JP2002193806A - Harmful life controlling composition for mammal containing pyrazole derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a harmful life controlling agent composition for livestock and pet having high safety, easy applicability and long active life. SOLUTION: The harmful life controlling composition to be topically applied to the skin of mammal contains a compound expressed by formula (1) (R1 is a 1-4C alkyl or a 1-8C haloalkyl; R2 is H or a 1-4C alkyl; R3 is an aryl or a heteroaryl which may be substituted with H, OH, a 1-4C alkyl, a 1-4C haloalkyl, a 1-4C alkoxy, phenoxy, a 1-4C haloalkoxy, a 1-4C alkylsulfenyl, a 1-4C alkylsulfinyl, a 1-4C alkylsulfonyl, a halogen atom, nitro, cyano or the like; R4 is H, a 1-4C alkyl or a 1-4C acryl; X is N or carbon atom substituted with halogen atom; and (1) and (n) are each independently, 0, 1 or 2) as an active insecticidal component in a liquid medium.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a composition for controlling pests such as ectoparasites of mammals, especially dogs and cats, particularly fleas and mites.

[0002]

BACKGROUND OF THE INVENTION Exterminating fleas and / or mites on livestock and pets has been a problem for a long time, but in recent years it has become a particularly important problem due to the widespread breeding of small animals, especially indoors. In addition, as a request for a control agent, generally, while ensuring safety such as lower toxicity, the use method is simple, the use period of the used drug is longer, and the used amount is more. A small number reduces the burden on the user and is considered desirable.

On the other hand, WO9845274 describes that a novel 1-aryl-3-cyano-5- (het) arylalkylaminopyrazole derivative is useful as an insecticide. The compound can be used as a pesticide in various fields, for example, for agricultural and horticultural use, clothing and food-related, or livestock and pets. Although it is described that it can be sprayed, no specific method of application when used for livestock and pets is described.

[0004]

As described above, especially in the field of pet flea and / or tick control, safety is ensured, the method of use is simple, and the effective period of the drug used is longer. There is a demand for a new topical flea and / or mite control agent that is superior in that it uses less drug.

[0005]

Means for Solving the Problems In order to solve the above-mentioned problems, the present inventors have found that ectoparasites for mammals, particularly dogs and cats, particularly fleas and mites, containing the compound represented by the formula (1). As a result of intensive studies on a composition effective for the present invention, the present invention has been completed. That is, the gist of the present invention is to provide the following formula (1) in a liquid medium suitable for application to animal skin.

[0006]

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(In the above formula, R ¹ represents a C ₁ -C ₄ alkyl group or a C ₁ -C ₈ haloalkyl group, and R ² represents a hydrogen atom or a C ₁ -C ₄ alkyl group. R ³ is a hydrogen atom, a hydroxyl group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group, an optionally substituted phenoxy group, a C ₁ -C ₄ Haloalkoxy group, C ₁
Alkylsulfenyl group -C _4, alkylsulfinyl groups of C ₁ -C _4, an alkylsulfonyl group having C ₁ -C _4, halogen atom, substituted with a substituent selected from the group consisting of a nitro group and a cyano group Represents an aryl group or a heteroaryl group. R ⁴ represents a hydrogen atom, a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ acyl group. X represents a carbon atom substituted by a nitrogen atom or a halogen atom. l and n each independently represent 0, 1 or 2. A) a pesticidal composition for topical application to mammalian skin, comprising a compound represented by the formula (1) as an insecticidal active ingredient.

Hereinafter, the present invention will be described in detail.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION The pest controlling composition of the present invention comprises:
Formula (1) in a liquid medium suitable for application to animal skin
It contains the compound represented by General formula (1)
The substituent R ¹ of the compound represented by is a C ₁ to C ₅ group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group and a t-butyl group.
C ₄ linear or branched alkyl group; or difluoromethyl group, trifluoromethyl group, 2-fluoroethyl group, 2-chloroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloro Ethyl group, 3-chloropropyl group, 3-bromopropyl group, 3,3,3-trifluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentane Fluoropropyl group, 2,2-dichloro-3,3,3-trifluoropropyl group, 2,2-dichloro-3,3,3-trifluoropropyl group, 1,3-difluoro-2-propyl group, 1 1,1,3,3,3-hexafluoro-2-propyl group, 3,3,3-trichloropropyl group, 4-chlorobutyl group, 4,4,4-trifluorobutyl group,
3, 3, 4, 4, 4-pentafluorobutyl group, 5,
5,5-trifluoro-pentyl group, a linear or branched chain haloalkyl group having C ₁ -C _8, such as 6,6,6 Hekishiru group. Of these, a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ haloalkyl group is preferred.

