TW201841890A - Novel 1-phenylpiperidine derivative and agricultural/horticultural drug agent including same as effective component - Google Patents

Abstract

The purpose of the present invention is to provide a novel 1- phenylpiperidine derivative and an agricultural/horticultural drug agent including the compound as an effective component, in particular a novel 1-phenylpiperidine derivative useful for an agricultural/horticultural pest control agent, tick/mite control agent, nematode control agent and the like, and a production method and method of use thereof. Provided are a 1-phenylpiperidine derivative represented by a formula, N-oxide thereof, or a salt thereof. [In the formula: R is, for example, a C1 -6 alkyl group or a C1 -6 haloalkyl group; X is, for example, a C1 -6 alkyl group, a C1 -6 haloalkyl group, a halogen atom, or a cyano group; Y is, for example, a halogen atom; Z is, for example, a C1 -6 haloalkyl group; n is an integer of 0, 1, or 2; and m is an integer of 1 to 3.].

Description

Novel 1-phenylpiperidine derivatives and agricultural and horticultural agents using the same as active ingredients

The present invention relates to a novel 1-phenylpiperidine derivative, an agricultural and horticultural agent using the compound as an active ingredient, especially an agricultural and horticultural pest control agent, a mite control agent or a nematode control agent, and a method for using the same .

In the field of agriculture and horticulture, plant pest control agents for the purpose of controlling various pests and diseases have been developed and put into practical use. However, the emergence of pesticide-resistant pests or diseases has become a problem, and the development of novel pharmaceutical agents is eagerly awaited. Patent Document 1 describes that a 1-phenylpiperidine derivative is useful as an insecticide for animals. However, Patent Document 1 does not disclose a compound obtained by directly introducing the sulfur-containing substituent of the present invention as a substituent at the 3-position of the phenyl group of a 1-phenylpiperidine derivative. Furthermore, an additional test was performed on the compound described in Patent Document 1, and as a result, it was found that the effects on the mites were insufficient. In addition, as similar compounds of the compounds of the present invention, the following compounds have been disclosed (for example, Patent Documents 2 to 3). However, the chemical structures of these compounds disclosed in Patent Documents 2 to 3 are different from the compounds of the present invention. [Prior Art Literature] [Patent Literature] [Patent Literature 1] International Publication No. 2006/087162 [Patent Literature 2] Japanese Patent Laid-Open Publication No. 2015-036377 [Patent Literature 3] International Publication No. 2015/091267

[Problems to be Solved by the Invention] In the production of agricultural and horticultural crops, the damage caused by pests and diseases is still large at present, and the development of new agricultural and horticultural applications is expected due to the emergence of resistant diseases and pests against existing medicines. Pharmacy. [Technical means to solve the problem] The present inventors have repeatedly studied in order to solve the above problems, and found that a 1-phenylpiperidine derivative represented by the formula (I) below as a novel compound not described in the literature is used as a farm The medicament for art, especially the pest control agent for agriculture and horticulture, the mite control agent or the nematode control agent is more useful, thus completing the present invention. That is, the present invention relates to a 1-phenylpiperidine derivative represented by the following formula (1), an N-oxide or a salt thereof, an agricultural and horticultural agent using the compound as an active ingredient, and a method of using the same , And its manufacturing method, [Wherein R represents a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, and a C _2-6 haloalkynyl group , C _3-6 cycloalkyl C _1-6 alkyl or C _3-6 halocycloalkyl C _1-6 alkyl, X represents C _1-6 alkyl, C _1-6 haloalkyl, C _{3- 6} cycloalkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _2-6 haloalkenyl, C _2-6 haloalkynyl, C _1-6 alkoxy, C _1-6 haloalkoxy , C _3-6 halocycloalkyl, C _1-6 alkoxymethyl, C _1-6 haloalkoxymethyl, optionally substituted benzyloxymethyl, C _1-6 alkoxycarbonyl , C _1-6 alkylcarbonyl, hydroxymethyl, formamyl, halogen atom, cyano, amine, nitro, -CH = NOR ¹ , 2,2-dicyanovinyl, represented by the following formula A, or a saturated heterocyclic ring containing oxygen or sulfur, Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group, Z may be the same or different, and represents a C _1-6 haloalkyl group, and R ¹ represents a C _1-6 alkyl group, C _1-6 haloalkyl, or benzyl, n represents an integer of 0, 1 or 2, and m represents an integer of 1 to 3]. [Effects of the Invention] The compounds of the present invention exhibit excellent effects as agricultural and horticultural agents, especially agricultural and horticultural pest control agents, mite control agents, nematode control agents or disease control agents. It is also effective against pests that are parasitic on animals such as dogs and cats, or domestic animals such as cows and sheep.

In the definition of the substituent represented by the above formula (I), a halogen atom means a chlorine atom, a bromine atom, an iodine atom or a fluorine atom, and the so-called C_1-6 Alkyl (for groups containing this group as a substituent, e.g. C_3-6 Cycloalkyl C_1-6 C in the case of alkyl, etc._1-6 Alkyl group is the same, and the following is also the same for other groups), for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, n-pentyl Alkyl groups having 1 to 6 carbon atoms, such as isopentyl, neopentyl, tertiary pentyl, n-hexyl, isohexyl, and the like; C_1-6 Haloalkyl means a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different. Examples include fluoromethyl, chloromethyl, Difluoromethyl, trifluoromethyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl Methyl, 2-iodoethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2,2-difluoroethyl, 1-fluoroisopropyl , 3-fluoropropyl, 3-chloropropyl, 3-bromopropyl, heptafluoropropyl, heptafluoroisopropyl, 4-fluorobutyl, 4-chlorobutyl, nonafluorobutyl, etc. A linear or branched haloalkyl group having 1 to 6 carbon atoms substituted by 9 halogen atoms. As C_2-6 Examples of alkenyl include vinyl, allyl, isopropenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-pentenyl, and 3-pentene Methyl, 4-pentenyl, 1,1-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 1-methyl-2-butenyl, 1-methyl-3-but Alkenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3 -Butenyl is equal to a linear or branched alkenyl group having 2 to 6 carbon atoms having at least one double bond at any position. As C_2-6 Examples of the haloalkenyl group include 1-fluorovinyl group, 2-fluorovinyl group, 2,2-difluorovinyl group, 3-chloro-2-propenyl group, and 3,3-difluoro-2-allyl group. , 3,3-dichloro-2-allyl, 4,4,4-trifluoro-2-butenyl, 4,4,4-trifluoro-3-butenyl, 5-chloro-3- The pentenyl group and 6-fluoro-2-hexenyl group are equal to a straight or branched chain alkenyl group having 2 to 6 carbon atoms substituted with 1 to 9 halogen atoms having at least one double bond at any position. As C_2-6 Examples of the alkynyl group include ethynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 1-butynyl, and 2-butynyl. Alkynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3 -Butynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1-methyl-3-pentynyl, 1-methyl-4 -The pentynyl group is equal to a linear or branched alkynyl group having 2 to 6 carbon atoms having at least one triple bond at any position. As C_2-6 Examples of haloalkynyl include fluoroethynyl, 4,4,4-trifluoro-2-butynyl, 5,5,5-trifluoro-3-pentynyl, 1-methyl-3,3, 3-trifluoro-2-butynyl, 1-methyl-5,5,5-trifluoro-2-pentynyl is equal to a carbon substituted with 1 to 9 halogen atoms having at least one triple bond at any position A linear or branched alkynyl group having a number of 2 to 6. As C_3-6 Cycloalkyl means, for example, a cycloalkyl group having 3 to 6 carbon atoms having a cyclic carbon number such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. As C_1-6 Examples of the alkoxy group include methoxy, ethoxy, n-propoxy, isopropoxy, cyclopropoxy, n-butoxy, second butoxy, third butoxy, and n-pentyl A linear or branched alkoxy group having 1 to 6 carbon atoms such as an oxy group and a n-hexyloxy group. As C_1-6 Examples of the haloalkoxy group include fluoromethoxy, dichloromethoxy, trichloromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, and bromodifluoromethoxy. Methyl, dichlorofluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2,2- Trifluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 1-fluoroisopropoxy, 3-fluoropropoxy, 3-chloropropoxy, 3-bromoprop The alkoxy group, 4-fluorobutoxy group, 4-chlorobutoxy group and the like are preferably a linear or branched alkoxy group having 1 to 6 carbon atoms substituted with 1 to 9 halogen atoms. As C_1-6 Examples of the halocycloalkyl group include 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, and 1-chloro Cyclopropyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 2,2-dibromocyclopropyl, 1-fluorocyclobutane Base, 2-fluorocyclobutyl, 3-fluorocyclobutyl, 3,3-difluorocyclobutyl, 3,3-dichlorocyclobutyl, 1-fluorocyclopentyl, 2-fluorocyclopentyl, 3-fluorocyclopentyl, 2,2-difluorocyclopentyl, 3,3-difluorocyclopentyl, 2,2-dichlorocyclopentyl, 1-fluorocyclohexyl, etc. are preferably 1-9 A halogen cycloalkyl group having 1 to 6 carbon atoms substituted by a halogen atom. As C_3-6 Cycloalkyl C_1-6 Examples of the alkyl group include cyclopropylmethyl, 2-cyclopropylethyl, 3-cyclopropylpropyl, 4-cyclopropylbutyl, 5-cyclopropylpentyl, and 6-cyclopropyl. Hexyl, cyclobutylmethyl, cyclopentylmethyl and other groups. As C₃ ~ C₆ Halocycloalkyl C₁ ~ C₆ Examples of the alkyl group include 1-fluorocyclopropylmethyl, 2-fluorocyclopropylmethyl, 2,2-difluorocyclopropylmethyl, 2-chlorocyclopropylmethyl, and 2,2- Dichlorocyclopropylmethyl, 2- (2,2-difluorocyclopropyl) ethyl, 2- (2,2-dichlorocyclopropyl) ethyl, 3- (2,2-difluorocyclo Propyl) propyl, 4- (2,2-difluorocyclopropyl) butyl, 5- (2,2-dichlorocyclopropyl) pentyl, 6- (2,2-difluorocyclopropyl ) Hexyl, 2,2-difluorocyclobutylmethyl, 2,2-dichlorocyclobutylmethyl, 3,3-difluorocyclopentylmethyl, 3,3-dichlorocyclopentylmethyl, 4,4 -Groups such as difluorocyclohexylmethyl or 4,4-dichlorocyclohexylmethyl. As C_1-6 Examples of the alkoxycarbonyl group include methoxycarbonyl, ethoxycarbonyl, n-propylcarbonyl, n-butylcarbonyl, n-pentylcarbonyl, n-hexylcarbonyl, and isopropylcarbonyl groups. Examples of the saturated heterocyclic ring containing oxygen include 1,3-dioxolane and 1,3-dioxane. Examples of the saturated heterocyclic ring containing sulfur include 1,3-dithiane and 1,3-dithiocyclopentane. Examples of the substituent in the benzyloxymethyl group which may be substituted include a halogen atom, a methyl group, an ethyl group, and a methoxy group. Examples of the salt of the 1-phenylpiperidine derivative represented by the formula (I) of the present invention include hydrochloride, or inorganic salts such as sulfates, nitrates, and phosphates; and acetates; or Organic acid salts such as fumarate, maleate, oxalate, mesylate, benzenesulfonate, and p-toluenesulfonate. The 1-phenylpiperidine derivative represented by the above formula (I) of the present invention may include one or more asymmetric centers in its structural formula, and there may be two or more optical isomers and non- In the case of mirror image isomers, the present invention also includes all optical isomers and mixtures containing them in an arbitrary ratio. In addition, the 1-phenylpiperidine derivative represented by the formula (I) of the present invention may have two geometric isomers derived from a carbon-carbon double bond in its structural formula. The present invention also includes all Each geometric isomer and a mixture containing them in an arbitrary ratio. Among the compounds of the present invention, R is preferably C_1-6 Alkyl, C_1-6 Haloalkyl or C_3-8 A cycloalkyl compound, more preferably R is C_1-6 Alkyl, C_1-6 Haloalkyl compounds. Among the compounds of the present invention, preferably X represents C_1-6 Alkyl, C_1-6 Alkoxymethyl, cyano or halo compounds, more preferably X is C_1-3 Alkyl, C_1-3 Alkoxymethyl, chlorine, bromine or cyano compounds. In the compound of the present invention, Y preferably represents a hydrogen atom, a halogen group, or C_1-6 The alkyl compound is more preferably a compound in which Y represents a halogen group. Among the compounds of the present invention, preferably Z represents C_1-6 The haloalkyl compound is more preferably a compound in which Z represents a fluoroalkyl group. Among the compounds of the present invention, a compound in which m represents an integer of 1 to 3, and a compound in which m represents 1 is more preferable. A representative method for producing the novel 1-phenylpiperidine derivative represented by the above formula (1) and the 1-phenylpiperidine derivative represented by the following formula (3) as an intermediate is disclosed below However, the present invention is not limited to these methods. Reaction 1[Wherein X represents C_1-6 Alkyl, C_1-6 Haloalkyl, C_3-6 Cycloalkyl, C_2-6 Alkenyl, C_2-6 Alkynyl, C_2-6 Haloenyl, C_2-6 Haloalkynyl, C_1-6 Alkoxy, C_1-6 Haloalkoxy, C_3-6 Halocycloalkyl, C_1-6 Alkoxymethyl, C_1-6 Haloalkoxymethyl, optionally substituted benzyloxymethyl, C_1-6 Alkoxycarbonyl, C_1-6 Alkylcarbonyl, hydroxymethyl, formamyl, halogen atom, cyano, amine, nitro, -CH = NOR¹ , 2,2-dicyanovinyl, A represented by the following formula, or a saturated heterocyclic ring containing oxygen or sulfur,Y represents hydrogen atom, halogen atom, C_1-6 Alkyl or C_1-6 Haloalkyl, Z may be the same or different, indicating C_1-6 Haloalkyl, R¹ Means C_1-6 Alkyl, C_1-6 Haloalkyl, or benzyl, halo¹ And halo² Each independently represents a halogen atom, and m represents an integer of 1 to 3] In the method shown in Reaction Formula 1, the 1-phenylpiperidine derivative represented by the above formula (3) can be produced by: The phenyl compound represented by the formula (5) and the piperidine compound of the formula (6) are reacted in an inert solvent in the presence or absence of a base. The solvent used in the reaction between the compound of the formula (5) and the compound of the formula (6) can be widely used without particular limitation as long as it is a solvent inactive for the reaction. Examples of such a solvent include alcohols such as methanol, ethanol, n-propanol, and isopropanol; aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane; or benzene, chlorobenzene, Aromatic hydrocarbon solvents such as toluene and xylene, halogenated hydrocarbon solvents such as dichloromethane, 1,2-dichloroethane, and chloroform; ether solvents such as diethyl ether, tetrahydrofuran, and 1,4-dioxane; methyl acetate Ester solvents such as esters, ethyl acetate, ketone solvents such as acetone, methyl ethyl ketone, amine solvents such as N, N-dimethylformamide, nitrile solvents such as acetonitrile, and propionitrile, N-formaldehyde Aprotic polar solvents such as pyrrolidone and N, N'-dimethylimidazolinone. These solvents can be used individually by 1 type or in mixture of 2 or more types as needed. As the base used in the reaction between the compound of the formula (5) and the compound of the formula (6), known inorganic bases and organic bases can be used. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate, and sodium bicarbonate; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and alkali metal hydrides such as sodium hydride and potassium hydride. Examples of the organic base include alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide, and amines such as triethylamine and pyridine. These alkalis can be used individually by 1 type or in mixture of 2 or more types. Such a base can be used in an amount of usually 1 to 100 equivalents, preferably 1 to 2 equivalents, based on the phenyl compound represented by the formula (5). Regarding the use ratio of the phenyl compound represented by the formula (5) to the piperidine compound represented by the formula (6), it is more preferable to use the piperidine compound at 1 to 2 moles relative to the phenyl compound (5). (6). This reaction can usually be carried out at a temperature ranging from -78 ° C to the boiling point of the solvent used, and preferably at room temperature to 100 ° C. The reaction time varies depending on the reaction temperature and the like, and cannot be generalized. The reaction usually ends in about 0.5 to 24 hours. The target compound obtained by each of the above reactions can be easily isolated from the reaction mixture by a conventional isolation method, such as an organic solvent extraction method, or a chromatography method, a recrystallization method, a distillation method, or the like. Refining is performed by a usual refining method. Reaction 2[Where X, Y, Z, R, halo¹ And m is as defined above] In the method shown in the reaction formula 2, the 1-phenylpiperidine derivative represented by the above formula (2) is produced by making the above formula (3) The 1-phenylpiperidine compound is reacted with the thiol compound of the above formula (4) in an inactive solvent in the presence or absence of a base. As the solvent used in the reaction between the 1-phenylpiperidine derivative of the above formula (3) and the thiol compound of the above formula (4), as long as it is a solvent which is inactive to the reaction, a known one can be widely used. Solvent. Examples of such solvents include alcohols such as methanol, ethanol, n-propanol, and isopropanol; aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane; benzene, chlorobenzene, and toluene Aromatic hydrocarbon solvents such as xylene, halogenated hydrocarbon solvents such as dichloromethane, 1,2-dichloroethane, chloroform, ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, and methyl acetate , Ester solvents such as ethyl acetate, amine solvents such as N, N-dimethylformamide, solvents such as N-methylpyrrolidone, N, N'-dimethylimidazolinone, and acetonitrile. These solvents can be used individually by 1 type or in mixture of 2 or more types as needed. As the base used in the reaction of the compound of the formula (3) and the compound of the formula (4), known inorganic bases and organic bases can be used. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate, and sodium bicarbonate; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and alkali metal hydrides such as sodium hydride and potassium hydride. Examples of the organic base include alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide, and amines such as triethylamine and pyridine. These alkalis can be used individually by 1 type or in mixture of 2 or more types. Such a base can be used in an amount of usually 1 to 100 equivalents, preferably 1 to 2 equivalents, based on the 1-phenylpiperidine derivative represented by the formula (3). The use ratio of the 1-phenylpiperidine derivative of the above formula (3) to the thiol compound represented by the above formula (4) can be appropriately selected from a wide range, and it is better than the former one mole It is preferable to use the latter after 1 to 5 moles, and more preferably to use the latter after 1.0 to 2.0 moles. This reaction is preferably performed at a temperature ranging from room temperature to the boiling point of the solvent used, and more preferably at a temperature ranging from room temperature to heating under reflux. Regarding the reaction time, the reaction usually ends in about 0.5 to 24 hours. After completion of the reaction, it is only necessary to isolate the reaction system containing the target substance by a conventional method, and if necessary, the target substance can be manufactured by recrystallization, column chromatography, or the like. In addition, the target substance may not be isolated from the reaction system and may be used in the next reaction step. Reaction Formula 3[Where X, Y, R, Z, halo¹ And m is as defined above, and M represents chlorine, bromine, iodine, tosylate, mesylate or trifluoromethanesulfonate] In the method shown in Reaction Formula 3, the above formula (2) The 1-phenylpiperidine derivative is produced by reacting the 1-phenylpiperidine derivative represented by the above formula (3) with an alkali metal sulfide such as sodium sulfide. After the thiol derivative represented by the formula (7), the thiol derivative and the alkylating agent of the formula (8) are reacted in an inert solvent in the presence or absence of a base. As the solvent used in the reaction between the 1-phenylpiperidine derivative of the formula (3) and the alkali metal sulfide, a known solvent can be widely used as long as the solvent is inactive for the reaction. Examples of such solvents include alcohols such as methanol, ethanol, n-propanol, and isopropanol, and ammonium-based solvents such as N, N-dimethylformamide and N, N-dimethylacetamide. , Ether solvents such as tetrahydrofuran, 1,4-dioxane, ester solvents such as methyl acetate, ethyl acetate, N-methylpyrrolidone, N, N'-dimethylimidazolinone, dimethyl Solvents such as fluorene and acetonitrile. These solvents can be used individually by 1 type or in mixture of 2 or more types as needed. Examples of the alkali metal sulfide used in the reaction include sodium sulfide, sodium sulfide hydrate, sodium hydrogen sulfide, potassium sulfide, and lithium sulfide. Such an alkali metal sulfide can be used in an amount of usually 1 to 20 equivalents, preferably 1 to 2 equivalents based on the 1-phenylpiperidine derivative represented by the formula (3). The use ratio of the 1-phenylpiperidine derivative of the formula (3) to the alkali metal sulfide can be appropriately selected from a wide range, and it is preferably 1 to 5 moles compared to the former one mole. The latter is more preferably the latter using 1.0 to 2.0 mol. This reaction is preferably performed at a temperature ranging from room temperature to the boiling point of the solvent used, and more preferably at a temperature ranging from room temperature to heating under reflux. Regarding the reaction time, the reaction usually ends in about 0.5 to 24 hours. After the reaction is completed, it is only necessary to separate the reaction system containing the target by a conventional method. If necessary, the target can be manufactured by recrystallization, column chromatography, or the like, and the target can be produced without the reaction system. The target is isolated and used in the next reaction step. As the solvent used in the reaction between the thiol derivative represented by the above formula (7) and the alkylating agent of the above formula (8), a known solvent can be widely used as long as the solvent is inactive to the reaction. . Examples of such solvents include alcohols such as methanol, ethanol, n-propanol, and isopropanol; ammonium solvents such as N, N-dimethylformamide, tetrahydrofuran, and 1,4-dioxane. Ether-based solvents, ester-based solvents such as methyl acetate and ethyl acetate, solvents such as N-methylpyrrolidone, N, N'-dimethylimidazolinone, dimethylsulfinium, and acetonitrile. These solvents can be used individually by 1 type or in mixture of 2 or more types as needed. As the base used in the reaction between the thiol derivative of the formula (7) and the alkylating agent of the formula (8), known inorganic bases and organic bases can be used. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate, and sodium bicarbonate, and alkali metal hydroxides such as sodium hydroxide and potassium hydroxide. Examples of the organic base include amines such as triethylamine and pyridine. These alkalis can be used individually by 1 type or in mixture of 2 or more types. Such a base can be used in an amount of usually 1 to 20 equivalents, preferably 1 to 4 equivalents, relative to the thiol derivative of the formula (7). The use ratio of the thiol derivative of the above formula (7) and the alkylating agent of the above formula (8) can be appropriately selected from a wide range, and preferably 1 to 5 is used relative to the former of 1 mole. It is more preferable to use the latter from 1.0 to 2.0 moles. This reaction is preferably performed at a temperature ranging from room temperature to the boiling point of the solvent used, and more preferably at a temperature ranging from room temperature to heating under reflux. Regarding the reaction time, the reaction usually ends in about 0.5 to 24 hours. After completion of the reaction, it is only necessary to isolate the reaction system containing the target substance by a conventional method, and if necessary, the target substance can be manufactured by recrystallization, column chromatography, or the like. In addition, the target substance may not be isolated from the reaction system and may be used in the next reaction step. Reaction 4[Wherein X, Y, R, Z and m are as defined above] In the method shown in Reaction Formula 3, the 1-phenylpiperidine derivative represented by the above formula (7) can be obtained by the above formula (2) Manufactured by the oxidation reaction of the 1-phenylpiperidine derivative shown. As the solvent used in the oxidation reaction of the 1-phenylpiperidine compound represented by the formula (2), a solvent which is inactive to the reaction can be widely used. Examples of such a solvent include aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene, dichloromethane, Halogenated hydrocarbon solvents such as 1,2-dichloroethane and chloroform; alcohol solvents such as methanol and ethanol; ester solvents such as methyl acetate and ethyl acetate; ketone solvents such as acetone and methyl ethyl ketone; N, Ammonium solvents such as N-dimethylformamide, nitrile solvents such as acetonitrile, propionitrile, aprotic polar solvents such as N-methylpyrrolidone, N, N'-dimethylimidazolinone, etc., Acetic acid. These solvents can be used individually by 1 type or in mixture of 2 or more types as needed. Examples of the oxidizing agent used in the oxidation reaction of the 1-phenylpiperidine compound represented by the formula (2) include m-chloroperbenzoic acid, sodium periodate, hydrogen peroxide, and tributyl hypochlorite. , Sodium hypochlorite and so on. Such an oxidizing agent can be used in an amount of usually 1 to 3 equivalents, preferably 1 to 2.5 equivalents based on the 1-phenylpiperidine derivative represented by the above formula (2). Sodium tungstate dihydrate can be added as a catalyst. The sodium tungstate dihydrate can be used in an amount of usually 0.001 to 0.2 equivalents, preferably 0.001 to 0.1 equivalents, based on the 1-phenylpiperidine derivative. This reaction can usually be carried out at a temperature ranging from -78 ° C to the boiling point of the solvent used, and preferably from 0 ° C to room temperature. The reaction time varies depending on the reaction temperature and the like, and cannot be generalized. The reaction usually ends in about 0.5 to 24 hours. The target compound obtained by each of the above reactions can be easily isolated from the reaction mixture by a conventional isolation method, such as organic solvent extraction, chromatography, recrystallization, distillation, etc. Refining is usually performed by a refining method. A representative compound of the 1-phenylpiperidine derivative represented by the formula (1) of the present invention is shown in Table 1 below, and the 1-phenylpiperidine derivative represented by the formula (3) of the present invention is shown below. Representative compounds are shown in Table 2 below, but the scope of the present invention is not limited to these compounds. Furthermore, the compounds included in the present invention may have optical isomers resulting from the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms. The present invention includes all optically active substances, racemic Stereoisomers or non-mirromeric isomers. In addition, the physical properties in the table indicate properties and melting points (° C), "n-" indicates positive, "s-" indicates second, "t-" indicates third, "cy-" indicates a ring, and "i-" indicates "Me" means methyl, "Et" means ethyl, "Pr" means propyl, "Bu" means butyl, and "Ph" means phenyl. Formula (1)Table 1 Table 2 The compounds of the present invention can be used in agriculture, indoors, and forests for hygiene of livestock and in various scenarios to prevent or repel harmful organisms. Specific usage scenarios, target pests, and usage methods are disclosed below, but the content of the present invention is not limited to these. The compound of the present invention represented by the above formula (1) can also be used for controlling crops, for example, food crops (rice, barley, wheat, rye, oats and other wheat, corn, potato, sweet potato, taro, soybean, red bean, Broad beans, peas, beans, groundnuts and other beans), vegetables (cabbage, cabbage, radish, turnip, broccoli, cauliflower, komatsu, cruciferous crops, pumpkin, cucumber, watermelon, cantaloupe, melon and other melon, eggplant, tomato , Green pepper, pepper, okra, spinach, lettuce, coriander, carrot, burdock, garlic, onion, shallot, etc.), mushrooms (shiitake, mushroom, etc.), fruit trees, fruits (apple, citrus, pear, Grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, strawberries, etc., spices and other ornamental objects (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), special-purpose crops (tobacco, Tea, sugar beet, sugar cane, hops, cotton, hemp, olives, rubber, coffee, etc., forage, fodder (timothy grass, alfalfa, alfalfa, corn, sorghum, orchard grass, rice grass, legume grass) Wait ), Zoysia (Korean grass, Begonia, etc.), forest trees (Sakhalin fir, fish scale spruce, pine, cypress, fir, cypress, etc.), or ornamental plants (chrysanthemum, rose, Herbs such as carnations, orchids, flowers, ginkgo, cherry blossoms, garden trees such as Tochigi coral, etc.) damage arthropods, molluscs, nematodes, and fungi, myxomycetes, bacteria, actinomyces Pests such as fungi and bacteria. Examples of specific pests include: Lepidoptera of the order Arthropoda, For example, Helicoverpa armigera of the family Noctuidae, Heliothis spp. ), Agrotis segetum, Autographa nigrisigna, Trichoplusia ni, Mamestra brassicae, Spodoptera exigua, Spodoptera exigua Spodoptera litura, etc., Plutella xylostella, etc., Adoxophyes orana fasciata, Adoxophyes honmai, Archipex fuscocupreanus , Homona magnanima, Caloptilia theivora, Grapholita molesta, etc., Eumeta minuscula, etc. Moth (Lyonetia prunifoliella malinella), Peach leaf miner (Lyonetia clerkella), etc., Phyllocnistis citrella, etc., Phyllonorycter ringoniella, etc. Acrolepiopsis sapporensis, etc., Apple wing moth (Synnanthedin hector), etc., Stathmopoda masinissa, etc., Pectinophora gossypie lla), etc., Carposina niponensis, etc., Cossus jezoensis, etc., Nemapogon granella, etc. (Monema flavecens), Parasa lepida, Scopelodes contracus, etc., Chilo suppressalis, Scirpophaga incertulas, Cnaphalocrocis medinalis ), Hellulla undalis, Conogethes punctiferlis, Diaphania indica, Parapediasia teterrella, etc., Locastra muscosalis, etc. , Parnara guttata, etc., Papilio xuthus, Papilio xuthus, etc., Pieris rapae crucivora, etc. boeticus), Ascotis selenaria, etc., Agrius convolvuli, etc., Phalera flavescens, etc. Sky caterpillar (Malacosoma neustrium testaceum), etc. Saturnia japonica, etc., Euproctis pseudoconspersa, Orygia recens approximans, etc., Spilosoma imparilis, American white Adults, larvae and eggs of moth (Hyphantria cunea), grape fruit tapeworm (Endopiza viteana), apple small roll moth (Laspeyresia pomonella), etc .; Coleoptera, such as Anomala cuprea, Japanese beetle (Popillia japonica), small blue and white beetle (Oxycetonia jucunda), yellow-green beetle (Anomala geniculata), etc., citrus narrow jiding (Agrilus auriventris), etc., Melanonotus fortnumi ), Etc., Epilachna vigintioctopunctata, etc., Anoplophora malasiaca, Xylotrechus pyrrhoderus, etc., Aulacophora femoralis, Corn root Diabrotica spp. ), Phyllotreta striolata, Cassida nebulosa, Phaedon brassicae, Oulema oryzae, Epilachna varivestis, Potato leaf beetle (Epilachna varivestis) Leptinotarsa decemlineata, etc., Rhynchites heros, etc., Cylas formicarius, etc., Curculio sikkimensis, Rice water Adults, larvae, and eggs of the weevil (Lissorhoptrus oryzophilus), Mexican cotton boll (Anthonomus gradis grandis), Sphenophrus venatus vestitus, etc., Epureae domina, etc. Heteroptera of the order Hemiptera, such as Eurydema rugosum, Eysarcoris lewisi, Eysarcoris parvus, Nezara viridula, Sri Lanka Plautia stali, Halymorpha mista, etc., Urochela luteovoria, etc., Togo hemipterus, etc. Bean bee Riptortus clavatus, Cletus punctiger, etc., Leptocorisa chinensis, etc. from the family Pygmyidae, Dysdeercus cingulatus, etc. Stephanitis nashi, Stephanitis pyrioides, etc., Apolygus spinolai, Stenotus rubrovittalus, Trigonotylus coelestialium, etc. , Adults, larvae and eggs of Megacopta punctatissimum, etc .; Homoptera of Hemiptera, such as Platypleura kaempferi, etc. Cicada (Arboridia apicalis), Small green leafhopper (Empoasca onukii), Pseudo-black-tailed leafhopper (Nephotettix cincticeps), Two-pointed black-tailed leafhopper (Nephotettix virescens), etc., Laodelphax striatellus, Brown Nilaparvata lugens, Sogatella furcifera, etc., Geisha distinctissima, etc., Psylla pyrisuga, Diaphorina citri Etc, powder Aleurocanthus spiniferus, Bemisia argentifolii, Bemisia tabaci, Dialeurodes citri, Trialeurodes vaporariorum, etc. Viteus vitifolii, etc., Aphis citricola, Aphis craccivora, Aphis gossypii, Aulacorthum solani, cabbage aphid (Brevicoryne brassicae), Toxoptera aurantii, Toxoptera citricidus, Aulacorthum magnoliae, Schizaphis piricola, Nippolachnus piri, Lipaphis erysimi, Hyalopterus pruni, Pleotrichophorus chrysanthemi, Macrosiphoniella sanborni, Megoura crassicauda, Sitobion ibarae ), Macrosiphum euphorbiae, Potato aphid (Myzus varians), Myzus persicae, Rhodolosiphum rufiabdominalis, Gramineous tuber Aphid (Rhopalosiphum padi), Longhorn wheat aphid (Sitobion akebiae), Apple aphid (Eriosoma lanigerum), etc., Icerya purchasi, etc., Pseudococcus comstocki Citronoccus viburnae, Phenacoccus kraunhiae, etc., Ceroplastes ceriferus, Ceroplastes rubens, etc., Aonidiella aurantii ), Comstockaspis perniciosa, Pseudaulacaspis pentagoa, Unaspis yanonensis, and other adults, larvae, and eggs; Thysanoptera, such as the ochre thrips ( Scirtothrips dorsalis), Thrips palmi, Thrips tabaci, Thrips setosus, Frankliniella intonsa, Frankliniella occidentalis, Greenhouse thrips haemorrhoidalis, etc., adults, larvae and eggs of Thrips Ponticulothrips diospyrosi, Haplothrips aculeatus, etc .; Hymenoptera, for example Athalia rosae ruficornis, Arge pagana, etc., Apple trigemidae (Arge mali), etc., Dryocsmus kuriphilus, etc. Megachile nipponica nipponica, etc., Formica japonica, Camponotus kiusiuensis, Lasius fuliginosus, fire ant Solenopsis richteri), invading red fire ants (S.  invicta), tropical fire ants (S.  geminata)) and other adult insects, larvae and eggs; Diptera, such as Asphondylia yushimai, etc., Rhacochlaena japonica, Bactrocera cucurbitae), Hydrellia griseola, etc., Drosophila suzukii, etc., Liriomyza trifolii, Liriomyza trifolii (Liriomyza sativae), Chromatomyia horticola, Agromyza oryzae, Liriomyza bryoniae, etc., Delia platura, Delia platura, Delia antiqua) and other adults, larvae and eggs; Orthoptera, such as Locusta migratoria, Orthoptera, Ruspolia lineosa, and yellow face oil Adults, larvae, and eggs of gourd (Teleogryllus emma), truljalia hibinonis, etc., Gryllotalpa orientalis, etc., and Orthoptera Oxya yezoensis, etc .; Isoptera ), Such as Taiwan white Adults, larvae, and eggs of Odontotermes formosanus; Dermaptera, adults, larvae, and eggs of Labidura riparia, etc. Collembola), for example, Sminthurus viridis, etc., adults, larvae, and eggs of Onychiurus matsumotoi, etc. (Isopada), such as adult, larvae, and eggs of Armadillidium vulgare; Acari, arachnid, such as Polyphagotarsonemus latus , Phytonemus pallidus, etc., Tetranychus mite (Penthaleus major), etc., Brevipalpus lewisi, Brevipalpus phoenicis Citrus panonychus citri, Panonychus ulmi, Tetranychus urticae, Tetranychus kanzawai, Amphitetranychus viennensis, Tetranychus urticae, Tetranychus urticae, Tetranychus kanzawai, Amphitetranychus viennensis Hawthorn conifer (Oligonychus ununguis), Bryobia eharai, Eotetranychus kankitus, Bryobia praetiosa, etc., Aculus Schlechtendali, Pycnididae Mite (Aculops pelekassi), Citrus mites (Phyllocoptruta citri), Chiba mites (Eriophyes chibaensis), Tulip mites (Aceria tulipae), Grape mites (Colomerus vitis), Achilles fockeui (Aculus fockeui), tea Adult mites, larvae, and eggs of the mite (Calacarus carinatus), etc., Tyrophagus putrescentiae, Rhizoglyphus robini, etc .; Archaenioglossa, the main mollusk ampullopoda , Such as Pomacea canaliculata, etc., Plumonata, such as Achatina fulica of the African snail family, Meghimatium bilineatum, and Black tadpoles (Milax gagates), tea-backed tadpoles (Lehmannina valentiana), flat snails (Acusta despecta sieboldiana), etc .; linear animals Tylenchida of the tracheid nematodes, such as Ditylenchus destructor, etc., Tylenchorhynchus claytoni, etc. Pratylenchus penetrans, Pratylenchus coffeae, etc., Helicotylenchus dihystera, etc., Globodera rostochiensis, etc. Meloidogyne incognita, etc., Criconema jaejuense, etc. of the family Ringworm, Nothotylenchus acris, etc., Aphelecchoides fragarriae, etc. Order, for example Xiphinema sp. ), Trichodorus sp. ), Etc .; fungi and bacteria such as Eumycota, Myxomycota, Bacteriomycota and Actinomycota. Specific examples of diseases to which the compound of the present invention represented by the formula (1) can be applied include rice blast (Pyricularia oryzae), flax leaf blight (Cochliobolus miyabeanus)), Rhizoctonia solani (Rhizoctonia solani), Endogenous browning disease (Pantoea ananatis), Brown stripe disease (Acidovorax avene subsp.  avenae)), leaf sheath browning (Pseudomonas fuscovaginae), leaf blight (Xanthomonas oryzae pv.  oryzae)), Bacterial blight disease (Burkholderia plantarii), etc .; wheat powdery mildew (Erysiphe graminis), scab (wheat scab) (Gibberella zeae)), red rust (Puccinia striiformis), fungal rust (P. graminis), P. stalk  recondita), P. barley  hordei)), snow rot (Typhula sp. ), Micronectriella nivalis), Smut (Ustilago tritici), U. barley (U.S.  nuda), smut (Tilletia caries), eye streak (Pseudocercosporella herpotrichoides), moire (Rhynchosporium secalis), leaves Fusarium oxysporum (Septoria tritici), Blight (Leptosphaeria nodorum), Reticulum (Pyrenophora teres), Leopard ( Helminthosporium zonatum Ikata), smut (Pseudomonas syringae pv.  japonica)), etc .; black spots of citrus (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, Italian green Mold  italicum), brown rot disease (Phytophthora citrophthora), tobacco blight  nicotianae)), black spot disease (Phyllosticta citricarpa), etc .; apple candidiasis (Apple flower rot fungus (Monilinia mali)), rot disease (Apple rot fungus (Valsa mali)), powdery mildew ( Podosphaera leucotricha), spotted leaf disease (Alternaria mali), black spot disease (Venturia inaequalis), black spot disease (Mycospherella pomi)), anthracnose (Colletotrichum acutatum), rotella (Botryosphaeria berengeriana), red spot disease (Gymnosporangium yamadae), gray star disease (Peach gray star) Monilinia fructicola), etc .; Solanacea nigra (Venturia nashicola), P. nigra  pirina), black spot disease (Alternaria kikuchiana), red spot disease (Gymnosporangium haraeanum), gray star disease (Monilinia fructigena), etc .; peach Gray star disease (Monilinia fructicola), black star disease (Cladosporium carpophilum), Phytophthora sp. (Phomopsis sp. )), Perforated bacterial disease (Brenneria nigrifluens), etc .; grape black pox (Elsinoe ampelina), rot rot (Colletotrichum acutatum), Powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii), dew disease (Plasmopara viticola )), Gray star disease (Monilinia fructigena), black star disease (Cladosporium viticolum), gray mold disease (Botrytis cinerea), root cancer bacterial disease ( Agrobacterium vitis), etc .; anthracnose of persimmon (Gloeosporium kaki), deciduous disease (Cercospora kaki, Mycoshaerella nawae), etc .; melons Anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea, Oidiopsis taurica), blight (Didymella bryoniae), stem rot (Fusarium oxysporum), dew Mycosis (Pseudoperonospora cubensis), blight (Phytophthora sp. )), Bacterial blight (Pythium sp. )), Etc .; Spotted bacterial disease of cucumber (Pseudomonas syringae pv.  lochrymans)), marginal blight disease (Pseudomonas viridiflava), brown spot disease (Xanthomonas campestris pv.  cucurbitae)) and so on; melon brown spot disease (Xanthomonas campestris pv.  cucurbitae)), hairy root disease (Agrobacterium rhizogens), cancerous disease (Streptomyces sp. )) Etc .; fruit stain of watermelon (Acidovorax avenae pv.  citrulli)), etc .; bacterial wilt of solanaceous vegetables (Ralstonia solanacearum); etc .; tomato ringworm (Alternaria solani), leaf mold (Xanthomonas campestris (Cladosporium fulvum)), blight (Phytophthora infestans), ulcer disease (Clavibacter michiganense subsp.  michiganense)), stem gangrene (Pseudomonas corrugata), soft rot (Pectobacterium carotovorum subsp.  carotovorum)), etc .; brown spot disease of eggplant (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum), etc .; black spot of cruciferous vegetables (Alternaria cabbage) japonica)), white spot disease (Cercosporella brassicae), soft rot (vegetable soft rot bacteria (Pectobacterium carotovorum subsp.  carotovorum)) etc .; the putrefaction of cabbage (Pseudomonas syringae pv.  marginalis)), black rot (Cruciferous vegetable black rot fungus (Xanthomonas campestris pv.  campestris)), etc .; rot disease of lettuce (Pseudomonas cichorii, Pseudomonas viridiflava), speckle bacterial disease (lettuce bacterial leaf spot disease Xanthomonas campestris pv .  vitians)), onion rust (Puccinia allii), etc .; soybean purple scar (Cercospora kikuchii), black pox (Elsinoe glycines), black spots Disease (Diaporthe phaseolorum var.  sojae)), etc .; anthracnose of bean (Colletotrichum lindemthianum), etc .; black rot of groundnut (Cercospora personata), brown spot (Cercospora arachidicola) Etc .; powdery mildew of peas (Erysiphe pisi); etc .; potato summer blight (Alternaria solani), blight (Phytophthora infestans) Rhizoctonia solani), etc .; strawberry powdery mildew (Sphaerotheca humuli), etc .; tea net cake disease (Exobasidium reticulatum), white star disease (Elsinoe leucospila )), Red fever disease (Pseudomonas syringae pv.  theae)), ulcer disease (Xanthomonas campestris pv.  theicola)), etc .; tobacco red spot disease (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), dew disease ( Tobacco downy mildew (Peronospora tabacina)), blight (Phytophthora nicotianae), blight (Ralstonia solanacearum), cavity disease (Pectobacterium carotovorum subsp.  carotovorum)), etc .; brown spot of sugar beet (Cercospora beticola), blight of beetroot (Aphanomyces cochliodes), etc .; black spot of rose (Diplocarpon rosae )), Powdery mildew (Sphaerotheca pannosa), etc .; brown spot of chrysanthemum (Septoria chrysanthemi-indici), white rust (Puccinia horiana), Root cancer (Agrobacterium tumefaciens), etc .; gray mold (Botrytis cinerea), sclerotinia (Sclerotinia sclerotiorum) of various crops such as eggplant, cucumber and lettuce; Snow Rot (Pythium iwayamai), Wheat Snow Rot (Tyohula incarnate), Fusarium nivale, Sclerotinia borealis (Sclerotinia borealis), Powdery mildew (Sclerotinia borealis) Gramineae (Erysiphe graminis), fairy ring disease (Lycoperdon perlatum), Lepista subnudo, Marasmius oreades), leaf-like rot (Marasmius oreades) Ceratobasidium spp. )), Rhizoctonia solani (Gaemannomyces graminis), Curvularia leaf blight (Curvularia geniculata), Leaf rot (Rhizoctonia solani) Pythium fusarium wilt (Pythium periplocum, Pythium vanterpoolii), rust (Puccinia spp. )), Coin spot disease (Sclerotinia homoeocarpa), etc .; red burn disease (Pythium aphanidermatum), anthracnose (Colletotrichum sp. )). The compound of the present invention represented by the above formula (1) can also be used to prevent damage to wood and wooden furniture, stored food, clothing, books, etc., in indoor activities in buildings including ordinary homes, or Arthropods or fungi that cause corruption and cause damage to our lives. Specific examples of the pest include the following organisms. Arthropoda termites, such as Coptotermes formosanus, Rhinoterme formosanus, Reticulitermes speratus, other termites (Reticulitermes hesperus), black embryo Scattered termites  tibialis), North American termite (R.  flavipes), Southern European Reticulated Termites (R.  lucifugus), Sante termites (R.  santonensis), Incisitermes minor, Odontotermes formosanus, Hodotermopsis jzponica of the termite family, Cryptotermes domesticus of the termite family Adults, larvae, and eggs; Coleoptera, for example, Sitophilus zeamais, Sitophilus zeamais, etc .; Callosobruchus chinensis, Bruchus pisorum , Broad bean elephant (Bruchus rufimanus), etc., Tribolium castaneum, Tribolium confusum, etc., Oryzaephilus surinamensis, Horned chest Cryptolestes pusillus, etc., Lasioderma serricorne, Stegobium paniceum, etc., Attagenus unicolor japonicus, Anthrenus verbasci), Dermestes maculatus, etc., Gibbium aequinnoctiale, etc., Dinoderus minutus, 榖 蠹 ( Rhizopertha dominica, etc., adults, larvae and eggs of Lyctus brunneus, etc .; Lepidoptera, such as Cadra cautella, Ephestia kuehniella, India Adults, larvae and eggs of Plodia interpunctella, etc., Sitotroga cerealella, etc., Tinea translucens, Tineola bisselliella, etc .; For example, Lepinotus reticulatus, etc., and adults, larvae, and eggs of the book family, Liposcelis bostrychophilus, etc .: Spodoptera, for example, Blattella germanica ), Etc., adults, larvae, and eggs of the black-brown magpie (Periplaneta fuliginosa) of the family Polygonidae, Japanese giant salamander (Periplaneta japonica), etc .; the order of the bee, such as the Monomium pharaoni of the ant family, Japanese ants (Monomorium nipponense) and other adults, larvae and eggs; Chlamydomes, such as Ctenolepisma villosa, Lepisma saccharina and other adults, larvae and eggs; Diptera, If Drosophila melangogaster, etc., and adult, larvae, and eggs of Piophila casei, etc. in the fly family; Arthropoda arachnids, such as saprophyte of the acaroid family Tyrophagus putrescentiae, Lardoglyphus konoi, etc., adults, larvae, and eggs of Carpoglyphus lactis, etc .; fungi, such as wood decay fungi, Tyromyces palustris ), Coriolus versicolor, etc .; Aspergillus niger, Aspergillus terreus, Aureobasidium pullulans, Chaetomium globosum , Cladosporium cladosporioides, Eurotium tonophilus, Fusarium moniliforme, Gliocladium virens, Myrothecium verrucaria, Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, and the like. The compound of the present invention represented by the above formula (1) can also be used to control pests that damage or weaken trees in natural forests, plantations, and urban green spaces. Specific pests include: Lepidoptera of the order Arthropoda, for example, Calliteara argentata, Euproctis pseudoconspersa, Orygia recens approximans, Orygia recens approximans, Euproctis subflava, Lymantria dispar, etc., Malacosoma neustria testacea, Dendrolimus spectabilis, Dendrolimus superans, etc., Crytoblabes loxiella, etc., Agrotis segetum, etc., Ptycholoma lecheana circumclusana, Cydia kurokoi, Cydia cryptomeriae, etc. , Spilosoma imparilis, Hyphantria cunea, etc., Stigmella castanopsiella, etc. of Micromoth, Parasa lepida, Scopelodes contracus), yellow rust spot moth (Microleon longipalpis) and other adults, larvae and eggs; Coleoptera, such as the scarab Asteraceae (Anomala) rufocuprea), small chestnut gill beetle (Heptophylla picea), etc., Agrilus spinipennis, etc., Monochamus alternatus, etc. Basilepta pallidula, etc., Scepticus griseus, Shirahoshizo insidiosus, etc. of the weevil family, Sipalinus gigas, etc., Tomicus (piniperda), Indocryphalus aceris, etc., adults, larvae, and eggs of Rhizopertha dominica, etc .; Hemiptera, such as Cinara todocola, aphid, etc. Adults, larvae, and eggs of Adelges japonicus, etc., Aspidiotus cryptomeriae, etc., Ceroplastes ceriferus, etc. Adults, larvae, and eggs of Pachynematus itoi, etc., Neodiprion sertifer, etc. of the family Metidae, and Dryocosmus kuriohilus, etc .; Diptera, for example Of the family Mosquito Adult larvae, larvae and eggs of Tipula aino, etc., Larix gmelinii, Strobilomyia laricicola, etc., Contarinia inouyei, Contarinia matsusintome, etc .; Arthropoda Spider acarids, such as adults, larvae, and eggs of Oligonichus hondoensis, Oligonichus ununguis, etc .; linear animals, Phytophthora, Nematodes, Parasitaphelenchidae, etc. Bursaphelenchus xylophilus, etc. The compound of the present invention represented by the above formula (1) can also be used to internally or externally parasitize cattle, sheep, goats, horses, pigs, poultry, dogs, cats, and fish that are vertebrates, especially warm-blooded vertebrates. The prevention, treatment or prevention of arthropods, nematodes, trematodes, tapeworms and protozoa of domestic animals or pets. The target animal species include, in addition to the above, rodents such as mice, rats, hamsters, and squirrels, carnivores such as ferrets, and pets or experimental animals such as ducks and pigeons. Specific examples of the pest include the following organisms. Diptera of the order Arthropoda, for example, Tabanus rufidens, Tabanus chrysurus, etc., Musca bezzii, Musca domestica, Musca domestica Stomoxys calcitrans, etc., Gasterophilus intestinalis, etc., Hypoderma bovis, etc., Oestrus ovis, etc. Aldrichina grahami, etc., Megaselia spiracularis, etc., Sepsis punctum, etc., Telmatoscopus albipunctatus), Psychoda alternata, etc., Culex pipiens molestus, Culex pipiens pallens, Anopheles sinensis, Culex pipiens triaeniorhynchus summorosus Mosquitoes (Ades albopictus), adult larvae and eggs such as Simulium iwatense, Prosimulium yezoense, Culicoides schulzei, Culicoides arakawae, etc. Flea orders, such as adult flea (Pulex irritans), dog flea (Ctenocephalides canis), larvae, and eggs; lice, such as Haematopinidae suis, Haematopinidae eurysternus Adults, larvae, and eggs of Damalinia bovis, etc., Linognathus vituli, etc., Menopon gallinae, etc. of arthropods; arthropods Orders of the order Acarina, such as Varroa jacobsoni, Haemaphysalis longicornis, Ixodes ovatus, Boophilus microplus ), Amblyomma testudinarium, etc., Ornithonyssus sylvialum, etc., Dermanyssus gallinae, etc., Demodex phylloides, etc., Adults, larvae, and eggs of Sarcoptes scabiei bovis, Knemidocoptes mutans, etc., Otodectes cynotis, Psoroptes communis, etc. Portal cell Orders of the order Nematodes, such as Hookworm, Swine Kidneyworm, Swine Pneumocystis, Trichomonas, Bovine Intestinal Nodule, etc .; Spodoptera, such as Ascaris suum, Ascaris lumbricoides, etc .; Platymonas trematodes, for example Trematode, deer trematode, lung fluke, Japanese ovarian parasitic trematode, etc .; Ascaris, such as leafy worms, expanded worms, pinworms, square worms, thorn groove worms, round Tapeworms, etc .; Protozoan genus Trichomonas, such as Histomonas, such as Histomonas, Protoflagellates, such as Leishmania, Trypanosoma, etc. Order, such as Giardia, etc., Trichomonas order, such as Trichomonas, etc .; Amoeba order, such as Entamoeba, etc; Class, such as Theilaria, Babesia, etc., late spore subclasses, such as Eimeria, Plasmodium, Toxoplasma, and the like. The compound of the present invention represented by the above formula (1) can also be used to repel pests that cause direct harm or unpleasantness to the human body, or to maintain public health status against pests that transport or spread pathogens. Specific examples of pests include: Lepidoptera of the Arthropoda class, for example, Sphrageidus similis, etc., Kunugia undans, etc. Adult larvae, larvae and eggs of the green moth (Parasa consocia), etc., Artona martini, etc. of the moth family; Coleoptera, such as Xanthochroa waterhousei, etc. , Epicauta gorhani, etc., adults, larvae and eggs of Paederus fuscipes, etc. of the Cryptoceraceae family; Bee order, such as Vespa, Vespa simillima xanthoptera, etc., Brachyponera chinensis, etc., adults, larvae, and eggs of the family Arachnidae (Batozonellus annulatus), etc .; Diptera, such as the mosquitoes infesting A. mosquito ( Armigeres subalbatus), Culicoides nipponensis, etc., Chironomus yoshimatsui, etc., Simulium nikkoense, etc., Hirosia humilis ) Etc. Musca domestica, etc., Fania canicularis, etc., Phormia regina, etc., adults, larvae, etc. of Sarcophaga peregrina, etc. Eggs; adults, larvae, and eggs of the order Flea, such as Pulex irritans, etc .; orders of the order, Blattella germanica, etc. Adults, larvae, and eggs of Periplaneta americana), Periplaneta fuliginosa, Japanese giant salamander (Periplaneta japonica); Orthoptera, such as Diestrammena japonica, Sturgeon (Diestrammena apicalis) and other adults, larvae, and eggs; lice, such as Pediculus humanus humanus, and adults, larvae, and eggs; and Hemiptera, For example, Cimex lectularius, etc., adults, larvae, and eggs of the brown assassin flies (Isyndus obscurus) in the family Falconidae; Collembola, a member of the arthropod phylum near the insect class, for example Hypogast adults, larvae, and eggs such as rura communis; Arthropoda acarina, such as Ixodes persulcatus of the Ixodes family; Ornithonyssus bacoti, etc. , Chelacaropsis moorei, etc., Pyemotes ventricosus, etc., Demodex folliculorum, etc., Dust mite house dust mites (Dermotophagoides pteronyssinus), adults of Sarcoptes scabiei, etc., adults, larvae, and eggs of Trombicula akamushi, etc. of the acarid family; spider order, such as the Japanese red snail Chiracanthium japonicum, Heteropoda venatoria, etc., Spermophora senoculata, Pholcus phalangioides, etc. Adults, larvae and eggs of black fly tigers (Plexippus paykulli), Plexippus adansoni, etc. of Uroctea compactilis, etc .; adults of scorpiones, such as Isometrus europaeus, Larvae and eggs; adults, larvae, and eggs of arthropods, Hymenoptera, such as Scolopendra subspinipes mutilans, Scolopendra subspinipes japonica, etc. Adults, larvae, and eggs of Thereuronema hilgendofi, etc .; adults, larvae, and eggs of the order Amphipoda of the order Arthropoda, for example, Oxidus gracilis of the Chimaruidae; Arthropoda crustaceans, etc. Adults, larvae, and eggs of the Order of the Foot, such as Porcellio scaber; Ornithopoda of the genus Amphiptera, such as Haemadipsa zeylanica japonica; as trichophyton fungi Trichophyton rubrum, Trichophyton mentagrophytes, etc., Candida albicans, etc., Aspergillus fumigatus, etc. as fungi, E. coli (Escherichia coli), Pseudomonas aeruginosa and other Gram-negative fungi, Staphylococcus aur eus) and other Gram-positive fungi. The compound of the present invention represented by the above formula (1) is particularly useful for the control of harmful organisms such as arthropods, gastropods, nematodes, and fungi that damage crops, or natural forests, plantations, and trees or ornamental plants in urban green spaces value. In such a scenario, the compounds of the present invention are such commercially useful preparations and use forms prepared from these preparations, and can also be combined with other active compounds, such as pesticides, or acaricides, nematodes Agents, fungicides, synergists, plant regulators, poison baits or herbicides. As the use form, suspending agents such as hydration agents, granule hydration agents, dry suspension agents, water solvents, emulsions, liquids, oils, water suspension agents, and water opacifiers, capsules, powders, granules, fine suspensions, etc. Granules, baits, lozenges, sprays, aerosols, aerosols, etc. In order to form these dosage forms, various agricultural chemicals previously used in the technical field of agricultural and horticultural agents can be appropriately used. Such an agricultural chemical adjuvant can be used, for example, for the purpose of improving the effect, stabilization, and dispersibility of agricultural and horticultural chemicals. Examples of the pesticide adjuvant include a carrier (diluent), a spreading agent, an emulsifier, a wet spreading agent, a dispersing agent, and a disintegrating agent. Examples of the liquid carrier include water, or aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol, and glycol, ketones such as acetone, amides such as dimethylformamide, and dimethylimide. Rhenium and other fluorenes, methylnaphthalene, cyclohexane, animal and vegetable oils, fatty acids, etc. In addition, as the solid carrier, clay, or kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, gum arabic can be used. Wait. As the emulsifier or dispersant, common surfactants can be used. For example, anionic systems such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkyl phenyl ether, and lauryl betaine can be used. Surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, etc. Also usable are: spreading agents; wet spreading agents such as dialkyl sulfosuccinate; fixatives such as carboxymethyl cellulose and polyvinyl alcohol; disintegrating agents such as sodium lignosulfonate and sodium lauryl sulfate; etc. . Of course, the compound of the present invention may be formulated as an effective ingredient by using one kind or a combination of two or more kinds. In these preparations, the content of the compound of the present invention as an effective ingredient is, for example, 0. 01 ～ 99. 5 mass%, preferably selected from 0. The range of 5 to 90% by mass may be appropriately determined according to various conditions such as the form of the preparation and the method of application. For example, when it is a powder, it may contain about 0. 5 to 20% by mass, preferably 1 to 10% by mass of the active ingredient. When it is a hydrating agent, it may contain about 1 to 90% by mass, preferably 10 to 80% by mass of the active ingredient. It can be manufactured in the form of an emulsion, and can be manufactured in a form containing an effective ingredient of about 1 to 90% by mass, preferably 10 to 40% by mass. In order to prevent and control arthropods, gastropods, nematodes, and fungi, the plants are usually sprayed on the places where damage is caused by these pests, or where the damage may occur. In addition, you can also borrow The soil is treated by whole layer mixing, ditch application, bed soil mixing, slot seedling treatment, planting hole treatment, root treatment, fertilizer application, rice box treatment, water surface application, etc., and the crops are used to absorb the medicine from the roots. In addition, it can also be used by seed impregnation in a chemical, seed coating, seed treatment such as Calper treatment, application of a nutrient solution to a nutrient solution (hydroponic) cultivation, fumigation, or trunk injection. In the case of use, although it varies according to the type or amount of pests, and the type of crops, trees, or cultivated forms or growth states that are targeted, it is usually applied at an effective ingredient amount of 10 acres. . 