JP2015151363A - Animal ectoparasite control composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an animal ectoparasite control composition having an excellent control potency against ectoparasites that infest animals.SOLUTION: An animal ectoparasite control composition containing a nitryl compound represented by formula (I) and octyl acetate has an excellent control potency against animal ectoparasites. The composition is preferably a liquid agent that further contains a solvent, in which the nitryl compound represented by formula (I) has a solubility of 40 wt.% or more at 25°C. A weight ratio of the compound represented by formula (I) to octyl acetate is preferably within the range from 1:0.5 to 1:10.

Description

  The present invention relates to a control composition for controlling ectoparasites that parasitize on the surface of a thermostat animal (for example, dogs, cats, cows, sheep, etc.) bred as livestock or pets, and a method for controlling these ectoparasites. About.

  Nitrile compounds represented by the following formula (I) are known as active ingredients of harmful arthropod control agents (for example, Patent Document 1). Moreover, the control composition of the animal ectoparasite containing the nitrile compound shown by following formula (I) and adipic acid ester is also known (refer patent document 2).

JP 2009-256302 A JP 2011-153129 A

  The present invention provides an animal ectoparasite control composition having excellent efficacy, comprising a nitrile compound represented by the following formula (I) as an active ingredient, and a method of controlling animal ectoparasites using the composition The task is to do.

  As a result of intensive studies, the present inventor has found that a composition containing a nitrile compound represented by the following formula (I) and octyl acetate has an excellent control effect against ectoparasites. It came.

で示されるニトリル化合物と酢酸オクチルとを含有する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）で示されるニトリル化合物と酢酸オクチルとの重量比が、１：０．５から１：１０の範囲である発明１記載の外部寄生虫防除組成物。
［発明３］
式（Ｉ）で示されるニトリル化合物と酢酸オクチルとの重量比が、１：１から１：５の範囲である発明１記載の外部寄生虫防除組成物。
［発明４］
外部寄生虫防除組成物に対する酢酸オクチルの含有量が、１０〜８０重量％である発明１〜３いずれか記載の外部寄生虫防除組成物。
［発明５］
外部寄生虫防除組成物に対する酢酸オクチルの含有量が、２０〜６０重量％である発明１〜３いずれか記載の外部寄生虫防除組成物。
［発明６］
外部寄生虫防除組成物が、液剤の形態である発明１〜５いずれか記載の外部寄生虫防除組成物。
［発明７］
式（１）で示されるニトリル化合物の２５℃における溶解度が４０重量％以上である溶剤を更に含有する発明１〜６いずれか記載の外部寄生虫防除組成物。
［発明８］
式（１）で示されるニトリル化合物の２５℃における溶解度が４０重量％以上である溶剤の外部寄生虫防除組成物に対する含有量が、５〜９０重量％である発明７記載の外部寄生虫防除組成物。
［発明９］
式（１）で示されるニトリル化合物の２５℃における溶解度が４０重量％以上である溶剤の外部寄生虫防除組成物に対する含有量が、１０〜６５重量％である発明７記載の外部寄生虫防除組成物。
［発明１０］
式（１）で示されるニトリル化合物の２５℃における溶解度が４０重量％以上である溶剤が、Ｎ−メチル−２−ピロリドン、Ｎ−エチル−２−ピロリドン、プロピレングリコールモノメチルエーテル、アセトフェノン、アセト酢酸メチル、アセト酢酸エチル、γ−ブチロラクトン、ジメチルスルホキシド及び炭酸プロピレンからなる群より選ばれる少なくとも一つの溶剤である発明１〜７いずれか記載の外部寄生虫防除組成物。
［発明１１］
式（１）で示されるニトリル化合物の２５℃における溶解度が４０重量％以上である溶剤が、Ｎ−メチル−２−ピロリドン、アセト酢酸エチル及び炭酸プロピレンからなる群より選ばれる少なくとも一つの溶剤である発明１〜７いずれか記載の外部寄生虫防除組成物。
［発明１２］
防除対象である外部寄生虫が、ノミ目、シラミ目またはダニ目の害虫である発明１〜１１いずれか記載の外部寄生虫防除組成物。
［発明１３］
発明１〜１２いずれか記載の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外部寄生虫の防除方法。 That is, the present invention includes the following inventions.
[Invention 1]
Formula (I)

