JP2002187802A - Vermin repellent composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a vermin repellent composition, not only having an excellent vermin-repellent effect for a long period, but also having excellent effectiveness in the initial stage of its application. SOLUTION: This vermin repellent composition contains (1) 1S,3R,4R,6R- carane-3,4-diol and (2) a mono-substituted alkylene glycol compound which has a vapor pressure of 0.001-0.3 mmHg at 25 deg.C and is expressed by the general formula (1): R1-O-(CH(R2)CH(R3)O-)n-H (R1 is a 3-8C alkyl, phenyl or a 7-8C phenylalkyl; R2 and R3 are each H or methyl, and identical to or different from each other, provided that both R2 and R3 are not methyl; and n is 1-3).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a pest repellent composition.

[0002]

2. Description of the Related Art It has been disclosed that pest repellents containing certain monoterpenediol compounds have excellent repellency against blood-sucking pests and sanitary pests.
No. 6,086,045. The publication describes 1S, 3R, 4R, 6R-carane-3,4-diol as one of the preferable compounds among the monoterpenediol compounds.

[0003]

However, 1S,
Although the composition containing 3R, 4R, 6R-carane-3,4-diol has an excellent repellent effect as described above, a short time (15 minutes or 3 minutes) after treating the composition.
(0 min), it was found that a phenomenon in which the repellent effect temporarily decreased occurs at the time point. Such a temporary decrease in the repellent effect after the treatment may lead to a result of being bitten by a mosquito at an initial point after the repellent treatment in a practical use, and thus solving such a problem. Was desired.

[0004]

Means for Solving the Problems The present inventors have made intensive studies under such circumstances and as a result, have found that a composition containing 1S, 3R, 4R, 6R-carane-3,4-diol and a specific monosubstituted alkylene glycol compound. However, they have found that the above problems can be solved, and have reached the present invention.

That is, the present invention relates to (1) 1S, 3R, 4R, 6
R-curane-3,4-diol (hereinafter referred to as the present compound) and (2) a vapor pressure at 25 ° C of 0.001 to 0.001;
A 0.3 mmHg, and the general formula ^{(1) R 1 -O- (CH} (R 2) CH (R 3) O-) n-H (1) ( wherein the alkyl group of R ¹ is C3~C8 , A phenyl group or a C6-C8 phenylalkyl group, wherein n is 1
Represents an integer of ~ 3. Although R ² and R ³ represents a hydrogen atom or a methyl group the same or different, R ² and R ³
Are not methyl groups. The present invention provides a pest repellent composition (hereinafter, referred to as the present composition) containing a monosubstituted alkylene glycol compound represented by the following formula (hereinafter, referred to as the present glycol compound).

[0006]

BEST MODE FOR CARRYING OUT THE INVENTION The present compound which is a pest repellent active ingredient in the present composition can be produced, for example, by the method described in JP-A-5-4901. The content of the present compound in the present composition is usually 0.1 to 50% by weight, preferably 0.2 to 40% by weight.

[0007] In the present invention, the vapor pressure of the present glycol compound is determined by Stephen F. et al. J by Donovan
own of Chromatography A.
749 (1996) 123-129. It is a value obtained by a temperature-increasing gas chromatograph method measured according to the method described in 123-129. The vapor pressure of the present glycol compound at 25 ° C. is 0.001 to 0.3 mmHg,
It is preferably in the range of -0.2 mmHg.

As the glycol compound, for example, diethylene glycol mono-n-butyl ether (0.16
mmHg), 2-phenoxyethanol (0.11 mm
Hg), propylene glycol monophenyl ether (0.073 mmHg), ethylene glycol mono 2-
Ethylhexyl ether (0.064 mmHg), dipropylene glycol mono-n-butyl ether (0.0
57 mmHg), 2-benzyloxyethanol (0.
043 mmHg), triethylene glycol mono-n-
Butyl ether (0.039 mmHg), diethylene glycol mono-n-hexyl ether (0.0097 m
mHg), dipropylene glycol monophenyl ether (0.0025 mmHg), diethylene glycol monophenyl ether, diethylene glycol mono 2-ethylhexyl ether (0.002 mmHg), and the like, alone or in a mixture of two or more. (The numerical value in parentheses after the present glycol compound example indicates the vapor pressure of the compound at 25 ° C.). Among them, diethylene glycol mono n
-Butyl ether, diethylene glycol mono n-hexyl ether, triethylene glycol mono n-butyl ether and diethylene glycol mono 2-ethylhexyl ether are preferred. The content of the present glycol compound in the present composition is usually 0.2 to 90% by weight, preferably 0.2 to 60% by weight, more preferably 0.3 to 5% by weight.
0% by weight.

