JPS5913755A - Novel agricultural drug 1-(alkylphenoxyaryl)- 3-benzoylurea and manufacture - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention generally relates to novel 1-(alkylphenoxyaryl)-6-benzoyl ureas and methods of making the same. In one embodiment, the present invention relates to benzoyluria 1 useful as a pesticide.

Prior to the present invention, several benzoylureas have been reported in the patent literature as having pesticide activity. For example, U.S. Patent No. &992,553 (published November 16, 197S)
and the same No. 4. OA 1.177 (published August 9, 1977) both disclose certain benzoylureido-diphenyl ethers and note that these compounds have insecticidal activity. Similarly K, U.S. Patent No. 3.748.
356 and 3.93 & 908 also disclose certain substituted benzoyl ureas and state that the urea compounds have potent insecticidal activity.
02M (Announced April 10, 1979) HaMiLN
! C(7enylamino)carbonylcopyridine carboxamides are disclosed and compositions of the amide and methods for controlling pests are claimed. In addition, descriptions regarding benzoyl urea are found in U.S. Patent No. 416 to 124, U.S. Pat.
．． No. 605, No. 4,064.267, No. 4,00
No. 5,223, No. 4.123.449, No. 4.0
No. 68.002, No. 4.194.005, No. 4.
No. 275.077, No. 4174639, No. 5.9
No. 89.842, German Patent Publication No. 2.901,354
(EPO15-414); and DE &104,40
7 (EP 57-8138).

However, one object of the present invention is to provide new 1-(argylphenoxyaryl)-3-benzoyl ureas. Another object of the present invention is to emulate certain 1-(alkylphenoxyphenyl)-3-benzoylurines that exhibit excellent insecticidal activity. The main purpose of the present invention is to obtain 1-[2゜4-dimethylphenoxy-3,6-dimethyl-5-chlorophenyl]-ro-(2,6-difluorobenzo-1l)-chlorine, 1-(4-( The object of the present invention is to provide novel benzoylureas such as 2,5-dimethyl-4-chlorophenoxy)-5,6-dimethyl-5-chlorophenyl)-s-(2,6-difluoropenzoyl)urea and the like. Another object of the present invention is to provide a novel method for producing benzoyl urea.A still further object of the present invention is to provide a new method for producing benzoyl urea. Another object of the present invention is to provide a method for controlling pests by applying a novel agrochemical composition. 7) It should be easily transparent to the contractor.

First, in its broad aspect, the button that distributes the present invention is C1.
The present invention relates to a novel 1-(alkylphenoxyaryl)-6-benzoyl urea, an agrochemical composition containing the compound, and a method for producing and using the same. The benzoylurea of the present invention can be represented by the following formula (1).

Here, X and Xl are hydrogen, halogen, C7-C4 alkyl, haloalkyl, polyhaloalkyl, alkoxy, polyhaloalkoxy, Y is oxygen or yellow, and m and n are 0-4. Yes, R+ represents hydrogen, hao)y'n, C1-C, alkyl, haloalkyl, polyhaloalkyl, alkoxy, R2 is water Fl, halogen, C3-C4 alkyl, polyhaloalkyl, polyhaloalkoxy, C8-C8 Alkylsulfonyl, C1-C8 alkoxy, C, -C, alkylthio, C7-C, dialkylamino, CN%
NO2, COt R4, C0NHR4(R4'''C
3-C, alkyl), and R3 represents C7-Cat alkyl; however, when n is less than 2, m cannot be from 0 to 1.The present invention will be described in detail below.

As mentioned above, the present invention relates to a novel 1-(alkylphenoxyaryl)-5-benzoyl compound, an agrochemical composition containing the compound, and a method for producing and using the same.

Therefore, suitable benzoyl ureas that fall within the range of general formula 1 described above have the following formulas 2 to 4.

0Y (4) (where x, x', Y, R,, Rt, R8, n and m are as shown above).

Particularly preferred benzoylureas are O having the following formulas 5 to 8. X OY R RIR+ Rs (7) 'R+'R+R.

(where x, x', Y-R1, R4 and R5 are as shown above).

Examples of benzoyluran compounds produced by carrying out the present invention are as follows.