1 to 1000 g, preferably 1 to 100 g. In order to treat it, when it is a suspending agent such as a hydrating agent, a granular hydrating agent, a dry suspension agent, a water solvent, an emulsion, a liquid agent, an aqueous suspension agent, an aqueous emulsion agent, a capsule, etc., it is diluted with water. It varies depending on the type of plant to be targeted, the cultivation form, and the growth state, but it is usually sufficient to spray the crops or the like at an application rate of 10 to 1,000 liters per 10 acres. In the case of a powder, a spray or an aerosol, a crop or the like may be treated in the state of the preparation. Examples of the application method when the target pest mainly harms plants in the soil, or when the target absorbs an agent to control the target pest, for example, the preparation is diluted with water or applied without dilution. The method of spraying granules on the plant roots or seedbeds for seedling cultivation, the method of spraying granules on the plant roots or seedbeds for seedling cultivation, etc., spraying powder, hydrating agent, granular hydrating agent before sowing or transplanting, Methods for mixing granules with the whole soil, spraying powders, hydration agents, granular hydration agents, granules, fine granules, etc. on planting holes, ditches, etc. before sowing or before planting plants. In the case of hydration agents, granular hydration agents, water solvents, emulsions, liquids, suspensions in water, suspensions in water, etc., capsules, etc., they are diluted with water. Usually only 5 to 500 liters per 10 ares The application amount may be sprayed on the soil surface or poured into the soil in a uniform manner in all areas to be treated, and when it is a powder, granule, fine granule or bait, etc., the state of the preparation is sufficient. It is sufficient to spray on the soil surface in such a manner that it becomes uniform in all the areas to be treated. Spraying or pouring can also be applied around the seeds or crops and trees to be protected from damage. Further, the active ingredients may be mechanically dispersed during the spraying or after the spraying. As a method of applying the rice seedling box, although the dosage form may vary depending on the application period such as application at the time of sowing, application at the greening stage, application at the time of transplantation, etc., as long as it is applied with powder, granule hydrating agent, granule, fine granule, etc. The dosage form is sufficient. It can also be applied by blending with cultivated soil, and can be mixed with cultivated soil, powder, granular hydrating agent, granule or fine granule, for example, mixed with bed soil, mixed with covering soil, and mixed with whole cultivated soil. In addition, it is also possible to apply just by cultivating the soil and various preparations alternately. As a method of applying to a paddy field, generally, solid preparations such as large granules, sachets, granules, and granule hydrates, liquid preparations such as suspensions, and emulsions are sprayed onto the paddy fields in a state of water. In addition, an appropriate preparation may be sprayed or mixed into the soil directly or mixed with a fertilizer or the like when transplanting rice. In addition, it can also be applied labor-savingly with the supply of water by using a medicinal solution such as an emulsion or a suspension because water flowing into a paddy field such as a nozzle or an irrigation device is used. Examples of the method for seed treatment include a method of diluting or undiluted liquid or solid preparations, immersing the seeds in a liquid state to attach and penetrate the agent, and mixing the solid preparation or the liquid preparation with the seeds to make powder. A method of coating treatment to attach the preparation to the surface of the seed, a method of mixing with an adhesive carrier such as a resin and a polymer to coat the seed, and a method of spraying the seed near the seed while transplanting. The "seed" used for the seed treatment refers to the plant body used in the early cultivation of the plant. For example, in addition to seeds, bulbs, tubers, seed potatoes, plant buds, bulbs, bulbs, or cuttings are used for cultivation. Plants for vegetative propagation. In addition, the "soil" or "cultivation carrier" of a plant in the case of application means a support for growing crops, especially a support for rooting, and the material is not particularly limited as long as it is a material that can grow plants It can be so-called soil, seedling mat, water, and the like. Specific materials include, for example, sand, pumice stone, vermiculite, diatomaceous earth, agar, gelatinous substance, polymer substance, rock wool, and glass. Wool, sawdust, bark, etc. As the treatment for transplanting the cultivated plants in the sowing and seedling stage, in addition to the direct treatment of the seeds, it is preferably a perfusion treatment of a liquid medicine or a granule spray treatment for the seedbed for seedling breeding. In addition, it is also preferable to treat the granules at the planting hole or mixed with the cultivation carrier near the transplantation site during colonization. The compound of the present invention represented by the above formula (1) is also valuable for protecting wood (timber, fallen wood, processed wood, storage wood, or structural wood) from insects or fungi such as termites or coleoptera. In such a scenario, it can be controlled by spraying or injecting, pouring, coating oil, emulsion, hydrating agent, sol, spraying powder, granule, etc. on the wood or the surrounding soil. In addition, the oils, emulsions, hydration agents, powders, etc. used in this scene can also be mixed with other active compounds, such as pesticides, acaricides, acaricides, fungicides, repellents or synergists. Exist in the form, in these preparations, the active ingredient compound may contain 0 in total. 0001 to 95% by mass, preferably, may contain 0 when used as an oil, powder or granule. 005 to 10% by mass, when it is an emulsion or a hydrating agent and a sol, may contain 0. 01 to 50% by mass. For the control of arthropods or fungi, every 1 m² The effective ingredient compound meter is sprayed on the soil or wood surface from 0.01 to 100 g. The compound of the present invention represented by the above formula (1) can be used to protect cereals, fruits, fruit of trees, spices, tobacco, and other products when stored in the original state, powdered state, or mixed into the product. Protect from Lepidoptera, Coleoptera, Mites and Fungi. In addition, when storing animal products (skin, wool, wool, feathers, etc.) or plant products (cotton, paper, etc.) in a natural or transformed state, they can also be protected from Lepidoptera, Coleoptera, and clothing Attacks by fish or tadpoles, and furthermore, when storing food such as meat or fish, it can be protected from attacks by Lepidoptera, Coleoptera, Diptera or Mites. In this scenario, spraying of oils, emulsions, hydration agents, powders, etc., setting of resin transpiration agents, treatment of fumigants or aerosols, setting of granules, lozenges, and poisonous baits, and setting of aerosols Spray and other methods for prevention. In addition, these preparations can also exist in the form of a mixture of other active compounds, such as insecticides, acaricides, nematicides, fungicides, repellents or synergists. In these preparations, the active ingredients The compound may contain 0.0001 to 95% by mass in total. The compound of the present invention represented by the above formula (1) is an arthropod or a fungus which directly causes harm to the skin, such as food intake or blood absorption, parasitizing the human body and livestock, spreading diseases of human beings and livestock, or such The disease vectors are valuable in the removal or prevention of arthropods, nematodes, trematodes, tapeworms, protozoa, and arthropods that cause unpleasantness to humans. In such a scenario, the compound of the present invention can be mixed into a small amount of food or feed, etc., or a suitable pharmaceutical composition for oral ingestion, such as a lozenge containing a carrier or a coating material that is permissible on the pharmaceutical , Pills, capsules, plasters, gels, beverages, medicinal feeds, medicinal drinking water, medicated chase, controlled release large pellets, and controlled release devices retained in the gastrointestinal canal. Administration, or transdermal administration in the form of a spray, powder, grease, cream, ointment, cream, lotion, drip agent, shower, shampoo, etc. In order to achieve the effect in such applications, the formulation usually contains 0.0001 to 0.1% by mass, preferably 0.001 to 0.01% by mass, based on the active ingredient compound. Furthermore, as a method of transdermal or local administration, devices (such as collars, necklace pendants, ear tags, etc.) installed on animals to control arthropods locally or systemically can also be used. The specific oral administration method and transdermal administration method when the compound of the present invention represented by the above formula (1) is used as an insect repellent for animals or humans such as livestock or pets will be disclosed, but it is not necessarily Limited to these. In the case of oral administration in the form of medicinal drinking water, the beverage is dissolved or suspended in a suitable non-toxic solvent or water together with a normal bentonite-like suspension or wetting agent or other excipient. Dispersions. Beverages often also contain antifoaming agents. The beverage formula usually contains 0.01 to 1.0% by mass, preferably 0.01 to 0.1% by mass of the active ingredient compound. When it is more ideal for oral administration in the form of a dry individual unit, capsules, pills or lozenges containing specific amounts of active ingredients are usually used. These use forms are produced by diluting the active ingredient with appropriately finely divided diluents, fillers, disintegrating agents and / or binding agents, such as starch, lactose, talc, magnesium stearate, vegetable properties Rubber etc. are blended evenly. The formulation of such a unit can widely change the quality and content of the repellent according to the type of host animal to be treated, the degree of infection, the type of parasite and the weight of the host. When the animal feed is used for administration, it can be dispersed uniformly in the feed or used as a crest and used in the form of pellets. In order to achieve a generally ideal antiparasitic effect, the final feed contains 0.0001 to 0.05% by mass, preferably 0.0005 to 0.01% by mass of an active ingredient compound. Those dissolved or dispersed in a liquid carrier excipient may be administered to the animal by intragastric, intramuscular, intratracheal, or subcutaneous injection instead of orally. For parenteral administration, the active compound is preferably mixed with a suitable vegetable oil such as groundnut oil and cottonseed oil. Such a formulation usually contains the active ingredient compound in an amount of 0.05 to 50% by mass, preferably 0.1 to 5.0% by mass. In addition, it can be administered locally by mixing with a suitable carrier such as dimethylsulfinium or a hydrocarbon solvent. The formulation is applied directly to the external surface of the animal by spraying or direct injection. In addition, the compound of the present invention represented by the above formula (1) may also be in the form of an insect repellent such as arthropods that are directly harmful or arthropods that are vectors of diseases. The environment, heating the smoke by spraying, injecting, pouring, coating, powdering, spraying, fumigants, mosquito killers, self-burning fumigants, chemical reactive aerosols, etc. Fumigants, atomizers, etc., treatment of ULV (Ultra Low Volume), etc., setting of granules, tablets, poisonous baits, or floating powders, granules, etc. Water tanks and other methods of dripping and adding in running or standing water are used. Furthermore, for poisonous moths, which are also agricultural and forest pests, they can be controlled in the same way as above, or for flies, etc., which is mixed into the feed of livestock and mixed with feces. It is also effective for mosquitoes, etc. Methods such as electric mosquito killers flying into the air are also effective. Furthermore, these preparations in the form of use can also exist in the form of a mixture with other active compounds, such as pest control agents, mite control agents, nematode control agents, disease control agents, repellents or synergists. The active ingredient compound contains 0.0001 to 95% by mass in total. The compound of the present invention represented by the above formula (1) may also exist in the form of a mixture with other active compounds. In particular, when used in combination with compounds (insecticides) that have pest control activity, mite control activity, or nematode control activity, it can be used to control pests such as arthropods, gastropods, and nematodes that cause damage to plants. Synergistic effects such as reduction in drug dose can also be expected by expanding the target pests and diseases. Examples of the specific active compound include organophosphorus agents, such as acephate, azonphos-methyl, chlorpyrifos, daizinon, dichlorvos, and dichlorvos. Dimeton-S-methyl, dimethoate, dimethylvinphos, disulfoton, ethion, fenitrothion, fendipine fenthion, isoxathion, marathion, methamidophos, methidathion, monocrotophos, naled, oxideprofos, parathion, Phenthoate, phosalone, pirimiphos-methyl, piridafenthion, profenofos, prothiofos, propaphos, Pyraclofos, salithion, sulprofos, thiometon, tetrachlorvinfos, trichlorphon, vamidothion, etc. ; Carbamates, such as alanycarb, bendiocarb, fuc (b enfuracarb), carbaryl, carbofuran, butyl carbosulfan, ethiofencarb, fenobucarb, furathiocarb, Isoprocarb, methodolyl, metolcarb, pirimicarb, propoxur, thiodicarb, etc .; organochlorines, such as aterin ( aldrin), chlordane, DDT (Dichloro-Diphenyl-Trichloroethane, di-p-chlorophenyltrichloroethane) (p, p'-DDT), endosulfan, lindane, etc .; Pyrethroid-like agents, such as anrinathrin, allethrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cyphenidin (cyphenothrin), cypermethrin, deltamethrin, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, trifluthrin (flufenprox), fluvalinate, furamethrin, halfenprox, imiprothrin , Permethrin, phenothrin, prallethrin, pyrethrins, resmethrin, silafluofen, tefluthrin (permethrin) tefluthrin, tralomethrin, transfluthrin, etc .; neonicotinoids, such as acetamiprid, clothianidin, dinotefran, imidacloprid ), Nitenpyram, thiacloprid, thiamethoxam, etc .; diammonium agents, such as chlorantraniliprore, cyantraniliprore, cyanocloprid Cyclaniliprore, flubenziamid, etc .; phenylpyrazole agents, such as ethiprole, fipronil, acetoprole, pyrofluoprole, flubenzimid Pyriplore, etc .; Nereistoxin agents, such as bensultap, cartap, thiocyclam, thiosultap, etc .; Phenylbenzyl urea or difluorenyl Insect growth inhibitors such as hydrazines, such as chlorfluazuron, diflubenzuron, Flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, bufofezin, cofen Chromafenozide halofenozide, methoxyfenozide, tebufenozide, cyromazine, etc .; juvenile hormone agents, such as diofenolan, fenock fenoxycarb), hydroprene, metoprene, pyriproxyfen, etc .; insecticidal substances produced by microorganisms, such as abatectin, emamectin (emamectin-benzoate), ivermectin, lepimectin, milbemectin, nemadectin, Nikkomycin, polioxin ), Spinetram, spinosad, Bacillus thuringiensis, etc .; insecticidal substances derived from natural materials, such as anabaine, azadiractin, fish Deguelin, fatty acid glyceride (decanolyoctanoylglycerol), hydroxypropyl starch (h ydroxy propyl starch), soy lecithin, nicotine, nornicotine, oreic acid sodium salt, petroleum oil, propylene glycol monolaurate ), Rapeseed oil (rape oil), rotenone, sorbitan fatty acid ester (sorbitan fatty acid ester), starch (starch), etc .; as other pesticides, for example: aidpyropen, kefir (chlorfenapyr), diafenthiuron, DBEDC (Dodecylbenzenesulphonic acidbisethylenediamine copper [II] salt), flonicamid, flometoquin, acetamiprid Amine (flufenerim), flupyradifurone, hydramethylnon, indoxacarb, metaflumizone, metaaldehyde, nicotin sulfate, nicotin sulfate Pymetrozine, pyridalyl, pyrifluquinqzon, spirotetramat, sulfoxaflor, tolfenpyrad, triazamate, etc .; acaricides For example Mite (acequinocyl), amidoflumet, amitraz, azocyclotin, benzoximate, bifenazate, binapacryl, bromomite (bromopropylate), chinomethionat, clofentezine, cyenopyrafen, cyflumetofen, cyhexatin, dicofol, dicofol (dienochlor), ethoxazole, fenazaflor, fenazaquin, fenbutatin oxide, fenothiocarb, fenpyroximate, pyrimicarb (fluacrypyrim), hexythiazox, pirimidifen, polynactins, propargite, pyflubumide, pyridaben, spirodiclofen, snail Spiromesifen, tebufenpyrad, tetradifon, etc .; nematicides, such as aluminum phosphide, benclothiaz, cadusafos, puvol Pine (ethoprophos), fluensulfone, fosthiazate, furfural, Imicyafos, levamisol hydrochloride, mesulfenfos, metam-ammonium, methyl isothiocyanate, morentair tartrate (moranteltartarate), oxamyl, thioxazafen, etc .; poisonous baits, such as chlorphacinone, coumatetralyl, diphacinone, sodium fluoracetate, warfarin )Wait. The compound of the present invention represented by the above formula (1) may also exist in the form of a mixture with active compounds other than compounds having pest control activity, mite control activity, and nematode control activity. In order to control the disease and / or weeds generated during use, it is used in combination with a compound that has fungicidal activity, or herbicidal activity, or plant growth regulating activity, so that it can be expected to reduce the labor and reduce the amount of medicine. Effect, etc. In addition, when used in combination with a repellent or synergist, a more effective control effect such as a synergistic effect can be expected. Examples of the specific active compound include disease control agents such as DD (1,3-dichloropropene), acidified benzothiadiazole-S-methyl, and aldimorph. , Ametoctradin, amisulbrom, andoprim, anilazine, azaconazole, azoxystrobin, basic copper sulfate copper sulfate), benodanil, benomyl, benthiavalicarb-isopropyl, benthiazole, bitertanol, bixafen, exterminator Blasticidin S, boscalid, bromuconazole, calcium carbonate, buthiobate, calcium polysulfide, captafol , Captan, carbendazim, carboxin, carpropamid, chinomethionat, chlorfenazole, chloroneb, Chloropicrin, chlorothalonil, chlozolinate, DBEDC (complex of bis (ethylenediamine) copper-bis- (dodecylbenzenesulfonic acid), bis (dodecylbenzenesulfonic acid) bis (ethylenediamine) copper compound), copper hydroxide, copper nonylphenol sulfonate (copper nonylphenol sulfonate, copper oxychloride, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, Myron (dazomet), diclobutrazol, dichlofluanid, dichlone, dilocymet, diclomezine, diethofencarb, Difenoconazole, diflumetorim, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dithane-stainless, Dithianon, dodine, echlomezole, edifenphos, enestrobin, epoxiconazole, etaconazole, thiazole Ethaboxam, extract from mushroom, Fanshatong famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanol, seed dressing (fenpiclonil), fenpropidin, fenpyrazamine, ferimzone, fluazinam, flumetover, flumorph, fluorine Fluopicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, fluoxan ( flusulfamide, flutolanil, fluxapyroxad, folpet, fosetyl-AL, fthalide, fuberidazole, protective Fludioxonil, flusilazole, flutianil, flutriafol, furametpyr, furconazole, guazatine, ficili ( hexaconazole, hydroxyioxazole, hymexazol, imazalil, imazalil sulfa te), imibenconazole, iminoctadine acetate, iminoctadine-DBS, ipconazole, iprobenfos, iproton (iprodione), iprovalicarb, isofetamid, isoprothiolane, isopyrazam, isotianil, kasugamycin , Kresoxim-methyl, mancozeb, mandipropamid, maneb, manzeb, mepanipyrim, mepenipine mepronil, metalaxyl, metam-ammonium, metam-sodium, metconazole, methasulfocarb, methyl bromide, isopropyl Methyl isothiocyanate, metominostrobin, mefenfenone, mildiomycin, myclobutanil, nickel dimethyldithiocarbamate, nirimer (nuarimol), orysastrobin, oxadixyl, oxathiapi prolin), organic copper (oxine-copper), oxolinic acid, oxpoconazole fumarate, oxycarboxin, oxytetracycline, pebulate ), Pefurazoate, penconazole, pencycuron, penflufen, penthiopyrad, picarbutrazox, picoxystrobin, powdery mildew (piperalin), polycarbamate, polyoxin-B, polyoxins, potassium hydrogen carbonate, probenazole, prochloraz ), Promethmidone, propamocarb, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin ), Pyrametostrobin, pyroxystrobin, pyrazophos, pyribencarb, pyridinitril, pyrifenox, pyrimethanil ), Pyriofenone, pyroquil on), quinoxyfen, quintozene, sedaxane, silver, simeconazole, sodium hydrogen carbonate, sodium hypochlorite hypochlorite, spiroxamine, streptomycin, sulfur, tebfloquin, tebuconazole, tecloftalam, terbinafine (terbinafine), tetraconazole, thiabendazole, thiadiazin, thifluzamide, thiophanate, thiophanate-methyl, defendi ( thiram, tiadinil, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, three Tricyclopyricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, ene Uniconazole-P, validamycin (-A), vinclozolin ), Zarilamid, zinc sulfate, zineb, ziram, zoxamide, and the like. Examples of the compound having herbicidal activity include aclofen, acifluofen-sodium, alachlor, alloxydim, and amidcarbazone. , Amidosulfuron, anilofos, asulam, atrazine, azimsulfuron, benfuresate, bensulfuron (bensulfuron-methyl), bentazone, benthiocarb, benzobicyclon, benzofenap, bialaphos, bifenox, Bromobutide, bromoxynil, butamifos, cafenstrole, calcium peroxide, carbetamide, etsulfuron cinosulfuron, clomeprop, cyclosulfamuron, cyhalofop-butyl, daimuron, desmedipham, diclofop-methyl , Diflufenican, dimefuron, dimethametryn, dinoterb, Diquat, diuron, esprocarb, ethiozin, ethofumesate, ethoxysulfuron, ethoxysulfuron etobenzanid), fenoxaprop-P-ethyl, fentrazamide, flucarbazone, flufenacet, flurtamone, oxalic acid Fluthiacet-methyl, foramsulfuron, glufosinate-ammonium, glyphosate-isopropyl amine, glyphosate-trimesium, glyphosate Imazapyr, imazosulfuron, indanofan, iodosufluron, ioxynil-octanoate, isoproturon, bisbenzopyrazole (isoxadifen), isoxaflutole, lactofen, linuron, mefenacet, mesosulfuron, metamitron ), Methabenzthiazuron, metosulam, metribuzin, napropamide, nebur on), oxadiargyl, oxadiazon, oxaziclomefone, paraquat, pendimethalin, pentoxazone, phenanthrene (phenmedipham), pretilachlor, propoxycarbazone, prosulfocarb, pyraclonil, pyraflufen-ethyl, pyrazolate, Pyrazosulfuron-ethyl, piributicarb, pyriftalid, pyriminobac-methyl, quizalofop-ethyl, sethoxydim, western Simazine, sulcotrion, sulfentrazone, thenylchlor, triaziflam, tribufos, and the like. In addition, as a compound having a plant growth regulating effect, for example, it may be used with 1-naphthylacetic acid, 4-CPA, 6-benzylaminopurine, butralin , Calcium chloride, calcium formate, calcium peroxide, calcium sulfate, chlormequat chloride, choline, cyanamide , Cyclanilide, daminozide, decyl alcohol, dichjoprop, ethephon, ethychlozate, furazylol ( flurprimidol, forclorfenuron, gibberellic acid, indolebutyric acid, maleic hydrazide potassium salt, mefenpyr, mepiperium (mepiquat chloride), 8-hydroxyquinoline sulfate (oxine sulfate, 8-hydroxyquinoline sulfate), paclobutrazol, paraffin, prohexadione-calcium, prohydrojasmon, thiophene Thidiazuron, trinex apac), uniconazole-P, wax and the like are used in combination. Examples include: repellents, such as capsaicin, carane-3,4-diol, citronellal, deet, phthalic acid Dimethyl phthalate, hinokitiol, limonene, linalool, menthol, menthone, naphthalene, thiram, etc .; Synergists, such as methylenedioxynaphthalene, naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentyl Alkynyl pentynyl phthalimide, phenyl salioxon, piperonil butoxide, safrole, sesamex, sesamin, sulfoxide , Triphenyl phosphate (triphenyl phosphate), synergistic alkyne (verbutin), etc. The compounds of the present invention can be used as biological pesticides with, for example, Cytoplasmic polyhedrosis virus (CPV), Entomopox virus (EPV), Granulosis virus (GV), and nuclear polyhedrosis virus. (Nuclear polyhedrosis virus, NPV) and other viral preparations, used as Beauveria bassiana, Beauveria brongniartii, Monacrosporium phymatophagum, rose smoke Paecilomyces fumosoroseus, Pasteuria penetrans, Steinernema carpocapsae, Steinernema glaseri, Steinernema kushidai, Verticillium lecanii, etc. Nematode microbial pesticides, used as Agrobacterium radiobactor, Bacillus subtilis, Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02 (Pseudomonas CAB-02), Pseudomonas fluorescens, Talaromyce s), Trichoderma atroviride, Trichoderma lignorum, and other fungicides; microbial pesticides; Xanthomonas campestris; and other biological pesticides. Use and expect the same effect. Furthermore, it can also be used as a biological pesticide with, for example, Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, and Aphis pipiens mosquito. (Aphidoletes aphidimyza), Chrysoperia carnea, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Franklinothrips vespiformis, Harmonia axyridis, Hemiptarsenus varicornis, Neochrysocharis formosa, Orius sauteri, Orius strigicollis, Chile Natural enemy creatures such as Phytoseiulus persimilis, Pilophorus typicus, Piocoris varius, codlelure, cuelure, geraniol , Gyptol, liblure, looplure, methyl eugenol, orfralure, cis-7-icos-11-one (peachflure) Pheromone, phycilure, 14-methyl-1-octadecene (pyrimalure), turpentine and other pheromone agents are used in combination. [Examples] Hereinafter, the present invention will be described in detail by further describing examples, preparation examples, and test examples, but the scope of the present invention is not limited by these examples, preparation examples, and test examples. Example 1. 1-1:2,5- Difluoro -4- [4- ( Trifluoromethyl ) Piperidine -1- base ] Benzonitrile ( Compound number: B-1) Synthesis: To a solution of 2,4,5-trifluorobenzonitrile (1.57 g) in N, N-dimethylformamide (25 ml) was added 4-trifluoromethylpiperidine (1.68 g) and potassium carbonate ( 1.65 g). After the reaction solution was stirred at room temperature for 15 minutes, water (50 ml) and ethyl acetate (50 ml) were added to separate the organic layer, and the organic layer was further washed with water. Utilize MgSO₄ After the organic layer was dried, the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.66 g (mp 57.5-59.5 ° C) of 2,5-difluoro-4- (4- (trifluoromethyl) piperidin-1-yl) benzyl Nitrile. 1-2:5- fluorine -2- Propylthio -4- [4- ( Trifluoromethyl ) Piperidine -1- base ] Benzonitrile ( Compound number: A-1) Synthesis: N-methyl- of 2,5-difluoro-4- (4- (trifluoromethyl) piperidin-1-yl) benzonitrile (B-1) (0.87 g) synthesized in 1-1 To a solution of 2-pyrrolidone (10 ml) was added sodium 1-propanethiolate (0.35 g), and the mixture was stirred at 140 ° C for 5 hours. After the reaction solution was cooled to room temperature, water (50 ml) and ethyl acetate (30 ml) were added to separate the organic layer, and the organic layer was further washed with water. Utilize MgSO₄ After the organic layer was dried, the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.38 g (mp 76-78 ° C) of 5-fluoro-2-propylthio-4- [4- (trifluoromethyl) piperidin-1-yl ] Benzonitrile. 1-3:5- fluorine -2-( Propylsulfinyl ) -4- [4- ( Trifluoromethyl ) Piperidine -1- base ] Benzonitrile ( Compound number: A-2) Synthesis: 5-Fluoro-2-propylthio-4- [4- (trifluoromethyl) piperidin-1-yl] benzonitrile (A-1) (0.70 g) synthesized in 1-2 was dissolved in chloroform (7 ml), 70% m-chloroperbenzoic acid (0.67 g) was added at room temperature, and the reaction solution was stirred at room temperature for 1 hour. After the reaction solution was stirred at room temperature for 30 minutes, saturated sodium bicarbonate water (20 ml) and chloroform (10 ml) were added, the organic layer was separated, and the organic layer was further washed with water. Utilize MgSO₄ After the organic layer was dried, the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.48 g (mp 98.6-110 ° C) of 5-fluoro-2- (propylsulfinamidinyl) -4- [4- (trifluoromethyl) piperazine Pyridin-1-yl] benzonitrile. Example 2. 2-1:2,5- Difluoro -4- [4- ( Trifluoromethyl ) Piperidine -1- base ] Benzaldehyde ( Compound number: B-2) Synthesis: To a solution of 2,4,5-trifluorobenzaldehyde (0.80 g, 5.00 mmol) in N, N-dimethylformamide (DMF, 10 mL) was added 4- (trifluoromethyl) piperidine (0.77 g, 5.00 mmol), potassium carbonate (1.04 g, 5.00 × 1.5 mmol), stirred at room temperature for 3 hours, and further heated and stirred at 60 ° C. for 3 hours. Water was added to the reaction solution, and extraction was performed with ethyl acetate. The obtained organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.30 g (oil) of 2,5-difluoro-4- [4- (trifluoromethyl) piperidin-1-yl] benzaldehyde. 