JPH02221248A - Hydroxyamine derivative, derivative thereof and insecticide - Google Patents

Abstract

NEW MATERIAL:A hydroxyamine derivative expressed by formula I (R1 and R2 are H or lower alkyl; X is lower alkyl; n is 0, 1 or 2; m is 2 or 3). EXAMPLE:O-[2-(4-Phenoxyphenoxy) ethyl]-N-propylhydroxyamine. USE:An industrially and advantageously producible compound, useful as an insecticide, having excellent juvenile hormone activity (juvenile hormone related to metamorphotic phenomenon unique to insects) and capable of exhibiting ultrahigh controlling effects on insects of the orders Diptera, Lepidoptera, Coleoptera, etc. PREPARATION:A compound expressed by formula II is reduced with a reducing agent, preferably sodium cyanoboron hydride, in a solvent, such as alcohol, at 0-50 deg.C under acidic conditions to afford the compound expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for producing a novel hydroxyamine derivative having excellent dibenyl hormone activity, and an insecticide containing the compound as an active ingredient.

[Conventional technology]

A large number of organic synthetic chemicals are used to control agricultural and sanitary pests, but they have many problems such as residual toxicity, environmental pollution, and the emergence of resistant pests. Therefore, in recent years, pesticide development has been progressing with a focus on substances produced by living organisms.

[Problem to be solved by the invention]

The purpose of the present invention is to focus on juvenile hormone (dibenyl hormone) related to the metamorphosis phenomenon peculiar to insects, and to show excellent efficacy.
Moreover, the objective is to find a compound that can be produced industrially advantageously.

[Means to solve the problem]

The present invention relates to a compound represented by the general formula (wherein R+ and R2 each represent a hydrogen atom or a lower alkyl group, X represents a lower alkyl group, n represents Oll or 2, and m represents 2 or 3), The present invention is an insecticide characterized by its production method and by containing the compound as an active ingredient.

The compound of the present invention has excellent dibenyl hormone activity and exhibits extremely high control efficacy against insects such as Diptera, Lepidoptera, and Coleoptera.

The compound of the present invention can be produced according to the following reaction formula.

The reaction proceeds with a normal reducing agent, but if the reducing agent is too strong, the target product produced may be further reduced.
It is preferable to use sodium cyanoborohydride (NaBHsCN) or the like.

When using NaBflICN, the reaction is carried out in a solvent such as alcohol under acidic conditions at 0°C to 50°C for 30 minutes to several hours.

After the reaction is completed, the desired product can be obtained by performing usual post-treatments.

The structure of the compound of the present invention was determined by IR, NMR single elemental analysis, etc.

The compound of the present invention represented by general formula (f) can also be produced according to the following reaction formula.

(In the formula, Hal represents a halogen atom.) [Example] Next, the present invention will be explained in more detail with reference to Examples.

Example 1 0-(2-(4-phenoxyphenoxy)ethyl]-N-propylhydroxyamine (compound no. 1
) The reaction solution, which was stirred at room temperature for 2 hours while being added dropwise, was diluted with 2NNa.
The mixture was neutralized with CO3, water was added, and the mixture was extracted with ether.

After washing the extract with water and drying over anhydrous Mg5Oa, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 0.81 g (yield: 81%) of the target product in the form of an oil.

Table 1 shows representative examples of the compounds of the present invention produced in the same manner as in the above examples.

0.22 g of O-(2-(4-phenoxyphenoxy)ethyl)propionaldoxime in 5-methanol (
0.77 mmof) and a small amount of methyl red as an indicator were dissolved, and 1.2 drops of a methanol solution of hydrogen chloride was added to change the indicator to red. Add NaBHsC to this solution.
Add 0.88 g (1,17 m++*ol) of N;
[Means for solving the problem - Insecticide] The insecticide of the present invention contains a compound represented by the general formula (1) as an active ingredient. Although the pure active ingredient compound can be used as is, it is usually used in the form of general agricultural chemicals, such as wettable powders, powders, emulsions, and flowables.

As additives and carriers, if the purpose is to use solid agents,
Vegetable powders such as soybean flour and wheat flour, and fine mineral powders such as diatomaceous earth, apatite, gypsum, talc, pyrophyllite, and clay are used.

For liquid formulations, use kerosene, mineral oil, petroleum,
Solvent naphtha, xylene, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, water, etc. are used as the solvent. In these formulations, surfactants can be added if necessary to obtain a uniform and stable form. The wettable powders, emulsions, flowables, etc. obtained in this way can be diluted with water to a predetermined concentration to form a suspension or emulsion, and the powders and granules can be used as they are by spraying them on plants. Ru.

[Example - Insecticide] Next, examples of formulations will be shown, but the carrier, surfactant, etc. to be added are not limited to these examples.

(Example 2) Emulsion Compound of the present invention 10 parts Alkylphenylpolyoxyethylene 5 parts Dimethylformamide 35 parts
N 50
Mix and dissolve 1 part or more, dilute with water before use, and spray as an emulsion.

[Example 3] Permanent agent: 20 parts of the compound of the present invention, 5 parts of higher alcohol sulfate ester
A 7
4 parts white carbon 1 part or more are mixed together, ground into a fine powder, diluted with water before use, and sprayed as a M suspension.

[Example 4] Powder 5 parts of the compound of the present invention
Ruri
91 parts*) Alkylphenylpolyoxyethylene 1 part or more is mixed and pulverized and sprinkled as is when used.

〔Effect of the invention〕

Next, test examples will be given to demonstrate the insecticidal activity of the compounds of the present invention.

[Test Example 1] 20 final instar larvae of Culex mosquito were added to 10 ml of water.
10 μi of an ethanol solution of each concentration of sample compound was administered. After rearing at 28°C for about one week, the inhibition rate of emergence was determined. As a control group, 10 al of ethanol was administered, and the corrected eclosion inhibition rate was determined using the average value of the eclosion inhibition rate of 7% over the 10 times.

Using the problt conversion method from the corrected eclosion inhibition rate of each concentration, the inverse logarithm of the half eclosion inhibition concentration of the sample compound, p
lso was calculated. The results are shown in Table 2.

No. table Applicant (430) Nippon Soda Co., Ltd.

Claims (3)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_1 and R_2 each represent a hydrogen atom or a lower alkyl group, 2 or 3). (2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X, R_1, R_2, n and m have the same meanings as above.) A method for producing a compound represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (X, R_1, R_2, n and m have the same meanings as above). (3) One or more compounds represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (X, R_1, R_2, n and m have the same meanings as above) as an active ingredient. An insecticide characterized by containing.