JPS6051163A - Benzoylurea derivative and insecticide - Google Patents

Abstract

NEW MATERIAL:The compound of formula I (R<1> is H or halogen; R<2> is halogen; R<3> is H, halogen or trifluoromethyl; R<4> is H or halogen; R<5> is H or lower alkyl; R<6> is halogen, nitro or trifluoromethyl; n is 0-2). EXAMPLE:N-(2,6-Difluorobenzoyl)-N'-[4-(3,5-dichloroanilino)phenyl]urea. USE:Insecticide and miticide. It exhibits excellent insecticidal activity especially against diamondback moth and night crawler. PREPARATION:The compound of formula I can be produced by reacting the benzoyl isocyanate derivative of formula II with the aniline derivative of formula III optionally in a solvent (e.g. toluene, chloroform, etc.) at 0-150 deg.C for 10min-5hr.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention (1) relates to a novel benzoyl urea derivative and an insecticide containing the same.

Agricultural crops are seriously damaged by various insect pests, especially by diamondback moths and armyworms (huge amounts of money are spent every year to control these pests).
In recent years, the appearance of insect pests that are resistant to existing drugs and the environmental pollution caused by commercially available drugs have become a problem, and there is a need for the development of new drugs that can effectively control pests with low dosage and are free from environmental pollution. ing.

In view of these demands, the present inventors conducted intensive research to develop a compound that has an extremely high insecticidal effect against the armyworms and armyworms, and as a result, they found that the compound of the present invention satisfies the above requirements, and completed the present invention. This is what I did.

Until now, N-(2-chlorobenzoyl)-N'-[3
-Chlor-4-(4'-chlorphenylamino)phenyl]urea (hereinafter referred to as comparative drug 1) and N-(2,6-
cyfluorobenzoyl)-N'-(3-ri-o-ru-4-
It is known that (4'-chlorophenylamino)enyl]urea (hereinafter referred to as comparative drug 2) is effective as an insecticide and acaricide (Japanese Patent Application Laid-Open No. 74655/1983). In addition, diflubenzuron is commercially available as a benzoyl urea compound, but the compound of the present invention has excellent insecticidal effects against cyclopteran pests such as diamondback moth and Spodoptera nigra, even when compared with known and commercially available drugs. be.

The benzoyl urea derivative according to the present invention is a general R゛ (in the formula, R1 is a hydrogen atom or a halogen atom, N' is a halogen atom, R'' is a hydrogen atom, a halogen atom, or a trifluoromethyl group, and R4 is a hydrogen atom or A halogen atom, R1 is a hydrogen atom or a lower alkyl group, and R6 is a hydrogen atom or a lower alkyl group.
or a different halogen atom, nitro group or trifluoromethyl group, n is an integer of 0.1.277). however,
R@ cannot be a single substitution of chlor at the 4th position of the pentcene nucleus. ).

Next, the compound represented by the general formula (1) of the present invention and its physical properties will be shown. Compound numbers are referenced in the following description.

Melting point 214-216°C Melting point 213-215°C Y Chest-'+-'+ 2+G~2'? ``0'' The unexploded horn compound can be produced by the method given by the following formula 16.

Reaction formula (1) (In the formula, 1 (1 to R6 and n have the same meanings as above) In this method, !811 is produced by reacting a benzoyl isocyanate derivative and an aniline derivative. If necessary, it can be carried out in the presence of a solvent. Examples of solvents include aromatic hydrocarbons such as benzene, toluene, and xylene, dichloromethane, chloroform,
Aliphatic and aromatic halogenated hydrocarbons such as carbon tetrachloride and chlorobenzene, ethers such as ether, dioxane and tetrahydrofuran, and nitriles such as acetonide 1,1l.

Ketones such as acetone and methyl ethyl ketone, N.

Amides such as N-dimethylformamide and N,N-dimethylacetamide, dimethyl sulfoxide, and the like can be used. The reaction humidity can be varied within a fairly wide range;
Generally, a range of 0 to 150°C is preferred. The reaction time is 10
The desired product can be obtained in good yield if the reaction is allowed to proceed for about 5 hours.

The raw material, the penzoylisonite derivative, can be produced from the corresponding benzamide and oxalic acid chloride by a known method. The aniline derivative as the first raw material can be produced by reacting a 4-chloronitrobenzene derivative with an aniline derivative to obtain a 4-anilinonitrobenzene derivative, and further reducing the nitro group to an amine group.

Reaction formula (II) (in the formula, R1 to R@ and n have the same meanings as above)
In this method, it is produced by reacting a benzamide derivative and a phenyl isocyanate derivative. The reaction can be carried out in the presence of a solvent if necessary. As the solvent, the one obtained by formula (I) above 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 150°C. If the reaction time is 2 to 6 hours,
Yield (the target product can be obtained.

The raw material phenyl isocyanate derivative can be produced from the corresponding aniline derivative by a known method.

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

Reference Example I N-(2,6-difluorobenzoyl)-N
Production of '-4-(3,5-dichloroanilino)phenylurea (compound? I2) 4-(5,5-dichloroanilino)aniline Z6f
(0.03 mol) was dissolved in 80 m/m of toluene and
While stirring, 11.0f (0.03 mol) of a 50% toluene bath solution of 2,6-cyfluoropensoyl incyanate was added dropwise. Crystals precipitate immediately upon dropping. After the dropwise addition was completed, the mixture was further stirred at the same temperature for 1 hour to complete the reaction. The precipitate was collected and washed with n-hexano to a melting point of 23.
12.5 F as a white powder with a temperature of 5 to 267°C
(yield 95.4%).

Reference example 2N-(2-chlorobenzoyl) N#-4-(
Production of 2,4-dichloroanilino)-6-dolifluoromethylphenylurea (compound 4) 4-(2,4-dichloroanilino)-5-1-lifluoromethylaniline 6,4 f 40.02 mol) A 50% toluene solution Z2 of 2-chlorobenzoyl isocyanate was dissolved in 50ml of toluene and stirred at room temperature.
t (0.02 mol) is added dropwise. After the addition was completed, the mixture was further stirred for 2 hours and then treated in the same manner as in Reference Example 1 to give a melting point of 151 to 1.
The desired product was obtained at 54°C as an orange powder of 85f (yield: 842 tin).

Harmful insects that can be effectively controlled by these compounds of the present invention include the following.

Rice pests Pests of field crops: Japanese armyworm, fall armyworm, rice beetle, and rice beetle.

A, A-mun, Tamanagin Uwabacha Pests: Chanokorikokumonhamaki, Chabamaki fruit tree beneficial insects: Kokakumonhamaki, Shichimonnkubee.

Kinmonhosoga Cotton pests: Heliotis C ball, worm).

Ball, Raipur Sanitary Pests: Housefly, Pest The compound of the present invention has low toxicity and co-occupation with crops.
It is useful as a good and highly safe insecticide.

Next, (1) the insecticide of the present invention contains the compound of the present invention as an active ingredient; (2) the compound of the present invention alone or mixed with various auxiliary agents (1) such as diluents, solvents, surfactants, etc., to form an emulsion; It can be formulated and applied in the form of wettable powders, powders, etc.

Examples of diluents include clay, talc, bentonite,
Examples of solvents include diatomaceous earth and white carbon, and examples of solvents include xylene, toluene, methyl ethyl ketone, isopropanol, dimethylnaphthalene, and dimethylformide. Examples of surfactants include "alkylbense) I/metal phonate, polyoxyethylene alkyl allyl needle, alkyl sodium sulfate,
Examples include rukynaphthalene sulfonic acid sorta, ') kuninsulfonic acid soda, and the like.

Next, examples of formulations of the insecticide of the present invention will be explained, but the rights and compounding ratios of additives are not limited to these (it goes without saying that they have a wide range of effects). In the following formulation examples, all parts indicate parts by weight.

Formulation example 1 (emulsion) Compound fi+ 40 parts, dimethylformamide 50 parts.

Uniformly dissolve 10 parts of Tsurupol 5NX (registered trademark of Toho Chemical Industries) to make an emulsion ◇Formulation example 2 (wettable powder) Compound + 2120 parts, 35 parts of clay, 35 parts of clay, 5 parts of white carbon, New A wettable powder was prepared by mixing and pulverizing 6 parts of Cole 564 (Nippon Nyūkazai ■registered trademark name) and 2 parts of Sunextract P252 (Sanyo Kokusaku Pulp ■registered trademark name).

Next, the effects of the compounds of the present invention will be explained using test examples.

Test Example 1 (Insecticidal power against diamondback moth) A wettable powder of the compound of the present invention prepared in accordance with Formulation Example 2 was diluted with water, and cabbage leaves trapped in this drug solution were immersed. After air drying, put it in a +60oo vinyl chloride cup.

Release the 3rd instar larvae of the diamondback moth into SoC and store it at a constant temperature of 25°C.
After 10 days, the number of normally emerged insects was examined. The test consisted of two repetitions with 10 animals per section and 20 animals. The test results are shown in Table-1〇Table-1 Test Example 2 (Prevention effect on Spodoptera japonica) 2.5
A soybean planted in a small pot was clasped with egg masses of Spodoptera japonica, which had just been planted, and one day later, a chemical solution prepared by diluting a hydrating agent of the compound of the present invention prepared according to Formulation Example 2 with water was sufficiently sprayed with a spray gun, and the mixture was placed in a greenhouse. Ta.

Four days after spraying, the number of live and dead insects was investigated, and dead appendices were removed.

The test was conducted in 1 group and 3 times. The test results are shown in Table-2.

Table-2

Claims (1)

[Claims] (In the formula, R1 is a hydrogen atom or a halogen atom, I is a halogen atom, R'' is a frozen candy atom, a halogen atom, or a trifluoromethyl group, and R4 is a hydrogen atom or a halogen atom. (F is a hydrogen atom or a lower alkyl group, R1 is the same or different halogen atom, nitro group or trifluoromethyl group, and n is not an integer of 0.1.2. However, R
6 cannot be a single chloro position at the 4-position of the benzene nucleus. ) A benzoyl urea derivative represented by (21 compounds, N-(2,6-cyfluorobenzoyl)-N'-[4-(3,5-dichloroanilino)phenyl]urea, N-(2-chlorobenzoyl)-
4-(2,4-dichloroanilino)-3-trifluoromethylphenyl]urea, N-(2,6-difluorobenzoyl)-r-(4-anilino-5,5-dichlorophanyl)urea, N- (2-chlorobenzoyl)-N'
-(4-"7nilino6□5-dichlorophenyl)urea or N-(2,6-difluorobenzoyl)-N'-
1: The benzoylurea derivative according to claim 1, which is 4-(N-methyl-2,4-dichloroanilino)phenyl]urea. (In the formula, 1 (+ is a hydrogen atom or), a rogene atom, R'
is a halogen atom, R8 is a hydrogen atom, a halogen atom, or a trifluoromethyl group, R4 is a hydrogen atom or a halogen atom, ul is a hydrogen atom or a lower alkyl group, R@
represents a divalent or different atom, a nitro group or a trifluoromethyl group, and n represents an integer of 0.1.20. However, RM does not convert chloro into mono-Ia at the 4-position of the benzene nucleus. ) An insecticide characterized by containing a benzoylurea derivative as an active ingredient. lino)phenyl]urea, N-(2-chlorobenzoyl)-N'-
(,1-(2,4-dichloroanilino)-3-trifluoromethylphenyl]urea, N-(2゜6-difluorobenzoyl)-N'-14-7ni/-3,5-dichlorophenyl)urea , N-(2-chlorobenzoyl)
-N'-(4-anilino-6゜5-dichloroanilino-1/a or N-42,6-difluorobenzoyl)-N
'-[4-(N-methyl-2,4-dichloroanilino)
% H'v m+' which is phenyl]urea.