Pyrazole-3-carboxylic acid amide derivative and pest control agent

文档序号：1651915 发布日期：2019-12-24 浏览：17次中文

阅读说明：本技术 吡唑-3-羧酸酰胺衍生物及有害生物防治剂 (Pyrazole-3-carboxylic acid amide derivative and pest control agent ) 是由金原明石川谅鸟谷部启二加藤克也中谷昌央高根泽阳松田武于 2018-05-09 设计创作，主要内容包括：本发明提供具有优异的有害生物防治效果的吡唑-3-羧酸酰胺衍生物或其盐类、以及含有它们作为有效成分的有害生物防治剂。由通式[I]表示的吡唑-3-羧酸酰胺衍生物或其农业上可用的盐类、以及含有它们作为有效成分的有害生物防治剂,<Image he="484" wi="700" file="DDA0002267959280000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>[式中,R1、R2、R3、R4及R5表示氢原子、卤素原子、C1～C6烷基等；R6表示C1～C12烷基、C1～C12卤代烷基等；R7及R8表示氢原子、C1～C12烷基等。]。(The invention provides a pyrazole-3-carboxylic acid amide derivative or a salt thereof having an excellent pest control effect,And a pest control agent containing them as an active ingredient. Is represented by the general formula [ I]The pyrazole-3-carboxylic acid amide derivative represented by the formula (I) or an agriculturally acceptable salt thereof, and a pest control agent containing the same as an active ingredient, [ in the formula, R 1 、R 2 、R 3 、R 4 And R 5 Represents a hydrogen atom, a halogen atom, C 1 ～C 6 Alkyl, etc.; r 6 Is represented by C 1 ～C 12 Alkyl radical, C 1 ～C 12 Haloalkyl, etc.; r 7 And R 8 Represents a hydrogen atom, C 1 ～C 12 Alkyl groups, and the like.]。)

1. Pyrazole-3-carboxylic acid amide derivatives represented by the general formula [1], or agriculturally useful salts thereof,

[ chemical formula 1]

[ in the formula,

n represents an integer of 0 or 1;

x represents an oxygen atom or a sulfur atom;

R¹、R²、R³、R⁴and R⁵Each independently represents a hydrogen atom, a halogen atom, C₁～C₆Alkyl radical, C₁～C₆Haloalkyl, C₁～C₆Alkoxy radical, C₁～C₆Haloalkoxy, C₃～C₆Cycloalkyl radical, C₁～C₆Alkylthio radical, C₁～C₆Alkylsulfinyl radical, C₁～C₆Alkylsulfonyl, amino, mono (C)₁～C₆Alkyl) amino, di (C)₁～C₆Alkyl) amino, cyano or nitro;

R⁶represents a hydrogen atom, C₁～C₁₂Alkyl radical, C₁～C₆Alkoxy radical C₁～C₆Alkyl radical, C₁～C₁₂Haloalkyl, C₁～C₆Alkoxy radical C₁～C₆Haloalkyl, C₁～C₆Halogenoalkoxy radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxy radical C₁～C₆Haloalkyl, C₂～C₇Alkynyl, C₃～C₆Cycloalkyl radical C₂～C₆Alkynyl, C₂～C₆Halogenated alkynyl, C₂～C₆Alkenyl radical, C₂～C₆Haloalkenyl, C₃～C₆Cycloalkyl radical, C₃～C₆Halogenocycloalkyl, C₁～C₆Haloalkyl C₃～C₆Cycloalkyl radical, C₃～C₆Cycloalkyl radical C₁～C₆Alkyl radical, C₃～C₆Halogenocycloalkyl C₁～C₆Alkyl radical, C₁～C₆Alkylthio group C₁～C₆Alkyl radical, C₁～C₆Alkylsulfinyl radical C₁～C₆Alkyl radical, C₁～C₆Alkylsulfonyl radical C₁～C₆Alkyl radical, C₁～C₆Haloalkylthio C₁～C₆Alkyl, aryl, heteroaryl, and heteroaryl,C₁～C₆Halogenoalkylsulfinyl C₁～C₆Alkyl radical, C₁～C₆Haloalkylsulfonyl C₁～C₆Alkyl radical, C₁～C₆Alkyl carbonyl radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkylcarbonyl group C₁～C₆Alkyl radical, C₁～C₆Alkoxycarbonyl radical C₁～C₆Alkyl, aminocarbonyl C₁～C₆Alkyl, mono (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₃～C₆Cycloalkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Haloalkyl) aminocarbonyl C₁～C₆Alkyl, di (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Alkylcarbonyl) amino C₁～C₆Alkyl, mono (C)₁～C₆Alkoxycarbonyl) amino group C₁～C₆Alkyl, mono (C)₁～C₆Alkylsulfonyl) amino C₁～C₆Alkyl, mono (C)₁～C₆Haloalkylsulfonyl) amino C₁～C₆Alkyl, hydroxy C₁～C₆Alkyl, hydroxyimino C₁～C₆Alkyl radical, C₁～C₆Alkoxyimino radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxyimino radical C₁～C₆Alkyl, or unsubstituted or substituted by R⁹Substituted C₇～C₁₃Aralkyl group;

R⁷and R⁸Each independently represents a hydrogen atom, C₁～C₆Alkyl radical, C₃～C₆Cycloalkyl radical, C₃～C₆Cycloalkyl radical C₁～C₆Alkyl radical, C₂～C₇Alkynyl, C₂～C₆Alkenyl, hydroxy, C₁～C₆Alkoxy radical, C₁～C₆Alkoxy radical C₁～C₆Alkyl radical, C₁～C₆Haloalkyl, 2-tetrahydrofuryl, 3-tetrahydrofuryl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, cyano C₁～C₆Alkyl, cyano C₃～C₆Cycloalkyl, hydroxy C₁～C₆Alkyl, formyl, amino, mono (C)₁～C₆Alkyl) amino, di (C)₁～C₆Alkyl) amino, C₁～C₆Alkylcarbonyl group, C₁～C₆Alkoxy radical C₁～C₆Alkylcarbonyl group, C₃～C₆Cycloalkyl carbonyl group, C₃～C₆Cycloalkyl radical C₁～C₆Alkylcarbonyl group, C₁～C₆Alkoxycarbonyl, carbamoyl, mono (C)₁～C₆Alkyl) aminocarbonyl, di (C)₁～C₆Alkyl) aminocarbonyl, unsubstituted or substituted by R⁹Substituted phenylcarbonyl, unsubstituted or substituted by R⁹Substituted C₇～C₁₃Aralkylcarbonyl, unsubstituted or substituted by R⁹Substituted pyridylcarbonyl, unsubstituted or substituted by R⁹Substituted pyrazolyl carbonyl, (C)₁～C₆Alkyl) thiocarbonyl, (C)₁～C₆Alkoxy) thiocarbonyl, thiocarbamoyl, mono (C)₁～C₆Alkyl) aminothiocarbonyl, di (C)₁～C₆Alkyl) aminothiocarbonyl, C₁～C₆Alkylsulfonyl, aminosulfonyl, mono (C)₁～C₆Alkyl) aminosulfonyl, di (C)₁～C₆Alkyl) aminosulfonyl, R¹⁰R¹¹N-C₁～C₆Alkyl radical, C₁～C₆Alkoxycarbonyl radical C₁～C₆Alkyl, aminocarbonyl C₁～C₆Alkyl, mono (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₃～C₆Cycloalkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Haloalkyl) aminocarbonyl C₁～C₆Alkyl, di (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl radicalHydroxyimino group, C₁～C₆Alkoxyimino group, hydroxyimino group C₁～C₆Alkyl radical, C₁～C₆Alkoxyimino radical C₁～C₆An alkyl group; in addition, R⁷And R⁸Or may be formed together as ═ CR¹²N(R¹³)R¹⁴Or ═ CR¹²OR¹⁵(ii) a Furthermore, R⁷And R⁸Or may form a 3-to 6-membered carbocyclic ring together with the carbon atom to which they are bonded, or a 3-to 6-membered heterocyclic ring having 1 to 4 hetero atoms selected from an oxygen atom, a sulfur atom and a nitrogen atom, wherein the heterocyclic ring may be substituted with a halogen atom, a cyano group, a nitro group, or C₁～C₆Alkyl radical, C₁～C₆Alkoxy radical, C₁～C₆Haloalkyl or oxo;

R⁹represents a halogen atom, C₁～C₆Alkyl radical, C₁～C₆Haloalkyl, C₁～C₆Alkoxy radical, C₁～C₆Haloalkoxy, C₁～C₆Alkylthio radical, C₁～C₆Alkylsulfinyl radical, C₁～C₆Alkylsulfonyl radical, C₁～C₆Haloalkylthio, C₁～C₆Haloalkylsulfinyl radical, C₁～C₆Haloalkylsulfonyl, amino, mono (C)₁～C₆Alkyl) amino, di (C)₁～C₆Alkyl) amino, cyano or nitro;

R¹⁰and R¹¹Each independently represents a hydrogen atom, C₁～C₆Alkyl radical, C₁～C₆Haloalkyl or C₃～C₆Cycloalkyl, furthermore, R¹⁰And R¹¹Or may form a 3-6 membered ring together with the carbon atom to which they are bonded;

R¹²represents a hydrogen atom, C₁～C₆Alkyl radical, C₃～C₆A cycloalkyl group;

R¹³and R¹⁴Each independently represents a hydrogen atom, C₁～C₆Alkyl radical, C₁～C₆Haloalkyl, C₃～C₆Cycloalkyl radical, C₁～C₆Alkoxy radical, in addition, R¹³And R¹⁴Or may form a 3-to 6-membered carbocyclic ring together with the carbon atoms to which they are bonded, or a 3-to 6-membered heterocyclic ring having 1 to 4 hetero atoms selected from an oxygen atom, a sulfur atom and a nitrogen atom;

R¹⁵is represented by C₁～C₆An alkyl group.]。

2. Pyrazole-3-carboxylic acid derivatives represented by the general formula [ II ], or salts thereof,

[ chemical formula 2]

[ in the formula,

n represents an integer of 0 or 1;

R⁶represents a hydrogen atom, C₁～C₁₂Alkyl radical, C₁～C₆Alkoxy radical C₁～C₆Alkyl radical, C₁～C₁₂Haloalkyl, C₁～C₆Alkoxy radical C₁～C₆Haloalkyl, C₁～C₆Halogenoalkoxy radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxy radical C₁～C₆Haloalkyl, C₂～C₇Alkynyl, C₃～C₆Cycloalkyl radical C₂～C₆Alkynyl, C₂～C₆Halogenated alkynyl, C₂～C₆Alkenyl radical, C₂～C₆Haloalkenyl, C₃～C₆Cycloalkyl radical, C₃～C₆Halogenocycloalkyl, C₁～C₆Haloalkyl C₃～C₆Cycloalkyl radical, C₃～C₆Cycloalkyl radical C₁～C₆Alkyl radical, C₃～C₆Halogenocycloalkyl C₁～C₆Alkyl radical, C₁～C₆Alkylthio group C₁～C₆Alkyl radical, C₁～C₆Alkylsulfinyl radical C₁～C₆Alkyl radical, C₁～C₆Alkylsulfonyl radical C₁～C₆Alkyl radical, C₁～C₆Haloalkylthio C₁～C₆Alkyl radical, C₁～C₆Halogenoalkylsulfinyl C₁～C₆Alkyl radical, C₁～C₆Haloalkylsulfonyl C₁～C₆Alkyl radical, C₁～C₆Alkyl carbonyl radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkylcarbonyl group C₁～C₆Alkyl radical, C₁～C₆Alkoxycarbonyl radical C₁～C₆Alkyl, aminocarbonyl C₁～C₆Alkyl, mono (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₃～C₆Cycloalkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Haloalkyl) aminocarbonyl C₁～C₆Alkyl, di (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Alkylcarbonyl) amino C₁～C₆Alkyl, mono (C)₁～C₆Alkoxycarbonyl) amino group C₁～C₆Alkyl, mono (C)₁～C₆Alkylsulfonyl) amino C₁～C₆Alkyl, mono (C)₁～C₆Haloalkylsulfonyl) amino C₁～C₆Alkyl, hydroxy C₁～C₆Alkyl, hydroxyimino C₁～C₆Alkyl radical, C₁～C₆Alkoxyimino radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxyimino radical C₁～C₆Alkyl, unsubstituted or substituted by R⁹Substituted C₇～C₁₃Aralkyl group;

R¹⁶represents a hydrogen atom or C₁～C₆An alkyl group.]。

3. Pyrazole-3-carboxylic acid amide derivatives according to claim 1, or agriculturally useful salts thereof,

R⁶is represented by C₁～C₁₂Alkyl radical, C₁～C₆Alkoxy radical C₁～C₆Alkyl radical, C₁～C₁₂Haloalkyl, C₁～C₆Alkoxy radical C₁～C₆Haloalkyl, C₁～C₆Halogenoalkoxy radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxy radical C₁～C₆Haloalkyl, C₂～C₇Alkynyl, C₃～C₆Cycloalkyl radical C₂～C₆Alkynyl, C₂～C₆Halogenated alkynyl, C₂～C₆Alkenyl radical, C₂～C₆Haloalkenyl, C₃～C₆Cycloalkyl radical, C₃～C₆Halogenocycloalkyl, C₁～C₆Haloalkyl C₃～C₆Cycloalkyl radical, C₃～C₆Cycloalkyl radical C₁～C₆Alkyl radical, C₃～C₆Halogenocycloalkyl C₁～C₆Alkyl radical, C₁～C₆Alkylthio group C₁～C₆Alkyl radical, C₁～C₆Alkylsulfinyl radical C₁～C₆Alkyl radical, C₁～C₆Alkylsulfonyl radical C₁～C₆Alkyl radical, C₁～C₆Haloalkylthio C₁～C₆Alkyl radical, C₁～C₆Halogenoalkylsulfinyl C₁～C₆Alkyl radical, C₁～C₆Haloalkylsulfonyl C₁～C₆Alkyl radical, C₁～C₆Alkyl carbonyl radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkylcarbonyl group C₁～C₆Alkyl radical, C₁～C₆Alkoxycarbonyl radical C₁～C₆Alkyl, aminocarbonyl C₁～C₆Alkyl, mono (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₃～C₆Cycloalkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Haloalkyl) aminocarbonyl C₁～C₆Alkyl, di (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Alkylcarbonyl) amino C₁～C₆Alkyl, mono (C)₁～C₆Alkoxycarbonyl) amino group C₁～C₆Alkyl, mono (C)₁～C₆Alkylsulfonyl) amino C₁～C₆Alkyl, mono (C)₁～C₆Haloalkylsulfonyl) amino C₁～C₆Alkyl, hydroxy C₁～C₆Alkyl, hydroxyimino C₁～C₆Alkyl radical, C₁～C₆Alkoxyimino radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxyimino radical C₁～C₆Alkyl, or unsubstituted or substituted by R⁹Substituted C₇～C₁₃An aralkyl group.

4. The pyrazole-3-carboxylic acid derivative according to claim 2, or a salt thereof,

R⁶is represented by C₁～C₁₂Alkyl radical, C₁～C₆Alkoxy radical C₁～C₆Alkyl radical, C₁～C₁₂Haloalkyl, C₁～C₆Alkoxy radical C₁～C₆Haloalkyl, C₁～C₆HaloalkoxyRadical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxy radical C₁～C₆Haloalkyl, C₂～C₇Alkynyl, C₃～C₆Cycloalkyl radical C₂～C₆Alkynyl, C₂～C₆Halogenated alkynyl, C₂～C₆Alkenyl radical, C₂～C₆Haloalkenyl, C₃～C₆Cycloalkyl radical, C₃～C₆Halogenocycloalkyl, C₁～C₆Haloalkyl C₃～C₆Cycloalkyl radical, C₃～C₆Cycloalkyl radical C₁～C₆Alkyl radical, C₃～C₆Halogenocycloalkyl C₁～C₆Alkyl radical, C₁～C₆Alkylthio group C₁～C₆Alkyl radical, C₁～C₆Alkylsulfinyl radical C₁～C₆Alkyl radical, C₁～C₆Alkylsulfonyl radical C₁～C₆Alkyl radical, C₁～C₆Haloalkylthio C₁～C₆Alkyl radical, C₁～C₆Halogenoalkylsulfinyl C₁～C₆Alkyl radical, C₁～C₆Haloalkylsulfonyl C₁～C₆Alkyl radical, C₁～C₆Alkyl carbonyl radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkylcarbonyl group C₁～C₆Alkyl radical, C₁～C₆Alkoxycarbonyl radical C₁～C₆Alkyl, aminocarbonyl C₁～C₆Alkyl, mono (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₃～C₆Cycloalkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Haloalkyl) aminocarbonyl C₁～C₆Alkyl, di (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Alkylcarbonyl) amino C₁～C₆Alkyl, mono (C)₁～C₆Alkoxycarbonyl) amino group C₁～C₆Alkyl, aryl, heteroaryl, and heteroaryl,Mono (C)₁～C₆Alkylsulfonyl) amino C₁～C₆Alkyl, mono (C)₁～C₆Haloalkylsulfonyl) amino C₁～C₆Alkyl, hydroxy C₁～C₆Alkyl, hydroxyimino C₁～C₆Alkyl radical, C₁～C₆Alkoxyimino radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxyimino radical C₁～C₆Alkyl, or unsubstituted or substituted by R⁹Substituted C₇～C₁₃An aralkyl group.

5. A pesticidal composition comprising the pyrazole-3-carboxylic acid amide derivative according to claim 1 or 3 or an agriculturally acceptable salt thereof, or the pyrazole-3-carboxylic acid derivative according to claim 2 or 4 or an agriculturally acceptable salt thereof as an active ingredient.

6. The pesticidal composition according to claim 5, wherein the pesticidal composition further contains a surfactant.

7. A pest control agent comprising the pyrazole-3-carboxylic acid amide derivative according to claim 1 or 3 or an agriculturally acceptable salt thereof, or the pyrazole-3-carboxylic acid derivative according to claim 2 or 4 or an agriculturally acceptable salt thereof as an active ingredient.

8. A pest control agent according to claim 7, which is an insecticide.

9. The pest control agent according to claim 7, which has a controlling effect on pests in dry or paddy fields where plants for agricultural and horticultural use are cultivated.

10. The pest control agent according to claim 9, wherein the plant for agricultural and horticultural use is a plant to which tolerance has been imparted by breeding or genetic recombination technology.

11. A method for controlling harmful organisms, which comprises using as an active ingredient an amount of the pyrazole-3-carboxylic acid amide derivative according to claim 1 or 3 or an agriculturally acceptable salt thereof, or the pyrazole-3-carboxylic acid derivative according to claim 2 or 4 or an agriculturally acceptable salt thereof.

12. A method for controlling pests, which comprises applying a pesticidal composition comprising the pyrazole-3-carboxylic acid amide derivative according to claim 1 or 3 or an agriculturally acceptable salt thereof or the pyrazole-3-carboxylic acid derivative according to claim 2 or 4 or an agriculturally acceptable salt thereof as an active ingredient to agricultural or horticultural crops or to a locus where agricultural or horticultural crops are to be grown or are being grown, simultaneously or separately.

13. A method of controlling pests according to claim 11 or 12, wherein the place to which the pest control agent is applied is paddy field, dry land, grassland, orchard, non-agricultural land, greenhouse, nursery, plant factory.

14. The method for controlling pests according to any one of claims 11 to 13, wherein a pyrazole-3-carboxylic acid amide derivative or an agriculturally acceptable salt thereof is used as the pesticide.

15. A method of using a pest control agent, wherein the pest control agent of any one of claims 7 to 10 is used for controlling organisms harmful to crops for agricultural and horticultural use.

Technical Field

The present invention relates to a novel pyrazole-3-carboxylic acid amide derivative or an agriculturally acceptable salt thereof, and a pest control agent containing the derivative as an active ingredient.

Background

Patent document 1 describes pyrazole-3-carboxylic acid amide derivatives having pest control effects, but the compounds described in patent document 1 are limited to oxazepine (oxazepine) derivatives in which a benzene ring substituted on the nitrogen atom of the carboxamide group at the 3-position of the pyrazole ring forms a ring with the hydroxyl group at the 4-position.

Patent documents 2 and 3 describe pyrazole-3-carboxylic acid amide derivatives having anticancer activity, but the compounds described in patent documents 2 and 3 are limited to those in which a benzene ring and a pyridine ring are substituted on the nitrogen atom of the carboxylic acid amide at the 3-position of the pyrazole ring.

Disclosure of Invention

Problems to be solved by the invention

However, in patent document 1, there is no description about a pyrazole-3-carboxylic acid amide derivative having a (substituted) alkoxy group at the 4-position of the pyrazole ring. On the other hand, in patent documents 2 and 3, there is no description about a pyrazole-3-carboxylic acid amide derivative having an unsubstituted or (substituted) alkyl group on the nitrogen atom at the carboxylic acid amide position at the 3-position of the pyrazole ring. A pest control agent for useful crops is desirably an agent which is applied to soil or foliage and exhibits a sufficient pest control effect at a low dose. Further, there are increasing demands for safety of chemical substances and environmental impact, and development of safer pest control agents is desired. In addition, in recent years, pests resistant to pest control agents such as insecticides and acaricides have appeared due to long-term use of the pest control agents, and it has been difficult to completely control pests. Further, the use of pest control agents having high toxicity to humans and animals also poses problems in terms of safety of operators and the like.

Under such circumstances, an object of the present invention is to solve the above-mentioned problems of conventional pest control agents and to provide a pest control agent having excellent safety, control effect, residual efficacy, and the like.

Means for solving the problems

In order to develop a pest control agent having the above-described preferable characteristics, the present inventors synthesized various pyrazole-3-carboxylic acid amide derivatives and conducted intensive studies with respect to their physiological activities. As a result, they have found that pyrazole-3-carboxylic acid amide derivatives represented by the following general formula [ I ] (hereinafter referred to as compounds of the present invention) exhibit excellent effects on various pests, and have continued research to complete the present invention.

That is, the gist of the present invention is to have the following characteristics.

(1) A pyrazole-3-carboxylic acid amide derivative represented by the general formula [1 ]:

[ chemical formula 1]

[ in the formula,

n represents an integer of 0 or 1;

x represents an oxygen atom or a sulfur atom;

R⁶represents a hydrogen atom, C₁～C₁₂Alkyl radical, C₁～C₆Alkoxy radical C₁～C₆Alkyl radical, C₁～C₁₂Haloalkyl, C₁～C₆Alkoxy radical C₁～C₆Haloalkyl, C₁～C₆Halogenoalkoxy radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxy radical C₁～C₆Haloalkyl, C₂～C₇Alkynyl, C₃～C₆Cycloalkyl radical C₂～C₆Alkynyl, C₂～C₆Halogenated alkynyl, C₂～C₆Alkenyl radical, C₂～C₆Haloalkenyl, C₃～C₆Cycloalkyl radical, C₃～C₆Halogenocycloalkyl, C₁～C₆Haloalkyl C₃～C₆Cycloalkyl radical, C₃～C₆Cycloalkyl radical C₁～C₆Alkyl radical, C₃～C₆Halogenocycloalkyl C₁～C₆Alkyl radical, C₁～C₆Alkylthio group C₁～C₆Alkyl radical, C₁～C₆Alkylsulfinyl radical C₁～C₆Alkyl radical, C₁～C₆Alkylsulfonyl radical C₁～C₆Alkyl radical, C₁～C₆Haloalkylthio C₁～C₆Alkyl radical, C₁～C₆Halogenoalkylsulfinyl C₁～C₆Alkyl radical, C₁～C₆Haloalkylsulfonyl C₁～C₆Alkyl radical, C₁～C₆Alkyl carbonyl radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkylcarbonyl group C₁～C₆Alkyl radical, C₁～C₆Alkoxycarbonyl radical C₁～C₆Alkyl, aminocarbonyl C₁～C₆Alkyl, mono (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₃～C₆Cycloalkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Haloalkyl) aminocarbonyl C₁～C₆Alkyl, di (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Alkylcarbonyl) amino C₁～C₆Alkyl, mono (C)₁～C₆Alkoxycarbonyl) amino group C₁～C₆Alkyl, mono (C)₁～C₆Alkyl) sulfonylamino C₁～C₆Alkyl, mono (C)₁～C₆Haloalkylsulfonyl) amino C₁～C₆Alkyl, aryl, heteroaryl, and heteroaryl,Hydroxy radical C₁～C₆Alkyl, hydroxyimino C₁～C₆Alkyl radical, C₁～C₆Alkoxyimino radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxyimino radical C₁～C₆Alkyl, or unsubstituted or substituted by R⁹Substituted C₇～C₁₃Aralkyl group;

R⁷and R⁸Each independently represents a hydrogen atom, C₁～C₆Alkyl radical, C₃～C₆Cycloalkyl radical, C₃～C₆Cycloalkyl radical C₁～C₆Alkyl radical, C₂～C₇Alkynyl, C₂～C₆Alkenyl, hydroxy, C₁～C₆Alkoxy radical, C₁～C₆Alkoxy radical C₁～C₆Alkyl radical, C₁～C₆Haloalkyl, 2-tetrahydrofuryl, 3-tetrahydrofuryl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, cyano C₁～C₆Alkyl, cyano C₃～C₆Cycloalkyl, hydroxy C₁～C₆Alkyl, formyl, amino, mono (C)₁～C₆Alkyl) amino, di (C)₁～C₆Alkyl) amino, C₁～C₆Alkylcarbonyl group, C₁～C₆Alkoxy radical C₁～C₆Alkylcarbonyl group, C₃～C₆Cycloalkyl carbonyl group, C₃～C₆Cycloalkyl radical C₁～C₆Alkylcarbonyl group, C₁～C₆Alkoxycarbonyl, carbamoyl, mono (C)₁～C₆Alkyl) aminocarbonyl, di (C)₁～C₆Alkyl) aminocarbonyl, unsubstituted or substituted by R⁹Substituted phenylcarbonyl, unsubstituted or substituted by R⁹Substituted C₇～C₁₃Aralkylcarbonyl, unsubstituted or substituted by R⁹Substituted pyridylcarbonyl, unsubstituted or substituted by R⁹Substituted pyrazolyl carbonyl, (C)₁～C₆Alkyl) thiocarbonyl, (C)₁～C₆Alkoxy) thiocarbonyl, thiocarbamoyl, mono (C)₁～C₆Alkyl) aminothiocarbonylBase, di (C)₁～C₆Alkyl) aminothiocarbonyl, C₁～C₆Alkylsulfonyl, aminosulfonyl, mono (C)₁～C₆Alkyl) aminosulfonyl, di (C)₁～C₆Alkyl) aminosulfonyl, R¹⁰R¹¹N-C₁～C₆Alkyl radical, C₁～C₆Alkoxycarbonyl radical C₁～C₆Alkyl, aminocarbonyl C₁～C₆Alkyl, mono (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₃～C₆Cycloalkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Haloalkyl) aminocarbonyl C₁～C₆Alkyl, di (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, hydroxyimino, C₁～C₆Alkoxyimino group, hydroxyimino group C₁～C₆Alkyl radical, C₁～C₆Alkoxyimino radical C₁～C₆An alkyl group; in addition, R⁷And R⁸Or together form ═ CR¹²N(R¹³)R¹⁴Or ═ CR¹²OR¹⁵(ii) a Furthermore, R⁷And R⁸Or may form a 3-to 6-membered carbocyclic ring together with the carbon atom to which they are bonded, or a 3-to 6-membered heterocyclic ring having 1 to 4 hetero atoms selected from an oxygen atom, a sulfur atom and a nitrogen atom, wherein the heterocyclic ring may be substituted with a halogen atom, a cyano group, a nitro group, or C₁～C₆Alkyl radical, C₁～C₆Alkoxy radical, C₁～C₆Haloalkyl or oxo;

R¹²represents a hydrogen atom, C₁～C₆Alkyl radical, C₃～C₆A cycloalkyl group;

R¹³and R¹⁴Each independently represents a hydrogen atom, C₁～C₆Alkyl radical, C₁～C₆Haloalkyl, C₃～C₆Cycloalkyl radical, C₁～C₆Alkoxy radical, in addition, R¹³And R¹⁴Or may form a 3-to 6-membered carbocyclic ring or a 3-to 6-membered heterocyclic ring having 1 to 4 hetero atoms selected from an oxygen atom, a sulfur atom and a nitrogen atom together with the carbon atom to which they are bonded;

R¹⁵is represented by C₁～C₆An alkyl group.]。

(2) A pyrazole-3-carboxylic acid derivative represented by the general formula [ II ]:

[ chemical formula 2]

[ in the formula,

n represents an integer of 0 or 1;

R¹、R²、R³、R⁴and R⁵Each independently represents a hydrogen atom, a halogen atom, C₁～C₆Alkyl radical, C₁～C₆Haloalkyl, C₁～C₆Alkoxy radical, C₁～C₆Haloalkoxy, C₃～C₆Cycloalkyl radical, C₁～C₆Alkylthio, alkylthio,C₁～C₆Alkylsulfinyl radical, C₁～C₆Alkylsulfonyl, amino, mono (C)₁～C₆Alkyl) amino, di (C)₁～C₆Alkyl) amino, cyano or nitro;

R⁶represents a hydrogen atom, C₁～C₁₂Alkyl radical, C₁～C₆Alkoxy radical C₁～C₆Alkyl radical, C₁～C₁₂Haloalkyl, C₁～C₆Alkoxy radical C₁～C₆Haloalkyl, C₁～C₆Halogenoalkoxy radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxy radical C₁～C₆Haloalkyl, C₂～C₇Alkynyl, C₃～C₆Cycloalkyl radical C₂～C₆Alkynyl, C₂～C₆Halogenated alkynyl, C₂～C₆Alkenyl radical, C₂～C₆Haloalkenyl, C₃～C₆Cycloalkyl radical, C₃～C₆Halogenocycloalkyl, C₁～C₆Haloalkyl C₃～C₆Cycloalkyl radical, C₃～C₆Cycloalkyl radical C₁～C₆Alkyl radical, C₃～C₆Halogenocycloalkyl C₁～C₆Alkyl radical, C₁～C₆Alkylthio group C₁～C₆Alkyl radical, C₁～C₆Alkylsulfinyl radical C₁～C₆Alkyl radical, C₁～C₆Alkylsulfonyl radical C₁～C₆Alkyl radical, C₁～C₆Haloalkylthio C₁～C₆Alkyl radical, C₁～C₆Halogenoalkylsulfinyl C₁～C₆Alkyl radical, C₁～C₆Haloalkylsulfonyl C₁～C₆Alkyl radical, C₁～C₆Alkyl carbonyl radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkylcarbonyl group C₁～C₆Alkyl radical, C₁～C₆Alkoxycarbonyl radical C₁～C₆Alkyl, aminocarbonyl C₁～C₆Alkyl, mono (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₃～C₆Cycloalkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Haloalkyl) aminocarbonyl C₁～C₆Alkyl, di (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Alkyl) carbonylamino C₁～C₆Alkyl, mono (C)₁～C₆Alkoxy) carbonylamino C₁～C₆Alkyl, mono (C)₁～C₆Alkylsulfonyl) amino C₁～C₆Alkyl, mono (C)₁～C₆Haloalkylsulfonyl) amino C₁～C₆Alkyl, hydroxy C₁～C₆Alkyl, hydroxyimino C₁～C₆Alkyl radical, C₁～C₆Alkoxyimino radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxyimino radical C₁～C₆Alkyl, unsubstituted or substituted by R⁹Substituted C₇～C₁₃Aralkyl group;

R¹⁶represents a hydrogen atom or C₁～C₆An alkyl group.]。

(3) The pyrazole-3-carboxylic acid amide derivative according to (1) or an agriculturally acceptable salt thereof, wherein R⁶Is represented by C₁～C₁₂Alkyl radical, C₁～C₆Alkoxy radical C₁～C₆Alkyl radical, C₁～C₁₂Haloalkyl, C₁～C₆Alkoxy radical C₁～C₆Haloalkyl, C₁～C₆Halogenoalkoxy radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxy radical C₁～C₆Haloalkyl, C₂～C₇Alkynyl, C₃～C₆Cycloalkyl radical C₂～C₆Alkynyl, C₂～C₆Halogenated alkynyl, C₂～C₆Alkenyl radical, C₂～C₆Haloalkenyl, C₃～C₆Cycloalkyl radical, C₃～C₆Halogenocycloalkyl, C₁～C₆Haloalkyl C₃～C₆Cycloalkyl radical, C₃～C₆Cycloalkyl radical C₁～C₆Alkyl radical, C₃～C₆Halogenocycloalkyl C₁～C₆Alkyl radical, C₁～C₆Alkylthio group C₁～C₆Alkyl radical, C₁～C₆Alkylsulfinyl radical C₁～C₆Alkyl radical, C₁～C₆Alkylsulfonyl radical C₁～C₆Alkyl radical, C₁～C₆Haloalkylthio C₁～C₆Alkyl radical, C₁～C₆Halogenoalkylsulfinyl C₁～C₆Alkyl radical, C₁～C₆Haloalkylsulfonyl C₁～C₆Alkyl radical, C₁～C₆Alkyl carbonyl radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkylcarbonyl group C₁～C₆Alkyl radical, C₁～C₆Alkoxycarbonyl radical C₁～C₆Alkyl, aminocarbonyl C₁～C₆Alkyl, mono (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₃～C₆Cycloalkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Haloalkyl) aminocarbonyl C₁～C₆Alkyl, di (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Alkyl) carbonylamino C₁～C₆Alkyl, mono (C)₁～C₆Alkoxy) carbonylamino C₁～C₆Alkyl, mono (C)₁～C₆Alkyl) sulfonylamino C₁～C₆Alkyl, mono (C)₁～C₆Haloalkyl) sulfonylamino C₁～C₆Alkyl, hydroxy C₁～C₆Alkyl, hydroxyimino C₁～C₆Alkyl radical, C₁～C₆Alkoxyimino radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxyimino radical C₁～C₆Alkyl, unsubstituted or substituted by R⁹Substituted C₇～C₁₃An aralkyl group.

(4) The pyrazole-3-carboxylic acid derivative according to (2) or a salt thereof, wherein R⁶Is represented by C₁～C₁₂Alkyl radical, C₁～C₆Alkoxy radical C₁～C₆Alkyl radical, C₁～C₁₂Haloalkyl, C₁～C₆Alkoxy radical C₁～C₆Haloalkyl, C₁～C₆Halogenoalkoxy radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxy radical C₁～C₆Haloalkyl, C₂～C₇Alkynyl, C₃～C₆Cycloalkyl radical C₂～C₆Alkynyl, C₂～C₆Halogenated alkynyl, C₂～C₆Alkenyl radical, C₂～C₆Haloalkenyl, C₃～C₆Cycloalkyl radical, C₃～C₆Halogenocycloalkyl, C₁～C₆Haloalkyl C₃～C₆Cycloalkyl radical, C₃～C₆Cycloalkyl radical C₁～C₆Alkyl radical, C₃～C₆Halogenocycloalkyl C₁～C₆Alkyl radical, C₁～C₆Alkylthio group C₁～C₆Alkyl radical, C₁～C₆Alkylsulfinyl radical C₁～C₆Alkyl radical, C₁～C₆Alkylsulfonyl radical C₁～C₆Alkyl radical, C₁～C₆Haloalkylthio C₁～C₆Alkyl radical, C₁～C₆Halogenoalkylsulfinyl C₁～C₆Alkyl radical, C₁～C₆Haloalkylsulfonyl C₁～C₆Alkyl radical, C₁～C₆Alkyl carbonyl radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkylcarbonyl group C₁～C₆Alkyl radical, C₁～C₆Alkoxycarbonyl radical C₁～C₆Alkyl, aminocarbonyl C₁～C₆Alkyl, mono (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₃～C₆Cycloalkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Haloalkyl) aminocarbonyl C₁～C₆Alkyl, di (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl, mono (C)₁～C₆Alkyl) carbonylamino C₁～C₆Alkyl, mono (C)₁～C₆Alkoxy) carbonylamino C₁～C₆Alkyl, mono (C)₁～C₆Alkylsulfonyl) amino C₁～C₆Alkyl, mono (C)₁～C₆Haloalkylsulfonyl) amino C₁～C₆Alkyl, hydroxy C₁～C₆Alkyl, hydroxyimino C₁～C₆Alkyl radical, C₁～C₆Alkoxyimino radical C₁～C₆Alkyl radical, C₁～C₆Halogenoalkoxyimino radical C₁～C₆Alkyl, unsubstituted or substituted by R⁹Substituted C₇～C₁₃An aralkyl group.

(5) A pesticidal composition comprising the pyrazole-3-carboxylic acid amide derivative according to (1) or (3) or an agriculturally acceptable salt thereof, or the pyrazole-3-carboxylic acid derivative according to (2) or (4) or an agriculturally acceptable salt thereof as an active ingredient.

(6) The pesticidal composition according to (5), wherein the pesticidal composition further contains a surfactant.

(7) A pest control agent comprising the pyrazole-3-carboxylic acid amide derivative according to (1) or (3) or an agriculturally acceptable salt thereof, or the pyrazole-3-carboxylic acid derivative according to (2) or (4) or an agriculturally acceptable salt thereof as an active ingredient.

(8) The pest control agent according to (7), which is an insecticide.

(9) The pest control agent according to (7), which has a controlling effect on pests in dry or paddy fields in which agricultural or horticultural plants are cultivated.

(10) The pest control agent according to (9), wherein the plant for agricultural or horticultural use is a plant to which tolerance has been imparted by breeding or genetic recombination techniques.

(11) A method for controlling pests, which comprises using as an active ingredient an amount of the pyrazole-3-carboxylic acid amide derivative according to (1) or (3) or an agriculturally acceptable salt thereof, or the pyrazole-3-carboxylic acid derivative according to (2) or (4) or an agriculturally acceptable salt thereof.

(12) A method for controlling pests, which comprises applying a pesticidal composition comprising the pyrazole-3-carboxylic acid amide derivative according to (1) or (3) or an agriculturally acceptable salt thereof or the pyrazole-3-carboxylic acid derivative according to (2) or (4) or an agriculturally acceptable salt thereof as an active ingredient to agricultural or horticultural crops or to a locus where agricultural or horticultural crops are to be grown or are being grown simultaneously or separately.

(13) The method for controlling harmful bio-organisms according to (11) or (12), wherein the site to which the harmful bio-organism controlling agent is applied is paddy field, dry land, grassland, fruit tree garden, non-agricultural land, greenhouse, nursery garden or plant factory.

(14) The method for controlling harmful organisms according to any one of (11) to (13), wherein a pyrazole-3-carboxylic acid amide derivative or an agriculturally acceptable salt thereof is used as the pesticide.

(15) A method for using a pest control agent, wherein the pest control agent of any one of (7) to (10) is used for controlling an organism harmful to an agricultural or horticultural crop.

ADVANTAGEOUS EFFECTS OF INVENTION

The pest control agent containing the compound of the present invention exhibits an excellent control effect on a wide range of pests such as hemipteran pests, lepidopteran pests, coleopteran pests, dipteran pests, hymenopteran pests, orthopteran pests, isopteran pests, thysanopteran pests, acarina pests, plant-parasitic nematodes and the like, and can also control pests having drug resistance to a jig.

Detailed Description

The symbols and terms described in the present specification will be described.

In the present invention, the "pest control agent" refers to an insecticide, acaricide, nematicide, etc. for use in the fields of agriculture and horticulture, animals such as domestic animals and pets, and domestic or epidemic prevention.

In the present invention, "halogen atom" means fluorine atom, chlorine atom, bromine atom, and iodine atom.

In the present invention, "C₁～C₆The symbol "etc. indicates that the number of carbon atoms in the subsequent substituent is 1 to 6 in this case.

In the present invention, "C" is not particularly limited₁～C₆The "alkyl group" represents a linear or branched alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a n-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 1-ethylpropyl group, a 1, 1-dimethylpropyl group, a 1, 2-dimethylpropyl group, a neopentyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 4-methylpentyl group, a 1-ethylbutyl group, a 2-ethylbutyl group, a 1, 1-dimethylbutyl group, a 1, 2-dimethylbutyl group, a 1, 3-dimethylbutyl group, a 2, 2-dimethylbutyl group, a 2,3-, 1,1, 2-trimethylpropyl, 1,2, 2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl.

In the present invention, "C" is not particularly limited₁～C₁₂The alkyl group represents a linear or branched alkyl group having 1 to 12 carbon atoms, except for the above-mentioned "C₁～C₆Examples of the "alkyl group" include, in addition to the examples, groups such as an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, a4, 4-dimethylpentyl group, a 5-methylhexyl group, a 5, 5-dimethylhexyl group, a3, 5, 5-trimethylhexyl group, a 6-methylheptyl group, a 6, 6-dimethylheptyl group, a3, 6, 6-trimethylheptyl group, a 7-methyloctyl group, a 7, 7-dimethyloctyl group, an 8-methylnonyl group, an 8, 8-dimethylnonyl group, a 9-methyldecyl group, a 9, 9-dimethyldecyl group and a 10-methylundecyl group.

In the present invention, unless otherwise specified "C₂～C₆The "alkenyl group" represents a straight-chain or branched alkenyl group having 2 to 6 carbon atoms, and examples thereof include a vinyl group, a 1-propenyl group, an isopropenyl group, a 2-propenyl group, a 1-butenyl group, a 1-methyl-1-propenyl group, a 2-butenyl group, a 1-methyl-2-propenyl group, a 3-butenyl group, a 2-methyl-1-propenyl group, a 2-methyl-2-propenyl group, a 1, 3-butadienyl group, a 1-pentenyl group, a 1-ethyl-2-propenyl group, a 2-pentenyl group, a 1-methyl-1-butenyl group, a 3-pentenyl group, a 1-methyl-2-butenyl group, a 4-pentenyl group, a 1-methyl-3-butenyl group, a 1-methyl-2-butenyl, 3-methyl-1-butenyl, 1, 2-dimethyl-2-propenyl, 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, 2-pentenyl, and mixtures thereof, 5-hexenyl, 1-methyl-4-pentenyl, 1-ethyl-3-butenyl, 1- (isobutyl) ethenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-2-propenyl, 1- (isopropyl) -2-propenyl, 2-methyl-2-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1, 3-dimethyl-2-butenyl, 1-dimethyl-3-butenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 2-dimethyl-3-butenyl, 1- (isobutyl) ethenyl, methyl-2-pentenyl, methyl-3-butenyl, methyl-2-pentenyl, methyl-3-butenyl, methyl-pentenyl, 1, 3-dimethyl-3-butenyl, 1, 2-trimethyl-2-propenyl, 1, 5-hexadienyl, 1-vinyl-3-butenyl or 2, 4-hexadienyl.

In the present invention, "C" is not particularly limited₂～C₇The alkynyl group "represents a linear or branched alkynyl group having 2 to 7 carbon atoms, and examples thereof include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 1-methyl-2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1-ethyl-2-propynyl group, a 2-pentynyl group, a 3-pentynyl group, a 1-methyl-2-butynyl group, a 4-pentynyl group, a 1-methyl-3-butynyl group, a 2-methyl-3-butynyl group, a 1-hexynyl group, a 1- (n-propyl) -2-propynyl group, a 2-hexynyl group, a 1-ethyl-2-butynyl group, a 3-hexynyl group, a 1-methyl-2-pentynyl group, a, 1-methyl-3-pentynyl group, 4-methyl-1-pentynyl group, 3-methyl-1-pentynyl group, 5-hexynyl group, 1-ethyl-3-butynyl group, 1-ethyl-1-methyl-2-Propynyl, 1- (isopropyl) -2-propynyl, 1-dimethyl-2-butynyl or 2, 2-dimethyl-3-butynyl, 1-heptynyl, 1- (n-butyl) -2-propynyl, 1- (sec-butyl) -2-propynyl, 1-isobutyl-2-propynyl, 2-heptynyl, 3-heptynyl, 1-methyl-2-hexynyl, 4-methyl-2-hexynyl, 5-methyl-2-hexynyl, 6-heptynyl, 1-diethyl-2-propynyl, 1-methyl-1-propyl-2-propynyl, 1-isopropyl-1-methyl-2-propynyl, 1-dimethyl-2-propynyl, 1, 1-dimethyl-2-pentynyl, 1, 4-dimethyl-2-pentynyl or 4, 4-dimethyl-2-pentynyl.

In the present invention, "C" is not particularly limited₁～C₆The "haloalkyl group" represents a straight-chain or branched alkyl group having 1 to 6 carbon atoms which is substituted with the same or different 1 to 13 halogen atoms, and represents, for example, a haloalkyl group, and includes: fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, iodomethyl, chlorodifluoromethyl, dichlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1-difluoroethyl, 2,2, 2-trifluoroethyl, 1,2, 2-tetrafluoroethyl, pentafluoroethyl, 1-chloroethyl, 2-chloroethyl, 1-dichloroethyl, 2,2, 2-trichloroethyl, 1,2, 2-tetrachloroethyl, pentachloroethyl, 1-bromoethyl, 2,2, 2-tribromoethyl, 1-iodoethyl, 2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl group, 1-fluoropropyl group, 2-fluoropropyl group, 3-fluoropropyl group, 1-difluoropropyl group, 2-difluoropropyl group, 3,3, 3-trifluoropropyl group, 2,3,3, 3-pentafluoropropyl group, 1,2,3,3, 3-hexafluoropropyl group, heptafluoropropyl group, 1-fluoropropan-2-yl group, 2-fluoropropan-2-yl group, 1-difluoropropan-2-yl group, 1, 2-difluoropropan-2-yl group, 1, 3-difluoropropan-2-yl group, 1,2, 3-trifluoropropan-2-yl group, 1,3, 3-tetrafluoropropan-2-yl group, 1,1,1,3,3, 3-hexafluoropropan-2-yl, heptafluoropropan-2-yl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 1, 1-dichloropropyl, 2-dichloropropyl, 3,3, 3-trichloropropyl, 2,3,3, 3-pentachloropropyl, heptachloropropyl, 1-chloropropan-2-yl, 2-chloropropan-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-tetra-chloropropane-2-ylChloropropan-2-yl, 1,1,1,3,3, 3-hexachloropropan-2-yl, heptachloropropan-2-yl, 1-bromopropyl, 2-bromopropyl, 3-bromopropyl, 1-bromopropan-2-yl, 2-bromopropan-2-yl, 1-iodopropyl, 2-iodopropyl, 3-iodopropyl, 1-iodopropan-2-yl, 2-iodopropan-2-yl, 1-fluorobutyl, 2-fluorobutyl, 3-fluorobutyl, 4, 4-difluorobutyl, 4,4, 4-trifluorobutyl, 4,4, 4-trifluoro-3-methylbutyl, 3,3,4,4, 4-pentafluorobutyl, 3-hexachloropropan-2-yl, heptafluoropropan-2-yl, 1-bromopropyl, 2-iodopropyl, 2-iodopropan-2-yl, 2-iodopropan-, 2,2,3,4,4, 4-hexafluorobutyl, 2,3,3,4,4, 4-heptafluorobutyl, nonafluorobutyl, 1,1, 1-trifluorobutan-2-yl, 4,4, 4-trifluorobutan-2-yl, 3,3,4,4, 4-pentafluorobutan-2-yl, nonafluorobutan-2-yl, 1,1,1,3,3, 3-hexafluoro-2- (trifluoromethyl) propan-2-yl, 1-chlorobutyl, 2-chlorobutyl, 3-chlorobutyl, 4, 4-dichlorobutyl, 4,4, 4-trichlorobutyl, nonachlorobutyl, 1,1, 1-trichlorobutan-2-yl, 4,4, 4-trichlorobutan-2-yl, Nonachlorobutan-2-yl, 1-bromobutyl, 2-bromobutyl, 3-bromobutyl, 4-bromobutyl, 1-iodobutyl, 2-iodobutyl, 3-iodobutyl, 4-chloro-1, 1,2,2,3,3,4, 4-octafluorobutyl, 4-bromo-1, 1,2,2,3,3,4, 4-octafluorobutyl, 1-fluoropentyl, 2-fluoropentyl, 3-fluoropentyl, 4-fluoropentyl, 5,5, 5-trifluoropentyl, 4,4,5, 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 group, undecafluoropentyl group, 1-chloropentyl group, 2-chloropentyl group, 3-chloropentyl group, 4-chloropentyl group, 5,5, 5-trichloropentyl group, 4,4,5, 5-pentachloropentyl group, 3,3,4,4,5,5, 5-heptachloropentyl group, 2,3,3,4,4,5,5, 5-nonachloropentyl group, undecafloropentyl group, 1-bromopentyl group, 2-bromopentyl group, 3-bromopentyl group, 4-bromopentyl group, 5-iodopentyl group, 1-fluorohexyl group, 2-fluorohexyl group, 3-fluorohexyl group, 4-fluorohexyl group, 5-fluorohexyl group, 6,6, 6-trifluorohexyl group, 5,5,6,6, 6-pentafluorohexyl, 4,4,5,5,6,6, 6-heptafluorohexyl, 3,3,4,4,5,5,6,6, 6-nonafluorohexyl, 2,3,3,4,4,5, 6,6, 6-undecafluorohexyl, 2,3,3,4,4,5,5,6, 6-decafluorohexyl, tridecafluorohexyl, 1-chlorohexyl, 2-chlorohexyl, 3-chlorohexyl, 4-chlorohexyl, 5-chlorohexyl, 6-bromohexyl, 5-iodohexyl or 6-iodohexyl.

In the present invention, "C" is not particularly limited₁～C₁₂HalogenatedThe "alkyl group" represents a linear or branched alkyl group having 1 to 12 carbon atoms substituted with the same or different 1 to 25 halogen atoms, for example, except for the above "C₁～C₆Examples of the "haloalkyl group" include: 2,2,3,4,4,6,6, 6-octafluoro-3, 5, 5-tris (trifluoromethyl) hexyl, 7,7, 7-trifluoroheptyl, 1H-perfluoroheptyl, 1H,2H,2H,3H, 3H-perfluoroheptyl, 1H, 7H-perfluoroheptyl, 2- (perfluoro-3-methylbutyl) ethyl, 1H-perfluorooctyl, 1H,2H,2H, 2H,3H, 3H-perfluorooctyl, 6- (perfluorohexyl) ethyl, 1H, 8H-perfluorooctyl, 1H-perfluorononyl, 1H,2H, 3H, 3H-perfluorooctyl, 6- (perfluorohexyl) ethyl, 1H, 8H-perfluorooctyl, 1H,1H,2H, 2H-perfluorononyl, 1H,2H,2H,3H, 3H-perfluorononyl, 6- (perfluoro-1-methylethyl) hexyl, 1H, 9H-perfluorononyl, 1H-perfluorodecyl, 1H,2H,2H,3H, 3H-perfluorodecyl, 6- (perfluorobutyl) hexyl, 1H, 9H-perfluorodecyl, perfluorodecyl or the like.