R ² is a hydrogen atom; or methyl, ethyl, n-propyl, isopropyl, n-butyl,
C ₁ such as isobutyl group, sec-butyl group, t-butyl group, etc.
A linear or branched alkyl group -C _4. Of these, a hydrogen atom is preferred. R ³ is an aryl group such as a phenyl group or a naphthyl group; or a heteroaryl group having 3 to 8 carbon atoms and containing 1 to 3 heteroatoms arbitrarily selected from a nitrogen atom, an oxygen atom and a sulfur atom. And these may be optionally substituted with the following substituent R ⁵ .

Specifically, as R ³ ,

[0012]

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[0013] Of these, preferably,

[0014]

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(In the above formula, R ⁵ is a hydrogen atom, a hydroxyl group, C ₁
Alkyl group -C _4, haloalkyl group of C ₁ ~C _4, C ₁ ~
A C ₄ alkoxy group, an optionally substituted phenoxy group,
C ₁ -C ₄ haloalkoxy groups, C ₁ -C ₄ alkyl sulphenyl group, alkylsulfinyl group C ₁ ~C _4, C ₁ ~
And a C ₄ alkylsulfonyl group, a halogen atom, a nitro group or a cyano group; )
It is.

Preferably, R ⁵ is a hydrogen atom, a hydroxyl group, an alkyl group, an alkoxy group, a haloalkoxy group, an alkylsulfenyl group, a nitro group or a cyano group. R ⁴ is a hydrogen atom; a methyl group, an ethyl group, n- propyl group, an isopropyl group, n- butyl group, isobutyl group, sec- butyl group, a linear or branched C ₁ -C ₄ in a t- butyl group and the like A chain alkyl group; or a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group,
Isopropylcarbonyl group, n-butylcarbonyl group,
And C _{1 to} C ₄ linear or branched acyl groups such as an isobutylcarbonyl group, a sec-butylcarbonyl group and a t-butylcarbonyl group. Among preferably a hydrogen atom, a linear alkyl group of C ₁ -C _4, or a straight-chain acyl group of C ₁ -C _4.

Also, l and n are each independently 0,
1 and 2 are shown. Among the above compounds, from the viewpoints of insecticidal activity, safety, and the like, particularly preferred compounds are 1-total.
(2,6-dichloro-4-trifluoromethylphenyl) -4-fluoromethylthio-5- (pyrazine-2-
Ylmethylamino) pyrazole-3-carbonitrile,
1- (2,6-dichloro-4-trifluoromethylphenyl) -4-trifluoromethylsulfinyl-5-
(Pyrazin-2-ylmethylamino) pyrazole-3-
Examples include carbonitrile and 1- (2,6-dichloro-4-trifluoromethylphenyl) -4-difluoromethylthio-5- (pyridin-2-ylmethylamino) pyrazole-3-carbonitrile.

The 1-aryl-3-cyano-5- (het) arylalkylaminopyrazole derivative which is an insecticidal active ingredient of the present invention can be prepared by a known method such as the production method described in WO9845274 or a method analogous thereto. Can be manufactured. Examples of the liquid medium used in the present invention include ketones such as acetone; nitriles such as acetonitrile; amides such as monomethylacetamide, dimethylacetamide and dimethylformamide; ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether and diethylene glycol. Glycols such as monoethyl ether, liquid polyoxyethylene glycol, propylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol n-butyl ether and butyl diglycol; alcohols such as methanol, ethanol, isopropanol and benzyl alcohol; 2-pyrrolidone ,
Examples thereof include N-methylpyrrolidone and diethyl phthalate. These may be used alone or as a mixture, and among them, it is preferable to use at least an aliphatic alcohol such as ethanol and isopropanol.

The concentration of the compound represented by the formula (1) in the composition is preferably 1 to 20% (W / V). Moreover, the pest control composition of the present invention may be mixed with other pest control components as needed. Further, the control composition of the present invention preferably contains a crystallization inhibitor in order to prevent precipitation of the compound represented by the formula (1).

The crystallization inhibitor includes, for example, surfactants and other film-forming agents. Examples of the surfactant include anionic agents such as fatty acids, sulfonic acids or salts thereof, and alkyl sulfates or salts thereof. Surfactants; Cationic surfactants such as aliphatic amines or quaternary ammonium salts thereof, aromatic amines or quaternary ammonium salts thereof; Zwitterionic surfactants such as betaine-substituted lauryl compounds; Examples include nonionic surfactants such as ethylenated sorbitan esters, polyoxyethylenated alkyl ethers, polyglycerol esters, polyoxyethylenated aliphatic alcohols, and polyoxyethylenated fatty acids.

