WO2014208766A1 - Animal ectoparasite control composition - Google Patents

Abstract

An animal ectoparasite control composition has an excellent controlling effect on animal ectoparasites, said composition containing an organosulfur compound represented by formula (I) and a triester compound represented by formula (A) (for example, triethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, triisobutyl citrate, tri-tert-butyl citrate, acetyltriethyl citrate, acetyltributyl citrate, acetyltriisopropyl citrate, and the like).

Description

Animal ectoparasite control composition

The present invention relates to an animal ectoparasite control composition and an animal ectoparasite control method.

An organic sulfur compound represented by the following formula (I) is known as an active ingredient of a harmful arthropod control agent (for example, Patent Document 1).
In addition, as a method for controlling ectoparasites parasitic on animals, a method of administering an insecticidal component to animals is known (see Patent Document 2).

JP 2009-256302 A JP 2003-313104 A

The present invention provides an animal ectoparasite control composition having an excellent efficacy, comprising an organic sulfur compound represented by the following formula (I) as an active ingredient, and an animal ectoparasite control method using the composition: The issue is to provide.

As a result of intensive studies, the present inventors have found that a composition containing an organic sulfur compound represented by the following formula (I) and a triester compound represented by the following formula (A) is excellent against animal ectoparasites. The present invention has been found to have a control effect.

〔式中、Ｃｙは群Ｅ１~Ｅ２より選ばれる基で置換されていてもよいフェニル基、群Ｅ１~Ｅ２より選ばれる基で置換されていてもよい５~６員のヘテロアリール基、群Ｅ１~Ｅ３より選ばれる基で置換されていてもよい３~７員のシクロアルキル基又は群Ｅ１~Ｅ３より選ばれる基で置換されていてもよい５~７員のシクロアルケニル基を表し、
Ｒ^１はハロゲン原子で置換されていてもよいＣ１~Ｃ４鎖式炭化水素基、ハロゲン原子又は水素原子を表し、
Ｒ^２はハロゲン原子で置換されていてもよいＣ１~Ｃ４鎖式炭化水素基、−Ｃ（＝Ｇ）Ｒ^４、シアノ基、ハロゲン原子又は水素原子を表し、
Ｒ^３は少なくとも１つのフッ素原子を含むＣ１~Ｃ５ハロアルキル基又はフッ素原子を表し、
Ｇは酸素原子又は硫黄原子を表し、
Ｒ^４はハロゲン原子で置換されていてもよいＣ１~Ｃ４アルキル基、ハロゲン原子で置換されていてもよいＣ１~Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ３~Ｃ６アルケニルオキシ基、ハロゲン原子で置換されていてもよいＣ３~Ｃ６アルキニルオキシ基、ハロゲン原子で置換されていてもよいＣ１~Ｃ４アルキルアミノ基、ハロゲン原子で置換されていてもよいジ（Ｃ１~Ｃ４アルキル）アミノ基、ヒドロキシル基、アミノ基、Ｃ２~Ｃ５環状アミノ基又は水素原子を表し、
ｍは０又は１を表し、ｎは０、１又は２を表し、
群Ｅ１は、群Ｌから選ばれる基で置換されていてもよいＣ１~Ｃ６鎖式炭化水素基、ハロゲン原子で置換されていてもよいＣ３~Ｃ６シクロアルキル基、−ＯＲ^５、−ＳＲ^５、−Ｓ（＝Ｏ）Ｒ^５、−Ｓ（＝Ｏ）_２Ｒ^５、−Ｃ（＝Ｏ）Ｒ^６、−ＯＣ（＝Ｏ）Ｒ^７、シアノ基、ニトロ基、ヒドロキシル基及びハロゲン原子からなる一価基の群を表し、
群Ｅ２は、群Ｌから選ばれる基で置換されていてもよいＣ２−Ｃ６アルカンジイル基、群Ｌから選ばれる基で置換されていてもよい１，３−ブタジエン−１，４−ジイル基、−Ｇ−Ｔ−Ｇ−及び−Ｔ−Ｇ−Ｔ−からなる二価基の群を表し、
群Ｅ３は、＝Ｏ、＝ＮＯ−Ｒ^５、＝Ｃ＝ＣＨ_２及び＝Ｃ（Ｒ^８）Ｒ^９からなる二価基の群を表し、
Ｔはメチレン基又はエチレン基を表し、
Ｒ^５は群Ｌから選ばれる基で置換されていてもよいＣ１~Ｃ４鎖式炭化水素基又は群Ｌから選ばれる基で置換されていてもよいＣ３~Ｃ６シクロアルキル基を表し、
Ｒ^６はハロゲン原子で置換されていてもよいＣ１~Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ３~Ｃ６アルケニルオキシ基、ハロゲン原子で置換されていてもよいＣ３~Ｃ６アルキニルオキシ基、ハロゲン原子で置換されていてもよいＣ１~Ｃ４アルキルアミノ基、ハロゲン原子で置換されていてもよいジ（Ｃ１~Ｃ４アルキル）アミノ基、ハロゲン原子で置換されていてもよいＣ１~Ｃ４アルキル基、ヒドロキシル基、アミノ基、Ｃ２~Ｃ５環状アミノ基又は水素原子を表し、
Ｒ^７はハロゲン原子で置換されていてもよいＣ１~Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ３~Ｃ６アルケニルオキシ基、ハロゲン原子で置換されていてもよいＣ３~Ｃ６アルキニルオキシ基、ハロゲン原子で置換されていてもよいＣ１~Ｃ４アルキルアミノ基、ハロゲン原子で置換されていてもよいジ（Ｃ１~Ｃ４アルキル）アミノ基、ハロゲン原子で置換されていてもよいＣ１~Ｃ４アルキル基、アミノ基、Ｃ２~Ｃ５環状アミノ基又は水素原子を表し、
Ｒ^８およびＲ^９は同一または相異なり、ハロゲン原子で置換されていてもよいＣ１~Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ１~Ｃ４鎖式炭化水素基、ハロゲン原子又は水素原子を表し、
群Ｌは、ヒドロキシル基、ハロゲン原子で置換されていてもよいＣ１~Ｃ４アルコキシ基、ハロゲン原子で置換されていてもよいＣ３~Ｃ６アルケニルオキシ基、ハロゲン原子で置換されていてもよいＣ３~Ｃ６アルキニルオキシ基、アミノ基、ハロゲン原子で置換されていてもよいＣ１~Ｃ４アルキルアミノ基、ハロゲン原子で置換されていてもよいジ（Ｃ１~Ｃ４アルキル）アミノ基、Ｃ２~Ｃ５環状アミノ基、−Ｃ（＝Ｏ）Ｒ^６、−ＯＣ（＝Ｏ）Ｒ^７及びハロゲン原子からなる群を表す。〕
で示される有機硫黄化合物と、下記式（Ａ）

〔式中、Ｑは水素原子またはアセチル基を表し、Ｑ^１、Ｑ^２およびＱ^３は同一または相異なり、Ｃ２~Ｃ４アルキル基を表す。〕
で示されるトリエステル化合物とを含有する動物外部寄生虫防除組成物（以下、本発明組成物と記す）。
［発明２］
式（Ｉ）で示される有機硫黄化合物と、式（Ａ）で示されるトリエステル化合物との重量比が１：０．２から１：５００の範囲である発明１記載の動物外部寄生虫防除組成物。
［発明３］
式（Ｉ）で示される有機硫黄化合物と、式（Ａ）で示されるトリエステル化合物との重量比が１：０．２から１：５０の範囲である発明１記載の動物外部寄生虫防除組成物。
［発明４］
式（Ｉ）で示される有機硫黄化合物と、式（Ａ）で示されるトリエステル化合物との重量比が１：０．２から１：２０の範囲である発明１記載の動物外部寄生虫防除組成物。
［発明５］
式（Ａ）で示されるトリエステル化合物がクエン酸トリエチルである発明１~発明４のいずれか記載の動物外部寄生虫防除組成物。
［発明６］
更に（ポリ）アルキレングリコールモノアルキルエーテルを含有する発明１~発明５のいずれか記載の動物外部寄生虫防除組成物。
［発明７］
（ポリ）アルキレングリコールモノアルキルエーテルがジプロピレングリコールモノメチルエーテルである発明６記載の動物外部寄生虫防除組成物。
［発明８］
更に炭酸プロピレンを含有する発明１~発明７のいずれか記載の動物外部寄生虫防除組成物。
［発明９］
防除対象である動物外部寄生虫がノミ目、シラミ目またはダニ目の害虫である発明１~発明８のいずれか記載の動物外部寄生虫防除組成物。
［発明１０］
発明１~発明８のいずれか記載の動物外部寄生虫防除組成物の有効量を、動物に投与することを特徴とする動物外部寄生虫の防除方法。 That is, the present invention includes the following inventions.
[Invention 1]
Formula (I)

