JPS6391367A - Benzoylurea compound and insecticidal and miticidal composition containing said compound as active component - Google Patents

Abstract

NEW MATERIAL:A benzoylurea compound of formula I [R is halogen; R1 is halogen or H; R2 is group of formula II (R3 and R4 are alkyl, cycloalkyl or aryl)]. EXAMPLE:Methyl [4-[2-[3-chloro-5-( trifluoromethyl )]pyridyloxy ]-phenyl-7-(2,6- difluorophenyl)-2-methyl-5,7-dioxo-3-thia-2,4,6-triazaheptan oate. USE:An insecticidal and miticidal agent. It has not only strong insecticidal activity against various vermin but also extremely high effect against parasitic mites of animal and vegetable. It exhibits larvicidal action by the activity to inhibit ecdysis of larva, ovicidal action and sterilizing action to imago to lay unhatchable egg. PREPARATION:The compound of formula I can be produced by reacting the compound of formula III with the compound of formula IV in an inert solvent at a temperature between -10 deg.C and the boiling point of the reaction mixture.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a novel benzoyl urea compound, an insecticide or acaricide composition containing the compound as an active ingredient, and a method for controlling pests and mites using the compound. Regarding how to.

PRIOR ART Various derivatives of N-benzoyl-N'-arylureas having insecticidal activity are already known, among which the currently commercially available one is generalized diflubenzuron, namely 1-(4-chlorophenyl)- 3-(2,6-
Difluoro)benzoyl urea (Japanese Unexamined Patent Publication No. 46-6550) is a typical example. However, although this compound has insecticidal power, it is only effective against a very limited number of mites. A patent application publication that describes insecticidal and acaricidal activity is JP-A-59-1762.
No. 45, JP-A-60-231635 and JP-A-61
-63649 etc.

Problems to be solved by the invention
No. 1635 and Japanese Unexamined Patent Publication No. 61-63649, etc., describe acylurea compounds that have insecticidal and acaricidal effects, but for reasons of environmental pollution or economical reasons, even lower-drug compounds have been developed. The emergence of a compound that is effective in small amounts has been strongly desired.

Means for Solving the Problems As a result of various studies on novel acylurea compounds, the present inventors found that the general formula [I] (wherein R represents a halogen atom, R represents a halogen atom or a hydrogen atom, and R2 represents -N-C○OR4, and R3 and R4 each represent an alkyl group, a cycloalkyl group, or an aryl group) exhibits extremely strong insecticidal and acaricidal activity, and also causes phytotoxicity to plants, human and livestock There is almost no toxicity to
The present invention was completed after discovering that it can be used as an extremely practical insecticide and acaricide.

The compound of the present invention represented by the above general formula CI, 1 can be produced by reacting the compound represented by the general formula (II"1 ρ with 1) and the compound represented by the general formula [■] (In these formulas, R, R+ and R2 are as defined in the general formula [Equation]). It is carried out at 10° C. to the boiling temperature of the reaction mixture.

In addition, the compound represented by the above general formula CIII) is
4-(2-(3-chloro-5-(trifluoromethyl))pyridyloxy]aniline represented by the formula CrV) and a sulfenyl halide represented by the general formula [■] (wherein R2 is as defined in general formula CI, and X represents a gen atom)
. This reaction is carried out in an inert solvent such as a hydrocarbon or chlorinated hydrocarbon in the presence of a base such as triethylamine at -20°C to room temperature.

The acylurea compound of the present invention is a new compound. 1st
Representative compounds of the present invention are illustrated in the table.

EXAMPLES Next, the method for producing the compounds of the present invention will be explained in more detail by giving synthesis examples.

In a synthesis example, a solution of 13.2 g of sulfur chloride in 15rd dichloromethane was heated below 10°C to form 8.8 g of methyl N-methyl carbamate.
dropwise into a solution of 35 g of dichloromethane. After dropping, stir at 10°C or less for 1 hour, then add pyridine 10.1
A solution of 1-5 g of dichloromethane was added dropwise below 10°C. The mixture was allowed to stand at room temperature overnight, and then dry benzene was added and pyridine hydrochloride was removed by filtration. The solvent was distilled off, dry benzene was added, and pyridine hydrochloride was filtered off. After distilling off the solvent, 10.8 g of N-chlorosulfenyl-N-methylcarbamate (b, p, 73°C/22
mmHg) was obtained.

Synthesis Example 2 Synthesis of -4- C2-[3-chloro-5-(trifluoromethyl)pyridyloxy] 2.9 g of aniline and 1.2 g of triethylamine were dissolved in 15 ml of dry dichloromethane and the 1.6 g of the methyl N-chlorosulfenyl-N-methyl carbamate was cooled to 10
m1 dry dichloromethane solution was added dropwise. The mixture was continued to be stirred at room temperature for 2 hours, poured into cold water, extracted with dichloromethane, dried, and purified by column chromatography after distilling off the solvent. Further, the crude crystals were recrystallized from ether:hexane H:3) to obtain 2.6 g of the target product.
(m, p, 108-109°C) was obtained.

Synthesis Example 3 Methyl[4-C2-[3-chloro-5-(trifluoromethyl)]pyridyloxy]phenyl]-7-(2,6
-difluorophenyl)-2-memethyl CC(4-C2
1.26 g of -C3-chloro-5-(trifluoromethyl)[pyridyloxy]phenyl]amino]thio]-N-methylcarbamate was dissolved in 10- of dry benzene and 2.6- Cyfluoropenzoyl isocyanate) 0.53g of dry benzene 10rd! The solution was added dropwise. The mixture was stirred at room temperature for 3 hours, and after distilling off benzene, it was purified by flash column chromatography.
Furthermore, the separated target product is ether:hexane (1
:2) to obtain 0.87 g (m, p, 145-148°C) of compound No. 1.

The insecticide and acaricide of the present invention contains at least one or two or more compounds represented by the above general formula [E] as an active ingredient. Although the active ingredient compound can be used as is,
It can be formulated and used in the form of wettable powders, emulsions, powders, flowables, etc.

Next, specific formulation examples are illustrated, but the carrier, surfactant, etc. to be added are not limited to these formulation examples.

Formulation Example 1 Emulsion 20 parts of compound No. 5 was dissolved in 73 parts of xylene, 3.5 parts of polyoxyethylene alkyl allyl ether and 3.5 parts of alkylbenzene sulfonate were added as emulsifiers, and the whole was thoroughly mixed. Make it into an emulsion.

Formulation Example 2 Wettable powder Mix 30 parts of Compound No. 13 with 1 part of white carbon as a grinding aid and 63 parts of clay, and add 2 parts of higher alcohol sulfate and 4 parts of sodium lignin sulfonate as dispersing and wetting agents. Add and mix well, then
Grind and use as a hydrating agent.

These formulations are diluted with water to a certain concentration and distributed by conventional methods.

The compound of the present invention represented by the above general formula [■] not only has strong insecticidal power against various insect pests such as Lepidoptera, Diptera, Hemiptera, Coleoptera, etc., but also has strong insecticidal power against mites that parasitic animals and plants. It also has extremely high efficacy. In addition, it is a practical insecticide and acaricide that has excellent properties such as low toxicity to humans and livestock, low toxicity to plants, and low toxicity to fish. In addition to its larvicidal and ovicidal effects on larvae by inhibiting their molting, when it is applied to adults, it exhibits an irreversible effect that prevents the eggs they lay from turning into capes.

Examples of insect pests and mite necks for which the compound of the present invention is effective are as follows.

Lepidopteran pests: Spodoptera spp., Red-winged leafhopper, Golden leaf moth, Green caterpillar, Diamondback moth, Japanese green leaf beetle Hemi-winged pests: Black leafhopper, Red leafhopper, Green peach aphid, Red stink bug Coleopteran pests: Lady beetle, Rice weevil, Cucurbit beetle, Yellow leaf beetle Diptera Insects: house fly, Culex mosquito, seed fly, cowfly, mites: citrus spider mite, apple spider mite, two-spotted spider mite, red spider mite, two-spotted spider mite, tangerine four-spotted spider mite Next, the insecticidal and acaricidal effects of the compounds of the present invention will be shown by test examples.

Test Example 1 The wettable powder obtained in Formulation Example 2 was diluted with water to 5 ppm and 0.5 ppm, and the diluted powder was sprinkled on Chinese cabbage leaves. After air-drying, it was placed in a plastic container measuring 21 cm long x 13 cm wide x 3 cm deep, and 10 third instar larvae of Spodoptera japonica were released.The container was placed in a thermostatic chamber at 26°C, and after 5 days, the survival rate of the larvae was determined by checking whether the larvae were alive or dead (2 repetitions). The results are shown in Table 2.

Table 2 Table 2 (Continued) Experimental Example 2 A summer tangerine leaf piece cut into 2cm x 2cm pieces was placed with the underside facing up on filter paper moistened with water to prevent the leaf from drying out, and 10 tangerine spider mites per leaf piece were placed. Adult female worms were inoculated. The leaf pieces were left in a constant temperature room at 26° C. for 24 hours to lay eggs, then the adults were removed, and the leaves were allowed to develop into capes for another 3 days. The emulsion obtained in Formulation Example 1 was diluted with water to 500 ppm and soppm and sprayed on the larvae. After air-drying, the larvae were allowed to stand in a constant temperature chamber at 26°C, and after 5 days, the survival rate of the larvae was determined to determine the mortality rate (2 anti-ff). The results are shown in Table 3.

Table 3 Table 3 (Continued) Test Example 3 Cut a 30 m x 2 cm piece of green bean leaf and place it with the backside facing up on a filter paper moistened with water to prevent the leaf from drying out. Ten female Kanzawa spider mites were inoculated. The leaf pieces were left in a constant temperature room at 26° C. for 24 hours to lay eggs, then the adults were removed, and the leaves were allowed to develop into capes for another 3 days. The emulsion obtained in Formulation Example 1 was diluted with water to 5 ppm and 0.5 ppm, and
It was sprayed. After air-drying, the larvae were allowed to stand in a constant temperature chamber at 26°C, and after 5 days, the survival rate of the larvae was determined to determine the mortality rate (2 repetitions). The results are shown in Table 4.

Table 4 Table 4 (continued) In Tables 2 to 4, Comparative Compound A and ESC represent the following compounds.

Comparative Compound A (Diflubenzuron) Comparative Compound B Comparative Compound C ρ Effect The compound of the present invention represented by the general formula CI) has extremely high efficacy in controlling various insect pests and mites at a low dose. In addition, it has low toxicity to humans, livestock, and fish, and has little phytotoxicity to plants.

Procedural amendment 61.11.13 Showa year, month, day, Commissioner of the Patent Office, Kuro 1) Akio Tono 4 Ren 1,
Display of the case 1986 Patent No. 2386663,
Relationship with the case of the person making the amendment Applicant name Agro Kanesho Co., Ltd. 4, Agent 5, Date of amendment order Voluntary Table 2 (Continued)

Claims (5)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R represents a halogen atom, R_1 represents a halogen atom or a hydrogen atom, R_2 represents ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ , R_3 and R_4 is an alkyl group,
A benzoyl urea compound characterized by being represented by a cycloalkyl group or an aryl group. (2) The compound according to claim (1), wherein R is a chlorine atom and R_1 is a hydrogen atom, or R and R_1 are each a fluorine atom or a chlorine atom. (3) R_3 and R_4 each have 1 to 6 carbon atoms
The compound according to claim (1) or (2), which is an alkyl group, a cycloalkyl group having 3 to 6 carbon atoms, or a phenyl group. (4) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_ represents a halogen atom, R_1 represents a halogen atom or hydrogen atom, R_2 represents ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ , R_3 and R_4 is an alkyl group,
An insecticidal and acaricidal composition comprising a benzoyl urea compound represented by a cycloalkyl group or an aryl group as an active ingredient. (5) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R represents a halogen atom, R_1 represents a halogen atom or hydrogen atom, R_2 represents ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ , R_3 and R_4 is an alkyl group,
cycloalkyl group or aryl group) is used as it is or as an appropriate composition. A method for controlling pests and mites in the civil and veterinary fields.