JPS59222479A - Imidazolecarboxyamidine derivative and insecticide - Google Patents

Abstract

NEW MATERIAL:N-( 2,6-Difluorobenzoyl )-N'-( 4-chloro-3-trifluoromethylphenyl )- 1-imidazolecarboxyamidine of formula I . USE:An insecticide having broad insecticidal spectrum, and effective remarkably to various vermin of Lepidoptera, Coleoptera, Diptera order, etc. It has not only larvicidal and ovicidal activities, but also the activity to kill the egg when applied to imagoes. It has low toxicity to warm-blooded animals, and no residual toxicity. PREPARATION:The compound of formula I can be prepared by reacting the thiourea compound of formula II with diimidazole sulfoxide in an organic solvent at 0-50 deg.C, preferably at 0 deg.C- room temperature.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a compound represented by the formula, a method for producing the same, and an insecticide containing the compound as an active ingredient.

The compound of the present invention has a wide insecticidal spectrum and has excellent efficacy against various insect pests such as Lepidoptera, Coleoptera, and Diptera, and has not only larvicidal and ovicidal effects, but also when treated with adult insects. It also has the effect of killing the eggs that are being laid. It has been widely known that benzoylurea derivatives represented by the following general formula have insecticidal activity. (
% Kaimei No. 46-6550, No. 51-101950, 52
-10239, etc.) However, the compounds of the present invention not only have superior insecticidal efficacy compared to the known compounds;
In particular, it has a strong ovicidal effect.

There is a strong need for a control agent with ovicidal action against pests such as the globally important silver leaf moth and leafminer moth, which immediately infiltrate fruits and leaves and cause damage. The compound of the present invention is an insecticide with a wide range of applications. In addition, it is an excellent insecticide with low toxicity to warm-blooded animals and no concerns about residual toxicity. In producing the compound of the present invention, N-(2,6-difluoropenzoyl)-N'-(4-chloro-3-trifluoromethylphenyl)thiourea and diimidazole sulfoxide are reacted in an organic solvent. . Diimidazole sulfoxide is produced by reacting imidazole and thionyl chloride in an organic solvent, and is usually reacted with thiourea represented by the above formula (1) without isolation. As the organic solvent, common inert solvents such as methylene chloride, chloroform, and acetonitrile can be used. The reaction temperature is 0 to 50°C, preferably θ°C to room temperature, for 5 to 10 hours.

The structure was determined from spectral analysis such as IR, MASS, and NMR.

The compound of the present invention has two types of tautomeric structures shown below, each of which further includes cis and trans isomers. The present invention also includes b-shifted isomers.

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

Example I N-(2,6-chloroolbenzoyl)-N'-(4-
Synthesis of chloro-3-trifluoromethylphenyl)-1-imidazolecarboxamidine
f was dissolved in dry methylene chloride 201d, and 1.
Add 5f of thionyl chloride dropwise. Under water cooling KN-(2,6
-chloroolbenzoyl)-N'-(4-chloro-3-
4.5 f of trifluoromethylphenyl)thiourea were added and the reaction solution was stirred at room temperature for 7 hours. After the reaction was completed, the insoluble materials were separated and the F liquid methylene chloride was washed with water. The precipitated white crystals were separated from each other, washed with ether, and dried to obtain the desired product N-(2,6-chloroolbenzoyl).
-N'-(4-chloro-3-trifluoromethylphenyl)-1-imidazolecarboxyamidine 3.4t om, p, 149 150°C The insecticide of the present invention is a compound represented by formula (1) Although it can be used as a pure product of the active ingredient compound, it is usually used in a form that can be used with general agricultural chemicals, that is, as an irrigation agent,
It is used in the form of powder, emulsion, flowable, etc. As additives and carriers, vegetable powders such as soybean flour and wheat flour, and mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, pyrophyllite, and clay are used for solidifying agents. .

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 preparations, a surfactant can be added if necessary in order to obtain a uniform and uniform form. Irrigation agents, emulsions, flowables, etc. obtained in this way are diluted with water to a predetermined concentration and used as suspensions or emulsions, and powders and granules are used as they are by spraying them on plants. .

Next, examples of formulations will be shown, but the carriers, surfactants, etc. to be added are not limited to these examples.

Example 2 Emulsion Compound of the present invention 10 parts Alkylphenylpolyoxyethylene 5I dimethylformamide 35' xylene 50 The above ingredients are mixed and dissolved, and before use, the mixture is diluted with water and sprayed as an emulsion.

Example 3 Wettable powder Compound of the present invention 20 parts Higher alcohol sulfate 5r
A 7
Part 4 white carbon
11 or more are mixed and pulverized into a fine powder, and before use, it is diluted with water and sprayed as a suspension.

