), 2.19-2.14 (1H, m), 1.25-1.20 (3H, m).
［参考例３］
　５－（４－フルオロフェニル）－５－オキソ－４－（チオフェン－３－イル）－ペンタン酸の合成
Figure JPOXMLDOC01-appb-C000147
 [Reference Example 3]
Synthesis of 5- (4-fluorophenyl) -5-oxo-4- (thiophen-3-yl) -pentanoic acid
Figure JPOXMLDOC01-appb-C000147
　参考例２で得られた５－（４－フルオロフェニル）－５－オキソ－４－（チオフェン－３－イル）ペンタン酸エチル　５．１８ｇを含む酢酸　２０ｍｌに、濃塩酸　１０ｍｌを加えて、１００℃で３時間撹拌した。室温まで冷却した後に、水と酢酸エチルを加えて分液した。得られた有機層を飽和食塩水にて洗浄し、硫酸ナトリウムで乾燥した。次いで、減圧下にて溶媒留去した後に、表題の化合物を含む６．８１ｇの黄色油状物質を得た。これ以上精製することなく、次の反応に使用した。 10 ml of concentrated hydrochloric acid was added to 20 ml of acetic acid containing 5.18 g of ethyl 5- (4-fluorophenyl) -5-oxo-4- (thiophen-3-yl) pentanoate obtained in Reference Example 2, and 100 ° C. For 3 hours. After cooling to room temperature, water and ethyl acetate were added to carry out liquid separation. The obtained organic layer was washed with a saturated saline solution and dried with sodium sulfate. Then, after evaporating the solvent under reduced pressure, 6.81 g of a yellow oily substance containing the title compound was obtained. Used for the next reaction without further purification.
　表４に、前記した実施例に準じて合成した化合物を示すが、本発明はこれらに限定されるものではない。 Table 4 shows compounds synthesized according to the above-mentioned Examples, but the present invention is not limited to these.
　表４中、構造Ａは以下を示す。 構造 In Table 4, Structure A shows the following.
Figure JPOXMLDOC01-appb-C000148
Figure JPOXMLDOC01-appb-C000148
　表４中、構造Ｂは以下を示す。 構造 In Table 4, Structure B shows the following.
Figure JPOXMLDOC01-appb-C000149
Figure JPOXMLDOC01-appb-C000149
　表４中、構造Ｃは以下を示す。 構造 In Table 4, Structure C shows the following.
Figure JPOXMLDOC01-appb-C000150
Figure JPOXMLDOC01-appb-C000150
　表４中、構造Ｄは以下を示す。 中 In Table 4, Structure D shows the following.
Figure JPOXMLDOC01-appb-C000151
Figure JPOXMLDOC01-appb-C000151
Figure JPOXMLDOC01-appb-T000152
Figure JPOXMLDOC01-appb-T000152
　次に、表４に記載の化合物に関して、表５にそれらの１Ｈ－ＮＭＲデータを示す。 Next, regarding the compounds described in Table 4, Table 1 shows their 1 H-NMR data.
Figure JPOXMLDOC01-appb-T000153
Figure JPOXMLDOC01-appb-T000153
　次に、本発明化合物が植物病害に有効であることを具体的に示すが、これらの例に限定されるものではない。 Next, the compounds of the present invention are specifically shown to be effective against plant diseases, but are not limited to these examples.
［試験例Ａ］　イネいもち病
　供試植物（イネ品種：幸風）の種子を播種後、第２葉が展開するまで栽培した。試験では、本発明化合物をジメチルスルホキシド－メタノール混合溶液（容積比：９／１）に溶解し、２５０ｐｐｍの濃度となるように井戸水で希釈して薬液を得た。得られた薬液を供試植物に散布した（２．５ｍｌ／ポット）。薬液が乾燥した後の植物に、１～２×１０５個／ｍｌのイネいもち病菌（Ｍａｇｎａｐｏｒｔｈｅ　ｇｒｉｓｅａ）の分生胞子懸濁液を噴霧接種した。接種後、室温が２０～２３℃の湿室に約２４時間放置し、発病を促した。接種６～１０日後の発病程度を調査し、薬液の効果を評価した。 [Test Example A] Rice blast A seed of a test plant (rice cultivar: Kofu) was sown, and then cultivated until the second leaf developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the chemical solution was dried, the plants were spray-inoculated with a conidia suspension of 1-2 × 10 5 cells / ml of rice blast fungus (Magnaporthe grisea). After the inoculation, the cells were allowed to stand in a wet room at room temperature of 20 to 23 ° C. for about 24 hours to promote the onset of the disease. The onset of disease 6 to 10 days after inoculation was investigated, and the effect of the drug solution was evaluated.
［試験例Ｂ］　トマト灰色かび病
　供試植物（トマト品種：大型福寿）の種子を播種後、本葉が３～５枚展開するまで栽培した。試験では、本発明化合物をジメチルスルホキシド－メタノール混合溶液（容積比：９／１）に溶解し、２５０ｐｐｍの濃度となるように井戸水で希釈して薬液を得た。得られた薬液を供試植物に散布した（２．５ｍｌ／ポット）。薬液が乾燥した後の植物に、４～８×１０５個／ｍｌの灰色かび病菌（Ｂｏｔｒｙｔｉｓ　ｃｉｎｅｒｅａ）の分生胞子懸濁液を噴霧接種した。接種後、室温が２０～２３℃の湿室に約４８時間放置し、発病を促した。接種２～３日後の発病程度を調査し、薬液の効果を評価した。 [Test Example B] Tomato gray mold A seed of a test plant (tomato variety: large fukuju) was sown, and then cultivated until 3 to 5 true leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the chemical solution was dried, the plants were spray-inoculated with a conidia suspension of Botrytis cinerea at 4 to 8 × 10 5 cells / ml. After the inoculation, the cells were allowed to stand in a wet room at room temperature of 20 to 23 ° C. for about 48 hours to promote the onset of the disease. The onset of disease 2-3 days after inoculation was investigated, and the effect of the drug solution was evaluated.
