JP4948830B2 - Ectoparasite control agent composition and ectoparasite control method - Google Patents

Description

  The present invention relates to an ectoparasite control agent composition and an ectoparasite control method. More specifically, the present invention relates to an animal ectoparasite control agent composition with enhanced photostability and a method of ectoparasite control using the same.

Etoxazole ((RS) -5-tert-butyl-2- [2- (2,6-difluorophenyl) -4,5-dihydro-1,3-oxazol-4-yl] phenetole) is an insecticide / acaricide. It is already known as an agent (Patent No. 3189001; Patent Document 1 and Patent No. 3574785; Patent Document 2), and is also known as a control agent for animal ectoparasite insects and monophagous mites (Japanese Patent Publication No. 2000). 501695; Patent Literature 3) Oxazoline compounds. However, when used outdoors, the light stability of the oxazoline compound is not sufficient, and the selection of a light stabilizer is important.
In JP-A-9-59115 (Patent Document 4), mention is made of imparting light stability to an oxazoline compound. A cyanoacrylate-based, benzotriazole-based, or benzophenone-based UV absorber described herein is used alone. Even if it is used or used together, the actual situation is that sufficient light stabilization cannot be achieved.
Also, 2,2 ′, 4,4′-tetrahydroxybenzophenone and 2,6-di-tert-butyl-4- (4,6-bis (octylthio) -1,3,5-triazin-2-ylamino) Although light stabilization by using phenol together is known (Japanese Patent Laid-Open No. 2002-114604; Patent Document 5), this relates to the inhibition of decomposition of the pyrethroid agent, and no mention is made regarding an oxazoline compound. . In addition, the combined use of UV absorbers and antioxidants of the same line does not sufficiently suppress the degradation of the active ingredients of agricultural chemicals by light, and in many cases only an additive effect can be obtained. It is mentioned that a reduction in the effect is observed.

Japanese Patent No. 3189011 Japanese Patent No. 3574785 Special Table 2000-501695 JP-A-9-59115 JP 2002-114604 A

  Accordingly, an object of the present invention is to provide an animal ectoparasite-controlling composition excellent in light stability and an ectoparasite-controlling method using the same.

  As a result of intensive studies on the photostabilization of etoxazole, the present inventors have found that a composition combining etoxazole with an ultraviolet absorber and a phenolic antioxidant exhibits a synergistic light stabilization effect. That is, by adding one or more UV absorbers and one or more phenolic antioxidants to etoxazole and using them in combination, a synergistic stabilizing effect on the photodegradation of etoxazole that is not recognized by each individual use. And the photodegradation of etoxazole was found to be significantly suppressed. Moreover, it discovered that the effect with respect to an ectoparasite was not impaired and showed remarkably high residual effect, and came to complete this invention.

（式中、Ｒ¹は水素原子、炭素数１〜１２の直鎖若しくは分枝鎖を有するアルキル基、ベンジル基または式（１）

で示される基を表し、Ｒ²は水素原子、スルホン酸基または式（２）

で示される基を表し、Ｒ³は水素原子または水酸基を表し、Ｒ⁴は水素原子、水酸基またはメトキシ基を表す。）で示されるベンゾフェノン系化合物、一般式（II）

（式中、Ｒ⁵は炭素数１〜８の直鎖または分枝鎖を有するアルキル基を表す。）で示されるシアノアクリレート系化合物、一般式（III）

（式中、Ｒ⁶は水素原子、炭素数１〜５の直鎖若しくは分枝鎖を有するアルキル基、α，α’−ジメチルベンジル基、式（３）

で示される基または式（４）

で示される基を表し、Ｒ⁷は水素原子またはオクトキシ基を表し、Ｒ⁸は水素原子、炭素数１〜８の直鎖若しくは分枝鎖を有するアルキル基、メトキシ基、α，α’−ジメチルベンジル基またはメタアクリロキシ基を表し、Ｒ⁹は水素原子または塩素原子を表す。）で示されるベンゾトリアゾール系化合物、および一般式（IＶ）

（式中、Ｒ¹⁰は水素原子または炭素数１〜８の直鎖または分枝鎖を有するアルキル基を表す。）で示されるサリチル酸系化合物から選ばれる１または２種以上の化合物を使用する前記１に記載の外部寄生虫駆除剤組成物。
３．フェノール系酸化防止剤として、一般式（Ｖ）

