WO2015025826A1

WO2015025826A1 - Substituted phenyl ether compound and pest control agent

Info

Publication number: WO2015025826A1
Application number: PCT/JP2014/071593
Authority: WO
Inventors: 鈴木　潤; 尾上　真治; 英宏田地野; 竜太大野; 仁若林; 優太小林; 政時野尻; 美和尾上; 大悟岡村; 勝哉山岸
Original assignee: 北興化学工業株式会社
Priority date: 2013-08-21
Filing date: 2014-08-18
Publication date: 2015-02-26
Also published as: TW201536725A

Abstract

The purpose of the present invention is to provide: a novel substituted phenyl ether compound which has a control effect against pests; and a pest control agent which contains this substituted phenyl ether compound as an active ingredient. A substituted phenyl ether compound represented by formula (1) is provided as a solution.

Description

Substituted phenyl ether compounds and pest control agents

The present invention relates to a novel substituted phenyl ether compound and a pest control agent comprising the same as an active ingredient.

To date, many pesticides have been used to control pests in agricultural and horticultural settings or animals such as pets and livestock. However, the pesticides are not effective enough or are initially effective. Even if it is made, pests become resistant to these drugs, and the control effect may be reduced. In addition, even if a pest control agent is sprayed and controlled, it will fly from the outside or the egg pest will hatch at the time of spraying, generating new pests. Residual properties that exert a control effect on the generated pests are required. Drugs that do not have after-effects are disadvantageous in that the number of sprays increases, which is troublesome and pests can easily acquire resistance. In addition, some of the widely used pest control agents are not only harmful to pests but also have strong toxicity to human livestock and fish and shellfish, and some are toxic to natural enemies. There are very few pest control agents that accumulate in the environment and cause environmental pollution, and exhibit high performance in all aspects. Therefore, even against pests that have acquired resistance to conventionally used pest control agents, they exhibit a sufficient control effect at a low dose, and the control effect continues even after spraying, and against useful organisms. Therefore, the development of a new pest control agent that is highly safe and has no adverse environmental impact is eagerly desired.

By the way, insecticidal and acaricidal activities relating to substituted phenyl ether compounds have been known so far. For example, Patent Document 1 describes a compound having a phenyl ether skeleton similar to the compound according to the present invention. In the general formula of Patent Document 1, R ² represents only a (C ₁ -C ₆ ) alkyl group, and the haloalkyl group and cycloalkylalkyl group of A in Formula (1) shown in the present invention are not described.
Patent Documents 2 and 3 describe diphenyl ether compounds useful as insecticides and acaricides. Patent Documents 2 and 3 are compounds in which two benzene rings form an ether bond directly with an oxygen atom, but the compounds in which two benzene rings form an ether bond with an oxygen atom containing an alkylene chain as in the present invention. There is no description.

Patent Document 4 describes amidine compounds containing 3-substituted phenyl sulfide useful as insecticides and acaricides. Although the compound described in Patent Document 4 has an amidine skeleton at the 3-position of the benzene ring of phenyl sulfide, there is no description of a substituted phenyl ether skeleton as in the present invention. Patent Documents 5 and 6 describe 3-heterocyclic substituted phenyl sulfide compounds useful as insecticides and acaricides. Although the compounds described in Patent Documents 5 and 6 each have a triazole ring and a pyrazole ring at the 3-position of the benzene ring of phenyl sulfide, there is no description of a substituted phenyl ether skeleton as in the present invention.

In addition, N-substituted aniline compounds exhibiting insecticidal activity similar to the present invention have been known so far. For example, although the compound described in Patent Document 7 has an aminocarbonyl group substituted at the 3-position of aniline, there is no description of an aniline compound substituted with phenoxyalkyl as in the present invention.

Patent Document 8 describes an alkylphenyl sulfide compound having a pest control effect. In the general formula [1] of Patent Document 8, R ⁴ represents an alkyl group substituted with a phenyl group (the group may be substituted with R ⁶ ), and therefore shows a compound similar to the compound of the present invention. However, no amino group is described in R ⁶ corresponding to the N-substituted aniline skeleton, which is a feature of the compound of the present invention.

Patent Document 9 describes a compound similar to the compound according to the present invention. In the general formula A and D ″ in Patent Document 9, there is no description of a haloalkylthio group, a cycloalkylalkylthio group, a haloalkylsulfinyl group, a cycloalkylalkylsulfinyl group, or the like, and no description of insecticidal activity.

Japanese Unexamined Patent Publication No. Sho 63-41451 Japanese Unexamined Patent Publication No. 51-79723 International Publication No. 2013/111864 Pamphlet International Publication No. 2007/131680 Pamphlet International Publication No. 2006/043635 Pamphlet International Publication No. 2009/051245 Pamphlet International Publication No. 2005/021488 Pamphlet International Publication No. 2013/157229 Pamphlet International Publication No. 1999/062871 Pamphlet

An object of the present invention is to provide a novel substituted phenyl ether compound having a safe and pest control effect and a pest control agent characterized by containing this as an active ingredient.

As a result of intensive studies to solve the above problems, the present inventor has found that the substituted phenyl ether compound represented by the following formula (1) has an excellent control effect against pests, and completes the present invention. It came to.

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

In the above formula (1), A is a C ₂ -C ₅ haloalkyl group, a C ₂ -C ₅ haloalkenyl group, or an optionally substituted C ₃ -C ₈ cycloalkyl C ₁ -C ₄ alkyl group (the group is And may be mono-substituted or poly-substituted by a halogen atom or a C ₁ -C ₃ alkyl group.), N represents an integer of 0 to 2.
X ¹ and X ² are each independently a hydrogen atom, a halogen atom, a cyano group, a C ₁ -C ₆ alkyl group that may be substituted with a halogen atom, or a C ₁ -C ₆ alkoxy that may be substituted with a halogen atom. Group, a C ₃ -C ₆ cycloalkyl group, or an aryl group which may be substituted with a halogen atom. However, X ¹ and X ² cannot simultaneously be hydrogen atoms.
Y is a hydrogen atom, a halogen atom, a nitro group, a cyano group, an amino group, a formyl group, an optionally C _{1 ~} C ₆ alkyl group optionally substituted by a halogen atom, which may C ₁ be _~ C ₆ alkoxy substituted with a halogen atom group, optionally substituted C _{1 ~} C ₆ alkylthio group with a halogen atom, a halogen atom with optionally substituted C _{1 ~} C ₆ alkylsulfinyl group, optionally substituted C _{1 ~} C ₆ alkylsulfonyl halogen atom Group, C ₁ -C ₆ alkylamino group, di-C ₁ -C ₆ alkylamino group, C ₁ -C ₆ alkylcarbonyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkoxyiminomethyl group, halogen aryl group which may be substituted with atoms, an optionally substituted aryloxy group (in which a halogen atom, a cyano group, C 1 _~ C ₃ alkyl group C ₁ ~ _{C 3} haloalkyl _group, _C 1 ~ C ₃ alkoxy _group, _C 1 ~ C ₃ haloalkoxy _group, _C 1 ~ C ₃ alkylthio _group, _C 1 ~ C ₃ haloalkylthio _group, _C 1 ~ C ₃ alkylsulfinyl group Monosubstituted by a C ₁ -C ₃ haloalkylsulfinyl group, a C ₁ -C ₃ alkylsulfonyl group, a C ₁ -C ₃ haloalkylsulfonyl group, a C ₁ -C ₃ alkylcarbonyl group, or a C ₁ -C ₃ alkoxycarbonyl group An optionally substituted arylthio group (this group is a halogen atom, a cyano group, a C ₁ -C ₃ alkyl group, a C ₁ -C ₃ haloalkyl group, a C ₁ -C ₃ alkoxy group, C ₁ ~ _{C 3} haloalkoxy _group, _C 1 ~ C ₃ alkylthio _group, _C 1 ~ C ₃ haloalkylthio _group, _C 1 ~ C ₃ Arukirusu Finiru _group, C 1 ~ _{C 3} haloalkylsulfinyl _group, a mono by C 1 ~ _{C 3} alkylsulfonyl _group, C 1 ~ _{C 3} haloalkylsulfonyl _group, C 1 ~ _{C 3} alkyl group or a _C 1 ~ _{C 3} alkoxycarbonyl group, Substituted or polysubstituted.), Optionally substituted arylsulfinyl group (the group is a halogen atom, cyano group, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group, C ₁ -C ₃₎ An alkoxy group, a C ₁ -C ₃ haloalkoxy group, a C ₁ -C ₃ alkylthio group, a C ₁ -C ₃ haloalkylthio group, a C ₁ -C ₃ alkylsulfinyl group, a C ₁ -C ₃ haloalkylsulfinyl group, a C _1- C ₃ alkylsulfonyl group, C ₁ -C ₃ haloalkylsulfonyl group, C ₁ -C ₃ alkylcarbonyl group, Alternatively, it may be monosubstituted or polysubstituted by a C ₁ -C ₃ alkoxycarbonyl group. ), An optionally substituted arylsulfonyl group (the group is a halogen atom, a cyano group, a C ₁ -C ₃ alkyl group, a C ₁ -C ₃ haloalkyl group, a C ₁ -C ₃ alkoxy group, a C ₁ -C ₃ halo group) Alkoxy group, C ₁ -C ₃ alkylthio group, C ₁ -C ₃ haloalkylthio group, C ₁ -C ₃ alkylsulfinyl group, C ₁ -C ₃ haloalkylsulfinyl group, C ₁ -C ₃ alkylsulfonyl group, C _1- A C ₃ haloalkylsulfonyl group, a C ₁ -C ₃ alkylcarbonyl group, or a C ₁ -C ₃ alkoxycarbonyl group may be mono- or polysubstituted), or a C ₇ -C optionally substituted with a halogen atom _{11 represents an} aralkyloxy group, and m represents an integer of 1 to 5. When m represents an integer of 2 to 5, Y may be the same or different. Further, when m represents an integer of 2 or more, _and bind adjacent each other in the _{_{Y, -OCH 2 O -, - OCF}} 2 O -, - OCH 2 CH 2 O -, - OCF 2 CH 2 O-, Alternatively, —OCF ₂ CF ₂ O— may be represented.
R ¹ and R ² are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a C ₁ -C ₆ alkyl group that may be substituted with a halogen atom, or a C ₁ -C that may be substituted with a halogen atom. _{4 represents an} alkoxy group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₄ alkylcarbonyloxy group, or a benzoyloxy group, and p represents an integer of 1 to 5. When p represents an integer of 2 to 5, R ¹ and R ² on different carbon atoms may be the same or different. Further, R ¹ and R ² on the same carbon atom can be each represented by (═O) or (═S) by being bonded to one oxygen atom or sulfur atom. Also, R ¹ and R ² on the same carbon atom can be bonded simultaneously to represent a C ₁ -C ₄ alkoxyimino group. R ¹ and R ² on the same carbon atom can be bonded to each other to form a 3-membered ring, 4-membered ring, 5-membered ring or 6-membered ring with 2 to 5 alkylene groups.
Z represents an oxygen atom, a sulfur atom, a sulfinyl group, or a sulfonyl group, and q represents an integer of 0 or 1. However, p and q cannot be 1 at the same time.

The second aspect of the present invention relates to a pest control agent containing a substituted phenyl ether compound represented by the above formula (1).

The third aspect of the invention according to the present application relates to a production intermediate represented by the following formula (2).

In the above formula (2), A is an optionally substituted C ₃ -C ₈ cycloalkylmethyl group (the group may be mono-substituted or poly-substituted by a fluorine atom or a C ₁ -C ₃ alkyl group). N represents an integer of either 0 or 1.
X ¹ represents a C ₁ -C ₄ alkyl group, and X ² represents a hydrogen atom, a halogen atom, or a C ₁ -C ₄ alkyl group.

The fourth aspect of the invention according to the present application relates to an N-substituted aniline compound represented by the following formula (1-6).

In the above formula (1-6), A ¹⁰⁰ represents a C ₂ -C ₅ haloalkyl group or a C ₃ -C ₆ cycloalkyl C ₁ -C ₃ alkyl group, and n represents an integer of 0 to 2 .
X ¹⁰¹ and X ¹⁰² are each independently a hydrogen atom, a halogen atom, a cyano group, a C ₁ -C ₆ alkyl group that may be substituted with a halogen atom, or a C ₁ -C ₆ that may be substituted with a halogen atom. An alkoxy group is shown. However, X ¹⁰¹ and X ¹⁰² cannot simultaneously be hydrogen atoms.
Y ¹⁰⁰ represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a formyl group, a C ₁ -C ₆ alkyl group that may be substituted with a halogen atom, a C ₁ -C ₆ alkoxy group that may be substituted with a halogen atom, optionally substituted C _{1 ~} C ₆ alkylthio group with a halogen atom, a halogen atom with optionally substituted C _{1 ~} C ₆ alkylsulfinyl group, optionally substituted C _{1 ~} C ₆ alkylsulfonyl group with a halogen atom, A C ₁ -C ₆ alkylcarbonyl group, a C ₁ -C ₆ alkoxycarbonyl group, or a C ₁ -C ₆ alkoxyiminomethyl group, and v represents an integer of 1 to 4. When v represents an integer of 2 to 4, Y ¹⁰⁰ may be the same or different.
R ^101a and ^{R 102a} are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, an optionally _C 1 ~ _{C 6} alkyl group optionally substituted by a halogen atom or _C 1 ~ optionally substituted by a halogen atom, It shows the C ₄ alkoxy groups. Further, R ^101a and R ^102a on the same carbon atom can be each represented by (═O) or (═S) by being bonded to one oxygen atom or sulfur atom. Also, R ^101a and R ^102a on the same carbon atom can be bonded simultaneously to represent a C ¹ -C ⁴ alkoxyimino group. R ^101a and R ^102a on the same carbon atom can be bonded to each other to form a 3-membered ring, 4-membered ring, 5-membered ring or 6-membered ring with 2 to 5 alkylene groups.
R ^101b and R ^102b each independently represent a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group that may be substituted with a halogen atom, or a C ₁ -C ₄ alkoxy group that may be substituted with a halogen atom. U represents an integer of either 0 or 1.

The fifth aspect of the present invention relates to a pest control agent comprising an N-substituted aniline compound represented by the above formula (1-6).

The sixth aspect of the present invention relates to a compound represented by the following formula (3), which is a production intermediate of the N-substituted aniline compound represented by the above formula (1-6).

In the above formula (3), G represents CO ₂ R ¹⁰³ (R ¹⁰³ represents a C ₁ -C ₄ alkyl group), or CH ₂ OR ¹⁰⁴ (R ¹⁰⁴ represents a hydrogen atom or a C atom optionally substituted with a halogen atom). ₁ -C ₄ alkylsulfonyl group, or arylsulfonyl group optionally substituted with C ₁ -C ₄ alkyl group.
Y ¹⁰¹ and Y ¹⁰² each independently represent a hydrogen atom (except when G represents CO ₂ R ³ ), a halogen atom, or a C ₁ -C ₄ alkyl group that may be substituted with a halogen atom. .
W ³ and W ⁴ each independently represent a hydrogen atom, a C ₁ -C ₆ alkylcarbonyl group that may be substituted with a halogen atom, a C ₁ -C ₆ alkoxycarbonyl group, or a C that may be substituted with a halogen atom. ₁ to C ₆ alkylsulfonyl group.

According to the present invention, it is possible to provide a novel substituted phenyl ether compound having a pest control effect and a pest control agent containing the substituted phenyl ether compound.

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

In the above formula (1), examples of the halogen atom or the halogen atom as a substituent include each element of fluorine, chlorine, bromine or iodine. The number of halogen atoms as substituents may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.

In the above formula (1), the C ₂ -C ₅ haloalkyl group represented by A includes a 2-fluoroethyl group, a 1-chloroethyl group, a 2-chloroethyl group, a 1-bromoethyl group, a 2-bromoethyl group, 2, 2-difluoroethyl group, 1,2-dichloroethyl group, 2,2-dichloroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, 1,1,2,2 -Tetrafluoroethyl group, pentafluoroethyl group, 2-bromo-2-chloroethyl group, 2-chloro-1,1,2,2-tetrafluoroethyl group, 1-chloro-1,2,2,2-tetra Fluoroethyl group, 1-chloropropyl group, 2-chloropropyl group, 3-chloropropyl group, 2-bromopropyl group, 3-bromopropyl group, 2-bromo-1-methylethyl group, 3-iodopropyl Pill group, 2,2,2-trifluoro-1-methylethyl group, 2,3-dichloropropyl group, 2,3-dibromopropyl group, 3,3,3-trifluoropropyl group, 3,3,3 -Trichloropropyl group, 3-bromo-3,3-difluoropropyl group, 3,3-dichloro-3-fluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 1-bromo-3,3 3-trifluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, heptafluoropropyl group, 2,3-dichloro-1,1,2,3,3-pentafluoropropyl group, 2- Chlorobutyl, 3-chlorobutyl, 4-chlorobutyl, 2-chloro-1,1-dimethylethyl, 4-bromobutyl, 3-bromo-2-methylpropyl, 2-bromo-1,1-di Tylethyl group, 2,2-dichloro-1,1-dimethylethyl group, 2-chloro-1-chloromethyl-2-methylethyl group, 4,4,4-trifluorobutyl group, 3,3,3-trimethyl Fluoro-1-methylpropyl group, 3,3,3-trifluoro-2-methylpropyl group, 2,3,4-trichlorobutyl group, 2,2,2-trichloro-1,1-dimethylethyl group, 4 -Chloro-4,4-difluorobutyl group, 4,4-dichloro-4-fluorobutyl group, 4-bromo-4,4-difluorobutyl group, 2,4-dibromo-4,4-difluorobutyl group, 3 , 4-dichloro-3,4,4-trifluorobutyl group, 3,3-dichloro-4,4,4-trifluorobutyl group, 4-bromo-3,3,4,4-tetrafluorobutyl group, 4-Bromo-3-chloro- 3,4,4-trifluorobutyl group, 2,2,3,3,4,4-hexafluorobutyl group, 2,2,3,4,4,4-hexafluorobutyl group, 2,2,3 , 3,4,4,4-heptafluorobutyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, nonafluorobutyl group, 4-chloro-1,1,2, Examples include 2,3,3,4,4-octafluorobutyl group, and more preferably 2,2,2-trifluoroethyl group.

In the above formula (1), the C ₂ -C ₅ haloalkenyl group represented by A includes bromovinyl group, chlorovinyl group, 3,3-dichloro-2-propenyl group, 3,3,3-trifluoro- 1-propenyl group 4,4-difluoro-3-butenyl group, 3,4,4-trifluoro-3-butenyl group, and the like, more preferably 3,3,3-trifluoro-1-propenyl group Is mentioned.

In the formula (1), as _C 3 ~ _{C 8} cycloalkyl _C 1 ~ _{C 4} alkyl group moiety of the optionally substituted _C 3 be ~ _{C 8} cycloalkyl _C 1 ~ _{C 4} alkyl group represented by A, Cyclopropylmethyl group, 1-cyclopropylethyl group, 2-cyclopropylethyl group, 1-cyclopropylpropyl group, 2-cyclopropylpropyl group, 3-cyclopropylpropyl group, 1-cyclopropylbutyl group, 2-cyclo Propylbutyl group, 3-cyclopropylbutyl group, 4-cyclopropylbutyl group, cyclobutylmethyl group, 1-cyclobutylethyl group, 2-cyclobutylethyl group, cyclopentylmethyl group, cyclohexylmethyl group, cycloheptylmethyl group, A cyclooctylmethyl group is mentioned, More preferably, a cyclopropylmethyl group is mentioned. The halogen atom as a substituent has the same definition as described above, and examples of the C ₁ -C ₃ alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, and more preferably a fluorine atom or A methyl group is mentioned.

In the above formula (1), n represents any integer of 0-2. When n is 0, the oxygen atom (O) is not added to the sulfur atom (S), and when n is 1, one oxygen atom (O) is added to the sulfur atom (S) to form a sulfinyl group. (S = O) is formed. When n is 2, two oxygen atoms (O) are added to the sulfur atom (S) to form a sulfonyl group (O = S = O).

In the above formula (1), the halogen atom have the same definition as above, _C 1 ~ _{C 6} alkyl group portion of the good _C 1 ~ _{C 6} alkyl group optionally substituted by a halogen atom represented by ^{X 1} and ^{X 2} As methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, 2-pentyl Group, 3-pentyl group, tert-pentyl group, n-hexyl group, i-hexyl group, 2-hexyl group, 3-hexyl group and the like, more preferably methyl group.

The formula (1), as the _C 1 ~ _{C 6} alkoxy group portion of which may _C 1 be ~ _{C 6} alkoxy group substituted with a halogen atom represented by ^{X 1} and ^{X 2,} a methoxy group, an ethoxy radical, n -Propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, sec-butoxy group, tert-butoxy group and the like, more preferably methoxy group.

In the above formula (1), examples of the C ₃ -C ₆ cycloalkyl group represented by X ¹ and X ² include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like, and more preferably cyclopropyl group Groups.

In the above formula (1), examples of the aryl group portion of the aryl group which may be substituted with a halogen atom represented by X ¹ or X ² include a phenyl group and a naphthyl group, and more preferably a phenyl group. Can be mentioned.

In the above formula (1), the halogen atom represented by Y has the same definition as above, preferably a fluorine atom, a chlorine atom, or a bromine atom, more preferably a fluorine atom or a chlorine atom, and most preferably a fluorine atom. Is preferred. The _C 1 ~ _{C 6} alkyl group portion of the optionally substituted _C 1 ~ _{C 6} alkyl group by a halogen atom, a methyl group, an ethyl group, n- propyl group, i- propyl, n- butyl, i- Butyl, sec-butyl, tert-butyl, pentyl, neopentyl, 2-pentyl, 3-pentyl, tert-pentyl, hexyl, i-hexyl, 2-hexyl, 3-hexyl Group etc. are mentioned, A methyl group is mentioned more suitably.

In the above formula (1), as the _C 1 ~ _{C 6} alkoxy group moiety of the optionally _C 1 ~ _{C 6} alkoxy group optionally substituted by a halogen atom represented by Y, a methoxy group, an ethoxy group, n- propoxy group, An i-propoxy group, an n-butoxy group, an i-butoxy group, a sec-butoxy group, a tert-butoxy group, and the like are preferable, and a methoxy group or an ethoxy group is more preferable.

In the above formula (1), as the _C 1 ~ _{C 6} alkylthio moiety good _C 1 ~ _{C 6} alkylthio group optionally substituted by a halogen atom represented by Y, methylthio group, ethylthio group, n- propylthio group, Examples include i-propylthio group, n-butylthio group, i-butylthio group, sec-butylthio group, and tert-butylthio group, and more preferable examples include methylthio group and ethylthio group.

The formula (1), as the C _{1 ~} C ₆ alkylsulfinyl group moiety of the optionally substituted C _{1 ~} C ₆ alkylsulfinyl group by a halogen atom represented by Y, methylsulfinyl group, ethylsulfinyl radical, n -Propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group, i-butylsulfinyl group, sec-butylsulfinyl group, tert-butylsulfinyl group, more preferably methylsulfinyl group or ethylsulfinyl group Can be mentioned.

The formula (1), as the C _{1 ~} C ₆ alkylsulfonyl group moiety of optionally substituted C _{1 ~} C ₆ alkylsulfonyl group by a halogen atom represented by Y, methylsulfonyl group, ethylsulfonyl radical, n -Propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group, more preferably methylsulfonyl group or ethylsulfonyl group Can be mentioned.

In the above formula (1), the C ₁ -C ₆ alkylamino group represented by Y is a methylamino group, ethylamino group, n-propylamino group, i-propylamino group, n-butylamino group, i -Butylamino group, sec-butylamino group, tert-butylamino group are preferable, and methylamino group or ethylamino group is more preferable.

In the above formula (1), the di-C ₁ -C ₆ alkylamino group represented by Y includes a dimethylamino group, a methylethylamino group, a diethylamino group, a di-n-propylamino group, a methyl n-propylamino group, Examples include ethyl n-propylamino group, di-i-propylamino group, di-n-butylamino group, di-i-butylamino group, disec-butylamino group, and ditert-butylamino group, and more preferred is dimethyl An amino group or a diethylamino group is mentioned.

In the above formula (1), examples of the C ₁ -C ₆ alkylcarbonyl group represented by Y include an acetyl group, a propionyl group, a butyryl group, an i-butyryl group, a valeryl group, a pivaloyl group, and the like. Includes an acetyl group. The number of carbon atoms of the alkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1), the C ₁ -C ₆ alkoxycarbonyl group represented by Y is a methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, tert -Butoxycarbonyl group, etc. are mentioned, More preferably, a methoxycarbonyl group or an ethoxycarbonyl group is mentioned. 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), the C ₁ -C ₆ alkoxyiminomethyl group represented by Y includes a methoxyimino group, an ethoxyimino group, an n-propoxyimino group, an i-propoxyimino group, an n-butoxyimino group, Examples thereof include a tert-butoxyimino group, and more preferably a methoxyimino group.

In the above formula (1), examples of the aryl group portion of the aryl group which may be substituted with a halogen atom represented by Y include a phenyl group and a naphthyl group, and more preferably a phenyl group.

In the above formula (1), examples of the aryloxy group moiety of the optionally substituted aryloxy group represented by Y include a phenoxy group and a naphthyloxy group, and more preferably a phenoxy group. Halogen atom as a substituent have the same definition as above, methyl group is a C 1 _~ C ₃ alkyl group, an ethyl group, n- propyl group, i- propyl group and the like, C 1 _~ C ₃ haloalkyl group Examples thereof include a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group and the like, and examples of the C ₁ -C ₃ alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, and an i-propoxy group. Examples of the C ₁ -C ₃ haloalkoxy group include a difluoromethoxy group, a trifluoromethoxy group, and a 2,2,2-trifluoroethoxy group, and examples of the C ₁ -C ₃ alkylthio group include a methylthio group. , ethylthio group, n- propylthio group, i- propylthio group and the _like, difluoromethyl as C 1 ~ _{C 3} haloalkylthio group O group, trifluoromethylthio group, 2,2,2-trifluoroethyl thio group and the like, and the C 1 _~ C ₃ alkylsulfinyl group methylsulfinyl group, ethylsulfinyl group, n- propyl sulfinyl group, i- Propylsulfinyl group and the like, and C ₁ -C ₃ haloalkylsulfinyl groups include difluoromethylsulfinyl group, trifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group and the like, and C ₁ -C ₃ Examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, an i-propylsulfonyl group, and the like, and examples of the C ₁ -C ₃ haloalkylsulfonyl group include a difluoromethylsulfonyl group, a trifluoromethylsulfonyl group, 2,2, - it includes such trifluoroethyl sulfonyl group, C 1 _~ C ₃ alkylcarbonyl acetyl group as group, a propionyl group and the like, C 1 _~ C ₃ alkoxy Examples of the carbonyl group-methoxycarbonyl group, and ethoxycarbonyl group More preferably, a fluorine atom or a trifluoromethyl group is mentioned.

In the above formula (1), examples of the arylthio group part of the optionally substituted arylthio group represented by Y include a phenylthio group, a naphthylthio group, and the like, more preferably a phenylthio group. Substituent halogen atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group, C ₁ -C ₃ alkoxy group, C ₁ -C ₃ haloalkoxy group, C ₁ -C ₃ alkylthio group, C ₁ -C ₃ haloalkylthio group, C ₁ -C ₃ alkylsulfinyl group, C ₁ -C ₃ haloalkylsulfinyl group, C ₁ -C ₃ alkylsulfonyl group, C ₁ -C ₃ haloalkylsulfonyl group, C ₁ -C ₃ alkylcarbonyl The group C ₁ -C ₃ alkoxycarbonyl group has the same definition as above, and more preferably a fluorine atom or a trifluoromethyl group.

In the above formula (1), examples of the arylsulfinyl group portion of the optionally substituted arylsulfinyl group represented by Y include a phenylsulfinyl group, a naphthylsulfinyl group, and the like, more preferably a phenylsulfinyl group. . Substituent halogen atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group, C ₁ -C ₃ alkoxy group, C ₁ -C ₃ haloalkoxy group, C ₁ -C ₃ alkylthio group, C ₁ -C ₃ haloalkylthio group, C ₁ -C ₃ alkylsulfinyl group, C ₁ -C ₃ haloalkylsulfinyl group, C ₁ -C ₃ alkylsulfonyl group, C ₁ -C ₃ haloalkylsulfonyl group, C ₁ -C ₃ alkylcarbonyl The group C ₁ -C ₃ alkoxycarbonyl group has the same definition as above, and more preferably a fluorine atom or a trifluoromethyl group.

In the above formula (1), examples of the arylsulfonyl group moiety of the optionally substituted arylsulfonyl group represented by Y include a phenylsulfonyl group and a naphthylsulfonyl group, and more preferably a phenylsulfonyl group. . Substituent halogen atom, C ₁ -C ₃ alkyl group, C ₁ -C ₃ haloalkyl group, C ₁ -C ₃ alkoxy group, C ₁ -C ₃ haloalkoxy group, C ₁ -C ₃ alkylthio group, C ₁ -C ₃ haloalkylthio group, C ₁ -C ₃ alkylsulfinyl group, C ₁ -C ₃ haloalkylsulfinyl group, C ₁ -C ₃ alkylsulfonyl group, C ₁ -C ₃ haloalkylsulfonyl group, C ₁ -C ₃ alkylcarbonyl The group C ₁ -C ₃ alkoxycarbonyl group has the same definition as above, and more preferably a fluorine atom or a trifluoromethyl group.

In the above formula (1), as the C _{7 ~} C ₁₁ aralkyloxy group moiety of the optionally substituted C ₇ be _~ C ₁₁ aralkyloxy group with a halogen atom represented by Y, benzyloxy group, phenethyloxy group and the like More preferably, a benzyloxy group is mentioned.

In the above formula (1), m represents an integer of 1 to 5. When m is 1, Y is added to any one of the five carbon atoms (C) constituting the phenyl group. In addition, when m is 2 to 4, Y is added to any two or three or four of the carbon atoms (C), and when m is 5, all of the carbon atoms (C) are added. Y is added.

Among the combinations of Y and m, those in which Y is a fluorine atom, m is 3, and a fluorine atom is added to the 3, 4, and 5 positions of the phenyl group are preferable.

In the above formula (1), the halogen atom have the same definition as above, _C 1 ~ _{C 6} alkyl group portion of the good _C 1 ~ _{C 6} alkyl group optionally substituted by a halogen atom represented by ^{R 1} and ^{R 2} As methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, 2-pentyl Group, 3-pentyl group, tert-pentyl group, n-hexyl group, i-hexyl group, 2-hexyl group, 3-hexyl group and the like, more preferably methyl group or ethyl group.

In the formula (1), as the _C 1 ~ _{C 4} alkoxy group portion of the good _C 1 ~ _{C 4} alkoxy group optionally substituted by a halogen atom represented by ^{R 1} and ^{R 2,} a methoxy group, an ethoxy radical, n -Propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, sec-butoxy group, tert-butoxy group and the like, more preferably methoxy group.

In the above formula (1), examples of the C ₃ -C ₆ cycloalkyl group represented by R ¹ and R ² include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like, and more preferably cyclopropyl group Groups.

In the above formula (1), examples of the C ₁ -C ₄ alkylcarbonyloxy group represented by R ¹ and R ² include acetyloxy group, propionyloxy group, butyryloxy group, i-butyryloxy group, pivaloyloxy group and the like. More preferred is an acetyloxy group. The number of carbon atoms of the alkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In said formula (1), p shows the integer in any one of 1-5. When p is 1 to 5, each represents a methylene chain, an ethylene chain, a propylene chain, a butylene chain, or a pentylene chain. When p represents an integer of 2 to 5, R ¹ and R ² on different carbon atoms may be the same or different. Further, R ¹ and R ² on the same carbon atom can be each represented by (═O) or (═S) by being bonded to one oxygen atom or sulfur atom. Further, R ¹ and R ² on the same carbon atom can be bonded simultaneously to represent a C ₁ -C ₄ alkoxyimino group, such as a methoxyimino group. R ¹ and R ² on the same carbon atom can be bonded to each other to form a 3-membered ring, 4-membered ring, 5-membered ring or 6-membered ring with 2 to 5 alkylene groups.

In the above formula (1), Z represents an oxygen atom, a sulfur atom, a sulfinyl group or a sulfonyl group, more preferably an oxygen atom.

In the above formula (1), q represents an integer of 0 or 1. However, p and q cannot be 1 at the same time. When q is 0, Z is not included in the formula (1), and when q is 1, any atom of Z is added.

The N-substituted aniline compound according to the present invention has a substituted phenoxyalkyl-substituted aniline skeleton represented by the following formula (1-6) as a basic skeleton.

In the formula (1-6), examples of the halogen atom or the halogen atom as a substituent include each element of fluorine, chlorine, bromine or iodine. The number of halogen atoms as substituents may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.

In the above formula (1-6), the C ₂ -C ₅ haloalkyl group represented by A ¹⁰⁰ is a 2-fluoroethyl group, 1-chloroethyl group, 2-chloroethyl group, 1-bromoethyl group, 2-bromoethyl group 2,2-difluoroethyl group, 1,2-dichloroethyl group, 2,2-dichloroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, 1,1, 2,2-tetrafluoroethyl group, pentafluoroethyl group, 2-bromo-2-chloroethyl group, 2-chloro-1,1,2,2-tetrafluoroethyl group, 1-chloro-1,2,2, 2-tetrafluoroethyl group, 1-chloropropyl group, 2-chloropropyl group, 3-chloropropyl group, 2-bromopropyl group, 3-bromopropyl group, 2-bromo-1-methylethyl group, 3 -Iodopropyl group, 2,2,2-trifluoro-1-methylethyl group, 2,3-dichloropropyl group, 2,3-dibromopropyl group, 3,3,3-trifluoropropyl group, 3,3 , 3-trichloropropyl group, 3-bromo-3,3-difluoropropyl group, 3,3-dichloro-3-fluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 1-bromo-3, 3,3-trifluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, heptafluoropropyl group, 2,3-dichloro-1,1,2,3,3-pentafluoropropyl group, 2-chlorobutyl group, 3-chlorobutyl group, 4-chlorobutyl group, 2-chloro-1,1-dimethylethyl group, 4-bromobutyl group, 3-bromo-2-methylpropyl group, 2-bromo- , 1-dimethylethyl group, 2,2-dichloro-1,1-dimethylethyl group, 2-chloro-1-chloromethyl-2-methylethyl group, 4,4,4-trifluorobutyl group, 3,3 , 3-trifluoro-1-methylpropyl group, 3,3,3-trifluoro-2-methylpropyl group, 2,3,4-trichlorobutyl group, 2,2,2-trichloro-1,1-dimethyl Ethyl group, 4-chloro-4,4-difluorobutyl group, 4,4-dichloro-4-fluorobutyl group, 4-bromo-4,4-difluorobutyl group, 2,4-dibromo-4,4-difluoro Butyl group, 3,4-dichloro-3,4,4-trifluorobutyl group, 3,3-dichloro-4,4,4-trifluorobutyl group, 4-bromo-3,3,4,4-tetra Fluorobutyl group, 4-bromo- -Chloro-3,4,4-trifluorobutyl group, 2,2,3,3,4,4-hexafluorobutyl group, 2,2,3,4,4,4-hexafluorobutyl group, 2, 2,3,3,4,4,4-heptafluorobutyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, nonafluorobutyl group, 4-chloro-1,1 2,2,3,3,4,4-octafluorobutyl group and the like, more preferably 2,2,2-trifluoroethyl group.

In the above formula (1-6), the C ₃ -C ₆ cycloalkyl C ₁ -C ₃ alkyl group represented by A ¹⁰⁰ includes a cyclopropylmethyl group, a 1-cyclopropylethyl group, a 2-cyclopropylethyl group 1-cyclopropylpropyl group, 2-cyclopropylpropyl group, 3-cyclopropylpropyl group, 1-cyclopropylbutyl group, 2-cyclopropylbutyl group, 3-cyclopropylbutyl group, 4-cyclopropylbutyl group, Examples thereof include a cyclobutylmethyl group, a 1-cyclobutylethyl group, a 2-cyclobutylethyl group, a cyclopentylmethyl group, and a cyclohexylmethyl group, and more preferably a cyclopropylmethyl group.

In the above formula (1-6), n represents an integer of 0 to 2. When n is 0, the oxygen atom (O) is not added to the sulfur atom (S), and when n is 1, one oxygen atom (O) is added to the sulfur atom (S) to form a sulfinyl group. (S = O) is formed. When n is 2, two oxygen atoms (O) are added to the sulfur atom (S) to form a sulfonyl group (O = S = O).

In the above formula ^(1-6), the halogen atom represented by ^{X 101} and ^{X 102} represents the same definition as above, _C 1 ~ _{C 6} alkyl substituted _C 1 may be ~ _{C 6} alkyl group by a halogen atom The group part includes 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, neopentyl group, 2 -Pentyl group, 3-pentyl group, tert-pentyl group, n-hexyl group, i-hexyl group, 2-hexyl group, 3-hexyl group and the like are preferable, and methyl group is more preferable.

In the above formula ^(1-6), as the _C 1 ~ _{C 6} alkoxy group moiety of the optionally _C 1 ~ _{C 6} alkoxy group optionally substituted by a halogen atom represented by ^{X 101} and ^{X 102,} a methoxy group, an ethoxy group N-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, sec-butoxy group, tert-butoxy group and the like, more preferably methoxy group.

In the above formula ^(1-6), the halogen atom represented by ^{Y 100} represents the same definition as above, as a _C 1 ~ _{C 6} alkyl group portion of the optionally substituted _C 1 ~ _{C 6} alkyl group by a halogen atom Is methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, 2-pentyl , 3-pentyl group, tert-pentyl group, n-hexyl group, i-hexyl group, 2-hexyl group, 3-hexyl group and the like, more preferably methyl group.

The formula ^(1-6), as the _C 1 ~ _{C 6} alkoxy group moiety of the optionally _C 1 ~ _{C 6} alkoxy group optionally substituted by a halogen atom represented by ^{Y 100,} a methoxy group, an ethoxy group, n- A propoxy group, an i-propoxy group, an n-butoxy group, an i-butoxy group, a sec-butoxy group, a tert-butoxy group and the like are preferable, and a methoxy group and an ethoxy group are more preferable.

In the above formula ^(1-6), as the _C 1 ~ _{C 6} alkylthio moiety good _C 1 ~ _{C 6} alkylthio group optionally substituted by a halogen atom represented by ^{Y 100,} methylthio group, ethylthio group, n- Examples thereof include a propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, a sec-butylthio group, and a tert-butylthio group, and more preferably a methylthio group or an ethylthio group.

In the above formula (1-6), as C _{1 ~} C ₆ alkylsulfinyl group moiety of the optionally substituted C _{1 ~} C ₆ alkylsulfinyl group by a halogen atom represented by Y ¹⁰⁰ are methylsulfinyl group, ethylsulfinyl Group, n-propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group, i-butylsulfinyl group, sec-butylsulfinyl group, tert-butylsulfinyl group, more preferably methylsulfinyl group or ethyl A sulfinyl group is mentioned.

In the above formula (1-6), the C ₁ -C ₆ alkylsulfonyl group moiety of the C ₁ -C ₆ alkylsulfonyl group which may be substituted with a halogen atom represented by Y ¹⁰⁰ includes a methylsulfonyl group, ethylsulfonyl Group, n-propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group, more preferably methylsulfonyl group or ethyl A sulfonyl group is mentioned.

In the above formula (1-6), examples of the C ₁ -C ₆ alkylcarbonyl group represented by Y ¹⁰⁰ include an acetyl group, a propionyl group, a butyryl group, an i-butyryl group, a valeryl group, and a pivaloyl group. More preferred is an acetyl group. The number of carbon atoms of the alkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1-6), the C ₁ -C ₆ alkoxycarbonyl group represented by Y ¹⁰⁰ includes a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and an n-butoxycarbonyl group. Group, tert-butoxycarbonyl group and the like, more preferably methoxycarbonyl group and ethoxycarbonyl group. 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 (1-6), the C ₁ -C ₆ alkoxyiminomethyl group represented by Y ¹⁰⁰ includes a methoxyiminomethyl group, an ethoxyiminomethyl group, an n-propoxyiminomethyl group, and an i-propoxyiminomethyl group. N-butoxyiminomethyl group, tert-butoxyiminomethyl group and the like, more preferably methoxyiminomethyl group.

In the above formula (1-6), v represents any integer of 1 to 4. If v is a 1, Y ¹⁰⁰ is added to any one of the six carbon atoms constituting the phenyl group (C). When v is 2 to 4, Y ¹⁰⁰ is added to any two, three or four of the carbon atoms (C).

In the above formula ^{(1-6), R 101a} and halogen atom represented by ^{R 102a} represents the same definition as above, _C 1 ~ _{C 6} alkyl substituted _C 1 may be ~ _{C 6} alkyl group by a halogen atom The group part includes 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, neopentyl group, 2 -Pentyl group, 3-pentyl group, tert-pentyl group, n-hexyl group, i-hexyl group, 2-hexyl group, 3-hexyl group and the like, more preferably methyl group or ethyl group .

In the above formula ^(1-6), as the _C 1 ~ _{C 4} alkoxy group moiety of ^{R 101a} and good _C 1 ~ _{C 4} alkoxy group optionally substituted by a halogen atom represented by ^{R 102a,} a methoxy group, an ethoxy group N-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, sec-butoxy group, tert-butoxy group and the like, more preferably methoxy group. Further, R ^101a and R ^102a on the same carbon atom can be each represented by (═O) or (═S) by being bonded to one oxygen atom or sulfur atom. R ^101a and R ^102a on the same carbon atom can be bonded at the same time to represent a C ₁ -C ₄ alkoxyimino group, such as a methoxyimino group. R ^101a and R ^102a on the same carbon atom can be bonded to each other to form a 3-membered ring, 4-membered ring, 5-membered ring or 6-membered ring with 2 to 5 alkylene groups.

In the above formula ^{(1-6), R 101b} and halogen atom represented by ^{R 102b} represents the same definition as above, _C 1 ~ _{C 6} alkyl substituted _C 1 may be ~ _{C 6} alkyl group by a halogen atom The group part includes 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, neopentyl group, 2 -Pentyl group, 3-pentyl group, tert-pentyl group, n-hexyl group, i-hexyl group, 2-hexyl group, 3-hexyl group and the like, more preferably methyl group or ethyl group .

In the above formula ^(1-6), as the _C 1 ~ _{C 4} alkoxy group moiety of the ^{R 101b} and good _C 1 ~ _{C 4} alkoxy group optionally substituted by a halogen atom represented by ^{R 102b,} a methoxy group, an ethoxy group N-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, sec-butoxy group, tert-butoxy group and the like, more preferably methoxy group.
In the above formula (1-6), u represents an integer of 0 or 1.

In the above formula (1-6), as the _C 2 ~ _{C 6} alkenyl moiety of the good _C 2 ~ _{C 6} alkenyl group optionally substituted by a halogen atom represented by ^{W 1,} 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 group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group And more preferably a 2-propenyl group.

In the above formula (1-6), as the _C 2 ~ _{C 6} alkynyl moiety of the good _C 2 ~ _{C 6} alkynyl group optionally substituted by a halogen atom represented by ^{W 1,} ethynyl, 1-propynyl, 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, etc., more preferably propargyl group Is mentioned.

In the above formula (1-6), the C ₃ to C ₆ cycloalkyl group represented by W ¹ includes a cyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, and 2,2-dimethylcyclo A propyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. are mentioned, More preferably, a cyclopropyl group is mentioned.

In the above formula (1-6), the C ₃ -C ₆ cycloalkyl C ₁ -C ₃ alkyl group represented by W ¹ includes a cyclopropylmethyl group, a 1-cyclopropylethyl group, a 2-cyclopropylethyl group 1-cyclopropylpropyl group, 2-cyclopropylpropyl group, 3-cyclopropylpropyl group, 1-cyclopropylbutyl group, 2-cyclopropylbutyl group, 3-cyclopropylbutyl group, 4-cyclopropylbutyl group, Examples thereof include a cyclobutylmethyl group, a 1-cyclobutylethyl group, a 2-cyclobutylethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a cycloheptylmethyl group, and a cyclooctylmethyl group, and more preferably a cyclopropylmethyl group. It is done.

In the above formula (1-6), as the _C 1 ~ _{C 6} alkyl group portion of the optionally substituted _C 1 ~ _{C 6} alkyl group by a halogen atom represented by ^{W 1,} an acetyl group, a propionyl group, A butyryl group, an i-butyryl group, a valeryl group, a pivaloyl group and the like can be mentioned, and an acetyl group is more preferred. The number of carbon atoms of the alkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1-6), as the _C 2 ~ _{C 6} alkenyl group moiety of the optionally substituted _C 2 be ~ _{C 6} alkenyl group by halogen atom represented by ^{W 1,} acryloyl group, methacryloyl group, etc. And more preferably an acryloyl group. The number of carbon atoms of the alkenylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1-6), as the _C 2 ~ _{C 6} alkynyl group moiety of the optionally substituted _C 2 be ~ _{C 6} alkynyl group with halogen atoms represented by ^{W 1,} Puropioriru group, Mechirupuropio A ryl group etc. are mentioned, A propioyl group is mentioned more suitably. The number of carbon atoms of the alkynylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1-6), as the _C 3 ~ _{C 6} cycloalkyl group moiety of the optionally substituted _C 3 be ~ _{C 6} cycloalkyl group with a halogen atom represented by ^{W 1,} cyclopropanecarbonyl group 1-methylcyclopropanecarbonyl group, 2-methylcyclopropanecarbonyl group, 2,2-dimethylcyclopropanecarbonyl group, cyclobutanecarbonyl group, cyclopentanecarbonyl group, cyclohexanecarbonyl group and the like, more preferably cyclopropane A carbonyl group is mentioned. The number of carbon atoms of the cycloalkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1-6), a C ₃ -C ₆ cycloalkyl C ₁ -C ₃ alkylcarbonyl group C ₃ -C ₆ cycloalkyl C ₁ -C optionally substituted with a halogen atom represented by W ¹ Examples of the _3- alkylcarbonyl group include cyclopropaneacetyl, cyclopropanepropionyl, 2-cyclopropaneacetyl, 1-methylcyclopropaneacetyl, 2-methylcyclopropaneacetyl, 2,2-dimethylcyclopropaneacetyl , Cyclobutane acetyl group, cyclopentane acetyl group, cyclohexane acetyl group, and the like, more preferably cyclopropane acetyl group. The number of carbon atoms of the cycloalkylalkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1-6), as the ^C 1 - ^{C 6} alkoxycarbonyl group portion - good ^C 1 optionally substituted by a halogen atom ^{C 6} alkoxycarbonyl group represented by ^{W 1,} a methoxycarbonyl group, an ethoxycarbonyl Group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, n-pentoxycarbonyl group, neopentoxycarbonyl group , 2-pentoxycarbonyl group, 3-pentoxycarbonyl group and the like, more preferably tert-butoxycarbonyl group. 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 (1-6), as the C _{2 ~} C ₆ alkenyloxycarbonyl group moiety of the optionally substituted C ₂ be _~ C ₆ alkenyloxycarbonyl group with a halogen atom represented by W ^1, vinyl oxycarbonyl group 1-propenyloxycarbonyl group, 2-propenyloxycarbonyl group, 1-butenyloxycarbonyl group, 2-butenyloxycarbonyl group, 3-butenyloxycarbonyl group and the like, more preferably vinyloxycarbonyl Groups. The number of carbon atoms of the alkenyloxycarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1-6), as the C _{2 ~} C ₆ alkynyloxy group moiety of the optionally substituted C ₂ be _~ C ₆ alkynyloxy group with the halogen atom represented by W ^1, ethynyl oxycarbonyl group 1-propynyloxycarbonyl group, propargyloxycarbonyl group, 1-butynyloxycarbonyl group, 2-butynyloxycarbonyl group, 3-butynyloxycarbonyl group, 1-methyl-2-propynyloxycarbonyl group, 2- Examples thereof include a methyl-3-butynyloxycarbonyl group, and a propargyloxycarbonyl group is more preferable. The number of carbon atoms of the alkynyloxycarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1-6), as the _C 3 ~ _{C 6} cycloalkyl alkyloxycarbonyl moiety of the optionally substituted _C 3 be ~ _{C 6} cycloalkyloxy group with a halogen atom represented by ^{W 1,} cyclopropyl Oxycarbonyl group, 1-methylcyclopropyloxycarbonyl group, 2-methylcyclopropyloxycarbonyl group, 2,2-dimethylcyclopropyloxycarbonyl group, cyclobutyloxycarbonyl group, cyclopentyloxycarbonyl group, cyclohexyloxycarbonyl group, etc. And a cyclopropyloxycarbonyl group is more preferable. The number of carbon atoms of the cycloalkyloxycarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1-6), a C ₃ -C ₆ cycloalkyl C ₁ -C ₃ alkyloxycarbonyl group C ₃ -C ₆ cycloalkyl C _1- which may be substituted with a halogen atom represented by W ^1- Examples of the C ₃ alkyloxycarbonyl group include cyclopropylmethyloxycarbonyl group, 1-methylcyclopropylmethyloxycarbonyl group, 2-methylcyclopropylmethyloxycarbonyl group, 2,2-dimethylcyclopropylmethyloxycarbonyl group, cyclo A butylmethyloxycarbonyl group, a cyclopentyloxymethylcarbonyl group, a cyclohexylmethyloxycarbonyl group, etc. are mentioned, More preferably, a cyclopropylmethyloxycarbonyl group is mentioned. The number of carbon atoms of the cycloalkylalkyloxycarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1-6), as the _C 1 ~ _{C 6} alkyl amino group moiety of the optionally substituted _C 1 ~ _{C 6} alkyl amino group with a halogen atom represented by ^{W 1,} methylaminocarbonyl group Ethylaminocarbonyl group, n-propylaminocarbonyl group, i-propylaminocarbonyl group, n-butylaminocarbonyl group, i-butylaminocarbonyl group, sec-butylaminocarbonyl group, tert-butylaminocarbonyl group, n- A pentylaminocarbonyl group etc. are mentioned, A methylaminocarbonyl group is mentioned more suitably. The number of carbon atoms of the alkylaminocarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1-6), as di _C 1 ~ _{C 6} alkyl amino group moiety of a substituted di _C 1 may be ~ _{C 6} alkyl amino group with a halogen atom represented by ^{W 1} is dimethylamino Carbonyl group, methylethylaminocarbonyl group, diethylaminocarbonyl group, di-n-propylaminocarbonyl group, methyl n-propylaminocarbonyl group, ethyl n-propylaminocarbonyl group, di-propylaminocarbonyl group, di-n-butylamino Examples thereof include a carbonyl group, a dii-butylaminocarbonyl group, a disec-butylaminocarbonyl group, a ditert-butylaminocarbonyl group, and more preferably a dimethylaminocarbonyl group. The number of carbon atoms of the dialkylaminocarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1-6), the C ₃ -C ₆ cycloalkylaminocarbonyl group of the C ₃ -C ₆ cycloalkylaminocarbonyl group which may be substituted with a halogen atom represented by W ¹ includes cyclopropyl Aminocarbonyl group, 1-methylcyclopropylaminocarbonyl group, 2-methylcyclopropylaminocarbonyl group, 2,2-dimethylcyclopropylaminocarbonyl group, cyclobutylaminocarbonyl group, cyclopentylaminocarbonyl group, cyclohexylaminocarbonyl group, etc. And a cyclopropylaminocarbonyl group is more preferable. The number of carbon atoms of the cycloalkylaminocarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1-6), a C ₃ to C ₆ cycloalkyl C ₁ to C ₃ alkylaminocarbonyl group C ₃ to C ₆ cycloalkyl C ₁ to C ₁ optionally substituted with a halogen atom represented by W ¹ Examples of the C ₃ alkylaminocarbonyl group include cyclopropylmethylaminocarbonyl group, 1-methylcyclopropylmethylaminocarbonyl group, 2-methylcyclopropylmethylaminocarbonyl group, 2,2-dimethylcyclopropylmethylaminocarbonyl group, cyclo A butylmethylaminocarbonyl group, a cyclopentylaminomethylcarbonyl group, a cyclohexylmethylaminocarbonyl group, etc. are mentioned, More preferably, a cyclopropylmethylaminocarbonyl group is mentioned. The number of carbon atoms of the cycloalkylalkylaminocarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

The formula (1-6), as the _C 1 - _{C 6} alkylsulfonyl group portion - good _C 1 optionally substituted by a halogen atom _{C 6} alkylsulfonyl group represented by ^{W 1,} methanesulfonyl group, ethanesulfonyl Group, n-propanesulfonyl group, i-propanesulfonyl group, n-butanesulfonyl group, i-butanesulfonyl group, sec-butanesulfonyl group, tert-butanesulfonyl group, n-pentanesulfonyl group, and the like. Includes a methanesulfonyl group.

In the above formula (1-6), as the C _{3 ~} C ₆ cycloalkyl sulfonyl group moiety of the optionally substituted C ₃ be _~ C ₆ cycloalkyl sulfonyl group with a halogen atom represented by W ^1, cyclopropanesulfonyl group 1-methylcyclopropanesulfonyl group, 2-methylcyclopropanesulfonyl group, 2,2-dimethylpropanesulfonyl group, cyclobutanecarbonyl group, cyclopentanecarbonyl group, cyclohexanecarbonyl group and the like, more preferably cyclopropanesulfonyl group Groups.

In the above formula (1-6), a C ₃ -C ₆ cycloalkyl C ₁ -C ₃ alkylsulfonyl group C ₃ -C ₆ cycloalkyl C ₁ -C optionally substituted with a halogen atom represented by W ¹ Examples of the _3- alkylsulfonyl group include cyclopropylmethylsulfonyl, 1-methylcyclopropylmethylsulfonyl, 2-methylcyclopropylmethylsulfonyl, 2,2-dimethylcyclopropylmethylsulfonyl, cyclobutylmethylsulfonyl, cyclopentyl A sulfonyl group, a cyclohexylmethylsulfonyl group, etc. are mentioned, More preferably, a cyclopropylmethylsulfonyl group is mentioned.

In the above formula (1-6), as the C _{1 ~} C ₆ alkylaminosulfonyl group moiety of the optionally substituted C _{1 ~} C ₆ alkylaminosulfonyl group with a halogen atom represented by W ^1, methylaminosulfonyl group Ethylaminosulfonyl group, n-propylaminosulfonyl group, i-propylaminosulfonyl group, n-butylaminosulfonyl group, i-butylaminosulfonyl group, sec-butylaminosulfonyl group, tert-butylaminosulfonyl group, n- A pentylaminosulfonyl group etc. are mentioned, A methylaminosulfonyl group is mentioned more suitably.

In the above formula (1-6), as di C _{1 ~} C ₆ alkylaminosulfonyl group moiety of a substituted di C ₁ may be _~ C ₆ alkylaminosulfonyl group with a halogen atom represented by W ¹ is dimethylamino Sulfonyl group, methylethylaminosulfonyl group, diethylaminosulfonyl group, di-n-propylaminosulfonyl group, methyl n-propylaminosulfonyl group, ethyl n-propylaminosulfonyl group, dii-propylaminosulfonyl group, di-n-butylamino Examples include a sulfonyl group, a dii-butylaminosulfonyl group, a disec-butylaminosulfonyl group, a ditert-butylaminosulfonyl group, and more preferably a dimethylaminosulfonyl group.

In the above formula (1-6), examples of the aryl group portion of the aryl group which may be substituted with a halogen atom represented by W ¹ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, and the like. A phenyl group is preferable.
In the above formula (1-6), examples of the arylcarbonyl group portion of the arylcarbonyl group which may be substituted with a halogen atom represented by W ¹ include a benzoyl group, a 1-naphthoyl group, and a 2-naphthoyl group. More preferred is a benzoyl group.