［試験例Ｃ］　キャベツ黒すす病
　供試植物（キャベツ品種：四季穫）の種子を播種後、子葉が展開するまで栽培した。試験では、本発明化合物をジメチルスルホキシド－メタノール混合溶液（容積比：９／１）に溶解し、２５０ｐｐｍの濃度となるように井戸水で希釈して薬液を得た。得られた薬液を供試植物に散布した（２．５ｍｌ／ポット）。薬液が乾燥した後の植物に、４～８×１０５個／ｍｌのキャベツ黒すす病菌（Ａｌｔｅｒｎａｉａ　ｂｒａｓｓｉｃｉｃｏｌａ）の分生胞子懸濁液を噴霧接種した。接種後、室温が２０～２３℃の湿室に約４８時間放置し、発病を促した。接種２～３日後の発病程度を調査し、薬液の効果を評価した。 [Test Example C] Cabbage black spot disease Seeds of a test plant (cabbage variety: four seasons harvest) were sown and then cultivated until cotyledons developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the chemical solution was dried, the plants were spray-inoculated with a conidia suspension of 4-8 × 10 5 cells / ml of cabbage black rot fungus (Alternia brassicicola). After the inoculation, the cells were allowed to stand in a wet room at room temperature of 20 to 23 ° C. for about 48 hours to promote the onset of the disease. The onset of disease 2-3 days after inoculation was investigated, and the effect of the drug solution was evaluated.
［試験例Ｄ］　オオムギうどんこ病
　供試植物（オオムギ品種：赤神力）の種子を播種後、第１葉が展開するまで栽培した。試験では、本発明化合物をジメチルスルホキシド－メタノール混合溶液（容積比：９／１）に溶解し、２５０ｐｐｍの濃度となるように井戸水で希釈して薬液を得た。得られた薬液を供試植物に散布した（２．５ｍｌ／ポット）。薬液が乾燥した後の植物に、オオムギうどんこ病菌（Ｂｌｕｍｅｒｉａ　ｇｒａｍｉｎｉｓ　ｆ．ｓｐ．ｈｏｒｄｅｉ）の分生胞子を叩き落して接種した。接種後、６～１０日後の発病程度を調査し、その効果を評価した。 [Test Example D] Barley powdery mildew Seeds of a test plant (barley variety: Akagami Riki) were sown and then cultivated until the first leaves were developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the chemical solution was dried, the conidia of barley powdery mildew (Blumeria graminis f.sp.hordei) were beaten and inoculated to the plants. 6 to 10 days after the inoculation, the degree of onset was investigated, and the effect was evaluated.
［試験例Ｅ］　コムギ赤さび病
　供試植物（コムギ品種：農林６１号）の種子を播種後、第１葉が展開するまで栽培した。試験では、本発明化合物をジメチルスルホキシド－メタノール混合溶液（容積比：９／１）に溶解し、２５０ｐｐｍの濃度となるように井戸水で希釈して薬液を得た。得られた薬液を供試植物に散布した（２．５ｍｌ／ポット）。薬液が乾燥した後の植物に、１～２×１０５個／ｍｌのコムギ赤さび病菌（Ｐｕｃｃｉｎｉａ　ｒｅｃｏｎｄｉｔａ）の夏胞子懸濁液を噴霧接種した。接種後、室温が２０～２３℃の湿室に約２４時間放置し、発病を促した。接種７～１０日後の発病程度を調査し、薬液の効果を評価した。 [Test Example E] Wheat leaf rust Seeds of a test plant (wheat variety: Norin 61) were sown and then cultivated until the first leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the medicinal solution was dried, the plants were spray-inoculated with a uredospore suspension of 1-2 × 10 5 cells / ml of wheat leaf rust (Puccinia recondita). After the inoculation, the cells were allowed to stand in a wet room at room temperature of 20 to 23 ° C. for about 24 hours to promote the onset of the disease. The onset of disease 7 to 10 days after inoculation was investigated, and the effect of the drug solution was evaluated.
［試験例Ｆ］　トマト疫病
　供試植物（トマト品種：大型福寿）の種子を播種後、本葉が３～５枚展開するまで栽培した。試験では、本発明化合物をジメチルスルホキシド－メタノール混合溶液（容積比：９／１）に溶解し、２５０ｐｐｍの濃度となるように井戸水で希釈して薬液を得た。得られた薬液を供試植物に散布した（２．５ｍｌ／ポット）。薬液が乾燥した後の植物に、４～８×１０３個／ｍｌのトマト疫病菌（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｉｎｆｅｓｔａｎｓ）の遊走子のう懸濁液を噴霧接種した。接種後、室温が２０℃の湿室に約２４時間放置し、発病を促した。接種５～１０日後の発病程度を調査し、薬液の効果を評価した。 [Test Example F] Tomato late blight Seeds of a test plant (tomato variety: large fukuju) were sown, and then cultivated until three to five true leaves were developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the chemical solution was dried, the plants were spray-inoculated with a zoospore suspension of 4 to 8 × 10 3 cells / ml of Phytophthora infestans. After the inoculation, the cells were left in a wet room at room temperature of 20 ° C. for about 24 hours to promote the onset of the disease. The disease onset 5 to 10 days after the inoculation was investigated, and the effect of the drug solution was evaluated.