（式中、Ｒ¹¹は水素原子、イソプロピル基、クロロメチル基、tert−ブチル基、ベンジル基、４−メチルベンジル基またはメチルアクリレート基を表し、Ｒ¹²は水素原子またはtert−ブチル基を表し、Ｒ¹³は水素原子、メチル基、エチル基、メトキシ基、イソオクチルプロピオネート基またはステアリルプロピオネート基を表し、Ｒ¹⁴は水素原子またはメチル基を表し、Ｒ¹⁵は水素原子または炭素数１〜５の直鎖若しくは分枝鎖を有するアルキル基を表す。）で示されるモノフェノール系化合物、および下記（１）〜（１３）のビスフェノール系化合物若しくはポリフェノール系化合物：
（１）２，２’−メチレンビス（４−メチル−６−tert−ブチルフェノール）、
（２）２，２’−メチレンビス（４−エチル−６−tert−ブチルフェノール）、
（３）４，４’−チオビス（３−メチル−６−tert−ブチルフェノール）、
（４）４，４’−ブチリデンビス（３−メチル−６−tert−ブチルフェノール）、
（５）３，９−ビス［１，１−ジメチル−２−［β−（３−tert−ブチル−４−ヒドロキシ−５−メチルフェニル）プロピオニルオキシ］エチル］−２，４，８，１０−テトラオキサスピロ［５，５］ウンデカン、
（６）２，２−チオジエチレンビス［３−（３，５−ジ−tert−ブチル−４−ヒドロキシフェニル）プロピオネート］、
（７）トリエチレングリコールビス［３−（３−tert−ブチル−４−ヒドロキシ−５−メチルフェニル）プロピオネート］、
（８）１，６−ヘキサンジオールビス［３−（３，５−ジ−tert−ブチル−４−ヒドロキシフェニル）プロピオネート］、
（９）１，１，３−トリス（２−メチル−４−ヒドロキシ−５−tert−ブチルフェニル）ブタン、
（１０）１，３，５−トリメチル−２，４，６−トリス（３，５−ジ−tert−ブチル−４−ヒドロキシベンジル）ベンゼン、
（１１）テトラキス［メチレン−３−（３，５−ジ−tert−ブチル−４−ヒドロキシフェニル）プロピオネート］メタン、
（１２）トリス（３，５−ジ−tert−ブチル−４−ヒドロキシベンジル）イソシアヌレート、または、
（１３）ビス［３，３’−ビス−（４’−ヒドロキシ−３’−tert−ブチルフェニル）ブチリックアシド］グリコールエステルから選ばれる１種または２種以上の化合物を使用する前記１に記載の外部寄生虫駆除剤組成物。
４．エトキサゾール、紫外線吸収剤およびフェノール系酸化防止剤の配合割合が、質量比で１：0.05〜５：0.05〜５である前記１〜３のいずれか１項に記載の外部寄生虫駆除剤組成物。
５．前記１〜４のいずれか１項に記載の外部寄生虫駆除剤組成物を使用することを特徴とする外部寄生虫駆除方法。 That is, this invention is invention of the ectoparasite control agent composition shown below and the ectoparasite control method using the same.
1. An ectoparasite repellent composition for animals comprising etoxazole as an active ingredient and containing an ultraviolet absorber and a phenolic antioxidant.
2. As an ultraviolet absorber, the general formula (I)

(Wherein R ¹ is a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a benzyl group, or a formula (1)

In which R ² represents a hydrogen atom, a sulfonic acid group or formula (2)

R ³ represents a hydrogen atom or a hydroxyl group, and R ⁴ represents a hydrogen atom, a hydroxyl group or a methoxy group. ) Benzophenone compounds represented by general formula (II)

(Wherein R ⁵ represents a linear or branched alkyl group having 1 to 8 carbon atoms), a cyanoacrylate compound represented by the general formula (III)

(Wherein R ⁶ is a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, an α, α′-dimethylbenzyl group, a formula (3)

Or a group represented by formula (4)

R ⁷ represents a hydrogen atom or an octoxy group, R ⁸ represents a hydrogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms, a methoxy group, α, α′-dimethyl. A benzyl group or a methacryloxy group is represented, and R ⁹ represents a hydrogen atom or a chlorine atom. A benzotriazole-based compound represented by the formula (IV)

(Wherein R ¹⁰ represents a hydrogen atom or an alkyl group having a straight chain or branched chain having 1 to 8 carbon atoms) 1 or 2 or more kinds of compounds selected from salicylic acid compounds shown above are used. 2. The ectoparasite control agent composition according to 1.
3. As a phenolic antioxidant, general formula (V)

(Wherein R ¹¹ represents a hydrogen atom, isopropyl group, chloromethyl group, tert-butyl group, benzyl group, 4-methylbenzyl group or methyl acrylate group, R ¹² represents a hydrogen atom or tert-butyl group, R ¹³ is a hydrogen atom, a methyl group, an ethyl group, a methoxy group, isooctyl propionate groups or stearyl propionate group, R ¹⁴ represents a hydrogen atom or a methyl group, R ¹⁵ is 1 hydrogen atom or a carbon atoms Represents a linear or branched alkyl group of -5, and a bisphenol compound or polyphenol compound of the following (1) to (13):
(1) 2,2′-methylenebis (4-methyl-6-tert-butylphenol),
(2) 2,2′-methylenebis (4-ethyl-6-tert-butylphenol),
(3) 4,4′-thiobis (3-methyl-6-tert-butylphenol),
(4) 4,4′-butylidenebis (3-methyl-6-tert-butylphenol),
(5) 3,9-bis [1,1-dimethyl-2- [β- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy] ethyl] -2,4,8,10- Tetraoxaspiro [5,5] undecane,
(6) 2,2-thiodiethylenebis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate],
(7) Triethylene glycol bis [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionate],
(8) 1,6-hexanediol bis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate],
(9) 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane,
(10) 1,3,5-trimethyl-2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene,
(11) tetrakis [methylene-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] methane,
(12) Tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, or
(13) Said 1 which uses 1 type, or 2 or more types of compounds chosen from bis [3,3'-bis- (4'-hydroxy-3'-tert-butylphenyl) butyric acid] glycol ester Ectoparasite control agent.
4). 4. The ectoparasite repellent composition according to any one of 1 to 3, wherein a mixing ratio of etoxazole, the ultraviolet absorber and the phenolic antioxidant is 1: 0.05 to 5: 0.05 to 5 by mass ratio.
5. 5. A method for controlling ectoparasites, comprising using the ectoparasite control agent composition according to any one of 1 to 4 above.

  The animal ectoparasite repellent composition of the present invention remarkably decomposes the active ingredient etoxazole by light due to the synergistic light stabilization effect of the ultraviolet ray absorber as a component and the phenolic antioxidant. Can be suppressed. Moreover, even if it uses together an ultraviolet absorber and a phenolic antioxidant, the extermination effect with respect to an ectoparasite is not impaired. Therefore, by allowing this composition to act on animals, the ectoparasite control effect of the active ingredient can be maintained for a long period of time, and the residual effect can be remarkably increased. In particular, when used under sunlight, such as outdoors, the effect appears remarkably and is very useful as an animal ectoparasite control agent.

  The ectoparasite control agent composition of the present invention contains etoxazole as an active ingredient, and contains an ultraviolet absorber and a phenolic antioxidant as a light stabilizer.

で示されるベンゾフェノン系化合物、一般式（II）

で示されるシアノアクリレート系化合物、一般式（III）

で示されるベンゾトリアゾール系化合物、または一般式（IＶ）

で示されるサリチル酸系化合物から選ばれる１または２種以上の化合物を使用するのが好ましい。 As an ultraviolet absorber, general formula (I)

A benzophenone compound represented by the general formula (II)

A cyanoacrylate compound represented by the general formula (III)

A benzotriazole compound represented by the general formula (IV)

It is preferable to use 1 or 2 or more types of compounds chosen from the salicylic acid type compound shown by these.

で示されるモノフェノール系化合物およびビスフェノール系化合物若しくはポリフェノール系化合物から選ばれる１種または２種以上の化合物を使用するのが好ましい。 As a phenolic antioxidant, general formula (V)

It is preferable to use 1 type, or 2 or more types of compounds chosen from the monophenol type compound shown by these, a bisphenol type compound, or a polyphenol type compound.

  In the present invention, one or more ultraviolet absorbers selected from these benzophenone compounds (I), cyanoacrylate compounds (II), benzotriazole compounds (III), and salicylic acid compounds (IV); It is preferable to use a monophenol compound (V) and one or more phenolic antioxidants selected from bisphenol compounds or polyphenol compounds in combination.

で示される基を表し、Ｒ²は、水素原子、スルホン酸基または式（２）

で示される基を表し、Ｒ³は、水素原子または水酸基を表し、また、Ｒ⁴は、水素原子、水酸基またはメトキシ基を表す。 In the benzophenone-based compound represented by the above formula (I) as an ultraviolet absorber, R ¹ is a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a benzyl group, or a formula (1)

Wherein R ² represents a hydrogen atom, a sulfonic acid group, or a formula (2)

R ³ represents a hydrogen atom or a hydroxyl group, and R ⁴ represents a hydrogen atom, a hydroxyl group or a methoxy group.

In the cyanoacrylate compound represented by the formula (II), R ⁵ represents an alkyl group having a linear or branched chain having 1 to 8 carbon atoms.

で示される基または式（４）

で示される基を表し、Ｒ⁷は、水素原子またはオクトキシ基を表し、Ｒ⁸は、水素原子、炭素数１〜８の直鎖若しくは分枝鎖を有するアルキル基、メトキシ基、α，α’−ジメチルベンジル基またはメタアクリロキシ基を表し、Ｒ⁹は、水素原子または塩素原子を表す。 In the benzotriazole-based compound represented by the formula (III), R ⁶ represents a hydrogen atom, an alkyl group having a straight or branched chain having 1 to 5 carbon atoms, an α, α′-dimethylbenzyl group, a formula (3 )

Or a group represented by formula (4)

R ⁷ represents a hydrogen atom or an octoxy group, R ⁸ represents a hydrogen atom, an alkyl group having a straight or branched chain having 1 to 8 carbon atoms, a methoxy group, α, α ′. - represents a dimethylbenzyl group or methacryloxy group, R ⁹ represents a hydrogen atom or a chlorine atom.

