WO2020036134A1 - Dérivé d'amide d'acide 5-(1,2,4-triazole-5-yl) benzoïque et agent de lutte contre les organismes nuisibles - Google Patents

Dérivé d'amide d'acide 5-(1,2,4-triazole-5-yl) benzoïque et agent de lutte contre les organismes nuisibles Download PDF

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WO2020036134A1
WO2020036134A1 PCT/JP2019/031564 JP2019031564W WO2020036134A1 WO 2020036134 A1 WO2020036134 A1 WO 2020036134A1 JP 2019031564 W JP2019031564 W JP 2019031564W WO 2020036134 A1 WO2020036134 A1 WO 2020036134A1
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group
alkyl
alkyl group
mono
substituent
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PCT/JP2019/031564
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Japanese (ja)
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幸浩 榎本
大介 志鎌
義浩 村松
寛起 近藤
啓二 鳥谷部
中谷　昌央
阿部　晋
陽 高根澤
松田　武
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クミアイ化学工業株式会社
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—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
    • 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

Definitions

  • the present invention relates to a novel 5- (1,2,4-triazol-5-yl) benzoic acid amide derivative or an agriculturally acceptable salt thereof, a pesticidal agent containing the derivative as an active ingredient, and a production intermediate It is about.
  • Patent Documents 1, 2, 3, and 4 disclose 5- (1,2,4-triazol-5-yl) benzoic acid amide derivatives that control fatty acid synthesis. And 4, the amine part of the amide bond is limited to a 1- [4- (substituted phenyl) piperidinyl] group. Furthermore, there is no description on pest control effect.
  • Patent Documents 5 and 6 describe 5- (1,2,4-triazol-5-yl) benzoic acid amide derivatives that control fatty acid synthesis, but the compounds described in Patent Documents 5 and 6 disclose ,
  • the amine part of the amide bond is limited to a 1- [3- (substituted phenyl) azetidinyl] group or a 1- [4- (substituted phenyl) piperidinyl group].
  • Patent Documents 7 and 8 describe 5- (1,2,4-triazol-5-yl) benzoic acid amide derivatives having a pest control effect, and the compounds described in Patent Documents 7 and 8 are described. Are limited to derivatives in which the 3-position of the triazole ring is substituted by a 1-methyl-3-pentafluoroethyl-4-trifluoromethylpyrazol-5-yl group.
  • Patent Documents 1, 2, 3, 4, 5 and 6 disclose that the amine part of the amide bond is other than a 1- [3- (substituted phenyl) azetidinyl] group or a 1- [4- (substituted phenyl) piperidinyl] group. There is no description about the derivative having the substituent. Furthermore, the 1-position of the triazole ring is limited to unsubstituted, and there is no description about the alkyl-substituted compound at the 1-position.
  • Patent Documents 7 and 8 disclose a 1-methyl-3-pentafluoroethyl-4-trifluoromethylpyrazol-5-yl group at the 3-position of the triazole ring and R 4 of the present compound [I]. There is no description of a substituent other than the combination where the site corresponding to is limited to a chlorine atom, and there is no description of the 5- (1,2,4-triazol-5-yl) benzoic acid amide derivative of the compound of the present invention.
  • 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 impact on the environment has been increasing, and the development of safer pest control agents has been desired.
  • pests that have acquired resistance to such pest control agents have appeared by using pest control agents such as insecticides and acaricides for many years. It is difficult to control.
  • the use of pesticides having high human toxicity is also 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. It is to provide a controlling agent.
  • the present inventors have synthesized various 5- (1,2,4-triazol-5-yl) benzoic acid amide derivatives and developed their physiological activities in order to develop a pesticidal agent having the preferable characteristics described above. Were studied diligently. As a result, the 5- (1,2,4-triazol-5-yl) benzoic acid amide derivative (hereinafter, referred to as the compound of the present invention) represented by the following general formula [I] exhibits excellent efficacy against various pests.
  • the present invention has been completed by conducting further research.
  • the present invention has the gist characterized by the following. (1) General formula [I]
  • R 1 and R 2 each independently represent a hydrogen atom, a C 1 -C 6 alkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 cycloalkyl C 1 -C 6 alkyl group, a C 2 -C 6 alkynyl group , C 2 -C 6 alkenyl group , C 2 -C 6 haloalkynyl group, C 2 -C 6 haloalkenyl group, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1- C 6 haloalkyl group, C 3 ⁇ C 6
  • substituted or poly-substituted phenyl C 1 ⁇ C 3 alkylsulfonyl C 1 ⁇ C 3 alkyl group selected from unsubstituted or substituent group ⁇ That is mono- or poly-substituted with a substituent heteroaryl C 1 ⁇ C 3 alkylthio C 1 ⁇ C 3 alkyl group, unsubstituted or mono- or poly-substituted heteroaryl with a substituent selected from substituent group ⁇ C 1 ⁇ C 3 alkylsulfinyl C 1 ⁇ C 3 alkyl group, a heteroaryl C 1 ⁇ C 3 alkylsulfonyl C 1 ⁇ C 3 monosubstituted or polysubstituted by unsubstituted or substituted group selected from substituent group ⁇ An alkyl group, a heterocycloalkyl C 1 -C 6 alkyl group, a C 1 -C 6 alkylcarbonyl C 1 -C
  • phenylcarbonyl C 1 ⁇ C 3 alkyl group Haitai monosubstituted or polysubstituted by unsubstituted or substituted group selected from substituent group ⁇ Arylcarbonyl C 1 ⁇ C 3 alkyl group, hydroxycarbonyl C 1 ⁇ C 6 alkyl group, C 1 ⁇ C 6 alkoxycarbonyl C 1 ⁇ C 3 alkyl group, a mono (C 1 ⁇ C 6 alkyl) aminocarbonyl C 1 ⁇ C 6 alkyl group, mono (C 1 -C 6 haloalkyl) aminocarbonyl C 1 -C 6 alkyl group, mono (C 3 -C 6 cycloalkyl) aminocarbonyl C 1 -C 6 alkyl group, mono (C 3 -C 6) Halocycloalkyl) aminocarbonyl C 1 -C 6 alkyl group, di (C 1 -C 6 alkyl) aminocarbonyl C 1 -C 6 alkyl group
  • R 6 may represent a hydrogen atom or a C 1 -C 6 alkyl group
  • R 7 is a hydrogen atom, a C 1 -C 6 alkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 cycloalkyl C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 A C 6 alkynyl group, a formyl group, a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxycarbonyl group, a C 1 -C 6 alkylsulfonyl group or a C 1 -C 6 haloalkylsulfonyl group,
  • Substituent group ⁇ is a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a hydroxy group,
  • a pest control agent comprising the 5- (1,2,4-triazol-5-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.
  • An agricultural chemical composition comprising, as an active ingredient, the 5- (1,2,4-triazol-5-yl) benzoic acid amide derivative or the agriculturally acceptable salt thereof according to (1) above, A method for controlling pests by simultaneously or separately acting on horticultural crops or agricultural horticultural crops where they are to be grown or where they are growing.
  • R 3 is a halogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a hydroxy group, 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, an amino group, a mono (C 1 -C 6 alkyl) amino group, a di (C 1 -C 6 alkyl) amino group, a carbamoyl group or a thiocarbamoyl group; R 4 is a halogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a hydroxy group, a C 1 -C 6 alkoxy group, a C 1 -C 6
  • substituted or poly-substituted phenyl C 1 ⁇ C 3 alkylsulfonyl C 1 ⁇ C 3 alkyl group selected from unsubstituted or substituent group ⁇ That is mono- or poly-substituted with a substituent heteroaryl C 1 ⁇ C 3 alkylthio C 1 ⁇ C 3 alkyl group, unsubstituted or mono- or poly-substituted heteroaryl with a substituent selected from substituent group ⁇ C 1 ⁇ C 3 alkylsulfinyl C 1 ⁇ C 3 alkyl group, a heteroaryl C 1 ⁇ C 3 alkylsulfonyl C 1 ⁇ C 3 monosubstituted or polysubstituted by unsubstituted or substituted group selected from substituent group ⁇ An alkyl group, a heterocycloalkyl C 1 -C 6 alkyl group, a C 1 -C 6 alkylcarbonyl C 1 -C
  • phenylcarbonyl C 1 ⁇ C 3 alkyl group Haitai monosubstituted or polysubstituted by unsubstituted or substituted group selected from substituent group ⁇ Arylcarbonyl C 1 ⁇ C 3 alkyl group, hydroxycarbonyl C 1 ⁇ C 6 alkyl group, C 1 ⁇ C 6 alkoxycarbonyl C 1 ⁇ C 3 alkyl group, a mono (C 1 ⁇ C 6 alkyl) aminocarbonyl C 1 ⁇ C 6 alkyl group, mono (C 1 -C 6 haloalkyl) aminocarbonyl C 1 -C 6 alkyl group, mono (C 3 -C 6 cycloalkyl) aminocarbonyl C 1 -C 6 alkyl group, mono (C 3 -C 6) Halocycloalkyl) aminocarbonyl C 1 -C 6 alkyl group, di (C 1 -C 6 alkyl) aminocarbonyl C 1 -C 6 alkyl group
  • R 6 and R 8 each independently represent a hydrogen atom or a C 1 -C 6 alkyl group
  • R 7 is a hydrogen atom, a C 1 -C 6 alkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 cycloalkyl C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 A C 6 alkynyl group, a formyl group, a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxycarbonyl group, a C 1 -C 6 alkylsulfonyl group or a C 1 -C 6 haloalkylsulfonyl group
  • Substituent group ⁇ is a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a hydroxy
  • R 3 is a halogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a hydroxy group, 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, an amino group, a mono (C 1 -C 6 alkyl) amino group, a di (C 1 -C 6 alkyl) amino group, a carbamoyl group or a thiocarbamoyl group; R 4 is a halogen atom, a cyano group, a C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group, a hydroxy group, a C 1 -C 6 alkoxy group, a C 1 -C 6
  • substituted or poly-substituted phenyl C 1 ⁇ C 3 alkylsulfonyl C 1 ⁇ C 3 alkyl group selected from unsubstituted or substituent group ⁇ That is mono- or poly-substituted with a substituent heteroaryl C 1 ⁇ C 3 alkylthio C 1 ⁇ C 3 alkyl group, unsubstituted or mono- or poly-substituted heteroaryl with a substituent selected from substituent group ⁇ C 1 ⁇ C 3 alkylsulfinyl C 1 ⁇ C 3 alkyl group, a heteroaryl C 1 ⁇ C 3 alkylsulfonyl C 1 ⁇ C 3 monosubstituted or polysubstituted by unsubstituted or substituted group selected from substituent group ⁇ An alkyl group, a heterocycloalkyl C 1 -C 6 alkyl group, a C 1 -C 6 alkylcarbonyl C 1 -C
  • phenylcarbonyl C 1 ⁇ C 3 alkyl group Haitai monosubstituted or polysubstituted by unsubstituted or substituted group selected from substituent group ⁇ Arylcarbonyl C 1 ⁇ C 3 alkyl group, hydroxycarbonyl C 1 ⁇ C 6 alkyl group, C 1 ⁇ C 6 alkoxycarbonyl C 1 ⁇ C 3 alkyl group, a mono (C 1 ⁇ C 6 alkyl) aminocarbonyl C 1 ⁇ C 6 alkyl group, mono (C 1 -C 6 haloalkyl) aminocarbonyl C 1 -C 6 alkyl group, mono (C 3 -C 6 cycloalkyl) aminocarbonyl C 1 -C 6 alkyl group, mono (C 3 -C 6) Halocycloalkyl) aminocarbonyl C 1 -C 6 alkyl group, di (C 1 -C 6 alkyl) aminocarbonyl C 1 -C 6 alkyl group
  • R 6 represents a hydrogen atom or a C 1 -C 6 alkyl group
  • R 7 is a hydrogen atom, a C 1 -C 6 alkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 cycloalkyl C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 A C 6 alkynyl group, a formyl group, a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxycarbonyl group, a C 1 -C 6 alkylsulfonyl group or a C 1 -C 6 haloalkylsulfonyl group
  • R 9 represents a hydrogen atom, a halogen atom or a cyano group
  • Substituent group ⁇ is a halogen atom, a C 1 -C 6 alkyl group,
  • Pest control agents containing the compound of the present invention include stink bug pests, lepidopteran pests, nematodes, fly flies, wasps, pests, grasshoppers, thrips, mites, plant parasitic nematodes It shows an excellent control effect on a wide range of pests such as insects, 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.
