JP2000044412A - Insect-proofing agent for clothes - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an insect-proofing agent for clothes, manifesting excellent activities against pest of clothes, excellent in both immediate activities and residual activities, and hardly causing bad effects such as bad smell and discoloration on the clothes by including a specific compound as an active ingredient. SOLUTION: The objective insect-proofing agent contains (A) 2,3,5,6- tetrafluoro-4-methylbenzyl 3-(2-chloro-2-fluorovinyl)-2,2- dimethylcyclopropanecarboxylate as an active ingredient. The component A can be used in the insect-proofing agent as it is, but the component A is preferably used by preparing a solid form such as a powder and a tablet, a liquid form such as emulsion and aerosol, a cold transpiring agent such as the transpiring agent of impregnated paper, or the like by adding a proper carrier, and optionally a surfactant and other adjuvant for preparation, to the component A. The content of the component A is preferably 0.01-80 wt.%, and the insect- proofing agent is preferably used so that the proportion of the component A may be 10 mg-100 g/m2.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an insect repellent for clothing.

[0002]

2. Description of the Related Art Pyrethroid compounds have been widely used as domestic insecticides effective against sanitary pests such as flies and mosquitoes. D-arlesrin and praletrin having a norone ring are used as active ingredients for mosquito coils and mats. However, these compounds are not necessarily sufficient in terms of efficacy as an insect repellent for clothing.

[0003]

Under these circumstances, the present inventors have conducted various studies and found that 2,3,5,6-tetrafluoro-4-methylbenzyl 3- (2-chloro-2-fluoro Insect repellents using (vinyl) -2,2-dimethylcyclopropanecarboxylate show excellent effects against clothing pests and are not only excellent in immediate action and residual effect, but also have an adverse effect such as unpleasant odor and discoloration on clothing. The present invention was found to exhibit excellent performance as an insect repellent for clothing, for example, to prevent the occurrence thereof. That is, the present invention relates to 2,3,5,6-tetrafluoro-4-methylbenzyl 3- (2-chloro-2-fluorovinyl) -2,2-dimethylcyclopropanecarboxylate (hereinafter referred to as the present invention). Abbreviated as a compound) as an active ingredient.

[0004]

BEST MODE FOR CARRYING OUT THE INVENTION Examples of clothing pests that can be controlled by the insecticide for clothing of the present invention include, for example, Tinea genus Tinea translucens (Iga) and the like Tineola genus Tineola bisselliella (koiga, common clothes moth) and the like Hofmannophila pseudospretella (brown house) moth), etc. Lepidopteran clothing pests, such as Endrosis genus Endrosis sarcitrella (white-shouldered house moth), etc. Attagenus genus Attagenus unicolor, etc. Dermestes (hide beetles) D. maculatus (hide beetles) D. lardarius (larder beetle) D. haemorrhoidalis D. peruvianus and other insect pests of the order Coleoptera.

The compound according to the present invention is disclosed, for example, in
It can be produced according to the method described in JP-A-225442.

[0006] The insect repellent for clothing of the present invention is generally used for storing clothing or clothing such as a Japanese chest, a clothes chest, a rearranging chest, a garment box, a closet, etc. where insect repellent effects on clothing are required. Used in the various storage tools used.

Although the compound of the present invention can be used as it is as the insect repellent for clothing of the present invention, usually, the compound of the present invention comprises a solid carrier, a sublimable carrier, a liquid carrier,
A suitable carrier such as a gaseous carrier and, if necessary, a surfactant,
Addition of other pharmaceutical auxiliaries, for example, solid forms such as powders, granules, tablets, rod-shaped preparations and plate-shaped preparations, or wettable powders, emulsions, dispersants, suspensions, sprays, aerosols It is used as an insect repellent for clothing in the form of a liquid agent such as an agent or an oil agent, or a non-heated evaporant such as a resin evaporant or an impregnated paper evaporant.

The carrier (diluent) used in preparing the above liquid form includes, for example, water, alcohols such as methyl alcohol and ethyl alcohol, ethyl acetate, and the like.
Esters such as butyl acetate, dichloromethane, dichloroethane, trichloroethane, halogen hydrocarbons such as carbon tetrachloride, acetone, ketones such as methyl ethyl ketone, ethers such as tetrahydrofuran and dioxane,
Aliphatic hydrocarbons such as hexane, kerosene, paraffin, petroleum benzine, cyclohexane, kerosene, gas oil, nitriles (acetonitrile, isobutyronitrile, etc.),
Ters (diisopropyl ether, dioxane, etc.), acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, etc., dimethyl sulfoxide, Vegetable oils such as soybean oil and cottonseed oil can be mentioned.