［試験例Ｇ］　ブドウべと病
　供試植物（ブドウ品種：ネオマスカット）の種子を播種後、本葉が３～４枚展開するまで栽培した。試験では、本発明化合物をジメチルスルホキシド－メタノール混合溶液（容積比：９／１）に溶解し、２５０ｐｐｍの濃度となるように井戸水で希釈して薬液を得た。得られた薬液を供試植物に散布した（２．５ｍｌ／ポット）。薬液が乾燥した後の植物に、１～２×１０４個／ｍｌのブドウべと病菌（Ｐｌａｓｍｏｐａｒａ　ｖｉｔｉｃｏｌａ）の遊走子のう懸濁液を噴霧接種した。接種後、室温が２０℃の湿室に約２４時間放置し、発病を促した。接種７～１０日後の発病程度を調査し、薬液の効果を評価した。 [Test Example G] Grape downy mildew Seeds of a test plant (grape variety: Neo Muscat) were sown, and then cultivated until three to four true leaves were developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the medicinal solution was dried, the plants were spray-inoculated with a zoospore suspension of Plasmopara viticola at 1-2 × 10 4 cells / ml. After the inoculation, the cells were left in a wet room at room temperature of 20 ° C. for about 24 hours to promote the onset of the disease. The onset of disease 7 to 10 days after inoculation was investigated, and the effect of the drug solution was evaluated.
［試験例Ｈ］　キュウリ炭疽病
　供試植物（キュウリ品種：相模半白）の種子を播種後、本葉が１枚展開するまで栽培した。試験では、本発明化合物をジメチルスルホキシド－メタノール混合溶液（容積比：９／１）に溶解し、２５０ｐｐｍの濃度となるように井戸水で希釈して薬液を得た。得られた薬液を供試植物に散布した（２．５ｍｌ／ポット）。薬液が乾燥した後の植物に、２～４×１０５個／ｍｌのキュウリ炭疽病菌（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｏｒｂｉｃｕｌａｒｅ）の分生胞子懸濁液を噴霧接種した。接種後、室温が２０～２３℃の湿室に約２４時間放置し、発病を促した。接種６～１０日後の発病程度を調査し、薬液の効果を評価した。 [Test Example H] Cucumber Anthrax Disease Seeds of a test plant (cucumber variety: Sagami Hanjiro) were sown, and then cultivated until one true leaf developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1), and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plant (2.5 ml / pot). After the medicinal solution was dried, the plants were spray-inoculated with a conidia spore suspension of 2 to 4 × 10 5 cells / ml of cucumber anthrax (Colletotrichum orbiculare). After the inoculation, the cells were allowed to stand in a wet room at room temperature of 20 to 23 ° C. for about 24 hours to promote the onset of the disease. The onset of disease 6 to 10 days after inoculation was investigated, and the effect of the drug solution was evaluated.
　以上に示した試験例の発病程度について、無発病の植物の発病程度を０、薬剤無処理区の植物の発病程度を３として、０．０５ごとの発病程度の評価を行った。また、発病程度から以下の計算式に従って防除価を算出した。 With respect to the degree of disease in the test examples described above, the degree of disease was evaluated for each 0.05, with the degree of disease occurring in uninfected plants being 0 and the degree of disease occurring in plants in the non-treated area being set to 3. Further, the control value was calculated from the degree of onset according to the following formula.
＜防除価＞
　防除価＝１００｛１－（ｎ／３）｝
　ｎ＝各薬剤処理区の発病程度
以上の試験結果をまとめたものを表６に示す。表中、Ｈは防除価が５０％より大きいもの表し、Ｌは防除価が５０％以下を表す。また、ｎｔは試験を実施しなかったことを表す。 <Control value>
Control value = 100 {1- (n / 3)}
Table 6 shows a summary of the test results of n = disease level or higher in each drug treatment section. In the table, H indicates that the control value is greater than 50%, and L indicates that the control value is 50% or less. In addition, nt indicates that the test was not performed.
Figure JPOXMLDOC01-appb-T000154
Figure JPOXMLDOC01-appb-T000154
　本発明化合物は新規な化合物であり、植物病害を防除することができるので、農薬、例えば、農園芸用有害生物防除剤、特に農園芸用殺菌剤としての利用価値がある。 化合物 The compound of the present invention is a novel compound and can control plant diseases, and therefore has a value as a pesticide, for example, a pesticide for agricultural and horticultural use, particularly a fungicide for agricultural and horticultural use.

Claims (8)

  1. 　式（１）
    Figure JPOXMLDOC01-appb-C000001
    　［式中、Ｒ１は、
    　　水酸基、
    　　シアノ基、
    　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　　Ｃ１～Ｃ６のハロアルキル基、
    　　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　　Ｃ２～Ｃ６のハロアルケニル基、
    　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　　Ｃ２～Ｃ６のハロアルキニル基、
    　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　　Ｃ１～Ｃ６のハロアルコキシ基、
    　　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
    　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
    　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
    　　置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
    　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
    　　またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表し；
    　Ｒ２、Ｒ３およびＲ４は、それぞれ独立していて、
    　　水素原子、
    　　ハロゲン原子、
    　　水酸基、
    　　シアノ基、
    　　ニトロ基、
    　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　　Ｃ１～Ｃ６のハロアルキル基、
    　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　　Ｃ２～Ｃ６のハロアルケニル基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　　Ｃ２～Ｃ６のハロアルキニル基、
    　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　　Ｃ１～Ｃ６のハロアルコキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
    　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
    　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
    　　置換基Ｄで適宜０～５置換されてもよいアリールオキシ基、
    　　置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基、
    　　置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、
    　　Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表す。）、
    　　Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、前記と同義である。）、
    　　１～２個の酸素原子を含む３～６員環の基、
    　　Ｒｃ－Ｌ－（ここで、Ｒｃは、Ｃ１～Ｃ６のアルキル基またはＣ１～Ｃ６のハロアルキル基を表し、Ｌは、Ｓ、ＳＯ、またはＳＯ２を表す。）、
    　　ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
    　　またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表し、Ｒｘ３は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。）を表し；
    　Ｒ５は、
    　　水素原子、
    　　ハロゲン原子、
    　　シアノ基、
    　　ニトロ基、
    　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　　Ｃ１～Ｃ６のハロアルキル基、
    　　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　　Ｃ２～Ｃ６のハロアルケニル基、
    　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　　Ｃ２～Ｃ６のハロアルキニル基、
    　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　　Ｃ１～Ｃ６のハロアルコキシ基、
    　　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
    　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
    　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
    　　置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
    　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
    　　Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
