JP2015036377A - Substituted phenylpiperazine compound and pest control agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a pest control agent for controlling harmful organisms in agricultural and horticultural fields or harmful organisms to an animal such as a pet and a domestic animal or a domestic animal.SOLUTION: There is provided a substituted phenyl-piperazine compound represented by the following formula (1) or a salt thereof. (wherein, A represents an alkyl group having 1 to 20 carbon atoms which may be substituted or the like; R represents an alkyl group having 1 to 20 carbon atoms which may be substituted or the like; X represents an alkyl having 1 to 6 carbon atoms which may be substituted with a halogen atom, a cyano group or the like; Y represents a halogen atom and an alkyl group having 1 to 6 carbon atoms which may be substituted; m represents any one of integers of 0 to 4; n represents any one of integers of 0 to 8; p represents any one of integers of 0 to 2; and q and r represent any one of integers of 0 to 1.)

Description

  The present invention relates to a novel substituted phenyl piperazine compound or a salt thereof, and a pest control agent containing the substituted phenyl piperazine compound or a salt thereof.

  To date, many pesticides have been used to control pests in agricultural and horticultural situations, and animals such as pets and livestock, and livestock. Even if such effects are obtained, pests may become resistant to these drugs, and the controlling effect may be reduced. Some of the widely used pest control agents are highly toxic not only to pests but also to human livestock and fish and shellfish, and because they are persistent, they accumulate in the environment and cause environmental pollution. There are very few pesticides that exhibit high performance in all aspects. Therefore, it shows a sufficient control effect at low doses against various pests that have acquired resistance to conventional general-purpose pest control agents, and is highly safe against useful organisms and has little adverse effect on the environment. Development of a new pest control agent is eagerly desired.

  By the way, biologically active substances related to substituted phenylpiperazine compounds have been known so far. For example, Patent Documents 1 and 2 describe a compound having a piperazine skeleton similar to the compound according to the present invention. However, Patent Documents 1 and 2 describe the control effect on pests and the present invention. There is no description of such compounds.

International Publication No. 1999/019301 International Publication No. 2005/023260

  An object of the present invention is to provide a novel substituted phenylpiperazine compound or a salt thereof having a pest control effect, and a pest control agent containing the substituted phenylpiperazine compound or a salt thereof.

  As a result of intensive studies to solve the above problems, the present inventor has found that the substituted phenylpiperazine compound represented by the following formula (1) or a salt thereof has an excellent control effect against pests. It came to complete.

  That is, the 1st aspect of the invention which concerns on this application is related with the substituted phenyl piperazine compound or its salt represented by following formula (1).

In the above formula (1), A is one or more of which can be substituted by _{G 1 C} 1 _{-C 20} alkyl group, one or more may be substituted with _{G 1 C} 2 _{-C 20} alkenyl group, one or more may be substituted with _{G 1 C} 2 _{-C 20} alkynyl group, one or more may be substituted with _{G 1 C} 3 _{-C 20} cycloalkyl group, substituted with one or more in _{G 1} which may be _C 3 _{-C 20} cycloalkenyl group, one or more may be substituted with _{G 1 C} 1 _{-C 20} haloalkyl group, one or more may be substituted with _{G 1 C} 2 _{-C 20} halo an alkenyl group or at least one optionally substituted with _{G 1 C} 2 _{-C 20} haloalkynyl group.

G ₁ is a cyano group, a cycloalkyl group, an alkoxy group, an alkylthio group, an alkylamino group, a dialkylamino group, an alkoxycarbonyl group, an aryl group optionally substituted with one or more G ₅ , or one or more be substituted with G ₅ represents an heterocycle.

In the above formula (1), R is a hydrogen atom, a cyano group, a formyl group, a halocarbonyl group, a thioformyl group, a C ₁ -C ₂₀ alkyl group optionally substituted with one or more G ₂ , one or more may be substituted with G _{2 C 2} ~C ₂₀ alkenyl group, one or more optionally substituted with _{G 2 C 2 ~C 20} alkynyl group, one or more _{G 3} may be substituted by _{C 3} -C ₂₀ cycloalkyl group, one or more optionally substituted with _{G 3 C 3 ~C 20} cycloalkyl group, one or more optionally substituted with _{G 2 C} 1 _{-C 20} alkylcarbonyl group, 1 one or more substituted with _{G 2 C} 1 may be _{-C 20} alkyl thio group, one or more optionally substituted with _{G 2 C 2 ~C 20} alkenylcarbonyl group, substituted by one or more _{G 2} which may be _C 2 _{~C 20} alkenyl Thiocarbonyl group, one or more optionally substituted with _{G 2 C 2 ~C 20} alkynyl group, one or more optionally substituted with _{G 3 C 3 ~C 20} cycloalkyl group, one or more optionally substituted _C 3 _{-C 20} cycloalkylthio group in _{G 3,} the one or more optionally substituted with _{G 3 C 3 ~C 20} cycloalkyl group, substituted with one or more _{G 2} which may be _C 1 _{-C 20} alkoxycarbonyl group, one or more optionally substituted with _{G 2 C} 1 _{-C 20} alkoxy thiocarbonyl group, one or more substituted with _{G 2} good _C 1 be -C ₂₀ alkylaminocarbonyl group, _C 1 may be substituted by one or more _{G 2 -C 20} alkylaminothiocarbonyl group, one or more _di-C 2 may be substituted with _{G 2} of -C ₂ Alkylaminocarbonyl group, one or more _di-C 2 may be substituted with _{G 2} of _{-C 20} alkylamino thiocarbonyl group, one or more optionally substituted with _{G 3 C 3 ~C 20} cycloalkyl aminocarbonyl group, a hydroxyl group, one or more optionally substituted with _{G 2 C} 1 _{-C 20} alkoxy group, one or more optionally substituted with _{G 2 C} 1 _{-C 20} alkylamino group, one or more G ₂ di _C 2 may be substituted with _{-C 20} alkylamino group, halosulfonyl group, one or more optionally substituted with _{G 2 C} 1 _{-C 20} alkylsulfonyl group, at least one _{G 2} optionally substituted _C 2 _{-C 20} alkenyl-sulfonyl group, one or more optionally substituted with _{G 3 C 3 ~C 20} cycloalkyl alkylsulfonyl group which may be substituted by one or more _{G 2} C -C ₂₀ alkyl aminosulfonyl group, one or more _{G 2} substituted by _di-C 2 may be _{-C 20} alkyl aminosulfonyl group, one or more good di _C 4 be substituted with _{G 2 -C 20} alkenyl aminosulfonyl group, one or more di-C ₄ may be substituted by G ₂ -C ₂₀ alkynyl aminosulfonyl group, one or more di-C ₆ optionally substituted by G ₃ of -C ₂₀ cycloalkyl aminosulfonyl group , one or more tri C ₃ may be substituted with G ₂ of -C ₂₀ alkylsilyl group, one or more optionally substituted benzyl group in G _3, which may be substituted with one or more G ₃ arylcarbonyl group, one or more G ₃ which may be substituted with a heterocyclic carbonyl group, one or more substituted with G ₃ which may be arylthiocarbonyl group, may be substituted by one or more G ₃ Heterocyclic thiocarbonyl group, one or more G ₃ which may be substituted with arylcarbonyl group, one or more G ₃ which may be substituted with an aryloxycarbonyl group, substituted with one or more G ₃ also heterocyclic oxycarbonyl group, one or more substituted with G ₃ may be aryloxythiocarbonyl group, one or more may be substituted by G ₃ heterocyclyloxy thiocarbonyl group, one or more G _An arylaminocarbonyl group optionally substituted with ₃ , a heterocyclic aminocarbonyl group optionally substituted with one or more G ₃ , an arylaminothiocarbonyl group optionally substituted with one or more G ₃ , one more G ₃ substituted by an optionally heterocyclic amino thiocarbonyl group, one or more substituted with G ₃ may be an arylsulfonyl group, optionally substituted by one or more G ₃ There heterocyclic sulfonyl group, one or more G ₃ which may be substituted with aryl aminosulfonyl group, one or more G ₃ which may be substituted with a heterocyclic aminosulfonyl group is substituted with one or more G ₃ 1 represents an aryl group that may be substituted, or a heterocycle that may be substituted with one or more G ₃ .

G ₂ is a halogen atom, cyano group, cycloalkyl group, alkoxy group, alkylthio group, alkylamino group, dialkylamino group, alkylsulfinyl group, alkylcarbonyl group, cycloalkylcarbonyl group, alkoxycarbonyl group, alkoxyimino group, alkenyloxy imino group, alkynyloxy imino group, halo alkoxyiminoalkyl group, one or more G ₅ which may be substituted with an aryl group, one or more heterocyclic ring which may be substituted with G _5, one or more G _An arylcarbonyl group that may be substituted with ₅ , a heterocyclic carbonyl group that may be substituted with one or more G ₅ , or an aryloxy group that may be substituted with one or more G ₅ are shown.

G ₃ is a halogen atom, cyano group, nitro group, alkyl group, alkenyl group, alkynyl group, haloalkyl group, cycloalkyl group, alkoxy group, haloalkoxy group, alkylthio group, haloalkylthio group, alkylsulfinyl group, haloalkylsulfinyl group. Group, alkylsulfonyl group, haloalkylsulfonyl group, alkylamino group, dialkylamino group, alkenylamino group, alkynylamino group, alkylcarbonyl group, alkoxycarbonyl group, alkylaminocarbonyl group, haloalkylaminocarbonyl group, alkylcarbonylaminoalkyl group, one or more G ₅ which may be substituted with an aryl group, one or more G ₅ which may be substituted with an aryloxy group, one or more G ₅ with an optionally substituted benzyl group, one or more in G ₅ Conversion which may be a benzoyl group, one or more G ₅ heterocyclic ring which may be substituted by or one or more substituted with G ₅ may be a heterocyclic oxy group,.

G ₅ is a halogen atom, cyano group, nitro group, alkyl group, alkenyl group, alkynyl group, haloalkyl group, cycloalkyl group, alkoxy group, haloalkoxy group, alkylthio group, haloalkylthio group, alkylamino group, dialkylamino Group, a haloalkylamino group.

In the above formula (1), X is a halogen atom, a cyano group, a nitro group, may be substituted with a halogen atom C ₁ -C ₆ alkyl group, optionally C ₁ -C ₆ alkoxy group optionally substituted by a halogen atom Or a C ₁ -C ₆ alkylthio group which may be substituted with a halogen atom.

In the above formula (1), Y is a halogen atom, an oxygen atom, a sulfur atom, one or more may be substituted by _{G 4 C} 1 -C ₆ alkyl group, optionally substituted by one or more _{G 4} good _C 1 -C ₆ haloalkyl group, one or more may be substituted by _{G 4 C} 3 _{~C 6} cycloalkyl group, or one or more may be substituted by _{G 4 C} 1 -C ₆ alkoxy group, Indicates.

  However, two Y on the same carbon can also represent (= O) or (= S), and can also form (C = O) or (C = S). Two Ys may be bonded to each other to represent a carbocyclic or heterocyclic ring. Y may be the same or different.

G ₄ represents a cyano group, an alkoxy group, an alkylthio group, an alkylamino group, a dialkylamino group, or an alkoxycarbonyl group.

  In the above formula (1), m represents any integer of 0 to 4, n represents any integer of 0 to 8, p represents any integer of 0 to 2, q And r represents an integer of 0 to 1.

  The 2nd aspect of the invention which concerns on this application is related with the pest control agent containing at least 1 type of the substituted phenyl piperazine compound or its salt represented by the said Formula (1).

  ADVANTAGE OF THE INVENTION According to this invention, the pest control agent containing the novel substituted phenyl piperazine compound or its salt which has the control effect with respect to a pest, and a substituted phenyl piperazine compound or its salt can be provided.

Hereinafter, the present invention will be described in detail.
The substituted phenyl piperazine compound according to the present invention has a piperazine skeleton represented by the following formula (1) as a basic skeleton.

In the above formula (1), the C _{1 to} C ₂₀ alkyl group represented by A includes methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec- Examples include a butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, and an n-decyl group. Here, _C 1 _{-C 20} alkyl group represented by A may be substituted by one or more _{G 1.}

G ₁ is a cyano group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclopentyl group, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, tert-butoxy group, Methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, tert-butylthio group, methylamino group, ethylamino group, n-propylamino group, i-propylamino group, n-butylamino Group, tert-butylamino group, dimethylamino group, methylethylamino group, diethylamino group, di-n-propylamino group, di-i-propylamino group, di-n-butylamino group, di-i-butylamino Group, di-sec-butylamino group, di-tert-butylamino group, di-n-pe Nthylamino group, di-n-hexylamino group, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, tert-butoxycarbonyl group, substituted with one or more G ₅ is also a phenyl group, one or more G ₅ which may be substituted with a naphthyl group, one or more G _{5-substituted} 2-pyridyl which may be groups, it is substituted by one or more G ₅ good 3-pyridyl group, substituted one or more G ₅ in which may be substituted also 4-pyridyl group, one or more G ₅ in which may be substituted also a 2-thienyl group, or with one or more G _5, 3-thienyl group etc. which may be mentioned are mentioned.

G ₅ is fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, nitro group, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec -Butyl group, tert-butyl group, n-pentyl group, n-hexyl group, vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl 2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2- Butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butenyl Tinyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl- 2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromo Methyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group , Nonafluorobutyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclopentyl group, metho Si group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, tert-butoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2- Tetrafluoroethoxy group, 3,3,3-trifluoropropoxy group, methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, tert-butylthio group, trifluoromethylthio group, 2,2 , 2-trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, 3,3,3-trifluoropropylthio group, methylamino group, ethylamino group, n-propylamino group, i -Propylamino group, n-butylamino group, tert-butylamino group, dimethylamino group, methylethylamino group, diethylamino Group, di-n-propylamino group, di-i-propylamino group, di-n-butylamino group, di-i-butylamino group, di-sec-butylamino group, di-tert-butylamino group, Di-n-pentylamino group, di-n-hexylamino group, trifluoromethylamino group, 2,2,2-trifluoroethylamino group, 1,1,2,2-tetrafluoroethylamino group, 3, Examples include 3,3-trifluoropropylamino group.

In the above formula (1), the C _{2 to} C ₂₀ alkenyl group represented by A includes a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl Examples include 2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, and 5-hexenyl group. In the formula (1), the C _{2 to} C ₂₀ alkenyl group represented by A may be substituted with one or more G ₁ .

In the above formula (1), examples of the C _{2 to} C ₂₀ alkynyl group represented by A include ethynyl group, 1-propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1- Methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3 -Pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group and the like can be mentioned. In the formula (1), the C _{2 to} C ₂₀ alkynyl group represented by A may be substituted with one or more G ₁ .

In the above formula (1), examples of the C _{3 to} C ₂₀ cycloalkyl group represented by A include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cyclopentyl group. In the formula (1), the C _{3 to} C ₂₀ cycloalkyl group represented by A may be substituted with one or more G ₁ .

In the above formula (1), the C _{3 to} C ₂₀ cycloalkenyl group represented by A includes a 1-cyclopropenyl group, a 2-cyclopropenyl group, a 1-cyclobutenyl group, a 2-cyclobutenyl group, and a 1-cyclopentenyl group. 2-cyclopentenyl group, 3-cyclopentenyl group, 1-cyclohexenyl group, 2-cyclohexenyl group, 3-cyclohexenyl group and the like. In the formula (1), the C _{3 to} C ₂₀ cycloalkenyl group represented by A may be substituted with one or more G ₁ .

In the above formula (1), the C _{1 to} C ₂₀ haloalkyl group represented by A includes a fluoromethyl group, a chloromethyl group, a bromomethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a trifluoromethyl group, Trichloromethyl group, tribromomethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 3,3,3-tri A fluoropropyl group, a heptafluoropropyl group, a nonafluorobutyl group, a heptafluoroisopropyl group and the like can be mentioned. In the formula (1), the C _{1 to} C ₂₀ haloalkyl group represented by A may be substituted with one or more G ₁ .

In the above formula (1), the C _{2 to} C ₂₀ haloalkenyl group represented by A includes a bromovinyl group, a chlorovinyl group, a 3,3-dichloro-2-propenyl group, and a 4,4-difluoro-3-butenyl. Group, 3,4,4-trifluoro-3-butenyl group and the like. In the formula (1), the C _{2 to} C ₂₀ haloalkenyl group represented by A may be substituted with one or more G ₁ .

In the above formula (1), examples of the C _{2 to} C ₂₀ haloalkynyl group represented by A include a bromopropynyl group, an iodopropynyl group, a fluoropropynyl group, a chloropropynyl group, and a chlorobutynyl group. In the formula (1), the C _{2 to} C ₂₀ haloalkynyl group represented by A may be substituted with one or more G ₁ .

  In the above formula (1), examples of the halocarbonyl group represented by R include a fluorocarbonyl group and a chlorocarbonyl group.

In the above formula (1), examples of the C _{1 to} C ₂₀ alkyl group represented by R include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec- Butyl group, tert-butyl group, n-pentyl group, neo-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-decyl group, n-dodecyl group, n-hexadecyl group, n- Examples include an eicosyl group. In the above formula (1), the C _{1 to} C ₂₀ alkyl group represented by R may be substituted with one or more G ₂ .

G ₂ represents fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclopentyl group, methoxy group, ethoxy group, n-propoxy group, i-propoxy group. Group, n-butoxy group, tert-butoxy group, methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, tert-butylthio group, methylamino group, ethylamino group, n-propylamino group Group, i-propylamino group, n-butylamino group, tert-butylamino group, dimethylamino group, methylethylamino group, diethylamino group, di-n-propylamino group, di-i-propylamino group, di- n-butylamino group, di-i-butylamino group, di-sec-butylamino Group, di-tert-butylamino group, di-n-pentylamino group, di-n-hexylamino group, methylsulfinyl group, ethylsulfinyl group, n-propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group Group, tert-butylsulfinyl group, acetyl group, propionyl group, butyryl group, i-butyryl group, valeryl group, pivaloyl group, cyclopropylcarbonyl group, 1-methylcyclopropylcarbonyl group, 2-methylcyclopropylcarbonyl group, 2 , 2-dimethylcyclopropylcarbonyl group, cyclobutylcarbonyl group, cyclopentylcarbonyl group, cyclohexylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxy Carbonyl group, tert- butoxycarbonyl group, methoxyimino group, ethoxyimino group, tert- Butokishiimino group, allyloxy imino group, propargyloxy imino group, trifluoroethoxy imino group, optionally substituted by one or more G ₅ a phenyl group, one or more G ₅ which may be substituted with a naphthyl group, one or more G _{5-substituted} 2-pyridyl which may be group may be substituted by one or more G ₅ 3- pyridyl, one or more G ₅ in which may be substituted also 4-pyridyl group, one or more G ₅ in which may be substituted also 2-thienyl group may be substituted by one or more G ₅ 3 - a thienyl group, one or more G ₅ in which may be substituted also 2-quinolyl group, one or more substituted with may be 3-quinolyl group G _5, which may be substituted with one or more G ₅ 4-quinolyl , One or more G ₅ in which may be substituted also 5-quinolyl group, one or more G ₅ in which may be substituted also 6-quinolyl group, one or more may be substituted with G ₅ 7- quinolyl group, one or more G ₅ in which may be substituted also 8-quinolyl group, one or more G ₅ in which may be substituted also a 2-thiazolyl group, may be substituted with one or more G ₅ 4- thiazolyl group, one or more G ₅ in which may be substituted also 5-thiazolyl group, one or more G ₅ in which may be substituted also 2-indolyl group, may be substituted with one or more G ₅ 3 - indolyl group, one or more G ₅ in which may be substituted also 4-indolyl group, one or more may be substituted with G ₅ 5-indolyl group, it may be substituted with one or more G ₅ 6-indolyl group, one or more may be substituted with G ₅ 4-benzothiadiazolyl group, 1 More G ₅ in which may be substituted also 5-benzothiadiazolyl group, one or more substituted with may be 6-benzothiadiazolyl group G _5, which may be substituted with one or more G ₅ 2-tetrahydrofuranyl group, one or more G ₅ which may be substituted with a benzoyl group, one or more G ₅ which may be substituted with picolinoyl group, one or more G ₅ which may be substituted with nicotinoyl group , optionally substituted isonicotinoyl group or the like one or more which may be phenoxy group substituted with G _5, and the like with one or more G _5.

In the above formula (1), examples of the C _{2 to} C ₂₀ alkenyl group represented by R include a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl Examples include 2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, and 5-hexenyl group. In the formula (1), the C _{2 to} C ₂₀ alkenyl group represented by R may be substituted with one or more G ₂ .

In the above formula (1), examples of the C _{2 to} C ₂₀ alkynyl group represented by R include ethynyl group, 1-propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1- Methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3 -Pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group and the like can be mentioned. In the formula (1), the C _{2 to} C ₂₀ alkynyl group represented by R may be substituted with one or more G ₂ .

In the above formula (1), the C ₃ -C ₂₀ cycloalkyl group represented by R includes a cyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, a 2,2-dimethylcyclopropyl group, A cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, etc. are mentioned. In the formula (1), the C _{3 to} C ₂₀ cycloalkyl group represented by R may be substituted with one or more G ₃ .

G ₃ is fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, nitro group, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec -Butyl group, tert-butyl group, n-pentyl group, n-hexyl group, vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl 2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2- Butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butenyl Tinyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl- 2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromo Methyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group , Nonafluorobutyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, metho Si group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, tert-butoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2- Tetrafluoroethoxy group, 3,3,3-trifluoropropoxy group, methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, tert-butylthio group, trifluoromethylthio group, 2,2 , 2-trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, 3,3,3-trifluoropropylthio group, methylsulfinyl group, ethylsulfinyl group, n-propylsulfinyl group, i -Propylsulfinyl group, n-butylsulfinyl group, tert-butylsulfinyl group, trifluoromethyl Sulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 1,1,2,2-tetrafluoroethylsulfinyl group, 3,3,3-trifluoropropylsulfinyl group, methylsulfonyl group, ethylsulfonyl group, n -Propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, tert-butylsulfonyl group, trifluoromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 1,1,2,2-tetra Fluoroethylsulfonyl group, 3,3,3-trifluoropropylsulfonyl group, methylamino group, ethylamino group, n-propylamino group, i-propylamino group, n-butylamino group, tert-butylamino group, dimethyl Amino group, methylethylamino group, diethylamino group, di-n -Propylamino group, di-i-propylamino group, di-n-butylamino group, di-i-butylamino group, di-sec-butylamino group, di-tert-butylamino group, di-n-pentyl Amino group, di-n-hexylamino group, vinylamino group, 1-propenylamino group, 2-propenylamino group, 1-butenylamino group, 2-butenylamino group, 3-butenylamino group, 1-propynylamino group, propargylamino Group, 1-butynylamino group, 2-butynylamino group, 3-butynylamino group, acetyl group, propionyl group, butyryl group, i-butyryl group, valeryl group, pivaloyl group, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group , Isopropoxycarbonyl group, n-butoxycarbonyl group, tert-butyl Xoxycarbonyl group, methylaminocarbonyl group, ethylaminocarbonyl group, i-propylaminocarbonyl group, butylaminocarbonyl group, i-butylaminocarbonyl group, n-pentylaminocarbonyl group, i-pentylaminocarbonyl group, n-hexyl Aminocarbonyl group, i-hexylaminocarbonyl group, trifluoromethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, 3,3,3-trifluoropropylaminocarbonyl group, acetylaminomethyl group, 1 one or more optionally substituted phenyl group G _5, one or more G ₅ with an optionally substituted naphthyl group, one or more G ₅ with an optionally substituted phenoxy group, one or more G ₅ A benzyl group that may be substituted with one or more G ₅ Nzoiru group, one or more G _{5-substituted} 2-pyridyl which may be based on, one or more may be substituted with G ₅ 3- pyridyl may be substituted with one or more G ₅ 4 - a pyridyl group, one or more G ₅ in which may be substituted also 2-thienyl group, one or more substituted with may be 3-thienyl group G _5, which may be substituted with one or more G ₅ 2-oxazolyl group, one or more G ₅ in which may be substituted also 4-oxazolyl group, one or more substituted with may be 5-oxazolyl group G _5, which may be substituted by one or more G ₅ good 2-tetrahydrofuranyl group, one or more substituted with G ₅ which may be 3-tetrahydrofuranyl group, one or more may be substituted with G ₅ 2-tetrahydropyranyl group, one or more G ₅ A 3-tetrahydropyranyl group optionally substituted with one or more ₅ which may be substituted 4-tetrahydropyranyl group, one or more substituted with G ₅ which may be 4-piperidinyl group, one or more G ₅ may be substituted 2- tetrahydrothiopyranyl group one or more substituted with G ₅ which may be 3-tetrahydrothiopyranyl group, one or more may be substituted with G ₅ 4-tetrahydrothiopyranyl group, substituted by one or more G ₅ and it may be 2-pyridyloxy group, such as one or more substituted with G ₅ which may be 3-pyridyloxy group or at least one G ₅ in which may be substituted 4-pyridyloxy group, and the like.

In the above formula (1), the C _{3 to} C ₂₀ cycloalkenyl group represented by R includes a 1-cyclopropenyl group, a 2-cyclopropenyl group, a 1-cyclobutenyl group, a 2-cyclobutenyl group, and a 1-cyclopentenyl group. 2-cyclopentenyl group, 3-cyclopentenyl group, 1-cyclohexenyl group, 2-cyclohexenyl group, 3-cyclohexenyl group and the like. In the formula (1), the C _{3 to} C ₂₀ cycloalkenyl group represented by R may be substituted with one or more G ₃ .

The formula (1), as the _C 1 _{-C 20} alkylcarbonyl group represented by R, an acetyl group, a propionyl group, a butyryl group, i- butyryl group, valeryl group, pivaloyl group and the like. In the formula (1), the C _{1 to} C ₂₀ alkylcarbonyl group represented by R may be substituted with one or more G ₂ . The carbon number of the alkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atom of the carbonyl group.

The formula (1), as the _C 1 _{-C 20} alkyl thio group represented by R, thioacetyl group, thiopropionyl group, Chiobuchiriru group, thio -i- butyryl group, Chiobareriru group, etc. Chiopibaroiru group. In the formula (1), the C _{1 to} C ₂₀ alkylthiocarbonyl group represented by R may be substituted with one or more G ₂ . The carbon number of the alkylthiocarbonyl group represented by C is the number of carbon atoms excluding the carbon atom of the thiocarbonyl group.

In the above formula (1), examples of the C _{2 to} C ₂₀ alkenylcarbonyl group represented by R include an acryloyl group and a methacryloyl group. In the formula (1), the C _{2 to} C ₂₀ alkenylcarbonyl group represented by R may be substituted with one or more G ₂ . The carbon number of the alkenylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atom of the carbonyl group.

In the above formula (1), examples of the C _{2 to} C ₂₀ alkenylthiocarbonyl group represented by R include a thioacryloyl group and a thiomethacryloyl group. In the formula (1), the C _{2 to} C ₂₀ alkenylthiocarbonyl group represented by R may be substituted with one or more G ₂ . The carbon number of the alkenylthiocarbonyl group represented by C is the number of carbon atoms excluding the carbon atom of the thiocarbonyl group.

In the above formula (1), examples of the C _{2 to} C ₂₀ alkynylcarbonyl group represented by R include a propioyl group and a methylpropioyl group. In the formula (1), the C _{2 to} C ₂₀ alkynylcarbonyl group represented by R may be substituted with one or more G ₂ . The carbon number of the alkynylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atom of the carbonyl group.

In the above formula (1), the C _{3 to} C ₂₀ cycloalkylcarbonyl group represented by R includes a cyclopropylcarbonyl group, a 1-methylcyclopropylcarbonyl group, a 2-methylcyclopropylcarbonyl group, 2,2-dimethyl. A cyclopropylcarbonyl group, a cyclobutylcarbonyl group, a cyclopentylcarbonyl group, a cyclohexylcarbonyl group, etc. are mentioned. In the formula (1), the C _{3 to} C ₂₀ cycloalkylcarbonyl group represented by R may be substituted with one or more G ₃ . The carbon number of the cycloalkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atom of the carbonyl group.

In the above formula (1), the C _{3 to} C ₂₀ cycloalkylthiocarbonyl group represented by R includes a cyclopropylthiocarbonyl group, a 1-methylcyclopropylthiocarbonyl group, a 2-methylcyclopropylthiocarbonyl group, 2, Examples include 2-dimethylcyclopropylthiocarbonyl group, cyclopentylthiocarbonyl group, cyclohexylthiocarbonyl group and the like. In the formula (1), the C _{3 to} C ₂₀ cycloalkylthiocarbonyl group represented by R may be substituted with one or more G ₃ . The carbon number of the cycloalkylthiocarbonyl group represented by C is the number of carbon atoms excluding the carbon atom of the thiocarbonyl group.

In the above formula (1), the C _{3 to} C ₂₀ cycloalkenylcarbonyl group represented by R includes a 1-cyclopropenylcarbonyl group, a 2-cyclopropenylcarbonyl group, a 1-cyclobutenylcarbonyl group, and a 2-cyclobutyl group. Examples include a tenenylcarbonyl group, a 1-cyclopentenylcarbonyl group, a 2-cyclopentenylcarbonyl group, a 3-cyclopentenylcarbonyl group, a 1-cyclohexenylcarbonyl group, a 2-cyclohexenylcarbonyl group, and a 3-cyclohexenylcarbonyl group. In the formula (1), the C _{3 to} C ₂₀ cycloalkenylcarbonyl group represented by R may be substituted with one or more G ₃ . The carbon number of the cycloalkenylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atom of the carbonyl group.

In the formula (1), as the _C 1 _{-C 20} alkoxycarbonyl group represented by R, a methoxycarbonyl group, an ethoxycarbonyl group, n- propoxycarbonyl group, i- propoxycarbonyl group, n- butoxycarbonyl group, tert -Butoxycarbonyl group etc. are mentioned. In the formula (1), the C _{1 to} C ₂₀ alkoxycarbonyl group represented by R may be substituted with one or more G ₂ . The number of carbon atoms of the alkoxycarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1), examples of the C _{1 to} C ₂₀ alkoxythiocarbonyl group represented by R include a methoxythiocarbonyl group and an ethoxythiocarbonyl group. In the formula (1), the C _{1 to} C ₂₀ alkoxythiocarbonyl group represented by R may be substituted with one or more G ₂ . The number of carbon atoms of the alkoxythiocarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the thiocarbonyl group.

In the above formula (1), as the _C 1 _{-C 20} alkylaminocarbonyl group represented by R, methylaminocarbonyl group, ethylaminocarbonyl group, i- propylamino group, n- butylamino group, i- A butylaminocarbonyl group, n-pentylaminocarbonyl group, i-pentylaminocarbonyl group, n-hexylaminocarbonyl group, i-hexylaminocarbonyl group and the like can be mentioned. In the formula (1), the C _{1 to} C ₂₀ alkylaminocarbonyl group represented by R may be substituted with one or more G ₂ . The carbon number of the alkylaminocarbonyl group represented by C is the number of carbon atoms excluding the carbon atom of the carbonyl group.

In the above formula (1), the C _{1 to} C ₂₀ alkylaminothiocarbonyl group represented by R includes a methylaminothiocarbonyl group, an ethylaminothiocarbonyl group, an n-propylaminothiocarbonyl group, an i-propylaminothio group. Carbonyl group, n-butylaminothiocarbonyl group, i-butylaminothiocarbonyl group, n-pentylaminothiocarbonyl group, i-pentylaminothiocarbonyl group, n-hexylaminothiocarbonyl group, i-hexylaminothiocarbonyl group Etc. In the formula (1), the C _{1 to} C ₂₀ alkylaminothiocarbonyl group represented by R may be substituted with one or more G ₂ . The carbon number of the alkylaminothiocarbonyl group represented by C is the number of carbon atoms excluding the carbon atom of the thiocarbonyl group.

In the above formula (1), the di-C ₂ -C ₂₀ alkylaminocarbonyl group represented by R includes a dimethylaminocarbonyl group, a methylethylaminocarbonyl group, a diethylaminocarbonyl group, a di-n-propylaminocarbonyl group, a di- -I-propylaminocarbonyl group, di-n-butylaminocarbonyl group, di-i-butylaminocarbonyl group, di-sec-butylaminocarbonyl group, di-tert-butylaminocarbonyl group, di-n-pentylamino A carbonyl group, a di-n-hexylaminocarbonyl group, a methylcyclohexylaminocarbonyl group and the like can be mentioned. In the above formula (1), the di-C ₂ -C ₂₀ alkylaminocarbonyl group represented by R may be substituted with one or more G ₂ . The carbon number of the dialkylaminocarbonyl group represented by C is the number of carbon atoms excluding the carbon atom of the carbonyl group.

