JPH041180A - Controlling agent for acarid of cheyletoidae - Google Patents

Abstract

PURPOSE:To obtain a controlling agent for acarid of Cheyletoidae grown in a house, containing specific pyrazoles as active ingredients. CONSTITUTION:The aimed controlling agent containing pyrazoles expressed by formula I (R is 1-6C alkyl, trifluoromethyl or 1-3C alkoxy) as active ingredients. The aimed controlling agent is normally preferably used at a preparation concentration of 0.01-10wt.% in the case of a form of oil, powder m aerosol and at the concentration of 0.1-50wt.% in the case of a form of emulsion, hydrate or aqueous solution. The compound expressed by formula I is produced by reacting a compound expressed by formula II (Z is Cl or Br) with a compound expressed by formula III in a solvent such as benzene or DMF at 0-5 deg.C in the presence of a base.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a control agent that targets tick mites that occur inside houses.

[In addition to conventional techniques, there is strong public interest in measures to control mites, as they can cause allergic asthma, insect bites, and skin sores.

As a method of controlling this pest, it is possible to heat-treat tatami mats, carpets, etc., but in reality, this is not easy to implement due to equipment and labor issues, so chemical agents are used to prevent the pest.

Conventionally, these indoor dust mites have been controlled using drugs used to exterminate harmful insects, such as organophosphorus compounds such as fenitrothion, fenthion, diazinon, and dichlorvos, carbamate compounds such as propoxur and carbaryl, or resmethrin, Pyrethroid compounds such as permethrin and phenothrin are used.

[Problem to be solved by the invention 1 However, mites are organisms that are different from insects in terms of morphology and ring-stopping, and agents that exterminate insects are not immediately effective as acaricides, and even if they are effective, Even so, it is known that an incomparably large amount of chemicals is required compared to insect control.

Also, what is effective against some types of mites may be less effective against other types of mites. For example, organic phosphorus compounds and carbamate compounds are generally highly effective against mites, but less effective against house dust mites. However, even though it is an organic phosphorus compound, diazinon has the characteristic that it is highly effective against house dust mites, but is less effective against white dust mites. Furthermore, pyrethroid compounds tend to be more effective against house dust mites than against white mites.

On the other hand, JP-A-64-25763 discloses that certain pyrazole compounds have excellent acaricidal activity. However, the acaricidal activity described in the same publication was evaluated against agricultural and horticultural mites such as spider mites and Ixodes mites, and each showed high activity; There was no description or suggestion of the effect on indoor dust mites, and like other acaricides, the effect on indoor dust mites was completely unpredictable.

Now, among indoor dust mites, most of the ones that occur on a daily basis are house dust mites and dust mites, which are known to cause allergic asthma. The purpose of controlling warts can be achieved by appropriately selecting and using a large amount of insecticides.

On the other hand, tick mites feed on house dust mites and white mites, and when these are lacking, they become biting towards humans. If the habitat is favorable, tick mites appear frequently, and as mentioned above, they bite and cause severe persistent itching and skin eruptions, causing long-term discomfort.However, until now, there are no effective methods for controlling tick mites. Very few highly effective drugs were known, and there was no known reliable method to exterminate ticks other than killing them by heating them to 60 to 100 degrees Celsius with hot air or high-frequency electricity.

[Means for Solving the Problems] The present inventors have investigated drugs that are effective in controlling tick mites and are safe to handle, and have found that a specific pyrazole compound meets the above requirements. They have found that the results are satisfactory and have completed the present invention.

That is, the gist of the present invention is as follows - Shipura [11 (in the above formula, R
represents an 01-C6 alkyl group, a trifluoromethyl group, or an 01-C3 alkoxy group. ) The present invention relates to a pest control agent for ticks, characterized by containing a pyrazole represented by the following as an active ingredient.

Hereinafter, the present invention will be explained in detail.

R in the formula [I] above includes a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an S
- C1 to C6 straight or branched alkyl group such as butyl group, t-butyl group, n-pentyl group, n-hexyl group;
Trifluoromethyl group; or C1 to C3 such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, etc.
straight-chain or branched-chain alkoxy groups.

In addition, the compound represented by the above-mentioned - Funazo [I] is
It is a known compound described in Publication No. 4-25763, and the same publication also indicates that it can be used as an insecticide and acaricide for agricultural and horticultural purposes. Therefore, the compound of formula [I] can be easily synthesized by the method described in the same publication.

For example, it can be easily synthesized according to the reaction formula below.

[II] [I] (In the above reaction formula, 2 represents a chlorine atom, a bromine atom, a hydroxylmethoxy group, an ethoxy group, or a propoxy group.) In the above - Shipura [II], 2 represents a chlorine atom, a bromine atom, Where indicated, aromatic hydrocarbons such as benzene, toluene or xylene; ketones such as acetone, methyl ethyl ketone or methyl isobutyl ketone; halogenated hydrocarbons such as chloroform or methylene chloride; water; esters such as methyl acetate or ethyl acetate. - in the presence of a base at 0 to 30°C, preferably 0 to 5°C, in an aprotic polar solvent such as tetrahydrofuran, acetonitrile, dioxane, N,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide. By reacting Funazo [III], the above-mentioned compound of Funazo [II] can be obtained.

Examples of the base include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, pyridine, and triethylamine.

In addition, in -Funazo [II], when Z represents a hydroxyl group, methoxy group, ethoxy group or propoxy group, solvent-free or N,N-dimethylformamide, N-
In a high boiling point solvent such as methylpyrrolidone or dimethyl sulfoxide, at 150-250°C, preferably at 200-250°C.
By reacting the compound of -Funazo [Ill] with C, the compound of -Funazo [II] can be obtained.

In addition, the compound represented by -Shinzo [H] above is, for example, B
ull, Soc, Chim, France, 2
93 (1966).

When the compound represented by the general formula [II of the present invention is used as a tick repellent, it can be used as it is without adding any other ingredients, but it is usually used in combination with other solvents, carriers, surfactants, etc. It is used in various forms in combination with adjuvants.

Such formulations can be prepared by any conventionally known method and, if necessary, conventionally known dispersants, diluents, thickeners, stabilizers, propellants, and antifoaming agents. etc. are mixed.

Examples of diluents or carriers for liquid preparations include water, alcohols such as methanol, ethanol, isopropanol, ethylene glycol, and propylene glycol, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, and ethers such as tetrahydrofuran, dioxane, and glycol ether. Hydrocarbons such as hexane, kerosene, solvent naphtha, xylene, methylnaphthalene, etc.
Type 2, other halogenated hydrocarbons, acetate esters, etc. Solid diluents or carriers for powders and irrigation agents include mineral powders such as diatomaceous earth, talc, clay, silicate, calcium carbonate, and wood. Examples include plant powders such as flour, wheat flour, and starch, and clathrate compounds such as cyclodextrin.

Examples of emulsifiers, dispersants, and spreading agents include soaps, higher alcohol sulfates, alkylaryl sulfonates, polyoxyethylene alkyl ethers, higher alcohol sulfate salts, polyethylene glycol fatty acid esters, polyhydric alcohol fatty acid esters, and alkyl sulfates. Naphthalene sulfonic acid condensates, polyvinyl alcohol, carboxymethyl cellulose, gum arabic, acrylates, etc. are used.

It can also be mixed with propellants to make aerosols and with combustion agents to make smokes.

Alternatively, it can be processed into paper or non-woven fabric and used in the form of an insect repellent sheet, or it can be kneaded into a synthetic resin sheet, or mixed into latex and used as a backing agent for carpets, etc. to exert a sustained release effect. It can also be used by impregnating fibers or attaching them together with adhesives.

In addition, the range of application can be expanded by appropriately using other indoor malignant mite control agents, repellents, anti-irritants, fragrances, fungicides, fungicides, etc.

The active ingredient used in the tick control agent of the present invention, the compound represented by the general formula If used, 0.
01-10% by weight, 0 in the form of emulsions, irrigation agents, and water solvents
．． A formulation concentration of 1 to 50% by weight is preferred.

The amount of the active ingredient to be applied is preferably 0.1 to 30 g per square meter of area to be treated, and when kneaded into synthetic resin or latex, the content is preferably 0.1 to less than 30% by weight.

[Example] Next, the present invention will be explained in more detail with reference to Synthesis Examples, Examples, and Test Examples, but the present invention is not limited to the following examples unless the gist thereof is exceeded. Note that all "parts" below refer to "parts by weight."

Synthesis Example-1 Production of N-(4-tert-butylbenzyl)-4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxamide 4-chloro-3-ethyl-1-methylpyrazole-5-
1.89 g of carboxylic acid and 20 g of thionyl chloride were heated under reflux for 1 hour. After thionyl chloride was distilled off under reduced pressure, the residue was dissolved in 10 ml of toluene. This is 4-tert
- 1.63 g of butylbenzylamine and 1.21 g of triethylamine in a solution of 0 to 10° in 30 ml of toluene.
It was added dropwise at C. After the dropwise addition, the mixture was stirred for 2 hours, poured into ice water, and extracted with toluene. Add toluene layer to sodium carbonate aqueous solution,
Washed with water and saturated saline. After drying over anhydrous sodium sulfate, it was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain compound (C) 2. listed in Table 1.
97g was obtained. The NMR and IR of this compound were as follows.

'HNMR (CDC13) 5ppm; 1.23
(t, 3H), 1.32 (s, 2.63 (q with 9H)
, 2H), 4.15 (s, 3H).

4.61 (d, 2H), 7.00 (b, LH
).

7.29 (d, 2H), 7.39 (d, 2H
)IR(KBr) cml; 820.1285.15
50.1645.2960.3300 Synthesis Example-2 According to the method of Synthesis Example-1, the compounds listed in Table 1 were obtained.

Table 1 Formulation Example-1 An oil solution was obtained by mixing and dissolving 0.5 parts of compound (a) with 2 parts of xylene and 97.5 parts of kerosene. Also, instead of compound (a), compounds (b), (c), (d), (e
) or (f), respectively, and in the same manner as above, six types of oils were obtained.

Formulation Example 2 10 parts of compound (a), 6 parts of calcium dodecylbenzenesulfonate, 14 parts of polyoxyethylene styrylphenyl ether and 70 parts of xylene were thoroughly mixed to obtain a 10% emulsion. In addition, six types of emulsions were obtained in the same manner except that compounds (b), (C), (d), (e), or (f) were used instead of compound (a).

Formulation Example-3 1 part of compound (a) was thoroughly ground and mixed with 10 parts of white carbon, and further mixed well with 89 parts of clay to obtain a powder. Also, instead of compound (a), compound (b), (
Six types of powders were obtained using each of c), (d), (e), or (f) in the same manner as above.

Formulation Example-4 0.5 parts of compound (a) is mixed and dissolved with 5 parts of xylene and 94.5 parts of odorless kerosene, filled into an aerosol container, and after attaching a valve part, the propellant ( LPG/DME mixed gas) was filled under pressure for 60 minutes to obtain an aerosol. Also, instead of compound (a), compounds (b), (e), (d), (e),
Six types of aerosols were obtained in the same manner as above.

Example-1 Filter paper was cut into 5 x 10 cm, and compound (a), (
b), (C), (d), (e) and (f) were applied uniformly, and after air-drying, 30 southern tick mites were brought into contact with each filter paper, and 2 times were applied to prevent escape.
Fold it in half and secure it with clips on 3 sides, 25°C1 Humidity 75cm
% condition, the mortality rate after 48 hours was examined. As a comparative example, fenitrothion (0,0-dimethyl.-(3-methyl-4-nitrophenyl)phosphorothioate),
Fenthion (o,o-dimethyl 0-(3-methyl-
4-methylthiophenyl)phosphorothioate) and dichlorvos (o-(2,2-dichlorovinyl)0
．． 0-dimethyl phosphate) was similarly treated and tested. The results are shown in Table 2.

Table 2 [Effects of the Invention 1 The pesticidal agent of the present invention exhibits an excellent pesticidal effect against tick mites.

Claims (1)

[Claims] (1) The following general formula [I] ▲Mathematical formulas, chemical formulas, tables, etc. are included▼...[I] (In the above formula, R is a C_1 to C_6 alkyl group, a trifluoromethyl group, or a C_1 to C_3 alkoxy group. 1. A pest control agent for ticks, characterized by containing a pyrazole represented by the following as an active ingredient.