JP2000080007A - Timber insect rest-controlling agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a timber insect pests-controlling agent that can retain its effect for a long period of time and is useful for controlling Isoptera by using a specific cyclopropanecarboxylic ester and a specific phenol as active ingredients. SOLUTION: The objective timber insect pests-controlling agent comprises, as active ingredients, (A) a cyclopropanecarboxylic ester of the formula (R1 and R2 are each methyl or a halogen), typically (S)-2-methyl-4-oxo-3-propyn-2- ylcyclopenten-2-yl (1R)-trans-3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropanecarboxylate or the like and (B) one or more kinds of phenols selected from 2,6-di-tert-butyl-4-methoxyphenol, 2-tert-butyl-4- methoxypnenol and 3-tert-butyl-4-methoxyphenol, preferably at a weight ration of 0.0001-10 pts.wt. of the composition B to 100 pts.wt. of the component A.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a wood pest control agent.

[0002]

Various chemicals have been used to control wood pests such as termites. Generally, in order to control wood pests and protect wood, the chemicals are effective for a long period of time. It needs to be maintained. The present invention
An object of the present invention is to provide a wood pest controlling agent capable of maintaining its efficacy for a long period of time.

[0003]

Under these circumstances, the present inventors have studied a wood pest control agent and, as a result, selected a specific cyclopropanecarboxylic acid ester compound as an active ingredient of the wood pest control agent, By blending one or more phenol compounds selected from the group consisting of 6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol The present inventors have found that the residual effect of the cyclopropanecarboxylic acid ester compound is enhanced and the above-mentioned object is achieved, and the present invention has been accomplished. That is, the present invention relates to the general formula (1) (Wherein, R ¹ and R ² independently represent a methyl group or a halogen atom). A wood pest control agent containing, as an active ingredient, a cyclopropanecarboxylic acid ester compound represented by the following formula (hereinafter, referred to as the present compound). And 2,6-di-
tert-butyl-4-methylphenol (hereinafter, referred to as “compound A”), 2-tert-butyl-4-methoxyphenol (hereinafter, referred to as “compound B”), and 3-tert-
Butyl-4-methoxyphenol (hereinafter, “Compound C”
It is written. The present invention relates to a wood pest control agent comprising one or more phenol compounds selected from the group consisting of:

[0004]

BEST MODE FOR CARRYING OUT THE INVENTION The present compound used as an active ingredient in the present invention includes 2-methyl-4-oxo-3-prop-2-ynylcyclopent-2-enyl
3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate, 2-methyl-4-oxo-3-prop-2-ynylcyclopent-2-enyl 2,2-dimethyl-3 -(2-methylprop-1-enyl) cyclopropanecarboxylate and the like can be mentioned. The present compound has various isomers such as geometric isomers and optical isomers. In the present invention, such isomers can be used alone or in any mixture. As the isomer, for example, (S) -2-methyl-4
-Oxo-3-prop-2-ynylcyclopent-2-
Enyl (1R) cis-trans-2,2-dimethyl-
3- (2-methylprop-1-enyl) cyclopropanecarboxylate (general name: praresulin), (S)-
2-methyl-4-oxo-3-prop-2-ynylcyclopent-2-enyl (1R) -trans-3-
(2,2-Dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate and the like can be mentioned.

On the other hand, compound A, compound B and compound C are known as food additives and additives for plastics. Usually, compound A is used alone, and compound B and compound C are commercially available in the form of a mixture of both. These commercial products can be used as they are.

According to the present invention, a compound A,
By blending at least one phenolic compound selected from the group consisting of compound B and compound C, the residual effect of the present compound as an active ingredient of a wood pest control agent is enhanced. The amount is an amount effective to enhance the residual effect of the compound, specifically, usually 0.0001 to 10 parts by weight, based on 100 parts by weight of the compound,
Preferably, the proportion is 0.2 to 2 parts by weight.

[0007] Wood pests that can be effectively controlled by the present invention include, for example, the termite family (Mastotermiti).
dae), genus Zootermopsis, genus Archotermopsis, Hodotermo
Termites of the genus psis and Porotetmes (Termopsida
e), genus Kalotermes, genus Neotermes, genus Cryptotermes, In
Species of the termite family (Kalotermitidae) such as genus cisitermes and genus Glyptotermes, genus Hodotermes, Microhodotermes
Genus, Anacanthotermes, etc.
otermitidae), Reticulitermes, Heterotermes, C
Optotermes, Schedolinotermes, etc., Rhinotermitidae, Sawtooth (Ser)
ritermitidae), Amitermes, Drepanotermes, Hopi
genus talitermes, Trinervitermes, Macrotermes, Odo
Genus ntotermes, Genus Microtermes, Genus Nasutitermes, Perica
Termites such as genus pritermes and Anoplotermes (Termiti
dae) and other Isoptera pests, Xyleborus sp., Sc
Bark beetle (Scolytidae) such as genus olytoplatypus, Mon
Genus ochamus, Hylotrupes, Hesperophanus, Chloroph
genus orus, genus Palaeocallidium, genus Semanotus, Purpuricen
Cerambycida (Cerambycida) of the genus us and Stromatium
e), the weevil family (Rynchophorida) of the genus Sipalinus
e), Platypodidae such as the genus Crossotarsus and Platypus, Platypodidae such as the genus Lyctus (Lyctidae), genus Dinoderus, genus Bostrychus, Sinoderus
Genus etc., Bostrychidae, Ernobius
Genera, Anobium, Xyletinus, Xestobium, Ptilinus
Genus, Nicobium, Ptilineurus, etc.
biidae), Coleoptera such as Buprestidae (C)
oleoptera pests, Hymenoptera pests such as the wasp family (Siricidae) such as the genus Urocerus and Sirex.

The wood pest controlling agent of the present invention comprises:
Although it may be composed of only one or more phenolic compounds selected from the group consisting of compound A, compound B and compound C, it usually takes the same various formulation forms as general wood pest control agents. Such preparation forms include liquid forms such as emulsions, oils and suspensions, powders, wettable powders, granules, paste preparations, microencapsulated preparations, foams, aerosol preparations and the like. The content of the present compound in the preparation is usually 0.01 to 80% by weight.

[0009] These preparations can be obtained by a usual technique. Carriers and auxiliaries used in the formulation include, for example, the following.

As the solid carrier, for example, clay, talc, diatomaceous earth, pumice, calcite, sepiolite, dolomite, silica,
Natural or synthetic minerals such as alumina, sawdust, corn cobs, coconut husks, fine particles such as tobacco stalks and the like, as liquid carriers, for example, aromatics such as xylene, toluene, alkylnaphthalene Hydrocarbons, halogenated hydrocarbons such as chlorobenzene, methylene chloride, and ethylene dichloride; alcohols such as butanol, glycol, glycol ether, and glycol ester; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; dimethyl sulfoxide , N, N-dimethylformamide and the like.

[0011] Examples of auxiliary agents for pharmaceutical preparations include:
Nonionic emulsifiers such as polyoxyethylene fatty acid esters and polyoxyethylene fatty acid alcohol ethers; ionic emulsifiers such as alkyl sulfonates, alkyl sulfates and aryl sulfonates; dispersants such as lignin sulfonates and methyl cellulose; Fixing agents such as methylcellulose, gum arabic, polyvinyl alcohol, and polyvinyl acetate; coloring agents such as iron oxide, titanium oxide, Prussian blue, alizarin dye, azo dye, and phthalocyanine dye;

The wood pest controlling agent of the present invention comprises a wood pest controlling active ingredient other than the present compound (for example, permethrin,
Cypermethrin, silafluofen, etofenprox, cyphenothrin, fenvalerate, esfenvalerate, tralomethrin, etc.) and synergists.

The wood insect pest control agent of the present invention is usually used by applying it to wood or soil, but it is used in the production of plywood by mixing with an adhesive, and is used in the production of insect-control plywood, or in the case of coated electric wire or wire. By mixing it into a synthetic resin sheet or the like, it can be used for the production of various products that have been treated for insect repellency. When the wood pesticide of the present invention is applied to wood or soil, the compound is applied in an amount of usually about 0.001 to 100 g, preferably about 0.003 to 30 g, per m ^{2 of} wood or soil surface.

[0014]

The present invention will be described below in more detail with reference to examples. First, formulation examples are shown. Example 1 5 parts by weight of praretrin, 0.1 part by weight of Compound A, 10 parts by weight of Solpol SM200 (Emulsifier manufactured by Toho Chemical Co., Ltd.) and 84.9 parts by weight of xylene are well mixed to obtain a wood pest controlling agent (emulsion) of the present invention.

Example 2 5 parts by weight of prarethrin, 0.03 part by weight of compound A, 10 parts by weight of Solpol SM200 (Emulsifier manufactured by Toho Kagaku) and 84.97 parts by weight of xylene are mixed well to obtain the wood pesticide (emulsion) of the present invention. .

Example 3 5 parts by weight of praletrin, 0.1 part by weight of a mixture of compound B and compound C, Solpol SM200 (Emulsifier manufactured by Toho Chemical Co., Ltd.)
10 parts by weight and 84.9 parts by weight of xylene are mixed well to obtain the wood pesticide (emulsion) of the present invention.

Example 4 9: 1 of 0.1 part by weight of pruralethrin, 0.05 part by weight of Compound A, Nisseki Fog Solvent (hydrocarbon solvent manufactured by Nisseki Chemical) and chlorocene Nu (halogenated hydrocarbon solvent manufactured by Dow Chemical Company) ( Volume) mixture to obtain the wood pest control agent (oil) of the present invention.

Example 5 5 parts by weight of praretrin, 0.1 part by weight of compound A, 15 parts by weight of Hisol SAS (hydrocarbon solvent manufactured by Nisseki Chemical), 4 parts by weight of Gohsenol GL-05 (polyvinyl alcohol manufactured by Nippon Synthetic Chemical), Kerzan S (Three crystals; thickener) 0.2 parts by weight, Vegum R (three crystals; thickener) 0.4 parts by weight, Proxel GXL (preservative made by Zeneca) 0.2 parts by weight, propylene glycol 10 parts by weight, TSA-730 (Toshiba Silicone (Antifoaming agent) 0.01 parts by weight and deionized water are mixed to make a total of 100 parts by weight to obtain an aqueous suspension.

Example 6 5 parts by weight of prarethrin, 0.1 part by weight of a mixture of compound B and compound C, 15 parts by weight of Hisol SAS (hydrocarbon solvent manufactured by Nisseki Chemical), 4 parts by weight of Gohsenol GL-05 (polyvinyl manufactured by Nippon Synthetic Chemical) Alcohol), Kerzan S (tricrystal, thickener) 0.2 parts by weight, Vegum R (tricrystal, thickener)
0.4 parts by weight, 0.2 parts by weight of Proxel GXL (preservative made by Zeneca), 10 parts by weight of propylene glycol, 0.01 part by weight of TSA-730 (antifoaming agent made by Toshiba Silicone) and deionized water to make the whole 100 parts by weight. To obtain an aqueous suspension.

Example 7 (S) -2-Methyl-4-oxo-3-prop-2-ynylcyclopent-2-enyl (1R) -trans-
3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate 5 parts by weight, compound A
0.1 parts by weight, Solpol SM200 (Emulsifier manufactured by Toho Chemical) 1
0 parts by weight and 84.9 parts by weight of xylene are mixed well to obtain the wood pesticide (emulsion) of the present invention.

Example 8 (S) -2-Methyl-4-oxo-3-prop-2-ynylcyclopent-2-enyl (1R) -trans-
3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate 5 parts by weight, compound A
0.03 parts by weight, Solpol SM200 (Emulsifier manufactured by Toho Chemical)
10 parts by weight and 84.97 parts by weight of xylene are mixed well to obtain the wood pesticide (emulsion) of the present invention.

Example 9 (S) -2-Methyl-4-oxo-3-prop-2-ynylcyclopent-2-enyl (1R) -trans-
5 parts by weight of 3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate, 0.1 part by weight of a mixture of compound B and compound C, 10 parts by weight of Solpol SM200 (emulsifier manufactured by Toho Chemical) and 84.9 parts by weight of xylene The parts are mixed well to obtain the wood pest control agent (emulsion) of the present invention.

Example 10 (S) -2-Methyl-4-oxo-3-prop-2-ynylcyclopent-2-enyl (1R) -trans-
0.1 parts by weight of 3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate, compound A
0.05 parts by weight and a 9: 1 (volume) mixture of Nisseki Fog Solvent (Nisseki Chemical's hydrocarbon solvent) and Chlorocene Nu (Halogenated Hydrocarbon Solvent from Dow Chemical Co.) are mixed well, and the wood pest of the present invention is mixed. Obtain a control agent (oil).

Example 11 (S) -2-Methyl-4-oxo-3-prop-2-ynylcyclopent-2-enyl (1R) -trans-
3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate 5 parts by weight, compound A
0.1 parts by weight, Hisol SAS (Nisseki Chemical's hydrocarbon solvent) 15 parts by weight, Gohsenol GL-05 4 parts by weight (Nippon Synthetic Chemical's polyvinyl alcohol), Kerzan S (Tricrystal;
0.2 parts by weight of Vegum R (three crystals; thickener) 0.4
Parts by weight, 0.2 parts by weight of Proxel GXL (preservative made by Zeneca), 10 parts by weight of propylene glycol, 0.01 part by weight of TSA-730 (antifoaming agent made by Toshiba Silicone) and deionized water to make the whole 100 parts by weight, An aqueous suspension is obtained.

Example 12 (S) -2-Methyl-4-oxo-3-prop-2-ynylcyclopent-2-enyl (1R) -trans-
5 parts by weight of 3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate, 0.1 part by weight of a mixture of compound B and compound C, 15 parts by weight of Hisol SAS (hydrocarbon solvent manufactured by Nisseki Chemical), Gohsenol GL-05
4 parts by weight (polyvinyl alcohol manufactured by Nippon Synthetic Chemical)
Kelzan S (tricrystal; thickener) 0.2 parts by weight, Vegum R
(Three crystals; thickener) 0.4 parts by weight, Proxel GXL (preservative made by Zeneca) 0.2 parts by weight, propylene glycol 10 parts by weight, TSA-730 (antifoaming agent made by Toshiba Silicone) 0.01 parts by weight and deionized water mixed To 100 parts by weight to obtain an aqueous suspension.

Next, examples of wood pest control tests will be described. Example 13 The emulsion obtained in Example 1 was diluted with water so that the concentration of plaretrin was 0.1% by weight, and 2.5 ml of the obtained diluted solution was mixed with 50 g of soil. About 10 g of the soil was placed in a plastic petri dish (9 cm in diameter), moistened with water, and ten house termites (Coptotermes formosanus) were released, and the mortality (%) after a predetermined time was determined. Table 1 shows the average values of the test results of the three replicates.

[0027]

[Table 1]

Example 14 The emulsion obtained in Example 1 was diluted with water so that the concentration of plaretrin was 0.1% by weight, and the obtained diluted solution was applied on a surface of a synavenia plate in an amount of 100 ml / m ² . After air-drying, a glass ring (4 cm in diameter) was placed on the plywood, and ten house termites (Coptotermes formosanus) were released.
Table 2 shows the average value of the triplicate test after determining the mortality (%) after a predetermined time.

[0029]

[Table 2]

Example 15 The emulsion obtained in Example 2 and the comparative test emulsion obtained according to Example 2 without adding Compound A were diluted with water so that the concentration of plaretrin was 0.05% by weight. 6 ml of the diluted solution thus obtained was sprayed onto 10 g of soil in a plastic petri dish (9 cm in diameter) from a height of about 60 cm at a pressure of 0.8 kg / cm ² . After air drying, the soil was moistened with water, and ten house termites (Coptotermes formosanus) were released. After a predetermined time (30 minutes, 1 hour, 1 day), determine the mortality (%)
Table 3 shows the average value of the three replicate tests. Table 3 also shows the results of a similar test performed on soil that had been stored for one month under dark conditions at 60 ° C. after chemical treatment.

[0031]

[Table 3]

Example 16 The emulsion obtained in Example 2 and the comparative test emulsion obtained according to Example 2 without adding Compound A were diluted with water so that the plaretrin concentration was 0.1% by weight. 6 ml of the diluted solution thus obtained was sprayed onto synavenia (15 × 15 cm) from a height of about 60 cm at a pressure of 0.8 kg / cm ² . After air-drying, a glass ring (4 cm in diameter) was placed on the plywood, and ten house termites (Coptotermes formosanus) were released.
One day later, the mortality rate (%) was determined, and the average of triplicate tests is shown in Table 4. Table 4 also shows the results of similar tests performed using plywood stored at 60 ° C. under dark conditions for 1 and 3 months after the chemical treatment.

[0033]

[Table 4]

Example 17 The emulsion obtained in Example 7 was treated with (S) -2-methyl-4-
Oxo-3-prop-2-ynylcyclopent-2-enyl (1R) -trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate concentration was adjusted to 0.2% by weight. Was diluted with water, and 2.5 ml of the obtained diluted solution was mixed with 50 g of soil. About 10g of the soil
In a plastic petri dish (9 cm in diameter), moistened with water, and then dwarf termites (Coptotermes formosanus) 10
The head was released, and the rate of mortal insects (%) one day later was determined. Table 5 shows the average values of the test results of the three replicates.

[0035]

[Table 5]

[0036]

Industrial Applicability The wood pest controlling agent of the present invention exhibits an excellent controlling effect on various wood pests such as termites and bark beetles.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification FI FI Theme coat ゛ (Reference) A01N 31/08 A01N 31/08 B27K 3/34 BBB B27K 3/34 BBBA F-term (Reference) 2B230 AA04 AA05 BA01 BA03 CB02 CB07 DA02 EB03 4H011 AC03 BA04 BB15 BC03 DA16 DC10

Claims (8)

[Claims] 1. The general formula (1) (Wherein, R ¹ and R ² independently represent a methyl group or a halogen atom). A wood pesticide containing as an active ingredient a cyclopropanecarboxylic acid ester compound represented by the formula: -Tert-butyl-4-methylphenol, 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol, characterized in that at least one phenol compound selected from the group is compounded. Wood pest control agent. 2. A phenol compound as 2,6-di-tert.
The wood pest controlling agent according to claim 1, wherein -butyl-4-methylphenol is used. 3. Cyclopropanecarboxylic acid ester compound
(1) 100 parts by weight of 2,6-di-tert-butyl-
One or more phenol compounds selected from the group consisting of 4-methylphenol, 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol are blended in a ratio of 0.0001 to 10 parts by weight. The wood pest controlling agent according to claim 1. 4. Cyclopropanecarboxylic acid ester compound
(1) 100 parts by weight of 2,6-di-tert-butyl-
The wood pest control agent according to claim 2, wherein 4-methylphenol is blended in a ratio of 0.0001 to 10 parts by weight. 5. A cyclopropanecarboxylic acid ester compound
The substituents R ¹ and R ^{2 in} (1) are a methyl group.
4. The wood pest controlling agent according to any one of 4. 6. Cyclopropanecarboxylic acid ester compound
The wood pest controlling agent according to claim 5, wherein (1) is pleresulin. 7. A cyclopropanecarboxylic acid ester compound
The substituents R ¹ and R ^{2 in} (1) are chlorine atoms.
4. The wood pest controlling agent according to any one of 4. 8. A method for controlling wood pests, which comprises applying the wood pest control agent according to any one of claims 1 to 6 to wood or soil.