In the above formula (1), the C _{3 to} C ₂₀ cycloalkylaminocarbonyl group represented by R includes a cyclopropylaminocarbonyl group, a 1-methylcyclopropylaminocarbonyl group, a 2-methylcyclopropylaminocarbonyl group, 2 , 2-dimethylcyclopropylaminocarbonyl group, cyclobutylaminocarbonyl group, cyclopentylaminocarbonyl group, cyclohexylaminocarbonyl group and the like. In the formula (1), the C _{3 to} C ₂₀ cycloalkylaminocarbonyl group represented by R may be substituted with one or more G ₃ . The carbon number of the cycloalkylaminocarbonyl group represented by C is the number of carbon atoms excluding the carbon atom of the carbonyl group.

In the above formula (1), as the _C 1 _{-C 20} alkoxy group represented by R, include a methoxy group, an ethoxy group, n- propoxy group, i- propoxy, n- butoxy group, etc. tert- butoxy It is done. In the formula (1), the C _{1 to} C ₂₀ alkoxy group represented by R may be substituted with one or more G ₂ .

In the above formula (1), examples of the C _{1 to} C ₂₀ alkylamino group represented by R include a methylamino group and an ethylamino group. In the formula (1), the C _{1 to} C ₂₀ alkylamino group represented by R may be substituted with one or more G ₂ .

In the above formula (1), examples of the di-C ₂ -C ₂₀ alkylamino group represented by R include a dimethylamino group and a diethylamino group. In the above formula (1), the di-C ₂ -C ₂₀ alkylamino group represented by R may be substituted with one or more G ₂ .

  In the above formula (1), examples of the halosulfonyl group represented by R include a fluorosulfonyl group and a chlorosulfonyl group.

In the formula (1), as the _C 1 _{-C 20} alkylsulfonyl group represented by R, methylsulfonyl group, ethylsulfonyl group, n- propylsulfonyl group, i- propylsulfonyl group, n- butylsulfonyl group, i -Butylsulfonyl group, n-pentylsulfonyl group, i-pentylsulfonyl group, n-hexylsulfonyl group, i-hexylsulfonyl group and the like can be mentioned. In the formula (1), the C _{1 to} C ₂₀ alkylsulfonyl group represented by R may be substituted with one or more G ₂ .

The formula (1), as the C ₂ -C ₂₀ alkenyl sulfonyl group represented by R, vinylsulfonyl group, an allyl sulfonyl group. In the formula (1), the C _{2 to} C ₂₀ alkenylsulfonyl group represented by R may be substituted with one or more G ₂ .

In the above formula (1), examples of the C _{3 to} C ₂₀ cycloalkylsulfonyl group represented by R include a cyclopropylsulfonyl group, a cyclobutylsulfonyl group, a cyclopentylsulfonyl group, a cyclohexylsulfonyl group, and the like. In the formula (1), the C _{3 to} C ₂₀ cycloalkylsulfonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), as the C ₁ -C ₂₀ alkyl aminosulfonyl group represented by R, methylaminosulfonyl group, ethylaminosulfonyl group, n- propyl aminosulfonyl group, i- propyl aminosulfonyl group, n- Examples include a butylaminosulfonyl group, i-butylaminosulfonyl group, n-pentylaminosulfonyl group, i-pentylaminosulfonyl group, n-hexylaminosulfonyl group, i-hexylaminosulfonyl group and the like. In the formula (1), the C _{1 to} C ₂₀ alkylaminosulfonyl group represented by R may be substituted with one or more G ₂ .

In the above formula (1), examples of the di-C ₂ -C ₂₀ alkylaminosulfonyl group represented by R include a dimethylaminosulfonyl group, a methylethylaminosulfonyl group, a diethylaminosulfonyl group, a di-n-propylaminosulfonyl group, a di- -I-propylaminosulfonyl group, di-n-butylaminosulfonyl group, di-i-butylaminosulfonyl group, di-sec-butylaminosulfonyl group, di-tert-butylaminosulfonyl group, di-n-pentylamino A sulfonyl group, a di-n-hexylaminosulfonyl group, etc. are mentioned. In the above formula (1), the di-C ₂ -C ₂₀ alkylaminosulfonyl group represented by R may be substituted with one or more G ₂ .

In the above formula (1), examples of the di-C _{4 to} C ₂₀ alkenylaminosulfonyl group represented by R include a diallylaminosulfonyl group and a di1-hexenylaminosulfonyl group. In the above formula (1), the di-C ₄ -C ₂₀ alkenylaminosulfonyl group represented by R may be substituted with one or more G ₂ .

In the above formula (1), examples of the di-C _{4 to} C ₂₀ alkynylaminosulfonyl group represented by R include a dipropargylaminosulfonyl group and a di1-butynylaminosulfonyl group. In the above formula (1), the di-C _{4 to} C ₂₀ alkynylaminosulfonyl group represented by R may be substituted with one or more G ₂ .

In the above formula (1), examples of the di-C ₆ -C ₂₀ cycloalkylaminosulfonyl group represented by R include a dicyclopropylaminosulfonyl group and a dicyclohexylaminosulfonyl group. In the above formula (1), the di-C ₆ -C ₂₀ cycloalkylaminosulfonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the tri C _{3 to} C ₂₀ alkylsilyl group represented by R include a trimethylsilyl group, a triethylsilyl group, a dimethyl-tert-butylsilyl group, and the like. In the above formula (1), the tri C _{3 to} C ₂₀ alkylsilyl group represented by R may be substituted with one or more G ₂ .

In the above formula (1), the benzyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the arylcarbonyl group represented by R include a benzoyl group and a naphthoyl group. In the above formula (1), the arylcarbonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the heterocyclic carbonyl group represented by R include a picolinoyl group, a nicotinoyl group, an isonicotinoyl group, a 2-thiophenecarbonyl group, and a 3-thiophenecarbonyl group. In the above formula (1), the heterocyclic carbonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the arylthiocarbonyl group represented by R include a thiobenzoyl group and a thionaphthoyl group. In the above formula (1), the arylthiocarbonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the heterocyclic thiocarbonyl group represented by R include a thiopicolinoyl group, a thionicotinoyl group, a thioisonicotinoyl group, a 2-thiophenthiothiocarbonyl group, and a 3-thiophenthiothiocarbonyl group. In the formula (1), the heterocyclic thiocarbonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the arylcarbonylcarbonyl group represented by R include a benzoylcarbonyl group and a naphthoylcarbonyl group. In the above formula (1), the arylcarbonylcarbonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the aryloxycarbonyl group represented by R include a phenoxycarbonyl group and a naphthyloxycarbonyl group. In the above formula (1), the aryloxycarbonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the heterocyclic oxycarbonyl group represented by R include 2-pyridyloxycarbonyl group, 3-pyridyloxycarbonyl group, 4-pyridyloxycarbonyl group, 2-thienyloxycarbonyl group, 3- Examples include thienyloxycarbonyl group. In the above formula (1), the heterocyclic oxycarbonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the aryloxythiocarbonyl group represented by R include a phenoxythiocarbonyl group and a naphthyloxythiocarbonyl group. In the above formula (1), the aryloxythiocarbonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the heterocyclic oxythiocarbonyl group represented by R include 2-pyridyloxythiocarbonyl group, 3-pyridyloxythiocarbonyl group, 4-pyridyloxythiocarbonyl group, 2-thienyloxythio group. Examples thereof include a carbonyl group and a 3-thienyloxythiocarbonyl group. In the above formula (1), the heterocyclic oxythiocarbonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the arylaminocarbonyl group represented by R include phenylaminocarbonyl and naphthylaminocarbonyl groups. In the above formula (1), the arylaminocarbonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), the heterocyclic aminocarbonyl group represented by R includes 2-pyridylaminocarbonyl group, 3-pyridylaminocarbonyl group, 4-pyridylaminocarbonyl group, 2-thienylaminocarbonyl group, 3-thienylaminocarbonyl group. Groups and the like. In the above formula (1), the heterocyclic aminocarbonyl group represented by R may be substituted with one or more G ₃ groups.

In the above formula (1), examples of the arylaminothiocarbonyl group represented by R include phenylaminothiocarbonyl group and naphthylaminothiocarbonyl group. In the above formula (1), the arylaminothiocarbonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), as the heterocyclic aminothiocarbonyl group represented by R, 2-pyridylaminothiocarbonyl group, 3-pyridylaminothiocarbonyl group, 4-pyridylaminothiocarbonyl group, 2-thienylaminothiocarbonyl group, 3-thienylaminothiocarbonyl group etc. are mentioned. In the above formula (1), the heterocyclic aminothiocarbonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the arylsulfonyl group represented by R include a phenylsulfonyl group and a naphthylsulfonyl group. In the above formula (1), the arylsulfonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the heterocyclic sulfonyl group represented by R include 2-pyridylsulfonyl group, 3-pyridylsulfonyl group, 4-pyridylsulfonyl group, 2-thienylsulfonyl group, 3-thienylsulfonyl group and the like. Can be mentioned. In the above formula (1), the heterocyclic sulfonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the arylaminosulfonyl group represented by R include a phenylaminosulfonyl group and a naphthylaminosulfonyl group. In the above formula (1), the arylaminosulfonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the heterocyclic aminosulfonyl group represented by R include 2-pyridylaminosulfonyl group, 3-pyridylaminosulfonyl group, 4-pyridylaminosulfonyl group, 2-thienylaminosulfonyl group, and 3-thienylaminosulfonyl group. Groups and the like. In the formula (1), the heterocyclic aminosulfonyl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the aryl group represented by R include a phenyl group and a naphthyl group. In the above formula (1), the aryl group represented by R may be substituted with one or more G ₃ .

In the above formula (1), examples of the heterocyclic ring represented by R include 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-thienyl group, and 3-thienyl group. In the formula (1), the heterocyclic ring represented by R may be substituted with one or more G ₃ . Examples of the aryl group include a phenyl group and a naphthyl group.

  Examples of the heterocyclic ring include pyridine, pyridazine, pyrazine, pyrimidine, triazine, tetrazine, furan, thiophene, pyrrole, pyrazole, imidazole, triazole, tetrazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, quinoline, Isoquinoline, cinnoline, phthalazine, quinoxaline, quinazoline, benzofuran, benzothiophene, indole, indazole, benzimidazole, benzotriazole, benzoxazole, benzoisoxazole, benzothiazole, benzoisothiazole, benzoxadiazole, benzothiadiazole, pyrrolidine, tetrahydrofuran , Tetrahydrothiophene, piperidine, tetrahydropyran, or teto Hidorochiopiran, and the like.

In the above formula (1), examples of the C _{1 to} C ₆ alkyl group represented by X include a methyl group and an ethyl group. Here, the C ₁ -C ₆ alkyl group represented by X may be substituted with a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

Examples of the C _{1 to} C ₆ alkoxy group represented by X include a methoxy group, an ethoxy group, and a t-butoxy group. The C ₁ -C ₆ alkoxy group represented by X may be substituted with a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

Examples of the C ₁ -C ₆ alkylthio group represented by X include a methylthio group and an ethylthio group. Further, the C ₁ -C ₆ alkylthio group represented by X may be substituted with a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

  In said formula (1), m shows the integer in any one of 0-4. When m is 0, X is not included in the formula (1), and when m is 1, X is added to any one of the four carbons (C) constituting the phenyl group. Further, when m is 2 or 3, X is added to any two or three of the carbon (C), and when m is 4, X is added to all of the carbon (C).

In the formula (1), examples of the C ₁ -C ₆ alkyl group represented by Y include a methyl group and an ethyl group. Here, the C _{1 to} C ₆ alkyl group represented by Y may be substituted with one or more G ₄ .

G ₄ represents a cyano group, a methoxy group, an ethoxy group, a methylthio group, an ethylthio group, a methylamino group, an ethylamino group, a dimethylamino group, a diethylamino group, a methoxycarbonyl group, or an ethoxycarbonyl group.

In the above formula (1), examples of the C ₁ -C ₆ haloalkyl group represented by Y include a trifluoromethyl group and 2,2,2-trifluoroethyl. In the above formula (1), the haloalkyl group represented by Y may be substituted with one or more G ₄ .

In the above formula (1), the C _{3 to} C ₆ cycloalkyl group represented by Y includes a cyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, a 2,2-dimethylcyclopropyl group, A cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. are mentioned. In the above formula (1), the cycloalkyl group represented by Y may be substituted with one or more G ₄ .

In the above formula (1), as the _C 1 -C ₆ alkoxy group represented by Y, a methoxy group, an ethoxy group, t-butoxy group and the like. In the formula (1), the C _{1 to} C ₆ alkoxy group represented by Y may be substituted with one or more G ₄ .

  In said formula (1), n shows the integer in any one of 0-8. When n is 0, Y is not included in the formula (1). When n is 1, Y is added to any one of the four carbons (C) constituting the piperazine skeleton. When n is 2, Y is added to any one of the carbons (C), or Y is added to any two of the carbons (C). Further, when n is 3, two Ys are added to any one of the carbons (C), and one Y is added to any one of them, or Ys are added to any three of the carbons (C). Add one by one. Further, when n is 4, two Ys are added to any two of the carbons (C), or two Ys are added to any one of the carbons (C), either two One Y is added to each of them, or one Y is added to all of the carbon (C). In addition, when n is 5, two Y are added to any two of the carbon (C), one Y is added to any one, or any one of the carbon (C) Two Ys are added to each, and one Y is added to each of the three. When n is 6, two Y's are added to any three of the carbon (C), or two Y's are added to any two of the carbon (C), either 2 One Y is added to each. When n is 7, two Ys are added to any three of the carbons (C), and one Y is added to any one of the carbons (C). When n is 8, two Ys are added to all of the carbon (C).

  However, two Y on the same carbon can also represent (= O) or (= S), and can also form (C = O) or (C = S). Two Ys may be bonded to each other to represent a carbocyclic or heterocyclic ring. Y may be the same or different.

  Examples of adding Y to the piperazine skeleton in the case where n is 1 to 8 are shown below.

  In said formula (1), p shows the integer in any one of 0-2. When p is 0, oxygen (O) is not added to sulfur (S), and when p is 1, oxygen (O) is added to sulfur (S) and a sulfinyl group (S = O) is added. Form. When p is 2, two oxygens (O) are added to sulfur (S) to form a sulfonyl group (O = S = O).

  In said formula (1), q shows the integer in any one of 0-1. When q is 0, oxygen (O) is not added to nitrogen (N), and when q is 1, oxygen (O) is added to nitrogen (N) to form an N-oxide.

  In said formula (1), r shows the integer in any one of 0-1. When r is 0, oxygen (O) is not added to nitrogen (N), and when r is 1, oxygen (O) is added to nitrogen (N) to form an N-oxide.

  When q and r of the compound represented by the above formula (1) are 0, a salt can be formed. Examples of the salt include a salt of an inorganic acid such as hydrochloride, nitrate, sulfate, phosphate; Examples include salts of organic acids such as salts, lactates, propionates, benzoates and trifluoromethanesulfonates.

  In addition, when an EZ stereoisomer and an optical isomer exist, these isomers are all contained in the substituted phenyl piperazine compound concerning this invention.

  In the substituted phenylpiperazine compound represented by the above formula (1), A, R, X, Y, m, n, p, q, and r satisfy the following conditions to effectively reduce pests. It is more preferable in controlling by application of an amount.

Wherein A is one or more of which can be substituted by _{G 1 C} 1 _{-C 10} alkyl group, one or more may be substituted with _{G 1 C} 2 _{-C 10} alkenyl group, one or more in _{G 1} in optionally substituted _C 2 _{-C 10} alkynyl group, one or more may be substituted with _{G 1 C} 3 _{-C 10} cycloalkyl group, one or more substituted with _{G 1} optionally _C 3 be ~ C ₅ cycloalkenyl group, one or more may be substituted with _{G 1 C} 1 _{-C 10} haloalkyl group, one or more may be substituted with _{G 1 C} 2 _{-C 10} haloalkenyl group or one, shows the above may be substituted with _{G 1 C} 2 _{~C 5} haloalkynyl group.

G ₁ is a cyano group, a C _{3 to} C ₆ cycloalkyl group, a C _{1 to} C ₆ alkoxy group, a C _{1 to} C ₆ alkylthio group, a C _{1 to} C ₆ alkylamino group, or a di C _{2 to} C ₆ alkylamino. group shown, C ₁ -C ₆ alkoxycarbonyl group, one or more aryl group which may be substituted with G ₅ or one or more heterocyclic ring which may be substituted with G _5,.

Wherein R is a hydrogen atom, a cyano group, a formyl group, halocarbonyl group, thioformyl group, one or more optionally substituted with G ₂ C ₁ -C ₂₀ alkyl group, substituted with one or more G ₂ which may _C 2 _{-C 10} alkenyl group, one or more optionally substituted with _{G 2 C 2 ~C 10} alkynyl group, one or more optionally substituted with _{G 3 C 3 ~C 10} cycloalkyl group one or more optionally substituted with _{G 3 C 3 ~C 8} cycloalkenyl group, one or more optionally substituted with _{G 2 C} 1 _{-C 10} alkylcarbonyl group, at least one _{G 2} optionally substituted _C 1 _{-C 10} alkyl thio group, one or more optionally substituted with _{G 2 C} 2 _{-C 10} alkenylcarbonyl group, one or more substituted with _{G 2} good _C 2 be ~ C ₁₀ alkenylene Lucio carbonylation Group, one or more optionally substituted with _{G 2 C} 2 _{-C 10} alkynyl group, one or more optionally substituted with _{G 3 C} 3 _{-C 10} cycloalkyl group, one or more G ₃ optionally substituted _C 3 be _{-C 10} cycloalkylthio group, one or more optionally substituted with _{G 3 C} 3 _{-C 10} cycloalkenyl group, optionally substituted by one or more _{G 2} good _C 1 _{-C 10} alkoxycarbonyl group, one or more substituted with _{G 2 C} 1 may be _{-C 10} alkoxy thiocarbonyl group, one or more optionally substituted with _{G 2 C} 1 _{-C 10} alkyl aminocarbonyl group, one or more substituted with _{G 2 C} 1 may be _{-C 10} alkylamino thiocarbonyl group, one or more _di-C 2 may be substituted with _{G 2} of _{-C 10} alkylamino Carbonyl group, one or more _di-C 2 may be substituted with _{G 2} of _{-C 10} alkylamino thiocarbonyl group, one or more optionally substituted with _{G 3 C 3 ~C 10} cycloalkyl amino carbonyl group, hydroxyl group, one or more optionally substituted with _{G 2 C} 1 _{-C 10} alkoxy group, one or more optionally substituted with _{G 2 C} 1 _{-C 10} alkylamino group, one or more _{G 2} in optionally substituted di _C 2 _{-C 10} alkylamino group, halosulfonyl group, one or more optionally substituted with _{G 2 C} 1 _{-C 10} alkylsulfonyl group, substituted by one or more _{G 2} good _C 2 _{-C 10} alkenylsulfonyl group optionally one or more _{G 3} that is substituted may be _C 3 _{-C 10} cycloalkyl sulfonyl group, one or more substituted with _{G 2} good _C 1 be -C ₁₀ Al Kill aminosulfonyl group, one or more G ₂ substituted by di-C ₂ may be -C ₁₀ alkyl aminosulfonyl group, one or more di-C ₄ may be substituted by G ₂ -C ₁₀ alkenyl aminosulfonyl group one or more _di-C 4 may be substituted by _{G 2 -C 10} alkynyl aminosulfonyl group, one or more _di-C 6 optionally substituted by _{G 3} of _{-C 10} cycloalkyl aminosulfonyl group, one more G ₂ substituted by an optionally tri C ₃ -C ₁₀ alkylsilyl group, one or more G ₃ which may be substituted with a benzyl group, one or more G ₃ which may be substituted with an aryl group , one or more G ₃ which may be substituted with a heterocyclic carbonyl group, one or more substituted with G ₃ which may be arylthiocarbonyl group, one or more substituted with G ₃ heterocyclic ring which may Chiokaru Boniru group, one or more G ₃ which may be substituted with arylcarbonyl group, one or more G ₃ which may be substituted with an aryloxycarbonyl group, one or more substituted with G ₃ may be complex ring oxycarbonyl group, one or more substituted with G ₃ may be aryloxythiocarbonyl group, one or more may be substituted by G ₃ heterocyclyloxy thiocarbonyl group, substituted with one or more G ₃ It is aryl aminocarbonyl group optionally one or more G ₃ which may be substituted with a heterocyclic aminocarbonyl group, one or more G ₃ which may be substituted with arylaminothiocarbonyl group, one or more G ₃ which may be substituted with a heterocyclic amino thiocarbonyl group, one or more substituted with G ₃ arylsulfonyl group which may include one or more heterocyclic sul be substituted with G ₃ Group, one or more may be substituted by G ₃ arylaminosulfonyl group, one or more G ₃ may be substituted by a heterocyclic aminosulfonyl group, it may be substituted with one or more G ₃ An aryl group or a heterocycle optionally substituted with one or more G ₃ is shown.

G ₂ is a halogen atom, a cyano group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkylamino group, or a di C ₂ -C. ₆ alkylamino _group, C 1 -C ₆ alkylsulfinyl _group, C 1 -C ₆ alkylcarbonyl _group, C 3 -C ₆ cycloalkyl _group, C 1 -C ₆ alkoxycarbonyl _group, C 1 -C ₆ alkoxyimino group A C ₂ -C ₆ alkenyloxyimino group, a C ₂ -C ₆ alkynyloxyimino group, a C ₁ -C ₆ haloalkoxyimino group, an aryl group optionally substituted by one or more G ₅ , one or more which may be heterocyclic substituted by G _5, one or more G ₅ which may be substituted with an arylcarbonyl group, one or more G ₅ which may be substituted with a heterocyclic carbonyl group, Other shows one or more optionally substituted aryloxy group G _5.

G ₃ is a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ haloalkyl group, or a C ₃ -C. ₆ cycloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ haloalkylsulfinyl _group, C 1 -C ₆ alkylsulfonyl _group, C 1 -C ₆ haloalkylsulfonyl _group, C 1 -C ₆ alkylamino group, _di-C 2 -C ₆ alkylamino _group, C 2 -C ₆ alkenyl amino _group, C 2 -C _{6 alkynylamino,} C 1 -C ₆ alkylcarbonyl _group, C 1 -C ₆ alkoxycarbonyl _group, C 1 -C ₆ alkylamino Carbonyl _group, C 1 -C ₆ haloalkylcarbonyl aminocarbonyl _group, C 2 -C ₆ alkylcarbonylamino group, one or more _{G 5} with an optionally substituted aryl group, optionally substituted by one or more _{G 5} an aryloxy group, one or more G ₅ with an optionally substituted benzyl group, one or more G ₅ with an optionally substituted benzoyl group, one or more heterocyclic ring which may be substituted with G _5, or it is substituted by one or more G ₅ illustrates a heterocyclic oxy group.

G ₅ is a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ haloalkyl group, or a C ₃ -C. ₆ cycloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ alkylamino group, di-C ₂ -C ₆ alkylamino _group, a C 1 -C ₆ haloalkyl group,
Wherein X is a halogen atom, a cyano group, a nitro group, may be substituted with a halogen atom C ₁ -C ₆ alkyl group, optionally C ₁ -C ₆ alkoxy group optionally substituted by a halogen atom or substituted by a halogen atom, And C ₁ -C ₆ alkylthio groups that may be substituted.

Wherein Y is a halogen atom, an oxygen atom, a sulfur atom, one or more may be substituted by _{G 4 C} 1 -C ₆ alkyl group, one or more substituted with _{G 4 C} 1 may be -C ₆ a haloalkyl group ,, one or more may be substituted by _{G 4 C} 3 _{~C 6} cycloalkyl group, or one or more may be substituted by _{G 4 C} 1 -C ₆ alkoxy group.

  However, two Y on the same carbon can also represent (= O) or (= S), and can also form (C = O) or (C = S). Two Ys may be bonded to each other to represent a carbocyclic or heterocyclic ring. Y may be the same or different.

G ₄ is a cyano group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkylamino group, a di C ₂ -C ₆ alkylamino group, or a C ₁ -C ₆ alkoxy group. A carbonyl group is shown.

  The m represents an integer of 0 to 4, the n represents an integer of 0 to 8, the p represents an integer of 0 to 2, and the q and r are Represents an integer of 0 to 1, and the aryl group is a phenyl group or a naphthyl group.

  The heterocyclic ring is pyridine, pyridazine, pyrazine, pyrimidine, triazine, tetrazine, furan, thiophene, pyrrole, pyrazole, imidazole, triazole, tetrazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, quinoline, isoquinoline , Cinnoline, phthalazine, quinoxaline, quinazoline, benzofuran, benzothiophene, indole, indazole, benzimidazole, benzotriazole, benzoxazole, benzisoxazole, benzothiazole, benzoisothiazole, benzoxiadiazole, pyrrolidine, tetrahydrofuran, Tetrahydrothiophene, piperidine, tetrahydropyran, or tetrahydride Thiopyran.

  Further, in the substituted phenylpiperazine compound represented by the above formula (1), A, R, X, Y, m, n, p, q, and r satisfy the following conditions to effectively prevent pests. It is more preferable in controlling with a low dosage.

Wherein A is one or more of which can be substituted by _{G 1 C} 1 -C ₅ alkyl _groups, C 2 -C ₅ alkenyl _groups, C 2 -C ₅ alkynyl _groups, C 3 -C ₅ cycloalkyl groups, C ₁ -C ₈ haloalkyl group or an _C 2 -C ₈ haloalkenyl group,.

G ₁ represents a cyano group or a C _{3 to} C ₆ cycloalkyl group.

R is a hydrogen atom, a formyl group, a halocarbonyl group, a thioformyl group, a C ₁ -C ₁₈ alkyl group that may be substituted with one or more G ₂ , and a C that is optionally substituted with one or more G _{2. 2} -C ₈ alkenyl group, one or more optionally substituted with _{G 2 C 2} ~C ₈ alkynyl group, one or more optionally _C 3 substituted by _{G 3} of -C ₆ cycloalkyl group, one more _{G 2} which may be substituted, _C 1 -C ₈ alkylcarbonyl group, one or more _C 1 may be substituted by _{G 2} -C ₈ alkyl thio group, substituted with one or more _{G 2} which may _C 2 -C ₈ alkenylcarbonyl group, one or more optionally substituted with _{G 3 C 3 ~C 8} cycloalkyl group, one or more optionally substituted with _{G 3 C 3 ~C 8} A cycloalkylthiocarbonyl group, one or more _{G 2} which may be substituted, _C 1 -C ₈ alkoxycarbonyl group, one or more _C 1 may be substituted by _{G 2} -C ₈ alkylaminocarbonyl group, substituted with one or more _{G 2} which may _C 1 -C ₈ alkylamino thiocarbonyl group, one or more _{G 2} that is substituted di _C 2 may be -C ₈ alkylaminocarbonyl group, one or more which may be di-C substituted with _{G 2 2} -C ₈ alkylaminothiocarbonyl group, a hydroxyl group, a halosulfonyl group, one or more substituted with _{G 2 C} 1 may be -C ₈ alkylsulfonyl group may be substituted by one or more _{G 2} C ₂ -C ₈ alkenylsulfonyl group, one or more _{G 3-substituted C} 3 -C ₈ optionally cycloalkylsulfonyl group, one or more _C 1 may be substituted by _{G 2} -C ₈ alkylamino Ruhoniru group, one or more substituted with G ₂ good di C ₂ -C ₈ alkylaminosulfonyl group optionally, one or more which may be a benzyl group substituted with G _3, substituted by one or more G ₃ good benzoyl group optionally one or more G ₃ which may be substituted with a heterocyclic carbonyl group, one or more G ₃ which may be substituted with a phenyl thio group, substituted with one or more G ₃ also heterocyclic thiocarbonyl group, one or more G ₃ in which may be substituted benzoyloxy group, one or more G ₃ which may be substituted with a phenoxycarbonyl group, substituted with one or more G ₃ also heterocyclic oxycarbonyl group, one or more G ₃ which may be substituted with a phenylamino group, one or more may be substituted by G ₃ heterocyclic aminocarbonyl group, by one or more G ₃ Even if it is replaced Phenyl sulfonyl group, one or more may be substituted by G ₃ heterocyclic sulfonyl group, one or more G ₃ in an optionally substituted phenyl aminosulfonyl group, optionally substituted by one or more G ₃ A good phenyl group, or a heterocyclic ring optionally substituted with one or more G ₃ .

G ₂ is a halogen atom, a cyano group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkylthio group, a C ₁ -C ₄ alkylamino group, or a di C ₂ -C. ₆ alkylamino _group, C 1 -C ₄ alkylsulfinyl _group, C 1 -C ₄ alkylcarbonyl _group, C 3 -C ₆ cycloalkyl _group, C 1 -C ₆ alkoxycarbonyl _group, C 1 -C ₄ alkoxyimino group , C ₂ -C ₄ alkynyloxy imino group, one or more G ₅ with a phenyl group which may be substituted with one or more heterocyclic ring which may be substituted with G _5, substituted by one or more G ₅ 1 represents an optionally substituted benzoyl group, or a phenoxy group optionally substituted by one or more G ₅ .

G ₃ is a halogen atom, a cyano group, a nitro group, a C ₁ -C ₄ alkyl group, a C ₂ -C ₅ alkenyl group, a C ₂ -C ₅ alkynyl group, a C ₁ -C ₄ haloalkyl group, or a C ₃ -C. ₆ cycloalkyl group, C ₁ -C ₄ alkoxy group, C ₁ -C ₄ haloalkoxy group, C ₁ -C ₄ alkylthio group, C ₁ -C ₄ haloalkylthio group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ haloalkylsulfinyl _group, C 1 -C ₄ alkylsulfonyl _group, C 1 -C ₄ haloalkylsulfonyl _group, C 1 -C ₆ alkylamino group, _di-C 2 -C ₆ alkylamino _group, C 2 -C ₆ alkenyl amino _group, C 2 -C ₄ alkynyl amino _groups, C 1 -C ₆ alkylcarbonyl _group, C 1 -C ₆ alkoxycarbonyl _group, C 1 -C ₆ alkylamino Carbonyl group, C ₁ -C ₆ haloalkylcarbonyl aminocarbonyl group, one or more G ₅ which may be substituted with a phenyl group, one or more G ₅ which may be substituted with a phenoxy group, with one or more G ₅ optionally substituted benzoyl group, one or more G ₅ heterocyclic ring which may be substituted by or one or more substituted with G ₅ may be a heterocyclic oxy group,.

G ₅ is a halogen atom, a cyano group, a nitro group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₄ alkoxy group, a C _1- A C ₄ haloalkoxy group, a C ₁ -C ₄ alkylthio group, or a C ₁ -C ₄ haloalkylthio group;

Wherein X represents a halogen atom, a cyano group or optionally substituted by a halogen atom C ₁ -C ₄ alkyl group.

Wherein Y represents a halogen atom, an oxygen _atom, a C 3 -C ₆ cycloalkyl group or a _C 1 -C ₄ alkyl group. However, two Y on the same carbon can also represent (= O) and can also form (C = O).

  The m represents an integer of 1 to 3, the n represents an integer of 0 to 4, the p represents an integer of 0 to 2, and the q and r are , An integer from 0 to 1 is shown.

  The heterocyclic ring is pyridine, pyrimidine, furan, thiophene, pyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, quinoline, isoquinoline, indole, benzoisothiazole, benzothiadiazole, tetrahydrofuran, tetrahydrothiophene, piperidine , Tetrahydropyran, or tetrahydrothiopyran.

  Further, in the substituted phenylpiperazine compound represented by the above formula (1), A, R, X, Y, m, n, p, q, and r satisfy the following conditions to effectively prevent pests. It is more preferable when controlling with a low dosage.

Wherein _A represents a C 2 -C ₄ haloalkyl group.

R is a hydrogen atom, a formyl group, a chlorocarbonyl group, a thioformyl group, a C ₁ -C ₁₅ alkyl group that may be substituted with one or more G ₂ , and a C that is optionally substituted with one or more G _{2. 2} -C ₅ alkenyl group, one or more optionally substituted with _{G 2 C 2 ~C 5} alkynyl group, one or more optionally substituted with _{G 2 C} 1 -C ₆ alkylcarbonyl group, one more optionally substituted with _{G 2 C} 1 -C ₆ alkylthiocarbonyl group, one or more optionally substituted with _{G 2 C 2 ~C 6} alkenyl group, substituted with one or more _{G 3} C ₃ -C ₈ cycloalkylcarbonyl group, C ₃ -C ₈ cycloalkylthiocarbonyl group optionally substituted by one or more G ₃ , C ₁ -C optionally substituted by one or more G _{2 6} alkoxycarbonyl group One or more substituted with _{G 2 C} 1 may be -C ₅ alkylaminocarbonyl group, one or more optionally substituted with _{G 2 C} 1 -C ₅ alkylamino thiocarbonyl group, one or more G di C ₂ may be substituted by ₂ -C ₅ alkylaminocarbonyl group, one or more may be substituted by G ₂ di C ₂ -C ₅ alkylaminothiocarbonyl group, a hydroxyl group, chlorosulfonyl group, 1 one or more substituted with _{G 2 C} 1 may be -C ₆ alkylsulfonyl group, one or more optionally substituted with _{G 2 C 2} ~C ₆ alkenyl sulfonyl group is substituted with one or more _{G 3} which may be _C 3 -C ₈ cycloalkylsulfonyl group, one or more optionally substituted with _{G 2 C} 1 -C ₈ alkylaminosulfonyl group, one or more _{G 2} good di _{C 2} may be substituted with ~C Alkylaminosulfonyl group, one or more optionally substituted benzyl group in G _3, one or more may benzoyl group optionally substituted by G _3, one or more heterocyclic carbonyl optionally substituted with G ₃ group, one or more G ₃ which may be substituted with a phenyl thio group, one or more G ₃ in which may be substituted benzoyloxy group, one or more G ₃ which may be substituted with a phenoxycarbonyl group one or more substituted with G ₃ may be phenylaminocarbonyl group, one or more G ₃ which may be phenylsulfonyl group substituted with one or more may be substituted by G ₃ heterocyclic sulfonyl group indicates one or more phenyl group which may be substituted with G ₃ or one or more heterocyclic ring which may be substituted with G _3,.

