WO2020036133A1 - 3-(1h-1,2,4-triazole-1-yl) benzoic acid amide derivative and harmful organism control agent - Google Patents

3-(1h-1,2,4-triazole-1-yl) benzoic acid amide derivative and harmful organism control agent Download PDF

Info

Publication number
WO2020036133A1
WO2020036133A1 PCT/JP2019/031563 JP2019031563W WO2020036133A1 WO 2020036133 A1 WO2020036133 A1 WO 2020036133A1 JP 2019031563 W JP2019031563 W JP 2019031563W WO 2020036133 A1 WO2020036133 A1 WO 2020036133A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
alkyl
cycloalkyl
substituted
optionally substituted
Prior art date
Application number
PCT/JP2019/031563
Other languages
French (fr)
Japanese (ja)
Inventor
幸浩 榎本
大介 志鎌
皓祐 田中
啓二 鳥谷部
義浩 村松
阿部　晋
陽 高根澤
松田　武
Original Assignee
クミアイ化学工業株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by クミアイ化学工業株式会社 filed Critical クミアイ化学工業株式会社
Publication of WO2020036133A1 publication Critical patent/WO2020036133A1/en

Links

Classifications

    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a novel 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or an agriculturally acceptable salt thereof, and a pest control containing the derivative or its salt as an active ingredient. It relates to an agent and a production intermediate.
  • Patent Documents 1 and 2 describe 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivatives having a pest control effect.
  • the compounds described in Patent Documents 1 and 2 are limited to compounds in which a 1H-pyrazol-5-yl group is bonded to the 3-position of a triazole ring bonded to the 3-position of benzoic acid amide.
  • Patent Document 3 describes a 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative having P2X3 or P2X2 / 3 receptor antagonist activity.
  • the compounds described in Patent Document 3 are limited to compounds in which a 5-methylpyridin-2-yl group is bonded to the 5-position of benzoic acid amide. Furthermore, Patent Document 3 has no description on insecticidal activity.
  • Patent Document 4 describes a benzoic acid amide derivative having P2X7 receptor inhibitory activity.
  • the compound described in Patent Document 4 is a compound in which a 4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl group is bonded to the 3-position of benzoic acid amide, Limited to-(hydroxy-substituted cycloalkylalkyl) benzoic acid amides. Further, Patent Document 4 has no description on insecticidal activity.
  • Patent Document 5 describes a phenylsulfamoylcarboxamide derivative having herbicidal activity.
  • the compound described in Patent Document 5 is limited to a compound in which a 4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl group is bonded to the 3-position of phenylsulfamoylcarboxamide. ing. Furthermore, Patent Document 5 has no description on insecticidal activity.
  • Patent Document 6 describes a 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative having factor Xa inhibitory activity.
  • the compounds described in Patent Document 6 are limited to compounds in which a phenylaminocarbonyl group, a pyridylaminocarbonyl group, and a pyrimidinylaminocarbonyl group are bonded to the 5-position of a triazole ring. Furthermore, Patent Document 6 has no description on insecticidal activity.
  • Pest control agents used for useful crops are desired to be applied to soil or foliage and show sufficient pest control effects at a low dose.
  • the demand for the safety of chemical substances and the effect on the environment has been increasing, and the development of safer pest control agents has been desired.
  • pesticides such as insecticides, acaricides, nematodes, etc. for many years, pests that have acquired resistance to the pesticides have emerged. It has become difficult to completely control pests.
  • the use of pesticides with high human toxicity is a problem in terms of safety for workers.
  • an object of the present invention is to solve the above-mentioned problems of a conventional pest control agent, and furthermore, to provide a pest excellent in safety, control effect, residual effect and the like.
  • An object of the present invention is to provide a controlling agent and a novel compound therefor.
  • the present inventors have synthesized various 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivatives and developed their pest control agents having the above-mentioned preferable properties. We studied diligently about physiological activity. As a result, 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivatives (hereinafter, also referred to as compounds of the present invention) represented by the following general formula [I] can be used for various pests.
  • the present invention has been found to have an excellent control effect on, and the present invention has been completed by further study.
  • R 11 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano C A 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or A C 3 -C 6 halocycloalkyl group;
  • R 12 is a hydrogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C
  • a 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or an agriculturally acceptable salt thereof represented by the formula: (2) An agrochemical composition containing the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or the agriculturally acceptable salt thereof according to (1) as an active ingredient. (3) The pesticidal composition according to (2), wherein the pesticidal composition further contains a surfactant.
  • a pest control agent comprising the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or the agriculturally acceptable salt thereof according to the above (1) as an active ingredient.
  • the pest control agent according to the above (4) wherein the pest control agent is an insecticide, a nematicide, and an acaricide.
  • the harmful substance according to the above (5) which has a controlling effect on pests in paddy fields, fields, turf, orchards, non-agricultural lands, greenhouses, nursery facilities, and plant factories for cultivating agricultural and horticultural plants. Biocontrol agents.
  • K represents -OH, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkoxy group, a phenyloxy group or a phenyl C 1 -C 6 alkoxy group which is unsubstituted or substituted by (Z) p 1 ;
  • R 11 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano C A 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or A C 3 -C 6 halocycloalkyl group;
  • R 12 is a hydrogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C
  • R 11 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano C A 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or A C 3 -C 6 halocycloalkyl group;
  • R 12 is a hydrogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C
  • a 1-phenyl-1H-1,2,4-triazole derivative or a salt thereof which is represented by the following formula: (16) The 3- (1H-1) according to (1), wherein the 1-phenyl-1H-1,2,4-triazole derivative or the salt thereof according to (15) is used as a raw material. , 2,4-triazol-1-yl) benzoic acid amide derivatives.
  • the compound represented by the general formula [I] of the present invention has an excellent pest control effect, and includes stink bugs, lepidoptera, pests, flies, pests, wasps, thrips, and thrips. It shows an excellent control effect on a wide range of pests such as eye pests, spider mites and plant parasitic nematodes, and can also control pests that have acquired drug resistance.
  • pest control agents containing the compound of the present invention spider mites, spider mites, Mandarin spider mites, spider mites, etc .; It is highly effective against nematodes such as representatives of the order Lepidoptera and root-knot nematodes, and insects of the order Lepidoptera such as Japanese moth, P. persica, and Tobacco. In addition, because of its excellent permeability, a safe and labor-saving application method by soil treatment is possible.
  • the term “pesticide” means animals such as agricultural and horticultural fields, livestock and pets, and insecticides, acaricides, nematocides, etc. for domestic or epidemic control.
  • halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the notation such as “C 1 -C 6 ” indicates that the number following the element symbol indicates the number of carbon atoms.
  • the number of carbon atoms may be any of 1 to 6 I have.
  • the “C 1 -C 6 alkyl group” refers to a linear or branched alkyl group having 1 to 6 carbon atoms, unless otherwise specified.
  • C 1 -C 6 haloalkyl group means a straight-chain or branched-chain C 1 -C 6 substituted with 1 to 13 halogen atoms which are the same or different, unless otherwise specified.
  • Represents a haloalkyl group for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, iodomethyl, chlorodifluoromethyl, dichlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1-chloroethyl, 2 -Chloroethyl, 1,1
  • C 3 -C 6 cycloalkyl group refers to a cycloalkyl group having 3 to 6 carbon atoms unless otherwise specified, and examples thereof include groups such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Can be.
  • C 3 -C 6 halocycloalkyl group refers to a cycloalkyl group having 3 to 6 carbon atoms, which is substituted with the same or different 1 to 11 halogen atoms, unless otherwise specified.
  • C 2 -C 6 alkenyl group refers to a linear or branched alkenyl group having 2 to 6 carbon atoms unless otherwise specified, and examples thereof include vinyl, 1-propenyl, isopropenyl, 2-propenyl, 1-butenyl, 1-methyl-1-propenyl, 2-butenyl, 1-methyl-2-propenyl, 3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1, 3-butadienyl, 1-pentenyl, 1-ethyl-2-propenyl, 2-pentenyl, 1-methyl-1-butenyl, 3-pentenyl, 1-methyl-2-butenyl, 4-pentenyl, 1-methyl-3- Butenyl, 3-methyl-1-butenyl, 1,2-dimethyl-2-propenyl, 1,1-dimethyl-2-propenyl, 2-methyl-2-butenyl, 3-methyl-2 Butenyl, 1,2-dimethyl-1-
  • C 2 -C 6 haloalkenyl group means a linear or branched C 2 -C 6 substituted with 1 to 11 halogen atoms, which is the same or different, unless otherwise specified. And represents, for example, 1-fluorovinyl, 2-fluorovinyl, 1,2-difluorovinyl, 2,2-difluorovinyl, trifluorovinyl, 1-chlorovinyl, 2-chlorovinyl, 1,2-dichloro Vinyl, 2,2-dichlorovinyl, trichlorovinyl, 1,2-dibromovinyl, 2,2-dibromovinyl, tribromovinyl, 1,2-diiodomovinyl, 2,2-diiodovinyl, triiodovinyl, 1-fluoro- 2-propenyl, 2-fluoro-2-propenyl, 3-fluoro-2-propenyl, 2,3-difluor
  • C 2 -C 6 alkynyl group means a linear or branched alkynyl group having 2 to 6 carbon atoms, unless otherwise specified.
  • C 2 -C 6 haloalkynyl group means a straight-chain or branched-chain having 2 to 6 carbon atoms substituted with the same or different 1 to 9 halogen atoms, unless otherwise specified.
  • C 1 -C 6 alkoxy group means a (C 1 -C 6 alkyl) —O— group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified, and includes, for example, methoxy, ethoxy, n -Propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy , 1,2-dimethylpropoxy or n-hexyloxy.
  • C 1 -C 6 haloalkoxy group means a (C 1 -C 6 haloalkyl) -O— group in which the haloalkyl moiety has the above-mentioned meaning, unless otherwise specified.
  • the “C 2 -C 6 alkenyloxy group” refers to a (C 2 -C 6 alkenyl) -O— group in which the alkenyl moiety has the above-mentioned meaning, unless otherwise specified.
  • 2-propenyloxy group 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-butenyloxy, 3-butenyloxy, 3-methyl-2-butenyloxy, 4-methyl-3-butenyloxy, 4-pentenyloxy or 5- Examples include hexenyloxy and the like.
  • C 2 -C 6 haloalkenyloxy group means a (C 2 -C 6 haloalkenyl) -O— group in which the haloalkenyl portion has the above-mentioned meaning, unless otherwise specified.
  • the “C 2 -C 6 alkynyloxy group” means a (C 2 -C 6 alkynyl) -O— group in which the alkynyl moiety has the above-mentioned meaning, unless otherwise specified.
  • 2-propynyloxy 1-methyl-2-propynyloxy, 1-ethyl-2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-butynyloxy, 2-pentynyloxy, 4-pentynyloxy or 4,4 -Dimethyl-2-pentynyloxy and the like.
  • C 2 -C 6 haloalkynyloxy group means a (C 2 -C 6 haloalkynyl) —O— group in which the haloalkynyl moiety has the above-mentioned meaning, unless otherwise specified.
  • C 3 -C 6 cycloalkyloxy group means a (C 3 -C 6 cycloalkyl) -O— group in which the cycloalkyl moiety has the above-mentioned meaning, unless otherwise specified.
  • Examples include groups such as propoxy, cyclobutoxy, cyclopentyloxy or cyclohexyloxy.
  • C 3 -C 6 halocycloalkyloxy group means a (C 3 -C 6 halocycloalkyl) -O— group in which the halocycloalkyl moiety has the above-mentioned meaning, unless otherwise limited.
  • 2,2-difluorocyclopropoxy, 2,2-dichlorocyclopropoxy, 3,3-difluorocyclobutoxy, 3,3-dichlorocyclobutoxy, 3-fluorocyclopentyloxy, 3,3-difluorocyclopentyloxy, nonafluoro Examples include groups such as cyclopentyloxy, 3,3-dichlorocyclopentyloxy, 4,4-difluorocyclohexyloxy, and 4,4-dichlorocyclohexyloxy.
  • aromatic heterocyclic oxy group means a (aromatic heterocyclic) -O— group in which the aromatic heterocyclic moiety has the above-mentioned meaning, unless otherwise specified.
  • aromatic heterocyclic oxy group means a (aromatic heterocyclic) -O— group in which the aromatic heterocyclic moiety has the above-mentioned meaning, unless otherwise specified.
  • pyridin-2-yloxy Pyridin-3-yloxy, pyridin-4-yloxy, pyrazin-2-yloxy, pyridazin-3-yloxy, pyridazin-4-yloxy, pyrimidin-2-yloxy, pyrimidin-4-yloxy, pyrimidin-5-yloxy, thiazole Groups such as -2-yloxy, thiazol-4-yloxy or thiazol-5-yloxy.
  • the “saturated heterocyclic oxy group” refers to a (saturated heterocyclic) -O— group in which the saturated heterocyclic moiety has the above-mentioned meaning, unless otherwise specified.
  • oxetane-3-yloxy, tetrahydrofuran- Such as 2-yloxy, tetrahydrofuran-3-yloxy, (tetrahydro-2H-pyran-2-yl) oxy, (tetrahydro-2H-pyran-3-yl) oxy or (tetrahydro-2H-pyran-4-yl) oxy; Groups.
  • C 1 -C 6 alkylthio group refers to a (C 1 -C 6 alkyl) -S— group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified.
  • Examples include groups such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, pentylsulfinyl and hexylsulfinyl.
  • Examples include groups such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, pentylsulfonyl and hexylsulfonyl.
  • the “C 1 -C 6 haloalkylthio group” refers to a (C 1 -C 6 haloalkyl) -S— group in which the haloalkyl moiety has the above-mentioned meaning, unless otherwise specified, and includes, for example, fluoromethylthio, difluoro Methylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, pentafluoroethylthio, 2,2,2-trichloroethylthio, 3,3,3-trifluoropropylthio, 1,1, 2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1,1,1,3,3,3-hexafluoropropan-2-ylthio, heptafluoropropan-2-ylthio or 4,4 Examples include groups such as 4-trifluorobutylthio
  • difluoromethylsulfonyl difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, 3,3,3-trifluoropropylsulfonyl, heptafluoropropylsulfonyl, or heptafluoro- Examples include groups such as 2-propylsulfonyl.
  • C 2 -C 6 alkenylthio group refers to a (C 2 -C 6 alkenyl) -S— group in which the alkenyl moiety has the above-mentioned meaning, unless otherwise specified.
  • 2-propenylthio group 2-butenylthio, 3-butenylthio, 2-pentenylthio, 3-pentenylthio, 4-pentenylthio, 2-methyl-2-butenylthio, 2,4-pentadienylthio, 2-hexenylthio, 3-hexenylthio , 4-hexenylthio, 5-hexenylthio or 2,4-hexadienylthio.
  • groups such as sulfonyl, 2-hexenylsulfonyl, 3-hexenylsulfonyl, 4-hexenylsulfonyl, 5-hexenylsulfonyl, and 2,4-hexadienylsulfonyl.
  • C 2 -C 6 haloalkenylthio group means a (C 2 -C 6 haloalkenyl) -S— group in which the alkenyl moiety has the above-mentioned meaning, unless otherwise specified.
  • 3-chloro-2-propenylsulfinyl 3,3-dichloro-2-propenylsulfinyl, 3,3-difluoro-2-propenylsulfinyl, 3,3,3-trifluoro-1-propenylsulfinyl, 2,3 , 3,3-tetrafluoro-1-propenylsulfinyl, 4,4,4-trifluoro-2-butenylsulfinyl, 3,4,4-trifluoro-3-butenylsulfinyl, 5-chloro-3-pentenyl
  • groups include groups such as sulfinyl and 6-fluoro-2-hexenylsulfinyl.
  • 3-chloro-2-propenylsulfonyl 3,3-dichloro-2-propenylsulfonyl, 3,3-difluoro-2-propenylsulfonyl, 3,3,3-trifluoro-1-propenylsulfonyl, 2, 3,3,3-tetrafluoro-1-propenylsulfonyl, 4,4,4-trifluoro-2-butenylsulfonyl, 3,4,4-trifluoro-3-butenylsulfonyl, 5-chloro-3- Examples include groups such as pentenylsulfonyl and 6-fluoro-2-hexenylsulfonyl.
  • C 2 -C 6 alkynylthio group means a (C 2 -C 6 alkynyl) -S— group in which the alkynyl moiety has the above-mentioned meaning, unless otherwise specified.
  • Groups such as -butyn-3-ylthio, 3-methyl-1-butyn-3-ylthio, 2-butynylthio, 3-butynylthio, 2-pentynylthio, 3-pentynylthio, 4-pentynylthio or 5-hexynylthio. .
  • C 3 -C 6 cycloalkylthio group means a (C 3 -C 6 cycloalkyl) -S— group in which the cycloalkyl moiety has the above-mentioned meaning, unless otherwise specified.
  • Groups such as thio, cyclobutylthio, cyclopentylthio or cyclohexylthio can be mentioned.
  • examples thereof include groups such as cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, and cyclohexylsulfinyl.
  • the “aromatic heterocyclic thio group” refers to a (aromatic heterocyclic) -S— group in which the aromatic heterocyclic moiety has the above-mentioned meaning, unless otherwise specified.
  • aromatic heterocyclic thio refers to a (aromatic heterocyclic) -S— group in which the aromatic heterocyclic moiety has the above-mentioned meaning, unless otherwise specified.
  • pyridin-2-ylthio Pyridin-3-ylthio, pyridin-4-ylthio, pyrazin-2-ylthio, pyridazin-3-ylthio, pyridazin-4-ylthio, pyrimidin-2-ylthio, pyrimidin-4-ylthio, pyrimidin-5-ylthio, thiazole
  • groups such as -2-ylthio, thiazol-4-ylthio or thiazol-5-ylthio.
  • -2-ylsulfinyl pyridin-3-ylsulfinyl, pyridin-4-ylsulfinyl, pyrazin-2-ylsulfinyl, pyridazin-3-ylsulfinyl, pyridazin-4-ylsulfinyl, pyrimidin-2-ylsulfinyl, pyrimidine- Examples include groups such as 4-ylsulfinyl, pyrimidin-5-ylsulfinyl, thiazol-2-ylsulfinyl, thiazol-4-ylsulfinyl, and thiazol-5-ylsulfinyl.
  • saturated heterocyclic thio group means a (saturated heterocyclic) -S— group in which the saturated heterocyclic moiety has the above-mentioned meaning, unless otherwise specified.
  • saturated heterocyclic thio group means a (saturated heterocyclic) -S— group in which the saturated heterocyclic moiety has the above-mentioned meaning, unless otherwise specified.
  • oxetane-3-ylthio, tetrahydrofuran- such as 2-ylthio, tetrahydrofuran-3-ylthio, (tetrahydro-2H-pyran-2-yl) thio, (tetrahydro-2H-pyran-3-yl) thio or (tetrahydro-2H-pyran-4-yl) thio Groups.
  • a “saturated heterocyclic sulfinyl group” means a (saturated heterocyclic) -S ((O) — group in which the saturated heterocyclic moiety has the above-mentioned meaning, unless otherwise specified.
  • oxetane-3- Ylsulfinyl tetrahydrofuran-2-ylsulfinyl, tetrahydrofuran-3-ylsulfinyl, (tetrahydro-2H-pyran-2-yl) sulfinyl, (tetrahydro-2H-pyran-3-yl) sulfinyl or (tetrahydro-2H-pyran- 4-yl) sulfinyl and the like.
  • saturated heterocyclic sulfonyl group means a (saturated heterocyclic) -S (OO) 2 — group in which the saturated heterocyclic moiety has the above-mentioned meaning, unless otherwise specified.
  • oxetane-3 -Ylsulfonyl tetrahydrofuran-2-ylsulfonyl, tetrahydrofuran-3-ylsulfonyl, (tetrahydro-2H-pyran-2-yl) sulfonyl, (tetrahydro-2H-pyran-3-yl) sulfonyl or (tetrahydro-2H-pyran -4-yl) sulfonyl and the like.
  • C 1 -C 6 alkoxy C 1 -C 6 alkyl group means that the alkoxy portion and the alkyl portion have the same meanings as described above, unless otherwise specified (C 1 -C 6 alkoxy)-(C 1 To C 6 alkyl) groups, for example, methoxymethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-methoxy-1-methylethyl, 2-methoxyethyl, And groups such as -ethoxyethyl, 2-ethoxyethyl, 2-isopropoxyethyl, 3-methoxypropyl, 2-methoxypropyl, 3-ethoxypropyl, 4-methoxybutyl or 4-ethoxybutyl.
  • C 1 -C 6 alkylthio C 1 -C 6 alkyl group means, unless otherwise specified, an alkylthio moiety and an alkyl moiety having the above meaning (C 1 -C 6 alkylthio)-(C 1 -C 6 alkyl) group, for example, methylthiomethyl, 2- (methylthio) ethyl, 3- (methylthio) propyl, 4- (methylthio) butyl, ethylthiomethyl, propylthiomethyl, butylthiomethyl or pentylthiomethyl And the group of
  • the “cyano C 1 -C 6 alkyl group” means a (cyano)-(C 1 -C 6 alkyl) group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified.
  • Groups such as -cyanoethyl, 2-cyanoethyl, 3-cyanopropyl, 2-cyanopropan-2-yl, 1-cyanobutyl, 4-cyanobutyl, 5-cyanopentyl or 6-cyanohexyl.
  • phenyl C 1 -C 6 alkyl group means a phenyl- (C 1 -C 6 alkyl) group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified. Examples include groups such as ethyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl, and 6-phenylhexyl.
  • phenyl C 1 -C 6 alkoxy group means a phenyl- (C 1 -C 6 alkoxy) group in which the alkoxy moiety has the above-mentioned meaning, unless otherwise specified.
  • examples include groups such as phenylethyloxy, 2-phenylethyloxy, 3-phenylpropyloxy, 4-phenylbutyloxy, 5-phenylpentyloxy, and 6-phenylhexyloxy.
  • aromatic heterocyclic C 1 -C 6 alkyl group means an aromatic heterocyclic ring- (C 1 -C 6 alkyl) in which the aromatic heterocyclic ring and the alkyl portion have the above-mentioned meanings, unless otherwise specified.
  • the “saturated heterocyclic C 1 -C 6 alkyl group” means a saturated heterocyclic ring and a saturated heterocyclic- (C 1 -C 6 alkyl) group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified.
  • “mono (C 1 -C 6 alkyl) amino group” means a (C 1 -C 6 alkyl) -NH— group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified. Examples include groups such as amino, ethylamino or n-propylamino.
  • di (C 1 -C 6 alkyl) amino group means a (C 1 -C 6 alkyl) 2 —N— group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified.
  • the alkyl groups may be different from each other and include, for example, groups such as dimethylamino, methylethylamino and methyl-n-propylamino.
  • examples thereof include groups such as methylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino, isopropylsulfonylamino and tert-butylsulfonylamino.
  • the term “di (C 1 -C 6 alkyl) aminocarbonyl group” means that the alkyl portion has the above-mentioned meaning (C 1 -C 6 alkyl) 2 —NC (CO), unless otherwise specified. )-, And the two alkyl groups may be different from each other, and examples thereof include groups such as dimethylaminocarbonyl, diethylaminocarbonyl and diisopropylaminocarbonyl.
  • the term “mono (C 1 -C 6 haloalkyl) aminocarbonyl group” means that the haloalkyl moiety has the above-mentioned meaning, unless otherwise specified.
  • (C 1 -C 6 haloalkyl) -NH—C ( O)
  • notations such as “C 1 -C 6 alkyl group optionally substituted by R 7 ” and “C 1 -C 6 alkyl group optionally substituted by R 13 ” refer to hydrogen bonded to a carbon atom.
  • any R 7 or R 13 represents a substituted alkyl group, the number of R 7 or R 13 are substituted are selected arbitrarily in the range of number of carbon atoms of each of the specified.
  • each R 7 or R 13 may be the same or different from each other.
  • the notation such as "C 1 ⁇ C 6 haloalkyl group optionally substituted by R 13" by any R 13 is a hydrogen atom bonded to a carbon atom, a substituted haloalkyl group, substituted
  • the number of R 13 is arbitrarily selected within the range of the specified number of carbon atoms.
  • each R 13 may be the same or different from each other.
  • the notation such as "C 3 ⁇ C 6 cycloalkyl group optionally substituted by R 8 'is, by any R 8 is a hydrogen atom bonded to a carbon atom, a substituted cycloalkyl group,
  • the number of substituted R 8 is arbitrarily selected within the range of each specified number of carbon atoms.
  • each R 8 may be the same or different from each other.
  • the notation such as "C 2 ⁇ C 6 alkenyl group optionally substituted by R 13" by any R 13 is hydrogen atoms bonded to carbon atoms, a substituted alkenyl group, substituted
  • the number of R 13 is arbitrarily selected within the range of the specified number of carbon atoms.
  • each R 13 may be the same as or different from each other.
  • the notation such as "C 2 ⁇ C 6 alkynyl group optionally substituted by R 13" by any R 13 is a hydrogen atom bonded to a carbon atom, a substituted alkynyl group optionally
  • the number of R 13 to be substituted is arbitrarily selected within the range of each specified number of carbon atoms.
  • each R 13 may be the same as or different from each other.
  • notations such as “C 1 -C 6 alkoxy group optionally substituted by R 7 ” and “C 1 -C 6 alkoxy group optionally substituted by R 13 ” refer to hydrogen bonded to a carbon atom. by atomic any R 7 or R 13, represents a substituted alkoxy group, the number of R 7 or R 13 are substituted are selected arbitrarily in the range of number of carbon atoms of each of the specified. When two or more substituents R 7 or R 13 on the alkoxy group are present, each R 7 or R 13 may be the same or different from each other.
  • the notation such as "C 1 ⁇ C 6 haloalkoxy group optionally substituted by R 13" are hydrogen atoms bonded to carbon atoms by any R 13, represents a substituted haloalkoxy group,
  • the number of R 13 to be substituted is arbitrarily selected within the range of each specified number of carbon atoms.
  • each R 13 may be the same or different from each other.
  • the notation such as "C 1 ⁇ C 6 alkylthio group optionally substituted by R 13" by any R 13 is a hydrogen atom bonded to a carbon atom, a substituted alkylthio group, substituted
  • the number of R 13 is arbitrarily selected within the range of the specified number of carbon atoms.
  • each R 13 may be the same or different from each other.
  • the notation such as "optionally substituted C 1 ⁇ C 6 alkylsulfinyl group by R 13" by any R 13 is a hydrogen atom bonded to a carbon atom, a substituted alkylsulfinyl group,
  • the number of R 13 to be substituted is arbitrarily selected within the range of each specified number of carbon atoms.
  • each R 13 may be the same as or different from each other.
  • the notation such as "C 1 ⁇ C 6 alkylsulfonyl group optionally substituted by R 13" by any R 13 is a hydrogen atom bonded to a carbon atom, a substituted alkylsulfonyl group,
  • the number of R 13 to be substituted is arbitrarily selected within the range of each specified number of carbon atoms.
  • each R 13 may be the same as or different from each other.
  • the notation such as "C 1 ⁇ C 6 haloalkylthio group optionally substituted by R 13" by any R 13 is a hydrogen atom attached to the carbon atom, a substituted haloalkylthio group,
  • the number of R 13 to be substituted is arbitrarily selected within the range of each specified number of carbon atoms.
  • each R 13 may be the same as or different from each other.
  • the notation such as "C 1 ⁇ C 6 haloalkylsulfinyl group optionally substituted by R 13" by any R 13 is a hydrogen atom bonded to a carbon atom, a substituted haloalkylsulfinyl group,
  • the number of R 13 to be substituted is arbitrarily selected within the range of each specified number of carbon atoms.
  • each R 13 may be the same as or different from each other.
  • the notation such as "optionally substituted C 1 ⁇ C 6 haloalkylsulfonyl group by R 13" by any R 13 is a hydrogen atom bonded to a carbon atom, a substituted haloalkylsulfonyl group,
  • the number of R 13 to be substituted is arbitrarily selected within the range of each specified number of carbon atoms.
  • each R 13 may be the same as or different from each other.
  • [R 1 and R 2 may be bonded to each other to form a C 2 to C 6 alkylene bond, wherein the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom.
  • [R 9 and R 10 may combine with each other to form a C 2 -C 6 alkylene bond, wherein the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom.
  • [R 11 and R 12 may combine with each other to form a C 2 -C 6 alkylene bond, in which case the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom]
  • [R 12 and R 14 may be mutually bonded to form a C 2 -C 6 alkylene bond, in which case the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom], and the like.
  • alkylene bond and the heterocyclic ring formed by the atom adjacent to the alkylene bond include, for example, aziridine, azetidine, pyrrolidine, oxazolidine, oxazoline, isoxazoline, thiazolidine, imidazolidine, piperidine, morpholine, thiomorpholine, thiomorpholine- Examples include groups such as 1-oxide, thiomorpholine-1,1-dioxide, piperazine, homopiperidine or heptamethyleneimine.
  • [R 14 and R 15 may be mutually bonded to form a C 2 -C 6 alkylene bond, wherein the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom.
  • the heterocyclic ring formed by the alkylene bond and the atom adjacent to the alkylene bond such as 4,5-dihydroisoxazole, may be mentioned.
  • the notation such as [the C 2 -C 6 alkylene bond may be mono- or poly-substituted by a halogen atom or a C 1 -C 6 alkyl group] represents hydrogen bonded to a carbon atom constituting the alkylene bond.
  • atom represents a C 2 ⁇ C 6 alkylene linkage substituted by halogen atom or C 1 ⁇ C 6 alkyl group, the number of halogen atoms or C 1 ⁇ C 6 alkyl group is substituted, the substituent in the case of the mono-substituted Represents that any one of a halogen atom or a C 1 -C 6 alkyl group is substituted, and in the case of poly substitution, any one of two or more halogen atoms or a C 1 -C 6 alkyl group is substituted. Represents substitution. Also, when poly-substituted on the C 2 -C 6 alkylene bond (ie, when two or more substituents are present), each substituent may be the same as or different from each other.
  • agriculturally acceptable salts and salts refer to the compounds of the present invention represented by the general formula [I] when a hydroxyl group, a carboxyl group, an amino group or the like is present in the structure.
  • a salt with a metal or an organic base or a salt with a mineral acid or an organic acid examples of the metal include an alkali metal such as sodium or potassium or an alkaline earth metal such as magnesium or calcium; and an organic base such as triethylamine Or mineral acids such as hydrochloric acid, hydrobromic acid or sulfuric acid, and organic acids such as formic acid, acetic acid, methanesulfonic acid, 4-toluenesulfonic acid or Trifluoromethanesulfonic acid and the like can be mentioned.
  • Table 1 shows typical examples of compounds included in the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative of the present invention represented by the general formula [I].
  • Table 25 show typical examples of compounds included in the 3- (1H-1,2,4-triazol-1-yl) benzoic acid derivative of the present invention represented by the general formula [II].
  • 26 to Table 55 Table 56 to Table 58 show typical compound examples of the compounds included in the 1-phenyl-1H-1,2,4-triazole derivative of the present invention represented by the general formula [III]. Show. However, the compounds included in the derivative of the present invention are not limited to these.
  • the compound numbers in the table will be referred to in the following description.
  • the compound included in the phenyl-1H-1,2,4-triazole derivative may have an E-form or a Z-form geometric isomer depending on the type of the substituent. -Forms, Z-forms or mixtures containing E-forms and Z-forms in any proportion.
  • the compounds included in the present invention may have optical isomers due to the presence of one or more asymmetric carbon atoms and asymmetric sulfur atoms, but the present invention relates to all optically active compounds. , Racemates or diastereomers.
  • the compound of the present invention represented by the general formula [I] can be produced according to the following production methods, but is not limited to these methods.
  • the compound represented by the general formula [I-1] and “the compound [I-1]” are synonymous.
  • the compound represented by the general formula [I-1] can be produced, for example, using a compound represented by the general formula [III-1] according to a method comprising the following reaction formula. Can be.
  • Step 1-1 That is, the compound represented by the general formula [I-1] is obtained by converting the compound represented by the general formula [III-1] and the compound [IV-1] or the compound [IV-2] into an appropriate base. It can be produced by reacting in an appropriate solvent below.
  • the amount of compound [IV-1] or compound [IV-2] used in this step may be appropriately selected from the range of 1 mol to the amount of solvent relative to 1 mol of compound [III-1], and is preferably used. Is 1.0 to 2.0 mol.
  • Bases that can be used in this step include, for example, hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide and lithium hydroxide, hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide, Inorganic bases such as alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydrides such as sodium hydride and potassium hydride; sodium methoxy Metal salts of alcohols such as sodium, sodium ethoxide and potassium tert-butoxide, or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5,4,0 And organic bases such as -7-undecene.
  • alkali metals such as sodium hydroxide, potassium hydroxide and lithium hydroxide
  • alkaline earth metals such as calcium hydroxide and magnesium hydroxide
  • the amount of the base used may be appropriately selected from the range of 1 to 5 mol per 1 mol of the compound [III-1], and is preferably 1.0 to 3.0 mol.
  • the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone, methanol, ethanol , Alcohols such as 2-propanol, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, esters
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-1].
  • the reaction temperature in this step may be selected from an arbitrary temperature range from 0 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 150 ° C.
  • the reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 15 minutes to 24 hours.
  • compound [I-1] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., if necessary.
  • Step 1-2 The compound represented by the general formula [I-1] is obtained by reacting the compound represented by the general formula [III-1] with an aminating agent. And then reacting the compound [III-2] with the compound [IV-3] or the compound [IV-4] in the presence or absence of a suitable base, in the presence or absence of a suitable acid catalyst. In a suitable solvent.
  • the aminating agent that can be used in this step include ammonia, aqueous ammonia, and the like.
  • the amount of the aminating agent may be appropriately selected from the range of 1 to 30 mol per 1 mol of the compound [III-1], and is preferably 1.0 to 25.0 mol.
  • solvents such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane
  • aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene
  • Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like
  • Aprotic polar solvents alcohols such as methanol, ethanol and 2-propanol, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, esters such as ethyl acetate, pentane, hexane, cyclohe
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-1].
  • the reaction temperature in this step may be selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, and is preferably from ⁇ 10 ° C. to 100 ° C.
  • the reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 15 minutes to 24 hours.
  • compound [III-2] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [III-2] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • Step 1-3 The amount of compound [IV-3] or compound [IV-4] used in this step may be appropriately selected from the range of 1 mol to the amount of solvent relative to 1 mol of compound [III-2], and is preferably used. Is 1.0 to 10.0 mol. However, compound [IV-4] can also be used as the above solvent.
  • usable acid catalysts include, for example, sulfonic acids such as methanesulfonic acid or p-toluenesulfonic acid, mineral acids such as hydrochloric acid, hydrobromic acid or sulfuric acid, acetic acid or trifluoroacetic acid. And the like.
  • the amount of the acid catalyst used may be appropriately selected from the range of 0.01 mol to 10 mol per 1 mol of the compound [III-2], and is preferably 0.05 to 1.0 mol.
  • usable bases include, for example, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, and alkaline earth metals such as calcium hydroxide and magnesium hydroxide.
  • alkali metal carbonates such as sodium carbonate and potassium carbonate
  • inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate
  • metals such as sodium hydride and potassium hydride
  • Metal salts of alcohols such as hydrides, sodium methoxide, sodium ethoxide, potassium tert-butoxide, or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo Organic bases such as [5,4,0] -7-undecene.
  • the amount of the base used may be appropriately selected from the range of 1 mol to the amount of solvent relative to 1 mol of compound [III-2], and is preferably from 1.0 to 1.5 mol.
  • the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like
  • Aprotic polar solvents alcohols such as methanol, ethanol and 2-propanol, halogenated hydrocarbons such as dich
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-2].
  • the reaction temperature in this step may be selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, and is preferably from ⁇ 10 ° C. to 100 ° C.
  • the reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 15 minutes to 24 hours.
  • compound [I-1] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., if necessary.
  • the compound represented by the general formula [I-1] and the compound represented by the general formula [I-2] can be obtained by using, for example, a compound represented by the general formula [III-3]. It can be produced according to a method comprising the following reaction formula.
  • L 3 is a halogen atom, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkoxy group.
  • the compound represented by the general formula [I-1] includes the compound [IV-5], the compound [IV-6] derived from an acid halide and an acid anhydride, and the general formula [III-3].
  • the compound can be produced by reacting the compound represented with a suitable solvent in the presence or absence of a suitable acid in a suitable solvent.
  • the amount of compound [IV-6] used in this step may be appropriately selected from the range of 1 to 5 mol per 1 mol of compound [III-3], and is preferably 1.0 to 2.5 mol. It is.
  • examples of the acid that can be used include sulfonic acids such as methanesulfonic acid or p-toluenesulfonic acid, mineral acids such as hydrochloric acid, hydrobromic acid and sulfuric acid, and acetic acid and trifluoroacetic acid. And carboxylic acids.
  • the amount of the acid to be used may be appropriately selected from the range of 0.001 to 10 mol, preferably 0.001 to 3.0 mol, per 1 mol of compound [III-3].
  • solvents such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane
  • aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene
  • Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like
  • Aprotic polar solvents alcohols such as methanol, ethanol, 2-propanol, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and aliphatic carbons such as pentane, hexane, cyclohexane,
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-3].
  • the reaction temperature in this step may be selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, and is preferably from ⁇ 10 ° C. to 100 ° C.
  • the reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 10 minutes to 20 hours.
  • compound [I-1] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., if necessary.
  • the compound represented by the general formula [I-2] includes a compound [IV-7], a compound [IV-8] derived from carbon disulfide, an alkyl halide and the like, and a compound [IV-3].
  • the compound can be produced by reacting the compound represented with the compound in a suitable solvent.
  • the amount of compound [IV-8] used in this step may be appropriately selected from the range of 1 to 10 mol per 1 mol of compound [III-3], and is preferably 1.0 to 1.5 mol. It is.
  • the solvent that can be used in this step for example, the same solvent as described in Step 3 can be exemplified.
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-3].
  • the reaction temperature in this step may be selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, and is preferably from ⁇ 10 ° C. to 100 ° C.
  • the reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 10 minutes to 20 hours.
  • compound [I-2] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. Alternatively, compound [I-2] can also be isolated by concentrating the solvent from the reaction mixture. The isolated compound [I-2] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • the compound represented by the general formula [I-4], the compound represented by the general formula [I-5] and the compound represented by the general formula [I-6] include, for example, It can be produced using the compound represented by [I-3] according to a method comprising the following reaction formula.
  • R 3 , R 4 , R 6 , R 13 , R a , Z, p 1 and n have the same meaning as described above, M represents an alkali metal or an alkaline earth metal, and preferred alkali metals are can be exemplified sodium or potassium, substituted R 5a is C 1 ⁇ C 6 alkyl group, C 1 ⁇ C 6 haloalkyl group, C 1 ⁇ C 6 alkyl group optionally substituted by R 13, optionally by R 13 C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halo A cycloalkyl group, a phenyl group unsubstituted or substituted by (Z) p 1 , an aromatic heterocycle or a saturated heterocycle.) That is, the compound represented by the general
  • the amount of compound [IV-9] or compound [IV-10] used in this step may be appropriately selected from the range of 1 to 5 mol per 1 mol of compound [I-3], and is preferably 1 0.0 to 2.0 mol.
  • the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl
  • aprotic polar solvents such as sulfoxide, sulf
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [I-3].
  • the reaction temperature in this step may be selected from an arbitrary temperature range from ⁇ 70 ° C. to the reflux temperature in the reaction system, and is preferably from ⁇ 20 ° C. to 100 ° C.
  • the reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually from 10 minutes to 24 hours.
  • compound [I-4] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-4] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • Step 3-2 Examples of the copper halide that can be used in this step include copper (I) chloride, copper (I) bromide, copper (I) iodide, copper (II) chloride, copper (II) bromide, and the like. it can.
  • the amount of the copper halide to be used may be appropriately selected from the range of 0 to 5 mol per 1 mol of the compound [I-3], and is preferably 1.0 to 2.5 mol.
  • the solvent, reaction temperature, and reaction time that can be used in this step are the same as those in Step 3-1.
  • the reaction mixture is poured into water to neutralize, and then the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to obtain the compound [I-5].
  • the isolated compound [I-5] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • Step 3-3 Examples of the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, nitriles such as acetonitrile and propionitrile, and N, N-dimethyl.
  • ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, nitriles such as acetonitrile and propionitrile, and N, N-dimethyl.
  • Aprotic polar solvents such as formamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone, and a mixed solvent thereof; .
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-30 liters, per 1 mol of compound [I-3].
  • the reaction temperature and reaction time in this step are the same as in Step 3-1.
  • compound [I-6] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. Alternatively, compound [I-6] can be isolated by concentrating the solvent from the reaction mixture. The isolated compound [I-6] can be further purified by column chromatography, recrystallization, or the like, if necessary.
  • the compound represented by the general formula [I-8] can be produced, for example, using a compound represented by the general formula [I-7] according to a method comprising the following reaction formula. it can.
  • oxidizing agent examples include hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, oxone (OXONE, trade name of EI DuPont; products containing potassium hydrogen peroxosulfate), N -Chlorosuccinimide, N-bromosuccinimide, tert-butyl hypochlorite, sodium hypochlorite and the like.
  • the amount of the oxidizing agent depends on the oxidation number m of the sulfur atom of the compound represented by the general formula [I-8], but is in the range of 1 to 5 mol per 1 mol of the compound [I-7]. And it may be appropriately selected from the above, preferably from 1.0 to 2.5 mol.
  • Examples of the catalyst that can be used in this reaction include sodium tungstate.
  • the amount of the catalyst to be used may be appropriately selected from the range of 0.01 to 1 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound [I-7].
  • Solvents that can be used in this reaction include, for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide Aprotic polar solvents such as benzene, sulfolane, 1,3-dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol and 2-propanol; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane And aliphatic hydrocarbons such as pentane, hexane, cyclohexane and
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-15 liters, per 1 mol of compound [I-7].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range usually from ⁇ 30 ° C. to the reflux temperature in the reaction system, and is preferably from ⁇ 10 ° C. to 100 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually from 10 minutes to 24 hours.
  • the compound [I-8] can be isolated by pouring the reaction mixture into water or the like, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-8] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • the compound represented by the general formula [I-11] can be produced, for example, using a compound represented by the general formula [I-9] according to a method comprising the following reaction formula. it can.
  • R 3 , R 4 , R 6 , R a and n have the same meaning as described above, and R c represents a methyl group or a trifluoromethyl group.
  • the compound represented by the general formula [I-11] is produced by reacting the compound [I-9] with acetic anhydride or trifluoroacetic anhydride to produce the compound [I-10], and then producing the compound [I-11]. -10] in a suitable solvent in the presence of a suitable base or a suitable acid.
  • the amount of acetic anhydride or trifluoroacetic anhydride to be used in this reaction may be selected from the range of 1 mol to the amount of a solvent relative to 1 mol of compound [I-9], and is preferably from 1.0 to 7.0. 0 mol.
  • solvents such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane
  • aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene
  • Halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane
  • alcohols such as methanol, ethanol and 2-propanol
  • nitriles such as acetonitrile and propionitrile
  • esters such as ethyl acetate
  • pentane examples thereof include aliphatic hydrocarbons such as cyclohexane and heptane, water, and a mixed solvent thereof.
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [I-9].
  • usable bases include, for example, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metals such as calcium hydroxide and magnesium hydroxide.
  • inorganic bases such as alkali metal carbonates such as sodium carbonate and potassium carbonate, metal salts of alcohols such as sodium methoxide, sodium ethoxide and potassium tert-butoxide or triethylamine, N, N-dimethyl Organic bases such as aniline, pyridine, 4-N, N-dimethylaminopyridine, and 1,8-diazabicyclo [5.4.0] -7-undecene.
  • the amount of the base to be used may be appropriately selected from the range of 1 to 10 mol per 1 mol of compound [I-9], and is preferably 1.0 to 5.0 mol.
  • usable acids include, for example, mineral acids such as hydrochloric acid, hydrobromic acid and sulfuric acid, and carboxylic acids such as acetic acid and trifluoroacetic acid.
  • the amount of the acid to be used may be appropriately selected from the range of 1 to the amount of the solvent per 1 mol of the compound [I-9], and is preferably 1 to 100 mol.
  • the reaction temperature of this reaction may be selected from any temperature range from ⁇ 10 ° C. to the reflux temperature in the reaction system in any reaction, and is preferably performed in a temperature range of 0 ° C. to 50 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like in each reaction, but is usually 5 minutes to 24 hours.
  • compound [I-11] can be isolated by pouring the reaction mixture into water or the like, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-11] can be further purified by column chromatography, recrystallization, and the like, if necessary. In addition, compound [I-11] can be used for the next reaction (Production method 6) without isolation and purification.
  • the compound represented by the general formula [I-12] can be produced, for example, using a compound represented by the general formula [III-3] according to a method comprising the following reaction formula. Can be.
  • R 3 , R 4 , R 6 , R a , R b , L 1 , A and n have the same meaning as described above.
  • Step 6-1 That is, the compound represented by the general formula [I-12] is prepared by combining the compound represented by the general formula [III-3] with a cyanate or thiocyanate in a suitable solvent in the presence of a suitable acid. And converting the compound [III-4] to the compound [IV-3] or the compound [IV-4] in the presence of a suitable base. Alternatively, it can be produced by reacting in a suitable solvent in the presence of a suitable acid catalyst. Examples of the cyanate or thiocyanate that can be used in this reaction include sodium cyanate, potassium cyanate, ammonium cyanate, sodium thiocyanate, potassium thiocyanate, and ammonium thiocyanate.
  • the amount of the cyanate or thiocyanate to be used may be selected from the range of 1 mol to 10 mol per 1 mol of the compound [III-3], and is preferably 1.0 to 6.0 mol.
  • Examples of the acid that can be used in this step include mineral acids such as hydrochloric acid and hydrobromic acid.
  • the amount of the acid used may be appropriately selected from the range of 1 to the amount of the solvent based on 1 mol of the compound [III-4], and is preferably from 1.0 to 10.0 mol.
  • Examples of the solvent that can be used in this step include nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, Examples include aprotic polar solvents such as 3-dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol and 2-propanol, water or a mixed solvent thereof.
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-3].
  • the reaction temperature in this step may be selected from an arbitrary temperature range from ⁇ 30 ° C.
  • reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 10 minutes to 20 hours.
  • compound [I-12] can be isolated by performing an operation such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-12] can be further purified by column chromatography, recrystallization or the like, if necessary.
  • Step 6-2 The compound represented by the general formula [I-12] is produced by reacting the compound represented by the general formula [III-4] under the same conditions as in step 1-3 of production method 1. Can be.
  • the compound represented by the general formula [I-14] can be produced, for example, using a compound represented by the general formula [I-13] according to a method comprising the following reaction formula. Can be.
  • the amount of compound [IV-11] or compound [IV-12] used in this reaction may be appropriately selected from the range of 1 to 20 mol per 1 mol of compound [I-13], and is preferably 1 0.1 to 5.5 mol.
  • Bases that can be used in this reaction include, for example, hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide and lithium hydroxide, hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide, Inorganic bases such as alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, metal hydrides such as sodium hydride and potassium hydride, sodium methoxide , Sodium ethoxide, potassium tert-butoxide and other metal salts of alcohols or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0
  • the amount of the base used may be appropriately selected from the range of 1 to 5 mol per 1 mol of the compound [I-13], and is preferably 1.0 to 2.0 mol.
  • organic bases such as triethylamine and pyridine can also be used as the solvent.
  • the radical initiator that can be used in this reaction include sulfurous acid, a sulfite, and a sulfurous acid adduct such as Rongalite (trade name, sodium formaldehyde sulfoxylate).
  • the amount of the radical initiator to be used may be appropriately selected from the range of 0.01 to 5 mol per 1 mol of the compound [I-13], and is preferably 0.01 to 1.2 mol.
  • solvents such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane
  • aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene
  • Halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl Aprotic polar solvents such as sulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol, 2-propanol, esters such as ethyl acetate, pentane, hexane, cyclo
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [I-13].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 150 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 10 minutes to 20 hours.
  • compound [I-14] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-14] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • the compound represented by the general formula [I-15], the compound represented by the general formula [I-16] and the compound represented by the general formula [I-17] include, for example, It can be produced using the compound represented by [I-2] according to a method comprising the following reaction formula.
  • R 3 , R 4 , R 5 , R a , M, L 1 and n have the same meanings as described above, and R 6a is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, Represents a 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group or a C 3 -C 6 cycloalkyl group.
  • Step 8-1) That is, the compound represented by the general formula [I-15] is produced by reacting the compound represented by the general formula [I-2] under the same conditions as in step 3-1 of the production method 3. can do.
  • Step 8-2 The compound represented by the general formula [I-16] is produced by reacting the compound represented by the general formula [I-2] under the same conditions as in step 3-2 of the production method 3. can do.
  • Step 8-3 Further, the compound represented by the general formula [I-17] is produced by reacting the compound represented by the general formula [I-2] under the same conditions as in Step 3-3 of Production Method 3. can do.
  • the compound represented by the general formula [I-1] can be produced, for example, using a compound represented by the general formula [I-2] according to a method comprising the following reaction formula. Can be.
  • the compound represented by the general formula [I-1] is prepared by combining the compound represented by the general formula [I-2] with a suitable electrophilic reagent in the presence or absence of a suitable solvent. It can be produced by reacting in the presence or absence of a base, in the presence or absence of a suitable acid, in the presence or absence of a suitable dehydrating condensing agent.
  • the amount of the electrophilic reagent used in this reaction may be appropriately selected from the range of 1 to the amount of the solvent, and preferably 1 to 150 mol, per 1 mol of compound [I-2].
  • usable bases include, for example, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, and alkaline earth metals such as calcium hydroxide and magnesium hydroxide.
  • Metal salts of alcohols such as hydrides, sodium methoxide, sodium ethoxide, potassium tert-butoxide or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [ Organic bases such as [5,4,0] -7-undecene.
  • the amount of the base used may be appropriately selected from the range of 0.01 to 5 mol, and preferably 0.1 to 3.0 mol, per 1 mol of compound [I-2]. It is.
  • the acid that can be used is a Lewis acid, for example, sulfonic acids such as methanesulfonic acid or p-toluenesulfonic acid, mineral acids such as hydrochloric acid, hydrobromic acid or sulfuric acid, and acetic acid. Or carboxylic acids such as trifluoroacetic acid.
  • the amount of the acid used may be appropriately selected from the range of 0.001 to 5 mol per 1 mol of the compound [I-2], and is preferably 0.01 to 2.0 mol.
  • examples of the dehydration condensing agent that can be used include N, N′-dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1-ethyl- 3- (3-dimethylaminopropyl) carbodiimide, O- (benzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate, 4- (4 Examples thereof include 6-dimethoxy-1,3,5-triazin-2-yl) -4-methylmorpholinium chloride, 1-hydroxybenzotriazole, and a mixture thereof.
  • the amount of the dehydrating condensing agent to be used may be appropriately selected from the range of 1 to 3 mol per 1 mol of compound [I-2], and is preferably 1.0 to 1.2 mol, respectively.
  • the solvent that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like Aprotic polar solvents, alcohols such as methanol, ethanol, 2-propanol, halogenated
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-20 liters, per 1 mol of compound [I-2].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 20 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 150 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 15 minutes to 24 hours.
  • compound [I-1] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., if necessary.
  • the compound represented by the general formula [I-1] can be produced, for example, using a compound represented by the general formula [I-18] according to a method comprising the following reaction formula. Can be.
  • the compound of the present invention represented by the general formula [I-1] can be prepared by converting the compound represented by the general formula [I-18] and the compound [IV-15] in the presence or absence of a suitable base. In a suitable solvent.
  • the amount of compound [IV-15] used in this reaction may be appropriately selected from the range of 1 to the amount of solvent relative to 1 mol of compound [I-18], and is preferably 1.0 to 10.0. Is a mole.
  • usable bases include, for example, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, and alkaline earth metals such as calcium hydroxide and magnesium hydroxide.
  • alkali metal carbonates such as sodium carbonate and potassium carbonate
  • inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate
  • metals such as sodium hydride and potassium hydride
  • Metal salts of alcohols such as hydrides, sodium methoxide, sodium ethoxide, potassium tert-butoxide or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [ Organic bases such as [5,4,0] -7-undecene.
  • the amount of the base to be used may be appropriately selected from the range of 1 to 10 mol per 1 mol of compound [I-18], and is preferably 1.0 to 3.0 mol.
  • the solvent that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like
  • Aprotic polar solvents alcohols such as methanol, ethanol, 2-propanol, halogenated hydrocarbons such as dichlorome
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-20 liters, per 1 mol of compound [I-18].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 20 ° C. to the reflux temperature in the reaction system, and is preferably from ⁇ 10 ° C. to 150 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 15 minutes to 20 hours.
  • compound [I-1] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., if necessary.
  • the compound represented by the general formula [I-1] can be produced, for example, using a compound represented by the general formula [IV-16] according to a method comprising the following reaction formula. Can be.
  • L 6 represents a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a nonafluorobutanesulfonyloxy A benzenesulfonyloxy group, a p-toluenesulfonyloxy group, a dimethylsulfamoyloxy group, a dihydroxyboryl group (B (OH) 2 ), or a pinacolatoboran-2-yl group.
  • the compound represented by the general formula [I-1] is obtained by converting the compound [IV-16] and the compound [IV-17] into International Patent Publication WO2006 / 043635 or European Patent Publication EP30022279.
  • the compound represented by the general formula [II-2] can be produced, for example, using a compound represented by the general formula [III-4] according to a method comprising the following reaction formula. Can be.
  • the compound represented by the general formula [II-2] can be obtained by cyanating the compound represented by the general formula [III-5] in a suitable solvent in the presence or absence of a suitable catalyst, in a suitable solvent. It can be produced by subjecting the compound represented by [III-6] to a hydrolysis reaction in a suitable solvent in the presence of a suitable acid or base.
  • Step 12-1 Examples of the cyan compound used in this step include sodium cyanide, potassium cyanide, ammonium cyanide, zinc cyanide, copper cyanide, and mixtures thereof.
  • the amount of the cyan compound to be used may be appropriately selected usually from the range of 1 to 100 mol per 1 mol of the compound [III-5], and is preferably 1.0 to 5.0 mol.
  • Examples of the catalyst used in this step include tetrakis (triphenylphosphine) palladium.
  • the amount of the catalyst to be used may be appropriately selected usually from the range of 0.001 to 0.5 mol per 1 mol of the compound [III-5], and is preferably from 0.01 to 0.1 mol.
  • solvents such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane
  • aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene
  • dichloromethane examples include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane.
  • Chloroform halogenated hydrocarbons such as 1,2-dichloroethane, etc., nitriles such as acetonitrile, propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , Sulfolane, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol and 2-propanol, esters such as ethyl acetate, pentane, hexane and cyclohexa , Aliphatic hydrocarbons such as heptane, pyridine, pyridine picoline, etc., can be mentioned water, or a mixed solvent thereof, or the like.
  • the amount of the solvent to be used is 0.1 to 500 liter, preferably 0.3 to 50 liter, per 1 mol of compound [III-5].
  • the reaction temperature in this step may be selected from an arbitrary temperature range from usually ⁇ 30 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 150 ° C.
  • the reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually from 10 minutes to 72 hours.
  • compound [III-6] is isolated by performing operations such as pouring the reaction mixture into water, and collecting the precipitated solid by filtration or extraction with an organic solvent and then concentration. be able to.
  • the isolated compound [III-6] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • Step 12-2 Examples of the acid that can be used in this step include mineral acids such as hydrochloric acid, hydrobromic acid and sulfuric acid, carboxylic acids such as acetic acid and trifluoroacetic acid, and sulfonic acids such as methanesulfonic acid and trifluoromethanesulfonic acid.
  • the amount of the acid to be used may be appropriately selected from the range of 1 to the equivalent of the amount of the solvent per 1 mol of the compound [III-6], and is preferably 1.0 to 100.0 mol.
  • Examples of the base that can be used in this step include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydrogen carbonate; And inorganic bases such as alkali metal bicarbonates such as potassium hydrogen.
  • the amount of the base used may be appropriately selected from the range of 0.1 to 50 mol per 1 mol of compound [III-6], and is preferably 0.5 to 20.0 mol.
  • Examples of the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like
  • Examples include aprotic polar solvents, alcohols such as methanol, ethanol and 2-propanol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, water, and mixed solvents thereof.
  • the amount of the solvent to be used is 0.1-500 liter, preferably 0.3-30 liter, per 1 mol of compound [III-6].
  • the reaction temperature in this step may be selected from an arbitrary temperature range from usually ⁇ 30 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 150 ° C.
  • the reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually from 10 minutes to 72 hours.
  • the reaction mixture is poured into water for neutralization, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to obtain the compound [II-2]. Can be isolated.
  • the isolated compound [II-2] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • Step 12-3 The compound represented by the general formula [II-2] is described in J. Am. Organometal. Chem. 358, pp. 563 to 565 (1988) or by a CO insertion reaction using a transition metal catalyst such as palladium according to the method.
  • the compound represented by the general formula [II-2] is described in Chem. Rev .. 90, pages 879 to 933 (1990), or lithiated and then reacted with carbon dioxide gas according to the method.
  • Step 12-4 the compound represented by the general formula [II-2] is described in J. Am. Org. Chem. 39, pp. 3318-3326 (1974), or by a CO insertion reaction using a transition metal catalyst such as palladium according to the method described above, to obtain a compound represented by the general formula [II-1]. And then subjecting the compound to a hydrolysis reaction in a suitable solvent in the presence of a suitable acid or base.
  • Step 12-5 The acid, base, solvent, reaction temperature and reaction time that can be used in this step are the same as in Step 12-2. After completion of the reaction, the reaction mixture is poured into water for neutralization, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to obtain the compound [II-2]. Can be isolated. The isolated compound [II-2] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • the compound represented by the general formula [I-19] can be produced, for example, using a compound represented by the general formula [II-2] according to a method comprising the following reaction formula. Can be.
  • Step 13-1) That is, the compound represented by the general formula [I-19] can be obtained by converting the compound represented by the general formula [II-2] and the compound [IV-18] in the presence of a suitable dehydrating condensing agent and a suitable base. Alternatively, it can be produced by reacting in a suitable solvent in the absence.
  • the amount of compound [IV-18] used in this step may be appropriately selected from the range of 1 to 10 mol per 1 mol of compound [II-2], and is preferably 1.0 to 5.0 mol. It is.
  • the dehydrating condensing agent that can be used in this step includes, for example, N, N′-dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1-ethyl-3- (3-dimethylaminopropyl) Carbodiimide, O- (benzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate, 4- (4,6-dimethoxy-1,3,5 -Triazin-2-yl) -4-methylmorpholinium chloride, 1-hydroxybenzotriazole or a mixture thereof.
  • the amount of the dehydrating condensing agent may be appropriately selected from the range of 1 to 5 moles per 1 mole of the compound [II-2], and is preferably 1.0 to 3.0 moles.
  • usable bases include, for example, triethylamine, 4-methylmorpholine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] -7-undecene, pyridine, 4-N , N-dimethylaminopyridine, and organic bases such as 2,6-lutidine.
  • the amount of the base used may be appropriately selected from the range of 0.1 to 5 mol per 1 mol of compound [II-2], and is preferably 0.1 to 3.0 mol.
  • Examples of the solvent that can be used in this step include halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; esters such as ethyl acetate; Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone Aprotic polar solvents, such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and the like; and mixed solvents thereof.
  • halogenated hydrocarbons such as dichloromethane, chloroform,
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-50 liters, per 1 mol of compound [II-2].
  • This step can be performed in the presence of a catalyst, if necessary, and the catalyst can be appropriately selected from 4-N, N-dimethylaminopyridine and the like.
  • the amount of the catalyst used may be appropriately selected from the range of 0.001 to 1 mol per 1 mol of the compound [II-2], and is preferably 0.01 to 0.1 mol.
  • the reaction temperature in this step may be selected from an arbitrary temperature range from ⁇ 20 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 80 ° C.
  • reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 1 minute to 100 hours.
  • compound [I-19] can be isolated by performing an operation such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture.
  • the isolated compound [I-19] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • the compound of the present invention represented by the general formula [I-19] can be prepared by converting the compound represented by the general formula [II-2] in an appropriate solvent in the presence or absence of an appropriate catalyst in an appropriate solvent.
  • the compound is converted to a compound [II-3] which is an active derivative such as a halide or a mixed acid anhydride, and then reacted with a compound [IV-18] in a suitable solvent in the presence of a suitable base.
  • thionyl chloride or oxalyl chloride can be used.
  • a reagent to be converted into another active derivative isobutyl chlorocarbonate, methanesulfonyl chloride, trifluoromethanesulfonyl chloride, p-toluenesulfonyl chloride and the like can be used.
  • the amount of the reagent to be converted into the active derivative may be appropriately selected from the range of 0.5 to 5 mol per 1 mol of the compound [II-2], and is preferably 0.5 to 2.2 mol. is there.
  • usable catalysts include, for example, N, N-dimethylformamide and the like.
  • the amount of the catalyst to be used may be appropriately selected from the range of 0.01 to 1 mol per 1 mol of the compound [II-2], and is preferably 0.01 to 0.3 mol.
  • the solvent that can be used in this step include halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, pentane, hexane, cyclohexane and heptane.
  • Such as aliphatic hydrocarbons such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3 Aprotic polar solvents such as -dimethyl-2-imidazolidinone; ethers such as diethyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; and mixed solvents thereof. It can.
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [II-2].
  • the reaction temperature in this step may be selected from an arbitrary temperature range from ⁇ 20 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 80 ° C.
  • the reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually from 1 minute to 48 hours.
  • compound [II-3] can be isolated by performing an operation such as concentration.
  • Step 13-3 Production of compound [I-19] by reacting compound [IV-18] with the obtained reaction solution containing compound [II-3] in the presence of a suitable base and in a suitable solvent.
  • the amount of compound [IV-18] used in this step may be appropriately selected from the range of 1 to 3 mol per 1 mol of compound [II-2], and is preferably 1.0 to 2.5 mol. It is.
  • Bases that can be used in this step include, for example, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, and lithium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, sodium hydrogen carbonate, and hydrogen carbonate.
  • Inorganic bases such as bicarbonates of alkali metals such as potassium, metal hydrides such as sodium hydride and potassium hydride or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine; Organic bases such as 1,8-diazabicyclo [5,4,0] -7-undecene are exemplified.
  • the amount of the base used may be appropriately selected from the range of 1 to 5 mol per 1 mol of the compound [II-2], and is preferably 1.0 to 2.5 mol.
  • solvent examples include halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene, pentane, hexane, cyclohexane, and heptane.
  • halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane
  • aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene
  • pentane hexane
  • cyclohexane cyclohexane
  • heptane examples include heptane.
  • Such as aliphatic hydrocarbons such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3 Aprotic polar solvents such as -dimethyl-2-imidazolidinone, ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; water; and mixed solvents thereof. be able to.
  • aliphatic hydrocarbons such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3 Aprotic polar solvents such as -dimethyl-2-imidazolidinone, ether
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [II-2].
  • the reaction temperature in this step may be selected from an arbitrary temperature range from ⁇ 20 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 80 ° C.
  • the reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually from 1 minute to 48 hours.
  • compound [I-19] can be isolated by performing an operation such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture.
  • the isolated compound [I-19] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • the compound represented by the general formula [I] can be produced, for example, using a compound represented by the general formula [I-20] according to a method comprising the following reaction formula. .
  • L 8 represents a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, And a nonafluorobutanesulfonyloxy group, a benzenesulfonyloxy group, a p-toluenesulfonyloxy group, and the like.
  • the compound of the present invention represented by the general formula [I] can be obtained by converting the compound represented by the general formula [I-20] and the compound [IV-19] in the presence or absence of a suitable base.
  • the amount of compound [IV-19] to be used in this reaction may be appropriately selected from the range of 1 to 100 mol per 1 mol of compound [I-20], and is preferably 1.0 to 10.0 mol. It is.
  • usable bases include, for example, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, and alkaline earth metals such as calcium hydroxide and magnesium hydroxide.
  • alkali metal carbonates such as sodium carbonate and potassium carbonate
  • inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate
  • metals such as sodium hydride and potassium hydride
  • Metal salts of alcohols such as hydrides, sodium methoxide, sodium ethoxide, potassium tert-butoxide or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [ Organic bases such as [5,4,0] -7-undecene.
  • the amount of the base to be used may be appropriately selected from the range of 1 to 10 mol per 1 mol of compound [I-20], and is preferably 1.0 to 5.0 mol.
  • the solvent that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Esters such as ethyl acetate, nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl- Aprotic polar solvents such as 2-imidazolidinone, alcohols such as methanol, ethanol and 2-propanol
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-20 liters, per 1 mol of compound [I-20].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 20 ° C. to the reflux temperature in the reaction system, and is preferably from ⁇ 10 ° C. to 80 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 15 minutes to 48 hours.
  • the compound [I] can be isolated by pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I] can be further purified by column chromatography, recrystallization or the like, if necessary.
  • the compound represented by the general formula [I-21] can be produced, for example, using a compound represented by the general formula [I-19] according to a method comprising the following reaction formula. Can be.
  • the compound represented by the general formula [I-21] can be prepared by combining the compound represented by the general formula [I-19] with a suitable thiocarbonylating agent in the presence or absence of a suitable base. It can be produced by reacting in the presence or absence of a suitable solvent.
  • the thiocarbonylating agent used in this reaction is diphosphorus pentasulfide or Lawesson's Reagent (2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane- 2,4-disulfide) and the like.
  • the amount of the thiocarbonylating agent to be used may be appropriately selected from the range of 0.5 to 100 mol, preferably 0.5 to 3.0 mol, per 1 mol of compound [I-19].
  • Addition of a base is not always necessary in this reaction, but when a base is used, examples of the usable base include inorganic bases such as alkali metal carbonates such as sodium carbonate and potassium carbonate, and triethylamine, N, N- Organic bases such as dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, and 1,8-diazabicyclo [5,4,0] -7-undecene are exemplified.
  • the amount of the base to be used may be appropriately selected from the range of 0.01 to 10 mol, and preferably 0.1 to 2.0 mol, per 1 mol of compound [I-19].
  • the solvent that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Aprotic polar solvents such as dimethyl sulfoxide and sulfolane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane, or mixed solvents thereof Is mentioned.
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-15 liters, per 1 mol of compound [I-19].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from 0 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 150 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 15 minutes to 48 hours.
  • compound [I-19] can be isolated by performing an operation such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture.
  • the isolated compound [I-19] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • the compound represented by the general formula [III-3] can be produced, for example, using a compound represented by the general formula [III-7] according to a method comprising the following reaction formula.
  • Step 1'-1 That is, the compound represented by the general formula [III-8] is represented by the general formula [III-7] in accordance with “Reduced general term” in Vol. By reducing the nitro compound.
  • the compound [III-7] generally available reagents can be used, and the compound [III-7] can also be produced by a method described in International Publication WO2009 / 078481 or a method similar thereto.
  • Step 1'-2 The compound represented by the general formula [III-3] is prepared by reacting the compound represented by the general formula [III-8] with a nitrite in a suitable solvent in the presence of a suitable mineral acid. After being converted to a salt, it can be produced by reducing it with a metal reducing reagent such as zinc dust, sodium sulfite, tin chloride or the like.
  • Mineral acids that can be used in this step include hydrochloric acid, sulfuric acid and the like.
  • the amount of the mineral acid to be used may be appropriately selected from the range of 2 to 10 mol per 1 mol of the compound [III-8], and is preferably 2.0 to 5.0 mol.
  • the amount of the nitrite used in this step may be appropriately selected from the range of 1 to 5 mol per 1 mol of the compound [III-8], and is preferably 1.0 to 1.2 mol.
  • the amount of the metal reducing reagent that can be used in this step may be appropriately selected from the range of 1 to 20 mol per 1 mol of compound [III-8], and is preferably 1.0 to 5.0 mol.
  • Examples of the solvent that can be used in this step include water, hydrochloric acid, sulfuric acid, acetic acid, a mixed solvent thereof, and the like.
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-8].
  • the reaction temperature in this step may be selected from an arbitrary temperature range from ⁇ 20 ° C. to the reflux temperature in the reaction system, and is preferably from ⁇ 5 ° C. to 20 ° C.
  • the reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 30 minutes to 5 hours.
  • compound [III-3] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [III-3] can be further purified by column chromatography, recrystallization, and the like, if necessary.
  • the compound represented by the general formula [III-1] can be produced, for example, using a compound represented by the general formula [III-3] according to a method comprising the following reaction formula.
  • Step 2'-1 That is, the compound represented by the general formula [III-1] is obtained by converting the compound represented by the general formula [III-3] and the compound [IV-20] or the compound [IV-21] to a suitable acid catalyst.
  • the compound represented by the general formula [III-9] can be produced by reacting in a suitable solvent in the presence or absence of the compound, and then reacting with a halogenating agent.
  • the amount of compound [IV-20] or compound [IV-21] used in this step may be appropriately selected from the range of 1 to 5 mol per 1 mol of compound [III-3], and is preferably 1 0.0 to 1.2 mol.
  • Examples of the acid catalyst that can be used in this step include sulfonic acids such as methanesulfonic acid and p-toluenesulfonic acid, and Lewis acids such as titanium tetrachloride.
  • the amount of the acid catalyst to be used may be appropriately selected from the range of 0.001 to 5 mol, and preferably 0.01 to 1.2 mol, per 1 mol of compound [III-3].
  • solvents such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane
  • aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene
  • Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like
  • Aprotic polar solvents alcohols such as methanol, ethanol, 2-propanol isopropyl alcohol, aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane, pyridines such as pyridine and picoline, or a
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-3].
  • Examples of the halogenating agent used in this step include chlorine, N-chlorosuccinimide, N-bromosuccinimide, tert-butyl hypochlorite and the like.
  • the amount of the halogenating agent to be used may be appropriately selected from the range of 1 to 5 mol per 1 mol of the compound [III-9], and is preferably 1.0 to 1.1 mol.
  • the reaction temperature in this step may be selected from an arbitrary temperature range from ⁇ 70 ° C. to the reflux temperature in the reaction system, and is preferably from ⁇ 20 ° C. to 100 ° C.
  • reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 15 minutes to 24 hours.
  • compound [III-1] can be isolated by performing operations such as pouring the reaction mixture into water, extracting with an organic solvent, and then concentrating the mixture. The isolated compound [III-1] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • the compound represented by the general formula [III-1] can be prepared by converting the compound represented by the general formula [III-3] and the compound [IV-22] in the presence or absence of a suitable base.
  • the compound represented by the general formula [III-10] can be produced by reacting with a suitable solvent and then reacting with a halogenating agent.
  • the amount of compound [IV-22] used in this step may be appropriately selected from the range of 1 to 15 mol per 1 mol of compound [III-3], and is preferably 1.0 to 7.0 mol. It is.
  • Bases that can be used in this step include, for example, hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide and lithium hydroxide, hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide, Inorganic bases such as alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydrides such as sodium hydride and potassium hydride; sodium methoxy Metal salts of alcohols such as sodium, sodium ethoxide and potassium tert-butoxide, or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5,4,0 And organic bases such as -7-undecene.
  • alkali metals such as sodium hydroxide, potassium hydroxide and lithium hydroxide
  • alkaline earth metals such as calcium hydroxide and magnesium hydroxide
  • the amount of the base used may be appropriately selected from the range of 1 to 10 mol per 1 mol of compound [III-3], and is preferably 1.0 to 1.2 mol.
  • the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like
  • Aprotic polar solvents alcohols such as methanol, ethanol and 2-propanol, halogenated hydrocarbons such as dichloromethane
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-3].
  • the halogenating agent that can be used in this step include phosphorus trichloride, phosphorus tribromide, thionyl chloride, phosphorus oxychloride, phosphorus pentachloride, triphenylphosphine / carbon tetrachloride, or triphenylphosphine / carbon tetrabromide.
  • the amount of the halogenating agent to be used may be appropriately selected from the range of 1 mol to the amount of the solvent relative to 1 mol of compound [III-10], and is preferably 1.0 to 5.0 mol.
  • the reaction temperature in this step may be selected from an arbitrary temperature range from ⁇ 70 ° C. to the reflux temperature in the reaction system, and is preferably from ⁇ 20 ° C. to 100 ° C.
  • the reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 15 minutes to 24 hours.
  • compound [III-1] can be isolated by performing operations such as pouring the reaction mixture into water, extracting with an organic solvent, and then concentrating the mixture. Alternatively, compound [III-1] can also be isolated by concentrating the solvent from the reaction mixture. The isolated compound [III-1] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • the compound represented by the general formula [III-5] can be produced, for example, using a compound represented by the general formula [III-11] according to a method comprising the following reaction formula.
  • the compound represented by the general formula [III-5] can be produced by reacting the compound represented by the general formula [III-11] with a halogenating agent in a suitable solvent.
  • Halogenating agents usable in this reaction include chlorine, sulfuryl chloride, N-chlorosuccinimide, bromine, N-bromosuccinimide, 1,3-dibromo-5,5-hydantoin, iodine, N-iodosuccinimide, 1,3-diiodo-5,5-hydantoin and the like can be mentioned.
  • the amount of the halogenating agent to be used may be appropriately selected from the range of 0.5 to 10 mol, preferably 0.5 to 2.0 mol, per 1 mol of compound [III-11].
  • the solvent that can be used in this reaction include halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; acetonitrile, propionitrile; Aprotic polar solvents such as nitriles, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone;
  • carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid, sulfuric acid, water, and a mixed solvent thereof.
  • the amount of the solvent to be used is 0.1-300 liter, preferably 0.3-20 liter, per 1 mol of compound [III-11].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from -70 ° C to the reflux temperature in the reaction system, and is preferably from -20 ° C to 100 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually from 10 minutes to 24 hours.
  • the compound [III-5] is isolated by performing operations such as pouring the reaction mixture into water, and collecting the precipitated solid by filtration or extraction with an organic solvent and concentration. be able to.
  • the isolated compound [III-5] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • the 3- (1H-1,2,4-triazol-1-yl) benzoic acid derivative represented by the general formula [II] of the present invention or an ester thereof is represented by the general formula [I] of the present invention.
  • the 1-phenyl-1H-1,2,4-triazole derivative represented by the general formula [III] of the present invention is a 3- (1H-1,2) represented by the general formula [II] of the present invention.
  • the pesticidal composition of the present invention comprises a 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative represented by the general formula [I] of the present invention or an agriculturally acceptable salt thereof. Contains as an active ingredient.
  • the pesticidal composition of the present invention can contain, if necessary, additional components (carriers) usually used in pesticide preparations.
  • the pest control agent of the present invention is a 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative represented by the general formula [I] of the present invention or an agriculturally acceptable salt thereof.
  • the pesticides of the present invention are typically insecticides, acaricides and nematocides.
  • the pest control agent of the present invention can contain, as necessary, an additive component (carrier) usually used in agricultural chemical formulations.
  • a carrier such as a solid carrier or a liquid carrier, a surfactant, a binder or a tackifier, a thickener, a coloring agent, a spreading agent, a spreading agent, an antifreezing agent, an anti-caking agent, Disintegrators, decomposition inhibitors and the like can be mentioned, and if necessary, preservatives, plant fragments and the like may be used as additional components.
  • a carrier such as a solid carrier or a liquid carrier, a surfactant, a binder or a tackifier, a thickener, a coloring agent, a spreading agent, a spreading agent, an antifreezing agent, an anti-caking agent, Disintegrators, decomposition inhibitors and the like can be mentioned, and if necessary, preservatives, plant fragments and the like may be used as additional components.
  • These additional components may be used alone or in combination of two or more.
  • Solid carriers include, for example, pyrophyllite clay, kaolin clay, silica clay, talc, diatomaceous earth, zeolite, bentonite, acid clay, activated clay, attapulgase clay, vermiculite, perlite, pumice, white carbon (synthetic silicic acid, Mineral carriers such as synthetic silicates) and titanium dioxide; vegetable carriers such as wood flour, corn stalk, walnut shell, fruit nucleus, peach, sawdust, bran, soy flour, powdered cellulose, starch, dextrin, saccharides and the like; Inorganic salt carriers such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride; and polymer carriers such as polyethylene, polypropylene, polyvinyl chloride, polyvinyl acetate, ethylene-vinyl acetate copolymer, and urea-aldehyde resins. it can.
  • liquid carrier examples include monohydric alcohols such as methanol, ethanol, propanol, 2-propanol, butanol, and cyclohexanol; and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • monohydric alcohols such as methanol, ethanol, propanol, 2-propanol, butanol, and cyclohexanol
  • polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • Polyhydric alcohol derivatives such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone and isophorone; ethyl ether, 1,4-dioxane, cellosolve, dipropyl ether; Ethers such as tetrahydrofuran; aliphatic hydrocarbons such as normal paraffin, naphthene, isoparaffin, kerosene and mineral oil; , C 9 -C 10 alkylbenzene, xylene, solvent naphtha, alkylnaphthalene, aromatic hydrocarbons such as high-boiling aromatic hydrocarbons; 1,2-dichloroethane, chloroform, halogenated hydrocarbons such as carbon tetrachloride, acetic acid Esters such as ethyl, diisopropyl phthalate,
  • the surfactant is not particularly limited, but is preferably one that gels in water or exhibits swelling properties, for example, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene Fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene poly Oxypropylene block polymer, alkyl polyoxyethylene polypropylene block polymer ether, polyoxyethylene alkylamine, polyoxyethylene Fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol, polyoxyalkylene-added acetylene dio
  • binder and tackifier examples include carboxymethylcellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6,000 to Examples include polyethylene glycol having a molecular weight of 20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, and natural phospholipids (eg, cephalic acid, lecithin, etc.).
  • carboxymethylcellulose and salts thereof examples include carboxymethylcellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6,000 to Examples include polyethylene glycol having a molecular weight of 20,000, polyethylene oxide having
  • thickener examples include water-soluble polymers such as xanthan gum, guar gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch derivative, and polysaccharide; inorganic fine powders such as high-purity bentonite and white carbon And the like.
  • coloring agent examples include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue; and organic dyes such as alizarin dye, azo dye, and metal phthalocyanine dye.
  • the spreading agent examples include silicone surfactants, cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, cross-linked polyvinyl pyrrolidone, maleic acid and styrenes, methacrylic acid copolymers, and polymers of polyhydric alcohols. And a diester of a dicarboxylic acid, and a water-soluble salt of polystyrenesulfonic acid.
  • the spreading agent examples include various surfactants such as sodium dialkyl sulfosuccinate, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, and polyoxyethylene fatty acid ester; paraffin, terpene, polyamide resin, polyacrylate , Polyoxyethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, synthetic resin emulsion and the like.
  • antifreeze examples include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
  • anti-caking agent examples include polysaccharides such as starch, alginic acid, mannose and galactose; polyvinylpyrrolidone, white carbon, ester gum, petroleum resin and the like.
  • disintegrating agent examples include sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, a copolymer of methacrylic acid ester, polyvinylpyrrolidone, a polyaminocarboxylic acid chelate compound, and sulfonated styrene / isobutylene / maleic anhydride.
  • Acid copolymers and starch / polyacrylonitrile graft copolymers can be exemplified.
  • decomposition inhibitor examples include desiccants such as zeolite, quicklime, and magnesium oxide; phenol-based, amine-based, sulfur-based, and phosphoric acid-based antioxidants; and salicylic acid-based and benzophenone-based ultraviolet absorbers. Can be mentioned.
  • the content thereof is usually 5 to 95%, preferably 20 to 90% for a carrier such as a solid carrier or a liquid carrier on a mass basis.
  • the surfactant is usually selected in the range of 0.1% to 30%, preferably 0.5 to 10%, and the other additives are 0.1 to 30%, preferably 0.5 to 30%. It is selected in the range of 1010%.
  • the pest control agent of the present invention includes powders, powders and granules, granules, wettable powders, aqueous solvents, wettable granules, tablets, jumbo, emulsions, oils, liquids, flowables, emulsions, microemulsions , Suspoemulsion, microdispersion, microcapsule, smoke agent, aerosol, bait, paste and the like.
  • these preparations When these preparations are actually used, they can be used as they are or diluted to a predetermined concentration with a diluent such as water.
  • a diluent such as water.
  • the application of various preparations containing the compound of the present invention or a dilution thereof can be carried out by a commonly used application method, that is, spraying (eg, spraying, misting, atomizing, dusting, dusting, water application, box application) Application), soil application (for example, mixing, irrigation, etc.), surface application (for example, application, dressing, coating, etc.), seed treatment (for example, smearing, dressing, etc.), immersion, poison bait, smoke application And the like. It is also possible to feed the livestock with the above-mentioned active ingredient by mixing it with the feed to control the generation and growth of harmful insects, particularly harmful insects, in their excrement.
  • the pest control method of the present invention is a method for controlling a pest according to the above-mentioned application method, wherein the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative represented by the general formula [I] of the present invention or a derivative thereof is used. It can be carried out by using an amount of an active ingredient of an agriculturally acceptable salt.
  • the mixing ratio (% by mass) of the active ingredient in the pest control agent of the present invention is appropriately selected as necessary.
  • a powder, a granule, a fine granule or the like it is appropriate to appropriately select from the range of 0.01 to 20%, preferably 0.05 to 10%. It is appropriate to appropriately select from the range of 30%, preferably from 0.5 to 20%, and in the case of a wettable powder, a wettable powder, etc., it is appropriately selected from the range of 1 to 70%, preferably 5 to 50%.
  • a water solvent or a liquid preparation it may be appropriately selected from the range of 1 to 95%, preferably 10 to 80%, and in the case of an emulsion or the like, 5 to 90%, preferably 10 to 80%. It is preferable to select an appropriate amount from the range.
  • it is appropriately selected from the range of 1 to 50%, preferably 5 to 30%. It is preferable to select an appropriate one from the range of 50%, and an emulsion, a microemulsion, In the case of a spoemulsion or the like, it is appropriate to appropriately select from the range of 5 to 70%, preferably 10 to 60%.
  • the pest control agent of the present invention When the pest control agent of the present invention is used after being diluted with a diluent, it is generally used at an active ingredient concentration of 0.1 to 5000 ppm. When the preparation is used as it is, the application rate per unit area is 0.1 to 5000 g per ha as the active ingredient compound, but is not limited thereto.
  • the pesticidal agent of the present invention is sufficiently effective even when the compound of the present invention is used alone as an active ingredient.
  • other fertilizers and pesticides for example, insecticides, pesticides, It can be mixed and used in combination with mites, nematicides, synergists, fungicides, antivirals, attractants, herbicides, plant growth regulators, etc., in which case even better effects may be exhibited. .
  • Insecticidal active ingredients Acrinathrin, azadirachtin, azamethiphos, acinonapyr, azinphos-acetyl, azinphos-acetyl, azinphos-acetyl, azinphos-acetyl, azinphos-acetate (Acetoprole), acephate, azocyclotin, abamectin, afidopyropen, afoxolaner, amideflumetrametrametrametrametamu , Alanycarb, aldicarb, aldoxycarb, allethrin [including d-cis-trans-form, d-trans-form], isazophos, isamiphos (isomidphos) Isocarbobophos, isoxathion, isocycloseram, isofenphos-methyl, isoprocarb, epsilon-methosulfon,
  • I Lumectin imiciafos, imidacloprid, imiprothrin, indoxacarb, indoxacarb, esfenvaleth, ethiophenocarb, ethiophenocarb ethifenfolate Ethylene dibromide, etoxazole, etofenprox, ethoprophos, ethofophos, etrimfos, emamectin, emamectin benzoate zoate, endosulfan, empenthrin, oxazosulfyl, oxamyl, oxamyl, oxydimetone-methyl, oxydeprotosate, oxydeprotos (fos) cadasufos, kappa-tefluthrin, kappa-bifenthrin, kappa-bifenthrin, kar
  • chlorfenapyr chlorfenvinphos, chlorfluazuron, chlormephos, chloropraresulin, sialopyrinopyrinopyrosine, sialopyrinopyrinopyrosine, and sialopyrinopyrinopyrosine, sialopyrinopyrocyranopyrinopyrosine, sialopyrinopyrinopyrophile, sialopyrinopyrinopyrinopyrinopyrinopyrinopyrinopyrinopyrinopyrinopyrnopyrophilin.
  • Liture-B aluminum phosphide (aluminium phosphide), zinc phosphide (zinc phosphide), hydrogen phosphide (phosphine), lufenuron (lufenuron), rescalure, resmethrin (resmethrin) epicinetin, rotenone, nuclear polyhedrosis virus embedding, fenbutatin oxide, calcium cyanide, organic tin compounds (organotins), nicotine sulfate (nicotine-sulphate), (nicotine-sulphate) 11-tetradecenyl acetate, (Z) -11-hexadecenal, (Z) -11-hexadecenyl acetate, (Z) -9,12-tetradecadienyl acetate, (Z) -9-tetradecen-1-ol , (Z, E) -9,11-tetradecadien
  • Fungicidal active ingredient Azaconazole, acibenzolar-S-methyl, azoxystrobin, anilazine, anisulbrom, amipyriffline, aminopyrifline, aminoprifectin aldimorph), isotianil, isopyrazam, isofetamide, isoflucipram, isoprothiolane, ipconifen, epuconazole, ipconazole, ipconazole, ipconazole, ipconazole, and ipconazole.
  • Fentriffluconazole ipfentrifluconazole
  • iprodione iprovalicarb
  • iprobenfos imazalilamine, iminotazine albecilate, iminoctazine albesilate (Imibenconazole), impirfluxam, imprimatin A, imprimatin B, edifenphos, etaconazol, ethaboxam aboxam), etirimol, ethoxyquin, ethridiazole, enestroburin, enoxastrobin, epoxiconil, oxyloxyxanol, oxyloxyl, oxyloxyl, oxyloxyl, oxyl, oxyl, oxyl, oxyl, oxyl, oxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl
  • Diflupir (benzovindiflupyr), benthiazole (benthiazole), benthiavalicarb-isopropyl, penthiopyrad, penflufen, scafylid, scafylid, scalido, scalido, scalido, scalide, boscalid, sc lcium, sodium, polyoxin, polycarbamate, bordeaux mixture, mancopper, mancozeb, mandeb, mandiopropamide Microbutanil, mineral oils, mildiomycin, methasulfocarb, metatam, metalaxyl, metalaxyl, metalaxyl, metalaxyl, metalaxyl, metalaxyl, metalaxyl Methyl tet Protol (metyltetraprole), metconazole (metconazole), methinostrobin (metaminostrobin), metrafenone (
  • Herbicidal active ingredients Ioxynil, acronifen, acrolein, azafenidin, azafenidin, acifluorfen (including salts with sodium and the like), azimsulfuron, azhamulace, ashramus (Acetochlor), atrazine (atrazine), anilofos (anilofos), amicarbazone, amidosulfuron, amitrolle, aminocyclopyrrol (amiclocyclopride), aminocyclopyracryloamidopyramylo, aminopyrrochloride, aminopyracryloamidopyramyl, aminopyrochloride, aminopyrochloride, aminopyracrylo, aminopyracrylo, aminopyracrylo, aminopyracrylamide ofos-methyl, ametrin, alachlor, alloxydim, ancymidol, isouron, isoxachlortole, isoxaflutoxol (Isoxaben), isodecyl alcohol
  • Salts such as isopropylamine No), imazametalsz (imazamethabenz-methyl), imazamox (imazamox), imazethapyr (imazethapyr), imazosulfuron (imazosulfuron), Indajifuramu (indaziflam), indanofan (indanofan), Egurinajin-ethyl (eglinazine-ethyl), esprocarb (esprocarb), Etame Tosulfuron-methyl, ethalfluralin, ethidimuron, ethoxysulfuron, ethoxyfen-ethyl, ethofumet sate), etobenzanide, endothal-disodium salt, oxadiazon, oxadiargyl, oxadiclomefone, oxazilfolon, oxasulfuron, oxasulfuron, o
  • esters such as heptanoic acid), bromophenoxime, bromobutide, florasulam, florpyrauxifen, florpyrauxifenhexyl, and florpyraxenixen-hexyl.
  • petoxamide (petoxamid), benazoline (benazolin), penoxsulam (penoxsulam), heptamaloxyloglucan (heptamaloxyloglucan), beflubutamate (beflubutamid), beflubutamate ), Bencarbazone, pendimethalin, benzfendizone, bensulide, bensulfuron-methyl, benzobicyclone, benzobicyclophenic acid Benzofenap, bentazone, pentanochlor, pentoxazone, pentoxazone, benfluralin, benfurasate, benfuresate, fosaforen, fomesafron, fomesaffen, fomesafen, formesafen Neuron (forchlorfenuron), mecoprop (including salts such as sodium, potassium, isopropylamine, triethanolamine, dimethylamine), mecoprop-P-potassium salt, mecosulfuron (mesosulf
  • Plant growth regulator 1-naphthylacetamide, 1-methylcyclopropene, 2,6-diisopropylnaphthalene, 2, oxo-4- (2-phenylethyl) aminobutyric acid, Chemical name, CAS registry number: 1083-55-2), 4-chlorophenoxyacetic acid (4-CPA), n-decyl alcohol (n-decanol), aviglycine, ancymidol, abscisic acid ( abscisic acid, inabenfide, indole acetic acid, indole butyric acid (indole butyric acid) id), uniconazole, uniconazole-P, unicozole-P, ecolist, ethiclozate, ethephon, ethephon, epocholeone, oxine sulfate, oxine sulfate ), Calcium formate (calcium formate), cloxyfonac (cloxyfonac
  • Isoxadifen isoxadifen-ethyl, oxabetrinil, cloquintcet-mexyl, dietholate, dimethoate, dimethoate Cyprosulfamide, naphthalic anhydride (1,8-Naphthalic @ Anhydride), fenchlorazole-O-ethyl, fenchlorim, furilazole, furixazole uxofenim), flurazole, benoxacor, mephenate, mefenpyr, mefenpyr-ethyl, mefenpyr-diethyl, mefenpyr-diethyl, lower alkyl, substituted lower alkyl, mefenpyr-diethyl 2-dichloro-N- (1,3-dioxan-2-ylmethyl) -N- (2-propenyl) acetamide (PPG-1292), 2-dichloromethyl-2-methyl-1,3-dioxan
  • the pest control agent of the present invention configured as described above includes grasshopper pests, thrips pests, stinkbug pests, crustacean pests, fly eye pests, lepidopteran pests, wasp order pests, coleoptera, pests Pests, cockroach pests, chapterae pests, whiteflies pests, lice pests, plant parasitic mites, plant parasitic nematodes, plant parasitic molluscs, other pests, unpleasant animals, sanitary pests, parasites It has an excellent control effect against pests such as Examples of such pests include the following species.
  • grasshopper pests include, for example, Ruspolia lineeosa of the family Grassicaceae, emerma crickets of the cricket family (Teleogrylus emma), and green worms (Truljalia hibinoni of the family Keragina (Galina), such as Kera (Galenta pallidae).
  • the Thysanoptera for example, of the thrips family Hirazuhanaazamiuma (Frankliniella intonsa), western flower thrips (Frankliniella occidentalis), yellow tea thrips (Scirtothrips dorsalis), southern thrips (Thrips palmi), green onion thrips (Thrips tabaci), Daizuusu Thrips thrips (Thrips @ setosus), Croton thrips (Heliothrips @ haemorrhoidalis), Rice thrips (Stenchaethotrips @ biformis), etc., of the family Thrips thrips (Thrips thrips).
  • Wasabi Kuda thrips Liothrips wasabiae
  • rice Kedah thrips Haplothrips aculeatus
  • stink bug pests include, for example, the cicada family, Iwaki-kami-semi (Mogannia @ minuta), the Aphid beetle family (Aphrophora @ intermedia), the sugarcane spitbug (Mahanarva @ fimbriata, and the like), and the like.
  • Leafhoppers of the leafhopper family (Arbordia @ apicalis), Leafhoppers (Empoasca @ onukii), Leafhoppers (Nephotettix @ cincticeps), and Leafhopper Leafhoppers (Nephotettix) ens), cross di leafhopper (Nephotettix nigropictus), Inazuma leafhopper (Recilia dorsalis), okra leaf hopper (Amrasca biguttula), mango leaf hopper (Idioscopus nitidulus, Idioscopus clypealis, Amritodus atkinsoni), Inazuma leafhopper (Recilia dorsalis), potato leaf hopper (Empoasca @ fabae), corn leaf hoppers (Dalbulus @ maidis), etc., and the brown planthopper (Pentastiridius @ apicalis), etc.
  • the family of the family Carnidae (Nissia acer), such as the family of the family Siracusa (Nissia), and the family of the family of the family Siracusa (Ricaceae), Bacillus serrata (Achirus @ flammeus), etc., Orosanga @ japonicus, etc., Aobahagoromo family, etc., Mimophantia @ maritima, etc .; ri) and others; Calophya mangiferae of the family Lamiaceae; Daktulosphaira vitifoliae of the family Philoxera; In the families, Aphirosiphon apisum, Aphis gossypii, Aphis gossypii, Aphispiraecola, Aphid aphisii, Aphis mosaic blossoms ersicae), wheat midge aphid (Schizzaphis @ graminum), wheat aphid (Rhopa
  • Leptocorisa chinensis Examples include the stink bug (Rhopalus maculatus), the lower bug stink bug (Scaptocoris @ castanea), the bed bug (Cimex @ lectularis), and the like.
  • the Coleoptera for example, cupreous chafer of Scarabaeidae (Anomara cuprea), rufocuprea (Anomara rufocuprea), Japanese beetle (Popillia japonica), core Oh flower chafer (Oxycetonia jucunda), Sakura Tsurukogane (Anomala geniculata), rhinoceros beetle (Oryctes rhinoceros) , (Heptophylla @ picea), Phyllophaga @ cuyabana, etc., of the family Beetle Beetle (Agriotes ogreas Aegeos ogreus).
  • Cryptocarpium scrophleus in the family Cuboptera scents such as Carpophilus hemipterus and Pollen beetle (Meligethes aeneus); Tentami (Epilachna @ varirivestis), T. japonica (Henosepilachna @ vigintioctopunctata), etc. of the Tenebrionidae family (Tenebrio molitor, etc.), etc.
  • Leaf beetles Colorado potato beetle Leaf beetle (Leptinotarsa decemlineata), Western corn root worm (Diabrotica virgifera virgifera), Northern corn root worm (Diabrotica barberi), Southern koa Rootworm (Diabrotica undecimpunctata howardi), cucurbit leaf beetle (Aulacophora femoralis), radish leaf beetle (Phaedon brassicae), Kamenokohamushi (Cassida nebulosa), Inedorooimushi (Oulema oryzae), Mexican beetle (Epilachna varivestis), Kisujinomihamushi (Phyllotreta striolata), Madara Kasahara beetle ( Demotina @ fasciculata, cabage stem flare beetle (Psyliodes @ chrysocephala), bean leaf beetle (Cer
  • Examples of pests of the order Fly flies include, for example, the swordfish (Tipula aino) and the fly fly bag (Plecia nearctica) and the mushroom fly larva (Execia shiitakevora) and the mosquito scallop and the like.
  • Bivalve mushrooms Pnyxia scabiei
  • Blysia mushrooms Blysia mushrooms (Bradysia agrestis), etc.
  • soybean flies Asphonylia yusimai
  • Hesian flies Mayetiola ⁇ st ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ Culex pipiens (Culex @ pip ens @ pallens, etc .; Simulium @ takahashii, etc .; Chironomus @ oryzae, etc .; Afidae, Chrynobus @ suavis; ); Fly (Agromyza oryzae), eggplant leafminer (Liriomyza bryoniae), the pea (Chromatomyia horticola), green onion leafminer (Liriomyza chinensis), such as American cell pen Tin leaf minor
  • Lepidoptera pests include, but are not limited to, Endoclita excrescens, bats of the family bat, Endospila ⁇ ampelopsia of the family of the family bats, etc .; Sea oysters (Archips @ fuscocupreanus), apple lizards (Adoxophys ⁇ orana ⁇ fasciata), Nashihimesingui (Grapholita @ molesta), chahamaki (Homona @ magnaigina, L. monella), European grape vine moss (Lobesia botrana), etc., Grape Hosohamaki (Eupoecilia ambiguella), etc.
  • Geometridae family of Artemisia Eda Shakti (Ascotis selenaria), pine moth (Dendrolimus spectabilis of lasiocampidae), lackey moth (Malacosoma neustrium testaceum), etc., AGRIUS CONVOLVULI of sphingidae (Agrius convolvuli), etc., of Lymantriidae Arna Pseudoconspersa (Arna pseudoconspersa ), Orygiafur approximans, Lymantria dispar, and others, such as Hyphantria cunea, belonging to the family Noctuidae, and Agrotis ggigas, Agrotis gigas, from the family Noctuidae.
  • honey bee pests examples include, for example, the wasp-family spp. (Agephygana), the wasp-family chestnut wasp (Apethymus kuri), the squamf wasp (Athalia rosae ruficornis), and the bee-family Drikyuurusi (C.) Ants (Solenopsis @ invicta), such as the Japanese hornet (Vespa @ simillima @ xanthoptera), and the ant family (Solenopsis @ invicta), and the Argentine ant (Lineipithema @ humile), etc., can be mentioned.
  • Examples of the order Pests from the order of the order Tabanida include, for example, Bourletiella Hortensis of the family Martaviridae.
  • Lepidoptera As examples of the pests of Lepidoptera, there may be mentioned, for example, Lepidoptera saccharina (Lepidoptera) and Ctenolepisma (Vilosa).
  • cockroach pests for example, cockroaches (Periplaneta @americana), German cockroaches (Blattella @germanica), termites of the termite family (Odontotermes @ Formicidae), and termites of the termites of the genus Asterica sect. (Cryptotermes @ domesticus), termites of the family Termite (Copterotermes @ formosanus), and termites (Reticulitermes @ speratus).
  • insect pests of the order Psocoptera include, for example, Trochomium (Pulsatorium) of the family Papilionidae, and Usgrochatate (Liposcelis @ corrodens) of the family Papilionidae.
  • earwig pests include, for example, Laberadidae (Labobodura riparia) belonging to the family Parasitidae.
  • insects of the order Lepidoptera include, for example, chicks of the family Apocynidae, such as the chicks of the family Apocynidae, and the lice of the family Psyllidae, Damalinia bovis.
  • Examples of the lice pests include, for example, Haematopinus suis of the family Lamiidae, Pediculus humanus of the Laceae family, and the like and the genus Pis of the genus Pseudocephalus (Lingnathus tosetosus), such as the louse lice of the genus Lepidoptera, Licegrass. Can be.
  • acarid pests include, for example, the house dust mite (Penthaleus major), the dust mite Cyclamen mite (Phytonemus pallidus), the typhoid mite (Polyphagotarsononemus latus), and the species of the family Dermatophagidae: And other spider mites (Eotetranychus mite) (Panionychus mite), such as the red mite (Brevipalpus lewisi), the spider mite (Tuckerella pavoniformis), and the spider mite (Eotetranychus mite).
  • the plant parasitic nematodes include, for example, a grape nematode (Xipinema index) of the family Longidols, a paratrichodor nematode (Paratrichodorus minor) of the family Trichodulaceae, a species of the family Rhabditela sp.
  • tea pin nematodes of Paratirenkusu Department (Paratylenchus curvitatus), of Meroidogine Department of sweet potato root-knot nematode (Meloidogyne incognita), northern root-knot nematode (Meloidogyne hapla), Javanese root-knot nematode (Meloidogyne javanica), Columbia root-knot nematode (Meloidogyne chitwoodi), false Potato cyst nematodes (Globodera rostochiensis) of the family Heterodela, such as Colombian root knot nematodes (Meloidogyne fallax), potato cyst nematodes (Globodera pallida), soybean cysts Species of the family Psyllenchus (Psilenidae), such as the genus Psinus, Psylenchus (Hymenoptera), such as He
  • plant-parasitic molluscs examples include, for example, Pomicea canaliculata and the like of the family Papilionidae, Levicaulis @alte of the family Aphididae, and Achatina @flicica of the family Achamidae and the like.
  • Species of the family Agonaceae such as Schimuxia sect.
  • pests such as pests, unpleasant animals, sanitary pests, livestock pests, and parasites
  • examples of other pests include, for example, a crayfish of the order Crayfish (Procambarus @ clarkii), a porphyria of the order Coleoptera, Porcellio @ scaber, and the like.
  • Etc . Armadillidium vulgare
  • Chiracan spiders of the order Araneidae such as the redback spider (Therididae @ hasseltii) of the order Spiderae worms (Ascaris @ lumbricoides), etc.
  • the pest control agent of the present invention has a control effect on the pests and the like exemplified above, which have acquired resistance to the existing pest control agent.
  • the pesticidal composition of the present invention can also be used for plants that have acquired characteristics such as insect resistance, disease resistance, and herbicide resistance by genetic recombination, artificial crossing, and the like.
  • plant to which resistance has been imparted by a breeding method or a genetic recombination technique means not only resistance imparting by classical breeding and genetic conferring techniques, but also molecular biology Also include plants to which resistance has been imparted by a new breeding technique (New Plant Breeding Technologies, NBTs) that combines conventional techniques.
  • New breeding techniques are described in the book “Let's Understand New Plant Breeding Techniques” (International Literature Company, Ryo Osawa, Hiroshi Emen), review article “Genome Editing Tools” in Plants (Genes 2017, 8, 399, Tapan Kumar Moanta). Tufail, Bashir, Abeer, Hashem, Elsayed, Fathi, Abd_Allah, and Hanghong, Bae).
  • the melting point which is the physical property value of the compound of the present invention
  • the refractive index was measured using an Atago Abbe refractometer.
  • the 1 H NMR spectrum was measured using JNM-LA400 (400 MHz), JNM-LA300 (300 MHz) or JNM-ECS300 (300 MHz) manufactured by JEOL with tetramethylsilane (TMS) as an internal standard.
  • reaction mixture was concentrated under reduced pressure, and a 10% aqueous citric acid solution was added to the residue to acidify the reaction mixture, thereby depositing a solid.
  • the solid was filtered, washed with water, and dried to obtain 6.09 g of a crude target product (yield: 93%).
  • reaction mixture was concentrated under reduced pressure, and a 10% aqueous citric acid solution was added to the residue to acidify the reaction mixture, thereby depositing a solid.
  • the solid was filtered, washed with water, and dried to obtain 0.63 g (yield 91%) of a crude target product.
  • Ethyl 4-fluoro-2-methyl-5- [5-methyl-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] benzoate (Compound No. of the present invention: Preparation of C-0109) Ethyl 5- [2- (1-amino-2,2,2-trifluoroethylidene) hydrazinyl] -4-fluoro-2-methylbenzoate 1.27 g (4.13 mmol) of N, To 10 mL of the N-dimethylacetamide solution was added 0.49 g (6.2 mmol) of acetyl chloride under ice-cooling, followed by stirring at 140 ° C. for 1 hour.
  • A-0212 of the present invention 5- [5-chloro-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro 0.23 g (1.7 mmol) of potassium carbonate was added to 20 mL of a methanol solution of 0.55 g (1.4 mmol) of -2-methyl-N- (2,2,2-trifluoroethyl) benzoic acid amide, and the mixture was added at room temperature. Stir for 4 hours.
  • A-2170 of the present invention (1) Production of di (2,2,2-trifluoroethyl) N-cyanodithiocarboxyimino acid
  • Trifluoromethanesulfonic acid 2,2,2 was added to 50 mL of a dimethyl sulfoxide solution of 7.00 g (36.0 mmol) of dipotassium N-cyanodithiocarboxyiminoate prepared according to the method described in Patent Publication WO 1994/026706 under ice-cooling. 20.06 g (86.43 mmol) of 2-trifluoroethyl was added, and the mixture was stirred at room temperature for 67 hours.
  • the solvent was distilled off under reduced pressure, and the residue was dissolved in 100 mL of methanol. Under ice-cooling, 17.12 g (123.9 mmol) of potassium carbonate was added, and the mixture was stirred at room temperature for 5.5 hours. After adjusting the pH to 5 by adding hydrochloric acid, saturated saline was added, and the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude target product. This was used for the next step without purification.
  • reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and brine, and dried over anhydrous magnesium sulfate.
  • Example 13 5- [3-chloro-5-methyl-1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl-N- (2,2,2-trifluoroethyl) benzoic acid amide Preparation of (Compound No. A-2453 of the present invention) (1) 5- (3-chloro-5-methyl-1H-1,2,4-triazol-1-yl) -4-fluoro-2-methylbenzoic acid Of ethyl acetate (Compound No.
  • Formulation Example 4 Granules Compounds listed in Tables 1 to 25 and 59 to 70 5 parts Sodium salt of lauryl alcohol sulfate 2 parts Sodium lignin sulfonate 5 parts Carboxymethyl cellulose 2 parts Clay 86 parts It was mixed and ground. 20 parts of water was added to the mixture, and the mixture was kneaded, processed into granules of 14 to 32 mesh using an extrusion granulator, and dried to obtain granules.
  • Insecticidal insecticidal activity test A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm as an active ingredient. Cabbage leaves were immersed in the chemical solution, air-dried, and then placed in a plastic cup. 10 second instar larvae of the Japanese moth were released into it and covered. After that, it was placed in a constant temperature room at 25 ° C., and after 6 days, the number of dead insects was examined, and the mortality was calculated by the formula (1). The test was performed in a single system.
  • Test for insecticidal activity of brown planthoppers The wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm as an active ingredient. Rice sprouting paddy was immersed in the chemical solution and placed in a plastic cup. Ten plastic brown planthopper second-instar larvae were released into the plastic cup, and the lid was closed. After that, it was placed in a constant temperature room at 25 ° C., and after 6 days, the number of dead insects was examined, and the mortality was calculated by the formula (1). The test was performed in a single system.
  • 35 of the comparative compound (described in WO 2017/012970) showed no activity at a concentration of 500 ppm.
  • Test for controlling effects of spider mites A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm as an active ingredient. Soybean seedlings inoculated with 35 adult female spider mites were soaked in the chemical solution and air-dried. The soybean seedlings after the treatment were placed in a constant temperature room at 25 ° C., and after 13 days, the number of surviving female adult insects was examined, and the control value was calculated according to the equation (2). The test was performed in a single system.
  • 35 of the comparative compound (described in WO 2017/012970) showed no activity at a concentration of 500 ppm.
  • Test for controlling nematode activity of root-knot nematode of sweet potato The test compound was dissolved in N, N-dimethylformamide containing 1% of tween 20, and this solution was diluted with water to a concentration of 20 ppm as an active ingredient. 0.5 ml of the drug solution and 0.5 ml of a suspension containing about 30 second stage larvae of the root-knot nematode were mixed to give a concentration of 10 ppm as an active ingredient, and placed in a thermostatic chamber at 25 ° C. Five days later, the number of surviving nematodes was counted under a microscope, and the control activity of the nematodes was calculated by the formula of Equation 3. The test was performed in a two-part system.
  • 35 of the comparative compound (described in WO2017 / 012970) showed no activity at a concentration of 10 ppm.
  • the compound of the present invention represented by the general formula [I] or a salt thereof has an excellent pest control effect and is useful as an active ingredient such as an agricultural chemical or an insecticide. Further, the compound represented by the general formula [II] of the present invention and the compound represented by the general formula [III] of the present invention are useful as intermediates for producing the compound represented by the general formula [I].
  • the present invention has industrial applicability in these fields and the like.

Abstract

The present invention addresses the problem of providing a superior harmful organism control agent. Provided are the 3-(1H-1,2,4-triazole-1-yl) benzoic acid amide derivative shown in general formula [I] or an agrochemically permissible salt thereof, and a harmful organism control agent that is characterized by including the same as an active component (in the formula, R1 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group, or similar, R2 represents a hydrogen atom or similar, A represents an oxygen atom or a sulfur atom, R3 represents a halogen atom, a C1-C6 alkyl group, or similar, n represents an integer from 0 to 3, R4 represents a halogen atom, a C1-C6 alkyl group, or similar, R5 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, -NH2, -N(R12)R14, or similar, and R6 represents a hydrogen atom, a C1-C6 alkyl group, -NH2, -N(R12)R14, -N(R10)C(=O)R14, or similar).

