JPH06239712A - Controlling agent against soil insect pest - Google Patents

Abstract

PURPOSE:To obtain a controlling agent against soil insect pests comprising a specific carboxylic acid ester having specific excellent performance as an active ingredient. CONSTITUTION:This controlling agent against soil insect pests comprises a carboxylic acid ester of the formula (Y is H or methyl; X is isobutenyl or dihalovinyl when Y is H and methyl when Y is methyl) [e.g. 2-methyl-4- methylidene-3-(2-propynyl)cyclopent-2-enyl 2,2,3,3,- tetramethylcyclopropanecarboxylate] as an active ingredient. Insects such as western corn root worm, northern corn root worm, southern corn root worm, Aulacophora femoralis and Phyllotreta striolata FABRICIUS which are chrysomelids, living in soil and damaging crops are cited as the soil insect pests.

Description

Detailed Description of the Invention

[0001]

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

[0002]

BACKGROUND OF THE INVENTION Pyrethroid compounds are widely used as insecticides because of their low toxicity to mammals, but in general, there is no one having a sufficient controlling effect against soil pests when treated with soil, Only a little tefluthrin has been put to practical use as a soil pest control agent.

[0003]

Generally, it can be said that it is desirable for a soil pest control agent to have various characteristics as described below. That is, the properties that the soil pest control agent should have include, for example: It should be effective against soil pests. 2. Long-term efficacy, that is, residual efficacy. 3. To show repellent action or food damage prevention action. However, the present invention aims to provide a soil pest control agent that satisfies these properties.

[0004]

[Means for Solving the Problems] Under the circumstances, the present inventors have conducted extensive studies to find a compound which is excellent as a soil pest control agent, and as a result, the compound of the general formula

[Chemical 2] [In the formula, Y represents a hydrogen atom or a methyl group, and X is
When Y is a hydrogen atom, an isobutenyl group (2-methyl-1-
A propenyl group) or a 2,2-dihalovinyl group (for example, a 2,2-dichlorovinyl group, a 2,2-difluorovinyl group, a 2-chloro-2-fluorovinyl group, etc.),
When Y is a methyl group, it represents a methyl group. The present invention was completed by discovering that the carboxylic acid ester represented by the formula [4] has specifically excellent performance as a soil pest control agent.

Soil pests that can be controlled by the soil pest control agent of the present invention include, for example, Chrysomelidae, corn root worms, Diabrotica genus Diabrotica virgifera virgifera L.
e Conte (Western Corn Rootworm ), Diabrot
ica barberi Smith and Lawrence (Northern Corn Rootworm , Diabrotica undecimpunctata howardi
Barber (Southern Corn Rootworm ) etc. Aulacophora genus Aulacophora femoralis (Motschuls
ky) (cucurbit leaf beetle), etc. Phyllotreta genus Phyllotreta striolata (Fabriciu
s) (Insect beetle) and other insects that inhabit the soil and damage crops.

The carboxylic acid ester represented by the general formula (2) used as an active ingredient in the present invention can be produced, for example, by the method described in JP-A-56-156238. Examples of the carboxylic acid ester represented by the general formula 2 used as an active ingredient in the present invention include the following compounds. 2-Methyl-4-methylidene-3- (2-propynyl)
Cyclopent-2-enyl 2,2,3,3-tetramethylcyclopropanecarboxylate 2-methyl-4-methylidene-3- (2-propynyl)
Cyclopent-2-enyl chrysanthemate 2-methyl-4-methylidene-3- (2-propynyl)
Cyclopent-2-enyl 3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate 2-methyl-4-methylidene-3- (2-propynyl)
Cyclopent-2-enyl 3- (2,2-difluorovinyl) -2,2-dimethylcyclopropanecarboxylate 2-methyl-4-methylidene-3- (2-propynyl)
Cyclopent-2-enyl 3- (2-chloro-2-fluorovinyl) -2,2-dimethylcyclopropanecarboxylate These carboxylic acid esters have some and / or optical isomers. Isomers and mixtures thereof are also included in the present invention.

When the carboxylic acid ester represented by the general formula 2 is used as an active ingredient of a soil pest control agent, it is usually mixed with a solid carrier, a liquid carrier or a gaseous carrier, and if necessary, a surfactant or other It is used by adding an auxiliary agent for formulation to oil, emulsion, wettable powder, granule, powder, aerosol and the like. In these preparations, the carboxylic acid ester represented by the general formula 2 is used as an active ingredient in a weight ratio of 0.1.
.About.99.9%, preferably 1-80%. Examples of solid carriers include clays (kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, fubasami clay, acid clay, etc.), talcs, and other inorganic minerals (serisite, quartz, sulfur, activated carbon, calcium carbonate, water). (Eg, Japanese silica), chemical fertilizers (ammonium sulphate, ammonium phosphate, ammonium nitrate, urea, ammonium salt, etc.), etc., and fine powders or granules. Examples of liquid carriers include water and alcohols (methanol, ethanol, etc.). , Ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene,
Kerosene, etc.), esters (ethyl acetate, butyl acetate, etc.),
Nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.), acid amides (dimethylformamide, dimethylacetamide, etc.), and the like can be mentioned. For example, CFC gas, butane gas, carbon dioxide gas, etc. may be mentioned. Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylenated products thereof, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives and the like. Can be mentioned. Examples of formulation adjuvants such as sticking agents and dispersants include casein, gelatin, polysaccharides (starch powder, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (polyvinyl alcohol). , Polyvinylpyrrolidone, polyacrylic acids, etc., and examples of stabilizers include PAP (isopropyl acid phosphate), BHT (2,
6-di-tert-butyl-4-methylphenol), BH
A (2-tert-butyl-4-methoxyphenol and 3-
tert-butyl-4-methoxyphenol),
Examples thereof include vegetable oils, mineral oils, surfactants, fatty acids or esters thereof. The preparation thus obtained is sprayed on the surface of the soil as it is or diluted with water or the like, and if necessary, mixed with the soil or irrigated with the soil. Also other pesticides,
Nematicides, acaricides, fungicides, herbicides, plant growth regulators, fertilizers, BT agents, microbial pesticides such as pathogenic virus agents,
It can be used simultaneously with or without mixing with an insect hormone agent and a soil conditioner. When the carboxylic acid ester represented by the general formula 2 is used as the active ingredient of the soil pest control agent, the application amount is usually 1 to 500 g, preferably 5 to 200 g per 10 ares, and the emulsion,
When a wettable powder or the like is diluted with water and applied, the application concentration is 0.5 ppm to 30%, and powders, granules, oils, aerosols and the like are applied as they are without being diluted. These application rates and application temperatures all vary depending on the type of formulation, application time, application site, application method, type of pest, degree of damage, etc., and may be increased or decreased without regard to the above range. can do.
Further, the soil pest control agent of the present invention contains piperonyl butoxide, MGK-264 (N- (2-ethylhexyl) bicyclo [2,2,1]], which is optionally mixed with a known pyrethroid insecticide. Hept-5-ene-2,3-dicarboximide), S-421 (bis- (2,3,3,3
A synergist such as 3-tetrachloropropyl) ether) or a stabilizer such as an organic acid or a phenolic antioxidant can be added. The addition amount of these is usually 1/100 to 10 times the active ingredient compound by weight.

[0008]

EXAMPLES Next, the present invention will be described more specifically by way of examples. The compounds are shown by the compound numbers shown in Table 1.

[Table 1] The compounds used for comparison in Test Examples are shown by the following compound symbols (A) to (D). The compounds listed in Table 2 are disclosed in
55-153742 and JP-A-56-156238.

[Table 2] Tefurfurin (compound (D): 2, 3, which is used as a soil pest control agent among pyrethroid compounds)
5,6-Tetrafluoro-4-methylbenzyl (Z)-
(1RS) -cis-3- (2-chloro-3,3,3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate) was also used as a comparative compound.