The present composition usually contains a solvent in addition to the present compound and the present glycol compound. Examples of such a solvent include alcohols such as ethanol, various types of denatured ethanol, isopropyl alcohol, phenethyl alcohol, and cinnamon alcohol; polyalkylene glycols such as diethylene glycol, triethylene glycol, dipropylene glycol, and tripropylene glycol; IP-162.
Hydrocarbons such as isoparaffins such as 0, IP-2028, and IP-2835 (these are the product names of Idemitsu Petrochemical Co., Ltd.) and normal paraffins such as Norpar 15 (a product name of Exxon Chemical Co., Ltd.);
Animal and vegetable oils such as terpineol, olive oil, soybean oil, rapeseed oil, castor oil, corn oil, linseed oil, coconut oil, palm oil, jojoba oil, safflower oil; isopropyl myristate, ethylene glycol monocaprylate, ethylene glycol monocaproate , Monoesters such as propylene glycol monocaprylate, esters such as dibasic acid diesters such as diisopropyl adipate and diisobutyl adipate; ketones such as aniseal acetone; ethers such as tetrahydrofuran, dioxane and perfluoropolyether Classes: methylpolysiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, methylphenylpolysiloxane, poly (oxyalkylene) methylpolysiloxane copolymer, methyl hydrogen Silicone compounds such as polysiloxane and the like. When the present composition contains the solvent, the content is usually 5 to 99% by weight.

The present composition may contain various isomers of the present compound, and if necessary, piperonyl butoxide (PBO), N- (2-ethylhexyl) -bicyclo [2,2,1]. Synergists such as hepta-5-ene-2,3-dicarboximide (MGK264) and octachlorodipropyl ether (S421), phenols such as dibutylhydroxytoluene (BHT), tocophenol (vitamin E) and the like Antioxidants, ultraviolet absorbers such as sinoxate and oxybenzone, humectants such as glycerin, urea and lactate, natural or synthetic flavors such as anise oil, basil oil and citronella oil, coloring such as red No. 2 and blue No. Ingredients, diet, P-menthane-3,8-diol, hyssop oil, KBR-3023 (1-piperidinecarboxylic acid, 2- 2-hydroxyethyl) -, 1-
Other pest repellent components such as methyl propyl ester) may be contained.

In addition, for the purpose of facilitating uniform spreading on the skin when the present composition is applied and facilitating formation of a coating film comprising the present composition, for example, triethanolamine caprylate, triethanol caprate An amine salt of an organic acid such as an amine, triethanolamine pyrrolidonecarboxylate, and N-coconut fatty acid acyl-L-glutamate triethanolamine may be contained in the present composition.

The present composition comprises the present composition, the present glycol compound, and, if necessary, a solvent and other components, usually at room temperature to
It can be manufactured by mixing and stirring until the mixture becomes uniform at about 50 ° C.

The present composition can be used as a pest repellent by applying and spraying it to human skin such as arms, feet and face as well as clothing covering the skin. Further, the composition and the propellant are sealed in a pressure-resistant container to form an aerosol, and the aerosol can be used as a pest repellent by spray-coating in the same manner.

Examples of pests that can be repelled by the present composition include various pests and arthropods such as mites. The present composition is particularly suitable for Culex pipiens such as Culex pipiens, Aedes albopictus, Aedes albopictus such as Aedes albopictus, Anopheles such as Aedes albopictus, Anopheles spp.
Flying pests represented by dipteran pests such as house fly, housefly, housefly, slime fly, blowfly, blowfly, blowfly, fly fly, flies, blackflies, sand flies, flies, and flies Suitable for repellent applications.

[0015]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. Example 1 0.5 g of the present compound and 2-phenoxyethanol (manufactured by Kanto Chemical Co., Ltd., reagent) in a 10-mL volumetric flask.
5 g were weighed. 99% ethanol (manufactured by Kanto Kagaku Co., Ltd., reagent) was added and uniformly dissolved, and the total amount was made 10 mL with 99% ethanol, and the composition 1 (specific gravity (20 ° C.)
= 0.822).