[Wherein Cy is a phenyl group which may be substituted with a group selected from groups E1 to E2, a 5- to 6-membered heteroaryl group which may be substituted with a group selected from groups E1 to E2, group E1 Represents a 3- to 7-membered cycloalkyl group optionally substituted with a group selected from ~ E3 or a 5- to 7-membered cycloalkenyl group optionally substituted with a group selected from groups E1 to E3;
R ¹ represents a C1-C4 chain hydrocarbon group optionally substituted with a halogen atom, a halogen atom or a hydrogen atom,
R ² represents a C1-C4 chain hydrocarbon group which may be substituted with a halogen atom, -C (= G) R ⁴ , a cyano group, a halogen atom or a hydrogen atom;
R ³ represents a C1-C5 haloalkyl group containing at least one fluorine atom or a fluorine atom,
G represents an oxygen atom or a sulfur atom,
R ⁴ is a C1-C4 alkyl group optionally substituted with a halogen atom, a C1-C4 alkoxy group optionally substituted with a halogen atom, a C3-C6 alkenyloxy group optionally substituted with a halogen atom, a halogen An optionally substituted C3-C6 alkynyloxy group, an optionally substituted C1-C4 alkylamino group, an optionally substituted di (C1-C4 alkyl) amino group, Represents a hydroxyl group, an amino group, a C2-C5 cyclic amino group or a hydrogen atom,
m represents 0 or 1, n represents 0, 1 or 2,
Group E1 is a C1-C6 chain hydrocarbon group which may be substituted with a group selected from Group L, a C3-C6 cycloalkyl group which may be substituted with a halogen atom, -OR ⁵ , -SR ⁵ , -S ⁽⁼ _O) ^R 5, consisting of -S (= O) 2 R 5 , -C (= O) R 6, -OC (= O) R 7, cyano group, a nitro group, a hydroxyl group and a halogen atom Represents a group of monovalent groups,
Group E2 is a C2-C6 alkanediyl group optionally substituted with a group selected from Group L, a 1,3-butadiene-1,4-diyl group optionally substituted with a group selected from Group L; Represents a group of divalent groups consisting of -G-T-G- and -T-G-T-;
Group E3 represents a group of divalent groups consisting of ═O, ═NO—R ⁵ , ═C═CH ₂ and ═C (R ⁸ ) R ⁹ ;
T represents a methylene group or an ethylene group,
R ⁵ represents a C1-C4 chain hydrocarbon group which may be substituted with a group selected from group L or a C3-C6 cycloalkyl group which may be substituted with a group selected from group L;
R ⁶ is a C1-C4 alkoxy group which may be substituted with a halogen atom, a C3-C6 alkenyloxy group which may be substituted with a halogen atom, a C3-C6 alkynyloxy group which may be substituted with a halogen atom, A C1-C4 alkylamino group optionally substituted with a halogen atom, a di (C1-C4 alkyl) amino group optionally substituted with a halogen atom, a C1-C4 alkyl group optionally substituted with a halogen atom, Represents a hydroxyl group, an amino group, a C2-C5 cyclic amino group or a hydrogen atom,
R ⁷ is a C1-C4 alkoxy group which may be substituted with a halogen atom, a C3-C6 alkenyloxy group which may be substituted with a halogen atom, a C3-C6 alkynyloxy group which may be substituted with a halogen atom, A C1-C4 alkylamino group optionally substituted with a halogen atom, a di (C1-C4 alkyl) amino group optionally substituted with a halogen atom, a C1-C4 alkyl group optionally substituted with a halogen atom, Represents an amino group, a C2-C5 cyclic amino group or a hydrogen atom;
R ⁸ and R ⁹ are the same or different and represent a C1-C4 alkoxy group which may be substituted with a halogen atom, a C1-C4 chain hydrocarbon group which may be substituted with a halogen atom, a halogen atom or a hydrogen atom. Represent,
Group L includes a hydroxyl group, a C1-C4 alkoxy group optionally substituted with a halogen atom, a C3-C6 alkenyloxy group optionally substituted with a halogen atom, and a C3-C6 optionally substituted with a halogen atom. An alkynyloxy group, an amino group, a C1-C4 alkylamino group optionally substituted with a halogen atom, a di (C1-C4 alkyl) amino group optionally substituted with a halogen atom, a C2-C5 cyclic amino group,- A group consisting of C (═O) R ⁶ , —OC (═O) R ⁷ and a halogen atom is represented. ]
And an organic sulfur compound represented by the following formula (A)

[Wherein, Q represents a hydrogen atom or an acetyl group, and Q ¹ , Q ² and Q ³ are the same or different and represent a C2 to C4 alkyl group. ]
The animal ectoparasite control composition containing the triester compound shown by these (henceforth this invention composition).
[Invention 2]
The animal ectoparasite control composition according to invention 1, wherein the weight ratio of the organic sulfur compound represented by formula (I) and the triester compound represented by formula (A) is in the range of 1: 0.2 to 1: 500. object.
[Invention 3]
The animal ectoparasite control composition according to invention 1, wherein the weight ratio of the organic sulfur compound represented by formula (I) and the triester compound represented by formula (A) is in the range of 1: 0.2 to 1:50. object.
[Invention 4]
The animal ectoparasite control composition according to invention 1, wherein the weight ratio of the organic sulfur compound represented by formula (I) to the triester compound represented by formula (A) is in the range of 1: 0.2 to 1:20. object.
[Invention 5]
The animal ectoparasite control composition according to any one of Inventions 1 to 4, wherein the triester compound represented by the formula (A) is triethyl citrate.
[Invention 6]
The animal ectoparasite control composition according to any one of Inventions 1 to 5, further comprising (poly) alkylene glycol monoalkyl ether.
[Invention 7]
The animal ectoparasite control composition according to invention 6, wherein the (poly) alkylene glycol monoalkyl ether is dipropylene glycol monomethyl ether.
[Invention 8]
The animal ectoparasite control composition according to any one of Inventions 1 to 7, further comprising propylene carbonate.
[Invention 9]
The animal ectoparasite control composition according to any one of Inventions 1 to 8, wherein the animal ectoparasite to be controlled is a flea, lice or mite pest.
[Invention 10]
An animal ectoparasite control method comprising administering an effective amount of the animal ectoparasite control composition according to any one of inventions 1 to 8 to an animal.

The composition of the present invention contains an organic sulfur compound represented by the formula (I) (hereinafter referred to as the present compound) and a triester compound represented by the formula (A) (hereinafter referred to as the present ester compound). To do.

In the pest control composition of the present invention, the weight ratio of the present compound to the present ester compound is usually 1: 0.1 to 1: 1000, preferably 1: 0.2 to 1: 500, more preferably 1. : 0.2 to 1:50, 1: 0.2 to 1:20, 1: 0.2 to 1: 8, 1: 0.2 to 1: 3, 1: 0.2 to 1: 2, 1 : 1 to 1: 2.
Is within the range.

In the present specification, the “halogen atom” means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
Examples of the “phenyl group optionally substituted with a group selected from the groups E1 to E2” include a phenyl group, 4-fluorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 4-bromophenyl group, 4- Iodophenyl group, 3,4-difluorophenyl group, 3-chloro-4-fluorophenyl group, 4-chloro-3-fluorophenyl group, 4-chloro-2-fluorophenyl group, 3,4-dichlorophenyl group, 4 -Bromo-3-fluorophenyl group, 3,4,5-trifluorophenyl group, 4-chloro-3,5-difluorophenyl group, 2,3,4,5,6-pentafluorophenyl group, 3-cyano Phenyl group, 4-cyanophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 3-methylphenyl group, 4-methylphenyl group, 2- (t (Rifluoromethyl) phenyl group, 3- (trifluoromethyl) phenyl group, 4- (trifluoromethyl) phenyl group, 4-chloro-3- (trifluoromethyl) phenyl group, 4- (1,1,2, 2,2-pentafluoroethyl) phenyl group, 4-ethynylphenyl group, 4-ethynyl-3-fluorophenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 4- (trifluoromethoxy) phenyl group, 3 Examples include-(methylthio) phenyl group, 4- (methylthio) phenyl group, 4- (trifluoromethylthio) phenyl group, and 4- (methylsulfonyl) phenyl group.