An ectoparasite control composition containing a nitrile compound represented by formula (II) and octyl acetate (hereinafter referred to as the present invention composition).
[Invention 2]
The ectoparasite control composition according to invention 1, wherein the weight ratio of the nitrile compound represented by formula (I) to octyl acetate is in the range of 1: 0.5 to 1:10.
[Invention 3]
The ectoparasite control composition according to invention 1, wherein the weight ratio of the nitrile compound represented by formula (I) to octyl acetate is in the range of 1: 1 to 1: 5.
[Invention 4]
The ectoparasite control composition according to any one of Inventions 1 to 3, wherein the content of octyl acetate relative to the ectoparasite control composition is 10 to 80% by weight.
[Invention 5]
The ectoparasite control composition according to any one of Inventions 1 to 3, wherein the content of octyl acetate relative to the ectoparasite control composition is 20 to 60% by weight.
[Invention 6]
The ectoparasite control composition according to any one of Inventions 1 to 5, wherein the ectoparasite control composition is in the form of a solution.
[Invention 7]
The ectoparasite control composition according to any one of Inventions 1 to 6, further comprising a solvent having a solubility of the nitrile compound represented by the formula (1) at 25 ° C. of 40% by weight or more.
[Invention 8]
The ectoparasite control composition according to invention 7, wherein the nitrile compound represented by formula (1) has a solubility at 25 ° C. of 40% by weight or more based on the ectoparasite control composition in an amount of 5 to 90% by weight. object.
[Invention 9]
The ectoparasite control composition according to invention 7, wherein the content of the nitrile compound represented by formula (1) at 25 ° C. in the solvent with respect to the ectoparasite control composition is 10 to 65% by weight. object.
[Invention 10]
A solvent in which the solubility of the nitrile compound represented by the formula (1) at 25 ° C. is 40% by weight or more is N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, propylene glycol monomethyl ether, acetophenone, methyl acetoacetate The ectoparasite control composition according to any one of Inventions 1 to 7, which is at least one solvent selected from the group consisting of ethyl acetoacetate, γ-butyrolactone, dimethyl sulfoxide and propylene carbonate.
[Invention 11]
The solvent having a solubility of the nitrile compound represented by the formula (1) at 25 ° C. of 40% by weight or more is at least one solvent selected from the group consisting of N-methyl-2-pyrrolidone, ethyl acetoacetate and propylene carbonate. The ectoparasite control composition in any one of invention 1-7.
[Invention 12]
The ectoparasite control composition according to any one of Inventions 1 to 11, wherein the ectoparasite to be controlled is a flea, lice or mite pest.
[Invention 13]
A method for controlling ectoparasites, comprising administering an effective amount of the ectoparasite control composition according to any one of inventions 1 to 12 to an animal.

  The composition of the present invention has excellent efficacy in controlling ectoparasites that parasitize on the surface of a thermostat animal raised as a domestic animal or pet.

  The composition of the present invention contains a nitrile compound represented by the formula (I) (hereinafter referred to as the present compound) and octyl acetate.

  This compound is a compound described in JP2009-256302A, and can be produced, for example, by the method described in Production Example 32 of the publication.

  In the pest control composition of the present invention, the weight ratio of the present compound to octyl acetate is usually 1: 0.1 to 1: 1000, preferably 1: 0.2 to 1:50, more preferably 1: 0. Within the range of 5 to 1:10, more preferably 1: 1 to 1: 5.

Octyl acetate is a compound that is liquid (melting point: −93 ° C.) at room temperature (25 ° C.). Octyl acetate may use a commercial item, and can also be manufactured by a well-known method. Octyl acetate is a liquid having a solubility of about 19% by weight at 25 ° C. of the present compound.
The content of octyl acetate is usually 1 to 90% by weight, preferably 10 to 80% by weight, more preferably 20 to 60% by weight, based on the composition of the present invention.

The composition of the present invention is preferably in the form of a liquid agent. Furthermore, the composition of the present invention more preferably further contains a solvent (hereinafter referred to as an auxiliary solvent) having a solubility of the compound at 25 ° C. of 40% by weight or more. That is, the composition of the present invention is preferably an ectoparasite control composition containing the present compound, octyl acetate, and an auxiliary solvent.
In the present invention, the liquid agent means a liquid formulation form having a high fluidity (low viscosity) without solid precipitation at room temperature (25 ° C.).
A solution containing the present compound, octyl acetate and a co-solvent can be used favorably in an administration method called spot-on or pour-on, and solid precipitation of the present compound is suppressed even in storage at low temperature conditions. In the present invention, the auxiliary solvent is an organic solvent which is mixed with octyl acetate without separation and does not cause layer separation in the range from room temperature to low temperature (for example, −5 ° C.).