In the present invention, "C" is not particularly limited₁～C₆Alkoxy "denotes an alkyl moiety as defined above (C)₁～C₆Examples of the alkyl) -O-group include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1-ethylpropoxy, 1-dimethylpropoxy, 1, 2-dimethylpropoxy and n-hexoxy groups.

In the present invention, "C" is not particularly limited₁～C₆Haloalkoxy "means an alkyl halide moiety as defined above (C)₁～C₆Haloalkane) -O-group, for example, difluoromethoxy, dichloromethoxy, trifluoromethoxy, trichloromethoxy, tribromomethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 1-chloroethoxy, 2-chloroethoxy, 1-bromoethoxy, 2, 2-difluoroethoxy, 1, 2-dichloroethoxy, 2,2, 2-trifluoroethoxy, 2,2, 2-trichloroethoxy, 1,2, 2-tetrafluoroethoxy, pentafluoroethoxy, 2-bromo-2-chloroethoxyEthoxy, 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, 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-chloro-1, 2,2, 2-tetrafluoroethoxy, 1-chloro-1-chloroethoxy, 2-bromopropoxy, 3-methylpropoxy, 3-iodopropoxy, 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, 1,2,3,3, 3-hexafluoropropoxy, 2-chlorobutoxy, 3-chlorobutoxy, 4-chlorobutoxy, 2-chloro-1, 1-dimethylethoxy, 4-bromobutoxy, 3-bromo-2-methylpropoxy, 2-bromo-1, 1-dimethylethoxy, 2, 2-dichloro-1, 1-dimethylethoxy, 2-chloro-1-chloromethyl-2-methylethoxy, 2-chloro-1-2-fluoropropoxy, 2,2, 2-trifluoro-, 4,4, 4-trifluorobutoxy group, 3,3, 3-trifluoro-1-methylpropoxy group, 3,3, 3-trifluoro-2-methylpropoxy group, 2,3, 4-trichlorobutoxy group, 2,2, 2-trichloro-1, 1-dimethylethoxy group, 4-chloro-4, 4-difluorobutoxy group, 4, 4-dichloro-4-fluorobutoxy group, 4-bromo-4, 4-difluorobutoxy group, 2, 4-dibromo-4, 4-difluorobutoxy group, 3, 4-dichloro-3, 4, 4-trifluorobutoxy group, 3, 3-dichloro-4, 4, 4-trifluorobutoxy group, 4-bromo-3, 3,4, 4-tetrafluorobutoxy group, t, 4-bromo-3-chloro-3, 4, 4-trifluorobutoxy, 2,2,3,3,4, 4-hexafluorobutoxy, 2,2,3,4,4, 4-hexafluorobutoxy, 2,2, 2-trifluoro-1-methyl-1-trifluoromethylethoxy, 3,3, 3-trifluoro-2-trifluoromethylpropoxy, 2,2,3,3,4,4, 4-heptafluorobutoxy, 3,3,4,4, 4-pentafluoro-2-butoxy, 2,3,3, 3-tetrafluoro-2-trifluoromethylpropoxy, 1,2,2,3,3,4, 4-octafluorobutoxy, nonafluorobutoxy, perfluoro-tert-butoxy, 4-chloro-1, 1,2,2,3,3,4, 4-octafluorobutoxy, 5,5, 5-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, 2,3,3,4,4,5,5, 5-nonafluoropentyloxy, 2,3,3,4,4,5, 5-octafluoropentyloxy, perfluoropentyloxy, 4,4,5,5, 5-pentafluoro-2-butoxy, 2-bis (trifluoromethyl) propoxy, 2,3,4,4, 5,5,6,6, 6-undecafluorohexyloxy, 3,3,4,4,5,5,6, 6-nonafluorohexyloxy, 4,4,5,5,6,6, 6-heptafluorohexyloxy, 2,3,3,4,4,5,5,6, 6-decafluorohexyloxyA group such as a4, 4, 4-trifluoro-3, 3-bis (trifluoromethyl) butoxy group or a perfluorohexyloxy group.

In the present invention, "C" is not particularly limited₃～C₆The "cycloalkyl group" represents a cycloalkyl group having 3 to 6 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

In the present invention, "C₃～C₆Cycloalkyl radical C₂～C₆Alkynyl "means that the cycloalkyl moiety is as defined above (C)₃～C₆Cycloalkyl) - (C)₂～C₆Examples of the alkynyl) -group include groups such as a 3-cyclopropyl-2-propynyl group, a 3-cyclobutyl-2-propynyl group, a 3-cyclopentyl-2-propynyl group, a 3-cyclohexyl-2-propynyl group, a 3-cyclopropyl-1-methyl-2-propynyl group, a 3-cyclobutyl-1-methyl-2-propynyl group, a 3-cyclopentyl-1-methyl-2-propynyl group and a 3-cyclohexyl-1-methyl-2-propynyl group.

In the present invention, "C₁～C₆Alkylthio "denotes an alkyl moiety as defined above (C)₁～C₆Examples of the alkyl) -S-group include methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio and the like.

In the present invention, "C₁～C₆Alkylsulfinyl "denotes (C) an alkyl moiety as defined above₁～C₆Examples of the alkyl) -SO-group include, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl and tert-butylsulfinyl groups.

In the present invention, "C₁～C₆Alkylsulfonyl "means that the alkyl moiety is as defined above (C)₁～C₆Alkyl) -SO₂Examples of the "yl" group include, for example, a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, an isopropylsulfonyl group, an n-butylsulfonyl group, an isobutylsulfonyl group, a sec-butylsulfonyl group, and a tert-butylsulfonyl group.

In the present invention, "mono (C)₁～C₆Alkyl) amino "means that the alkyl moiety is (C) as defined above₁～C₆Examples of the alkyl group) -NH-group include a methylamino group, an ethylamino group, an n-propylamino group, an isopropylamino group and the like.

In the present invention, "two (C)₁～C₆Alkyl) amino "means that the alkyl moiety is (C) as defined above₁～C₆Alkyl radical)₂Examples of the-N-group include a dimethylamino group, a diethylamino group, and an N-ethyl-N-methylamino group.

In the present invention, "C₁～C₆Alkoxy radical C₁～C₆Alkyl "denotes an alkoxy moiety as defined above (C)₁～C₆Alkoxy group) - (C₁～C₆Examples of the alkyl) -group include, for example, a methoxymethyl group, a 1-methoxyethyl group, a 2-ethoxyethyl group, a 2-methoxypropyl group, a 3-methoxypropyl group, a 2-ethoxypropyl group, a 3-ethoxypropyl group, a 1-methyl-3-methoxybutyl group and a 3-butoxybutyl group.

In the present invention, "C₁～C₆Alkoxy radical C₁～C₆Haloalkyl "means an alkoxy moiety as defined above (C)₁～C₆Alkoxy group) - (C₁～C₆Examples of the "haloalkyl" -group include groups such as a 2-methoxy-1, 1, 2-trifluoroethyl group and a 2-ethoxy-1, 1, 2-trifluoroethyl group.

In the present invention, "C₁～C₆Halogenoalkoxy radical C₁～C₆Alkyl represents a haloalkoxy moiety as defined above (C)₁～C₆Haloalkoxy) - (C₁～C₆Examples of the alkyl) -group include, for example, a group such as a 2- (difluoromethoxy) ethyl group, a 2- (trifluoromethoxy) ethyl group, a 2- (2, 2-difluoroethoxy) ethyl group, and a 2- (2,2, 2-trifluoroethoxy) ethyl group.

In the present invention, "C₁～C₆Halogenoalkoxy radical C₁～C₆Haloalkyl "means a haloalkoxy moiety as defined above (C)₁～C₆Haloalkoxy) - (C₁～C₆Haloalkyl) -radicalExamples of the group include groups such as 1,1, 2-trifluoro-2- (trifluoromethoxy) ethyl group, 1, 2-trifluoro-2- (pentafluoroethoxy) ethyl group, and 1,1, 2-trifluoro-2- (heptafluoropropoxy) ethyl group.

In the present invention, "C" is not particularly limited₂～C₆The "haloalkynyl group" represents a linear or branched alkynyl group having 2 to 6 carbon atoms which is substituted with the same or different 1 to 9 halogen atoms, and examples thereof include fluoroethynyl group, chloroethynyl group, bromoethynyl group, iodoethynyl group, 3-fluoro-2-propynyl group, 3-chloro-2-propynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group, 4-fluoro-3-butynyl group, 4-chloro-3-butynyl group, 4-bromo-3-butynyl group, 4-iodo-3-butynyl group, 4, 4-difluoro-2-butynyl group, 4, 4-dichloro-2-butynyl group, 4,4, 4-trifluoro-2-butynyl group, 4-bromo-3-butynyl group, 4-iodo-3-butynyl group, 4,4-, 4,4, 4-trichloro-2-butynyl, 3-fluoro-1-methyl-2-propynyl, 3-chloro-1-methyl-2-propynyl, 5-fluoro-4-pentynyl, 5-chloro-4-pentynyl, 5,5, 5-trifluoro-3-pentynyl, 5,5, 5-trichloro-3-pentynyl, 4-fluoro-2-methyl-3-butynyl, 4-chloro-2-methyl-3-butynyl, 6-fluoro-5-hexynyl, 6-chloro-5-hexynyl, 6,6, 6-trifluoro-4-hexynyl, 6,6, 6-trichloro-4-hexynyl, 6-fluoro-4-hexynyl, 5-fluoro-3-methyl-4-pentynyl, 5-chloro-3-methyl-4-pentynyl, and the like.

In the present invention, "C" is not particularly limited₂～C₆The "haloalkenyl group" represents a linear or branched alkenyl group having 2 to 6 carbon atoms substituted with the same or different 1 to 11 halogen atoms, and examples thereof include 1-fluorovinyl group, 2-fluorovinyl group, 1, 2-difluorovinyl group, 2-difluorovinyl group, trifluorovinyl group, 1-chloroethenyl group, 2-chloroethenyl group, 1, 2-dichlorovinyl group, 2-dichlorovinyl group, trichloroethyl group, 1, 2-dibromovinyl group, 2-dibromovinyl group, tribromovinyl group, 1, 2-diiodovinyl group, 2-diiodovinyl group, triiodovinyl group, 1-fluoro-2-propenyl group, 2-fluoro-2-propenyl group, 3-fluoro-2-propenyl group, and 2, 3-difluoro-2-propenyl group, 3, 3-difluoro-1-propenyl group, 2,3, 3-trifluoro-2-propenyl group, 3,3, 3-trifluoro-1-propenyl group, 2-chloro-3, 3, 3-trifluoro-1-propenyl group, 1,2,3,3, 3-pentafluoro-1-propenyl group, 1-chloro-2-propenyl group, 2-chloro-2-propenyl group, 3-chloro-2-propenyl group, 2, 3-dichloro-2-propenyl group, 3, 3-dichloro-2-propenyl group-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-difluoro-1-propen-2-yl, 3,3, 3-trifluoro-1-propen-2-yl, 3,3, 3-trichloro-1-propen-2-yl, 4-fluoro-3-butenyl, 4-difluoro-3-buten-2-yl, 3,3, 3-dichloro-2-propenyl, 3, 3-di-bromo-2-propenyl, 3, 3-dibromo-2-propenyl, 4-fluoro-3-butenyl, 4,4,4, 4-trifluoro-2-butenyl, 3,4, 4-trifluoro-3-butenyl, 2-trifluoromethyl-2-propenyl, 2-trifluoromethyl-3, 3-difluoro-2-propenyl, 4,4, 4-trifluoro-3-chloro-2-butenyl, 4, 4-dichloro-3-butenyl, 4,4, 4-trichloro-2-butenyl, 2-trichloromethyl-2-propenyl, 5, 5-difluoro-4-pentenyl, 4,5, 5-trifluoro-4-pentenyl, 5,5, 5-trifluoro-3-pentenyl, 4,4, 4-trifluoro-3-methyl-2-butenyl, 4,4, 4-trifluoro-3-pentenyl, 4-chloro-2-butenyl, 4, 4-dichloro-3-butenyl, 4,4,4, 4, 4-trifluoro-3-trifluoromethyl-2-butenyl, 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.

In the present invention, "C" is not particularly limited₃～C₆The "halocycloalkyl group" represents a cycloalkyl group having 3 to 6 carbon atoms substituted with the same or different 1 to 11 halogen atoms, and examples thereof include 1-fluorocyclopropyl group, 2-difluorocyclopropyl group, 2,3, 3-tetrafluorocyclopropyl group, 1-chlorocyclopropyl group, 2-dichlorocyclopropyl group, 2,3, 3-tetrachlorocyclopropyl group, 2-dibromocyclopropyl group, 2-diiodocyclopropyl group, 1-fluorocyclobutyl group, 2-fluorocyclobutyl group, 3, 3-difluorocyclobutyl group, heptafluorocyclobutyl group, 2-chlorocyclobutyl group, 3, 3-dichlorocyclobutyl group, 3, 3-dibromocyclobutyl group, 3, 3-diiodocyclobutyl group, 1-fluorocyclopentyl group, 2-fluorocyclopentyl group, 3-fluorocyclopentyl group, 2-difluorocyclopentyl group, 3-difluorocyclopentyl group, nonafluorocyclopentyl group, 2-dichlorocyclopentyl group, 3-dichlorocyclopentyl group, 2-dibromocyclopentyl group, 3-dibromocyclopentyl group, 2-diiodocyclopentyl group, 3-diiodocyclopentyl group, 1-fluorocyclohexyl group, 2-fluorocyclohexyl group, 3-fluorocyclohexyl group, 4-fluorocyclohexyl group, 2-difluorocyclohexyl group, 3-difluorocyclohexyl group, 4-difluorocyclohexyl group, 1-chlorocyclohexyl group, 2-difluorocyclopentyl group, 3-difluorocyclopentyl group, nonafluorocyclopentyl group, 2-,2-chlorocyclohexyl group, 3-chlorocyclohexyl group, 4-chlorocyclohexyl group, 2-dichlorocyclohexyl group, 3-dichlorocyclohexyl group, 4-dichlorocyclohexyl group, 3-dibromocyclohexyl group, 4-dibromocyclohexyl group, 3-diiodocyclohexyl group, 4-diiodocyclohexyl group and the like.

In the present invention, "C" is not particularly limited₁～C₆Haloalkyl C₃～C₆Cycloalkyl "denotes a haloalkyl moiety and a cycloalkyl moiety as defined above (C)₁～C₆Haloalkyl) - (C)₃～C₆Cycloalkyl) groups, for example, mention may be made of: 2-trifluoromethylcyclopropyl group, 2-trifluoromethylcyclobutyl group, 3-trifluoromethylcyclobutyl group, 2-trifluoromethylcyclopentyl group, 3-trifluoromethylcyclopentyl group, 2-trifluoromethylcyclohexyl group, 3-trifluoromethylcyclohexyl group, or 4-trifluoromethylcyclohexyl group.

In the present invention, "C" is not particularly limited₃～C₆Cycloalkyl radical C₁～C₆Alkyl represents a cycloalkyl moiety and the alkyl moiety is as defined above (C)₃～C₆Cycloalkyl) - (C)₁～C₆Alkyl) groups, for example, mention may be made of: a cyclopropylmethyl group, a cyclobutylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a 1-cyclopropylethyl group, a 2-cyclobutylethyl group, a 2-cyclopentylethyl group, a 2-cyclohexylethyl group, or the like.

In the present invention, "C" is not particularly limited₃～C₆Halogenocycloalkyl C₁～C₆Alkyl represents a halogenated cycloalkyl moiety as defined above (C)₃～C₆Halocycloalkyl) - (C₁～C₆Alkyl) -radicals, for example, mention may be made of: 2, 2-difluorocyclopropylmethyl group, 2-dichlorocyclopropylmethyl group, 1- (2, 2-difluorocyclopropyl) ethyl group, 2- (2, 2-difluorocyclopropyl) ethyl group, 1- (2, 2-dichlorocyclopropyl) ethyl group, 2- (2, 2-difluorocyclopropyl) propyl group, 3, 3-difluorocyclobutylmethyl group, 2,3, 3-tetrafluorocyclobutylmethyl group, 2- (2,2,3, 3-tetrafluorocyclobutyl) ethyl group, 2- (3, 3-difluorocyclobutyl) propyl group, 3, 3-difluorocyclopentylmethyl group, 2- (3, 3-difluorocyclopentyl) propyl group and the like.And (4) clustering.

In the present invention, "C" is not particularly limited₁～C₆Alkylthio group C₁～C₆Alkyl "denotes an alkyl moiety as defined above (C)₁～C₆Alkyl) -S- (C₁～C₆Alkyl) -radicals, for example, mention may be made of: methylthiomethyl, ethylthiomethyl, n-propylthiomethyl, isopropylthiomethyl, 1- (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- (methylthio) propyl, 1- (ethylthio) propyl, 2- (ethylthio) propyl, 3- (ethylthio) propyl, 1- (n-propylthio) propyl, 2- (n-propylthio) propyl, 3- (n-propylthio) propyl, 1- (methylthio) butyl, 2- (methylthio) butyl, 3- (methylthio) butyl, 1- (methylthio) butyl, 4- (methylthio) butyl, 1- (methylthio) pentyl, 2- (methylthio) pentyl, 3- (methylthio) pentyl, 4- (methylthio) pentyl, 5- (methylthio) pentyl, 2- (n-butylthio) ethyl, 2- (isobutylthio) ethyl, sec-butylthioethyl, 2- (tert-butylthio) ethyl, pentylthiomethyl or hexylthiomethyl.

In the present invention, "C" is not particularly limited₁～C₆Alkylsulfinyl radical C₁～C₆Alkyl "denotes an alkyl moiety as defined above (C)₁～C₆Alkyl) -S (═ O) - (C)₁～C₆Alkyl) -radicals, for example, mention may be made of: methylsulfinylmethyl, ethylsulfinylmethyl, n-propylsulfinylmethyl, isopropylsulfinylmethyl, 1- (methylsulfinyl) ethyl, 2- (ethylsulfinyl) ethyl, 1- (n-propylsulfinyl) ethyl, 2- (n-propylsulfinyl) ethyl, 1- (isopropylsulfinyl) ethyl, 2- (isopropylsulfinyl) ethyl, 1- (methylsulfinyl) propyl, 2- (methylsulfinyl) propyl, 3- (methylsulfinyl) propyl, 1- (ethylsulfinyl) propyl, 2- (ethylsulfinyl) propyl, 3- (ethylsulfinyl) propyl, 1- (n-propylsulfinyl) propyl, 2- (n-propylsulfinyl) propyl, methyl-, ethyl-, n-propylsulfinyl-, ethyl-, n-propylsulfinyl-, ethyl-, propyl, 3- (n-propylsulfinyl) propaneA group such as 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- (isobutylsulfinyl) ethyl, sec-butylsulfinylethyl, 2- (tert-butylsulfinyl) ethyl, pentylsulfinylmethyl or hexylsulfinylmethyl.

In the present invention, "C" is not particularly limited₁～C₆Alkylsulfonyl radical C₁～C₆Alkyl "denotes an alkyl moiety as defined above (C)₁～C₆Alkyl) -S (═ O)₂-(C₁～C₆Alkyl) -radicals, for example, mention may be made of: methylsulfonylmethyl, ethylsulfonylmethyl, n-propylsulfonylmethyl, isopropylsulfonylmethyl, 1- (methylsulfonyl) ethyl, 2- (ethylsulfonyl) ethyl, 1- (n-propylsulfonyl) ethyl, 2- (n-propylsulfonyl) ethyl, 1- (isopropylsulfonyl) ethyl, 2- (isopropylsulfonyl) ethyl, 1- (methylsulfonyl) propyl, 2- (methylsulfonyl) propyl, 3- (methylsulfonyl) propyl, 1- (ethylsulfonyl) propyl, 2- (ethylsulfonyl) propyl, 3- (ethylsulfonyl) propyl, 1- (n-propylsulfonyl) propyl, 2- (n-propylsulfonyl) propyl, 3- (n-propylsulfonyl) propyl, methyl-, ethyl-, n-propylsulfonyl-, ethyl-, propyl-, 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, sec-butylsulfonylethyl, 2- (tert-butylsulfonyl) ethyl, pentylsulfonylmethyl, or hexylsulfonylmethyl.

In the present invention, "C₁～C₆Halogenoalkylthio C₁～C₆Alkyl "denotes an alkyl halide moiety as defined above (C)₁～C₆Haloalkyl) -S- (C)₁～C₆Alkyl) -radicals, for example, mention may be made of: 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- (3,3, 3-trifluoropropylthio) propyl, 4- (trifluoromethylthio) butyl or 5- (trifluoromethylthio) pentyl.

In the present invention, "C₁～C₆Halogenoalkylsulfinyl C₁～C₆Alkyl "denotes an alkyl halide moiety as defined above (C)₁～C₆Haloalkyl) -S (═ O) - (C)₁～C₆Alkyl) -radicals, for example, mention may be made of: 2- (difluoromethylsulfinyl) ethyl group, 2- (trifluoromethylsulfinyl) ethyl group, 2- (2, 2-difluoroethylsulfinyl) ethyl group, 2- (2,2, 2-trifluoroethylsulfinyl) ethyl group, 2- (3, 3-difluoropropylsulfinyl) ethyl group, 2- (3,3, 3-trifluoroethylsulfinyl) ethyl group, 3- (difluoromethylsulfinyl) propyl group, 3- (trifluoromethylsulfinyl) propyl group, 3- (2, 2-difluoroethylsulfinyl) propyl group, 3- (2,2, 2-trifluoroethylsulfinyl) propyl group, 3- (3, 3-difluoropropylsulfinyl) propyl group, 3- (3,3, 3-trifluoropropylsulfinyl) propyl group, methyl ethyl group, 2- (2, 2-difluoroethylsulfinyl) ethyl group, 3,4- (trifluoromethylsulfinyl) butyl or 5- (trifluoromethylsulfinyl) pentyl.

In the present invention, "C₁～C₆Haloalkylsulfonyl C₁～C₆Alkyl "denotes an alkyl halide moiety as defined above (C)₁～C₆Haloalkyl) -S (═ O)₂-(C₁～C₆Alkyl) -radicals, for example, mention may be made of: 2- (difluoromethylsulfonyl) ethyl, 2- (trifluoromethylsulfonyl) ethyl, 2- (2, 2-difluoroethylsulfonyl) ethyl, 2- (2,2, 2-trifluoroethylsulfonyl) ethyl, 2- (3, 3-difluoropropylsulfonyl) ethyl, 2- (3,3, 3-trifluoroethylsulfonyl) ethyl, 3- (difluoromethylsulfonyl) propyl, 3- (trifluoromethylsulfonyl) propyl, 3- (2, 2-difluoroethylsulfonyl) propyl, 3- (2,2, 2-trifluoroethylsulfonyl) propylA group such as a 3- (3, 3-difluoropropylsulfonyl) propyl group, a 3- (3,3, 3-trifluoropropylsulfonyl) propyl group, a 4- (trifluoromethylsulfonyl) butyl group or a 5- (trifluoromethylsulfonyl) pentyl group.

In the present invention, "mono (C)₁～C₆Alkyl) aminocarbonyl "means that the alkyl moiety is (C) as defined above₁～C₆Alkyl) -NH-C (═ O) -yl, for example, there may be mentioned: a methylaminocarbonyl group, an ethylaminocarbonyl group, an n-propylaminocarbonyl group, an isopropylaminocarbonyl group, an n-butylaminocarbonyl group, an isobutylaminocarbonyl group, a sec-butylaminocarbonyl group, a tert-butylaminocarbonyl group, an n-pentylaminocarbonyl group, a 1-methylbutylaminocarbonyl group, a 2-methylbutylaminocarbonyl group, a 3-methylbutylaminocarbonyl group, a 1-ethylpropylaminocarbonyl group, a 1, 1-dimethylpropylaminocarbonyl group, a 1, 2-dimethylpropylaminocarbonyl group, a 2, 2-dimethylpropylaminocarbonyl group, or a n-hexylaminocarbonyl group.

In the present invention, "two (C)₁～C₆Alkyl) aminocarbonyl "means that the alkyl moiety is (C) as defined above₁～C₆Alkyl radical)₂N — C (═ O) -yl, where 2 alkyl groups may differ from each other, such as for example: dimethylaminocarbonyl, diethylaminocarbonyl, di (N-propyl) aminocarbonyl, diisopropylaminocarbonyl, dibutylaminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-isopropyl-N-methylaminocarbonyl, N-butyl-N-methylaminocarbonyl, N- (sec-butyl) -N-methylaminocarbonyl, N-isobutyl-N-methylaminocarbonyl, N-pentyl-N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N-isopropylaminocarbonyl, or N-ethyl-N-butylaminocarbonyl.

In the present invention, "mono (C)₁～C₆Alkyl) aminothiocarbonyl "means that the alkyl moiety is (C) as defined above₁～C₆Alkyl) -NH-C (═ S) -yl, for example, there may be mentioned: methylaminothiocarbonyl, ethylaminothiocarbonyl, n-propylaminothiocarbonyl, isopropylaminothiocarbonyl, n-butylaminothiocarbonyl, isobutylaminothiocarbonyl, sec-butylaminothiocarbonyl, tert-butylaminothiocarbonyl, n-pentyleneA group such as alkylaminothiocarbonyl, 1-methylbutylaminothiocarbonyl, 2-methylbutylaminothiocarbonyl, 3-methylbutylaminothiocarbonyl, 1-ethylpropylaminothiocarbonyl, 1-dimethylpropylaminothiocarbonyl, 1, 2-dimethylpropylaminothiocarbonyl, 2-dimethylpropylaminothiocarbonyl or n-hexylaminothiocarbonyl.

In the present invention, "two (C)₁～C₆Alkyl) aminothiocarbonyl "means that the alkyl moiety is (C) as defined above₁～C₆Alkyl radical)₂-N-C (═ S) -yl, where the 2 alkyl groups may differ, such as to list: dimethylaminothiocarbonyl, diethylaminothiocarbonyl, di (N-propyl) aminothiocarbonyl, diisopropylaminothiocarbonyl, dibutylaminothiocarbonyl, N-ethyl-N-methylaminothiocarbonyl, N-methyl-N-propylaminoylthiocarbonyl, N-isopropyl-N-methylaminothiocarbonyl, N-butyl-N-methylaminothiocarbonyl, N- (sec-butyl) -N-methylaminothiocarbonyl, N-isobutyl-N-methylaminothiocarbonyl, N-pentyl-N-methylaminothiocarbonyl, N-ethyl-N-propylaminothiocarbonyl, N-ethyl-N-isopropylaminothiocarbonyl or N-ethyl-N-butylaminothiocarbonyl.

In the present invention, "C₁～C₆Alkyl carbonyl radical C₁～C₆Alkyl "denotes an alkyl moiety as defined above (C)₁～C₆Alkyl) -C (═ O) - (C)₁～C₆Alkyl) groups, for example, mention may be made of: acetonyl, propionylmethyl, 2-methylpropionylmethyl, trimethylacetylmethyl, 2-acetylethyl, 2-propionylethyl, 2- (2-methylpropionyl) ethyl, 2-trimethylacetylethyl, 3-acetylpropyl, 3-propionylpropyl, 3- (2-methylpropionyl) propyl or 3-trimethylacetylpropyl, and the like.

In the present invention, "C₁～C₆Halogenoalkylcarbonyl group C₁～C₆Alkyl "denotes an alkyl moiety as defined above (C)₁～C₆Haloalkyl) -C (═ O) - (C)₁～C₆Alkyl) groups, for example, mention may be made of: 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 the like.

In the present invention, "C₁～C₆Alkoxycarbonyl radical C₁～C₆Alkyl "denotes an alkoxy moiety as defined above (C)₁～C₆Alkoxy) -C (═ O) - (C)₁～C₆Alkyl) -radicals, for example, mention may be made of: a methoxycarbonylmethyl group, an ethoxycarbonylmethyl group, an n-propoxycarbonylmethyl group, an isopropoxycarbonylmethyl group, a tert-butoxycarbonylmethyl group, a 1- (methoxycarbonyl) ethyl group, a 2- (methoxycarbonyl) ethyl group, a 1- (ethoxycarbonyl) ethyl group, a 2- (ethoxycarbonyl) ethyl group, a 1- (methoxycarbonyl) -1-methylethyl group, a 1- (ethoxycarbonyl) -1-methylethyl group, or a 2- (tert-butoxycarbonyl) ethyl group.

In the present invention, "aminocarbonyl group C₁～C₆Alkyl "denotes an alkyl moiety as defined above for H₂N-C(＝O)-(C₁～C₆Examples of the alkyl) -group include a carbamoylmethyl group, a 1-carbamoylethyl group, and a 2-carbamoylethyl group.

In the present invention, "mono (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl "denotes an alkyl moiety as defined above (C)₁～C₆Alkyl) -NH-C (═ O) - (C)₁～C₆Alkyl) -radicals, for example, mention may be made of: n-methylcarbamoylmethyl, N-ethylcarbamoylmethyl, N- (tert-butyl) carbamoylmethyl and the like.

In the present invention, "mono (C)₁～C₆Haloalkyl) aminocarbonyl C₁～C₆Alkyl "denotes an alkyl halide moiety as defined above (C)₁～C₆Haloalkyl) -NH-C (═ O) - (C)₁～C₆Alkyl) -radicals, for example, mention may be made of: n- (2, 2-difluoroethyl) carbamoylmethyl, N- (2,2, 2-trifluoroethyl) carbamoylmethyl, 1- { N- (2, 2-difluoroethyl) carbamoyl } ethyl,1- { N- (2, 2-trifluoroethyl) carbamoyl]Ethyl, 1- { N- (2, 2-difluoroethyl) carbamoyl } -1-methylethyl or 1- { N- (2, 2-trifluoroethyl) carbamoyl } -1-methylethyl, and the like.

In the present invention, "mono (C)₃～C₆Cycloalkyl) aminocarbonyl group C₁～C₆Alkyl "denotes a cycloalkyl moiety as defined above (C)₃～C₆Cycloalkyl) -NH-C (═ O) - (C)₁～C₆Alkyl) -radicals, for example, mention may be made of: n-cyclopropylcarbamoylmethyl, N-cyclobutylcarbamoylmethyl, N-cyclopentylcarbamoylmethyl or N-cyclohexylcarbamoylmethyl.

In the present invention, "two (C)₁～C₆Alkyl) aminocarbonyl group C₁～C₆Alkyl "denotes an alkyl moiety as defined above (C)₁～C₆Alkyl radical)₂-N-C(＝O)-(C₁～C₆Alkyl) -radicals, for example, mention may be made of: n, N-dimethylcarbamoylmethyl, N-diethylcarbamoylmethyl, N-dipropylcarbamoylmethyl, N-ethyl-N-methylcarbamoylmethyl, N-methyl-N-propylcarbamoylmethyl and the like.

In the present invention, "mono (C)₁～C₆Alkylcarbonyl) amino C₁～C₆Alkyl "denotes an alkyl moiety as defined above (C)₁～C₆Alkyl) -C (═ O) -NH- (C₁～C₆Alkyl) -radicals, for example, mention may be made of: 2- (acetylamino) ethyl group, 2- (propionylamino) ethyl group, 2- (isopropionylamino) ethyl group, 3- (acetylamino) propyl group, 3- (acetylamino) butyl group, and the like.

In the present invention, "mono (C)₁～C₆Alkoxycarbonyl) amino group C₁～C₆Alkyl "denotes an alkoxy moiety as defined above (C)₁～C₆Alkoxy) -C (═ O) -NH- (C₁～C₆Alkyl) -radicals, for example, mention may be made of: 2- (methoxycarbonylamino) ethyl, 2- (ethoxycarbonylamino) ethyl, 2- (tert-butoxycarbonylamino) ethyl and the like.

In the present invention, "mono (C)₁～C₆Alkylsulfonyl) amino C₁～C₆Alkyl "denotes an alkyl moiety as defined above (C)₁～C₆Alkyl) -S (═ O)₂-NH-(C₁～C₆Alkyl) -radicals, for example, mention may be made of: 2- (methylsulfonylamino) ethyl, 2- (ethylsulfonylamino) ethyl, 2- (isopropylsulfonylamino) ethyl, 3- (methylsulfonylamino) propyl, 4- (methylsulfonylamino) butyl, and the like.

In the present invention, "mono (C)₁～C₆Haloalkylsulfonyl) amino C₁～C₆Alkyl "denotes an alkyl moiety as defined above (C)₁～C₆Haloalkyl) -S (═ O)₂-NH-(C₁～C₆Alkyl) -radicals, for example, mention may be made of: 2- (difluoromethylsulfonylamino) ethyl, 2- (trifluoromethylsulfonylamino) ethyl, 3- (difluoromethylsulfonylamino) propyl, 3- (trifluoromethylsulfonylamino) propyl and the like.

In the present invention, "mono (C)₁～C₆Alkyl) aminosulfonyl "means that the alkyl moiety is (C) as defined above₁～C₆Alkyl) -NH-S (═ O) -yl, for example, there may be mentioned: a methylaminosulfonyl group, an ethylaminosulfonyl group, a n-propylaminosulfonyl group, an isopropylaminosulfonyl group, a n-butylaminosulfonyl group, an isobutylaminosulfonyl group, a sec-butylaminosulfonyl group, a tert-butylaminosulfonyl group, a n-pentylaminosulfonyl group, a 1-methylbutylaminosulfonyl group, a 2-methylbutylaminosulfonyl group, a 3-methylbutylaminosulfonyl group, a 1-ethylpropylaminosulfonyl group, a 1, 1-dimethylpropylaminosulfonyl group, a 1, 2-dimethylpropylaminosulfonyl group, a 2, 2-dimethylpropylaminosulfonyl group, a n-hexylaminosulfonyl group or.

In the present invention, "two (C)₁～C₆Alkyl) aminosulfonyl "means that the alkyl moiety is (C) as defined above₁～C₆Alkyl radical)₂-N-S(＝O)₂-radicals in which the 2 alkyl radicals may differ from one another, such as for example: dimethylaminosulfonyl, diethylaminosulfonyl, di (n-propyl) aminosulfonylA group such as a phenyl group, a diisopropyl aminosulfonyl group, a dibutyl aminosulfonyl group, an N-ethyl-N-methylaminosulfonyl group, an N-methyl-N-propylaminosulfonyl group, an N-isopropyl-N-methylaminosulfonyl group, an N-butyl-N-methylaminosulfonyl group, an N- (sec-butyl) -N-methylaminosulfonyl group, an N-isobutyl-N-methylaminosulfonyl group, an N-pentyl-N-methylaminosulfonyl group, an N-ethyl-N-propylaminosulfonyl group, an N-ethyl-N-isopropylaminosulfonyl group or an N-ethyl-N-butylaminosulfonyl group.

In the present invention, "hydroxy group C" is not particularly limited₁～C₆Alkyl "means that the alkyl moiety is (hydroxy) - (C) as defined above₁～C₆Alkyl) groups, for example, mention may be made of: a group such as a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxybutyl group or a 4-hydroxybutyl group.

In the present invention, "hydroxyimino group C" is not particularly limited₁～C₆Alkyl "denotes HO-N ═ (C) with the alkyl moiety defined above₁～C₆Alkyl) groups, for example, mention may be made of: 1- (hydroxyimino) ethyl, 2- (hydroxyimino) ethyl, 1- (hydroxyimino) propyl, 2- (hydroxyimino) propyl, or 3- (hydroxyimino) propyl.

In the present invention, "C" is not particularly limited₁～C₆Alkoxyimino "means an alkyl moiety as defined above (C)₁～C₆Alkyl) -O-N ═ C-groups, such as: a methoxyimino group, an ethoxyimino group, or an isopropoxyimino group.

In the present invention, "C" is not particularly limited₁～C₆Alkoxyimino radical C₁～C₆Alkyl "denotes an alkyl moiety as defined above (C)₁～C₆Alkyl) -O-N ═ (C)₁～C₆Alkyl) groups, for example, mention may be made of: 1- (methoxyimino) ethyl, 2- (methoxyimino) ethyl, 1- (methoxyimino) propyl, 2- (methoxyimino) propyl, 3- (methoxyimino) propyl, 1- (ethoxyimino) ethyl, 2- (ethoxyimino) ethylA group such as 1- (ethoxyimino) propyl group, 2- (ethoxyimino) propyl group, 3- (ethoxyimino) propyl group, 1- (isopropoxyimino) ethyl group, or 2- (isopropoxyimino) ethyl group.

In the present invention, "C" is not particularly limited₁～C₆Halogenoalkyloxyimino group C₁～C₆Alkyl "denotes an alkyl moiety as defined above (C)₁～C₆Haloalkyl) -O-N ═ (C)₁～C₆Alkyl) groups, for example, mention may be made of: 2- (2, 2-difluoroethoxyimino) ethyl group, 2- (2,2, 2-trifluoroethoxyimino) propyl group, or 3- (2,2, 2-trifluoroethoxyimino) propyl group.

In the present invention, "C" is not particularly limited₇～C₁₃Examples of the "aralkyl group" include a benzyl group, a 1-phenethyl group, a 2-phenylpropyl group, a (naphthyl-1-yl) methyl group, a (naphthyl-2-yl) methyl group and the like.

In the present invention, "cyano group C" is not particularly limited₁～C₆Alkyl "denotes (cyano) - (C) with the alkyl moiety as defined above₁～C₆Alkyl) groups, for example, mention may be made of: cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 3-cyanopropyl, 2-cyanopropan-2-yl, 1-cyanobutyl, 4-cyanobutyl, 5-cyanopentyl, or 6-cyanohexyl.

In the present invention, "cyano group C" is not particularly limited₃～C₆Cycloalkyl "means that the cycloalkyl moiety is (cyano) - (C) as defined above₃～C₆Cycloalkyl) groups, for example, mention may be made of: 1-cyanocyclopropyl, 2-cyanocyclopropyl, 1-cyanocyclobutyl, 3-cyanocyclobutyl, 1-cyanocyclopentyl and the like.

In the present invention, "C" is not particularly limited₁～C₆Alkylsulfonyloxy "means an alkyl moiety as defined above (C)₁～C₆Alkyl) -S (═ O)₂Examples of the-O-group include a methylsulfonyloxy group, an ethylsulfonyloxy group and an isopropylsulfonyl groupAcyloxy, and the like.

In the present invention, "C" is not particularly limited₁～C₆Alkylcarbonyl "denotes an alkyl moiety as defined above (C)₁～C₆Alkyl) -C (═ O) -yl, for example, there may be mentioned: acetyl, propionyl, 2-methylpropionyl, 2-dimethylpropionyl, butyryl, 2-methylbutyryl, 3-methylbutyryl, 2-ethylbutyryl, 2-dimethylbutyryl, 2, 3-dimethylbutyryl, 3-dimethylbutyryl, valeryl, 2-methylpentanoyl, 3-methylpentanoyl, 4-methylpentanoyl or hexanoyl.

In the present invention, "C" is not particularly limited₁～C₆Alkoxy radical C₁～C₆Alkylcarbonyl "denotes an alkyl moiety as defined above (C)₁～C₆Alkyl) -O- (C₁～C₆Alkyl) -C (═ O) -yl, for example, there may be mentioned: a methoxyacetyl group, an ethoxyacetyl group, a propoxyacetyl group, an isopropoxyacetyl group, a butoxyacetyl group, a 2-methoxypropionyl group, a 3-methoxypropionyl group, a 2-ethoxypropionyl group, a 3-ethoxypropionyl group, a 2-methoxybutyryl group, a 4-methoxybutyryl group, a 2-methoxyvaleryl group, or a 5-methoxyvaleryl group.

In the present invention, "C" is not particularly limited₃～C₆Cycloalkylcarbonyl "means that the cycloalkyl moiety is as defined above (C)₃～C₆Cycloalkyl) -C (═ O) -yl, examples of which include: cyclopropanecarbonyl, cyclobutanecarbonyl, cyclopentanecarbonyl, cyclohexanecarbonyl, or the like.

In the present invention, "C₁～C₆Alkoxycarbonyl "means an alkoxy moiety as defined above (C)₁～C₆Alkoxy) -C (═ O) -yl, for example, there may be mentioned: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, n-pentyloxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 1-ethylpropoxycarbonyl, 1-dimethylpropoxycarbonylA group such as 1, 2-dimethylpropoxycarbonyl group or 2, 2-dimethylpropoxycarbonyl group.

In the present invention, "C" is not particularly limited₇～C₁₃Aralkylcarbonyl "denotes an aralkyl moiety as defined above (C)₇～C₁₃Aralkyl) -C (═ O) -yl, for example, mention may be made of: phenylacetyl, 1-phenylpropionyl or 2-phenylpropionyl, and the like.

In the present invention, "(C) unless otherwise specified₁～C₆Alkyl) thiocarbonyl "means that the alkyl moiety is (C) as defined above₁～C₆Alkyl) -C (═ S) -yl, for example, there may be mentioned: methylthiocarbonyl, ethylthiocarbonyl, n-propylthiocarbonyl, isopropylthiocarbonyl, n-butylthiocarbonyl, isobutylthiocarbonyl, sec-butylthiocarbonyl, tert-butylthiocarbonyl or n-pentylthiocarbonyl and the like.

In the present invention, "(C) unless otherwise specified₁～C₆Alkoxy) thiocarbonyl "means that the alkyl moiety is (C) as defined above₁～C₆Alkyl) -O-C (═ S) -yl, for example, there may be mentioned: a methoxythiocarbonyl group, an ethoxythiocarbonyl group, a n-propoxylthiocarbonyl group, an isopropoxythiocarbonyl group, a n-butoxythiocarbonyl group, an isobutoxythiocarbonyl group, a sec-butoxythiocarbonyl group, a tert-butoxythiocarbonyl group, a n-pentoxythiocarbonyl group, a 1-methylbutoxythiocarbonyl group, a 2-methylbutoxythiocarbonyl group, a 3-methylbutoxythiocarbonyl group, a 1-ethylpropyloxythiocarbonyl group, a 1, 1-dimethylpropyloxythiocarbonyl group, a 1, 2-dimethylpropyloxythiocarbonyl group, a 2, 2-dimethylpropyloxythiocarbonyl group, or the like.

In the present invention, "C₃～C₆Cycloalkyl radical C₁～C₆Alkylcarbonyl "denotes a cycloalkyl moiety as defined above (C)₃～C₆Cycloalkyl radical C₁～C₆Alkyl) -C (═ O) -yl, for example, there may be mentioned: 2-cyclopropylacetyl, 2-cyclobutylacetyl, 2-cyclopentylacetyl, 2-cyclohexylacetyl, 2-cyclopropylpropionyl or 2-cyclopropylbutyryl.

In the present invention, "C" is not particularly limited₁～C₆Haloalkylthio "means an alkyl halide moiety as defined above (C)₁～C₆Haloalkyl) -S-groups, examples of which include: fluoromethylthio, difluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2, 2-trifluoroethylthio, pentafluoroethylthio, 2,2, 2-trichloroethylthio, 3,3, 3-trifluoropropylthio, 1,1,2,3,3, 3-hexafluoropropylthio, heptafluoropropylthio, 1,1,1,3,3, 3-hexafluoropropan-2-ylthio, heptafluoropropan-2-ylthio or 4,4, 4-trifluorobutylthio, and the like.

In the present invention, "C" is not particularly limited₁～C₆Haloalkylsulfinyl "means an alkyl halide moiety as defined above (C)₁～C₆Examples of haloalkyl) -S (═ O) -groups include: difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2, 2-trifluoroethylsulfinyl, 2, 2-trichloroethylsulfinyl, pentafluoroethylsulfinyl, 3,3, 3-trifluoropropylsulfinyl, heptafluoropropylsulfinyl or heptafluoro-2-propylsulfinyl, and the like.

In the present invention, "C" is not particularly limited₁～C₆Haloalkylsulfonyl "means an alkyl halide moiety as defined above (C)₁～C₆Haloalkyl) -S (═ O)₂Examples of the "group" include: difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2, 2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, 3,3, 3-trifluoropropylsulfonyl, heptafluoropropylsulfonyl, heptafluoro-2-propylsulfonyl and the like.

In the present invention, agriculturally acceptable salts mean salts with metals or organic bases or salts with inorganic acids or organic acids, in the case where a hydroxyl group, a carboxyl group, an amino group, or the like is present in the structure of the compound of the present invention represented by the general formula [ I ] or [ II ], or on the nitrogen atom of the pyridine ring; examples of the metal include alkali metals such as sodium and potassium, and alkaline earth metals such as magnesium and calcium; examples of the organic base include triethylamine, diisopropylamine, and the like; examples of the inorganic acid include phosphoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, boric acid, and sulfuric acid; examples of the organic acid include formic acid, acetic acid, lactic acid, ascorbic acid, succinic acid, fumaric acid, maleic acid, oxalic acid, citric acid, benzoic acid, salicylic acid, tartaric acid, methanesulfonic acid, 4-toluenesulfonic acid, trifluoromethanesulfonic acid, and the like.

Next, representative examples of compounds contained in the pyrazole-3-carboxylic acid amide derivative of the present invention represented by the general formula [ I ] are shown in tables 1 to 93, and representative examples of compounds contained in the pyrazole-3-carboxylic acid derivative of the present invention represented by the general formula [ II ] are shown in tables 94 to 149. However, the compounds contained in the derivatives of the present invention are not limited thereto. The compound numbers in the tables can be referred to the following descriptions.

In the compounds contained in the pyrazole-3-carboxylic acid amide derivative or pyrazole-3-carboxylic acid derivative of the present invention, E-type and Z-type geometric isomers may exist depending on the kind of the substituent, and the present invention includes these E-type, Z-type, or a mixture containing the E-type and Z-type in any ratio. In addition, the compounds contained in the present invention may have optical isomers due to the presence of 1 or 2 or more asymmetric carbon atoms and asymmetric sulfur atoms, and the present invention includes all optically active forms, racemates or diastereoisomers.

The following symbols in the tables of the present specification represent the corresponding groups described below, respectively.

CF₃: trifluoromethyl radical

(4-CF₃) Ph: 4-trifluoromethylphenyl group

(2-F-4-CF₃) Ph: 2-fluoro-4-trifluoromethylphenyl

[ Table 1]

[ Table 2]

[ Table 3]

[ Table 4]

[ Table 5]

[ Table 6]

[ Table 7]

[ Table 8]

[ Table 9]

[ Table 10]

[ Table 11]

[ Table 12]

[ Table 13]

[ Table 14]

[ Table 15]

[ Table 16]

[ Table 17]

[ Table 18]

[ Table 19]

[ Table 20]

[ Table 21]

[ Table 22]

[ Table 23]

[ Table 24]

[ Table 25]

[ Table 26]

[ Table 27]

[ Table 28]

[ Table 29]

[ Table 30]

[ Table 31]

[ Table 32]

[ Table 33]

[ Table 34]

[ Table 35]

[ Table 36]

[ Table 37]

[ Table 38]

[ Table 39]

[ Table 40]

[ Table 41]

[ Table 42]

[ Table 43]

[ Table 44]

[ Table 45]

[ Table 46]

[ Table 47]

[ Table 48]

[ Table 49]

[ Table 50]

[ Table 51]

[ Table 52]

[ Table 53]

[ Table 54]

[ Table 55]

[ Table 56]

[ Table 57]

[ Table 58]

[ Table 59]

[ Table 60]

[ Table 61]

[ Table 62]

[ Table 63]

[ Table 64]

[ Table 65]

[ Table 66]

[ Table 67]

[ Table 68]

[ Table 69]

[ Table 70]

[ Table 71]

[ Table 72]

[ Table 73]

[ Table 74]

[ Table 75]

[ Table 76]

[ Table 77]

[ Table 78]

[ Table 79]

[ Table 80]

[ Table 81]

[ Table 82]

[ Table 83]

[ Table 84]

[ Table 85]

[ Table 86]

[ Table 87]

[ Table 88]

[ Table 89]

[ Table 90]

[ Table 91]

[ Table 92]

[ Table 93]

[ Table 94]

[ Table 95]

[ Table 96]

[ Table 97]

[ Table 98]

[ Table 99]

[ Table 100]

[ watch 101]

[ Table 102]

[ Table 103]

[ Table 104]

[ Table 105]

[ Table 106]

[ Table 107]

[ Table 108]

[ Table 109]

[ Table 110]

[ Table 111]

[ Table 112]

[ Table 113]

[ Table 114]

[ Table 115]

[ Table 116]

[ Table 117]

[ Table 118]

[ Table 119]

[ Table 120]

[ Table 121]

[ Table 122]

[ Table 123]

[ Table 124]

[ Table 125]

[ Table 126]

[ Table 127]

[ Table 128]

[ Table 129]

[ Table 130]

[ watch 131]

[ Table 132]

[ Table 133]

[ Table 134]

[ Table 135]

[ Table 136]

[ Table 137]

[ Table 138]

[ Table 139]

[ Table 140]

[ Table 141]

[ watch 142]

[ Table 143]

[ Table 144]

[ Table 145]

[ Table 146]

[ Table 147]

[ Table 148]

[ Table 149]

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

< preparation method 1>

Among the compounds of the present invention, the compounds represented by the general formula [ V ] can be prepared, for example, according to the following methods.

[ chemical formula 3]

(in the formula, R¹⁷Is represented by C₁～C₆Alkyl radical, R¹、R²、R³、R⁴、R⁵、R⁶、R⁷And R⁸The same as above. )

That is, the compound represented by the general formula [ V ] can be produced by reacting the compound represented by the general formula [ III ] with the compound represented by the general formula [ IV ] in an appropriate solvent in the presence or absence of an appropriate base.

The amount of the compound [ IV ] used in the reaction is usually appropriately selected from the range of 1 to 500 moles, and preferably 1.0 to 300 moles, based on 1 mole of the compound [ III ].