In the above formula (1-6), the aryloxycarbonyl group portion of the aryloxycarbonyl group which may be substituted with a halogen atom represented by W ¹ includes a phenoxycarbonyl group, a 1-naphthyloxycarbonyl group, and 2-naphthyl. An oxycarbonyl group etc. are mentioned, More preferably, a phenoxycarbonyl group is mentioned.
In the above formula (1-6), the arylaminocarbonyl group part of the arylaminocarbonyl group which may be substituted with a halogen atom represented by W ¹ includes a phenylaminocarbonyl group, a 1-naphthylaminocarbonyl group, 2- A naphthylaminocarbonyl group etc. are mentioned, A phenylaminocarbonyl group is mentioned more suitably.

In the above formula (1-6), examples of the arylsulfonyl group part of the optionally substituted arylsulfonyl group represented by W ¹ include a benzenesulfonyl group, a 1-naphthalenesulfonyl group, a 2-naphthalenesulfonyl group, and the like. More preferred is a benzenesulfonyl group. The halogen atom as a substituent has the same definition as above, and examples of the C ₁ -C ₃ alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, and the like, and more preferably a chlorine atom or A methyl group is mentioned.

In the above formula (1-6), as the _C 1 ~ _{C 6} alkyl group portion of the good _C 1 ~ _{C 6} alkyl group optionally substituted by a halogen atom represented by ^{W 2,} a methyl group, an ethyl group, n- Propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, neopentyl group, 2-pentyl group, 3-pentyl group, tert-pentyl group N-hexyl group, i-hexyl group, 2-hexyl group, 3-hexyl group and the like, and a methyl group is more preferable.

In the above formula (1-6), as the _C 2 ~ _{C 6} alkenyl moiety of the good _C 2 ~ _{C 6} alkenyl group optionally substituted by a halogen atom represented by ^{W 2,} a vinyl group, a 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 group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group And more preferably a 2-propenyl group.

In the above formula (1-6), as the _C 2 ~ _{C 6} alkynyl moiety of the good _C 2 ~ _{C 6} alkynyl group optionally substituted by a halogen atom represented by ^{W 2,} ethynyl, 1-propynyl, 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, etc., more preferably propargyl group Is mentioned.

In the above formula (1-6), the C ₃ -C ₆ cycloalkyl group represented by W ² includes a cyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, and 2,2-dimethylcyclo A propyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. are mentioned, More preferably, a cyclopropyl group is mentioned.
In the above formula (1-6), the C ₁ -C ₆ alkoxy C ₁ -C ₃ alkyl group represented by W ² includes a methoxymethyl group, an ethoxymethyl group, an n-propoxymethyl group, a methoxyethyl group, and the like. More preferably, a methoxymethyl group is mentioned.

In the above formula (1-6), as the _C 1 ~ _{C 6} alkyl group portion of the optionally substituted _C 1 ~ _{C 6} alkyl group by a halogen atom represented by ^{W 2,} an acetyl group, a propionyl group, A butyryl group, an i-butyryl group, a valeryl group, a pivaloyl group and the like can be mentioned, and an acetyl group is more preferred. The number of carbon atoms of the alkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.

In the above formula (1-6), as the _C 1 - _{C 6} alkoxycarbonyl group portion - good _C 1 optionally substituted by a halogen atom _{C 6} alkoxycarbonyl group represented by ^{W 2,} a methoxycarbonyl group, an ethoxycarbonyl Group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, n-pentoxycarbonyl group, neopentoxycarbonyl group , 2-pentoxycarbonyl group, 3-pentoxycarbonyl group and the like, more preferably tert-butoxycarbonyl group. 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.

The formula (1-6), as the _C 1 - _{C 6} alkylsulfonyl group portion - good _C 1 optionally substituted by a halogen atom _{C 6} alkylsulfonyl group represented by ^{W 2,} methanesulfonyl group, ethanesulfonyl Group, n-propanesulfonyl group, i-propanesulfonyl group, n-butanesulfonyl group, i-butanesulfonyl group, sec-butanesulfonyl group, tert-butanesulfonyl group, n-pentanesulfonyl group, and the like. Includes a methanesulfonyl group.

In the above formula (1-6), examples of the arylcarbonyl group portion of the arylcarbonyl group which may be substituted with a halogen atom represented by W ² include a benzoyl group, a 1-naphthoyl group, and a 2-naphthoyl group. More preferred is a benzoyl group.

In the above formula (1-6), the arylsulfonyl group moiety of the optionally substituted arylsulfonyl group represented by W ² includes a benzenesulfonyl group, a 1-naphthalenesulfonyl group, a 2-naphthalenesulfonyl group, and the like. More preferred is a benzenesulfonyl group. The halogen atom as a substituent has the same definition as above, and examples of the C ₁ -C ₃ alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, and the like, and more preferably a chlorine atom or A methyl group is mentioned.

Next, representative examples of the substituted phenyl ether compounds represented by the formula (1) are shown in Tables 1 to 8, and typical examples of the phenol compounds represented by the formula (2) are shown in Table 9. It is not limited. In addition, these compounds include compounds including optical isomers, E isomers, and Z isomers. The compound number is referred to in the following description.

Representative examples of N-substituted aniline compounds represented by formula (1-6) are shown in Tables 10 to 11, and typical examples of aniline compounds represented by formula (3) are shown in Table 12. It is not limited to compounds. In addition, these compounds include compounds including optical isomers, E isomers, and Z isomers. The compound number is 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, “Ac” represents an acetyl group, and “Bz” represents a benzoyl group. “H” represents a hydrogen atom. “On TLC” and “under TLC” indicate isomers.

Table 1 represents a specific example of the formula (1) in which q is 0 and p is 1, Table 2 represents a specific example of the formula (1) in which q is 0 and p is 2, and Table 3 Represents a specific example of the formula (1) in which q is 0 and p is 3, Table 4 represents a specific example of the formula (1) in which q is 0 and p is 4, and Table 5 represents the q Represents a specific example of the formula (1) in which 0 is 0 and p is 5, Table 6 represents a specific example of the formula (1) in which q is 1 and p is 2, and Table 7 shows that q is 1. Table 8 represents a specific example of Formula (1) in which q is 1 and p is 4, Table 9 represents a specific example of Formula (2). A specific example is shown. R ^1a , R ^1b , R ^1c , R ^1d , and R ^1e represent R ¹ specifying the substitution position on the alkylene chain, and R ^2a , R ^2b , R ^2c , R ^2d , and R ^2e are substitution positions on the alkylene chain R ^{2 in} which is specified.

Table 10 shows a specific example of formula (1-6) where u is 0, Table 11 shows a specific example of formula (1-6) where u is 1, and Table 12 shows a specific example of formula (3) Represents.

In the column “Ym” of these tables, for example, 3-F indicates that a fluorine atom is substituted at the 3-position of the phenyl group, and 3,4,5-F ₃ indicates the 3,4 of the phenyl group. , Indicating that a total of three fluorine atoms are substituted, one at the 5-position, and 2-F-4-Cl has a fluorine atom at the 2-position of the phenyl group and a chlorine atom at the 4-position. Indicates that

Among the compounds represented by the formula (1), compounds represented by the following formula (1-1) are preferable, and particularly preferred representative examples include compounds represented by the following formula (1-2).

(In Formula (1-1), n represents an integer of 0 or 1, X ² represents a fluorine atom, a chlorine atom, a bromine atom, or a cyano group, and R ^1a and R ^2a are each independently A fluorine atom, a hydroxyl group, an ethyl group, an isopropyl group, an isobutyl group, a methoxy group, an acetyloxy group, and R ^1a and R ^2a are bonded to one nitrogen atom to form a methoxyimino group (= NOMe). Or they can be bonded together to form a 3-membered or 5-membered ring.)

In formula (1-2), n represents an integer of 0 or 1, and X ² represents a fluorine atom or a chlorine atom.

The compound according to the present invention represented by the above formula (1) can be produced according to the production method shown below, but is not limited to these methods.

[Reaction step 1]

(In the above formula, A, X ¹ , X ² , Y, R ¹ , R ² , Z, m, p, q have the same meaning as the substituted phenyl ether compound represented by the above formula (1), and n is 1 or 2 is shown.)

The compound represented by the formula (1c) according to the present invention can be produced, for example, by reacting the compound represented by the above formula (1b) with an oxidizing agent.
Examples of the oxidizing agent used in this reaction include hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, OXONE (registered trademark, manufactured by EI DuPont; trade name; peroxohydrogensulfate Potassium-containing substances), N-chlorosuccinimide, N-bromosuccinimide, tert-butyl dichlorite, sodium hypochlorite, oxygen and the like. Preferred are m-chloroperbenzoic acid and hydrogen peroxide.

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, water and the like.

[Reaction step 2]

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

The compound represented by the formula (1) according to the present invention includes, for example, a compound represented by the above formula (2a) and a compound represented by the above formula (4) in the presence of a base, if necessary. It can manufacture by making it react in presence.

The raw material represented by the above formula (4) is known in some cases and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Or it can also manufacture easily from the reagent which can be obtained according to the well-known method as described in an 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, triethylamine, potassium hydroxide, sodium hydroxide and the like.

Examples of the catalyst used in this reaction include tetrabutylammonium bromide or tetrabutylammonium chloride.

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, sulfolane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; fats such as pentane, hexane, cyclohexane, cycloheptane Group hydrocarbons, water or a mixed solvent thereof. N, N-dimethylformamide, dichloromethane, or a mixture of water and an organic solvent is preferred.

[Reaction step 3]

(In the above formula, A, X ¹ , X ² , Y, R ¹ , R ² , Z, n, m, p, q have the same meaning as described above.)

The compound represented by the formula (1) according to the present invention is, for example, Bulletin of the Chemical Society of Japan, 1967, p. 936, Bulletin of the Chemical Society of Japan, 1967, p. According to the method described in 2380, the compound represented by the above formula (2a) and the compound represented by the above formula (5) can be produced by Mitsunobu reaction.

The raw material represented by the above formula (5) is known in some cases and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Or it can also manufacture easily from the reagent which can be obtained according to the well-known method as described in an experimental chemistry course, Organic Synthesis, etc.

Examples of the phosphorus compound used in this reaction include triphenylphosphine, tri-n-butylphosphine, tritert-butylphosphine, phenoxydiphenylphosphine, and the like. Preferred are triphenylphosphine and phenoxydiphenylphosphine.

Examples of the azodicarboxylic acid ester used in this reaction include diethyl azodicarboxylate and diisopropyl azodicarboxylate. Preferred is diethyl azodicarboxylate.

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 is tetrahydrofuran.

[Reaction step 4]

(In the above formula, X ³ represents a halogen atom, and A, X ¹ , Y, R ¹ , R ² , Z, n, m, p, q have the same meaning as described above.)

The compound represented by the formula (1e) according to the present invention can be produced, for example, by reacting the compound represented by the above formula (1d) 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 chlorine, bromine, iodine, sulfuryl chloride and the like.

The solvent used in this reaction is, for example, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, or a mixed solvent thereof. Preferred is dichloromethane.

[Reaction step 5]

(In the above formula, PG represents a protecting group such as an alkylcarbonyl group, a haloalkylcarbonyl group, an arylcarbonyl group, and an alkoxycarbonyl group, and X ¹ , X ² , and L have the same meaning as described above.)

The starting material represented by the above formula (6) is a known compound and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc.

The production intermediate represented by the above formula (8) is obtained by converting the compound represented by the above formula (6) and the compound represented by the above formula (7) into a base as in the above reaction step 5-1. It can be produced by reacting in the presence.

Examples of the base used in the reaction step 5-1 include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine and the like. Preferred is triethylamine.

Examples of the solvent used in the reaction step 5-1 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 and cycloheptane; water or a mixed solvent thereof. Preferred is dichloromethane.

The production intermediate represented by the above formula (9) comprises, as in the above reaction step 5-2, a compound represented by the above formula (8) obtained in the above reaction step 5-1, and chlorosulfonic acid. It can be produced by reacting. Further, the production intermediate represented by the above formula (9) is prepared by reacting the fuming sulfuric acid with the compound represented by the above formula (8) obtained in the above reaction step 5-1, and then in the presence of a base. It can be produced by reacting with diphosphorus pentoxide.

Examples of the base used in the reaction step 5-2 include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine and the like. Preferred is potassium carbonate.

The production intermediate represented by the above formula (10) includes a compound represented by the above formula (9) obtained by the above reaction step 5-2, a metal and an acid, as in the above reaction step 5-3. It can be produced by reduction using lithium aluminum hydride or red phosphorus, iodine and an acid.

Examples of the metal used in the reaction step 5-3 include zinc, tin, iron, and nickel. Zinc and tin are preferable.

Examples of the acid used in the reaction step 5-3 include hydrochloric acid, sulfuric acid, and acetic acid. Preferred are hydrochloric acid, acetic acid and the like.

The production intermediate represented by the above formula (11) is obtained by reacting the compound represented by the above formula (10) obtained by the above reaction step 5-3 with the acid or base as in the above reaction step 5-4. It can manufacture by hydrolyzing using.

Examples of the acid used in the reaction step 5-4 include hydrochloric acid, sulfuric acid, acetic acid and the like. Preferred are hydrochloric acid, acetic acid and the like.

Examples of the base used in the reaction step 5-4 include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, triethylamine, diisopropylethylamine, pyridine and the like. Sodium hydroxide, potassium hydroxide and the like are preferable.

[Reaction step 6]

(In the above formula, A, L, X ¹ and X ² have the same meaning as described above.)

The compound represented by the formula (2b) according to the present invention includes, for example, a production intermediate represented by the formula (11) obtained by the reaction step 5 and a compound represented by the formula (12). , And in the presence or absence of Rongalite (Rongalite, trade name of BASF; sodium hydroxymethanesulfinate dihydrate). Moreover, it can also manufacture by making it react in presence of a catalyst as needed.

The raw material represented by the above formula (12) is known in some cases and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Or it can also manufacture easily from the reagent which can be obtained according to the well-known method as described in an experimental chemistry course, Organic Synthesis, etc.

The amount of the raw material represented by the formula (12) used here may be appropriately selected from the range of 1 to 5 mol with respect to 1 mol of the compound represented by the formula (11). 0 to 2.0 moles.

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

The amount of the base used here may be appropriately selected from the range of 0 to 5 mol, preferably 0 to 2.0 mol, per 1 mol of the compound represented by the formula (11).

Examples of the catalyst used in this reaction include tetrabutylammonium bromide or tetrabutylammonium chloride.
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, sulfolane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; fats such as pentane, hexane, cyclohexane, cycloheptane Group hydrocarbons, water or a mixed solvent thereof. N, N-dimethylformamide or a mixture of water and an organic solvent is preferred.

The amount of the solvent used may be appropriately selected from the range of 0.1 to 100 liters with respect to 1 mol of the compound represented by the formula (11), and preferably 1.0 to 5.0 liters.

The reaction temperature may be selected from an arbitrary range from −30 ° C. to the reflux temperature in the reaction system, and preferably from 0 ° C. to 150 ° C.

The reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is preferably in the range of 10 minutes to 20 hours.

[Reaction step 7]

(In the above formula, A, X ¹ and X ² have the same meaning as described above, and n represents 1 or 2.)

The compound represented by the formula (2c) according to the present invention can be produced, for example, by reacting the compound represented by the above formula (2b) with an oxidizing agent.

Examples of the oxidizing agent used in this reaction include hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, OXONE (registered trademark, manufactured by EI DuPont; trade name; peroxohydrogensulfate Potassium-containing substances), N-chlorosuccinimide, N-bromosuccinimide, tert-butyl dichlorite, sodium hypochlorite, oxygen and the like. Preferred are m-chloroperbenzoic acid and hydrogen peroxide.

The amount of the oxidizing agent used here may be appropriately selected from the range of 1.0 to 6.0 mol, preferably 1.0 to 2 with respect to 1 mol of the compound represented by the formula (2b). 0.0 mole.

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, water, methanol, ethanol and the like.

The amount of the solvent used may be appropriately selected from the range of 0.1 to 100 liters, preferably 1.0 to 5.0 liters, per 1 mol of the compound represented by the formula (2b).

The reaction temperature may be selected from an arbitrary range from −30 ° C. to the reflux temperature in the reaction system, and preferably from −10 ° C. to 50 ° C.

Further, the compound according to the present invention represented by the formula (1-6) can be produced according to the production methods shown below, but is not limited to these methods.

[Reaction step 8]

(In the above formula, A ¹⁰⁰ , X ¹⁰¹ , X ¹⁰² , Y ¹⁰⁰ , R ^101a , R ^102a , R ^101b , R ^102b , W ¹ , W ² , v, u are represented by the above formula (1-6). The same meaning as the N-substituted aniline compound is shown, and n represents 1 or 2.)

The compound represented by the formula (1-6b) according to the present invention can be obtained, for example, by reacting the compound represented by the above formula (1-6a) with an oxidizing agent in the presence of a catalyst as necessary. Can be manufactured.
Examples of the oxidizing agent used in this reaction include hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, OXONE (registered trademark, manufactured by EI Dupont); ), N-chlorosuccinimide, N-bromosuccinimide, tert-butyl dichlorite, sodium hypochlorite, oxygen and the like. Preferred are m-chloroperbenzoic acid and hydrogen peroxide.

Examples of the catalyst used in this reaction include molybdenum oxide, boric acid, tris (acetylacetone) iron, and the like. Preferred is molybdenum oxide.
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, water and the like.

[Reaction step 9]

(In the above formula, L ¹⁰⁰ represents a leaving group such as a halogen atom, an alkylsulfonyloxy group, a haloalkylsulfonyloxy group, an arylsulfonyloxy group, etc., and represents A ¹⁰⁰ , X ¹⁰¹ , X ¹⁰² , Y ¹⁰⁰ , R ^101a , R ^102a. , R ^101b , R ^102b , W ¹ , W ² , v, and u have the same meaning as described above, and n represents an integer of 0 to 2.)

The compound represented by the formula (1-6) according to the present invention includes, for example, a compound represented by the above formula (13) and a compound represented by the above formula (14) in the presence of a base as necessary. It can be produced by reacting in the presence of a catalyst.
The raw material represented by the above formula (14) is known in some cases, and a commercially available product can be used. Or it can also manufacture easily according to the well-known method as described in an experimental chemistry course, Organic Synthesis, etc. from an available reagent.

Examples of the base used in this reaction include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine and the like. Of the base. Preferred are potassium carbonate, triethylamine, potassium hydroxide, sodium hydroxide and the like.
Examples of the catalyst used in this reaction include tetrabutylammonium bromide or tetrabutylammonium chloride.

[Reaction step 10]

(In the above formula, A ¹⁰⁰ , X ¹⁰¹ , X ¹⁰² , Y ¹⁰⁰ , R ^101a , R ^102a , R ^101b , R ^102b , W ¹ , W ² , n, v, and u have the same meanings as described above).

The compound represented by formula (1-6) according to the present invention is, for example, Bulletin of the Chemical Society of Japan, 1967, p. 936, Bulletin of the Chemical Society of Japan, 1967, p. According to the method described in 2380, the compound represented by the above formula (13) and the compound represented by the above formula (15) can be produced by Mitsunobu reaction.

The raw material represented by the above formula (15) is known in some cases, and a commercially available product can be used. Or it can also manufacture easily from the reagent which can be obtained according to the well-known method as described in an experimental chemistry course, Organic Synthesis, etc.

Examples of the phosphorus compound used in this reaction include triphenylphosphine, tri-n-butylphosphine, tritert-butylphosphine, phenoxydiphenylphosphine, and the like. Preferred are triphenylphosphine and phenoxydiphenylphosphine.
Examples of the azodicarboxylic acid ester used in this reaction include diethyl azodicarboxylate and diisopropyl azodicarboxylate. Preferred is diethyl azodicarboxylate.

[Reaction step 11]

(In the above formula, X ¹⁰³ represents a halogen atom, and A ¹⁰⁰ , X ¹⁰¹ , Y ¹⁰⁰ , R ^101a , R ^102a , R ^101b , R ^102b , W ¹ , W ² , n, v, and u have the same meaning as described above. Is shown.)

The compound represented by the formula (1-6d) according to the present invention is obtained by, for example, reacting the compound represented by the above formula (1-6c) with a halogenating agent in the presence of a catalyst as necessary. Can be manufactured.
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 chlorine, bromine, iodine, sulfuryl chloride and the like.

Examples of the catalyst used in this reaction include aluminum chloride and phenyl sulfide. Aluminum chloride is preferred.
Examples of the solvent used in this reaction include halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, carbon tetrachloride, acetic acid, and mixed solvents thereof. Preferred is dichloromethane.

[Reaction step 12]

(In the above formula, PG ¹⁰⁰ represents a protecting group such as an alkylcarbonyl group, a haloalkylcarbonyl group, an arylcarbonyl group, or an alkoxycarbonyl group, and X ¹⁰¹ , X ¹⁰² , and L ¹⁰⁰ have the same meaning as described above.)

The starting material represented by the above formula (16) is a known compound, and a commercially available product can be used.
The production intermediate represented by the above formula (18) is obtained by converting a compound represented by the above formula (16) and a compound represented by the above formula (17) into a base as in the above reaction step 12-1. It can be produced by reacting in the presence.

Examples of the base used in the reaction step 12-1 include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropyl. Ethylamine, pyridine and the like. Sodium hydroxide, potassium hydroxide, triethylamine and the like are preferable.

Examples of the solvent used in the reaction step 12-1 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 and cycloheptane; water or a mixed solvent thereof. Preferred is dichloromethane or a mixture of water and an organic solvent.

The production intermediate represented by the above formula (19) comprises, as in the above reaction step 12-2, a compound represented by the above formula (18) obtained in the above reaction step 12-1 and chlorosulfonic acid. It can be produced by reacting. The production intermediate represented by the above formula (19) is produced by reacting fuming sulfuric acid with the compound represented by the above formula (18) and then reacting with diphosphorus pentoxide in the presence of a base. can do.

Examples of the base used in the reaction step 12-2 include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine and the like. Preferred is potassium carbonate.
The production intermediate represented by the above formula (20) includes a compound represented by the above formula (19) obtained by the above reaction step 12-2, a metal and an acid, as in the above reaction step 12-3. It can be produced by reduction using lithium aluminum hydride or red phosphorus, iodine and an acid.

Examples of the metal used in the reaction step 12-3 include zinc, tin, iron, and nickel. Zinc and tin are preferable.
Examples of the acid used in the reaction step 12-3 include hydrochloric acid, sulfuric acid, and acetic acid. Preferred are hydrochloric acid, acetic acid and the like.
The production intermediate represented by the above formula (21) comprises a compound represented by the above formula (20) obtained by the above reaction step 12-3, an acid or a base, as in the above reaction step 12-4. It can manufacture by hydrolyzing using.

Examples of the acid used in the reaction step 12-4 include hydrochloric acid, sulfuric acid, acetic acid and the like. Preferred are hydrochloric acid, acetic acid and the like.
Examples of the base used in the reaction step 12-4 include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, triethylamine, diisopropylethylamine, pyridine and the like. Sodium hydroxide, potassium hydroxide and the like are preferable.

[Reaction step 13]

(In the above formula, A ¹⁰⁰ , L ¹⁰⁰ , X ¹⁰¹ , and X ¹⁰² have the same meaning as described above.)

The compound represented by the above formula (23) is obtained by, for example, converting the production intermediate represented by the above formula (21) obtained by the reaction step 12 and the compound represented by the above formula (22) into a base. It can be produced by reacting in the presence and absence of Rongalite (Rongalite, manufactured by BASF; sodium hydroxymethanesulfinate dihydrate). Moreover, it can also manufacture by making it react in presence of a catalyst as needed.

The raw material represented by the above formula (22) is known in some cases, and a commercially available product can be used. Or it can also manufacture easily from the reagent which can be obtained according to the well-known method as described in an experimental chemistry course, Organic Synthesis, etc.

Examples of the base used in this reaction include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine, sodium hydroxide, potassium hydroxide and the like. It is. Preferred is potassium carbonate.
Examples of the catalyst used in this reaction include tetrabutylammonium bromide or tetrabutylammonium chloride.

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, sulfolane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; fats such as pentane, hexane, cyclohexane, cycloheptane Group hydrocarbons, water or a mixed solvent thereof. N, N-dimethylformamide or a mixture of water and an organic solvent is preferred.

[Reaction step 14]

(In the above formula, A ¹⁰⁰ , X ¹⁰¹ , and X ¹⁰² have the same meaning as described above, and n represents 1 or 2.)

The compound represented by the above formula (24) can be produced, for example, by reacting the compound represented by the above formula (23) with an oxidant in the presence of a catalyst as necessary.
Examples of the oxidizing agent used in this reaction include hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, OXONE (registered trademark, manufactured by EI Dupont); ), N-chlorosuccinimide, N-bromosuccinimide, tert-butyl dichlorite, sodium hypochlorite, oxygen and the like. Preferred are m-chloroperbenzoic acid and hydrogen peroxide.
Examples of the catalyst used in this reaction include molybdenum oxide, boric acid, tris (acetylacetone) iron, and the like. Preferred is molybdenum oxide.

[Reaction step 15]

(In the above formula, Y ¹⁰⁰ , W ³ , W ⁴ , R ¹⁰³ , and v have the same meaning as described above.)

The compound represented by the formula (27) according to the present invention is, for example, Tetrahedron, 2011, p. According to the method described in 2323 and the like, it can be produced by Fenton reaction of the compound represented by the above formula (25).

The raw materials represented by the above formulas (25) and (26) are known in some cases and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Or it can also manufacture easily according to the well-known method as described in an experimental chemistry course, Organic Synthesis, etc. from an available reagent.
Examples of the peroxide used in this reaction include hydrogen peroxide, hydrogen peroxide-urea complex, tert-butyl peroxide, and peracetic acid. Preferred is hydrogen peroxide.

The catalyst used in this reaction is, for example, iron (II) sulfate, iron (II) ammonium sulfate, iron (II) tetrafluoroborate, iron (II) chloride, iron (II) bromide, iron iodide (II). ), Iron (II) acetate, iron (II) oxalate, bis (acetylacetonato) iron (II), ferrocene, and the like. Preferred is ferrocene.
Examples of the solvent used in this reaction include aprotic polar solvents such as dimethyl sulfoxide, diethyl sulfoxide, dipropyl sulfoxide, diisopropyl sulfoxide, diphenyl sulfoxide, and methylphenyl sulfoxide, or a mixed solvent thereof. Preferred is dimethyl sulfoxide.

[Reaction step 16]

The compound represented by the formula (28) according to the present invention is described in, for example, Chemical and Pharmaceutical Bulletin, 1999, p. According to the method described in 1013 and the like, the compound represented by the above formula (28) and the compound represented by the formula (26) can be produced by a coupling reaction in the presence of copper.
The raw material represented by the above formula (28) is known in some cases, and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Or it can also manufacture easily according to the well-known method as described in an experimental chemistry course, Organic Synthesis, etc. from an available reagent.
Examples of the solvent used in this reaction include aprotic polar solvents such as dimethyl sulfoxide, diethyl sulfoxide, dipropyl sulfoxide, diisopropyl sulfoxide, diphenyl sulfoxide, and methylphenyl sulfoxide, or a mixed solvent thereof. Preferred is dimethyl sulfoxide.

[Reaction step 17]

(In the above formula, Y ¹⁰⁰ , W ³ , W ⁴ and v have the same meaning as described above.)

The compound represented by the formula (29) according to the present invention can be produced by reducing the compound represented by the above formula (27).
Examples of the reducing agent used in this reaction include sodium borohydride, lithium aluminum hydride, diisobutylaluminum hydride, and the like. Preferred is sodium borohydride.
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; alcohols such as methanol, ethanol and isopropyl alcohol; dichloromethane and chloroform Halogenated hydrocarbons such as 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and cycloheptane; water or a mixed solvent thereof. Preferred is tetrahydrofuran.

[Reaction step 18]

(In the ^{formula, R 104 'indicates} which may _C 1 ~ _{C 4} alkylsulfonyl group which may or _C 1 ~ _{C 4} alkyl optionally substituted arylsulfonyl group, substituted with a halogen ^{atom, Y 100,} W ³ , W ⁴ , v, and L ¹⁰⁰ have the same meaning as described above.)