Example 4 Powder Compound of the present invention 9 parts Tal
ri 91
l silicone
3N alkyl phenyl polyoxyethylene 11 or more are mixed and pulverized and sprayed as is when used.

It goes without saying that the compound of the present invention is sufficiently effective alone, but since it is slow-acting against larvae, it is extremely useful when used in combination with one or more fast-acting insecticides. . In addition to fast-acting insecticides, the compound of the present invention can also be used in combination with one or more fungicides and acaricides.

Representative examples of insecticides that can be used in combination with the compounds of the present invention are shown below.

Organophosphorus insecticide, carbamate insecticide fenthion,
Fenitrothion, diazinon, chlorpyrifos, E
SP1 pamidothione, phenthoate, dimethoate,
Formothion, Marathon, Dibuterex, Thiometone, Dichlorvos, Acephate, Cyanophos, Pirimiphos Methyl, Inxathion, Pyridafenthione, Chlorpyrifos, DMrP, Prothiofos, CVMP, Salithion, EPN, CYP1 Aldicarb, Propoxynil, Virimicarb, Methomyl, Cartap, Carbaryl, Nicotine Pyrethroid insecticides vermethrin, cypermethrin, decamerin, fenparerate, 7-enpropathrin, cyhalothrin,
fluparinate, phencyfre), trary) surin, cyfluthrin, fluparinate, pyrethrin, allethrin, tetramethrin, resmethrin, parsulin,
Cymethrin, Propathrin, Flosulin Next, test examples will be given to demonstrate the insecticidal activity of the compounds of the present invention.

Experimental Example 1 Efficacy against diamondback moth The compound of the present invention was prepared according to the emulsion formulation shown in Example 2.
The compound concentration was diluted with water to be 313.7.8 ppm K''. Cabbage leaves were immersed in the chemical solution for 30 seconds, and after air-drying, the leaves were placed in a 93-diameter petri dish containing five 3rd instar diamondback moth larvae. The petri dish was placed in a constant temperature room at a temperature of 25°C and a humidity of 65% for 12 repetitions.
The insect killing rate after 0 hours was determined. The result is as follows.

*Known compound A: N-(2,6-difluoropenzoyl)-N'-(4-chloro-3-trifluoromethylphenylene/I/) urea (JP-A-52-10239 Experimental Example 2 Efficacy against Spodoptera japonica) The invention compound was prepared according to the emulsion formulation shown in Example 2, and the compound concentration was 3.
It was diluted with water to a concentration of 1.3.7.8 ppm. Soak sweet potato leaves in the chemical solution for 30 seconds, air dry, then)
The leaves were placed in a 9071-diameter Petri dish containing five 3rd instar Spodoptera larvae and covered with a glass lid. With 2 repetitions,
Place the petri dish in a constant temperature room with a temperature of 25°C and a humidity of 65°C.
The insect killing rate was determined after 120 hours. The result is as follows.

The control compound was the same as in Experimental Example 1.

Experimental Example 3 Effect against fall armyworm The compound of the present invention was prepared according to the emulsion formulation shown in Example 2.
It was diluted with water so that the compound concentration was 125.31.3 ppm. Corn leaves were immersed in the chemical solution for 30 seconds, and after air drying, the leaves were placed in a 9cm diameter Petri dish containing five 3rd instar fall armyworm larvae and covered with a glass lid.

In two repetitions, the petri dish was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 65° C., and the insect killing rate after 120 hours was determined. The result is as follows.

The control compound was the same as in Experimental Example 1.

Experimental Example 4 Efficacy against diamondback moth eggs The compound of the present invention was prepared according to the emulsion formulation shown in Example 2.
It was diluted with water so that the compound concentration was 125.31.3 ppm. Diamondback moth eggs were immersed in the chemical solution for 30 seconds, air-dried, and then placed in a petri dish. Close the glass lid and heat to 25°C.
The eggs were placed in a constant temperature room with a humidity of 65 degrees, and the egg killing rate was examined after 7 days. The result is as follows.

The control compound was the same as in Experimental Example 1.

Experimental Example 5 Effect on armyworm eggs The compound of the present invention was prepared according to the emulsion formulation shown in Example 2.
It was diluted with water so that the compound concentration was 500.125 ppm. Soak armyworm eggs in the chemical solution for 30 seconds,
After air drying, it was placed in a petri dish. Close the glass lid and set the temperature to 25.
The eggs were placed in a constant temperature room at 65% humidity and the egg killing rate was examined after 7 days. The result is as follows.

The control compound was the same as in Experimental Example 1.

Applicant: Japan Blind Co., Ltd. Agent: Haruyuki Ito Same as: Yoshimi Yokoyama

Claims (1)

[Claims] A compound represented by: 1. A method for producing a compound represented by the formula, which comprises reacting the compound represented by the formula with diimidazole sulfoxide. An insecticide characterized by containing a compound represented by as an active ingredient.