  • notations such as “C 1 -C 6 ” indicate that the number of carbon atoms of the subsequent substituent is 1 to 6 in this case.
  • the “C 1 -C 6 alkyl group” refers to a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, unless otherwise specified.
  • 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. be able to.
  • the “C 3 -C 6 cycloalkyl C 1 -C 6 alkyl group” means that the cycloalkyl portion and the alkyl portion have the above-mentioned meanings unless otherwise specified (C 3 -C 6 cycloalkyl)-.
  • C 2 -C 6 alkenyl group refers to a linear or branched alkenyl group having 2 to 6 carbon atoms, unless otherwise specified. Examples thereof include vinyl, 1-propenyl, and isopropenyl.
  • C 3 -C 6 cycloalkyl C 2 -C 6 alkenyl group means that the cycloalkyl portion and the alkenyl portion have the same meaning as described above, unless otherwise specified (C 3 -C 6 cycloalkyl)-.
  • C 2 -C 6 alkynyl group means a straight-chain or branched-chain alkynyl group having 2 to 6 carbon atoms, unless otherwise specified.
  • C 3 -C 6 cycloalkyl C 2 -C 6 alkynyl group means that the cycloalkyl portion and the alkynyl portion have the above meanings unless otherwise specified (C 3 -C 6 cycloalkyl)-.
  • C 2 -C 6 haloalkynyl group means a straight-chain or branched-chain having 2 to 6 carbon atoms, which is substituted with the same or different 1 to 9 halogen atoms, unless otherwise specified.
  • 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- Dichlorovinyl, 2,2-dichlorovinyl, trichlorovinyl, 1,2-dibromovinyl, 2,2-dibromovinyl, tribromovinyl, 1,2-diiodovinyl, 2,2-diiodovinyl, triiodovinyl, 1-fluoro -2-propenyl, 2-fluoro-2-propenyl, 3-fluoro-2-propenyl, 2,3-difluorovinyl, 1,2-
  • C 1 -C 6 haloalkyl group means a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, which is substituted with the same or different halogen atoms 1 to 13, unless otherwise specified.
  • the “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.
  • 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.
  • 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.
  • a "C 3 ⁇ C 6 halocycloalkyl C 1 ⁇ C 6 alkyl group” unless otherwise specified, halocycloalkyl moiety and the alkyl group is a meaning of the (C 3 ⁇ C 6 Haroshikuro Alkyl)-(C 1 -C 6 alkyl)-group, such as 2,2-difluorocyclopropylmethyl, 2,2-dichlorocyclopropylmethyl, 1- (2,2-difluorocyclopropyl) ethyl, -(2,2-difluorocyclopropyl) ethyl, 1- (2,2-dichlorocyclopropyl) ethyl, 2- (2,2-dichlorocyclopropyl) ethyl, 2- (2,2-difluorocyclopropyl) propyl , 3,3-difluorocyclobutylmethyl, 2,2,3,3-tetrafluorocyclobutylmethyl
  • phenyl C 1 -C 3 alkyl group refers to a (phenyl)-(C 1 -C 3 alkyl) group unless otherwise specified, and includes, for example, benzyl, 1-phenylethyl, 2-phenyl Examples include groups such as ethyl or 2-phenylpropyl.
  • phenyl C 1 -C 3 haloalkyl group refers to a (phenyl)-(C 1 -C 3 haloalkyl) group unless otherwise specified, and includes 2-phenyl-2,2-difluoroethyl and the like. Groups can be mentioned.
  • a “heteroaryl group” means a 5- or 6-membered single-membered group having 1 to 6 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom in addition to a carbon atom, unless otherwise specified.
  • a ring heterocycle for example, thiophen-2-yl, thiophen-3-yl, furan-2-yl, furan-3-yl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, Oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl , Thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-1-yl, imidazo -2-yl, imidazol-4-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, 1,3,4-oxadiazol-2-yl
  • heteroaryl C 1 -C 3 alkyl group refers to a (heteroaryl)-(C 1 -C 3 alkyl) group in which the heteroaryl portion has the same meaning as described above, unless otherwise limited.
  • heteroaryl C 1 -C 3 haloalkyl group means a (heteroaryl)-(C 1 -C 3 haloalkyl) group in which the heteroaryl portion has the above-mentioned meaning, unless otherwise specified.
  • 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 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 3-cyanopropyl, 2-cyanopropan-2-yl, 1-cyanobutyl, 4-cyanobutyl, 5-cyanopentyl or 6-cyanohexyl; Can be.
  • cyano C 3 -C 6 cycloalkyl group refers to a (cyano)-(C 3 -C 6 cycloalkyl) group in which the cycloalkyl moiety has the above-mentioned meaning, unless otherwise specified. , 1-cyanocyclopropyl, 2-cyanocyclopropyl, 1-cyanocyclobutyl, 3-cyanocyclobutyl, 1-cyanocyclopentyl and the like.
  • the “C 1 -C 6 alkoxycarbonyl C 3 -C 6 cycloalkyl group” means that the alkoxycarbonyl portion and the cycloalkyl portion have the above-mentioned meanings (C 1 -C 6 alkoxy), unless otherwise specified.
  • hydroxy C 1 -C 6 alkyl group refers to a (hydroxy)-(C 1 -C 6 alkyl) group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified. , 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxybutyl or 4-hydroxybutyl.
  • 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 -C 6 alkyl)-group, for example, methoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 2-ethoxypropyl, 3-ethoxypropyl, Examples include groups such as 1-methyl-3-methoxybutyl or 3-butoxybutyl.
  • the “mono (C 1 -C 6 alkyl) amino group” refers to a (C 1 -C 6 alkyl) -NH— group in which the alkyl portion has the above meaning, unless otherwise specified.
  • Examples include groups such as methylamino, ethylamino, n-propylamino or isopropylamino.
  • 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, diethylamino and N-ethyl-N-methylamino.
  • Examples include groups such as butanoyl, 3,3-dimethylbutanoyl, pentanoyl, 2-methylpentanoyl, 3-methylpentanoyl, 4-methylpentanoyl, and hexanoyl.
  • examples thereof include groups such as cyclopropanecarbonyl, cyclobutanecarbonyl, cyclopentanecarbonyl and cyclohexanecarbonyl.
  • the two alkyl groups may be different from each other, for example, dimethylaminocarbonyl, diethylaminocarbonyl, di (n-propyl) aminocarbonyl, diisopropylaminocarbonyl, dibutylaminocarbonyl, N-ethyl-N- Methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-isopropyl-N-methylaminocarbonyl, N-butyl-N-methylaminocarbonyl, N- (sec-butyl) -N-methylaminocarbonyl, N- Isobutyl-N-methylaminocarbonyl, N-pentyl-N-methylamino Carbonyl, N- ethyl -N- propyl aminocarbonyl, mention may be made of N- ethyl -N- isopropyl aminocarbonyl or N- ethyl -N- butyl
  • C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkylamino group means, for example, methoxycarbonylmethylamino, ethoxycarbonylmethylamino, tert-butoxycarbonylmethylamino or 1- Examples of the group include [1- (tert-butoxycarbonyl) ethyl] amino.
  • “mono (C 1 -C 6 alkoxycarbonyl) amino group” means, for example, methoxycarbonylamino, ethoxycarbonylamino, isopropoxycarbonylamino, tert-butoxycarbonylamino or isobutoxycarbonyl unless otherwise specified. Examples include groups such as amino.
  • groups such as methylthiocarbonyl, ethylthiocarbonyl and isopropylthiocarbonyl can be mentioned.
  • Groups can be mentioned.
  • (C 1 -C 6 alkoxy) thiocarbonyl group means, unless otherwise specified, an alkyl moiety having the above meaning (C 1 -C 6 alkyl) -OC (OS) —. And represents, for example, methoxythiocarbonyl, ethoxythiocarbonyl, n-propoxythiocarbonyl, isopropoxythiocarbonyl, n-butoxythiocarbonyl, isobutoxythiocarbonyl, sec-butoxythiocarbonyl, tert-butoxythiocarbonyl, n- Pentoxythiocarbonyl, 1-methylbutoxythiocarbonyl, 2-methylbutoxythiocarbonyl, 3-methylbutoxythiocarbonyl, 1-ethylpropoxythiocarbonyl, 1,1-dimethylpropoxythiocarbonyl, 1,2-dimethylpropoxythiocarbonyl Or 2, - there can be mentioned groups such as dimethylpropoxy thiocarbonyl.
  • the two alkyl groups may be different from each other, for example, dimethylaminothiocarbonyl, diethylaminothiocarbonyl, di (n-propyl) aminothiocarbonyl, diisopropylaminothiocarbonyl, dibutylaminothiocarbonyl , N-ethyl-N-methylaminothiocarbonyl, N-methyl-N-propylaminothiocarbonyl, N-isopropyl-N-methylaminothiocarbonyl, N-butyl-N-methylaminothiocarbonyl, N- (sec- Butyl) -N-methylaminothiocarbonyl, N-isobutyl-N-methyla Groups such as nothiocarbonyl, N-pentyl-N-methylaminothiocarbonyl, N-ethyl-N-propylaminothiocarbonyl, N-ethyl-N-is
  • Examples include groups such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl and tert-butylsulfonyl.
  • difluoromethylsulfonyl difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, 3,3,3-trifluoropropylsulfonyl, heptafluoropropylsulfonyl, or heptafluoro And groups such as -2-propylsulfonyl.
  • methylaminosulfonyl ethylaminosulfonyl, n-propylaminosulfonyl, isopropylaminosulfonyl, n-butylaminosulfonyl, isobutylaminosulfonyl, sec-butylaminosulfonyl, tert-butylaminosulfonyl, n-pentyl Aminosulfonyl, 1-methylbutylaminosulfonyl, 2-methylbutylaminosulfonyl, 3-methylbutylaminosulfonyl, 1-ethylpropylaminosulfonyl, 1,1-dimethylpropylaminosulfonyl, 1,2-dimethylpropylaminosulfonyl, Include a 2-dimethylpropyl aminosulfonyl or n- hexyl aminosulfonyl like groups.
  • the “di (C 1 -C 6 alkyl) aminosulfonyl group” means that the alkyl portion has the above-mentioned meaning (C 1 -C 6 alkyl) 2 —NS (-O), unless otherwise specified.
  • two alkyl groups may be different from each other, for example, dimethylamino sulfonyl, diethylamino sulfonyl, di (n- propyl) aminosulfonyl, diisopropylamino sulfonyl, dibutyl aminosulfonyl, N- ethyl - N-methylaminosulfonyl, N-methyl-N-propylaminosulfonyl, N-isopropyl-N-methylaminosulfonyl, N-butyl-N-methylaminosulfonyl, N- (sec-butyl) -N-methylaminosulfonyl, N-isobutyl-N-methylaminosulfonyl, N-pentyl-N-methyla
  • Examples include groups such as minosulfonyl, N-ethyl-N-propylaminosulfocarbonyl, N-
  • aminocarbonyl C 1 -C 6 alkyl group means, unless otherwise specified, H 2 NC (-O)-(C 1 -C 6 alkyl)-wherein the alkyl portion has the above-mentioned meaning. And carbamoylmethyl, 1-carbamoylethyl, 2-carbamoylethyl, and the like.