The compound represented by the formula (31) according to the present invention is produced, for example, by reacting the compound represented by the above formula (29) and the compound represented by the above formula (30) in the presence of a base. be able to.
Examples of the base used in this reaction include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine and the like. Of the base. 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, sulfolane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; fats such as pentane, hexane, cyclohexane, cycloheptane Group hydrocarbons, water or a mixed solvent thereof. Preferred is dichloromethane.

[Reaction step 19]

(In the above formula, W ^{3 ′} and W ^{4 ′} are each independently substituted with a C ₁ -C ₆ alkylcarbonyl group, a C ₁ -C ₆ alkoxycarbonyl group, or a halogen atom, which may be substituted with a halogen atom. A C ₁ -C ₆ alkylsulfonyl group which may be substituted, and Y ¹⁰⁰ , v, G and L ¹⁰⁰ have the same meaning as described above.)

The compound represented by the formula (34) according to the present invention is produced, for example, by reacting the compound represented by the above formula (32) and the compound represented by the above formula (33) in the presence of a base. be able to. Furthermore, the compound represented by the formula (36) according to the present invention is produced, for example, by reacting the compound represented by the above formula (34) and the compound represented by the above formula (35) in the presence of a base. can do.
Examples of the base used in this reaction include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine and the like. Of the base. 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, sulfolane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; fats such as pentane, hexane, cyclohexane, cycloheptane Group hydrocarbons, water or a mixed solvent thereof. Preferred is dichloromethane.

In any of the reactions from Reaction Step 1 to Reaction Step 19, the target compound can be obtained by performing ordinary operations in organic synthesis such as extraction, drying, concentration, and purification after completion of the reaction.

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

The substituted phenyl ether compound according to the present invention is not limited to the above production method, and can be produced by any organic synthesis technique.

Moreover, this invention compound can exhibit the outstanding control activity with respect to a wide range of insects, mites, crustaceans, molluscs, and nematodes. The compound of the present invention exhibits excellent control activity especially against insects and mites.
Among the compounds of the present invention, the compound represented by the above formula (1-1) is preferable because it exhibits a very excellent control activity against mites. Furthermore, the compound represented by the above formula (1-2) is particularly preferable because it has excellent residual effect to maintain the control activity against mites even after spraying. In addition, the compound represented by the above formula (1-2) is excellent in safety from oral administration tests on mice. Specific examples of the organism in which the compound of the present invention exhibits a controlling activity include the following.

For example, as insects, stigma Yamatosimi (Ctenolepisma villosa), sima (Lepisma saccharina), madara shimi (Thermobia domestica), etc.
Cockroaches (Periplaneta americana), Black cockroaches (Periplaneta furiginosa), Japanese cockroaches (Periplaneta japonica), German cockroaches (Blatella germanicat)
American termites (Incitermes minor), termites (Coptothermes formosanus), termites (Reticulitermes supertus), Taito termites (Odontotermes formosanus), etc.
Grasshopper (Ruspolia lineosa), Enma cricket (Teleoglyllus emma), Kera (Gryllotalpa orientalis), Tonosama locust (Locusta migratoria), Kobaneigo (Ezoa)
Chathamate (Trogium pulsatorium), Hiratachate (Liposcelis bostrychofila), Usgro chatter (Liposcelis corrodens), etc.
Chrysanthemum chicks (Lipeurus caponis), chicks (Menacanthus stramineus), bull lice (Damalinia bovis), horse lice (Damalinia caprae), etc.
Louseed cattle lice (Haematopinus eurosternus), swine lice (Haematopinus suis), louse lice (Pediculus humanus capitis), head lice (Pediculus humus pus), thrips pi
Thysanoptera of 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), Minami thrips ( Thrips palmi, Thrips tabaci, Hemithrips aculatus, Phytothrips diospyros i) etc.
Hemiptera of the 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 distinctissima) , Citrus leafworm (Diaphorina citri), grape aphid (Viteus vitifoliae), pea aphid (Acyrthosiphon pisum), bean aphid (Aphis craccivora), cotton aphid (Aphis gossypii), Aphis pomi, Aphis spiraecola, phia aphis, Aphicorthum irani, pteraria eus Peach Aphid (Myzus persicae), Wheat Beetle Rhinoceros (Rhopalosiphum padi), Wheat Midge Aphid (Schizophis graminum), Schizophis piricola (Toxa), Aphid terridium (Tax) 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 (Drosicha corpulenta) , Icerya purchasi, Prunococcus citri, Planococcus kraunhiae, 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-spotted stink bug (Creontiades coloripes), Trigotylus caestierium, Stephanitis nasti, Stephanitis pyrioides, Tohoku Shirahoshi stink 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 green stink bug (Nezara viridula), Chabae green bug (Plautia rossota stalei), Kambachabanagamekamemushi (Cavelerius saccharivorus), Kobanebane katsura (Togo hempterus), Spider helicopterin nissis), R. rottorus clavatus, Coleus puntigger, Rhopalus mculatus, Chimex lectularis, etc.
Coleoptera of 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), Tobiiromuna Boletus (Agriotes ogurae fuscicollis), White-headed click (Ectinus sericeus sericeus), Marubitus forumni fortum (Tobacco) Banmushi (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 beetle (Tribolium castaneum ), Anophorora malasiaca, Monochmus alternada endai, Xylotrechus pyrrhoderus, Azukizo Musi (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 (Diabrotica spp.), Colorado potato beetle (Leptinotarsa decemlineata), Rice beetle (Oulema oryzae), Kinojin beetle (Phyllotetta striolata), Arimodoki weevil (Cyl) s 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), maize weevil (Sitophilus zeamais), Shibao weevil (Sphenophrus venatus vestitus), pine beetle (Tomicus piniperda), slatted beetle (Lyctus brunneus), etc.,
Fleas (Ceraphyllus gallinae), dog fleas (Ctenocephalides canis), cat flea (Ctenocephalides felis), chicken fleas (Echinidophaga gallinacea), human fleas (X)
Diptera of 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), oriental fruit fly ( Bactrocera dorsalis, Agromyza oryzae, Namoguri flies (Chromatomya horticola), Liriomyza huidobrensis, Tomatoes Liriomyza sativae), legume leafminer (Liriomyza trifolii), onion maggot (Delia antiqua), seedcorn maggot (Delia platura), housefly (Musca domestica), such as the stable fly (Stomoxys calcitrans),
Lepidoptera of the smaller tea tortrix (Adoxophyes honmai), apple Coca summer fruit tortrix (Adoxophyes orana fasciata), Mi someone summer fruit moth (Archips fuscocupreanus), codling moth (Cydia pomonella), oriental fruit moth (Grapholita molesta), Chahamaki (Homona magnanima), soybean pod borer, Leguminivora glycinivorella (Leguminivora glycinivorella), Pandemis heparana, Tinea translucens, Prunus serrata, Lyonetia pelinella pelaribell 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 triannulellum), Cotton beetle (Pectinophora gossypiella), Peachinosaigai (Carposina sasakii), Chilo supressalis, Cnapha ocrocis medinalisa, Conogethes puntiferalis, Hyla unipais (Hellula undalis), Eustonia furnalis, European corn borer (Ostrilia peach). White butterfly (Pieris rapae crucivora), Ichimon seiseri (Parnara gutata guttata), Artemisia dasak (Ascotis selenaria), Chadokuga (Arna pseudoconsperga) ), 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, Mythimna separata, Naranga aenescens, Spodoptera exigua, Spodopter ur spo
Hymenoptera of 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), etc. Is mentioned.

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 (Haephysalis campanulata), Haephaphysalis longicornis, yamato tick (Ixodes ovadus tick) s persulcatus), 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 ), Mite mite (Demodex cati), rice mite (Oligonychus shinkajii), citrus mite mite (Pananychus citri), mallow mite (Pananychus mori) , Ringohadani (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 mite (Aculus schlechtendali), tea rust mite (Calacarus carinatus), prickly pear mite (Epitrimerus piri), green rust mite (Eriophy) es chibaensis), Citrus last mite (Phyllocoptruta oleivora), Robin tick (Rhizoglyhus robini), Typhophagus putresceniae (Tyrophagus pestenicus tick). ), 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.

As the crustaceans, the Obidu depts (Oxidus gracilis), etc.
Isopods such as Armadillium vulgare,
Ten-legged American crayfish (Procambarus clarkii),
For example, Boletiella hortensis.

As mollusks, primordial string eyes, such as Pomacea canalicula,
Examples include pulmonary African mussel (Achatina falica), slug (Meghiatum bilineatum), chakoura slug (Lehmannina valentiana), and Usuka westmai (Acusta specta sieboldiana).
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), Oxalic (Aphelenchoides besseyi), horn 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.

The compound of the present invention can be used as an active ingredient of agricultural and horticultural pest control agents. For formulation, suitable carriers, surfactants, fluidity improvers, bindings described in the Agricultural Chemicals Formulation Guide (edited by: Japanese Society for Agricultural Chemicals Application Methods, published by Japan Society for Plant Protection, 1997) You may mix | blend an agent, a thickener, antiseptic | preservative, etc.

In addition, an auxiliary agent may be blended in the formulation.

The agricultural and horticultural pest control agent containing the compound of the present invention can be formulated into any dosage form generally used as a dosage form for agricultural and horticultural pest control agents. 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.

For example, mineral carriers (kaolin, bentonite, clay, montmorillonite, talc, vermiculite, gypsum, diatomaceous earth, white clay, calcium carbonate, white carbon, quartz sand, ammonium sulfate, urea, etc.), vegetable powder (crystalline cellulose, etc.) ), Polymer compounds (petroleum resin, etc.), alumina, silicates, sugar polymers and the like.

Liquid carriers include water, alcohols (methanol, ethanol, n-propanol, ethylene glycol, glycerin, etc.), ethers (diethyl ether, tetrahydrofuran, 1,4-dioxane, cellosolve, etc.), ketones (methyl ethyl ketone, Cyclohexanone, etc.), esters (ethyl acetate, butyl acetate, fatty acid glycerin ester, etc.), nitriles, sulfoxides (dimethyl sulfoxide, etc.), alcohol ethers (ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, etc.), aliphatic or Alicyclic hydrocarbons (kerosene, kerosene, cyclohexane, etc.), aromatic hydrocarbons (benzene, toluene, xylene, solvent naphtha, methylnaphthalene, etc.), petroleum fractions, etc. It is.

Further, in the formulation, a surfactant can be blended for the purposes of emulsification, dispersion, solubilization, wetting, foaming, lubrication, spreading, spreading, and disintegration. Such surfactants include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkyl esters, polyoxyethylene alkyl phenyl ethers, polyoxyethylene aryl phenyl ethers, polyoxyethylene sorbitan alkyl esters, sorbitans). Alkyl esters, polyoxyethylene alkylene glycols, polyoxyethylene-polyoxypropylene block polymers, etc.), anionic surfactants (alkyl benzene sulfonates, alkyl naphthalene sulfonates, lignin sulfonates, alkyl sulfosuccinates, alkyls) Sulfate, polyoxyethylene alkyl sulfate, aryl sulfonate, polyoxyalkylene alkyl ether phosphate ester, polyoxy Siethylene alkyl ether phosphates, polycarboxylates, etc.), cationic surfactants (alkylamines such as laurylamine, stearyltrimethylammonium chloride, alkyldimethylbenzylammonium chloride, polyoxyethylene alkylamines, etc.) ), Amphoteric surfactants (dialkylaminoethyl betaine, alkyldimethylbenzyl betaine, etc.), but are not limited to these examples.

Further, examples of the fluidity improver include isopropyl phosphate ester and calcium stearate. Binders include methylcellulose, carboxymethylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, starch, carboxymethyl starch, dextrin, pullulan, sodium alginate, mannan, pectin, tragacanth gum, mannitol, sorbitol, propylene glycol alginate, guar gum Locust bean gum, gum arabic, xanthan gum, gelatin, casein, polyvinyl alcohol, polyethylene oxide, polyethylene glycol, ethylene / propylene block polymer, sodium polyacrylate, polyvinyl pyrrolidone, calcium lignin sulfonate and the like. Examples of thickeners include guar gum, xanthan gum, tragacanth gum, casein, dextrin, colloidal hydrous aluminum silicate, colloidal hydrous magnesium silicate, colloidal hydrous aluminum silicate, carboxymethylcellulose, polyvinyl alcohol and water-soluble cellulose ether. It can be illustrated. Examples of preservatives include sodium benzoate, potassium sorbate, p-chloro-metaxylenol, butyl p-oxybenzoate and 1,2-benzisothiazolin-3-one.

The content of the compound of the present invention can be appropriately selected depending on the dosage form of the preparation and the method of use. In general, the preferable content is in the range of 0.0001 to 90% by weight based on the total amount of the preparation.

For example, in the case of a powder, it is usually 0.01 to 50% by weight, preferably 0.05 to 20% by weight, based on the total amount of the preparation. 0.01 to 90% by weight, preferably 0.1 to 60% by weight. In the case of an emulsion, it is usually 0.01 to 80% by weight, preferably 0.1 to 70% by weight based on the total amount of the preparation. If it is a flowable agent, it is usually 0.01 to 60% by weight, preferably 0.1 to 50% by weight, based on the total amount of the formulation. The range is usually 0.01 to 50% by weight, preferably 0.1 to 20% by weight.

When the compound of the present invention is used as an agricultural or horticultural pest control agent, a bactericidal agent (a fungicide, a bactericidal agent, an antiviral agent, a plant resistance inducer), at the time of formulation or spraying, if necessary. Mix with one or more optional ingredients selected from insecticides, acaricides, nematicides, herbicides, bird repellents, growth regulators, fertilizers, soil conditioners, etc., or mix with tank mix when spraying It may be applied.

Of the above optional components, representative examples of fungicides, insecticides, acaricides and nematicides are shown below, but are not limited thereto.
Fungicide:
(1) Copper agent: Basic copper chloride, basic sulfur copper, cupric hydroxide, copper sulfate, oxine-copper, nonylphenol sulfone Copper (copper nonylphenol sulfate), DBEDC, etc.

(2) Inorganic fungicide Sulfur (sulfer), lime sulfur compound (sodium hydrogen carbonate), potassium hydrogen carbonate (potassium hydrogen carbonate), metallic silver (silver) and the like.

(3) Organic sulfur fungicide ziram, manneb, mancozeb, ambam, polycarbamate, propineb, thiuram, thiazine, india zineb).

(4) Organophosphorus fungicides IBP, EDDP, tolcrofos-methyl, pyrazophos, fosetyl-alminium and the like.

(5) Benzimidazole fungicides Carbendazim, thiabendazole, thiophanate-methyl, benomyl and the like.

(6) Dicarboximide fungicides iprodione, procymidone, vinclozolin and the like.

(7) Carboxamide fungicides oxycarboxin, carboxin, mepronil, flutolanil, boscalid, fluopyram, furamethizmza Penthiopyrad, bixafen, penflufen, fluxapyroxad, isopyrazam, tolfenpyrad, sedaxane, etc.

(8) Phenylamide fungicides Metalaxyl, metalaxyl-M, oxadixyl, furalaxyl, ofuras, benalaxyl, and nalaxyl.

(9) Carboxylic acid amide-based fungicides dimethomorph, flumorph, iprovalicalb, benthiavalcarb-isopropyl, mandipropamid, valina f and so on.

(10) SBI agents triflumizole, prochloraz, oxpoconazole fumarate, triadimefone, bittertanol, microbutanol, microbutanol , Hexaconazole, tebuconazole, propiconazole, prothioconazole, difenoconazole, iconconole and ibconazole. conazole, cyproconazole, tetraconazole, simconazole, metconazole, flusilazole, flusilazole, fluilazole, flusilazole, fluilazole, flusilazole, fluilazole (Trifoline), triadimenol, flutriafol, pyrifenox, tridemorph, dodemorph, fenpropimorphine, fenpropimorphin npropidin, spiroxamine, pyrisoxazole, fenhexamid, pyributicalcarb and the like.

(11) Strobilurin fungicides azoxystrobin, cresoxime-methyl, trifloxystrobin, methinostrobin, orysastrobrobin, orysastrobrobin Enestroburin, dimoxystrobin, picoxystrobin, pyribencarb, fluoxastrobin and the like.

(12) Anilinopyrimidine fungicide Cyprodinil, mepanipyrim, pyrimethanil and the like.

(13) Phenylpyrrole fungicides such as fludioxonil and fenpiclonil.

(14) Antibacterial fungicide kasugamycin, polyoxin, validamycin, streptomycin, oxytetracycline, blasticidin S (blasticidin-S).

(15) Other fungicides DKF-1001 (code number), MIF-1002 (code number), NF-171 (code number), S-2200 (code number), SB-4303 (code number), acibenzoral S methyl (Acibenzaolar-S-methyl), amisulbrom, amethoctrazine, isothianil, isofetamid, isoprothiolane, and iminotamine arbityl salt iminotadine triacetate), echromezol, ethaboxam ethaboxam), oxolinic acid, captaphor, carpropamide, quinoxyphen, chinoxythion, chloro, lotanyl, capro Diethofencaeb, diclocymet, diclomezine, dithianon, cyflufenamide, diflumetrim, simoxanyl il), sylthiofam, zoxamide, dazomet, thiadinyl, teclophthalam, tebufloquin, izo, trizol, z tolprocarb, tolmifanide, hydroxyisoxazole, pyriophenone, pyroquilon, fenoxanil, ferimon, ferimon amine), phthalide, bupirimate, famoxadone, fenamidone, fluazinam, fludiolide, fluoridoid, fluoridoid, fluorimide proquinazid, propamocarb hydrochloride, probenazole, pencyclon, holpet, metasulfocarb, metrafenone fenone), laminarin (laminarin), such as.

BAF-1120 (code number), MIF-1002 (code number), SYJ-264 (code number), NNF-0721 (code number), etc.

Insecticide:
(1) Organophosphorus insecticides acephate, azinephos-methyl, chlorfenvinphos, chlorpyrifos, chlorpyrifos-methyl, diaphos, diphos (Diazinon), diclofenthion, dichlorvos, dimethoate, dimethylvinphos, disulfoton, EPN, ethiphos, etiophos, ethophos os), fenitrothion, fenthion, isofenphos, isoxathion, malathion, methidathion, mevinphos, monotophos, monotophos -Methyl (oxydemethon-methyl), parathion (parathion), parathion-methyl (parathion-methyl), phentoate, folate, phosalone, phosmetone, phosphamidone n), phoxim, pirimiphos-methyl, profenofos, propaphos, prothiofos, pyrachlorfos, pyridafenthion Temefos, terbufos, tetrachlorvinphos, thiomethon, trichlorfon, bamidithione and the like.

(2) Carbamate insecticides aldicarb, alaniccarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfofan, carbosulfen (Fenobucarb), phenoxycarb (furoxycarb), furathiocarb, isoprocarb, metiocarb, methomyl, metolcarb, icylcarb, icylcarb arb), propoxur, thiodicarb, triazamate, XMC, xylylcarb and the like.

(3) Pyrethroid insecticides acrinathrin, allethrin, bifenthrin, cycloprothrin, cyfluthrin, beta-cythalthrin, beta-cyfluthrinth Cyhalothrin (lambda-cyhalothrin), gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin (theta-methrin) Sfenvalerate, etofenprox, fenpropatrin, fenvalerate, flucitrate, fluvalinate, tau-fluvalinate, tau-fluinate Halfenprox, methfluthrin, permethrin, phenothrin [(1R) -trans-isomer], pyrethrin, resmethrin, resmethrin, resmethrin Emissions (tefluthrin), tetramethrin (tetramethrin), such as tralomethrin (tralomethrin).

(4) Nereistoxin insecticides such as bensultap, cartap hydrochloride, thiocyclam and the like.

(5) Neonicotinoid insecticides acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiacloprid.

(6) Diamide-based insecticides such as chlorantraniliprole, cyantraniliprole, and flubendamide.

Cyclaniliprol, etc.

(7) Phenylpyrazole insecticides such as acetoprole, etiprole, fipronil, fluffiprole, pyrafluprole, pyriprole.

(8) Macrolide insecticides: abamectin, avermectin, avermectin benzoate, lepimectin, milbemectin, spinetoram, spinosadrum, spinosaramsp

(9) Benzoylurea insecticides bistrifluron, chlorfluazuron, diflubenzuron, fluazuron, flucyclohexuron, flufenhexuron, flufenoxuron Hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron and the like.

(10) Diacylhydrazine insecticides such as chromafenozide, halofenozide, methoxyphenozide, tebufenozide and the like.

(11) Other active insecticide ingredients Diafenthiuron, dicofol, dienochlor, endosulfan, flomequin, flonicamid, flufenerim di, flupyradion f , Hydramethylnon, hydroprene, indoxacarb, metaflumizone, metaaldehyde, methoprene, methoxychlor, and methoxychlor , Pyrifluquinazone, pyriproxyfen, rotenone, spirotetramat, sulfoxafluor, tolfenpyrad, tolfenpyrad Saw soil, fatty acid glycerides, starch (starch), rapeseed, adhesive (Polybutene), propylene glycol mono fatty acid esters, machine oil (petroleum oil), nicotine sulfate (nicotine-sulfate), phosphoric acid or the like ferric.

Triflumezopyrim, AKD-1193 (code number), MIE-1209 (code number), NA-89 (code number), NC-515 (code number), ME5382 (code number), ZDI-2501 (code) Number) etc.

(12) Acaricides acequinocyl, amidoflumet, amitraz, bifenazate, bromopropylate, clofentezine (clofente), clofentezine Cyhexatin, etoxazole, fenazaquin, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrylim , Hexythiazox, propargite, piflubumide, pyrimidifene, pyridaben, spirodicifene, spiromethifen, spiromethifen .

(13) Nematicide aldoxycarb, cadusafos, carbam sodium, 1,3-dichloropropene, DCIP, flusulfone, Fosthiazate, imicyafos, levamisole hydrochloride, mesulfenfos, methyl isothiocyanate, nectane mortantel

(14) Others Nuclear polyhedrosis virus (NPV), granule disease virus (GV), cytoplasmic polyhedrovirus virus (CPV), insect pox virus (EPV), etc. , Spore derived from Bacillus thuringiensis and produced crystal toxins, and mixtures thereof, microorganisms used as insecticides and nematicides such as Steinerne carpocapsae and Pasteuria penetrans Pesticides, insect pheromone agents, insect attractants, etc.

Hereinafter, the present invention will be described more specifically with reference to synthesis examples, formulation examples, and test examples of substituted phenyl ether compounds, but the present invention is not limited thereto.

[Synthesis Example 1]
Synthesis of 1,2,3-trifluoro-5-[[2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] methyl] benzene (1-140) A solution of -4-methyl-5- (2,2,2-trifluoroethylthio) phenol (500 mg, 2.08 mmol) in N, N-dimethylformamide (5 ml) and potassium carbonate (345 mg, 2.50 mmol) and 3 , 4,5-trifluorobenzyl bromide (Tokyo Chemical Industry Co., Ltd.) (515 mg, 2.29 mmol) was added at room temperature, and the mixture was 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 as a yellow oil (yield 624 mg, yield 78%).

[Synthesis Example 2]
Synthesis of 1-fluoro-5-methyl-4- (2,2,2-trifluoroethylsulfinyl) -2-[(3,4,5-trifluorophenyl) methoxy] benzene (1-141) , 3-trifluoro-5-[[2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] methyl] benzene (210 mg, 0.546 mmol) in dichloromethane (2 ml) 70% 3-chloroperbenzoic acid (150 mg, 0.608 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: ethyl acetate / n-hexane = 1/3) to give the title compound as white crystals (yield 170 mg, 78%).

[Synthesis Example 3]
Synthesis of 1- (cyclopropylmethylthio) -4-fluoro-2-methyl-5-[(3,4,5-trifluorophenyl) methoxy] benzene (1-684) 2-fluoro-4-methyl-5- By performing the same reaction and treatment as in Synthesis Example 1 using 5- (cyclopropylmethylthio) -2-fluoro-4-methyl-phenol instead of (2,2,2-trifluoroethylthio) phenol, The title compound (yield 100%) was obtained as white crystals.

[Synthesis Example 4]
Synthesis of 1- (cyclopropylmethylsulfinyl) -4-fluoro-2-methyl-5-[(3,4,5-trifluorophenyl) methoxy] benzene (1-685) 1,2,3-trifluoro- 5-[[2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] methyl] benzene instead of 1- (cyclopropylmethylthio) -4-fluoro-2-methyl- The same reaction and treatment as in Synthesis Example 2 were carried out using 5-[(3,4,5-trifluorophenyl) methoxy] benzene to give the title compound (yield 77%) as white crystals.

[Synthesis Example 5]
Synthesis of 1,2,3-trifluoro-5- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] benzene (2-7) 2 2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenol (545 mg, 2.27 mmol) in tetrahydrofuran (5 ml) with 2- (3,4,5-trifluorophenyl) ethanol (400 mg, 2.27 mmol), triphenylphosphine (714 mg, 2.72 mmol), diethyl azodicarboxylate (2.2 M toluene solution, 1.24 ml, 2.73 mmol) were added at 0 ° C., and the mixture was stirred at room temperature for 2 hours. did. 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 = 1/9) to give the title compound as a colorless oil (yield 650 mg, yield 72%).

[Synthesis Example 6]
Synthesis of 1,2,3-trifluoro-5- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenoxy] ethyl] benzene (2-8) 1 , 2,3-trifluoro-5-[[2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] methyl] benzene instead of 1,2,3-trifluoro By performing the same reaction and treatment as in Synthesis Example 2 using -5- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] benzene The title compound (yield 98%) was obtained as white crystals.

[Synthesis Example 7]
1,2,3-trifluoro-5- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] -1,1-dimethyl-ethyl] benzene ( 2-265) Synthesis of 2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenol (410 mg, 1.71 mmol) in a toluene solution (3 ml) with 2-methyl-2- ( 3,4,5-trifluorophenyl) propan-1-ol (350 mg, 1.71 mmol), phenoxydiphenylphosphine (manufactured by Tokyo Chemical Industry Co., Ltd.) (570 mg, 2.05 mmol), diethyl azodicarboxylate (2.2 M Toluene solution, 0.930 ml, 2.05 mmol) was added at 0 ° C. and stirred at room temperature for 2 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 111 mg, 15%) as a colorless oil.

[Synthesis Example 8]
1,2,3-trifluoro-5- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenoxy] -1,1-dimethyl-ethyl] benzene ( 2-266) Synthesis 1 instead of 1,2,3-trifluoro-5-[[2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] methyl] benzene , 2,3-trifluoro-5- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] -1,1-dimethyl-ethyl] benzene By conducting the same reaction and treatment as in Synthesis Example 2, the title compound (yield 21%) as a colorless oil was obtained.

[Synthesis Example 9]
Synthesis of 1,2,3-trifluoro-5- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethoxy] benzene (6-9) 2 -Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenol (240 mg, 0.999 mmol) in N, N-dimethylformamide solution (3 ml) and potassium carbonate (180 mg, 1.30 mmol) And 5- (2-bromoethoxy) -1,2,3-trifluorobenzene (268 mg, 1.05 mmol) were added at room temperature and stirred at the same temperature for 7 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 = 1/4) to give the title compound (yield 410 mg, yield 99%) as a white oil.

[Synthesis Example 10]
Synthesis of 1,2,3-trifluoro-5- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenoxy] ethoxy] benzene (6-10) 1 , 2,3-trifluoro-5-[[2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] methyl] benzene instead of 1,2,3-trifluoro By performing the same reaction and treatment as in Synthesis Example 2 using -5- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethoxy] benzene The title compound (yield 68%) was obtained as white crystals.

[Synthesis Example 11]
Synthesis of 1,2,3-trifluoro-5- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] propoxy] benzene (7-9) 2 -Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenol (300 mg, 1.25 mmol) in N, N-dimethylformamide solution (3 ml) and potassium carbonate (224 mg, 1.62 mmol) And 5- (3-bromopropoxy) -1,2,3-trifluorobenzene (403 mg, 1.50 mmol) were added at room temperature and stirred at the same temperature for 7 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 = 1/4) to give the title compound as a white oil (yield 440 mg, yield 82%).