Description

３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体及び有害生物防除剤3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivatives and pesticides
　本発明は、新規な３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩、該誘導体又はその塩を有効成分として含有する有害生物防除剤及び製造中間体に関するものである。 The present invention relates to a novel 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or an agriculturally acceptable salt thereof, and a pest control containing the derivative or its salt as an active ingredient. It relates to an agent and a production intermediate.
　特許文献１と２には、有害生物防除効果を有する３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体が記載されている。特許文献１と２に記載の化合物は、安息香酸アミドの３位に結合したトリアゾール環の３位に１Ｈ－ピラゾール－５－イル基が結合した化合物に限定されている。 Patent Documents 1 and 2 describe 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivatives having a pest control effect. The compounds described in Patent Documents 1 and 2 are limited to compounds in which a 1H-pyrazol-5-yl group is bonded to the 3-position of a triazole ring bonded to the 3-position of benzoic acid amide.
　特許文献３には、Ｐ２Ｘ３またはＰ２Ｘ２／３受容体アンタゴニスト活性を有する３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体が記載されている。特許文献３に記載の化合物は、安息香酸アミドの５位に、５－メチルピリジン－２－イル基が結合した化合物に限定されている。さらに、特許文献３には、殺虫活性に関する記載もない。 Patent Document 3 describes a 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative having P2X3 or P2X2 / 3 receptor antagonist activity. The compounds described in Patent Document 3 are limited to compounds in which a 5-methylpyridin-2-yl group is bonded to the 5-position of benzoic acid amide. Furthermore, Patent Document 3 has no description on insecticidal activity.
　特許文献４には、Ｐ２Ｘ７受容体阻害活性を有する安息香酸アミド誘導体が記載されている。特許文献４に記載の化合物は、安息香酸アミドの３位に、４，５－ジヒドロ－５－オキソ－１Ｈ－１，２，４－トリアゾール－１－イル基が結合した化合物であるが、Ｎ－（ヒドロキシ置換シクロアルキルアルキル）安息香酸アミドに限定されている。さらに、特許文献４には、殺虫活性に関する記載もない。 Patent Document 4 describes a benzoic acid amide derivative having P2X7 receptor inhibitory activity. The compound described in Patent Document 4 is a compound in which a 4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl group is bonded to the 3-position of benzoic acid amide, Limited to-(hydroxy-substituted cycloalkylalkyl) benzoic acid amides. Further, Patent Document 4 has no description on insecticidal activity.
　特許文献５には、除草活性を有するフェニルスルファモイルカルボキサミド誘導体が記載されている。特許文献５に記載の化合物は、フェニルスルファモイルカルボキサミドの３位に、４，５－ジヒドロ－５－オキソ－１Ｈ－１，２，４－トリアゾール－１－イル基が結合した化合物に限定されている。さらに、特許文献５には、殺虫活性に関する記載もない。 Patent Document 5 describes a phenylsulfamoylcarboxamide derivative having herbicidal activity. The compound described in Patent Document 5 is limited to a compound in which a 4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl group is bonded to the 3-position of phenylsulfamoylcarboxamide. ing. Furthermore, Patent Document 5 has no description on insecticidal activity.
　特許文献６には、Ｘａ因子阻害活性を有する３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体が記載されている。特許文献６に記載の化合物は、トリアゾール環の５位に、フェニルアミノカルボニル基、ピリジルアミノカルボニル基、ピリミジニルアミノカルボニル基が結合した化合物に限定されている。さらに、特許文献６には、殺虫活性に関する記載もない。 Patent Document 6 describes a 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative having factor Xa inhibitory activity. The compounds described in Patent Document 6 are limited to compounds in which a phenylaminocarbonyl group, a pyridylaminocarbonyl group, and a pyrimidinylaminocarbonyl group are bonded to the 5-position of a triazole ring. Furthermore, Patent Document 6 has no description on insecticidal activity.
国際公開第２０１７／１０８５６９号International Publication No. WO 2017/108569 国際公開第２０１７／０１２９７０号International Publication No. WO 2017/012970 国際公開第２００９／０７７３６６号International Publication No. 2009/077366 国際公開第２００４／０５８７３１号International Publication No. 2004/058731 国際公開第２００１／０８３４５９号WO 2001/083459 国際公開第１９９８／０２８２６９号International Publication No. 1998/028269
　有用作物に対して使用される有害生物防除剤は、土壌又は茎葉に施用し、低薬量で十分な有害生物防除効果を示す薬剤であることが望まれている。また、化学物質の安全性、環境に対する影響への要求が高まってきており、より安全な有害生物防除剤の開発が望まれている。更に、近年、殺虫剤、殺ダニ剤、殺センチュウ剤等の有害生物防除剤を長年にわたって使用する事により、その有害生物防除剤に対して抵抗性を獲得した有害生物が出現してきており、そのため、有害生物を完全に防除することが困難になっている。また、人畜毒性の高い有害生物妨除剤の使用についても、作業者に対する安全性等の面で問題となっている。 (4) Pest control agents used for useful crops are desired to be applied to soil or foliage and show sufficient pest control effects at a low dose. In addition, the demand for the safety of chemical substances and the effect on the environment has been increasing, and the development of safer pest control agents has been desired. Furthermore, in recent years, by using pesticides such as insecticides, acaricides, nematodes, etc. for many years, pests that have acquired resistance to the pesticides have emerged. It has become difficult to completely control pests. Also, the use of pesticides with high human toxicity is a problem in terms of safety for workers.
　本発明の課題は、このような事情の中、従来の有害生物防除剤が有していた前記の如き問題点を解決し、更に、安全性、防除効果、残効性等に優れた有害生物防除剤、及びそのための新規な化合物を提供することにある。 Under such circumstances, an object of the present invention is to solve the above-mentioned problems of a conventional pest control agent, and furthermore, to provide a pest excellent in safety, control effect, residual effect and the like. An object of the present invention is to provide a controlling agent and a novel compound therefor.
　本発明者らは、前記した好ましい特性を有する有害生物防除剤を開発するために、種々の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体を合成し、その生理活性について鋭意検討を行った。その結果、下記の一般式［Ｉ］で示される３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体（以下、本発明の化合物ともいう。）が種々の有害生物に対して優れた防除効果を有することを見い出し、更に研究を続けて本発明を完成したものである。 The present inventors have synthesized various 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivatives and developed their pest control agents having the above-mentioned preferable properties. We studied diligently about physiological activity. As a result, 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivatives (hereinafter, also referred to as compounds of the present invention) represented by the following general formula [I] can be used for various pests. The present invention has been found to have an excellent control effect on, and the present invention has been completed by further study.
　即ち、本発明は、下記の事項に関するものである。
（１）一般式［Ｉ］ That is, the present invention relates to the following matters.
(1) General formula [I]
Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000010
　[式中、
　Ｒ１は、水素原子、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｒ８によって任意に置換されたＣ３～Ｃ６シクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、－ＮＨ２、－Ｎ（Ｒ９）Ｒ１０、－ＯＨ、－ＯＲ１１、－Ｓ（＝Ｏ）２Ｒ１１、－ＣＨ＝ＮＯＲ１１又は飽和複素環を示し、
　Ｒ２は、水素原子、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、－Ｓ（＝Ｏ）２Ｒ１１、－Ｃ（＝Ｏ）Ｒ１１、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１１を示すか、或いは、Ｒ１及びＲ２は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく
　Ａは、酸素原子又は硫黄原子を示し、
　Ｒ３は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、－ＮＨ２、－Ｎ（Ｒ９）Ｒ１０、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｓ）ＮＨ２を示し、
　ｎは、０～３の整数を示し、
　Ｒ４は、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、－ＮＨ２又は－Ｎ（Ｒ９）Ｒ１０を示し、
　Ｒ５は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｒ８によって任意に置換されたＣ３～Ｃ６シクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｒ１３によって任意に置換されたＣ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｒ１３によって任意に置換されたＣ２～Ｃ６アルキニル基、－ＯＨ、－ＯＣ（＝Ｏ）Ｒ１４、－ＯＳ（＝Ｏ）２Ｒ１４、－ＯＳｉ（Ｒ１４）２Ｒ１２、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルコキシ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルコキシ基、Ｃ２～Ｃ６アルケニルオキシ基、Ｃ２～Ｃ６ハロアルケニルオキシ基、Ｃ２～Ｃ６アルキニルオキシ基、Ｃ２～Ｃ６ハロアルキニルオキシ基、Ｃ３～Ｃ６シクロアルキルオキシ基、Ｃ３～Ｃ６ハロシクロアルキルオキシ基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルオキシ基、芳香族複素環オキシ基、飽和複素環オキシ基、－ＳＨ、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルチオ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルスルフィニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルスルホニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルチオ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルスルフィニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルスルホニル基、Ｃ２～Ｃ６アルケニルチオ基、Ｃ２～Ｃ６アルケニルスルフィニル基、Ｃ２～Ｃ６アルケニルスルホニル基、Ｃ２～Ｃ６ハロアルケニルチオ基、Ｃ２～Ｃ６ハロアルケニルスルフィニル基、Ｃ２～Ｃ６ハロアルケニルスルホニル基、Ｃ２～Ｃ６アルキニルチオ基、Ｃ２～Ｃ６アルキニルスルフィニル基、Ｃ２～Ｃ６アルキニルスルホニル基、Ｃ３～Ｃ６シクロアルキルチオ基、Ｃ３～Ｃ６シクロアルキルスルフィニル基、Ｃ３～Ｃ６シクロアルキルスルホニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルチオ基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルスルフィニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルスルホニル基、芳香族複素環チオ基、芳香族複素環スルフィニル基、芳香族複素環スルホニル基、飽和複素環チオ基、飽和複素環スルフィニル基、飽和複素環スルホニル基、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１４、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｃ（Ｒ１５）＝ＮＯＨ又は－Ｃ（Ｒ１５）＝ＮＯＲ１４を示し、
　Ｒ６は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルコキシ基、Ｃ２～Ｃ６アルケニルオキシ基、Ｃ２～Ｃ６ハロアルケニルオキシ基、Ｃ２～Ｃ６アルキニルオキシ基、Ｃ２～Ｃ６ハロアルキニルオキシ基、Ｃ３～Ｃ６シクロアルキルオキシ基、Ｃ３～Ｃ６ハロシクロアルキルオキシ基、－ＳＨ、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、Ｃ２～Ｃ６アルケニルチオ基、Ｃ２～Ｃ６アルケニルスルフィニル基、Ｃ２～Ｃ６アルケニルスルホニル基、Ｃ２～Ｃ６アルキニルチオ基、Ｃ２～Ｃ６アルキニルスルフィニル基、Ｃ２～Ｃ６アルキニルスルホニル基、Ｃ３～Ｃ６シクロアルキルチオ基、Ｃ３～Ｃ６シクロアルキルスルフィニル基、Ｃ３～Ｃ６シクロアルキルスルホニル基、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｎ＝Ｃ（Ｒ１２）Ｒ１４、－Ｎ＝Ｃ（Ｒ１５）Ｎ（Ｒ１２）Ｒ１４、－ＮＨＣ（Ｒ１５）＝ＮＯＲ１４、－Ｎ＝Ｓ（Ｒ１４）Ｒ１２、－Ｎ＝Ｓ（＝Ｏ）（Ｒ１４）Ｒ１２、－Ｎ（Ｒ１０）ＮＨ２、－Ｎ（Ｒ１０）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（Ｒ１５）＝ＮＯＨ、－Ｃ（Ｒ１５）＝ＮＯＲ１４、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１４、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
　Ｒ７は、シアノ基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
　Ｒ８は、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
　Ｒ９は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ３～Ｃ６シクロアルキル基、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１１、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１又は－Ｓ（＝Ｏ）２Ｒ１１を示し、
　Ｒ１０は、水素原子、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ３～Ｃ６シクロアルキル基、－Ｃ（＝Ｏ）Ｒ１１、－Ｃ（＝Ｏ）ＯＲ１１又は－Ｓ（＝Ｏ）２Ｒ１１を示すか、或いは、Ｒ９及びＲ１０は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
　Ｒ１１は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示し、
　Ｒ１２は、水素原子、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示すか、或いは、Ｒ１１及びＲ１２は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
　Ｒ１３は、シアノ基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－ＯＨ、－ＯＲ１４、－ＯＣ（＝Ｏ）Ｒ１４、－ＯＳ（＝Ｏ）２Ｒ１４、－ＯＳｉ（Ｒ１４）２Ｒ１２、－ＳＨ、－ＳＲ１４、－Ｓ（＝Ｏ）Ｒ１４、－Ｓ（＝Ｏ）２Ｒ１４、－Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１４、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｓ）ＮＨ２、－Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（Ｒ１５）＝ＮＯＨ、－Ｃ（Ｒ１５）＝ＮＯＲ１４、－Ｓｉ（Ｒ１４）２Ｒ１２、無置換若しくは（Ｚ）ｐ１により置換されたフェニル基、芳香族複素環又は飽和複素環を示し、
　Ｒ１４は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルＣ１～Ｃ６アルキル基、芳香族複素環、芳香族複素環Ｃ１～Ｃ６アルキル基、飽和複素環又は飽和複素環Ｃ１～Ｃ６アルキル基を示すか、或いは、Ｒ１２及びＲ１４は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
　Ｒ１５は、水素原子、ハロゲン原子、－ＮＨ２、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示すか、或いは、Ｒ１４及びＲ１５は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
　Ｚは、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、－ＮＨ２、モノ（Ｃ１～Ｃ６アルキル）アミノ基、ジ（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルキルカルボニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルキルカルボニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルコキシカルボニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルコキシカルボニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルキルスルホニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルキルスルホニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６ハロアルキルスルホニルアミノ基、Ｎ－（Ｃ１～Ｃ６ハロアルキルスルホニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、－Ｃ（＝Ｏ）ＮＨ２、モノ（Ｃ１～Ｃ６アルキル）アミノカルボニル基、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル基、モノ（Ｃ１～Ｃ６ハロアルキル）アミノカルボニル基又はフェニル基を示し、
　芳香族複素環は、 [Where,
R 1 is a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkyl group optionally substituted by R 7 , a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, C 3 -C 6 cycloalkyl group optionally substituted by R 8 , C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl group, C 2 -C 6 alkynyl group, A C 2 -C 6 haloalkynyl group, —NH 2 , —N (R 9 ) R 10 , —OH, —OR 11 , —S (＝ O) 2 R 11 , —CH ＝ NOR 11 or a saturated heterocyclic ring ,
R 2 is a hydrogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkyl group optionally substituted by R 7 , a C 3 -C 6 cycloalkyl group , A C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, —S (＝ O) 2 R 11 , —C (＝ O) R 11 , —C (＝ O) OR 11 , —C (＝ O ) NH 2 , —C (＝ O) N (R 12 ) R 11 or —C (＝ O) N (R 12 ) OR 11 , or R 1 and R 2 are bonded to each other to form C A 2 to C 6 alkylene bond may be formed, wherein the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom, and the C 2 -C 6 alkylene bond may be a halogen atom or C 1 -C 6 may be mono- or poly-substituted by an alkyl group. A child or a sulfur atom;
R 3 is a halogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylthio group, a C 1 -C 6 alkylsulfinyl group , C 1 -C 6 alkylsulfonyl group, —NH 2 , —N (R 9 ) R 10 , —C (＝ O) NH 2 or —C (＝ S) NH 2 ,
n represents an integer of 0 to 3,
R 4 is a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano group, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl Groups, C 2 -C 6 alkynyl groups, C 2 -C 6 haloalkynyl groups, —OH, C 1 -C 6 alkoxy groups, C 1 -C 6 haloalkoxy groups, C 1 -C 6 alkylthio groups, C 1- C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group, —NH 2 or —N (R 9 ) R 10 ,
R 5 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, C 1 ~ C 6 alkyl group, C 1 ~ C 6 haloalkyl group, C 1 ~ C 6 alkyl group optionally substituted by R 13, R 13 C 1 ~ C 6 haloalkyl group optionally substituted by, C 3 ~ C 6 cycloalkyl group, C 3 ~ C 6 halocycloalkyl group, C 3 ~ C 6 cycloalkyl group optionally substituted by R 8, C 2 ~ C 6 alkenyl group, C 2 ~ C 6 haloalkenyl group, C 2 ~ C 6 alkenyl group optionally substituted by R 13, C 2 ~ C 6 alkynyl group, C 2 ~ C 6 haloalkynyl group, A C 2 -C 6 alkynyl group optionally substituted with R 13 , —OH, —OC (＝ O) R 14 , —OS (＝ O) 2 R 14 , —OSi (R 14 ) 2 R 12 , C 1 ~ C Alkoxy group, C 1 ~ C 6 haloalkoxy group, C 1 ~ C 6 alkoxy group optionally substituted by R 13, C 1 ~ C 6 haloalkoxy group optionally substituted by R 13, C 2 ~ C 6 Alkenyloxy group, C 2 -C 6 haloalkenyloxy group, C 2 -C 6 alkynyloxy group, C 2 -C 6 haloalkynyloxy group, C 3 -C 6 cycloalkyloxy group, C 3 -C 6 halocyclo Alkyloxy group, unsubstituted or substituted by (Z) p 1 phenyloxy group, aromatic heterocyclic oxy group, saturated heterocyclic oxy group, —SH, C 1 -C 6 alkylthio group, C 1 -C 6 alkyl sulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 B alkylsulfonyl group, C 1 ~ C 6 alkylthio group optionally substituted by R 13, C which is optionally substituted by R 13 1 ~ C 6 alkylsulfinyl group, C 1 ~ C which is optionally substituted by R 13 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group optionally substituted by R 13, C 1 ~ C 6 haloalkylsulfenyl optionally substituted by R 13 sulfinyl group, C 1 ~ optionally substituted by R 13 C 6 haloalkylsulfonyl group, C 2 ~ C 6 alkenylthio group, C 2 ~ C 6 alkenylsulfinyl group, C 2 ~ C 6 alkenyl sulfonyl group, C 2 ~ C 6 haloalkenyl two thio group, C 2 ~ C 6 haloalkenyl A sulfinyl group, a C 2 -C 6 haloalkenylsulfonyl group, a C 2 -C 6 alkynylthio group, C 2 ~ C 6 alkynylsulfinyl group, C 2 ~ C 6 alkynyl-sulfonyl group, C 3 ~ C 6 cycloalkylthio group, C 3 ~ C 6 cycloalkyl alkylsulfinyl group, C 3 ~ C 6 cycloalkyl alkylsulfonyl group, an unsubstituted or (Z) phenylthio group substituted by p 1, an unsubstituted or (Z) phenyl sulfinyl group substituted by p 1, an unsubstituted or (Z) phenylsulfonyl group substituted by p 1, an aromatic heterocyclic thio group An aromatic heterocyclic sulfinyl group, an aromatic heterocyclic sulfonyl group, a saturated heterocyclic thio group, a saturated heterocyclic sulfinyl group, a saturated heterocyclic sulfonyl group, -NH 2 , -N (R 12 ) R 14 , -N (R 10) C (= O) H , -N (R 10) C (= O) R 14, -N (R 10) C (= O) OR 14, -N (R 10 C (= O) NH 2, -N (R 10) C (= O) N (R 12) R 14, -N (R 10) C (= O) N (R 12) OR 14, -N (R 10 ) C (= S) NH 2 , -N (R 10 ) C (= S) N (R 12 ) R 14 , -N (R 10 ) S (= O) 2 R 14 , -N (R 10 ) S (= O) 2 NH 2 , -N (R 10) S (= O) 2 N (R 12) R 14, -C (= O) H, -C (= O) R 14, -C (= O) OH, —C (（O) OR 14 , —C (＝ O) NH 2 , —C (＝ O) N (R 12 ) R 14 , —C (＝ O) N (R 12 ) OR 14 , -C (R 15 ) = NOH or -C (R 15 ) = NOR 14 ,
R 6 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkyl group optionally substituted with R 7 , C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl group, C 2 -C 6 alkynyl group, C 2 -C 6 haloalkynyl group , -OH, C 1 ~ C 6 alkoxy group, C 1 ~ C 6 haloalkoxy group, C 1 ~ C 6 alkoxy group optionally substituted by R 7, C 2 ~ C 6 alkenyloxy group, C 2 ~ C 6 haloalkenyloxy group, C 2 ~ C 6 alkynyloxy group, C 2 ~ C 6 haloalkynyl group, C 3 ~ C 6 cycloalkyl group, C 3 ~ C 6 halocycloalkyl group, - H, C 1 ~ C 6 alkylthio group, C 1 ~ C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl, C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, C 2 -C 6 alkenylsulfonyl, C 2 -C 6 alkynylthio, C 2 -C 6 alkynylsulfinyl, C 2 ~ C 6 alkynylsulfonyl group, C 3 ~ C 6 cycloalkylthio group, C 3 ~ C 6 cycloalkyl alkylsulfinyl group, C 3 ~ C 6 cycloalkyl sulfonyl group, -NH 2, -N (R 12 ) R 14 , -N (R 10) C ( = O) H, -N (R 10) C (= O) R 14, -N (R 10) C (= O) OR 14, -N (R 10) C (= O) NH 2, -N (R 10) C (= O) N (R 12) R 14, -N (R 10) C (= O) N (R 12 ) OR 14 , —N (R 10 ) C (= S) NH 2 , —N (R 10 ) C (= S) N (R 12 ) R 14 , —N (R 10 ) S (= O) 2 R 14, -N (R 10) S (= O) 2 NH 2, -N (R 10) S (= O) 2 N (R 12) R 14, -N = C (R 12) R 14, -N = C (R 15 ) N (R 12 ) R 14 , -NHC (R 15 ) = NOR 14 , -N = S (R 14 ) R 12 , -N = S (= O) (R 14 ) R 12 , —N (R 10 ) NH 2 , —N (R 10 ) N (R 12 ) R 14 , —N (R 10 ) N (R 10 ) C (（O) H, —N (R 10 ) N (R 10 ) C (= O) R 14, -N (R 10) N (R 10) C (= O) OR 14, -N (R 10) N (R 10) S (= O) 2 R 14, -C (= O) H, - C (= O) R 14 , -C (R 15 ) = NOH, -C (R 15 ) = NOR 14 , -C (= O) OH, -C (= O) OR 14 , -C (= O) NH 2 or —C (＝ O) N (R 12 ) R 11
R 7 is a cyano group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —OH, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylthio group, a C 1 -C 6 Alkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, —C (＝ O) OH, —C (＝ O) OR 11 , —C (＝ O) NH 2 or —C (＝ O) N (R 12 ) R 11 represents
R 8 is a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —C (＝ O) OR 11 indicates -C (= O) NH 2 or -C (= O) N (R 12) R 11,
R 9 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 3 -C 6 cycloalkyl group, a —C (＝ O ) H, -C (= O) R 11 , -C (= O) OR 11 , -C (= O) NH 2 , -C (= O) N (R 12 ) R 11 or -S (= O) 2 R 11 ;
R 10 is a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 3 -C 6 cycloalkyl group, a —C (＝ O) R 11 , —C (＝ O) OR 11 or —S (＝ O) 2 R 11 , or R 9 and R 10 are mutually bonded to form a C 2 -C 6 alkylene bond Wherein the alkylene linkage may contain one oxygen, sulfur or nitrogen atom and the C 2 -C 6 alkylene linkage is monosubstituted by a halogen atom or a C 1 -C 6 alkyl group. Or may be poly-substituted,
R 11 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano C A 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or A C 3 -C 6 halocycloalkyl group;
R 12 is a hydrogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group , A C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group, or R 11 and R 12 are bonded to each other to form a C 2 -C 6 A 6 alkylene bond may be formed, wherein the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom, and the C 2 -C 6 alkylene bond is a halogen atom or a C 1 -C 6 alkyl group. May be mono-substituted or poly-substituted,
R 13 is a cyano group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —OH, —OR 14 , —OC (＝ O) R 14 , —OS (＝ O) 2 R 14, -OSi (R 14) 2 R 12, -SH, -SR 14, -S (= O) R 14, -S (= O) 2 R 14, -S (= O) 2 N (R 12) R 14 , —NH 2 , —N (R 12 ) R 14 , —N (R 10 ) C (＝ O) H, —N (R 10 ) C (＝ O) R 14 , —N (R 10 ) C (= O) OR 14 , -N (R 10 ) C (= O) NH 2 , -N (R 10 ) C (= O) N (R 12 ) R 14 , -N (R 10 ) C (= O ) N (R 12 ) OR 14 , —N (R 10 ) C (= S) NH 2 , —N (R 10 ) C (= S) N (R 12 ) R 14 , —N (R 10 ) S ( = O) 2 R 14, -N ( R 10) S (= O) 2 NH 2, -N (R 10) S (= O) 2 N (R 12) R 14, -C (= O) H, - C (= O) R 14 , -C (= O) OH, -C (= O) OR 14 , -C (= O) NH 2 , -C (= O) N (R 12 ) R 14 , -C (= S) NH 2 , —C (＝ S) N (R 12 ) R 14 , —C (R 15 ) = NOH, —C (R 15 ) = NOR 14 , —Si (R 14 ) 2 R 12 , A phenyl group, an aromatic heterocyclic ring or a saturated heterocyclic ring, which is unsubstituted or substituted by (Z) p 1 ,
R 14 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano C A 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, unsubstituted or substituted with (Z) p 1 phenyl group, unsubstituted or substituted with (Z) p 1 phenyl C 1 -C 6 alkyl group, aromatic heterocyclic ring Represents an aromatic heterocyclic C 1 -C 6 alkyl group, a saturated heterocyclic ring or a saturated heterocyclic C 1 -C 6 alkyl group, or R 12 and R 14 are mutually bonded to form C 2 -C 6 Alkylene bond May form, this time the alkylene bonded oxygen atom, may contain one sulfur atom or a nitrogen atom, and C 2 ~ C 6 alkylene linkage monosubstituted or by halogen atoms or C 1 ~ C 6 alkyl group May be poly-substituted,
R 15 represents a hydrogen atom, a halogen atom, —NH 2 , a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, Represents a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group, or R 14 and R 15 are each other May combine to form a C 2 -C 6 alkylene bond, wherein the alkylene bond may contain one oxygen, sulfur or nitrogen atom, and the C 2 -C 6 alkylene bond may be a halogen atom or May be mono- or poly-substituted by a C 1 -C 6 alkyl group,
Z is a halogen atom, cyano group, nitro group, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, —OH, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1 ~ C 6 alkylthio group, C 1 ~ C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group , —NH 2 , mono (C 1 -C 6 alkyl) amino group, di (C 1 -C 6 alkyl) amino group, C 1 -C 6 alkylcarbonylamino group, N- (C 1 -C 6 alkylcarbonyl) -N- (C 1 -C 6 alkyl) amino group, C 1 -C 6 alkoxycarbonylamino group, N- (C 1 -C 6 alkoxycarbonyl) -N- (C 1 -C 6- alkyl) amino group, C 1 -C 6 alkylsulfonylamino group, N- (C 1 -C 6 alkylsulfonyl) -N- (C 1 -C 6 alkyl) amino group, C 1 -C 6 haloalkylsulfonylamino group , N- (C 1 -C 6 haloalkylsulfonyl) -N- (C 1 -C 6 alkyl) amino group, —C (＝ O) NH 2 , mono (C 1 -C 6 alkyl) aminocarbonyl group, di ( A C 1 -C 6 alkyl) aminocarbonyl group, a mono (C 1 -C 6 haloalkyl) aminocarbonyl group or a phenyl group;
An aromatic heterocycle is
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000011
を示し、
　飽和複素環は、 Indicates that
A saturated heterocycle is
Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000012
を示し、
　ｐ１は、０～５の整数を示し、
　ｐ２は、０～４の整数を示し、
　ｐ３は、０～３の整数を示し、
　ｐ４は、０～２の整数を示し、
　ｔは、０又は１の整数を示す］
で表されることを特徴とする３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩。

（２）前記（１）に記載の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩を有効成分として含有する農薬組成物。
（３）農薬組成物が、さらに界面活性剤を含有する前記（２）に記載の農薬組成物。
（４）前記（１）に記載の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩を活性成分として含有する有害生物防除剤。
（５）有害生物防除剤が、殺虫剤、殺センチュウ剤及び殺ダニ剤である前記（４）に記載の有害生物防除剤。
（６）農園芸用植物を栽培する水田、畑地、芝地、果樹園、非農耕地、温室、育苗施設、植物工場における有害生物に対して、防除効力を有する前記（５）に記載の有害生物防除剤。
（７）農園芸用植物が、育種法又は遺伝子組換え技術により耐性を付与された植物である前記（６）に記載の有害生物防除剤。
（８）前記（１）に記載の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩の有効成分量を使用する有害生物の防除方法。
（９）前記（１）に記載の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩を有効成分として含有する農薬組成物を、農園芸用作物または農園芸用作物を生育させようとする若しくは生育している場所に対して、同時に又は分割して作用させることによる、有害生物の防除方法。
（１０）有害生物防除剤を施用する場所が、水田、畑地、芝地、果樹園、非農耕地、温室、育苗施設、植物工場である前記（８）又は（９）に記載の有害生物の防除方法。
（１１）前記（１）に記載の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体、又はその農業上許容される塩を殺虫剤、殺センチュウ剤及び殺ダニ剤として使用する前記（８）～（１０）のいずれかに記載の有害生物の防除方法。
（１２）前記（４）～（７）のいずれかに記載の有害生物防除剤を、農園芸用作物に対する有害生物を防除に使用する記載の有害生物防除剤の使用方法。
（１３）一般式［ＩＩ］ Indicates that
p 1 represents an integer of 0 to 5,
p 2 represents an integer of 0 to 4,
p 3 represents an integer of 0 to 3,
p 4 represents an integer of 0 to 2,
t represents an integer of 0 or 1]
A 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or an agriculturally acceptable salt thereof, represented by the formula:

(2) An agrochemical composition containing the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or the agriculturally acceptable salt thereof according to (1) as an active ingredient.
(3) The pesticidal composition according to (2), wherein the pesticidal composition further contains a surfactant.
(4) A pest control agent comprising the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or the agriculturally acceptable salt thereof according to the above (1) as an active ingredient.
(5) The pest control agent according to the above (4), wherein the pest control agent is an insecticide, a nematicide, and an acaricide.
(6) The harmful substance according to the above (5), which has a controlling effect on pests in paddy fields, fields, turf, orchards, non-agricultural lands, greenhouses, nursery facilities, and plant factories for cultivating agricultural and horticultural plants. Biocontrol agents.
(7) The pesticidal agent according to (6), wherein the agricultural or horticultural plant is a plant to which resistance has been imparted by a breeding method or a genetic recombination technique.
(8) Control of pests using the active ingredient of the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or the agriculturally acceptable salt thereof described in (1) above Method.
(9) An agricultural chemical composition comprising the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or the agriculturally acceptable salt thereof as an active ingredient according to (1), A method for controlling pests by simultaneously or separately acting on agricultural or horticultural crops or places where agricultural or horticultural crops are to be grown or are growing.
(10) The pest according to the above (8) or (9), wherein the place to which the pesticide is applied is a paddy field, a field, a lawn, an orchard, a non-agricultural land, a greenhouse, a nursery, or a plant factory. Control method.
(11) The 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or the agriculturally acceptable salt thereof according to the above (1) is used as an insecticide, nematocide and acaricide The method for controlling pests according to any of (8) to (10), which is used as an agent.
(12) A method for using the pest control agent according to any of (4) to (7), wherein the pest control agent is used for controlling pests on agricultural and horticultural crops.
(13) General formula [II]
Figure JPOXMLDOC01-appb-C000013
Figure JPOXMLDOC01-appb-C000013
　[式中、
　Ｋは、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、フェニルオキシ基又は無置換若しくは（Ｚ）ｐ１により置換されたフェニルＣ１～Ｃ６アルコキシ基を示し、
　Ｒ３は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、－ＮＨ２、－Ｎ（Ｒ９）Ｒ１０、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｓ）ＮＨ２を示し、
　ｎは、０～３の整数を示し、
　Ｒ４は、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、－ＮＨ２又は－Ｎ（Ｒ９）Ｒ１０を示し、
　Ｒ５は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｒ８によって任意に置換されたＣ３～Ｃ６シクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｒ１３によって任意に置換されたＣ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｒ１３によって任意に置換されたＣ２～Ｃ６アルキニル基、－ＯＨ、－ＯＳ（＝Ｏ）２Ｒ１４、－ＯＳｉ（Ｒ１４）２Ｒ１２、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルコキシ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルコキシ基、Ｃ２～Ｃ６アルケニルオキシ基、Ｃ２～Ｃ６ハロアルケニルオキシ基、Ｃ２～Ｃ６アルキニルオキシ基、Ｃ２～Ｃ６ハロアルキニルオキシ基、Ｃ３～Ｃ６シクロアルキルオキシ基、Ｃ３～Ｃ６ハロシクロアルキルオキシ基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルオキシ基、芳香族複素環オキシ基、飽和複素環オキシ基、－ＳＨ、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルチオ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルスルフィニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルスルホニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルチオ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルスルフィニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルスルホニル基、Ｃ２～Ｃ６アルケニルチオ基、Ｃ２～Ｃ６アルケニルスルフィニル基、Ｃ２～Ｃ６アルケニルスルホニル基、Ｃ２～Ｃ６ハロアルケニルチオ基、Ｃ２～Ｃ６ハロアルケニルスルフィニル基、Ｃ２～Ｃ６ハロアルケニルスルホニル基、Ｃ２～Ｃ６アルキニルチオ基、Ｃ２～Ｃ６アルキニルスルフィニル基、Ｃ２～Ｃ６アルキニルスルホニル基、Ｃ３～Ｃ６シクロアルキルチオ基、Ｃ３～Ｃ６シクロアルキルスルフィニル基、Ｃ３～Ｃ６シクロアルキルスルホニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルチオ基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルスルフィニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルスルホニル基、芳香族複素環チオ基、芳香族複素環スルフィニル基、芳香族複素環スルホニル基、飽和複素環チオ基、飽和複素環スルフィニル基、飽和複素環スルホニル基、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｃ（Ｒ１５）＝ＮＯＨ又は－Ｃ（Ｒ１５）＝ＮＯＲ１４を示し、
　Ｒ６は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルコキシ基、Ｃ２～Ｃ６アルケニルオキシ基、Ｃ２～Ｃ６ハロアルケニルオキシ基、Ｃ２～Ｃ６アルキニルオキシ基、Ｃ２～Ｃ６ハロアルキニルオキシ基、Ｃ３～Ｃ６シクロアルキルオキシ基、Ｃ３～Ｃ６ハロシクロアルキルオキシ基、－ＳＨ、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、Ｃ２～Ｃ６アルケニルチオ基、Ｃ２～Ｃ６アルケニルスルフィニル基、Ｃ２～Ｃ６アルケニルスルホニル基、Ｃ２～Ｃ６アルキニルチオ基、Ｃ２～Ｃ６アルキニルスルフィニル基、Ｃ２～Ｃ６アルキニルスルホニル基、Ｃ３～Ｃ６シクロアルキルチオ基、Ｃ３～Ｃ６シクロアルキルスルフィニル基、Ｃ３～Ｃ６シクロアルキルスルホニル基、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｎ＝Ｃ（Ｒ１２）Ｒ１４、－Ｎ＝Ｃ（Ｒ１５）Ｎ（Ｒ１２）Ｒ１４、－ＮＨＣ（Ｒ１５）＝ＮＯＲ１４、－Ｎ＝Ｓ（Ｒ１４）Ｒ１２、－Ｎ＝Ｓ（＝Ｏ）（Ｒ１４）Ｒ１２、－Ｎ（Ｒ１０）ＮＨ２、－Ｎ（Ｒ１０）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（Ｒ１５）＝ＮＯＨ、－Ｃ（Ｒ１５）＝ＮＯＲ１４、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
　Ｒ７は、シアノ基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
　Ｒ８は、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
　Ｒ９は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ３～Ｃ６シクロアルキル基、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１１、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１又は－Ｓ（＝Ｏ）２Ｒ１１を示し、
　Ｒ１０は、水素原子、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ３～Ｃ６シクロアルキル基、－Ｃ（＝Ｏ）Ｒ１１、－Ｃ（＝Ｏ）ＯＲ１１又は－Ｓ（＝Ｏ）２Ｒ１１を示すか、或いは、Ｒ９及びＲ１０は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
　Ｒ１１は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示し、
　Ｒ１２は、水素原子、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示すか、或いは、Ｒ１１及びＲ１２は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
　Ｒ１３は、シアノ基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－ＯＨ、－ＯＲ１４、－ＯＳ（＝Ｏ）２Ｒ１４、－ＯＳｉ（Ｒ１４）２Ｒ１２、－ＳＨ、－ＳＲ１４、－Ｓ（＝Ｏ）Ｒ１４、－Ｓ（＝Ｏ）２Ｒ１４、－Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｓ）ＮＨ２、－Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（Ｒ１５）＝ＮＯＨ、－Ｃ（Ｒ１５）＝ＮＯＲ１４、－Ｓｉ（Ｒ１４）２Ｒ１２、無置換若しくは（Ｚ）ｐ１により置換されたフェニル基、芳香族複素環又は飽和複素環を示し、
　Ｒ１４は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルＣ１～Ｃ６アルキル基、芳香族複素環、芳香族複素環Ｃ１～Ｃ６アルキル基、飽和複素環又は飽和複素環Ｃ１～Ｃ６アルキル基を示すか、或いは、Ｒ１２及びＲ１４は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
　Ｒ１５は、水素原子、ハロゲン原子、－ＮＨ２、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示すか、或いは、Ｒ１４及びＲ１５は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
　Ｚは、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、－ＮＨ２、モノ（Ｃ１～Ｃ６アルキル）アミノ基、ジ（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルキルカルボニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルキルカルボニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルコキシカルボニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルコキシカルボニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルキルスルホニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルキルスルホニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６ハロアルキルスルホニルアミノ基、Ｎ－（Ｃ１～Ｃ６ハロアルキルスルホニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、－Ｃ（＝Ｏ）ＮＨ２、モノ（Ｃ１～Ｃ６アルキル）アミノカルボニル基、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル基、モノ（Ｃ１～Ｃ６ハロアルキル）アミノカルボニル基又はフェニル基を示し、
　芳香族複素環は、 [Where,
K represents -OH, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkoxy group, a phenyloxy group or a phenyl C 1 -C 6 alkoxy group which is unsubstituted or substituted by (Z) p 1 ;
R 3 is a halogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylthio group, a C 1 -C 6 alkylsulfinyl group , C 1 -C 6 alkylsulfonyl group, —NH 2 , —N (R 9 ) R 10 , —C (＝ O) NH 2 or —C (＝ S) NH 2 ,
n represents an integer of 0 to 3,
R 4 is a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano group, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl Groups, C 2 -C 6 alkynyl groups, C 2 -C 6 haloalkynyl groups, —OH, C 1 -C 6 alkoxy groups, C 1 -C 6 haloalkoxy groups, C 1 -C 6 alkylthio groups, C 1- C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group, —NH 2 or —N (R 9 ) R 10 ,
R 5 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, C 1 ~ C 6 alkyl group, C 1 ~ C 6 haloalkyl group, C 1 ~ C 6 alkyl group optionally substituted by R 13, R 13 C 1 ~ C 6 haloalkyl group optionally substituted by, C 3 ~ C 6 cycloalkyl group, C 3 ~ C 6 halocycloalkyl group, C 3 ~ C 6 cycloalkyl group optionally substituted by R 8, C 2 ~ C 6 alkenyl group, C 2 ~ C 6 haloalkenyl group, C 2 ~ C 6 alkenyl group optionally substituted by R 13, C 2 ~ C 6 alkynyl group, C 2 ~ C 6 haloalkynyl group, C 2 ~ C 6 alkynyl group optionally substituted by R 13, -OH, -OS (= O) 2 R 14, -OSi (R 14) 2 R 12, C 1 ~ C 6 alkoxy group, C 1 ~ 6 haloalkoxy group, C 1 ~ C 6 alkoxy group optionally substituted by R 13, C 1 ~ C 6 haloalkoxy group optionally substituted by R 13, C 2 ~ C 6 alkenyloxy group, C 2 ~ C 6 haloalkenyloxy group, C 2 -C 6 alkynyloxy group, C 2 -C 6 haloalkynyloxy group, C 3 -C 6 cycloalkyloxy group, C 3 -C 6 halocycloalkyloxy group, unsubstituted or (Z) phenyloxy group, aromatic heterocyclic oxy group, saturated heterocyclic oxy group, —SH, C 1 -C 6 alkylthio group, C 1 -C 6 alkylsulfinyl group, C 1 -C substituted by p 1 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group C 1 ~ C 6 alkylthio group optionally substituted by R 13, C 1 ~ C 6 alkylsulfinyl optionally substituted by R 13 sulfinyl group, C 1 ~ C 6 alkylsulfonyl group optionally substituted by R 13, C 1 ~ C 6 haloalkylthio group optionally substituted by R 13, C 1 ~ C 6 haloalkylsulfenyl optionally substituted by R 13 sulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group optionally substituted by R 13 , C 2 ~ C 6 alkenylthio group, C 2 ~ C 6 alkenylsulfinyl group, C 2 ~ C 6 alkenyl sulfonyl group, C 2 ~ C 6 haloalkenyl two thio group, C 2 ~ C 6 halo alkenylsulfinyl group, C 2 ~ C 6 haloalkenyl sulfonyl group, C 2 ~ C 6 alkynylthio, C 2 ~ C 6 alkynyl Rufiniru group, C 2 ~ C 6 alkynyl-sulfonyl group, C 3 ~ C 6 cycloalkylthio group, C 3 ~ C 6 cycloalkyl alkylsulfinyl group, C 3 ~ C 6 cycloalkyl sulfonyl group, the unsubstituted or (Z) p 1 Substituted phenylthio group, unsubstituted or substituted by (Z) p 1 phenylsulfinyl group, unsubstituted or substituted by (Z) p 1 phenylsulfonyl group, aromatic heterocyclic thio group, aromatic heterocyclic sulfinyl Group, aromatic heterocyclic sulfonyl group, saturated heterocyclic thio group, saturated heterocyclic sulfinyl group, saturated heterocyclic sulfonyl group, -NH 2 , -N (R 12 ) R 14 , -N (R 10 ) C (= O ) H, -N (R 10) C (= O) R 14, -N (R 10) C (= O) OR 14, -N (R 10) C (= O) NH 2, - (R 10) C (= O ) N (R 12) R 14, -N (R 10) C (= O) N (R 12) OR 14, -N (R 10) C (= S) NH 2, -N (R 10) C (= S) N (R 12) R 14, -N (R 10) S (= O) 2 R 14, -N (R 10) S (= O) 2 NH 2, - N (R 10) S (= O) 2 N (R 12) R 14, -C (= O) H, -C (= O) R 14, -C (= O) NH 2, -C (= O ) N (R 12 ) R 14 , —C (＝ O) N (R 12 ) OR 14 , —C (R 15 ) = NOH or —C (R 15 ) = NOR 14
R 6 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkyl group optionally substituted with R 7 , C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl group, C 2 -C 6 alkynyl group, C 2 -C 6 haloalkynyl group , -OH, C 1 ~ C 6 alkoxy group, C 1 ~ C 6 haloalkoxy group, C 1 ~ C 6 alkoxy group optionally substituted by R 7, C 2 ~ C 6 alkenyloxy group, C 2 ~ C 6 haloalkenyloxy group, C 2 ~ C 6 alkynyloxy group, C 2 ~ C 6 haloalkynyl group, C 3 ~ C 6 cycloalkyl group, C 3 ~ C 6 halocycloalkyl group, - H, C 1 ~ C 6 alkylthio group, C 1 ~ C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl, C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, C 2 -C 6 alkenylsulfonyl, C 2 -C 6 alkynylthio, C 2 -C 6 alkynylsulfinyl, C 2 ~ C 6 alkynylsulfonyl group, C 3 ~ C 6 cycloalkylthio group, C 3 ~ C 6 cycloalkyl alkylsulfinyl group, C 3 ~ C 6 cycloalkyl sulfonyl group, -NH 2, -N (R 12 ) R 14 , -N (R 10) C ( = O) H, -N (R 10) C (= O) R 14, -N (R 10) C (= O) OR 14, -N (R 10) C (= O) NH 2, -N (R 10) C (= O) N (R 12) R 14, -N (R 10) C (= O) N (R 12 ) OR 14 , —N (R 10 ) C (= S) NH 2 , —N (R 10 ) C (= S) N (R 12 ) R 14 , —N (R 10 ) S (= O) 2 R 14, -N (R 10) S (= O) 2 NH 2, -N (R 10) S (= O) 2 N (R 12) R 14, -N = C (R 12) R 14, -N = C (R 15 ) N (R 12 ) R 14 , -NHC (R 15 ) = NOR 14 , -N = S (R 14 ) R 12 , -N = S (= O) (R 14 ) R 12 , —N (R 10 ) NH 2 , —N (R 10 ) N (R 12 ) R 14 , —N (R 10 ) N (R 10 ) C (（O) H, —N (R 10 ) N (R 10 ) C (= O) R 14, -N (R 10) N (R 10) C (= O) OR 14, -N (R 10) N (R 10) S (= O) 2 R 14, -C (= O) H, - C (＝ O) R 14 , —C (R 15 ) = NOH, —C (R 15 ) = NOR 14 , —C (＝ O) NH 2 or —C (＝ O) N (R 12 ) R 11 Show,
R 7 is a cyano group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —OH, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylthio group, a C 1 -C 6 An alkylsulfinyl group, a C 1 -C 6 alkylsulfonyl group, —C (＝ O) NH 2 or —C (＝ O) N (R 12 ) R 11 ,
R 8 is a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —C (＝ O) NH 2 Or —C (＝ O) N (R 12 ) R 11 ;
R 9 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 3 -C 6 cycloalkyl group, a —C (＝ O ) H, -C (= O) R 11 , -C (= O) OR 11 , -C (= O) NH 2 , -C (= O) N (R 12 ) R 11 or -S (= O) 2 R 11 ;
R 10 is a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 3 -C 6 cycloalkyl group, a —C (＝ O) R 11 , —C (＝ O) OR 11 or —S (＝ O) 2 R 11 , or R 9 and R 10 are mutually bonded to form a C 2 -C 6 alkylene bond Wherein the alkylene linkage may contain one oxygen, sulfur or nitrogen atom and the C 2 -C 6 alkylene linkage is monosubstituted by a halogen atom or a C 1 -C 6 alkyl group. Or may be poly-substituted,
R 11 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano C A 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or A C 3 -C 6 halocycloalkyl group;
R 12 is a hydrogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group , A C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group, or R 11 and R 12 are bonded to each other to form a C 2 -C 6 A 6 alkylene bond may be formed, wherein the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom, and the C 2 -C 6 alkylene bond is a halogen atom or a C 1 -C 6 alkyl group. May be mono-substituted or poly-substituted,
R 13 is a cyano group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —OH, —OR 14 , —OS (＝ O) 2 R 14 , —OSi (R 14 ) 2 R 12 , -SH, -SR 14 , -S (= O) R 14 , -S (= O) 2 R 14 , -S (= O) 2 N (R 12 ) R 14 , -NH 2 , -N (R 12 ) R 14 , —N (R 10 ) C (＝ O) H, —N (R 10 ) C (＝ O) R 14 , —N (R 10 ) C (＝ O) OR 14 , —N (R 10 ) C (＝ O) NH 2 , —N (R 10 ) C (＝ O) N (R 12 ) R 14 , —N (R 10 ) C (＝ O) N (R 12 ) OR 14 , -N (R 10 ) C (= S) NH 2 , -N (R 10 ) C (= S) N (R 12 ) R 14 , -N (R 10 ) S (= O) 2 R 14 , -N ( 10) S (= O) 2 NH 2, -N (R 10) S (= O) 2 N (R 12) R 14, -C (= O) H, -C (= O) R 14, -C (= O) NH 2 , -C (= O) N (R 12 ) R 14 , -C (= S) NH 2 , -C (= S) N (R 12 ) R 14 , -C (R 15 ) ＮＯNOH, —C (R 15 ) ＮＯNOR 14 , —Si (R 14 ) 2 R 12 , a phenyl group, an aromatic heterocyclic ring or a saturated heterocyclic ring, which is unsubstituted or substituted by (Z) p 1 ,
R 14 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano C A 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, unsubstituted or substituted with (Z) p 1 phenyl group, unsubstituted or substituted with (Z) p 1 phenyl C 1 -C 6 alkyl group, aromatic heterocyclic ring Represents an aromatic heterocyclic C 1 -C 6 alkyl group, a saturated heterocyclic ring or a saturated heterocyclic C 1 -C 6 alkyl group, or R 12 and R 14 are mutually bonded to form C 2 -C 6 Alkylene bond May form, this time the alkylene bonded oxygen atom, may contain one sulfur atom or a nitrogen atom, and C 2 ~ C 6 alkylene linkage monosubstituted or by halogen atoms or C 1 ~ C 6 alkyl group May be poly-substituted,
R 15 represents a hydrogen atom, a halogen atom, —NH 2 , a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, Represents a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group, or R 14 and R 15 are each other May combine to form a C 2 -C 6 alkylene bond, wherein the alkylene bond may contain one oxygen, sulfur or nitrogen atom, and the C 2 -C 6 alkylene bond may be a halogen atom or May be mono- or poly-substituted by a C 1 -C 6 alkyl group,
Z is a halogen atom, cyano group, nitro group, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, —OH, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1 ~ C 6 alkylthio group, C 1 ~ C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group , —NH 2 , mono (C 1 -C 6 alkyl) amino group, di (C 1 -C 6 alkyl) amino group, C 1 -C 6 alkylcarbonylamino group, N- (C 1 -C 6 alkylcarbonyl) -N- (C 1 -C 6 alkyl) amino group, C 1 -C 6 alkoxycarbonylamino group, N- (C 1 -C 6 alkoxycarbonyl) -N- (C 1 -C 6- alkyl) amino group, C 1 -C 6 alkylsulfonylamino group, N- (C 1 -C 6 alkylsulfonyl) -N- (C 1 -C 6 alkyl) amino group, C 1 -C 6 haloalkylsulfonylamino group , N- (C 1 -C 6 haloalkylsulfonyl) -N- (C 1 -C 6 alkyl) amino group, —C (＝ O) NH 2 , mono (C 1 -C 6 alkyl) aminocarbonyl group, di ( A C 1 -C 6 alkyl) aminocarbonyl group, a mono (C 1 -C 6 haloalkyl) aminocarbonyl group or a phenyl group;
An aromatic heterocycle is
Figure JPOXMLDOC01-appb-C000014
Figure JPOXMLDOC01-appb-C000014
を示し、
　飽和複素環は、 Indicates that
A saturated heterocycle is
Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000015
を示し、
　ｐ１は、０～５の整数を示し、
　ｐ２は、０～４の整数を示し、
　ｐ３は、０～３の整数を示し、
　ｐ４は、０～２の整数を示し、
　ｔは、０又は１の整数を示す］
で表されることを特徴とする３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸誘導体又はその塩。
（１４）一般式［ＩＩＩ］ Indicates that
p 1 represents an integer of 0 to 5,
p 2 represents an integer of 0 to 4,
p 3 represents an integer of 0 to 3,
p 4 represents an integer of 0 to 2,
t represents an integer of 0 or 1]
A 3- (1H-1,2,4-triazol-1-yl) benzoic acid derivative or a salt thereof, which is represented by the following formula:
(14) General formula [III]
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000016
　[式中、
　Ｗは、水素原子、ハロゲン原子又はシアノ基を示し、
　Ｒ３は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、－ＮＨ２、－Ｎ（Ｒ９）Ｒ１０、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｓ）ＮＨ２を示し、
　ｎは、０～３の整数を示し、
　Ｒ４は、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、－ＮＨ２又は－Ｎ（Ｒ９）Ｒ１０を示し、
　Ｒ５は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｒ８によって任意に置換されたＣ３～Ｃ６シクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｒ１３によって任意に置換されたＣ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｒ１３によって任意に置換されたＣ２～Ｃ６アルキニル基、－ＯＨ、－ＯＣ（＝Ｏ）Ｒ１４、－ＯＳ（＝Ｏ）２Ｒ１４、－ＯＳｉ（Ｒ１４）２Ｒ１２、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルコキシ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルコキシ基、Ｃ２～Ｃ６アルケニルオキシ基、Ｃ２～Ｃ６ハロアルケニルオキシ基、Ｃ２～Ｃ６アルキニルオキシ基、Ｃ２～Ｃ６ハロアルキニルオキシ基、Ｃ３～Ｃ６シクロアルキルオキシ基、Ｃ３～Ｃ６ハロシクロアルキルオキシ基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルオキシ基、芳香族複素環オキシ基、飽和複素環オキシ基、－ＳＨ、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルチオ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルスルフィニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルスルホニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルチオ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルスルフィニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルスルホニル基、Ｃ２～Ｃ６アルケニルチオ基、Ｃ２～Ｃ６アルケニルスルフィニル基、Ｃ２～Ｃ６アルケニルスルホニル基、Ｃ２～Ｃ６ハロアルケニルチオ基、Ｃ２～Ｃ６ハロアルケニルスルフィニル基、Ｃ２～Ｃ６ハロアルケニルスルホニル基、Ｃ２～Ｃ６アルキニルチオ基、Ｃ２～Ｃ６アルキニルスルフィニル基、Ｃ２～Ｃ６アルキニルスルホニル基、Ｃ３～Ｃ６シクロアルキルチオ基、Ｃ３～Ｃ６シクロアルキルスルフィニル基、Ｃ３～Ｃ６シクロアルキルスルホニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルチオ基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルスルフィニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルスルホニル基、芳香族複素環チオ基、芳香族複素環スルフィニル基、芳香族複素環スルホニル基、飽和複素環チオ基、飽和複素環スルフィニル基、飽和複素環スルホニル基、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１４、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｃ（Ｒ１５）＝ＮＯＨ又は－Ｃ（Ｒ１５）＝ＮＯＲ１４を示し、
　Ｒ６は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルコキシ基、Ｃ２～Ｃ６アルケニルオキシ基、Ｃ２～Ｃ６ハロアルケニルオキシ基、Ｃ２～Ｃ６アルキニルオキシ基、Ｃ２～Ｃ６ハロアルキニルオキシ基、Ｃ３～Ｃ６シクロアルキルオキシ基、Ｃ３～Ｃ６ハロシクロアルキルオキシ基、－ＳＨ、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、Ｃ２～Ｃ６アルケニルチオ基、Ｃ２～Ｃ６アルケニルスルフィニル基、Ｃ２～Ｃ６アルケニルスルホニル基、Ｃ２～Ｃ６アルキニルチオ基、Ｃ２～Ｃ６アルキニルスルフィニル基、Ｃ２～Ｃ６アルキニルスルホニル基、Ｃ３～Ｃ６シクロアルキルチオ基、Ｃ３～Ｃ６シクロアルキルスルフィニル基、Ｃ３～Ｃ６シクロアルキルスルホニル基、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｎ＝Ｃ（Ｒ１２）Ｒ１４、－Ｎ＝Ｃ（Ｒ１５）Ｎ（Ｒ１２）Ｒ１４、－ＮＨＣ（Ｒ１５）＝ＮＯＲ１４、－Ｎ＝Ｓ（Ｒ１４）Ｒ１２、－Ｎ＝Ｓ（＝Ｏ）（Ｒ１４）Ｒ１２、－Ｎ（Ｒ１０）ＮＨ２、－Ｎ（Ｒ１０）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（Ｒ１５）＝ＮＯＨ、－Ｃ（Ｒ１５）＝ＮＯＲ１４、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１４、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
　Ｒ７は、シアノ基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
　Ｒ８は、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
　Ｒ９は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ３～Ｃ６シクロアルキル基、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１１、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１又は－Ｓ（＝Ｏ）２Ｒ１１を示し、
　Ｒ１０は、水素原子、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ３～Ｃ６シクロアルキル基、－Ｃ（＝Ｏ）Ｒ１１、－Ｃ（＝Ｏ）ＯＲ１１又は－Ｓ（＝Ｏ）２Ｒ１１を示すか、或いは、Ｒ９及びＲ１０は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
　Ｒ１１は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示し、
　Ｒ１２は、水素原子、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示すか、或いは、Ｒ１１及びＲ１２は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
　Ｒ１３は、シアノ基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－ＯＨ、－ＯＲ１４、－ＯＣ（＝Ｏ）Ｒ１４、－ＯＳ（＝Ｏ）２Ｒ１４、－ＯＳｉ（Ｒ１４）２Ｒ１２、－ＳＨ、－ＳＲ１４、－Ｓ（＝Ｏ）Ｒ１４、－Ｓ（＝Ｏ）２Ｒ１４、－Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１４、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｓ）ＮＨ２、－Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（Ｒ１５）＝ＮＯＨ、－Ｃ（Ｒ１５）＝ＮＯＲ１４、－Ｓｉ（Ｒ１４）２Ｒ１２、無置換若しくは（Ｚ）ｐ１により置換されたフェニル基、芳香族複素環又は飽和複素環を示し、
　Ｒ１４は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルＣ１～Ｃ６アルキル基、芳香族複素環、芳香族複素環Ｃ１～Ｃ６アルキル基、飽和複素環又は飽和複素環Ｃ１～Ｃ６アルキル基を示すか、或いは、Ｒ１２及びＲ１４は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
　Ｒ１５は、水素原子、ハロゲン原子、－ＮＨ２、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示すか、或いは、Ｒ１４及びＲ１５は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
　Ｚは、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、－ＮＨ２、モノ（Ｃ１～Ｃ６アルキル）アミノ基、ジ（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルキルカルボニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルキルカルボニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルコキシカルボニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルコキシカルボニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルキルスルホニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルキルスルホニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６ハロアルキルスルホニルアミノ基、Ｎ－（Ｃ１～Ｃ６ハロアルキルスルホニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、－Ｃ（＝Ｏ）ＮＨ２、モノ（Ｃ１～Ｃ６アルキル）アミノカルボニル基、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル基、モノ（Ｃ１～Ｃ６ハロアルキル）アミノカルボニル基又はフェニル基を示し、
　芳香族複素環は、 [Where,
W represents a hydrogen atom, a halogen atom or a cyano group,
R 3 is a halogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylthio group, a C 1 -C 6 alkylsulfinyl group , C 1 -C 6 alkylsulfonyl group, —NH 2 , —N (R 9 ) R 10 , —C (＝ O) NH 2 or —C (＝ S) NH 2 ,
n represents an integer of 0 to 3,
R 4 is a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano group, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl Groups, C 2 -C 6 alkynyl groups, C 2 -C 6 haloalkynyl groups, —OH, C 1 -C 6 alkoxy groups, C 1 -C 6 haloalkoxy groups, C 1 -C 6 alkylthio groups, C 1- C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group, —NH 2 or —N (R 9 ) R 10 ,
R 5 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, C 1 ~ C 6 alkyl group, C 1 ~ C 6 haloalkyl group, C 1 ~ C 6 alkyl group optionally substituted by R 13, R 13 C 1 ~ C 6 haloalkyl group optionally substituted by, C 3 ~ C 6 cycloalkyl group, C 3 ~ C 6 halocycloalkyl group, C 3 ~ C 6 cycloalkyl group optionally substituted by R 8, C 2 ~ C 6 alkenyl group, C 2 ~ C 6 haloalkenyl group, C 2 ~ C 6 alkenyl group optionally substituted by R 13, C 2 ~ C 6 alkynyl group, C 2 ~ C 6 haloalkynyl group, A C 2 -C 6 alkynyl group optionally substituted with R 13 , —OH, —OC (＝ O) R 14 , —OS (＝ O) 2 R 14 , —OSi (R 14 ) 2 R 12 , C 1 ~ C Alkoxy group, C 1 ~ C 6 haloalkoxy group, C 1 ~ C 6 alkoxy group optionally substituted by R 13, C 1 ~ C 6 haloalkoxy group optionally substituted by R 13, C 2 ~ C 6 Alkenyloxy group, C 2 -C 6 haloalkenyloxy group, C 2 -C 6 alkynyloxy group, C 2 -C 6 haloalkynyloxy group, C 3 -C 6 cycloalkyloxy group, C 3 -C 6 halocyclo Alkyloxy group, unsubstituted or substituted by (Z) p 1 phenyloxy group, aromatic heterocyclic oxy group, saturated heterocyclic oxy group, —SH, C 1 -C 6 alkylthio group, C 1 -C 6 alkyl sulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 B alkylsulfonyl group, C 1 ~ C 6 alkylthio group optionally substituted by R 13, C which is optionally substituted by R 13 1 ~ C 6 alkylsulfinyl group, C 1 ~ C which is optionally substituted by R 13 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group optionally substituted by R 13, C 1 ~ C 6 haloalkylsulfenyl optionally substituted by R 13 sulfinyl group, C 1 ~ optionally substituted by R 13 C 6 haloalkylsulfonyl group, C 2 ~ C 6 alkenylthio group, C 2 ~ C 6 alkenylsulfinyl group, C 2 ~ C 6 alkenyl sulfonyl group, C 2 ~ C 6 haloalkenyl two thio group, C 2 ~ C 6 haloalkenyl A sulfinyl group, a C 2 -C 6 haloalkenylsulfonyl group, a C 2 -C 6 alkynylthio group, C 2 ~ C 6 alkynylsulfinyl group, C 2 ~ C 6 alkynyl-sulfonyl group, C 3 ~ C 6 cycloalkylthio group, C 3 ~ C 6 cycloalkyl alkylsulfinyl group, C 3 ~ C 6 cycloalkyl alkylsulfonyl group, an unsubstituted or (Z) phenylthio group substituted by p 1, an unsubstituted or (Z) phenyl sulfinyl group substituted by p 1, an unsubstituted or (Z) phenylsulfonyl group substituted by p 1, an aromatic heterocyclic thio group An aromatic heterocyclic sulfinyl group, an aromatic heterocyclic sulfonyl group, a saturated heterocyclic thio group, a saturated heterocyclic sulfinyl group, a saturated heterocyclic sulfonyl group, -NH 2 , -N (R 12 ) R 14 , -N (R 10) C (= O) H , -N (R 10) C (= O) R 14, -N (R 10) C (= O) OR 14, -N (R 10 C (= O) NH 2, -N (R 10) C (= O) N (R 12) R 14, -N (R 10) C (= O) N (R 12) OR 14, -N (R 10 ) C (= S) NH 2 , -N (R 10 ) C (= S) N (R 12 ) R 14 , -N (R 10 ) S (= O) 2 R 14 , -N (R 10 ) S (= O) 2 NH 2 , -N (R 10) S (= O) 2 N (R 12) R 14, -C (= O) H, -C (= O) R 14, -C (= O) OH, —C (（O) OR 14 , —C (＝ O) NH 2 , —C (＝ O) N (R 12 ) R 14 , —C (＝ O) N (R 12 ) OR 14 , -C (R 15 ) = NOH or -C (R 15 ) = NOR 14 ,
R 6 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkyl group optionally substituted with R 7 , C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl group, C 2 -C 6 alkynyl group, C 2 -C 6 haloalkynyl group , -OH, C 1 ~ C 6 alkoxy group, C 1 ~ C 6 haloalkoxy group, C 1 ~ C 6 alkoxy group optionally substituted by R 7, C 2 ~ C 6 alkenyloxy group, C 2 ~ C 6 haloalkenyloxy group, C 2 ~ C 6 alkynyloxy group, C 2 ~ C 6 haloalkynyl group, C 3 ~ C 6 cycloalkyl group, C 3 ~ C 6 halocycloalkyl group, - H, C 1 ~ C 6 alkylthio group, C 1 ~ C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl, C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, C 2 -C 6 alkenylsulfonyl, C 2 -C 6 alkynylthio, C 2 -C 6 alkynylsulfinyl, C 2 ~ C 6 alkynylsulfonyl group, C 3 ~ C 6 cycloalkylthio group, C 3 ~ C 6 cycloalkyl alkylsulfinyl group, C 3 ~ C 6 cycloalkyl sulfonyl group, -NH 2, -N (R 12 ) R 14 , -N (R 10) C ( = O) H, -N (R 10) C (= O) R 14, -N (R 10) C (= O) OR 14, -N (R 10) C (= O) NH 2, -N (R 10) C (= O) N (R 12) R 14, -N (R 10) C (= O) N (R 12 ) OR 14 , —N (R 10 ) C (= S) NH 2 , —N (R 10 ) C (= S) N (R 12 ) R 14 , —N (R 10 ) S (= O) 2 R 14, -N (R 10) S (= O) 2 NH 2, -N (R 10) S (= O) 2 N (R 12) R 14, -N = C (R 12) R 14, -N = C (R 15 ) N (R 12 ) R 14 , -NHC (R 15 ) = NOR 14 , -N = S (R 14 ) R 12 , -N = S (= O) (R 14 ) R 12 , —N (R 10 ) NH 2 , —N (R 10 ) N (R 12 ) R 14 , —N (R 10 ) N (R 10 ) C (（O) H, —N (R 10 ) N (R 10 ) C (= O) R 14, -N (R 10) N (R 10) C (= O) OR 14, -N (R 10) N (R 10) S (= O) 2 R 14, -C (= O) H, - C (= O) R 14 , -C (R 15 ) = NOH, -C (R 15 ) = NOR 14 , -C (= O) OH, -C (= O) OR 14 , -C (= O) NH 2 or —C (＝ O) N (R 12 ) R 11
R 7 is a cyano group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —OH, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylthio group, a C 1 -C 6 Alkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, —C (＝ O) OH, —C (＝ O) OR 11 , —C (＝ O) NH 2 or —C (＝ O) N (R 12 ) R 11 represents
R 8 is a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —C (＝ O) OR 11 indicates -C (= O) NH 2 or -C (= O) N (R 12) R 11,
R 9 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 3 -C 6 cycloalkyl group, a —C (＝ O ) H, -C (= O) R 11 , -C (= O) OR 11 , -C (= O) NH 2 , -C (= O) N (R 12 ) R 11 or -S (= O) 2 R 11 ;
R 10 is a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 3 -C 6 cycloalkyl group, a —C (＝ O) R 11 , —C (＝ O) OR 11 or —S (＝ O) 2 R 11 , or R 9 and R 10 are mutually bonded to form a C 2 -C 6 alkylene bond Wherein the alkylene linkage may contain one oxygen, sulfur or nitrogen atom and the C 2 -C 6 alkylene linkage is monosubstituted by a halogen atom or a C 1 -C 6 alkyl group. Or may be poly-substituted,
R 11 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano C A 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or A C 3 -C 6 halocycloalkyl group;
R 12 is a hydrogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group , A C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group, or R 11 and R 12 are bonded to each other to form a C 2 -C 6 A 6 alkylene bond may be formed, wherein the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom, and the C 2 -C 6 alkylene bond is a halogen atom or a C 1 -C 6 alkyl group. May be mono-substituted or poly-substituted,
R 13 is a cyano group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —OH, —OR 14 , —OC (＝ O) R 14 , —OS (＝ O) 2 R 14, -OSi (R 14) 2 R 12, -SH, -SR 14, -S (= O) R 14, -S (= O) 2 R 14, -S (= O) 2 N (R 12) R 14 , —NH 2 , —N (R 12 ) R 14 , —N (R 10 ) C (＝ O) H, —N (R 10 ) C (＝ O) R 14 , —N (R 10 ) C (= O) OR 14 , -N (R 10 ) C (= O) NH 2 , -N (R 10 ) C (= O) N (R 12 ) R 14 , -N (R 10 ) C (= O ) N (R 12 ) OR 14 , —N (R 10 ) C (= S) NH 2 , —N (R 10 ) C (= S) N (R 12 ) R 14 , —N (R 10 ) S ( = O) 2 R 14, -N ( R 10) S (= O) 2 NH 2, -N (R 10) S (= O) 2 N (R 12) R 14, -C (= O) H, - C (= O) R 14 , -C (= O) OH, -C (= O) OR 14 , -C (= O) NH 2 , -C (= O) N (R 12 ) R 14 , -C (= S) NH 2 , —C (＝ S) N (R 12 ) R 14 , —C (R 15 ) = NOH, —C (R 15 ) = NOR 14 , —Si (R 14 ) 2 R 12 , A phenyl group, an aromatic heterocyclic ring or a saturated heterocyclic ring, which is unsubstituted or substituted by (Z) p 1 ,
R 14 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano C A 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, unsubstituted or substituted with (Z) p 1 phenyl group, unsubstituted or substituted with (Z) p 1 phenyl C 1 -C 6 alkyl group, aromatic heterocyclic ring Represents an aromatic heterocyclic C 1 -C 6 alkyl group, a saturated heterocyclic ring or a saturated heterocyclic C 1 -C 6 alkyl group, or R 12 and R 14 are mutually bonded to form C 2 -C 6 Alkylene bond May form, this time the alkylene bonded oxygen atom, may contain one sulfur atom or a nitrogen atom, and C 2 ~ C 6 alkylene linkage monosubstituted or by halogen atoms or C 1 ~ C 6 alkyl group May be poly-substituted,
R 15 represents a hydrogen atom, a halogen atom, —NH 2 , a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, Represents a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group, or R 14 and R 15 are each other May combine to form a C 2 -C 6 alkylene bond, wherein the alkylene bond may contain one oxygen, sulfur or nitrogen atom, and the C 2 -C 6 alkylene bond may be a halogen atom or May be mono- or poly-substituted by a C 1 -C 6 alkyl group,
Z is a halogen atom, cyano group, nitro group, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, —OH, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1 ~ C 6 alkylthio group, C 1 ~ C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group , —NH 2 , mono (C 1 -C 6 alkyl) amino group, di (C 1 -C 6 alkyl) amino group, C 1 -C 6 alkylcarbonylamino group, N- (C 1 -C 6 alkylcarbonyl) -N- (C 1 -C 6 alkyl) amino group, C 1 -C 6 alkoxycarbonylamino group, N- (C 1 -C 6 alkoxycarbonyl) -N- (C 1 -C 6- alkyl) amino group, C 1 -C 6 alkylsulfonylamino group, N- (C 1 -C 6 alkylsulfonyl) -N- (C 1 -C 6 alkyl) amino group, C 1 -C 6 haloalkylsulfonylamino group , N- (C 1 -C 6 haloalkylsulfonyl) -N- (C 1 -C 6 alkyl) amino group, —C (＝ O) NH 2 , mono (C 1 -C 6 alkyl) aminocarbonyl group, di ( A C 1 -C 6 alkyl) aminocarbonyl group, a mono (C 1 -C 6 haloalkyl) aminocarbonyl group or a phenyl group;
An aromatic heterocycle is
Figure JPOXMLDOC01-appb-C000017
Figure JPOXMLDOC01-appb-C000017
を示し、
　飽和複素環は、 Indicates that
A saturated heterocycle is
Figure JPOXMLDOC01-appb-C000018
Figure JPOXMLDOC01-appb-C000018
を示し、
　ｐ１は、０～５の整数を示し、
　ｐ２は、０～４の整数を示し、
　ｐ３は、０～３の整数を示し、
　ｐ４は、０～２の整数を示し、
　ｔは、０又は１の整数を示す］
で表されることを特徴とする１－フェニル－１Ｈ－１，２，４－トリアゾール誘導体又はその塩。
（１６）前記（１５）に記載の１－フェニル－１Ｈ－１，２，４－トリアゾール誘導体又はその塩を原料とすることを特徴とする、前記（１）に記載の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体の製造方法。 Indicates that
p 1 represents an integer of 0 to 5,
p 2 represents an integer of 0 to 4,
p 3 represents an integer of 0 to 3,
p 4 represents an integer of 0 to 2,
t represents an integer of 0 or 1]
A 1-phenyl-1H-1,2,4-triazole derivative or a salt thereof, which is represented by the following formula:
(16) The 3- (1H-1) according to (1), wherein the 1-phenyl-1H-1,2,4-triazole derivative or the salt thereof according to (15) is used as a raw material. , 2,4-triazol-1-yl) benzoic acid amide derivatives.
　本発明の一般式［Ｉ］で表される化合物は、優れた有害生物防除作用を有し、カメムシ目害虫、チョウ目害虫、コウチュウ目害虫、ハエ目害虫、ハチ目害虫、バッタ目害虫、アザミウマ目害虫、ハダニ類、植物寄生性線虫類等の広範囲の有害生物に対して優れた防除効果を示し、又、薬剤抵抗性を獲得した有害生物をも防除することができる。　 The compound represented by the general formula [I] of the present invention has an excellent pest control effect, and includes stink bugs, lepidoptera, pests, flies, pests, wasps, thrips, and thrips. It shows an excellent control effect on a wide range of pests such as eye pests, spider mites and plant parasitic nematodes, and can also control pests that have acquired drug resistance.
　特に、本発明の化合物を含有する有害生物防除剤は、ナミハダニ、カンザワハダニ、ミカンハダニ等に代表されるハダニ類、トビイロウンカ、ツマグロヨコバイ、ワタアブラムシ等に代表されるカメムシ目害虫、イネミズゾウムシ、ドロオイムシ、コガネムシ等に代表されるコウチュウ目害虫、サツマイモネコブセンチュウ等の線虫類、及びコナガ、ニカメイガ、オオタバコガ等に代表されるチョウ目害虫に卓効を示す。また、浸透移行性に優れるため、土壌処理による安全かつ省力的施用方法が可能である。 In particular, pest control agents containing the compound of the present invention, spider mites, spider mites, Mandarin spider mites, spider mites, etc .; It is highly effective against nematodes such as representatives of the order Lepidoptera and root-knot nematodes, and insects of the order Lepidoptera such as Japanese moth, P. persica, and Tobacco. In addition, because of its excellent permeability, a safe and labor-saving application method by soil treatment is possible.
　本明細書に記載された記号及び用語について説明する。 記号 The symbols and terms described in this specification will be described.
　本発明において、「有害生物防除剤」とは、農園芸分野、家畜及びペット等の動物、家庭用或いは防疫用の殺虫剤、殺ダニ剤、殺センチュウ剤等を意味する。 に お い て In the present invention, the term “pesticide” means animals such as agricultural and horticultural fields, livestock and pets, and insecticides, acaricides, nematocides, etc. for domestic or epidemic control.
　本発明において、「ハロゲン原子」とは、フッ素原子、塩素原子、臭素原子、ヨウ素原子を示す。
　本発明において、「Ｃ１～Ｃ６」等の表記は、元素記号に続く数字が炭素数を表し、例えば、この場合では炭素数が１～６個の範囲のいずれかでよいことを示している。
　本発明において、「Ｃ１～Ｃ６アルキル基」とは、特に限定しない限り、炭素数が１～６の直鎖又は分岐鎖状のアルキル基を示し、例えばメチル、エチル、ｎ－プロピル、イソプロピル、ｎ－ブチル、ｓｅｃ－ブチル、イソブチル、ｔｅｒｔ－ブチル、ｎ－ペンチル、１－メチルブチル、２－メチルブチル、３－メチルブチル、１－エチルプロピル、１，１－ジメチルプロピル、１，２－ジメチルプロピル、ネオペンチル、ｎ－へキシル、１－メチルペンチル、２－メチルペンチル、３－メチルペンチル、４－メチルペンチル、１－エチルブチル、２－エチルブチル、１，１－ジメチルブチル、１，２－ジメチルブチル、１，３－ジメチルブチル、２，２－ジメチルブチル、２，３－ジメチルブチル、３，３－ジメチルブチル、１，１，２－トリメチルプロピル、１，２，２－トリメチルプロピル、１－エチル－１－メチルプロピル又は１－エチル－２－メチルプロピル等の基を挙げることができる。 In the present invention, “halogen atom” refers to a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
In the present invention, the notation such as “C 1 -C 6 ” indicates that the number following the element symbol indicates the number of carbon atoms. For example, in this case, the number of carbon atoms may be any of 1 to 6 I have.
In the present invention, the “C 1 -C 6 alkyl group” refers to a linear or branched alkyl group having 1 to 6 carbon atoms, unless otherwise specified. For example, methyl, ethyl, n-propyl, isopropyl , N-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, Neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 2,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2 Trimethylpropyl, 1,2,2-trimethyl propyl, mention may be made of 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl and the like groups.
　本発明において、「Ｃ１～Ｃ６ハロアルキル基」とは、特に限定しない限り、同一又は相異なる１～１３のハロゲン原子で置換されている炭素数が１～６の直鎖又は分岐鎖状のハロアルキル基を示し、例えば、フルオロメチル、ジフルオロメチル、トリフルオロメチル、クロロメチル、ジクロロメチル、トリクロロメチル、ブロモメチル、ジブロモメチル、トリブロモメチル、ヨードメチル、クロロジフルオロメチル、ジクロロフルオロメチル、１－フルオロエチル、２－フルオロエチル、１，１－ジフルオロエチル、２，２－ジフルオロエチル、２，２，２－トリフルオロエチル、１，１，２，２－テトラフルオロエチル、ペンタフルオロエチル、１－クロロエチル、２－クロロエチル、１，１－ジクロロエチル、２，２－ジクロロエチル、２，２，２－トリクロロエチル、１，１，２，２－テトラクロロエチル、ペンタクロロエチル、１－ブロモエチル、２－ブロモエチル、２，２，２－トリブロモエチル、１－ヨードエチル、２－ヨードエチル、２－クロロ－２，２－ジフルオロエチル、２，２－ジクロロ－２－フルオロエチル、２－トリクロロエチル、１－フルオロプロピル、２－フルオロプロピル、３－フルオロプロピル、１，１－ジフルオロプロピル、２，２－ジフルオロプロピル、３，３－ジフルオロプロピル、３，３，３－トリフルオロプロピル、２，２，３，３，３－ペンタフルオロプロピル、ヘプタフルオロプロピル、１－フルオロプロパン－２－イル、２－フルオロプロパン－２－イル、１，１－ジフルオロプロパン－２－イル、１，２－ジフルオロプロパン－２－イル、１，３－ジフルオロプロパン－２－イル、１，２，３－トリフルオロプロパン－２－イル、１，１，３，３－テトラフルオロプロパン－２－イル、１，１，１，３，３，３－ヘキサフルオロプロパン－２－イル、ヘプタフルオロプロパン－２－イル、１－クロロプロピル、２－クロロプロピル、３－クロロプロピル、１，１－ジクロロプロピル、２，２－ジクロロプロピル、３，３－ジクロロプロピル、３，３，３－トリクロロプロピル、２，２，３，３，３－ペンタクロロプロピル、ヘプタクロロプロピル、１－クロロプロパン－２－イル、２－クロロプロパン－２－イル、１，１－ジクロロプロパン－２－イル、１，２－ジクロロプロパン－２－イル、１，３－ジクロロプロパン－２－イル、１，２，３－トリクロロプロパン－２－イル、１，１，３，３－テトラクロロプロパン－２－イル、１，１，１，３，３，３－ヘキサクロロプロパン－２－イル、ヘプタクロロプロパン－２－イル、１－ブロモプロピル、２－ブロモプロピル、３－ブロモプロピル、１－ブロモプロパン－２－イル、２－ブロモプロパン－２－イル、１－ヨードプロピル、２－ヨードプロピル、３－ヨードプロピル、１－ヨードプロパン－２－イル、２－ヨードプロパン－２－イル、１－フルオロブチル、２－フルオロブチル、３－フルオロブチル、４－フルオロブチル、４，４－ジフルオロブチル、４，４，４－トリフルオロブチル、３，３，４，４，４－ペンタフルオロブチル、２，２，３，３，４，４，４－ヘプタフルオロブチル、ノナフルオロブチル、１，１，１－トリフルオロブタン－２－イル、４，４，４－トリフルオロブタン－２－イル、３，３，４，４，４－ペンタフルオロブタン－２－イル、ノナフルオロブタン－２－イル、１，１，１，３，３，３－ヘキサフルオロ－２－（トリフルオロメチル）プロパン－２－イル、１－クロロブチル、２－クロロブチル、３－クロロブチル、４－クロロブチル、４，４－ジクロロブチル、４，４，４－トリクロロブチル、ノナクロロブチル、１，１，１－トリクロロブタン－２－イル、４，４，４－トリクロロブタン－２－イル、ノナクロロブタン－２－イル、１－ブロモブチル、２－ブロモブチル、３－ブロモブチル、４－ブロモブチル、１－ヨードブチル、２－ヨードブチル、３－ヨードブチル、４－ヨードブチル、４－クロロ－１，１，２，２，３，３，４，４－オクタフルオロブチル、４－ブロモ－１，１，２，２，３，３，４，４－オクタフルオロブチル、１－フルオロペンチル、２－フルオロペンチル、３－フルオロペンチル、４－フルオロペンチル、５－フルオロペンチル、５，５，５－トリフルオロペンチル、４，４，５，５，５－ペンタフルオロペンチル、３，３，４，４，５，５，５－ヘプタフルオロペンチル、２，２，３，３，４，４，５，５，５－ノナフルオロペンチル、ウンデカフルオロペンチル、１－クロロペンチル、２－クロロペンチル、３－クロロペンチル、４－クロロペンチル、５－クロロペンチル、５，５，５－トリクロロペンチル、４，４，５，５，５－ペンタクロロペンチル、３，３，４，４，５，５，５－ヘプタクロロペンチル、２，２，３，３，４，４，５，５，５－ノナクロロペンチル、ウンデカクロロペンチル、１－ブロモペンチル、２－ブロモペンチル、３－ブロモペンチル、４－ブロモペンチル、５－ブロモペンチル、５－ヨードペンチル、１－フルオロヘキシル、２－フルオロヘキシル、３－フルオロヘキシル、４－フルオロヘキシル、５－フルオロヘキシル、６－フルオロヘキシル、６，６，６－トリフルオロヘキシル、５，５，６，６，６－ペンタフルオロヘキシル、４，４，５，５，６，６，６－ヘプタフルオロヘキシル、３，３，４，４，５，５，６，６，６－ノナフルオロヘキシル、２，２，３，３，４，４，５，５，６，６，６－ウンデカフルオロヘキシル、トリデカフルオロヘキシル、１－クロロヘキシル、２－クロロヘキシル、３－クロロヘキシル、４－クロロヘキシル、５－クロロヘキシル、６－クロロヘキシル、５－ブロモヘキシル、６－ブロモヘキシル、５－ヨードヘキシル又は６－ヨードヘキシル等の基を挙げることができる。 In the present invention, “C 1 -C 6 haloalkyl group” means a straight-chain or branched-chain C 1 -C 6 substituted with 1 to 13 halogen atoms which are the same or different, unless otherwise specified. Represents a haloalkyl group, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, iodomethyl, chlorodifluoromethyl, dichlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1-chloroethyl, 2 -Chloroethyl, 1,1-dichloroethyl, 2,2-dichloroethyl , 2,2,2-trichloroethyl, 1,1,2,2-tetrachloroethyl, pentachloroethyl, 1-bromoethyl, 2-bromoethyl, 2,2,2-tribromoethyl, 1-iodoethyl, 2-iodoethyl , 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2-trichloroethyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-fluoropropan-2-yl , 2-fluoropropan-2-yl, 1,1-difluoropropan-2-yl, 1,2-difluoropro 2-yl, 1,3-difluoropropan-2-yl, 1,2,3-trifluoropropan-2-yl, 1,1,3,3-tetrafluoropropan-2-yl, 1,1 1,1,3,3,3-hexafluoropropan-2-yl, heptafluoropropan-2-yl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 1,1-dichloropropyl, 2,2 -Dichloropropyl, 3,3-dichloropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentachloropropyl, heptachloropropyl, 1-chloropropan-2-yl, 2-chloropropane- 2-yl, 1,1-dichloropropan-2-yl, 1,2-dichloropropan-2-yl, 1,3-dichloropropan-2-yl, 1,2,3-trichloroprop Pan-2-yl, 1,1,3,3-tetrachloropropan-2-yl, 1,1,1,3,3,3-hexachloropropan-2-yl, heptachloropropan-2-yl, 1-bromo Propyl, 2-bromopropyl, 3-bromopropyl, 1-bromopropan-2-yl, 2-bromopropan-2-yl, 1-iodopropyl, 2-iodopropyl, 3-iodopropyl, 1-iodopropane- 2-yl, 2-iodopropan-2-yl, 1-fluorobutyl, 2-fluorobutyl, 3-fluorobutyl, 4-fluorobutyl, 4,4-difluorobutyl, 4,4,4-trifluorobutyl, 3,3,4,4,4-pentafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl, 1,1,1-trifluoro Tan-2-yl, 4,4,4-trifluorobutan-2-yl, 3,3,4,4,4-pentafluorobutan-2-yl, nonafluorobutan-2-yl, 1,1, 1,3,3,3-hexafluoro-2- (trifluoromethyl) propan-2-yl, 1-chlorobutyl, 2-chlorobutyl, 3-chlorobutyl, 4-chlorobutyl, 4,4-dichlorobutyl, 4,4 , 4-trichlorobutyl, nonachlorobutyl, 1,1,1-trichlorobutan-2-yl, 4,4,4-trichlorobutan-2-yl, nonachlorobutan-2-yl, 1-bromobutyl, 2-bromobutyl, 3-bromobutyl, 4-bromobutyl, 1-iodobutyl, 2-iodobutyl, 3-iodobutyl, 4-iodobutyl, 4-chloro-1,1,2,2,3,3,4,4 Octafluorobutyl, 4-bromo-1,1,2,2,3,3,4,4-octafluorobutyl, 1-fluoropentyl, 2-fluoropentyl, 3-fluoropentyl, 4-fluoropentyl, 5- Fluoropentyl, 5,5,5-trifluoropentyl, 4,4,5,5,5-pentafluoropentyl, 3,3,4,4,5,5,5-heptafluoropentyl, 2,2,3 , 3,4,4,5,5,5-nonafluoropentyl, undecafluoropentyl, 1-chloropentyl, 2-chloropentyl, 3-chloropentyl, 4-chloropentyl, 5-chloropentyl, 5,5 , 5-Trichloropentyl, 4,4,5,5,5-pentachloropentyl, 3,3,4,4,5,5,5-heptachloropentyl, 2,2,3,3,4,4 5,5 , 5-Nonachloropentyl, undecachloropentyl, 1-bromopentyl, 2-bromopentyl, 3-bromopentyl, 4-bromopentyl, 5-bromopentyl, 5-iodopentyl, 1-fluorohexyl, 2-fluoro Hexyl, 3-fluorohexyl, 4-fluorohexyl, 5-fluorohexyl, 6-fluorohexyl, 6,6,6-trifluorohexyl, 5,5,6,6,6-pentafluorohexyl, 4,4 5,5,6,6,6-heptafluorohexyl, 3,3,4,4,5,5,6,6,6-nonafluorohexyl, 2,2,3,3,4,4,5 5,6,6,6-undecafluorohexyl, tridecafluorohexyl, 1-chlorohexyl, 2-chlorohexyl, 3-chlorohexyl, 4-chlorohexyl, - chlorohexyl, 6-chloro-hexyl, 5-bromo-hexyl, 6-bromo-hexyl, 5-iodo-hexyl or 6-iodo groups hexyl.
　本発明において、「Ｃ３～Ｃ６シクロアルキル基」とは、特に限定しない限り、炭素数が３～６のシクロアルキル基を示し、例えばシクロプロピル、シクロブチル、シクロペンチル又はシクロヘキシル等の基を挙げることができる。 In the present invention, “C 3 -C 6 cycloalkyl group” refers to a cycloalkyl group having 3 to 6 carbon atoms unless otherwise specified, and examples thereof include groups such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Can be.
　本発明において、「Ｃ３～Ｃ６ハロシクロアルキル基」とは、特に限定しない限り、同一又は相異なる１～１１のハロゲン原子で置換されている炭素数が３～６のシクロアルキル基を示し、例えば１－フルオロシクロプロピル、２－フルオロシクロプロピル、２，２－ジフルオロシクロプロピル、２，２，３，３－テトラフルオロシクロプロピル、１－クロロシクロプロピル、２－クロロシクロプロピル、２，２－ジクロロシクロプロピル、２，２，３，３－テトラクロロシクロプロピル、２，２－ジブロモシクロプロピル、２，２－ジヨードシクロプロピル、１－フルオロシクロブチル、２－フルオロシクロブチル、３－フルオロシクロブチル、３，３－ジフルオロシクロブチル、ヘプタフルオロシクロブチル、２－クロロシクロブチル、３－クロロシクロブチル、３，３－ジクロロシクロブチル、３，３－ジブロモシクロブチル、３，３－ジヨードシクロブチル、１－フルオロシクロペンチル、２－フルオロシクロペンチル、３－フルオロシクロペンチル、２，２－ジフルオロシクロペンチル、３，３－ジフルオロシクロペンチル、ノナフルオロシクロペンチル、２，２－ジクロロシクロペンチル、３，３－ジクロロシクロペンチル、２，２－ジブロモシクロペンチル、３，３－ジブロモシクロペンチル、２，２－ジヨードシクロペンチル、３，３－ジヨードシクロペンチル、１－フルオロシクロヘキシル、２－フルオロシクロヘキシル、３－フルオロシクロヘキシル、４－フルオロシクロヘキシル、２，２－ジフルオロシクロヘキシル、３，３－ジフルオロシクロヘキシル、４，４－ジフルオロシクロヘキシル、１－クロロシクロヘキシル、２－クロロシクロヘキシル、３－クロロシクロヘキシル、４－クロロシクロヘキシル、２，２－ジクロロシクロヘキシル、３，３－ジクロロシクロヘキシル、４，４－ジクロロシクロヘキシル、３，３－ジブロモシクロヘキシル、４，４－ジブロモシクロヘキシル、３，３－ジヨードシクロヘキシル又は４，４－ジヨードシクロヘキシル等の基を挙げることができる。 In the present invention, the “C 3 -C 6 halocycloalkyl group” refers to a cycloalkyl group having 3 to 6 carbon atoms, which is substituted with the same or different 1 to 11 halogen atoms, unless otherwise specified. For example, 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 1-chlorocyclopropyl, 2-chlorocyclopropyl, 2,2 -Dichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-diiodocyclopropyl, 1-fluorocyclobutyl, 2-fluorocyclobutyl, 3-fluoro Cyclobutyl, 3,3-difluorocyclobutyl, heptafluorocyclobutyl, 2-chlorocyclobutyl 3-chlorocyclobutyl, 3,3-dichlorocyclobutyl, 3,3-dibromocyclobutyl, 3,3-diiodocyclobutyl, 1-fluorocyclopentyl, 2-fluorocyclopentyl, 3-fluorocyclopentyl, 2,2- Difluorocyclopentyl, 3,3-difluorocyclopentyl, nonafluorocyclopentyl, 2,2-dichlorocyclopentyl, 3,3-dichlorocyclopentyl, 2,2-dibromocyclopentyl, 3,3-dibromocyclopentyl, 2,2-diiodocyclopentyl, 3,3-diiodocyclopentyl, 1-fluorocyclohexyl, 2-fluorocyclohexyl, 3-fluorocyclohexyl, 4-fluorocyclohexyl, 2,2-difluorocyclohexyl, 3,3-difluorocyclohexyl 4,4-difluorocyclohexyl, 1-chlorocyclohexyl, 2-chlorocyclohexyl, 3-chlorocyclohexyl, 4-chlorocyclohexyl, 2,2-dichlorocyclohexyl, 3,3-dichlorocyclohexyl, 4,4-dichlorocyclohexyl, 3, Examples include groups such as 3-dibromocyclohexyl, 4,4-dibromocyclohexyl, 3,3-diiodocyclohexyl, and 4,4-diiodocyclohexyl.
　本発明において、「Ｃ２～Ｃ６アルケニル基」とは、特に限定しない限り、炭素数が２～６の直鎖又は分岐鎖状のアルケニル基を示し、例えばビニル、１－プロペニル、イソプロペニル、２－プロペニル、１－ブテニル、１－メチル－１－プロペニル、２－ブテニル、１－メチル－２－プロペニル、３－ブテニル、２－メチル－１－プロペニル、２－メチル－２－プロペニル、１，３－ブタジエニル、１－ペンテニル、１－エチル－２－プロペニル、２－ペンテニル、１－メチル－１－ブテニル、３－ペンテニル、１－メチル－２－ブテニル、４－ペンテニル、１－メチル－３－ブテニル、３－メチル－１－ブテニル、１，２－ジメチル－２－プロペニル、１，１－ジメチル－２－プロペニル、２－メチル－２－ブテニル、３－メチル－２－ブテニル、１，２－ジメチル－１－プロペニル、２－メチル－３－ブテニル、３－メチル－３－ブテニル、１，３－ペンタジエニル、１－ビニル－２－プロペニル、１－ヘキセニル、１－プロピル－２－プロペニル、２－へキセニル、１－メチル－１－ペンテニル、１－エチル－２－ブテニル、３－ヘキセニル、４－ヘキセニル、５－ヘキセニル、１－メチル－４－ペンテニル、１－エチル－３－ブテニル、１－(イソブチル)ビニル、１－エチル－１－メチル－２－プロペニル、１－エチル－２－メチル－２－プロペニル、１－(イソプロピル)－２－プロペニル、２－メチル－２－ペンテニル、３－メチル－３－ペンテニル、４－メチル－３－ペンテニル、１，３－ジメチル－２－ブテニル、１，１－ジメチル－３－ブテニル、３－メチル－４－ペンテニル、４－メチル－４－ペンテニル、１，２－ジメチル－３－ブテニル、１，３－ジメチル－３－ブテニル、１，１，２－トリメチル－２－プロペニル、１，５－ヘキサジエニル、１－ビニル－３－ブテニル又は２，４－ヘキサジエニル等の基を挙げることができる。 In the present invention, “C 2 -C 6 alkenyl group” refers to a linear or branched alkenyl group having 2 to 6 carbon atoms unless otherwise specified, and examples thereof include vinyl, 1-propenyl, isopropenyl, 2-propenyl, 1-butenyl, 1-methyl-1-propenyl, 2-butenyl, 1-methyl-2-propenyl, 3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1, 3-butadienyl, 1-pentenyl, 1-ethyl-2-propenyl, 2-pentenyl, 1-methyl-1-butenyl, 3-pentenyl, 1-methyl-2-butenyl, 4-pentenyl, 1-methyl-3- Butenyl, 3-methyl-1-butenyl, 1,2-dimethyl-2-propenyl, 1,1-dimethyl-2-propenyl, 2-methyl-2-butenyl, 3-methyl-2 Butenyl, 1,2-dimethyl-1-propenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,3-pentadienyl, 1-vinyl-2-propenyl, 1-hexenyl, 1-propyl- 2-propenyl, 2-hexenyl, 1-methyl-1-pentenyl, 1-ethyl-2-butenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-4-pentenyl, 1-ethyl-3 -Butenyl, 1- (isobutyl) vinyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-2-propenyl, 1- (isopropyl) -2-propenyl, 2-methyl-2- Pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1,3-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 3-methyl- -Pentenyl, 4-methyl-4-pentenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1,5-hexadienyl, 1 And groups such as -vinyl-3-butenyl or 2,4-hexadienyl.
　本発明において、「Ｃ２～Ｃ６ハロアルケニル基」とは、特に限定しない限り、同一又は相異なる１～１１のハロゲン原子で置換されている炭素数が２～６の直鎖又は分岐鎖状のアルケニル基を示し、例えば１－フルオロビニル、２－フルオロビニル、１，２－ジフルオロビニル、２，２－ジフルオロビニル、トリフルオロビニル、１－クロロビニル、２－クロロビニル、１，２－ジクロロビニル、２，２－ジクロロビニル、トリクロロビニル、１，２－ジブロモビニル、２，２－ジブロモビニル、トリブロモビニル、１，２－ジヨードモビニル、２，２－ジヨードビニル、トリヨードビニル、１－フルオロ－２－プロペニル、２－フルオロ－２－プロペニル、３－フルオロ－２－プロペニル、２，３－ジフルオロ－２－プロペニル、３，３－ジフルオロ－２－プロペニル、３，３－ジフルオロ－１－プロペニル、２，３，３－トリフルオロ－２－プロペニル、３，３，３－トリフルオロ－１－プロペニル、２－クロロ－３，３，３－トリフルオロ－１－プロペニル、１，２，３，３，３－ペンタフルオロ－１－プロペニル、１－クロロ－２－プロペニル、２－クロロ－２－プロペニル、３－クロロ－２－プロペニル、２，３－ジクロロ－２－プロペニル、３，３－ジクロロ－２－プロペニル、３，３－ジクロロ－１－プロペニル、２，３，３－トリクロロ－２－プロペニル、３，３，３－トリクロロ－１－プロペニル、３－ブロモ－２－プロペニル、３，３－ジブロモ－２－プロペニル、３，３－ジヨード－２－プロペニル、２，２－ジフルオロ－１－プロペン－２－イル、３，３，３－トリフルオロ－１－プロペン－２－イル、３，３，３－トリクロロ－１－プロペン－２－イル、４－フルオロ－３－ブテニル、４，４－ジフルオロ－３－ブテニル、４，４－ジフルオロ－３－ブテン－２－イル、４，４，４－トリフルオロ－２－ブテニル、３，４，４－トリフルオロ－３－ブテニル、２－トリフルオロメチル－２－プロペニル、２－トリフルオロメチル－３，３－ジフルオロ－２－プロペニル、４，４，４－トリフルオロ－３－クロロ－２－ブテニル、４，４－ジクロロ－３－ブテニル、４，４，４－トリクロロ－２－ブテニル、２－トリクロロメチル－２－プロペニル、５，５－ジフルオロ－４－ペンテニル、４，５，５－トリフルオロ－４－ペンテニル、５，５，５－トリフルオロ－３－ペンテニル、４，４，４－トリフルオロ－３－メチル－２－ブテニル、４，４，４－トリフルオロ－３－トリフルオロメチル－２－ブテニル、５，５－ジクロロ－４－ペンテニル、４，４，４－トリクロロ－３－メチル－２－ブテニル、６，６－ジフルオロ－５－ヘキセニル、５，６，６－トリフルオロ－５－ペンテニル、６，６，６－トリフルオロ－４－ペンテニル、５，５，５－トリフルオロ－４－メチル－３－ペンテニル、５，５，５－トリフルオロ－４－トリフルオロメチル－３－ペンテニル、６，６－ジクロロ－５－ヘキセニル又は５，５，５－トリクロロ－４－メチル－３－ペンテニル等の基を挙げることができる。 In the present invention, the term “C 2 -C 6 haloalkenyl group” means a linear or branched C 2 -C 6 substituted with 1 to 11 halogen atoms, which is the same or different, unless otherwise specified. And represents, for example, 1-fluorovinyl, 2-fluorovinyl, 1,2-difluorovinyl, 2,2-difluorovinyl, trifluorovinyl, 1-chlorovinyl, 2-chlorovinyl, 1,2-dichloro Vinyl, 2,2-dichlorovinyl, trichlorovinyl, 1,2-dibromovinyl, 2,2-dibromovinyl, tribromovinyl, 1,2-diiodomovinyl, 2,2-diiodovinyl, triiodovinyl, 1-fluoro- 2-propenyl, 2-fluoro-2-propenyl, 3-fluoro-2-propenyl, 2,3-difluoro-2-propenyl, 3, -Difluoro-2-propenyl, 3,3-difluoro-1-propenyl, 2,3,3-trifluoro-2-propenyl, 3,3,3-trifluoro-1-propenyl, 2-chloro-3,3 1,3-trifluoro-1-propenyl, 1,2,3,3,3-pentafluoro-1-propenyl, 1-chloro-2-propenyl, 2-chloro-2-propenyl, 3-chloro-2-propenyl 2,3-dichloro-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dichloro-1-propenyl, 2,3,3-trichloro-2-propenyl, 3,3,3-trichloro -1-propenyl, 3-bromo-2-propenyl, 3,3-dibromo-2-propenyl, 3,3-diiodo-2-propenyl, 2,2-difluoro-1-propen-2-yl, 3,3-trifluoro-1-propen-2-yl, 3,3,3-trichloro-1-propen-2-yl, 4-fluoro-3-butenyl, 4,4-difluoro-3-butenyl, , 4-Difluoro-3-buten-2-yl, 4,4,4-trifluoro-2-butenyl, 3,4,4-trifluoro-3-butenyl, 2-trifluoromethyl-2-propenyl, 2 -Trifluoromethyl-3,3-difluoro-2-propenyl, 4,4,4-trifluoro-3-chloro-2-butenyl, 4,4-dichloro-3-butenyl, 4,4,4-trichloro- 2-butenyl, 2-trichloromethyl-2-propenyl, 5,5-difluoro-4-pentenyl, 4,5,5-trifluoro-4-pentenyl, 5,5,5-trifluoro-3-pentenyl, , 4, 4-trifluoro-3-methyl-2-butenyl, 4,4,4-trifluoro-3-trifluoromethyl-2-butenyl, 5,5-dichloro-4-pentenyl, 4,4,4-trichloro- 3-methyl-2-butenyl, 6,6-difluoro-5-hexenyl, 5,6,6-trifluoro-5-pentenyl, 6,6,6-trifluoro-4-pentenyl, 5,5,5- Trifluoro-4-methyl-3-pentenyl, 5,5,5-trifluoro-4-trifluoromethyl-3-pentenyl, 6,6-dichloro-5-hexenyl or 5,5,5-trichloro-4- And groups such as methyl-3-pentenyl.
　本発明において、「Ｃ２～Ｃ６アルキニル基」とは、特に限定しない限り、炭素数が２～６の直鎖又は分岐鎖状のアルキニル基を示し、例えばエチニル、１－プロピニル、２－プロピニル、１－ブチニル、１－メチル－２－プロピニル、２－ブチニル、３－ブチニル、１－ペンチニル、１－エチル－２－プロピニル、２－ペンチニル、３－ペンチニル、１－メチル－２－ブチニル、４－ペンチニル、１－メチル－３－ブチニル、２－メチル－３－ブチニル、１－ヘキシニル、１－(ｎ－プロピル)－２－プロピニル、２－ヘキシニル、１－エチル－２－ブチニル、３－ヘキシニル、１－メチル－２－ペンチニル、１－メチル－３－ペンチニル、４－メチル－１－ペンチニル、３－メチル－１－ペンチニル、５－ヘキシニル、１－エチル－３－ブチニル、１－エチル－１－メチル－２－プロピニル、１－(イソプロピル)－２－プロピニル、１，１－ジメチル－２－ブチニル又は２，２－ジメチル－３－ブチニル等の基を挙げることができる。 In the present invention, “C 2 -C 6 alkynyl group” means a linear or branched alkynyl group having 2 to 6 carbon atoms, unless otherwise specified. , 1-butynyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-ethyl-2-propynyl, 2-pentynyl, 3-pentynyl, 1-methyl-2-butynyl, 4 -Pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-hexynyl, 1- (n-propyl) -2-propynyl, 2-hexynyl, 1-ethyl-2-butynyl, 3-hexynyl , 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 4-methyl-1-pentynyl, 3-methyl-1-pentynyl, 5-hexynyl, 1-ethyl-3- Groups such as tinyl, 1-ethyl-1-methyl-2-propynyl, 1- (isopropyl) -2-propynyl, 1,1-dimethyl-2-butynyl and 2,2-dimethyl-3-butynyl; it can.
　本発明において、「Ｃ２～Ｃ６ハロアルキニル基」とは、特に限定しない限り、同一又は相異なる１～９のハロゲン原子で置換されている炭素数が２～６の直鎖又は分岐鎖状のアルキニル基を示し、例えばフルオロエチニル、クロロエチニル、ブロモエチニル、ヨードエチニル、３－フルオロ－２－プロピニル、３－クロロ－２－プロピニル、３－ブロモ－２－プロピニル、３－ヨード－２－プロピニル、４－フルオロ－３－ブチニル、４－クロロ－３－ブチニル、４－ブロモ－３－ブチニル、４－ヨード－３－ブチニル、４，４－ジフルオロ－２－ブチニル、４，４－ジクロロ－２－ブチニル、４，４，４－トリフルオロ－２－ブチニル、４，４，４－トリクロロ－２－ブチニル、３－フルオロ－１－メチル－２－プロピニル、３－クロロ－１－メチル－２－プロピニル、５－フルオロ－４－ペンチニル、５－クロロ－４－ペンチニル、５，５，５－トリフルオロ－３－ペンチニル、５，５，５－トリクロロ－３－ペンチニル、４－フルオロ－２－メチル－３－ブチニル、４－クロロ－２－メチル－３－ブチニル、６－フルオロ－５－ヘキシニル、６－クロロ－５－ヘキシニル、６，６，６－トリフルオロ－４－ヘキシニル、６，６，６－トリクロロ－４－ヘキシニル、５－フルオロ－３－メチル－４－ペンチニル又は５－クロロ－３－メチル－４－ペンチニル等の基を挙げることができる。 In the present invention, “C 2 -C 6 haloalkynyl group” means a straight-chain or branched-chain having 2 to 6 carbon atoms substituted with the same or different 1 to 9 halogen atoms, unless otherwise specified. And represents, for example, fluoroethynyl, chloroethynyl, bromoethynyl, iodoethynyl, 3-fluoro-2-propynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 3-iodo-2-propynyl , 4-fluoro-3-butynyl, 4-chloro-3-butynyl, 4-bromo-3-butynyl, 4-iodo-3-butynyl, 4,4-difluoro-2-butynyl, 4,4-dichloro-2 -Butynyl, 4,4,4-trifluoro-2-butynyl, 4,4,4-trichloro-2-butynyl, 3-fluoro-1-methyl-2-propynyl, 3-chloro -1-methyl-2-propynyl, 5-fluoro-4-pentynyl, 5-chloro-4-pentynyl, 5,5,5-trifluoro-3-pentynyl, 5,5,5-trichloro-3-pentynyl, 4-fluoro-2-methyl-3-butynyl, 4-chloro-2-methyl-3-butynyl, 6-fluoro-5-hexynyl, 6-chloro-5-hexynyl, 6,6,6-trifluoro-4 Examples include -hexynyl, 6,6,6-trichloro-4-hexynyl, 5-fluoro-3-methyl-4-pentynyl and 5-chloro-3-methyl-4-pentynyl.
　本発明において、「Ｃ１～Ｃ６アルコキシ基」とは、特に限定しない限り、アルキル部分が上記の意味である（Ｃ１～Ｃ６アルキル）－Ｏ－基を示し、例えばメトキシ、エトキシ、ｎ－プロポキシ、イソプロポキシ、ｎ－ブトキシ、イソブトキシ、ｓｅｃ－ブトキシ、ｔｅｒｔ－ブトキシ、ｎ－ペントキシ、１－メチルブトキシ、２－メチルブトキシ、３－メチルブトキシ、１－エチルプロポキシ、１，１－ジメチルプロポキシ、１，２－ジメチルプロポキシ又はｎ－へキシルオキシ等の基を挙げることができる。 In the present invention, “C 1 -C 6 alkoxy group” means a (C 1 -C 6 alkyl) —O— group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified, and includes, for example, methoxy, ethoxy, n -Propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy , 1,2-dimethylpropoxy or n-hexyloxy.
　本発明において、「Ｃ１～Ｃ６ハロアルコキシ基」とは、特に限定しない限り、ハロアルキル部分が上記の意味である（Ｃ１～Ｃ６ハロアルキル）－Ｏ－基を示し、例えばジフルオロメトキシ、ジクロロメトキシ、トリフルオロメトキシ、トリクロロメトキシ、トリブロモメトキシ、クロロジフルオロメトキシ、ブロモジフルオロメトキシ、２－フルオロエトキシ、１－クロロエトキシ、２－クロロエトキシ、１－ブロモエトキシ、２－ブロモエトキシ、２，２－ジフルオロエトキシ、１，２－ジクロロエトキシ、２，２－ジクロロエトキシ、２，２，２－トリフルオロエトキシ、２，２，２－トリクロロエトキシ、１，１，２，２－テトラフルオロエトキシ、ペンタフルオロエトキシ、２－ブロモ－２－クロロエトキシ、２－クロロ－１，１，２，２－テトラフルオロエトキシ、１－クロロ－１，２，２，２－テトラフルオロエトキシ、１－クロロプロポキシ、２－クロロプロポキシ、３－クロロプロポキシ、２－ブロモプロポキシ、３－ブロモプロポキシ、２－ブロモ－１－メチルエトキシ、３－ヨードプロポキシ、２，３－ジクロロプロポキシ、２，３－ジブロモプロポキシ、３，３，３－トリフルオロプロポキシ、３，３，３－トリフルオロ－２－プロポキシ、３，３，３－トリクロロプロポキシ、３－ブロモ－３，３－ジフルオロプロポキシ、２，２－ジフルオロプロポキシ、３，３－ジクロロ－３－フルオロプロポキシ、２，２，３，３－テトラフルオロプロポキシ、１－ブロモ－３，３，３－トリフルオロプロポキシ、２，２，３，３，３－ペンタフルオロプロポキシ、２，２，２－トリフルオロ－１－トリフルオロメチルエトキシ、ヘプタフルオロプロポキシ、ヘプタフルオロ－２－プロポキシ、１，２，２，２－テトラフルオロ－１－トリフルオロメチルエトキシ、１，１，２，３，３，３－ヘキサフルオロプロポキシ、２－クロロブトキシ、３－クロロブトキシ、４－クロロブトキシ、２－クロロ－１，１－ジメチルエトキシ、４－ブロモブトキシ、３－ブロモ－２－メチルプロポキシ、２－ブロモ－１，１－ジメチルエトキシ、２，２－ジクロロ－１，１－ジメチルエトキシ、２－クロロ－１－クロロメチル－２－メチルエトキシ、４，４，４－トリフルオロブトキシ、３，３，３－トリフルオロ－１－メチルプロポキシ、３，３，３－トリフルオロ－２－メチルプロポキシ、２，３，４－トリクロロブトキシ、２，２，２－トリクロロ－１，１－ジメチルエトキシ、４－クロロ－４，４－ジフルオロブトキシ、４，４－ジクロロ－４－フルオロブトキシ、４－ブロモ－４，４－ジフルオロブトキシ、２，４－ジブロモ－４，４－ジフルオロブトキシ、３，４－ジクロロ－３，４，４－トリフルオロブトキシ、３，３－ジクロロ－４，４，４－トリフルオロブトキシ、４－ブロモ－３，３，４，４－テトラフルオロブトキシ、４－ブロモ－３－クロロ－３，４，４－トリフルオロブトキシ、２，２，３，３，４，４－ヘキサフルオロブトキシ、２，２，３，４，４，４－ヘキサフルオロブトキシ、２，２，２－トリフルオロ－１－メチル－１－トリフルオロメチルエトキシ、３，３，３－トリフルオロ－２－トリフルオロメチルプロポキシ、２，２，３，３，４，４，４－ヘプタフルオロブトキシ、３，３，４，４，４－ペンタフルオロ－２－ブトキシ、２，３，３，３－テトラフルオロ－２－トリフルオロメチルプロポキシ、１，１，２，２，３，３，４，４－オクタフルオロブトキシ、ノナフルオロブトキシ、パーフルオロ－ｔｅｒｔ－ブトキシ、４－クロロ－１，１，２，２，３，３，４，４－オクタフルオロブトキシ、５，５，５－トリフルオロペントキシ、４，４，５，５，５－ペンタフルオロペントキシ、３，３，４，４，５，５，５－ヘプタフルオロペントキシ、３，３，４，４，５，５，５－ヘプタフルオロ－２－ペントキシ、２，２，３，３，４，４，５，５，５－ノナフルオロペントキシ、２，２，３，３，４，４，５，５－オクタフルオロペントキシ、パーフルオロペントキシ、４，４，５，５，５－ペンタフルオロ－２－ブトキシ、２，２－ビス（トリフルロメチル）プロポキシ、２，２，３，３，４，４，５，５，６，６，６－ウンデカフルオロヘキシルオキシ、３，３，４，４，５，５，６，６，６－ノナフルオロヘキシルオキシ、４，４，５，５，６，６，６－ヘプタフルオロヘキシルオキシ、２，２，３，３，４，４，５，５，６，６－デカフルオロヘキシルオキシ、４，４，４－トリフルオロ－３，３－ビス（トリフルオロメチル）ブチルオキシ、パーフルオロヘキシルオキシ等の基を挙げることができる。 In the present invention, “C 1 -C 6 haloalkoxy group” means a (C 1 -C 6 haloalkyl) -O— group in which the haloalkyl moiety has the above-mentioned meaning, unless otherwise specified. Methoxy, trifluoromethoxy, trichloromethoxy, tribromomethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 1-chloroethoxy, 2-chloroethoxy, 1-bromoethoxy, 2-bromoethoxy, 2,2- Difluoroethoxy, 1,2-dichloroethoxy, 2,2-dichloroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 1,1,2,2-tetrafluoroethoxy, pentafluoro Ethoxy, 2-bromo-2-chloroethoxy, 2-chloro- , 1,2,2-tetrafluoroethoxy, 1-chloro-1,2,2,2-tetrafluoroethoxy, 1-chloropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromo Propoxy, 2-bromo-1-methylethoxy, 3-iodopropoxy, 2,3-dichloropropoxy, 2,3-dibromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trifluoro-2 -Propoxy, 3,3,3-trichloropropoxy, 3-bromo-3,3-difluoropropoxy, 2,2-difluoropropoxy, 3,3-dichloro-3-fluoropropoxy, 2,2,3,3-tetra Fluoropropoxy, 1-bromo-3,3,3-trifluoropropoxy, 2,2,3,3,3-pentafluoropropoxy Xy, 2,2,2-trifluoro-1-trifluoromethylethoxy, heptafluoropropoxy, heptafluoro-2-propoxy, 1,2,2,2-tetrafluoro-1-trifluoromethylethoxy, 1,1 , 2,3,3,3-hexafluoropropoxy, 2-chlorobutoxy, 3-chlorobutoxy, 4-chlorobutoxy, 2-chloro-1,1-dimethylethoxy, 4-bromobutoxy, 3-bromo-2- Methylpropoxy, 2-bromo-1,1-dimethylethoxy, 2,2-dichloro-1,1-dimethylethoxy, 2-chloro-1-chloromethyl-2-methylethoxy, 4,4,4-trifluorobutoxy 3,3,3-trifluoro-1-methylpropoxy, 3,3,3-trifluoro-2-methylpropoxy, 2,3,4-tri Chlorobutoxy, 2,2,2-trichloro-1,1-dimethylethoxy, 4-chloro-4,4-difluorobutoxy, 4,4-dichloro-4-fluorobutoxy, 4-bromo-4,4-difluorobutoxy 2,4-dibromo-4,4-difluorobutoxy, 3,4-dichloro-3,4,4-trifluorobutoxy, 3,3-dichloro-4,4,4-trifluorobutoxy, 4-bromo- 3,3,4,4-tetrafluorobutoxy, 4-bromo-3-chloro-3,4,4-trifluorobutoxy, 2,2,3,3,4,4-hexafluorobutoxy, 2,2 3,4,4,4-hexafluorobutoxy, 2,2,2-trifluoro-1-methyl-1-trifluoromethylethoxy, 3,3,3-trifluoro-2-trifluoromethylpropo 2,2,3,3,4,4,4-heptafluorobutoxy, 3,3,4,4,4-pentafluoro-2-butoxy, 2,3,3,3-tetrafluoro-2- Trifluoromethylpropoxy, 1,1,2,2,3,3,4,4-octafluorobutoxy, nonafluorobutoxy, perfluoro-tert-butoxy, 4-chloro-1,1,2,2,3, 3,4,4-octafluorobutoxy, 5,5,5-trifluoropentoxy, 4,4,5,5,5-pentafluoropentoxy, 3,3,4,4,5,5,5- Heptafluoropentoxy, 3,3,4,4,5,5,5-heptafluoro-2-pentoxy, 2,2,3,3,4,4,5,5,5-nonafluoropentoxy, 2 , 2,3,3,4,4,5,5-octafluoropentoxy Perfluoropentoxy, 4,4,5,5,5-pentafluoro-2-butoxy, 2,2-bis (trifluoromethyl) propoxy, 2,2,3,3,4,4,5,5 6,6,6-undecafluorohexyloxy, 3,3,4,4,5,5,6,6,6-nonafluorohexyloxy, 4,4,5,5,6,6,6-hepta Fluorohexyloxy, 2,2,3,3,4,4,5,5,6,6-decafluorohexyloxy, 4,4,4-trifluoro-3,3-bis (trifluoromethyl) butyloxy, Examples include groups such as perfluorohexyloxy.
　本発明において、「Ｃ２～Ｃ６アルケニルオキシ基」とは、特に限定しない限り、アルケニル部分が上記の意味である（Ｃ２～Ｃ６アルケニル）－Ｏ－基を示し、例えば２－プロペニルオキシ、１－メチル－２－プロペニルオキシ、２－メチル－２－プロペニルオキシ、２－ブテニルオキシ、３－ブテニルオキシ、３－メチル－２－ブテニルオキシ、４－メチル－３－ブテニルオキシ、４－ペンテニルオキシ又は５－ヘキセニルオキシ等の基を挙げることができる。 In the present invention, the “C 2 -C 6 alkenyloxy group” refers to a (C 2 -C 6 alkenyl) -O— group in which the alkenyl moiety has the above-mentioned meaning, unless otherwise specified. For example, 2-propenyloxy group , 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-butenyloxy, 3-butenyloxy, 3-methyl-2-butenyloxy, 4-methyl-3-butenyloxy, 4-pentenyloxy or 5- Examples include hexenyloxy and the like.
　本発明において、「Ｃ２～Ｃ６ハロアルケニルオキシ基」とは、特に限定しない限り、ハロアルケニル部分が上記の意味である（Ｃ２～Ｃ６ハロアルケニル）－Ｏ－基を示し、例えば３－クロロ－２－プロペニルオキシ、３，３－ジクロロ－２－プロペニルオキシ、３，３－ジフルオロ－２－プロペニルオキシ、３，３，３－トリフルオロ－１－プロペニルオキシ、２，３，３，３－テトラフルオロ－１－プロペニルオキシ、４，４，４－トリフルオロ－２－ブテニルオキシ、３，４，４－トリフルオロ－３－ブテニルオキシ、５－クロロ－３－ペンテニルオキシ又は６－フルオロ－２－ヘキセニルオキシ等の基を挙げることができる。 In the present invention, the “C 2 -C 6 haloalkenyloxy group” means a (C 2 -C 6 haloalkenyl) -O— group in which the haloalkenyl portion has the above-mentioned meaning, unless otherwise specified. -Chloro-2-propenyloxy, 3,3-dichloro-2-propenyloxy, 3,3-difluoro-2-propenyloxy, 3,3,3-trifluoro-1-propenyloxy, 2,3,3 3-tetrafluoro-1-propenyloxy, 4,4,4-trifluoro-2-butenyloxy, 3,4,4-trifluoro-3-butenyloxy, 5-chloro-3-pentenyloxy or 6-fluoro-2 -Hexenyloxy and the like.
　本発明において、「Ｃ２～Ｃ６アルキニルオキシ基」とは、特に限定しない限り、アルキニル部分が上記の意味である（Ｃ２～Ｃ６アルキニル）－Ｏ－基を示し、例えば２－プロピニルオキシ、１－メチル－２－プロピニルオキシ、１－エチル－２－プロピニルオキシ、２－ブチニルオキシ、３－ブチニルオキシ、１－メチル－２－ブチニルオキシ、２－ペンチニルオキシ、４－ペンチニルオキシ又は４，４－ジメチル－２－ペンチニルオキシ等の基を挙げることができる。 In the present invention, the “C 2 -C 6 alkynyloxy group” means a (C 2 -C 6 alkynyl) -O— group in which the alkynyl moiety has the above-mentioned meaning, unless otherwise specified. For example, 2-propynyloxy , 1-methyl-2-propynyloxy, 1-ethyl-2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-butynyloxy, 2-pentynyloxy, 4-pentynyloxy or 4,4 -Dimethyl-2-pentynyloxy and the like.
　本発明において、「Ｃ２～Ｃ６ハロアルキニルオキシ基」とは、特に限定しない限り、ハロアルキニル部分が上記の意味である（Ｃ２～Ｃ６ハロアルキニル）－Ｏ－基を示し、例えば４，４，４－トリフルオロ－２－ブチニルオキシ、５，５，５－トリフルオロ－３－ペンチニルオキシ又は１－メチル－４，４，４－トリフルオロ－２－ブチニルオキシ等の基を挙げることができる。 In the present invention, “C 2 -C 6 haloalkynyloxy group” means a (C 2 -C 6 haloalkynyl) —O— group in which the haloalkynyl moiety has the above-mentioned meaning, unless otherwise specified. And 4,4,4-trifluoro-2-butynyloxy, 5,5,5-trifluoro-3-pentynyloxy and 1-methyl-4,4,4-trifluoro-2-butynyloxy. it can.
　本発明において、「Ｃ３～Ｃ６シクロアルキルオキシ基」とは、特に限定しない限り、シクロアルキル部分が上記の意味である（Ｃ３～Ｃ６シクロアルキル）－Ｏ－基を示し、例えばシクロプロポキシ、シクロブトキシ、シクロペンチルオキシ又はシクロへキシルオキシ等の基を挙げることができる。 In the present invention, “C 3 -C 6 cycloalkyloxy group” means a (C 3 -C 6 cycloalkyl) -O— group in which the cycloalkyl moiety has the above-mentioned meaning, unless otherwise specified. Examples include groups such as propoxy, cyclobutoxy, cyclopentyloxy or cyclohexyloxy.
　本発明において、「Ｃ３～Ｃ６ハロシクロアルキルオキシ基」とは、特に限定しない限り、ハロシクロアルキル部分が上記の意味である（Ｃ３～Ｃ６ハロシクロアルキル）－Ｏ－基を示し、例えば２，２－ジフルオロシクロプロポキシ、２，２－ジクロロシクロプロポキシ、３，３－ジフルオロシクロブトキシ、３，３－ジクロロシクロブトキシ、３－フルオロシクロペンチルオキシ、３，３－ジフルオロシクロペンチルオキシ、ノナフルオロシクロペンチルオキシ、３，３－ジクロロシクロペンチルオキシ、４，４－ジフルオロシクロヘキシルオキシ又は４，４－ジクロロシクロヘキシルオキシ等の基を挙げることができる。 In the present invention, the “C 3 -C 6 halocycloalkyloxy group” means a (C 3 -C 6 halocycloalkyl) -O— group in which the halocycloalkyl moiety has the above-mentioned meaning, unless otherwise limited. For example, 2,2-difluorocyclopropoxy, 2,2-dichlorocyclopropoxy, 3,3-difluorocyclobutoxy, 3,3-dichlorocyclobutoxy, 3-fluorocyclopentyloxy, 3,3-difluorocyclopentyloxy, nonafluoro Examples include groups such as cyclopentyloxy, 3,3-dichlorocyclopentyloxy, 4,4-difluorocyclohexyloxy, and 4,4-dichlorocyclohexyloxy.
　本発明において、「芳香族複素環オキシ基」とは、特に限定しない限り、芳香族複素環部分が上記の意味である（芳香族複素環）－Ｏ－基を示し、例えばピリジン－２－イルオキシ、ピリジン－３－イルオキシ、ピリジン－４－イルオキシ、ピラジン－２－イルオキシ、ピリダジン－３－イルオキシ、ピリダジン－４－イルオキシ、ピリミジン－２－イルオキシ、ピリミジン－４－イルオキシ、ピリミジン－５－イルオキシ、チアゾール－２－イルオキシ、チアゾール－４－イルオキシ又はチアゾール－５－イルオキシ等の基を挙げることができる。 In the present invention, the term “aromatic heterocyclic oxy group” means a (aromatic heterocyclic) -O— group in which the aromatic heterocyclic moiety has the above-mentioned meaning, unless otherwise specified. For example, pyridin-2-yloxy , Pyridin-3-yloxy, pyridin-4-yloxy, pyrazin-2-yloxy, pyridazin-3-yloxy, pyridazin-4-yloxy, pyrimidin-2-yloxy, pyrimidin-4-yloxy, pyrimidin-5-yloxy, thiazole Groups such as -2-yloxy, thiazol-4-yloxy or thiazol-5-yloxy.
　本発明において、「飽和複素環オキシ基」とは、特に限定しない限り、飽和複素環部分が上記の意味である（飽和複素環）－Ｏ－基を示し、例えばオキセタン－３－イルオキシ、テトラヒドロフラン－２－イルオキシ、テトラヒドロフラン－３－イルオキシ、（テトラヒドロ－２Ｈ－ピラン－２－イル）オキシ、（テトラヒドロ－２Ｈ－ピラン－３－イル）オキシ又は（テトラヒドロ－２Ｈ－ピラン－４－イル）オキシ等の基を挙げることができる。 In the present invention, the “saturated heterocyclic oxy group” refers to a (saturated heterocyclic) -O— group in which the saturated heterocyclic moiety has the above-mentioned meaning, unless otherwise specified. For example, oxetane-3-yloxy, tetrahydrofuran- Such as 2-yloxy, tetrahydrofuran-3-yloxy, (tetrahydro-2H-pyran-2-yl) oxy, (tetrahydro-2H-pyran-3-yl) oxy or (tetrahydro-2H-pyran-4-yl) oxy; Groups.
　本発明において、「Ｃ１～Ｃ６アルキルチオ基」とは、特に限定しない限り、アルキル部分が上記の意味である（Ｃ１～Ｃ６アルキル）－Ｓ－基を示し、例えばメチルチオ、エチルチオ、ｎ－プロピルチオ、イソプロピルチオ、ｎ－ブチルチオ、イソブチルチオ、ｓｅｃ－ブチルチオ又はｔｅｒｔ－ブチルチオ、ペンチルチオ、ヘキシルチオ等の基を挙げることができる。 In the present invention, “C 1 -C 6 alkylthio group” refers to a (C 1 -C 6 alkyl) -S— group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified. For example, methylthio, ethylthio, n -Propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, pentylthio, hexylthio and the like.
　本発明において、「Ｃ１～Ｃ６アルキルスルフィニル基」とは、特に限定しない限り、アルキル部分が上記の意味である（Ｃ１～Ｃ６アルキル）－Ｓ（＝Ｏ）－基を示し、例えばメチルスルフィニル、エチルスルフィニル、ｎ－プロピルスルフィニル、イソプロピルスルフィニル、ｎ－ブチルスルフィニル、イソブチルスルフィニル、ｓｅｃ－ブチルスルフィニル、ｔｅｒｔ－ブチルスルフィニル、ペンチルスルフィニル又はヘキシルスルフィニル等の基を挙げることができる。 In the present invention, “C 1 -C 6 alkylsulfinyl group” refers to a (C 1 -C 6 alkyl) -S (＝ O) — group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified. Examples include groups such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, pentylsulfinyl and hexylsulfinyl.
　本発明において、「Ｃ１～Ｃ６アルキルスルホニル基」とは、特に限定しない限り、アルキル部分が上記の意味である（Ｃ１～Ｃ６アルキル）－Ｓ（＝Ｏ）２－基を示し、例えばメチルスルホニル、エチルスルホニル、ｎ－プロピルスルホニル、イソプロピルスルホニル、ｎ－ブチルスルホニル、イソブチルスルホニル、ｓｅｃ－ブチルスルホニル、ｔｅｒｔ－ブチルスルホニル、ペンチルスルホニル又はヘキシルスルホニル等の基を挙げることができる。 In the present invention, “C 1 -C 6 alkylsulfonyl group” means a (C 1 -C 6 alkyl) -S (＝ O) 2 — group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified. Examples include groups such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, pentylsulfonyl and hexylsulfonyl.
　本発明において、「Ｃ１～Ｃ６ハロアルキルチオ基」とは、特に限定しない限り、ハロアルキル部分が上記の意味である（Ｃ１～Ｃ６ハロアルキル）－Ｓ－基を示し、例えばフルオロメチルチオ、ジフルオロメチルチオ、トリフルオロメチルチオ、トリクロロメチルチオ、２，２，２－トリフルオロエチルチオ、ペンタフルオロエチルチオ、２，２，２－トリクロロエチルチオ、３，３，３－トリフルオロプロピルチオ、１，１，２，３，３，３－ヘキサフルオロプロピルチオ、ヘプタフルオロプロピルチオ、１，１，１，３，３，３－ヘキサフルオロプロパン－２－イルチオ、ヘプタフルオロプロパン－２－イルチオ又は４，４，４－トリフルオロブチルチオ等の基を挙げることができる。 In the present invention, the “C 1 -C 6 haloalkylthio group” refers to a (C 1 -C 6 haloalkyl) -S— group in which the haloalkyl moiety has the above-mentioned meaning, unless otherwise specified, and includes, for example, fluoromethylthio, difluoro Methylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, pentafluoroethylthio, 2,2,2-trichloroethylthio, 3,3,3-trifluoropropylthio, 1,1, 2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1,1,1,3,3,3-hexafluoropropan-2-ylthio, heptafluoropropan-2-ylthio or 4,4 Examples include groups such as 4-trifluorobutylthio.
　本発明において、「Ｃ１～Ｃ６ハロアルキルスルフィニル基」とは、特に限定しない限り、ハロアルキル部分が上記の意味である（Ｃ１～Ｃ６ハロアルキル）－Ｓ（＝Ｏ）－基を示し、例えばジフルオロメチルスルフィニル、トリフルオロメチルスルフィニル、トリクロロメチルスルフィニル、２，２，２－トリフルオロエチルスルフィニル、２，２，２－トリクロロエチルスルフィニル、ペンタフルオロエチルスルフィニル、３，３，３－トリフルオロプロピルスルフィニル、ヘプタフルオロプロピルスルフィニル又はヘプタフルオロ－２－プロピルスルフィニル等の基を挙げることができる。 In the present invention, the “C 1 -C 6 haloalkylsulfinyl group” means a (C 1 -C 6 haloalkyl) -S (＝ O) — group in which the haloalkyl portion has the above-mentioned meaning, unless otherwise specified. Difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, pentafluoroethylsulfinyl, 3,3,3-trifluoropropylsulfinyl, Groups such as heptafluoropropylsulfinyl or heptafluoro-2-propylsulfinyl can be mentioned.
　本発明において、「Ｃ１～Ｃ６ハロアルキルスルホニル基」とは、特に限定しない限り、ハロアルキル部分が上記の意味である（Ｃ１～Ｃ６ハロアルキル）－Ｓ（＝Ｏ）２－基を示し、例えばジフルオロメチルスルホニル、トリフルオロメチルスルホニル、トリクロロメチルスルホニル、２，２，２－トリフルオロエチルスルホニル、ペンタフルオロエチルスルホニル、３，３，３－トリフルオロプロピルスルホニル、ヘプタフルオロプロピルスルホニル、又はヘプタフルオロ－２－プロピルスルホニル等の基を挙げることができる。 In the present invention, the “C 1 -C 6 haloalkylsulfonyl group” means a (C 1 -C 6 haloalkyl) -S (＝ O) 2 — group in which the haloalkyl moiety has the above-mentioned meaning, unless otherwise specified. For example, difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, 3,3,3-trifluoropropylsulfonyl, heptafluoropropylsulfonyl, or heptafluoro- Examples include groups such as 2-propylsulfonyl.
　本発明において、「Ｃ２～Ｃ６アルケニルチオ基」とは、特に限定しない限り、アルケニル部分が上記の意味である（Ｃ２～Ｃ６アルケニル）－Ｓ－基を示し、例えば２－プロペニルチオ、２－ブテニルチオ、３－ブテニルチオ、２－ペンテニルチオ、３－ペンテニルチオ、４－ペンテニルチオ、２－メチル－２－ブテニルチオ、２，４－ペンタジエニルチオ、２－へキセニルチオ、３－ヘキセニルチオ、４－ヘキセニルチオ、５－ヘキセニルチオ又は２，４－ヘキサジエニルチオ等の基を挙げることができる。 In the present invention, the “C 2 -C 6 alkenylthio group” refers to a (C 2 -C 6 alkenyl) -S— group in which the alkenyl moiety has the above-mentioned meaning, unless otherwise specified. For example, 2-propenylthio group , 2-butenylthio, 3-butenylthio, 2-pentenylthio, 3-pentenylthio, 4-pentenylthio, 2-methyl-2-butenylthio, 2,4-pentadienylthio, 2-hexenylthio, 3-hexenylthio , 4-hexenylthio, 5-hexenylthio or 2,4-hexadienylthio.
　本発明において、「Ｃ２～Ｃ６アルケニルスルフィニル基」とは、特に限定しない限り、アルケニル部分が上記の意味である（Ｃ２～Ｃ６アルケニル）－Ｓ（＝Ｏ）－基を示し、例えば２－プロペニルスルフィニル、２－ブテニルスルフィニル、３－ブテニルスルフィニル、２－ペンテニルスルフィニル、３－ペンテニルスルフィニル、４－ペンテニルスルフィニル、２－メチル－２－ブテニルスルフィニル、２，４－ペンタジエニルスルフィニル、２－へキセニルスルフィニル、３－ヘキセニルスルフィニル、４－ヘキセニルスルフィニル、５－ヘキセニルスルフィニル又は２，４－ヘキサジエニルスルフィニル等の基を挙げることができる。 In the present invention, the “C 2 -C 6 alkenylsulfinyl group” means a (C 2 -C 6 alkenyl) -S (＝ O) — group in which the alkenyl moiety has the above-mentioned meaning, unless otherwise specified. 2-propenylsulfinyl, 2-butenylsulfinyl, 3-butenylsulfinyl, 2-pentenylsulfinyl, 3-pentenylsulfinyl, 4-pentenylsulfinyl, 2-methyl-2-butenylsulfinyl, 2,4-pentadienylsulfinyl , 2-hexenylsulfinyl, 3-hexenylsulfinyl, 4-hexenylsulfinyl, 5-hexenylsulfinyl or 2,4-hexadienylsulfinyl.
　本発明において、「Ｃ２～Ｃ６アルケニルスルホニル基」とは、特に限定しない限り、アルケニル部分が上記の意味である（Ｃ２～Ｃ６アルケニル）－Ｓ（＝Ｏ）２－基を示し、例えば２－プロペニルスルホニル、２－ブテニルスルホニル、３－ブテニルスルホニル、２－ペンテニルスルホニル、３－ペンテニルスルホニル、４－ペンテニルスルホニル、２－メチル－２－ブテニルスルホニル、２，４－ペンタジエニルスルホニル、２－へキセニルスルホニル、３－ヘキセニルスルホニル、４－ヘキセニルスルホニル、５－ヘキセニルスルホニル又は２，４－ヘキサジエニルスルホニル等の基を挙げることができる。 In the present invention, the “C 2 -C 6 alkenylsulfonyl group” refers to a (C 2 -C 6 alkenyl) -S (＝ O) 2 — group in which the alkenyl moiety has the above-mentioned meaning, unless otherwise specified. For example, 2-propenylsulfonyl, 2-butenylsulfonyl, 3-butenylsulfonyl, 2-pentenylsulfonyl, 3-pentenylsulfonyl, 4-pentenylsulfonyl, 2-methyl-2-butenylsulfonyl, 2,4-pentadienyl Examples include groups such as sulfonyl, 2-hexenylsulfonyl, 3-hexenylsulfonyl, 4-hexenylsulfonyl, 5-hexenylsulfonyl, and 2,4-hexadienylsulfonyl.
　本発明において、「Ｃ２～Ｃ６ハロアルケニルチオ基」とは、特に限定しない限り、アルケニル部分が上記の意味である（Ｃ２～Ｃ６ハロアルケニル）－Ｓ－基を示し、例えば３－クロロ－２－プロペニルチオ、３，３－ジクロロ－２－プロペニルチオ、３，３－ジフルオロ－２－プロペニルチオ、３，３，３－トリフルオロ－１－プロペニルチオ、２，３，３，３－テトラフルオロ－１－プロペニルチオ、４，４，４－トリフルオロ－２－ブテニルチオ、３，４，４－トリフルオロ－３－ブテニルチオ、５－クロロ－３－ペンテニルチオ又は６－フルオロ－２－ヘキセニルチオ等の基を挙げることができる。 In the present invention, the “C 2 -C 6 haloalkenylthio group” means a (C 2 -C 6 haloalkenyl) -S— group in which the alkenyl moiety has the above-mentioned meaning, unless otherwise specified. Chloro-2-propenylthio, 3,3-dichloro-2-propenylthio, 3,3-difluoro-2-propenylthio, 3,3,3-trifluoro-1-propenylthio, 2,3,3,3 -Tetrafluoro-1-propenylthio, 4,4,4-trifluoro-2-butenylthio, 3,4,4-trifluoro-3-butenylthio, 5-chloro-3-pentenylthio or 6-fluoro-2- Groups such as hexenylthio can be mentioned.
　本発明において、「Ｃ２～Ｃ６ハロアルケニルスルフィニル基」とは、特に限定しない限り、アルケニル部分が上記の意味である（Ｃ２～Ｃ６ハロアルケニル）－Ｓ（＝Ｏ）－基を示し、例えば３－クロロ－２－プロペニルスルフィニル、３，３－ジクロロ－２－プロペニルスルフィニル、３，３－ジフルオロ－２－プロペニルスルフィニル、３，３，３－トリフルオロ－１－プロペニルスルフィニル、２，３，３，３－テトラフルオロ－１－プロペニルスルフィニル、４，４，４－トリフルオロ－２－ブテニルスルフィニル、３，４，４－トリフルオロ－３－ブテニルスルフィニル、５－クロロ－３－ペンテニルスルフィニル又は６－フルオロ－２－ヘキセニルスルフィニル等の基を挙げることができる。 In the present invention, the “C 2 -C 6 haloalkenylsulfinyl group” refers to a (C 2 -C 6 haloalkenyl) -S (＝ O) — group in which the alkenyl moiety has the above-mentioned meaning, unless otherwise specified. For example, 3-chloro-2-propenylsulfinyl, 3,3-dichloro-2-propenylsulfinyl, 3,3-difluoro-2-propenylsulfinyl, 3,3,3-trifluoro-1-propenylsulfinyl, 2,3 , 3,3-tetrafluoro-1-propenylsulfinyl, 4,4,4-trifluoro-2-butenylsulfinyl, 3,4,4-trifluoro-3-butenylsulfinyl, 5-chloro-3-pentenyl Examples include groups such as sulfinyl and 6-fluoro-2-hexenylsulfinyl.
　本発明において、「Ｃ２～Ｃ６ハロアルケニルスルホニル基」とは、特に限定しない限り、アルケニル部分が上記の意味である（Ｃ２～Ｃ６ハロアルケニル）－Ｓ（＝Ｏ）２－基を示し、例えば３－クロロ－２－プロペニルスルホニル、３，３－ジクロロ－２－プロペニルスルホニル、３，３－ジフルオロ－２－プロペニルスルホニル、３，３，３－トリフルオロ－１－プロペニルスルホニル、２，３，３，３－テトラフルオロ－１－プロペニルスルホニル、４，４，４－トリフルオロ－２－ブテニルスルホニル、３，４，４－トリフルオロ－３－ブテニルスルホニル、５－クロロ－３－ペンテニルスルホニル又は６－フルオロ－２－ヘキセニルスルホニル等の基を挙げることができる。 In the present invention, “C 2 -C 6 haloalkenylsulfonyl group” means a (C 2 -C 6 haloalkenyl) -S (＝ O) 2 — group in which the alkenyl portion has the above-mentioned meaning, unless otherwise specified. For example, 3-chloro-2-propenylsulfonyl, 3,3-dichloro-2-propenylsulfonyl, 3,3-difluoro-2-propenylsulfonyl, 3,3,3-trifluoro-1-propenylsulfonyl, 2, 3,3,3-tetrafluoro-1-propenylsulfonyl, 4,4,4-trifluoro-2-butenylsulfonyl, 3,4,4-trifluoro-3-butenylsulfonyl, 5-chloro-3- Examples include groups such as pentenylsulfonyl and 6-fluoro-2-hexenylsulfonyl.
　本発明において、「Ｃ２～Ｃ６アルキニルチオ基」とは、特に限定しない限り、アルキニル部分が上記の意味である（Ｃ２～Ｃ６アルキニル）－Ｓ－基を示し、例えばプロパルギルチオ、１－ブチン－３－イルチオ、３－メチル－１－ブチン－３－イルチオ、２－ブチニルチオ、３－ブチニルチオ、２－ペンチニルチオ、３－ペンチニルチオ、４－ペンチニルチオ又は５－ヘキシニルチオ等の基を挙げることができる。 In the present invention, “C 2 -C 6 alkynylthio group” means a (C 2 -C 6 alkynyl) -S— group in which the alkynyl moiety has the above-mentioned meaning, unless otherwise specified. Groups such as -butyn-3-ylthio, 3-methyl-1-butyn-3-ylthio, 2-butynylthio, 3-butynylthio, 2-pentynylthio, 3-pentynylthio, 4-pentynylthio or 5-hexynylthio. .
　本発明において、「Ｃ２～Ｃ６アルキニルスルフィニル基」とは、特に限定しない限り、アルキニル部分が上記の意味である（Ｃ２～Ｃ６アルキニル）－Ｓ（＝Ｏ）－基を示し、例えばプロパルギルスルフィニル、１－ブチン－３－イルスルフィニル、３－メチル－１－ブチン－３－イルスルフィニル、２－ブチニルスルフィニル、３－ブチニルスルフィニル、２－ペンチニルスルフィニル、３－ペンチニルスルフィニル、４－ペンチニルスルフィニル又は５－ヘキシニルスルフィニル等の基を挙げることができる。 In the present invention, “C 2 -C 6 alkynylsulfinyl group” means a (C 2 -C 6 alkynyl) -S (＝ O) — group in which the alkynyl moiety has the above-mentioned meaning, unless otherwise specified. Propargylsulfinyl, 1-butyn-3-ylsulfinyl, 3-methyl-1-butyn-3-ylsulfinyl, 2-butynylsulfinyl, 3-butynylsulfinyl, 2-pentynylsulfinyl, 3-pentynylsulfinyl, 4 Examples include groups such as -pentynylsulfinyl or 5-hexynylsulfinyl.
　本発明において、「Ｃ２～Ｃ６アルキニルスルホニル基」とは、特に限定しない限り、アルキニル部分が上記の意味である（Ｃ２～Ｃ６アルキニル）－Ｓ（＝Ｏ）２－基を示し、例えばプロパルギルスルホニル、１－ブチン－３－イルスルホニル、３－メチル－１－ブチン－３－イルスルホニル、２－ブチニルスルホニル、３－ブチニルスルホニル、２－ペンチニルスルホニル、３－ペンチニルスルホニル、４－ペンチニルスルホニル又は５－ヘキシニルスルホニル等の基を挙げることができる。 In the present invention, the “C 2 -C 6 alkynylsulfonyl group” refers to a (C 2 -C 6 alkynyl) -S (＝ O) 2 — group in which the alkynyl moiety has the above-mentioned meaning, unless otherwise specified. For example, propargylsulfonyl, 1-butyn-3-ylsulfonyl, 3-methyl-1-butyn-3-ylsulfonyl, 2-butynylsulfonyl, 3-butynylsulfonyl, 2-pentynylsulfonyl, 3-pentynylsulfonyl, Examples include groups such as 4-pentynylsulfonyl and 5-hexynylsulfonyl.
　本発明において、「Ｃ３～Ｃ６シクロアルキルチオ基」とは、特に限定しない限り、シクロアルキル部分が上記の意味である（Ｃ３～Ｃ６シクロアルキル）－Ｓ－基を示し、例えばシクロプロピルチオ、シクロブチルチオ、シクロペンチルチオ又はシクロへキシルチオ等の基を挙げることができる。 In the present invention, “C 3 -C 6 cycloalkylthio group” means a (C 3 -C 6 cycloalkyl) -S— group in which the cycloalkyl moiety has the above-mentioned meaning, unless otherwise specified. Groups such as thio, cyclobutylthio, cyclopentylthio or cyclohexylthio can be mentioned.
　本発明において、「Ｃ３～Ｃ６シクロアルキルスルフィニル基」とは、特に限定しない限り、シクロアルキル部分が上記の意味である（Ｃ３～Ｃ６シクロアルキル）－Ｓ（＝Ｏ）－基を示し、例えばシクロプロピルスルフィニル、シクロブチルスルフィニル、シクロペンチルスルフィニル又はシクロへキシルスルフィニル等の基を挙げることができる。 In the present invention, “C 3 -C 6 cycloalkylsulfinyl group” means a (C 3 -C 6 cycloalkyl) -S (＝ O) — group in which the cycloalkyl moiety has the above-mentioned meaning, unless otherwise specified. And examples thereof include groups such as cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, and cyclohexylsulfinyl.
　本発明において、「Ｃ３～Ｃ６シクロアルキルスルホニル基」とは、特に限定しない限り、シクロアルキル部分が上記の意味である（Ｃ３～Ｃ６シクロアルキル）－Ｓ（＝Ｏ）２－基を示し、例えばシクロプロピルスルホニル、シクロブチルスルホニル、シクロペンチルスルホニル又はシクロへキシルスルホニル等の基を挙げることができる。 In the present invention, “C 3 -C 6 cycloalkylsulfonyl group” means a (C 3 -C 6 cycloalkyl) -S (＝ O) 2 — group in which the cycloalkyl moiety has the above-mentioned meaning, unless otherwise limited. And examples thereof include groups such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl and cyclohexylsulfonyl.
　本発明において、「芳香族複素環チオ基」とは、特に限定しない限り、芳香族複素環部分が上記の意味である（芳香族複素環）－Ｓ－基を示し、例えばピリジン－２－イルチオ、ピリジン－３－イルチオ、ピリジン－４－イルチオ、ピラジン－２－イルチオ、ピリダジン－３－イルチオ、ピリダジン－４－イルチオ、ピリミジン－２－イルチオ、ピリミジン－４－イルチオ、ピリミジン－５－イルチオ、チアゾール－２－イルチオ、チアゾール－４－イルチオ又はチアゾール－５－イルチオ等の基を挙げることができる。 In the present invention, the “aromatic heterocyclic thio group” refers to a (aromatic heterocyclic) -S— group in which the aromatic heterocyclic moiety has the above-mentioned meaning, unless otherwise specified. For example, pyridin-2-ylthio , Pyridin-3-ylthio, pyridin-4-ylthio, pyrazin-2-ylthio, pyridazin-3-ylthio, pyridazin-4-ylthio, pyrimidin-2-ylthio, pyrimidin-4-ylthio, pyrimidin-5-ylthio, thiazole And groups such as -2-ylthio, thiazol-4-ylthio or thiazol-5-ylthio.
　本発明において、「芳香族複素環スルフィニル基」とは、特に限定しない限り、芳香族複素環部分が上記の意味である（芳香族複素環）－Ｓ（＝Ｏ）－基を示し、例えばピリジン－２－イルスルフィニル、ピリジン－３－イルスルフィニル、ピリジン－４－イルスルフィニル、ピラジン－２－イルスルフィニル、ピリダジン－３－イルスルフィニル、ピリダジン－４－イルスルフィニル、ピリミジン－２－イルスルフィニル、ピリミジン－４－イルスルフィニル、ピリミジン－５－イルスルフィニル、チアゾール－２－イルスルフィニル、チアゾール－４－イルスルフィニル又はチアゾール－５－イルスルフィニル等の基を挙げることができる。 In the present invention, the term “aromatic heterocyclic sulfinyl group” means a (aromatic heterocyclic) -S (＝ O) — group in which the aromatic heterocyclic moiety has the above-mentioned meaning, unless otherwise specified. -2-ylsulfinyl, pyridin-3-ylsulfinyl, pyridin-4-ylsulfinyl, pyrazin-2-ylsulfinyl, pyridazin-3-ylsulfinyl, pyridazin-4-ylsulfinyl, pyrimidin-2-ylsulfinyl, pyrimidine- Examples include groups such as 4-ylsulfinyl, pyrimidin-5-ylsulfinyl, thiazol-2-ylsulfinyl, thiazol-4-ylsulfinyl, and thiazol-5-ylsulfinyl.
　本発明において、「芳香族複素環スルホニル基」とは、特に限定しない限り、芳香族複素環部分が上記の意味である（芳香族複素環）－Ｓ（＝Ｏ）２－基を示し、例えばピリジン－２－イルスルホニル、ピリジン－３－イルスルホニル、ピリジン－４－イルスルホニル、ピラジン－２－イルスルホニル、ピリダジン－３－イルスルホニル、ピリダジン－４－イルスルホニル、ピリミジン－２－イルスルホニル、ピリミジン－４－イルスルホニル、ピリミジン－５－イルスルホニル、チアゾール－２－イルスルホニル、チアゾール－４－イルスルホニル又はチアゾール－５－イルスルホニル等の基を挙げることができる。 In the present invention, the “aromatic heterocyclic sulfonyl group” means a (aromatic heterocyclic) -S (＝ O) 2 — group in which the aromatic heterocyclic moiety has the above-mentioned meaning, unless otherwise specified. Pyridin-2-ylsulfonyl, pyridin-3-ylsulfonyl, pyridin-4-ylsulfonyl, pyrazin-2-ylsulfonyl, pyridazin-3-ylsulfonyl, pyridazin-4-ylsulfonyl, pyrimidin-2-ylsulfonyl, pyrimidine Examples of such groups include -4-ylsulfonyl, pyrimidin-5-ylsulfonyl, thiazol-2-ylsulfonyl, thiazol-4-ylsulfonyl, and thiazol-5-ylsulfonyl.
　本発明において、「飽和複素環チオ基」とは、特に限定しない限り、飽和複素環部分が上記の意味である（飽和複素環）－Ｓ－基を示し、例えばオキセタン－３－イルチオ、テトラヒドロフラン－２－イルチオ、テトラヒドロフラン－３－イルチオ、（テトラヒドロ－２Ｈ－ピラン－２－イル）チオ、（テトラヒドロ－２Ｈ－ピラン－３－イル）チオ又は（テトラヒドロ－２Ｈ－ピラン－４－イル）チオ等の基を挙げることができる。 In the present invention, the term “saturated heterocyclic thio group” means a (saturated heterocyclic) -S— group in which the saturated heterocyclic moiety has the above-mentioned meaning, unless otherwise specified. For example, oxetane-3-ylthio, tetrahydrofuran- Such as 2-ylthio, tetrahydrofuran-3-ylthio, (tetrahydro-2H-pyran-2-yl) thio, (tetrahydro-2H-pyran-3-yl) thio or (tetrahydro-2H-pyran-4-yl) thio Groups.
　本発明において、「飽和複素環スルフィニル基」とは、特に限定しない限り、飽和複素環部分が上記の意味である（飽和複素環）－Ｓ（＝Ｏ）－基を示し、例えばオキセタン－３－イルスルフィニル、テトラヒドロフラン－２－イルスルフィニル、テトラヒドロフラン－３－イルスルフィニル、（テトラヒドロ－２Ｈ－ピラン－２－イル）スルフィニル、（テトラヒドロ－２Ｈ－ピラン－３－イル）スルフィニル又は（テトラヒドロ－２Ｈ－ピラン－４－イル）スルフィニル等の基を挙げることができる。 In the present invention, a “saturated heterocyclic sulfinyl group” means a (saturated heterocyclic) -S (（O) — group in which the saturated heterocyclic moiety has the above-mentioned meaning, unless otherwise specified. For example, oxetane-3- Ylsulfinyl, tetrahydrofuran-2-ylsulfinyl, tetrahydrofuran-3-ylsulfinyl, (tetrahydro-2H-pyran-2-yl) sulfinyl, (tetrahydro-2H-pyran-3-yl) sulfinyl or (tetrahydro-2H-pyran- 4-yl) sulfinyl and the like.
　本発明において、「飽和複素環スルホニル基」とは、特に限定しない限り、飽和複素環部分が上記の意味である（飽和複素環）－Ｓ（＝Ｏ）２－基を示し、例えばオキセタン－３－イルスルホニル、テトラヒドロフラン－２－イルスルホニル、テトラヒドロフラン－３－イルスルホニル、（テトラヒドロ－２Ｈ－ピラン－２－イル）スルホニル、（テトラヒドロ－２Ｈ－ピラン－３－イル）スルホニル又は（テトラヒドロ－２Ｈ－ピラン－４－イル）スルホニル等の基を挙げることができる。 In the present invention, the term “saturated heterocyclic sulfonyl group” means a (saturated heterocyclic) -S (ＯO) 2 — group in which the saturated heterocyclic moiety has the above-mentioned meaning, unless otherwise specified. For example, oxetane-3 -Ylsulfonyl, tetrahydrofuran-2-ylsulfonyl, tetrahydrofuran-3-ylsulfonyl, (tetrahydro-2H-pyran-2-yl) sulfonyl, (tetrahydro-2H-pyran-3-yl) sulfonyl or (tetrahydro-2H-pyran -4-yl) sulfonyl and the like.
　本発明において、「Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基」とは、特に限定しない限り、アルコキシ部分及びアルキル部分が上記の意味である（Ｃ１～Ｃ６アルコキシ）－（Ｃ１～Ｃ６アルキル）基を示し、例えばメトキシメチル、エトキシメチル、ｎ－プロポキシメチル、イソプロポキシメチル、ｔｅｒｔ－ブトキシメチル、１－メトキシエチル、１－メトキシ－１－メチルエチル、２－メトキシエチル、１－エトキシエチル、２－エトキシエチル、２－イソプロポキシエチル、３－メトキシプロピル、２－メトキシプロピル、３－エトキシプロピル、４－メトキシブチル又は４－エトキシブチル等の基を挙げることができる。 In the present invention, the “C 1 -C 6 alkoxy C 1 -C 6 alkyl group” means that the alkoxy portion and the alkyl portion have the same meanings as described above, unless otherwise specified (C 1 -C 6 alkoxy)-(C 1 To C 6 alkyl) groups, for example, methoxymethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-methoxy-1-methylethyl, 2-methoxyethyl, And groups such as -ethoxyethyl, 2-ethoxyethyl, 2-isopropoxyethyl, 3-methoxypropyl, 2-methoxypropyl, 3-ethoxypropyl, 4-methoxybutyl or 4-ethoxybutyl.
　本発明において、「Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基」とは、特に限定しない限り、アルキルチオ部分及びアルキル部分が上記の意味である（Ｃ１～Ｃ６アルキルチオ）－（Ｃ１～Ｃ６アルキル）基を示し、例えばメチルチオメチル、２－（メチルチオ）エチル、３－（メチルチオ）プロピル、４－（メチルチオ）ブチル、エチルチオメチル、プロピルチオメチル、ブチルチオメチル又はペンチルチオメチル等の基を挙げることができる。 In the present invention, “C 1 -C 6 alkylthio C 1 -C 6 alkyl group” means, unless otherwise specified, an alkylthio moiety and an alkyl moiety having the above meaning (C 1 -C 6 alkylthio)-(C 1 -C 6 alkyl) group, for example, methylthiomethyl, 2- (methylthio) ethyl, 3- (methylthio) propyl, 4- (methylthio) butyl, ethylthiomethyl, propylthiomethyl, butylthiomethyl or pentylthiomethyl And the group of
　本発明において、「シアノＣ１～Ｃ６アルキル基」とは、特に限定しない限り、アルキル部分が上記の意味である（シアノ）－（Ｃ１～Ｃ６アルキル）基を示し、例えばシアノメチル、１－シアノエチル、２－シアノエチル、３－シアノプロピル、２－シアノプロパン－２－イル、１－シアノブチル、４－シアノブチル、５－シアノペンチル又は６－シアノヘキシル等の基を挙げることができる。 In the present invention, the “cyano C 1 -C 6 alkyl group” means a (cyano)-(C 1 -C 6 alkyl) group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified. Groups such as -cyanoethyl, 2-cyanoethyl, 3-cyanopropyl, 2-cyanopropan-2-yl, 1-cyanobutyl, 4-cyanobutyl, 5-cyanopentyl or 6-cyanohexyl.
　本発明において、「フェニルＣ１～Ｃ６アルキル基」とは、特に限定しない限り、アルキル部分が上記の意味であるフェニル－（Ｃ１～Ｃ６アルキル）基を示し、例えばベンジル、１－フェニルエチル、２－フェニルエチル、３－フェニルプロピル、４－フェニルブチル、５－フェニルペンチル又は６－フェニルヘキシル等の基を挙げることができる。 In the present invention, “phenyl C 1 -C 6 alkyl group” means a phenyl- (C 1 -C 6 alkyl) group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified. Examples include groups such as ethyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl, and 6-phenylhexyl.
　本発明において、「フェニルＣ１～Ｃ６アルコキシ基」とは、特に限定しない限り、アルコキシ部分が上記の意味であるフェニル－（Ｃ１～Ｃ６アルコキシ）基を示し、例えばベンジルオキシ、１－フェニルエチルオキシ、２－フェニルエチルオキシ、３－フェニルプロピルオキシ、４－フェニルブチルオキシ、５－フェニルペンチルオキシ又は６－フェニルヘキシルオキシ等の基を挙げることができる。 In the present invention, “phenyl C 1 -C 6 alkoxy group” means a phenyl- (C 1 -C 6 alkoxy) group in which the alkoxy moiety has the above-mentioned meaning, unless otherwise specified. Examples include groups such as phenylethyloxy, 2-phenylethyloxy, 3-phenylpropyloxy, 4-phenylbutyloxy, 5-phenylpentyloxy, and 6-phenylhexyloxy.
　本発明において、「芳香族複素環Ｃ１～Ｃ６アルキル基」とは、特に限定しない限り、芳香族複素環及びアルキル部分が上記の意味である芳香族複素環－（Ｃ１～Ｃ６アルキル）基を示し、例えばピリジン－２－イルメチル、ピリジン－３－イルメチル、ピリジン－４－イルメチル、ピリジン－２－イルエチル、ピラジン－２－イルメチル、ピリダジン－３－イルメチル、ピリダジン－４－イルメチル、ピリミジン－２－イルメチル、ピリミジン－４－イルメチル、ピリミジン－５－イルメチル、チアゾール－２－イルメチル、チアゾール－４－イルメチル又はチアゾール－５－イルメチル等の基を挙げることができる。 In the present invention, the “aromatic heterocyclic C 1 -C 6 alkyl group” means an aromatic heterocyclic ring- (C 1 -C 6 alkyl) in which the aromatic heterocyclic ring and the alkyl portion have the above-mentioned meanings, unless otherwise specified. ), For example, pyridin-2-ylmethyl, pyridin-3-ylmethyl, pyridin-4-ylmethyl, pyridin-2-ylethyl, pyrazin-2-ylmethyl, pyridazin-3-ylmethyl, pyridazin-4-ylmethyl, pyrimidine- Examples include groups such as 2-ylmethyl, pyrimidin-4-ylmethyl, pyrimidin-5-ylmethyl, thiazol-2-ylmethyl, thiazol-4-ylmethyl or thiazol-5-ylmethyl.
　本発明において、「飽和複素環Ｃ１～Ｃ６アルキル基」とは、特に限定しない限り、飽和複素環及びアルキル部分が上記の意味である飽和複素環－（Ｃ１～Ｃ６アルキル）基を示し、例えばオキセタン－３－イルメチル、テトラヒドロフラン－２－イルメチル、テトラヒドロフラン－３－イルメチル、（テトラヒドロ－２Ｈ－ピラン－２－イル）メチル、（テトラヒドロ－２Ｈ－ピラン－３－イル）メチル又は（テトラヒドロ－２Ｈ－ピラン－４－イル）メチル等の基を挙げることができる。 In the present invention, the “saturated heterocyclic C 1 -C 6 alkyl group” means a saturated heterocyclic ring and a saturated heterocyclic- (C 1 -C 6 alkyl) group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified. For example, oxetan-3-ylmethyl, tetrahydrofuran-2-ylmethyl, tetrahydrofuran-3-ylmethyl, (tetrahydro-2H-pyran-2-yl) methyl, (tetrahydro-2H-pyran-3-yl) methyl or (tetrahydro- 2H-pyran-4-yl) methyl and the like.
　本発明において、「モノ（Ｃ１～Ｃ６アルキル）アミノ基」とは、特に限定しない限り、アルキル部分が上記の意味である（Ｃ１～Ｃ６アルキル）－ＮＨ－基を示し、例えばメチルアミノ、エチルアミノ又はｎ－プロピルアミノ等の基を挙げることができる。 In the present invention, “mono (C 1 -C 6 alkyl) amino group” means a (C 1 -C 6 alkyl) -NH— group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified. Examples include groups such as amino, ethylamino or n-propylamino.
　本発明において、「ジ（Ｃ１～Ｃ６アルキル）アミノ基」とは、特に限定しない限り、アルキル部分が上記の意味である（Ｃ１～Ｃ６アルキル）２－Ｎ－基を示し、２個のアルキル基は互いに異なっていてもよく、例えばジメチルアミノ、メチルエチルアミノ又はメチル－ｎ－プロピルアミノ等の基を挙げることができる。 In the present invention, the term “di (C 1 -C 6 alkyl) amino group” means a (C 1 -C 6 alkyl) 2 —N— group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified. The alkyl groups may be different from each other and include, for example, groups such as dimethylamino, methylethylamino and methyl-n-propylamino.
　本発明において、「Ｃ１～Ｃ６アルキルカルボニルアミノ基」とは、特に限定しない限り、アルキル部分が上記の意味である（Ｃ１～Ｃ６アルキル）－Ｃ（＝Ｏ）－ＮＨ－基を示し、例えばアセチルアミノ、プロピオニルアミノ、ブチリルアミノ又はイソブチリルアミノ等の基を挙げることができる。 In the present invention, “C 1 -C 6 alkylcarbonylamino group” refers to a (C 1 -C 6 alkyl) -C (＝ O) —NH— group in which the alkyl portion has the above-mentioned meaning, unless otherwise limited. And include, for example, groups such as acetylamino, propionylamino, butyrylamino and isobutyrylamino.
　本発明において、「Ｎ－（Ｃ１～Ｃ６アルキルカルボニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基」とは、特に限定しない限り、アミノ基の２つの水素原子がそれぞれ（Ｃ１～Ｃ６アルキル）－Ｃ（＝Ｏ）－基及び（Ｃ１～Ｃ６アルキル）－基で置換された基を示し、例えばＮ－メチルアセチルアミノ、Ｎ－メチルプロピオニルアミノ、Ｎ－メチルブチリルアミノ又はＮ－メチルイソブチリルアミノ等の基を挙げることができる。 In the present invention, "N- (C 1 -C 6 alkylcarbonyl) -N- (C 1 -C 6 alkyl) amino group" means that two hydrogen atoms of an amino group are each (C 1 -C 6 alkyl) -C (＝ O)-and (C 1 -C 6 alkyl) -substituted groups, for example, N-methylacetylamino, N-methylpropionylamino, N-methylbutyryl Examples include groups such as amino or N-methylisobutyrylamino.
　本発明において、「Ｃ１～Ｃ６アルコキシカルボニルアミノ基」とは、特に限定しない限り、アルコキシ部分が上記の意味である（Ｃ１～Ｃ６アルコキシ）－Ｃ（＝Ｏ）－ＮＨ－基を示し、例えばメトキシカルボニルアミノ、エトキシカルボニルアミノ、ｎ－プロポキシカルボニルアミノ又はイソプロポキシカルボニルアミノ等の基を挙げることができる。 In the present invention, “C 1 -C 6 alkoxycarbonylamino group” means a (C 1 -C 6 alkoxy) -C (＝ O) —NH— group in which the alkoxy moiety has the above-mentioned meaning, unless otherwise specified. And include, for example, groups such as methoxycarbonylamino, ethoxycarbonylamino, n-propoxycarbonylamino and isopropoxycarbonylamino.
　本発明において、「Ｎ－（Ｃ１～Ｃ６アルコキシカルボニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基」とは、特に限定しない限り、アミノ基の２つの水素原子がそれぞれ（Ｃ１～Ｃ６アルコキシ）－Ｃ（＝Ｏ）－基及び（Ｃ１～Ｃ６アルキル）－基で置換された基を示し、例えばメトキシカルボニル－（Ｎ－メチル）－アミノ、エトキシカルボニル－（Ｎ－メチル）－アミノ、ｎ－プロポキシカルボニル－（Ｎ－メチル）－アミノ又はイソプロポキシカルボニル－（Ｎ－メチル）－アミノ等の基を挙げることができる。 In the present invention, “N- (C 1 -C 6 alkoxycarbonyl) -N- (C 1 -C 6 alkyl) amino group” means that two hydrogen atoms of an amino group are each (C 1 -C 6 alkoxy) -C (＝ O)-group and a group substituted with (C 1 -C 6 alkyl)-group, for example, methoxycarbonyl- (N-methyl) -amino, ethoxycarbonyl- (N- Examples include groups such as methyl) -amino, n-propoxycarbonyl- (N-methyl) -amino, and isopropoxycarbonyl- (N-methyl) -amino.
　本発明において、「Ｃ１～Ｃ６アルキルスルホニルアミノ基」とは、特に限定しない限り、アルキル部分が上記の意味である（Ｃ１～Ｃ６アルキル）－Ｓ（＝Ｏ）２－ＮＨ－基を示し、例えばメチルスルホニルアミノ、エチルスルホニルアミノ、ｎ－プロピルスルホニルアミノ、イソプロピルスルホニルアミノ又はｔｅｒｔ－ブチルスルホニルアミノ等の基を挙げることができる。 In the present invention, “C 1 -C 6 alkylsulfonylamino group” means a (C 1 -C 6 alkyl) -S (＝ O) 2 —NH— group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified. And examples thereof include groups such as methylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino, isopropylsulfonylamino and tert-butylsulfonylamino.
　本発明において、「Ｎ－（Ｃ１～Ｃ６アルキルスルホニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基」とは、特に限定しない限り、アミノ基の２つの水素原子がそれぞれ（Ｃ１～Ｃ６アルキル）－Ｓ（＝Ｏ）２－基及び（Ｃ１～Ｃ６アルキル）－基で置換された基を示し、例えばＮ－メチルメチルスルホニルアミノ、Ｎ－メチルエチルスルホニルアミノ、Ｎ－メチル－ｎ－プロピルスルホニルアミノ、Ｎ－メチルイソプロピルスルホニルアミノ又はＮ－メチル－ｔｅｒｔ－ブチルスルホニルアミノ等の基を挙げることができる。 In the present invention, “N- (C 1 -C 6 alkylsulfonyl) -N- (C 1 -C 6 alkyl) amino group” means that two hydrogen atoms of the amino group are each (C 1 -C 6 alkyl) -S (＝ O) 2- and (C 1 -C 6 alkyl) -substituted groups, for example, N-methylmethylsulfonylamino, N-methylethylsulfonylamino, N- Examples thereof include groups such as methyl-n-propylsulfonylamino, N-methylisopropylsulfonylamino, and N-methyl-tert-butylsulfonylamino.
　本発明において、「Ｃ１～Ｃ６ハロアルキルスルホニルアミノ基」とは、特に限定しない限り、ハロアルキル部分が上記の意味である（Ｃ１～Ｃ６ハロアルキル）－Ｓ（＝Ｏ）２－ＮＨ－基を示し、例えばフルオロメチルスルホニルアミノ、ジフルオロメチルスルホニルアミノ、トリフルオロメチルスルホニルアミノ、クロロメチルスルホニルアミノ、トリクロロメチルスルホニルアミノ、２，２，２－トリフルオロエチルスルホニルアミノ、２，２－ジフルオロエチルスルホニルアミノ又は３，３，３－トリフルオロプロピルスルホニルアミノ等の基を挙げることができる。 In the present invention, “C 1 -C 6 haloalkylsulfonylamino group” means a (C 1 -C 6 haloalkyl) -S (＝ O) 2 —NH— group in which the haloalkyl portion has the above-mentioned meaning, unless otherwise specified. Represents, for example, fluoromethylsulfonylamino, difluoromethylsulfonylamino, trifluoromethylsulfonylamino, chloromethylsulfonylamino, trichloromethylsulfonylamino, 2,2,2-trifluoroethylsulfonylamino, 2,2-difluoroethylsulfonylamino Or groups such as 3,3,3-trifluoropropylsulfonylamino.
　本発明において、「Ｎ－（Ｃ１～Ｃ６ハロアルキルスルホニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基」とは、特に限定しない限り、アミノ基の２つの水素原子がそれぞれ（Ｃ１～Ｃ６ハロアルキル）－Ｓ（＝Ｏ）２－基及び（Ｃ１～Ｃ６アルキル）－基で置換された基を示し、例えばＮ－メチルフルオロメチルスルホニルアミノ、Ｎ－メチルジフルオロメチルスルホニルアミノ、Ｎ－メチルトリフルオロメチルスルホニルアミノ、Ｎ－メチルクロロメチルスルホニルアミノ、Ｎ－メチルトリクロロメチルスルホニルアミノ、Ｎ－メチル－２，２，２－トリフルオロエチルスルホニルアミノ、Ｎ－メチル－２，２－ジフルオロエチルスルホニルアミノ又はＮ－メチル－３，３，３－トリフルオロプロピルスルホニルアミノ等の基を挙げることができる。 In the present invention, “N- (C 1 -C 6 haloalkylsulfonyl) -N- (C 1 -C 6 alkyl) amino group” means that two hydrogen atoms of the amino group are each (C 1 -C 6 haloalkyl) -S (= O) 2- and a group substituted with a (C 1 -C 6 alkyl)-group, such as N-methylfluoromethylsulfonylamino, N-methyldifluoromethylsulfonylamino, N-methyltrifluoromethylsulfonylamino, N-methylchloromethylsulfonylamino, N-methyltrichloromethylsulfonylamino, N-methyl-2,2,2-trifluoroethylsulfonylamino, N-methyl-2,2-difluoro Groups such as ethylsulfonylamino or N-methyl-3,3,3-trifluoropropylsulfonylamino It can be mentioned.
　本発明において、「モノ（Ｃ１～Ｃ６アルキル）アミノカルボニル基」とは、特に限定しない限り、アルキル部分が上記の意味である（Ｃ１～Ｃ６アルキル）－ＮＨ－Ｃ（＝Ｏ）－基を示し、例えばメチルアミノカルボニル、エチルアミノカルボニル、プロピルアミノカルボニル又はイソプロピルアミノカルボニル等の基を挙げることができる。 In the present invention, the “mono (C 1 -C 6 alkyl) aminocarbonyl group” means that the alkyl portion has the above-mentioned meaning (C 1 -C 6 alkyl) -NH—C (＝ O) unless otherwise specified. And represents a group such as methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl or isopropylaminocarbonyl.
　本発明において、「ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル基」とは、特に限定しない限り、アルキル部分が上記の意味である（Ｃ１～Ｃ６アルキル）２－Ｎ－Ｃ（＝Ｏ）－基を示し、２個のアルキル基は互いに異なっていてもよく、例えばジメチルアミノカルボニル、ジエチルアミノカルボニル又はジイソプロピルアミノカルボニル等の基を挙げることができる。 In the present invention, the term “di (C 1 -C 6 alkyl) aminocarbonyl group” means that the alkyl portion has the above-mentioned meaning (C 1 -C 6 alkyl) 2 —NC (ＣO), unless otherwise specified. )-, And the two alkyl groups may be different from each other, and examples thereof include groups such as dimethylaminocarbonyl, diethylaminocarbonyl and diisopropylaminocarbonyl.
　本発明において、「モノ（Ｃ１～Ｃ６ハロアルキル）アミノカルボニル基」とは、特に限定しない限り、ハロアルキル部分が上記の意味である（Ｃ１～Ｃ６ハロアルキル）－ＮＨ－Ｃ（＝Ｏ）－基を示し、例えば２－フルオロエチルアミノカルボニル、２，２，２－トリフルオロエチルアミノカルボニル、２，２，２－トリクロロエチルアミノカルボニル又は１，１，１，３，３，３－ヘキサフルオロ－２－プロピルアミノカルボニル等の基を挙げることができる。 In the present invention, the term “mono (C 1 -C 6 haloalkyl) aminocarbonyl group” means that the haloalkyl moiety has the above-mentioned meaning, unless otherwise specified. (C 1 -C 6 haloalkyl) -NH—C (＝ O) And represents, for example, 2-fluoroethylaminocarbonyl, 2,2,2-trifluoroethylaminocarbonyl, 2,2,2-trichloroethylaminocarbonyl or 1,1,1,3,3,3-hexafluoro And groups such as -2-propylaminocarbonyl.
　本発明において、「Ｒ７によって任意に置換されたＣ１～Ｃ６アルキル基」、「Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキル基」等の表記は、炭素原子に結合した水素原子が任意のＲ７又はＲ１３によって、置換されたアルキル基を表し、置換されるＲ７又はＲ１３の数は各々の指定の炭素原子数の範囲で任意に選択される。アルキル基上の置換基Ｒ７又はＲ１３が２個以上存在するとき、それぞれのＲ７又はＲ１３は互いに同一でも、または互いに相異なっていてもよい。 In the present invention, notations such as “C 1 -C 6 alkyl group optionally substituted by R 7 ” and “C 1 -C 6 alkyl group optionally substituted by R 13 ” refer to hydrogen bonded to a carbon atom. by atomic any R 7 or R 13, represents a substituted alkyl group, the number of R 7 or R 13 are substituted are selected arbitrarily in the range of number of carbon atoms of each of the specified. When there are two or more substituents R 7 or R 13 on the alkyl group, each R 7 or R 13 may be the same or different from each other.
　本発明において、「Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキル基」等の表記は、炭素原子に結合した水素原子が任意のＲ１３によって、置換されたハロアルキル基を表し、置換されるＲ１３の数は各々の指定の炭素原子数の範囲で任意に選択される。
ハロアルキル基上の置換基Ｒ１３が２個以上存在するとき、それぞれのＲ１３は互いに同一でも、または互いに相異なっていてもよい。 In the present invention, the notation such as "C 1 ~ C 6 haloalkyl group optionally substituted by R 13" by any R 13 is a hydrogen atom bonded to a carbon atom, a substituted haloalkyl group, substituted The number of R 13 is arbitrarily selected within the range of the specified number of carbon atoms.
When there are two or more substituents R 13 on the haloalkyl group, each R 13 may be the same or different from each other.
　本発明において、「Ｒ８によって任意に置換されたＣ３～Ｃ６シクロアルキル基」等の表記は、炭素原子に結合した水素原子が任意のＲ８によって、置換されたシクロアルキル基を表し、置換されるＲ８の数は各々の指定の炭素原子数の範囲で任意に選択される。シクロアルキル基上の置換基Ｒ８が２個以上存在するとき、それぞれのＲ８は互いに同一でも、または互いに相異なっていてもよい。 In the present invention, the notation such as "C 3 ~ C 6 cycloalkyl group optionally substituted by R 8 'is, by any R 8 is a hydrogen atom bonded to a carbon atom, a substituted cycloalkyl group, The number of substituted R 8 is arbitrarily selected within the range of each specified number of carbon atoms. When there are two or more substituents R 8 on the cycloalkyl group, each R 8 may be the same or different from each other.
　本発明において、「Ｒ１３によって任意に置換されたＣ２～Ｃ６アルケニル基」等の表記は、炭素原子に結合した水素原子が任意のＲ１３によって、置換されたアルケニル基を表し、置換されるＲ１３の数は各々の指定の炭素原子数の範囲で任意に選択される。アルケニル基上の置換基Ｒ１３が２個以上存在するとき、それぞれのＲ１３は互いに同一でも、または互いに相異なっていてもよい。 In the present invention, the notation such as "C 2 ~ C 6 alkenyl group optionally substituted by R 13" by any R 13 is hydrogen atoms bonded to carbon atoms, a substituted alkenyl group, substituted The number of R 13 is arbitrarily selected within the range of the specified number of carbon atoms. When there are two or more substituents R 13 on the alkenyl group, each R 13 may be the same as or different from each other.
　本発明において、「Ｒ１３によって任意に置換されたＣ２～Ｃ６アルキニル基」等の表記は、炭素原子に結合した水素原子が任意のＲ１３によって、任意に置換されたアルキニル基を表し、置換されるＲ１３の数は各々の指定の炭素原子数の範囲で任意に選択される。アルキニル基上の置換基Ｒ１３が２個以上存在するとき、それぞれのＲ１３は互いに同一でも、または互いに相異なっていてもよい。 In the present invention, the notation such as "C 2 ~ C 6 alkynyl group optionally substituted by R 13" by any R 13 is a hydrogen atom bonded to a carbon atom, a substituted alkynyl group optionally The number of R 13 to be substituted is arbitrarily selected within the range of each specified number of carbon atoms. When there are two or more substituents R 13 on the alkynyl group, each R 13 may be the same as or different from each other.
　本発明において、「Ｒ７によって任意に置換されたＣ１～Ｃ６アルコキシ基」、「Ｒ１３によって任意に置換されたＣ１～Ｃ６アルコキシ基」等の表記は、炭素原子に結合した水素原子が任意のＲ７又はＲ１３によって、置換されたアルコキシ基を表し、置換されるＲ７又はＲ１３の数は各々の指定の炭素原子数の範囲で任意に選択される。アルコキシ基上の置換基Ｒ７又はＲ１３が２個以上存在するとき、それぞれのＲ７又はＲ１３は互いに同一でも、または互いに相異なっていてもよい。 In the present invention, notations such as “C 1 -C 6 alkoxy group optionally substituted by R 7 ” and “C 1 -C 6 alkoxy group optionally substituted by R 13 ” refer to hydrogen bonded to a carbon atom. by atomic any R 7 or R 13, represents a substituted alkoxy group, the number of R 7 or R 13 are substituted are selected arbitrarily in the range of number of carbon atoms of each of the specified. When two or more substituents R 7 or R 13 on the alkoxy group are present, each R 7 or R 13 may be the same or different from each other.
　本発明において、「Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルコキシ基」等の表記は、炭素原子に結合した水素原子が任意のＲ１３によって、置換されたハロアルコキシ基を表し、置換されるＲ１３の数は各々の指定の炭素原子数の範囲で任意に選択される。ハロアルコキシ基上の置換基Ｒ１３が２個以上存在するとき、それぞれのＲ１３は互いに同一でも、または互いに相異なっていてもよい。 In the present invention, the notation such as "C 1 ~ C 6 haloalkoxy group optionally substituted by R 13" are hydrogen atoms bonded to carbon atoms by any R 13, represents a substituted haloalkoxy group, The number of R 13 to be substituted is arbitrarily selected within the range of each specified number of carbon atoms. When there are two or more substituents R 13 on the haloalkoxy group, each R 13 may be the same or different from each other.
　本発明において、「Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルチオ基」等の表記は、炭素原子に結合した水素原子が任意のＲ１３によって、置換されたアルキルチオ基を表し、置換されるＲ１３の数は各々の指定の炭素原子数の範囲で任意に選択される。
アルキルチオ基上の置換基Ｒ１３が２個以上存在するとき、それぞれのＲ１３は互いに同一でも、または互いに相異なっていてもよい。 In the present invention, the notation such as "C 1 ~ C 6 alkylthio group optionally substituted by R 13" by any R 13 is a hydrogen atom bonded to a carbon atom, a substituted alkylthio group, substituted The number of R 13 is arbitrarily selected within the range of the specified number of carbon atoms.
When there are two or more substituents R 13 on the alkylthio group, each R 13 may be the same or different from each other.
　本発明において、「Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルスルフィニル基」等の表記は、炭素原子に結合した水素原子が任意のＲ１３によって、置換されたアルキルスルフィニル基を表し、置換されるＲ１３の数は各々の指定の炭素原子数の範囲で任意に選択される。アルキルスルフィニル基上の置換基Ｒ１３が２個以上存在するとき、それぞれのＲ１３は互いに同一でも、または互いに相異なっていてもよい。 In the present invention, the notation such as "optionally substituted C 1 ~ C 6 alkylsulfinyl group by R 13" by any R 13 is a hydrogen atom bonded to a carbon atom, a substituted alkylsulfinyl group, The number of R 13 to be substituted is arbitrarily selected within the range of each specified number of carbon atoms. When two or more substituents R 13 on the alkylsulfinyl group are present, each R 13 may be the same as or different from each other.
　本発明において、「Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルスルホニル基」等の表記は、炭素原子に結合した水素原子が任意のＲ１３によって、置換されたアルキルスルホニル基を表し、置換されるＲ１３の数は各々の指定の炭素原子数の範囲で任意に選択される。アルキルスルホニル基上の置換基Ｒ１３が２個以上存在するとき、それぞれのＲ１３は互いに同一でも、または互いに相異なっていてもよい。 In the present invention, the notation such as "C 1 ~ C 6 alkylsulfonyl group optionally substituted by R 13" by any R 13 is a hydrogen atom bonded to a carbon atom, a substituted alkylsulfonyl group, The number of R 13 to be substituted is arbitrarily selected within the range of each specified number of carbon atoms. When there are two or more substituents R 13 on the alkylsulfonyl group, each R 13 may be the same as or different from each other.
　本発明において、「Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルチオ基」等の表記は、炭素原子に結合した水素原子が任意のＲ１３によって、置換されたハロアルキルチオ基を表し、置換されるＲ１３の数は各々の指定の炭素原子数の範囲で任意に選択される。ハロアルキルチオ基上の置換基Ｒ１３が２個以上存在するとき、それぞれのＲ１３は互いに同一でも、または互いに相異なっていてもよい。 In the present invention, the notation such as "C 1 ~ C 6 haloalkylthio group optionally substituted by R 13" by any R 13 is a hydrogen atom attached to the carbon atom, a substituted haloalkylthio group, The number of R 13 to be substituted is arbitrarily selected within the range of each specified number of carbon atoms. When there are two or more substituents R 13 on the haloalkylthio group, each R 13 may be the same as or different from each other.
　本発明において、「Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルスルフィニル基」等の表記は、炭素原子に結合した水素原子が任意のＲ１３によって、置換されたハロアルキルスルフィニル基を表し、置換されるＲ１３の数は各々の指定の炭素原子数の範囲で任意に選択される。ハロアルキルスルフィニル基上の置換基Ｒ１３が２個以上存在するとき、それぞれのＲ１３は互いに同一でも、または互いに相異なっていてもよい。 In the present invention, the notation such as "C 1 ~ C 6 haloalkylsulfinyl group optionally substituted by R 13" by any R 13 is a hydrogen atom bonded to a carbon atom, a substituted haloalkylsulfinyl group, The number of R 13 to be substituted is arbitrarily selected within the range of each specified number of carbon atoms. When there are two or more substituents R 13 on the haloalkylsulfinyl group, each R 13 may be the same as or different from each other.
　本発明において、「Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルスルホニル基」等の表記は、炭素原子に結合した水素原子が任意のＲ１３によって、置換されたハロアルキルスルホニル基を表し、置換されるＲ１３の数は各々の指定の炭素原子数の範囲で任意に選択される。ハロアルキルスルホニル基上の置換基Ｒ１３が２個以上存在するとき、それぞれのＲ１３は互いに同一でも、または互いに相異なっていてもよい。 In the present invention, the notation such as "optionally substituted C 1 ~ C 6 haloalkylsulfonyl group by R 13" by any R 13 is a hydrogen atom bonded to a carbon atom, a substituted haloalkylsulfonyl group, The number of R 13 to be substituted is arbitrarily selected within the range of each specified number of carbon atoms. When there are two or more substituents R 13 on the haloalkylsulfonyl group, each R 13 may be the same as or different from each other.
　本発明において、［Ｒ１及びＲ２は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく］、［Ｒ９及びＲ１０は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく］、［Ｒ１１及びＲ１２は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく］又は［Ｒ１２及びＲ１４は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく］等の表記の、当該アルキレン結合及び当該アルキレン結合と隣り合う原子によって形成されるヘテロ環の具体例として、例えばアジリジン、アゼチジン、ピロリジン、オキサゾリジン、オキサゾリン、イソキサゾリン、チアゾリジン、イミダゾリジン、ピペリジン、モルホリン、チオモルホリン、チオモルホリン－１－オキシド、チオモルホリン－１，１－ジオキシド、ピペラジン、ホモピペリジン又はヘプタメチレンイミン等の基を挙げることができる。 In the present invention, [R 1 and R 2 may be bonded to each other to form a C 2 to C 6 alkylene bond, wherein the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom. Well], [R 9 and R 10 may combine with each other to form a C 2 -C 6 alkylene bond, wherein the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom. ], [R 11 and R 12 may combine with each other to form a C 2 -C 6 alkylene bond, in which case the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom] Or [R 12 and R 14 may be mutually bonded to form a C 2 -C 6 alkylene bond, in which case the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom], and the like. Notation of Specific examples of the alkylene bond and the heterocyclic ring formed by the atom adjacent to the alkylene bond include, for example, aziridine, azetidine, pyrrolidine, oxazolidine, oxazoline, isoxazoline, thiazolidine, imidazolidine, piperidine, morpholine, thiomorpholine, thiomorpholine- Examples include groups such as 1-oxide, thiomorpholine-1,1-dioxide, piperazine, homopiperidine or heptamethyleneimine.
　本発明において、［Ｒ１４及びＲ１５は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく］等の表記の、当該アルキレン結合及び当該アルキレン結合と隣り合う原子によって形成されるヘテロ環の具体例として、例えば４，５－ジヒドロイソキサゾール等の基を挙げることができる。 In the present invention, [R 14 and R 15 may be mutually bonded to form a C 2 -C 6 alkylene bond, wherein the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom. Examples of the heterocyclic ring formed by the alkylene bond and the atom adjacent to the alkylene bond, such as 4,5-dihydroisoxazole, may be mentioned.
　本発明において、［Ｃ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく］等の表記は、アルキレン結合を構成する炭素原子に結合した水素原子がハロゲン原子又はＣ１～Ｃ６アルキル基によって置換されたＣ２～Ｃ６アルキレン結合を表し、置換されるハロゲン原子又はＣ１～Ｃ６アルキル基の数は、モノ置換の場合には置換基としてハロゲン原子又はＣ１～Ｃ６アルキル基のいずれか一つが置換していることを表し、ポリ置換の場合は置換基として２個以上のハロゲン原子又はＣ１～Ｃ６アルキル基のいずれかが置換していることを表す。また、Ｃ２～Ｃ６アルキレン結合上にポリ置換の場合（すなわち２個以上置換基が存在するとき）、それぞれの置換基は互いに同一でも、または互いに相異なっていてもよい。 In the present invention, the notation such as [the C 2 -C 6 alkylene bond may be mono- or poly-substituted by a halogen atom or a C 1 -C 6 alkyl group] represents hydrogen bonded to a carbon atom constituting the alkylene bond. atom represents a C 2 ~ C 6 alkylene linkage substituted by halogen atom or C 1 ~ C 6 alkyl group, the number of halogen atoms or C 1 ~ C 6 alkyl group is substituted, the substituent in the case of the mono-substituted Represents that any one of a halogen atom or a C 1 -C 6 alkyl group is substituted, and in the case of poly substitution, any one of two or more halogen atoms or a C 1 -C 6 alkyl group is substituted. Represents substitution. Also, when poly-substituted on the C 2 -C 6 alkylene bond (ie, when two or more substituents are present), each substituent may be the same as or different from each other.
　本発明において、農業上許容される塩及び塩とは、一般式［Ｉ］で表される本発明の化合物において、水酸基、カルボキシル基又はアミノ基等がその構造中に存在する場合に、これらと金属若しくは有機塩基との塩又は鉱酸若しくは有機酸との塩であり、金属としてはナトリウム若しくはカリウム等のアルカリ金属或いはマグネシウム若しくはカルシウム等のアルカリ土類金属を挙げることができ、有機塩基としてはトリエチルアミン若しくはジイソプロピルアミン等を挙げることができ、鉱酸としては塩酸、臭化水素酸若しくは硫酸等を挙げることができ、又、有機酸としては、ギ酸、酢酸、メタンスルホン酸、４－トルエンスルホン酸若しくはトリフルオロメタンスルホン酸等を挙げることができる。 In the present invention, agriculturally acceptable salts and salts refer to the compounds of the present invention represented by the general formula [I] when a hydroxyl group, a carboxyl group, an amino group or the like is present in the structure. A salt with a metal or an organic base or a salt with a mineral acid or an organic acid; examples of the metal include an alkali metal such as sodium or potassium or an alkaline earth metal such as magnesium or calcium; and an organic base such as triethylamine Or mineral acids such as hydrochloric acid, hydrobromic acid or sulfuric acid, and organic acids such as formic acid, acetic acid, methanesulfonic acid, 4-toluenesulfonic acid or Trifluoromethanesulfonic acid and the like can be mentioned.