2-2:5- fluorine -2- (2,2,2- Trifluoroethylthio ) -4- [4- ( Trifluoromethyl ) Piperidine -1- base ] Benzaldehyde ( Compound number: A-64) Synthesis: A solution of 2,5-difluoro-4- [4- (trifluoromethyl) piperidin-1-yl] benzaldehyde (B-2) (1.09 g) synthesized in 2-1 in DMF (5.5 mL) A 20% -2,2,2-trifluoroethanethiol / DMF solution (2.39 g) was added thereto, and the mixture was heated and stirred at 80 ° C for 6 hours. 1N-hydrochloric acid was added to the reaction solution, and extraction was performed with ethyl acetate. The obtained organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.24 g (oil) of 5-fluoro-2- (2,2,2-trifluoroethylthio) -4- [4- (trifluoro Methyl) piperidin-1-yl] benzaldehyde. 2-3:5- fluorine -2- (2,2,2- Trifluoroethylthio ) -4- [4- ( Trifluoromethyl ) Piperidine -1- base ] Benzyl alcohol ( Compound number: A-70) Synthesis: 5-Fluoro-2- (2,2,2-trifluoroethylthio) -4- [4- (trifluoromethyl) piperidin-1-yl] benzaldehyde (A- 64) (1.24 g) in ethanol (20 mL) was added with sodium borohydride (0.06 g), and the mixture was stirred at room temperature for 4 hours. Ethyl acetate was added to the reaction solution, and the mixture was acidified with 1N-hydrochloric acid, and then the organic layer was extracted. The obtained organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.12 g (mp 96-98 ° C) of 5-fluoro-2- (2,2,2-trifluoroethylthio) -4- [4- (tri Fluoromethyl) piperidin-1-yl] benzyl alcohol. 2-4:1- fluorine -3- methyl -4- (2,2,2- Trifluoroethylthio ) -6- [4- ( Trifluoromethyl ) Piperidine -1- base ] benzene ( Compound number: A-27) Synthesis: 5-Fluoro-2- (2,2,2-trifluoroethylthio) -4- [4- (trifluoromethyl) piperidin-1-yl] benzyl alcohol (A- To a solution of 70) (0.56 g) in dichloromethane (7 mL) was added thionyl chloride (0.17 g), and the mixture was stirred at room temperature for 4 hours. The reaction solution was poured into water and the organic layer was extracted. The obtained organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The desiccant was separated by filtration, and the solvent was distilled off under reduced pressure to obtain 0.59 g (oil) of 1-chloromethyl-3-fluoro-6- (2,2,2-trifluoroethylthio) -4- [4- (trifluoromethyl) piperidin-1-yl] benzene. The obtained 1-chloromethyl-3-fluoro-6- (2,2,2-trifluoroethylthio) -4- [4- (trifluoromethyl) piperidin-1-yl] benzene was not subjected to After purification, DMSO (Dimethylsulfoxide, dimethyl methylene maple) (8 mL) was added, and sodium borohydride (0.11 g, 1.43 × 2 mmol) was added to the reaction solution at room temperature, followed by stirring for 1 hour. Ethyl acetate was added to the reaction solution, and the mixture was acidified with 1N-hydrochloric acid, and then the organic layer was extracted. The obtained organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.44 g (oil) of 1-fluoro-3-methyl-4- (2,2,2-trifluoroethylthio) -6- [ 4- (trifluoromethyl) piperidin-1-yl] benzene. 2-5:1- fluorine -3- methyl -4- (2,2,2- Trifluoroethylsulfinyl ) -6- [4- ( Trifluoromethyl ) Piperidine -1- base ] benzene ( Compound number: A-28) Synthesis: 1-fluoro-3-methyl-4- (2,2,2-trifluoroethylthio) -6- [4- (trifluoromethyl) piperidin-1-yl] synthesized in 2-4 To a solution of benzene (A-27) (0.29 g) in chloroform (12 mL) was added 70% m-chloroperbenzoic acid (0.18 g), and the mixture was stirred at room temperature for 1 hour. The reaction solution was poured into saturated sodium bicarbonate water and the organic layer was extracted. The obtained organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.16 g (mp 116-118 ° C) of 1-fluoro-3-methyl-4- (2,2,2-trifluoroethylsulfinyl sulfenyl). -6- [4- (trifluoromethyl) piperidin-1-yl] benzene. Example 3. 3-1:2-( Cyclopropylmethylthio ) -5- fluorine -4- [4- ( Trifluoromethyl ) Piperidine -1- base ] Benzonitrile ( Compound number: A-19) Synthesis: Dissolve 2,5-difluoro-4- (4- (trifluoromethyl) piperidin-1-yl) benzonitrile (B-1) (1.16 g) in DMF (20 ml) and add sulfur Sodium hydride n hydrate (0.45 g) was stirred at 80 ° C for 3 hours. After allowing to cool to 70 ° C. or lower, cyclopropylmethyl iodide (0.87 g) and potassium carbonate (0.77 g) were added and stirred for 15 minutes, and then heated to 80 ° C. and stirred for 4 hours. After leaving to cool, it was released into water (100 ml), extracted with ethyl acetate (50 ml), and the organic layer was washed 5 times with brine (50 ml). The residue was dried with sodium sulfate, the ethyl acetate was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 2- (Cyclopropylmethylthio ) -5-fluoro-4- [4- (trifluoromethyl) piperidin-1-yl] benzonitrile 0.89 g (oil). 3-2:2-( Cyclopropylmethylsulfinyl ) -5- fluorine -4- [4- ( Trifluoromethyl ) Piperidine -1- base ] Benzonitrile ( Compound number: A-20) Synthesis: Synthesis of 3-1 from 2- (Cyclopropylmethylthio ) -5-fluoro-4- [4- (trifluoromethyl) piperidin-1-yl] benzonitrile (A-19) (0.36 g) was dissolved in chloroform (5 ml) and added at room temperature 70% m-chloroperbenzoic acid (0.24 g), and the reaction solution was stirred at room temperature overnight. An aqueous solution of sodium carbonate (10 ml) and chloroform (5 ml) were added, the organic layer was separated, and the organic layer was further washed with water. Utilize MgSO₄ After the organic layer was dried, the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 5-fluoro-2- (Cyclopropylmethyl Sulfinylene) -4- [4- (trifluoromethyl) piperidin-1-yl] benzonitrile 0.13 g (m.p. 106-108 ° C). Example 4.1- fluorine -3- methyl -4- (2,2,2- Trifluoroethylsulfinyl ) -6- [4- ( Trifluoromethyl ) Piperidine -1- base ] benzene ( Compound number: A-28) Synthesis: 1-fluoro-3-methyl-4- (2,2,2-trifluoroethylthio) -6- [4- (trifluoromethyl) piperidine- synthesized in Example 2 at room temperature To a solution of 1-yl] benzene (A-27: 18.3 g) in methanol (140 mL) was added 35% hydrogen hydrogen peroxide (4.75 g) and sodium tungstate dihydrate (5 mol%), and the temperature was maintained at this temperature. Stir for 6 hours. The reaction solution was poured into water (300 mL), and stirred at room temperature for 0.5 hours. The precipitated crude product was collected by filtration, poured into a petri dish, and air-dried in a draw ratio to obtain 1-fluoro-3-methyl-4- (2,2,2-trifluoroethylsulfinylsulfonium Group) -6- [4- (trifluoromethyl) piperidin-1-yl] benzene 18.7 g (mp 116-118 ° C). Example 5.1- fluorine -3- Methoxymethyl -4- (2,2,2- Trifluoroethylthio ) -6- [4- ( Trifluoromethyl ) Piperidine -1- base ] benzene ( Compound number: A-84) Synthesis: Incorrectly, 5-fluoro-2- (2,2,2-trifluoroethylthio) -4- [4- (trifluoromethyl) piperidine- 1-yl] benzyl alcohol (A-70: 4.10 g) adjusted to obtain 1-chloromethyl-3-fluoro-6- (2,2,2-trifluoroethylthio) -4- [4- (Trifluoromethyl) piperidin-1-yl] benzene was purified, and methanol (50 ml) and potassium carbonate (1.64 g) were added at room temperature, followed by stirring at room temperature for 3 hours. After the reaction solution was concentrated, water and ethyl acetate were added. After the organic layer was dried with anhydrous sodium sulfate, the desiccant was separated by filtration, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1-fluoro-3-methoxymethyl-4- (2,2,2-trifluoroethylthio) -6- [4- ( Trifluoromethyl) piperidin-1-yl] benzene 2.74 g (oil). Example 6.1- fluorine -3- Methoxymethyl -4- (2,2,2- Trifluoroethylsulfinyl ) -6- [4- ( Trifluoromethyl ) Piperidine -1- base ] benzene ( Compound number: A-85) Synthesis: In the same manner as in Example 4, 1-fluoro-3-methoxymethyl-4- (2,2,2-trifluoroethylthio) -6- [4- (trifluoromethyl) piperidine -1-yl] benzene (compound number: A-84) yields 1-fluoro-3-methoxymethyl-4- (2,2,2-trifluoroethylsulfinyl) in 84% yield -6- [4- (trifluoromethyl) piperidin-1-yl] benzene (mp 134-136 ° C). For compounds produced in the same manner as in the above examples,¹ H-NMR data are shown in Table 3 below. table 3 Several formulation examples are listed below to specifically describe the formulations containing the compound of the present invention, but the compounds, auxiliary components, and their added amounts of the present invention are of course not limited to the following formulation examples. In addition, in a formulation example, a part represents a mass part. Formulation Example 1 Emulsion The compound of the present invention (10 parts), xylene (60 parts), N-methyl-2-pyrrolidone (20 parts), Sorpol 3005X (nonionic surfactant and anionic interfacial activity A mixture of agents, Toho Chemical Industry Co., Ltd. (trade name) (10 parts) was uniformly mixed and dissolved to obtain an emulsion. Formulation Example 2 Hydrating Agent-1 The compound of the present invention (20 parts), Nipsil NS-K (white carbon, TOSOH SILICA Co., Ltd., trade name) (10 parts), Kaolin Clay (Kaolin, Takehara Chemical Industry) Co., Ltd., trade name) (60 parts), SAN-X P-252 (sodium lignin sulfonate, NIPPON PAPER Chemicals Co., Ltd., trade name) (5 parts), and Lunox P-65L (alkyl allyl group) Sulfonate, Toho Chemical Industry Co., Ltd. (trade name) (5 parts) were uniformly mixed and pulverized to obtain a hydrating agent. Formulation Example 3 Hydrating Agent-2 The compound of the present invention (20 parts), Nipsil NS-K (white carbon, TOSOH SILICA Co., Ltd., trade name) (20 parts), Kaolin Clay (50 parts), Lunox 1000C (naphthalene sulfonate condensate, Toho Chemical Industry Co., Ltd., trade name) (5 parts) and Sorpol 5276 (non-ionic surfactant, Toho Chemical Industry Co., Ltd., trade name) (5 parts) uniformly Mix and pulverize to obtain a hydrating agent. Formulation Example 4 Water Solvent-1 The compound of the present invention (20 parts), Lunox P-65L (alkyl allyl sulfonate, Toho Chemical Industry Co., Ltd., trade name) (3 parts), and a water-soluble carrier ( Potassium chloride (77 parts) was uniformly mixed and pulverized to obtain an aqueous solvent. Formulation Example 5 Water Solvent-2 The compound of the present invention (50 parts), New Kargen BX-C (sodium alkylnaphthalene sulfonate, manufactured by Takemoto Oils and Fats, trade name) (5 parts), silicon dioxide (2 parts), A water-soluble carrier (43 parts) was uniformly mixed and pulverized to obtain an aqueous solvent. Formulation Example 6 Suspension Agent-1 The compound of the present invention (20 parts) was dispersed in propylene glycol (5 parts) and Sorpol 7933 (anionic surfactant, Toho Chemical Industry Co., Ltd., trade name) (5 parts) previously mixed. And water (50 parts) to prepare a slurry-like mixture. Then, the slurry-like mixture was wet-pulverized using a bead mill (Shinmaru Enterprises), and then xanthan gum (0.2 parts) was added beforehand. The resultant was mixed and dispersed in water (19.8 parts) to obtain a suspending agent. Preparation Example 7 Suspension Agent-2 A compound of the present invention (20 parts), New Kargen FS-26 (a mixture of dioctyl sulfosuccinate and polyoxyethylene tristyryl phenyl ether), Takemoto Oil Co., Ltd., product Name) (5 parts), propylene glycol (8 parts), and water (50 parts) were mixed, and the slurry-like mixture was wet-pulverized using a bead mill (Shinmaru Enterprises). Then, xanthan gum (0.2 parts) was sufficiently mixed and dispersed in water (16.8 parts) to prepare a gel, and the pulverized slurry was sufficiently mixed to obtain a suspending agent. Formulation Example 8 EW-1 Compound (20 parts) of the present invention, Sorpol CA-42 (non-ionic active agent, Toho Chemical Industry Co., Ltd., trade name) (15 parts) and preservative PROXEL GX-L (0.1 parts) ) After mixing and homogenizing, water (59.6 parts) was slowly added while stirring to obtain a dispersion. To the obtained dispersion, an antifoaming agent ANTIFOAM E-20 (emulsion-type modified silicone, Kao Corporation, trade name) (0.1 parts) was added, and xanthan gum dispersed in propylene glycol (5.0 parts) was added. (0.2 parts) to obtain an emulsion preparation (phase inversion emulsification method). Formulation Example 9 EW-2 The compound (10 parts) of the present invention was dissolved in xylene (10 parts), and the surfactant RHEODOL 430V (polyoxyethylene sorbitol tetraoleate, Kao Corporation, product Name) (24 parts) were mixed. To water (50.6 parts) was added the obtained solution, an antifoaming agent ANTIFOAM E-20 (emulsion-type modified silicone, Kao Corporation, trade name) (0.1 parts), and a preservative PROXEL GX-L (0.1 Parts), dispersed using a homogenizer, and added xanthan gum (0.2 parts) dispersed in propylene glycol (5.0 parts) to obtain an emulsion preparation (mechanical emulsification method). Formulation Example 10 ME Agent-1 The compound of the present invention (0.01 part) and Sorpol CA-42 (non-ionic active agent, Toho Chemical Industry Co., Ltd., trade name) (0.1 part) were mixed and homogenized, while stirring. Water (99.79 parts) was added slowly. A preservative PROXEL GX-L (0.1 parts) was added to the dispersion to obtain a microemulsion. Formulation Example 11 ME Agent-2 A compound of the present invention (10 parts) and New Kargen D-945 (polyoxyethylene (20 mol) sorbitan monooleate, bamboo oil fat (stock), trade name) (20 Parts) After mixing and homogenizing, water (69.9 parts) was slowly added while stirring. A preservative PROXEL GX-L (0.1 parts) was added to the dispersion to obtain a microemulsion. Formulation Example 12 ME Agent-3 The compound (0.01 part) of the present invention was dissolved in Solvesso 200 (0.08 part) and New Kargen ST-30 (polyoxyethylene aryl phenyl ether formaldehyde condensate, polyoxyalkylene aryl group) Mixture of phenyl ether, alkylbenzene sulfonate, and xylene, bamboo oil (stock), trade name) (0.12 parts), mix with the surfactant and homogenize, and slowly add water while stirring ( 99.69). A preservative PROXEL GX-L (0.1 parts) was added to the dispersion to obtain a microemulsion. Formulation Example 13 Granules-1 The compound (5 parts), bentonite (30 parts), clay (60 parts), and sodium lignosulfonate (5 parts) of the present invention were uniformly pulverized and mixed, and water was added to fully blend them. Then, it extruded and granulated, and dried and granulated to obtain granules. Formulation Example 14 Granules-2 After adding silica sand (90 parts) to a rolling granulator, water was added, and the compound of the present invention (5 parts) and sodium lignin sulfonate (4 parts) were pulverized and mixed in advance. , Polyvinyl alcohol (PVA) (0.5 part) and white carbon (0.5 part), after coating, drying and granulating to obtain granules. Formulation Example 15 Granules-3 ISHIKAWALITE (89 parts) was added to a rolling type granulator, and after water was added, the compound of the present invention (5 parts), sodium lignosulfonate (3 parts), and Dioctyl sodium sulfosuccinate (0.5 parts), POE (polyoxyethylene, polyoxyethylene) styryl phenyl ether (2 parts) and polyvinyl alcohol (PVA) (0.5 parts), after coating, drying and granulating And granules were obtained. Formulation Example 16 Microparticles-1 The compound (2 parts) of the present invention was