Example 2 This composition 2 was prepared in the same manner as in Example 1 except that diethylene glycol monobutyl ether (reagent, manufactured by Wako Pure Chemical Industries, Ltd.) was used instead of 2-phenoxyethanol.
(Specific gravity (20 ° C.) = 0.814) was obtained.

Example 3 The amount of diethylene glycol monobutyl ether was adjusted to 1.0
This composition 3 (specific gravity (20 ° C.) = 0.829) was obtained in the same manner as in Example 2 except that the amount was changed to g.

Example 4 The same procedure as in Example 1 was carried out except that diethylene glycol mono-n-hexyl ether (reagent, manufactured by Wako Pure Chemical Industries, Ltd.) was used instead of 2-phenoxyethanol, and the composition 4 (specific gravity (20 ° C) = 0.810).

Example 5 A composition 5 (specific gravity (20 ° C.) = 0.938) was obtained in the same manner as in Example 4 except that the amount of diethylene glycol mono-n-hexyl ether was changed to 1.0 g.

Example 6 This composition 6 (specific gravity (20 ° C.) = 0) was prepared in the same manner as in Example 1 except that diethylene glycol-2-ethylhexyl ether (Nippon Emulsifier Co., Ltd., EHDG) was used instead of 2-phenoxyethanol. .810).

Example 7 This composition 7 (specific gravity (20 ° C.) = 0.816) was obtained in the same manner as in Example 6, except that the amount of diethylene glycol-2-ethylhexyl ether was changed to 1.0 g.

Comparative Example 1 0.5 g of 1S, 3R, 4R, 6R-calane-3,4-diol was weighed into a 10-mL volumetric flask. 99% ethanol (manufactured by Kanto Chemical Co., Ltd., reagent) was added and uniformly dissolved, and the total amount was further made 10% with 99% ethanol to obtain Comparative Composition 1 (specific gravity (20 ° C.) = 0.806).

Comparative Example 2 A comparative composition 2 (specific gravity (20 ° C.) = 0.814) was obtained in the same manner as in Comparative Example 1 except that the amount of the present compound was changed to 1.0 g.

Comparative Example 3 In a 10-mL volumetric flask, 0.5 g of 2-phenoxyethanol (manufactured by Kanto Chemical Co., Ltd.) was weighed. 99%
Ethanol (manufactured by Kanto Chemical Co., Ltd., reagent) was added and uniformly dissolved, and the total amount was further made 10% with 99% ethanol to obtain Comparative Composition 3 (specific gravity (20 ° C.) = 0.800).

Comparative Example 4 Comparative composition 4 (specific gravity (20 ° C.) = 0) was performed in the same manner as in Comparative Example 3 except that diethylene glycol monobutyl ether (a reagent manufactured by Wako Pure Chemical Industries, Ltd.) was used instead of 2-phenoxyethanol. .807).

Comparative Example 5 (00629-153) Comparative composition 5 was prepared in the same manner as in Comparative Example 3 except that diethylene glycol mono n-hexyl ether (reagent, manufactured by Wako Pure Chemical Industries, Ltd.) was used instead of 2-phenoxyethanol. (Specific gravity (20 ° C.) = 0.798) was obtained.

Comparative Example 6 Comparative composition 6 (specific gravity (20 ° C.) was prepared in the same manner as in Comparative Example 3 except that diethylene glycol mono 2-ethylhexyl ether (reagent, manufactured by Wako Pure Chemical Industries, Ltd.) was used instead of 2-phenoxyethanol. ) = 0.808).

Comparative Example 7 (00630-156) A comparative composition 7 (specific gravity (20 ° C.) = 0.802) was prepared in the same manner as in Comparative Example 6 except that the amount of diethylene glycol mono-2-ethylhexyl ether was changed to 1.0 g. Obtained.

Example 8 This composition 8 (specific gravity (20 ° C.) = 0.821) was prepared in the same manner as in Example 1 except that diethylene glycol monophenyl ether (manufactured by Yokkaichi Gosei Co., Ltd.) was used instead of 2-phenoxyethanol. I got

Example 9 This composition 9 (specific gravity (20 ° C.) = 0.821) was prepared in the same manner as in Example 1 except that propylene glycol monophenyl ether (manufactured by Yokkaichi Gosei Co., Ltd.) was used instead of 2-phenoxyethanol. ) Got.

