JP2001199817A - Insect pest control agent and method of controlling insect pest - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an insect pest control agent exhibiting an excellent insect pest controlling effect on several hazardous arthropod by using as a fumigant. SOLUTION: This insect pest control agent is obtained by holding 2,3,5,6- tetrafluoro-4-methoxybenzyl 3-(2,2-dichlorovinyl)-2, 2- dimethylcyclopropanecarboxylate as an active ingredient on a dried plant.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a pesticidal agent and a method for controlling pests.

[0002]

2. Description of the Related Art Various pest control agents have been developed in the past, but at present, sufficient pest control has not yet been achieved, and the development of more excellent pest control agents has been developed. Is desired.

[0003]

Means for Solving the Problems The present inventors have conducted intensive studies in such a situation, and as a result, have found that 2,3,5,6-tetrafluoro-4-methoxybenzyl 3- (2,2-dichlorovinyl) ) It has been found that an excellent pest control effect can be obtained by soaking a pest control agent obtained by holding a dried plant body with -2,2-dimethylcyclopropanecarboxylate as an active ingredient. That is, the present invention relates to 2,3,5,6-tetrafluoro-4-methoxybenzyl 3- (2,2-dichlorovinyl) -2,2-
A pest control agent (hereinafter, referred to as the pest control agent of the present invention) in which dimethylcyclopropanecarboxylate (hereinafter, referred to as the present compound) is retained as an active ingredient in a carrier composed of a dried plant, and the pest control agent. A pest control method for controlling pests by smoldering (hereinafter referred to as the pest control method of the present invention) is provided.

[0004]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. This compound can be produced, for example, by the following method. Formula 1

Embedded image And a carboxylic acid compound or an acid chloride thereof represented by the following formula:

Embedded image A method of producing by reacting with an alcohol compound represented by the formula: The reaction is usually performed in an organic solvent, if necessary, in the presence of a reaction aid. The reaction time is usually from 5 minutes to 72 hours, and the reaction temperature is usually from -8 hours.
The temperature ranges from 0 ° C. to the boiling point of the solvent used in the reaction or 200 ° C. The molar ratio of the carboxylic acid compound represented by the formula 1 or the acid chloride thereof to the alcohol compound represented by the formula 2 is preferably equimolar or a ratio close thereto. Examples of the reaction assistant include tertiary amines such as triethylamine, 4-dimethylaminopyridine, and diisopropylethylamine, dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, diethylazodicarboxylate, and diisopropylazo. Examples include reagents of dicarboxylate and triphenylphosphine. Examples of the solvent include: hydrocarbons such as toluene and hexane; ethers such as diethyl ether and tetrahydrofuran; halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane; amides such as dimethylformamide; ketones such as acetone; Organic sulfurs such as dimethylsulfoxide and the like and mixtures thereof. After completion of the reaction, the compound can be obtained by performing ordinary post-treatment operations such as extraction with an organic solvent and concentration. The compound can be purified by operations such as chromatography and distillation. The carboxylic acid compound represented by the formula 1 can be produced according to the method described in Pestic. Sci. 5, 791 (1974), and the alcohol compound represented by the formula 2 is disclosed in JP-A-4-6694. It can be produced according to the method described in the gazette.

[0005] The present compound has optical isomers based on the presence of an asymmetric carbon, regardless of whether it has the R configuration or the S configuration, as long as it has biological activity.
These optical isomers and mixtures in any proportions thereof are encompassed within the scope of the present compounds. In addition, there are geometric isomers based on the presence of the cyclopropane ring, regardless of whether they are in the trans form or the cis form, as long as they have biological activity, these geometric isomers and any ratios thereof Are included within the scope of this compound.

In the present invention, a dried plant means a plant obtained by drying a plant to a water content of about 10% or less, and any part of the plant can be used as a raw material of the dried plant. Dry plant is usually powder or 1-1
It is used after being crushed to a size of about 0 mm. The pest control agent of the present invention is usually 1) mixing a dried plant and the present compound 2) diluting the compound with a small amount of an organic solvent and impregnating the dried plant 3) adding a surfactant and water to the present compound To form an emulsion,
It can be produced by a method such as mixing with a dried plant. The pesticidal composition of the present invention can be formed into various three-dimensional shapes such as a cone, a triangular pyramid, a cube, a kamaboko, a column, a cuboid, and a sphere. Examples of the molding method include a method in which soluble starch, water and the like are added to a dried plant, kneaded, formed into a desired shape, and dried. In this case, a dried plant body containing the present compound may be formed, or a dried plant body not containing the present compound may be formed, and then the present compound, an organic solvent diluted solution of the present compound or the present compound may be formed. Emulsion or the like can be impregnated or applied. The pest control agent of the present invention may further include charcoal powder obtained by carbonizing hardwood, conifer, coconut palm, etc., onion, potatoes, starch obtained from rice, wheat, cassava and the like.

As a raw material plant of a dried plant, for example,
Thighling plants such as cloves, sandalwood plants such as sandalwood, camphoraceous plants such as katsura, camphor, tabonoki, ginger plants such as yamana, phyllaceae plants such as pichiri, and sweet pine etc. Plants, Pteridophytes such as Toshikimi, Tufted plants such as Ryuuji Uji, Pteridophytes such as wormwood, Maple plants such as Japanese maple, Pinaceae plants such as Touhi, pine, Japanese maple, Ginkgo Such as ginkgo family, rose, plum, etc., rose family, such as wheat, sesame, sesame, etc., cypress, such as Nezuko, Bikushin, cedar, etc.,
Yamanashi, Eiropara, Yanagi, Onoyagi, etc., Onionaceae plants, such as eel, Echinacea, etc. Wigaceous plants, soybean plants such as red ash, etc., Shining plants such as amber linden trees, walnut plants such as squirrels, sesame stagnant plants such as paulownia, and mossy plants such as lions Pinaceae plants, such as roses, birch plants such as birch, birch plants such as birch, spiders, spiders, phytonaceae, pteridophytes, mulberry plants, red flowers Plants, watermelon plants, tangerine plants and the like can be mentioned.
Dry plant bodies obtained from these plants may be used alone or in combination of two or more.

The content of the present compound in the pesticidal composition of the present invention is usually about 0.01 to 10% by weight to achieve a sufficient pest controlling effect. About 0.01 to 50% by weight can be contained. In the present invention, “Ibusu” means that a dried plant containing the present compound, which is located at a place away from the fire source, is heated by the heat of the fire source.

The pests which can be controlled by the pest control agent of the present invention include arthropods such as various harmful insects and mites, and particularly harmful flying pests, ie, Culex pipiens such as Culex pipiens and Culex pipiens, Aedes aegypti ,
Aedes, such as Aedes albopictus, Anopheles, such as Anopheles chinensis, chironomid, housefly, housefly, housefly, such as house fly, blowflies, flies, Drosophila, fly, flies, flies, flies, and flies. And other dipterous insects.

[0010]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the present invention is limited thereto.

Formulation Example 1 2 g of commercially available burning incense (Tsurushi Nanakinko, Tamasatsudo) obtained by finely chopping and mixing sandalwood, sweet pine, clove, Keishi and Ryuen are impregnated with an acetone solution of 1 mg of the present compound. After air-drying, the mixture is mixed well to obtain the pesticidal composition of the present invention. Formulation Example 2 2 g of a commercially available Maca (Maca, Gyokudo) made from turnip tree, soybean paste, is impregnated with an acetone solution of 1 mg of the present compound, air-dried, and then mixed well to thoroughly control the insect pest control agent of the present invention. Get. Formulation Example 3 Turnip wood, 3 g of commercially available incense (mako, Gyokudo) powdered daikyo, 4 g of tabopoki powder, 3 g of starch obtained from rice, add water, knead, and round into balls The compound is impregnated with an acetone solution of 10 mg of the present compound and then air-dried to obtain the pesticidal composition of the present invention.

Formulation Example 4 Emulsion of the present compound [18 mg of the present compound, Hymar BLZ
(Surfactant manufactured by Matsumoto Yushi Pharmaceutical) 3 mg, Hymar 10
0.25 mg of 02Z (a surfactant manufactured by Matsumoto Yushi Pharmaceutical Co., Ltd.) and 2.8 of Solvesso 150 (an organic solvent manufactured by Exxon Chemical)
24.05 mg of turnip tree, 3 g of commercially available incense powder (maka, Gyokudo), 4 g of tabopoki powder, and 3 g of rice starch obtained by adding water. It is kneaded, molded into a cone, and air-dried to obtain the pesticidal composition of the present invention. Formulation Example 5 Turnip tree, 3 g of commercially available incense powder (maka, Gyokudo), powdered oyster powder 4 g, starch 3 g obtained from rice, charcoal powder carbonized with coconut palm 0.5 g, kneaded with water and molded into a rectangular parallelepiped.
g of acetone solution and then air-dried to obtain the pesticidal composition of the present invention. Formulation Example 6 5 g of wormwood powder, 5 g of sandalwood chopped to about 1 to 5 mm, and 5 mg of an acetone solution of the present compound are combined, air-dried, and mixed well to obtain the pesticidal composition of the present invention.

Formulation Example 7 An emulsion of the present compound [18 mg of the present compound, 50 g of a commercially available burning incense (Tsurushi Nanakinko, Tamasatsudo) obtained by finely chopping sandalwood, sweet pine, clove, Keishi, and dragon brain Hymar BLZ (Matsumoto Yushi Pharmaceutical surfactant) 3 mg, Hymar 1002
0.25 mg of Z (Matsumoto Yushi Pharmaceutical surfactant) and 2.8 mg of Solvesso 150 (Exxon Chemical's organic solvent)
Consisting of 24.05 mg and air-dried,
Mix well to obtain the pest control agent of the present invention. Formulation Example 8 10 mg of the present compound was added to kerosene (JIS) in a mixture of 5 g of dried maple dead leaves finely pulverized, 2.5 g of carbon powder obtained by carbonizing coconut palm, and 2.5 g of dried cedar wood powder.
(No. 1 standard kerosene) and impregnated to obtain the pest control agent of the present invention.

Reference Production Example 1 A mixed solution of 1.0 g of 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl alcohol, 0.42 g of pyridine and 10 ml of tetrahydrofuran was added under ice cooling to a solution of 3 g.
-(2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylic acid chloride {ratio of stereoisomers (1R) -trans form: (1R) -cis form: (1S)-
Trans form: (1S) -cis form = 93.9: 2.5:
3.5: After adding 0.1０0.90 g, the mixture was heated to room temperature and stirred at the same temperature for 8 hours. The reaction solution was added to ice water
and extracted twice with 80 ml of ethyl acetate.
The combined ethyl acetate layers were washed with brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (developing solvent: hexane / ethyl acetate = 20: 1). And 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 3
1.40 g (84% yield) of-(2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylate (hereinafter, referred to as the present compound A) was obtained. ¹ H-NMR (CDCl ₃ , TMS internal standard) δ value (pp
m): 1.13 (s, 3H), 1.26 (s, 3H), 1.3
8 (d, 1H), 1.69 (brs, 6H), 2.10
(Dd, 1H), 3.40 (s, 3H), 4.59
(S, 2H), 4.87 (d, 1H), 5.24 (d
d, 2H)

Test Example 1 2 g of commercially available burning incense (Tsurushi Nanakinko, Tamasatsudo) obtained by finely chopping and mixing sandalwood, sweet pine, clove, Keishi and Ryuen were prepared in Reference Production Example 1. The compound was impregnated with an acetone solution of 1 mg of the present compound A, air-dried, and mixed well to prepare a pest control agent 1 of the present invention. Control insect pest control 1 was prepared in the same manner except that 1 mg of the present compound A was replaced with 1 mg of prarethrin (Sumitomo Chemical Industries, Ltd.). 50
In a ml beaker, 4.5 g of ash was spread, and both ends were lit. 2.4 g of columnar charcoal having a diameter of about 1.4 cm and a length of about 2 cm was lit.
Was placed on the ash. This beaker was placed at the center of the floor in a cubic glass chamber (volume 0.34 m ³ ) of 70 cm on a side, and 2 g of the pesticide 1 of the present invention or the control pesticide 1 was placed in each beaker. Immediately thereafter, 10 adult Culex pipiens (Culex pipiens pallens) were released into the chamber, and the number of insects knocked down successively until 30 minutes later was counted. The KT ₅₀ value (50%
The time required for the insect to knockdown) was determined (2 replicates each). Table 1 shows the results.

[0016]

[Table 1]

Test Example 2 2 g of a commercially available Maca (Maca, Tamawado) obtained by turning off turnip wood, soybean paste, was impregnated with an acetone solution of 1 mg of the present compound A prepared in Reference Preparation Example 1, and air-dried. Thereafter, they were mixed well to prepare the insect pest control agent 2 of the present invention. A control insect pest control 2 was prepared in the same manner except that 1 mg of the present compound A was replaced with 1 mg of praretrin (Sumitomo Chemical Industries, Ltd.). 4.5 g of ash in a 50 ml beaker
Laid on each side, lit at both ends about 1.4cm in diameter, about 2cm in length
2.4 g of columnar charcoal of 2.4 cm was placed on the ash. The beaker was placed at the center of the floor in a cubic glass chamber (volume 0.34 m ³ ) of 70 cm on a side, and 2 g of the pesticide 2 of the present invention or the control pesticide 2 was placed in each beaker. Immediately thereafter, the adult Culex pipiens (Culex pipiens)
pallens) were released into the chamber, and the number of insects knocked down continuously over 30 minutes was counted. From the results obtained, the KT ₅₀ value (the time required for 50% of the insects to knock down) was determined (each replicate). Table 2 shows the results.

[0018]

[Table 2]

[0019]

The pest control agent of the present invention exerts an excellent pest control effect on various harmful arthropods when used by spraying it.

Claims (2)

[Claims] (1) 2,3,5,6-tetrafluoro-4-methoxybenzyl 3- (2,2-dichlorovinyl)-
A pest control agent comprising 2,2-dimethylcyclopropanecarboxylate as an active ingredient held in a dried plant. 2. A method for controlling pests, wherein the pest control agent according to claim 1 is used to control pests.