    　　ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
    　　またはＲ５１Ｃ（＝Ｏ）－（ここで、Ｒ５１は、水酸基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、またはＣ１～Ｃ６のアルコキシ基を表す。）を表し；
    　Ｘは、酸素原子または硫黄原子を表し；
    　Ｙは、式（ｙ－１）、または式（ｙ－２）
    Figure JPOXMLDOC01-appb-C000002
    を表し、
    　Ｒ６は、
    　　ハロゲン原子、
    　　水酸基、
    　　シアノ基、
    　　ニトロ基、
    　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　　Ｃ１～Ｃ６のハロアルキル基、
    　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　　Ｃ２～Ｃ６のハロアルケニル基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　　Ｃ２～Ｃ６のハロアルキニル基、
    　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　　Ｃ１～Ｃ６のハロアルコキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
    　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
    　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
    　　置換基Ｄで適宜０～５置換されてもよいアリールオキシ基、
    　　置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基、
    　　置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、
    　　Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、前記と同義である。）、
    　　Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、前記と同義である。）、
    　　１～２個の酸素原子を含む３～６員環の基、
    　　Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
    　　ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
    　　またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２およびＲｘ３は、前記と同義である。）を表し；
    　ｎは、０～３の整数（ｎが２以上の場合、２以上のＲ６はそれぞれ独立した置換基を表す。）を表し；
    　破線部を含む結合は、二重結合、または単結合を表し；
    　そして、置換基Ａは、水酸基、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）およびＲｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）からなる群から選択される少なくとも１種であり；
    　置換基Ｂは、シアノ基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種であり；
    　置換基Ｃは、水酸基、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、Ｃ２～Ｃ６のアルコキシアルコキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、ＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記のＲｘ１と同義である。）および１～２個の酸素原子を含む３～６員環の基からなる群から選択される少なくとも１種であり；
    　置換基Ｄは、ハロゲン原子、水酸基、シアノ基、ニトロ基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種である。］で表される化合物、またはその塩。     Equation (1)
    Figure JPOXMLDOC01-appb-C000001
    Wherein R1 is
    Hydroxyl group,
    Cyano group,
    A C1-C6 alkyl group optionally substituted with a substituent A,
    A C1-C6 haloalkyl group,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A,
    A C2-C6 alkenyl group optionally substituted with a substituent A,
    A C2-C6 haloalkenyl group,
    A C2-C6 alkynyl group optionally substituted with a substituent A,
    A C2-C6 haloalkynyl group,
    A C1-C6 alkoxy group optionally substituted with a substituent A,
    C1-C6 haloalkoxy groups,
    A C3-C8 cycloalkoxy group optionally substituted with a substituent A,
    A C2-C6 alkenyloxy group optionally substituted with a substituent A,
    A C2-C6 haloalkenyloxy group,
    A C3-C6 alkynyloxy group optionally substituted with a substituent A,
    A C3-C6 haloalkynyloxy group,
    Or RaRbN- (where Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 Represents a cycloalkyl group, or Ra and Rb represent, together with the nitrogen atom to be bound, an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group. Represent;
    R2, R3 and R4 are each independently;
    Hydrogen atom,
    Halogen atom,
    Hydroxyl group,
    Cyano group,
    Nitro group,
    A C1-C6 alkyl group optionally substituted with a substituent C,
    A C1-C6 haloalkyl group,
    A C3-C8 cycloalkyl group optionally substituted with a substituent C,
    A C2-C6 alkenyl group optionally substituted with a substituent C,
    A C2-C6 haloalkenyl group,
    A C2-C6 alkynyl group optionally substituted with a substituent C,
    A C2-C6 haloalkynyl group,
    A C1-C6 alkoxy group optionally substituted with a substituent C,
    C1-C6 haloalkoxy groups,
    A C3-C8 cycloalkoxy group optionally substituted with a substituent C,
    A C2-C6 alkenyloxy group optionally substituted with a substituent C,
    A C2-C6 haloalkenyloxy group,
    A C3-C6 alkynyloxy group optionally substituted with a substituent C,
    A C3-C6 haloalkynyloxy group,
    An aryloxy group optionally substituted with 0 to 5 substituents D,
    A heteroaryloxy group optionally substituted with 0 to 2 substituents D,
    An aralkyloxy group optionally substituted with 0 to 5 substituents D,
    Rx1C (= O)-(where Rx1 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group which may be appropriately substituted with a substituent B A group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb have the same meanings as described above),
    Rx1C (= O) O- (where Rx1 is as defined above),
    A 3-6 membered ring group containing 1-2 oxygen atoms,
    Rc-L-(wherein, Rc represents a haloalkyl group of alkyl or C1 ~ C6 of C1 ~ C6, L represents S, SO, or SO 2.),
    RaRbN- (where Ra and Rb are as defined above),
    Or Rx2C (= O) N (Rx3)-(where Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl Represents an alkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN— (where Ra and Rb have the same meanings as described above), and Rx3 represents , A hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be optionally substituted with a substituent B);
    R5 is
    Hydrogen atom,
    Halogen atom,
    Cyano group,
    Nitro group,
    A C1-C6 alkyl group optionally substituted with a substituent A,
    A C1-C6 haloalkyl group,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A,
    A C2-C6 alkenyl group optionally substituted with a substituent A,
    A C2-C6 haloalkenyl group,
    A C2-C6 alkynyl group optionally substituted with a substituent A,
    A C2-C6 haloalkynyl group,
    A C1-C6 alkoxy group optionally substituted with a substituent A,
    C1-C6 haloalkoxy groups,
    A C3-C8 cycloalkoxy group optionally substituted with a substituent A,
    A C2-C6 alkenyloxy group optionally substituted with a substituent A,
    A C2-C6 haloalkenyloxy group,
    A C3-C6 alkynyloxy group optionally substituted with a substituent A,
    A C3-C6 haloalkynyloxy group,
    Rc-L- (where Rc and L are as defined above),