The solubility of the present compound at 25 ° C. of 40% by weight or more means that the concentration (w / w) of the solvent in a saturated solution of the present compound is 40% by weight or more at 25 ° C.
The auxiliary solvent may be a single liquid compound or a combination of a plurality of liquid compounds as long as the solubility of the present compound at 25 ° C. is 40% by weight or more.
Examples of the auxiliary solvent that can be used in the present invention include acetophenone (melting point: 21 ° C., solubility: 41%), propylene glycol monomethyl ether (melting point: −97 ° C., solubility: 40%), methyl acetoacetate (melting point: −80 ° C, solubility: 42%), ethyl acetoacetate (melting point: -43 ° C, solubility: 41%), N-methyl-2-pyrrolidone (melting point: -23 ° C, solubility: 64%), N-ethyl-2- Pyrrolidone (melting point: −77 ° C.), γ-butyrolactone (melting point: −44 ° C., solubility: 55%), propylene carbonate (melting point: −49 ° C., solubility: 46%) and dimethyl sulfoxide (melting point: 18 ° C., solubility) : 72%), and two or more mixed solvents of the solvent. In the present invention, the auxiliary solvent is preferably at least one solvent selected from the group consisting of ethyl acetoacetate, N-methyl-2-pyrrolidone and propylene carbonate. The auxiliary solvent preferably has a melting point of -20 ° C or lower.
The content of the auxiliary solvent is usually 5 to 99% by weight, preferably 10 to 75% by weight, and more preferably 10 to 65% by weight with respect to the composition of the present invention.
In the composition of the present invention, the present compound is preferably 0.1 to 30% by weight, octyl acetate is 10 to 80% by weight, and the auxiliary solvent is 10 to 89.9% by weight, more preferably the present compound is 10 to 30% by weight. % By weight, 20 to 60% by weight of octyl acetate, and 10 to 70% by weight of auxiliary solvent.

Specifically, the solubility of the present compound at 25 ° C. is measured, for example, by the following method.
Example of solubility measurement method: 100 mg of this compound was weighed into an Eppendorf tube, and 100 μL of the solvent was weighed. While keeping the temperature at 25 ° C., the mixture was stirred for 5 minutes every hour with a vortex mixer, and the operation of keeping and stirring was repeated 5 times (operation 1). When the present compound was completely dissolved, an additional 100 mg of the present compound was added, and the operations of heat retention and stirring were repeated 5 times (operation 2). Operation 2 was repeated until a part of the compound was insoluble, and when insolubility of the compound was observed, the Eppendorf tube was attached to a centrifuge (12000 rpm, 10 minutes), and the supernatant was collected. The amount of the present compound contained in the collected supernatant (saturated solution) was quantitatively analyzed by HPLC to determine the solubility (% by weight).

Ectoparasites for which the composition of the present invention is effective include fleas such as cat fleas (Ctenocephalides felis), dog fleas (Ctenocephalides canis), Xenopsylla cheopis, human fleas (Pulex irritans), sun fleas (Tunga) penetrans), European rat minnow (Nosopsyllus fasciatus), etc .;
Japanese lice (Pediculus humanus corporis), head lice (Pediculus humanus humanus), white lice (Phthirus pubis), cattle lice (Haematopinus eurysternus), pig lice (Haematopinus suis), cattle white lice (Linognes lice) Trunk parasitic whiteflies (Linognathus ovillus), sheep leg parasitic whiteflies (Linognathus pedalis), goats whitefly (Linognathus stenopsis), horse lice (Haematopinus asini), lice mosquito ), Bald lice (Goniodes gigas), sheep lice (Damalinia ovis), goat lice (Damalinia caprae), bull lice (Damalinia bovis), horse lice (Damalinia equi), chick lice (Menopon gallinae), chicks (Lipeurus caponis), Haba Biro Naga biting lice (Cuclotogaster heterographus), chicken giant louse (Menacanthus stramineus), chicken horn body louse (Menacanthus cornutus), Inuhajirami (Trichodectes canis), Nekohajirami (Felicola subrostrata) or the like;
Amblyomma americanum, Amblyomma maculatum and other Amblyomma, Boophilus microplus, Boophilus annulatus and other Boophilus, American dock tic (Dermacentor variabilis) , Dermacentor such as Dermacentor taiwanicus, Dermacentor andersoni, Dermacentor reticulatus, Haemaphysalis longicornis, Haphysali tick (Haemaphysalis longicornis), ) Haemaphysalis, Ixodes ovatus, Ixodes persulcatus, Black-legged tick (Ixodes scapularis), Western black tick (Ixodes pacificus), Ixodes Ixodes such as Ixodes holocyclus, Ixodes ricinus, Rhipicephalus sanguineus, Rhipicephalus such as Rhipicephalus appendiculatus, Arsi gassi Ornithodorus, such as Ornithodorus hermsi, Ornithodorus turicata, Psoroptes ovis, Kunsen dans emis, mutus emis opt Knemidocoptes, such as Notoedres cati, Notoedres, such as mouse-tolerant mud, Sarcoptes, such as Sarcoptes scabiei, Octo Otodectes, such as dectes cynotis, Listrophorus, such as Listrophorus gibbus, Chickoptus spp., Hypodectes spp., Pterolichus spp., Cytodites sp. , Laminosioptes spp., Dermanyssus such as Dermanyssus gallinae, Ornithonyssus such as Ornithonyssus sylviarum, Ornithonyssus such as Ornithonyssus bacoti; Cheyletiella yasguri), catlet mite (Cheyletiella blakei) and other Cheyletiella, Ornithocheyletia spp. , Psorergates spp., Trombicula akamushi, ft Trombicula species such as Trombicula pallida and Trombicula scutellaris.
Colex lectularius, Cimex hemipterus, Reduvius senilis, red turtle spp. (Triatoma spp.), Rodnius spp. (Rhodnius ssp.), Panstrons spp. (Panstrongylus ssp.), Arilus critatus and the like.
In the present invention, the 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 ectoparasites, and usually include thermostats and variable temperature animals kept as livestock or pets. 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, and fur animals such as mink, chinchilla, and raccoon. Examples of birds include chickens, geese, turkeys, ducks, pigeons, parrots, and quails. Preferred are mammals such as mice, rats, hamsters, dogs, cats, rabbits, cows, horses, pigs and sheep, and more preferred are mice, dogs and cats.

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

  In the present invention, a composition obtained by simply mixing the present compound and octyl acetate may be used for controlling ectoparasites in animals, but a liquid obtained by mixing the present compound, octyl acetate and a co-solvent is externally used. The method used for parasite control is preferred. 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, octyl acetate and auxiliary solvent is usually contained in a proportion of 20 to 100% by weight, preferably 50 to 100, more preferably 70 to 100% by weight. .

When administered to animals as a skin external preparation, the composition of the present invention can be used, for example, in the form of a dip, spray, shampoo, and liquid, ointment or oil-in-water or water-in-oil emulsion, Animals can be treated by administration methods such as spot-on treatment, pour-on treatment, spraying, bathing, washing, grinding, and spraying. A preferred method of administration of the composition of the present invention is spot-on treatment or pour-on treatment. The spot-on treatment is usually a method in which a liquid preparation is dropped or applied to one or several places on the skin of the host animal's head or back of the shoulder ribs. The pour-on treatment is usually the back of the host animal body. It is a method of pouring a liquid preparation along a line.
The spot-on process and the pour-on process are administration methods that are preferably used for controlling ectoparasites of animals that are kept as domestic animals or pets. The preparation used in this method can exert its efficacy by local administration of a chemical solution, but is required to have properties such that the active ingredient does not precipitate under low temperature conditions from the viewpoint of storage.
The composition of the present invention in the form of a liquid has preferable properties as a preparation used for spot-on treatment and pour-on treatment.

  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 usually the total of the present compound, octyl acetate and a co-solvent per 1 kg of living weight of the target animal. The amount is 1 to 5000 mg, preferably 10 to 1000 mg, more preferably 50 to 200 mg.

The composition of the present invention is preferably used as a skin external preparation for thermostat animals kept as livestock or pets.
The composition of the present invention may contain components other than the present compound, octyl acetate and a co-solvent. Examples of the components contained include surfactants, silicone oils, solid carriers, antioxidants, colorants, and light stability. Auxiliaries such as adhesives and pressure-sensitive adhesives.

