TW202019888A - 5-(1,2,4-triazol-5-yl) benzoic acid amide derivative and noxious organism control agent - Google Patents

Abstract

The present invention provides a 5-(1,2,4-triazol-5-yl) benzoic acid amide derivative or a salt thereof having an excellent noxious organism control effect, and a noxious organism control agent and a production intermediate containing it as an active ingredient. Provided is a 5-(1,2,4-triazol-5-yl) benzoic acid amide derivative represented by the general formula [I] or a salt thereof, and a noxious organism control agent characterized by containing it as an active ingredient. [In the formula, R1 represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group or the like; R2 represents a hydrogen atom or the like; A represents an oxygen atom or a sulfur atom; B represents a single bond, a group -O-or the like; n represents an integer of 0, 1, 2, or 3; m represents an integer of 0, 1, or 2; R3 represents a halogen atom, a C1-C6 alkyl group or the like; R4 represents a halogen atom, a cyano group or the like; R5 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group or the like; R6 represents a hydrogen atom or a C1-C6 alkyl group.].

Description

5-(1,2,4-triazol-5-yl)benzamide derivatives and pest control agents

The present invention relates to a novel 5-(1,2,4-triazol-5-yl)benzamide derivative or its agriculturally acceptable salt, and pest control containing the derivative as an active ingredient Agent and manufacturing intermediates.

Patent documents 1, 2, 3, and 4 disclose 5-(1,2,4-triazol-5-yl)benzamide derivatives that control the synthesis of fatty acids. However, in patent documents 1, 2, 3 The compounds described in 4 and 4 are limited so that the amine portion of the amide bond is 1-[4-(substituted phenyl) piperidinyl] group. Furthermore, there is no record of the effects of pest control.

Patent documents 5 and 6 describe 5-(1,2,4-triazol-5-yl)benzamide derivatives that control the synthesis of fatty acids, but the compounds described in patent documents 5 and 6 are limited to amides The amine part of the amine bond is 1-[3-(substituted phenyl)azetidinyl]yl or 1-[4-(substituted phenyl)piperidinyl]yl. Furthermore, there is no record of the effects of pest control.

Patent Documents 7 and 8 describe 5-(1,2,4-triazol-5-yl)benzamide derivatives having pest control effects, but the compounds described in Patent Documents 7 and 8 are Derivatives defined as substituted with 1-methyl-3-pentafluoroethyl-4-trifluoromethylpyrazol-5-yl at position 3 of the triazole ring Thing.

However, in Patent Documents 1, 2, 3, 4, 5, and 6, there is no amine moiety related to an amide bond having a 1-[3-(substituted phenyl)azetidinyl] group or 1-[4 -Description of derivatives of substituents other than (substituted phenyl) piperidinyl] group. In addition, the 1st position of the triazole ring is limited to no substitution, and there is no description about the alkyl substituent at the 1st position. On the other hand, in Patent Documents 7 and 8, the 3-position of the triazole ring is 1-methyl-3-pentafluoroethyl-4-trifluoromethylpyrazol-5-yl, and there is no equivalent The position of R ⁴ of the compound [I] of the invention is described as a substituent other than the combination of chlorine atoms, and there is no 5-(1,2,4-triazol-5-yl) benzoyl compound of the compound of the invention Description of amine derivatives.

[Prior Technical Literature] [Patent Literature]

[Patent Document 1] International Publication No. 2012/122391

[Patent Document 2] International Publication No. 2016/025816

[Patent Document 3] International Publication No. 2016/149271

[Patent Document 4] US Publication No. 20170119786

[Patent Document 5] International Publication No. 2014/008197

[Patent Document 6] International Publication No. 2015/095767

[Patent Document 7] International Publication No. 2015/150442

[Patent Document 8] International Publication No. 2017/012970

The pest control agent used for useful crops is desirably an agent that is applied to soil, stems and leaves, and shows a sufficient pest control effect at a low dose. Furthermore, as requirements for the safety of chemical substances and environmental impact are gradually increasing, it is desired to develop safer pest control agents. In addition, in recent years, pest control agents such as insecticides and acaricides have been used for a long period of time, and pests that have acquired resistance to pest control agents have appeared. Therefore, it has become difficult to completely control pests. In addition, the use of pest control agents with high human and animal toxicity also poses a problem to the safety of the operator.

The subject of the present invention is to provide a pest control agent under such circumstances, which can solve the above-mentioned problems of the conventional pest control agent, and has excellent safety, control effect, residual effect Wait.

The present inventors synthesized various 5-(1,2,4-triazol-5-yl)benzamide derivatives for the purpose of developing a pest control agent having the above-mentioned ideal characteristics, and carried out according to their physiological activities Carefully reviewed. As a result, it was found that 5-(1,2,4-triazol-5-yl)benzamide derivatives represented by the following general formula [I] (hereinafter, also referred to as the compounds of the present invention) exhibit various harmful organisms The effect of the tabletop is further studied to complete the present invention.

That is, the present invention has the following characteristics as the gist.

(1) A 5-(1,2,4-triazol-5-yl)benzamide derivative represented by the following general formula [I] or an agriculturally acceptable salt thereof.

[Where,

n represents an integer of 0, 1, 2 or 3,

m represents an integer of 0, 1, or 2,

A represents an oxygen atom or a sulfur atom,

B represents a single bond, radical -O-, radical -S(=O) _m -or radical -N(-R ⁷ )-,

R ¹ and R ² independently represent a hydrogen atom, C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkyl, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl, C ₂ to C ₆ alkynyl, C ₂ to C ₆ alkenyl, C ₂ to C ₆ haloalkynyl, C ₂ to C ₆ haloalkenyl, C ₁ to C ₆ alkoxy, C ₁ to C ₆ haloalkoxy, C ₁ to C ₆ haloalkyl, C ₃ to C ₆ halocycloalkyl, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkyl, unsubstituted or substituent group selected via substituent group α Substituted or polysubstituted phenyl, unsubstituted or substituted by substituent group α, mono- or polysubstituted phenyl C ₁ to C ₃ alkyl, unsubstituted or selected by substituent group α Substituent monosubstituted or polysubstituted heteroaryl, unsubstituted or selected via substituent group α Monosubstituted or polysubstituted heteroaryl C ₁ to C ₃ alkyl, cyano, cyano C ₁ To C ₆ alkyl, cyano C ₃ to C ₆ cycloalkyl, C ₁ to C ₆ alkoxycarbonyl C ₃ to C ₆ cycloalkyl, hydroxy, hydroxy C ₁ to C ₆ alkyl, C ₁ to C ₆ alkoxy C ₁ to C ₆ alkyl, methyl amide, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) amine, C ₁ to C ₆ Alkylcarbonyl, C ₁ to C ₆ alkoxy C ₁ to C ₆ alkylcarbonyl, C ₃ to C ₆ cycloalkylcarbonyl, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkylcarbonyl, C ₁ To C ₆ alkoxycarbonyl, aminecarboxamide, mono(C ₁ to C ₆ alkyl)aminocarbonyl, di(C ₁ to C ₆ alkyl)aminocarbonyl, C ₁ to C ₆ alkoxycarbonyl C ₁ to C ₆ alkylamino group, mono(C ₁ to C ₆ alkoxycarbonyl) amine group, unsubstituted or substituted group selected by substituent group α, mono- or poly-substituted phenylcarbonyl group, ( C ₁ to C ₆ alkylthio) carbonyl, (C ₁ to C ₆ alkyl) thiocarbonyl, (C ₁ to C ₆ alkoxy) thiocarbonyl, amine thiocarboxamide, mono (C ₁ to C ₆ alkyl)aminothiocarbonyl, di(C ₁ to C ₆ alkyl)aminothiocarbonyl, C ₁ to C ₆ alkylsulfonyl, C ₁ to C ₆ haloalkylsulfonyl, Sulfasulfonamide, mono(C ₁ to C ₆ alkyl)aminosulfonyl, di(C ₁ to C ₆ alkyl)aminosulfonyl, C ₁ to C ₆ alkoxycarbonyl C ₁ to C ₆ alkyl, aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₃ to C ₆ cycloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ haloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, di (C ₁ to C ₆ alkyl) aminocarbonyl C ₁ to C ₆ alkyl , C ₁ to C ₆ alkylcarbonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylcarbonyl C ₁ to C ₆ alkyl, hydroxyimino, C ₁ to C ₆ alkoxyimino , Hydroxyimino group C ₁ to C ₆ alkyl, C ₁ to C ₆ alkoxyimino C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkoxy imino C ₁ to C ₆ alkyl, heterocycloalkyl , Or heterocycloalkyl C ₁ to C ₆ alkyl, and R ¹ and R ² may also form a 3 to 8 membered heterocyclic ring together with these bonded nitrogen atoms, or have 1 to 4 choices A heterocyclic ring of 3 to 8 members from a heteroatom of an oxygen atom, a sulfur atom and a nitrogen atom, the heterocyclic ring may also be halogenated, cyano, nitro, C ₁ to C ₆ alkyl, C ₁ to C ₆ alkyl Oxy, C ₁ to C ₆ haloalkyl or pendant oxy substitution,

R ³ represents a halogen atom, cyano group, C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkyl group, hydroxyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ alkylthio group, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ alkylsulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) amine, amine Formyl or thiocarbamoyl,

R ⁴ represents a halogen atom, cyano group, nitro group, C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkoxy group C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkylthio group C ₁ to C ₆ Alkyl, cyano C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkyl, C ₃ to C ₆ cycloalkyl, C ₃ to C ₆ halocycloalkyl, C ₂ to C ₆ alkenyl, C ₂ to C ₆ haloalkenyl, C ₂ to C ₆ alkynyl, C ₂ to C ₆ haloalkynyl, hydroxy, C ₁ to C ₆ alkoxy, C ₁ to C ₆ haloalkoxy, C ₁ to C ₆ alkylthio, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ haloalkylthio, C ₁ to C ₆ haloalkylsulfinyl Acyl, C ₁ to C ₆ haloalkyl sulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) amine, amine formyl or amine Thiomethyl,

R ⁵ represents a hydrogen atom, halogen atom, cyano group, C ₁ to C ₆ alkyl group, C ₃ to C ₆ cycloalkyl group, C ₃ to C ₆ cycloalkyl group C ₁ to C ₆ alkyl group, C ₂ to C ₆ Alkenyl, C ₃ to C ₆ cycloalkyl C ₂ to C ₆ alkenyl, C ₂ to C ₆ alkynyl, C ₃ to C ₆ cycloalkyl C ₂ to C ₆ alkynyl, C ₁ to C ₆ haloalkane Group, C ₃ to C ₆ halocycloalkyl, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkyl, C ₂ to C ₆ haloalkenyl, C ₂ to C ₆ haloalkynyl, hydroxyl, amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkylcarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ haloalkylcarbonyl) amine C ₁ to C ₆ alkyl Group, mono (C ₃ to C ₆ cycloalkylcarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkoxycarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ To C ₆ alkyl)aminocarbonylamino C ₁ to C ₆ alkyl, di(C ₁ to C ₆ alkyl)aminocarbonylamino C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkyl) Sulfosulfonyl)amino C ₁ to C ₆ alkyl, mono(C ₁ to C ₆ haloalkylsulfonyl) amino C ₁ to C ₆ alkyl, N-(C ₁ to C ₆ alkylsulfonate Acyl)-N-(C ₁ to C ₆ alkyl)amine C ₁ to C ₆ alkyl, N-(C ₁ to C ₆ haloalkylsulfonyl)-N-(C ₁ to C ₆ alkyl Group) amine group C ₁ to C ₆ alkyl, hydroxy C ₁ to C ₆ alkyl, C ₁ to C ₆ alkoxy C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkoxy C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkoxy C ₁ to C ₆ haloalkyl, C ₃ to C ₆ cycloalkoxy C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkoxy C ₁ to C ₆ alkyl groups, unsubstituted or mono- or poly-substituted phenyl substituted by substituent group α, unsubstituted or mono- or poly-substituted substituents selected by substituent group α Heteroaryl, unsubstituted or substituted by substituent group α mono- or polysubstituted phenyl C ₁ to C ₃ alkyl, unsubstituted or substituted by substituent group α mono-substituted Or polysubstituted phenyl C ₁ to C ₃ haloalkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroaryl C ₁ to C ₃ alkyl, unsubstituted or The substituents selected through the substituent group α are mono- or polysubstituted heteroaryl C ₁ to C ₃ haloalkyl, cyano C ₁ to C ₆ alkyl, unsubstituted or selected through the substituent group α Substituted mono- or poly-substituted phenoxy C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or poly-substituted heteroaryloxy C ₁ to C ₃ alkyl Phenyl, unsubstituted or selected via substituent group α, mono- or polysubstituted phenyl C ₁ to C 3 alkoxy C ₁ to C 3 alkyl, unsubstituted or selected via substituent group α Substituent Mono- or poly-substituted heteroaryl C ₁ to C 3 alkoxy C ₁ to C 3 alkyl, mercapto C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylthio C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfinyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylthio C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylsulfinyl C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylsulfonyl C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkane Alkylthio C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkylsulfinyl C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkylsulfonyl C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylthio C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylsulfinyl C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylsulfonate Acyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfonyloxy C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylcarbonylthio C ₁ to C ₃ alkyl, unsubstituted Phenylthio C ₁ to C3 alkyl substituted by the substituent selected by the substituent group α, unsubstituted or substituted by the substituent selected by the substituent group α Sulfenyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or poly-substituted phenylsulfonyl C ₁ to C ₃ alkyl, unsubstituted or Heteroarylthio C ₁ to C3 alkyl substituted by substituents selected through substituent group α, unsubstituted or substituted monosubstituted or polysubstituted heteroaromatic groups selected through substituent group α Sulfonyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroarylsulfonyl C ₁ to C ₃ alkyl, unsubstituted Or mono- or poly-substituted phenyl C ₁ to C ₃ alkylthio C ₁ to C ₃ alkyl, unsubstituted or selected by substituent group α Substituted or polysubstituted phenyl C ₁ to C ₃ alkylsulfinyl C ₁ to C ₃ alkyl, unsubstituted or substituted by substituent group α, mono- or poly-substituted phenyl C ₁ To C ₃ alkylsulfonyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or multi-substituted heteroaryl C ₁ to C ₃ alkylthio C ₁ To C3 alkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroaryl C ₁ to C ₃ alkylsulfinyl C ₁ to C ₃ alkyl, unsubstituted Or a mono- or poly-substituted heteroaryl C ₁ to C ₃ alkylsulfonyl C ₁ to C ₃ alkyl, heterocycloalkyl C ₁ to C ₆ alkyl selected from the substituents selected through the substituent group α, C ₁ to C ₆ alkylcarbonyl C ₁ to C ₆ alkyl, unsubstituted or substituted by a substituent group α, mono- or polysubstituted phenylcarbonyl C ₁ to C ₃ alkyl, Heteroarylcarbonyl C ₁ to C ₃ alkyl, hydroxycarbonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkoxy, unsubstituted or selected via substituent group α Carbonyl C ₁ to C ₃ alkyl, mono (C ₁ to C ₆ alkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ haloalkyl) aminocarbonyl C ₁ to C ₆ alkyl Group, mono (C ₃ to C ₆ cycloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₃ to C ₆ halocycloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, di (C ₁ to C ₆ alkyl) aminocarbonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylcarbonyloxy C ₁ to C ₃ alkyl, C ₁ to C ₆ haloalkylcarbonyloxy C ₁ to C ₃ alkyl, nitro, amine, carboxamide, C ₁ to C ₆ alkylcarbonyl, carboxy, C ₁ to C ₆ alkoxycarbonyl, amine carboxamide, mono (C ₁ to C ₆ alkyl )Aminocarbonyl, mono(C ₁ to C ₆ haloalkyl)aminocarbonyl, di(C ₁ to C ₆ alkyl)aminocarbonyl, di(C ₁ to C ₆ haloalkyl)aminocarbonyl, or (1,3-bi- pendant isoindoline-2-yl) C ₁ to C ₃ alkyl, in addition, R ⁵ and R ⁷ can also form 3 to 3 together with these bonded nitrogen atoms 6-membered heterocyclic ring, or 3 to 6-membered heterocyclic ring having 1 to 4 heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom,

R ⁶ represents a hydrogen atom or a C ₁ to C ₆ alkyl group,

R ⁷ represents a hydrogen atom, C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkyl, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl, C ₂ to C ₆ alkenyl, C ₂ to C ₆ alkynyl, methyl acetyl, C ₁ to C ₆ alkylcarbonyl, C ₁ to C ₆ alkoxycarbonyl, C ₁ to C ₆ alkylsulfonyl or C ₁ to C ₆ haloalkylsulfonyl ,

Substituent group α represents a halogen atom, C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkyl group, hydroxyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ haloalkoxy group, nitro group, Cyano, mercapto, C ₁ to C ₆ alkylthio, C ₁ to C ₆ haloalkylthio, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ haloalkylsulfinyl , C ₁ to C ₆ alkylsulfonyl, C ₁ to C ₆ haloalkylsulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) Amino, mono (C ₁ to C ₆ alkylsulfonyl) amine, mono (C ₁ to C ₆ haloalkylsulfonyl) amine, N-(C ₁ to C ₆ alkylsulfonyl) -N-(C ₁ to C ₆ alkyl)amino, N-(C ₁ to C ₆ haloalkylsulfonyl)-N-(C ₁ to C ₆ alkyl)amino, carboxamide, carboxyl , C ₁ to C ₆ alkylcarbonyl, C ₁ to C ₆ alkoxycarbonyl.

(2) A pesticide composition containing the 5-(1,2,4-triazol-5-yl)benzamide derivative described in (1) or its agriculturally acceptable Salt as an active ingredient.

(3) The pesticide composition as described in (2) above, which further contains a surfactant.

(4) A pest control agent containing the 5-(1,2,4-triazol-5-yl)benzamide derivative described in (1) or its agricultural application Tolerable salts are used as active ingredients.

(5) The pest control agent as described in (4) above, wherein the pest control agent is an insecticide, nematicide and acaricide.

(6) The pest control agent as described in (5) above, which is suitable for paddy fields, dry fields, grasslands, orchards, non-agricultural land, greenhouses, nursery facilities, or plant factories in which agricultural and horticultural plants are cultivated. The pests in it have the control effect.

(7) The pest control agent according to (6), wherein the agricultural and horticultural plant is a plant imparted with resistance by breeding methods or gene recombination technology.

(8) A pest control method using the method described in (1) above Amount of active ingredient of 5-(1,2,4-triazol-5-yl)benzamide derivative or its agriculturally acceptable salt.

(9) A method for controlling harmful organisms, which comprises the 5-(1,2,4-triazol-5-yl)benzamide derivative described in (1) above or containing it in agriculture The permissible salt as an active ingredient of the pesticide composition is applied simultaneously or in batches to the agricultural or horticultural use or the place where the agricultural or horticultural use is to be cultivated or being cultivated.

(10) The pest control method as described in (8) or (9) above, wherein the place where the pest control agent is applied is a paddy field, dry field, grassland, orchard, non-agricultural land, greenhouse, nursery facility, or Plant factory.

(11) The pest control method according to any one of (8) to (10) above, wherein the 5-(1,2,4-triazole-5- Base) benzamide derivatives or their agriculturally acceptable salts are used as insecticides, nematicides and acaricides.

(12) A method for using a pest control agent using the pest control agent described in any one of (4) to (7) above for controlling pests for agricultural and horticultural use.

(13) A 5-(1,2,4-triazol-5-yl)benzoic acid derivative represented by the following general formula [II] or a salt thereof.

In the formula,

m represents an integer of 0, 1, or 2,

n represents an integer of 0, 1, 2 or 3,

B represents a single bond, radical -O-, radical -S(=O) _m -or radical -N(-R ⁷ )-,

R ³ represents a halogen atom, cyano group, C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkyl group, hydroxyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ alkylthio group, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ alkylsulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) amine, amine Formyl or thiocarbamoyl,

R ⁴ represents a halogen atom, cyano group, nitro group, C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkoxy group C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkylthio group C ₁ to C ₆ Alkyl, cyano C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkyl, C ₃ to C ₆ cycloalkyl, C ₃ to C ₆ halocycloalkyl, C ₂ to C ₆ alkenyl, C ₂ to C ₆ haloalkenyl, C ₂ to C ₆ alkynyl, C ₂ to C ₆ haloalkynyl, hydroxy, C ₁ to C ₆ alkoxy, C ₁ to C ₆ haloalkoxy, C ₁ to C ₆ alkylthio, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ haloalkylthio, C ₁ to C ₆ haloalkylsulfinyl Acyl, C ₁ to C ₆ haloalkyl sulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) amine, amine formyl or amine Thiomethyl,

R ⁵ represents a hydrogen atom, halogen atom, cyano group, C ₁ to C ₆ alkyl group, C ₃ to C ₆ cycloalkyl group, C ₃ to C ₆ cycloalkyl group C ₁ to C ₆ alkyl group, C ₂ to C ₆ Alkenyl, C ₃ to C ₆ cycloalkyl C ₂ to C ₆ alkenyl, C ₂ to C ₆ alkynyl, C ₃ to C ₆ cycloalkyl C ₂ to C ₆ alkynyl, C ₁ to C ₆ haloalkane Group, C ₃ to C ₆ halocycloalkyl, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkyl, C ₂ to C ₆ haloalkenyl, C ₂ to C ₆ haloalkynyl, hydroxyl, amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkylcarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ haloalkylcarbonyl) amine C ₁ to C ₆ alkyl Group, mono (C ₃ to C ₆ cycloalkylcarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkoxycarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ To C ₆ alkyl)aminocarbonylamino C ₁ to C ₆ alkyl, di(C ₁ to C ₆ alkyl)aminocarbonylamino C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkyl) Sulfosulfonyl)amino C ₁ to C ₆ alkyl, mono(C ₁ to C ₆ haloalkylsulfonyl)amino C ₁ to C ₆ alkyl, N- (C ₁ to C ₆ alkylsulfonate) Acyl)-N-(C ₁ to C ₆ alkyl)amine C ₁ to C ₆ alkyl, N-(C ₁ to C ₆ haloalkylsulfonyl)-N-(C ₁ to C ₆ alkyl Group) amine group C ₁ to C ₆ alkyl, hydroxy C ₁ to C ₆ alkyl, C ₁ to C ₆ alkoxy C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkoxy C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkoxy C ₁ to C ₆ haloalkyl, C ₃ to C ₆ cycloalkoxy C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkoxy C ₁ to C ₆ alkyl groups, unsubstituted or mono- or poly-substituted phenyl substituted by substituent group α, unsubstituted or mono- or poly-substituted substituents selected by substituent group α Heteroaryl, unsubstituted or substituted by substituent group α mono- or polysubstituted phenyl C ₁ to C ₃ alkyl, unsubstituted or substituted by substituent group α mono-substituted Or polysubstituted phenyl C ₁ to C ₃ haloalkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroaryl C ₁ to C ₃ alkyl, unsubstituted or The substituents selected through the substituent group α are mono- or polysubstituted heteroaryl C ₁ to C ₃ haloalkyl, cyano C ₁ to C ₆ alkyl, unsubstituted or selected through the substituent group α Substituted mono- or poly-substituted phenoxy C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or poly-substituted heteroaryloxy C ₁ to C ₃ alkyl Phenyl, unsubstituted or selected via substituent group α, mono- or polysubstituted phenyl C ₁ to C 3 alkoxy C ₁ to C 3 alkyl, unsubstituted or selected via substituent group α replace Mono- or polysubstituted heteroaryl C ₁ to C 3 alkoxy C ₁ to C 3 alkyl, mercapto C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylthio C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfinyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylthio C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylsulfinyl C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylsulfonyl C ₁ to C ₆ alkyl, C ₃ to C ₆ ring Alkylthio C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkylsulfinyl C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkylsulfonyl C ₁ to C ₆ alkyl , C ₃ to C ₆ halocycloalkylthio C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylsulfinyl C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkyl Sulfonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfonyloxy C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylcarbonylthio C ₁ to C ₃ alkyl, none Substituted or selected substituents through substituent group α are mono- or multi-substituted phenylthio C ₁ to C 3 alkyl groups, unsubstituted or selected through substituent group α are mono- or poly-substituted Phenylsulfinyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted phenylsulfonyl C ₁ to C ₃ alkyl, unsubstituted Or a mono- or poly-substituted heteroarylthio C ₁ to C 3 alkyl group selected by the substituent group α, unsubstituted or a mono- or poly-substituted hetero group substituted by the substituent group α Arylsulfinyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroarylsulfonyl C ₁ to C ₃ alkyl, unsubstituted Phenyl C ₁ to C ₃ alkylthio C ₁ to C ₃ alkyl, unsubstituted or substituent selected by substituent group α Monosubstituted or polysubstituted phenyl C ₁ to C ₃ alkylsulfinyl C ₁ to C ₃ alkyl, unsubstituted or selected via substituent group α, monosubstituted or polysubstituted phenyl C ₁ to C ₃ alkylsulfonyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or poly-substituted heteroaryl C ₁ to C ₃ alkylthio C ₁ to C3 alkyl, unsubstituted or selected by substituent group α, mono- or polysubstituted heteroaryl C ₁ to C ₃ alkylsulfinyl C ₁ to C ₃ alkyl, unsubstituted Substituted or mono- or poly-substituted heteroaryl C ₁ to C ₃ alkylsulfonyl C ₁ to C ₃ alkyl, heterocycloalkyl C ₁ to C ₆ alkyl , C ₁ to C ₆ alkylcarbonyl C ₁ to C ₆ alkyl, unsubstituted or substituted by the substituent group α selected mono- or multi-substituted phenylcarbonyl C ₁ to C ₃ alkyl , Unsubstituted or selected via substituent group α, mono- or poly-substituted heteroarylcarbonyl C ₁ to C ₃ alkyl, hydroxycarbonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkoxy Alkylcarbonyl C ₁ to C ₃ alkyl, mono(C ₁ to C ₆ alkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono(C ₁ to C ₆ haloalkyl) aminocarbonyl C ₁ to C ₆ Alkyl, mono (C ₃ to C ₆ cycloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₃ to C ₆ halocycloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, di( C ₁ to C ₆ alkyl) Aminocarbonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylcarbonyloxy C ₁ to C ₃ alkyl, C ₁ to C ₆ haloalkylcarbonyloxy C ₁ To C ₃ alkyl, nitro, amine, methyl acetyl, C ₁ to C ₆ alkylcarbonyl, carboxy, C ₁ to C ₆ alkoxycarbonyl, amine methyl, mono(C ₁ to C ₆ alkyl Group) aminocarbonyl, mono(C ₁ to C ₆ haloalkyl) aminocarbonyl, di(C ₁ to C ₆ alkyl)aminocarbonyl, di(C ₁ to C ₆ haloalkyl)aminocarbonyl, Or (1,3-bi- pendant isoindoline-2-yl) C ₁ to C ₃ alkyl, and R ⁵ and R ⁷ can also form together with these bonded nitrogen atoms 3 Heterocycles up to 6 members, or heterocycles 3 to 6 members having 1 to 4 heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom,

R ⁶ and R ⁸ each independently represent a hydrogen atom or a C ₁ to C ₆ alkyl group,

R ⁷ represents a hydrogen atom, C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkyl, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl, C ₂ to C ₆ alkenyl, C ₂ to C ₆ alkynyl, methyl acetyl, C ₁ to C ₆ alkylcarbonyl, C ₁ to C ₆ alkoxycarbonyl, C ₁ to C ₆ alkylsulfonyl or C ₁ to C ₆ haloalkylsulfonyl ,

Substituent group α represents a halogen atom, C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkyl group, hydroxyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ haloalkoxy group, nitro group, Cyano, mercapto, C ₁ to C ₆ alkylthio, C ₁ to C ₆ haloalkylthio, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ haloalkylsulfinyl , C ₁ to C ₆ alkylsulfonyl, C ₁ to C ₆ haloalkylsulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) Amino, mono (C ₁ to C ₆ alkylsulfonyl) amine, mono (C ₁ to C ₆ haloalkylsulfonyl) amine, N-(C ₁ to C ₆ alkylsulfonyl) -N-(C ₁ to C ₆ alkyl)amino, N-(C ₁ to C ₆ haloalkylsulfonyl)-N-(C ₁ to C ₆ alkyl)amino, carboxamide, carboxyl , C ₁ to C ₆ alkylcarbonyl, C ₁ to C ₆ alkoxycarbonyl.

(14) A 5-phenyl-1,2,4-triazole derivative represented by the following general formula [III] or a salt thereof.

In the formula,

m represents an integer of 0, 1, or 2,

n represents an integer of 0, 1, or 2,

B represents a single bond, base-O-, base-S(=O)m- or base-N(-R ⁷ )-,

R ³ represents a halogen atom, cyano group, C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkyl group, hydroxyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ alkylthio group, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ alkylsulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) amine, amine Formyl or thiocarbamoyl,

R ⁴ represents a halogen atom, cyano group, nitro group, C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkoxy group C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkylthio group C ₁ to C ₆ Alkyl, cyano C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkyl, C ₃ to C ₆ cycloalkyl, C ₃ to C ₆ halocycloalkyl, C ₂ to C ₆ alkenyl, C ₂ to C ₆ haloalkenyl, C ₂ to C ₆ alkynyl, C ₂ to C ₆ haloalkynyl, hydroxy, C ₁ to C ₆ alkoxy, C ₁ to C ₆ haloalkoxy, C ₁ to C ₆ alkylthio, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ haloalkylthio, C ₁ to C ₆ haloalkylsulfinyl Acyl, C ₁ to C ₆ haloalkyl sulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) amine, amine formyl or amine Thiomethyl,

R ⁵ represents a hydrogen atom, halogen atom, cyano group, C ₁ to C ₆ alkyl group, C ₃ to C ₆ cycloalkyl group, C ₃ to C ₆ cycloalkyl group C ₁ to C ₆ alkyl group, C ₂ to C ₆ Alkenyl, C ₃ to C ₆ cycloalkyl C ₂ to C ₆ alkenyl, C ₂ to C ₆ alkynyl, C ₃ to C ₆ cycloalkyl C ₂ to C ₆ alkynyl, C ₁ to C ₆ haloalkane Group, C ₃ to C ₆ halocycloalkyl, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkyl, C ₂ to C ₆ haloalkenyl, C ₂ to C ₆ haloalkynyl, hydroxyl, amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkylcarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ haloalkylcarbonyl) amine C ₁ to C ₆ alkyl Group, mono (C ₃ to C ₆ cycloalkylcarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkoxycarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ To C ₆ alkyl)aminocarbonylamino C ₁ to C ₆ alkyl, di(C ₁ to C ₆ alkyl)aminocarbonylamino C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkyl) Sulfosulfonyl)amino C ₁ to C ₆ alkyl, mono(C ₁ to C ₆ haloalkylsulfonyl) amino C ₁ to C ₆ alkyl, N-(C ₁ to C ₆ alkylsulfonate Acyl)-N-(C ₁ to C ₆ alkyl)amine C ₁ to C ₆ alkyl, N-(C ₁ to C ₆ haloalkylsulfonyl)-N-(C ₁ to C ₆ alkyl Group) amine group C ₁ to C ₆ alkyl, hydroxy C ₁ to C ₆ alkyl, C ₁ to C ₆ alkoxy C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkoxy C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkoxy C ₁ to C ₆ haloalkyl, C ₃ to C ₆ cycloalkoxy C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkoxy C ₁ to C ₆ alkyl groups, unsubstituted or mono- or poly-substituted phenyl substituted by substituent group α, unsubstituted or mono- or poly-substituted substituents selected by substituent group α Heteroaryl, unsubstituted or substituted by substituent group α mono- or polysubstituted phenyl C ₁ to C ₃ alkyl, unsubstituted or substituted by substituent group α mono-substituted Or polysubstituted phenyl C ₁ to C ₃ haloalkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroaryl C ₁ to C ₃ alkyl, unsubstituted or The substituents selected through the substituent group α are mono- or polysubstituted heteroaryl C ₁ to C ₃ haloalkyl, cyano C ₁ to C ₆ alkyl, unsubstituted or selected through the substituent group α Substituted mono- or poly-substituted phenoxy C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or poly-substituted heteroaryloxy C ₁ to C ₃ alkyl Phenyl, unsubstituted or selected via substituent group α, mono- or polysubstituted phenyl C ₁ to C 3 alkoxy C ₁ to C 3 alkyl, unsubstituted or selected via substituent group α Substituent Mono- or poly-substituted heteroaryl C ₁ to C 3 alkoxy C ₁ to C 3 alkyl, mercapto C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylthio C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfinyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylthio C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylsulfinyl C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylsulfonyl C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkane Alkylthio C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkylsulfinyl C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkylsulfonyl C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylthio C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylsulfinyl C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylsulfonate Acyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfonyloxy C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylcarbonylthio C ₁ to C ₃ alkyl, unsubstituted Phenylthio C ₁ to C3 alkyl substituted by the substituent selected by the substituent group α, unsubstituted or substituted by the substituent selected by the substituent group α Sulfenyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or poly-substituted phenylsulfonyl C ₁ to C ₃ alkyl, unsubstituted or Heteroarylthio C ₁ to C3 alkyl substituted by substituents selected through substituent group α, unsubstituted or substituted monosubstituted or polysubstituted heteroaromatic groups selected through substituent group α Sulfonyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroarylsulfonyl C ₁ to C ₃ alkyl, unsubstituted Or mono- or poly-substituted phenyl C ₁ to C ₃ alkylthio C ₁ to C ₃ alkyl, unsubstituted or selected by substituent group α Substituted or polysubstituted phenyl C ₁ to C ₃ alkylsulfinyl C ₁ to C ₃ alkyl, unsubstituted or substituted by substituent group α, mono- or poly-substituted phenyl C ₁ To C ₃ alkylsulfonyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or multi-substituted heteroaryl C ₁ to C ₃ alkylthio C ₁ To C3 alkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroaryl C ₁ to C ₃ alkylsulfinyl C ₁ to C ₃ alkyl, unsubstituted Or a mono- or poly-substituted heteroaryl C ₁ to C ₃ alkylsulfonyl C ₁ to C ₃ alkyl, heterocycloalkyl C ₁ to C ₆ alkyl selected from the substituents selected through the substituent group α, C ₁ to C ₆ alkylcarbonyl C ₁ to C ₆ alkyl, unsubstituted or substituted by a substituent group α, mono- or polysubstituted phenylcarbonyl C ₁ to C ₃ alkyl, Heteroarylcarbonyl C ₁ to C ₃ alkyl, hydroxycarbonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkoxy, unsubstituted or selected via substituent group α Carbonyl C ₁ to C ₃ alkyl, mono (C ₁ to C ₆ alkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ haloalkyl) aminocarbonyl C ₁ to C ₆ alkyl Group, mono (C ₃ to C ₆ cycloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₃ to C ₆ halocycloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, di (C ₁ to C ₆ alkyl) aminocarbonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylcarbonyloxy C ₁ to C ₃ alkyl, C ₁ to C ₆ haloalkylcarbonyloxy C ₁ to C ₃ alkyl, nitro, amine, carboxamide, C ₁ to C ₆ alkylcarbonyl, carboxy, C ₁ to C ₆ alkoxycarbonyl, amine carboxamide, mono (C ₁ to C ₆ alkyl )Aminocarbonyl, mono(C ₁ to C ₆ haloalkyl)aminocarbonyl, di(C ₁ to C ₆ alkyl)aminocarbonyl, di(C ₁ to C ₆ haloalkyl)aminocarbonyl, or (1,3-bi- pendant isoindoline-2-yl) C ₁ to C ₃ alkyl, and R ⁵ and R ⁷ can also form 3 to 3 together with these bonded nitrogen atoms 6-membered heterocyclic ring, or 3 to 6-membered heterocyclic ring having 1 to 4 heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom,

R ⁶ represents a hydrogen atom or a C ₁ to C ₆ alkyl group,

R ⁷ represents a hydrogen atom, C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkyl, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl, C ₂ to C ₆ alkenyl, C ₂ to C ₆ alkynyl, methyl acetyl, C ₁ to C ₆ alkylcarbonyl, C ₁ to C ₆ alkoxycarbonyl, C ₁ to C ₆ alkylsulfonyl or C ₁ to C ₆ haloalkylsulfonyl ,

R ⁹ represents a hydrogen atom, a halogen atom or a cyano group,

Substituent group α represents a halogen atom, C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkyl group, hydroxyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ haloalkoxy group, nitro group, Cyano, mercapto, C ₁ to C ₆ alkylthio, C ₁ to C ₆ haloalkylthio, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ haloalkylsulfinyl , C ₁ to C ₆ alkylsulfonyl, C ₁ to C ₆ haloalkylsulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) Amino, mono (C ₁ to C ₆ alkylsulfonyl) amine, mono (C ₁ to C ₆ haloalkylsulfonyl) amine, N-(C ₁ to C ₆ alkylsulfonyl) -N-(C ₁ to C ₆ alkyl)amino, N-(C ₁ to C ₆ haloalkylsulfonyl)-N-(C ₁ to C ₆ alkyl)amino, carboxamide, carboxyl , C ₁ to C ₆ alkylcarbonyl, C ₁ to C ₆ alkoxycarbonyl.

The pest control agent containing the compound of the present invention is against Hemiptera pests, Lepidoptera pests, Coleoptera pests, Diptera pests, Hymenoptera pests, Orthoptera pests, Thysanoptera pests, mite pests, plant parasitic nematodes and other wide-ranging pests exhibit excellent control effects. Furthermore, pests that have acquired resistance can also be controlled.

In particular, the pest control agent containing the compound of the present invention is a spider mite represented by Tetranychus urticae Koch, Tetranychus kanzawai Kishida, Panonychus citri, etc. Hemiptera pests represented by brown planthopper (Nilaparvata lugens stal), pseudo black-tailed leafhopper (Nephotettix cincticeps), cotton aphid (Aphis gossypii Glover), etc.; represented by rice water weevils (Lissorhoptrus oryzophilus Kuschel), negative mud Coleoptera pests such as Oulema oryzae, Mimela splendens, etc.; nematodes such as Meloidogyne incognita; and Plutella xylostella, Chilo suppressalis, and Spodoptera exigua (Helicoverpa armigera) and other lepidopteran pests have shown the effect of the table. Furthermore, because of its excellent permeability and migration properties, it is possible to adopt a safe and labor-saving application method by soil treatment.

[Forms for carrying out the invention]

The symbols and terms described in this manual are explained below.

In the present invention, "harm control agent" means in the field of agriculture and horticulture, livestock And insecticides, acaricides, nematicides for pets and other animals, household or epidemic prevention.

In the present invention, "halogen atom" means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

In the present invention, “C ₁ to C ₆ ”and other symbols indicate that the carbon number of the substituent that follows is 1 to 6 at this time.

In the present invention, "C ₁ to C ₆ alkyl group" means a linear or branched alkyl group having 1 to 6 carbon atoms without particular limitation, for example, methyl, ethyl, n-propyl , Isopropyl, n-butyl, second butyl, isobutyl, third butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1- Ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methyl Amyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethyl Butyl butyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2, Groups such as 2-trimethylpropyl, 1-ethyl-1-methylpropyl, or 1-ethyl-2-methylpropyl.

In the present invention, "C ₃ to C ₆ cycloalkyl" means a cycloalkyl group having 3 to 6 carbon atoms without particular limitation, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl Equal base.

In the present invention, "C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl" means a cycloalkyl moiety and an alkyl moiety having the above meaning (C ₃ to C ₆ cycloalkyl), without particular limitation -(C ₁ to C ₆ alkyl)-yl, for example, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-(cyclopropyl)ethyl, 2- Groups such as (cyclopropyl)ethyl or 1-(cyclopropyl)propyl.

In the present invention, "C ₂ to C ₆ alkenyl group" means a straight or branched alkenyl group having 2 to 6 carbon atoms without particular limitation, and examples include vinyl, 1-propenyl, and iso Propenyl, 2-propenyl, 1-butenyl, 1-methyl-1-propenyl, 2-butenyl, 1-methyl-2-propenyl, 3-butenyl, 2-methyl -1-propenyl, 2-methyl-2-propenyl, 1,3-butadienyl, 1-pentenyl, 1-ethyl-2-propenyl, 2-pentenyl, 1-methyl 1-butenyl, 3-pentenyl, 1-methyl-2-butenyl, 4-pentenyl, 1-methyl-3-butenyl, 3-methyl-1-butenyl Alkenyl, 1,2-dimethyl-2-propenyl, 1,1-dimethyl-2-propenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl , 1,2-dimethyl-1-propenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,3-pentadienyl, 1-vinyl- 2-propenyl, 1-hexenyl, 1-propyl-2-propenyl, 2-hexenyl, 1-methyl-1-pentenyl, 1-ethyl-2-butenyl, 3 -Hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-4-pentenyl, 1-ethyl-3-butenyl, 1-(isobutyl)vinyl, 1 -Ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-2-propenyl, 1-(isopropyl)-2-propenyl, 2-methyl-2-pentan Alkenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1,3-dimethyl-2-butenyl, 1,1-dimethyl-3-butene Alkenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-3-butene Groups such as alkenyl, 1,1,2-trimethyl-2-propenyl, 1,5-hexadienyl, 1-vinyl-3-butenyl, or 2,4-hexadienyl.

In the present invention, "C ₃ to C ₆ cycloalkyl C ₂ to C ₆ alkenyl" means that the cycloalkyl portion and the alkenyl portion have the above meanings (C ₃ to C ₆ cycloalkyl) without particular limitation. -(C ₂ to C ₆ alkenyl)-yl, for example, 2-cyclopropylvinyl, 2-cyclobutylvinyl, 2-cyclopentylvinyl or 2-cyclohexylvinyl, etc.

In the present invention, "C ₂ to C ₆ alkynyl" refers to a linear or branched alkynyl group having 2 to 6 carbon atoms without particular limitation, and examples thereof include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-ethyl-2-propynyl Group, 2-pentynyl, 3-pentynyl, 1-methyl-2-butynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl Alkynyl, 1-hexynyl, 1-(n-propyl)-2-propynyl, 2-hexynyl, 1-ethyl-2-butynyl, 3-hexynyl, 1-methyl -2-pentynyl, 1-methyl-3-hexynyl, 4-methyl-1-pentynyl, 3-methyl-1-pentynyl, 5-hexynyl, 1-ethyl -3-butynyl, 1-ethyl-1-methyl-2-propynyl, 1-(isopropyl)-2-propynyl, 1,1-dimethyl-2-butynyl Or 2,2-dimethyl-3-butynyl and other groups.

In the present invention, "C ₃ to C ₆ cycloalkyl C ₂ to C ₆ alkynyl" means a cycloalkyl moiety and an alkynyl moiety expresses the above meaning without limitation (C ₃ to C ₆ cycloalkyl) The -(C ₂ to C ₆ alkynyl)-yl group includes, for example, groups such as cyclopropylethynyl, cyclobutylethynyl, cyclopentylethynyl, and cyclohexylethynyl.

In the present invention, "C ₂ to C ₆ haloalkynyl" means a straight or branched alkynyl group having 2 to 6 carbon atoms substituted with the same or different 1 to 9 halogen atoms, without particular limitation , For example, fluoroethynyl, chloroethynyl, bromoethynyl, iodoethynyl, 3-fluoro-2-propynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl , 3-iodo-2-propynyl, 4-fluoro-3-butynyl, 4-chloro-3-butynyl, 4-bromo-3-butynyl, 4-iodo-3-butynyl , 4,4-difluoro-2-butynyl, 4,4-dichloro-2-butynyl, 4,4,4-trifluoro-2-butynyl, 4,4,4-trichloro -2-butynyl, 3-fluoro-1-methyl-2-propynyl, 3-chloro-1-methyl-2-propynyl, 5-fluoro-4-pentynyl, 5-chloro -4-pentynyl, 5,5,5-trifluoro-3-pentynyl, 5,5,5-trichloro-3-pentynyl, 4-fluoro-2-methyl-3-butyn Group, 4-chloro-2-methyl-3-butynyl, 6-fluoro-5-hexynyl, 6-chloro-5-hexynyl, 6,6,6-trifluoro-4-hexyne Group, 6,6,6-trichloro-4-hexynyl, 5-fluoro-3-methyl-4-pentynyl or 5-chloro-3-methyl-4-pentynyl.

In the present invention, "C ₂ to C ₆ haloalkenyl" means a straight or branched alkenyl group having 2 to 6 carbon atoms substituted with the same or different 1 to 11 halogen atoms without particular limitation , For example: 1-fluorovinyl, 2-fluorovinyl, 1,2-difluorovinyl, 2,2-difluorovinyl, trifluorovinyl, 1-chlorovinyl, 2-chlorovinyl Group, 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-difluoro-2-propenyl, 3,3-difluoro-2-propenyl, 3,3-difluoro-1-propenyl, 2,3,3-trifluoro-2-propenyl, 3, 3,3-trifluoro-1-propenyl, 2-chloro-3,3,3-trifluoro-1-propenyl, 1,2,3,3,3-pentafluoro-1-propenyl, 1- Chloro-2-propenyl, 2-chloro-2-propenyl, 3-chloro-2-propenyl, 2,3-dichloro-2-propenyl, 3,3-dichloro-2-propenyl, 3 ,3-dichloro-1-propenyl, 2,3,3-trichloro-2-propenyl, 3,3,3-trichloro-1-propenyl, 3-bromo-2-propenyl, 3, 3-dibromo-2-propenyl, 3,3-diiodo-2-propenyl, 2,2-difluoro-1-propen-2-yl, 3,3,3-trifluoro-1-propenyl- 2-yl, 3,3,3-trichloro-1-propen-2-yl, 4-fluoro-3-butenyl, 4,4-difluoro-3-butenyl, 4,4-difluoro -3-buten-2-yl, 4,4,4-trifluoro-2-butenyl, 3,4,4-trifluoro-3-butenyl, 2-trifluoromethyl-2-propene Group, 2-trifluoromethyl-3,3-difluoro-2-propenyl, 4,4,4-trifluoro-3-chloro-2-butenyl, 4,4-dichloro-3-butene Alkenyl, 4,4,4-trichloro-2-butenyl, 2-trichloromethyl-2-propenyl, 5,5-difluoro-4-pentenyl, 4,5,5-tri Fluoro-4-pentenyl, 5,5,5-trifluoro-3-pentenyl, 4,4,4-trifluoro-3-methyl-2-butenyl, 4,4,4-triene Fluoro-3-trifluoromethyl-2-butenyl, 5,5-dichloro-4-pentenyl, 4,4,4-trichloro-3-methyl-2-butenyl, 6, 6-difluoro-5-hexenyl, 5,6,6-trifluoro-5-pentenyl, 6,6,6-trifluoro-4-pentenyl, 5,5,5-trifluoro- 4-methyl-3-pentenyl, 5,5,5-trifluoro-4-trifluoromethyl-3-pentenyl, 6,6-dichloro-5-hexenyl or 5,5, 5-trichloro-4-methyl-3-pentenyl and other groups.

In the present invention, "C ₁ to C ₆ haloalkyl" means a straight or branched alkyl group having 1 to 6 carbon atoms substituted with 1 to 13 halogen atoms of the same or different halogen atoms, without particular limitation, For example, it may mean a haloalkyl group, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, Tribromomethyl, iodomethyl, chlorodifluoromethyl, dichlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl , 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1-chloroethyl, 2-chloroethyl, 1,1-dichloroethyl , 2,2-dichloroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrachloroethyl, pentachloroethyl, 1-bromoethyl, 2-bromoethyl , 2,2,2-tribromoethyl, 1-iodoethyl, 2-iodoethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3 -Trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, heptafluoropropyl, 1-fluoropropane-2- Group, 2-fluoropropane-2-yl, 1,1-difluoropropane-2-yl, 1,2-difluoropropane-2-yl, 1,3-difluoropropane-2-yl, 1,2 ,3-trifluoropropane-2-yl, 1,1,3,3-tetrafluoropropane-2-yl, 1,1,1,3,3,3-hexafluoropropane-2-yl, heptafluoropropane-2 -Group, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 1,1-dichloropropyl, 2,2-dichloropropyl, 3,3-dichloropropyl, 3, 3,3-trichloropropyl, 2,2,3,3,3-pentachloropropyl, heptachloropropyl, 1-chloropropane-2-yl, 2-chloropropane-2-yl, 1,1 -Dichloropropane-2-yl, 1,2-dichloropropane-2-yl, 1,3-dichloropropane-2-yl, 1,2,3-trichloropropane-2-yl, 1,1 ,3,3-tetrachloropropane-2-yl, 1,1,1,3,3,3-hexachloropropane-2-yl, heptachloropropane-2-yl, 1-bromopropyl, 2-bromo Propyl, 3-bromopropyl, 1-bromopropane-2-yl, 2-bromopropane-2-yl, 1-iodopropyl, 2-iodopropyl, 3-iodopropyl, 1-iodopropane- 2-yl, 2-iodopropane-2-yl, 1-fluorobutyl, 2-fluorobutyl, 3-fluorobutyl, 4-fluorobutyl, 4,4-difluorobutyl, 4,4, 4-trifluorobutyl, 4,4,4-trifluoro-3-methylbutyl, 3,3,4,4,4-pentafluorobutyl, 2,2,3,4,4,4- Hexafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, nonafluorobutyl, 1,1,1-trifluorobutan-2-yl, 4,4,4- Trifluorobutane-2-yl, 3,3,4,4,4-pentafluorobutane-2-yl, nonafluorobutane-2-yl, 1,1,1,3,3,3-hexa Fluoro-2-(trifluoromethyl)propane- 2-yl, 1-chlorobutyl, 2-chlorobutyl, 3-chlorobutyl, 4-chlorobutyl, 4,4-dichlorobutyl, 4,4,4-trichlorobutyl, nonachloro Butyl, 1,1,1-trichlorobutan-2-yl, 4,4,4-trichlorobutan-2-yl, nonachlorobutan-2-yl, 1-bromobutyl, 2- Bromobutyl, 3-bromobutyl, 4-bromobutyl, 1-iodobutyl, 2-iodobutyl, 3-iodobutyl, 4-iodobutyl, 4-chloro-1,1,2, 2,3,3,4,4-octafluorobutyl, 4-bromo-1,1,2,2,3,3,4,4-octafluorobutyl, 1-fluoropentyl, 2-fluoropentane Group, 3-fluoropentyl, 4-fluoropentyl, 5-fluoropentyl, 5,5,5-trifluoropentyl, 4,4,5,5,5-pentafluoropentyl, 3,3, 4,4,5,5,5-heptafluoropentyl, 2,2,3,3,4,4,5,5-octafluoropentyl, 2,2,3,3,4,4,5, 5,5-nonafluoropentyl, undecafluoropentyl, 1-chloropentyl, 2-chloropentyl, 3-chloropentyl, 4-chloropentyl, 5-chloropentyl, 5,5,5 -Trichloropentyl, 4,4,5,5,5-pentachloropentyl, 3,3,4,4,5,5,5-heptachloropentyl, 2,2,3,3,4, 4,5,5,5-nonachloropentyl, undecylpentyl, 1-bromopentyl, 2-bromopentyl, 3-bromopentyl, 4-bromopentyl, 5-bromopentyl, 5 -Iodopentyl, 1-fluorohexyl, 2-fluorohexyl, 3-fluorohexyl, 4-fluorohexyl, 5-fluorohexyl, 6-fluorohexyl, 6,6,6-trifluorohexyl, 5,5,6 ,6,6-pentafluorohexyl, 4,4,5,5,6,6,6-heptafluorohexyl, 3,3,4,4,5,5,6,6,6-nonafluorohexyl, 2 ,2,3,3,4,4,5,5,6,6,6-undecylfluorohexyl, 2,2,3,3,4,4,5,5,6,6-decafluorohexyl, Tridecylfluorohexyl, 1-chlorohexyl, 2-chlorohexyl, 3-chlorohexyl, 4-chlorohexyl, 5-chlorohexyl, 6-chlorohexyl, 5-bromohexyl, 6-bromohexyl, 5-iodohexyl or 6-iodohexyl and other groups.

In the present invention, the "C ₁ to C ₆ alkoxy group" is an (C ₁ to C ₆ alkyl)-O- group in the above sense unless otherwise specified. Examples include: methoxy, ethyl Oxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, second butoxy, third butoxy, n-pentoxy, 1-methylbutoxy, 2- Groups such as methylbutoxy, 3-methylbutoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy or n-hexyloxy.

In the present invention, "C ₁ to C ₆ haloalkoxy" is a (C ₁ to C ₆ haloalkyl)-O- group with the above meaning unless otherwise specified. The haloalkyl moiety is, for example, difluoro Methoxy, dichloromethoxy, trifluoromethoxy, trichloromethoxy, tribromomethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 1 -Chloroethoxy, 2-chloroethoxy, 1-bromoethoxy, 2-bromoethoxy, 2,2-difluoroethoxy, 1,2-dichloroethoxy, 2,2 -Dichloroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 1,1,2,2-tetrafluoroethoxy, pentafluoroethoxy , 2-bromo-2-chloroethoxy, 2-chloro-1,1,2,2-tetrafluoroethoxy, 1-chloro-1,2,2,2-tetrafluoroethoxy, 1- Chloropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2-bromo-1-methylethoxy, 3-iodopropoxy Group, 2,3-dichloropropoxy, 2,3-dibromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trifluoro-2-propoxy, 3 ,3,3-trichloropropoxy, 3-bromo-3,3-difluoropropoxy, 2,2-difluoropropoxy, 3,3-dichloro-3-fluoropropoxy, 2 ,2,3,3-tetrafluoropropoxy, 1-bromo-3,3,3-trifluoropropoxy, 2,2,3,3,3-pentafluoropropoxy, 2,2,2 -Trifluoro-1-trifluoromethylethoxy, heptafluoropropoxy, heptafluoro-2-propoxy, 1,2,2,2-tetrafluoro-1-trifluoromethylethoxy, 1,1,2,3,3,3-hexafluoropropoxy, 2-chlorobutoxy, 3-chlorobutoxy, 4-chlorobutoxy, 2-chloro-1,1-dimethyl Ethoxy, 4-bromobutoxy, 3-bromo-2-methylpropoxy, 2-bromo-1,1-dimethylethoxy, 2,2-dichloro-1,1-di Methylethoxy, 2-chloro-1-chloromethyl-2-methylethoxy, 4,4,4-trifluorobutoxy, 3,3,3-trifluoro-1-methylpropane Oxygen, 3,3,3-trifluoro-2-methylpropoxy, 2,3,4-trichlorobutoxy, 2,2,2-trichloro-1,1-dimethylethoxy Group, 4-chloro-4,4-difluorobutoxy, 4,4-dichloro-4-fluorobutoxy, 4-bromo-4,4-difluorobutoxy, 2,4-dibromo -4,4-difluorobutoxy, 3,4-dichloro-3,4,4-trifluorobutoxy, 3,3-dichloro-4,4,4-trifluorobutoxy, 4 -Bromo-3,3,4,4-tetrafluorobutoxy, 4-bromo-3-chloro-3,4,4-trifluorobutoxy, 2,2,3,3,4,4-hexa Fluorobutoxy, 2,2,3,4,4,4-hexafluorobutoxy, 2,2,2-trifluoro-1-methyl-1-trifluoromethylethoxy, 3,3 ,3-trifluoro-2-trifluoromethylpropoxy, 2,2,3,3,4,4,4-heptafluorobutoxy, 3,3,4,4,4-pentafluoro-2 -Butoxy, 2,3,3,3-tetrafluoro-2-trifluoromethylpropoxy, 1,1,2,2,3,3, 4,4-octafluorobutoxy, nonafluorobutoxy, perfluoro-third butoxy, 4-chloro-1,1,2,2,3,3,4,4-octafluorobutoxy , 5,5,5-trifluoropentyloxy, 4,4,5,5,5-pentafluoropentyloxy, 3,3,4,4,5,5,5-heptafluoropentyloxy, 3 ,3,4,4,5,5,5-heptafluoro-2-pentyloxy, 2,2,3,3,4,4,5,5,5-nonafluoropentyloxy, 2,2, 3,3,4,4,5,5-octafluoropentyloxy, perfluoropentyloxy, 4,4,5,5,5-pentafluoro-2-butoxy, 2,2-bis(three (Fluoromethyl) propoxy, 2,2,3,3,4,4,5,5,6,6,6-undecylfluorohexyloxy, 3,3,4,4,5,5,6 ,6,6-nonafluorohexyloxy, 4,4,5,5,6,6,6-heptafluorohexyloxy, 2,2,3,3,4,4,5,5,6,6 -Groups such as decafluorohexyloxy, 4,4,4-trifluoro-3,3-bis(trifluoromethyl)butoxy or perfluorohexyloxy.

In the present invention, "C ₃ to C ₆ halocycloalkyl" is a cycloalkyl group having 3 to 6 carbon atoms substituted with the same or different 1 to 11 halogen atoms without particular limitation, for example: 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 1-chlorocyclopropyl, 2-chlorocyclopropyl Group, 2,2-dichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-diiodocyclopropyl, 1-fluorocyclo Butyl, 2-fluorocyclobutyl, 3-fluorocyclobutyl, 3,3-difluorocyclobutyl, heptafluorocyclobutyl, 2-chlorocyclobutyl, 3-chlorocyclobutyl, 3,3 -Dichlorocyclobutyl, 3,3-dibromocyclobutyl, 3,3-diiodocyclobutyl, 1-fluorocyclopentyl, 2-fluorocyclopentyl, 3-fluorocyclopentyl, 2, 2-difluorocyclopentyl, 3,3-difluorocyclopentyl, nonafluorocyclopentyl, 2,2-dichlorocyclopentyl, 3,3-dichlorocyclopentyl, 2,2-dibromo Cyclopentyl, 3,3-dibromocyclopentyl, 2,2-diiodocyclopentyl, 3,3-diiodocyclopentyl, 1-fluorocyclohexyl, 2-fluorocyclohexyl, 3-fluorocyclo Hexyl, 4-fluorocyclohexyl, 2,2-difluorocyclohexyl, 3,3-difluorocyclohexyl, 4,4-difluorocyclohexyl, 1-chlorocyclohexyl, 2-chlorocyclohexyl, 3-chloro Cyclohexyl, 4-chlorocyclohexyl, 2,2-dichlorocyclohexyl, 3,3-dichlorocyclohexyl, 4,4-dichlorocyclohexyl, 3,3-dibromocyclohexyl, 4,4-di Groups such as bromocyclohexyl, 3,3-diiodocyclohexyl or 4,4-diiodocyclohexyl.

In the present invention, "C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkyl" means a halocycloalkyl moiety and the alkyl group has the above meaning (C ₃ to C ₆ halocycloalkane) Group)-(C ₁ to C ₆ alkyl)- group, for example, 2,2-difluorocyclopropylmethyl, 2,2-dichlorocyclopropylmethyl, 1-(2,2- Difluorocyclopropyl)ethyl, 2-(2,2-difluorocyclopropyl)ethyl, 1-(2,2-dichlorocyclopropyl)ethyl, 2-(2,2-dichloro Cyclopropyl)ethyl, 2-(2,2-difluorocyclopropyl)propyl, 3,3-difluorocyclobutylmethyl, 2,2,3,3-tetrafluorocyclobutylmethyl, 2-( 2,2,3,3-tetrafluorocyclobutyl)ethyl, 2-(3,3-difluorocyclobutyl)ethyl, 2-(3,3-difluorocyclobutyl)propyl, 3 , 3-difluorocyclopentylmethyl or 2-(3,3-difluorocyclopentyl)propyl and other groups.

In the present invention, "phenyl C ₁ to C ₃ alkyl" means (phenyl)-(C ₁ to C ₃ alkyl) without limitation, for example, benzyl, 1-phenylethyl , 2-phenylethyl or 2-phenylpropyl and other groups.

In the present invention, "phenyl C ₁ to C ₃ haloalkyl" means (phenyl)-(C ₁ to C ₃ haloalkyl) without particular limitation, for example, 2-phenyl-2, 2-Difluoroethyl and other groups.

唑-2-基、

唑-4-基、

唑-5-基、異

唑-3-基、異

唑-4-基、異

唑-5-基、噻唑-2-基、噻唑-4-基、噻唑-5-基、異噻唑-3-基、異噻唑-4-基、異噻唑-5-基、咪唑-1-基、咪唑-2-基、咪唑-4-基、吡唑-1-基、吡唑-3-基、吡唑-4-基、吡唑-5-基、1,3,4-

二唑-2-基、1,2,3-

二唑-4-基、1,2,3-

二唑-5-基、1,2,4-

二唑-3-基、1,2,4-

二唑-5-基、1,2,5-

二唑-3-基、1,3,4-噻二唑-2-基、1,2,3-噻二唑-4-基、1,2,3-噻二唑-5-基、1,2,4-噻二唑-3-基、1,2,4-噻二唑-5-基、1,2,5-噻二唑-3-基、1,2,4-三唑-3-基、1,2,4-三唑-1-基、1,2,3-三唑-1-基、1,2,3-三唑-2-基、1,3,4-三唑-1-基、四唑-1-基、四唑-2-基、四唑-5-基、吡啶-2-基、吡啶-3-基、吡啶-4-基、嘧啶-2-基、嘧啶-4-基、嘧啶-5-基、嗒

-3-基、嗒

-4-基、吡

-2-基、1,3,5-三

-2-基等基。 In the present invention, "heteroaryl" refers to a 5-membered or 6-membered monocyclic ring having 1 to 6 heteroatoms selected from a nitrogen atom, an oxygen atom, and a sulfur atom, except for carbon atoms. Heterocycles include, 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, iso

Oxazol-3-yl, iso

Oxazol-4-yl, iso

Azole-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-1-yl , Imidazol-2-yl, imidazol-4-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, 1,3,4-

Diazol-2-yl, 1,2,3-

Diazol-4-yl, 1,2,3-

Diazol-5-yl, 1,2,4-

Diazol-3-yl, 1,2,4-

Diazol-5-yl, 1,2,5-

Diazol-3-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1 ,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,5-thiadiazol-3-yl, 1,2,4-triazole- 3-yl, 1,2,4-triazol-1-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,3,4-tri Azole-1-yl, tetrazole-1-yl, tetrazole-2-yl, tetrazole-5-yl, pyrid-2-yl, pyrid-3-yl, pyrid-4-yl, pyrimidin-2-yl , Pyrimidine-4-yl, pyrimidine-5-yl, ta

-3-base, click

-4-yl, pyridine

-2-yl, 1,3,5-tri

-2-yl and other groups.

In the present invention, "heteroaryl C ₁ to C ₃ alkyl" means that the heteroaryl moiety is the same as the above-mentioned (heteroaryl)-(C ₁ to C ₃ alkyl), unless otherwise specified. For example, (pyridin-2-yl)methyl, (pyridin-3-yl)methyl, (pyridin-4-yl)methyl, (thiazol-2-yl)methyl, (thiazol-4-yl )Methyl, (thiazol-5-yl)methyl, (pyrazol-1-yl)methyl, (pyrazol-3-yl)methyl, (pyrazol-4-yl)methyl or (pyrazole -5-yl)methyl and other groups.

In the present invention, the "heteroaryl C ₁ to C ₃ haloalkyl group" is a heteroaryl moiety which is (heteroaryl)-(C ₁ to C ₃ haloalkyl) of the above meaning without particular limitation, for example, Examples include groups such as 2-(pyridin-2-yl)-2,2-difluoroethyl and 2-(pyridin-3-yl)-2,2-difluoroethyl.

In the present invention, “cyano C ₁ to C ₆ alkyl” means (cyano)-(C ₁ to C ₆ alkyl) of the above-mentioned meaning of the alkyl portion without particular limitation, for example, cyano Methyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 3-cyanopropyl, 2-cyanopropan-2-yl, 1-cyanobutyl, 4- Groups such as cyanobutyl, 5-cyanopentyl or 6-cyanohexyl.

In the present invention, the "cyano C ₃ to C ₆ cycloalkyl group", unless otherwise specified, is a cycloalkyl moiety which is (cyano)-(C ₃ to C ₆ cycloalkyl) of the above meaning, for example: Groups such as 1-cyanocyclopropyl, 2-cyanocyclopropyl, 1-cyanocyclobutyl, 3-cyanocyclobutyl, 1-cyanocyclopentyl and the like.

In the present invention, "C ₁ to C ₆ alkoxycarbonyl C ₃ to C ₆ cycloalkyl" means that the alkoxycarbonyl moiety and the cycloalkyl moiety have the above meanings without limitation (C ₁ to C ₆ Alkoxy)-C(=O)-(C ₃ to C ₆ cycloalkyl), for example: 1-methoxycarbonylcyclopropyl, 1-ethoxycarbonylcyclopropyl, 1-n-propyl Groups such as oxycarbonylcyclopropyl, 2-methoxycarbonylcyclopropyl and the like.

In the present invention, "hydroxy C ₁ to C ₆ alkyl" means that the alkyl portion is (hydroxy)-(C ₁ to C ₆ alkyl) in the above meaning without particular limitation, for example, hydroxymethyl, Groups such as 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxybutyl or 4-hydroxybutyl.

In the present invention, "C ₁ to C ₆ alkoxy C ₁ to C ₆ alkyl" is an alkoxy moiety and an alkyl moiety having the above meaning (C ₁ to C ₆ alkoxy)- (C ₁ to C ₆ alkyl)-yl, for example, methoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-methoxy Propyl, 3-methoxypropyl, 2-ethoxypropyl, 3-ethoxypropyl, 1-methyl-3-methoxybutyl or 3-butoxybutyl .

In the present invention, the "mono(C ₁ to C ₆ alkyl)amino group" is an (C ₁ to C ₆ alkyl)-NH- group having the above meaning unless otherwise specified. For example, a: Groups such as amino amine, ethyl amine, n-propyl amine or isopropyl amine.

In the present invention, "di(C ₁ to C ₆ alkyl)amino group" means (C ₁ to C ₆ alkyl) ₂ -N- group, two alkyl The groups may be different from each other, and examples include groups such as a dimethylamino group, a diethylamino group, and N-ethyl-N-methylamino group.

In the present invention, "C ₁ to C ₆ alkylcarbonyl" means (C ₁ to C ₆ alkyl)-C(=O)- group in which the alkyl part has the above meaning unless otherwise specified, for example: Ethyl, propyl, 2-methyl propyl, 2,2-dimethyl propyl, butyl acetyl, 2-methyl butyl acetyl, 3-methyl butyl acetyl, 2-ethyl butyl acetyl, 2,2 -Dimethylbutylamide, 2,3-dimethylbutylamide, 3,3-dimethylbutylamide, pentylamide, 2-methylpentylamide, 3-methylpentylamide, 4-methylpentylamide Radicals or acetylene radicals.

In the present invention, "C ₁ to C ₆ alkoxy C ₁ to C ₆ alkylcarbonyl" is an alkyl portion of the above meaning (C ₁ to C ₆ alkyl)-O-(C ₁ without limitation) To C ₆ alkyl)-C(=O)- group, for example: methoxyethoxyacetyl, ethoxyethoxy, propoxyethoxy, isopropoxyethoxy, butoxy Ethyl acetyl group, 2-methoxy propyl group, 3-methoxy propyl group, 2-ethoxy propyl group, 3-ethoxy propyl group, 2-methoxy butyl group, 4- Groups such as methoxybutyralyl, 2-methoxypentyl, or 5-methoxypentyl.

In the present invention, the "C ₃ to C ₆ cycloalkylcarbonyl group" is a (C ₃ to C ₆ cycloalkyl)-C(=O)- group in the above meaning unless otherwise specified. Examples include groups such as cyclopropanylcarbonyl, cyclobutanylcarbonyl, cyclopentylcarbonyl or cyclohexanecarbonyl.

In the present invention, "C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkylcarbonyl" is a cycloalkyl moiety of the above meaning without particular limitation (C ₃ to C ₆ cycloalkyl C ₁ to C ₆ Alkyl)-C(=O)-yl, for example: 2-cyclopropylacetyl, 2-cyclobutylacetyl, 2-cyclopentylethyl, 2-cyclohexylacetyl , 2-cyclopropylpropionyl or 2-cyclopropylbutyryl and other groups.

In the present invention, the "C ₁ to C ₆ alkoxycarbonyl group" is an alkoxy moiety which is (C ₁ to C ₆ alkoxy)-C(=O)- group in the above meaning without particular limitation, for example, Examples: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, second butoxycarbonyl, third butoxycarbonyl, N-pentyloxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 1-ethylpropoxycarbonyl, 1,1-dimethylpropane Groups such as oxycarbonyl, 1,2-dimethylpropoxycarbonyl or 2,2-dimethylpropoxycarbonyl.

In the present invention, "mono(C ₁ to C ₆ alkyl)aminocarbonyl" is an alkyl moiety of the above meaning (C ₁ to C ₆ alkyl)-NH-C(=O)- Examples include methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, n-butylaminocarbonyl, isobutylaminocarbonyl, and second butyl Aminocarbonyl, third butylaminocarbonyl, n-pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 1 -Ethylpropylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl or n-hexyl Aminocarbonyl and other groups.

In the present invention, the "di(C ₁ to C ₆ alkyl)aminocarbonyl group" is an (C ₁ to C ₆ alkyl) ₂ NC(=O)- group in the above sense, unless otherwise specified. Two alkyl groups may also be different from each other, for example: dimethylaminocarbonyl, diethylaminocarbonyl, di(n-propyl)aminocarbonyl, diisopropylaminocarbonyl, dibutylamine Carbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-isopropyl-N-methylaminocarbonyl, N-butyl-N- Methylaminocarbonyl, N-(second butyl)-N-methylaminocarbonyl, N-isobutyl-N-methylaminocarbonyl, N-pentyl-N-methylaminocarbonyl, Groups such as N-ethyl-N-propylaminocarbonyl, N-ethyl-N-isopropylaminocarbonyl, or N-ethyl-N-butylaminocarbonyl.

In the present invention, "C ₁ to C ₆ alkoxycarbonyl C ₁ to C ₆ alkylamine" is not particularly limited, and examples thereof include: methoxycarbonylmethylamine, ethoxycarbonylmethylamine Group, third butoxycarbonylmethylamine group or 1-[1-(third butoxycarbonyl)ethyl]amine group and other groups.

In the present invention, the "mono(C ₁ to C ₆ alkoxycarbonyl) amine group" is not particularly limited, and examples thereof include: methoxycarbonylamino group, ethoxycarbonylamino group, isopropoxycarbonylamine Group, a third butoxycarbonylamino group or an isobutoxycarbonylamino group.

In the present invention, "(C ₁ to C ₆ alkylthio)carbonyl" means (C ₁ to C ₆ alkylthio)-C(=O )- group, for example, a group such as methylthiocarbonyl, ethylthiocarbonyl, or isopropylthiocarbonyl.

In the present invention, "(C ₁ to C ₆ alkyl)thiocarbonyl" means that the alkyl portion is a (C ₁ to C ₆ alkyl)-C(=S)- group in the above meaning, without particular limitation, Examples include methylthiocarbonyl, ethylthiocarbonyl, n-propylthiocarbonyl, isopropylthiocarbonyl, n-butylthiocarbonyl, isobutylthiocarbonyl, and second butylthio Groups such as carbonyl, tert-butylthiocarbonyl or n-pentylthiocarbonyl.

In the present invention, "(C ₁ to C ₆ alkoxy)thiocarbonyl" refers to (C ₁ to C ₆ alkyl)-OC(=S)- group in which the alkyl portion has the above meaning unless otherwise specified. , For example: methoxythiocarbonyl, ethoxythiocarbonyl, n-propoxythiocarbonyl, isopropoxythiocarbonyl, n-butoxythiocarbonyl, isobutoxythiocarbonyl , Second butoxythiocarbonyl, third butoxythiocarbonyl, n-pentyloxythiocarbonyl, 1-methylbutoxythiocarbonyl, 2-methylbutoxythiocarbonyl, 3 -Methylbutoxythiocarbonyl, 1-ethylpropoxythiocarbonyl, 1,1-dimethylpropoxythiocarbonyl, 1,2-dimethylpropoxythiocarbonyl or 2 , 2-dimethylpropoxythiocarbonyl and other groups.

In the present invention, "mono(C ₁ to C ₆ alkyl)aminothiocarbonyl" means (C ₁ to C ₆ alkyl)-NH-C(= S)- group, for example, methylaminothiocarbonyl, ethylaminothiocarbonyl, n-propylaminothiocarbonyl, isopropylaminothiocarbonyl, n-butylaminothio Carbonyl, isobutylaminothiocarbonyl, second butylaminothiocarbonyl, third butylaminothiocarbonyl, n-pentylaminothiocarbonyl, 1-methylbutylaminothio Carbonyl, 2-methylbutylaminothiocarbonyl, 3-methylbutylaminothiocarbonyl, 1-ethylpropylaminothiocarbonyl, 1,1-dimethylpropylaminothio Groups such as carbonylcarbonyl, 1,2-dimethylpropylaminothiocarbonyl, 2,2-dimethylpropylaminothiocarbonyl or n-hexylaminothiocarbonyl.

In the present invention, “di(C ₁ to C ₆ alkyl)aminothiocarbonyl” means (C ₁ to C ₆ alkyl) ₂ -NC(=S )- group, two alkyl groups may also be different from each other, for example: dimethylaminothiocarbonyl, diethylaminothiocarbonyl, di(n-propyl)aminothiocarbonyl, diisopropylamine Thiocarbonyl, dibutylaminothiocarbonyl, N-ethyl-N-methylaminothiocarbonyl, N-methyl-N-propylaminothiocarbonyl, N-isopropyl- N-methylaminothiocarbonyl, N-butyl-N-methylaminothiocarbonyl, N-(second butyl)-N-methylaminothiocarbonyl, N-isobutyl- N-methylaminothiocarbonyl, N-pentyl-N-methylaminothiocarbonyl, N-ethyl-N-propylaminothiocarbonyl, N-ethyl-N-isopropyl Groups such as aminothiocarbonyl or N-ethyl-N-butylaminothiocarbonyl.

In the present invention, "C ₁ to C ₆ alkylsulfonyl" means that the alkyl portion is a (C ₁ to C ₆ alkyl)-S(=O) ₂ -group having the above meaning without limitation, for example Mentioned: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, second butylsulfonyl Or tertiary butylsulfonyl and other groups.

In the present invention, "C ₁ to C ₆ haloalkylsulfonyl" means (C ₁ to C ₆ haloalkyl)-S(=O) _2- Examples include difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl Group, 3,3,3-trifluoropropylsulfonyl, heptafluoropropylsulfonyl, or heptafluoro-2-propylsulfonyl and other groups.

In the present invention, "mono(C ₁ to C ₆ alkyl)aminosulfonyl" means (C ₁ to C ₆ alkyl)-NH-S(= O)- group, for example: methylaminosulfonyl, ethylaminosulfonyl, n-propylaminosulfonyl, isopropylaminosulfonyl, n-butylaminosulfonyl Group, isobutylaminosulfonyl, second butylaminosulfonyl, third butylaminosulfonyl, n-pentylaminosulfonyl, 1-methylbutylaminosulfonyl Group, 2-methylbutylaminosulfonamide, 3-methylbutylaminosulfonamide, 1-ethylpropylaminosulfonamide, 1,1-dimethylpropylsulfonamide Acyl, 1,2-dimethylpropylaminosulfonyl, 2,2-dimethylpropylaminosulfonyl, or n-hexylaminosulfonyl and other groups.

In the present invention, "di(C ₁ to C ₆ alkyl)aminosulfonyl" means that (C ₁ to C ₆ alkyl) ₂ -NS(=O ) ₂ -group, two alkyl groups may also be different from each other, for example: dimethylaminosulfonyl, diethylaminosulfonyl, bis (n-propylaminosulfonyl), di Isopropylaminosulfonyl, dibutylaminosulfonyl, N-ethyl-N-methylaminosulfonyl, N-methyl-N-propylaminosulfonyl, N- Isopropyl-N-methylaminosulfonyl, N-butyl-N-methylaminosulfonyl, N-(second butyl)-N-methylaminosulfonyl, N- Isobutyl-N-methylaminosulfonamide, N-pentyl-N-methylaminosulfonamide, N-ethyl-N-propylsulfonamide, N-ethyl-N-iso Groups such as propylsulfamoylcarbonyl or N-ethyl-N-butylaminosulfamoyl.

In the present invention, "C ₁ to C ₆ alkoxycarbonyl C ₁ to C ₆ alkyl" is an alkoxy moiety and an alkyl moiety having the above meaning (C ₁ to C ₆ alkoxy) unless otherwise specified. -C(=O)-(C ₁ to C ₆ alkyl)- group, for example: methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycarbonylmethyl, isopropoxycarbonyl Methyl, third butoxycarbonylmethyl, 1-(methoxycarbonyl)ethyl, 2-(methoxycarbonyl)ethyl, 1-(ethoxycarbonyl)ethyl, 2-(ethoxy Carbonyl)ethyl, 1-(methoxycarbonyl)-1-methylethyl, 1-(ethoxycarbonyl)-1-methylethyl, or 2-(third butoxycarbonyl)ethyl基等基。 Base and other base.

In the present invention, "aminocarbonyl C ₁ to C ₆ alkyl" means an H ₂ NC(=O)-(C ₁ to C ₆ alkyl)- group, the alkyl part of which is the above-mentioned meaning, without particular limitation, For example, groups such as carbamoylmethyl, 1-aminomethylethyl, and 2-aminomethylethyl may be mentioned.

In the present invention, "mono(C ₁ to C ₆ alkyl)aminocarbonyl C ₁ to C ₆ alkyl" means that the alkyl portion has the above meaning (C ₁ to C ₆ alkyl) without limitation. NH-C(=O)-(C ₁ to C ₆ alkyl)- group, for example, N-methylaminomethylamide, N-ethylaminemethylamide or N-(section Tributyl) amine methylmethyl and other groups.

In the present invention, "mono(C ₃ to C ₆ cycloalkyl)aminocarbonyl C ₁ to C ₆ alkyl" is a cycloalkyl moiety and an alkyl moiety having the above meanings (C ₃ to C without limitation) ₆ cycloalkyl)-NH-C(=O)-(C ₁ to C ₆ alkyl)- group, for example: N-cyclopropylamine methylamide, N-cyclobutylamine methylamide Groups such as methyl, N-cyclopentylamine, methylmethyl or N-cyclohexylamine, methylmethyl.

In the present invention, "mono(C ₃ to C ₆ halocycloalkyl)aminocarbonyl C ₁ to C ₆ alkyl" is a halocycloalkyl moiety and an alkyl moiety of the above meaning (C ₃ without limitation) To C ₆ halocycloalkyl)-NH-C(=O)-(C ₁ to C ₆ alkyl)- group, for example: N-(2,2-difluorocyclopropyl)aminecarboxamide Methyl and other groups.

In the present invention, "mono(C ₁ to C ₆ haloalkyl)aminocarbonyl C ₁ to C ₆ alkyl" is a haloalkyl moiety of the above meaning (C ₁ to C ₆ haloalkyl) without particular limitation )-NH-C(=O)-(C ₁ to C ₆ alkyl)-yl, for example: N-(2,2-difluoroethyl)amine methylmethyl, N-(2, 2,2-trifluoroethyl)aminomethanylmethyl, 1-{N-(2,2-difluoroethyl)aminomethanyl}ethyl, 1-{N-(2,2-tri (Fluoroethyl)aminecarboxamide]}ethyl, 1-{N-(2,2-difluoroethyl)aminecarboxamide}-1-methylethyl or 1-{N-(2,2 -Trifluoroethyl) amine formyl}-1-methylethyl and other groups.

In the present invention, "di(C ₁ to C ₆ alkyl)aminocarbonyl C ₁ to C ₆ alkyl" means that the alkyl portion has the above meaning (C ₁ to C ₆ alkyl) ₂ without particular limitation. -NC(=O)-(C ₁ to C ₆ alkyl)- group, the two alkyl groups may also be different from each other, for example: N,N-dimethylamine, methyl amide, N,N -Diethylamine methylamide, N,N-dipropylamine methylmethyl, N-ethyl-N-methylamine methylmethyl, N-methyl-N-propyl Aminomethyl and other groups.

In the present invention, "C ₁ to C ₆ alkylcarbonyl C ₁ to C ₆ alkyl" means that the alkyl portion has the above meaning (C ₁ to C ₆ alkyl)-C(=O), without particular limitation -(C ₁ to C ₆ alkyl), for example, acetone, propionylmethyl, 2-methylpropionylmethyl, trimethylpivaloylmethyl, 2-acetoyl Ethyl, 2-propionylethyl, 2(2-methylpropanyl)ethyl, 2-trimethylethenylethyl, 3-ethenylpropyl, 3-propenylpropyl Radicals, 3(2-methylpropionyl)propyl or 3-trimethylacetopropyl and other groups.

In the present invention, "C ₁ to C ₆ haloalkylcarbonyl C ₁ to C ₆ alkyl" is a haloalkyl moiety and an alkyl moiety having the above-mentioned meanings (C ₁ to C ₆ haloalkyl) unless otherwise specified. -C(=O)-(C ₁ to C ₆ alkyl), for example: 2-oxo-3,3-difluoropropyl, 3-chloro-2-oxo-3,3- Difluoropropyl, 2-oxo-3,3,3-trifluoropropyl, 3-oxo-4,4-difluorobutyl, 4-chloro-3-oxo-4,4 -Difluorobutyl, 3-oxo-4,4,4-trifluorobutyl, 3-oxo-4,4,5,5,5-pentafluoropentyl, 4-oxo- 5,5,5-trifluoropentyl or 4-oxo-5,5,6,6,6-pentafluorohexyl and other groups.

In the present invention, “hydroxyimino group C ₁ to C ₆ alkyl group” means, without particular limitation, that the alkyl part has the above meaning HO-N=(C ₁ to C ₆ alkyl group), for example: 1 -(Hydroxyimino)ethyl, 2-(hydroxyimino)ethyl, 1-(hydroxyimino)propyl, 2-(hydroxyimino)propyl or 3-(hydroxyimino) ) Propyl and other groups.

In the present invention, "C ₁ to C ₆ alkoxyimino group" means that (C ₁ to C ₆ alkyl)-ON=C- group whose alkyl portion has the above meaning without particular limitation, for example, : Methoxyimino, ethoxyimino or isopropoxyimino and other groups.

In the present invention, "C ₁ to C ₆ alkoxyimino group C ₁ to C ₆ alkyl group" means that the alkyl portion has the above meaning (C ₁ to C ₆ alkyl group) -ON= (C ₁ to C ₆ alkyl), for example: 1-(methoxyimino)ethyl, 2-(methoxyimino)ethyl, 1-(methoxyimino) Propyl, 2-(methoxyimino)propyl, 3-(methoxyimino)propyl, 1-(ethoxyimino)ethyl, 2-(ethoxyimino) Group) ethyl, 1-(ethoxyimino)propyl, 2-(ethoxyimino)propyl, 3-(ethoxyimino)propyl, 1-(isopropoxy Groups such as imino)ethyl or 2-(isopropoxyimino)ethyl.

In the present invention, "C ₁ to C ₆ haloalkoxyimino group C ₁ to C ₆ alkyl group" means, without particular limitation, that the alkyl portion has the above meaning (C ₁ to C ₆ haloalkyl group)- ON=(C ₁ to C ₆ alkyl), for example: 2-(2,2-difluoroethoxyimino)ethyl, 2-(2,2,2-trifluoroethoxyimino Amino)ethyl, 2-(2,2,2-trifluoroethoxyiminoimino)propyl or 3-(2,2,2-trifluoroethoxyiminoimino)propyl and other groups.

In the present invention, "heterocycloalkyl" means a saturated heterocyclic ring having 3 to 6 members including at least one atom selected from an oxygen atom, a nitrogen atom, and a sulfur atom in addition to a carbon atom, for example, Examples: oxetane-2-yl, oxetane-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl Radicals or tetrahydropyran-4-yl and other radicals.

In the present invention, "heterocyclic alkyl C ₁ to C ₆ alkyl" means a heterocyclic alkyl moiety and the alkyl moiety is (C ₃ to C ₆ heterocycloalkyl)-( C ₁ to C ₆ alkyl), for example: (oxetan-3-yl)methyl, (tetrahydrofuran-2-yl)methyl, (tetrahydrofuran-3-yl)methyl, (tetrahydro Groups such as pyran-2-yl)methyl, (tetrahydropyran-3-yl)methyl or (tetrahydropyran-4-yl)methyl.

In the present invention, "C ₁ to C ₆ alkylthio group" means (C ₁ to C ₆ alkyl)-S- group whose alkyl portion has the above-mentioned meaning, without particular limitation, for example, methylsulfide Group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, second butylthio group or third butylthio group.

In the present invention, the "C ₁ to C ₆ alkylsulfinyl" group is an (C ₁ to C ₆ alkyl)-S(=O)- group in the above meaning unless otherwise specified. For example, Examples: methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, second Groups such as butylsulfinyl or tertiary butylsulfinyl.

In the present invention, "C ₁ to C ₆ haloalkoxy C ₁ to C ₆ alkyl" is a haloalkoxy part of the above meaning (C ₁ to C ₆ haloalkoxy)-( C ₁ to C ₆ alkyl)-yl, for example: 2-(difluoromethoxy)ethyl, 2-(trifluoromethoxy)ethyl, 2-(2,2-difluoroethoxy Radicals) ethyl or 2-(2,2,2-trifluoroethoxy)ethyl and other radicals.

In the present invention, "C ₁ to C ₆ haloalkoxy C ₁ to C ₆ haloalkyl" is a haloalkoxy moiety and a haloalkyl moiety in the above sense (C ₁ to C ₆ halo Alkoxy)-(C ₁ to C ₆ haloalkyl)-yl, for example: 1,1,2-trifluoro-2-(trifluoromethoxy)ethyl, 1,1,2-tri Fluoro-2-(pentafluoroethoxy)ethyl or 1,1,2-trifluoro-2-(heptafluoropropoxy)ethyl and other groups.

In the present invention, "C ₃ to C ₆ cycloalkoxy C ₁ to C ₆ alkyl" is a cycloalkoxy moiety and an alkyl moiety in the above meaning (C ₃ to C ₆ cycloalkoxy) Group)-(C ₁ to C ₆ alkyl), for example, cyclopropoxymethyl, 1-(cyclopropoxy)ethyl, 2-(cyclopropoxy)ethyl, 2-(cyclo Propoxy)propyl, 3-(cyclopropoxy)propyl, 1-methyl-3-(cyclopropoxy)butyl or 3-(cyclopropoxy)butyl, cyclobutoxymethyl Radicals, cyclopentoxymethyl, cyclohexyloxymethyl and other radicals.

In the present invention, "C ₃ to C ₆ halocycloalkoxy C ₁ to C ₆ alkyl" is a halocycloalkoxy moiety and an alkyl moiety in the above sense (C ₃ to C ₆ halo Cycloalkoxy)-(C ₁ to C ₆ alkyl), for example: 2,2-difluorocyclopropoxymethyl, 2,2-dichlorocyclopropoxymethyl, 1-(2 ,2-difluorocyclopropoxy)ethyl, 2-(2,2-difluorocyclopropoxy)ethyl, 1-(2,2-dichlorocyclopropoxy)ethyl, 2-( 2,2-dichlorocyclopropoxy)ethyl, 2-(2,2-difluorocyclopropoxy)propyl, 3,3-difluorocyclobutoxymethyl, 3,3-difluoro Groups such as cyclopentyloxymethyl or 2-(3,3-difluorocyclopentyloxy)propyl.

In the present invention, the "mercapto C ₁ to C ₆ alkyl group" is an HS-(C ₁ to C ₆ alkyl)- group with the above meaning unless otherwise specified. Examples include mercaptomethyl, 1 -Groups such as mercaptoethyl or 2-mercaptoethyl.

In the present invention, "C ₁ to C ₆ alkylthio C ₁ to C ₆ alkyl" is an alkyl portion of the above meaning (C ₁ to C ₆ alkyl)-S-(C ₁ without limitation) To C ₆ alkyl)- group, for example, methylthiomethyl, ethylthiomethyl, n-propylthiomethyl, isopropylthiomethyl, 1-(methylthio )Ethyl, 2-(methylthio)ethyl, 2-(ethylthio)ethyl, 1-(n-propylthio)ethyl, 2-(n-propylthio)ethyl, 1-(isopropylthio)ethyl, 2-(isopropylthio)ethyl, 1-(methylthio)propyl, 2-(methylthio)propyl, 3-(methyl Thio)propyl, 1-(ethylthio)propyl, 2-(ethylthio)propyl, 3-(ethylthio)propyl, 1-(n-propylthio)propyl Group, 2-(n-propylthio)propyl, 3-(n-propylthio)propyl, 1-(methylthio)butyl, 2-(methylthio)butyl, 3- (Methylthio)butyl, 4-(methylthio)butyl, 1-(methylthio)pentyl, 2-(methylthio)pentyl, 3-(methylthio) Amyl, 4-(methylthio)pentyl, 5-(methylthio)pentyl, 2-(n-butylthio)ethyl, 2-(isobutylthio)ethyl, Groups such as dibutylthioethyl, 2-(third butylthio)ethyl, pentylthiomethyl or hexylthiomethyl.

In the present invention, the "C ₁ to C ₆ alkylsulfinyl C ₁ to C ₆ alkyl group" is an alkyl moiety of the above meaning (C ₁ to C ₆ alkyl)-S(= O)-(C ₁ to C ₆ alkyl)-group, for example, methylsulfinylmethyl, ethylsulfinylmethyl, n-propylsulfinylmethyl, isopropyl Sulfonylmethyl, 1-(methylsulfinyl)ethyl, 2-(methylsulfinyl)ethyl, 2-(ethylsulfinyl)ethyl, 1-(n Propylsulfinyl)ethyl, 2-(n-propylsulfinyl)ethyl, 1-(isopropylsulfinyl)ethyl, 2-(isopropylsulfinyl)ethyl Group, 1-(methylsulfinyl)propyl, 2-(methylsulfinyl)propyl, 3-(methylsulfinyl)propyl, 1-(ethylsulfinyl) )Propyl, 2-(ethylsulfinyl)propyl, 3-(ethylsulfinyl)propyl, 1-(n-propylsulfinyl)propyl, 2-(n-propyl Sulfenyl)propyl, 3-(n-propylsulfinyl)propyl, 1-(methylsulfinyl)butyl, 2-(methylsulfinyl)butyl, 3- (Methylsulfinyl)butyl, 4-(methylsulfinyl)butyl, 1-(methylsulfinyl)pentyl, 2-(methylsulfinyl)pentyl, 3-(methylsulfinyl)pentyl, 4-(methylsulfinyl)pentyl, 5-(methylsulfinyl)pentyl, 2-(n-butylsulfinyl) Ethyl, 2-(isobutylsulfinylsulfonyl)ethyl, second butylsulfinylethyl, 2-(third butylsulfinyl)ethyl, pentylsulfinylmethyl Group or hexylsulfinylmethyl group.

In the present invention, "C ₁ to C ₆ alkylsulfonyl C ₁ to C ₆ alkyl" is an alkyl portion of the above meaning (C ₁ to C ₆ alkyl)-S(=O ) ₂ -(C ₁ to C ₆ alkyl)-yl, for example: methylsulfonylmethyl, ethylsulfonylmethyl, n-propylsulfonylmethyl, isopropylsulfonyl Methyl, 1-(methylsulfonyl)ethyl, 2-(methylsulfonyl)ethyl, 2-(ethylsulfonyl)ethyl, 1-(n-propylsulfonyl)ethyl Group, 2-(n-propylsulfonyl)ethyl, 1-(isopropylsulfonyl)ethyl, 2-(isopropylsulfonyl)ethyl, 1-(methylsulfonyl) Propyl, 2-(methylsulfonyl)propyl, 3-(methylsulfonyl)propyl, 1-(ethylsulfonyl)propyl, 2-(ethylsulfonyl)propyl , 3-(ethylsulfonyl)propyl, 1-(n-propylsulfonyl)propyl, 2-(n-propylsulfonyl)propyl, 3-(n-propylsulfonyl)propyl Group, 1-(methylsulfonyl)butyl, 2-(methylsulfonyl)butyl, 3-(methylsulfonyl)butyl, 4-(methylsulfonyl)butyl, 1-(methylsulfonyl)pentyl, 2-(methylsulfonyl)pentyl, 3-(methylsulfonyl)pentyl, 4-(methylsulfonyl)pentyl, 5- (Methylsulfonyl)pentyl, 2-(n-butylsulfonyl)ethyl, 2-(isobutylsulfonyl)ethyl, second butylsulfonylethyl, 2-(section Tributylsulfonyl) ethyl, pentylsulfonylmethyl or hexylsulfonylmethyl and other groups.

In the present invention, "C ₁ to C ₆ haloalkylthio C ₁ to C ₆ alkyl" is a haloalkyl moiety and an alkyl moiety having the above meaning (C ₁ to C ₆ haloalkyl) )-S-(C ₁ to C ₆ alkyl)-yl, 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-(3,3-difluoropropylthio)propyl, 3-( Groups such as 3,3,3-trifluoropropylthio)propyl, 4-(trifluoromethylthio)butyl or 5-(trifluoromethylthio)pentyl.

In the present invention, "C ₁ to C ₆ haloalkylsulfinyl C ₁ to C ₆ alkyl" is a haloalkyl portion and an alkyl portion of the above meaning (C ₁ to C ₆ halo Alkyl)-S(=O)-(C ₁ to C ₆ alkyl)-yl, for example: 2-(difluoromethylsulfinyl)ethyl, 2-(trifluoromethylsulfinyl) Acyl)ethyl, 2-(2,2-difluoroethylsulfinyl)ethyl, 2-(2,2,2-trifluoroethylsulfinyl)ethyl, 2-(3 ,3-difluoropropylsulfinyl)ethyl, 2-(3,3,3-trifluoroethylsulfinyl)ethyl, 3-(difluoromethylsulfinyl)propyl , 3-(trifluoromethylsulfinyl)propyl, 3-(2,2-difluoroethylsulfinyl)propyl, 3-(2,2,2-trifluoroethylsulfinyl Acyl)propyl, 3-(3,3-difluoropropylsulfinyl)propyl, 3-(3,3,3-trifluoropropylsulfinyl)propyl, 4-(tri Fluoromethylsulfinyl)butyl or 5-(trifluoromethylsulfinyl)pentyl and other groups.

In the present invention, "C ₁ to C ₆ haloalkylsulfonyl C ₁ to C ₆ alkyl" is a haloalkyl moiety and an alkyl moiety having the above meanings without particular limitation (C ₁ to C ₆ haloalkane Group)-S(=O) ₂ -(C ₁ to 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-di Fluoropropylsulfonyl)ethyl, 2-(3,3,3-trifluoroethylsulfonyl)ethyl, 3-(difluoromethylsulfonyl)propyl, 3-(trifluoromethyl Sulfosulfonyl)propyl, 3-(2,2-difluoroethylsulfonyl)propyl, 3-(2,2,2-trifluoroethylsulfonyl)propyl, 3-(3 ,3-difluoropropylsulfonyl)propyl, 3-(3,3,3-trifluoropropylsulfonyl)propyl, 4-(trifluoromethylsulfonyl)butyl or 5- (Trifluoromethylsulfonyl) pentyl and other groups.

In the present invention, "C ₃ to C ₆ cycloalkylthio C ₁ to C ₆ alkyl" is a cycloalkyl moiety and an alkyl moiety having the above meanings (C ₃ to C ₆ cycloalkyl) )-S-(C ₁ to C ₆ alkyl)-yl, for example, cyclopropylthiomethyl, cyclopentylthiomethyl, 1-(cyclopropylthio)ethyl or 2- (Cyclopropylthio) ethyl and other groups.

In the present invention, the "C ₃ to C ₆ cycloalkylsulfinyl C ₁ to C ₆ alkyl group" is a cycloalkyl moiety and an alkyl moiety in the above sense (C ₃ to C ₆ Alkyl)-S(=O)-(C ₁ to C ₆ alkyl)-, for example, cyclopropylsulfinylmethyl, cyclopentylsulfinylmethyl, 1-(cyclo Groups such as propylsulfinyl)ethyl or 2-(cyclopropylsulfinyl)ethyl.

In the present invention, "C ₃ to C ₆ cycloalkylsulfonyl C ₁ to C ₆ alkyl" is a cycloalkyl moiety and an alkyl moiety having the above meaning (C ₃ to C ₆ cycloalkyl Group)-S(=O) ₂ -(C ₁ to C ₆ alkyl)- group, for example: cyclopropylsulfonylmethyl, cyclopentylsulfonylmethyl, 1-(cyclopropyl Sulfonyl)ethyl or 2-(cyclopropylsulfonyl)ethyl and other groups.

In the present invention, "C ₃ to C ₆ halocycloalkylthio C ₁ to C ₆ alkyl" is a halocycloalkyl moiety and an alkyl moiety of the above meaning (C ₃ to C ₆ halo Cycloalkyl)-S-(C ₁ to C ₆ alkyl)-yl, for example: 2,2-difluorocyclopropylthiomethyl, 1-(2,2-difluorocyclopropylthio Group) ethyl or 2-(2,2-difluorocyclopropylthio)ethyl and other groups.

In the present invention, "C ₃ to C ₆ halocycloalkylsulfinyl C ₁ to C ₆ alkyl" is a halocycloalkyl moiety and an alkyl moiety of the above meaning (C ₃ to C without limitation) _6- halocycloalkyl)-S(=O)-(C ₁ to C ₆ alkyl)-yl, for example: 2,2-difluorocyclopropylsulfinylmethyl, 1-(2, 2-Difluorocyclopropylsulfinyl)ethyl or 2-(2,2-difluorocyclopropylsulfinyl)ethyl and other groups.