    RaRbN- (where Ra and Rb are as defined above),
    Or R51C (＝ O)-(where R51 is a hydroxyl group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, or a C1 Represents an alkoxy group of -C6);
    X represents an oxygen atom or a sulfur atom;
    Y is the formula (y-1) or the formula (y-2)
    Figure JPOXMLDOC01-appb-C000002
    Represents
    R6 is
    Halogen atom,
    Hydroxyl group,
    Cyano group,
    Nitro group,
    A C1-C6 alkyl group optionally substituted with a substituent C,
    A C1-C6 haloalkyl group,
    A C3-C8 cycloalkyl group optionally substituted with a substituent C,
    A C2-C6 alkenyl group optionally substituted with a substituent C,
    A C2-C6 haloalkenyl group,
    A C2-C6 alkynyl group optionally substituted with a substituent C,
    A C2-C6 haloalkynyl group,
    A C1-C6 alkoxy group optionally substituted with a substituent C,
    C1-C6 haloalkoxy groups,
    A C3-C8 cycloalkoxy group optionally substituted with a substituent C,
    A C2-C6 alkenyloxy group optionally substituted with a substituent C,
    A C2-C6 haloalkenyloxy group,
    A C3-C6 alkynyloxy group optionally substituted with a substituent C,
    A C3-C6 haloalkynyloxy group,
    An aryloxy group optionally substituted with 0 to 5 substituents D,
    A heteroaryloxy group optionally substituted with 0 to 2 substituents D,
    An aralkyloxy group optionally substituted with 0 to 5 substituents D,
    Rx1C (= O)-(where Rx1 is as defined above),
    Rx1C (= O) O- (where Rx1 is as defined above),
    A 3-6 membered ring group containing 1-2 oxygen atoms,
    Rc-L- (where Rc and L are as defined above),
    RaRbN- (where Ra and Rb are as defined above),
    Or Rx2C (= O) N (Rx3)-(where Rx2 and Rx3 are as defined above);
    n represents an integer of 0 to 3 (when n is 2 or more, 2 or more R6 each represents an independent substituent);
    A bond containing a broken line represents a double bond or a single bond;
    The substituent A is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, RaRbN- (where Ra And Rb are as defined above, and Rc-L- (wherein Rc and L are as defined above), and are at least one selected from the group consisting of:
    Substituent B is at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group;
    Substituent C is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN -(Where Ra and Rb are as defined above), Rc-L- (where Rc and L are as defined above), RdC (= O)-(where Rd Is the same as defined above for Rx1), and is at least one member selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
    Substituent D is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C8 It is at least one selected from the group consisting of a C6 alkoxy group, a C1 to C6 haloalkoxy group and a C3 to C8 cycloalkoxy group. Or a salt thereof.
  2. 　Ｒ１は、
    　　シアノ基、
    　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　　Ｃ１～Ｃ６のハロアルキル基、
    　　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　　Ｃ２～Ｃ６のハロアルケニル基、
    　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　　またはＣ２～Ｃ６のハロアルキニル基を表し；
    　Ｒ２、Ｒ３およびＲ４は、それぞれ独立していて、
    　　水素原子、
    　　ハロゲン原子、
    　　水酸基、
    　　シアノ基、
    　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　　Ｃ１～Ｃ６のハロアルキル基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　　Ｃ１～Ｃ６のハロアルコキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
    　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
    　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
    　　置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、
    　　またはＲｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表す。）を表し；
    　Ｒ５は、
    　　水素原子、
    　　ハロゲン原子、
    　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　　Ｃ１～Ｃ６のハロアルキル基、
    　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
    　　置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
    　　またはＲ５１Ｃ（＝Ｏ）－（ここで、Ｒ５１は、水酸基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、またはＣ１～Ｃ６のアルコキシ基を表す。）を表し；
    　Ｒ６は、
    　　ハロゲン原子、
    　　水酸基、
    　　シアノ基、
    　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　　Ｃ１～Ｃ６のハロアルキル基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　　Ｃ１～Ｃ６のハロアルコキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
    　　Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、前記と同義である。）、
    　　Ｒｃ－Ｌ－（ここで、Ｒｃは、Ｃ１～Ｃ６のアルキル基またはＣ１～Ｃ６のハロアルキル基を表し、Ｌは、Ｓ、ＳＯ、またはＳＯ２を表す。）、
    　　またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表す、請求項１に記載の化合物、またはその塩。     R1 is
    Cyano group,
    A C1-C6 alkyl group optionally substituted with a substituent A,
    A C1-C6 haloalkyl group,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A,
    A C2-C6 alkenyl group optionally substituted with a substituent A,
    A C2-C6 haloalkenyl group,
    A C2-C6 alkynyl group optionally substituted with a substituent A,
    Or a C2-C6 haloalkynyl group;
    R2, R3 and R4 are each independently;
    Hydrogen atom,
    Halogen atom,
    Hydroxyl group,
    Cyano group,
    A C1-C6 alkyl group optionally substituted with a substituent C,
    A C1-C6 haloalkyl group,
    A C2-C6 alkenyl group optionally substituted with a substituent C,
    A C2-C6 alkynyl group optionally substituted with a substituent C,
    A C1-C6 alkoxy group optionally substituted with a substituent C,
    C1-C6 haloalkoxy groups,
    A C2-C6 alkenyloxy group optionally substituted with a substituent C,
    A C2-C6 haloalkenyloxy group,
    A C3-C6 alkynyloxy group optionally substituted with a substituent C,
    A C3-C6 haloalkynyloxy group,
    An aralkyloxy group optionally substituted with 0 to 5 substituents D,
    Or Rx1C (＝ O) O— (where Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 , A C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN— (where Ra and Rb are each independently a hydrogen atom or a substituent B, It represents a good C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or Ra and Rb together with the nitrogen atom to be bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl , A piperidinyl group, a homopiperidinyl group, or an azocanyl group.).