Examples of the 5- to 6-membered heteroaryl group in the “5- to 6-membered heteroaryl group optionally substituted with a group selected from the groups E1 to E2” include a 2-pyridyl group, a 3-pyridyl group, and 4- Pyridyl group of pyridyl group; pyridazinyl group of 3-pyridazinyl group and 4-pyridazinyl group; pyrimidinyl group of 2-pyrimidinyl group, 4-pyrimidinyl group and 5-pyrimidinyl group; pyrazinyl group of 2-pyrazinyl group; 1,2,4 -1,2,4-triazinyl group of triazin-3-yl group, 1,2,4-triazin-5-yl group and 1,2,4-triazin-6-yl group; -2-yl group 1,2,4-triazinyl group; 1-pyrrolyl group, 2-pyrrolyl group, pyrrolyl group of 3-pyrrolyl group; 2-furanyl group, furanyl group of 3-furanyl group 2-thienyl group, 3-thienyl thienyl group; 1-pyrazolyl group, 3-pyrazolyl group, 4-pyrazolyl group pyrazolyl group; 3-isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group isoxazolyl group; 3 -Isothiazolyl group, 4-isothiazolyl group, isothiazolyl group of 5-isothiazolyl group; 1-imidazolyl group, 2-imidazolyl group, imidazolyl group of 4-imidazolyl group; 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group Oxazolyl group; 2-thiazolyl group, 4-thiazolyl group, thiazolyl group of 5-thiazolyl group; 1,2,4-triazol-1-yl group, 1,2,4-triazol-3-yl group 1,2 , 4-triazolyl group; 1,3,4-oxadiazol-2-yl group oxadia 1,3,4-thiadiazol-2-yl group; 1,3,4-thiadiazolyl group; 1,2,4-oxadiazol-3-yl group, 1,2,4-oxadiazole- 1,2-4-diadiazolyl group of 5-yl group; 1,2,4-thiadiazolyl group of 1,2,4-thiadiazol-3-yl group, 1,2,4-thiadiazol-5-yl group It is done.
Specific examples of the “5- to 6-membered heteroaryl group optionally substituted with a group selected from groups E1 to E2” include, for example, 3-pyridyl group, 6-chloro-3-pyridyl group, 6- (tri Fluoromethyl) -3-pyridyl group, 2-pyridyl group, 5-chloro-2-pyridyl group, 5- (trifluoromethyl) -2-pyridyl group,
5-pyrimidyl group, 2-chloro-5-pyrimidyl group, 2-methoxy-5-pyrimidyl group, 2- (trifluoromethyl) -5-pyrimidyl group, 2-pyrazinyl group,
2-pyrrolyl group, 2-furanyl group, 2-thienyl group, 5-chloro-2-thienyl group, 1-pyrazolyl group, 3-isoxazolyl group, 5-tert-butyl-3-isoxazolyl group, 4-thiazolyl group, Examples include 1-imidazolyl group, 4- (trifluoromethyl) -1-imidazolyl group, 4-imidazolyl group, and 1-tert-butyl-4-imidazolyl group.

The 3- to 7-membered cycloalkyl group in the “3- to 7-membered cycloalkyl group optionally substituted with a group selected from groups E1 to E3” is a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, A cycloheptyl group and a cyclooctyl group.
Specific examples of the “3- to 7-membered cycloalkyl group optionally substituted with a group selected from groups E1 to E3” include, for example, a cyclopropyl group, a 2,2-dimethylcyclopropyl group, and 2,2-dichloro group. Cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 3-chlorocyclohexyl group, 4-chlorocyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 4- (hydroxymethyl) cyclohexyl group, 4-cyanocyclohexyl Group, 4-formylcyclohexyl group, 4- (2,2-dibromoethenyl) cyclohexyl group, 4-ethynylcyclohexyl group, 4- (4-methoxycarbonyl-1-butynyl) cyclohexyl group, 4,4-difluorocyclohexyl group 4,4-dimethylcyclohexyl group, 4- Tinyl-4-hydroxycyclohexyl group, 4-ethynyl-4-fluorocyclohexyl group, 4,4- (1,1-dichloroethylene) cyclohexyl group, 4,4- (1,1-dibromoethylene) cyclohexyl group, 4,4 -Ethylenedioxycyclohexyl group, 4,4-ethylenedithiocyclohexyl group, 3-oxocyclohexyl group, 4-oxocyclohexyl group, 4-methylenecyclohexyl group, 4- (hydroxyimino) cyclohexyl group, 4- (methoxyimino) cyclohexyl Group, 4- (ethoxyimino) cyclohexyl group, 4- (tert-butoxyimino) cyclohexyl group, 4- (allyloxyimino) cyclohexyl group and 4- (benzyloxyimino) cyclohexyl group.

Examples of the 5- to 7-membered cycloalkenyl group in the “5- to 7-membered cycloalkenyl group optionally substituted by a group selected from the groups E1 to E3” include 1-cyclopentyl, 2-cyclopentyl, and 3-cyclopentyl. 1-cyclohexenyl group, 2-cyclohexenyl group, cyclohexenyl group of 3-cyclohexenyl group; 1-cycloheptyl group, cycloheptyl group of 2-cycloheptyl group.
Specific examples of the “5- to 7-membered cycloalkenyl group optionally substituted with a group selected from the groups E1 to E3” include, for example, a 1-cyclopentyl group, 1-cyclohexyl group, 4-cyclohexenyl group, 1- Examples include a fluoro-4-cyclohexenyl group and a 1-ethynyl-4-cyclohexenyl group.

Examples of the “C1-C4 chain hydrocarbon group optionally substituted with a halogen atom” include a methyl group, an ethyl group, a propyl group, and a 1-methylethyl group (sometimes referred to as an isopropyl group), 2 , 2-dimethylpropyl group, chloromethyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 1, C1-C4 alkyl optionally substituted with a halogen atom such as 1,2,2,2-pentafluoroethyl group, 1,1-dimethylethyl group (hereinafter sometimes referred to as t-butyl group) Group: vinyl group, 2,2-difluorovinyl group, 1,2,2-trifluorovinyl group, 1-propenyl group, 2-propenyl group, 3,3-difluoro-2-propenyl group, -C2-C4 alkenyl group optionally substituted with a halogen atom such as methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-butenyl group, 2-butenyl group; ethynyl group, 1-propynyl group 3,3,3-trifluoro-1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group and the like. Examples thereof include C2-C4 alkynyl groups.

The group represented by “—C (= G) R ⁴ ” is, for example, a C1-C4 alkyl group in which G is an oxygen atom and R ⁴ is optionally substituted with a halogen atom, such as an acetyl group or a propionyl group. A group; G such as a methoxycarbonyl group and an ethoxycarbonyl group is an oxygen atom, and R ⁴ is a C1-C4 alkoxy group optionally substituted with a halogen atom; G such as an allyloxycarbonyl group is an oxygen atom; A group in which R ⁴ is a C1 to C4 alkenyloxy group optionally substituted with a halogen atom; G such as a propargyloxycarbonyl group is an oxygen atom, and C1 to C4 alkynyl in which R ⁴ is optionally substituted with a halogen atom an oxy group; N- methylcarbamoyl group, N- diethylcarbamoyl in G is an oxygen atom carbamoyl group, R ⁴ is ~ C1 may be substituted with a halogen atom C4 Group is alkylamino group; N, N-in G is an oxygen atom of dimethylcarbamoyl group, group R ⁴ is an optionally substituted di (C1 ~ C4 alkyl) even though the amino group by a halogen atom; a carboxyl group; a carbamoyl A group such as a piperidinocarbonyl group wherein G is an oxygen atom and R ⁴ is a C2-C5 cyclic amino group;

Examples of the “C1-C5 haloalkyl group containing at least one fluorine atom” include, for example, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, 1,1,2,2,2-pentafluoroethyl group, 2,2, 2-trifluoroethyl group, 1,1-difluoroethyl group, 1,1,2,2,3,3,3-heptafluoropropyl group, 1,1-difluoropropyl group, 2,2-difluoropropyl group, 3,3,3-trifluoropropyl group, 1,1,2,2,3,3,4,4,4-nonafluorobutyl group, 1,1-difluorobutyl group, 2,2-difluorobutyl group, Substituted only with fluorine atoms such as 1,1,2,2,3,3,4,4,5,5,5-undecafluoropentyl, 1,1-difluoropentyl and 2,2-difluoropentyl Is C1-C5 alkyl group; chlorodifluoromethyl group, 1,2-dichloro-1,2,2-trifluoroethyl group, 1,1-dichloro-2,2,2-trifluoroethyl group, 1-chloro- Fluorine atoms such as 1,3,3,3-tetrafluoropropyl group, 2,3-dichloro-2,3,3-trifluoropropyl group and 2,2-dichloro-3,3,3-trifluoropropyl group And a C1-C5 alkyl group substituted with a chlorine atom; 2,2-dibromo-3,3,3-trifluoropropyl group, 2-bromo-3,3,3-trifluoropropyl group, 2,3- Dibromo-3,3-difluoropropyl group, 3-bromo-3,3-difluoropropyl group, 1-bromo-1,3,3,3-tetrafluoropropyl group, 1-bromo-2,2,3,3 , 3-Pentafluoro Lopyl group, 1,3-dibromo-2,2,3,3-tetrafluoropropyl group, 3-bromo-2,3,3-trifluoropropyl group, 3-bromo-2,2,3,3-tetra A C1-C5 alkyl group substituted with a fluorine atom and a bromine atom, such as a fluoropropyl group, a 2,3-dibromo-2,3,3-trifluoropropyl group and a 3-bromo-3,3-difluoropropyl group; Can be mentioned.

Examples of the “C1-C4 alkoxy group optionally substituted with a halogen atom” include a methoxy group, an ethoxy group, a trifluoromethoxy group, and the like. Examples of the “C3-C6 alkenyloxy group optionally substituted with a halogen atom” include an allyloxy group. Examples of the “C3-C6 alkynyloxy group optionally substituted by a halogen atom” include a propargyloxy group. Examples of the “C1-C4 alkylamino group optionally substituted with a halogen atom” include a methylamino group and an ethylamino group. Examples of the “di (C1-C4 alkyl) amino group optionally substituted with a halogen atom” include a dimethylamino group and a diethylamino group.

Examples of the “C1-C6 chain hydrocarbon group optionally substituted with a group selected from group L” include a methyl group, an ethyl group, a propyl group, a 1-methylethyl group, a 2,2-dimethylpropyl group, Chloromethyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 1,1,2,2,2 -Pentafluoroethyl group, 1,1-dimethylethyl group, methoxymethyl group, ethoxymethyl group, 1-methoxyethyl group, 1-ethoxyethyl group, trifluoromethoxymethyl, (1-propenyloxy) methyl group, (2 -Propenyloxy) methyl group, (1-methyl-2-propenyloxy) methyl group, (1,1-dimethyl-2-propenyloxy) methyl group, (2,2- Difluoro-2-propenyloxy) methyl group, 1- (1-propenyloxy) ethyl group, 1- (2-propenyloxy) ethyl group, 1- (1-methyl-2-propenyloxy) ethyl group, 1- ( 1,1-dimethyl-2-propenyloxy) ethyl group, 1- (2,2-difluoro-2-propenyloxy) ethyl group, 2- (1-propenyloxy) ethyl group, 2- (2-propenyloxy) Ethyl group, 2- (1-methyl-2-propenyloxy) ethyl group, 2- (1,1-dimethyl-2-propenyloxy) ethyl group, 2- (2,2-difluoro-2-propenyloxy) ethyl Group, (2-propynyloxy) methyl group, (1-methyl-2-propynyloxy) methyl group, (1,1-dimethyl-2-propynyloxy) methyl group, Ruoxy) methyl group, (1-methyl-2-butynyloxy) methyl group, (1,1-dimethyl-2-butynyloxy) methyl group, (3,3,3-trifluoro-1-propynyloxy) methyl group, 1 -(2-propynyloxy) ethyl group, 1- (1-methyl-2-propynyloxy) ethyl group, 1- (1,1-dimethyl-2-propynyloxy) ethyl group, 1- (2-butynyloxy) ethyl Group, 1- (1-methyl-2-butynyloxy) ethyl group, 1- (1,1-dimethyl-2-butynyloxy) ethyl group, 1- (3,3,3-trifluoro-1-propynyloxy) ethyl Group, 2- (2-propynyloxy) ethyl group, 2- (1-methyl-2-propynyloxy) ethyl group, 2- (1,1-dimethyl-2-propynyloxy) ethyl group, -(2-butynyloxy) ethyl group, 2- (1-methyl-2-butynyloxy) ethyl group, 2- (1,1-dimethyl-2-butynyloxy) ethyl group, 2- (3,3,3-trifluoro -1-propynyloxy) ethyl group, hydroxymethyl group, 1-hydroxyethyl group, 1-hydroxy-1-methylethyl group, 2-hydroxyethyl group, 2-hydroxy-1-methylethyl group, etc. A C1-C6 alkyl group optionally substituted by a group;
Vinyl group, 2,2-difluorovinyl group, 1,2,2-trifluorovinyl group, 1-propenyl group, 2-propenyl group, 3,3-difluoro-2-propenyl group, 1-methyl-2-propenyl group A C2-C6 alkenyl group optionally substituted with a group selected from group L such as a group;
1-ethynyl group, 2-bromoethynyl group, 2-iodoethynyl group and 2- (methoxycarbonyl) ethynyl group, 1-propynyl group, 3-fluoro-1-propynyl group, 3,3-difluoro-1-propynyl group 3- (dimethylamino) -1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 3-methoxy-1-propynyl group, 3- (methoxycarbonyl) -1-propynyl group, 2- Propynyl, 1-fluoro-2-propynyl, 1,1-difluoro-2-propynyl, 1-butynyl, 4-fluoro-1-butynyl, 4-methoxy-1-butynyl, 4- (dimethyl Amino) -1-butynyl, 4- (methoxycarbonyl) -1-butynyl, 2-butynyl, 4-fluoro-2-butynyl, 4-methoxy-2-butyl Nyl group, 4- (dimethylamino) -2-butynyl group, 4- (methoxycarbonyl) -2-butynyl group, 3-butynyl group, 1,1-difluoro-3-butynyl group, 1-pentynyl group, 5- Fluoro-1-pentynyl group, 5-methoxy-1-pentynyl group, 5- (dimethylamino) -1-pentynyl group, 5- (methoxycarbonyl) -1-pentynyl group, 2-pentynyl group, 5-fluoro-2 -Substituted with a group selected from the group L such as a pentynyl group, 5-methoxy-2-pentynyl group, 5- (dimethylamino) -2-pentynyl group, 5- (methoxycarbonyl) -2-pentynyl group Good C2-C5 alkenyl groups are mentioned.

Examples of the “C3-C6 cycloalkyl group optionally substituted with a halogen atom” include a cyclopropyl group, a cyclohexyl group, and a 4-chlorocyclohexyl group. Examples of the group represented by “—OR ⁵ ” include a methoxy group, an allyloxy group, a cyclohexyloxy group, and the like. Examples of the group represented by “—SR ⁵ ” include a methylthio group and an allylthio group. Examples of the group represented by “—S (═O) R ⁵ ” include a methylsulfenyl group. Examples of the group represented by “—S (═O) ₂ R ⁵ ” include a methylsulfonyl group. Examples of the group represented by “—C (═O) R ⁶ ” include a formyl group, an acetyl group, a methoxycarbonyl group, a carbamoyl group, and the like. Examples of the group represented by “—OC (═O) R ⁷ ” include an acetyloxy group.

Examples of the “C2-C6 alkanediyl group optionally substituted with a group selected from group L” include ethane-1,2-diyl group, butane-1,2-diyl group and the like. Examples of the “1,3-butadiene-1,4-diyl group optionally substituted with a group selected from Group L” include 1,3-butadiene-1,4-diyl group, 2-chloro-1, Examples include 3-butadiene-1,4-diyl group, 2,3-dichloro-1,3-butadiene-1,4-diyl group, and the like. Examples of the group represented by “—GTGTG” include a methylenedioxy group and an ethylenedioxy group. Examples of the group represented by “—TGGT” include —CH ₂ —O—CH ₂ — and the like. Examples of the group represented by “═NO—R ⁵ ” include a methoxyimino group and a hydroxyimino group. Examples of the group represented by “═C (R ⁸ ) R ⁹ ” include a vinylidene group.