In the salicylic acid compound represented by the formula (IV), R ¹⁰ represents a hydrogen atom or an alkyl group having a straight or branched chain having 1 to 8 carbon atoms.

R ¹¹ is a hydrogen atom, isopropyl group, chloromethyl group, tert-butyl group, benzyl group, 4-methylbenzyl group or methyl acrylate in the monophenolic compound represented by the formula (V) as a phenolic antioxidant. R ¹² represents a hydrogen atom or a tert-butyl group, R ¹³ represents a hydrogen atom, a methyl group, an ethyl group, a methoxy group, an isooctylpropionate group, or a stearylpropionate group; ¹⁴ represents a hydrogen atom or a methyl group, and R ¹⁵ represents a hydrogen atom or an alkyl group having a straight or branched chain having 1 to 5 carbon atoms.

As specific examples of the bisphenol compound or polyphenol compound,
(1) 2,2′-methylenebis (4-methyl-6-tert-butylphenol),
(2) 2,2′-methylenebis (4-ethyl-6-tert-butylphenol),
(3) 4,4′-thiobis (3-methyl-6-tert-butylphenol),
(4) 4,4′-butylidenebis (3-methyl-6-tert-butylphenol),
(5) 3,9-bis [1,1-dimethyl-2- [β- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy] ethyl] -2,4,8,10- Tetraoxaspiro [5,5] undecane,
(6) 2,2-thiodiethylenebis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate],
(7) Triethylene glycol bis [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionate],
(8) 1,6-hexanediol bis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate],
(9) 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane,
(10) 1,3,5-trimethyl-2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene,
(11) tetrakis- [methylene-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] methane,
(12) Tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, or (13) Bis [3,3′-bis- (4′-hydroxy-3′-tert-butylphenyl) Butyric acid] glycol ester and the like.

Examples of the ultraviolet absorber include the following compounds.
Benzophenone compounds:
Compound 1; 2,4-dihydroxybenzophenone,
Compound 2; 2-hydroxy-4-methoxybenzophenone,
Compound 3; 2-hydroxy-4-octoxybenzophenone,
Compound 4; 2-hydroxy-4-dodecyloxybenzophenone,
Compound 5; 2,2′-dihydroxy-4-methoxybenzophenone,
Compound 6; 2,2′-dihydroxy-4,4′-dimethoxybenzophenone,
Compound 7; 2-hydroxy-4-methoxybenzophenone-5-sulphonic acid trihydrate
Compound 8; 4-benzyloxy-2-hydroxybenzophenone,
Compound 9; 2,2′4,4′-tetrahydroxybenzophenone,
Compound 10; 1,4-bis (4-benzoyl-3-hydroxyphenoxy) butane,
Compound 11; bis (2-methoxy-4-hydroxy-5-benzoylphenyl) methane.
Cyanoacrylate compounds:
Compound 12; 2-ethylhexyl-2-cyano-3,3′-diphenyl acrylate,
Compound 13: Ethyl-2-cyano-3,3′-diphenyl acrylate.
Benzotriazole compounds:
Compound 14; 2- (2-hydroxy-5-methylphenyl) -2H-benzotriazole,
Compound 15; 2- (2-hydroxy-5-tert-butylphenyl) -2H-benzotriazole,
Compound 16; 2- (2-hydroxy-3,5-di-tert-butylphenyl) -2H-benzotriazole,
Compound 17; 5-chloro-2- (2-hydroxy-3-tert-butyl-5-methylphenyl) -2H-benzotriazole,
Compound 18; 5-chloro-2- (2-hydroxy-3,5-di-tert-butylphenyl) -2H-benzotriazole,
Compound 19; 2- (2-hydroxy-3,5-di-tert-amylphenyl) -2H-benzotriazole,
Compound 20; 2- (2H-benzotriazol-2-yl) -4-methyl-6- (3,4,5,6-tetrahydrophthalimidylmethyl) phenol,
Compound 21; 2,2′-methylenebis- [4- (1,1,3,3-tetramethylbutyl) -6- (2H-benzotriazol-2-yl) phenol],
Compound 22; 2- (2-hydroxy-4-octoxyphenyl) -2H-benzotriazole,
Compound 23; 2- (2-hydroxy-5-tert-octylphenyl) -2H-benzotriazole,
Compound 24; 2- (2-hydroxy-5-methacryloxyphenyl) -2H-benzotriazole,
Compound 25; 2- [2-hydroxy-3,5-bis (α, α'-dimethylbenzyl) phenyl] -2H-benzotriazole.
Salicylic acid compounds:
Compound 26; phenyl salicylate,
Compound 27; p-tert-butylphenyl salicylate,
Compound 28; p-octylphenyl salicylate.
Among these, compound 2; 2-hydroxy-4-methoxybenzophenone is preferable.