    R5 is
    Hydrogen atom,
    Halogen atom,
    A C1-C6 alkyl group optionally substituted with a substituent A,
    A C1-C6 haloalkyl group,
    A C2-C6 alkenyl group optionally substituted with a substituent A,
    A C2-C6 alkynyl group optionally substituted with a substituent A,
    A C1-C6 alkoxy group optionally substituted with a substituent A,
    A C2-C6 alkenyloxy group optionally substituted with a substituent A,
    A C3-C6 alkynyloxy group optionally substituted with a substituent A,
    Or R51C (＝ O)-(where R51 is a hydroxyl group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, or a C1 Represents an alkoxy group of -C6);
    R6 is
    Halogen atom,
    Hydroxyl group,
    Cyano group,
    A C1-C6 alkyl group optionally substituted with a substituent C,
    A C1-C6 haloalkyl group,
    A C2-C6 alkenyl group optionally substituted with a substituent C,
    A C2-C6 alkynyl group optionally substituted with a substituent C,
    A C1-C6 alkoxy group optionally substituted with a substituent C,
    C1-C6 haloalkoxy groups,
    A C2-C6 alkenyloxy group optionally substituted with a substituent C,
    A C3-C6 alkynyloxy group optionally substituted with a substituent C,
    Rx1C (= O)-(where Rx1 is as defined above),
    Rc-L-(wherein, Rc represents a haloalkyl group of alkyl or C1 ~ C6 of C1 ~ C6, L represents S, SO, or SO 2.),
    2. The compound according to claim 1, which represents RaRbN- (where Ra and Rb are as defined above), or a salt thereof.
  3. 　Ｒ１は、
    　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　　またはＣ１～Ｃ６のハロアルキル基を表し；
    　Ｒ２、Ｒ３およびＲ４は、それぞれ独立していて、
    　　水素原子、
    　　ハロゲン原子、
    　　水酸基、
    　　シアノ基、
    　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　　または置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基を表し；
    　Ｒ５は、
    　　水素原子、
    　　ハロゲン原子、
    　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　　Ｃ１～Ｃ６のハロアルキル基、
    　　または置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基を表し；
    　Ｒ６は、
    　　ハロゲン原子、
    　　シアノ基、
    　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　　Ｃ１～Ｃ６のハロアルキル基、
    　　または置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基を表す、請求項２に記載の化合物、またはその塩。     R1 is
    A C1-C6 alkyl group optionally substituted with a substituent A,
    Or a C1-C6 haloalkyl group;
    R2, R3 and R4 are each independently;
    Hydrogen atom,
    Halogen atom,
    Hydroxyl group,
    Cyano group,
    A C1-C6 alkyl group optionally substituted with a substituent C,
    Or a C1-C6 alkoxy group optionally substituted with a substituent C;
    R5 is
    Hydrogen atom,
    Halogen atom,
    A C1-C6 alkyl group optionally substituted with a substituent A,
    A C1-C6 haloalkyl group,
    Or a C2-C6 alkynyl group optionally substituted with a substituent A;
    R6 is
    Halogen atom,
    Cyano group,
    A C1-C6 alkyl group optionally substituted with a substituent C,
    A C1-C6 haloalkyl group,
    3. The compound according to claim 2, which represents a C1 to C6 alkoxy group optionally substituted with a substituent C, or a salt thereof.
  4. 　式（２）
    Figure JPOXMLDOC01-appb-C000003
    　［式中、Ｒ２、Ｒ３およびＲ４は、それぞれ独立していて、
    　　水素原子、
    　　ハロゲン原子、
    　　水酸基、
    　　シアノ基、
    　　ニトロ基、
    　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　　Ｃ１～Ｃ６のハロアルキル基、
    　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　　Ｃ２～Ｃ６のハロアルケニル基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　　Ｃ２～Ｃ６のハロアルキニル基、
    　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　　Ｃ１～Ｃ６のハロアルコキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
    　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
    　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
    　　置換基Ｄで適宜０～５置換されてもよいアリールオキシ基、
    　　置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基、
    　　置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、
    　　Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、それぞれ独立していて、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表すか、あるいはＲａおよびＲｂは、結合する窒素原子と一緒になって、アジリジニル基、アゼチジニル基、ピロリジニル基、ピペリジニル基、ホモピペリジニル基、またはアゾカニル基を形成するものを表す。）を表す。）、
    　　Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、前記と同義である。）、
    　　１～２個の酸素原子を含む３～６員環の基、
    　　Ｒｃ－Ｌ－（ここで、Ｒｃは、Ｃ１～Ｃ６のアルキル基またはＣ１～Ｃ６のハロアルキル基を表し、Ｌは、Ｓ、ＳＯ、またはＳＯ２を表す。）、
    　　ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
    　　またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、またはＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）を表し、Ｒｘ３は、水素原子、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、またはＣ３～Ｃ８のシクロアルキル基を表す。）を表し；
    　Ｒ５は、
    　　水素原子、
    　　ハロゲン原子、
