JP2020059686A - Novel 1-phenylpiperidine derivative, and horticultural agent containing the same as active ingredient - Google Patents

Abstract

To provide a novel horticultural agent.SOLUTION: There are provided a 1-phenylpiperidine derivative represented by (1), in which R:Calkyl group haloalkyl group, Calkenyl group, haloalkenyl group, alkynyl group, haloalkynyl group, Ccycloalkyl Calkyl group or Chalocycloalkyl Calkyl group, X:Calkyl group, haloalkyl group, Ccycloalkyl group, Calkenyl group, alkynyl group, haloalkenyl group, haloalkynyl group, Calkoxy group, haloalkoxy group, Chalocycloalkyl group, Calkyloxycarbonyl group, hydroxyalkyl group, Calkoxy Calkyl group, formyl group, halogen, cyano group or nitro group, Y:hydrogen, halogen, Calkyl group, haloalkyl group, Z:may be same or different, and Calkyl group, n:0 to 1, m:1 to 3, and N-oxide thereof.SELECTED DRAWING: None

Description

  TECHNICAL FIELD The present invention relates to a novel 1-phenylpiperidine derivative, an agricultural and horticultural agent containing the compound as an active ingredient, particularly an agricultural and horticultural insect pest control agent, a tick control agent or a nematode control agent, and a method for using the same.

In the field of agriculture and horticulture, a plant pest control agent for controlling various pests has been developed and put into practical use. However, the emergence of pests or diseases that have acquired drug resistance has become a problem, and the development of new agents has been earnestly desired.
Patent Document 1 describes that a compound group that can include a 1-phenylpiperidine derivative is useful as an insecticide for animals. However, Patent Document 1 discloses a 1-phenylpiperidine derivative having 1 to 3 C _1-6 alkyl groups in a piperidine ring and having a sulfur substituent introduced as a substituent at the 3-position of the phenyl group. Absent. Furthermore, as a result of additional tests on the specific compounds described in Patent Document 1, it was found that their effects on spider mites were insufficient.
Patent Document 2 discloses a substituted phenylpiperazine compound represented by a specific formula. Patent Document 3 discloses a 6-membered C—N-bonded aryl sulfide derivative and an aryl sulfoxide derivative represented by a specific formula. However, none of these compounds disclosed in Patent Documents 2 and 3 has a 1-phenylpiperidine skeleton.

International Publication No. 2006/087162 JP 2015-036377 JP International Publication No. 2015/091267

  In crop production such as agriculture and horticulture, the damage caused by pests and diseases is still great, and development of new agricultural and horticultural agents is desired due to factors such as the occurrence of pests resistant to existing drugs.

As a result of earnest studies to solve the above problems, the present inventors have found that a 1-phenylpiperidine derivative represented by the following formula (1), which is a novel compound not described in the literature, is used as an agricultural and horticultural agent, particularly an agricultural chemical. The present invention has been found to be useful as a horticultural insect pest control agent, mite control agent, nematode control agent or disease control agent, and has completed the present invention.
That is, the present invention relates to the following [1] to [14].

[式中、Rは、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルキニル基、Ｃ_3-6シクロアルキルＣ_1-6アルキル基又はＣ_3-6ハロシクロアルキルＣ_1-6アルキル基を示し、
Xは、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-6シクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6ハロアルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_3-6ハロシクロアルキル基、Ｃ_1-6アルキコキシカルボニル基、Ｃ_1-6ヒドロキシアルキル基、Ｃ_1-6アルコキシＣ_1-6アルキル基、ホルミル基、ハロゲン原子、シアノ基又はニトロ基を示し、
Yは、水素原子、ハロゲン原子、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
Zは、同一であるか又は異なっていても良く、Ｃ_1-6アルキル基を示し、
nは、0又は1の整数を示し、
mは、1〜3の整数を示す]
で表される1-フェニルピペリジン誘導体、そのＮ−オキシド又はその塩。 [1] The following formula (1)

[In the formula, R represents a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group. C _3-6 cycloalkyl C _1-6 alkyl group or C _3-6 halocycloalkyl C _1-6 alkyl group,
X is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkenyl group, C _{2- 6} haloalkynyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _3-6 halocycloalkyl group, C _1-6 alkoxycarbonyl group, C _1-6 hydroxyalkyl group, C _{1- 6} alkoxy C _1-6 alkyl group, formyl group, halogen atom, cyano group or nitro group,
Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
Z may be the same or different and each represents a C _1-6 alkyl group,
n represents an integer of 0 or 1,
m is an integer from 1 to 3]
The 1-phenylpiperidine derivative represented by the formula, its N-oxide or a salt thereof.

[2] The 1-phenylpiperidine derivative according to the above [1], wherein R represents a C _1-6 alkyl group or a C _1-6 haloalkyl group, an N-oxide thereof or a salt thereof.
[3]
X represents a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _1-6 hydroxyalkyl group, a C _1-6 alkoxy C _1-6 alkyl group, a formyl group, a halogen atom or a cyano group, 1] or the 1-phenylpiperidine derivative according to [2], its N-oxide or a salt thereof.
[4]
The 1-phenylpiperidine derivative according to any one of [1] to [3] above, wherein m represents 1, the N-oxide thereof or a salt thereof.

[式中、Rは、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6アルキニル基、Ｃ_3-6ハロアルキニル基、Ｃ_3-6シクロアルキルＣ_1-6アルキル基又はＣ_3-6ハロシクロアルキルＣ_1-6アルキル基を示し、
Xは、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-6シクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6ハロアルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_3-6ハロシクロアルキル基、Ｃ_1-6アルキコキシカルボニル基、Ｃ_1-6ヒドロキシアルキル基、Ｃ_1-6アルコキシＣ_1-6アルキル基、ホルミル基、ハロゲン原子、シアノ基又はニトロ基を示し、
Yは、水素原子、ハロゲン原子、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
Zは、同一であるか又は異なっていても良く、Ｃ_1-6アルキル基を示し、
mは、1〜3の整数を示す]
で表される1-フェニルピペリジン誘導体の製造方法であって、
下式（3）

［式中、X、 Y、 Z及び mは、式（２）で定義した通りであり、halo¹はハロゲン原子を示す］
で表される1-フェニルピペリジン誘導体と、下式（4）

［式中、Rは、式（２）で定義した通りである］
で表されるチオールとを反応させる工程を含む、製造方法。 [5]
The following formula (2)

[In the formula, R represents a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _3-6 haloalkynyl group. C _3-6 cycloalkyl C _1-6 alkyl group or C _3-6 halocycloalkyl C _1-6 alkyl group,
X is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkenyl group, C _{2- 6} haloalkynyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _3-6 halocycloalkyl group, C _1-6 alkoxycarbonyl group, C _1-6 hydroxyalkyl group, C _{1- 6} alkoxy C _1-6 alkyl group, formyl group, halogen atom, cyano group or nitro group,
Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
Z may be the same or different and each represents a C _1-6 alkyl group,
m is an integer from 1 to 3]
A method for producing a 1-phenylpiperidine derivative represented by:
Below formula (3)

[In the formula, X, Y, Z and m are as defined in formula (2), and halo ¹ represents a halogen atom]
1-phenylpiperidine derivative represented by the following formula (4)

[In the formula, R is as defined in the formula (2)]
The manufacturing method containing the process of making it react with the thiol represented by.

[式中、Xは、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-6シクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6ハロアルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_3-6ハロシクロアルキル基、Ｃ_1-6アルキコキシカルボニル基、Ｃ_1-6ヒドロキシアルキル基、Ｃ_1-6アルコキシＣ_1-6アルキル基、ホルミル基、ハロゲン原子、シアノ基又はニトロ基を示し、
Yは、水素原子、ハロゲン原子、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
Zは、同一であるか又は異なっていても良く、Ｃ_1-6アルキル基を示し、
halo¹は、ハロゲン原子を示し、
mは、1〜3の整数を示す]
で表される1-フェニルピペリジン誘導体の製造方法であって
下式（５）

［式中、X、 Y及びhalo¹は、式（３）で定義した通りであり、halo²は、ハロゲン原子を示す］
で表されるベンゼン誘導体と、下式（6）

［式中、Z及びmは、式（３）で定義した通りである。］
で表されるピペリジン誘導体とを反応させる工程を含む、製造方法。 [6]
The following formula (3)

[In the formula, X represents a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkenyl group. , C _2-6 haloalkynyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _3-6 halocycloalkyl group, C _1-6 alkoxycarbonyl group, C _1-6 hydroxyalkyl group , C _1-6 alkoxy C _1-6 alkyl group, formyl group, halogen atom, cyano group or nitro group,
Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
Z may be the same or different and each represents a C _1-6 alkyl group,
halo ¹ represents a halogen atom,
m is an integer from 1 to 3]
A method for producing a 1-phenylpiperidine derivative represented by the following formula (5)

[In the formula, X, Y and halo ¹ are as defined in formula (3), and halo ² represents a halogen atom]
And a benzene derivative represented by the following formula (6)

[In the formula, Z and m are as defined in the formula (3). ]
The manufacturing method containing the process of making it react with the piperidine derivative represented by.

[7]
An agricultural and horticultural chemical comprising the 1-phenylpiperidine derivative according to any one of [1] to [4] above, an N-oxide thereof or a salt thereof.
[8]
An agro-horticultural tick control agent containing the 1-phenylpiperidine derivative according to any one of [1] to [4] above, an N-oxide thereof or a salt thereof.
[9]
A nematode control agent for agricultural and horticultural use, containing the 1-phenylpiperidine derivative according to any one of [1] to [4] above, an N-oxide thereof or a salt thereof.
[10]
An agricultural and horticultural insect pest control agent comprising the 1-phenylpiperidine derivative according to any one of [1] to [4] above, an N-oxide thereof or a salt thereof.
[11]
An agricultural and horticultural disease preventive agent containing the 1-phenylpiperidine derivative according to any one of [1] to [4] above, an N-oxide thereof or a salt thereof.

[12] Controlling pests of plants, comprising a step of treating pests and / or their habitat, and / or plant seeds and / or plant propagation materials with the agricultural and horticultural chemical according to the above [7]. how to.
[13] Preventing plant pests, including a step of treating a place where a useful crop is to be grown, a place where it is growing, or a growing crop with the agricultural and horticultural chemical according to [7] above. how to.
[14] A method for preparing an agrochemical composition, which comprises a step of mixing the agricultural and horticultural chemical according to [7] with a bulking agent and / or a surfactant.

  The compound of the present invention exhibits excellent effects as an agricultural and horticultural agent, particularly an agricultural and horticultural insect pest control agent, a tick control agent, a nematode control agent or a disease control agent. It is also effective against harmful insects that parasitize pets such as dogs and cats, or livestock such as cows and sheep.

In the definition of the compound of the present invention represented by the formula (I), the “halogen atom” is, for example, chlorine atom, bromine atom, iodine atom or fluorine atom. The “C _1-6 alkyl group” is, for example, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a s-butyl group, a t-butyl group, an n-butyl group. A linear or branched alkyl group having 1 to 6 carbon atoms such as a pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, an n-hexyl group and an isohexyl group is shown. “C _1-6 haloalkyl” refers to a linear or branched alkyl group having 1 to 6 carbon atoms, which may be the same or different and is substituted with one or more halogen atoms. The “C _3-6 cycloalkyl” refers to a cyclic cycloalkyl group having 3 to 6 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.

Examples of the C _1-6 haloalkyl group include fluoromethyl group, chloromethyl group, difluoromethyl group, trifluoromethyl group, chlorodifluoromethyl group, bromodifluoromethyl group, dichlorofluoromethyl group, 1-fluoroethyl group, 2 -Fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2-iodoethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 2,2- Difluoroethyl group, 1-fluoroisopropyl group, 3-fluoropropyl group, 3-chloropropyl group, 3-bromopropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 4-fluorobutyl group, 4-chlorobutyl, nonafluorobutyl group Group, etc., preferably substituted with 1 to 9 halogen atoms And straight chain or branched chain haloalkyl groups having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms.

Examples of the C _2-6 alkenyl group include vinyl group, allyl group, isopropenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1,1-dimethyl-2-propenyl group, 1-ethyl-2-propenyl group, 1-methyl-2-butenyl group, 1-methyl-3-butenyl group, 2-hexenyl group, 3- Carbon number having at least one double bond at any position such as hexenyl group, 4-hexenyl group, 5-hexenyl group, 1,1-dimethyl-2-butenyl group, 1,1-dimethyl-3-butenyl group 2-6, Preferably a C2-C4 linear or branched alkenyl group is mentioned.

Examples of the C _2-6 haloalkenyl group include 1-fluorovinyl group, 2-fluorovinyl group, 2,2-difluorovinyl group, 3-chloro-2-propenyl group, 3,3-difluoro-2-allyl group. Group, 3,3-dichloro-2-allyl group, 4,4,4-trifluoro-2-butenyl group, 4,4,4-trifluoro-3-butenyl group, 5-chloro-3-pentenyl group, A 6-fluoro-2-hexenyl group or the like, which has at least one double bond at any position and is preferably substituted with 1 to 9 halogen atoms, has 2 to 6 carbon atoms, and preferably has 2 to 4 carbon atoms. A chain or branched chain haloalkenyl group may be mentioned.