[Synthesis Example 12]
Synthesis of 1,2,3-trifluoro-5- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenoxy] propoxy] benzene (7-10) 1 , 2,3-trifluoro-5-[[2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] methyl] benzene instead of 1,2,3-trifluoro By performing the same reaction and treatment as in Synthesis Example 2 using -5- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] propoxy] benzene The title compound (yield 80%) was obtained as white crystals.

[Synthesis Example 13]
Synthesis of 5- (cyclopropylmethylthio) -2-fluoro-4-methylphenol (9-3) 2-fluoro-4-methyl-5-sulfanylphenol (0.59 g, 3.73 mmol) in N, N-dimethyl To formamide solution (10 ml) was added potassium carbonate (0.77 g, 5.58 mmol), Rongalite (0.13 g, 1.10 mmol), and cyclopropylmethyl bromide (0.60 g, 4.44 mmol) at 0 ° C., Stir at room temperature for 4 hours. A 1N aqueous hydrochloric acid solution was poured into the reaction mixture, 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 = 1/10) to give the title compound (0.50 g, 64% yield) as a yellow oil.

[Synthesis Example 14]
1- [2,2-difluoro-2- (3,4,5-trifluorophenyl) ethoxy] -2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) benzene (2 -209) Synthesis of 2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenol (500 mg, 2.08 mmol) in N, N-dimethylformamide solution (5 ml) with potassium carbonate ( 374 mg, 2.71 mmol) and [2,2-difluoro-2- (3,4,5-trifluorophenyl) ethyl] trifluoromethanesulfonate (859 mg, 2.50 mmol) were added at 0 ° C. and 2 hours at room temperature. Stir. 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 a colorless oil (yield 723 mg, yield 80%).

[Synthesis Example 15]
1- [2,2-difluoro-2- (3,4,5-trifluorophenyl) ethoxy] -2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) benzene (2 -210) Synthesis 1- [2,2-Difluoro-2- (3,4,5-trifluorophenyl) ethoxy] -2-fluoro-4-methyl-5- (2,2,2-trifluoroethyl) To a chloroform solution (4 ml) of thio) benzene (370 mg, 0.897 mmol), 70% 3-chloroperbenzoic acid (200 mg, 0.897 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: ethyl acetate / n-hexane = 1/3) to give the title compound as white crystals (yield 370 mg, yield 97%).

[Synthesis Example 16]
1-chloro-2- [2,2-difluoro-2- (3,4,5-trifluorophenyl) ethoxy] -5-methyl-4- (2,2,2-trifluoroethylthio) benzene (2 -447) Synthesis of 2-chloro-4-methyl-5- (2,2,2-trifluoroethylthio) phenol (2.00 g, 7.79 mmol) in N, N-dimethylformamide solution (20 ml) Add potassium (1.40 g, 10.1 mmol) and [2,2-difluoro-2- (3,4,5-trifluorophenyl) ethyl] trifluoromethanesulfonate (3.20 g, 9.30 mmol) at 0 ° C. And stirred at room 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 = 1/5) to give the title compound as a colorless oil (yield 3.08 g, yield 88%).

[Synthesis Example 17]
1-chloro-2- [2,2-difluoro-2- (3,4,5-trifluorophenyl) ethoxy] -5-methyl-4- (2,2,2-trifluoroethylsulfinyl) benzene (2 -448) Synthesis of 1-chloro-2- [2,2-difluoro-2- (3,4,5-trifluorophenyl) ethoxy] -5-methyl-4- (2,2,2-trifluoroethyl) To a dichloromethane solution (4 ml) of thio) benzene (130 mg, 0.897 mmol), 70% 3-chloroperbenzoic acid (200 mg, 0.897 mmol) was added at 5 ° C. and stirred at room temperature for 3 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 (elution solvent: ethyl acetate / toluene = 1/30) to obtain the title compound as white crystals (yield 130 mg, yield 100%).

[Synthesis Example 18]
2,2-difluoro-5- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] -1,3-benzodioxole (2- 3) Synthesis of 2- (2,2- 2-methyl-4-methyl-5- (2,2,2-trifluoroethylthio) phenol (300 mg, 1.25 mmol) in tetrahydrofuran (2.5 ml) Difluoro-1,3-benzodioxo-5-yl) ethanol (252 mg, 1.25 mmol), triphenylphosphine (360 mg, 1.37 mmol), diethyl azodicarboxylate (2.2 M toluene solution, 0.590 ml, 1.50 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 = 1/9) to give the title compound as a colorless oil (yield 430 mg, 81%).

[Synthesis Example 19]
2,2-difluoro-5- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenoxy] ethyl] -1,3-benzodioxole (2- 4) Synthesis 1,2,3-trifluoro-5-[[2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] methyl] benzene instead of 2,2 Synthesis Example 2 Using -Difluoro-5- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] -1,3-benzodioxole The title compound (yield 87%) as white crystals was obtained by carrying out the same reaction and treatment as described above.

[Synthesis Example 20]
Synthesis of 1-fluoro-5-methyl-2- [2- (4-phenoxyphenyl) ethoxy] -4- (2,2,2-trifluoroethylthio) benzene (2-747) 2-fluoro-4- To a tetrahydrofuran solution (5 ml) of methyl-5- (2,2,2-trifluoroethylthio) phenol (300 mg, 1.25 mmol), 2- (4-phenoxyphenyl) ethanol (manufactured by Sigma-Aldrich) (321 mg, 1 .50 mmol), triphenylphosphine (652 mg, 1.50 mmol), diethyl azodicarboxylate (2.2 M toluene solution, 0.329 ml, 1.50 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 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 460 mg, 84%) as a yellow oil.

[Synthesis Example 21]
Synthesis of 1-fluoro-5-methyl-2- [2- (4-phenoxyphenyl) ethoxy] -4- (2,2,2-trifluoroethylsulfinyl) benzene (2-748) 1,2,3- Instead of trifluoro-5-[[2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] methyl] benzene, 1-fluoro-5-methyl-2- [2- (4-Phenoxyphenyl) ethoxy] -4- (2,2,2-trifluoroethylthio) benzene was used in the same reaction and treatment as in Synthesis Example 2 to give the title compound as a white crystal (yield 74 %).

[Synthesis Example 22]
Synthesis of N- [4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] phenyl] acetamide (11-6) 4- [2- Triethylamine (127 mg, 0.918 mmol) in [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] aniline (300 mg, 0.835 mmol) in dichloromethane (5 ml) And acetyl chloride (72.1 mg, 0.918 mmol) were added at 0 ° C. and stirred at room temperature for 1 hour. A dilute aqueous hydrochloric acid solution was poured into the reaction mixture, and the mixture was 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 as white crystals (yield 273 mg, 81%).

[Synthesis Example 23]
tert-Butyl N- [4- [2- [2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] phenyl] carbamate (11-63) and tert-butyl N-tert-butoxycarbonyl-N- [4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] phenyl] carbamate (11-65) Synthesis of 4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] aniline (1.00 g, 2.78 mmol) in acetonitrile (10 ml) Triethylamine (845 mg, 8.35 mmol), 4-dimethylaminopyridine (34.0 mg, 0.278 mmol) and di-dicarbonate ert- butyl (1.09 g, 5.01 mmol) was added at 0 ° C., and stirred at room temperature for 15 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 tert-butyl N- [4- [2- [2-fluoro-4-methyl- 5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] phenyl] carbamate (yield 642 mg, 50% yield) and tert-butyl N-tert-butoxycarbonyl-N- [4- [2- [ 2-Fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] phenyl] carbamate (yield 100 mg, yield 6%) was obtained.

[Synthesis Example 24]
tert-butyl N-tert-butoxycarbonyl-N- [2,6-difluoro-4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl Synthesis of phenyl] carbamate (11-71) To a tetrahydrofuran solution (5 ml) of 2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenol (400 mg, 1.67 mmol) was tert- Butyl N-tert-butoxycarbonyl-N- [2,6-difluoro-4- (2-hydroxyethyl) phenyl] carbamate (684 mg, 1.83 mmol), triphenylphosphine (524 mg, 2.00 mmol), azodicarboxylic acid Diethyl (2.2 M in toluene, 0.91 ml, 2.00 mmol) The mixture was added at ° 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 = 1/5) to give the title compound (yield 690 mg, yield 70%) as a yellow oil.

[Synthesis Example 25]
tert-Butyl N- [2,6-difluoro-4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] phenyl] carbamate (11- 69) Synthesis of tert-butyl N-tert-butoxycarbonyl-N- [2,6-difluoro-4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) Bismuth (III) bromide (41.4 mg, 92.3 μmol) was added to an acetonitrile solution (5 ml) of) phenoxy] ethyl] phenyl] carbamate (550 mg, 0.923 mmol) and stirred at 50 ° C. for 2 hours. Further, bismuth (III) bromide (41.4 mg, 92.3 μmol) was added, and the mixture was stirred at 50 ° C. 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: toluene) to give the title compound as a colorless oil (yield 227 mg, yield 50%).

[Synthesis Example 26]
tert-Butyl N- [2,6-difluoro-4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenoxy] ethyl] phenyl] carbamate (11- 70) Synthesis of tert-butyl N- [2,6-difluoro-4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] phenyl] To a dichloromethane solution (3 ml) of carbamate (120 mg, 0.242 mmol), 70% 3-chloroperbenzoic acid (53.7 mg, 0.218 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: ethyl acetate / n-hexane = 1/3) to give the title compound (yield 110 mg, 89%) as a colorless oil.

[Synthesis Example 27]
tert-butyl N-tert-butoxycarbonyl-N- [2,6-difluoro-4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] methyl Synthesis of phenyl] carbamate (10-25) tert-butyl N-tert-butoxycarbonyl-N- [2,6-difluoro-4- (2-hydroxyethyl) phenyl] carbamate instead of tert-butyl N-tert The title compound (yield 74) was obtained by carrying out the same reaction and treatment as in Synthesis Example 24 using -butoxycarbonyl-N- [2,6-difluoro-4- (2-hydroxymethyl) phenyl] carbamate. %).

[Synthesis Example 28]
tert-Butyl N- [2,6-difluoro-4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] methyl] phenyl] carbamate (10- 23) Synthesis of tert-butyl N-tert-butoxycarbonyl-N- [2,6-difluoro-4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) ) Tert-butyl N-tert-butoxycarbonyl-N- [2,6-difluoro-4- [2- [2-fluoro-4-methyl-5- (2,2) instead of phenoxy] ethyl] phenyl] carbamate , 2-trifluoroethylthio) phenoxy] methyl] phenyl] carbamate was used to carry out the same reaction and treatment as in Synthesis Example 25 to give a yellow oil. Compound (yield 59%) was obtained.

[Synthesis Example 29]
tert-butyl N- [2,6-difluoro-4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenoxy] methyl] phenyl] carbamate (10- 24) Synthesis of tert-butyl N- [2,6-difluoro-4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] phenyl] Tert-butyl N- [2,6-difluoro-4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] methyl] phenyl] instead of carbamate The same reaction and treatment as in Synthesis Example 26 were carried out using carbamate to obtain the title compound (97% yield) as white crystals.

[Synthesis Example 30]
tert-Butyl N- [4- [2- [2-Chloro-4-methyl-5- (cyclopropylmethylthio) phenoxy] ethyl] phenyl] carbamate (11-442) and tert-butyl N-tert-butoxycarbonyl- Synthesis of N- [4- [2- [2-chloro-4-methyl-5- (cyclopropylmethylthio) phenoxy] ethyl] phenyl] carbamate (11-444) 4- [2- [2-fluoro-4- 4- [2- [2-chloro-5- (cyclopropylmethylthio) 4-methylphenoxy] ethyl] aniline instead of methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] aniline By using the same reaction and treatment as in Synthesis Example 23, yellow oily tert-butyl N- [4- [2- [2-chloro Rho-4-methyl-5- (cyclopropylmethylthio) phenoxy] ethyl] phenyl] carbamate (52% yield) and tert-butyl N-tert-butoxycarbonyl-N- [4- [2- [2 -Chloro-4-methyl-5- (cyclopropylmethylthio) phenoxy] ethyl] phenyl] carbamate (yield 5%) was obtained.

[Synthesis Example 31]
tert-Butyl N-tert-Butoxycarbonyl-N- [4- [2- [2-Chloro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] -1,1-difluoroethyl ] Synthesis of 2,6-difluorophenyl] carbamate (11-305) N of 2-chloro-4-methyl-5- (2,2,2-trifluoroethylthio) phenol (3.70 g, 15.0 mmol) , N-dimethylformamide solution (50 ml) and potassium carbonate (2.40 g, 18.0 mmol) and [2- [4- [bis (tert-butoxycarbonyl) amino] 3,5-difluorophenyl] -2,2- Difluoroethyl] trifluoromethanesulfonate (7.90 g, 15.0 mmol) was added at 0 ° C. and stirred at room 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 = 1/5) to give the title compound as white crystals (yield 8.80 g, yield 93%).

[Synthesis Example 32]
tert-Butyl N- [4- [2- [2-Chloro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] -1,1-difluoroethyl] 2,6-difluorophenyl Synthesis of carbamate (11-302) tert-butyl N-tert-butoxycarbonyl-N- [2,6-difluoro-4- [2- [2-fluoro-4-methyl-5- (2,2,2) Tert-butyl N-tert-butoxycarbonyl-N- [4- [2- [2-chloro-4-methyl-5- (2,2,2) instead of -trifluoroethylthio) phenoxy] ethyl] phenyl] carbamate 2-trifluoroethylthio) phenoxy] -1,1-difluoroethyl] 2,6-difluorophenyl] carbamate using the same reaction and treatment as in Synthesis Example 25 To give the title compound (44% yield) as white crystals.

[Synthesis Example 33]
tert-Butyl N- [4- [2- [2-Chloro-4-methyl-5- (2,2,2-trifluoroethylsulfinyl) phenoxy] -1,1-difluoroethyl] 2,6-difluorophenyl Synthesis of carbamate (11-303) tert-butyl N- [2,6-difluoro-4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy ] Ethyl] phenyl] carbamate instead of tert-butyl N- [4- [2- [2-chloro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] -1,1- The same reaction and treatment as in Synthesis Example 26 were carried out using [difluoroethyl] 2,6-difluorophenyl] carbamate to obtain the title compound as a white crystal (yield 81%).

[Synthesis Example 34]
tert-Butyl N- [4- [2- [2-Chloro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] -1,1-difluoroethyl] 2,6-difluorophenyl ] Synthesis of —N-methyl-carbamate (11-307) tert-butyl N- [4- [2- [2-chloro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] 1,1-difluoroethyl] 2,6-difluorophenyl] carbamate (200 mg, 0.365 mmol) in tetrahydrofuran (3 ml) was added 60% sodium hydride (16.1 mg, 0.402 mmol) at room temperature. Stir for 5 minutes. Further methyl iodide (155 mg, 1.09 mmol) was added and stirred at room temperature for 15 hours. The reaction mixture was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/5) to give the title compound (yield 90.0 mg, yield 44%) as a colorless oil.

[Synthesis Example 35]

Synthesis of [2- [4- [bis (tert-butoxycarbonyl) amino] 3,5-difluorophenyl] -2,2-difluoroethyl] trifluoromethanesulfonate (12-91) tert-butyl N-tert-butoxycarbonyl -N- [4- (1,1-difluoro-2-hydroxyethyl) -2,6-difluorophenyl] carbamate (2.30 g, 5.60 mmol) and triethylamine (680 mg, 6.70 mmol) in dichloromethane (40 ml) ) Was added trifluoromethanesulfonic anhydride (1.70 g, 6.20 mmol) at 0 ° C., and the mixture was stirred at the same temperature for 1 hour. 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 to give the title compound (yield 2.60 g, 85%) as a brown oil.

[Synthesis Example 36]

Synthesis of tert-butyl N-tert-butoxycarbonyl-N- [4- (1,1-difluoro-2-hydroxyethyl) -2,6-difluorophenyl] carbamate (12-41) Ethyl 2- [4- [ Sodium borohydride (618 mg, 16.3 mmol) was added to a solution of bis (tert-butoxycarbonyl) amino] -3,5-difluorophenyl] -2,2-difluoroacetate (12.3 g, 27.2 mmol) in tetrahydrofuran (60 ml). ) At 0 ° C. and stirred at room temperature for 2 hours. The reaction mixture was poured into dilute aqueous hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound as white crystals (yield 7.90 g, 71%).

[Synthesis Example 37]
Synthesis of ethyl 2- [4- [bis (tert-butoxycarbonyl) amino] -3,5-difluorophenyl] -2,2-difluoroacetate (12-12) Ethyl 2- (4-amino-3,5- Triethylamine (12.1 g, 11.9 mmol), 4-dimethylaminopyridine (48.6 mg, 0.398 mmol) in an acetonitrile solution (20 ml) of difluorophenyl) -2,2-difluoroacetate (1.00 g, 3.98 mmol) ) And di-tert-butyl dicarbonate (1.91 g, 8.76 mmol) were added at 0 ° C. and stirred at room temperature for 15 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 1.06 g, yield 59%) as a red oil.

[Synthesis Example 38]
Synthesis of ethyl 2- (4-amino-3,5-difluorophenyl) -2,2-difluoroacetate (12-2) 2,6-difluoroaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) (15.0 g, 116 mmol) Hydrogen peroxide solution (25 ml) was slowly added to a DMSO solution (500 ml) of ethyl bromodifluoroacetate (Tokyo Chemical Industry Co., Ltd.) (70.7 g, 349 mmol) and ferrocene (2.16 g, 11.6 mmol) 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 as a brown oil (yield 25.7 g, yield 88%).

Table 13 shows ¹ HNMR spectrum (CDCl ₃ ) σ (ppm) value, melting point (° C.) and the like of the synthesis example and the compound according to the present invention produced according to the synthesis example. ¹ HNMR data was measured with a JNM-ECS400 spectrometer (manufactured by JEOL Ltd.).

Table 14 shows the ¹ HNMR spectrum (CDCl ₃ ) σ (ppm) value, melting point (° C.) and the like of the synthesis example and the compound according to the present invention produced according to the synthesis example. ¹ HNMR spectrum was measured with a JNM-ECS400 spectrometer (manufactured by JEOL Ltd.).

Hereinafter, Reference Synthesis Example 1 to Reference Synthesis Example 21 show synthesis examples in which the starting materials of Synthesis Examples 1 to 38 are synthesized from commercially available products, but are not limited thereto.

[Reference Synthesis Example 1]
Synthesis of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl) thio] phenol 2-Fluoro-4-methyl-5-sulfanylphenol (3.00 g, 19.0 mmol) N , N-dimethylformamide solution (30 ml), potassium carbonate (2.88 g, 20.8 mmol), Rongalite (0.900 g, 7.62 mmol), and 2,2,2-trifluoro-1-iodoethane (4.18 g) 19.9 mmol) at 0 ° C. and stirred at room temperature for 4 hours. A 1N aqueous hydrochloric acid solution was poured into the reaction mixture, 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 = 1/3) to give the title compound (yield 3.96 g, yield 87%) as a yellow oil.
¹ HNMR spectrum (CDCl ₃ ) σ: 7.16 (1H, d, J = 8.7 Hz), 6.94 (1H, d, J = 11.0 Hz), 5.13 (1H, br.s), 3.31 (2H, q, J = 9.8 Hz), 2.37 (3H, s).

[Reference Synthesis Example 2]
Synthesis of 2-fluoro-4-methyl-5-sulfanylphenol 2-fluoro-4-methylphenol (24.96 g, 197.9 mmol) (Sigma Aldrich) and triethylamine (26.03 g, 257.3 mmol) in dichloromethane To the solution (500 ml) was added ethyl chloroformate (23.62 g, 217.7 mmol) at 0 ° C., and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was poured into 1N aqueous hydrochloric acid and extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a colorless oil (yield 39.22 g, yield 100%). The obtained oil was added to chlorosulfonic acid (117.00 g, 1000 mmol) at 0 ° C. and reacted at room temperature for 18 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 to give a brown oil (yield 46.49 g, yield 78%). Red phosphorus (16.99 g, 548.4 mmol) and iodine (1.99 g, 7.84 mmol) were added to an acetic acid solution (130 ml) of the obtained oily substance 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 to give a brown oil (yield 30.13 g, yield 71%). The obtained oil was added to 10% aqueous potassium hydroxide solution (4 l) and heated to reflux for 3 hours. Concentrated 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 to give the title compound as a brown oil (yield 16.46 g, yield 94%).
¹ HNMR spectrum (CDCl ₃ ) σ: 6.94 (1H, d, J = 8.7 Hz), 6.88 (1H, d, J = 11.4 Hz), 4.95 (1H, br.s), 3.20 (1H, br.s), 2.23 (3H, s).

[Reference Synthesis Example 3]
Synthesis of 2- (3,4,5-trifluorophenyl) ethanol To a tetrahydrofuran solution (10 ml) of 1,2,3-trifluoro-5-vinylbenzene (Apollo) (1.00 g, 6.32 mmol) Dimethyl sulfide borane (d = 0.800, 0.660 ml, 7.04 mmol) was added at 0 ° C. and reacted at room temperature for 12 hours. Water (3.0 ml), 2N aqueous sodium hydroxide solution (15 ml) and 30% aqueous hydrogen peroxide (1.4 ml) were added, and the mixture was stirred at the same temperature for 6 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 809 mg, 73%) as a colorless oil.
¹ HNMR spectrum (CDCl ₃ ) σ: 6.89-6.83 (2H, m), 3.86 (2H, q, J = 6.0 Hz), 2.80 (2H, t, J = 6.0 Hz) ), 1.41 (1H, br.s).

[Reference Synthesis Example 4]
Synthesis of 2-methyl-2- (3,4,5-trifluorophenyl) propan-1-ol 3,4,5-trifluorobenzyl bromide (Tokyo Chemical Industry Co., Ltd.) (5.00 g, 22.2 mmol ) In acetonitrile (40 ml) with water (10 ml), potassium cyanide (1.74 g, 26.7 mmol) and 18-crown-6-ether (Tokyo Chemical Industry Co., Ltd.) (0.590 g, 2.22 mmol) at room temperature. And stirred at 50 ° C. 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 a colorless oil (yield 3.74 g, yield 98%). Sodium hydride (60%, 2.19 g, 54.6 mmol) and methyl iodide (15.5 g, 110 mmol) were added to a dimethoxyethane solution (40 ml) of the obtained oil at 0 ° C., and the mixture was stirred at room temperature for 1 hour. Stir. 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 a white solid (yield 4.00 g, yield 92%). A 60% aqueous sulfuric acid solution (40 ml) was added to the solid acetic acid solution (20 ml) obtained, and the mixture was stirred at 120 ° C. for 2 hours. Sodium nitrite (6.90 g, 100 mmol) was added at room temperature, and the mixture was stirred at 90 ° C. for 2 hours. did. Ice water was poured into the reaction mixture, and the precipitated solid was washed with water and then dried under reduced pressure to obtain a white solid (yield 3.86 g, yield 87%). Oxalyl chloride (3.36 g, 26.5 mmol) and N, N-dimethylformamide (0.10 mmol) were added to a dichloromethane solution (40 ml) of the obtained solid, and the mixture was refluxed for 1 hour. The reaction solution was concentrated under reduced pressure to obtain a yellow solid (4.63 g). Lithium aluminum hydride (686 mg, 18.1 mmol) was added to the obtained solid tetrahydrofuran solution (40 ml) at 0 ° C., and the mixture was stirred at room temperature for 1 hr. Diethyl ether was poured into the reaction mixture, a small amount of water was added, and the mixture was stirred at room temperature for 1 hour. The precipitate was removed by suction filtration, 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 colorless oil (yield 3.13 g, yield 87%).
¹ HNMR spectrum (CDCl ₃ ) σ: 7.01-6.97 (2H, m), 3.57 (2H, s), 1.29 (6H, s).

[Reference Synthesis Example 5]
Synthesis of 5- (2-bromoethoxy) -1,2,3-trifluorobenzene A solution of 3,4,5-trifluorophenol (Tokyo Chemical Industry Co., Ltd.) (1.13 g, 7.63 mmol) in tetrahydrofuran ( 10-ml) 2-bromo-1-ethanol (1.43 g, 11.4 mmol), triphenylphosphine (2.20 g, 8.39 mmol) and diethyl azodicarboxylate (2.2 M in toluene solution, 3.82 ml, (8.41 mmol) was added at 0 ° C. and stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/10) to give the title compound as a colorless oil (yield 1.44 g, yield 74%). Got.
¹ HNMR spectrum (CDCl ₃ ) σ: 6.58-6.50 (2H, m), 4.22 (2H, t, J = 6.0 Hz), 3.61 (2H, t, J = 6.0 Hz) ).

[Reference Synthesis Example 6]
Synthesis of 5- (3-bromopropoxy) -1,2,3-trifluorobenzene A solution of 3,4,5-trifluorophenol (manufactured by Tokyo Chemical Industry Co., Ltd.) (1.13 g, 7.63 mmol) in tetrahydrofuran ( 10-ml) 3-bromo-1-propanol (1.73 ng, 11.5 mmol), triphenylphosphine (2.20 g, 8.39 mmol) and diethyl azodicarboxylate (2.2 M in toluene, 3.82 ml, (8.41 mmol) was added at 0 ° C. and stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/10) to give the title compound as a colorless oil (yield 1.39 g, yield 68%). Got.
¹ HNMR spectrum (CDCl ₃ ) σ: 6.56-6.48 (2H, m), 4.04 (2H, t, J = 6.0 Hz), 3.57 (2H, t, J = 6.0 Hz) ), 2.30 (2H, q, J = 6.0 Hz).

[Reference Synthesis Example 7]
Synthesis of 2,2-difluoro-2- (3,4,5-trifluorophenyl) ethanol Ethyl 2,2-difluoro-2- (3,4,5-trifluorophenyl) acetate (Journal of Fluorine Chemistry, 2004) Year, synthesized in accordance with the method described in P.509 etc.) (1.00 g, 3.93 mmol) in ethanol solution (8 ml) was added sodium borohydride (800 mg, 3.15 mmol) at 0 ° C Stir at temperature for 1 hour. Ice water was poured into the reaction mixture, and the mixture was extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (yield 800 mg, yield 96%) as a colorless oil.
¹ H NMR spectrum (CDCl ₃ ) σ: 7.23-7.15 (2H, m), 4.00-3.92 (2H, m).

[Reference Synthesis Example 8]
Synthesis of [2,2-difluoro-2- (3,4,5-trifluorophenyl) ethyl] trifluoromethanesulfonate 2,2-difluoro-2- (3,4,5-trifluorophenyl) ethanol (2. 30 g, 10.8 mmol) and triethylamine (1.30 g, 12.8 mmol) in dichloromethane (25 ml) were added trifluoromethanesulfonic anhydride (3.40 g, 12.1 mmol) at 0 ° C. Stir for 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 purified by silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/7) to give the title compound (yield 3.20 g, yield 86%) as a yellow oil.
¹ HNMR spectrum (CDCl ₃ ) σ: 7.23-7.16 (2H, m), 4.67 (2H, t, J = 11.2 Hz).

[Reference Synthesis Example 9]
Synthesis of 2- (2,2-difluoro-1,3-benzodioxo-5-yl) ethanol 2,2-difluoro-5-vinyl-1,3-benzodioxole (1.90 g, 10.3 mmol) Dimethyl sulfide borane (d = 0.800, 1.4 ml, 11.8 mmol) was added to a tetrahydrofuran solution (31 ml) at 0 ° C. and reacted at room temperature for 7 hours. Water (5.0 ml), 2N aqueous sodium hydroxide solution (24 ml) and 30% aqueous hydrogen peroxide (2.2 ml) were added, and the mixture was stirred at the same 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 = 1/2) to give the title compound (yield 1.15 g, yield 55%) as a colorless oil.
¹ HNMR spectrum (CDCl ₃ ) σ: 6.9-6.91 (3H, m), 3.87-3.82 (2H, m), 2.85 (2H, t, J = 6.4 Hz), 1.42 (1H, br.s).

