JPH024203B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to an acaricide. There are many types of mites, such as citrus spider mites and red-spotted spider mites, which parasitize plants and cause great damage to agricultural crops, and house dust mites, black-spotted mites, etc. which parasitize animals and transmit infectious diseases. Although many proposals have been made as control agents for these mites, the development of new mite control agents is desired due to problems such as insufficient control effects or development of drug resistance. On the other hand, due to changes in the living environment in recent years, dust mites, dust mites, etc. have been occurring inside homes, causing problems such as not only causing discomfort but also causing allergic asthma. It has been demanded. In view of the above-mentioned current situation, the present inventors conducted various studies and, as a result, discovered that a specific maleimide derivative represented by the following general formula () exhibits an excellent acaricidal effect, and achieved the present invention. That is, the gist of the present invention is that the general formula (In the formula, X and Y may be the same or different and represent a halogen atom. R represents an alkyl group having 9 to 12 carbon atoms.) A miticide containing a maleimide derivative represented by the following as an active ingredient. The acaricide of the present invention exhibits an extremely excellent acaricidal effect by containing a specific maleimide derivative represented by the above general formula () as an active ingredient. The target mites include spider mites such as orange spider mite, apple spider mite, two-spotted spider mite, false red spider mite, plant parasitic mites such as red mite,
Animal-parasitic mites such as house dust mites and house dust mites,
Further examples include mites, dust mites, and the like. In the general formula (), X and Y are chlorine atom, bromine atom, fluorine atom, or iodine atom, and R is a linear chain having 9 to 12 carbon atoms, which is the active ingredient of the acaricide of the present invention. Or a compound which is an alkyl group having a branched chain can be mentioned. Specifically, N-nonyl-2,3-dibromaleimide, N
-decyl-2,3-dibromaleimide, N-undecyl-2,3-dibromaleimide, N-dodecyl-2,3-dibromaleimide, N-nonyl-2,3-difluoromaleimide, N-decyl- 2,3-difluoromaleimide, N-undecyl-2,3-difluoromaleimide, N-dodecyl-2,3-difluoromaleimide, N-nonyl-2,3-diiodomaleimide, N-decyl-
2,3-diiodomaleimide, N-undecyl-
2,3-diiodomaleimide, N-dodecyl-
2,3-diiodomaleimide, N-nonyl-2-
Chlor-3-iodomaleimide, N-decyl-2
-Chlor-3-iodomaleimide, N-undecyl-2-chloro-3-iodomaleimide, N-nonyl-2,3-dichloromaleimide, N-decyl-2,3-dichloromaleimide, N-undecyl-2 , 3-dichloromaleimide, N-dodecyl-
2,3-dichloromaleimide, N-nonyl-2-
Bromo-3-chloromaleimide, N-decyl-2
-Bromo-3-chlormaleimide, N-undecyl-2-bromo-3-chlormaleimide, N-dodecyl-2-bromo-3-chlormaleimide, N
-nonyl-2-iodo-3-fluoromaleimide, N-decyl-2-iodo-3-fluoromaleimide, N-undecyl-2-iodo-3-fluoromaleimide, N-dodecyl-2-iodo-3
-Fluoromaleimide, N-nonyl-2-bromo-3-iodomaleimide, N-decyl-2-bromo-3-iodomaleimide, N-undecyl-2
-Bromo-3-iodomaleimide, N-dodecyl-2-bromo-3-iodomaleimide, N-nonyl-2-fluoro-3-bromaleimide, N-
decyl-2-fluoro-3-bromaleimide,
N-undecyl-2-fluoro-3-bromaleimide, N-dodecyl-2-fluoro-3-bromaleimide, N-nonyl-2-chloro-3-fluoromaleimide, N-decyl-2-chloro-3
-Fluoromaleimide, N-undecyl-2-chloro-3-fluoromaleimide, N-dodecyl-
2-chloro-3-fluoromaleimide is mentioned. Particularly preferred are compounds in which X and Y are both chlorine atoms or bromine atoms, and compounds in which R is an alkyl group having 9 to 12 carbon atoms. These compounds are e.g.