Examples of the C _2-6 alkynyl group include ethynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-butynyl group, 2-butynyl group and 3 -Butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 1-methyl-3-butynyl group, 1,1-dimethyl-2- C2-C6 having at least one triple bond at any position such as a butynyl group, a 1,1-dimethyl-3-butynyl group, a 1-methyl-3-pentynyl group, a 1-methyl-4-pentynyl group, Preferred is a linear or branched alkynyl group having 2 to 4 carbon atoms.

As the C _2-6 haloalkynyl group, a fluoroethynyl group, 4,4,4-trifluoro-2-butynyl group, 5,5,5-trifluoro-3-pentynyl group, 1-methyl-3,3, 3-trifluoro-2-butynyl group, 1-methyl-5,5,5-trifluoro-2-pentynyl group or the like having at least one triple bond at any position, preferably 1-9 halogen atoms A substituted linear or branched haloalkynyl group having 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms can be mentioned.

Examples of the C _1-6 alkoxy group include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, cyclopropyloxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, n-pentoxy group. , N-hexyloxy groups and the like, and straight-chain or branched-chain alkoxy groups having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms.

Examples of the C _1-6 haloalkoxy group include a fluoromethoxy group, dichloromethoxy group, trichloromethoxy group, difluoromethoxy group, trifluoromethoxy group, chlorodifluoromethoxy group, bromodifluoromethoxy group, dichlorofluoromethoxy group, 1- Fluoroethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 2-iodoethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, penta Fluoroethoxy group, 1-fluoroisopropoxy group, 3-fluoropropoxy group, 3-chloropropoxy group, 3-bromopropoxy group, 4-fluorobutoxy group, 4-chlorobutoxy group and the like, preferably 1-9 1 to 6 carbon atoms, preferably carbon, substituted with a halogen atom The linear or branched haloalkoxy groups of the formulas 1 to 3 can be mentioned.

Examples of the C _3-6 halocycloalkyl group include 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl and 1-chlorocyclo. Propyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 2,2-dibromocyclopropyl, 1-fluorocyclobutyl, 2-fluorocyclobutyl, 3 -Fluorocyclobutyl, 3,3-difluorocyclobutyl, 3,3-dichlorocyclobutyl, 1-fluorocyclopentyl, 2-fluorocyclopentyl, 3-fluorocyclopentyl, 2,2-difluorocyclopentyl, 3,3-difluorocyclopentyl 2 , 2-dichlorocyclopentyl, 1-f Examples thereof include a halocycloalkyl group having 3 to 6 carbon atoms, which is preferably substituted with 1 to 9 halogen atoms, such as a luorocyclohexyl group.

Examples of the C _3-6 cycloalkyl C _1-6 alkyl group include cyclopropylmethyl, 2-cyclopropylethyl, 3-cyclopropylpropyl, 4-cyclopropylbutyl, 5-cyclopropylpentyl, 6-cyclopropylhexyl. And groups such as cyclobutylmethyl and cyclopentylmethyl.

Examples of the C _3-6 halocycloalkyl C _1-6 alkyl group include 1-fluorocyclopropylmethyl, 2-fluorocyclopropylmethyl, 2,2-difluorocyclopropylmethyl, 2-chlorocyclopropylmethyl, 2, 2-dichlorocyclopropylmethyl, 2- (2,2-difluorocyclopropyl) ethyl, 2- (2,2-dichlorocyclopropyl) ethyl, 3- (2,2-difluorocyclopropyl) propyl, 4- (2 , 2-difluorocyclopropyl) butyl, 5- (2,2-dichlorocyclopropyl) pentyl, 6- (2,2-difluorocyclopropyl) hexyl, 2,2-difluorocyclobutylmethyl, 2,2-dichlorocyclo Butylmethyl, 3,3-difluorocyclopentylmethyl, 3,3-dichlorocyclopentyl Methyl, 4,4-difluoro-cyclohexyl methyl or 4,4-dichloro cyclohexyl methyl and the like.

Examples of the C _1-6 alkoxycarbonyl group include groups such as methoxycarbonyl, ethoxycarbonyl, n-propylcarbonyl, n-butylcarbonyl, n-pentylcarbonyl, n-hexylcarbonyl and i-propylcarbonyl groups.

Examples of the C _1-6 hydroxyalkyl group include groups such as hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl and 3-hydroxypropyl.

Examples of the C _1-6 alkoxy C _1-6 alkyl group include methoxymethyl, ethoxymethyl, 1-propyloxymethyl, 2-propyloxymethyl, methoxyethyl, ethoxyethyl, 1-propyloxyethyl, 2-propyloxy. Examples thereof include groups such as ethyl.

Examples of the salt of the 1-phenylpiperidine derivative represented by the above formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate, acetate, fumarate, maleate, Examples thereof include organic acid salts such as oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate and the like.
The 1-phenylpiperidine derivative represented by the above formula (1) of the present invention may have one or more asymmetric centers in its structural formula, and may have two or more optical isomers and diastereomers. May exist, and the present invention includes all optical isomers and mixtures containing them in arbitrary ratios. Further, the 1-phenylpiperidine derivative represented by the above formula (1) of the present invention may have two geometric isomers derived from a carbon-carbon double bond in the structural formula, The invention also includes all geometric isomers and mixtures containing them in arbitrary proportions.

Among the compounds of the present invention, compounds in which R represents a C _1-6 alkyl group, a C _1-6 haloalkyl group or a C _3-8 cycloalkyl group are preferred, and further, a C _1-6 alkyl group, a C _1-6 Compounds showing a haloalkyl group are particularly preferred.
Among the compounds of the present invention, compounds in which X represents a C _1-6 alkyl group, a C _1-6 hydroxyalkyl group, a C _1-6 alkoxy C _1-6 alkyl group, a formyl group cyano group or a halogen group are preferable, and further, Is particularly preferably a compound showing a C _1-6 alkyl group, a C _1-6 hydroxyalkyl group, a C _1-6 alkoxy C _1-6 alkyl group, a formyl group or a cyano group.
Among the compounds of the present invention, a compound in which Y represents a hydrogen atom, a halogen group or a C _1-6 alkyl group is preferable, and a compound in which Y represents a halogen group or a C _1-6 alkyl group is particularly preferable.
Among the compounds of the present invention, a compound in which Z represents a C _1-6 alkyl group is preferable, and a compound in which Z represents a C _1-3 alkyl group is particularly preferable.
Among the compounds of the present invention, compounds in which m is an integer of 1 or 2 are preferable, and compounds in which m is 1 are particularly preferable.

  Hereinafter, a representative method for producing the novel 1-phenylpiperidine derivative represented by the formula (1) of the present invention and the intermediate 1-phenylpiperidine derivative represented by the formula (3) will be shown. The present invention is not limited to these.

[式中、XはＣ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-6シクロアルキル基、Ｃ_2-6アルケニル基、Ｃ_2-6アルキニル基、Ｃ_2-6ハロアルケニル基、Ｃ_2-6ハロアルキニル基、Ｃ_1-6アルコキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_3-6ハロシクロアルキル基、Ｃ_1-6アルキコキシカルボニル基、Ｃ_1-6ヒドロキシアルキル基、Ｃ_1-6アルコキシＣ_1-6アルキル基、ホルミル基、ハロゲン原子、シアノ基又はニトロ基を示し、
Yは水素原子、ハロゲン原子、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
Zは、同一であるか又は異なっていても良く、Ｃ_1-6アルキル基を示し、
halo¹及びhalo²はそれぞれ独立にハロゲン原子を示し、
mは、1〜3の整数を示す。] Reaction formula 1

[In the formula, X is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkenyl group, C _2-6 haloalkynyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _3-6 halocycloalkyl group, C _1-6 alkoxycarbonyl group, C _1-6 hydroxyalkyl group, C _1-6 alkoxy represents a C _1-6 alkyl group, a formyl group, a halogen atom, a cyano group or a nitro group,
Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
Z may be the same or different and each represents a C _1-6 alkyl group,
halo ¹ and halo ² each independently represent a halogen atom,
m represents an integer of 1 to 3. ]

  In the method shown in Reaction Scheme 1, the 1-phenylpiperidine derivative represented by the above formula (3) is obtained by converting the phenyl compound represented by the above formula (5) and the piperidine compound represented by the above formula (6) into a base. It is produced by reacting in the presence or absence of an inert solvent.

  As the solvent used in the reaction between the compound of formula (5) and the compound of formula (6), a solvent inert to the reaction can be widely used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene, halogenated methylene chloride, 1,2-dichloroethane, chloroform, etc. Hydrocarbon solvents, ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ester solvents such as methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, amides such as N, N-dimethylformamide. Examples thereof include system solvents, nitrile solvents such as acetonitrile and propionitrile, and aprotic polar solvents such as N-methylpyrrolidone and N, N′-dimethylimidazolinone. These solvents can be used alone or in a mixture of two or more as necessary.

As the base used in the reaction between the compound of formula (5) and the compound of formula (6), known inorganic bases and organic bases can be used. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate and sodium bicarbonate, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal hydrogen such as sodium hydride and potassium hydride. And the like. Examples of the organic base include alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide, amines such as triethylamine and pyridine. These bases may be used alone or in combination of two or more.
Such a base can be used in an amount of usually 1 to 100 equivalents, preferably 1 to 2 equivalents relative to the phenyl compound represented by the above formula (5).

The ratio of the phenyl compound represented by the formula (5) to the piperidine compound represented by the formula (6) is more preferably 1 to 2 moles of (6) per 1 mole of (5). .
The reaction can be carried out usually within the range of −78 ° C. to the boiling temperature of the solvent used, and the reaction is preferably carried out at room temperature to 100 ° C.
Although the reaction time varies depending on the reaction temperature and the like and cannot be generally stated, the reaction is usually completed in about 0.5 to 24 hours.

  The target compound obtained in each reaction can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like, Further, it can be purified by a conventional purification means.

［式中、X, Y, Z, R, halo¹, mは前記で定義した通りである。］ Reaction formula 2

[In the formula, X, Y, Z, R, halo ¹ , and m are as defined above. ]

  In the method shown in Reaction Scheme 2, the 1-phenylpiperidine derivative represented by the above formula (2) comprises a 1-phenylpiperidine compound represented by the above formula (3) and a thiol compound represented by the above formula (4). , In the presence or absence of a base, in an inert solvent.

  As the solvent used in the reaction between the 1-phenylpiperidine derivative of the above formula (3) and the thiol compound of the above formula (4), widely known solvents may be used as long as they are inert to the reaction. You can For example, alcohols such as methanol, ethanol, n-propanol and iso-propanol, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane and heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene and xylene. Solvents, halogenated hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane and chloroform, ether solvents such as diethyl ether, tetrahydrofuran and 1,4-dioxane, ester solvents such as methyl acetate and ethyl acetate, N, Examples thereof include amide solvents such as N-dimethylformamide, and solvents such as N-methylpyrrolidone, N, N′-dimethylimidazolinone and acetonitrile. These solvents can be used alone or in a mixture of two or more as necessary.

As the base used in the reaction between the compound of formula (3) and the compound of formula (4), known inorganic bases and organic bases can be used. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate and sodium bicarbonate, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal hydrogen such as sodium hydride and potassium hydride. And the like. Examples of the organic base include alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide, amines such as triethylamine and pyridine. These bases may be used alone or in combination of two or more.
Such a base can be used in an amount of usually 1 to 100 equivalents, preferably 1 to 2 equivalents relative to the phenyl compound represented by the above formula (5).

The 1-phenylpiperidine derivative of the formula (3) and the thiol compound represented by the formula (4) can be appropriately used in a wide range. It is preferably used in an amount of 1 to 5 mol or more, and more preferably 1.0 to 2.0 mol.
The reaction is preferably carried out at room temperature to the boiling temperature of the solvent used, and more preferably at room temperature to under heating under reflux.
The reaction time is usually 0.5 to 24 hours, and the reaction is completed.

  After completion of the reaction, it may be isolated from the reaction system containing the desired product by a conventional method, and if necessary, the desired product can be produced by purification by recrystallization, column chromatography or the like. Further, it is also possible to use the product of interest in the next reaction step without isolating it from the reaction system.

［式中、X、Y、R、Z、mは前記で定義した通りである。］
反応式３に示す方法においては、前記式（７）で表される1-フェニルピペリジン誘導体が、前記式（２）で表される1-フェニルピペリジン誘導体の酸化反応により製造される。 Reaction formula 3

[In the formula, X, Y, R, Z and m are as defined above. ]
In the method shown in Reaction Scheme 3, the 1-phenylpiperidine derivative represented by the above formula (7) is produced by the oxidation reaction of the 1-phenylpiperidine derivative represented by the above formula (2).

  As the solvent used in the oxidation reaction of the 1-phenylpiperidine compound represented by the formula (2), a solvent inert to the reaction can be widely used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene, halogenated methylene chloride, 1,2-dichloroethane, chloroform, etc. Hydrocarbon solvents, alcohol solvents such as methanol and ethanol, ester solvents such as methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, amide solvents such as N, N-dimethylformamide, acetonitrile and propio Examples thereof include nitrile solvents such as nitrile, aprotic polar solvents such as N-methylpyrrolidone, N, N′-dimethylimidazolinone, and acetic acid. These solvents can be used alone or in a mixture of two or more as necessary.