In the present invention, "C ₃ to C ₆ halocycloalkylsulfonyl C ₁ to C ₆ alkyl" is a halocycloalkyl moiety and an alkyl moiety of the above meaning (C ₃ to C ₆ without limitation) Halocycloalkyl)-S(=O) ₂ -(C ₁ to C ₆ alkyl)-yl, for example: 2,2-difluorocyclopropylsulfonylmethyl, 1-(2,2 -Difluorocyclopropylsulfonyl)ethyl or 2-(2,2-difluorocyclopropylsulfonyl)ethyl and other groups.

In the present invention, "C ₁ to C ₆ alkylsulfonyloxy C ₁ to C ₆ alkyl" is an alkylsulfonyloxy moiety and an alkyl moiety of the above meaning (C ₁ without limitation) To C ₆ alkyl)-S(=O) ₂ -O-(C ₁ to C ₆ alkyl)- group, for example, a group such as methanesulfonyloxymethyl.

In the present invention, "C ₁ to C ₆ alkylcarbonylthio C ₁ to C ₃ alkyl" is an alkylcarbonyl sulfur moiety and an alkyl moiety having the above meanings (C ₁ to C ₆ alkyl) )-C(=O)-S-(C ₁ to C ₃ alkyl)- group, for example, groups such as methylcarbonylthiomethyl.

In the present invention, the "amino group C ₁ to C ₆ alkyl group" is an H ₂ N-(C ₁ to C ₆ alkyl group)-based alkyl moiety unless otherwise specified, and examples include amine methyl, 1- Aminoethyl, 2-aminoethyl, 1-aminopropyl, 3-aminopropyl, 2-aminopropane-2-yl, 1-aminobutyl, 4-aminobutyl, Groups such as 5-aminopentyl or 6-aminohexyl.

In the present invention, "mono(C ₁ to C ₆ alkylcarbonyl) amine C ₁ to C ₆ alkyl" is an alkyl portion of the above meaning (C ₁ to C ₆ alkyl)-C without any particular limitation (=O)-NH-(C ₁ to C ₆ alkyl)-yl, for example: 2-(ethylaminoamino)ethyl, 2-(propylaminoamino)ethyl, 2-( Isopropylamino) ethyl, 3-(ethylamino)propyl or 3-(ethylamino)butyl and other groups.

In the present invention, "mono(C ₁ to C ₆ haloalkylcarbonyl)amino C ₁ to C ₆ alkyl" means (C _{1 which} means that the haloalkyl portion and the alkyl portion have the above meanings unless otherwise specified) To C ₆ haloalkyl)-C(=O)-NH-(C ₁ to C ₆ alkyl)- group, for example: chloroethylamidomethyl, dichloroethylamidomethyl , Difluoroethylamidomethyl, trifluoroethylamidomethyl, 1-(trifluoroethylamido)ethyl, 2-(trifluoroethylamido)ethyl, 1 -Groups such as (difluoroethylamido)ethyl or 2-(difluoroethylamido)ethyl.

In the present invention, "mono(C ₃ to C ₆ cycloalkylcarbonyl) amine C ₁ to C ₆ alkyl" is a cycloalkyl moiety and an alkyl moiety in the above sense (C ₃ to C without limitation) ₆ cycloalkyl)-C(=O)-NH-(C ₁ to C ₆ alkyl)-yl, for example: 1-(cyclopropionylamino) ethyl, 1-(cyclopentyl) Amino) ethyl, 2-(cyclopropyl amide amino) ethyl or 2-(cyclopentyl amide amino) ethyl and other groups.

In the present invention, "mono(C ₁ to C ₆ alkoxycarbonyl) amine C ₁ to C ₆ alkyl" is an alkoxy moiety and an alkyl moiety in the above sense (C ₁ to C without limitation) ₆ alkoxy)-C(=O)-NH-(C ₁ to C ₆ alkyl)-yl, for example: 2-(methoxycarbonylamino)ethyl, 2-(ethoxycarbonyl Amino) ethyl or 2-(third butylcarbonylamino) ethyl and other groups.

In the present invention, the "mono(C ₁ to C ₆ alkyl)aminocarbonylamino group C ₁ to C ₆ alkyl" is an alkyl moiety of the above meaning (C ₁ to C ₆ alkyl) unless otherwise specified. -NH-C(=O)-NH-(C ₁ to C ₆ alkyl)- group, for example, methylaminocarbonylaminomethyl, ethylaminocarbonylaminomethyl, isopropylaminocarbonyl Aminomethyl or tertiary butylaminocarbonylaminomethyl and other groups.

In the present invention, "di(C ₁ to C ₆ alkyl)aminocarbonylamino C ₁ to C ₆ alkyl" means that the alkyl portion has the above meaning (C ₁ to C ₆ alkyl) without particular limitation. ) ₂ NC(=O)-NH-(C ₁ to C ₆ alkyl)- group, the alkyl groups may also be different from each other, for example: dimethylaminocarbonylaminomethyl, diethylaminocarbonyl Groups such as aminomethyl or N-methyl-N-ethylaminocarbonylaminomethyl.

In the present invention, "mono(C ₁ to C ₆ alkylsulfonyl)amino group C ₁ to C ₆ alkyl group" means that the alkyl portion has the above meaning (C ₁ to C ₆ alkyl group) without particular limitation. )-S(=O) ₂ -NH-(C ₁ to C ₆ alkyl)-yl, for example: 2-(methylsulfonylamino)ethyl, 2-(ethylsulfonylamino) Group) ethyl, 2-(isopropylsulfonylamido)ethyl, 3-(methylsulfonylamido)propyl or 4-(methylsulfonylamido)butyl and other groups.

In the present invention, "mono(C ₁ to C ₆ haloalkylsulfonyl)amino group C ₁ to C ₆ alkyl" means, without particular limitation, that the haloalkyl portion and the alkyl portion have the above meaning (C ₁ to C ₆ haloalkyl)-S(=O) ₂ -NH-(C ₁ to C ₆ alkyl)- group, for example, 2-(difluoromethylsulfonylamino)ethyl, Groups such as 2-(trifluoromethylsulfonylamino)ethyl, 3-(difluoromethylsulfonylamino)propyl, 3-(trifluoromethylsulfonylamino)propyl and the like.

In the present invention, "N-(C ₁ to C ₆ alkylsulfonyl)-N-(C ₁ to C ₆ alkyl)amino C ₁ to C ₆ alkyl" means the above without limitation. The two hydrogen atoms of the amino group of the amino group C ₁ to C ₆ alkyl group are respectively (C ₁ to C ₆ alkyl)-S(=O) ₂ -group and (C ₁ to C ₆ alkyl)- group Examples of substituted groups include (N-methylsulfonyl-N-methyl)aminomethyl, (N-ethylsulfonyl-N-methyl)aminomethyl, (N-methyl Groups such as sulfamoyl-N-ethyl)aminomethyl or (N-ethylsulfonyl-N-methyl)aminoethyl.

In the present invention, "N-(C ₁ to C ₆ haloalkylsulfonyl)-N-(C ₁ to C ₆ alkyl)amino C ₁ to C ₆ alkyl" means the above without particular limitation The two hydrogen atoms of the amine group C ₁ to C ₆ alkyl group are respectively (C ₁ to C ₆ haloalkyl)-S(=O) ₂ -group and (C ₁ to C ₆ alkyl group)- Examples of the group substituted with a group include (N-difluoromethylsulfonyl-N-methyl)aminomethyl, (N-trifluoromethylsulfonyl-N-methyl)aminomethyl , (N-nonafluorobutylsulfonyl-N-methyl)aminomethyl, (N-difluoromethylsulfonyl-N-ethyl)aminomethyl, (N-trifluoromethyl Sulfonyl-N-ethyl)aminomethyl or (N-nonafluorobutylsulfonyl-N-ethyl)aminomethyl and other groups.

In the present invention, "phenoxy C ₁ to C ₃ alkyl group" means (phenyl)-O-(C ₁ to C ₃ alkyl)- group without particular limitation, for example, phenoxymethyl Radical, 1-phenoxyethyl or 2-phenoxyethyl.

In the present invention, "heteroaryloxy C ₁ to C ₃ alkyl group" means (heteroaryl)-O-(C ₁ to C ₃ alkyl group) whose heteroaryl part has the above meaning unless otherwise specified. -Group, for example, (pyridin-2-yl)oxymethyl, (pyridin-3-yl)oxymethyl, (pyridin-4-yl)oxymethyl, (thiazol-2-yl) Oxymethyl, (thiazol-4-yl)oxymethyl, (thiazol-5-yl)oxymethyl, (pyrazol-1-yl)oxymethyl, (pyrazol-3-yl) Groups such as oxymethyl, (pyrazol-4-yl)oxymethyl or (pyrazol-5-yl)oxymethyl.

In the present invention, "phenyl C ₁ to C3 alkoxy C ₁ to C3 alkyl" means (phenyl)-(C ₁ to C ₃ alkyl)-O-(C ₁ to C without limitation) Examples of ₃ alkyl)-yl include benzyloxymethyl, 1-benzyloxyethyl or 2-benzyloxyethyl.

In the present invention, "heteroaryl C ₁ to C3 alkoxy C ₁ to C3 alkyl" means (heteroaryl)-(C ₁ to C ₃ Group)-O-(C ₁ to C ₃ alkyl)- group, for example, (pyridin-2-yl)methyloxymethyl, (pyridin-3-yl)methyloxymethyl, ( Pyridin-4-yl)methyloxymethyl, (thiazol-2-yl)methyloxymethyl, (thiazol-4-yl)methyloxymethyl, (thiazol-5-yl)methyl Oxymethyl, (pyrazol-1-yl)methyloxymethyl, (pyrazol-3-yl)methyloxymethyl, (pyrazol-4-yl)methyloxymethyl or (Pyrazol-5-yl) methyloxymethyl and other groups.

In the present invention, "phenylthio C ₁ to C 3 alkyl" means (phenyl)-S-(C ₁ to C ₃ alkyl)-, without particular limitation, for example: phenylthio Groups such as methyl, 1-phenylthioethyl or 2-phenylthioethyl.

In the present invention, "phenylsulfinyl C ₁ to C ₃ alkyl" means (phenyl)-S(=O)-(C ₁ to C ₃ alkyl)-yl without limitation, for example Examples include groups such as phenylsulfinylmethyl, 1-phenylsulfinylethyl, or 2-phenylsulfinylethyl.

In the present invention, "phenylsulfonyl C ₁ to C ₃ alkyl" represents (phenyl)-S(=O) ₂ -(C ₁ to C ₃ alkyl)-yl without limitation, for example Examples include groups such as phenylsulfonylmethyl, 1-phenylsulfonylethyl, or 2-phenylsulfonylethyl.

In the present invention, "heteroarylthio C ₁ to C3 alkyl" means that the heteroaryl moiety is the same as the above (heteroaryl)-S-(C ₁ to C ₃ alkyl) unless otherwise specified. -Group, for example, (pyridin-2-yl)thiomethyl, (pyridin-3-yl)thiomethyl, (pyridin-4-yl)thiomethyl, (thiazol-2-yl) Thiomethyl, (thiazol-4-yl)thiomethyl, (thiazol-5-yl)thiomethyl, (pyrazol-1-yl)thiomethyl, (pyrazol-3-yl) Groups such as thiomethyl, (pyrazol-4-yl)thiomethyl or (pyrazol-5-yl)thiomethyl.

In the present invention, "heteroarylsulfinyl C ₁ to C ₃ alkyl" means that the heteroaryl moiety is the same as the above (heteroaryl)-S(=O)-( C ₁ to C ₃ alkyl)-yl, for example: (pyridin-2-yl)sulfinylmethyl, (pyridin-3-yl)sulfinylmethyl, (pyridin-4-yl) Sulfonylmethyl, (thiazol-2-yl)sulfinylmethyl, (thiazol-4-yl)sulfinylmethyl, (thiazol-5-yl)sulfinylmethyl, ( Pyrazol-1-yl)sulfinylmethyl, (pyrazol-3-yl)sulfinylmethyl, (pyrazol-4-yl)sulfinylmethyl or (pyrazole-5- Group) sulfenylmethyl and other groups.

In the present invention, "heteroarylsulfonyl C ₁ to C ₃ alkyl" means that the heteroaryl moiety is the same as the above (heteroaryl)-S(=O) ₂ -( C ₁ to C ₃ alkyl)-yl, for example: (pyridin-2-yl)sulfonylmethyl, (pyridin-3-yl)sulfonylmethyl, (pyridin-4-yl)sulfonyl Methyl, (thiazol-2-yl)sulfonylmethyl, (thiazol-4-yl)sulfonylmethyl, (thiazol-5-yl)sulfonylmethyl, (pyrazol-1-yl ) Sulfonylmethyl, (pyrazol-3-yl)sulfonylmethyl, (pyrazol-4-yl)sulfonylmethyl or (pyrazol-5-yl)sulfonylmethyl and other groups .

In the present invention, "phenyl C ₁ to C ₃ alkylthio C ₁ to C3 alkyl" means (phenyl)-(C ₁ to C ₃ alkyl)-S-(C ₁ without limitation) Examples of the C ₃ alkyl)-yl group include benzylthiomethyl, 1-benzylthioethyl, or 2-benzylthioethyl.

In the present invention, "phenyl C ₁ to C ₃ alkylsulfinyl C ₁ to C ₃ alkyl" means (phenyl)-(C ₁ to C ₃ alkyl)-S( =O)-(C ₁ to C ₃ alkyl)-yl, for example: benzylsulfinylmethyl, 1-benzylsulfinylethyl or 2-benzylsulfinylethyl Equal base.

In the present invention, "phenyl C ₁ to C ₃ alkylsulfonyl C ₁ to C ₃ alkyl" means (phenyl)-(C ₁ to C ₃ alkyl)-S(= O) ₂ -(C ₁ to C ₃ alkyl)-yl, for example, a group such as benzylsulfonylmethyl, 1-benzylsulfonylethyl, or 2-benzylsulfonylethyl.

In the present invention, "heteroaryl C ₁ to C ₃ alkylthio C ₁ to C3 alkyl" means that the heteroaryl portion is the same as the above (heteroaryl)-(C ₁ To C ₃ alkyl)-S-(C ₁ to C ₃ alkyl)-yl, for example: (pyridin-2-yl)methylthiomethyl, (pyridin-3-yl)methylthio Methyl, (pyridin-4-yl)methylthiomethyl, (thiazol-2-yl)methylthiomethyl, (thiazol-4-yl)methylthiomethyl, (thiazole-5- Yl)methylthiomethyl, (pyrazol-1-yl)methylthiomethyl, (pyrazol-3-yl)methylthiomethyl, (pyrazol-4-yl)methylthio Ylmethyl or (pyrazol-5-yl)methylthiomethyl and other groups.

In the present invention, "heteroaryl C ₁ to C ₃ alkylsulfinyl C ₁ to C ₃ alkyl" means that the heteroaryl moiety is the same as the above (heteroaryl) unless otherwise specified. (C ₁ to C ₃ alkyl)-S(=O)-(C ₁ to C ₃ alkyl)-yl, for example: (pyridin-2-yl)methylsulfinylmethyl, (pyridine -3-yl)methylsulfinylmethyl, (pyridin-4-yl)methylsulfinylmethyl, (thiazol-2-yl)methylsulfinylmethyl, (thiazole-4 -Yl)methylsulfinylmethyl, (thiazol-5-yl)methylsulfinylmethyl, (pyrazol-1-yl)methylsulfinylmethyl, (pyrazole-3 -Yl)methylsulfinylmethyl, (pyrazol-4-yl)methylsulfinylmethyl or (pyrazol-5-yl)methylsulfinylmethyl and other groups.

In the present invention, "heteroaryl C ₁ to C ₃ alkylsulfonyl C ₁ to C ₃ alkyl" means that the heteroaryl moiety is the same as the above (heteroaryl)-( C ₁ to C ₃ alkyl)-S(=O) ₂ -(C ₁ to C ₃ alkyl)-yl, for example: (pyridin-2-yl)methylsulfonylmethyl, (pyridine- 3-yl)methylsulfonylmethyl, (pyridin-4-yl)methylsulfonylmethyl, (thiazol-2-yl)methylsulfonylmethyl, (thiazol-4-yl)methyl Sulfonylmethyl, (thiazol-5-yl)methylsulfonylmethyl, (pyrazol-1-yl)methylsulfonylmethyl, (pyrazol-3-yl)methylsulfonyl Groups such as methylmethyl, (pyrazol-4-yl)methylsulfonylmethyl or (pyrazol-5-yl)methylsulfonylmethyl.

In the present invention, "phenylcarbonyl C ₁ to C ₃ alkyl group" means (phenyl)-C(=O)-(C ₁ to C ₃ alkyl)- group without particular limitation, for example: Phenylcarbonylmethyl, 1-phenylcarbonylethyl, 2-phenylcarbonylethyl, 1-phenylcarbonylpropyl, 3-phenylcarbonylpropyl and other groups.

In the present invention, "heteroarylcarbonyl C ₁ to C ₃ alkyl" means that the heteroaryl moiety is the same as the above (heteroaryl)-C(=O)-(C ₁ to C ₃ alkyl)-yl, for example: (pyridin-2-yl)carbonylmethyl, 1-(pyridin-2-yl)carbonylethyl, 2-(pyridin-2-yl)carbonylethyl, 1 -(Pyridin-2-yl)carbonylpropyl, 3-(pyridin-2-yl)carbonylpropyl and other groups.

In the present invention, the "hydroxycarbonyl C ₁ to C ₆ alkyl group" is an HO-C(=O)-(C ₁ to C ₆ alkyl)- group in the above meaning unless otherwise specified. Examples include groups such as hydroxycarbonylmethyl, hydroxycarbonylethyl, and hydroxycarbonylpropyl.

In the present invention, the "C ₁ to C ₆ haloalkylthio group" is a (C ₁ to C ₆ haloalkyl)-S- group in the above sense unless otherwise specified. The haloalkyl moiety is, for example, fluorine Methylthio, difluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, pentafluoroethylthio, 2,2, 2-trichloroethylthio, 3,3,3-trifluoropropylthio, 1,1,2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1, Groups such as 1,1,3,3,3-hexafluoropropane-2-thio, heptafluoropropane-2-thio or 4,4,4-trifluorobutylthio.

In the present invention, "C ₁ to C ₆ haloalkylsulfinyl" is a (C ₁ to C ₆ haloalkyl)-S(=O)- group in the above meaning unless otherwise specified , For example: difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2 ,2-trichloroethylsulfinyl, pentafluoroethylsulfinyl, 3,3,3-trifluoropropylsulfinyl, heptafluoropropylsulfinyl, or heptafluoro-2- Propylsulfinyl and other groups.

In the present invention, the "mono(C ₁ to C ₆ haloalkyl)aminocarbonyl group" is a haloalkyl moiety which is the same as the above (C ₁ to C ₆ haloalkyl)-NH-C unless otherwise specified. (=O)- group, for example: (2,2-difluoroethyl)aminocarbonyl, (2-chloro-2,2-difluoroethyl)aminocarbonyl, (2,2,2- Groups such as trifluoroethyl)aminocarbonyl, (3,3,3-trifluoropropyl)aminocarbonyl or (2,2-difluoropropyl)aminocarbonyl.

In the present invention, "di(C ₁ to C ₆ haloalkyl)aminocarbonyl" is a haloalkyl moiety which is the same as above (C ₁ to C ₆ haloalkyl) ₂ -NC( =O)- group, two haloalkyl groups can also be different from each other, for example: di(2,2-difluoroethyl)aminocarbonyl, di(2,2,2-trifluoroethyl)amine Carbonyl, N-(2,2-difluoroethyl)-N-(2,2,2-trifluoroethyl)aminocarbonyl, N-(2-chloro-2,2-difluoroethyl) -N-(2,2,2-trifluoroethyl)aminocarbonyl or N-(2,2,2-trifluoroethyl)-N-(2,2,2-trifluoropropyl)amino Carbonyl and other groups.

In the present invention, "(1,3-bi- pendant isoindoline-2-yl)C ₁ to C ₃ alkyl" is an alkyl moiety having the same meaning as described above (1, 3-dioxoisoindoline-2-yl)-(C ₁ to C ₃ alkyl)-yl, for example: (1,3-dioxoisoindolin-2-yl Group) methyl and other groups.

In the present invention, "N-(C ₁ to C ₆ alkylsulfonyl)-N-(C ₁ to C ₆ alkyl)amino group", without particular limitation, the two hydrogen atoms of the amine group respectively pass ( C ₁ to C ₆ alkyl)-S(=O) ₂ -group and a group substituted with (C ₁ to C ₆ alkyl)- group, for example: (N-methylsulfonyl-N-methyl )Amino, (N-ethylsulfonyl-N-methyl)amino, (N-methylsulfonyl-N-ethyl)amino or (N-ethylsulfonyl-N-ethyl) Methyl) amine and other groups.

In the present invention, "N-(C ₁ to C ₆ haloalkylsulfonyl)-N-(C ₁ to C ₆ alkyl)amino group" means, without particular limitation, two hydrogen atoms of the amine group Groups substituted with (C ₁ to C ₆ haloalkyl)-S(=O) ₂ -groups and (C ₁ to C ₆ alkyl)- groups, for example: (N-difluoromethylsulfonyl) -N-methyl)amino, (N-trifluoromethylsulfonyl-N-methyl)amino, (N-nonafluorobutylsulfonyl-N-methyl)amino, (N- Difluoromethylsulfonyl-N-ethyl)amine, (N-trifluoromethylsulfonyl-N-ethyl)amine or (N-nonafluorobutylsulfonyl-N-ethyl ) Amino groups and other groups.

In the present invention, the "mono(C ₁ to C ₆ alkylsulfonyl)amino group" is an alkyl moiety of the above meaning (C ₁ to C ₆ alkyl)-S(=O) ₂ unless otherwise specified. The -NH- group includes, for example, groups such as a methylsulfonylamino group, an ethylsulfonylamino group, or an isopropylsulfonylamino group.

In the present invention, the "mono(C ₁ to C ₆ haloalkylsulfonyl)amino group" is a haloalkyl part of the above meaning (C ₁ to C ₆ haloalkyl)-S(= O) ₂ -NH- group, for example, a group such as difluoromethylsulfonylamino group, trifluoromethylsulfonylamino group, difluoromethylsulfonylamino group or the like.

In the present invention, "C ₁ to C ₆ alkylcarbonyloxy C ₁ to C ₃ alkyl" is an alkyl portion of the above meaning (C ₁ to C ₆ alkyl)-C(=O )-O-(C ₁ to C ₃ alkyl)- group, for example, a group such as methylcarbonyloxymethyl.

In the present invention, "C ₁ to C ₆ haloalkylcarbonyloxy C ₁ to C ₃ alkyl" is an alkyl portion of the above meaning (C ₁ to C ₆ haloalkyl)-C( =O)-O-(C ₁ to C ₃ alkyl)- group, for example, groups such as trifluoromethylcarbonyloxymethyl.

In the present invention, the agriculturally acceptable salt, in the compound of the present invention represented by the general formula [I] or [II], when a hydroxyl group, a carboxyl group, an amine group or the like is present in its structure or a nitrogen atom of a pyridine ring means These salts with metals or organic bases or salts of inorganic acids or organic acids; metals can include alkali metals such as sodium or potassium, or alkaline earth metals such as magnesium or calcium, and organic alkalis can include triethylamine or diisopropyl Basic amines, inorganic acids include phosphoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, boric acid, sulfuric acid, etc. Furthermore, organic acids include formic acid, acetic acid, lactic acid, ascorbic acid, succinic acid, fumaric acid Acid, maleic acid, oxalic acid, citric acid, benzoic acid, salicylic acid, tartaric acid, methanesulfonic acid, 4-toluenesulfonic acid or trifluoromethanesulfonic acid, etc.

Next, the 5-(1,2,4-triazol-5-yl)benzene of the present invention represented by the general formula [I] Representative compounds of the compounds of formamide derivatives are exemplified in Tables 1 to 43, and are included in the 5-(1,2,4-triazol-5-yl) of the present invention represented by the general formula [II] Representative compounds of compounds of benzoic acid derivatives are shown in Table 44 to Table 74, and include compounds of the 5-phenyl-1,2,4-triazole derivative of the present invention represented by the general formula [III] Representative examples of compounds are shown in Table 75 to Table 77. However, the compounds included in the derivatives of the present invention are not limited to these. In addition, the compound numbers in the table are referred to in the subsequent description.

In addition, the 5-(1,2,4-triazol-5-yl)benzamide derivatives and 5-(1,2,4-triazol-5-yl)benzoic acid derivatives contained in the present invention Or 5-phenyl-1,2,4-triazole derivative compounds, depending on the type of substituents, there may be geometric isomers of E-form and Z-form, the present invention includes such The arbitrary ratio contains E-body, Z-body, or a mixture of E-body and Z-body. Furthermore, 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, and the present invention includes all optically active substances. , Racemate or diastereomer.

The following symbols in the tables in this specification are as shown below.

Me: methyl;

Et: ethyl;

Pr: n-propyl;

i-Pr: isopropyl or iso-propyl;

t-Bu: tertiary butyl;

Bu: n-butyl

i-Bu: isobutyl or iso-butyl;

s-Bu: second butyl;

Pen: n-pentyl;

Hex: n-hexyl;

c-Pr: cyclopropyl;

c-Bu: cyclobutyl;

c-Pen: cyclopentyl;

c-Hex: cyclohexyl;

CHF ₂ : difluoromethyl;

CF ₃ : trifluoromethyl;

(4-CF ₃ )Ph: 4-trifluoromethylphenyl;

(2-F-4-CF ₃ )Ph: 2-fluoro-4-trifluoromethylphenyl;

(2,2-F ₂ )c-Pr: 2,2-difluorocyclopropyl;

THF: tetrahydrofuran;

THP: tetrahydropyran;

NPhth: phthalimide

On the other hand, the compound of the present invention represented by the general formula [I], [II] or [III] can be produced according to the production method shown below, but it is not limited to these methods. In addition, hereinafter, for example, "a compound represented by the general formula [I]", "a compound represented by the formula [I]", and "compound [I]" all have the same meaning.

<Manufacturing method 1>

Among the compounds of the present invention, the compound represented by the general formula [II-2] can be produced according to the following method, for example.

Trouble typing room to change the "process" in the figure from [0227] to [0440] to "step"

(In the formula, X ¹ represents a halogen atom, R ¹⁰ represents a C ₁ to C ₆ alkyl group, etc., B, R ³ , R ⁴ , R ⁵ , R ⁶ and n represent the same meaning as above)

That is, the compound represented by the general formula [II-2] is a compound represented by the general formula [III-1] that can be obtained in the appropriate solvent (step 1-1) in the presence or absence of an appropriate catalyst After the cyanated compound [III-2], (Step 1-2), the compound represented by the general formula [III-2] is hydrolyzed in an appropriate solvent in the presence of an appropriate acid or base to produce it.

Furthermore, (Step 1-3) In a suitable solvent, the compound represented by the general formula [III-1] is subjected to a carbon monoxide insertion reaction in the presence of a suitable catalyst and a suitable base to obtain the compound of the present invention [ After the compound represented by II-1] (Step 1-4), the compound represented by the general formula [II-1] is hydrolyzed in an appropriate solvent in the presence of an appropriate acid or base to produce the compound [II- 2]. Furthermore, (Step 1-5) In water or a mixed solvent of water and an appropriate solvent, the general formula [III-1] The compound can produce a compound [II-2] by performing a carbon monoxide insertion reaction in the presence of a suitable catalyst and a suitable base.

(Step 1-1)

Examples of the cyanide used in this reaction include sodium cyanide, potassium cyanide, ammonium cyanide, zinc cyanide, copper cyanide, and mixtures thereof. In addition, the amount of cyanide used is usually appropriately selected in the range of 1 to 100 moles relative to 1 mole of compound [III-1], and preferably 1.0 to 5.0 moles.

The catalyst used in this reaction may include tetrakis(triphenylphosphine)palladium, [1,1-bis(diphenylphosphino)ironxin]palladium(II)dichloromethane adduct of dichloride. In addition, the amount of catalyst used is usually appropriately selected in the range of 0.001 to 0.5 moles relative to 1 mole of compound [III-1], and preferably 0.01 to 0.2 moles.

烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯酮、二甲基亞碸、環丁碸(sulfolane)、1,3-二甲基-2-咪唑啉酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；乙腈、丙腈等腈類；乙酸乙酯、乙酸丁酯、丙酸乙酯等酯類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；吡啶、甲基吡啶等吡啶類；水，或此等混合溶劑等。此外，相對於化合物[III-1]1莫耳，溶劑的使用量是0.1至500公升，佳者是0.3至50公升。 Examples of solvents that can be used in this reaction include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane; N,N-dimethylformamide, Non-protons such as N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone Polar polar solvents; alcohols such as methanol, ethanol, 2-propanol; nitriles such as acetonitrile, propionitrile; esters such as ethyl acetate, butyl acetate, ethyl propionate; pentane, hexane, cyclohexane , Aliphatic hydrocarbons such as heptane; pyridines such as pyridine and picoline; water, or mixed solvents such as these. In addition, the amount of the solvent used is 0.1 to 500 liters relative to 1 mole of compound [III-1], preferably 0.3 to 50 liters.

The reaction temperature of this reaction is usually selected from an arbitrary temperature range from -30°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of 0°C to 150°C.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, reaction amount, etc. Different, but usually 10 minutes to 72 hours.

After the reaction is completed, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to separate the compound [III-2]. The isolated compound [III-2] can be purified by using column chromatography, recrystallization, etc. as required.

(Step 1-2)

Examples of acids that can be used in this reaction include inorganic 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 or trifluoromethanesulfonic acid. In addition, the amount of the acid used may be appropriately selected from the range of 1 to the molar amount corresponding to the amount of the solvent relative to 1 mole of the compound [III-2], preferably 1.0 to 100.0 moles.

Examples of the base usable in this 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, and sodium carbonate , Carbonates of alkali metals such as potassium carbonate, and inorganic bases such as alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate. In addition, the amount of the base used may be appropriately selected in the range of 0.1 to 50 moles relative to 1 mole of the compound [III-2], preferably 0.5 to 20.0 moles.

烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；乙腈、丙腈等腈類；丙酮、甲基乙基酮、環己酮等酮類；水或此等混合溶劑等。此外，相對於化合物[III-2]1莫耳，溶劑的使用量是0.1至500公升，佳者是0.3至30公升。 Examples of solvents that can be used in this reaction include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrole Aprotic polar solvents such as ketones, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol; acetonitrile, propionitrile, etc. Nitriles; ketones such as acetone, methyl ethyl ketone, cyclohexanone; water or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 500 liters relative to 1 mole of compound [III-2], preferably 0.3 to 30 liters.

The reaction temperature of this reaction is usually any temperature in the temperature range from -30°C to the reflux temperature of the reaction system, but it is preferably carried out in the range of 0°C to 150°C. good.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, reaction amount, etc., and is usually 10 minutes to 72 hours.

After the reaction is completed, the reaction mixture is poured into water and neutralized, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby isolating the compound [II-2]. The isolated compound [II-2] can be purified by using column chromatography, recrystallization, etc. as required.

(Steps 1-3)

The catalyst system that can be used in this reaction can use a transition metal complex or a combination of a transition metal and a ligand. Examples of the transition metal complex include tetrakis(triphenylphosphine)palladium or dichloro[1,1 '-Bis(diphenylphosphino)ironxin] palladium-dichloromethane adducts, transition metals include: palladium chloride, palladium bromide, palladium acetate, etc., ligands include trimethylphosphine, Triethylphosphine, tributylphosphine, triphenylphosphine, 1,3-bisdimethylphosphinopropane, 1,2-bisdiphenylphosphinoethane, 1,3-bisdiphenylphosphino Propane, etc. In addition, the amount of the catalyst used is 0.001 to 0.1 mol, preferably 0.01 to 0.05 mol, relative to 1 mol of the compound [III-1].

Examples of the base that can be used in this 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; and sodium carbonate , Potassium carbonate and other alkali metal carbonates, sodium bicarbonate, potassium bicarbonate and other alkali metal bicarbonates and other inorganic bases, triethylamine, 4-methylmorpholin, diisopropylethylamine, Organic bases such as 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 4-N,N-dimethylaminopyridine, 2,6-lutidine, etc. In addition, the amount of the base used is 0.1 to 10 moles relative to 1 mole of compound [III-1], preferably 0.1 to 2.0 moles. However, organic bases can also be used as solvents.

烷等醚類；苯、甲苯、二甲苯、氯 苯等芳香族烴類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；乙腈、丙腈等腈類；丙酮、甲基乙基酮、環己酮等酮類；或此等混合溶劑等。此外，相對於化合物[III-1]1莫耳，溶劑的使用量是0.1至500公升，佳者是0.3至30公升。 Examples of solvents that can be used in this reaction include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkanes; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrole Aprotic polar solvents such as ketone, dimethyl sulfoxide, cyproterone, 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol; acetonitrile, propionitrile, etc. Nitriles; ketones such as acetone, methyl ethyl ketone, cyclohexanone; or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 500 liters relative to 1 mole of compound [III-1], preferably 0.3 to 30 liters.

The reaction temperature of this reaction is usually any temperature within a range from -30°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of 0°C to 150°C.

The reaction pressure of this reaction may be any pressure within the range of ordinary atmospheric pressure to 50 atmospheric pressure, and it is preferably carried out in the range of 1 atmospheric pressure to less than 10 atmospheric pressure.

The reaction time of this reaction varies with the reaction temperature, reaction pressure, reaction substrate, reaction amount, etc., and is usually 10 minutes to 72 hours.

After the reaction is completed, the reaction mixture is poured into water and neutralized, and then the precipitated solid is filtered or extracted with an organic solvent and then concentrated to perform operations such as isolation of compound [II-1]. The isolated compound [II-1] can be purified by using column chromatography, recrystallization, etc. as required.

(Steps 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.

After the reaction is completed, the reaction mixture is poured into water and neutralized, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby isolating the compound [II-2]. The isolated compound [II-2] can be purified by using column chromatography, recrystallization, etc. as required.

(Steps 1-5)

The base, solvent, reaction temperature and reaction time that can be used in this reaction are the same as those in steps 1-3 with.

After the reaction is completed, the reaction mixture is poured into water and neutralized, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby isolating the compound [II-2]. The isolated compound [II-2] can be purified by using column chromatography, recrystallization, etc. as required.

<Manufacturing method 2>

Among the compounds of the present invention, the compound represented by the general formula [I-1] can be produced according to the following method, for example.

(In the formula, L ¹ represents a halogen atom, radical OC(=O)OR ¹⁰ , methanesulfonyloxy, trifluoromethanesulfonyloxy, benzenesulfonyloxy or p-toluenesulfonyloxy Group, B, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ¹⁰ and n represent the same meaning as above)

That is, the compound system represented by the general formula [I-1] can (step 2-1) be dissolved in an appropriate In the agent, in the presence or absence of an appropriate catalyst, after compound [II-2] is made into compound [IV] which is an active derivative such as acid halide or mixed acid anhydride, (Step 2-2) It is produced by reacting with compound [V] in the presence of a suitable base in the presence or absence of a suitable base. Furthermore, the compound represented by the general formula [I-1] can also be obtained by (Step 2-3) the compound [II-2] and the compound [V] in the presence of a suitable condensing agent and a suitable base. In the presence, it is produced by reacting in an appropriate solvent.

(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. Reagents converted to other active derivatives can be used: isobutyl chlorocarbonate, mesyl chloride, trifluoromethanesulfonyl chloride, p-toluenesulfonyl chloride, etc. In addition, the amount of the agent converted into the active derivative is appropriately selected in the range of 0.5 to 30 moles relative to 1 mole of the compound [II-2], and preferably 0.5 to 6.0 moles.

Examples of catalysts that can be used in this reaction include N,N-dimethylformamide and the like. In addition, the amount of the catalyst used may be appropriately selected in the range of 0.01 to 1 mole relative to 1 mole of the compound [II-2], and preferably 0.01 to 0.1 mole.

烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；乙腈、丙腈等腈類；乙酸乙酯、乙酸丁酯、丙酸乙酯等酯類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；或此等混合溶劑等。此外，相對於化合物[II-2]1莫耳，溶劑的使用量係使用0.1至100公升，佳者是0.3至10公升。 Examples of solvents that can be used in this reaction include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane; nitriles such as acetonitrile and propionitrile; ethyl acetate , Butyl acetate, ethyl propionate and other esters; pentane, hexane, cyclohexane, heptane and other aliphatic hydrocarbons; or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 100 liters relative to 1 mole of compound [II-2], preferably 0.3 to 10 liters.

The reaction temperature of this reaction is usually any temperature in the temperature range from -30°C to the reflux temperature of the reaction system, but it is preferably carried out in the range of 0°C to 150°C. good.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, reaction amount, etc., and is usually 10 minutes to 24 hours.

After the reaction is completed, concentration and the like are performed, whereby the compound [IV] can be isolated.

(Step 2-2)

The amount of the compound [V] used in the present invention is usually appropriately selected in the range of 1 to 5 moles relative to 1 mole of the compound [IV], preferably 1.0 to 2.5 moles.

Examples of bases that can be used in this reaction include triethylamine, 4-methylmorpholine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, Organic bases such as pyridine, 4-N,N-dimethylaminopyridine, 2,6-lutidine, and alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; calcium hydroxide , Hydroxides of alkaline earth metals such as magnesium hydroxide; carbonates of alkali metals such as sodium carbonate and potassium carbonate; inorganic alkalis such as bicarbonates of alkali metals such as sodium bicarbonate and potassium bicarbonate. In addition, the amount of the base used may be appropriately selected in the range of 1 to 5 mols relative to 1 mol of the compound [IV], preferably 1.0 to 3.5 mols.

烷等醚類等；水，或此等混合溶劑等。此外，相對於化合物[IV]1莫耳，溶劑的使用量是0.1至100公升，佳者是0.3至50公升。 Examples of solvents 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; benzene, Aromatic hydrocarbons such as toluene, xylene and chlorobenzene; esters such as ethyl acetate, butyl acetate and ethyl propionate; nitriles such as acetonitrile and propionitrile; N,N-dimethylformamide, N, Aprotic polar solvents such as N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; Diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkanes; water, or mixed solvents such as these. In addition, the amount of the solvent used is 0.1 to 100 liters relative to 1 mole of compound [IV], preferably 0.3 to 50 liters.

This reaction can be carried out in the presence of a catalyst as required. Butyl ammonium, tetrabutyl ammonium chloride, 15-crown-5, 18-crown-6, etc. In addition, the amount of the catalyst used may be appropriately selected from the range of 0.001 to 1 mole relative to 1 mole of the compound [IV], and preferably 0.01 to 0.1 mole.

The reaction temperature of this reaction may be any temperature in the temperature range from -20°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of 0°C to 80°C.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, reaction amount, etc., and is usually 1 minute to 48 hours.

After the reaction is completed, the reaction mixture is poured into water, and the precipitated solid is filtered or extracted with an organic solvent, followed by concentration, etc., whereby the compound [I-1] can be isolated. The isolated compound [I-1] can be purified by using column chromatography, recrystallization, etc. as required.

(Step 2-3)

The use amount of the compound [V] used in the present invention is appropriately selected in the range of 1 to 3 moles relative to 1 mole of the compound [II-2], and preferably 1.0 to 2.6 moles.

-2-基)-4-甲基嗎啉氯化物、六氟磷酸1H-苯并三唑-1-基氧三(二甲胺基)鏻(phosphonium)、{{[(1-氰基-2-乙氧基-2-側氧基亞乙基)胺基]氧基}-4-嗎啉基亞甲基}二甲基銨六氟磷酸鹽、O-(7-氮雜苯并三唑-1-基)-N,N,N’,N’-四甲基脲鎓(uronium)六氟磷酸鹽、1-羥基苯并三唑或此等混合物等。 Examples of condensing agents that can be used in this reaction include 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-ethyl-3-(3-di Methylaminopropyl) carbodiimide, N,N'-dicyclohexylcarbodiimide, N,N'-diisopropylcarbodiimide, N,N'-carbonyldiimidazole, 4- (4,6-dimethoxy-1,3,5-tri

-2-yl)-4-methylmorpholine chloride, hexafluorophosphate 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium, {{[(1-cyano- 2-ethoxy-2-pentoxyethylene)amino]oxy}-4-morpholinylmethylene}dimethylammonium hexafluorophosphate, O-(7-azabenzotris Azole-1-yl)-N,N,N',N'-tetramethyl uronium hexafluorophosphate, 1-hydroxybenzotriazole, or mixtures of these.

In addition, the amount of the condensing agent used may be appropriately selected in the range of 1 to 3 moles relative to 1 mole of the compound [II-2], preferably 1.0 to 1.2 moles.

When a base is used in this reaction, examples of usable bases include triethylamine, 4-methylmorpholin, diisopropylethylamine, and 1,8-diazabicyclo[5.4.0]-7- Organic bases such as undecene, pyridine, 4-N,N-dimethylaminopyridine, 2,6-lutidine, etc. In addition, the amount of base used may be appropriately selected in the range of 0.1 to 5 moles relative to 1 mole of the compound [II-2], and preferably 0.1 to 3.0 moles.

烷等醚類等；或此等混合溶劑等。此外，相對於化合物[II-2]1莫耳，溶劑的使用量是0.1至100公升，佳者是0.3至80公升。 Examples of solvents 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; and ethyl acetate Esters, butyl acetate, ethyl propionate and other esters; acetonitrile, propionitrile and other nitriles; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2 -Aprotic polar solvents such as pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyl Tetrahydrofuran, 1,4-di

Ethers such as alkanes; or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 100 liters relative to 1 mole of compound [II-2], preferably 0.3 to 80 liters.

This reaction can be carried out in the presence of a catalyst according to the needs. Examples of the catalyst include 4-N,N-dimethylaminopyridine and the like. In addition, the amount of the catalyst used may be appropriately selected in the range of 0.001 to 1 mol relative to 1 mol of the compound [II-2], preferably 0.01 to 0.1 mol.

The reaction temperature of this reaction may be any temperature in the temperature range from -20°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of 0°C to 80°C.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, reaction amount, etc., and is usually 1 minute to 96 hours.

After the reaction is completed, the reaction mixture is poured into water, and the precipitated solid is filtered or extracted with an organic solvent, followed by concentration, etc., whereby the compound [I-1] can be isolated. The isolated compound [I-1] can be purified by using column chromatography, recrystallization, etc. as required.

<Manufacturing method 3>

Among the compounds of the present invention, the compound represented by the general formula [I-3] can be produced according to the following method, for example.

(In the formula, B ¹ represents an oxygen atom or a sulfur atom, L ² represents a halogen atom, methanesulfonyloxy, trifluoromethanesulfonyloxy, nonafluorobutanesulfonyloxy, benzenesulfonyloxy Group, p-toluenesulfonyloxy, methanesulfonyl or ethanesulfonyl, R ^a represents a hydrogen atom, halogen atom, radical C(=O)OR ¹⁰ or radical C(=O)NR ¹ R ² , (R ¹ , R ² , R ³ , R ⁴ , R ⁶ and n represent the same meaning as above)

That is, the compound represented by the general formula [I-3] is a compound represented by the general formula [I-2] and the compound [VI], in the presence or absence of an appropriate base, in the presence of an appropriate radical It is produced by reacting in an appropriate solvent in the presence or absence of the initiator.

The amount of the compound [VI] used in the present invention may be appropriately selected in the range of 1 to 100 moles relative to 1 mole of the compound [I-2], and preferably 1.0 to 3.3 moles.

Examples of the base that can be used in this 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; and sodium carbonate , Alkali carbonates such as potassium carbonate; inorganic alkalis such as alkali metal bicarbonate such as sodium bicarbonate and potassium bicarbonate; metal hydrides such as sodium hydride and potassium hydride; sodium methoxide and ethoxy Metal salts of alcohols such as sodium and potassium tributoxide or triethylamine, N,N-dimethylbenzene Organic bases such as amine, pyridine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, etc. In addition, the amount of the base used may be appropriately selected in the range of 1 to 5 mols relative to 1 mol of the compound [I-2], preferably 1.0 to 2.0 mols.

Examples of the radical initiator that can be used in this reaction include sulfurous acid adducts such as sulfurous acid, sulfite, and Rongalite (trade name, sodium formaldehyde sulfoxylate). In addition, the amount of the radical initiator used is appropriately selected from the range of 0.01 to 5 moles relative to 1 mole of the compound [I-2], and preferably 0.01 to 1.2 moles.

烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；乙腈、丙腈等腈類；乙酸乙酯、乙酸丁酯、丙酸乙酯等酯類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；吡啶、甲基吡啶等吡啶類；水或此等混合溶劑等。此外，相對於化合物[I-2]1莫耳，溶劑的使用量是0.1至100公升，佳者是0.3至10公升。 Examples of solvents that can be used in this reaction include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane; N,N-dimethylformamide, Aprotic polar solvents such as N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone Alcohols; methanol, ethanol, 2-propanol and other alcohols; acetonitrile, propionitrile and other nitriles; ethyl acetate, butyl acetate, ethyl propionate and other esters; pentane, hexane, cyclohexane, heptane Aliphatic hydrocarbons; pyridines such as pyridine and picoline; water or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 100 liters relative to 1 mol of the compound [I-2], preferably 0.3 to 10 liters.

The reaction temperature in this reaction may be any temperature within a range from -30°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of 0°C to 150°C.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, reaction amount, etc., and is usually 10 minutes to 24 hours.

After the reaction is completed, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated, whereby the compound [I-3] can be isolated. The isolated compound [I-3] can be purified by using column chromatography, recrystallization, etc. as required.

<Manufacturing method 4>

Among the compounds of the present invention, the compound represented by the general formula [I-5] can be produced according to the following method, for example.

(In the formula, p represents an integer of 1 or ^{2, R 3, R 4, R} 5, R 6, R a and n have the same meaning as above)

That is, the compound represented by the general formula [I-5] can be produced by oxidizing the compound [I-4] in an appropriate solvent in the presence or absence of an appropriate catalyst.

Examples of oxidizing agents that can be used in this reaction include hydrogen peroxide, m-chloroperoxybenzoic acid, sodium periodate, OXONE (trade name of EI Dupont; potassium peroxysulfate-containing substance), N-chlorosuccinimide Amine, N-bromosuccinimide, tertiary butyl hypochlorite, sodium hypochlorite, etc. In addition, the amount of the oxidizing agent used depends on the oxidation number p of the sulfur atom of the compound represented by the general formula [I-5], but it is appropriate in the range of 0.8 to 10 mol relative to 1 mol of the compound [I-4] The local choice is sufficient. The best is 0.8 to 4.0 moles.

Examples of catalysts that can be used in this reaction include sodium tungstate and the like. In addition, the amount of the catalyst used may be appropriately selected in the range of 0.01 to 1.0 moles relative to 1 mole of the compound [I-4], preferably 0.01 to 0.1 moles.

Examples of solvents that can be used in this reaction include aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; N,N-dimethylformamide, N,N-dimethylacetamide, and N- Methyl-2-pyrrole Aprotic polar solvents such as ketones, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol; dichloromethane, chloroform , 1,2-dichloroethane and other halogenated hydrocarbons; pentane, hexane, cyclohexane, heptane and other aliphatic hydrocarbons; acetic acid, water or these mixed solvents, etc. In addition, the amount of the solvent used is 0.1 to 100 liters relative to 1 mol of the compound [I-4], preferably 0.3 to 15 liters.

The reaction temperature of this reaction is usually any temperature within a range from -30°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of -10°C to 100°C.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, reaction amount, etc., and is usually 10 minutes to 24 hours.

After the reaction is completed, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated, whereby the compound [I-5] can be isolated. The isolated compound [I-5] can be purified by using column chromatography, recrystallization, etc. as required.

<Manufacturing method 5>

Among the compounds of the present invention, the compound represented by the general formula [I-8] can be produced according to the following method, for example.

(Wherein, R ^b represents a C ₁ to C ₆ alkyl or a C ₁ to C ₆ ^{haloalkyl, R 3, R 4, R} 6, R a and n have the same meaning as above)

That is, the compound represented by the general formula [I-8] can be obtained by reacting the compound [I-6] and the compound [VII] in an appropriate solvent in (Step 5-1) to obtain the compound [I-7], (Step 5-2) The compound [I-7] is produced by hydrolysis reaction in an appropriate solvent in the presence or absence of an appropriate base.

(Step 5-1)

Examples of the compound [VII] usable in this reaction include acetic anhydride or trifluoroacetic anhydride. In addition, the amount of the compound [VII] used may be selected from the range of 1 mole to a sufficient amount used as a solvent relative to 1 mole of the compound [I-6], and preferably 1.0 to 5.0 moles.

烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類，甲醇、乙 醇、2-丙醇等醇類；乙腈、丙腈等腈類；乙酸乙酯、乙酸丁酯、丙酸乙酯等酯類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；水或此等混合溶劑等。此外，相對於化合物[I-6]1莫耳溶劑的使用量是，0.1至100公升，佳者是0.3至10公升。 Examples of solvents that can be used in this reaction include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkanes; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; halogenated hydrocarbons such as methylene chloride, chloroform, and 1,2-dichloroethane; and alcohols such as methanol, ethanol, and 2-propanol ; Nitriles such as acetonitrile, propionitrile; esters such as ethyl acetate, butyl acetate, ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane; water or these mixed solvents, etc. . In addition, the amount of 1 mol solvent used relative to compound [I-6] is 0.1 to 100 liters, preferably 0.3 to 10 liters.