diluted with a solvent, and the diluted solution was sprayed and mixed with pumice (98 parts) as an extender. The obtained granular composition was dried and then sieved to obtain fine particles. Formulation Example 17 Microparticles-2 The compound (5 parts) of the present invention was pulverized by air milling or mechanochemical pulverization as necessary. After the powdery raw material was uniformly mixed with silica sand (85 parts) as an extender, the mixture was sprayed with Toxanon GR-31A (10 parts), a binder diluted with a solvent, and mixed to obtain a granular form. After the composition is dried, it is sieved to obtain fine particles. Formulation Example 18 Powder To the compound (5 parts) of the present invention, white carbon (5 parts) and clay (Japanese Talc (trade name)) (90 parts) were uniformly mixed and pulverized to obtain a powder. Formulation Example 19 DL powder To the compound (5 parts) of the present invention, propylene glycol (0.5 part) and DL clay (94.5 parts) were uniformly mixed and pulverized to obtain a powder. Formulation Example 20 A seed-coated powder was prepared by mixing the compound of the present invention (10 parts), sodium lignin sulfonate (6 parts), polyvinyl alcohol (PVA) (1 part), and clay (Japanese Talc (stock) trade name) ( 83 parts) uniformly mix the pulverized powder and the previously wetted seeds, and air-dry them to obtain coated seeds. Specific examples are given below to explain the effects and usefulness of the compounds of the present invention. The compound used for comparison is a compound represented by the following formula.Comparative agent A (22-11 described in International Publication No. 2006/087162) Test Example 1: Density inhibition test on Tetranychus urticae A hole in the center (diameter of a 430 ml capacity polyethylene cup lid with water added) 5 mm). From the hole of the lid, insert absorbent cotton with a width of about 1 cm and a length of about 14 cm by immersing in water in the cup, and then put about 8.0 cm square of absorbent cotton on the absorbent cotton. On the absorbent cotton that has been replenished with water in the cup in this way, place two leaf discs (diameter 2 cm) made of primary bean leaves with the back side of the leaf facing up, and inoculate two spots on the disc. Five female adult spider mites. The cup was placed in an acrylic cylinder having a height of 45 cm and a diameter of 12 cm, and an air brush was used to spray 2.0 ml per cup of a water dilution solution (500 ppm) of the emulsion prepared according to Formulation Example 1 (1 concentration, Repeat 1 time). After spraying, keep it in a constant temperature room at 25 ° C. After 7 days of treatment, 100 (density suppression rate: 100%), 95 (density suppression rate: 99-95%), 80 (density suppression rate: 94-80%), 50 (density suppression rate: 79-50%), Five stages of 0 (density inhibition rate: less than 50%) were evaluated for the density inhibition effect of the next generation on the eggs laid by the adult, and based on the results, the density inhibition rate of the next generation was calculated using the following formula. Next generation density suppression rate = (A × 100 + B × 95 + C × 80 + D × 50) / (A + B + C + D + E) where A is the number of leaf discs of 100, B is the number of leaf discs of 95, C is the number of leaf discs of 80, and D is The number of leaf discs of 50, E is the number of leaf discs of 0. As a result, compound numbers A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-9, A-10, A-11, A-12, A- 13, A-14, A-15, A-16, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-31, A-32, A-33, A-34, A-35, A-36, A-39, A-40, A-41, A-42, A-43, A- 44, A-60, A-61, A-62, A-64, A-70, A-71, A-72, A-73, A-73, A-74, A-76, A-77, A-78, A-79, A-80, A-83, A-84, A-85, A-86, A-88, A-96, A-97, A-114, A-115, A- 118, A-123, A-124, A-125, A-126, A-128, A-129, A-130, A-131, A-132, A-133, A-134, A-136, A-137, A-138, A-139, A-140, A-141, A-142, A-149, A-155, A-161, A-164, A-165, A-166, A- The compounds of the present invention of 167, A-171, A-172, A-174, A-175, and A-180 showed a density inhibition rate of 100%. On the other hand, Comparative Agent A had a density inhibition rate of 0%. Test Example 2: Adult insecticidal test against the full-claw mite citrus A polyethylene cup with a capacity of 430 ml added with water was capped with a hole (diameter 5 mm) in the center. From the hole of the lid, insert absorbent cotton with a width of about 1 cm and a length of about 14 cm by immersing in water in the cup, and then put about 8.0 cm square of absorbent cotton on the absorbent cotton. On the absorbent cotton that has been replenished with water in the cup in this way, 2 sheet discs (2 cm in diameter) made of fully expanded leaves of citrus are placed, and 6 adult females of the whole citrus mite mite are inoculated on the disc. . The cup was placed in an acrylic cylinder having a height of 45 cm and a diameter of 12 cm, and an air brush was used to spray 2.0 ml per cup of a water dilution solution (500 ppm) of the emulsion prepared according to Formulation Example 1 (1 concentration, Repeat 1 time). After spraying, keep it in a constant temperature room at 25 ° C. After 4 days of treatment, the life and death and knockdown of adults were investigated under binoculars. The knockdown insects were considered dead and the mite killing rate was calculated (%) [(Number of dead mites / mites tested) Number) × 100]. As a result, compound numbers A-1, A-2, A-3, A-4, A-5, A-6, A-9, A-10, A-11, A-12, A-14, A- 16, A-19, A-20, A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-31, A-32, A-34, A-36, A-40, A-41, A-42, A-43, A-44, A-60, A-61, A-62, A-70, A-71, A- 72, A-73, A-74, A-76, A-77, A-78, A-83, A-84, A-85, A-96, A-97, A-114, A-115, A-118, A-123, A-124, A-125, A-126, A-128, A-129, A-131, A-132, A-133, A-134, A-136, A- 137, A-138, A-139, A-140, A-141, A-142, A-149, A-164, A-165, A-166, A-167, A-171, A-172, The compounds of the invention of A-174, A-175 and A-180 showed acaricide control rates of 100%. On the other hand, Comparative Agent A had a mite killing rate of 0%. Test Example 3: Soil perfusion treatment test for Tetranychus urticae: A 1.2-leaf eggplant planted in a plastic tank with a diameter of 4 cm was placed in a receiving tray, and the water dilution solution of the emulsion prepared according to Formulation Example 1 (100 ppm) 20 ml perfusion treatment was applied to the soil surface of the roots of the plants. One day after the treatment, the eggplant seedlings were inoculated with 10 female adults of Tetranychus urticae (one concentration, repeated twice). After treatment, keep it in a constant temperature room at 25 ° C. After 3 days of treatment, the life and death and knockdown of the adult were investigated. The knockdown was considered dead and the mite killing rate (%) was calculated. [(Number of dead mites / number of mites tested) × 100] . As a result, A-2, A-3, A-4, A-5, A-6, A-10, A-12, A-20, A-25, A-26, A-27, A-28, A-60, A-61, A-71, A-72, A-74, A-77, A-78, A-85, A-115, A-164, A-165, A-166, A- 167, A-174 and A-175 showed 100% acaricidal rates. On the other hand, Comparative Agent A had a mite killing rate of 0%.

Claims (15)

A 1-phenylpiperidine derivative, an N-oxide or a salt thereof, the 1-phenylpiperidine derivative is represented by the following formula (1), [Wherein R represents a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, and a C _2-6 haloalkynyl group , C _3-6 cycloalkyl C _1-6 alkyl or C _3-6 halocycloalkyl C _1-6 alkyl, X represents C _1-6 alkyl, C _1-6 haloalkyl, C _{3- 6} cycloalkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _2-6 haloalkenyl, C _2-6 haloalkynyl, C _1-6 alkoxy, C _1-6 haloalkoxy , C _3-6 halocycloalkyl, C _1-6 alkoxymethyl, C _1-6 haloalkoxymethyl, optionally substituted benzyloxymethyl, C _1-6 alkoxycarbonyl , C _1-6 alkylcarbonyl, hydroxymethyl, formamyl, halogen atom, cyano, amine, nitro, -CH = NOR ¹ , 2,2-dicyanovinyl, represented by the following formula A, or a saturated heterocyclic ring containing oxygen or sulfur, Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group, Z may be the same or different, and represents a C _1-6 haloalkyl group, and R ¹ represents a C _1-6 alkyl group, C _1-6 haloalkyl, or benzyl, n represents an integer of 0, 1 or 2, and m represents an integer of 1 to 3]. For example, a 1-phenylpiperidine derivative, an N-oxide or a salt thereof of claim 1, wherein R represents a C _1-6 alkyl group or a C _1-6 haloalkyl group. For example, a 1-phenylpiperidine derivative, an N-oxide or a salt thereof of claim 1, wherein X represents a C _1-6 alkyl group, a C _1-6 haloalkyl group, a halogen atom, a C _1-6 alkoxy group Methyl or cyano. A 1-phenylpiperidine derivative, an N-oxide or a salt thereof according to any one of claims 1 to 3, wherein m represents 1. A method for producing a 1-phenylpiperidine derivative, which is a method for producing a 1-phenylpiperidine derivative represented by the following formula (2), [Wherein R represents a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, and a C _2-6 haloalkynyl group , C _3-6 cycloalkyl C _1-6 alkyl or C _3-6 halocycloalkyl C _1-6 alkyl, X represents C _1-6 alkyl, C _1-6 haloalkyl, C _{3- 6} cycloalkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _2-6 haloalkenyl, C _2-6 haloalkynyl, C _1-6 alkoxy, C _1-6 haloalkoxy , C _3-6 halocycloalkyl, C _1-6 alkoxymethyl, C _1-6 haloalkoxymethyl, optionally substituted benzyloxymethyl, C _1-6 alkoxycarbonyl , C _1-6 alkylcarbonyl, hydroxymethyl, formamyl, halogen atom, cyano, amine, nitro, -CH = NOR ¹ , 2,2-dicyanovinyl, represented by the following formula A, or a saturated heterocyclic ring containing oxygen or sulfur, Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group, Z may be the same or different, and represents a C _1-6 haloalkyl group, and R ¹ represents a C _1-6 alkyl group, C _1-6 haloalkyl, or benzyl, m represents an integer of 1 to 3] and includes the step of: combining the 1-phenylpiperidine derivative represented by the following formula (3) with the following formula (4) Thiols react, [Wherein X, Y, Z and m are as defined in formula (2), halo ¹ represents a halogen atom] [Wherein R is as defined in formula (2)]. A method for producing a 1-phenylpiperidine derivative, which is a method for producing a 1-phenylpiperidine derivative represented by the following formula (3), [Wherein X represents C _1-6 alkyl, C _1-6 haloalkyl, C _3-6 cycloalkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _2-6 haloalkenyl , C _2-6 haloalkynyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _3-6 halocycloalkyl, C _1-6 alkoxymethyl, C _1-6 halo Alkoxymethyl, optionally substituted benzyloxymethyl, C _1-6 alkoxycarbonyl, C _1-6 alkylcarbonyl, hydroxymethyl, formamyl, halogen atom, cyano, amine, Nitro, -CH = NOR ¹ , 2,2-dicyanovinyl, A represented by the following formula, or a saturated heterocyclic ring containing oxygen or sulfur, Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group, Z may be the same or different, and represents a C _1-6 haloalkyl group, and R ¹ represents a C _1-6 alkyl group, C _1-6 haloalkyl, or benzyl, m represents an integer of 1 to 3] and includes the following steps: a 1-phenyl derivative represented by the following formula (5) and a piperidine represented by the following formula (6) The derivative reacts, [Wherein X and Y are as defined in formula (2), and halo ¹ and halo ² each independently represent a halogen atom] [Wherein Z and m are as defined in formula (3)]. A method for producing a 1-phenylpiperidine derivative, which is a method for producing a 1-phenylpiperidine derivative represented by the following formula (2), [Wherein R represents a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, and a C _2-6 haloalkynyl group , C _3-6 cycloalkyl C _1-6 alkyl or C _3-6 halocycloalkyl C _1-6 alkyl, X represents C _1-6 alkyl, C _1-6 haloalkyl, C _{3- 6} cycloalkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _2-6 haloalkenyl, C _2-6 haloalkynyl, C _1-6 alkoxy, C _1-6 haloalkoxy , C _3-6 halocycloalkyl, C _1-6 alkoxymethyl, C _1-6 haloalkoxymethyl, optionally substituted benzyloxymethyl, C _1-6 alkoxycarbonyl , C _1-6 alkylcarbonyl, hydroxymethyl, formamyl, halogen atom, cyano, amine, nitro, -CH = NOR ¹ , 2,2-dicyanovinyl, represented by the following formula A, or a saturated heterocyclic ring containing oxygen or sulfur, Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group, Z may be the same or different, and represents a C _1-6 haloalkyl group, and R ¹ represents a C _1-6 alkyl group, C _1-6 haloalkyl, or benzyl, m represents an integer of 1 to 3] and includes the step of reacting a 1-phenylpiperidine derivative represented by formula (3) with an alkali metal sulfide to obtain the following A thiol derivative represented by formula (7), and then reacting the thiol derivative with an alkylating agent represented by the following formula (8), [Wherein X, Y, Z and m are as defined in formula (2), halo ¹ represents a halogen atom] [Wherein X, Y, Z, and m are as defined in formula (3)] [In the formula, R is as defined in formula (1), and M represents chlorine, bromine, iodine, tosylate, mesylate, or triflate]. An agricultural and horticultural agent containing the 1-phenylpiperidine derivative according to any one of claims 1 to 4, its N-oxide or a salt thereof. A mite control agent for agriculture and horticulture, which contains a 1-phenylpiperidine derivative according to any one of claims 1 to 4, an N-oxide or a salt thereof. A nematode control agent for agriculture and horticulture, comprising a 1-phenylpiperidine derivative according to any one of claims 1 to 4, an N-oxide or a salt thereof. A pest control agent for agriculture and horticulture, which contains a 1-phenylpiperidine derivative according to any one of claims 1 to 4, an N-oxide or a salt thereof. An agricultural and horticultural disease control agent containing the 1-phenylpiperidine derivative according to any one of claims 1 to 4, its N-oxide or a salt thereof. A method for controlling plant pests, comprising the steps of using the agricultural and horticultural agents as claimed in claim 8 to treat the pests and / or their living environment and / or seeds and / or plant bodies and / or plant propagation materials For processing. A method for controlling plant pests, which comprises the steps of using the agricultural and horticultural agent as claimed in claim 8 to treat a place where a useful crop is to be grown, or a place where it is grown, or a growing crop. A method for preparing a pesticide composition, which is a method for preparing a pesticide composition, and includes the steps of: adding an extender and / or a surfactant to the agricultural and horticultural agent according to claim 8.