G ₂ represents a halogen atom, a cyano group, a C _{3 to} C ₆ cycloalkyl group, a C _{1 to} C ₄ alkoxy group, a C _{1 to} C ₄ alkylthio group, a C _{1 to} C ₄ alkylsulfinyl group, or a C _{1 to} C _4. alkylcarbonyl _group, substituted with C 3 -C ₆ cycloalkyl _group, C 1 -C ₄ alkoxycarbonyl _group, C 1 -C ₄ alkoxyimino _group, C 2 -C ₄ alkynyloxy imino group, one or more _{G 5} phenyl group which may be one or more heterocyclic ring which may be substituted with G _5, which may be substituted one or more or a benzoyl group or at least one G ₅ be substituted with G _5-phenoxy Indicates a group.

G ₃ is a halogen atom, a cyano group, a nitro group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group, a C _1- C ₄ alkylthio group, C ₁ -C ₄ haloalkylthio group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ haloalkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, C ₁ -C ₄ haloalkylsulfonyl group, C ₁ -C ₄ alkylamino group, _di-C 2 -C ₄ alkylamino _group, C 1 -C ₄ alkoxycarbonyl _group, C 1 -C ₄ alkylaminocarbonyl _group, C 1 -C ₄ halo alkylaminocarbonyl group, _{C 2} -C ₆ alkylcarbonylamino group, one or more G ₅ with optionally substituted phenyl group, optionally substituted by one or more G ₅ There phenoxy group, one or more G ₅ heterocyclic ring which may be substituted by or one or more substituted with G ₅ may be a heterocyclic oxy group,.

G ₅ represents a halogen atom, a cyano group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, or a C ₁ -C ₄ alkoxy group.

Wherein X represents a halogen atom, a cyano group, or a _C 1 -C ₄ alkyl group.

Wherein Y represents an oxygen _atom, C 1 -C ₄ alkyl or _C 3 -C ₆ cycloalkyl group,. However, two Y on the same carbon can also represent (= O) and can also form (C = O).

  The m represents an integer of 1 to 2, the n represents an integer of 0 to 3, the p represents an integer of 0 to 2, and the q and r are , An integer from 0 to 1 is shown.

  The heterocyclic ring is pyridine, thiophene, triazole, oxazole, thiazole, quinoline, isoquinoline, indole, benzisothiazole, benzothiadiazole, tetrahydrofuran, piperidine, tetrahydropyran, or tetrahydrothiopyran.

  Further, in the substituted phenylpiperazine compound represented by the above formula (1), A, R, X, Y, m, n, p, q, and r satisfy the following conditions to effectively prevent pests. Most suitable for controlling with a low dosage.

  A represents a 2,2,2-trifluoroethyl group.

Wherein R is a hydrogen atom, a formyl group, one or more optionally substituted with _{G 2 C} 1 _{-C 15} alkyl group, a propargyl group, one or more substituted with _{G 2 C} 1 may be -C ₆ alkylcarbonyl group, one or more substituted with _{G 2 C} 1 may be -C ₆ alkyl thiocarbonyl group, one or more optionally substituted with _{G 2 C 2} ~C ₆ alkenyl group, one or more G ₃ in optionally substituted _C 3 be -C ₈ cycloalkyl group, one or more optionally substituted with _{G 3 C} 3 -C ₈ cycloalkylthio group, substituted with one or more _{G 2} which may _C 1 -C ₆ alkoxycarbonyl group, one or more _{G 2} substituted by _C 1 may be -C ₅ alkylaminocarbonyl group, _C 1 may be substituted by one or more _{G 2} -C ₅ Alkylaminothio Carbonyl group, a dimethylaminocarbonyl group, dimethylamino thiocarbonyl group, one or more substituted with G ₂ C ₁ may be -C ₆ alkylsulfonyl group, one or more substituted with G ₃ optionally C ₃ be ~ C ₆ cycloalkylsulfonyl group, di-C ₂ -C ₄ alkylaminosulfonyl group optionally substituted with one or more G ₂ , benzyl group optionally substituted with one or more G ₃ , one or more G ₃ which may be substituted with a benzoyl group, one or more G ₃ is substituted with heterocyclic carbonyl group which may include one or more G ₃ which may be substituted with a phenyl thio group, one or more G ₃ in an optionally substituted phenoxycarbonyl group, one or more G ₃ in which it may be substituted phenylsulfonyl group, one or more may be substituted by G ₃ heterocyclic sulfonyl group.

Wherein G ₂ is a halogen atom, a cyano group, a cyclopropyl group, a methoxycarbonyl group, a methoxy group, a methylthio group, one or more optionally substituted phenyl group G _5, substituted by one or more G ₅ Or a benzoyl group optionally substituted with one or more G ₅ .

G ₃ is a halogen atom, a cyano group, a methyl group, a trifluoromethyl group, a methoxy group, a methylthio group, a trifluoromethoxy group, a trifluoromethylthio group, a phenyl group that may be substituted with one or more G ₅ , one or more G ₅ which may be substituted with a phenoxy group, one or more G ₅ heterocyclic ring which may be substituted by or one or more substituted with G ₅ may be a heterocyclic oxy group,.

G ₅ represents a halogen atom, a methyl group, a trifluoromethyl group, or a methoxy group.

  X represents a halogen atom, a cyano group, or a methyl group, m represents 2, n represents 0, p represents an integer of 0 to 1, q and r represents 0, and the aryl group is a phenyl group.

  The heterocyclic ring is pyridine, thiophene, triazole, thiazole, oxazole, quinoline, tetrahydrofuran, or tetrahydropyran.

  Next, although the specific example of this invention compound represented by General formula (1) is described in Table 1-1-Table 3-11, this invention compound is not limited to these compounds. In addition, these compounds include compounds including optical isomers, E isomers, and Z isomers. The compound number will be referred to in the following description.

In addition, the following notation in a table | surface represents each applicable group as follows.
“Me” is a methyl group, “Et” is an ethyl group, “Pr” is a propyl group, “n-Pr” is a normal propyl group, “i-Pr” is an isopropyl group, “Bu” is a butyl group, “n-Pr” “Bu” is a normal butyl group, “Pen” is a pentyl group, “n-Pen” is a normal pentyl group, “Hex” is a hexyl group, “n-Hex” is a normal hexyl group, “Hep” is a heptyl group, “s -Bu "is a secondary butyl group," i-Bu "is an isobutyl group," t-Bu "is a tertiary butyl group," c-Pr "is a cyclopropyl group," c-Bu "is a cyclobutyl group," c-Bu ""Pen" is a cyclopentyl group, "neo-Pen" is a neopentyl group, "c-Hex" is a cyclohexyl group, "c-Hep" is a cycloheptyl group, "THF" is a tetrahydrofuryl group, "THP" is a teto group A lahydropyranyl group, “Ph” represents a phenyl group, “Bn” represents a benzyl group, and “Py” represents a pyridyl group. “H” represents no substitution. “On TLC” and “under TLC” indicate isomers.

X ₁ , X ₂ , X ₃ and X ₄ represent X specifying the substitution position on the benzene ring, and Y ₁ , Y ₂ , Y ₃ and Y ₄ represent Y specifying the substitution position on the piperazine ring. However, Y ₁ and Y ₄ can also represent two Ys. For example, (= O), (= S), (Me ₂ ), (F ₂ ), ((CH ₂ ) ₂ ), ((CH ₂ ) ₃ ), and the like can be represented.

  Table 1-1 to Table 1-29 represent compounds of formula (1) with A = 2,2,2-trifluoroethyl groups and n = 0. Tables 2-1 to 2-9 represent compounds of formula (1) where n = 0, q = 0 and r = 0. Tables 3-1 to 11-11 represent compounds of the formula (1) in which A = 2,2,2-trifluoroethyl group, q = 0 and r = 0.

  Although the compound concerning this invention represented by following General formula (1) can be manufactured in accordance with the manufacturing method shown below, it is not limited to these methods.

  (In the above formula, A, X, Y, R, m, n, p, q, and r have the same meaning as described above, except when q = 0 and r = 0.)

  The compound (2) according to the present invention can be produced, for example, by reacting the compound represented by the general formula (1) with copper iodide in the presence of a base.

  Examples of the base used in this reaction include bases such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, and pyridine. Triethylamine, diisopropylethylamine and the like are preferable.

  Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and cycloheptane Or a mixed solvent thereof. Preferred is tetrahydrofuran.

  (In the above formula, A, X, Y, R, m, n, p, q, and r have the same meaning as described above, except when p = 0, q = 0, and r = 0.)

  The compound (1) concerning this invention can be manufactured by making the compound and oxidant which are represented by the said General formula (3) react, for example.

  Examples of the oxidizing agent used in this reaction include hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, oxone (OXONE, trade name of EI DuPont; potassium hydrogen peroxosulfate), N -Chlorosuccinimide, N-bromosuccinimide, tert-butyl dichlorite, sodium hypochlorite and the like. Preferred is m-chloroperbenzoic acid.

  Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone and sulfolane; alcohols such as methanol, ethanol and isopropyl alcohol; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; pentane and hexane Aliphatic hydrocarbons such as cyclohexane and cycloheptane; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; acetic acid, water, or a mixed solvent thereof. Preferred are dichloromethane, chloroform and the like.

(In the above formula, Xa represents _a halogen atom, A, Y, R, m, and n have the same meaning as described above, and m ≠ 0.)

  The compound (5) according to the present invention can be produced, for example, by reacting the compound represented by the general formula (4) with a halogenating agent.

  Examples of the halogenating agent used in this reaction include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, sulfuryl chloride, thionyl chloride, and the like. Preferred are bromine, iodine, sulfuryl chloride and the like.

  Examples of the solvent used in this reaction include halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and mixed solvents thereof. Preferred is dichloromethane.

  (In the above formula, L represents a leaving group such as a halogen atom, an alkylsulfonyloxy group, a haloalkylsulfonyloxy group, and an arylsulfonyloxy group, and A, X, Y, R, m, and n have the same meaning as described above. .)

  The compound (3) according to the present invention can be produced, for example, by reacting the compound represented by the general formula (6) and the compound represented by the general formula (7) in the presence of a base. it can.

  The raw material represented by the general formula (7) is a known compound, and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Alternatively, it can be produced from a commercially available reagent according to a known method described in Experimental Chemistry Course, Organic Synthesis, etc.

  Examples of the base used in this reaction include bases such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, and pyridine. Preferred are potassium carbonate and triethylamine.

  Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide and sulfolane; Halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; Fats such as pentane, hexane, cyclohexane and cycloheptane Group hydrocarbons or a mixed solvent thereof. N, N-dimethylformamide, dichloromethane and the like are preferable.

(In the above formula, Z is an oxygen atom or a sulfur atom, R _a is one or more of which may be substituted with G ₂ C ₁ -C ₂₀ alkyl group may be substituted by one or more G ₂ C ₂ -C ₂₀ alkenyl group, one or more optionally substituted with _{G 2 C 2 ~C 20} alkynyl group, one or more optionally substituted with _{G 3 C 3 ~C 20} cycloalkyl group, 1 one or more of which may be substituted benzyl group G _3, one or more optionally substituted aryl groups G _3, shows the heterocyclic ring which may be substituted by one or more G _3, a, X, Y, m, and n have the same meaning as described above.)

  For example, the compound (9) according to the present invention is obtained by reacting the compound represented by the general formula (6) with the compound represented by the general formula (8) in the presence or absence of a base. Can be manufactured.

  The raw material represented by the general formula (8) is a known compound, and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Alternatively, it can be produced from a commercially available reagent according to a known method described in Experimental Chemistry Course, Organic Synthesis, etc.

  Examples of the base used in this reaction include bases such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, and pyridine. Triethylamine, diisopropylethylamine and the like are preferable.

  Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide and sulfolane; Halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; Fats such as pentane, hexane, cyclohexane and cycloheptane Group hydrocarbons or a mixed solvent thereof. Preferred are tetrahydrofuran, toluene and the like.

(In the formula, _{R a} 'is hydrogen atom, one or more optionally substituted with _{G 2 C} 1 _{-C 20} alkyl group, one or more optionally substituted with _{G 2 C 2 ~C 20} alkenyl group, one or more optionally substituted with _{G 2 C 2 ~C 20} alkynyl group, one or more optionally substituted with _{G 3 C 3 ~C 20} cycloalkyl group, by one or more _{G 3} optionally substituted benzyl group, one or more G ₃ in optionally substituted aryl group, one or more heterocyclic ring which may be substituted with _{G 3, a, X, Y} , m, n, R _a has the same meaning as described above, and R _a and R _a ′ can be bonded to each other to represent a heterocyclic ring.

  As shown in Reaction Step 6-2, the compound (12) according to the present invention comprises a compound represented by the general formula (10) and a compound represented by the general formula (11) in the presence of a base or It can be produced by reacting in the absence.

  The raw material represented by the general formula (11) is a known compound, and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Alternatively, it can be produced from a commercially available reagent according to a known method described in Experimental Chemistry Course, Organic Synthesis, etc.

  Examples of the base used in the reaction step 6-2 include, for example, bases such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, and pyridine. Is mentioned. Preferred is triethylamine.

  Examples of the solvent used in the reaction step 6-2 include ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; acetonitrile, N, N-dimethylformamide, N , N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane and other aprotic polar solvents; Dichloromethane, chloroform, 1,2-dichloroethane and other halogenated hydrocarbons; Pentane, hexane, cyclohexane, cyclo Aliphatic hydrocarbons such as heptane or a mixed solvent thereof. Preferred are dichloromethane, toluene and the like.

  The compound represented by the general formula (10) is reacted with phosgene, diphosgene or triphosgene in the presence of the compound represented by the general formula (6) and a base as in the reaction step 6-1. Can be manufactured.

  Examples of the base used in the reaction step 6-1 include bases such as potassium carbonate, sodium carbonate, triethylamine, diisopropylethylamine, and pyridine. Preferred are triethylamine, pyridine and the like.

  Examples of the solvent used in the reaction step 6-1 include ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; dichloromethane, chloroform, 1,2-dichloroethane, and the like. Halogenated hydrocarbons; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, cycloheptane, or a mixed solvent thereof. Preferred is toluene.

(In the formula, _{R b} is one or more of which may be substituted with _{G 2 C} 1 _{-C 20} alkyl group, one or more optionally substituted with _{G 2 C 2 ~C 20} alkenyl group, one C ₂ -C ₂₀ alkynyl group optionally substituted with G ₂ or more, C ₃ -C ₂₀ cycloalkyl group optionally substituted with one or more G ₃ , or substituted with one or more G ₂ A good C ₁ -C ₂₀ alkoxy group, a benzyl group optionally substituted with one or more G ₃ , an aryl group optionally substituted with one or more G ₃ , or substituted with one or more G ₃ A good heterocyclic ring is shown, and A, X, Y, m, and n have the same meaning as described above.)

  The compound (14) according to the present invention can be produced, for example, by reacting the compound represented by the general formula (13) with a Lawson reagent.

  Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and cycloheptane Or a mixed solvent thereof. Preferred are tetrahydrofuran, toluene and the like.

(In the above formula, A, X, Y, m, n and R _b have the same meaning as described above.)

  The compound (13) according to the present invention can be produced, for example, by reacting the compound represented by the general formula (6) and the compound represented by the general formula (15) in the presence of a base. .

  The raw material represented by the general formula (15) is a known compound, and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Alternatively, it can be produced from a commercially available reagent according to a known method described in Experimental Chemistry Course, Organic Synthesis, etc.

  Examples of the base used in this reaction include bases such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, and pyridine. Preferred is triethylamine.

  Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide and sulfolane; Halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; Fats such as pentane, hexane, cyclohexane and cycloheptane Group hydrocarbons or a mixed solvent thereof. Preferred is dichloromethane.

(In the formula, _{R c} is one or more _{G 2} which may be substituted with _C 1 _{-C 20} alkyl group, one or more optionally substituted with _{G 2 C 2 ~C 20} alkenyl group, one more optionally substituted with _{G 2 C 2 ~C 20} alkynyl group, one or more optionally substituted with _{G 3 C 3 ~C 20} cycloalkyl group, optionally substituted by one or more _{G 3} good C ₃ -C ₂₀ cycloalkenyl group, one or more G ₃ in which may be substituted benzyl group, one or more G ₃ in optionally substituted aryl group, substituted with one or more G ₃ And A, X, Y, m, and n have the same meaning as described above.

  The compound (17) according to the present invention is produced, for example, by reacting the compound represented by the general formula (6) and the compound represented by the general formula (16) in the presence of a condensing agent and a base. be able to.

  The raw material represented by the general formula (16) is a known compound, and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Alternatively, it can be produced from a commercially available reagent according to a known method described in Experimental Chemistry Course, Organic Synthesis, etc.

  Examples of the condensing agent used in this reaction include N, N′-dicyclohexylcarbodiimide, N, N′-diisopropylcarbodiimide, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide, and 1,1′-carbonyldiimide. Examples include condensing agents such as imidazole, 1H-benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate. Preferred are 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide, 1,1'-carbonyldiimidazole, 1H-benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate.

  Examples of the base used in this reaction include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine and the like. Of the base. Triethylamine, diisopropylethylamine and the like are preferable.

  Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide and sulfolane; Halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; Fats such as pentane, hexane, cyclohexane and cycloheptane Group hydrocarbons or a mixed solvent thereof. Preferred are dichloromethane, N, N-dimethylformamide and the like.

(In the above formula, A, X, Y, m, n, and R _c have the same meaning as described above.)

  The compound (19) according to the present invention can be produced, for example, by reacting the compound represented by the general formula (6) with the compound represented by the general formula (18) in the presence of a base. .

  The raw material represented by the general formula (18) is a known compound, and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Alternatively, it can be produced from a commercially available reagent according to a known method described in Experimental Chemistry Course, Organic Synthesis, etc.

  Examples of the base used in this reaction include bases such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, and pyridine. Preferred is triethylamine.

  Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide and sulfolane; Halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; Fats such as pentane, hexane, cyclohexane and cycloheptane Group hydrocarbons or a mixed solvent thereof. Preferred is dichloromethane.

(In the formula, _{R c} 'is a hydrogen atom, one or more optionally substituted with _{G 2 C} 1 _{-C 20} alkyl group, one or more optionally substituted with _{G 2 C 2 ~C 20} alkenyl group, one or more optionally substituted with _{G 2 C 2 ~C 20} alkynyl group, one or more optionally substituted with _{G 3 C 3 ~C 20} cycloalkyl group, by one or more _{G 3} optionally substituted C ₃ -C ₂₀ cycloalkenyl group, one or more G ₃ in which may be substituted benzyl group, one or more G ₃ in optionally substituted aryl group, one or more G ₃ And A, X, Y, m, n, and R _c have the same meaning as described above, and R _c and R _c ′ may be bonded to each other to represent a heterocyclic ring. .)

  As shown in the above reaction step 11-2, the compound (22) according to the present invention comprises a compound represented by the general formula (20) and a compound represented by the general formula (21) in the presence of a base or It can be produced by reacting in the absence.

  The raw material represented by the general formula (21) is a known compound, and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Alternatively, it can be produced from a commercially available reagent according to a known method described in Experimental Chemistry Course, Organic Synthesis, etc.

  Examples of the base used in the reaction step 11-2 include, for example, potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine and the like. Is mentioned. Preferred is triethylamine.

  Examples of the solvent used in the reaction step 11-2 include ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; acetonitrile, N, N-dimethylformamide, N , N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane and other aprotic polar solvents; Dichloromethane, chloroform, 1,2-dichloroethane and other halogenated hydrocarbons; Pentane, hexane, cyclohexane, cyclo Aliphatic hydrocarbons such as heptane or a mixed solvent thereof. Preferred is tetrahydrofuran.

  The compound represented by the general formula (20) can be produced by reacting with the sulfuryl chloride in the presence of the compound represented by the general formula (6) and a base as in the reaction step 11-1. it can.

  Examples of the base used in the reaction step 11-1 include bases such as potassium carbonate, sodium carbonate, triethylamine, diisopropylethylamine, and pyridine. Preferred is triethylamine.

  Examples of the solvent used in the reaction step 11-1 include ethers such as diethyl ether, tetrahydrofuran, and dioxane; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; pentane, hexane, cyclohexane, and cycloheptane. Aliphatic hydrocarbons such as these, or a mixed solvent thereof. Preferred is dichloromethane.

(In the formula, R _d is one or more G ₃ in optionally substituted aryl group, one or more heterocyclic ring which may be substituted with _{G 3, A, X, Y} , m, n, L has the same meaning as described above.)

  The compound (24) according to the present invention is disclosed in, for example, Tetrahedron Letters, 2002, p. 3359, Bioorganic & Medicinal Chemistry Letters, 2001, p. In accordance with the method described in 1375 and the like, the compound represented by the above general formula (6) and the compound represented by the above general formula (23) are converted in the presence or absence of a transition metal catalyst, a base, and a ligand. , Can be produced by reacting.

  The raw material represented by the general formula (23) is a known compound, and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Alternatively, it can be produced from a commercially available reagent according to a known method described in Experimental Chemistry Course, Organic Synthesis, etc.

  Examples of the transition metal catalyst used in this reaction include palladium-activated carbon, palladium acetate, dichlorobis (triphenylphosphine) palladium, dichlorobis (tri-ortho-tolylphosphine) palladium, tetrakis (triphenylphosphine) palladium, tetrakis ( Examples include palladium compounds such as tri-ortho-tolylphosphine) palladium and tris (dibenzylideneacetone) palladium, and nickel compounds such as bis (triphenylphosphine) nickel chloride and tetrakis (triphenylphosphine) nickel. Preferred is tris (dibenzylideneacetone) palladium.

  Examples of the base used in this reaction include bases such as sodium tert-butoxide, potassium tert-butoxide, sodium hydrogen carbonate, sodium carbonate, potassium carbonate, triethylamine, diisopropylethylamine, and pyridine. Sodium tert-butoxide is preferred.

  Examples of the ligand used in this reaction include tri-tert-butylphosphine, 2- (di-tert-butylphosphino) biphenyl, 1,1′-bis (diphenylphosphino) ferrocene, 4,5- Bis (diphenylphosphino) -9,9-dimethylxanthene, 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl, 2,2′-bis (diphenylphosphino) -1,1′-binaphthyl and the like It is done. Preferred are 2- (di-tert-butylphosphino) biphenyl, 2,2'-bis (diphenylphosphino) -1,1'-binaphthyl and the like.

  Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Examples include aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and mixed solvents thereof. Preferred is toluene.

(In the formula, _{R e} is one or more optionally substituted with _{G 2 C} 1 _{-C 20} alkyl group, one or more optionally substituted with _{G 2 C 2 ~C 20} alkenyl group, one more optionally substituted with _{G 2 C 2 ~C 20} alkynyl group, one or more optionally substituted with _{G 3 C 3 ~C 20} cycloalkyl group, optionally substituted by one or more _{G 3} good C ₃ -C ₂₀ cycloalkenyl group, one or more G ₃ in optionally substituted aryl group, one or more heterocyclic ring which may be substituted by G _3, R e _'is hydrogen atom, 1 one or more of which may be substituted with _{G 2 C} 1 _{-C 20} alkyl group, one or more optionally substituted with _{G 2 C 2 ~C 20} alkenyl group, optionally substituted by one or more _{G 2} good _C 2 _{-C 20} alkynyl group, one or more optionally substituted with _{G 3 C 3 ~C 20} Black alkyl group, one or more optionally substituted with G ₃ C ₃ ~C ₂₀ cycloalkyl group, one or more G ₃ in optionally substituted aryl group, substituted with one or more G ₃ A, X, Y, m, and n have the same meaning as described above, and R _e and R _e ′ are bonded to each other to represent a carbocycle or a heterocycle.

  The compound (26) according to the present invention can be produced, for example, by reacting the compound represented by the general formula (6) and the compound represented by the general formula (25) in the presence of a reducing agent. .

  The raw material represented by the general formula (25) is a known compound, and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Alternatively, it can be produced from a commercially available reagent according to a known method described in Experimental Chemistry Course, Organic Synthesis, etc.

  Examples of the reducing agent used in this reaction include reducing agents such as sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride and the like. Preferred is sodium triacetoxyborohydride and the like.

  Examples of the solvent used in this reaction include ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; halogenated carbonization such as dichloromethane, chloroform, and 1,2-dichloroethane. Hydrogens: aliphatic hydrocarbons such as pentane, hexane, cyclohexane, cycloheptane or a mixed solvent thereof. Preferred are dichloromethane, 1,2-dichloroethane and the like.

  (In the above formula, A, X, Y, m, n, and L have the same meaning as described above.)

  The compound (6) according to the present invention is disclosed in, for example, Tetrahedron Letters, 2005, p. According to the method described in 7921 and the like, the compound represented by the general formula (27) and the compound represented by the general formula (28) are produced by heating in the absence of a solvent or in the presence of a solvent. Can do.

  The raw material represented by the general formula (28) is a known compound and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Alternatively, it can be produced from a commercially available reagent according to a known method described in Experimental Chemistry Course, Organic Synthesis, etc.

  Solvents used in this reaction include, for example, ethers such as tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N -Aprotic polar solvents such as methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; alcohols such as methanol, ethanol, isopropyl alcohol, ethylene glycol, diethylene glycol, triethylene glycol, diethylene glycol monomethyl ether, or mixed solvents thereof . Preferred are diethylene glycol monomethyl ether and N-methyl-2-pyrrolidone.

(In the formula, _{R f} is _C 1 _{-C 20} alkyl _group, C 2 _{-C 20} alkenyl _group, C 1 _-C indicates like ₂₀ haloalkyl group, _{X a} represents a hydrogen atom or the like, a halogen atom, A, X , Y, m, and L have the same meaning as described above.)

  Compound (37) according to the present invention can be produced, for example, according to the method described in Green's Protective Groups in Organic Synthesis and the like. The method is obtained by reacting the compound represented by the general formula (34) with the chloroformate represented by the general formula (35) as in the reaction step 15-4. In this method, the compound represented by the general formula (36) is produced by heating to reflux in the absence of a solvent or in the presence of a solvent as in the above reaction step 15-5.

  The solvent used in the reaction step 15-5 is, for example, ethers such as diethyl ether, tetrahydrofuran, dioxane; acetonitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl Examples include aprotic polar solvents such as sulfoxide and sulfolane; alcohols such as methanol, ethanol and isopropyl alcohol, or mixed solvents thereof. Preferred is methanol.

  Examples of the solvent used in the reaction step 15-4 include ethers such as diethyl ether, tetrahydrofuran, and dioxane; halogenated hydrocarbons such as dichloromethane, chloroform, dichloroethane, and mixed solvents thereof. Preferred is dichloromethane.

  The compound represented by the general formula (34) is produced by heating and refluxing the compound represented by the general formula (33) in the absence of a solvent or in the presence of a solvent, as shown in the reaction step 15-3. can do.

  Examples of the solvent used in the reaction step 15-3 include aprotic polar solvents such as acetonitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, and sulfolane; Examples thereof include alcohols such as methanol, ethanol, isopropyl alcohol, 1-butanol and ethylene glycol monomethyl ether, or mixed solvents thereof. N-methyl-2-pyrrolidone, ethylene glycol monomethyl ether and the like are preferable.

  The production intermediate represented by the general formula (33) is represented by the production intermediate represented by the general formula (31) and the general formula (32) as shown in the reaction step 15-2. Can be produced by reacting the compound in the presence of a reducing agent.

  The raw material represented by the general formula (32) is a known compound, and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Alternatively, it can be produced from a commercially available reagent according to a known method described in Experimental Chemistry Course, Organic Synthesis, etc.

  Examples of the reducing agent used in the reaction step 15-2 include reducing agents such as sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride, and the like. Preferred is sodium triacetoxyborohydride and the like.

  Examples of the solvent used in the reaction step 15-2 include ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; dichloromethane, chloroform, 1,2-dichloroethane, and the like. Halogenated hydrocarbons; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, cycloheptane, or a mixed solvent thereof. Preferred are dichloromethane, 1,2-dichloroethane and the like.

  The production intermediate represented by the general formula (31) includes a compound represented by the general formula (29) and a benzaldehyde represented by the general formula (30) as shown in the reaction step 15-1. The derivative can be produced by reacting in the presence of a reducing agent.

  Examples of the reducing agent used in the reaction step 15-1 include reducing agents such as sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride, and the like. Preferred is sodium triacetoxyborohydride and the like.

  Examples of the solvent used in the reaction step 15-1 include ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; dichloromethane, chloroform, 1,2-dichloroethane, and the like. Halogenated hydrocarbons; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, cycloheptane, or a mixed solvent thereof. Preferred are dichloromethane, 1,2-dichloroethane and the like.

(In the above formula, L ₁ and L ₂ represent a leaving group such as a halogen atom, an alkylsulfonyloxy group, a haloalkylsulfonyloxy group, an arylsulfonyloxy group, n represents an integer of 0 to 4, and A , X, Y, and m have the same meaning as described above.)

  The compound (40) according to the present invention is described in, for example, Chemical & Pharmaceutical Bulletin, 2002, p. In accordance with the method described in 453 and the like, the compound represented by the above general formula (27) is reacted with oxazolidine-2-one, and the obtained production intermediate represented by the above general formula (29) is obtained. It can be produced by reacting the compound represented by the general formula (39) in the presence of a base.

  The raw material represented by the general formula (39) is a known compound, and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Alternatively, it can be produced from a commercially available reagent according to a known method described in Experimental Chemistry Course, Organic Synthesis, etc.

  Examples of the base used in the reaction step 16-2 include bases such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, and pyridine. It is done. Preferred is triethylamine.

  Examples of the solvent used in the reaction step 16-2 include ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; acetonitrile, N, N-dimethylformamide, N , N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane and other aprotic polar solvents; Dichloromethane, chloroform, 1,2-dichloroethane and other halogenated hydrocarbons; Pentane, hexane, cyclohexane, cyclo Aliphatic hydrocarbons such as heptane or a mixed solvent thereof. Preferred is dichloromethane.

  Examples of the solvent used in the reaction step 16-1 include aprotic polar solvents such as acetonitrile, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, and sulfolane; Examples thereof include alcohols such as methanol, ethanol, isopropyl alcohol, 1-butanol and ethylene glycol monomethyl ether, or mixed solvents thereof. N-methyl-2-pyrrolidone, ethylene glycol monomethyl ether and the like are preferable.

  (In the above formula, PG represents a protecting group such as an alkylcarbonyl group, a haloalkylcarbonyl group, and an arylcarbonyl group, and A, X, m, and L have the same meaning as described above.)

  The production intermediate represented by the general formula (27) is described in, for example, JP-A-60-79959, Chemische Berichte, 1912, P.A. It can be produced according to a known method described in 1495 and the like.

  The starting material represented by the general formula (41) is a known compound, and can be obtained from Tokyo Chemical Industry Co., Ltd.

  The production intermediate represented by the general formula (43) includes a compound represented by the general formula (41) and a compound represented by the general formula (42) as in the reaction step 17-1. Can be produced by reacting in the presence of a base.

  Examples of the base used in the reaction step 17-1 include bases such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, and pyridine. It is done. Preferred is triethylamine.

  Examples of the solvent used in the reaction step 17-1 include ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; dichloromethane, chloroform, 1,2-dichloroethane, and the like. Halogenated hydrocarbons; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, cycloheptane, or a mixed solvent thereof. Preferred is dichloromethane.

  The production intermediate represented by the general formula (44) is obtained by reacting the compound (43) obtained in the reaction step 17-1 with chlorosulfonic acid as in the reaction step 17-2. Can be manufactured. In addition, the production intermediate represented by the general formula (44) is obtained by reacting the compound (43) obtained in the reaction step 17-1 with fuming sulfuric acid, followed by dipentapentoxide in the presence of a base. It can be produced by reacting with phosphorus.