Examples of the solvent that can be used in the present reaction include: ethers such as diethyl ether, tetrahydrofuran, methyl tert-butyl ether, and 1, 4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1, 2-dichloroethane; aprotic polar solvents such as N, N-dimethylformamide, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, and cyclobutyl sulfone; alcohols such as methanol, ethanol, and 2-propanol; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane and the like; pyridines such as pyridine and picoline; water, or a mixed solvent thereof, and the like. The amount of the solvent used is 0.1 to 500 liters, preferably 0.2 to 50 liters, based on 1 mole of the compound [ III ].

Examples of the base usable in the present reaction include: hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide; carbonates of alkali metals such as sodium carbonate and potassium carbonate; inorganic bases such as alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydrides such as sodium hydride and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; or organic bases such as triethylamine, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine and 1, 8-diazabicyclo [5.4.0] -7-undecene. The amount of the base to be used may be appropriately selected from the range of 0 to 5 mol, and preferably 0 to 1.2 mol, based on 1 mol of the compound [ II ].

The reaction temperature of the present reaction can be selected from any temperature range of from-30 ℃ to the reflux temperature of the reaction system, and is preferably in the range of from 0 ℃ to 150 ℃.

The reaction time of the present reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount, and the like, but is usually 10 minutes to 24 hours.

After the reaction is completed, the compound [ V ] can be isolated by adding water to the reaction mixture, and extracting with an organic solvent, followed by concentration or the like. The isolated compound [ V ] can be further purified by column chromatography, recrystallization, or the like, as necessary.

< preparation method 2>

Among the compounds of the present invention, the compounds represented by the general formula [ VI ] can be prepared, for example, according to the following methods.

[ chemical formula 4]

(in the formula, R¹、R²、R³、R⁴、R⁵、R⁶And R¹⁷The same as above. )

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

Examples of the base usable in the present reaction include: hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide, lithium hydroxide, and barium hydroxide; carbonates of alkali metals such as sodium carbonate and potassium carbonate; and inorganic bases such as alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate. The amount of the base to be used may be appropriately selected from the range of 0.1 to 50 mol, and preferably 0.5 to 20 mol, based on 1 mol of the compound [ III ].

Examples of the acid usable in the present reaction include: inorganic acids such as hydrochloric acid, hydrobromic acid and sulfuric acid, and carboxylic acids such as acetic acid and trifluoroacetic acid. The amount of the acid to be used may be appropriately selected from the range of 1 to 1000 moles, preferably 1 to 100 moles, based on 1 mole of the compound [ III ].

Examples of the solvent that can be used in the present reaction include: ethers such as diethyl ether, tetrahydrofuran, methyl tert-butyl ether, and 1, 4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N, N-dimethylformamide, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, and cyclobutyl sulfone; alcohols such as methanol, ethanol, and 2-propanol; nitriles such as acetonitrile and propionitrile; ketones such as acetone and methyl ethyl ketone; water, or a mixed solvent thereof, and the like. The amount of the solvent used may be 0.1 to 500 liters, and preferably 0.3 to 30 liters, based on 1 mole of the compound [ III ].

The reaction temperature in the present reaction can be selected from any temperature range of from-30 ℃ to the reflux temperature of the reaction system, and the reaction is preferably carried out in the range of from 0 ℃ to 150 ℃.

The reaction time of the present reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount, and the like, but is usually 10 minutes to 24 hours.

After the completion of the reaction, the compound [ VI ] can be isolated by adding the reaction mixture to water to neutralize it, collecting the precipitated solid by filtration, or extracting it with an organic solvent and then concentrating it. The isolated compound [ VI ] can be further purified by column chromatography, recrystallization, or the like, as required.

< preparation method 3>

Among the compounds of the present invention, the compounds represented by the general formula [ V ] can also be produced, for example, according to the following methods.

[ chemical formula 5]

(in the formula, X¹Represents a halogen atom, R¹、R²、R³、R⁴、R⁵、R⁶、R⁷And R⁸The same as above. )

That is, the compound represented by the general formula [ V ] can be produced by the following steps: (step 1) producing the compound [ VI ] into the compound [ VII ] using an acid halogenating agent in a suitable solvent in the presence or absence of a suitable catalyst; then, (step 2) with the compound [ IV ] in an appropriate solvent in the presence or absence of an appropriate base.

(step 1)

Examples of the acid halide usable in the present reaction include: thionyl chloride, oxalyl chloride or phosphorus oxychloride and the like. The amount of the acid halide used may be appropriately selected from the range of 0.1 to 30 moles, preferably 0.5 to 6 moles, based on 1 mole of the compound [ VI ].

Examples of the catalyst that can be used in the present reaction include: n, N-dimethylformamide, and the like. The amount of the catalyst to be used may be appropriately selected from the range of 0.01 to 1 mol, and preferably 0.01 to 0.1 mol, based on 1 mol of the compound [ VI ].

Examples of the solvent that can be used in the present reaction include: ethers such as diethyl ether, tetrahydrofuran, and 1, 4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1, 2-dichloroethane; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate, butyl acetate, ethyl propionate, etc.; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane and the like; or a mixed solvent thereof. The amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 10 liters, based on 1 mole of the compound [ VI ].

The reaction time of the present reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount, and the like, but is usually 10 minutes to 24 hours.

After completion of the reaction, the compound [ VII ] can be isolated by a procedure such as concentration.

(step 2)

The amount of the compound [ IV ] used in the reaction is usually appropriately selected from the range of 1 to 500 moles, preferably 1.0 to 300 moles, based on 1 mole of the compound [ VI ].

The base, solvent, reaction temperature and reaction time usable in the present reaction are the same as in the above-mentioned production method 1.

After the completion of the reaction, the compound [ V ] can be isolated by adding the reaction mixture to water, collecting the precipitated solid by filtration, or by extracting with an organic solvent and then concentrating. The isolated compound [ V ] can be further purified by column chromatography, recrystallization, or the like, as necessary.

< preparation method 4>

Among the compounds of the present invention, the compounds represented by the general formula [ V ] can also be produced, for example, according to the following methods.

[ chemical formula 6]

(in the formula, R¹、R²、R³、R⁴、R⁵、R⁶、R⁷And R⁸The same as above. )

That is, the compound represented by the general formula [ V ] can be produced by reacting the compound [ VI ] with the compound [ IV ] in an appropriate solvent in the presence or absence of an appropriate condensing agent and an appropriate base.

The amount of the compound [ IV ] used in the reaction may be appropriately selected from the range of 1 to 3 moles, preferably 1.0 to 1.2 moles, based on 1 mole of the compound [ VI ].

Examples of the condensing agent that can be used in the present reaction include: 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, N ' -dicyclohexylcarbodiimide, N ' -diisopropylcarbodiimide, N ' -carbonyldiimidazole, 4- (4, 6-dimethoxy-1, 3, 5-triazin-2-yl) -4-methylchloromorpholine, 1H-benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate, { [ (1-cyano-2-ethoxy-2-oxoethylidene) amino ] oxy } -4-morpholinylmethylene } dimethylammonium hexafluorophosphate, sodium chloride, potassium chloride, sodium chloride, O- (7-azabenzotriazol-1-yl) -N, N, N ', N' -tetramethyluronium hexafluorophosphate, and the like. The amount of the condensing agent to be used may be appropriately selected from the range of 1 to 3 moles, preferably 1.0 to 1.2 moles, based on 1 mole of the compound [ VI ].

When a base is used in the present reaction, examples of the base that can be used include organic bases such as triethylamine, 4-methylmorpholine, diisopropylethylamine, 1, 8-diazabicyclo [5.4.0] -7-undecene, pyridine, 4-N, N-dimethylaminopyridine and 2, 6-dimethylpyridine. The amount of the base to be used may be appropriately selected from the range of 0 to 5 mol, and preferably 0.1 to 2.2 mol, based on 1 mol of the compound [ VI ].

Examples of the solvent that can be used in the present reaction include: halogenated hydrocarbons such as dichloromethane, chloroform, and 1, 2-dichloroethane; hydrocarbons such as hexane and heptane; esters such as ethyl acetate; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N, N-dimethylformamide, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, and cyclobutyl sulfone; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1, 4-dioxane; or a mixed solvent thereof. The amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 50 liters, based on 1 mole of the compound [ VI ].

The present invention may be carried out in the presence of a catalyst as required, and examples of the catalyst include: 4- (N, N-dimethyl) aminopyridine, 4-hydroxybenzotriazole, and the like. The amount of the catalyst to be used may be appropriately selected from the range of 0.001 to 1 mol, and preferably 0.01 to 0.1 mol, based on 1 mol of the compound [ VI ].

The reaction temperature in the present reaction can be selected from any temperature range from-20 ℃ to the reflux temperature of the reaction system, and the reaction is preferably carried out in the range of 0 ℃ to 80 ℃.

The reaction time of the present reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount, and the like, but is usually 1 minute to 48 hours.

After the reaction is completed, the compound [ V ] can be isolated by adding the reaction mixture to water, extracting with an organic solvent, and then concentrating. The isolated compound [ V ] can be further purified by column chromatography, recrystallization, or the like, as necessary.

< preparation method 5>

Among the compounds of the present invention, the compound represented by the general formula [ IX ] can be prepared, for example, by using the compound represented by the general formula [ VIII ] and according to the following method.

[ chemical formula 7]

(in the formula, R¹⁸Is represented by OR¹⁷Radicals or NR⁷R⁸A group; r¹⁹Represents unsubstituted or substituted by R⁹A substituted benzyl group; r¹、R²、R³、R⁴、R⁵And R⁹The same as above. )

That is, the compound represented by the general formula [ IX ] can be produced by subjecting the compound [ VIII ] to a hydrogenolysis reaction in an appropriate solvent in a hydrogen atmosphere in the presence of an appropriate catalyst.

Examples of the catalyst used in the present reaction include: platinum, Raney nickel, platinum black, palladium-carbon, palladium black, palladium hydroxide-carbon, platinum oxide, and the like. The amount of the catalyst to be used may be appropriately selected from the range of 0.01 to 1 mol, and preferably 0.01 to 0.1 mol, based on 1 mol of the compound [ VIII ].

Examples of the solvent that can be used in the present reaction include: ethers such as diethyl ether, tetrahydrofuran, and 1, 4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N, N-dimethylformamide, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, and cyclobutyl sulfone; alcohols such as methanol, ethanol, 2-propanol, and methylcellosolve; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane and the like; ketones such as acetone and 2-butanone; esters such as ethyl acetate, butyl acetate, ethyl propionate, etc.; water, acetic acid, or a mixed solvent thereof. The amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 30 liters, based on 1 mole of the compound [ VIII ].

The reaction temperature in the present reaction can be selected from any temperature range from 0 ℃ to the reflux temperature of the reaction system, and the reaction is preferably carried out in the range of 0 ℃ to 150 ℃.

The reaction time of the present reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount, and the like, but is usually 10 minutes to 24 hours.

After completion of the reaction, the compound [ IX ] can be isolated by adding the reaction mixture to water, extracting with an organic solvent, and then concentrating. Alternatively, the compound [ IX ] can also be isolated by filtering insoluble materials from the reaction mixture and then concentrating the solvent. The isolated compound [ IX ] may be further purified by column chromatography, recrystallization, or the like, as necessary.

< preparation method 6>

Among the compounds of the present invention, the compound represented by the general formula [ XII ] can be produced, for example, by using the compound represented by the general formula [ IX ] and according to the following method.

[ chemical formula 8]

(in the formula, R²⁰Represents a fluorine atom, C₁～C₆Alkoxy radical, C₁～C₆Haloalkyl or C₁～C₆A haloalkoxy group; r¹、R²、R³、R⁴、R⁵、R⁶And R¹⁸The same as above; x²Represents a halogen atom, C₁～C₆Alkylsulfonyloxy, trifluoromethylsulfonyloxy, nonafluorobutylsulfonyloxy, phenylsulfonyloxy, 4-toluenesulfonyloxy, C₁～C₆Alkylsulfonyl, phenylsulfonyl or 4-toluenesulfonyl. )

That is, the compound represented by the general formula [ XII ] can be produced by reacting the compound [ IX ] with the compound [ X ] or the compound [ XI ] in an appropriate solvent in the presence or absence of an appropriate base.

The amount of the compound [ X ] or the compound [ XI ] used in the reaction is appropriately selected from the range of 1 to 5 moles, preferably 1.0 to 1.2 moles, based on 1 mole of the compound [ IX ].

Examples of the solvent that can be used in the present reaction include: ethers such as diethyl ether, tetrahydrofuran, and 1, 4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N, N-dimethylformamide, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, and cyclobutyl sulfone; alcohols such as methanol, ethanol, 2-propanol, and methylcellosolve; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane and the like; pyridines such as pyridine and picoline; tertiary amines such as triethylamine and tributylamine; water, or a mixed solvent thereof, and the like. The amount of the solvent used is 0.1 to 300 liters, preferably 0.3 to 50 liters, based on 1 mole of the compound [ IX ].

Examples of the base usable in the present reaction include: hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide; carbonates of alkali metals such as sodium carbonate and potassium carbonate; inorganic bases such as alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydrides such as sodium hydride and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; or organic bases such as triethylamine, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine and 1, 8-diazabicyclo [5.4.0] -7-undecene. The amount of the base to be used may be appropriately selected from the range of 1 to 5 moles, preferably 1.0 to 1.2 moles, based on 1 mole of the compound [ IX ]. Further, organic bases such as triethylamine and pyridine can be used as the solvent.

The reaction temperature in the present reaction can be selected from any temperature range from-70 ℃ to the reflux temperature of the reaction system, and the reaction is preferably carried out in the range of 0 ℃ to 150 ℃.

The reaction time of the present reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount, and the like, but is usually 10 minutes to 24 hours.

After the reaction is completed, the compound [ XII ] can be isolated by adding the reaction mixture to water, extracting with an organic solvent, and then concentrating. The isolated compound [ XII ] can be further purified by column chromatography, recrystallization, or the like as necessary.

< preparation method 7>

[ chemical formula 9]

(in the formula, R¹、R²、R³、R⁴、R⁵、R⁶And R¹⁸The same as above. )

That is, the compound represented by the general formula [ XII ] can be prepared by reacting the compound [ IX ] with the compound [ XIII ] in an appropriate solvent in the presence of a tri-substituted phosphine and an azodicarboxylic acid derivative, or in the presence of a phosphane reagent.

The amount of the compound [ XIII ] used in the reaction may be appropriately selected from the range of 1.0 to 5.0 moles, preferably 1.0 to 2.0 moles, based on 1 mole of the compound [ IX ].

Examples of the solvent that can be used in the present reaction include: ethers such as diethyl ether, tetrahydrofuran, and 1, 4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N, N-dimethylformamide, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, and cyclobutyl sulfone; nitriles such as acetonitrile and propionitrile; halogenated hydrocarbons such as dichloromethane, chloroform, and 1, 2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane and the like; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; water, or a mixed solvent thereof, and the like. The amount of the solvent used is 0.1 to 300 liters, preferably 0.3 to 50 liters, based on 1 mole of the compound [ IX ].

Examples of trisubstituted phosphines that may be used in the present reaction include: triphenylphosphine, tributylphosphine, trimethylphosphine, and the like. The amount of the trisubstituted phosphine to be used may be appropriately selected from the range of 1.0 to 5.0 moles, preferably 1.0 to 3.0 moles, based on 1 mole of the compound [ IX ].

Examples of the azodicarboxylic acid derivative which can be used in the present reaction include: diethyl azodicarboxylate, diisopropyl azodicarboxylate, dimethoxyethyl azodicarboxylate, N, N, N ', N' -tetramethylazodicarboxylate, and the like. The amount of the azodicarboxylic acid derivative to be used may be appropriately selected from the range of 1.0 to 5.0 moles, and preferably 1.0 to 2.0 moles, based on 1 mole of the compound [ IX ].

Examples of the phosphine reagent which can be used in the present reaction include: cyanomethylene trimethylphospholane, cyanomethylene tributylphosphane, and the like. The amount of the phosphane to be used may be appropriately selected from the range of 1.0 to 5.0 moles, and preferably 1.0 to 2.0 moles, based on 1 mole of the compound [ IX ]. The reaction temperature in the present reaction can be selected from any temperature range of from-30 ℃ to the reflux temperature of the reaction system, and the reaction is preferably carried out in the range of from 0 ℃ to 150 ℃.

The reaction time of the present reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount, and the like, but is usually 10 minutes to 24 hours.

After the reaction is completed, the compound [ XII ] can be isolated by adding the reaction mixture to water, extracting with an organic solvent, and then concentrating. Alternatively, the compound [ XII ] can also be isolated by concentrating the solvent from the reaction mixture. The isolated compound [ XII ] can be further purified by column chromatography, recrystallization, or the like as necessary.

< preparation method 8>

Among the compounds of the present invention, the compound represented by the general formula [ V ] can be prepared, for example, by using the compound represented by the general formula [ XIV ] and according to the following method.

[ chemical formula 10]

(in the formula, X³Represents a halogen atom, C₁～C₆Alkylsulfonyloxy, trifluoromethylsulfonyloxy, nonafluorobutylsulfonyloxy, phenylSulfonyloxy, 4-tosyloxy, C₁～C₆Alkylsulfonyl, phenylsulfonyl or 4-toluenesulfonyl; r¹、R²、R³、R⁴、R⁵、R⁶、R⁷And R⁸The same as above. )

That is, the compound represented by the general formula [ V ] can be produced by reacting the compound [ XIV ] with the compound [ XV ] or the compound [ XVI ] in an appropriate solvent in the presence or absence of an appropriate base.

The amount of the compound [ XV ] or the compound [ XVI ] used in the reaction may be appropriately selected from the range of 1 to 10 moles, preferably 1.0 to 5.0 moles, based on 1 mole of the compound [ XIV ].

Examples of the solvent that can be used in the present reaction include: ethers such as diethyl ether, tetrahydrofuran, and 1, 4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N, N-dimethylformamide, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, and cyclobutyl sulfone; alcohols such as methanol, ethanol, 2-propanol, and methylcellosolve; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane and the like; pyridines such as pyridine and picoline; water, or a mixed solvent thereof, and the like. The amount of the solvent used is 0.1 to 300 liters, preferably 0.3 to 50 liters, based on 1 mole of the compound [ XIV ].

Examples of the base usable in the present reaction include: hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; hydroxides of alkaline earth metals such as calcium hydroxide and magnesium hydroxide; carbonates of alkali metals such as sodium carbonate and potassium carbonate; inorganic bases such as alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; metal hydrides such as sodium hydride and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; or organic bases such as triethylamine, N-dimethylaniline, pyridine, 4-N, N-dimethylaminopyridine and 1, 8-diazabicyclo [5.4.0] -7-undecene. The amount of the base to be used may be appropriately selected from the range of 1 to 10 moles, preferably 1 to 6 moles, based on 1 mole of the compound [ XIV ]. Further, organic bases such as triethylamine and pyridine can be used as the solvent.

The reaction may be carried out in the presence of a catalyst as required, and examples of the catalyst include: pyridine, 4- (N, N-dimethyl) aminopyridine, 4-pyrrolidinylpyridine, and the like. The amount of the catalyst to be used may be appropriately selected from the range of 0.001 to 1 mol, and preferably 0.01 to 0.1 mol, based on 1 mol of the compound [ XIV ].

The reaction time of the present reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount, and the like, but is usually 10 minutes to 24 hours.

< preparation method 9>

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

[ chemical formula 11]

(in the formula, R¹、R²、R³、R⁴、R⁵、R⁶、R⁷And R⁸The same as above. )

That is, the compound represented by the general formula [ XVII ] can be prepared by reacting the compound [ V ] with an appropriate sulfurizing agent.

Examples of the solvent that can be used in the present reaction include: ethers such as diethyl ether, tetrahydrofuran, and 1, 4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as dimethyl sulfoxide and cyclobutyl sulfone; halogenated hydrocarbons such as dichloromethane, chloroform, and 1, 2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane and the like; water, or a mixed solvent thereof, and the like. The amount of the solvent used is 0.1 to 300 liters, preferably 0.3 to 50 liters, based on 1 mole of the compound [ V ].

Examples of the sulfiding agent that can be used in the present reaction include: phosphorus pentasulfide, Lawesson's reagent, and the like. The amount of the vulcanizing agent to be used may be appropriately selected from the range of 0.5 to 30 moles, preferably 0.5 to 5 moles, based on 1 mole of the compound [ V ].

The reaction time of the present reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount, and the like, but is usually 10 minutes to 24 hours.

After the reaction, the compound [ XVII ] can be isolated by adding the reaction mixture to water, extracting with an organic solvent, and then concentrating. Alternatively, the compound [ XVII ] can also be isolated by concentrating the solvent from the reaction mixture. The isolated compound [ XVII ] can be further purified by column chromatography, recrystallization, or the like as necessary.

< preparation method 10>

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

[ chemical formula 12]

(R²¹Represents a hydroxyl group, OR¹⁷Radicals or NR⁷R⁸A group; in the formula, R¹、R²、R³、R⁴、R⁵、R⁶The same as above. ) That is, from the formula [ XIX]The compound represented by (A) can be prepared by reacting a compound [ XVIII ] in an appropriate solvent in the presence or absence of a catalyst]With a suitable oxidizing agent.

Examples of the solvent that can be used in the present reaction include: halogenated hydrocarbons such as dichloromethane, chloroform, 1, 2-dichloroethane, carbon tetrachloride, chlorobenzene, dichlorobenzene, and the like; ethers such as 1, 4-dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, or diethyl ether; amides such as N, N-dimethylacetamide, N-dimethylformamide, and N-methyl-2-pyrrolidone; alcohols such as methanol, ethanol, propanol, isopropanol, butanol, and tert-butanol; ketones such as acetone and 2-butanone; nitriles such as acetonitrile and propionitrile; acetic acid, water or mixtures thereof. The amount of the solvent used is 0.1 to 500 liters, preferably 0.3 to 200 liters, based on 1 mole of the compound [ XVIII ].

Examples of the oxidizing agent that can be used in the present reaction include: organic peroxides such as m-chloroperbenzoic acid, performic acid, and peracetic acid; hydrogen peroxide, potassium permanganate,(registered trademark) (OXONE, trade name of E.I.du Pont, potassium hydrogen peroxymonosulfate content) or sodium periodate. Note that the compound [ XVIII ] is present in an amount of 1 mol]The amount of the oxidizing agent used is 0.5 to 3 moles.

Examples of the catalyst that can be used in the present reaction include sodium tungstate. The amount of the catalyst used is 0.01 to 0.5 mol based on 1 mol of the compound [ XVIII ].

The reaction time of the present reaction varies depending on the reaction temperature, the reaction substrate, the reaction amount, and the like, but is usually 10 minutes to 24 hours.

After the reaction, the compound [ XIX ] can be isolated by adding the reaction mixture to water, extracting with an organic solvent, and then concentrating. Alternatively, the compound [ XIX ] can also be isolated by concentrating the solvent from the reaction mixture. The isolated compound [ XIX ] can be further purified by column chromatography, recrystallization, or the like as necessary.

< method for producing intermediate >

The compound represented by the formula [ XXIII ] can be produced, for example, by using the compound represented by the formula [ XX ] and according to the following method.

[ chemical formula 13]

(in the formula, R¹、R²、R³、R⁴、R⁵、R¹⁷And X¹The same as above. )

That is, the compound represented by the formula [ XXIII ] can be produced by subjecting the compound [ XX ] and the compound [ XXI ] to the Japp-Klingemann reaction to obtain the compound [ XXII ], followed by the cyclization reaction. Further, the compound represented by the general formula [ XXIII ] can be produced according to or by the method described in International publication No. 2012/028332, International publication No. 2014/114649, International publication No. 2016/027790, International publication No. 2016/166250, or U.S. Pat. No. 5,055,482.

The pest control agent of the present invention contains a pyrazole-3-carboxylic acid amide derivative represented by the general formula [ I ] of the present invention or an agriculturally acceptable salt thereof as an active ingredient. The pest control agent of the present invention is typically an insecticide and an acaricide.

The pest control agent of the present invention may contain an additive ingredient (carrier) generally used for pesticide preparations, as necessary. In addition, the pesticidal composition of the present invention may also contain an additional ingredient (carrier) generally used for a pesticidal formulation.

Examples of the additive components include: carriers such as solid carriers and liquid carriers, surfactants, binders and tackifiers, colorants, extenders, spreading agents, antifreeze agents, anti-caking agents, disintegrating agents, decomposition inhibitors, and the like, and preservatives, plant debris, and the like may be used as additional components as necessary. Further, these additives may be used in 1 kind, and 2 or more kinds may be used in combination.

The above-mentioned additive components are explained below.

Examples of the solid carrier include: mineral carriers such as pyrophyllite clay, kaolin clay, silica clay, talc, diatomaceous earth, zeolite, bentonite, acid clay, activated clay, palygorskite, vermiculite, perlite, pumice, white carbon (synthetic silicic acid, synthetic silicate, etc.), titanium dioxide, etc.; plant carriers such as wood powder, corn stalks, walnut shells, fruit kernels, rice hulls, wood chips, wheat bran, soybean meal, powdered cellulose, starch, dextrin, saccharides and the like; inorganic salt carriers such as calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride, and the like; polyethylene, polypropylene, polyvinyl chloride, polyvinyl acetate, ethylene-vinyl acetate copolymer, urea-formaldehyde resin, and the like.

Examples of the liquid carrier include: monohydric alcohols such as methanol, ethanol, propanol, isopropanol, butanol, and cyclohexanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin; polyhydric alcohol derivatives such as propylene glycol ethers; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, and isophorone; ethers such as diethyl ether, dioxane, cellosolve, dipropyl ether, and tetrahydrofuran; aliphatic hydrocarbons such as normal paraffin, naphthene, iso-paraffin, kerosene, and mineral oil; toluene, C₉-C₁₀Aromatic hydrocarbons such as alkylbenzene, xylene, solvent naphtha, alkylnaphthalene, and high-boiling aromatic hydrocarbons; halogenated hydrocarbons such as 1, 2-dichloroethane, chloroform, carbon tetrachloride and the like; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate, and the like; lactones such as γ -butyrolactone; amides such as N, N-dimethylformamide, N-diethylformamide, N-dimethylacetamide, and N-alkylpyrrolidone; second stepNitriles such as nitriles; sulfur compounds such as dimethyl sulfoxide; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, coconut oil, castor oil, etc.; water, and the like.

The surfactant is not particularly limited, but is preferably a surfactant that gels in water or exhibits swelling properties, and examples thereof include: nonionic surfactants such as sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene dialkylphenyl ethers, polyoxyethylene alkylphenyl ether formalin condensates, polyoxyethylene polyoxypropylene block polymers, alkylpolyoxyethylene polypropylene block polymer ethers, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid bisphenylethers, polyalkylene benzylphenyl ethers, polyoxyalkylene styrylphenyl ethers, acetylene glycols, polyoxyalkylene addition acetylene glycols, polyoxyethylene ether silicones, ester silicones, fluorine surfactants, polyoxyethylene castor oils, polyoxyethylene hydrogenated castor oils, and the like; anionic surfactants such as alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkylphenyl ether sulfates, polyoxyethylene styrene phenyl ether sulfates, alkylbenzenesulfonates, lignosulfonates, alkylsulfonic acid succinates, naphthalenesulfonates, alkylnaphthalenesulfonates, salts of formalin condensates of naphthalenesulfonic acids, salts of formalin condensates of alkylnaphthalenesulfonic acids, fatty acid salts, polycarboxylates, N-methyl-fatty acid sarcosinates, resinates, polyoxyethylene alkyl ether phosphates, and polyoxyethylene alkylphenyl ether phosphates; cationic surfactants such as alkylamine salts including laurylamine hydrochloride, octadecylamine hydrochloride, oleylamine hydrochloride, octadecylamine acetate, octadecylaminopropylamine acetate, alkyltrimethylammonium chloride, and alkyldimethylbenzylammonium chloride; and amphoteric surfactants such as betaine type surfactants including dialkyl diaminoethyl betaine and alkyl dimethylbenzyl betaine, and amino acid type surfactants including dialkyl aminoethyl glycine and alkyl dimethylbenzyl glycine.

Examples of the binder and the tackifier include: carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol having an average molecular weight of 6000 to 20000, polyethylene oxide having an average molecular weight of 10 to 500 ten thousand, natural phospholipids (e.g., phosphatidylethanolamine, lecithin, etc.), and the like.

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

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

Examples of the spreading agent include: silicone surfactants, cellulose powders, dextrins, modified starches, polyaminocarboxylic acid chelate compounds, crosslinked polyvinylpyrrolidone, maleic acid and styrenes, methacrylic acid copolymers, half esters of polymers of polyhydric alcohols and dicarboxylic anhydrides, water-soluble salts of polystyrene sulfonic acid, and the like.

Examples of the developing agent include: various surfactants such as sodium dialkylsulfosuccinate, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, and polyoxyethylene fatty acid ester; paraffin wax, terpene, polyamide resin, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, synthetic resin emulsion, and the like.

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

Examples of the anti-blocking agent include: polysaccharides such as starch, alginic acid, mannose, and galactose; polyvinylpyrrolidone, white carbon, ester gum, petroleum resin, etc.

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

Examples of the decomposition preventing agent include: desiccants such as zeolites, quicklime, magnesium oxide; antioxidants such as phenols, amines, sulfur compounds, and phosphoric acids; ultraviolet absorbers such as salicylic acids and benzophenones.

On the other hand, when the additive component is contained in the pest control agent of the present invention, the content ratio thereof may be selected from the range of usually 5 to 95%, preferably 20 to 90%, of carriers such as solid carriers and liquid carriers on a mass basis; the surfactant is usually selected from the range of 0.1% to 30%, preferably 0.5% to 10%; the other additives are selected from the range of 0.1 to 30%, preferably 0.5 to 10%.

The pest control agent of the present invention is used after being prepared into any dosage form such as powder, powder granule, hydration agent, aqueous solvent, granule hydration agent, tablet, large granule, emulsion, oil agent, liquid preparation, aqueous suspension, emulsion, microemulsion, suspoemulsion, trace dispersant, microcapsule, aerosol, bait, paste and the like.

When these preparations are actually used, they may be used as they are, or may be used after diluted with a diluent such as water to a predetermined concentration. The application of the various preparations containing the compound of the present invention or the diluted product thereof can be generally carried out by a commonly used application method, that is, by spraying (e.g., spraying, fogging, atomizing, dusting, granule-scattering, water-surface application, nursery box application, etc.), soil application (e.g., mixing, pouring, etc.), surface application (e.g., coating, powdery coating, covering, etc.), seed treatment (e.g., smearing, powdery coating treatment, etc.), dipping, poison bait, smoke application, etc. In addition, the effective components can be mixed into feed for livestock to feed, and can also prevent and control the generation and development of pests, especially harmful insects in excrement of livestock.

The method for controlling pests of the present invention can be carried out by using the above-mentioned application method and an effective amount of the compound represented by the general formula [ I ] of the present invention or a salt thereof.

The blending ratio (% by mass) of the active ingredient in the pest control agent of the present invention can be appropriately selected as needed. For example, when a powder, a granule, a fine granule or the like is selected, it is usually 0.01 to 20%, preferably 0.05 to 10%; when selecting the granule, the amount is usually 0.1 to 30%, preferably 0.5 to 20%; when a hydrating agent, a granular hydrating agent or the like is selected, it is appropriately selected usually in the range of 1 to 70%, preferably 5 to 50%; when the aqueous solvent, liquid preparation, etc. are selected, it is usually 1 to 95%, preferably 10 to 80% by weight; when an emulsion or the like is selected, it is appropriately selected in the range of usually 5 to 90%, preferably 10 to 80%; when an oil agent or the like is selected, it is selected appropriately in the range of usually 1 to 50%, preferably 5 to 30%; when an aqueous suspension is selected, it is usually 5 to 60%, preferably 10 to 50% by weight; when an emulsion, a microemulsion, a suspoemulsion, or the like is selected, it is usually 5 to 70%, preferably 10 to 60% as appropriate; when tablets, baits, pastes, etc. are selected, they are selected appropriately in the range of usually 1 to 80%, preferably 5 to 50%; when an aerosol is selected, it is usually 0.1 to 50%, preferably 1 to 30% by weight; when an aerosol is selected, it is preferably selected in the range of 0.05 to 20%, preferably 0.1 to 10%.

These formulations may be diluted to an appropriate concentration for spraying, or applied directly.

When the pest control agent of the present invention is used after diluted with a diluent, it is usually applied at an active ingredient concentration of 0.1 to 5000 ppm. The amount of the active ingredient compound to be applied per unit area when the preparation is used as it is 0.1 to 5000g per 1ha area, but is not limited thereto.

It is needless to say that the pest control agent of the present invention is very effective as an active ingredient alone, but may be used in combination with other fertilizers, agricultural chemicals (for example, insecticides, acaricides, nematicides, synergists, bactericides, antivirals, attractants, herbicides, plant growth regulators) and the like as needed, and in this case, the pest control agent may exhibit a further excellent effect.

Next, well-known insecticide, acaricide, nematicide, synergist compounds which can be mixed or used in combination are shown as examples.

Insecticidal active ingredients: flupropathrin (acrifrin), azadirachtin (azadirachtin), azamethiphos (azamethiphos), acyclonapryr, ethylthion (azinphos-ethyl), azinphos-methyl, acequinocyl, acetamiprid (acetamiprid), acetoprol (acetoprole), acephate (acephate), azocyclotin (azocyclotin), abamectin (abamectin), propiconate (afidozopron), alfurana (aflavoraner), sulfadiazine (amidofluset), amitraz (amitraz), gossyparb (alanycarb), aldicarb (aldicarb), allethrin (ethrin) [ d-cis-trans-isomer, isofenthiuron (isoproxyphos-methyl), isofenphos (isofenphos-methyl), isofenproxyfen (isofenphos-methyl), isofenprox (isofenprox-s (isofenphos), isofenprox-methyl), isofenprox (isofenprox), isofenprox-s (isofenprox), isofenprox-s, isofenprox, isofenproxyfen (iso, Methofluthrin (epsilon-momfluorothrin), ivermectin (ivermectin), imicyafos, imidacloprid (imidacloprid), imipramine (imipramrin), indoxacarb (indoxacarb), esfenvalerate (esfenvalerate), ethiofencarb (ethiofencarb), ethiofen (ethion), ethiprole (ethiprole), ethylene dibromide (ethidene dibromide), etoxazole (etoxazole), ethofenprox (etofenprox), ethoprophos (ethoprophos), ethirimos (ethymemfos), emamectin (emamectin), emamectin benzoate (emamectin benzoate), endosulfan (endosulfan), pentothrin (empenthrin), oxzotif, thiofenthion (ethoprofen), thiofenthiocarb (thiofenthiocarb), thiofenthiocarb (ethiofenprox), thiofenthiofenthiocarb (ethiofenprox), thiofenthiocarb (ethiprolyl), thiofenthiocarb (ethion), thiofenthiofenthiocarb (ethiprolyl), thiocarb (ethiofenprox), thiocarb (ethiprolyl), tefuran (thiocarb (ethiofenproxide), thiocarb (thiocarb), thiocarb (thiocarb), thiocarb, Lindane (gamma-BHC), fenoxycarb (xylylcarb), quinalphos (quinalphos), methoprene (kinoprene), chlorfenapyr (chinomethionat), coumaphos (coumaphos), cryolite (cryolite), clothianidin (clothianidin), clofentezine (clofentezine), chromafenozide (chromafenozide), chlorantraniliprole (chlorantraniliprole), phosphorus oxychloride (chlorethoxyfos), chlordane (chloredane), chloropicrin (chlorepicrin), chlorpyrifos (chlorpyrifos-methyl), chlorfenapyrronitrile (chlorenappyr), chlorfenvinphos (chlorpyrifos), fenvinphos (chlorpyrifos), fenpyrad (chlorpyrifos), fenpyraclostrobin (chlorpyrifos), fenpyrad (chlorpyrifos), fenpropathrin), fenpyraclostrobin (chlorpyrifos), chlorpyrifos (chlorpyrifos), chlorpyrifos (chlorpyrifos), chlorpyrifos (chlorpyrifos), chlorpyrifos (chlorpyrifos), chlorpyrifos (, Cycloprothrin, dichlorvos, diclomezotiz, dicofol, dicyclanil, disulfoton, dinotefuran, cyhalodiamide, cyhalothrin, lambda-isomer, cyphenothrin, cyhalothrin, cyfluthrin, urea, cyflutenzu, cyflufenacet, flufenzine, fluflufenzine, cyflufenzine, cyfluzine, cyfluthrin, cyhalothrin, beta-isomer, dithiopyr, cyhalothrin, fluzine, cyhalothrin, cyhalo, Dimethoate (dimethoate), dimefluthrin (dimefluthrin), silafluofen (silaflufen), cyromazine (cyromazine), spinetoram (spinetoram), spinosad (spinosad), spirodiclofen (spirodiclofen), spirotetramat (spirotetramat), sodium sulfophenoxide (sulfofenoron-sodium), flubendiamide (sulfflufenamide), sulfoxaflor (sulfluramid), sulfotep (sulfotep), diazinon (diazinon), thiacloprid (thiacloprid), thiamethoxam (thiamethoxam), thiofentexafen (thiodicarbazine), thiodicarbazine (tetrachlorfenphos), tetramethrin (tetrachlorfenthion), tetramethrin (tetramethrin), tetramethrin (tetramethrin), tetramethrin (tetramethrin), tefluthrin (tefluthrin), teflubenzuron (teflubenzuron), demeton-S-methyl (demeton-S-methyl), temephos (temephos), deltamethrin (deltamethrin), tolfosson (terbufos), tralomethrin (tralomethrin), transfluthrin (transfluthrin), triazamate (triazamate), triazophos (triazophos), triclosan (triclosan), chlorsulfuron (triflumuron), trifluoropyrimidine (triflumzopyrim), methiocarb (trimethacarb), tolanil (tolfenpyr), naled (naled), nicotine (nicotinoide), nitenpyram (nipyrram), nimustine (nemadectin), novaluron (novaluron), Bacillus (novaluinii), Verticillium (Bacillus subtilis), Bacillus thuringiensis (Bacillus thuringiensis) Bacillus subtilis), Bacillus thuringiensis (Bacillus subtilis), Bacillus subtilis (Bacillus subtilis), Bacillus subtilis (Bacillus subtilis, Bacillus subtilis, Bacillus thuringiensis subsp.Israelensis, Bacillus thuringiensis subsp.Kurstaki, Bacillus thuringiensis subsp.Pseudotsukularensis (Bacillus thuringiensis subsp.Tenebrio), Bacillus japonicus (Bacillus popilliae), Bacillus punctatus (Pasteurella), Midamia variegata (vamidothion), Barathon (parathison), Methylparason (athyrison-methyl), Benzyprex (Halfenprox), Chlorfenazid (Halofenozide), Bioallethrin (Biopentenehrin), S-cyclopentenylbioallethrin (Biochrysin S-biothrin), Bifenthiuron (Biofenthiuron), Biofenthiuron (Biofenthiuron), Biofenprox (Biofenthiuron), Bifenthiuron (Biofenthiuron-2-ethyl-2-bifenthrin (Biofenthifluthrin), Bifenthifluthrin (Biofenthifluthrin-methyl-ethyl), Diphenrythrin (Biofenthifluthrin), Diphenthrin-2-methyl-ethyl, Diphenrythrin (Bifenthifluthrin), Diphenrythrin (Bifenthifluthrin), Diphenthrin (Bifenthifluthrin) and the same, Diphenrythrin (Bifenthiflu, Flubutamine (pyruvoside), pyriproxyfen (pymetrozine), pyraclofos (pyraclofos), pyrazoflufen (pyraflufen), pyraflufenapyr (pyrafluprole), pyridaphenthion (pyripyrophyl), pyrifenofos (pyriproxyfen), pyriproxyfen (pyridall), pyrifluquindox (pyrifluquine), pyriproxyfen (pyriproxyfen), pirimicarb (pyrimicarb), pyriminostrobin (pyriminostrobin), pirimiphos (pirimiphos-methyl), pyrethrin (pyriproxyfen), pyriproxyfen (pyriproxyfen), pyrifenoxycarb (pyrifenoxycarb), fenaminofen (fenfenazatron), fenamiphos (pyriproxyfen-methyl), fenphos (pyriproxyfen (fenphos-methyl), fenthion (fenpropathrin), fenpropineb (fenpropineb), fenpropite (fenpropineb (fenpropite), fenpropite (fenpropineb), fenpropite (fenpropite), fenpropite (fenpropicarb-fenpropite (fenpropite), fenpropicarb (fenpropicarb), fenpropicarb-fenpropicarb (fenpropite), fenpropicarb-fenpropite (fenpropicarb), fenpropicarb-fenpropicarb (fenpropite), fenpropicarb), fenpropite (fenpropicarb-fenpropicarb), fenpropicarb-fenpropite (fenpropicarb-fenpropi, Sulfuryl fluoride (sulfurylfluoride), butocarboxim (butroxycarboxim), butoxycarb (butoxycarb), chlorpheniramine (butrofazine), furametpyr (furathiocarb), prallethrin (prallethrin), fluacrypyrim (fluazaindolizine), flufenapyr (fluazuron), diflufenuron (diflufenuron), fluthrin (flufenidone), fluopyram (flupyramide), flufenamide (fluphenamide), sodium fluoroacetate (sodium flufluoroacetate), fluxamide, epoxiconazole (flucycloxuron), flucythrinate (flufenuron), fluthrin (fluthrin), fluflusulfamide (flufenide), flufenim (flufenim), flufenacet (flufenacet), flufenacet (flufenacet), flufenacet (flufenacet), flufenacet (flufenacet), flu, Propargite (propagite), profenofos (profenofos), brofenbendiamide (brofenilide), proffluthrin (profluthrin), triarocarb (propeetamphos), propoxur (propromur), flumetrequine (flometoquin), bromopropylate (bromopyralate), hexythiazox (hexythiazox), hexaflumuron (hexaflumuron), Paecilomyces tenuipes (Paecilomyces tenuipes), Paecilomyces fumonis (Paecilomyces fumonis), flutolyticus (phenothrin), heptenophos (heptenphos), permethrin (permethrin), chloranilothiaz (benclothiaz), benthiamycin (bensultap), bensultap (bendiocarb), bendiocarb (bendiocarb), fentebuconazole (fenthiocarb), fenthiocarb (carboxim), fenthion (fenthiocarb), fenthiuron (bensultap), fenthiocarb (bendiocarb (benoxacarb), fenthiocarb (bendiocarb (carb), fenugine (benoxacarb), fenthion (bendiocarb (benoxacarb), bendiocarb (benoxacarb (bendiocarb (benoxacarb), bendiocarb (bendiocarb), bendiocarb (bendiocarb), bendiocarb, Malathion (malathion), milbemectin (milbemectin), methicillin (mecarbam), methidathion (mecarb), methomyl (methomyl), metaldehyde (metaldehyde), metaflumizone (metaflumizone), methamidophos (methamidophos), metam (metham), methiocarb (methiocarb), methidathion (methidathion), methidathion (methasulfocyanate), methyl bromide (methyl bromide), methoxychloride (methoxychloride), methoxyfenozide (methoxyfenode), methomeththrin (methofluthrin), metofluthrin (methofluthrin), methomyl (methomyl), metoclopramide (methofluthrin), metoclopramide (metoclopramide), tetramethrin (methofluthrin (metoclopramide), tetramethrin (ammonium, metoclopramide), tetramethrin (ammonium, tetramethrin (methabenzuron (ammonium), tetramethrin (ammonium chloride), tetramethrin (methabenzuron (ammonium chloride), tetramethrin (ammonium chloride), tetramethrin), resmethrin (resmethrin), lepimectin (lepimectin), rotenone (rotenone), nuclear polyhedrosis virus inclusion bodies, fenbutatin oxide (fenbutatin oxide), calcium cyanide (calcium cyanide), organotin compounds (organotins), nicotine sulfate (nicotine-sulfate), (Z) -11-tetradecene acetate, (Z) -11-hexadecene aldehyde, (Z) -11-hexadecene acetate, (Z) -9, 12-tetradecene acetate, (Z) -9-tetradecene-1-ol, (Z, E) -9, 11-tetradecene diene acetate, (Z, E) -9, 12-tetradecene diene acetate, 1,1, 1-trichloro-2, 2-bis (4-chlorophenyl) ethane (DDT), 1,3-dichloropropene (1, 3-dichloropropen), 2, 4-dichloro-5- {2- [4- (trifluoromethyl) phenyl ] ethoxy } phenyl 2,2, 2-trifluoroethylsulfoxide (chemical name, CAS registry number: 1472050-04-6), 2, 4-dichloro-5- {2- [4- (trifluoromethyl) phenyl ] ethoxy } phenyl 2,2, 2-trifluoroethyl sulfoxide (chemical name, CAS registry number: 1472052-11-1), 2, 4-dimethyl-5- [6- (trifluoromethylthio) hexyloxy ] phenyl-2, 2, 2-trifluoroethyl sulfoxide (chemical name, CAS registry No.: 1472050-34-2), 2- { 2-fluoro-4-methyl-5- [ (2,2, 2-trifluoroethyl) sulfinyl ] phenoxy } -5- (trifluoromethyl) pyridine (chemical name, CAS registry No.: 1448758-62-0), 3-chloro-2- { 2-fluoro-4-methyl-5- [ (2,2, 2-trifluoroethyl) sulfinyl ] phenoxy } -5- (trifluoromethyl) pyridine (chemical name, CAS registry number: 1448761-28-1), 4, 6-dinitro-O-cresol (DNOC), 4-fluoro-2-methyl-5- (5, 5-dimethylhexyloxy ] phenyl-2, 2, 2-trifluoroethylsulfoxide (chemical name, CAS registry number: 1472047-71-4), Bt proteins (Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Abl), CL900167 (number), NA-85 (number), NI-30 (number), O-diethyl-O- [4- (dimethylaminosulfonyl) phenyl ] -organophosphorus (DSP), O-ethyl-O-4- (nitrophenyl) phenyl phosphorothioate (EPN), RU15525 (number), XMC (XMC), Z-13-eicosen-10-one, N-methyl-5- (5, 5-dimethylhexyloxy) phenyl-2, 2, 2-trifluoroethyl-protein (Bt), Na-, ZXI8901 (numbering).

Next, well-known bactericide or disease-controlling agent compounds which can be mixed or used in combination are exemplified.

And (3) bactericidal active ingredients:

epoxiconazole (azaconazole), acibenzolar-S-methyl (acibenzolar-S-methyl), azoxystrobin (azoxystrobin), trichlamide (anilazine), amisulbactam (amisulbactam), aminopyrifen, ametoctradin (ametoctradin), dimorpholine (aldimorph), isothiavalicarb (isotianil), isopyrazamide (isopyrazam), isoprothiolamide (isothiamidd), isoflucypram (isoflufenoxam), isoprothiolane (isoprothiolane), iprazole (ipconazole), flufenoquin (ipfendazole), fluconazole (iprovalicazole), iprodione (iprodione), imazalil (imazalil), imazalil (octopamil), pyrithiobac (octopamil), pyrimethanil (ethoxyquin (azofamid), pyrimethanil (ethoxyquin), pyrimethanil (ethoxyquin (fosfamil), pyrimethanil (ethoxypyrimethanil (fosfamil), pyrimethanil (ethoxyquin), pyrimethanil (ethoxypyrimethanil (ethoxyquin), pyrimethanil (fosfamil), pyrimethanil (ethoxypyrimethanil), pyrimethanil (pyrimethanil), pyrimethanil (pyrimethanil), pyrimethanil (pyrimethanil), pyri, Enestroburin (enoxastrobin), epoxiconazole (epoxiconazole), organic oils (organic oils), oxadixyl (oxadixyl), oxazizyl (oxazizyl), oxcarbazolyl, oxcarbazepine (oxathiprirol), carboxin (oxacarboxin), sunamin (oxathidine), oxotetracycline (oxotetracycline), oximidazole-fumarate (oxypolyzole), oxoquinonic acid (oxolinic acid), copper dicaprylate (copter dioate), octreone (octilinone), methyluramide (ofaracyne), orysastrobin (orysastrobin), orthophenols (o-phenylphenanol), kasugamycin (kasugamycin), captan (captafol), cyclopropanimide (carproprione), carbenoxadol (fenzim), carboxin (oxoquinate), carboxin (oxazidine), benzoquinone (fenpyroximate), benzoquinone (fenthizone), benzoquinone (fenpyraclostrobin), carbenoxyfen (fenzim), carboxin (oxozone), benzoquinone (fenpyraclostrobin (fenthizone), benzoquinone (fenpyroxim (fenpropiconazole), benzoquinone (fenpyroximate (fenpropiconazole), benzoquinone (fenpyroxim), benzoquinone (fenpropiconazole), benzoquinone (fenchoxycarb (fenpropiconazole), benzoquinone (fenchoxycarb), benzoquinone (fenpropiconazole), benzoquinone (fenchoxycarb), benzoquinone (fenchoxycarb (benzoquinone (fenchoxycarb), benzoquinone (benzoquinone), benzoquinone (fenchoxycarb), benzoquinone (benzoquinone), benzoquinone (benzo, Kresoxim-methyl, clarithromycin (clozylacon), chlozolinate (chlorozoline), tetrachloroisophthalonitrile (chlorothalonil), chlorothalonil (chloroneb), cyazofamid (cyazofamid), diethofencarb (diethofencarb), dichlorfenamid (diclomet), dichlofluanid (dichlofluanid), dibenzazone (diclobutrazol), pyridazone (diclomezine), niclosamide (diclonan), dichlorphenol (dichlorophthalen), dinitrile anthraquinone (dithianon), diniconazole (diniconazole), dacron (diniconazole), diniconazole (diniconazole), zinc (zineb), dinocap (diniconap), pimecron (dimorphone), diphenylamine (diaphorane), xylidine (difenoconazole), difenoconazole (080), difenoconazole (dimethylpyrimethanil), difenoconazole (080-4), difenoconazole (difenoconazole), difenoconazole (difenoconazole), difenoconazole (difenoconazole), difenoconazole (difenoconazole), difenoconazole (dif, Ziram (ziram), silthiopham (silthiopham), streptomycin (streptomycin), spiroxamine (spiroxamine), sedaxane (sedaxane), zoxamine (zoxamine), benzovindiflupyr (solatenol), dazomet (dazomet), albuterol (Talaromyces flavus), tiadinil (tiadinil), thiabendazole (thiabendazole), thiocarbamamide (thiuram), thiophanate (thiophanate-methyl), thifluzamide (thifluzamide), thiram (thiuram), tetrachlor (tecnazene), bisquinate (thifluzamide), thiflutriazole (tetraconazole), prochloraz (tetrachloraz), thifluzamide (trifloxystrobin), thiurazole (tetrachlorfenthiuram), propidium (fenpyroxim), thiuram (tetrachlorfenpyroxim), propiconazole (tetrachlor), triazoxide (tetrachloraz), triazoxide (triazoxide), triazoxide (triazoxide), triazoxide (triazoxide), triazoxide (triaz, Triticonazole (triticonazole), flutriafol (tridemorph), triflumizole (triflumizole), trifloxystrobin (trifloxystrobin), triforine (triforine), tolfenfluranid (tolyfluanid), tolclofos-methyl (tolclofos-methyl), sulfluramid (tolnifanide), tolprocarb (tolprocarb), sodium metam (nabam), natamycin (natamycin), naftifine (naftifine), chloromethylpyridine (nitropyridine), phthalide (nitrofenamic-isoprox), fluoropyrimidine alcohol (nuarimol), copper nonylphenolsulfonate (copperphenanol sulfonate), Bacillus subtilis (Bacillus subtilis) (strain: t713), validamycin (valosin), pyrimethanil (pyrimethanil), pyrimethanil (pyriproxyfen), pyraclostrobin (pyriproxyfen), pyriproxyfen (pyraclostrobin), pyrimethanil (pyraclostrobin (brom), pyrimethanil (pyraclostrobin), pyrimethanil (brom), pyrimethanil (pyraclostrobin), pyrimethanil (pyraclostrobin (brom-p-ethyl), pyrimethanil (pyraclostrobin (brom), pyraclostrobin (pyraclostrobin), pyroflunomide (pyraziflumuron), pyriminostrobin (pyrazophos), pyraproyne, pyraclostrobin (pyrametostrobin), pyriminostrobin (pyriofenone), pyriminostrobin (pyrifenoxaprop-p-ethyl), pyriminostrobin (pyrifenox), pyributicarb (pyributicarb), pyrimethanil (pyrimethanil), pyroquilon (pyroquilon), pyrimethanil (pyribenzofenacin), pyrimethanil (vinclozolin), ferbam (bam), famoxadone (famoxadone), pyrimethanil (phenazine oxide), fenamidone (fenamidone), fenamidoxim (fenamidofen), fenfenamidone (fenfenamidofen), fenpyraclostrobin (fenpyrazone), fenpyraclostrobin (fenpyraclostrobin), pyrimethanil (fenfenamidofen-ethyl), pyrimethanil (fenpyraclostrobin (fenfenamidofen), fenpyrad (fenfenamidofen), fenpyraclostrobin (fenfenamidofen), fenpyrad (fenfenamidofen), fenpyrad (fenpyrazone), fenfenamidofen-fenpyrazone (fenfenamidofen), fenpyrazone (fenpyrad (fenfenamidofen), fenpyrad (fenpyrazone (fenpyrad (fenpyrazone), fenpyrad (, Furametpyr, furocarboxylic acid, fluazinam, fluidapyr, fluoxastrobin, fluquinconazole, fludioxonil, fluxapyroxad, fluquinconazole, furametpyr, fluquinconazole, furametrdazole, fluquinconazole, furametronazole, fluquinconazole, fluquinamide, fluquinconazole, propiconazole, florylpicoxamide, hexaconazole (hexaconazole), benalaxyl (benalaxyl), benalaxyl-M (benalaxyl-M), benalaxyl (benodanil), benomyl (benomyl), pefurazoate (pefurazoate), penconazole (penconazole), pencycuron (pencycuron), benzovindiflupyr (benzovindifiumper), thiocyanobenzothiazole (benthiazole), benthiavalicarb (benthiazole), penthiopyrad (penethylpyrad), flufen (penflufen), boscalid (boscalid), fosetyl (fosetyl) (aluminum (aluminium), calcium (calcium), sodium (sodium), polyoxin (polyoxin), ziram (polymannuin), carmichine (carbomermacopel), polycarb (borbamate), pyrimethanil (bromcarb), pyrimethanil (methoprene), pyrimethanil (methoprene), pyrimethanil (methocarbamil), pyrimethanil (methocarbamil (methocarbamyl-M), pyrimethanil (propiram (propicarb-M), metiram, metyltetraprole, metconazole (metconazole), metominostrobin (metinostrobin), metrafenone (metrafenone), mepanipyrim (mepanipyrim), meperfluorfen (mefenflurazone), meptyldinocap (meptyldinocap), meptyldinocap (mepronil), iodopropynyl butylcarbamate (iodocarb), laminarin (laminarins), Rhizobium vitis (Rhizobium vitas), phosphorous acid and salts (phophorous acid amides), copper oxychloride (copperoxochloride), silver (silver), cuprous oxide (cuproxoxide), copper hydroxide (copperhydroxide), potassium bicarbonate (potassium bicarbonate), sodium bicarbonate (sodium bicarbonate), sulfur sulfate (CAS), quinoline disulfide (CAS), benzoic acid diester (BAIFNYNOF-4), benzoic acid (BAIFYNOF-3-1231214), copper sulfate (BAIFYNOF-4, BCK-5, BCK-3-4, BCK-5, BCK-4-benzoic acid (BCN-5-4, BCK-3-4-5-4-BCT-4, BCT-3-4, BCT-2, BCT-4, BCT-2, S-2, BCT-2, S, 4-2, S, 3-2, 4, S, UK-2A (number), dodecyl benzene sulfonic acid bis (ethylene diamine) copper complex salt [ II ] (DBEDC), MIF-1002 (number), NF-180 (number), triphenyl tin acetate (TPTA), triphenyl tin chloride (TPTC), triphenyl tin hydroxide (TPTH), and nonpathogenic horseradish rot pathogen.

Next, well-known herbicide compounds, plant growth regulator compounds, which may be mixed or used in combination, are exemplified.

The weeding active ingredients are as follows:

ioxynil (ioxynil), aclonifen (aclonifen), acrolein (acrolein), azafenidin (azafenidin), acifluorfen (acifluorfen) (including salts with sodium and the like), azimsulfuron (azimsulfuron), asulam (asulam), acetochlor (acetochlor), atrazine (atrazine), anilofos (anilofos), amicarbazone (amicarbazone), amidosulfuron (amisulfuron), fenapyr (amitrole), pyrimethanil (amicarbazone-methyl), ametryn (amicarbazone), alachlor (amicarbazone), ametryn (amicarbazone), isofenthim (isofenuron), cyprodin (aminocyclopyrachlor), isofenuron (isofenuron), isofenuron (isofenpyrazone), isofenpyrozone (isofenuron) (including salts with sodium and the like), isofenpyroxim (isofenpyrazone), isofenpyrone (isofenpyrazone), isofenpyrozone (isofenuron) (including salts with sodium, isofenpyrozone), isofenpyrozone, isoproxide (isofenpyrozone, isoproxide, isoproxil, isoproxylon, isoproturon, isoproxil, isoproturon, Imazapyr (including salts with isopropylamine and the like), imazamethabenz (z-methyl), imazethapyr (imazamox), imazethapyr (imazapyr), imazosulfuron (imazosulfuron), indoxazol (indofluam), indoxacarb (indofenolan), glycazone-ethyl (eglinazine-ethyl), esprocarb (esprocarb), ethametsulfuron (ethofulfon), ethalfluralin (ethofulalin), sulfothioron (ethidimuron), ethoxysulfuron (ethofulfon), ethoxysulfuron (ethofenprox), ethoxysulfuron (ethoxysulfuron), bensulponin (ethoxysulfuron), benoxacor (ethoxysulfuron) (oxacor (ethoxysulfuron), benoxacor (ethoxysulfuron) (including benoxacor (ethoxysulfuron), bensulfuron), benoxacor (ethoxysulfuron) (benoxacor (ethoxyfen), bensulfuron) (benoxacor (ethoxyfen), benoxacor (ethoxysulfuron) (benoxacor (ethoxyfen) (benoxacor (methyl), benoxacor (ethoxysulfuron), benoxacor (ethoxyfen), bensulfuron) (benazol (benoxacor (benazol), benazol (benazol, Carfentrazone-ethyl, tetramine (karbutilate), diacyl-amine (carbetamide), quizalofop-ethyl, quizalofop-P-ethyl, quinclorac (quinmerac), cumyluron (cuyluron), clofentrazone (cloyfos), glyphosate (glyphosate) (including sodium, potassium, amine, propylamine, isopropylamine, dimethylamine or trimethylsulfur and the like), glufosinate (including salts with amine or sodium and the like), glufosinate (glufosinate-P), glufosinate-sodium (glufosinate-P), propyzamide (clofenamate), propyzamide (clofenamate (clofenamidopropyl-P), propyzamide (clofenamidopropyl-P), clofenamidopropyl-ethyl (clofos), propyzamide (clofen-P), clofenamidopropyl-P (clofen (clofenamidopropyl), clofen (clofen) (including salts), clofen (clofenamidopropyl-P), clofen (clofen-P), clofen-clofen (clofen-clofen), clofen (clorac) (including salts), clodinium (clomebutan) and the salt of the like), clofena, Chloramben (chlorimben), chloraminophen (chloridazon), chlorimuron-ethyl (chlorimuron-ethyl), chlorsulfuron (chlorisulfuron), dimethyl chlorophthalate (chlorithazol-dimethyl), methicillin (chlorithiamid), chlorophthalimide (chloriphthali), chlorfluazuron (chloriphthali), chlorflufluoren-methyl (chloriflurenol-methyl), chlorpropham (chlorinaphanm), chlorfluron (chlorimuron), chlorsulfuron (chlorimuron), chlortoluron (chlortoluron), ketospiroxy (ketospirox) (including salts of sodium, calcium or ammonia, etc.), saflufenacil (saflufenacil), sarmentine (sarmentine), cyanazine (cyanazine), cyanamide (cyhalodiamide), tyramine (tyrocine), diclofen (acetochlor), diclofen-diethyl-ethyl (dichloromethion), dichlormetachlor (sodium, dichlorphenazone, or the like), diclofen (dichlorphenazone, diclofen-ethyl, diclofen, etc. (including salts of sodium, diclofen, etc.), diclofen, and so on (clodinil) (including sodium, diclofen, etc.) diclofop-P-methyl, diclofop-methyl, dichlorprop-P, dithiopyr (diquat), dithiopyr (dithiopyr), siduron (siduron), dinoamine (dinitramine), cinidon-ethyl, cinosulfuron (cinosulfuron), dinotefuran (dinotefuran), diflufenzopyr (diflufenzopyr), simazine (simazine), dimethomorph (dimethomorph), dimethenamid (dimethenamid), dimethenamid (dimethenamid-P), dimethenamid (dimethenamid), dimethenamid (dimethenamid), dimethenamid (dimet, Sulfosulfuron (sulfosulfuron), sulfometuron-methyl (sulfometuron-methyl), sethoxydim (sethoxydim), terfenadine (terbacil), dicumuron (daimuron), zamethamine A (thaxtomin A), dalapon (dalapon), thiazopyr (thiozopyr), butafenacil (tiafenacil), thifensulfuron-methyl (including sodium salt, methyl ester, etc.), thiocarb (tiocarbazil), thiobencarb (thiobencarb), thidiazuron (thidiazuron), thifensulfuron-methyl (thidiazuron), thiamethoxam (desmediphenom), dimethomon (desmethyl), metosulam (thifenthifenuron), tebutrione (tebutrione), tebutrion (tebutrion), tebutrion (tebuthioxanthone), tebutrione (tebutrione), tebuthiometrizone (tebutrione), tebutrione (tebutrione), tebuthiozone (thifluzone), tebutrione (tebutrione), tebutrione (tebuthiourone), tebuthiopyrazone (tebuthionone), tebuthionone (tebuthionine), tebuthionine (tebuthionine), tebuthionone (tebuthionone), tebuthionone (tebuthionine), tebuthionine, flubenfop-methyl-M-methyl-pyrifos (triafamone), triallate (tris-aluminate), metribuzin (trietazine), triclopyr (triclopyr), butoxyethyl triclopyr (triclopyr-butyl), triflusulfuron (tritosulfuron), triflumuron (triflusfuron-methyl), trifluralin (trifluralin), trifloxysulfuron-sodium (triflusulfuron-sodium), tribenuron (tribenuron-methyl), tolpyrate (naproxen), naproxen (naproxamide) including salts with sodium and the like, naproxen (naproxen), naproxen-M (propaferon-M), nicosulfuron (nicosulfuron), nicosulfuron (nifron), dinafur (halon-methyl), pyrane (pyrazone), pyraflufen (halofop-methyl), pyrazone (halofop), pyrazone (halofop-methyl-ethyl), pyrazone (halofop), halofop (halofop), halofop (P), halofop (P), n, P (, Flupyrazoxyfen (haloxyfop-ethyl), nitrofen (halosafen), halosulfuron-methyl (halosulfuron-methyl), picloram (picloram), picolinafen (picolinafen), fluroxypyr (bicyclophoron), bispyribac-sodium (bispyribac-sodium), pinoxaden (pinoxaden), bifenox (bifenox), pyrazofos (piperophos), pyraclonil (pyrasulfolonil), pyraflufen (pyrasulfotole), pyrazoxazole (pyrazoxyfen), pyrazosulfuron ethyl (pyrazosulfuron-ethyl), pyrazosulfuron (pyrazosulfuron-ethyl), pyrazofos (biopyrifos), pyrazofos (pyrazofos-ethyl), pyrazofos (pyrazofos), pyrazosulfuron-ethyl (pyrithion-ethyl), pyrithiobac (pyrithion), pyrithiobac (pyrazone), pyrithiobac (pyrifos), pyrifos (pyrifos), pyrithion-methyl), pyrithiobac (pyrithion-methyl), pyrithion (pyrithiobac (pyrithion), pyrithion (pyrithion), isoxabenone (fenoxasulfone), fenoxaprop (fenoxaprop) (including methyl, ethyl, isopropyl), fenoxaprop-P (fenoxaprop-P) (including methyl, ethyl, isopropyl), fenkurozone (fenquintrione), thiabendazole (fenthiaprop-ethyl), fentrazamide (fentrazamide), phenmedipham (phenmedipham), foramsulfuron (foramsulfuron), butachlor (butachlor), butafenacil (butafenacil), butafenacil (buticachloride) (including methyl, ethyl, isopropyl), butafenamate (buthyl), fluazifop (methyl-ethyl), fluazifop-P (including fluazifop), fluazifop (fluazifop-P (fluazifop-P), fluazifop-P (fluazifop-P), fluazifop (fluazifop-P (fluazifop), fluazifop-P (fluazifop-P), fluazifop (fluazifop-P, fluazifop, fluazifo, Pyraflufen-ethyl (flurazolate), fluometuron (fluometuron), fluoroglycofen-ethyl (fluoroglycofen-ethyl), flucarbazone-methyl (flucarbazone-sodium), flufenacet (fluchloroalin), flucetosulfuron (flucetosulfuron), metribuzin (flufenacet-methyl) (salts including sodium, calcium or ammonia), flufenacet (flufenacet), flupyridate-ethyl (flufenpyrazosulfuron-ethyl), tetrafluoropropionic acid (flupanate), flufenpyrazam (fluoxamine), flumioxazin (flufenacet), flumethazine (flufenacet-penetryn), flufenuron (flufensulfuron-ethyl), flumetsulam (flufensulfuron-methyl), fluridone (flufenfluridone) (methyl flufenfluridone, flufenfluridone (flufenuron-methyl), fluridone (flufenfluridone) (salts including sodium, flufenfluridone, fluridone (flufenfluridone), fluridone (flufensulfuron-methyl), fluridone (flufenfluridone (flufenuron-methyl), fluridone (flufenuron, fluridone) (salts including fluridone (fluridone, flufenoxafen-methyl), fluridone (fluridone) (methyl), fluridone (fluridone ) (fluridone, fluridone) (salts including fluridone, fluridone) (salts of benfluridone, fluridone) (methyl, fluridone, Propaquizafop (propaquizafop), propyzamide (propachlor), propaquizine (propaquizine), propanil (propanil), propyzamide (propyzamide), propisochlor (propysochlorchloride), propyrisulfuron (propyrisulfuron), propaquizam (propaquizal), flumetsulam (profluor zol), prohexadione-calcium (prohexadione-calcium), prosulfenuron (propycarbazone), prosulfone sodium (propycarbazone-sodium), cycloxydim (profoxydim), canavanine (bromoacil), brompyrazone (bromopyrazone), prometryn (metryn), prometryn (metopon), bromoxynil (including esters of butyric acid, caprylic acid or heptanoic acid, etc.), bromphenoxime (bromoflufen), butachlor (bromflufenacet), butafenacet (bromfluroxypyr), butafenacet (flufenacet), butafenacetron (flufenacet), flufenacet (flufenacet), flufenacet (flufen), flufenacet (flufen), flufenacet (flufen), flufenacet (flufenacet, Pelargonic acid (pelargonic acid), phenthodim (bencorabamzone), pendimethalin (pendimethalin), bensulfuron-methyl (benzfendizone), bensulide (bensulide), bensulfuron-methyl (bensuluron-methyl), benzobicylon (benzobicyclon), pyroxene (benzofenap), bentazone (bentazone), mechlorfenpyr (pentachlor), cyclopentaxadione (penoxcarbazone), flumetsulam (bensulosin), benfuresate (benfuresate), glufosinate (fosamine), fomesafen-ethyl (fomesafen), foramsulfuron (formasulfuron), 2-methyl-4-chloropropionic acid (mesopropp) (including sodium, potassium, isoethamine, triethanolamine, dimethylamine, etc.), 2-methyl-propyl methacrylate (propanamide), thiamethoxam (thiamethoxam-methyl), pyrazosulfuron-methyl (thiamethoxam), pyrosulfuron-methyl (propanamide), pyrone (thiamethoxam, etc.), thifensulfuron-methyl (thiamethoxam), pyrone (thiamethoxam, etc. (including sodium, metosulam, metosul-methyl), pyrone, thiamethoxam, etc. (including sodium, metosul-methyl), pyrone, metosul-methyl, metosul-methyl, metosul, Metamifop (metamifop), metam (metam), disodium methyl arsenate (DSMA), methizolin (methiozolin), metsulfuron (methydymron), metoxuron (metoxuron), metosulam (metosulam), metsulfuron-methyl (metsuluron-methyl), bromogluron (metoromuron), pyroxuron (metobenuron), metolachlor (metolachlor), metribuzin (metribuzin), methoprimisulfuron chloride (mepiquat chloride), mefenacet (mefenacet), monosulfuron (monsulfuron) (including methyl, ethyl, isopropyl, monolinuron (moneron), molinate (molinate), iodosulfuron-methyl, iodosulfuron-sodium (iodosulfuron-methyl-dimethyl), sulfosulfuron (2-trifloxysulfuron), sulfosulfuron (2-trifloxysulfuron), trifloxysulfuron (2), trifloxysulfuron, a, Salts of calcium, ammonia, or the like), 2,3, 6-trichlorobenzoic acid (2,3,6-TBA), 2,4, 5-trichlorophenoxyacetic acid (2,4,5-T), 2, 4-dichlorophenoxyacetic acid (2,4-D) (including salts of amine, diethylamine, triethanolamine, isopropylamine, sodium, lithium, or the like), 2-amino-3-chloro-1, 4-naphthoquinone (ACN), 2-methyl-4-chlorophenoxyacetic acid (MCPA) (including sodium, ethyl, or the like), 2-methyl-4-chlorophenoxybutyric acid (MCPB) (including sodium, ethyl, or the like), 4- (2, 4-dichlorophenoxy) butyric acid (2,4-DB), 4, 6-dinitro-O-cresol (DNOC) (including salts of amine, sodium, or the like), and mixtures thereof, AE-F-150944 (No.), F9600 (No.), IR-6396 (No.), Desmodium officinale (MCPA-thioethyl), SYP-298 (No.), SYP-300 (No), dimethenamid (EPTC), S-metolachlor (S-metolachlor), S-9750 (No), MSMA (MSMA), HW-02 (No).

Plant growth regulator:

1-naphthylacetamide (1-naphthylacetamide), 1-methylcyclopropene (1-methylcyclopropene), 2,6-diisopropylnaphthalene (2, 6-diisoprophylnaphthalene), 4-oxo-4- (2-phenylethyl) aminobutyric acid (chemical name, CAS registry number: 1083-55-2), 4-chlorophenoxyacetic acid (4-CPA), n-decanol (n-decanol), tetrakistroestrone (aviglicidine), pyrimidinol (ancymidol), abscisic acid (abscisic acid), sodium ethoxide (inabofide), indoleacetic acid (indole acetic acid), indolebutyric acid (indole butyric acid), uniconazole (uniconazole-P), ecolysit, indazole (ester), vinyl propiolactone (choline), propiolactone (propiolactone), calcium formate (carbomethoxylactone), calcium formate (carvacoline (calcium formate), calcium formate (calcium chloride), calcium chloride (calcium chloride), calcium chloride (calcium chloride), calcium chloride (, Cloxyfonac (cloxyfonac), cloxyfonac-potassium salt (cloxyfonac-potassium), cloxyfol (cycloprop), chlormequat chloride (chlormequat), choline (choline), cytokinin (cyclokinins), cyclanilide (cyclanilide), difuranic acid (dikegulac), gibberellic acid (gibberella acid), thionine (dimethipin), azocine (sintofungen), butyrhydrazide (daminozide), thidiazuron (thidiazuron), triacontanol (triacontanol), trinexapac-ethyl, bakuchin (paclobutrazol-ethyl), paraffin (paraffin), flumetramine (flumerin), pyrimethanil (clopidogrel), carboxyfluorenol (flufenanol), jasmonate (jasmonate), spiroxamine (jasmonate), calcium chloride (chlorambucil), chlorambucil (chloramide), chlorambucil (chlorambucil), chlorambucil (halonil), chlorambucil (halonil), chlorambucil), thiflubenzuron (halonil), thiflubenzuron (chloride), calcium chloride (chloride), chlorambucil (chloride), chlorambucil (chlorambucil.

Next, well-known phytotoxicity-reducing compounds that can be mixed or used in combination are exemplified.

Isoxadifen, isoxadifen-ethyl, oxaziclofenac (oxabetrinil), cloquintocet-mexyl, phoropteryl (diethofenate), mefenapyr (dietholate), chloracet (cyclotrinil), dichlormid (dichlormid), dicyclonone (dicyclonone), copamide (cyprofamide), 1,8-Naphthalic Anhydride (1, 8-napthalenic Anhydride), fenchlorazole (fenchlorazole-O-ethyl), fenclorim (fenclorim), furilazole (furilazole), fluxofenam (fluxofenam), fluzazole (flurazole), benzoxydim (benoxazocor), mefenamate (mefenate), phnefen (fenpyr), ethyl ester of menpyrazole (npyrazole), diethyl ester of mexadifen-ethyl), mefenapyr-ethyl (mepyrazole-2-ethyl-2- (PPG-2-ethyl-2-propenyl) -2- (2-ethyl-methyl-ethyl-2, PPG-2-ethyl-2- (2-methyl-ethyl-2, 2-methyl-ethyl-2-methyl-ethyl-2, PPG-2-ethyl-2, 2-ethyl-2, 2-ethyl-2-methyl-ethyl-2-ethyl-2, and methyl-ethyl-2-ethyl-, 2-dichloromethyl-2-methyl-1, 3-dioxane (MG-191), 3-dichloroacetyl-2, 2, 5-trimethyl-1, 3-oxazolidine (R-29148), 4-dichloroacetyl-1-oxa-4-azaspiro [4,5] decane (AD-67), MON4660 (No.), metacamifen, N1, N2-diallyl-N2-dichloroacetyl glycine amide (DKA-24), TI-35 (No.).

The pest control agent of the present invention having the above-described structure exhibits an excellent controlling effect on pests such as orthoptera pests, thysanoptera pests, hemiptera pests, coleopteran pests, diptera pests, lepidoptera pests, hymenoptera pests, rhabdoptera pests, thysanoptera pests, cockroaches pests, isoptera pests, gnathida pests, trichophagous pests, phthiridae pests, plant parasitic mites, plant parasitic nematodes, plant parasitic mollusks, other harmful animals, harmful pests, sanitary pests, and parasites. As these harmful organisms, the following species can be exemplified.

Examples of the orthopteran pest include: grass family black shank forehead grass (russula lineosa), etc.; yellow-face oil gourd (Teleogryllus emma), cricket (Truljalia hibonis) and the like of the family Gryllus chinensis; mole cricket (Gryllotalpa orientalis) of the family mole cricket; oryza minuta (Oxya hyla intercatee), Oryza migratoria (Locusa migratoria), Henocardia sanguinea (Melanoplus sanguinipes), Crispa unilocusta (Melanoplus difficile), and Blueda fusca (Melanoplus femurrubem) of the family Acridae; long locusta migratoria (Atractomorpha lata) of the acrididae family; cricket japonicas (Euscyrtus japonicum) of acridicaceae; locusta (Xyajaponicum) belonging to the family locustidae, etc.