[0009] Examples of auxiliary agents for pharmaceutical preparations that can be used in the liquid form include surfactants such as emulsifiers and dispersants, spreading agents, wetting agents, stabilizers, propellants, and film-forming agents. Specifically, for example, soaps, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene alkyl aryl ethers such as polyoxyethylene nonylphenyl ether, polyethylene glycol monostearate and the like Polyoxyethylene fatty acid esters, polyoxyethylene glycerin fatty acid esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, higher alcohol sulfates, alkylaryl sulfonates such as dodecylbenzene sulfonate, alkyl sulfates salt, Surfactants such as alkyl sulfonate, alkyl phosphate, alkyl aryl ether phosphate; gaseous carriers such as liquefied petroleum gas (LPG), dimethyl ether, fluorocarbon, butane gas, carbon dioxide gas, ie, propellant; Cellulose derivatives such as acetylcellulose, methylcellulose and acetylbutylcellulose, vinyl resins such as vinyl acetate resin, alkyd resins, urea resins, epoxy resins, polyester resins, urethane resins, silicone resins, acrylic resins, Rubber such as chlorinated rubber, film-forming agent such as polyvinyl alcohol; casein, gelatin, alginic acid, starch, gum arabic, cellulose derivatives, polysaccharides such as alginic acid, carboxymethyl cellulose (CMC), lignin derivatives, bentonite Sugars,
Auxiliary agents for preparations such as fixing agents and dispersants such as synthetic water-soluble polymers such as polyvinyl alcohol, polyvinylpyrrolidone and polyacrylic acids can be exemplified.

[0010] The carrier used for preparing the above-mentioned solid form includes, for example, clays such as silicic acid, kaolin, activated carbon, bentonite, diatomaceous earth, talc, clay, calcium carbonate, synthetic hydrous silicon oxide, and acid clay. , Ceramics, sericite, quartz, sulfur, hydrated silica and other inorganic minerals, fine powders and granular materials such as ammonium sulfate, phosphorous ammonium, ammonium nitrate, urea, and salt ammonium and other various minerals such as ceramic powder Examples thereof include a substance powder and an inclusion compound such as cyclodextrin. Sublimable carriers include, for example, 2,4,6-triisopropyl-1,3,5-trioxane, tricyclo [5,5,1,0] decane, acetone oxime, amylcarbamate, butylcarbamate, parabutyraldehyde , Chloroacetanilide, 4-chloro-3-methylphenol, cyclohexanone oxime, diacetamide, dihydroxyhexane, dimethyloxale
Dimethylquinone, furfural oxime, paradichlorobenzene, naphthalene, camphor and the like.

Further, the compound according to the present invention is kneaded with a resin such as a synthetic resin such as polyethylene, polypropylene, nylon, polyvinyl chloride, polyvinylidene chloride, polyester or the like in the solid form. The form of a resin molded product obtained by molding is also included.

The insecticide for clothing of the present invention having various forms thus prepared contains the compound of the present invention in an amount of usually 0.01 to 80% by weight, preferably 0.1 to 6% by weight.
It is contained in the range of 5% by weight.

Further, the insect repellent for clothing of the present invention comprises piperonyl butoxide (α- [2- (2-butoxyethoxy) ethoxy] -4,5) which can be added to a known pyrethroid insecticide if necessary. -Methylenedioxy-2-propyltoluene), MGK-264 (N- (2-ethylhexyl) bicyclo [2.2.1] hept-5-ene-2,3
-Dicarboximide), S-421 (bis- (2,
(3,3,3-tetrachloropropyl) ether), and as a stabilizer, for example, an organic acid, PAP (acidic isopropyl phosphate), BHT (2,6-di-tert-).
Butyl-4-methylphenol), BHA (2-ter
t-butyl-4-methoxyphenol and 3-tert-
Butyl-4-methoxyphenol), vegetable oils, mineral oils, surfactants, fatty acids or esters thereof, and the like. These addition amounts are usually 1/1 to the compound of the present invention.
It is 00 to 10 times by weight. Further, as other additives, for example, paraben (parahydroxybenzoic acid), PC
Antibacterial and antifungal agents such as antibacterial agents of natural extracts such as MX (4-chloro-3,5-dimethylphenol), thymol (6-isopropyl-m-cresol) and hinokitiol can also be used. Furthermore, the insect repellent for clothing of the present invention may contain an active ingredient of another insect repellent for clothing. Further, the insect repellent for clothing of the present invention can be used in combination with another insect repellent for clothing.

The preparation thus obtained is used as it is or after dilution with water or the like. It can also be mixed with or used in combination with other insecticides, miticides, fungicides, insect repellents, ultraviolet absorbers, and other additives such as fragrances, pigments, and pigments. Examples of such insecticides and acaricides include fenitrothion [O, O-dimethyl O- (3-methyl-4-nitrophenyl) phosphorothioate] and fenthion [O, O-dimethyl O- (3-methyl- 4
-(Methylthio) phenyl) phosphorothioate], diazinon [O, O-diethyl-O-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate-
G), chloropyrifos [O, O-diethyl-O-3,
5,6-trichloro-2-pyridyl phosphorothioe-
Acetoate [O, S-dimethylacetylphosphoramide thioate], methidathion [S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3] -Ylmethyl O, O-dimethyl phosphorodithioate], disulfotone [O, O-diethyl S
-2-ethylthioethyl phosphorodithioate], DD
VP [2,2-dichlorovinyldimethylphospho-
G), sulprophos [O-ethyl O-4- (methylthio) phenyl S-propyl phosphorodithioate],
Cyanophos [O-4-cyanophenyl O, O-dimethyl phosphorothioate], dioxabenzophos [2-methoxy-4H-1,3,2-benzodioxaphosphorin-2-sulfide], dimethoate [O, O-dimethyl-S- (N-methylcarbamoylmethyl) dithiophosphate], fentoate [ethyl 2-dimethoxyphosphinothioylthio (phenyl) acetate], malathion [diethyl (dimethoxyphosphino) Thioylthio) succinate], trichlorfon [dimethyl 2,2
2,2-trichloro-1-hydroxyethylphosphone-
G], azinphosmethyl [S-3,4-dihydro-4-
Oxo-1,2,3-benzotriazin-3-ylmethyl O, O-dimethylphosphorodithioate], monocrotophos [dimethyl (E) -1-methyl-2- (methylcarbamoyl) vinyl phosphate], Ethion [O,
Organic phosphorus compounds such as O, O ', O'-tetraethyl S, S'-methylenebis (phosphorodithioate)], B
PMC (2-sec-butylphenylmethylcarbamine
G), benfracarb [ethyl N- [2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl (methyl) aminothio] -N-isopropyl-
β-alaninate], propoxur [2-isopropoxyphenyl N-methylcarbamate], carbosulfan [2,3-dihydro-2,2-dimethyl-7-benzo [b] furanyl N-dibutylamino Thio-N-methylcarbamate], carbaryl [1-naphthyl-N-methylcarbamate], mesomil [S-methyl-N-
[(Methylcarbamoyl) oxy] thioacetimide
G], Ethiophenecarb [2- (ethylthiomethyl)
Phenylmethylcarbamate], aldicarb [2-methyl-2- (methylthio) propionaldehyde O-
Methylcarbamoyl oxime], oxamyl [N, N-
Dimethyl-2-methylcarbamoyloxyimino-2-
(Methylthio) acetamide], phenothiocarb [S-
Carbamate compounds such as 4-phenoxybutyl) -N, N-dimethylthiocarbamate; empentrin [(RS) -1-ethynyl-2-methyl-2-pentenyl (1R) -cis, trans- Chrisante Mart),
1-ethynyl-2-fluoro-2-pentenyl-d-tr
ans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate, transfluthrin [2,3,5,6-tetrafluorobenzyl (1R
-Trans) -3- (2,2-dichlorovinyl) -2,
2-dimethylcyclopropanecarboxylate], tetraretrin (RS) -3-allyl-2-methyl-4-oxocyclopent-2-enyl 2,2,3,3-tetramethylcyclopropanecarboxylate, 5- (2-
Propynyl) furfuryl 2,2,3,3-tetramethylcyclopropanecarboxylate, etofenprox [2- (4-ethoxyphenyl) -2-methylpropyl-3-phenoxybenzyl ether], fenvalerate [( RS) -α-cyano-3-phenoxybenzyl (RS) -2- (4-chlorophenyl) -3-methylbutyrate], esfenvalerate [(S) -α-cyano-3-phenoxybenzyl (S ) -2- (4-Chlorophenyl) -3-methylbutyrate], fenpropatrin [(RS) -α-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate] , Cypermethrin [(RS) -α-cyano-
3-phenoxybenzyl (1RS) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], permethrin [3
-Phenoxybenzyl (1RS) -cis, trans-
3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], cyhalothrin [(R
S) -α-cyano-3-phenoxybenzyl (Z)-
(1RS) -cis-3- (2-chloro-3,3,3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate], deltamethrin [(S) -α-cyano -3-phenoxybenzyl (1
R) -cis-3 (2,2-dibromovinyl) -2,2-
Dimethylcyclopropanecarboxylate], cycloprothrin [(RS) -α-cyano-3-phenoxybenzyl (RS) -2,2-dichloro-1- (4-ethoxyphenyl) cyclopropanecarboxylate] , Fluvalinate (α-cyano-3-phenoxybenzyl N
-(2-chloro-α, α, α-trifluoro-p-tolyl) -D-variate), bifensulin (2-methylbiphenyl-3-ylmethyl) (Z)-(1RS) -ci