  • the term “mono (C 1 -C 6 alkyl) aminocarbonyl C 1 -C 6 alkyl group” means (C 1 -C 6 alkyl) -NH in which the alkyl moiety is as defined above, unless otherwise specified.
  • Represents a -C ( O)-(C 1 -C 6 alkyl)-group, for example, a group such as N-methylcarbamoylmethyl, N-ethylcarbamoylmethyl or N- (tert-butyl) carbamoylmethyl; it can.
  • the term “mono (C 1 -C 6 haloalkyl) aminocarbonyl C 1 -C 6 alkyl group” means (C 1 -C 6 haloalkyl) -NH in which the haloalkyl portion is as defined above, unless otherwise specified.
  • di (C 1 -C 6 alkyl) aminocarbonyl C 1 -C 6 alkyl group means (C 1 -C 6 alkyl) 2- in which the alkyl portion has the above-mentioned meaning, unless otherwise specified.
  • Represents an NC ( O)-(C 1 -C 6 alkyl)-group, wherein the two alkyl groups may be different from each other, for example, N, N-dimethylcarbamoylmethyl, N, N-diethylcarbamoyl
  • examples of such groups include methyl, N, N-dipropylcarbamoylmethyl, N-ethyl-N-methylcarbamoylmethyl, and N-methyl-N-propylcarbamoylmethyl.
  • C 1 -C 6 alkoxyimino group refers to a (C 1 -C 6 alkyl) -ONOC— group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified. , Methoxyimino, ethoxyimino or isopropoxyimino.
  • a C 1 -C 6 alkyl) group for example, 1- (methoxyimino) ethyl, 2- (methoxyimino) ethyl, 1- (methoxyimino) propyl, 2- (methoxyimino) propyl, 3- (methoxyimino) ) Propyl, 1- (ethoxyimino) ethyl, 2- (ethoxyimino) ethyl, 1- (ethoxyimino) propyl, 2- (ethoxyimino) propyl, 3- (ethoxyimino) propyl, 1- (isopropoxyimino) Examples include groups such as ethyl or 2- (isopropoxyimino) ethyl.
  • a (C 1 -C 6 alkyl) group for example, 2- (2,2-difluoroethoxyimino) ethyl, 2- (2,2,2-trifluoroethoxyimino) ethyl, 2- (2,2 Examples include groups such as 2-trifluoroethoxyimino) propyl and 3- (2,2,2-trifluoroethoxyimino) propyl.
  • heterocycloalkyl group refers to a 3- to 6-membered saturated heterocycle containing at least one atom selected from an oxygen atom, a nitrogen atom and a sulfur atom in addition to a carbon atom, unless otherwise specified.
  • groups such as oxetan-2-yl, oxetan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl or tetrahydropyran-4-yl Can be mentioned.
  • heterocycloalkyl C 1 ⁇ C 6 alkyl group unless otherwise specified, the heterocycloalkyl moiety and the alkyl moiety is the meaning of the (C 3 ⁇ C 6 heterocycloalkyl) - (C Represents a ( 1 -C 6 alkyl) group, for example, (oxetan-3-yl) methyl, (tetrahydrofuran-2-yl) methyl, (tetrahydrofuran-3-yl) methyl, (tetrahydropyran-2-yl) methyl , (Tetrahydropyran-3-yl) methyl or (tetrahydropyran-4-yl) methyl.
  • C Represents a ( 1 -C 6 alkyl) group for example, (oxetan-3-yl) methyl, (tetrahydrofuran-2-yl) methyl, (tetrahydrofuran-3-yl) methyl, (tetrahydropyran-2-y
  • C 1 -C 6 alkylthio group means a (C 1 -C 6 alkyl) -S— group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified.
  • methylthio, ethylthio examples include groups such as n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio and tert-butylthio.
  • groups such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl and tert-butylsulfinyl.
  • the “C 1 -C 6 haloalkoxy C 1 -C 6 alkyl group” means that the haloalkoxy moiety has the above-mentioned meaning, unless otherwise specified, as (C 1 -C 6 haloalkoxy)-(C 1 ⁇ C 6 alkyl)-group, for example, 2- (difluoromethoxy) ethyl, 2- (trifluoromethoxy) ethyl, 2- (2,2-difluoroethoxy) ethyl or 2- (2,2,2- Groups such as (trifluoroethoxy) ethyl can be exemplified.
  • C 1 -C 6 haloalkoxy C 1 -C 6 haloalkyl group means that the haloalkoxy moiety and the haloalkyl moiety have the same meaning as described above (C 1 -C 6 haloalkoxy)-unless otherwise specified.
  • a (C 1 -C 6 haloalkyl)-group for example, 1,1,2-trifluoro-2- (trifluoromethoxy) ethyl, 1,1,2-trifluoro-2- (pentafluoroethoxy) ethyl Or a group such as 1,1,2-trifluoro-2- (heptafluoropropoxy) ethyl.
  • C 3 -C 6 cycloalkoxy C 1 -C 6 alkyl group means that the cycloalkoxy portion and the alkyl portion have the above-mentioned meanings, unless otherwise specified (C 3 -C 6 cycloalkoxy)-.
  • a (C 1 -C 6 alkyl) group for example, cyclopropyloxymethyl, 1- (cyclopropyloxy) ethyl, 2- (cyclopropyloxy) ethyl, 2- (cyclopropyloxy) ethyl, 2- (cyclo Propyloxy) propyl, 3- (cyclopropyloxy) propyl, 2- (cyclopropyloxy) propyl, 3- (cyclopropyloxy) propyl, 1-methyl-3- (cyclopropyloxy) butyl or 3- (cyclopropyl Oxy) butyl, cyclobutyloxymethyl, cyclopentyloxymethyl, cyclohexyl
  • groups such as oxymethyl.
  • a "C 3 ⁇ C 6 halocycloalkyl alkoxy C 1 ⁇ C 6 alkyl group” unless otherwise specified, halo cycloalkoxy moiety and the alkyl moiety is the meaning of the (C 3 ⁇ C 6 Haroshikuro An alkoxy)-(C 1 -C 6 alkyl) group, for example, 2,2-difluorocyclopropyloxymethyl, 2,2-dichlorocyclopropyloxymethyl, 1- (2,2-difluorocyclopropyloxy) ethyl , 2- (2,2-difluorocyclopropyloxy) ethyl, 1- (2,2-dichlorocyclopropyloxy) ethyl, 2- (2,2-dichlorocyclopropyloxy) ethyl, 2- (2,2- Difluorocyclopropyloxy) propyl, 3,3-difluorocyclobutyloxymethyl, 3,3-difluorocyclo
  • the “mercapto C 1 -C 6 alkyl group” refers to an HS- (C 1 -C 6 alkyl)-group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified.
  • mercaptomethyl examples include groups such as 1-mercaptoethyl or 2-mercaptoethyl.
  • C 1 -C 6 alkylthio C 1 -C 6 alkyl group means that the alkyl moiety has the above-mentioned meaning unless otherwise specified, and is (C 1 -C 6 alkyl) -S- (C 1 -C 6 -alkyl).
  • a C 6 alkyl)-group such as methylthiomethyl, ethylthiomethyl, n-propylthiomethyl, isopropylthiomethyl, 1- (methylthio) ethyl, 2- (methylthio) ethyl, 2- (ethylthio) ethyl, -(N-propylthio) ethyl, 2- (n-propylthio) ethyl, 1- (isopropylthio) ethyl, 2- (isopropylthio) ethyl, 1- (methylthio) propyl, 2- (methylthio) propyl, 3- ( Methylthio) propyl, 1- (ethylthio) propyl, 2- (ethylthio) propyl, 3- (ethylthio) propyl, 1- (n-propyl Pyrthio) propyl, 2- (n-propylthio) propyl, 3- (n
  • a-(C 1 -C 6 alkyl)-group for example, methylsulfinylmethyl, ethylsulfinylmethyl, n-propylsulfinylmethyl, isopropylsulfinylmethyl, 1- (methylsulfinyl) ethyl, 2- (methylsulfinyl) ethyl, 2- (ethylsulfinyl) ethyl, 1- (n-propylsulfinyl) ethyl, 2- (n-propylsulfinyl) ethyl, 1- (isopropylsulfinyl) ethyl, 2- (isopropylsulfinyl) ethyl, 1- (methylsulfinyl) Propyl, 2- (methylsulfinyl) propyl, 3- Methylsulfinyl) propyl, 1- (ethylsulfin
  • a 2- (C 1 -C 6 alkyl)-group for example, methylsulfonylmethyl, ethylsulfonylmethyl, n-propylsulfonylmethyl, isopropylsulfonylmethyl, 1- (methylsulfonyl) ethyl, 2- (methylsulfonyl) ethyl , 2- (ethylsulfonyl) ethyl, 1- (n-propylsulfonyl) ethyl, 2- (n-propylsulfonyl) ethyl, 1- (isopropylsulfonyl) ethyl, 2- (isopropylsulfonyl) ethyl, 1- (methylsulfonyl) ) Propyl, 2- (methylsulfonyl) propyl, 3- (methylsulfonyl) pro 1- (ethylsulfonyl)
  • C 1 -C 6 haloalkylthio C 1 -C 6 alkyl group means that the haloalkyl portion and the alkyl portion have the above-mentioned meanings unless otherwise specified (C 1 -C 6 haloalkyl) -S-.
  • a (C 1 -C 6 alkyl)-group for example, 2- (difluoromethylthio) ethyl, 2- (trifluoromethylthio) ethyl, 2- (2,2-difluoroethylthio) ethyl, 2- (2 2,2-trifluoroethylthio) ethyl, 2- (3,3-difluoropropylthio) ethyl, 2- (3,3,3-trifluoroethylthio) ethyl, 3- (difluoromethylthio) propyl, 3- (Trifluoromethylthio) propyl, 3- (2,2-difluoroethylthio) propyl, 3- (2,2,2-trifluoroethylthio) propyl, 3 Groups such as (3,3-difluoropropylthio) propyl, 3- (3,3,3-trifluoropropylthio) propyl, 4- (tri
  • C 1 -C 6 haloalkylsulfonyl C 1 -C 6 alkyl group means, unless otherwise specified, a haloalkyl moiety and an alkyl moiety having the above meanings (C 1 -C 6 haloalkyl) -S ( OO) 2- (C 1 -C 6 alkyl) -group, for example, 2- (difluoromethylsulfonyl) ethyl, 2- (trifluoromethylsulfonyl) ethyl, 2- (2,2-difluoroethylsulfonyl) Ethyl, 2- (2,2,2-trifluoroethylsulfonyl) ethyl, 2- (3,3-difluoropropylsulfonyl) ethyl, 2- (3,3,3-trifluoroethylsulfonyl) ethyl, 3- ( Difluoro
  • the “C 3 -C 6 cycloalkylthio C 1 -C 6 alkyl group” means that the cycloalkyl portion and the alkyl portion have the same meanings as described above (C 3 -C 6 cycloalkyl)-unless otherwise specified. And represents an S- (C 1 -C 6 alkyl)-group, such as cyclopropylthiomethyl, cyclopentylthiomethyl, 1- (cyclopropylthio) ethyl or 2- (cyclopropylthio) ethyl. it can.