Example 10 In a 10-mL volumetric flask, 0.5 g of the present compound and 0.3 g of 2-phenoxyethanol (reagent, manufactured by Kanto Chemical Co., Ltd.)
And 0.3 g of IP-2028 (hydrocarbons, trade name, manufactured by Idemitsu Petrochemical Co., Ltd.). Add 99% ethanol (Kanto Chemical Co., Ltd., reagent) and dissolve uniformly,
Further, the total amount was adjusted to 10 mL with 99% ethanol to obtain the present composition 10 (specific gravity (20 ° C.) = 0.814).

Example 11 In a 10 mL volumetric flask, 0.5 g of the present compound, 0.9 g of diethylene glycol monobutyl ether and 0.1 g of methylphenylpolysiloxane (trade name: silicone KF-54, manufactured by Shin-Etsu Chemical Co., Ltd.) were weighed. . 9
9% ethanol (manufactured by Kanto Chemical Co., Ltd., reagent) is added and uniformly dissolved, and the total amount is further 10 mL with 99% ethanol.
The composition 11 (specific gravity (20 ° C.) = 0.826)
I got

Example 12 The same procedure as in Example 3 was repeated, except that triethylene glycol monobutyl ether was used instead of diethylene glycol monobutyl ether, to obtain the composition 12 (specific gravity (20 ° C.)
= 0.827).

Test Example 1 Cage (48 cm) covered with 80 mesh nylon net
Aedes ag (Aedes ag)
ipti) About 500 adults were released. A portion of the polyethylene disposable elbow cover is cut out so that a rectangular (5 cm × 10 cm) opening is formed in the upper arm when the person wears the elbow cover on the arm. A double-sided tape having a width of about 1 cm is adhered to the inside of the elbow cover along the opening formed by cutting out the rectangle. The disposable elbow cover with double-sided tape is applied to the upper arm, and the disposable elbow cover is attached to the upper arm with double-sided tape so that only the rectangular portion is exposed. A styrofoam tape (thickness: 3 mm, width: 1 cm) is attached to a boundary around the rectangular opening. Composition 1 shown in Tables 1 and 2 in the rectangular opening of the upper arm
Fifty microliters are evenly applied, and after 15 minutes from the application, the upper arm is inserted into the cage, attracted to the rectangular opening exposed for 120 seconds, and the number of insects remaining (mosquito fusion) is counted. Also, after 120 seconds, pull out the upper arm from the cage,
Count the number of stings (mosquito bites). The test is stopped if there are two or more stings. The same test as described above was performed 30 minutes and 1 hour after application of the composition. The results are shown in Tables 1 and 2.

[0035]

[Table 1] 1: 2-phenoxyethanol 2: diethylene glycol mono n-butyl ether 3: diethylene glycol mono n-hexyl ether * 4: diethylene glycol mono 2-ethyl exyl ether

[0036]

[Table 2]

[0037]

According to the present invention, not only the pest repellent effect for a long period of time, but also the phenomenon that the efficacy is temporarily reduced in the early stage of application, which has conventionally been a problem in the composition containing the present compound, can be prevented. Pest control agents can be provided.

Claims (5)

[Claims] (1) 1S, 3R, 4R, 6R-Kalan-
3,4-diol and (2) a vapor pressure at 25 ° C. of 0.001 to 0.3 mmHg and a general formula (1) R ¹ —O— (CH (R ² ) CH (R ³ ) O—) n—H (1) (wherein, R ¹ represents a C3-C8 alkyl group, a phenyl group or a C7-C8 phenylalkyl group, and n is 1
Represents an integer of ~ 3. Although R ² and R ³ represents a hydrogen atom or a methyl group the same or different, R ² and R ³
Are not methyl groups. A pest repellent composition comprising the monosubstituted alkylene glycol compound represented by the formula (1). 2. 1S, 3R, 4R, 6R-calane-3,4
The pest repellent composition according to claim 1, wherein the content of the diol is 0.1 to 40% by weight. 3. The pest repellent composition according to claim 1, wherein the content of the mono-substituted alkylene glycol compound (1) is 0.2 to 60% by weight. 4. The monosubstituted alkylene glycol compound (1) has a vapor pressure at 25 ° C. of from 0.002 to 0.2 m.
The pest repellent composition according to any one of claims 1 to 3, which is mHg. 5. The monosubstituted alkylene glycol compound is at least one selected from diethylene glycol mono n-butyl ether, diethylene glycol mono n-hexyl ether, triethylene glycol mono n-butyl ether and diethylene glycol mono 2-ethylhexyl ether. 4. The pest repellent composition according to any one of 4.