[Reference Synthesis Example 10]
Synthesis of 2,2-difluoro-5-vinyl-1,3-benzodioxole Methyltriphenylphosphonium bromide (2.20 g, 8.10 mmol) in tetrahydrofuran (20 ml) in sodium hydride (190 mg, 8.10 mmol) ) Was added at 0 ° C. and reacted at room temperature for 30 minutes. 2,2-difluoro-1,3-benzodioxo-5-carbaldehyde (manufactured by Tokyo Chemical Industry Co., Ltd.) (1.00 g, 5.40 mmol) was added and stirred at the same 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 = 1/7) to give the title compound as a colorless oil (yield 580 mg, yield 59%).
¹ HNMR spectrum (CDCl ₃ ) σ: 7.15 (1H, d, J = 1.8 Hz), 7.06 (1H, dd, J = 8.2, 1.8 Hz), 6.99 (1H, d , J = 8.2 Hz), 6.66 (1H, dd, J = 17.4, 11.0 Hz), 5.66 (1H, dd, J = 17.4 Hz), 5.25 (1H, dd, J = 11.0 Hz).

[Reference Synthesis Example 11]
Synthesis of 2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl) thio] phenol 2-Fluoro-4-methyl-5-sulfanylphenol (3.00 g, 19.0 mmol) N , N-dimethylformamide solution (30 ml), potassium carbonate (2.88 g, 20.8 mmol), Rongalite (0.900 g, 7.62 mmol), and 2,2,2-trifluoro-1-iodoethane (4.18 g) 19.9 mmol) at 0 ° C. and stirred at room temperature for 4 hours. A 1N aqueous hydrochloric acid solution was poured into the reaction mixture, 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 = 1/3) to give the title compound (yield 3.96 g, yield 87%) as a yellow oil.
¹ HNMR spectrum (CDCl ₃ ) σ: 7.16 (1H, d, J = 8.7 Hz), 6.94 (1H, d, J = 11.0 Hz), 5.13 (1H, br.s), 3.31 (2H, q, J = 9.8 Hz), 2.37 (3H, s).

[Reference Synthesis Example 12]
Synthesis of 2-fluoro-4-methyl-5-sulfanylphenol 2-fluoro-4-methylphenol (24.96 g, 197.9 mmol) (Sigma Aldrich) and triethylamine (26.03 g, 257.3 mmol) in dichloromethane To the solution (500 ml) was added ethyl chloroformate (23.62 g, 217.7 mmol) at 0 ° C., and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was poured into 1N aqueous hydrochloric acid and extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a colorless oil (yield 39.22 g, yield 100%). The obtained oil was added to chlorosulfonic acid (117.00 g, 1000 mmol) at 0 ° C. and reacted at room temperature for 18 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 to give a brown oil (yield 46.49 g, yield 78%). Red phosphorus (16.99 g, 548.4 mmol) and iodine (1.99 g, 7.84 mmol) were added to an acetic acid solution (130 ml) of the obtained oily substance 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 to give a brown oil (yield 30.13 g, yield 71%). The obtained oil was added to 10% aqueous potassium hydroxide solution (4 l) and heated to reflux for 3 hours. Concentrated 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 to give the title compound as a brown oil (yield 16.46 g, yield 94%).
¹ HNMR spectrum (CDCl ₃ ) σ: 6.94 (1H, d, J = 8.7 Hz), 6.88 (1H, d, J = 11.4 Hz), 4.95 (1H, br.s), 3.20 (1H, br.s), 2.23 (3H, s).

[Reference Synthesis Example 13]
Synthesis of 4- [2- [2-fluoro-4-methyl-5- (2,2,2-trifluoroethylthio) phenoxy] ethyl] aniline 2-Fluoro-4-methyl-5- (2,2, 2- (4-aminophenyl) ethanol (Tokyo Chemical Industry Co., Ltd.) (4.20 g, 30.6 mmol) in a tetrahydrofuran solution (30 ml) of 2-trifluoroethylthio) phenol (6.70 g, 27.9 mmol) , Triphenylphosphine (8.80 g, 33.5 mmol) and diethyl azodicarboxylate (2.2 M toluene solution, 15 ml, 33.0 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 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 6.70 g, 67% yield) as a yellow oil.
¹ HNMR spectrum (CDCl ₃ ) σ: 7.10 (1H, d, J = 8.7 Hz), 7.07 (2H, d, J = 8.2 Hz), 6.95 (1H, d, J = 11) .9 Hz), 6.66 (2H, d, J = 8.7 Hz), 4.14 (2H, t, J = 7.3 Hz), 3.26 (2H, q, J = 9.6 Hz), 3 .00 (2H, t, J = 7.3 Hz), 2.39 (3H, s).

[Reference Synthesis Example 14]
Synthesis of tert-butyl N-tert-butoxycarbonyl-N- [2,6-difluoro-4- (2-hydroxyethyl) phenyl] carbamate tert-butyl N-tert-butoxycarbonyl-N- (2,6-difluoro Dimethyl sulfide borane (d = 0.850, 1.4 ml, 15.1 mmol) was added to a tetrahydrofuran solution (20 ml) of -4-vinylphenyl) carbamate (3.58 g, 10.1 mmol) at 0 ° C., and at room temperature. The reaction was performed for 12 hours. Water (6.0 ml), 2N aqueous sodium hydroxide solution (30 ml) and 30% aqueous hydrogen peroxide (3 ml) were added, and the mixture was stirred at the same temperature for 6 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 = 1/2) to give the title compound (yield 1.36 g, yield 36%) as red crystals.
¹ HNMR spectrum (CDCl ₃ ) σ: 6.83 (2H, d, J = 8.2 Hz), 3.86 (2H, t, J = 6.0 Hz), 2.86 (2H, t, J = 6) .0Hz), 1.43 (18H, s).

[Reference Synthesis Example 15]
Synthesis of tert-butyl N-tert-butoxycarbonyl-N- (2,6-difluoro-4-vinylphenyl) carbamate 60% in methyltriphenylphosphonium bromide (4.85 g, 17.5 mmol) in tetrahydrofuran (40 ml) Sodium hydride (700 mg, 17.5 mmol) was added at 0 ° C., and the mixture was stirred at the same temperature for 30 minutes. Further, tert-butyl N-tert-butoxycarbonyl-N- (2,6-difluoro-4-formylphenyl) carbamate (4.17 g, 11.7 mmol) was added at 0 ° C. and reacted 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 = 1/5) to give the title compound as a colorless oil (yield 3.58 g, yield 86%).
¹ HNMR spectrum (CDCl ₃ ) σ: 6.96 (2H, d, J = 8.2 Hz), 6.61 (1H, dd, J = 17.4, 11.0 Hz), 5.77 (1H, d , J = 17.4 Hz), 5.38 (1H, d, J = 11.0 Hz), 1.42 (18H, s).

[Reference Synthesis Example 16]
Synthesis of tert-butyl N-tert-butoxycarbonyl-N- [2,6-difluoro-4- (hydroxymethyl) phenyl] carbamate tert-butyl N-tert-butoxycarbonyl-N- (2,6-difluoro-4 -To formylphenyl) carbamate (962 mg, 2.69 mmol) in tetrahydrofuran (30 ml) was added sodium borohydride (81.5 mg, 2.15 mmol) at 0 ° C. and stirred at the same temperature for 1 hour. The reaction mixture was poured into dilute aqueous hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (yield 862 mg, 89%) as yellow crystals.
¹ HNMR spectrum (CDCl ₃ ) σ: 6.96 (2H, d, J = 8.2 Hz), 4.71 (2H, s), 1.42 (18H, s).

[Reference Synthesis Example 17]
Synthesis of tert-butyl N-tert-butoxycarbonyl-N- (2,6-difluoro-4-formylphenyl) carbamate 4-Amino-3,5-difluorobenzaldehyde (1.68 g, 10.7 mmol) in acetonitrile solution ( 20 ml), triethylamine (3.25 g, 32.1 mmol), 4-dimethylaminopyridine (131 mg, 1.07 mmol) and di-tert-butyl dicarbonate (5.13 g, 23.5 mmol) were added at 0 ° C. Stir at room temperature for 15 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 962 mg, 25% yield) as yellow crystals.
¹ HNMR spectrum (CDCl ₃ ) σ: 9.94 (1H, s), 7.48 (2H, d, J = 7.3 Hz), 1.43 (18H, s).

[Reference Synthesis Example 18]
Synthesis of 4-amino-3,5-difluorobenzaldehyde Copper (II) chloride (10. 0 g, 77.0 mmol) and concentrated hydrochloric acid (15 ml) were added and stirred at 90 ° C. for 10 hours. Saturated sodium hydrogen carbonate was poured into the reaction mixture, 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 = 1/5) to give the title compound as white crystals (yield 1.68 g, yield 28%).
¹ HNMR spectrum (CDCl ₃ ) σ: 9.73 (1H, s), 7.39 (2H, d, J = 8.4 Hz), 4.33 (2H, br.s).

[Reference Synthesis Example 19]
Synthesis of 4- [2- [2-chloro-5- (cyclopropylmethylthio) 4-methylphenoxy] ethyl] aniline 2-chloro-5- (cyclopropylmethylthio) -4-methylphenol (1.00 g, 4. 40 mmol) in tetrahydrofuran (10 ml), 2- (4-aminophenyl) ethanol (Tokyo Chemical Industry Co., Ltd.) (660 mg, 4.80 mmol), triphenylphosphine (1.40 g, 5.20 mmol), azodicarboxylic acid Diethyl (2.2M toluene solution, 2.36 ml, 5.20 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 = 1/3) to give the title compound as a yellow oil (yield 931 mg, 61%).
¹ HNMR spectrum (CDCl ₃ ) σ: 7.15 (1H, s), 7.10 (2H, d, J = 8.7 Hz), 6.84 (1H, s), 6.66 (2H, d, J = 8.2 Hz), 4.12 (2H, t, J = 7.3 Hz), 3.03 (2H, t, J = 7.3 Hz), 2.75 (2H, d, J = 6.9 Hz) ), 2.29 (3H, s), 1.02-0.97 (1H, m), 0.59-0.54 (2H, m), 0.25-0.21 (2H, m).

[Reference Synthesis Example 20]
Synthesis of 2-chloro-5- (cyclopropylmethylthio) -4-methylphenol Carbonate was added to a solution of 2-chloro-4-methyl-5-sulfanylphenol (24.8 g, 142 mmol) in N, N-dimethylformamide (140 ml). Potassium (23.6 g, 171 mmol), Rongalite (6.57 g, 42.6 mmol), and cyclopropylmethyl bromide (20.1 g, 149 mmol) were added at 0 ° C. and stirred at room temperature for 2 hours. A 1N aqueous hydrochloric acid solution was poured into the reaction mixture, 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 = 1/4) to give the title compound (21.5 g, 66% yield) as a brown oil.
¹ HNMR spectrum (CDCl ₃ ) σ: 7.26 (1H, s), 6.92 (1H, s), 5.42 (1H, s), 2.81 (2H, d, J = 7.2 Hz) , 2.26 (3H, s), 1.12-1.02 (1H, m), 0.63-0.58 (2H, m), 0.29-0.25 (2H, m).

[Reference Synthesis Example 21]
Synthesis of 2-chloro-4-methyl-5-sulfanylphenol Similar to Reference Example 12 using 2-chloro-4-methylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) instead of 2-fluoro-4-methylphenol By performing the reaction and treatment, the title compound (yield 100%) was obtained as white crystals.
¹ HNMR spectrum (CDCl ₃ ) σ: 7.09 (1H, s), 6.95 (1H, s), 5.33 (1H, br.s), 3.29 (1H, br.s), 2 .22 (3H, s).

Next, specific examples of methods for formulating the compounds of the present invention as agricultural and horticultural insecticides and acaricides are shown in Formulation Examples 1 to 5.
[Formulation Example 1] Powder A mixture of the compound of Synthesis Example 1 (2 parts by weight), isopropyl phosphate (1 part by weight) as a fluidity improver and clay (97 parts by weight) as a solid carrier was uniformly ground and mixed. Thus, a powder containing 2% by weight of the active ingredient can be obtained. Furthermore, each powder agent can be obtained by the same method except that the compounds shown in Tables 1 to 8 are used instead of the compound of Synthesis Example 1.

[Formulation Example 2] Wetting Agent Compound (20 parts by weight) of Synthesis Example 1, sodium alkylbenzene sulfonate (3 parts by weight) as an anionic surfactant, and polyoxyethylene alkylphenyl ether (non-ionic surfactant) A wettable powder containing 20% by weight of the active ingredient can be obtained by uniformly crushing and mixing a mixture of 5 parts by weight) and clay (72 parts by weight) as a solid carrier. Furthermore, a wettable powder can be obtained in the same manner except that each compound shown in Tables 1 to 8 is used instead of the compound of Synthesis Example 1.

[Formulation Example 3] Emulsion The compound of Synthesis Example 1 (30 parts by weight), methyl naphthalene (40 parts by weight) as a liquid carrier and polyoxyethylene alkylphenyl ether (30 parts by weight) as a nonionic surfactant are mixed and dissolved. By doing so, an emulsion containing 30% by weight of the active ingredient can be obtained. Furthermore, emulsions can be obtained in the same manner except that the compounds shown in Tables 1 to 8 are used in place of the compound of Synthesis Example 1.

[Formulation Example 4] Flowable Agent The compound of Synthesis Example 1 (25 parts by weight), polyoxyethylene alkyl ether (1 part by weight) as a nonionic surfactant, and sodium alkylnaphthalene sulfonate (1 as an anionic surfactant) Parts by weight), xanthan gum (1 part by weight) as a thickener, and water (72 parts by weight) as a liquid carrier are uniformly mixed to obtain a flowable agent containing 25% by weight of the active ingredient. Further, each flowable agent can be obtained by the same method except that the compounds shown in Tables 1 to 8 are used instead of the compound of Synthesis Example 1.

[Formulation Example 5] Granule The compound of Synthesis Example 1 (5 parts by weight), sodium lauryl sulfate (1 part by weight) as a surfactant, calcium lignin sulfonate (5 parts by weight) as a binder, bentonite (30 Parts by weight) and clay (59 parts by weight), water (15 parts by weight) is further added and kneaded by a kneader, granulated by a granulator, and further dried by a fluid dryer to obtain an active ingredient. Granules containing 5% by weight can be obtained. Further, each granule can be obtained by the same method except that each compound shown in Table 1 to Table 8 is used in place of the compound of Synthesis Example 1.

Specific examples of the evaluation of the control effect using the pest control agent according to the present invention obtained as described above are shown in Test Examples 1 to 7.
[Test Example 1] Control test against brown planthopper Rice 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 by the following formula (a). The test was carried out in two consecutive systems.

As representative examples, the compounds of compound numbers 1-1, 1-2, 1-3, 1-106, 1-140, 1-245, and 2-7 showed a death rate of 80% or more.

Moreover, the compound Nos. 1-1020, 2-3, 2-4, 2-727, 2-919, and 2-928 showed a death rate of 80% or more.

Further, the compound No. 11-284 showed a death rate of 80% or more.

[Test Example 2] 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-hour illumination), and the number of adults and larvae parasitized 4 days after the treatment was examined. The test was carried out in two consecutive systems.

As representative examples, the compounds Nos. 1-629, 1-760, 2-166, 2-209, and 6-9 showed a control value of 80% or more.

Further, the compounds Nos. 2-3, 2-728, 2-782, 2-794, 2-870, 2-919, 2-920, 2-995, and 2-1020 have a control value of 80% or more. It was.

The compounds Nos. 10-25, 10-62, 10-64, 11-69, 11-70, and 11-187 showed a control value of 80% or more.

Further, the compound numbers 11-123, 11-124, 11-128, 11-161, 11-344, 11-376, 11-452, 11-455, 11-465, 11-499, 11-502, 11 The compound of −511 showed a control value of 80% or more.

[Test Example 3] Control test against spider mite Ten adult female spider mites were released at a rate of 10 persimmon seedlings cultivated in plastic cups. One day after the release, the kidney seedlings 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 the treatment, it was placed in a constant temperature room at 25 ° C. (16 hours illumination), and the number of female adults parasitized 8 days after the treatment was examined. The test was carried out in two consecutive systems.

As representative examples, the compound numbers 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-17, 1-18, 1-47, 1-48, 1-53 1-54, 1-55, 1-56, 1-57, 1-58, 1-61, 1-62, 1-73, 1-74, 1-89, 1-90, 1-95, 1 -96, 1-97, 1-99, 1-100, 1-102, 1-103, 1-106, 1-107, 1-108, 1-109, 1-110, 1-111, 1-118 1-119, 1-132, 1-140, 1-141, 1-142, 1-147, 1-179, 1-187, 1-188, 1-199, 1-200, 1-209, 1 -210, 1-211, 1-212, 1-213, 1-214, 1-215, 1-216, 1-227, 1-228, 1-237, 1- 38, 1-243, 1-244, 1-245, 1-246, 1-275, 1-276, 1-288, 1-293, 1-294, 1-305, 1-306, 1-307, 1-308, 1-333, 1-334, 1-372, 1-389, 1-390, 1-403, 1-404, 1-409, 1-410, 1-421, 1-422, 1- 448, 1-471, 1-472, 1-495, 1-496, 1-508, 1-559, 1-560, 1-561, 1-568, 1-569, 1-597, 1-608, 1-609, 1-616, 1-617, 1-628, 1-629, 1-652, 1-653, 1-684, 1-685, 1-702, 1-703, 1-708, 1- 709, 1-714, 1-715, 1-720, 1-721, 1-722 1-723, 1-736, 1-737, 1-752, 1-753, 1-768, 1-769, 1-921, 1-952, 1-953, 1-954, 1-961, 1- 962, 1-963, 2-7, 2-8, 2-34, 2-35, 2-58, 2-59, 2-66, 2-67, 2-82, 2-83, 2-93, 2-108, 2-116, 2-117, 2-140, 2-141, 2-158, 2-160, 2-162, 2-164, 2-166, 2-167, 2-168, 2- 176, 2-184, 2-185, 2-186, 2-193, 2-194, 2-200, 2-201, 2-202, 2-203, 2-204, 2-205, 2-206, 2-207, 2-208, 2-209, 2-210, 2-211, 2-212, 2-239, 2-24 0, 2-249, 2-265, 2-266, 2-311, 312, 2-339, 2-340, 2-363, 2-364, 2-413, 2-414, 2-421, 2-423, 2-431, 2-432, 2-447, 2-448, 2-449, 2-450, 2-487, 2-488, 2-497, 2-498, 2-521, 2- 522, 2-557, 2-558, 2-591, 2-592, 2-611, 2-612, 2-625, 2-626, 2-639, 2-655, 2-656, 2-699, 2-700, 3-1, 3-2, 3-9, 3-10, 6-3, 6-4, 6-5, 6-6, 6-7, 6-8, 6-9, 6- 10, 6-39, 6-40, 6-75, 6-76, 6-83, 6-84, 7-9, 7-10 compounds have a control value of 80% or more It was.

Also, 1-193, 1-194, 1-964, 1-965, 1-1016, 1-1017, 1-1020, 1-1021, 1-1024, 1-1026, 1-1027, 2-3, 2-4, 2-401, 2-402, 2-405, 2-406, 2-417, 2-439, 2-440, 2-443, 2-444, 2-527, 2-528, 2- 725, 2-726, 2-727, 2-728, 2-729, 2-730, 2-731, 2-732, 2-733, 2-734, 2-735, 2-736, 2-737, 2-738, 2-739, 2-740, 2-743, 2-744, 2-745, 2-746, 2-747, 2-748, 2-749, 2-750, 2-757, 2- 758, 2-763, 2-764, 2-781, 2-782, 2- 83, 2-784, 2-791, 2-792, 2-793, 2-794, 2-801, 2-802, 2-803, 2-804, 2-813, 2-814, 2-815, 2-816, 2-817, 2-818, 2-823, 2-824, 2-825, 2-826, 2-835, 2-836, 2-837, 2-838, 2-839, 2- 840, 2-841, 2-842, 2-843, 2-844, 2-845, 2-846, 2-847, 2-848, 2-849, 2-850, 2-851, 2-852, 2-853, 2-855, 2-856, 2-858, 2-860, 2-861, 2-862, 2-863, 2-865, 2-866, 2-867, 2-868, 2- 869, 2-870, 2-871, 2-872, 2-873, 2-874 2-875, 2-876, 2-877, 2-878, 2-879, 2-880, 2-882, 2-885, 2-886, 2-887, 2-888, 2-889, 2- 890, 2-891, 2-892, 2-893, 2-894, 2-895, 2-896, 2-897, 2-898, 2-899, 2-900, 2-901, 2-902, 2-903, 2-904, 2-905, 2-906, 2-907, 2-908, 2-909, 2-910, 2-911, 2-912, 2-913, 2-914, 2- 915, 2-916, 2-917, 2-918, 2-919, 2-920, 2-921, 2-922, 2-923, 2-924, 2-925, 2-926, 2-927, 2-928, 2-929, 2-930, 2-931, 2-932, 2-9 33, 2-934, 2-935, 2-936, 2-937, 2-939, 2-939, 2-940, 2-941, 2-944, 2-945, 2-946, 2-947, 2-948, 2-949, 2-950, 2-951, 2-960, 2-961, 2-962, 2-963, 2-964, 2-965, 2-966, 2-967, 2- 968, 2-969, 2-970, 2-971, 2-974, 2-975, 2-976, 2-977, 2-978, 2-979, 2-986, 2-987, 2-987, 2-989, 2-994, 2-995, 2-996, 2-997, 2-1000, 2-1001, 2-1004, 2-1005, 2-1008, 2-1009, 2-1010, 2- 1011, 2-1020, 2-1021, 2-1022, 2 1023, 2-1024, 2-1025, 2-1026, 2-1027, 2-1030, 2-1031, 2-1032, 2-1033, 2-1034, 2-1035, 2-1040, 2-1041, 2-1042, 2-1043, 2-1046, 2-1047, 2-1048, 2-1049, 2-1050, 2-1051, 2-1052, 2-1053, 2-1068, 2-1069, 2- The compounds of 1070, 2-1072, 2-1073, 2-1074, 2-1076, 2-1077, 2-1078, 2-1080, 2-1081, and 2-1082 showed a control value of 80% or more.

Further, the compound numbers 10-23, 10-24, 10-25, 10-62, 10-64, 10-65, 10-66, 11-6, 11-15, 11-32, 11-41, 11 -64, 11-65, 11-69, 11-70, 11-71, 11-85, 11-98, 11-168, 11-174, 11-180, 11-187, 11-191, 11-217 11-228, 11-284, 11-286, 11-287, 11-289, 11-290, 11-291, 11-302, 11-303, 11-305, 11-307, 11-359, 11 The compounds -360, 11-362, 11-388, and 11-444 showed a control value of 80% or more.

In addition, the compound numbers 11-8, 11-11, 11-20, 11-37, 11-46, 11-49, 11-51, 11-52, 11-54, 11-55, 11-58, 11 -59, 11-62, 11-92, 11-123, 11-124, 11-126, 11-128, 11-131, 11-133, 11-137, 11-144, 11-146, 11-147 11-156, 11-158, 11-159, 11-161, 11-162, 11-164, 11-170, 11-176, 11-182, 11-185, 11-189, 11-199, 11 -214, 11-219, 11-221, 11-272, 11-275, 11-298, 11-337, 11-344, 11-346, 11-376, 11-383, 11-392, 1 -393, 11-448, 11-449, 11-450, 11-451, 11-452, 11-453, 11-454, 11-455, 11-464, 11-465, 11-468, 11-470 11-475, 11-477, 11-478, 11-479, 11-484, 11-485, 11-486, 11-491, 11-494, 11-495, 11-496, 11-497, 11 -498, 11-500, 11-502, 11-503, 11-506, 11-508, 11-509, 11-511, 11-512, 11-513, 11-515, 11-517, 11-518 11-519 and 11-520 showed a control value of 80% or more.

Among the above compounds, 1-147, 1-179, 1-214, 1-288, 1-403, 1-409, 1-708, 1-709, 1-921, 1-963, 2-82, 2 -93 indicates a control value of 80% or more and less than 90%, 1-56, 1-103, 1-216, 1-238, 1-438, 1-472, 1-508, 1-653, 1-721, 1-723, 1-737, 1-753, 1-768, 1-962, 2-363, 2-364, 2-432, 2-522, 2-700, 6-40 have a control value of 90% or more and 100 %, 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-17, 1-18, 1-47, 1-48, 1-53, 1 -54, 1-55, 1-57, 1-58, 1-61, 1-62, 1-73, 1-74, 1-89, 1-90, 1- 5, 1-96, 1-97, 1-99, 1-100, 1-102, 1-106, 1-107, 1-108, 1-109, 1-110, 1-111, 1-1811- 119, 1-132, 1-140, 1-141, 1-142, 1-187, 1-188, 1-199, 1-200, 1-209, 1-210, 1-211, 1-212, 1-213, 1-215, 1-227, 1-228, 1-237, 1-243, 1-244, 1-245, 1-246, 1-275, 1-276, 1-293, 1- 294, 1-305, 1-306, 1-307, 1-308, 1-333, 1-334, 1-372, 1-389, 1-390, 1-410, 1-421, 1-422, 1-448, 1-471, 1-495, 1-496, 1-559, 1-56 1-561, 1-568, 1-569, 1-597, 1-608, 1-609, 1-616, 1-617, 1-628, 1-629, 1-652, 1-684, 1 -685, 1-702, 1-703, 1-714, 1-715, 1-720, 1-722, 1-736, 1-752, 1-769, 1-952, 1-953, 1-954 1-961, 2-7, 2-8, 2-34, 2-35, 2-58, 2-59, 2-66, 2-67, 2-83, 2-108, 2-116, 2 -117, 2-140, 2-141, 2-158, 2-160, 2-162, 2-164, 2-166, 2-167, 2-168, 2-176, 2-184, 2-185 2-186, 2-193, 2-194, 2-200, 2-201, 2-202, 2-203, 2 -204, 2-205, 2-206, 2-207, 2-208, 2-209, 2-210, 2-211, 2-212, 2-239, 2-240, 2-249, 2-265 2-266, 2-311, 312, 2-339, 2-340, 2-413, 2-414, 2-421, 2-423, 2-431, 2-447, 2-448, 2 -449, 2-450, 2-487, 2-488, 2-497, 2-498, 2-521, 2-557, 2-558, 2-591, 2-592, 2-611, 2-612 2-625, 2-626, 2-639, 2-655, 2-656, 2-699, 3-1, 3-2, 3-9, 3-10, 6-3, 6-4, 6 -5, 6-6, 6-7, 6-8, 6-9, 6-10, 6-39, 6-75, 6-76, 6-83, -84,7-9,7-10 showed a 100% value control.