s-3- (2-Chloro-3,3,3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate, 2-methyl-2- (4-bromodifluoromethoxyphenyl) Propyl (3-phenoxybenzyl) ether, tralomethrin [(1R-cis) 3
{(1′RS) (1 ′, 2 ′, 2 ′, 2′-tetrabromoethyl)}-2,2-dimethylcyclopropanecarboxylic acid (S) -α-cyano-3-phenoxybenzyl ester], silafluofen [4-ethoxyphenyl} 3
-(4-fluoro-3-phenoxyphenyl) propyl @ dimethylsilane], d-phenothrin [3-phenoxybenzyl (1R-cis, trans) -chrysanthemate], cyphenothrin [(RS) -α-cyano-3
-Phenoxybenzyl (1R-cis, trans) -chrysanthemate], d-resmethrin [5-benzyl-
3-furylmethyl (1R-cis, trans) -chrysanthemate], acrinasulin [(S) -α-cyano-3
-Phenoxybenzyl (1R-cis (Z))-(2,
2-dimethyl-3- {3-oxo-3- (1,1,1,1
3,3,3-hexafluoropropyloxy) propenyl {cyclopropanecarboxylate], cyfluthrin [(RS) -α-cyano-4-fluoro-3-phenoxybenzyl 3- (2,2-dichlorovinyl)- 2,2
-Dimethylcyclopropanecarboxylate], tefluthrin [2,3,5,6-tetrafluoro-4-methylbenzyl (1RS-cis (Z))-3- (2-chloro-
3,3,3-trifluoroprop-1-enyl) -2,
2-dimethylcyclopropanecarboxylate], tetramethrin [3,4,5,6-tetrahydrophthalimidomethyl (1RS) -cis, trans-chrysanthemate], aletrin [(RS) -3-allyl-2-methyl -4-oxocyclopent-2-enyl (1RS)-
Cis, trans-chrysanthemate], praletrin [(S) -2-methyl-4-oxo-3- (2-propynyl) cyclopent-2-enyl (1R) -cis, trans-chrysanthemate], imiprosulin [ 2,5-
Dioxo-3- (prop-2-ynyl) imidazolidin-1-ylmethyl (1R) -cis, trans-2,2
-Dimethyl-3- (2-methylprop-1-enyl) cyclopropanecarboxylate], d-framethrin [5- (2-propynyl) furfuryl (1R) -cis,
Pyrethroid compounds such as trans-chrysanthemate] and buprofezin (2-tert-butylimino-3).
Derivatives such as -isopropyl-5-phenyl-1,3,5-thiadiazinan-4-one), nitroimidazolidine derivatives, cartap (S, S '-(2-dimethylaminotrimethylene) bis (thiocarbamate)
G), thiocyclam [N, N-dimethyl-1,2,3
N-cyano-N'-methyl-N ', such as -trithiane-5-ylamine] and bensultap [S, S'-2-dimethylaminotrimethylene di (benzenethiosulfonate)]. N-cyanoamidine derivatives such as-(6-chloro-3-pyridylmethyl) acetamidine; endosulfan [6,7,8,9,
10,10-hexachloro-1,5,5a, 6,9,9
a-hexahydro-6,9-methano-2,4,3-benzodioxathiepine oxide], γ-BHC (1,
2,3,4,5,6-hexachlorocyclohexane],
Chlorinated hydrocarbon compounds such as 1,1-bis (chlorophenyl) -2,2,2-trichloroethanol, chlorofluazurone [1- (3,5-dichloro-4- (3-chloro-5- Trifluoromethylpyridin-2-yloxy)
Phenyl) -3- (2,6-difluorobenzoyl) urea], teflubenzuron [1- (3,5-dichloro-
2,4-difluorophenyl) -3- (2,6-difluorobenzoyl) urea], flufenoxuron [1-
Benzoylphenylurea-based compounds such as (4- (2-chloro-4-trifluoromethylphenoxy) -2-fluorophenyl] -3- (2,6-difluorobenzoyl) urea], amitraz [N, N '[( Methylimino)
Dimethylidin] di-2,4-xylysine], chlordimeform [N '-(4-chloro-2-methylphenyl)-
Formamidine derivatives such as N, N-dimethylmethinimidamide, diafenthiuron [N- (2,6-diisopropyl-4-phenoxyphenyl) -N'-tert-
Thiourea derivatives such as butylcarbodiimide], phenylpyrazole-based compounds, methoxadiazone [5-methoxy-3- (2-methoxyphenyl) -1,3,4-oxadiazol-2- (3H) -one], bromopropyl −
G [isopropyl 4,4'-dibromobenzylate
G), tetradiphone [4-chlorophenyl 2,4,5
-Trichlorophenylsulfone], quinomethionate [S, S-6-methylquinoxaline-2,3-diyldithiocarbonate], propargite [2- (4-te
rt-butylphenoxy) cyclohexyl prop-2
-Yl sulfite], fenbutatin oxide [bis [tris (2-methyl-2-phenylpropyl)]
Tin] oxide], hexthiazox [(4RS, 5
RS) -5- (4-Chlorophenyl) -N-chlorohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide], clofentezine [3,6-
Bis (2-chlorophenyl) -1,2,4,5-tetrazine], pyridaben [2-tert-butyl-5- (4
-Tert-butylbenzylthio) -4-chloropyridazin-3 (2H) -one], fenpyroximate [t
tert-butyl (E) -4-[(1,3-dimethyl-5
-Phenoxypyrazol-4-yl) methyleneaminooxymethyl] benzoate], debufenpyrad [N-
4-tert-butylbenzyl) -4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxamide],
Polynactin complex (tetranactin, dinactin, trinactin), pyrimidifene [5-chloro-
N- [2- {4- (2-ethoxyethyl) -2,3-dimethylphenoxy} ethyl] -6-ethylpyrimidine-
4-amine, milbemectin, abamectin, iva-mectin, azadirachtin [AZAD] and the like,