1-[4-(2-methyl-3,4-dichlorophenoxy)-! +,6-dimethyl-5-chlorophenyl]-3-
(2,S-chloroolbenzoyl)urea, 1-[4-(2-methyl-44-dichlorophenoxy)
-5,6-dimethyl-5-chlorophenyl]-3-(
2-chlorobenzoyl)urea, 1-(4-(2-methylphenoxy)-46-dimethyl-5-chlorophenyl)-3-(2,6-chloroorpenzoyl)urea, 1-(4-(2-methyl) phenoxy)
-,,6-dimethyl-5-chlorophenyl)-3-(2
,6-dichlorobenzoyl)urea, 1-(4-(2-methylphenoxy)-s,s-dimethyl-5-chlorophenyl]-3-(2-chlorobenzoyl)11.1-[:
4-(2-methylphenoxy)-3,6-cymethyl-5
-chlorophenyl]-3-(2-chlorobenzoyl)thiourea, 1-(4-(2-methylphenoxy)-3,6
-Simethyl-5-chlorophenyl)-3-(2-methylpensoyl)thiourea, f-(:4-(2-methylphenoxy)-2,3,5,/i-tetramethylphenyl)
-s-<2.6-dimethylpensoyl)F4. elemental, 1-
(4-(2-methylalynoxy)-2,15,6-tetramethylphenyl)-3-(2,6-methylbenzoyl)thiourea, 1-[4-(2-methylphenoxy)-2
,3,5,6-tetramethylphenyl]-5-(2,6
-) fluorobenzoyl) urine 1.1-[4-(2-methylphenoxy) -2,3,5,6-tetramethylphenyl']-3-(2,6-dichlorobenzoyl) urine!
.

1-(4-(2-methylphenoxy)-2,A5-trimethylphenyl)-3-(2,6-dichlorobenzoyl)urea, 1-(4-(2-methylphenoxy)-, 5
-dichlorophenyl]-3-(2,6-chlorobenzoyl)urine 1゜1-[4-(2-methyl-4-bromphenoxy)-3,s-dimethyl-5-chlorophenyl]
-3-(2,6-chloroolbensoyl)urea, 1-(4-(2-methyl-4-bromphenoxy)-6-dimethyl-5-chlorophenyl]-3-(2-Jlorbensoyl)urea , 1-(4-(2-methyl-4-bromphenoxy)-3
,6-dimethyl-5-chlorophenyl)-g-(2-chlorobenzoyl)thiourea, 1-(4-(2-methyl-4-bromphenoxy)-3
,6-dimethyl-5-chlorophenyl)-3-(2-methylbenzoyl)thiourea, 1-(4-(2-methyl-4-bromphenoxy)-2
, ro, 5.6-tetramethylphenyl]-3-(2,6
-')fluorobenzoyl)urea, 1-[4-(2-methyl-4-bromphenoxy)-2
,3,5-tetramethylphenyl”J-3-(2,6-
Chlorobenzoyl)urea, 1-[4-(2-methyl-4-bromphenoxy)-3
,5-dimethylphenyl)-x-(2,s-chloroolbenzoyl) Urine L1-(4-(2-methyl-4-bromphenoxy)-3,5-dichlorophenyl)-3-(
2-chlorobenzoyl)urea, 1-[4-(2-bromo-4-methylphenoxy)-3,6-dimethyl-5-chlorophenyl, :l-3-(2,S-difluorobenzoyhel)urea , 1-(4-(2-bromo-4-methylphenoxy)-s
, s-dimethyl-5-chlorophenyl]-3-(2-chlorobenzoyl)urea, 14'4-(2-bromo-4-methylphenoxy)-2
,3,5,S-tetramethylphenyl]-3-(2-chloro/soil) 151i, 1-[4-(2-bromo-
4-methylphenoxy)i,5-dichloro7xnyl]-
3-(2,S-chloroolbenzoyl)urea, 1-[4
-(2-bromo-4-methylphenoxy)-3,s-dimethylphenyl]-3-(2-methylbenzoyl)thiourets, 1-(4-(2-methyl-4-t-butylphenoxy)- 1,s-dimethyl-5-chlorophenyl]-x
, -(+,s-cyfluorobenzoyl)urine1. 1-[4-(2-methyl-4-t-butylphenoxy)
-3,/)-dimethyl-5-chlorophenyl]-3-(
2-chlorobenzoyl)urea, 1-[4-(2-methyl-4-t-butylphenoxy)
-2,45,6-tetramethylphenyl]-3-(2,
s-chloroolbenzoyl) urine1. 1-(4-(2-methyl-4-t-butylphenoxy)
, 5,5-dichlorophenyl)-3-(2-methylbenzoyl)thiourea, 1-[4-(2-methyl-4-chlorophenoxy)-3,6-dimethyl-5-chlorophenyl]-3- (2,5-chloroolbensoyl)urea.

1-[4,=(2-Methyl-4-chlorophenoxy)-3,5-dichlorophenyl]-3-(2-methylbenzoyl)thiouric acid,? -[4-(2-Methyl-4-chlorophenoxy)-2,3,5,"6-tetramethylphenyl]-3-(2,S-chlorobenzoyl)urea.

