JPH01168602A - Repellent against sanitary insect pest - Google Patents

Abstract

PURPOSE:To obtain the title preparation showing excellent repelling effects on cockroaches, mosquitoes, etc., with a relatively small amount used, comprising a cyclic amine derivative such as N-methylpiperazine, piperidine, pyrrolidine or morphorine or a salt thereof as an active ingredient. CONSTITUTION:A repellent against sanitary insect pests comprising a compound (e. g., 1-octyl-4-methyl-piperazine) shown by formula I (A is group selected from groups shown by formula II-formula V; n is 8-12) or a salt thereof as an active ingredient. The repellent is capable of showing more excellent repelling effects than an existing one.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a sanitary pest repellent based on a cyclic amine derivative.

(Prior Art) Dimethyl terephthalate, diethyl toluamide (hereinafter abbreviated as DEET), and the like are widely known as repellents for sanitary pests such as cockroaches and mosquitoes. Also,
rMosq, NeWSJ 1975.35 (2), p.
204-210 (UK), n-acylamide and n-
The repellent effects of alkylsulfonamides and the like have been reported.

[Problem that the invention seeks to solve]

However, conventional repellents made of DEET and the like have a drawback in their repellent effect.

An object of the present invention is to provide a sanitary pest repellent that has particularly excellent repellent effects and can be used as an alternative to the conventional repellents mentioned above.

[Technical means to solve problems]

The sanitary pest repellent according to the present invention has the following formula: ,n
is an integer from 8 to 12. ) The active ingredient is a cyclic amine derivative or a salt thereof.

The cyclic amine derivatives of general formula (I) can be prepared by known methods, for example by directly alkylating a cyclic amine such as N-methylbiperazine, piperidine, pyrrolidine or morpholine, or by first converting the acyl with an acid halide. and reducing the obtained acyl derivative with lithium aluminum hydride, aluminum hydride, lithium aluminum hydride/aluminum chloride, etc.

Specific examples of the above-mentioned cyclic amine derivatives include 1-octyl-4-methyl-piperazine (MPL8), 1-octyl-4-methyl-piperazine (MPL8), methylbiperazine derivative (hereinafter, when abbreviated, the number of carbon atoms in the alkyl group is added to MPL). It includes decyl-4-methyl-piperazine (MPLIO), 1-dodecyl-4-methyl-piperazine (MPL12), etc., and is called a piperidine derivative (hereinafter, when abbreviated, the number of carbon atoms in the alkyl group is added to PPL). , N-octyl-piperidine (PPL8), N-decyl-piperidine (PPLIO)
, N-dodecyl-piperidine (PP L 12 ,), etc., and as pyrrolidine derivatives (hereinafter, when abbreviated, the number of carbon atoms in the alkyl group is added to PRL),
N-decyl-pyrrolidine (PPL8), N-decyl-
Pyrrolidine (PRLIO), N-dodecyl-pyrrolidine (PPL12), etc. are included, and morpholine derivatives (
Hereinafter, when abbreviating, the number of carbon atoms in the alkyl group is added to MOL), N-cutyl-morpholine (MOL
8), N-decyl-morpholine (MOLIO), N-dodecyl-morpholine (MOL12), and the like.

The salt of the cyclic amine derivative can be easily obtained, for example, by dissolving the above-mentioned cyclic amine derivative in ether and passing hydrogen chloride gas through the solution.

[For production]

The cyclic amine derivatives represented by the general formula CI) and their salts have excellent repellency against cockroaches, mosquitoes, etc., and therefore can be suitably used as active ingredients in sanitary pest repellents.

Below, those cyclic amine derivatives (MPL, PPL,
Using PRL, MOL8-12) as test specimens, the repellent efficacy against cockroaches (German cockroach, Black cockroach) and mosquitoes Culex pipiens, Aedes albopictus) and the effective amount thereof will be explained based on each repellent efficacy test. Note that commercially available DEET is used as a comparison sample.

<a> Repellent efficacy against German cockroach (a-1) Test method 41 cm (W) x 32 cm (D) x 22 cm (H
), 50 adult German cockroaches (male:male = 1:1) were released in a plastic case, and placed in a dark room at 27°C for 2 to
The German cockroach was allowed to stand still for 3 hours to stabilize it.

Thereafter, a sample-treated No. 120 paper (processing amount: 0.025 to 2 g/m2) and an untreated No. 20 paper with a diameter of 11 cm were placed in the case, and a sheet of known weight was placed in the center of each opening paper. I placed a sugar cube.

After standing in a dark room at 27°C for three days, the amount of sugar cubes eaten on each paper was measured, and the repellency rate was calculated using the following formula. Note that the test was conducted in duplicate.

(a-2) Test results The test results are shown in Table 1 below.

Table-1 Repellency rate (%) against German cockroaches - As is clear from the above test results, the repellent effects of MPL, PPL, PRL and MOL8-12 against German cockroaches are superior to DEET when compared with the same treatment amount, and among them MPL8, ppLIO1PRL8 and PRLIO exhibit an excellent repellent effect even at a treatment amount of 0.1 g/m2, and other substances generally exhibit an excellent repellent effect at a treatment amount of 0.5 g/m2 or more.

<b> Repellent efficacy against black cockroach (b-2) Test method 61 cm (W) x 40 cm (D) x 22 cm ()
There are adult black cockroaches 3 in the plastic case of I).
The test was conducted in the same manner as for German cockroaches, except that 0 cockroaches (male:male=1:1) were released and the sugar cube feeding period was one day, and the repellency rate (%) was calculated.

(b-2) Test results The test results are shown in Table 2 below.