  • the “C 3 -C 6 cycloalkylsulfinyl C 1 -C 6 alkyl group” means that the cycloalkyl portion and the alkyl portion have the above-mentioned meanings (C 3 -C 6 cycloalkyl) unless otherwise specified.
  • —S (-O) — (C 1 -C 6 alkyl) — represents a group such as cyclopropylsulfinylmethyl, cyclopentylsulfinylmethyl, 1- (cyclopropylsulfinyl) ethyl or 2- (cyclopropylsulfinyl) ethyl; Groups can be mentioned.
  • the “C 3 -C 6 cycloalkylsulfonyl C 1 -C 6 alkyl group” means that the cycloalkyl portion and the alkyl portion have the above-mentioned meanings (C 3 -C 6 cycloalkyl) unless otherwise specified.
  • —S ( O) 2 — (C 1 -C 6 alkyl) — group, for example, cyclopropylsulfonylmethyl, cyclopentylsulfonylmethyl, 1- (cyclopropylsulfonyl) ethyl or 2- (cyclopropylsulfonyl) ethyl and the like
  • the “C 3 -C 6 halocycloalkylthio C 1 -C 6 alkyl group” means that the halocycloalkyl portion and the alkyl portion have the above-mentioned meanings (C 3 -C 6 halocycloalkyl), unless otherwise specified.
  • Alkyl) -S- (C 1 -C 6 alkyl)-group such as 2,2-difluorocyclopropylthiomethyl, 1- (2,2-difluorocyclopropylthio) ethyl or 2- (2,2 And groups such as -difluorocyclopropylthio) ethyl.
  • the “C 3 -C 6 halocycloalkylsulfinyl C 1 -C 6 alkyl group” means that the halocycloalkyl portion and the alkyl portion have the above-mentioned meanings (C 3 -C 6 halo) unless otherwise specified.
  • C 3 -C 6 halocycloalkylsulfonyl C 1 -C 6 alkyl group means that the halocycloalkyl portion and the alkyl portion have the above-mentioned meanings (C 3 -C 6 halo) unless otherwise specified.
  • Cycloalkyl) —S ( O) 2 — (C 1 -C 6 alkyl) — group, such as 2,2-difluorocyclopropylsulfonylmethyl, 1- (2,2-difluorocyclopropylsulfonyl) ethyl or Groups such as 2- (2,2-difluorocyclopropylsulfonyl) ethyl and the like can be mentioned.
  • C 1 -C 6 alkylsulfonyloxy C 1 -C 6 alkyl group means that the alkylsulfonyloxy portion and the alkyl portion have the above-mentioned meanings (C 1 -C 6 alkyl) unless otherwise specified.
  • C 1 -C 6 alkylcarbonylthio C 1 -C 3 alkyl group means that the alkylcarbonylthio portion and the alkyl portion have the above-mentioned meanings (C 1 -C 6 alkyl) unless otherwise specified.
  • -C ( O) -S- (C 1 -C 3 alkyl)-represents a group such as methylcarbonylthiomethyl.
  • amino C 1 -C 6 alkyl group refers to an H 2 N— (C 1 -C 6 alkyl) group in which the alkyl portion has the above-mentioned meaning, unless otherwise specified. , 1-aminoethyl, 2-aminoethyl, 1-aminopropyl, 3-aminopropyl, 2-aminopropan-2-yl, 1-aminobutyl, 4-aminobutyl, 5-aminopentyl or 6-aminohexyl and the like And the group of
  • the “mono (C 1 -C 6 haloalkylcarbonyl) amino C 1 -C 6 alkyl group” means that the haloalkyl portion and the alkyl portion have the above-mentioned meanings (C 1 -C 6 haloalkyl), unless otherwise specified.
  • C 1 -C 6 alkyl)-group such as chloroacetylaminomethyl, dichloroacetylaminomethyl, difluoroacetylaminomethyl, trifluoroacetylaminomethyl, 1- (tri Examples include groups such as fluoroacetylamino) ethyl, 2- (trifluoroacetylamino) ethyl, 1- (difluoroacetylamino) ethyl, and 2- (difluoroacetylamino) ethyl.
  • the “mono (C 1 -C 6 alkoxycarbonyl) amino C 1 -C 6 alkyl group” means that the alkoxy portion and the alkyl portion have the above-mentioned meanings (C 1 -C 6 alkoxy) unless otherwise specified.
  • the “mono (C 1 -C 6 alkyl) aminocarbonylamino C 1 -C 6 alkyl group” means that the alkyl portion has the above-mentioned meaning (C 1 -C 6 alkyl)-unless otherwise specified.
  • NH—C ( O) —NH— (C 1 -C 6 alkyl) — group, for example, methylaminocarbonylaminomethyl, ethylaminocarbonylaminomethyl, isopropylaminocarbonylaminomethyl or tert-butylaminocarbonylaminomethyl And the like.
  • the term “di (C 1 -C 6 alkyl) aminocarbonylamino C 1 -C 6 alkyl group” means that the alkyl portion has the above-mentioned meaning (C 1 -C 6 alkyl) 2 unless otherwise specified.
  • Represents an NC ( O) -NH- (C 1 -C 6 alkyl)-group, wherein the alkyl groups may be different from each other, for example, dimethylaminocarbonylaminomethyl, diethylaminocarbonylaminomethyl or N-methyl- And groups such as N-ethylaminocarbonylaminomethyl.
  • “mono (C 1 -C 6 alkylsulfonyl) amino C 1 -C 6 alkyl group” means, unless otherwise specified, an alkyl moiety having the above-mentioned meaning (C 1 -C 6 alkyl) -S.
  • ( O) 2 —NH— (C 1 -C 6 alkyl) — group, for example, 2- (methylsulfonylamino) ethyl, 2- (ethylsulfonylamino) ethyl, 2- (isopropylsulfonylamino) ethyl, Examples include groups such as 3- (methylsulfonylamino) propyl or 4- (methylsulfonylamino) butyl.
  • the “mono (C 1 -C 6 haloalkylsulfonyl) amino C 1 -C 6 alkyl group” means that the haloalkyl portion and the alkyl portion have the above-mentioned meanings (C 1 -C 6 haloalkyl) unless otherwise specified.
  • N- (C 1 -C 6 alkylsulfonyl) -N- (C 1 -C 6 alkyl) amino C 1 -C 6 alkyl group refers to the above amino C 1 -C 6 unless otherwise specified.
  • N- (C 1 -C 6 haloalkylsulfonyl) -N- (C 1 -C 6 alkyl) amino C 1 -C 6 alkyl group refers to the above amino C 1 -C 6- unless otherwise specified.
  • a group in which two hydrogen atoms of an amino group of a C 6 alkyl group are respectively substituted with a (C 1 -C 6 haloalkyl) -S ( O) 2 -group and a (C 1 -C 6 alkyl) -group;
  • (N-difluoromethylsulfonyl-N-methyl) aminomethyl (N-trifluoromethylsulfonyl-N-methyl) aminomethyl, (N-nonafluorobutylsulfonyl-N-methyl) aminomethyl, (N-difluoro Methylsulfonyl-N-ethyl) aminomethyl, (N-trifluoromethylsulfonyl-N-ethyl) aminomethyl or (N-nonafluorobutylsulfonyl) Can be exemplified -N- ethyl) amino group, such as methyl.
  • phenyloxy C 1 -C 3 alkyl group refers to a (phenyl) -O- (C 1 -C 3 alkyl)-group unless otherwise specified.
  • phenoxymethyl, 1-phenoxy Examples include groups such as ethyl or 2-phenoxyethyl.
  • heteroaryloxy C 1 -C 3 alkyl group means a (heteroaryl) -O- (C 1 -C 3 alkyl) -group in which the heteroaryl portion has the above-mentioned meaning, unless otherwise specified.
  • a "phenyl C 1 ⁇ C 3 alkoxy C 1 ⁇ C 3 alkyl group” unless specifically limited, (phenyl) - (C 1 ⁇ C 3 alkyl) -O- (C 1 ⁇ C 3 alkyl )-, And examples thereof include groups such as benzyloxymethyl, 1-benzyloxyethyl and 2-benzyloxyethyl.
  • heteroaryl C 1 -C 3 alkoxy C 1 -C 3 alkyl group means a (heteroaryl)-(C 1 -C 3 alkyl) in which the heteroaryl portion has the above-mentioned meaning, unless otherwise limited.
  • phenylthio C 1 -C 3 alkyl group refers to a (phenyl) -S- (C 1 -C 3 alkyl)-group unless otherwise specified, and examples thereof include phenylthiomethyl and 1-phenyl Groups such as thioethyl or 2-phenylthioethyl can be mentioned.
  • phenylsulfinyl Examples include groups such as methyl, 1-phenylsulfinylethyl, and 2-phenylsulfinylethyl.
  • Examples include groups such as sulfonylmethyl, 1-phenylsulfonylethyl, and 2-phenylsulfonylethyl.
  • heteroarylthio C 1 -C 3 alkyl group means, unless otherwise limited, a heteroaryl moiety having the same meaning as described above, (heteroaryl) -S- (C 1 -C 3 alkyl)-.
  • a "phenyl C 1 ⁇ C 3 alkylthio C 1 ⁇ C 3 alkyl group” unless specifically limited, (phenyl) - (C 1 ⁇ C 3 alkyl) -S- (C 1 ⁇ C 3 alkyl )-, And examples thereof include groups such as benzylthiomethyl, 1-benzylthioethyl and 2-benzylthioethyl.
  • heteroaryl C 1 -C 3 alkylthio C 1 -C 3 alkyl group means (heteroaryl)-(C 1 -C 3 ) in which the heteroaryl portion has the same meaning as described above, unless otherwise limited.
  • heteroaryl C 1 -C 3 alkylsulfinyl C 1 -C 3 alkyl group means (heteroaryl)-(C 1 -alkyl) in which the heteroaryl portion has the same meaning as described above, unless otherwise limited.
  • heteroaryl C 1 -C 3 alkylsulfonyl C 1 -C 3 alkyl group means (heteroaryl)-(C 1 -alkyl) in which the heteroaryl portion has the same meaning as described above, unless otherwise specified.
  • examples thereof include groups such as hydroxycarbonylmethyl, hydroxycarbonylethyl, and hydroxycarbonylpropyl.
  • C 1 -C 6 haloalkylthio group means a (C 1 -C 6 haloalkyl) -S— group in which the haloalkyl moiety has the above-mentioned meaning, unless otherwise specified.
  • Difluoromethylsulfinyl trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, pentafluoroethylsulfinyl, 3,3,3-trifluoropropylsulfinyl , Heptafluoropropylsulfinyl or heptafluoro-2-propylsulfinyl.
  • O)-group such as (2,2-difluoroethyl) aminocarbonyl, (2-chloro-2,2-difluoroethyl) aminocarbonyl, (2,2,2-trifluoroethyl) aminocarbonyl, Groups such as 3,3,3-trifluoropropyl) aminocarbonyl and (2,2-difluoropropyl) aminocarbonyl can be mentioned.
  • di (C 1 -C 6 haloalkyl) aminocarbonyl group means a (C 1 -C 6 haloalkyl) 2 —NC (C 1 ) wherein the haloalkyl moiety has the same meaning as described above, unless otherwise specified.
  • the two haloalkyl groups may be different from each other, for example, di (2,2-difluoroethyl) aminocarbonyl, di (2,2,2-trifluoroethyl) aminocarbonyl, N- (2,2-difluoroethyl) -N- (2,2,2-trifluoroethyl) aminocarbonyl, N- (2-chloro-2,2-difluoroethyl) -N- (2,2,2 And groups such as -trifluoroethyl) aminocarbonyl or N- (2,2,2-trifluoroethyl) -N- (2,2,2-trifluoropropyl) aminocarbonyl. .
