JPS59212462A - Benzoylurea derivative and insecticide - Google Patents

Abstract

NEW MATERIAL:N-(2-Chlorobenzoyl)-N'-(3,5-dichlorophenyl)urea. USE:An insecticide having very high insecticidal activity against Plutella xylostella Linnaeus and armyworm, etc. PREPARATION:2-Chlorobenzoyl isocyanate is reacted with 3,5-dichloroaniline to give N-(2-chlorobenzoyl)-N'-(3,5-dichlorophenyl)urea. The reaction can be carried out if necessary in the presence of a solvent, e.g. benzene, toluene or xylene, within a relatively wide reaction temperature range, preferably within 0-150 deg.C range in general. The aimed substance can be obtained in high yield at about 10min-5hr reaction time.

Description

DETAILED DESCRIPTION OF THE INVENTION (Technical Field of the Invention) The present invention relates to a novel benzoyl urea conductor and an insecticide containing the same.

(Technical Background of the Invention) The damage caused to agricultural crops by pests is enormous, and the damage caused by diamondback moths and armyworms is particularly great, and a large amount of cost is spent on controlling these pests every year. On the other hand, in recent years, the emergence of pests that are resistant to existing drugs and the environmental pollution caused by commercially available drugs have become a problem, and new drugs that can effectively control pests with low doses and do not cause environmental pollution are needed. There is a strong demand for the development of

(Object of the invention) In view of the above technical background, the present inventors have
As a result of extensive research in order to develop a compound that has an extremely high insecticidal effect on armyworms, the present invention was completed by discovering that the compound of the present invention satisfies the above requirements.

(Prior art) So far, one formula (in the formula, A is a hydrogen atom, a halogen atom, a methyl group, or a methoxy group, and B is a hydrogen atom, 5 halogen atoms, a methyl group, or a methoxy group, provided that both A and B are hydrogen at the same time) It does not indicate atoms.

X and Y are each an oxygen atom or a sulfur atom.

R is a hydrogen atom, an alkyl group or an alkoxymethyl group, R' is a hydrogen atom, an alkyl group that may be substituted with cyan, a 1-cycloalkenyl group, a Hensyl group, a hydroxyl group,
Indicates an acetyl group or an alkoxycarbonyl group.

R2 is a pyridyl group, a 7-ethyl group, or a halogen-substituted pyridyl group, cyanide, nitro, alkyl, cycloalkyl, cycloalkyl substituted with halogen, alkylthio, alkoxy, alkylthioalkyl, trifluoromethyl, alkylsulfonyl, dialkylamino sulfonyl,
Compounds represented by phenyl, benzyl, phenylthio, halogen-substituted phenoxy, acetyl, phenylcarbonyl, or a ring formed by tetramethylene or dioxymethylene (indicating a substituted phenyl group) are known to be effective as insecticides. (Tokuko Sho 52-182)
．． 55 Publication Specification). However, what is specifically exemplified in the same specification is the halogen substitution positional force on the phenyl nucleus bonded to N[ζ, 2-, 3-, 4-.

2.5-, 2.6-. 5.4-, 2.4, 5-, and 6
, 4°5-. In addition, the same specification iK states that those having one or two substituents at the 6-position, 4-position, or 6 and 4-positions of the phenyl group have the highest activity, but the 3-, 5-position of the present invention Compounds in which chlorine is substituted with are not described.

(Structure of the Invention) The benzoyl urea derivative according to the present invention is N-(2-chlorobenzoyl)-N'-(3,5-dichlorophenyl)urea.

The compound of the present invention can be produced by reacting 2-chlorobenzoyl isocyanate and 6,5-dichloroaniline. The reaction can be carried out in the presence of a solvent if necessary. Examples of solvents include aromatic hydrocarbons such as benzene, toluene, and xylene, and dichloromethane.

Aliphatic and aromatic halogenated hydrocarbons such as chloroform, carbon tetrachloride, and chlorobenzene.

Ethers such as ether, dioxane and tetrahydrofuran, and nitriles such as acetonitrile.

Ketones such as acetone and methyl ethyl ketone.

Amides such as N,N-dimethylformamide and N,N-dimethylacetamide, dimethylsulfoxide, and the like can be used. The reaction temperature can vary within a fairly wide range, but a range of 0 to 150°C is generally preferred. If the reaction time is about 10 minutes to 5 hours, the desired product can be obtained in good yield. It is also a raw material.

2-Chlor benzoyl isocyanate.

It can be produced by a known method using 2-chlorobenzamide and oxalic acid chloride.

The compound of the present invention can also be produced by reacting 2-chlorobenzamide with 6,5-dichlorophenylisocyanate. The reaction can be carried out in the presence of a solvent if necessary. As the solvent, those described in the above reaction can be used. Furthermore, the reaction can be accelerated by adding a tertiary amine such as triethylamine as a catalyst.

The reaction temperature is preferably in the range of 0 to 750°C.

If the reaction time is 2 to 6 hours, the desired product can be obtained in good yield. It can be produced by a known method from 6,5-dichlorophenylisocyanate and 5,5-dichloroaniline as raw materials.

(Preparation Examples) Next, the method for producing the compound of the present invention will be explained in detail using reference examples.

Reference Example I N-(2-chlorobenzoyl)-N'-(
6,5-dichloroaniline of 3,5-dichlorophenyl)urea 4.97 (0.03 mol)
was dissolved in toluene 5QmA and stirred therein.

A solution of 2-chlorobenzoyl incyanate in 50 titolene (10,03 moles) is added dropwise.

After the addition was completed, the mixture was further stirred at room temperature for 6 hours.

Next, the precipitated crystal YF is collected, washed with n-hexane, and dried to obtain the desired N-(2-chlorbear soil).
N'-(s,5-dichlorophenyl)urea with a melting point of 20
95 min as white needle crystals at 7-208°C (yield 92.2
%)obtain.

Reference fB N-(2-chlorobenzoyl)-N-(3
, 5-dichloropheni)urea (compound-1) 6. 5-dichloroenylthiocyanate y, 5
y (o, 04 mol) and 2-chloropenzamide 6,27 (0.04 mol) in dry toluene 100I
+ItVc is dissolved and stirred under reflux for 5 hours. From now on, when the precipitate is quenched and washed with n-hexane, the desired N-(2-chlorobenzoyl)-N-(3,5-dichlorophenyl)urea can be obtained as a white powder with a melting point of 207-208°C. 112 as a colored needle-like product? (yield 81.8%).

Moreover, one insecticide of the present invention is only one compound of the present invention.

Alternatively, it can be formulated into various forms such as wettable powders, emulsions, granules, powders, etc. by blending it with various carriers, surfactants, dispersants, adjuvants, etc. that are commonly used in the formulation of agricultural chemicals.

When used, it is diluted to an appropriate concentration and sprayed, or applied directly. (Formulation Examples) Next, we will explain formulation examples of the insecticide of the present invention. Needless to say, it is not limited to , and can be changed within a wide range. In the following formulation examples, all parts indicate parts by weight.

Formulation Example 1 (Wettable powder) 20 parts of the compound of the present invention, 35 parts of diatomaceous matter, 35 parts of clay, 5 parts of white carbon, 6 parts of Nucor 564 (Nippon Nyukazai ■ registered trademark).

Sunextract P252 (Sanyo Kokusaku Pulp ■registered trademark name) 2
Mix and pulverize a portion to make a wettable powder.

Example 2 (Emulsion) 22 parts of the compound of the present invention, 63 parts of dimethyl sulfoxide, Nucalgen STso (Registered trade name of Monomoto Yushi)
1 part of the compound of the present invention, 49 parts of talc, 47 parts of clay, and 3 parts of white carbon are mixed and ground to obtain a powder. When using, just scatter 8F.

(Effects of the Invention) The compound of the present invention has extremely high insecticidal activity v+IL compared to the compound specifically described in the specification of Japanese Patent Publication No. Sho 52-18255, and is useful as an insecticide.

The harmful history that can be effectively controlled by the insecticide of the present invention includes the following.

Paddy rice pests 2. Pests of field crops: Japanese armyworm, fall armyworm, Japanese caterpillar, Japanese caterpillar.

Tea pests: Chakokakumon hamaki, Chabamaki fruit tree pests: Kokakumon no 1maki, peach beetle, goldenrod spider mites: Citrus paper mite, Namino snail mite, false worm mite, Kanzawa hatani, apple spider mite Major pests: House fly, Shikiji hon The effects of the invention compound 1ri1 will be explained using test examples. In addition, comparative compound 1 and comparative compound ■ in the table
is a compound described in Japanese Patent Publication No. 52-18255 and has the following structure.

Comparative compound I N-(2-chlorobenzoyl)-N
”-(3,4-dichlorophenyl)urea comparison compound [N-(2,6-difluorobenzoyl)-
N'-(4-Chlorphenyl) Urea Test Example 1 (Insecticidal power against Spodoptera trifoliata) Formulation Example 1
A hydrating powder of the compound of the present invention prepared according to the above method was diluted with water. Next, the silkworm artificial feed was cut into pieces about 5 U thick. The feed pieces were soaked in the chemical solution and placed in a 60 cc PVC cup lined with paper. , released five 3rd instar larvae of Spodoptera japonica there,
The specimens were stored in a constant temperature room at 25°C and examined for dead types and abnormal numbers of insects after 8 days. The test was conducted in two replicates per section, with 10 animals tested. The results are shown in Table iVC.

Table 1 One day after inoculating soybeans planted in 25-inch pots with egg masses of 3rd instar Spodoptera larvae, the aqueous phase agent of the compound of the present invention prepared according to Formulation Example 1 was sufficiently sprayed with a spray gun and placed in a greenhouse. .

Four days after spraying, the number of live and dead animals was investigated. The test was conducted with 3 repetitions per section. The test results are shown in Table 2.

Table 2 Test Example 3 Efficacy against Diamondback Moth Preparation Examples 1 & C The aqueous phase preparation of the compound of the present invention prepared according to the above procedure was diluted, and cabbage leaves were immersed in this drug solution.

After air-drying, it was placed in a 60CC PVC cup, and 3rd instar diamondback moth larvae were released into it and stored in a constant temperature room at 25°C. After 14 days, the number of adults was counted.

The test was conducted with 20 animals, 5 animals per ward.

The test results are shown in Table 3.

Table 6

Claims (1)

[Claims] (IIN-(2-chlorobenzoyl)-N'-(S,
5-dichlorophenyl)urea (21N-(2-chlorobenzoyl) -N'-(3,
An insecticide characterized by containing urea (5-dichlorophenyl).