First, formulation examples are shown. In addition, a part represents a weight part. Formulation Example 1 Emulsion 20 parts of Compounds (1) to (5) are dissolved in 65 parts of xylene, and emulsifier Solpol 3005X (registered trademark of Toho Kagaku) 1
Add 5 parts and mix well with stirring to obtain 20% emulsion of each. Formulation Example 2 Wettable Powder To 40 parts of Compounds (1) to (5), 5 parts of Solpol 3005X (described above) was added, mixed well, and Carplex # 80
(Shionogi registered trademark, synthetic hydrous silicon oxide fine powder)
Add 32 parts and 23 parts of 300 mesh diatomaceous earth and stir-mix with a juice mixer to obtain each 40% wettable powder. Formulation Example 3 Granules Compounds (1) to (5) 1.5 parts and AGSORBLVM-MS24 /
48 (fired montmorillonite manufactured by OIL DRI, particle size 2
4 to 48 mesh granular carrier) 98.5 parts are added and mixed well to obtain each 1.5% granule. Formulation Example 4 Granules Compounds (1) to (5) 1.5 parts and attapulgite L
98.5 parts of VM24 / 48 (calcined product of attapulgite manufactured by ENGELHALD, granular carrier having a particle size of 24 to 48 mesh) is added and mixed well to obtain each 1.5% granules. Formulation Example 5 Granules Compounds (1) to (5) 1.5 parts and BIODAC25 / 50
(OIL DRI's pulp waste granulation product, particle size 25
˜50 mesh granular carrier) 98.5 parts and well mixed to obtain each 1.5% granules. Formulation Example 6 Granules After thoroughly mixing 1.5 parts of Compounds (1) to (5) and 5 parts of polypropylene glycol (average molecular weight 1000), AGSORBLVM
-Add 93.5 parts of MS24 / 48 (calcined product of montmorillonite manufactured by OIL DRI, granular carrier having a particle size of 24-48 mesh) to obtain 1.5% granules of each. Formulation Example 7 Microcapsules After mixing 10 parts of Compounds (1) to (5), 10 parts of phenylxylylethane and 0.5 part of Sumidule L-75 (tolylene diisocyanate manufactured by Sumitomo Bayer Urethane Co.), gum arabic 20% of 10% aqueous solution and stirred with a homomixer to obtain an emulsion having an average particle size of 20 μm. Then add 2 parts of ethylene glycol to it,
Further, the mixture is reacted in a warm bath of 60 ° C. for 24 hours to obtain a microcapsule chiller. On the other hand, 0.2 parts of xanthan gum and 1.0 part of Veegum R (aluminum magnesium silicate manufactured by Sanyo Kasei) are dispersed in 56.3 parts of ion-exchanged water to obtain a thickener solution. 42.5 parts of the above microcapsule chiller and 57.5 parts of thickener solution are mixed to obtain each 10% microcapsule. Formulation Example 8 Flowable Agent After mixing 10 parts of the compounds (1) to (5) and 10 parts of phenylxylylethane, 10% of polyethylene glycol
Add to 20 parts of the aqueous solution and stir with a homomixer to obtain an emulsion having an average particle size of 3 μm. Meanwhile, Zang Sangam
0.2 part and 1.0 part of Veegum R (aluminum magnesium silicate manufactured by Sanyo Kasei) are dispersed in 58.8 parts of ion-exchanged water to obtain a thickener solution. 40 parts of the above emulsion and 60 parts of the thickener solution are mixed to obtain each 10% flowable agent. Formulation Example 9 Powder 5 parts of Compounds (1) to (5) are added to Carplex # 80 (the above) 3 parts, PAP 0.3 part and 300 mesh talc 9
Add 1.7 parts and stir-mix with a juice mixer to obtain each 5% powder. Formulation Example 10 Oil formulation 0.2 parts of Compounds (1) to (5) are methylnaphthalene 99.8
Dissolve in 1 part to obtain 0.2% oil solution of each.

Next, a test example will be shown. Test Example 1 5 ml of a water-diluted solution of the emulsion of the test compound prepared according to Preparation Example 1 was mixed with 50 g of sterilized soil (16 mesh) to adjust the concentration of the active ingredient in the soil to 1.0 or 0.5 ppm. did. This soil was transferred to a polyethylene cup with a diameter of 5.6 cm and a height of 5.8 cm, and two corn roots of about 2 cm were planted.
Southern corn root worm ( Diabroticaundecimpunctat
a howardi Barber) Ten third-instar larvae were released. Process 3
After a day, the life and death of the larvae and the feeding damage of corn were observed. The degree of feeding damage was judged according to the criteria shown in Table 3.
The results, that is, the mortality rate (%) and feeding damage are shown in Table 4 respectively.
And shown in Table 5.

[Table 3]

[Table 4]

[Table 5] Test Example 2 Emulsion Dilution Solution 5 of Test Compound Prepared According to Formulation Example 1
ml was mixed with 50 g of sterile soil (16 mesh). The concentration of active ingredient in the soil is 4.0ppm, and the treated soil is 25
It was stored under conditions of ℃ and total darkness. One week, two weeks, three weeks, and five weeks after the soil treatment, the treated soil was transferred to a polyethylene cup (diameter 5.6 cm, height 5.8 cm), and two rooted corns were planted to about 2 cm, and Southern Corn root worm ( Diabrotica undecimpunctata howardi Barber) 3
Ten old larvae were released. Three days after the larvae were released, the number of live and dead larvae was examined and the mortality rate (%) was calculated. The results are shown in Table 6
Shown in.

[Table 6]

[0011]

The soil pest control agent of the present invention exhibits an excellent soil pest control effect.

Claims (1)

[Claims] 1. A general formula: ## STR1 ## [In the formula, Y represents a hydrogen atom or a methyl group, and X represents Y.
When is a hydrogen atom, it represents an isobutenyl group or a dihalovinyl group, and when Y is a methyl group, it represents a methyl group. ] The soil pest control agent containing the carboxylic acid ester shown by these as an active ingredient.