Among the above compounds, 2-939 has a control value of 80% or more and less than 90%, and 1-1027, 2-850, 2-868, 2-885, 2-887, 2-889, 2-908, 2-921, 2-9271-1027, indicating a control value of 90% or more and less than 100%, 1-193, 1-194, 1-964, 1-965, 1-1016, 1-1017, 1-1020, 1-1021, 1-1024, 1-1026, 2-3, 2-4, 2-401, 2-402, 2-405, 2-406, 2-417, 2-439, 2-440, 2- 443, 2-444, 2-527, 2-528, 2-725, 2-726, 2-727, 2-728, 2-729, 2-730, 2-731, 2-732, 2-733, 2-734, 2-735, 2-736, 2-737, -738, 2-739, 2-740, 2-743, 2-744, 2-745, 2-746, 2-747, 2-748, 2-749, 2-750, 2-757, 2-758 2-763, 2-764, 2-781, 2-782, 2-783, 2-784, 2-791, 2-792, 2-793, 2-794, 2-801, 2-802, 2 -803, 2-804, 2-813, 2-814, 2-815, 2-816, 2-817, 2-818, 2-823, 2-824, 2-825, 2-826, 2-835 2-836, 2-837, 2-838, 2-839, 2-840, 2-841, 2-842, 2-843, 2-844, 2-845, 2-846, 2-847, 2 -848, 2-849, 2-851, 2-852, 2-853, 2-8 5, 2-856, 2-858, 2-860, 2-861, 2-862, 2-863, 2-865, 2-866, 2-867, 2-869, 2-870, 2-871, 2-872, 2-873, 2-874, 2-875, 2-876, 2-877, 2-878, 2-879, 2-880, 2-882, 2-886, 2-888, 2- 890, 2-891, 2-892, 2-893, 2-894, 2-895, 2-896, 2-897, 2-898, 2-899, 2-900, 2-901, 2-902, 2-903, 2-904, 2-905, 2-906, 2-907, 2-909, 2-910, 2-911, 2-912, 2-913, 2-914, 2-915, 2- 916, 2-917, 2-918, 2-919, 2-920, 2-922, 2 -923, 2-924, 2-925, 2-926, 2-929, 2-929, 2-930, 2-931, 2-932, 2-933, 2-934, 2-935, 2-936 2-937, 2-938, 2-940, 2-941, 2-944, 2-945, 2-946, 2-947, 2-948, 2-949, 2-950, 2-951, -960, 2-961, 2-962, 2-963, 2-964, 2-965, 2-966, 2-967, 2-968, 2-969, 2-970, 2-971, 2-974 2-975, 2-976, 2-977, 2-978, 2-979, 2-986, 2-987, 2-988, 2-989, 2-994, 2-995, 2-996, 2 -997, 2-1000, 2-1001, 2-1004, 2-1005, -1008, 2-1009, 2-1010, 2-1011, 2-1020, 2-1021, 2-1022, 2-1023, 2-1024, 2-1025, 2-1026, 2-1027, 2-1030 2-1031, 2-1032, 2-1033, 2-1034, 2-1035, 2-1040, 2-1041, 2-1042, 2-1043, 2-1046, 2-1047, 2-1048, 2 -1049, 2-1050, 2-1051, 2-1052, 2-1053, 2-1068, 2-1069, 2-1070, 2-1072, 2-1073, 2-1074, 2-1076, 2-1077 , 2-1078, 2-1080, 2-1081, 2-1082, 3-53, and 3-54 showed a control value of 100%.

Of the above compounds, 11-362 exhibits a control value of 80% or more and less than 90%, and 11-64, 11-85, 11-174, 11-217, and 11-228 have a control value of 90% or more and less than 100%. 10-23, 10-24, 10-25, 10-62, 10-64, 10-65, 10-66, 11-6, 11-15, 11-32, 11-41, 11-65 11-69, 11-70, 11-71, 11-98, 11-168, 11-180, 11-187, 11-191, 11-284, 11-286, 11-287, 11-289, 11 -290, 11-291, 11-302, 11-303, 11-305, 11-307, 11-359, 11-360, 11-388, and 11-444 showed a control value of 100%.

Of the above compounds, 11-383, 11-455, 11-496, 11-497, and 11-518 have a control value of 80% or more and less than 90%, and 11-11, 11-20, 11-46, 11-137, 11-161, 11-170, 11-219, 11-452, 11-453, 11-494, 11-495, and 11-498 show control values of 90% or more and less than 100%, and 11-8 11-37, 11-49, 11-51, 11-52, 11-54, 11-55, 11-58, 11-59, 11-62, 11-92, 11-123, 11-124, 11 -126, 11-128, 11-131, 11-133, 11-144, 11-146, 11-147, 11-156, 11-158, 11-159, 11-162, 11-164, 11-176 , 1-182, 11-185, 11-189, 11-199, 11-214, 11-221, 11-272, 11-275, 11-298, 11-337, 11-344, 11-346, 11- 376, 11-392, 11-393, 11-448, 11-449, 11-450, 11-451, 11-454, 11-464, 11-465, 11-468, 11-470, 11-475, 11-477, 11-478, 11-479, 11-484, 11-485, 11-486, 11-491, 11-500, 11-502, 11-503, 11-506, 11-508, 11- 509, 11-511, 11-512, 11-513, 11-515, 11-517, 11-519, and 11-520 showed a control value of 100%.

[Test Example 4] Control test 2 against spider mite
Bean seedlings (second true leaf stage) cultivated in a plastic cup were placed on a turntable, and an emulsion diluted solution (5 ppm) prepared by applying the compound of the present invention according to Formulation Example 3 was sprayed uniformly with a spray gun. After spraying, placed in a constant temperature room at 25 ° C. (16 hours illumination), and 7 days later, 10 adult female spider mite were released on leaf discs cut out from the first true leaf and allowed to stand in a constant temperature room at 25 ° C. . Two days after the release, the number of female adults was examined, and the death rate (%) was calculated by the following formula (d). The test was carried out in two consecutive systems.

Test Example 4 is an investigation of the residual effect of the compound of the present invention against the spider mite. A 5 ppm emulsion diluent prepared by applying the compound of the present invention according to Formulation Example 3 was sprayed on a bean seedling (second true leaf stage) and allowed to stand for 7 days. Thereafter, 10 spider mites were released on leaf discs prepared by cutting out the first true leaves, and the number of live spider mites surviving two days after the release was examined. The residual effect was investigated by spraying the drug and confirming the control effect after standing for 7 days.

Table 15 below shows the results of a control test 2 against the spider mite using the compounds in the present specification. In Table 15 below, the compounds described in Reference Examples 1, 3, 5, 7, 13, 14, and 19 to 22 are the control values of 3.3 ppm emulsion diluent tested by the method according to Test Example 3 above. Since the control activity is further reduced 7 days after spraying, the control test 2 for the spider mite was not conducted.

"Summary of Test Example 4"
The compounds of Compound Nos. 2-209, 2-210, 2-447, and 2-448 shown in Examples 1 to 4 showed a very excellent mortality rate of 89.5% to 100%. High control activity was maintained even after days, and the residual effect was excellent.
The compounds of Reference Examples 1, 3, 5, and 7 having a slightly different molecular structure from the compound of Example 1 have a control activity against ticks in a 3.3 ppm emulsion diluted by the method according to Test Example 3 above. The control test 2 against the spider mite was not conducted because it was clear that the control activity after 7 days of spraying was further reduced.

Reference Example 2 using Compound No. 2-8 having a molecular structure in which R ^1a and R ^2a are different from the molecular structure of the compound of Example 2 in that R ^2a is a hydrogen atom Reference Example 4 using Compound No. 2-35 having a different molecular structure, Reference Example 8 using Compound No. 2-266 having a molecular structure in which R ^1a and R ^2a are both methyl groups The mortality was 27.8%, 8.2%, and 4.5%, respectively, which was lower than the mortality of 95.0% in Example 2 and inferior in residual efficacy.
In the molecular structure of the compound of Example 2, a molecule in which the fluorine atoms substituted at the 3, 4 and 5 positions of the benzene ring are changed to fluorine atoms substituted at the 3 and 4 positions, and the number of substitution of fluorine atoms is reduced by one. The death rate of Reference Example 6 using Compound No. 2-204 having a structure was 0%, and no residual effect was observed.

Reference Examples 9 and 10 using Compound Nos. 2-405 and 2-406 having different molecular structures of Examples 3 and 4 and different molecular structures in which R ^1a and R ^2a are both hydrogen atoms Although the insect ratios were 38.9% and 24.7%, and residual effects were observed, they were inferior to Examples 3 and 4 in which both the dead insect ratio was 100%.
Examples 1 and 2 using compounds having a molecular structure in which X ² is a fluorine atom have 89.5% and 95.0% mortality, respectively, and compounds having a molecular structure in which X ² is a chlorine atom are used. The death rates of Reference Examples 11 and 12 using Compound Nos. 2-557 and 2-558 having a molecular structure in which X ² is a bromine atom, whereas the death rates of both Examples 3 and 4 were 100%. The worm rates were 36.8% and 42.1%, respectively. Among the compounds in which X ² is a halogen atom, a compound in which X ² is a fluorine atom or a chlorine atom showed remarkably superior after-effect as compared with a compound in which X ² is a bromine atom.

The death rates of the compounds used in Reference Examples 15 to 18 described in Tables 15-2 and 15-3 were 10.6%, 47.7%, 15.0% and 12.5%, respectively. Compared with the compounds used in Examples 1 to 4, the mortality was low and the residual effect was poor. In Reference Examples 13, 14, and 19-22, the control test 2 against the spider mite was not performed because the control activity against mites at a concentration of 3.3 ppm tested by the method according to Test Example 3 was low.

Among the compounds shown in Table 15, the four compounds 2-209, 2-210, 2-447, and 2-448 exhibited very excellent mortality even after 7 days of spraying. It was confirmed that the difference in the structure caused a great difference in the residual effect.
These four compounds maintained high control activity even after 7 days of spraying, and showed very excellent residual effect. In addition, these four compounds greatly reduced the number of nymph mite individuals radiated 7 days after spraying in only 2 days, and were also excellent in rapid action.

From the above results, it was confirmed that the pest control agent according to the present invention is useful as a pest control agent in any of the above pests. In addition, it was confirmed that the compound represented by the formula (1-2) is particularly useful as an acaricide because it has both residual effect and rapid effect.

[Test Example 5] Pesticide control test 3
Ten adult female spider mites were released on each green seedling cultivated in a plastic cup. One day after the release, the kidney seedlings were placed on a turntable, and an emulsion diluted solution (3.3 ppm) prepared according to Formulation Example 3 was sprayed uniformly with a spray gun. After spraying, it was placed in a constant temperature room at 25 ° C. (16 hours illumination), and the number of female adults parasitized after 8 days of treatment was examined, and the control value (%) was calculated by the above formula (c). The test was carried out in two consecutive systems.

Test Example 5 is a control test for a spider mite that was performed at 500 ppm in Test Example 3 at a low concentration of 3.3 ppm. Table 16 below shows the results of the control test 3 against the spider mite using the compounds in the present specification.

As representative examples, the compound numbers 2-209, 2-210, 2-447, 2-448, 2-909, 2-910, 2-911, 2-912, 2-914, 2-915, 2-916 The compound of 2-920 showed a control value of 90% or more. As reference examples, the control values of the compounds Nos. 2-7, 2-8 and 2-727 were less than 60%.

[Test Example 6] Control test 4 against spider mite
Bean seedlings (second true leaf stage) cultivated in a plastic cup were placed on a turntable, and an emulsion diluted solution (5 ppm) prepared by applying the compound of the present invention according to Formulation Example 3 was sprayed uniformly with a spray gun. After spraying, placed in a constant temperature room at 25 ° C. (16 hours illumination), and 7 days later, 10 adult female spider mite were released on leaf discs cut out from the first true leaf and allowed to stand in a constant temperature room at 25 ° C. . Two days after the release, the number of adult females was examined, and the death rate (%) was calculated by the above formula (d). The test was carried out in two consecutive systems.

Test Example 6 is an investigation of the residual effect of the compound of the present invention against the spider mite. A 5 ppm emulsion diluent prepared by applying the compound of the present invention according to Formulation Example 3 was sprayed on a bean seedling (second true leaf stage) and allowed to stand for 7 days. Thereafter, 10 spider mites were released on leaf discs prepared by cutting out the first true leaves, and the number of live spider mites surviving two days after the release was examined. The residual effect was investigated by spraying the drug and confirming the control effect after standing for 7 days. Table 17 below shows the results of the control test 4 against the spider mite using the compounds in the present specification.

As representative examples, the compounds of compound Nos. 2-912, 2-914, 2-916, and 2-920 have a very excellent mortality rate of 86.8% to 100% and are highly controlled even after 7 days of spraying. The activity was maintained and the residual effect was excellent. As reference examples, the compound numbers 2-8, 2-35, 2-204, 2-266, 2-405, 2-406, 2-557, 2-558, 2-727, 2-728, 2-729 The death rate of the 2-730 compound was 0-42.1%.

[Test Example 7] Control test 5 against spider mite
A glass petri dish was filled with 0.3% undiluted agar, and 3 pieces of each 3 cm diameter bean leaf disk were placed. Ten adult female spider mites were released on each leaf disk. After the release, the emulsion diluted solution (1 ppm) prepared according to Formulation Example 3 was uniformly sprayed using an automatic spraying device (manufactured by Ikeda Rika). After spraying, it was placed in a constant temperature room at 25 ° C. (16 hours illumination), and the number of live insects was examined after 3 days, and the death rate (%) was calculated by the following formula (e). Table 18 below shows the results of the control test 5 against the spider mite using the compounds in the present specification.

As representative examples, the compounds Nos. 2-209, 2-210, 2-447, 2-448, and 2-920 showed a very excellent death rate of 84% to 100%. As a reference example, the mortality of the compounds Nos. 2-35, 2-266, 2-557, and 2-727 was 0 to 37%.

Since the substituted phenyl ether compound according to the present invention has an excellent control effect against pests, the use of this as a pest control agent can effectively control pests. In particular, the compound represented by the formula (1-2) has both a residual effect and a rapid effect on mites, and is useful as an active ingredient of an acaricide.

Since the N-substituted aniline compound according to the present invention has an excellent control effect against pests, the use of this as a pest control agent can effectively control pests.

Claims

Formula (1):

(In the formula (1), A represents a C 2 to C 5 haloalkyl group, a C 2 to C 5 haloalkenyl group, or an optionally substituted C 3 to C 8 cycloalkyl C 1 to C 4 alkyl group (the group is And may be mono-substituted or poly-substituted by a halogen atom or a C 1 -C 3 alkyl group.), N represents an integer of 0 to 2.
X 1 and X 2 are each independently a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 6 alkyl group that may be substituted with a halogen atom, or a C 1 -C 6 alkoxy that may be substituted with a halogen atom. Group, a C 3 -C 6 cycloalkyl group, or an aryl group which may be substituted with a halogen atom. However, if X 1 and X 2 all exhibited a hydrogen atom excluded.
Y is a hydrogen atom, a halogen atom, a nitro group, a cyano group, an amino group, a formyl group, an optionally C 1 ~ C 6 alkyl group optionally substituted by a halogen atom, which may C 1 be ~ C 6 alkoxy substituted with a halogen atom group, optionally substituted C 1 ~ C 6 alkylthio group with a halogen atom, a halogen atom with optionally substituted C 1 ~ C 6 alkylsulfinyl group, optionally substituted C 1 ~ C 6 alkylsulfonyl halogen atom Group, C 1 -C 6 alkylamino group, di-C 1 -C 6 alkylamino group, C 1 -C 6 alkylcarbonyl group, C 1 -C 6 alkoxycarbonyl group, C 1 -C 6 alkoxyiminomethyl group, halogen aryl group which may be substituted with atoms, an optionally substituted aryloxy group (in which a halogen atom, a cyano group, C 1 ~ C 3 alkyl group C 1 ~ C 3 haloalkyl group, C 1 ~ C 3 alkoxy group, C 1 ~ C 3 haloalkoxy group, C 1 ~ C 3 alkylthio group, C 1 ~ C 3 haloalkylthio group, C 1 ~ C 3 alkylsulfinyl group Monosubstituted by a C 1 -C 3 haloalkylsulfinyl group, a C 1 -C 3 alkylsulfonyl group, a C 1 -C 3 haloalkylsulfonyl group, a C 1 -C 3 alkylcarbonyl group, or a C 1 -C 3 alkoxycarbonyl group An optionally substituted arylthio group (this group is a halogen atom, a cyano group, a C 1 -C 3 alkyl group, a C 1 -C 3 haloalkyl group, a C 1 -C 3 alkoxy group, C 1 ~ C 3 haloalkoxy group, C 1 ~ C 3 alkylthio group, C 1 ~ C 3 haloalkylthio group, C 1 ~ C 3 Arukirusu Finiru group, C 1 ~ C 3 haloalkylsulfinyl group, a mono by C 1 ~ C 3 alkylsulfonyl group, C 1 ~ C 3 haloalkylsulfonyl group, C 1 ~ C 3 alkyl group or a C 1 ~ C 3 alkoxycarbonyl group, Substituted or polysubstituted.), Optionally substituted arylsulfinyl group (the group is a halogen atom, cyano group, C 1 -C 3 alkyl group, C 1 -C 3 haloalkyl group, C 1 -C 3) An alkoxy group, a C 1 -C 3 haloalkoxy group, a C 1 -C 3 alkylthio group, a C 1 -C 3 haloalkylthio group, a C 1 -C 3 alkylsulfinyl group, a C 1 -C 3 haloalkylsulfinyl group, a C 1- C 3 alkylsulfonyl group, C 1 -C 3 haloalkylsulfonyl group, C 1 -C 3 alkylcarbonyl group, Alternatively, it may be monosubstituted or polysubstituted by a C 1 -C 3 alkoxycarbonyl group. ), An optionally substituted arylsulfonyl group (the group is a halogen atom, a cyano group, a C 1 -C 3 alkyl group, a C 1 -C 3 haloalkyl group, a C 1 -C 3 alkoxy group, a C 1 -C 3 halo group) Alkoxy group, C 1 -C 3 alkylthio group, C 1 -C 3 haloalkylthio group, C 1 -C 3 alkylsulfinyl group, C 1 -C 3 haloalkylsulfinyl group, C 1 -C 3 alkylsulfonyl group, C 1- A C 3 haloalkylsulfonyl group, a C 1 -C 3 alkylcarbonyl group, or a C 1 -C 3 alkoxycarbonyl group may be mono- or polysubstituted), or a C 7 -C optionally substituted with a halogen atom 11 represents an aralkyloxy group, and m represents an integer of 1 to 5. When m represents an integer of 2 to 5, Y may be the same or different. Also, when referring to m is an integer of 2 or more, and bind adjacent each other in the Y, -OCH 2 O -, - OCF 2 O -, - OCH 2 CH 2 O -, - OCF 2 CH 2 O-, Alternatively, —OCF 2 CF 2 O— can also be shown.
R 1 and R 2 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a C 1 -C 6 alkyl group that may be substituted with a halogen atom, or a C 1 -C that may be substituted with a halogen atom. 4 represents an alkoxy group, a C 3 -C 6 cycloalkyl group, a C 1 -C 4 alkylcarbonyloxy group, or a benzoyloxy group, and p represents an integer of 1 to 5. When p represents an integer of 2 to 5, R 1 and R 2 on different carbon atoms may be the same or different. In addition, R 1 and R 2 on the same carbon atom can be each represented by (═O) or (═S) bonded to one oxygen atom or sulfur atom. Also, R 1 and R 2 on the same carbon atom can be bonded simultaneously to represent a C 1 -C 4 alkoxyimino group. R 1 and R 2 on the same carbon atom can be bonded to each other to form a 3-membered ring, 4-membered ring, 5-membered ring or 6-membered ring with 2 to 5 alkylene groups.
Z represents an oxygen atom, a sulfur atom, a sulfinyl group, or a sulfonyl group, and q represents an integer of 0 or 1. However, p and q cannot be 1 at the same time. )
The substituted phenyl ether compound characterized by these.
In the formula (1), A represents a C 2 -C 5 haloalkyl group, n represents an integer of 0 to 2,
X 1 and X 2 are each independently a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 6 alkyl group optionally substituted with a fluorine atom, a C 1 -C 6 alkoxy group, a cyclopropyl group, a cyclobutyl group , A cyclopentyl group, or a phenyl group (except when X 1 and X 2 both represent a hydrogen atom)
Y represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, an amino group, a C 1 -C 6 alkyl group which may be substituted with a halogen atom, a C 1 -C 4 alkoxy group which may be substituted with a halogen atom, C 1 ~ C 4 alkylthio group, C 1 ~ C 4 alkylsulfinyl group, C 1 ~ C 4 alkylsulfonyl group, C 1 ~ C 4 alkylamino group, di C 1 ~ C 4 alkylamino group, C 1 ~ C 4 alkyl A carbonyl group, a C 1 -C 4 alkoxycarbonyl group, a C 1 -C 4 alkoxyiminomethyl group, a phenyl group optionally substituted with a halogen atom, a phenoxy group optionally substituted with a halogen atom, or C 7 -C 11 Represents an aralkyloxy group, m represents an integer of 1 to 5, and when m represents an integer of 2 to 5, Y may be the same or different. When m represents an integer of 2 or more, and bind adjacent each other in the Y, to signify an -OCH 2 O-or -OCF 2 O-,
R 1 and R 2 are each independently a hydrogen atom, halogen atom, hydroxyl group, cyano group, C 1 -C 6 alkyl group, C 1 -C 4 alkoxy group, cyclopropyl group, cyclobutyl group, cyclopentyl group, C 1 -C 4 alkylcarbonyloxy group, or benzoyloxy group, p is any integer from 1 to 5, and when p is an integer from 2 to 5, R 1 and R 2 on different carbon atoms It may be the same or different, the same R 1 and R 2 located on the carbon atom bound to each one oxygen atom or a sulfur atom (= O) or (= S) and it can illustrated, the same R 1 and R 2 on the carbon atom can be simultaneously bonded to indicate a C 1 -C 4 alkoxyimino group, and R 1 and R 2 on the same carbon atom are bonded to each other to form 2 to 5 Can form a 3-membered ring, a 4-membered ring, a 5-membered ring and a 6-membered ring with an alkylene group of
Z represents an oxygen atom, a sulfur atom, a sulfinyl group, or a sulfonyl group, and q is an integer of 0 or 1 (provided that p and q cannot simultaneously be 1).
The substituted phenyl ether compound according to claim 1, wherein
In the formula (1), A is an optionally substituted C 3 -C 8 cycloalkyl C 1 -C 4 alkyl group (the group is mono- or poly-substituted by a halogen atom or a C 1 -C 3 alkyl group N may be any integer from 0 to 2,
X 1 and X 2 are each independently a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 6 alkyl group optionally substituted with a fluorine atom, a C 1 -C 6 alkoxy group, a cyclopropyl group, a cyclobutyl group , A cyclopentyl group, or a phenyl group (except when X 1 and X 2 both represent a hydrogen atom)
Y represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, an amino group, a C 1 -C 6 alkyl group which may be substituted with a halogen atom, a C 1 -C 4 alkoxy group which may be substituted with a halogen atom, C 1 ~ C 4 alkylthio group, C 1 ~ C 4 alkylsulfinyl group, C 1 ~ C 4 alkylsulfonyl group, C 1 ~ C 4 alkylamino group, di C 1 ~ C 4 alkylamino group, C 1 ~ C 4 alkyl A carbonyl group, a C 1 -C 4 alkoxycarbonyl group, a C 1 -C 4 alkoxyiminomethyl group, a phenyl group optionally substituted with a halogen atom, a phenoxy group optionally substituted with a halogen atom, or C 7 -C 11 Represents an aralkyloxy group, m represents an integer of 1 to 5, and when m represents an integer of 2 to 5, Y may be the same or different. When m represents an integer of 2 or more, and bind adjacent each other in the Y, to signify an -OCH 2 O-or -OCF 2 O-,
R 1 and R 2 are each independently a hydrogen atom, halogen atom, hydroxyl group, cyano group, C 1 -C 6 alkyl group, C 1 -C 4 alkoxy group, cyclopropyl group, cyclobutyl group, cyclopentyl group, C 1 -C 4 alkylcarbonyloxy group, or benzoyloxy group, p is any integer from 1 to 5, and when p is an integer from 2 to 5, R 1 and R 2 on different carbon atoms It may be the same or different, the same R 1 and R 2 located on the carbon atom bound to each one oxygen atom or a sulfur atom (= O) or (= S) and it can illustrated, the same R 1 and R 2 on the carbon atom can be simultaneously bonded to indicate a C 1 -C 4 alkoxyimino group, and R 1 and R 2 on the same carbon atom are bonded to each other to form 2 to 5 Can form a 3-membered ring, a 4-membered ring, a 5-membered ring and a 6-membered ring with an alkylene group of
Z represents an oxygen atom, a sulfur atom, a sulfinyl group, or a sulfonyl group, and q is an integer of 0 or 1 (provided that p and q cannot simultaneously be 1).
The substituted phenyl ether compound according to claim 1, wherein
In the formula (1), A represents a C 2 -C 5 haloalkyl group, n represents an integer of 0 to 2,
X 1 represents a halogen atom, a C 1 -C 4 alkyl group, or a methoxy group,
X 2 represents a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 4 alkyl group which may be substituted with a fluorine atom, a methoxy group, a cyclopropyl group, or a phenyl group,
Y represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, an amino group, a C 1 -C 4 alkyl group which may be substituted with a halogen atom, a C 1 -C 4 alkoxy group which may be substituted with a halogen atom, C 1 ~ C 4 alkylthio group, C 1 ~ C 4 alkylsulfinyl group, C 1 ~ C 4 alkylsulfonyl group, C 1 ~ C 4 alkylamino group, di C 1 ~ C 4 alkylamino group, C 1 ~ C 4 alkoxy A carbonyl group, a C 1 -C 4 alkoxyiminomethyl group, or a phenoxy group which may be substituted with a halogen atom, m represents an integer of 1 to 5, and m represents an integer of 2 to 5 , Y may be the same or different, and when m represents an integer of 2 or more, adjacent Ys may be bonded to each other to represent —OCH 2 O— or —OCF 2 O—. Can
R 1 and R 2 are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a hydroxyl group, a C 1 -C 6 alkyl group, a C 1 -C 4 alkoxy group, or a C 1 -C 4 alkylcarbonyloxy And p represents an integer of 1 to 3, and when p represents an integer of 2 or 3, R 1 and R 2 on different carbon atoms may be the same or different, and R 1 and R 2 on the carbon atom can each be bonded to one oxygen atom to indicate (= O), and R 1 and R 2 on the same carbon atom can be bonded simultaneously to form C 1 It may also indicate ~ C 4 alkoxyimino group. R 1 and R 2 on the same carbon atom can be bonded to each other to form a 3-membered, 4-membered, 5-membered or 6-membered ring with 2 to 5 alkylene groups;
Z represents an oxygen atom, and q is an integer of either 0 or 1 (provided that p and q cannot simultaneously be 1).
The substituted phenyl ether compound according to claim 1, wherein
In the formula (1), A is an optionally substituted C 3 -C 8 cycloalkyl C 1 -C 4 alkyl group (the group is mono- or poly-substituted by a halogen atom or a C 1 -C 3 alkyl group N may be any integer from 0 to 2,
X 1 represents a halogen atom, a C 1 -C 4 alkyl group, or a methoxy group,
X 2 represents a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 4 alkyl group which may be substituted with a fluorine atom, a methoxy group, a cyclopropyl group, or a phenyl group,
Y represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, an amino group, a C 1 -C 4 alkyl group which may be substituted with a halogen atom, a C 1 -C 4 alkoxy group which may be substituted with a halogen atom, C 1 ~ C 4 alkylthio group, C 1 ~ C 4 alkylsulfinyl group, C 1 ~ C 4 alkylsulfonyl group, C 1 ~ C 4 alkylamino group, di C 1 ~ C 4 alkylamino group, C 1 ~ C 4 alkoxy A carbonyl group, a C 1 -C 4 alkoxyiminomethyl group, or a phenoxy group which may be substituted with a halogen atom, m represents an integer of 1 to 5, and m represents an integer of 2 to 5 , Y may be the same or different, and when m represents an integer of 2 or more, adjacent Ys may be bonded to each other to represent —OCH 2 O— or —OCF 2 O—. Can
R 1 and R 2 are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a hydroxyl group, a C 1 -C 6 alkyl group, a C 1 -C 4 alkoxy group, or a C 1 -C 4 alkylcarbonyloxy And p represents an integer of 1 to 3, and when p represents an integer of 2 or 3, R 1 and R 2 on different carbon atoms may be the same or different, and R 1 and R 2 on the carbon atom can each be bound to one oxygen atom and represented as (═O). Also, R 1 and R 2 on the same carbon atom can be bonded at the same time to indicate a C 1 -C 4 alkoxyimino group, and R 1 and R 2 on the same carbon atom are bonded to each other, 2- to 5-alkylene groups can form 3-, 4-, 5- and 6-membered rings,
Z represents an oxygen atom, and q is an integer of either 0 or 1 (provided that p and q cannot simultaneously be 1).
The substituted phenyl ether compound according to claim 1, wherein
In the formula (1), A represents a 2,2,2-trifluoroethyl group, n represents an integer of 0 or 1,
X 1 represents a halogen atom or a C 1 -C 4 alkyl group,
X 2 represents a halogen atom, a cyano group, or a C 1 -C 4 alkyl group which may be substituted with a fluorine atom,
Y represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a C 1 -C 4 alkyl group which may be substituted with a halogen atom, a C 1 -C 4 alkoxy group which may be substituted with a halogen atom, C 1 -C 4 represents an alkylthio group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, or a phenoxy group which may be substituted with a halogen atom, m represents an integer of 1 to 5, m When Y represents an integer of 2 to 5, Y may be the same or different, and when m represents an integer of 2 or more, adjacent Ys may be bonded to each other to represent —OCF 2 O—. Can
R 1 and R 2 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a hydroxyl group, a C 1 -C 6 alkyl group, or a C 1 -C 4 alkoxy group, and p is 1 to 3 When any integer is shown and p is an integer of 2 or 3, R 1 and R 2 on different carbon atoms may be the same or different, and R 1 and R 2 on the same carbon atom Can be each represented by (═O) bonded to one oxygen atom, R 1 and R 2 on the same carbon atom are bonded to each other, and a cyclopropane ring, a cyclobutane ring, Can form a cyclopentane ring and a cyclohexane ring,
Z represents an oxygen atom, and q is an integer of either 0 or 1 (provided that p and q cannot simultaneously be 1).
The substituted phenyl ether compound according to claim 1, wherein
In the formula (1), A represents a cyclopropylmethyl group, n represents an integer of 0 or 1,
X 1 represents a halogen atom or a C 1 -C 4 alkyl group,
X 2 represents a halogen atom, a cyano group, or a C 1 -C 4 alkyl group which may be substituted with a fluorine atom,
Y represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a C 1 -C 4 alkyl group which may be substituted with a halogen atom, a C 1 -C 4 alkoxy group which may be substituted with a halogen atom, C 1 -C 4 represents an alkylthio group, a C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, or a phenoxy group which may be substituted with a halogen atom, m represents an integer of 1 to 5, m When Y represents an integer of 2 to 5, Y may be the same or different, and when m represents an integer of 2 or more, adjacent Ys may be bonded to each other to represent —OCF 2 O—. Can
R 1 and R 2 each independently represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a hydroxyl group, a C 1 -C 6 alkyl group, or a C 1 -C 4 alkoxy group, and p is 1 to 3 When any integer is shown and p is an integer of 2 or 3, R 1 and R 2 on different carbon atoms may be the same or different, and R 1 and R 2 on the same carbon atom Can be each represented by (═O) bonded to one oxygen atom, R 1 and R 2 on the same carbon atom are bonded to each other, and a cyclopropane ring, a cyclobutane ring, Can form a cyclopentane ring and a cyclohexane ring,
Z represents an oxygen atom, and q is an integer of either 0 or 1 (provided that p and q cannot simultaneously be 1).
The substituted phenyl ether compound according to claim 1, wherein
Formula (1a):