The reaction temperature in this reaction may be any temperature within a range of -10°C to the reflux temperature of the reaction system in any reaction, and it is preferably carried out in a temperature range of 0°C to 50°C.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, reaction amount, etc. in any reaction, and is usually 5 minutes to 24 hours.

After the reaction is completed, the reaction mixture is poured into water, etc., extracted with an organic solvent, and concentrated to perform operations such that the compound [I-7] can be isolated. The isolated compound [I-7] can be purified by using column chromatography, recrystallization, etc. as required. In addition, the 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 steps 1-2 of Production Method 1.

After the reaction is completed, the reaction mixture is poured into water and neutralized, and then the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to separate the compound [I-8]. The isolated compound [I-8] can be purified by using column chromatography, recrystallization, etc. as required.

<Manufacturing method 6>

Among the compounds of the present invention, the compound represented by the general formula [I-9] is, for example, a compound represented by the general formula [I-1] and can be produced according to the following method.

(In the formula, B, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and n represent the same meaning as described above). That is, the compound represented by the general formula [I-9] can be produced by reacting the compound [I-1] and an appropriate vulcanizing agent in the presence or absence of an appropriate base.

Examples of vulcanizing agents that can be used in this reaction include phosphorus pentasulfide and Lawesson's Reagent (Lawesson's Reagent: 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphos Thiadiphosphetane-2,4-disulfide) etc. In addition, the amount of the vulcanizing agent used may be appropriately selected in the range of 0.5 to 30 moles relative to 1 mole of the compound [I-1], preferably 0.5 to 5.0 moles.

In this reaction, it is not necessary to add a base. However, when a base is used, the base that can be used is, for example, inorganic bases such as sodium carbonate, potassium carbonate and other alkali metal carbonates or triethylamine, N,N- Organic bases such as dimethylaniline, pyridine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5,4,0]-7-undecene, etc. In addition, the amount of the base used may be appropriately selected in the range of 0.01 to 10 moles relative to 1 mole of compound [I-1], and preferably 0.1 to 2.0 moles.

烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；二甲基亞碸、環丁碸等非質子性極性溶劑類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；水或此等混合溶劑等。此外，相對於化合物[I-1]1莫耳，溶劑的使用量是0.1至300公升，佳者是0.3至50公升。 Examples of solvents that can be used in this reaction include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkanes; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as dimethyl sulfoxide and cyclobutane; dichloromethane, chloroform, 1,2-dichloroethane Halogenated hydrocarbons such as alkanes; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane; water or these mixed solvents; In addition, the amount of the solvent used is 0.1 to 300 liters relative to 1 mol of the compound [I-1], preferably 0.3 to 50 liters.

The reaction temperature of this reaction is usually any temperature within a range from -70°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of 0°C to 150°C.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, reaction amount, etc., and is usually 10 minutes to 24 hours.

After the reaction is completed, the reaction mixture is poured into water, extracted with an organic solvent, and subjected to operations such as concentration, whereby the compound [I-9] can be isolated. Alternatively, the compound [I-9] may be isolated by concentrating the solvent from the reaction mixture. The isolated compound [I-9] can be purified by using column chromatography, recrystallization, etc. as required.

<Manufacturing method 7>

Among the compounds of the present invention, the compound represented by the general formula [I-11] is, for example, a compound represented by the general formula [I-10] and can be produced according to the following method.

(In the formula, B, R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ and X ¹ represent the same meaning as described above)

The cyanide, catalyst, solvent, reaction temperature and reaction time that can be used in this reaction are the same as Step 1-1 of Production Method 1.

After the reaction is completed, the reaction mixture is injected into water and neutralized, and the precipitated solid is filtered or extracted with an organic solvent and then concentrated, thereby isolating the compound [I- 11]. The isolated compound [I-11] can be purified by using column chromatography, recrystallization, etc. as required.

<Manufacturing method 8>

Among the compounds of the present invention, the compound represented by the general formula [I-1] can be produced according to the following method using, for example, a compound represented by the general formula [III-1].

(In the formula, B, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , n, and X ¹ represent the same meaning as described above)

That is, the compound represented by the general formula [I-1] is a compound and the compound [V] represented by the general formula [III-1] can be carried out in a suitable solvent in the presence of a suitable catalyst and a suitable base Manufactured by carbon monoxide insertion reaction.

The amount of the compound [V] used in the present invention is usually appropriately selected in the range of 1 to 5 moles relative to 1 mole of the compound [III-1], preferably 1.0 to 3.0 moles.

For the catalyst that can be used in this reaction, a transition metal complex or a combination of a transition metal and a ligand is used. For example, the transition metal complex may be tetrakis(triphenylphosphine)palladium or dichloro[ 1,1'-bis(diphenylphosphino)ferroxin]palladium-dichloromethane adducts, transition metals can be mentioned: palladium chloride, palladium bromide, palladium acetate, etc., ligands can be mentioned: trimethyl Phosphine, triethylphosphine, tributylphosphine, triphenylphosphine, 1,3-bisdimethylphosphinopropane, 1,2-bisdiphenylphosphinoethane, 1,3-bisdiphenyl Phosphinyl propane and so on. In addition, relative to the compound [III-1] 1 mole, the amount of catalyst used is 0.001 to 0.1 mol, the better is 0.01 to 0.05 mol.

Examples of the base usable in this 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, and sodium carbonate , Potassium carbonate and other alkali metal carbonates, sodium bicarbonate, potassium bicarbonate and other alkali metal bicarbonates and other inorganic bases, triethylamine, 4-methylmorpholin, diisopropylethylamine, Organic bases such as 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 4-N,N-dimethylaminopyridine, 2,6-lutidine, etc. In addition, the amount of the base used is 0.1 to 10 moles relative to 1 mole of compound [III-1], preferably 0.1 to 7.0 moles. However, organic bases can also be used as solvents.

烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇等醇類；乙腈、丙腈等腈類；丙酮、甲基乙基酮、環己酮等酮類；或此等混合溶劑等。此外，相對於化合物[III-1]1莫耳，溶劑的使用量是0.1至500公升，佳者是0.5至30公升。 Examples of solvents that can be used in this reaction include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkanes; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrole Aprotic polar solvents such as ketone, dimethyl sulfoxide, cyproterone, 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol; acetonitrile, propionitrile, etc. Nitriles; ketones such as acetone, methyl ethyl ketone, cyclohexanone; or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 500 liters relative to 1 mole of compound [III-1], preferably 0.5 to 30 liters.

The reaction temperature of this reaction is usually any temperature within a range from -30°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of 0°C to 150°C.

The reaction pressure of this reaction may be any pressure within a range of usually atmospheric pressure to 50 atmospheres, and preferably, it is preferably carried out in a range of 1 atmosphere to less than 10 atmospheres.

The reaction time of this reaction varies with the reaction temperature, reaction pressure, reaction substrate, reaction amount, etc., and is usually 10 minutes to 72 hours.

After the reaction is completed, the reaction mixture is poured into water and after neutralization, it is filtered out The extracted solid may be extracted with an organic solvent and then subjected to operations such as concentration to isolate the compound [I-1]. The isolated compound [I-1] can be purified by using column chromatography, recrystallization, etc. as required.

<Manufacturing method 9>

Among the compounds of the present invention, the compound represented by the general formula [I-12] is, for example, a compound represented by the general formula [XXIII] and a compound represented by [XXIV], and can be produced according to the following method.

(In the formula, R ¹¹ represents a C ₁ to C ₆ alkyl group or a C ₁ to C ₆ haloalkyl group, R ¹² represents a hydrogen atom, a group C(=O)OR ¹⁰ or a group C(=O)NR ¹ R ² , R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ¹⁰ , n, and X ^{1 have the} same meaning as described above. In particular, B in the general formula of the compound represented by [XXIV] represents a boron atom)

That is, the compound represented by the general formula [I-12] can carry out the compound represented by the general formula [XXIII] and the compound [XXIV] in the presence of an appropriate catalyst and an appropriate base in an appropriate solvent. Manufactured by coupling reaction of Miyaura.

The amount of the compound [XXIV] used in the present invention is usually appropriately selected in the range of 1 to 5 moles relative to 1 mole of the compound [XXIII], preferably 1.0 to 1.5 moles.

The catalyst that can be used in this reaction may use a transition metal complex or a combination of a transition metal and a ligand. For example, the transition metal complex may include tetrakis(triphenylphosphine)palladium or dichloro[1 ,1'-bis(diphenylphosphino)ironxin]palladium-dichloromethane adducts, transition metals include: chlorination Palladium, palladium bromide, palladium acetate, etc., ligands include trimethylphosphine, triethylphosphine, tributylphosphine, triphenylphosphine, 1,3-bisdimethylphosphinopropane, 1, 2-bisdiphenylphosphinoethane, 1,3-bisdiphenylphosphinopropane, etc. In addition, the amount of catalyst used is 0.001 to 0.2 moles relative to 1 mole of compound [XXIII], preferably 0.01 to 0.15 moles.

Examples of the base that can be used in this 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; and sodium carbonate , Potassium carbonate and other alkali metal carbonates; sodium bicarbonate, potassium bicarbonate and other alkali metal bicarbonates and other inorganic bases, triethylamine, 4-methylmorpholin, diisopropylethylamine, Organic bases such as 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 4-N,N-dimethylaminopyridine, 2,6-lutidine, etc. In addition, the amount of the base used is 0.1 to 10 moles relative to 1 mole of compound [XXIII], and preferably 0.1 to 4.0 moles.

烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等非質子性極性溶劑類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；甲醇、乙醇、2-丙醇等醇類；乙腈、丙腈等腈類；丙酮、甲基乙基酮、環己酮等酮類；水或此等混合溶劑等。此外，相對於化合物[XXIII]1莫耳，溶劑的使用量是0.1至500公升，佳者是0.3至30公升。 Examples of solvents that can be used in this reaction include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrole Aprotic polar solvents such as ketones, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane Alcohols such as methanol, ethanol and 2-propanol; nitriles such as acetonitrile and propionitrile; ketones such as acetone, methyl ethyl ketone and cyclohexanone; water or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 500 liters relative to 1 mole of compound [XXIII], preferably 0.3 to 30 liters.

The reaction temperature of this reaction is usually any temperature within a range from -30°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of 0°C to 150°C.

The reaction time of this reaction depends on the reaction temperature, reaction pressure, reaction matrix, reaction The amount varies depending on the amount, usually 10 minutes to 72 hours.

After the reaction is completed, the reaction mixture is poured into water, extracted with an organic solvent, and subjected to operations such as concentration, whereby the compound [I-12] can be isolated. Alternatively, the solvent may be concentrated from the reaction mixture to isolate the compound [I-12]. The isolated compound [I-12] can be purified by using column chromatography, recrystallization, etc. as required.

<Manufacturing method 10>

Among the compounds of the present invention, the compound represented by the general formula [I-14] is, for example, a compound represented by the general formula [I-13] and can be produced according to the following method.

(In the formula, R ^e represents a hydrogen atom, a halogen atom or a radical C(=O)NR ¹ R ² , R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ¹⁰ and n represent the same meaning as above)

That is, the compound represented by the general formula [I-14] can be produced by hydrolyzing the compound represented by the general formula [I-13] in the presence of an appropriate acid or base in an appropriate solvent.

The solvents, acids, bases, reaction temperature and reaction time that can be used in this reaction are the same as Steps 1-4 of Production Method 1.

After the reaction is completed, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to separate the compound [I-14]. The isolated compound [I-14] can be purified by using column chromatography, recrystallization, etc. as required.

<Manufacturing method 11>

Among the compounds of the present invention, the compound represented by the general formula [I-17] is, for example, a compound represented by the general formula [I-15] and can be produced according to the following method.

(In the formula, R ¹³ represents a hydrogen atom or a radical C(=O)OR ¹⁰ , R ¹ , R ² , R ³ , R ⁴ , R ⁶ , R ¹⁰ , R ^a and n represent the same meaning as above)

That is, the compound represented by the general formula [I-17] can be used in a suitable solvent in the presence of a suitable base, the compound represented by the general formula [I-15] and diphenyl phosphate azide (DPPA) The isocyanate [I-16] produced by the reaction is produced by adding the compound R ¹⁰ OH as a nucleophile.

The amount of DPPA that can be used in this reaction is appropriately selected in the range of 1 to 5 moles relative to 1 mole of compound [I-15], and preferably 1.0 to 2.5 moles.

The bases that can be used in this reaction include triethylamine, N,N-dimethylaniline, pyridine Organic bases such as pyridine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, lithium hydroxide, sodium hydroxide, potassium hydroxide, etc. Hydroxides of alkali metals, hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide, carbonates of alkali metals such as sodium carbonate and potassium carbonate, and heavy metals such as sodium bicarbonate and potassium bicarbonate Inorganic bases such as carbonates. In addition, the amount of the base used may be appropriately selected in the range of 1 to 5 moles relative to 1 mole of the compound [I-15], preferably 1.0 to 2.5 moles.

烷等醚類等；水，或此等混合溶劑等。此外，相對於化合物[I-15]1莫耳，溶劑的使用量是0.1至300公升，佳者是0.1至100公升。 Examples of solvents 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; benzene, Aromatic hydrocarbons such as toluene, xylene, chlorobenzene; alcohols such as methanol, ethanol, 2-propanol; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl Aprotic polar solvents such as di-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkanes; water, or mixed solvents such as these. In addition, the amount of the solvent used is 0.1 to 300 liters relative to 1 mol of the compound [I-15], preferably 0.1 to 100 liters.

Nucleophilic agents usable in this reaction include, for example, alcohols such as methanol, ethanol, 2-propanol, and tert-butyl alcohol, water, and the like. In addition, the amount of the nucleophilic agent used may be selected from the range of 1 mole to a sufficient amount used as a solvent with respect to 1 mole of the compound [I-15], and preferably 1.0 to 100 moles.

The reaction temperature in this reaction may be any temperature within a range from -20°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of 0°C to 120°C.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, and reaction amount, and is usually 1 minute to 48 hours.

After the reaction is completed, the reaction mixture is poured into water, and the precipitated solid or After the organic solvent is extracted, concentration and other operations are performed, whereby the compound [I-17] can be isolated. The isolated compound [I-17] can be purified by using column chromatography, recrystallization, etc. as required.

<Manufacturing method 12>

Among the compounds of the present invention, the compound represented by the general formula [I-19] is, for example, a compound represented by the general formula [I-18] and can be produced according to the following method.

(Wherein, X ³ represents a hydrogen atom, a halogen atom or a ^{cyano, R 3, R 4, R} 6, R a and n have the same meaning as above)

That is, the compound represented by the general formula [I-19] is a compound represented by the general formula [I-18] in an appropriate solvent, according to Organic Synthesis, Coll. Vol. 3, page 195 (1955) After the method (for example, a method using inorganic acids such as hydrochloric acid, sulfuric acid, hydrobromic acid, and nitrite or alkyl nitrite) becomes a diazonium salt, it may or may not be in the presence of copper halide or copper cyanide In the presence, it is produced by reacting in an appropriate solvent.

Examples of the copper halide that can be used in this reaction include copper (I), copper (I) bromide, copper (I) iodide, copper (II) chloride, and copper (II) bromide. In addition, the use amount of copper halide or copper cyanide is 1 to 5 moles, preferably 1.0 to 2.5 moles relative to 1 mole of compound [I-18].

烷等醚類；苯、甲苯、二甲苯、氯 苯等芳香族烴類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；乙腈、丙腈等腈類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等非質子性極性溶劑類；鹽酸、硫酸等無機酸類；乙酸等羧酸類；水或此等混合溶劑等。此外，相對於化合物[I-18]1莫耳，溶劑的使用量是0.1至100公升，佳者是0.3至10公升。 Examples of solvents that can be used in this reaction include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane; nitriles such as acetonitrile and propionitrile; N, N -Dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazole Aprotic polar solvents such as porphyrin; inorganic acids such as hydrochloric acid and sulfuric acid; carboxylic acids such as acetic acid; water or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 100 liters relative to 1 mol of the compound [I-18], preferably 0.3 to 10 liters.

The reaction temperature in this reaction may be any temperature within a range from -70°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of -20°C to 100°C.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, reaction amount, etc., and is usually 10 minutes to 24 hours.

After the reaction is completed, the reaction mixture is poured into water and neutralized, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated, thereby isolating the compound [I-19]. The isolated compound [I-19] can be purified by using column chromatography, recrystallization, etc. as required.

<Manufacturing method 13>

Among the compounds of the present invention, the compound represented by the general formula [I-20] is, for example, a compound represented by the general formula [I-13] and can be produced according to the following method.

^{(Wherein, R 3, R 4, R} 6, R 10, R e , and n have the same meaning as above)

That is, the compound represented by the general formula [I-20] can be Good), "Reducing General Items" in Volume 26, which is produced by reducing the compound represented by the general formula [I-13].

<Manufacturing method 14>

Among the compounds of the present invention, the compound represented by the general formula [I-22] can be produced according to the following method, for example.

(Wherein, B ² represents an oxygen atom, a sulfur atom, a group ^{-N (-R 7) -, L} 2, R 3, R 4, R 5, R 6, R 7, R e and n are the same as defined above significance)

That is, the compound represented by the general formula [1-22] may (step 14-1) convert the compound [I-20] into the compound [I in an appropriate solvent in the presence or absence of an appropriate base After -21], (Step 14-2) is produced by reacting with compound [XXVII] in an appropriate solvent in the presence or absence of an appropriate base. Furthermore, the compound represented by the general formula [1-22] may also be present in a suitable solvent in the presence of azodicarboxylate diester (azodicarboxylate diester) and triphenylphosphine Next, the compound [I-20] and the compound [XXVII] are reacted to produce.

(Step 14-1)

The compound represented by the general formula [I-21] can be produced by reacting the compound represented by the general formula [I-20] in the presence of a halogenating agent or a halogenating agent and triphenylphosphine in an appropriate solvent.

Examples of the halogenating agent used in this reaction 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, etc. In addition, the amount of the halogenating agent used may be appropriately selected from the range of 0.5 to the molar equivalent of the amount of the solvent relative to 1 mole of the compound [I-20], preferably 1.0 to 100 molar.

The use amount of triphenylphosphine used in this reaction is appropriately selected in the range of 1 to 5 moles relative to 1 mole of compound [I-20], preferably 1.0 to 2.5 moles.

In addition, the compound represented by the general formula [I-21] can be produced by reacting the compound represented by the general formula [I-20] in the presence of a pseudo halogenating agent in an appropriate solvent.

Examples of the pseudohalogenating agent used in this reaction include trifluoromethanesulfonic anhydride, trifluoromethanesulfonyl chloride, and p-toluenesulfonyl chloride. In addition, the amount of the pseudohalogenating agent used may be appropriately selected in the range of 0.5 to 10 moles relative to 1 mole of the compound [I-20], preferably 0.5 to 5.0 moles.

When a base is used in this reaction, the base that can be used includes, for example, 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 Types; alkali carbonates such as sodium carbonate and potassium carbonate; inorganic bases such as alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydrides such as sodium hydride and potassium hydride; sodium methoxide , Sodium ethoxylate, potassium tributoxide and other metal salts of alcohol or triethylamine, 4-methylmorpholin, diisopropylethylamine, 1,8-diazabicyclo[5.4.0 ]-7-undecene, pyridine, 4- Organic bases such as N,N-dimethylaminopyridine and 2,6-lutidine. In addition, the amount of the base used may be appropriately selected in the range of 0.1 to 20 moles relative to 1 mole of the compound [I-20], preferably 0.5 to 6.0 moles.

烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；乙腈、丙腈等腈類；乙酸乙酯、乙酸丁酯、丙酸乙酯等酯類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；或此等混合溶劑等。此外，相對於化合物[I-20]1莫耳，溶劑的使用量是0.1至100公升，佳者是0.3至10公升。 Examples of solvents that can be used in this reaction include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane; nitriles such as acetonitrile and propionitrile; ethyl acetate , Butyl acetate, ethyl propionate and other esters; pentane, hexane, cyclohexane, heptane and other aliphatic hydrocarbons; or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 100 liters relative to 1 mol of the compound [I-20], preferably 0.3 to 10 liters.

The reaction temperature of this reaction is usually any temperature within a range from -30°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of 0°C to 150°C.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, reaction amount, etc., and is usually 10 minutes to 48 hours.

After the reaction is completed, the reaction mixture is poured into water, extracted with an organic solvent, concentrated, etc., whereby the compound [I-21] can be isolated. The isolated compound [I-21] can be purified by using column chromatography, recrystallization, etc. as required.

(Step 14-2)

The amount of the compound [XXVII] that can be used in this reaction is appropriately selected from the range of 1 to 5 moles relative to 1 mole of the compound [I-21], and preferably 1.0 to 2.5 moles.

Examples of the base that can be used in this 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; and sodium carbonate , Potassium carbonate and other alkali metal carbonates; sodium bicarbonate, potassium bicarbonate and other alkali gold Inorganic bases such as bicarbonates; metal hydrides such as sodium hydride and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethoxylate, and potassium tributoxide; or triethylamine, 4-methylmorpholin, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 4-N,N-dimethylaminopyridine, 2 , 6-lutidine and other organic bases. In addition, the amount of the base used may be appropriately selected in the range of 1 to 5 moles relative to 1 mole of the compound [I-21], and preferably 1.0 to 3.0 moles.

烷等醚類等；水，或此等混合溶劑等。此外，相對於化合物[I-21]1莫耳，溶劑的使用量是0.1至300公升，佳者是0.1至100公升。 Examples of solvents 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; benzene, Aromatic hydrocarbons such as toluene, xylene, chlorobenzene; alcohols such as methanol, ethanol, 2-propanol; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl Aprotic polar solvents such as di-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone; diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkanes; water, or mixed solvents such as these. In addition, the amount of the solvent used is 0.1 to 300 liters relative to 1 mole of the compound [I-21], preferably 0.1 to 100 liters.

The reaction temperature of this reaction is usually any temperature selected from a temperature range from -30°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of 0°C to 120°C.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, reaction amount, etc., and is usually from 10 minutes to 48 hours.

After the reaction is completed, the reaction mixture is poured into water, extracted with an organic solvent, concentrated, etc., whereby the compound [I-22] can be isolated. The isolated compound [I-22] can be purified by using column chromatography, recrystallization, etc. as required.

(Step 14-3)

Examples of the azodicarboxylic acid diester that can be used in this reaction include diethyl azodicarboxylate and diisopropyl azodicarboxylate. In addition, the amount of the azodicarboxylic acid diester used is appropriately selected in the range of 1 to 10 moles relative to 1 mole of the compound [I-20], preferably 1.0 to 5.0 moles.

The amount of triphenylphosphine that can be used in this reaction is appropriately selected in the range of 1 to 10 moles relative to 1 mole of the compound [I-20], preferably 1.0 to 5.0 moles.

The use amount of the compound [XXVII] that can be used in this reaction with respect to the compound [I-20] 1 mol may be appropriately selected in the range of 1 to 10 mol, preferably 1.0 to 5.0 mol.

烷等醚類等或此等混合溶劑等。此外，相對於化合物[I-20]1莫耳，溶劑的使用量是0.1至300公升，佳者是0.1至100公升。 Examples of solvents 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; benzene, Toluene, xylene, chlorobenzene and other aromatic hydrocarbons; N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide , Cyclobutane, 1,3-dimethyl-2-imidazolidinone and other aprotic polar solvents; diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkanes or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 300 liters relative to 1 mole of the compound [I-20], preferably 0.1 to 100 liters.

The reaction temperature of this reaction is usually any temperature selected from a temperature range from -30°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of 0°C to 120°C.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, reaction amount, etc., and is usually 10 minutes to 48 hours.

After the reaction is completed, the reaction mixture is poured into water, extracted with an organic solvent, concentrated, etc., whereby the compound [I-22] can be isolated. The isolated compound [I-22] can be purified by using column chromatography, recrystallization, etc. as required.

<Manufacturing method 15>

Among the compounds of the present invention, the compound represented by the general formula [I-23] can be produced according to the following method, for example.

(In the ^{formula, L 2, R 3, R} 4, R 5, R 6, R e and n are the same meaning as aforementioned)

That is, the compound represented by the general formula [I-23] is a compound and the compound [VI] represented by the general formula [I-20] can be reacted in an appropriate solvent in the presence or absence of an appropriate base manufacture.

The base, solvent, reaction temperature and reaction time that can be used in this reaction are the same as those in Production Method 3.

After the reaction is completed, the reaction mixture is poured into water and neutralized, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to separate the compound [I-23]. The isolated compound [I-23] can be purified by using column chromatography, recrystallization, etc. as required.

<Manufacturing method 16>

Among the compounds of the present invention, the compound represented by the general formula [I-25] can be produced according to the following method, for example.

(In the formula, R ¹⁴ represents a hydrogen atom, a group C(=O)OR ¹⁰ , C ₁ to C ₆ alkyl, L ² , R ³ , R ⁴ , R ⁶ , R ⁷ , R ¹⁰ , R ^a and n represent (Same meaning as above)

That is, the compound represented by the general formula [I-25] can be produced by reacting the compound represented by the general formula [I-24] and the compound XXVIII in an appropriate solvent in the presence of a suitable base.

The use amount of the compound [XXVIII] used in the present invention may be appropriately selected in the range of 1 to 10 moles relative to 1 mole of the compound [I-24], preferably 1.0 to 3.5 moles.

Examples of the base that can be used in this 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; and sodium carbonate , Alkali carbonates such as potassium carbonate; inorganic alkalis such as alkali metal bicarbonate such as sodium bicarbonate and potassium bicarbonate; metal hydrides such as sodium hydride and potassium hydride; sodium methoxide and ethoxy Metal salts of alcohols such as sodium and potassium tributoxide or triethylamine, N,N-dimethylaniline, pyridine, 4-N,N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0]-7-undecene and other organic bases. In addition, the amount of the base used may be appropriately selected in the range of 1 to 5 moles relative to 1 mole of the compound [I-24], preferably 1.0 to 3.0 moles.

烷等醚類；苯、甲苯、二甲苯、氯苯等芳香族烴類；二氯甲烷、氯仿、1,2-二氯乙烷等鹵化烴類；N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯酮、二甲基亞碸、環丁碸、1,3-二甲基-2-咪唑啉酮等非質子性極性溶劑類；甲醇、乙醇、2-丙醇 等醇類；乙腈、丙腈等腈類；乙酸乙酯、乙酸丁酯、丙酸乙酯等酯類；戊烷、己烷、環己烷、庚烷等脂肪族烴類；吡啶、甲基吡啶等吡啶類；水或此等混合溶劑等。此外，相對於化合物[I-24]1莫耳，溶劑的使用量是0.1至100公升，佳者是0.2至10公升。 Examples of solvents that can be used in this reaction include diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-di

Ethers such as alkane; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene; halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane; N,N-dimethylformamide, Aprotic polar solvents such as N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, cyclobutane, 1,3-dimethyl-2-imidazolidinone Alcohols; methanol, ethanol, 2-propanol and other alcohols; acetonitrile, propionitrile and other nitriles; ethyl acetate, butyl acetate, ethyl propionate and other esters; pentane, hexane, cyclohexane, heptane Aliphatic hydrocarbons; pyridines such as pyridine and picoline; water or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 100 liters relative to 1 mol of the compound [I-24], preferably 0.2 to 10 liters.

The reaction temperature in this reaction may be any temperature within a range from -30°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of 0°C to 150°C.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, reaction amount, etc., and is usually 10 minutes to 24 hours.

After the reaction is completed, the reaction mixture is poured into water, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated to perform operations such as isolation of the compound [I-25]. The isolated compound [I-25] can be purified by using column chromatography, recrystallization, etc. as required.

In addition, the compound [III] and the like that belong to the intermediate for producing the compound of the present invention represented by the general formula [I] or [II] can be produced according to the production methods shown below, but it is not limited to these methods.

<Method of Manufacturing Intermediate 1>

(In the formula, R ^C represents a cyano group or a carboxyl group, and R ³ , R ⁴ , X ¹ and n represent the same meaning as described above)

That is, the compound represented by the general formula [IX] can be produced by reacting the compound [VIII] with a halogenating agent in an appropriate solvent.

Halogenating agents usable in this reaction include chlorine, sulfonyl chloride, N-chlorosuccinimide, bromine, N-bromosuccinimide, 1,3-dibromo-5,5-hydantoin , Iodine, N-iodosuccinimide, 1,3-diiodo-5,5-hydantoin, etc. In addition, the amount of halogenating agent used may be appropriately selected in the range of 0.5 to 10 moles relative to 1 mole of compound [VIII], and preferably 0.5 to 2.0 moles.

Examples of solvents 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; and acetonitrile. Nitriles such as propionitrile; carboxylic acids such as acetic acid, propionic acid, trifluoroacetic acid; sulfuric acid, water, or these mixed solvents. In addition, the amount of the solvent used is 0.1 to 300 liters relative to 1 mole of compound [VIII], preferably 0.3 to 20 liters.

The reaction temperature of this reaction is usually any temperature selected from a temperature range of -70°C to the reflux temperature of the reaction system, and it is preferably carried out in the range of -20°C to 100°C.

The reaction time of this reaction varies with the reaction temperature, reaction substrate, reaction amount, etc., and is usually 10 minutes to 24 hours.

After the reaction is completed, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated, whereby the compound [IX] can be isolated. The isolated compound [IX] can be purified by using column chromatography, recrystallization, etc. as required.

<Method of Manufacturing Intermediate 2>

(In the formula, X ² represents a hydrogen atom or a halogen atom, and B ¹ , R ³ , R ⁴ , R ⁶ and n represent the same meaning as above)

That is, the compound represented by the general formula [XV] can be used as described in Chem. Pharm. Bull., Vol. 23 (No. 5) page 955-page 966 (1975) or Japanese Patent Application Publication No. 2007-308485 Method or according to the method described (Step 2'-1) in a suitable solvent, After compound [X] is converted to compound [XI] using an acid halogenating agent in the presence or absence of a suitable catalyst, (Step 2'-2) in a suitable solvent in the presence of a suitable base or In the absence of, after compound [XI] and compound [XII] are reacted to obtain compound [XIII], (Step 2'-3) in an appropriate solvent or without solvent, in the presence of an appropriate acid, the compound [ XIII] reacts with cyanate or thiocyanate to obtain compound [XIV], (step 2'-4) in a suitable solvent in the presence of a suitable base, cyclization reaction to produce compound [XIV] .

<Method of Manufacturing Intermediate 3>

(In the formula, B, R ³ , R ⁴ , R ⁵ , R ⁶ , X ¹ and n represent the same meaning as above)

That is, the compound represented by the general formula [III-1] can be produced by reacting the compound [XVI] with a halogenating agent in an appropriate solvent.

The halogenating agent used in this reaction, the solvent usable in this reaction, the reaction temperature and the reaction time are the same as those of the intermediate production method 1.

After the reaction is completed, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to separate the compound [III-1]. The isolated compound [III-1] can be purified by using column chromatography, recrystallization, etc. as required.

<Method of Manufacturing Intermediate 4>

(Wherein, R ^{5 'represents} a C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkyl, C ₃ to C ₆ cycloalkyl, a C ₁ to C ₆ -alkyl, C ₁ to C ₆ haloalkyl, or C ₃ to C ₆ halocycloalkyl, R ^6′ represents C ₁ to C ₆ alkyl, R ^d represents C ₁ to C ₆ alkyl, L ³ represents a halogen atom, R ³ , R ⁴ , X ¹ and n represent (Same meaning as above)

That is, the compound represented by the general formula [III-4] can use the method described in Japanese Patent Application Publication No. 2007-308485 or the method according to it, (Step 4'-1) in an appropriate solvent or without In the presence of an alcohol, the compound [XVII] and hydrogen chloride are reacted by Pinner to produce the hydrochloride salt of the compound [XVIII], and then (step 4'-2) in an appropriate solvent in an appropriate base In the presence or absence of the compound, the compound [XVIII] and the hydrazine are reacted to produce the compound [XIX], further (step 4'-3) in an appropriate solvent in the presence or absence of an appropriate base, The compound [XIX] is reacted with the compound [XX] or with the compound [XXI] to produce the compound [III-3], and finally (step 4'-4) the compound [III-3] is reacted with the compound [XXII] And manufacture compound [III-4]. At this time, compound [III-4'] can be produced as a by-product.

<Method of Manufacturing Intermediate 5>

(In the formula, R ³ , R ⁴ , R ⁶ , R ¹⁰ , X ² and n represent the same meaning as above)

That is, the compound represented by the general formula [III-5] can use the method described in Tetrahedron Letters, Vol. 53, pages 6078-6082 (2012) or according to the described method, in a suitable solvent, the compound [ XIII] is produced by reacting with compound [XXV].

<Method of Manufacturing Intermediate 6>

(In the formula, R ⁶ , R ¹¹ and X ^{1 have the} same meaning as above)

That is, the compound represented by the general formula [XXIII] is a compound [XVIII] that can be prepared by using the method described in (Step 6-1) US4670448A (1987) or according to the described method in an appropriate solvent or without a solvent The compound [XXX] is reacted with the compound [XXIX] to produce the compound [XXX], and then (Step 6-2) The compound [XXX] can be produced by Sandmyer reaction in an appropriate solvent in the presence of copper halide.

The halogenating agent, usable solvent, reaction temperature and reaction time used in the reaction of Step 6-2 are the same as those of Production Method 12.

After the reaction is completed, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated, whereby the compound [XXIII] can be isolated. The isolated compound [XXIII] can be purified by using column chromatography, recrystallization, etc. as required.

The 5-(1,2,4-triazol-5-yl)benzoic acid derivative represented by the general formula [II] of the present invention or its ester form is used to produce the 5-(represented by the general formula [I] of the present invention. 1,2,4-triazol-5-yl)benzamide derivatives or compounds that are useful as intermediates in agriculturally acceptable salts.

Furthermore, the 5-phenyl-1,2,4-triazole derivative represented by the general formula [III] of the present invention is a 5-(1,2,4- represented by the general formula [II] of the present invention Triazole-5-yl)benzoic acid derivatives or their esters are useful compounds as intermediates.

The pesticide composition of the present invention contains the 5-(1,2,4-triazol-5-yl)benzamide derivative represented by the general formula [I] of the present invention or its agriculturally acceptable salt as Active ingredients.

The agricultural chemical composition of the present invention may contain additional components (carriers) that are generally used in agricultural chemical preparations as needed.

The pest control agent of the present invention contains the 5-(1,2,4-triazol-5-yl)benzamide derivative represented by the general formula [I] of the present invention or its agriculturally acceptable salt As an active ingredient. The pest control agents of the present invention are representative of insecticides, acaricides and nematicides.

The pest control agent of the present invention may contain additional components (carriers) that are usually used in pesticide preparations as needed.

Examples of the added component include carriers such as solid carriers or liquid carriers, surfactants, binders and tackifiers, tackifiers, colorants, extenders, spreading agents, antifreeze agents, anti-caking agents, and disintegration Agents, anti-decomposition agents, etc., according to other needs, preservatives and plant tablets can also be used as additional ingredients. In addition, one type of these additional components may be used, or two or more types may be used in combination.

Hereinafter, the above-mentioned added components will be described in detail.

Examples of solid carriers include pyrophyllite clay, kaolin clay, silica clay, talc, diatomaceous earth, zeolite, bentonite, acid clay, activated clay, attapulgite clay, vermiculite, and perlite , Pumice, white carbon (synthetic silicic acid, synthetic silicate, etc.), titanium dioxide and other mineral-based carriers; wood flour, corn stalks, walnut shells, fruit kernels, rice husks, sawdust, bran, soy flour, powdered cellulose , Starch, dextrin, sugar and other vegetable carriers; calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride and other inorganic salt carriers; polyethylene, polypropylene, polyvinyl chloride, polyvinyl acetate, ethylene-vinyl acetate Polymer carriers such as copolymers and urea-aldehyde resins.

烷、2-乙氧基乙醇(cellosolve)、二丙基醚、四氫呋喃等醚類；直鏈烷烴(normal paraffin)、環烷烴(naphthene)、異構烷烴(isoparaffin)、煤油、礦油等脂肪族烴類；甲苯、C₉-C₁₀烷基苯、二甲苯、溶劑石油腦(solvent naphtha)、烷基萘、高沸點芳香族烴等芳香族烴類；1,2-二氯乙烷、氯仿、四氯化碳等鹵化烴類；乙酸乙酯、苯二甲酸二異丙酯、苯二甲酸二丁酯、苯二甲酸二辛酯、己二酸二甲酯等酯類；γ-丁內酯之等內酯類；N,N-二甲基甲醯胺、N,N-二乙基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-吡咯酮等醯胺類；乙腈等腈類；二甲基亞碸等硫化合物類；大豆油、菜籽油、棉籽油、椰子油、蓖麻籽油等植物油；水等。 Examples of the liquid carrier include monohydric alcohols such as methanol, ethanol, propanol, 2-propanol, butanol, and cyclohexanol; ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, and polyethylene glycol. Polyols such as propylene 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 Class; ether, 1,4-di

Alkanes, 2-ethoxyethanol (cellosolve), dipropyl ether, tetrahydrofuran and other ethers; linear paraffins (normal paraffin), naphthene (naphthene), isoparaffin (isoparaffin), kerosene, mineral oil and other aliphatic Hydrocarbons; aromatic hydrocarbons such as toluene, C ₉ -C ₁₀ alkylbenzene, xylene, solvent naphtha, alkyl naphthalene, high-boiling aromatic hydrocarbons; 1,2-dichloroethane, chloroform , Halogenated hydrocarbons such as carbon tetrachloride; ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate and other esters; γ-butyrolene Lactones such as esters; N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, etc. Acetamides; nitriles such as acetonitrile; sulfur compounds such as dimethyl sulfoxide; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, coconut oil, castor seed oil; water, etc.

The surfactant is not particularly limited, and the one that shows gelation or swelling in water is preferred, 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 Alkylphenyl ether formalin condensate, polyoxyethylene polyoxypropylene segment copolymer, alkyl polyoxyethylene polypropylene segment copolymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty amide, polyoxyethylene Ethylene fatty acid diphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene glycol, polyoxyalkylene addition acetylene glycol, polyoxyethylene ether type poly Non-ionic surfactants such as silicone, ester-type silicone, fluorine-based surfactants, polyoxyethylene castor seed oil, polyoxyethylene hardened castor seed oil; alkyl sulfates, polyoxyethylene alkyl ethers Sulfate, polyoxyethylene alkyl phenyl ether sulfate, polyoxyethylene styryl phenyl ether sulfate, alkyl benzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonic acid Salt, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonic acid, salt of formalin condensate of alkyl naphthalene sulfonate, fatty acid salt, polycarboxylic acid Salt, N-methyl-fatty acid sarcosinate, resinate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl phenyl ether phosphate and other anionic surfactants; laurylamine hydrochloride, Stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminepropylamine acetate, alkyltrimethylammonium chloride, alkyldimethylhydroxychloroaniline, etc. Cationic surfactants such as alkylamine salts; betaine type such as dialkyldiaminoethyl betaine, alkyl dimethyl benzyl betaine, dialkylaminoethylglycine, alkyl di Amphoteric surfactants such as amino acid type such as methylbenzylglycine etc.

Examples of binding agents and tackifiers include carboxymethyl cellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, and polyacetic acid Vinyl esters, sodium polyacrylate, polyethylene glycol with an average molecular weight of 6,000 to 20,000, polyethylene oxide with an average molecular weight of 100,000 to 5 million, natural phospholipids (eg, cephalinic acid, lecithin, etc.), etc.

Examples of the thickener include xanthan gum, guar gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch derivatives, polysaccharides, and other water-soluble polymers; such as high purity Bentonite, inorganic fine powder of white carbon, etc.

Examples of the colorant include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue; organic dyes such as alizarin dye, azo dye, and metal phthalocyanine dye.

Examples of the extender include polysiloxane-based surfactants, cellulose powder, dextrin, processed starch, polyaminocarboxylic acid chelate compounds, cross-linked polyvinylpyrrolidone, maleic acid, and styrenes. , Methacrylic acid copolymers, polyhydric alcohol polymers and half esters of dicarboxylic anhydride, water-soluble salts of polystyrene sulfonic acid, etc.

Examples of the spreading agent include various surfactants such as sodium dialkyl sulfosuccinate, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene fatty acid ester; paraffin, terpene Ethylene, polyamide resin, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, synthetic resin emulsion, etc.

Examples of antifreeze agents include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.

Examples of anti-caking agents include polysaccharides such as starch, alginic acid, mannose, and galactose; polyvinylpyrrolidone, white carbon, ester gum, petroleum resin, and the like.

Examples of the disintegrant include sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, and polyaminocarboxylic acid chelate. Compounds, sulfonated styrene/isobutylene/maleic anhydride copolymer, starch/polyacrylonitrile graft copolymer, etc.

Examples of the anti-decomposition agent include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol-based, amine-based, sulfur-based, and phosphoric acid-based; ultraviolet absorbers such as salicylic acid-based and diphenyl ketone-based.

On the other hand, when the pest control agent of the present invention contains the above-mentioned added components, the addition ratio thereof is based on mass, and it is usually 5 to 95% in a solid carrier or liquid carrier, preferably 20 to 90 It is selected in the range of %, and the surfactant is usually selected in the range of 0.1% to 30%, preferably in the range of 0.5 to 10%, and other additives are selected in the range of 0.1 to 30%, preferably in the range of 0.5 to 10%.

The pest control agent of the present invention is a preparation formulated into any of the following dosage forms: powder, powder granule, granule, water and agent, water solvent, granular water and agent, lozenge, jumper agent, emulsion, Oils, liquids, flowable agents, emulsifiers, microemulsifiers, suspension emulsions (Suspoemulsion), micro-dispersants, microcapsules, fumigants, aerosols, bait agents, paste preparations, etc.

When these preparations are actually used, they can be used directly, or they can be released to a predetermined concentration with a release agent such as water. The application of various preparations containing the compound of the present invention or its alkenes is by the usual general application method, that is, by spraying (for example, spraying, atomizing, micronizing, loose powder, loose granules, water surface application, tank Application, etc.), soil application (eg, mixing, infusion, etc.), surface application (eg, coating, powder coating, coating, etc.), seed treatment (eg, painting, powder coating treatment, etc.), dipping, poison bait, fumigation application, etc. Apply. In addition, the aforementioned active ingredients may be mixed in feed and given to livestock to prevent harmful insects in their excrement, especially the generation and growth of harmful insects.

The pest control method of the present invention is derived by using 5-(1,2,4-triazol-5-yl)benzamide represented by the general formula [I] of the present invention in the aforementioned application method The amount of the active ingredient of the substance or its agriculturally acceptable salt is implemented.

The compounding ratio (mass %) of the active ingredient of the pest control agent of the present invention can be appropriately selected according to needs. For example, when it is made into powders, granules, granules, etc., it is in the range of 0.01 to 20%, preferably in the range of 0.05 to 10%, and it is preferably selected in the range of 0.05 to 10%. It is preferably selected in the range of 0.5 to 20%, and it is preferably in the range of 1 to 70% when it is made into water and agent, granular water and agent, etc. It is preferably selected in the range of 5 to 50%. When it is made into water solvent, liquid agent, etc., it is in the range of 1 to 95%, preferably in the range of 10 to 80%. It is preferably selected in the range of 10 to 80%. The range of 80% is preferably selected appropriately, when it is made into an oil agent, etc., it is 1 to 50%, and the case is preferably selected within a range of 5 to 30%, when it is made into a suspension agent, etc., it is 5 to 60. %, the better is appropriately selected in the range of 10 to 50%, preferably 5 to 70% when made into emulsifiers, microemulsifiers, suspending emulsions, etc., preferably in the range of 10 to 60% It is better to choose from 1 to 80% when making lozenges, baits, paste preparations, etc. It is better to choose properly from 5 to 50%, and from 0.1 to 80% when making fumigants etc. 50%, the better is properly selected in the range of 1 to 30%, 0.05 to 20% when made into aerosol, etc., the better is appropriately selected in the range of 0.1 to 10%.

These formulations are released or applied directly to the appropriate concentration.

The application of the pest control agent of the present invention is usually carried out at an active ingredient concentration of 0.1 to 5000 ppm when it is used as a release agent. When the preparation is directly used, the application amount per unit area is 0.1 to 5000 g per 1ha for the active ingredient compound, but it is not limited thereto.

In addition, the pest control agent of the present invention is not only effective when the compound of the present invention is used alone as an active ingredient, but can also be combined with other fertilizers and pesticides, such as insecticides, acaricides, nematicides, Effective agents, fungicides, antiviral agents, attractants, herbicides, plant growth regulators, etc. are mixed and used together, and in this case, even further excellent effects may be exhibited.

Next, exemplified well-known insecticides, acaricides, nematicides, and synergist compounds that can be mixed or used together.