Examples of the oxidant used in the oxidation reaction of the 1-phenylpiperidine compound represented by the formula (2) include m-chloroperbenzoic acid, sodium periodate, hydrogen peroxide, tert-butyl hypochlorite, Sodium hypochlorite and the like can be mentioned.
Such an oxidizing agent can be used in an amount of usually 1 to 3 equivalents, preferably 1 to 2.5 equivalents, relative to the 1-phenylpiperidine derivative represented by the formula (1-0).

The reaction can be carried out usually in the range of −78 ° C. to the boiling temperature of the solvent used, and it is preferable to carry out the reaction at 0 ° C. to room temperature.
Although the reaction time varies depending on the reaction temperature and the like and cannot be generally stated, the reaction is usually completed in about 0.5 to 24 hours.
The target compound obtained in each reaction can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method, or the like, Further, it can be purified by a conventional purification means.

Representative compounds of the 1-phenylpiperidine derivative represented by the formula (1) are shown in Table 1, and representative compounds of the 1-phenylpiperidine derivative represented by the formula (3) are shown in Table 2. However, the present invention is not limited to these.
In addition, the physical properties in the table indicate properties and melting point (° C.), “n-” is normal, “s-” is secondary, “t-” is tertiary, and “i-” is “Me” represents a methyl group, “Et” represents an ethyl group, “Pr” represents a propyl group, “Bu” represents a butyl group, and “Ph” represents a phenyl group.

General formula (1)

table 1

Table 2

  The compounds of the present invention can be used for the prevention and control of harmful organisms in situations such as agriculture, indoors, forests, livestock and hygiene. The specific use situations, target pests and use methods are shown below, but the contents of the present invention are not limited to these.

  The compound of the present invention represented by the formula (1) is an agricultural crop, for example, an edible crop (rice, barley, wheat, rye, oats, or other wheat, corn, potato, sweet potato, taro, soybean, red bean, broad bean, Peas, beans, beans such as peanuts, etc.), vegetables (cabbage, Chinese cabbage, radish, turnip, broccoli, cauliflower, cruciferous crops such as komatsuna, pumpkin, cucumber, watermelon, snow cucumber, melon etc. , Eggplant, tomato, pepper, pepper, okra, spinach, lettuce, lotus root, carrot, burdock, garlic, onions such as onion, onion, etc., mushrooms (shiitake, mushrooms, etc.), fruit trees and fruits (apple, citrus) , Pears, grapes, peaches, plums, cherry, walnuts, chestnuts, almonds, bananas, strawberries, etc., fragrances and other crops for appreciation (lavender, rosemary, thyme) Parsley, pepper, ginger, etc., special crops (cigarette, tea, sugar beet, sugar cane, hops, cotton, hemp, olive, rubber, coffee, etc.), grass and feed crops (timothy, clover, alfalfa, corn, sorghum) , Orchardgrass, grasses, legumes, etc.), turf (Koryo turf, bentgrass, etc.), forest trees (Todomatsu, Ezomatsu, pine, hiba, cedar, cypress, etc.) and ornamental plants (Kiku, rose) , Carnations, herbs and flowers such as orchids, garden trees such as ginkgo, sakura, Aoki, etc.), arthropods, molluscs, nematodes, and fungal phylum, phylum Mycobacterium, bacteria phyla, It can also be used to control fungi such as Actinomyces and pests such as bacteria.

As a specific pest,
Lepidoptera, an insect of the arthropod family Lepidoptera, for example, Helicoverpa armigera, Heliothis spp., Agrotis segetum, Autographa nigrisigna, Trichoplusia ni , Spodoptera exigua, Spodoptera exigua, Spodoptera litura, etc., diamondback moth (Plutella xylostella), etc. ), Midarekamonmonamaki (Archips fuscocupreanus), Chahamaki (Homona magnanima), Chanohosoga (Caloptilia theivora), Nasihimesinkui (Grapholita molesta), etc. ), Momohamoguriga (Lyonetia clerkella), etc. Phyllocnistis citrella of the moth family, Phylllonorycter ringoniella of the Hosogae family, etc., Leek-of-mouth moth (Acrolepiopsis sapporensis) of the Atomhycoga family, etc. , Pectinophora gossypiella, etc. of the family Mothidae, peach mosquito (Carposina niponensis), etc. of the family Squid, etc. Chilo suppressalis, Scirpophaga incertulas, Cobnomeiga (Cnaphalocrocis medinalis), Himalulan moga (Hellulla ungooga, Condalcus, etc.) es punctiferlis), cotton helicopter moth (Diaphania indica), grasshopper moth (Parapediasia teterrella), etc. Etc., Pieris rapae crucivora, etc. Phalaera flavescens, Malacosoma neustrium testaceum, Saturnia japonica, etc., Euproctis pseudoconspersa, Orygia recens approximans, etc. Mulberry Li (Spilosoma imparilis), such as the United States white Arctiidae (Hyphantria cunea), Grape berry moth (Endopiza viteana), codling moth (Laspeyresia pomonella) adults such as, larvae and eggs;

Coleoptera For example, the chafer beetle (Anomala cuprea), the beetle (Popillia japonica), the coral beetle (Oxycetonia jucunda), the chafer beetle (Anomala geniculata), etc. Melonotus fortnumi of the click beetle family, etc., Epilachna vigintioctopunctata of the ladybug family, etc. femoralis, rootworm species (Diabrotica spp.), Phyllotreta striolata, beetle beetle (Cassida nebulosa), beetle beetle (Phaedon brassicae), rice beetle (Oulema oryzae), Mexican beetle ham (Epilachna variis). tinotarsa decemlineata, etc., Rhynchites heros from the family Olepididae, Rhynchites heros, etc., Cylas formicarius from the family Weevil Weevil, etc. Anthonomus gradis grandis), weevil weevil (Sphenophrus venatus vestitus) and other adults, larvae and eggs such as Epuraea domina of the poppy family;
Heteroptera of the order Hemiptera For example, the stink bug (Eurydema rugosum), the long-tailed stink bug (Eysarcoris lewisi), the stinkweed stink bug (Eysarcoris parvus), the minamiula ara viper (Plautia stali), stag beetle (Halymorpha mista), etc., Urochela luteovoria, etc. Cretus punctiger, etc., Limpocorisa chinensis, etc., Dysdeercus cingulatus, etc., stephanitis nashi, etc. , Aphididae (Apolygus sp.) inolai), red scabbard beetle (Stenotus rubrovittalus), red beard (Trigonotylus coelestialium), etc.

Homoptera of the order Hemiptera. For example, Platypleura kaempferi in the family Cicidae. White-necked leafhopper (Nephotettix virescens), etc. (Diaphorina citri) and other whiteflies of the whitefly family (Aleurocanthus spiniferus), silverleaf whiteflies (Bemisia argentifolii), various types of Bemisia tabaci (Bemisia tabaci) biotypes, whiteflies (Dialeurodes citri), whiteflies whitefly des vaporariorum) etc., grape aphid (Viteus vitifolii) etc. of Aphidaceae, etc. Aphids (Brevicoryne brassicae), Citrus aphids (Toxoptera aurantii), Citrus aphids (Toxoptera citricidus), Aphis chinensis (Aulacorthum magnoliae), Prunus aphis (Schizaphis piricola), Prunus aphis (Napimidae polkoni), Napumi aphid (Niphora aphis piricola) Lipaphis erysimi), peach aphid (Hyalopterus pruni), stag beetle (Pleotrichophorus chrysanthemi), aphid (Macrosiphoniella sanborni), broad beetle (Megoura crassicauda) Aphid (Sitobion ibarae), Tulip aphid (Macrosiphum euphorbiae), Aphis gossypii (Myzus varians), Green peach aphid (Myzus persicae), Red peach aphid (Rhopalosiphum rufiabdominalis), Barbet beetle (Wheat beetle) Aphids (Sitobion akebiae), apple beetles (Eriosoma lanigerum), etc., Icerya purchasi, etc. in the family Pseudococcidae, etc. (Phenacoccus kraunhiae), etc., such as the scale insect beetle (Ceroplastes ceriferus), the ruby beetle (Ceroplastes rubens), etc., and the scale bug (Aonidiella aurantii), the pest scale (Comstockaspis perniciosa). White peach scale (Pseudaulacaspis pentagoa), Unaspis yanonensis (Unaspis yanonensis) adults, such as, larvae and eggs;

Thysanoptera For example, the Thrips thrips (Thirps ini) (Thrips tabi) (Thrips tabi) (Thrips seta), Thrips seta, Thrips setosus, Thrips setosus Thrips (Frankliniella occidentalis), croton thrips (Heliothrips haemorrhoidalis), etc.
Hymenoptera For example, Athalia rosae ruficornis of the wasp family, Arge pagana, etc., Apple wasp of the Aphididae family, Arge mali, etc. Adult larvae such as leafcutter wasps (Megachile nipponica nipponica) and larvae of the ant family (Formica japonica); egg;
Flies (Diptera) For example, soybean gall midge (Asphondylia yushimai), etc., fruit fly (Rhacochlaena japonica), fruit fly (Bactrocera cucurbitae), etc. Drosophila suzukii, etc., such as Limomyza trifolii, tomato leaf fly (Liriomyza sativae), peach fly (Chromatomyia horticola), rice leaf fly (Agromyza oryzae), leaf fly (Agromyza oryzae), L. (Delia platura), adults such as onion fly (Delia antiqua), larvae and eggs;
Orthoptera For example, Locusta migratoria in the grasshopper family, Ruspolia lineosa in the grasshopper family, etc. Etc. Adults, larvae and eggs of the grasshopper family Oxya yezoensis;
Termites (Isoptera) For example, adults such as the termite (Odontotermes formosanus) of the termite family, larvae and eggs;
Adults, larvae and eggs of the order Dermaptera, such as, for example, the giant bollworm (Labidura riparia) of the Coccinellidae;

Adults, larvae and eggs of Collembola of the phylum Arthropoda (Collembola), for example, Sminthurus viridis, etc.
Adults, larvae and eggs such as Isopada of the arthropod molluscs, for example, the pill bug (Armadillidium vulgare), etc.
Acari of the arthropod spider (Acari), for example, Polyphagotarsonemus latus of the dust mite family, Phytonemus pallidus, etc. ), Minami Himebatani (Brevipalpus phoenicis), etc. ununguis), Bryobia eharai, Eotetranychus kankitus, Clover spider mites, such as Bryobia praetiosa, Aculus Schlechtendali) , Fake Rust mite (Eriophyes chibaensis), tulip rust mite (Aceria tulipae), grape dwarf mite (Colomerus vitis), peach rust mite (Aculus fockeui), green mite (Calacarus carinatus), etc. Adults, larvae and eggs;

Archaenioglossa of the molluscs gastropods (Architaenioglossa), for example, Pomacea canaliculata of the family Spodoptera, Plumonata, for example, Achatina fulica of the African snail family, slugs of the slug family. Meghimatium bilineatum), the slug family (Milax gagates), the slug family (Lehmannina valentiana), the white-tailed snail family (Acusta despecta sieboldiana), etc .;

Tylenchida of the linear phylum Pteridophyceae, for example, Ditylenchus destructor of the Anguinaceae family, Namishukuschutoni of the Tyrenkorinkusu family, Tylenchorhynchus claytoni, etc. , Heterodermaceae (Pratylenchus coffeae), etc., Hopilolymaceae (Helicotylenchus dihystera), etc., Heterodera, potato cyst nematode (Globodera rostochiensis), etc. (Criconema jaejuense) etc., Strawberry Messenchu of the Anguina family (Nothotylenchus acris), etc., Strawberry Nematode of the Aferencoides family (Aphelecchoides fragarriae), etc .;
Doririmus of the coccygeal gland, for example, Longidleidae (Xiphinema sp.), Trichodolacean Yumiharisenchu (Trichodorus sp.);

Examples include fungi and bacteria such as fungi (Eumycota), morphomycetes (Myxomycota), bacteria (Bacteriomycota), actinomyces (Actinomycota) and the like.

  The diseases to which the compound of the present invention represented by the formula (1) can be applied include, specifically, rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), and blight (Rhizoctonia solani). ), Endogenous brown disease (Pantoea ananatis), Brown streak (Acidovorax avene subsp. Avenae), Leaf sheath brown disease (Pseudomonas fuscovaginae), White leaf blight (Xanthomonas oryzae pv. Oryzae), Burkholderia plantarii, etc. ; Powdery mildew of wheat (Erysiphe graminis), Fusarium head blight (Gibberella zeae), Leaf rust (Puccinia striiformis, P. graminis, P. recondita, P. hordei), Snow rot (Typhula sp., Micronectriella nivalis) , Nautilus scab (Ustilago tritici, U. nuda), Tangle scab (Tilletia caries), Eyespot (Pseudocercosporella herpotrichoides), Cloud rot (Rhynchosporium secalis), Leaf blight (Septoria tritici), Blight (Leptosphaeria nodorum) ), Reticulopathic disease (Pyrenophora teres), Hyomon's disease (Helminthosporium zonatum Ikata), and black-blight (Pseudo) monas syringae pv. japonica) etc .; citrus sunspot (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum), brown rot (Phytophthora citrophthora, P. nicotianae), Black scab (Phyllosticta citricarpa), etc .; Monilinia mali (Apple), rot (Valsa mali), powdery mildew (Podosphaera leucotricha), leaf spot (Alternaria mali), scab (Venturia inaequalis), scab (spot) Mycospherella pomi), anthracnose (Colletotrichum acutatum), ring spot (Botryosphaeria berengeriana), scab (Gymnosporangium yamadae), scab (Monilinia fructicola), etc .; without scab (Venturia nashicola, V. pirina), black Spot disease (Alternaria kikuchiana), red scab (Gymnosporangium haraeanum), ash scab (Monilinia fructigena), etc .; tangerine scab (Monilinia fructicola), black scab (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.) Disease (Brenneria nigrifluens), etc .; grape black wilt (E lsinoe ampelina), late rot (Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black lotus (Guignardia bidwellii), downy mildew (Plasmopara viticola), and brown scab (Monilinia fructigena) , Scab (Cladosporium viticolum), gray mold (Botrytis cinerea), bacterial root blight (Agrobacterium vitis), etc .; oyster anthracnose (Gloeosporium kaki), leaf scab (Cercospora kaki, Mycoshaerella nawae), etc .; Anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea, Oidiopsis taurica), vine blight (Didymella bryoniae), split vine (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), plague (Phythra) .), Seedling blight (Pythium sp.) And the like; cucumber spot bacterial disease (Pseudomonas syringae pv. Lochrymans), marginal bacterial disease (Pseudomonas viridiflava), brown spot bacterial disease (Xanthomonas campestris pv. Cucurbitae), etc .; melon Xanthomonas campestris pv. Cucurb itae), hairy root disease (Agrobacterium rhizogens), cancerous disease (Streptomyces sp.) and the like; watermelon fruit blotch bacterial disease (Acidovorax avenae pv. citrulli) and the like; eggplant blight (Ralstonia solanacearum) and the like; Tomato ring spot (Alternaria solani), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans), scab (Clavibacter michiganense subsp. Michiganense), stem scab (Pseudomonas corrugata), soft rot (Pectobacterium carotovorum subsp.) carotovorum) etc .; brown leaf blight (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum) etc .; black spot (Alternaria japonica), white spot (Cercosporella brassicae) soft rot (Pectobacterium carotovorum subsp. carotovorum) of cruciferous vegetables Etc .; cabbage rot (Pseudomonas syringae pv. Marginalis), black rot (Xanthomonas campestris pv. Campestris), etc .; lettuce rot (Pseudomonas cichorii, Pseudomonas viridiflava), bacterial spot (Xanthomonas campestr) is pv. vitians) Green onion rust (Puccinia allii), etc .; Soybean purpura (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), etc. Colletotrichum lindemthianum), etc .; black scab (Cercospora personata), brown spot (Cercospora arachidicola), etc .; powdery mildew (Erysiphe pisi), etc .; summer blight of potatoes (Alternaria solani), plague (Phytophthora) infestans), leaf rot fungus (Rhizoctonia solani), etc .; strawberry powdery mildew (Sphaerotheca humuli), etc .; tea net blast (Exobasidium reticulatum), white scab (Elsinoe leucospila), red blight (Pseudomonas syringae pv. theae) , Canker disease (Xanthomonas campestris pv. Theicola), etc .; tobacco scab (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), plague (Phytophthora nicotianae). , Ralstonia solanacearum, sky Disease (Pectobacterium carotovorum subsp. Carotovorum), etc .; brown spot of sugar beet (Cercospora beticola), seedling blight (Aphanomyces cochliodes), etc .; rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), etc. Brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana), root gall (Agrobacterium tumefaciens), etc .; Gray mold (Botrytis cinerea), sclerotium of various crops such as eggplant, cucumber and lettuce Disease (Sclerotinia sclerotiorum); snow rot of turf (Pythium iwayamai, Tyohula incarnate, Fusarium nivale, Sclerotinia borealis), powdery mildew (Erysiphe graminis), farrying disease (Lycoperdon perlatum, Lepista subnudo, Marasmius, Marasmius) Rot (Ceratobasidium spp.), Wilt (Gaemannomyces graminis), curvularia leaf blight (Curvularia geniculata), leaf rot (Rhizoctonia solani), psyllium disease (Pythium periplocum, Pythium vanterpoolii), rust (P uccinia spp.), dollar spot disease (Sclerotinia homoeocarpa), etc .; red grass disease (Pythium aphanidermatum) of bentgrass, and anthracnose (Colletotrichum sp.).

The compound of the present invention represented by the above formula (1) is active indoors in buildings including general houses, and damages or decomposes wood and its processed products such as wooden furniture, stored food, clothing, books, etc. However, it can also be used to control arthropods and fungi that damage our lives. As a specific pest,
Termites of the arthropod family Insecta, for example, the termites Coptotermes formosanus, Reticulitermes speratus, and other termites of the genus Reticulitermes hesperus, R. tibialis, R. flavipes, R. lucifugus, R. santonensis, etc.), American termites (Incisitermes minor), termites (Odontotermes formosanus), termites (Hodotermopsis jzponica), adult larvae (Cryptotermes domesticus) and larvae of the termites (Cryptotermes domesticus). ;

Coleoptera, for example, weevil (Sitophilus zeamais) of the family Weevil weevils, Sitophilus zeamais, etc. Tribenium castaneum, Tribolium confusum, etc., Saw beetle, Oryzaephilus surinamensis, Cryptolestes pusillus, etc. Stegobium paniceum), etc., such as Attagenus unicolor japonicus, Anthrenus verbasci, Dermestes maculatus, etc. Adults such as the giant leopard beetle (Gibbium aequinnoctiale), the long-tailed beetle (Dinoderus minutus), the long-tailed beetle (Rhizopertha dominica), and the larvae (Lyctus brunneus), etc.

Lepidoptera For example, Cudra cautella of the family Moga family (Ephestia kuehniella), Plodia interpunctella (Plodia interpunctella), etc. ), Adult larvae such as carp (Tineola bisselliella), larvae and eggs;
Caterpillars For example, adults, larvae, and eggs of Licocelidae (Lepinotus reticulatus), etc., and Hiposachateta (Liposcelis bostrychophilus), etc.
Cockroaches For example, Blattella germanica of the German cockroach family, Blattella germanica, adult cockroaches (Periplaneta fuliginosa), adult cockroaches (Periplaneta japonica), larvae and eggs;

Hymenoptera, for example, adults, larvae, and eggs of the family Ants (Monomorium pharaoni), ants (Monomorium nipponense), and the like;
Lamiforms, for example, adult larvae and eggs such as Ctenolepisma villosa and Lepisma saccharina of the family Lamiaceae;
Flies, for example, adults, larvae and eggs of Drosophila melangogaster etc. of the family Drosophilidae, cheese flies (Piophila casei) of the family Cheesefly, etc .;

Mites of the arthropod spider, for example, adults such as Tyrophagus putrescentiae of the mites, Lardoglyphus konoi, etc., carpoglyphus lactis, etc., larvae and eggs;

Tyromyces palustris, Coriolus versicolor, etc., which are wood-rotting fungi of fungi;
Aspergillus niger, Aspergillus terreus, Aureobasidium pullulans, Chaetomium globosum, Cladosporium cladosporioides, Eurotium tonophilus, Fusarium moniliforme, Gliocladium virens, Myrothecium verrucarillium, Penicillium citricum, Penicillen citricium, Penicillium citricium, Penicillium citric acid, and Penicillium citric acid.

The compound of the present invention represented by the formula (1) can also be used for controlling pests that damage or weaken trees in natural forests, artificial forests and urban green areas. As a specific pest,
Lepidoptera of the arthropod Insecta, for example, Spodoptera, Calliteara argentata, Euphortis pseudoconspersa, Orygia recens approximans, Euproctis subflava, Lymantria dispar, etc. Malacosoma neustria testacea, Matsukareha (Dendrolimus spectabilis), Tsuendakareha (Dendrolimus superans), Crytoblabes loxiella, etc. Ptycholoma lecheana circumclusana), Clymiga (Cydia kurokoi), Cydia cryptomeriae, etc. Hiro Helia Monema flavescens (Parasa lepida), Himekuroiraga (Scopelodes contracus), Tenguiraga (Microleon longipalpis) adults, such as, larvae and eggs;

Coleoptera For example, Anomala rufocuprea from the family Scarabaeidae, Heptophylla picea, etc., Aphilus spinipennis from the family Buprestidae, etc. pallidula) and other weevil weevil (Scepticus griseus) and pine weevil (Shirahoshizo insidiosus) and other weevil (Sipalinus gigas), etc. ) Etc., adults such as Rhizopertha dominica, etc., larvae and eggs;

Stink bugs For example, Cinara todocola of the aphid family, Aedes japonicus of the family Aphididae, Adelges japonicus, etc. ) Such as adults, larvae and eggs;
Hymenoptera: For example, Pachynematus itoi of the wasp family, etc., honey bee (Neodiprion sertifer) of the wasp family, etc.
Flies, for example, Tipula aino from the family Gamagidae, Strobilomyia laricicola from the family Ganoderidae, Contarinia inouyei from the family Ganodermae, Contarinia matsusintome ;

Mites of the arthropod spider, for example, adults, larvae, and eggs such as Oligonichus hondoensis and Oligonichus ununguis;
Linear animal genus Pteridophyceae Tyrenx, for example, the pine wood nematode (Bursaphelenchus xylophilus) of the Parasitaferenx family.

  The compound of the present invention represented by the above formula (1) is internally used in vertebrates, particularly warm-blooded vertebrates such as cattle, sheep, goats, horses, pigs, poultry, dogs, cats, fish, and other domestic animals and pets. Alternatively, it can also be used for the prevention / treatment or control of arthropods, nematodes, trematodes, tapeworms, and protozoa that parasitize externally. In addition to the above, the target animal species also include rodents such as mice, rats, hamsters and squirrels, carnivores such as ferrets, and avian pets such as ducks and pigeons and experimental animals.

As a specific pest,
The fly of the arthropod Insecta, for example, Yamato flies (Tabanus rufidens), Tabanus chrysurus, etc. of the Musciidae, Musca bezzii of the housefly, Musca domestica, Stomoxys calcitrans, etc. Family fly (Gasterophilus intestinalis), etc., bull fly (Hypoderma bovis), etc., sheep fly (Oestrus ovis), etc. , Culex pipiens molestus, Culex pipiens, Culex pipiens, Culex pipiens, Culex pipiens molestus, Culex pipiens molestus Anopheles sinensis, Culex pipiens triaeni orhynchus summorosus), Aedes albopictus, etc., etc., belonging to the family Gnatidae (Simulium iwatense), Prociulium yezoense, etc .;
Flea order For example, adults, larvae and eggs of cat fleas (Pulex irritans), canine fleas (Ctenocephalides canis), etc .;

Lice: For example, porcelain lice (Haematopinidae suis) and bovine lice (Haematopinidae eurysternus), etc. Adults such as Menopon gallinae), larvae and eggs;
Mites of the arthropod spider For example, honeybees of the family Acaridae (Varroa jacobsoni), ticks of the tick (Haemaphysalis longicornis), ticks of the tick (Ixodes ovatus), ticks of the tick (Boophilus microplus), ticks of the hawk idiom naruma (Aramida). ), Etc., Ornithonyssus sylvialum, etc., Dermanyssus gallinae, etc., Demodex phylloides, etc. Knemidocoptes mutans) and other adults, larvae and eggs such as Otodectes cynotis, and Psoroptes communis.

C. elegans of the phylum Lepidoptera, for example, Beetle hookworm, porcine nematode, porcine lungworm, ciliary nematode, tuberculosis tuberculosis, etc .:
Roundworm, for example, roundworm, roundworm, etc .;
Ptozoa ascidian, for example, Schistosoma japonicum, liver tetsu, deer fluke, paragonimus westermani, chick fluke of Japanese egg, etc .;
Tapeworms, for example, leaf tapeworms, dilated tapeworms, tapeworms of Beneden, tapeworms of the quadrilateral, tapeworms of the ditch groove, tapeworms of the ringed ring, etc .:
Protozoa, such as Histomonas, etc., of the class Pteroflagellate, Proflagellates, such as Leishmania, Trypanosoma, etc., Polychaetes, such as Giardia, etc.
Amoeba of the fleshy class, eg Entamoeba;
Pyroplasma subclasses of the genus Sporozoa, such as Theilaria and Babesia, and subclasses of the late sporozoa, such as Eimeria, Plasmodium and Toxoplasma, can be mentioned.

  The compound of the present invention represented by the above formula (1) is for exterminating pests which directly cause harm or discomfort to the human body, or for maintaining a public health condition against pests carrying or transmitting pathogens. Can also be used for

As a specific pest,
Lepidoptera of the arthropod Insecta, for example, Sphrageidus similis of the family Spodoptera, Kunugia undans of the family Karegaga, etc .; Adults, larvae and eggs of;
Coleoptera: For example, Xanthochroa waterhousei of the family Scorpionidae, etc., Epimeta gorhani of the family Asteraceae, etc., and adults and larvae of Paederus fuscipes;
Vespa For example, adults such as Vespa simillima xanthoptera of the wasp family, etc., Brachyponera chinensis of the ant family, etc., larvae and eggs of Batozonellus annulatus of the family Vespidae, etc .;

Flies, for example, the mosquito family Armigeres subalbatus, etc., the sika family Culicoides nipponensis, etc., the chironomid family Chironomus yoshimatsui, etc., the gnat family Simulium nikkoense, etc. , Etc., Musca domestica, etc. of the Musca domestica, Fannia canicularis of the Musca domestica, etc., Phromia regina of the Musca domestica, etc., Sarcophaga peregrina of the flesh family, etc. , Larvae and eggs;
Flea order For example, adults such as human flea (Pulex irritans), larvae and eggs of the family Flea;
Cockroaches For example, Blattella germanica of the German cockroach family, etc., adult cockroaches (Periplaneta americana) of the cockroach family, Periplaneta fuliginosa, adult larvae of the cockroach (Periplaneta japonica), larvae and eggs;
Orthoptera, for example, adults, larvae and eggs of the family Corogidae, such as Diestrammena japonica and Diestrammena apicalis;
Liceae For example, adults such as head lice (Pediculus humanus humanus) and the like, lice (Phthirius pubis), larvae and eggs;
Stink bugs For example, adults, larvae and eggs of the white-backed tortoise (Isyndus obscurus) such as the bed bug (Cimex lectularius) of the bed bug, etc .;

Adults, larvae and eggs, such as Collembola of the phylum Insecta of the arthropod phyla (Hypogastrura communis).
For example, Ixodes persulcatus of the tick family, Ornithonyssus bacoti, etc., Chelacaropsis moorei, etc. ), Etc., Demodex folliculorum, etc., Dermotophagoides pteronyssinus, etc., Chimite mites, Sarcoptes scabiei, etc .;
Authentic arachnids, for example, Chiracanthium japonicum from the family Araneidae, Heteropoda venatoria from the family Aceridae, Spermophora senoculata from the family Spidermothae spp. Etc. Adults, larvae and eggs of the jumping spider, Plexippus paykulli, and Missi flycatcher (Plexippus adansoni);
Scorpions, for example, adults, larvae and eggs such as Isometrus europaeus of the family Scorpionaceae;
Thalassinidae of the arthropod Lepidoptera, for example, adults, larvae and eggs of Scolopendra subspinipes mutilans and Acolmdra (Scolopendra subspinipes japonica);
Gedoptera, for example, adults, larvae, and eggs such as Geddies (Thereuronema hilgendofi) of the family Gedaceae;
Adults, larvae and eggs such as Oxidus gracilis of the family Polyptera, for example.
Isopods of the arthropod Crustacea, for example, adult larvae such as Porcellio scaber, larvae and eggs;
Annelids of the annelid Lepidoptera, for example, Yamavir (Haemadipsa zeylanica japonica) of the family Yamavir;

Trichophyton rubrum, Trichophyton mentagrophytes, etc., Trichophyton mentagrophytes, Candida albicans, etc., Candida albicans, Aspergillus fumigatus, etc., Escherichia coli, Pseudomonas aeruginosa, Gram-negative bacteria, Staphylococcus aureus Staphylococcus Gram-positive bacteria such as aureus can be mentioned.

  The compound of the present invention represented by the formula (1) is a pest that damages trees and ornamental plants in agricultural crops, natural forests, artificial forests and urban green areas, such as arthropods, gastropods, nematodes, Of particular value in controlling fungi. In such a situation, the compounds of the invention may be incorporated into other active compounds such as insecticides, acaricides, nematicides, fungicides in their commercially useful formulations and in the use forms prepared by those formulations. It can also be present as a mixture with agents, synergists, plant regulators, poison baits or herbicides.

  Usable forms include wettable powders, wettable powders, dry flowables, aqueous solutions, emulsions, liquids, oils, flowables such as water suspensions / emulsions, capsules, powders, granules and fine powders. Granules, baits, tablets, sprays, fumes, aerosols and the like can be taken. In order to obtain these dosage forms, various agricultural chemical adjuvants conventionally used in the technical field of agricultural and horticultural chemicals can be appropriately used. Such pesticide adjuvants can be used for the purpose of, for example, improving the effect of agricultural chemicals and horticultural chemicals, stabilizing them, and improving dispersibility. Examples of pesticide adjuvants include carriers (diluents), spreading agents, emulsifiers, wetting agents, dispersing agents, disintegrating agents, and the like. As the liquid carrier, water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethylsulfoxide, and methyl. Examples thereof include naphthalene, cyclohexane, animal and vegetable oils and fatty acids. As the solid carrier, clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, gum arabic and the like can be used. As the emulsifier and the dispersant, an ordinary surfactant can be used, and examples thereof include higher alcohol sodium sulfate, stearyl trimethyl ammonium chloride, polyoxyethylene alkylphenyl ether, anionic surfactants such as lauryl betaine. , Cationic surfactants, nonionic surfactants, amphoteric surfactants and the like can be used. Further, a spreading agent; a wetting agent such as dialkylsulfosuccinate; a fixing agent such as carboxymethyl cellulose or polyvinyl alcohol; a disintegrating agent such as sodium ligninsulfonate and sodium lauryl sulfate can be used. Of course, the compound of the present invention may be used alone or in combination of two or more, and may be blended as an active ingredient. The content of the compound of the present invention as an active ingredient in these formulations is, for example, 0.01 to 99.5% by mass, preferably selected from the range of 0.5 to 90% by mass, formulation form, application method, etc. Although it may be appropriately determined according to various conditions, for example, about 0.5 to 20% by mass, preferably about 1 to 10% by mass for powders, and about 1 to 90% by mass for wettable powders, preferably 10%. It can be prepared so as to contain the active ingredient in an amount of about 80 to 80% by weight, or about 1 to 90% by weight, and preferably 10 to 40% by weight, in an emulsion.

  In order to control arthropods, gastropods, nematodes, and fungi, the foliage of the plant should normally be located at the place where damage is caused by these pests or the place where damage may occur. In addition to spraying to soil, all layers of soil are mixed, row application, mixing of floor soil, cell seedling treatment, planting hole treatment, plant treatment, top dress, rice box treatment, water surface application, etc. It can also be used after being absorbed from. Further, it can also be used by soaking seeds in a drug, seed treatment such as seed dressing, calper treatment, application to a nutrient solution in a nutrient solution (hydroponic) cultivation, smoke or trunk injection. When used, it varies depending on the type and amount of pests generated and the type and cultivation form and growth state of the target crop / tree, but generally 0.1-1000 g, preferably 1-100 g per 10 ares of active ingredient. Apply. To treat this, wettable powder, granule wettable powder, dry flowable agent, water solvent, emulsion, liquid agent, flowable agent such as water-suspending agent / water-emulsion agent, and capsule are diluted with water, Although it varies depending on the type, cultivation form and growth state of the target plant, in general, it may be applied to crops at an application rate of 10 to 1000 liters per 10 ares. In addition, powders, sprays or aerosols may be applied to crops and the like in the state of their formulations.

  When the target pest mainly harms plants in soil or when the drug is absorbed from the root part to control the target pest, for example, the formulation is diluted with water or not diluted. To the plant base or nursery for raising seedlings, the method of spraying granules to the plant base or nursery for raising seedlings, powder, wettable powder, granule water before sowing or transplanting A method of spraying a disinfectant, granules, etc. and mixing with the whole soil, a planting hole before sowing or before planting a plant, a powder, a wettable powder, a wettable powder, a granular wettable powder, a granular wettable powder, etc. And the like. Wettable powders, wettable powders, water-soluble solvents, emulsions, solutions, flowable agents such as suspensions / emulsions in water, capsules, etc. are diluted with water, and generally 5 to 500 liters per 10 ares. Then, it may be sprayed on the soil surface or irrigated into the soil so that it is even over the entire area to be treated.For powders, granules, fine granules or baits, etc. So that it can be sprayed on the soil surface. Spraying or irrigation may be done around the seed or crop / tree that you want to protect from harm. In addition, the active ingredient can be mechanically dispersed by cultivating during or after the application.

  As a method of applying paddy rice to a nursery box, the dosage form may differ depending on the application time such as application at the time of sowing, application at the greening period, application at the time of transplantation, and for example, powder, granule wettable powder, granule, fine powder It may be applied in a dosage form such as granules. It can also be applied by admixing with soil, such as admixture of soil with powder, powder wettable powder, granules or fine granules, for example, bed soil admixture, cover soil admixture, admixture to the entire soil. it can. Alternatively, the soil and various preparations may be applied alternately in layers.

  As a method for applying to paddy fields, solid preparations such as jumbo preparations, pack preparations, granules and wettable granules, and liquid preparations such as flowables and emulsions are usually applied to flooded paddy fields. In addition, at the time of rice planting, an appropriate formulation can be sprayed or injected into the soil as it is or by mixing it with fertilizer or the like. Further, by using a chemical solution such as emulsion or flowable as a source of water flowing into a paddy field such as a water spout or an irrigation device, it can be applied labor-savingly as water is supplied.

  Examples of the seed treatment method include a method of diluting a liquid or solid preparation and dipping the seed in a liquid state without dilution to allow the drug to adhere and penetrate, and a solid preparation or a liquid preparation mixed with the seed. Examples of the methods include a method of applying a dressing treatment to adhere to the surface of the seed, a method of mixing with an adhesive carrier such as a resin or a polymer to coat the seed, and a method of spraying near the seed at the same time as planting. The "seed" for performing the seed treatment means a plant in the early stage of cultivation used for the propagation of plants, for example, seeds, bulbs, tubers, seed potatoes, plant buds, baskets, bulbs or nutrients for cuttings cultivation. The plant for breeding can be mentioned. Further, the "soil" or "cultivation carrier" of the plant when applied is a support for cultivating a crop, particularly a support for growing roots, the material is not particularly limited, the plant is So long as it can grow, it may be so-called soil, seedling mat, water, etc. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel substances, polymer substances, rocks. Examples thereof include wool, glass wool, wood chips and bark.

  As the sowing of the cultivated plants to be transplanted and the treatment at the seedling raising stage, in addition to direct treatment of seeds, irrigation treatment of liquid chemicals or spray treatment of granules to seedbeds for raising seedlings is preferable. In addition, it is also preferable to treat the planting holes with granules at the time of planting, or to mix the granules with a cultivation carrier in the vicinity of the transplanting place.

The compound of the present invention represented by the above formula (1) protects wood (standing trees, fallen trees, processed wood, stored wood or structural wood) from damage by insects such as termites or nematodes and fungi. Is also worth it. In such a situation, it is possible to control the wood or the soil around it by spraying / injecting / irrigating / applying oil, emulsion, wettable powder, sol, spraying powder, granules, etc. it can. In addition, the oils, emulsions, wettable powders, powders, etc. used in the present situation are mixed with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists. The total amount of the active ingredient compounds in these preparations is 0.0001 to 95% by weight, preferably 0.005 to 10% by weight in oils, powders and granules, emulsions, wettable powders and sol preparations. Can be contained at 0.01 to 50% by weight. When controlling arthropods, fungi, etc., spray 0.01 to 100 g of active ingredient compound per m ² on soil or wood surface.

  The compound of the present invention represented by the above formula (1) is used when a product such as cereals, fruits, tree nuts, spices and tobacco is stored as it is, powdered or mixed in the product. It can be used to protect from the damage of eyes, Coleoptera, mites and fungi. Also, when storing animal products (skin, wool, wool, feathers, etc.) and plant products (cotton, paper, etc.) in their natural or converted state, they are protected from attack of Lepidoptera, Coleoptera, Spots and cockroaches. It can be protected and can be protected from attacks of Lepidoptera, Coleoptera, flies and mites when storing foods such as meat and fish. In such situations, methods such as spraying oils, emulsions, wettable powders, powders, etc., installing resin vaporizers, treating smoke agents and fumes, installing granules, tablets and poison baits, spraying aerosols, etc. Can be controlled with. These formulations can also be present as a mixture with other active compounds, such as insecticides, acaricides, nematicides, fungicides, repellents or synergists, in these formulations. May contain the active ingredient compound in a total amount of 0.0001 to 95% by weight.

  The compound of the present invention represented by the above formula (1) is a disease of humans and livestock, which is parasitic on the body surface of humans and livestock and causes direct harm such as skin feeding or blood feeding. Worth controlling or preventing arthropods, nematodes, trematodes, tapeworms, protozoa, and arthropods that cause human discomfort, which are the vectors of such diseases. There is. In such a situation, the compound of the present invention may be mixed in a small amount of food or feed, or a suitable orally ingestible pharmaceutical composition such as tablets, pills containing a pharmaceutically acceptable carrier or coating substance, Oral administration as a capsule, paste, gel, beverage, medicated feed, medicated drinking water, medicated feed, sustained-release large pills, other sustained-release devices such as those retained in the gastrointestinal tract, or spray, powder, It can be transdermally administered as grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo and the like. In order to achieve the effect in such applications, the formulation generally contains 0.0001 to 0.1% by weight, preferably 0.001 to 0.01% by weight of the active ingredient compound. As a method for transdermal administration or topical administration, a device (for example, a collar, a medallion or an ear tag) attached to an animal so as to locally or systemically control the arthropod can be used.

  Specific oral administration methods and transdermal administration methods when the compound of the present invention represented by the above formula (1) is used as an anthelmintic agent for animals such as livestock and pets or humans are shown, but not limited thereto. Not something.

  When administered orally as a medicated water, the beverage is usually a suspension, dispersion or dispersion in a suitable non-toxic solvent or water with suspending or wetting agents such as bentonite or other excipients. is there. Beverages also generally contain an antifoaming agent. Beverage formulations generally contain 0.01 to 1.0% by weight of active ingredient compound, preferably 0.01 to 0.1% by weight.

  When it is desirable to administer orally in a dry individual unit dosage form, capsules, pills or tablets containing a predetermined amount of the active ingredient are usually used. These use forms are obtained by homogeneously mixing the active ingredient with appropriately milled diluents, fillers, disintegrants and / or binders such as starch, lactose, talc, magnesium stearate, vegetable gums and the like. Manufactured. Such unit dosage formulations can vary widely in weight and content of anthelmintic agents depending on the type of host animal being treated, the degree of infection and the type of parasite and the body weight of the host.

  When administered by animal feed, it can be dispersed homogeneously in the feed, used as a top dressing or used in the form of pellets. Usually, to achieve the desired antiparasitic effect, the final feed contains 0.0001-0.05% by weight, preferably 0.0005-0.01% by weight, of the active ingredient compound.

  Those dissolved or dispersed in a liquid carrier excipient can be parenterally administered to animals by intragastric, intramuscular, intratracheal or subcutaneous injection. For parenteral administration, the active compounds are preferably mixed with suitable vegetable oils such as peanut oil, cottonseed oil. Such a formulation generally contains 0.05 to 50% by weight, preferably 0.1 to 5.0% by weight, of the active ingredient compound. It can also be administered topically by mixing with a suitable carrier such as dimethyl sulfoxide or a hydrocarbon solvent. This formulation is applied directly to the external surface of the animal by spraying or direct pouring.

  In addition, the compound of the present invention represented by the above formula (1) is a potential insecticide for arthropods which are directly harmful or arthropods which are vectors of diseases, and their pests are latent. For the surrounding environment, spraying, injecting, irrigating and applying oils, emulsions, wettable powders, spraying powders, fumigants, mosquito coils, self-burning fumes, chemical reaction fumes Heat fumes such as, fog and other smoke agents, treatment of ULV agents, installation of granules, tablets and poison baits, or waterways such as floating powders and granules, wells, reservoirs, water tanks and other running water or suspended water It can also be used by a method such as dropwise addition to. Furthermore, it is possible to control, in the same manner as the above-mentioned method, against damselfish, which is also an agricultural and forest pest, and to fly, etc., by mixing in livestock feed and mixing with feces. It is also effective to use mosquitoes, etc., and volatilize them into the air with an electric mosquito trap. It should be noted that the preparations which are in the form of use thereof can also be present as a mixture with other active compounds such as pest control agents, tick control agents, nematode control agents, disease control agents, repellents or synergists. The total amount of the active ingredient compounds contained in these preparations is 0.0001 to 95% by weight.

The compounds of the invention of the formula (1) can also be present as admixtures with other active compounds. Especially for the control of pests such as arthropods, gastropods and nematodes which damage plants when used in combination with a compound (insecticide) having pest control activity, mite control activity or nematode control activity. On the other hand, the pests to be controlled can be expanded, and synergistic effects such as reduction of the dose can be expected. As its specific active compound,
Organic phosphorus agents such as acephate, azinphos-methyl, chlorpyrifos, diazinon, dichlorvos, dimeton-S-methyl, dimethoate, dimethyl Vinphos, dimethylvinphos, disulfoton, ethion, fenitrothion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, monocrotophos. ), Naled, naled, oxydeprophos, parathion, phensoate, phenthoate, phosalone, pirimiphos-methyl, pyridafenthion, profenof os), prothiofos, propaphos, pyraclofos, salicion, sallithion, sulprofos, thiometon, tetrachlorvinphos, tetrachlorvinfos, trichlorphon, vamidothion. etc;
Carbamate agents, for example, alanycarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, and fratiocarb. furathiocarb), isoprocarb (isoprocarb), methomil (methomyl), metolcarb (metolcarb), pirimicarb (proprim), propoxur (propoxur), thiodicarb (thiodicarb);

Organochlorine agents such as aldrin, chlordane, DDT (p, p'-DDT), endosulfan, lindane, etc .;
Pyrethroids such as acrinathrin, allethrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cyhalothrin, cyphenothrin, cypermethrin, deltamethrin ), Etofenprox, fenpropathrin, fenvalerate, fluvaltriate, flucythrinate, flufenprox, fluvalinate, furamethrin, halofenprox (Halfenprox), imiprothrin (imiprothrin) permethrin, phenothrin, phenothrin, prallethrin, pyrethrins, resmethrin, silafluofe (Silafluofen), tefluthrin (tefluthrin), tralomethrin (tralomethrin), transfluthrin (transfluthrin), etc;
Neonicotinoid agents such as acetamiprid, clothianidin, dinotefran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, etc .;
Diamide agents, for example, chlorantraniliprore, cyantraniliprore, cyclaniliprore, flubenziamid, etc .;
Phenylpyrazole agents such as ethiprole, fipronil, acetoprole, pyrafluoprole, pyriplore and the like;

Nereistoxin agents, such as bensultap, cartap, thiocyclam, thiosultap, etc .;
Insect growth regulators such as phenylbenzoylurea agents and diacylhydrazines, such as chlorofluazuron, diflubenzuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novallon. novaluron), teflubenzuron, triflumuron, buprofezin, chromafenozide, halofenozide, methoxyphenozide, tebufenozide, cilomadine, cyromazine.
Juvenile hormone agents, such as diofenolan, phenoxycarb, hydroprene, methoprene, pyriproxyfen and the like;

Insecticidal substances produced by microorganisms such as abamectin, emamectin-benzoate, ivermectin, lepimectin, milbemectin, nemadectin, nemadectin, nikkomycin, Polyoxin complex (polioxin), spinetoram (spinetram), spinosad (spinosad), BT agent, etc .;
Insecticidal substances derived from natural products such as anabasine, azadiractin, deguelin, fatty acid glyceride (decanolyoctanoylglycerol), hydroxypropyl starch, soybean lecithin, nicotine , Nornicotine, oreic acid sodium salt, machine oil (petroleum oil), propylene glycol monolaurate, rapeseed oil, rape oil, rotenone, sorbitan fatty acid ester (Sorbitan) fatty acid ester), starch, etc .;

Other insecticides include, for example, afidpyropen, chlorfenapyr, diafenthiuron, DBEDC (Dodecylbenzenesulphonic acidbisethylenediamine copper [II] salt), flonicamid (flometoquin), flufenerim (flufenerim). , Flupyradifurone, hydramethylnon, hydramethylnon, indoxacarb, metaflumizone, metaflumizone, metaaldehyde, nicotin sulfate, pymetrozine, pyridalyl, pyrifluquinazone. pyrifluquinqzon), spiro tetramat (spirotetramat), sulfoxaflor (sulfoxaflor), tolfenpyrad (tolfenpyrad), triazamate (triazamate), etc .;

Acaricide, for example, acequinocyl, amidoflumet, amitraz, azocyclotin, benzoximate, bifenazate, binapacryl, phenisobromolate, quinomethionate. (Chinomethionat), clofentezine (clofentezine), cienopyrafen (cyenopyrafen), cyflumetofen (cyflumetofen), tricyclohexyltin hydroxide (cyhexatin), dicofol (dicofol), dienochlor (dienochlor), etoxazole (ethoxazole), fenazaflor (fenazaflor), Fenazaquin, fenbutatin oxide, phenothiocarb, fenpyroximate, fluacrypyrim, hexythiaz ox), pirimidifen, polynactins, propargite, propflubumide, pyflubumide, pyridaben, spirodiclofen, spirodiclofen, spiromesifen, tebufenpyrad, tetradiphone (Tetradifon) etc .;

Nematicides, for example, aluminum phosphide, benclothiaz, benclothiaz, cadusafos, etoprophos, fluensulfone, fosthiazate, furfural, imiciafos, imicyafos, Levamisol hydrochloride, mesulfenfos, metam-ammonium, methyl isothiocyanate, moranteltartarate, oxamyl, thioxazafen, etc .;

Examples of poison bait include chlorphacinone, coumatetralyl, diphacinone, monofluoracetate, sodium fluoracetate, and warfarin.

  The compound of the present invention represented by the above formula (1) may be present as a mixture with an active compound other than the compound having pest control activity, mite control activity or nematode control activity. In order to control diseases and / or weeds that occur simultaneously at the time of use, by using a mixture with a compound having bactericidal activity, herbicidal activity or plant growth regulating activity, it is possible to reduce the control effort and the dosage, etc. Synergistic effects can be expected. In addition, when used in combination with a repellent or synergist, a more effective control effect such as a synergistic effect can be expected.

As the specific active compound, a disease controlling agent, for example,
DD (1,3-dichloropropene), acibenzolar-S-methyl, aldimorph, ametoctradin, amisulbrom, andisoprim, andoprim, triazine, azaconazole , Azoxystrobin, basic copper sulfate, benodanil, benomyl, benthiavalicarb-isopropyl, benhiazole, bitertanol , Bixafen, blasticidin S, boscalid, bromuconazole, calcium carbonate, buthiobate, lime-sulfur mixture, calcium polysulfide, captafor captafol), captan, captan Bendazole (carbendazim), carboxin (carboxin), carpropamid (carpropamid), quinomethionate (chinomethionat), chlorfenazole (chlorfenazole), chloroneb (chloroneb) chloropicrin, chlorothalonil (chlorothalonil), chlorzolinate (chlozolinate), DBEDC of bis (ethylenediamine) copper-bis- (dodecylbenzenesulfonic acid)), cupric hydroxide, copper nonylphenol sulfonate, basic copper chloride, cyazofamid, cyfluphenamide (Cyflufenamid), cimoxanil, cyproconazole, cyprodinil, cyprodinil, dazomet, diclobutrazol, diclobutrazol, diclofluanid, dichlone, diclolone Met (diclocymet), diclomezine (diclomezine), diethofencarb (diethofencarb), difenoconazole (difenoconazole), diflumetrim (diflumetorim), dimethomorph (dimethostrobin) (dimoxystrobin), diniconazole (diniconazole), dinicoazole , Dithane-stainless, dithianon, dodine, echlomezole, edifenphos, enestrobin, epoxiconazole, etaconazole, etaboxam. ethaboxam), shiitake mushroom mycelium extract (extract from mushroom), famoxadone (famoxadone), fenamidone (fenamidone), fenarimol (fenarimol), fenbuconazole (fenbuconazole), fenfuran (fenfuram), Fenhexamid, fenoxanol, fenpiclonil, fenpropidin, fenproprazin, fenpyrazamine, ferimzone, fluazinam, flumetover, flumorphover, flumorph , Fluopicolide, fluopyram, fluoroimide,
Fluotrimazole, fluoxastrobin, fluquinconazole, flusulfamide, flutolanil, fluxapyroxad, folpet, fosetyl aluminum (fosetyl) -AL), futhalide, fuberidazole, fludioxonil, flusilazole, flusilazole, flutianil, flutriafol, furametpyr, fluconazole, guazatine , Hexaconazole, hydroxyisoxazole, hydroxymexazol, hymexazol, imazalil, imazalil sulfate, imibenconazole, imibenconazole Minoctadine acetate, iminoctadine-DBS, ipconazole, IBP, iprobenfos, iprodione, iprovalicarb, iprovalicarb, isofetamid, isoprothiolane, isoprothiolane, isoprothiolane, isoprothiolane, isoprothiolane (Isopyrazam), isotianil, kasugamycin, kresoxim-methyl, mancozeb, mandipropamid, manneb, manzeb, mepanipyrim, mepanipyrim. mepronil), metalaxyl, carbam (metam-ammonium), carbam sodium (metam-sodium), metconazole, metasulfocarb (methasulfocarb), methyl bromide, methyl isothiocyanate Anate (methylisothiocyanate), metominostrobin (metominostrobin), metrafenone (metrafenone), mildiomycin (mildiomycin), microbutanil (myclobutanil), organic sulfur nickel salt (nickel dimethyldithiocarbamate), nuarimol (nuarimol), orysastrobin (orysastrobin), oxazyl oxadixyl), oxathiapiprolin, organic copper (oxine-copper), oxolinic acid, oxpoconazole fumarate, oxycarboxin, oxytetracycline , Pebulate, pefurazoate, penconazole, pencycuron, penflufen, penthiopyrad, picarbutrazox, pico Cistrobin, piperalin, polycarbamate, polyoxin-B, polyoxins, potassium hydrogen carbonate, probenazole, prochloraz, prochloraz, Procymidone, propamocarb, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin, pyramethostrobin, pyramethostrobin Strobin (pyraoxystrobin), pyrazophos (pyrazophos), pyribencarb (pyribencarb), pyridinitril (pyridinitril), pyrifenox (pyrifenox), pyrimethanil (pyrimethanil), pyriophenone (pyriofenone),
Pyroquilon, quinoxyfen, quintozene, sedaxane, silver, simeconazole, sodium hydrogen carbonate, sodium hypochlorite, spiroxamine (Spiroxamine), streptomycin, sulfur, tebfloquin, tebuconazole, tecloftalam, terbinafine, terbinafine, tetraconazole, thiabendazole, thiadiazine, thiadiazine. , Thifluzamide, thiophanate, thiophanate, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolprocarcar b), tolylfluanid, triadimefon, triadimenol, triadimenol, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole (Triflumizole), triforine (triforine), triticonazole (triticonazole), uniconazole P (uniconazole-P), validamycin (validamycin (-A)), vinclozolin (zalilamide), zinc sulfate (zinc sulfate) , Zineb, ziram, zoxamide and the like.

Examples of compounds having herbicidal activity include aclonifen, acifluofen-sodium, alachlor, alloxydim, amicarbazone, amidesulfuron, anilofos. , Asulam, atrazine, azimsulfuron, azimsulfuron, benfuresate, bensulfuron-methyl, bentazone, benthiocarb, benzobicyclon, benzofe Benzofenap, bialaphos, bifenox, bromobutide, bromoxynil, butamifos, cafenstrol, calcium peroxide, carbetamibe (Carbetamide), cinosulfuron, cromeprop, cyclosulfamuron, cyclosulfamuron, cyhalofop-butyl, daimuron, desmedipham, diclofop- methyl), diflufenican, dimefuron, dimethametryn, dimethametryn, dinoterb, diquat, diuron, esprocarb, esprocarb, ethiozin, ethofumesate, ethofumes, ethofumes. Ruflon (ethoxysulfuron), etobenzanid, fenoxaprop-P-ethyl, fentrazamide, flucarbazone, flufenacet, flutamon, flurtamone, furchiaset Methyl (fluthiacet-methyl), foramsulfuron (foramsulfuron), glufosinate-ammonium, glyphosate-isopropyl amine, glyphosate-trimesium, imazapir (imazopyrfuron), imazosulfur ), Indanofan, indosulfuron, iodosufluron, ioxynil-octanoate, isoproturon, isoxadifen, isoxaflutole, lactofen, linuron, mefenacet. (Mefenacet), mesosulfuron (metosulfuron), metamitron (metamitron), metabenzthiazuron (methabenzthiazuron), metosulam (metosulam), metribuzin (metribuzin), napropamide (napropamide), nebulon (neburon) Oxadiargyl, oxadiazon, oxaziclomefone, paraquat, pendimethalin, pentoxazone, phenmedipham, phenmedipham, pretilachlor, propoxycarbazone, propoxycarbazone , Prosulfocarb, pyraclonil, pyraflufen-ethyl, pyraflufe n-ethyl, pyrazolate, pyrazosulfuron-ethyl, pyributicarb, pyriftalid, Pyriminobac-methyl, quizalofop-ethyl, setoxidim, simazine, sulcotrion, sulfentrazone, tenilchlor nylchlor), triaziflam, tribufos and the like can be exemplified.

Further, as a compound having a plant growth regulating action, for example,
1-naphthylacetamide (1-naphthylacetic acid), 4-CPA (4-CPA), benzylaminopurine (6-benzylaminopurine), butoralin (butralin), calcium chloride (calcium chloride), calcium formate (calcium formate), peroxide Calcium peroxide, calcium sulfate, chlormequat chloride, choline, cyanamide, cyclanilide, daminozide, decyl alcohol, dichlorprop. dichjoprop), ethephon, ethychlozate, flurprimidol, forclorfenuron, gibberellic acid, indolebutyric acid, maleic acid hydrazide potassium (maleic hydrdede). salt), mefenpill (mef) enpyr), mepiquat chloride, oxine sulfate, 8-hydroxyquinoline sulfate, paclobutrazol, paraffin, prohexadione-calcium, pro It can also be used in a mixture with prohydrojasmon, thidiazuron, trinexapac, trinexapac, uniconazole-P, wax and the like.
Repellents, such as capsaicin, carane-3,4-diol, citronellal, deet, dimethyl phthalate, hinokitiol, limonene. , Linalool, menthol, menthone, naphthalene, thiram, etc .;
Synergists such as methylenedioxynaphthalene, naphthyl propynyl ether, naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentynyl phthalimide. ), Phenyl salioxon, piperonyl butoxide, safrole, sesamex, sesamin, sulfoxide, triphenyl phosphate, verbutin, etc. Can be mentioned.

  The compound of the present invention is used as a biopesticide, for example, Cytoplasmic polyhedrosis virus (CPV), insect pox virus (Entomopox virus, EPV), granulosis virus (Granulosis virus, GV), nuclear polyhedrosis virus (Nuclear polyhedrosis). Virus, NPV) and other virus preparations, Beauveria bassiana, Beauveria brongniartii, Monoacrosporium phymatophagum, Paecilomyces fumosorosea pene Trans pasteia Insect killing or killing of Steinernema carpocapsae, Steinernema glaseri, Steinernema kushidai, Verticillium lecanii, etc. Microbial pesticides used as a medicine, Agrobacterium radiobactor, Bacillus subtilis, non-pathogenic Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02, Pseudomonas fluorescens, Talaromyces, Trichoderma atroviride, Trichoderma lignorum used as Trichoderma lignorum The same effect can be expected by mixing with a microbial pesticide, a biological pesticide used as a herbicide such as Xanthomonas campestris, and the like.

  Furthermore, as biological pesticides, for example, Amblyseius californicus, Amblyseius cucumeris, degenerant Amblyseius degenerans, Aphidius colemani, Aphidoletes aphidimyza Chrysoperia carnea), Dwarf beetle (Dacnusa sibirica), Dicklyphus isaea, Encarsia formosa, Eretmocerus eremicus) Black-spotted wasp (Hemiptarsenus varicornis), Red-spotted wasp (Neochrysocharis formosa), Long-spotted stink bug (Orius sauteri), White-spotted stink bug (Orius strigicollis), Chilean dust mite (Phytoseiulus persimilis) Natural enemies such as black gourd turtles (Pilophorus typicus) and giant beetles (Piocoris varius), codrelure (codlelure), cuelure (geraniol), geraniol, jyptor (gyptol), librure (loop), loop lure (loopl) It is also possible to use in combination with pheromone agents such as eugenol (methyl eugenol), orifluure (orfralure), peachflure (peachflure), phycilure (pycilalure), and turpentine (turpentine).

  Hereinafter, the present invention will be described in more detail with reference to Examples, Formulation Examples and Test Examples, but the scope of the present invention is not limited to these Examples, Formulation Examples and Test Examples.

Example 1. Synthesis of 2,5-difluoro-4- (4-methylpiperidin-1-yl) benzonitrile (Compound number: B-1)
4-Methylpiperidine (1.43 g) and potassium carbonate (2.34 g) were added to a solution of 2,4,5-trifluorobenzonitrile (2.07 g) in N, N-dimethylformamide (15 ml). The reaction mixture was stirred at room temperature for 1.5 hours, water (45 ml) and ethyl acetate (45 ml) were added, the organic layer was separated, and the organic layer was washed with water. After drying the organic layer with MgSO ₄ , the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane: EtOAc = 4: 1 / Rf = 0.50) to give 2,5-difluoro-4- (4-methylpiperidin-1-yl) benzonitrile at 2.93 g (oil). Got with.

1-2: 5-Fluoro-2-propylthio-4- (4-methylpiperidin-1-yl) benzonitrile (Compound number: A-1)
A solution of 2,5-difluoro-4- (4-methylpiperidin-1-yl) benzonitrile (B-1) (0.91 g) synthesized in Example 1 in N, N-dimethylformamide (12 ml) was added with sodium 1-. Propanethiolate (0.66g) was added. The reaction solution was stirred at room temperature for 1.5 hours, water (45 ml) and ethyl acetate (45 ml) were added, the organic layer was separated, and the organic layer was washed with water. After drying the organic layer with MgSO ₄ , the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane: EtOAc = 8: 1 / Rf = 0.60) to give 5-fluoro-2-propylthio-4- (4-methylpiperidin-1-yl) benzonitrile (0.69 g ( oil).

1-3: Synthesis of 5-fluoro-2- (propylsulfinyl) -4- (4-methylpiperidin-1-yl) benzonitrile (Compound No. A-2) 5-Fluoro-2 synthesized in 1-2 -Propylthio-4- (4-methylpiperidin-1-yl) benzonitrile (A-1) (0.69 g) was dissolved in chloroform (17 ml) and 70% m-chloroperbenzoic acid (0.76 g) was added at room temperature. The reaction mixture was added and stirred at room temperature for 1 hour. The reaction solution was stirred at room temperature for 1 hour, saturated multistory water (40 ml) and chloroform (10 ml) were added, the organic layer was separated, and then the organic layer was washed with water. After drying the organic layer with MgSO ₄ , the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane: EtOAc = 4: 1 / Rf = 0.20) to give 5-fluoro-2- (propylsulfinyl) -4- (4-methylpiperidin-1-yl) benzonitrile. Obtained with 0.23 g (oil).

The ¹ H-NMR data of the compounds produced in the same manner as in the above Examples are shown in Table 3 below.

Table 3

  Formulations containing the compound of the present invention will be specifically described below with reference to some formulation examples, but the compounds of the present invention, auxiliary components and their addition amounts are of course limited to the following formulation examples. is not. In the formulation examples, all parts are parts by weight.

Formulation Example 1 Emulsion Compound of the present invention (10 parts), xylene (60 parts), N-methyl-2-pyrrolidone (20 parts), Sorpol 3005X (mixture of nonionic surfactant and anionic surfactant, Toho) Chemical Industry Co., Ltd. (trade name) (10 parts) was uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 2 Wettable powder-1
Compound of the present invention (20 parts), Nipseal NS-K (white carbon, Tosoh Silica Co., Ltd., trade name) (10 parts), Kaolin clay (Kaolinite, Takehara Chemical Industry Co., Ltd., trade name) (60 parts) , Sunextract P-252 (sodium lignin sulfonate, Nippon Paper Chemical Co., Ltd., trade name) (5 parts) and Lunox P-65L (alkylallyl sulfonate, Toho Chemical Industry Co., Ltd., trade name) (5 parts) Was uniformly mixed and pulverized with an air mill to obtain a wettable powder.

Formulation Example 3 Wettable powder-2
Compound of the present invention (20 parts), Nipseal NS-K (white carbon, Tosoh Silica Co., Ltd., trade name) (20 parts), Kaolin clay (50 parts), Lunox 1000C (naphthalene sulfonate condensate, Toho Chemical) Kogyo Co., Ltd. (trade name) (5 parts) and Sorpol 5276 (nonionic surfactant, Toho Chemical Industry Co., Ltd., trade name) (5 parts) are uniformly mixed and pulverized with an air mill to obtain a wettable powder. Obtained.

Formulation Example 4 Water solvent-1
The compound of the present invention (20 parts), Lunox P-65L (alkyl allyl sulfonate, Toho Chemical Industry Co., Ltd., trade name) (3 parts), water-soluble carrier (potassium chloride) (77 parts) are uniformly mixed and pulverized. Then, a water solvent was obtained.

Formulation Example 5 Water solvent-2
The compound of the present invention (50 parts), Newcalgen BX-C (Na alkylnaphthalene sulfonate, manufactured by Takemoto Yushi-Se, trade name) (5 parts), silicon dioxide (2 parts), water-soluble carrier (43 parts) are uniformly added. Mixed and pulverized to obtain a water solvent.

Formulation Example 6 Flowable Agent-1
Pre-mixed propylene glycol (5 parts), Solpol 7933 (anionic surfactant, Toho Chemical Industry Co., Ltd., trade name) (5 parts), water (50 parts) compound of the present invention (20 parts) To form a slurry-like mixture, and then the slurry-like mixture was wet-milled with Dynomill (Shinmaru Enterprises Co., Ltd.), and then xanthan gum (0.2 parts) was well mixed and dispersed in water (19.8 parts) in advance. Was added to obtain a flowable agent.

Formulation Example 7 Flowable Agent-2
Compound of the present invention (20 parts), Newkalgen FS-26 (mixture of dioctyl sulfosuccinate and polyoxyethylene tristyryl phenyl ether, Takemoto Yushi Co., Ltd., trade name) (5 parts), propylene glycol (8 parts), Water (50 parts) was mixed in advance, and this slurry mixture was wet-milled with Dynomill (Shinmaru Enterprises Co., Ltd.). Next, xanthan gum (0.2 parts) was well mixed and dispersed in water (16.8 parts) to prepare a gel-like material, which was thoroughly mixed with the crushed slurry to obtain a flowable agent.

Formulation Example 8 EW-1
The compound of the present invention (20 parts), Solpol CA-42 (nonionic activator, Toho Chemical Industry Co., Ltd., trade name) (15 parts) and preservative Proxel GX-L (0.1 part) are mixed and homogenized. After that, water (59.6 parts) was gradually added with stirring to obtain a dispersion. Xanthan gum obtained by adding antifoaming agent Antihome E-20 (emulsion type modified silicone type, Kao Corporation, trade name) (0.1 part) to the obtained dispersion and dispersing it in propylene glycol (5.0 parts). (0.2 parts) was added to obtain an emulsion preparation (phase inversion emulsification method).

Formulation Example 9 EW-2
The compound of the present invention (10 parts) was dissolved in xylene (10 parts) and mixed with the surfactant Leodol 430V (polyoxyethylene sorbit tetraoleate, Kao Corporation, trade name) (24 parts). Liquid obtained in water (50.6 parts), antifoaming agent Antihome E-20 (emulsion type modified silicone type, Kao Corporation, trade name) (0.1 part), preservative Proxel GX-L (0 0.1 part) and then dispersed using a homogenizer, and xanthan gum (0.2 part) dispersed in propylene glycol (5.0 parts) was added to obtain an emulsion preparation (mechanical emulsification method).

Formulation Example 10 ME agent-1
After the compound of the present invention (0.01 part) and Solpol CA-42 (nonionic activator, Toho Chemical Industry Co., Ltd., trade name) (0.1 part) are mixed and homogenized, water is gradually added while stirring. (99.79 parts) was added. Preservative Proxel GX-L (0.1 part) was added to the dispersion liquid to obtain a microemulsion.

Formulation Example 11 ME agent-2
The compound of the present invention (10 parts) and Newkalgen D-945 (polyoxyethylene (20 mol) sorbitan monooleate, Takemoto Yushi Co., Ltd., trade name) (20 parts) were mixed and homogenized, and then stirred. Water (69.9 parts) was added slowly. The preservative Proxel GX-L (0.1 part) was added to the dispersion to obtain a microemulsion.

Formulation Example 12 ME agent-3
The compound of the present invention (0.01 part) was used as a solvent Solvesso 200 (0.08 part), Newkalgen ST-30 (polyoxyethylene aryl phenyl ether formaldehyde condensate, polyoxyalkylene aryl phenyl ether, alkylbenzene sulfonate and xylene). Was dissolved in Takemoto Yushi-Seiyaku Co., Ltd. (trade name) (0.12 parts), then mixed with a surfactant to homogenize, and water (99.69 parts) was gradually added with stirring. The preservative Proxel GX-L (0.1 part) was added to the dispersion to obtain a microemulsion.

Formulation Example 13 Granule-1
The compound (5 parts) of the present invention, bentonite (30 parts), clay (60 parts), sodium lignin sulfonate (5 parts) are uniformly pulverized and mixed, and after adding water well and kneading well, extrusion granulation, Dry granulation was performed to obtain granules.

Formulation Example 14 Granule-2
After adding silica sand (90 parts) to a tumbling type granulator to make it water-containing, the compound of the present invention (5 parts), sodium ligninsulfonate (4 parts), polyvinyl alcohol (PVA) ( 0.5 parts) and white carbon (0.5 parts) were added and coated, and then dried and sized to obtain granules.

Formulation Example 15 Granules-3
Ishikawa Wright (89 parts) was placed in a tumbling type granulator and hydrated, and then pulverized and mixed in advance with the compound of the present invention (5 parts), sodium ligninsulfonate (3 parts), and sodium dioctylsulfosuccinate. (0.5 parts), POE styryl phenyl ether (2 parts) and polyvinyl alcohol (PVA) (0.5 parts) were added, coated and dried to obtain granules.

Formulation Example 16 Fine Granule-1
The compound of the present invention (2 parts) was diluted with a solvent and mixed with pumice (98 parts) as a bulking agent while spraying the diluent. The obtained granular composition was dried and then sieved to obtain a fine granule.

Formulation Example 17 Fine granule-2
The compound of the present invention (5 parts) is air-milled or mechanochemically milled if necessary. The powdery raw material and silica sand (85 parts) as a bulking agent were uniformly mixed, and then a binder Toxanone GR-31A (10 parts) diluted with a solvent was sprayed and mixed, and the obtained granular composition was dried. Then, it was sieved to obtain a fine granule.

Formulation Example 18 Powder A powder was obtained by uniformly mixing and grinding the compound of the present invention (5 parts), white carbon (5 parts), and clay (trade name of Nippon Talc Co., Ltd.) (90 parts).

Formulation Example 19 DL powder A compound (5 parts) of the present invention, propylene glycol (0.5 parts) and DL clay (94.5 parts) were uniformly mixed and pulverized to obtain a powder.

Formulation Example 20 Seed coating powder The compound of the present invention (10 parts), sodium lignin sulfonate (6 parts), polyvinyl alcohol (PVA) (1 part) and clay (Nippon Talc Co., Ltd. trade name) (83 parts) are homogenized. The powder prepared by mixing and pulverizing with the above was mixed with the seed moistened in advance and air-dried to obtain a coated seed.

比較剤Ａ （国際公開第2006/087162号記載の22-11） Next, the effects and usefulness of the compound of the present invention will be described with reference to specific examples. The compounds used for comparison and control are shown by the following compound symbols.

Comparative agent A (22-11 described in WO 2006/087162)

Test Example 1: Density Suppression Test Against Nite Mites A 430 ml capacity polyethylene cup containing water was capped with a hole (diameter about 5 mm) in the center. A notch having a width of about 5 mm was made in a circular filter paper having a diameter of 6.5 cm, and a strip-shaped portion hanging downward was inserted so as to be immersed in water in a cup through a hole in a lid, and absorbent cotton was placed on the filter paper. In this way, two leaf disks (2 cm x 5 cm) made from fresh green beans were placed on absorbent cotton that had been constantly replenished with water in the cup, and 10 female adult mites on the leaf disk were placed on the leaf disks. I inoculated. This cup was placed in an acrylic cylinder having a height of 50 cm and a diameter of 10 cm, and 2.0 ml of a water-diluted solution (500 ppm) of the emulsion prepared according to Formulation Example 1 was sprayed using an air brush (1 concentration). 1 iteration). After spraying, it was kept in a constant temperature room at 25 ° C. The next-generation density suppression effect on eggs laid by adults 7 days after treatment was 100 (density suppression rate: 100%), 95 (same: 99-95%), 80 (same: 94-80%), 50 (same: 79-50%) and 0 (the same: less than 50%) were evaluated, and the next-generation density suppression rate was calculated by the following formula based on the results.
Next-generation density suppression rate = (A x 100 + B x 95 + C x 80 + D x 50) / (A + B + C + D + E)
A: 100 disks, B: 95 disks, C: 80 disks, D: 50 disks, E: 0 disks As a result, compound numbers A-1, A-2, A-3 , A-4, A-7, A-8, A-10, A-11, A-12, A-13, A-14, A-15 showed 100% density inhibition rate. . On the other hand, the comparative agent A had a density suppression rate of 0%.

Test Example 2: Adult killing test against citrus red mite A 430 ml capacity polyethylene cup containing water was capped with a hole (diameter about 5 mm) in the center. A notch having a width of about 5 mm was made in a circular filter paper having a diameter of 6.5 cm, and a strip-shaped portion hanging downward was inserted so as to be immersed in water in a cup through a hole in a lid, and absorbent cotton was placed on the filter paper. In this way, two leaf disks (diameter 2 cm) made from fully developed leaves of citrus are placed on absorbent cotton that has been constantly replenished with water in the cup, and five adult citrus mites females are placed on the leaf disks. I inoculated. This cup was placed in an acrylic cylinder having a height of 50 cm and a diameter of 10 cm, and 2.0 ml of a water-diluted solution (500 ppm) of the emulsion prepared according to Formulation Example 1 was sprayed with an air brush (1 concentration, 1 Repeat). After spraying, it was kept in a constant temperature room at 25 ° C. Four days after the treatment, the life and death and agony of the adults were examined under a binocular, and the acaricidal rate was defined as death, and the acaricidal rate (%) [(the number of dead mites / the number of mites tested) × 100] was calculated.
As a result, the compounds of the present invention of compound numbers A-2, A-4, A-8, A-13 and A-15 showed 100% miticidal rate. On the other hand, the comparative agent A had a miticidal rate of 0%.

  The 1-phenylpiperidine derivative of the present invention can be preferably used as an active ingredient of agricultural and horticultural chemicals.

Claims (14)

The following formula (1)

[In the formula, R represents a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkynyl group. C _3-6 cycloalkyl C _1-6 alkyl group or C _3-6 halocycloalkyl C _1-6 alkyl group,
X is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkenyl group, C _{2- 6} haloalkynyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _3-6 halocycloalkyl group, C _1-6 alkoxycarbonyl group, C _1-6 hydroxyalkyl group, C _{1- 6} alkoxy C _1-6 alkyl group, formyl group, halogen atom, cyano group or nitro group,
Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
Z may be the same or different and each represents a C _1-6 alkyl group,
n represents an integer of 0 or 1,
m is an integer from 1 to 3]
The 1-phenylpiperidine derivative represented by the formula, its N-oxide or a salt thereof. The 1-phenylpiperidine derivative according to claim 1, wherein R represents a C _1-6 alkyl group or a C _1-6 haloalkyl group, an N-oxide thereof or a salt thereof. X represents a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _1-6 hydroxyalkyl group, a C _1-6 alkoxy C _1-6 alkyl group, a formyl group, a halogen atom or a cyano group. The 1-phenylpiperidine derivative according to 1 or 2, its N-oxide or a salt thereof.   The 1-phenylpiperidine derivative according to any one of claims 1 to 3, wherein m represents 1, a N-oxide thereof or a salt thereof. The following formula (2)

[In the formula, R represents a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _2-6 alkenyl group, a C _2-6 haloalkenyl group, a C _2-6 alkynyl group, a C _3-6 haloalkynyl group. C _3-6 cycloalkyl C _1-6 alkyl group or C _3-6 halocycloalkyl C _1-6 alkyl group,
X is a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkenyl group, C _{2- 6} haloalkynyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _3-6 halocycloalkyl group, C _1-6 alkoxycarbonyl group, C _1-6 hydroxyalkyl group, C _{1- 6} alkoxy C _1-6 alkyl group, formyl group, halogen atom, cyano group or nitro group,
Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
Z may be the same or different and each represents a C _1-6 alkyl group,
m is an integer from 1 to 3]
A method for producing a 1-phenylpiperidine derivative represented by:
Below formula (3)

[In the formula, X, Y, Z and m are as defined in formula (2), and halo ¹ represents a halogen atom]
1-phenylpiperidine derivative represented by the following formula (4)

[In the formula, R is as defined in the formula (2)]
The manufacturing method containing the process of making it react with the thiol represented by. The following formula (3)

[In the formula, X represents a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-6 cycloalkyl group, a C _2-6 alkenyl group, a C _2-6 alkynyl group, a C _2-6 haloalkenyl group. , C _2-6 haloalkynyl group, C _1-6 alkoxy group, C _1-6 haloalkoxy group, C _3-6 halocycloalkyl group, C _1-6 alkoxycarbonyl group, C _1-6 hydroxyalkyl group , C _1-6 alkoxy C _1-6 alkyl group, formyl group, halogen atom, cyano group or nitro group,
Y represents a hydrogen atom, a halogen atom, a C _1-6 alkyl group or a C _1-6 haloalkyl group,
Z may be the same or different and each represents a C _1-6 alkyl group,
halo ¹ represents a halogen atom,
m is an integer from 1 to 3]
A method for producing a 1-phenylpiperidine derivative represented by the following formula (5)

[In the formula, X, Y and halo ¹ are as defined in formula (3), and halo ² represents a halogen atom]
And a benzene derivative represented by the following formula (6)

[In the formula, Z and m are as defined in the formula (3). ]
The manufacturing method containing the process of making it react with the piperidine derivative represented by.   An agricultural and horticultural agent comprising the 1-phenylpiperidine derivative according to any one of claims 1 to 4, an N-oxide thereof or a salt thereof.   A mite control agent for agricultural and horticultural use, containing the 1-phenylpiperidine derivative according to any one of claims 1 to 4, its N-oxide or a salt thereof.   A nematode control agent for agricultural and horticultural use, which comprises the 1-phenylpiperidine derivative according to any one of claims 1 to 4, its N-oxide or a salt thereof.   An agricultural and horticultural insect pest control agent comprising the 1-phenylpiperidine derivative according to any one of claims 1 to 4, its N-oxide or a salt thereof.   An agricultural and horticultural disease preventive agent comprising the 1-phenylpiperidine derivative according to any one of claims 1 to 4, its N-oxide or a salt thereof.   A method for controlling a pest of a plant, which comprises a step of treating a pest and / or a habitat thereof and / or a plant seed and / or a plant propagation material with the agricultural and horticultural chemical according to claim 7.   A method for preventing pests of plants, which comprises a step of treating a place where a useful crop is to be grown, a place where it is growing, or a growing crop with the agricultural and horticultural chemical according to claim 7.   A method for preparing an agrochemical composition, which comprises a step of mixing the agricultural and horticultural chemical according to claim 7 with a bulking agent and / or a surfactant.