JPS6348256A - N-benzoyl-n'-phenylurea based compound and insecticide containing said compound - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I (X1 is H or halogen; X2 is halogen; R1 is alkyl which may be substituted by halogen; R2 is H, halogen or alkyl). EXAMPLE:N-2,6-Difluorobenzoyl)-N'-[3-chloro-4-(1,1,2,2-tetrafluoroetho xy)-5-meth oxymethylphenyl]urea. USE:An insecticide capable of exhibiting improved action particularly on agricultural insect pests, e.g. Plutella xylostella Linnaeus, Mamestra brassicae Linne, etc., sanitary insect pest, storage grain insect pests, clothes household insect pests, etc. PREPARATION:A benzol isocyanate based compound expressed by formula II is reacted with an aniline based compound expressed by formula III in a solvent, e.g. benzene, etc., at 0-120 deg.C for 0.1-24hr to afford the aimed compound expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to novel N-benzoyl-N'-phenylurea compounds and insecticides containing them.

(Disclosure of the Invention) The compound of the present invention is a novel N-benzoyl-N-phenylurea compound represented by the following general formula (1).

General formula (■): (wherein, XI is a hydrogen atom or a halogen atom, and X2
is a halogen atom, R1 is an alkyl group that may be substituted with a halogen atom, and R2 is a hydrogen atom, a halogen atom, or an alkyl group) As the alkyl group represented by R1 and R2 in the general formula (1), are methyl group, ethyl group, n-butyl group, 1so-butyl group, 5e
c-butyl group, tert-butyl group, etc., and halogen atoms represented by Xl, X2 and R2 and R
Examples of the halogen atom contained in 1 include a chlorine atom, a bromine atom, a fluorine atom, and an iodine atom.

The N-benzoyl-No-phenylurea compound of the present invention is, for example, a benzoyl isocyanate compound represented by the general formula (■): (wherein, Xl and X2 are as described above) and a general formula (■). ):
It is produced by reacting with an aniline compound represented by the formula (wherein R3 and R2 are as described above).

This reaction is carried out in the presence of a solvent such as henzene, toluene, xylene, octane, chlorobenzene, pyridine, dioxane, dimethyl sulfoxide, or ethyl acetate, and the reaction temperature is 0 to 120 °C and the reaction time is 0.1 to 24 °C. It's time.

The starting compound represented by the general formula (III) can be synthesized, for example, by the following method.

(A) (wherein, X is a chlorine atom or a bromine atom, R1 and R
2 is as described above) Among the raw material compounds represented by the general formula (III), the compound represented by the general formula: (■) (wherein R2 is as described above) is, for example, as follows. It can also be synthesized by other methods.

(B) Representative examples of aniline compounds that can be produced by the above production method (A) or CB) are listed in Table 1.

Table 1 Next, specific synthesis examples of the compounds of the present invention will be described.

Synthesis example 1. N-(2,6-difluorobenzoyl)
-N'-[Synthesis of 3-chloro-4-(1,1,2,2-tetrafluoroethoxy)-5-methoxymethylphenyltourea (compound 11kll) [I] 2-chloro-6-medoxymethyl-4- Nitrophenol2.
0g ethanol solution 30m7! 10% palladium in
0.1 g of carbon was added, and the mixture was stirred at room temperature for 2 hours under a hydrogen atmosphere.

After the reaction was completed, the reaction solution was filtered to remove the catalyst, the solvent was distilled off under reduced pressure, and then purified by silica gel column chromatography using a mixed solvent of n-hexane and ethyl acetate. 4-amino-2-chloro-6-methoxymethylphenol was obtained.

(n) 4-amino-2- obtained in the above step (1)
Add 0.7 potassium hydroxide to 10 ml of dimethylformamide solution of 1.0 g of chloro-6-medoxymethylphenol.
g was added thereto, the mixture was heated to 90 to 100°C, and tetrafluoroethylene gas was passed through the mixture for about 5 minutes while maintaining this temperature.