  Examples of the base used in the reaction step 17-2 include bases such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, and pyridine. It is done. Preferred is potassium carbonate.

  The production intermediate represented by the general formula (45) includes the compound (44) obtained by the reaction step 17-2, a metal and an acid, lithium aluminum hydride, as in the reaction step 17-3. Alternatively, it can be produced by reduction using red phosphorus, iodine and an acid.

  Examples of the metal used in the reaction step 17-3 include metals such as zinc, tin, iron, and nickel. Zinc and tin are preferable.

  Examples of the acid used in the reaction step 17-3 include acids such as hydrochloric acid, sulfuric acid, and acetic acid. Preferred are hydrochloric acid, acetic acid and the like.

  The production intermediate represented by the general formula (46) is hydrolyzed using the compound (45) obtained in the reaction step 17-3 and an acid or a base, as in the reaction step 17-4. Can be manufactured.

  Examples of the acid used in the reaction step 17-4 include acids such as hydrochloric acid, sulfuric acid, and acetic acid. Preferred are hydrochloric acid, acetic acid and the like.

  Examples of the base used in the reaction step 17-4 include bases such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, triethylamine, diisopropylethylamine, and pyridine. Sodium hydroxide, potassium hydroxide and the like are preferable.

  The production intermediate represented by the general formula (27) includes the production intermediate (46) obtained by the reaction step 17-4 and the general formula (47) as in the reaction step 17-5. Can be produced by reacting in the presence or absence of a base and in the presence or absence of Rongalite (Rongalite, trade name of BASF; sodium hydroxymethanesulfinate dihydrate).

  The raw material represented by the general formula (47) is a known compound, and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Alternatively, it can be produced from a commercially available reagent according to a known method described in Experimental Chemistry Course, Organic Synthesis, etc.

  Examples of the base used in the reaction step 17-5 include bases such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, and pyridine. It is done. Preferred is potassium carbonate.

  Examples of the solvent used in the reaction step 17-5 include ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N , N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane and other aprotic polar solvents; Dichloromethane, chloroform, 1,2-dichloroethane and other halogenated hydrocarbons; Pentane, hexane, cyclohexane, cyclo Aliphatic hydrocarbons such as heptane or a mixed solvent thereof. N, N-dimethylformamide and the like are preferable.

  In any of the above reactions, the target compound can be obtained by performing ordinary operations in organic synthesis such as extraction, drying, concentration, and purification after the reaction is completed.

  Moreover, the structure of the target compound can be identified by a known analysis means such as an NMR spectrum.

  In addition, the substituted phenyl piperazine compound concerning this invention is not limited to the said manufacturing method, It can manufacture by arbitrary organic synthesis methods.

  The composition of the agricultural and horticultural pest control agent containing the compound according to the present invention as an active ingredient is a normal agricultural and horticultural pest except that the active ingredient contains the compound represented by the general formula (1) or a salt thereof. It is good also as a composition of a control agent. The normal composition is described in, for example, an agrochemical formulation guide (edited by: Japanese Society for Agricultural Chemicals Application Law, published by Japan Society for Plant Protection). That is, an appropriate carrier, auxiliary agent, surfactant, binder, stabilizer and the like may be added to the compound represented by the general formula (1).

  The composition of the agricultural and horticultural pesticide containing the compound according to the present invention can be formulated into any dosage form generally used as a dosage form for agricultural chemicals. For example, powder, coarse powder, DL (driftless) powder, flow dust, fine granules, fine granules, granules, wettable powder, wettable powder, liquid, sol (flowable), emulsion, and oil However, it is not limited to these.

  The content of the compound according to the present invention can be appropriately selected depending on the dosage form of the preparation and the method of use. In general, the preferred content is in the range of 0.1% to 90% by weight relative to the total amount of the formulation.

  When used as an agrochemical, the compound according to the present invention is a fungicide (for example, fungicides, bactericides, antiviral agents, plant resistance inducers), insecticides at the time of preparation or spraying as necessary. , An acaricide, nematocide, herbicide, avian repellent, growth regulator, fertilizer, soil improver, and the like, and may be mixed and applied.

  Of the above optional components, typical examples of the bactericides and insecticides are shown below, but are not limited thereto. For example, examples of the bactericidal agent include the following bactericidal agents.

(1) Copper agent Examples of the copper agent include basic copper chloride, basic sulfur copper, copper hydroxide, copper sulfate, and oxine copper. copper), nonylphenol sulfone copper, DBEDC, and the like.

(2) Inorganic disinfectant Examples of inorganic disinfectants include sulfur, lime-sulfur compound, sodium hydrogen carbonate, potassium hydrogen carbonate, metallic silver, and the like. Is mentioned.

(3) Organic sulfur fungicide Organic sulfur fungicides include ziram, manneb, mancozeb, ambam, polycarbamate, propineb, thiuram, Examples thereof include thiadiazin and zineb.

(4) Organophosphorus fungicides Examples of organophosphorus fungicides include IBP, EDDP, tolcrofos-methyl, pyrazophos, and fosetyl-alminium.

(5) Benzimidazole fungicide Examples of the benzimidazole fungicide include carbendazim, thiabendazole, thiophanate-methyl, and benomyl.

(6) Dicarboximide fungicide Examples of the dicarboximide fungicide include iprodione, procymidone, vinclozolin and the like.

(7) Carboxamide fungicides Carboxamide fungicides include oxycarboxin, carboxin, mepronil, flutolanil, boscalid, fluopyrampy, flapyrampy ), Thifluzamide, penthiopyrad, penflufen, penflufen, floxapyroxad, isopyrazane, and tolfenpyrad.

(8) Phenylamide fungicide As the phenylamide fungicide, metalaxyl (metalaxyl), metalaxyl M (metalaxyl-M), oxadixyl (furalaxyl), furaxyl (ofuraceyl), benalaxyl (b) M (benaxyl-M) and the like.

(9) Carboxylic acid amide fungicides As carboxylic acid amide fungicides, dimethomorph, flumorph, iprovalicalb, benchavaricarb-isopropyl, mandipropamide, and mandipropamide Examples include phenate.

(10) SBI Agents SBI agents include triflumizole, prochloraz, oxpoconazole fumarate, triadimuton, and bitterolil. Buconazole, hexaconazole, tebuconazole, propiconazole, prothioconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole Imibenconazole, cyproconazole, tetraconazole, simeconazole, metconazole, epoxiconazole, epoxiconazole, epoxiconazole, epoxiconazole, epoxiconazole, epoxiconazole, epoxiconazole, epoxiconazole, epoxiconazole, epoxiconazole, epoxiconazole. ), Triforine, triadimenol, flutriafol, pyrifenox, tridemorph, dodemorph, fenpropimorph, fenpropimorph N-propidin, spiroxamine, pyrisoxazole, fenhexamid, pyributicalcarb and the like.

(11) Strobilurin fungicides As strobilurin fungicides, there are azoxystrobin, cresoxime-methyl, trifloxystrobin, methinostrobin, oryastrobro Examples include pyraclostrobin, enestroburin, dimoxystrobin, picoxystrobin, pyribencarb, and fluoxastrobin.

(12) Anilinopyrimidine fungicides Examples of the anilinopyrimidine fungicides include cyprodinil, mepanipyrim, pyrimethanil and the like.

(13) Phenylpyrrole fungicide Examples of the phenylpyrrole fungicide include fludioxonil and fenpiclonil.

(14) Antibacterial fungicide Antibacterial fungicide includes kasugamycin, polyoxin, validamycin, streptomycin, oxytetracycline, and blasticidin S (b). Is mentioned.

(15) Other fungicides Other fungicides include DKF-1001 (code number), IKF-5411 (code number), MIF-1002 (code number), NC-233 (code number), S-2200 ( Code number), SB-4303 (code number), acibenzolar-S-methyl, amisulbrom, amethoctrazine, isothianil, isoprothioilanine, iminothine tris (albesilate)), iminoctadine triacetate, echromezol , Ethaboxam, oxolinic acid, captaphor, carpropamide, quinoxyphen, chloromethine, chloro, captan (ro), captanol cyazofamid), diethofencarb, diclocymet, diclomezine, dithianon, cyflufenamid, diflumetoxime, diflumetrim (Cymoxanil), sylthiofam, zoxamide, dazomet, thiadinyl, teclophthalam, tebufloquin, trizodol, trizofol (Tonnifanide), hydroxyisoxazole, pyriophenone, pyroquilon, fenoxanil, ferrimzone, fenpyrazamine, minpyrazamine (Phthalide), bupirimate, famoxadone, fenamidone, fluazinam, fluopialide, flusulfide, flusulfide, flusulfamide, flusulfide, flusulfide Hydrochloride, propenazole, pencyclon, holpet, methasulfocarb, metrafenone, lamina Emissions (laminarin), and the like.

  Examples of the insecticide include the following insecticides.

(1) Organophosphorus insecticides Organophosphorus insecticides include acephate, azinephos-methyl, chlorfenvinphos, chlorpyrifos, and chlorpyrifos-methyl. ), Cyanophos, diazinon, diclofenthion, dichlorvos, dimethoate, dimethylvinphos, disulfoton, EPN, etpro , Fe Namifos, fenitrothion, fenthion, isofenphos, isoxathion, malathion, methidathion, mevinphos, mevinfos, mevinphos Oxydemeton-methyl, parathion, parathion-methyl, phentoate, folate, fosalone, phosmet, phosphami Phosphomidon, Phoxim, Pirimiphos-methyl, Profenofos, Prophosfos, Prothiofos, Pyraclofos, Pyraclofos, Pyrafofos ), Temefos, terbufos, tetrachlorvinphos, thiomethon, trichlorfon, bamidithione and the like.

(2) Carbamate insecticides Carbamate insecticides include aldicarb, alaniccarb, bendiocarb, benfurcarb, carbaryl, carbofuran, carbofuran, carbofuran, carbofuran, carbofuran , Etiofencarb, fenobucarb, phenoxycarb, furathiocarb, isoprocarb, methoxicarb, methiocarb, methocarb , Pirimicarb, propoxur, thiodicarb, triazamate, XMC, xylylcarb and the like.

(3) Pyrethroid insecticides Pyrethroid insecticides include acrinathrin, allethrin, bifenthrin, cycloprotorin, cyfluthrin, beta-cyfluthrin, and beta-cyfluthrin Cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin (alpha-cypermethrin), alpha-cypermethrin (alpha-cypermethrin) ( deltamethrin, esfenvalerate, etofenprox, fenpropatorin, fenvalerate, flucitrate, fluvalinate, tuvulanate fluvalinate, halfenprox, methfluthrin, permethrin, phenothrin [(1R) -trans-isomer], pyrethrin (pyretrins), resmethrin s, resmethrin afluofen), tefluthrin (tefluthrin), tetramethrin (tetramethrin), and the like tralomethrin (tralomethrin).

(4) Nereistoxin Insecticide Examples of nereistoxin insecticides include bensultap, cartap hydrochloride, thiocyclam and the like.

(5) Neonicotinoid insecticides Examples of neonicotinoid insecticides include acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyramid, and nitenpyramid. thiamethoxam) and the like.

(6) Diamide Insecticide Examples of the diamide insecticide include chlorantaniprole, cyantraniprole, and fulbendamide.

(7) Phenylpyrazole insecticides Phenylpyrazole insecticides include acetoprole, etiprole, fipronil, flifiprole, pyrafluprole, pyriprole (pyriprole). Etc.

(8) Macrolide insecticides Macrolide insecticides include abamectin, avermectin, emamectin benzoate, lepimectin, milbemectin, spinate lam, spinate lam, spinate ram spinosad) and the like.

(9) Benzoylurea Insecticides As benzoylurea insecticides, bistrifluron, chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flucycloxuron, flucycloxuron Examples include phenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.

(10) Diacylhydrazine Insecticides Examples of diacylhydrazine insecticides include chromafenozide, halofenozide, methoxyphenozide, and tebufenozide.

(11) Other Insecticide Active Ingredients Other active insecticide active ingredients include azadirachtin, buprofezin, quinomethionate, chlorfenapyr, cyromodifenine, and cyromandihine. , Dicofol, dienochlor, endosulfan, flupiradifurone, flometoquin, flonicamid, fluphenirimur, flufenirimur Nonhydrol, hydroprene, indoxacarb, metaflumizone, metadehyde, metopryl, methyroxyl, methyroxyl (Pyrifluquinazone), pyriproxyfen, rotenone, spirotetramat, sulfoxafluor, tolfenpyrad, tolfenpyrad, soil oleate, oleoic acid, sodium oleate Acid glyceride, starch (starch), rapeseed, adhesive (Polybutene), propylene glycol mono fatty acid esters, machine oil (petroleum oil), nicotine sulfate (nicotine-sulfate), and the like phosphate ferric.

(12) Acaricides As miticides, there are acequinocyl, amidoflumet, amitraz, bifenazate, bromopropylate, clofentezine, clofentezin , Cyflumetofen, cyhexatin, ethoxazole, phenazaquin, fenbutatin oxide, fenopiocarb, fenpirocarb crypyrim, hexythiazox, propargite, pyrimidifene, pyridabenet, spirodiclofen, spiromesifene, spirometifen ) And the like.

(13) Nematicides As nematicides, there are aldoxycarb, cadusafos, carbam sodium, 1,3-dichloropropene, DCIP Fluensulfone, fosthiazate, imicyafos, levamisole hydrochloride, mesulfenate, methyl isothiocyanate, methyl isothiocyanate, methyl isothiocyanate Can be mentioned.

(14) Others Others include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrovirus (CPV), insect pox virus (Vx) ), Live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof, as insecticides and nematicides such as Steinerne carpocapsae and Pasteuria penetrans Examples include microbial pesticides, insect pheromones, and insect attractants.

  The agricultural and horticultural pesticides (for example, fungicides and insecticides) containing the compound according to the present invention as an active ingredient can be used in the same manner as in general methods. Specifically, in the case of wettable powders, liquids, emulsions, sols (flowables), granular wettable powders, or oils, the active ingredients are generally 1 ppm to 10000 ppm diluted with water 50 times to 10000 times. This dilute solution varies depending on the form of crops such as paddy rice and fruit trees, but it is 50L to 1000L, usually 100L to 600L. Can be sprayed on the foliage.

  For liquids, emulsions, or sols (e.g. flowables), do not dilute with water or within 50-fold, mainly in the amount of 5 mL to 5000 mL per 10 are as a microdispersion. It can be sprayed in the air. Air spraying is performed using a helicopter.

  In the case of powder, coarse granule, DL powder, flow dust agent, fine granule, fine granule, or granule, 0.3 kg to 5 kg of agent (active ingredient content is about 5 g to 500 g) per 10 ares, It may be applied to the foliage, soil surface, soil, or water surface at the plant pest occurrence site.

  In seedling box cultivation such as paddy rice, 10g to 100g per seedling box (standard size: 30cm x 60cm x 5cm) for granules, etc. It can be applied to the soil surface before or after sowing or during the seedling raising period.

  Specific examples of the pests that can be controlled using the substituted phenylpiperazine compounds according to the present invention include the following insects, mites, crustaceans, molluscs, and nematodes in agricultural and horticultural settings. However, it is not limited only to these.

  Furthermore, pests that can be controlled using the substituted phenylpiperazine compounds according to the present invention include the field of livestock disease treatment and livestock industry, and vertebrates such as humans, cattle, sheep, goats, pigs, poultry, Specific examples include parasites that parasitize inside or outside dogs, cats, fish, and the like. However, it is not limited only to these.

  For example, pests include the following insects.

  Examples of the stain include Yamato-shim (Ctenolepisma villosa), Shisami-sama (Lepisma saccharina), and Spotted scab (Thermobia domestica).

  Cockroaches include the cockroach (Periplaneta americana), the black cockroach (Periplaneta fuliginosa), the cockroach (Periplaneta japonica), and the German cockroach (Blatella germant).

  Examples of the termites include the American ant termites (Incitermes minor), the termites (Copttermes formosanus), the termites termites (Reticulitermes supertus), and the termites termites (Odontotermes formosanus).

  Examples of the locust include Rusporia lineosa, Teleoglyllus emma, Kelly (Gryllotalpa orientalis), Tosamabata (Locusta migratoria), and Obanei.

  Examples of the scallops include Trochaum pulsatorium, Hiratachate (Liposcelis bostrychofila), Uspo scallop (Liposcelis corrodens) and the like.

  Examples include the dipterous cape lice (Lipeureus caponis), the chick wolf shark (Menacanthus stramineus), the bull lice (Damalinia bovis), and the horse lice (Damalinia caprae).

  Examples of the louse include cattle lice (Haematopinus eurosternus), pig lice (Haematopinus suis), louse lice (Pediculus humanus capitis), head lice (Pediculus humus hus), and the like.

  The Thysanoptera, Hirazuhanaazamiuma (Frankliniella intonsa), western flower thrips (Frankliniella occidentalis), Croton thrips (Heliothrips haemorrhoidalis), soybean thrips (Mycterothrips glycines), yellow tea thrips (Scirtothrips dorsalis), rice thrips (Stenchaetothrips biformis), Minamikiiro Thrips palmi, Thrips tabaci, Hemithrips aculetus, Ponticultrips d ospyrosi) and the like.

  The Hemiptera, lid ten leafhopper (Arboridia apicalis), tea Roh green leafhopper (Empoasca onukii), green rice leafhopper (Nephotettix cincticeps), small brown planthopper (Laodelphax striatella), brown planthopper (Nilaparvata lugens), Sejirounka (Sogatella furcifera), Aobahagoromo (Geisha distintissima), citrus leafworm (Diaphorina citri), grape aphid (Viteus vitifoliae), pea aphid (Acyrthosiphon pisum), bean aphid (Aphis craccivora) , Cotton aphids (Aphis gossypii), apple aphids (Aphis spiraecoli), potato beetles erysimi), peaches aphid (Myzus persicae), barley beetle (Rhopalosiphum padi), barley beetle (Schizaphis graminum), schizophis piramica aphidula teratropia rantii), mandarin orange black aphid (Toxoptera citricida), mandarin orange spiny whitefly (Aleurocanthus spiniferus), silverleaf whitefly (Bemisia argentifolii), tobacco whitefly (Bemisia tabaci), mandarin orange whitefly (Dialeurodes citri), greenhouse whitefly (Trialeurodes vaporariorum), giant straw sandals scale insects (Drosichia corporatea), Icerya purchasi, Prunococcus citri, Planococcus kraunhiae, stag beetle Musi (Pseudococcus comstocki), Tsunoroumushi (Ceroplastes ceriferus), Rubiroumushi (Ceroplastes rubens), Acamar scale insects (Aonidiella aurantii), no circle scale insects (Diaspidiotus perniciosus), white peach scale (Pseudaulacaspis pentagona), Yano yanonensis (Unaspis yanonensis), Red Star Stink bugs (Creontides colorips), Trichotylus caestierium, Stephanitis nashii, Stephigumbai (Steph) nitis pyrioides), thorns Shirahoshi bug (Eysarcoris aeneus), giant thorns Shirahoshi bug (Eysarcoris lewisi), Tsuyaaokamemushi (Glaucias subpunctatus), red streaks stink bugs (Graphosoma rubrolineatum), brown marmorated stink bug (Halyomorpha halys), order Hemiptera (Nezara antennata), Southern blue stink bug (Nezara viridula), Chinese red stink bug (Plautia rossota stali), Japanese cabbage leaf bug (Caverelius saccharivorus), Japanese red headed bug (Tomogo moth) Reptoridae (Leptocorisa chinensis), Hoso-heli beetle (Riptortus clavatus), Hoso-hari-chome (Cretus puntiger), Red-eared beetle (Rhopalus maculatus), Citrus lice, etc.

  The Coleoptera, Aodougane (Anomala albopilosa), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), flower chafer (Eucetonia pilifera), core Oh flower chafer (Gametis jucunda), Nagachakogane (Heptophylla picea), Japanese beetle (Popillia japonica), Tobii Romna boso rice (Agriotes ogurae fuscicollis), Kabayo kometsuki (Ectinus sericeus sericeus), Marubitus fornumi forthum, reme marus v. sci), cigarette beetle (Lasioderma serricorne), red flour (Tenebroides mauritanicus), Hime Hirata Keshikisui (Epuraea domina), bean beetle (Epilachna varivestis), the beetle, Epilachna vigintioctopunctata (Henosepilachna vigintioctopunctata), Chai Loco Meno mealworm (Tenebrio molitor), red flour Japanese tiger beetle (Tribolium castaneum), Japanese beetle beetle (Anoplophora malasiaca), Japanese pine beetle (Monochumus alternatus endai), Grape tiger beetle (Xylotrechus pyrrhr) oderus), adzuki bean weevil (Callosobruchus chinensis), cucurbit leaf beetle (Aulacophora femoralis), Kamenokohamushi (Cassida nebulosa), Ten site bi potato beetle (Chaetocnema concinna), Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi) , Diabrotica spp., Colorado potato beetle (Leptinotarsa decemlineata), Rice beetle (Oulema oryzae), Phyllotreta striolat ), Sweet potato weevil (Cylas formicarius), boll weevil (Anthonomus grandis), Imozoumushi (Euscepes postfasciatus), alfalfa weevil (Hypera postica), vegetable weevil (Listroderes costirostris), rice weevil (Echinocnemus bipunctatus), rice water weevil (Lissorhoptrus oryzophilus), Blossom weevil (Sitophilus zeamais), Shibao weevil (Sphenophrus venatus vestitus), pine beetle (Tomicus piniperda), hirata kumuushi (Lyctus brus) neus), and the like.

  Fleas include fleas (Ceraphyllus gallinae), dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis), chicken fleas (Echidophaga galis), fleas (exotica gall)

  The Diptera, soybean pod gall midge (Asphondylia yushimai), Aedes aegypti (Aedes aegypti), Anopheles sinensis (Anopheles sinensis), mosquito (Culex pipines pallens), Culex quinquefasciatus (Culex quinquefasciatus), Culex (Culex tritaeniorhynchus), melon fly (Bactrocera cucurbitae), Bactrocera Dorsalis, Agromyza oryzae, Namoguri flies (Chromatomyia horticola), Lorimyza huidobrensis, Doo leafminer (Liriomyza sativae), legume leafminer (Liriomyza trifolii), onion maggot (Delia antiqua), seedcorn maggot (Delia platura), housefly (Musca domestica), stable fly (Stomoxys calcitrans), and the like.

  As for the Lepidoptera, Adoxophyces honmai, Adokophyes orana phasiata, Arhips fuscocupreus, Argyps fuscocupreus, Codylinga , Legumnivora glycinivolorella, Pandemis heparana, tinea translucens, peach leaf moth (Lyonetia clarkella), lynmon leaf moth inella), Chanohosoga (Caloptilia theivora), the apple leaf miner (Phyllonorycter ringoniella), mandarin orange leafminer (Phyllocnistis citrella), diamondback moth (Plutella xylostella), grapes Sukashiba (Nokona regalis), Kosukashiba (Synanthedon hector), Kakinohetamushiga (Stathmopoda masinissa), Imokibaga (Helcystogramma triannullum), cotton beetle (Pectinophora gossypiella), peach sink moth (Carposina sasakii), green moth (Chilo suppressalis), ko Nomeiga (Cnaphalocrocis medinalis), peach Nogo moth (Conogethes punctiferalis), high Madara Roh moth (Hellula undalis), the European corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), white-position character moth (Etiella zinckenella), swallowtail (Papilio xuthus ), White butterfly (Pieris rapae crucivora), Imonmonse seri (Parnara guttata guttata), Artemisia dwarf (Ascotis selenaria), Chadokuga (Ana pseudoconspermais) (Lymantria dispar), the United States white Arctiidae (Hyphantria cunea), black cutworm (Agrotis ipsilon), Kaburayaga (Agrotis segetum), Tamanagin'uwaba (Autographa nigrisigna), cotton bollworm (Helicoverpa armigera), Heliothis (Heliothis spp. ), Miostra brassicae, Mythymna separata, Naranga aenescens, Spodoptera exigua, and spodopter ur.

  The Hymenoptera, Chu range sawfly (Arge pagana), Kaburahabachi (Athalia rosae ruficornis), Kuritamabachi (Dryocosmus kuriphilus), Kiirosuzumebachi (Vespa simillima xanthoptera), Formica japonica (Formica japonica), Iehimeari (Monomorium pharaonis), fire ant (Solenopsis invicta ) And the like.

  The mites, bees Hegi Ita mite (Varroa jacobsoni), chicken mites (Dermanyssus gallinae), house dust mite (Ornithonyssus bacoti), Torisashidani (Ornithonyssus sylvialum), Ooyamadani (Amblyomma spp.), Boophilus microplus (Boophilus microplus), Amimemadani (Dermacentor spp. ), Tick ticks (Haemaphysalis flava), winged tick ticks () Haemophysalis campanulata, Haephaphysalis longicornis (Ixodes oodus tick) rsulcatus), Rhipicephalus sanguineus (Rhipicephalus sanguineus), Hakusaidani (Penthaleus erythrocephalus), Mugidani (Penthaleus major), cyclamen dust mites (Phytonemus pallidus), Chanohokoridani (Polyphagotarsonemus latus), streak-but-dust mites (Tarsonemus bilobatus), Inunikibidani (Demodex canis) , Catfish mites (Demodex cati), rice spider mites (Oligonychus shinkajii), citrus mite mites (Pananychus citri), blue mite spider mites (Pananychus mori), apple spider mites Panonychus ulmi), carmine spider mite (Tetranychus cinnabarinus), kanzawai (Tetranychus kanzawai), two-spotted spider mite (Tetranychus urticae), tea Roh Naga rust mite (Acaphylla theavagrans), Tulip rust mite (Aceria tulipae), tomato rust mite (Aculops lycopersici), mandarin orange rust mite (Aculops pelekassi ), Apple rust mites (Aculus schlettendali), tea rust mites (Calacarus carinatus), pear rust mites (Epitrimerus pyri), green rust mites (Eriophytes chibaens) s), citrus last mite (Phyllocoptruta oleivora), the bulb mite, Rhizoglyphus (Rhizoglyphus robini), Tyrophagus (Tyrophagus putrescentiae), spinach Kenna mites (Tyrophagus similis), chicken mites (Knemidokoptes spp. ), Sheep 9,000 mites (Psoroptes ovis), cat foraminous mites (Notoedres cati), SENKOU mites (Sarcoptes scabiei), red mites (Leptotrombidium akamushi), Nekotsumedani (Cheyletiella blakei), Inutsumedani (Cheyletiella yasguri), farinae (Dermatophagoides farinae) , Latrodetectus hasseltii and the like.

  Examples of the crustacean include Oxidus gracilis.

  Examples of the isopod include armadillium vulgare.

  Examples of the decapod include the American crayfish (Procambarus clarkii).

  Examples of the order of the dipteran are Boletelliella hortensis.

  Examples of the mollusc include Pomacea canalicula and the like.

  Examples of the pulmonary eye include African maimai (Achatina falica), slug (Meghiatum bilineatum), Chaukoura slug (Lehmannina valentiana), and Uskawa maimai (Acusta despecta sieboldian).

  Nematodes include strawberry nematodes (Notothylenchus acris), sweet potato root nematodes (Meloidogyne incognita), potato cyst nematodes (Globodera rostemisen), soybean cyst nematodes (Heterocernes) Pratylenchus coffea, Pratylenchus penetran, Nepalese nematode (Pratylenchus yamagutii), Nepheline nematode (Aphelenchus avenae) Nematode (Aphelenchoides besseyi), pine wood nematode (Bursaphelenchus xylophilus), and the like.

  Other animal internal parasites include roundworms, worms, etc., filariae, liver dystomia, lung dystoma, Yokokawa flukes, Schistosoma japonicum, striped worms, striped worms, echinococcus Examples include headworms.

  Hereinafter, the present invention will be described more specifically based on synthesis examples of substituted phenylpiperazine compounds, formulation examples, and evaluation of control effects against pests, but the present invention is not limited thereto.

1. Synthesis Example of Substituted Phenylpiperazine Compound <Example 1>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (4-chlorobenzyl) piperazine (1-695)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (4-chlorobenzyl) piperazine-4-oxide (200 mg, 0.430 mmol) in tetrahydrofuran To the solution (2 ml), copper iodide (82 mg, 0.431 mmol) and N, N-diisopropylethylamine (56 mg, 0.433 mmol) were added at room temperature, and the mixture was heated to reflux for 3 hours. The precipitate was filtered off, water was added to the filtrate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/1) to give the title compound as a brown oil (yield 95 mg, 49%).

<Example 2>
<1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-[{4-[(5-trifluoromethyl) -2-pyridyloxy] phenyl } Methyl] piperazine-4-oxide (1-798) and 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4-[{4-[( Synthesis of 5-trifluoromethyl) -2-pyridyloxy] phenyl} methyl] piperazine-4-oxide (1-799)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-[{4-[(5-trifluoromethyl) -2-pyridyloxy] phenyl} Methyl] piperazine (170 mg, 0.304 mmol) in dichloromethane (2 ml) was added 70% 3-chloroperbenzoic acid (75.0 mg, 0.304 mmol) at 0 ° C. and stirred at the same temperature for 1 hour. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: methanol / chloroform = 1/5) to give 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethyl) as white crystals. Thio) phenyl] -4-[{4-[(5-trifluoromethyl) -2-pyridyloxy] phenyl} methyl] piperazine-4-oxide (56 mg, 32% yield) and 1- [ 2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4-[{4-[(5-trifluoromethyl) -2-pyridyloxy] phenyl} methyl] piperazine -4-oxide (yield 41 mg, yield 23%) was obtained.

The following compounds were synthesized according to the method of Example 2.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-chlorobenzyl) piperazine-4-oxide (1-694), 1- [ 2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (4-chlorobenzyl) piperazine-4-oxide (1-696)

<Example 3>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (trifluoromethylsulfonyl) piperazine (1-667)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (trifluoromethylsulfonyl) piperazine (210 mg, 0.477 mmol) in chloroform (4 ml) 70% 3-chloroperbenzoic acid (118 mg, 0.477 mmol) was added at room temperature and stirred at the same temperature for 9 hours. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/9) to give the title compound as white crystals (yield 170 mg, 80%).

The following compound was synthesized according to the method of Example 3.
t-butyl 4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] piperazine-1-carboxylate (1-601), 1- [2-fluoro-4 -Methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (4-chlorobenzoyl) piperazine (1-908), 1- [2-fluoro-4-methyl-5- (2 , 2,2-trifluoroethylsulfinyl) phenyl] -4- (4-chlorobenzenesulfonyl) piperazine (1-1128), N- [2-methyl-4- {1,2,2,2-tetrafluoro-1 -(Trifluoromethyl) ethyl} phenyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] piperazine-1- Carboxamide (1-1098), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (acetyl) piperazine (1-369), 1- [ 2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (4-chlorophenylacetyl) piperazine (1-550), 1-methyl-5- (2,2 , 2-trifluoroethylsulfinyl) phenyl] -4- (trifluoromethylsulfonyl) piperazine (1-218), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) ) Phenyl] -4- (N-ethylcarbamoyl) piperazine (1-611), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoro) Roethylsulfinyl) phenyl] -4- (N-isopropylcarbamoyl) piperazine (1-614), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl]- 4- (difluoromethylsulfonyl) piperazine (1-664), 1- (pivaloyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] piperazine (1 -404), 1- (cyclohexanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] piperazine (1-419), 1- (3 3,3-trifluoro-2,2-dimethylpropanoyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoro) Ethylsulfinyl) phenyl] piperazine (1-537), 1- (2,2-difluoro-1-methyl-cyclopropanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2- Trifluoroethylsulfinyl) phenyl] piperazine (1-437), 1- [2,2-dichloro-1- (4-chlorophenyl) cyclopropanecarbonyl] -4- [2-fluoro-4-methyl-5- (2 , 2,2-trifluoroethylsulfinyl) phenyl] piperazine (1-486), 1- [2-fluoro-4-methyl-5- (3,3,3-trifluoropropylsulfinyl) phenyl] -4- ( Trifluoromethylsulfonyl) piperazine (2-368), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfuryl) Finyl) phenyl] -4- (N, N-dimethylcarbamoyl) piperazine (1-621), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl]- 4- (N-methylcarbamoyl) piperazine (1-609), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4-carbamoylpiperazine (1- 607), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (2-ethylbutanoyl) piperazine (1-388), 1- [ 2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (2-propylpentanoyl) piperazine (1-390 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (3,3-dimethylbutanoyl) piperazine (1-392), 1- [ 2,2-difluoro-1- (trifluoromethyl) cyclopropanecarbonyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] piperazine (1-450 ), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (3,3-difluorocyclopentanecarbonyl) piperazine (1-501)

<Example 4>
<1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfonyl) phenyl] -4- (trifluoromethylsulfonyl) piperazine (1-669), 1- [2-fluoro -4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (trifluoromethylsulfonyl) piperazine (1-667) and 1- [2-fluoro-4-methyl-5 Synthesis of (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (trifluoromethylsulfonyl) piperazine-1-oxide (1-668)
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (trifluoromethylsulfonyl) piperazine (320 mg, 0.727 mmol) in dichloromethane (5 ml) 70% 3-chloroperbenzoic acid (394 mg, 1.60 mmol) was added at 0 ° C. and stirred at the same temperature for 1 hour. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (elution solvent: ethyl acetate) to give white crystalline 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfonyl) phenyl]- 4- (trifluoromethylsulfonyl) piperazine (yield 11 mg, yield 3%), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl]- 4- (Trifluoromethylsulfonyl) piperazine (53 mg, 15% yield) and white amorphous 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (Trifluoromethylsulfonyl) piperazine-1-oxide (yield 260 mg, 55% yield) was obtained.

<Example 5>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (4-chlorobenzoyl) piperazine-1-oxide (1-909)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (4-chlorobenzoyl) piperazine (160 mg, 0.346 mmol) in dichloromethane (3 ml) 70% 3-chloroperbenzoic acid (85.0 mg, 0.344 mmol) was added at 0 ° C. and stirred at the same temperature for 1 hour. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: chloroform / methanol = 8/1) to give the title compound (yield 130 mg, 78%) as colorless candy.

The following compound was synthesized according to the method of Example 5.
1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (4-chlorobenzenesulfonyl) piperazine-1-oxide (1-1129), 1- [ 2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4- (4-chlorophenylacetyl) piperazine-1-oxide (1-551)

<Example 6>
<1- (2,2-Dichloro-1-methylcyclopropanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] piperazine (1-457 ) And 1- (2,2-dichloro-1-methylcyclopropanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] piperazine-4- Synthesis of Oxide (1-458)>
1- (2,2-Dichloro-1-methylcyclopropanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (340 mg, 0. 741 mmol) in chloroform (7 ml) was added 70% 3-chloroperbenzoic acid (220 mg, 0.963 mmol) at 0 ° C. and stirred at the same temperature for 1 hour. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: methanol / chloroform = 1/50) to give 1- (2,2-dichloro-1-methylcyclopropanecarbonyl) -4- [2-fluoro as a yellow oil. -4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] piperazine (yield 150 mg, 43% yield) and 1- (2,2-dichloro-1-methylcyclopropanecarbonyl) as white crystals ) -4- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] piperazine-4-oxide (yield 100 mg, 27% yield) was obtained.

The following compound was synthesized according to the method of Example 6.
1- (2-methylbutanoyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] piperazine (1-398), 1- (2-methyl Butanoyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] piperazine-4-oxide (1-399), 1- (1-methylcyclopropane) Carbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] piperazine (1-428), 1- (1-methylcyclopropanecarbonyl) -4- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] piperazine-4-oxide (1-429), 1- (1-ethyl- , 2-Difluorocyclopropanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] piperazine (1-443), 1- (1-ethyl- 2,2-Difluorocyclopropanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl] piperazine-4-oxide (1-444)

<Example 7>
<1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2-difluoro-1-methylcyclopropanecarbonyl) piperazine-1-oxide Synthesis of (1-459)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2-difluoro-1-methyl-cyclopropanethiocarbonyl) piperazine (600 mg, 1.36 mmol) in dichloromethane (10 ml) was added 70% 3-chloroperbenzoic acid (671 mg, 2.72 mmol) at 0 ° C. and stirred at the same temperature for 1 hour. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/2) to give the title compound (yield 286 mg, 48%) as a yellow oil.

<Example 8>
<Synthesis of 1- [2-chloro-6-fluoro-4-methyl-3- (2,2,2-trifluoroethylthio) phenyl] -4- (trifluoromethylsulfonyl) piperazine (1-76)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (trifluoromethylsulfonyl) piperazine (300 mg, 0.681 mol) in dichloromethane (3 ml) To the mixture was added sulfuryl chloride (92 mg, 0.682 mmol) at 0 ° C., and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/10) to give the title compound (yield 170 mg, 53%) as a yellow oil.

The following compound was synthesized according to the method of Example 8.
1- (4-Chlorobenzyl) -4- [2-chloro-6-fluoro-4-methyl-3- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-83)

<Example 9>
<Synthesis of 1- [2-bromo-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (trifluoromethylsulfonyl) piperazine (1-1314)>
1- [4-Methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (trifluoromethylsulfonyl) piperazine (400 mg, 0.947 mmol) in acetic acid solution (3 ml) with bromine (151 mg 0.945 mmol) at room temperature and stirred at the same temperature for 30 minutes. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with an aqueous sodium thiosulfate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound as white crystals (yield 110 mg, 25%).

<Example 10>
<Synthesis of 1- (4-chlorobenzenesulfonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-1127)>
A solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (100 mg, 0.324 mmol) and triethylamine (65.0 mg, 0.644 mmol) in dichloromethane ( 2-Chlorobenzenesulfonyl chloride (89.0 mg, 0.422 mmol) was added at 0 ° C., and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/4) to give the title compound (yield 110 mg, 70%) as white crystals.

The following compound was synthesized according to the method of Example 10.
1- (3-chlorobenzenesulfonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-11161), 1- (2-chlorobenzenesulfonyl) ) -4- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-1164), 1- (3,4-dichlorobenzenesulfonyl) -4- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-1167), 1- (4-t-butylbenzenesulfonyl) -4- [2-fluoro -4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-1138), 1- (4-methoxybenzenesulfonyl) -4- [2-fluoro 4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-1145), 1- (3-pyridylsulfonyl) -4- [2-fluoro-4-methyl-5- ( 2,2,2-trifluoroethylthio) phenyl] piperazine (1-1187), 1- (5-bromo-2-thienylsulfonyl) -4- [2-fluoro-4-methyl-5- (2,2 , 2-trifluoroethylthio) phenyl] piperazine (1-1197), 1- (2,4-dichlorobenzenesulfonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-tri Fluoroethylthio) phenyl] piperazine (1-1170), 1- (4-trifluorobenzenesulfonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) Phenyl] piperazine (1-1142), 1- (4-bromobenzenesulfonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1- 1131), 1- (4-chlorobenzenesulfonyl) -4- [2,4-dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-260), 1- (4-chlorobenzene) Sulfonyl) -4- [4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-223), 1- (4-chlorobenzenesulfonyl) -4- [2-fluoro-4 -Methyl-5- (cyclopropylmethylthio) phenyl] piperazine (2-248), 1- (4-chlorobenzenesulfonyl) -4- [2-fluoro-4-methyl -5- (2,2,2-trifluoroethylthio) phenyl] -2-methylpiperazine (3-58), 1- (4-chlorobenzenesulfonyl) -4- [2-fluoro-4-methyl-5 (Isobutylthio) phenyl] piperazine (2-72), 1- (4-chlorobenzenesulfonyl) -4- [2-fluoro-4-methyl-5- (pentafluoroethylthio) phenyl] piperazine (2-347)

<Example 11>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-methylpiperazine (1-284)>
Triethylamine (197 mg, 1.95 mmol) to a dichloromethane solution (2 ml) of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (200 mg, 0.650 mmol) And methyl iodide (92.2 mg, 0.65 mmol) were added at room temperature and stirred at the same temperature overnight. The reaction mixture was poured into water and extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: methanol / chloroform = 1/5) to give the title compound (yield 82.0 mg, yield 39%) as a yellow oil.

The following compound was synthesized according to the method of Example 11.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-n-butylpiperazine (1-288), 1-[(2-pyridyl) methyl] -4- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-876), 1-[(3-pyridyl) methyl] -4- [2 -Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-878), 1-[(4-pyridyl) methyl] -4- [2-fluoro-4- Methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-880)

<Example 12>
<Synthesis of 1- [2,4-difluoro5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-chlorobenzyl) piperazine (1-1343)>
To a dichloromethane solution (10 ml) of 1- [2,4-difluoro5- (2,2,2-trifluoroethylthio) phenyl] piperazine (300 mg, 0.96 mmol) was added 4-chlorobenzyl chloride (170 mg, 1. 06 mmol), triethylamine (190 mg, 1.92 mmol) were added at 0 ° C., and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/4) to give the title compound as a colorless oil (yield 340 mg, yield 81%).

The following compound was synthesized according to the method of Example 12.
1- [2-Fluoro-4-methyl-5- (isobutylthio) phenyl] -4- (4-chlorobenzyl) piperazine (2-66)

<Example 13>
<1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2,2-trifluoroethylsulfonyl) piperazine (1-670) Composition>
Triethylamine (197 mg, 1.95 mmol) in a dichloromethane solution (5 ml) of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (300 mg, 0.973 mmol) And 2,2,2-trifluoroethanesulfonyl chloride (266 mg, 1.45 mmol) were added at 0 ° C. and stirred at the same temperature for 1 hour. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound as white crystals (yield 274 mg, yield 62%).

The following compound was synthesized according to the method of Example 13.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (nonafluorobutylsulfonyl) piperazine (1-674), 1- [2-fluoro- 4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-methylsulfonylpiperazine (1-641), 1- (chloromethylsulfonyl) -4- [2-fluoro-4-methyl -5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-661), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl ] -4- (difluoromethylsulfonyl) piperazine (1-663), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (ethyl Sulfonyl) piperazine (1-653), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (isopropylsulfonyl) piperazine (1-657), 1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (cyclopropylsulfonyl) piperazine (1-644), 1- [2-fluoro-4 -Methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (cyclohexylsulfonyl) piperazine (1-652), 1- [2-fluoro-4-methyl-5- (2,2 , 2-trifluoroethylthio) phenyl] -4- (benzylsulfonyl) piperazine (1-675), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoro) Ethylthio) phenyl] -4- (4-chlorobenzyl) piperazin (1-676)

<Example 14>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-vinylsulfonylpiperazine (1-677)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1.0 g, 3.25 mmol) in dichloromethane (11 ml) in triethylamine (660 mg, 6. 49 mmol) and 2-chloroethanesulfonyl chloride (790 mg, 4.87 mmol) were added at 0 ° C., and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/8) to give the title compound as white crystals (yield 670 mg, 52%).

<Example 15>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (N, N-dimethylsulfamoyl) piperazine (1-683)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (200 mg, 0.649 mmol) in dichloromethane (3 ml) with triethylamine (131 mg, 1.30 mmol) And N, N-dimethylsulfonyl chloride (103 mg, 0.714 mmol) was added at 0 ° C. and stirred at room temperature for 4 hours. The reaction mixture was poured into water and extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/4) to give the title compound as white crystals (yield 140 mg, yield 52%).

<Example 16>
<Synthesis of 4-chlorophenyl 4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine-1-carboxylate (1-1058)>
Triethylamine (197 mg, 1.95 mmol) in dichloromethane solution (3 ml) of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (300 mg, 0.973 mmol) And 4-chlorophenyl chloroformate (204 mg, 1.07 mmol) was added at 0 ° C. and stirred at room temperature for 4 hours. The reaction mixture was poured into water and extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to obtain the title compound as a yellow oil (yield 325 mg, yield 72%).

<Example 17>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (N, N-dimethylcarbamoyl) piperazine (1-620)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (308 mg, 1.0 mmol) and triethylamine (202 mg, 2.0 mmol) in dichloromethane (5 ml) To the solution, dimethylcarbamoyl chloride (108 mg, 1.0 mmol) was added at 0 ° C., and the mixture was stirred at room temperature for 8 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / toluene = 1/5) to give the title compound as a pale yellow oil (yield 380 mg, yield 100%).

The following compound was synthesized according to the method of Example 17.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (N, N-dimethylthiocarbamoyl) piperazine (1-632)

<Example 18>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (acetyl) piperazine (1-368)>
Triethylamine (197 mg, 1.95 mmol) in dichloromethane solution (3 ml) of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (300 mg, 0.973 mmol) And acetyl chloride (84.0 mg, 1.07 mmol) were added at 0 ° C. and stirred at room temperature for 4 hours. The reaction mixture was poured into water and extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: methanol / chloroform = 1/99) to obtain the title compound as a pale yellow oil (yield 340 mg, yield 100%).

The following compound was synthesized according to the method of Example 18.
1- [4-Methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (acetyl) piperazine (1-207), 1-acetyl-4- [5-{(2,2 Dichloro-1-methylcyclopropyl) methylthio} -2-fluoro-4-methylphenyl] piperazine (2-254), 1-acetyl-4- [2-fluoro-4-methyl-5- (2,2,2) -Trifluoroethylthio) phenyl] -2-methylpiperazine (3-36), 1- [2,4-difluoro5- (2,2,2-trifluoroethylthio) phenyl] -4- (acetyl) piperazine (1-1332), 1- [2-Fluoro-4-methyl-5- (pentafluoroethylthio) phenyl] -4- (acetyl) piperazine (2-327)

<Example 19>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (pivaloyl) piperazine (1-403)>
Triethylamine (197 mg, 1.95 mmol) in dichloromethane solution (3 ml) of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (300 mg, 0.973 mmol) And pivaloyl chloride (129 mg, 1.07 mmol) were added at 0 ° C. and stirred at room temperature for 4 hours. The reaction mixture was poured into water and extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound as a yellow oil (yield 347 mg, 68%).

The following compound was synthesized according to the method of Example 19.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (propionyl) piperazine (1-373), 1- [2-fluoro-4-methyl -5- (2,2,2-trifluoroethylthio) phenyl] -4- (pentanoyl) piperazine (1-377), 1- [2-fluoro-4-methyl-5- (2,2,2- Trifluoroethylthio) phenyl] -4- (isobutanoyl) piperazine (1-393), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (Dichloroacetyl) piperazine (1-521), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (trichloroacetyl) piperazine (1-52 ), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (methoxyacetyl) piperazine (1-542), 1- [2-fluoro- 4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2-ethylbutanoyl) piperazine (1-387), 1- [2-fluoro-4-methyl-5 (2,2,2-trifluoroethylthio) phenyl] -4- (2-propylpentanoyl) piperazine (1-389), 1- [2-fluoro-4-methyl-5- (2,2,2 -Trifluoroethylthio) phenyl] -4- (3,3-dimethylbutanoyl) piperazine (1-391), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethyl) Thio) phenyl] -4- (3 Phenylpropanoyl) piperazine (1-567), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (1-adamantanecarbonyl) piperazine (1 −406)

<Example 20>
<1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2-dichloro-1-methylcyclopropanecarbonyl) piperazine (1-456 )
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (200 mg, 0.649 mmol) in dichloromethane (2 ml) with triethylamine (131 mg, 1.30 mmol) And 2,2-dichloro-1-methylcyclopropanecarbonyl chloride (158 mg, 0.847 mmol) were added at 0 ° C. and stirred at room temperature for 1 hour. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound as white crystals (yield 289 mg, 97%).

The following compound was synthesized according to the method of Example 20.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (cyclopropanecarbonyl) piperazine (1-407), 1- [2-fluoro-4 -Methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2-phenyl-1-cyclopropanecarbonyl) piperazine (1-431)

<Example 21>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-chlorobenzoyl) piperazine (1-907)>
A solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (100 mg, 0.324 mmol) and triethylamine (65.0 mg, 0.644 mmol) in dichloromethane ( 2-Chlorobenzoyl chloride (74.0 mg, 0.423 mmol) was added at 0 ° C. and stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound (yield 110 mg, 76%) as a yellow candy.

The following compound was synthesized according to the method of Example 21.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-tert-butylbenzoyl) piperazine (1-918), 1- [2- Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (3-chlorobenzoyl) piperazine (1-950), 1- [2-fluoro-4-methyl-5 -(2,2,2-trifluoroethylthio) phenyl] -4- (2-chlorobenzoyl) piperazine (1-956), 1- [2-fluoro-4-methyl-5- (2,2,2) -Trifluoroethylthio) phenyl] -4- (3,4-dichlorobenzoyl) piperazine (1-960), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) ) Phenyl] -4- (4- Toxibenzoyl) piperazine (1-925), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- [4- (trifluoromethyl) benzoyl] Piperazine (1-922), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (3-fluorobenzoyl) piperazine (1-948), 1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (3-bromobenzoyl) piperazine (1-952), 1- [2-fluoro- 4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (3-trifluoromethylbenzoyl) piperazine (1-989), 1- [2-fluoro-4-methyl 5- (2,2,2-trifluoroethylthio) phenyl] -4- (3-trifluoromethoxybenzoyl) piperazine (1-991), 1- [2-fluoro-4-methyl-5- (2, 2,2-trifluoroethylthio) phenyl] -4- (3-methylbenzoyl) piperazine (1-954), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethyl) Thio) phenyl] -4- (3-chloro-4-fluorobenzoyl) piperazine (1-967), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl ] -4- (3,4-difluorobenzoyl) piperazine (1-958), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- ( 3,5-di Chlorobenzoyl) piperazine (1-965), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (3,5-difluorobenzoyl) piperazine ( 1-964), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- [2- (trifluoromethyl) -3-pyridylcarbonyl] piperazine (1-1001), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (3-pyridylcarbonyl) piperazine (1-998), 1 -[2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (6-chloronicotinoyl) piperazine (1-1005), 1- [2,4- The Til-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-chlorobenzoyl) piperazine (1-256), 1- [4-methyl-5- (2,2,2- Trifluoroethylthio) phenyl] -4- (4-chlorobenzoyl) piperazine (1-222), 1- [2-fluoro-4-methyl-5- (cyclopropylmethylthio) phenyl] -4- (4-chloro Benzoyl) piperazine (2-246), 1- (4-chlorobenzoyl) -4- [5-{(2,2dichloro-1-methylcyclopropyl) methylthio} -2-fluoro-4-methylphenyl] piperazine ( 2-258), 1- [2,4-difluoro-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-chlorobenzoyl) piperazine (1-1347), 1 -[2-Fluoro-4-methyl-5- (isobutylthio) phenyl] -4- (4-chlorobenzoyl) piperazine (2-70), 1- [2-fluoro-4-methyl-5- (pentafluoro) Ethylthio) phenyl] -4- (4-chlorobenzoyl) piperazine (2-345)

<Example 22>
<Synthesis of 1- (4-chlorobenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-693)>
To a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (100 mg, 0.324 mmol) in N, N-dimethylformamide (1 ml) was added potassium carbonate (1 ml). 67.0 mg, 0.485 mmol) and 4-chlorobenzyl chloride (57.0 mg, 0.354 mmol) were added at room temperature and stirred at the same temperature for 3 hours. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound (yield 110 mg, 78%) as a yellow oil.

The following compound was synthesized according to the method of Example 22.
1- (4-Chlorobenzyl) -4- [2,4-dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-246), 1- (4-chlorobenzyl)- 4- [4-Methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-221), 1- (4-chlorobenzyl) -4- [2-fluoro-4-methyl- 5- (cyclopropylmethylthio) phenyl] piperazine (2-242), 1- (4-chlorobenzyl) -4- [2-fluoro-4-methyl-5- (4-chlorobenzylthio) phenyl] piperazine (2 -200), 1- (4-chlorobenzyl) -4- [5-{(2,2dichloro-1-methylcyclopropyl) methylthio} -2-fluoro-4-methylphenyl] -4- (trifluoromethyl The Phonyl) piperazine (2-257), 1- [2-fluoro-4-methyl-5- (3,3,3-trifluoropropylthio) phenyl] -4- (4-chlorobenzyl) piperazine (2-371) ), 1- (4-chlorobenzyl) -4- [2-fluoro-4-methyl-5- (pentafluoroethylthio) phenyl] piperazine (2-341)

<Example 23>
<1-[{4- (4-Chlorophenoxy) phenyl} methyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-770 )
To a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (108 mg, 0.350 mmol) in N, N-dimethylformamide (1 ml) was added potassium carbonate (1 ml). 73.0 mg, 0.528 mmol) and 1- (chloromethyl) -4- (4-chlorophenoxy) benzene (97.5 mg, 0.385 mmol) were added at room temperature and stirred at the same temperature for 2 hours. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound (yield 125 mg, yield 68%) as colorless candy.

The following compound was synthesized according to the method of Example 23.
1-[{4- (4-Chlorophenoxy) phenyl} methyl] -4- [2,4-dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-252)

<Example 24>
<1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-[{4-[(5-trifluoromethyl) -2-pyridyloxy] phenyl } Synthesis of methyl] piperazine (1-797)>
To a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (200 mg, 0.649 mmol) in N, N-dimethylformamide (2 ml) was added potassium carbonate (2 ml). 135 mg, 0.977 mmol) and 2- [4- (chloromethyl) phenoxy] -5- (trifluoromethyl) pyridine (205 mg, 0.713 mmol) were added at room temperature and stirred at the same temperature for 2 hours. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound as white crystals (yield 276 mg, yield 76%).

The following compound was synthesized according to the method of Example 24.
1- [2,4-Dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-[{4-[(5-trifluoromethyl) -2-pyridyloxy] phenyl} methyl] Piperazine (1-254)

<Example 25>
<1- (1,1,2,2-tetrafluoroethoxy) benzyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1- 732)>
To a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (200 mg, 0.649 mmol) in N, N-dimethylformamide (1 ml) was added potassium carbonate (1 ml). 135 mg, 0.977 mmol) and 4- (1,1,2,2-tetrafluoroethoxy) benzyl chloride (173 mg, 0.713 mmol) were added at room temperature and stirred at the same temperature for 3 hours. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/5) to give the title compound (yield 311 mg, 83%) as a yellow oil.

The following compound was synthesized according to the method of Example 25.
1- [4- (trifluoromethoxy) benzyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-728), 1- [ 4- (trifluoromethylthio) benzyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-738), 1- (3-chloro Benzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-807), 1- (2-chlorobenzyl) -4- [2 -Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-810), 1- (3,4-dichlorobenzyl) -4- [2-fluoro-4- Methyl-5- (2, , 2-trifluoroethylthio) phenyl] piperazine (1-814), 1- (4-methoxybenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) ) Phenyl] piperazine (1-722), 1- (2,3,4,5,6-pentafluorobenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoro) Ethylthio) phenyl] piperazine (1-825), 1- (4-iodobenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine ( 1-702), 1- (4-ethylbenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-708), 1- (2-ethylben L) -4- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-812), 1- (4-isopropylbenzyl) -4- [2 -Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-709), 1- (2,4,6-trimethylbenzyl) -4- [2-fluoro- 4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-847), 1-benzyl-4- [2-fluoro-4-methyl-5- (2,2,2) -Trifluoroethylthio) phenyl] piperazine (1-689), 1- (2,6-dichlorobenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) ) Phenyl] piperazine (1) -822), 1- (2,5-dichlorobenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-823), 1 -[4- (2,2,2-trifluoroethylthio) benzyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1- 740), 1- [4- (2,2,2-trifluoroethylsulfinyl) benzyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] Piperazine (1-745), 1- [4- (2,2,2-trifluoroethylsulfonyl) benzyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethyl) Thio) phenyl] piperazine (1-74 ), 1- (4-methylthiobenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-737), 1- (4- Methylsulfonylbenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-746), 1- [4- (isopropylsulfinyl) benzyl] -4- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-743), 1- [4- (isopropylsulfonyl) benzyl] -4- [ 2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-747), 1- (2,4-difluorobenzyl) -4- [2-fluoro-4 Methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-816), 1- (2-chloro-4-fluorobenzyl) -4- [2-fluoro-4-methyl-5 -(2,2,2-trifluoroethylthio) phenyl] piperazine (1-831), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl]- 4- (4-Chloro-2-fluorobenzyl) piperazine (1-828), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- ( 4-chloro-2-bromobenzyl) piperazine (1-829), 1- (2,4-dichlorobenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethyl) Thio) phenyl] pipera (1-818), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-fluorobenzyl) piperazine (1-690), 1- (4-Bromobenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-699), 1- [2-fluoro- 4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-[(4-trifluoromethyl) benzyl] piperazine (1-719), 1- [2-fluoro-4-methyl -5- (2,2,2-trifluoroethylthio) phenyl] -4- (cyanobenzyl) piperazine (1-703), 1- [2-fluoro-4-methyl-5- (2,2,2) -Trifluoroethylthio) phenyl] 4- (4-Nitrobenzyl) piperazine (1-704), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-methylbenzyl) ) Piperazine (1-705), N- {4- [4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazin-1-ylmethyl] benzyl} acetamide (1-714), 1- [2-Fluoro-4-methyl-5- (2,2,2, -trifluoroethylthio) phenyl] -4- (4-ethoxycarbonylbenzyl) piperazine (1-758) , 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- [2-fluoro-4-methyl-5- (2,2,2-tri Fluoroethylthio) Njiru] piperazine (1-741)

<Example 26>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-phenylbenzyl) piperazine (1-765)>
4-Phenyl was added to a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (200 mg, 0.649 mmol) in N, N-dimethylformamide (2 ml). Benzyl bromide (176 mg, 0.714 mmol) and potassium carbonate (108 mg, 0.781 mmol) were added at 0 ° C. and stirred overnight at room temperature. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/5) to give the title compound (yield 230 mg, 75%) as a pale yellow oil.

The following compound was synthesized according to the method of Example 26.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2-phenylbenzyl) piperazine (1-763), 1- [2-fluoro- 4-Methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (3-phenylbenzyl) piperazine (1-764)

<Example 27>
Synthesis of <1- [4- (3-chlorophenoxy) benzyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-772) >
To a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (200 mg, 0.649 mmol) in N, N-dimethylformamide (1 ml) was added potassium carbonate (1 ml). 135 mg, 0.977 mmol) and 4- (3-chlorophenoxy) benzyl chloride (181 mg, 0.715 mmol) were added at room temperature and stirred at the same temperature for 3 hours. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound (yield 203 mg, yield 60%) as a yellow candy.

The following compound was synthesized according to the method of Example 27.
1- [4- (2-chlorophenoxy) benzyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-774), 1- [3- (4-Chlorophenoxy) benzyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-776), 1- [2 -(4-Chlorophenoxy) benzyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-778), 1- [2-fluoro -4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- [4-[(3-trifluoromethyl) -2-pyridyloxy] benzyl] piperazine (1-800), 1- [2-Fluo -4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-[{4- (1,2,4-triazole) phenyl} methyl] piperazine (1-794), 1- [{6- (4-Chlorophenoxy) -3-pyridyl} methyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-888 ), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- [3- (4-methylphenoxy) benzyl] piperazine (1-781)

<Example 28>
<Synthesis of 1- [1- (4-chlorophenyl) ethyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-864)>
Carbonic acid was added to a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (0.30 g, 0.974 mmol) in N, N-dimethylformamide (5 ml). Potassium (200 mg, 1.46 mmol) and 1- (1-bromoethyl) -4-chlorobenzene (280 mg, 1.27 mmol) were added at room temperature and stirred at 50 ° C. for 1.5 hours. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/7) to give the title compound (yield 210 mg, 48%) as a pale yellow oil.

The following compound was synthesized according to the method of Example 28.
2- (4-Chlorophenyl) -2- [4- {2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl} piperazin-1-yl] acetonitrile (1-868) , 1- [1- (4-chlorophenyl) -2,2,2-trifluoroethyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] Piperazine (1-870), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- [1-ethyl (4-chlorobenzyl)] piperazine ( 1-866), methyl-2- (4-chlorophenyl) -2- [4- {2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl} piperazin-1-yl Acetate (1-872), - benzhydryl-4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethyl) phenyl] piperazine (1-874)

<Example 29>
<1-[(6-Chloro-3-pyridyl) methyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-882) Composition>
To a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (200 mg, 0.649 mmol) in N, N-dimethylformamide (1 ml) was added potassium carbonate (1 ml). 135 mg, 0.977 mmol) and 2-chloro-5-chloromethylpyridine (126 mg, 0.778 mmol) were added at room temperature and stirred at the same temperature for 3 hours. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound (yield 197 mg, yield 70%) as a yellow oil.

The following compound was synthesized according to the method of Example 29.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] 4- (3-thienylmethyl) piperazine (1-896), 1-[(4-quinolyl) Methyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-890), 1-[(6,8-difluoro-4-quinolyl) ) Methyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-893), 1-[(8-quinolyl) methyl] -4 -[2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-892), 1-[(6-quinolyl) methyl] -4- [2-fluoro -4-methyl-5- (2,2,2-to Fluoroethylthio) phenyl] piperazine (1-891), 1- (1-naphthylmethyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-324), 1- (2-chloro-5-thiazolylmethyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-900 ), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (1,2,3-benzothiadiazol-6-ylmethyl) piperazine (1- 903)

<Example 30>
<1- [3-Chloro-5- (trifluoromethyl) -2-pyridyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine ( Synthesis of 1-1274)>
To a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (200 mg, 0.649 mmol) in N, N-dimethylformamide (1 ml) was added potassium carbonate (1 ml). 135 mg, 0.977 mmol) and 2,3-dichloro-5-trifluoromethylpyridine (168 mg, 0.778 mmol) were added at room temperature and stirred at 50 ° C. for 2 hours. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/15) to give the title compound as white crystals (yield 271 mg, 86%).

The following compounds were synthesized according to the method of Example 30.
1- [2,3,5,6-tetrafluoro-4-pyridyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1- 1276), 1- [3-chloro-2,5,6-trifluoro-4-pyridyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl Piperazine (1-1280), 1- [5-chloro-3,4,6-trifluoro-2-pyridyl] -4- [2-fluoro-4-methyl-5- (2,2,2-tri) Fluoroethylthio) phenyl] piperazine (1-1283), 1- [3-chloro-5- (trifluoromethyl) -2-pyridyl] -4- [3- (2,2,2-trifluoroethylthio) Phenyl] piperazine (1-26)

<Example 31>
<Synthesis of 1- (4-chlorophenacyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-340)>
To a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (200 mg, 0.649 mmol) in N, N-dimethylformamide (1 ml) was added potassium carbonate (1 ml). 135 mg, 0.977 mmol) and 4-chlorophenacyl bromide (167 mg, 0.715 mmol) were added at room temperature and stirred at the same temperature for 1 hour. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/5) to give the title compound as white crystals (yield 278 mg, yield 93%).

The following compound was synthesized according to the method of Example 31.
1- (4-chlorophenyl) -2- {4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazin-1-yl} propan-1-one ( 1-352), 2- {4- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazin-1-yl} -2-methyl-1-phenylpropane -1-one (1-353), 1-phenacyl-4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-339), 1- (4-Bromophenacyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-348), 1- (4-methylphenacyl)- 4- [2-Fluoro-4- Til-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-349), 1- (4-chlorophenyl) -3- {4- [2-fluoro-4-methyl-5- ( 2,2,2-trifluoroethylthio) phenyl] piperazin-1-yl} propan-1-one (1-356), 1- [2-fluoro-4-methyl-5- (2,2,2- Trifluoroethylthio) phenyl] -4- [2-methoxy-2- (4-chlorophenyl) ethyl] piperazine (1-329), 1- [2- (4-chlorophenyl) ethyl] -4- [2-fluoro -4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-326), 1- (4-chlorocinnamyl) -4- [2-fluoro-4-methyl-5 -(2,2,2-Triflu Roechiruchio) phenyl] piperazine (1-333)

<Example 32>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (cyanomethyl) piperazine (1-315)>
To a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (300 mg, 0.973 mmol) in N, N-dimethylformamide (5 ml) was added potassium carbonate (5 ml). 240 mg, 1.76 mmol) and bromoacetonitrile (170 mg, 1.41 mmol) were added at 0 ° C. and stirred at room temperature for 1 hour. The reaction mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/4) to give the title compound (yield 270 mg, 80%) as a yellow oil.

The following compound was synthesized according to the method of Example 32.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2-cyanoethyl) piperazine (1-318), 1- [2-fluoro-4 -Methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-n-dodecylpiperazine (1-291), 1- [2-fluoro-4-methyl-5- (2,2, 2-trifluoroethylthio) phenyl] -4-cyclopropylmethylpiperazine (1-362), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl]- 4- (2-propenyl) piperazine (1-301), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2-propynyl) piperazine (1-303), methyl 2 {4- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperidin-1-yl} acetate (1-319), 1- [2-fluoro-4- Methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2,2-trifluoroethyl) piperazine (1-308), 1- [2-fluoro-4-methyl- 5- (2,2,2-trifluoroethylthio) phenyl] -4- (3,4,4-trifluoro-3-butenyl) piperazine (1-321), 1-cyclopropyl-2- [4- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazin-1-yl] ethanone (1-367), 1- [4- [2-fluoro-4- Methyl-5- (2,2,2-trifluoroethylthio ) Phenyl] piperazin-1-yl] -3,3-dimethyl-butan-2-one (1-366)

<Example 33>
<Synthesis of 1- (4-t-butylbenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-710)>
To a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (250 mg, 0.811 mmol) in N, N-dimethylformamide (1 ml) was added potassium carbonate (1 ml). 168 mg, 1.22 mmol) and 4-t-butylbenzyl bromide (203 mg, 0.894 mmol) were added at room temperature and stirred at the same temperature for 3 hours. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound as a yellow oil (yield 219 mg, yield 59%).

