JPS6081109A - Insecticide composition - Google Patents

Abstract

PURPOSE:An insecticide composition stable for a long period even under high temperature, containing a sulfenylcarbamate derivative, and epoxy compound obtained from a (poly)ethylene glycol derivative and epichlorohydrin. CONSTITUTION:An insecticide composition containing a compound shown by the formula I [Ar is group shown by the formula II or formula III; R<1> and R<2> are -X-COOR<3>, -Y-CN (X and Y are 1-6C alkylene; R<3> is 1-8C alkyl, or 3-6C cycloalkyl), further R<2> may be 1-8C alkyl, benzyl, etc.] and a compound shown by the formula IV (R5 is H, or 1-3C alkyl; n is 1-20 integer). 0.01-40wt% compound shown by the formula II is added to the compound shown by the formula I , and this addition prevents decomposition of the compound shown by the formula I , and gives a composition having improved high-temperature shelf stability for a long period.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an insecticide composition, and an object thereof is to provide an insecticide composition with excellent stability.

The general formula is shown. R1 and R2 are the same or different groups -X-CO
represents OR3 or the group -Y-CN. Here, X and Y each represent an alkylene group of 01-6, and R3 represents a C1-8 alkyl group or a C3-6 cycloalkyl group. −
Furthermore, R2 is a C1-8 alkyl group, a 03-6 cycloalkyl group, a benzyl group that may have a substituent,
Phenyl group or group -Z-R4 which may have a substituent
may also be shown. Here, 2 represents a carbonyl group or a sulfonyl group, and R4 is a C1-6 alkyl group, a C1-6 alkoxy group, a phenoxy group, a benzyl group that may have a substituent, or a phenyl group that may have a substituent. shows. Each of the above substituents is a halogen atom, a 01-3 alkyl group, or a C1-3 alkoxy group. The sulfenyl carbamate derivatives represented by ] are pests belonging to the orders Hemiptera, Lepidoptera, Coleoptera, Diptera, Threadoptera, Orthoptera, etc.
It has excellent insecticidal activity or control effect against agricultural, forestry, and sanitary pests such as mites and nematodes, and is characterized by extremely low toxicity to warm-blooded animals, and contains said derivatives. The present inventor has already filed a patent application for the insecticide composition [Belgium Special Patent No. 890162]
and Belgian patent 892802].

However, in the course of subsequent research, it was found that the above derivatives sometimes undergo changes over time and are particularly unsatisfactory in terms of long-term storage and high-temperature storage.

The present inventors have made extensive studies on suppressing the decomposition of the sulfenyl carbamate derivatives represented by the general formula [I].
It has been found that the decomposition of the sulfenyl carbamate derivative represented by [I] can be prevented and the purpose of stabilization can be achieved. The present invention has been completed based on such knowledge.

The insecticide composition of the present invention is stable over a long period of time and also has excellent stability at high temperatures.

The sulfenyl carbame) f4 conductor represented by the above general formula [I] used in the present invention is a known compound, and can be easily obtained, for example, by the following formula.

[In the formula, Ar, R1 and R2 are the same as above] The epoxy compound used in the present invention is a compound represented by the following general formulas.

5 [In the formula, R5 represents a hydrogen atom or a C1-3 alkyl group. n represents an integer from 1 to 20. ] The compound with the general formula [Tan] is a known compound and is easily produced by reacting an ethylene glycol derivative or a polyethylene glycol derivative with epichloro μhydrin, and the number of n can be arbitrarily selected, but in the present invention, When n is 20 or more, the compatibility deteriorates, and it is necessary that the number is less than that. The amount of the epoxy compound added is based on the formula [IJ
Generally, the amount can be within the range of 0.01 to 40% by weight based on the sulfenyl carbamate derivative represented by, and may be arbitrarily selected depending on the 8A class of the epoxy compound and the type of dosage form. For example, in order to stabilize the compound of formula [I], the oxirane oxygen of the epoxy compound (the ratio of oxirane oxygen to the molecular claw of the epoxy compound) is 20 to 25%.
For compounds with oxirane oxygen content of 10=20%, the amount added is 0.01 to 2%.
If the compound contains 0 weight percent and oxirane oxygen content of 5 to 10%, the addition amount can be 5 to 20% by weight. In the case of granules, the ratio of the epoxy compound to the compound of formula (I) is 10 to 4
It is better to add 0% of nails. In the case of hydrating agents, the formula [1
It is preferable to add 0.1 to 10% by weight of the epoxy compound to the compound. In the case of an emulsion, the epoxy compound is added in an amount of 0.1-10fiffi to the compound of formula (I).
It is better to add %.

By the above method, the sulfenyl carbamate derivative represented by the general formula [IJ] has a decomposition rate of 3 when stored at 60°C for 1 month.
% or less, almost no decomposition will be observed after storage at room temperature (20°C) for 6 months.

In order to explain the present invention in more detail, Examples and Test Examples are shown below.

Example 1 (5% granules) M % N-Methyl carbamate granular carrier (small natural pumice) 9B, 0 Li U The test compound and stabilizer were mixed together with an oil-absorbing granular carrier using a mixer. Then, the desired granules are obtained by adsorbing the test compound and the stabilizer onto the granular carrier.

Example 2 (40% hydrating agent) Heavy % Nyl]N-methylcarnomate white carbon 20.0 Diatomite 88.5 Alkylbenzenesulfone fi salt 2.0 Sodium ligninsulfonate 2.0 or more compounds in a mixer Mix thoroughly with a pulverizer, and then pulverize with a pulverizer to obtain the desired wettable powder.

Example 3 (80% emulsion) M % Cetimidate Tween B g 6.5 Span 80 8.5 Xylene 59 The above compounds were thoroughly mixed and dissolved using a mixer to obtain the desired emulsion.

Test Example 1 2.8-dihydro-2,2-dimethyl-7-benzofuranyl N-[N-(2-ethoxycarbonylethyl)-
N-isopropylaminosulfenyl compound was added at 4% by weight, and the decomposition rate was measured after 1 month at 60°C and 6 months at room temperature (20°C). Table 11
I showed this.

Test Example 2 To each of our sulfenyl carbamate derivatives was added 1 at 6% °C.
The decomposition rate was measured after 6 months at room temperature (20°C) and is shown in Table H.

Table ■ Test Example 8 The decomposition rates of the granules, wettable powders, and emulsions prepared in Example 1, Example 2, and Example 8 were measured after storage at 60°C for 1 month and at room temperature for 6 months. It was shown to.

Table ■ Trial Example 4 A diluted solution of an 80% emulsion at a predetermined concentration prepared according to Example 8 was sprayed on rice plants (1 month old seedlings) planted in pots until the leaves were sufficiently covered. After air-drying, cover the leafhopper (Nephotettix cincticeps)
Ten adult insects were provided. The test was conducted in duplicate, and the mortality rate is shown in Table ①. For comparison, a plot without the addition of stabilizers was created.

Table ■ (Note) Sulfenyl carbamate derivative A: 2,8-dihydro-2,2-dimethyl-7-benzofuranyl N-[N-(2-ethoxycarbonylethyl) -N-inpropylaminosulfenyl IN-methylcarbamate B: 2,8-dihydro-2,2-dimethyl-7-benzofuranyl N-[N-(2-ethoxycarbonylethyl)-N-butylaminosulfenyl 3N-methylcarbamate C: 2,8-dihydro-2, 2-dimethyl-7-benzofuranyl N-[N-(2-ethoxycarbonylethyl)-N-benzyl rminosulfenyl]
N-methyl carbamate D: S-methyl-N-[(N-
Methyl-N-(N-isopropyl-ethoxycarbonylethylaminosulfenyl)carbamoyl)oxycothioacetimidate ESS-Methyl-N-[(N
-Methyl-N-(N-benzyl-N-ethoxycarbonylethylaminosulfenyl ÷ soil S-1-1S-2 LF: S-methyl-N-[(N-methyl-N-(N -Inbutyl-N
- Ethoxycarbonylethylaminosulfenylcarbamoyl)oxycothioacetimidate Presence or absence of stabilizer m: As shown in the results above no addition, the addition of the stabilizer had no adverse effect on biological effects. Also, no drug damage was observed.

Furthermore, similar results were obtained when a hydrating powder manufactured by a method similar to Example 2 was used.

(that's all) Agent: Patent Attorney Eiji Sanae

Claims (1)

[Claims] ■ General formula () is shown. R1 and R2 are the same or different groups -X-CO
represents OR3 or the group -Y-CN. Here, X and Y each represent an alkylene group of 01-6, and R3 represents an alkyl group of 01-8 or a cycloalkyl group of C3-6. Furthermore, R2 may represent a C1-8 alkyl group, a C3-6 cycloalkyl group, a benzyl group that may have a substituent, a phenyl group that may have a substituent, or a group -Z-R4. Here, 2 represents a carbonyl group or a sulfonyl group, and R4 is a 01-6 thylkyl group, a C1-6 alkoxy group, a phenoxy group, a benzyl group that may have a substituent, or a phenyl group that may have a substituent. shows. Each of the above substituents is a halogen atom, a C1-3 alkyl group, or a C1-3 alkoxy group. ] In the sulfenyl carbamate derivative and the general formula E, R5 represents a hydrogen atom or an alkyl group of 01 to 3. n represents an integer from 1 to 20. ] An insecticide composition characterized by containing a compound represented by the following.