　次に、一般式［Ｉ］で表される本発明の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体に包含される化合物の代表的な化合物例を表１から表２５に、一般式［ＩＩ］で表される本発明の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸誘導体に包含される化合物の代表的な化合物例を表２６から表５５に、一般式［ＩＩＩ］で表される本発明の１－フェニル－１Ｈ－１，２，４－トリアゾール誘導体に包含される化合物の代表的な化合物例を表５６から表５８に示す。しかしながら、本発明の誘導体に包含される化合物は、これらに限定されるものではない。又、表中の化合物番号は以後の記載において参照される。 Next, Table 1 shows typical examples of compounds included in the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative of the present invention represented by the general formula [I]. To Table 25 show typical examples of compounds included in the 3- (1H-1,2,4-triazol-1-yl) benzoic acid derivative of the present invention represented by the general formula [II]. 26 to Table 55, Table 56 to Table 58 show typical compound examples of the compounds included in the 1-phenyl-1H-1,2,4-triazole derivative of the present invention represented by the general formula [III]. Show. However, the compounds included in the derivative of the present invention are not limited to these. The compound numbers in the table will be referred to in the following description.
　尚、本発明の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体、３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸誘導体又は１－フェニル－１Ｈ－１，２，４－トリアゾール誘導体に包含される化合物には、置換基の種類によってはＥ－体及びＺ－体の幾何異性体が存在する場合があるが、本発明はこれらＥ－体、Ｚ－体又はＥ－体及びＺ－体を任意の割合で含む混合物を包含する。又、本発明に包含される化合物は、１個又は２個以上の不斉炭素原子及び不斉硫黄原子の存在に起因する光学異性体が存在する場合があるが、本発明は全ての光学活性体、ラセミ体又はジアステレオマーを包含する。 The 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative, 3- (1H-1,2,4-triazol-1-yl) benzoic acid derivative or 1- (1H-1,2,4-triazol-1-yl) benzoic acid derivative of the present invention The compound included in the phenyl-1H-1,2,4-triazole derivative may have an E-form or a Z-form geometric isomer depending on the type of the substituent. -Forms, Z-forms or mixtures containing E-forms and Z-forms in any proportion. The compounds included in the present invention may have optical isomers due to the presence of one or more asymmetric carbon atoms and asymmetric sulfur atoms, but the present invention relates to all optically active compounds. , Racemates or diastereomers.
　本明細書における表中の次の表記は、例えば下記の通りそれぞれ該当する基を表す。
　　Ｍｅ　　　：メチル、
　　Ｅｔ　　　：エチル、
　　ｎ－Ｐｒ　：ノルマルプロピル、
　　ｉ－Ｐｒ　：イソプロピル、
　　ｃ－Ｐｒ　：シクロプロピル、
　　ｎ－Ｂｕ　：ノルマルブチル、
　　ｓ－Ｂｕ　：セカンダリーブチル、
　　ｉ－Ｂｕ　：イソブチル、
　　ｔ－Ｂｕ　：ターシャリーブチル、
　　ｃ－Ｂｕ　：シクロブチル、
　　ｎ－Ｐｅｎ：ノルマルペンチル、
　　ｃ－Ｐｅｎ：シクロペンチル、
　　ｎ－Ｈｅｘ：ノルマルヘキシル、
　　ｃ－Ｈｅｘ：シクロヘキシル、
　　ｃ－Ｐｒ（２，２－Ｆ２）：２，２－ジフルオロシクロプロピル
　　Ｐｈ　　　：フェニル、
　　３－Ｐｙ　：３－ピリジル
　　Ｐｈ（４－ＣＦ３）：４－トリフルオロメチルフェニル、
　　Ｐｈ（３－ＯＭｅ，４－ＯＨ）：４－ヒドロキシ－３－メトキシフェニル、 The following notation in the table in this specification represents a corresponding group, for example, as follows.
Me: methyl,
Et: ethyl,
n-Pr: normal propyl,
i-Pr: isopropyl,
c-Pr: cyclopropyl,
n-Bu: normal butyl,
s-Bu: secondary butyl,
i-Bu: isobutyl,
t-Bu: tertiary butyl,
c-Bu: cyclobutyl,
n-Pen: normal pentyl,
c-Pen: cyclopentyl,
n-Hex: normal hexyl,
c-Hex: cyclohexyl,
c-Pr (2,2-F 2 ): 2,2-difluorocyclopropyl Ph: phenyl,
3-Py: 3-pyridyl Ph (4-CF 3 ): 4-trifluoromethylphenyl,
Ph (3-OMe, 4-OH): 4-hydroxy-3-methoxyphenyl,
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
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
Figure JPOXMLDOC01-appb-T000051
Figure JPOXMLDOC01-appb-T000051
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
Figure JPOXMLDOC01-appb-T000059
Figure JPOXMLDOC01-appb-T000059
Figure JPOXMLDOC01-appb-T000060
Figure JPOXMLDOC01-appb-T000060
Figure JPOXMLDOC01-appb-T000061
Figure JPOXMLDOC01-appb-T000061
Figure JPOXMLDOC01-appb-T000062
Figure JPOXMLDOC01-appb-T000062
Figure JPOXMLDOC01-appb-T000063
Figure JPOXMLDOC01-appb-T000063
Figure JPOXMLDOC01-appb-T000064
Figure JPOXMLDOC01-appb-T000064
Figure JPOXMLDOC01-appb-T000065
Figure JPOXMLDOC01-appb-T000065
Figure JPOXMLDOC01-appb-T000066
Figure JPOXMLDOC01-appb-T000066
Figure JPOXMLDOC01-appb-T000067
Figure JPOXMLDOC01-appb-T000067
Figure JPOXMLDOC01-appb-T000068
Figure JPOXMLDOC01-appb-T000068
Figure JPOXMLDOC01-appb-T000069
Figure JPOXMLDOC01-appb-T000069
Figure JPOXMLDOC01-appb-T000070
Figure JPOXMLDOC01-appb-T000070
Figure JPOXMLDOC01-appb-T000071
Figure JPOXMLDOC01-appb-T000071
Figure JPOXMLDOC01-appb-T000072
Figure JPOXMLDOC01-appb-T000072
Figure JPOXMLDOC01-appb-T000073
Figure JPOXMLDOC01-appb-T000073
Figure JPOXMLDOC01-appb-T000074
Figure JPOXMLDOC01-appb-T000074
Figure JPOXMLDOC01-appb-T000075
Figure JPOXMLDOC01-appb-T000075
Figure JPOXMLDOC01-appb-T000076
Figure JPOXMLDOC01-appb-T000076
　一方、一般式［Ｉ］で表される本発明の化合物は、以下に示す製造法に従って製造することができるが、これらの方法に限定されるものではない。尚、以下、例えば「一般式［Ｉ－１］で表される化合物」及び「化合物［Ｉ－１］」は同意とする。 On the other hand, the compound of the present invention represented by the general formula [I] can be produced according to the following production methods, but is not limited to these methods. Hereinafter, for example, “the compound represented by the general formula [I-1]” and “the compound [I-1]” are synonymous.
＜製造方法１＞
　本発明の化合物のうち、一般式［Ｉ－１］で表される化合物は、例えば一般式［ＩＩＩ－１］で表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Production method 1>
Among the compounds of the present invention, the compound represented by the general formula [I-1] can be produced, for example, using a compound represented by the general formula [III-1] according to a method comprising the following reaction formula. Can be.
Figure JPOXMLDOC01-appb-C000077
Figure JPOXMLDOC01-appb-C000077
　（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｋ及びｎは前記と同じ意味を示し、Ｒａは水素原子、ハロゲン原子、シアノ基、－Ｃ（＝Ｏ）Ｋ又は－Ｃ（＝Ｏ）ＮＲ１Ｒ２を示し、Ｌ１はハロゲン原子を示し、Ｌ２はＣ１～Ｃ６アルコキシ基又はＣ１～Ｃ６アルキルチオ基を示し、ＲｂはＣ１～Ｃ６アルキル基等を示す。） (Wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , K and n have the same meaning as described above, and Ra is a hydrogen atom, a halogen atom, a cyano group, —C (＝ O ) Represents K or —C (ＯO) NR 1 R 2 , L 1 represents a halogen atom, L 2 represents a C 1 -C 6 alkoxy group or a C 1 -C 6 alkylthio group, and R b represents C 1 Represents a C 6 alkyl group, etc.)
　（工程１－１）
　即ち、一般式［Ｉ－１］で表される化合物は、一般式［ＩＩＩ－１］で表される化合物と化合物［ＩＶ－１］又は化合物［ＩＶ－２］とを、適当な塩基の存在下、適当な溶媒中において反応させることにより製造することができる。
　本工程で使用する化合物［ＩＶ－１］又は化合物［ＩＶ－２］の使用量は、化合物［ＩＩＩ－１］１モルに対して１モルから溶媒量相当の範囲から適宜選択すればよく、好ましくは１．０～２．０モルである。
　本工程で使用できる塩基は、例えば、水酸化ナトリウム、水酸化カリウム、水酸化リチウム等のアルカリ金属の水酸化物類、水酸化カルシウム、水酸化マグネシウム等のアルカリ土類金属の水酸化物類、炭酸ナトリウム、炭酸カリウム等のアルカリ金属の炭酸塩類、炭酸水素ナトリウム、炭酸水素カリウム等のアルカリ金属の重炭酸塩類等の無機塩基類、水素化ナトリウム、水素化カリウム等の金属水素化物類、ナトリウムメトキシド、ナトリウムエトキシド、カリウムｔｅｒｔ－ブトキシド等のアルコールの金属塩類、又はトリエチルアミン、Ｎ，Ｎ－ジメチルアニリン、ピリジン、４－Ｎ，Ｎ－ジメチルアミノピリジン、１，８－ジアザビシクロ［５，４，０］－７－ウンデセン等の有機塩基類等が挙げられる。尚、塩基の使用量は、化合物［ＩＩＩ－１］１モルに対して１～５モルの範囲から適宜選択すればよく、好ましくは１．０～３．０モルである。
　本工程で使用できる溶媒としては、例えば、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、メタノール、エタノール、２－プロパノール等のアルコール類、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、酢酸エチル等のエステル類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類、ピリジン、ピコリン等のピリジン類又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［ＩＩＩ－１］１モルに対して０．１～１００リットルであり、好ましくは０．３～１０リットルである。
　本工程の反応温度は、０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは０℃～１５０℃の範囲で行うのがよい。
　本工程の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１５分～２４時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［Ｉ－１］を単離することができる。単離した化合物［Ｉ－１］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 1-1)
That is, the compound represented by the general formula [I-1] is obtained by converting the compound represented by the general formula [III-1] and the compound [IV-1] or the compound [IV-2] into an appropriate base. It can be produced by reacting in an appropriate solvent below.
The amount of compound [IV-1] or compound [IV-2] used in this step may be appropriately selected from the range of 1 mol to the amount of solvent relative to 1 mol of compound [III-1], and is preferably used. Is 1.0 to 2.0 mol.
Bases that can be used in this step include, for example, hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide and lithium hydroxide, hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide, Inorganic bases such as alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydrides such as sodium hydride and potassium hydride; sodium methoxy Metal salts of alcohols such as sodium, sodium ethoxide and potassium tert-butoxide, or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5,4,0 And organic bases such as -7-undecene. The amount of the base used may be appropriately selected from the range of 1 to 5 mol per 1 mol of the compound [III-1], and is preferably 1.0 to 3.0 mol.
Examples of the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone, methanol, ethanol , Alcohols such as 2-propanol, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, esters such as ethyl acetate, aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane, pyridine, Pi Pyridines or a mixture solvent thereof phosphorus, and the like. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-1].
The reaction temperature in this step may be selected from an arbitrary temperature range from 0 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 150 ° C.
The reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 15 minutes to 24 hours.
After completion of the reaction, compound [I-1] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., if necessary.
　（工程１－２）
　また、一般式［Ｉ－１］で表される化合物は、一般式［ＩＩＩ－１］で表される化合物とアミノ化剤とを反応させることによって一般式［ＩＩＩ－２］で表される化合物を製造し、この化合物［ＩＩＩ－２］と化合物［ＩＶ－３］又は化合物［ＩＶ－４］とを、適当な塩基の存在下又は非存在下、適当な酸触媒の存在下又は非存在下、適当な溶媒中において反応させることにより製造することができる。
　本工程で使用できるアミノ化剤としては、例えば、アンモニア、アンモニア水等が挙げられる。尚、アミノ化剤の使用量は、化合物［ＩＩＩ－１］１モルに対して１～３０モルの範囲から適宜選択すればよく、好ましくは１．０～２５．０モルである。
　本工程で使用できる溶媒としては、例えば、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、メタノール、エタノール、２－プロパノール等のアルコール類、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、酢酸エチル等のエステル類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類、ピリジン、ピコリン等のピリジン類又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［ＩＩＩ－１］１モルに対して０．１～１００リットルであり、好ましくは０．３～１０リットルである。
　本工程の反応温度は、－３０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは－１０℃～１００℃の範囲で行うのがよい。
　本工程の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１５分～２４時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［ＩＩＩ－２］を単離することができる。単離した化合物［ＩＩＩ－２］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 1-2)
The compound represented by the general formula [I-1] is obtained by reacting the compound represented by the general formula [III-1] with an aminating agent. And then reacting the compound [III-2] with the compound [IV-3] or the compound [IV-4] in the presence or absence of a suitable base, in the presence or absence of a suitable acid catalyst. In a suitable solvent.
Examples of the aminating agent that can be used in this step include ammonia, aqueous ammonia, and the like. The amount of the aminating agent may be appropriately selected from the range of 1 to 30 mol per 1 mol of the compound [III-1], and is preferably 1.0 to 25.0 mol.
Examples of the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like Aprotic polar solvents, alcohols such as methanol, ethanol and 2-propanol, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, esters such as ethyl acetate, pentane, hexane, cyclohexyl Emissions, aliphatic hydrocarbons such as heptane, pyridine, pyridine or a mixed solvent of these picoline, and the like. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-1].
The reaction temperature in this step may be selected from an arbitrary temperature range from −30 ° C. to the reflux temperature in the reaction system, and is preferably from −10 ° C. to 100 ° C.
The reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 15 minutes to 24 hours.
After completion of the reaction, compound [III-2] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [III-2] can be further purified, if necessary, by column chromatography, recrystallization and the like.
　（工程１－３）
　本工程で使用する化合物［ＩＶ－３］又は化合物［ＩＶ－４］の使用量は、化合物［ＩＩＩ－２］１モルに対して１モルから溶媒量相当の範囲から適宜選択すればよく、好ましくは１．０～１０．０モルである。但し、化合物［ＩＶ－４］は、上記の溶媒として使用することもできる。
　本工程で酸触媒を使用する場合、使用できる酸触媒は、例えば、メタンスルホン酸又はｐ－トルエンスルホン酸等のスルホン酸類、塩酸、臭化水素酸又は硫酸等の鉱酸類、酢酸又はトリフルオロ酢酸等のカルボン酸類等が挙げられる。尚、酸触媒の使用量は、化合物［ＩＩＩ－２］１モルに対して０．０１モルから１０モルの範囲から適宜選択すればよく、好ましくは０．０５～１．０モルである。
　本工程で塩基を使用する場合、使用できる塩基は、例えば、水酸化ナトリウム、水酸化カリウム、水酸化リチウム等のアルカリ金属の水酸化物類、水酸化カルシウム、水酸化マグネシウム等のアルカリ土類金属の水酸化物類、炭酸ナトリウム、炭酸カリウム等のアルカリ金属の炭酸塩類、炭酸水素ナトリウム、炭酸水素カリウム等のアルカリ金属の重炭酸塩類等の無機塩基類、水素化ナトリウム、水素化カリウム等の金属水素化物類、ナトリウムメトキシド、ナトリウムエトキシド、カリウムｔｅｒｔ－ブトキシド等のアルコールの金属塩類、又はトリエチルアミン、Ｎ，Ｎ－ジメチルアニリン、ピリジン、４－Ｎ，Ｎ－ジメチルアミノピリジン、１，８－ジアザビシクロ［５，４，０］－７－ウンデセン等の有機塩基類等が挙げられる。尚、塩基の使用量は、化合物［ＩＩＩ－２］１モルに対して１モルから溶媒量相当の範囲から適宜選択すればよく、好ましくは１．０～１．５モルである。
　本工程で使用できる溶媒としては、例えば、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、メタノール、エタノール、２－プロパノール等のアルコール類、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、酢酸エチル等のエステル類、ペンタン、ヘキサン、シクロヘキサン及び、ヘプタン等の脂肪族炭化水素類、ピリジン、ピコリン等のピリジン類、オルトギ酸トリメチル、オルトギ酸トリエチル、オルト酢酸トリメチル、オルト酢酸トリエチル等のオルトエステル類又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［ＩＩＩ－２］１モルに対して０．１～１００リットルであり、好ましくは０．３～１０リットルである。
　本工程の反応温度は、－３０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは－１０℃～１００℃の範囲で行うのがよい。
　本工程の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１５分～２４時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［Ｉ－１］を単離することができる。単離した化合物［Ｉ－１］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 1-3)
The amount of compound [IV-3] or compound [IV-4] used in this step may be appropriately selected from the range of 1 mol to the amount of solvent relative to 1 mol of compound [III-2], and is preferably used. Is 1.0 to 10.0 mol. However, compound [IV-4] can also be used as the above solvent.
When an acid catalyst is used in this step, usable acid catalysts include, for example, sulfonic acids such as methanesulfonic acid or p-toluenesulfonic acid, mineral acids such as hydrochloric acid, hydrobromic acid or sulfuric acid, acetic acid or trifluoroacetic acid. And the like. The amount of the acid catalyst used may be appropriately selected from the range of 0.01 mol to 10 mol per 1 mol of the compound [III-2], and is preferably 0.05 to 1.0 mol.
When a base is used in this step, usable bases include, for example, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, and alkaline earth metals such as calcium hydroxide and magnesium hydroxide. Hydroxides, alkali metal carbonates such as sodium carbonate and potassium carbonate, inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, and metals such as sodium hydride and potassium hydride Metal salts of alcohols such as hydrides, sodium methoxide, sodium ethoxide, potassium tert-butoxide, or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo Organic bases such as [5,4,0] -7-undecene. The amount of the base used may be appropriately selected from the range of 1 mol to the amount of solvent relative to 1 mol of compound [III-2], and is preferably from 1.0 to 1.5 mol.
Examples of the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like Aprotic polar solvents, alcohols such as methanol, ethanol and 2-propanol, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, esters such as ethyl acetate, pentane, hexane, cyclohexyl Emissions and, aliphatic hydrocarbons such as heptane, pyridine, pyridine picoline, etc., trimethyl orthoformate, triethyl orthoformate, trimethyl orthoacetate, ortho esters or mixtures of these solvents, such as triethyl orthoacetate and the like. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-2].
The reaction temperature in this step may be selected from an arbitrary temperature range from −30 ° C. to the reflux temperature in the reaction system, and is preferably from −10 ° C. to 100 ° C.
The reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 15 minutes to 24 hours.
After completion of the reaction, compound [I-1] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., if necessary.
＜製造方法２＞
　本発明の化合物のうち、一般式［Ｉ－１］で表される化合物及び一般式［Ｉ－２］で表される化合物は、例えば一般式［ＩＩＩ－３］で表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Production method 2>
Among the compounds of the present invention, the compound represented by the general formula [I-1] and the compound represented by the general formula [I-2] can be obtained by using, for example, a compound represented by the general formula [III-3]. It can be produced according to a method comprising the following reaction formula.
Figure JPOXMLDOC01-appb-C000078
Figure JPOXMLDOC01-appb-C000078
　（式中、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒａ及びｎは前記と同じ意味を示し、Ｌ３はハロゲン原子、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、フェニルオキシ基、Ｃ１～Ｃ６アルキルチオ基又はＣ１～Ｃ６ハロアルキルチオ基を示す。） (Wherein, R 3 , R 4 , R 5 , R 6 , R a and n have the same meaning as described above, and L 3 is a halogen atom, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkoxy group. , A phenyloxy group, a C 1 -C 6 alkylthio group or a C 1 -C 6 haloalkylthio group.)
　（工程２－１）
　即ち、一般式［Ｉ－１］で表される化合物は、化合物［ＩＶ－５］と酸ハロゲン化物及び酸無水物等から誘導される化合物［ＩＶ－６］と一般式［ＩＩＩ－３］で表される化合物とを、適当な酸の存在下又は非存在下、適当な溶媒中において反応させることにより製造することができる。
　本工程で使用する化合物［ＩＶ－６］の使用量は、化合物［ＩＩＩ－３］１モルに対して１～５モルの範囲から適宜選択すればよく、好ましくは１．０～２．５モルである。
　本工程で酸を使用する場合、使用できる酸は、例えば、メタンスルホン酸又はｐ－トルエンスルホン酸等のスルホン酸類、塩酸、臭化水素酸又は硫酸等の鉱酸類、酢酸又はトリフルオロ酢酸等のカルボン酸類等が挙げられる。尚、酸の使用量は化合物［ＩＩＩ－３］１モルに対して０．００１～１０モルの範囲から適宜選択すればよく、好ましくは０．００１～３．０モルである。
　本工程で使用できる溶媒としては、例えば、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、メタノール、エタノール、２－プロパノール等のアルコール類、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類、水又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［ＩＩＩ－３］１モルに対して０．１～１００リットルであり、好ましくは０．３～１０リットルである。
　本工程の反応温度は、－３０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは－１０℃～１００℃の範囲で行うのがよい。
　本工程の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１０分～２０時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［Ｉ－１］を単離することができる。単離した化合物［Ｉ－１］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 2-1)
That is, the compound represented by the general formula [I-1] includes the compound [IV-5], the compound [IV-6] derived from an acid halide and an acid anhydride, and the general formula [III-3]. The compound can be produced by reacting the compound represented with a suitable solvent in the presence or absence of a suitable acid in a suitable solvent.
The amount of compound [IV-6] used in this step may be appropriately selected from the range of 1 to 5 mol per 1 mol of compound [III-3], and is preferably 1.0 to 2.5 mol. It is.
When an acid is used in this step, examples of the acid that can be used include sulfonic acids such as methanesulfonic acid or p-toluenesulfonic acid, mineral acids such as hydrochloric acid, hydrobromic acid and sulfuric acid, and acetic acid and trifluoroacetic acid. And carboxylic acids. The amount of the acid to be used may be appropriately selected from the range of 0.001 to 10 mol, preferably 0.001 to 3.0 mol, per 1 mol of compound [III-3].
Examples of the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like Aprotic polar solvents, alcohols such as methanol, ethanol, 2-propanol, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and aliphatic carbons such as pentane, hexane, cyclohexane, heptane Hydrogen such as water or a mixed solvent thereof. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-3].
The reaction temperature in this step may be selected from an arbitrary temperature range from −30 ° C. to the reflux temperature in the reaction system, and is preferably from −10 ° C. to 100 ° C.
The reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 10 minutes to 20 hours.
After completion of the reaction, compound [I-1] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., if necessary.
　（工程２－２）
　また、一般式［Ｉ－２］で表される化合物は、化合物［ＩＶ－７］と二硫化炭素とハロゲン化アルキル等から誘導される化合物［ＩＶ－８］と一般式［ＩＩＩ－３］で表される化合物とを、適当な溶媒中において反応させることにより製造することができる。
　本工程で使用する化合物［ＩＶ－８］の使用量は、化合物［ＩＩＩ－３］１モルに対して１～１０モルの範囲から適宜選択すればよく、好ましくは１．０～１．５モルである。
　本工程で使用できる溶媒としては、例えば、前記工程３で説明した同様の溶媒を挙げることができる。尚、溶媒の使用量は、化合物［ＩＩＩ－３］１モルに対して０．１～１００リットルであり、好ましくは０．３～１０リットルである。
　本工程の反応温度は、－３０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは－１０℃～１００℃の範囲で行うのがよい。
　本工程の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１０分～２０時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［Ｉ－２］を単離することができる。または反応混合物から溶媒を濃縮する事でも化合物［Ｉ－２］を単離することができる。単離した化合物［Ｉ－２］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 2-2)
In addition, the compound represented by the general formula [I-2] includes a compound [IV-7], a compound [IV-8] derived from carbon disulfide, an alkyl halide and the like, and a compound [IV-3]. The compound can be produced by reacting the compound represented with the compound in a suitable solvent.
The amount of compound [IV-8] used in this step may be appropriately selected from the range of 1 to 10 mol per 1 mol of compound [III-3], and is preferably 1.0 to 1.5 mol. It is.
As the solvent that can be used in this step, for example, the same solvent as described in Step 3 can be exemplified. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-3].
The reaction temperature in this step may be selected from an arbitrary temperature range from −30 ° C. to the reflux temperature in the reaction system, and is preferably from −10 ° C. to 100 ° C.
The reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 10 minutes to 20 hours.
After completion of the reaction, compound [I-2] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. Alternatively, compound [I-2] can also be isolated by concentrating the solvent from the reaction mixture. The isolated compound [I-2] can be further purified, if necessary, by column chromatography, recrystallization and the like.
＜製造方法３＞
　本発明の化合物のうち、一般式［Ｉ－４］で表される化合物、一般式［Ｉ－５］で表される化合物及び一般式［Ｉ－６］で表される化合物は、例えば一般式［Ｉ－３］表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Production method 3>
Among the compounds of the present invention, the compound represented by the general formula [I-4], the compound represented by the general formula [I-5] and the compound represented by the general formula [I-6] include, for example, It can be produced using the compound represented by [I-3] according to a method comprising the following reaction formula.
Figure JPOXMLDOC01-appb-C000079
Figure JPOXMLDOC01-appb-C000079
　（式中、Ｒ３、Ｒ４、Ｒ６、Ｒ１３、Ｒａ、Ｚ、ｐ１及びｎは前記と同じ意味を示し、Ｍはアルカリ金属又はアルカリ土類金属を示し、好ましいアルカリ金属としてはナトリウム又はカリウムが挙げることができ、Ｒ５ａはＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニル基、芳香族複素環又は飽和複素環を示す。）
　即ち、一般式［Ｉ－４］で表される化合物、一般式［Ｉ－５］で表される化合物及び一般式［Ｉ－６］で表される化合物は、化合物［Ｉ－３］を、適当な溶媒中、Organic　Syntheses, Coll. Vol.3, p.185(1955)に記載の方法に準じて（例えば、塩酸及び硫酸等の鉱酸と亜硝酸塩又は亜硝酸アルキルエステルを用いる方法により）ジアゾニウム塩とした後、化合物［ＩＶ－９］で表されるメルカプタンの塩、化合物［ＩＶ－１０］で表されるジスルフィド類又はハロゲン化銅の存在下又は非存在下、適当な溶媒中において反応させることによりそれぞれ製造することができる。 (Wherein, R 3 , R 4 , R 6 , R 13 , R a , Z, p 1 and n have the same meaning as described above, M represents an alkali metal or an alkaline earth metal, and preferred alkali metals are can be exemplified sodium or potassium, substituted R 5a is C 1 ~ C 6 alkyl group, C 1 ~ C 6 haloalkyl group, C 1 ~ C 6 alkyl group optionally substituted by R 13, optionally by R 13 C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halo A cycloalkyl group, a phenyl group unsubstituted or substituted by (Z) p 1 , an aromatic heterocycle or a saturated heterocycle.)
That is, the compound represented by the general formula [I-4], the compound represented by the general formula [I-5] and the compound represented by the general formula [I-6] are obtained by converting the compound [I-3] into In a suitable solvent, according to the method described in Organic Syntheses, Coll. Vol. 3, p. 185 (1955) (for example, by using a mineral acid such as hydrochloric acid and sulfuric acid and a nitrite or an alkyl nitrite). After converting into a diazonium salt, the reaction is carried out in a suitable solvent in the presence or absence of a mercaptan salt represented by the compound [IV-9], a disulfide represented by the compound [IV-10] or a copper halide. By doing so, they can be manufactured respectively.
　（工程３－１）
　本工程で使用する化合物［ＩＶ－９］又は化合物［ＩＶ－１０］の使用量は、化合物［Ｉ－３］１モルに対して１～５モルの範囲から適宜選択すればよく、好ましくは１．０～２．０モルである。
　本工程で使用できる溶媒としては、例えば、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、塩酸、硫酸等の鉱酸類、酢酸等のカルボン酸類、水又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［Ｉ－３］１モルに対して０．１～１００リットルであり、好ましくは０．３～１０リットルである。
　本工程の反応温度は、－７０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは－２０℃～１００℃の範囲で行うのがよい。
　本工程の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１０分～２４時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物[Ｉ－４]を単離することができる。単離した化合物[Ｉ－４]は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 3-1)
The amount of compound [IV-9] or compound [IV-10] used in this step may be appropriately selected from the range of 1 to 5 mol per 1 mol of compound [I-3], and is preferably 1 0.0 to 2.0 mol.
Examples of the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl Examples include aprotic polar solvents such as sulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone, mineral acids such as hydrochloric acid and sulfuric acid, carboxylic acids such as acetic acid, water, and a mixed solvent thereof. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [I-3].
The reaction temperature in this step may be selected from an arbitrary temperature range from −70 ° C. to the reflux temperature in the reaction system, and is preferably from −20 ° C. to 100 ° C.
The reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually from 10 minutes to 24 hours.
After completion of the reaction, compound [I-4] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-4] can be further purified, if necessary, by column chromatography, recrystallization and the like.
　（工程３－２）
　本工程で使用できるハロゲン化銅としては、例えば、塩化銅（Ｉ）、臭化銅（Ｉ）、ヨウ化銅（Ｉ）、塩化銅（ＩＩ）、臭化銅（ＩＩ）等を挙げることができる。尚、ハロゲン化銅の使用量は、化合物［Ｉ－３］１モルに対して０～５モルの範囲から適宜選択すればよく、好ましくは１．０～２．５モルである。
　本工程で使用できる溶媒、反応温度及び反応時間は、工程３－１と同様である。
　反応終了後は、反応混合物を水に注加し中和した後、析出した固体を濾取する又は有機溶媒にて抽出してから濃縮する等の操作を行うことにより、化合物［Ｉ－５］を単離することができる。単離した化合物［Ｉ－５］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 3-2)
Examples of the copper halide that can be used in this step include copper (I) chloride, copper (I) bromide, copper (I) iodide, copper (II) chloride, copper (II) bromide, and the like. it can. The amount of the copper halide to be used may be appropriately selected from the range of 0 to 5 mol per 1 mol of the compound [I-3], and is preferably 1.0 to 2.5 mol.
The solvent, reaction temperature, and reaction time that can be used in this step are the same as those in Step 3-1.
After completion of the reaction, the reaction mixture is poured into water to neutralize, and then the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to obtain the compound [I-5]. Can be isolated. The isolated compound [I-5] can be further purified, if necessary, by column chromatography, recrystallization and the like.
　（工程３－３）
　本工程で使用できる溶媒としては、例えば、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、アセトニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［Ｉ－３］１モルに対して０．１～１００リットルであり、好ましくは０．３～３０リットルである。
　本工程の反応温度及び反応時間は、工程３－１と同様である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物[Ｉ－６]を単離することができる。または反応混合物から溶媒を濃縮する事でも化合物［Ｉ－６］を単離することができる。単離した化合物[Ｉ－６]は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 3-3)
Examples of the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, nitriles such as acetonitrile and propionitrile, and N, N-dimethyl. Aprotic polar solvents such as formamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone, and a mixed solvent thereof; . The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-30 liters, per 1 mol of compound [I-3].
The reaction temperature and reaction time in this step are the same as in Step 3-1.
After completion of the reaction, compound [I-6] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. Alternatively, compound [I-6] can be isolated by concentrating the solvent from the reaction mixture. The isolated compound [I-6] can be further purified by column chromatography, recrystallization, or the like, if necessary.
＜製造方法４＞
　本発明の化合物のうち、一般式［Ｉ－８］で表される化合物は、例えば一般式［Ｉ－７］表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Production method 4>
Among the compounds of the present invention, the compound represented by the general formula [I-8] can be produced, for example, using a compound represented by the general formula [I-7] according to a method comprising the following reaction formula. it can.
Figure JPOXMLDOC01-appb-C000080
Figure JPOXMLDOC01-appb-C000080
　（式中、Ｒ３、Ｒ４、Ｒ５ａ、Ｒ６、Ｒａ及びｎは前記と同じ意味を示し、ｍは１又は２の整数を示す。）
　即ち、一般式［Ｉ－８］で表される化合物は、化合物［Ｉ－７］と酸化剤とを、適当な触媒の存在下又は非存在下、適当な溶媒中において反応させることにより製造することができる。
　本反応で使用できる酸化剤としては、例えば、過酸化水素、ｍ－クロロ過安息香酸、過ヨウ素酸ナトリウム、オキソン（ＯＸＯＮＥ、イー・アイ・デュポン社商品名；ペルオキソ硫酸水素カリウム含有物）、Ｎ－クロロコハク酸イミド、Ｎ－ブロモコハク酸イミド、次亜塩素酸ｔｅｒｔ－ブチル、次亜塩素酸ナトリウム等を挙げることができる。尚、酸化剤の使用量は、一般式［Ｉ－８］で表される化合物の硫黄原子の酸化数ｍに依存するが、化合物［Ｉ－７］１モルに対して１～５モルの範囲から適宜選択すればよく、好ましくは１．０～２．５モルである。
　本反応で使用できる触媒としては、例えば、タングステン酸ナトリウム等を挙げることができる。尚、触媒の使用量は、化合物［Ｉ－７］１モルに対して０．０１～１モルの範囲から適宜選択すればよく、好ましくは０．０１～０．１モルである。
　本反応で使用できる溶媒としては、例えば、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、メタノール、エタノール、２－プロパノール等のアルコール類、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類、酢酸、水又はこれらの混合溶媒等を挙げることができる。尚、溶媒の使用量は、化合物［Ｉ－７］１モルに対して０．１～１００リットルであり、好ましくは０．３～１５リットルである。
　本反応の反応温度は、通常－３０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは－１０℃～１００℃の範囲で行うのがよい。
　本反応の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１０分～２４時間である。
　反応終了後は、反応混合物を水等に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［Ｉ－８］を単離することができる。単離した化合物［Ｉ－８］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (In the formula, R 3 , R 4 , R 5a , R 6 , R a and n have the same meaning as described above, and m represents an integer of 1 or 2.)
That is, the compound represented by the general formula [I-8] is produced by reacting the compound [I-7] with an oxidizing agent in an appropriate solvent in the presence or absence of an appropriate catalyst. be able to.
Examples of the oxidizing agent that can be used in this reaction include hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, oxone (OXONE, trade name of EI DuPont; products containing potassium hydrogen peroxosulfate), N -Chlorosuccinimide, N-bromosuccinimide, tert-butyl hypochlorite, sodium hypochlorite and the like. The amount of the oxidizing agent depends on the oxidation number m of the sulfur atom of the compound represented by the general formula [I-8], but is in the range of 1 to 5 mol per 1 mol of the compound [I-7]. And it may be appropriately selected from the above, preferably from 1.0 to 2.5 mol.
Examples of the catalyst that can be used in this reaction include sodium tungstate. The amount of the catalyst to be used may be appropriately selected from the range of 0.01 to 1 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound [I-7].
Solvents that can be used in this reaction include, for example, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide Aprotic polar solvents such as benzene, sulfolane, 1,3-dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol and 2-propanol; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane And aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane, acetic acid, water and a mixed solvent thereof. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-15 liters, per 1 mol of compound [I-7].
The reaction temperature of this reaction may be selected from an arbitrary temperature range usually from −30 ° C. to the reflux temperature in the reaction system, and is preferably from −10 ° C. to 100 ° C.
The reaction time of this reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually from 10 minutes to 24 hours.
After completion of the reaction, the compound [I-8] can be isolated by pouring the reaction mixture into water or the like, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-8] can be further purified, if necessary, by column chromatography, recrystallization and the like.
＜製造方法５＞
　本発明の化合物のうち、一般式［Ｉ－１１］で表される化合物は、例えば一般式［Ｉ－９］表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Production method 5>
Among the compounds of the present invention, the compound represented by the general formula [I-11] can be produced, for example, using a compound represented by the general formula [I-9] according to a method comprising the following reaction formula. it can.
Figure JPOXMLDOC01-appb-C000081
Figure JPOXMLDOC01-appb-C000081
　（式中、Ｒ３、Ｒ４、Ｒ６、Ｒａ及びｎは前記と同じ意味を示し、Ｒｃはメチル基又はトリフルオロメチル基を示す。）
　即ち、一般式［Ｉ－１１］で表される化合物は、化合物［Ｉ－９］を無水酢酸又は無水トリフルオロ酢酸と反応させることにより化合物［Ｉ－１０］を製造し、続いて化合物［Ｉ－１０］を適当な塩基又は適当な酸の存在下、適当な溶媒中において加水分解することにより、製造することができる。
　本反応で使用する無水酢酸又は無水トリフルオロ酢酸の使用量は、化合物［Ｉ－９］１モルに対して１モルから溶媒量相当の範囲から選択すればよく、好ましくは１．０～７．０モルである。
　本反応で使用できる溶媒としては、例えば、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、メタノール、エタノール、２－プロパノール等のアルコール類、アセトニトリル、プロピオニトリル等のニトリル類、酢酸エチル等のエステル類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類、水又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［Ｉ－９］１モルに対して０．１～１００リットルであり、好ましくは０．３～１０リットルである。
　本反応で塩基を使用する場合、使用できる塩基は、例えば、水酸化リチウム、水酸化ナトリウム、水酸化カリウム等のアルカリ金属の水酸化物類、水酸化カルシウム、水酸化マグネシウム等のアルカリ土類金属の水酸化物類、炭酸ナトリウム、炭酸カリウム等のアルカリ金属の炭酸塩類等の無機塩基類、ナトリウムメトキシド、ナトリウムエトキシド、カリウムｔｅｒｔ－ブトキシド等のアルコールの金属塩類又はトリエチルアミン、Ｎ，Ｎ－ジメチルアニリン、ピリジン、４－Ｎ，Ｎ－ジメチルアミノピリジン、１，８－ジアザビシクロ［５．４．０］－７－ウンデセン等の有機塩基類等が挙げられる。尚、塩基の使用量は、化合物［Ｉ－９］１モルに対して１～１０モルの範囲から適宜選択すればよく、好ましくは１．０～５．０モルである。
　本反応で酸を使用する場合、使用できる酸は、例えば、塩酸、臭化水素酸又は硫酸等の鉱酸類、酢酸又はトリフルオロ酢酸等のカルボン酸類等が挙げられる。尚、酸の使用量は化合物［Ｉ－９］１モルに対して１～溶媒量相当の範囲から適宜選択すればよく、好ましくは１～１００モルである。
　本反応の反応温度は、何れの反応においても－１０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは０℃～５０℃の温度範囲で行うのがよい。　
　本反応の反応時間は、何れの反応においても反応温度、反応基質、反応量等により異なるが、通常５分～２４時間である。
　反応終了後は、反応混合物を水等に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［Ｉ－１１］を単離することができる。単離した化合物［Ｉ－１１］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。また、化合物［Ｉ－１１］は、単離及び精製することなく次反応（製造方法６）に使用することもできる。 (In the formula, R 3 , R 4 , R 6 , R a and n have the same meaning as described above, and R c represents a methyl group or a trifluoromethyl group.)
That is, the compound represented by the general formula [I-11] is produced by reacting the compound [I-9] with acetic anhydride or trifluoroacetic anhydride to produce the compound [I-10], and then producing the compound [I-11]. -10] in a suitable solvent in the presence of a suitable base or a suitable acid.
The amount of acetic anhydride or trifluoroacetic anhydride to be used in this reaction may be selected from the range of 1 mol to the amount of a solvent relative to 1 mol of compound [I-9], and is preferably from 1.0 to 7.0. 0 mol.
Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; alcohols such as methanol, ethanol and 2-propanol; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate; pentane; Examples thereof include aliphatic hydrocarbons such as cyclohexane and heptane, water, and a mixed solvent thereof. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [I-9].
When a base is used in this reaction, usable bases include, for example, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metals such as calcium hydroxide and magnesium hydroxide. Hydroxides, inorganic bases such as alkali metal carbonates such as sodium carbonate and potassium carbonate, metal salts of alcohols such as sodium methoxide, sodium ethoxide and potassium tert-butoxide or triethylamine, N, N-dimethyl Organic bases such as aniline, pyridine, 4-N, N-dimethylaminopyridine, and 1,8-diazabicyclo [5.4.0] -7-undecene. The amount of the base to be used may be appropriately selected from the range of 1 to 10 mol per 1 mol of compound [I-9], and is preferably 1.0 to 5.0 mol.
When an acid is used in this reaction, usable acids include, for example, mineral acids such as hydrochloric acid, hydrobromic acid and sulfuric acid, and carboxylic acids such as acetic acid and trifluoroacetic acid. The amount of the acid to be used may be appropriately selected from the range of 1 to the amount of the solvent per 1 mol of the compound [I-9], and is preferably 1 to 100 mol.
The reaction temperature of this reaction may be selected from any temperature range from −10 ° C. to the reflux temperature in the reaction system in any reaction, and is preferably performed in a temperature range of 0 ° C. to 50 ° C.
The reaction time of this reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like in each reaction, but is usually 5 minutes to 24 hours.
After completion of the reaction, compound [I-11] can be isolated by pouring the reaction mixture into water or the like, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-11] can be further purified by column chromatography, recrystallization, and the like, if necessary. In addition, compound [I-11] can be used for the next reaction (Production method 6) without isolation and purification.
＜製造方法６＞
　本発明の化合物のうち、一般式［Ｉ－１２］で表される化合物は、例えば一般式［ＩＩＩ－３］で表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Manufacturing method 6>
Among the compounds of the present invention, the compound represented by the general formula [I-12] can be produced, for example, using a compound represented by the general formula [III-3] according to a method comprising the following reaction formula. Can be.
Figure JPOXMLDOC01-appb-C000082
Figure JPOXMLDOC01-appb-C000082
　（式中、Ｒ３、Ｒ４、Ｒ６、Ｒａ、Ｒｂ、Ｌ１、Ａ及びｎは前記と同じ意味を示す。）　 (In the formula, R 3 , R 4 , R 6 , R a , R b , L 1 , A and n have the same meaning as described above.)
　（工程６－１）
　即ち、一般式［Ｉ－１２］で表される化合物は、一般式［ＩＩＩ－３］で表される化合物とシアン酸塩又はチオシアン酸塩とを、適当な酸の存在下、適当な溶媒中において反応させ、一般式［ＩＩＩ－４］で表される化合物とした後、この化合物［ＩＩＩ－４］と化合物［ＩＶ－３］又は化合物［ＩＶ－４］とを、適当な塩基の存在下又は適当な酸触媒の存在下、適当な溶媒中において反応させることにより製造することができる。
　本反応で使用できるシアン酸塩又はチオシアン酸塩としては、例えば、シアン酸ナトリウム、シアン酸カリウム、シアン酸アンモニウム、チオシアン酸ナトリウム、チオシアン酸カリウム、チオシアン酸アンモニウム等が挙げられる。尚、シアン酸塩又はチオシアン酸塩の使用量は、化合物［ＩＩＩ－３］１モルに対して１モルから１０モルの範囲から選択すればよく、好ましくは１．０～６．０モルである。
　本工程で使用できる酸としては、例えば、塩酸又は臭化水素酸等の鉱酸類等が挙げられる。尚、酸の使用量は化合物［ＩＩＩ－４］１モルに対して１～溶媒量相当の範囲から適宜選択すればよく、好ましくは１．０～１０．０モルである。
　本工程で使用できる溶媒としては、例えば、アセトニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、メタノール、エタノール、２－プロパノール等のアルコール類、水又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［ＩＩＩ－３］１モルに対して０．１～１００リットルであり、好ましくは０．３～１０リットルである。
　本工程の反応温度は、－３０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは－１０℃～１００℃の範囲で行うのがよい。
　本工程の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１０分～２０時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［Ｉ－１２］を単離することができる。単離した化合物［Ｉ－１２］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 6-1)
That is, the compound represented by the general formula [I-12] is prepared by combining the compound represented by the general formula [III-3] with a cyanate or thiocyanate in a suitable solvent in the presence of a suitable acid. And converting the compound [III-4] to the compound [IV-3] or the compound [IV-4] in the presence of a suitable base. Alternatively, it can be produced by reacting in a suitable solvent in the presence of a suitable acid catalyst.
Examples of the cyanate or thiocyanate that can be used in this reaction include sodium cyanate, potassium cyanate, ammonium cyanate, sodium thiocyanate, potassium thiocyanate, and ammonium thiocyanate. The amount of the cyanate or thiocyanate to be used may be selected from the range of 1 mol to 10 mol per 1 mol of the compound [III-3], and is preferably 1.0 to 6.0 mol. .
Examples of the acid that can be used in this step include mineral acids such as hydrochloric acid and hydrobromic acid. The amount of the acid used may be appropriately selected from the range of 1 to the amount of the solvent based on 1 mol of the compound [III-4], and is preferably from 1.0 to 10.0 mol.
Examples of the solvent that can be used in this step include nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, Examples include aprotic polar solvents such as 3-dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol and 2-propanol, water or a mixed solvent thereof. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-3].
The reaction temperature in this step may be selected from an arbitrary temperature range from −30 ° C. to the reflux temperature in the reaction system, and is preferably from −10 ° C. to 100 ° C.
The reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 10 minutes to 20 hours.
After completion of the reaction, compound [I-12] can be isolated by performing an operation such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-12] can be further purified by column chromatography, recrystallization or the like, if necessary.
　（工程６－２）
　一般式［Ｉ－１２］で表される化合物は、一般式［ＩＩＩ－４］で表される化合物を、製造方法１の工程１－３と同様な条件を用いて反応させることにより製造することができる。 (Step 6-2)
The compound represented by the general formula [I-12] is produced by reacting the compound represented by the general formula [III-4] under the same conditions as in step 1-3 of production method 1. Can be.
＜製造方法７＞
　本発明の化合物のうち、一般式［Ｉ－１４］で表される化合物は、例えば一般式［Ｉ－１３］で表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Production method 7>
Among the compounds of the present invention, the compound represented by the general formula [I-14] can be produced, for example, using a compound represented by the general formula [I-13] according to a method comprising the following reaction formula. Can be.
Figure JPOXMLDOC01-appb-C000083
Figure JPOXMLDOC01-appb-C000083
　（式中、Ｒ３、Ｒ４、Ｒ５ａ、Ｒ６、Ｒ１０、Ｒａ、Ｒｂ及びｎは前記と同じ意味を示し、Ｙは酸素原子、硫黄原子又はＮＲ１０を示し、Ｌ４はハロゲン原子、メタンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基、ノナフルオロブタンスルホニルオキシ基、ベンゼンスルホニルオキシ基、ｐ－トルエンスルホニルオキシ基又は－Ｓ（＝Ｏ）２Ｒｂを示し、Ｒ５ｂはフッ素原子、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルキル基又はＣ１～Ｃ６ハロアルコキシ基を示す。）
　即ち、一般式［Ｉ－１４］で表される化合物は、一般式［Ｉ－１３］で表される化合物と化合物［ＩＶ－１１］又は化合物［ＩＶ－１２］とを、適当な塩基の存在下又は非存在下、適当なラジカル開始剤の存在下又は非存在下、適当な溶媒中において反応させることにより製造することができる。
　本反応で使用する化合物［ＩＶ－１１］又は化合物［ＩＶ－１２］の使用量は、化合物［Ｉ－１３］１モルに対して１～２０モルの範囲から適宜選択すればよく、好ましくは１．１～５．５モルである。
　本反応で使用できる塩基は、例えば、水酸化ナトリウム、水酸化カリウム、水酸化リチウム等のアルカリ金属の水酸化物類、水酸化カルシウム、水酸化マグネシウム等のアルカリ土類金属の水酸化物類、炭酸ナトリウム、炭酸カリウム等のアルカリ金属の炭酸塩類、炭酸水素ナトリウム、炭酸水素カリウム等のアルカリ金属重炭酸塩類等の無機塩基類、水素化ナトリウム、水素化カリウム等の金属水素化物類、ナトリウムメトキシド、ナトリウムエトキシド、カリウムｔｅｒｔ－ブトキシド等のアルコールの金属塩類又はトリエチルアミン、Ｎ，Ｎ－ジメチルアニリン、ピリジン、４－Ｎ，Ｎ－ジメチルアミノピリジン、１，８－ジアザビシクロ［５．４．０］－７－ウンデセン等の有機塩基類等が挙げられる。尚、塩基の使用量は、化合物［Ｉ－１３］１モルに対して１～５モルの範囲から適宜選択すればよく、好ましくは１．０～２．０モルである。但し、トリエチルアミン、ピリジン等の有機塩基類は、上記の溶媒として使用することもできる。　本反応で使用できるラジカル開始剤は、例えば，亜硫酸、亜硫酸塩、ロンガリット（商品名、ナトリウムホルムアルデヒドスルホキシレ－ト）等の亜硫酸付加物等が挙げられる。尚、ラジカル開始剤の使用量は、化合物［Ｉ－１３］１モルに対して０．０１～５モルの範囲から適宜選択すればよく、好ましくは０．０１～１．２モルである。
　本反応で使用できる溶媒としては、例えば、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、メタノール、エタノール、２－プロパノール等のアルコール類、酢酸エチル等のエステル類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類、ピリジン、ピコリン等のピリジン類、トリエチルアミン、トリブチルアミン等の第三級アミン類、水又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［Ｉ－１３］１モルに対して０．１～１００リットルであり、好ましくは０．３～１０リットルである。
　本反応の反応温度は、－３０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは０℃～１５０℃の範囲で行うのがよい。
　本反応の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１０分～２０時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［Ｉ－１４］を単離することができる。単離した化合物［Ｉ－１４］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Wherein, R 3 , R 4 , R 5a , R 6 , R 10 , R a , R b and n have the same meaning as described above, Y represents an oxygen atom, a sulfur atom or NR 10 , and L 4 represents A halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a nonafluorobutanesulfonyloxy group, a benzenesulfonyloxy group, a p-toluenesulfonyloxy group, or —S (＝ O) 2 Rb , and R 5b is a fluorine atom , A C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkyl group or a C 1 -C 6 haloalkoxy group.)
That is, the compound represented by the general formula [I-14] is a compound represented by the general formula [I-13] and the compound [IV-11] or the compound [IV-12], The reaction can be carried out in a suitable solvent in the presence or absence of a suitable radical initiator in the presence or absence of a suitable radical initiator.
The amount of compound [IV-11] or compound [IV-12] used in this reaction may be appropriately selected from the range of 1 to 20 mol per 1 mol of compound [I-13], and is preferably 1 0.1 to 5.5 mol.
Bases that can be used in this reaction include, for example, hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide and lithium hydroxide, hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide, Inorganic bases such as alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, metal hydrides such as sodium hydride and potassium hydride, sodium methoxide , Sodium ethoxide, potassium tert-butoxide and other metal salts of alcohols or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0]- And organic bases such as 7-undecene. The amount of the base used may be appropriately selected from the range of 1 to 5 mol per 1 mol of the compound [I-13], and is preferably 1.0 to 2.0 mol. However, organic bases such as triethylamine and pyridine can also be used as the solvent. Examples of the radical initiator that can be used in this reaction include sulfurous acid, a sulfite, and a sulfurous acid adduct such as Rongalite (trade name, sodium formaldehyde sulfoxylate). The amount of the radical initiator to be used may be appropriately selected from the range of 0.01 to 5 mol per 1 mol of the compound [I-13], and is preferably 0.01 to 1.2 mol.
Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl Aprotic polar solvents such as sulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol, 2-propanol, esters such as ethyl acetate, pentane, hexane, cyclohexyl Emissions, aliphatic hydrocarbons such as heptane, pyridine, pyridine picoline such as triethylamine, tertiary amines such as tributylamine, water or a mixed solvent thereof. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [I-13].
The reaction temperature of this reaction may be selected from an arbitrary temperature range from −30 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 150 ° C.
The reaction time of this reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 10 minutes to 20 hours.
After completion of the reaction, compound [I-14] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-14] can be further purified, if necessary, by column chromatography, recrystallization and the like.
＜製造方法８＞
　本発明の化合物のうち、一般式［Ｉ－１５］で表される化合物、一般式［Ｉ－１６］で表される化合物及び一般式［Ｉ－１７］で表される化合物は、例えば一般式［Ｉ－２］で表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Production method 8>
Among the compounds of the present invention, the compound represented by the general formula [I-15], the compound represented by the general formula [I-16] and the compound represented by the general formula [I-17] include, for example, It can be produced using the compound represented by [I-2] according to a method comprising the following reaction formula.
Figure JPOXMLDOC01-appb-C000084
Figure JPOXMLDOC01-appb-C000084
　（式中、Ｒ３、Ｒ４、Ｒ５、Ｒａ、Ｍ、Ｌ１及びｎは前記と同じ意味を示し、Ｒ６ａはＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基又はＣ３～Ｃ６シクロアルキル基を示す。） (Wherein, R 3 , R 4 , R 5 , R a , M, L 1 and n have the same meanings as described above, and R 6a is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, Represents a 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group or a C 3 -C 6 cycloalkyl group.)
　（工程８－１）
　即ち、一般式［Ｉ－１５］で表される化合物は、一般式［Ｉ－２］で表される化合物を、製造方法３の工程３－１と同様な条件を用いて反応させることにより製造することができる。 (Step 8-1)
That is, the compound represented by the general formula [I-15] is produced by reacting the compound represented by the general formula [I-2] under the same conditions as in step 3-1 of the production method 3. can do.
　（工程８－２）
　また、一般式［Ｉ－１６］で表される化合物は、一般式［Ｉ－２］で表される化合物を、製造方法３の工程３－２と同様な条件を用いて反応させることにより製造することができる。 (Step 8-2)
The compound represented by the general formula [I-16] is produced by reacting the compound represented by the general formula [I-2] under the same conditions as in step 3-2 of the production method 3. can do.
　（工程８－３）
　さらに、一般式［Ｉ－１７］で表される化合物は、一般式［Ｉ－２］で表される化合物を、製造方法３の工程３－３と同様な条件を用いて反応させることにより製造することができる。 (Step 8-3)
Further, the compound represented by the general formula [I-17] is produced by reacting the compound represented by the general formula [I-2] under the same conditions as in Step 3-3 of Production Method 3. can do.
　＜製造方法９＞
　本発明の化合物のうち、一般式［Ｉ－１］で表される化合物は、例えば一般式［Ｉ－２］で表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Production method 9>
Among the compounds of the present invention, the compound represented by the general formula [I-1] can be produced, for example, using a compound represented by the general formula [I-2] according to a method comprising the following reaction formula. Can be.
Figure JPOXMLDOC01-appb-C000085
Figure JPOXMLDOC01-appb-C000085
　（式中、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒａ及びｎは前記と同じ意味を示す。）
　即ち、一般式［Ｉ－１］で表される化合物は、一般式［Ｉ－２］で表される化合物と適当な親電子試薬とを、適当な溶媒の存在下又は非存在下、適当な塩基の存在下又は非存在下、適当な酸の存在下又は非存在下、適当な脱水縮合剤の存在下又は非存在下において反応させることにより製造することができる。
　本反応で使用する親電子試薬の使用量は、化合物［Ｉ－２］１モルに対して、１～溶媒量相当の範囲から適宜選択すればよく、好ましくは１～１５０モルである。
　本反応で塩基を使用する場合、使用できる塩基は、例えば、水酸化ナトリウム、水酸化カリウム、水酸化リチウム等のアルカリ金属の水酸化物類、水酸化カルシウム、水酸化マグネシウム等のアルカリ土類金属の水酸化物類、炭酸ナトリウム、炭酸カリウム等のアルカリ金属の炭酸塩類、炭酸水素ナトリウム、炭酸水素カリウム等のアルカリ金属の重炭酸塩類等の無機塩基類、水素化ナトリウム、水素化カリウム等の金属水素化物類、ナトリウムメトキシド、ナトリウムエトキシド、カリウムｔｅｒｔ－ブトキシド等のアルコールの金属塩類又はトリエチルアミン、Ｎ，Ｎ－ジメチルアニリン、ピリジン、４－Ｎ，Ｎ－ジメチルアミノピリジン、１，８－ジアザビシクロ［５，４，０］－７－ウンデセン等の有機塩基類等が挙げられる。尚、塩基を使用する場合、塩基の使用量は、化合物［Ｉ－２］１モルに対して０．０１～５モルの範囲から適宜選択すればよく、好ましくは０．１～３．０モルである。
　本反応で酸を使用する場合、使用できる酸は、ルイス酸であって、例えば、メタンスルホン酸又はｐ－トルエンスルホン酸等のスルホン酸類、塩酸、臭化水素酸又は硫酸等の鉱酸類、酢酸又はトリフルオロ酢酸等のカルボン酸類等が挙げられる。尚、酸の使用量は、化合物［Ｉ－２］１モルに対して０．００１～５モルの範囲から適宜選択すればよく、好ましくは０．０１～２．０モルである。
　本反応で脱水縮合剤を使用する場合、使用できる脱水縮合剤としては、例えば、Ｎ，Ｎ’－ジシクロヘキシルカルボジイミド、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド、Ｏ－（ベンゾ卜リアゾール－１－イル）－Ｎ，Ｎ，Ｎ’，Ｎ’－テ卜ラメチルウロニウムヘキサフルオロホスファー卜、４－（４，６－ジメトキシ－１，３，５－卜リアジン－２－イル）－４－メチルモルホリニウムクロリド、１－ヒドロキシベンゾ卜リアゾール又はこれらの混合物等が挙げられる。尚、脱水縮合剤の使用量は、化合物［Ｉ－２］１モルに対して各々１～３モルの範囲から適宜選択すればよく、好ましくは各々１．０～１．２モルである。
　本反応で使用できる溶媒としては、例えば、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、メタノール、エタノール、２－プロパノール等のアルコール類、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［Ｉ－２］１モルに対して０．１～１００リットルであり、好ましくは０．３～２０リットルである。
　本反応の反応温度は、－２０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは０℃～１５０℃の範囲で行うのがよい。
　本反応の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１５分～２４時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［Ｉ－１］を単離することができる。単離した化合物［Ｉ－１］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (In the formula, R 3 , R 4 , R 5 , R 6 , Ra and n have the same meaning as described above.)
That is, the compound represented by the general formula [I-1] is prepared by combining the compound represented by the general formula [I-2] with a suitable electrophilic reagent in the presence or absence of a suitable solvent. It can be produced by reacting in the presence or absence of a base, in the presence or absence of a suitable acid, in the presence or absence of a suitable dehydrating condensing agent.
The amount of the electrophilic reagent used in this reaction may be appropriately selected from the range of 1 to the amount of the solvent, and preferably 1 to 150 mol, per 1 mol of compound [I-2].
When a base is used in this reaction, usable bases include, for example, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, and alkaline earth metals such as calcium hydroxide and magnesium hydroxide. Hydroxides, alkali metal carbonates such as sodium carbonate and potassium carbonate, inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, and metals such as sodium hydride and potassium hydride Metal salts of alcohols such as hydrides, sodium methoxide, sodium ethoxide, potassium tert-butoxide or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [ Organic bases such as [5,4,0] -7-undecene. When a base is used, the amount of the base used may be appropriately selected from the range of 0.01 to 5 mol, and preferably 0.1 to 3.0 mol, per 1 mol of compound [I-2]. It is.
When an acid is used in this reaction, the acid that can be used is a Lewis acid, for example, sulfonic acids such as methanesulfonic acid or p-toluenesulfonic acid, mineral acids such as hydrochloric acid, hydrobromic acid or sulfuric acid, and acetic acid. Or carboxylic acids such as trifluoroacetic acid. The amount of the acid used may be appropriately selected from the range of 0.001 to 5 mol per 1 mol of the compound [I-2], and is preferably 0.01 to 2.0 mol.
When a dehydration condensing agent is used in this reaction, examples of the dehydration condensing agent that can be used include N, N′-dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1-ethyl- 3- (3-dimethylaminopropyl) carbodiimide, O- (benzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate, 4- (4 Examples thereof include 6-dimethoxy-1,3,5-triazin-2-yl) -4-methylmorpholinium chloride, 1-hydroxybenzotriazole, and a mixture thereof. The amount of the dehydrating condensing agent to be used may be appropriately selected from the range of 1 to 3 mol per 1 mol of compound [I-2], and is preferably 1.0 to 1.2 mol, respectively.
Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like Aprotic polar solvents, alcohols such as methanol, ethanol, 2-propanol, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and aliphatic carbons such as pentane, hexane, cyclohexane, heptane Hydrogen compound or a mixture solvent thereof. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-20 liters, per 1 mol of compound [I-2].
The reaction temperature of this reaction may be selected from an arbitrary temperature range from −20 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 150 ° C.
The reaction time of this reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 15 minutes to 24 hours.
After completion of the reaction, compound [I-1] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., if necessary.
　＜製造方法１０＞
　本発明の化合物のうち、一般式［Ｉ－１］で表される化合物は、例えば一般式［Ｉ－１８］で表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Production method 10>
Among the compounds of the present invention, the compound represented by the general formula [I-1] can be produced, for example, using a compound represented by the general formula [I-18] according to a method comprising the following reaction formula. Can be.
Figure JPOXMLDOC01-appb-C000086
 　（式中、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒａ及びｎは前記と同じ意味を示し、Ｌ５は水素原子、ハロゲン原子、メチルチオ基、メチルスルフィニル基、メチルスルホニル基又はｐ－トルエンスルホニル基等を示す。）
　即ち、一般式［Ｉ－１］で表される本発明の化合物は、一般式［Ｉ－１８］で表される化合物と化合物［ＩＶ－１５］とを、適当な塩基存在下又は非存在下、適当な溶媒中において反応させることにより製造することができる。
　本反応で使用する化合物［ＩＶ－１５］の使用量は、化合物［Ｉ－１８］１モルに対して１～溶媒量相当の範囲から適宜選択すればよく、好ましくは１．０～１０．０モルである。
　本反応で塩基を使用する場合、使用できる塩基は、例えば、水酸化ナトリウム、水酸化カリウム、水酸化リチウム等のアルカリ金属の水酸化物類、水酸化カルシウム、水酸化マグネシウム等のアルカリ土類金属の水酸化物類、炭酸ナトリウム、炭酸カリウム等のアルカリ金属の炭酸塩類、炭酸水素ナトリウム、炭酸水素カリウム等のアルカリ金属の重炭酸塩類等の無機塩基類、水素化ナトリウム、水素化カリウム等の金属水素化物類、ナトリウムメトキシド、ナトリウムエトキシド、カリウムｔｅｒｔ－ブトキシド等のアルコールの金属塩類又はトリエチルアミン、Ｎ，Ｎ－ジメチルアニリン、ピリジン、４－Ｎ，Ｎ－ジメチルアミノピリジン、１，８－ジアザビシクロ［５，４，０］－７－ウンデセン等の有機塩基類等が挙げられる。尚、塩基の使用量は、化合物［Ｉ－１８］１モルに対して１～１０モルの範囲から適宜選択すればよく、好ましくは１．０～３．０モルである。
　本反応で使用できる溶媒としては、例えば、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、メタノール、エタノール、２－プロパノール等のアルコール類、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類、アセトン、メチルエチルケトン、シクロヘキサノン等のケトン類、水又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［Ｉ－１８］１モルに対して０．１～１００リットルであり、好ましくは０．３～２０リットルである。
　本反応の反応温度は、－２０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは－１０℃～１５０℃の範囲で行うのがよい。
　本反応の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１５分～２０時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［Ｉ－１］を単離することができる。単離した化合物［Ｉ－１］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。
Figure JPOXMLDOC01-appb-C000086
 (Wherein, R 3 , R 4 , R 5 , R 6 , R a and n have the same meanings as described above, and L 5 is a hydrogen atom, a halogen atom, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, or a p- Shows a toluenesulfonyl group, etc.)
That is, the compound of the present invention represented by the general formula [I-1] can be prepared by converting the compound represented by the general formula [I-18] and the compound [IV-15] in the presence or absence of a suitable base. In a suitable solvent.
The amount of compound [IV-15] used in this reaction may be appropriately selected from the range of 1 to the amount of solvent relative to 1 mol of compound [I-18], and is preferably 1.0 to 10.0. Is a mole.
When a base is used in this reaction, usable bases include, for example, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, and alkaline earth metals such as calcium hydroxide and magnesium hydroxide. Hydroxides, alkali metal carbonates such as sodium carbonate and potassium carbonate, inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, and metals such as sodium hydride and potassium hydride Metal salts of alcohols such as hydrides, sodium methoxide, sodium ethoxide, potassium tert-butoxide or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [ Organic bases such as [5,4,0] -7-undecene. The amount of the base to be used may be appropriately selected from the range of 1 to 10 mol per 1 mol of compound [I-18], and is preferably 1.0 to 3.0 mol.
Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like Aprotic polar solvents, alcohols such as methanol, ethanol, 2-propanol, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and aliphatic carbons such as pentane, hexane, cyclohexane, heptane Hydrogen include acetone, methyl ethyl ketone, ketones such as cyclohexanone, water, or a mixed solvent thereof. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-20 liters, per 1 mol of compound [I-18].
The reaction temperature of this reaction may be selected from an arbitrary temperature range from −20 ° C. to the reflux temperature in the reaction system, and is preferably from −10 ° C. to 150 ° C.
The reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 15 minutes to 20 hours.
After completion of the reaction, compound [I-1] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., if necessary.
＜製造方法１１＞
　本発明の化合物のうち、一般式［Ｉ－１］で表される化合物は、例えば一般式［ＩＶ－１６］で表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Production method 11>
Among the compounds of the present invention, the compound represented by the general formula [I-1] can be produced, for example, using a compound represented by the general formula [IV-16] according to a method comprising the following reaction formula. Can be.
Figure JPOXMLDOC01-appb-C000087
Figure JPOXMLDOC01-appb-C000087
　（式中、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒａ及びｎは前記と同じ意味を示し、Ｌ６はハロゲン原子、メタンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基、ノナフルオロブタンスルホニルオキシ基、ベンゼンスルホニルオキシ基、ｐ－トルエンスルホニルオキシ基、ジメチルスルファモイルオキシ基、ジヒドロキシボリル基（Ｂ（ＯＨ）２）又はピナコラートボラン－２－イル基等を示す。）
　即ち、一般式［Ｉ－１］で表される化合物は、化合物［ＩＶ－１６］と化合物［ＩＶ－１７］とを、国際公開特許公報ＷＯ２００６／０４３６３５号又は欧州特許公報ＥＰ３００２２７９号に記載されている方法又はその方法に準じて、芳香族求核置換反応又はクロスカップリング反応させることにより製造することができる。 (Wherein, R 3 , R 4 , R 5 , R 6 , Ra and n have the same meaning as described above, and L 6 represents a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a nonafluorobutanesulfonyloxy A benzenesulfonyloxy group, a p-toluenesulfonyloxy group, a dimethylsulfamoyloxy group, a dihydroxyboryl group (B (OH) 2 ), or a pinacolatoboran-2-yl group.
That is, the compound represented by the general formula [I-1] is obtained by converting the compound [IV-16] and the compound [IV-17] into International Patent Publication WO2006 / 043635 or European Patent Publication EP30022279. Can be produced by performing an aromatic nucleophilic substitution reaction or a cross-coupling reaction according to the method described above or according to the method.
＜製造方法１２＞
　本発明の化合物のうち、一般式［ＩＩ－２］で表される化合物は、例えば一般式［ＩＩＩ－４］で表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Production method 12>
Among the compounds of the present invention, the compound represented by the general formula [II-2] can be produced, for example, using a compound represented by the general formula [III-4] according to a method comprising the following reaction formula. Can be.
Figure JPOXMLDOC01-appb-C000088
Figure JPOXMLDOC01-appb-C000088
　（式中、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｚ、ｐ１及びｎは前記と同じ意味を示し、Ｘはハロゲン原子を示し、ＲｄはＣ１～Ｃ６アルキル基、フェニル基又は無置換若しくは（Ｚ）ｐ１により置換されたフェニルＣ１～Ｃ６アルキル基等を示す。）
　即ち、一般式［ＩＩ－２］で表される化合物は、一般式［ＩＩＩ－５］で表される化合物を適当な触媒の存在下又は非存在下、適当な溶媒中においてシアノ化し、一般式［ＩＩＩ－６］で表される化合物とした後、適当な酸又は塩基の存在下、適当な溶媒中において加水分解反応させることにより製造することができる。 (Wherein, R 3 , R 4 , R 5 , R 6 , Z, p 1 and n have the same meanings as above, X represents a halogen atom, R d represents a C 1 -C 6 alkyl group, a phenyl group Or a phenyl C 1 -C 6 alkyl group which is unsubstituted or substituted by (Z) p 1 .
That is, the compound represented by the general formula [II-2] can be obtained by cyanating the compound represented by the general formula [III-5] in a suitable solvent in the presence or absence of a suitable catalyst, in a suitable solvent. It can be produced by subjecting the compound represented by [III-6] to a hydrolysis reaction in a suitable solvent in the presence of a suitable acid or base.
（工程１２－１）
　本工程で使用するシアン化合物としては、例えば、シアン化ナトリウム、シアン化カリウム、シアン化アンモニウム、シアン化亜鉛、シアン化銅、又はこれらの混合物を挙げることができる。尚、シアン化合物の使用量は、化合物［ＩＩＩ－５］１モルに対して通常１～１００モルの範囲から適宜選択すればよく、好ましくは１．０～５．０モルである。
　本工程で使用する触媒としては、テトラキス（トリフェニルホスフィン）パラジウムを挙げることができる。尚、触媒の使用量は、化合物［ＩＩＩ－５］１モルに対して通常０．００１～０．５モルの範囲から適宜選択すればよく、好ましくは０．０１～０．１モルである。
　本工程で使用できる溶媒としては、例えばジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、メタノール、エタノール、２－プロパノール等のアルコール類、酢酸エチル等のエステル類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類、ピリジン、ピコリン等のピリジン類、水、又はこれらの混合溶媒等を挙げることができる。尚、溶媒の使用量は、化合物［ＩＩＩ－５］１モルに対して０．１～５００リットルであり、好ましくは０．３～５０リットルである。
　本工程の反応温度は、通常－３０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは０℃～１５０℃の範囲で行うのがよい。
　本工程の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１０分～７２時間である。
　反応終了後は、反応混合物を水に注加し、析出した固体を濾取するまたは有機溶媒にて抽出してから濃縮する等の操作を行うことにより、化合物［ＩＩＩ－６］を単離することができる。単離した化合物［ＩＩＩ－６］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 12-1)
Examples of the cyan compound used in this step include sodium cyanide, potassium cyanide, ammonium cyanide, zinc cyanide, copper cyanide, and mixtures thereof. The amount of the cyan compound to be used may be appropriately selected usually from the range of 1 to 100 mol per 1 mol of the compound [III-5], and is preferably 1.0 to 5.0 mol.
Examples of the catalyst used in this step include tetrakis (triphenylphosphine) palladium. The amount of the catalyst to be used may be appropriately selected usually from the range of 0.001 to 0.5 mol per 1 mol of the compound [III-5], and is preferably from 0.01 to 0.1 mol.
Examples of the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; and dichloromethane. , Chloroform, halogenated hydrocarbons such as 1,2-dichloroethane, etc., nitriles such as acetonitrile, propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , Sulfolane, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol and 2-propanol, esters such as ethyl acetate, pentane, hexane and cyclohexa , Aliphatic hydrocarbons such as heptane, pyridine, pyridine picoline, etc., can be mentioned water, or a mixed solvent thereof, or the like. The amount of the solvent to be used is 0.1 to 500 liter, preferably 0.3 to 50 liter, per 1 mol of compound [III-5].
The reaction temperature in this step may be selected from an arbitrary temperature range from usually −30 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 150 ° C.
The reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually from 10 minutes to 72 hours.
After completion of the reaction, compound [III-6] is isolated by performing operations such as pouring the reaction mixture into water, and collecting the precipitated solid by filtration or extraction with an organic solvent and then concentration. be able to. The isolated compound [III-6] can be further purified, if necessary, by column chromatography, recrystallization and the like.
　（工程１２－２）
　本工程で使用できる酸としては、例えば、塩酸、臭化水素酸又は硫酸等の鉱酸類、酢酸又はトリフルオロ酢酸等のカルボン酸類、メタンスルホン酸又はトリフルオロメタンスルホン酸等のスルホン酸類等を挙げることができる。尚、酸の使用量は、化合物［ＩＩＩ－６］１モルに対して１～溶媒量相当モルの範囲から適宜選択すればよく、好ましくは１．０～１００．０モルである。
　本工程で使用できる塩基としては、例えば、水酸化ナトリウム、水酸化カリウム、水酸化リチウム等のアルカリ金属の水酸化物類、炭酸ナトリウム、炭酸カリウム等のアルカリ金属の炭酸塩類、炭酸水素ナトリウム、炭酸水素カリウム等のアルカリ金属の重炭酸塩類等の無機塩基類等を挙げることができる。尚、塩基の使用量は、化合物［ＩＩＩ－６］１モルに対して０．１～５０モルの範囲から適宜選択すればよく、好ましくは０．５～２０．０モルである。
　本工程で使用できる溶媒としては、例えば、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、メタノール、エタノール、２－プロパノール等のアルコール類、アセトン、メチルエチルケトン、シクロヘキサノン等のケトン類、水、又はこれらの混合溶媒等を挙げることができる。尚、溶媒の使用量は、化合物［ＩＩＩ－６］１モルに対して０．１～５００リットルであり、好ましくは０．３～３０リットルである。
　本工程の反応温度は、通常－３０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは０℃～１５０℃の範囲で行うのがよい。
　本工程の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１０分～７２時間である。
　反応終了後は、反応混合物を水に注加し中和した後、析出した固体を濾取する又は有機溶媒にて抽出してから濃縮する等の操作を行うことにより、化合物［ＩＩ－２］を単離することができる。単離した化合物［ＩＩ－２］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 12-2)
Examples of the acid that can be used in this step include mineral acids such as hydrochloric acid, hydrobromic acid and sulfuric acid, carboxylic acids such as acetic acid and trifluoroacetic acid, and sulfonic acids such as methanesulfonic acid and trifluoromethanesulfonic acid. Can be. The amount of the acid to be used may be appropriately selected from the range of 1 to the equivalent of the amount of the solvent per 1 mol of the compound [III-6], and is preferably 1.0 to 100.0 mol.
Examples of the base that can be used in this step include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, and lithium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydrogen carbonate; And inorganic bases such as alkali metal bicarbonates such as potassium hydrogen. The amount of the base used may be appropriately selected from the range of 0.1 to 50 mol per 1 mol of compound [III-6], and is preferably 0.5 to 20.0 mol.
Examples of the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like Examples include aprotic polar solvents, alcohols such as methanol, ethanol and 2-propanol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, water, and mixed solvents thereof. The amount of the solvent to be used is 0.1-500 liter, preferably 0.3-30 liter, per 1 mol of compound [III-6].
The reaction temperature in this step may be selected from an arbitrary temperature range from usually −30 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 150 ° C.
The reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually from 10 minutes to 72 hours.
After completion of the reaction, the reaction mixture is poured into water for neutralization, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to obtain the compound [II-2]. Can be isolated. The isolated compound [II-2] can be further purified, if necessary, by column chromatography, recrystallization and the like.
　（工程１２－３）
　尚、一般式［ＩＩ－２］で表される化合物は、Ｊ．Ｏｒｇａｎｏｍｅｔａｌ．Ｃｈｅｍ．，３５８巻，５６３頁～５６５頁（１９８８年）に記載されている方法又はその方法に準じて、パラジウム等の遷移金属触媒を用いるＣＯ挿入反応させることにより製造することができる。
　また、一般式［ＩＩ－２］で表される化合物は、Ｃｈｅｍ．Ｒｅｖ．，９０巻，８７９頁～９３３頁（１９９０年）に記載されている方法又はその方法に準じて、リチオ化した後、炭酸ガスと反応させることにより製造することができる。 (Step 12-3)
The compound represented by the general formula [II-2] is described in J. Am. Organometal. Chem. 358, pp. 563 to 565 (1988) or by a CO insertion reaction using a transition metal catalyst such as palladium according to the method.
The compound represented by the general formula [II-2] is described in Chem. Rev .. 90, pages 879 to 933 (1990), or lithiated and then reacted with carbon dioxide gas according to the method.
　（工程１２－４）
　さらに、一般式［ＩＩ－２］で表される化合物は、Ｊ．Ｏｒｇ．Ｃｈｅｍ．，３９巻，３３１８頁～３３２６頁（１９７４年）に記載されている方法又はその方法に準じて、パラジウム等の遷移金属触媒を用いるＣＯ挿入反応させることにより、一般式［ＩＩ－１］で表される化合物とした後、適当な酸又は塩基の存在下、適当な溶媒中において加水分解反応させることにより製造することができる。 (Step 12-4)
Further, the compound represented by the general formula [II-2] is described in J. Am. Org. Chem. 39, pp. 3318-3326 (1974), or by a CO insertion reaction using a transition metal catalyst such as palladium according to the method described above, to obtain a compound represented by the general formula [II-1]. And then subjecting the compound to a hydrolysis reaction in a suitable solvent in the presence of a suitable acid or base.
　（工程１２－５）
　本工程で使用できる酸、塩基、溶媒、反応温度及び反応時間は、工程１２－２と同様である。
　反応終了後は、反応混合物を水に注加し中和した後、析出した固体を濾取する又は有機溶媒にて抽出してから濃縮する等の操作を行うことにより、化合物［ＩＩ－２］を単離することができる。単離した化合物［ＩＩ－２］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 12-5)
The acid, base, solvent, reaction temperature and reaction time that can be used in this step are the same as in Step 12-2.
After completion of the reaction, the reaction mixture is poured into water for neutralization, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to obtain the compound [II-2]. Can be isolated. The isolated compound [II-2] can be further purified, if necessary, by column chromatography, recrystallization and the like.
＜製造方法１３＞
　本発明の化合物のうち、一般式［Ｉ－１９］で表される化合物は、例えば一般式［ＩＩ－２］で表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Production method 13>
Among the compounds of the present invention, the compound represented by the general formula [I-19] can be produced, for example, using a compound represented by the general formula [II-2] according to a method comprising the following reaction formula. Can be.
Figure JPOXMLDOC01-appb-C000089
Figure JPOXMLDOC01-appb-C000089
　（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒｂ及びｎは前記と同じ意味を示し、Ｌ７はハロゲン原子、－ＯＣ（＝Ｏ）ＯＲｂ、メタンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基、ベンゼンスルホニルオキシ基又はｐ－トルエンスルホニルオキシ基を示す。） (Wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R b and n have the same meaning as described above, L 7 is a halogen atom, —OC (＝ O) OR b , methane Which represents a sulfonyloxy group, a trifluoromethanesulfonyloxy group, a benzenesulfonyloxy group or a p-toluenesulfonyloxy group.)
　（工程１３－１）
　即ち、一般式［Ｉ－１９］で表される化合物は、一般式［ＩＩ－２］で表される化合物と化合物［ＩＶ－１８］とを、適当な脱水縮合剤及び適当な塩基の存在下又は非存在下、適当な溶媒中において反応させることにより製造することができる。
　本工程で使用する化合物［ＩＶ－１８］の使用量は、化合物［ＩＩ－２］１モルに対して１～１０モルの範囲から適宜選択すればよく、好ましくは１．０～５．０モルである。
　本工程で使用できる脱水縮合剤は、例えば、Ｎ，Ｎ’－ジシクロヘキシルカルボジイミド、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド、Ｏ－（ベンゾ卜リアゾール－１－イル）－Ｎ，Ｎ，Ｎ’，Ｎ’－テ卜ラメチルウロニウムヘキサフルオロホスファー卜、４－（４，６－ジメトキシ－１，３，５－卜リアジン－２－イル）－４－メチルモルホリニウムクロリド、１－ヒドロキシベンゾ卜リアゾール又はこれらの混合物等が挙げられる。尚、脱水縮合剤の使用量は化合物［ＩＩ－２］１モルに対して各々１～５モルの範囲から適宜選択すればよく、好ましくは各々１．０～３．０モルである。
　本工程で塩基を使用する場合、使用できる塩基は、例えば、卜リエチルアミン、４－メチルモルホリン、ジイソプロピルエチルアミン、１，８－ジアザビシクロ［５．４．０］－７－ウンデセン、ピリジン、４－Ｎ，Ｎ－ジメチルアミノピリジン、２，６－ルチジン等の有機塩基類等が挙げられる。尚、塩基の使用量は、化合物［ＩＩ－２］１モルに対して０．１～５モルの範囲から適宜選択すればよく、好ましくは０．１～３．０モルである。
　本工程で使用できる溶媒としては、例えば、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類、酢酸エチル等のエステル類、アセ卜ニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類又はこれらの混合溶媒等を挙げることができる。尚、溶媒の使用量は、化合物［ＩＩ－２］１モルに対して０．１～１００リットルであり、好ましくは０．３～５０リットルである。
　本工程は、必要に応じて触媒の存在下で行うことができ、触媒は、４－Ｎ，Ｎ－ジメチルアミノピリジン等から適宜選択できる。尚、用いられる触媒の使用量は、化合物［ＩＩ－２］１モルに対して０．００１～１モルの範囲から適宜選択すればよく、好ましくは０．０１～０．１モルである。
　本工程の反応温度は、－２０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは０℃～８０℃の範囲で行うのがよい。
　本工程の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１分～１００時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［Ｉ－１９］を単離することができる。単離した化合物［Ｉ－１９］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 13-1)
That is, the compound represented by the general formula [I-19] can be obtained by converting the compound represented by the general formula [II-2] and the compound [IV-18] in the presence of a suitable dehydrating condensing agent and a suitable base. Alternatively, it can be produced by reacting in a suitable solvent in the absence.
The amount of compound [IV-18] used in this step may be appropriately selected from the range of 1 to 10 mol per 1 mol of compound [II-2], and is preferably 1.0 to 5.0 mol. It is.
The dehydrating condensing agent that can be used in this step includes, for example, N, N′-dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1-ethyl-3- (3-dimethylaminopropyl) Carbodiimide, O- (benzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium hexafluorophosphate, 4- (4,6-dimethoxy-1,3,5 -Triazin-2-yl) -4-methylmorpholinium chloride, 1-hydroxybenzotriazole or a mixture thereof. The amount of the dehydrating condensing agent may be appropriately selected from the range of 1 to 5 moles per 1 mole of the compound [II-2], and is preferably 1.0 to 3.0 moles.
When a base is used in this step, usable bases include, for example, triethylamine, 4-methylmorpholine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] -7-undecene, pyridine, 4-N , N-dimethylaminopyridine, and organic bases such as 2,6-lutidine. The amount of the base used may be appropriately selected from the range of 0.1 to 5 mol per 1 mol of compound [II-2], and is preferably 0.1 to 3.0 mol.
Examples of the solvent that can be used in this step include halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; esters such as ethyl acetate; Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone Aprotic polar solvents, such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and the like; and mixed solvents thereof. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-50 liters, per 1 mol of compound [II-2].
This step can be performed in the presence of a catalyst, if necessary, and the catalyst can be appropriately selected from 4-N, N-dimethylaminopyridine and the like. The amount of the catalyst used may be appropriately selected from the range of 0.001 to 1 mol per 1 mol of the compound [II-2], and is preferably 0.01 to 0.1 mol.
The reaction temperature in this step may be selected from an arbitrary temperature range from −20 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 80 ° C.
The reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 1 minute to 100 hours.
After completion of the reaction, compound [I-19] can be isolated by performing an operation such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-19] can be further purified, if necessary, by column chromatography, recrystallization and the like.
　（工程１３－２）
　また、一般式［Ｉ－１９］で表される本発明の化合物は、一般式［ＩＩ－２］で表される化合物を、適当な触媒の存在下又は非存在下、適当な溶媒中において酸ハロゲン化物又は混合酸無水物等の活性誘導体である化合物［ＩＩ－３］に変換させた後、化合物［ＩＶ－１８］と、適当な塩基の存在下、適当な溶媒中において反応させることにより製造することもできる。
　化合物［ＩＩ－２］を酸ハロゲン化物に変換するためには、塩化チオニル又は塩化オキサリル等を用いることができる。その他の活性誘導体に変換させる試薬として、クロロ炭酸イソブチル、メタンスルホニルクロリド、卜リフルオロメタンスルホニルクロリド、ｐ－卜ルエンスルホニルクロリド等を使用することができる。尚、活性誘導体に変換させる試薬の使用量は、化合物［ＩＩ－２］１モルに対して０．５～５モルの範囲から適宜選択すればよく、好ましくは０．５～２．２モルである。
　本工程で触媒を使用する場合、使用できる触媒は、例えば、Ｎ，Ｎ－ジメチルホルムアミド等を挙げることができる。尚、触媒の使用量は、化合物［ＩＩ－２］１モルに対して０．０１～１モルの範囲から適宜選択すればよく、好ましくは０．０１～０．３モルである。
　本工程で使用できる溶媒としては、例えば、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類、アセ卜ニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類又はこれらの混合溶媒等を挙げることができる。尚、溶媒の使用量は、化合物［ＩＩ－２］１モルに対して０．１～１００リットルであり、好ましくは０．３～１０リットルである。
　本工程の反応温度は、－２０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは０℃～８０℃の範囲で行うのがよい。
　本工程の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１分～４８時間である。
　反応終了後は、濃縮する等の操作を行うことにより、化合物［ＩＩ－３］を単離することができる。 (Step 13-2)
Further, the compound of the present invention represented by the general formula [I-19] can be prepared by converting the compound represented by the general formula [II-2] in an appropriate solvent in the presence or absence of an appropriate catalyst in an appropriate solvent. The compound is converted to a compound [II-3] which is an active derivative such as a halide or a mixed acid anhydride, and then reacted with a compound [IV-18] in a suitable solvent in the presence of a suitable base. You can also.
In order to convert the compound [II-2] to an acid halide, thionyl chloride or oxalyl chloride can be used. As a reagent to be converted into another active derivative, isobutyl chlorocarbonate, methanesulfonyl chloride, trifluoromethanesulfonyl chloride, p-toluenesulfonyl chloride and the like can be used. The amount of the reagent to be converted into the active derivative may be appropriately selected from the range of 0.5 to 5 mol per 1 mol of the compound [II-2], and is preferably 0.5 to 2.2 mol. is there.
When a catalyst is used in this step, usable catalysts include, for example, N, N-dimethylformamide and the like. The amount of the catalyst to be used may be appropriately selected from the range of 0.01 to 1 mol per 1 mol of the compound [II-2], and is preferably 0.01 to 0.3 mol.
Examples of the solvent that can be used in this step include halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, pentane, hexane, cyclohexane and heptane. Such as aliphatic hydrocarbons such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3 Aprotic polar solvents such as -dimethyl-2-imidazolidinone; ethers such as diethyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; and mixed solvents thereof. it can. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [II-2].
The reaction temperature in this step may be selected from an arbitrary temperature range from −20 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 80 ° C.
The reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually from 1 minute to 48 hours.
After completion of the reaction, compound [II-3] can be isolated by performing an operation such as concentration.
　（工程１３－３）
　得られた化合物［ＩＩ－３］を含む反応溶液に、通常、化合物［ＩＶ－１８］を適当な塩基存在下、適当な溶媒中において反応させることにより、化合物［Ｉ－１９］を製造することができる。
　本工程で使用する化合物［ＩＶ－１８］の使用量は、化合物［ＩＩ－２］１モルに対して１～３モルの範囲から適宜選択すればよく、好ましくは１．０～２．５モルである。
　本工程で使用できる塩基は、例えば、水酸化ナトリウム、水酸化カリウム、水酸化リチウム等のアルカリ金属の水酸化物類、炭酸ナトリウム、炭酸カリウム等のアルカリ金属の炭酸塩類、炭酸水素ナトリウム、炭酸水素カリウム等のアルカリ金属の重炭酸塩類等の無機塩基類、水素化ナトリウム、水素化カリウム等の金属水素化物類又はトリエチルアミン、Ｎ，Ｎ－ジメチルアニリン、ピリジン、４－Ｎ，Ｎ－ジメチルアミノピリジン、１，８－ジアザビシクロ［５，４，０］－７－ウンデセン等の有機塩基類等が挙げられる。尚、塩基の使用量は、化合物［ＩＩ－２］１モルに対して１～５モルの範囲から適宜選択すればよく、好ましくは１．０～２．５モルである。
　本工程で使用できる溶媒としては、例えば、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類、アセ卜ニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、水又はこれらの混合溶媒等を挙げることができる。尚、溶媒の使用量は、化合物［ＩＩ－２］１モルに対して０．１～１００リットルであり、好ましくは０．３～１０リットルである。
　本工程の反応温度は、－２０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは０℃～８０℃の範囲で行うのがよい。
　本工程の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１分～４８時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［Ｉ－１９］を単離することができる。単離した化合物［Ｉ－１９］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 13-3)
Production of compound [I-19] by reacting compound [IV-18] with the obtained reaction solution containing compound [II-3] in the presence of a suitable base and in a suitable solvent. Can be.
The amount of compound [IV-18] used in this step may be appropriately selected from the range of 1 to 3 mol per 1 mol of compound [II-2], and is preferably 1.0 to 2.5 mol. It is.
Bases that can be used in this step include, for example, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, and lithium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, sodium hydrogen carbonate, and hydrogen carbonate. Inorganic bases such as bicarbonates of alkali metals such as potassium, metal hydrides such as sodium hydride and potassium hydride or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine; Organic bases such as 1,8-diazabicyclo [5,4,0] -7-undecene are exemplified. The amount of the base used may be appropriately selected from the range of 1 to 5 mol per 1 mol of the compound [II-2], and is preferably 1.0 to 2.5 mol.
Examples of the solvent that can be used in this step include halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene, pentane, hexane, cyclohexane, and heptane. Such as aliphatic hydrocarbons such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3 Aprotic polar solvents such as -dimethyl-2-imidazolidinone, ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; water; and mixed solvents thereof. be able to. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [II-2].
The reaction temperature in this step may be selected from an arbitrary temperature range from −20 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 80 ° C.
The reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually from 1 minute to 48 hours.
After completion of the reaction, compound [I-19] can be isolated by performing an operation such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-19] can be further purified, if necessary, by column chromatography, recrystallization and the like.
　＜製造方法１４＞
　本発明の化合物のうち、一般式［Ｉ］で表される化合物は、例えば一般式［Ｉ－２０］で表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Production method 14>
Among the compounds of the present invention, the compound represented by the general formula [I] can be produced, for example, using a compound represented by the general formula [I-20] according to a method comprising the following reaction formula. .
Figure JPOXMLDOC01-appb-C000090
Figure JPOXMLDOC01-appb-C000090
　（式中、Ａ、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６及びｎは前記と同じ意味を示し、Ｌ８はハロゲン原子、メタンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基、ノナフルオロブタンスルホニルオキシ基、ベンゼンスルホニルオキシ基又はｐ－トルエンスルホニルオキシ基等を示す。）
　即ち、一般式［Ｉ］で表される本発明の化合物は、一般式［Ｉ－２０］で表される化合物と化合物［ＩＶ－１９］とを適当な塩基存在下又は非存在下、適当な溶媒中において反応させることにより製造することができる。
　本反応で使用する化合物［ＩＶ－１９］の使用量は、化合物［Ｉ－２０］１モルに対して１～１００モルの範囲から適宜選択すればよく、好ましくは１．０～１０．０モルである。
　本反応で塩基を使用する場合、使用できる塩基は、例えば、水酸化ナトリウム、水酸化カリウム、水酸化リチウム等のアルカリ金属の水酸化物類、水酸化カルシウム、水酸化マグネシウム等のアルカリ土類金属の水酸化物類、炭酸ナトリウム、炭酸カリウム等のアルカリ金属の炭酸塩類、炭酸水素ナトリウム、炭酸水素カリウム等のアルカリ金属の重炭酸塩類等の無機塩基類、水素化ナトリウム、水素化カリウム等の金属水素化物類、ナトリウムメトキシド、ナトリウムエトキシド、カリウムｔｅｒｔ－ブトキシド等のアルコールの金属塩類又はトリエチルアミン、Ｎ，Ｎ－ジメチルアニリン、ピリジン、４－Ｎ，Ｎ－ジメチルアミノピリジン、１，８－ジアザビシクロ［５，４，０］－７－ウンデセン等の有機塩基類等が挙げられる。尚、塩基の使用量は、化合物［Ｉ－２０］１モルに対して１～１０モルの範囲から適宜選択すればよく、好ましくは１．０～５．０モルである。
　本反応で使用できる溶媒としては、例えば、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、酢酸エチル等のエステル類、アセトニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、メタノール、エタノール、２－プロパノール等のアルコール類、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類、アセトン、メチルエチルケトン、シクロヘキサノン等のケトン類又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［Ｉ－２０］１モルに対して０．１～１００リットルであり、好ましくは０．３～２０リットルである。
　本反応の反応温度は、－２０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは－１０℃～８０℃の範囲で行うのがよい。
　本反応の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１５分～４８時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［Ｉ］を単離することができる。単離した化合物［Ｉ］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Wherein, A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n have the same meaning as described above, and L 8 represents a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, And a nonafluorobutanesulfonyloxy group, a benzenesulfonyloxy group, a p-toluenesulfonyloxy group, and the like.)
That is, the compound of the present invention represented by the general formula [I] can be obtained by converting the compound represented by the general formula [I-20] and the compound [IV-19] in the presence or absence of a suitable base. It can be produced by reacting in a solvent.
The amount of compound [IV-19] to be used in this reaction may be appropriately selected from the range of 1 to 100 mol per 1 mol of compound [I-20], and is preferably 1.0 to 10.0 mol. It is.
When a base is used in this reaction, usable bases include, for example, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, and alkaline earth metals such as calcium hydroxide and magnesium hydroxide. Hydroxides, alkali metal carbonates such as sodium carbonate and potassium carbonate, inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, and metals such as sodium hydride and potassium hydride Metal salts of alcohols such as hydrides, sodium methoxide, sodium ethoxide, potassium tert-butoxide or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [ Organic bases such as [5,4,0] -7-undecene. The amount of the base to be used may be appropriately selected from the range of 1 to 10 mol per 1 mol of compound [I-20], and is preferably 1.0 to 5.0 mol.
Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Esters such as ethyl acetate, nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl- Aprotic polar solvents such as 2-imidazolidinone, alcohols such as methanol, ethanol and 2-propanol, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, pentane, hexane, cyclohexyl Emissions, aliphatic hydrocarbons such as heptane, ketones such as acetone, methyl ethyl ketone or a mixed solvent thereof, such as cyclohexanone. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-20 liters, per 1 mol of compound [I-20].
The reaction temperature of this reaction may be selected from an arbitrary temperature range from −20 ° C. to the reflux temperature in the reaction system, and is preferably from −10 ° C. to 80 ° C.
The reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 15 minutes to 48 hours.
After completion of the reaction, the compound [I] can be isolated by pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I] can be further purified by column chromatography, recrystallization or the like, if necessary.
　＜製造方法１５＞
　本発明の化合物のうち、一般式［Ｉ－２１］で表される化合物は、例えば一般式［Ｉ－１９］で表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Production method 15>
Among the compounds of the present invention, the compound represented by the general formula [I-21] can be produced, for example, using a compound represented by the general formula [I-19] according to a method comprising the following reaction formula. Can be.
Figure JPOXMLDOC01-appb-C000091
Figure JPOXMLDOC01-appb-C000091
　（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６及びｎは前記と同じ意味を示す。）
　即ち、一般式［Ｉ－２１］で表される化合物は、一般式［Ｉ－１９］で表される化合物と適当なチオカルボニル化剤とを、適当な塩基の存在下又は非存在下、適当な溶媒の存在下又は非存在下において反応させることにより製造することができる。
　本反応で使用するチオカルボニル化剤は、五硫化二リン又はローソン試薬（Ｌａｗｅｓｓｏｎ’ｓ　Ｒｅａｇｅｎｔ、　２，４－ビス（４－メトキシフェニル）－１，３，２，４－ジチアジホスフェタン－２，４－ジスルフィド）等が挙げられる。尚、チオカルボニル化剤の使用量は、化合物［Ｉ－１９］１モルに対して、０．５～１００モルの範囲から適宜選択すればよく、好ましくは０．５～３．０モルである。
　本反応で塩基の添加は必ずしも必要ではないが、塩基を使用する場合、使用できる塩基は、例えば、炭酸ナトリウム、炭酸カリウム等のアルカリ金属の炭酸塩類等の無機塩基類又はトリエチルアミン、Ｎ，Ｎ－ジメチルアニリン、ピリジン、４－Ｎ，Ｎ－ジメチルアミノピリジン、１，８－ジアザビシクロ［５，４，０］－７－ウンデセン等の有機塩基類等が挙げられる。尚、塩基の使用量は、化合物［Ｉ－１９］１モルに対して０．０１～１０モルの範囲から適宜選択すればよく、好ましくは０．１～２．０モルである。
　本反応で使用できる溶媒としては、例えば、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、ジメチルスルホキシド、スルホラン等の非プロトン性極性溶媒類、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［Ｉ－１９］１モルに対して０．１～１００リットルであり、好ましくは０．３～１５リットルである。
　本反応の反応温度は、０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは０℃～１５０℃の範囲で行うのがよい。
　本反応の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１５分～４８時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［Ｉ－１９］を単離することができる。単離した化合物［Ｉ－１９］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n have the same meaning as described above.)
That is, the compound represented by the general formula [I-21] can be prepared by combining the compound represented by the general formula [I-19] with a suitable thiocarbonylating agent in the presence or absence of a suitable base. It can be produced by reacting in the presence or absence of a suitable solvent.
The thiocarbonylating agent used in this reaction is diphosphorus pentasulfide or Lawesson's Reagent (2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane- 2,4-disulfide) and the like. The amount of the thiocarbonylating agent to be used may be appropriately selected from the range of 0.5 to 100 mol, preferably 0.5 to 3.0 mol, per 1 mol of compound [I-19]. .
Addition of a base is not always necessary in this reaction, but when a base is used, examples of the usable base include inorganic bases such as alkali metal carbonates such as sodium carbonate and potassium carbonate, and triethylamine, N, N- Organic bases such as dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, and 1,8-diazabicyclo [5,4,0] -7-undecene are exemplified. The amount of the base to be used may be appropriately selected from the range of 0.01 to 10 mol, and preferably 0.1 to 2.0 mol, per 1 mol of compound [I-19].
Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Aprotic polar solvents such as dimethyl sulfoxide and sulfolane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane, or mixed solvents thereof Is mentioned. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-15 liters, per 1 mol of compound [I-19].
The reaction temperature of this reaction may be selected from an arbitrary temperature range from 0 ° C. to the reflux temperature in the reaction system, and is preferably from 0 ° C. to 150 ° C.
The reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 15 minutes to 48 hours.
After completion of the reaction, compound [I-19] can be isolated by performing an operation such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [I-19] can be further purified, if necessary, by column chromatography, recrystallization and the like.
＜中間体の製造方法１＞
　一般式［ＩＩＩ－３］で表される化合物は、例えば一般式［ＩＩＩ－７］で表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Method 1 for producing intermediate>
The compound represented by the general formula [III-3] can be produced, for example, using a compound represented by the general formula [III-7] according to a method comprising the following reaction formula.
Figure JPOXMLDOC01-appb-C000092
Figure JPOXMLDOC01-appb-C000092
　（式中、Ｒ３、Ｒ４、Ｒａ及びｎは前記と同じ意味を示す。） (In the formula, R 3 , R 4 , R a and n have the same meaning as described above.)
　（工程１’－１）
　即ち、一般式［ＩＩＩ－８］で表される化合物は、実験化学講座第４版（丸善）、第２６巻の「還元一般の項」に準じて、一般式［ＩＩＩ－７］で表されるニトロ化合物を還元することにより製造することができる。
　化合物［ＩＩＩ－７］は、一般的に入手可能な試薬を用いることができ、また、国際公開特許公報ＷＯ２００９／０７８４８１号に記載されている方法又はその方法に準じて製造することもできる。 (Step 1'-1)
That is, the compound represented by the general formula [III-8] is represented by the general formula [III-7] in accordance with “Reduced general term” in Vol. By reducing the nitro compound.
As the compound [III-7], generally available reagents can be used, and the compound [III-7] can also be produced by a method described in International Publication WO2009 / 078481 or a method similar thereto.
　（工程１’－２）
　一般式［ＩＩＩ－３］で表される化合物は、一般式［ＩＩＩ－８］で表される化合物と亜硝酸塩とを、適当な鉱酸の存在下、適当な溶媒中において反応させることによりジアゾニウム塩とした後、これを亜鉛末、亜硫酸ナトリウム、塩化スズ等の金属還元試薬で還元することにより製造することができる。
　本工程で使用できる鉱酸は、塩酸、硫酸等が挙げられる。尚、鉱酸の使用量は、化合物［ＩＩＩ－８］１モルに対して２～１０モルの範囲から適宜選択すればよく、好ましくは２．０～５．０モルである。
　本工程で使用する亜硝酸塩の使用量は、化合物［ＩＩＩ－８］１モルに対して１～５モルの範囲から適宜選択すればよく、好ましくは１．０～１．２モルである。
　本工程で使用できる金属還元試薬の使用量は、化合物［ＩＩＩ－８］１モルに対して１～２０モルの範囲から適宜選択すればよく、好ましくは１．０～５．０モルである。
　本工程で使用できる溶媒としては、例えば、水、塩酸、硫酸、酢酸又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［ＩＩＩ－８］１モルに対して０．１～１００リットルであり、好ましくは０．３～１０リットルである。
　本工程の反応温度は、－２０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは－５℃～２０℃の範囲で行うのがよい。
　本工程の反応時間は、反応温度、反応基質、反応量等により異なるが、通常３０分～５時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［ＩＩＩ－３］を単離することができる。単離した化合物［ＩＩＩ－３］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 1'-2)
The compound represented by the general formula [III-3] is prepared by reacting the compound represented by the general formula [III-8] with a nitrite in a suitable solvent in the presence of a suitable mineral acid. After being converted to a salt, it can be produced by reducing it with a metal reducing reagent such as zinc dust, sodium sulfite, tin chloride or the like.
Mineral acids that can be used in this step include hydrochloric acid, sulfuric acid and the like. The amount of the mineral acid to be used may be appropriately selected from the range of 2 to 10 mol per 1 mol of the compound [III-8], and is preferably 2.0 to 5.0 mol.
The amount of the nitrite used in this step may be appropriately selected from the range of 1 to 5 mol per 1 mol of the compound [III-8], and is preferably 1.0 to 1.2 mol.
The amount of the metal reducing reagent that can be used in this step may be appropriately selected from the range of 1 to 20 mol per 1 mol of compound [III-8], and is preferably 1.0 to 5.0 mol.
Examples of the solvent that can be used in this step include water, hydrochloric acid, sulfuric acid, acetic acid, a mixed solvent thereof, and the like. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-8].
The reaction temperature in this step may be selected from an arbitrary temperature range from −20 ° C. to the reflux temperature in the reaction system, and is preferably from −5 ° C. to 20 ° C.
The reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 30 minutes to 5 hours.
After completion of the reaction, compound [III-3] can be isolated by performing operations such as pouring the reaction mixture into water, extracting the mixture with an organic solvent, and then concentrating the mixture. The isolated compound [III-3] can be further purified by column chromatography, recrystallization, and the like, if necessary.
＜中間体の製造方法２＞
　一般式［ＩＩＩ－１］で表される化合物は、例えば一般式［ＩＩＩ－３］で表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Method 2 for producing intermediate>
The compound represented by the general formula [III-1] can be produced, for example, using a compound represented by the general formula [III-3] according to a method comprising the following reaction formula.
Figure JPOXMLDOC01-appb-C000093
Figure JPOXMLDOC01-appb-C000093
　（式中、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒａ、Ｒｂ、Ｌ１、Ｌ３及びｎは前記と同じ意味を示す。） (In the formula, R 3 , R 4 , R 5 , R 6 , R a , R b , L 1 , L 3 and n have the same meaning as described above.)
　（工程２’－１）
　即ち、一般式［ＩＩＩ－１］で表される化合物は、一般式［ＩＩＩ－３］で表される化合物と化合物［ＩＶ－２０］又は化合物［ＩＶ－２１］とを、適当な酸触媒の存在下又は非存在下、適当な溶媒中において反応させることにより一般式［ＩＩＩ－９］で表される化合物とした後、ハロゲン化剤で反応させることにより製造することができる。
　本工程で使用する化合物［ＩＶ－２０］又は化合物［ＩＶ－２１］の使用量は、化合物［ＩＩＩ－３］１モルに対して１～５モルの範囲から適宜選択すればよく、好ましくは１．０～１．２モルである。
　本工程で使用できる酸触媒は、例えば、メタンスルホン酸又はｐ－トルエンスルホン酸等のスルホン酸類、四塩化チタン等のルイス酸等が挙げられる。尚、酸触媒の使用量は、化合物［ＩＩＩ－３］１モルに対して０．００１～５モルの範囲から適宜選択すればよく、好ましくは０．０１～１．２モルである。
　本工程で使用できる溶媒としては、例えば、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、メタノール、エタノール、２－プロパノールイソプロピルアルコール等のアルコール類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類、ピリジン、ピコリン等のピリジン類又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［ＩＩＩ－３］１モルに対して０．１～１００リットルであり、好ましくは０．３～１０リットルである。
　本工程で使用するハロゲン化剤は、例えば、塩素、Ｎ－クロロコハク酸イミド、Ｎ－ブロモコハク酸イミド、次亜塩素酸ｔｅｒｔ－ブチル等が挙げられる。尚、ハロゲン化剤の使用量は、化合物［ＩＩＩ－９］１モルに対して１～５モルの範囲から適宜選択すればよく、好ましくは１．０～１．１モルである。
　本工程の反応温度は、－７０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは－２０℃～１００℃の範囲で行うのがよい。
　本工程の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１５分～２４時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［ＩＩＩ－１］を単離することができる。単離した化合物［ＩＩＩ－１］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 2'-1)
That is, the compound represented by the general formula [III-1] is obtained by converting the compound represented by the general formula [III-3] and the compound [IV-20] or the compound [IV-21] to a suitable acid catalyst. The compound represented by the general formula [III-9] can be produced by reacting in a suitable solvent in the presence or absence of the compound, and then reacting with a halogenating agent.
The amount of compound [IV-20] or compound [IV-21] used in this step may be appropriately selected from the range of 1 to 5 mol per 1 mol of compound [III-3], and is preferably 1 0.0 to 1.2 mol.
Examples of the acid catalyst that can be used in this step include sulfonic acids such as methanesulfonic acid and p-toluenesulfonic acid, and Lewis acids such as titanium tetrachloride. The amount of the acid catalyst to be used may be appropriately selected from the range of 0.001 to 5 mol, and preferably 0.01 to 1.2 mol, per 1 mol of compound [III-3].
Examples of the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like Aprotic polar solvents, alcohols such as methanol, ethanol, 2-propanol isopropyl alcohol, aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane, pyridines such as pyridine and picoline, or a mixture thereof. The solvent and the like. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-3].
Examples of the halogenating agent used in this step include chlorine, N-chlorosuccinimide, N-bromosuccinimide, tert-butyl hypochlorite and the like. The amount of the halogenating agent to be used may be appropriately selected from the range of 1 to 5 mol per 1 mol of the compound [III-9], and is preferably 1.0 to 1.1 mol.
The reaction temperature in this step may be selected from an arbitrary temperature range from −70 ° C. to the reflux temperature in the reaction system, and is preferably from −20 ° C. to 100 ° C.
The reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 15 minutes to 24 hours.
After completion of the reaction, compound [III-1] can be isolated by performing operations such as pouring the reaction mixture into water, extracting with an organic solvent, and then concentrating the mixture. The isolated compound [III-1] can be further purified, if necessary, by column chromatography, recrystallization and the like.
　（工程２’－２）
　また、一般式［ＩＩＩ－１］で表される化合物は、一般式［ＩＩＩ－３］で表される化合物と化合物［ＩＶ－２２］とを、適当な塩基の存在下又は非存在下、適当な溶媒において反応させることにより一般式［ＩＩＩ－１０］で表される化合物とした後、ハロゲン化剤で反応させるにより製造することができる。
　本工程で使用する化合物［ＩＶ－２２］の使用量は、化合物［ＩＩＩ－３］１モルに対して１～１５モルの範囲から適宜選択すればよく、好ましくは１．０～７．０モルである。
　本工程で使用できる塩基は、例えば、水酸化ナトリウム、水酸化カリウム、水酸化リチウム等のアルカリ金属の水酸化物類、水酸化カルシウム、水酸化マグネシウム等のアルカリ土類金属の水酸化物類、炭酸ナトリウム、炭酸カリウム等のアルカリ金属の炭酸塩類、炭酸水素ナトリウム、炭酸水素カリウム等のアルカリ金属の重炭酸塩類等の無機塩基類、水素化ナトリウム、水素化カリウム等の金属水素化物類、ナトリウムメトキシド、ナトリウムエトキシド、カリウムｔｅｒｔ－ブトキシド等のアルコールの金属塩類、又はトリエチルアミン、Ｎ，Ｎ－ジメチルアニリン、ピリジン、４－Ｎ，Ｎ－ジメチルアミノピリジン、１，８－ジアザビシクロ［５，４，０］－７－ウンデセン等の有機塩基類等が挙げられる。尚、塩基の使用量は、化合物［ＩＩＩ－３］１モルに対して１～１０モルの範囲から適宜選択すればよく、好ましくは１．０～１．２モルである。
　本工程で使用できる溶媒としては、例えば、ジエチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、２－メチルテトラヒドロフラン、１，４－ジオキサン等のエーテル類、ベンゼン、トルエン、キシレン、クロロベンゼン等の芳香族炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、メタノール、エタノール、２－プロパノール等のアルコール類、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、酢酸エチル等のエステル類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類、ピリジン、ピコリン等のピリジン類又はこれらの混合溶媒等が挙げられる。尚、溶媒の使用量は、化合物［ＩＩＩ－３］１モルに対して０．１～１００リットルであり、好ましくは０．３～１０リットルである。
　本工程で使用できるハロゲン化剤は、例えば、三塩化リン、三臭化リン、塩化チオニル、オキシ塩化リン、五塩化リン、トリフェニルホスフィン／ 四塩化炭素又はトリフェニルホスフィン／ 四臭化炭素等が挙げられる。尚、ハロゲン化剤の使用量は、化合物［ＩＩＩ－１０］１モルに対して１モルから溶媒量相当の範囲から適宜選択すればよく、好ましくは１．０～５．０モルである。
　本工程の反応温度は、－７０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは－２０℃～１００℃の範囲で行うのがよい。
　本工程の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１５分～２４時間である。
　反応終了後は、反応混合物を水に注加し、有機溶媒にて抽出してから、濃縮する等の操作を行うことにより、化合物［ＩＩＩ－１］を単離することができる。または反応混合物から溶媒を濃縮する事でも化合物［ＩＩＩ－１］を単離することができる。単離した化合物［ＩＩＩ－１］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 (Step 2'-2)
Further, the compound represented by the general formula [III-1] can be prepared by converting the compound represented by the general formula [III-3] and the compound [IV-22] in the presence or absence of a suitable base. The compound represented by the general formula [III-10] can be produced by reacting with a suitable solvent and then reacting with a halogenating agent.
The amount of compound [IV-22] used in this step may be appropriately selected from the range of 1 to 15 mol per 1 mol of compound [III-3], and is preferably 1.0 to 7.0 mol. It is.
Bases that can be used in this step include, for example, hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide and lithium hydroxide, hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide, Inorganic bases such as alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydrides such as sodium hydride and potassium hydride; sodium methoxy Metal salts of alcohols such as sodium, sodium ethoxide and potassium tert-butoxide, or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5,4,0 And organic bases such as -7-undecene. The amount of the base used may be appropriately selected from the range of 1 to 10 mol per 1 mol of compound [III-3], and is preferably 1.0 to 1.2 mol.
Examples of the solvent that can be used in this step include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like Aprotic polar solvents, alcohols such as methanol, ethanol and 2-propanol, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, esters such as ethyl acetate, pentane, hexane, cyclohexyl Emissions, aliphatic hydrocarbons such as heptane, pyridine, pyridine or a mixed solvent of these picoline, and the like. The amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [III-3].
Examples of the halogenating agent that can be used in this step include phosphorus trichloride, phosphorus tribromide, thionyl chloride, phosphorus oxychloride, phosphorus pentachloride, triphenylphosphine / carbon tetrachloride, or triphenylphosphine / carbon tetrabromide. No. The amount of the halogenating agent to be used may be appropriately selected from the range of 1 mol to the amount of the solvent relative to 1 mol of compound [III-10], and is preferably 1.0 to 5.0 mol.
The reaction temperature in this step may be selected from an arbitrary temperature range from −70 ° C. to the reflux temperature in the reaction system, and is preferably from −20 ° C. to 100 ° C.
The reaction time of this step varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually 15 minutes to 24 hours.
After completion of the reaction, compound [III-1] can be isolated by performing operations such as pouring the reaction mixture into water, extracting with an organic solvent, and then concentrating the mixture. Alternatively, compound [III-1] can also be isolated by concentrating the solvent from the reaction mixture. The isolated compound [III-1] can be further purified, if necessary, by column chromatography, recrystallization and the like.
＜中間体の製造方法３＞
　一般式［ＩＩＩ－５］で表される化合物は、例えば一般式［ＩＩＩ－１１］で表される化合物を用いて下記に例示する反応式からなる方法に従い製造することができる。 <Method 3 for producing an intermediate>
The compound represented by the general formula [III-5] can be produced, for example, using a compound represented by the general formula [III-11] according to a method comprising the following reaction formula.
Figure JPOXMLDOC01-appb-C000094
Figure JPOXMLDOC01-appb-C000094
　（式中、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｘ及びｎは前記と同じ意味を示す。） (In the formula, R 3 , R 4 , R 5 , R 6 , X and n have the same meanings as described above.)
　即ち、一般式［ＩＩＩ－５］で表される化合物は、一般式［ＩＩＩ－１１］で表される化合物とハロゲン化剤とを、適当な溶媒中において反応させることにより製造することができる。
　本反応で使用できるハロゲン化剤としては、塩素、塩化スルフリル、Ｎ－クロロコハク酸イミド、臭素、Ｎ－ブロモコハク酸イミド、１，３－ジブロモ－５，５－ヒダントイン、沃素、Ｎ－ヨードコハク酸イミド、１，３－ジヨード－５，５－ヒダントイン等を挙げることができる。尚、ハロゲン化剤の使用量は、化合物［ＩＩＩ－１１］１モルに対して０．５～１０モルの範囲から適宜選択すればよく、好ましくは０．５～２．０モルである。
　本反応で使用できる溶媒としては、例えば、ジクロロメタン、クロロホルム、１，２－ジクロロエタン等のハロゲン化炭化水素類、ペンタン、ヘキサン、シクロヘキサン、ヘプタン等の脂肪族炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、ジメチルスルホキシド、スルホラン、１，３－ジメチル－２－イミダゾリジノン等の非プロトン性極性溶媒類、酢酸、プロピオン酸、トリフルオロ酢酸等のカルボン酸類、硫酸、水、又はこれらの混合溶媒等を挙げることができる。尚、溶媒の使用量は、化合物［ＩＩＩ－１１］１モルに対して０．１～３００リットルであり、好ましくは０．３～２０リットルである。
　本反応の反応温度は、通常－７０℃から反応系における還流温度までの任意の温度の範囲から選択すればよく、好ましくは―２０℃～１００℃の範囲で行うのがよい。
　本反応の反応時間は、反応温度、反応基質、反応量等により異なるが、通常１０分～２４時間である。
　反応終了後は、反応混合物を水に注加し、析出した固体を濾取する又は有機溶媒にて抽出してから濃縮する等の操作を行うことにより、化合物［ＩＩＩ－５］を単離することができる。単離した化合物［ＩＩＩ－５］は、必要に応じてカラムクロマトグラフィー、再結晶等により更に精製することもできる。 That is, the compound represented by the general formula [III-5] can be produced by reacting the compound represented by the general formula [III-11] with a halogenating agent in a suitable solvent.
Halogenating agents usable in this reaction include chlorine, sulfuryl chloride, N-chlorosuccinimide, bromine, N-bromosuccinimide, 1,3-dibromo-5,5-hydantoin, iodine, N-iodosuccinimide, 1,3-diiodo-5,5-hydantoin and the like can be mentioned. The amount of the halogenating agent to be used may be appropriately selected from the range of 0.5 to 10 mol, preferably 0.5 to 2.0 mol, per 1 mol of compound [III-11].
Examples of the solvent that can be used in this reaction include halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; acetonitrile, propionitrile; Aprotic polar solvents such as nitriles, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone; Examples thereof include carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid, sulfuric acid, water, and a mixed solvent thereof. The amount of the solvent to be used is 0.1-300 liter, preferably 0.3-20 liter, per 1 mol of compound [III-11].
The reaction temperature of this reaction may be selected from an arbitrary temperature range from -70 ° C to the reflux temperature in the reaction system, and is preferably from -20 ° C to 100 ° C.
The reaction time of this reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount and the like, but is usually from 10 minutes to 24 hours.
After completion of the reaction, the compound [III-5] is isolated by performing operations such as pouring the reaction mixture into water, and collecting the precipitated solid by filtration or extraction with an organic solvent and concentration. be able to. The isolated compound [III-5] can be further purified, if necessary, by column chromatography, recrystallization and the like.
　本発明の一般式［ＩＩ］で表される３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸誘導体又はそのエステル体は、本発明の一般式［Ｉ］で表される３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩を製造する際の中間体として有用な化合物である。 The 3- (1H-1,2,4-triazol-1-yl) benzoic acid derivative represented by the general formula [II] of the present invention or an ester thereof is represented by the general formula [I] of the present invention. 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or a compound useful as an intermediate in producing an agriculturally acceptable salt thereof.
　また、本発明の一般式［ＩＩＩ］で表される１－フェニル－１Ｈ－１，２，４－トリアゾール誘導体は、本発明の一般式［ＩＩ］で表される３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸誘導体又はそのエステル体を製造する際の中間体として有用な化合物である。 Further, the 1-phenyl-1H-1,2,4-triazole derivative represented by the general formula [III] of the present invention is a 3- (1H-1,2) represented by the general formula [II] of the present invention. , 4-triazol-1-yl) benzoic acid derivative or an ester thereof, which is useful as an intermediate.
　本発明の農薬組成物は、本発明の一般式［Ｉ］で表される３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩を有効成分として含有する。 The pesticidal composition of the present invention comprises a 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative represented by the general formula [I] of the present invention or an agriculturally acceptable salt thereof. Contains as an active ingredient.
　本発明の農薬組成物は、必要に応じ、農薬製剤に通常用いられる添加成分（担体）を含有することができる。 農 The pesticidal composition of the present invention can contain, if necessary, additional components (carriers) usually used in pesticide preparations.
　本発明の有害生物防除剤は、本発明の一般式［Ｉ］で表される３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩を有効成分として含有する。本発明の有害生物防除剤は、代表的には殺虫剤、殺ダニ剤及び殺センチュウ剤である。 The pest control agent of the present invention is a 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative represented by the general formula [I] of the present invention or an agriculturally acceptable salt thereof. As an active ingredient. The pesticides of the present invention are typically insecticides, acaricides and nematocides.
　本発明の有害生物防除剤は、必要に応じ、農薬製剤に通常用いられる添加成分（担体）を含有することができる。 有害 The pest control agent of the present invention can contain, as necessary, an additive component (carrier) usually used in agricultural chemical formulations.
　この添加成分としては、固体担体又は液体担体等の担体、界面活性剤、結合剤や粘着付与剤、増粘剤、着色剤、拡展剤、展着剤、凍結防止剤、固結防止剤、崩壊剤、分解防止剤等が挙げられ、その他必要に応じ、防腐剤や、植物片等を添加成分に用いてもよい。又、これらの添加成分は１種用いてもよいし、又、２種以上を組み合わせて用いてもよい。 As the additional component, a carrier such as a solid carrier or a liquid carrier, a surfactant, a binder or a tackifier, a thickener, a coloring agent, a spreading agent, a spreading agent, an antifreezing agent, an anti-caking agent, Disintegrators, decomposition inhibitors and the like can be mentioned, and if necessary, preservatives, plant fragments and the like may be used as additional components. These additional components may be used alone or in combination of two or more.
　以下に、上記添加成分について説明する。 上 記 The following describes the additional components.
　固体担体としては、例えば、パイロフィライトクレー、カオリンクレー、硅石クレー、タルク、珪藻土、ゼオライト、ベントナイト、酸性白土、活性白土、アタパルガスクレー、バーミキュライト、パーライト、軽石、ホワイトカーボン（合成ケイ酸、合成ケイ酸塩等）、二酸化チタン等の鉱物系担体；木質粉、トウモロコシ茎、クルミ殻、果実核、モミガラ、オガクズ、フスマ、大豆粉、粉末セルロース、デンプン、デキストリン、糖類等の植物性担体；炭酸カルシウム、硫酸アンモニウム、硫酸ナトリウム、塩化カリウム等の無機塩類担体；ポリエチレン、ポリプロピレン、ポリ塩化ビニル、ポリ酢酸ビニル、エチレン－酢酸ビニル共重合体、尿素－アルデヒド樹脂等の高分子担体等を挙げることができる。 Solid carriers include, for example, pyrophyllite clay, kaolin clay, silica clay, talc, diatomaceous earth, zeolite, bentonite, acid clay, activated clay, attapulgase clay, vermiculite, perlite, pumice, white carbon (synthetic silicic acid, Mineral carriers such as synthetic silicates) and titanium dioxide; vegetable carriers such as wood flour, corn stalk, walnut shell, fruit nucleus, peach, sawdust, bran, soy flour, powdered cellulose, starch, dextrin, saccharides and the like; Inorganic salt carriers such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride; and polymer carriers such as polyethylene, polypropylene, polyvinyl chloride, polyvinyl acetate, ethylene-vinyl acetate copolymer, and urea-aldehyde resins. it can.
　液体担体としては、例えば、メタノール、エタノール、プロパノール、２－プロパノール、ブタノール、シクロヘキサノール等の一価アルコール類；エチレングリコール、ジエチレングリコール、プロピレングリコール、ヘキシレングリコール、ポリエチレングリコール、ポリプロピレングリコール、グリセリン等の多価アルコール類；プロピレン系グリコールエーテル等の多価アルコール誘導体類；アセトン、メチルエチルケトン、メチルイソブチルケトン、ジイソブチルケトン、シクロヘキサノン、イソホロン等のケトン類；エチルエーテル、１，４－ジオキサン、セロソルブ、ジプロピルエーテル、テトラヒドロフラン等のエーテル類；ノルマルパラフィン、ナフテン、イソパラフィン、ケロシン、鉱油等の脂肪族炭化水素類；トルエン、Ｃ９－Ｃ１０アルキルベンゼン、キシレン、ソルベントナフサ、アルキルナフタレン、高沸点芳香族炭化水素等の芳香族炭化水素類；１，２－ジクロロエタン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類；酢酸エチル、ジイソプロピルフタレート、ジブチルフタレート、ジオクチルフタレート、アジピン酸ジメチル等のエステル類；γ－ブチロラクトン等のラクトン類；Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジエチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン等のアミド類；アセトニトリル等のニトリル類；ジメチルスルホキシド等の硫黄化合物類；大豆油、ナタネ油、綿実油、ヤシ油、ヒマシ油等の植物油；水等を挙げることができる。 Examples of the liquid carrier include monohydric alcohols such as methanol, ethanol, propanol, 2-propanol, butanol, and cyclohexanol; and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin. Polyhydric alcohol derivatives such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone and isophorone; ethyl ether, 1,4-dioxane, cellosolve, dipropyl ether; Ethers such as tetrahydrofuran; aliphatic hydrocarbons such as normal paraffin, naphthene, isoparaffin, kerosene and mineral oil; , C 9 -C 10 alkylbenzene, xylene, solvent naphtha, alkylnaphthalene, aromatic hydrocarbons such as high-boiling aromatic hydrocarbons; 1,2-dichloroethane, chloroform, halogenated hydrocarbons such as carbon tetrachloride, acetic acid Esters such as ethyl, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate; lactones such as γ-butyrolactone; N, N-dimethylformamide, N, N-diethylformamide, N, N-dimethylacetamide, N- Amides such as methyl-2-pyrrolidone; nitriles such as acetonitrile; sulfur compounds such as dimethyl sulfoxide; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, coconut oil, castor oil; and water.
　界面活性剤としては、特に制限されないが、好ましくは水中でゲル化するか、或いは膨潤性を示すものであり、例えば、ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ショ糖脂肪酸エステル、ポリオキシエチレン脂肪酸エステル、ポリオキシエチレン樹脂酸エステル、ポリオキシエチレン脂肪酸ジエステル、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルフェニルエーテル、ポリオキシエチレンジアルキルフェニルエーテル、ポリオキシエチレンアルキルフェニルエーテルホルマリン縮合物、ポリオキシエチレンポリオキシプロピレンブロックポリマー、アルキルポリオキシエチレンポリプロピレンブロックポリマーエーテル、ポリオキシエチレンアルキルアミン、ポリオキシエチレン脂肪酸アミド、ポリオキシエチレン脂肪酸ビスフェニルエーテル、ポリアルキレンベンジルフェニルエーテル、ポリオキシアルキレンスチリルフェニルエーテル、アセチレンジオール、ポリオキシアルキレン付加アセチレンジオール、ポリオキシエチレンエーテル型シリコーン、エステル型シリコーン、フッ素系界面活性剤、ポリオキシエチレンひまし油、ポリオキシエチレン硬化ひまし油等の非イオン性界面活性剤；アルキル硫酸塩、ポリオキシエチレンアルキルエーテル硫酸塩、ポリオキシエチレンアルキルフェニルエーテル硫酸塩、ポリオキシエチレンスチリルフェニルエーテル硫酸塩、アルキルベンゼンスルホン酸塩、リグニンスルホン酸塩、アルキルスルホコハク酸塩、ナフタレンスルホン酸塩、アルキルナフタレンスルホン酸塩、ナフタレンスルホン酸のホルマリン縮合物の塩、アルキルナフタレンスルホン酸のホルマリン縮合物の塩、脂肪酸塩、ポリカルボン酸塩、Ｎ－メチル－脂肪酸サルコシネート、樹脂酸塩、ポリオキシエチレンアルキルエーテルリン酸塩、ポリオキシエチレンアルキルフェニルエーテルリン酸塩等のアニオン性界面活性剤；ラウリルアミン塩酸塩、ステアリルアミン塩酸塩、オレイルアミン塩酸塩、ステアリルアミン酢酸塩、ステアリルアミノプロピルアミン酢酸塩、アルキルトリメチルアンモニウムクロライド、アルキルジメチルベンザルコニウムクロライド等のアルキルアミン塩等のカチオン界面活性剤；ジアルキルジアミノエチルベタイン、アルキルジメチルベンジルベタイン等のベタイン型、ジアルキルアミノエチルグリシン、アルキルジメチルベンジルグリシン等アミノ酸型等の両性界面活性剤等を挙げることができる。 The surfactant is not particularly limited, but is preferably one that gels in water or exhibits swelling properties, for example, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene Fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene poly Oxypropylene block polymer, alkyl polyoxyethylene polypropylene block polymer ether, polyoxyethylene alkylamine, polyoxyethylene Fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol, polyoxyalkylene-added acetylene diol, polyoxyethylene ether type silicone, ester type silicone, fluorine surfactant Surfactants such as polyoxyethylene castor oil and polyoxyethylene hardened castor oil; alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene styryl phenyl ether sulfates , Alkylbenzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate Salt of formalin condensate of naphthalenesulfonic acid, salt of formalin condensate of alkylnaphthalenesulfonic acid, fatty acid salt, polycarboxylate, N-methyl-fatty acid sarcosinate, resinate, polyoxyethylene alkyl ether phosphate, poly Anionic surfactants such as oxyethylene alkylphenyl ether phosphate; laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, alkyldimethylbenza Cationic surfactants such as alkylamine salts such as ruconium chloride; betaine type such as dialkyldiaminoethylbetaine and alkyldimethylbenzylbetaine; dialkylaminoethylglycine; And amphoteric surfactants such as amino acid type such as dimethylbenzylglycine.
　結合剤や粘着付与剤としては、例えば、カルボキシメチルセルロースやその塩、デキストリン、水溶性デンプン、キサンタンガム、グアーガム、蔗糖、ポリビニルピロリドン、アラビアゴム、ポリビニルアルコール、ポリビニルアセテート、ポリアクリル酸ナトリウム、平均分子量６０００～２００００のポリエチレングリコール、平均分子量１０万～５００万のポリエチレンオキサイド、天然燐脂質（例えばセファリン酸、レシチン等）等を挙げることができる。 Examples of the binder and tackifier include carboxymethylcellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6,000 to Examples include polyethylene glycol having a molecular weight of 20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, and natural phospholipids (eg, cephalic acid, lecithin, etc.).
　増粘剤としては、例えば、キサンタンガム、グアーガム、カルボキシメチルセルロース、ポリビニルピロリドン、カルボキシビニルポリマー、アクリル系ポリマー、デンプン誘導体、多糖類のような水溶性高分子；高純度ベントナイト、ホワイトカーボンのような無機微粉等を挙げることができる。 Examples of the thickener include water-soluble polymers such as xanthan gum, guar gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch derivative, and polysaccharide; inorganic fine powders such as high-purity bentonite and white carbon And the like.
　着色剤としては、例えば、酸化鉄、酸化チタン、プルシアンブルーのような無機顔料；アリザリン染料、アゾ染料、金属フタロシアニン染料のような有機染料等を挙げることができる。 Examples of the coloring agent include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue; and organic dyes such as alizarin dye, azo dye, and metal phthalocyanine dye.
　拡展剤としては、例えば、シリコーン系界面活性剤、セルロース粉末、デキストリン、加工デンプン、ポリアミノカルボン酸キレート化合物、架橋ポリビニルピロリドン、マレイン酸とスチレン類、メタアクリル酸共重合体、多価アルコールのポリマーとジカルボン酸無水物とのハーフエステル、ポリスチレンスルホン酸の水溶性塩等を挙げることができる。 Examples of the spreading agent include silicone surfactants, cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, cross-linked polyvinyl pyrrolidone, maleic acid and styrenes, methacrylic acid copolymers, and polymers of polyhydric alcohols. And a diester of a dicarboxylic acid, and a water-soluble salt of polystyrenesulfonic acid.
　展着剤としては、例えば、ジアルキルスルホコハク酸ナトリウム、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルフェニルエーテル、ポリオキシエチレン脂肪酸エステルなどの種々の界面活性剤；パラフィン、テルペン、ポリアミド樹脂、ポリアクリル酸塩、ポリオキシエチレン、ワックス、ポリビニルアルキルエーテル、アルキルフェノールホルマリン縮合物、合成樹脂エマルション等を挙げることができる。 Examples of the spreading agent include various surfactants such as sodium dialkyl sulfosuccinate, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, and polyoxyethylene fatty acid ester; paraffin, terpene, polyamide resin, polyacrylate , Polyoxyethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, synthetic resin emulsion and the like.
　凍結防止剤としては、例えば、エチレングリコール、ジエチレングリコール、プロピレングリコール、グリセリン等の多価アルコール類等を挙げることができる。 Examples of the antifreeze include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
　固結防止剤としては、例えば、デンプン、アルギン酸、マンノース、ガラクトース等の多糖類；ポリビニルピロリドン、ホワイトカーボン、エステルガム、石油樹脂等を挙げることができる。 Examples of the anti-caking agent include polysaccharides such as starch, alginic acid, mannose and galactose; polyvinylpyrrolidone, white carbon, ester gum, petroleum resin and the like.
　崩壊剤としては、例えば、トリポリリン酸ソーダ、ヘキサメタリン酸ソーダ、ステアリン酸金属塩、セルロース粉末、デキストリン、メタクリル酸エステルの共重合体、ポリビニルピロリドン、ポリアミノカルボン酸キレート化合物、スルホン化スチレン・イソブチレン・無水マレイン酸共重合体、デンプン・ポリアクリロニトリルグラフト共重合体等を挙げることができる。 Examples of the disintegrating agent include sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, a copolymer of methacrylic acid ester, polyvinylpyrrolidone, a polyaminocarboxylic acid chelate compound, and sulfonated styrene / isobutylene / maleic anhydride. Acid copolymers and starch / polyacrylonitrile graft copolymers can be exemplified.
　分解防止剤としては、例えば、ゼオライト、生石灰、酸化マグネシウムのような乾燥剤；フェノール系、アミン系、硫黄系、リン酸系等の酸化防止剤；サリチル酸系、ベンゾフェノン系等の紫外線吸収剤等を挙げることができる。 Examples of the decomposition inhibitor include desiccants such as zeolite, quicklime, and magnesium oxide; phenol-based, amine-based, sulfur-based, and phosphoric acid-based antioxidants; and salicylic acid-based and benzophenone-based ultraviolet absorbers. Can be mentioned.
　一方、本発明の有害生物防除剤において、上記添加成分を含有させる場合、その含有割合については、質量基準で、固体担体又は液体担体等の担体では通常５～９５％、好ましくは２０～９０％の範囲で選ばれ、界面活性剤では通常０．１％～３０％、好ましくは０．５～１０％の範囲で選ばれ、その他の添加剤は０．１～３０％、好ましくは０．５～１０％の範囲で選ばれる。 On the other hand, when the above-mentioned additive component is contained in the pesticidal composition of the present invention, the content thereof is usually 5 to 95%, preferably 20 to 90% for a carrier such as a solid carrier or a liquid carrier on a mass basis. The surfactant is usually selected in the range of 0.1% to 30%, preferably 0.5 to 10%, and the other additives are 0.1 to 30%, preferably 0.5 to 30%. It is selected in the range of １０10%.
　本発明の有害生物防除剤は、粉剤、粉粒剤、粒剤、水和剤、水溶剤、顆粒水和剤、錠剤、ジャンボ剤、乳剤、油剤、液剤、フロアブル剤、エマルジョン剤、マイクロエマルジョン剤、サスポエマルジョン剤、微量散布剤、マイクロカプセル剤、くん煙剤、エアロゾル剤、ベイト剤、ペースト剤等の任意の剤型に製剤化して使用される。 The pest control agent of the present invention includes powders, powders and granules, granules, wettable powders, aqueous solvents, wettable granules, tablets, jumbo, emulsions, oils, liquids, flowables, emulsions, microemulsions , Suspoemulsion, microdispersion, microcapsule, smoke agent, aerosol, bait, paste and the like.
　これらの製剤の実際の使用に際しては、そのまま使用するか、又は、水等の希釈剤で所定濃度に希釈して使用することができる。本発明の化合物を含有する種々の製剤又はその希釈物の施用は、通常一般に行われている施用方法、即ち、散布（例えば、噴霧、ミスティング、アトマイジング、散粉、散粒、水面施用、箱施用等）、土壌施用（例えば、混入、潅注等）、表面施用（例えば、塗布、粉衣、被覆等）、種子処理（例えば、塗沫、粉衣処理等）、浸漬、毒餌、くん煙施用等により行うことができる。又、家畜に対して前記有効成分を飼料に混合して与え、その排泄物での有害虫、特に有害昆虫の発生、成育を防除することも可能である。 When these preparations are actually used, they can be used as they are or diluted to a predetermined concentration with a diluent such as water. The application of various preparations containing the compound of the present invention or a dilution thereof can be carried out by a commonly used application method, that is, spraying (eg, spraying, misting, atomizing, dusting, dusting, water application, box application) Application), soil application (for example, mixing, irrigation, etc.), surface application (for example, application, dressing, coating, etc.), seed treatment (for example, smearing, dressing, etc.), immersion, poison bait, smoke application And the like. It is also possible to feed the livestock with the above-mentioned active ingredient by mixing it with the feed to control the generation and growth of harmful insects, particularly harmful insects, in their excrement.
　本発明の有害生物の防除方法は、前記した施用方法で本発明の一般式［Ｉ］で表される３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩の有効成分量を使用することにより行うことができる。 The pest control method of the present invention is a method for controlling a pest according to the above-mentioned application method, wherein the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative represented by the general formula [I] of the present invention or a derivative thereof is used. It can be carried out by using an amount of an active ingredient of an agriculturally acceptable salt.
　本発明の有害生物防除剤における有効成分の配合割合（質量％）については、必要に応じて適宜選ばれる。例えば、粉剤、粉粒剤、微粒剤等とする場合は０．０１～２０％、好ましくは０．０５～１０％の範囲から適宜選ぶのがよく、粒剤等とする場合は０．１～３０％、好ましくは０．５～２０％の範囲から適宜選ぶのがよく、水和剤、顆粒水和剤等とする場合は１～７０％、好ましくは５～５０％の範囲から適宜選ぶのがよく、水溶剤、液剤等とする場合は１～９５％、好ましくは１０～８０％の範囲から適宜選ぶのがよく、乳剤等とする場合は５～９０％、好ましくは１０～８０％の範囲から適宜選ぶのがよく、油剤等とする場合は１～５０％、好ましくは５～３０％の範囲から適宜選ぶのがよく、フロアブル剤等とする場合は５～６０％、好ましくは１０～５０％の範囲から適宜選ぶのがよく、エマルジョン剤、マイクロエマルジョン剤、サスポエマルジョン剤等とする場合は５～７０％、好ましくは１０～６０％の範囲から適宜選ぶのがよく、錠剤、ベイト剤、ペースト剤等とする場合は、１～８０％、好ましくは５～５０％の範囲から適宜選ぶのがよく、くん煙剤等とする場合は、０．１～５０％、好ましくは１～３０％の範囲から適宜選ぶのがよく、エアロゾル剤等とする場合は、０．０５～２０％、好ましくは０．１～１０％の範囲から適宜選ぶのがよい。 配合 The mixing ratio (% by mass) of the active ingredient in the pest control agent of the present invention is appropriately selected as necessary. For example, in the case of a powder, a granule, a fine granule or the like, it is appropriate to appropriately select from the range of 0.01 to 20%, preferably 0.05 to 10%. It is appropriate to appropriately select from the range of 30%, preferably from 0.5 to 20%, and in the case of a wettable powder, a wettable powder, etc., it is appropriately selected from the range of 1 to 70%, preferably 5 to 50%. In the case of a water solvent or a liquid preparation, it may be appropriately selected from the range of 1 to 95%, preferably 10 to 80%, and in the case of an emulsion or the like, 5 to 90%, preferably 10 to 80%. It is preferable to select an appropriate amount from the range. When it is used as an oil agent, it is appropriately selected from the range of 1 to 50%, preferably 5 to 30%. It is preferable to select an appropriate one from the range of 50%, and an emulsion, a microemulsion, In the case of a spoemulsion or the like, it is appropriate to appropriately select from the range of 5 to 70%, preferably 10 to 60%. It is preferable to appropriately select from the range of 50%, and in the case of a smoke agent, etc., it is appropriate to select from the range of 0.1 to 50%, preferably in the range of 1 to 30%. It is appropriate to appropriately select from the range of 0.05 to 20%, preferably 0.1 to 10%.
　これらの製剤は、適当な濃度に希釈して散布するか、又は、直接施用する。 製 剤 These preparations are diluted to an appropriate concentration and sprayed or applied directly.
　本発明の有害生物防除剤の施用は、希釈剤で希釈して使用する場合には、一般に０．１～５０００ｐｐｍの有効成分濃度で行う。製剤をそのまま使用する場合の単位面積あたりの施用量は、有効成分化合物として１ｈａ当り０．１～５０００ｇで使用されるが、これらに限定されるものではない。 有害 When the pest control agent of the present invention is used after being diluted with a diluent, it is generally used at an active ingredient concentration of 0.1 to 5000 ppm. When the preparation is used as it is, the application rate per unit area is 0.1 to 5000 g per ha as the active ingredient compound, but is not limited thereto.
　尚、本発明の有害生物防除剤は、本発明の化合物を単独で有効成分としても十分有効であることはいうまでもないが、必要に応じて他の肥料、農薬、例えば、殺虫剤、殺ダニ剤、殺センチュウ剤、共力剤、殺菌剤、抗ウイルス剤、誘引剤、除草剤、植物生長調整剤などと混用、併用することができ、この場合に一層優れた効果を示すこともある。 Needless to say, the pesticidal agent of the present invention is sufficiently effective even when the compound of the present invention is used alone as an active ingredient. However, if necessary, other fertilizers and pesticides, for example, insecticides, pesticides, It can be mixed and used in combination with mites, nematicides, synergists, fungicides, antivirals, attractants, herbicides, plant growth regulators, etc., in which case even better effects may be exhibited. .
　次に、混合又は併用してもよい公知の殺虫剤、殺ダニ剤、殺センチュウ剤、共力剤化合物を例示する。 Next, known insecticides, acaricides, nematocides, and synergist compounds that may be mixed or used in combination are exemplified.
　殺虫活性成分：
　アクリナトリン（ａｃｒｉｎａｔｈｒｉｎ）、アザジラクチン（ａｚａｄｉｒａｃｈｔｉｎ）、アザメチホス（ａｚａｍｅｔｈｉｐｈｏｓ）、アシノナピル（ａｃｙｎｏｎａｐｙｒ）、アジンホス・エチル（ａｚｉｎｐｈｏｓ－ｅｔｈｙｌ）、アジンホス・メチル（ａｚｉｎｐｈｏｓ－ｍｅｔｈｙｌ）、アセキノシル（ａｃｅｑｕｉｎｏｃｙｌ）、アセタミプリド（ａｃｅｔａｍｉｐｒｉｄ）、アセトプロール（ａｃｅｔｏｐｒｏｌｅ）、アセフェート（ａｃｅｐｈａｔｅ）、アゾシクロチン（ａｚｏｃｙｃｌｏｔｉｎ）、アバメクチン（ａｂａｍｅｃｔｉｎ）、アフィドピロペン（ａｆｉｄｏｐｙｒｏｐｅｎ）、アフォキソレイナー（ａｆｏｘｏｌａｎｅｒ）、アミドフルメット（ａｍｉｄｏｆｌｕｍｅｔ）、アミトラズ（ａｍｉｔｒａｚ）、アラニカルブ（ａｌａｎｙｃａｒｂ）、アルジカルブ（ａｌｄｉｃａｒｂ）、アルドキシカルブ（ａｌｄｏｘｙｃａｒｂ）、アレスリン（ａｌｌｅｔｈｒｉｎ）［ｄ－ｃｉｓ－ｔｒａｎｓ－体、ｄ－ｔｒａｎｓ－体を含む］、イサゾホス（ｉｓａｚｏｐｈｏｓ）、イサミドホス（ｉｓａｍｉｄｏｆｏｓ）、イソカルボホス（ｉｓｏｃａｒｂｏｐｈｏｓ）、イソキサチオン（ｉｓｏｘａｔｈｉｏｎ）、イソシクロセラム（ｉｓｏｃｙｃｌｏｓｅｒａｍ）、イソフェンホス・メチル（ｉｓｏｆｅｎｐｈｏｓ－ｍｅｔｈｙｌ）、イソプロカルブ（ｉｓｏｐｒｏｃａｒｂ）、イプシロン－メトフルトリン（ｅｐｓｉｌｏｎ－ｍｅｔｏｆｌｕｔｈｒｉｎ）、イプシロン－モムフルオロスリン（ｅｐｓｉｌｏｎ－ｍｏｍｆｌｕｏｒｏｔｈｒｉｎ）、イベルメクチン（ｉｖｅｒｍｅｃｔｉｎ）、イミシアホス（ｉｍｉｃｙａｆｏｓ）、イミダクロプリド（ｉｍｉｄａｃｌｏｐｒｉｄ）、イミプロトリン（ｉｍｉｐｒｏｔｈｒｉｎ）、インドキサカルブ（ｉｎｄｏｘａｃａｒｂ）、エスフェンバレレート（ｅｓｆｅｎｖａｌｅｒａｔｅ）、エチオフェンカルブ（ｅｔｈｉｏｆｅｎｃａｒｂ）、エチオン（ｅｔｈｉｏｎ）、エチプロール（ｅｔｈｉｐｒｏｌｅ）、エチレンジブロミド（ｅｔｈｙｌｅｎｅ　ｄｉｂｒｏｍｉｄｅ）、エトキサゾール（ｅｔｏｘａｚｏｌｅ）、エトフェンプロックス（ｅｔｏｆｅｎｐｒｏｘ）、エトプロホス（ｅｔｈｏｐｒｏｐｈｏｓ）、エトリムホス（ｅｔｒｉｍｆｏｓ）、エマメクチン（ｅｍａｍｅｃｔｉｎ）、エマメクチンベンゾエート（ｅｍａｍｅｃｔｉｎ　ｂｅｎｚｏａｔｅ）、エンドスルファン（ｅｎｄｏｓｕｌｆａｎ）、エンペントリン（ｅｍｐｅｎｔｈｒｉｎ）、オキサゾスルフィル（ｏｘａｚｏｓｕｌｆｙｌ）、オキサミル（ｏｘａｍｙｌ）、オキシジメトン・メチル（ｏｘｙｄｅｍｅｔｏｎ－ｍｅｔｈｙｌ）、オキシデプロホス（ｏｘｙｄｅｐｒｏｆｏｓ）、オメトエート（ｏｍｅｔｈｏａｔｅ）、カズサホス（ｃａｄｕｓａｆｏｓ）、カッパ－テフルトリン（ｋａｐｐａ－ｔｅｆｌｕｔｈｒｉｎ）、カッパ－ビフェントリン（ｋａｐｐａ－ｂｉｆｅｎｔｈｒｉｎ）、カランジン（ｋａｒａｎｊｉｎ）、カルタップ（ｃａｒｔａｐ）、カルバリル（ｃａｒｂａｒｙｌ）、カルボスルファン（ｃａｒｂｏｓｕｌｆａｎ）、カルボフラン（ｃａｒｂｏｆｕｒａｎ）、ガンマ－ＢＨＣ（ｇａｍｍａ－ＢＨＣ）、キシリルカルブ（ｘｙｌｙｌｃａｒｂ）、キナルホス（ｑｕｉｎａｌｐｈｏｓ）、キノプレン（ｋｉｎｏｐｒｅｎｅ）、キノメチオネート（ｃｈｉｎｏｍｅｔｈｉｏｎａｔ）、クマホス（ｃｏｕｍａｐｈｏｓ）、クリオライト（ｃｒｙｏｌｉｔｅ）、クロチアニジン（ｃｌｏｔｈｉａｎｉｄｉｎ）、クロフェンテジン（ｃｌｏｆｅｎｔｅｚｉｎｅ）、クロマフェノジド（ｃｈｒｏｍａｆｅｎｏｚｉｄｅ）、クロラントラニリプロール（ｃｈｌｏｒａｎｔｒａｎｉｌｉｐｒｏｌｅ）、クロルエトキシホス（ｃｈｌｏｒｅｔｈｏｘｙｆｏｓ）、クロルデン（ｃｈｌｏｒｄａｎｅ）、クロルピクリン（ｃｈｌｏｒｏｐｉｃｒｉｎ）、クロルピリホス（ｃｈｌｏｒｐｙｒｉｆｏｓ）、クロルピリホス・メチル（ｃｈｌｏｒｐｙｒｉｆｏｓ－ｍｅｔｈｙｌ）、クロルフェナピル（ｃｈｌｏｒｆｅｎａｐｙｒ）、クロルフェンビンホス（ｃｈｌｏｒｆｅｎｖｉｎｐｈｏｓ）、クロルフルアズロン（ｃｈｌｏｒｆｌｕａｚｕｒｏｎ）、クロルメホス（ｃｈｌｏｒｍｅｐｈｏｓ）、クロロプラレスリン（ｃｈｌｏｒｏｐｒａｌｌｅｔｈｒｉｎ）、シアジピル（ｃｙａｚｙｐｙｒ）、シアノホス（ｃｙａｎｏｐｈｏｓ）、ジアフェンチウロン（ｄｉａｆｅｎｔｈｉｕｒｏｎ）、ジアミダホス（ｄｉａｍｉｄａｆｏｓ）、シアントラニリプロール（ｃｙａｎｔｒａｎｉｌｉｐｒｏｌｅ）、ジエノクロル（ｄｉｅｎｏｃｈｌｏｒ）、シエノピラフェン（ｃｙｅｎｏｐｙｒａｆｅｎ）、ジオキサベンゾホス（ｄｉｏｘａｂｅｎｚｏｆｏｓ）、ジオフェノラン（ｄｉｏｆｅｎｏｌａｎ）、シクラニリプロール（ｃｙｃｌａｎｉｌｉｐｒｏｌｅ）、シクロキサプリド（ｃｙｃｌｏｘａｐｒｉｄ）、ジクロトホス（ｄｉｃｒｏｔｏｐｈｏｓ）、ジクロフェンチオン（ｄｉｃｈｌｏｆｅｎｔｈｉｏｎ）、シクロプロトリン（ｃｙｃｌｏｐｒｏｔｈｒｉｎ）、ジクロルボス（ｄｉｃｈｌｏｒｖｏｓ）、ジクロロメゾチアズ（ｄｉｃｌｏｒｏｍｅｚｏｔｉａｚ）、ジコホル（ｄｉｃｏｆｏｌ）、ジシクラニル（ｄｉｃｙｃｌａｎｉｌ）、ジスルホトン（ｄｉｓｕｌｆｏｔｏｎ）、ジノテフラン（ｄｉｎｏｔｅｆｕｒａｎ）、ジノブトン（ｄｉｎｏｂｕｔｏｎ）、シハロジアミド（ｃｙｈａｌｏｄｉａｍｉｄｅ）、シハロトリン（ｃｙｈａｌｏｔｈｒｉｎ）［ｇａｍｍａ－体，ｌａｍｂｄａ－体を含む］、シフェノトリン（ｃｙｐｈｅｎｏｔｈｒｉｎ）［（１Ｒ）－ｔｒａｎｓ－体を含む］、シフルトリン（ｃｙｆｌｕｔｈｒｉｎ）［ｂｅｔａ－体を含む］、ジフルベンズロン（ｄｉｆｌｕｂｅｎｚｕｒｏｎ）、シフルメトフェン（ｃｙｆｌｕｍｅｔｏｆｅｎ）、ジフロビダジン（ｄｉｆｌｏｖｉｄａｚｉｎ）、シヘキサチン（ｃｙｈｅｘａｔｉｎ）、シペルメトリン（ｃｙｐｅｒｍｅｔｈｒｉｎ）［ａｌｐｈａ－体，ｂｅｔａ－体，ｔｈｅｔａ－体，ｚｅｔａ－体を含む］、ジムプロピリダッツ(ｄｉｍｐｒｏｐｙｒｉｄａｚ）、ジメチル－２，２，２－トリクロロ－１－ヒドロキシエチルホスホネート（ＤＥＰ）、ジメチルビンホス（ｄｉｍｅｔｈｙｌｖｉｎｐｈｏｓ）、ジメトエート（ｄｉｍｅｔｈｏａｔｅ）、ジメフルスリン（ｄｉｍｅｆｌｕｔｈｒｉｎ）、シラフルオフェン（ｓｉｌａｆｌｕｏｆｅｎ）、シロマジン（ｃｙｒｏｍａｚｉｎｅ）、スピネトラム（ｓｐｉｎｅｔｏｒａｍ）、スピノサド（ｓｐｉｎｏｓａｄ）、スピロジクロフェン（ｓｐｉｒｏｄｉｃｌｏｆｅｎ）、スピロテトラマト（ｓｐｉｒｏｔｅｔｒａｍａｔ）、スピロピジオン（ｓｐｉｒｏｐｉｄｉｏｎ）、スピロメシフェン（ｓｐｉｒｏｍｅｓｉｆｅｎ）、スルコフロン・ナトリウム塩（ｓｕｌｃｏｆｕｒｏｎ－ｓｏｄｉｕｍ）、スルフルラミド（ｓｕｌｆｌｕｒａｍｉｄ）、スルホキサフロル（ｓｕｌｆｏｘａｆｌｏｒ）、スルホテップ（ｓｕｌｆｏｔｅｐ）、ダイアジノン（ｄｉａｚｉｎｏｎ）、チアクロプリド（ｔｈｉａｃｌｏｐｒｉｄ）、チアメトキサム（ｔｈｉａｍｅｔｈｏｘａｍ）、チオキサザフェン（ｔｉｏｘａｚａｆｅｎ）、チオジカルブ（ｔｈｉｏｄｉｃａｒｂ）、チオシクラム（ｔｈｉｏｃｙｃｌａｍ）、チオスルタップ（ｔｈｉｏｓｕｌｔａｐ）、チオナジン（ｔｈｉｏｎａｚｉｎ）、チオファノックス（ｔｈｉｏｆａｎｏｘ）、チオメトン（ｔｈｉｏｍｅｔｏｎ）、チクロピラゾフロール（ｔｙｃｌｏｐｙｒａｚｏｆｌｏｒ）、テトラクロラントラニリプロール（ｔｅｔｒａｃｈｌｏｒａｎｔｒａｎｉｌｉｐｒｏｌｅ）、テトラクロルビンホス（ｔｅｔｒａｃｈｌｏｒｖｉｎｐｈｏｓ）、テトラジホン（ｔｅｔｒａｄｉｆｏｎ）、テトラニリプロール（ｔｅｔｒａｎｉｌｉｐｒｏｌｅ）、テトラメチルフルスリン（ｔｅｔｒａｍｅｔｈｙｌｆｌｕｔｈｒｉｎ）、テトラメトリン（ｔｅｔｒａｍｅｔｈｒｉｎ）、テブピリムホス（ｔｅｂｕｐｉｒｉｍｆｏｓ）、テブフェノジド（ｔｅｂｕｆｅｎｏｚｉｄｅ）、テブフェンピラド（ｔｅｂｕｆｅｎｐｙｒａｄ）、テフルトリン（ｔｅｆｌｕｔｈｒｉｎ）、テフルベンズロン（ｔｅｆｌｕｂｅｎｚｕｒｏｎ）、デメトン・Ｓ・メチル（ｄｅｍｅｔｏｎ－Ｓ－ｍｅｔｈｙｌ）、テメホス（ｔｅｍｅｐｈｏｓ）、デルタメトリン（ｄｅｌｔａｍｅｔｈｒｉｎ）、テルブホス（ｔｅｒｂｕｆｏｓ）、トラロメトリン（ｔｒａｌｏｍｅｔｈｒｉｎ）、トランスフルトリン（ｔｒａｎｓｆｌｕｔｈｒｉｎ）、トリアザメート（ｔｒｉａｚａｍａｔｅ）、トリアゾホス（ｔｒｉａｚｏｐｈｏｓ）、トリクロルホン（ｔｒｉｃｈｌｏｒｆｏｎ）、トリフルムロン（ｔｒｉｆｌｕｍｕｒｏｎ）、トリフルメゾピリム（ｔｒｉｆｌｕｍｅｚｏｐｙｒｉｍ）、トリメタカルブ（ｔｒｉｍｅｔｈａｃａｒｂ）、トルフェンピラド（ｔｏｌｆｅｎｐｙｒａｄ）、ナレッド（ｎａｌｅｄ）、ニコチン（ｎｉｃｏｔｉｎｅ）、ニテンピラム（ｎｉｔｅｎｐｙｒａｍ）、ネマデクチン（ｎｅｍａｄｅｃｔｉｎ）、ノバルロン（ｎｏｖａｌｕｒｏｎ）、ノビフルムロン（ｎｏｖｉｆｌｕｍｕｒｏｎ）、バーティシリウム　レカニ（Ｖｅｒｔｉｃｉｌｌｉｕｍ　ｌｅｃａｎｉｉ）、ハイドロプレン（ｈｙｄｒｏｐｒｅｎｅ）、バチルス ・アミロリケファシエンス （Ｂａｃｉｌｌｕｓ　ａｍｙｌｏｌｉｑｕｅｆａｃｉｅｎｓ）、バチルス・フィルムス（Ｂａｃｉｌｌｕｓ　ｆｉｒｍｕｓ）、バチルス・スフェリカス（Ｂａｃｉｌｌｕｓ　ｓｐｈａｅｒｉｃｕｓ）、バチルス・ズブチリス（Ｂａｃｉｌｌｕｓ　ｓｕｂｔｉｌｌｉｓ）、バチルス・チューリンゲンシス（Ｂａｃｉｌｌｕｓ　ｔｈｕｒｉｎｇｉｅｎｓｉｓ）、バチルス・チューリンゲンシス（Ｂａｃｉｌｌｕｓ　ｔｈｕｒｉｎｇｉｅｎｓｉｓ）の生産する昆虫毒素、バチルス・チューリンゲンシス・亜種・アイザワイ（Ｂａｃｉｌｌｕｓ　ｔｈｕｒｉｎｇｉｅｎｓｉｓ　ｓｕｂｓｐ．　Ａｉｚａｗａｉ）、バチルス・チューリンゲンシス・亜種・イスラエレンシス（Ｂａｃｉｌｌｕｓ　ｔｈｕｒｉｎｇｉｅｎｓｉｓ　ｓｕｂｓｐ．　Ｉｓｒａｅｌｅｎｓｉｓ）、バチルス・チューリンゲンシス・亜種・クルスターキ（Ｂａｃｉｌｌｕｓ　ｔｈｕｒｉｎｇｉｅｎｓｉｓ　ｓｕｂｓｐ．　Ｋｕｒｓｔａｋｉ）、バチルス・チューリンゲンシス・亜種・テネブリオニス（Ｂａｃｉｌｌｕｓ　ｔｈｕｒｉｎｇｉｅｎｓｉｓ　ｓｕｂｓｐ．　Ｔｅｎｅｂｒｉｏｎｉｓ）、バチルス・ポピリエ（Ｂａｃｉｌｌｕｓ　ｐｏｐｉｌｌｉａｅ）、パスツーリアペネトランス胞子（Ｐａｓｔｅｕｒｉａｐｅｎｅｔｒａｎｓ）、バミドチオン（ｖａｍｉｄｏｔｈｉｏｎ）、パラチオン（ｐａｒａｔｈｉｏｎ）、パラチオン・メチル（ｐａｒａｔｈｉｏｎ－ｍｅｔｈｙｌ）、ハルフェンプロックス（ｈａｌｆｅｎｐｒｏｘ）、ハロフェノジド（ｈａｌｏｆｅｎｏｚｉｄｅ）、ビオアレスリン（ｂｉｏａｌｌｅｔｈｒｉｎ）、ビオアレスリンＳ‐シクロペンテニル（ｂｉｏａｌｌｅｔｈｒｉｎ　Ｓ－ｃｙｃｌｏｐｅｎｔｅｎｙｌ）、ビオレスメトリン（ｂｉｏｒｅｓｍｅｔｈｒｉｎ）、ビス－（２－クロロ－１－メチルエチル）エーテル（ＤＣＩＰ）、ビストリフルロン（ｂｉｓｔｒｉｆｌｕｒｏｎ）、ヒドラメチルノン（ｈｙｄｒａｍｅｔｈｙｌｎｏｎ）、ビフェナゼート（ｂｉｆｅｎａｚａｔｅ）、ビフェントリン（ｂｉｆｅｎｔｈｒｉｎ）、ピフルブミド（ｐｙｆｌｕｂｕｍｉｄｅ）、ピペロニルブトキシド（ｐｉｐｅｒｏｎｙｌ　ｂｕｔｏｘｉｄｅ）、ピメトロジン（ｐｙｍｅｔｒｏｚｉｎｅ）、ピラクロホス（ｐｙｒａｃｌｏｆｏｓ）、ピラフルプロール（ｐｙｒａｆｌｕｐｒｏｌｅ）、ピリダフェンチオン（ｐｙｒｉｄａｐｈｅｎｔｈｉｏｎ）、ピリダベン（ｐｙｒｉｄａｂｅｎ）、ピリダリル（ｐｙｒｉｄａｌｙｌ）、ピリフルキナゾン（ｐｙｒｉｆｌｕｑｕｉｎａｚｏｎ）、ピリプロール（ｐｙｒｉｐｒｏｌｅ）、ピリプロキシフェン（ｐｙｒｉｐｒｏｘｙｆｅｎ）、ピリミカルブ（ｐｉｒｉｍｉｃａｒｂ）、ピリミジフェン（ｐｙｒｉｍｉｄｉｆｅｎ）、ピリミノストロビン（ｐｙｒｉｍｉｎｏｓｔｒｏｂｉｎ）、ピリミホス・メチル（ｐｉｒｉｍｉｐｈｏｓ－ｍｅｔｈｙｌ）、ピレトリン（ｐｙｒｅｔｈｒｉｎｅ）、ファムフル（ｆａｍｐｈｕｒ）、フィプロニル（ｆｉｐ
ｒｏｎｉｌ）、フェナザキン（ｆｅｎａｚａｑｕｉｎ）、フェナミホス（ｆｅｎａｍｉｐｈｏｓ）、フェニトロチオン（ｆｅｎｉｔｒｏｔｈｉｏｎ）、フェノキシカルブ（ｆｅｎｏｘｙｃａｒｂ）、フェノチオカルブ（ｆｅｎｏｔｈｉｏｃａｒｂ）、フェノトリン（ｐｈｅｎｏｔｈｒｉｎ）［（１Ｒ）－ｔｒａｎｓ－体を含む］、フェノブカルブ（ｆｅｎｏｂｕｃａｒｂ）、フェンチオン（ｆｅｎｔｈｉｏｎ）、フェントエート（ｐｈｅｎｔｈｏａｔｅ）、フェンバレレート（ｆｅｎｖａｌｅｒａｔｅ）、フェンピロキシメート（ｆｅｎｐｙｒｏｘｉｍａｔｅ）、フェンブタンチン・オキシド（ｆｅｎｂｕｔａｔｉｎ　ｏｘｉｄｅ）、フェンプロパトリン（ｆｅｎｐｒｏｐａｔｈｒｉｎ）、フォノホス（ｆｏｎｏｆｏｓ）、フッ化スルフリル（ｓｕｌｆｕｒｙｌ　ｆｌｕｏｒｉｄｅ）、ブトカルボキシム（ｂｕｔｏｃａｒｂｏｘｉｍ）、ブトキシカルボキシム（ｂｕｔｏｘｙｃａｒｂｏｘｉｍ）、ブプロフェジン（ｂｕｐｒｏｆｅｚｉｎ）、フラチオカルブ（ｆｕｒａｔｈｉｏｃａｒｂ）、プラレトリン（ｐｒａｌｌｅｔｈｒｉｎ）、フルアクリピリム（ｆｌｕａｃｒｙｐｙｒｉｍ）、フルアザインドリジン（ｆｌｕａｚａｉｎｄｏｌｉｚｉｎｅ）、フルアズロン（ｆｌｕａｚｕｒｏｎ）、フルエンスルホン（ｆｌｕｅｎｓｕｌｆｏｎｅ）、フルオピラム（ｆｌｕｏｐｙｒａｍ）、フルオロ酢酸ナトリウム塩（ｓｏｄｉｕｍ　ｆｌｕｏｒｏａｃｅｔａｔｅ）、フルキサメタミド（ｆｌｕｘａｍｅｔａｍｉｄｅ）、フルシクロクスロン（ｆｌｕｃｙｃｌｏｘｕｒｏｎ）、フルシトリネート（ｆｌｕｃｙｔｈｒｉｎａｔｅ）、フルスルファミド（ｆｌｕｓｕｌｆａｍｉｄｅ）、フルトリン（ｆｌｕｔｈｒｉｎ）、フルバリネート（ｆｌｕｖａｌｉｎａｔｅ）　［ｔａｕ－体を含む］、フルピラジフロン（ｆｌｕｐｙｒａｄｉｆｕｒｏｎｅ）、フルピラゾホス（ｆｌｕｐｙｒａｚｏｆｏｓ）、フルピリミン（ｆｌｕｐｙｒｉｍｉｎ）、フルフィプロール（ｆｌｕｆｉｐｒｏｌｅ）、フルフェネリム（ｆｌｕｆｅｎｅｒｉｍ）、フルフェノキシストロビン（ｆｌｕｆｅｎｏｘｙｓｔｒｏｂｉｎ）、フルフェノクスロン（ｆｌｕｆｅｎｏｘｕｒｏｎ）、フルヘキサフォン（ｆｌｕｈｅｘａｆｏｎ）、フルベンジアミド（ｆｌｕｂｅｎｄｉａｍｉｄｅ）、フルメトリン（ｆｌｕｍｅｔｈｒｉｎ）、フルララナル（ｆｌｕｒａｌａｎｅｒ）、フルリムフェン（ｆｌｕｒｉｍｆｅｎ）、ジャスモン（ｊａｓｍｏｎｅ）、シス－ジャスモン（ｃｉｓ－ｊａｓｍｏｎｅ）、プロチオホス（ｐｒｏｔｈｉｏｆｏｓ）、プロトリフェンブト（ｐｒｏｔｒｉｆｅｎｂｕｔｅ）、フロニカミド（ｆｌｏｎｉｃａｍｉｄ）、プロパホス（ｐｒｏｐａｐｈｏｓ）、プロパルギット（ｐｒｏｐａｒｇｉｔｅ）、プロフェノホス（ｐｒｏｆｅｎｏｆｏｓ）、ブロフラニリド（ｂｒｏｆｌａｎｉｌｉｄｅ）、プロフルトリン（ｐｒｏｆｌｕｔｈｒｉｎ）、プロペタムホス（ｐｒｏｐｅｔａｍｐｈｏｓ）、プロポキスル（ｐｒｏｐｏｘｕｒ）、フロメトキン（ｆｌｏｍｅｔｏｑｕｉｎ）、ブロモプロピレート（ｂｒｏｍｏｐｒｏｐｙｌａｔｅ）、ヘキサチアゾクス（ｈｅｘｙｔｈｉａｚｏｘ）、ヘキサフルムロン（ｈｅｘａｆｌｕｍｕｒｏｎ）、ペキロマイセス・テヌイペス（Ｐａｃｉｌｉｍｙｃｅｓ　ｔｅｎｕｉｐｅｓ）、ペキロマイセス・フモソロセウス（Ｐａｅｃｉｌｏｍｙｃｅｓ　ｆｕｍｏｓｏｒｏｃｅｕｓ）、ペキロマイセス・リラキナス（Ｐａｅｃｉｌｏｍｙｃｅｓ　ｌｉｌａｃｉｎｕｓ）、ヘプタフルスリン（ｈｅｐｔａｆｌｕｔｈｒｉｎ）、ヘプテノホス（ｈｅｐｔｅｎｏｐｈｏｓ）、ペルメトリン（ｐｅｒｍｅｔｈｒｉｎ）、ベンクロチアズ（ｂｅｎｃｌｏｔｈｉａｚ）、ベンズピリモキサン（ｂｅｎｚｐｙｒｉｍｏｘａｎ）、ベンスルタップ（ｂｅｎｓｕｌｔａｐ）、ベンゾキシメート（ｂｅｎｚｏｘｉｍａｔｅ）、ベンダイオカルブ（ｂｅｎｄｉｏｃａｒｂ）、ベンフラカルブ（ｂｅｎｆｕｒａｃａｒｂ）、ボーベリア・テネーラ（Ｂｅａｕｖｅｒｉａ　ｔｅｎｅｌｌａ）、ボーベリア・バッシアーナ（Ｂｅａｕｖｅｒｉａ　ｂａｓｓｉａｎａ）、ボーベリア・ブロンニアティ（Ｂｅａｕｖｅｒｉａ　ｂｒｏｎｇｎｉａｒｔｉｉ）、ホキシム（ｐｈｏｘｉｍ）、ホサロン（ｐｈｏｓａｌｏｎｅ）、ホスチアゼート（ｆｏｓｔｈｉａｚａｔｅ）、ホスチエタン（ｆｏｓｔｈｉｅｔａｎ）、ホスファミドン（ｐｈｏｓｐｈａｍｉｄｏｎ）、ホスメット（ｐｈｏｓｍｅｔ）、ポリナクチン複合体（ｐｏｌｙｎａｃｔｉｎｓ）、ホルメタネート（ｆｏｒｍｅｔａｎａｔｅ）、ホレート（ｐｈｏｒａｔｅ）、マシン油（ｍａｃｈｉｎｅ　ｏｉｌ）、マラチオン（ｍａｌａｔｈｉｏｎ）、ミルベメクチン（ｍｉｌｂｅｍｅｃｔｉｎ）、メカルバム（ｍｅｃａｒｂａｍ）、メスルフェンホス（ｍｅｓｕｌｆｅｎｆｏｓ）、メソミル（ｍｅｔｈｏｍｙｌ）、メタアルデヒド（ｍｅｔａｌｄｅｈｙｄｅ）、メタフルミゾン（ｍｅｔａｆｌｕｍｉｚｏｎｅ）、メタミドホス（ｍｅｔｈａｍｉｄｏｐｈｏｓ）、メタム（ｍｅｔｈａｍ）、メチオカルブ（ｍｅｔｈｉｏｃａｒｂ）、メチダチオン（ｍｅｔｈｉｄａｔｈｉｏｎ）、メチルイソチオシアネート（ｍｅｔｈｙｌ　ｉｓｏｔｈｉｏｃｙａｎａｔｅ）、メチルブロマイド（ｍｅｔｈｙｌ　ｂｒｏｍｉｄｅ）、メトキシクロル（ｍｅｔｈｏｘｙｃｈｌｏｒ）、メトキシフェノジド（ｍｅｔｈｏｘｙｆｅｎｏｚｉｄｅ）、メトトリン（ｍｅｔｈｏｔｈｒｉｎ）、メトフルトリン（ｍｅｔｏｆｌｕｔｈｒｉｎ）、メトプレン（ｍｅｔｈｏｐｒｅｎｅ）、メトルカルブ（ｍｅｔｏｌｃａｒｂ）、メビンホス（ｍｅｖｉｎｐｈｏｓ）、メペルフルスリン（ｍｅｐｅｒｆｌｕｔｈｒｉｎ）、モナクロスポリウム・フィマトパガム（Ｍｏｎａｃｒｏｓｐｏｒｉｕｍ　ｐｈｙｍａｔｏｐｈａｇｕｍ）、モノクロトホス（ｍｏｎｏｃｒｏｔｏｐｈｏｓ）、モムフルオロスリン（ｍｏｍｆｌｕｏｒｏｔｈｒｉｎ）、トリコデルマ・ハルチアナム（Ｔｒｉｃｈｏｄｅｒｍａ　ｈａｒｚｉａｎｕｍ）、リトルアＡ（ｌｉｔｌｕｒｅ－Ａ）、リトルアＢ（ｌｉｔｌｕｒｅ－Ｂ）、りん化アルミニウム（ａｌｕｍｉｎｉｕｍ　ｐｈｏｓｐｈｉｄｅ）、りん化亜鉛（ｚｉｎｃ　ｐｈｏｓｐｈｉｄｅ）、りん化水素（ｐｈｏｓｐｈｉｎｅ）、ルフェヌロン（ｌｕｆｅｎｕｒｏｎ）、レスカルレ（ｒｅｓｃａｌｕｒｅ）、レスメトリン（ｒｅｓｍｅｔｈｒｉｎ）、レピメクチン（ｌｅｐｉｍｅｃｔｉｎ）、ロテノン（ｒｏｔｅｎｏｎｅ）、核多角体病ウイルス包埋体、酸化フェンブタスズ（ｆｅｎｂｕｔａｔｉｎ　ｏｘｉｄｅ）、石灰窒素（ｃａｌｃｉｕｍ　ｃｙａｎｉｄｅ）、有機スズ化合物（ｏｒｇａｎｏｔｉｎｓ）、硫酸ニコチン（ｎｉｃｏｔｉｎｅ－ｓｕｌｆａｔｅ）、（Ｚ）－１１－テトラデセニル＝アセタート、（Ｚ）－１１－ヘキサデセナール、（Ｚ）－１１－ヘキサデセニル＝アセタート、（Ｚ）－９，１２－テトラデカジエニル＝アセタート、（Ｚ）－９－テトラデセン－１－オール、（Ｚ，Ｅ）－９，１１－テトラデカジエニル＝アセタート、（Ｚ，Ｅ）－９，１２－テトラデカジエニル＝アセタート、１，１，１－トリクロロ－２，２－ビス（４－クロロフェニル）エタン（ＤＤＴ）、１，３‐ジクロロプロペン（１，３－ｄｉｃｈｌｏｒｏｐｒｏｐｅｎｅ）、２－クロロ－４－フルオロ-５-［（５－トリフルオロメチルチオ）ペンチルオキシ］フェニル ２，２，２－トリフルオロエチル スルホキシド（化学名、ＣＡＳ登録番号：１４７２０５０－０４－６）、２，４－ジクロロ－５－｛２－［４－（トリフルオロメチル）フェニル］エトキシ｝フェニル ２，２，２－トリフルオロエチル スルホキシド（化学名、ＣＡＳ登録番号：１４７２０５２－１１－１）、２，４－ジメチル－５－［６－（トリフルオロメチルチオ）へキシルオキシ］フェニル－２，２，２－トリフルオロエチル スルホキシド（化学名、ＣＡＳ登録番号：１４７２０５０－３４－２）、２－｛２－フルオロ－４‐メチル－５－［（２，２，２－トリフルオロエチル）スルフィニル］フェノキシ｝－５－（トリフルオロメチル）ピリジン（化学名、ＣＡＳ登録番号：１４４８７５８－６２－０）、３－クロロ－２－｛２－フルオロ－４‐メチル－５－［（２，２，２－トリフルオロエチル）スルフィニル］フェノキシ｝－５－（トリフルオロメチル）ピリジン（化学名、ＣＡＳ登録番号：１４４８７６１－２８－１）、４，６－ジニトロ－ｏ－クレゾール（ＤＮＯＣ）、４－フルオロ－２－メチル－５－（５，５－ジメチルヘキシルオキシ］フェニル ２，２，２－トリフルオロエチル スルホキシド（化学名、ＣＡＳ登録番号：１４７２０４７－７１－４）、Ｂｔタンパク質　（Ｃｒｙ１Ａｂ，　Ｃｒｙ１Ａｃ，　Ｃｒｙ１Ｆａ，　Ｃｒｙ２Ａｂ，　ｍＣｒｙ３Ａ，　Ｃｒｙ３Ａｂ，　Ｃｒｙ３Ｂｂ，　Ｃｒｙ３４／３５Ａｂ１）、ＣＬ９００１６７（コード番号）、ＮＡ－８５（コード番号）、ＮＩ－３０（コード番号）、Ｏ，Ｏ－ジエチル－Ｏ－［４－（ジメチルスルファモイル）フェニル］－ホスホロチオネート（ＤＳＰ）、Ｏ－エチル－Ｏ－４－（ニトロフェニル）フェニルホスホノチオエート （ＥＰＮ）、ＲＵ１５５２５（コード番号）、ＸＭＣ（ＸＭＣ）、Ｚ－１３－イコセン－１０－オン、ＺＸＩ８９０１（コード番号）、Ｆ４２６０（コード番号）。 Insecticidal active ingredients:
Acrinathrin, azadirachtin, azamethiphos, acinonapyr, azinphos-acetyl, azinphos-acetyl, azinphos-acetyl, azinphos-acetyl, azinphos-acetate (Acetoprole), acephate, azocyclotin, abamectin, afidopyropen, afoxolaner, amideflumetrametrametrametrametamu , Alanycarb, aldicarb, aldoxycarb, allethrin [including d-cis-trans-form, d-trans-form], isazophos, isamiphos (isomidphos) Isocarbobophos, isoxathion, isocycloseram, isofenphos-methyl, isoprocarb, epsilon-methosulfon, epsilon-methofrurin, epsilon-methofrurin (epsilon-methoflurthrin). ,I Lumectin, imiciafos, imidacloprid, imiprothrin, indoxacarb, indoxacarb, esfenvaleth, ethiophenocarb, ethiophenocarb ethifenfolate Ethylene dibromide, etoxazole, etofenprox, ethoprophos, ethofophos, etrimfos, emamectin, emamectin benzoate zoate, endosulfan, empenthrin, oxazosulfyl, oxamyl, oxamyl, oxydimetone-methyl, oxydeprotosate, oxydeprotos (fos) cadasufos, kappa-tefluthrin, kappa-bifenthrin, kappa-bifenthrin, karanjin, cartap, carbaryl, carbosulfan, carbosulfan, carbosulfan BHC (gamma (BHC), xylylcarb, quinalphos, quinoprene, quinomethionate, coumaphos, cryolite, clothianizine, clothianidine, clothianidine , Chlorantraniliprole, chloroethoxyfos, chlordane, chlorpicrin, chlorpyrifos, chlorpyrifos-methyl. methyl), chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chloropraresulin, sialopyrinopyrinopyrosine, sialopyrinopyrinopyrosine, and sialopyrinopyrinopyrosine, sialopyrinopyrocyranopyrinopyrosine, sialopyrinopyrinopyrophile, sialopyrinopyrinopyrinopyrinopyrinopyrinopyrinopyrinopyrinopyrinopyrinopyrnopyrophilin. (Diafenthiuron), diamidafos, cyanantraniliprole, dienochlor, cyenopyrafen, dioxabenfosion, dioxabenfosio fenofiolan, dioxabenfosio fenofion, dioxabenfosio fenofi foran Rolls (cyclolaniprole), cycloxapride (cycloxaprid), dicrotophos (dicrofenthion), cycloprothrin (cycloprothrin), dichlorvos (dichlorodizol), dichlorofoliz (dichlorzizozil) Disulfoton, dinotefuran, dinobuton, cyhalodiamide, cyhalothrin [including gamma- and lambda-forms], cifethothrin (Including 1R) -trans-form], cyfluthrin (including beta-form), diflubenzuron, diflubenzuron, cyflumetofen, difluvidazin, cyperthine, cyperthine, cyperthamine -, Beta-, theta- and zeta-forms], dimpropyridaz, dimethyl-2,2,2-trichloro-1-hydroxyethylphosphonate (DEP), dimethylvinphos ), Dimethoate, dimefluthrin, silafluofen (sil) fluofen, cyromazine, spinetoram, spinosad, spirodiclofen, spirotetrafonate, spirotropione, spiropision, spiropision, spiropision, spiropision -Sodium), sulfluramide, sulfoxaflor, sulfotep, sulfotep, diazinon, thiacloprid, thiamethoxam, thiamethoxam, thiamethoxam, thiamethoxam, thiamethoxam, thiamethoxam, thiamethoxam, thiamethoxam, thiamethoxam Thiodicarb, thiocyclam, thiosultap, thionazine, thiofanox, thiomethon, thiochloranilol, tyclopyrrazolol, tetraclopranolol Tetrachlorvinphos, tetradifon, tetraniliprol, tetramethylfluthrin, tetramethrin, tetramethrin, tebupirimphos Nozide (tebufenozide), tebufenpyrad (tebufenpyrad), tefluthrin (teflubenzuron), teflubenzuron (teflubenzuron), demeton-S-methyl (demethon-S-methyl, temefos (temefos), temefos (temefos), temefos (temefos) tralomethrin, transfluthrin, triazamate, triazophos, trichlorfon, triflumuron, triflumuron, triflumeriplimez, triflumetrime ethaccarb), tolfenpyrad, nared, nicotine, nicotine, nitenpyram, nemadectin, novaluron, novaluriculum, novifirumurinurium, novifirumurinurium, Noviflumurinurium C. hydroprene, Bacillus amyloliquefaciens, Bacillus filmus, Bacillus sphaeris, Bacillus subtilis bacillus. Ngenshisu (Bacillus thuringiensis), insect toxin produced by Bacillus thuringiensis (Bacillus thuringiensis), Bacillus thuringiensis, subsp. Aizawai (Bacillus thuringiensis subsp. Aizawai), Bacillus thuringiensis subsp. Israelensis, Bacillus thuringiensis subsp. Klestarki (Bacillus thuringiensis subsp. thuringiensis subsp. Tenebrionis, Bacillus popilliae, Pasteuria penetrance spores (Pasteuriapenetrans), vamidithion, parathion-methyl, parathion-parathion-methyl l), halfenprox, halofenozide, bioallethrin, bioallethrin S-cyclopentenyl (bioallethrin S-cyclopentenyl), bioresmethrin (2-chloro-methyl-bis-methyl-bis-methyl-bis-methyl-bis) ) Ether (DCIP), bistrifluron, hydramethylnon, bifenazate, bifenthrin, bifenthrin, piflubumide, piperonyl butyperoxide, piperonyl butyperoxide Pyroclofos, pyrafluprole, pyridafenthion, pyridaben, pyridaben, pyridalyl, pyrifluquinazone, pyriproxirim, pyriproxyl, pyripropromipyri, pyriprofenpyripirpyripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripiripirupiripiripiripirupiripiripirupiripiripiripiripiripiripiripiripiripiripiripiripirupiripiripiripiryu (Pyrimidifen), pyriminostrobin, pyrimiphos-methyl, pyrethrin, pyrethrine, famfur, fipronil
ronil), fenazaquin, fenamiphos, fenitrothion, fenoxycarb, fenothiocarb, phenothiocarb, phenothrin-carbo-r-carb- (r-carbo-r-carbo-r-carbo-r-carbo-r-carbo-r-carbo-carbo-r-carbo-r-carbo-r-carbo-r-carbo-r-carbo-r-carbo-r-carbo-r-carbo-b) Fenthion, fenthoate, fenvalerate, fenpyroximate, fenbutatin oxide, fenpropatrin, fonoproponthrin, fonophosulfon, fonofosthrin sulfuryl fluoride), Butokarubokishimu (butocarboxim), butoxy carboxymethyl oxime (butoxycarboxim), buprofezin (buprofezin), furathiocarb (furathiocarb), prallethrin (prallethrin), fluacrypyrim (fluacrypyrim), full azaindolizine (fluazaindolizine), fluazuron (fluazuron) , Fluensulfone, fluopyram, sodium fluoroacetate, fluxamethamide, flucycloxuron, flucitrinate flucythrinate, flusulfamide, fluthrin, fluvalinate, including the tau-form, flupyradifurone, flupyrazofuramin, flupyrazoloflufurin, flupyramine flufenerim), flufenoxystrobin, flufenoxuron, fluhexafon, flubendiamide, flumethriner, flurathral, flurathral, flurathral, flurathral, flurathral Limufen, jasmon, jasmon, cis-jasmon, prothiofos, protrifenbute, flonicamid, propaphafos, propaphophos ), Brofuranilide, profluthrin, propetamphos, propoxur, propoxur, flomethoquin, bromopropylate, hexathiazox, hexathiazox, hexathiazox, thithiazox hexaflumuron), Pekiromaisesu tenuipes (Pacilimyces tenuipes), Pekiromaisesu-Fumosoroseusu (Paecilomyces fumosoroceus), Pekiromaisesu-Rirakinasu (Paecilomyces lilacinus), hepta full Surin (heptafluthrin), heptenophos (heptenophos), permethrin (permethrin), benclothiaz (benclothiaz), benz Benzpyrimoxan, bensultap, benzoximate, bendiocarb, benfuracarb, benfuracarb, beauveria tenera (B) auveria tenella, Beauveria bassiana, Beauveria brongniarti, phoxim, phosone, phosthiate, phosthiaz, phosiati, fosthiaz, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiati, phosiaz, Polynactins complex, formatenate, formate, machine oil, malathion, malbemectin, melbectin, mecarbamphosme ulfenfos, methomyl, methaldehyde, methflumizone, methamidophos, metham, methiocarb, methiothiothiomethyl, methiothiothiomethion, thiomethiothiothiomethyl methyl bromide, methoxychlor, methoxyfenozide, methotrin, methfluthrin, methoprene, methocarb, methocarb (Mevinphos), meperfluthrin (meperfluthrin), monacrosporium phymatopagum (Monocrosporium phymatophagum), monocrotophos (momonofluorosulin), momoflua mori torimu atromu rinotorima ruria humor tromuria thorima tori humor tromuria thoruma ri デ ル a マ Ｔ Ｔ ｍ Ｔ Ｔ ｚ ｍ ｍ. (Liture-B), aluminum phosphide (aluminium phosphide), zinc phosphide (zinc phosphide), hydrogen phosphide (phosphine), lufenuron (lufenuron), rescalure, resmethrin (resmethrin) epicinetin, rotenone, nuclear polyhedrosis virus embedding, fenbutatin oxide, calcium cyanide, organic tin compounds (organotins), nicotine sulfate (nicotine-sulphate), (nicotine-sulphate) 11-tetradecenyl acetate, (Z) -11-hexadecenal, (Z) -11-hexadecenyl acetate, (Z) -9,12-tetradecadienyl acetate, (Z) -9-tetradecen-1-ol , (Z, E) -9,11-tetradecadienyl acetate, (Z, E) -9,12-tetradecadienyl acetate, 1,1,1-trichloro-2,2-bis (4 -Chlorophenyl) ethane (DDT), 1,3-dic Lopropene (1,3-dichloropropene), 2-chloro-4-fluoro-5-[(5-trifluoromethylthio) pentyloxy] phenyl 2,2,2-trifluoroethyl sulfoxide (chemical name, CAS registration number: 1472050) -04-6), 2,4-dichloro-5- {2- [4- (trifluoromethyl) phenyl] ethoxy} phenyl 2,2,2-trifluoroethyl sulfoxide (chemical name, CAS registration number: 1472052) 11-1), 2,4-dimethyl-5- [6- (trifluoromethylthio) hexyloxy] phenyl-2,2,2-trifluoroethyl sulfoxide (chemical name, CAS registration number: 1472050-34-2) , 2- {2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl) Rufinyl] phenoxy} -5- (trifluoromethyl) pyridine (chemical name, CAS Registry Number: 14448758-62-2), 3-chloro-2- {2-fluoro-4-methyl-5-[(2,2 , 2-Trifluoroethyl) sulfinyl] phenoxy} -5- (trifluoromethyl) pyridine (chemical name, CAS registry number: 1448761-28-1), 4,6-dinitro-o-cresol (DNOC), 4- Fluoro-2-methyl-5- (5,5-dimethylhexyloxy) phenyl 2,2,2-trifluoroethyl sulfoxide (chemical name, CAS registry number: 1472047-71-4), Bt protein (Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35 b1), CL900167 (code number), NA-85 (code number), NI-30 (code number), O, O-diethyl-O- [4- (dimethylsulfamoyl) phenyl] -phosphorothionate ( DSP), O-ethyl-O-4- (nitrophenyl) phenylphosphonothioate (EPN), RU15525 (code number), XMC (XMC), Z-13-icosen-10-one, ZXI8901 (code number), F4260 (code number).
　次に、混合又は併用してもよい公知の殺菌剤又は病害防除剤化合物を例示する。 Next, known fungicidal or disease controlling compounds which may be mixed or used in combination are exemplified.
　殺菌活性成分：
　アザコナゾール（ａｚａｃｏｎａｚｏｌｅ）、アシベンゾラル・Ｓ・メチル（ａｃｉｂｅｎｚｏｌａｒ－Ｓ－ｍｅｔｈｙｌ）、アゾキシストロビン（ａｚｏｘｙｓｔｒｏｂｉｎ）、アニラジン（ａｎｉｌａｚｉｎｅ）、アミスルブロム（ａｍｉｓｕｌｂｒｏｍ）、アミノピリフェン（ａｍｉｎｏｐｙｒｉｆｅｎ）、アメトクトラジン（ａｍｅｔｏｃｔｒａｄｉｎ）、アルジモルフ（ａｌｄｉｍｏｒｐｈ）、イソチアニル（ｉｓｏｔｉａｎｉｌ）、イソピラザム（ｉｓｏｐｙｒａｚａｍ）、イソフェタミド（ｉｓｏｆｅｔａｍｉｄ）、イソフルシプラム（ｉｓｏｆｌｕｃｙｐｒａｍ）、イソプロチオラン（ｉｓｏｐｒｏｔｈｉｏｌａｎｅ）、イプコナゾール（ｉｐｃｏｎａｚｏｌｅ）、イプフルフェノキン（ｉｐｆｌｕｆｅｎｏｑｕｉｎ）、イプフェントリフルコナゾール（ｉｐｆｅｎｔｒｉｆｌｕｃｏｎａｚｏｌｅ）、イプロジオン（ｉｐｒｏｄｉｏｎｅ）、イプロバリカルブ（ｉｐｒｏｖａｌｉｃａｒｂ）、イプロベンホス（ｉｐｒｏｂｅｎｆｏｓ）、イマザリル（ｉｍａｚａｌｉｌ）、イミノクタジン・アルベシル酸塩（ｉｍｉｎｏｃｔａｄｉｎｅ－ａｌｂｅｓｉｌａｔｅ）、イミノクタジン酢酸塩（ｉｍｉｎｏｃｔａｄｉｎｅ－　ｔｒｉａｃｅｔａｔｅ）、イミベンコナゾール（ｉｍｉｂｅｎｃｏｎａｚｏｌｅ）、インピルフルキサム（ｉｎｐｙｒｆｌｕｘａｍ）、インプリマチンＡ（ｉｍｐｒｉｍａｔｉｎ　Ａ）、インプリマチンＢ（ｉｍｐｒｉｍａｔｉｎ　Ｂ）、エジフェンホス（ｅｄｉｆｅｎｐｈｏｓ）、エタコナゾ－ル（ｅｔａｃｏｎａｚｏｌｅ）、エタボキサム（ｅｔｈａｂｏｘａｍ）、エチリモル（ｅｔｈｉｒｉｍｏｌ）、エトキシキン（ｅｔｈｏｘｙｑｕｉｎ）、エトリジアゾール（ｅｔｒｉｄｉａｚｏｌｅ）、エネストロブリン（ｅｎｅｓｔｒｏｂｕｒｉｎ）、エノキサストロビン（ｅｎｏｘａｓｔｒｏｂｉｎ）、エポキシコナゾール（ｅｐｏｘｉｃｏｎａｚｏｌｅ）、オーガニックオイル（ｏｒｇａｎｉｃ　ｏｉｌｓ）、オキサジキシル（ｏｘａｄｉｘｙｌ）、オキサジニラゾール（ｏｘａｚｉｎｙｌａｚｏｌｅ）、オキサチアピプロリン（ｏｘａｔｈｉａｐｉｐｒｏｌｉｎ）、オキシカルボキシン（ｏｘｙｃａｒｂｏｘｉｎ）、オキシキノリン銅（ｏｘｉｎｅ－ｃｏｐｐｅｒ）、オキシテトラサイクリン（ｏｘｙｔｅｔｒａｃｙｃｌｉｎｅ）、オキスポコナゾールフマル酸塩（ｏｘｐｏｃｏｎａｚｏｌｅ－ｆｕｍａｒａｔｅ）、オキソリニック酸（ｏｘｏｌｉｎｉｃ　ａｃｉｄ）、オクタン酸銅（ｃｏｐｐｅｒ　ｄｉｏｃｔａｎｏａｔｅ）、オクチリノン（ｏｃｔｈｉｌｉｎｏｎｅ）、オフラセ（ｏｆｕｒａｃｅ）、オリサストロビン（ｏｒｙｓａｓｔｒｏｂｉｎ）、オルソフェニルフェノール（ｏ－ｐｈｅｎｙｌｐｈｅｎｏｌ）、カスガマイシン（ｋａｓｕｇａｍｙｃｉｎ）、カプタホール（ｃａｐｔａｆｏｌ）、カルプロパミド（ｃａｒｐｒｏｐａｍｉｄ）、カルベンダジム（ｃａｒｂｅｎｄａｚｉｍ）、カルボキシン（ｃａｒｂｏｘｉｎ）、カルボネ（ｃａｒｖｏｎｅ）、キノキシフェン（ｑｕｉｎｏｘｙｆｅｎ）、キノフメリン（ｑｕｉｎｏｆｕｍｅｌｉｎ）、キノメチオネート（ｃｈｉｎｏｍｅｔｈｉｏｎａｔ）、キャプタン（ｃａｐｔａｎ）、キンコナゾール（ｑｕｉｎｃｏｎａｚｏｌｅ）、キントゼン（ｑｕｉｎｔｏｚｅｎｅ）、グアザチン（ｇｕａｚａｔｉｎｅ）、クフラネブ（ｃｕｆｒａｎｅｂ）、クメトキシストロビン（ｃｏｕｍｅｔｈｏｘｙｓｔｒｏｂｉｎ）、クモキシストロビン（ｃｏｕｍｏｘｙｓｔｒｏｂｉｎ）、クレソキシム・メチル（ｋｒｅｓｏｘｉｍ－ｍｅｔｈｙｌ）、クロジラコン（ｃｌｏｚｙｌａｃｏｎ）、クロゾリネート（ｃｈｌｏｚｏｌｉｎａｔｅ）、クロロタロニル（ｃｈｌｏｒｏｔｈａｌｏｎｉｌ）、クロロネブ（ｃｈｌｏｒｏｎｅｂ）、シアゾファミド（ｃｙａｚｏｆａｍｉｄ）、ジエトフェンカルブ（ｄｉｅｔｈｏｆｅｎｃａｒｂ）、ジクロシメット（ｄｉｃｌｏｃｙｍｅｔ）、ジクロフルアニド（ｄｉｃｈｌｏｆｌｕａｎｉｄ）、ジクロベンチアゾクス（ｄｉｃｈｌｏｂｅｎｔｉａｚｏｘ）、ジクロメジン（ｄｉｃｌｏｍｅｚｉｎｅ）、ジクロラン（ｄｉｃｌｏｒａｎ）、ジクロロフェン（ｄｉｃｈｌｏｒｏｐｈｅｎ）、ジチアノン（ｄｉｔｈｉａｎｏｎ）、ジニコナゾール（ｄｉｎｉｃｏｎａｚｏｌｅ）、ジニコナゾール・Ｍ（ｄｉｎｉｃｏｎａｚｏｌｅ－Ｍ）、ジネブ（ｚｉｎｅｂ）、ジノカップ（ｄｉｎｏｃａｐ）、ジピメチトロン（ｄｉｐｙｍｅｔｉｔｒｏｎｅ）、ジフェニルアミン（ｄｉｐｈｅｎｙｌａｍｉｎｅ）、ジフェノコナゾール（ｄｉｆｅｎｏｃｏｎａｚｏｌｅ）、シフルフェナミド（ｃｙｆｌｕｆｅｎａｍｉｄ）、ジフルメトリム（ｄｉｆｌｕｍｅｔｏｒｉｍ）、シプロコナゾール（ｃｙｐｒｏｃｏｎａｚｏｌｅ）、シプロジニル（ｃｙｐｒｏｄｉｎｉｌ）、シメコナゾール（ｓｉｍｅｃｏｎａｚｏｌｅ）、ジメチリモル（ｄｉｍｅｔｈｉｒｉｍｏｌ）、ジメチルジスルフィド（ｄｉｍｅｔｈｙｌ　ｄｉｓｕｌｆｉｄｅ）、ジメトモルフ（ｄｉｍｅｔｈｏｍｏｒｐｈ）、シモキサニル（ｃｙｍｏｘａｎｉｌ）、ジモキシストロビン（ｄｉｍｏｘｙｓｔｒｏｂｉｎ）、シュードモナス・ロデシア・ＨＡＩ－０８０４（Ｐｓｅｕｄｏｍｏｎａｓ　ｒｈｏｄｅｓｉａｅ　ＨＡＩ－０８０４）、ジラム（ｚｉｒａｍ）、シルチオファム（ｓｉｌｔｈｉｏｆａｍ）、ストレプトマイシン（ｓｔｒｅｐｔｏｍｙｃｉｎ）、スピロキサミン（ｓｐｉｒｏｘａｍｉｎｅ）、セダキサン（ｓｅｄａｘａｎｅ）、ゾキサミド（ｚｏｘａｍｉｄｅ）、ソラテノール（ｓｏｌａｔｅｎｏｌ）、ダゾメット（ｄａｚｏｍｅｔ）、タラロマイセス　フラバス（Ｔａｌａｒｏｍｙｃｅｓ　ｆｌａｖｕｓ）、チアジニル（ｔｉａｄｉｎｉｌ）、チアベンダゾール（ｔｈｉａｂｅｎｄａｚｏｌｅ）、チウラム（ｔｈｉｒａｍ）、チオファネート（ｔｈｉｏｐｈａｎａｔｅ）、チオファネート・メチル（ｔｈｉｏｐｈａｎａｔｅ－ｍｅｔｈｙｌ）、チフルザミド（ｔｈｉｆｌｕｚａｍｉｄｅ）、チラム（ｔｈｉｒａｍ）、テクナゼン（ｔｅｃｎａｚｅｎｅ）、テクロフタラム（ｔｅｃｌｏｆｔａｌａｍ）、テトラコナゾール（ｔｅｔｒａｃｏｎａｚｏｌｅ）、デバカルブ（ｄｅｂａｃａｒｂ）、テブコナゾール（ｔｅｂｕｃｏｎａｚｏｌｅ）、テブフロキン（ｔｅｂｕｆｌｏｑｕｉｎ）、テルビナフィン（ｔｅｒｂｉｎａｆｉｎｅ）、ドジン（ｄｏｄｉｎｅ）、ドデモルフ（ｄｏｄｅｍｏｒｐｈ）、トリアジメノール（ｔｒｉａｄｉｍｅｎｏｌ）、トリアジメホン（ｔｒｉａｄｉｍｅｆｏｎ）、トリアゾキシド（ｔｒｉａｚｏｘｉｄｅ）、トリクラミド（ｔｒｉｃｈｌａｍｉｄｅ）、トリクロピリカルブ（ｔｒｉｃｌｏｐｙｒｉｃａｒｂ）、トリコデルマ・アトロビリデ（Ｔｒｉｃｈｏｄｅｒｍａ　ａｔｒｏｖｉｒｉｄｅ）、トリシクラゾール（ｔｒｉｃｙｃｌａｚｏｌｅ）、トリチコナゾール（ｔｒｉｔｉｃｏｎａｚｏｌｅ）、トリデモルフ（ｔｒｉｄｅｍｏｒｐｈ）、トリフルミゾール（ｔｒｉｆｌｕｍｉｚｏｌｅ）、トリフロキシストロビン（ｔｒｉｆｌｏｘｙｓｔｒｏｂｉｎ）、トリホリン（ｔｒｉｆｏｒｉｎｅ）、トリルフルアニド（ｔｏｌｙｌｆｌｕａｎｉｄ）、トルクロホス・メチル（ｔｏｌｃｌｏｆｏｓ－ｍｅｔｈｙｌ）、トルニファニド（ｔｏｌｎｉｆａｎｉｄｅ）、トルプロカルブ（ｔｏｌｐｒｏｃａｒｂ）、ナーバム（ｎａｂａｍ）、ナタマイシン（ｎａｔａｍｙｃｉｎ）、ナフティフィン（ｎａｆｔｉｆｉｎｅ）、ニトラピリン（ｎｉｔｒａｐｙｒｉｎ）、ニトロタル・イソプロピル（ｎｉｔｒｏｔｈａｌ－ｉｓｏｐｒｏｐｙｌ）、ヌアリモル（ｎｕａｒｉｍｏｌ）、ノニルフェノールスルホン酸銅（ｃｏｐｐｅｒ　ｎｏｎｙｌ　ｐｈｅｎｏｌ　ｓｕｌｐｈｏｎａｔｅ）、バチルス・ズブチリス（Ｂａｃｉｌｌｕｓ　ｓｕｂｔｉｌｉｓ）（ｓｔｒａｉｎ：ＱＳＴ　７１３）、バリダマイシン（ｖａｌｉｄａｍｙｃｉｎ）、バリフェナレート（ｖａｌｉｆｅｎａｌａｔｅ）、ピカルブトラゾックス（ｐｉｃａｒｂｕｔｒａｚｏｘ）、ビキサフェン（ｂｉｘａｆｅｎ）、ピコキシストロビン（ｐｉｃｏｘｙｓｔｒｏｂｉｎ）、ピジフルメトフェン（ｐｙｄｉｆｌｕｍｅｔｏｆｅｎ）、ビテルタノール（ｂｉｔｅｒｔａｎｏｌ）、ビナパクリル（ｂｉｎａｐａｃｒｙｌ）、ヒノキチオール（ｈｉｎｏｋｉｔｉｏｌ）、ビフェニル（ｂｉｐｈｅｎｙｌ）、ピペラリン（ｐｉｐｅｒａｌｉｎ）、ヒメキサゾール（ｈｙｍｅｘａｚｏｌ）、ピラオキシストロビン（ｐｙｒａｏｘｙｓｔｒｏｂｉｎ）、ピラクロストロビン（ｐｙｒａｃｌｏｓｔｒｏｂｉｎ）、ピラジフルミド（ｐｙｒａｚｉｆｌｕｍｉｄ）、ピラゾホス（ｐｙｒａｚｏｐｈｏｓ）、ピラプロポイン（ｐｙｒａｐｒｏｐｏｙｎｅ）、ピラメトストロビン（ｐｙｒａｍｅｔｏｓｔｒｏｂｉｎ）、ピリオフェノン（ｐｙｒｉｏｆｅｎｏｎｅ）、ピリソキサゾール（ｐｙｒｉｓｏｘａｚｏｌｅ）、ピリダクロメチル（ｐｙｒｉｄａｃｈｌｏｍｅｔｙｌ）、ピリフェノックス（ｐｙｒｉｆｅｎｏｘ）、ピリブチカルブ（ｐｙｒｉｂｕｔｉｃａｒｂ）、ピリベンカルブ（ｐｙｒｉｂｅｎｃａｒｂ）、ピリメタニル（ｐｙｒｉｍｅｔｈａｎｉｌ）、ピロキロン（ｐｙｒｏｑｕｉｌｏｎ）、ビンクロゾリン（ｖｉｎｃｌｏｚｏｌｉｎ）、ファーバム（ｆｅｒｂａｍ）、ファモキサドン（ｆａｍｏｘａｄｏｎｅ）、フェナジンオキシド（ｐｈｅｎａｚｉｎｅ　ｏｘｉｄｅ）、フェナミドン（ｆｅｎａｍｉｄｏｎｅ）、フェナミンストロビン（ｆｅｎａｍｉｎｓｔｒｏｂｉｎ）、フェナリモル（ｆｅｎａｒｉｍｏｌ）、フェノキサニル（ｆｅｎｏｘａｎｉｌ）、フェリムゾン（ｆｅｒｉｍｚｏｎｅ）、フェンピクロニル（ｆｅｎｐｉｃｌｏｎｉｌ）、フェンピコキサミド（ｆｅｎｐｉｃｏｘａｍｉｄ）、フェンピラザミン（ｆｅｎｐｙｒａｚａｍｉｎｅ）、フェンブコナゾール（ｆｅｎｂｕｃｏｎａｚｏｌｅ）、フェンフラム（ｆｅｎｆｕｒａｍ）、フェンプロピジン（ｆｅｎｐｒｏｐｉｄｉｎ）、フェンプロピモルフ（ｆｅｎｐｒｏｐｉｍｏｒｐｈ）、フェンヘキサミド（ｆｅｎｈｅｘａｍｉｄ）、フォルペット（ｆｏｌｐｅｔ）、フサライド（ｐｈｔｈａｌｉｄｅ）、ブピリメート（ｂｕｐｉｒｉｍａｔｅ）、フベリダゾール（ｆｕｂｅｒｉｄａｚｏｌｅ）、ブラストサイジン－Ｓ（ｂｌａｓｔｉｃｉｄｉｎ－Ｓ）、フラメトピル（ｆｕｒａｍｅｔｐｙｒ）、フララキシル（ｆｕｒａｌａｘｙｌ）、フランカルボン酸（ｆｕｒａｎｃａｒｂｏｘｙｌｉｃ　ａｃｉｄ）、フルアジナム（ｆｌｕａｚｉｎａｍ）、フルインダピル（ｆｌｕｉｎｄａｐｙｒ）、フルオキサストロビン（ｆｌｕｏｘａｓｔｒｏｂｉｎ）、フルオキサピプロリン（ｆｌｕｏｘａｐｉｐｒｏｌｉｎ）、フルオピコリド（ｆｌｕｏｐｉｃｏｌｉｄｅ）、フルオピモミド（ｆｌｕｏｐｉｍｏｍｉｄｅ）、フルオピラム（ｆｌｕｏｐｙｒａｍ）、フルオルイミド（ｆｌｕｏｒｏｉｍｉｄｅ）、フルキサピロキサド（ｆｌｕｘａｐｙｒｏｘａｄ）、フルキンコナゾール（ｆｌｕｑｕｉｎｃｏｎａｚｏｌｅ）、フルコナゾール（ｆｕｒｃｏｎａｚｏｌｅ）、フルコナゾール・シス（ｆｕｒｃｏｎａｚｏｌｅ　－ｃｉｓ）、フルジオキソニル（ｆｌｕｄｉｏｘｏｎｉｌ）、フルシラゾール（ｆｌｕｓｉｌａｚｏｌｅ）、フルスルファミド（ｆｌｕｓｕｌｆａｍｉｄｅ）、フルチアニル（ｆｌｕｔｉａｎｉｌ）、フルトラニル（ｆｌｕｔｏｌａｎｉｌ）、フルトリアホール（ｆｌｕｔｒｉａｆｏｌ）、フルフェノキシストロビン（ｆｌｕｆｅｎｏｘｙｓｔｒｏｂｉｎ）、フルメトベル（ｆｌｕｍｅｔｏｖｅｒ）、フルモルフ（ｆｌｕｍｏｒｐｈ）、プロキナジド（ｐｒｏｑｕｉｎａｚｉｄ）、プロクロラズ（ｐｒｏｃｈｌｏｒａｚ）、プロシミドン（ｐｒｏｃｙｍｉｄｏｎｅ）、プロチオカルブ（ｐｒｏｔｈｉｏｃａｒｂ）、プロチオコナゾール（ｐｒｏｔｈｉｏｃｏｎａｚｏｌｅ）、ブロノポール（ｂｒｏｎｏｐｏｌ）、プロパモカルブ塩酸塩（ｐｒｏｐａｍｏｃａｒｂ－ｈｙｄｒｏｃｈｌｏｒｉｄｅ）、プロピコナゾール（ｐｒｏｐｉｃｏｎａｚｏｌｅ）、プロピネブ（ｐｒｏｐｉｎｅｂ）、プロベナゾール（ｐｒｏｂｅｎａｚｏｌｅ）、ブロムコナゾール（ｂｒｏｍｕｃｏｎａｚｏｌｅ）、フロメトキン（ｆｌｏｍｅｔｏｑｕｉｎ）、フロリルピコキサミド（ｆｌｏｒｙｌｐｉｃｏｘａｍｉｄ
）、ヘキサコナゾール（ｈｅｘａｃｏｎａｚｏｌｅ）、ベナラキシル（ｂｅｎａｌａｘｙｌ）、ベナラキシル・Ｍ（ｂｅｎａｌａｘｙｌ－Ｍ）、ベノダニル（ｂｅｎｏｄａｎｉｌ）、ベノミル（ｂｅｎｏｍｙｌ）、ペフラゾエート（ｐｅｆｕｒａｚｏａｔｅ）、ペンコナゾール（ｐｅｎｃｏｎａｚｏｌｅ）、ペンシクロン（ｐｅｎｃｙｃｕｒｏｎ）、ベンゾビンジフルピル（ｂｅｎｚｏｖｉｎｄｉｆｌｕｐｙｒ）、ベンチアゾール（ｂｅｎｔｈｉａｚｏｌｅ）、ベンチアバリカルブ・イソプロピル（ｂｅｎｔｈｉａｖａｌｉｃａｒｂ－ｉｓｏｐｒｏｐｙｌ）、ペンチオピラド（ｐｅｎｔｈｉｏｐｙｒａｄ）、ペンフルフェン（ｐｅｎｆｌｕｆｅｎ）、ボスカリド（ｂｏｓｃａｌｉｄ）、ホセチル（ｆｏｓｅｔｙｌ）（ａｌｍｉｎｉｕｍ，　ｃａｌｃｉｕｍ，　ｓｏｄｉｕｍ）、ポリオキシン（ｐｏｌｙｏｘｉｎ）、ポリカーバメート（ｐｏｌｙｃａｒｂａｍａｔｅ）、ボルドー液（Ｂｏｒｄｅａｕｘ　ｍｉｘｔｕｒｅ）、マンカッパー（ｍａｎｃｏｐｐｅｒ）、マンコゼブ（ｍａｎｃｏｚｅｂ）、マンジプロパミド（ｍａｎｄｉｐｒｏｐａｍｉｄ）、マンデストロビン（ｍａｎｄｅｓｔｒｏｂｉｎ）、マンネブ（ｍａｎｅｂ）、ミクロブタニル（ｍｙｃｌｏｂｕｔａｎｉｌ）、ミネラルオイル（ｍｉｎｅｒａｌ　ｏｉｌｓ）、ミルディオマイシン（ｍｉｌｄｉｏｍｙｃｉｎ）、メタスルホカルブ（ｍｅｔｈａｓｕｌｆｏｃａｒｂ）、メタム（ｍｅｔａｍ）、メタラキシル（ｍｅｔａｌａｘｙｌ）、メタラキシル・Ｍ（ｍｅｔａｌａｘｙｌ－Ｍ）、メチラム（ｍｅｔｉｒａｍ）、メチルテトラプロール（ｍｅｔｙｌｔｅｔｒａｐｒｏｌｅ）、メトコナゾール（ｍｅｔｃｏｎａｚｏｌｅ）、メトミノストロビン（ｍｅｔｏｍｉｎｏｓｔｒｏｂｉｎ）、メトラフェノン（ｍｅｔｒａｆｅｎｏｎｅ）、メパニピリム（ｍｅｐａｎｉｐｙｒｉｍ）、メフェントリフルコナゾール（ｍｅｆｅｎｔｒｉｆｌｕｃｏｎａｚｏｌｅ）、メプチルジノカップ（ｍｅｐｔｙｌｄｉｎｏｃａｐ）、メプロニル（ｍｅｐｒｏｎｉｌ）、ヨードカルブ（ｉｏｄｏｃａｒｂ）、ラミナリン（ｌａｍｉｎａｒｉｎ）、リゾビウム・ビティス（Ｒｈｉｚｏｂｉｕｍ　ｖｉｔｉｓ）、亜リン酸及び塩（ｐｈｏｓｐｈｏｒｏｕｓ　ａｃｉｄ　ａｎｄ　ｓａｌｔｓ）、塩基性塩化銅（ｃｏｐｐｅｒ　ｏｘｙｃｈｌｏｒｉｄｅ）、銀（ｓｉｌｖｅｒ）、酸化第一銅（ｃｕｐｒｏｕｓ　ｏｘｉｄｅ）、水酸化第二銅（ｃｏｐｐｅｒ　ｈｙｄｒｏｘｉｄｅ）、炭酸水素カリウム（ｐｏｔａｓｓｉｕｍ　ｂｉｃａｒｂｏｎａｔｅ）、炭酸水素ナトリウム（ｓｏｄｉｕｍ　ｂｉｃａｒｂｏｎａｔｅ）、硫黄（ｓｕｌｆｕｒ）、硫酸オキシキノリン（ｏｘｙｑｕｉｎｏｌｉｎｅ　ｓｕｌｆａｔｅ）、硫酸銅（ｃｏｐｐｅｒ　ｓｕｌｆａｔｅ）、（３，４－ジクロロイソチアゾール－５－イル）メチル　４－（ｔｅｒｔ－ブチル）安息香酸エステル（化学名、ＣＡＳ登録番号：１２３１２１４－２３－５）、ＢＡＦ－０４５（コード番号）、ＢＡＧ－０１０（コード番号）、ＵＫ－２Ａ（コード番号）、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］（ＤＢＥＤＣ）、ＭＩＦ－１００２（コード番号）、ＮＦ－１８０（コード番号）、酢酸トリフェニルスズ（ＴＰＴＡ）、トリフェニルチンクロライド（ＴＰＴＣ）、水酸化トリフェニルスズ（ＴＰＴＨ）、非病原性エルビニア・カロトボーラ、Ｆ９６５０（コード番号）。 Fungicidal active ingredient:
Azaconazole, acibenzolar-S-methyl, azoxystrobin, anilazine, anisulbrom, amipyriffline, aminopyrifline, aminoprifectin aldimorph), isotianil, isopyrazam, isofetamide, isoflucipram, isoprothiolane, ipconifen, epuconazole, ipconazole, ipconazole, ipconazole, ipconazole, and ipconazole. Fentriffluconazole (ipfentrifluconazole), iprodione, iprovalicarb, iprobenfos, imazalilamine, iminotazine albecilate, iminoctazine albesilate (Imibenconazole), impirfluxam, imprimatin A, imprimatin B, edifenphos, etaconazol, ethaboxam aboxam), etirimol, ethoxyquin, ethridiazole, enestroburin, enoxastrobin, epoxiconil, oxyloxyxanol, oxyloxyl, oxyloxyl, oxyloxyl, oxyl, oxyl, oxyl, oxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl, xyloxyl , Oxazinylazole, oxathiapiprolin, oxycarboxin, oxyquinoline copper, oxytetracycline, oxpoconozolate e-fumarate), oxolinic acid, copper octanoate, octilinone, offurase, orysastrobin, orthophenylphenol, o-phenyka, phoenkas phenyka, phoenka phos pheny phos, and phos pheny phos pheny phos pheny phos pheny phos pheny phos pheny phos pheny phos pheny phos phos phos phos phos phos pheny phos phenol (Captafol), carpropamide (carbpropazim), carbendazim (carbendazim), carboxin (carboxin), carbonone (carbone), quinoxyfen (quinoxyfen), quinofumelin (quinothiome), quinofumine (quinothiome), quinofumeline (quinothiome) tan), quinconazole, quintozene, guazatine, guafuraneb, coufuraneb, coumethoxystrobin, cumoxystrobin, methoxystrobin, krysoxime, kresoxime, krysoxime, kresoxime, krysoxime, mexoxime, kresoxime, mexoxime, kresoxime, krexoxime, mexoxime, krexoxime, krexoxime, krexoxime, krexoxime, mexoxime, krexoxime, krexoxime, krexoxime, mexoxime, krexoxime, kryoxymoxy, krexoxime, krexoxime, krexoxime, krexoxime) (Clozylacon), clozolinate, chlorothalonil, chloroneb, cyazofamid, dietofencarb, diclosiclodimet, diclosiclomidet Diclobenthiazox, diclomezine, dichloran, dichlorophen, dithianon, dithianon, diconizazole, diconazole, M (diniconazole) dinocap), Jipimechitoron (dipymetitrone), diphenylamine (diphenylamine), difenoconazole (difenoconazole), cyflufenamid (cyflufenamid), diflumetorim (diflumetorim), cyproconazole (cyproconazole), cyprodinil (cyprodi nil), simeconazole, dimethirimol, dimethyl disulfide, dimethomorph, simoxanil, cymoxanis, dimoxi rosimo deux romoxi de simon serox deo mosin de roxio simo simon simon simon simon simon simons 0804), ziram, silthiofam, streptomycin, spiroxamine, sedoxane, sedaxane, zoxamide, solatenol, zolatenol ), Talaromyces flavus, thiazinil, thiabendazole, thiuram, thiram, thiophanate, thiophanate, thiphanate-thylamide, thiphanate-thylamide, thiphanate-thylamide, thiphanate-thylamide, thiphanate-thylamide, thiphanate-thylamide, thiphanate-thylamide, thiphanate-thylamide, thiphanate-thylamide, and thiphanate-thylamide. tecnazene, tecloftalam, tetraconazole, debacarb, tebuconazole, tebufloquine, terbinafine, terbinafine, terbinafine, terbinafine odemorph, triadimenol, triadimefon, triazoxide, trichlamide, triclopyric carb, trichoderico trocyl, trichoderzol trichloride, trichodrosol trichloride ), Tridemorph, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl (tolclofo) s-methyl), tolnifanide, tolprocarb, nabam, natamycin, naftifine, nitrapyrin, nitrapyl rin, nitrotal propyl, nitrotal roline, nitrotal roline, nitropyrine Copper nonylphenol sulfonate (copper nonyl phenol sulphonate), Bacillus subtilis (strain: QST 713), validamycin (validamycin), valifenalate, picalxazo, picalxazo, picicalbux, picicalbux, picicalxtra (Bixafen), picoxystrobin, pydiflumetofen, bitertanol, binapacryl, hinokitiol, biphenyl (hypha), biphenyl (hypyl, hyphyl, hyphyl, hyphyl, hyphyl, hyphyl, hyphyl, hyphyl) , Pyraoxystrobin, pyraclostrobin, pyraziflumide, pyrazophos, pyrapropoine, pyramethropioni, pyrametostrobin (pyrametostrobin) e), Pirisokisazoru (pyrisoxazole), pyridinium DACRO methyl (pyridachlometyl), pyrifenox (pyrifenox), pyributicarb (pyributicarb), pyribencarb (pyribencarb), pyrimethanil (pyrimethanil), pyroquilon (pyroquilon), vinclozolin (vinclozolin), Fabamu (Ferbam ), Famoxadone, phenazine oxide, phenamidone, phenaminestrobin, fenarimol, fenoxanil, feminzoner e), fenpiclonil, fenpicoxamide, fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropidin, fenpropidin, fenpropidin (Fenhexamid), folpet, phthalide, bupirimate, fuberidazole, blasticidin-S, furamepyr, furametpyr, furametpyr, furametpyr, furametpyr, furametpyr, furametpyr, furametpyr) furan arboxylic acid, fluazinam, fluindapyr, fluoxapromide, fluoxapiromide, fluopipolomide, fluopipolomide, fluopipolomide, fluopipromide, fluopipolomide Fluxapyroxad, fluquinconazole, fluconazole, fluconazole-cis, fludioxonil, flusilazol Flusulfamide (flusulfamide), Furuchianiru (flutianil), flutolanil (flutolanil), flutriafol (flutriafol), full phenoxy cysts Robin (flufenoxystrobin), Furumetoberu (flumetover), flumorph (flumorph), proquinazid (proquinazid), prochloraz (Prochloraz), Procymidone, prothiocarb, prothioconazole, bronopol, propamocarb-hydrochloride, propiconazole, propiconazole, propioconazole, prothiocarbone, prothioconazole, prothioconazole, prothioconazole, bronopol, propamocarb-hydrochloride, propiconazole Ropinebu (propineb), probenazole (probenazole), bromuconazole (bromuconazole), Furometokin (flometoquin), fluoridation Le pico alkylcarboxamide (Florylpicoxamid
), Hexaconazole, benalaxyl, benalaxyl-M, benodanil, benomyl, benomyl, pefurazoate, benzophenone, benzophenone, benzophenone, benzophenone, benzophenone, benzophenone, benzophenone, benzophenone, benzophenone, benzophenone, benzophenone, benzophenone, benzophenone, benzophenone, benzophenone, benzophenone, benzophenone. Diflupir (benzovindiflupyr), benthiazole (benthiazole), benthiavalicarb-isopropyl, penthiopyrad, penflufen, scafylid, scafylid, scalido, scalido, scalido, scalido, scalide, boscalid, sc lcium, sodium, polyoxin, polycarbamate, bordeaux mixture, mancopper, mancozeb, mandeb, mandiopropamide Microbutanil, mineral oils, mildiomycin, methasulfocarb, metatam, metalaxyl, metalaxyl, metalaxyl, metalaxyl, metalaxyl, metalaxyl, metalaxyl Methyl tet Protol (metyltetraprole), metconazole (metconazole), methinostrobin (metaminostrobin), metrafenone (metrafenone), mepanipyrim (mepanipyrim), mefentrifluconyl melontricono meconipol meconiplon melonponicol iodocarb, laminarin, Rhizobium vitis, phosphorous acid and salts, basic copper chloride, silver oxide, silver oxide xide), cupper hydroxide, potassium bicarbonate, sodium bicarbonate, sulfur, sulfur, oxyquinoline sulfate, copper sulfate, copper sulfate 3,4-dichloroisothiazol-5-yl) methyl 4- (tert-butyl) benzoate (chemical name, CAS registry number: 1231214-23-5), BAF-045 (code number), BAG-010 ( Code number), UK-2A (code number), bisethylenediamine copper complex salt of dodecylbenzenesulfonic acid [II] (DBEDC), MIF-1002 (code number), NF-180 (code number) No.), triphenyltin acetate (TPTA), triphenyltin chloride (TPTC), triphenyltin hydroxide (TPTH), non-pathogenic Erwinia carotobola, F9650 (code number).
　次に、混合又は併用してもよい公知の除草剤化合物、植物生長調整剤化合物を以下に例示する。 Next, known herbicide compounds and plant growth regulator compounds that may be mixed or used in combination are exemplified below.
　除草活性成分：
　アイオキシニル（ｉｏｘｙｎｉｌ）、アクロニフェン（ａｃｌｏｎｉｆｅｎ）、アクロレイン（ａｃｒｏｌｅｉｎ）、アザフェニジン（ａｚａｆｅｎｉｄｉｎ）、アシフルオルフェン（ａｃｉｆｌｕｏｒｆｅｎ）（ナトリウムなどとの塩を含む）、アジムスルフロン（ａｚｉｍｓｕｌｆｕｒｏｎ）、アシュラム（ａｓｕｌａｍ）、アセトクロ－ル（ａｃｅｔｏｃｈｌｏｒ）、アトラジン（ａｔｒａｚｉｎｅ）、アニロホス（ａｎｉｌｏｆｏｓ）、アミカルバゾン（ａｍｉｃａｒｂａｚｏｎｅ）、アミドスルフロン（ａｍｉｄｏｓｕｌｆｕｒｏｎ）、アミトロール（ａｍｉｔｒｏｌｅ）、アミノシクロピラクロル（ａｍｉｎｏｃｙｃｌｏｐｙｒａｃｈｌｏｒ）、アミノピラリド（ａｍｉｎｏｐｙｒａｌｉｄ）、アミプロホス・メチル（ａｍｉｐｒｏｆｏｓ－ｍｅｔｈｙｌ）、アメトリン（ａｍｅｔｒｙｎ）、アラクロール（ａｌａｃｈｌｏｒ）、アロキシジム（ａｌｌｏｘｙｄｉｍ）、アンシミドール（ａｎｃｙｍｉｄｏｌ）、イソウロン（ｉｓｏｕｒｏｎ）、イソキサクロルトール（ｉｓｏｘａｃｈｌｏｒｔｏｌｅ）、イソキサフルトール（ｉｓｏｘａｆｌｕｔｏｌｅ）、イソキサベン（ｉｓｏｘａｂｅｎ）、イソデシルアルコールエトキシレート（Ｉｓｏｄｅｃｙｌａｌｋｏｈｏｌｅｔｈｏｘｙｌａｔｅ）、イソプロツロン（ｉｓｏｐｒｏｔｕｒｏｎ）、イプフェンカルバゾン（ｉｐｆｅｎｃａｒｂａｚｏｎｅ）、イマザキン（ｉｍａｚａｑｕｉｎ）、イマザピク（ｉｍａｚａｐｉｃ）（アミン等との塩を含む）、イマザピル（ｉｍａｚａｐｙｒ）（イソプロピルアミン等の塩を含む）、イマザメタベンズ（ｉｍａｚａｍｅｔｈａｂｅｎｚ－ｍｅｔｈｙｌ）、イマザモックス（ｉｍａｚａｍｏｘ）、イマゼタピル（ｉｍａｚｅｔｈａｐｙｒ）、イマゾスルフロン（ｉｍａｚｏｓｕｌｆｕｒｏｎ）、インダジフラム（ｉｎｄａｚｉｆｌａｍ）、インダノファン（ｉｎｄａｎｏｆａｎ）、エグリナジン・エチル（ｅｇｌｉｎａｚｉｎｅ－ｅｔｈｙｌ）、エスプロカルブ（ｅｓｐｒｏｃａｒｂ）、エタメトスルフロン・メチル（ｅｔｈａｍｅｔｓｕｌｆｕｒｏｎ－ｍｅｔｈｙｌ）、エタルフルラリン（ｅｔｈａｌｆｌｕｒａｌｉｎ）、エチジムロン（ｅｔｈｉｄｉｍｕｒｏｎ）、エトキシスルフロン（ｅｔｈｏｘｙｓｕｌｆｕｒｏｎ）、エトキシフェン（ｅｔｈｏｘｙｆｅｎ－ｅｔｈｙｌ）、エトフメセート（ｅｔｈｏｆｕｍｅｓａｔｅ）、エトベンザニド（ｅｔｏｂｅｎｚａｎｉｄ）、エンドタール二ナトリウム塩（ｅｎｄｏｔｈａｌ－ｄｉｓｏｄｉｕｍ）、オキサジアゾン（ｏｘａｄｉａｚｏｎ）、オキサジアルギル（ｏｘａｄｉａｒｇｙｌ）、オキサジクロメホン（ｏｘａｚｉｃｌｏｍｅｆｏｎｅ）、オキサスルフロン（ｏｘａｓｕｌｆｕｒｏｎ）、オキシフルオルフェン（ｏｘｙｆｌｕｏｒｆｅｎ）、オリザリン（ｏｒｙｚａｌｉｎ）、オルトスルファムロン（ｏｒｔｈｏｓｕｌｆａｍｕｒｏｎ）、オルベンカルブ（ｏｒｂｅｎｃａｒｂ）、オレイン酸（ｏｌｅｉｃ　ａｃｉｄ）、カフェンストロール（ｃａｆｅｎｓｔｒｏｌｅ）、カルフェントラゾン・エチル（ｃａｒｆｅｎｔｒａｚｏｎｅ－ｅｔｈｙｌ）、カルブチレート（ｋａｒｂｕｔｉｌａｔｅ）、カルベタミド（ｃａｒｂｅｔａｍｉｄｅ）、キザロホップ（ｑｕｉｚａｌｏｆｏｐ）、キザロホップ・エチル（ｑｕｉｚａｌｏｆｏｐ－ｅｔｈｙｌ）、キザロホップ・Ｐ・エチル（ｑｕｉｚａｌｏｆｏｐ－Ｐ－ｅｔｈｙｌ）、キザロホップ・Ｐ・テフリル（ｑｕｉｚａｌｏｆｏｐ－Ｐ－ｔｅｆｕｒｙｌ）、キノクラミン（ｑｕｉｎｏｃｌａｍｉｎｅ）、キンクロラック（ｑｕｉｎｃｌｏｒａｃ）、キンメラック（ｑｕｉｎｍｅｒａｃ）、クミルロン（ｃｕｍｙｌｕｒｏｎ）、クラシホス（ｃｌａｃｙｆｏｓ）、グリホサート（ｇｌｙｐｈｏｓａｔｅ）（ナトリウム、カリウム、アミン、プロピルアミン、イソプロピルアミン、ジメチルアミン又はトリメシウム等の塩を含む）、グルホシネート（ｇｌｕｆｏｓｉｎａｔｅ）（アミン又はナトリウム等の塩を含む）、グルホシネート・Ｐ（ｇｌｕｆｏｓｉｎａｔｅ－Ｐ）、グルホシネート・Ｐ・ナトリウム塩（ｇｌｕｆｏｓｉｎａｔｅ－Ｐ－ｓｏｄｉｕｍ）、クレトジム（ｃｌｅｔｈｏｄｉｍ）、クロジナホップ・プロパルギル（ｃｌｏｄｉｎａｆｏｐ－ｐｒｏｐａｒｇｙｌ）、クロピラリド（ｃｌｏｐｙｒａｌｉｄ）、クロマゾン（ｃｌｏｍａｚｏｎｅ）、クロメトキシフェン（ｃｈｌｏｍｅｔｈｏｘｙｆｅｎ）、クロメプロップ（ｃｌｏｍｅｐｒｏｐ）、クロランスラム・メチル（ｃｌｏｒａｎｓｕｌａｍ－ｍｅｔｈｙｌ）、クロランベン（ｃｈｌｏｒａｍｂｅｎ）、クロリダゾン（ｃｈｌｏｒｉｄａｚｏｎ）、クロリムロン・エチル（ｃｈｌｏｒｉｍｕｒｏｎ－ｅｔｈｙｌ）、クロルスルフロン（ｃｈｌｏｒｓｕｌｆｕｒｏｎ）、クロルタル・ジメチル（ｃｈｌｏｒｔｈａｌ－ｄｉｍｅｔｈｙｌ）、クロルチアミド（ｃｈｌｏｒｔｈｉａｍｉｄ）、クロルフタリム（ｃｈｌｏｒｐｈｔｈａｌｉｍ）、クロルフルレノール・メチル（ｃｈｌｏｒｆｌｕｒｅｎｏｌ－ｍｅｔｈｙｌ）、クロルプロファム（ｃｈｌｏｒｐｒｏｐｈａｍ）、クロルブロムロン（ｃｈｌｏｒｂｒｏｍｕｒｏｎ）、クロロクスロン（ｃｈｌｏｒｏｘｕｒｏｎ）、クロロトルロン（ｃｈｌｏｒｏｔｏｌｕｒｏｎ）、ケトスピラドックス（ｋｅｔｏｓｐｉｒａｄｏｘ）（ナトリウム、カルシウム又はアンモニアなどの塩を含む）、サフルフェナシル（ｓａｆｌｕｆｅｎａｃｉｌ）、サルメンチン（ｓａｒｍｅｎｔｉｎｅ）、シアナジン（ｃｙａｎａｚｉｎｅ）、シアナミド（ｃｙａｎａｍｉｄｅ）、ジウロン（ｄｉｕｒｏｎ）、ジエタチル・エチル（ｄｉｅｔｈａｔｙｌ－ｅｔｈｙｌ）、ジカンバ（ｄｉｃａｍｂａ）（アミン、ジエチルアミン、イソプロピルアミン、ジグリコールアミン、ナトリウム又はリチウム等の塩を含む）、シクロエート（ｃｙｃｌｏａｔｅ）、シクロキシジム（ｃｙｃｌｏｘｙｄｉｍ）、ジクロスラム（ｄｉｃｌｏｓｕｌａｍ）、シクロスルファムロン（ｃｙｃｌｏｓｕｌｆａｍｕｒｏｎ）、シクロピラニル（ｃｙｃｌｏｐｙｒａｎｉｌ）、シクロピリモレート（ｃｙｃｌｏｐｙｒｉｍｏｒａｔｅ）、ジクロベニル（ｄｉｃｈｌｏｂｅｎｉｌ）、ジクロホップ・Ｐ・メチル（ｄｉｃｌｏｆｏｐ－Ｐ－ｍｅｔｈｙｌ）、ジクロホップ・メチル（ｄｉｃｌｏｆｏｐ－ｍｅｔｈｙｌ）、ジクロルプロップ（ｄｉｃｈｌｏｒｐｒｏｐ）、ジクロルプロップ－Ｐ（ｄｉｃｈｌｏｒｐｒｏｐ－Ｐ）、ジクワット（ｄｉｑｕａｔ）、ジチオピル（ｄｉｔｈｉｏｐｙｒ）、シデュロン（ｓｉｄｕｒｏｎ）、ジニトラミン（ｄｉｎｉｔｒａｍｉｎｅ）、シニドン・エチル（ｃｉｎｉｄｏｎ－ｅｔｈｙｌ）、シノスルフロン（ｃｉｎｏｓｕｌｆｕｒｏｎ）、ジノゼブ（ｄｉｎｏｓｅｂ）、ジノテルブ（ｄｉｎｏｔｅｒｂ）、シハロホップ・ブチル（ｃｙｈａｌｏｆｏｐ－ｂｕｔｙｌ）、ジフェナミド（ｄｉｐｈｅｎａｍｉｄ）、ジフェンゾコート（ｄｉｆｅｎｚｏｑｕａｔ）、ジフルフェニカン（ｄｉｆｌｕｆｅｎｉｃａｎ）、ジフルフェンゾピル（ｄｉｆｌｕｆｅｎｚｏｐｙｒ）、シマジン（ｓｉｍａｚｉｎｅ）、ジメタクロール（ｄｉｍｅｔｈａｃｈｌｏｒ）、ジメタメトリン（ｄｉｍｅｔｈａｍｅｔｒｙｎ）、ジメテナミド（ｄｉｍｅｔｈｅｎａｍｉｄ）、ジメテナミド・Ｐ（ｄｉｍｅｔｈｅｎａｍｉｄ－Ｐ）、シメトリン（ｓｉｍｅｔｒｙｎ）、ジメピペレート（ｄｉｍｅｐｉｐｅｒａｔｅ）、ジメフロン（ｄｉｍｅｆｕｒｏｎ）、シンメチリン（ｃｉｎｍｅｔｈｙｌｉｎ）、スエップ（ｓｗｅｐ）、スルコトリオン（ｓｕｌｃｏｔｒｉｏｎｅ）、スルフェントラゾン（ｓｕｌｆｅｎｔｒａｚｏｎｅ）、スルホサート（ｓｕｌｆｏｓａｔｅ）、スルホスルフロン（ｓｕｌｆｏｓｕｌｆｕｒｏｎ）、スルホメツロンメチル（ｓｕｌｆｏｍｅｔｕｒｏｎ－ｍｅｔｈｙｌ）、セトキシジム（ｓｅｔｈｏｘｙｄｉｍ）、ターバシル（ｔｅｒｂａｃｉｌ）、ダイムロン（ｄａｉｍｕｒｏｎ）、タキストミン・Ａ（ｔｈａｘｔｏｍｉｎ　Ａ）、ダラポン（ｄａｌａｐｏｎ）、チアゾピル（ｔｈｉａｚｏｐｙｒ）、チアフェナシル（ｔｉａｆｅｎａｃｉｌ）、チエンカルバゾン（ｔｈｉｅｎｃａｒｂａｚｏｎｅ）（ナトリウム塩、メチルエステル等を含む）、チオカルバジル（ｔｉｏｃａｒｂａｚｉｌ）、チオベンカルブ（ｔｈｉｏｂｅｎｃａｒｂ）、チジアジミン（ｔｈｉｄｉａｚｉｍｉｎ）、チジアズロン（ｔｈｉｄｉａｚｕｒｏｎ）、チフェンスルフロン・メチル（ｔｈｉｆｅｎｓｕｌｆｕｒｏｎ－ｍｅｔｈｙｌ）、デスメディファム（ｄｅｓｍｅｄｉｐｈａｍ）、デスメトリン（ｄｅｓｍｅｔｒｙｎｅ）、テトフルピリメット（ｔｅｔｆｌｕｐｙｒｏｌｉｍｅｔ）、テニルクロール（ｔｈｅｎｙｌｃｈｌｏｒ）、テブタム（ｔｅｂｕｔａｍ）、テブチウロン（ｔｅｂｕｔｈｉｕｒｏｎ）、テプラロキシジム（ｔｅｐｒａｌｏｘｙｄｉｍ）、テフリルトリオン（ｔｅｆｕｒｙｌｔｒｉｏｎｅ）、テルブチラジン（ｔｅｒｂｕｔｈｙｌａｚｉｎｅ）、テルブトリン（ｔｅｒｂｕｔｒｙｎ）、テルブメトン（ｔｅｒｂｕｍｅｔｏｎ）、テンボトリオン（ｔｅｍｂｏｔｒｉｏｎｅ）、トプラメゾン（ｔｏｐｒａｍｅｚｏｎｅ）、トラルコキシジム（ｔｒａｌｋｏｘｙｄｉｍ）、トリアジフラム（ｔｒｉａｚｉｆｌａｍ）、トリアスルフロン（ｔｒｉａｓｕｌｆｕｒｏｎ）、トリアファモン（ｔｒｉａｆａｍｏｎｅ）、トリアレート（ｔｒｉ－ａｌｌａｔｅ）、トリエタジン（ｔｒｉｅｔａｚｉｎｅ）、トリクロピル（ｔｒｉｃｌｏｐｙｒ）、トリクロピル－ブトティル（ｔｒｉｃｌｏｐｙｒ－ｂｕｔｏｔｙｌ）、トリトスルフロン（ｔｒｉｔｏｓｕｌｆｕｒｏｎ）、トリフルジモキサジン（ｔｒｉｆｌｕｄｉｍｏｘａｚｉｎ）、トリフルスルフロン・メチル（ｔｒｉｆｌｕｓｕｌｆｕｒｏｎ－ｍｅｔｈｙｌ）、トリフルラリン（ｔｒｉｆｌｕｒａｌｉｎ）、トリフロキシスルフロンナトリウム塩（ｔｒｉｆｌｏｘｙｓｕｌｆｕｒｏｎ－ｓｏｄｉｕｍ）、トリベニュロン・メチル（ｔｒｉｂｅｎｕｒｏｎ－ｍｅｔｈｙｌ）、トルピラレート（ｔｏｌｐｙｒａｌａｔｅ）、ナプタラム（ｎａｐｔａｌａｍ）（ナトリウム等との塩を含む）、ナプロアニリド（ｎａｐｒｏａｎｉｌｉｄｅ）、ナプロパミド（ｎａｐｒｏｐａｍｉｄｅ）、ナプロパミド－Ｍ（ｎａｐｒｏｐａｍｉｄｅ－Ｍ）、ニコスルフロン（ｎｉｃｏｓｕｌｆｕｒｏｎ）、ネブロン（ｎｅｂｕｒｏｎ）、ノルフルラゾン（ｎｏｒｆｌｕｒａｚｏｎ）、バーナレート（ｖｅｒｎｏｌａｔｅ）、パラコート（ｐａｒａｑｕａｔ　ｄｉｃｈｌｏｒｉｄｅ）、ハルキシフェン・ベンジル（ｈａｌａｕｘｉｆｅｎ－ｂｅｎｚｙｌ）、ハルキシフェン・メチル（ｈａｌａｕｘｉｆｅｎ－ｍｅｔｈｙｌ）、ハロキシホップ（ｈａｌｏｘｙｆｏｐ）、ハロキシホップ・Ｐ（ｈａｌｏｘｙｆｏｐ－Ｐ）、ハロキシホップ－エトティル（ｈａｌｏｘｙｆｏｐ－ｅｔｏｔｙｌ）、ハロサフェン（ｈａｌｏｓａｆｅｎ）、ハロスルフロン・メチル（ｈａｌｏｓｕｌｆｕｒｏｎ－ｍｅｔｈｙｌ）、ビクスロゾン（ｂｉｘｌｏｚｏｎｅ）、ピクロラム（ｐｉｃｌｏｒａｍ）、ピコリナフェン（ｐｉｃｏｌｉｎａｆｅｎ）、ビシクロピロン（ｂｉｃｙｃｌｏｐｙｒｏｎｅ）、ビスピリバック・ナトリウム塩（ｂｉｓｐｙｒｉｂａｃ－ｓｏｄｉｕｍ）、ピノキサデン（ｐｉｎｏｘａｄｅｎ）、ビフェノックス（ｂｉｆｅｎｏｘ）、ピペロホス（ｐｉｐｅｒｏｐｈｏｓ）、ピラクロニル（ｐｙｒａｃｌｏｎｉｌ）、ピラスルホトール（ｐｙｒａｓｕｌｆｏｔｏｌｅ）、ピラゾキシフェン（ｐｙｒａｚｏｘｙｆｅｎ）、ピラゾスルフロン・エチル（ｐｙｒａｚｏｓｕｌｆｕｒｏｎ－ｅｔｈｙｌ）、ピラゾリネート（ｐｙｒａｚｏｌｙｎａｔｅ）、ビラナホス（ｂｉｌａｎａｆｏｓ）、ピラフルフェン・エチル（ｐｙｒａｆｌｕｆｅｎ－ｅｔｈｙｌ）、ピリダフォル（ｐｙｒｉｄａｆｏｌ）、ピリチオバック・ナトリウム塩（ｐｙｒｉｔｈｉｏｂａｃ－ｓｏｄｉｕｍ）、ピリデート（ｐｙｒｉｄａｔｅ）、ピリフタリド（ｐｙｒｉｆｔａｌｉｄ）、ピリブチカルブ（ｐｙｒｉｂｕｔｉｃａｒｂ）、ピリベンゾキシム（ｐｙｒｉｂｅｎｚｏｘｉｍ）、ピリミスルファン（ｐｙｒｉｍｉｓｕｌｆａｎ）、ピリミノバック・メチル（ｐｙｒｉｍｉｎｏｂａｃ－ｍｅｔｈｙｌ）、ピロキサスルホン
（ｐｙｒｏｘａｓｕｌｆｏｎｅ）、ピロクススラム（ｐｙｒｏｘｓｕｌａｍ）、フェニソファム（ｐｈｅｎｉｓｏｐｈａｍ）、フェニュロン（ｆｅｎｕｒｏｎ）、フェノキサスルホン（ｆｅｎｏｘａｓｕｌｆｏｎｅ）、フェノキサプロップ（ｆｅｎｏｘａｐｒｏｐ）（メチル、エチル、イソプロピルエステルを含む）、フェノキサプロップ・Ｐ（ｆｅｎｏｘａｐｒｏｐ－Ｐ）（メチル、エチル、イソプロピルエステルを含む）、フェンキノトリオン（ｆｅｎｑｕｉｎｏｔｒｉｏｎｅ）、フェンチアプロップ・エチル（ｆｅｎｔｈｉａｐｒｏｐ－ｅｔｈｙｌ）、フェントラザミド（ｆｅｎｔｒａｚａｍｉｄｅ）、フェンメディファム（ｐｈｅｎｍｅｄｉｐｈａｍ）、ブタクロール（ｂｕｔａｃｈｌｏｒ）、ブタフェナシル（ｂｕｔａｆｅｎａｃｉｌ）、ブタミホス（ｂｕｔａｍｉｆｏｓ）、ブチレート（ｂｕｔｙｌａｔｅ）、ブテナクロール（ｂｕｔｅｎａｃｈｌｏｒ）、ブトラリン（ｂｕｔｒａｌｉｎ）、ブトロキシジム（ｂｕｔｒｏｘｙｄｉｍ）、フラザスルフロン（ｆｌａｚａｓｕｌｆｕｒｏｎ）、フラムプロップ（ｆｌａｍｐｒｏｐ）（メチル、エチル、イソプロピルエステルを含む）、フラムプロップ・Ｍ（ｆｌａｍｐｒｏｐ－Ｍ）（メチル、エチル、イソプロピルエステルを含む）、プリミスルフロン・メチル（ｐｒｉｍｉｓｕｌｆｕｒｏｎ－ｍｅｔｈｙｌ）、フルアジホップ・ブチル（ｆｌｕａｚｉｆｏｐ－ｂｕｔｙｌ）、フルアジホップ・Ｐ・ブチル（ｆｌｕａｚｉｆｏｐ－Ｐ－ｂｕｔｙｌ）、フルアゾレート（ｆｌｕａｚｏｌａｔｅ）、フルオメツロン（ｆｌｕｏｍｅｔｕｒｏｎ）、フルオログリコフェン・エチル（ｆｌｕｏｒｏｇｌｙｃｏｆｅｎ－ｅｔｈｙｌ）、フルカルバゾン・ナトリウム塩（ｆｌｕｃａｒｂａｚｏｎｅ－ｓｏｄｉｕｍ）、フルクロラリン（ｆｌｕｃｈｌｏｒａｌｉｎ）、フルセトスルフロン（ｆｌｕｃｅｔｏｓｕｌｆｕｒｏｎ）、フルチアセット・メチル（ｆｌｕｔｈｉａｃｅｔ－ｍｅｔｈｙｌ）、フルピルスルフロン・メチル（ｆｌｕｐｙｒｓｕｌｆｕｒｏｎ－ｍｅｔｈｙｌ）（ナトリウム、カルシウム又はアンモニアなどの塩を含む）、フルフェナセット（ｆｌｕｆｅｎａｃｅｔ）、フルフェンピル・エチル（ｆｌｕｆｅｎｐｙｒ－ｅｔｈｙｌ）、フルプロパネート（ｆｌｕｐｒｏｐａｎａｔｅ）、フルポキサム（ｆｌｕｐｏｘａｍｅ）、フルミオキサジン（ｆｌｕｍｉｏｘａｚｉｎ）、フルミクロラック・ペンチル（ｆｌｕｍｉｃｌｏｒａｃ－ｐｅｎｔｙｌ）、フルメツラム（ｆｌｕｍｅｔｓｕｌａｍ）、フルリドン（ｆｌｕｒｉｄｏｎｅ）、フルルタモン（ｆｌｕｒｔａｍｏｎｅ）、フルロキシピル（ｆｌｕｒｏｘｙｐｙｒ）（ブトメチル、メプチル等のエステル体、ナトリウム、カルシウム又はアンモニアなどの塩を含む）、フルロクロリドン（ｆｌｕｒｏｃｈｌｏｒｉｄｏｎｅ）、プレチラクロール（ｐｒｅｔｉｌａｃｈｌｏｒ）、プロカルバゾン・ナトリウム塩（ｐｒｏｃａｒｂａｚｏｎｅ－ｓｏｄｉｕｍ）、プロジアミン（ｐｒｏｄｉａｍｉｎｅ）、プロスルフロン（ｐｒｏｓｕｌｆｕｒｏｎ）、プロスルホカルブ（ｐｒｏｓｕｌｆｏｃａｒｂ）、プロパキザホップ（ｐｒｏｐａｑｕｉｚａｆｏｐ）、プロパクロール（ｐｒｏｐａｃｈｌｏｒ）、プロパジン（ｐｒｏｐａｚｉｎｅ）、プロパニル（ｐｒｏｐａｎｉｌ）、プロピザミド（ｐｒｏｐｙｚａｍｉｄｅ）、プロピソクロール（ｐｒｏｐｉｓｏｃｈｌｏｒ）、プロピリスルフロン（ｐｒｏｐｙｒｉｓｕｌｆｕｒｏｎ）、プロファム（ｐｒｏｐｈａｍ）、プロフルアゾール（ｐｒｏｆｌｕａｚｏｌ）、プロヘキサジオン・カルシウム塩（ｐｒｏｈｅｘａｄｉｏｎｅ－ｃａｌｃｉｕｍ）、プロポキシカルバゾン（ｐｒｏｐｏｘｙｃａｒｂａｚｏｎｅ）、プロポキシカルバゾン・ナトリウム塩（ｐｒｏｐｏｘｙｃａｒｂａｚｏｎｅ－ｓｏｄｉｕｍ）、プロホキシジム（ｐｒｏｆｏｘｙｄｉｍ）、ブロマシル（ｂｒｏｍａｃｉｌ）、ブロムピラゾン（ｂｒｏｍｐｙｒａｚｏｎ）、プロメトリン（ｐｒｏｍｅｔｒｙｎ）、プロメトン（ｐｒｏｍｅｔｏｎ）、ブロモキシニル（ｂｒｏｍｏｘｙｎｉｌ）（酪酸、オクタン酸又はヘプタン酸等のエステル体を含む）、ブロモフェノキシム（ｂｒｏｍｏｆｅｎｏｘｉｍ）、ブロモブチド（ｂｒｏｍｏｂｕｔｉｄｅ）、フロラスラム（ｆｌｏｒａｓｕｌａｍ）、フロルピラキシフェン（ｆｌｏｒｐｙｒａｕｘｉｆｅｎ）、フロルピラウキシフェン・ベンジル（ｆｌｏｒｐｙｒａｕｘｉｆｅｎ－ｂｅｎｚｙｌ）、ヘキサジノン（ｈｅｘａｚｉｎｏｎｅ）、ペトキサミド（ｐｅｔｈｏｘａｍｉｄ）、ベナゾリン（ｂｅｎａｚｏｌｉｎ）、ペノキススラム（ｐｅｎｏｘｓｕｌａｍ）、ヘプタマロキシログルカン（ｈｅｐｔａｍａｌｏｘｙｌｏｇｌｕｃａｎ）、ベフルブタミド（ｂｅｆｌｕｂｕｔａｍｉｄ）、ベフルブタミド-Ｍ（ｂｅｆｌｕｂｕｔａｍｉｄ-Ｍ）、ペブレート（ｐｅｂｕｌａｔｅ）、ペラルゴン酸（ｐｅｌａｒｇｏｎｉｃ　ａｃｉｄ）、ベンカルバゾン（ｂｅｎｃａｒｂａｚｏｎｅ）、ペンジメタリン（ｐｅｎｄｉｍｅｔｈａｌｉｎ）、ベンズフェンジゾン（ｂｅｎｚｆｅｎｄｉｚｏｎｅ）、ベンスリド（ｂｅｎｓｕｌｉｄｅ）、ベンスルフロン・メチル（ｂｅｎｓｕｌｆｕｒｏｎ－ｍｅｔｈｙｌ）、ベンゾビシクロン（ｂｅｎｚｏｂｉｃｙｃｌｏｎ）、ベンゾフェナップ（ｂｅｎｚｏｆｅｎａｐ）、ベンタゾン（ｂｅｎｔａｚｏｎｅ）、ペンタノクロール（ｐｅｎｔａｎｏｃｈｌｏｒ）、ペントキサゾン（ｐｅｎｔｏｘａｚｏｎｅ）、ベンフルラリン（ｂｅｎｆｌｕｒａｌｉｎ）、ベンフレセート（ｂｅｎｆｕｒｅｓａｔｅ）、ホサミン（ｆｏｓａｍｉｎｅ）、ホメサフェン（ｆｏｍｅｓａｆｅｎ）、ホラムスルフロン（ｆｏｒａｍｓｕｌｆｕｒｏｎ）、ホルクロルフェニュロン（ｆｏｒｃｈｌｏｒｆｅｎｕｒｏｎ）、メコプロップ（ｍｅｃｏｐｒｏｐ）（ナトリウム、カリウム、イソプロピルアミン、トリエタノールアミン、ジメチルアミン等の塩を含む）、メコプロップ・Ｐ・カリウム塩（ｍｅｃｏｐｒｏｐ－Ｐ－ｐｏｔａｓｓｉｕｍ）、メソスルフロン（ｍｅｓｏｓｕｌｆｕｒｏｎ）（メチル等のエステル体含む）、メソトリオン（ｍｅｓｏｔｒｉｏｎｅ）、メタザクロール（ｍｅｔａｚａｃｈｌｏｒ）、メタゾスルフロン（ｍｅｔａｚｏｓｕｌｆｕｒｏｎ）、メタベンズチアズロン（ｍｅｔｈａｂｅｎｚｔｈｉａｚｕｒｏｎ）、メタミトロン（ｍｅｔａｍｉｔｒｏｎ）、メタミホップ（ｍｅｔａｍｉｆｏｐ）、メタム（ｍｅｔａｍ）、メタンアルソン酸二ナトリウム（ＤＳＭＡ）、メチオゾリン（ｍｅｔｈｉｏｚｏｌｉｎ）、メチルダイムロン（ｍｅｔｈｙｌｄｙｍｕｒｏｎ）、メトキスロン（ｍｅｔｏｘｕｒｏｎ）、メトスラム（ｍｅｔｏｓｕｌａｍ）、メトスルフロン・メチル（ｍｅｔｓｕｌｆｕｒｏｎ－ｍｅｔｈｙｌ）、メトブロムロン（ｍｅｔｏｂｒｏｍｕｒｏｎ）、メトベンズロン（ｍｅｔｏｂｅｎｚｕｒｏｎ）、メトラクロール（ｍｅｔｏｌａｃｈｌｏｒ）、メトリブジン（ｍｅｔｒｉｂｕｚｉｎ）、メピコート・クロリド（ｍｅｐｉｑｕａｔ　ｃｈｌｏｒｉｄｅ）、メフェナセット（ｍｅｆｅｎａｃｅｔ）、モノスルフロン（ｍｏｎｏｓｕｌｆｕｒｏｎ）（メチル、エチル、イソプロピルエステル含む）、モノリニュロン（ｍｏｎｏｌｉｎｕｒｏｎ）、モリネート（ｍｏｌｉｎａｔｅ）、ヨードスルフロン（ｉｏｄｏｓｕｌｆｕｒｏｎ）、ヨードスルフロンメチルナトリウム塩（ｉｏｄｏｓｕｌｆｕｌｏｎ－ｍｅｔｈｙｌ－ｓｏｄｉｕｍ）、ヨーフェンスルフロン（ｉｏｆｅｎｓｕｌｆｕｒｏｎ）、ヨーフェンスルフロン・ナトリウム塩（ｉｏｆｅｎｓｕｌｆｕｒｏｎ－ｓｏｄｉｕｍ）、ラクトフェン（ｌａｃｔｏｆｅｎ）、ランコトリオン（ｌａｎｃｏｔｒｉｏｎｅ）、リニュロン（ｌｉｎｕｒｏｎ）、リムスルフロン（ｒｉｍｓｕｌｆｕｒｏｎ）、レナシル（ｌｅｎａｃｉｌ）、２，２，２－トリクロロ酢酸（ＴＣＡ）（ナトリウム、カルシウム又はアンモニアなどの塩を含む）、２，３，６－トリクロロ安息香酸（２，３，６－ＴＢＡ）、２，４，５－トリクロロフェノキシ酢酸（２，４，５－Ｔ）、２，４－ジクロロフェノキシ酢酸（２，４－Ｄ）（アミン、ジエチルアミン、トリエタノールアミン、イソプロピルアミン、ナトリウム又はリチウムなどの塩を含む）、２－アミノ－３－クロロ－１，４－ナフトキノン（ＡＣＮ）、２－メチル－４－クロロフェノキシ酢酸（ＭＣＰＡ）（ナトリウム塩、エチルエステルなどを含む）、２－メチル－４－クロロフェノキシ酪酸（ＭＣＰＢ）（ナトリウム塩、エチルエステルなどを含む）、４－（２，４－ジクロロフェノキシ）酪酸（２，４－ＤＢ）、４，６－ジニトロ－Ｏ－クレゾール（ＤＮＯＣ）（アミン又はナトリウムなどの塩を含む）、ＡＥ－Ｆ‐１５０９４４（コード番号）、ＩＲ－６３９６（コード番号）、ＭＣＰＡ・チオエチル（ＭＣＰＡ－ｔｈｉｏｅｔｈｙｌ）、ＳＹＰ－２９８（コード番号）、ＳＹＰ－３００（コード番号）、Ｓ－エチルジプロピルチオカーバメート（ＥＰＴＣ）、Ｓ－メトラクロール（Ｓ－ｍｅｔｏｌａｃｈｌｏｒ）、Ｓ－９７５０（コード番号）、ＭＳＭＡ（ＭＳＭＡ）、ＨＷ－０２（コード番号）、ＮＣ－６５３（コード番号）、Ｓ―５２３（コード番号）、ＳＬ－１２０１（コード番号）。 Herbicidal active ingredients:
Ioxynil, acronifen, acrolein, azafenidin, azafenidin, acifluorfen (including salts with sodium and the like), azimsulfuron, azhamulace, ashramus (Acetochlor), atrazine (atrazine), anilofos (anilofos), amicarbazone, amidosulfuron, amitrolle, aminocyclopyrrol (amiclocyclopride), aminocyclopyracryloamidopyramylo, aminopyrrochloride, aminopyracryloamidopyramyl, aminopyrochloride, aminopyrochloride, aminopyracrylo, aminopyracrylo, aminopyracrylo, aminopyracrylamide ofos-methyl, ametrin, alachlor, alloxydim, ancymidol, isouron, isoxachlortole, isoxaflutoxol (Isoxaben), isodecyl alcohol ethoxylate (isodecyl alcohol ethoxylate), isoproturon (isoproturon), ipfencarbazone (ipfencarbazone), imazaquin (imazaquin) (including imazapic (imazapic and (icazamap)), etc. Salts such as isopropylamine No), imazamethabenz (imazamethabenz-methyl), imazamox (imazamox), imazethapyr (imazethapyr), imazosulfuron (imazosulfuron), Indajifuramu (indaziflam), indanofan (indanofan), Egurinajin-ethyl (eglinazine-ethyl), esprocarb (esprocarb), Etame Tosulfuron-methyl, ethalfluralin, ethidimuron, ethoxysulfuron, ethoxyfen-ethyl, ethofumet sate), etobenzanide, endothal-disodium salt, oxadiazon, oxadiargyl, oxadiclomefone, oxazilfolon, oxasulfuron, oxasulfuron, oxasulfuron, oxasulfuron, oxasulfuron, oxasulfuron, oxasulfuron, oxasulfuron, oxasulfuron, oxasulfuron, and oxasulfuron. ), Orthosulfamuron, orbencarb, oleic acid, cafenstrole, carfentrazone-ethyl, carbbutylate Betaamide, quizalofop, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuril, quizal-quino Quinclorac, quinmerac, cumyluron, clacyfos, glyphosate (including salts such as sodium, potassium, amine, propylamine, isopropylamine, dimethylamine or trimesium), Glufosinate (amine or sodium , Glufosinate-P, glufosinate-P-sodium salt, glutosinate-P-sodium, clethodim, clodinahop-propargyl (clodinafop-propargyl, clotinafop-propargyl) chromazone, clomethoxyphen, clomeprop, chloranslam-methyl, chloramben, chloridazon, chloriduron, chlorimyluron, chlorimyluron-chlorimylurone-chlorimyluron-chloromyluron-chlorimyluron-chloromyluron-chlorimyluron-chlorimyluron-chlorimyluron K Chlorthal-dimethyl, chlorthiamid, chlorphthalim, chlorflurenol-methyl, chlorproprom, chlorbromron, chlorbromron, chlorbromron (Chlorotoluron), ketospiradox (including salts such as sodium, calcium or ammonia), saflufenacil, salmentine, cyanamine, cyanamide, cyanamide diuron), diethtyl-ethyl, dicamba (including salts such as amine, diethylamine, isopropylamine, diglycolamine, sodium or lithium), cycloate, cycloxydim, dicloslam diclosulam), cyclosulfamuron, cyclopyranil, cyclopyrimolate, dichrobenil, diclohop-methyl, diclohop-methyl-di-clo-methyl-, di-clo-methyl-, di-cyclo-dimethyl , Dichlorprop , Dichlorprop-P, diquat, dithiopyr, siduron, dinitramine, cinidon-ethyl, sinosulfonin, cinosulfonin, sinosulfonin, sinosulfonin, cinosulfonin, cinosulfonin, cinosulfonin, cinosulfonin, cinosulfonin, cinosulfone , Dinoterb, cyhalofop-butyl, diphenamide, difenzoquat, diflufenican, diflufenzopir, diflufenzopir d methametrin, dimethenamide, dimethenamide-P, dimethenamide, simethrin, dimepiperate, dimethuron, dimethuron, dimethuron, dimethurone Tolazones (sulfentrazone), sulfosate (sulfosate), sulfosulfuron (sulfosulfuron), sulfometuron-methyl (sulfometuron-methyl), sethoxydim (sethoxydim), terbacil (terbamil), dimuron (dimablon) nA), dalapon, thiazopyr, thiafenacil, thienecarbazone (including sodium salt, methyl ester, etc.), thiocarbazil, thiobenzib, thibenzib, thibenzib, thibenzib, thibenzib, thibenzib (Thidiazuron), thifensulfuron-methyl, desmedifam, desmethrin, teflupylolimet, tenylchulbuteru, tenylchlortam (tenychlorbulte, thenylchulturbul) thiuron, tepraloxydim, tefuryltrione, terbutyrazine, terbutrynine, terbumeton, tembotrion meson, tembotrion meson ), Triasulfuron, triafamone, tri-allate, trietazine, triclopyr, triclopyr-butytyl, triclopyr-butytyl Sulfuron (tritosulfuron), trifludimoxazine, triflusulfuron-methyl, triflururalin, trifloxysulfuron, trifloxysulfuron-methyl, trifloxysulfuron-methyl sulfate Tolpyralate, naptalam (including salts with sodium and the like), naproanilide, napropamide, napropamide, napropamide-M, nicosulfuron, urnicone , Norflurazon (norflurazon), a burner rate (vernolate), paraquat (paraquat dichloride), Harukishifen benzyl (halauxifen-benzyl), Harukishifen-methyl (halauxifen-methyl), haloxyfop (haloxyfop), haloxyfop · P (haloxyfop-P), Haloxyfop-ethotyl, halosafen, halosulfuron-methyl, haloxulfuron-methyl, bixlozone, picloram, picolinacyclone, picolinacyclone, picolinacyclone Spiribac sodium salt (bispyribac-sodium), pinoxaden (pinoxaden), bifenox (pifenox), piperophos (pyperophonil), pyraclonil (pyraclonil), pyrasulfothyl (pyrazulofroxyroxypyrazofyl) ), Pyrazolynate, bilanafos, pyraflufen-ethyl, pyridafol, pyridiobac-sodium, pyritiobac-sodidium, pyridate, pyridate, pyridate, pyridate Rifalid), pyributicarb, pyribenzoxim, pyrimisulfan, pyriminobac-methyl, piroxasulfon, piroxasulfonum, pyroxenus, pyroxenus, pyroxenusulfonum Phenoxasulfone, fenoxaprop (including methyl, ethyl, and isopropyl esters), fenoxaprop-P (including fenoxaprop-P) (including methyl, ethyl, and isopropyl esters), phenquinotrione ( fenquinotrion ), Fenthiaprop-ethyl, fentrazamide, phenmedipham, butachlor, butafenacil, butamorphate, butamybutabutabutabutabutabutabutabutabutabutabutabutabutabutabutabutabutabutabutabutabutabutabutabutabutabutabutyrate Butralin, butroxydim, flazasulfuron, flamprop (including methyl, ethyl and isopropyl esters), flamprop-M (methyl, ethyl and isopropyl esters) Includes), primisulfuron methyl (Primisulfuron-methyl), fluazifop-butyl, fluazifop-P-butyl, fluazolate, fluometuron-ethylo-glyflon-glycofenol-glycolone-fluorometholone-glycofulone-fluorometholone-glycofulone-fluoromethylon-glycofulone-fluorene-glycolone-fluoromethyurone-glycolone-fluorometholone -Sodium salt (flucarbazone-sodium), fluchloralin (fluchloralin), flucetosulfuron (flucetosulfuron), fluthiacet-methyl (fluthiacet-methyl), flupyrsulfuron-methyl (flupyrurthulfurmonium or calcium calcium Flufenacet), flufenpyr-ethyl, flupropanate, flupoxame, flumioxazin, flumicroc-amcyl pentyl pentyl), flumetsulam, fluridone, flurtamone, flurtamone, fluroxypyr (esters such as butmethyl, meptyl, etc., salts such as sodium, calcium or ammonia), flurochloridone, flurochloridone Pretilachlor, procarbazo -Sodium salt (procarbazone-sodium), prodiamine (prodiamine), prosulfuron (prosulfuron), prosulfocarb (prosulfocarb), propaquizafop, propachlorprol (propachlorprol, propapropanol) , Propyzamide, propisochlor, propylisulfuron, propham, profluazol, profluazol, prohexadione-carboxycarboxy salt rbzone), propoxycarbazone-sodium, propoxydim, bromacil, bromacil, brompyrazon, octamyl acid, promethrin, xymetonyn, prometryn, xymetonyn, rometyron, xymetonyn, rometyron, xymetonyn, rometyron, xymetonyn, rometonyn, rometyron, xymetonyn, rometony, rometony, rometyron, rometyron, prometryn, roxamyl, prometryn, rometonyn, prometryn, prometryn, rometonine, ropromion, prometryn, rometonium, rometony, prometryn, prometryn, rometony, prometryn, prometryn, rometyron, prometryn, prometryn, bromomethyron, rometonyn, ropromion, prometryn, rometon, prometryn, prometryn. Including esters such as heptanoic acid), bromophenoxime, bromobutide, florasulam, florpyrauxifen, florpyrauxifenhexyl, and florpyraxenixen-hexyl. none), petoxamide (petoxamid), benazoline (benazolin), penoxsulam (penoxsulam), heptamaloxyloglucan (heptamaloxyloglucan), beflubutamate (beflubutamid), beflubutamate ), Bencarbazone, pendimethalin, benzfendizone, bensulide, bensulfuron-methyl, benzobicyclone, benzobicyclophenic acid Benzofenap, bentazone, pentanochlor, pentoxazone, pentoxazone, benfluralin, benfurasate, benfuresate, fosaforen, fomesafron, fomesaffen, fomesafen, formesafen Neuron (forchlorfenuron), mecoprop (including salts such as sodium, potassium, isopropylamine, triethanolamine, dimethylamine), mecoprop-P-potassium salt, mecosulfuron (mesosulfuron) Este such as methyl Body), mesotrione, metazachlor, metazosulfuron, methabenzthiazuron, metamitron (metamitron), metamimifon (metamimisotam) DSMA), methiozolin, methyldimethyluron, methoxuron, methosuram, metsulfuron-methyl, methobromuron metrotronurone, metobromuron melon, metrobromuron metrotronurone metolaclor, metribuzin, mepiquat chloride, mefenacet, monosulfuron (including methyl, ethyl, isopropyl ester), monolinuron, folio, morino sulphon, morinolone ), Iodosulfuron-methyl sodium salt (iodosulfuron-methyl-sodium), iofensulfuron, iofensulfuron-sodium, iofensulfuron-sodium, lactofen, lancotrione , Linuron, rimsulfuron, lenacil, 2,2,2-trichloroacetic acid (TCA) (including salts such as sodium, calcium or ammonia), 2,3,6-trichlorobenzoic acid (2,3,6-TBA), 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), 2,4-dichlorophenoxyacetic acid (2,4-D) (amine, diethylamine, triethanol Amine, isopropylamine, including salts such as sodium or lithium), 2-amino-3-chloro-1,4-naphthoquinone (ACN), 2-methyl-4-chlorophenoxyacetic acid (MCPA) (sodium salt, ethyl ester Etc.), 2-methyl-4-chlorophenoxybutyric acid (MCPB) (sodium salt) Ethyl ester, etc.), 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB), 4,6-dinitro-O-cresol (DNOC) (including salts such as amine or sodium), AE -F-150944 (code number), IR-6396 (code number), MCPA-thioethyl (MCPA-thioethyl), SYP-298 (code number), SYP-300 (code number), S-ethyldipropylthiocarbamate ( EPTC), S-metolachlor, S-9750 (code number), MSMA (MSMA), HW-02 (code number), NC-653 (code number), S-523 (code number), SL-1201 (code number).
　植物生長調節剤：
　１－ナフチルアセトアミド（１－ｎａｐｈｔｈｙｌａｃｅｔａｍｉｄｅ）、１－メチルシクロプロペン（１－ｍｅｔｈｙｌｃｙｃｌｏｐｒｏｐｅｎｅ）、２，６－ジイソプロピルナフタレン（２，６－ｄｉｉｓｏｐｒｏｐｙｌｎａｐｈｔｈａｌｅｎｅ）、４－オキソ－４－（２－フェニルエチル）アミノ酪酸（化学名、ＣＡＳ登録番号：１０８３－５５－２）、４－クロロフェノキシ酢酸（４－ＣＰＡ）、ｎ－デシルアルコール（ｎ－ｄｅｃａｎｏｌ）、アビグリシン（ａｖｉｇｌｙｃｉｎｅ）、アンシミドール（ａｎｃｙｍｉｄｏｌ）、アブシジン酸（ａｂｓｃｉｓｉｃ　ａｃｉｄ）、イナベンフィド（ｉｎａｂｅｎｆｉｄｅ）、インドール酢酸（ｉｎｄｏｌｅ　ａｃｅｔｉｃ　ａｃｉｄ）、インドール酪酸（ｉｎｄｏｌｅ　ｂｕｔｙｒｉｃ　ａｃｉｄ）、ウニコナゾール（ｕｎｉｃｏｎａｚｏｌｅ）、ウニコナゾール－Ｐ（ｕｎｉｃｏｎａｚｏｌｅ－Ｐ）、エコリスト（Ｅｃｏｌｙｓｔ）、エチクロゼート（ｅｔｈｙｃｈｌｏｚａｔｅ）、エテホン（ｅｔｈｅｐｈｏｎ）、エポコレオン（ｅｐｏｃｈｏｌｅｏｎｅ）、オキシン硫酸塩（ｏｘｉｎｅ－ｓｕｌｆａｔｅ）、カルボネ（ｃａｒｖｏｎｅ）、ギ酸カルシウム（ｃａｌｃｉｕｍ　ｆｏｒｍａｔｅ）、クロキシホナック（ｃｌｏｘｙｆｏｎａｃ）、クロキシホナック・カリウム塩（ｃｌｏｘｙｆｏｎａｃ－ｐｏｔａｓｓｉｕｍ）、クロプロップ（ｃｌｏｐｒｏｐ）、クロルメコート（ｃｈｌｏｒｍｅｑｕａｔ）、コリン（ｃｈｏｌｉｎｅ）、サイトカイニン（ｃｙｔｏｋｉｎｉｎｓ）、シクラニリド（ｃｙｃｌａｎｉｌｉｄｅ）、ジケグラック（ｄｉｋｅｇｕｌａｃ）、ジベレリン（ｇｉｂｂｅｒｅｌｌｉｎ　ａｃｉｄ）、ジメチピン（ｄｉｍｅｔｈｉｐｉｎ）、シントフェン（ｓｉｎｔｏｆｅｎ）、ダミノジット（ｄａｍｉｎｏｚｉｄｅ）、チジアズロン（ｔｈｉｄｉａｚｕｒｏｎ）、トリアコンタノール（ｔｒｉａｃｏｎｔａｎｏｌ）、トリネキサパック・エチル（ｔｒｉｎｅｘａｐａｃ－ｅｔｈｙｌ）、パクロブトラゾール（ｐａｃｌｏｂｕｔｒａｚｏｌ）、パラフィン（ｐａｒａｆｆｉｎ）、フルメトラリン（ｆｌｕｍｅｔｒａｌｉｎ）、フルルプリミドール（ｆｌｕｒｐｒｉｍｉｄｏｌ）、フルレノール（ｆｌｕｒｅｎｏｌ）、プロニトリジン（ｐｒｏｎｉｔｒｉｄｉｎｅ）、プロヒドロジャスモン（ｐｒｏｈｙｄｒｏｊａｓｍｏｎ）、プロヘキサジオン・カルシウム塩（ｐｒｏｈｅｘａｄｉｏｎｅ－ｃａｌｃｉｕｍ）、ヘプタマロキシログルカン（ｈｅｐｔａｍａｌｏｘｙｌｏｇｌｕｃａｎ）、ベンジルアミノプリン（ｂｅｎｚｙｌａｍｉｎｏｐｕｒｉｎｅ）、ホルクロルフェニュロン（ｆｏｒｃｈｌｏｒｆｅｎｕｒｏｎ）、マレイン酸ヒドラジド（ｍａｌｅｉｃ　ｈｙｄｒａｚｉｄｅ）、メピコート・クロリド（ｍｅｐｉｑｕａｔ　ｃｈｌｏｒｉｄｅ）、メフルイジド（ｍｅｆｌｕｉｄｉｄｅ）、過酸化カルシウム。 Plant growth regulator:
1-naphthylacetamide, 1-methylcyclopropene, 2,6-diisopropylnaphthalene, 2, oxo-4- (2-phenylethyl) aminobutyric acid, Chemical name, CAS registry number: 1083-55-2), 4-chlorophenoxyacetic acid (4-CPA), n-decyl alcohol (n-decanol), aviglycine, ancymidol, abscisic acid ( abscisic acid, inabenfide, indole acetic acid, indole butyric acid (indole butyric acid) id), uniconazole, uniconazole-P, unicozole-P, ecolist, ethiclozate, ethephon, ethephon, epocholeone, oxine sulfate, oxine sulfate ), Calcium formate (calcium formate), cloxyfonac (cloxyfonac), cloxyfonac-potassium salt (cloxyfonac-potassium), cloprop (chlorprop), chlormequat (chlormequat), choline (cinoclinine), cytokinincin (cincindinine) (Cyclanilide) Dikegulac, gibberellin acid, dimethipin, sintofen, daminozide, thiaziazuron, triacontanol, ethyl, triacontanolexanol Lobutrazole, paraffin, parametrin, flumetralin, flurprimidol, flurenol, pronitridine, pronitridine, prohydrojasimon diprohexa dipromonas Prohexadione-calcium, heptamaloxyloglucan, benzylaminopurine, forchlorfenuron, maleic acid hydrazide, maleic hydridide, maleic hydridide, maleic hydridide, maleic hydridide, maleic hydridide, maleic hydridide mefluid), calcium peroxide.
　次に、混合又は併用してもよい公知の薬害軽減化合物を例示する。 Next, known compounds for reducing harmful effects which may be mixed or used in combination are exemplified.
　イソキサジフェン（ｉｓｏｘａｄｉｆｅｎ）、イソキサジフェン－エチル（ｉｓｏｘａｄｉｆｅｎ－ｅｔｈｙｌ）、オキサベトリニル（ｏｘａｂｅｔｒｉｎｉｌ）、クロキントセット－メキシル（ｃｌｏｑｕｉｎｔｃｅｔ－ｍｅｘｙｌ）、ジエトレート（ｄｉｅｔｈｏｌａｔｅ）、シオメトリニル（ｃｙｏｍｅｔｒｉｎｉｌ）、ジクロルミド（ｄｉｃｈｌｏｒｍｉｄ）、ジシクロノン（ｄｉｃｙｃｌｏｎｏｎｅ）、シプロスルファミド（ｃｙｐｒｏｓｕｌｆａｍｉｄｅ）、ナフタル酸無水物（１，８－Ｎａｐｈｔｈａｌｉｃ　Ａｎｈｙｄｒｉｄｅ）、フェンクロラゾール－エチル（ｆｅｎｃｈｌｏｒａｚｏｌｅ－Ｏ－ｅｔｈｙｌ）、フェンクロリム（ｆｅｎｃｌｏｒｉｍ）、フリラゾール（ｆｕｒｉｌａｚｏｌｅ）、フルキソフェニム（ｆｌｕｘｏｆｅｎｉｍ）、フルラゾール（ｆｌｕｒａｚｏｌｅ）、ベノキサコル（ｂｅｎｏｘａｃｏｒ）、メフェネート（ｍｅｐｈｅｎａｔｅ）、メフェンピル（ｍｅｆｅｎｐｙｒ）、メフェンピルエチル（ｍｅｆｅｎｐｙｒ－ｅｔｈｙｌ）、メフェンピル－ジエチル（ｍｅｆｅｎｐｙｒ－ｄｉｅｔｈｙｌ）、低級アルキル置換安息香酸、２，２－ジクロロ－Ｎ－（１，３－ジオキサン－２－イルメチル）－Ｎ－（２－プロペニル）アセトアミド（ＰＰＧ－１２９２）、２－ジクロロメチル－２－メチル－１，３－ジオキサン（ＭＧ－１９１）、３－ジクロロアセチル－２，２，５－トリメチル－１，３－オキサゾリジン（Ｒ－２９１４８）、４－ジクロロアセチル－１－オキサ－４－アザスピロ［４．５］デカン（ＡＤ－６７）、ＭＯＮ４６６０（コード番号）、メトカミフェン（ｍｅｔｃａｍｉｆｅｎ）、Ｎ１，Ｎ２－ジアリル－Ｎ２－ジクロロアセチルグリシンアミド（ＤＫＡ－２４）、ＴＩ－３５（コード番号）。 Isoxadifen, isoxadifen-ethyl, oxabetrinil, cloquintcet-mexyl, dietholate, dimethoate, dimethoate Cyprosulfamide, naphthalic anhydride (1,8-Naphthalic @ Anhydride), fenchlorazole-O-ethyl, fenchlorim, furilazole, furixazole uxofenim), flurazole, benoxacor, mephenate, mefenpyr, mefenpyr-ethyl, mefenpyr-diethyl, mefenpyr-diethyl, lower alkyl, substituted lower alkyl, mefenpyr-diethyl 2-dichloro-N- (1,3-dioxan-2-ylmethyl) -N- (2-propenyl) acetamide (PPG-1292), 2-dichloromethyl-2-methyl-1,3-dioxane (MG-191) ), 3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine (R-29148), 4-dichloroacetyl-1-oxa-4-azaspiro [4.5] decane (AD-67), MON46 0 (code number), Metokamifen (metcamifen), N1, N2- diallyl -N2- dichloroacetyl glycinamide (DKA-24), TI-35 (code number).
　以上のように構成される本発明の有害生物防除剤は、バッタ目害虫、アザミウマ目害虫、カメムシ目害虫、コウチュウ目害虫、ハエ目害虫、チョウ目害虫、ハチ目害虫、トビムシ目害虫、シミ目害虫、ゴキブリ目害虫、チャタテムシ目害虫、ハジラミ目害虫、シラミ目害虫、植物寄生性ダニ類、植物寄生性線虫類、植物寄生性軟体動物、その他の有害動物、不快動物、衛生害虫、寄生虫等の有害生物に対して、優れた防除効果を示す。そのような有害生物としては、以下のような生物種を例示することができる。 The pest control agent of the present invention configured as described above includes grasshopper pests, thrips pests, stinkbug pests, crustacean pests, fly eye pests, lepidopteran pests, wasp order pests, coleoptera, pests Pests, cockroach pests, chapterae pests, whiteflies pests, lice pests, plant parasitic mites, plant parasitic nematodes, plant parasitic molluscs, other pests, unpleasant animals, sanitary pests, parasites It has an excellent control effect against pests such as Examples of such pests include the following species.
　バッタ目害虫としては、例えば、キリギリス科のクサキリ（Ｒｕｓｐｏｌｉａ　ｌｉｎｅｏｓａ）等、コオロギ科のエンマコオロギ（Ｔｅｌｅｏｇｒｙｌｌｕｓ　ｅｍｍａ）、アオマツムシ（Ｔｒｕｌｊａｌｉａ　ｈｉｂｉｎｏｎｉｓ）等、ケラ科のケラ（Ｇｒｙｌｌｏｔａｌｐａ　ｏｒｉｅｎｔａｌｉｓ）、バッタ科のコバネイナゴ（Ｏｘｙａ　ｈｙｌａ　ｉｎｔｒｉｃａｔｅ）、トノサマバッタ（Ｌｏｃｕｓｔａ　ｍｉｇｒａｔｏｒｉａ）、マイグラトリーグラスホッパー（Ｍｅｌａｎｏｐｌｕｓ　ｓａｎｇｕｉｎｉｐｅｓ）、ディファレンシャルグラスホッパー（Ｍｅｌａｎｏｐｌｕｓ　ｄｉｆｆｅｒｅｎｔｉａｌｉｓ）、レッドレッグドグラスホッパー（Ｍｅｌａｎｏｐｌｕｓ　ｆｅｍｕｒｒｕｂｒｕｍ）等、オンブバッタ科のオンブバッタ（Ａｔｒａｃｔｏｍｏｒｐｈａ　ｌａｔａ）、マツムシ科のカヤコオロギ（Ｅｕｓｃｙｒｔｕｓ　ｊａｐｏｎｉｃｕｓ）、ノミバッタ科のノミバッタ（Ｘｙａ　ｊａｐｏｎｉｃｕｓ）等を挙げることができる。 Examples of the grasshopper pests include, for example, Ruspolia lineeosa of the family Grassicaceae, emerma crickets of the cricket family (Teleogrylus emma), and green worms (Truljalia hibinoni of the family Keragina (Galina), such as Kera (Galenta pallidae). intricate), Tososama grasshopper (Locusta @ migratoria), Migratry grasshopper (Melanoplus @ sanguinipes), Differential grasshopper (Melanoplus @ diferentialis), Red-legged grasshopper (Melanophuraumurus, Melanopuras, etc.) Bubatta (Atractomorpha lata), Kayakoorogi (Euscyrtus japonicus) of pine cricket family, mention may be made of the Nomibatta of Nomibatta Department (Xya japonicus) and the like.
　アザミウマ目害虫としては、例えば、アザミウマ科のヒラズハナアザミウマ（Ｆｒａｎｋｌｉｎｉｅｌｌａ　ｉｎｔｏｎｓａ）、ミカンキイロアザミウマ（Ｆｒａｎｋｌｉｎｉｅｌｌａ　ｏｃｃｉｄｅｎｔａｌｉｓ）、チャノキイロアザミウマ（Ｓｃｉｒｔｏｔｈｒｉｐｓ　ｄｏｒｓａｌｉｓ）、ミナミキイロアザミウマ（Ｔｈｒｉｐｓ　ｐａｌｍｉ）、ネギアザミウマ（Ｔｈｒｉｐｓ　ｔａｂａｃｉ）、ダイズウスイロアザミウマ（Ｔｈｒｉｐｓ　ｓｅｔｏｓｕｓ）、クロトンアザミウマ（Ｈｅｌｉｏｔｈｒｉｐｓ　ｈａｅｍｏｒｒｈｏｉｄａｌｉｓ）、イネアザミウマ（Ｓｔｅｎｃｈａｅｔｏｔｈｒｉｐｓ　ｂｉｆｏｒｍｉｓ）等、クダアザミウマ科のカキクダアザミウマ（Ｐｏｎｔｉｃｕｌｏｔｈｒｉｐｓ　ｄｉｏｓｐｙｒｏｓｉ）、ワサビクダアザミウマ（Ｌｉｏｔｈｒｉｐｓ　ｗａｓａｂｉａｅ）、イネクダアザミウマ（Ｈａｐｌｏｔｈｒｉｐｓ　ａｃｕｌｅａｔｕｓ）等を挙げることができる。 The Thysanoptera, for example, of the thrips family Hirazuhanaazamiuma (Frankliniella intonsa), western flower thrips (Frankliniella occidentalis), yellow tea thrips (Scirtothrips dorsalis), southern thrips (Thrips palmi), green onion thrips (Thrips tabaci), Daizuusu Thrips thrips (Thrips @ setosus), Croton thrips (Heliothrips @ haemorrhoidalis), Rice thrips (Stenchaethotrips @ biformis), etc., of the family Thrips thrips (Thrips thrips). Wasabi Kuda thrips (Liothrips wasabiae), rice Kedah thrips (Haplothrips aculeatus), and the like can be given.
　カメムシ目害虫としては、例えば、セミ科のイワサキクサゼミ（Ｍｏｇａｎｎｉａ　ｍｉｎｕｔａ）等、アワフキムシ科のシロオビアワフキ（Ａｐｈｒｏｐｈｏｒａ　ｉｎｔｅｒｍｅｄｉａ）、シュガーケーンスピットルバグ（Ｍａｈａｎａｒｖａ　ｆｉｍｂｒｉｏｌａｔａ）等、ツノゼミ科のトビイロツノゼミ（Ｍａｃｈａｅｒｏｔｙｐｕｓ　ｓｉｂｉｒｉｃｕｓ）等、ヨコバイ科のフタテンヒメヨコバイ（Ａｒｂｏｒｉｄｉａ　ａｐｉｃａｌｉｓ）、チャノミドリヒメヨコバイ（Ｅｍｐｏａｓｃａ　ｏｎｕｋｉｉ）、ツマグロヨコバイ（Ｎｅｐｈｏｔｅｔｔｉｘ　ｃｉｎｃｔｉｃｅｐｓ）、マラヤツマグロヨコバイ（Ｎｅｐｈｏｔｅｔｔｉｘ　ｍａｌａｙａｎｕｓ）、タイワンツマグロヨコバイ（Ｎｅｐｈｏｔｅｔｔｉｘ　ｖｉｒｅｓｃｅｎｓ）、クロスジツマグロヨコバイ（Ｎｅｐｈｏｔｅｔｔｉｘ　ｎｉｇｒｏｐｉｃｔｕｓ）、イナズマヨコバイ（Ｒｅｃｉｌｉａ　ｄｏｒｓａｌｉｓ）、オクラリーフホッパー（Ａｍｒａｓｃａ　ｂｉｇｕｔｔｕｌａ）、マンゴーリーフホッパー（Ｉｄｉｏｓｃｏｐｕｓ　ｎｉｔｉｄｕｌｕｓ、Ｉｄｉｏｓｃｏｐｕｓ　ｃｌｙｐｅａｌｉｓ、Ａｍｒｉｔｏｄｕｓ　ａｔｋｉｎｓｏｎｉ）、イナズマヨコバイ（Ｒｅｃｉｌｉａ　ｄｏｒｓａｌｉｓ）、ポテトリーフホッパー（Ｅｍｐｏａｓｃａ　ｆａｂａｅ）、コーンリーフホッパー（Ｄａｌｂｕｌｕｓ　ｍａｉｄｉｓ）等、ヒシウンカ科のヒシウンカ（Ｐｅｎｔａｓｔｉｒｉｄｉｕｓ　ａｐｉｃａｌｉｓ）等、ウンカ科のヒメトビウンカ（Ｌａｏｄｅｌｐｈａｘ　ｓｔｒｉａｔｅｌｌｕｓ）、トビイロウンカ（Ｎｉｌａｐａｒｖａｔａ　ｌｕｇｅｎｓ）、セジロウンカ（Ｓｏｇａｔｅｌｌａ　ｆｕｒｃｉｆｅｒａ）、トウモロコシウンカ（Ｐｅｒｅｇｒｉｎｕｓ　ｍａｉｄｉｓ）等、シマウンカ科のシマウンカ（Ｎｉｓｉａ　ｎｅｒｖｏｓａ）等、ハネナガウンカ科のサトウマダラウンカ（Ｋａｍｅｎｄａｋａ　ｓａｃｃｈａｒｉｖｏｒａ）等、コガラシウンカ科のレッドファンガスバック（Ａｃｈｉｌｕｓ　ｆｌａｍｍｅｕｓ）等、ハゴロモ科のベッコウハゴロモ（Ｏｒｏｓａｎｇａ　ｊａｐｏｎｉｃｕｓ）等、アオバハゴロモ科のトビイロハゴロモ（Ｍｉｍｏｐｈａｎｔｉａ　ｍａｒｉｔｉｍａ）等、キジラミ科のナシキジラミ（Ｃａｃｏｐｓｙｌｌａ　ｐｙｒｉｓｕｇａ）、ミカンキジラミ（Ｄｉａｐｈｏｒｉｎａ　ｃｉｔｒｉ）等、ヒメキジラミ科のマンゴーキジラミ（Ｃａｌｏｐｈｙａ　ｍａｎｇｉｆｅｒａｅ）等、フィロキセラ科のブドウネアブラムシ（Ｄａｋｔｕｌｏｓｐｈａｉｒａ　ｖｉｔｉｆｏｌｉａｅ）等、カサアブラムシ科のカラマツカサアブラムシ（Ａｄｅｌｇｅｓ　ｌａｒｉｃｉｓ）、ハリモミヒノカサアブラムシ（Ａｄｅｌｇｅｓ　ｔｓｕｇａｅ）等、アブラムシ科のエンドウヒゲナガアブラムシ（Ａｃｙｒｔｈｏｓｉｐｈｏｎ　ｐｉｓｕｍ）、ワタアブラムシ（Ａｐｈｉｓ　ｇｏｓｓｙｐｉｉ）、ユキヤナギアブラムシ（Ａｐｈｉｓ　ｓｐｉｒａｅｃｏｌａ）、ニセダイコンアブラムシ（Ｌｉｐａｐｈｉｓ　ｅｒｙｓｉｍｉ）、ダイコンアブラムシ（Ｂｒｅｖｉｃｏｒｙｎｅ　ｂｒａｓｓｉｃａｅ）、モモアカアブラムシ（Ｍｙｚｕｓ　ｐｅｒｓｉｃａｅ）、ムギミドリアブラムシ（Ｓｃｈｉｚａｐｈｉｓ　ｇｒａｍｉｎｕｍ）、ムギクビレアブラムシ（Ｒｈｏｐａｌｏｓｉｐｈｕｍ　ｐａｄｉ）、コミカンアブラムシ（Ｔｏｘｏｐｔｅｒａ　ａｕｒａｕｔｉｉ）、ジャガイモヒゲナガアブラムシ（Ａｕｌａｃｏｒｔｈｕｍ　ｓｏｌａｎｉ）、チューリップヒゲナガアブラムシ（Ｍａｃｒｏｓｉｐｈｕｍ　ｅｕｐｈｏｒｂｉａｅ）、キュラントレタスアフィッド（Ｎａｓｏｎｏｖｉａ　ｒｉｂｉｓｎｉｇｒｉ）、イングリッシュグレインアフィッド（Ｓｉｔｏｂｉｏｎ　ａｖｅｎａｅ）、ソイビーンアフィッド（Ａｐｈｉｓ　ｇｌｙｃｉｎｅｓ）等、コナジラミ科のチャトゲコナジラミ（Ａｌｅｕｒｏｃａｎｔｈｕｓ　ｃａｍｅｌｌｉａｅ）、ミカントゲコナジラミ（Ａｌｅｕｒｏｃａｎｔｈｕｓ　ｓｐｉｎｉｆｅｒｕｓ）、タバココナジラミ（Ｂｅｍｉｓｉａ　ｔａｂａｃｉ）、シルバーリーフコナジラミ（Ｂｅｍｉｓｉａ　ａｒｇｅｎｔｉｆｏｌｉｉ）、オンシツコナジラミ（Ｔｒｉａｌｅｕｒｏｄｅｓ　ｖａｐｏｒａｒｉｏｒｕｍ）等、ワタフキカイガラムシ科のオオワラジカイガラムシ（Ｄｒｏｓｉｃｈａ　ｃｏｒｐｕｌｅｎｔａ）、イセリアカイガラムシ（Ｉｃｅｒｙａ　ｐｕｒｃｈａｓｉ）等、コナカイガラムシ科のパイナップルコナカイガラムシ（Ｄｙｓｍｉｃｏｃｃｕｓ　ｂｒｅｖｉｐｅｓ）、ミカンコナカイガラムシ（Ｐｌａｎｏｃｏｃｃｕｓ　ｃｉｔｒｉ）、クワコナカイガラムシ（Ｐｓｅｕｄｏｃｏｃｃｕｓ　ｃｏｍｓｔｏｃｋｉ）等、カタカイガラムシ科のツノロウムシ（Ｃｅｒｏｐｌａｓｔｅｓ　ｃｅｒｉｆｅｒｕｓ）、ルビーロウムシ（Ｃｅｒｏｐｌａｓｔｅｓ　ｒｕｂｅｎｓ）等、カタカイガラモドキ科のカンシャカタカイガラモドキ（Ａｃｌｅｒｄａ　ｔａｋａｈａｓｈｉｉ）等、マルカイガラムシ科のアカマルカイガラムシ（Ａｏｎｉｄｉｅｌｌａ　ａｕｒａｎｔｉｉ）、ナシマルカイガラムシ（Ｄｉａｓｐｉｄｉｏｔｕｓ　ｐｅｒｎｉｃｉｏｓｕｓ）、クワシロカイガラムシ（Ｐｓｅｕｄａｕｌａｃａｓｐｉｓ　ｐｅｎｔａｇｏａ）、ヤノネカイガラムシ（Ｕｎａｓｐｉｓ　ｙａｎｏｎｅｎｓｉｓ）等、カスミカメムシ科のターニッシュドプラントバグ（Ｌｙｇｕｓ　ｌｉｎｅｏｌａｒｉｓ）、アカヒゲホソミドリカスミカメ（Ｔｒｉｇｏｎｏｔｙｌｕｓ　ｃａｅｌｅｓｔｉａｌｉｕｍ）、コアオカスミカメ（Ａｐｏｌｙｇｕｓ　ｌｕｃｏｒｕｍ）、タバコカスミカメ（Ｎｅｓｉｄｉｏｃｏｒｉｓ　ｔｅｎｕｉｓ）、ガーデンフレアホッパー（Ｈａｌｔｉｃｕｓ　ｂｒａｃｔａｔｕｓ）等、グンバイムシ科のツツジグンバイ（Ｓｔｅｐｈａｎｉｔｉｓ　ｐｙｒｉｏｉｄｅｓ）、ナシグンバイ（Ｓｔｅｐｈａｎｉｔｉｓ　ｎａｓｈｉ）等、カメムシ科のナガメ（Ｅｕｒｙｄｅｍａ　ｒｕｇｏｓｕｍ）、オオトゲシラホシカメムシ（Ｅｙｓａｒｃｏｒｉｓ　ｌｅｗｉｓｉ）、トゲシラホシカメムシ（Ｅｙｓａｒｃｏｒｉｓ　ａｅｎｅｕｓ）、イネカメムシ（Ｌａｇｙｎｏｔｏｍｕｓ　ｅｌｏｎｇａｔｕｓ）、ミナミアオカメムシ（Ｎｅｚａｒａ　ｖｉｒｉｄｕｌａ）、チャバネアオカメムシ（Ｐｌａｕｔｉａ　ｃｒｏｓｓｏｔａ）、アオクサカメムシ（Ｎｅｚａｒａ　ａｎｔｅｎｎａｔａ）、スティンクバグ（Ｅｕｓｈｉｓｔｕｓ　ｈｅｒｏｓ）、レッドバンデッドスティンクバグ（Ｐｉｅｚｏｄｏｒｕｓ　ｇｕｉｌｄｉｎｉ）、ライススティンクバグ（Ｔｉｂｒａｃａ　ｌｉｍｂａｔｉｖｅｎｔｒｉｓ）、グリーンベリースティンクバグ（Ｄｉｃｈｅｌｏｐｓ　ｆｕｒｃａｔｕｓ）等、マルカメムシ科のタイワンマルカメムシ（Ｍｅｇａｃｏｐｔａ　ｃｒｉｂｒａｒｉａ）等、クヌギカメムシ科のナシカメムシ（Ｕｒｏｃｈｅｌａ　ｌｕｔｅｏｖｏｒｉａ）等、ナガカメムシ科のカンシャコバネナガカメムシ（Ｃａｖｅｌｅｒｉｕｓ　ｓａｃｃｈａｒｉｖｏｒｕｓ）等、メダカナガカメムシ科のオオメダカナガカメムシ（Ｍａｌｃｕｓ　ｊａｐｏｎｉｃｕｓ）等、ホシカメムシ科のアカホシカメムシ（Ｄｙｓｄｅｒｃｕｓ　ｃｉｎｇｕｌａｔｕｓ）等、ホソヘリカメムシ科のホソクモヘリカメムシ（Ｌｅｐｔｏｃｏｒｉｓａ　ａｃｕｔａ）、クモヘリカメムシ（Ｌｅｐｔｏｃｏｒｉｓａ　ｃｈｉｎｅｎｓｉｓ）等、ヘリカメムシ科のオオクモヘリカメムシ（Ａｎａｃａｎｔｈｏｃｏｒｉｓ　ｓｔｒｉｉｃｏｒｎｉｓ）等、ヒメヘリカメムシ科のアカヒメヘリカメムシ（Ｒｈｏｐａｌｕｓ　ｍａｃｕｌａｔｕｓ）等、ツチカメムシ科のバロワーブラウンスティンクバグ（Ｓｃａｐｔｏｃｏｒｉｓ　ｃａｓｔａｎｅａ）等、トコジラミ科のトコジラミ（Ｃｉｍｅｘ　ｌｅｃｔｕｌａｒｉｓ）等を挙げることができる。 Examples of the stink bug pests include, for example, the cicada family, Iwaki-kami-semi (Mogannia @ minuta), the Aphid beetle family (Aphrophora @ intermedia), the sugarcane spitbug (Mahanarva @ fimbriata, and the like), and the like. Leafhoppers of the leafhopper family (Arbordia @ apicalis), Leafhoppers (Empoasca @ onukii), Leafhoppers (Nephotettix @ cincticeps), and Leafhopper Leafhoppers (Nephotettix) ens), cross di leafhopper (Nephotettix nigropictus), Inazuma leafhopper (Recilia dorsalis), okra leaf hopper (Amrasca biguttula), mango leaf hopper (Idioscopus nitidulus, Idioscopus clypealis, Amritodus atkinsoni), Inazuma leafhopper (Recilia dorsalis), potato leaf hopper (Empoasca @ fabae), corn leaf hoppers (Dalbulus @ maidis), etc., and the brown planthopper (Pentastiridius @ apicalis), etc. And the family of the family Carnidae (Nissia acer), such as the family of the family Siracusa (Nissia), and the family of the family of the family Siracusa (Ricaceae), Bacillus serrata (Achirus @ flammeus), etc., Orosanga @ japonicus, etc., Aobahagoromo family, etc., Mimophantia @ maritima, etc .; ri) and others; Calophya mangiferae of the family Lamiaceae; Daktulosphaira vitifoliae of the family Philoxera; In the families, Aphirosiphon apisum, Aphis gossypii, Aphis gossypii, Aphis spiraecola, Aphid aphisii, Aphis mosaic blossoms ersicae), wheat midge aphid (Schizzaphis @ graminum), wheat aphid (Rhopalosiphum @ padi), citrus aphid (Toxoptera @ aurautii), potato beetle (Aulacorthium aphium) Nasoniavia rivisnigri, English grain affine (Sitobion avenenae), soybean affine (Aphis @ glycines), etc., of the family Whitefly (Aleurocanthus camellia) ocanthus spiniferus), tobacco whitefly (Bemisia tabaci), silverleaf whitefly (Bemisia argentifolii), greenhouse whitefly (Trialeurodes vaporariorum), etc., giant straw sandals scale insects (Drosicha corpulenta of cotton butterbur scale insects family), Iseria scale insects (Icerya purchasi), etc., mealybug Department Pineapple beetle (Dysmicoccus brevipes), orange pine beetle (Planococcus citri), mulberry beetle (Pseudococcus comstocki), etc. es ceriferus, ruby beetle (Ceroplastes rubens), etc .; pentagoa), Unaspis @ yanonensis, etc., Turned plant bugs (Lygus @ lineolaris) of the family Staphylinidae, Trigonotoylus @ caelestiariaum, and koa okasomime. gus lucorum, Nesidiocoris tenuis, garden flare hopper (Halticus bractatas), etc .; (Eysarcoris @ lewisi), Scarlet beetle (Eysarcoris @ aeneus), Rice stink bug (Lagynotomus @ elongatus), southern stink bug (Nezar @ viridae mosquitoes) Anthracidae from the family of the sect. Marica Memba et al. (Urochela luteovoria), etc. of the family Scarabaeidae; Yersdercus singulatus, etc .; Leptocorisa acuta of the family Leptococci; Leptocorisa chinensis; Examples include the stink bug (Rhopalus maculatus), the lower bug stink bug (Scaptocoris @ castanea), the bed bug (Cimex @ lectularis), and the like.
　コウチュウ目害虫としては、例えば、コガネムシ科のドウガネブイブイ（Ａｎｏｍａｒａ　ｃｕｐｒｅａ）、ヒメコガネ（Ａｎｏｍａｒａ　ｒｕｆｏｃｕｐｒｅａ）、マメコガネ（Ｐｏｐｉｌｌｉａ　ｊａｐｏｎｉｃａ）、コアオハナムグリ（Ｏｘｙｃｅｔｏｎｉａ　ｊｕｃｕｎｄａ）、サクラコガネ（Ａｎｏｍａｌａ　ｇｅｎｉｃｕｌａｔａ）、サイカブトムシ（Ｏｒｙｃｔｅｓ　ｒｈｉｎｏｃｅｒｏｓ）、ナガチャコガネ（Ｈｅｐｔｏｐｈｙｌｌａ　ｐｉｃｅａ）、フィロファガクヤバナ（Ｐｈｙｌｌｏｐｈａｇａ　ｃｕｙａｂａｎａ）等、コメツキムシ科のトビイロムナボソコメツキ（Ａｇｒｉｏｔｅｓ　ｏｇｕｒａｅ）、アグリオテスリネアツス（Ａｇｒｉｏｔｅｓ　ｌｉｎｅａｔｕｓ）、アグリオテスオブスクルス（Ａｇｒｉｏｔｅｓ　ｏｂｓｃｕｒｕｓ）、オキナワカンシャクシコメツキ（Ｍｅｌａｎｏｔｕｓ　ｏｋｉｎａｗｅｎｓｉｓ）、マルクビクシコメツキ（Ｍｅｌａｎｏｔｕｓ　ｆｏｒｔｎｕｍｉ）等、カツオブシムシ科のヒメマルカツオブシムシ（Ａｎｔｈｒｅｎｕｓ　ｖｅｒｂａｓｃｉ）等、ナガシンクイムシ科のオオナガシンクイムシ（Ｈｅｔｅｒｏｂｏｓｔｒｙｃｈｕｓ　ｈａｍａｔｉｐｅｎｎｉｓ）等、シバンムシ科のジンサンシバンムシ（Ｓｔｅｇｏｂｉｕｍ　ｐａｎｉｃｅｕｍ）等、ヒョウホンムシ科のヒメヒョウホンムシ（Ｐｉｔｉｎｕｓ　ｃｌａｖｉｐｅｓ）等、コクヌスト科のコクヌスト（Ｔｅｎｅｂｒｏｉｄｅｓ　ｍａｕｒｉｔａｎｉｃｕｓ）等、カッコウムシ科のアカアシホシカムシ（Ｎｅｃｒｏｂｉａ　ｒｕｆｉｐｅｓ）、ケシキスイ科のクリヤケシキスイ（Ｃａｒｐｏｐｈｉｌｕｓ　ｈｅｍｉｐｔｅｒｕｓ）、ポーレンビートル（Ｍｅｌｉｇｅｔｈｅｓ　ａｅｎｅｕｓ）等、ホソヒラタムシ科のカブコブホソヒラタムシ（Ａｈａｓｖｅｒｕｓ　ａｄｖｅｎａ）等、チビヒラタムシ科のサビカクムネヒラタムシ（Ｃｒｙｐｔｏｌｅｓｔｅｓ　ｆｅｒｒｕｇｉｎｅｕｓ）等、テントウムシ科のインゲンテントウ（Ｅｐｉｌａｃｈｎａ　ｖａｒｉｖｅｓｔｉｓ）、ニジュウヤホシテントウ（Ｈｅｎｏｓｅｐｉｌａｃｈｎａ　ｖｉｇｉｎｔｉｏｃｔｏｐｕｎｃｔａｔａ）等、ゴミムシダマシ科のチャイロコメノゴミムシダマシ（Ｔｅｎｅｂｒｉｏ　ｍｏｌｉｔｏｒ）、コクヌストモドキ（Ｔｒｉｂｏｌｉｕｍ　ｃａｓｔａｎｅｕｍ）等、ツチハンミョウ科のマメハンミョウ（Ｅｐｉｃａｕｔａ　ｇｏｒｈａｍｉ）等、カミキリムシ科のツヤハダゴマダラカミキリ（Ａｎｏｐｌｏｐｈｏｒａ　ｇｌａｂｒｉｐｅｎｎｉｓ）、ブドウトラカミキリ（Ｘｙｌｏｔｒｅｃｈｕｓ　ｐｙｒｒｈｏｄｅｒｕｓ）、マツノマダラカミキリ（Ｍｏｎｏｃｈａｍｕｓ　ａｌｔｅｒｎａｔｕｓ）、ソイビーンステムボーラー（Ｄｅｃｔｅｓ　ｔｅｘａｎｕｓ）等、マメゾウムシ科のアズキゾウムシ（Ｃａｌｌｏｓｏｂｒｕｃｈｕｓ　ｃｈｉｎｅｎｓｉｓ）等、ハムシ科のコロラドハムシ（Ｌｅｐｔｉｎｏｔａｒｓａ　ｄｅｃｅｍｌｉｎｅａｔａ）、ウェスタンコーンルートワーム（Ｄｉａｂｒｏｔｉｃａ　ｖｉｒｇｉｆｅｒａ　ｖｉｒｇｉｆｅｒａ）、ノーザンコーンルートワーム（Ｄｉａｂｒｏｔｉｃａ　ｂａｒｂｅｒｉ）、サザンコーンルートワーム（Ｄｉａｂｒｏｔｉｃａ　ｕｎｄｅｃｉｍｐｕｎｃｔａｔａ　ｈｏｗａｒｄｉ）、ウリハムシ（Ａｕｌａｃｏｐｈｏｒａ　ｆｅｍｏｒａｌｉｓ）、ダイコンハムシ（Ｐｈａｅｄｏｎ　ｂｒａｓｓｉｃａｅ）、カメノコハムシ（Ｃａｓｓｉｄａ　ｎｅｂｕｌｏｓａ）、イネドロオイムシ（Ｏｕｌｅｍａ　ｏｒｙｚａｅ）、メキシカンビートル（Ｅｐｉｌａｃｈｎａ　ｖａｒｉｖｅｓｔｉｓ）、キスジノミハムシ（Ｐｈｙｌｌｏｔｒｅｔａ　ｓｔｒｉｏｌａｔａ）、マダラカサハラハムシ（Ｄｅｍｏｔｉｎａ　ｆａｓｃｉｃｕｌａｔａ）、キャベッジステムフレアビートル（Ｐｓｙｌｌｉｏｄｅｓ　ｃｈｒｙｓｏｃｅｐｈａｌａ）、ビーンリーフビートル（Ｃｅｒｏｔｏｍａ　ｔｒｉｆｕｒｃａｔｅ）、グレープコラスピス（Ｃｏｌａｓｐｉｓ　ｂｒｕｎｎｅａ）、アイオワコラスピス（Ｃｏｌａｓｐｉｓ　ｃｒｉｎｎｉｃｏｒｎｉｓ）、ソイビーンリーフマイナー（Ｏｄｏｎｔｏｔａ　ｈｏｒｎｉ）、コーンフレアビートル（Ｃｈａｅｔｏｃｎｅｍａ　ｐｕｌｉｃａｒｉａ）、バンデッドキューカンバービートル（Ｄｉａｂｒｏｔｉｃａ　ｂａｌｔｅａｔａ）等、ミツギリゾウムシ科のアリモドキゾウムシ（Ｃｙｌａｓ　ｆｏｒｍｉｃａｒｉｕｓ）等、ゾウムシ科のアルファルファタコゾウムシ（Ｈｙｐｅｒａ　ｐｏｓｔｉｃａ）、ヤサイゾウムシ（Ｌｉｓｔｒｏｄｅｒｅｓ　ｃｏｓｔｉｒｏｓｔｒｉｓ）、イモゾウムシ（Ｅｕｓｃｅｐｅｓ　ｐｏｓｔｆａｓｃｉａｔｕｓ）、クリシギゾウムシ（Ｃｕｒｃｕｌｉｏ　ｓｉｋｋｉｍｅｎｓｉｓ）、ワタミハナゾウムシ（Ａｎｔｈｏｎｏｍｕｓ　ｇｒａｎｄｉｓ）、ソイビーンストークウィービル（Ｓｔｅｒｎｅｃｈｕｓ　ｓｕｂｓｉｇｎａｔｕｓ）等、イネゾウムシ科のイネゾウムシ（Ｅｃｈｉｎｏｃｎｅｍｕｓ　ｂｉｐｕｎｃｔａｔｕｓ）、イネミズゾウムシ（Ｌｉｓｓｏｒｈｏｐｔｒｕｓ　ｏｒｙｚｏｐｈｉｌｕｓ）、サウスアメリカンライスウォーターウィービル（Ｏｒｙｚｏｐｈａｇｕｓ　ｏｒｙｚａｅ）等、オサゾウムシ科のコクゾウムシ（Ｓｉｔｏｐｈｉｌｕｓ　ｚｅａｍａｉｓ）、シバオサゾウムシ（Ｓｐｈｅｎｏｐｈｒｕｓ　ｖｅｎａｔｕｓ）、シュガーケーンウィービル（Ｓｐｈｅｎｏｐｈｏｒｕｓ　ｌｅｖｉｓ）等、キクイムシ科のマツノキクイムシ（Ｔｏｍｉｃｕｓ　ｐｉｎｉｐｅｒｄａ）等、ナガキクイムシ科のヤチダモノナガキクイムシ（Ｃｒｏｓｓｏｔａｒｓｕｓ　ｎｉｐｏｎｉｃｕｓ）等、ヒラタキクイムシ科のヒラタキクイムシ（Ｌｙｃｔｕｓ　ｂｒｕｎｎｅｕｓ）等を挙げることができる。 The Coleoptera, for example, cupreous chafer of Scarabaeidae (Anomara cuprea), rufocuprea (Anomara rufocuprea), Japanese beetle (Popillia japonica), core Oh flower chafer (Oxycetonia jucunda), Sakura Tsurukogane (Anomala geniculata), rhinoceros beetle (Oryctes rhinoceros) , (Heptophylla @ picea), Phyllophaga @ cuyabana, etc., of the family Beetle Beetle (Agriotes ogreas Aegeos ogreus). es obscurus, Okinawan sedge beetle (Melanotus kinawensis), ク ビ Ｍ (Melanotus ｔfortumi), etc .; Ginseng beetles (Stegobium paniceum) and the like, Lepidoptera beetles (Pitinus 等 clavipes) and the like, Kokunustaceous succulents (Tenebroides mauritanicus) and the like, and the cuckoo beetles (Akaashie shikoshibushikushi) and the cuckoo beetles (Akaeashi crocus focus). Cryptocarpium scrophleus in the family Cuboptera scents, such as Carpophilus hemipterus and Pollen beetle (Meligethes aeneus); Tentami (Epilachna @ varirivestis), T. japonica (Henosepilachna @ vigintioctopunctata), etc. of the Tenebrionidae family (Tenebrio molitor, etc.), etc. picauta gorhami), etc., Cerambycidae of the Asian long-horned beetle (Anoplophora glabripennis), grapes tiger beetle (Xylotrechus pyrrhoderus), Japanese pine sawyer (Monochamus alternatus), soybean stem borer (Dectes texanus), etc., adzuki bean weevil (Callosobruchus chinensis of bean weevils family), etc. , Leaf beetles Colorado potato beetle (Leptinotarsa decemlineata), Western corn root worm (Diabrotica virgifera virgifera), Northern corn root worm (Diabrotica barberi), Southern koa Rootworm (Diabrotica undecimpunctata howardi), cucurbit leaf beetle (Aulacophora femoralis), radish leaf beetle (Phaedon brassicae), Kamenokohamushi (Cassida nebulosa), Inedorooimushi (Oulema oryzae), Mexican beetle (Epilachna varivestis), Kisujinomihamushi (Phyllotreta striolata), Madara Kasahara beetle ( Demotina @ fasciculata, cabage stem flare beetle (Psyliodes @ chrysocephala), bean leaf beetle (Cerotoma @ trifurcate), grape colaspis (Co aspis brunnea), Iowa colspice (Colaspis crinnicornis), soybean leaf miner (Odontota horni), corn flare beetle (Chaetocnema pulicaria), banded cucumber beetle (Diabrotica zochia moss), etc. , Weevil weevil (Hypera @ postica), weevil (Listroderes @ costirostris), caterpillar (Euscepes @ postfasciatus), weevil weevil (Curculio @ sikkimensis), nthonomus grandis), soy bean stalk weevil (Sternechus subsignatus), etc., of the rice weevil family rice weevil (Echinocnemus bipunctatus), rice water weevil (Lissorhoptrus oryzophilus), South American rice water weevil (Oryzophagus oryzae), etc., of the weevil family grain weevil (Sitophilus zeamais), Sphenophilus venatus, Sugar Cane Weeville (Sphenophorus levis), etc., Bark Beetle (Tomicus ｉｎpiniperda), etc. Shi (Crossotarsus niponicus), etc., can be mentioned Hirata beetle family Hirata beetle (Lyctus brunneus) and the like.
　ハエ目害虫としては、例えば、ガガンボ科のキリウジガガンボ（Ｔｉｐｕｌａ　ａｉｎｏ）等、ケバエ科のラブバッグ（Ｐｌｅｃｉａ　ｎｅａｒｃｔｉｃａ）等、キノコバエ科のシイタケトンボキノコバエ（Ｅｘｅｃｈｉａ　ｓｈｉｉｔａｋｅｖｏｒａ）等、クロバネキノコバエ科のジャガイモクロバネキノコバエ（Ｐｎｙｘｉａ　ｓｃａｂｉｅｉ）、チビクロバネキノコバエ（Ｂｒａｄｙｓｉａ　ａｇｒｅｓｔｉｓ）等、タマバエ科のダイズサヤタマバエ（Ａｓｐｈｏｎｄｙｌｉａ　ｙｕｓｈｉｍａｉ）、ヘシアンバエ（Ｍａｙｅｔｉｏｌａ　ｄｅｓｔｒｕｃｔｏｒ）、ブルーベリータマバエ（Ｄａｓｉｎｅｕｒａ　ｏｘｙｃｏｃｃａｎａ）等、カ科のネッタイシマカ（Ａｅｄｅｓ　ａｅｇｙｐｔｉ）、アカイエカ（Ｃｕｌｅｘ　ｐｉｐｉｅｎｓ　ｐａｌｌｅｎｓ）等、ブユ科のウシブユ（Ｓｉｍｕｌｉｕｍ　ｔａｋａｈａｓｈｉｉ）等、ユスリカ科のイネユスリカ（Ｃｈｉｒｏｎｏｍｕｓ　ｏｒｙｚａｅ）等、アブ科のキンメアブ（Ｃｈｒｙｓｏｐｓ　ｓｕａｖｉｓ）、ウシアブ（Ｔａｂａｎｕｓ　ｔｒｉｇｏｎｕｓ）等、ハナアブ科のハイジマハナアブ（Ｅｕｍｅｒｕｓ　ｓｔｒｉｇａｔｕｓ）等、ミバエ科のミカンコミバエ（Ｂａｃｔｒｏｃｅｒａ　ｄｏｒｓａｌｉｓ）、オウトウハマダラミバエ（Ｅｕｐｈｒａｎｔａ　ｊａｐｏｎｉｃａ）、チチュウカイミバエ（Ｃｅｒａｔｉｔｉｓ　ｃａｐｉｔａｔａ）等、ハモグリバエ科のマメハモグリバエ（Ｌｉｒｉｏｍｙｚａ　ｔｒｉｆｏｌｉｉ）、トマトハモグリバエ（Ｌｉｒｉｏｍｙｚａ　ｓａｔｉｖａｅ）、イネハモグリバエ（Ａｇｒｏｍｙｚａ　ｏｒｙｚａｅ）、ナスハモグリバエ（Ｌｉｒｉｏｍｙｚａ　ｂｒｙｏｎｉａｅ）、ナモグリバエ（Ｃｈｒｏｍａｔｏｍｙｉａ　ｈｏｒｔｉｃｏｌａ）、ネギハモグリバエ（Ｌｉｒｉｏｍｙｚａ　ｃｈｉｎｅｎｓｉｓ）、アメリカンセルペンティンリーフマイナー（Ｌｉｒｉｏｍｙｚａ　ｔｒｉｆｏｌｉｉ）等、キモグリバエ科のムギキモグリバエ（Ｍｅｒｏｍｙｚａ　ｎｉｇｒｉｖｅｎｔｒｉｓ）等、ショウジョウバエ科のオウトウショウジョウバエ（Ｄｒｏｓｏｐｈｉｌａ　ｓｕｚｕｋｉｉ）、キイロショウジョウバエ（Ｄｒｏｓｏｐｈｉｌａ　ｍｅｌａｎｏｇａｓｔｅｒ）等、ミギワバエ科のイネミギワバエ（Ｈｙｄｒｅｌｌｉａ　ｇｒｉｓｅｏｌａ）等、シラミバエ科のウマシラミバエ（Ｈｉｐｐｏｂｏｓｃａ　ｅｑｕｉｎａ）等、フンバエ科のササカワフンバエ（Ｐａｒａｌｌｅｌｐｍｍａ　ｓａｓａｋａｗａｅ）等、ハナバエ科のタマネギバエ（Ｄｅｌｉａ　ａｎｔｉｑｕａ）、タネバエ（Ｄｅｌｉａ　ｐｌａｔｕｒａ）等、ヒメイエバエ科のヒメイエバエ（Ｆａｎｎｉａ　ｃａｎｉｃｕｌａｒｉｓ）等、イエバエ科のイエバエ（Ｍｕｓｃａ　ｄｏｍｅｓｔｉｃａ）、サシバエ（Ｓｔｏｍｏｘｙｓ　ｃａｌｃｉｔｒａｎｓ）等、ニクバエ科のセンチニクバエ（Ｓａｒｃｏｐｈａｇａ　ｐｅｒｅｇｒｉｎａ）等、ウマバエ科のウマバエ（Ｇａｓｔｅｒｏｐｈｉｌｕｓ　ｉｎｔｅｓｔｉｎａｌｉｓ）等、ウシバエ科のウシバエ（Ｈｙｐｏｄｅｒｍａ　ｌｉｎｅａｔｕｍ）等、ヒツジバエ科のヒツジバエ（Ｏｅｓｔｒｕｓ　ｏｖｉｓ）等を挙げることができる。 Examples of pests of the order Fly flies include, for example, the swordfish (Tipula aino) and the fly fly bag (Plecia nearctica) and the mushroom fly larva (Execia shiitakevora) and the mosquito scallop and the like. Bivalve mushrooms (Pnyxia scabiei), Blysia mushrooms (Bradysia agrestis), etc., soybean flies (Asphonylia yusimai), Hesian flies (Mayetiola マ ｓｔ 、 、 、 、 、 、 、 、 、 、 、 、 、 、) Culex pipiens (Culex @ pip ens @ pallens, etc .; Simulium @ takahashii, etc .; Chironomus @ oryzae, etc .; Afidae, Chrynobus @ suavis; ); Fly (Agromyza oryzae), eggplant leafminer (Liriomyza bryoniae), the pea (Chromatomyia horticola), green onion leafminer (Liriomyza chinensis), such as American cell pen Tin leaf minor (Liriomyza trifolii), Mugikimoguribae the chloropidae Department (Meromyza nigriventris) and the like, Drosophila Department Drosophila suzukii, Drosophila melanogaster, etc. of the family Dermatophagidae, Hydrelia ｒｉgriseola, etc. a equina, etc., the parasitidae (Parallepmma sasakawae), etc., the flies of the family Aniidae (Delia antiqua), the stalk fly (Delia platura), and the flies of the genus Musciidae (E. Stormfly (Stomoxys @ calcitrans), etc .; Sinophilidae (Sarcophaga @ peregrina), etc .; It can be.
　チョウ目害虫としては、例えば、コウモリガ科のコウモリガ（Ｅｎｄｏｃｌｉｔａ　ｅｘｃｒｅｓｃｅｎｓ）等、ツヤコガ科のブドウツヤコガ（Ａｎｔｉｓｐｉｌａ　ａｍｐｅｌｏｐｓｉａ）等、ボクトウガ科のゴマフボクトウ（Ｚｅｕｚｅｒａ　ｌｅｕｃｏｎｏｔｕｍ）、ヒメボクトウ（Ｃｏｓｓｕｓ　ｉｎｓｕｌａｒｉｓ）等、ハマキガ科のミダレカクモンハマキ（Ａｒｃｈｉｐｓ　ｆｕｓｃｏｃｕｐｒｅａｎｕｓ）、リンゴコカクモンハマキ（Ａｄｏｘｏｐｈｙｅｓ　ｏｒａｎａ　ｆａｓｃｉａｔａ）、ナシヒメシンクイ（Ｇｒａｐｈｏｌｉｔａ　ｍｏｌｅｓｔａ）、チャハマキ（Ｈｏｍｏｎａ　ｍａｇｎａｎｉｍａ）、マメシンクイガ（Ｌｅｇｕｍｉｎｉｖｏｒａ　ｇｌｙｃｉｎｉｖｏｒｅｌｌａ）、コドリンガ（Ｃｙｄｉａ　ｐｏｍｏｎｅｌｌａ）、ヨーロピアングレープバインモス（Ｌｏｂｅｓｉａ　ｂｏｔｒａｎａ）等、ホソハマキ科のブドウホソハマキ（Ｅｕｐｏｅｃｉｌｉａ　ａｍｂｉｇｕｅｌｌａ）等、ミノガ科のクロツヤミノガ（Ｂａｍｂａｌｉｎａ　ｓｐ．）、チャミノガ（Ｅｕｍｅｔａ　ｍｉｎｕｓｃｕｌａ）等、ヒロズコガ科のコクガ（Ｎｅｍａｐｏｇｏｎ　ｇｒａｎｅｌｌａ）、イガ（Ｔｉｎｅａ　ｔｒａｎｓｌｕｃｅｎｓ）等、チビガ科のナシチビガ（Ｂｕｃｃｕｌａｔｒｉｘ　ｐｙｒｉｖｏｒｅｌｌａ）等、ハモグリガ科のモモハモグリガ（Ｌｙｏｎｅｔｉａ　ｃｌｅｒｋｅｌｌａ）、ギンモンハモグリガ（Ｌｙｏｎｅｔｉａｐｒｕｎｉｆｏｌｉｅｌｌａ　ｍａｌｉｎｅｌｌａ）等、ホソガ科のチャノホソガ（Ｃａｌｏｐｔｉｌｉａ　ｔｈｅｉｖｏｒａ）、キンモンホソガ（Ｐｈｙｌｌｏｎｏｒｙｃｔｅｒ　ｒｉｎｇｏｎｉｅｌｌａ）等、コハモグリガ科のミカンハモグリガ（Ｐｈｙｌｌｏｃｎｉｓｔｉｓ　ｃｉｔｒｅｌｌａ）等、アトヒゲコガ科のネギコガ（Ａｃｒｏｌｅｐｉｏｐｓｉｓ　ｓａｐｐｏｒｅｎｓｉｓ）等、コナガ科ののコナガ（Ｐｌｕｔｅｌｌａ　ｘｙｌｏｓｔｅｌｌａ）、スガ科のリンゴスガ（Ｙｐｏｎｏｍｅｕｔａ　ｏｒｉｅｎｔａｌｉｓ）等、メムシガ科のリンゴヒメシンクイ（Ａｒｇｙｒｅｓｔｈｉａ　ｃｏｎｊｕｇｅｌｌａ）等、スカシバガ科のブドウスカシバ（Ｎｏｋｏｎａ　ｒｅｇａｌｉｓ）、コスカシバ（Ｓｙｎａｎｔｈｅｄｉｎ　ｈｅｃｔｏｒ）等、キバガ科のジャガイモガ（Ｐｈｔｈｏｒｉｍａｅａ　ｏｐｅｒｃｕｌｅｌｌａ）、バクガ（Ｓｉｔｏｔｒｏｇａ　ｃｅｒｅａｌｅｌｌａ）、ワタアカミムシガ（Ｐｅｃｔｉｎｏｐｈｏｒａ　ｇｏｓｓｙｐｉｅｌｌａ）、トマトリーフマイナー（Ｔｕｔａ　ａｂｓｏｌｕｔａ）等、シンクイガ科のモモシンクイガ（Ｃａｒｐｏｓｉｎａ　ｓａｓａｋｉｉ）等、マダラガ科のリンゴハマキクロバ（Ｉｌｌｉｂｅｒｉｓ　ｐｒｕｎｉ）等、イラガ科のイラガ（Ｍｏｎｅｍａ　ｆｌａｖｅｓｃｅｎｓ）等、ツトガ科のツトガ（Ａｎｃｙｌｏｌｏｍｉａ　ｊａｐｏｎｉｃａ）、ニカメイガ（Ｃｈｉｌｏ　ｓｕｐｐｒｅｓｓａｌｉｓ）、コブノメイガ（Ｃｎａｐｈａｌｏｃｒｏｃｉｓ　ｍｅｄｉｎａｌｉｓ）、アワノメイガ（Ｏｓｔｒｉｎｉａ　ｆｕｒｎａｃａｌｉｓ）、ハイマダラノメイガ（Ｈｅｌｌｕｌｌａ　ｕｎｄａｌｉｓ）、モモゴマダラメイガ（Ｃｏｎｏｇｅｔｈｅｓ　ｐｕｎｃｔｉｆｅｒｌｉｓ）、ワタヘリクロノメイガ（Ｄｉａｐｈａｎｉａ　ｉｎｄｉｃａ）、シバツトガ（Ｐａｒａｐｅｄｉａｓｉａ　ｔｅｔｅｒｒｅｌｌａ）、ヨーロピアンコーンボーラー（Ｏｓｔｒｉｎｉａ　ｎｕｂｉｌａｌｉｓ）等、シュガーケーンボーラー（Ｄｉａｔｒａｅａ　ｓａｃｃｈａｒａｌｉｓ）、メイガ科のスジマダラメイガ（Ｃａｄｒａ　ｃａｕｔｅｌｌａ）、ハチノスツヅリガ（Ｇａｌｌｅｒｉａ　ｍｅｌｌｏｎｅｌｌａ）等、トリバガ科のブドウトリバ（Ｎｉｐｐｏｐｔｉｌｉａ　ｖｉｔｉｓ）等、アゲハチョウ科のナミアゲハ（Ｐａｐｉｌｉｏ　ｘｕｔｈｕｓ）等、シロチョウ科のモンシロチョウ（Ｐｉｅｒｉｓ　ｒａｐａｅ）等、セセリチョウ科のイチモンジセセリ（Ｐａｒｎａｒａ　ｇｕｔｔａｔａ）等、シャクガ科のヨモギエダシャク（Ａｓｃｏｔｉｓ　ｓｅｌｅｎａｒｉａ）等、カレハガ科のマツカレハ（Ｄｅｎｄｒｏｌｉｍｕｓ　ｓｐｅｃｔａｂｉｌｉｓ）、オビカレハ（Ｍａｌａｃｏｓｏｍａ　ｎｅｕｓｔｒｉｕｍ　ｔｅｓｔａｃｅｕｍ）等、スズメガ科のエビガラスズメ（Ａｇｒｉｕｓ　ｃｏｎｖｏｌｖｕｌｉ）等、ドクガ科のチャドクガ（Ａｒｎａ　ｐｓｅｕｄｏｃｏｎｓｐｅｒｓａ）、ヒメシロモンドクガ（Ｏｒｙｇｉａ　ｒｅｃｅｎｓ　ａｐｐｒｏｘｉｍａｎｓ）、マイマイガ（Ｌｙｍａｎｔｒｉａ　ｄｉｓｐａｒ）等、ヒトリガ科のアメリカシロヒトリ（Ｈｙｐｈａｎｔｒｉａ　ｃｕｎｅａ）等、ヤガ科のタマナヤガ（Ａｇｒｏｔｉｓ　ｉｐｓｉｌｏｎ）、カブラヤガ（Ａｇｒｏｔｉｓ　ｓｅｇｅｔｕｍ）、タマナギンウワバ（Ａｕｔｏｇｒａｐｈａ　ｎｉｇｒｉｓｉｇｎａ）、オオタバコガ（Ｈｅｌｉｃｏｖｅｒｐａ　ａｒｍｉｇｅｒａ）、コーンイヤーワーム（Ｈｅｌｉｃｏｖｅｒｐａ　ｚｅａ）、タバコバドワーム（Ｈｅｌｉｏｔｈｉｓ　ｖｉｒｅｓｃｅｎｓ）、シロイチモジヨトウ（Ｓｐｏｄｏｐｔｅｒａ　ｅｘｉｇｕａ）、ハスモンヨトウ（Ｓｐｏｄｏｐｔｅｒａ　ｌｉｔｕｒａ）、ソイビーンルーパー（Ｃｈｒｙｓｏｄｅｉｘ　ｉｎｃｌｕｄｅｎｓ）、フォールアーミーワーム（Ｓｐｏｄｏｐｔｅｒａ　ｆｒｕｇｉｐｅｒｄａ）ブロンズドカットワーム（Ｎｅｐｈｅｌｏｄｅｓ　ｍｉｎｉａｎｓ）等を挙げることができる。 Examples of the Lepidoptera pests include, but are not limited to, Endoclita excrescens, bats of the family bat, Endospila 科 ampelopsia of the family of the family bats, etc .; Sea oysters (Archips @ fuscocupreanus), apple lizards (Adoxophys \ orana \ fasciata), Nashihimesingui (Grapholita @ molesta), chahamaki (Homona @ magnaigina, L. monella), European grape vine moss (Lobesia botrana), etc., Grape Hosohamaki (Eupoecilia ambiguella), etc. of the family Osohamaki; Iga (Tinea @ translucens), etc., Chibigaceae (Bucculatrix @ pyrivorella), etc., Coleoptera phyllophylla (Lyonetia @ clarkerella), and Gingham hamla (Coleoptera, Coleoptera, Coleoptera) (Vora); , Stag beetle (Nokona regalis), Scosinaceae (Synanthedin hector), etc., etc. Totroga @ cerealella, Pectinophora @ gossypiella, Tomato leaf miner (Tuta @ absoluta), etc .; , Ciliophidae (Ancylomia japonica), Chilo ｉsuppressalis, Chonopha mori (Cnaphalococlis medinalis), Awanomeiga (Ostrinia furnanomalis), Gyamomodara (L.) The moths (Conogethes @ punctiferlis), the cotton helicopter (Diaphania @ indica), the shibattoga (Parapediasia @ terrella), the European corn borer (Ostrinia @ nabilis), the sugar cane darga ga gaa da ga ga sara ata gaa da gaa ga (Diaphnia) (Galleria @ mellonella), etc., Tribidae grape triva (Nippoptilia @ vitis), etc., Swallowtail butterfly (Papilio @ xthus), etc., White butterfly (Pieris @ rapae), etc., etc. ra guttata), etc., etc. Geometridae family of Artemisia Eda Shakti (Ascotis selenaria), pine moth (Dendrolimus spectabilis of lasiocampidae), lackey moth (Malacosoma neustrium testaceum), etc., AGRIUS CONVOLVULI of sphingidae (Agrius convolvuli), etc., of Lymantriidae Arna Pseudoconspersa (Arna pseudoconspersa ), Orygia recens approximans, Lymantria dispar, and others, such as Hyphantria cunea, belonging to the family Noctuidae, and Agrotis ｇgigas, Agrotis ｇigas, from the family Noctuidae. tum), Tamanagin'uwaba (Autographa nigrisigna), cotton bollworm (Helicoverpa armigera), corn earworm (Helicoverpa zea), tobacco Bud worm (Heliothis virescens), beet armyworm (Spodoptera exigua), common cutworm (Spodoptera litura), soybean looper (Chrysodeix includens), Fall army worms (Spodoptera @ frugiperda) and bronzed cut worms (Nephelodes @ minians) can be exemplified.
　ハチ目害虫としては、例えば、ミフシハバチ科のチュウレンジハバチ（Ａｒｇｅ　ｐａｇａｎａ）等、ハバチ科のクリハバチ（Ａｐｅｔｈｙｍｕｓ　ｋｕｒｉ）、カブラハバチ（Ａｔｈａｌｉａ　ｒｏｓａｅ　ｒｕｆｉｃｏｒｎｉｓ）等、タマバチ科のクリタマバチ（Ｄｒｙｏｃｏｓｍｕｓ　ｋｕｒｉｐｈｉｌｕｓ）等、スズメバチ科のキイロスズメバチ（Ｖｅｓｐａ　ｓｉｍｉｌｌｉｍａ　ｘａｎｔｈｏｐｔｅｒａ）等、アリ科のヒアリ（Ｓｏｌｅｎｏｐｓｉｓ　ｉｎｖｉｃｔａ）、アルゼンチンアリ（Ｌｉｎｅｐｉｔｈｅｍａ　ｈｕｍｉｌｅ）等、ハキリバチ科のバラハキリバチ（Ｍｅｇａｃｈｉｌｅ　ｎｉｐｐｏｎｉｃａ）等を挙げることができる。 Examples of the honey bee pests include, for example, the wasp-family spp. (Agephygana), the wasp-family chestnut wasp (Apethymus kuri), the squamf wasp (Athalia rosae ruficornis), and the bee-family Drikyuurusi (C.) Ants (Solenopsis @ invicta), such as the Japanese hornet (Vespa @ simillima @ xanthoptera), and the ant family (Solenopsis @ invicta), and the Argentine ant (Lineipithema @ humile), etc., can be mentioned.
　トビムシ目害虫としては、例えば、マルトビムシ科のキボシマルトビムシ（Ｂｏｕｒｌｅｔｉｅｌｌａ　ｈｏｒｔｅｎｓｉｓ）等を挙げることができる。 Examples of the order Pests from the order of the order Tabanida include, for example, Bourletiella Hortensis of the family Martaviridae.
　シミ目害虫としては、例えば、シミ科のセイヨウシミ（Ｌｅｐｉｓｍａ　ｓａｃｃｈａｒｉｎａ）、ヤマトシミ（Ｃｔｅｎｏｌｅｐｉｓｍａ　ｖｉｌｌｏｓａ）等を挙げることができる。 As examples of the pests of Lepidoptera, there may be mentioned, for example, Lepidoptera saccharina (Lepidoptera) and Ctenolepisma (Vilosa).
　ゴキブリ目害虫としては、例えば、ゴキブリ科のワモンゴキブリ（Ｐｅｒｉｐｌａｎｅｔａ　ａｍｅｒｉｃａｎａ）、チャバネゴキブリ科のチャバネゴキブリ（Ｂｌａｔｔｅｌｌａ　ｇｅｒｍａｎｉｃａ）、シロアリ科のタイワンシロアリ（Ｏｄｏｎｔｏｔｅｒｍｅｓ　ｆｏｒｍｏｓａｎｕｓ）、レイビシロアリ科のアメリカカンザイシロアリ（Ｉｎｃｉｓｉｔｅｒｍｅｓ　ｍｉｎｏｒ）、ダイコクシロアリ（Ｃｒｙｐｔｏｔｅｒｍｅｓ ｄｏｍｅｓｔｉｃｕｓ）、ミゾガラシロアリ科のイエシロアリ（Ｃｏｐｔｏｔｅｒｍｅｓ　ｆｏｒｍｏｓａｎｕｓ）、ヤマトシロアリ（Ｒｅｔｉｃｕｌｉｔｅｒｍｅｓ ｓｐｅｒａｔｕｓ）等を挙げることができる。 As the cockroach pests, for example, cockroaches (Periplaneta @americana), German cockroaches (Blattella @germanica), termites of the termite family (Odontotermes @ Formicidae), and termites of the termites of the genus Asterica sect. (Cryptotermes @ domesticus), termites of the family Termite (Copterotermes @ formosanus), and termites (Reticulitermes @ speratus).
　チャタテムシ目害虫としては、例えば、コチャタテ科のコチャタテ（Ｔｒｏｇｉｕｍ　ｐｕｌｓａｔｏｒｉｕｍ）等、コナチャタテ科のウスグロチャタテ（Ｌｉｐｏｓｃｅｌｉｓ　ｃｏｒｒｏｄｅｎｓ）等を挙げることができる。 Examples of the insect pests of the order Psocoptera include, for example, Trochomium (Pulsatorium) of the family Papilionidae, and Usgrochatate (Liposcelis @ corrodens) of the family Papilionidae.
　ハサミムシ目害虫としては、例えば、オオハサミムシ科のオオハサミムシ（Ｌａｂｏｄｕｒａ　ｒｉｐａｒｉａ）等を挙げることができる。 と し て Examples of the earwig pests include, for example, Laberadidae (Labobodura riparia) belonging to the family Parasitidae.
　ハジラミ目害虫としては、例えば、トリハジラミ科のニワトリナガハジラミ等、ケモノハジラミ科のウシハジラミ（Ｄａｍａｌｉｎｉａ　ｂｏｖｉｓ）等を挙げることができる。 Examples of the insects of the order Lepidoptera include, for example, chicks of the family Apocynidae, such as the chicks of the family Apocynidae, and the lice of the family Psyllidae, Damalinia bovis.
　シラミ目害虫としては、例えば、ケモノジラミ科のブタジラミ（Ｈａｅｍａｔｏｐｉｎｕｓ　ｓｕｉｓ）等、ヒトジラミ科のヒトジラミ（Ｐｅｄｉｃｕｌｕｓ　ｈｕｍａｎｕｓ）等、ケモノホソジラミ科のイヌジラミ（Ｌｉｎｏｇｎａｔｈｕｓ　ｓｅｔｏｓｕｓ）等、ケジラミ科のケジラミ（Ｐｔｈｉｒｕｓ　ｐｕｂｉｓ）等を挙げることができる。 Examples of the lice pests include, for example, Haematopinus suis of the family Lamiidae, Pediculus humanus of the Laceae family, and the like and the genus Pis of the genus Pseudocephalus (Lingnathus ｔｏsetosus), such as the louse lice of the genus Lepidoptera, Licegrass. Can be.
　ダニ目害虫としては、例えば、ハシリダニ科のムギダニ（Ｐｅｎｔｈａｌｅｕｓ　ｍａｊｏｒ）等、ホコリダニ科のシクラメンホコリダニ（Ｐｈｙｔｏｎｅｍｕｓ　ｐａｌｌｉｄｕｓ）、チャノホコリダニ（Ｐｏｌｙｐｈａｇｏｔａｒｓｏｎｅｍｕｓ　ｌａｔｕｓ）等、シラミダニ科のシラミダニの一種（Ｓｉｔｅｒｏｐｔｅｓ　ｓｐ．）等、ヒメハダニ科のブドウヒメハダニ（Ｂｒｅｖｉｐａｌｐｕｓ　ｌｅｗｉｓｉ）等、ケナガハダニ科のナミケナガハダニ（Ｔｕｃｋｅｒｅｌｌａ　ｐａｖｏｎｉｆｏｒｍｉｓ）等、ハダニ科のアンズアケハダニ（Ｅｏｔｅｔｒａｎｙｃｈｕｓ　ｂｏｒｅｕｓ）、ミカンハダニ（Ｐａｎｏｎｙｃｈｕｓ　ｃｉｔｒｉ）、リンゴハダニ（Ｐａｎｏｎｙｃｈｕｓ　ｕｌｍｉ）、ナミハダニ（Ｔｅｔｒａｎｙｃｈｕｓ　ｕｒｔｉｃａｅ）、カンザワハダニ（Ｔｅｔｒａｎｙｃｈｕｓ　ｋａｎｚａｗａｉ）等、ナガクダフシダニ科のマツフシダニ（Ｔｒｉｓｅｔａｃｕｓ　ｐｉｎｉ）等、フシダニ科のミカンサビダニ（Ａｃｕｌｏｐｓ　ｐｅｌｅｋａｓｓｉ）、ナシサビダニ（Ｅｐｉｔｒｉｍｅｒｕｓ　ｐｙｒｉ）、シトラスラストマイト（Ｐｈｙｌｌｏｃｏｐｔｒｕｔａ　ｏｌｅｉｖｏｒａ）、トマトサビダニ（Ａｃｕｌｏｐｓ　ｌｙｃｏｐｅｒｓｉｃｉ）等、ハリナガフシダニ科のイヌツゲフシダニ（Ｄｉｐｔａｃｕｓ　ｃｒｅｎａｔａｅ）等、コナダニ科のムギコナダニ（Ａｌｅｕｒｏｇｌｙｐｈｕｓ　ｏｖａｔｕｓ）、ケナガコナダニ（Ｔｙｒｏｐｈａｇｕｓ　ｐｕｔｒｅｓｃｅｎｔｉａｅ）、ロビンネダニ（Ｒｈｉｚｏｇｌｙｐｈｕｓ　ｒｏｂｉｎｉ）、ヘギイタダニ科のミツバチヘギイタダニ（Ｖａｒｒｏａ　ｊａｃｏｂｓｏｎｉ）等、ワクモ科のワクモ（Ｄｅｒｍａｎｙｓｓｕｓ　ｇａｌｌｉｎａｅ）等、オオサシダニ科のトリサシダニ（Ｏｒｎｉｔｈｏｎｙｓｓｕｓ　ｓｙｌｖｉａｌｕｍ）等、マダニ科のオウシマダニ（Ｂｏｏｐｈｉｌｕｓ　ｍｉｃｒｏｐｌｕｓ）、クリイロコイタマダニ（Ｒｈｉｐｉｃｅｐｈａｌｕｓ　ｓａｎｇｕｉｎｅｕｓ）、フタトゲチマダニ（Ｈａｅｍａｐｈｙｓａｌｉｓ　ｌｏｎｇｉｃｏｒｎｉｓ）等、ヒゼンダニ科のヒゼンダニ（Ｓａｒｃｏｐｔｅｓ　ｓｃａｂｉｅｉ）等を挙げることができる。 Examples of the acarid pests include, for example, the house dust mite (Penthaleus major), the dust mite Cyclamen mite (Phytonemus pallidus), the typhoid mite (Polyphagotarsononemus latus), and the species of the family Dermatophagidae: And other spider mites (Eotetranychus mite) (Panionychus mite), such as the red mite (Brevipalpus lewisi), the spider mite (Tuckerella pavoniformis), and the spider mite (Eotetranychus mite). hus urticae), kanzawai (Tetranychus kanzawai), etc., Matsufushidani (Trisetacus pini of Nagakudafushidani family), etc., of Fushidani family tangerine rust mite (Aculops pelekassi), Nashisabidani (Epitrimerus pyri), citrus last mite (Phyllocoptruta oleivora), tomato rust mite (Aculops lycopersici ), Etc., such as Diptacus crenatae of the family Acaridae, Aleoglyphus ovatus of the family Acarina, Tyrophagus putrescentiae, and Robin nephrite (Rhiz oglyph). bini), Dermanicaceae (Varoa @ jacobsoni), etc. of the family Acaridae; Rhipicephalus @ sanguineus, Haematophysalis @ longicornis, etc., and Sarcoptes @ scabiei of the family Dermatophagoides.
　植物寄生性線虫類としては、例えば、ロンギドルス科のブドウオオハリセンチュウ（Ｘｉｐｈｉｎｅｍａ　ｉｎｄｅｘ）等、トリコドルス科のヒメユミハリセンチュウ（Ｐａｒａｔｒｉｃｈｏｄｏｒｕｓ　ｍｉｎｏｒ）等、ラブディティス科の一種（Ｒｈａｂｄｉｔｅｌｌａ　ｓｐ．）等、ティレンクス科の一種（Ａｇｌｅｎｃｈｕｓ　ｓｐ．）等、ティロドルス科の一種（Ｃｅｐｈａｌｅｎｃｈｕｓ　ｓｐ．）等、アングイナ科のイチゴメセンチュウ（Ｎｏｔｈｏｔｙｌｅｎｃｈｕｓ　ａｃｒｉｓ）、イモグサレセンチュウ（Ｄｉｔｙｌｅｎｃｈｕｓ　ｄｅｓｔｒｕｃｔｏｒ）等、ホプロライムス科のニセフクロセンチュウ（Ｒｏｔｙｌｅｎｃｈｕｌｕｓ　ｒｅｎｉｆｏｒｍｉｓ）、ナミラセンセンチュウ（Ｈｅｌｉｃｏｔｙｌｅｎｃｈｕｓ　ｄｉｈｙｓｔｅｒａ）等、パラティレンクス科のチャピンセンチュウ（Ｐａｒａｔｙｌｅｎｃｈｕｓ　ｃｕｒｖｉｔａｔｕｓ）等、メロイドギネ科のサツマイモネコブセンチュウ（Ｍｅｌｏｉｄｏｇｙｎｅ　ｉｎｃｏｇｎｉｔａ）、キタネコブセンチュウ（Ｍｅｌｏｉｄｏｇｙｎｅ　ｈａｐｌａ）、ジャワネコブセンチュウ（Ｍｅｌｏｉｄｏｇｙｎｅ　ｊａｖａｎｉｃａ）、コロンビアネコブセンチュウ（Ｍｅｌｏｉｄｏｇｙｎｅ　ｃｈｉｔｗｏｏｄｉ），ニセコロンビアネコブセンチュウ（Ｍｅｌｏｉｄｏｇｙｎｅ　ｆａｌｌａｘ）等、ヘテロデラ科のジャガイモシストセンチュウ（Ｇｌｏｂｏｄｅｒａ　ｒｏｓｔｏｃｈｉｅｎｓｉｓ）、ジャガイモシロシストセンチュウ（Ｇｌｏｂｏｄｅｒａ　ｐａｌｌｉｄａ）、ダイズシストセンチュウ（Ｈｅｔｅｒｏｄｅｒａ　ｇｌｙｃｉｎｅｓ）、テンサイシストセンチュウ（Ｈｅｔｅｒｏｄｅｒａ　Ｓｃｈａｃｈｔｉｉ）等、テロティレンクス科のナミイシュクセンチュウ（Ｔｙｌｅｎｃｈｏｒｈｙｎｃｈｕｓ　ｃｌａｙｔｏｎｉ）等、プシレンクス科のラシンセンチュウの一種（Ｐｓｉｌｅｎｃｈｕｓ　ｓｐ．）等、クリコネマ科のワセンチュウ類の一種（Ｃｒｉｃｏｎｅｍｏｉｄｅｓ　ｓｐ．）等、ティレンクルス科のミカンネセンチュウ（Ｔｙｌｅｎｃｈｕｌｕｓ　ｓｅｍｉｐｅｎｅｔｒａｎｓ）等、スフェロネマ科のツバキマルセンチュウ（Ｓｐｈａｅｒｏｎｅｍａ　ｃａｍｅｌｌｉａｅ）等、プラティレンクス科のカンキツネモグリセンチュウ（Ｒａｄｏｐｈｏｌｕｓ　ｃｉｔｒｏｐｈｉｌｕｓ）、バナナネモグリセンチュウ（Ｒａｄｏｐｈｏｌｕｓ　ｓｉｍｉｌｉｓ）、ニセネコブセンチュウ（Ｎａｃｏｂｂｕｓ　ａｂｅｒｒａｎｓ）、キタネグサレセンチュウ（Ｐｒａｔｙｌｅｎｃｈｕｓ　ｐｅｎｅｔｒａｎｓ）、ミナミネグサレセンチュウ（Ｐｒａｔｙｌｅｎｃｈｕｓ　ｃｏｆｆｅａｅ）、モロコシネグサレセンチュウ（Ｐｒａｔｙｌｅｎｃｈｕｓ　ｚｅａｅ）、パイナップルネグサレセンチュウ（Ｐｒａｔｙｌｅｎｃｈｕｓ　ｂｒａｃｈｙｕｒｕｓ）等、イオトンキウム科のヒラタケヒダコブセンチュウ（Ｉｏｔｏｎｃｈｉｕｍ　ｕｎｇｕｌａｔｕｍ）等、アフェレンクス科のニセネグサレセンチュウ（Ａｐｈｅｌｅｎｃｈｕｓ　ａｖｅｎａｅ）等、アフェレンコイデス科のイネシンガレセンチュウ（Ａｐｈｅｌｅｎｃｈｏｉｄｅｓ　ｂｅｓｓｅｙｉ）、イチゴセンチュウ（Ａｐｈｅｌｅｎｃｈｏｉｄｅｓ　ｆｒａｇａｒｉａｅ）等、パラシタフェレンクス科のマツノザイセンチュウ（Ｂｕｒｓａｐｈｅｌｅｎｃｈｕｓ　ｘｙｌｏｐｈｉｌｕｓ）等を挙げることができる。 The plant parasitic nematodes include, for example, a grape nematode (Xipinema index) of the family Longidols, a paratrichodor nematode (Paratrichodorus minor) of the family Trichodulaceae, a species of the family Rhabditela sp. Species of the family Tylodorus (Cephalenchus sp.), Etc., Strawberry nematodes of the Anguinaceae family (Notothilenchus acris), Imogaresenchu (Ditylenchus destructructor), and the like of the genus Rhynium sylterium, Rhynium resinus, and the family of the genus, Rhynium resinus Helicopterench s dihystera), etc., etc. tea pin nematodes of Paratirenkusu Department (Paratylenchus curvitatus), of Meroidogine Department of sweet potato root-knot nematode (Meloidogyne incognita), northern root-knot nematode (Meloidogyne hapla), Javanese root-knot nematode (Meloidogyne javanica), Columbia root-knot nematode (Meloidogyne chitwoodi), false Potato cyst nematodes (Globodera rostochiensis) of the family Heterodela, such as Colombian root knot nematodes (Meloidogyne fallax), potato cyst nematodes (Globodera pallida), soybean cysts Species of the family Psyllenchus (Psilenidae), such as the genus Psinus, Psylenchus (Hymenoptera), such as Heterodera @ glycines, Heterodesta @ Schachtii, and the like of the family Psyllenchus, such as Tylenchorhynchus @ claytoni. Cryconemoides @ sp.), Tylenculus semipenetrans, etc., Spheronema family, Camellia nematode (Sphaeronema camameliae), etc. Chu (Radopholus similis), false root-knot nematode (Nacobbus aberrans), Northern Negu Saleh nematode (Pratylenchus penetrans), South Negu Saleh nematode (Pratylenchus coffeae), sorghum Negu Saleh nematode (Pratylenchus zeae), pineapple Negu Saleh nematode (Pratylenchus brachyurus), etc., Iotonkiumu The family Aphilenchus nematodes (Iotonchium ngulatum) and the Apherenidae family Asenengusarevene and the apherenoides family Apelenchoides besseyi and the like. , Mention may be made of strawberry nematode (Aphelenchoides fragariae), etc., para Sita Ferre down box Department of pine wood nematode (Bursaphelenchus xylophilus) and the like.
　植物寄生性軟体動物としては、例えば、タニシモドキ科のスクミリンゴガイ（Ｐｏｍａｃｅａ　ｃａｎａｌｉｃｕｌａｔａ）等、アシヒダナメクジ科のアシヒダナメクジ（Ｌｅａｖｉｃａｕｌｉｓ　ａｌｔｅ）等、アフリカマイマイ科のアフリカマイマイ（Ａｃｈａｔｉｎａ　ｆｕｌｉｃａ）等、ナメクジ科のフタスジナメクジ（Ｍｅｇｈｉｍａｔｉｕｍ　ｂｉｌｉｎｅａｔｕｍ）等、オカモノアラガイ科のオカモノアラガイ（Ｓｕｃｃｉｎｅａｌａｕｔａ）等、パツラマイマイ科のパツラマイマイ（Ｄｉｓｃｕｓ　ｐａｕｐｅｒ）等、コハクガイ科のエゾコハクガイ（Ｚｏｎｉｔｏｉｄｅｓ　ｙｅｓｓｏｅｎｓｉｓ）等、コウラナメクジ科のコウラナメクジ（Ｌｉｍａｘ　ｆｌａｖｕｓ）、チャコウラナメクジ（Ｌｅｈｍａｎｎｉａ　ｖａｌｅｎｔｉａｎａ）、ノハラナメクジ（Ｄｅｒｏｃｅｒａｓ　ｒｅｔｉｃｕｌａｔｕｍ）等、ベッコウマイマイ科のハリマキビ（Ｐａｒａｋａｌｉｅｌｌａ　ｈａｒｉｍｅｎｓｉｓ）等、オナジマイマイ科のウスカワマイマイ（Ａｃｕｓｔａ　ｄｅｓｐｅｃｔａ　ｓｉｅｂｏｌｄｉａｎａ）、オナジマイマイ（Ｂｒａｄｙｂａｅｎａ　ｓｉｍｉｌａｒｉｓ）等を挙げることができる。 Examples of the plant-parasitic molluscs include, for example, Pomicea canaliculata and the like of the family Papilionidae, Levicaulis @alte of the family Aphididae, and Achatina @flicica of the family Achamidae and the like. Species of the family Agonaceae, such as Schimuxia sect. ), Leopardia slug (Lehmannia @ v) lentiana), Noharanamekuji (Deroceras reticulatum), etc., tortoiseshell snail family Harimakibi (Parakaliella harimensis), etc., the same snail family of mouse river snail (Acusta despecta sieboldiana), mention may be made of the same snail (Bradybaena similaris) and the like.