  • the “(1,3-dioxoisoindoline-2-yl) C 1 -C 3 alkyl group” has the same meaning as the above (1,3- Represents a dioxoisoindoline-2-yl)-(C 1 -C 3 alkyl)-group, and examples thereof include a group such as (1,3-dioxoisoindoline-2-yl) methyl.
  • an agriculturally acceptable salt refers to a compound of the present invention represented by the general formula [I] or [II] in which a hydroxyl group, a carboxyl group, an amino group, or the like is present in its structure, or a pyridine ring.
  • organic bases such as triethylamine or diisopropylamine; and mineral acids such as phosphoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, boric acid, and sulfuric acid.
  • Acids include formic acid, acetic acid, lactic acid, ascorbic acid, succinic acid, fumaric acid, maleic acid, oxalic acid, Phosphate, benzoic acid, salicylic acid, tartaric acid, methanesulfonic acid, 4-toluenesulfonic acid or trifluoromethanesulfonic acid or the like.
  • the compound included in the 2,4-triazole derivative may have an E-form or a Z-form geometric isomer depending on the kind of the substituent, and the present invention relates to these E-form and Z-form. Or a mixture containing the E-form and the Z-form in any ratio.
  • 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], [II] or [III] can be produced according to the following production methods, but is not limited to these methods.
  • the compound represented by the general formula [I] “the compound represented by the formula [I]” and “the compound [I]” are synonymous.
  • the compound represented by the general formula [II-2] can be produced, for example, according to the following method.
  • X 1 represents a halogen atom
  • R 10 represents a C 1 -C 6 alkyl group or the like
  • B, R 3 , R 4 , R 5 , R 6 and n have the same meaning as described above.
  • the compound represented by the general formula [II-2] is obtained by (step 1-1) in a suitable solvent in the presence or absence of a suitable catalyst, in the presence or absence of a suitable catalyst.
  • Step 1-2 hydrolyzing the compound represented by the general formula [III-2] in a suitable solvent in the presence of a suitable acid or base It can be manufactured by the following.
  • Step 1-3 a compound represented by the general formula [III-1] is subjected to carbon monoxide insertion reaction in a suitable solvent in the presence of a suitable catalyst and a suitable base to obtain a compound of the present invention
  • Step 1-4 the compound represented by the general formula [II-1] is hydrolyzed in a suitable solvent in the presence of a suitable acid or base.
  • compound [II-2] can be produced.
  • Step 1-5) carbon monoxide insertion reaction of the compound represented by the general formula [III-1] in water or a mixed solvent of water and a suitable solvent in the presence of a suitable catalyst and a suitable base Is carried out to produce compound [II-2].
  • Step 1-1 Examples of the cyanide compound used in this reaction include sodium cyanide, potassium cyanide, ammonium cyanide, zinc cyanide, copper cyanide, and a mixture 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-1], and is preferably 1.0 to 5.0 mol.
  • Examples of the catalyst used in this reaction include tetrakis (triphenylphosphine) palladium, [1,1-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct and the like.
  • 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-1], and is preferably from 0.01 to 0.2 mol.
  • Solvents that can be used in this reaction include, for example, ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; dichloromethane , Chloroform, halogenated hydrocarbons such as 1,2-dichloroethane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, 1,3-dimethyl-2 -Aprotic polar solvents such as imidazolidinone; alcohols such as methanol, ethanol and 2-propanol; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate, butyl acetate and
  • Pentane, hexane, cyclohexane, aliphatic hydrocarbons such as heptane; pyridine, pyridine picoline, and the like; may be mentioned water or a mixed solvent thereof, or the like.
  • the amount of the solvent to be used is 0.1-500 liter, preferably 0.3-50 liter, per 1 mol of compound [III-1].
  • the reaction temperature of this reaction 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.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 10 minutes to 72 hours.
  • compound [III-2] is isolated by performing an operation such as pouring the reaction mixture into water and collecting the precipitated solid by filtration or extracting with an organic solvent and then concentrating. be able to.
  • the isolated compound [III-2] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • Step 1-2 Examples of the acid that can be used in this reaction include mineral acids such as hydrochloric acid, hydrobromic acid and sulfuric acid, carboxylic acids such as acetic acid, propionic acid and trifluoroacetic acid, and sulfonic acids such as methanesulfonic acid and trifluoromethanesulfonic acid. Can be mentioned.
  • 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-2], and is preferably 1.0 to 100.0 mol.
  • Examples of the base that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide. And inorganic bases such as alkali metal carbonates such as sodium carbonate and potassium carbonate, and alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate.
  • the amount of the base used may be appropriately selected from the range of 0.1 to 50 mol per 1 mol of the compound [III-2], and is preferably 0.5 to 20.0 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
  • 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 acetic acid and 2-propanol
  • nitriles such as acetonitrile and propionitrile
  • ketones such as acetone, methyl ethyl ketone and cyclohexanone
  • water The amount of the solvent to be used is 0.1-500 liter, preferably 0.3-30 liter
  • the reaction temperature of this reaction 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.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 10 minutes to 72 hours.
  • the reaction mixture is neutralized by pouring into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to give 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 catalyst that can be used in this reaction may be a transition metal complex or a combination of a transition metal and a ligand.
  • the transition metal complex may be tetrakis (triphenylphosphine) palladium or dichloro [1,1′- Bis (diphenylphosphino) ferrocene] palladium-dichloromethane adduct, etc .; transition metals as palladium chloride, palladium bromide, palladium acetate, etc .; and ligands as trimethylphosphine, triethylphosphine, tributylphosphine, triphenylphosphine, Examples thereof include 3-bisdimethylphosphinopropane, 1,2-bisdiphenylphosphinoethane, and 1,3-bisdiphenylphosphinopropane.
  • the amount of the catalyst to be used is 0.001-0.1 mol, preferably 0.01-0.05 mol,
  • Examples of the base that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide.
  • Inorganic bases such as alkali metal carbonates such as sodium carbonate, potassium carbonate and the like; alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; triethylamine, 4-methylmorpholine, diisopropylethylamine, 1,8- Organic bases such as diazabicyclo [5.4.0] -7-undecene, pyridine, 4-N, N-dimethylaminopyridine, 2,6-lutidine and the like can be mentioned.
  • the amount of the base to be used is 0.1 to 10 mol, preferably 0.1 to 2.0 mol, per 1 mol of compound [III-1]. However, in the case of an organic base, it can be used also as a solvent.
  • 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 N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone; methanol, ethanol Alcohols such as, 2-propanol; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl ethyl ketone and cyclohexanone; and mixed solvents thereof.
  • the amount of the solvent to be used is 0.1-500 liter, preferably 0.3
  • the reaction temperature of this reaction 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 pressure of this reaction may be selected from a range of any pressure in the range of usually from atmospheric pressure to 50 atm, preferably from 1 to less than 10 atm.
  • reaction time of this reaction varies depending on the reaction temperature, reaction pressure, reaction substrate, reaction amount and the like, but is usually 10 minutes to 72 hours.
  • 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 [II-1]. ] Can be isolated.
  • the isolated compound [II-1] can be further purified, if necessary, by column chromatography, recrystallization, or the like.
  • Step 1-4 The acid, base, solvent, reaction temperature and reaction time that can be used in this reaction are the same as in Step 1-2.
  • the reaction mixture is neutralized by pouring into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to give 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 1-5 The base, solvent, reaction temperature and reaction time that can be used in this reaction are the same as those in Step 1-3.
  • the reaction mixture is neutralized by pouring into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to give 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-1] can be produced, for example, according to the following method.
  • the compound represented by the general formula [I-1] can be obtained by converting the compound [II-2] into an acid halide or a mixed solvent in a suitable solvent in the presence or absence of a suitable catalyst.
  • the compound [IV] which is an active derivative such as an acid anhydride is converted into a compound [IV], which is then reacted with a compound [V] in a suitable solvent in the presence or absence of a suitable base.
  • the compound represented by the general formula [I-1] can be obtained by (step 2-3) compounding compound [II-2] with compound [V] in the presence or absence of a suitable condensing agent and a suitable base. It can also be produced by reacting in an appropriate solvent below.
  • Step 2-1 In order to convert the compound [II-2] to an acid halide, thionyl chloride, oxalyl chloride, phosphoryl chloride or the like 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 30 mol per 1 mol of the compound [II-2], and is preferably 0.5 to 6.0 mol. is there.
  • Examples of the catalyst that can be used in this reaction include N, N-dimethylformamide.
  • the amount of the catalyst 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 0.1 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; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; dichloromethane.
  • 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 of this reaction 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.
  • 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.
  • compound [IV] can be isolated by performing an operation such as concentration.
  • Step 2-2 The amount of compound [V] used in this reaction may be appropriately selected usually from the range of 1 to 5 mol per 1 mol of compound [IV], and is preferably 1.0 to 2.5 mol.
  • Bases that can be used in this reaction 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; hydroxides of alkali metals such as lithium hydroxide, sodium hydroxide and potassium hydroxide; hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide And alkali metal carbonates such as sodium carbonate and potassium carbonate; and inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate.
  • the amount of the base used may be appropriately selected from the range of 1 to 5 mol per 1 mol of the compound [IV], and is preferably 1.0 to 3.5 mol.
  • Solvents that can be used in this reaction include, for example, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; benzene, toluene, xylene, chlorobenzene and the like.
  • halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane
  • benzene toluene
  • xylene chlorobenzene and the like.
  • Aromatic hydrocarbons such as ethyl acetate, butyl acetate and ethyl propionate; nitriles such as acetate nitrile and propionitrile; N, N-dimethylformamide, N, N-dimethylacetamide, N- Aprotic polar solvents such as methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone; diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane D Ethers and the like; may be mentioned water or a mixed solvent thereof, or the like.
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-50 liters, per 1 mol of compound [IV].
  • This reaction can be carried out in the presence of a catalyst if necessary.
  • the catalyst include tetrabutylammonium bromide, tetrabutylammonium chloride, 15-crown-5, 18-crown-6, 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 [IV], and is preferably 0.01 to 0.1 mol.
  • 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 80 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 1 minute to 48 hours.
  • the compound [I-1] is isolated by performing operations such as pouring the reaction mixture into water, and collecting the precipitated solid by filtration or extraction and concentration with an organic solvent. be able to.
  • the isolated compound [I-1] can be further purified by column chromatography, recrystallization, and the like, if necessary.
  • Step 2-3 The amount of compound [V] to be used in this reaction 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 2.6 mol. .
  • condensing agent examples include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, N, N′-dicyclohexylcarbodiimide , N, N'-diisopropylcarbodiimide, N, N'-carbonyldiimidazole, 4- (4,6-dimethoxy-1,3,5-triazin-2-yl) -4-methylmorpholinium chloride, 1H -Benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate, ⁇ [(1-cyano-2-ethoxy-2-oxoethylidene) amino] oxy ⁇ -4-morpholinomethylene ⁇ dimethylammonium hexafluoro Phosphate, O- (7-azabenzo
  • usable bases include, for example, triethylamine, 4-methylmorpholine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] -7-undecene, pyridine, 4-N, Organic bases such as N-dimethylaminopyridine and 2,6-lutidine are exemplified.
  • the amount of the base used may be appropriately selected from the range of 0.1 to 5 mol per 1 mol of the compound [II-2], and is preferably 0.1 to 3.0 mol.
  • Solvents that can be used in this reaction include, for example, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; ethyl acetate, butyl acetate, propionic acid Esters such as ethyl; nitriles such as acetate nitrile and propionitrile; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, 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; and mixed solvents
  • This reaction can be carried out in the presence of a catalyst if necessary, and examples of the catalyst include 4-N, N-dimethylaminopyridine.