    　　シアノ基、
    　　ニトロ基、
    　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　　Ｃ１～Ｃ６のハロアルキル基、
    　　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　　Ｃ２～Ｃ６のハロアルケニル基、
    　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　　Ｃ２～Ｃ６のハロアルキニル基、
    　　置換基Ａで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　　Ｃ１～Ｃ６のハロアルコキシ基、
    　　置換基Ａで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
    　　置換基Ａで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
    　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
    　　置換基Ａで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
    　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
    　　Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
    　　ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
    　　またはＲ５１Ｃ（＝Ｏ）－（ここで、Ｒ５１は、水酸基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、またはＣ１～Ｃ６のアルコキシ基を表す。）を表し；
    　Ｘは、酸素原子または硫黄原子を表し；
    　Ｙは、式（ｙ－１）、または式（ｙ－２）
    Figure JPOXMLDOC01-appb-C000004
    を表し、
    　Ｒ６は、
    　　ハロゲン原子、
    　　水酸基、
    　　シアノ基、
    　　ニトロ基、
    　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルキル基、
    　　Ｃ１～Ｃ６のハロアルキル基、
    　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルキル基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニル基、
    　　Ｃ２～Ｃ６のハロアルケニル基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルキニル基、
    　　Ｃ２～Ｃ６のハロアルキニル基、
    　　置換基Ｃで適宜置換されてもよいＣ１～Ｃ６のアルコキシ基、
    　　Ｃ１～Ｃ６のハロアルコキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ８のシクロアルコキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ２～Ｃ６のアルケニルオキシ基、
    　　Ｃ２～Ｃ６のハロアルケニルオキシ基、
    　　置換基Ｃで適宜置換されてもよいＣ３～Ｃ６のアルキニルオキシ基、
    　　Ｃ３～Ｃ６のハロアルキニルオキシ基、
    　　置換基Ｄで適宜０～５置換されてもよいアリールオキシ基、
    　　置換基Ｄで適宜０～２置換されてもよいヘテロアリールオキシ基、
    　　置換基Ｄで適宜０～５置換されてもよいアラルキルオキシ基、
    　　Ｒｘ１Ｃ（＝Ｏ）－（ここで、Ｒｘ１は、前記と同義である。）、
    　　Ｒｘ１Ｃ（＝Ｏ）Ｏ－（ここで、Ｒｘ１は、前記と同義である。）、
    　　１～２個の酸素原子を含む３～６員環の基、
    　　Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、
    　　ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、
    　　またはＲｘ２Ｃ（＝Ｏ）Ｎ（Ｒｘ３）－（ここで、Ｒｘ２およびＲｘ３は、前記と同義である。）を表し；
    　ｎは、０～３の整数（ｎが２以上の場合、２以上のＲ６はそれぞれ独立した置換基を表す。）を表し；
    　そして、置換基Ａは、水酸基、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）およびＲｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）からなる群から選択される少なくとも１種であり；
    　置換基Ｂは、シアノ基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種であり；
    　置換基Ｃは、水酸基、シアノ基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基、Ｃ３～Ｃ８のシクロアルコキシ基、Ｃ２～Ｃ６のアルコキシアルコキシ基、ＲａＲｂＮ－（ここで、ＲａおよびＲｂは、前記と同義である。）、Ｒｃ－Ｌ－（ここで、ＲｃおよびＬは、前記と同義である。）、ＲｄＣ（＝Ｏ）－（ここで、Ｒｄは、前記のＲｘ１と同義である。）および１～２個の酸素原子を含む３～６員環の基からなる群から選択される少なくとも１種であり；
    　置換基Ｄは、ハロゲン原子、水酸基、シアノ基、ニトロ基、置換基Ｂで適宜置換されてもよいＣ１～Ｃ６のアルキル基、Ｃ１～Ｃ６のハロアルキル基、Ｃ３～Ｃ８のシクロアルキル基、Ｃ１～Ｃ６のアルコキシ基、Ｃ１～Ｃ６のハロアルコキシ基およびＣ３～Ｃ８のシクロアルコキシ基からなる群から選択される少なくとも１種である。］で表される化合物、またはその塩。     Equation (2)
    Figure JPOXMLDOC01-appb-C000003
    Wherein R2, R3 and R4 are each independently
    Hydrogen atom,
    Halogen atom,
    Hydroxyl group,
    Cyano group,
    Nitro group,
    A C1-C6 alkyl group optionally substituted with a substituent C,
    A C1-C6 haloalkyl group,
    A C3-C8 cycloalkyl group optionally substituted with a substituent C,
    A C2-C6 alkenyl group optionally substituted with a substituent C,
    A C2-C6 haloalkenyl group,
    A C2-C6 alkynyl group optionally substituted with a substituent C,
    A C2-C6 haloalkynyl group,
    A C1-C6 alkoxy group optionally substituted with a substituent C,
    C1-C6 haloalkoxy groups,
    A C3-C8 cycloalkoxy group optionally substituted with a substituent C,
    A C2-C6 alkenyloxy group optionally substituted with a substituent C,
    A C2-C6 haloalkenyloxy group,
    A C3-C6 alkynyloxy group optionally substituted with a substituent C,
    A C3-C6 haloalkynyloxy group,
    An aryloxy group optionally substituted with 0 to 5 substituents D,
    A heteroaryloxy group optionally substituted with 0 to 2 substituents D,
    An aralkyloxy group optionally substituted with 0 to 5 substituents D,
    Rx1C (＝ O)-(where Rx1 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group which may be appropriately substituted with a substituent B A group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (where Ra and Rb are each independently a hydrogen atom or a C1 which may be appropriately substituted with a substituent B) Represents an alkyl group of -C6, a haloalkyl group of C1-C6, or a cycloalkyl group of C3-C8, or Ra and Rb together with the nitrogen atom to which they are attached form an aziridinyl group, azetidinyl group, pyrrolidinyl group, Which forms a piperidinyl group, a homopiperidinyl group, or an azocanyl group)).
