JPH0812506A - Clothing pest inspect repellent having antimicrobial effect - Google Patents

Abstract

PURPOSE:To provide a clothing pest insect repellent containing a specific quaternary ammonium salt as an active component and optionally further a pyrethroid compound, harmless to human body, free from disagreeable smell, available at a low cost, soluble in a dry cleaning solvent and exhibiting antimicrobial effect. CONSTITUTION:This clothing pest insect repellent having antimicrobial effect is produced by using an antimicrobial quaternary ammonium salt of formula I [R<1> is an alkyl or an alkenyl; R<2> and R<3> are each an alkyl; R<4> is an alkylene; (m) is 1 or 2; (n) is 1-5; X is an alkylphosphoric acid ester ion or a polyoxyalkylene alkyl ether phosphate ion expressed by formula II or formula III (R<5> and R<6> are each an alkyl, etc.)] as an active component. The active componenl is preferably used in combination with a pyrethroid compound. The quaternary ammonium salt of formula I improves the residual activity and the biting damage preventing property of pyrethroid compound. The compound of formula I has high repelling effect on clothing pest insects represented by the larvae of black carpet beetle and varied carpet beetle and excellent biting damage preventing property.

Description

Detailed Description of the Invention

[0001]

The present invention relates to a pest repellent for clothing. More specifically, the present invention relates to a pest repellent for clothing, which is mainly used as a chemical for dry cleaning and contains a quaternary ammonium salt having a novel antibacterial property as an active ingredient.

[0002]

2. Description of the Related Art Larvae such as scabbard beetles, beetles, scabbards, and squids have been regarded as representatives of clothing pests because they damage wool, silk-made clothes, and fur. Conventionally,
In order to repel such clothing pests or suppress feeding damage, sublimable insect repellents such as paradichlorobenzene, naphthalene and camphor, and contact insect repellents of pyrethroid compounds such as permethrin and etofenprox are used.

[0003]

However, the above-mentioned sublimable insect repellents are not only limited in their use because they have a weak effect of preventing food damage, no persistence, and a strong odor. Since it is insoluble, it cannot be used for dry cleaning. On the other hand, the contact insect repellent has a strong food damage prevention effect, but is expensive, and has a drawback that the residual effect is superior to the sublimable insect repellent but still weak.
Regarding the antibacterial effect, no effect is seen. Also,
Recently, various odorous and odorless synthetic insect repellents have been developed, but they are harmless to the human body, produce no offensive odor, and are not soluble in dry cleaning solvents. It has the drawback of being very expensive.

In view of these circumstances, the present invention is a pest repellent for clothing, which is harmless to the human body, does not produce an offensive odor, is inexpensive, is soluble in a solvent for dry cleaning, and has an antibacterial effect. It is intended to provide.

[0005]

Means for Solving the Problems As a result of intensive studies to achieve the above object, the present inventors have found that a quaternary ammonium salt having antibacterial properties eliminates the above-mentioned drawbacks, and
It was found that the pyrethroid compound also improves the residual efficacy and the food damage prevention property, and the present invention has been completed based on these findings.

That is, according to the present invention, the following general formula (1)

[0007]

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[In the above formula, R ¹ represents an alkyl or alkenyl group having 8 to 14 carbon atoms, R ² and R ³ represent an alkyl group having 1 to 2 carbon atoms, and R ⁴ represents 2 to ⁴ carbon atoms. Represents an alkylene group of, m is an integer of 1 or 2, n is an integer of 1 to 5, X is the following general formula (2) or (3).

[0009]

[Chemical 4]

(In the above formula, R ⁵ and R ⁶ have 2 to 1 carbon atoms.
4 represents the residue of a polyoxyalkylene ether obtained by adding an alkylene oxide to an alkyl group of 4 or an aliphatic alcohol having 2 to 14 carbon atoms) or a polyoxyalkylene alkyl ether phosphate ester Represents an ion. However,
When m is 2, X is represented by the above general formulas (2) and (3).
May be a single ion or a mixture thereof], and a pest repellent for clothing, comprising a quaternary ammonium salt having an antibacterial property represented by .

The above-mentioned quaternary ammonium salt compound has a high repellent effect against clothing pests represented by larvae such as Pleurotus cerevisiae and Pseudococcidae, and is excellent in food damage prevention. The compound represented by the general formula (1) can be synthesized, for example, as follows.

A neutralizing equivalent of an alkyl phosphate ester or a polyoxyalkylene alkyl ether phosphate ester is added to 1 mol of the trialkylamine to neutralize the solution to obtain an aqueous solution. This solution is heated at 50 to 110 ° C (preferably 10 ° C).
The temperature is raised to 0 ° C.), and 1 to 5 mol (preferably 1 to 2 mol) of ethylene oxide, propylene oxide or butylene oxide is introduced into this to obtain the desired product. The compound synthesized in this manner is excellent in repellent effect against food pests and food damage prevention property, and also has antibacterial effect,
Furthermore, when used in combination with a pyrethroid compound, it has the effect of synergistically improving the residual efficacy and the food damage prevention property.

[0013]

EXAMPLES Next, the present invention will be further described with reference to examples, but the present invention is not limited to these examples. Representative examples of compounds of general formula (1) useful in the present invention are shown in Table 1 below. Where the symbols R ¹ , R ² , R ³ ,
R ⁴ , R ⁵ , R ⁶ and n are represented by the general formulas (1), (2)
And the same as the symbols in (3).

[0014]

[Table 1]

All of these compounds are solvents for dry cleaning (tetrachloroethylene, 1,1,1-
It was soluble in trichloroethane and petroleum solvent. Example 1 In order to confirm the insecticidal and antibacterial properties of the pest repellent for clothing of the present invention, the above compound 2 and some control compounds were tested under the following conditions. (1) Insect repellent test Specimens: larvae of the beetle larvae, larvae of the beetle larvae Operation: Glass petri dish (diameter 4 cm, height 2 cm), insect-treated wool cloth (2.5 x 2.5 cm) and 20 worms , And check the amount of food damage under the conditions of 28 ° C., 65% RH, and 2 weeks.

Test worm weight: 51 mg / 20 larvae of the larvae of Scutellaria baicalensis larvae 95 mg / 20 larvae of Scutellaria japonicus Evaluation method: amount of feeding damage = 2 weeks, amount of feeding damage per 20 mice (mg) Feeding damage control index = [(feeding damage in untreated area) Amount-treatment area food damage amount) /
Untreated plot food damage amount] × 100 (it is judged to be effective when the food damage suppression index is 80 or more) (2) Antibacterial test (halo test) The test sample is placed on an agar medium inoculated with Staphylococcus aureus, and 37 ° C. After culturing the bacteria for 24 hours, the size (mm) of the Staphylococcus aureus growth inhibitory zone around the sample is measured to determine the antibacterial effect (if the inhibitory zone is present, there is an antibacterial effect. to decide). The results are shown in Table 2 below.

[0017]

[Table 2]

Example 2 In the same manner as in Example 1, the compounds shown in Table 1 were subjected to an insect repellent test and an antibacterial test. The results are shown in Table 3 below.

[0019]

[Table 3]

It can be seen that when the compound of the general formula (1) according to the present invention is used, an effect of suppressing feeding damage and an antibacterial effect can be obtained at a usage amount of 0.5 to 1% owf. Example 3 In the same manner as in Example 1, a test was conducted on the improvement of the feeding damage inhibition index by the combined use of the compound 7 in Table 1 and etofenprox. The results are shown in Table 4 below.

[0021]

[Table 4]

It can be confirmed that the use of the compound of the general formula (1) according to the present invention in combination improves the feeding damage suppressing effect of etofenprox.

Claims (2)

[Claims] 1. The following general formula (1): [In the above formula, R ¹ represents an alkyl group or an alkenyl group having 8 to 14 carbon atoms, R ² and R ³ represent an alkyl group having 1 to 2 carbon atoms, and R ⁴ is an alkylene group having 2 to ⁴ carbon atoms. Represents, m is an integer of 1 or 2, n is an integer of 1 to 5, X is the following general formula (2) or (3) (In the above formula, R ⁵ and R ⁶ represent a residue of a polyoxyalkylene ether obtained by adding an alkylene oxide to an alkyl group having 2 to 14 carbon atoms or an aliphatic alcohol having 2 to 14 carbon atoms). Represents an alkyl phosphate ester ion or a polyoxyalkylene alkyl ether phosphate ion. However, when m is 2, X may be each of the ions represented by the general formulas (2) and (3), or may be a mixture thereof]. A pest repellent for clothing, which comprises, as an active ingredient, a quaternary ammonium salt having 2. The pest repellent for clothing according to claim 1, which further comprises a pyrethroid compound.