Nonionic surfactants include nonionic surfactants, amphoteric surfactants, anionic surfactants and cationic surfactants. Nonionic surfactants include sorbitan stearate, sorbitan oleate, glyceryl stearate, glyceryl isostearate, glyceryl oleate, polyglyceryl stearate, polyglyceryl isostearate, polyglyceryl oleate, polyoxyethylene lauryl ether, polyoxyethylene Cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene styryl phenyl ether, coconut oil fatty acid polyoxyethylene sorbitan, oleic acid polyoxyethylene sorbitan, stearic acid polyoxyethylene sorbitan, tetraoleic acid polyoxyethylene Sorbit, polyoxyethylene hydrogenated castor oil, alkylphenol polyglycol ether And the like. Examples of amphoteric surfactants include lauryl betaine, stearyl betaine, di-sodium N-lauryl-p-iminodipropionate, and lecithin. Anionic surfactants include sodium lauryl sulfate, lauryl sulfate triethanolamine, polyoxyethylene lauryl ether sulfate sodium, polyoxyethylene lauryl ether sulfate triethanolamine, sodium dodecylbenzenesulfonate, dipolyoxyethylene lauryl ether phosphate Examples thereof include sodium and sodium dipolyoxyethylene oleyl ether phosphate. Examples of the cationic surfactant include cetyltrimethylammonium chloride and distearyldimethylammonium chloride.
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 the solid carrier 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.), chemical fertilizers (ammonium sulfate, phosphoric acid, ammonium nitrate, ammonium sulfate, urea, etc.), etc., fine powders and granules, 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-methyl methacrylate copolymers Ethylene-methacrylic acid ester copolymers such as ethylene-ethyl methacrylate copolymer; ethylene-acrylic acid ester copolymers such as ethylene-methyl acrylate copolymer, ethylene-ethyl acrylate copolymer; Ethylene-vinylcarboxylic acid copolymer such as acrylic acid copolymer; ethylene-tetracyclododecene copolymer; polypropylene resin such as propylene homopolymer, propylene-ethylene copolymer; poly-4-methylpentene- 1, polybutene-1, polybutadiene, polystyrene; acrylonitrile-styrene resin; styrene-based elastomer such as acrylonitrile-butadiene-styrene resin, styrene-conjugated diene block copolymer, hydrogenated styrene-conjugated diene block copolymer; fluorine resin ; Polymethacrylic Acrylic resins such as methyl acid; Polyamide resins such as nylon 6 and nylon 66; Polyester resins such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, polycyclohexylene dimethylene terephthalate; Polycarbonate, polyacetal, polyacryl Porous resin such as sulfone, polyacrylate, hydroxybenzoic acid polyester, polyetherimide, polyester carbonate, polyphenylene ether resin, polyvinyl chloride, polyvinylidene chloride, polyurethane, polyvinyl pyrrolidone, foamed polyurethane, foamed polypropylene, foamed ethylene), Felt, fiber, cloth, knitted fabric, sheet, paper, yarn, consisting of one or more of sugars, celluloses, glass, metal, ceramics, etc. Foam, and a porous body and a multifilament.

Antioxidants that can be contained in the composition of the present invention include ascorbic acid and salts thereof, citric acid and salts thereof, malic acid and salts thereof, tocopherol, soybean lecithin, cysteine hydrochloride, dibutylhydroxytoluene, butylhydroxyanisole, 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, and the like, 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 Compounds, macrocyclic lactone compounds, isoxazoline compounds, oxadiazine compounds, formamidine compounds, benzoylurea compounds, and the like, for example.
Examples of pyrethroid compounds include metfurthrin, fenpropraslin, 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, etiofen carb, fenobucarb, phenothiocarb, phenoxycarb, furthiocarb, isoprocarb, metorcarb, mesomil, oxathiocarb, NAC, Examples include pyrimicarb, propoxyl, XMC, thiodicarb, xylylcarb, and aldicarb.
Examples of the macrocyclic lactone (macrolide) -based compound include avermectin, milbemycin, ivermectin, doramectin, moxidectin, selamectin, emamectin, and aprinomectin (eprinomectin). eprinomectin), milbemectin, abamectin, lepimectin, milbemycin oxime, nemadectin, spinosad, spinetoram and the like.
Examples of isoxazoline compounds include afoxolaner and fluralaner.
Examples of the oxadiazine compound include indoxacarb.
Examples of the formamidine-based compound include amitraz.
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, 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-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 formulation examples and test examples, but the present invention is not limited to these examples.
First, formulation examples of the composition of the present invention are shown. In the examples, unless otherwise specified, parts means parts by weight. Hereinafter, dibutylhydroxytoluene is referred to as BHT, and butylhydroxyanisole is referred to as BHA.

Formulation Example 1
This compound 15g and octyl acetate 85g are mixed uniformly, and a liquid agent is obtained.
Formulation Example 2
Octyl acetate was added to 15 g of this compound so as to be 100 mL at 25 ° C., and mixed uniformly to obtain a liquid.

