JPS6310922B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula The present invention relates to an insect repellent containing a trihaloallyl derivative having the formula (wherein R represents a lower alkyl group) as an active ingredient. In Japanese Patent Publication No. 53-20006, alkyl-2,3,
3-triiodoallyl ether has been disclosed and is known to have antibacterial properties. However, nothing has been said about the control efficacy of these compounds against termites, which are important wood pests, or the repellency efficacy against sanitary pests such as cockroaches and mosquitoes. Hitherto, the damage caused by termites to wood, wooden buildings, and general organic industrial materials has been enormous, and various insecticides have been used in appropriate ways to combat this problem.
These include organic chlorine compounds and inorganic fixation compounds, but these insecticides are highly toxic to humans and livestock, so they are not only problematic when handled, but also become a source of pollution, so their use has recently become less popular. , has come to be seen as a problem. The present inventors have discovered that a compound having the general formula () has an insect repellent effect on wood pests such as termites,
It was found to be useful as a termiticide. In addition, due to the spread of heating equipment in general households and reinforced concrete buildings in recent years, the distribution area and population of cockroaches has tended to expand significantly, and mosquitoes are also often found not only in tropical regions but also in cold regions. and have harmful effects on animals. Therefore, effective pest control measures are important from a sanitary standpoint, but the general formula ()
It has been found that a compound having the following properties has an excellent repellent effect against pests, and is particularly useful as a repellent for sanitary pests such as cockroaches and mosquitoes. Therefore, in the present invention, the term insect repellent is used as a concept that includes the above-mentioned termiticides and pest repellents. Examples of compounds having the general formula () used in the insect repellent of the present invention are as follows. (The compound number is referred to in the following description.) Compound number Compound name 1 3-methoxy-1,1,2-triiodo-1-propene 2 3-ethoxy-1,1,2-triiodo-1- Propene 3 3-n-propoxy-1,1,2-
Triiodo-1-propene 4 3-i-propoxy-1,1,2-
Triiodo-1-propene 5 3-n-butoxy-1,1,2-triiodo-1-propene The compound of the above general formula () can be used as an insect repellent by mixing with a carrier and other adjuvants if necessary. Commonly used formulation forms, such as oil-soluble agents, emulsions,
It is prepared and used in pastes, powders, wettable powders, aerosols, paints, etc. Suitable carriers include inert solid carriers such as clay, talc, bentonite, kaolin, silicic anhydride, calcium carbonate, wood flour; kerosene, ligroin,
Examples include liquid carriers such as xylene, methylnaphthalene, dimethylformamide, and dimethyl sulfoxide; gas carriers such as nitrogen gas, dimethyl ether, chlorofluorocarbon gas, and vinyl chloride monomer. Examples of adjuvants that can be used as appropriate to improve the properties of the preparation and enhance its insect repellent effect include anionic, cationic, and nonionic surfactants, methyl cellulose, vinyl acetate resin, and sodium alginate. Examples include polymeric compounds such as Of course, 2-(4-thiazolyl)benzimidazole; N,N-dimethyl-N'-dichlorofluoromethylthio-N'-phenyl-sulfamide;
4-chlorophenyl-3'-iodopropargyl formal; halogenated phenolic compounds such as trichlorophenol and tribromophenol;
Trialkyltin or triaryltin compounds such as bistributyltin oxide, tributyltin phthalate, or triphenyltin hydroxide; metal salts of N-nitroso-N-cyclohexylamine such as aluminum salts; xyligen-B;
Alternatively, preservatives such as benzanilide compounds, organophosphorus compounds such as phoxim; pyrethroid compounds such as permethrin; carbamate compounds such as bigon; insecticides such as organochlorine compounds such as chlordane; and synergistic agents. agents, repellents of other species,
It can be used in combination with fragrances and the like. In actual use, the content of the compound of the present invention may vary over a wide range depending on the form of the preparation or the purpose of use, but generally a range of 0.01 to 95%, preferably 0.5 to 70% by weight is appropriate. In addition, insect repellents can be used on raw materials such as wood and wood materials by dipping, coating, spraying, or injecting them, or they can be mixed with adhesives and used on plywood, hardboard, etc. It can also be processed into particle board, etc. Furthermore, spraying or coating directly on cockroaches and mosquito habitats, hiding places, passages, etc., placing paper strips, cloth strips, microcapsules, rod-shaped molded bodies containing the compound of the present invention, pasting tape, etc. The method can also be used to treat the entire area where pest infestation is desired. Furthermore, it can be applied to the skin of humans and animals as a lotion or cream to combat mosquitoes, and can also be used as a chemical treatment for clothing and packaging materials. Next, the efficacy of the insect repellent of the present invention will be explained using test examples. Test Example 1 Anti-termite Efficacy Test In an indoor anti-termite efficacy test against termites, a test specimen (Hemlock sapwood, diameter 6.5 mm, thickness 0.2 mm) was added to a 2.0 W/V% acetone solution of the compound of the present invention for 50 minutes.
After soaking for seconds and removing excess solvent with paper,
Air dried for 24 hours. This test specimen was placed in a small sample bottle (inner diameter 1.6 cm, height 2.6 cm), 10 worker ants were placed in it, and it was placed in a dark place at 27℃ and a relative temperature of 95% or higher.
Feeding damage was observed for a week. The results are shown in Table 1. The labeling to indicate the degree of anti-termite efficacy is as follows. +: The test specimen does not suffer from feeding damage at all. ±: The test specimen suffered from feeding damage to the extent of traces. −: The test specimen clearly suffered from feeding damage. In addition, in the untreated test, more than 4/5 of the test specimens disappeared due to feeding damage.

[Table] Test Example 2 Repellent efficacy test against cockroaches The compound of the present invention was applied to the inner bottom surface (9 x 5 cm ² ) of a shelter made of Mino Hoshi (9 x 5 x 1 cm ³ ).
Apply 0.5ml of 2.0W/V% acetone solution evenly,
After air drying, it was placed in the ^center of a 20 x 22 x height 30 cm glass container, and five large black cockroach larvae were added into the container, and the repellent effect was examined from the behavior of the cockroaches for 24 hours after introduction. Ta. The results are shown in Table 2. In addition, the display indicating the repellent effect was as follows. +: Cockroaches do not sneak into the shelter at all. ±: Traces of cockroaches temporarily infiltrating the shelter are observed. −: One or more cockroaches always sneaked into the shelter.

[Table] Next, some formulation examples of the insect repellent of the present invention will be given, but it goes without saying that the blending amount, type of auxiliary agent, etc. can be varied considerably. (In the text, all parts simply refer to parts by weight.) Formulation Example 1 Emulsion 10 parts of Compound No. 1 were dissolved in 40 parts of dimethylformamide, and 50 parts of xylene and 10 parts of polyoxyethylene nonyl phenyl ether were added. The mixture was added and thoroughly mixed to obtain an emulsion. This emulsion can be diluted with an appropriate amount of water and used by coating, dipping, or spraying on wood materials to be treated, and can also be applied to the treatment of plywood, particle board, hardboard, etc. with adhesives. Furthermore, it can be applied to entire areas where pests do not want to live. Formulation Example 2 Oil Soluble Agent 2 parts of Compound No. 2 was dissolved in 2 parts of dimethylformamide, and 96 parts of solvent naphtha was added to obtain an oil agent. This oil is used by spraying, coating, dipping, injecting, etc. on raw materials such as wood materials to be treated and habitats of cockroaches, mosquitoes, etc. Formulation Example 3 Powder 2 parts of Compound No. 3 were dissolved in 10 parts of acetone, 68 parts of clay and 30 parts of talc were added and mixed uniformly, and the acetone was removed by evaporation to obtain a powder. Formulation example 4 Wettable powders 40 parts of Compound No. 1, 56 parts of clay, 3 parts of sodium lauryl alcohol sulfonate, and 1 part of polyvinyl alcohol were mixed uniformly in a mixer, and ground in a hammer mill to form a wettable powder. Obtained. Formulation example 5 Paint 10 parts of compound No. 2, 20 parts of Palite powder,
A paint was obtained by uniformly mixing 10 parts of vinyl resin, 25 parts of pine resin, and 35 parts of xylene. Formulation Example 6 Aerosol 2 parts of Compound No. 1 and 0.5 parts of fragrance were dissolved in 40 parts of deodorized kerosene, filled into an aerosol container, and after a valve was attached, 58 parts of liquefied petroleum gas was pressurized and filled to obtain an aerosol. .

Claims (1)

[Claims] 1 formula An insect repellent containing a trihaloallyl derivative having the formula (wherein R represents a lower alkyl group) as an active ingredient.