JPS58185563A - N-benzoyl-n'-phenylurea and insecticide containing the same - Google Patents

Abstract

NEW MATERIAL:An N-benzoyl-N'-phenylurea of formula I (X, Y are halogen, alkyl, alkoxy, trifluoromethyl, alkenyl, cyano, carboxy, alkoxycarbonyl; Z is halogen, trifluoromethyl; R is alkyl, acyl, alkenyl; l, m, n are 0, 1, 2). EXAMPLE:N-( 2-chlorobenzoyl )- N' -{ 3-chloro-4-[ N-( 5-trifluoromethyl-2-pyridyl)- N-pivaroylamino]phenyl}urea. USE:Insectcide: especially it is effective in combatting harmful insects. PREPARATION:The reaction of benzoyl isocyanate of formula II with an anline of formula III is conducted in a solvent such as benzene, toluene or water at 0-120 deg.C to give the compound of formula I .

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel N-benzoyl-N'-phenylurea compounds and insecticides containing them. A halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, an alkenyl group, a V ano group, a carboxy group or an alkoxycarbonyl group, and 2
is a halogen atom or a trifluoromethyl group, and a is a hydrogen atom, an alkyl group, an acyl group, or an alkenyl group.

! , m and n are 0, 1 or 3)
These are benzoyl-N'-phenylurea compounds and 411 agents containing them.

Examples of the halogen atoms represented by x, Y, and 2 in the general formula (1) include fluorine, chlorine, bromine, and iodine;
Y@ is R, and the alkyl group, alkyl moiety of an alkoxy group, alkyl moiety of an alkoxycarbonyl group, and alkyl moiety of an acyl group are methyl, ethyl, propyl, mesyl, pentyl, hexyl, pentadecyl,
Examples include alkyl groups having 1 to 20 carbon atoms such as eicosyl, and alkenyl groups represented by X, Y, and 8 include alkenyl groups having 3 to 10 carbon atoms such as vinyl, propenyl, and phthynyl. Ming's h-benzoyl-'-phenylurea-based compounds are usually composed of benzoyl isoleanate represented by general formula (1) (wherein X and j are as described above) and general formula (1) (formula Middle Y, Z,
It is produced by reacting with aniline represented by R, Peng and Kage are the above-mentioned values. This reaction is based on penguin, toluene, xylene, pyridine, 9ttt
hmm.

It is carried out in the presence of a solvent such as dimedel sulfoxide and water, the reaction temperature is 0 to 15Oc, and the reaction time is 0.1S-2.
It is 4 hours.

Further, the aniline represented by the general formula (1) is produced, for example, by the following method.

In the above reaction formulas [1] and [V], Y, Z1m and n are as described above, M is a hydrogen atom, a nitro group or an amino group, Haj is a norogen atom, and B' is an alkyl group. , an acyl group or an alkenyl group.

In addition, when the theory is 1 or 2; in the second case, it is desirable that A is a hydrogen atom or aib, and in such a case,
Further, by performing a usual nitration reaction and reduction reaction, or by performing a reduction reaction, the above general formula (厘)
of aniline can be obtained.

Examples of the alkaline substance include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and bi9dine, and examples of the solvent include dimethylsulfoxide and dimethylformamide.

Examples include aprotic polar solvents such as heximedel phosphoramide, pyridine, and water.

Next, a specific synthesis example of the metal product of the present invention will be described.

Synthesis example 1. N-(2-chlorobenzoyl)-N'-(3
-chloro-4-(N-(5-)lifluoromethyl-2-
Synthesis of S-chloro-5-
) Lifluoromesolviridine 211.2-chloro-4-
Nitroaniline 20II and potassium carbonate 241 were charged and dissolved in dimedelformamide 100. Next, the inside of the autoclave was purged with nitrogen, and the reaction was carried out at 180° C. for 24 hours. After the reaction is complete, transfer the product to a flask.

The solvent was removed under reduced pressure. Thereafter, water was added, and ordinary purification methods such as chloroform extraction, water washing, drying, and V licage column purification were performed to obtain 8-chloro-4-(5-trifluoromethyl-2- pyridylamino) nitropenein 7.71 was obtained.

■Next, the above nitrobenzene 2. ．． 51 to pyridine 10
- Piparoyl chloride 5. dissolved at room temperature to 60°C.
6- was added in 4 portions and allowed to react for 1 day. After the reaction was completed, the solvent was distilled off under reduced pressure.