Formulation Example 3
20 g of this compound, 2 g of pyriproxyfen, 50 g of octyl acetate and 28 g of N-methyl-2-pyrrolidone were uniformly mixed to obtain a liquid.
Formulation Example 4
N-methyl-2-pyrrolidone was added to 20 g of this compound, 2 g of pyriproxyfen, and 50 g of octyl acetate so as to be 100 mL at 25 ° C. and mixed uniformly to obtain a liquid.

Formulation Example 5
20 g of this compound, 2 g of pyriproxyfen, 50 g of octyl acetate and 28 g of propylene carbonate were uniformly mixed to obtain a liquid.
Formulation Example 6
Propylene carbonate was added to 20 g of this compound, 2 g of pyriproxyfen, and 50 g of octyl acetate so as to be 100 mL at 25 ° C. and mixed uniformly to obtain a liquid.

Formulation Example 7
20 g of the present compound, 2 g of pyriproxyfen, 0.1 g of BHT, 50 g of octyl acetate and 27.9 g of N-methyl-2-pyrrolidone are uniformly mixed to obtain a solution.
Formulation Example 8
N-methyl-2-pyrrolidone is added to 20 g of the present compound, 2 g of pyriproxyfen, 0.1 g of BHT and 50 g of octyl acetate so as to be 100 mL at 25 ° C., and mixed uniformly to obtain a solution.

Formulation Example 9
20 g of the present compound, 2 g of pyriproxyfen, 0.1 g of BHT, 50 g of octyl acetate and 27.9 g of propylene carbonate are mixed uniformly to obtain a solution.
Formulation Example 10
Propylene carbonate is added to 20 g of the present compound, 2 g of pyriproxyfen, 0.1 g of BHT and 30 g of octyl acetate so as to be 100 mL at 25 ° C., and mixed uniformly to obtain a liquid.

Formulation Example 11
20 g of this compound, 2 g of pyriproxyfen, 0.1 g of BHT, 0.05 g of BHA, 50 g of octyl acetate and 27.85 g of N-methyl-2-pyrrolidone are uniformly mixed to obtain a solution.
Formulation Example 12
N-methyl-2-pyrrolidone is added to 20 g of the present compound, 2 g of pyriproxyfen, 0.05 g of BHT, 0.05 g of BHA, and 50 g of octyl acetate so as to be 100 mL at 25 ° C. and mixed uniformly to obtain a solution.

Formulation Example 13
20 g of this compound, 2 g of pyriproxyfen, 0.1 g of BHT, 0.05 g of BHA, 50 g of octyl acetate and 27.85 g of propylene carbonate are uniformly mixed to obtain a solution.
Formulation Example 14
Propylene carbonate is added to 20 g of this compound, 2 g of pyriproxyfen, BHT 0.1 g, BHA 0.05 g, and octyl acetate 50 g so as to be 100 mL at 25 ° C., and mixed uniformly to obtain a liquid agent.

Formulation Example 15
20 g of this compound, 2 g of pyriproxyfen, 0.2 g of ascorbic acid, 50 g of octyl acetate and 27.8 g of N-methyl-2-pyrrolidone are uniformly mixed to obtain a solution.
Formulation Example 16
N-methyl-2-pyrrolidone is added to 20 g of this compound, 2 g of pyriproxyfen, 0.2 g of ascorbic acid, and 50 g of octyl acetate so as to be 100 mL at 25 ° C., and mixed uniformly to obtain a solution.

Formulation Example 17
20 g of this compound, 2 g of pyriproxyfen, 0.2 g of ascorbic acid, 50 g of octyl acetate and 27.8 g of propylene carbonate are uniformly mixed to obtain a liquid preparation.
Formulation Example 18
Propylene carbonate is added to 20 g of this compound, 2 g of pyriproxyfen, 0.2 g of ascorbic acid and 50 g of octyl acetate so as to be 100 mL at 25 ° C., and mixed uniformly to obtain a liquid.

Formulation Example 19
20 g of this compound, 2 g of pyriproxyfen, 1 g of anhydrous citric acid, 50 g of octyl acetate and 27 g of N-methyl-2-pyrrolidone are uniformly mixed to obtain a solution.
Formulation Example 20
N-methyl-2-pyrrolidone is added to 20 g of this compound, 2 g of pyriproxyfen, 1 g of anhydrous citric acid, and 50 g of octyl acetate so as to be 100 mL at 25 ° C., and mixed uniformly to obtain a solution.

Formulation Example 21
20 g of this compound, 2 g of pyriproxyfen, 1 g of anhydrous citric acid, 50 g of octyl acetate and 27 g of propylene carbonate are uniformly mixed to obtain a solution.
Formulation Example 22
Propylene carbonate is added to 20 g of this compound, 2 g of pyriproxyfen, 1 g of anhydrous citric acid, and 50 g of octyl acetate so as to be 100 mL at 25 ° C., and mixed uniformly to obtain a solution.