　その他の有害動物、不快動物、衛生害虫、家畜害虫、寄生虫等の有害生物としては、例えば、エビ目アメリカザリガニ科のアメリカザリガニ（Ｐｒｏｃａｍｂａｒｕｓ　ｃｌａｒｋｉｉ）等、ワラジムシ目のワラジムシ科のワラジムシ（Ｐｏｒｃｅｌｌｉｏ ｓｃａｂｅｒ）等、ダンゴムシ科のオカダンゴムシ（Ａｒｍａｄｉｌｌｉｄｉｕｍ　ｖｕｌｇａｒｅ）等、ゲジ目ゲジ科のゲジやオオムカデ目トビズムカデ（Ｓｃｏｌｏｐｅｎｄｒａ　ｓｕｂｓｐｉｎｉｐｅｓ）等のムカデ害虫目、オビヤスデ目ヤケヤスデ科のヤケヤスデ（Ｏｘｉｄｕｓ　ｇｒａｃｉｌｉｓ）等のヤスデ網害虫、クモ目ヒメグモ科のセアカゴケグモ（Ｔｈｅｒｉｄｉｉｄａｅ　ｈａｓｓｅｌｔｉｉ）等、クモ目フクログモ科のカバキコマチグモ（Ｃｈｉｒａｃａｎｔｈｉｕｍ　ｊａｐｏｎｉｃｕｍ）等、サソリ目のアフガンデスストーカー（Ａｎｄｒｏｃｔｏｎｕｓ　ｃｒａｓｓｉｃａｕｄａ）等、線形動物内部寄生虫である回虫類（Ａｓｃａｒｉｓ　ｌｕｍｂｒｉｃｏｉｄｅｓ）等、ぎょう虫類（Ｓｙｐｈａｃｉａ　ｓｐ．）等、フィラリア類（Ｗｕｃｈｅｒｅｒｉａ　ｂａｎｃｒｏｆｔｉ）等、扁形動物内部寄生虫である肝臓ジストマ（Ｄｉｓｔｏｍｕｍ　ｓｐ．）、肺臓ジストマ（Ｐａｒａｇｏｎｉｍｕｓ　ｗｅｓｔｅｒｍａｎｉｉ）、横川吸虫（Ｍｅｔａｇｏｎｉｍｕｓ　ｙｏｋｏｋａｗａｉ）、日本住血吸虫（Ｓｃｈｉｓｔｏｓｏｍａ　ｊａｐｏｎｉｃｕｍ）、有鉤条虫（Ｔａｅｎｉａ　ｓｏｌｉｕｍ）、無鉤条虫（Ｔａｅｎｉａｒｈｙｎｃｈｕｓ　ｓａｇｉｎａｔｕｓ）、エキノコックス（Ｅｃｈｉｎｏｃｏｃｃｕｓ　ｓｐ．）、広節裂頭条虫（Ｄｉｐｈｙｌｌｏｂｏｔｈｒｉｕｍ　ｌａｔｕｍ）等を挙げることができる。 Examples of other pests such as pests, unpleasant animals, sanitary pests, livestock pests, and parasites include, for example, a crayfish of the order Crayfish (Procambarus @ clarkii), a porphyria of the order Coleoptera, Porcellio @ scaber, and the like. Etc .; Armadillidium vulgare; Chiracan spiders of the order Araneidae, such as the redback spider (Therididae @ hasseltii) of the order Spiderae worms (Ascaris @ lumbricoides), etc. which are linear animal endoparasites, such as Afghanis stalkers (Androctonus @ crassicauda), etc .; Hepatic dystrophy (Distomum @ sp.), Which is a flatworm endoparasite, pulmonary dystrophy (Paragonimus @ westermanii), flukes Yokokawa (Metagonimus @ yokokawai), Schistosoma @ japonicum, H. Insects (Taeniarhynchus @ saginatus), Echinococcus (E chinococcus @ sp.), Diphyllobothrium @ latum, and the like.
　本発明の有害生物防除剤は、既存の有害生物防除剤に抵抗性を獲得した、前記に例示した有害生物等にも防除効果を示す。又、本発明の有害生物防除剤は、遺伝子組換え、人工交配等で害虫耐性、病害耐性、除草剤耐性等の特性を獲得した植物に使用することもできる。 有害 The pest control agent of the present invention has a control effect on the pests and the like exemplified above, which have acquired resistance to the existing pest control agent. The pesticidal composition of the present invention can also be used for plants that have acquired characteristics such as insect resistance, disease resistance, and herbicide resistance by genetic recombination, artificial crossing, and the like.
　本発明の「育種法又は遺伝子組換え技術により耐性を付与された植物」とは、古典的な品種交配による耐性付与、遺伝子組み換え技術による耐性付与だけでなく、これまでの交配技術に分子生物学的な手法を組み合わせた新育種技術（Ｎｅｗ　Ｐｌａｎｔ　Ｂｒｅｅｄｉｎｇ　Ｔｅｃｈｎｉｑｕｅｓ，　ＮＢＴs）により耐性付与された植物も含む。新育種技術（ＮＢＴｓ）は書籍「新しい植物育種技術を理解しよう」（国際文献社、大澤良、江面浩　著）、レビュー記事「Ｇｅｎｏｍｅ　Ｅｄｉｔｉｎｇ　Ｔｏｏｌｓ　ｉｎ　Ｐｌａｎｔｓ」（Ｇｅｎｅｓ　２０１７,８, ３９９、Ｔａｐａｎ　Ｋｕｍａｒ　Ｍｏｈａｎｔａ、Ｔｕｆａｉｌ　Ｂａｓｈｉｒ、Ａｂｅｅｒ　Ｈａｓｈｅｍ、Ｅｌｓａｙｅｄ　Ｆａｔｈｉ　Ａｂｄ＿Ａｌｌａｈ　ａｎｄ　Ｈａｎｈｏｎｇ　Ｂａｅ　著）等に記載されている。 The term "plant to which resistance has been imparted by a breeding method or a genetic recombination technique" of the present invention means not only resistance imparting by classical breeding and genetic conferring techniques, but also molecular biology Also include plants to which resistance has been imparted by a new breeding technique (New Plant Breeding Technologies, NBTs) that combines conventional techniques. New breeding techniques (NBTs) are described in the book "Let's Understand New Plant Breeding Techniques" (International Literature Company, Ryo Osawa, Hiroshi Emen), review article "Genome Editing Tools" in Plants (Genes 2017, 8, 399, Tapan Kumar Moanta). Tufail, Bashir, Abeer, Hashem, Elsayed, Fathi, Abd_Allah, and Hanghong, Bae).
　次に、本発明化合物の製造方法、製剤方法並びに用途を下記の実施例で詳細に説明するが、本発明はこれら実施例に何ら制約されるものではない。尚、本発明化合物の物性値である融点は、ヤナコ製ＭＰ－５００Ｖ微量融点測定装置にて測定した。屈折率は、アタゴ製アッベ屈折計を用いて測定した。１Ｈ　ＮＭＲスペクトラムは、日本電子製ＪＮＭ－ＬＡ４００（４００　ＭＨｚ）、ＪＮＭ－ＬＡ３００（３００　ＭＨｚ）又はＪＮＭ－ＥＣＳ３００（３００　ＭＨｚ）を用いて、テトラメチルシラン（ＴＭＳ）を内部標準とし測定した。 Next, the production method, formulation method and use of the compound of the present invention will be described in detail in the following examples, but the present invention is not limited to these examples. The melting point, which is the physical property value of the compound of the present invention, was measured with a Yanaco MP-500V trace melting point measuring apparatus. The refractive index was measured using an Atago Abbe refractometer. The 1 H NMR spectrum was measured using JNM-LA400 (400 MHz), JNM-LA300 (300 MHz) or JNM-ECS300 (300 MHz) manufactured by JEOL with tetramethylsilane (TMS) as an internal standard.
　又、本発明化合物の製造中間体の製造法も併せて記載する。 Also described is a method for producing an intermediate for producing the compound of the present invention.
［実施例１］
　５－［５－アミノ－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド（本発明の化合物番号：Ａ－０００１）の製造 [Example 1]
5- [5-amino-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl-N- (2,2,2-trifluoroethyl ) Preparation of benzoic acid amide (Compound No. A-0001 of the present invention)
　（１）５－アミノ－４－フルオロ－２－メチル安息香酸エチルの製造
　国際公開特許公報ＷＯ２００９／０７８４８１号記載の方法に準じて製造した４－フルオロ－２－メチル－５－ニトロ安息香酸エチル１６．８０ｇ（７３．９５ｍｍｏｌ）をエタノール８００ｍＬに溶かし、１０％パラジウムカーボン１．６８ｇを加えた。その後、水素雰囲気下、室温で５時間撹拌した。反応終了後、反応混合物をセライト濾過し、濾液を減圧下濃縮した。残渣をシリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝３：１）にて精製し、目的物を１２．２０ｇ（収率８４％）得た。 (1) Production of ethyl 5-amino-4-fluoro-2-methylbenzoate 0.80 g (73.95 mmol) was dissolved in 800 mL of ethanol, and 1.68 g of 10% palladium carbon was added. Thereafter, the mixture was stirred at room temperature for 5 hours under a hydrogen atmosphere. After completion of the reaction, the reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, n-hexane: ethyl acetate = 3: 1) to obtain 12.20 g (yield 84%) of the desired product.
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 1.37(3H, t), 2.48(3H, s), 3.66(2H, brs), 4.32(2H, q), 6.85(1H, d), 7.41(1H, d) 1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 1.37 (3H, t), 2.48 (3H, s), 3.66 (2H, brs), 4.32 (2H, q), 6.85 (1H, d), 7.41 (1H, d)
　（２）４－フルオロ－５－ヒドラジニル－２－メチル安息香酸エチルの製造
　５－アミノ－４－フルオロ－２－メチル安息香酸エチル２４．４５ｇ（１２４．０ｍｍｏｌ）を濃塩酸１００ｍＬに懸濁し、氷冷下、０～５℃にて亜硝酸ナトリウム９．４１ｇ（１３６ｍｍｏｌ）を３０ｍＬの水に溶解させた水溶液を滴下した。更に滴下終了後、同温度に保ちながら１時間撹拌した。塩化スズ４７．０２ｇ（２４７．９ｍｍｏｌ）を濃塩酸１００ｍＬに溶解した溶液を、同温度に保ちながら前述の反応混合物に徐々に滴下し、さらに室温で２時間撹拌した。反応終了後、酢酸エチルを加え、水酸化ナトリウム水溶液で中和し、不溶物をセライト濾過した。有機層を水洗し、無水硫酸マグネシウムで乾燥した。溶媒を減圧下留去して、得られた粗生成物をｎ－ヘキサンで洗浄し、目的物を２０．４８ｇ（収率７８％）得た。 (2) Production of ethyl 4-fluoro-5-hydrazinyl-2-methylbenzoate 24.45 g (124.0 mmol) of ethyl 5-amino-4-fluoro-2-methylbenzoate was suspended in 100 mL of concentrated hydrochloric acid, and the suspension was added to ice. Under cooling, an aqueous solution in which 9.41 g (136 mmol) of sodium nitrite was dissolved in 30 mL of water was added dropwise at 0 to 5 ° C. After the addition, the mixture was stirred for 1 hour while maintaining the same temperature. A solution of 47.02 g (247.9 mmol) of tin chloride dissolved in 100 mL of concentrated hydrochloric acid was gradually added dropwise to the above reaction mixture while maintaining the same temperature, and the mixture was further stirred at room temperature for 2 hours. After completion of the reaction, ethyl acetate was added, the mixture was neutralized with an aqueous sodium hydroxide solution, and insolubles were filtered through celite. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained crude product was washed with n-hexane to obtain 20.48 g (yield 78%) of the desired product.
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 1.39(3H, t), 2.50(3H, s), 3.59(2H, brs), 4.35(2H, q), 5.34(1H, brs), 6.85(1H, d), 7.66(1H, d) 1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 1.39 (3H, t), 2.50 (3H, s), 3.59 (2H, brs), 4.35 (2H, q), 5.34 (1H, brs), 6.85 (1H, d), 7.66 (1H, d)
　（３）４－フルオロ－２－メチル－５－［２－（２，２，２－トリフルオロエチリデン）ヒドラジニル］安息香酸エチルの製造
　４－フルオロ－５－ヒドラジニル－２－メチル安息香酸エチル１０．００ｇ（４７．１２ｍｍｏｌ）、トリフルオロアセトアルデヒドエチルヘミアセタール１０．１８ｇ（７０．６５ｍｍｏｌ）、ｐ－トルエンスルホン酸一水和物０．４１ｇ（２．２ｍｍｏｌ）、エタノール７０ｍＬの混合物を４．５時間加熱還流した。室温にて放冷後、得られた反応混合物を減圧下濃縮し、粗製の目的物を得た。精製することなく、このまま次の工程に用いた。 (3) Production of ethyl 4-fluoro-2-methyl-5- [2- (2,2,2-trifluoroethylidene) hydrazinyl] benzoate Ethyl 4-fluoro-5-hydrazinyl-2-methylbenzoate A mixture of 00 g (47.12 mmol), 10.18 g (70.65 mmol) of trifluoroacetaldehyde ethyl hemiacetal, 0.41 g (2.2 mmol) of p-toluenesulfonic acid monohydrate, and 70 mL of ethanol was heated for 4.5 hours. Refluxed. After cooling at room temperature, the obtained reaction mixture was concentrated under reduced pressure to obtain a crude target product. This was used for the next step without purification.
　（４）５－［２－（１－ブロモ－２，２，２－トリフルオロエチリデン）ヒドラジニル］－４－フルオロ－２－メチル安息香酸エチルの製造
　粗製の４－フルオロ－２－メチル－５－［２－（２，２，２－トリフルオロエチリデン）ヒドラジニル］安息香酸エチルをＮ，Ｎ－ジメチルホルムアミド３５ｍＬに溶解し、氷冷下、０～５℃にて、Ｎ－ブロモコハク酸イミド８．５５ｇ（４８．０ｍｍｏｌ）を加え、同温度に保ちながら１時間撹持した。反応終了後、水を加え、酢酸エチルにて抽出し、得られた有機層を飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、粗製の目的物を得た。精製することなく、このまま次の工程に用いた。 (4) Production of ethyl 5- [2- (1-bromo-2,2,2-trifluoroethylidene) hydrazinyl] -4-fluoro-2-methylbenzoate Crude 4-fluoro-2-methyl-5 Ethyl [2- (2,2,2-trifluoroethylidene) hydrazinyl] benzoate is dissolved in 35 mL of N, N-dimethylformamide and 8.55 g of N-bromosuccinimide at 0-5 ° C. under ice-cooling. (48.0 mmol) was added, and the mixture was stirred for 1 hour while maintaining the same temperature. After completion of the reaction, water was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude target product. This was used for the next step without purification.
　（５）５－［５－アミノ－３－（トリフルオロメチル）－１Ｈ－１，２，４－ト
リアゾール－１－イル］－４－フルオロ－２－メチル安息香酸エチル（本発明の化合物番号：Ｃ－０００２）の製造
　粗製の５－［２－（１－ブロモ－２，２，２－トリフルオロエチリデン）ヒドラジニル］－４－フルオロ－２－メチル安息香酸エチル、Ｓ－メチルイソチオ尿素ヨウ化水素塩１５．４１ｇ（７０．６７ｍｍｏｌ）、テトラヒドロフラン１４０ｍＬの混合物に、室温下、トリエチルアミン１４．３０ｇ（１４１．３ｍｍｏｌ）を加え、さらに、３時間加熱還流した。室温にて放冷後、反応混合物を減圧下濃縮し、残渣に水を加え酢酸エチルにて抽出し、得られた有機層を飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、得られた粗生成物をｎ－ヘキサンとジイソプロピルエーテルで洗浄し、目的物を１１．６３ｇ（収率７４％、３工程）得た。 (5) Ethyl 5- [5-amino-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoate (Compound No. of the present invention: C-0002) Production of crude ethyl 5- [2- (1-bromo-2,2,2-trifluoroethylidene) hydrazinyl] -4-fluoro-2-methylbenzoate, S-methylisothiourea hydroiodide To a mixture of 15.41 g (70.67 mmol) and 140 mL of tetrahydrofuran, 14.30 g (141.3 mmol) of triethylamine was added at room temperature, and the mixture was further heated under reflux for 3 hours. After cooling at room temperature, the reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained crude product was washed with n-hexane and diisopropyl ether to obtain 11.63 g (yield 74%, 3 steps) of the desired product.
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 1.40(3H, t), 2.70(3H, s), 4.37(2H, q), 5.20(2H, brs), 7.21(1H, d), 8.13(1H, d) 1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 1.40 (3H, t), 2.70 (3H, s), 4.37 (2H, q), 5.20 (2H, brs), 7.21 (1H, d), 8.13 (1H, d)
　（６）５－［５－アミノ－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸（本発明の化合物番号：Ｂ－０００１）の製造
　５－［５－アミノ－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸エチル７．１４ｇ（２１．５ｍｍｏｌ）、メタノール４０ｍＬ、テトラヒドロフラン８０ｍＬ、水４０ｍＬの混合物に、水酸化リチウム一水和物２．７１ｇ（６４．６ｍｍｏｌ）を加え、室温で１．５時間撹拌した。反応終了後、得られた反応混合物を減圧下濃縮し、残渣に１０％クエン酸水溶液を加えて反応混合物を酸性にし、固体を析出させた。固体をろ過、水洗、乾燥させ、粗製の目的物を６．０９ｇ（収率９３％）得た。 (6) 5- [5-amino-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoic acid (Compound No. B of the present invention) -0001) 7.14 g of ethyl 5- [5-amino-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoate (21 2.5 mmol), 40 mL of methanol, 80 mL of tetrahydrofuran, and 40 mL of water, 2.71 g (64.6 mmol) of lithium hydroxide monohydrate was added, and the mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, the obtained reaction mixture was concentrated under reduced pressure, and a 10% aqueous citric acid solution was added to the residue to acidify the reaction mixture, thereby depositing a solid. The solid was filtered, washed with water, and dried to obtain 6.09 g of a crude target product (yield: 93%).
　1H-NMRデータ(400MHz,DMSO-d6/TMS δ(ppm)): 2.62(3H, s), 7.04(2H, s), 7.51(1H, d), 7.98(1H, d), 13.21(1H, brs) 1 H-NMR data (400 MHz, DMSO-d 6 / TMS δ (ppm)): 2.62 (3H, s), 7.04 (2H, s), 7.51 (1H, d), 7.98 (1H, d), 13.21 ( 1H, brs)
　（７）５－［５－アミノ－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミドの製造
　５－［５－アミノ－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸３．６２ｇ（１１．９ｍｍｏｌ）、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩２．７４ｇ（１４．３ｍｍｏｌ）、１－ヒドロキシベンゾトリアゾール一水和物２．１９ｇ（１４．３ｍｍｏｌ）、ジクロロメタン８０ｍＬ、テトラヒドロフラン８０ｍＬの混合物に、氷冷下、２，２，２－トリフルオロエチルアミン２．３６ｇ（２３．８ｍｍｏｌ）、トリエチルアミン２．４１ｇ（２３．８ｍｍｏｌ）を加え、室温で２４時間撹拌した。反応終了後、得られた反応混合物を減圧下濃縮し、残渣に酢酸エチルを加え、有機層を飽和炭酸水素ナトリウム水溶液、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝１：２）にて精製し、目的物を４．０５ｇ（収率８８％）得た。 (7) 5- [5-amino-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl-N- (2,2,2- 2. Preparation of (trifluoroethyl) benzoic acid amide 5- [5-amino-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoic acid 62 g (11.9 mmol), 2.74 g (14.3 mmol) of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 2.19 g (14.3 mmol) of 1-hydroxybenzotriazole monohydrate, 2.36 g (23.8 mmol) of 2,2,2-trifluoroethylamine and 2.41 of triethylamine were added to a mixture of 80 mL of dichloromethane and 80 mL of tetrahydrofuran under ice cooling. g (23.8 mmol) was added, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the obtained reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 2) to obtain 4.05 g of the desired product (88% yield).
　1H-NMRデータ(400MHz,DMSO-d6/TMS δ(ppm)): 2.43(3H, s), 4.03-4.09(2H, m), 7.04(2H, s), 7.48(1H, d), 7.60(1H, d), 9.06(1H, t)  1 H-NMR data (400 MHz, DMSO-d 6 / TMS δ (ppm)): 2.43 (3H, s), 4.03-4.09 (2H, m), 7.04 (2H, s), 7.48 (1H, d), 7.60 (1H, d), 9.06 (1H, t)
［実施例２］
　５－［５－アセトアミド－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド（本発明の化合物番号：Ａ－００７７）の製造 [Example 2]
5- [5-acetamido-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl-N- (2,2,2-trifluoroethyl ) Preparation of benzoic acid amide (Compound No. A-0077 of the present invention)
　（１）５－［５－（Ｎ－アセチルアセトアミド）－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸エチル（本発明の化合物番号：Ｃ－００８３）の製造
　５－［５－アミノ－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸エチル０．８４ｇ（２．５ｍｍｏｌ）のトルエン溶液２０ｍＬに塩化アセチル１．９８ｇ（２５．２ｍｍｏｌ）を加え、４時間加熱還流した後、さらに塩化アセチル２０ｍＬを加え、２０時間加熱還流した。室温にて放冷後、得られた反応混合物を減圧下濃縮し、残渣をシリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝２：１）にて精製し、目的物を１．０２ｇ（収率９７％）得た。 (1) Ethyl 5- [5- (N-acetylacetamido) -3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoate Preparation of Compound No. C-0083 of the Invention 5- [5-Amino-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoic acid 1.98 g (25.2 mmol) of acetyl chloride was added to 20 mL of a toluene solution of 0.84 g (2.5 mmol) of ethyl, and the mixture was heated under reflux for 4 hours. Then, 20 mL of acetyl chloride was further added, and the mixture was heated under reflux for 20 hours. After cooling at room temperature, the obtained reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 1.02 g of the desired product. (97% yield).
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 1.40(3H, t), 2.34(6H, s), 2.70(3H, s), 4.36(2H, q), 7.17(1H, d), 8.09(1H, d) 1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 1.40 (3H, t), 2.34 (6H, s), 2.70 (3H, s), 4.36 (2H, q), 7.17 (1H, d), 8.09 (1H, d)
　（２）５－［５－アセトアミド－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸エチル（本発明の化合物番号：Ｃ－００８２）の製造
　５－［５－（Ｎ－アセチルアセトアミド）－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸エチル１．０２ｇ（２．４５ｍｍｏｌ）、エタノール５ｍＬ、水５ｍＬの混合物に、炭酸水素ナトリウム０．６２ｇ（７．４ｍｍｏｌ）を加え、室温で３時間撹拌した後、さらに炭酸カリウム０．１０ｇ（０．７２ｍｍｏｌ）を加え、室温で３時間撹拌した。反応終了後、酢酸エチルを加え、有機層を水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝１：1）にて精製し、目的物を０．７８ｇ（収率８５％）得た。 (2) Ethyl 5- [5-acetamido-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoate (Compound No. of the present invention: Preparation of C-0082) 5- [5- (N-acetylacetamido) -3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoic acid 0.62 g (7.4 mmol) of sodium hydrogen carbonate was added to a mixture of 1.02 g (2.45 mmol) of ethyl, 5 mL of ethanol, and 5 mL of water, and the mixture was stirred at room temperature for 3 hours. 72 mmol) and stirred at room temperature for 3 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 1) to obtain 0.78 g (yield: 85%) of the desired product.
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 1.39(3H, t), 2.22(3H, brs), 2.70(3H, s), 4.37(2H, q), 7.16(1H, d), 8.15(1H, d) 1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 1.39 (3H, t), 2.22 (3H, brs), 2.70 (3H, s), 4.37 (2H, q), 7.16 (1H, d), 8.15 (1H, d)
　（３）５－［５－アセトアミド－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸（本発明の化合物番号：Ｂ－００７７）の製造
　５－［５－アセトアミド－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸エチル０．６８ｇ（１．８ｍｍｏｌ）、メタノール１０ｍＬ、テトラヒドロフラン５ｍＬ、水１０ｍＬの混合物に、水酸化リチウム一水和物０．３８ｇ（９．１ｍｍｏｌ）を加え、室温で一時間撹拌した。反応終了後、酢酸エチルを加え、有機層を２Ｎ塩酸、水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、粗製の目的物を０．５２ｇ（収率８３％）得た。 (3) 5- [5-acetamido-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoic acid (Compound No. B of the present invention) -0077) Preparation of Ethyl 5- [5-acetamido-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoate 0.68 g (1 .8 mmol), 10 mL of methanol, 5 mL of tetrahydrofuran, and 10 mL of water were added 0.38 g (9.1 mmol) of lithium hydroxide monohydrate, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with 2N hydrochloric acid, water, and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.52 g (yield: 83%) of a crude target product.
　1H-NMRデータ(400MHz,DMSO-d6/TMS δ(ppm)): 1.98(3H, s), 2.62(3H, s), 7.52(1H, d), 8.06(1H, d), 11.20(1H, brs), 13.23(1H, brs) 1 H-NMR data (400 MHz, DMSO-d 6 / TMS δ (ppm)): 1.98 (3H, s), 2.62 (3H, s), 7.52 (1H, d), 8.06 (1H, d), 11.20 ( 1H, brs), 13.23 (1H, brs)
　（４）５－［５－アセトアミド－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミドの製造
　５－［５－アセトアミド－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸０．４０ｇ（１．２ｍｍｏｌ）、２，２，２－トリフルオロエチルアミン０．１４ｇ（１．４ｍｍｏｌ）、１－ヒドロキシベンゾトリアゾール一水和物０．１６ｇ（１．０ｍｍｏｌ）、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩０．２７ｇ（１．４ｍｍｏｌ）、ジクロロメタン１０ｍＬの混合物に、氷冷下、トリエチルアミン０．２８ｇ（２．８ｍｍｏｌ）を加え、室温で一晩撹拌した。反応終了後、酢酸エチルを加え、有機層を水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝１：２）にて精製し、目的物を０．３５ｇ（収率７１％）得た。 (4) 5- [5-acetamido-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl-N- (2,2,2- Preparation of (trifluoroethyl) benzoic acid amide 5- [5-acetamido-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoic acid 40 g (1.2 mmol), 2,4,2-trifluoroethylamine 0.14 g (1.4 mmol), 1-hydroxybenzotriazole monohydrate 0.16 g (1.0 mmol), 1-ethyl-3- ( 0.28 g (2.8 mmol) of triethylamine was added to a mixture of 0.27 g (1.4 mmol) of 3-dimethylaminopropyl) carbodiimide hydrochloride and 10 mL of dichloromethane under ice-cooling. And stirred overnight at room temperature. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 2) to obtain 0.35 g of the desired product (yield: 71%).
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 2.20(3H, brs), 2.53(3H, s), 4.04-4.15(2H, m), 6.65(1H, t), 7.15(1H, d), 7.62(1H, d), 8.89(1H, brs) 1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 2.20 (3H, brs), 2.53 (3H, s), 4.04-4.15 (2H, m), 6.65 (1H, t), 7.15 ( 1H, d), 7.62 (1H, d), 8.89 (1H, brs)
［実施例３］
　５－［５－アミノ－３－（ジフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド（本発明の化合物番号：Ａ－０２４３）の製造 [Example 3]
5- [5-amino-3- (difluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl-N- (2,2,2-trifluoroethyl) Production of benzoic acid amide (Compound No. of the present invention: A-0243)
　（１）５－［２－（２，２－ジフルオロアセチル）ヒドラジニル］－４－フルオロ－２－メチル安息香酸エチルの製造
　４－フルオロ－５－ヒドラジニル－２－メチル安息香酸エチル３．３７ｇ（１５．９ｍｍｏｌ）、ジフルオロ酢酸エチル１１．８ｇ（９５．１ｍｍｏｌ）， テトラヒドロフラン３０ｍＬの混合物を５０℃で７．５時間撹拌した後、さらに１．５時間加熱還流した。
室温にて放冷後、得られた反応混合物を減圧下濃縮し、残渣をシリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝３：１）にて精製し、目的物を２．５０ｇ（収率５４％）得た。 (1) Production of ethyl 5- [2- (2,2-difluoroacetyl) hydrazinyl] -4-fluoro-2-methylbenzoate 3.37 g of ethyl 4-fluoro-5-hydrazinyl-2-methylbenzoate (15 1.9 mmol), 11.8 g (95.1 mmol) of ethyl difluoroacetate, and 30 mL of tetrahydrofuran were stirred at 50 ° C. for 7.5 hours, and then heated and refluxed for 1.5 hours.
After cooling at room temperature, the obtained reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3: 1) to obtain 2.50 g of the desired product (54% yield).
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 1.38(3H, t), 2.52(3H, s), 4.33(2H, q), 6.06(1H, t), 6.19(1H, s), 6.94(1H, d), 7.51(1H, d) , 8.08(1H, brs) 1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 1.38 (3H, t), 2.52 (3H, s), 4.33 (2H, q), 6.06 (1H, t), 6.19 (1H, s), 6.94 (1H, d), 7.51 (1H, d), 8.08 (1H, brs)
　（２）５－［２－（１－クロロ－２，２－ジフルオロエチリデン）ヒドラジニル］－４－フルオロ－２－メチル安息香酸エチルの製造
　５－［２－（２，２－ジフルオロアセチル）ヒドラジニル］－４－フルオロ－２－メチル安息香酸エチル２．５０ｇ（８．６１ｍｍｏｌ）、四塩化炭素３．９７ｇ（２５．８ｍｍｏｌ）、トリフェニルホスフィン２．９４ｇ（１１．２ｍｍｏｌ）、アセトニトリル３０ｍＬの混合物を２時間加熱還流した。室温にて放冷後、得られた反応混合物を減圧下濃縮し、残渣をシリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝４：１）にて精製し、目的物を２．３８ｇ（収率９０％）得た。 (2) Production of ethyl 5- [2- (1-chloro-2,2-difluoroethylidene) hydrazinyl] -4-fluoro-2-methylbenzoate 5- [2- (2,2-difluoroacetyl) hydrazinyl] A mixture of 2.50 g (8.61 mmol) of ethyl-4-fluoro-2-methylbenzoate, 3.97 g (25.8 mmol) of carbon tetrachloride, 2.94 g (11.2 mmol) of triphenylphosphine and 30 mL of acetonitrile was added to a mixture of 2 parts. Heated to reflux for an hour. After cooling at room temperature, the obtained reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1) to obtain 2.38 g of the desired product. (90% yield).
　（３）５－［５－アミノ－３－（ジフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸エチル（本発明の化合物番号：Ｃ－０２５１）の製造
　５－［２－（１－クロロ－２，２－ジフルオロエチリデン）ヒドラジニル］－４－フルオロ－２－メチル安息香酸エチル２．３８ｇ（７．７１ｍｍｏｌ）、Ｓ－メチルイソチオ尿素ヨウ化水素塩２．５２ｇ（１１．６ｍｍｏｌ）、テトラヒドロフラン３０ｍＬの混合物に、室温下、トリエチルアミン２．３４ｇ（２３．１ｍｍｏｌ）を加え、さらに、７．５時間加熱還流した。室温にて放冷後、得られた反応混合物を減圧下濃縮し、残渣に水を加え酢酸エチルにて抽出し、得られた有機層を飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝１：１～２：３）にて精製し、目的物を０．７６ｇ（収率３１％）得た。 (3) Ethyl 5- [5-amino-3- (difluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoate (Compound No .: C of the present invention) 2.38 g (7.71 mmol) of ethyl 5- [2- (1-chloro-2,2-difluoroethylidene) hydrazinyl] -4-fluoro-2-methylbenzoate, iodide of S-methylisothiourea To a mixture of 2.52 g (11.6 mmol) of the hydrogen salt and 30 mL of tetrahydrofuran, 2.34 g (23.1 mmol) of triethylamine was added at room temperature, and the mixture was further heated under reflux for 7.5 hours. After cooling at room temperature, the obtained reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate.The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. did. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 1 to 2: 3) to obtain 0.76 g of the desired product (yield 31%). Was.
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 1.40(3H, t), 2.69(3H, s), 4.37(2H, q), 4.66(2H, brs), 6.60(1H, t), 7.19(1H, d), 8.12(1H, d) 1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 1.40 (3H, t), 2.69 (3H, s), 4.37 (2H, q), 4.66 (2H, brs), 6.60 (1H, t), 7.19 (1H, d), 8.12 (1H, d)
　（４）５－［５－アミノ－３－（ジフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸（本発明の化合物番号：Ｂ－０２４０）の製造
　５－［５－アミノ－３－（ジフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸エチル０．７６ｇ（２．４ｍｍｏｌ）、メタノール５ｍＬ、テトラヒドロフラン１０ｍＬ、水５ｍＬの混合物に、水酸化リチウム一水和物０．３０ｇ（７．２ｍｍｏｌ）を加え、０℃で１．５時間撹拌した後、さらに室温で１時間撹拌した。反応終了後、得られた反応混合物を減圧下濃縮し、残渣に１０％クエン酸水溶液を加えて反応混合物を酸性にし、固体を析出させた。固体をろ過、水洗、乾燥させ、粗製の目的物を０．６３ｇ（収率９１％）得た。 (4) 5- [5-amino-3- (difluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoic acid (Compound No .: B- Production of ethyl 5- [5-amino-3- (difluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoate 0.76 g (2.4 mmol) ), 5 mL of methanol, 10 mL of tetrahydrofuran, and 5 mL of water, added 0.30 g (7.2 mmol) of lithium hydroxide monohydrate, stirred at 0 ° C for 1.5 hours, and further stirred at room temperature for 1 hour. . After completion of the reaction, the obtained reaction mixture was concentrated under reduced pressure, and a 10% aqueous citric acid solution was added to the residue to acidify the reaction mixture, thereby depositing a solid. The solid was filtered, washed with water, and dried to obtain 0.63 g (yield 91%) of a crude target product.
　1H-NMRデータ(400MHz,DMSO-d6/TMS δ(ppm)): 2.61(3H, s), 6.81(2H, s), 6.85(1H, t), 7.49(1H, d), 7.93(1H, d), 13.22(1H, brs) 1 H-NMR data (400 MHz, DMSO-d 6 / TMS δ (ppm)): 2.61 (3H, s), 6.81 (2H, s), 6.85 (1H, t), 7.49 (1H, d), 7.93 ( 1H, d), 13.22 (1H, brs)
　（５）５－［５－アミノ－３－（ジフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミドの製造
　５－［５－アミノ－３－（ジフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸０．６３ｇ（２．２ｍｍｏｌ）、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩０．５１ｇ（２．７ｍｍｏｌ）、１－ヒドロキシベンゾトリアゾール一水和物０．４０ｇ（２．６ｍｍｏｌ）、ジクロロメタン２０ｍＬ、テトラヒドロフラン２０ｍＬの混合物に、氷冷下、２，２，２－トリフルオロエチルアミン０．４４ｇ（４．４ｍｍｏｌ）、トリエチルアミン０．４５ｇ（４．５ｍｍｏｌ）を加え、室温で２４時間撹拌した。反応終了後、得られた反応混合物を減圧下濃縮し、残渣に酢酸エチルを加え、有機層を飽和炭酸水素ナトリウム水溶液、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝１：２）にて精製し、目的物を０．５２ｇ（収率６４％）得た。 (5) 5- [5-amino-3- (difluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl-N- (2,2,2-tri Preparation of fluoroethyl) benzoic acid amide 0.63 g of 5- [5-amino-3- (difluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoic acid ( 2.2 mmol), 0.51 g (2.7 mmol) of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 0.40 g (2.6 mmol) of 1-hydroxybenzotriazole monohydrate, 20 mL of dichloromethane , Tetrahydrofuran (20 mL) and 2,4,2-trifluoroethylamine (0.44 g, 4.4 mmol) and triethylamine (0.45 g, 4.5 m) under ice-cooling. mol), and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the obtained reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 2) to obtain 0.52 g (yield: 64%) of the desired product.
　1H-NMRデータ(400MHz,DMSO-d6/TMS δ(ppm)): 2.43(3H, s), 4.05-4.09(2H, m), 6.80(2H, s), 6.85(1H, t), 7.46(1H, d), 7.54(1H, d), 9.06(1H, t)  1 H-NMR data (400 MHz, DMSO-d 6 / TMS δ (ppm)): 2.43 (3H, s), 4.05-4.09 (2H, m), 6.80 (2H, s), 6.85 (1H, t), 7.46 (1H, d), 7.54 (1H, d), 9.06 (1H, t)
［実施例４］
　４－フルオロ－２－メチル－５－［５－メチル－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド（本発明の化合物番号：Ａ－０１０２）の製造 [Example 4]
4-fluoro-2-methyl-5- [5-methyl-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -N- (2,2,2-trifluoroethyl ) Preparation of benzoic acid amide (Compound No. of the present invention: A-0102)
　（１）５－［２－（１－アミノ－２，２，２－トリフルオロエチリデン）ヒドラジニル］－４－フルオロ－２－メチル安息香酸エチルの製造
　粗製の５－［２－（１－ブロモ－２，２，２－トリフルオロエチリデン）ヒドラジニル］－４－フルオロ－２－メチル安息香酸エチル２．５８ｇ（６．９５ｍｍｏｌ）のクロロホルム溶液３０ｍＬに、氷冷下、２８％アンモニア水１０ｍＬを加え、室温で１時間撹拌した。反応終了後、クロロホルムを加え、有機層を水にて洗浄し、無水硫酸ナトリウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝４：１～３：１）にて精製し、目的物を１．２７ｇ（収率６０％）得た。 (1) Production of ethyl 5- [2- (1-amino-2,2,2-trifluoroethylidene) hydrazinyl] -4-fluoro-2-methylbenzoate Crude 5- [2- (1-bromo- 10 mL of 28% aqueous ammonia was added to 30 mL of a chloroform solution containing 2.58 g (6.95 mmol) of ethyl 2,2,2-trifluoroethylidene) hydrazinyl] -4-fluoro-2-methylbenzoate under ice-cooling. For 1 hour. After completion of the reaction, chloroform was added, and the organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1 to 3: 1) to obtain 1.27 g of the desired product (yield: 60%). Was.
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 1.38(3H, t), 2.51(3H, s), 4.33(2H, q), 4.47(2H, brs), 6.23(1H, s), 6.89(1H, d), 7.93(1H, d) 1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 1.38 (3H, t), 2.51 (3H, s), 4.33 (2H, q), 4.47 (2H, brs), 6.23 (1H, s), 6.89 (1H, d), 7.93 (1H, d)
　（２）４－フルオロ－２－メチル－５－［５－メチル－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］安息香酸エチル（本発明の化合物番号：Ｃ－０１０９）の製造
　５－［２－（１－アミノ－２，２，２－トリフルオロエチリデン）ヒドラジニル］－４－フルオロ－２－メチル安息香酸エチル１．２７ｇ（４．１３ｍｍｏｌ）のＮ，Ｎ－ジメチルアセトアミド溶液１０ｍＬに、氷冷下、塩化アセチル０．４９ｇ（６．２ｍｍｏｌ）を加え、１４０℃で１時間撹拌した。室温にて放冷後、酢酸エチルを加え、有機層を水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝４：１）にて精製し、目的物を１．１０ｇ（収率８０％）得た。 (2) Ethyl 4-fluoro-2-methyl-5- [5-methyl-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] benzoate (Compound No. of the present invention: Preparation of C-0109) Ethyl 5- [2- (1-amino-2,2,2-trifluoroethylidene) hydrazinyl] -4-fluoro-2-methylbenzoate 1.27 g (4.13 mmol) of N, To 10 mL of the N-dimethylacetamide solution was added 0.49 g (6.2 mmol) of acetyl chloride under ice-cooling, followed by stirring at 140 ° C. for 1 hour. After cooling at room temperature, ethyl acetate was added, and the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1) to obtain 1.10 g (yield: 80%) of the desired product.
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 1.40(3H, t), 2.47(3H, s), 2.72(3H, s), 4.38(2H, q), 7.20(1H, d), 8.09(1H, d) 1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 1.40 (3H, t), 2.47 (3H, s), 2.72 (3H, s), 4.38 (2H, q), 7.20 (1H, d), 8.09 (1H, d)
　（３）４－フルオロ－２－メチル－５－［５－メチル－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］安息香酸（本発明の化合物番号：Ｂ－０１０２）の製造
　４－フルオロ－２－メチル－５－［５－メチル－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］安息香酸エチル１．１０ｇ（３．３２ｍｍｏｌ）の酢酸溶液５ｍＬに、濃塩酸１０ｍＬを加え、１００℃で１９時間撹拌した。室温にて放冷後、水を加え、クロロホルムにて抽出し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、粗製の目的物を１．０２ｇ（収率 定量的）得た。 (3) 4-fluoro-2-methyl-5- [5-methyl-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] benzoic acid (Compound No. B of the present invention) Production of ethyl 4-fluoro-2-methyl-5- [5-methyl-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] benzoate 1.10 g (3 10 mL of concentrated hydrochloric acid was added to 5 mL of an acetic acid solution of 0.32 mmol), and the mixture was stirred at 100 ° C. for 19 hours. After cooling at room temperature, water was added, extracted with chloroform, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.02 g (quantitative yield) of a crude target product.
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 2.48(3H, s), 2.75(3H, s), 7.24(1H, d), 8.22(1H, d) 1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 2.48 (3H, s), 2.75 (3H, s), 7.24 (1H, d), 8.22 (1H, d)
　（４）４－フルオロ－２－メチル－５－［５－メチル－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミドの製造
　４－フルオロ－２－メチル－５－［５－メチル－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］安息香酸０．５０ｇ（１．７ｍｍｏｌ）、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩０．３８ｇ（２．０ｍｍｏｌ）、１－ヒドロキシベンゾトリアゾール一水和物０．３０ｇ（２．０ｍｍｏｌ）、ジクロロメタン２０ｍＬの混合物に、氷冷下、２，２，２－トリフルオロエチルアミン０．３３ｇ（３．３ｍｍｏｌ）、トリエチルアミン０．３３ｇ（３．３ｍｍｏｌ）を加え、室温で１８時間撹拌した。反応終了後、得られた反応混合物を減圧下濃縮し、残渣に酢酸エチルを加え、有機層を飽和炭酸水素ナトリウム水溶液、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝２：１～１：１）にて精製し、目的物を０．５５ｇ（収率８７％）得た。 (4) 4-fluoro-2-methyl-5- [5-methyl-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -N- (2,2,2- Preparation of (trifluoroethyl) benzoic acid amide 4-Fluoro-2-methyl-5- [5-methyl-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] benzoic acid 50 g (1.7 mmol), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 0.38 g (2.0 mmol), 1-hydroxybenzotriazole monohydrate 0.30 g (2.0 mmol), To a mixture of dichloromethane (20 mL) were added 0.32 g (3.3 mmol) of 2,2,2-trifluoroethylamine and 0.33 g (3.3 mmol) of triethylamine under ice-cooling. Stir for 8 hours. After completion of the reaction, the obtained reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1 to 1: 1) to obtain 0.55 g of the desired product (87% yield). Was.
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 2.47(3H, s), 2.56(3H, s), 4.07-4.15(2H, m), 6.11(1H, brs), 7.24(1H, d), 7.55(1H, d)  1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 2.47 (3H, s), 2.56 (3H, s), 4.07-4.15 (2H, m), 6.11 (1H, brs), 7.24 ( 1H, d), 7.55 (1H, d)
［実施例５］
　４－フルオロ－２－メチル－５－［５－メチル－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－Ｎ－［（メチルチオ）メチル］－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド（本発明の化合物番号：Ａ－０７３９）の製造
　４－フルオロ－２－メチル－５－［５－メチル－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド０．５０ｇ（１．３ｍｍｏｌ）のＮ，Ｎ－ジメチルホルムアミド溶液２０ｍＬに、室温下、水素化ナトリウム０．２０ｇ（純度５５％　４．６ｍｍｏｌ）を加え、室温で３０分撹拌した。その後、室温下、クロロメチルメチルスルフィド０．６３ｇ（６．５ｍｍｏｌ）を加え、室温でさらに４時間撹拌した。反応終了後、水を加え、酢酸エチルとヘキサンの混合溶媒にて抽出し、得られた有機層を飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝４：１）にて精製し、目的物を０．２７ｇ（収率４７％）得た。 [Example 5]
4-fluoro-2-methyl-5- [5-methyl-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -N-[(methylthio) methyl] -N- ( Preparation of 2,2,2-trifluoroethyl) benzoic acid amide (Compound No. of the present invention: A-0739) 4-Fluoro-2-methyl-5- [5-methyl-3- (trifluoromethyl) -1H -1,2,4-triazol-1-yl] -N- (2,2,2-trifluoroethyl) benzoic acid amide 0.50 g (1.3 mmol) in N, N-dimethylformamide solution (20 mL) was added at room temperature. Below, 0.20 g (purity 55%, 4.6 mmol) of sodium hydride was added, and the mixture was stirred at room temperature for 30 minutes. Thereafter, 0.63 g (6.5 mmol) of chloromethyl methyl sulfide was added at room temperature, and the mixture was further stirred at room temperature for 4 hours. After completion of the reaction, water was added, and the mixture was extracted with a mixed solvent of ethyl acetate and hexane. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1) to obtain 0.27 g of the desired product (yield: 47%).
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 2.04(3H, ｓ), 2.41(3H, s), 2.47(3H, s), 4.43(4H, ｍ), 7.23(1H, d), 7.36(1H, d) 1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 2.04 (3H, s), 2.41 (3H, s), 2.47 (3H, s), 4.43 (4H, m), 7.23 (1H, d), 7.36 (1H, d)
［実施例６］
　４－フルオロ－２－メチル－５－［５－メチル－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－Ｎ－（２，２，２－トリフルオロエチル）安息香酸チオアミド（本発明の化合物番号：Ａ－０７２７）の製造
　４－フルオロ－２－メチル－５－［５－メチル－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド０．８０ｇ（２．１ｍｍｏｌ）、ローソン試薬０．９４ｇ（２．３ｍｍｏｌ）、トルエン３０ｍＬの混合物を１３．５時間加熱還流した。室温にて放冷後、析出してきた固体を濾過で除去し、濾液を減圧下濃縮した。残渣をシリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝２：１）にて精製し、目的物を０．１４ｇ（収率１７％）得た。 [Example 6]
4-fluoro-2-methyl-5- [5-methyl-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -N- (2,2,2-trifluoroethyl ) Preparation of Benzoic Acid Thioamide (Compound No. of the Invention: A-0727) 4-Fluoro-2-methyl-5- [5-methyl-3- (trifluoromethyl) -1H-1,2,4-triazole- 1-yl] -N- (2,2,2-trifluoroethyl) benzoic acid amide (0.80 g, 2.1 mmol), Lawson's reagent 0.94 g (2.3 mmol), and toluene (30 mL) were mixed for 13.5 hours. Heated to reflux. After cooling at room temperature, the precipitated solid was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, n-hexane: ethyl acetate = 2: 1) to obtain 0.14 g (yield 17%) of the desired product.
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 2.47(3H, s), 2.49(3H, d), 4.56-4.64(2H, m), 7.19(1H, d), 7.38(1H, brs), 7.44(1H, d) 1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 2.47 (3H, s), 2.49 (3H, d), 4.56-4.64 (2H, m), 7.19 (1H, d), 7.38 ( 1H, brs), 7.44 (1H, d)
［実施例７］
　５－［５－クロロ－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド（本発明の化合物番号：Ａ－０１９５）の製造
　５－［５－アミノ－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド１．００ｇ（２．６０ｍｍｏｌ）、塩化銅（ＩＩ）０．７０ｇ（５．２ｍｍｏｌ）、アセトニトリル２０ｍＬの混合物に、氷冷下、亜硝酸ｔｅｒｔ－ブチル０．５４ｇ（５．２ｍｍｏｌ）を加え、室温で４時間撹拌した。反応終了後、酢酸エチルを加え、有機層を水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝２：１）にて精製し、目的物を０．８６ｇ（収率８２％）得た。 [Example 7]
5- [5-chloro-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl-N- (2,2,2-trifluoroethyl ) Preparation of benzoic acid amide (Compound No. A-0195 of the present invention) 5- [5-amino-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro To a mixture of -2-methyl-N- (2,2,2-trifluoroethyl) benzoic acid amide 1.00 g (2.60 mmol), copper (II) chloride 0.70 g (5.2 mmol) and acetonitrile 20 mL, Under ice-cooling, tert-butyl nitrite (0.54 g, 5.2 mmol) was added, and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 0.86 g (yield: 82%) of the desired product.
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 2.57(3H, s), 4.09-4.13(2H, m), 6.10(1H, s), 7.25(1H, d), 7.55(1H, d)  1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 2.57 (3H, s), 4.09-4.13 (2H, m), 6.10 (1H, s), 7.25 (1H, d), 7.55 ( 1H, d)
［実施例８］
　４－フルオロ－５－［５－メトキシ－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド（本発明の化合物番号：Ａ－０２１２）の製造
　５－［５－クロロ－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド０．５５ｇ（１．４ｍｍｏｌ）のメタノール溶液２０ｍＬに、炭酸カリウム０．２３ｇ（１．７ｍｍｏｌ）を加え、室温で４時間撹拌した。反応終了後、得られた反応混合物を減圧下濃縮し、残渣をシリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝２：１）にて精製し、目的物を０．４７ｇ（収率８６％）得た。 Example 8
4-fluoro-5- [5-methoxy-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -2-methyl-N- (2,2,2-trifluoroethyl ) Preparation of benzoic acid amide (Compound No. A-0212 of the present invention) 5- [5-chloro-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro 0.23 g (1.7 mmol) of potassium carbonate was added to 20 mL of a methanol solution of 0.55 g (1.4 mmol) of -2-methyl-N- (2,2,2-trifluoroethyl) benzoic acid amide, and the mixture was added at room temperature. Stir for 4 hours. After completion of the reaction, the obtained reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 0.47 g of the desired product (yield). 86%).
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 2.52(3H, s), 4.06-4.14(2H, m), 4.19(3H, s), 6.09(1H, brs), 7.17(1H, d), 7.53(1H, d)  1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 2.52 (3H, s), 4.06-4.14 (2H, m), 4.19 (3H, s), 6.09 (1H, brs), 7.17 ( 1H, d), 7.53 (1H, d)
［実施例９］
　４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）－５－［３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］安息香酸アミド（本発明の化合物番号：Ａ－００６２）の製造
　５－［５－アミノ－３－（トリフルオロメチル）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド０．２２ｇ（０．５７ｍｍｏｌ）のテトラヒドロフラン溶液１５ｍＬに、亜硝酸ｔｅｒｔ－ブチル０．０７ｇ（０．６８ｍｍｏｌ）を加え、４時間加熱還流した。室温にて放冷後、得られた反応混合物を減圧下濃縮し、残渣をシリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝１：１）にて精製し、目的物を０．１６ｇ（収率７６％）得た。 [Example 9]
4-fluoro-2-methyl-N- (2,2,2-trifluoroethyl) -5- [3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] benzoic acid amide Preparation of (Compound No. A-0062 of the Present Invention) 5- [5-Amino-3- (trifluoromethyl) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl To a solution of 0.22 g (0.57 mmol) of -N- (2,2,2-trifluoroethyl) benzoic acid amide in 15 mL of tetrahydrofuran was added 0.07 g (0.68 mmol) of tert-butyl nitrite, and the mixture was heated for 4 hours. Refluxed. After cooling at room temperature, the obtained reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 1) to obtain 0.16 g of the desired product (76% yield).
　1H-NMRデータ(400MHz,DMSO-d6/TMS δ(ppm)): 2.43(3H, s), 4.05-4.14(2H, m), 7.59(1H, d), 7.83(1H, d), 9.18(1H, t), 9.35(1H, s)  1 H-NMR data (400 MHz, DMSO-d 6 / TMS δ (ppm)): 2.43 (3H, s), 4.05-4.14 (2H, m), 7.59 (1H, d), 7.83 (1H, d), 9.18 (1H, t), 9.35 (1H, s)
［実施例１０］
　４－フルオロ－５－［３－（１，１，２，３，３，３－ヘキサフルオロプロポキシ）－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル］－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド（本発明の化合物番号：Ａ－１０４３）の製造 [Example 10]
4-fluoro-5- [3- (1,1,2,3,3,3-hexafluoropropoxy) -5-methyl-1H-1,2,4-triazol-1-yl] -2-methyl- Production of N- (2,2,2-trifluoroethyl) benzoic acid amide (Compound No. of the present invention: A-1043)
　（１）１－（２－フルオロ－４－メチルフェニル）セミカルバジドの製造
　米国特許公報ＵＳ２００９／０１５６６４２号記載の方法に準じて製造した（２－フルオロ－４－メチルフェニル）ヒドラジン６．００ｇ（４２．８ｍｍｏｌ）の２Ｍ塩酸溶液１００ｍＬに、シアン酸カリウム７．７２ｇ（純度９０％　８５．７ｍｍｏｌ）を加え、室温で３．５時間撹拌した後、さらにシアン酸ナトリウム１０．８２ｇ（純度９０％　１４９．８ｍｍｏｌ）を加え、室温で２．５時間撹拌した。析出した固体をろ過、水洗、乾燥させ、粗製の目的物を５．４３ｇ（収率６９％）得た。
　1H-NMRデータ(300MHz,DMSO-d6/TMS δ(ppm)): 2.15(3H, s), 5.90(2H, brs), 6.67(1H, t), 6.78-6.86(2H, m), 7.34(1H, brs), 7.64(1H, brs) (1) Production of 1- (2-fluoro-4-methylphenyl) semicarbazide 6.00 g of (2-fluoro-4-methylphenyl) hydrazine produced according to the method described in US Patent Publication US2009 / 0156642 (42. 8.72 g (purity 90%, 85.7 mmol) of potassium cyanate was added to 100 mL of a 2M hydrochloric acid solution (8 mmol), and the mixture was stirred at room temperature for 3.5 hours. ) And stirred at room temperature for 2.5 hours. The precipitated solid was filtered, washed with water, and dried to obtain 5.43 g (yield: 69%) of a crude target product.
1 H-NMR data (300 MHz, DMSO-d 6 / TMS δ (ppm)): 2.15 (3H, s), 5.90 (2H, brs), 6.67 (1H, t), 6.78-6.86 (2H, m), 7.34 (1H, brs), 7.64 (1H, brs)
　（２）１－（２－フルオロ－４－メチルフェニル）－５－メチル－１Ｈ－１，２，４－トリアゾール－３－オール（本発明の化合物番号：Ｄ－２０１９）の製造
　１－（２－フルオロ－４－メチルフェニル）セミカルバジド５．４３ｇ（２９．６ｍｍｏｌ）、ｐ－トルエンスルホン酸一水和物０．５６ｇ（２．９ｍｍｏｌ）、オルト酢酸トリエチル５０ｍＬの混合物を１００℃で４．５時間撹拌した。室温にて放冷後、得られた反応混合物を減圧下濃縮し、得られた粗生成物をジイソプロピルエーテルで洗浄し、目的物を５．４１ｇ（収率８８％）得た。
　1H-NMRデータ(300MHz,DMSO-d6/TMS δ(ppm)): 2.13(3H, d), 2.35(3H, s), 7.14(1H, d), 7.28(1H, dd), 7.41(1H, t), 11.03(1H, brs) (2) Production of 1- (2-fluoro-4-methylphenyl) -5-methyl-1H-1,2,4-triazol-3-ol (Compound No. D-2019 of the present invention) 1- (2) A mixture of 5.43 g (29.6 mmol) of -fluoro-4-methylphenyl) semicarbazide, 0.56 g (2.9 mmol) of p-toluenesulfonic acid monohydrate and 50 mL of triethyl orthoacetate at 100 ° C. for 4.5 hours. Stirred. After cooling at room temperature, the obtained reaction mixture was concentrated under reduced pressure, and the obtained crude product was washed with diisopropyl ether to obtain 5.41 g of the desired product (yield: 88%).
1 H-NMR data (300 MHz, DMSO-d 6 / TMS δ (ppm)): 2.13 (3H, d), 2.35 (3H, s), 7.14 (1H, d), 7.28 (1H, dd), 7.41 ( 1H, t), 11.03 (1H, brs)
　（３）１－（２－フルオロ－４－メチルフェニル）－３－（１，１，２，３，３，３－ヘキサフルオロプロポキシ）－５－メチル－１Ｈ－１，２，４－トリアゾール（本発明の化合物番号：Ｄ－２０２３）の製造
　１－（２－フルオロ－４－メチルフェニル）－５－メチル－１Ｈ－１，２，４－トリアゾール－３－オール２．４０ｇ（１１．６ｍｍｏｌ）、トリエチルアミン１０ｍＬ、Ｎ，Ｎ－ジメチルホルムアミド５０ｍＬの混合物に、氷冷下、ヘキサフルオロプロペン８．５０ｇ（５６．７ｍｍｏｌ）を吹き込み、室温で１６時間撹拌した。反応終了後、酢酸エチルを加え、有機層を希塩酸、水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝４：１）にて精製し、目的物を２．２１ｇ（収率５３％）得た。
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 2.36(3H, d), 2.43(3H, s), 5.18-5.43(1H, m), 7.06-7.10(2H, m), 7.32(1H, t) (3) 1- (2-fluoro-4-methylphenyl) -3- (1,1,2,3,3,3-hexafluoropropoxy) -5-methyl-1H-1,2,4-triazole ( Preparation of Compound No. D-2023) of the Invention 2.40 g (11.6 mmol) of 1- (2-fluoro-4-methylphenyl) -5-methyl-1H-1,2,4-triazol-3-ol 8.50 g (56.7 mmol) of hexafluoropropene was blown into a mixture of 10 mL of triethylamine and 50 mL of N, N-dimethylformamide under ice cooling, followed by stirring at room temperature for 16 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with dilute hydrochloric acid, water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1) to obtain 2.21 g of the desired product (yield 53%).
1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 2.36 (3H, d), 2.43 (3H, s), 5.18-5.43 (1H, m), 7.06-7.10 (2H, m), 7.32 (1H, t)
　（４）１－（２－フルオロ－５－ヨード－４－メチルフェニル）－３－（１，１，２，３，３，３－ヘキサフルオロプロポキシ）－５－メチル－１Ｈ－１，２，４－トリアゾール（本発明の化合物番号：Ｄ－１０１９）の製造
　１－（２－フルオロ－４－メチルフェニル）－３－（１，１，２，３，３，３－ヘキサフルオロプロポキシ）－５－メチル－１Ｈ－１，２，４－トリアゾール２．１２ｇ（５．９３ｍｍｏｌ）の濃硫酸溶液１５ｍＬに、氷冷下、Ｎ－ヨードコハク酸イミド１．４０ｇ（６．２２ｍｍｏｌ）を加え、氷冷下５時間撹拌した。反応終了後、反応溶液を氷水にあけ、酢酸エチルで抽出し、有機層を水、１Ｎチオ硫酸ナトリウム水溶液、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、粗製の目的物を２．６９ｇ（収率９４％）得た。
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 2.38(3H, d), 2.49(3H, s), 5.17-5.41(1H, m), 7.17(1H, d), 7.88(1H, d) (4) 1- (2-Fluoro-5-iodo-4-methylphenyl) -3- (1,1,2,3,3,3-hexafluoropropoxy) -5-methyl-1H-1,2,2 Preparation of 4-triazole (Compound No. of the Invention: D-1019) 1- (2-fluoro-4-methylphenyl) -3- (1,1,2,3,3,3-hexafluoropropoxy) -5 To 15 mL of a concentrated sulfuric acid solution of 2.12 g (5.93 mmol) of -methyl-1H-1,2,4-triazole was added 1.40 g (6.22 mmol) of N-iodosuccinimide under ice cooling, and the mixture was cooled under ice. Stir for 5 hours. After completion of the reaction, the reaction solution was poured into ice water, extracted with ethyl acetate, and the organic layer was washed with water, a 1N aqueous solution of sodium thiosulfate, and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 2.69 g (yield 94%) of a crude target product.
1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 2.38 (3H, d), 2.49 (3H, s), 5.17-5.41 (1H, m), 7.17 (1H, d), 7.88 ( 1H, d)
　（５）４－フルオロ－５－［３－（１，１，２，３，３，３－ヘキサフルオロプロポキシ）－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル］－２－メチルベンゾニトリル（本発明の化合物番号：Ｄ－００１８）の製造
　１－（２－フルオロ－５－ヨード－４－メチルフェニル）－３－（１，１，２，３，３，３－ヘキサフルオロプロポキシ）－５－メチル－１Ｈ－１，２，４－トリアゾール２．６９ｇ（５．５７ｍｍｏｌ）のＮ，Ｎ－ジメチルアセトアミド溶液２０ｍＬに、シアン化銅（Ｉ）１．２５ｇ（１４．０ｍｍｏｌ）を加え、１００℃で２２．５時間撹拌した。室温にて放冷後、酢酸エチルを加え、有機層をアンモニア水、水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝４：３）にて精製し、目的物を１．９４ｇ（収率９１％）得た。
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 2.39(3H, d), 2.65(3H, s), 5.16-5.40(1H, m), 7.28(1H, d), 7.77(1H, d) (5) 4-fluoro-5- [3- (1,1,2,3,3,3-hexafluoropropoxy) -5-methyl-1H-1,2,4-triazol-1-yl] -2 Preparation of 1- (2-fluoro-5-iodo-4-methylphenyl) -3- (1,1,2,3,3,3-hexa-methylbenzonitrile (Compound No. D-0018 of the present invention) 1.25 g (14.0 mmol) of copper (I) cyanide was added to a solution of 2.69 g (5.57 mmol) of (fluoropropoxy) -5-methyl-1H-1,2,4-triazole in 20 mL of N, N-dimethylacetamide. Was added and stirred at 100 ° C. for 22.5 hours. After cooling at room temperature, ethyl acetate was added, and the organic layer was washed with aqueous ammonia, water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 3) to obtain 1.94 g (yield: 91%) of the desired product.
1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 2.39 (3H, d), 2.65 (3H, s), 5.16-5.40 (1H, m), 7.28 (1H, d), 7.77 ( 1H, d)
　（６）４－フルオロ－５－［３－（１，１，２，３，３，３－ヘキサフルオロプロポキシ）－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル］－２－メチル安息香酸（本発明の化合物番号：Ｂ－１０３５）の製造
　４－フルオロ－５－［３－（１，１，２，３，３，３－ヘキサフルオロプロポキシ）－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル］－２－メチルベンゾニトリル１．８５ｇ（４．８４ｍｍｏｌ）、１，４－ジオキサン１ｍＬ、６０％硫酸１２ｍＬの混合物を１００℃で２０時間撹拌した。室温にて放冷後、酢酸エチルを加え、有機層を水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、粗製の目的物を１．９８ｇ（収率 定量的）得た。
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 2.40(3H, d), 2.73(3H, s), 5.17-5.42(1H, m), 7.21(1H, d), 8.21(1H, d) (6) 4-fluoro-5- [3- (1,1,2,3,3,3-hexafluoropropoxy) -5-methyl-1H-1,2,4-triazol-1-yl] -2 Preparation of -methylbenzoic acid (Compound No. B-1035 of the present invention) 4-Fluoro-5- [3- (1,1,2,3,3,3-hexafluoropropoxy) -5-methyl-1H- A mixture of 1.85 g (4.84 mmol) of 1,2,4-triazol-1-yl] -2-methylbenzonitrile, 1 mL of 1,4-dioxane, and 12 mL of 60% sulfuric acid was stirred at 100 ° C. for 20 hours. After cooling at room temperature, ethyl acetate was added, and the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.98 g (quantitative yield) of a crude target product.
1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 2.40 (3H, d), 2.73 (3H, s), 5.17-5.42 (1H, m), 7.21 (1H, d), 8.21 ( 1H, d)
　（７）４－フルオロ－５－［３－（１，１，２，３，３，３－ヘキサフルオロプロポキシ）－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル］－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミドの製造
　４－フルオロ－５－［３－（１，１，２，３，３，３－ヘキサフルオロプロポキシ）－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル］－２－メチル安息香酸０．６０ｇ（１．５ｍｍｏｌ）、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩０．３５ｇ（１．８ｍｍｏｌ）、１－ヒドロキシベンゾトリアゾール一水和物０．２８ｇ（１．８ｍｍｏｌ）、テトラヒドロフラン２０ｍＬの混合物に、氷冷下、２，２，２－トリフルオロエチルアミン０．２２ｇ（２．２ｍｍｏｌ）、Ｎ，Ｎ－ジイソプロピルエチルアミン０．２３ｇ（１．８ｍｍｏｌ）を加え、室温で９６時間撹拌した。反応終了後、得られた反応混合物を減圧下濃縮し、残渣に酢酸エチルを加え、有機層を飽和炭酸水素ナトリウム水溶液、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。
溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝１：１）にて精製し、目的物を０．６２ｇ（収率８６％）得た。
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 2.38(3H, d), 2.52(3H, s), 4.03-4.14(2H, m), 5.16-5.40(1H, m), 6.21(1H, t), 7.19 (1H, d), 7.52(1H, d) (7) 4-fluoro-5- [3- (1,1,2,3,3,3-hexafluoropropoxy) -5-methyl-1H-1,2,4-triazol-1-yl] -2 Preparation of -methyl-N- (2,2,2-trifluoroethyl) benzoic acid amide 4-fluoro-5- [3- (1,1,2,3,3,3-hexafluoropropoxy) -5 Methyl-1H-1,2,4-triazol-1-yl] -2-methylbenzoic acid 0.60 g (1.5 mmol), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 0.35 g (1.8 mmol), 0.28 g (1.8 mmol) of 1-hydroxybenzotriazole monohydrate and 20 mL of tetrahydrofuran were added under ice cooling to 0.22 g (2.2 mmol) of 2,2,2-trifluoroethylamine. ) And 0.23 g (1.8 mmol) of N, N-diisopropylethylamine were added, and the mixture was stirred at room temperature for 96 hours. After completion of the reaction, the obtained reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and brine, and dried over anhydrous magnesium sulfate.
The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 1) to obtain 0.62 g (yield: 86%) of the desired product.
1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 2.38 (3H, d), 2.52 (3H, s), 4.03-4.14 (2H, m), 5.16-5.40 (1H, m), 6.21 (1H, t), 7.19 (1H, d), 7.52 (1H, d)
［実施例１１］
　５－［５－アミノ－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド（本発明の化合物番号：Ａ－２１７０）の製造
　（１）Ｎ－シアノジチオカルボンイミノ酸ジ（２，２，２－トリフルオロエチル）の製造
　国際公開特許公報ＷＯ１９９４／０２６７０６号記載の方法に準じて製造したＮ－シアノジチオカルボンイミノ酸二カリウム７．００ｇ（３６．０ｍｍｏｌ）のジメチルスルホキシド溶液５０ｍＬに、氷冷下、トリフルオロメタンスルホン酸２，２，２－トリフルオロエチル２０．０６ｇ（８６．４３ｍｍｏｌ）を加え、室温で６７時間撹拌した。反応終了後、酢酸エチルを加え、有機層を水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、粗製の目的物を６．８１ｇ（収率６７％）得た。
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 3.93(4H, q) [Example 11]
5- [5-amino-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl-N- (2 Production of 2,2-trifluoroethyl) benzoic acid amide (Compound No. A-2170 of the present invention) (1) Production of di (2,2,2-trifluoroethyl) N-cyanodithiocarboxyimino acid International publication Trifluoromethanesulfonic acid 2,2,2 was added to 50 mL of a dimethyl sulfoxide solution of 7.00 g (36.0 mmol) of dipotassium N-cyanodithiocarboxyiminoate prepared according to the method described in Patent Publication WO 1994/026706 under ice-cooling. 20.06 g (86.43 mmol) of 2-trifluoroethyl was added, and the mixture was stirred at room temperature for 67 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 6.81 g (yield 67%) of a crude target product.
1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 3.93 (4H, q)
　（２）５－［５－アミノ－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸エチル（本発明の化合物番号：Ｃ－２１５８）の製造
　４－フルオロ－５－ヒドラジニル－２－メチル安息香酸エチル４．９７ｇ（２３．４ｍｍｏｌ）のエタノール溶液１４０ｍＬに、Ｎ－シアノジチオカルボンイミノ酸ジ（２，２，２－トリフルオロエチル）６．８１ｇ（２４．１ｍｍｏｌ）を加え、５．５時間加熱還流した。室温にて放冷後、得られた反応混合物を減圧下濃縮し、残渣をシリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝１：１）にて精製し、目的物を５．４９ｇ（収率６２％）得た。
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 1.38(3H, t), 2.66(3H, s), 3.79(2H, q), 4.35(2H, q), 4.58(2H, brs), 7.15(1H, d), 8.09(1H, d) (2) Ethyl 5- [5-amino-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoate Preparation of (Compound No. C-2158 of the present invention) N-cyanodithiocarboxylic imino acid di () was added to 140 mL of an ethanol solution of 4.97 g (23.4 mmol) of ethyl 4-fluoro-5-hydrazinyl-2-methylbenzoate in ethanol. 6.81 g (24.1 mmol) of 2,2,2-trifluoroethyl) was added, and the mixture was heated under reflux for 5.5 hours. After cooling at room temperature, the obtained reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 1) to obtain 5.49 g of the desired product. (62% yield).
1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 1.38 (3H, t), 2.66 (3H, s), 3.79 (2H, q), 4.35 (2H, q), 4.58 (2H, brs), 7.15 (1H, d), 8.09 (1H, d)
　（３）５－［５－アミノ－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸（本発明の化合物番号：Ｂ－２１４３）の製造
　５－［５－アミノ－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸エチル５．４９ｇ（１４．５ｍｍｏｌ）、エタノール１５ｍＬ、テトラヒドロフラン５０ｍＬ、水２５ｍＬの混合物に、水酸化リチウム一水和物１．８３ｇ（４３．６ｍｍｏｌ）を加え、室温で３時間撹拌した。反応終了後、酢酸エチルを加え、有機層を２Ｎ塩酸、水、飽和食塩水にて洗浄し、無水硫酸ナトリウムにて乾燥した。溶媒を減圧下留去して、粗製の目的物を５．５６ｇ（収率 定量的）得た。
　1H-NMRデータ(300MHz,DMSO-d6/TMS δ(ppm)): 2.56(3H, s), 4.00(2H, q), 6.70(2H, brs), 7.42(1H, d), 7.84(1H, d) (3) 5- [5-amino-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoic acid ( Preparation of Compound No. B-2143) of the Present Invention 5- [5-Amino-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazol-1-yl] -4 1.83 g (43.6 mmol) of lithium hydroxide monohydrate was added to a mixture of 5.49 g (14.5 mmol) of ethyl-fluoro-2-methylbenzoate, 15 mL of ethanol, 50 mL of tetrahydrofuran and 25 mL of water, and the mixture was added at room temperature. Stir for 3 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with 2N hydrochloric acid, water, and saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 5.56 g (quantitative yield) of a crude target product.
1 H-NMR data (300 MHz, DMSO-d 6 / TMS δ (ppm)): 2.56 (3H, s), 4.00 (2H, q), 6.70 (2H, brs), 7.42 (1H, d), 7.84 ( 1H, d)
　（４）５－［５－アミノ－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミドの製造
　５－［５－アミノ－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸３．００ｇ（８．５６ｍｍｏｌ）、トリフルオロエチルアミン３．３９ｇ（３４．２ｍｍｏｌ）、１－ヒドロキシベンゾトリアゾール一水和物２．６２ｇ（１７．１ｍｍｏｌ）、Ｎ，Ｎ－ジイソプロピルエチルアミン２．２１ｇ（１７．１ｍｍｏｌ）、テトラヒドロフラン６０ｍＬの混合物に、氷冷下、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩３．２８ｇ（１７．１ｍｍｏｌ）を加え、室温で６３時間撹拌した。反応終了後、得られた反応混合物を減圧下濃縮し、残渣に酢酸エチルを加え、有機層を飽和炭酸水素ナトリウム水溶液、飽和食塩水にて洗浄し、無水硫酸ナトリウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、クロロホルム：メタノール＝１０：１～５：１）にて精製し、目的物を２．８９ｇ（収率７８％）得た。
　1H-NMRデータ(300MHz,DMSO-d6/TMS δ(ppm)): 2.37(3H, s), 3.95-4.09(4H, m), 6.70(2H, brs), 7.38(1H, d), 7.45(1H, d), 9.01(1H, t) (4) 5- [5-amino-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl-N- Production of (2,2,2-trifluoroethyl) benzoic acid amide 5- [5-amino-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazole-1- Yl] -4-fluoro-2-methylbenzoic acid 3.00 g (8.56 mmol), trifluoroethylamine 3.39 g (34.2 mmol), 1-hydroxybenzotriazole monohydrate 2.62 g (17.1 mmol) To a mixture of 2.21 g (17.1 mmol) of N, N-diisopropylethylamine and 60 mL of tetrahydrofuran, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide was added under ice-cooling. 3.28 g (17.1 mmol) of hydrochloride was added, and the mixture was stirred at room temperature for 63 hours. After completion of the reaction, the obtained reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate and brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, chloroform: methanol = 10: 1 to 5: 1) to obtain 2.89 g of the desired product (yield 78%).
1 H-NMR data (300 MHz, DMSO-d 6 / TMS δ (ppm)): 2.37 (3H, s), 3.95-4.09 (4H, m), 6.70 (2H, brs), 7.38 (1H, d), 7.45 (1H, d), 9.01 (1H, t)
［実施例１２］
　５－［３－（ジフルオロメチルチオ）－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド（本発明の化合物番号：Ａ－２１１４）の製造
　（１）５－（３－アミノ－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル）－４－フルオロ－２－メチル安息香酸エチル（本発明の化合物番号：Ｃ－２３１９）の製造
　Ｓ－メチルイソチオウレアヨウ化水素酸塩８．２２ｇ（３７．７ｍｍｏｌ）のテトラヒドロフラン溶液５０ｍＬに、氷冷下、トリエチルアミン９．５４ｇ（９４．３ｍｍｏｌ）、塩化アセチル２．９６ｇ（３７．７ｍｍｏｌ）を加え、室温で３０分間撹拌した。得られた反応混合物に氷冷下、４－フルオロ－５－ヒドラジニル－２－メチル安息香酸エチル４．００ｇ（１８．９ｍｍｏｌ）のテトラヒドロフラン溶液２０ｍＬを滴下し、２時間加熱還流した。室温まで放冷後、酢酸エチルを加え、有機層を水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、エタノール４０ｍＬ、濃硫酸１ｍＬを加え、一晩加熱還流した。室温にて放冷後、飽和炭酸水素ナトリウム溶液、酢酸エチルを加え、有機層を水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、析出した結晶を酢酸エチル、ｎ－ヘキサンで洗浄し、目的物を２．７４ｇ（収率５２％）得た。
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 1.38(3H, t), 2.29(3H, d), 2.67(3H, s), 4.20(2H, brs), 4.35(2H, q), 7.13(1H, d), 8.06(1H, d) [Example 12]
5- [3- (difluoromethylthio) -5-methyl-1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl-N- (2,2,2-trifluoroethyl) Production of benzoic acid amide (Compound No. A-2114 of the present invention) (1) 5- (3-amino-5-methyl-1H-1,2,4-triazol-1-yl) -4-fluoro-2 -Production of ethyl methylbenzoate (Compound No. C-2319 of the present invention) 9.54 g of triethylamine was added to 50 mL of a tetrahydrofuran solution of 8.22 g (37.7 mmol) of S-methylisothiourea hydroiodide under ice-cooling. (94.3 mmol) and 2.96 g (37.7 mmol) of acetyl chloride were added, and the mixture was stirred at room temperature for 30 minutes. To the obtained reaction mixture was added dropwise a solution of 4.00 g (18.9 mmol) of ethyl 4-fluoro-5-hydrazinyl-2-methylbenzoate in 20 mL of tetrahydrofuran under ice-cooling, and the mixture was refluxed for 2 hours. After allowing to cool to room temperature, ethyl acetate was added, and the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, 40 mL of ethanol and 1 mL of concentrated sulfuric acid were added, and the mixture was heated under reflux overnight. After allowing to cool at room temperature, a saturated sodium hydrogen carbonate solution and ethyl acetate were added, and the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the precipitated crystals were washed with ethyl acetate and n-hexane to obtain 2.74 g of the desired product (yield: 52%).
1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 1.38 (3H, t), 2.29 (3H, d), 2.67 (3H, s), 4.20 (2H, brs), 4.35 (2H, q), 7.13 (1H, d), 8.06 (1H, d)
　（２）４－フルオロ－２－メチル－５－［５－メチル－３－（メチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］安息香酸エチル（本発明の化合物番号：Ｃ－２００９）の製造
　５－（３－アミノ－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル）－４－フルオロ－２－メチル安息香酸エチル２１．１１ｇ（７５．８６ｍｍｏｌ）、ジメチルジスルフィド１４．２９ｇ（１５１．７ｍｍｏｌ）、クロロホルム１５０ｍＬの混合物に、氷冷下、亜硝酸ｔｅｒｔ－ブチル１７．３８ｇ（１６８．５ｍｍｏｌ）を加え、室温で２４時間撹拌した。得られた反応混合物を減圧下濃縮し、残渣をシリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝４：３）にて精製し、目的物を１４．９６ｇ（収率６４％）得た。
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 1.37(3H, t), 2.35(3H, d), 2.60(3H, s), 2.67(3H, s), 4.34(2H, q), 7.14(1H, d), 8.06(1H, d) (2) Ethyl 4-fluoro-2-methyl-5- [5-methyl-3- (methylthio) -1H-1,2,4-triazol-1-yl] benzoate (Compound No. of the present invention: C- 2009) Ethyl 5- (3-amino-5-methyl-1H-1,2,4-triazol-1-yl) -4-fluoro-2-methylbenzoate 21.11 g (75.86 mmol), dimethyl To a mixture of 14.29 g (151.7 mmol) of disulfide and 150 mL of chloroform was added 17.38 g (168.5 mmol) of tert-butyl nitrite under ice cooling, and the mixture was stirred at room temperature for 24 hours. The obtained reaction mixture is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent, n-hexane: ethyl acetate = 4: 3) to obtain 14.96 g of the desired product (yield 64%). Was.
1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 1.37 (3H, t), 2.35 (3H, d), 2.60 (3H, s), 2.67 (3H, s), 4.34 (2H, q), 7.14 (1H, d), 8.06 (1H, d)
　（３）４－フルオロ－２－メチル－５－［５－メチル－３－（メチルスルフィニル）－１Ｈ－１，２，４－トリアゾール－１－イル］安息香酸エチル（本発明の化合物番号：Ｃ－２０１１）の製造
　４－フルオロ－２－メチル－５－［５－メチル－３－（メチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］安息香酸エチル１５．９０ｇ（５１．４０ｍｍｏｌ）のジクロロメタン溶液１２０ｍＬに、氷冷下、ｍ－クロロ過安息香酸１３．２４ｇ（純度：約６５％、４９．０２ｍｍｏｌ）を加え、２時間撹拌した。反応終了後、反応溶液中に１Ｎチオ硫酸ナトリウム水溶液を加え、過剰な過酸化物を分解した。その後、酢酸エチルを加え、有機層を飽和炭酸水素ナトリウム水溶液、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝１：４～１：１０）にて精製し、目的物を１３．４３ｇ（収率８０％）得た。
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 1.37(3H, t), 2.45(3H, d), 2.67(3H, s), 3.05(3H, s), 4.34(2H, q), 7.18(1H, d), 8.11(1H, d) (3) Ethyl 4-fluoro-2-methyl-5- [5-methyl-3- (methylsulfinyl) -1H-1,2,4-triazol-1-yl] benzoate (Compound No. of the present invention: C Preparation of -2011) 15.90 g (51.40 mmol) of ethyl 4-fluoro-2-methyl-5- [5-methyl-3- (methylthio) -1H-1,2,4-triazol-1-yl] benzoate 13.24 g (purity: about 65%, 49.02 mmol) of m-chloroperbenzoic acid was added to 120 mL of a dichloromethane solution of) under ice cooling, and the mixture was stirred for 2 hours. After completion of the reaction, a 1N aqueous solution of sodium thiosulfate was added to the reaction solution to decompose excess peroxide. Thereafter, ethyl acetate was added, and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 4 to 1:10) to obtain 13.43 g of the desired product (80% yield). Was.
1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 1.37 (3H, t), 2.45 (3H, d), 2.67 (3H, s), 3.05 (3H, s), 4.34 (2H, q), 7.18 (1H, d), 8.11 (1H, d)
　（４）４－フルオロ－５－（３－メルカプト－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル）－２－メチル安息香酸メチル（本発明の化合物番号：Ｃ－２００２）の製造
　４－フルオロ－２－メチル－５－［５－メチル－３－（メチルスルフィニル）－１Ｈ－１，２，４－トリアゾール－１－イル］安息香酸エチル１３．４３ｇ（４１．２８ｍｍｏｌ）のクロロホルム溶液１５０ｍＬに、トリフルオロ酢酸無水物５２．０２ｇ（２４７．７ｍｍｏｌ）を加え、室温で１４時間撹拌した。溶媒を減圧下留去して、残渣をメタノール１００ｍＬに溶解した。氷冷下、炭酸カリウム１７．１２ｇ（１２３．９ｍｍｏｌ）を加え、室温で５．５時間撹拌した。塩酸を加えｐＨ５に調整した後、飽和食塩水を加え、酢酸エチルで抽出し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、粗製の目的物を得た。精製することなく、このまま次の工程に用いた。
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 2.44(3H, d), 2.70(3H, s), 3.90(3H, s), 7.19(1H, d), 8.08(1H, d) (4) Methyl 4-fluoro-5- (3-mercapto-5-methyl-1H-1,2,4-triazol-1-yl) -2-methylbenzoate (Compound No. C-2002 of the present invention) Preparation of 13.43 g (41.28 mmol) of ethyl 4-fluoro-2-methyl-5- [5-methyl-3- (methylsulfinyl) -1H-1,2,4-triazol-1-yl] benzoate 52.02 g (247.7 mmol) of trifluoroacetic anhydride was added to 150 mL of a chloroform solution, and the mixture was stirred at room temperature for 14 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in 100 mL of methanol. Under ice-cooling, 17.12 g (123.9 mmol) of potassium carbonate was added, and the mixture was stirred at room temperature for 5.5 hours. After adjusting the pH to 5 by adding hydrochloric acid, saturated saline was added, and the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude target product. This was used for the next step without purification.
1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 2.44 (3H, d), 2.70 (3H, s), 3.90 (3H, s), 7.19 (1H, d), 8.08 (1H, d)
　（５）５－［３－（ジフルオロメチルチオ）－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸メチル（本発明の化合物番号：Ｃ－２１１１）の製造
　粗製の４－フルオロ－５－（３－メルカプト－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル）－２－メチル安息香酸メチル１．２０ｇ（純度：約６３％、２．６９ｍｍｏｌ）、炭酸カリウム０．５６ｇ（４．１ｍｍｏｌ）、ロンガリット０．２１ｇ（１．４ｍｍｏｌ）、Ｎ，Ｎ－ジメチルホルムアミド１０ｍＬの混合物に、クロロジフルオロメタンを吹き込み、６０℃で５時間撹拌した。反応終了後、酢酸エチルを加え、有機層を水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝３：２）にて精製し、目的物を０．４２ｇ（収率４７％）得た。
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 2.40(3H, d), 2.69(3H, s), 3.89(3H, s), 7.14(1H, d), 7.46(1H, t), 8.07(1H, d) (5) Methyl 5- [3- (difluoromethylthio) -5-methyl-1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoate (Compound No .: C of the present invention) Production of crude 4-fluoro-5- (3-mercapto-5-methyl-1H-1,2,4-triazol-1-yl) -2-methylbenzoate 1.20 g (purity: approx. Chlorodifluoromethane was blown into a mixture of 63%, 2.69 mmol), 0.56 g (4.1 mmol) of potassium carbonate, 0.21 g (1.4 mmol) of Rongalite, and 10 mL of N, N-dimethylformamide. Stirred for hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3: 2) to obtain 0.42 g of the desired product (yield 47%).
1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 2.40 (3H, d), 2.69 (3H, s), 3.89 (3H, s), 7.14 (1H, d), 7.46 (1H, t), 8.07 (1H, d)
　（６）５－［３－（ジフルオロメチルチオ）－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸（本発明の化合物番号：Ｂ－２０９８）の製造
　５－［３－（ジフルオロメチルチオ）－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸メチル０．４２ｇ（１．３ｍｍｏｌ）、エタノール５ｍＬ、テトラヒドロフラン１０ｍＬ、水５ｍＬの混合物に、水酸化リチウム一水和物０．１６ｇ（３．８ｍｍｏｌ）を加え、室温で１時間撹拌した。反応終了後、得られた反応混合物を減圧下濃縮し、残渣に酢酸エチルを加え、有機層を希クエン酸水溶液、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、粗製の目的物を０．４５ｇ（収率 定量的）得た。
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 2.43(3H, d), 2.75(3H, s), 7.23(1H, d), 7.47(1H, t), 8.21(1H, d) (6) 5- [3- (difluoromethylthio) -5-methyl-1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoic acid (Compound No. of the present invention: B- 2098) Methyl 5- [3- (difluoromethylthio) -5-methyl-1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoate 0.42 g (1.3 mmol) ), Ethanol 5 mL, tetrahydrofuran 10 mL, and water 5 mL, 0.16 g (3.8 mmol) of lithium hydroxide monohydrate was added, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the obtained reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the organic layer was washed with a dilute aqueous citric acid solution and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.45 g (quantitative yield) of a crude target product.
1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 2.43 (3H, d), 2.75 (3H, s), 7.23 (1H, d), 7.47 (1H, t), 8.21 (1H, d)
　（７）５－［３－（ジフルオロメチルチオ）－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミドの製造
　５－［３－（ジフルオロメチルチオ）－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル安息香酸０．２１ｇ（０．６６ｍｍｏｌ）、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩０．１５ｇ（０．７８ｍｍｏｌ）、１－ヒドロキシベンゾトリアゾール一水和物０．１２ｇ（０．７８ｍｍｏｌ）、テトラヒドロフラン１５ｍＬの混合物に、氷冷下、２，２，２－トリフルオロエチルアミン０．１０ｇ（１．０ｍｍｏｌ）、Ｎ，Ｎ－ジイソプロピルエチルアミン０．１０ｇ（０．９９ｍｍｏｌ）を加え、室温で１８時間撹拌した。反応終了後、得られた反応混合物を減圧下濃縮し、残渣に酢酸エチルを加え、有機層を飽和炭酸水素ナトリウム水溶液、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝１：２）にて精製し、目的物を０．２１ｇ（収率８０％）得た。
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 2.40(3H, d), 2.53(3H, s), 4.03-4.14(2H, m), 6.18(1H, t), 7.19 (1H, d), 7.43(1H, t), 7.52(1H, d) (7) 5- [3- (difluoromethylthio) -5-methyl-1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl-N- (2,2,2-tri Preparation of (fluoroethyl) benzoic acid amide 5- [3- (difluoromethylthio) -5-methyl-1H-1,2,4-triazol-1-yl] -4-fluoro-2-methylbenzoic acid 0.21 g ( 0.66 mmol), 0.15 g (0.78 mmol) of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 0.12 g (0.78 mmol) of 1-hydroxybenzotriazole monohydrate, 15 mL of tetrahydrofuran Under ice-cooling, 0.10 g (1.0 mmol) of 2,2,2-trifluoroethylamine and 0.10 g of N, N-diisopropylethylamine ( 0.99 mmol) and stirred at room temperature for 18 hours. After completion of the reaction, the obtained reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 2) to obtain 0.21 g of the desired product (80% yield).
1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 2.40 (3H, d), 2.53 (3H, s), 4.03-4.14 (2H, m), 6.18 (1H, t), 7.19 ( 1H, d), 7.43 (1H, t), 7.52 (1H, d)
［実施例１３］
　５－［３－クロロ－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド（本発明の化合物番号：Ａ－２４５３）の製造
　（１）５－（３－クロロ－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル）－４－フルオロ－２－メチル安息香酸エチル（本発明の化合物番号：Ｃ－２３４２）の製造
　５－（３－アミノ－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル）－４－フルオロ－２－メチル安息香酸エチル１．００ｇ（３．５９ｍｍｏｌ）、塩化銅（ＩＩ）０．９７ｇ（７．２ｍｍｏｌ）、アセトニトリル１０ｍＬの混合物に、氷冷下、亜硝酸ｔｅｒｔ－ブチル０．８２ｇ（７．２ｍｍｏｌ）のアセトニトリル溶液５ｍＬを加え、２時間撹拌した。反応終了後、酢酸エチルを加え、有機層を水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝２：１）にて精製し、目的物を０．５８ｇ（収率５４％）得た。
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 1.39(3H, t), 2.40(3H, d), 2.70(3H, s), 4.37(2H, q), 7.18(1H, d), 8.08(1H, d) Example 13
5- [3-chloro-5-methyl-1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl-N- (2,2,2-trifluoroethyl) benzoic acid amide Preparation of (Compound No. A-2453 of the present invention) (1) 5- (3-chloro-5-methyl-1H-1,2,4-triazol-1-yl) -4-fluoro-2-methylbenzoic acid Of ethyl acetate (Compound No. C-2342 of the present invention) 5- (3-Amino-5-methyl-1H-1,2,4-triazol-1-yl) -4-fluoro-2-methylbenzoic acid To a mixture of 1.00 g (3.59 mmol) of ethyl, 0.97 g (7.2 mmol) of copper (II) chloride and 10 mL of acetonitrile, a solution of 0.82 g (7.2 mmol) of tert-butyl nitrite in acetonitrile under ice cooling. Add 5 mL , And the mixture was stirred for 2 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 0.58 g (yield: 54%) of the desired product.
1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 1.39 (3H, t), 2.40 (3H, d), 2.70 (3H, s), 4.37 (2H, q), 7.18 (1H, d), 8.08 (1H, d)
　（２）５－(３－クロロ－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル)－４－フルオロ－２－メチル安息香酸（本発明の化合物番号：Ｂ－２３２０）の製造
　５－（３－クロロ－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル）－４－フルオロ－２－メチル安息香酸エチル０．４４ｇ（１．５ｍｍｏｌ）、メタノール１０ｍＬ、テトラヒドロフラン１０ｍＬ、水１０ｍＬの混合物に、水酸化リチウム一水和物０．３１ｇ（７．４ｍｍｏｌ）を加え、室温で一晩撹拌した。反応終了後、酢酸エチルを加え、有機層を２Ｎ塩酸、水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。
溶媒を減圧下留去して、析出した結晶をジイソプロピルエーテルで洗浄し、目的物を０．２５ｇ（収率６３％）得た。
　1H-NMRデータ(400MHz,DMSO-d6/TMS δ(ppm)): 2.34(3H, s), 2.63(3H, s), 7.57(1H, d), 8.10(1H, d), 13.31(1H, brs) (2) 5- (3-chloro-5-methyl-1H-1,2,4-triazol-1-yl) -4-fluoro-2-methylbenzoic acid (Compound No. B-2320 of the present invention) Production Ethyl 5- (3-chloro-5-methyl-1H-1,2,4-triazol-1-yl) -4-fluoro-2-methylbenzoate 0.44 g (1.5 mmol), methanol 10 mL, tetrahydrofuran To a mixture of 10 mL and 10 mL of water was added 0.31 g (7.4 mmol) of lithium hydroxide monohydrate, and the mixture was stirred at room temperature overnight. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with 2N hydrochloric acid, water, and saturated saline, and dried over anhydrous magnesium sulfate.
The solvent was distilled off under reduced pressure, and the precipitated crystals were washed with diisopropyl ether to obtain 0.25 g (yield: 63%) of the desired product.
1 H-NMR data (400 MHz, DMSO-d 6 / TMS δ (ppm)): 2.34 (3H, s), 2.63 (3H, s), 7.57 (1H, d), 8.10 (1H, d), 13.31 ( 1H, brs)
　（３）５－［３－クロロ－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル］－４－フルオロ－２－メチル－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミドの製造
　５－(３－クロロ－５－メチル－１Ｈ－１，２，４－トリアゾール－１－イル)－４－フルオロ－２－メチル安息香酸０．２５ｇ（０．９３ｍｍｏｌ）のジクロロメタン溶液１０ｍＬに２，２，２－トリフルオロエチルアミン０．１１ｇ（１．１ｍｍｏｌ）、１－ヒドロキシベンゾトリアゾール一水和物０．１３ｇ（０．８５ｍｍｏｌ）、１－エチル－３－（３－ジメチルアミノプロピル）カルボジイミド塩酸塩０．２１ｇ（１．１ｍｍｏｌ）を加えた。氷冷下、トリエチルアミン０．２３ｇ（２．３ｍｍｏｌ）を加え、室温で一晩撹拌した。反応終了後、酢酸エチルを加え、有機層を水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、析出した結晶をｎ－ヘキサンで洗浄し、目的物を０．２５ｇ（収率７７％）得た。
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 2.39(3H, d), 2.54(3H, s), 4.04-4.14(2H, m), 6.52(1H, t), 7.19(1H, d), 7.54(1H, d) (3) 5- [3-chloro-5-methyl-1H-1,2,4-triazol-1-yl] -4-fluoro-2-methyl-N- (2,2,2-trifluoroethyl) Preparation of benzoic acid amide 5- (3-chloro-5-methyl-1H-1,2,4-triazol-1-yl) -4-fluoro-2-methylbenzoic acid 0.25 g (0.93 mmol) of dichloromethane 0.12 g (1.1 mmol) of 2,2,2-trifluoroethylamine, 0.13 g (0.85 mmol) of 1-hydroxybenzotriazole monohydrate, 1-ethyl-3- (3-dimethylamino) in 10 mL of the solution Propyl) carbodiimide hydrochloride 0.21 g (1.1 mmol) was added. Under ice cooling, 0.23 g (2.3 mmol) of triethylamine was added, and the mixture was stirred at room temperature overnight. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the precipitated crystals were washed with n-hexane to obtain 0.25 g (yield 77%) of the desired product.
1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 2.39 (3H, d), 2.54 (3H, s), 4.04-4.14 (2H, m), 6.52 (1H, t), 7.19 ( 1H, d), 7.54 (1H, d)
［実施例１４］
　４－フルオロ－２－メチル－５－［５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミド（本発明の化合物番号：Ａ－２２６１）の製造
　（１）５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾールの製造
　Ｉｎｄｉａｎ　Ｊ．Ｃｈｅｍ．Ｓｅｃ．Ｂ，３８Ｂ巻，１８頁～２３頁（１９９９年）記載の方法に準じて製造した５－メチル－１，２－ジヒドロ－３Ｈ－１，２，４－トリアゾール－３－チオン４．００ｇ（３４．７ｍｍｏｌ）、炭酸カリウム５．７６ｇ（４１．７ｍｍｏｌ）、ロンガリット１．６１ｇ（１０．５ｍｍｏｌ）、Ｎ，Ｎ－ジメチルホルムアミド２０ｍＬの混合物に、１，１，１－トリフルオロ－２－ヨードエタン１４．５９ｇ（６９．５０ｍｍｏｌ）を加え、４０℃で３日間撹拌した。反応終了後、酢酸エチルを加え、有機層を希炭酸水素ナトリウム水溶液、飽和食塩水にて洗浄し、無水硫酸ナトリウムにて乾燥した。溶媒を減圧下留去して、粗製の目的物を６．０４ｇ（収率８８％）得た。
　1H-NMRデータ(400MHz,DMSO-d6/TMS δ(ppm)): 2.33(3H, s), 4.07(2H, q), 13.77(1H, brs) [Example 14]
4-fluoro-2-methyl-5- [5-methyl-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazol-1-yl] -N- (2 Production of 2,2-trifluoroethyl) benzoic acid amide (Compound No. A-2261 of the present invention) (1) 5-Methyl-3- (2,2,2-trifluoroethylthio) -1H-1, Preparation of 2,4-triazole Indian J. Chem. Sec. B, 38B, pp. 18-23 (1999), 4.00 g of 5-methyl-1,2-dihydro-3H-1,2,4-triazol-3-thione (34) 0.71 mmol), 5.76 g (41.7 mmol) of potassium carbonate, 1.61 g (10.5 mmol) of Rongalit, and 20 mL of N, N-dimethylformamide, and 1,1,1-trifluoro-2-iodoethane. 59 g (69.50 mmol) was added, and the mixture was stirred at 40 ° C. for 3 days. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with a dilute aqueous sodium hydrogen carbonate solution and saturated saline, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 6.04 g (88% yield) of a crude target product.
1 H-NMR data (400 MHz, DMSO-d 6 / TMS δ (ppm)): 2.33 (3H, s), 4.07 (2H, q), 13.77 (1H, brs)
　（２）３－フルオロ－４－［５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］ベンズアルデヒド（本発明の化合物番号：Ｄ－２０３２）の製造
　５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール３．００ｇ（１５．２ｍｍｏｌ）、３，４－ジフルオロベンズアルデヒド３．２４ｇ（２２．８ｍｍｏｌ）、炭酸カリウム３．１５ｇ（２２．８ｍｍｏｌ）、アセトニトリル１８ｍＬの混合物を２．５時間加熱還流した。室温にて放冷後、酢酸エチルとｎ－ヘキサンを加え、不溶物をセライト濾過した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝２：１）にて精製し、目的物を２．６８ｇ（収率５５％）得た。
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 2.44(3H, d), 3.86(2H, q), 7.70(1H, t), 7.79-7.86(2H, m), 10.06(1H, s) (2) 3-fluoro-4- [5-methyl-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazol-1-yl] benzaldehyde (compound number of the present invention) : D-2032) 5-methyl-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazole 3.00 g (15.2 mmol), 3,4-difluorobenzaldehyde A mixture of 3.24 g (22.8 mmol), 3.15 g (22.8 mmol) of potassium carbonate, and 18 mL of acetonitrile was heated under reflux for 2.5 hours. After cooling at room temperature, ethyl acetate and n-hexane were added, and the insolubles were filtered through celite. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 2.68 g of the desired product (55% yield).
1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 2.44 (3H, d), 3.86 (2H, q), 7.70 (1H, t), 7.79-7.86 (2H, m), 10.06 ( 1H, s)
　（３）｛３－フルオロ－４－［５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］フェニル｝メタノール（本発明の化合物番号：Ｄ－２０３３）の製造
　水素化ホウ素ナトリウム０．４４ｇ（１２ｍｍｏｌ）のテトラヒドロフラン溶液１０ｍＬに、氷冷下、３－フルオロ－４－［５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］ベンズアルデヒド２．６８ｇ（８．３９ｍｍｏｌ）のテトラヒドロフラン溶液１０ｍＬを加え、２時間撹拌した。反応終了後、反応溶液中に１Ｎ塩酸を加え、過剰な水素化ホウ素ナトリウムを分解した。その後、酢酸エチルで抽出し、有機層を飽和炭酸水素ナトリウム水溶液、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝１：２）にて精製し、目的物を２．０７ｇ（収率７７％）得た。
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 2.37(3H, d), 3.84(2H, q), 4.79(2H, s), 7.22-7.33(2H, m), 7.42(1H, t) (3) {3-fluoro-4- [5-methyl-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazol-1-yl] phenyl} methanol (the present invention Preparation of Compound No. D-2033) To a solution of 0.44 g (12 mmol) of sodium borohydride in 10 mL of tetrahydrofuran was added 3-fluoro-4- [5-methyl-3- (2,2,2-) under ice-cooling. A solution of 2.68 g (8.39 mmol) of trifluoroethylthio) -1H-1,2,4-triazol-1-yl] benzaldehyde in 10 mL of tetrahydrofuran was added, and the mixture was stirred for 2 hours. After completion of the reaction, 1N hydrochloric acid was added to the reaction solution to decompose excess sodium borohydride. Thereafter, the mixture was extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 2) to obtain 2.07 g (yield 77%) of the desired product.
1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 2.37 (3H, d), 3.84 (2H, q), 4.79 (2H, s), 7.22-7.33 (2H, m), 7.42 ( 1H, t)
　（４）１－［４－（クロロメチル）－２－フルオロフェニル］－５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール（本発明の化合物番号：Ｄ－２０３４）の製造
　｛３－フルオロ－４－［５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］フェニル｝メタノール２．０７ｇ（６．４４ｍｍｏｌ）、四塩化炭素７．９０ｇ（５１．４ｍｍｏｌ）、テトラヒドロフラン２０ｍＬの混合物に、室温下、トリフェニルホスフィン３．３８ｇ（１２．９ｍｍｏｌ）を加え、５０℃で３時間撹拌した後、さらに２時間加熱還流した。室温にて放冷後、ジイソプロピルエーテルと酢酸エチルを加え、不溶物をセライト濾過した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝２：１）にて精製し、目的物を１．６８ｇ（収率７７％）得た。
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 2.38(3H, d), 3.84(2H, q), 4.61(2H, s), 7.30-7.35(2H, m), 7.45(1H, t) (4) 1- [4- (chloromethyl) -2-fluorophenyl] -5-methyl-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazole (the present invention Compound No .: D-2034) {3-fluoro-4- [5-methyl-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazol-1-yl To a mixture of 2.07 g (6.44 mmol) of phenyl @ methanol, 7.90 g (51.4 mmol) of carbon tetrachloride and 20 mL of tetrahydrofuran, 3.38 g (12.9 mmol) of triphenylphosphine was added at room temperature, and the mixture was heated at 50 ° C. After stirring for 3 hours, the mixture was heated and refluxed for another 2 hours. After cooling at room temperature, diisopropyl ether and ethyl acetate were added, and the insolubles were filtered through celite. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 1.68 g of the desired product (yield: 77%).
1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 2.38 (3H, d), 3.84 (2H, q), 4.61 (2H, s), 7.30-7.35 (2H, m), 7.45 ( 1H, t)
　（５）１－（２－フルオロ－４－メチルフェニル）－５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール（本発明の化合物番号：Ｄ－２０２８）の製造
　１－［４－（クロロメチル）－２－フルオロフェニル］－５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール１．５５ｇ（４．５６ｍｍｏｌ）のジメチルスルホキシド溶液１８ｍＬに、氷冷下、水素化ホウ素ナトリウム０．１７ｇ（４．５ｍｍｏｌ）を加え、室温で４時間撹拌した。さらに水素化ホウ素ナトリウム０．０３ｇ（０．８ｍｍｏｌ）を加え、室温で１時間撹拌した。反応終了後、反応溶液中に１Ｎ塩酸を加え、過剰な水素化ホウ素ナトリウムを分解した。その後、酢酸エチルで抽出し、有機層を水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、粗製の目的物を１．６０ｇ（収率 定量的）得た。
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 2.48(3H, s), 2.52(3H, s), 3.84(2H, q), 7.10-7.18(2H, m), 7.32(1H, t) (5) 1- (2-fluoro-4-methylphenyl) -5-methyl-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazole (compound number of the present invention) : D-2028) 1- [4- (Chloromethyl) -2-fluorophenyl] -5-methyl-3- (2,2,2-trifluoroethylthio) -1H-1,2,4- To 18 mL of a dimethyl sulfoxide solution of 1.55 g (4.56 mmol) of triazole was added 0.17 g (4.5 mmol) of sodium borohydride under ice-cooling, followed by stirring at room temperature for 4 hours. Further, 0.03 g (0.8 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 1N hydrochloric acid was added to the reaction solution to decompose excess sodium borohydride. Thereafter, the mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.60 g (quantitative yield) of a crude target product.
1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 2.48 (3H, s), 2.52 (3H, s), 3.84 (2H, q), 7.10-7.18 (2H, m), 7.32 ( 1H, t)
　（６）１－（２－フルオロ－５－ヨード－４－メチルフェニル）－５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール（本発明の化合物番号：Ｄ－１０２１）の製造
　１－（２－フルオロ－４－メチルフェニル）－５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール１．６０ｇ（５．２４ｍｍｏｌ）の濃硫酸溶液１８ｍＬに、氷冷下、Ｎ－ヨードコハク酸イミド１．１８ｇ（５．２４ｍｍｏｌ）を加え、氷冷下７時間撹拌した。さらにＮ－ヨードコハク酸イミド０．９４ｇ（４．２ｍｍｏｌ）を加え、室温で１７時間撹拌した。反応終了後、反応溶液を氷水にあけ、酢酸エチルで抽出し、有機層を水、１Ｎチオ硫酸ナトリウム水溶液、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、粗製の目的物を１．９３ｇ（収率８５％）得た。
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 2.36(3H, d), 2.49(3H, s), 3.83(2H, q), 7.16(1H, d), 7.85(1H, d) (6) 1- (2-fluoro-5-iodo-4-methylphenyl) -5-methyl-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazole (this Preparation of Compound No. D-1021) of the Invention 1- (2-Fluoro-4-methylphenyl) -5-methyl-3- (2,2,2-trifluoroethylthio) -1H-1,2,4 To 18 mL of a concentrated sulfuric acid solution of 1.60 g (5.24 mmol) of -triazole was added 1.18 g (5.24 mmol) of N-iodosuccinimide under ice cooling, and the mixture was stirred for 7 hours under ice cooling. Further, 0.94 g (4.2 mmol) of N-iodosuccinimide was added, and the mixture was stirred at room temperature for 17 hours. After completion of the reaction, the reaction solution was poured into ice water, extracted with ethyl acetate, and the organic layer was washed with water, a 1N aqueous solution of sodium thiosulfate, and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.93 g (yield: 85%) of a crude target product.
1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 2.36 (3H, d), 2.49 (3H, s), 3.83 (2H, q), 7.16 (1H, d), 7.85 (1H, d)
　（７）４－フルオロ－２－メチル－５－［５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］ベンゾニトリル（本発明の化合物番号：Ｄ－００２０）の製造
　１－（２－フルオロ－５－ヨード－４－メチルフェニル）－５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール１．９３ｇ（４．４８ｍｍｏｌ）のＮ，Ｎ－ジメチルアセトアミド溶液１８ｍＬに、シアン化銅（Ｉ）０．８０ｇ（８．９ｍｍｏｌ）を加え、１００℃で１６時間撹拌した。室温にて放冷後、酢酸エチルと水を加え、不溶物をセライト濾過した。有機層を１Ｎ塩酸、水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝１：１）にて精製し、目的物を１．２６ｇ（収率８５％）得た。
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 2.38(3H, d), 2.64(3H, s), 3.83(2H, q), 7.26(1H, d), 7.75(1H, d) (7) 4-fluoro-2-methyl-5- [5-methyl-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazol-1-yl] benzonitrile ( Preparation of Compound No. D-0020) of the Present Invention 1- (2-Fluoro-5-iodo-4-methylphenyl) -5-methyl-3- (2,2,2-trifluoroethylthio) -1H- To a solution of 1.93 g (4.48 mmol) of 1,2,4-triazole in 18 mL of N, N-dimethylacetamide was added 0.80 g (8.9 mmol) of copper (I) cyanide, and the mixture was stirred at 100 ° C. for 16 hours. . After cooling at room temperature, ethyl acetate and water were added, and the insolubles were filtered through celite. The organic layer was washed with 1N hydrochloric acid, water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 1) to obtain 1.26 g (yield: 85%) of the desired product.
1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 2.38 (3H, d), 2.64 (3H, s), 3.83 (2H, q), 7.26 (1H, d), 7.75 (1H, d)
　（８）４－フルオロ－２－メチル－５－［５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］安息香酸（本発明の化合物番号：Ｂ－２１８９）の製造
　４－フルオロ－２－メチル－５－［５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］ベンゾニトリル１．２６ｇ（３．８１ｍｍｏｌ）、１，４－ジオキサン５ｍＬ、６０％硫酸３６ｍＬの混合物を１００℃で２０．５時間撹拌した。室温にて放冷後、酢酸エチルを加え、有機層を水、希塩酸、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、粗製の目的物を１．３２ｇ（収率９９％）得た。
　1H-NMRデータ(400MHz,CDCl3/TMS δ(ppm)): 2.41(3H, d), 2.74(3H, s), 3.85(2H, q), 7.21(1H, d), 8.20(1H, d) (8) 4-fluoro-2-methyl-5- [5-methyl-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazol-1-yl] benzoic acid ( Preparation of Compound No. B-2189) of the Present Invention 4-Fluoro-2-methyl-5- [5-methyl-3- (2,2,2-trifluoroethylthio) -1H-1,2,4- A mixture of 1.26 g (3.81 mmol) of [triazol-1-yl] benzonitrile, 5 mL of 1,4-dioxane and 36 mL of 60% sulfuric acid was stirred at 100 ° C. for 20.5 hours. After cooling at room temperature, ethyl acetate was added, and the organic layer was washed with water, diluted hydrochloric acid and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.32 g (yield: 99%) of a crude target product.
1 H-NMR data (400 MHz, CDCl 3 / TMS δ (ppm)): 2.41 (3H, d), 2.74 (3H, s), 3.85 (2H, q), 7.21 (1H, d), 8.20 (1H, d)
　（９）４－フルオロ－２－メチル－５－［５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］－Ｎ－（２，２，２－トリフルオロエチル）安息香酸アミドの製造
　４－フルオロ－２－メチル－５－［５－メチル－３－（２，２，２－トリフルオロエチルチオ）－１Ｈ－１，２，４－トリアゾール－１－イル］安息香酸３．００ｇ（８．５９ｍｍｏｌ）、Ｎ，Ｎ－ジメチルホルムアミド０．０６ｇ（０．８ｍｍｏｌ）、クロロホルム２０ｍＬの混合物に、塩化オキサリル１．３１ｇ（１０．３ｍｍｏｌ）を加え、室温で１．５時間撹拌した。反応終了後、溶媒を減圧下留去して、残渣をクロロホルム２０ｍＬに溶解し、氷冷下、２，２，２－トリフルオロエチルアミン１．７０ｇ（１７．２ｍｍｏｌ）、トリエチルアミン１．７４ｇ（１７．２ｍｍｏｌ）、クロロホルム２０ｍＬの混合物に加え、室温で一晩撹拌した。反応終了後、クロロホルムを加え、有機層を水、飽和食塩水にて洗浄し、無水硫酸マグネシウムにて乾燥した。溶媒を減圧下留去して、シリカゲルカラムクロマトグラフィー（展開溶媒、ｎ－ヘキサン：酢酸エチル＝３：１～１：１）にて精製し、目的物を２．９１ｇ（収率７９％）得た。
　1H-NMRデータ(300MHz,CDCl3/TMS δ(ppm)): 2.36(3H, d), 2.52(3H, s), 3.83(2H, q), 4.03-4.14(2H, q), 6.16(1H, t), 7.17(1H, d), 7.50(1H, d) (9) 4-Fluoro-2-methyl-5- [5-methyl-3- (2,2,2-trifluoroethylthio) -1H-1,2,4-triazol-1-yl] -N- Preparation of (2,2,2-trifluoroethyl) benzoic acid amide 4-Fluoro-2-methyl-5- [5-methyl-3- (2,2,2-trifluoroethylthio) -1H-1, 2,4-Triazol-1-yl] benzoic acid (3.00 g, 8.59 mmol), N, N-dimethylformamide (0.06 g, 0.8 mmol) and chloroform (20 mL) were mixed in a mixture of 1.31 g (10.10 g) of chloroform. 3 mmol) and stirred at room temperature for 1.5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in 20 mL of chloroform, and under ice-cooling, 1.70 g (17.2 mmol) of 2,2,2-trifluoroethylamine and 1.74 g of triethylamine (17. 2 mmol) and chloroform (20 mL), and the mixture was stirred at room temperature overnight. After completion of the reaction, chloroform was added, and the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3: 1 to 1: 1) to obtain 2.91 g of the desired product (yield 79%). Was.
1 H-NMR data (300 MHz, CDCl 3 / TMS δ (ppm)): 2.36 (3H, d), 2.52 (3H, s), 3.83 (2H, q), 4.03-4.14 (2H, q), 6.16 ( 1H, t), 7.17 (1H, d), 7.50 (1H, d)
　前記実施例に準じて製造した本発明の化合物［Ｉ］の物性値（融点、屈折率及び１Ｈ－ＮＭＲスペクトルデータ）を、前記実施例における値を含め以下の表５９～表７０に示し、製造中間体である本発明の化合物［ＩＩ］の物性値を、前記実施例における値を含め以下の表７１～表８４に示し、製造中間体である本発明の化合物［ＩＩＩ］の物性値を、前記実施例における値を含め以下の表８５～表９０に示す。尚、表中の化合物番号及び記号は、前記と同様の意味を表す。 The physical properties (melting point, refractive index and 1 H-NMR spectrum data) of the compound [I] of the present invention produced according to the above Examples, including the values in the above Examples, are shown in Tables 59 to 70 below. The physical properties of the compound [II] of the present invention, which is a production intermediate, including the values in the above Examples, are shown in Tables 71 to 84 below. Tables 85 to 90 below include the values in the above Examples. The compound numbers and symbols in the table have the same meaning as described above.
Figure JPOXMLDOC01-appb-T000095
Figure JPOXMLDOC01-appb-T000095
Figure JPOXMLDOC01-appb-T000096
Figure JPOXMLDOC01-appb-T000096
Figure JPOXMLDOC01-appb-T000097
Figure JPOXMLDOC01-appb-T000097
Figure JPOXMLDOC01-appb-T000098
Figure JPOXMLDOC01-appb-T000098
Figure JPOXMLDOC01-appb-T000099
Figure JPOXMLDOC01-appb-T000099
Figure JPOXMLDOC01-appb-T000100
Figure JPOXMLDOC01-appb-T000100
Figure JPOXMLDOC01-appb-T000101
Figure JPOXMLDOC01-appb-T000101
Figure JPOXMLDOC01-appb-T000102
Figure JPOXMLDOC01-appb-T000102
Figure JPOXMLDOC01-appb-T000103
Figure JPOXMLDOC01-appb-T000103
Figure JPOXMLDOC01-appb-T000104
Figure JPOXMLDOC01-appb-T000104
Figure JPOXMLDOC01-appb-T000105
Figure JPOXMLDOC01-appb-T000105
Figure JPOXMLDOC01-appb-T000106
Figure JPOXMLDOC01-appb-T000106
Figure JPOXMLDOC01-appb-T000107
Figure JPOXMLDOC01-appb-T000107
Figure JPOXMLDOC01-appb-T000108
Figure JPOXMLDOC01-appb-T000108
Figure JPOXMLDOC01-appb-T000109
Figure JPOXMLDOC01-appb-T000109
Figure JPOXMLDOC01-appb-T000110
Figure JPOXMLDOC01-appb-T000110
Figure JPOXMLDOC01-appb-T000111
Figure JPOXMLDOC01-appb-T000111
Figure JPOXMLDOC01-appb-T000112
Figure JPOXMLDOC01-appb-T000112
Figure JPOXMLDOC01-appb-T000113
Figure JPOXMLDOC01-appb-T000113
Figure JPOXMLDOC01-appb-T000114
Figure JPOXMLDOC01-appb-T000114
Figure JPOXMLDOC01-appb-T000115
Figure JPOXMLDOC01-appb-T000115
Figure JPOXMLDOC01-appb-T000116
Figure JPOXMLDOC01-appb-T000116
Figure JPOXMLDOC01-appb-T000117
Figure JPOXMLDOC01-appb-T000117
Figure JPOXMLDOC01-appb-T000118
Figure JPOXMLDOC01-appb-T000118
Figure JPOXMLDOC01-appb-T000119
Figure JPOXMLDOC01-appb-T000119
Figure JPOXMLDOC01-appb-T000120
Figure JPOXMLDOC01-appb-T000120
Figure JPOXMLDOC01-appb-T000121
Figure JPOXMLDOC01-appb-T000121
Figure JPOXMLDOC01-appb-T000122
Figure JPOXMLDOC01-appb-T000122
Figure JPOXMLDOC01-appb-T000123
Figure JPOXMLDOC01-appb-T000123
Figure JPOXMLDOC01-appb-T000124
Figure JPOXMLDOC01-appb-T000124
Figure JPOXMLDOC01-appb-T000125
Figure JPOXMLDOC01-appb-T000125
Figure JPOXMLDOC01-appb-T000126
Figure JPOXMLDOC01-appb-T000126
　次に、以上のようにして製造された本発明の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農薬上許容される塩を使用した、本発明の有害生物防除剤の製剤例について具体的に説明する。但し、化合物、添加剤の種類及び配合比率は、これのみに限定されることなく広い範囲で変更可能である。又、以下の説明において「部」は質量部を意味する。 Next, the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative of the present invention produced as described above or a pesticidally acceptable salt thereof of the present invention is used. A formulation example of the pesticidal agent will be specifically described. However, the types and compounding ratios of the compounds and additives are not limited to these and can be changed in a wide range. In the following description, “parts” means parts by mass.
［製剤例１］　　　乳剤
　　表１～表２５及び表５９～表７０に記載の化合物　　　　　　　１０部
　　シクロヘキサノン　　　　　　　　　　　　　　　　　　　　　３０部
　　ポリオキシエチレンアルキルアリールエーテル　　　　　　　　１１部
　　アルキルベンゼンスルホン酸カルシウム　　　　　　　　　　　　４部
　　メチルナフタリン　　　　　　　　　　　　　　　　　　　　　４５部
　以上を均一に溶解して乳剤とした。 [Formulation Example 1] Emulsion Compounds described in Tables 1 to 25 and 59 to 70 10 parts Cyclohexanone 30 parts Polyoxyethylene alkylaryl ether 11 parts Calcium alkylbenzenesulfonate 4 parts Methylnaphthalene 45 parts To obtain an emulsion.
［製剤例２］　　　水和剤
　　表１～表２５及び表５９～表７０に記載の化合物　　　　　　　１０部
　　ナフタレンスルホン酸ホルマリン縮合物ナトリウム塩　　　　０．５部
　　ポリオキシエチレンアルキルアリールエーテル　　　　　　　０．５部
　　珪藻土　　　　　　　　　　　　　　　　　　　　　　　　　　２４部
　　クレー　　　　　　　　　　　　　　　　　　　　　　　　　　６５部
　以上を均一に混合粉砕して水和剤とした。 [Formulation Example 2] Water dispersant 10 parts of compounds described in Tables 1 to 25 and 59 to 70 0.5 part sodium salt of formalin condensate of naphthalenesulfonic acid 0.5 part polyoxyethylene alkylaryl ether 0.5 part diatomaceous earth 24 parts 65 parts or more of clay were uniformly mixed and pulverized to obtain a wettable powder.
［製剤例３］　　　粉剤
　　表１～表２５及び表５９～表７０に記載の化合物　　　　　　　　２部
　　珪藻土　　　　　　　　　　　　　　　　　　　　　　　　　　　５部
　　クレー　　　　　　　　　　　　　　　　　　　　　　　　　　９３部
　以上を均一に混合粉砕して粉剤とした。 [Formulation Example 3] Dust The compounds described in Tables 1 to 25 and 59 to 70 2 parts Diatomaceous earth 5 parts Clay 93 parts The above components were uniformly mixed and pulverized to obtain a dust.
［製剤例４］　　　粒剤
　　表１～表２５及び表５９～表７０に記載の化合物　　　　　　　　５部
　　ラウリルアルコール硫酸エステルのナトリウム塩　　　　　　　　２部
　　リグニンスルホン酸ナトリウム　　　　　　　　　　　　　　　　５部
　　カルボキシメチルセルロース　　　　　　　　　　　　　　　　　２部
　　クレー　　　　　　　　　　　　　　　　　　　　　　　　　　８６部
　以上を均一に混合粉砕した。この混合物に水２０部相当量を加えて練り合せ、押出式造粒機を用いて１４～３２メッシュの粒状に加工した後、乾燥して粒剤とした。 Formulation Example 4 Granules Compounds listed in Tables 1 to 25 and 59 to 70 5 parts Sodium salt of lauryl alcohol sulfate 2 parts Sodium lignin sulfonate 5 parts Carboxymethyl cellulose 2 parts Clay 86 parts It was mixed and ground. 20 parts of water was added to the mixture, and the mixture was kneaded, processed into granules of 14 to 32 mesh using an extrusion granulator, and dried to obtain granules.
［製剤例５］　　　フロアブル剤
　　表１～表２５及び表５９～表７０に記載の化合物　　　　　　　２０部
　　ポリオキシエチレンスチレン化フェニルエーテル硫酸塩　　　　　４部
　　エチレングリコール　　　　　　　　　　　　　　　　　　　　　７部
　　シリコーンＡＦ－１１８Ｎ（旭化成工業株式会社製）　　　０．０２部
　　水　　　　　　　　　　　　　　　　　　　　　　　　　６８．９８部
　以上を高速攪拌機にて３０分間混合した後、湿式粉砕機にて粉砕しフロアブル剤とした。 [Formulation Example 5] Flowable agent Compounds listed in Tables 1 to 25 and 59 to 70 20 parts Polyoxyethylene styrenated phenyl ether sulfate 4 parts Ethylene glycol 7 parts Silicone AF-118N (manufactured by Asahi Kasei Corporation) After mixing 0.02 parts of water and 68.98 parts of the above with a high-speed stirrer for 30 minutes, the mixture was pulverized with a wet pulverizer to obtain a flowable agent.
［製剤例６］　　　顆粒水和剤
　　表１～表２５に記載の化合物　　　　　　　　　　　　　　　　１０部
　　リグニンスルホン酸ナトリウム　　　　　　　　　　　　　　　　５部
　　ポリオキシエチレンアルキルアリールエーテル　　　　　　　　　１部
　　ポリカルボン酸ナトリウム　　　　　　　　　　　　　　　　　　３部
　　ホワイトカーボン　　　　　　　　　　　　　　　　　　　　　　５部
　　α化デンプン　　　　　　　　　　　　　　　　　　　　　　　　１部
　　炭酸カルシウム　　　　　　　　　　　　　　　　　　　　　　６５部
　　水　　　　　　　　　　　　　　　　　　　　　　　　　　　　１０部 [Formulation Example 6] Water dispersible granules 10 parts of the compounds shown in Tables 1 to 25 10 parts of sodium ligninsulfonate 5 parts of polyoxyethylene alkylaryl ether 1 part of sodium 3 parts of white carbon 5 parts of pregelatinized starch 1 part of carbonic acid 65 parts of calcium 10 parts of water
　以上を混合練り押し造粒するした。得られた粒状物を流動層乾燥機で乾燥し、顆粒水和剤を得た。
　次に本発明の有害生物防除剤の奏する効果について、試験例をもって説明する。 The above were mixed, kneaded and pressed and granulated. The obtained granules were dried with a fluid bed dryer to obtain a wettable powder for granules.
Next, the effects of the pest control agent of the present invention will be described with reference to test examples.
［試験例１］コナガ殺虫活性試験
　製剤例２に準じて調製した水和剤を、有効成分として５００ｐｐｍの濃度に水で希釈した。その薬液にキャベツ葉を浸漬し、風乾後、プラスチックカップに入れた。その中にコナガ２齢幼虫１０頭を放ち、蓋をした。その後、２５℃の恒温室に置き、６日後に死虫数を調査し、数１の計算式により死虫率を求めた。試験は1連制で行った。 [Test Example 1] Insecticidal insecticidal activity test A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm as an active ingredient. Cabbage leaves were immersed in the chemical solution, air-dried, and then placed in a plastic cup. 10 second instar larvae of the Japanese moth were released into it and covered. After that, it was placed in a constant temperature room at 25 ° C., and after 6 days, the number of dead insects was examined, and the mortality was calculated by the formula (1). The test was performed in a single system.
Figure JPOXMLDOC01-appb-M000127
Figure JPOXMLDOC01-appb-M000127
　この試験により死虫率９０％以上を示す化合物の化合物番号を以下に挙げる。
　Ａ－００１８、Ａ－００６３、Ａ－００８２、Ａ－０１０４、Ａ－０１０６、Ａ－０１１０、Ａ－０１１３、Ａ－０１１５、Ａ－０１３９、Ａ－０１７６、Ａ－０１８５、Ａ－０３３１、Ａ－０３８６、Ａ－０４３３、Ａ－０５２２、Ａ－０５３９、Ａ－０５７４、Ａ－０６２７、Ａ－０６４８、Ａ－０６５６、Ａ－０６８７、Ａ－０６８９、Ａ－０６９１、Ａ－０７３２、Ａ－０７４５、Ａ－０７５４、Ａ－０７６１、Ａ－０７７３、Ａ－０７７４、Ａ－１０４３、Ａ－２１９６、Ａ－２２８１、Ａ－２２８７、Ａ－２３３１、Ａ－２３３９、Ａ－２３４１、Ａ－２３４５、Ａ－２３４７、Ａ－２３８０、Ａ－２３８１、Ａ－２３８２、Ａ－２３８３、Ａ－２３８４、Ａ－２３９２、Ａ－２４０９、Ａ－２４１０、Ａ－２４１２、Ａ－２４１３、Ａ－２４２０、Ａ－２４５５、Ｂ－０００１、Ｂ－００７７、Ｂ－２２９７、Ｃ－０２４０、Ｄ－２０１１、Ｄ－２０１４、Ｄ－２０１５、Ｄ－２０１６ The compound numbers of compounds showing a mortality of 90% or more by this test are shown below.
A-0018, A-0063, A-0082, A-0104, A-0106, A-0110, A-0113, A-0115, A-0139, A-0176, A-0185, A-0331, A- 0386, A-0433, A-0522, A-0539, A-0574, A-0627, A-0648, A-0656, A-0687, A-0689, A-0691, A-0732, A-0745, A-0754, A-0761, A-0773, A-0774, A-1043, A-2196, A-2281, A-2287, A-2331, A-2339, A-2341, A-2345, A- 2347, A-2380, A-2381, A-2382, A-2383, A-2384, A-2392, A-2409, A-2410, A-2412, A-24 3, A-2420, A-2455, B-0001, B-0077, B-2297, C-0240, D-2011, D-2014, D-2015, D-2016
［試験例２］トビイロウンカ殺虫活性試験
　製剤例２に準じて調製した水和剤を、有効成分として５００ｐｐｍの濃度に水で希釈した。その薬液に、イネの芽出し籾を浸漬し、プラスチックカップに入れた。このプラスチックカップにトビイロウンカ２齢幼虫を１０頭放ち、蓋をした。その後、２５℃の恒温室に置き、６日後に死虫数を調査し、数１の計算式により死虫率を求めた。試験は1連制で行った。 [Test Example 2] Test for insecticidal activity of brown planthoppers The wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm as an active ingredient. Rice sprouting paddy was immersed in the chemical solution and placed in a plastic cup. Ten plastic brown planthopper second-instar larvae were released into the plastic cup, and the lid was closed. After that, it was placed in a constant temperature room at 25 ° C., and after 6 days, the number of dead insects was examined, and the mortality was calculated by the formula (1). The test was performed in a single system.
　比較化合物として、国際公開第２０１７／０１２９７０号記載の化合物番号３５を用いて、上記と同様の試験を行った。比較化合物の構造は以下の通りである。 試 験 The same test as described above was performed using Compound No. 35 described in International Publication WO2017 / 012970 as a comparative compound. The structure of the comparative compound is as follows.
Figure JPOXMLDOC01-appb-C000128
Figure JPOXMLDOC01-appb-C000128
　この試験により死虫率９０％以上を示す化合物の化合物番号を以下に挙げる。
　Ａ－０００１、Ａ－０００２、Ａ－００６６、Ａ－００７５、Ａ－００７７、Ａ－００７９、Ａ－００８２、Ａ－００９６、Ａ－０１０２、Ａ－０１１０、Ａ－０１１２、Ａ－０１１４、Ａ－０１２１、Ａ－０１２４、Ａ－０１６６、Ａ－０１７６、Ａ－０１９１、Ａ－０１９２、Ａ－０２３０、Ａ－０２３２、Ａ－０２４３、Ａ－０２４４、Ａ－０２５２、Ａ－０２５４、Ａ－０２６１、Ａ－０２６３、Ａ－０３３４、Ａ－０３３５、Ａ－０３４０、Ａ－０３４５、Ａ－０３４６、Ａ－０３８１、Ａ－０３８２、Ａ－０３９３、Ａ－０３９４、Ａ－０３９９、Ａ－０４３２、Ａ－０４３４、Ａ－０４４０、Ａ－０４４３、Ａ－０４４５、Ａ－０４７５、Ａ－０４７６、Ａ－０５２１、Ａ－０５２４、Ａ－０５２９、Ａ－０５３２、Ａ－０５３３、Ａ－０５３８、Ａ－０５７１、Ａ－０５７３、Ａ－０５７４、Ａ－０５８１、Ａ－０５８６、Ａ－０６１７、Ａ－０６４１、Ａ－０６４５、Ａ－０６４７、Ａ－０６４８、Ａ－０６５４、Ａ－０６５５、Ａ－０６５６、Ａ－０６５７、Ａ－０６５８、Ａ－０６５９、Ａ－０６６１、Ａ－０６６９、Ａ－０６７４、Ａ－０６８５、Ａ－０７２８、Ａ－０７３４、Ａ－０７４５、Ａ－０７５４、Ａ－０７５６、Ａ－０７６０、Ａ－０７６６、Ａ－０７６７、Ａ－１０１４、Ａ－１０２０、Ａ－１０２１、Ａ－１０２３、Ａ－１０２４、Ａ－１０２５、Ａ－１０４３、Ａ－１０４４、Ａ－１０４５、Ａ－１０４６、Ａ－１０９６、Ａ－２０１７、Ａ－２０２０、Ａ－２０５６、Ａ－２０５９、Ａ－２１１４、Ａ－２１１７、Ａ－２１４０、Ａ－２１７０、Ａ－２１８４、Ａ－２１９７、Ａ－２２１８、Ａ－２２４０、Ａ－２２４３、Ａ－２２４６、Ａ－２２８１、Ａ－２２８９、Ａ－２３１５、Ａ－２３１６、Ａ－２３７３、Ａ－２３７８、Ａ－２３８２、Ａ－２３８４、Ａ－２３８５、Ａ－２３８６、Ａ－２３９２、Ａ－２４１４、Ａ－２４１５、Ａ－２４５３、Ｂ－０００１、Ｂ－０２５７、Ｂ－２００３、Ｃ－０１１１、Ｃ－０１８４、Ｃ－０２３８、Ｃ－０２４０、Ｃ－２３４４、Ｄ－１００４、Ｄ－１００５、Ｄ－２００１、Ｄ－２００２、Ｄ－２００３、Ｄ－２００４、Ｄ－２０１１、Ｄ－２０１６、Ｄ－２０１７、Ｄ－２０２２、Ｄ－２０２３ The compound numbers of compounds showing a mortality of 90% or more by this test are shown below.
A-0001, A-0002, A-0066, A-0075, A-0077, A-0079, A-0082, A-0096, A-0102, A-0110, A-0112, A-0114, A- 0121, A-0124, A-0166, A-0176, A-0191, A-0192, A-0230, A-0232, A-0243, A-0244, A-0252, A-0254, A-0261, A-0263, A-0334, A-0335, A-0340, A-0345, A-0346, A-0381, A-0382, A-0393, A-0394, A-0399, A-0432, A- 0434, A-0440, A-0443, A-0445, A-0475, A-0476, A-0521, A-0524, A-0529, A-0532, A-05 3, A-0538, A-0571, A-0573, A-0574, A-0581, A-0586, A-0617, A-0641, A-0645, A-0647, A-0648, A-0654, A-0655, A-0656, A-0657, A-0658, A-0659, A-0661, A-0669, A-0674, A-0685, A-0728, A0734, A-0745, A- 0754, A-0756, A-0760, A-0766, A-0767, A-1014, A-1020, A-1021, A-1023, A-1024, A-1025, A-1043, A-1044, A-1045, A-1046, A-1096, A-2017, A-2020, A-2056, A-2059, A-2114, A-2117, A-2140, A 2170, A-2184, A-2197, A-2218, A-2240, A-2243, A-2246, A-2281, A-2289, A-2315, A-2316, A-2373, A-2378, A-2382, A-2384, A-2385, A-2386, A-2392, A-2414, A-2415, A-2453, B-0001, B-0257, B-2003, C-0111, C- 0184, C-0238, C-0240, C-2344, D-1004, D-1005, D-2001, D-2002, D-2003, D-2004, D-2011, D-2016, D-2017, D-2022, D-2023
　一方、比較化合物の３５（国際公開第２０１７／０１２９７０号記載）は、５００ｐｐｍの濃度で活性を示さなかった。 On the other hand, 35 of the comparative compound (described in WO 2017/012970) showed no activity at a concentration of 500 ppm.
［試験例３］ナミハダニ防除効果試験
　製剤例２に準じて調製した水和剤を、有効成分として５００ｐｐｍの濃度に水で希釈した。その薬液に、予めナミハダニ雌成虫を３５頭接種しておいたダイズ苗を浸漬し、風乾した。処理後のダイズ苗は２５℃の恒温室に置き、１３日後に雌成虫の生存虫数を調査し、数２の計算式により防除価を求めた。試験は1連制で行った。 [Test Example 3] Test for controlling effects of spider mites A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm as an active ingredient. Soybean seedlings inoculated with 35 adult female spider mites were soaked in the chemical solution and air-dried. The soybean seedlings after the treatment were placed in a constant temperature room at 25 ° C., and after 13 days, the number of surviving female adult insects was examined, and the control value was calculated according to the equation (2). The test was performed in a single system.
Figure JPOXMLDOC01-appb-M000129
Figure JPOXMLDOC01-appb-M000129
　比較化合物として、国際公開第２０１７／０１２９７０号記載の化合物番号３５を用いて、上記と同様の試験を行った。 試 験 The same test as described above was performed using Compound No. 35 described in International Publication WO2017 / 012970 as a comparative compound.
　この試験により防除価９０以上を示す化合物の化合物番号を以下に挙げる。
　Ａ－０００１、Ａ－００１４、Ａ－００１６、Ａ－００２９、Ａ－００６２、Ａ－００６３、Ａ－００６６、Ａ－００７５、Ａ－００７７、Ａ－００７９、Ａ－００８２、Ａ－００９５、Ａ－００９６、Ａ－００９７、Ａ－０１００、Ａ－０１０１、Ａ－０１０２、Ａ－０１０４、Ａ－０１０５、Ａ－０１０７、Ａ－０１０８、Ａ－０１１０、Ａ－０１１３、Ａ－０１２１、Ａ－０１２３、Ａ－０１２４、Ａ－０１２７、Ａ－０１３５、Ａ－０１３９、Ａ－０１５７、Ａ－０１７８、Ａ－０１８０、Ａ－０１８５、Ａ－０１８９、Ａ－０１９０、Ａ－０１９１、Ａ－０１９２、Ａ－０１９５、Ａ－０２００、Ａ－０２１０、Ａ－０２１１、Ａ－０２１２、Ａ－０２１３、Ａ－０２１４、Ａ－０２１６、Ａ－０２３１、Ａ－０２３２、Ａ－０２４２、Ａ－０２４３、Ａ－０２４４、Ａ－０２５２、Ａ－０２５４、Ａ－０２５５、Ａ－０２５７、Ａ－０２６０、Ａ－０２６１、Ａ－０２６２、Ａ－０３３２、Ａ－０３３４、Ａ－０３３５、Ａ－０３４０、Ａ－０３４１、Ａ－０３４６、Ａ－０３８１、Ａ－０３８２、Ａ－０３８３、Ａ－０３８４、Ａ－０３８５、Ａ－０３８６、Ａ－０３８７、Ａ－０３８８、Ａ－０３９３、Ａ－０３９４、Ａ－０３９８、Ａ－０３９９、Ａ－０４００、Ａ－０４３２、Ａ－０４３３、Ａ－０４４０、Ａ－０４４３、Ａ－０４４５、Ａ－０４７２、Ａ－０４７３、Ａ－０４７４、Ａ－０４７５、Ａ－０４７６、Ａ－０４８１、Ａ－０４８５、Ａ－０５２１、Ａ－０５２２、Ａ－０５２３、Ａ－０５２４、Ａ－０５２９、Ａ－０５３０、Ａ－０５３１、Ａ－０５３２、Ａ－０５３７、Ａ－０５３８、Ａ－０５７１、Ａ－０５７２、Ａ－０５７３、Ａ－０５８１、Ａ－０５８２、Ａ－０５８３、Ａ－０５８６、Ａ－０６１８、Ａ－０６２０、Ａ－０６２６、Ａ－０６２７、Ａ－０６３５、Ａ－０６４０、Ａ－０６４１、Ａ－０６４５、Ａ－０６４６、Ａ－０６５０、Ａ－０６５４、Ａ－０６５５、Ａ－０６５６、Ａ－０６５７、Ａ－０６５８、Ａ－０６５９、Ａ－０６６１、Ａ－０６６２、Ａ－０６６３、Ａ－０６６５、Ａ－０６８４、Ａ－０６８６、Ａ－０６９７、Ａ－０７２７、Ａ－０７２８、Ａ－０７３２、Ａ－０７３４、Ａ－０７３９、Ａ－０７４５、Ａ－０７５４、Ａ－０７５６、Ａ－０７６３、Ａ－０７６４、Ａ－０７６６、Ａ－０７６７、Ａ－０７６９、Ａ－０７７０、Ａ－０７７２、Ａ－０７７３、Ａ－０７７４、Ａ－０７７５、Ａ－０７７７、Ａ－０７８２、Ａ－０７８３、Ａ－１００７、Ａ－１００９、Ａ－１０１４、Ａ－１０２０、Ａ－１０２１、Ａ－１０２２、Ａ－１０２３、Ａ－１０２４、Ａ－１０２５、Ａ－１０３３、Ａ－１０４３、Ａ－１０４４、Ａ－１０４５、Ａ－１０４６、Ａ－１０９５、Ａ－１０９６、Ａ－２００３、Ａ－２００６、Ａ－２００９、Ａ－２０１７、Ａ－２０１８、Ａ－２０１９、Ａ－２０２０、Ａ－２０３２、Ａ－２０５５、Ａ－２０５７、Ａ－２０５９、Ａ－２１１４、Ａ－２１１７、Ａ－２１４０、Ａ－２１６９、Ａ－２１７０、Ａ－２１８３、Ａ－２１９７、Ａ－２２１８、Ａ－２２３９、Ａ－２２４０、Ａ－２２４３、Ａ－２２４６、Ａ－２２６１、Ａ－２２７４、Ａ－２２９４、Ａ－２２９５、Ａ－２３０３、Ａ－２３１５、Ａ－２３１６、Ａ－２３１８、Ａ－２３２４、Ａ－２３３１、Ａ－２３４５、Ａ－２３５２、Ａ－２３７３、Ａ－２３８０、Ａ－２３８１、Ａ－２３８３、Ａ－２３８５、Ａ－２３８６、Ａ－２３９２、Ａ－２３９５、Ａ－２３９６、Ａ－２３９７、Ａ－２４１０、Ａ－２４１４、Ａ－２４１６、Ａ－２４１７、Ａ－２４５３、Ａ－２４５５、Ａ－２４５７、Ａ－２４６０、Ｃ－０１１１、Ｄ－２０１３ The compound numbers of the compounds showing a control value of 90 or more by this test are shown below.
A-0001, A-0014, A-0016, A-0029, A-0062, A-0063, A-0066, A-0075, A-0077, A-0079, A-0082, A-0095, A- 0096, A-0097, A-0100, A-0101, A-0102, A-0104, A-0105, A-0107, A-0108, A-0110, A-0113, A-0121, A-0123, A-0124, A-0127, A-0135, A-0139, A-0157, A-0178, A-0180, A-0185, A-0189, A-0190, A-0191, A-0192, A- 0195, A-0200, A-0210, A-0211, A-0212, A-0213, A-0214, A-0216, A-0231, A-0232, A-02 2, A-0243, A-0244, A-0252, A-0254, A-0255, A-0257, A-0260, A-0261, A-0262, A-0332, A-0334, A-0335, A-0340, A-0341, A-0346, A-0381, A-0382, A-0383, A-0384, A-0385, A-0386, A-0387, A-0388, A-0393, A- 0394, A-0398, A-0399, A-0400, A-0432, A-0433, A-0440, A-0443, A-0445, A-0472, A-0473, A-0474, A-0475, A-0476, A-0481, A-0485, A-0521, A-0522, A-0523, A-0524, A-0529, A-0530, A-0531, A 0532, A-0537, A-0538, A-0571, A-0572, A-0573, A-0581, A-0582, A-0583, A-0586, A-0618, A-0620, A-0626, A-0627, A-0635, A-0640, A-0641, A-0645, A-0646, A-0650, A-0654, A-0655, A-0656, A-0657, A-0658, A- 0659, A-0661, A-0662, A-0663, A-0665, A-0684, A-0686, A-0697, A-0727, A-0728, A-0732, A0734, A0739, A-0745, A-0754, A-0756, A-0763, A-0764, A-0766, A-0767, A-0769, A-0770, A-0772 , A-0773, A-0774, A-0775, A-0777, A-0782, A-0783, A-1007, A-1009, A-1014, A-1020, A-1021, A-1022, A -1023, A-1024, A-1025, A-1033, A-1043, A-1044, A-1045, A-1046, A-1095, A-1096, A-2003, A-2006, A-2009 , A-2017, A-2018, A-2019, A-2020, A-2032, A-2055, A-2057, A-2059, A-2114, A-2117, A-2140, A-2169, A -2170, A-2183, A-2197, A-2218, A-2239, A-2240, A-2243, A-2246, A-2261, A-2274, A-2 94, A-2295, A-2303, A-2315, A-2316, A-2318, A-2324, A-2331, A-2345, A-2352, A-2373, A-2380, A-2381, A-2383, A-2385, A-2386, A-2392, A-2395, A-2396, A-2397, A-2410, A-2414, A-2416, A-2417, A-2453, A- 2455, A-2457, A-2460, C-0111, D-2013
　一方、比較化合物の３５（国際公開第２０１７／０１２９７０号記載）は、５００ｐｐｍの濃度で活性を示さなかった。 On the other hand, 35 of the comparative compound (described in WO 2017/012970) showed no activity at a concentration of 500 ppm.
［試験例４］サツマイモネコブセンチュウ制線虫活性試験
　供試化合物をｔｗｅｅｎ２０を１％含有するＮ，Ｎ－ジメチルホルムアミドに溶解し、この溶液を有効成分として２０ｐｐｍの濃度に水で希釈した。その薬液０.５ｍｌと、サツマイモネコブセンチュウ第二期幼虫約３０頭を含む懸濁液０.５ｍｌを混合して有効成分として１０ｐｐｍの濃度とし、２５℃の恒温室に置いた。５日後に顕微鏡下で生存線虫数を数え、数３の計算式により制線虫活性を求めた。試験は２連制で行なった。 [Test Example 4] Test for controlling nematode activity of root-knot nematode of sweet potato The test compound was dissolved in N, N-dimethylformamide containing 1% of tween 20, and this solution was diluted with water to a concentration of 20 ppm as an active ingredient. 0.5 ml of the drug solution and 0.5 ml of a suspension containing about 30 second stage larvae of the root-knot nematode were mixed to give a concentration of 10 ppm as an active ingredient, and placed in a thermostatic chamber at 25 ° C. Five days later, the number of surviving nematodes was counted under a microscope, and the control activity of the nematodes was calculated by the formula of Equation 3. The test was performed in a two-part system.
Figure JPOXMLDOC01-appb-M000130
Figure JPOXMLDOC01-appb-M000130
　比較化合物として、国際公開第２０１７／０１２９７０号記載の化合物番号３５を用いて、上記と同様の試験を行った。 試 験 The same test as described above was performed using Compound No. 35 described in International Publication WO2017 / 012970 as a comparative compound.
　この試験により制線虫率９０％以上を示す化合物の化合物番号を以下に挙げる。
　Ａ－０００１、Ａ－００１４、Ａ－００１６、Ａ－００２４、Ａ－００２５、Ａ－００２９、Ａ－００４８、Ａ－００４９、Ａ－００５２、Ａ－００６２、Ａ－００６３、Ａ－００６６、Ａ－００７５、Ａ－００７６、Ａ－００７７、Ａ－００７９、Ａ－００８２、Ａ－００９５、Ａ－０１０１、Ａ－０１０２、Ａ－０１０４、Ａ－０１０５、Ａ－０１０８、Ａ－０１０９、Ａ－０１１０、Ａ－０１１３、Ａ－０１２１、Ａ－０１２２、Ａ－０１２３、Ａ－０１２４、Ａ－０１３５、Ａ－０１３９、Ａ－０１６１、Ａ－０１６５、Ａ－０１７８、Ａ－０１８４、Ａ－０１８５、Ａ－０１８９、Ａ－０１９０、Ａ－０１９１、Ａ－０１９５、Ａ－０１９７、Ａ－０２００、Ａ－０２１０、Ａ－０２１２、Ａ－０２１６、Ａ－０２２７、Ａ－０２３０、Ａ－０２４２、Ａ－０２４３、Ａ－０２４４、Ａ－０２５２、Ａ－０２５４、Ａ－０２５５、Ａ－０２５７、Ａ－０２６１、Ａ－０３３２、Ａ－０３３５、Ａ－０３４０、Ａ－０３８１、Ａ－０３８２、Ａ－０３８７、Ａ－０３９３、Ａ－０３９４、Ａ－０３９９、Ａ－０４３２、Ａ－０４３３、Ａ－０４４０、Ａ－０４４３、Ａ－０４７６、Ａ－０４８１、Ａ－０５２１、Ａ－０５２２、Ａ－０５２３、Ａ－０５２９、Ａ－０５３０、Ａ－０５３１、Ａ－０５３２、Ａ－０５３８、Ａ－０５７１、Ａ－０５７３、Ａ－０５８１、Ａ－０５８２、Ａ－０５８６、Ａ－０６２０、Ａ－０６３４、Ａ－０６４０、Ａ－０６４１、Ａ－０６４５、Ａ－０６４６、Ａ－０６４９、Ａ－０６５０、Ａ－０６５５、Ａ－０６５６、Ａ－０６５７、Ａ－０６５８、Ａ－０６５９、Ａ－０６６３、Ａ－０６６５、Ａ－０６８３、Ａ－０６８５、Ａ－０６９７、Ａ－０７２７、Ａ－０７２８、Ａ－０７３４、Ａ－０７４５、Ａ－０７５４、Ａ－０７５６、Ａ－０７６２、Ａ－０７６３、Ａ－０７６４、Ａ－０７６６、Ａ－０７６７、Ａ－０７６９、Ａ－０７７３、Ａ－１０１４、Ａ－１０２０、Ａ－１０２１、Ａ－１０２２、Ａ－１０２３、Ａ－１０２４、Ａ－１０２５、Ａ－１０３３、Ａ－１０４３、Ａ－１０４５、Ａ－１０４６、Ａ－１０７８、Ａ－１０８３、Ａ－１０９５、Ａ－１０９６、Ａ－２００３、Ａ－２００６、Ａ－２０１８、Ａ－２０１９、Ａ－２０２０、Ａ－２０５５、Ａ－２０５６、Ａ－２０５７、Ａ－２０５８、Ａ－２０６５、Ａ－２１１４、Ａ－２１１７、Ａ－２１４０、Ａ－２１６７、Ａ－２１６９、Ａ－２１７０、Ａ－２１７３、Ａ－２１８３、Ａ－２１８４、Ａ－２１９５、Ａ－２１９６、Ａ－２１９７、Ａ－２２１８、Ａ－２２２８、Ａ－２２３９、Ａ－２２４０、Ａ－２２４３、Ａ－２２４４、Ａ－２２４６、Ａ－２２６１、Ａ－２２６４、Ａ－２２７５、Ａ－２２８１、Ａ－２２８６、Ａ－２２８７、Ａ－２２９１、Ａ－２２９４、Ａ－２２９５、Ａ－２３１５、Ａ－２３１６、Ａ－２３２５、Ａ－２３３１、Ａ－２３３７、Ａ－２３３９、Ａ－２３４０、Ａ－２３４３、Ａ－２３４５、Ａ－２３４６、Ａ－２３４７、Ａ－２３４８、Ａ－２３５２、Ａ－２３７２、Ａ－２３７３、Ａ－２３７４、Ａ－２３７８、Ａ－２３７９、Ａ－２３８０、Ａ－２３８１、Ａ－２３８３、Ａ－２３９２、Ａ－２３９５、Ａ－２３９６、Ａ－２３９７、Ａ－２４０９、Ａ－２４１０、Ａ－２４１１、Ａ－２４１２、Ａ－２４１３、Ａ－２４１４、Ａ－２４１５、Ａ－２４１６、Ａ－２４１７、Ａ－２４１９、Ａ－２４２０、Ａ－２４５３、Ａ－２４５５、Ａ－２４５７、Ａ－２４６０ The compound numbers of compounds exhibiting a nematode rate of 90% or more by this test are listed below.
A-0001, A-0014, A-0016, A-0024, A-0025, A-0029, A-0048, A-0049, A-0052, A-0062, A-0063, A-0066, A- 0075, A-0076, A-0077, A-0079, A-0082, A-0095, A-0101, A-0102, A-0104, A-0105, A-0108, A-0109, A-0110, A-0113, A-0121, A-0122, A-0123, A-0124, A-0135, A-0139, A-0161, A-0165, A-0178, A-0184, A-0185, A- 0189, A-0190, A-0191, A-0195, A-0197, A-0200, A-0210, A-0212, A-0216, A-0227, A-02 0, A-0242, A-0243, A-0244, A-0252, A-0254, A-0255, A-0257, A-0261, A-0332, A-0335, A-0340, A-0381, A-0382, A-0387, A-0393, A-0394, A-0399, A-0432, A-0433, A-0440, A-0443, A-0476, A-0481, A-0521, A- 0522, A-0523, A-0529, A-0530, A-0531, A-0532, A-0538, A-0571, A-0573, A-0581, A-0582, A-0586, A-0620, A-0634, A-0640, A-0641, A-0645, A-0646, A-0649, A-0650, A-0655, A-0656, A-0657, A 0658, A-0659, A-0663, A-0665, A-0683, A-0685, A-0697, A-0727, A-0728, A0734, A-0745, A-0754, A-0756, A-0762, A-0763, A-0764, A-0766, A-0767, A-0769, A-0773, A-1014, A-1020, A-1021, A-1022, A-1023, A- 1024, A-1025, A-1033, A-1043, A-1045, A-1046, A-1078, A-1083, A-1095, A-1096, A-2003, A-2006, A-2018, A-2019, A-2020, A-2055, A-2056, A-2057, A-2058, A-2065, A-2114, A-2117, A-2140 , A-2167, A-2169, A-2170, A-2173, A-2183, A-2184, A-2195, A-2196, A-2197, A-2218, A-2228, A-2239, A -2240, A-2243, A-2244, A-2246, A-2261, A-2264, A-2275, A-2281, A-2286, A-2287, A-2291, A-2294, A-2295 , A-2315, A-2316, A-2325, A-2331, A-2337, A-2339, A-2340, A-2343, A-2345, A-2346, A-2347, A-2348, A -2352, A-2372, A-2373, A-2374, A-2378, A-2379, A-2380, A-2381, A-2383, A-2392, A-2 95, A-2396, A-2397, A-2409, A-2410, A-2411, A-2412, A-2413, A-2414, A-2415, A-2416, A-2417, A-2419, A-2420, A-2453, A-2455, A-2457, A-2460
　一方、比較化合物の３５（国際公開第２０１７／０１２９７０号記載）は、１０ｐｐｍの濃度で活性を示さなかった。 On the other hand, 35 of the comparative compound (described in WO2017 / 012970) showed no activity at a concentration of 10 ppm.
　本発明の一般式［Ｉ］で表される化合物又はその塩は優れた有害生物防除作用を有し、農薬や殺虫剤などの有効成分として有用である。また、本発明の一般式［ＩＩ］で表される化合物及び本発明の一般式［ＩＩＩ］で表される化合物は一般式［Ｉ］で表される化合物の製造中間体として有用である。本発明はこれらの分野等で産業上の利用可能性を有している。 The compound of the present invention represented by the general formula [I] or a salt thereof has an excellent pest control effect and is useful as an active ingredient such as an agricultural chemical or an insecticide. Further, the compound represented by the general formula [II] of the present invention and the compound represented by the general formula [III] of the present invention are useful as intermediates for producing the compound represented by the general formula [I]. The present invention has industrial applicability in these fields and the like.

Claims (14)

  1. 一般式［Ｉ］
    Figure JPOXMLDOC01-appb-C000001
     　[式中、
    　Ｒ１は、水素原子、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｒ８によって任意に置換されたＣ３～Ｃ６シクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、－ＮＨ２、－Ｎ（Ｒ９）Ｒ１０、－ＯＨ、－ＯＲ１１、－Ｓ（＝Ｏ）２Ｒ１１、－ＣＨ＝ＮＯＲ１１又は飽和複素環を示し、
    　Ｒ２は、水素原子、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、－Ｓ（＝Ｏ）２Ｒ１１、－Ｃ（＝Ｏ）Ｒ１１、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１１を示すか、或いは、Ｒ１及びＲ２は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく
    　Ａは、酸素原子又は硫黄原子を示し、
    　Ｒ３は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、－ＮＨ２、－Ｎ（Ｒ９）Ｒ１０、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｓ）ＮＨ２を示し、
    　ｎは、０～３の整数を示し、
    　Ｒ４は、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、－ＮＨ２又は－Ｎ（Ｒ９）Ｒ１０を示し、
    　Ｒ５は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｒ８によって任意に置換されたＣ３～Ｃ６シクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｒ１３によって任意に置換されたＣ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｒ１３によって任意に置換されたＣ２～Ｃ６アルキニル基、－ＯＨ、－ＯＣ（＝Ｏ）Ｒ１４、－ＯＳ（＝Ｏ）２Ｒ１４、－ＯＳｉ（Ｒ１４）２Ｒ１２、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルコキシ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルコキシ基、Ｃ２～Ｃ６アルケニルオキシ基、Ｃ２～Ｃ６ハロアルケニルオキシ基、Ｃ２～Ｃ６アルキニルオキシ基、Ｃ２～Ｃ６ハロアルキニルオキシ基、Ｃ３～Ｃ６シクロアルキルオキシ基、Ｃ３～Ｃ６ハロシクロアルキルオキシ基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルオキシ基、芳香族複素環オキシ基、飽和複素環オキシ基、－ＳＨ、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルチオ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルスルフィニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルスルホニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルチオ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルスルフィニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルスルホニル基、Ｃ２～Ｃ６アルケニルチオ基、Ｃ２～Ｃ６アルケニルスルフィニル基、Ｃ２～Ｃ６アルケニルスルホニル基、Ｃ２～Ｃ６ハロアルケニルチオ基、Ｃ２～Ｃ６ハロアルケニルスルフィニル基、Ｃ２～Ｃ６ハロアルケニルスルホニル基、Ｃ２～Ｃ６アルキニルチオ基、Ｃ２～Ｃ６アルキニルスルフィニル基、Ｃ２～Ｃ６アルキニルスルホニル基、Ｃ３～Ｃ６シクロアルキルチオ基、Ｃ３～Ｃ６シクロアルキルスルフィニル基、Ｃ３～Ｃ６シクロアルキルスルホニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルチオ基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルスルフィニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルスルホニル基、芳香族複素環チオ基、芳香族複素環スルフィニル基、芳香族複素環スルホニル基、飽和複素環チオ基、飽和複素環スルフィニル基、飽和複素環スルホニル基、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１４、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｃ（Ｒ１５）＝ＮＯＨ又は－Ｃ（Ｒ１５）＝ＮＯＲ１４を示し、
    　Ｒ６は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルコキシ基、Ｃ２～Ｃ６アルケニルオキシ基、Ｃ２～Ｃ６ハロアルケニルオキシ基、Ｃ２～Ｃ６アルキニルオキシ基、Ｃ２～Ｃ６ハロアルキニルオキシ基、Ｃ３～Ｃ６シクロアルキルオキシ基、Ｃ３～Ｃ６ハロシクロアルキルオキシ基、－ＳＨ、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、Ｃ２～Ｃ６アルケニルチオ基、Ｃ２～Ｃ６アルケニルスルフィニル基、Ｃ２～Ｃ６アルケニルスルホニル基、Ｃ２～Ｃ６アルキニルチオ基、Ｃ２～Ｃ６アルキニルスルフィニル基、Ｃ２～Ｃ６アルキニルスルホニル基、Ｃ３～Ｃ６シクロアルキルチオ基、Ｃ３～Ｃ６シクロアルキルスルフィニル基、Ｃ３～Ｃ６シクロアルキルスルホニル基、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｎ＝Ｃ（Ｒ１２）Ｒ１４、－Ｎ＝Ｃ（Ｒ１５）Ｎ（Ｒ１２）Ｒ１４、－ＮＨＣ（Ｒ１５）＝ＮＯＲ１４、－Ｎ＝Ｓ（Ｒ１４）Ｒ１２、－Ｎ＝Ｓ（＝Ｏ）（Ｒ１４）Ｒ１２、－Ｎ（Ｒ１０）ＮＨ２、－Ｎ（Ｒ１０）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（Ｒ１５）＝ＮＯＨ、－Ｃ（Ｒ１５）＝ＮＯＲ１４、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１４、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
    　Ｒ７は、シアノ基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
    　Ｒ８は、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
    　Ｒ９は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ３～Ｃ６シクロアルキル基、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１１、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１又は－Ｓ（＝Ｏ）２Ｒ１１を示し、
    　Ｒ１０は、水素原子、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ３～Ｃ６シクロアルキル基、－Ｃ（＝Ｏ）Ｒ１１、－Ｃ（＝Ｏ）ＯＲ１１又は－Ｓ（＝Ｏ）２Ｒ１１を示すか、或いは、Ｒ９及びＲ１０は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
    　Ｒ１１は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示し、
    　Ｒ１２は、水素原子、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示すか、或いは、Ｒ１１及びＲ１２は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
    　Ｒ１３は、シアノ基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－ＯＨ、－ＯＲ１４、－ＯＣ（＝Ｏ）Ｒ１４、－ＯＳ（＝Ｏ）２Ｒ１４、－ＯＳｉ（Ｒ１４）２Ｒ１２、－ＳＨ、－ＳＲ１４、－Ｓ（＝Ｏ）Ｒ１４、－Ｓ（＝Ｏ）２Ｒ１４、－Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１４、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｓ）ＮＨ２、－Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（Ｒ１５）＝ＮＯＨ、－Ｃ（Ｒ１５）＝ＮＯＲ１４、－Ｓｉ（Ｒ１４）２Ｒ１２、無置換若しくは（Ｚ）ｐ１により置換されたフェニル基、芳香族複素環又は飽和複素環を示し、
    　Ｒ１４は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルＣ１～Ｃ６アルキル基、芳香族複素環、芳香族複素環Ｃ１～Ｃ６アルキル基、飽和複素環又は飽和複素環Ｃ１～Ｃ６アルキル基を示すか、或いは、Ｒ１２及びＲ１４は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
    　Ｒ１５は、水素原子、ハロゲン原子、－ＮＨ２、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示すか、或いは、Ｒ１４及びＲ１５は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
    　Ｚは、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、－ＮＨ２、モノ（Ｃ１～Ｃ６アルキル）アミノ基、ジ（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルキルカルボニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルキルカルボニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルコキシカルボニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルコキシカルボニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルキルスルホニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルキルスルホニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６ハロアルキルスルホニルアミノ基、Ｎ－（Ｃ１～Ｃ６ハロアルキルスルホニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、－Ｃ（＝Ｏ）ＮＨ２、モノ（Ｃ１～Ｃ６アルキル）アミノカルボニル基、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル基、モノ（Ｃ１～Ｃ６ハロアルキル）アミノカルボニル基又はフェニル基を示し、
    　芳香族複素環は、
    Figure JPOXMLDOC01-appb-C000002
     　飽和複素環は、
    Figure JPOXMLDOC01-appb-C000003
     を示し、
    　ｐ１は、０～５の整数を示し、
    　ｐ２は、０～４の整数を示し、
    　ｐ３は、０～３の整数を示し、
    　ｐ４は、０～２の整数を示し、
    　ｔは、０又は１の整数を示す］
    で表されることを特徴とする３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩。     General formula [I]
    Figure JPOXMLDOC01-appb-C000001
     [Where,
    R 1 is a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkyl group optionally substituted by R 7 , a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, C 3 -C 6 cycloalkyl group optionally substituted by R 8 , C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl group, C 2 -C 6 alkynyl group, A C 2 -C 6 haloalkynyl group, —NH 2 , —N (R 9 ) R 10 , —OH, —OR 11 , —S (＝ O) 2 R 11 , —CH ＝ NOR 11 or a saturated heterocyclic ring ,
    R 2 is a hydrogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkyl group optionally substituted by R 7 , a C 3 -C 6 cycloalkyl group , A C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, —S (＝ O) 2 R 11 , —C (＝ O) R 11 , —C (＝ O) OR 11 , —C (＝ O ) NH 2 , —C (＝ O) N (R 12 ) R 11 or —C (＝ O) N (R 12 ) OR 11 , or R 1 and R 2 are bonded to each other to form C A 2 to C 6 alkylene bond may be formed, wherein the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom, and the C 2 -C 6 alkylene bond may be a halogen atom or C 1 -C 6 may be mono- or poly-substituted by an alkyl group. A child or a sulfur atom;
    R 3 is a halogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylthio group, a C 1 -C 6 alkylsulfinyl group , C 1 -C 6 alkylsulfonyl group, —NH 2 , —N (R 9 ) R 10 , —C (＝ O) NH 2 or —C (＝ S) NH 2 ,
    n represents an integer of 0 to 3,
    R 4 is a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano group, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl Groups, C 2 -C 6 alkynyl groups, C 2 -C 6 haloalkynyl groups, —OH, C 1 -C 6 alkoxy groups, C 1 -C 6 haloalkoxy groups, C 1 -C 6 alkylthio groups, C 1- C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group, —NH 2 or —N (R 9 ) R 10 ,
    R 5 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, C 1 ~ C 6 alkyl group, C 1 ~ C 6 haloalkyl group, C 1 ~ C 6 alkyl group optionally substituted by R 13, R 13 C 1 ~ C 6 haloalkyl group optionally substituted by, C 3 ~ C 6 cycloalkyl group, C 3 ~ C 6 halocycloalkyl group, C 3 ~ C 6 cycloalkyl group optionally substituted by R 8, C 2 ~ C 6 alkenyl group, C 2 ~ C 6 haloalkenyl group, C 2 ~ C 6 alkenyl group optionally substituted by R 13, C 2 ~ C 6 alkynyl group, C 2 ~ C 6 haloalkynyl group, A C 2 -C 6 alkynyl group optionally substituted with R 13 , —OH, —OC (＝ O) R 14 , —OS (＝ O) 2 R 14 , —OSi (R 14 ) 2 R 12 , C 1 ~ C Alkoxy group, C 1 ~ C 6 haloalkoxy group, C 1 ~ C 6 alkoxy group optionally substituted by R 13, C 1 ~ C 6 haloalkoxy group optionally substituted by R 13, C 2 ~ C 6 Alkenyloxy group, C 2 -C 6 haloalkenyloxy group, C 2 -C 6 alkynyloxy group, C 2 -C 6 haloalkynyloxy group, C 3 -C 6 cycloalkyloxy group, C 3 -C 6 halocyclo Alkyloxy group, unsubstituted or substituted by (Z) p 1 phenyloxy group, aromatic heterocyclic oxy group, saturated heterocyclic oxy group, —SH, C 1 -C 6 alkylthio group, C 1 -C 6 alkyl sulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 B alkylsulfonyl group, C 1 ~ C 6 alkylthio group optionally substituted by R 13, C which is optionally substituted by R 13 1 ~ C 6 alkylsulfinyl group, C 1 ~ C which is optionally substituted by R 13 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group optionally substituted by R 13, C 1 ~ C 6 haloalkylsulfenyl optionally substituted by R 13 sulfinyl group, C 1 ~ optionally substituted by R 13 C 6 haloalkylsulfonyl group, C 2 ~ C 6 alkenylthio group, C 2 ~ C 6 alkenylsulfinyl group, C 2 ~ C 6 alkenyl sulfonyl group, C 2 ~ C 6 haloalkenyl two thio group, C 2 ~ C 6 haloalkenyl A sulfinyl group, a C 2 -C 6 haloalkenylsulfonyl group, a C 2 -C 6 alkynylthio group, C 2 ~ C 6 alkynylsulfinyl group, C 2 ~ C 6 alkynyl-sulfonyl group, C 3 ~ C 6 cycloalkylthio group, C 3 ~ C 6 cycloalkyl alkylsulfinyl group, C 3 ~ C 6 cycloalkyl alkylsulfonyl group, an unsubstituted or (Z) phenylthio group substituted by p 1, an unsubstituted or (Z) phenyl sulfinyl group substituted by p 1, an unsubstituted or (Z) phenylsulfonyl group substituted by p 1, an aromatic heterocyclic thio group An aromatic heterocyclic sulfinyl group, an aromatic heterocyclic sulfonyl group, a saturated heterocyclic thio group, a saturated heterocyclic sulfinyl group, a saturated heterocyclic sulfonyl group, -NH 2 , -N (R 12 ) R 14 , -N (R 10) C (= O) H , -N (R 10) C (= O) R 14, -N (R 10) C (= O) OR 14, -N (R 10 C (= O) NH 2, -N (R 10) C (= O) N (R 12) R 14, -N (R 10) C (= O) N (R 12) OR 14, -N (R 10 ) C (= S) NH 2 , -N (R 10 ) C (= S) N (R 12 ) R 14 , -N (R 10 ) S (= O) 2 R 14 , -N (R 10 ) S (= O) 2 NH 2 , -N (R 10) S (= O) 2 N (R 12) R 14, -C (= O) H, -C (= O) R 14, -C (= O) OH, —C (（O) OR 14 , —C (＝ O) NH 2 , —C (＝ O) N (R 12 ) R 14 , —C (＝ O) N (R 12 ) OR 14 , -C (R 15 ) = NOH or -C (R 15 ) = NOR 14 ,
    R 6 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkyl group optionally substituted with R 7 , C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl group, C 2 -C 6 alkynyl group, C 2 -C 6 haloalkynyl group , -OH, C 1 ~ C 6 alkoxy group, C 1 ~ C 6 haloalkoxy group, C 1 ~ C 6 alkoxy group optionally substituted by R 7, C 2 ~ C 6 alkenyloxy group, C 2 ~ C 6 haloalkenyloxy group, C 2 ~ C 6 alkynyloxy group, C 2 ~ C 6 haloalkynyl group, C 3 ~ C 6 cycloalkyl group, C 3 ~ C 6 halocycloalkyl group, - H, C 1 ~ C 6 alkylthio group, C 1 ~ C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl, C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, C 2 -C 6 alkenylsulfonyl, C 2 -C 6 alkynylthio, C 2 -C 6 alkynylsulfinyl, C 2 ~ C 6 alkynylsulfonyl group, C 3 ~ C 6 cycloalkylthio group, C 3 ~ C 6 cycloalkyl alkylsulfinyl group, C 3 ~ C 6 cycloalkyl sulfonyl group, -NH 2, -N (R 12 ) R 14 , -N (R 10) C ( = O) H, -N (R 10) C (= O) R 14, -N (R 10) C (= O) OR 14, -N (R 10) C (= O) NH 2, -N (R 10) C (= O) N (R 12) R 14, -N (R 10) C (= O) N (R 12 ) OR 14 , —N (R 10 ) C (= S) NH 2 , —N (R 10 ) C (= S) N (R 12 ) R 14 , —N (R 10 ) S (= O) 2 R 14, -N (R 10) S (= O) 2 NH 2, -N (R 10) S (= O) 2 N (R 12) R 14, -N = C (R 12) R 14, -N = C (R 15 ) N (R 12 ) R 14 , -NHC (R 15 ) = NOR 14 , -N = S (R 14 ) R 12 , -N = S (= O) (R 14 ) R 12 , —N (R 10 ) NH 2 , —N (R 10 ) N (R 12 ) R 14 , —N (R 10 ) N (R 10 ) C (（O) H, —N (R 10 ) N (R 10 ) C (= O) R 14, -N (R 10) N (R 10) C (= O) OR 14, -N (R 10) N (R 10) S (= O) 2 R 14, -C (= O) H, - C (= O) R 14 , -C (R 15 ) = NOH, -C (R 15 ) = NOR 14 , -C (= O) OH, -C (= O) OR 14 , -C (= O) NH 2 or —C (＝ O) N (R 12 ) R 11
    R 7 is a cyano group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —OH, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylthio group, a C 1 -C 6 Alkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, —C (＝ O) OH, —C (＝ O) OR 11 , —C (＝ O) NH 2 or —C (＝ O) N (R 12 ) R 11 represents
    R 8 is a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —C (＝ O) OR 11 indicates -C (= O) NH 2 or -C (= O) N (R 12) R 11,
    R 9 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 3 -C 6 cycloalkyl group, a —C (＝ O ) H, -C (= O) R 11 , -C (= O) OR 11 , -C (= O) NH 2 , -C (= O) N (R 12 ) R 11 or -S (= O) 2 R 11 ;
    R 10 is a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 3 -C 6 cycloalkyl group, a —C (＝ O) R 11 , —C (＝ O) OR 11 or —S (＝ O) 2 R 11 , or R 9 and R 10 are mutually bonded to form a C 2 -C 6 alkylene bond Wherein the alkylene linkage may contain one oxygen, sulfur or nitrogen atom and the C 2 -C 6 alkylene linkage is monosubstituted by a halogen atom or a C 1 -C 6 alkyl group. Or may be poly-substituted,
    R 11 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano C A 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or A C 3 -C 6 halocycloalkyl group;
    R 12 is a hydrogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group , A C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group, or R 11 and R 12 are bonded to each other to form a C 2 -C 6 A 6 alkylene bond may be formed, wherein the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom, and the C 2 -C 6 alkylene bond is a halogen atom or a C 1 -C 6 alkyl group. May be mono-substituted or poly-substituted,
    R 13 is a cyano group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —OH, —OR 14 , —OC (＝ O) R 14 , —OS (＝ O) 2 R 14, -OSi (R 14) 2 R 12, -SH, -SR 14, -S (= O) R 14, -S (= O) 2 R 14, -S (= O) 2 N (R 12) R 14 , —NH 2 , —N (R 12 ) R 14 , —N (R 10 ) C (＝ O) H, —N (R 10 ) C (＝ O) R 14 , —N (R 10 ) C (= O) OR 14 , -N (R 10 ) C (= O) NH 2 , -N (R 10 ) C (= O) N (R 12 ) R 14 , -N (R 10 ) C (= O ) N (R 12 ) OR 14 , —N (R 10 ) C (= S) NH 2 , —N (R 10 ) C (= S) N (R 12 ) R 14 , —N (R 10 ) S ( = O) 2 R 14, -N ( R 10) S (= O) 2 NH 2, -N (R 10) S (= O) 2 N (R 12) R 14, -C (= O) H, - C (= O) R 14 , -C (= O) OH, -C (= O) OR 14 , -C (= O) NH 2 , -C (= O) N (R 12 ) R 14 , -C (= S) NH 2 , —C (＝ S) N (R 12 ) R 14 , —C (R 15 ) = NOH, —C (R 15 ) = NOR 14 , —Si (R 14 ) 2 R 12 , A phenyl group, an aromatic heterocyclic ring or a saturated heterocyclic ring, which is unsubstituted or substituted by (Z) p 1 ,
    R 14 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano C A 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, unsubstituted or substituted with (Z) p 1 phenyl group, unsubstituted or substituted with (Z) p 1 phenyl C 1 -C 6 alkyl group, aromatic heterocyclic ring Represents an aromatic heterocyclic C 1 -C 6 alkyl group, a saturated heterocyclic ring or a saturated heterocyclic C 1 -C 6 alkyl group, or R 12 and R 14 are mutually bonded to form C 2 -C 6 Alkylene bond May form, this time the alkylene bonded oxygen atom, may contain one sulfur atom or a nitrogen atom, and C 2 ~ C 6 alkylene linkage monosubstituted or by halogen atoms or C 1 ~ C 6 alkyl group May be poly-substituted,
    R 15 represents a hydrogen atom, a halogen atom, —NH 2 , a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, Represents a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group, or R 14 and R 15 are each other May combine to form a C 2 -C 6 alkylene bond, wherein the alkylene bond may contain one oxygen, sulfur or nitrogen atom, and the C 2 -C 6 alkylene bond may be a halogen atom or May be mono- or poly-substituted by a C 1 -C 6 alkyl group,
    Z is a halogen atom, cyano group, nitro group, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, —OH, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1 ~ C 6 alkylthio group, C 1 ~ C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group , —NH 2 , mono (C 1 -C 6 alkyl) amino group, di (C 1 -C 6 alkyl) amino group, C 1 -C 6 alkylcarbonylamino group, N- (C 1 -C 6 alkylcarbonyl) -N- (C 1 -C 6 alkyl) amino group, C 1 -C 6 alkoxycarbonylamino group, N- (C 1 -C 6 alkoxycarbonyl) -N- (C 1 -C 6- alkyl) amino group, C 1 -C 6 alkylsulfonylamino group, N- (C 1 -C 6 alkylsulfonyl) -N- (C 1 -C 6 alkyl) amino group, C 1 -C 6 haloalkylsulfonylamino group , N- (C 1 -C 6 haloalkylsulfonyl) -N- (C 1 -C 6 alkyl) amino group, —C (＝ O) NH 2 , mono (C 1 -C 6 alkyl) aminocarbonyl group, di ( A C 1 -C 6 alkyl) aminocarbonyl group, a mono (C 1 -C 6 haloalkyl) aminocarbonyl group or a phenyl group;
    An aromatic heterocycle is
    Figure JPOXMLDOC01-appb-C000002
     A saturated heterocycle is
    Figure JPOXMLDOC01-appb-C000003
     Indicates that
    p 1 represents an integer of 0 to 5,
    p 2 represents an integer of 0 to 4,
    p 3 represents an integer of 0 to 3,
    p 4 represents an integer of 0 to 2,
    t represents an integer of 0 or 1]
    A 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or an agriculturally acceptable salt thereof, represented by the formula:
  2. 請求項１に記載の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩を有効成分として含有する農薬組成物。 An agricultural chemical composition comprising the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or the agriculturally acceptable salt thereof according to claim 1 as an active ingredient.
  3. 農薬組成物が、さらに界面活性剤を含有する請求項２に記載の農薬組成物。 The pesticidal composition according to claim 2, wherein the pesticidal composition further contains a surfactant.
  4. 請求項１に記載の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩を活性成分として含有する有害生物防除剤。 A pesticidal composition comprising the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative according to claim 1 or an agriculturally acceptable salt thereof as an active ingredient.
  5. 有害生物防除剤が、殺虫剤、殺センチュウ剤及び殺ダニ剤である請求項４に記載の有害生物防除剤。 The pesticide according to claim 4, wherein the pesticide is an insecticide, a nematicide, and a miticide.
  6. 農園芸用植物を栽培する畑地又は水田における有害生物に対して、防除効力を有する請求項５に記載の有害生物防除剤。 The pest control agent according to claim 5, which has a controlling effect on pests in a field or a paddy field where agricultural and horticultural plants are cultivated.
  7. 農園芸用植物が、育種法又は遺伝子組換え技術により耐性を付与された植物である請求項６に記載の有害生物防除剤。 The pesticidal composition according to claim 6, wherein the agricultural and horticultural plant is a plant to which resistance has been imparted by a breeding method or a genetic recombination technique.
  8. 請求項１に記載の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩の有効成分量を使用する有害生物の防除方法。 A method for controlling pests using the active ingredient of the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or the agriculturally acceptable salt thereof according to claim 1.
  9. 請求項１に記載の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩を有効成分として含有する農薬組成物を、農園芸用作物または農園芸用作物を生育させようとする若しくは生育している場所に対して、同時に又は分割して作用させることによる、有害生物の防除方法。 An agricultural or horticultural crop comprising the pesticidal composition containing the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or the agriculturally acceptable salt thereof according to claim 1 as an active ingredient. A method for controlling pests by simultaneously or separately acting on a place where an agricultural or horticultural crop is to be grown or is growing.
  10. 有害生物防除剤を施用する場所が、水田、畑地、芝地、果樹園、非農耕地、温室、育苗施設、植物工場のいずれかである請求項８又は請求項９に記載の有害生物の防除方法。 The pest control according to claim 8 or 9, wherein the place to which the pesticide is applied is any one of a paddy field, a field, a lawn, an orchard, a non-cultivated land, a greenhouse, a nursery, and a plant factory. Method.
  11. 請求項１に記載の３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸アミド誘導体又はその農業上許容される塩を殺虫剤、殺センチュウ剤及び殺ダニ剤として使用する請求項８～１０のいずれか一項に記載の有害生物の防除方法。 Use of the 3- (1H-1,2,4-triazol-1-yl) benzoic acid amide derivative or the agriculturally acceptable salt thereof according to claim 1 as an insecticide, nematocide and acaricide. Item 11. The method for controlling pests according to any one of Items 8 to 10.
  12. 請求項４～７のいずれか一項に記載の有害生物防除剤を、農園芸用作物に対する有害生物を防除に使用する記載の有害生物防除剤の使用方法。 Use of the pesticidal composition according to any one of claims 4 to 7, wherein the pesticidal composition is used for controlling pests on agricultural and horticultural crops.
  13. 一般式［ＩＩ］
    Figure JPOXMLDOC01-appb-C000004
     　[式中、
    　Ｋは、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、フェニルオキシ基又は無置換若しくは（Ｚ）ｐ１により置換されたフェニルＣ１～Ｃ６アルコキシ基を示し、
    　Ｒ３は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、－ＮＨ２、－Ｎ（Ｒ９）Ｒ１０、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｓ）ＮＨ２を示し、
    　ｎは、０～３の整数を示し、
    　Ｒ４は、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、－ＮＨ２又は－Ｎ（Ｒ９）Ｒ１０を示し、
    　Ｒ５は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｒ８によって任意に置換されたＣ３～Ｃ６シクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｒ１３によって任意に置換されたＣ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｒ１３によって任意に置換されたＣ２～Ｃ６アルキニル基、－ＯＨ、－ＯＳ（＝Ｏ）２Ｒ１４、－ＯＳｉ（Ｒ１４）２Ｒ１２、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルコキシ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルコキシ基、Ｃ２～Ｃ６アルケニルオキシ基、Ｃ２～Ｃ６ハロアルケニルオキシ基、Ｃ２～Ｃ６アルキニルオキシ基、Ｃ２～Ｃ６ハロアルキニルオキシ基、Ｃ３～Ｃ６シクロアルキルオキシ基、Ｃ３～Ｃ６ハロシクロアルキルオキシ基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルオキシ基、芳香族複素環オキシ基、飽和複素環オキシ基、－ＳＨ、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルチオ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルスルフィニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルスルホニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルチオ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルスルフィニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルスルホニル基、Ｃ２～Ｃ６アルケニルチオ基、Ｃ２～Ｃ６アルケニルスルフィニル基、Ｃ２～Ｃ６アルケニルスルホニル基、Ｃ２～Ｃ６ハロアルケニルチオ基、Ｃ２～Ｃ６ハロアルケニルスルフィニル基、Ｃ２～Ｃ６ハロアルケニルスルホニル基、Ｃ２～Ｃ６アルキニルチオ基、Ｃ２～Ｃ６アルキニルスルフィニル基、Ｃ２～Ｃ６アルキニルスルホニル基、Ｃ３～Ｃ６シクロアルキルチオ基、Ｃ３～Ｃ６シクロアルキルスルフィニル基、Ｃ３～Ｃ６シクロアルキルスルホニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルチオ基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルスルフィニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルスルホニル基、芳香族複素環チオ基、芳香族複素環スルフィニル基、芳香族複素環スルホニル基、飽和複素環チオ基、飽和複素環スルフィニル基、飽和複素環スルホニル基、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｃ（Ｒ１５）＝ＮＯＨ又は－Ｃ（Ｒ１５）＝ＮＯＲ１４を示し、
    　Ｒ６は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルコキシ基、Ｃ２～Ｃ６アルケニルオキシ基、Ｃ２～Ｃ６ハロアルケニルオキシ基、Ｃ２～Ｃ６アルキニルオキシ基、Ｃ２～Ｃ６ハロアルキニルオキシ基、Ｃ３～Ｃ６シクロアルキルオキシ基、Ｃ３～Ｃ６ハロシクロアルキルオキシ基、－ＳＨ、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、Ｃ２～Ｃ６アルケニルチオ基、Ｃ２～Ｃ６アルケニルスルフィニル基、Ｃ２～Ｃ６アルケニルスルホニル基、Ｃ２～Ｃ６アルキニルチオ基、Ｃ２～Ｃ６アルキニルスルフィニル基、Ｃ２～Ｃ６アルキニルスルホニル基、Ｃ３～Ｃ６シクロアルキルチオ基、Ｃ３～Ｃ６シクロアルキルスルフィニル基、Ｃ３～Ｃ６シクロアルキルスルホニル基、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｎ＝Ｃ（Ｒ１２）Ｒ１４、－Ｎ＝Ｃ（Ｒ１５）Ｎ（Ｒ１２）Ｒ１４、－ＮＨＣ（Ｒ１５）＝ＮＯＲ１４、－Ｎ＝Ｓ（Ｒ１４）Ｒ１２、－Ｎ＝Ｓ（＝Ｏ）（Ｒ１４）Ｒ１２、－Ｎ（Ｒ１０）ＮＨ２、－Ｎ（Ｒ１０）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（Ｒ１５）＝ＮＯＨ、－Ｃ（Ｒ１５）＝ＮＯＲ１４、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
    　Ｒ７は、シアノ基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
    　Ｒ８は、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
    　Ｒ９は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ３～Ｃ６シクロアルキル基、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１１、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１又は－Ｓ（＝Ｏ）２Ｒ１１を示し、
    　Ｒ１０は、水素原子、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ３～Ｃ６シクロアルキル基、－Ｃ（＝Ｏ）Ｒ１１、－Ｃ（＝Ｏ）ＯＲ１１又は－Ｓ（＝Ｏ）２Ｒ１１を示すか、或いは、Ｒ９及びＲ１０は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
    　Ｒ１１は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示し、
    　Ｒ１２は、水素原子、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示すか、或いは、Ｒ１１及びＲ１２は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
    　Ｒ１３は、シアノ基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－ＯＨ、－ＯＲ１４、－ＯＳ（＝Ｏ）２Ｒ１４、－ＯＳｉ（Ｒ１４）２Ｒ１２、－ＳＨ、－ＳＲ１４、－Ｓ（＝Ｏ）Ｒ１４、－Ｓ（＝Ｏ）２Ｒ１４、－Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｓ）ＮＨ２、－Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（Ｒ１５）＝ＮＯＨ、－Ｃ（Ｒ１５）＝ＮＯＲ１４、－Ｓｉ（Ｒ１４）２Ｒ１２、無置換若しくは（Ｚ）ｐ１により置換されたフェニル基、芳香族複素環又は飽和複素環を示し、
    　Ｒ１４は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルＣ１～Ｃ６アルキル基、芳香族複素環、芳香族複素環Ｃ１～Ｃ６アルキル基、飽和複素環又は飽和複素環Ｃ１～Ｃ６アルキル基を示すか、或いは、Ｒ１２及びＲ１４は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
    　Ｒ１５は、水素原子、ハロゲン原子、－ＮＨ２、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示すか、或いは、Ｒ１４及びＲ１５は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
    　Ｚは、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、－ＮＨ２、モノ（Ｃ１～Ｃ６アルキル）アミノ基、ジ（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルキルカルボニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルキルカルボニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルコキシカルボニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルコキシカルボニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルキルスルホニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルキルスルホニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６ハロアルキルスルホニルアミノ基、Ｎ－（Ｃ１～Ｃ６ハロアルキルスルホニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、－Ｃ（＝Ｏ）ＮＨ２、モノ（Ｃ１～Ｃ６アルキル）アミノカルボニル基、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル基、モノ（Ｃ１～Ｃ６ハロアルキル）アミノカルボニル基又はフェニル基を示し、
    　芳香族複素環は、
    Figure JPOXMLDOC01-appb-C000005
     　飽和複素環は、
    Figure JPOXMLDOC01-appb-C000006
     を示し、
    　ｐ１は、０～５の整数を示し、
    　ｐ２は、０～４の整数を示し、
    　ｐ３は、０～３の整数を示し、
    　ｐ４は、０～２の整数を示し、
    　ｔは、０又は１の整数を示す］
    で表されることを特徴とする３－（１Ｈ－１，２，４－トリアゾール－１－イル）安息香酸誘導体又はその塩。     General formula [II]
    Figure JPOXMLDOC01-appb-C000004
     [Where,
    K represents -OH, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkoxy group, a phenyloxy group or a phenyl C 1 -C 6 alkoxy group which is unsubstituted or substituted by (Z) p 1 ;
    R 3 is a halogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylthio group, a C 1 -C 6 alkylsulfinyl group , C 1 -C 6 alkylsulfonyl group, —NH 2 , —N (R 9 ) R 10 , —C (＝ O) NH 2 or —C (＝ S) NH 2 ,
    n represents an integer of 0 to 3,
    R 4 is a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano group, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl Groups, C 2 -C 6 alkynyl groups, C 2 -C 6 haloalkynyl groups, —OH, C 1 -C 6 alkoxy groups, C 1 -C 6 haloalkoxy groups, C 1 -C 6 alkylthio groups, C 1- C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group, —NH 2 or —N (R 9 ) R 10 ,
    R 5 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, C 1 ~ C 6 alkyl group, C 1 ~ C 6 haloalkyl group, C 1 ~ C 6 alkyl group optionally substituted by R 13, R 13 C 1 ~ C 6 haloalkyl group optionally substituted by, C 3 ~ C 6 cycloalkyl group, C 3 ~ C 6 halocycloalkyl group, C 3 ~ C 6 cycloalkyl group optionally substituted by R 8, C 2 ~ C 6 alkenyl group, C 2 ~ C 6 haloalkenyl group, C 2 ~ C 6 alkenyl group optionally substituted by R 13, C 2 ~ C 6 alkynyl group, C 2 ~ C 6 haloalkynyl group, C 2 ~ C 6 alkynyl group optionally substituted by R 13, -OH, -OS (= O) 2 R 14, -OSi (R 14) 2 R 12, C 1 ~ C 6 alkoxy group, C 1 ~ 6 haloalkoxy group, C 1 ~ C 6 alkoxy group optionally substituted by R 13, C 1 ~ C 6 haloalkoxy group optionally substituted by R 13, C 2 ~ C 6 alkenyloxy group, C 2 ~ C 6 haloalkenyloxy group, C 2 -C 6 alkynyloxy group, C 2 -C 6 haloalkynyloxy group, C 3 -C 6 cycloalkyloxy group, C 3 -C 6 halocycloalkyloxy group, unsubstituted or (Z) phenyloxy group, aromatic heterocyclic oxy group, saturated heterocyclic oxy group, —SH, C 1 -C 6 alkylthio group, C 1 -C 6 alkylsulfinyl group, C 1 -C substituted by p 1 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group C 1 ~ C 6 alkylthio group optionally substituted by R 13, C 1 ~ C 6 alkylsulfinyl optionally substituted by R 13 sulfinyl group, C 1 ~ C 6 alkylsulfonyl group optionally substituted by R 13, C 1 ~ C 6 haloalkylthio group optionally substituted by R 13, C 1 ~ C 6 haloalkylsulfenyl optionally substituted by R 13 sulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group optionally substituted by R 13 , C 2 ~ C 6 alkenylthio group, C 2 ~ C 6 alkenylsulfinyl group, C 2 ~ C 6 alkenyl sulfonyl group, C 2 ~ C 6 haloalkenyl two thio group, C 2 ~ C 6 halo alkenylsulfinyl group, C 2 ~ C 6 haloalkenyl sulfonyl group, C 2 ~ C 6 alkynylthio, C 2 ~ C 6 alkynyl Rufiniru group, C 2 ~ C 6 alkynyl-sulfonyl group, C 3 ~ C 6 cycloalkylthio group, C 3 ~ C 6 cycloalkyl alkylsulfinyl group, C 3 ~ C 6 cycloalkyl sulfonyl group, the unsubstituted or (Z) p 1 Substituted phenylthio group, unsubstituted or substituted by (Z) p 1 phenylsulfinyl group, unsubstituted or substituted by (Z) p 1 phenylsulfonyl group, aromatic heterocyclic thio group, aromatic heterocyclic sulfinyl Group, aromatic heterocyclic sulfonyl group, saturated heterocyclic thio group, saturated heterocyclic sulfinyl group, saturated heterocyclic sulfonyl group, -NH 2 , -N (R 12 ) R 14 , -N (R 10 ) C (= O ) H, -N (R 10) C (= O) R 14, -N (R 10) C (= O) OR 14, -N (R 10) C (= O) NH 2, - (R 10) C (= O ) N (R 12) R 14, -N (R 10) C (= O) N (R 12) OR 14, -N (R 10) C (= S) NH 2, -N (R 10) C (= S) N (R 12) R 14, -N (R 10) S (= O) 2 R 14, -N (R 10) S (= O) 2 NH 2, - N (R 10) S (= O) 2 N (R 12) R 14, -C (= O) H, -C (= O) R 14, -C (= O) NH 2, -C (= O ) N (R 12 ) R 14 , —C (＝ O) N (R 12 ) OR 14 , —C (R 15 ) = NOH or —C (R 15 ) = NOR 14
    R 6 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkyl group optionally substituted with R 7 , C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl group, C 2 -C 6 alkynyl group, C 2 -C 6 haloalkynyl group , -OH, C 1 ~ C 6 alkoxy group, C 1 ~ C 6 haloalkoxy group, C 1 ~ C 6 alkoxy group optionally substituted by R 7, C 2 ~ C 6 alkenyloxy group, C 2 ~ C 6 haloalkenyloxy group, C 2 ~ C 6 alkynyloxy group, C 2 ~ C 6 haloalkynyl group, C 3 ~ C 6 cycloalkyl group, C 3 ~ C 6 halocycloalkyl group, - H, C 1 ~ C 6 alkylthio group, C 1 ~ C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl, C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, C 2 -C 6 alkenylsulfonyl, C 2 -C 6 alkynylthio, C 2 -C 6 alkynylsulfinyl, C 2 ~ C 6 alkynylsulfonyl group, C 3 ~ C 6 cycloalkylthio group, C 3 ~ C 6 cycloalkyl alkylsulfinyl group, C 3 ~ C 6 cycloalkyl sulfonyl group, -NH 2, -N (R 12 ) R 14 , -N (R 10) C ( = O) H, -N (R 10) C (= O) R 14, -N (R 10) C (= O) OR 14, -N (R 10) C (= O) NH 2, -N (R 10) C (= O) N (R 12) R 14, -N (R 10) C (= O) N (R 12 ) OR 14 , —N (R 10 ) C (= S) NH 2 , —N (R 10 ) C (= S) N (R 12 ) R 14 , —N (R 10 ) S (= O) 2 R 14, -N (R 10) S (= O) 2 NH 2, -N (R 10) S (= O) 2 N (R 12) R 14, -N = C (R 12) R 14, -N = C (R 15 ) N (R 12 ) R 14 , -NHC (R 15 ) = NOR 14 , -N = S (R 14 ) R 12 , -N = S (= O) (R 14 ) R 12 , —N (R 10 ) NH 2 , —N (R 10 ) N (R 12 ) R 14 , —N (R 10 ) N (R 10 ) C (（O) H, —N (R 10 ) N (R 10 ) C (= O) R 14, -N (R 10) N (R 10) C (= O) OR 14, -N (R 10) N (R 10) S (= O) 2 R 14, -C (= O) H, - C (＝ O) R 14 , —C (R 15 ) = NOH, —C (R 15 ) = NOR 14 , —C (＝ O) NH 2 or —C (＝ O) N (R 12 ) R 11 Show,
    R 7 is a cyano group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —OH, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylthio group, a C 1 -C 6 An alkylsulfinyl group, a C 1 -C 6 alkylsulfonyl group, —C (＝ O) NH 2 or —C (＝ O) N (R 12 ) R 11 ,
    R 8 is a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —C (＝ O) NH 2 Or —C (＝ O) N (R 12 ) R 11 ;
    R 9 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 3 -C 6 cycloalkyl group, a —C (＝ O ) H, -C (= O) R 11 , -C (= O) OR 11 , -C (= O) NH 2 , -C (= O) N (R 12 ) R 11 or -S (= O) 2 R 11 ;
    R 10 is a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 3 -C 6 cycloalkyl group, a —C (＝ O) R 11 , —C (＝ O) OR 11 or —S (＝ O) 2 R 11 , or R 9 and R 10 are mutually bonded to form a C 2 -C 6 alkylene bond Wherein the alkylene linkage may contain one oxygen, sulfur or nitrogen atom and the C 2 -C 6 alkylene linkage is monosubstituted by a halogen atom or a C 1 -C 6 alkyl group. Or may be poly-substituted,
    R 11 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano C A 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or A C 3 -C 6 halocycloalkyl group;
    R 12 is a hydrogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group , A C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group, or R 11 and R 12 are bonded to each other to form a C 2 -C 6 A 6 alkylene bond may be formed, wherein the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom, and the C 2 -C 6 alkylene bond is a halogen atom or a C 1 -C 6 alkyl group. May be mono-substituted or poly-substituted,
    R 13 is a cyano group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —OH, —OR 14 , —OS (＝ O) 2 R 14 , —OSi (R 14 ) 2 R 12 , -SH, -SR 14 , -S (= O) R 14 , -S (= O) 2 R 14 , -S (= O) 2 N (R 12 ) R 14 , -NH 2 , -N (R 12 ) R 14 , —N (R 10 ) C (＝ O) H, —N (R 10 ) C (＝ O) R 14 , —N (R 10 ) C (＝ O) OR 14 , —N (R 10 ) C (＝ O) NH 2 , —N (R 10 ) C (＝ O) N (R 12 ) R 14 , —N (R 10 ) C (＝ O) N (R 12 ) OR 14 , -N (R 10 ) C (= S) NH 2 , -N (R 10 ) C (= S) N (R 12 ) R 14 , -N (R 10 ) S (= O) 2 R 14 , -N ( 10) S (= O) 2 NH 2, -N (R 10) S (= O) 2 N (R 12) R 14, -C (= O) H, -C (= O) R 14, -C (= O) NH 2 , -C (= O) N (R 12 ) R 14 , -C (= S) NH 2 , -C (= S) N (R 12 ) R 14 , -C (R 15 ) ＮＯNOH, —C (R 15 ) ＮＯNOR 14 , —Si (R 14 ) 2 R 12 , a phenyl group, an aromatic heterocyclic ring or a saturated heterocyclic ring, which is unsubstituted or substituted by (Z) p 1 ,
    R 14 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano C A 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, unsubstituted or substituted with (Z) p 1 phenyl group, unsubstituted or substituted with (Z) p 1 phenyl C 1 -C 6 alkyl group, aromatic heterocyclic ring Represents an aromatic heterocyclic C 1 -C 6 alkyl group, a saturated heterocyclic ring or a saturated heterocyclic C 1 -C 6 alkyl group, or R 12 and R 14 are mutually bonded to form C 2 -C 6 Alkylene bond May form, this time the alkylene bonded oxygen atom, may contain one sulfur atom or a nitrogen atom, and C 2 ~ C 6 alkylene linkage monosubstituted or by halogen atoms or C 1 ~ C 6 alkyl group May be poly-substituted,
    R 15 represents a hydrogen atom, a halogen atom, —NH 2 , a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, Represents a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group, or R 14 and R 15 are each other May combine to form a C 2 -C 6 alkylene bond, wherein the alkylene bond may contain one oxygen, sulfur or nitrogen atom, and the C 2 -C 6 alkylene bond may be a halogen atom or May be mono- or poly-substituted by a C 1 -C 6 alkyl group,
    Z is a halogen atom, cyano group, nitro group, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, —OH, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1 ~ C 6 alkylthio group, C 1 ~ C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group , —NH 2 , mono (C 1 -C 6 alkyl) amino group, di (C 1 -C 6 alkyl) amino group, C 1 -C 6 alkylcarbonylamino group, N- (C 1 -C 6 alkylcarbonyl) -N- (C 1 -C 6 alkyl) amino group, C 1 -C 6 alkoxycarbonylamino group, N- (C 1 -C 6 alkoxycarbonyl) -N- (C 1 -C 6- alkyl) amino group, C 1 -C 6 alkylsulfonylamino group, N- (C 1 -C 6 alkylsulfonyl) -N- (C 1 -C 6 alkyl) amino group, C 1 -C 6 haloalkylsulfonylamino group , N- (C 1 -C 6 haloalkylsulfonyl) -N- (C 1 -C 6 alkyl) amino group, —C (＝ O) NH 2 , mono (C 1 -C 6 alkyl) aminocarbonyl group, di ( A C 1 -C 6 alkyl) aminocarbonyl group, a mono (C 1 -C 6 haloalkyl) aminocarbonyl group or a phenyl group;
    An aromatic heterocycle is
    Figure JPOXMLDOC01-appb-C000005
     A saturated heterocycle is
    Figure JPOXMLDOC01-appb-C000006
     Indicates that
    p 1 represents an integer of 0 to 5,
    p 2 represents an integer of 0 to 4,
    p 3 represents an integer of 0 to 3,
    p 4 represents an integer of 0 to 2,
    t represents an integer of 0 or 1]
    A 3- (1H-1,2,4-triazol-1-yl) benzoic acid derivative or a salt thereof, which is represented by the following formula:
  14. 一般式［ＩＩＩ］
    Figure JPOXMLDOC01-appb-C000007
     　[式中、
    　Ｗは、水素原子、ハロゲン原子又はシアノ基を示し、
    　Ｒ３は、ハロゲン原子、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、－ＮＨ２、－Ｎ（Ｒ９）Ｒ１０、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｓ）ＮＨ２を示し、
    　ｎは、０～３の整数を示し、
    　Ｒ４は、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、－ＮＨ２又は－Ｎ（Ｒ９）Ｒ１０を示し、
    　Ｒ５は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｒ８によって任意に置換されたＣ３～Ｃ６シクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｒ１３によって任意に置換されたＣ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｒ１３によって任意に置換されたＣ２～Ｃ６アルキニル基、－ＯＨ、－ＯＣ（＝Ｏ）Ｒ１４、－ＯＳ（＝Ｏ）２Ｒ１４、－ＯＳｉ（Ｒ１４）２Ｒ１２、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルコキシ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルコキシ基、Ｃ２～Ｃ６アルケニルオキシ基、Ｃ２～Ｃ６ハロアルケニルオキシ基、Ｃ２～Ｃ６アルキニルオキシ基、Ｃ２～Ｃ６ハロアルキニルオキシ基、Ｃ３～Ｃ６シクロアルキルオキシ基、Ｃ３～Ｃ６ハロシクロアルキルオキシ基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルオキシ基、芳香族複素環オキシ基、飽和複素環オキシ基、－ＳＨ、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルチオ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルスルフィニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６アルキルスルホニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルチオ基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルスルフィニル基、Ｒ１３によって任意に置換されたＣ１～Ｃ６ハロアルキルスルホニル基、Ｃ２～Ｃ６アルケニルチオ基、Ｃ２～Ｃ６アルケニルスルフィニル基、Ｃ２～Ｃ６アルケニルスルホニル基、Ｃ２～Ｃ６ハロアルケニルチオ基、Ｃ２～Ｃ６ハロアルケニルスルフィニル基、Ｃ２～Ｃ６ハロアルケニルスルホニル基、Ｃ２～Ｃ６アルキニルチオ基、Ｃ２～Ｃ６アルキニルスルフィニル基、Ｃ２～Ｃ６アルキニルスルホニル基、Ｃ３～Ｃ６シクロアルキルチオ基、Ｃ３～Ｃ６シクロアルキルスルフィニル基、Ｃ３～Ｃ６シクロアルキルスルホニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルチオ基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルスルフィニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルスルホニル基、芳香族複素環チオ基、芳香族複素環スルフィニル基、芳香族複素環スルホニル基、飽和複素環チオ基、飽和複素環スルフィニル基、飽和複素環スルホニル基、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１４、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｃ（Ｒ１５）＝ＮＯＨ又は－Ｃ（Ｒ１５）＝ＮＯＲ１４を示し、
    　Ｒ６は、水素原子、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｒ７によって任意に置換されたＣ１～Ｃ６アルコキシ基、Ｃ２～Ｃ６アルケニルオキシ基、Ｃ２～Ｃ６ハロアルケニルオキシ基、Ｃ２～Ｃ６アルキニルオキシ基、Ｃ２～Ｃ６ハロアルキニルオキシ基、Ｃ３～Ｃ６シクロアルキルオキシ基、Ｃ３～Ｃ６ハロシクロアルキルオキシ基、－ＳＨ、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、Ｃ２～Ｃ６アルケニルチオ基、Ｃ２～Ｃ６アルケニルスルフィニル基、Ｃ２～Ｃ６アルケニルスルホニル基、Ｃ２～Ｃ６アルキニルチオ基、Ｃ２～Ｃ６アルキニルスルフィニル基、Ｃ２～Ｃ６アルキニルスルホニル基、Ｃ３～Ｃ６シクロアルキルチオ基、Ｃ３～Ｃ６シクロアルキルスルフィニル基、Ｃ３～Ｃ６シクロアルキルスルホニル基、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｎ＝Ｃ（Ｒ１２）Ｒ１４、－Ｎ＝Ｃ（Ｒ１５）Ｎ（Ｒ１２）Ｒ１４、－ＮＨＣ（Ｒ１５）＝ＮＯＲ１４、－Ｎ＝Ｓ（Ｒ１４）Ｒ１２、－Ｎ＝Ｓ（＝Ｏ）（Ｒ１４）Ｒ１２、－Ｎ（Ｒ１０）ＮＨ２、－Ｎ（Ｒ１０）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（Ｒ１５）＝ＮＯＨ、－Ｃ（Ｒ１５）＝ＮＯＲ１４、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１４、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
    　Ｒ７は、シアノ基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
    　Ｒ８は、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２又は－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１を示し、
    　Ｒ９は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ３～Ｃ６シクロアルキル基、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１１、－Ｃ（＝Ｏ）ＯＲ１１、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１１又は－Ｓ（＝Ｏ）２Ｒ１１を示し、
    　Ｒ１０は、水素原子、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ３～Ｃ６シクロアルキル基、－Ｃ（＝Ｏ）Ｒ１１、－Ｃ（＝Ｏ）ＯＲ１１又は－Ｓ（＝Ｏ）２Ｒ１１を示すか、或いは、Ｒ９及びＲ１０は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
    　Ｒ１１は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示し、
    　Ｒ１２は、水素原子、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示すか、或いは、Ｒ１１及びＲ１２は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
    　Ｒ１３は、シアノ基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、－ＯＨ、－ＯＲ１４、－ＯＣ（＝Ｏ）Ｒ１４、－ＯＳ（＝Ｏ）２Ｒ１４、－ＯＳｉ（Ｒ１４）２Ｒ１２、－ＳＨ、－ＳＲ１４、－Ｓ（＝Ｏ）Ｒ１４、－Ｓ（＝Ｏ）２Ｒ１４、－Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－ＮＨ２、－Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｈ、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｏ）Ｎ（Ｒ１２）ＯＲ１４、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）ＮＨ２、－Ｎ（Ｒ１０）Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｒ１４、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２ＮＨ２、－Ｎ（Ｒ１０）Ｓ（＝Ｏ）２Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｏ）Ｈ、－Ｃ（＝Ｏ）Ｒ１４、－Ｃ（＝Ｏ）ＯＨ、－Ｃ（＝Ｏ）ＯＲ１４、－Ｃ（＝Ｏ）ＮＨ２、－Ｃ（＝Ｏ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（＝Ｓ）ＮＨ２、－Ｃ（＝Ｓ）Ｎ（Ｒ１２）Ｒ１４、－Ｃ（Ｒ１５）＝ＮＯＨ、－Ｃ（Ｒ１５）＝ＮＯＲ１４、－Ｓｉ（Ｒ１４）２Ｒ１２、無置換若しくは（Ｚ）ｐ１により置換されたフェニル基、芳香族複素環又は飽和複素環を示し、
    　Ｒ１４は、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ１～Ｃ６アルコキシＣ１～Ｃ６アルキル基、Ｃ１～Ｃ６アルキルチオＣ１～Ｃ６アルキル基、シアノＣ１～Ｃ６アルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基、Ｃ３～Ｃ６ハロシクロアルキル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニル基、無置換若しくは（Ｚ）ｐ１により置換されたフェニルＣ１～Ｃ６アルキル基、芳香族複素環、芳香族複素環Ｃ１～Ｃ６アルキル基、飽和複素環又は飽和複素環Ｃ１～Ｃ６アルキル基を示すか、或いは、Ｒ１２及びＲ１４は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
    　Ｒ１５は、水素原子、ハロゲン原子、－ＮＨ２、シアノ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、Ｃ２～Ｃ６アルケニル基、Ｃ２～Ｃ６ハロアルケニル基、Ｃ２～Ｃ６アルキニル基、Ｃ２～Ｃ６ハロアルキニル基、Ｃ３～Ｃ６シクロアルキル基又はＣ３～Ｃ６ハロシクロアルキル基を示すか、或いは、Ｒ１４及びＲ１５は、相互に結合してＣ２～Ｃ６アルキレン結合を形成してもよく、このときこのアルキレン結合は酸素原子、硫黄原子又は窒素原子を１個含んでもよく、且つＣ２～Ｃ６アルキレン結合はハロゲン原子又はＣ１～Ｃ６アルキル基によりモノ置換又はポリ置換されてもよく、
    　Ｚは、ハロゲン原子、シアノ基、ニトロ基、Ｃ１～Ｃ６アルキル基、Ｃ１～Ｃ６ハロアルキル基、－ＯＨ、Ｃ１～Ｃ６アルコキシ基、Ｃ１～Ｃ６ハロアルコキシ基、Ｃ１～Ｃ６アルキルチオ基、Ｃ１～Ｃ６アルキルスルフィニル基、Ｃ１～Ｃ６アルキルスルホニル基、Ｃ１～Ｃ６ハロアルキルチオ基、Ｃ１～Ｃ６ハロアルキルスルフィニル基、Ｃ１～Ｃ６ハロアルキルスルホニル基、－ＮＨ２、モノ（Ｃ１～Ｃ６アルキル）アミノ基、ジ（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルキルカルボニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルキルカルボニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルコキシカルボニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルコキシカルボニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６アルキルスルホニルアミノ基、Ｎ－（Ｃ１～Ｃ６アルキルスルホニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、Ｃ１～Ｃ６ハロアルキルスルホニルアミノ基、Ｎ－（Ｃ１～Ｃ６ハロアルキルスルホニル）－Ｎ－（Ｃ１～Ｃ６アルキル）アミノ基、－Ｃ（＝Ｏ）ＮＨ２、モノ（Ｃ１～Ｃ６アルキル）アミノカルボニル基、ジ（Ｃ１～Ｃ６アルキル）アミノカルボニル基、モノ（Ｃ１～Ｃ６ハロアルキル）アミノカルボニル基又はフェニル基を示し、
    　芳香族複素環は、
    Figure JPOXMLDOC01-appb-C000008
     　飽和複素環は、
    Figure JPOXMLDOC01-appb-C000009
     を示し、
    　ｐ１は、０～５の整数を示し、
    　ｐ２は、０～４の整数を示し、
    　ｐ３は、０～３の整数を示し、
    　ｐ４は、０～２の整数を示し、
    　ｔは、０又は１の整数を示す］
    で表されることを特徴とする１－フェニル－１Ｈ－１，２，４－トリアゾール誘導体又はその塩。     General formula [III]
    Figure JPOXMLDOC01-appb-C000007
     [Where,
    W represents a hydrogen atom, a halogen atom or a cyano group,
    R 3 is a halogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylthio group, a C 1 -C 6 alkylsulfinyl group , C 1 -C 6 alkylsulfonyl group, —NH 2 , —N (R 9 ) R 10 , —C (＝ O) NH 2 or —C (＝ S) NH 2 ,
    n represents an integer of 0 to 3,
    R 4 is a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano group, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl Groups, C 2 -C 6 alkynyl groups, C 2 -C 6 haloalkynyl groups, —OH, C 1 -C 6 alkoxy groups, C 1 -C 6 haloalkoxy groups, C 1 -C 6 alkylthio groups, C 1- C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group, —NH 2 or —N (R 9 ) R 10 ,
    R 5 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, C 1 ~ C 6 alkyl group, C 1 ~ C 6 haloalkyl group, C 1 ~ C 6 alkyl group optionally substituted by R 13, R 13 C 1 ~ C 6 haloalkyl group optionally substituted by, C 3 ~ C 6 cycloalkyl group, C 3 ~ C 6 halocycloalkyl group, C 3 ~ C 6 cycloalkyl group optionally substituted by R 8, C 2 ~ C 6 alkenyl group, C 2 ~ C 6 haloalkenyl group, C 2 ~ C 6 alkenyl group optionally substituted by R 13, C 2 ~ C 6 alkynyl group, C 2 ~ C 6 haloalkynyl group, A C 2 -C 6 alkynyl group optionally substituted with R 13 , —OH, —OC (＝ O) R 14 , —OS (＝ O) 2 R 14 , —OSi (R 14 ) 2 R 12 , C 1 ~ C Alkoxy group, C 1 ~ C 6 haloalkoxy group, C 1 ~ C 6 alkoxy group optionally substituted by R 13, C 1 ~ C 6 haloalkoxy group optionally substituted by R 13, C 2 ~ C 6 Alkenyloxy group, C 2 -C 6 haloalkenyloxy group, C 2 -C 6 alkynyloxy group, C 2 -C 6 haloalkynyloxy group, C 3 -C 6 cycloalkyloxy group, C 3 -C 6 halocyclo Alkyloxy group, unsubstituted or substituted by (Z) p 1 phenyloxy group, aromatic heterocyclic oxy group, saturated heterocyclic oxy group, —SH, C 1 -C 6 alkylthio group, C 1 -C 6 alkyl sulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 B alkylsulfonyl group, C 1 ~ C 6 alkylthio group optionally substituted by R 13, C which is optionally substituted by R 13 1 ~ C 6 alkylsulfinyl group, C 1 ~ C which is optionally substituted by R 13 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group optionally substituted by R 13, C 1 ~ C 6 haloalkylsulfenyl optionally substituted by R 13 sulfinyl group, C 1 ~ optionally substituted by R 13 C 6 haloalkylsulfonyl group, C 2 ~ C 6 alkenylthio group, C 2 ~ C 6 alkenylsulfinyl group, C 2 ~ C 6 alkenyl sulfonyl group, C 2 ~ C 6 haloalkenyl two thio group, C 2 ~ C 6 haloalkenyl A sulfinyl group, a C 2 -C 6 haloalkenylsulfonyl group, a C 2 -C 6 alkynylthio group, C 2 ~ C 6 alkynylsulfinyl group, C 2 ~ C 6 alkynyl-sulfonyl group, C 3 ~ C 6 cycloalkylthio group, C 3 ~ C 6 cycloalkyl alkylsulfinyl group, C 3 ~ C 6 cycloalkyl alkylsulfonyl group, an unsubstituted or (Z) phenylthio group substituted by p 1, an unsubstituted or (Z) phenyl sulfinyl group substituted by p 1, an unsubstituted or (Z) phenylsulfonyl group substituted by p 1, an aromatic heterocyclic thio group An aromatic heterocyclic sulfinyl group, an aromatic heterocyclic sulfonyl group, a saturated heterocyclic thio group, a saturated heterocyclic sulfinyl group, a saturated heterocyclic sulfonyl group, -NH 2 , -N (R 12 ) R 14 , -N (R 10) C (= O) H , -N (R 10) C (= O) R 14, -N (R 10) C (= O) OR 14, -N (R 10 C (= O) NH 2, -N (R 10) C (= O) N (R 12) R 14, -N (R 10) C (= O) N (R 12) OR 14, -N (R 10 ) C (= S) NH 2 , -N (R 10 ) C (= S) N (R 12 ) R 14 , -N (R 10 ) S (= O) 2 R 14 , -N (R 10 ) S (= O) 2 NH 2 , -N (R 10) S (= O) 2 N (R 12) R 14, -C (= O) H, -C (= O) R 14, -C (= O) OH, —C (（O) OR 14 , —C (＝ O) NH 2 , —C (＝ O) N (R 12 ) R 14 , —C (＝ O) N (R 12 ) OR 14 , -C (R 15 ) = NOH or -C (R 15 ) = NOR 14 ,
    R 6 is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkyl group optionally substituted with R 7 , C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl group, C 2 -C 6 alkynyl group, C 2 -C 6 haloalkynyl group , -OH, C 1 ~ C 6 alkoxy group, C 1 ~ C 6 haloalkoxy group, C 1 ~ C 6 alkoxy group optionally substituted by R 7, C 2 ~ C 6 alkenyloxy group, C 2 ~ C 6 haloalkenyloxy group, C 2 ~ C 6 alkynyloxy group, C 2 ~ C 6 haloalkynyl group, C 3 ~ C 6 cycloalkyl group, C 3 ~ C 6 halocycloalkyl group, - H, C 1 ~ C 6 alkylthio group, C 1 ~ C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl, C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, C 2 -C 6 alkenylsulfonyl, C 2 -C 6 alkynylthio, C 2 -C 6 alkynylsulfinyl, C 2 ~ C 6 alkynylsulfonyl group, C 3 ~ C 6 cycloalkylthio group, C 3 ~ C 6 cycloalkyl alkylsulfinyl group, C 3 ~ C 6 cycloalkyl sulfonyl group, -NH 2, -N (R 12 ) R 14 , -N (R 10) C ( = O) H, -N (R 10) C (= O) R 14, -N (R 10) C (= O) OR 14, -N (R 10) C (= O) NH 2, -N (R 10) C (= O) N (R 12) R 14, -N (R 10) C (= O) N (R 12 ) OR 14 , —N (R 10 ) C (= S) NH 2 , —N (R 10 ) C (= S) N (R 12 ) R 14 , —N (R 10 ) S (= O) 2 R 14, -N (R 10) S (= O) 2 NH 2, -N (R 10) S (= O) 2 N (R 12) R 14, -N = C (R 12) R 14, -N = C (R 15 ) N (R 12 ) R 14 , -NHC (R 15 ) = NOR 14 , -N = S (R 14 ) R 12 , -N = S (= O) (R 14 ) R 12 , —N (R 10 ) NH 2 , —N (R 10 ) N (R 12 ) R 14 , —N (R 10 ) N (R 10 ) C (（O) H, —N (R 10 ) N (R 10 ) C (= O) R 14, -N (R 10) N (R 10) C (= O) OR 14, -N (R 10) N (R 10) S (= O) 2 R 14, -C (= O) H, - C (= O) R 14 , -C (R 15 ) = NOH, -C (R 15 ) = NOR 14 , -C (= O) OH, -C (= O) OR 14 , -C (= O) NH 2 or —C (＝ O) N (R 12 ) R 11
    R 7 is a cyano group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —OH, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkylthio group, a C 1 -C 6 Alkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, —C (＝ O) OH, —C (＝ O) OR 11 , —C (＝ O) NH 2 or —C (＝ O) N (R 12 ) R 11 represents
    R 8 is a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —C (＝ O) OR 11 indicates -C (= O) NH 2 or -C (= O) N (R 12) R 11,
    R 9 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 3 -C 6 cycloalkyl group, a —C (＝ O ) H, -C (= O) R 11 , -C (= O) OR 11 , -C (= O) NH 2 , -C (= O) N (R 12 ) R 11 or -S (= O) 2 R 11 ;
    R 10 is a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 3 -C 6 cycloalkyl group, a —C (＝ O) R 11 , —C (＝ O) OR 11 or —S (＝ O) 2 R 11 , or R 9 and R 10 are mutually bonded to form a C 2 -C 6 alkylene bond Wherein the alkylene linkage may contain one oxygen, sulfur or nitrogen atom and the C 2 -C 6 alkylene linkage is monosubstituted by a halogen atom or a C 1 -C 6 alkyl group. Or may be poly-substituted,
    R 11 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano C A 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or A C 3 -C 6 halocycloalkyl group;
    R 12 is a hydrogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group , A C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group, or R 11 and R 12 are bonded to each other to form a C 2 -C 6 A 6 alkylene bond may be formed, wherein the alkylene bond may contain one oxygen atom, sulfur atom or nitrogen atom, and the C 2 -C 6 alkylene bond is a halogen atom or a C 1 -C 6 alkyl group. May be mono-substituted or poly-substituted,
    R 13 is a cyano group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 halocycloalkyl group, —OH, —OR 14 , —OC (＝ O) R 14 , —OS (＝ O) 2 R 14, -OSi (R 14) 2 R 12, -SH, -SR 14, -S (= O) R 14, -S (= O) 2 R 14, -S (= O) 2 N (R 12) R 14 , —NH 2 , —N (R 12 ) R 14 , —N (R 10 ) C (＝ O) H, —N (R 10 ) C (＝ O) R 14 , —N (R 10 ) C (= O) OR 14 , -N (R 10 ) C (= O) NH 2 , -N (R 10 ) C (= O) N (R 12 ) R 14 , -N (R 10 ) C (= O ) N (R 12 ) OR 14 , —N (R 10 ) C (= S) NH 2 , —N (R 10 ) C (= S) N (R 12 ) R 14 , —N (R 10 ) S ( = O) 2 R 14, -N ( R 10) S (= O) 2 NH 2, -N (R 10) S (= O) 2 N (R 12) R 14, -C (= O) H, - C (= O) R 14 , -C (= O) OH, -C (= O) OR 14 , -C (= O) NH 2 , -C (= O) N (R 12 ) R 14 , -C (= S) NH 2 , —C (＝ S) N (R 12 ) R 14 , —C (R 15 ) = NOH, —C (R 15 ) = NOR 14 , —Si (R 14 ) 2 R 12 , A phenyl group, an aromatic heterocyclic ring or a saturated heterocyclic ring, which is unsubstituted or substituted by (Z) p 1 ,
    R 14 is a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 1 -C 6 alkoxy C 1 -C 6 alkyl group, a C 1 -C 6 alkylthio C 1 -C 6 alkyl group, a cyano C A 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group, C 3 -C 6 halocycloalkyl group, unsubstituted or substituted with (Z) p 1 phenyl group, unsubstituted or substituted with (Z) p 1 phenyl C 1 -C 6 alkyl group, aromatic heterocyclic ring Represents an aromatic heterocyclic C 1 -C 6 alkyl group, a saturated heterocyclic ring or a saturated heterocyclic C 1 -C 6 alkyl group, or R 12 and R 14 are mutually bonded to form C 2 -C 6 Alkylene bond May form, this time the alkylene bonded oxygen atom, may contain one sulfur atom or a nitrogen atom, and C 2 ~ C 6 alkylene linkage monosubstituted or by halogen atoms or C 1 ~ C 6 alkyl group May be poly-substituted,
    R 15 represents a hydrogen atom, a halogen atom, —NH 2 , a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 haloalkenyl group, Represents a C 2 -C 6 alkynyl group, a C 2 -C 6 haloalkynyl group, a C 3 -C 6 cycloalkyl group or a C 3 -C 6 halocycloalkyl group, or R 14 and R 15 are each other May combine to form a C 2 -C 6 alkylene bond, wherein the alkylene bond may contain one oxygen, sulfur or nitrogen atom, and the C 2 -C 6 alkylene bond may be a halogen atom or May be mono- or poly-substituted by a C 1 -C 6 alkyl group,
    Z is a halogen atom, cyano group, nitro group, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, —OH, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1 ~ C 6 alkylthio group, C 1 ~ C 6 alkylsulfinyl group, C 1 ~ C 6 alkylsulfonyl group, C 1 ~ C 6 haloalkylthio group, C 1 ~ C 6 haloalkylsulfinyl group, C 1 ~ C 6 haloalkylsulfonyl group , —NH 2 , mono (C 1 -C 6 alkyl) amino group, di (C 1 -C 6 alkyl) amino group, C 1 -C 6 alkylcarbonylamino group, N- (C 1 -C 6 alkylcarbonyl) -N- (C 1 -C 6 alkyl) amino group, C 1 -C 6 alkoxycarbonylamino group, N- (C 1 -C 6 alkoxycarbonyl) -N- (C 1 -C 6- alkyl) amino group, C 1 -C 6 alkylsulfonylamino group, N- (C 1 -C 6 alkylsulfonyl) -N- (C 1 -C 6 alkyl) amino group, C 1 -C 6 haloalkylsulfonylamino group , N- (C 1 -C 6 haloalkylsulfonyl) -N- (C 1 -C 6 alkyl) amino group, —C (＝ O) NH 2 , mono (C 1 -C 6 alkyl) aminocarbonyl group, di ( A C 1 -C 6 alkyl) aminocarbonyl group, a mono (C 1 -C 6 haloalkyl) aminocarbonyl group or a phenyl group;
    An aromatic heterocycle is
    Figure JPOXMLDOC01-appb-C000008
     A saturated heterocycle is
    Figure JPOXMLDOC01-appb-C000009
     Indicates that
    p 1 represents an integer of 0 to 5,
    p 2 represents an integer of 0 to 4,
    p 3 represents an integer of 0 to 3,
    p 4 represents an integer of 0 to 2,
    t represents an integer of 0 or 1]
    A 1-phenyl-1H-1,2,4-triazole derivative or a salt thereof, which is represented by the following formula:
PCT/JP2019/031563 2018-08-17 2019-08-09 3-(1h-1,2,4-triazole-1-yl) benzoic acid amide derivative and harmful organism control agent WO2020036133A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2018153421 2018-08-17
JP2018-153421 2018-08-17