Examples of the phenolic antioxidant include the following compounds.
Compound A; 2-isopropyl-5-methylphenol (also known as thymol),
Compound B; 2,6-diisopropyl-4-methylphenol,
Compound C; 2-benzyl-4,6-dimethylphenol,
Compound D; 2-chloromethyl-4,6-dimethylphenol,
Compound E; 2- (4-methylbenzyl) -4,6-dimethylphenol,
Compound F; methyl-3- (2-hydroxy-5-methoxyphenyl) acrylate,
Compound G; methyl-3- (2-hydroxy-3,5-dimethylphenyl) acrylate,
Compound H; methyl-3- (2-hydroxy-3-tert-butyl-5-methoxyphenyl) acrylate,
Compound I; 2,6-di-tert-butyl-4-methylphenol,
Compound J; 2,6-di-tert-butyl-4-ethylphenol,
Compound K; a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol;
Compound L; stearyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate,
Compound M; isooctyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate,
Compound N; 2,2′-methylenebis (4-methyl-6-tert-butylphenol),
Compound O; 2,2′-methylenebis (4-ethyl-6-tert-butylphenol),
Compound P; 4,4′-thiobis (3-methyl-6-tert-butylphenol),
Compound Q; 4,4′-butylidenebis (3-methyl-6-tert-butylphenol),
Compound R; 3,9-bis [1,1-dimethyl-2- [β- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy] ethyl] -2,4,8,10- Tetraoxaspiro [5,5] undecane,
Compound S; 2,2-thiodiethylenebis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate],
Compound T; 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane,
Compound U; 1,3,5-trimethyl-2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene,
Compound V; tetrakis- [methylene-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate] methane,
Compound W; triethylene glycol bis [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionate],
Compound X; tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate,
Compound Y; 1,6-hexanediol bis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate],
Compound Z; bis [3,3′-bis- (4′-hydroxy-3′-tert-butylphenyl) butyric acid] glycol ester.
Among these, compound I; 2,6-di-tert-butyl-4-methylphenol is preferable.

In the present invention, the mixing ratio of etoxazole, UV absorber and phenolic antioxidant is 1: 0.05 to 5: 0.05 to 5, preferably 1: 0.1 to 1: 0 in terms of mass ratio. .1-1, more preferably 1: 0.1-0.5: 0.1-0.5. If the blending ratio of either UV absorber or phenolic antioxidant is too small, it will be difficult to obtain the synergistic effect of light stabilization by combined use, and if both are blended in a small amount, sufficient light stabilization will be obtained. Absent. On the other hand, it is not economical that there are too many ultraviolet absorbers and / or phenolic antioxidants.
Moreover, the blending ratio of the ultraviolet absorber and the phenolic antioxidant is preferably 1: 0.01 to 100, more preferably 1: 0.05 to 20, and still more preferably 1: 0.1 in terms of mass ratio. -10, particularly preferably 1: 0.2-5.

The ectoparasite control composition of the present invention contains etoxazole, and preferably one or more of compounds (1) to (28), and preferably one or more of compounds (A) to (Z).
Specific examples of animals to which the ectoparasite-controlling composition is applied include, for example, domestic animals such as cows, sheep, goats and chickens, and small animals such as dogs and cats.

  The ectoparasite control agent composition may be administered percutaneously to these animals as such or in a suitable formulation, administered by molded product, or applied to the environment. Transdermal administration is performed, for example, by dipping, spraying, bathing, washing, dripping (poor on), coating, spotting or dusting, and among these, dripping (poor on) and spotting are preferred. The administration by the molded product is performed by, for example, a strip, a plate, a band, or an ear tag. Application to the environment is performed by, for example, dusting, dusting, spraying, spraying, fumigation, or application, and among these, spraying and spraying are preferable.

  Suitable dosage forms include, for example, strips, plates, bands or ear tags for molded products. In addition, liquid carriers or solid carriers, and adjuvants are added, and oils, ointments, gels, emulsions, suspensions, oil-in-water emulsions, water-in-oil emulsions, wettable powders, granule wettable powders , Powders, granules or the like.