Examples of the film forming agent include various polyvinylpyrrolidone, polyvinyl alcohol, and a copolymer of vinyl acetate and vinylpyrrolidone. As the crystallization inhibitor, a surfactant and a film forming agent are preferably used in combination. The amount of the crystallization inhibitor is not particularly limited, but is preferably 1 to 20% (W
/ V), and particularly preferably 5 to 15% (W / V).

Further, since the control agent of the present invention is used exclusively for transdermal administration, it is, for example, butylhydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium metabisulfite, propyl gallate, thiosulfate It is preferable to contain an antioxidant commonly used in this field such as sodium or a mixture of two or more of these agents. The amount of use is not particularly limited, but is preferably 0.005 to 1% ( W /
V), and particularly preferably 0.01 to 0.05%.

The composition of the present invention comprises a concentrated emulsion, a suspension,
It is used in the form of an emulsion or a solution, and specifically, it can be used in the form of an oil, cream, ointment, liquid or the like. The pests referred to in the present invention specifically include fleas and ticks, and the fleas include general species or varieties of fleas, particularly fleas of the genus Ctenocephalides, such as cat flea and dog flea, and Xenopsylla fleas such as rat flea. And fleas belonging to the genus Pulex, such as human fleas.

Examples of mites include mites of the genus Phipicephalus, mites of the genus Ornithonyssus, such as house mites, mites of the genus Dermanyssus, mites of the genus Argas, and mites of the tsutsugamushi (Trombicula). Usually, the control agent of the present invention is preferably administered to an animal so that the amount of the compound represented by the formula (1) is 0.1 to 40 mg / kg. For dogs and cats, 0.1-5 ml, preferably 0.3-
3 ml. In addition, the dosing may be applied to an applied animal such as a cat or a dog every two to three months.

Further, as the method of administration, for example, 10 cm ² or less which is located between the animal's shoulders, in particular 5 to 10 cm ²
It is preferable to apply a spot-like coating locally on the surface area of the skin, but there is no problem if a skin lotion-like form is spread over the whole body.

[0026]

Industrial Applicability The harmful substance controlling composition for topical application to mammalian skin of the present invention has a long lasting effect on fleas and mites of mammals, especially small mammals such as cats and dogs. Is a new control agent.

────────────────────────────────────────────────── ─── of the front page continued (51) Int.Cl. ⁷ identification mark FI theme Court Bu (reference) A61K 31/497 A61K 31/497 A61P 33/00 171 A61P 33/00 171 // C07D 401/12 C07D 401 / 12 F term (reference) 4C063 BB09 CC25 DD12 EE01 EE03 4C086 AA01 BC36 BC48 GA07 GA08 MA01 MA02 MA04 MA05 NA14 ZA89 ZB39 ZC61 4H011 AC01 AC04 BA01 BB09 BB10 BC03 BC06 BC07 BC19 DA13 DA15 DA16 DA17 DD07 DH02 DH02

Claims (4)

[Claims] 1. A liquid medium suitable for application to animal skin, which is represented by the following formula (1): (In the above formula, R ¹ is a C ₁ -C ₄ alkyl group or C ₁ -C ₄
A C ₈ haloalkyl group, wherein R ² is a hydrogen atom or C
₁ to ₄ alkyl groups. R ³ represents a hydrogen atom, a hydroxyl group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group, an optionally substituted phenoxy group, a C ₁ -C ₄ haloalkoxy groups, C ₁ -C ₄ alkyl sulphenyl group, C ₁ -C ₄ the alkylsulfinyl group, an alkylsulfonyl group having C ₁ -C _4, halogen atom,
It represents an aryl group or a heteroaryl group which may be substituted with a substituent selected from the group consisting of a nitro group and a cyano group. R ⁴ represents a hydrogen atom, a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ acyl group. X represents a carbon atom substituted by a nitrogen atom or a halogen atom. l and n
Represents 0, 1 or 2 each independently. A pest controlling composition for topical application to mammalian skin, comprising the compound represented by the formula (1) as an insecticidal active ingredient. 2. R ² is a hydrogen atom and R ³ is (In the above formula, R ⁵ is a hydrogen atom, a hydroxyl group, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group, an optionally substituted phenoxy group, C ₁ a haloalkoxy group -C _4, alkyl sulphenyl group of C ₁ -C _4,
C ₁ -C ₄ the alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, a halogen atom, a nitro group, a cyano group, m represents 0, 1 or 2. 2. The control composition according to claim 1, wherein 3. The control composition according to claim 1, further comprising a crystallization inhibitor. 4. The control composition according to claim 3, wherein the composition contains 1 to 20% (W / V) of a crystallization inhibitor.