JPS60215658A - Benzoylurea derivative and insecticide containing same - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (R is 4-5C alkenyl). EXAMPLE:N-[4-(2-butenyloxy)-3,5-dichlorophenyl]-N'-2,6-difluorobenzoyl urea. USE:An insecticide exhibiting improved effect on cabbage armyworm and diamondback moth even in a small amount of chemical without fear for environmental pollution. PREPARATION:Benzoyl isocyanate of formula II is reacted with an aniline derivative of formula III in a solvent, e.g. toluene or chloroform, at 0-150 deg.C for 10min-5hr to give the aimed compound of formula I . The raw material benzoyl isocyanate is obtained from the corresponding aniline by the well-known method.

Description

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

The damage to crops caused by pests is enormous.

The damage caused by armyworms and diamondback moths is particularly severe.

Among them, armyworms are omnivorous pests that cause widespread damage to vegetables and field crops.

When it comes to vegetables, armyworms smell like cabbage.

Chinese cabbage, citrus orchid, radish, eggplant, and taro are most commonly affected, and among field crops, it is particularly common in cypress and soybeans.

A large amount of control #f costs are invested every year to control these pests.

On the other hand, in recent years, the emergence of pests that are resistant to existing grasses,
In addition, environmental pollution caused by commercially available weeds has become a problem, and insect pests can be effectively controlled with low doses.

There is a strong desire to develop new drugs that are free from environmental pollution concerns.

Until now, the general formula (In the formula, R8 is an alkenyl group having 2 to 3 carbon atoms.

R represents an alkenyl group having 2 to 4 carbon atoms mono- or di-substituted with a hydrogen atom, or a pronoclyl group;
2 and R3 independently represent a hydrogen atom or a chlorine atom, and R4 represents a hydrogen atom or a fluorine atom. (In the formula, R8 ke CH2=
CHCH2- group, CACH20CA- group.

CACH= CHCH2- group, C)T, =CCACH2
-ノ, 1., CU2C2CHCH, - group, C/3CH
It represents a 2CCACH2- group or a CH2CCH2- group, and R2 represents a hydrogen atom or a chlorine atom. ) is known to be an N-phenyl-N'-benzoyl urea derivative (see Publication No. 54-27538) or insecticidal activity.

Historically - Shimilin (Dim) as an insecticide
ilin) is commercially available.

As a result of intensive research to develop a compound with even stronger insecticidal power among base/diyl urea insecticides, the present inventors discovered that the compound of the present invention has an increased number of carbon atoms in the alkenyl ether σ) alknyl group. Even compared to the compounds specifically described in published publications and the commercially available drug Similin, it is possible to completely control diamondback moths and armyworms with lower dosages, and there is no concern about environmental pollution. He discovered that there was no such thing, and based on this knowledge, he completed a non-invention.

That is, 1. the present invention is based on the general formula (In the formula, R represents an alkenyl group having 4 to 5 carbon atoms.

) K, benzoyl urea derivatives represented by
We are proposing an insecticide containing this.

R in this general formula fIl is an alkenyl group having 4 to 5 carbon atoms, and may be either chain-like or branched.

Compound 9 of the Invention One representative example of the compound is shown in Table 1.

In addition, Compound 1 Ho is referred to in the following descriptions d and C.

Table 1 Compounds of the present invention can be prepared, for example, by the following method.

General formula.

[7.

Aniline is reacted with a visiting conductor represented by .

The above reaction is preferably carried out in the presence of a solvent, such as sulfur, benzene, toluene, xylene, etc. σ) Aromatic hydrocarbons, aliphatic and aromatic halogens such as dichloromethane, chloroform, tetrachloride, chlorobenzene, etc. Carbonized hydrocarbons, ethers such as ether, dioxane, and tetrahydrofuran, nitriles such as acetonitrile, acetone, methyl ethyl ketone, etc. σ) Ketone 3J, N+N-
Amides such as dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and the like can be used. Can the reaction temperature be varied within a fairly wide range?

Generally, a temperature in the 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.Also, the raw material penzoyl isocyanate can be produced from the corresponding aniline by a known method.

In addition, one Kakumei compound 14'/A has the general formula A benzamide candy conductor represented by and the general formula.

C! It can also be produced by reacting with an incyanate d core represented by .

The reaction can be carried out under conditions similar to those described above. Phenyl isocyanate FA, which is a member of the No. 9 family, can be produced from the corresponding aniline d4 isomer and phosgene by a known method.

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

Preparation of Compound 4 4.6 mmol (0.02 mol) of 4-(2-butenyloxy)-5,5-dichloroaniline was dissolved in 60 liters of toluene, and while stirring at room temperature, 2,6-dinolbenzoyl was dissolved. 50f toluene solution of isocyanate 3.7mM 0.02
When mol) is added dropwise, an exothermic reaction occurs.

After stirring for 2 hours at the same temperature, the precipitate was collected by filtration, washed with 11-hexane, and the desired product N-
[4-(2-butenyloxy)-3,5-dichlorophenyl] -N'-(2+6-difluoropenzoyl)
Z7?Urea is a white powder with a melting point of 167-169℃? (
A yield of 928 cm) was obtained.

The insecticide 1i'11 of the present invention can be prepared using only one compound of the present invention, or this [A, 5: 1 to 1 commonly used carriers, surfactants, dispersants, and adjuvants when preparing (7) for seven preparations. Mixed with etc.