Partition between water and chloride/methylene, and divide the organic layer into saturated sodium bicarbonate.
Washed once with
8.3y of 8-chloro-4-[N-(5-)lifluoromethyl-2-pyridyl)-N-piparoylamino]nitropenyne was obtained as an amorphous solid.

(3) Thereafter, 8.81 g of the pivaloylaminide (1 pen) was dissolved in 50 ag of ethanol, and subjected to medium pressure catalytic reduction (to 5% Pd-, ¥100,000) according to the quality.

84/ff for 1.28 hours to obtain 8-
Chloro-4-(N-(51lifluoronotyl-2-pyridyl)-N-pivaloylaminonidoniline 2611 was obtained.

4) Sarahito, dissolve 1.89 of the above aniline in dioxane 15-2-chlorobenzoylino L/r)0.
6& was added and reacted at room temperature for 4 hours. After the reaction is complete,
The product was dried to dryness under reduced pressure, and the residue was purified using a silica gel column, and then crystallized with methanol, with a melting point of 116-118°C.
We obtained the first h i, tl.

Synthesis Example 2 Synthesis of N-(2,6-difluorobenzoyl J-N'-(4-(8-chloro-5-triple 11th methyl-2-pyridylamino)fer l urea ill hexamethylphosphorotriamide l U 2,8-dichloro-5-trifluoromethylpyridine 7I, 4-nitroaniline 4.5# and sodium hydride 15 were dissolved in O- and reacted at 100°C for 2 hours. After completion of the reaction, goo! Pour the reaction solution into ice water in j, then 2
Extraction was carried out twice with 00-ether. 10 organic layers
After washing with 0 ml of saline, 9 ml of anhydrous sulfuric acid was added and dried.

The solvent was distilled off under reduced pressure to obtain 10.4# of 4-(8-chloro-5-trifluoromethyl-2-pyridylamino)nitrobenzene.

(2) After dissolving 18.5 # of the obtained nitrobenzene derivative 4 in 200 - of ztanol, 481 of tin octchloride and 48 - of concentrated hydrochloric acid were added, and the mixture was reacted for 8 hours under heating and reflux.
After the reaction is complete, ethanol is distilled off under reduced pressure, and the residue is
% sodium hydroxide aqueous solution was added to make it strongly alkaline. After extraction with methylene chloride, 4-(8-chloro-5-trifluoromethyl-2
-pyridylamino)aniline 4,5I was obtained.

(3) 4 g of the obtained aniline conductor was mixed with dioxane 80-
Then, 2,6-disolopenzoyl isocyanate 25% dissolved in 2,6-disolopenzoyl isocyanate was slowly added dropwise at ￥1,000, and stirring was continued for an additional 2 hours at room temperature.

The reaction solution was poured into 1110 sd of ice water. The white precipitate formed was washed with n-hexane, and the melting point was 244-246°C.
Fifty-five 1j animals were obtained.

Specific examples of compounds produced according to the general production method and specific synthesis examples described above are described below.

As shown in the test examples below, the compound of the present invention is active as an insecticide, especially as a self-effective ingredient of an insecticide. , Diptera such as the common ladyfly, Culex pipiens, Culex pipiens, etc., and L such as the cockroach.
.

It is effective against pests belonging to the order Ptera.

When using the compound of the present invention as a self-effective ingredient of an insecticide, it can be prepared in the form of an emulsion, a powder, a wettable powder, a preparation, etc. together with a pesticide adjuvant, as in the case of conventional pesticide formulations.
These preparations can be used as they are, or they can be diluted to a predetermined concentration with a sachet.

The pesticide adjuvants mentioned here include solid carriers such as talc, kaolin, bentite, diatomaceous earth, holinoitocarbon, clay, # powder, water, xylene, toluene, dimethyl sulfoxide, dimethyl formamide, acetonitrile,
Examples include liquid diluents such as alcohol, emulsifiers, dispersants, and spreading agents. Also, other pesticides, such as insecticides, acaricides, and fungicides, if necessary.

It can be mixed or used in combination with plant growth regulators, etc., and in this case may show even better effects1.For example, as insecticides, organic phosphate compounds, carbamate compounds, dithio (or thiol) carbamates, etc. compounds, organic chlorine compounds, dinitro compounds, organic sulfur or metal compounds, antibiotics, substituted diphenyl ether compounds, urea compounds, triazine compounds, benzoylurea compounds, and pyrethroid compounds. , benzoylurea compounds such as N-(2,6-difluorobenzoyl)-N'-(p-chlorophenyl)urea, and pyrethroids such as α-cyano-8-phenoxybenzyl-2-(4-chlorophenyl)isovalate. Examples include type compounds.

The insecticide of the present invention is effective in controlling various harmful insects, especially self-injurious insects, and the application is generally 1-10°0 (J l).
pprn, preferably at an active ingredient concentration of 20 to 2.000 ppm. Also, for livestock °(, = it
It is also possible to mix and feed the above active ingredients to feed to control the emergence and growth of pests, especially self-damaging insects, in their excreta. In addition, in the case of aquatic harmful insects, it is possible to control I and C by spraying a chemical solution in the above A degree range to the place of occurrence, so it is effective even if the concentration in water is within the above range.Test Example 1 Each of the active ingredient compounds Disperse the formulation in water,
t) A cabbage leaf was immersed in a chemical solution adjusted to # of OP pm for about 10 seconds, taken out and air-dried. Kona H larvae of 2nd to 8th instar were released there, and the lid was placed in a lighted incubator at 28'C.8 hours after release.
Viability was determined on the day, and the mortality rate was determined using the following jt formula, and the results shown in Table 1 were obtained.

Table 1 Test Example 2゜The same procedure as in Test Example 1 was repeated, except that the 2- to 8-year-old diamondback moth was changed to a 2- to 8-year-old Spodoptera japonica. The test was conducted in the same manner as in the case of , and the results shown in Table 2 were obtained.

Table 112 Test Example 8 IU (1411j
Approximately 25 liters of each of the chemical solutions of compound 1.5.7 and 8, adjusted to a concentration of p+1, were added to the people.
Hanging υ) Release the larva of Tekaiye force and close the lid-C'2M
'c +, + 4 released insects left in a thermostat with lighting <v l
I investigated the survival and death of larvae on n ++ ++ and found that it was effective. Preparation Example 1 (a) N- (2,6-difluorochloride) - I
ll(-chloro-5-trifluoromef-ru-2-bilyrelrmino)phenyl]urea
20 Emperor Rutbu (ol N, N-i/ Mef Rubo B
V Mu f Mid 7 N Apparatus Ra1, e→Polyoxyethylene alkyl soenyl alcohol 10 Mix and dissolve the above ingredients uniformly to form an emulsion and 1.

Formulation Example 2 (a) He-(2,6-difluoroyl) -N'
-(;s ri1)Rho4-CN-(5-trifluoromethyl~Z pyridyl)-N-piparoylaminocophenyl)urea, 5 parts by weight - Talc 95 parts by weight or more are uniformly ground and mixed. It was made into a powder.

Formulation Example 8 IIN-(2-chlorobenzoyl)-N'-(8-chloro-4-(N-(5-trifluoromethyl-2-pyridyl)-N-propionylaminocophenyl)urea 50
Parts by weight -) Fine powder silica 15 parts by weight e1 Fine powder clay 25 parts by weight Tetranaphthalene sulfonic acid soda formalin condensate
2 parts by weight - dialkyl sulfosuccinate
8 parts (by weight) of polyoxyethylene alkyl allyl ether sulfate 5 parts by weight or more were uniformly ground and mixed to prepare a wettable powder.

Patent applicant: Ishihara Sangyo Co., Ltd.

Claims (1)

[Claims] (In the formula, X and Y are halogen atoms, alkyl groups. Alcoquine groups, trifluoromethyl groups, alkenyl groups,
It is a cyano group, a carboxyl group, or an alkoxycarbonyl group, 2 is a halogen atom or a trifluoromethyl group, and R is a hydrogen atom, an alkyl group, an acyl group, or an alkenyl group. ! , m and n゛ are 0. l father is 2)
-benzoyl-d-phenylurea compound. k) General formula (wherein X and Y are a halogen atom, an alkyl group, an alkoxy group, a trifluoromethyl group, an alkenyl group, a cyano group, a carboxyne group, or an alkoxycarbonyl group, and Z
is a halogen atom or a trifluoromethyl group, R is a hydrogen atom, an alkyl group, an acyl group, or an alkenyl group, j, m and n are 0, - An insecticide characterized by containing at least one persimmon of a phenylurea compound as an active ingredient.