Examples of repellents include 3,4-caranediol, N, N-diethyl-m-toluamide, 2- (2
-Hydroxyethyl) -1-piperidinecarboxylic acid-1
-Methylpropyl, p-menthane-3,8-diol,
2,3,4,5, -bis ({2-butylene) tetrahydrofurfural, di-n-propyl isosine colonate, di-n-butyl succinate, 2-hydroxyoctyl sulfide, (N-carbo -Sec-butyroxy) -2-
(2′-hydroxyethyl) piperidin and hyssop oil, horseradish oil, bay oil, royal oil, fennel oil, basil oil, anisestar oil, shobu oil,
Oregano sandalwood oil, yarrow oil,
Perilla oil, valerian oil, ginger oil, palmarosa oil,
Pest repellents containing plant essential oils, such as eucalyptus oil, ylang-ylang oil and clove oil, as active ingredients are listed as active ingredients. Examples of antioxidants include butylhydroxyanisole, dibutylhydroxytoluene, and tocophero-
And γ-oryzanol.

The insect repellent for clothing of the present invention can be used in a place where an insect repellent effect is required for clothing, for example, in the storage furniture of clothing, suitable packaging materials, for example, various known brushed, crepe,
It can be used by a method of wrapping in a net-like or layered paper, non-woven fabric, cloth, or the like, or a method of putting in without packaging, or a method of spraying, spraying, coating, sticking, or the like. In particular, since the compound according to the present invention is substantially odorless, it can be used by a method of directly contacting clothing or clothing.