Aqueous phase agent, emulsion 1 grain 7! Each glaze form 1c formulation such as il, powder, etc. is prepared. When using, dilute to appropriate thw℃
When producing insecticides in the form of these formulations for spraying or direct application, one of the benzoyl urea meter conductors
Merck, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermikeyite, slaked lime, silica sand, mL of ammonium*urea, etc. σ] group presses, xylene, alcohol, dioxane, acetone, cyclohexanone for seeds or 2 flj or more , liquid phase such as methylna-7crene, dimethylformamide, dimethyl sulfoxide, alcohol canate ester salt, alkyl other acid ester, alkyl sulfone e salt GA, polyoxyethylene glycol ether q, polyoxyethylene alkylaryl ether, polyoxy Various adjuvants such as emulsifier 11 dispersant such as ethylene sorbicun monoalkylate, lignin sulfonate, carboxymethyl cellulose, and gum arabic are appropriately blended and uniformly mixed, dissolved, or formulated, and θ
If desired, the compound of the present invention and other insecticides may also be used.

Next, the formulation of the insecticide of the present invention will be explained, and the strength and compounding ratio of the additives are not limited to these 4, but can be changed within a wide range. Needless to say. In the following formulation examples, all parts refer to M parts.

Example 1 (Aqueous phase agent) Compound fl + 20 parts, Kayinu ± 35 sounds (-, Clay 3
5 parts, White Carphone 5 parts, New Call 564 (Nippon Nyukaza ■' registered song at name) 3 parts, Sunextract P252
Mix and crush 2 parts of Yama@Kokusaku Valve (registered trademark name) to make a water phase agent.

Example 2 (emulsion) 22 parts of compound hx2+, 66 parts of dimethyl sulfoxide,
2≧-Calgen 5Tso (Takemoto Yushi ■C registered plug name) 15
The emulsion is applied evenly to the sound 3'.

Example 6 (Rill) 1 part of compound (4), 49 talc (S, 47 clay,
Mix and crush 3 parts of white carbon to make a powder. Save it for use and then sprinkle it as is.

The compounds of the present invention are the four commercially available stains and the above-mentioned
Compared to the compounds specifically described in the publication, it has an extremely strong insecticidal effect on diamondback moths and armyworms (Mvc), and is useful as an insecticide.

Examples of harmful insects that can be effectively controlled by the insect repellent of the present invention include the following.

Paddy rice pests: Nikameichii cormorant, kobunomith.

Good beetles, rice weevils Field crops Jffl: Spodoptera japonica, armyworms, diamondback moths, tsu' beetles, kumanaginuwaba Tea pests: Chakokakumonhamaki, Chabar-rki IR
(Insects: Pests: Kokakumonno magi, Peach beetle, Osmanthus japonicus; Insects: House fly horns; Next, the effects of the compounds of the present invention will be explained using test examples.

In addition, the following J) was used as a comparison drug and a commercially available mulberry field.

Iq-====s Obu Young (JP-A-54-128544
(described in the publication) Koji H-etc. JP-A No. 54-1285
44'+'i publication) ℃ hate ← 1 frost 1 case (Unexamined patent f!?
-54128544 Publication) Kigo; Reii Tosun (Described in JP-A-54-27538)…Henchmen (JP-A-54-27538)
4-27538 Publication) Commercially available drug test M Example 1 (Insecticidal power against Spodoptera trifoliata) Example 1
Dilute the aqueous phase agent of the compound of the present invention prepared according to 1 with water.
Next, add silkworm artificial feed to a thickness of about 5 cm (VcI/J), and re-immerse the feed pieces to the same number of hearts.

The filter paper was placed in a 60CC PVC cup. Several 5 6th instar larvae of Spodoptera japonica were kept in a constant temperature room at 25'C, and after 8 days, the number of dead and abnormal vehicles was examined. The test is 1
We tested 10 animals in 5 wards.

The test results are shown in Table 2.

Table 2 Trial sales example 2 ()・Insecticidal test against Sumonyotoso)2.
After one day, the aqueous phase of the compound of the present invention prepared according to Example IK was sufficiently sprayed with a water-diluted spray gun and placed in a greenhouse. Four days after spraying, fresh Yushichimushikan was tested.The test was carried out on 6 Danshun in one ward.

The results are shown in Table 3.

Table 5 Test muscle example 6 (Efficacy against diamondback moth) The aqueous phase agent of the compound of the present invention prepared according to Example 1 was diluted with water for 80 minutes, cabbage leaves were immersed in this solution, and after air-drying,
e(di) and release the 6th instar larvae there.
25℃tl) 4Li temperature f storage.

After 14 days, the number of adults was counted and the rate of inhibition of adult development was calculated. The test was conducted with 5 dogs in each ward, and 20 animals were tested.

The results of the 6 experiments are shown in Table 4.

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, r, 1'1: IyFi2 Name of the invention, benzoyl urea, +8 buttock body and eθ insects 3. tl A address
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f 0H-Co)], -J r OH yoeCH
I J and 61 correct.

(21. 6th shellfish ≠ 516' in Table 1, 9 corrections have been made.)

(3) General formula for number 1 of the 8th shellfish Canceled.

(4) The 12th negative ratio All /; I', 2 a
L40 type? Next 1III<Correction.

” (51 12th jt It qjz gv; Hata Condolence 3
The i1rth formula is as shown below.

Claims (1)

[Scope of Claims] A benzoylurea derivative represented by (wherein R represents an alkenyl group having 4 to 5 carbon atoms). (2) Derivative or N-[4-(2-butenyloxy)
3,5-dichlorophenyl)-N'-2,6-difluorobenzoyl chloride. An insecticide containing as an active ingredient a benzoyl urea derivative represented by 1+' y,v (wherein R represents a 4- to 5-number alkenyl group). (4) The derivative is N-[ 4-(2-butenyloxy'
) -5,5-dichlorophenyl) -N'-2,6-
Insecticidal composition 11° according to claim 3, which is difluorobenzoyl urea.