Insecticidal active ingredients:

(diflovidazin)、錫滿丹(cyhexatin)、亞滅寧(cypermethrin)[包含α-體、β-體、θ-體、ζ-體]、dimpropyridaz(通用名)、二甲基-2,2,2-三氯-1-羥乙基膦酸酯(DEP)、甲基毒蟲畏(dimethylvinphos)、大滅松(dimethoate)、四氟甲醚菊酯(dimefluthrin)、矽護芬(silafluofen)、賽滅淨(cyromazine)、賜諾特(spinetoram)、賜諾殺(spinosad)、賜派芬(spirodiclofen)、賜滅派(spirotetramat)、spiropidion(通用名)、賜滅芬(spiromesifen)、速克吩鈉鹽(sulcofuron-sodium)、氟蟲胺(sulfluramid)、碸蟲啶(sulfoxaflor)、治螟磷(sulfotep)、大利松(diazinon)、賽果培(thiacloprid)、賽速安(thiamethoxam)、tioxazafen(通用名)、硫敵克(thiodicarb)、硫賜安(thiocyclam)、殺蟲雙(thiosultap)、硫磷

(thionazin)、硫伐隆(thiofanox)、硫滅松(thiometon)、tyclopyrazoflor(通用名)、四剋安勃(tetrachlorantraniliprole)、樂本松(tetrachlorvinphos)、得脫蟎(tetradifon)、氟氰蟲醯胺(tetraniliprole)、四氟醚菊酯(tetramethylfluthrin)、治滅寧(tetramethrin)、丁基嘧啶磷(tebupirimfos)、得芬諾(tebufenozide)、得芬瑞(tebufenpyrad)、汰福寧(tefluthrin)、得福隆(teflubenzuron)、滅賜松(demeton-S-methyl)、雙硫磷(temephos)、第滅寧(deltamethrin)、托福松(terbufos)、泰滅寧(tralomethrin)、拜富寧(transfluthrin)、唑蚜威(triazamate)、三落松(triazophos)、三氯松(trichlorfon)、殺蟲隆(triflumuron)、三氟苯嘧啶(triflumezopyrim)、混殺威(trimethacarb)、脫芬瑞(tolfenpyrad)、乃力松(naled)、尼古丁(nicotine)、烯啶蟲胺(nitenpyram)、尼莫克汀(nemadectin)、諾伐隆(novaluron)、諾福隆(noviflumuron)、臘蚧輪刺抱菌(Verticillium lecanii)、烯蟲乙酯(hydroprene)、液化澱粉芽孢桿菌(Bacillus amyloliquefaciens)、堅強芽孢桿菌(Bacillus firmus)、球形芽孢桿菌(Bacillus sphaericus)、枯草桿菌(Bacillus subtillis)、蘇力菌(Bacillus thuringiensis)、蘇力菌(Bacillus thuringiensis)生產的昆蟲毒素、蘇力菌相澤氏亞種(Bacillus thuringiensis subsp.Aizawai)、蘇力菌以色列亞種(Bacillus thuringiensis subsp.Israelensis)、蘇力菌庫斯克亞種(Bacillus thuringiensis subsp.Kurstaki)、蘇力菌擬步行亞種(Bacillus thuringiensis subsp.Tenebrionis)、日本甲蟲芽孢桿菌(Bacillus popilliae)、巴斯德穿刺桿菌胞子(Pasteuriapenetrans spore)、繁米松(vamidothion)、巴拉松 (parathion)、甲基巴拉松(parathion-methyl)、合芬寧(halfenprox)、合芬隆(halofenozide)、二丙烯除蟲菊酯(bioallethrin)、S-環戊烯基二丙烯除蟲菊酯(bioallethrinS-cyclopentenyl)、苄呋菊酯(bioresmethrin)、雙-(2-氯-1-甲基乙基)醚(DCIP)、雙三氟蟲脲(bistrifluron)、愛美松(hydramethylnon)必芬蟎(bifenazate)、畢芬寧(bifenthrin)、氟他胺(pyflubumide)、協力精(piperonyl butoxide)、派滅淨(pymetrozine)、白克松(pyraclofos)、派福若(pyrafluprole)、必芬松(pyridaphenthion)、畢達本(pyridaben)、三氟甲吡醚(pyridalyl)、哌氟喹腙(pyrifluquinazon)、吡普若(pyriprole)、百利普芬(pyriproxyfen)、比加普(pirimicarb)、畢汰芬(pyrimidifen)、嘧蟎胺(pyriminostrobin)、甲基亞特松(pirimiphos-methyl)、除蟲菊素(pyrethrine)、氨磺磷(famphur)、芬普尼(fipronil)、芬殺蟎(fenazaquin)、芬滅松(fenamiphos)、撲滅松(fenitrothion)、芬諾克(fenoxycarb)、芬硫克(fenothiocarb)、酚丁滅蝨(phenothrin)[包含(1R)-反式-體]、丁基滅必蝨(fenobucarb)、芬殺松(fenthion)、賽達松(phenthoate)、芬化利(fenvalerate)、芬普蟎(fenpyroximate)、芬佈賜(fenbutatin oxide)、芬普寧(fenpropathrin)、大福松(fonofos)、磺醯氟(sulfuryl fluoride)、佈嘉信(butocarboxim)、丁酮碸威(butoxycarboxim)、布芬淨(buprofezin)、呋線威(furathiocarb)、普亞列寧(prallethrin)、嘧蟎酯(fluacrypyrim)、三氟咪啶醯胺(fluazaindolizine)、克福隆(fluazuron)、氟速芬(fluensulfone)、福拜倫(fluopyram)、氟乙酸鈉鹽(sodium fluoroacetate)、fluxametamide(fluxametamide)、氟環脲 (flucycloxuron)、護賽寧(flucythrinate)、氟硫滅(flusulfamide)、賽扶寧(fluthrin)、氟胺氰菊酯(fluvalinate)[包含τ-體]、氟吡呋喃酮(flupyradifurone)、吡氟硫磷(flupyrazofos)、flupyrimin(通用名)、丁蟲腈(flufiprole)、嘧蟲胺(flufenerim)、氟菌螨酯(flufenoxystrobin)、氟芬隆(flufenoxuron)、菲殺碸(fluhexafon)、氟大滅(flubendiamide)、氟氯苯菊酯(flumethrin)、弗雷拉納(fluralaner)、氟蟲芬(flurimfen)、茉莉酮(jasmone)、順式-茉莉酮(cis-jasmone)、普硫松(prothiofos)、羅芬布(protrifenbute)、氟尼胺(flonicamid)、加護松(propaphos)、毆蟎多(propargite)、佈飛松(profenofos)、溴蟲氟苯雙醯胺(broflanilide)、四氟苯甲菊酯(profluthrin)、撲達松(propetamphos)、安丹(propoxur)、弗洛梅托昆(flometoquin)、新殺蟎(bromopropylate)、合賽多(hexythiazox)、六伏隆(hexaflumuron)、細腳擬青黴(Pacilimyces tenuipes)、玫煙色擬青黴(Paecilomyces fumosoroceus)、淡紫擬青黴菌(Paecilomyces lilacinus)、右旋七氟甲醚菊酯(heptafluthrin)、飛達松(heptenophos)、百滅寧(permethrin)、benclothiaz(benclothiaz)、benzpyrimoxan(通用名)、免速達(bensultap)、苯蟎特(benzoximate)、免敵克(bendiocarb)、免扶克(benfuracarb)、纖細白僵菌(Beauveria tenella)、巴氏蠶白僵菌(Beauveria bassiana)、布氏白僵菌(Beauveria brongniartii)、巴賽松(phoxim)、裕必松(phosalone)、福賽絕(fosthiazate)、丁硫環磷(fosthietan)、福賜米松(phosphamidon)、益滅松(phosmet)、抗蟎素複合體(polynactins)、覆滅璊(formetanate)、福瑞松(phorate)、機油 (machine oil)、馬拉松(malathion)、密滅汀(milbemectin)、滅加松(mecarbam)、倍硫磷亞碸(mesulfenfos)、納乃得(methomyl)、聚乙醛(metaldehyde)、美氟綜(metaflumizone)、達馬松(methamidophos)、威百畝(metham)、滅賜克(methiocarb)、滅大松(methidathion)、異硫氰酸甲酯(methyl isothiocyanate)、溴化甲烷(methyl bromide)、甲氧氯(methoxychlor)、滅芬諾(methoxyfenozide)、對甲氧基甲基菊酯(methothrin)、美特寧(metofluthrin)、美賜平(methoprene)、治滅蝨(metolcarb)、美文松(mevinphos)、氯氟醚菊酯(meperfluthrin)、瘤捕單頂孢菌(Monacrosporium phymatophagum)、亞素靈(monocrotophos)、沒氟菊酯(momfluorothrin)、哈氏木黴菌(Trichoderma harzianum)、夜蛾誘劑A(litlure-A)、夜蛾誘劑B(litlure-B)、磷化鋁(aluminium phosphide)、磷化鋅(zinc phosphide)、磷化氫(phosphine)、祿芬隆(lufenuron)、rescalure(紅圓蚧引誘劑)、列滅寧(resmethrin)、雷皮菌素(lepimectin)、魚藤精(rotenone)、核多角體病病毒包埋體、芬佈賜(fenbutatin oxide)、氰化鈣(calcium cyanide)、有機錫化合物(organotins)、硫酸尼古丁(nicotine-sulfate)、(Z)-11-十四烯基=乙酸酯、(Z)-11-十六碳烯醇、(Z)-11-十六碳烯基=乙酸酯、(Z)-9,12-十四碳二烯基=乙酸酯、(Z)-9-十四碳烯-1-醇、(Z,E)-9,11-十四碳二烯基=乙酸酯、(Z,E)-9,12-十四碳二烯基=乙酸酯、1,1,1-三氯-2,2-雙(4-氯苯基)乙烷(DDT)、1,3-二氯丙烯(1,3-dichloropropene)、2-氯-4-氟-5-[(5-三氟甲基硫基)戊基氧]苯基2,2,2-三氟乙基亞碸(化學名，CAS登錄號碼：1472050-04-6)、2,4-二氯-5- {2-[4-(三氟甲基)苯基]乙氧基}苯基2,2,2-三氟乙基亞碸(化學名，CAS登錄號碼：1472052-11-1)、2,4-二甲基-5-[6-(三氟甲基硫基)己氧基]苯基-2,2,2-三氟乙基亞碸(化學名，CAS登錄號碼：1472050-34-2)、2-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亞磺醯基]苯氧基}-5-(三氟甲基)吡啶(化學名，CAS登錄號碼：1448758-62-0)、3-氯-2-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亞磺醯基]苯氧基}-5-(三氟甲基)吡啶(化學名，CAS登錄號碼：1448761-28-1)、4,6-二硝基-o-甲酚(DNOC)、4-氟-2-甲基-5-(5,5-二甲基己氧基]苯基2,2,2-三氟乙基亞碸(化學名，CAS登錄號碼：1472047-71-4)、Bt蛋白質(Cry1Ab、Cry1Ac、Cry1Fa、Cry2Ab、mCry3A、Cry3Ab、Cry3Bb、Cry34/35Ab1)、CL900167(編碼序號)、NA-85(編碼序號)、NI-30(編碼序號)、O,O-二乙基-O-[4-(二甲基胺磺醯基)苯基]-硫代磷酸酯(DSP)、O-乙基-O-4-(硝基苯基)苯基硫代臉酸酯(EPN)、RU15525(編碼序號)、XMC(XMC)、Z-13-二十碳烯-10-酮、ZXI8901(編碼序號)、F4260(編碼序號)。 Anacrinthrin, azadirachtin, azamethiphos, acynonapyr (common name), azinphos-ethyl, azinphos-methyl, azinphos-methyl, Acequinocyl, acetamiprid, acetoprole, acephate, azocyclotin, abamectin, afidopyropen , Afoxolaner, amidoflumet, amitraz, alanycarb, aldicarb, aldoxycarb, allethrin [ Contains d-cis-trans-body, d-trans-body], isazophos, isamidofos, isocarbophos, isoxathion, isocycloseram (general purpose Name), isofenphos-methyl, isoprocarb, epsilon-metofluthrin, epsilon-metofluthrin (epsilon- momfluorothrin), ivermectin, imicyafos, imidacloprid, imiprothrin, indoxacarb, esfenvalerate, ethiofencarb ), ethion, ethiprole, ethylene dibromide, etoxazole, etofenprox, ethoprophos, etrimfos ), emamectin, emamectin benzoate, endosulfan, empenthrin, oxazosulfyl (common name), oxamyl, oxydemeton-methyl ), oxydeprofos, omethoate, cadusafos, κ-tefluthrin, κ-bifenthr in), karanjin, cartap, carbaryl, carbosulfan, carbofuran, γ-BHC (gamma-BHC), methall Lice (xylylcarb), quinalphos, kinoprene, chinomethionat, coumaphos, cryolite, clothianidin, kefir mite (clofentezine), chromafenozide, chlorantraniliprole, chlorethoxyfos, chlordane, chloropicrin, chlorpyrifos, chlorpyrifos-methyl ), chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chloroprallethrin, cyazypyr ), cyanophos, diafenthiuron, diamidafos, cyantraniliprole, dienochlor, cyenopyrafen, dioxabenzofos ), diofenolan, cyclaniliprole, cycloxaprid, dicrotophos, dichlofenthion, cycloprothrin, dichloro Pine (dichlorvos), dicloromezotiaz (common name), dicofol, dicyclanil, disulfoton, dinotefuran, dinobuton, chlorofluorocyanide Cyhalodiamide, cyhalothrin [containing γ-body, λ-body], cyphenothrin [containing (1R)-trans-body], cyfluthrin [containing β -Body], diflubenzuron, cyflumetofen, fluoromite

(diflovidazin), cyhexatin, cypermethrin [including α-body, β-body, θ-body, ζ-body], dimpropyridaz (common name), dimethyl-2,2, 2-trichloro-1-hydroxyethylphosphonate (DEP), dimethylvinphos, dimethoate, dimefluthrin, silafluofen, Cyromazine, spinotoram, spinosad, spirodiclofen, spirotetramat, spiropidion (common name), spiromesifen, speed Sulcofuron-sodium, sulfluramid, sulfoxaflor, sulfotep, diazinon, thiacloprid, thiamethoxam, tioxazafen (common name), thiodicarb, thiocyclam, thiosultap, thiophosphor

(thionazin), thiofanox, thiometon, tyclopyrazoflor (general name), tetrachlorantraniliprole, tetrachlorantraniliprole, tetrachlorvinphos, tetradifon, chlorfenapyr Amine (tetraniliprole), tetramethylfluthrin, tetramethrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin, Teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, tralomethrin, transfluthrin ), triazamate, triazophos, trichlorfon, triflumuron, triflumezopyrim, trimethacarb, tolfenpyrad ), naled, nicotine, nitenpyram, nemadectin, novaluron, noviflumuron, and Pseudoceras (Verticillium lecanii), hydroprene, Bacillus amyloliquefaciens, Bacillus firmus, Bacillus sphaericus, Bacillus subtillis, Bacillus thuringiensis), insect toxin produced by Bacillus thuringiensis, Bacillus thuringiensis subsp.Aizawai, Bacillus thuringiensis subsp.Israelensis, Sullicus cusca Species (Bacillus thuringiensis subsp. Kurstaki), Bacillus turingiensis subsp. (Bacillus t huringiensis subsp.Tenebrionis), Bacillus popilliae, Pasteuriapenetrans spore, vamidothion, parathion, parathion-methyl, Halfenprox, halofenozide, bioallethrin, S-cyclopentenyl dipropenyl pyrethroid (bioallethrinS-cyclopentenyl), bioresmethrin, Bis-(2-chloro-1-methylethyl) ether (DCIP), bistrifluron (bistrifluron), hydramethylnon (bifenazate), bifenthrin (bifenthrin), flutamide (pyflubumide) ), piperonyl butoxide, pymetrozine, pyraclofos, pyrafluprole, pyridaphenthion, pyridaben, pyridalyl , Pyrifluquinazon (pyrifluquinazon), pyriprole (pyriprole), pyriproxyfen (pyriproxyfen), bigipa (pirimicarb), bififen (pyrimidifen), pyrimidin (pyriminostrobin), methyl atson (pirimiphos-methyl), pyrethrine (pyrethrine), famphur, fipronil, fenazaquin, fenamiphos, fenitrothion, fenno (Fenoxycarb), fenthiocarb (fenothiocarb), phenothrin (containing (1R)-trans-body), butyl fenbicarb (fenobucarb), fenthion (fenthion), cydarson (phenthoate), fenvalerate, fenpyroximate, fenbutatin oxide, fenpropathrin, fenpropathrin, fonofos, sulfuryl fluoride, butocarboxim ), butoxycarboxi m), buprofezin, furathiocarb, prallethrin, fluacrypyrim, fluazaindolizine, fluazuron, fluazuron Fluensulfone, Fluopyram, sodium fluoroacetate, fluxametamide (fluxametamide), flucycloxuron, flucythrinate, flusulfamide, flusulfamide, and safinin (fluthrin), fluvalinate [containing τ-body], flupyradifurone, flupyrazofos, flupyrimin (common name), flufiprole, pyrimidine Flufenerim, flufenoxystrobin, flufenoxuron, fluhexafon, flubendiamide, flumethrin, fluralaner , Flurimfen, jasmone, cis-jasmone, prothiofos, protrifenbute, flonicamid, propaphos ), propargite, profenofos, broflanilide, profluthrin, propetamphos, propoxur, propofol Flometoquin, bromopropylate, hexythiazox, hexaflumuron, Pacilimyces tenuipes, Paecilomyces fumosoroceus, lilac Paecilomyces lilacinus, heptafluthrin, heptenophos, permethrin, benclothiaz (benclothiaz), benzpyrimoxan (common name), bensultap ), benzoximate, bendiocarb, benfuracarb, Beauveria tenella, Beauveria bassiana, Beauveria brongniartii), phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosmet, anti-mite complex Polynactins, formetanate, phorate, machine oil, marathon, milbemectin, mecarbam, mesulfenfos , Metomyl, metaldehyde, metaflumizone, methamidophos, metham, methiocarb, methidathion, different Methyl thiocyanate (methyl isothiocyanate), methyl bromide, methoxychlor, methoxyfenozide, methothrin, metofluthrin , Metoprene, metolcarb, mevinphos, meperfluthrin, Monacrosporium phymatophagum, monocrotophos, fluorinated Momfluorothrin, Trichoderma harzianum, Litworm A (litlure-A), Litworm B (litlure-B), aluminum phosphide, zinc phosphide (zinc) phosphide, phosphine, lufenuron, rescalure (red scale attractant), resmethrin, lepimectin, rotenone, nuclear polygon Embryo of body disease virus, fenbutatin oxide, calcium cyanid e), organotins, nicotine-sulfate, (Z)-11-tetradecenyl=acetate, (Z)-11-hexadecenol, (Z)-11 -Hexadecenyl=acetate, (Z)-9,12-tetradecadienyl=acetate, (Z)-9-tetradecen-1-ol, (Z,E) -9,11-tetradecadienyl=acetate, (Z,E)-9,12-tetradecadienyl=acetate, 1,1,1-trichloro-2,2- Bis(4-chlorophenyl)ethane (DDT), 1,3-dichloropropene (1,3-dichloropropene), 2-chloro-4-fluoro-5-[(5-trifluoromethylthio) Amyloxy]phenyl 2,2,2-trifluoroethyl sulfoxide (chemical name, CAS registration number: 1472050-04-6), 2,4-dichloro-5- {2-[4-(tri (Fluoromethyl)phenyl]ethoxy}phenyl 2,2,2-trifluoroethyl sulfoxide (chemical name, CAS registration number: 1472052-11-1), 2,4-dimethyl-5- [6-(trifluoromethylthio)hexyloxy]phenyl-2,2,2-trifluoroethyl sulfoxide (chemical name, CAS registration number: 1472050-34-2), 2-{2- Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenoxy}-5-(trifluoromethyl)pyridine (chemical name, CAS registration number: 1448758 -62-0), 3-chloro-2-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenoxy}-5-( Trifluoromethyl)pyridine (chemical name, CAS registration number: 1448761-28-1), 4,6-dinitro-o-cresol (DNOC), 4-fluoro-2-methyl-5-(5 ,5-dimethylhexyloxy]phenyl 2,2,2-trifluoroethyl sulfoxide (chemical name, CAS registration number: 1472047-71-4), Bt protein (Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1), CL900167 (coding serial number), NA-85 (coding serial number), NI-30 (coding serial number), O,O-diethyl-O-(4-(dimethyl Sulfamoyl)phenyl]-thiophosphoric acid ester (DSP), O-ethyl-O-4-(nitrophenyl) phenyl thiophosphonate (EPN), RU15525 (coding number), XMC (XMC), Z-13-eicosene-10-one, ZXI8901 (coding serial number), F4260 (coding serial number).

Next, exemplified well-known fungicides or disease control compound compounds that can be mixed or used together.

Bactericidal active ingredients:

咪唑反丁烯二酸鹽(oxpoconazole-fumarate)、歐索林酸(oxolinic acid)、二辛酸銅(copper dioctanoate)、辛異噻啉酮(octhilinone)、呋醯胺(ofurace)、肟醚菌胺(orysastrobin)、鄰苯基苯酚(o-phenylphenol)、嘉賜黴素(kasugamycin)、四氯丹(captafol)、加普胺(carpropamid)、加保扶(carbendazim)、嘉保信(carboxin)、香旱芹酮(carvone)、快諾芬(quinoxyfen)、quinofumelin(通用名)、蟎離丹(chinomethionat)、蓋普丹(captan)、喹康唑(quinconazole)、五氯硝苯(quintozene)、雙胍鹽(guazatine)、銅合浦單劑(cufraneb)、甲香菌酯(coumethoxystrobin)、丁香菌酯.(coumoxystrobin)、克收欣(kresoxim-methyl)、抑霉胺(clozylacon)、克氯得(chlozolinate)、四氯異苯腈(chlorothalonil)、地茂散(chloroneb)、賽座滅 (cyazofamid)、乙霉威(diethofencarb)、雙氯氰菌胺(diclocymet)、益發靈(dichlofluanid)、diehlobentiazox(通用名)、達滅淨(diclomezine)、大克爛(dicloran)、雙氯酚(dichlorophen)、二氰蒽醌(dithianon)、達克利(diniconazole)、達克利-M(diniconazole-M)、鋅乃浦(zineb)、白粉克(dinocap)、dipymetitrone(dipymetitrone)、二苯基胺(diphenylamine)、二待克利(difenoconazole)、賽芬胺(cyflufenamid)、二氟林(diflumetorim)、環克座(cyproconazole)、賽普洛(cyprodinil)、硅氟唑(simeconazole)、二甲嘧酚(dimethirimol)、二硫二甲烷(dimethyl disulfide)、達滅芬(dimethomorph)、克絕(cymoxanil)、醚菌胺(dimoxystrobin)、霍氏假單胞菌HAI-0804(Pseudomonas rhodesiae HAI-0804)、吉闌(ziram)、硅噻菌胺(silthiofam)、鏈黴素(streptomycin)、螺環菌胺(spiroxamine)、先正達(sedaxane)、座賽胺(zoxamide)、苯並烯氟菌唑(solatenol)、邁隆(dazomet)、黃藍狀菌(Talaromyces flavus)、噻醯菌胺(tiadinil)、腐絕(thiabendazole)、福美雙(thiram)、多保淨(thiophanate)、甲基多保淨(thiophanate-methyl)、賽氟滅(thifluzamide)、福美雙(thiram)、四氯硝基苯(tecnazene)、克枯爛(tecloftalam)、四克利(tetraeonazole)、咪菌威(debacarb)、得克利(tebuconazole)、氟硅唑(tebufloquin)、療黴舒(terbinafine)、多寧(dodine)、嗎菌靈(dodemorph)、三泰隆(triadimenol)、三泰芬(triadimefon)、咪唑

(triazoxide)、水楊菌胺(trichlamide)、氯啶菌酯(triclopyricarb)、深綠木霉(Trichoderma atroviride)、三賽唑(tricyclazole)、滅菌唑 (triticonazole)、三得芬(tridemorph)、賽福座(triflumizole)三氟敏(trifloxystrobin)、賽福寧(triforine)、甲基益發靈(tolylfluanid)、脫克松(tolclofos-methyl)、甲磺菌胺(tolnifanide)、托普洛卡(tolprocarb)、代森鈉(nabam)、納他黴素(natamycin)、萘替芬(naftifine)、氯草定(nitrapyrin)、酞菌酯(nitrothal-isopropyl)、尼瑞莫(nuarimol)、壬基酚磺酸銅(copper nonyl phenol sulphonate)、枯草桿菌(Bacillus subtilis)(菌株：Q ST 713)、維利黴素(validamycin)、伐利芬(valifenalate)、皮卡布西(picarbutrazox)、聯苯吡菌胺(bixafen)、啶氧菌酯(picoxystrobin)、pydiflumetofen(通用名)、比多農(bitertanol)、樂殺蟎(binapacryl)、β-檜酚酮(hinokitiol)、聯苯(biphenyl)、哌丙靈(piperalin)、殺紋寧(hymexazol)、唑菌酯(pyraoxystrobin)、百克敏(pyraclostrobin)、pyraziflumid(通用名)、白粉松(pyrazophos)、pyrapropoyne(通用名)、唑胺菌酯(pyrametostrobin)、pyriofenone(通用名)、啶菌

唑(pyrisoxazole)、氟醚菌醯胺(pyridachlometyl)、比芬諾(pyrifenox)、稗草畏(pyributicarb)、吡菌苯威(pyribencarb)、派美尼(pyrimethanil)、百快隆(pyroquilon)、免克寧(vinclozolin)、福美鐵(ferbam)、凡殺同(famoxadone)、吩

氧化物(phenazine oxide)、咪唑菌酮(fenamidone)、烯肟菌胺(fenaminstrobin)、芬瑞莫(fenarimol)、芬諾尼(fenoxanil)、富米綜(ferimzone)、拌種咯(fenpiclonil)、fenpicoxamid(通用名)、胺苯吡菌酮(fenpyrazamine)、芬克座(fenbuconazole)、甲呋醯胺(fenfuram)、苯銹啶(fenpropidin)、芬普福(fenpropimorph)、環菌胺 (fenhexamid)、福爾培(folpet)、熱必斯(phthalide)、布瑞莫(bupirimate)、麥穗靈(fuberidazole)、滅瘟素-S(blasticidin-S)、福拉比(furametpyr)、呋霜靈(furalaxyl)、呋喃羧酸(furancarboxylic acid)、呋霜靈(fluazinam)、氟茚唑菌胺(fluindapyr)、氟嘧菌酯(fluoxastrobin)、fluoxapiprolin(通用名)、氟比來(fluopicolide)、氟醚菌醯胺(fluopimomide)、福拜倫(fluopyram)、氟氯菌核利(fluoroimide)、福賽斯(fluxapyroxad)、氟喹唑(fluquinconazole)、氟康唑(furconazole)、順式氟康唑(furconazole-cis)、護汰寧(fludioxonil)、護矽得(flusilazole)、氟硫滅(flusulfamide)、氟噻唑(flutianil)、福多寧(flutolanil)、護汰芬(flutriafol)、氟菌蟎酯(flufenoxystrobin)、氟醯菌胺(flumetover)、氟嗎啉(flumorph)、普快淨(proquinazid)、撲克拉(prochloraz)、撲滅寧(procymidone)、硫菌威(prothiocarb)、丙硫菌唑(prothioconazole)、溴硝丙二醇(bronopol)、普拔克鹽酸鹽(propamocarb-hydrochloride)、普克利(propiconazole)、丙森鋅(propineb)、撲殺熱(probenazole)、溴克座(bromuconazole)、氟美多喹(flometoquin)、florylpicoxamid(通用名)、菲克利(hexaconazole)、本達樂(benalaxyl)、本達樂M(benalaxyl-M)、麥銹靈(benodanil)、苯菌靈(benomyl)、披扶座(pefurazoate)、平克座(penconazole)、賓克隆(pencycuron)、苯并烯氟菌唑(benzovindiflupyr)、佈生(benthiazole)、苯噻菌胺(benthiavalicarb-isopropyl)、吡噻菌胺(penthiopyrad)、平氟芬(penflufen)、白克列(boscalid)、福賽得(fosetyl)(alminium，calcium，sodium)、多抗霉素(polyoxin)、福代鋅(polycarbamate)、 波爾多液(Bordeaux mixture)、代森錳銅(mancopper)、鋅錳乃浦(mancozeb)、曼普胺(mandipropamid)、滿得賓(mandestrobin)、錳乃浦(maneb)、邁克尼(myclobutanil)、礦油(mineral oils)、米多霉素(mildiomycin)、滅速克(methasulfocarb)、威百畝(metam)、右滅達樂(metalaxyl)、右滅達樂M(metalaxyl-M)、代森聯(metiram)、metyltetraprole(通用名，苯基吡唑類)、滅特座(metconazole)、苯氧菌胺(metominostrobin)、滅芬農(metrafenone)、滅派林(mepanipyrim)、氯氟醚菌唑(mefentrifluconazole)、敵蟎普(meptyldinocap)、滅普寧(mepronil)、碘克(iodocarb)、海帶多醣(laminarin)、葡萄根瘤菌(Rhizobium vitis)、亞磷酸及鹽(phosphorous acid and salts)、鹼性氯化銅(copper oxychloride)、銀(silver)、氧化亞銅(cuprous oxide)、氫氧化銅(copper hydroxide)、碳酸氫鉀(potassium bicarbonate)、碳酸氫鈉(sodium bicarbonate)、硫(sulfur)、硫酸羥基喹啉(oxyquinoline sulfate)、硫酸銅(copper sulfate)、(3,4-二氯異噻唑-5-基)甲基4-(第三丁基)苯甲酸酯(化學名，CAS登錄號碼：1231214-23-5)、BAF-045(編碼序號)、BAG-010(編碼序號)、UK-2A(編碼序號)、十二烷基苯磺酸雙乙烯二胺銅錯鹽[II](DBEDC)、MIF-1002(編碼序號)、NF-180(編碼序號)、乙酸三苯基錫(TPTA)、三苯基氯化錫(TPTC)、氫氧化三苯基錫(TPTH)、非病原性Erwinia carotovora，F9650(編碼序號)。 Azaconazole, acibenzolar-S-methyl, azoxystrobin, anilazine, anisulbrom, aminopyrifen (common name) , Ametoctradin, aldimorph, isotianil, isopyrazam, isofetamid, isoflucypram, and aci Isoprothiolane, ipconazole, ipflufenoquin (common name), ipfentrifluconazole (common name), iprodione, iprovalicarb, iprobenfos, iprobenfos, imazalil ), iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, inpyrfluxam (common name), imprimatin A (plant immune inducing compound), imprimatin B (plant immune triggering compound), edifenphos, etaconazole, ethaboxam, ethirimol, ethoxyquin, and etridiazole ), enestroburin, enoxastrobin, epoxiconazole, organic oils, oxadixyl, oxazinylazole, oxseprine (oxathiapiprolin), oxycarboxin, oxine-copper, oxytetracycline,

Oxpoconazole-fumarate, oxolinic acid, copper dioctanoate, octhilinone, octhilinone, ofurace, and oxamid (orysastrobin), o-phenylphenol, kasugamycin, captafol, carpropamid, carbendazim, carboxin, incense Carvone, quinoxyfen, quinofumelin (common name), chinomethionat, captan, quinconazole, quintozene, biguanide (guazatine), cufraneb, coumethoxystrobin, syringamate (coumoxystrobin), kresoxim-methyl, clozylacon, chlozolinate , Chlorothalonil, chloroneb, cyazofamid, diethofencarb, diclocymet, dichlofluanid, diehlobentiazox (common name) ), diclomezine, dicloran, dichlorophen, dithianon, diniconazole, diniconazole-M, zinc naipura (zineb), dinocap, dipymetitrone (dipymetitrone), diphenylamine (diphenylamine), diphennoconazole (difenoconazole), cyflufenamid, diflumetorim, cyproconazole , Cyprodinil, simeconazole, dimethirimol, dimethyl disulfide, dimethomorph, cymoxanil, dimoxystrobin ), Pseudomonas holsteinii HAI -0804 (Pseudomonas rhodesiae HAI-0804), ziram, silthiofam, streptomycin, spiroxamine, sedaxane, zetoxamine ( zoxamide), solatenol, dazomet, Talaromyces flavus, tiadinil, thiabendazole, thiram, and polyphenol Thiophanate, thiophanate-methyl, thifluzamide, thiram, thiram, tecnazene, tecloftalam, tetraeonazole , Debacarb, tebuconazole, tebufloquin, terbinafine, dodine, dodemorph, triadimenol, tritaifen (triadimefon), imidazole

(triazoxide), trichlamide, triclopyricarb, Trichoderma atroviride, tricyclazole, trigononazole, tridmorph Triflumizole trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolnifanide, tolprocarb ), nabam, natamycin, naftifine, nitrapyrin, nitrothal-isopropyl, nuarimol, nonylphenol Copper nonyl phenol sulphonate, Bacillus subtilis (strain: Q ST 713), viridamycin, valifenalate, picarbutrazox, bifenpyr Bixafen, picoxystrobin, pydiflumetofen (common name), bitertanol, binapacryl, β-hinokitiol, biphenyl, piperapron Piperalin, hymexazol, pyraoxystrobin, pyraclostrobin, pyraziflumid (common name), pyrazophos, pyrapropoyne (common name), pyramethostrobin (pyrametostrobin) , Pyriofenone (common name), cyprodin

Pyrisoxazole, pyridachlometyl, pyrifenox, pyributicarb, pyrribencarb, pyrimethanil, pyroquilon, Vinclozolin, ferbam, famoxadone, phen

Oxide (phenazine oxide), fenamidone, fenaminstrobin, fenarimol, fenoxanil, ferimzone, fenpiclonil, fenpicoxamid (common name), fenpyrazamine, fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid , Folpet, phthalide, bupirimate, fuberidazole, blasticidin-S, furametpyr, furaxyl (furalaxyl), furancarboxylic acid, fluazinam, fluindapyr, fluoxastrobin, fluoxapiprolin (common name), fluopicolide, fluorine Fluopimomide, fluopyram, fluoroimide, fluxapyroxad, fluquinconazole, fluconconazole, cisfluconazole (furconazole-cis), fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fludioxol Flufenoxystrobin, flumetover, flumorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole (prothioconazole), bronopol, propamocarb-hydrochloride, propiconazole, propineb, probenazole, bromuconazole, fluorine Flometoquin, florylpicox amid (common name), hexaconazole, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, Penconazole, pencycuron, benzovindiflupyr, benthiazole, benthiavalicarb-isopropyl, penthiopyrad, penflufen (penflufen), boscalid, fosetyl (alminium, calcium, sodium), polyoxin, polycarbamate, Bordeaux mixture, mancozeb Copper, mancozeb, mancozeb, mandipropamid, mandestrobin, maneb, myclobutanil, mineral oils, and mildew Mildiomycin, methasulfocarb, metam, metalaxyl, metalaxyl-M, metiram, metyltetraprole (common name, (Phenylpyrazoles), metconazole, metominostrobin, metrafenone, mepanipyrim, mefentrifluconazole, mepteridinocap ), mepronil, iodocarb, laminin, Rhizobium vitis, phosphorous acid and salts, copper oxychloride, silver (silver), cuprous oxide, copper hydroxide, potassium bicarbonate, sodium bicarbonate, sulfur, oxyquinoline sulfate, Copper sulfa te), (3,4-dichloroisothiazol-5-yl)methyl 4-(third butyl)benzoate (chemical name, CAS registration number: 1231214-23-5), BAF-045( (Code No.), BAG-010 (Code No.), UK-2A (Code No.), dodecylbenzenesulfonic acid diethylenediamine copper salt [II] (DBEDC), MIF-1002 (Code No.), NF -180 (coding number), triphenyltin acetate (TPTA), triphenyltin chloride (TPTC), triphenyltin hydroxide (TPTH), non-pathogenic Erwinia carotovora, F9650 (coding number).

Next, the known herbicide compounds and plant growth regulator compounds that can be mixed or used together are exemplified as follows.

Herbicidal active ingredients:

氯草酮(isoxachlortole)、異

唑草酮(isoxaflutole)、伊索本(isoxaben)、異癸醇乙氧基化物(Isodecylalkoholethoxylate)、異丙隆(isoproturon)、三唑醯草胺(ipfencarbazone)、滅草喹(imazaquin)、甲基咪草煙(imazapic)(包含胺等鹽)、依滅草(imazapyr)(包含異丙胺等鹽)、甲基咪草酸(imazamethabenz-methyl)、甲氧咪草煙(imazamox)、咪草烟(imazethapyr)、依速隆(imazosulfuron)、茚

氟草胺(indaziflam)、茚草酮(indanofan)、甘草津(eglinazine-ethyl)、禾草畏(esprocarb)、甲磺隆(ethametsulfuro正methyl)、乙丁烯氟靈(ethalfluralin)、磺噻隆(ethidimuron)、亞速隆(ethoxysulfuron)、氯氟草醚乙酯(ethoxyfen-ethyl)、益覆滅(ethofumesate)、乙氧苯草胺(etobenzanid)、草藻滅(endothal-disodium)、樂滅草(oxadiazon)、丙炔

草酮(oxadiargyl)、

草酮(oxaziclomefone)、環氧嘧磺隆(oxasulfuron)、復祿芬(oxyfluorfen)、歐拉靈(oryzalin)、嘧苯胺磺隆(orthosulfamuron)、坪草丹(orbencarb)、油酸(oleic acid)、苯酮唑 (cafenstrole)、乙基克繁草(carfentrazone-ethyl)、特胺靈(karbutilate)、卡草胺(carbetamide)、快伏草(quizalofop)、快伏草(quizalofop-ethyl)、快伏草(quizalofop-P-ethyl)、喹禾糠酯(quizalofop-P-tefuryl)、莫克草(quinoclamine)、二氯喹啉酸(quinclorac)、氯甲喹啉酸(quinmerac)、苄草隆(cumyluron)、氯醯草膦(clacyfos)、嘉磷塞(glyphosate)(包含鈉、鉀、胺、丙基胺、異丙胺、二甲基胺或三甲基硫等鹽)、固殺草(glufosinate)(胺或鈉等鹽包含)、固殺草P(glufosinate-P)、固殺草P鈉鹽(glufosinate-P-sodium)、剋草同(clethodim)、clodinafop-炔丙基(clodinafop-propargyl)、畢克草(clopyralid)、可滅蹤(clomazone)、甲氧基護谷(chlomethoxyfen)、克普草(clomeprop)、氯酯磺草胺(cloransulam-methyl)、草滅平(chloramben)、殺草敏(chloridazon)、氯嘧磺隆(chlorimuron-ethyl)、氯磺隆(chlorsulfuron)、氯酸二甲酯(chlorthal-dimethyl)、草克樂(chlorthiamid)、氯醯亞胺(chlorphthalim)、整形素(chlorflurenol-methyl)、克普芬(chlorpropham)、氯溴隆(chlorbromuron)、枯草隆(chloroxuron)、綠麥隆(chlorotoluron)、ketospiradox(ketospiradox)(包含鈉、鈣或銨等鹽)、苯嘧磺草胺(saflufenacil)、假蒟亭鹼(sarmentine)、氰乃淨(cyanazine)、氰胺(cyanamide)、達有龍(diuron)、乙醯甲草胺(diethatyl-ethyl)、麥草畏(dicamba)(包含胺、二乙胺、異丙胺、二甘醇胺、鈉或鋰等鹽)、草滅特(cycloate)、環殺草(cycloxydim)、雙氯磺草安(diclosulam)、環磺隆(cyclosulfamuron)、cyclopyranil(通用名，吡唑類除草劑)、cyclopyrimorate(通用名)、敵草腈(dichlobenil)、禾草 靈(diclofop-P-methyl)、禾草靈(diclofop-methyl)、2,4滴丙酸鹽(dichlorprop)、2,4滴丙酸鹽-P(dichlorprop-P)、敵草快(diquat)、汰硫草(dithiopyr)、環草隆(siduron)、達乃安(dinitramine)、吲哚酮草酯(cinidon-ethyl)、醚磺隆(西速隆)(cinosulfuron)、達諾殺(dinoseb)、特垃酚(dinoterb)、氰氟草酯(cyhalofop-butyl)、大芬滅(diphenamid)、野燕枯(difenzoquat)、吡氟草胺(diflufenican)、二氟吡隆(diflufenzopyr)、草滅淨(simazine)、莫多草(dimethachlor)、愛落殺(dimethametryn)、汰草滅(dimethenamid)、汰草滅P(dimethenamid-P)、西草淨(simetryn)、哌草丹(dimepiperate)、

唑隆(dimefuron)、環庚草醚(cinmethylin)、滅草靈(swep)、磺草酮(sulcotrione)、甲磺草胺(sulfentrazone)、草硫膦(sulfosate)、磺醯磺隆(sulfosulfuron)、甲嘧磺隆(sulfometuron-methyl)、西殺草(sethoxydim)、特草定(terbacil)、汰草龍(daimuron)、thaxtomin A(通用名)、茅草枯(dalapon)、噻草定(thiazopyr)、氟丙嘧草酯(tiafenacil)、噻酮磺隆(thiencarbazone)(包含鈉鹽、甲基酯等)、仲草(tiocarbazil)、禾草丹(thiobencarb)、噻苯隆(thidiazimin)、噻苯隆(thidiazuron)、甲基噻吩磺隆(thifensulfuron-methyl)、甜菜胺(desmedipham)、敵草淨(desmetryne)、tetflupyrolimet(通用名)、欣克草(thenylchlor)、牧草胺(tebutam)、特丁噻草隆(tebuthiuron)、得殺草(tepraloxydim)、特糠酯酮(tefuryltrione)、特丁津(terbuthylazine)、去草淨(terbutryn)、特丁通(terbumeton)、環磺酮(tembotrione)、苯唑草酮(topramezone)、肟草酮(tralkoxydim)、三

氟草胺(triaziflam)、醚苯磺隆(triasulfuron)、氟酮磺草胺(triafamone)、野麥畏(tri-allate)、草達津(trietazine)、綠草定(triclopyr)、三氯比(triclopyr-butotyl)、三氟甲磺隆(tritosulfuron)、trifludimoxazin(通用名)、氟胺磺隆(triflusulfuron-methyl)、氟樂靈(trifluralin)、三氟啶磺隆鈉鹽(trifloxysulfuron-sodium)、苯磺隆(tribenuron-methyl)、tolpyralate(tolpyralate)、鈉得爛(naptalam)(包含鈉等鹽)、萘丙胺(naproanilide)、敵草胺(napropamide)、滅落脫(napropamide-M)、烟嘧磺隆(nicosulfuron)、草不隆(neburon)、氟草敏(norflurazon)、滅草猛(vernolate)、巴拉刈二氯鹽(paraquat dichloride)、氟氯吡啶酯(halauxifen-benzyl)、氟氯吡啶酯(halauxifen-methyl)、甲基合氯氟(haloxyfop)、甲基合氯氟(haloxyfop-P)、吡氟甲禾靈(haloxyfop-etotyl)、氟硝磺醯胺(halosafen)、氯吡嘧磺隆(halosulfuron-methyl)、bixlozone(bixlozone)、畢克爛(picloram)、氟吡醯草胺(picolinafen)、氟吡草酮(bicyclopyrone)、雙草醚(bispyribac-sodium)、唑啉草酯(pinoxaden)、必芬諾(bifenox)、哌草磷(piperophos)、雙唑草腈(pyraclonil)、磺醯草吡唑(pyrasulfotole)、芐草唑(pyrazoxyfen)、百速隆(pyrazosulfuron-ethyl)、苄草唑(pyrazolynate)、雙丙胺磷(bilanafos)、派芬草(pyraflufen-ethyl)、氯苯噠醇(pyridafol)、嘧硫草醚(pyrithiobac-sodium)、必汰草(pyridate)、環酯草醚(pyriftalid)、稗草畏(pyributicarb)、嘧啶肟草醚(pyribenzoxim)、pyrimisulfan(pyrimisulfan)、甲基嘧草醚(pyriminobac-methyl)、碸吡草唑(pyroxasulfone)、甲氧磺草胺 (pyroxsulam)、棉胺寧(phenisopham)、非草隆(fenuron)、fenoxasulfone(通用名)、

唑禾草靈(fenoxaprop)(包含甲基、乙基、異丙基酯)、精

唑禾草靈(fenoxaprop-P)(包含甲基、乙基、異丙基酯)、fenquinotrione(通用名)、噻唑禾草靈(fenthiaprop-ethyl)、四唑醯草胺(fentrazamide)、甜菜寧(phenmedipham)、丁基拉草(butachlor)、布芬草(butafenacil)、丁胺磷(butamifos)、丁酸酯(butylate)、丁烯草胺(butenachlor)、比達寧(butralin)、丁苯草酮(butroxydim)、伏速隆(flazasulfuron)、麥草氟(flamprop)(包含甲基、乙基、異丙基酯)、麥草氟M(flamprop-M)(包含甲基、乙基、異丙基酯)、甲基氟嘧磺隆(primisulfuro正methyl)、伏寄普(fluazifop-butyl)、伏寄普(fluazifop-P-butyl)、異丙吡草酯(fluazolate)、伏草隆(fluometuron)、乙羧氟草醚(fluoroglycofe正ethyl)、氟酮磺隆鈉鹽(flucarbazone-sodium)、氟消草(fluchloralin)、氟吡磺隆(flucetosulfuron)、

草酸甲酯(fluthiacet-methyl)、氟啶嘧磺隆(flupyrsulfuro正methyl)(包含鈉、鈣或銨等鹽)、氟噻草胺(flufenacet)、氟嗒

草酯(flufenpyr-ethyl)、氟丙酸酯(flupropanate)、氟洛普塞(flupoxame)、丙炔氟草胺(flumioxazin)、氟烯草酸(flumiclorac-pentyl)、唑嘧磺草胺(flumetsulam)、氟啶草酮(fluridone)、呋草酮(flurtamone)、氟氯比(fluroxypyr)(包含丁基甲酯、甲基庚酯等酯體，鈉、鈣或銨等鹽)、氟咯草酮(flurochloridone)、普拉草(pretilachlor)、甲基苄肼鈉鹽(procarbazone-sodium)、胺氟樂靈(prodiamine)、氟磺隆(prosulfuron)、芐草丹(prosulfocarb)、普拔草(propaquizafop)、毒 草安(propachlor)、普拔根(propazine)、除草靈(propanil)、拿草特(propyzamide)、異丙草胺(propisochlor)、丙

嘧磺隆(propyrisulfuron)、苯胺靈(propham)、氟唑草胺(profluazol)、調環酸鈣(prohexadione-calcium)、丙苯磺隆(propoxycarbazone)、丙苯磺隆(propoxycarbazone-sodium)、環苯草酮(profoxydim)、除草定(bromacil)、溴殺草敏(brompyrazon)、撲草淨(prometryn)、撲滅通(prometon)、溴苯腈(bromoxynil)(包含丁酸、辛酸或庚酸等酯體)、殺草全(bromofenoxim)、溴芬諾(bromobutide)、雙氟磺草胺(florasulam)、氯氟吡啶酯(florpyrauxifen)、氯氟吡啶酯(florpyrauxifen-benzyl)、菲殺淨(hexazinone)烯草胺(pethoxamid)、草除靈(benazolin)、平速爛(penoxsulam)、heptamaloxyloglucan(heptamaloxyloglucan)、氟丁醯草胺(beflubutamid)、氟丁醯草胺-M(beflubutamid-M)、丁烯酸苯酯(pebulate)、壬酸(pelargonic acid)、茚蟲威(bencarbazone)、施得圃(pendimethalin)、雙苯嘧草酮(benzfendizone)、地散磷(bensulide)、免速隆(bensulfuron-methyl)、苯并雙環酮(benzobicyclon)、吡草酮(benzofenap)、滅草松(bentazone)、蔬草滅(pentanochlor)、環戊惡草酮(pentoxazone)、倍尼芬(benfluralin)、呋草黃(benfuresate)、殺木膦(fosamine)、氟磺胺草醚(fomesafen)、甲醯胺磺隆(foramsulfuron)、氯吡苯脲(forchlorfenuron)、2-甲基-4氯丙酸(mecoprop)(包含鈉、鉀、異丙胺、三乙醇胺、二甲基胺等鹽)、高甲氯丙酸鉀鹽(mecoprop-P-potassium)、甲磺胺磺窿(mesosulfuron)(包含甲酯等酯體)、硝磺草酮(mesotrione)、滅草胺(metazachlor)、

吡嘧磺隆(metazosulfuron)、噻唑隆(methabenzthiazuron)、苯

草酮(metamitron)、

唑醯草胺(metamifop)、威百畝(metam)、甲基砷酸二鈉(DSMA)、methiozolin(通用名)、滅草隆(methyldymuron)、甲氧隆(metoxuron)、磺草唑胺(metosulam)、甲磺隆(metsulfuron-methyl)、撲奪草(metobromuron)、甲氧苯草隆(metobenzuron)、莫多草(metolachlor)、滅必淨(metribuzin)、縮節胺(mepiquat chloride)、滅芬草(mefenacet)、單嘧磺隆(monosulfuron)(包含甲基、乙基、異丙基酯)、氯谷隆(monolinuron)、禾草敵(molinate)、碘磺隆(iodosulfuron)、甲基二磺隆鈉鹽(iodosulfulon-methyl-sodium)、iofensulfuron(iofensulfuron)、鵬橫隆-乙基鈉(iofensulfuron-sodium)、乳氟禾草靈(lactofen)、lancotrione(通用名)、理有龍(linuron)、碸嘧磺隆(rimsulfuron)、環草定(lenacil)、2,2,2-三氯乙酸(TCA)(包含鈉、鈣或銨等鹽)、2,3,6-三氯苯甲酸(2,3,6-TBA)、2,4,5-三氯苯氧基乙酸(2,4,5-T)、2,4-二氯苯氧基乙酸(2,4-D)(包含胺、二乙胺、三乙醇胺、異丙胺、鈉或鋰等鹽)、2-胺基-3-氯-1,4-萘醌(ACN)、2-甲基-4-氯苯氧基乙酸(MCPA)(包含鈉鹽、乙基酯等)、2-甲基-4-氯苯氧基丁酸(MCPB)(包含鈉鹽、乙基酯等)、4-(2,4-二氯苯氧基)丁酸(2,4-DB)、4,6-二硝基-O-甲酚(DNOC)(包含胺或鈉等鹽)、AE-F-150944(編碼序號)、IR-6396(編碼序號)、MCPA硫基乙基(MCPA-thioethyl)、SYP-298(編碼序號)、SYP-300(編碼序號)、S-乙基二丙基硫基胺甲酸酯(EPTC)、S-莫多草(S-metolachlor)、S-9750(編碼序號)、MSMA(MSMA)、HW-02(編碼序號)、NC-653(編碼序號)、S-523(編碼序號)、SL-1201(編碼序號)。 Ioxynil, aclonifen, acrolein, azafenidin, acifluorfen (including sodium and other salts), azimsulfuron, azimsulfuron, Asulam, acetochlor, atrazine, anilofos, amicarbazone, amidosulfuron, amtrole, Aminocyclopyrachlor, aminopyralid, amiprofos-methyl, ametryn, alachlor, alloxydim, cypropyrimidine Alcohol (ancymidol), isouron, different

Chlorfenone (isoxachlortole), iso

Isoxaflutole, isoxaben, Isodecylalkoholethoxylate, isoproturon, ipfencarbazone, imazaquin, methyl Imazapic (containing salts such as amine), imazapyr (containing salts such as isopropylamine), imazamethabenz-methyl, imazamox, imazamox (imazamox) imazethapyr), imazosulfuron, indene

Indaziflam, indanofan, eglinazine-ethyl, esprocarb, ethametsulfuro-methyl, ethalfluralin, sulfathion (ethidimuron), ethoxysulfuron, ethoxyfen-ethyl, ethofumesate, etobenzanid, endothal-disodium, lemethamate (oxadiazon), propyne

Oxadiargyl,

Oxaziclomefone, oxasulfuron, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb, oleic acid , Cafenstrole, carfentrazone-ethyl, carbutilate, carbetamide, carbetamide, quizalofop, quizalofop-ethyl, fast Quizalofop-P-ethyl, quizalofop-P-tefuryl, quinoclamine, quinclorac, quinmerac, bensulfuron-methyl (quinmerac) cumyluron), clacyfos, glyphosate (containing sodium, potassium, amine, propylamine, isopropylamine, dimethylamine or trimethylsulfide), glufosinate ) (Including salts such as amine or sodium), glufosinate-P, glufosinate-P-sodium, clethodim, clodinafop-propargyl ), clopyralid, clomazone, chlomethoxyfen, clomeprop, cloransulam-methyl, chloramben, Chloridazon, chlorimuron-ethyl, chlorsulfuron, chlorthal-dimethyl, chlorthiamid, chlorphthalim, Chlorflurenol-methyl, chlorpropham, chlorbromuron, chloroxuron, chlorotoluron, ketospiradox (ketospiradox) (including salts such as sodium, calcium or ammonium), Saflufenacil, sarmentine, cyanazine, cyanamide, diuron, acetochlor (d iethatyl-ethyl), dicamba (containing amine, diethylamine, isopropylamine, diglycolamine, sodium or lithium, etc.), cycloate, cycloxydim, dichlorosulfonate Diclosulam, cyclosulfamuron, cyclopyranil (common name, pyrazole herbicide), cyclopyrimorate (common name), dichlobenil, diclofop-P-methyl, he Diclofop-methyl, 2,4 drops of propionate (dichlorprop), 2,4 drops of propionate-P (dichlorprop-P), diquat (diquat), dithiopyr (dithiopyr), cyclic grass Siduron, dinitramine, cinidon-ethyl, cinosulfuron, dinoseb, dinoterb, cyanogen Cyhalofop-butyl, diphenamid, difenzoquat, diflufenican, diflufenzopyr, simazine, madochlor ( dimethachlor), dimethametryn, dimethenamid, dimethenamid-P, dimethenamid-P, simetryn, dimepiperate,

Dimefuron, cinmethylin, swip, sulcotrione, sulfentrazone, sulfosate, sulfosulfuron , Sulfometuron-methyl, sethoxydim, terbacil, daimuron, thaxtomin A (common name), dalapon, thiazopyr ), tiafenacil, thiencarbazone (including sodium salts, methyl esters, etc.), tiocarbazil, thiobencarb, thidiazimin, thiophene Thidiazuron, thifensulfuron-methyl, desmedipham, desmetryne, tetflupyrolimet (common name), thenylchlor, thenylchlor, tebutam, special Tebuthiuron, tepraloxydim, tefuryltrione, terbuthylazine, terbutryn, terbumeton, tembotrione , Topramezone (topramezone), oxachlor (tralkoxydim), three

Triaziflam, triasulfuron, triafamone, tri-allate, trietazine, triclopyr, triclosan (triclopyr-butotyl), tritosulfuron (tritosulfuron), trifludimoxazin (common name), triflusulfuron-methyl (triflusulfuron-methyl), trifluralin (trifluralin), trifloxysulfuron-sodium , Tribenuron-methyl, tolpyralate (tolpyralate), sodium naptalam (including sodium and other salts), naproanilide, napropamide, napropamide, napropamide-M, Nicosulfuron, neburon, norflurazon, vernolate, paraquat dichloride, halauxifen-benzyl, Haloxyifen-methyl, haloxyfop, haloxyfop-P, haloxyfop-etotyl, halosafen, Halosulfuron-methyl, bixlozone (bixlozone), picloram, picolinafen, bicyclopyrone, bispyribac-sodium, azole Pinoxaden, bifenox, piperophos, pyraclonil, pyrasulfotole, pyrazoxyfen, pyrazosulfuron -ethyl), pyrazolynate, pyranafos, pyraflufen-ethyl, pyridafol, pyrithiobac-sodium, pyridate ), pyriftalid, pyributicarb, pyribenzoxim , Pyrimsulfan (pyrimisulfan), pyriminobac-methyl, pyroxasulfone, pyroxasulfone, pyroxsulam, phenisopham, fenuron, fenoxasulfone ( common name),

Fenoxaprop (containing methyl, ethyl, isopropyl ester), refined

Fenoxaprop-P (containing methyl, ethyl, isopropyl ester), fenquinotrione (common name), fenthiaprop-ethyl, fenthiaprop-ethyl, fentrazamide, beetin (phenmedipham), butachlor, butafenacil, butamifos, butylate, butenachlor, butralin, butylene Butroxydim, flazasulfuron, flamprop (containing methyl, ethyl, isopropyl ester), flamprop-M (including methyl, ethyl, isopropyl Ester), primisulfuromethyl (primisulfuro-n-methyl), fluazifop-butyl, fluazifop-P-butyl, fluazifop-P-butyl, fluazolate, fluazolate, fluometuron ), fluoroglycofe orthoethyl, flucarbazone-sodium, fluchloralin, flucetosulfuron,

Fluthiacet-methyl, flupyrsulfuro-n-methyl (containing sodium, calcium, or ammonium salts), flufenacet, and flufenacet

Flufenpyr-ethyl, flupropanate, flupoxame, flumioxazin, flumiclorac-pentyl, flumetsulam , Fluridone, flurtamone, fluroxypyr (including butyl methyl ester, methyl heptyl ester and other esters, sodium, calcium or ammonium and other salts), flurochloridone (flurochloridone ), pretilachlor, procarbazone-sodium, prodiamine, prodiuron, prosulfuron, prosulfocarb, propaquizafop, Propachlor, propazine, propanil, propyzamide, propisochlor, propionate

Propyrisulfuron, Propham, Profluazol, Prohexadione-calcium, Propoxycarbazone, Propoxycarbazone-sodium, Ring Profoxydim, bromacil, brompyrazon, prometryn, prometon, bromoxynil (including butyric acid, caprylic acid or enanthic acid, etc.) (Ester), bromofenoxim, bromobutide, flosulam, florpyrauxifen, florpyrauxifen-benzyl, hexazinone ) Penthoxamid, benazolin, penoxsulam, heptamaloxyloglucan (heptamaloxyloglucan), beflubutamid, beflubutamid-M, butene Pebulate, pelargonic acid, bencarbazone, pendimethalin, benzfendizone, bensulide, bensulfuron-methyl ), benzobicyclon, benzofenap, bentazone, pentanochlor, pentoxazone, benfluralin, furfur yellow (benfuresate), fosamine, fomesafen, foramsulfuron, forchlorfenuron, 2-methyl-4 chloropropionic acid (mecoprop) (including (Sodium, potassium, isopropylamine, triethanolamine, dimethylamine and other salts), mecoprop-P-potassium, mesosulfuron (including methyl esters and other esters), nitrate Mesotrione, metazachlor,

Pyrazosulfuron (metazosulfuron), thiazolone (methabenzthiazuron), benzene

Metamitron,

Metamifop, metam, disodium methyl arsenate (DSMA), metiozolin (common name), methyldymuron, metoxuron, sulfoxazone (metoxuron) metosulam), metsulfuron-methyl, metobromuron, metobenzuron, metolachlor, metribuzin, mepiquat chloride, Mefenacet, monosulfuron (containing methyl, ethyl, and isopropyl esters), monolinuron, molinate, iodosulfuron, and formazan Iodosulfulon-methyl-sodium, iofensulfuron (iofensulfuron), iofensulfuron-sodium, iofensulfuron-sodium, lactofen, lancotrione (common name), and liyoulong (linuron), rimsulfuron, lenacil, 2,2,2-trichloroacetic acid (TCA) (including sodium, calcium or ammonium salts), 2,3,6-trichloro Benzoic acid (2,3,6-TBA), 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), 2,4-dichlorophenoxyacetic acid (2,4-D ) (Including amine, diethylamine, triethanolamine, isopropylamine, sodium or lithium and other salts), 2-amino-3-chloro-1,4-naphthoquinone (ACN), 2-methyl-4-chlorobenzene Oxyacetic acid (MCPA) (including sodium salt, ethyl ester, etc.), 2-methyl-4-chlorophenoxybutyric acid (MCPB) (including sodium salt, ethyl ester, etc.), 4-(2,4 -Dichlorophenoxy)butyric acid (2,4-DB), 4,6-dinitro-O-cresol (DNOC) (including salts such as amine or sodium), AE-F-150944 (coding serial number) , IR-6396 (coding serial number), MCPA-thioethyl (MCPA-thioethyl), SYP-298 (coding serial number), SYP-300 (coding serial number), S-ethyldipropylthiocarbamate ( EPTC), S-metolachlor, S-9750 (coding serial number), MSMA (MSMA), HW-02 (coding serial number), NC-653 (coding serial number), S-523 (coding serial number) , SL-1201 (coding serial number).

Plant Growth Regulator:

1-naphthylacetamide, 1-methylcyclopropene, 2,6-diisopropylnaphthalene, 4-oxo-4- (2-Phenylethyl)aminobutyric acid (chemical name, CAS registration number: 1083-55-2), 4-chlorophenoxyacetic acid (4-CPA), n-decanol (n-decanol), Ai Aviglycine, ancymidol, abscisic acid, inabenfide, indole acetic acid, indole butyric acid, monogram ( uniconazole), monoiconazole-P (uniconazole-P), Ecolyst (Ecolyst), indyl ester (ethychlozate), ethephon, eprophon, epocholeone, oxin sulfate ( oxine-sulfate, carvone, calcium formate, cloxyfonac, cloxyfonac-potassium, cloprop, chlormequat, choline (choline), cytokinins, cyclanilide, dikegulac, gibberellin acid, dimethipin, sintofen, dingyin Hydrazine (daminozide), thidiazuron, triacontanol, trinexapac-ethyl, paclobutrazol, paraffin, flumetralin, furimidine (flurprimidol), flurenol, pronitridine (generic name), propyl jasmonate (prohydrojasmon), prohexadione-calcium, heptamaloxyloglucan (generic name), benzylaminopurine (benzylaminopurine), chlorine Forchlorfenuron, maleic hydrazide, mepiquat chloride, mefluid ide), calcium peroxide.

Secondly, examples of well-known phytotoxicity-reducing compounds that can be mixed or used together are exemplified as under.

唑酸(isoxadifen)、雙苯

唑酸乙酯(isoxadifen-ethyl)、解草腈(oxabetrinil)、解毒喹(cloquintcet-mexyl)、增效磷(dietholate)、解草胺腈(cyometrinil)、二氯丙烯胺(dichlormid)、二環酮(dicyclonone)、環丙磺醯胺(cyprosulfamide)、1,8-萘二甲酸酐(1,8-Naphthalic Anhydride)、解草唑(fenchlorazole-O-ethyl)、解草啶(fenclorim)、解草

唑(furilazole)、氟草肟(fluxofenim)、解草胺(flurazole)、解草酮(benoxacor)、mephenate(通用名)、吡唑解草酸(mefenpyr)、吡唑解草酸乙酯(mefenpyr-ethyl)、吡唑解草酸二乙酯(mefenpyr-diethyl)、低級烷基取代苯甲酸、2,2-二氯-N-(1,3-二

烷-2-基甲基)-N-(2-丙烯基)乙醯胺(PPG-1292)、2-二氯甲基-2-甲基-1,3-二

烷(MG-191)、3-二氯乙醯基-2,2，5-三甲基-1,3-

唑烷(R-29148)、4-二氯乙醯基-1-氧雜-4-氮雜螺環[4.5]癸烷(AD-67)、MON4660(編碼序號)、metcamifen(通用名)、N1,N2-二烯丙基-N2-二氯乙醯基甘胺醯胺(DKA-24)、TI-35(編碼序號)。 Bisbenzene

Izodic acid (isoxadifen), bisbenzene

Isoxadifen-ethyl, oxabetrinil, cloquintcet-mexyl, dietholate, cyometrinil, dichlormid, dicyclo Dicyclonone, cyprosulfamide, 1,8-Naphthalic Anhydride, fenchlorazole-O-ethyl, fenclorim, fenclorim grass

Furilazole, fluxofenim, flurazole, benoxacor, mephenate (common name), mefenpyr, mefenpyr-ethyl ), mefenpyr-diethyl pyrazolate (mefenpyr-diethyl), lower alkyl substituted benzoic acid, 2,2-dichloro-N-(1,3-di

Alkan-2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292), 2-dichloromethyl-2-methyl-1,3-di

Alkane (MG-191), 3-dichloroacetyl-2,2,5-trimethyl-1,3-

Oxazolidine (R-29148), 4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (AD-67), MON4660 (coding number), metcamifen (common name), N1,N2-diallyl-N2-dichloroacetamideglycamine (DKA-24), TI-35 (coding number).

The pest control agent of the present invention constituted as described above is suitable for orthoptera pests, Thysanoptera pests, hemiptera pests, Coleoptera pests, Diptera pests, Lepidoptera pests, Hymenoptera pests, and Pteroceras pests. , Chlamydomonas pests, Blattidae pests, Rodentes pests, Trichoderma pests, Liceles pests, plant parasitic mites, plant parasitic nematodes, plant parasitic mollusks, other harmful animals, unpleasant Comfortable animals, sanitary pests, parasites and other harmful organisms show excellent control effect. Such pests can be exemplified by the following biological species.

Orthoptera pests include, for example: Ruspolia lineosa (Ceramidae) and others; Teleogryllus emma (Truljalia) and Cricket (Truljalia) hibinonis), etc.; Griflotalpa orientalis, Oxya hyla intricate, Locusta migratoria, Melanoplus sanguinipes, Melanoplus differentialis, red shank Black locust (Melanoplus femurrubrum), etc.; Atractomorpha lata carrying the locust family; Euscyrtus japonicus; Xya japonicus such as the flea locust family.

Examples of the Thysanoptera pests are: Thrips Taiwan thrips (Frankliniella intonsa), Western thrips (Frankliniella occidentalis), Small yellow thrips (Scirtothrips dorsalis), Southern yellow thrips (Thrips palmi), Onion thrips (Thrips palmi) Thrips tabaci), Japanese tobacco thrips (Thrips setosus), leaf thrips (Heliothrips haemorrhoidalis), rice thrips (Stenchaetothrips biformis), etc.; persimmon thrips (Ponticulothrips diospyrosi), mustard tube thrips (Liothrips wasabiae), rice tube thrips (Haplothrips aculeatus), etc.

梨椿象(Urochela luteovoria)等；長椿象科之甘蔗小翅長椿象(Cavelerius saccharivorus)等；突眼長椿象科之豆突眼長椿象(Malcus japonicus)等；紅椿象科之離斑棉紅椿象(Dysdercus cingulatus)等；蛛緣椿象科之禾蛛緣椿象(Leptocorisa acuta)、中華稻緣椿象(Leptocorisa chinensis)等；緣椿象科之紋鬚同緣椿象(Anacanthocoris striicornis)等；姬緣椿象科之赤姬緣椿象(Rhopalus maculatus)等；土椿象科之褐土椿象(Scaptocoris castanea)等；臭蟲科之溫帶臭蟲(Cimex lectularis)等。 Hemiptera pests include, for example: Mogannia minuta and the like; Aphrophora intermedia of Cercopidae, Acanophora intermedia, Mahanarva fimbriolata, etc.; Brown-horned cicada (Machaerotypus sibiricus), etc.; grape leaf cicada (Arboridia apicalis), tea small green leaf cicada (Empoasca onukii), pseudo black-tailed cicada (Nephotettix cincticeps), Malayan black-tailed cicada (Nephotettix malayanus) ), Taiwan black-tailed leafhopper (Nephotettix virescens), black-striped blacktail leafhopper (Nephotettix nigropictus), electro-optic leafhopper (Recilia dorsalis), two-pointed green leafhopper (Amrasca biguttula), lemon fruit brown leafhopper (Idioscopus nitidulus) , Idioscopus clypealis, Amritodus atkinsoni), potato leafhopper (Empoasca fabae), corn leafhopper (Dalbulus maidis), etc.; Pentastiridius apicalis, etc.; Laodelphax striatellus , Brown planthopper (Nilaparvata lugens), white-backed planthopper (Sogatella furcifera), corn planthopper (Peregrinus maidis), etc.; the brown planthopper (Nisia nervosa) of the onion plant family (Nisia nervosa), etc.; (Kamendaka saccharivora), etc.; Achilus flammeus, etc.; Ochianga japonicus, etc.; Grass brown brown moth wax of the blue-winged planthopper. Cicada (Mimophantia maritima), etc.; Cacopsylla pyrisuga, Diaphorina citri, etc.; Mango psyllium (Calophya mangiferae) of Ficus plutidae; Calophya mangiferae, etc.; Daktulosphaira vitifoliae), etc.; Adelges laricis, Adelges tsugae, etc.; Acyrthosiphon pisum, Aphis g. ossypii), Aphis spiraecola, Lipaphis erysimi, vegetable aphid (Brevicoryne brassicae), pink aphid (Myzus persicae), wheat green aphid (Schizaphis graminum), rice wheat aphid (Rhopalosiphum padi), Toxoptera aurantii, Aulacorthum solani, Macrosiphum euphorbiae, Nasonovia ribisnigri, Sitobion avenae, Aphis glycines Etc.; Aleurocanthus camelliae, Aleurocanthus spiniferus, Bemisia tabaci, Bemisia argentifolii, Greenhouse mealworm (Trialeurodes vaporariorum) Etc.; Drosicha corpulenta, Icerya purchasi, etc.; Dysmicoccus brevipes, Planococcus citri, mulberry Pseudococcus comstocki, etc.; Ceroplastes ceriferus, Ceroplastes rubens, etc.; Aclerda takahashii, etc.; Shield scale insects Aonidiella aurantii, Diaspidiotus perniciosus, Pseudaulacaspis pentagona, Unaspis yanonensis, etc.; American forage Lygus lineolaris, Trigonotylus caelestialium, Apolygus lucorum, Nesidiocoris tenuis, Halticus bractatus, etc.; Rhododendron armyworm (Stephanitis pyrioi des), Stephanitis nashi, etc.; Eurydema rugosum, Eysarcoris lewisi, Eysarcoris aeneus, Lagynotomus elongatus, southern green stink bug (Nezara) viridula), Plautia crossota, Nezara antennata, Euchistus heros, Piezodorus guildini, Tibraca limbativentris, Dichelops furcatus, etc. ; Taiwan round stink bug (Megacopta cribraria), etc.;

Pear stink bug (Urochela luteovoria), etc.; sugarcane small-winged stink bug (Cavelerius saccharivorus), etc.; pieropsis stink bug (Malcus japonicus), etc.; spotted cotton red stink bug of the red stink bug ( Dysdercus cingulatus); Leptocorisa acuta, Leptocorisa chinensis, etc.; Anacanthocoris striicornis etc. Rhopalus maculatus, etc.; Scaptocoris castanea, etc.; Cimex lectularis, etc.

Coleoptera pests include, for example: Anomara cuprea (Anomara cuprea), red copper beetle (Anomara rufocuprea), bean chafer (Popillia japonica), blue-and-white chafer (Oxycetonia jucunda), cherry chamomile (Anomala geniculata) ), coconut rhinoceros chafer (Oryctes rhinoceros), brown chafer (Heptophylla picea), June chafer (Phyllophaga cuyabana), etc.; Agriotes ogurae, Agriotes ogurae, Agriotes lineatus, Dark color beetle (Agriotes obscurus), Okinawa comb claw beetle (Melanotus okinawensis), round head comb claw beetle (Melanotus fortnumi), etc.; Anthrenus verbasci, etc.; two outbursts of the long beetle family Heterobostrychus hamatipennis, etc.; Stegobium paniceum, etc.; Pitinus clavipes, etc.; Tenebroides mauritanicus, etc.; Necrobia rufipes of the family Guogongidae; Carpophilus hemipterus and Meligethes seneus, etc.; A. versicolor flatworms (Ahasverus) advena); etc.; Cryptolestes ferrugineus, etc.; Epilachna varivestis, Henosepilachna vigintioctopunctata, etc.; Psedidae Tenebrio molitor, Tribolium castaneum, etc.; Epicauta gorhami, etc.; Anoplophora glabripennis, Xylotrechus pyrrhoderus, Monochamus alternatus, Soybean black beetle (Dectes texanus), etc.; Mung bean elephant of the legume family (Callosobruchus chinensis) Etc.; Colorado golden bug (Leptinotarsa decemlineata) and western corn rootworm (Diabrotica virgifera) virgifera), northern corn rootworm (Diabrotica barberi), southern corn rootworm (Diabrotica undecimpunctata howardi), yellow guard melon (Aulacophora femoralis), cabbage flower bug (Phaedon brassicae), beet beetle (Cassida nebulosa), rice negative mud Insects (Oulema oryzae), Mexican soybean ladybug (Epilachna varivestis), yellow leaf fleas (Phyllotreta striolata), tea Xiao leaf beetle (Demotina fasciculata), rapeseed golden beetle (Psylliodes chrysocephala), kidney bean yellow beetle (Cerotoma trifurcate) ), Colaspis brunnea, Colaspis crinnicornis, Odontota horni, Chaetocnema pulicaria, Diabrotica balteata, etc.; The sweet potato ant elephant (Cylas formicarius) of the weevil family; the alfalfa leaf weevil (Hypera postica), the vegetable weevil (Listroderes costirostris), the sweet potato weevil (Euscepes postfasciatus), the chestnut weevil ( Curculio sikkimensis), Mexican cotton boll weevil (Anthonomus grandis), bean stem weevil (Sternechus subsignatus), etc.; two-star rice elephant (Echinocnemus bipunctatus), rice root weevil (Lissorhoptrus oryzophilus), South America Rice weevil (Oryzophagus oryzae), etc.; corn weevil (Sitophilus zeamais), coccinus weevil (Sphenophorus venatus), sugarcane weevil (Sphenophorus levis), etc.; Longitudinal pit-cutting bark beetle (Tomicus piniperda), etc.; Long-tailed bark beetle family (Crossotarsus niponicus), etc.; Powdered beetle family (Lyctus brunneus), etc.

Diptera pests include, for example: Tipula aino, etc.; Plecia nearctica, etc.; Exechia shiitakevora, etc.; Black-winged fungus Potato black-winged fungus (Pnyxia scabiei), dwarf black-fed fungus (Bradysia agrestis), etc.; Soybean pod gallflies (Asphondylia) yushimai), wheat gallet (Mayetiola destructor), blueberry gallet (Dasineura oxycoccana), etc.; Aedes aegypti, Culex pipiens pallens, etc.; Simulium takahashii Chironomus oryzae, etc.; Chrysops suavis, Tabanus trigonus, etc.; Eumerus strigatus, Syrphidae, etc.; fruit fly family Eastern fruit fly (Bactrocera dorsalis), Japanese cherry fruit fly (Euphranta japonica), Mediterranean fruit fly (Ceratitis capitata), etc.; Liriomyza trifolii, Liriomyza trifolii sativae), Agromyza oryzae, Liriomyza bryoniae, Chromatomyia horticola, Liriomyza chinensis, Liriomyza trifolii, etc.; Meromyza nigriventris, etc.; Drosophila suzukii, Drosophila melanogaster, etc.; Hydrellia griseola, etc.; Hippobosca equina, etc.; Parallelpmma sasakawae, etc.; Delia antiqua, Delia platura, etc.; Toilet Fannia canicularis, etc.; Musca domestica, Stomoxys calcitrans, etc.; Sarcophaga peregrina, etc.; Gasterophilus intestinalis), etc.; Bovine fly (Hypoderma lineatum) of Bovidae (Hypoderma lineatum), etc.; Oestrus ovis (Oestrus ovis), etc.

For example, Lepidoptera pests include: Endoclita excrescens of the family Helicopteridae; Antispila ampelopsia, etc.; Six-star black spot moth (Zeuzera leuconotum) ), Colesus moth (Cossus insularis), etc.; Archips fuscocupreanus, Adoxophyes orana fasciata, Grapholitha molesta, Homona magnanima, Leguminivora glycinivorella), apple codling moth (Cydia pomonella), grape flower winged small moth (Lobesia botrana), etc.; grape leaf moth (Eupoecilia ambiguella), etc.; black moth (Bambalina) sp.), Eumeta minuscula, etc.; Nemapogon granella, Tinea translucens, etc.; Bucculatrix pyrivorella, etc.; leaf moth Peach leaf moth (Lyonetia clerkella), silver leaf moth (Lyonetia prunifoliella malinella), etc.; tea moth (Caloptilia theivora), gold moth (Phyllonorycter ringoniella), etc.; citrus in the leaf moth family Leaf moth (Phyllocnistis citrella), etc.; Acrolepiopsis sapporensis, etc.; Plutella xylostella; Plutella xylostella; Apple nest moth (Yponomeuta orientalis), etc.; Silver moth Apple silver moth (Argyresthia conjugella), etc.; Nokona regalis, Synanthedon hector, etc.; Potato wheat moth (Phthorimaea operculella), wheat moth (Sitotroga) cerealella), cotton red bell moth (Pectinophora gossypiella), tomato leaf tooth moth (Tuta absoluta), etc.; fruit moth moth family Peach borer moth (Carposina sasakii), etc.; moth family Moth family pear leaf spot moth (Illiberis pruni) Etc.; Monema flavescens, etc.; Ancylolomia japonica, Chilo suppressalis, Chilo suppressalis, Cnaphalocrocis medinalis, Asian corn moth (Ostrinia furnacalis), cabbage moth (Hellulla undalis), peach flax moth (Conogethes punctiferlis), melon silk moth (Diaphania indica), bluegrass borer (Parapediasia teterrella), European corn borer (Ostrinia nubilalis), etc.; sugarcane stem borer (Diatraea saccharalis), meal moth (Cadra cautella), wax borer ( Galleria mellonella), etc.; Nippoptilia vitis, etc.; Papilio xuthus, Papilio xuthus, etc.; Pieris rapae, Pieridae; etc. (Parnara guttata), etc.; Ascotis selenaria, etc.; Dendrolimus spectabilis, Malacosoma neustrium testaceum, etc. Agrius convolvuli), etc.; Arna pseudoconspersa, Orygia recens approximans, Lymantria dispar, etc.; American white moth (Hyphantria cunea), etc.; Agrotis ipsilon, Agrotis segetum, Autographa nigrisigna, Helicoverpa armigera, Corn moth (Helicoverpa zea), Heliothis virescens ), Spodoptera exigua, Spodoptera litura, Chrysodeix includens, Spodoptera frugiperda, Nephelodes minians, etc.

Examples of Hymenoptera include: Arge pagana and other three species: Apethymus kuri, Athalia rosae ruficornis, etc.; Chestnut gall in the family Meloididae Bees (Dryocosmus kuriphilus), etc.; Vespa simillima xanthoptera, etc.; Solenopsis invicta, Linepithema humile, etc.; Megachile nipponica )Wait.

Examples of Pterocephalid pests are the yellow star roundworm (Bourletiella hortensis) and so on.

Examples of the tassel-tailed pests include Lepisma saccharina and Ctenolepisma villosa.

Examples of pests in the order Blattella include: Periplaneta americana in the family Blattella; Blattella germanica in the family Blattella germanica; Odontotermes formosanus in the termite family; Incisitermes minor, Cryptotermes domesticus; Coptotermes formosanus, Reticulitermes speratus, etc.

Pests of the order Rodentia include, for example, Trogium pulsatorium of the family Rodentia; Liposcelis corrodens of the family Leptidae.

Examples of the pests of the order Lepidoptera include Labodura riparia and the like.

Examples of the insects of the order Trichophyta include: Menopon pallidum of the short-horned bird lice family; Damalia bovis of the family Lepidoptera.

Examples of lice-order pests include: Haematopinus suis, etc.; Pediculus humanus, etc.; Linognathus setosus, etc.; Pthirus pubis, etc.

Examples of tick insects include: Penthaleus major, etc.; Phytonemus pallidus, Polyphagotarsonemus latus, etc.; one of the family Acaridae Siteroptes sp., etc.; Brevipalpus lewisi, etc.; Tuckerella pavoniformis, etc.; Eotetranychus, Tetranychus boreus), Citrus spider mite (Panonychus citri), Apple spider mite (Panonychus ulmi), Tetranychus urticae, Tetranychus urticae, Tetranychus kanzawai, etc.; Trisetacus pini, etc.; Aculops pelekassi, Epitrimerus pyri, Phyllocoptruta oleivora, tomato acarops (Aculops) lycopersici), etc.; Diptacus crenatae, etc.; Aleuroglyphus ovatus, Tyrophagus putrescentiae, Rhizoglyphus robini ; Varroa jacobsoni, etc.; Dermanyssus gallinae, etc.; Ornithonyssus sylvialum, etc.; Ornithonyssus sylvialum, etc. (Boophilus microplus), Rhipicephalus sanguineus, Haemaphysalis longicornis, etc.; Sarcoptes scabiei, etc.

Examples of plant parasitic nematodes include: Longiporinae (Xiphinema index), etc.; Trichodidae (Prichrichodorus minor) of the genus Trichodidae (Paratrichodorus minor), etc.; Rhabditidae), a species of C. elegans, etc.; Tylenchidae, Aglenchus sp., etc.; Tylodoridae, Cephalenchus sp., etc.; grains Nothotylenchus acris and Ditylenchus destructor in the family Anguina; Rotyllenchulus reniformis and Helicotylenchus dihystera in the Neploididae family (Hoplolaimidae) ) Etc.; Paratylenchus curvitatus (Paratylenchus) etc.; Meloidogyneae (Meloidogyneae) southern rhizobia (Meloidogyne incognita), Meloidogyne hapla, Meloidogyne javanica, Meloidogyne chitwoodi, Meloidogyne fallax, etc.; potato gold of Heteroderidae Nematode (Globodera rostochiensis), potato cyst nematode (Globodera pallida), soybean cyst nematode (Heterodera glycines), beet cyst nematode (Heterodera Schachtii), etc.; dwarf nematode (Terotylenchus) (Tylenchorhynchus claytoni), etc. ; One of the smooth pad blade nematodes (Psilenchus sp.) of the Psilenchus genus (Psilenchus sp.), etc.; one of the ringworm nematodes (Criconemoides sp.) of the Chriconemella family, etc.; the ones of the Tylenchulidiae family (Tylenchulidiae) Citrus root nematode (Tylenchulus semipenetrans), etc.; Sphaeronema camelliae, etc.; Radopholus citrophilus, Radopholus similis of the Bratylenchidae family ), pseudo-root rot nematode (Nacobbus aberrans), northern root rot nematode (Pratylenchus penetrans), southern root rot nematode (Pratylenchus coffeae), corn root rot nematode (Pratylenchus zeae), pineapple root rot nematode (Pratylenchus brachyurus), etc.; small teeth Iotonchium ungulatum, Iotonchidae, etc.; Aphelenchus avenae, Aphelenchus, etc.; Aphelenchoides besseyi, Aphelenchoidae, Aphelenchoidae ), Aphelenchoides fragariae, etc.; Parasitaphelenchidae pine wood nematode (Bursaphelenchus xylophilus), etc.

Examples of plant-parasitic mollusks include: Pomacea canaliculata of the apple snail family; Leavicaulis alte of the sauropoda family; Leavicaulis alte, etc.; Achatina fulica of the African snail family; mucus slugs Branch of Double Slugs (Meghimatium bilineatum), etc.; Succinea lauta, etc.; Discidae, Disc pauper, etc.; Zonitoides yessoensis Etc.; Limax flavus, Lehmannia valentiana, Deroceras reticulatum, etc.; Paracariella harimensis, etc. (Acusta despecta sieboldiana), flat snail (Bradybaena similaris), etc.

Other harmful animals, uncomfortable animals, sanitary pests, domestic animal pests, parasites and other harmful organisms can be exemplified by: Procambarus clarkii, etc.; Isopoda's gynecology (Porcellionidae), Porcellio scaber, etc.; Armadillidium vulgare, etc.; Scutigeromorpha, Scutigeridae, and Stenigeridae. Scolopendra subspinipes and other centipedes pest orders; Polydesmoidea, Polydesmoidea, Paradoxosomatidae, elegant acid, Oxipus gracilis, Diplopoda, and other insects; Spider order, red spider Theridiidae hasseltii), etc.; Chiracanthium japonicum, and other Turkish black fat tail scorpions (Androctonus crassicauda), etc.; Ascaris lumbricoides, etc.; Insects (Syphacia sp.), etc.; filarias (Wuchereria bancrofti), etc.; flatworm endoparasites such as liver flukes (Distomum sp.), Weisi lung fluke (Paragonimus westermanii), Yokogawa lung Flukes (Metagonimus yokokawai), Schistosoma japonicum, Taenia solium, Taeniarhynchus saginatus, encapsulated Echinococcus sp., Diphyllobothrium latum, etc.

The pest control agent of the present invention is resistant to existing pest control agents, and the pests exemplified above also exhibit a control effect. In addition, the pest control agent of the present invention can also be used for plants that have acquired characteristics such as insect resistance, disease resistance, and herbicide resistance through genetic recombination and artificial mating.

The term "plants endowed with resistance by breeding methods or gene recombination technology" in the present invention means not only the resistance given by mating of classical varieties, but also the resistance given by genetic recombination technology, as well as New plant breeding techniques (NBTs) combined with molecular biology techniques in mating techniques confer resistance to plants. New breeding techniques (NBTs) are recorded in the book "Let's understand the new plant breeding techniques" (International Literature Corporation, Ozawa Liang, Jiang Mianhao works), the review article "Genome Editing Tools in Plants" (Genes 2017, 8,399, Tapan Kumar Mohanta, Tufail Bashir, Abeer Hashem, Elsayed Fathi Abd_Allah and Hanhong Bae) etc.

Next, the production method, preparation method, and use of the compound of the present invention will be described in detail in the following examples, but the present invention is not limited by these examples. In addition, the melting point of the physical property value of the compound of the present invention was measured using an MP-500V trace melting point measuring device manufactured by YANACO. The refractive index was measured using an ABBE refractometer manufactured by ATAGO. ^{The 1} H NMR spectrum was measured using JNM-LA400 (400 MHz), JNM-LA300 (300 MHz) or JNM-ECS300 (300 MHz) manufactured by JEOL Ltd., using tetramethylsilane (TMS) as an internal standard. The high resolution energy mass analysis spectrum (HRMS) was measured using a Q Exactive Focus Hybrid Quadrupole-Orbitrap LC-MS/MS System (ESI, positive mode) manufactured by Thermo Fisher Scientific.

In addition, examples of production of intermediates for producing compounds of the present invention are also described.

[Example]

[Example 1]

4-fluoro-2-methyl-5-[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]-N-(2,2,2 -Production of trifluoroethyl) benzamide (the compound number of the present invention: A-0022)

(1) Manufacture of ethyl 2-fluoro-5-iodo-4-methylbenzimidate hydrochloride

烷20mL的混合物吹進氯化氫，在室溫下攪拌4日。反應結束後，在減壓下濃縮。所得的殘渣以乙酸乙酯清洗，得到粗製的目標物4.40g(產率67%)。 Under ice cooling, p-2-fluoro-5-iodo-4-methylbenzonitrile 5.00g (19.2mmol), ethanol 1.32g (28.7mmol), 1,4-bis

A mixture of 20 mL of alkane was blown into hydrogen chloride, and stirred at room temperature for 4 days. After the reaction was completed, it was concentrated under reduced pressure. The obtained residue was washed with ethyl acetate to obtain 4.40 g of crude target substance (yield 67%).

¹ H-NMR data (400 MHz, DMSO-d ₆ /TMS δ (ppm)): 8.26 (1H, d), 7.55 (1H, d), 4.62 (2H, q), 2.45 (3H, s), 1.44 ( 3H,t)

(2) Manufacture of 2-fluoro-5-iodo-4-methylbenzimidimide hydrazide hydrochloride

Under ice cooling, to a mixture of 0.73 g (14.6 mmol) of hydrazine monohydrate and 15 mL of ethanol was added 5.00 g (14.6 mmol of ethyl 2-fluoro-5-iodo-4-methylbenzimidate hydrochloride ), stirred at room temperature for 5 hours. After the reaction, the solvent was distilled off under reduced pressure to obtain a crude target. Used directly in the next step without purification.

(3) 5-(2-fluoro-5-iodo-4-methylphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazole (Compound No. of the present invention: J- 0002) manufacturing

At 85° C., a mixture of the crude 2-fluoro-5-iodo-4-methylbenzimidimide hydrazide hydrochloride (14.6 mmol) and trifluoroacetic anhydride 20 mL obtained in (2) above was sealed in a tube Stir for 2 hours. After the reaction was completed, water was added and extracted with ethyl acetate. The resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was washed with n-hexane to obtain Crude target 4.69g (yield 87%).

¹ H-NMR data (400 MHz, CDCl ₃ /TMS δ (ppm)): 8.69 (1H, d), 7.17 (1H, d), 4.70 (1H, s), 2.50 (3H, s)

(4) 5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazole (inventive Compound number: J-0001)

Under ice cooling, in 5-(2-fluoro-5-iodo-4-methylphenyl)-3-(trifluoromethyl)-1H-1,2,4-triazole 2.50g (6.74mmol), To a mixture of 7 mL of N,N-dimethylformamide, 1.21 g (8.76 mmol) of potassium carbonate and 1.05 g (7.40 mmol) of methyl iodide were added, and the mixture was stirred overnight at room temperature. After the reaction was completed, water was added and extracted with ethyl acetate. The resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 10: 1) to obtain 0.79 g of the target product (yield 30%) and as a vice The product of 3-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-5-(trifluoromethyl)-1H-1,2,4-triazole 0.54g (product Rate 21%).

Target ¹ H-NMR data (400 MHz, CDCl ₃ /TMS δ (ppm)): 8.06 (1H, d), 7.16 (1H, d), 3.91 (3H, s), 2.51 (3H, s)

By-product ¹ H-NMR data (400 MHz, CDCl ₃ /TMS δ (ppm)): 8.46 (1H, d), 7.09 (1H, d), 4.12 (3H, s), 2.45 (3H, s)

(5) 4-fluoro-2-methyl-5-[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]benzonitrile (present invention Compound number: H-0001)

5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazole 0.79g (2.1mmol) A mixture of 0.31 g (2.6 mmol) of zinc (II) cyanide, 0.47 g (0.41 mmol) of tetrakis(triphenylphosphine) palladium, and 10 mL of N,N-dimethylformamide was stirred at 80° C. for 4 hours. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine Wash and dry with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1) to obtain 0.58 g of the target product (yield 100%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.96 (1H, d), 7.26 (1H, d), 3.94 (3H, s), 2.70 (3H, s)

(6) 4-fluoro-2-methyl-5-[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]benzoic acid (of the present invention) Compound number: G-0001)

烷10mL的混合物，添加60%硫酸水溶液10mL而加熱迴流5小時。反應結束後，添加水以乙酸乙酯萃取，所得的有機層以飽和食鹽水清洗，以無水硫酸鎂乾燥。將溶劑在減壓下餾去，所得的殘渣以正己烷清洗，得到粗製的目標物0.56g(產率91%)。 In 4-fluoro-2-methyl-5-[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]benzonitrile 0.58g (2.0mmol ), 1,4-two

A mixture of 10 mL of alkane was added with 10 mL of 60% sulfuric acid aqueous solution and heated to reflux for 5 hours. After the reaction was completed, water was added and extracted with ethyl acetate. The resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was washed with n-hexane to obtain 0.56 g of crude target product (yield 91%).

¹ H-NMR data (400 MHz, DMSO-d ₆ /TMS δ (ppm)): 13.24 (1H, s), 8.15 (1H, d), 7.51 (1H, d), 3.91 (3H, s), 2.64 ( 3H,s)

(7) 4-fluoro-2-methyl-5-[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]-N-(2, Production of 2,2-trifluoroethyl)benzamide (the compound number of the present invention: A-0022)

Under ice cooling, in 4-fluoro-2-methyl-5-[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]benzoic acid 0.44g (1.5mmol), 2,2,2-trifluoroethylamine 0.17g (1.7mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride 0.33g ( 1.7 mmol), 1-hydroxybenzotriazole monohydrate 0.20 g (1.3 mmol), and dichloromethane 2 mL, triethylamine 0.35 g (3.5 mmol) was added, and the mixture was stirred overnight at room temperature. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Reduce the solvent The residue was distilled off under reduced pressure, and the resulting residue was washed with n-hexane to obtain 0.47 g (yield 84%) of the crude target product.

¹ H-NMR data (400 MHz, CDCl ₃ /TMS δ (ppm)): 7.70 (1H, d), 7.16 (1H, d), 6.70 (1H, s), 4.08 (2H, sext), 3.92 (3H, d), 2.55(3H,s)

[Example 2]

4-cyano-2-methyl-5-[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]-N-(cyclopropyl) Production of benzamide (the compound number of the present invention: A-0077)

(1) 4-fluoro-2-methyl-5-[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]-N-(cyclopropyl Base) benzamide (the compound number of the present invention: A-0008)

4-fluoro-2-methyl-5-[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]benzoic acid 1.00g (3.30mmol) A few drops of 0.54 g (4.3 mmol) of oxalyl chloride, N,N-dimethylformamide, and a mixture of 3.3 mL of chloroform were stirred at room temperature for 2 hours, and then concentrated under reduced pressure. The resulting concentrate was added to a chloroform solution 3.3 mL of 0.23 g (4.0 mmol) of cyclopropylamine and 0.40 g (3.95 mmol) of triethylamine under ice cooling, and stirred at room temperature overnight. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was washed with n-hexane to obtain 0.99 g of the target substance (yield 88%).

¹ H-NMR data (400 MHz, CDCl ₃ /TMS δ (ppm)): 0.62 (2H, q), 0.88 (2H, q), 2.55 (3H, s), 2.73 (1H, m), 3.90 (3H, s), 6.13 (1H, s), 7.12 (1H, d), 7.59 (1H, d)

(2) 4-cyano-2-methyl-5-[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]-N-(ring Propyl) Benzoamide (Compound No. of the Invention: A-0077)

4-fluoro-2-methyl-5-[1-methyl-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]-N-(ring A mixture of 0.64 g (1.9 mmol) of propyl)benzamide, 0.36 g (7.4 mmol) of sodium cyanide and 2 mL of dimethyl sulfoxide was stirred at 130° C. for 5 hours. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 2) to obtain 0.33 g of the target product (yield 51%).

¹ H-NMR data (400 MHz, CDCl ₃ /TMS δ (ppm)): 7.70 (1H, s), 7.61 (1H, s), 6.18 (1H, s), 3.97 (3H, s), 2.90 (1H, m), 2.56 (3H, s), 0.91 (2H, q), 0.63 (2H, q)

[Example 3]

5-[3-(ethylthio)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methyl-N-(2,2,2 -Production of trifluoroethyl) benzamide (compound number of the present invention: B-0583)

(1) Manufacture of 2-fluoro 5-iodo-4-methylbenzoic acid

50.00g (324.4mmol) of 2-fluoro-4-methylbenzoic acid was dissolved in 350mL of concentrated sulfuric acid. Under ice cooling, 58.90g (261.8mmol) of N-iodosuccinimide was added, and the mixture was stirred for 30 minutes while maintaining the same temperature. After that, it was stirred at room temperature for 2 hours. After the reaction was completed, the reaction solution was poured into ice water, extracted with ethyl acetate, and the resulting organic layer was washed with sodium thiosulfate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude target. It is used directly in the next step without purification.

(2) Manufacture of 2-fluoro-5-iodo-N,4-dimethyl benzohydrazide

After suspending 100.0 g (357.1 mmol) of crude 2-fluoro-5-iodo-4-methylbenzoic acid in 600 mL of chloroform, and adding 0.3 mL (6.15 mmol) of N,N-dimethylformamide, it was cooled in ice Next, 67.90 g (535.0 mmol) of oxalyl chloride was slowly dropped at 0 to 5°C, and then stirred at room temperature for 1.5 hours. After the reaction mixture was concentrated under reduced pressure, it was dissolved in 200 mL of chloroform. The resulting crude 200 mL of the imitation solution was added dropwise to 500 mL of a chloroform solution of 41.10 g (892.1 mmol) of methyl hydrazine under ice cooling, and the mixture was stirred at room temperature for 17 hours. After the reaction was completed, water was added and extracted with chloroform. The resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 2: 1 to 1:1) to obtain 117.3 g of the target product (yield 100%) ).

¹ H-NMR data (300 MHz, DMSO-d ₆ /TMS δ (ppm)): 7.85 (0.35H, d), 7.68 (0.65H, d), 7.37 (0.35H, d), 7.21 (0.65H, d ), 3.10 (1.95H, s), 2.97 (1.05H, s), 2.39 (1.05H, s), 2.35 (1.95H, s)

(3) Production of 2-(2-fluoro-5-iodo-4-methylbenzyl)-2-methyldiamine-1-thioformamide

A mixture of 110.0 g (357.0 mmol) of 2-fluoro5-iodo-N,4-dimethylbenzoylhydrazine, 63.10 g (649.3 mmol) of potassium thiocyanate, and 170 mL of 2M hydrochloric acid was heated to reflux for 3 hours. After leaving to cool at room temperature, a saturated sodium bicarbonate aqueous solution was added to the reaction mixture to make it alkaline, and a solid was precipitated. The solid was filtered, washed with water, and dried to obtain 113.2 g of crude target product (yield 86%).

(4) 5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazole-3-thiol (the compound number of the present invention: J -0003) manufacturing

2-(2-fluoro-5-iodo-4-methylbenzyl)-2-methyldiamine-1-thioformamide 101.0g (275.1mmol), sodium hydroxide 22.00g (550.0 mmol) and 500 mL of water were heated to reflux for 4.5 hours. After leaving to cool at room temperature, a 10% citric acid aqueous solution was added to the reaction mixture to make the reaction mixture acidic, and a solid was precipitated. The solid was filtered, washed with water, and dried to obtain 61.0 g of crude target product (yield: 64%).

¹ H-NMR data (300 MHz, DMSO-d ₆ /TMS δ (ppm)): 8.17 (1H, d), 7.57 (1H, d), 3.65 (3H, d), 2.46 (3H, s)

(5) 5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-3-(methylthio)-1H-1,2,4-triazole (inventive Compound number: J-0012)

In 5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazole-3-thiol 25.0g (71.6mmol), Rongalite 10.1g (65.5 mmol), potassium carbonate 14.8 g (107 mmol), and a mixture of 150 mL of N,N-dimethylformamide added 12.2 g (86.0 mmol) of methyl iodide, and stirred at room temperature for 6.5 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting crude product was washed with a mixed solvent of n-hexane and ethyl acetate (n-hexane: ethyl acetate = 10: 1) to obtain 23.4 g of the target product (yield 90%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.03 (1H, d), 7.12 (1H, d), 3.79 (3H, s), 2.62 (3H, s), 2.49 (3H, s)

(6) 4-fluoro-2-methyl-5-[1-methyl-3-(methylthio)-1H-1,2,4-triazol-5-yl]benzonitrile (present invention Compound number: H-0002)

5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-3-(methylthio)-1H-1,2,4-triazole 23.4g (64.4mmol) A mixture of 17.3 g (193 mmol) of copper cyanide and 150 mL of 1,3-dimethyl-2-imidazolidinone was heated and stirred at 110° C. for 6.5 hours. After leaving to cool at room temperature, an ammonia aqueous solution was added to the reaction mixture and extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3:1), and the resulting solid was washed with hexane to obtain 14.0 g of the target substance ( Yield 83%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.91 (1H, d), 7.21 (1H, d), 3.80 (3H, d), 2.64 (3H, s), 2.62 (3H, s)

(7) 4-fluoro-2-methyl-5-[1-methyl-3-(methylthio)-1H-1,2,4-triazole- Production of 5-yl]benzoic acid (Compound No. of the present invention: G-0283)

4-Fluoro-2-methyl-5-[1-methyl-3-(methylthio)-1H-1,2,4-triazol-5-yl]benzonitrile 14.0g (53.4mmol ) And 300 mL of 50% sulfuric acid aqueous solution were heated to reflux for 27 hours. After cooling at room temperature, ethyl acetate and saturated aqueous sodium bicarbonate were added. After adding hydrochloric acid to the resulting aqueous layer to make it acidic, it was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 14.3 g of the target product (yield 95%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.44 (1H, d), 7.12 (1H, d), 3.83 (3H, d), 2.70 (3H, s), 2.65 (3H, s)

(8) 4-fluoro-2-methyl-5-[1-methyl-3-(methylthio)-1H-1,2,4-triazol-5-yl]benzoic acid methyl ester (this Invention compound number: F-0290)

In 4-fluoro-2-methyl-5-[1-methyl-3-(methylthio)-1H-1,2,4-triazol-5-yl]benzoic acid 14.3g (50.8mmol) A mixture of 12.6 g (91.2 mmol) of potassium carbonate and 200 mL of N,N-dimethylformamide was added iodomethane 10.8 g (76.1 mmol) and stirred at room temperature for 2 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained crude product was washed with n-hexane to obtain 14.3 g of the target product (yield 95%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.23 (1H, d), 7.12 (1H, d), 3.89 (3H, s), 3.80 (3H, d), 2.69 (3H, s), 2.63 (s, 3H)

(9) 4-fluoro-2-methyl-5-[1-methyl-3-(methylsulfinyl)-1H-1,2,4-triazol-5-yl]benzoic acid methyl ester (Compound No. of the present invention: F-0292)

In 4-fluoro-2-methyl-5-[1-methyl-3-(methylthio)-1H-1,2,4-triazol-5-yl]benzoic acid methyl ester 14.3g (48.4 mmol) of chloroform solution 200mL under ice cooling, slowly add between 0 to 5 ℃ Chloroperoxybenzoic acid 12.2 g (46.0 mmol, 65% as converted purity) was stirred under ice cooling for 1 hour. After the reaction was completed, chloroform and a saturated sodium thiosulfate aqueous solution were added, and the organic layer was washed with a saturated sodium bicarbonate aqueous solution, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 3) to obtain 13.4 g of the target product (yield 89%).

(10) 4-fluoro-2-methyl-5-(1-methyl-3-{[(2,2,2-trifluoroacetoxy)methyl]sulfur)-1H-1,2, Production of methyl 4-triazol-5-yl)benzoate (Compound No. of the present invention: F-0215)

13.4-g methyl 4-fluoro-2-methyl-5-[1-methyl-3-(methylsulfinyl)-1H-1,2,4-triazol-5-yl]benzoate To 200 mL of (43.0 mmol) chloroform solution, 45.2 g (215.2 mmol) of trifluoroacetic anhydride was added, and after stirring at room temperature for 2 hours, it was further heated and stirred at 50°C for 2 hours. After cooling at room temperature, the solvent was distilled off under reduced pressure to obtain a crude target. It is used directly in the next step without purification.

(11) 4-fluoro-5-(3-mercapto-1-methyl-1H-1,2,4-triazol-5-yl)-2-methylbenzoic acid methyl ester (the compound number of the present invention: F-0283)

The crude 4-fluoro-2-methyl-5-(1-methyl-3-{[(2,2,2-trifluoroethoxycarbonyl)methyl]sulfur]- A mixture of 1H-1,2,4-triazol-5-yl)benzoic acid methyl ester, potassium carbonate 17.8 g (129 mmol), and methanol 120 mL was stirred at room temperature for 2.5 hours. After the reaction was completed, ethyl acetate was added, and then a 10% citric acid aqueous solution was added to make the reaction mixture acidic, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 16.7 g of a crude target product (yield: 100%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.21 (1H, d), 7.17 (1H, d), 3.90 (3H, s), 3.85 (3H, d), 2.72 (3H, s)

(12) 5-[3-(ethylthio)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methylbenzoic acid methyl ester (this Invention compound number: F-0312)

0.80 g (2.8 mmol) of crude 4-fluoro-5-(3-mercapto-1-methyl-1H-1,2,4-triazol-5-yl)-2-methylbenzoic acid methyl ester, To a mixture of potassium carbonate 0.59 g (4.3 mmol), Rongalite 0.17 g (1.1 mmol) and N,N-dimethylformamide 14 mL, 0.53 g (3.4 mmol) of ethyl iodide was added, and the mixture was stirred at room temperature for 1 hour and a half. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1) to obtain 0.51 g of the target product (yield 58%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.23 (1H, d), 7.12 (1H, d), 3.89 (3H, s), 3.79 (3H, d), 3.16 (2H, q), 2.69(3H,s), 1.42(3H,t)

(13) 5-[3-(ethylthio)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methylbenzoic acid (inventive Compound number: G-0305)

Methyl 5-[3-(ethylthio)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methylbenzoate 1.40g (4.53 0.57 g (14 mmol) of lithium hydroxide monohydrate was added to a mixture of 4 mmol), 4 mL of tetrahydrofuran, 4 mL of methanol, and 4 mL of water, and the mixture was stirred at room temperature for 15 hours. After the reaction was completed, ethyl acetate was added. After adding a 10% citric acid aqueous solution to the resulting aqueous layer to make it acidic, it was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.27 g of the target product (yield 95%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.43 (1H, d), 7.12 (1H, d), 3.83 (3H, d), 3.18 (2H, q), 2.70 (3H, s),1.43(3H,t)

(14) 5-[3-(ethylthio)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methyl-N-(2, 2,2-trifluoroethyl)benzamide (Compound No. of the invention: B-0583) Manufacturing

In 5-[3-(ethylthio)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methylbenzoic acid 0.30g (1.0mmol) A mixture of several drops of N,N-dimethylformamide and 5 mL of chloroform. Under ice cooling, 0.19 g (1.5 mmol) of oxalyl chloride was added, and the mixture was stirred at the same temperature for 1 hour. After the resulting reaction mixture was concentrated under reduced pressure, the residue was dissolved in 5 mL of chloroform, and added dropwise to 0.25 g (2.5 mmol) of 2,2,2-trifluoroethylamine and 0.31 g (3.1 mmol of triethylamine) under ice cooling (3.1 mmol) and 5 mL of chloroform, and the reaction mixture was stirred at room temperature for 5 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained solid was washed with n-hexane to obtain 0.34 g of the target product (yield 89%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.67 (1H, d), 7.12 (1H, d), 6.46 (1H, t), 4.16-4.01 (2H, m), 3.79 ( 3H, d), 3.15 (2H, q), 2.54 (3H, s), 1.42 (3H, t)

[Example 4]

5-{3-[(cyanoethyl)sulfur]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro-2-methyl-N-(2, Production of 2,2-trifluoroethyl)benzamide (Compound No. of the present invention: B-0879)

(1) 4-fluoro-2-methyl-5-[1-methyl-3-(methylthio)-1H-1,2,4-triazol-5-yl]-N-(2, Production of 2,2-trifluoroethyl)benzamide (Compound No. of the present invention: B-0529)

4-fluoro-2-methyl-5-[1-methyl-3-(methylthio)-1H-1,2,4-triazol-5-yl]benzoic acid 3.80g (13.5mmol) A few drops of N,N-dimethylformamide and 50 mL of chloroform. Under ice cooling, 3.09 g (24.4 mmol) of oxalyl chloride was added, and the mixture was stirred for 1 hour while maintaining the same temperature. After the resulting reaction mixture was concentrated under reduced pressure, the residue was dissolved in 10 mL of chloroform, and under ice cooling, 2.68 g (27.1 mmol) of 2,2,2-trifluoroethylamine and 3.01 g (29.8 of triethylamine) were added dropwise mmol) and chloroform 30mL, the reaction mixture was stirred at room temperature for 30 minutes bell. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with 10% citric acid aqueous solution, saturated sodium bicarbonate aqueous solution, water, and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained solid was washed with n-hexane to obtain 4.56 g of the target product (yield 93%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.66 (1H, d), 7.12 (1H, d), 6.46 (1H, t), 4.16-4.01 (2H, m), 3.79 ( 3H, d), 2.62 (3H, s), 2.53 (3H, s)

(2) 4-fluoro-2-methyl-5-[1-methyl-3-(methylsulfinyl)-1H-1,2,4-triazol-5-yl]-N-( Production of 2,2,2-trifluoroethyl)benzamide (Compound No. of the present invention: B-0530)

In 4-fluoro-2-methyl-5-[1-methyl-3-(methylthio)-1H-1,2,4-triazol-5-yl]-N-(2,2, 2-trifluoroethyl)benzamide 4.56g (12.6mmol) in 60mL of chloroform solution Under ice cooling, slowly add 3.01g (11.3mmol of m-chloroperoxybenzoic acid at 0 to 5°C, converted to 65% purity ), stirring under ice cooling for 4 hours. After the reaction was completed, chloroform and a saturated sodium thiosulfate aqueous solution were added, and the organic layer was washed with a saturated sodium bicarbonate aqueous solution, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1:1 to 1:3) to obtain 5.10 g of the target product (yield 100%) ).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.73 (1H, d), 7.15 (1H, d), 6.94 (1H, t), 4.14-4.04 (2H, m), 3.90 ( 3H, d), 3.02 (3H, s), 2.56 (3H, s)

(3) 2,2,2-trifluoroacetic acid [(5-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)aminecarboxamide]phenyl)- Production of 1-methyl-1H-1,2,4-triazol-3-yl)thio]methyl ester (Compound No. of the present invention: B-0377)

In 4-fluoro-2-methyl-5-(1-methyl-3-(methylsulfinyl)-1H-1,2,4-triazol-5-yl)-N-(2, 2,2-trifluoroethyl)benzamide 4.76g (12.6mmol) in chloroform solution 60mL added three 13.2 g (62.9 mmol) of fluoroacetic anhydride was heated and stirred at 50°C for 4 hours. After cooling at room temperature, the solvent was distilled off under reduced pressure to obtain a crude target. It is used directly in the next step without purification.

(4) 4-fluoro-5-(3-mercapto-1-methyl-1H-1,2,4-triazol-5-yl)-2-methyl-N-(2,2,2-tri Production of fluoroethyl) benzamide (compound number of the present invention: B-0504)

The crude 2,2,2-trifluoroacetic acid [(5-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)aminecarboxamide]phenyl}- A mixture of 1-methyl-1H-1,2,4-triazol-3-yl)thio]methyl ester, potassium carbonate 5.22 g (37.8 mmol), and methanol 60 mL was stirred at room temperature for 2 hours. After the reaction was completed, ethyl acetate was added, and then a 10% citric acid aqueous solution was added to make the reaction mixture acidic, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 3.82 g of crude target product (yield 87%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.63 (1H, d), 7.14 (1H, d), 6.54 (1H, t), 4.16-4.04 (2H, m), 3.81 ( 3H, d), 2.54 (3H, s)

(5) 5-{3-[(2-cyanoethyl)sulfur]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro-2-methyl- Production of N-(2,2,2-trifluoroethyl)benzamide (Compound No. of the present invention: B-0879)

In crude 4-fluoro-5-(3-mercapto-1-methyl-1H-1,2,4-triazol-5-yl)-2-methyl-N-(2,2,2-tri Fluoroethyl) benzamide 1.00g (2.87mmol), potassium carbonate 0.60g (4.34mmol), Rongalite 0.41g (2.66mmol), N,N- dimethylformamide 26mL mixture was added 3-bromopropane Nitrile 0.46 g (3.43 mmol) was stirred at room temperature for 2 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1:1) to obtain 0.93 g of the target product (yield 81%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.68 (1H, d), 7.15 (1H, d), 6.36 (1H, t), 4.17-4.03 (2H, m), 3.81 ( 3H, d), 3.37 (2H, t), 2.94 (2H, t), 2.55 (3H, s)

[Example 5]

5-[3-(ethylsulfinyl)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methyl-N-(2,2 ,2-trifluoroethyl)benzamide (Compound No. of the present invention: B-0584)

In 5-[3-(ethylthio)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methyl-N-(2,2, 2-trifluoroethyl) benzamide 0.20g (0.53mmol) in chloroform solution 5mL under ice cooling, slowly add m-chloroperoxybenzoic acid 0.12g (0.45mmol, converted to 65% purity) at 0 to 5 ℃ ), stirring for 1 hour under ice cooling. After the reaction was completed, a saturated sodium thiosulfate aqueous solution was added, extracted with chloroform, and the organic layer was washed with a saturated sodium bicarbonate aqueous solution, water, and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 3) to obtain 0.15 g of the target product (yield 72%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.74 (1H, d), 7.16 (1H, d), 6.46 (1H, t), 4.17-4.03 (2H, m), 3.92 ( 3H, d), 3.30-3.19 (2H, m), 2.56 (3H, s), 1.35 (3H, t)

[Example 6]

5-[3-(Ethylsulfonyl)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methyl-N-(2,2, 2-Trifluoroethyl) Benzoamide (Compound No. of the Invention: B-0585)

In 5-[3-(ethylthio)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methyl-N-(2,2, 2-trifluoroethyl)benzamide 0.23g (0.61mmol) in chloroform solution 5mL added m-chloroperoxybenzoic acid 0.32g (1.2mmol, converted to purity 65%), stirred at room temperature for 15 minutes After 2 minutes, 0.32 g (1.2 mmol, converted to 65% purity) of m-chloroperoxybenzoic acid was added, and the mixture was stirred at room temperature for 14 hours. After the reaction was completed, a saturated sodium thiosulfate aqueous solution was added, extracted with chloroform, and the organic layer was washed with a saturated sodium bicarbonate aqueous solution, water, and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1: 3) to obtain 0.21 g of the target product (yield 84%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.75 (1H, d), 7.18 (1H, d), 6.32 (1H, t), 4.18-4.03 (2H, m), 3.97 ( 3H, d), 3.42 (2H, q), 2.57 (3H, s), 1.44 (3H, t)

[Example 7]

4-fluoro-2-methyl-5-{1-methyl-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2,4-triazol-5-yl} -Production of -N-(2,2,2-trifluoroethyl)benzamide (the compound number of the present invention: B-0027)

(1) Production of 5-(2-fluoro-5-iodo-4-methylphenyl)-1H-1,2,4-triazole-3-thiol (the compound number of the present invention: J-0005)

A mixture of 3.48 g (12.4 mmol) of 2-fluoro-5-iodo-4-methylbenzoic acid, 1.89 g (14.9 mmol) of oxalyl chloride, N,N-dimethylformamide and 13 mL of chloroform Stir at 50°C for 2 hours and concentrate under reduced pressure. The obtained concentrate was added to 13 mL of a pyridine solution of 1.13 g (12.4 mmol) of thiosemicarbazide under ice cooling, and stirred at room temperature overnight. After the reaction was completed, the resulting reaction mixture was concentrated under reduced pressure, 13 mL of a saturated sodium bicarbonate aqueous solution was added, and 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 of crude target product (yield 85%).

¹ H-NMR data (400 MHz, DMSO-d ₆ /TMS δ (ppm)): 13.8 (1H, s), 13.7 (1H, s), 8.24 (1H, d), 7.45 (1H, d), 2.41 ( 3H,s)

(2) 5-(2-fluoro-5-iodo-4-methylphenyl)-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2,4-triazole (Compound No. of the present invention: J-0018)

Under ice cooling, 5-(2-fluoro-5-iodo-4-methylphenyl)-1H-1,2,4-triazole-3-thiol 3.03g (9.04mmol), potassium carbonate 1.37g (9.91mmol), Rongalite 0.98g (6.36mmol), N,N-dimethylformamide 9mL mixture, add 2,20,2-trifluoroethyl trifluoromethanesulfonate 2,20g (9.48mmol) , Stir at room temperature for 3 hours. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4:1) to obtain 1.37 g of the target product (yield 36%).

¹ H-NMR data (400 MHz, CDCl ₃ /TMS δ (ppm)): 11.16 (1H, s), 8.63 (1H, d), 7.13 (1H, d), 3.91 (2H, q), 2.49 (3H, s)

(3) 5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2 , 4-Triazole (Compound No. of the Invention: J-0019)

In 5-(2-fluoro-5-iodo-4-methylphenyl)-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2,4-triazole 1.37g (3.28 mmol), a mixture of 0.50 g (3.62 mmol) of potassium carbonate and 3.5 mL of N,N-dimethylformamide, under ice cooling, 0.51 g (3.59 mmol) of methyl iodide was added, and the mixture was stirred overnight at room temperature. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 8: 1) to obtain the target substance 0.61g (yield 43.1%) and used as an auxiliary The product gives 3-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-5-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2 , 4-triazole 0.69g (yield 49%).

Target ¹ H-NMR data (400 MHz, CDCl ₃ /TMS δ (ppm)): 8.01 (1H, d), 7.13 (1H, d), 3.86 (2H, q), 3.79 (3H, s), 2.50 ( 3H,s)

By-product ¹ H-NMR data (400 MHz, CDCl ₃ /TMS δ (ppm)): 8.44 (1H, d), 7.08 (1H, d), 3.95 (2H, q), 3.91 (3H, s), 2.45 (3H,s)

(4) 4-fluoro-2-methyl-5-{1-methyl-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2,4-triazole-5 -Base} Benzonitrile (Compound No. of the present invention: H-0008)

5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2,4 -A mixture of 28.4 g (65.9 mmol) of triazole, 20.6 g (230 mmol) of copper (I) cyanide, and 100 mL of 1,3-dimethyl-2-imidazolidinone, and stirred at 100° C. for 7 hours. After the reaction was completed, water and ethyl acetate were added, and the mixture was filtered through celite. The obtained filtrate was extracted with ethyl acetate, washed with ammonia water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 19.9 g of crude target product (yield 92%).

¹ H-NMR data (400 MHz, CDCl ₃ /TMS δ (ppm)): 7.90 (1H, d), 7.23 (1H, d), 3.85 (2H, sext), 3.81 (3H, d), 2.65 (3H, s)

(5) 4-fluoro-2-methyl-5-{1-methyl-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2,4-triazole-5 -Group} benzoic acid (the compound number of the present invention: G-0153)

烷20mL的混合物，添加60%硫酸水溶液120mL而加熱迴流3.5小時。反應結束後，將所得的反應混合物注入於冰水，使固體析出。將固體過濾、水洗、乾燥，得到粗製的目標物19.8g(產率94%)。 In 4-fluoro-2-methyl-5-{1-methyl-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2,4-triazol-5-yl } Benzonitrile 19.9g (60.3mmol), 1,4-di

A mixture of 20 mL of alkane, 120 mL of a 60% sulfuric acid aqueous solution was added, and the mixture was heated to reflux for 3.5 hours. After the reaction was completed, the resulting reaction mixture was poured into ice water to precipitate a solid. The solid was filtered, washed with water, and dried to obtain 19.8 g of crude target product (yield 94%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.36 (1H, d), 7.15 (1H, d), 3.95-3.80 (5H, m), 2.73 (3H, s)

(6) Manufacture of 2-fluoro-N,4-dimethyl benzohydrazide

After suspending 60.00 g (389.3 mmol) of 2-fluoro-4-methylbenzoic acid in 500 mL of chloroform and adding 0.5 mL of N,N-dimethylformamide, the grass was slowly dropped at 0 to 5°C under ice cooling 88.90 g (700.4 mmol) of acetyl chloride was stirred at room temperature for 3 hours. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in 100 mL of chloroform. Under ice cooling, 500 mL of a chloroform solution of 71.7 g (1.56 mol) of methyl benzamine was dropped at 0 to 5°C, and stirred at room temperature for 22 hour. After the reaction was completed, water was added, extracted with chloroform, and the resulting organic layer was washed with saturated aqueous sodium bicarbonate solution, water, and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude target. It is used directly in the next step without purification.

¹ H-NMR data (300MHz, CDCl ₃ /TMS δ (ppm)): 7.38-7.26 (1H, m), 7.01 (1H, d), 6.95-6.88 (1H, m), 4.66 (1.4H, d) , 3.98 (0.6H, s), 3.35 (0.9H, s), 3.13 (2.1H, s), 2.38 (3H, s)

(7) Production of 2-(2-fluoro-4-methylbenzyl)-2-methyldiamine-1-thioformamide

A mixture of crude 2-fluoro-N,4-dimethylbenzoylhydrazine obtained in the above (6), 75.7 g (779 mmol) of potassium thiocyanate, and 400 mL of 2M hydrochloric acid was heated to reflux for 5 hours. After leaving to cool at room temperature, a saturated sodium bicarbonate aqueous solution was added to the reaction mixture to make it alkaline, and a solid was precipitated. The solid was filtered, washed with water, washed with n-hexane, and dried to obtain 94.3 g of a crude target product (yield: 100%).

¹ H-NMR data (300MHz, CDCl ₃ /TMS δ (ppm)): 7.38-7.26 (1H, m), 7.01 (1H, d), 6.95-6.88 (1H, m), 4.66 (1.4H, d) , 3.98 (0.6H, s), 3.35 (0.9H, s), 3.13 (2.1H, s), 2.38 (3H, s)

(8) 5-(2-fluoro-4-methylphenyl)-1-methyl-1H-1,2,4-triazole-3-thiol (the compound number of the present invention: J-0036) manufacture

2-(2-fluoro-5-iodo-4-methylbenzyl)-2-methyldiamine-1-thioformamide 94.30g (390.8mmol), sodium hydroxide 31.30g (782.6 mmol) and 500 mL of water were heated to reflux for 5 hours. After leaving to cool at room temperature, 1M hydrochloric acid was added to the reaction mixture to make the reaction mixture acidic, and a solid was precipitated. The solid was filtered, washed with water, washed with n-hexane, and dried to obtain 68.9 g of crude target product (yield 79%).

¹ H-NMR data (300 MHz, DMSO-d ₆ /TMS δ (ppm)): 7.60 (1H, t), 7.36 (1H, d), 7.26 (1H, d), 3.64 (3H, d), 2.41 ( 3H,s)

(9) 5-(2-fluoro-4-methylphenyl)-1-methyl-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2,4-tri Production of azole (Compound No. of the present invention: J-0035)

In 5-(2-fluoro-4-methylphenyl)-1-methyl-1H-1,2,4-triazole-3-thiol 30.00g (134.4mmol), Rongalite 15.90g (103.2mmol) , Potassium carbonate 33.40g (241.7mmol), N,N-dimethylformamide 350mL mixture was added trifluoromethanesulfonic acid 2,2,2-trifluoroethyl 37.4g (161.1mmol), at room temperature Stir for 2 hours.

After the reaction was completed, ethyl acetate was added, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 8: 1 to 3: 1) to obtain 32.5 g of the target product (yield 79%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.46 (1H, t), 7.11 (1H, dd), 7.04 (1H, d), 3.93-3.79 (5H, m), 2.44 ( 3H,s)

(10) 5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2 , 4-Triazole (Compound No. of the Invention: J-0019)

5-(2-fluoro-4-methylphenyl)-1-methyl-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2,4-triazole 20.0 g (65.5mmol) was dissolved in concentrated sulfuric acid 400mL, under ice cooling, add N-iodine amber Acetimide 15.5 g (68.9 mmol) was stirred at room temperature for 3 hours. After the reaction was completed, the reaction solution was poured into ice water, extracted with ethyl acetate, and the resulting organic layer was washed with sodium thiosulfate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5: 1) to obtain 28.3 g of the target product (yield 100%).

¹ H-NMR data (300MHz, CDCl ₃ /TMS δ (ppm)): 8.01 (1H, d), 7.13 (1H, d), 3.92-3.76 (5H, m), 2.50 (3H, s)

(11) 4-fluoro-2-methyl-5-{1-methyl-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2,4-triazole-5 -Methyl}benzoic acid methyl ester (Compound No. of the present invention: F-0160)

5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2,4 -Triazole 0.32g (0.74mmol), dichloride [1,1'-bis(diphenylphosphino)ironxin] palladium (II) dichloromethane adduct 11.4mg (0.014mmol), triethylamine A mixture of 0.14 g (1.38 mmol) and 1.5 mL of methanol was heated and stirred at 100° C. for 24 hours under a carbon monoxide environment (9.0 kg/cm ² ). After cooling at room temperature, ethyl acetate was added to remove insoluble materials by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3:1) to obtain 0.25 g of the target product (yield 93%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.21 (1H, d), 7.13 (1H, d), 3.95-3.75 (8H, m), 2.70 (3H, s)

(12) 4-fluoro-2-methyl-5-{1-methyl-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2,4-triazole-5 -Group} benzoic acid (the compound number of the present invention: G-0153)

In 4-fluoro-2-methyl-5-{1-methyl-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2,4-triazol-5-yl }Methyl benzoate 2.15g (5.92mmol), tetrahydrofuran 10mL, ethanol 10mL, water 10mL mixture was added lithium hydroxide monohydrate 0.74g (18mmol), stirred at room temperature 2 hour. After the reaction was completed, ethyl acetate and water were added, and a 10% citric acid aqueous solution was added to the resulting aqueous layer to make it acidic, followed by extraction with ethyl acetate, and the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 2.12 g of the target product (yield: 100%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.36 (1H, d), 7.15 (1H, d), 3.95-3.80 (5H, m), 2.73 (3H, s)

(13) 4-fluoro-2-methyl-5-{1-methyl-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2,4-triazole-5 -Yl}-N-(2,2,2-trifluoroethyl)benzamide (the compound number of the present invention: B-0027)

Under ice cooling, in 4-fluoro-2-methyl-5-{1-methyl-3-[(2,2,2-trifluoroethyl)sulfur]-1H-1,2,4-triazole 5-ethyl}benzoic acid 0.42g (1.2mmol), 2,2,2-trifluoroethylamine 0.14g (1.4mmol), dichloromethane 5mL mixture, 1-ethyl-3-(3- 0.28 g (1.5 mmol) of dimethylaminopropyl)carbodiimide hydrochloride was stirred at room temperature for 2 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1:1) to obtain 0.37 g of the target product (yield 72%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.67 (1H, d), 7.14 (1H, d), 6.42 (1H, t), 4.16-4.03 (2H, m), 3.90- 3.76(5H,m),2.55(3H,s)

[Example 8]

4-fluoro-2-methyl-5-{1-methyl-3-[(2,2,2-trifluoroethyl)thio]]-1H-1,2,4-triazole-5- Radical}-N-(2,2,2-trifluoroethyl)thiobenzamide (Compound No. of the present invention: B-0489)

4-fluoro-2-methyl-5-{1-methyl-3-[(2,2,2-trifluoroethyl)thio]]-1H- 1,2,4-triazol-5-yl)-N-(2,2,2-trifluoroethyl)benzamide 0.28g (0.65mmol), Lawson reagent 0.18g (0.45mmol), toluene The 4 mL mixture was heated to reflux for 3 hours. After cooling at room temperature, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3:1 to 1:1), and The obtained solid was washed with a mixed solvent of n-hexane and diisopropyl ether (n-hexane: diisopropyl ether = 1:1) to obtain 0.25 g of the target product (yield 86%).

¹ H-NMR data (300 MHz, DMSO-d ₆ /TMS δ (ppm)): 11.0 (1H, t), 7.47-7.37 (2H, m), 4.77-4.61 (2H, m), 4.13 (2H, q ), 3.77(3H,d), 2.33(3H,s)

[Example 9]

5-[3-(cyclopropylmethoxy)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methyl-N-(2,2 , 2-Trifluoroethyl) Benzoamide (Compound No. of the Invention: C-0029)

(1) Production of 2-(2-fluoro-5-iodo-4-methylbenzyl)-2-methyldiamine-1-carboxamide

A mixture of 2-fluoro5-iodo-N,4-dimethylbenzoylhydrazine 6.50 g (21.1 mmol), sodium cyanate 1.78 g (27.4 mmol), acetic acid 25 mL, and water 25 mL was heated to reflux for 2.5 hours. After leaving to cool at room temperature, the precipitated white solid was filtered, washed with n-hexane and dried to obtain 4.45 g of the target substance (yield 60%).

¹ H-NMR data (300 MHz, DMSO-d ₆ /TMS δ (ppm)): 8.43 (1H, s), 7.72 (1H, d), 7.25 (1H, d), 6.08 (2H, s), 3.07 ( 3H,s), 2.35(3H,s)

(2) 5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazol-3-ol (Compound No. of the present invention: J- 0031) Manufacturing

Combine 2-(2-fluoro-5-iodo-4-methylbenzyl)-2-methyldiamine-1-carboxamide 4.45g (12.7mmol) and sodium hydroxide 0.51g (12.8mmol) , 10mL water mixture is heated to reflux 1 hour. After leaving to cool at room temperature, a 10% citric acid aqueous solution was added to the reaction mixture to make the reaction mixture acidic, and a solid was precipitated. The solid was filtered, washed with water, washed with hexane, and dried to obtain 3.92 g of the target product (yield 93%).

¹ H-NMR data (300 MHz, DMSO-d ₆ /TMS δ (ppm)): 11.1 (1H, s), 7.97 (1H, d), 7.46 (1H, d), 3.56 (3H, d), 2.43 ( 3H,s)

(3) 3-(cyclopropylmethoxy)-5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazole (this Invention compound number: J-0034)

5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazol-3-ol 1.20g (3.60mmol), potassium carbonate 0.90g (6.5mmol), a mixture of 20mL of N,N-dimethylformamide was heated at 80°C for 5 minutes, 0.58g (4.3mmol) of 1-(bromomethyl)cyclopropane was added, and the mixture was heated and stirred at the same temperature 2 hour. After cooling at room temperature, ethyl acetate was added, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3: 1 to 1:1) to obtain 1.36 g of the target product (yield 98%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.02 (1H, d), 7.10 (1H, d), 4.11 (2H, d), 3.69 (3H, d), 2.48 (3H, s),1.40-1.25(1H,m),0.65-0.57(2H,m),0.41-0.34(2H,m)

(4) 5-[3-(Cyclopropylmethoxy)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methylbenzoic acid methyl ester (Compound No. of the present invention: F-0593)

3-(Cyclopropylmethoxy)-5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazole 1.28g (3.31 mmol), dichlorinated [1,1'-bis(diphenylphosphino)ironxin] palladium (II) dichloromethane adduct 54mg (0.066mmol), triethylamine 0.67g (6.6mmol), methanol The 3 mL mixture was heated and stirred at 100° C. for 5 hours under a carbon monoxide environment (9.0 kg/cm ² ). After cooling at room temperature, ethyl acetate was added to remove insoluble materials by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 8:1 to 3:1) to obtain 0.75 g of the target product (yield 71%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.23 (1H, d), 7.10 (1H, d), 4.12 (2H, d), 3.89 (3H, s), 3.70 (3H, d), 2.68 (3H, s), 1.40-1.25 (1H, m), 0.66-0.57 (2H, m), 0.41-0.34 (2H, m)

(5) 5-[3-(cyclopropylmethoxy)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methylbenzoic acid (this Invention compound number: G-0586)

0.73-g methyl 5-[3-(cyclopropylmethoxy)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methylbenzoate To a mixture of (2.3 mmol), 4 mL of tetrahydrofuran, 4 mL of methanol, and 4 mL of water, 0.29 g (6.9 mmol) of lithium hydroxide monohydrate was added, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, ethyl acetate and water were added. After adding a 10% citric acid aqueous solution to the resulting aqueous layer to make it acidic, it was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.68 g of the target product (yield 97%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.38 (1H, d), 7.10 (1H, d), 4.14 (2H, d), 3.73 (3H, d), 2.69 (3H, s),1.40-1.30(1H,m),0.65-0.57(2H,m),0.43-0.35(2H,m)

(6) 5-[3-(cyclopropylmethoxy)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methyl-N-( Production of 2,2,2-trifluoroethyl)benzamide (Compound No. of the present invention: C-0029)

In 5-[3-(cyclopropylmethoxy)-1-methyl-1H-1,2,4-triazol-5-yl]-4-fluoro-2-methylbenzoic acid 0.21g (0.69 mmol), a few drops of N,N-dimethylformamide, and 5 mL of chloroform. Under ice cooling, add 0.16 g (1.3 mmol) of oxalyl chloride and stir while maintaining the same temperature. 1 hour. After the resulting reaction mixture was concentrated under reduced pressure, the residue was dissolved in 5 mL of chloroform, and dropwise added to 2,2,2-trifluoroethylamine 0.14 g (1.4 mmol) and triethylamine 0.17 g (1.7 mmol) and 5 mL of chloroform, and the reaction mixture was stirred at room temperature for 2 hours. After the reaction was completed, ethyl acetate was added, and the organic layer was washed with 10% citric acid aqueous solution, saturated sodium bicarbonate aqueous solution, water, and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting solid was washed with n-hexane to obtain 0.21 g of the target product (yield 79%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.63 (1H, d), 7.08 (1H, d), 6.80 (1H, t), 4.17-4.03 (4H, m), 3.69 ( 2H, d), 2.53 (3H, d), 2.69 (3H, s), 1.39-1.28 (1H, m), 0.67-0.58 (2H, m), 0.42-0.34 (2H, m)

[Example 10]

N-ethyl-4-fluoro-2-methyl-5-{1-methyl-3-[(2,2,2-trifluoroethyl)thio]]-1H-1,2,4- Production of triazol-5-yl}benzamide (compound number of the present invention: B-0003)

烷4.0mL的混合物在一氧化碳環境下(9.0kg/cm²)、在110℃下加熱攪拌8小時。在室溫下放冷後，添加乙酸乙酯，將不溶物以過濾除去，將溶劑在減壓下餾去。將殘渣以氧化矽凝膠管柱層析法(展開溶劑，正己烷：乙酸乙酯=5：1至2：1)精製，得到目標物0.21g(產率69%)。 5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-3-[(2,2,2-trifluoroethyl)thio]]-1H-1,2 ,4-triazole 0.35g (0.81mmol), [1,1'-bis(diphenylphosphino)ironxin]palladium (II) dichloromethane adduct 13.3mg (0.016mmol), ethyl Amine hydrochloride 0.16g (2.0mmol), triethylamine 0.53g (5.2mmol), 1,4-di

The 4.0 mL mixture of alkane was heated and stirred at 110° C. for 8 hours under a carbon monoxide environment (9.0 kg/cm ² ). After cooling at room temperature, ethyl acetate was added to remove insoluble materials by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 5: 1 to 2: 1) to obtain 0.21 g of the target product (yield 69%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.60 (1H, d), 7.10 (1H, d), 5.87 (1H, s), 3.85 (2H, q), 3.79 (3H, d), 3.54-3.41 (2H, m), 2.54 (3H, s), 1.25 (3H, t)

[Example 11]

4-fluoro-2-methyl-5-[1-methyl-3-(pentafluoroethyl)-1H-1,2,4-triazol-5-yl]benzoic acid ethyl ester (the compound of the present invention) Number: F-0078)

(1) Production of 1-methyl-3-(pentafluoroethyl)-1H-1,2,4-triazole-5-amine

A mixture of 5.00 g (36.5 mmol) of 1-amino-1-methylguanidine sulfate and 6.58 g (40.1 mmol) of perfluoropropionic acid was heated and stirred at 110° C. for 9 hours. After leaving to cool at room temperature, a saturated sodium bicarbonate aqueous solution was added to adjust to pH 8, extracted with ethyl acetate, and the resulting organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 4.86 g of crude target product (yield 62%). It is used directly in the next step without purification.

¹ H-NMR data (300MHz, CDCl ₃ /TMS δ(ppm)): 4.92(2H,s), 3.71(3H,s)

(2) Production of 5-bromo-1-methyl-3-(pentafluoroethyl)-1H-1,2,4-triazole

In 1-methyl-3-(pentafluoroethyl)-1H-1,2,4-triazol-5-amine 3.00g (13.9mmmol), copper (II) bromide 6.20g (27.8mmmol), acetonitrile Under ice-cooling, 25.0 mL of the mixture was added with 2.88 g (27.9 mmol) of tributyl nitrite, followed by heating and stirring at 60° C. for 3 hours. After cooling at room temperature, ethyl acetate was added, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3:1) to obtain 2.31 g of the target product (yield 59%).

¹ H-NMR data (300MHz, CDCl ₃ /TMS δ(ppm)): 4.00(3H,s)

(3) 4-fluoro-2-methyl-5-[1-methyl-3-(pentafluoroethyl)-1H-1,2,4-triazol-5-yl]benzoic acid ethyl ester (this Invention compound number: F-0078)

烷11.0mL、水1.6mL的混合物，在氮環 境下，添加二氯化[1,1’-雙(二苯基膦基)鐵莘]鈀(II)二氯甲烷加成物0.67g(0.82mmol)及5-乙氧基羰基-2-氟-4-甲基苯基硼酸2.50g(11.1mmol)，在70℃下加熱攪拌3.5小時。在室溫下放冷後，添加乙酸乙酯，將不溶物以過濾除去，將溶劑在減壓下餾去。將殘渣以氧化矽凝膠管柱層析法(展開溶劑，正己烷：乙酸乙酯=9：1)精製，得到目標物1.04g(產率33%)。 In 5-bromo-1-methyl-3-(pentafluoroethyl)-1H-1,2,4-triazole 2.30g (8.21mmol), potassium carbonate 3.41g (24.7mmol), 1,4-di

A mixture of 11.0 mL of alkane and 1.6 mL of water is added under a nitrogen atmosphere [1,1′-bis(diphenylphosphino)ferroxa]palladium (II) dichloromethane adduct 0.67 g (0.82 mmol) and 5-ethoxycarbonyl-2-fluoro-4-methylphenylboronic acid 2.50 g (11.1 mmol), heated and stirred at 70° C. for 3.5 hours. After cooling at room temperature, ethyl acetate was added to remove insoluble materials by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 9: 1) to obtain 1.04 g of the target product (yield 33%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.23 (1H, d), 7.15 (1H, d), 4.37 (2H, q), 3.94 (3H, d), 2.71 (3H, s), 1.39 (3H, t)

[Example 12]

(5-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)aminecarboxamide]phenyl)-1-methyl-1H-1,2,4- Production of tributyl-3-yl) (methyl) carbamic acid third butyl ester (the compound number of the present invention: D-00XX)

(1) 5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester (the compound number of the present invention) : Manufacturing of J-0042)

To a mixture of 31.59 g (102.5 mmol) of 2-fluoro-5-iodo-N,4-dimethylbenzoylhydrazine and 220 mL of toluene, add 13.55 g (225.6 mmol) of acetic acid and ethyl thioglufolate 15.02 g (112.8mmol), heated to reflux for 6 hours. After cooling at room temperature, the solvent was distilled off, extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3:2) to obtain 25.88 g of the target product (yield 65%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.10 (1H, d), 7.13 (1H, d), 4.51 (2H, q), 3.93 (3H, d), 2.51 (3H, s), 1.45 (3H, t)

(2) 5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazole-3-carboxy Production of acid (Compound No. of the present invention: J-0043)

In 5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester 10.00g (25.70mmol), tetrahydrofuran A mixture of 40 mL, 20 mL of ethanol, and 20 mL of water was added with 3.23 g (76.98 mmol) of lithium hydroxide monohydrate, and stirred at room temperature for 23 hours. After the reaction was completed, ethyl acetate was added. After liquid separation, a 10% citric acid aqueous solution was added to the resulting aqueous layer to make it acidic, followed by extraction with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 7.12 g of the target product (yield 77%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.10 (1H, d), 7.16 (1H, d), 3.96 (3H, d), 2.52 (3H, s)

(3) [5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazol-3-yl]carbamic acid tert-butyl ester ( Production of the compound number of the present invention: J-0049)

In 5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazole-3-carboxylic acid 7.12g (19.7mmol), triethylamine After a mixture of 2.39 g (23.6 mmol) and 100 mL of third butanol was added 6.51 g (23.6 mmol) of diphenylphosphoryl azide at room temperature, the mixture was heated under reflux for 4 hours. After cooling at room temperature, it was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 7: 3 to 3: 2) to obtain 5.94 g of the target product (yield) 70%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.98 (1H, d), 7.11 (1H, d), 7.08 (1H, s), 3.79 (3H, d), 2.49 (3H, s),1.53(9H,s)

(4) 5-{3-[(third butoxycarbonyl)amino]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro-2-methyl Production of methyl benzoate (Compound No. of the present invention: F-0661)

The third butyl [5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazol-3-yl]carbamic acid 5.94g ( 13.74mmol), [1,1'-bis(diphenylphosphino)ironxin] palladium (II) dichloromethane adduct 0.11g (0.13mmol), triethylamine 2.78g (27.5mmol) A mixture of 60 mL of methanol was heated and stirred at 100° C. for 5 hours under a carbon monoxide environment (9.0 kg/cm ² ). After leaving to cool at room temperature, ethyl acetate was added to remove insoluble materials by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3: 2 to 1:1) to obtain 4.36 g of the target product (yield 87%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.19 (1H, d), 7.12 (1H, d), 7.06 (1H, s), 3.89 (3H, s), 3.80 (3H, d), 2.69(3H,s), 1.53(9H,s)

(5) 5-{3-[(third butoxycarbonyl)(methyl)amino]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro- Production of methyl 2-methylbenzoate (the compound number of the present invention: F-0662)

In 5-{3-[(third butoxycarbonyl)amino]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro-2-methylbenzoic acid A mixture of 0.98 g (2.7 mmol) of methyl ester, 0.76 g (5.4 mmol) of methyl iodide and 10.8 mL of N,N-dimethylformamide was added 0.12 g (3.0 mmol of sodium hydride) at room temperature, converted to 60% purity ), stirring at the same temperature for 3 hours. After adding water to the reaction mixture, it was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.10 g of crude target product (yield: 100%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.22 (1H, d), 7.11 (1H, d), 3.89 (3H, s), 3.80 (3H, d), 3.36 (3H, s), 2.69(3H,s), 1.53(9H,s)

(6) 5-{3-[(third butoxycarbonyl)(methyl)amino]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro- Production of 2-methylbenzoic acid (the compound number of the present invention: G-0655)

In crude 5-{3-[(third butoxycarbonyl)(methyl)amino]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro- A mixture of 1.10 g (calculated as 2.7 mmol) of methyl 2-methylbenzoate, 10 mL of tetrahydrofuran, 5 mL of ethanol, and 5 mL of water was added with 0.34 g (8.1 mmol) of lithium hydroxide monohydrate, and stirred at room temperature for 4 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. After adding a 10% citric acid aqueous solution to make it acidic, it was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.98 g of the target product (yield: 100%).

¹ H-NMR data (300 MHz, DMSO-d ₆ /TMS δ (ppm)): 8.07 (1H, d), 7.47 (1H, d), 3.75 (3H, d), 3.19 (3H, s), 2.63 ( 3H,s),1.42(9H,s)

(7) (5-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)aminecarboxamido]phenyl}-1-methyl-1H-1,2 , 4-triazol-3-yl) (methyl) carbamic acid third butyl ester (Compound No. of the present invention: D-0011)

In 5-{3-[(third butoxycarbonyl)(methyl)amino]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro-2- To a mixture of 0.98 g (2.7 mmol) of toluic acid, 10 mL of tetrahydrofuran, and 10 mL of chloroform, add 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride 0.62 g (3.2 mmol) 1. 0.44 g (2.9 mmol) of 1-hydroxybenzotriazole monohydrate and 0.62 g (6.3 mmol) of 2,2,2-trifluoroethylamine were stirred overnight at room temperature. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated aqueous sodium bicarbonate solution, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3: 2 to 1:1) to obtain 0.96 g of the target product (yield) 80%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.70 (1H, d), 7.11 (1H, d), 6.63 (1H, t), 4.19-4.00 (2H, m), 3.80 ( 3H,d), 3.35(3H,s), 2.54(3H,s), 1.53(9H,s)

[Example 13]

5-(3-cyano-1-methyl-1H-1,2,4-triazol-5-yl)-4-fluoro-2-methyl-N-(2,2,2-trifluoroethane Base) benzamide (the compound number of the present invention: A-0374)

(1) 5-{3-[(third butoxycarbonyl)amino]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro-2-methyl Production of benzoic acid (Compound No. of the present invention: G-0654)

In 5-{3-[(third butoxycarbonyl)amino]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro-2-methylbenzoic acid A mixture of 3.28 g (9.00 mmol) of methyl ester, 30 mL of tetrahydrofuran, 15 mL of ethanol, and 15 mL of water was added with 1.13 g (26.9 mmol) of lithium hydroxide monohydrate, and stirred at room temperature for 4 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. After adding 1 M citric acid aqueous solution to make it acidic, it was extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 3.15 g of the target product (yield: 100%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 9.18 (1H, s), 8.71 (1H, d), 7.14 (1H, d), 3.92 (3H, d), 2.78 (3H, s),1.58(9H,s)

(2)(5-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)aminecarboxamido]phenyl}-1-methyl-1H-1,2 , 4-triazol-3-yl) carbamic acid third butyl ester (the compound number of the present invention: D-0008)

In 5-{3-[(third butoxycarbonyl)amino]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro-2-methylbenzoic acid 3.15g (8.99mmol), tetrahydrofuran 50mL, chloroform 30mL mixture was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride 2.07g (10.8mmol), 1-hydroxyl Benzotriazole monohydrate 1.45 g (9.47 mmol) and 2,2,2-trifluoroethylamine 2.27 g (22.9 mmol) were stirred at room temperature overnight. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated aqueous sodium bicarbonate solution, water, and saturated brine to remove Water magnesium sulfate drying. The solvent was distilled off under reduced pressure to obtain 3.82 g of crude target product (yield 98%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.68 (1H, d), 7.17 (1H, s), 7.12 (1H, d), 6.53 (1H, s), 4.16-4.01 ( 2H, m), 3.79 (3H, d), 2.54 (3H, s), 1.53 (9H, s)

(3) 5-(3-amino-1-methyl-1H-1,2,4-triazol-5-yl)-4-fluoro-2-methyl-N-(2,2,2- Production of trifluoroethyl) benzamide (compound number of the present invention: D-0001)

In (5-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)aminecarboxamide]phenyl}-1-methyl-1H-1,2,4 -A solution of 3.85 g (8.92 mmol) of tributyl-3-yl)carbamate in chloroform (35 mL) was added with 3.0 mL (39 mmol) of trifluoroacetic acid and heated to reflux for 3 hours. After cooling at room temperature, the solvent was distilled off, followed by extraction with chloroform, and the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 2.54 g of the target product (yield 86%).

¹ H-NMR data (300 MHz, DMSO-d ₆ /TMS δ (ppm)): 9.12 (1H, t), 7.52 (1H, d), 7.39 (1H, d), 5.39 (2H, s), 4.17- 3.97(2H,m), 3.55(3H,d), 2.41(3H,s)

(4) 5-(3-cyano-1-methyl-1H-1,2,4-triazol-5-yl)-4-fluoro-2-methyl-N-(2,2,2- Production of trifluoroethyl) benzamide (compound number of the present invention: A-0374)

In 5-(3-amino-1-methyl-1H-1,2,4-triazol-5-yl)-4-fluoro-2-methyl-N-(2,2,2-trifluoro Ethyl) benzamide 0.20g (0.60mmol), copper cyanide 0.11g (1.2mmol), acetonitrile 3.0mL mixture was added at room temperature third nitrite 0.18g (1.7mmol), in 60 Heat and stir at ℃ for 3 hours. After cooling at room temperature, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Distill off the solvent under reduced pressure, The residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1:1 to 1:2) to obtain 59.1 mg of the target product (yield 29%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.67 (1H, d), 7.19 (1H, d), 6.28 (1H, s), 4.18-4.03 (2H, m), 3.94 ( 3H, d), 2.56 (3H, s)

[Example 14]

5-{3-[(benzyloxy)methyl]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro-2-methyl-N-(2 , 2,2-Trifluoroethyl) Benzoamide (Compound No. of the Invention: A-0415)

(1) [5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazol-3-yl)methanol (the compound number of the present invention) : J-0044) manufacturing

In 5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester 5.40g (13.9mmol), tetrahydrofuran A mixture of 47 mL and 35 mL of ethanol was added with 0.53 g (13.9 mmol) of sodium boron hydride, and stirred at room temperature for 20 hours. After adding a citric acid aqueous solution to the reaction mixture, it was extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 4.21 g of crude target product (yield) 87%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.03 (1H, d), 7.13 (1H, d), 4.79 (2H, s), 3.82 (3H, d), 2.50 (3H, s), 2.35(1H, s)

(2) 3-[(benzyloxy)methyl]-5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazole (Compound No. of the present invention: J-0045)

In [5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazol-3-yl)methanol 3.21g (9.25mmol), bromine A mixture of 1.66 g (9.71 mmol) of benzyl group and 10 mL of N,N-dimethylformamide was added under ice-cooling 0.39 g (9.8 mmol, converted to 60% purity) of sodium hydride, and stirred at room temperature for 1 hour half. After adding water to the reaction mixture, it was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residual The residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 4: 1 to 7: 3) to obtain 2.80 g of the target product (yield 69%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.05 (1H, d), 7.43-7.28 (5H, m), 7.12 (1H, d), 4.71 (2H, s), 4.63 ( 2H,s), 3.83(3H,d), 2.49(3H,s)

(3) 5-{3-[(benzyloxy)methyl]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro-2-methylbenzoic acid Production of methyl ester (Compound No. of the present invention: F-0131)

3-[(Benzyloxy)methyl]-5-(2-fluoro-5-iodo-4-methylphenyl)-1-methyl-1H-1,2,4-triazole 2.80g (6.40mmol), [1,1'-bis(diphenylphosphino)ironxin] palladium (II) dichloromethane adduct 52.3mg (0.0640mmol), triethylamine 1.30g (12.8mmol) ), a mixture of 40 mL of methanol is heated and stirred at 100° C. for 5 hours under a carbon monoxide environment (9.0 kg/cm ² ). After leaving to cool at room temperature, ethyl acetate was added to remove insoluble materials by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3:2) to obtain 2.36 g of the target product (yield 100%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 8.25 (1H, d), 7.47-7.26 (5H, m), 7.12 (1H, d), 4.71 (2H, s), 4.65 ( 2H,s), 3.89(3H,s), 3.84(3H,d), 2.69(3H,s)

(4) 5-{3-[(benzyloxy)methyl]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro-2-methylbenzoic acid (Compound No. of the present invention: G-0128)

Methyl 5-{3-[(benzyloxy)methyl]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro-2-methylbenzoate A mixture of 2.20 g (5.96 mmol), 10 mL of tetrahydrofuran, 5 mL of ethanol, and 5 mL of water was added with 0.75 g (18 mmol) of lithium hydroxide monohydrate, and stirred at room temperature for 1 hour. After the reaction was completed, the solvent was distilled off under reduced pressure, 1M hydrochloric acid was added to make it acidic, extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. Reduce the solvent Distillation was carried out under reduced pressure to obtain 1.94 g of the target product (yield 92%).