The insect repellent for clothing of the present invention may be applied to a suitable sheet-like substrate in advance, impregnated, sprayed, dropped,
By holding by kneading etc., in the form held by the substrate,
Can also be used. The sheet-like base material used in this case is a film, sheet, paper, cloth, nonwoven fabric, or the like of various materials.
It includes leather and the like, and as a material, for example, polyethylene, polypropylene, nylon, polyvinyl chloride,
Examples thereof include synthetic resins such as polyvinylidene chloride and polyester, animal fiber, inorganic fiber, and the like. And
As the sheet-like base material, not only a base material using a single material, but also a sheet or a blended fabric obtained by mixing two or more of these materials, a sheet obtained by laminating two or more of nonwoven fabrics of these materials, and the like. You can also mention. If necessary, an inorganic powder or the like can be contained in the sheet-like base material.

Further, storage furniture members, for example, wood such as drills, pencil ferns, cousin, yew, fir, todomatsu, tsuga, johncon, jielton, agathis, cedar, onigiri, beech, mizunara, zelkova, hargore, mizuna; Plastics such as vinyl resin, chlorinated polyethylene, polyethylene, polypropylene, and vinyl chloride-vinyl acetate copolymer; the present invention is applied to a cardboard or the like in advance, by impregnation, spraying, dropping, or, if possible, by kneading. An insect repellent for clothing can also be held. As the preferable holding means, the compound according to the present invention and a compound which gels or crystallizes or solidifies at room temperature liquefied by heating or the like, separately or in advance after mixing, under normal pressure, under reduced pressure or For example, a method of impregnating furniture members under pressure can be exemplified. Examples of the compound that can be liquefied by heating or the like and that gels at normal temperature used here include ordinary gelling agents, for example, dibenzylidene-D-sorbitol, and are crystallized at normal temperature that can be liquefied by heating or the like. Examples of the solidifying compound include acetanilide, dimethyl isophthalate, magnesium acetate, dimethyl terephthalate, maleic anhydride, lauric acid, stearyl alcohol, petroleum solid paraffin, animal and plant solid wax, sodium tetraborate (decahydrate) , Sodium aluminum sulfate, magnesium sulfate (hexahydrate), 2,4,6-triisopropyl-1,3,5-trioxane, tricyclodecane, trimethylenenorbornene, disodium hydrogenphosphate (pentahydrate). be able to.

The insect repellent for clothing of the present invention comprises the chemical compound according to the present invention.
Compound is usually 10mg-100g / m ^TwoUsed to be
Is done.

The insect repellent for clothing of the present invention not only has a strong insect repellent effect against clothing pests and a moderate volatility,
It has both immediate and residual effects. Further, when a dosage form such as a powder, a granule, or a sublimation preparation is used, it can be volatilized effectively in a small amount for short-term use. Furthermore, it is odorless with almost no unpleasant odor, it can be flavored as you like, and it does not cause discoloration of clothes or other adverse effects even when clothes such as clothes are stored for a long time in a container such as a closet. It has excellent performance such that it can be worn immediately after being put out.
Further, the compound according to the present invention is a compound having low toxicity to warm-blooded animals.

[0021]

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples.

Formulation Example 1 Single-sided polyethylene laminated nonwoven fabric (PE 80μ)
Thickness), the mixture of the compound of the present invention: butylhydroxyanisole = 5: 1 parts by weight was applied so that the compound of the present invention was 5 g / m ^2, and the polyethylene (80 μ thick) nonwoven fabric was further applied to the mixture. Heat sealing is performed to obtain a three-layer insect-proof sheet. Formulation Example 2 A solution obtained by dissolving the compound of the present invention in acetone was added to 0.1%
It is applied to 9 m ² toto paper at 2 g / m ² and dried to obtain an insect repellent sheet for the Japanese dance basin. Formulation Example 3 A solution of the compound of the present invention in acetone was added to 10
It is applied to a 0 mmφ × 3 mm pulp cardboard at a concentration of 3 mg / cm ² and dried to obtain a mat-like insect repellent sheet. Formulation Example 4 Compound according to the present invention: silicic acid: cyclododecane = 1:
1: 98 parts by weight were sufficiently ground and mixed, and then 300 kg / cm ²
A tablet is obtained by compressing under pressure to 10 g / tablet (this is suitable for packaging and use in a non-woven fabric). Formulation Example 5 A 10% dichloromethane solution containing the compound of the present invention containing 110% of the compound of the present invention was applied from the other side of a cardboard cardboard laminated with vinylidene chloride-coated nylon / polyethylene to a thickness of 20 μm on one side.
ml / m ² , and after distilling off the solvent, 500 × 800 × 20
Obtain an insect-proof costume box with a lid of 0 mm.

