JPS63227504A - Agent for promoting insecticidal activity - Google Patents

Abstract

PURPOSE:To obtain an agent effective in remarkably promoting insecticidal activity of various insecticides such as pyrethroidal insecticide, carbamate insecticide and organophosphorus insecticide, by using a specific pyrazole compound as an active component. CONSTITUTION:A compound of formula (R is lower alkyl, halogen, halogenated lower alkyl, NO2, NH2 or lower alkylcarbonylamino; n is 1, 2 or 3; X and Y are halogen) known as a herbicide is used as an active component. A compound containing the active component is compounded to known insecticides such as pyrethroidal insecticide, carbamate insecticide and organophosphorus insecticide at a weight ratio of 1:0.01-100, preferably 1:0.1-10. The insecticidal activity of the above insecticide can be remarkably improved by the combined use of the compound compared with single use to enable the reduction of the amount of the insecticide. Furthermore, the compound is free from phytotoxicity against useful crops and accordingly, the compound is useful as a safely usable agent for promoting insecticidal activity.

Description

[Detailed Description of the Invention] 1) Field of Industrial Use The present invention relates to an efficacy enhancer for pyrethroid insecticides, carbamate insecticides, organophosphorus insecticides, etc. . More specifically, the present invention relates to a pyrethroid insecticide or a carbamate insecticide, which contains a pyrazole compound represented by the general formula (I) below as an active ingredient for enhancing insecticidal efficacy. , relates to efficacy enhancers such as organophosphorus insecticides.

When such insecticidal efficacy enhancers are added to the various insecticides mentioned above, they are useful for controlling agricultural pests, forest pests, horticultural pests, sanitary pests, and the like. therefore,
The present invention can be effectively utilized in the fields of agriculture, horticulture, hygiene, and industry.

(2) Compounds represented by the general formula (I) described later in the present invention were discovered by the present inventors, and they were disclosed in Japanese Patent Application Laid-open No.
It is known to have herbicidal activity in JP-A No. 260065 and JP-A No. 62-33108. However, the physiological effects of these pyrazole compounds are
It is not known other than to have herbicidal activity.

On the other hand, so far, compounds that enhance the efficacy of insecticides include 3,4-methylenedioxy-6-propylbenzylbutyl diethylene glycol ether (piperonyl butoxide), N-(2-ethylhexyl)-bicyclo(2,
2,1) Hebut-5-ene anhydrophthalic acid-2,
3-dicarboximide (MGK-263), 4-(
3,4-methylenedioxyphenyl)-5-methyl-1
゜3-dioxane (safloxane), etc. are known.

Among these compounds, piperonyl butoxide, the most commonly used compound, is effective against certain pyrethroid insecticides, but its potency-enhancing effect may not be sufficient against carbamate insecticides. However, it may not be effective against all insecticides.

Furthermore, due to the extensive use of insecticides, many insect pests have appeared that are resistant to existing insecticides, such as carbamate-based or organic phosphate-based insecticides. Under these circumstances, due to the need to control these pests, methods such as spraying even more effective insecticides than ever before or using them in combination with other insecticides have become necessary. The course is now available. However, spraying large amounts of these insecticides and using them for other purposes not only promotes the emergence of pests with stronger resistance, but also causes chemical damage to crops, toxicity to humans and animals, environmental pollution, and increases in spraying costs. This is not at all desirable.

Under these circumstances, various efforts have been made to develop insecticidal efficacy enhancers, but to date no compound has been found that can enhance the efficacy of existing insecticides when used in small doses.

(3) Problems to be solved by the invention Some conventional insecticidal efficacy enhancers work extremely effectively depending on the type of insecticide used, but they cannot be used effectively for many types of insecticides. Moreover, its enhancement effect is not necessarily satisfactory. Therefore, the development of new insecticidal efficacy enhancers is desired.

The object of the present invention is to provide a new insecticidal efficacy enhancer that meets these needs.