  • the amount of the catalyst to be used may be appropriately selected from the range of 0.001 to 1 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound [II-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 80 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 1 minute to 96 hours.
  • the compound [I-1] is isolated by performing operations such as pouring the reaction mixture into water, and collecting the precipitated solid by filtration or extraction and concentration with an organic solvent. be able to.
  • the isolated compound [I-1] can be further purified by column chromatography, recrystallization, and the like, if necessary.
  • the compound represented by the general formula [I-3] can be produced, for example, according to the following method.
  • B 1 represents an oxygen atom or a sulfur atom
  • L 2 represents a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a nonafluorobutanesulfonyloxy group, a benzenesulfonyloxy group, a p-toluenesulfonyloxy group
  • the compound represented by the general formula [I-3] is obtained by converting the compound represented by the general formula [I-2] and the compound [VI] into a compound having a suitable radical in the presence or absence of a suitable base. It can be produced by reacting in a suitable solvent in the presence or absence of an initiator.
  • the amount of compound [VI] to be used in this reaction may be appropriately selected from the range of 1 to 100 mol per 1 mol of compound [I-2], and is preferably 1.0 to 3.3 mol. .
  • Examples of the base that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide.
  • alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide
  • alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide.
  • inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, metal hydrides such as sodium hydride and potassium hydride, and sodium methoxy.
  • Metal salts of alcohols such as sodium chloride, sodium ethoxide, potassium tert-butoxide or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0]
  • 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-2], and is preferably 1.0 to 2.0 mol.
  • radical initiator examples include sulfurous acid, sulfites, and sulfurous acid adducts such as Rongalite (trade name, sodium formaldehyde sulfoxylate).
  • the amount of the radical initiator used may be appropriately selected from the range of 0.01 to 5 mol per 1 mol of the compound [I-2], 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
  • 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
  • nitriles such as acetonitrile and propionitrile
  • esters such as ethyl acetate, butyl acetate and ethyl propionate
  • 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 24 hours.
  • compound [I-3] is isolated by performing an operation such as pouring the reaction mixture into water, and collecting the precipitated solid by filtration or extraction and concentration with an organic solvent. be able to.
  • the isolated compound [I-3] can be further purified, if necessary, by column chromatography, recrystallization, or the like.
  • the compound represented by the general formula [I-5] can be produced, for example, according to the following method.
  • the compound represented by the general formula [I-5] can be produced by subjecting the compound [I-4] to an oxidation reaction in a suitable solvent in the presence or absence of a suitable catalyst.
  • oxidizing agent examples include hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, oxone (OXONE, trade name of EI DuPont; 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 p of the sulfur atom of the compound represented by the general formula [I-5], but is 0.8 to 10 mol per 1 mol of the compound [I-4]. May be suitably selected from the range, preferably from 0.8 to 4.0 mol.
  • a catalyst that can be used in this reaction for example, sodium tungstate can be given.
  • the amount of the catalyst to be used may be appropriately selected from the range of 0.01 to 1.0 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound [I-4].
  • 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, 2-propanol, halogenated hydrocarbons such as dichloromethane, chloroform, 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-4].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from usually -30 ° C to the reflux temperature in the reaction system, and is preferably in the range of -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 10 minutes to 24 hours.
  • the compound [I-5] is isolated by pouring the reaction mixture into water, collecting the precipitated solid by filtration or extracting with an organic solvent and then concentrating the solid. be able to.
  • the isolated compound [I-5] 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, according to the following method.
  • R b represents a C 1 -C 6 alkyl group or a C 1 -C 6 haloalkyl group
  • R 3 , R 4 , R 6 , Ra and n have the same meaning as described above.
  • the compound represented by the general formula [I-8] is obtained by reacting the compound [I-6] with the compound [VII] in a suitable solvent (step 5-1) to obtain a compound [I-7].
  • the compound [I-7] can be produced by a hydrolysis reaction in a suitable solvent in the presence or absence of a suitable base.
  • Step 5-1 As the compound [VII] that can be used in this reaction, acetic anhydride or trifluoroacetic anhydride can be mentioned.
  • the amount of compound [VII] to be used may be selected from the range of 1 mol to 1 mol of compound [I-6] and an amount sufficient for use as a solvent, and is preferably from 1.0 to 5.0. Is a mole.
  • 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; ethyl acetate, butyl acetate and ethyl propionate; Esters; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane and the like; water or a mixed solvent thereof.
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3
  • the reaction temperature of this reaction may be selected from any 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 any reaction, but is usually 5 minutes to 24 hours.
  • the compound [I-7] 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-7] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • compound [I-7] can be used in Step 5-2 without isolation and purification.
  • Step 5-2 The base, solvent, reaction temperature and reaction time that can be used in this reaction are the same as in Step 1-2 of Production Method 1.
  • 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 [I-8]. ] Can be isolated.
  • the isolated compound [I-8] can be further purified, if necessary, by column chromatography, recrystallization, or the like.
  • the compound represented by the general formula [I-9] can be produced, for example, by using the compound represented by the general formula [I-1] according to the following method.
  • sulfurizing agent examples include phosphorus pentasulfide, Lawesson's reagent (2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2). , 4-disulfide) and the like.
  • the amount of the sulfurizing agent to be used may be appropriately selected from the range of 0.5 to 30 mol per 1 mol of the compound [I-1], and is preferably 0.5 to 5.0 mol.
  • a base additive 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 used may be appropriately selected from the range of 0.01 to 10 mol per 1 mol of the compound [I-1], and is preferably 0.1 to 2.0 mol.
  • solvents examples 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 sulfoxide and sulfolane; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; water, or a mixture thereof Solvents and the like can be mentioned.
  • the amount of the solvent to be used is 0.1-300 liter, preferably 0.3-50 liter, per 1 mol of compound [I-1].
  • the reaction temperature of this reaction may be generally selected from an arbitrary temperature range from -70 ° 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 24 hours.
  • the compound [I-9] 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-9] can be isolated by concentrating the solvent from the reaction mixture. The isolated compound [I-9] 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 the compound represented by the general formula [I-10] according to the following method.
  • the reaction mixture is neutralized by pouring into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to obtain the compound [I-11]. ] Can be isolated.
  • the isolated compound [I-11] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • the compound represented by the general formula [I-1] can be produced, for example, using the compound represented by the general formula [III-1] according to the following method.
  • the compound represented by the general formula [I-1] is prepared by converting the compound represented by the general formula [III-1] and the compound [V] into a suitable solvent in the presence of a suitable catalyst and a suitable base. It can be produced by performing a carbon monoxide insertion reaction in the inside.
  • the amount of compound [V] to be used in this reaction may be appropriately selected usually from the range of 1 to 5 mol per 1 mol of compound [III-1], and is preferably 1.0 to 3.0 mol. is there.
  • the catalyst that can be used in this reaction may be a transition metal complex or a combination of a transition metal and a ligand.
  • the transition metal complex may be tetrakis (triphenylphosphine) palladium or dichloro [1,1′- Bis (diphenylphosphino) ferrocene] palladium-dichloromethane adduct, etc., transition metals as palladium chloride, palladium bromide, palladium acetate, etc., and ligands as trimethylphosphine, triethylphosphine, tributylphosphine, triphenylphosphine, Examples thereof include 3-bisdimethylphosphinopropane, 1,2-bisdiphenylphosphinoethane, and 1,3-bisdiphenylphosphinopropane.
  • the amount of the catalyst to be used is 0.001-0.1 mol, preferably 0.01-0.05 mol, per 1 mol of compound
  • Examples of the base that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide.
  • Inorganic bases such as alkali metal carbonates such as sodium carbonate, potassium carbonate and the like; alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; triethylamine, 4-methylmorpholine, diisopropylethylamine, 1,8- Organic bases such as diazabicyclo [5.4.0] -7-undecene, pyridine, 4-N, N-dimethylaminopyridine, 2,6-lutidine and the like can be mentioned.
  • the amount of the base to be used is 0.1 to 10 mol, preferably 0.1 to 7.0 mol, per 1 mol of compound [III-1]. However, in the case of an organic base, it can be used also as a solvent.
  • 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 N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone; methanol, ethanol Alcohols such as, 2-propanol; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl ethyl ketone and cyclohexanone; and mixed solvents thereof.
  • the amount of the solvent to be used is 0.1-500 liter, preferably 0.5
  • the reaction temperature of this reaction 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 pressure of this reaction may be selected from a range of any pressure in the range of usually from atmospheric pressure to 50 atm, preferably from 1 to less than 10 atm.
  • reaction time of this reaction varies depending on the reaction temperature, reaction pressure, reaction substrate, reaction amount and the like, but is usually 10 minutes to 72 hours.
  • the reaction mixture is neutralized by pouring into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to obtain the compound [I-1]. ] Can be isolated.
  • the isolated compound [I-1] can be further purified by column chromatography, recrystallization, and the like, if necessary.
  • the compound represented by the general formula [I-12] can be produced, for example, by using the compound represented by the general formula [XXIII] and the compound represented by [XXIV] according to the following method. Can be.
  • R 11 represents a C 1 -C 6 alkyl group or a C 1 -C 6 haloalkyl group
  • R 1 , R 2 , R 3 , R 4 , R 6 , R 10 , n and X 1 have the same meaning as described above, and especially B in the general formula of the compound represented by [XXIV]. Represents a boron atom.
  • the compound represented by the general formula [I-12] can be obtained by converting the compound represented by the general formula [XXIII] and the compound [XXIV] into a suitable solvent in the presence of a suitable catalyst and a suitable base. It can be produced by performing a Suzuki Miyaura coupling reaction.
  • the amount of compound [XXIV] used in this reaction may be appropriately selected usually from the range of 1 to 5 mol per 1 mol of compound [XXIII], and is preferably 1.0 to 1.5 mol.
  • the catalyst that can be used in this reaction may be a transition metal complex or a combination of a transition metal and a ligand.
  • the transition metal complex may be tetrakis (triphenylphosphine) palladium or dichloro [1,1′- Bis (diphenylphosphino) ferrocene] palladium-dichloromethane adduct, etc .; transition metals as palladium chloride, palladium bromide, palladium acetate, etc .; and ligands as trimethylphosphine, triethylphosphine, tributylphosphine, triphenylphosphine, Examples thereof include 3-bisdimethylphosphinopropane, 1,2-bisdiphenylphosphinoethane, and 1,3-bisdiphenylphosphinopropane.
  • the amount of the catalyst to be used is 0.001-0.2 mol, preferably 0.01-0.15 mol, per 1
  • Examples of the base that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide.
  • Inorganic bases such as alkali metal carbonates such as sodium carbonate, potassium carbonate and the like; alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; triethylamine, 4-methylmorpholine, diisopropylethylamine, 1,8- Organic bases such as diazabicyclo [5.4.0] -7-undecene, pyridine, 4-N, N-dimethylaminopyridine, 2,6-lutidine and the like can be mentioned.
  • the amount of the base to be used is 0.1 to 10 mol, preferably 0.1 to 4.0 mol, per 1 mol of compound [XXIII].
  • solvents 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
  • dichloromethane, chloroform Halogenated hydrocarbons such as 1,2-dichloroethane and the like
  • alcohols such as methanol, ethanol and 2-propanol
  • nitriles such as acetonitrile and propionitrile
  • keto such as acetone, methyl ethyl ketone and cyclohexanone
  • the reaction temperature of this reaction 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.
  • reaction time of this reaction varies depending on the reaction temperature, reaction pressure, reaction substrate, reaction amount and the like, but is usually 10 minutes to 72 hours.
  • compound [I-12] 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-12] can be isolated by concentrating the solvent from the reaction mixture. The isolated compound [I-12] can be further purified by column chromatography, recrystallization, or the like, if necessary.
