JPH02221245A - Phenoxyphenoxyalkylamine derivative, production thereof and insecticide - Google Patents

Abstract

NEW MATERIAL:A phenoxyphenoxyalkylamine derivative expressed by formula I (R1 is H or lower alkyl; R2 is lower alkyl; n is 2, 3 or 4). EXAMPLE:N-Propyl-3-(4-phenoxyphenoxy) propylamine. USE:An industrially and advantageously producible compound, useful as an insecticide, having excellent juvenile hormone activity and capable of exhibiting ultrahigh controlling effects on insects of the orders Diptera, Lepidoptera, Coleoptera, etc. PREPARATION:For example, as shown in the reaction formula, a compound expressed by formula II (Hal is halogen) is reacted with a compound expressed by formula III in a solvent, such as tetrahydrofuran, in the presence of a base, such as sodium hydroxide, at a temperature, within the range of 0 deg.C to the boiling point of the solvent used to afford the compound expressed by formula I.

Description

[Detailed Description of the Invention] [Field of Industrial Application] The present invention relates to a method for producing a novel phenoxyphenoxyalkylamine derivative having excellent dibenyl hormone activity, and an insecticide containing the compound as an active ingredient. be.

[Conventional technology]

A large number of organic synthetic chemicals are used to control agricultural and sanitary pests, but they have various 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 provides a compound represented by the general formula (wherein R7 represents a hydrogen atom or a lower alkyl group, R represents a lower alkyl group, and n represents 2.3 or 4), a method for producing the same, and the compound @ This is an insecticide characterized by containing liM as an active ingredient.

The compound of the present invention has excellent dibenyl hormone activity and exhibits extremely high control efficacy against insects of the order Diptera, order MUM, order Coleoptera, and the like.

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

(1) Production method a: [■] (I[r) (mV) [■] (In the formula, Hal represents a halogen atom) The reaction is carried out in an organic solvent in the presence of a base, starting at 0°C. It is carried out for 30 minutes to several hours up to the boiling point.

As the organic solvent, any solvent can be used as long as it is inert to the reaction and dissolves the raw materials, such as ethers such as tetrahydrofuran (THE) and dimethoxyethane, and halogenated hydrocarbons such as chloroform.

As the base, sodium hydride, potassium hydroxide, lithium carbonate, triethylamine, pyridine, etc. can be used.

(2) Manufacturing method b: The reaction is carried out in an organic solvent in the presence of a base.

The reaction temperature, reaction time, solvent used, base, etc. are according to manufacturing method a.
It is similar to

Regardless of whether the product is produced using production method a or production method 2, the desired product can be obtained by performing normal post-treatments after the reaction is completed.

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

〔Example〕

Next, the present invention will be explained in more detail with reference to Examples.

Implementation NI N-propyl-3-(4-phenoxyphenoxy)propylamine (compound number 2): 60% NaH0,2 in 20d of THF solution of Furohylamine 111
Add 0g (5,OOe+vol) under ice cooling and foaming power!
'% After completion, 3-(4-phenoxyphenoxypropyl bromide 1.00 g (3,26+wm
10 ml of TIIF solution of ol) was added. After the solution was refluxed for 6 hours, water was added to the reaction mixture and extracted with ether. The ether layer was extracted with 2N HCl, and the aqueous layer was made alkaline with NaOH and extracted with ether. The organic layer is anhydrous.
The oily substance obtained by drying with 5 Oa and distilling off the solvent under reduced pressure was purified by silica gel column chromatography to obtain 0.74 g of the desired product.

Example 2 N-methyl-N-propyl-3-(4-phenoxyphenoxy)propylamine (compound number 6): N-propyl-3-(4-phenoxyphenoxy)propylamine 0.74 g (2,60 m++ mol) 0.50 methyl iodide in 20 ml of dimethoxyethane solution of
g (3,52+*mol) and KzC (h O,4
7 g (3.41 mmol) were mixed and stirred at room temperature for 3 hours. Water was added to the reaction mixture, extracted with ether, washed with water, and dried over anhydrous Mg5O. The residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography to obtain 0.36 g 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.

[! Means for solving IB - Insecticide] The insecticide of the present invention contains the compound represented by the general formula (1) as an active ingredient, and the active ingredient compound can be used as a pure product, but Usually, they are used in the forms that common agricultural chemicals can take, 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 ζ water, etc. are used as the solvent. In these preparations, a surfactant may 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 carriers, surfactants, etc. to be added are not limited to these examples.

[Example 3] Emulsion Compound of the present invention 10 parts Alkylphenylporoxyethylene 5 parts Dimethylformamide 35 parts
Mix and dissolve 50 parts or more of the liquid, dilute with water before use, and spray as an emulsion.

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

[Example 5] Powder 5 parts of the compound of the present invention
Ruri
91 part silica
3 parts Alkylphenylpolyoxyethylene 1 part or more are mixed and pulverized and sprayed 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] Twenty final needle larvae of Culex pipiens were taken in 100 ml of water, and 10 μl of an ethanol solution of each concentration of the sample compound was administered. After rearing for about one week at 2B'C, the inhibition rate of emergence was determined. As a control group, 10μ2 of ethanol was administered, and the corrected emergence inhibition rate 1) was determined using the average value of the eclosion inhibition rate of 17% over the 10 times.

Using the probit 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
ls. was calculated. The results are shown in Table 2.

*) Part 2 table

Claims (4)

[Claims] (1) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_1 is a hydrogen atom or a lower alkyl group, R_1 is a hydrogen atom or a lower alkyl group,
2 represents a lower alkyl group, and n represents 2, 3 or 4. ). (2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, Hal represents a halogen atom, and n represents 2, 3, or 4.) Compounds and general formulas ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1 and R_2 have the same meanings as above.)
A method for producing a compound represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1, R_2 and n have the same meanings as above.) . (3) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1 and n have the same meanings as above.) Compounds represented by the general formula
represents a halogen atom, and R_2 has the same meaning as above. )
A method for producing a compound represented by the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1, R_2 and n have the same meanings as above.) . (4) Contains one or more compounds represented by the general formula ▲ mathematical formula, chemical formula, table, etc. ▼ (in the formula, R_1, R_2 and n have the same meanings as above) as an active ingredient. An insecticide characterized by: