JPH0655649B2 - Method for preventing decomposition of sulfenylcarbamate derivative - Google Patents

Description

TECHNICAL FIELD The present invention relates to a method for preventing decomposition of a sulfenylcarbamate derivative.

Conventional technology General formula [Wherein R ₁ and R ₂ are the same or different and each represents a C _{1 to} C ₈ alkyl group, a C _{3 to} C ₆ cycloalkyl group, a phenyl group, a benzyl group, a -X-COOR ₃ group or a -Y-CN group. . Here, X and Y are each a C ₁ -C ₆ alkylene group, R ₃
Represents a C ₁ -C ₈ alkyl group or a C ₃ -C ₆ cycloalkyl group. Ar is Or Indicates. ] A sulfenyl carbamate derivative represented by is a pest, a tick, a nematode, etc. belonging to hemiptera, Lepidoptera, Coleoptera, Diptera, Thysanoptera, orthoptera It is characterized by having an excellent insecticidal activity and controlling effect against sanitary pests and having extremely weak toxicity to warm-blooded animals. Regarding the sulfenylcarbamate derivative,
For example, JP-A-50-48137 and JP-A-57-2
It is described in detail in Japanese Patent Laid-Open No. 00377, Japanese Patent Laid-Open No. 58-92655, and the like.

The sulfenylcarbamate derivative represented by the general formula [I] has excellent properties as described above,
On the other hand, it may change over time,
Insufficient in terms of long-term storability and high-temperature storability.
In particular, when the sulfenylcarbamate derivative is formulated using a mineral carrier, the active ingredient, the sulfenylcarbamate derivative, often decomposes violently.

Means for Solving the Problems In view of the present situation, the present inventor has conducted diligent research to improve the stability of the sulfenylcarbamate derivative represented by the general formula [I], and as a result, the sulfenyl It has been found that the addition of amines to the carbamate derivative can prevent the derivative from decomposing and achieve the object of the present invention. The present invention has been completed based on such findings.

That is, the present invention relates to a method for preventing decomposition of a sulfenylcarbamate derivative, which comprises adding a tertiary amine to the sulfenylcarbamate derivative represented by the above general formula [I].

As the sulfenylcarbamate derivative of the general formula (I) to be incorporated in the insecticide composition of the present invention, any conventionally known one can be used as long as it is included in the above general formula, and specifically, Compounds of

2,3-dihydro-2,2-dimethyl-7-benzofuranyl N- [N- (2-ethoxycarbonylethyl)
-N-isopropylaminosulfenyl] -N-methylcarbamate (hereinafter referred to as "compound 1") 2,3-dihydro-2,2-dimethyl-7-benzofuranyl N- (N, N-dibutylaminosulfenyl)
-N-methylcarbamate (hereinafter referred to as "compound 2") S-methyl-N-{[N-methyl-N- (N-benzyl-N-ethoxycarbonylethylaminosulfenyl) carbamoyl] oxy} thioacetimidate (Hereinafter referred to as "Compound 3") S-methyl-N-{[N-methyl-N- (N-isobutyl-N-ethoxycarbonylethylaminosulfenyl) carbamoyl] oxy} thioacetimidate (hereinafter referred to as "Compound 4" As the tertiary amine used in the present invention, conventionally known ones can be widely used, and examples thereof include triethylamine, tributylamine, C ₄ -C ₁₆ alkyldimethylamine (specifically butyldimethylamine, hexyldimethyl). Amine, octyldimethylamine, decyldimethylamine,
Lauryldimethylamine, stearyldimethylamine, etc.), C ₄ -C ₁₆ alkyldiethylamine (specifically, butyldiethylamine, hexyldiethylamine, octyldiethylamine, decyldiethylamine, lauryldiethylamine, stearyldiethylamine, etc.), N, N-dimethylaniline, N,
Examples thereof include aromatic amines such as N-diethylaniline, triethanolamine, polyoxyethylene alkylamines and the like. Among these, polyoxyethylene alkylamines are particularly preferable. More specifically, examples of polyoxyethylene alkylamines include Amate 102, Amate 105, Amate 110, Amate 301, Amate 302, Amate 304, Amate 307, Amate 308, Amit 320, Amate 4
15 (all trade names, manufactured by Kao Corporation) and the like. The compounding amount of the above amines is a composition in which the kind of amines used, the sulfenylcarbamate derivative of the above general formula [I] of the present invention and a tertiary amine are blended (hereinafter referred to as “the composition of the present invention”). Although it cannot be generally stated that it varies depending on the formulation form of the "product"), it is usually about 0.01 to 20% by weight based on the above sulfenylcarbamate derivative,
It is preferably about 0.05 to 10% by weight.

The composition of the present invention may further contain an epoxy compound and / or polyoxyethylenes. Examples of the epoxy compound include glycidol, butyl glycidyl ether, hexyl glycidyl ether, octyl glycidyl ether, decyl glycidyl ether, lauryl glycidyl ether, phenyl glycidyl ether, and epoxidized vegetable oil. Examples include polyoxyethylene lauryl ether, polyoxyethylene octyl ether, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitate tetraoleate, and polyoxyethylene sorbitan monostearate. By blending such an epoxy compound and polyoxyethylenes, the stability of the sulfenylcarbamate derivative can be further improved. The amount of the epoxy compound and / or polyoxyethylene compounded is usually about 0.01 to 2% by weight with respect to the sulfenylcarbamate derivative.