After the temperature of the liquid was returned to room temperature, extraction was performed with ethyl acetate and water, and the organic layer was washed with saturated brine and dried over anhydrous sulfuric acid. After drying, the solvent was distilled off under reduced pressure and purified by silica gel column chromatography using a 3:1 mixed solvent of n-hexane and ethyl acetate to obtain 0.51 g of 3-chloro-4-(1,1
, 2°2-tetrafluoroethoxy)-5-methoxymethylaniline was obtained.

(III) 3-chloro-4-(1,1,2゜2-tetrafluoroethoxy)- obtained in the above step (II)
A dioxane solution of 0.51 g of 5-methoxymethylaniline at 10 mA and a dioxane solution of 1.0 g of 2,6-cyfluoropenzoyl isocyanate (5 m7)! was added at room temperature. After stirring overnight at room temperature, extraction was performed with ethyl acetate and water, and the organic layer was washed with saturated brine and further dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and silica gel column chromatography was performed using a 1:1 mixed solvent of n-hexane and ethyl acetate, with a melting point of 136-138.
0.63 g of the target product was obtained.

Synthesis example 2. N~(2,6-difluorobenzoyl)
Synthesis of -N' -(4- (1,1,2,2-tetrafluoroethoxy)-3-methoxymethyl-5-methylphenyl]urea (compound 3) [I] 2-methoxymethyl-6-methyl -4-nitrophenol 1.6g
0.2 g of 10% palladium-carbon was added to 50 mj+ of the ethanol solution, and the mixture was stirred for 2 hours under a hydrogen atmosphere.

After the reaction was completed, the reaction solution was filtered to remove the catalyst, and the solvent was distilled off under reduced pressure.

The product was then purified by silica gel column chromatography using a 1:1 mixed solvent of methylene chloride and ethyl acetate to obtain 1.1 g of 4-amino-2-medoxymethyl-6-methylphenol.

(II) 4-amino- obtained in the above step (1)
Add 0.42 g of potassium hydroxide to 2-methoxymethyl-6-methylphenol I111 and make 90-10
Warmed to 0°C. Tetrafluoroethylene gas was passed through the reactor for 3 minutes while maintaining this temperature. After the temperature of the solution was returned to room temperature, extraction was performed with ether and water, and the organic layer was washed with saturated brine and further dried over anhydrous sodium sulfate. After drying, the solvent was distilled off under reduced pressure, and 0.31 g of 4-(
1,1,2.2-tetrafluoroethoxy)-3-methoxymethyl-5-methylaniline was obtained.

(III) 4-(1
, 1, 2. 2-tetraB-fluoroethoxy)-3-methoxymethyl-5-methylaniline 0.2.6 g in 3 mx of dioxane solution
- 2 m7 of dioxane solution of 0.5 g of cyfluoropenzoyl isocyanate! was added at room temperature. After stirring at room temperature for 16 hours, extraction was performed with ethyl acetate and water.
The organic layer was washed with saturated brine and further dried over anhydrous sodium sulfate. After drying, the solvent was distilled off under reduced pressure and purified by silica gel column chromatography using a mixed solvent of n-hexane and ethyl acetate.
0.44 g of the target product was obtained at a temperature of 1 to 123°C.

Synthesis example 3. N-(2,6-difluorobenzoyl) -
N'-(4-(1,1,2.2-tetrafluoroethoxy)-3-(2,2.

2-trifluoroethoxymethyl)phenyl]urea (
Synthesis of Compound Teeth 5) CI) A suspension of 1.6 g of 60% sodium hydride in dimethylformamide (10 mβ) was cooled on ice. , 2.
2. 2-) 5 ml of a solution of 5.0 g of refluoroethanol in dimethylformamide was added dropwise. After completion of the dropwise addition, the reaction solution was stirred for 30 minutes under water cooling and then at room temperature for 30 minutes, then cooled on ice again, and a solution of 1.88 g of 2-bromomethyl-4-nitrophenol in dimethylformamide (5 mj2) was added.
was dripped. The mixture was then stirred for 1 hour under water cooling and further stirred for 1 hour at room temperature to complete the reaction.

After the reaction was completed, the reaction solution was extracted with methylene chloride and 1N hydrochloric acid. The organic layer was then washed with water, saturated brine, and dried over anhydrous sodium sulfate. After drying, the solvent was distilled off under reduced pressure and purified by silica gel column chromatography using a 20:1 mixed solvent of methylene chloride and ethyl acetate. Fluoroethoxymethyl)-4-nitrophenol 1.95
I got g.

[Old 2-(2,2,2-) obtained in step (1) above
(lifluoroethoxymethyl)-4 to nitrophenol 3
．． 2.6 g of reduced iron was added to 30 ml of 9 g of acetic acid solution while keeping it at 90 to 100°C, stirred for 5 minutes, and then allowed to cool.
The reaction solution was filtered through Celite. The filtrate was extracted with methylene chloride and water, and the organic layer was washed with an approximately 5% aqueous solution of potassium carbonate. After further washing with saturated brine, it was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Next, purification was performed by silica gel column chromatography using a 2:3 mixed solvent of n-hexane and ethyl acetate to obtain 4-amino-2-(2,2,2-trifluoroethoxymethyl) with a melting point of 105-107°C. ) 1.12 g of phenol was obtained.

CIII) 20 ml of a dimethylformamide solution of 0.97 g of 4-amino-2-(2,2,2-trifluoroethoxymethyl)phenol obtained in step (II) above.
0.3 g of powdered potassium hydroxide was added to 1 and heated to 90°C. Tetrafluoroethylene gas was passed through the solution for 3 minutes, then cooled and extracted with methylene chloride and water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.

Next, purification was performed by silica gel column chromatography using a 2:1 mixed solvent of n-hexane and ethyl acetate to obtain an oily 4-(Ll,2,2-tetrafluoroethoxy)-3-(2,2,2 ,-)lifluoroethoxymethyl)aniline 0.13 g was obtained.

[TV] 4-(1,
1,2,2-tetrafluoroethoxy)-3-(2,2
, Ll-lifluoroethoxy-methyl)aniline 0.1
A solution of 0.25 g of 2,6-cyfluorohenzoyl isocyanate in 10 mL of dioxane solution of 3 g in dioxane 1
The mixture was stirred overnight at room temperature with 700 mβ. Next, extraction was performed with ethyl acetate and water, and the organic layer was washed with saturated brine.
Dry over anhydrous sodium sulfate.

After drying, purification was performed by silica gel column chromatography using a 2:1 mixed solvent of n-hexane and ethyl acetate to obtain 0.21 g of the desired product having a melting point of 100-102°C.

Representative specific compounds included in the present invention are listed in Table 2.

The compounds of the present invention in Table 2 show excellent activity as insecticides, particularly as active ingredients of insecticides, as shown in the test examples below. For example, diamondback moth, armyworm, armyworm, codling moth, pole worm (no Japanese name), tobacco budworm (no Japanese name), gypsy moth, Colorado potato beetle, ballweevil (no Japanese name), grasshoppers, wasp flies, scarab beetles, tamanaya moth, Agricultural pests such as the cabbage moth, sanitary pests such as cockroaches, houseflies, Culex mosquitoes,
It is also effective against grain storage pests such as the Japanese brown moth, the brown rice beetle, the brown rice beetle, and the Japanese white beetle, as well as against clothing and household pests such as the bur moth, black-and-white beetle, and termites, as well as flies that parasitize livestock. It is. It is also effective against various chemically resistant insect pests such as the house fly, which is resistant to organophosphates.

All of them are highly effective against the larvae, but when adult insects ingest the compounds of the present invention, they have the effect of rendering them unable to lay eggs, or even if they are able to lay eggs, preventing the eggs from turning into salmon.

When using this product as an active ingredient in insecticides, it can be formulated in various forms such as emulsions, powders, wettable powders, liquids, and pastes together with pesticide adjuvants, just as in the case of conventional pesticide formulations. I can do it. The blending ratio of these ingredients is usually 0.5 to 90 parts by weight of the active ingredient and 10 to 99.5 parts by weight of the pesticide auxiliary.
Parts by weight. When actually using these preparations,
It can be used as is or diluted to a predetermined concentration with a diluent such as water.

The agrochemical auxiliary agents mentioned herein include carriers, emulsifiers, suspending agents, dispersants, spreading agents, penetrants, wetting agents, thickeners, stabilizers, etc., and may be added as appropriate if necessary. Carriers are divided into solid carriers and liquid carriers, and solid carriers include starch, activated carbon, soybean flour, wheat flour, wood flour, fish meal, animal and vegetable powders such as milk powder, talc, kaolin, bentonite, calcium carbonate, zeolite, Examples include mineral powders such as diatomaceous earth, white carbon, clay, alumina, and sulfur powder. Liquid carriers include water, alcohols such as methyl alcohol and ethylene glycol, ketones such as acetone and methyl ethyl ketone, dioxane,
Ethers such as tetrahydrofuran, aliphatic hydrocarbons such as kerosene and kerosene, aromatic hydrocarbons such as xylene, trimethylbenzene, tetramethylhenzene, cyclohexane, and solvent naphtha, halogenated hydrocarbons such as chloroform and chlorobenzene, Examples include acid amides such as dimethylformamide, esters such as ethyl acetate and glycerin ester of fatty acids, nitrites such as acetonitrile, and sulfur-containing compounds such as dimethyl sulfoxide.

In addition, other agricultural chemicals such as insecticides, acaricides, nematicides, fungicides, antiviral agents, attractants, herbicides,
It can be mixed or used in combination with plant growth regulators, etc., and may exhibit even better effects in this case.

For example, as an insecticide, acaricide, or nematicide,
0-(4-Flomo-2-chlorophenyl) 0-ethyl S-'7'7' phosphorothioate, 2,2-dichlorovinyldimethyl phosphate, ethyl 3-methyl-4-(methylthio)phenyl isopropyl phosphoroamidate, 0 .0-dimethyl 0-4-nitro-
m-Tolyl phosphorothioate, 0-ethyl 0-4
-Nitrophenyl phenylphosbothioate, 0.
0-Diethyl 0-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate, 0.0-dimethyl o-(s, 5. 6-1-dichloro-2-pyridyl) phosphorothioate, 0. S-dimethyl acetyl phosphoroamide thionyi 1-1()-, (2,4
-Dichlorophenyl) 0-ethyl S-propyl Organic phosphate ester compounds such as 1-; 1-naphthyl methyl carbamate, 2-i
'Soproboxyphenyl methyl carbamate, 2-methyl-2-(methylthio)propionaldehyde O-
Methylcarbamoyloxime, 2,3-dihydro-2,
2-dimethylhenzofuran-7-ylmethylcarbamate, dimethyl N,N'-(thiobis[(methylimino)carbonyloxy]]bisethanimidothioate, S-methyl N-(methylcarbamoyloxy)thioacetimidate, N , N-dimethylcarbamoyloxyimino-2-(methylthio)acetamide, 2-
(ethylthiomethyl)phenyl methyl carbamate,
2-dimethylamino-5,6-dimethylpyridine-4-
Carbamate compounds such as yl dimethylcarbamate, S, S'-2-dimethylaminotrimethylene bis(thiocarbamate), 2,2', 1-1-dichloro-1,1-bis(4-chlorophenyl)ethanol, 4-chlorophenyl 2. 4. Organochlorine compounds such as 5-trichlorophenyl sulfo; organometallic compounds such as tricyclohexyltine hydroxide; (R3)-α-cyano-3-phenoxybenzyl (R3)-2-(4-chlorophenyl)- 3-Methylbutyrate, 3-phenoxybenzyl (IR3)
-cis,trans-3-(2,2-dichlorovinyl)-
2゜2-dimethylcyclopropanecarboxylate, (
R3)-α-cyano-3-phenoxybenzyl (IR
3)-cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate, (S)-α-cyano-3-phenoxyhensyl (IR
)-cis-3-(2,2-dibromovinyl)-2,2-
Dimethyl cyclopropane carboxylate, (R3)-
α-cyano-3-phenoxybenzyl (IR3)-cis, trans-3-(2-chloro-3,3,3-)lifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate, 4-methyl -2,3,5,6-titrafluorobenzyl-3-(2-chloro-3,3,3-)
IJ pyrethroid compounds such as fluoro-1-propen-1-yl)-2,2-dimethylcyclopropanecarboxylate; 1-(4-chlorophenyl)-:3-
(2,,6-difluorobenzoyl)urea, 1-(
3,5-dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl)-3-(2
, 6-difluorobenzoyl) urea, 17. (3,5
-dichloro-2,4-difluorophenyl)-3-<2
．． Benzoylurea compounds such as 6-difluorobenzoyl)urea; 2-tert-butylimino-3-
Isofuropyru-5-phenyl-3,4,5,,6-tetrahydro-2H-1,3,5-thiadiazin-4-one, trans-5-(4-chlorophenyl)-N-cyclohexyl-4-methyl- 2-oxodeacyridinone-3
- Compounds such as carboxamide, N-methylbis(2゜4-xylyliminomethyl)amine, N''-(4-chloro-〇-tolyl) -N,, N-dimethylformamidine; isopropyl (2E; 4E) Juvenile hormone-like compounds such as -11-methoxy-3,7,11-)dimethyl-2,4-dodecadienoate; Other compounds include dinitro compounds, organic sulfur compounds, urea compounds, etc. compounds, triazine compounds, etc.Furthermore, they can be mixed or used in combination with microbial pesticides such as BT agents, insect pathogenic virus agents, and the like.

For example, as a fungicide, S-hensyl 0.0-diisopropyl phosphorothioate, 〇-ethyl S, S
-Organophosphorous compounds such as diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate, 4. 5. 6. 7-Titrachlorophthalide, tetrachloroisophthalonitrile and other chlorine-based compounds; polymers of Manganese ethylene bis(dithiocarbamate), polymers of zinc ethylene bis(dithiocarbamate), complex compounds of zinc and maneb , Zinc Bis(dimethyldithiocarbamate), Ethylene Bis(dithiocarbamate), Zinc Propylene Bis(
dithiocarbamate-based compounds such as polymers of dithiocarbamate); 3a,4,7.7a-tetrahydro-N
-(trichloromethanesulfenyl)phthalimide, 3
a, 4,7.7a-tetrahydro~N-(1,1,2,
2-tetrachloroethanesulfenyl)phthalimide,
N-halogenothioalkyl compounds such as N-()dichloromethylsulfenyl)phthalimide; 3-(3,
5-dichlorophenyl)-N-isopropyl-2,4-
Dioxoimidazolidine-1-carboxamide, (R3
)-3-(3,5-dichlorophenyl)-5-methyl-5-vinyl-1,3-oxazolidine-2,4-ditin, N-(3,5-dichlorophenyl)-1゜2-dimethyl Dicarboximide compounds such as cyclopropane-1,2-dicarboximide; methyl 1-(butylcarbamoyl)benzimidazol-2-yl carbamate, dimethyl 4°4'-(o-phenylene)bis(3-thio Benzimidazole compounds such as allophanate; 1-(4-chlorophenoxy)-3,3
-dimethyl-1(IH-1,2,4-)lyazole-1
-yl)butanone, 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(IH-1,2,4-)lyazol-1-yl)butanone, cun-2-ol, 1-
(N-(4-chloro-2-trifluoromethylphenyl)-2-propoxyacetimidoylcoimidazole,
1- (2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylmethyl)-1H-
1,2,4-triazole, 1-(1-(2,4-dichlorophenyl)-4-propyl-1゜3-dioxolan-2-ylmethyl)-1H-1,2,4-)riazole, 1-( Azole compounds such as 2-(2,4-dichlorophenyl)pentyl]-IH1,2,4-lyazole; 2゜4'-dichloro-α-(pyrimidin-5-yl)benzhydryl alcohol, (± )-2,
Carbinol compounds such as 4'-difluoro-α-(IH-1,2'4-triazol-1-ylmethyl)benzhydryl alcohol; 3'-isopropoxy-
0-Toluanilide, α, α, α-trifluoro 3°
-Benzanilide compounds such as isopropoxy-0-toluanilide; Acylalanine compounds such as methyl N-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate; 3-chloro-N −(3
Pyridinamine compounds such as -chloro-2,6-sinitro 4-α,α,α-trifluorotolyl)-5-)lifluoromethyl-2-pyridinamine; other compounds include piperazine compounds and morpholine compounds. compounds, anthraquinone compounds, quinoxaline compounds, crotonic acid compounds, sulfenic acid compounds, urea compounds, antibiotics, and the like.

