JPS60193960A - N-benzoyl-n'-phenylurea compound and insecticide containing same - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [X is H or halogen; Y is halogen; Z is 2,6-(or 3,5-)dichloro-3,5-(or 2,6-)difluorophenyl, 3,5-dichloro-2,4,6-trifluorophenyl, etc.]. EXAMPLE:N-(2,6-Difluorobenzoyl)-N'-(2,6-dichloro-3,5-difluorophenyl)-u rea. USE:An insecticide. Useful especially for the control of noxious vermin. PREPARATION:The compound of formula I can be prepared by reacting the compound of formula II (R<1> is carbamoyl or isocyanatocarbonyl) with the compound of formula R<2>-Z (when R<1> is carbamoyl, R<2> is isocyanato, and when R<1> is isocyanatocarbonyl, R<2> is amino) in a solvent such as methylene chloride at 0-100 deg.C.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel N-benzoyl-N'-phenylurea compounds and insecticides containing them.

Specifically, the present invention is based on the general formula CI) (wherein X is a hydrogen atom or a halogen atom, Y is a halogen atom, and Z is a 2,6-dichloro-3,5-difluoro7enyl group, 3,5-dichloro-2,6-difluoro7-el group, 2,4-dichloro-3,5-difluorophenyl group, or 3,5-dichloro-2,4,rotrifluorophenyl group) N-benzoyl-N'-phenylurea compounds and insecticides containing them.

Examples of the halogen atoms represented by X and Y in the general formula (I) include fluorine, chlorine, bromine, and iodine.

The N-benzoyl-N'-phenylurea compound of the present invention usually has the general formula [■] (wherein X and Y are as described above, and R1 is a carbamoyl group or incyanatocarbonyl group). A compound represented by the general formula (III) 2-Z (I[) (wherein Z is as described above, R2 is an incyanato group when R1 is a carbamoyl group, and when R1 is an isocyanatocarbonyl group It is produced by reacting a compound represented by amine 7 group). This reaction is effective for aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; chloroform, carbon tetrachloride,
Cyclic or acyclic aliphatic hydrocarbons such as methylene chloride, dichloroethane, trichloroethane, hexane, cyclohexane, and ethyl acetate; Ethers such as diethyl ether, dioxane, and tetrahydrofuran; Ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; Ni dimethyl sulfoxide The reaction temperature is 0 to 100'C1 and the reaction time is 0.1 to 24 hours.

Next, specific synthesis examples of the compounds of the present invention will be described.

Synthesis Example I N-(2,6-difluorobenzoyl)-N
Synthesis of -(2,4-di90-3,5-difluorophenyl)urea (1) 5.0 g of 3,5-dichloro-2,4,6-)lifluorobenzonitrile and 100 m of 28% ammonia water
ff was added while cooling, and then the reaction was allowed to proceed at room temperature for 15 hours with stirring.

After the reaction was completed, the precipitated crystals were filtered, dissolved in methylene chloride, dried over anhydrous sulfur, and the solvent was distilled off under reduced pressure.
The residue was separated by silica gel column chromatography,
0.97 g of 2-amino-3,5-dichloro-4,6-cyfluorobenzonitrile and 2.4 g of 4-amino-3,5-dichloro-2,6-cyfluorobenzonitrile were obtained.

(2) 70% of 3.7 g of 2-7 minnow 3,5-dichloro-4,6-cyfluorobenzonitrile obtained in (1) above
It was dissolved in 30 mρ of sulfuric acid and reacted at 150 to 160°C for 3 days with stirring. After the reaction was completed, the product was poured into ice water, extracted with methylene chloride, and the extracted layer was dried over anhydrous nitric acid, the solvent was distilled off under reduced pressure, and the product was separated by silica gel column chromatography to give a melting point of 62-63.5°C. 1.12 g of 2,4-dichloro-3,5-difluoroaniline was obtained.

(3) To 0.88 g of 2,4-dichloro-3,5-difluoroaniline obtained in (2) above, 1.0 g of 2,6-cyfluorobenzoyl isocyaner) and 15 ml of dioxane
The mixture to which 2 was added was allowed to react at room temperature for 14 hours with stirring. After the reaction was completed, the product was poured into water, filtered, and washed with hot water and ethyl acetate to obtain 0.98 g of the desired product having a melting point of 237-241°C.

Specific representative examples of compounds produced according to the general production method and specific synthesis examples described above will be described.

Compound No, I N-(2,6-difluorobenzoyl)-N'-(2,6-dichloro-3,5-difluorophenyl)urea m, p, 180.5-183°C Compound No, 2 N-( 2,6-difluorobenzoyl)-N
'-(3,5-dichloro-2,6-difluoro7enyl)urea m, p, 210-214'C compound No.
3 N-(2,6-difluorobenzoyl)-N'-
(2,4-dichloro-3,5-difluorophenyl)urea m, p, 237-241°C Compound No., 4 N-
(2,6-difluorobenzoyl)-N'-(3,5
- Fukuroro 2, 4.6. -trifluorophenyl)urea, p, 207-211°C Compound No. 5, N-(2-chlorobenzoyl)-N
' -(2,4-dichloro-3,5-difluorophenyl)urea m, p, 241-245°C As shown in the test examples below, the compound of the present invention is excellent as an active ingredient of insecticides, especially insecticides. Shows activity.

When this product is used as an active ingredient of an insecticide, it can be formulated into various forms such as an emulsion, a powder, a wettable powder, a liquid, etc. together with an agricultural chemical auxiliary, as in the case of conventional agricultural chemical formulations. When these preparations are actually used, they can be used as they are, or they can be diluted to a predetermined concentration with a diluent such as water. The pesticide adjuvants mentioned here include solid carriers such as tar, kaolin, bentonite, diatomaceous earth, white carbon, clay, and starch, water, toluene, xylene, chlorobenzene, cyclohexane,
Examples include liquid diluents such as dimethyl sulfoxide, dimethylformamide, and alcohol, emulsifiers, dispersants, and spreading agents. Furthermore, if necessary, it can be mixed or used in combination with other agricultural chemicals such as insecticides, acaricides, fungicides, plant growth regulators, etc. In this case, even more excellent effects may be exhibited.

The insecticide of the present invention is effective in controlling various harmful insects, especially harmful insects, and the application is generally o, ooi to 1+OOOOpp.
m, preferably at an active ingredient concentration of 0.01 to 500 ppI11. It is also possible to feed livestock with the above-mentioned active ingredients mixed with their feed to control the emergence and growth of harmful insects, especially harmful insects, in their wandering materials, or by treating adult insects with the active ingredients. It also ends up preventing the eggs from hatching. In the case of harmful aquatic insects, it is possible to control them by spraying a chemical solution in the above concentration range to the place where they occur, so it is effective even if the concentration range of the chemical solution in water is less than the above range.

Next, test examples of the insecticide of the present invention will be described.

Test Example 1 A preparation of an active ingredient compound was dispersed in water, and cabbage leaves were immersed in a drug solution adjusted to a concentration of 50 ppm for about 10 seconds, taken out, and air-dried. Petri dish (diameter 9cI+1)
A damp filter paper was placed on top of the filter paper, and the leaf pieces were placed on top of it. There 2
~ Release 3rd instar Spodoptera larvae and cover with a lid.
It was left in a lighted thermostat at °C. The survival rate was determined on the 8th day after the release of the insects, and the survival rate was calculated using the following formula to obtain the results shown in Table 1.

Number of dead insects and stopping rate (%) = -X 100 Table 1 Compound No. after release, killing rate (%) 1 100 2 100 3 100 4 100 5 100 Test example 2 Two to three instars of Spodoptera The test was conducted in the same manner as in Test Example 1 above, except that the three-instar three-year-old Funagas were hatched, and the results shown in Table 2 were obtained.

Table 2 Compound No. Stopping rate (%) 1 100 2 100 3 100 4 100 5 100 Test Example 3 Approximately 250 mff of the chemical solution of compound No. 3 adjusted to a concentration of 1 opppb was placed in a deep-bottom petri dish with a diameter of 9 cm. Third instar Chikae mosquito larvae were released and placed in a lighted incubator at 28°C with a lid on. As a result of examining the survival of the larvae on the 10th day after they became adults, a 100% survival rate was observed.

Next, formulation examples of the insecticide of the present invention will be described.

Formulation Example 1 Compound No. 2 20 parts by weight (b) Di-Cryte 72 parts by weight (c) Sodium ligninsulfonate 8 parts by weight or more were uniformly mixed to prepare a wettable powder.

Formulation example 2 (a) Compound No. 4 5 parts by weight (b) Talc 95 parts by weight The above ingredients were mixed uniformly to form a powder.

Formulation Example 3 (a) Compound No. 5' 20 parts by weight (b) N, N'
- 70 mt parts of dimethylformamide (c) 10 parts by weight or more of polyoxyethylene alkylphenyl ether were uniformly mixed and dissolved to form an emulsion.

Formulation Example 4 (a) Di-cryte 78 parts by weight (b) 2 parts by weight of β-7talenesulfonic acid sodium formalin complex (c) 5 parts by weight of polyoxyethylene alkylaryl sulfate (d) White carbon 15 parts by weight A mixture of 1 part or more of each component and Compound No. 3 were mixed at a weight ratio of 4:1 to prepare a wettable powder.

Procedural amendment (method) % formula % 1, Indication of case Patent Application No. 50091 of 1982 2,
Title of the invention N-benzoyl-N'-phenylurea compounds and insecticides containing them 3. Relationship with the case of the person making the amendment Patent applicant 5. Subject of the amendment Full text of the specification 6. Contents of the amendment As attached. (Type-printed procedural amendment by Manabu Shiga, Director General of the Japan Patent Office 1, Indication of the case, Patent Application No. 50091 of 1982, 2)
Title of the invention N-benzoyl-N'-phenylurea compounds and insecticides containing them 3. Relationship with the case of the person making the amendment Patent applicant 6. Contents of the amendment (1) Page 4 of the specification, 5 from the bottom Correct "anhydrous salt" to "anhydrous salt" in line 5 and page 5, line 5.

(2) “Excrement” on the seventh line from the bottom of the specification is “Wandering”.
Corrected to "t thing".

Claims (1)

[Claims] 1. General formula (wherein X is a hydrogen atom or a halogen atom, Y is a halogen atom, Z is a 2,6-dichloro-3,5-difluorophenyl group, 3.5- N-benzoyl- represented by dichloro-2,6-difluorophenyl group, 2,4-dichloro-3,5-difluorophenyl group or 3,5-dichloro-2,4,64-difluorophenyl group) N'-7! Unilurea compound%. 2. General formula (wherein X is a hydrogen atom or a halogen atom, Y is a halogen atom, Z is a 2,6-dichloro-3,5-difluorophenyl group, 3,5-dichloro-2,6- N-benzoyl-N'-phenylurea represented by a difluorophenyl group, a 2,4-dichloro-3,5-difluorophenyl group, or a 3,5-dichloro-2,4,6-)lifluorophenyl group) An insecticide characterized by containing at least one type of compound as an active ingredient.