Examples of pests of the order thysanoptera include: frankliniella quinquefolia (Frankliniella intnsa), Frankliniella occidentalis (Frankliniella occidentalis), Scirtothrips tabashioris (Scirothrix dorsalis), Thrips palmi (Thrips palmi), Thrips tabaci (Thrips tabaci), Thrips tabani (Thrips setosus), Thrips greenhouse (Heliothrips halothrips hamoides), Thrips oryzae (Stenchaethrips biformis), etc., Frankliniella kaki (Pontiothyrips dioxapyropsis), Thrips mustarum mustard (Liothrips wasbiae), Thrips oryzae (Haplothrips aculatus), etc., of the family Cirsidaceae.

Examples of hemipteran pests include: cicada (Mogannia minuta) of the cicada family; lawfish (Aphrophora intermedia) of the family Lasiocladiaceae, etc.; cicadas (Machaerotypus sibiricus) of the family cicadae, and the like; grape leafhoppers (arboricula apiculata), tea leafhoppers (Empoasca onaukii), black tail leafhoppers (Nephotettix cincticeps, Nephotettix malayanus), two-point black tail leafhoppers (Nephotettix virases), two-spot black tail leafhoppers (Nephotettix nigroticus), electrooptic leaf hoppers (recilias dorsalis), two-point green leaf hoppers (Amrasca biguttlula), fruit brown leaf hoppers (Idioscopus nitidus, Idioscopus typhyllus, Amritodatkinsonii), potato leafhoppers (Empoasca fabae), and the like; cercospora castanea (pentastidium apacalis) of the family cercosphacidae, and the like; laodelphax striatellus (Laodelphax striatellus), Nilaparvata lugens (Nilaparvata lugens), Sogatella furcifera (Sogatella furcifera) and the like of the family Laodelphadae; trident deltoid (Nisia nervosa) of veitchy medicinaceae; kamendaka saccharoivora of Chanxiong family, etc.; achilus flumeus of the family Delphacidae, etc.; orosana japonica of Paracicadae, Orosana japonica, etc.; cicada (Mimophantia maritima) of the family cicadae, etc.; psyllium (Cacopsylla pyricularia), Trialeyrodids (Diaphorina citri), etc. of the family psyllidae; mango whitewood louse (Calophya mangiferae) of the family limnoporaceae, and the like; a grape root aphid (Daktulosphaira vitiliae) of the family of the Rhizosteraceae, etc.; (ii) Myzus larvatus (Adelges larcis), Myzus ferrugineus (Adelges tsugae), etc., of the Myzudaceae family; piperium pisum (Acyrthosporium pisum), Aphis gossypii (Aphisgossypii), Aphis spiraefolia (Aphis spiraecola), Aphis Raphanus (Lipaphis erysimi), Aphis brassicae (Brevicornus hybrid), Aphis persicae (Myzuspiericae), Aphis graminis (Schizaphis graminum), Aphis graminicola (Rhopalosiphum padi), Aphis citricola (Toxoptera aurantii), Aphis solanacearundii (Auricularia solomorpha), Aphis maxima (Macrosiphum eupatorium), Aphis lactuca (Nasonophila ribissnigi), Aphis graminis (Sitobion avena aveae), Aphis soyae (Aphis glabra), and the like; camellia plenoporus calalliae (Aleurocoanthus calalliae), Aleurocoanthus spiniferus (Aleurocoanthus spiniferus), Bemisia tabaci (Bemisia tabaci), Bemisia argenteus (Bemisia argentifolia), Trialeurodescales (Trialeurodesvaporariorum), etc.; drosicha corpulenta, Icerya purchasi, etc., of the family lecanicolaceae; pink scales (Dysmicoccus brevicum), citrus pink scales (Planococcus citri), and Congylodes (Pseudococcaceae comstocki) of the family Lecanidae; ericerus pela (Ceroplasmes ceriferus), Ericerus pela (Ceroplasmes rubens), etc., of the family Geckiaceae; sugarcane rancko (Aclerda takahashii) of the family Ericeryaceae, etc.; red round scale (Aonidiella aurantii), pear round scale (Diaspidiotus pernicious), white mulberry scale (Pseudoaulacaspipartagoa), arrowhead scale (Unnaspascensis), etc., of the pelothyridae family; lygus pratensis (Lygus lineolaris), Lygus lucorum (Trigonotylus caelilium), Lygus lucorum (Apolygus lucorum), heaven Ailanthus (Nesidiococcus tenuis), Toona sinensis (Halticus brachycanthus), etc., of the family lyridae; reticulum coronarium (stephanis pyrioides), lygus pyricularis (stephanis nashi), etc., of the family reticulidae; stinkbug (eurydemarrugosum), stinkbug (eyarselilisi), stinkbug (eyarsaris aeneus), rice brown stinkbug (Lagynotomus elongatus), rice green stinkbug (Nezara viridula), stinkbugs (platia crocosa), Oryza sativa stinkbug (Nezara antennata), brown stinkbugs (eushistulose heros), etc., of the family Ailantidae; stinkbug (megacoptachribraria) of the family of turgididae, and the like; chinese toon (Urochela luteoviria) of the family Isocaudaceae, and the like; sugar cane bugs (caverius saccharoivorus) of the family lyridae, and the like; lygus japonicus (Malcus japonica) of lygus lucorum, and the like; red plant bug (dysdermus cingulatus) of family red plant family, etc.; stinkbug (leptocisa acuta), chinosid (leptocisa chinensis), etc., of the family arachnidaceae; stringylon dolorum (anacantharis striicornis) of the family lyridae, and the like; lygus luteus (Rhopalus macculatus) of the family melioideae, and the like; and Cimex lectularis (Cimex lectularis) of family cimicidae.

Examples of coleopteran pests include: tortoise (Tortoise, etc.), Tortoise (Anomaria cuprea), Tortoise (Poillia), Anomala geniula, Rhinoceros, Tortoise (Heptophila picea), etc.; agriotes ogarae, Elaphanoplosis latus (Agrioteslineatus), Elaphanotus obliquus (Agriotes obstrus), Melanotus okinawensis, Melanotus fortnumi, etc., of the family click beetle; small bark beetles (Anthrenus versasci) of the family bark beetles, and the like; heterodentate ips (Heterobotrytis hamatopennis) of the family Pectinopidae, and the like; medicinal material A (Stegobium paniceum) of family Tolypocladiaceae, etc.; brown spider nails (Pitinus clavipes) of arachnidae, and the like; giralla tamansi (Tenebriodes manritanicus) of Gularnaceae, and the like; red foot Guoshi (Neolobia rufipes) of the family Guoshi; yellow spot outmodex (carbophilus hemipterus), rape floral outmodex (meligethe aeneuus), etc.; rice flat worms of the family amelogidae (Ahasverusadvena), and the like; gibberella dersonii (Cryptolepes ferrugineus) of the family Hypocrealiaceae; e.varivestis (Epilachna varivestis) of the family of ladybirdae, E.varivestis (Henosapillara virginioticus) of the family of ladybridae, etc.; tenebrio molitor (Tenebrio molitor), Tribolium castaneum (Tribolium castaneum), etc., of the family Arthropodidae; bean-genkwa (epiceuta gorhami) of the family of the genkwa, etc.; anoplophora glabripennis (Anoplophora glabripennis), Tiger cantoniensis (Xyloterchus pyrroderus), Monochamus alternatus (Monochamus alternatus), and Chordopodium ambrosioides (Deces texanus) of the family Anoplophorae; phaseolus vulgaris (Callosobruchus chinensis) of Viridae, etc.; the species Buchloa tuberosa (Leptinotarsa decemlineata), corn rootworm (Diabrotica virgifera), northern corn rootworm (Diabrotica barberi), Diabrotica unicinica (Diabrotica unicincatata Howardii), yellow dawnia (Autoclava febraylis), Calophylla minor (Phaedon brassica), Begonia sinensis (Cassia alburena), Torulopsis oryzae (Oule oryzae oryza), Laurena mexicana (Epilachnaissaries), Phyllotreta flava (Phytolta), Phytodora trifoliata (Demous scabaria), Phyllospora lanuginosa (Psyllidactyla chloa), Phytoloma lata (Ceratoptera trichocarpa), Phyllospora, Phyllostachydia japonica (Coloniana, etc.; sweet potato weevil (Cylas forminarius) of the family of Trichineniaceae, etc.; weevil (Hypera stictica), vegetable weevil (Listroderis costrostris), western Indian sweet potato weevil (Euscapes postfascia), Quercus mongolicus (Curculio sikkimensis), etc.; elephants of the family of the weevilidae (Echinochnemus bipunctus), elephants of rice (Lissophorus oryzae), Oryzophagosoryzae, etc.; elephant of ambroxobidae (Sitophilus zeamais), turf ambroxburgh weevil (Sphenophrus chinensis), etc.; bark beetles (Tomicus piniperda) of the family bark beetles; tairius coccineus (Crossotarsus niponicus) of family Pectenopideae, etc.; and the Liriopus punctatus (Lyctus brunneus) of the family of the meal beetles.

Examples of dipteran pests include: giant rice mosquitoes (Tipula aino) of the family macromosidae, and the like; black midge (Plecia nearctica) of the family anopheles; exechia shiitakevora of the family Mycolecidae, and the like; potyxiascobiii (Pnyxiascaabiei), Bradysia agrestis, etc., of the Arctiidae family; soybean pod gall midge (Aspongylia yushimaia), wheat gall midge (Mayeiola destructor), Dasineura oxycacana, etc., of the gall midge family; aedes aegypti (Aedes aegypti) of the family Culicidae, Culex pipiens pallens (Culex pipiens), and the like; arachnocampa nikoensis (Simuliumtakahashii) of the family Arachnocampaceae, etc.; chironomus oryzae (Chironomus oryzae) of Chironomus; tabanus densatus (Chrysopsssuavis), Tabanus deltoides (Tabanus tridenus), etc., of Tabanidae; amycophophaga cepacia (Eumerussrigatus) of the family Aphididae, etc.; citrus fruit fly (Bactrocera dorsalis), Japanese cherry fruit fly (Euphratajaponica), Meristotheca mediterranean (Ceratitis capitata), etc. of the family Bactroceraceae; liriomyza sativae (Liriomyza trifolii), Liriomyza sativae (Liriomyza sativae), oryza japonica (Agromyza oryzae), Liriomyza lyconiae (Liriomyza sativae), Liriomyza sativae (chromomatosa horticola), Liriomyza sativae (Liriomyza sativae), Liriomyza trifoliae (Liriomyza trifolii), and the like; black-belly wheat-straw flies (Meromyzanigeniristis) of the family Drosophilaceae, etc.; cherry fruit fly (Drosophila suzukii), Drosophila melanogaster (Drosophila melanogaster), etc. of the Drosophilaceae family; leaf miner (hydralli griseola) of the family hydroviridae, and the like; horse lice fly (hippoposica equina) of the family pedicellaceae, etc.; sasa veitchii of the family Bosiromyidae (Parallepmma sakawae), etc.; seed flies of Allium fistulosum (Delia antiaqua) and Gray seed flies (Delia platura) of the family Drosophilaceae; lavatories (Fanniacanicularis) of the family lavatoriidae, and the like; houseflies (Musca domestica), stable flies (Stomoxys calcerns), etc., of the family Musca; sarcophaga peregrina (Sarcophaga peregrina) of the family Sarcophagidae, and the like; gasterophilus intestinalis (Gasterophilus intestinalis) of the family Gasterophilaceae, etc.; dermatidae (Hypoderma lineatum), etc.; and ovine flies (Oestrusovis) of the family Muscadae.

Examples of lepidopteran pests include: hepialus pallidus (endosilica excrescens) of hepialidae, and the like; grape moth (Antispila ampelopsia) of the family Helicoveridae, and the like; six-star black-spot moth (Zeuzereuconotum), aromatic wood moth (Cossus insularis), etc., of the family Carpinidae; cabbage loopers (Archipusfoscarpus) of the family Tolypocladidae, tea leaf loopers (Adoxophyes orana fasciata), Grapholita molesta, tea leaf loopers (Homona magnanima), soybean pod borers (Leguminivoranlla), codling moth (Cydia pomonella), grape flower wing loopers (Lobesia botana), and the like; glossy privet leaf roller moth (Eupoecilia ambiguella) of the family Tolypocladidae, and the like; bambarina sp of Hypocrealidae, Eumycotina virginiana (Eumycotinusula), etc.; a rice moth (Nemapogon granella) of the family Bombycidae, a Chlamydomonas (Tenea translucens), etc.; a fruit moth (Buccularx pyrivorella) of the family Micromoth, etc.; peach leaf miners (Lyonetia clerkella), Lyonetia prunifoliella malinella, etc., of the family Potentillaceae; tea-fine moth (Caloptilia theivora) of the family Hyphantriaceae, Spodoptera littoralis (Phyllonorycter rinoniella), and the like; citrus leaf miners (phyllocnisticitrella) of the family citrinopteraceae, and the like; cabbage moth (Acrolepiopsis sapporensis) of the family Acropteraceae, etc.; diamondback moth (Plutella xylostella) of the family Plutella, apple moth (Yponomeuta orientalis) of the family Bombycidae, and the like; argyresthia conjugella (Argyresthia conjugella) of the family Bombycidae; grape fruit tree (Nokona regalis), apple fruit tree (paranthadin fruit) and the like; tuber moths of the family Conidioidae (Phthirius operculella), wheat moths (Sitotroga cerealella), pink bollworms (Pectinophora gossypiella), tomato leaf miners (Tutaabsoluta), and the like; moth (Carposina sasakii) of the family mothidae, and the like; pieris punctata (Illiberi pruni) of the family Mylopodae, etc.; yellow moth (Monema flavescens) of the family spiny moth, etc.; the families of the grasses include the rice nestling borer (Antylomia japonica), Chilo suppersalis (Chilo suppersalis), Cnaphalocrocis medinalis (Cnaphalocrocismedinalis), Asian corn borer (Ostrinia furnacalis), cabbage borer (Hellula undalis), peach borer (Conogethes punctiferalis), Diaphania pyralis (Diaphania indica), early maturing grass borer (Parapedialis tetrerella), European corn borer (Ostrinia nubilalis), and the like; sugarcane borer (Diatraea saccharalis), stem borer (Cadra cautella) of the family Bombycidae, wax borer (Galleria mellonella), and the like; grape moths (Nippoptilia vitas) of the family Bombycidae, and the like; papilio xuthus (Papilio xuthus) of Papilionaceae, etc.; pieris rapae (Pieris rapae) of family Pierisceae, etc.; tapioca rectilineata (Paranara guttata) of the family Tapioideae, and the like; giant bridgeworm (Ascotis selenaria) of the family Spodopterae, and the like; red pine caterpillar (Dendrolimus spectabilis), yellow brown tenella (Malacomonas neustrium testaceum), etc. of the family Corynonaceae; white potato hornworm (Agrius convoluli) of family hawkmothae, and the like; tea caterpillars (Ara pseudoconspersa), Orygia recans approximanis, Lymantria dispar, etc. of the family Pothidae; hyphantria cunea (hypanthria cunea) of the family lampridae, and the like; cutworm (Agrotis ipsilon), cutworm (Agrotis segetum), soybean silverworm (autographa), cotton bollworm (Helicoverpa armigera), Spodoptera frugiperda (Helicoverpa zea), Spodoptera exigua (Helicoverpa zea), tobacco budworm (helicopters virescens), Spodoptera exigua (Spodoptera exigua), prodenia litura (Spodoptera), soybean Spodoptera exigua (chrysodex includens), Spodoptera frugiperda (Spodoptera frugiperda), Spodoptera coptera cunea (neuropoles minians), and the like.

Examples of hymenoptera pests include: ogillidae (Arge pagana) of Argillidae, etc.; peak of chestnut (Apethylmus kuri) of Meliaceae, Pterocarpus albus (Athalia rosae ruficornis) and the like, gall of chestnut (Dryocosmus kurihilus) of gall wasp and the like; yellow sparrow bees (Vespa micromimaxanthoptera) of the family vespidae, and the like; solenopsis invicta (Solenopsis invicta), Argentina ant (Linepihema hugie), etc. of the family Formicidae; and a leaf cutting wasp (Megachile nipponica) belonging to the family Apidae.

Examples of the pests of the order of the Collembola include: and Bouletiella palmeriana (Bouletiella palmeri) belonging to the family Boulexidae.

Examples of pests of the order thysanoptera include: and chlamydomonas (Lepisma sacchara) and chlamydomonas (Ctenolepisma villosa) belonging to the family Chlamydomonaceae.

Examples of pests of the order blattaria include: periplaneta americana (Periplaneta americana) of Blattaceae, Blattella germanica (Blattella germanica) of Blatta family, and the like.

Examples of the isoptera pests include: termites albizzia chinensis (inc.) termites of the family termitiaceae, etc.; termites of the family Noptotermes formosanus (Coptotermes formosanus), etc.; odontotermes formosanus (odontottermes formosanus) of the family termitaceae, and the like.

Examples of pests of the order rodentia include: ground tea borers (Trogium pulsatorium) of the family of the rodenticaceae, and the like; liposcelis corrodens of the family Pediculidae, and the like.

Examples of the eardrum pests include: red earwigs (labodora riparia) of the earwig family, and the like.

Examples of the trichophagous pests include: chicken lice of the family brachiocladium brachypodae, etc., and boapparent lice of the family odontobiridea (Damalinia bovis), etc.

Examples of the louse pests include: pig blood lice (Haematopinus suis) of the blood lice family, and the like; pediculus humanus (Pediculus humanus) of the family Pediculus humanus, etc.; acanthamopsis (linoganthus setosus) of the family japonicaceae, and the like; and pubic lice (Pthirus pubis) of the family pubic lice.

Examples of the pests of the order acarina include: tetranychus urticae (Penthaleus major) of the family Pedaliaceae, and the like; tarsonemus pallidus (Phytonemus pallidus), Tarsonemus laterosus (Polyphaga terreus), etc., of Tarsonemus tarsonchidae; spike mites (Siteropes sp.) of the family Tyrophagaceae, and the like; grape short-hair mite (brevippus lewisi) of the family of finefiber mites; demodex malacopsis (Tuckerella pavonioformis) of Demodex family, etc.; tetranychus beii (Eotetranychus boreus) of the Tetranychidae family, Tetranychus citriodorus (Panychus citri), Tetranychus ulmi (Panychus ulmi), Tetranychus urticae (Tetranychus urticae), Tetranychus mirabilis (Tetranychus kanzawai), and the like; terra trichophytes (Trisetocus pini) of the family Nagochaetaceae, and the like; aculops pelekassi of the gall mite family, Onychia pyrifera (Epitrimerus pyri), Citrus rust mite (Phyllocoperuta oleivora), Lycopersicon esculentum (Aculopsophilerici), etc.; diptacus crenatae of the family of the Onychidae; aleurophagus ovatus (aleurophagus ovatus), Tyrophagus putrescentiae (Tyrophagus putrescentiae), and root mites (rhizophyllus robini) of the family aleyrodidae; acarina dersoniana (Ornithonyssus sylvialum) of the family Girales; varroa jacobsoni (Varroa jacobsoni) of varroaceae, and the like; dermanyssus gallinae (Dermanyssus gallinae) of Dermanychidae, etc.; acarina dersoniana (Ornithonyssus sylvialum) of the family Girales; boophilus microplus (Boophilus microplus), Rhipicephalus sanguineus (Rhipicephalus sanguineus), Haemaphysalis longicornis, etc. of the family Acarinaceae; sarcoptes scabies (Sarcoptes scabies) of the family sarcoptedae, and the like.

Examples of plant parasitic nematodes include: standard sisal (xiphilinema index) of the longneedle family, etc.; burseraceae, Paradera minutissima (Paratrichororus minor), etc.; one of the family of the Bacteroides (genus Rhabditella sp.) and the like; one of the family Leptodermaceae (Meloidogyne incognita, Aglenchus sp.) and the like; one of the Astradaceae (Nematospora cephalatus sp.) and the like; strawberry bud nematode (Notopterylenchus acris), potato stem nematode (Ditylenchus destructor) of the family granulophilaceae, and the like; reniform nematodes (rotylenchulus reniformis), helicobactor palaestis (Helicotylenchus dihystera), etc. of the family of the zonaceae; needle-family curved needle nematodes (Paratylenchus flavtatus), and the like; meloidogyne incognita (Meloidogyne incognita), Meloidogyne hapla (Meloidogyne hapla), etc., of the family Meloidogyne; helicoverpa tuberosa (Globodera rostochiensis), Meloidogyne solanacearum (Globodera pallida), Heterodera glycines (Heteroderaceae), etc.; purslane dwarf nematode (Tylenchynchus clavulioni) of the family Lepidaceae, and the like; one of the nude nematodes of the family gymnocomiaceae (genus fasciculus, Psilenchus sp.) and the like; a kind of a nematode (rotifer sp.) belonging to the family Cyclotellidae, etc.; hemipuncture nematodes (Tylenchulus semipenetrrans) of the hemipuncture family; caenorhabditis elegans (Sphaeronema camelliae) of the family caenorhabditis elegans, and the like; sphaeronema camelliae, Radophocephalus citrullus, Radopholus banana, Nacobber aberrans, Pratylenchus penetrans, and Pratylenchus coffea of the family Brachypodaceae; stropharia umbellata (Iotonchium angustifolium) of the family Conidiodaceae, and the like; aphelenchoides (Aphelenchus avenae) of aphelenchoideae, and the like; aphelenchoides besseyi (Aphelenchoides besseyi), Aphelenchoides strawberry (Aphelenchoides fragariae), and the like, belonging to the family aphelenchaceae; bursaphelenchus xylophilus (Bursaphelenchus xylophilus) of the family Rhynchophyllus, and the like.

Examples of the plant-parasitic mollusk include: pomacea canaliculata (Pomacea canaliculata) of the family Spirochaetaceae, etc.; slugs (Leaviculis alte) of the family Bursapridae, etc.; african large snail (Achatina furica) of African large snail family, etc.; slugs (slugs) of the family myxophilic slugidae, etc.; succinealauta of Conus Snailaceae, etc.; shallow disc snail (disc roupper) of disc snail family; amber snail family shrimp and lily shell (Zontoides yessoensis); slugs of the family slugidae (Limax flavus), slugs of the valencia (Lehmannia valmentana), slugs of the wild (deraceras reticulatum), etc.; parakalliella halinensis of the family Anacardiaceae, and the like; lucuma ball snail (Acusta despecta sieboldiana), Bradybaena hominis (Bradybaena similis) and the like belonging to the family Bauscidae.

Examples of pests such as other harmful animals, undesirable animals, sanitary pests, livestock pests, and parasites include: procambarus clarkii (Procambarus clarkii) of Procambarus clarkii family of the order of Tenpoda; armadillidium vulgare (Armadillidium vulgare) of the family Strongylocentronidae of the order Isopodales; armadillidium vulgare (Armadillidium vulgare) of the family Toxoviride, and the like; scutigera spp of Scutigera order, Vietnamese Scopologes of Scopologes order, and the like; pest of the order Diplopoda such as greenhouse Marble (Oxidus gracilis) of the family Thamnoideae of the order Marylales; theridaidaehasselii of the family Valerianaceae, and the like; red chelidosa (Chiracanthium japonicum) belonging to the order Araneidae; scorpions (Androctonus crassicaulus) of order turkey; ascarids (ascaridides) as parasites in linear animals; pinworms (sypharmacia sp), and the like; wuchereria banzensis (Wuchereria benchmark), and the like; hemicdellidis gigantea (Distomum sp.), Poecilobdella pulchella (Paragonimus westernmanii), Achnum transversum (Metagonimus yokokawai), Schistosoma japonicum (Schistosoma japonicum), Taenia solium (Taenia solium), Taenia bovis (Taeniahynchus sangnatus), Echinococcus sp., and Taenia megalophaticus (Diphyllothrix latum), which are endoparasites of platyhelminth, and the like.

The pest control agent of the present invention exhibits a control effect on the pests and the like described above, which have acquired resistance to conventional pest control agents. The pest control agent of the present invention can also be used for plants having characteristics such as pest resistance, disease resistance, herbicide resistance, and the like obtained by gene recombination, artificial mating, or the like.

Next, the preparation method, formulation method and use of the compound of the present invention are illustrated in detail by the following examples, but the present invention is not limited to these examples at all. The melting point, which is a physical property of the compound of the present invention, was measured by using an MP-500V melting point Trace measuring apparatus manufactured by ヤナコ. The refractive index was measured by using an abbe refractometer manufactured by アタゴ.¹H nuclear magnetic resonance spectroscopy was performed by using J manufactured by Japan ElectronNM-LA400(400MHz), JNM-LA300(300MHz) or JNM-ECS300(300MHz), with Tetramethylsilane (TMS) as an internal standard. High Resolution Mass Spectrometry (HRMS) was measured using QOxactive Focus Hybrid Quadrupole-Orbitrap LC-MS/MS System (ESI, positive mode) manufactured by サーモフィッシャーサイエンティフィック.

Also disclosed is a method for producing an intermediate for producing the compound of the present invention.

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