The following compound was synthesized according to the method of Example 33.
1- (4-t-butylbenzyl) -4- [3- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-22), 1- (4-t-butylbenzyl) -4- [2,4-Dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-250)

<Example 34>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (N-isopropylcarbamoyl) piperazine (1-613)>
Triethylamine (197 mg, 1.95 mmol) in dichloromethane solution (3 ml) of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (300 mg, 0.973 mmol) And isopropyl isocyanate (91.1 mg, 1.07 mmol) were added at 0 ° C. and stirred at room temperature for 4 hours. The reaction mixture was poured into water and extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to obtain the title compound (yield 222 mg, yield 58%) as a pale yellow crystal.

The following compound was synthesized according to the method of Example 34.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (N-4-chlorophenylcarbamoyl) piperazine (1-1091), 1- [2- Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (N-ethylcarbamoyl) piperazine (1-610), 1- [2-fluoro-4-methyl-5 -(2,2,2-trifluoroethylthio) phenyl] -4- (Nt-butylcarbamoyl) piperazine (1-616), 1- [2-fluoro-4-methyl-5- (2,2 , 2-trifluoroethylthio) phenyl] -4- (N-cyclohexylcarbamoyl) piperazine (1-618), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) Phenyl] -4- (N-2-chloroethylcarbamoyl) piperazine (1-619), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4 -(N-ethylthiocarbamoyl) piperazine (1-624), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (N-isopropylthio Carbamoyl) piperazine (1-626), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (Nt-butylthiocarbamoyl) piperazine ( 1-629), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (N-isobutylthiocarbamoyl) piperazine (1 628), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (N-cyclohexylthiocarbamoyl) piperazine (1-631), 1- [ 2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (N-methylthiocarbamoyl) piperazine (1-623), 1- [2-fluoro-4-methyl -5- (2,2,2-trifluoroethylthio) phenyl] -4- {N- [2-methyl-4- {1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl } Phenyl] carbamoyl} piperazine (1-908)

<Example 35>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (N-methylcarbamoyl) piperazine (1-608)>
Triphosgene (69 mg, 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (154 mg, 0.5 mmol) and 1 drop of pyridine in toluene (5 ml). 0.23 mmol) was added at 0 ° C., and the mixture was stirred at 80 ° C. for 3 hours. The reaction mixture was concentrated under reduced pressure. Triethylamine (253 g, 2.5 mmol) was added to a dichloromethane solution (5 ml) of the obtained concentrate and methylamine hydrochloride (101 mg, 1.5 mmol) at 0 ° C., and the mixture was stirred at room temperature for 8 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: methanol / chloroform = 1/100) to give the title compound as white crystals (yield 140 mg, 78%).

<Example 36>
<1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (3,3,3-trifluorothiopropionyl) piperazine (1-532) Composition>
Of 1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (3,3,3-trifluoropropionyl) piperazine (160 mg, 0.38 mmol) Lawesson's reagent (230 mg, 0.57 mmol) was added to a tetrahydrofuran solution (10 ml), and the mixture was stirred at room temperature for 1 hour. The reaction solution was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/4) to give the title compound (yield 110 mg, 66%) as a brown oil.

The following compound was synthesized according to the method of Example 36.
1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (thioisobutanoyl) piperazine (1-395), 1- [2-fluoro- 4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (cyclohexanethiocarbonyl) piperazine (1-420), 1- [2-fluoro-4-methyl-5- (2 , 2,2-trifluoroethylthio) phenyl] -4- (difluorothioacetyl) piperazine (1-527), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethyl) Thio) phenyl] -4- (4-chlorophenylthioacetyl) piperazine (1-552), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4 -(Thioacetyl) pipe Razine (1-371)

<Example 37>
<1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2-difluoro-1-methyl-cyclopropanethiocarbonyl) piperazine (1 -439) Synthesis>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2-difluoro-1-methyl-cyclopropanecarbonyl) piperazine (200 mg, 0 Lawson's reagent (379 mg, 0.937 mmol) was added to a tetrahydrofuran solution (2 ml) of .469 mmol) at 0 ° C., and the mixture was heated to reflux for 2 hours. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/4) to give the title compound (yield 210 mg, 100%) as a yellow candy.

The following compound was synthesized according to the method of Example 37.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2-dichloro-1-methylcyclopropanethiocarbonyl) piperazine (1-460 )

<Example 38>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-chlorothiobenzoyl) piperazine (1-1031)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-chlorobenzoyl) piperazine (500 mg, 1.12 mmol) in tetrahydrofuran (10 mL) Dissolved. Lawesson's reagent (450 mg, 1.12 mmol) was added at 0 ° C., and the mixture was stirred at room temperature for 1 hour. Furthermore, Lawesson's reagent (250 mg, 0.618 mmol) was added at 0 ° C., and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/5) to give the title compound (yield 520 mg, 100%) as a yellow candy.

<Example 39>
<Synthesis of t-butyl 4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazin-1-ylcarboxylate (1-600)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (200 mg, 0.649 mmol) in dichloromethane (3 ml) with triethylamine (131 mg, 1.30 mmol) And di-t-butyl dicarbonate (156 mg, 0.715 mmol) was added at 0 ° C. and stirred at room temperature for 2 hours. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/4) to give the title compound as a colorless oil (yield 249 mg, 94%).

<Example 40>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2,2-trifluoroacetyl) piperazine (1-528) >
Triethylamine (197 mg, 1.95 mmol) in dichloromethane solution (3 ml) of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (300 mg, 0.973 mmol) And trifluoroacetic anhydride (224 mg, 1.07 mmol) were added at 0 ° C. and stirred at room temperature for 4 hours. The reaction mixture was poured into water and extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to obtain the title compound as a pale yellow crystal (yield 330 mg, 84%).

<Example 41>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (isopentanoyl) piperazine (1-397)>
To a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (300 mg, 0.97 mmol) in dichloromethane (5 ml) was added 1- (3-dimethylamino Propyl) -3-ethylcarbodiimide hydrochloride (210 mg, 1.07 mmol), isovaleric acid (110 mg, 1.07 mmol), triethylamine (150 mg, 1.46 mmol) were added at 0 ° C., and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/1) to give the title compound as a brown oil (yield 320 mg, 84%).

The following compound was synthesized according to the method of Example 41.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-[(cyclohexyl) acetyl] piperazine (1-547), 1- [2-fluoro- 4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-[(2-oxocyclopentyl) acetyl] piperazine (1-544), 1- [2-fluoro-4-methyl- 5- (2,2,2-trifluoroethylthio) phenyl] -4- [3- (4-chlorobenzoyl) propionyl] piperazine (1-583), 1- [2-fluoro-4-methyl-5 (2,2,2-trifluoroethylthio) phenyl] -4- (2,2,3,3,3-pentafluoropropanoyl) piperazine (1-539), 1- [2-fluoro-4-methyl -5- ( , 2,2-trifluoroethylthio) phenyl] -4- (4,4,4-trifluorobutanoyl) piperazine (1-540), 1- [2-fluoro-4-methyl-5- (2, 2,2-trifluoroethylthio) phenyl] -4- (2-methylbutanoyl) piperazine (1-401)

<Example 42>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2-trifluoromethylacryloyl) piperazine (1-595)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (500 mg, 1.62 mmol) in dichloromethane (10 ml) was added to 1- (3-dimethylamino Propyl) -3-ethylcarbodiimide hydrochloride (340 mg, 1.78 mmol), 2- (trifluoromethyl) acrylic acid (250 mg, 1.78 mmol), triethylamine (250 mg, 2.43 mmol) were added at 0 ° C. and room temperature. For 5 hours. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/2) to give the title compound (yield 70 mg, 10%) as a brown oil.

The following compound was synthesized according to the method of Example 42.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (acryloyl) piperazine (1-587), 1- [2-fluoro-4-methyl -5- (2,2,2-trifluoroethylthio) phenyl] -4-[(E) -3-chloro-2-propenoyl] piperazine (1-594), 1- [2-fluoro-4-methyl -5- (2,2,2-trifluoroethylthio) phenyl] -4-[(Z) -2-butenoyl] piperazine (1-589)

<Example 43>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2-tetrahydrofurancarbonyl) piperazine (1-1023)>
To a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (400 mg, 1.30 mmol) in dichloromethane (10 ml) was added 1- (3-dimethylamino Propyl) -3-ethylcarbodiimide hydrochloride (270 mg, 1.43 mmol), tetrahydrofuran-2-carboxylic acid (170 mg, 1.43 mmol), triethylamine (200 mg, 1.95 mmol) were added at 0 ° C., and 2 hours at room temperature. Stir. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (elution solvent: ethyl acetate / n-hexane = 1/1) to obtain the title compound as a brown oil (yield 340 mg, yield 64%).

The following compound was synthesized according to the method of Example 43.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (1,2,3-benzothiadiazolyl-5-carbonyl) piperazine (1- 1021), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,1,3-benzothiadiazolyl-5-carbonyl) piperazine (1-1022), 1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (1,2-benzisothiazole-3-carbonyl) piperazine (1-1020), 1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-tetrahydropyrancarbonyl) piperazine (1-1025)

<Example 44>
<1- (2,2-Difluoro-1-methyl-cyclopropanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1- 436)>
To a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (700 mg, 2.27 mmol) in dichloromethane (10 ml) was added 2,2-difluoro-1- Methylcyclopropanecarboxylic acid (obtained according to the method described in Journal of Fluorine Chemistry 49 127-139 (1990)) (370 mg, 2.72 mmol), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (653 mg, 3.41 mmol), 4-dimethylaminopyridine (27.7 mg, 0.22 mmol) and triethylamine (689 mg, 6.81 mmol) were added at 0 ° C. and stirred at room temperature for 12 hours. The reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (elution solvent: ethyl acetate / n-hexane = 1/2) to obtain the title compound as white crystals (yield 430 mg, yield 44%).

The following compound was synthesized according to the method of Example 44.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4,4-difluorocyclohexanecarbonyl) piperazine (1-507), 1- [2 -Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (1-methylcyclohexanecarbonyl) piperazine (1-423), 1- [2-fluoro-4-methyl -5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-methylcyclohexanecarbonyl) piperazine (1-425), 1- [2-fluoro-4-methyl-5- (2, 2,2-trifluoroethylthio) phenyl] -4- (cyclobutanecarbonyl) piperazine (1-412), 1- [2-fluoro-4-methyl-5- (2,2,2-tri (Luoroethylthio) phenyl] -4- (cyclopentanecarbonyl) piperazine (1-415), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- ( 4,4-difluoro-1-methylcyclohexanecarbonyl) piperazine (1-509,1-510), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (3,3-difluorocyclopentanecarbonyl) piperazine (1-500), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (3,3-difluoro-1-methylcyclopentanecarbonyl) piperazine (1-502), 1- (2,2-difluoro-1-methyl-cyclopropane carbonate Boniru) -4- [2-fluoro-4-methyl-5- (pentafluoroethyl) phenyl] piperazine (2-332)

<Example 45>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-fluorophenylacetyl) piperazine (1-561)>
L- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (150 mg, 0.486 mmol) in dichloromethane (2 ml) was added 4-fluorophenylacetic acid (82 mg, 0.532 mmol), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (140 mg, 0.730 mmol), 4-dimethylaminopyridine (6.0 mg, 0.0491 mmol) and triethylamine (148 mg, 1. 47 mmol) was added at 0 ° C. and stirred at room temperature for 5 hours. The reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/1) to give the title compound as a yellow oil (yield 146 mg, yield 68%).

The following compound was synthesized according to the method of Example 45.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2-chlorophenylacetyl) piperazine (1-554), 1- [2-fluoro- 4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (3-chlorophenylacetyl) piperazine (1-555), 1- [2-fluoro-4-methyl-5- ( 2,2,2-trifluoroethylthio) phenyl] -4- (3,4-dichlorophenylacetyl) piperazine (1-556), 1- [2-fluoro-4-methyl-5- (2,2,2) -Trifluoroethylthio) phenyl] -4- (2,4-dichlorophenylacetyl) piperazine (1-558), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) ) Phenyl] -4- (4-trifluoromethylphenylacetyl) piperazine (1-560), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl]- 4- (4-Bromophenylacetyl) piperazine (1-563), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-methoxy Phenylacetyl) piperazine (1-564), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-methylphenylacetyl) piperazine (1 -565), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,4,6-trimethylphenylacetyl) pipera (1-566), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-chlorophenoxyacetyl) piperazine (1-584) 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,4-dichlorophenoxyacetyl) piperazine (1-586), 1- [ 2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- [3- (4-chlorophenyl) -2-propenoyl] piperazine (1-597)

<Example 46>
<1- (3,3,3-trifluoro-2,2-dimethylpropanoyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine Synthesis of (1-536)>
To a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (400 mg, 1.30 mmol) in N, N-dimethylformamide (2 ml), 3,3 , 3-trifluoro-2,2-dimethylpropionic acid (220 mg, 1.43 mmol), N, N-diisopropylethylamine (670 mg, 5.19 mmol) and 1H-benzotriazol-1-yloxytris (dimethylamino) phosphonium Hexafluorophosphate (690 mg, 1.56 mmol) was added at room temperature and stirred at room temperature for 1 hour. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound (yield 310 mg, 54%) as a yellow oil.

The following compound was synthesized according to the method of Example 46.
1- (2,2-dimethylbutanoyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-383), 1- (2 , 2-dimethylpentanoyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-385), 1-nonanoyl-4- [2 -Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-379), 1-tridecanoyl-4- [2-fluoro-4-methyl-5- (2, 2,2-trifluoroethylthio) phenyl] piperazine (1-381), 1-methacryloyl-4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1 590), 1- (cyanoacetyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-543), 1- (3,3 , 3-trifluoropropanoyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-530), 1- (2,2- Difluoroacetyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-525), 1- [2-fluoro-4-methyl-5 -(2,2,2-trifluoroethylthio) phenyl] -4- (3- (4-chlorophenyl) propanoyl) piperazine (1-568)

<Example 47>
<Synthesis of 1- (4-chlorophenylacetyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-549)>
4-chlorophenyl was added to a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (300 mg, 0.974 mmol) in N, N-dimethylformamide (3 ml). Acetic acid (180 mg, 1.07 mmol), N, N-diisopropylethylamine (500 mg, 3.90 mmol) and 1H-benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate (470 mg, 1.07 mmol). The mixture was added at room temperature and stirred at room temperature for 3 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/7) to give the title compound (yield 390 mg, yield 87%) as a yellow oil.

The following compound was synthesized according to the method of Example 47.
1- (4-Chlorophenyl) -2- [4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazin-1-yl] ethane-1,2- Dione (1-573), 1- [2- (4-chlorophenyl) -2-fluoroacetyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl Piperazine (1-569), 1- [2- (4-chlorophenyl) -2,2-difluoroacetyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethyl) Thio) phenyl] piperazine (1-571), 1- [2- (4-chlorophenyl) -2-methoxyiminoacetyl] -4- [2-fluoro-4-methyl-5- (2,2,2-tri) Fluoroethylthio) phenyl] Perazine (1-582), 1- [2- (4-chlorophenyl) -2-methoxyacetyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl Piperazine (1-579), 1- [2- (4-chlorophenyl) -2-methylthioacetyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) Phenyl] piperazine (1-580), 1- [2- (4-chlorophenyl) propanoyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-575), 1- [2- (4-Chlorophenyl) -2-methylpropanoyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl ] Perazine (1-577)

<Example 48>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl-4- (1-trifluoromethylcyclopropanecarbonyl) piperazine (1-487)>
1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (277 mg, 0.9 mmol), N, N-diisopropylethylamine (464 mg, 3.6 mmol) and To a solution of 1-trifluoromethylcyclopropanecarboxylic acid (139 mg, 0.9 mmol) in N, N-dimethylformamide (10 ml) was added 1H-benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate (477 mg, 1.08 mmol) was added at 0 ° C. and stirred at room temperature for 5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/5) to give the title compound (yield 230 mg, yield 58%) as a pale yellow oil.

The following compound was synthesized according to the method of Example 48.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2,3,3-tetramethylcyclopropanecarbonyl) piperazine (1-432 ), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- [3- (2,2-dichlorovinyl) -2,2-dimethylcyclo Propanecarbonyl] piperazine (1-492), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2-dichloro-3,3 -Dimethylcyclopropanecarbonyl) piperazine (1-483), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (3-methyl-2- Butenoyl) Pipe Gin (1-593), 1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2-dibromo-1-methylcyclopropanecarbonyl ) Piperazine (1-474), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (1-cyano-2-trifluoromethylcyclopropane) Carbonyl) piperazine (1-491), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2-bromo-2-iodo-1- Methylcyclopropanecarbonyl) piperazine (1-478), 1- (cyclohexanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl Piperazine (1-418), 1- (cycloheptanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-421), 1 -(1-methylcyclopropanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-427), 1- [2,2 -Dichloro-1- (4-chlorophenyl) cyclopropanecarbonyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-485), 1 -[2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2-dichloro-1,3-dimethylcyclopropanecarbonyl) pi Perazine (1-484), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2-dichlorocyclopropanecarbonyl) piperazine (1 -453), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (1,1,1-trifluoromethylcyclohexanecarbonyl) piperazine (1 -518), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (1,1,1-trifluoromethylcyclopentanecarbonyl) piperazine ( 1-504), 1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (1,1,1-trifluoromethylcyclobutane Rubonyl) piperazine (1-493), 1- (1-ethyl-2,2-difluorocyclopropanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) ) Phenyl] piperazine (1-442), 1- (1-ethyl-2,2-dichlorocyclopropanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethyl) Thio) phenyl] piperazine (1-463), 1- (2,2-difluorocyclopropanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl Piperazine (1-433), 1- (1-isopropyl-2,2-difluorocyclopropanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2- Trifluoroethylthio) phenyl] piperazine (1-447), 1- (1-butyl-2,2-difluorocyclopropanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2) -Trifluoroethylthio) phenyl] piperazine (1-446), 1- (1-cyclopentyl-2,2-difluorocyclopropanecarbonyl) -4- [2-fluoro-4-methyl-5- (2,2, 2-trifluoroethylthio) phenyl] piperazine (1-448), 1- [2,2-difluoro-1- (trifluoromethyl) cyclopropanecarbonyl] -4- [2-fluoro-4-methyl-5 (2,2,2-trifluoroethylthio) phenyl] piperazine (1-449), 1- (3,3,3-trifluoroisobutanoyl) -4- [2-fluoro -4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-534), 1- [2-bromo-1-methylcyclopropanecarbonyl] -4- [2-fluoro- 4-Methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-472, 1-473)

<Example 49>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-fluorobenzoyl) piperazine (1-905)>
1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (154 mg, 0.5 mmol), N, N-diisopropylethylamine (160 mg, 1.25 mmol) and 1-H-benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate (265 mg, 0.6 mmol) in a solution of 4-fluorobenzoic acid (70 mg, 0.5 mmol) in N, N-dimethylformamide (5 ml) Was added at 0 ° C. and stirred at room temperature for 4 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound (yield 170 mg, 77%) as a pale yellow oil.

The following compound was synthesized according to the method of Example 49.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2-chloroisonicotinoyl) piperazine (1-1011), 1- [2- Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2-bromoisonicotinoyl) piperazine (1-1013), 1- [2-fluoro-4-methyl -5- (2,2,2-trifluoroethylthio) phenyl] -4- (6-trifluoromethylnicotinoyl) piperazine (1-1009), 1- [2-fluoro-4-methyl-5- ( 2,2,2-trifluoroethylthio) phenyl] -4- (6-bromonicotinoyl) piperazine (1-1007), 1- [2-fluoro-4-methyl-5- (2,2,2- Trifluoroethylthio ) Phenyl] -4- (4-chloro-3-fluorobenzoyl) piperazine (1-968), 1- (2-methylthiooxazole-4-carbonyl) -4- [2-fluoro-4-methyl-5- ( 2,2,2-trifluoroethylthio) phenyl] piperazine (1-1017), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-Tetrahydrothiopyrancarbonyl) piperazine (1-1027), t-butyl 4- [4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine- 1-Carbonyl] piperidine-1-carboxylate (1-1028)

<Example 50>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (trifluoromethylsulfonyl) piperazine (1-666)>
To a solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (150 mg, 0.486 mmol) in dichloromethane (3 ml) was added triethylamine (98.0 mg, 0.0. 970 mmol) and trifluoromethanesulfonic anhydride (206 mg, 0.730 mmol) were added at 0 ° C. and stirred at the same temperature for 30 minutes. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/5) to give the title compound as white crystals (yield 122 mg, 57%).

The following compound was synthesized according to the method of Example 50.
1- (2-Fluoro-4-methyl-5-methylthiophenyl) -4- (trifluoromethylsulfonyl) piperazine (2-15), 1- [2-fluoro-4-methyl-5- (allylthio) phenyl] -4- (trifluoromethylsulfonyl) piperazine (2-88), 1- {2-fluoro-4-methyl-5-[(propyn-2-yl) thio] phenyl} -4- (trifluoromethylsulfonyl) Piperazine (2-115), 1- [2-fluoro-4-methyl-5- (cyanomethylthio) phenyl] -4- (trifluoromethylsulfonyl) piperazine (2-142), 1- [2,4-dimethyl -5- (2,2,2-trifluoroethylthio) phenyl] -4- (trifluoromethylsulfonyl) piperazine (1-241), 4- [2-fluoro -4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -3-methyl-1- (trifluoromethylsulfonyl) piperazin-2-one (3-266), 1- [4- Methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (trifluoromethylsulfonyl) piperazine (1-217), 1- [2-fluoro-4-methyl-5- (cyclopropyl) Methylthio) phenyl] -4- (trifluoromethylsulfonyl) piperazine (2-238), 1- [2-fluoro-4-methyl-5- (4-chlorobenzylthio) phenyl] -4- (trifluoromethylsulfonyl) ) Piperazine (2-199), 1- [2-fluoro-4-methyl-5- (3,3,3-trifluoropropylthio) phenyl] -4- (trifluoro Methylsulfonyl) piperazine (2-367), 4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -2-methyl-1- (trifluoromethylsulfonyl) Piperazine (3-47), 1- [2,4-difluoro5- (2,2,2-trifluoroethylthio) phenyl] -4- (trifluoromethanesulfonyl) piperazine (1-1340), 1- [2 -Fluoro-4-methyl-5- (isobutylthio) phenyl] -4- (trifluoromethylsulfonyl) piperazine (2-62), 1- [2-fluoro-4-methyl-5- (2,2,2) -Trifluoroethylthio) phenyl] -2-methyl-4- (trifluoromethylsulfonyl) piperazine (3-15), 1- [5-[(2,2-dichloro-1-methyl) Cyclopropyl) methylthio] -2-fluoro-4-methylphenyl] -4- (trifluoromethylsulfonyl) piperazine (2-256), 1- [2-fluoro-4-methyl-5- (pentafluoroethylthio) Phenyl] -4- (trifluoromethylsulfonyl) piperazine (2-338)

<Example 51>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (chlorosulfonyl) piperazine (1-640)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1.00 g, 3.24 mmol) in dichloromethane (30 ml) was dissolved in sulfuryl chloride (415 mg, 3 0.08 mmol) was added at −60 ° C., and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was poured into water and extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/7) to obtain the title compound as a pale yellow crystal (yield 643 mg, yield 49%).

<Example 52>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (N, N-diethylaminosulfonyl) piperazine (1-685)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (chlorosulfonyl) piperazine (25.0 mg, 61.4 μmol) in diethylamine solution (1 ml) And stirred at room temperature overnight. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/4) to give the title compound as a pale yellow oil (yield 26.1 mg, yield 96%).

The following compound was synthesized according to the method of Example 52.
1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2,2-trifluoroethylaminosulfonyl) piperazine (1-680), 1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (benzylaminosulfonyl) piperazine (1-682)

<Example 53>
<Synthesis of 1- (4-chlorophenyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-1213)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (400 mg, 1.30 mmol) and 4-chloroiodobenzene (465 mg, 1.95 mmol) in toluene To the solution (3 ml) was added sodium t-butoxide (187 mg, 1.95 mmol), tris (dibenzylideneacetone) palladium (60.0 mg, 0.0655 mmol) and 2- (di-t-butylphosphino) biphenyl (39.0 mg). 0.130 mmol) at room temperature and stirred at 80 ° C. for 5 hours under a nitrogen atmosphere. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/15) to give the title compound as white crystals (yield 191 mg, yield 35%).

The following compound was synthesized according to the method of Example 53.
1- (4-chlorophenyl) -4- [2,4-dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-263), 1- (3-chlorophenyl) -4- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-1240), 1- (2-chlorophenyl) -4- [2-fluoro-4-methyl -5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-1243), 1- (3,4-dichlorophenyl) -4- [2-fluoro-4-methyl-5- (2, 2,2-trifluoroethylthio) phenyl] piperazine (1-1246), 1- (4-tert-butylphenyl) -4- [2-fluoro-4-methyl-5- (2,2,2-tri Fluoroethylthio) fe L] piperazine (1-1218), 1- (4-methoxyphenyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-1223) ), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] 4- (3-pyridyl) piperazine (1-1266), 1- [2-fluoro- 4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] 4- (4-pyridyl) piperazine (1-1268), 1- [2-fluoro-4-methyl-5- (2, 2,2-trifluoroethylthio) phenyl] 4- (3-thienyl) piperazine (1-1287)

<Example 54>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-chloro-3-fluorobenzyl) piperazine (1-827)>
4-Chloro-3-fluorobenzaldehyde was added to a dichloromethane solution (2 ml) of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (200 mg, 0.649 mmol). (103 mg, 0.649 mmol) and sodium triacetoxyborohydride (206 mg, 0.974 mmol) were added at 0 ° C. and stirred overnight at room temperature. The reaction mixture was poured into water and extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/4) to give the title compound as a pale yellow oil (yield 65.4 mg, yield 22%).

The following compound was synthesized according to the method of Example 54.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] 4- (2-thienylmethyl) piperazine (1-894), 1-[(5-chloro- 2-thienyl) methyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-898), 1- (3,5-dichlorobenzyl ) -4- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-821), 1- (2,3-dichlorobenzyl) -4- [ 2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-824), 1- (4-bromo-2-fluorobenzyl) -4- [2-fluoro -4-methyl-5- (2,2, -Trifluoroethylthio) phenyl] piperazine (1-832), 1- (2-fluoro-4-methoxybenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoro) Ethylthio) phenyl] piperazine (1-837), 1- (3-bromo-4-methoxybenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) Phenyl] piperazine (1-838), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (3-phenylpropyl) piperazine (1-336) ), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (1,3-benzodioxol-5-ylmethyl) piperazine (1- 72 ), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2,2-difluoro-1,3-benzodioxol-5 Ylmethyl) piperazine (1-727), 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (1H-indol-5-ylmethyl) piperazine ( 1-901), 1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (1H-indol-6-ylmethyl) piperazine (1-902) 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-chloro-3-trifluoromethylbenzyl) piperazine (1-840), 1- [2-full Ro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-chloro-2,6-difluorobenzyl) piperazine (1-830), 1- [2-fluoro -4-methyl-5- (2,2,2, -trifluoroethylthio) phenyl] -4- (2-fluoro-4-trifluoromethylbenzyl) piperazine (1-858)

<Example 55>
<Synthesis of 1- [2-cyano-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (trifluoromethylsulfonyl) piperazine (1-133)>
1- [2-Bromo-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (trifluoromethylsulfonyl) piperazine (400 mg, 0.798 mmol) in toluene (1 ml) Were added copper iodide (15 mg, 0.0788 mmol), potassium hexacyanoferrate (II) (59 mg, 0.160 mmol) and 1-butylimidazole (198 mg, 1.59 mmol) at room temperature, and heated to reflux in a nitrogen atmosphere. did. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/7) to give the title compound (153 mg, 43% yield) as white crystals.

<Example 56>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-chlorobenzyl) piperazine-4-ium chloride (1-697) >
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-chlorobenzyl) piperazine (217 mg, 0.501 mmol) in ethyl acetate (2 ml) ) Hydrogen chloride
(1N ethyl acetate solution) (0.501 ml, 0.501 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was subjected to suction filtration and washed with ethyl acetate to obtain the title compound as white crystals (yield 123 mg, yield 52%).

The following compound was synthesized according to the method of Example 56.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-chlorobenzyl) piperazine-4-ium trifluoromethanesulfonate (1-698)

<Example 57>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- [4- (4-chlorophenyl) benzyl] piperazine (1-766)>
Toluene solution (3 ml) of 1- (4-iodobenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (300 mg, 0.572 mmol) 4-chlorophenylboronic acid (130 mg, 0.858 mmol), potassium carbonate (159 mg, 1.15 mmol) and tetrakis (triphenylphosphine) palladium (0) (66.1 mg, 0.0572 mmol) were added under a nitrogen atmosphere. Stir at 100 ° C. for 13 hours. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/6) to give the title compound (yield 110 mg, 38%) as a yellow oil.

The following compound was synthesized according to the method of Example 57.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- [4- (3-chlorophenyl) benzyl] piperazine (1-767), 1- [ 2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- [4- (2-chlorophenyl) benzyl] piperazine (1-768)

<Example 58>
<1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-[(2-methoxyiminocyclopentyl) acetyl] piperazine (1-545, 1-546 )
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-[(2-oxocyclopentyl) acetyl] piperazine (220 mg, 0.509 mmol) in tetrahydrofuran- Methoxyamine hydrochloride (128 mg, 1.53 mmol) was added to the aqueous mixed solution (2 ml) at room temperature, and the mixture was heated to reflux for 5 hours. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (elution solvent: ethyl acetate / n-hexane = 1/2) to give a yellow oily title compound (yield 176 mg, 66%) having low polarity and high polarity. The title compound (30 mg, 11%) was obtained as a yellow oil.

The following compound was synthesized according to the method of Example 58.
1- (4-Chlorophenyl) -2- [4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazin-1-yl] -N-methoxy-ethanimine (1-331, 1-332)

<Example 59>
<Synthesis of 2- {4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazin-1-yl} -1-phenylethanol (1-330)>
1- (4-Chlorophenacyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (2.38 g, 5.16 mmol) in methanol (1 ml) was added with sodium borohydride (215 mg, 5.68 mmol) at 0 ° C. and stirred at the same temperature for 1 hour. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound (yield 2.32 g, yield 97%) as a yellow oil.

<Example 60>
<1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-hydroxypiperazine (1-635) and 1- [2-fluoro-4-methyl- Synthesis of 5- (2,2,2-trifluoroethylsulfinyl) phenyl] -4-hydroxypiperazine (1-636)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (2-cyanoethyl) piperazine (1.75 g, 4.84 mmol) in dichloromethane (5 ml) ) Were added potassium carbonate (736 mg, 5.33 mmol) and 70% 3-chloroperbenzoic acid (1.31 g, 5.31 mmol) at 0 ° C., and the mixture was stirred at room temperature for 10 hours. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/1) to give white crystalline 1- [2-fluoro-4-methyl-5- (2,2,2- Trifluoroethylthio) phenyl] -4-hydroxypiperazine (yield 384 mg, 24% yield) and 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenyl]- 4-hydroxypiperazine (yield 224 mg, yield 14%) was obtained.

<Example 61>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4-carbamoylpiperazine (1-606)>
A toluene solution of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1308 mg, 1.0 mmol) and potassium cyanate (162 mg, 2.0 mmol) ( 5 ml) was added trifluoroacetic acid (228 mg, 2.0 mmol) at 0 ° C. and stirred at room temperature for 4 hours. Furthermore, potassium cyanate (162 mg, 2.0 mmol) and trifluoroacetic acid (228 mg, 2.0 mmol) were added to the reaction mixture, and the mixture was stirred for 2 hours. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: methanol / chloroform = 1/30) to give the title compound as white crystals (yield 180 mg, 51%).

<Example 62>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] 2-methylpiperazine (3-1)>
4- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -3-methylpiperazin-2-one (340 mg, 1.01 mmol) in diethyl ether (10 ml) Was added lithium aluminum hydride (120 mg, 3.04 mmol) at 0 ° C. and stirred at room temperature for 7 hours. The reaction mixture was slowly poured into a cold saturated potassium sodium tartrate aqueous solution, filtered through celite, and extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (elution solvent: methanol / chloroform = 1/50) to obtain the title compound as a brown oil (yield 64 mg, yield 20%).

<Example 63>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-aminobenzyl) piperazine (1-750)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-nitrobenzyl) piperazine (1.3 g, 3.07 mmol) in ethanol ( 10 ml) were added iron powder (1.03 g, 18.4 mmol) and concentrated hydrochloric acid (0.1 ml) at room temperature, and the mixture was stirred for 14 hours while heating under reflux. The reaction mixture was cooled and then filtered, and the filtrate was concentrated under reduced pressure. Water was poured into the concentrate and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: triethylamine / ethyl acetate / n-hexane = 0.02 / 1/3) to give the title compound (yield 440 mg, 35%) as a yellow oil. .