    Rx1C (= O) O- (where Rx1 is as defined above),
    A 3-6 membered ring group containing 1-2 oxygen atoms,
    Rc-L-(wherein, Rc represents a haloalkyl group of alkyl or C1 ~ C6 of C1 ~ C6, L represents S, SO, or SO 2.),
    RaRbN- (where Ra and Rb are as defined above),
    Or Rx2C (= O) N (Rx3)-(where Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl Represents an alkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN— (where Ra and Rb have the same meanings as described above), and Rx3 represents , A hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group which may be optionally substituted with a substituent B);
    R5 is
    Hydrogen atom,
    Halogen atom,
    Cyano group,
    Nitro group,
    A C1-C6 alkyl group optionally substituted with a substituent A,
    A C1-C6 haloalkyl group,
    A C3-C8 cycloalkyl group optionally substituted with a substituent A,
    A C2-C6 alkenyl group optionally substituted with a substituent A,
    A C2-C6 haloalkenyl group,
    A C2-C6 alkynyl group optionally substituted with a substituent A,
    A C2-C6 haloalkynyl group,
    A C1-C6 alkoxy group optionally substituted with a substituent A,
    C1-C6 haloalkoxy groups,
    A C3-C8 cycloalkoxy group optionally substituted with a substituent A,
    A C2-C6 alkenyloxy group optionally substituted with a substituent A,
    A C2-C6 haloalkenyloxy group,
    A C3-C6 alkynyloxy group optionally substituted with a substituent A,
    A C3-C6 haloalkynyloxy group,
    Rc-L- (where Rc and L are as defined above),
    RaRbN- (where Ra and Rb are as defined above),
    Or R51C (＝ O)-(where R51 is a hydroxyl group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, or a C1 Represents an alkoxy group of -C6);
    X represents an oxygen atom or a sulfur atom;
    Y is the formula (y-1) or the formula (y-2)
    Figure JPOXMLDOC01-appb-C000004
    Represents
    R6 is
    Halogen atom,
    Hydroxyl group,
    Cyano group,
    Nitro group,
    A C1-C6 alkyl group optionally substituted with a substituent C,
    A C1-C6 haloalkyl group,
    A C3-C8 cycloalkyl group optionally substituted with a substituent C,
    A C2-C6 alkenyl group optionally substituted with a substituent C,
    A C2-C6 haloalkenyl group,
    A C2-C6 alkynyl group optionally substituted with a substituent C,
    A C2-C6 haloalkynyl group,
    A C1-C6 alkoxy group optionally substituted with a substituent C,
    C1-C6 haloalkoxy groups,
    A C3-C8 cycloalkoxy group optionally substituted with a substituent C,
    A C2-C6 alkenyloxy group optionally substituted with a substituent C,
    A C2-C6 haloalkenyloxy group,
    A C3-C6 alkynyloxy group optionally substituted with a substituent C,
    A C3-C6 haloalkynyloxy group,
    An aryloxy group optionally substituted with 0 to 5 substituents D,
    A heteroaryloxy group optionally substituted with 0 to 2 substituents D,
    An aralkyloxy group optionally substituted with 0 to 5 substituents D,
    Rx1C (= O)-(where Rx1 is as defined above),
    Rx1C (= O) O- (where Rx1 is as defined above),
    A 3-6 membered ring group containing 1-2 oxygen atoms,
    Rc-L- (where Rc and L are as defined above),
    RaRbN- (where Ra and Rb are as defined above),
    Or Rx2C (= O) N (Rx3)-(where Rx2 and Rx3 are as defined above);
    n represents an integer of 0 to 3 (when n is 2 or more, 2 or more R6 each represents an independent substituent);
    The substituent A is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, RaRbN- (where Ra And Rb are as defined above, and Rc-L- (wherein Rc and L are as defined above), and are at least one selected from the group consisting of:
    Substituent B is at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group;
    Substituent C is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN -(Where Ra and Rb are as defined above), Rc-L- (where Rc and L are as defined above), RdC (= O)-(where Rd Is the same as defined above for Rx1), and is at least one member selected from the group consisting of a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
    Substituent D is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C8 It is at least one selected from the group consisting of a C6 alkoxy group, a C1 to C6 haloalkoxy group and a C3 to C8 cycloalkoxy group. Or a salt thereof.
  5. 　請求項１に記載の化合物、またはその塩を有効成分として含有する農園芸用有害生物防除剤。 農 A pest control agent for agricultural and horticultural use containing the compound according to claim 1 or a salt thereof as an active ingredient.
  6. 　請求項１に記載の化合物、またはその塩を有効成分として含有する農園芸用殺菌剤。 農 An agricultural and horticultural fungicide containing the compound according to claim 1 or a salt thereof as an active ingredient.
  7. 　請求項５に記載の農園芸用有害生物防除剤を、植物、植物の種子、または植物を栽培する土壌に施用することを含む、植物病害を防除する方法。 方法 A method for controlling plant diseases, comprising applying the pesticidal composition for agricultural and horticultural use according to claim 5 to a plant, a plant seed, or a soil in which the plant is grown.
  8. 　請求項６に記載の農園芸用殺菌剤を、植物、植物の種子、または植物を栽培する土壌に施用することを含む、植物病害を防除する方法。 A method for controlling plant diseases, which comprises applying the fungicide for agricultural and horticultural use according to claim 6 to a plant, a seed of a plant, or soil in which the plant is grown.
PCT/JP2019/028942 2018-07-24 2019-07-24 Pyridone compound and agricultural and horticultural fungicide having this as active component WO2020022360A1 (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009137651A2 (en) * 2008-05-08 2009-11-12 E. I. Du Pont De Nemours And Company Fungicidal substituted azoles
WO2012009227A1 (en) * 2010-07-16 2012-01-19 N30 Pharmaceuticals, Llc Novel dihydropyridin-2(1h)-one compounds as s-nitrosoglutathione reductase inhibitors and neurokinin-3 receptor antagonists
JP2014101317A (en) * 2012-11-20 2014-06-05 Nissan Chem Ind Ltd Substituted pyridazine compound and agricultural/horticultural germicide
WO2017061525A1 (en) * 2015-10-09 2017-04-13 三井化学アグロ株式会社 Pyridone compound and agricultural/horticultural bactericide including same as active ingredient

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009137651A2 (en) * 2008-05-08 2009-11-12 E. I. Du Pont De Nemours And Company Fungicidal substituted azoles
WO2012009227A1 (en) * 2010-07-16 2012-01-19 N30 Pharmaceuticals, Llc Novel dihydropyridin-2(1h)-one compounds as s-nitrosoglutathione reductase inhibitors and neurokinin-3 receptor antagonists
JP2014101317A (en) * 2012-11-20 2014-06-05 Nissan Chem Ind Ltd Substituted pyridazine compound and agricultural/horticultural germicide
WO2017061525A1 (en) * 2015-10-09 2017-04-13 三井化学アグロ株式会社 Pyridone compound and agricultural/horticultural bactericide including same as active ingredient

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