  Examples of liquid carriers include water; aliphatic or alicyclic hydrocarbons such as liquid paraffin, isoparaffin, cyclohexane, naphthene, or fumed kerosene; aromatic hydrocarbons such as xylene, trimethylbenzene, methylnaphthalene, dimethylnaphthalene, Diisopropylnaphthalene or phenylxylylethane; aliphatic alcohols such as methanol, ethanol, isopropanol, 2-ethylhexanol, n-octanol, isotridecyl alcohol, cetyl alcohol, or oleyl alcohol; aromatic alcohols such as Benzyl alcohol, phenylethanol, phenoxyethanol, etc .; esters such as ethyl acetate, butyl acetate, methyl laurate, methyl caprate, 2-ethylhexa Methyl acid, methyl oleate, isobutyl oleate, diisobutyl adipate, etc .; ketones such as methyl ethyl ketone or cyclohexanone; natural vegetable oils such as rapeseed oil, soybean oil, safflower oil, rice oil, olive oil or palm oil Synthetic glycerides such as caprylic acid triglyceride, caprylic acid mono-diglyceride, or caprylic acid / capric acid triglyceride, etc .; glycol ethers such as ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, or propylene glycol monobutyl ether Etc .; DMF; dimethylacetamide; DMSO; N-methyl-2-pyrrolidone and the like.

  Solid carriers include natural minerals such as bentonite, talc, clay, attapulgite, sepiolite, acid clay, kaolin, diatomaceous earth, or calcium carbonate; or synthetic minerals such as alumina, white carbon, calcium silicate, Examples thereof include sodium hydrogen carbonate, sodium sulfate, and potassium chloride. Organic substance powders such as sugars such as lactose, sucrose, and glucose, cellulose powder, cork powder, urea, and wheat flour can also be used.

Examples of the auxiliary agent include a surfactant, a dispersant, or a wetting agent, a fixing agent, a thickener, a freezing stabilizer, a binder, a disintegrant, and a stabilizer.
As the surfactant, dispersant, or wetting agent, nonionic surfactants, anionic surfactants, amphoteric surfactants, and the like can be used. Nonionic surfactants include, for example, polyoxyalkylene alkyl ether, polyoxyalkylene polystyryl ether, polyoxyethylene castor oil, polyoxy-polyoxypropylene copolymer, polyoxyethylene mono-di-trisorbitan fatty acid ester, Examples include sorbitol oxyethylene tetraoleate, mono fatty acid glyceride, mono sorbitan fatty acid ester, sucrose fatty acid ester, or alkyl glycoside. Examples of the anionic surfactant include sodium alkyl sulfate, sodium alkylbenzene sulfonate, or calcium salt, dialkyl sulfosuccinic acid sodium salt, naphthalene sulfonate, lignin sulfonate, polyoxyalkylene alkyl ether phosphate ester salt or sulfuric acid. Examples thereof include ester salts, polyoxyalkylene polystyryl ether phosphate esters or sulfate esters, α-olein sulfonates, alkane sulfonates, and the like. Examples of the amphoteric surfactant include N-lauryl-β-iminodipropionic acid disodium salt or lecithin.
Examples of the sticking agent include casein, gelatin, gum arabic, ammonium alginate or sodium salt and calcium carbonate, bentonite, or polyvinyl alcohol.
Examples of the thickener include heteropolysaccharides such as xanthan gum and rhamzan gum, cellulose or starch derivatives such as carboxymethylcellulose, methylcellulose, and hydroxyethyl starch, polyvinyl alcohol, polyvinylpyrrolidone, or methyl vinyl ether / maleic anhydride copolymer, montmorillonite. Clay mineral, smectite clay mineral, cation-modified montmorillonite clay mineral or smectite clay mineral, fumed silica or alkyl-modified fumed silica.
Examples of the freeze stabilizer include ethylene glycol, propylene glycol, or glycerin.
Examples of the binder include cellulose or starch derivatives such as carboxymethylcellulose, methylcellulose, and hydroxyethyl starch, or polyvinyl alcohol.
Examples of the disintegrant include carboxymethyl cellulose, dextrin, polyacrylic acid sodium salt, or isobutylene maleic anhydride copolymer.
Examples of the stabilizer include PAP (diisopropyl phosphate), epoxidized soybean oil, tall oil fatty acid, and the like.

Examples of pests for which the animal ectoparasite-controlling composition of the present invention is effective include the following.
Mild eye pests: human fleas, cat fleas, etc.
Acarid pests: Leopard mites, such as Scarlet mite, Dermatophagoides mite, Acarids, such as Staghorn mite, Scarlet mite, Mite, Mite, Mite, Mite, Mite, Mite, Mite, Mite Ticks such as ticks, ticks such as spiders, tick mites such as bird mites, etc.

When the animal ectoparasite repellent composition of the present invention is administered transdermally or by a molded product, it is appropriate to administer 1 mg to 100 mg of etoxazole per kg body weight of the applied animal. Or, when applied to the environment, it is appropriate to apply 2.5 to 250 mg / m ² etoxazole.

  In the following, the ectoparasite-controlling composition of the present invention is exemplified as a formulation example, and the present invention is further illustrated by examples and comparative examples while illustrating the anti-degradation effect test and biological effect test of etoxazole as test examples. Although described in detail, the present invention is not limited by these. In addition, “parts” in this preparation example means “parts by mass”.