<Example 64>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-methylaminobenzyl) piperazine (1-751)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-aminobenzyl) piperazine (250 mg, 0.605 mmol) and sodium methoxide methanol solution A methanol solution (2 ml) of paraformaldehyde (25 mg, 0.847 mmol) was added to a methanol solution (4 ml) of (580 mg, 3.02 mmol) at room temperature, and stirred at the same temperature for 5 hours and with heating under reflux for 1 hour. After cooling to room temperature, sodium borohydride (23 mg, 0.605 mmol) was added, and the mixture was stirred for 3 hours with heating under reflux. After cooling to room temperature, water was added to the reaction mixture, and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound (yield 100 mg, yield 42%) as a yellow oil.

The following compound was synthesized according to the method of Example 64.
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-isopropylaminobenzyl) piperazine (1-752)

<Example 65>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-dimethylaminobenzyl) piperazine (1-754)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-aminobenzyl) piperazine (200 mg, 0.484 mmol) in toluene solution (5 ml) Dimethyl sulfate (130 mg, 1.07 mmol) and potassium carbonate (170 mg, 1.21 mmol) were added at room temperature and stirred at 70 ° C. for 1 hour. After cooling to room temperature, dimethyl sulfate (60 mg, 0.484 mmol) and potassium carbonate (70 mg, 0.484 mmol) were added and stirred at 70 ° C. for 2 hours. After cooling to room temperature and filtering the reaction mixture, the filtrate was concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound (yield 12.0 mg, yield 5.6%) as a yellow oil.

<Example 66>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-propargylaminobenzyl) piperazine (1-753)>
1- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -4- (4-aminobenzyl) piperazine (230 mg, 0.557 mmol) of N-methyl 2- To the pyrrolidinone solution (2 ml) were added propargyl bromide (66 mg, 0.557 mmol) and potassium carbonate (77 mg, 0.557 mmol) at room temperature, and the mixture was stirred at the same temperature for 1.5 hours. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: triethylamine / ethyl acetate / n-hexane = 0.02 / 1/4) to give the title compound (yield 24.3 mg, yield 10%) as a yellow oil. Obtained.

<Example 67>
<2- (4-Chlorophenyl) -2- [4- {2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl} piperazin-1-yl] acetic acid (1-873 )
Methyl 2- (4-chlorophenyl) -2- [4- {2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl} piperazin-1-yl] acetate (1.70 g) 3. To a methanol solution (5 ml) of 3.46 mmol), an aqueous solution (5 ml) of sodium hydroxide (0.27 g, 6.76 mmol) was added at 0 ° C. and stirred at room temperature for 2 hours. 2N hydrochloric acid was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: methanol / chloroform = 1/5) to give the title compound (yield 1.24 g, 77%) as a brown oil.

<Example 68>
<Synthesis of 4-{[4- {2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl} piperazin-1-yl] methyl} benzoic acid>
1- [2-Fluoro-4-methyl-5- (2,2,2, -trifluoroethylthio) phenyl] -4- (4-ethoxycarbonylbenzyl) piperazine (1.11 g, 2.36 mmol) in ethanol To the (10 mL) solution, an aqueous solution (5 ml) of sodium hydroxide (0.19 g, 4.72 mmol) was added at 0 ° C. and stirred at room temperature for 30 minutes. The reaction mixture was poured into water, the neutral zone was removed with chloroform, and the aqueous layer was adjusted to pH 1 with 1N hydrochloric acid. The aqueous layer was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was washed with hexane to obtain the title compound as an off-white powder (yield 0.77 g, yield 74%).

<Example 69>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2, -trifluoroethylthio) phenyl] -4- (4-methylaminocarbonylbenzyl) piperazine (1-760)>
4-{[4- {2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl} piperazin-1-yl] methyl} benzoic acid (200 mg, 0.45 mmol) in dichloromethane To the solution (5 ml) was added 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (180 mg, 0.95 mmol), methylamine hydrochloride (100 mg, 1.42 mmol) and triethylamine (250 mg, 2.49 mmol). Was added at 0 ° C., stirred at room temperature for 1 hour, and then heated to reflux for 5 hours. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: methanol / chloroform = 1/10) to give the title compound (yield 76 mg, 18%) as a brown oil.

The following compound was synthesized according to the method of Example 69.
1- [2-Fluoro-4-methyl-5- (2,2,2, -trifluoroethylthio) phenyl] -4- [4- (2,2,2-trifluoroethylaminocarbonyl) benzyl] piperazine (1-761), 1- [2-Fluoro-4-methyl-5- (2,2,2, -trifluoroethylthio) phenyl] -4- [4- (4-chlorobenzylaminocarbonyl) benzyl] Piperazine (1-762)

<Example 70>
<1- [2- (4-Chlorophenyl) -2-methylsulfinylacetyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1- 581)>
1- [2- (4-Chlorophenyl) -2-methylthioacetyl] -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (410 mg, 0. 809 mmol) in dichloromethane (8 ml) was added 70% 3-chloroperbenzoic acid (240 mg, 1.05 mmol) at 0 ° C. and stirred at the same temperature for 2 hours. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: methanol / chloroform = 1/50) to obtain the title compound (yield 240 mg, 57%) as a yellow oil.

The following compound was synthesized according to the method of Example 70.
1- (2-Methylsulfinyloxazole-4-carbonyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-1018)

<Example 71>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-276)>
Bis (2-chloroethyl) amine hydrochloride in a solution of 2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) aniline (3.58 g, 15.0 mmol) in diethylene glycol monomethyl ether (5 ml) (2.70 g, 15.1 mmol) was added and stirred at 150 ° C. for 10 hours. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: methanol / chloroform = 1/5) to give the title compound as a brown oil (yield 4.00 g, 86%).

The following compound was synthesized according to the method of Example 71.
1- (2-fluoro-4-methyl-5-methylthiophenyl) piperazine (2-1), 1- [2-fluoro-4-methyl-5- (allylthio) phenyl] piperazine (2-75), 1- {2-Fluoro-4-methyl-5-[(propyn-2-yl) thio] phenyl} piperazine (2-101), 1- [2-fluoro-4-methyl-5- (cyanomethylthio) phenyl] piperazine (2-128), 1- [3- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-1), 1- [2-chloro-5- (2,2,2-trifluoro) Ethylthio) phenyl] piperazine (1-1366), 1- [2,4-dimethyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-225)

<Example 72>
<Synthesis of 1- [2-fluoro-4-methyl-5- (cyclopropylmethylthio) phenyl] piperazine (2-218)>
2-Fluoro-4-methyl-5- (cyclopropylmethylthio) aniline (1.50 g, 7.10 mmol) in N-methyl-2-pyrrolidinone (5 ml) was added to bis (2-chloroethyl) amine hydrochloride (1. 27 g, 7.11 mmol) was added and stirred at 150 ° C. for 5 hours. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: methanol / chloroform = 1/5) to give the title compound (yield 1.30 g, yield 65%) as a brown oil.

The following compound was synthesized according to the method of Example 72.
1- [4-Methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-201), 1- [2-fluoro-4-methyl-5- (4-chlorobenzylthio) Phenyl] piperazine (2-196), 1- [5-{(2,2-dichloro-1-methylcyclopropyl) methylthio} -2-fluoro-4-methylphenyl] piperazine (2-252), 1- [ 2,4-difluoro-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-1326), 1- [2-fluoro-4-methyl-5- (isobutylthio) phenyl] piperazine ( 2-45), 1- [2-fluoro-4-methyl-5- (3,3,3-trifluoropropylthio) phenyl] piperazine (2-350), 1- [2-fluoro-4-methyl- 5- (3 , 3,3-trifluoropropylthio) phenyl] piperazine (2-347)

<Example 73>
<Synthesis of 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -3-methylpiperazine (3-28)>
1- (4-Chlorobenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -2-methylpiperazine (1.22 g, 2.73 mmol) To a dichloromethane solution (9 ml) was added 1-chloroethyl chloroformate (430 mg, 3.01 mmol) at room temperature, and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, methanol (9 ml) was poured, and the mixture was heated to reflux for 8.5 hours. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: methanol / chloroform = 1/7) to give the title compound as a brown oil (yield 290 mg, yield 33%).

<Example 74>
Synthesis of <1- (4-chlorobenzyl) -4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -2-methylpiperazine (3-51) ( Diastereomer ratio about 3: 1 mixture))
N ′-(2-chloro-1-methylethyl) -N ′-(4-chlorobenzyl) -N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl A solution of ethane-1,2-diamine (0.4 g, 8.28 mmol) in N-methyl-2-pyrrolidinone (3 ml) was stirred at 180 ° C. for 1.5 hours. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/7) to give the title compound (yield 250 mg, 68%) as a yellow oil.

<Example 75>
Synthesis of <1- (4-chlorobenzyl) -2-cyclopropyl-4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (3-89) >
N ′-(4-Chlorobenzyl) -N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] ethane-1,2-diamine (500 mg, 1.23 mmol) ) In 1,2-dichloroethane (6 ml), sodium triacetoxyborohydride (260 mg, 1.23 mmol), 2-bromo-1-cyclopropylethanone (190 mg, 1.17 mmol) and acetic acid (75 mg, 1. 23 mmol) was added at room temperature, and the mixture was stirred at the same temperature for 3 hours and at 50 ° C. for 6.5 hours. A 1N aqueous sodium hydroxide solution was poured into the reaction mixture, and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound (yield 41.7 mg, yield 6.7%) as a yellow oil.

<Example 76>
<Synthesis of 4- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] -3-methyl-piperazin-2-one (3-261)>
2-Bromo-N- (2-{[2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] amino} ethyl) propanamide (2.00 g, 4.79 mmol) Of N-methyl-2-pyrrolidinone (2.4 ml) was stirred at 170 ° C. for 1 hour. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 3/1) to give the title compound (yield 0.56 g, yield 35%) as a yellow oil.

Tables 4-1 to 4-26 show the ¹ HNMR spectrum (CDCl ₃ ) σ (ppm) value, melting point (° C.) and the like of the compounds according to the present invention prepared according to the examples and the examples. ¹ HNMR data was measured with a JNM-ECS400 spectrometer (manufactured by JEOL Ltd.), and in Tables 4-1 to 4-26, σ values were displayed in ppm.

  Hereinafter, Reference Examples 1 to 6 show synthesis examples in which the starting materials of the compounds according to the present invention produced according to the examples and the examples are synthesized from commercially available products. For example, 1- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] piperazine (1-276) of Example 71 is similar to 2-fluoro-4- 2-Fluoro-4-methyl-5-[(2,2,2-tri) synthesized using 5-amino-4-fluoro-2-methylbenzenethiol synthesized from methylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) Fluoroethyl) thio] aniline as a starting material.

<Reference Example 1>
<N '-(2-chloro-1-methylethyl) -N'-(4-chlorobenzyl) -N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) Synthesis of phenyl] ethane-1,2-diamine (diastereo ratio of about 3: 1 mixture)>
N ′-(4-Chlorobenzyl) -N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] ethane-1,2-diamine (2.38 g, 5 .85 mmol) in 1,2-dichloroethane (29 ml), sodium triacetoxyborohydride (1.24 g, 5.85 mmol), chloroacetone (0.51 g, 5.56 mmol) and acetic acid (0.35 g, 5. 85 mmol) was added at 0 ° C. and stirred at room temperature for 10 hours. A 1N aqueous sodium hydroxide solution was poured into the reaction mixture, and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/7) to give the title compound (yield 0.94 g, yield 33%) as a yellow oil.
¹ HNMR spectrum (CDCl ₃ ) σ: 7.19-7.27 (4H, m), 6.83 (0.75H, d, J = 12.1 Hz), 6.82 (0.25H, d, J) = 12.1 Hz), 6.74 (0.75 H, d, J = 8.7 Hz), 6.70 (0.25 H, d, J = 8.7 Hz), 4.25 (1 H, br)
s), 3.99-4.07 (0.75H, m), 3.38-3.72 (2.25H, m), 3.23 (2H, q, J = 9.8 Hz), 2. 99-3.12 (2.25H, m), 2.63-2.84 (3.75H, m), 2.35 (2.25H, s), 2.35 (0.75H, s), 1.45 (2.25H, d, J = 6.4 Hz), 1.12 (0.75H, d, J = 6.4 Hz).

<Reference Example 2>
<Synthesis of N '-(4-chlorobenzyl) -N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] ethane-1,2-diamine>
To a dichloromethane solution (21 ml) of N- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] ethane-1,2-diamine (1.9 g, 6.74 mmol) Sodium triacetoxyborohydride (1.43 g, 6.74 mmol), 4-chlorobenzaldehyde (0.85 g, 6.06 mmol) and acetic acid (0.4 g, 6.74 mmol) were added at 0 ° C. and 1 at room temperature. Stir for hours. A 10% aqueous sodium hydroxide solution was poured into the reaction mixture, and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/1) to give the title compound (yield 1.1 g, 40%) as a pale yellow oil.
¹ HNMR spectrum (CDCl ₃ ) σ: 7.23-7.83 (4H, m), 6.86 (1H, d, J = 8.5 Hz), 6.84 (1H, d, J = 10.5 Hz) ), 4.25 (1H, br
s), 3.77 (2H, s), 3.26 (2H, q, J = 9.9 Hz), 3.19 (2H, t, J = 5.5 Hz), 2.89 (2H, t, J = 5.5 Hz), 2.35 (3H, s).

<Reference Example 3>
<Synthesis of 2-bromo-N- (2-{[2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] amino} ethyl) propanamide>
Triethylamine in a chloroform solution (5.0 ml) of 2-{[2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] amino} ethylamine hydrochloride (160 mg, 0.502 mmol) (152 mg, 1.51 mmol) and 2-bromopropionyl bromide (108 mg, 0.502 mmol) were added at 0 ° C. and stirred at the same temperature for 30 minutes. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 2/5) to give the title compound as white crystals (yield 180 mg, 86%).
¹ HNMR spectrum (CDCl ₃ ) σ: 6.89 (1H, d, J = 8.7 Hz), 6.83 (1H, bs), 6.83 (1H, d, J = 11.9 Hz), 4. 40 (1H, q, J = 7.7 Hz), 3.51 (2H, q, J = 6.1 Hz), 3.31 (2H, t, J = 6.0 Hz), 3.30 (2H, q , J = 9.8 Hz), 2.33 (3H, s), 1.84 (3H, d, J = 6.9 Hz).

<Reference Example 4>
<Synthesis of 2-{[2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenyl] amino} ethylamine hydrochloride>
2-Oxazolidinone (1) was added to a solution of 2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) aniline hydrochloride (6.30 g, 22.85 mmol) in diethylene glycol monomethyl ether (4.6 ml). .99 g, 22.85 mmol) was added and stirred at 170 ° C. for 10 hours. The precipitated crystals were washed with acetone to obtain the title compound (yield 4.77 g, yield 66%) as white crystals.
¹ HNMR spectrum (DMSO-d6) σ: 8.07 (2H, bs), 6.95 (1H, d, J = 12.8 Hz), 6.90 (1H, d, J = 8.7 Hz), 5 .60 (1H, t, J = 5.7 Hz), 3.82 (2H, q, J = 10.5 Hz), 3.32 (2H, t, J = 6.2 Hz), 2.92 (2H, t, J = 6.2 Hz), 2.22 (3H, s).

<Reference Example 5>
<Synthesis of 2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) aniline>
To a solution of 5-amino-4-fluoro-2-methylbenzenethiol (950 mg, 6.04 mmol) in N, N-dimethylformamide (5 ml) was added potassium carbonate (1.00 g, 7.24 mmol) and 2,2,2- Trifluoro-1-iodoethane (1.27 g, 6.05 mmol) was added at room temperature and stirred at the same temperature for 4 hours. Water was poured into the reaction mixture and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound (yield 1.16 g, yield 80%) as a yellow oil.
¹ HNMR spectrum (CDCl ₃ ) σ: 6.98 (1H, d, J = 9.0 Hz), 6.86 (1H, d, J = 10.4 Hz), 3.63 (2H, br.s), 3.28 (2H, q, J = 9.9 Hz), 2.36 (3H, s).

The following compounds were synthesized according to the method of Reference Example 5.
2-Fluoro-4-methyl-5- (methylthio) aniline
¹ HNMR spectrum (CDCl ₃ ) σ: 6.79 (1H, d, J = 12.0 Hz), 6.63 (1H, d, J = 8.8 Hz), 3.61 (2H, br.s), 2.37 (3H, s), 2.22 (3H, s).
2-Fluoro-4-methyl-5- (allylthio) aniline
¹ HNMR spectrum (CDCl ₃ ) σ: 6.80 (2H, t, J = 10.1 Hz), 6.64-6.74 (1H, m), 5.79-5.89 (2H, m), 3.57 (2H, br.s), 3.41 (2H, d, J = 7.3 Hz), 2.28 (3H, s).
2-Fluoro-4-methyl-5-[(propyn-2-yl) thio] aniline
¹ HNMR spectrum (CDCl ₃ ) σ: 6.94 (1H, d, J = 9.2 Hz), 6.84 (1H, d, J = 11.9 Hz), 3.61 (2H, br.s), 3.47 (2H, d, J = 2.7 Hz), 2.31 (3H, s), 2.20 (1H, t, J = 2.7 Hz).
2-Fluoro-4-methyl-5-[(cyanomethyl) thio] aniline
¹ HNMR spectrum (CDCl ₃ ) σ: 7.03 (1H, d, J = 8.8 Hz), 6.90 (1H, d, J = 11.6 Hz), 3.71 (2H, br.s), 3.43 (2H, s), 2.38 (3H, s).
3- (2,2,2-trifluoroethylthio) aniline
¹ HNMR spectrum (CDCl ₃ ) σ: 7.10 (1H, t, J = 8.1 Hz), 6.85 (1H, d, J = 8.1 Hz), 6.79 (1H, s), 6. 59 (1H, d, J = 8.1 Hz), 3.70 (2H, br.s), 3.43 (2H, q, J = 9.3 Hz).
2-Chloro-5- (2,2,2-trifluoroethylthio) aniline
¹ HNMR spectrum (CDCl ₃ ) σ: 7.19 (1H, d, J = 8.8 Hz), 6.89 (1H, s), 6.79 (1H, d, J = 8.8 Hz), 4. 08 (2H, br.s), 3.40 (2H, q, J = 9.6 Hz).
2,4-Dimethyl-5- (2,2,2-trifluoroethylthio) aniline
¹ HNMR spectrum (CDCl ₃ ) σ: 6.91 (1H, s), 6.84 (1H, s), 3.52 (2H, br.s), 3.31 (2H, q, J = 9. 6 Hz), 2.34 (3H, s), 2.13 (3H, s).
4-Methyl-5- (2,2,2-trifluoroethylthio) aniline
¹ HNMR spectrum (CDCl ₃ ) σ: 7.00 (1H, d, J = 8.4 Hz), 6.82 (1H, s), 6.56 (1H, d, J = 8.4 Hz), 3. 59 (2H, br.s), 3.37 (2H, q, J = 10.0 Hz), 2.40 (3H, s).
2-Fluoro-4-methyl-5- (cyclopropylmethylthio) aniline
¹ HNMR spectrum (CDCl ₃ ) σ: 6.83 (1H, d, J = 8.4 Hz), 6.81 (1H, d, J = 12.4 Hz), 2.71 (2H, d, J = 6) .8 Hz), 2.30 (3H, s), 1.58 (2H, br.s), 1.02-0.98 (1H, m), 0.58-0.53 (2H, m), 0.23-0.19 (2H, m).
2,4-difluoro-5- (2,2,2-trifluoroethylthio) aniline
¹ HNMR spectrum (CDCl ₃ ) σ: 6.92 (1H, dd, J = 9.4, 7.1 Hz), 6.80 (1H, dd, J = 10.5, 8.7 Hz), 3.65 (2H, br), 3.33 (2H, q, J = 9.8 Hz).
2-Fluoro-4-methyl-5- (isobutylthio) aniline
¹ HNMR spectrum (CDCl ₃ ) σ: 6.80 (1H, d, J = 11.4 Hz), 6.76 (1H, d, J = 9.2 Hz), 3.59 (2H, br), 2. 67 (2H, d, J = 6.9 Hz), 2.28 (3H, s), 1.86-1.76 (1 H, m), 1.02 (6H, d, J = 6.9 Hz).
2-Fluoro-4-methyl-5- (3,3,3-trifluoropropylthio) aniline
¹ HNMR spectrum (CDCl ₃ ) σ: 6.89 (1H, d, J = 11.6 Hz), 6.82 (1H, d, J = 8.8 Hz), 3.64 (2H, br.s), 2.93-2.89 (2H, m), 2.39-2.27 (5H, m).
2-Fluoro-4-methyl-5- (pentafluoroethylthio) aniline
¹ HNMR spectrum (CDCl ₃ ) σ: 6.08 (1H, d, J = 8.4z), 6.96 (1H, d, J = 11.6 Hz), 3.70 (2H, br.s), 2.40 (3H, s).

<Reference Example 6>
<Synthesis of 5-amino-4-fluoro-2-methylbenzenethiol>
Acetyl chloride (17.4 g, 222 mmol) was added to a dichloromethane solution (200 ml) of 2-fluoro-4-methylaniline (25.3 g, 202 mmol) (manufactured by Tokyo Chemical Industry Co., Ltd.) and triethylamine (30.7 g, 304 mmol). The mixture was added at ° C and stirred at room temperature for 4 hours. Water was poured into the reaction mixture and extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was washed with n-hexane to obtain white crystals (yield 28.0 g, yield 83%). The obtained crystals were added to chlorosulfonic acid (58.0 g, 498 mmol) at 0 ° C. and stirred at 80 ° C. for 2 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was washed with diisopropyl ether to obtain white crystals (yield 19.3 g, yield 43%). Red phosphorus (7.87 g, 254 mmol) and iodine (921 mg, 3.63 mmol) were added to an acetic acid solution (80 ml) of the obtained crystals at room temperature, and the mixture was heated to reflux for 2 hours. Ice water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was washed with n-hexane to obtain white crystals (yield 16.3 g, yield 93%). The obtained crystals were added to 10% sodium hydroxide solution (400 ml) and heated to reflux for 3 hours. Dilute hydrochloric acid was added to the reaction mixture to adjust to pH 7 and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3) to give the title compound as white crystals (yield 8.50 g, yield 80%).
¹ HNMR spectrum (CDCl ₃ ) σ: 6.80 (1H, d, J = 12.0 Hz), 6.75 (1H, d, J = 8.4 Hz), 3.57 (2H, br.s), 3.14 (1H, br.s), 2.22 (3H, s).

The following compounds were synthesized according to the method of Reference Example 6.
5-Amino-4-chlorobenzenethiol MS (EI): 159 (M ⁺ )
5-Amino-2,4-dimethylbenzenethiol MS (EI): 153 (M ⁺ )
5-amino-2-methylbenzenethiol
¹ HNMR spectrum (CDCl ₃ ) σ: 6.92 (1H, d, J = 8.4 Hz), 6.64 (1H, s), 6.43 (1H, d, J = 8.4 Hz), 3. 60 (2H, br.s), 3.19 (1H, br.s), 2.21 (3H, s).
5-amino-2,4-difluorobenzenethiol
¹ HNMR spectrum (CDCl ₃ ) σ: 6.77 (1H, dd, J = 10.5, 8.7 Hz), 6.66 (1H, dd, J = 8.2, 8.2 Hz), 3.52 (3H, br).

2. Formulation Examples Formulation production examples of pest control agents using compounds synthesized according to Examples 1 to 76 and the above examples are shown below. In addition, an additive and addition amount are not limited to the following manufacture example, It can prepare suitably.

(1) Preparation of powder A uniform mixture of the compound synthesized in Example 1 (2 parts by mass), PAP (isopropyl phosphate ester) (physical modifier) (1 part by mass) and Cree (97 parts by mass) To obtain a powder containing 2% by mass of the compound synthesized in Example 1.
Moreover, also when the compound synthesize | combined according to Example 2- Example 76 and the said Example was used, the powder agent was obtained by the same method.

(2) Preparation of wettable powder of the compound synthesized in Example 1 (20 parts by mass), sodium alkylbenzenesulfonate (3 parts by mass), polyoxyethylene nonylphenyl ether (5 parts by mass) and clay (72 parts by mass) By uniformly mixing and grinding the mixture, a wettable powder containing 20% by mass of the compound synthesized in Example 1 was obtained.
Moreover, also when using the compound synthesize | combined according to Example 2- Example 76 and the said Example, the wettable powder was obtained by the same method.

(3) Preparation of Emulsion The compound synthesized in Example 1 (30 parts by mass), methyl ethyl ketone (40 parts by mass) and polyoxyethylene nonylphenyl ether (30 parts by mass) were mixed and dissolved, and synthesized according to Example 1. An emulsion containing 30% by mass of the obtained compound was obtained.
Further, when the compounds synthesized according to Examples 2 to 76 and the above examples were used, emulsions were obtained in the same manner.

(4) Preparation of flowable agent:
Of the compound synthesized in Example 1 (25 parts by mass), polyoxyethylene alkyl ether (1 part by mass), sodium alkylnaphthalene sulfonate (1 part by mass), carboxymethylcellulose (1 part by mass) and water (72 parts by mass) By mixing the mixture uniformly, a flowable agent containing 25% by mass of the compound synthesized in Example 1 was obtained.
Moreover, also when using the compound synthesize | combined according to Example 2- Example 76 and the said Example, the flowable agent was obtained by the same method.

(5) Preparation of granules:
To a mixture of the compound synthesized in Example 1 (5 parts by mass), sodium lauryl sulfate (1 part by mass), calcium lignin sulfonate (5 parts by mass), bentonite (30 parts by mass) and clay (59 parts by mass), After adding water (15 parts by mass) and kneading with a kneader, the mixture was granulated with a granulator and dried with a fluid dryer to obtain a granule containing 5% by mass of the compound synthesized in Example 1. .
Moreover, also when using the compound synthesize | combined according to Example 2- Example 76 and the said Example, the granule was obtained by the same method.

3. Evaluation of control effect on pests The control effect was evaluated using the pest control agent according to the present invention obtained as described above.

(1) Control test against Spodoptera litura Cabbage leaf pieces (diameter 8 cm) were immersed in an emulsion diluent (500 ppm) prepared according to Formulation Example (3) and then air-dried. The leaf pieces were placed in a plastic petri dish with filter paper, 10 second-instar larvae of Spodoptera litura were released, covered with small holes, and placed in a constant temperature room at 25 ° C. Six days after the release, the number of surviving insects was examined, and the death rate (%) was calculated using the formula 1 to evaluate the control properties. The test was carried out in two consecutive systems.

  As representative examples, the compounds Nos. 1-528, 1-664, 1-694, 1-705, 1-770, 1-898, 1-1023, 1-1025, and 1-1347 have a death rate of 90%. The above is shown.

  On the other hand, the compound (N- {4- [4- (2-fluorophenyl) piperazin-1-ylmethyl] benzyl} described in Patent Document 1 (Patent Document WO99 / 019301) represented by the following formula (48): Acetamide) and a commercially available compound represented by formula (49) (Zelinsky Institute Inc.) (1- (4-chlorobenzoyl) -4- (2-fluorophenyl) piperazine) (hereinafter referred to as comparative compound (48), comparative compound ( 49).) Was subjected to a test under the same conditions as in the above test example, and the controllability was evaluated. The death rate of the compound of the comparative compound (48) and the comparative compound (49) was 30% or less.

(2) Control test against brown planthopper Rice seedling seedlings cultivated in a plastic cup were placed on a turntable, and an emulsion diluted solution (500 ppm) prepared according to Formulation Example (3) was sprayed uniformly with a spray gun. After air-drying, it was placed in a polycarbonate plastic container with a nylon gorge on the lid, and 10 4th instar larvae were released, and placed in a constant temperature room at 25 ° C. Seven days after the release, the number of surviving insects was examined, and the death rate (%) was calculated using the formula 1 to evaluate the control properties. The test was carried out in two consecutive systems.

  As representative examples, the compounds Nos. 1-9, 1-27, 1-306, 1-666, 1-907, 2-15, 3-15 showed a death rate of 90% or more.

  On the other hand, the comparative compound (48) and the comparative compound (49) were subjected to a test under the same conditions as in the above test example to evaluate the control property. The death rate of the compound of the comparative compound (48) and the comparative compound (49) was less than 60%.

(3) Control test against bean aphids Three pealess aphids were released on each broad bean seedling cultivated in a plastic cup. One day after the release, this broad bean seedling was placed on a turntable, and an emulsion diluted solution (500 ppm) prepared according to Formulation Example (3) was sprayed uniformly with a spray gun. After the treatment, it was placed in a constant temperature room at 25 ° C. (16 hours illumination), the number of live insects parasitized 4 days after the treatment was examined, and the control value (%) was calculated by the formula of Formula 2 to evaluate the control property. The test was carried out in two consecutive systems.

  As representative examples, the compound numbers 1-225, 1-321, 1-371, 1-403, 1-601, 1-772, 1-794, 1-821, 1-1170, 1-1287, 2-101 3-15 showed a control value of 80% or more.

  On the other hand, the comparative compound (48) and the comparative compound (49) were subjected to a test under the same conditions as in the above test example to evaluate the control property. The control value of the compound of the comparative compound (48) and the comparative compound (49) was less than 20%.

(4) Control test against a spider mite Ten adult spider mites were released on each green seedling cultivated in a plastic cup. One day after the release, the green seedlings were placed on a turntable, and an emulsion diluted solution (100 ppm) prepared according to Formulation Example (3) was sprayed uniformly with a spray gun. After the treatment, it was placed in a constant temperature room at 25 ° C. (16 hours illumination), the number of live insects parasitized 8 days after the treatment was examined, and the control value (%) was calculated by the formula 2 to evaluate the control property. The test was carried out in two consecutive systems.

  As representative examples, the compound numbers 1-48, 1-133, 1-201, 1-207, 1-217, 1-218, 1-221, 1-222, 1-223, 1-225, 1-241 are shown. 1-246, 1-250, 1-252, 1-254, 1-256, 1-260, 1-276, 1-278, 1-279, 1-280, 1-283, 1-284, 1 -288, 1-291, 1-301, 1-303, 1-306, 1-307, 1-308, 1-315, 1-318, 1-319, 1-321, 1-324, 1-326 1-331, 1-332, 1-333, 1-339, 1-340, 1-348, 1-349, 1-352, 1-353, 1-356, 1-362, 1-366, 1 -367, 1-368, 1-369, 1-371, 1-373, 1- 77, 1-379, 1-381, 1-383, 1-385, 1-387, 1-388, 1-391, 1-392, 1-393, 1-395, 1-397, 1-398, 1-399, 1-401, 1-403, 1-404, 1-407, 1-412, 1-415, 1-418, 1-419, 1-420, 1-421, 1-423, 1- 425, 1-427, 1-428, 1-429, 1-431, 1-433, 1-436, 1-437, 1-439, 1-442, 1-443, 1-444, 1-446, 1-447, 1-44481-449, 1-450, 1-453, 1-456, 1-457, 1-458, 1-459, 1-460, 1-463, 1-472, 1-473, 1-474, 1-476, 1-478, 1-484, 1-485, -486, 1-487, 1-491, 1-493, 1-500, 1-501, 1-502, 1-504, 1-507, 1-509, 1-510, 1-518, 1-521 1-523, 1-525, 1-527, 1-528, 1-530, 1-532, 1-534, 1-536, 1-537, 1-539, 1-540, 1-541, 1 -542, 1-543, 1-544, 1-545, 1-546, 1-547, 1-549, 1-550, 1-551, 1-552, 1-554, 1-555, 1-556 1-558, 1-560, 1-561, 1-563, 1-564, 1-565, 1-567, 1-569, 1-571, 1-573, 1-575, 1-577, 1 -579, 1-580, 1-581, 1-582, 1-583, 1-58 4, 1-586, 1-587, 1-589, 1-590, 1-593, 1-594, 1-595, 1-597, 1-600, 1-601, 1-606, 1-607, 1-608, 1-609, 1-610, 1-611, 1-613, 1-614, 1-616, 1-618, 1-619, 1-620, 1-621, 1-623, 1- 624, 1-626, 1-628, 1-629, 1-631, 1-632, 1-635, 1-636, 1-641, 1-644, 1-652, 1-653, 1-657, 1-661, 1-663, 1-664, 1-666, 1-667, 1-668, 1-669, 1-670, 1-670, 1-674, 1-680, 1-683, 1- 685, 1-689, 1-690, 1-693, 1-694, 1-695, 1 696, 1-697, 1-698, 1-699, 1-702, 1-703, 1-704, 1-705, 1-708, 1-709, 1-710, 1-714, 1-714, 1-719, 1-722, 1-726, 1-727, 1-728, 1-732, 1-737, 1-738, 1-740, 1-741, 1-743, 1-745, 1- 756, 1-747, 1-749, 1-754, 1-763, 1-764, 1-765, 1-766, 1-767, 1-768, 1-770, 1-772, 1-774, 1-776, 1-778, 1-781, 1-794, 1-797, 1-798, 1-799, 1-800, 1-807, 1-810, 1-812, 1-814, 1- 816, 1-818, 1-821, 1-823, 1-824, 1-82 1-827, 1-828, 1-829, 1-830, 1-831, 1-832, 1-837, 1-838, 1-840, 1-858, 1-864, 1-866, 1 -868, 1-870, 1-872, 1-873, 1-876, 1-878, 1-880, 1-882, 1-888, 1-890, 1-891, 1-892, 1-893 1-894, 1-896, 1-898, 1-900, 1-901, 1-902, 1-903, 1-905, 1-907, 1-908, 1-909, 1-922, 1 -925, 1-948, 1-950, 1-952, 1-954, 1-956, 1-958, 1-960, 1-964, 1-965, 1-967, 1-968, 1-989 1-991, 1-998, 1-1001, 1-1005, 1-1007 1-1009, 1-1011, 1-1013, 1-1017, 1-1018, 1-1020, 1-1021, 1-1023, 1-1025, 1-1027, 1-1031, 1-1058, 1 -1097, 1-1127, 1-1128, 1-1129, 1-1131, 1-1142, 1-1145, 1-11161, 1-1164, 1-1167, 1-1170, 1-1187, 1-1197 1-1223, 1-1266, 1-1287, 1-1314, 1-1332, 1-1340, 1-1343, 1-1347, 2-62, 2-66, 2-70, 2-75, 2 -88, 2-115, 2-142, 2-218, 2-225, 2-238, 2-242, 2-246, 2-248, 2-297, 2-320, 2-327, 2-332 , 2-33 2-341, 2-345, 2-347, 2-367, 2-368, 2-371, 399, 3-1, 3-15, 3-28, 3-36, 3-47, 3 The compounds of −51, 3-89, and 3-261 showed a control value of 80% or more.

