JPH0372404A - Moth-proofing and mildew-proofing agent - Google Patents

Abstract

PURPOSE:To obtain a moth-proofing and mildew-proofing agent exhibiting excellent insecticidal, moth-proofing and mildew-proofing effect against various kinds of vermin and molds and having excellent safety by using an alkyl cinnamate as an active component. CONSTITUTION:An alkyl cinnamate of formula (R is 1-4C alkyl) (e.g. methyl cinnamate known as a perfume retainer) is used as an active component of the objective moth-proofing and mildew-proofing agent exhibiting excellent insecticidal, moth-proofing and mildew-proofing effect against various kinds of vermin and mites such as mite, cockroach, termite, fly, mosquito and wool vermin. The above active component may be used as it is, however, it is preferably diluted with a proper organic solvent such as denaturated alcohol or ether or adsorbed, mixed or dispersed to a proper carrier such as activated carbon or paper. The content of the active component in a liquid or powder preparation is about 1-10wt.%, preferably 1-5wt.% for practical purpose.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to an insect repellent and fungicide containing an alkyl cinnamate as an active ingredient. More specifically, the present invention relates to an insect repellent and antifungal agent that has excellent insecticidal and insect repellent effects against various pests such as mites, cockroaches, and termites, and has excellent antifungal properties against various molds.

[Prior Art] Cockroaches are unclean pests as food pests and disease propagators, and there is an extremely strong demand for effective control methods or agents for controlling them.

As a method or agent for controlling cockroaches, for example, menthol (Japanese Unexamined Patent Application Publication No. 55-197), which uses cockroach repellent action,
-104202), N-geranyl dimethylamine, N-citroline dimethylamine (Japanese Patent Application Laid-Open No. 58-1
No. 13105>, cinnamyl alcohol, eugenol, safrole (Japanese Patent Application Laid-open No. 105821/1982)
etc. are known.

Indoor dust mites and the like are also pests that cause damage to humans, such as allergies and insect bites. Organophosphorus insecticides, carbamate insecticides, pyrethroid insecticides, and the like are used to control these mites, but pyrethroid insecticides are relatively widely used from the viewpoint of safety.

In addition, a pest repellent containing an alkylphenol as an active ingredient that has a repellent effect against cockroaches, black ants, mites, etc. (Japanese Patent Application Laid-Open No. 78105/1982), and a combination of paraffin hydrocarbon and benzyl benzoate are also used. Acaricide (
JP-A-61-91103), insecticides for fleas, house flies, mosquitoes, ticks, etc. containing linalool (JP-A-61-8)
3103) and a tick repellent containing isobornylthiocyanoacetate (Japanese Unexamined Patent Publication No. 60-4101).

Termites are also pests that cause damage to buildings, books, clothing, underground cables, etc. For example, chlordane (1, 2, 4, 5, 6
, 7,8,8-octachlor-2,2,3a, 4.7.
7a-hexahydro-4,7-methyl-IH-indene) and the like have been used, but it is said that there are problems in terms of safety. Furthermore, termite control agents containing guaiacol or hydroxybenzene derivatives (JP-A-64-22807) and termite control agents containing sesquiterpenes are known.

Regarding mold, mold can be found not only in rooms with air conditioning and heating, in relatively humid places such as bathrooms or kitchens, but also in closets, top bags, and various foods and beverages in the refrigerator, so it is necessary to take preventative measures. has become a big problem.

Compounds that are conventional fragrance substances and have antifungal properties include:
For example, linalool, l-menthol, octylaldehyde, benzyl alcohol, anis alcohol, vanillin and biveronal (PeniciJlium
SD), etc. are known (Journal of Japan Food Industry Association, Vol. 29, p. 111, 1982).

In addition, fragrance substances such as benzaldehyde, citral, borneol, citronellol, ethyl vanillin, eugenol, geraniol, and d,l-menthol have antifungal properties (
Aspergi 11us Orizae) (Journal of Japan Food Industry Association, No. 29)
Vol. 111, 1982).

[Problems to be Solved by the Invention] However, the conventionally proposed insecticides, insect repellents, and fungicides described above are not necessarily satisfactory.

The present inventors have conducted research to develop insecticides, insect repellents, and fungicides that are effective against cockroaches, mites, flies such as termites, insect pests such as sharks, and woolly pests; and various fungi. As a result, we succeeded in developing a drug that exhibits excellent insecticidal, insect repellent, and fungicidal properties, resulting in the present invention.

That is, the object of the present invention is to have excellent insecticidal, insect repellent and fungicidal effects against various pests and fungi,
To provide an insect repellent and a fungicide that are also excellent in safety.

[Means for Solving the Problems] The present invention provides an insect repellent and fungicidal agent containing an alkyl cinnamate of the formula (wherein R represents an alkyl group having 1 to 4 carbon atoms) as an active ingredient.

The alkyl cinnamate of the present invention, such as methyl cinnamate, is a chemical substance conventionally known as a fragrance retention agent, and OeLmum
canum 51m5 (Lamiaceae), Mebouki O,
It is a substance contained in essential oils such as Basilicus L. It can also be obtained by boiling a methanol solution of cinnamic acid saturated with hydrogen chloride, or by reacting a potassium salt of cinnamic acid with WRMR methyl when cold. Other alkyl cinnamates, such as ethyl cinnamate, propyl cinnamate, and butyl cinnamate, are also known substances and can be synthesized by known methods in the same manner as methyl cinnamate.

It can also be easily obtained on the market if desired.

Although the alkyl cinnamate can be used as it is, it is preferably used after being diluted with a suitable organic solvent such as denatured alcohol or ether, or after being adsorbed, mixed or dispersed on a suitable carrier.

Examples of the carrier include diatomaceous earth, alumina, acid clay, wood flour, kaolin, bentonite, activated carbon, paper, and silica. These carriers may be used alone or as a mixture of two or more, or may be used by impregnating or kneading with various synthetic resins. Depending on the purpose of use, these carriers may be used as emulsifiers, dispersants, suspending agents, wetting agents, stabilizing agents, etc. Adding agents, etc., oil agents, emulsions,
It may be used in the form of wettable powders, powders, tablets, propellants, etc.

The insect repellent and fungicide of the present invention may optionally contain other insecticides,
Insect repellents, fragrances, fungicides, and fungicides may be appropriately mixed and used.

The concentration of active ingredients in the preparation and the application rate depend on the dosage form, prophylaxis,
It can be selected arbitrarily depending on extermination, type of pest, degree of damage caused by pest, type of mold, etc. However, in the case of liquids, powders, etc., the content of alkyl cinnamate is usually about 1 to 10% by weight, more practically about 1 to 5% by weight.

The insect repellent and fungicidal agent of the present invention can contain the active ingredient itself or its preparation in the case of termites, their infestation sites and nests, foundations, pillars, building materials, structures, their soil, electric wires, etc. where termite damage should be prevented. Apply to cable sheathing, etc.
It is applied by means such as spraying, dipping, pouring, scattering, mixing, and kneading. In the case of cockroaches, damage caused by cockroaches can be effectively controlled by killing the insects or causing them to escape from a certain area by spraying, scattering, coating, etc. on the cockroaches' habitats, hiding places, passages, etc. Mites (e.g. woolly mites, white mites, claw mites, lice mites, dust mites,
In the case of house dust mites, Demodex mites, etc., the mites can be killed or repelled by spraying, spraying, coating, etc. on areas where the mites live, such as general households, grain warehouses, cafeteria kitchens, furniture, closets, washrooms, etc. .

Furthermore, other pests such as woolly pests, mosquitoes, gnats,
By employing the same means as described above against pest insects such as fleas and flies, or molds, it is possible to effectively exhibit the insect-proofing and mold-proofing effects.

The present invention will be explained in more detail below based on Examples. For each side below, percentages are by weight unless otherwise specified.
shows.

Example 1 Go Boo A polypropylene resin container measuring 25 cm x 18 cm and 8 cm high (to improve ventilation, the two sides are 4 cm x 4 cm).
At the bottom of a methyl cinnamate tablet (- 0.7 cm of methyl cinnamate per tablet).
0036g mixed with 0.0364g of epoxy resin) in a cardboard box (5cm x 9.5cm)
The hole (opening for cockroaches to enter) of box 0, in which the box (m x 2 cm) and the empty box were placed, was placed so that it faced the opposite direction. A petri dish containing absorbent cotton soaked with water was placed at the bottom of the center of the container. I spread butter on the sides of the container to prevent cockroaches from escaping.

Varying numbers of adult cockroaches (Watata type, distributed from Japan Environmental Health Center) were released into containers, and after covering with lids (made of polyethylene resin, 14 cm x 12 cm cut out and pasted with saran mesh), they were kept at room temperature ( It was placed in a dark place at a temperature of 15-20°C.

After 24 hours, the number of adult cockroaches in each box was determined.

The results are shown in Table 1, and showed an excellent insect repellent effect.

Table 1 Example 2 Methyl cinnamate on floor 1 was dissolved in ether and 1.0% based on P paper.
, 0.5% and 0.1% on filter paper (2 g) and air-dried for 4 hours. Each of these r papers was placed in a Petri dish, 3.5 ml of distilled water was added, and then placed in a thermostatic oven with 30 worker termites and 3 soldier ants and left for 14 days.

The mortality status of termites is shown in Table 2, and methyl cinnamate showed an excellent insecticidal effect.

See Table 2 ml and 0.98 ml of 5% diluted solution, respectively.
Experiment B) to investigate the mortality rate of the woolly mite using the same method as above.

The results are shown in Table 3. In all cases, excellent insecticidal effects were shown.

Example 3 Methyl cinnamate and 1 diluted with denatured alcohol
Transfer the 0% diluted solution and the 5% diluted solution to a circular filter paper (90 g/m2) with a diameter of 5.8 cm and add 0.28 ml of methyl cinnamate (1.10%).
Soak 0.33ml of the diluted solution and 0.33ml of the 1.5% diluted solution, place each of these filter papers on the bottom of a Petri dish, place about 50 woolly mites on the test paper, cover the Petri dish with Japanese paper, and leave at room temperature. The mortality rate was examined by leaving the specimens under conditions of humidity 75% R, H for 24 hours (Experiment A).

0.85 ml of methyl cinnamate, 10% diluted solution 0.98 Table 3 Example 4 Measuring method a Test bacterial strain harmful to food Aspergillus nigerPenicil, commonly found as a fungus
lium cLtrinum Cladosporiu
m cladosp.

ricides Fsarium proliferalumAlt
Ernaria alternata was cultured in a medium at 26° C. for 10 days, stored in a refrigerator, and used after returning to room temperature in the experiment.

b, Medium malt extract C0X0 manufactured by ID > 20 g, peptone (manufactured by Mitani Kagaku Sangyo Co., Ltd. > Ig, glucose (manufactured by Kanto Kagaku Co., Ltd.) 2
0g, agar (manufactured by Nacalai Tesque) 20g and water 10g
After sterilizing 100O in an autoclave at 121℃ for 15 minutes, place it in a Petri dish with a diameter of 6cm for about 10m in a clean bench.
1 was added, and the solidified medium was used as a test plate medium.

In addition, approximately 6 ml of a medium with the same composition was placed in a test tube (inner diameter 1.3 cm, length 16 cm) with a silicon stopper, and the same operation as above was performed to prepare a slant medium for preservation.

C2 Antibacterial activity measurement method 20% methyl cinnamate dissolved in denatured alcohol was
0.2 m in cm circular filter paper (manufactured by Toyo Roshi Co., Ltd., NO12)
One drop was added, and after drying in a clean bench for about 20 minutes, the filter paper was placed on the culture medium in the petri dish. One platinum loop of spores from a preserved strain cultured on a slant medium was placed in 5 ml of a 0.005% sodium laurate aqueous solution, and the mixture was shaken for about 2 minutes to fully suspend the spores, which was used as spore suspension water. For the spores, add 0.2ml of spore suspension directly to the filter paper on a Petri dish medium.
was inoculated and dropped. Then in an incubator at 26℃ for 3
After culturing for several days, the antibacterial properties of methyl cinnamate were determined from the growth state of the mold.

d. Judgment Results The antibacterial activity of methyl cinnamate against each bacterial strain is shown in Table 4. It showed antibacterial activity against all of the bacterial strains. especially,
It showed excellent antibacterial activity against Claciosporium%Fusarium.

Table 4 Note: Antibacterial activity strength order of strength ++++ ++++ ++ 10
- Weak Example 5 Test Method The antibacterial properties of methyl cinnamate against white-knot bacteria were tested according to AATCC test method 90-1982 (halo test).

a. Test strain Trichophyton mentagr.

phytes IFO6124 b, Bacterial enrichment medium 5% blood Sasabro agar medium Eiken Chemical) C8 measurement medium Sabouraud agar medium (Eiken Chemical) d, Preparation of bacterial solution Inoculate the test bacteria into the bacterium enrichment medium and heat at 25°C. After culturing for 10 days, the spores were suspended in a 0.005% dioctyl sodium sulfosuccinate solution at a concentration of about 10'/ml, and this was used as a bacterial solution.

e. Preparation of test plate culture medium The bacterial solution was added and mixed at a ratio of 1 ml to 150 ml of the measurement medium, and this was dispensed into petri dishes in 15 ml portions and solidified to form a test plate medium.

f, Judgment Granular ethylene-vinyl acetate copolymer resin 40 mg/1
Prepare 10 samples by impregnating the particles with 2 mg of methyl cinnamate, place 1, 3, and 5 of these samples in the center of a test plate, seal it, and incubate at 25°C for 14 days.・The presence or absence of an inhibition zone around the sample was determined by visual observation.

g. Test results The results are shown in Table 5.

Table 5 Presence or absence of a growth inhibition zone against white-knot bacteria in samples [Effects of the invention] According to the present invention, a novel insect repellent and anti-mold agent having excellent insecticidal, insect repellent and anti-mold effects is provided.

Claims (1)

[Scope of Claims] An insect repellent or fungicide containing an alkyl cinnamate of the formula ▲ Numerical formula, chemical formula, table, etc. ▼ (in the formula, R represents an alkyl group having 1 to 4 carbon atoms) as an active ingredient