2) Conflict of shame (1) Means for solving the problem In order to deal with the current situation, the present inventors have conducted extensive research using various drugs. As a result, by adding one type of pyrazole compound represented by general formula (I) to various insecticides such as pyrethroid insecticides, carbamate insecticides, and organophosphorus insecticides, insecticides can be Its insecticidal efficacy is significantly increased compared to the effect when used alone,
They discovered that it is highly effective against many pests, and completed the present invention.

therefore. The gist of the present invention is the following general formula (I) (wherein R represents a lower alkyl group, a halogen atom, a halogenated lower alkyl group, a nitro group, an amino group, a lower alkylcarbonylamino group, and n represents an integer from 1 to 3, and X and Y represent the same or different halogen atoms. The present invention provides insecticidal efficacy enhancers such as:

Examples of insecticides whose insecticidal efficacy is enhanced by the compound having the general formula (I) include pyrethroid insecticides, carbamate insecticides, organophosphorus insecticides, and the like.

Representative compounds of these include the following.

That is, examples of pyrethroid insecticides include natural pyrethrin compounds or allethrin, resmethrin, permethrin [(3-phenoxybenzyl (I)
R3)-cis.

trans-3-(2,2-dichlorovinyl)-2,2-
dimethylcyclopropanecarboxylate), fenvalerate, cycloprothrin ((R,S)-α-cyano-3-phenoxybenzyl(R,S)-2,2-dichloro-1-(4-ethoxyphenyl)-cyclo brobancarboxylate] or etofenebrox (
Examples include synthetic pyrethroid compounds such as 2-(p-ethoxyphenyl)-2-methylpro and 3-phenoxybenzyl ether). Carbamate insecticides include NAC, BPMClMTMC, XMC, P
Examples include HC, ethiophenecarb, virimicarb, carbosulfan, methomyl, and the like. In addition, as organic insecticides, MEP, diazinon, acephate, MPP, ECP, isoxathion, pyridafenthione, chlorpyrifos-methyl, chlorpyrifos, ES
P, bamitothione, marathon, PAP, dimethoate,
Ethylthioneton, Phosaron, DDVP, Propaphos,
EPN, etc. can be mentioned. However, the present invention is not limited to these examples.

In addition, the above-mentioned insecticide groups are described in "Pesticide Handbook 1985
This is the common name listed in the 2016 edition of the Japanese Plant Protection Association (Japan Plant Protection Association, published on January 30, 1986).

The compounding ratio of the compound represented by the general formula (I) and an insecticide such as a pyrethroid insecticide, a carbamate insecticide, or an organophosphorus insecticide is 1:0.01 in parts by weight.
~Zoo Preferably, it is in the range of l:O1 to lO. Next, representative examples of the compounds represented by the general formula (I) are shown in Table 1.

Table 1 The compound represented by the general formula (I) of the present invention, when added to pyrethroid insecticides, carbamate insecticides, organophosphorus insecticides, etc., significantly enhances the insecticidal effect of these insecticides. It has a reinforcing effect.

(3) Examples (For the production method and formulation method of the insecticidal efficacy enhancer, the compound represented by the general formula (I) of the present invention is
It is produced by the method described in JP-A-260065 and JP-A-62-33108.

Further, the method of blending the compound represented by the general formula (I) of the present invention with a pyrethroid insecticide, a carbamate insecticide, an organophosphorus insecticide, etc. is not particularly limited. Therefore, by mixing the two in an appropriate manner, adding various carriers such as solids, liquids, gases, etc., surfactants, and other auxiliaries used in the formulation of ordinary insecticides, a powder is prepared according to a conventional method. It can be formulated into various forms such as granules, hydrating tablets, flowable tablets, and aerosols. Alternatively, the compound represented by the general formula (1) of the present invention and the insecticide may be formulated separately by a conventional method, and the two may be mixed at the time of use.