Formulation Example 1: [Oil agent]
1 part of etoxazole, 0.25 part of compound (2) and 0.25 part of compound I were dissolved in 10 parts of propylene glycol monobutyl ether and dissolved in 35 parts of capryl triglyceride and 53.5 parts of liquid paraffin to prepare an oil.

Formulation Example 2: [Oil suspension]
4 parts of sorbitan monooleate, 1 part of polyoxyethylene sorbitan trioleate and 91 parts of liquid paraffin are uniformly dissolved, 1 part of etoxazole, 0.25 part of compound (1), 0.25 part of compound L, and cation-modified montmorillonite series After stirring and dispersing 2.5 parts of clay mineral, wet pulverization was performed with a bead mill to prepare an oily suspension.

Formulation Example 3: [Emulsion]
An emulsion was prepared by uniformly mixing and dissolving 5 parts of etoxazole, 1 part of Compound (26), 1 part of Compound C, 10 parts of polyoxyethylene tristyryl phenyl ether, 5 parts of calcium dodecylbenzenesulfonate, and 78 parts of xylene.

Formulation Example 4: [Aqueous Suspension]
Dissolve and disperse 5 parts of polyoxyethylene tristyryl phenyl ether phosphate ester salt, 20 parts of 1% xanthan gum aqueous solution, 1 part of montmorillonite clay mineral, and 67 parts of water, 5 parts of etoxazole, 1 part of compound (3), compound After stirring and dispersing E1 part, an aqueous suspension was prepared by wet grinding with a bead mill.

  Next, the decomposition preventing effect and biological effect of the active ingredient of the present invention will be specifically described with reference to test examples.

Test Example 1: [Decomposition prevention effect test of etoxazole oil]
Various oil agents were prepared according to Formulation Example 1 and used as examples. Moreover, the oil agent which remove | excluded only the ultraviolet absorber only from the formulation example 1, the oil agent except only the phenolic antioxidant, and the oil agent except the ultraviolet absorber and the phenolic antioxidant were prepared, and it was set as the comparative example. 200 mg of the prepared oil agent was applied to a glass petri dish having a diameter of 9 cm and then left for 2 weeks and 1 month under sunlight irradiation. Add 20 mL of n-hexane to a glass petri dish to dissolve the sample, inject 2 mL of the sample into Sep-pak (registered trademark) plus Silica cartriges, flow 5 mL of n-hexane, and discard the effluent. Next, 5 mL of ethyl acetate is poured, and the effluent is collected in an eggplant type flask. Ethyl acetate is distilled off with a rotary evaporator, and 2 mL of acetonitrile is accurately added to the residue and dissolved. Etoxazole was quantified by high performance liquid chromatography with an ultraviolet spectrophotometric detector. Moreover, the decomposition rate by sunlight exposure was calculated | required from the following formula. The results are shown in Tables 1 and 2. The integrated illuminance after 14 days and after 1 month is shown in the table of each test result. It can be seen that only when the ultraviolet absorber and the phenolic antioxidant are used in combination, the light stability of etoxazole is synergistically enhanced.

Test Example 2: [Decomposition prevention effect test of suspension in etoxazole oil]
Various suspensions in oil were prepared according to Formulation Example 2 and used as examples. Moreover, the suspension in oil except only the ultraviolet absorber from Formulation Example 2, the suspension in oil except only the phenolic antioxidant, and the suspension in oil except the ultraviolet absorber and the phenolic antioxidant An agent was prepared as a comparative example. After 200 mg of the prepared suspension in oil was applied to a glass petri dish having a diameter of 9 cm, it was left under sunlight for 2 weeks and 1 month. Add 20 mL of n-hexane to a glass petri dish to dissolve the sample, inject 2 mL of the sample into Sep-pak (registered trademark) plus Silica cartriges, flow 5 mL of n-hexane, and discard the effluent. Next, 5 mL of ethyl acetate is poured, and the effluent is collected in an eggplant type flask. Ethyl acetate is distilled off with a rotary evaporator, and 2 mL of acetonitrile is accurately added to the residue and dissolved. Etoxazole was quantified by high performance liquid chromatography with an ultraviolet spectrophotometric detector. Moreover, the decomposition rate by sunlight exposure was calculated | required similarly to Test Example 1. The results are shown in Table 3. The integrated illuminance after 14 days and 1 month was shown in the table of test results. It can be seen that the light stability of etoxazole is synergistically enhanced only when a UV absorber and a phenolic antioxidant are used in combination as in Tables 1 and 2.