The compounds used for comparison in the following test examples are shown below. Comparative compound A

Embedded image Comparative compound B

Embedded image Comparative compound C

Embedded image

Test Example 1 A 2 cm × 2 cm wool muslin cloth and 10 middle larvae of kioiga were placed on the bottom of a polyethylene cup (diameter of bottom 10 cm, diameter of opening 12.5 cm, height 9.5 cm, volume 950 cm ³ ). Put it in, 2, 3, 5, 6
Tetrafluoro-4-methylbenzyl (1R) -trans-3- (2-chloro-2-fluorovinyl) -2,2
-Filter paper (2 cm × 2 cm) treated with a predetermined amount of dimethylcyclopropanecarboxylate (Compound 1 of the present invention) and Comparative Compounds A to C was suspended and sealed. After leaving it at a temperature of 25 ° C. for one week, it was opened, and the mortality of trophozoites was determined. Further, the degree of damage to the wool muslin cloth was examined. The criteria for determining the degree of damage were +++: markedly damaged ++: slightly damaged +: slightly damaged ±: slightly damaged-: no damage (2 repetitions). Table 1 shows the obtained results.

[0025]

[Table 1]

Test Example 2 A 2 cm × 2 cm wool muslin cloth and 10 middle larvae of koraiga were placed on the bottom of a polyethylene cup (diameter of bottom 10 cm, diameter of opening 12.5 cm, height 9.5 cm, volume 950 cm ³ ). Put it in, 2, 3, 5, 6
Tetrafluoro-4-methylbenzyl (1RS) -trans-3- (2-chloro-2-fluorovinyl) -2,
A filter paper (2 cm × 2 cm) treated with a predetermined amount of 2-dimethylcyclopropanecarboxylate (Compound 2 of the present invention) and comparative compounds B and C was suspended and sealed. Temperature 25 ° C
, And opened for one week, and the rate of trophozoites was determined. Further, the degree of damage to the wool muslin cloth was examined. The criteria for determining the degree of damage were +++: markedly damaged ++: slightly damaged +: slightly damaged ±: slightly damaged-: no damage (2 repetitions). Table 2 shows the obtained results.

[0027]

[Table 2] In Test Examples 1 and 2, the present compound 1 and the present compound 2 were observed immediately after the treatment and at the time of observation one week after the treatment.
No discoloration of the chemically treated filter paper was observed, and no off-flavor was observed.

Test Example 3 3.3 mg of the present compound 1 and the present compound 2 was dissolved in acetone, and the acetone solution was 2 cm × 1.5 cm.
And air-dried to prepare a chemical-treated filter paper. Brass powder treated filter paper [Brass powder (Cu / Zn = 76-78 / 22)
To 24) at a rate of about 0.03 mg / cm ² and a diameter of 5.5.
mm filter paper on one side] with the brass powder treated side inside, fold it into two pieces, insert the above-mentioned chemical-treated filter paper into it, clip it, and heat seal the whole into an aluminum laminate bag. Close and place in a thermostat at 60 ° C for 48 hours.
Hold for hours. Thereafter, the package was opened, and the discoloration and odor of the filter paper treated with brass powder and the filter paper treated with a chemical were examined. As a result, no odor or discoloration was observed in both the brass powder-treated filter paper and the chemical-treated filter paper.

Test Example 4 Ten adults of the knot moth were released into a polyethylene cup (diameter 9 cm, height 4.5 cm), and a 16-mesh nylon net was placed on top of the adult to prevent the insects from directly touching the drug-treated surface. The cup was placed upside down and placed on a 9 cm diameter aluminum dish treated with a predetermined amount of Compound 1 of the present invention and Comparative Compounds B and C. After 120 minutes at 25 ° C., the cup was removed from the aluminum dish, and the mortality after 24 hours was determined. Table 3 shows the obtained results.