In the above, solid carriers that can be used include mineral powders (kaolin, bentonite, clay montmorillonite, talc, diatomaceous earth, mica, silica sand, ammonium sulfate, urea, etc.), vegetable powders (soybean flour, wheat flour, wood flour, tobacco flour, starch, crystalline cellulose, etc.), alumina, silicates, morning-type coalescence, highly dispersed silicic acid, waxes, etc.

Liquid carriers include water, alcohols (methyl alcohol, ethyl alcohol, n-propyl alcohol, 1so-propyl alcohol, n-butyl alcohol, ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons (benzene, toluene, etc.). , xylene, ethylbenzene, chlorobenzene, cumene, methylnaphthalene, etc.), halogenated hydrocarbons (chloroform, carbon tetrachloride, dichloromethane, chloroethylene, trichlorofluoromethane, dichlorodifluoromethane, etc.), ethers (ethyl ether, ethylene oxide, dioxane, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, methyl isobutyl ketone, etc.), esters (ethyl acetate, butyl acetate, ethylene glycol acetate, amyl acetate, etc.), nitriles (acetonitrile, propionitrile, etc.)
acrylonitrile, etc.), sulfoxides (dimethyl sulfoxide, etc.), alcohol ethers (ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, etc.), aliphatic or alicyclic hydrocarbons (n-hexane, cyclohexane, etc.), industrial gasoline ( (petroleum ether, solvent naphtha, etc.) and petroleum fractions (paraffins, kerosene, light oil, etc.).

Further, examples of the gaseous carrier include liquefied petroleum gas, dimethyl ether, and lower hydrocarbons (butane, propane, etc.).

In addition, surfactants (or emulsifiers) are used for the purposes of emulsification, dispersion, solubilization, wetting, foaming, lubrication, and spreading when preparing formulations such as emulsions, water preparations, and sols (flowable preparations). . Examples of such surfactants include those shown below, but the surfactants are of course not limited to these examples.

Nonionic polyoxyethylene alkyl ether, polyoxyethylene alkyl ester, polyoxyethylene sorbitan alkyl ester, sorbitan alkyl ester, etc.

Anionic alkylbenzene sulfonate, alkyl sulfoxane-1-, alkyl sulfate, polyoxyethylene alkyl sulfate, aryl sulfonate, etc.

Cationic alkylamines (laurylamine, stearyltrimethylammonium chloride, alkyldimethylbenzylammonium chloride, etc.), polyoxyethylene alkylamines, etc.

hermaphrodite Carboxylic acids (betaine type), sulfuric esters, etc.

In addition to these, polyvinyl alcohol (PVA
), lignin sulfonic acid (salt), carboxymethyl cellulose (CMC), gum arabic, polyvinyl acetate, gelatin, casein, sodium alginate, gum tragacanth, and various other adjuvants can be used.

Further, if necessary, a suitable amount of stabilizers such as antioxidants and ultraviolet absorbers may be added.

Next, examples of formulations of insecticidal compositions containing the insecticidal effect enhancer represented by the general formula (I) of the present invention will be given. In addition, all parts simply mentioned in the text mean parts by weight.

Example 1 (Irrigation agent) Compound No. 3, 10 parts, acephate 10 parts,
15 parts of white carbon, 3 parts of calcium lignin sulfonate, 2 parts of polyoxyethylene nonylphenyl ether, 5 parts of diatom and 60 parts of clay are uniformly mixed in a grinding mixer to obtain an irrigation agent.

X1j1ζTechnology 5' low compound positive, 20 parts of compound of l, 5 parts of permethrin, Tsurupol 700H (emulsifier manufactured by Toho Chemical Industry Co., Ltd.)
20 parts and 60 parts of xylene are mixed to obtain an emulsion.

Example 3 (powder) Compound disintegration, 1 part of compound No. 8, 0.5 parts of NAC, 0.5 parts of silicic anhydride fine powder, 0.5 parts of calcium stearate
50 parts of clay and 48.5 parts of talc are uniformly mixed and ground to obtain a powder.