Maleic anhydride represented by the formula and amines represented by RNH ₂ can be produced by reaction. The acaricide of the present invention can be applied using the above-mentioned active ingredient compound as it is, but it is usually preferably prepared in various forms depending on the purpose of use, such as emulsions, suspensions, and aqueous solutions, using suitable carriers and other compounding agents. , used as wettable powders, powders, oils, aerosols, etc. Examples of liquid carriers include water, alcohols (methyl alcohol, ethyl alcohol, ethylene glycol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), ethers (ethyl ether, dioxane, cellosolves, etc.), and aliphatic hydrocarbons. (gasoline, kerosene,
kerosene, fuel oil, etc.), aromatic hydrocarbons (benzene,
toluene, xylene, solvent naphtha, methylnaphthalene, etc.) halogenated hydrocarbons (dichloromethane, trichlorobenzene, carbon tetrachloride, etc.),
Solvents such as acid amides (dimethylformamide, etc.), esters (ethyl acetate, butyl acetate, glycerin ester of fatty acids, etc.), nitriles (acetonitrile, etc.) are suitable, and one or more of these A mixture of is used. In addition, examples of solid carriers include clays (kaolin, bentonite, etc.), talcs (talcum powder,
Suitable materials are silica (diatomaceous earth, mica powder, etc.), lime, alumina powder, sulfur powder, activated carbon, vegetable powder, etc., and one or a mixture of two or more of these powders are suitable. be done. Suitable compounding agents include emulsifiers, dispersants, spreaders, penetrants, surfactants, stabilizers, etc., and one or a mixture of two or more of these may be used.
Examples of surfactants include nonionic surfactants (polyoxyethylene alkyl allyl ether, polyoxyethylene sorbitan monolaurate, etc.), cationic surfactants (alkyldimethylbenzylammonium chloride, alkylpyridinium chloride, etc.), and anionic surfactants. Examples include surfactants (alkylbenzenesulfonates, ligninsulfonates, higher alcohol sulfates, etc.) and amphoteric surfactants (alkyldimethylbetaine, dodecylaminoethylglycine, etc.). Alternatively, other acaricides, efficacy enhancers, antioxidants, insecticides, rodent repellents and repellents that are not likely to inhibit the activity of the active ingredient of the present invention,
A fungicide, a fungicide, a herbicide, a fertilizer, a flavoring agent, a coloring agent, etc. may be added. The amount of active ingredient in the mite control agent of the present invention and its usage amount are appropriately determined depending on the dosage form, target, application method, application location, etc. For example, when used as an acaricide for agriculture and horticulture, such as for controlling orange spider mites, the amount of active ingredient used is 1 to 1000 g, preferably 10 to 100 g, per 10 ares. In addition, for exterminating indoor mites such as mites, for example, 0.01mg or more per 1 ^m2 , preferably 0.05~
An amount of 50 mg is used. EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples unless the gist thereof is exceeded. The experiments were conducted using the compounds shown in Table 1. The test compound numbers in each example correspond to the compound numbers in Table 1.

[Table] Example 1 (Control test against two-spotted spider mites) 100 mg of the test compound shown in Table 2 was mixed with 5 ml of acetone.
Solpol 3005× (surfactant,
95 ml of a 200 ppm aqueous solution (manufactured by Toho Chemical Co., Ltd.) was added to obtain 100 ml of a solution with an active ingredient concentration of 1000 ppm. Thirty two-spotted spider mites were inoculated onto kidney bean leaves, and the leaves were immersed for about 5 seconds in the chemical solution prepared as described above.
After soaking, the green bean petiole was placed in a test tube filled with water, the leaf was fixed, and the number of surviving mites was investigated after 24 hours and 5 days, and the mite killing rate was determined according to the following formula. The test was repeated twice for each test compound, and the average acaricidal rate is shown in Table 2. Acaricidal rate (%) = 30 - number of living mites / 30 x 100

[Table] Example 2 Test compound in a 9cm x 6cm Koshidakashare
Add 4g of straw treated with 75mg and after humidifying for 2 days,
Add 50 woolly mites, cover, and leave for 24 hours.
After 72 hours, the number of survivors was determined by the heat expulsion method, and the acaricidal rate was calculated according to the formula below. The results are shown in Table 3. Mite killing rate = 50 - number of surviving mites / 50 x 100

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【table】

Claims (1)

[Claims] 1. General formula (In the formula, X and Y may be the same or different and represent a halogen atom. R represents an alkyl group having 9 to 12 carbon atoms.) A miticide containing a maleimide derivative represented by the following as an active ingredient.