[0030]

[Table 3]

Test Example 5 Insecticidal test on carp by volatilization at room temperature Vinyl rocker (60 cm × 50 cm × 155 cm)
After air-drying square filter paper (10 cm × 15 cm) treated with an acetone solution containing 125 mg of the present compound 1,
The clothes were hung together with six clothes to prepare a test device. Hanging a bag containing 8 to 10 middle larvae of kiga moth and one 2 cm × 2 cm ulmosulin cloth and a bag containing 10 to 15 kiga moga eggs, at a temperature of 25 ° C. and a humidity of 60%. saved. One week later, the number of surviving, writhing, and dead larvae of the middle-aged larvae of the larva was determined to determine the rate of mortal worms, and the degree of damage to the ulmosulin cloth was examined. In this test, the criteria for determining the degree of damage were +++: markedly damaged ++: slightly damaged +: slightly damaged ±: slightly damaged-: not damaged The number of surviving hatching larvae, the number of struggling hatching larvae, and the number of dead eggs were investigated, and the control rate was calculated by the following equation (1).

[Equation 1] Control rate (%) = (number of dead eggs + number of mortal hatching larvae) ÷
(Number of live hatching larvae + number of bitter hatching larvae + number of dead eggs) x 100 The vinyl rocker was preserved as it was, and the same test was repeated 2, 4, 8, 12, and 24 weeks after the test apparatus was prepared. The residual effect of the compound was investigated. The test was performed in exactly the same manner as above except that no active ingredient was contained. Table 4 shows the mortality of the middle larvae of the knot moth and the degree of harm of the ulmosulin cloth, which were installed in the test apparatus at a predetermined time,
Table 5 shows the control rates of knot moth eggs.

[0032]

[Table 4]

[0033]

[Table 5]

Test Example 6 Insecticidal test by cold volatilization of carp moth A filter paper (34 cm x 58 cm) treated with an acetone solution containing 100 mg of the compound of the present invention in a clothes box (427 mm x 725 mm x 158 mm) was air-dried and then put on clothes. And a test apparatus was prepared. A bag containing 8 to 10 middle larvae of kiga moth and one ulmosulin cloth of 2 cm × 2 cm and a bag containing 10 to 15 koi moga eggs were placed on the clothes, and the temperature was 25 ° C. and the humidity was 60%. Saved. One week later, the number of surviving, writhing, and dead larvae of the middle-aged larvae of the larva was determined to determine the rate of mortal worms, and the degree of damage to the ulmosulin cloth was examined. In this test, the criteria for determining the degree of damage were +++: markedly damaged ++: slightly damaged +: slightly damaged ±: slightly damaged-: not damaged The number of surviving hatching larvae, the number of struggling hatching larvae, and the number of dead eggs were investigated, and the control rate was calculated by the above formula (1). Keep the clothes box as it is, and prepare the test equipment for 2, 4, 8, 12, and 24
After a week, the same test was repeated to check the residual effect of the compound. The test was performed in exactly the same manner as above except that no active ingredient was contained. Table 6 shows the mortality of the middle-aged larvae of the knot moth and the degree of harm to the ulmosulin cloth, which were set in the test apparatus at a predetermined time, and Table 7 shows the control rate of the knot mottle eggs.

[0035]

[Table 6]

[0036]

[Table 7]

[0037]

EFFECT OF THE INVENTION The insect repellent of the present invention is not only effective against clothing pests but also excellent in immediate action and residual effect, and does not cause adverse effects such as unpleasant odor and discoloration on clothing. Demonstrates excellent performance as an insect repellent.

Claims (3)

[Claims] (1) 2,3,5,6-tetrafluoro-4-methylbenzyl 3- (2-chloro-2-fluorovinyl)
An insect repellent for clothing, comprising -2,2-dimethylcyclopropanecarboxylate as an active ingredient. 2. Effective use of 2,3,5,6-tetrafluoro-4-methylbenzyl (1RS) -trans-3- (2-chloro-2-fluorovinyl) -2,2-dimethylcyclopropanecarboxylate. An insect repellent for clothing characterized by being a component. 3. Effective use of 2,3,5,6-tetrafluoro-4-methylbenzyl (1R) -trans-3- (2-chloro-2-fluorovinyl) -2,2-dimethylcyclopropanecarboxylate An insect repellent for clothing characterized by being a component.