Example 4 (Aerosol) 20 parts of dimethyl ether as a propellant was added to 0.4 parts of compound 11k1.10, 0.2 parts of fenvalate and 79.6 parts of methylene chloride, and the mixture was canned.
Obtain an aerosol.

3) &”J and 1 pot Implementation of the present invention brings about the following effects.

That is, firstly, when one of the compounds represented by the general formula (I) of the present invention is added to pyrethroid insecticides, carbamate insecticides, organophosphorus insecticides, etc., the effects of these insecticides are The insecticidal activity of wood is enhanced, resulting in a strong insecticidal effect. Such effects are seen in various pest insects. Examples include sanitary pests such as the house fly, Culex mosquito, Culex mosquito, and German cockroach; rice crop pests such as the Japanese brown planthopper, brown planthopper, and black leafhopper;
Fruit tree and painting pests such as diamondback moth and peach moth, human body,
These include mites that are parasitic on houses, food, and plants, as well as grain weevils and mealybugs that damage stored grain. Furthermore, similar effects can be expected on other agricultural pests, sanitary pests, forest pests, and horticultural pests.

Second, since the insecticidal efficacy against the various pests mentioned above can be significantly increased compared to when used alone, the amount of insecticide used can be reduced compared to the past.

Thirdly, although the compound of general formula (I) has herbicidal activity,
It does not cause any chemical damage to useful crops.

Therefore, it can be used with confidence. Depending on how it is used, it can also be expected to have a herbicidal effect.

Fourth, compared to piperonyl butoxide, which has been widely used as an insecticidal efficacy enhancer, the same additives are not effective for all insecticides, including pyrethroid insecticides, carbamate insecticides, and organophosphate insecticides. When compared in quantity, depending on the type of compound of general formula (I), a potency-enhancing effect of twice or more is observed.

Therefore, the pyrazole compound of general formula (I) of the present invention is useful as an efficacy enhancer for various insecticides.

Next, the following test examples demonstrate that the compound represented by the general formula (I) of the present invention can be used as an insecticidal efficacy enhancer for pyrethroid insecticides, carbamate insecticides, organophosphorus insecticides, etc. .

Test Example 1 Insecticidal efficacy against compound-resistant house flies A 1 m drop of a diluted drug solution of a predetermined concentration was placed in a glass petri dish with a filter paper of 9 cm in diameter, and ether-anesthetized adult house flies (organophosphorus and carbamate insecticides) were added into the dish. Agricultural house flies in the third dream that have developed resistance to chemicals)
We killed 10 insects at a time and closed the lids. 24 hours after killing insects, the number of dead and living piles was checked to determine the dead and dead rate (%).

This test was conducted in three trials with 10 animals per area treated with the chemical solution, and the average mortality rate was determined. The results are shown in Table 2.

Table 2 Test Example 2 Insecticidal efficacy against the German cockroach A mixture of the compound of general formula (I) and an insecticide (mixing ratio 1:1) and an acetone solution of each single agent were injected into the thorax-abdominal plate of an adult male German cockroach using a microsyringe. 1ILI
was added dropwise, and the mortality rate (%) after 48 hours at 25°C was determined.

The chemical treatment area will be divided into two areas with 10 animals each.
The average mortality rate was calculated. The results are shown in Table 3.

Table 3: Force test against Culex Culex 70c
Example 4: Ten female Culex mosquitoes were released into a glass chamber measuring 70 cm x 70 cm.
Aerosol (fenvalerate 1100p) containing the compound of the present invention or biveronyl butoxide prepared according to
0.5 ml of p) into a glass chamber.
It was sprayed for 0 minutes. During this period, check the number of knockdown peaks at regular intervals, and check the 50% knockdown time ((icT
so (minutes)) was calculated. Furthermore, after 24 hours, the number of living and dead animals was examined, and the mortality rate (%) was determined. The results are shown in Table 4.

Table 4

Claims (1)

[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. , n represents an integer from 1 to 3, x and Y represent the same or different halogen atoms) as an active ingredient.