JP2929654B2 - Insect repellent composition - Google Patents

Description

The present invention relates to a novel insect repellent composition.

<Conventional technology> Formula [I] 1-ethynyl-2-methyl-2-pentenyl chrysantheate represented by the formula (1) is an insecticidal compound described in JP-B-55-42045, and is known to have an excellent effect of preventing damage to clothing pests. No. 56-9904.

<Problems to be Solved by the Invention> However, when the compound is used or stored for a long period of time under particularly severe conditions, for example, under strong light scattering or high temperature conditions, an off-flavor may sometimes be observed. Therefore, some measures to prevent off-flavors were required.

<Means for Solving the Problems> The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that an active ingredient compound represented by the formula [I] has the following group [I
I] The present inventors have found that the generation of off-flavor can be prevented by adding one or more compounds selected from the group, and have reached the present invention.

That is, the present invention provides an insect repellent composition containing the active ingredient compound represented by the above formula [I] and one or more compounds selected from the group [II].

Group [II] as an additive in terms of the effect of preventing off-flavor generation
Among them, 2,2'-methylenebis (4-ethyl-6-tert
-Butylphenyl), 2,4-di-tert-butylphenyl, 3,5-di-tert-butyl-4-hydroxybenzoate are more preferred.

In the present invention, the mixing ratio between the active ingredient compound represented by the formula (I) and the compound selected from the group (II) is usually 1: 1 to 100: 1 by weight, preferably 5: 1 to 100: Is one. When mixing both or holding them on a carrier, auxiliary agents such as an organic solvent, a synergist, a surfactant, a fragrance, and a bactericide / fungicide may be used as necessary.

 Examples of the organic solvent include kerosene and alcohols
And so on. As synergists, for example,
Lolodipropyl ether (S-421 ), Α- [2-
(2-butoxyethoxy) ethoxy] -4,5-methylene
Dioxy-2-propyltoluene (piperonyl butoxy)
C), N- (2-ethylhexyl) -bicyclo [2,2,
1] Hept-5-ene-2,3-dicarboximide (MGK
−264 ).

Further, benzotriazole derivatives described in JP-A-61-30505, JP-A-63-122608, and JP-A-63-122608
By adding the compound described in 126808 publication,
It is also possible to simultaneously prevent discoloration at a site stained with copper, a copper alloy, or a copper-containing dye.

These copper discoloration preventing additives include the following groups (II
I] Each compound shown in is mentioned.

From the viewpoint of the copper discoloration preventing effect and the like, among the group [III], benzotriazole and 1H-tetrazole are more preferable as the copper discoloration preventing additive.

In the present invention, the amount of the compound selected from the group [III] is usually 1/100 of the active ingredient compound represented by the formula [I].
１1 times by weight, preferably 1/100 to 1/5.

Compound [I] can be synthesized by the method described in JP-B-55-42045. Further, the compound [I] has an optically active isomer due to an asymmetric carbon on the alcohol side and the acid side, and a geometric isomer due to a cyclopropane ring on the acid side. Includes isomers and mixtures thereof.

The composition of the present invention can be used, for example, as an insect repellent for clothing. In that case, the composition of the present invention as it is, for example,
Although it can be applied to clothes storage furniture such as clothes dance, Japanese dance, rearranged dance, etc., it is usually used after adjusting to a formulation such as a plate using a suitable carrier. At that time, the content of the composition of the present invention contained in the preparation is usually 0.1 to 80% by weight.

<Examples> Hereinafter, the present invention will be described in more detail with test examples, but the present invention is not limited to these test examples only.

Test Example 1 To 4 mg of 1-ethynyl-2-methyl-2-pentenyl d-cis, trans-chrysanthemate (hereinafter referred to as empensulin), 0.4 mg of each of the compounds shown in Table 1 below was added, and the mixture was added to acetone. After dissolution, the acetone solution was
It was applied to a filter paper of × 1 cm and air-dried. The filter paper thus adjusted was placed in a 5 ml screw tube and covered with aluminum foil. After being kept in a constant temperature bath at 80 ° C. for 72 hours, the filter paper was taken out and the degree of odor generation was observed.

 The degree of odor was determined according to the following criteria.

No odor 0 Slight odor 1 Odor 2 Observation of odor was performed by three persons, and the numerical values (0 to 2) of three persons were averaged, rounded and displayed.

 The results are shown in Table 1.

Test Example 2 Each of the compounds listed in Table 1 below was added to empensulin 100 mg.
After adding 0 mg and dissolving in acetone, the acetone solution was applied to a 5 cm × 5 cm filter paper and air-dried. Put the filter paper prepared in this way into a 9 cm diameter petri dish, 900
A xenon lamp light of 0 to 10,000 lux was irradiated for 24 hours.
Next, the filter paper was taken out and the degree of odor was observed.

 The degree of odor was determined based on the same criteria as in Test Example 1.

 The results are shown in Table 1.

As is clear from Table 1, by adding a compound selected from the group [II], even under a heating condition of 80 ° C. for 72 hours or a severe light irradiation condition of irradiation of a xenon lamp of 900 to 10,000 lux, Excellent off-flavor prevention effect was observed.

Test Example 3 Empenthrin 4 mg in 2,4-di-tert-butylphenyl
0.4 mg of 3,5-di-tert-butyl-4-hydroxybenzoate or 2,2'-methylenebis (4-ethyl-6
-Tert-butylphenol) was added, and 0.4 mg of benzotriazole or 0.4 mg of 1H-tetrazole was further added and dissolved in acetone. The acetone solution was applied to a 1 cm × 1 cm filter paper and air-dried. In the same manner as in Test Examples 1 and 2, the odor after being kept under the heating condition and the light irradiation condition was observed.
In addition, the filter paper impregnated with the above agent was sandwiched between copper plates of 5 cm x 5 cm, the edges were closed with cellophane tape, and placed in a 60 ° C constant temperature bath.
After holding for a time, the degree of discoloration of the filter paper was observed. The degree of discoloration was determined based on the following criteria.

No discoloration 0 Slight discoloration 1 Discoloration 2 Observation of the degree of discoloration was performed by three persons, and the numerical values (0 to 2) of three persons were averaged, rounded and displayed.

 The results are shown in Table 2.

<Effect of the Invention> The insect repellent composition of the present invention is an excellent composition that can surely prevent the generation of off-flavors and can also reliably prevent copper discoloration by adding a compound selected from the group [III]. .

──────────────────────────────────────────────────続 き Continuation of front page (56) References JP-A-59-116202 (JP, A) JP-A-63-122608 (JP, A) JP-A-61-30505 (JP, A) JP-A 54-116 98324 (JP, A) JP-A-63-126808 (JP, A) JP-A-63-48201 (JP, A) JP-A-56-55303 (JP, A) JP-B-46-21239 (JP, B1) JP-B-47-18667 (JP, B1) (58) Fields investigated (Int. Cl. ⁶ , DB name) A01N 53/00 A01N 25/22

Claims (2)

(57) [Claims] 1. The formula [I] A method for preventing an unpleasant odor of an insect repellent containing the active ingredient, comprising adding one or more compounds selected from the following group [II] to the active ingredient compound represented by the formula (1). 2. The method according to claim 1, wherein one or more compounds selected from the following group [III] are further added in addition to the one or more compounds selected from the group [II].