As the present compound, for example, in the formula (I), an organic sulfur compound in which Cy is a phenyl group optionally substituted with a group selected from groups E1 to E2;
An organic sulfur compound in which Cy is a pyridyl group optionally substituted with a group selected from groups E1 to E2 or a pyrimidyl group optionally substituted with a group selected from groups E1 to E2 in formula (I);
In the formula (I), Cy is a thienyl group optionally substituted with a group selected from groups E1 to E2, an isoxazolyl group optionally substituted with a group selected from groups E1 to E2, and a group E1 to E2 An organosulfur compound which is an imidazolyl group optionally substituted with a group selected from the above, or a pyrazolyl group optionally substituted with a group selected from the group E1 to E2;
In formula (I), an organic sulfur compound in which Cy is a cyclohexyl group optionally substituted with a group selected from groups E1 to E2 or a cyclohexenyl group optionally substituted with a group selected from groups E1 to E2 Is mentioned.

This compound is a compound described in JP2009-256302A, and can be produced, for example, by the method described in the publication.
In the present compound, when R ¹ and R ² are different from each other, a stereoisomer exists based on the asymmetric carbon to which R ¹ and R ² are bonded. What is contained in a ratio can be used.
In the composition of the present invention, one or more of the present compounds may be contained.

Specific examples of the present compound include the following present compound (113).
This compound (133):
2- [4- (Methoxyimino) cyclohexyl] -2- (3,3,3-trifluoropropylsulfonyl) acetonitrile

The ester compound is liquid at normal temperature and is usually used as a solvent. A commercial item may be used for this ester compound, and it can also manufacture it by a well-known method. Examples of the ester compound include triethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate, triisobutyl citrate, tritert-butyl citrate, acetyl triethyl citrate, acetyl tributyl citrate, and acetyl citrate. Examples include triisopropyl, preferably triethyl citrate and acetyl triethyl citrate, and more preferably triethyl citrate.
In this invention composition, you may contain 1 or more types of this ester compound.

The animal ectoparasites to which the composition of the present invention is effective include cat fleas (Ctenocephalides felis), dog fleas (Ctenocephalides canis), Xenopsylla cheopes, human fleas (Pulex irris nano) Tunga penetrans, Nosopyllus fascius, etc .;
Body lice as Anoplura (Pediculus humanus corporis), head lice (Pediculus humanus humanus), crab louse (Phthirus pubis), Ushijirami (Haematopinus eurysternus), Butajirami (Haematopinus suis), Ushihosojirami (Linognathus vituli), Kebukaushijirami (Solenopotes capillatus), sheep Trunk parasitic whiteflies (Linognathus ovillus), sheep leg parasitic whiteflies (Linognathus pedalis), goats whiteflies (Linognathus stenopsis), horse lice (Haematopinus asini) , Inujirami (Linognathus setosus), etc., Kakuagohajirami (Goniodes sissimilis) as Mallophaga pests, Maruhajirami (Goniodes gigas), sheep body louse (Damalinia ovis), Yagihajirami (Damalinia caprae), Ushihajirami (Damalinia bovis), Umahajirami (Damalinia equi, chicken hawk (Menopon gallinae), chicken nagaha lice (Lipeurus caponis), habobi nagahaji (Cuclotogaster heterographus), chick algae (Menraanthus) anthus cornutus), Inuhajirami (Trichodectes canis), Nekohajirami (Felicola subrostrata) or the like;
Mite (Haemaphysalis longicornis) Mite (Haemaphysalis flava), Mite (Dermacentor taimuicus), Mite (Dermacentor variocid) persulcatus, black legged ticks (Ixodes scapularis), lone star ticks (Amblyomma americanum), bovine ticks (Boophilus microplus), cricket mite (Rhipicephalus) sanguineus, Ixodes holocyculus, western black tick (Ixodes pacificicus), Dermacentor andersoni, Ambrymumactrum ummitomictomyum (Psoroptes spp.), Sychohizen mite spp. (Chorioptes spp.), Mimihizen tick spp. (Odetectes spp.), Hymen tick spp. (Sarcoptes spp.), Dendrobium mite spp. (Notoedres spp.), Triticus mite spp. (Knemidopcoptes spp.), Sacrotes scabiei, Acne mite spp. (Demodex spp.), Demodex canis, Ornithonysus sylvairum, Dermanyssus gallinae, Tsutsumushi spp. (Trombicula spp.), Ao chiggers (Leptotrombidium akamushi), Ikisodesu-Horoshikurasu (Ixodes holocyclus), western Kuroashimadani (Ixodes pacificus), Delmas Sentoru-Anderusoni (Dermacentor andersoni), Anburionma-Makuratamu (Ambryomma maculatum), Orunitodorusu-Herumushi (Ornithodorus hermsi), Ornithodorus turicata, Ornithonissus bacoti, Acarapis spp. (Acarapis spp.), Chailetiera spp. (Cheeletiella spp.), Ornitho chaillela spp. (Ornithocheletia spp.), Myobia spp. (Myobia spp.) Sorrelgatas spp. (Psorgates spp.), Acne mite spp. (Demodex spp.), Tsutsugamushi spp. (Trombicula spp.), Listrophorus spp. (Listrophorus spp.), Mite spp. (Acarus spp.), Kenagakonadani spp. (Tyrophagus spp.), Dust mite spp. (Caloglyphus spp.), Hypodectes spp. (Hypodectes spp.), Pterorix spp. (Pterolichus spp.), Kyusen-hizen tick spp. (Psoroptes spp.), Sychohizen mite spp. (Chorioptes spp.), Mimihizen tick spp. (Odetectes spp.), Hymen tick spp. (Sarcoptes spp.), Dendrobium mite spp. (Notoedres spp.), Triticus mite spp. (Knemidopcoptes spp.), Cytodites spp. (Cytodates spp.), Laminosioptes spp. (Laminosoptes spp) etc .;
Coleoptera (Cimex electrarius), Netite lice (Cimex hemiperterus), Redubius senilis, Sashigame spp. (Triatoma spp.), Rhodonius spp. (Rhodnius ssp.), Panthrongillus spp. (Panstrongylus ssp.), Arilus critatus and the like.
In the present invention, the animal ectoparasite is preferably a flea insect, a lice insect or a mite insect.

Examples of animals that can be administered with the composition of the present invention include animals that can serve as hosts for the animal ectoparasites. Usually, in addition to humans, there are constant temperature animals and variable temperature animals kept as domestic animals and pets. It is done. As a thermostat, for example, mammals such as humans, cows, sheep, goats, pigs, camels, deer, horses, rabbits, dogs, cats, ferrets, buffalos, donkeys, faros deer, reindeer, mice, rats, hamsters, squirrels, Examples include monkeys, minks, chinchillas, raccoons, and birds include chickens, geese, turkeys, ducks, pigeons, parrots, and quails. Examples of the variable temperature animals include turtles such as tortoises, sea turtles, green turtles, turtles, lizards, iguanas, chameleons, geckos, pythons, snakes, and cobras. Preferred are thermostats, more preferred are mammals such as dogs, cats, rabbits, cows, horses, pigs and sheep, and even more preferred are dogs and cats.

The animal ectoparasite can be controlled therapeutically, suppressively, preventively and protectively by administering an effective amount of the composition of the present invention to the animal. The composition of the present invention can provide systemic or non-systemic suppression of animal ectoparasites and can be used for all or part of the developmental stage of animal ectoparasites.

In the composition of the present invention, a mixture of the present compound and the present ester compound may be used as it is as an animal ectoparasite control agent, but it can usually be used as a preparation mixed with other additives. The composition of the present invention is preferably used as a preparation such as an oral preparation, an external preparation for skin or an injection preparation. In the composition of the present invention, the total amount of the present compound and the present ester compound is usually contained in a proportion of 0.1 to 100% by weight, preferably 0.1 to 80, more preferably 5 to 80% by weight. contains.

When administered to an animal as an oral preparation, the composition of the present invention includes, for example, animal feed, animal feed premix, animal feed concentrate, pill, solution, paste, suspension, liquid, gel, It can be used in the form of tablets, boluses, and capsules.
When administered to an animal as a skin external preparation, the composition of the present invention comprises, for example, dips, dusts, powders, sprays, shampoos, and liquids, ointments or oil-in-water or water-in-oil emulsions. It can be used in a form and can be administered by spot-on treatment, pour-on treatment, dipping, spraying, bathing, washing, attrition, or spraying.
When administered to animals as an injectable preparation, it can be administered by ruminal intramuscular injection, intramuscular injection, intravenous injection, or subcutaneous injection. Preferred administration methods include spot-on treatment and pour-on treatment of liquid agents. Spot-on treatment is a method in which a liquid preparation is usually dropped or applied to the skin of the host animal's head or back of the scapula, and pour-on treatment is usually a liquid solution along the back line of the host animal body. It is a method of pouring the preparation.

The dose of the composition of the present invention to an animal may vary depending on the target animal or the ectoparasite to be controlled, but is usually the total amount of the present compound and the present ester compound per 1 kg of the living weight of the target animal. It is 1 to 5000 mg, preferably 10 to 1000 mg, and more preferably 50 to 500 mg.

The composition of the present invention may be only the present compound and the present ester compound, but may contain components other than the present compound and the present ester compound as necessary in order to impart good properties. Examples of the component include auxiliary agents such as a solvent, a surfactant, silicone oil, a solid carrier, an antioxidant, a colorant, a light stabilizer, and an adhesive.
Specifically, the good property is that the solid insecticidal component is stably dissolved, and the wettability with respect to the animal epidermis is good.
The composition of the present invention stably dissolves a solid insecticidal component, for example, a) suppresses solid precipitation of the insecticidal component even after storage at −5 ° C. for 10 days,
b) After dripping the composition of the present invention on a petri dish, the solid deposition of the insecticidal component is suppressed even if it is allowed to stand overnight (18 hours, open condition) on a 37 ° C. plate imitating the surface of the animal body. And preferably suppress the precipitation of solids after 24 hours,
c) Four hours after administration of the composition of the present invention to a beagle dog, the same procedure was performed using a solution in which only the present compound was dissolved in dipropylene glycol monomethyl ether so that the amount of the solid deposited on the body surface was the same. The amount of solid deposited in the case is suppressed, preferably until after 7 hours,
It can be confirmed by a test method such as
The wettability of the composition of the present invention with respect to the animal's epidermis is, for example, d) The wettability when the composition of the present invention is dropped on the body surface of an animal such as a dog or a cat is dipropylene glycol monomethyl ether. It is equivalent to the wettability of a solution in which only this compound is dissolved.
e) The composition of the present invention dripped onto dog skin spreads out within 10 minutes, preferably spreads out immediately after dripping,
It can be confirmed by a test method such as

Examples of the solvent that can be contained in the composition of the present invention include alcohols such as ethanol, isopropyl alcohol, benzyl alcohol, ethylene glycol, propylene glycol, and phenoxyethanol;
(Poly) alkylene glycol monoalkyl ethers such as diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, 3-methoxy-3-methyl-1-butanol;
Alkylene glycol dialkyl ethers such as ethylene glycol dimethyl ether;
Acid amides such as N, N-dimethylformamide and N, N-dimethylacetamide;
Alkylpyrrolidones such as N-methyl-2-pyrrolidone and N-octyl-2-pyrrolidone; fatty acid esters such as isopropyl myristate;
heterocyclic compounds such as γ-butyrolactone and propylene carbonate;
Paraffin oil, triglycerides; and mixtures thereof.
In the composition of the present invention, (poly) alkylene glycol monoalkyl ether and propylene carbonate are preferable, and dipropylene glycol monomethyl ether and propylene carbonate are more preferable.
The composition of the present invention preferably contains the present compound, the present ester compound, and dipropylene glycol monomethyl ether. More preferably, the present compound, the present ester compound, propylene carbonate, and dipropylene glycol monomethyl ether are contained. Specifically, dipropylene glycol monomethyl ether is usually contained in the range of 5 to 90% by weight, preferably 5 to 85% by weight, more preferably 20 to 85% by weight, and propylene carbonate is 5 to 60% by weight. Within a range of preferably 5 to 50% by weight, more preferably 5 to 40% by weight.

Examples of nonionic surfactants include sorbitan stearate and sorbitan oleate as sorbitan fatty acid esters, and glyceryl stearate, glyceryl isostearate, glyceryl oleate, polyglyceryl stearate, polyglyceryl isostearate, olein as glycerin fatty acid esters. And polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, and polyoxyethylene styryl phenyl ether. Ethylene sorbitan fatty acid ester as palm oil fatty acid polyoxyethylene sorbitan, oleic acid polio Siethylene sorbitan, polyoxyethylene sorbitan stearate, and the like, polyoxyethylene sorbite fatty acid esters include tetraoleic acid polyoxyethylene sorbit, and others include polyoxyethylene hydrogenated castor oil, alkylphenol polyglycol ether, and the like. Can be mentioned. Examples of amphoteric surfactants include lauryl betaine and stearyl betaine as betaines, imidazoline derivatives include di-sodium N-lauryl-p-iminodipropionate, and others include lecithin. Examples of the anionic surfactant include sodium lauryl sulfate and triethanolamine lauryl sulfate as the alkyl sulfate, and polyoxyethylene lauryl ether sulfate sodium and polyoxyethylene lauryl ether sulfate triethanol as the polyoxyethylene alkyl ether sulfate. Examples include amines and the like, sodium dodecylbenzenesulfonate as the alkylbenzene sulfonate, and dioxyoxyethylene lauryl ether sodium phosphate and dipolyoxyethylene oleyl ether sodium phosphate as the polyoxyethylene alkyl ether phosphate. Is mentioned. Examples of the cationic surfactant include cetyltrimethylammonium chloride and distearyldimethylammonium chloride as alkylammonium salts.
Examples of the silicone oil include dimethyl silicone oil, highly polymerized dimethyl silicone oil, cyclic silicone oil, polyether-modified silicone oil, amino-modified silicone oil, and methylphenyl silicone oil.

Examples of solid carriers that can be contained in the composition of the present invention include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramic, and other inorganic minerals (sericite, quartz, Sulfur, activated carbon, calcium carbonate, hydrated silica, etc.), fine powders and particulates such as chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, ammonium chloride, urea, etc.), substances that are solid at room temperature (2,4,6-tri Isopropyl-1,3,5-trioxane, naphthalene, p-dichlorobenzene, camphor, adamantane, etc.), wool, silk, cotton, hemp, pulp, synthetic resin (for example, low density polyethylene, linear low density polyethylene, Polyethylene resins such as high-density polyethylene; ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymers; ethylene-methacrylic Ethylene-methacrylic acid ester copolymer such as methyl copolymer and ethylene-ethyl methacrylate copolymer; Ethylene-acrylic acid ester copolymer such as ethylene-methyl acrylate copolymer and ethylene-ethyl acrylate copolymer Polymer; Ethylene-vinyl carboxylic acid copolymer such as ethylene-acrylic acid copolymer; Ethylene-tetracyclododecene copolymer; Polypropylene resin such as propylene homopolymer and propylene-ethylene copolymer; Poly-4 -Methylpentene-1, polybutene-1, polybutadiene, polystyrene; acrylonitrile-styrene resin; styrene-based acrylonitrile-butadiene-styrene resin, styrene-conjugated diene block copolymer, hydrogenated styrene-conjugated diene block copolymer, etc. Elastomer; Fluorine tree Acrylic resins such as polymethyl methacrylate; polyamide resins such as nylon 6 and nylon 66; polyester resins such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, polycyclohexylene dimethylene terephthalate; polycarbonate, polyacetal Porous materials such as polyacrylic sulfone, polyacrylate, hydroxybenzoic acid polyester, polyetherimide, polyester carbonate, polyphenylene ether resin, polyvinyl chloride, polyvinylidene chloride, polyurethane, polyvinyl pyrrolidone, foamed polyurethane, foamed polypropylene, foamed ethylene, etc. Resin), sugars, celluloses, glass, metals, ceramics, etc. Sheet, paper, thread, foam, porous body and multifilament.

Antioxidants that can be contained in the composition of the present invention include ascorbic acid and salts thereof, citric acid and salts thereof, tocopherol, soybean lecithin, cysteine hydrochloride, dibutylhydroxytoluene (BHT), butylhydroxyanisole (BHA), curcumin, Reduced glutathione, coenzyme Q10, ethoxyquin, etc. Coloring agents include Red No. 2 (Amaranth), Red No. 3 (Erythrosin), Yellow No. 4 (Tartrazine), Green No. 3 (Fast Green FCF), Blue No. 1 (Brilliant) Edible tar dyes such as Blue FCF).
Examples of the light stabilizer that can be contained in the composition of the present invention include benzophenone compounds, and examples of the adhesive include bentonite, colloidal silicic acid, cellulose derivatives, starch derivatives, polyacrylates, natural polymers, alginates, and gelatin. It is done.

In addition, the composition of the present invention may be used in combination with or in combination with a pest control active ingredient other than the present compound, a pest repellent active ingredient, a synergist, etc., if necessary.

Pest control active ingredients other than the present compound that can be used in the composition of the present invention include pyrethroid compounds, neonicotinoid compounds, insect growth control active compounds, organophosphorus compounds, phenylpyrazole compounds, carbamates -Based compounds, benzoylurea-based compounds, and the like.
Examples of pyrethroid compounds include metfurthrin, fenpropathrin, permethrin, allethrin, d-arethrin, praretrin, cyphenothrin, phenothrin, resmethrin, empentrin, fenvalerate, cyhalothrin, cyfluthrin, etofenprox, tralomethrin, esbiothrin, transfluthrin, transfluthrin , Terareslin, profluthrin and the like. Examples of neonicotinoid compounds include acetamiprid, nitenpyram, thiacloprid, thiamethoxam, imidacloprid, dinotefuran, clothianidin and the like.
Examples of the insect growth control active compound include pyriproxyfen, mesoprene, phenoxycarb, hydroprene, diflubenzuron, chlorofluazuron, triflumuron, flufenoxuron, hexaflumuron, cyromazine, lufenuron and the like.
Examples of the organophosphorus compounds include fenitrothion, nared, fenthion, siaphos, chlorpyrifos, diazinon, calcrofos, salicione, tetrachlorbinphos, dichlorvos and the like.
Examples of the phenylpyrazole-based compound include acetoprole, ethiprole, fipronil, vaniliprole, pyriprole, pyrafluprolol, and the like. Examples of the carbamate compounds include alanic carb, bendio carb, benfura carb, BPMC, carbaryl, carbofuran, carbosulfan, cloetocarb, etiophen carb, fenobucarb, phenothio carb, phenoxy carb, furothio carb, isoprocarb, metol carb, mesomil, methioamyl, NAC, Examples include pyrimicarb, propoxyl, XMC, thiodicarb, xylylcarb, and aldicarb.
Examples of the benzoylurea compounds include bistrifluron, diafenthiuron, fluazuron, fullcycloxuron, novallon, nobiflumuron, teflubenzuron, and triazuron.

Pest repellent active ingredients that can be mixed or used in the composition of the present invention include, for example, N, N-diethyl-m-toluamide, limonene, linalool, citronellal, menthol, menthone, hinokitiol, geraniol, eucalyptol, India Xacarb, caran-3,4-diol, MGK-R-326, MGK-R-874 and BAY-KBR-3023.

As an active ingredient of a synergist that can be mixed or used in the composition of the present invention, for example, 5- [2- (2-butoxyethoxy) ethoxymethyl] -6-propyl-1,3-benzodioxole N- (2-ethylhexyl) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, octachlorodipropyl ether, isobornyl thiocyanoacetate, N- (2-ethylhexyl) -1- And isopropyl-4-methylbicyclo [2.2.2] oct-5-ene-2,3-dicarboximide.

Next, the present invention will be described in more detail with reference to test examples, but the present invention is not limited to these examples.
The pest control effect of the pest control composition of the present invention can be confirmed by, for example, the following test method.

Test example 1
Test against Haephysalis longicornis This compound (133) was mixed with each solvent (triethyl citrate, tributyl citrate, acetyl tributyl citrate, diisopropyl adipate or propylene carbonate) to a concentration of 63.6 mg / ml. Then, a chemical solution was prepared.
A filter paper was placed on the bottom of a plastic petri dish having a diameter of 9 cm, and 0.2 ml of the chemical solution was treated (the treatment amount per area was 2000 mg / m ² ). Twenty Haemaphysalis longicornis were released on the filter paper, the upper lid of the petri dish was closed, and the mixture was allowed to stand at 25 ° C. Three hours later, the state of the test insects (bitterness / lethal) was observed. The results are shown in Table 1.
The bitterness and lethality of the system treated with only the solvent not containing this compound (133) was 0% for triethyl citrate, tributyl citrate, acetyl tributyl citrate and propylene carbonate, and 10% for diisopropyl adipate. It was.

Test example 2
Test against Haephyphysalis longicornis This compound was mixed with triethyl citrate (hereinafter referred to as TEC in the table) and / or diethylene glycol monoethyl ether (hereinafter referred to as TEC) in the weight ratio (%) shown in Table 2. The composition of the present invention was prepared by mixing with EDG).
A filter paper was placed on the bottom of a plastic petri dish having a diameter of 9 cm and treated with 0.2 ml of the chemical solution. The petri dish was allowed to stand overnight, and then 20 heads of Haemaphysalis longicornis were released on the filter paper, the top lid of the petri dish was closed, and the petri dish was allowed to stand at 25 ° C. Three hours later, the state of the test insects (bitterness / lethal) was observed. The results are shown in Table 2.

Test example 3
Drop administration test for canine parasitoid mite (Rhipicephalus sanguineus) On the day before the drop administration, dogs (beagle) were inoculated with 50 test dog mites (Brown dog tick). Prior to instillation, parasitic ticks were counted.
This compound and pyriproxyfen (hereinafter referred to as Pyx in the table) are mixed with dipropylene glycol (hereinafter referred to as DPM in the table) and / or triethyl citrate in the weight ratio (%) shown in Table 3. The composition of the present invention was prepared.
The prepared composition of the present invention was applied at a dose of 0.1 ml per dog body weight (kg), and the hair on the back of the neck was scraped and directly dropped onto the skin. This was made into the test group. On the other hand, the placebo group was untreated.
On the second day after administration, the number of surviving ticks parasitic on the dog was observed. Three replicates were performed per group. The parasitic ratio and the extermination rate were calculated | required using the following formulas. The test results are shown in Table 3.

Parasitic rate and extermination rate calculation method:
-Parasitic rate (%) = number of blood sucking ticks / number of ticks inoculated x 100
・ Extermination rate (%) = (1−test area average parasitic ratio / placebo area average parasitic ratio) × 100

Test example 4
Drop administration test for cat parasitic cat flea (Ctenocephalides felis) The day before the drop administration, cats were inoculated with 100 test fleas (adult fleas).
This compound and pyriproxyfen were dissolved in dipropylene glycol monomethyl ether or triethyl citrate at a weight ratio (%) shown in Table 1 to prepare the composition of the present invention.
The prepared composition of the present invention was applied at a dose of 0.1 ml per cat body weight (kg), and the hair on the back of the neck was scraped and directly dropped onto the skin. This was made into the test group. On the other hand, the placebo group was not treated. On the second day after administration, the number of surviving fleas parasitizing the cat was observed. The test results are shown in Table 4.

Parasitic rate and extermination rate calculation method:
-Parasitic rate (%) = number of blood sucking fleas / number of flea inoculations x 100
・ Extermination rate (%) = (1−test area average parasitic ratio / placebo area average parasitic ratio) × 100
In addition, when the parasitic ratio of the test group was higher than the placebo group, it was set to 0%.

Test Example 5
Drop administration test for canine parasitoid mite (Rhipicephalus sanguineus) On the day before the drop administration, dogs (beagle) were inoculated with 50 test dog mites (Brown dog tick). Prior to instillation, parasitic ticks were counted.
The present compound and pyriproxyfen are dissolved in dipropylene glycol, propylene carbonate (hereinafter referred to as PC in the table) and / or triethyl citrate at a weight ratio (%) shown in Table 5, and the composition of the present invention. A product was prepared.
The prepared composition of the present invention was applied at a dose of 0.1 ml per dog body weight (kg), and the hair on the back of the neck was scraped and directly dropped onto the skin. This was made into the test group. On the other hand, the placebo group was untreated.
On the second day after administration, the number of surviving ticks parasitic on the dog was observed. Three replicates were performed per group. The removal rate was calculated using the following formula. The test results are shown in Table 5.