(Formula (1a) shows the formula (1) when q is 0 and p is 2. In this case, R 1 can be represented by R 1a and R 1b , and R 2 can be represented by R 2a And R 2b .
In the formula (1a), A represents a 2,2,2-trifluoroethyl group, and n represents an integer of 0 or 1.
X 1 represents a halogen atom or a C 1 -C 4 alkyl group.
X 2 represents a halogen atom, a cyano group, or a C 1 -C 4 alkyl group which may be substituted with a fluorine atom.
Y is a halogen atom, a nitro group, a cyano group, optionally substituted C 1 ~ C 4 alkyl group by a halogen atom, optionally substituted C 1 ~ C 4 alkoxy group with a halogen atom, C 1 ~ C 4 alkylthio groups , A C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, or a phenoxy group that may be substituted with a halogen atom, m represents an integer of 1 to 5. When m represents an integer of 2 to 5, Y may be the same or different. When m represents an integer of 2 or more, adjacent Ys can be bonded to each other to represent —OCF 2 O—.
R 1a and R 2a each independently represent a fluorine atom, a chlorine atom, or a bromine atom. Further, R 1a and R 2a on the same carbon atom can each be bonded to one oxygen atom and represented as (═O).
R 1b and R 2b each independently represent a hydrogen atom or a C 1 -C 4 alkyl group. )
The substituted phenyl ether compound according to claim 1, wherein
In the formula (1a), A represents a cyclopropylmethyl group, n represents an integer of 0 or 1,
X 1 represents a halogen atom or a C 1 -C 4 alkyl group,
X 2 represents a halogen atom, a cyano group, or a C 1 -C 4 alkyl group which may be substituted with a fluorine atom,
Y is a halogen atom, a nitro group, a cyano group, optionally substituted C 1 ~ C 4 alkyl group by a halogen atom, optionally substituted C 1 ~ C 4 alkoxy group with a halogen atom, C 1 ~ C 4 alkylthio groups , A C 1 -C 4 alkylsulfinyl group, a C 1 -C 4 alkylsulfonyl group, or a phenoxy group optionally substituted with a halogen atom, m represents an integer of 1 to 5, When Y represents an integer of 5, Y may be the same or different, and when m represents an integer of 2 or more, adjacent Ys may be bonded to each other to represent —OCF 2 O—,
R 1a and R 2a each independently represent a fluorine atom, a chlorine atom, or a bromine atom, and R 1a and R 2a on the same carbon atom are each bonded to one oxygen atom and represented as (═O). It is possible,
The substituted phenyl ether compound according to claim 8, wherein R 1b and R 2b are each independently represented by a hydrogen atom or a C 1 -C 4 alkyl group.
Formula (2):

(In Formula (2), A is an optionally substituted C 3 -C 8 cycloalkylmethyl group (the group may be mono-substituted or poly-substituted by a fluorine atom or a C 1 -C 3 alkyl group). N represents an integer of either 0 or 1.
X 1 represents a C 1 -C 4 alkyl group, and X 2 represents a hydrogen atom, a halogen atom, or a C 1 -C 4 alkyl group. )
The phenol compound which is a manufacturing intermediate of the substituted phenyl ether compound according to any one of claims 1 to 9, wherein
In the formula (2), A represents a cyclopropylmethyl group, n represents an integer of 0 or 1,
The phenol compound according to claim 10, wherein X 1 represents a C 1 -C 4 alkyl group, and X 2 is represented by a halogen atom.
A pest control agent comprising the substituted phenyl ether compound according to any one of claims 1 to 9 as an active ingredient.
An insecticide or acaricide containing the substituted phenyl ether compound according to any one of claims 1 to 9 as an active ingredient.
Formula (1-3):

(In the formula (1-3), q is 0, and one of Y may be substituted with a phenoxy group, an optionally substituted phenylthio group, an optionally substituted phenylsulfinyl group, or an optionally substituted group. The formula (1) when it is a good phenylsulfonyl group is shown.
In the formula (1-3), A represents a C 2 -C 5 haloalkyl group, a C 2 -C 5 haloalkenyl group, or an optionally substituted C 3 -C 8 cycloalkyl C 1 -C 4 alkyl group (this group Represents a mono- or poly-substitution with a halogen atom or a C 1 -C 3 alkyl group, and n represents an integer of 0 to 2.
X 1 and X 2 are each independently a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 6 alkyl group that may be substituted with a halogen atom, or a C 1 -C 6 alkoxy that may be substituted with a halogen atom. Group, a C 3 -C 6 cycloalkyl group, or an aryl group which may be substituted with a halogen atom. However, if X 1 and X 2 all exhibited a hydrogen atom excluded.
Y represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a formyl group, a C 1 -C 6 alkyl group which may be substituted with a halogen atom, a C 1 -C 6 alkoxy group which may be substituted with a halogen atom, a halogen optionally substituted C 1 ~ C 6 alkylthio group, a halogen atom with optionally substituted C 1 ~ C 6 alkylsulfinyl group, optionally substituted C 1 ~ C 6 alkylsulfonyl group by a halogen atom, C 1 to C 6 alkylcarbonyl group, C 1 to C 6 alkoxycarbonyl group, C 1 to C 6 alkoxyiminomethyl group, aryl group optionally substituted with a halogen atom, or C 7 to optionally substituted with a halogen atom C 11 represents an aralkyloxy group, and m represents an integer of 2 to 5. When m represents an integer of 3 to 5, Y may be the same or different.
R 1 and R 2 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a C 1 -C 6 alkyl group that may be substituted with a halogen atom, or a C 1 -C that may be substituted with a halogen atom. 4 represents an alkoxy group, a C 3 -C 6 cycloalkyl group, a C 1 -C 4 alkylcarbonyloxy group, or a benzoyloxy group, and p represents an integer of 1 or 2. When p is 2, R 1 and R 2 on different carbon atoms may be the same or different. Further, R 1 and R 2 on the same carbon atom can each be bonded to one oxygen atom and represented as (═O). Also, R 1 and R 2 on the same carbon atom can be bonded simultaneously to represent a C 1 -C 4 alkoxyimino group. R 1 and R 2 on the same carbon atom can be bonded to each other to form a 3-membered ring, 4-membered ring, 5-membered ring or 6-membered ring with 2 to 5 alkylene groups.
Z 1 represents an oxygen atom, a sulfur atom, a sulfinyl group, or a sulfonyl group.
Y 1 is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a C 1 -C 3 alkyl group that may be substituted with a halogen atom, a C 1 -C 3 alkoxy group that may be substituted with a halogen atom, or a halogen atom optionally substituted C 1 ~ C 3 alkylthio group, C 1 ~ C 3 alkyl sulfates which may be substituted by a halogen atom alkylsulfonyl group, ~ C 1 may be substituted with halogen atoms C 3 alkylsulfonyl group, C 1 ~ A C 3 alkylcarbonyl group or a C 1 -C 3 alkoxycarbonyl group, and r represents an integer of 1 to 5. When r represents an integer of 2 to 5, Y 1 may be the same or different. )
The substituted phenyl ether compound characterized by these.
In the formula (1-3), A represents a C 2 -C 5 haloalkyl group or a cyclopropylmethyl group, n represents an integer of 0 to 2,
X 1 and X 2 each independently represent a hydrogen atom, a halogen atom, or a C 1 -C 6 alkyl group (except when both X 1 and X 2 represent a hydrogen atom).
Y is a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl group that may be substituted with a halogen atom, a C 1 -C 6 alkoxy group that may be substituted with a halogen atom, or a C 1 that may be substituted with a halogen atom. ~ C 6 alkylthio group, a halogen atom with optionally substituted C 1 ~ C 6 alkylsulfinyl group or by C 1 may be ~ C 6 alkylsulfonyl group substituted with a halogen atom,, m is either 2 from 5 And when m represents an integer of 3 to 5, Y may be the same or different,
R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, or a hydroxyl group, p represents an integer of 1 or 2, and when p is 2, R 1 and R on different carbon atoms R 2 may be the same or different, and R 1 and R 2 on the same carbon atom may each be bonded to one oxygen atom to indicate (═O);
Z 1 represents an oxygen atom, a sulfur atom, a sulfinyl group, or a sulfonyl group,
Y 1 is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a C 1 -C 3 alkyl group that may be substituted with a halogen atom, a C 1 -C 3 alkoxy group that may be substituted with a halogen atom, or a halogen atom optionally substituted C 1 ~ C 3 alkylthio group, C 1 ~ C 3 alkyl sulfates which may be substituted by a halogen atom alkylsulfonyl group, ~ C 1 may be substituted with halogen atoms C 3 alkylsulfonyl group, C 1 ~ A C 3 alkylcarbonyl group or a C 1 -C 3 alkoxycarbonyl group, r is an integer of 1 to 3, and when r is an integer of 2 or 3, Y 1 is the same or different. May be.
The substituted phenyl ether compound according to claim 14, which is represented by:
Formula (1-4):

(In the formula (1-4), one of Y is a phenoxy group which may be substituted at the 4-position on the benzene ring, an optionally substituted phenylthio group, an optionally substituted phenylsulfinyl group, or an optionally substituted group. The formula (1-3) when it is a good phenylsulfonyl group is shown.
In formula (1-4), A represents a 2,2,2-trifluoroethyl group or a cyclopropylmethyl group, and n represents an integer of 0 or 1.
X 1 represents a C 1 -C 3 alkyl group, and X 2 represents a halogen atom.
Y represents a hydrogen atom, a halogen atom, or a C 1 -C 3 alkyl group which may be substituted with a halogen atom, and m represents an integer of 2 or 3. When m is 3, Y may be the same or different.
R 1 and R 2 are each independently a hydrogen atom, a halogen atom or a hydroxyl group,, p represents an integer of 1 or 2. When p is 2, R 1 and R 2 on different carbon atoms may be the same or different. Further, R 1 and R 2 on the same carbon atom can each be bonded to one oxygen atom and represented as (═O).
Z 1 represents an oxygen atom, a sulfur atom, or a sulfinyl group.
Y 1 is a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 3 alkyl group that may be substituted with a halogen atom, a C 1 -C 3 alkoxy group that may be substituted with a halogen atom, or a halogen atom. A C 1 -C 3 alkylthio group which may be substituted, or a C 1 -C 3 alkylsulfinyl group which may be substituted with a halogen atom, and r represents an integer of 1 to 3. When r represents an integer of 2 or 3, Y 1 may be the same or different. )
The substituted phenyl ether compound characterized by these.
Formula (1-5):

(Formula (1-5), q is 0, m is an integer of 2 or more, attached adjacent Y each other, -OCH 2 O -, - OCF 2 O -, - OCH 2 CH The formula (1) in the case of 2 O—, —OCF 2 CH 2 O—, or —OCF 2 CF 2 O— is shown.
In the formula (1-5), A represents a C 2 -C 5 haloalkyl group, a C 2 -C 5 haloalkenyl group, or an optionally substituted C 3 -C 8 cycloalkyl C 1 -C 4 alkyl group (this group Can be mono- or poly-substituted by halogen atoms or C 1 -C 3 alkyl groups)
n represents an integer of 0 to 2.
X 1 and X 2 are each independently a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 6 alkyl group that may be substituted with a halogen atom, or a C 1 -C 6 alkoxy that may be substituted with a halogen atom. Group, a C 3 -C 6 cycloalkyl group, or an aryl group which may be substituted with a halogen atom. However, if X 1 and X 2 all exhibited a hydrogen atom excluded.
Y represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a formyl group, a C 1 -C 6 alkyl group which may be substituted with a halogen atom, a C 1 -C 6 alkoxy group which may be substituted with a halogen atom, a halogen optionally substituted C 1 ~ C 6 alkylthio group, a halogen atom with optionally substituted C 1 ~ C 6 alkylsulfinyl group, optionally substituted C 1 ~ C 6 alkylsulfonyl group by a halogen atom, C 1 to C 6 alkylcarbonyl group, C 1 to C 6 alkoxycarbonyl group, C 1 to C 6 alkoxyiminomethyl group, aryl group optionally substituted with a halogen atom, or C 7 to optionally substituted with a halogen atom C 11 represents an aralkyloxy group, and m represents an integer of 3 to 5. When m represents an integer of 4 or 5, Y may be the same or different.
R 1 and R 2 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a C 1 -C 6 alkyl group that may be substituted with a halogen atom, or a C 1 -C that may be substituted with a halogen atom. 4 represents an alkoxy group, a C 3 -C 6 cycloalkyl group, a C 1 -C 4 alkylcarbonyloxy group, or a benzoyloxy group, and p represents an integer of 1 or 2. When p is 2, R 1 and R 2 on different carbon atoms may be the same or different. Further, R 1 and R 2 on the same carbon atom can each be bonded to one oxygen atom and represented as (═O). Also, R 1 and R 2 on the same carbon atom can be bonded simultaneously to represent a C 1 -C 4 alkoxyimino group. R 1 and R 2 on the same carbon atom can be bonded to each other to form a 3-membered ring, 4-membered ring, 5-membered ring or 6-membered ring with 2 to 5 alkylene groups.
Y 2 represents a hydrogen atom or a fluorine atom, and t represents an integer of 1 or 2. When t is 2, Y 2 may be the same or different. )
The substituted phenyl ether compound characterized by these.
In the formula (1-5), A represents a C 2 -C 5 haloalkyl group or a cyclopropylmethyl group, n represents an integer of 0 to 2,
X 1 and X 2 each independently represent a hydrogen atom, a halogen atom, or a C 1 -C 6 alkyl group (except when both X 1 and X 2 represent a hydrogen atom).
Y represents a hydrogen atom, a halogen atom, or a C 1 -C 6 alkyl group that may be substituted with a halogen atom, m represents an integer of 3 to 5, and m represents an integer of 4 or 5 , Y may be the same or different,
R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, or a hydroxyl group, p represents an integer of 1 or 2, and when p is 2, R 1 and R on different carbon atoms R 2 may be the same or different, and R 1 and R 2 on the same carbon atom may each be bonded to one oxygen atom to indicate (═O);
Y 2 represents a hydrogen atom or a fluorine atom, and t is 1
The substituted phenyl ether compound according to claim 17, wherein
In the formula (1-5), A represents a 2,2,2-trifluoroethyl group or a cyclopropylmethyl group, n represents an integer of 0 to 1,
X 1 represents a C 1 -C 3 alkyl group, X 2 represents a halogen atom,
Y represents a hydrogen atom, m represents an integer of 3 to 5,
R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, or a hydroxyl group, p represents an integer of 1 or 2, and when p is 2, R 1 and R on different carbon atoms R 2 may be the same or different, and R 1 and R 2 on the same carbon atom may each be bonded to one oxygen atom to indicate (═O);
Y 2 represents a fluorine atom, and t is 1
The substituted phenyl ether compound according to claim 17, wherein
A pest control agent comprising the substituted phenyl ether compound according to any one of claims 14 to 19 as an active ingredient.
An insecticide or acaricide comprising the substituted phenyl ether compound according to any one of claims 14 to 19 as an active ingredient.
Formula (1-6):

(In the formula (1-6), A 100 represents a C 2 to C 5 haloalkyl group or a C 3 to C 6 cycloalkyl C 1 to C 3 alkyl group, and n represents an integer of 0 to 2) .
X 101 and X 102 are each independently a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 6 alkyl group that may be substituted with a halogen atom, or a C 1 -C 6 that may be substituted with a halogen atom. An alkoxy group is shown. However, X 101 and X 102 cannot simultaneously be hydrogen atoms.
Y 100 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a formyl group, a C 1 -C 6 alkyl group that may be substituted with a halogen atom, a C 1 -C 6 alkoxy group that may be substituted with a halogen atom, optionally substituted C 1 ~ C 6 alkylthio group with a halogen atom, a halogen atom with optionally substituted C 1 ~ C 6 alkylsulfinyl group, optionally substituted C 1 ~ C 6 alkylsulfonyl group with a halogen atom, A C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxycarbonyl group, or a C 1 -C 6 alkoxyiminomethyl group, and v represents an integer of 1 to 4. When v represents an integer of 2 to 4, Y 100 may be the same or different.
R 101a and R 102a are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, an optionally C 1 ~ C 6 alkyl group optionally substituted by a halogen atom or C 1 ~ optionally substituted by a halogen atom, It shows the C 4 alkoxy groups. Further, R 101a and R 102a on the same carbon atom can be each represented by (═O) or (═S) by being bonded to one oxygen atom or sulfur atom. Also, R 101a and R 102a on the same carbon atom can be bonded simultaneously to represent a C 1 -C 4 alkoxyimino group. R 101a and R 102a on the same carbon atom can be bonded to each other to form a 3-membered ring, 4-membered ring, 5-membered ring or 6-membered ring with 2 to 5 alkylene groups.
R 101b and R 102b each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl group that may be substituted with a halogen atom, or a C 1 -C 4 alkoxy group that may be substituted with a halogen atom. U represents an integer of either 0 or 1.
W 1 is a C 2 to C 6 alkenyl group which may be substituted with a halogen atom, a C 2 to C 6 alkynyl group which may be substituted with a halogen atom, a C 3 to C 6 cycloalkyl group, or a C 3 to C 6 cyclo group. Alkyl C 1 -C 3 alkyl group, formyl group, C 1 -C 6 alkylcarbonyl group optionally substituted with halogen atom, C 2 -C 6 alkenylcarbonyl group optionally substituted with halogen atom, substituted with halogen atom A C 2 -C 6 alkynylcarbonyl group which may be substituted, a C 3 -C 6 cycloalkylcarbonyl group which may be substituted with a halogen atom, a C 3 -C 6 cycloalkyl which may be substituted with a halogen atom, C 1 -C 3 alkyl group which may be substituted by a halogen atom C 1 ~ C 6 alkoxycarbonyl group which may be substituted by a halogen atom C ~ C 6 alkenyloxycarbonyl group, optionally substituted C 2 be ~ C 6 alkynyloxy group with a halogen atom, optionally substituted C 3 be ~ C 6 cycloalkyloxy group with a halogen atom, is substituted with a halogen atom An optionally substituted C 3 -C 6 cycloalkyl C 1 -C 3 alkyloxycarbonyl group, an optionally substituted C 1 -C 6 alkylaminocarbonyl group, an optionally substituted di-C 1- C 6 alkylaminocarbonyl group, C 3 -C 6 cycloalkylaminocarbonyl group optionally substituted with a halogen atom, C 3 -C 6 cycloalkyl C 1 -C 3 alkylaminocarbonyl group optionally substituted with a halogen atom , which may be substituted by a halogen atom C 1 ~ C 6 alkylsulfonyl group, halogen May be substituted with atoms C 3 ~ C 6 cycloalkyl alkylsulfonyl group which may be substituted by a halogen atom C 3 ~ C 6 cycloalkyl C 1 ~ C 3 alkylsulfonyl group which may be substituted by a halogen atom C A 1 to C 6 alkylaminosulfonyl group, a di C 1 to C 6 alkylaminosulfonyl group which may be substituted with a halogen atom, an aryl group which may be substituted with a halogen atom, a benzyl group which may be substituted with a halogen atom, An arylcarbonyl group optionally substituted with a halogen atom, a benzylcarbonyl group optionally substituted with a halogen atom, an aryloxycarbonyl group optionally substituted with a halogen atom, a benzyloxycarbonyl group optionally substituted with a halogen atom, Arylaminocarbonyl group optionally substituted with halogen atoms, substituted An arylsulfonyl group (in which also may be mono-substituted or poly-substituted by halogen atom or C 1 ~ C 3 alkyl group. ), Or a benzylsulfonyl group which may be substituted with a halogen atom.
W 2 is a hydrogen atom, a C 1 to C 6 alkyl group that may be substituted with a halogen atom, a C 2 to C 6 alkenyl group that may be substituted with a halogen atom, or a C 2 to C that may be substituted with a halogen atom. 6 alkynyl groups, C 3 -C 6 cycloalkyl groups, C 1 -C 6 alkoxy C 1 -C 3 alkyl groups, C 1 -C 6 alkylcarbonyl groups optionally substituted with halogen atoms, substituted with halogen atoms A C 1 -C 6 alkoxycarbonyl group, a C 1 -C 6 alkylsulfonyl group which may be substituted with a halogen atom, a benzyl group which may be substituted with a halogen atom, or an arylcarbonyl group which may be substituted with a halogen atom Or an arylsulfonyl group which may be substituted (the group is mono- or poly-substituted by a halogen atom or a C 1 -C 3 alkyl group) May be.) )
An N-substituted aniline compound represented by the formula:
In the formula (1-6), A 100 represents a 2,2,2-trifluoroethyl group or a cyclopropylmethyl group, n represents an integer of 0 or 1,
X 101 represents a C 1 -C 6 alkyl group,
X 102 represents a hydrogen atom, a halogen atom, or a C 1 -C 6 alkyl group,
Y 100 represents a hydrogen atom, a halogen atom, or a C 1 -C 6 alkyl group which may be substituted with a halogen atom, v represents an integer of 1 or 2, and when v is 2, Y 100 is May be the same or different,
R 101a and R 102a each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, or a C 1 -C 6 alkyl group that may be substituted with a halogen atom, and R 101a and R 102a on the same carbon atom are Each bonded to one oxygen atom can be shown as (= O),
R 101b and R 102b represent a hydrogen atom, u represents an integer of 0 or 1,
W 1 is a C 1 -C 6 alkylcarbonyl group, C 3 -C 6 cycloalkylcarbonyl group optionally substituted with a halogen atom, a C 1 -C 6 alkoxycarbonyl group optionally substituted with a halogen atom, C 3- C 6 cycloalkyloxycarbonyl group, C 1 -C 6 alkylaminocarbonyl group, C 1 -C 6 alkylsulfonyl group optionally substituted with a halogen atom, phenyl group optionally substituted with a halogen atom, substituted with a halogen atom A benzoyl group which may be substituted with a halogen atom, a benzyloxycarbonyl group which may be substituted with a halogen atom, a phenylaminocarbonyl group which may be substituted with a halogen atom, or a substituent A good phenylsulfonyl group (which is a halogen atom or a C 1 -C 3 And may be mono- or poly-substituted by an alkyl group)
W 2 is a hydrogen atom, C 1 ~ C 6 alkyl group, a halogen atom optionally substituted C 1 ~ C 6 alkyl group, optionally substituted C 1 ~ C 6 alkoxycarbonyl group with a halogen atom, a halogen atom A C 1 -C 6 alkylsulfonyl group optionally substituted with, a benzyl group, a benzoyl group optionally substituted with a halogen atom, or a phenylsulfonyl group optionally substituted (the group is a halogen atom, or C 1 -C (It may be mono-substituted or poly-substituted by 3 alkyl groups.)
The N-substituted aniline compound according to claim 22, wherein
In the formula (1-6), A 100 represents a 2,2,2-trifluoroethyl group or a cyclopropylmethyl group, n represents an integer of 0 or 1,
X 101 represents a C 1 -C 4 alkyl group,
X 102 represents a halogen atom,
Y 100 represents a hydrogen atom or a halogen atom, v represents an integer of 1 or 2, and when v is 2, Y 100 may be the same or different,
R 101a and R 102a each independently represent a hydrogen atom, a halogen atom, or a hydroxyl group, and R 101a and R 102a on the same carbon atom are each bonded to one oxygen atom to indicate (= O). Can
R 101b and R 102b represent a hydrogen atom, u represents an integer of 0 or 1,
W 1 represents a C 1 -C 6 alkylcarbonyl group, a C 3 -C 6 cycloalkylcarbonyl group optionally substituted with a halogen atom, a C 1 -C 6 alkoxycarbonyl group optionally substituted with a halogen atom, a halogen atom A phenylsulfonyl group that may be substituted with an optionally substituted C 1 -C 6 alkylsulfonyl group, a benzoyl group, or a C 1 -C 3 alkyl group;
W 2 is a hydrogen atom, C 1 ~ C 6 alkyl group, a halogen atom optionally substituted C 1 ~ C 6 alkyl group, optionally substituted C 1 ~ C 6 alkoxycarbonyl group with a halogen atom, a halogen atom The N-substituted aniline compound according to claim 22, which is a phenylsulfonyl group which may be substituted with a C 1 -C 6 alkylsulfonyl group, a benzoyl group, or a C 1 -C 3 alkyl group which may be substituted with.
A pest control agent comprising the N-substituted aniline compound according to any one of claims 22 to 24 as an active ingredient.
An insecticide or acaricide comprising the N-substituted aniline compound according to any one of claims 22 to 24 as an active ingredient.
Formula (3):

(In Formula (3), G represents CO 2 R 3 (R 103 represents a C 1 -C 4 alkyl group), or CH 2 OR 104 (R 104 represents a hydrogen atom or a C atom optionally substituted with a halogen atom). 1 -C 4 alkylsulfonyl group, or arylsulfonyl group optionally substituted with C 1 -C 4 alkyl group.
Y 101 and Y 102 each independently represent a hydrogen atom (except when G represents CO 2 R 103 ), a halogen atom, or a C 1 -C 4 alkyl group that may be substituted with a halogen atom. .
W 103 and W 104 each independently represent a hydrogen atom, a C 1 -C 6 alkylcarbonyl group that may be substituted with a halogen atom, a C 1 -C 6 alkoxycarbonyl group, or a C that may be substituted with a halogen atom. 1 to C 6 alkylsulfonyl group. )
An aniline compound.
Formula (1-2):

(In the formula (1-2), n represents an integer of 0 or 1.
X 2 represents a fluorine atom or a chlorine atom. )
A substituted phenyl ether compound represented by the formula:
An acaricide comprising the substituted phenyl ether compound according to claim 28 as an active ingredient.