¹ H-NMR data (300 MHz, DMSO-d ₆ /TMS δ (ppm)): 8.09 (1H, d), 7.47 (1H, d), 7.40-7.25 (5H, m), 4.60 (2H, s), 4.54(2H,s), 3.79(3H,d), 2.64(3H,s)

(5) 5-{3-[(benzyloxy)methyl]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro-2-methyl-N -Production of (2,2,2-trifluoroethyl)benzamide (Compound No. of the present invention: A-0415)

In 5-{3-[(benzyloxy)methyl]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro-2-methylbenzoic acid 1.80g (5.07mmol), tetrahydrofuran 20mL, chloroform 10mL mixture was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride 1.17g (6.10mmol), 1-hydroxybenzo Triazole monohydrate 0.82g (5.4mmol) and 2,2,2-trifluoroethylamine 1.28g (12.9mmol) were stirred at room temperature overnight. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with saturated aqueous sodium bicarbonate solution, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 3: 2 to 3: 7) to obtain 2.04 g of the target product (yield) 92%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.69 (1H, d), 7.43-7.26 (5H, m), 7.11 (1H, d), 6.58 (1H, t), 4.69 ( 2H,s),4.62(2H,s),4.16-4.00(2H,m),3.82(3H,d),2.54(3H,s)

[Example 15]

4-fluoro-2-methyl-5-[1-methyl-3-(phenoxymethyl)-1H-1,2,4-triazol-5-yl]-N-(2,2, 2-Trifluoroethyl) Benzoamide (Compound No. of the Invention: A-0413)

(1) 4-fluoro-5-[3-(hydroxymethyl)-1-methyl-1H-1,2,4-triazol-5-yl]-2-methyl -N-(2,2,2-trifluoroethyl)benzamide (Compound No. of the present invention: A-0408)

5-{3-[(benzyloxy)methyl]-1-methyl-1H-1,2,4-triazol-5-yl}-4-fluoro-2-methyl-N-( 2,2,2-trifluoroethyl)benzamide 0.32g (0.73mmol), 10% Pd/C0.03g, and a mixture of 10mL of ethanol under a hydrogen atmosphere (atmospheric pressure) and stirred at room temperature for 15 hours . After the reaction was completed, it was filtered through celite, and the solvent was distilled off under reduced pressure to obtain 0.24 g of the target product (yield 95%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.79 (1H, d), 7.57 (1H, t), 7.10 (1H, d), 5.98 (1H, t), 4.71 (2H, d), 4.19-3.99 (2H, m), 3.86 (3H, d), 2.57 (3H, s)

(2) 4-fluoro-2-methyl-5-[1-methyl-3-(phenoxymethyl)-1H-1,2,4-triazol-5-yl]-N-(2 , 2,2-Trifluoroethyl) Benzoamide (Compound No. of the Invention: A-0413)

In 4-fluoro-5-[3-(hydroxymethyl)-1-methyl-1H-1,2,4-triazol-5-yl]-2-methyl-N-(2,2,2 -A mixture of 0.20 g (0.58 mmol) of trifluoroethyl)benzamide, 0.23 g (0.88 mmol) of triphenylphosphine, 0.08 g (0.9 mmol) of phenol, and 3.0 mL of tetrahydrofuran. Under ice cooling, add azobis After 0.18 g (0.89 mmol) of diisopropyl formate, it was stirred at room temperature for 18 hours. After the reaction was completed, water was added and extracted with ethyl acetate, and the resulting organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent, n-hexane: ethyl acetate = 1:1) to obtain 0.18 g of the target product (yield 74%).

¹ H-NMR data (300 MHz, CDCl ₃ /TMS δ (ppm)): 7.69 (1H, d), 7.30 (2H, t), 7.16-6.95 (4H, m), 6.44 (1H, t), 5.16 ( 2H,s), 4.17-4.01(2H,m), 3.85(3H, d), 2.54(3H,s)

The physical property values of the compound [I] of the present invention synthesized according to the foregoing examples are shown in Tables 78 to 93 below including the values in the foregoing examples, and the physical property values of the compound [II] of the present invention are also shown in In Table 94 to Table 104, the physical property values of the compound [III] of the present invention are also shown in Table 105 to Table 110. In addition, the compound numbers and symbols in the table have the same meaning as described above.

Next, specific examples of the preparation of the pest control agent of the present invention will be described. The pest control agent is derived from the 5-(1,2,4-triazol-5-yl)benzamide of the present invention manufactured as described above. Thing or its agriculturally acceptable salt. However, the types and compounding ratios of compounds and additives are not limited to these, and can be changed within a wide range. In addition, in the following description, "part" means a mass part.

[Formulation Example 1] Emulsion

Dissolve the above uniformly into an emulsion.

[Formulation Example 2] Water and agent

The above is uniformly mixed and pulverized into water and agent.

[Formulation Example 3] Powder

The above is uniformly mixed and pulverized into a powder.

[Formulation Example 4] Granules

Mix and crush the above uniformly. Add 20 parts of water to this mixture and knead so that After being processed into 14 to 32 mesh granules with an extrusion granulator, it is dried into granules.

[Formulation Example 5] Suspension

After mixing the above with a high-speed mixer for 30 minutes, it is pulverized with a wet pulverizer to form a suspending agent.

[Formulation Example 6] Granule water and agent

The above mixture is kneaded and granulated. The obtained granules were dried with a fluidized bed dryer to obtain granule water and agent.

Next, the effect of the pest control agent of the present invention will be described with test examples.

[Experiment example 1] Plutella xylostella insecticidal activity test

The water and the agent prepared according to Formulation Example 2 were released to a concentration of 500 ppm with methene to the active ingredient. Soak the cabbage leaves in this medicine, air dry, and put in a plastic cup. Ten second-instar larvae of Plutella xylostella (Plutella xylostella) were released and capped. After that, it was placed in a constant temperature room at 25°C, and the number of dead insects was checked 6 days later, and the dead insect rate was determined by the calculation formula of number 1. The test is conducted in 1 series.

【Number 1】

From this test, the compound numbers of compounds with a death rate of 90% or more are listed below.

A-0003, A-0022, A-0400, A-0441, A-0478, A-0524, B-0036, B-0039, B-0040, B-0125, B-0396, B-0402, B- 0408, B-0548, B-0560, B-0562, B-0567, B-0574, B-0610, B-0688, B-0742, B-0744, B-0754, B-0760, B-0766, B-0767, B-0768, B-0771, B-0777, B-0784, B-0801, B-0805, B-0806, B-0829, B-0830, B-0831, B-0860, B- 0900, B-0909, B-0924, B-0927, B-0930, B-0969, B-0972, B-0975, B-1004, B-1009, B-1010, B-1012, B-1017, B-1032, B-1036, B-1042, B-1044, B-1056, B-1065, B-1066, B-1070, C-0038, D-0008, E-0001, E-0008, E- 0015, F- 0160, F-0368, F-0373, F-0382, F-0393, G-0248, G-0314, H-0003, H-0004, H-0007, H-0008, J-0017, J-0023

[Test Example 2] Nilaparvata lugens stal insecticidal activity test

The water and the agent prepared according to Formulation Example 2 were released to a concentration of 500 ppm with methene to the active ingredient. In its liquid medicine, the germinated rice is impregnated and put in a plastic cup. In this plastic cup, 10 second-instar larvae of brown planthopper (Nilaparvata lugens stal) were released and covered. After that, it was placed in a constant temperature room at 25°C, and the number of dead insects was checked 6 days later, and the dead insect rate was obtained from the calculation formula of number 1. The test is conducted in 1 series.

Using the compound number Ibh-8 described in International Publication No. 2015/150442 as a comparative compound, the same test as above was carried out. The structure of the comparative compound is as follows.

International Publication No. 2015/150442

The compound numbers of the compounds whose death rate is 90% or more by this test are listed below.

A-0003, A-0008, A-0022, A-0077, A-0254, A-0255, A-0256, A-0263, A-0264, A-0265, A-0286, A-0345, A- 0346, A-0360, A-0400, A-0402, A-0410, A-0419, A-0422, A-0423, A-0446, B-0002, B- 0003, B-0012, B-0018, B-0021, B-0025, B-0027, B-0033, B-0036, B-0055, B-0084, B-0125, B-0200, B-0209, B-0223, B-0298, B-0391, B-0400, B-0401, B-0402, B-0405, B-0435, B-0436, B-0487, B-0523, B-0526, B- 0560, B-0577, B-0580, B-0584, B-0592, B-0601, B-0604, B-0607, B-0610, B-0616, B-0632, B-0633, B-0635, B-0638, B-0639, B-0651, B-0654, B-0655, B-0656, B-0673, B-0676, B-0688, B-0691, B-0694, B-0697, B- 0700, B-0703, B-0706, B-0718, B-0721, B-0727, B-0730, B-0733, B-0741, B-0748, B-0754, B-0757, B-0760, B-0765, B-0766, B-0767, B-0768, B-0771, B-0784, B-0785, B-0788, B-0799, B-0800, B-0801, B-0805, B- 0806, B-0823, B-0838, B-0857, B-0873, B-0879, B-0900, B-0906, B-0909, B-0912, B-0924, B-0927, B-0972, B-0975, B-1006, B-1015, B-1017, B-1019, B-1022, B-1044, B-1054, B-1056, B-1060, C-0007, C-0017, C- 0023, C-0027, C-0028, D-0011, D-0012, E-0001, E-0008, E-0015, F-0056, F-0355, F-0368, F-0373, F-0393, F-0423, F-0429, F-0504, F-0524, G-0076, G-0290, G-0366, G-0386, H-0004, J-0020, J-0023, J-0027, J- 0035, J-0050, J-0053

On the other hand, the comparative compound Ibh-8 (described in International Publication No. 2015/150442) showed no activity at a concentration of 50 ppm.

[Test Example 3] Experiment on the control effect of Tetranychus urticae

According to the preparation example 2, the water and the agent were prepared so that methene was released to a concentration of 500 ppm as the active ingredient. In its liquid medicine, the soybean seedlings inoculated with 35 female adults of Tetranychus urticae in advance were dipped and air-dried. The treated soybean seedlings were placed in a constant temperature room at 25°C, and the number of surviving insects of female adults was checked 13 days later, and the control price was obtained from the calculation formula of number 2. The test is conducted in 1 series.

【Number 2】

Using the compound number Ibh-8 described in International Publication No. 2015/150442 as a comparative compound, the same test as above was carried out.

From this test, the compound numbers indicating the compounds with a control value of 90 or more are listed below.

A-0003, A-0008, A-0022, A-0077, A-0254, A-0255, A-0256, A-0286, A-0331, A-0345, A-0346, A-0359, A- 0360, A-0361, A-0397, A-0402, A-0410, A-0419, A-0422, A-0446, A-0496, A-0498, B-0003, B-0012, B-0017, B-0018, B-0021, B-0024, B-0025, B-0027, B-0028, B-0032, B-0033, B-0036, B-0044, B-0046, B-0078, B- 0091, B-0124, B-0125, B-0200, B-0209, B-0223, B-0289, B-0298, B-0312, B-0395, B-0396, B-0399, B-0400, B-0401, B-0402, B-0403, B-0404, B-0405, B-0408, B-0440, B-0443, B-0487, B-0488, B-0489, B-0523, B- 0526, B-0545, B-0548, B-0550, B-0559, B-0577, B-0580, B-0583, B-0584, B-0585, B-0592, B-0601, B-0604, B-0607, B-0610, B-0616, B-0631, B-0632, B-0634, B-0635, B-0636, B-0638, B-0639, B-0654, B-0655, B- 0656, B-0663, B-0673, B-0676, B-0679, B-0688, B-0691, B-0694, B-0697, B-0700, B-0703, B-0706, B-0718, B-0721, B-0724, B-0727, B-0730, B-0733, B-0741, B-0742, B-0743, B-0745, B-0748, B-0754, B-0757, B- 0760, B-0765, B-0766, B-0767, B-0768, B-0771, B- 0783, B-0784, B-0785, B-0788, B-0799, B-0800, B-0805, B-0806, B-0820, B-0823, B-0826, B-0829, B-0830, B-0838, B-0855, B-0856, B-0857, B-0858, B-0860, B-0876, B-0879, B-0897, B-0900, B-0903, B-0924, B- 0927, B-0930, B-0972, B-0975, B-0978, B-1001, B-1004, B-1007, B-1008, B-1012, B-1013, B-1014, B-1015, B-1016, B-1017, B-1019, B-1020, B-1022, B-1056, B-1064, B-1065, B-1070, B-1074, B-1075, B-1086, B- 1088, C-0007, C-0017, C-0027, C-0028, C-0039, D-0001, D-0008, D-0009, D-0010, D-0012, E-0001, E-0008, E-0015, G-0076, G-0290, G-0392, J-0023

On the other hand, the comparative compound Ibh-8 (described in International Publication No. 2015/150442) showed no activity at a concentration of 50 ppm.

[Test Example 4] Nacobbus aberrans (Nacobbus aberrans) inhibition of nematode activity test

The test compound was dissolved in N,N-dimethylformamide containing 1% of tween20, and the solution was released into a concentration of 20 ppm of the active ingredient with methene. 0.5 ml of the drug solution was mixed with 0.5 ml of the suspension containing approximately 30 larvae of the second stage of pseudo-rhizobia (Nacobbus aberrans) to a concentration of 10 ppm of the active ingredient, and placed in a constant temperature room at 25°C. After 5 days, the number of viable nematodes was counted under a microscope, and the nematode-inhibiting activity was determined from the calculation formula of number 3. The test is conducted in 2 series.

【Number 3】

Use the compound number Ibh-8 described in International Publication No. 2015/150442 as The compounds were compared and the same test as above was carried out.

From this test, the compound numbers of compounds that inhibited nematode rate by 90% or more are listed below.

A-0003, A-0008, A-0022, A-0077, A-0254, A-0255, A-0256, A-0263, A-0268, A-0286, A-0301, A-0331, A- 0344, A-0345, A-0346, A-0359, A-0360, A-0361, A-0374, A-0385, A-0402, A-0410, A-0419, A-0422, A-0435, A-0460, B-0002, B-0003, B-0012, B-0017, B-0018, B-0021, B-0022, B-0027, B-0028, B-0032, B-0033, B- 0034, B-0035, B-0036, B-0044, B-0055, B-0060, B-0084, B-0091, B-0109, B-0200, B-0209, B-0223, B-0298, B-0312, B-0390, B-0391, B-0392, B-0399, B-0400, B-0401, B-0402, B-0403, B-0404, B-0405, B-0408, B- 0435, B-0439, B-0440, B-0441, B-0442, B-0443, B-0487, B-0488, B-0489, B-0523, B-0526, B-0529, B-0545, B-0560, B-0562, B-0574, B-0577, B-0580, B-0583, B-0585, B-0592, B-0604, B-0607, B-0610, B-0633, B- 0638, B-0639, B-0653, B-0654, B-0655, B-0656, B-0673, B-0676, B-0679, B-0688, B-0691, B-0694, B-0697, B-0700, B-0703, B-0706, B-0718, B-0721, B-0724, B-0730, B-0733, B-0741, B-0742, B-0743, B-0744, B- 0745, B-0748, B-0751, B-0754, B-0757, B-0760, B-0765, B-0766, B-0767, B-0768, B-0774, B-0783, B-0784, B-0796, B-0801, B-0805, B-0806, B-0815, B-0826, B-0829, B-0830, B-0831, B-0855, B-0856, B-0857, B- 0873, B-0879, B-0903, B-0909, B-0912, B-0924 , B-0927, B-0930, B-0975, B-0978, B-1001, B-1004, B-1007, B-1009, B-1010, B-1012, B-1013, B-1014, B -1015, B-1018, B-1019, B- 1020, B-1022, B-1024, B-1032, B-1042, B-1044, B-1054, B-1056, B-1058, B-1064, B-1065, B-1066, B-1070, B-1075, B-1078, B-1085, B-1086, B-1087, B-1088, C-0007, C-0017, C-0023, C-0028, C-0029, C-0037, C- 0038, C-0039, D-0012, E-0008, E-0015

On the other hand, the comparative compound Ibh-8 (described in International Publication No. 2015/150442) showed no activity at a concentration of 10 ppm.

[Industry availability]

The present invention provides a novel compound with excellent insecticidal activity and an intermediate for its production, which is useful in the field of pesticides and agriculture and has industrial applicability.

Claims (14)

A 5-(1,2,4-triazol-5-yl)benzamide derivative represented by the following general formula [I] or its agriculturally acceptable salt,

In the formula, n represents an integer of 0, 1, or 2, m represents an integer of 0, 1, or 2, A means oxygen atom or sulfur atom, B represents a single bond, radical -O-, radical -S(=O) _m -or radical -N(-R ⁷ )-, R ¹ and R ² each independently represent a hydrogen atom, C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkyl, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl, C ₂ to C ₆ Alkynyl, C ₂ to C ₆ alkenyl, C ₂ to C ₆ haloalkynyl, C ₂ to C ₆ haloalkenyl, C ₁ to C ₆ alkoxy, C ₁ to C ₆ haloalkoxy, C ₁ To C ₆ haloalkyl, C ₃ to C ₆ halocycloalkyl, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkyl, unsubstituted or monosubstituted by substituent group α Or polysubstituted phenyl, unsubstituted or substituted by substituent group α mono- or polysubstituted phenyl C ₁ to C ₃ alkyl, unsubstituted or substituted by substituent group α Monosubstituted or polysubstituted heteroaryl, unsubstituted or selected via substituent group α, monosubstituted or polysubstituted heteroaryl C ₁ to C ₃ alkyl, cyano, cyano C ₁ to C ₆ alkyl, cyano C ₃ to C ₆ cycloalkyl, C ₁ to C ₆ alkoxycarbonyl C ₃ to C ₆ cycloalkyl, hydroxy, hydroxy C ₁ to C ₆ alkyl, C ₁ to C ₆ Alkoxy C ₁ to C ₆ alkyl, methyl amide, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) amine, C ₁ to C ₆ alkyl Carbonyl, C ₁ to C ₆ alkoxy C ₁ to C ₆ alkylcarbonyl, C ₃ to C ₆ cycloalkylcarbonyl, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkylcarbonyl, C ₁ to C ₆ alkoxycarbonyl, aminecarboxamide, mono(C ₁ to C ₆ alkyl)aminocarbonyl, di(C ₁ to C ₆ alkyl)aminocarbonyl, C ₁ to C ₆ alkoxycarbonyl C ₁ to C ₆ alkylamino groups, mono (C ₁ to C ₆ alkoxycarbonyl) amine groups, unsubstituted or substituted groups selected through substituent group α, mono- or poly-substituted phenylcarbonyl groups, (C ₁ to C ₆ alkylthio) carbonyl, (C ₁ to C ₆ alkyl) thiocarbonyl, (C ₁ to C ₆ alkoxy) thiocarbonyl, amine thiocarboxamide, mono (C ₁ to C ₆ alkyl)aminothiocarbonyl, di(C ₁ to C ₆ alkyl)aminothiocarbonyl, C ₁ to C ₆ alkylsulfonyl, C ₁ to C ₆ haloalkylsulfonyl, amine Sulfonyl, mono(C ₁ to C ₆ alkyl)aminosulfonyl, di(C ₁ to C ₆ alkyl)aminosulfonyl, C ₁ to C ₆ alkoxycarbonyl C ₁ to C ₆ Alkyl, aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₃ to C ₆ cycloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ haloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, di (C ₁ to C ₆ alkyl) aminocarbonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylcarbonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylcarbonyl C ₁ to C ₆ alkyl, hydroxyimino group, C ₁ to C ₆ alkoxyimino group, Hydroxyimino group C ₁ To C ₆ alkyl, C ₁ to C ₆ alkoxyimino C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkoxy imino C ₁ to C ₆ alkyl, heterocycloalkyl, Or heterocycloalkyl C ₁ to C ₆ alkyl, and R ¹ and R ² may also form a 3 to 8 membered heterocyclic ring together with the nitrogen atoms to which they are bonded, or have 1 to 4 selected from Heterocyclic ring of 3 to 8 members of hetero atom of oxygen atom, sulfur atom and nitrogen atom, the heterocyclic ring can also be halogen atom, cyano group, nitro group, C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkoxy group Group, C ₁ to C ₆ haloalkyl or pendant oxygen substitution, R ³ represents a halogen atom, cyano group, C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkyl group, hydroxyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ alkylthio group, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ alkylsulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) amine, amine Formyl or thiocarbamoyl, R ⁴ represents a halogen atom, cyano group, nitro group, C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkoxy group C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkylthio group C ₁ to C ₆ Alkyl, cyano C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkyl, C ₃ to C ₆ cycloalkyl, C ₃ to C ₆ halocycloalkyl, C ₂ to C ₆ alkenyl, C ₂ to C ₆ haloalkenyl, C ₂ to C ₆ alkynyl, C ₂ to C ₆ haloalkynyl, hydroxy, C ₁ to C ₆ alkoxy, C ₁ to C ₆ haloalkoxy, C ₁ to C ₆ alkylthio, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ haloalkylthio, C ₁ to C ₆ haloalkylsulfinyl Acyl, C ₁ to C ₆ haloalkyl sulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) amine, amine formyl or amine Thiomethyl, R ⁵ represents a hydrogen atom, halogen atom, cyano group, C ₁ to C ₆ alkyl group, C ₃ to C ₆ cycloalkyl group, C ₃ to C ₆ cycloalkyl group C ₁ to C ₆ alkyl group, C ₂ to C ₆ Alkenyl, C ₃ to C ₆ cycloalkyl C ₂ to C ₆ alkenyl, C ₂ to C ₆ alkynyl, C ₃ to C ₆ cycloalkyl C ₂ to C ₆ alkynyl, C ₁ to C ₆ haloalkane Group, C ₃ to C ₆ halocycloalkyl, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkyl, C ₂ to C ₆ haloalkenyl, C ₂ to C ₆ haloalkynyl, hydroxyl, amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkylcarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ haloalkylcarbonyl) amine C ₁ to C ₆ alkyl Group, mono (C ₃ to C ₆ cycloalkylcarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkoxycarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ To C ₆ alkyl)aminocarbonylamino C ₁ to C ₆ alkyl, di(C ₁ to C ₆ alkyl)aminocarbonylamino C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkyl) Sulfosulfonyl)amino C ₁ to C ₆ alkyl, mono(C ₁ to C ₆ haloalkylsulfonyl) amino C ₁ to C ₆ alkyl, N-(C ₁ to C ₆ alkylsulfonate Acyl)-N-(C ₁ to C ₆ alkyl)amine C ₁ to C ₆ alkyl, N-(C ₁ to C ₆ haloalkylsulfonyl)-N-(C ₁ to C ₆ alkyl Group) amine group C ₁ to C ₆ alkyl, hydroxy C ₁ to C ₆ alkyl, C ₁ to C ₆ alkoxy C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkoxy C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkoxy C ₁ to C ₆ haloalkyl, C ₃ to C ₆ cycloalkoxy C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkoxy C ₁ to C ₆ alkyl groups, unsubstituted or mono- or poly-substituted phenyl substituted by substituent group α, unsubstituted or mono- or poly-substituted substituents selected by substituent group α Heteroaryl, unsubstituted or substituted by substituent group α mono- or polysubstituted phenyl C ₁ to C ₃ alkyl, unsubstituted or substituted by substituent group α mono-substituted Or polysubstituted phenyl C ₁ to C ₃ haloalkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroaryl C ₁ to C ₃ alkyl, unsubstituted or The substituents selected through the substituent group α are mono- or polysubstituted heteroaryl C ₁ to C ₃ haloalkyl, cyano C ₁ to C ₆ alkyl, unsubstituted or selected through the substituent group α Substituted mono- or poly-substituted phenoxy C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or poly-substituted heteroaryloxy C ₁ to C ₃ alkyl Phenyl, unsubstituted or selected via substituent group α, mono- or polysubstituted phenyl C ₁ to C 3 alkoxy C ₁ to C 3 alkyl, unsubstituted or selected via substituent group α Substituent Mono- or poly-substituted heteroaryl C ₁ to C 3 alkoxy C ₁ to C 3 alkyl, mercapto C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylthio C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfinyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylthio C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylsulfinyl C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylsulfonyl C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkane Alkylthio C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkylsulfinyl C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkylsulfonyl C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylthio C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylsulfinyl C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylsulfonate Acyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfonyloxy C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylcarbonylthio C ₁ to C ₃ alkyl, unsubstituted Phenylthio C ₁ to C3 alkyl substituted by the substituent selected by the substituent group α, unsubstituted or substituted by the substituent selected by the substituent group α Sulfenyl C ₁ to C ₃ alkyl, unsubstituted or substituted by the substituent group α, mono- or polysubstituted phenylsulfonyl C ₁ to C ₃ alkyl, unsubstituted or Heteroarylthio C ₁ to C3 alkyl substituted by substituents selected through substituent group α, unsubstituted or substituted monosubstituted or polysubstituted heteroaromatic groups selected through substituent group α Sulfonyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroarylsulfonyl C ₁ to C ₃ alkyl, unsubstituted Or mono- or poly-substituted phenyl C ₁ to C ₃ alkylthio C ₁ to C3 alkyl, unsubstituted or selected by substituent group α Substituted or polysubstituted phenyl C ₁ to C ₃ alkylsulfinyl C ₁ to C ₃ alkyl, unsubstituted or substituted by substituent group α, mono- or poly-substituted phenyl C ₁ To C ₃ alkylsulfonyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or multi-substituted heteroaryl C ₁ to C ₃ alkylthio C ₁ To C3 alkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroaryl C ₁ to C ₃ alkylsulfinyl C ₁ to C ₃ alkyl, unsubstituted Or a mono- or poly-substituted heteroaryl C ₁ to C ₃ alkylsulfonyl C ₁ to C ₃ alkyl, heterocycloalkyl C ₁ to C ₆ alkyl selected from the substituents selected through the substituent group α, C ₁ to C ₆ alkylcarbonyl C ₁ to C ₆ alkyl, unsubstituted or substituted via substituent group α, mono- or multi-substituted phenylcarbonyl C ₁ to C ₃ alkyl , Unsubstituted or selected via substituent group α, mono- or poly-substituted heteroarylcarbonyl C ₁ to C ₃ alkyl, hydroxycarbonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkoxy Alkylcarbonyl C ₁ to C ₃ alkyl, mono(C ₁ to C ₆ alkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono(C ₁ to C ₆ haloalkyl) aminocarbonyl C ₁ to C ₆ Alkyl, mono (C ₃ to C ₆ cycloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₃ to C ₆ halocycloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, di( C ₁ to C ₆ alkyl) Aminocarbonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylcarbonyloxy C ₁ to C ₃ alkyl, C ₁ to C ₆ haloalkylcarbonyloxy C ₁ To C ₃ alkyl, nitro, amine, methyl acetyl, C ₁ to C ₆ alkylcarbonyl, carboxy, C ₁ to C ₆ alkoxycarbonyl, amine methyl, mono(C ₁ to C ₆ alkyl Group) aminocarbonyl, mono(C ₁ to C ₆ haloalkyl) aminocarbonyl, di(C ₁ to C ₆ alkyl)aminocarbonyl, di(C ₁ to C ₆ haloalkyl)aminocarbonyl, Or (1,3-bi- pendant isoindoline-2-yl) C ₁ to C ₃ alkyl, in addition, R ⁵ and R ⁷ may also form together with these bonded nitrogen atoms 3 Heterocycle to 6 members, or 3 to 6 member heterocycle having 1 to 4 heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom, R ⁶ represents a hydrogen atom or a C ₁ to C ₆ alkyl group, R ⁷ represents a hydrogen atom, C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkyl, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl, C ₂ to C ₆ alkenyl, C ₂ to C ₆ alkynyl, methyl acetyl, C ₁ to C ₆ alkylcarbonyl, C ₁ to C ₆ alkoxycarbonyl, C ₁ to C ₆ alkylsulfonyl or C ₁ to C ₆ haloalkylsulfonyl , Substituent group α represents a halogen atom, C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkyl group, hydroxyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ haloalkoxy group, nitro group, Cyano, mercapto, C ₁ to C ₆ alkylthio, C ₁ to C ₆ haloalkylthio, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ haloalkylsulfinyl , C ₁ to C ₆ alkylsulfonyl, C ₁ to C ₆ haloalkylsulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) Amino, mono (C ₁ to C ₆ alkylsulfonyl) amine, mono (C ₁ to C ₆ haloalkylsulfonyl) amine, N-(C ₁ to C ₆ alkylsulfonyl) -N-(C ₁ to C ₆ alkyl)amino, N-(C ₁ to C ₆ haloalkylsulfonyl)-N-(C ₁ to C ₆ alkyl)amino, carboxamide, carboxyl , C ₁ to C ₆ alkylcarbonyl, C ₁ to C ₆ alkoxycarbonyl. A pesticide composition containing the 5-(1,2,4-triazol-5-yl)benzamide derivative described in item 1 of the scope of the patent application or containing it in agriculture Salt as an active ingredient. The pesticide composition as described in item 2 of the patent application scope, wherein the pesticide composition further contains a surfactant. A pest control agent, which contains the 5-(1,2,4-triazol-5-yl)benzamide derivative described in item 1 of the scope of the patent application or its agricultural application Allowable salts are used as active ingredients. The pest control agent as described in item 4 of the patent application scope, wherein the pest control agent is an insecticide, nematicide and acaricide. The pest control agent as described in item 5 of the patent application scope, the pest control agent is for paddy fields, dry fields, grasslands, orchards, non-agricultural land, greenhouses, nursery facilities, or plant factories where agricultural and horticultural plants are cultivated. Pests have the control effect. The pest control agent as described in item 6 of the patent application scope, wherein the plants for agricultural and horticultural purposes are plants conferred resistance by breeding methods or genetic recombination techniques. A pest control method using the 5-(1,2,4-triazol-5-yl)benzamide derivative described in item 1 of the patent application scope or its agricultural tolerance The amount of active ingredients in the salt. A method for controlling harmful organisms, which contains 5-(1,2,4-triazol-5-yl)benzamide derivatives described in item 1 of the scope of patent application or its agriculturally acceptable The permissible salt as an active ingredient of the pesticide composition is applied simultaneously or in batches to the agricultural or horticultural use or the place where the agricultural or horticultural use is to be cultivated or being cultivated. The pest control method as described in item 8 or item 9 of the patent application scope, wherein the place where the pest control agent is applied is paddy field, dry field, grassland, orchard, non-agricultural land, greenhouse, nursery facility, or plant factory. The pest control method as described in any one of the 8th to 10th items of the patent application scope, wherein the 5-(1,2,4-triazole- 5-yl) benzamide derivatives or their agriculturally acceptable salts are used as insecticides, nematicides and acaricides. A method for using a pest control agent, which uses the pest control agent described in any one of items 4 to 7 of the patent application range to control pests for agricultural and horticultural use. A 5-(1,2,4-triazol-5-yl)benzoic acid derivative represented by the following general formula [II] or a salt thereof,

In the formula, m represents an integer of 0, 1, or 2, n represents an integer of 0, 1, or 2, B represents a single bond, base-O-, base-S(=O)m- or base-N(-R ⁷ )-, R ³ represents a halogen atom, cyano group, C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkyl group, hydroxyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ alkylthio group, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ alkylsulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) amine, amine Formyl or thiocarbamoyl, R ⁴ represents a halogen atom, cyano group, nitro group, C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkoxy group C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkylthio group C ₁ to C ₆ Alkyl, cyano C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkyl, C ₃ to C ₆ cycloalkyl, C ₃ to C ₆ halocycloalkyl, C ₂ to C ₆ alkenyl, C ₂ to C ₆ haloalkenyl, C ₂ to C ₆ alkynyl, C ₂ to C ₆ haloalkynyl, hydroxy, C ₁ to C ₆ alkoxy, C ₁ to C ₆ haloalkoxy, C ₁ to C ₆ alkylthio, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ haloalkylthio, C ₁ to C ₆ haloalkylsulfinyl Acyl, C ₁ to C ₆ haloalkyl sulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) amine, amine formyl or amine Thiomethyl, R ⁵ represents a hydrogen atom, halogen atom, cyano group, C ₁ to C ₆ alkyl group, C ₃ to C ₆ cycloalkyl group, C ₃ to C ₆ cycloalkyl group C ₁ to C ₆ alkyl group, C ₂ to C ₆ Alkenyl, C ₃ to C ₆ cycloalkyl C ₂ to C ₆ alkenyl, C ₂ to C ₆ alkynyl, C ₃ to C ₆ cycloalkyl C ₂ to C ₆ alkynyl, C ₁ to C ₆ haloalkane Group, C ₃ to C ₆ halocycloalkyl, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkyl, C ₂ to C ₆ haloalkenyl, C ₂ to C ₆ haloalkynyl, hydroxyl, amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkylcarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ haloalkylcarbonyl) amine C ₁ to C ₆ alkyl Group, mono (C ₃ to C ₆ cycloalkylcarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkoxycarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ To C ₆ alkyl)aminocarbonylamino C ₁ to C ₆ alkyl, di(C ₁ to C ₆ alkyl)aminocarbonylamino C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkyl) Sulfosulfonyl)amino C ₁ to C ₆ alkyl, mono(C ₁ to C ₆ haloalkylsulfonyl) amino C ₁ to C ₆ alkyl, N-(C ₁ to C ₆ alkylsulfonate Acyl)-N-(C ₁ to C ₆ alkyl)amine C ₁ to C ₆ alkyl, N-(C ₁ to C ₆ haloalkylsulfonyl)-N-(C ₁ to C ₆ alkyl Group) amine group C ₁ to C ₆ alkyl, hydroxy C ₁ to C ₆ alkyl, C ₁ to C ₆ alkoxy C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkoxy C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkoxy C ₁ to C ₆ haloalkyl, C ₃ to C ₆ cycloalkoxy C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkoxy C ₁ to C ₆ alkyl groups, unsubstituted or mono- or poly-substituted phenyl substituted by substituent group α, unsubstituted or mono- or poly-substituted substituents selected by substituent group α Heteroaryl, unsubstituted or substituted by substituent group α mono- or polysubstituted phenyl C ₁ to C ₃ alkyl, unsubstituted or substituted by substituent group α mono-substituted Or polysubstituted phenyl C ₁ to C ₃ haloalkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroaryl C ₁ to C ₃ alkyl, unsubstituted or The substituents selected through the substituent group α are mono- or polysubstituted heteroaryl C ₁ to C ₃ haloalkyl, cyano C ₁ to C ₆ alkyl, unsubstituted or selected through the substituent group α Substituted mono- or poly-substituted phenoxy C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or poly-substituted heteroaryloxy C ₁ to C ₃ alkyl Phenyl, unsubstituted or selected via substituent group α, mono- or polysubstituted phenyl C ₁ to C 3 alkoxy C ₁ to C 3 alkyl, unsubstituted or selected via substituent group α Substituent Mono- or poly-substituted heteroaryl C ₁ to C 3 alkoxy C ₁ to C 3 alkyl, mercapto C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylthio C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfinyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylthio C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylsulfinyl C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylsulfonyl C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkane Alkylthio C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkylsulfinyl C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkylsulfonyl C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylthio C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylsulfinyl C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylsulfonate Acyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfonyloxy C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylcarbonylthio C ₁ to C ₃ alkyl, unsubstituted Phenylthio C ₁ to C3 alkyl substituted by the substituent selected by the substituent group α, unsubstituted or substituted by the substituent selected by the substituent group α Sulfenyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or poly-substituted phenylsulfonyl C ₁ to C ₃ alkyl, unsubstituted or Heteroarylthio C ₁ to C3 alkyl substituted by substituents selected through substituent group α, unsubstituted or substituted monosubstituted or polysubstituted heteroaromatic groups selected through substituent group α Sulfonyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroarylsulfonyl C ₁ to C ₃ alkyl, unsubstituted Or mono- or poly-substituted phenyl C ₁ to C ₃ alkylthio C ₁ to C ₃ alkyl, unsubstituted or selected by substituent group α Substituted or polysubstituted phenyl C ₁ to C ₃ alkylsulfinyl C ₁ to C ₃ alkyl, unsubstituted or substituted by substituent group α, mono- or poly-substituted phenyl C ₁ To C ₃ alkylsulfonyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or multi-substituted heteroaryl C ₁ to C ₃ alkylthio C ₁ To C3 alkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroaryl C ₁ to C ₃ alkylsulfinyl C ₁ to C ₃ alkyl, unsubstituted Or a mono- or poly-substituted heteroaryl C ₁ to C ₃ alkylsulfonyl C ₁ to C ₃ alkyl, heterocycloalkyl C ₁ to C ₆ alkyl selected from the substituents selected through the substituent group α, C ₁ to C ₆ alkylcarbonyl C ₁ to C ₆ alkyl, unsubstituted or substituted by a substituent group α, mono- or polysubstituted phenylcarbonyl C ₁ to C ₃ alkyl, Heteroarylcarbonyl C ₁ to C ₃ alkyl, hydroxycarbonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkoxy, unsubstituted or selected via substituent group α Carbonyl C ₁ to C ₃ alkyl, mono (C ₁ to C ₆ alkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ haloalkyl) aminocarbonyl C ₁ to C ₆ alkyl Group, mono (C ₃ to C ₆ cycloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₃ to C ₆ halocycloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, di (C ₁ to C ₆ alkyl) aminocarbonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylcarbonyloxy C ₁ to C ₃ alkyl, C ₁ to C ₆ haloalkylcarbonyloxy C ₁ to C ₃ alkyl, nitro, amine, carboxamide, C ₁ to C ₆ alkylcarbonyl, carboxy, C ₁ to C ₆ alkoxycarbonyl, amine carboxamide, mono (C ₁ to C ₆ alkyl )Aminocarbonyl, mono(C ₁ to C ₆ haloalkyl)aminocarbonyl, di(C ₁ to C ₆ alkyl)aminocarbonyl, di(C ₁ to C ₆ haloalkyl)aminocarbonyl, or (1,3-bi- pendant isoindoline-2-yl) C ₁ to C ₃ alkyl, in addition, R ⁵ and R ⁷ can also form 3 to 3 together with the nitrogen atoms to which they are bonded 6-membered heterocyclic ring, or 3 to 6-membered heterocyclic ring having 1 to 4 heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom, R ⁶ and R ⁸ each independently represent a hydrogen atom or a C ₁ to C ₆ alkyl group, R ⁷ represents a hydrogen atom, C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkyl, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl, C ₂ to C ₆ alkenyl, C ₂ to C ₆ alkynyl, methyl acetyl, C ₁ to C ₆ alkylcarbonyl, C ₁ to C ₆ alkoxycarbonyl, C ₁ to C ₆ alkylsulfonyl or C ₁ to C ₆ haloalkylsulfonyl , Substituent group α represents a halogen atom, C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkyl group, hydroxyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ haloalkoxy group, nitro group, Cyano, mercapto, C ₁ to C ₆ alkylthio, C ₁ to C ₆ haloalkylthio, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ haloalkylsulfinyl , C ₁ to C ₆ alkylsulfonyl, C ₁ to C ₆ haloalkylsulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) Amino, mono (C ₁ to C ₆ alkylsulfonyl) amine, mono (C ₁ to C ₆ haloalkylsulfonyl) amine, N-(C ₁ to C ₆ alkylsulfonyl) -N-(C ₁ to C ₆ alkyl)amino, N-(C ₁ to C ₆ haloalkylsulfonyl)-N-(C ₁ to C ₆ alkyl)amino, carboxamide, carboxyl , C ₁ to C ₆ alkylcarbonyl, C ₁ to C ₆ alkoxycarbonyl. A 5-phenyl-1,2,4-triazole derivative represented by the following general formula [III] or a salt thereof,

In the formula, m represents an integer of 0, 1, or 2, n represents an integer of 0, 1, or 2, B represents a single bond, base-O-, base-S(=O)m- or base-N(-R ⁷ )-, R ³ represents a halogen atom, cyano group, C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkyl group, hydroxyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ alkylthio group, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ alkylsulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) amine, amine Formyl or thiocarbamoyl, R ⁴ represents a halogen atom, cyano group, nitro group, C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkoxy group C ₁ to C ₆ alkyl group, C ₁ to C ₆ alkylthio group C ₁ to C ₆ Alkyl, cyano C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkyl, C ₃ to C ₆ cycloalkyl, C ₃ to C ₆ halocycloalkyl, C ₂ to C ₆ alkenyl, C ₂ to C ₆ haloalkenyl, C ₂ to C ₆ alkynyl, C ₂ to C ₆ haloalkynyl, hydroxy, C ₁ to C ₆ alkoxy, C ₁ to C ₆ haloalkoxy, C ₁ to C ₆ alkylthio, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ haloalkylthio, C ₁ to C ₆ haloalkylsulfinyl Acyl, C ₁ to C ₆ haloalkyl sulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) amine, amine formyl or amine Thiomethyl, R ⁵ represents a hydrogen atom, halogen atom, cyano group, C ₁ to C ₆ alkyl group, C ₃ to C ₆ cycloalkyl group, C ₃ to C ₆ cycloalkyl group C ₁ to C ₆ alkyl group, C ₂ to C ₆ Alkenyl, C ₃ to C ₆ cycloalkyl C ₂ to C ₆ alkenyl, C ₂ to C ₆ alkynyl, C ₃ to C ₆ cycloalkyl C ₂ to C ₆ alkynyl, C ₁ to C ₆ haloalkane Group, C ₃ to C ₆ halocycloalkyl, C ₃ to C ₆ halocycloalkyl C ₁ to C ₆ alkyl, C ₂ to C ₆ haloalkenyl, C ₂ to C ₆ haloalkynyl, hydroxyl, amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkylcarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ haloalkylcarbonyl) amine C ₁ to C ₆ alkyl Group, mono (C ₃ to C ₆ cycloalkylcarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkoxycarbonyl) amine C ₁ to C ₆ alkyl, mono (C ₁ To C ₆ alkyl)aminocarbonylamino C ₁ to C ₆ alkyl, di(C ₁ to C ₆ alkyl)aminocarbonylamino C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ alkyl) Sulfosulfonyl)amino C ₁ to C ₆ alkyl, mono(C ₁ to C ₆ haloalkylsulfonyl) amino C ₁ to C ₆ alkyl, N-(C ₁ to C ₆ alkylsulfonate Acyl)-N-(C ₁ to C ₆ alkyl)amine C ₁ to C ₆ alkyl, N-(C ₁ to C ₆ haloalkylsulfonyl)-N-(C ₁ to C ₆ alkyl Group) amine group C ₁ to C ₆ alkyl, hydroxy C ₁ to C ₆ alkyl, C ₁ to C ₆ alkoxy C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkoxy C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkoxy C ₁ to C ₆ haloalkyl, C ₃ to C ₆ cycloalkoxy C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkoxy C ₁ to C ₆ alkyl groups, unsubstituted or mono- or poly-substituted phenyl substituted by substituent group α, unsubstituted or mono- or poly-substituted substituents selected by substituent group α Heteroaryl, unsubstituted or substituted by substituent group α mono- or polysubstituted phenyl C ₁ to C ₃ alkyl, unsubstituted or substituted by substituent group α mono-substituted Or polysubstituted phenyl C ₁ to C ₃ haloalkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroaryl C ₁ to C ₃ alkyl, unsubstituted or The substituents selected through the substituent group α are mono- or polysubstituted heteroaryl C ₁ to C ₃ haloalkyl, cyano C ₁ to C ₆ alkyl, unsubstituted or selected through the substituent group α Substituted mono- or poly-substituted phenoxy C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or poly-substituted heteroaryloxy C ₁ to C ₃ alkyl Phenyl, unsubstituted or selected via substituent group α, mono- or polysubstituted phenyl C ₁ to C 3 alkoxy C ₁ to C 3 alkyl, unsubstituted or selected via substituent group α Substituent Mono- or poly-substituted heteroaryl C ₁ to C 3 alkoxy C ₁ to C 3 alkyl, mercapto C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylthio C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfinyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylthio C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylsulfinyl C ₁ to C ₆ alkyl, C ₁ to C ₆ haloalkylsulfonyl C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkane Alkylthio C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkylsulfinyl C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkylsulfonyl C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylthio C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylsulfinyl C ₁ to C ₆ alkyl, C ₃ to C ₆ halocycloalkylsulfonate Acyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylsulfonyloxy C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylcarbonylthio C ₁ to C ₃ alkyl, unsubstituted Phenylthio C ₁ to C3 alkyl substituted by the substituent selected by the substituent group α, unsubstituted or substituted by the substituent selected by the substituent group α Sulfenyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or poly-substituted phenylsulfonyl C ₁ to C ₃ alkyl, unsubstituted or Heteroarylthio C ₁ to C3 alkyl substituted by substituents selected through substituent group α, unsubstituted or substituted monosubstituted or polysubstituted heteroaromatic groups selected through substituent group α Sulfonyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroarylsulfonyl C ₁ to C ₃ alkyl, unsubstituted Or mono- or poly-substituted phenyl C ₁ to C ₃ alkylthio C ₁ to C ₃ alkyl, unsubstituted or selected by substituent group α Substituted or polysubstituted phenyl C ₁ to C ₃ alkylsulfinyl C ₁ to C ₃ alkyl, unsubstituted or substituted by substituent group α, mono- or poly-substituted phenyl C ₁ To C ₃ alkylsulfonyl C ₁ to C ₃ alkyl, unsubstituted or substituted via substituent group α, mono- or multi-substituted heteroaryl C ₁ to C ₃ alkylthio C ₁ To C3 alkyl, unsubstituted or substituted via substituent group α, mono- or polysubstituted heteroaryl C ₁ to C ₃ alkylsulfinyl C ₁ to C ₃ alkyl, unsubstituted Or a mono- or poly-substituted heteroaryl C ₁ to C ₃ alkylsulfonyl C ₁ to C ₃ alkyl, heterocycloalkyl C ₁ to C ₆ alkyl selected from the substituents selected through the substituent group α, C ₁ to C ₆ alkylcarbonyl C ₁ to C ₆ alkyl, unsubstituted or substituted by a substituent group α, mono- or polysubstituted phenylcarbonyl C ₁ to C ₃ alkyl, Heteroarylcarbonyl C ₁ to C ₃ alkyl, hydroxycarbonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkoxy, unsubstituted or selected via substituent group α Carbonyl C ₁ to C ₃ alkyl, mono (C ₁ to C ₆ alkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₁ to C ₆ haloalkyl) aminocarbonyl C ₁ to C ₆ alkyl Group, mono (C ₃ to C ₆ cycloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, mono (C ₃ to C ₆ halocycloalkyl) aminocarbonyl C ₁ to C ₆ alkyl, di (C ₁ to C ₆ alkyl) aminocarbonyl C ₁ to C ₆ alkyl, C ₁ to C ₆ alkylcarbonyloxy C ₁ to C ₃ alkyl, C ₁ to C ₆ haloalkylcarbonyloxy C ₁ to C ₃ alkyl, nitro, amine, carboxamide, C ₁ to C ₆ alkylcarbonyl, carboxy, C ₁ to C ₆ alkoxycarbonyl, amine carboxamide, mono (C ₁ to C ₆ alkyl )Aminocarbonyl, mono(C ₁ to C ₆ haloalkyl)aminocarbonyl, di(C ₁ to C ₆ alkyl)aminocarbonyl, di(C ₁ to C ₆ haloalkyl)aminocarbonyl, or (1,3-bi- pendant isoindoline-2-yl) C ₁ to C ₃ alkyl, and R ⁵ and R ⁷ can also form 3 to 3 together with the nitrogen atoms to which they are bonded 6-membered heterocyclic ring, or 3 to 6-membered heterocyclic ring having 1 to 4 heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom, R ⁶ represents a hydrogen atom or a C ₁ to C ₆ alkyl group, R ⁷ represents a hydrogen atom, C ₁ to C ₆ alkyl, C ₃ to C ₆ cycloalkyl, C ₃ to C ₆ cycloalkyl C ₁ to C ₆ alkyl, C ₂ to C ₆ alkenyl, C ₂ to C ₆ alkynyl, methyl acetyl, C ₁ to C ₆ alkylcarbonyl, C ₁ to C ₆ alkoxycarbonyl, C ₁ to C ₆ alkylsulfonyl or C ₁ to C ₆ haloalkylsulfonyl , R ⁹ represents a hydrogen atom, a halogen atom or a cyano group, Substituent group α represents a halogen atom, C ₁ to C ₆ alkyl group, C ₁ to C ₆ haloalkyl group, hydroxyl group, C ₁ to C ₆ alkoxy group, C ₁ to C ₆ haloalkoxy group, nitro group, Cyano, mercapto, C ₁ to C ₆ alkylthio, C ₁ to C ₆ haloalkylthio, C ₁ to C ₆ alkylsulfinyl, C ₁ to C ₆ haloalkylsulfinyl , C ₁ to C ₆ alkylsulfonyl, C ₁ to C ₆ haloalkylsulfonyl, amine, mono (C ₁ to C ₆ alkyl) amine, di (C ₁ to C ₆ alkyl) Amino, mono (C ₁ to C ₆ alkylsulfonyl) amine, mono (C ₁ to C ₆ haloalkylsulfonyl) amine, N-(C ₁ to C ₆ alkylsulfonyl) -N-(C ₁ to C ₆ alkyl)amino, N-(C ₁ to C ₆ haloalkylsulfonyl)-N-(C ₁ to C ₆ alkyl)amino, carboxamide, carboxyl , C ₁ to C ₆ alkylcarbonyl, C ₁ to C ₆ alkoxycarbonyl.