  On the other hand, the comparative compound (48) and the comparative compound (49) were subjected to a test under the same conditions as in the above test example to evaluate the control property. The control value of the compound of the comparative compound (48) and the comparative compound (49) was less than 30%.

  From the above results, it was confirmed that the pesticidal agent according to the present invention exhibited an excellent controlling effect as compared with the comparative compound in any of the above-mentioned pests and was useful as a pesticidal agent.

  Since the substituted phenyl piperazine compound or a salt thereof according to the present invention has an excellent control effect against pests, the pests can be controlled effectively if used as a pest control agent.

Claims (5)

The substituted phenyl piperazine compound or its salt represented by following formula (1).

In the formula, A, one or more may be substituted with _{G 1 C} 1 _{-C 20} alkyl group, one or more may be substituted with _{G 1 C} 2 _{-C 20} alkenyl group, one or more optionally substituted _C 2 be _{-C 20} alkynyl group G _1, one or more may be substituted with _{G 1 C} 3 _{-C 20} cycloalkyl group which may be substituted by one or more _{G 1} C ₃ -C ₂₀ cycloalkenyl group, one or more may be substituted with _{G 1 C} 1 _{-C 20} haloalkyl group, one or more may be substituted with _{G 1 C} 2 _{-C 20} haloalkenyl group or, be substituted with one or more in _{G 1} represents an optionally _C 2 _{-C 20} haloalkynyl group,
G ₁ is a cyano group, a cycloalkyl group, an alkoxy group, an alkylthio group, an alkylamino group, a dialkylamino group, an alkoxycarbonyl group, an aryl group optionally substituted with one or more G ₅ , or one or more G ₅ represents a heterocyclic ring which may be substituted with ₅ ,
R may be a hydrogen atom, a cyano group, a formyl group, a halocarbonyl group, a thioformyl group, a C ₁ -C ₂₀ alkyl group that may be substituted with one or more G ₂ , and may be substituted with one or more G _2. good _C 2 _{-C 20} alkenyl group, one or more optionally substituted with _{G 2 C 2 ~C 20} alkynyl group, one or more optionally substituted with _{G 3 C 3 ~C 20} cycloalkyl group, C ₁ -C ₂₀ cycloalkenyl group optionally substituted with one or more G ₃ , C ₁ -C ₂₀ alkylcarbonyl group optionally substituted with one or more G ₂ , substituted with one or more G ₂ which may be _C 1 _{-C 20} alkyl thio group, one or more optionally substituted with _{G 2 C} 2 _{-C 20} alkenylcarbonyl group, one or more substituted with _{G 2} good _C 2 be -C ₂₀ alkenylene thiocarbonyl One or more optionally substituted with _{G 2 C 2 ~C 20} alkynyl group, one or more optionally substituted with _{G 3 C 3 ~C 20} cycloalkyl group, one or more _{G 3} in optionally substituted _C 3 _{-C 20} cycloalkylthio group, one or more may be substituted by _{G 3 C 3 ~C 20} cycloalkyl group may be substituted by one or more _{G 2} C ₁ -C ₂₀ alkoxycarbonyl group, one or more _{G 2} substituted by _C 1 may be _{-C 20} alkoxy thiocarbonyl group, one or more _C 1 may be substituted by _{G 2 -C 20} alkylamino carbonyl group, one or more substituted with _{G 2 C} 1 _{-C 20} may be alkylaminothiocarbonyl group, one or more _di-C 2 may be substituted with _{G 2} of _{-C 20} alkylamino Carbonyl group, one or more _di-C 2 may be substituted with _{G 2} of _{-C 20} alkylamino thiocarbonyl group, one or more optionally substituted with _{G 3 C 3 ~C 20} cycloalkyl amino carbonyl group, hydroxyl group, one or more optionally substituted with _{G 2 C} 1 _{-C 20} alkoxy group, one or more optionally substituted with _{G 2 C} 1 _{-C 20} alkylamino group, one or more _{G 2} in optionally substituted di _C 2 _{-C 20} alkylamino group, halosulfonyl group, one or more optionally substituted with _{G 2 C} 1 _{-C 20} alkylsulfonyl group, substituted by one or more _{G 2} which may be _C 2 _{-C 20} alkenyl-sulfonyl group, one or more optionally substituted with _{G 3 C 3 ~C 20} cycloalkyl sulfonyl group, one or more substituted with _{G 2} good _C 1 be -C ₂₀ Archi Le aminosulfonyl group, one or more G ₂ that is substituted di C ₂ may be -C ₂₀ alkyl aminosulfonyl group, one or more di-C ₄ may be substituted by G ₂ -C ₂₀ alkenyl aminosulfonyl group one or more _di-C 4 may be substituted by _{G 2 -C 20} alkynyl aminosulfonyl group, one or more substituted with _{G 3} di _C 6 which may be _{-C 20} cycloalkyl aminosulfonyl group, one more G ₂ substituted by tri C ₃ -C ₂₀ optionally alkylsilyl group, one or more G ₃ which may be substituted with a benzyl group, one or more G ₃ which may be substituted with an aryl group , one or more G ₃ which may be substituted with a heterocyclic carbonyl group, one or more substituted with G ₃ which may be arylthiocarbonyl group, one or more substituted with G ₃ heterocyclic ring which may Chiokarubo Group, one or more G ₃ which may be substituted with arylcarbonyl group, one or more G ₃ which may be substituted with an aryloxycarbonyl group, one or more substituted with G ₃ may be complex ring oxycarbonyl group, one or more substituted with G ₃ may be aryloxythiocarbonyl group, one or more may be substituted by G ₃ heterocyclyloxy thiocarbonyl group, substituted with one or more G ₃ It is aryl aminocarbonyl group optionally one or more G ₃ which may be substituted with a heterocyclic aminocarbonyl group, one or more G ₃ which may be substituted with arylaminothiocarbonyl group, one or more G ₃ which may be substituted with a heterocyclic amino thiocarbonyl group, one or more substituted with G ₃ arylsulfonyl group which may include one or more heterocyclic sulfonyl which may be substituted with G ₃ Group, one or more may be substituted by G ₃ arylaminosulfonyl group, one or more G ₃ may be substituted by a heterocyclic aminosulfonyl group, it may be substituted with one or more G ₃ An aryl group, or a heterocycle optionally substituted with one or more G ₃ ;
G ₂ is a halogen atom, cyano group, cycloalkyl group, alkoxy group, alkylthio group, alkylamino group, dialkylamino group, alkylsulfinyl group, alkylcarbonyl group, cycloalkylcarbonyl group, alkoxycarbonyl group, alkoxyimino group, alkenyl oximino group, alkynyloxy imino group, halo alkoxyiminoalkyl group, one or more G ₅ with an optionally substituted aryl group, one or more heterocyclic ring which may be substituted with G _5, one or more G ₅ in unsubstituted or substituted aryl carbonyl group, one or more G ₅ which may be substituted with a heterocyclic carbonyl group or one or more optionally substituted aryloxy group G _5,,
G ₃ is a halogen atom, cyano group, nitro group, alkyl group, alkenyl group, alkynyl group, haloalkyl group, cycloalkyl group, alkoxy group, haloalkoxy group, alkylthio group, haloalkylthio group, alkylsulfinyl group, haloalkylsulfinyl group Alkylsulfonyl group, haloalkylsulfonyl group, alkylamino group, dialkylamino group, alkenylamino group, alkynylamino group, alkylcarbonyl group, alkoxycarbonyl group, alkylaminocarbonyl group, haloalkylaminocarbonyl group, alkylcarbonylaminoalkyl group, 1 one or more G ₅ with an optionally substituted aryl group, one or more G ₅ with an optionally substituted aryloxy group, one or more G ₅ with an optionally substituted benzyl group, one or more G ₅ with a substituent Which may be a benzoyl group, one or more G ₅ heterocyclic ring which may be substituted by or one or more may be substituted by G ₅ heterocyclic oxy group,
G ₅ is a halogen atom, cyano group, nitro group, alkyl group, alkenyl group, alkynyl group, haloalkyl group, cycloalkyl group, alkoxy group, haloalkoxy group, alkylthio group, haloalkylthio group, alkylamino group, dialkylamino group Represents a haloalkylamino group,
X is a halogen atom, a cyano group, substituted nitro group, a substituted C ₁ may be -C ₆ alkyl group by a halogen atom, a substituted C ₁ may be -C ₆ alkoxy group with a halogen atom or a halogen atom, shows good _C 1 -C ₆ alkylthio group, a
Y is a halogen atom, an oxygen atom, a sulfur atom, one or more may be substituted by _{G 4 C} 1 -C ₆ alkyl group, one or more may be substituted by _{G 4 C} 1 -C ₆ haloalkyl group, one or more may be substituted by _{G 4 C} 3 _{~C 6} cycloalkyl group, or one or more may be substituted by _{G 4 C} 1 -C ₆ alkoxy group.
However, two Y on the same carbon can also represent (= O) or (= S), and can also form (C = O) or (C = S). Two Ys may be bonded to each other to represent a carbocyclic or heterocyclic ring. Y may be the same or different.
G ₄ represents a cyano group, an alkoxy group, an alkylthio group, an alkylamino group, a dialkylamino group, or an alkoxycarbonyl group,
m represents an integer of 0 to 4,
n represents an integer of 0 to 8,
p represents an integer of 0 to 2,
q and r each represent an integer of 0 to 1) Wherein A is one or more of which can be substituted by _{G 1 C} 1 _{-C 10} alkyl group, one or more may be substituted with _{G 1 C} 2 _{-C 10} alkenyl group, one or more in _{G 1} in optionally substituted _C 2 _{-C 10} alkynyl group, one or more may be substituted with _{G 1 C} 3 _{-C 10} cycloalkyl group, one or more substituted with _{G 1} optionally _C 3 be ~ C ₅ cycloalkenyl group, one or more may be substituted with _{G 1 C} 1 _{-C 10} haloalkyl group, one or more may be substituted with _{G 1 C} 2 _{-C 10} haloalkenyl group or one, shows the above may be substituted with _{G 1 C} 2 _{~C 5} haloalkynyl group,
G ₁ is a cyano group, a C _{3 to} C ₆ cycloalkyl group, a C _{1 to} C ₆ alkoxy group, a C _{1 to} C ₆ alkylthio group, a C _{1 to} C ₆ alkylamino group, or a di C _{2 to} C ₆ alkylamino. group, C ₁ -C ₆ alkoxycarbonyl group, one or more G ₅ with an optionally substituted aryl group or at least one heterocyclic ring which may be substituted with G _5,,
Wherein R is a hydrogen atom, a cyano group, a formyl group, halocarbonyl group, thioformyl group, one or more optionally substituted with G ₂ C ₁ -C ₂₀ alkyl group, substituted with one or more G ₂ which may _C 2 _{-C 10} alkenyl group, one or more optionally substituted with _{G 2 C 2 ~C 10} alkynyl group, one or more optionally substituted with _{G 3 C 3 ~C 10} cycloalkyl group one or more optionally substituted with _{G 3 C 3 ~C 8} cycloalkenyl group, one or more optionally substituted with _{G 2 C} 1 _{-C 10} alkylcarbonyl group, at least one _{G 2} optionally substituted _C 1 _{-C 10} alkyl thio group, one or more optionally substituted with _{G 2 C} 2 _{-C 10} alkenylcarbonyl group, one or more substituted with _{G 2} good _C 2 be ~ C ₁₀ alkenylene Lucio carbonylation Group, one or more optionally substituted with _{G 2 C} 2 _{-C 10} alkynyl group, one or more optionally substituted with _{G 3 C} 3 _{-C 10} cycloalkyl group, one or more G ₃ optionally substituted _C 3 be _{-C 10} cycloalkylthio group, one or more optionally substituted with _{G 3 C} 3 _{-C 10} cycloalkenyl group, optionally substituted by one or more _{G 2} good _C 1 _{-C 10} alkoxycarbonyl group, one or more substituted with _{G 2 C} 1 may be _{-C 10} alkoxy thiocarbonyl group, one or more optionally substituted with _{G 2 C} 1 _{-C 10} alkyl aminocarbonyl group, one or more substituted with _{G 2 C} 1 may be _{-C 10} alkylamino thiocarbonyl group, one or more _di-C 2 may be substituted with _{G 2} of _{-C 10} alkylamino Carbonyl group, one or more _di-C 2 may be substituted with _{G 2} of _{-C 10} alkylamino thiocarbonyl group, one or more optionally substituted with _{G 3 C 3 ~C 10} cycloalkyl amino carbonyl group, hydroxyl group, one or more optionally substituted with _{G 2 C} 1 _{-C 10} alkoxy group, one or more optionally substituted with _{G 2 C} 1 _{-C 10} alkylamino group, one or more _{G 2} in optionally substituted di _C 2 _{-C 10} alkylamino group, halosulfonyl group, one or more optionally substituted with _{G 2 C} 1 _{-C 10} alkylsulfonyl group, substituted by one or more _{G 2} good _C 2 _{-C 10} alkenylsulfonyl group optionally one or more _{G 3} that is substituted may be _C 3 _{-C 10} cycloalkyl sulfonyl group, one or more substituted with _{G 2} good _C 1 be -C ₁₀ Al Kill aminosulfonyl group, one or more G ₂ substituted by di-C ₂ may be -C ₁₀ alkyl aminosulfonyl group, one or more di-C ₄ may be substituted by G ₂ -C ₁₀ alkenyl aminosulfonyl group one or more _di-C 4 may be substituted by _{G 2 -C 10} alkynyl aminosulfonyl group, one or more _di-C 6 optionally substituted by _{G 3} of _{-C 10} cycloalkyl aminosulfonyl group, one more G ₂ substituted by an optionally tri C ₃ -C ₁₀ alkylsilyl group, one or more G ₃ which may be substituted with a benzyl group, one or more G ₃ which may be substituted with an aryl group , one or more G ₃ which may be substituted with a heterocyclic carbonyl group, one or more substituted with G ₃ which may be arylthiocarbonyl group, one or more substituted with G ₃ heterocyclic ring which may Chiokaru Boniru group, one or more G ₃ which may be substituted with arylcarbonyl group, one or more G ₃ which may be substituted with an aryloxycarbonyl group, one or more substituted with G ₃ may be complex ring oxycarbonyl group, one or more substituted with G ₃ may be aryloxythiocarbonyl group, one or more may be substituted by G ₃ heterocyclyloxy thiocarbonyl group, substituted with one or more G ₃ It is aryl aminocarbonyl group optionally one or more G ₃ which may be substituted with a heterocyclic aminocarbonyl group, one or more G ₃ which may be substituted with arylaminothiocarbonyl group, one or more G ₃ which may be substituted with a heterocyclic amino thiocarbonyl group, one or more substituted with G ₃ arylsulfonyl group which may include one or more heterocyclic sul be substituted with G ₃ Group, one or more may be substituted by G ₃ arylaminosulfonyl group, one or more G ₃ may be substituted by a heterocyclic aminosulfonyl group, it may be substituted with one or more G ₃ An aryl group, or a heterocycle optionally substituted with one or more G ₃ ;
G ₂ is a halogen atom, a cyano group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkylamino group, or a di C ₂ -C. ₆ alkylamino _group, C 1 -C ₆ alkylsulfinyl _group, C 1 -C ₆ alkylcarbonyl _group, C 3 -C ₆ cycloalkyl _group, C 1 -C ₆ alkoxycarbonyl _group, C 1 -C ₆ alkoxyimino group A C ₂ -C ₆ alkenyloxyimino group, a C ₂ -C ₆ alkynyloxyimino group, a C ₁ -C ₆ haloalkoxyimino group, an aryl group optionally substituted by one or more G ₅ , one or more which may be heterocyclic substituted by G _5, one or more G ₅ which may be substituted with an arylcarbonyl group, one or more G ₅ which may be substituted with a heterocyclic carbonyl group, Other represents an aryloxy group which may be substituted by one or more G _5,
G ₃ is a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ haloalkyl group, or a C ₃ -C. ₆ cycloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ alkylsulfinyl group, C ₁ -C ₆ haloalkylsulfinyl _group, C 1 -C ₆ alkylsulfonyl _group, C 1 -C ₆ haloalkylsulfonyl _group, C 1 -C ₆ alkylamino group, _di-C 2 -C ₆ alkylamino _group, C 2 -C ₆ alkenyl amino _group, C 2 -C _{6 alkynylamino,} C 1 -C ₆ alkylcarbonyl _group, C 1 -C ₆ alkoxycarbonyl _group, C 1 -C ₆ alkylamino Carbonyl _group, C 1 -C ₆ haloalkylcarbonyl aminocarbonyl _group, C 2 -C ₆ alkylcarbonylamino group, one or more _{G 5} with an optionally substituted aryl group, optionally substituted by one or more _{G 5} an aryloxy group, one or more G ₅ with an optionally substituted benzyl group, one or more G ₅ with an optionally substituted benzoyl group, one or more heterocyclic ring which may be substituted with G _5, Or a heterocyclic oxy group optionally substituted with one or more G ₅ ;
G ₅ is a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C ₆ alkynyl group, a C ₁ -C ₆ haloalkyl group, or a C ₃ -C. ₆ cycloalkyl group, C ₁ -C ₆ alkoxy group, C ₁ -C ₆ haloalkoxy group, C ₁ -C ₆ alkylthio group, C ₁ -C ₆ haloalkylthio group, C ₁ -C ₆ alkylamino group, di-C ₂ -C ₆ alkylamino _group, a C 1 -C ₆ haloalkyl group,
Wherein X is a halogen atom, a cyano group, a nitro group, may be substituted with a halogen atom C ₁ -C ₆ alkyl group, optionally C ₁ -C ₆ alkoxy group optionally substituted by a halogen atom or substituted by a halogen atom, are also shown good _C 1 -C ₆ alkylthio group,
Wherein Y is a halogen atom, an oxygen atom, a sulfur atom, one or more may be substituted by _{G 4 C} 1 -C ₆ alkyl group, one or more substituted with _{G 4 C} 1 may be -C ₆ haloalkyl group, one or more may be substituted by _{G 4 C} 3 _{~C 6} cycloalkyl group, or one or more may be substituted by _{G 4 C} 1 -C ₆ alkoxy group.
However, two Y on the same carbon can also represent (= O) or (= S), and can also form (C = O) or (C = S). Two Ys may be bonded to each other to represent a carbocyclic or heterocyclic ring. Y may be the same or different.
G ₄ is a cyano group, a C ₁ -C ₆ alkoxy group, a C ₁ -C ₆ alkylthio group, a C ₁ -C ₆ alkylamino group, a di C ₂ -C ₆ alkylamino group, or a C ₁ -C ₆ alkoxy group. Represents a carbonyl group,
M represents an integer of 0 to 4,
N represents an integer of 0 to 8,
The p represents an integer of 0 to 2;
Q and r each represent an integer of 0 to 1;
The aryl group is a phenyl group or a naphthyl group,
The heterocyclic ring is pyridine, pyridazine, pyrazine, pyrimidine, triazine, tetrazine, furan, thiophene, pyrrole, pyrazole, imidazole, triazole, tetrazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, quinoline, isoquinoline , Cinnoline, phthalazine, quinoxaline, quinazoline, benzofuran, benzothiophene, indole, indazole, benzimidazole, benzotriazole, benzoxazole, benzisoxazole, benzothiazole, benzoisothiazole, benzoxiadiazole, pyrrolidine, tetrahydrofuran, Tetrahydrothiophene, piperidine, tetrahydropyran, or tetrahydride Thiopyran,
The substituted phenylpiperazine compound according to claim 1 or a salt thereof. Wherein A is one or more of which can be substituted by _{G 1 C} 1 -C ₅ alkyl _groups, C 2 -C ₅ alkenyl _groups, C 2 -C ₅ alkynyl _groups, C 3 -C ₅ cycloalkyl groups, C _{1 to} C ₈ haloalkyl group, or C _{2 to} C ₈ haloalkenyl group,
G ₁ represents a cyano group, a C _{3 to} C ₆ cycloalkyl group,
R is a hydrogen atom, a formyl group, a halocarbonyl group, a thioformyl group, a C ₁ -C ₁₈ alkyl group that may be substituted with one or more G ₂ , and a C that is optionally substituted with one or more G _{2. 2} -C ₈ alkenyl group, one or more optionally substituted with _{G 2 C 2} ~C ₈ alkynyl group, one or more optionally _C 3 substituted by _{G 3} of -C ₆ cycloalkyl group, one more _{G 2} which may be substituted, _C 1 -C ₈ alkylcarbonyl group, one or more _C 1 may be substituted by _{G 2} -C ₈ alkyl thio group, substituted with one or more _{G 2} which may _C 2 -C ₈ alkenylcarbonyl group, one or more optionally substituted with _{G 3 C 3 ~C 8} cycloalkyl group, one or more optionally substituted with _{G 3 C 3 ~C 8} A cycloalkylthiocarbonyl group, one or more _{G 2} which may be substituted, _C 1 -C ₈ alkoxycarbonyl group, one or more _C 1 may be substituted by _{G 2} -C ₈ alkylaminocarbonyl group, substituted with one or more _{G 2} which may _C 1 -C ₈ alkylamino thiocarbonyl group, one or more _{G 2} that is substituted di _C 2 may be -C ₈ alkylaminocarbonyl group, one or more which may be di-C substituted with _{G 2 2} -C ₈ alkylaminothiocarbonyl group, a hydroxyl group, a halosulfonyl group, one or more substituted with _{G 2 C} 1 may be -C ₈ alkylsulfonyl group may be substituted by one or more _{G 2} C ₂ -C ₈ alkenylsulfonyl group, one or more _{G 3-substituted C} 3 -C ₈ optionally cycloalkylsulfonyl group, one or more _C 1 may be substituted by _{G 2} -C ₈ alkylamino Ruhoniru group, one or more substituted with G ₂ good di C ₂ -C ₈ alkylaminosulfonyl group optionally, one or more which may be a benzyl group substituted with G _3, substituted by one or more G ₃ good benzoyl group optionally one or more G ₃ which may be substituted with a heterocyclic carbonyl group, one or more G ₃ which may be substituted with a phenyl thio group, substituted with one or more G ₃ also heterocyclic thiocarbonyl group, one or more G ₃ in which may be substituted benzoyloxy group, one or more G ₃ which may be substituted with a phenoxycarbonyl group, substituted with one or more G ₃ also heterocyclic oxycarbonyl group, one or more G ₃ which may be substituted with a phenylamino group, one or more may be substituted by G ₃ heterocyclic aminocarbonyl group, by one or more G ₃ Even if it is replaced Phenyl sulfonyl group, one or more may be substituted by G ₃ heterocyclic sulfonyl group, one or more G ₃ in an optionally substituted phenyl aminosulfonyl group, optionally substituted by one or more G ₃ A good phenyl group, or a heterocycle optionally substituted with one or more G ₃ ;
G ₂ is a halogen atom, a cyano group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkylthio group, a C ₁ -C ₄ alkylamino group, or a di C ₂ -C. ₆ alkylamino _group, C 1 -C ₄ alkylsulfinyl _group, C 1 -C ₄ alkylcarbonyl _group, C 3 -C ₆ cycloalkyl _group, C 1 -C ₆ alkoxycarbonyl _group, C 1 -C ₄ alkoxyimino group , C ₂ -C ₄ alkynyloxy imino group, one or more G ₅ with a phenyl group which may be substituted with one or more heterocyclic ring which may be substituted with G _5, substituted by one or more G ₅ An optionally substituted benzoyl group, or a phenoxy group optionally substituted by one or more G ₅ ;
G ₃ is a halogen atom, a cyano group, a nitro group, a C ₁ -C ₄ alkyl group, a C ₂ -C ₅ alkenyl group, a C ₂ -C ₅ alkynyl group, a C ₁ -C ₄ haloalkyl group, or a C ₃ -C. ₆ cycloalkyl group, C ₁ -C ₄ alkoxy group, C ₁ -C ₄ haloalkoxy group, C ₁ -C ₄ alkylthio group, C ₁ -C ₄ haloalkylthio group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ haloalkylsulfinyl _group, C 1 -C ₄ alkylsulfonyl _group, C 1 -C ₄ haloalkylsulfonyl _group, C 1 -C ₆ alkylamino group, _di-C 2 -C ₆ alkylamino _group, C 2 -C ₆ alkenyl amino _group, C 2 -C ₄ alkynyl amino _groups, C 1 -C ₆ alkylcarbonyl _group, C 1 -C ₆ alkoxycarbonyl _group, C 1 -C ₆ alkylamino Carbonyl group, C ₁ -C ₆ haloalkylcarbonyl aminocarbonyl group, one or more G ₅ which may be substituted with a phenyl group, one or more G ₅ which may be substituted with a phenoxy group, with one or more G ₅ optionally substituted benzoyl group, one or more G ₅ heterocyclic ring which may be substituted by or one or more substituted with G ₅ may be a heterocyclic oxy group,
G ₅ is a halogen atom, a cyano group, a nitro group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₄ alkoxy group, a C _1- A C ₄ haloalkoxy group, a C ₁ -C ₄ alkylthio group, or a C ₁ -C ₄ haloalkylthio group,
Wherein X represents a halogen atom, a cyano group or C ₁ -C ₄ alkyl group optionally substituted by a halogen atom,
Wherein Y represents a halogen atom, an oxygen _atom, a C 3 -C ₆ cycloalkyl group or a _C 1 -C ₄ alkyl group.
However, two Y on the same carbon can also represent (= O) and can also form (C = O).
M represents an integer of 1 to 3,
N represents an integer of 0 to 4,
The p represents an integer of 0 to 2;
Q and r each represent an integer of 0 to 1;
The heterocyclic ring is pyridine, pyrimidine, furan, thiophene, pyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, quinoline, isoquinoline, indole, benzoisothiazole, benzothiadiazole, tetrahydrofuran, tetrahydrothiophene, piperidine , Tetrahydropyran, or tetrahydrothiopyran,
The substituted phenyl piperazine compound according to claim 1 or 2, or a salt thereof. Wherein _A represents a C 2 -C ₄ haloalkyl group,
R is a hydrogen atom, a formyl group, a chlorocarbonyl group, a thioformyl group, a C ₁ -C ₁₅ alkyl group that may be substituted with one or more G ₂ , and a C that is optionally substituted with one or more G _{2. 2} -C ₅ alkenyl group, one or more optionally substituted with _{G 2 C 2 ~C 5} alkynyl group, one or more optionally substituted with _{G 2 C} 1 -C ₆ alkylcarbonyl group, one more optionally substituted with _{G 2 C} 1 -C ₆ alkylthiocarbonyl group, one or more optionally substituted with _{G 2 C 2 ~C 6} alkenyl group, substituted with one or more _{G 3} C ₃ -C ₈ cycloalkylcarbonyl group, C ₃ -C ₈ cycloalkylthiocarbonyl group optionally substituted by one or more G ₃ , C ₁ -C optionally substituted by one or more G _{2 6} alkoxycarbonyl group One or more substituted with _{G 2 C} 1 may be -C ₅ alkylaminocarbonyl group, one or more optionally substituted with _{G 2 C} 1 -C ₅ alkylamino thiocarbonyl group, one or more G di C ₂ may be substituted by ₂ -C ₅ alkylaminocarbonyl group, one or more may be substituted by G ₂ di C ₂ -C ₅ alkylaminothiocarbonyl group, a hydroxyl group, chlorosulfonyl group, 1 one or more substituted with _{G 2 C} 1 may be -C ₆ alkylsulfonyl group, one or more optionally substituted with _{G 2 C 2} ~C ₆ alkenyl sulfonyl group is substituted with one or more _{G 3} which may be _C 3 -C ₈ cycloalkylsulfonyl group, one or more optionally substituted with _{G 2 C} 1 -C ₈ alkylaminosulfonyl group, one or more _{G 2} good di _{C 2} may be substituted with ~C Alkylaminosulfonyl group, one or more optionally substituted benzyl group in G _3, one or more may benzoyl group optionally substituted by G _3, one or more heterocyclic carbonyl optionally substituted with G ₃ group, one or more G ₃ which may be substituted with a phenyl thio group, one or more G ₃ in which may be substituted benzoyloxy group, one or more G ₃ which may be substituted with a phenoxycarbonyl group one or more substituted with G ₃ may be phenylaminocarbonyl group, one or more G ₃ which may be phenylsulfonyl group substituted with one or more may be substituted by G ₃ heterocyclic sulfonyl group , one or more phenyl group which may be substituted with G ₃ or one or more substituted with G ₃ represents an optionally heterocycle,
G ₂ represents a halogen atom, a cyano group, a C _{3 to} C ₆ cycloalkyl group, a C _{1 to} C ₄ alkoxy group, a C _{1 to} C ₄ alkylthio group, a C _{1 to} C ₄ alkylsulfinyl group, or a C _{1 to} C _4. alkylcarbonyl _group, substituted with C 3 -C ₆ cycloalkyl _group, C 1 -C ₄ alkoxycarbonyl _group, C 1 -C ₄ alkoxyimino _group, C 2 -C ₄ alkynyloxy imino group, one or more _{G 5} phenyl group which may be one or more heterocyclic ring which may be substituted with G _5, which may be substituted one or more optionally substituted benzoyl group G ₅ or by one or more G _5, Represents a phenoxy group,
G ₃ is a halogen atom, a cyano group, a nitro group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group, a C _1- C ₄ alkylthio _groups, C 1 -C ₄ haloalkylthio _group, C 1 -C ₄ alkylsulfinyl _group, C 1 -C ₄ haloalkylsulfinyl _group, C 1 -C ₄ alkylsulfonyl _group, C 1 -C ₄ haloalkylsulfonyl group, C ₁ -C ₄ alkylamino group, _di-C 2 -C ₄ alkylamino _group, C 1 -C ₄ alkoxycarbonyl _group, C 1 -C ₄ alkylaminocarbonyl _group, C 1 -C ₄ halo alkylaminocarbonyl group, one more G ₅ which may be substituted with a phenyl group, one or more G ₅ which may be substituted with a phenoxy group, optionally substituted by one or more G ₅ A heterocyclic ring, or a heterocyclic oxy group optionally substituted with one or more G ₅ ,
G ₅ represents a halogen atom, a cyano group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, or a C ₁ -C ₄ alkoxy group,
Wherein X represents a halogen atom, a cyano group, or a _C 1 -C ₄ alkyl group,
Wherein Y represents an oxygen _atom, C 1 -C ₄ alkyl or _C 3 -C ₆ cycloalkyl group,.
However, two Y on the same carbon can also represent (= O) and can also form (C = O).
M represents an integer of 1 to 2,
N represents an integer of 0 to 3,
The p represents an integer of 0 to 2;
Q and r each represent an integer of 0 to 1;
The heterocyclic ring is pyridine, thiophene, triazole, oxazole, thiazole, quinoline, isoquinoline, indole, benzoisothiazole, benzothiadiazole, tetrahydrofuran, piperidine, tetrahydropyran, or tetrahydrothiopyran,
The substituted phenylpiperazine compound according to any one of claims 1 to 3, or a salt thereof.   The pest control agent containing at least 1 type of the substituted phenyl piperazine compound or its salt in any one of Claims 1-4.