The composition of the present invention can take various dosage forms such as granules, fine granules, wettable powders and powders. In preparing such a pharmaceutical form, a known carrier or the like usually used in this field can be used. As such a carrier, for example, a mineral carrier such as bentonite, diatomaceous earth, or white carbon, or a powdery substance thereof as a binder, a surfactant (for example, alkylbenzene sulfonate, sodium lignin sulfonate, etc.), water or the like is used. Examples thereof include granulated products.

EFFECTS OF THE INVENTION According to the present invention, it is possible to prevent decomposition of the sulfenylcarbamate derivative by adding amines to the sulfenylcarbamate derivative represented by the general formula [I], and thus the composition of the present invention is It is extremely excellent in terms of long-term storability and high-temperature storability. In particular, even when the sulfenylcarbamate derivative is formulated using a mineral carrier, the sulfenylcarbamate derivative as an active ingredient is less likely to be decomposed.

Examples The present invention will be further clarified with reference to Examples and Test Examples below. In the following, simply "part" means "part by weight"
"%" Means "% by weight".

Example 1 Compound Part 1 5 Amate 102 4 Granular Carrier (Natural Small Pumice Stone) 91 By mixing Compound 1, Amate 102 and Granular Carrier using a mixer and adsorbing Compound 1 and Amate 102 on the Granular Carrier The target 5% granule was obtained.

Example 2 A 5% granule was obtained in the same manner as in Example 1 except that 4 parts of Amate 105 was used instead of 4 parts of Amate 102.

Example 3 5% granules were prepared in the same manner as in Example 1 except that 1 part of amite 102 and 1 part of epoxidized soybean oil [trade name Newcalgen 800, manufactured by Takemoto Yushi Co., Ltd.] were used instead of 4 parts of Amate 102. Got

Example 4 Amate 102 5% granules were obtained in the same manner as in Example 1 except that 1 part of amite 102 and 1 part of polyoxyethylene [trade name: Solpol 7157, manufactured by Toho Kagaku] were used instead of 4 parts of amite 102. It was

Example 5 A 5% granule was obtained in the same manner as in Example 1 except that 5 parts of compound 2 was used instead of compound 1.

Example 6 5% granules in the same manner as in Example 5 except that 1 part of the amate 102 and 1 part of the epoxidized soybean oil [trade name Newcalgen 800, manufactured by Takemoto Yushi Co., Ltd.] were used instead of the 4 parts of the amate 102. Got

After mixing thoroughly Example 7 Blend unit Compound 1 40 AMIET 102 2 White carbon 20 diatomaceous earth 34 alkylbenzenesulfonates 2 lignosulfonate sodium 2 above various components using a mixer, and pulverized using a fine grinding mill The target 40% wettable powder was obtained.

Example 8 A 40% wettable powder was obtained in the same manner as in Example 7 except that 2 parts of Amate 105 was used instead of 2 parts of Amate 102.

Example 9 40% hydration in the same manner as in Example 7 except that 1 part of the amate 102 and 1 part of the epoxidized soybean oil [trade name Newcalgen 800, manufactured by Takemoto Yushi Co., Ltd.] were used instead of the 2 parts of the amate 102. I got an agent.

Example 10 A 40% wettable powder was obtained in the same manner as in Example 7 except that 40 parts of compound 2 was used instead of compound 1.

Test Example 1 The granules or wettable powders obtained in Examples 1 to 10 were treated at 60 ° C. for 1 hour.
After standing for 6 months or at room temperature (20 ° C.) for 6 months, the decomposition rate of the active ingredient compounds (Compound 1 and Compound 2) was measured. High performance liquid chromatography was used for the measurement. The results are shown in Table 1.

Test Example 2 Compound 1 was mixed with 2% or 4% of various amines shown in Table 2 below.
% Was added at 60 ° C. for 1 month or at room temperature (20 ° C.) for 6 months, and the decomposition rate of Compound 1 was measured. High performance liquid chromatography was used for the measurement. The results are shown in Table 2.

Test Example 3 Compound 1, compound 2, compound 3 and compound 4 to which 4% of Amate 102 was added respectively were allowed to stand at 60 ° C. for 1 month or at room temperature (20 ° C.) for 6 months to obtain the active ingredient compound (compound 1, compound 1 The decomposition rates of 2, compound 3 and compound 4) were measured. High performance liquid chromatography was used for the measurement. The results are shown in Table 3.

Claims (2)

[Claims] 1. A general formula [Wherein R ₁ and R ₂ are the same or different and each represents a C _{1 to} C ₈ alkyl group, a C _{3 to} C ₆ cycloalkyl group, a phenyl group, a benzyl group, a -X-COOR ₃ group or a -Y-CN group. . Here, X and Y are each a C ₁ -C ₆ alkylene group, R ₃
Represents a C ₁ -C ₈ alkyl group or a C ₃ -C ₆ cycloalkyl group. Ar is Indicates. ] A method for preventing decomposition of a sulfenylcarbamate derivative, which comprises adding a tertiary amine to the sulfenylcarbamate derivative represented by: 2. The method for preventing decomposition according to claim 1, wherein the tertiary amines are polyoxyethylene alkylamines.