Table-2 Repellency rate (%) against black cockroaches As is clear from the above test results, MPL8 against black cockroaches
-12, PPL9-12, and PPL12 are far superior to DEET when compared at the same processing amount, and the repellent effects of MPL8 and PPL12 are particularly remarkable.

<C> Feeding repellent efficacy against German cockroach (c −
1) Test method Place sugar cubes treated with an appropriate amount of the test sample (treatment amount 0.002-2 mg/piece) on untreated N0020 paper.
A test was conducted according to the test method in a-1), and the feeding repellency rate was calculated.

(c-2) Test results The results of this test are shown in Table 3 below. Note that the addition of rHcJ in the table means that the sample is a hydrochloride.

As is clear from the above test results, the feeding repellent effects of PPL8 and MOL12 against German cockroaches are considerably superior to DEET when compared at the same treatment amount.

It should be noted that these hydrochloride salts are not volatile and therefore have a weak direct repellent effect as described above, but it is found that they exhibit a strong ingestion repellent effect similar to that in the free state.

<d) Repellent efficacy against mosquitoes (d-1) Test method Test insects (
Mosquitoes) were released and left for one hour to allow them to fully acclimate to the test environment. Add 100 mg of propylene glycol, 40 mg of isopropyl myristate (retention agent), and 300 mg of purified water to the test sample (amount used: 10 to 200 mg), and add 98 mg of purified water.
% ethanol to make a total amount of 2 g, mix and dissolve uniformly,
This was soaked in absorbent cotton, applied evenly over the entire mouse anesthetized with ether, and secured with a wire mesh to prevent movement.

After 1 hour, mice treated with the test sample and untreated mice were each placed in the center of the cage, and 2 hours later, all the mosquitoes were collected, the number of blood-sucking mosquitoes was counted, and the repellency rate was calculated using the following formula.

Note that absorbent cotton soaked in water was placed inside the cage for humidification. Also, the room temperature during the experiment was 28℃, and the humidity was 68%.
Met.

(d-2) Test results The test results are shown in Table 4 below.

Table 4 Mosquito repellency rate (%) As is clear from the above test results, MPL8 to 12 have excellent repellent effects, and MPL8 in particular has a
Even at 20 mg, it exhibits an excellent repellent effect equivalent to that of DEET.

(Examples) The present invention will be specifically explained below based on Examples.
The invention is not limited to these examples. Note that all "%" described in the examples are based on weight.

<Example 1> A cockroach repellent lacquer containing 1-octyl-4-methylpiperazine (MPL8) as an active ingredient is prepared according to the following formulation.

1-octyl-4-methylpiperazine 5% nitrocellulose 15% ethyl acetate
20% butyl acetate
25% toluene 25
% Butanol 5% Acetyl Triethyl Citrate 5% This lacquer-like repellent is applied to areas where cockroaches are thought to be infested. After drying, the lacquer forms a transparent film, in which the active ingredient MPL8 is fixed to the applied area and exerts the desired repellent effect.

<Example 2> A solid waxy cockroach repellent containing N-decyl-piperidine (PPLIO) as an active ingredient is prepared according to the following formulation.

N-decyl-piperidine 10% carnauba wax 4% liquid lanolin
81% castor oil
5% First, each component is heated and dissolved at 80° C., mixed and stirred to be uniform, and then 50 g is poured into a metal and allowed to cool to form a solid.

This solid wax-like cockroach repellent is placed in a container with a suitable opening and placed in a place where cockroaches are thought to be infested.

The active ingredient PPLIO in the solid material exerts the desired repellent effect.

<Example 3> A cockroach repellent in the form of a solid molded article containing N-dodecyl-pyrrolidine (PRL12) as an active ingredient is prepared according to the following formulation.

N-dodecyl-pyrrolidine 10% talc
70% precipitated calcium carbonate 10% liquid paraffin
2% octyl palmitate
8% First, N-dodecyl-pyrrolidine, talc, and precipitated calcium carbonate are placed in a ribbon mixer and mixed well, and then a mixture of liquid paraffin and octyl palmitate, which has been uniformly dissolved in advance, is added and mixed well. Next, 50 g of powder obtained by pulverizing the obtained mixture is placed in a metal and compression molded to obtain a solid molded product.

This solid cockroach repellent is also used in the same manner as in Example 2. The active ingredient PRL12 in the solid molded product exhibits the desired repellent effect.

<Example 4> A liquid repellent for Culex pipiens, Aedes albopictus, etc. that is harmless to the body and contains 1-octyl-4-methyl-piperazine (MPL8) as an active ingredient is manufactured by A according to the following formulation.

1-octyl-4-methyl-piperazine 10% 1,3-butylene glycol 5% water
15%9
8% ethanol 70% first MPL
Dissolve 8 in ethanol, and when it is completely dissolved, 1.3
- Add butylene glycol and water and mix and stir to form a homogeneous liquid.

This liquid repellent is applied to exposed areas of the body.

The active ingredient MPL8 in the liquid exhibits the desired repellent effect and prevents blood sucking by Culex pipiens, Aedes albopictus, etc.

(Effects of the Invention) As described above, the present invention provides a sanitary pest repellent of a cyclic amine derivative that exhibits an excellent repellent effect against cockroaches, mosquitoes, etc. with a relatively small amount of treatment and use. be able to.

that's all Agent Patent Attorney Atsushi Yasufuji

Claims (1)

[Claims] (1) General formula A-(CH_2)_n_-_1CH_3 (In the formula, A is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. A group selected from the group consisting of ▼ and ▲ with mathematical formulas, chemical formulas, tables, etc., where n is an integer from 8 to 12) Hygiene containing a cyclic amine derivative or its salt as an active ingredient Pest repellent.