  • the compound represented by the general formula [I-14] can be produced, for example, using the compound represented by the general formula [I-13] according to the following method.
  • the compound represented by the general formula [I-14] is produced by hydrolyzing the compound represented by the general formula [I-13] in a suitable solvent in the presence of a suitable acid or base. be able to.
  • compound [I-14] is isolated by performing operations such as pouring the reaction mixture into water and collecting the precipitated solid by filtration or extracting with an organic solvent and then concentrating. be able to.
  • the isolated compound [I-14] can be further purified, if necessary, by column chromatography, recrystallization, or the like.
  • the compound represented by the general formula [I-17] can be produced, for example, by using the compound represented by the general formula [I-15] according to the following method.
  • R 1 , R 2 , R 3 , R 4 , R 6 , R 10 , R a and n have the same meaning as described above. .
  • the compound represented by the general formula [I-17] is reacted with a diphenylphosphate azide (DPPA) in a suitable solvent in the presence of a suitable base.
  • DPPA diphenylphosphate azide
  • the compound can be produced by adding the compound R 10 OH as a nucleophile to the isocyanate [I-16] generated as above.
  • the amount of DPPA that can be used in this reaction may be appropriately selected from the range of 1 to 5 mol per 1 mol of compound [I-15], and is preferably 1.0 to 2.5 mol.
  • Examples of a base that can be used in this reaction include organic bases such as triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, and 1,8-diazabicyclo [5.4.0] -7-undecene.
  • organic bases such as triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, and 1,8-diazabicyclo [5.4.0] -7-undecene.
  • Alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide, and alkalis such as sodium carbonate and potassium carbonate
  • Inorganic bases such as metal carbonates, alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate are exemplified.
  • the amount of the base used may be appropriately selected from the range of 1 to 5
  • Solvents usable in this reaction include, for example, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; benzene, toluene, xylene, chlorobenzene and the like.
  • halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane
  • benzene toluene
  • xylene chlorobenzene and the like.
  • Aromatic hydrocarbons ; alcohols such as methanol, ethanol and 2-propanol; 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, 1,4-dioxane; water; or a mixed solvent thereof.
  • the amount of the solvent to be used is 0.1-300 liters, preferably 0.1-100 liters, per 1 mol of compound [I-15].
  • nucleophile examples include alcohols such as methanol, ethanol, 2-propanol and tert-butyl alcohol, and water.
  • the amount of the nucleophile used may be selected from the range of 1 mole to 1 mole of compound [I-15] and an amount sufficient to be used as a solvent, and is preferably 1.0 to 100 moles. is there.
  • 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 120 ° C.
  • the reaction time of this reaction varies depending on the reaction temperature, the reaction substrate and the reaction amount, but is usually 1 minute to 48 hours.
  • the compound [I-17] 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 [I-17] can be further purified by column chromatography, recrystallization, or the like, if necessary.
  • the compound represented by the general formula [I-19] can be produced, for example, using the compound represented by the general formula [I-18] according to the following method.
  • X 3 represents a hydrogen atom, a halogen atom or a cyano group, and R 3 , R 4 , R 6 , Ra and n have the same meaning as described above.
  • the compound represented by the general formula [I-19] can be prepared by preparing a compound represented by the general formula [I-18] in an appropriate solvent in Organic @ Synthesis, Coll.
  • the diazonium salt was prepared according to the method described in Vol. 3, p. 195 (1955) (for example, by a method using a mineral acid such as hydrochloric acid, sulfuric acid and hydrobromic acid and a nitrite or an alkyl nitrite). It can be produced by reacting in a suitable solvent in the presence or absence of copper halide or copper cyanide.
  • Examples of the copper halide that can be used in this reaction include copper (I) chloride, copper (I) bromide, copper (I) iodide, copper (II) chloride, copper (II) bromide, and the like.
  • the amount of the copper halide or copper cyanide to be used is 1 to 5 mol, preferably 1.0 to 2.5 mol, per 1 mol of compound [I-18].
  • 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, and 1,3-dimethyl-2-imidazolidinone; mineral acids such as hydrochloric acid and sulfuric acid; carboxylic acids such as acetic acid; water or a mixed solvent thereof.
  • the reaction temperature of this reaction may be selected from any temperature range from -70 ° C to the reflux temperature in the reaction system, and is preferably in the range of -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 10 minutes to 24 hours.
  • 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-19].
  • 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-20] can be produced, for example, by using the compound represented by the general formula [I-13] according to the following method.
  • the compound represented by the general formula [I-22] can be produced, for example, according to the following method.
  • B 2 represents an oxygen atom, a sulfur atom, a group —N (—R 7 ) —, and L 2 , R 3 , R 4 , R 5 , R 6 , R 7 , Re and n are as defined above. Means the same.
  • the compound represented by the general formula [1-22] can be obtained by converting the compound [I-20] into a compound [I-21] in a suitable solvent in the presence or absence of a suitable base (step 14-1). ] (Step 14-2) by reacting with compound [XXVII] in a suitable solvent in the presence or absence of a suitable base. Further, the compound represented by the general formula [1-22] is produced by reacting the compound [I-20] with the compound [XXVII] in a suitable solvent in the presence of azodicarboxylic acid diester and triphenylphosphine. You can also.
  • Step 14-1 The compound represented by the general formula [I-21] is obtained by reacting the compound represented by the general formula [I-20] with a halogenating reagent or a halogenating reagent in an appropriate solvent in the presence of triphenylphosphine. It can be manufactured by the following.
  • halogenating reagent used in this reaction examples include thionyl chloride, chlorine, sulfuryl chloride, carbon tetrachloride, N-chlorosuccinimide, bromine, carbon tetrabromide, 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 a molar amount corresponding to the amount of the solvent per 1 mol of the compound [I-20], and is preferably 1.0 to 100 mol.
  • the amount of triphenylphosphine used in this reaction may be appropriately selected from the range of 1 to 5 mol per 1 mol of compound [I-20], and is preferably 1.0 to 2.5 mol. .
  • the compound represented by the general formula [I-21] can be produced by reacting the compound represented by the general formula [I-20] in an appropriate solvent in the presence of a pseudohalogenating reagent. it can.
  • Examples of the pseudohalogenating reagent used in this reaction include trifluoromethanesulfonic anhydride, trifluoromethanesulfonyl chloride, p-toluenesulfonyl chloride and the like.
  • the amount of the pseudohalogenating reagent to be used may be appropriately selected from the range of 0.5 to 10 mol, preferably 0.5 to 5.0 mol, per 1 mol of compound [I-20].
  • usable bases include, for example, hydroxides of alkali metals such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metals such as calcium hydroxide and magnesium hydroxide.
  • metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide or triethylamine, 4-methylmorpholine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] -7-undecene , Pyridine, 4-N, N-dimethylaminopyridine, 2, - an organic base such as lutidine, and the like.
  • the amount of the base used may be appropriately selected from the range of 0.1 to 20 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; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; dichloromethane.
  • the amount of the solvent to be used is 0.1-100 liters, preferably 0.3-10 liters, per 1 mol of compound [I-20].
  • the reaction temperature of this reaction 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.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 10 minutes to 48 hours.
  • compound [I-21] 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-21] can be further purified, if necessary, by column chromatography, recrystallization, or the like.
  • Step 14-2 The amount of compound [XXVII] to be used in this reaction may be appropriately selected from the range of 1 to 5 mol per 1 mol of compound [I-21], and is preferably 1.0 to 2.5 mol. .
  • Examples of the base that can be used in the reaction include hydroxides of alkali metals such as lithium hydroxide, sodium hydroxide and potassium 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 Metal salts of alcohols such as sodium, sodium ethoxide, potassium tert-butoxide or triethylamine, 4-methylmorpholine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] -7-undecene, pyridine, 4-N Such as N, N-dimethylaminopyridine and 2,6-lutidine Based compounds, and the like.
  • the amount of the base to be used may be appropriately selected from the range of 1 to 5 mol per 1
  • Solvents usable in this reaction include, for example, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; benzene, toluene, xylene, chlorobenzene and the like.
  • halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane
  • benzene toluene
  • xylene chlorobenzene and the like.
  • Aromatic hydrocarbons ; alcohols such as methanol, ethanol and 2-propanol; 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, 1,4-dioxane; water; or a mixed solvent thereof.
  • the amount of the solvent to be used is 0.1-300 liters, preferably 0.1-100 liters, per 1 mol of compound [I-21].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from usually ⁇ 30 ° C. to the reflux temperature in the reaction system, and is preferably in the range of 0 ° C. to 120 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 10 minutes to 48 hours.
  • compound [I-22] 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-22] can be further purified, if necessary, by column chromatography, recrystallization, or the like.
  • Step 14-3 Examples of the azodicarboxylic acid diester that can be used in this reaction include diethyl azodicarboxylate and diisopropyl azodicarboxylate.
  • the amount of the azodicarboxylic acid diester to be used may be appropriately selected from the range of 1 to 10 mol per 1 mol of the compound [I-20], and is preferably 1.0 to 5.0 mol.
  • the amount of triphenylphosphine that can be used in this reaction 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 amount of compound [XXVII] to be used in this reaction 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. .
  • Solvents usable in this reaction include, for example, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; benzene, toluene, xylene, chlorobenzene and the like.
  • halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane
  • benzene toluene
  • xylene chlorobenzene and the like.
  • Aromatic hydrocarbons such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like Polar solvents; ethers 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 0.1-300 liters, preferably 0.1-100 liters, per 1 mol of compound [I-20].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from usually ⁇ 30 ° C. to the reflux temperature in the reaction system, and is preferably in the range of 0 ° C. to 120 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount and the like, but is usually 10 minutes to 48 hours.
  • compound [I-22] 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-22] can be further purified, if necessary, by column chromatography, recrystallization, or the like.
  • the compound represented by the general formula [I-23] can be produced, for example, according to the following method.
  • the compound represented by the general formula [I-23] can be obtained by converting the compound represented by the general formula [I-20] and the compound [VI] into a suitable solvent in the presence or absence of a suitable base. Can be produced by reacting in a solution.
  • the reaction mixture is neutralized by pouring the reaction mixture into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to obtain the compound [I-23]. ] Can be isolated.
  • the isolated compound [I-23] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • the compound represented by the general formula [I-25] can be produced, for example, according to the following method.
  • the compound represented by the general formula [I-25] can be prepared by reacting the compound represented by the general formula [I-24] with the compound [XXVIII] in a suitable solvent in the presence of a suitable base. Can be manufactured.
  • the amount of compound [XXVIII] used in this reaction may be appropriately selected from the range of 1 to 10 mol per 1 mol of compound [I-24], and is preferably 1.0 to 3.5 mol. .
  • Examples of the base that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide.
  • alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide
  • alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide.
  • inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate, metal hydrides such as sodium hydride and potassium hydride, and sodium methoxy.
  • Metal salts of alcohols such as sodium chloride, sodium ethoxide, potassium tert-butoxide or triethylamine, N, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0]
  • organic bases such as -7-undecene.
  • the amount of the base to be used may be appropriately selected from the range of 1 to 5 mol per 1 mol of compound [I-24], and is preferably 1.0 to 3.0 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
  • 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
  • nitriles such as acetonitrile and propionitrile
  • esters such as ethyl acetate, butyl acetate and ethyl propionate
  • 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 24 hours.
  • the compound [I-25] is isolated by performing operations such as pouring the reaction mixture into water, collecting the precipitated solid by filtration or extracting the solid with an organic solvent and then concentrating the solid. be able to.
  • the isolated compound [I-25] can be further purified, if necessary, by column chromatography, recrystallization, or the like.
  • the compound [III] or the like which is a production intermediate of the compound of the present invention represented by the general formula [I] or [II]
  • R C represents a cyano group or a carboxyl group
  • R 3 , R 4 , X 1 and n have the same meaning as described above.
  • the compound represented by the general formula [IX] can be produced by reacting the compound [VIII] 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 per 1 mol of the compound [VIII], and is preferably 0.5 to 2.0 mol.
  • 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 and propionitrile Nitriles; 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 [VIII].
  • the reaction temperature of this reaction may be generally 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 10 minutes to 24 hours.
  • compound [IX] can be isolated by performing an operation such as pouring the reaction mixture into water and collecting the precipitated solid by filtration or extraction with an organic solvent and then concentration. it can.
  • the isolated compound [IX] can be further purified by column chromatography, recrystallization, and the like, if necessary.
  • X 2 represents a hydrogen atom or a halogen atom
  • B 1 , R 3 , R 4 , R 6 and n have the same meaning as described above.
  • Compound [X] is converted to Compound [XI] using an acid halogenating agent in the presence or absence of a suitable catalyst, and then (Step 2′-2) The presence of a suitable base in a suitable solvent After reacting compound [XI] with compound [XII] in the presence or absence of compound [XIII], (Step 2′-3) in a suitable solvent or without a solvent, in the presence of a suitable acid, The compound [XIII] is reacted with a cyanate or thiocyanate to obtain a compound [XIV]. (Step 2′-4) The compound [XIV] is cyclized in a suitable solvent in the presence of a suitable base. Can be produced.
  • the compound represented by the general formula [III-1] can be produced by reacting the compound [XVI] with a halogenating agent in a suitable solvent.
  • the halogenating agent used in this reaction, the solvent that can be used in this reaction, the reaction temperature and the reaction time are the same as those in Production method 1 of the intermediate.
  • the compound [III-1] 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-1] can be further purified, if necessary, by column chromatography, recrystallization and the like.
  • R 5 ′ is a C 1 -C 6 alkyl group, a C 3 -C 6 cycloalkyl group, a C 3 -C 6 cycloalkyl C 1 -C 6 alkyl group, a C 1 -C 6 haloalkyl group or a C 3 It indicates ⁇ C 6 halocycloalkyl group, R 6 'represents a C 1 ⁇ C 6 alkyl group, R d represents a C 1 ⁇ C 6 alkyl group, L 3 represents a halogen atom, R 3, R 4, X 1 and n have the same meaning as described above.)
  • the compound represented by the general formula [III-4] can be prepared by a method described in JP-A-2007-308485 or according to the method described therein (step 4′-1) in an appropriate solvent or without a solvent.
  • a compound [XVIII] is subjected to a Pinner reaction with hydrogen chloride in the presence of an alcohol to produce a hydrochloride salt of the compound [XVIII], and then (Step 4′-2) the presence of a suitable base in a suitable solvent
  • the compound [XIX] is produced by reacting the compound [XVIII] with hydrazine in the presence or absence of the compound [XIX], and (Step 4′-3) in a suitable solvent in the presence or absence of a suitable base.
  • step 4′-4 reacting compound [III-3] with compound [XXII] Let it be It can be produced compound [III-4] by. At that time, compound [III-4 '] can be produced as a by-product.
  • the compound represented by the general formula [XXIII] can be obtained by the method described in (Step 6-1) US Pat. With the compound [XXIX] to produce a compound [XXX], and then (Step 6-2) by reacting the compound [XXX] with a Sandmeyer reaction in a suitable solvent in the presence of copper halide. be able to.
  • compound [XXIII] can be isolated by performing an operation such as pouring the reaction mixture into water and collecting the precipitated solid by filtration or extracting with an organic solvent and then concentrating. it can.
  • the isolated compound [XXIII] can be further purified, if necessary, by column chromatography, recrystallization, or the like.
  • the 5- (1,2,4-triazol-5-yl) benzoic acid derivative represented by the general formula [II] of the present invention or an ester thereof is a 5- (1,2,4-triazol-5-yl) benzoic acid derivative represented by the general formula [I] of the present invention.
  • the 5-phenyl-1,2,4-triazole derivative represented by the general formula [III] of the present invention is a 5- (1,2,4-triazole derivative represented by the general formula [II] of the present invention.
  • -5-yl) a compound useful as an intermediate in producing a benzoic acid derivative or an ester thereof.
  • the pesticidal composition of the present invention comprises the 5- (1,2,4-triazol-5-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. Contained as
  • 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 effective for the 5- (1,2,4-triazol-5-yl) benzoic acid amide derivative represented by the general formula [I] of the present invention or an agriculturally acceptable salt thereof. Contains as an ingredient.
  • 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 shows 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 resin Acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol, polyoxyalkylene added acetylene diol, polyoxy
  • 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).
  • 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 5- (1,2,4-triazol-5-yl) benzoic acid amide derivative represented by the general formula [I] of the present invention or an agricultural compound thereof is used. This can be done by using an acceptable amount of the active ingredient of the 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, Can be mixed and used with mites, nematicides, synergists, fungicides, antivirals, attractants, herbicides, plant growth regulators, etc. is there.
  • 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.
  • 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 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 aviglycine
  • ancimidol ancymidol
  • abscisic acid abscisic acid, inabenfide, indoleacetic acid, indolebutyric acid c acid, uniconazole, uniconazole-P, unicozole-E, ecolist, ethiclozate, ethephon, ethephon, epocholeone, oxine-sulfate, oxone-sulphate, oxine-sulphate, and oxine-sulfate carbone), calcium formate (calc
  • 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 of the trifoliate family, such as Agrotis ⁇ igas, Agrotis ggigas, and Agrotis ⁇ gigas um), Tamanagin'uwaba (Autographa nigrisigna), cotton bollworm (Helicoverpa armigera), corn earworm (Helicoverp
  • 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.
  • High-resolution mass spectroscopy (HRMS) was measured using Q Exactive Focus Hybrid Hybrid-Orbitrap LC-MS / MS System (ESI, positive mode) manufactured by Thermo Fisher Scientific.
  • A-0008 of the present invention 4-Fluoro-2-methyl-5- [1-methyl-3- (trifluoromethyl) -1H-1,2,4- [Triazol-5-yl] benzoic acid 1.00 g (3.30 mmol), oxalyl chloride 0.54 g (4.3 mmol), a few drops of N, N-dimethylformamide and 3.3 mL of chloroform were stirred at room temperature for 2 hours. After stirring, the mixture was concentrated under reduced pressure.
  • the obtained concentrate was added to 3.3 mL of a chloroform solution of 0.23 g (4.0 mmol) of cyclopropylamine and 0.40 g (3.95 mmol) of triethylamine under ice cooling, and the mixture was stirred at room temperature overnight. 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, and the obtained residue was washed with n-hexane to obtain 0.99 g (yield: 88%) of the desired product.
  • reaction solution was poured into ice water and extracted with ethyl acetate.
  • organic layer was washed with a sodium thiosulfate solution and 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.
  • F-0215 of the present invention 4-Fluoro-2-methyl-5- [1-methyl-3- (methylsulfinyl) -1H-1,2,4-triazole-
  • a 200 mL chloroform solution of 13.4 g (43.0 mmol) of methyl 5-yl] benzoate was added 45.2 g (215.2 mmol) of trifluoroacetic anhydride, and the mixture was stirred at room temperature for 2 hours and further heated at 50 ° C. for 2 hours. Stirred. After cooling at room temperature, the solvent was distilled off under reduced pressure to obtain a crude target product. This was used for the next step without purification.
  • the organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, water and saturated saline, and dried over anhydrous magnesium sulfate.
  • reaction mixture was concentrated under reduced pressure, 13 mL of a saturated aqueous solution of sodium hydrogen carbonate was added, and the mixture was stirred under heating and reflux for 3 hours. After cooling at room temperature, 2M hydrochloric acid was added to make the reaction mixture acidic, and n-hexane was added. The precipitated solid was filtered, washed with water and diisopropyl ether, and dried to obtain 3.53 g (yield: 85%) of a crude target product.
  • Example 8 4-fluoro-2-methyl-5- ⁇ 1-methyl-3-[(2,2,2-trifluoroethyl) thio] -1H-1,2,4-triazol-5-yl ⁇ -N- ( Production of 2,2,2-trifluoroethyl) benzthioamide (Compound No. B-0489 of the present invention)
  • F-0662 of the present invention 5- ⁇ 3-[(tert-butoxycarbonyl) amino] -1-methyl-1H-1,2,4-triazol-5-yl ⁇ -4-fluoro
  • 0.98 g (2.7 mmol) of methyl-2-methylbenzoate, 0.76 g (5.4 mmol) of methyl iodide and 10.8 mL of N, N-dimethylformamide was added 0.12 g of sodium hydride at room temperature ( 3.0 mmol, assuming a purity of 60%), and the mixture was stirred at the same temperature for 3 hours.
  • D-0011 of the present invention 5- ⁇ 3-[(tert-butoxycarbonyl) (methyl) amino] -1-methyl-1H-1,2
  • 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide was added.
  • A-0415 of the present invention 5- ⁇ 3-[(benzyloxy) methyl] -1-methyl-1H-1,2,4-triazol-5-yl
  • 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. Then, 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 equation (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.
  • the comparative compound Ibh-8 (described in WO 2015/150442) showed no activity at a concentration of 50 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.
  • the comparative compound Ibh-8 (described in International Publication WO 2015/150442) did not show any activity at a concentration of 50 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.
  • the comparative compound Ibh-8 (described in International Publication WO 2015/150442) did not show activity at a concentration of 10 ppm.
  • the present invention provides a novel compound having an excellent insecticidal activity and an intermediate for producing the same, and is useful in the fields of agrochemicals and agriculture, and has industrial applicability.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
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Abstract

La présente invention concerne un dérivé d'amide d'acide 5-(1,2,4-triazol-5-yl) benzoïque ayant un effet supérieur de lutte contre les organismes nuisibles ou un sel de celui-ci, un agent de lutte contre les organismes nuisibles et un intermédiaire de fabrication comprenant celui-ci en tant que composant actif. L'invention concerne un dérivé d'amide d'acide 5-(1,2,4-triazole-5-yl) benzoïque représenté par la formule générale [I] ou un sel de celui-ci, et un agent de lutte contre les organismes nuisibles caractérisé en ce qu'il comprend celui-ci en tant que composant actif (dans la formule, R1 représente un atome d'hydrogène, un groupe alkyle en C1-C6, un groupe cycloalkyle en C3-C6, ou similaire, R2 représente un atome d'hydrogène ou similaire, A représente un atome d'oxygène ou un atome de soufre, B représente une liaison simple, le groupe -O-, ou similaire, n représente un nombre entier de 0, 1, 2 ou 3, m représente un nombre entier de 0, 1 ou 2, R3 représente un atome d'halogène, un groupe alkyle en C1-C6, ou similaire, R4 représente un atome d'halogène, un groupe cyano, ou similaire, R5 représente un groupe alkyle en C1-C6, un groupe cycloalkyle en C3-C6, ou similaire, et R6 représente un atome d'hydrogène ou un groupe alkyle en C1-C6).
PCT/JP2019/031564 2018-08-17 2019-08-09 Dérivé d'amide d'acide 5-(1,2,4-triazole-5-yl) benzoïque et agent de lutte contre les organismes nuisibles WO2020036134A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021175822A1 (fr) 2020-03-02 2021-09-10 Syngenta Crop Protection Ag Composés amides d'acide benzoïque substitués par amidine pesticides

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021175822A1 (fr) 2020-03-02 2021-09-10 Syngenta Crop Protection Ag Composés amides d'acide benzoïque substitués par amidine pesticides

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