Formulation Example 23
20 g of this compound, 2 g of pyriproxyfen, 1 g of malic acid, 50 g of octyl acetate and 27 g of N-methyl-2-pyrrolidone are uniformly mixed to obtain a solution.
Formulation Example 24
N-methyl-2-pyrrolidone is added to 20 g of this compound, 2 g of pyriproxyfen, 1 g of malic acid, and 50 g of octyl acetate so as to be 100 mL at 25 ° C., and mixed uniformly to obtain a solution.

Formulation Example 25
20 g of this compound, 2 g of pyriproxyfen, 1 g of malic acid, 50 g of octyl acetate and 27 g of propylene carbonate are uniformly mixed to obtain a solution.
Formulation Example 26
Propylene carbonate is added to 20 g of this compound, 2 g of pyriproxyfen, 1 g of malic acid, and 50 g of octyl acetate so as to be 100 mL at 25 ° C., and mixed uniformly to obtain a solution.

Formulation Example 27
20 g of this compound, 2 g of pyriproxyfen, BHT 0.1 g, BHA 0.05 g, ascorbic acid 0.2 g, octyl acetate 50 g and N-methyl-2-pyrrolidone 27.65 g are uniformly mixed to obtain a liquid.
Formulation Example 28
N-methyl-2-pyrrolidone is added to 20 g of this compound, 2 g of pyriproxyfen, BHT 0.1 g, BHA 0.05 g, ascorbic acid 0.2 g and octyl acetate 50 g so as to be 100 mL at 25 ° C., and mixed uniformly. To obtain a solution.

Formulation Example 29
20 g of this compound, 2 g of pyriproxyfen, BHT 0.1 g, BHA 0.05 g, ascorbic acid 0.2 g, octyl acetate 50 g and propylene carbonate 27.65 g are uniformly mixed to obtain a solution.
Formulation Example 30
Propylene carbonate is added to 20 g of this compound, 2 g of pyriproxyfen, BHT 0.1 g, BHA 0.05 g, ascorbic acid 0.2 g, and octyl acetate 50 g to 100 mL at 25 ° C., and mixed uniformly to obtain a solution. .

Formulation Example 31
20 g of this compound, 2 g of pyriproxyfen, BHT 0.1 g, BHA 0.05 g, anhydrous citric acid 1 g, octyl acetate 50 g and N-methyl-2-pyrrolidone 26.85 g are uniformly mixed to obtain a solution.
Formulation Example 32
N-methyl-2-pyrrolidone is added to 20 g of this compound, 2 g of pyriproxyfen, 0.05 g of BHT, 0.05 g of BHA, 1 g of anhydrous citric acid and 50 g of octyl acetate so that the volume becomes 100 mL at 25 ° C., and mixed uniformly. Get a solution.

Formulation Example 33
20 g of this compound, 2 g of pyriproxyfen, BHT 0.1 g, BHA 0.05 g, anhydrous citric acid 1 g, octyl acetate 50 g and propylene carbonate 26.85 g are uniformly mixed to obtain a solution.
Formulation Example 34
Propylene carbonate was added to 20 g of this compound, 2 g of pyriproxyfen, BHT 0.1 g, BHA 0.05 g, anhydrous citric acid 1 g 0.2 g, and octyl acetate 50 g so as to be 100 mL at 25 ° C., and mixed uniformly. obtain.

Formulation Example 35
20 g of this compound, 2 g of pyriproxyfen, BHT 0.1 g, BHA 0.05 g, malic acid 1 g, octyl acetate 50 g and N-methyl-2-pyrrolidone 26.85 g are uniformly mixed to obtain a solution.
Formulation Example 36
N-methyl-2-pyrrolidone was added to 20 g of this compound, 2 g of pyriproxyfen, 0.05 g of BHT, 0.05 g of BHA, 1 g of malic acid and 50 g of octyl acetate so that the volume was 100 mL at 25 ° C., and mixed uniformly. Obtain a solution.

Formulation Example 37
20 g of this compound, 2 g of pyriproxyfen, BHT 0.1 g, BHA 0.05 g, malic acid 1 g, octyl acetate 50 g and propylene carbonate 26.85 g are uniformly mixed to obtain a solution.
Formulation Example 38
Propylene carbonate is added to 20 g of this compound, 2 g of pyriproxyfen, BHT 0.1 g, BHA 0.05 g, malic acid 1 g 0.2 g, octyl acetate 50 g to 100 mL at 25 ° C., and mixed uniformly to obtain a solution. .