Publications (1)

Publication Number Publication Date
WO2020036133A1 true WO2020036133A1 (en) 2020-02-20

Family

ID=69525531

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2019/031563 WO2020036133A1 (en) 2018-08-17 2019-08-09 3-(1h-1,2,4-triazole-1-yl) benzoic acid amide derivative and harmful organism control agent

Country Status (2)

Country Link
TW (1) TW202019889A (en)
WO (1) WO2020036133A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021175822A1 (en) 2020-03-02 2021-09-10 Syngenta Crop Protection Ag Pesticidally amidine-substituted benzoic acid amide compounds
CN115093373A (en) * 2022-08-24 2022-09-23 江苏省中国科学院植物研究所 1, 5-disubstituted-3-fluoroalkyl-1, 2, 4-triazole compound and preparation method and application thereof

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58225070A (en) * 1982-06-23 1983-12-27 Nippon Nohyaku Co Ltd Delta2-1,2,4-triazolin-5-one derivative and preparation and use thereof
JPH0710843A (en) * 1993-03-31 1995-01-13 Eisai Co Ltd Nitrogen-containing condensed heterocyclic compound
JPH0776578A (en) * 1992-11-12 1995-03-20 Bayer Ag Substituted triazolinone
WO1996016960A1 (en) * 1994-11-30 1996-06-06 Zeneca Limited Quinazoline derivatives
JPH08188563A (en) * 1993-12-27 1996-07-23 Eisai Co Ltd Anthranilic acid derivative
JP2001509145A (en) * 1996-12-23 2001-07-10 デュポン ファーマシューティカルズ カンパニー Heterocyclic aromatic compounds containing nitrogen as factor Xa inhibitors
JP2006513205A (en) * 2002-12-31 2006-04-20 ファイザー・プロダクツ・インク Benzamide inhibitor of P2X7 receptor
JP2006515313A (en) * 2002-11-15 2006-05-25 バーテックス　ファーマシューティカルズ　インコーポレイテッド Diaminotriazoles useful as inhibitors of protein kinases
JP2007284356A (en) * 2006-04-12 2007-11-01 Kumiai Chem Ind Co Ltd 3-triazolylphenyl sulfide derivative and agricultural and horticultural insecticide, acaricide and nematocide comprising the same as active ingredient
JP2008508216A (en) * 2004-07-27 2008-03-21 ノバルティス アクチエンゲゼルシャフト Quinazoline derivatives
JP2011500546A (en) * 2007-10-10 2011-01-06 アストラゼネカ・アクチエボラーグ Benzothiazoles as ghrelin receptor modulators
JP2014522873A (en) * 2011-08-12 2014-09-08 ビーエーエスエフ ソシエタス・ヨーロピア Anthranilamido compounds and their use as insecticides
CN108373453A (en) * 2018-04-03 2018-08-07 苏州大学张家港工业技术研究院 Triazole derivatives and preparation method thereof

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58225070A (en) * 1982-06-23 1983-12-27 Nippon Nohyaku Co Ltd Delta2-1,2,4-triazolin-5-one derivative and preparation and use thereof
JPH0776578A (en) * 1992-11-12 1995-03-20 Bayer Ag Substituted triazolinone
JPH0710843A (en) * 1993-03-31 1995-01-13 Eisai Co Ltd Nitrogen-containing condensed heterocyclic compound
JPH08188563A (en) * 1993-12-27 1996-07-23 Eisai Co Ltd Anthranilic acid derivative
WO1996016960A1 (en) * 1994-11-30 1996-06-06 Zeneca Limited Quinazoline derivatives
JP2001509145A (en) * 1996-12-23 2001-07-10 デュポン ファーマシューティカルズ カンパニー Heterocyclic aromatic compounds containing nitrogen as factor Xa inhibitors
JP2006515313A (en) * 2002-11-15 2006-05-25 バーテックス　ファーマシューティカルズ　インコーポレイテッド Diaminotriazoles useful as inhibitors of protein kinases
JP2006513205A (en) * 2002-12-31 2006-04-20 ファイザー・プロダクツ・インク Benzamide inhibitor of P2X7 receptor
JP2008508216A (en) * 2004-07-27 2008-03-21 ノバルティス アクチエンゲゼルシャフト Quinazoline derivatives
JP2007284356A (en) * 2006-04-12 2007-11-01 Kumiai Chem Ind Co Ltd 3-triazolylphenyl sulfide derivative and agricultural and horticultural insecticide, acaricide and nematocide comprising the same as active ingredient
JP2011500546A (en) * 2007-10-10 2011-01-06 アストラゼネカ・アクチエボラーグ Benzothiazoles as ghrelin receptor modulators
JP2014522873A (en) * 2011-08-12 2014-09-08 ビーエーエスエフ ソシエタス・ヨーロピア Anthranilamido compounds and their use as insecticides
CN108373453A (en) * 2018-04-03 2018-08-07 苏州大学张家港工业技术研究院 Triazole derivatives and preparation method thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021175822A1 (en) 2020-03-02 2021-09-10 Syngenta Crop Protection Ag Pesticidally amidine-substituted benzoic acid amide compounds
CN115093373A (en) * 2022-08-24 2022-09-23 江苏省中国科学院植物研究所 1, 5-disubstituted-3-fluoroalkyl-1, 2, 4-triazole compound and preparation method and application thereof

Also Published As

Publication number Publication date
TW202019889A (en) 2020-06-01

Similar Documents

Publication Publication Date Title
JP6234921B2 (en) Alkylphenyl sulfide derivatives and pest control agents
KR102638962B1 (en) 3-Alkoxybenzoic acid amide derivatives and pest control agents
JP2022185597A (en) Azole derivative, and use of the same
WO2020036133A1 (en) 3-(1h-1,2,4-triazole-1-yl) benzoic acid amide derivative and harmful organism control agent
TWI771418B (en) Pyrazole-3-carboxyamide derivatives and pest control agents
JP7305632B2 (en) Pyrazole derivatives and pesticides
WO2020036134A1 (en) 5-(1,2,4-triazole-5-yl) benzoic acid amide derivative and harmful organism control agent
JP2021121582A (en) 5-(pyrazole-5-yl)benzoic acid amide derivative and pest control agent
JP2021121581A (en) 3-(pyrazole-1-yl)benzoic acid amide derivative and pest control agent
TWI837454B (en) 3-alkoxy benzamide derivatives and pet control agent
JP7383850B2 (en) Heterocyclic compounds and their uses
RU2808434C2 (en) Pyrazole derivative and pest control agent
US11964957B2 (en) Pyrazole derivative and harmful organism-controlling agent
JP2021176836A (en) Alkoxyalkoxybenzene derivative having sulfur-containing substituent
JP2014108943A (en) 3-alkylthiophenyl oxime ether derivative and pest controlling agent

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19849709

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19849709

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP