JPS59212463A - Benzoylurea derivative and insecticide - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (X is Cl or F; Y is H or F; A is straight chain or branched alkylene or alkenylene; R is alkyl or alkynyl). EXAMPLE:N-(2-Chlorobenzoyl)-N-{3,5-dichloro-4-(2-ethoxyethoxy)phenyl}u rea. USE:An insecticide having improved insecticidal effect particularly on tobacco cutworm, Plutella xylostella Linnaeus and green caterpillars, etc. PREPARATION:A benzoyl isocyanate derivative of formula II is reacted with an aniline derivative of formula III. The above-mentioned reaction is preferably carried out in the presence of a solvent, e.g. benzene, toluene or xylene. The reaction is advanced more easily by adding an organic base, e.g. triethylamine or pyridine, as a catalyst.

Description

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

(Technical Background of the Invention) The damage caused to agricultural crops by various pests of yuzu is severe, and the damage caused by fall armyworms, diamondback moths, blue-bellied moths, nikkamei chuku, etc. is particularly severe, and a large amount of control costs are required every year to control these pests. It has been invested.

On the other hand, in recent years, insect pests that are resistant to existing drugs have appeared.

Alternatively, environmental pollution caused by commercially available drugs has become a problem, and there is a strong demand for new drugs that can effectively control pests with low doses and are free from environmental pollution.

(Object of the Invention) In view of this demand, the present inventors conducted intensive research and found that the compound of the present invention solves the above-mentioned problems.
This completes the present invention.

(Prior art) As a benzoyl urea compound, diflubenzuron (
cliflubenzuron) has already been commercially available as an insecticide; however, the compound of the present invention has a particularly superior insecticidal effect against Lymphoptera pests such as Spodoptera spp., mealybugs, and green caterpillars, compared to this commercially available drug.

(Structure of the Invention) The benzoyl urea derivative according to the present invention has the general formula (wherein,
X represents a chlorine atom or a fluorine atom, Y represents a hydrogen atom or a fluorine atom, A represents a linear or branched alkylene group or an alkenylene group, and R represents an alkyl group or an alkenyl group. )
I was made to look after her.

Referenced in the following description.

Table 1 The compounds of the present invention can be produced by the following method.

(1) A benzoyl incyanate derivative represented by the general formula (wherein X and Y are as described above) and a benzoyl incyanate derivative represented by the general formula (wherein A and R are as described above) React with aniline derivative.

The above reaction is preferably carried out in the presence of a solvent, such as aromatic hydrocarbons such as benzene, toluene/xylene, halogenated hydrocarbons such as chloromethane and chloroform, and ketones such as acetone and methyl ethyl ketone. kind,
Organic bases such as pyridine, ethers, ethers such as dioxa/N,N-dimethylformamide), N,N
- Aprotic polar solvents such as dimethylacetamide, acetonitrile, dimethyl sulfoxide can be used. Furthermore, by adding an organic base such as triethylamine or pyridine as a catalyst, the reaction can proceed more easily. The reaction temperature is 10-140°C and the reaction time is
If the reaction is carried out for 30 minutes to 20 hours, the desired compound of the present invention can be produced in high yield.

The raw material benzoyl isocyanate can be produced from benzamide and oxalic acid chloride by a known method.

In addition, the compound of the present invention (9) is a benzamyl derivative represented by the general formula (wherein, It can also be produced by reacting with an isocyanate derivative represented by:

The reaction can be carried out under conditions similar to those described above.

The raw material phenyl isocyanate derivative can be produced from the corresponding aniline-decorated conductor and phosgene by a known method.

(Manufacturing example) Next, specific production examples of the compounds of the present invention will be described.

(Production Example 1) Production of N-(2-chlorobenzoyl)-N・-(3,5-dichloro-4-(2-ethoxyethoxy)phenyl)urea s, s-Cycloro-4-(2-ethoxyethoxy) )
Add 1.1y (4.4 mmol) of aniline to 20% of toluene.
A solution prepared by dissolving 0.9 f (5 ml) of 2-chlorobenzoyl isocyanate in 1 rLl of toluene was added dropwise to this solution under stirring, and the reaction was carried out at room temperature for 3 hours. After the reaction was completed, toluene was distilled off, the residue was crystallized, and further washed with cold toluene and n-hexane in order, and after drying, xi-(2-chlorobenzoyl)-N'-
(3,5-cyclo-4-(2-ethoxyethoxy)phenyl)urea to, f was obtained. (Yield 52.6%, melting point 121-123°C) (Production Example 2) N-(2,6-difluorobenzoyl) -N' -(
Preparation of 3,5=dichloro-4-(2-ethoxyethoxy)phenyl)urea 3.5-dichloro-4-(2-ethoxyethoxy)aniline 1.3F (5 mmol) was mixed with toluene 201R1
2.2 f (6 mmol) of a toluene bath solution of 50% 2.6-cyfluorobenzoyl incyanate was added dropwise under stirring, and the reaction was carried out at room temperature for 2 hours. After the reaction, toluene was distilled off under reduced pressure and the residue was crystallized, washed successively with cold toluene and n-hexane, dried, and N-(
1.32 of 2,6-difluorobenzoyl)-H'-(3,5-dichloro-4-(2-ethoxyethoxy)phenyl)urea was obtained.

(Yield: 60.0, melting point: 90-93°C) The insecticide of the present invention may contain only the two compounds of the present invention, or each of the carriers, surfactant, dispersant, and auxiliaries commonly used in the formulation of agricultural chemicals. Mixing drugs etc.

It is formulated into various forms such as wettable powders, emulsions, nine grains, and powders. When using it, dilute it to an appropriate concentration and spray it.
Also apply directly.

(Formulation Examples) Next, formulation examples of the insecticide of the present invention will be explained.
The type and blending ratio of oral preparations are not limited to these, and may be varied within a wide range at any time. In the following formulation examples, all parts indicate heavy parts.

Formulation Example 1 (Aqueous phase agent) Compound + 312 n parts, 35 parts of chilium earth, 35 parts of clay
1 part, white carbon, 6 parts of Newcoal 564 (Nippon Nyukazai Co., Ltd. → registered name), and 2 parts of Sunextract P252 (Sanyo Kokusaku Pulp ■ registered name) were mixed and ground to make a wettable powder.

Formulation Example 2 (Emulsion) Compound t2122 (JIS, 66 parts of dimethyl sulfoxide.

Ni Calgen 5T50 (Takemoto Yushi ■registered trademark name) 15
A portion is uniformly dissolved in a bath to form an emulsion.

Formulation example 6 (powder) Compound (1) 1 evil, Merck 49 parts, Clay 47 parts.

Mix and crush 3 parts of white carbon to make a powder.

When using it, simply sprinkle it with powder.

(Effects of the Invention) The compound of the present invention has extremely higher insecticidal activity than the commercially available drug siflubenzuron, and is useful as an insecticide. By the insecticide of the present invention.

The following are controversial as harmful insects that can be effectively controlled.

Paddy rice pests, the two-spotted caterpillar moth.

rice beetle, rice weevil 1 [Insects Two Hasmon Spodoptera, Armyworm, Tips and Tricks.

Green caterpillar, Kumanakin Uwaba tea! Insects: Chakokakumonhamagi, Nayahamaq Fruit tree pests: Kokakumonhamagi, Momosink 1 insect.

Cotton pests: Heliothis, Paul Quiffle sanitary pests:
Housefly, 77 Next, the young fruit produced by the compound of the present invention will be explained using test examples.

Test Example 1 (Insecticidal power against Konaka) A wettable powder of the compound of the present invention prepared according to Formulation Example 1 was diluted with water, and cabbage leaves were immersed in this chemical solution.

After air-drying, it was placed in a 60CL vinyl chloride cup and 6th instar larvae of the diamondback moth were released therein, stored in a constant temperature room at 25°C, and the number of adults was counted after 14 days. The test was conducted on five animals in one ward. The test results are shown in Table 2.

Table 2 A wettable powder of the compound of the present invention prepared according to Formulation Example 1 was diluted with water and then cut into pieces about 5 mm thick for silkworm artificial feed.
0) Feed pieces were soaked in mulberry and placed in a 6nCG vinyl chloride cup lined with 14 ounces of paper.

B heads of 6th instar larvae of P. japonica were released and stored in a constant temperature room at 25°C, and after 8 days, the dead weight and abnormal weight were examined.

The experiment was conducted with 5 animals in each ward and 10 animals were tested. The test results are shown in Table 6.

Table 6

Claims (2)

[Claims] (1) General formula % Formula % (In the formula, or a chlorine atom or a fluorine atom, Y is a hydrogen atom or a fluorine atom, A is a straight chain or branched alkylene group or an alkenyl group, and R is an alkyl group or an alkenyl group. A benzoyl urea derivative represented by (2) General formula (wherein, X represents a chlorine atom or a fluorine atom, Y represents a hydrogen atom or a fluorine atom, A represents a linear or branched alkylene group or an alkenylene group, and R represents an alkyl group or an alkenyl group. ) An insecticide containing a benzoyl urea derivative represented by the following as an active ingredient.