The insecticide of the present invention is effective in controlling various harmful insects, and the application is generally from 1 to 20. OOOppm, preferably 20-2. It is carried out at an active ingredient concentration of OOOppm. The concentration of these active ingredients depends on the form of the preparation and the method of application;
It can be changed as appropriate depending on the purpose, timing, location, pest outbreak situation, etc.

For example, in the case of harmful aquatic insects, the concentration range of the active ingredient in water is below the above range, since it is possible to control aquatic pests by spraying a chemical solution with the above concentration range to the place of occurrence.

The application per unit area is about 0.1 to 5,000 g, preferably 5 to 1 g of active ingredient compound per 108 g.
000g is used. However, deviations from these ranges are possible in special cases.

The various formulations containing the compounds of the present invention or their dilutions can be applied using commonly used application methods, such as spreading (e.g., spraying, spraying, misting, atomizing, water surface application, etc.), soil application (contamination), etc. , irrigation, etc.), surface application (painting, powder coating, coating, etc.), immersion of poisonous bait, etc. It is also possible to feed livestock with the above-mentioned active ingredient mixed with their feed, and use the excrement to control the growth and development of harmful insects, particularly harmful insects. Also, the so-called ultra low-volume spraying method
It can also be applied by. In this way, 100% active ingredient content is possible.

i 1 Disperse each formulation of diamondback moth active ingredient compound in water,
Cabbage leaf pieces were immersed in a chemical solution adjusted to a concentration of 0.000 ppm for about 10 seconds and air-dried. A Petri dish with a diameter of 9 cm was lined with moist filter paper, and the air-dried leaf pieces were placed on top of it. 2nd to 3rd instar diamondback moth larvae were released there, the lid was placed, and the container was left in a lighted incubator at 26°C. The survival rate was determined at the 7th molar after adulthood, and the mortality rate was determined using the following calculation formula, and the results shown in Table 3 were obtained.

Bud 12 Spodoptera vulgaris - The test was carried out in the same manner as in Test Example 1 above, except that the 2nd to 3rd instars of the cutworm was replaced by the 2nd to 3rd instars of the Spodoptera vulgaris, and the results shown in Table 4 were obtained.

Table 4 Formulation Example 1 (a) Compound 11h1
20 parts by weight (b) Sickle
72 parts by weight (c) Sodium ligninsulfonate 8 fi 1 part or more is mixed uniformly to prepare a wettable powder.

Formulation Example 2 (a) Compound Yin 2 5 parts by weight (b) Talc
95 parts by weight or more are uniformly mixed to form a powder.

Formulation example 3 (a) Compound number 3 20
Part by weight (b) N,N'-dimethylformamide
70 parts by weight (c) 10 parts by weight or more of polyoxyethylene alkyl phenyl ether are uniformly mixed and dissolved to form an emulsion.

Formulation example 4 (a) Sickleite 7
8 parts by weight (b) 2 parts by weight of β-naphthalene sulfonic acid soda formalin condensate (c) 5 parts by weight of polyoxyethylene alkyl sulfate (d) White carbon A mixture of 15 parts by weight or more of each component and a compound negative 4 in a weight ratio of 4:1 to prepare a wettable powder.

Claims (1)

[Claims] 1. General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1 is a hydrogen atom or a halogen atom,
_2 is a halogen atom, R_1 is an alkyl group that may be substituted with a halogen atom, R_2 is a hydrogen atom,
N- represented by a halogen atom or an alkyl group)
Benzoyl-N'-phenylurea compound. 2. General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1 is a hydrogen atom or a halogen atom, and
_2 is a halogen atom, R_1 is an alkyl group that may be substituted with a halogen atom, R_2 is a hydrogen atom,
N- represented by a halogen atom or an alkyl group)
An insecticide characterized by containing at least one benzoyl-N'-phenylurea compound as an active ingredient.