Control method:
・ Extermination rate (%) = (1−test area average number of parasitics / placebo average number of parasitics) × 100

Test Example 6
Tests against ticklet ticks (Haemaphysalis longicornis) This compound was mixed with triethyl citrate, acetyltributyl citrate (hereinafter referred to as ATBC), diisobutyl adipate (hereinafter referred to as Table) in the weight ratio (%) shown in Table 6. The composition of the present invention was prepared by mixing with DIBA and / or diethylene glycol monoethyl ether.
A filter paper was placed on the bottom of a plastic petri dish having a diameter of 9 cm and treated with 0.2 ml of the chemical solution. The petri dish was allowed to stand overnight, and then 20 heads of Haemaphysalis longicornis were released on the filter paper, the top lid of the petri dish was closed, and the petri dish was allowed to stand at 25 ° C. Three hours later, the state of the test insects (bitterness / lethal) was observed. The results are shown in Table 6.

Test Example 7
Solid Precipitation Test Solid Precipitation Inhibition Test on the Animal Body Table Compound (133), propylene carbonate, dipropylene glycol monomethyl ether, and triethyl citrate were weighed and mixed at the weight ratio shown in Table 7 to prepare a liquid agent. Prepared. The solution of each formulation was spot-on treated on beagle dogs, and the solid precipitation on the body surface was evaluated. The results are shown in Table 8.

Test Example 8
Low-temperature solubility improvement test Compound (133), propylene carbonate, dipropylene glycol monomethyl ether and triethyl citrate were weighed and mixed at a weight ratio shown in Table 9 to prepare a liquid. The liquid formulation of each formulation was preserve | saved for 10 days on -5 degreeC conditions, and the presence or absence of precipitation was observed.

Test Example 9
Skin wettability improvement test Compound (133), propylene carbonate, dipropylene glycol monomethyl ether and triethyl citrate were weighed and mixed at a weight ratio shown in Table 10 to prepare a liquid. The liquid formulation of each formulation was dropped on the dog skin to determine the wettability. The wettability was determined as Excellent when it spreads immediately after dropping, and Good when it spreads within 10 minutes after dropping, and Unacceptable when it does not spread after 1 hour. The results are shown in Table 11.

The composition of the present invention has an excellent control effect against animal ectoparasites and is useful.

Claims (10)

Formula (I)

[Wherein Cy is a phenyl group which may be substituted with a group selected from groups E1 to E2, a 5- to 6-membered heteroaryl group which may be substituted with a group selected from groups E1 to E2, group E1 Represents a 3- to 7-membered cycloalkyl group optionally substituted with a group selected from ~ E3 or a 5- to 7-membered cycloalkenyl group optionally substituted with a group selected from groups E1 to E3;
R ¹ represents a C1-C4 chain hydrocarbon group optionally substituted with a halogen atom, a halogen atom or a hydrogen atom,
R ² represents a C1-C4 chain hydrocarbon group which may be substituted with a halogen atom, -C (= G) R ⁴ , a cyano group, a halogen atom or a hydrogen atom;
R ³ represents a C1-C5 haloalkyl group containing at least one fluorine atom or a fluorine atom,
G represents an oxygen atom or a sulfur atom,
R ⁴ is a C1-C4 alkyl group optionally substituted with a halogen atom, a C1-C4 alkoxy group optionally substituted with a halogen atom, a C3-C6 alkenyloxy group optionally substituted with a halogen atom, a halogen An optionally substituted C3-C6 alkynyloxy group, an optionally substituted C1-C4 alkylamino group, an optionally substituted di (C1-C4 alkyl) amino group, Represents a hydroxyl group, an amino group, a C2-C5 cyclic amino group or a hydrogen atom,
m represents 0 or 1, n represents 0, 1 or 2,
Group E1 is a C1-C6 chain hydrocarbon group which may be substituted with a group selected from Group L, a C3-C6 cycloalkyl group which may be substituted with a halogen atom, -OR ⁵ , -SR ⁵ , -S ⁽⁼ _O) ^R 5, consisting of -S (= O) 2 R 5 , -C (= O) R 6, -OC (= O) R 7, cyano group, a nitro group, a hydroxyl group and a halogen atom Represents a group of monovalent groups,
Group E2 is a C2-C6 alkanediyl group optionally substituted with a group selected from Group L, a 1,3-butadiene-1,4-diyl group optionally substituted with a group selected from Group L; Represents a group of divalent groups consisting of -G-T-G- and -T-G-T-;
Group E3 represents a group of divalent groups consisting of ═O, ═NO—R ⁵ , ═C═CH ₂ and ═C (R ⁸ ) R ⁹ ;
T represents a methylene group or an ethylene group,
R ⁵ represents a C1-C4 chain hydrocarbon group which may be substituted with a group selected from group L or a C3-C6 cycloalkyl group which may be substituted with a group selected from group L;
R ⁶ is a C1-C4 alkoxy group which may be substituted with a halogen atom, a C3-C6 alkenyloxy group which may be substituted with a halogen atom, a C3-C6 alkynyloxy group which may be substituted with a halogen atom, A C1-C4 alkylamino group optionally substituted with a halogen atom, a di (C1-C4 alkyl) amino group optionally substituted with a halogen atom, a C1-C4 alkyl group optionally substituted with a halogen atom, Represents a hydroxyl group, an amino group, a C2-C5 cyclic amino group or a hydrogen atom,
R ⁷ is a C1-C4 alkoxy group which may be substituted with a halogen atom, a C3-C6 alkenyloxy group which may be substituted with a halogen atom, a C3-C6 alkynyloxy group which may be substituted with a halogen atom, A C1-C4 alkylamino group optionally substituted with a halogen atom, a di (C1-C4 alkyl) amino group optionally substituted with a halogen atom, a C1-C4 alkyl group optionally substituted with a halogen atom, Represents an amino group, a C2-C5 cyclic amino group or a hydrogen atom;
R ⁸ and R ⁹ are the same or different and represent a C1-C4 alkoxy group which may be substituted with a halogen atom, a C1-C4 chain hydrocarbon group which may be substituted with a halogen atom, a halogen atom or a hydrogen atom. Represent,
Group L includes a hydroxyl group, a C1-C4 alkoxy group optionally substituted with a halogen atom, a C3-C6 alkenyloxy group optionally substituted with a halogen atom, and a C3-C6 optionally substituted with a halogen atom. An alkynyloxy group, an amino group, a C1-C4 alkylamino group optionally substituted with a halogen atom, a di (C1-C4 alkyl) amino group optionally substituted with a halogen atom, a C2-C5 cyclic amino group,- A group consisting of C (═O) R ⁶ , —OC (═O) R ⁷ and a halogen atom is represented. ]
And an organic sulfur compound represented by the following formula (A)

[Wherein, Q represents a hydrogen atom or an acetyl group, and Q ¹ , Q ² and Q ³ are the same or different and represent a C2 to C4 alkyl group. ]
The animal ectoparasite control composition containing the triester compound shown by these. The animal ectoparasite control according to item 1, wherein the weight ratio of the organic sulfur compound represented by formula (I) to the triester compound represented by formula (A) is in the range of 1: 0.2 to 1: 500. Composition. The animal ectoparasite control according to item 1, wherein the weight ratio of the organic sulfur compound represented by formula (I) to the triester compound represented by formula (A) is in the range of 1: 0.2 to 1:50. Composition. The animal ectoparasite control according to item 1, wherein the weight ratio of the organic sulfur compound represented by formula (I) to the triester compound represented by formula (A) is in the range of 1: 0.2 to 1:20. Composition. The animal ectoparasite control composition according to item 1, wherein the triester compound represented by the formula (A) is triethyl citrate. The animal ectoparasite control composition according to item 1, further comprising (poly) alkylene glycol monoalkyl ether. An animal ectoparasite control composition, wherein the (poly) alkylene glycol monoalkyl ether according to item 6 is dipropylene glycol monomethyl ether. The animal ectoparasite control composition according to item 1, further comprising propylene carbonate. The animal ectoparasite control composition according to item 1, wherein the animal ectoparasite to be controlled is a flea, lice or mite pest. A method for controlling animal ectoparasites, comprising administering an effective amount of the animal ectoparasite control composition according to any one of Items 1 to 8 to an animal.