Next, it is shown as a test example that the composition of the present invention has an excellent control effect against ectoparasites.
In the following test examples, octyl acetate is abbreviated as OAc, ethyl acetoacetate as EAA, N-methyl-2-pyrrolidone as NMP, propylene carbonate as PC, and benzyl alcohol as BA.

Test Example 1: Drop administration test for mouse parasitic cat flea (Ctenocephalides felis) To a mixture of 20 g of this compound, 2 g of pyriproxyfen and 1 g of anhydrous citric acid, a mixed solvent having a weight ratio shown in Table 1 was added at 25 ° C. The composition of the present invention was prepared with a constant volume of 100 mL.
The prepared composition of the present invention was applied to a mouse at a dose of 0.1 ml per mouse body weight (kg), and the three coats of the back of the neck, the center of the back and the ridge were scraped and directly administered onto the skin. The day after the instillation, 20 fleas (cat flea adults) were released to the mice.
On the first day after the fleas were released, the number of surviving fleas infested with the mice was observed.

The extermination rate was calculated by the following calculation formula. When the extermination rate was 70% or more, it was determined as A, when 50 to 69%, B, and when 49% or less, C. The results are shown in Table 1.
Control rate (%) = (1−number of surviving flea parasites / number of flea worms) × 100

Test Example 2: Stability test under low temperature conditions To a mixture of 20 g of this compound, 2 g of pyriproxyfen and 1 g of anhydrous citric acid, a mixed solvent having a weight ratio shown in Table 2 was added under 25 ° C. conditions, and the volume was adjusted to 100 mL. Thus, the composition of the present invention was prepared.
The prepared composition of the present invention was stored at −5 ° C. for 2 weeks, and the presence or absence of solid precipitation was evaluated. The presence or absence of precipitation is shown in Table 2.

  The composition of the present invention is useful because it has excellent performance as a skin external preparation for controlling ectoparasites that parasitize constant temperature animals bred as domestic animals and pets.

Claims (13)

Formula (I)

An ectoparasite control composition comprising a nitrile compound represented by the formula: and octyl acetate. The ectoparasite control composition according to claim 1, wherein the weight ratio of the nitrile compound represented by formula (I) to octyl acetate is in the range of 1: 0.5 to 1:10. The ectoparasite control composition according to claim 1, wherein the weight ratio of the nitrile compound represented by formula (I) to octyl acetate is in the range of 1: 1 to 1: 5. The ectoparasite control composition according to any one of claims 1 to 3, wherein the octyl acetate content in the ectoparasite control composition is 10 to 80% by weight. The ectoparasite control composition according to any one of claims 1 to 3, wherein the content of octyl acetate relative to the ectoparasite control composition is 20 to 60% by weight. The ectoparasite control composition according to any one of claims 1 to 5, wherein the ectoparasite control composition is in the form of a solution. The ectoparasite control composition according to any one of claims 1 to 6, further comprising a solvent having a solubility of the nitrile compound represented by the formula (1) at 25 ° C of 40% by weight or more. The ectoparasite control according to claim 7, wherein the content of the nitrile compound represented by formula (1) having a solubility at 25 ° C of 40% by weight or more with respect to the ectoparasite control composition is 5 to 90% by weight. Composition. The ectoparasite control according to claim 7, wherein the content of the nitrile compound represented by formula (1) having a solubility at 25 ° C of 40% by weight or more with respect to the ectoparasite control composition is 10 to 65% by weight. Composition. A solvent in which the solubility of the nitrile compound represented by the formula (1) at 25 ° C. is 40% by weight or more is N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, propylene glycol monomethyl ether, acetophenone, methyl acetoacetate The ectoparasite control composition according to any one of claims 1 to 7, which is at least one solvent selected from the group consisting of ethyl acetoacetate, γ-butyrolactone, dimethyl sulfoxide and propylene carbonate. The solvent having a solubility of the nitrile compound represented by the formula (1) at 25 ° C. of 40% by weight or more is at least one solvent selected from the group consisting of N-methyl-2-pyrrolidone, ethyl acetoacetate and propylene carbonate. The ectoparasite control composition according to any one of claims 1 to 7. The ectoparasite control composition according to any one of claims 1 to 11, wherein the ectoparasite to be controlled is a flea, lice or mite pest. A method for controlling ectoparasites, comprising administering an effective amount of the ectoparasite control composition according to any one of claims 1 to 12 to an animal.