Test Example 3: [Decomposition prevention effect test of etoxazole emulsion]
Various emulsions were prepared according to Formulation Example 3 and used as examples. In addition, an emulsion excluding only the ultraviolet absorber, an emulsion excluding only the phenolic antioxidant, and an emulsion excluding the ultraviolet absorber and the phenolic antioxidant were prepared from Preparation Example 3 as comparative examples. 1 g of the prepared emulsion was diluted with water to a total volume of 100 mL, and 4 mL of the diluted solution was placed in a glass petri dish having a diameter of 9 cm to evaporate the water, and then left under sunlight for 2 weeks and 1 month. 20 mL of acetonitrile is added to a glass petri dish to dissolve the sample, and the solution is collected in an eggplant type flask. Acetonitrile is distilled off with a rotary evaporator, and 2 mL of acetonitrile is accurately added to the residue and dissolved. Etoxazole was quantified by high performance liquid chromatography with an ultraviolet spectrophotometric detector. Moreover, the decomposition rate by sunlight exposure was calculated | required similarly to Test Example 1. The results are shown in Table 4. The integrated illuminance after 14 days and 1 month was shown in the table of test results. It can be seen that the photostability of etoxazole is synergistically enhanced only when a UV absorber and a phenolic antioxidant are used in the same manner as in Tables 1, 2 and 3.

Test Example 4: [Decomposition prevention effect test of etoxazole suspension in water]
Various suspensions in water were prepared according to Formulation Example 4 and used as examples. Moreover, the suspension in water except only the ultraviolet absorber, the suspension in water except only the phenolic antioxidant, and the suspension in water except the ultraviolet absorber and the phenolic antioxidant were prepared from Formulation Example 4. And it was set as the comparative example. 1 g of the prepared suspension in water was diluted with water to a total volume of 100 mL, and 4 mL of the diluted solution was placed in a glass petri dish having a diameter of 9 cm to evaporate water, and then left under sunlight for 2 weeks and 1 month. 20 mL of acetonitrile is added to a glass petri dish to dissolve the sample, and the solution is collected in an eggplant type flask. Acetonitrile is distilled off with a rotary evaporator, and 2 mL of acetonitrile is accurately added to the residue and dissolved. Etoxazole was quantified by high performance liquid chromatography with an ultraviolet spectrophotometric detector. Moreover, the decomposition rate by sunlight exposure was calculated | required similarly to Test Example 1. The results are shown in Table 5. The integrated illuminance after 14 days and 1 month was shown in the table of test results. It can be seen that the photostability of etoxazole is synergistically enhanced only when a UV absorber and a phenolic antioxidant are used in the same manner as in Tables 1, 2, 3, and 4.

Test Example 5: [Biological effect test against ticklet tick]
Etoxazole is known to have an excellent ovicidal effect, larvicidal mite effect, and juvenile mite effect, while no killing mite effect. In this test, the initial and residual effects were evaluated by the ovicidal effect. The oil agent prepared in Formulation Example 1 and the suspension in oil prepared in Formulation Example 2 are pour-on to a cow with 1 mL per 10 kg body weight using an applicator. One day after treatment, female adult ticks are released and fixed. Eggs spawned by adult ticks that have settled and sucked ticks and then fallen thawed are collected and stored at 25 ° C. After 3 weeks, the hatching status of the eggs is observed to determine the hatching rate. In addition, female ticks are released in the same manner after being raised outdoors for a month, and the hatching rate of eggs laid by adult ticks is obtained in the same manner. From this result, it can be seen that the combined use of the ultraviolet absorber and the phenolic antioxidant contributes to the extension of the residual effect of etoxazole as compared with the single use of the ultraviolet absorber or the phenolic antioxidant.

Test Example 6: [Biological effect test on cat fleas]
The emulsion prepared in Formulation Example 3 and the suspension in water prepared in Formulation Example 4 are pour-on to the cat's back and neck with 4 mL of a 100-fold water dilution per kg body weight and 2 mg as etoxazole using a microsyringe. One day after treatment, adult female fleas are released and infested. Eggs laid 4 days after the release are collected and transferred to a petri dish. The collected eggs are stored at 25 ° C., and after 3 weeks, the hatching status of the eggs is observed to determine the hatching rate. Further, after raising the cat outdoors for one month, the flea female adults are released in the same manner, and the hatching rate of the eggs laid in the same manner is obtained. From this result, it can be seen that the combined use of the ultraviolet absorber and the phenolic antioxidant contributes to the extension of the residual effect of etoxazole as compared with the single use of the ultraviolet absorber or the phenolic antioxidant.

Claims (4)

An ectoparasite repellent composition for animals containing etoxazole as an active ingredient, 2-hydroxy-4-methoxybenzophenone as an ultraviolet absorber, and 2,6-di-tert-butyl-4-methylphenol as a phenolic antioxidant object.   The ectoparasite repellent composition according to claim 1, wherein the blending ratio of etoxazole, the ultraviolet absorber and the phenolic antioxidant is 1: 0.05 to 5: 0.05 to 5 by mass ratio.   The ectoparasite control agent according to claim 2, wherein the blending ratio of the ultraviolet absorber and the phenolic antioxidant is 1: 0.2 to 5 by mass ratio. An ectoparasite control method using the ectoparasite control composition according to any one of claims 1 to 3, wherein the ectoparasite control composition is used for humans. Excluding ectoparasite control methods) .