1-(4-(2-methyl-4-chlorophenoxy)-s
, 6-dimethyl-5-chlorophenyl]-5-(2,6
-')methoxypenzoyl)urea, 1-(4-(4-nonylphenoxy)-3,6-dimethyl-5-chlorophenyl]-3-(2,6-difluoropenzoyl)urea, 1-(4- (4-nonylphenoxy)-2,xs,s-tetramethylphenyl)-1-(2
-chlorobenzoyl)thiourea, 1-[4-(4-nonylphenoxy)-3,5-dichlorophenyl]-5-(
2,6-chloroolbenzoyl)urea, 1-[4-(4
-nonylphenoxy)-3,5-dimethylphenyl]-
1-(2-methylbenzoyl)urea, 1-(4-(2-
Chlor-4-methylphenoxy)-X, 6-dimethyl-5-chlorophenyl)-3-(2,S-chloroolbenzoyl)urea, 1-(4-(2-chloro-4-methylphenoxy)-3
,7S-dimethyl-5-chlorophenyl]-3-(2-
Chlorbenzoyl) thiourea.

? -(4-(2-chloro-4-methylphenoxy)-5-dichlorophenyl]-5-(2,6-1 fluorobenzoyl)urea, 1-C4-(2-chloro-4-methylphenoxy) )-2,3,s,6-tetramethylphenyl]-3-(2,6-chlorobenzoyl)urea, 1-[4-(3,4,5-trimethylphenoxy)-3
,6-dimethyl-5-chlorophenyl)-3-(2,S
-difluoropenzoyl)urea, 1-(4-(a4.s-trimethylphenoxy)-s,
s-dimethyl-5-chlorophenyl)-3-(2-chlorobenzoyl)thiourea, 1-(4-(3,4,5-trimethylphenoxy)-2
, s, s, 6-tetramethylphenyl)-3-(2-methylbenzoyl)thiourea, 1-[4-(3,4,5-
trimethylphenoxy)-3,5-dichlorophenyl]
-5-(2,6-')fluorobenzoyl)urea, j-
[4-(2,3,5-)dimethylphenoxy)-3,6
-Simethyl-5-chlorophenyl]-! 1-(2,6-
cymethoxybenzoyl)urea, 1-[4-(2,3,5-)dimethylphenoxy)-2
,3,5,6-tetramethylphenyl, :l-3-(2
,6-chloroolpensoyl)urine%,1-(a-(2,
3,5-)dimethylphenoxy)-3-iso-propylphenyl)-5-(2-methylbenzoyl)thiourea, 1-[4-(2,&5-)dimethylphenoxy)-3
-) fluoromethylphenyl) -S- (Z, 6-chlorobenzoyl) Yanzi, 1-[4-(2-methyl-4
-trifluoromethylphenoxy)-36-dimethyl-5-chlorophenyl]-1-(2,6-chloroorbenzoyl)urea.

1-[4-(2-methyl-4-trifluoromethylphenoxy)=5.6-dimethyl-5-chlorophenyl']
-3-(2-chlorobenzoyl)thiourea, 1-(4-(2-methyl-4-)!J chlorulmethylphenoxy)-3,5-dichlorophenyl 14-(2,
6-Simethoxybenzoyl) Urine 1. 1-(4-(2-methyl-4-trifluoromethylphenoxy)-2,3,5-)dimethylphenyl]-3-(
2-methylbenzoyl)thiourea, j-[4-(2,4-dimethy/I/phenoxy) -2
,3,6-)dimethylphenyl]-5-(2-chlorobenzoyl)urea, 1-(4-(5,5-dimethylphenoxy)-2,6-dimethylphenyl)-5-(2,s-
chlorobenzoyl)urea, 1-[4-(2-methyl-4-methoxyphenoxy)-6-dimether-5-chlorophenyl]-3-(2,6-difluoropenzoyl)urea, 1-[4- (2-Methyl-4-dimethylaminophenoxy)-3,6-dimethyl-5-chlorophenyl")-3
-(2,6-)fluorobenzoyl)urea, 1-[4-(2-methyl-4-methylthiophenoxy)
-3,15-dimethyl-5-chlorophenyl]-3-(
2,6-difluoropenzoyl), 1-[4-(2-methyl-4-methylsulfonylphenoxy)-he6-dimethyl-5-chlorophenyl]-3-
(2,6-chloroolbenzoyl)chloride, 1-[4-(2-methyl-4-dimethylaminophenoxy)-3,5-dimethylphenyl]-3-(2-methylbenzoyl)urea, 1-[ 4-(2-methyl-4-methoxyphenoxy)-3-chloro-6-methylphenyl]
-3-(2-methylbenzoyl)Seki Lj-[4-(2-
methyl-4-methoxyphenoxy) to 3,6-dimethyl-5-chlorophenyl)-3-(3,4-dichlorobenzoyl)urea, 1-[4-(2,3-dimethyl-4-bromphenoxy)- 3,6-dimethyl-5-chlorophenyl)-3-(
2-chlorobenzoyl)urea, 1-1:4-(2,5-dimethyl-4-chlorophenoxy)-3,6-dimethyl-5-chlorophenyl]-3-
(2,6-difluoropenzoyl)urea, 1-(4-(2,5-dimethylphenoxy)-6 rhodimethyl-5=chlorophenyl)-3-(2,6-difluoropenzoyl)urea.

1-(4-(2,5-dimethylphenoxy)-3,S-
dimethyl-5-chlorophenyl)-3-(2-chlorobenzoyl) element, 1-L:4-(2,5-dimethyl-4
-ethoxycarbonylphenoxy)-3,6-dimethyl-5-chlorophenyl)-3-(2,6-difluorobenzoyl)urea, 1-[4-(2,5-dimethyl-4-ethoxycarbonylphenoxy)-3 ,6-dimethyl-5-chlorophenyl]-3-(2-chlorobenzoyl)urea, 1-[:4-(2-methyl-4-trifluoromethylphenoxy)-, ,6-dimethyl-5-chlorophenyl]
-3-(2-chlorobenzoyl)urea, 1-(4-(2,5-dimethyl-4-trifluoromethylphenoxy)-3,6-dimethyl-5-chlorophenyl:)-3-(2,6- difluoropenzoyl)urea, 1-(4-(2,s-dimethyl-4-trifluoromethylphenoxy)-3,6-dimethyl-5-chlorophenyl)-3-(2-chlorobenzoyl)urea, 1-( 4-(2,5-dimethyl-4-trifluoromethoxyphenoxy)-1,S-dimethyl-5-chlorophenyl)-3-(2゜6-difluorobenzoyl)urea, 1-[4-(2, s-dimethyl-4-trifluoromethoxyphenoxy)-3,6-dimethyl-5-chlorophenyl]-3-(2-chlorobenzoyl)urea, 1-(:4-(2,5-dimethyl-4-methoxyphenoxy) )-46-dimethyl-5-chlorophenyl)-3-
(2,6-difluorobenzoyl→urea, 1-[4-, (2,5-dimethyl-4-methoxyphenoxy)-3,6-dimethyl-5-chlorophenyl)-3
-(2-chlorohendiyl)urea, 1-[4-(3,5-dimethyl-4-chlorophenoxy)-1,6-dimethyl-5-chlorophenyl]-3-(
2,(S-difluorobenzoyl)urea, 1-('4-(2,4,5-)dimethylphenoxy)-
s,s-dimethyl-5-chlorophenyl)-3-(2,
S-difluorobensoyl) 1-[4-(2,4,5-)dimethylphenoxy)-3
,6-dimethyl-5-chlorophenyl)-3-(2-chlorobenzoyl)urea, 1-1:4-(2,5-dimethyl-4-bromphenoxy)-6-dimethyl-5-chlorophenyl]- 3-(
2,6-difluoropenzoyl)urea, 1-[4-(2,5-dimethyl-4-cyanophenoxy)-3,6-dimethyl-5-chlorophenyl]-6-(
2,6-difluorobenzoyl)urea, 1-(4-(2,5-dimethyl-4-cyanophenoxy)-s,6-dimethyl-5-chlorophenyl]-3-(
2-chlorobenzoyl)urea, 1-(4-(2-methyl-4-cyanophenoxy)-1
,6-dimethyl-5-chlorophenyl)-3-(2,6
-difluoropenzoyl)urea, 1-(4-(2-methyl-4-cyanophenoxy)-4
6-dimethyl-5-chlorophenyl)-3-(2-chlorobenzoyl)urea, 1-[4-(2,4-dimethylphenoxy)1,6-dimethyl-5-chlorophenyl)-3-(2,6- difluorobenzoyl)urea, 1-(4-(2,4-dimethylphenoxy)-46-dimethyl-5-chlorophenyl]-X-(2-chlorobenzoyl)urea, 1-[4-(2,5-dichloro) -4-methylphenoxy)-3,s-dimethyl-5-chlorophenyl]-3-(2,6-difluorobenzoyl)urea, l-14-(2,5-dichloro-4-methylphenoxy)-3 ,6-dimethyl-5-chlorophenyl"J-5-
(2-chlorobenzoyl), 1-(14-(2-methyl-4,5-dichlorophenoxy)-16--dimethyl-5-chlorophenyl]-3-
(2,s-difluoropenzoyl)urea, 1-[:4-(2-methyl-4,5-dichlorophenoxy)-1-dimethyl-5-chlorophenyl]-3-(2
-chlorobensoyl)urea, 1-(4-(2,5-dimethyl-4-chlorophenoxy)-5-methylphenyl]-5-(2,6-difluorobensoyl)urea, etc.

These novel benzoylureas of the present invention can be conveniently determined by one or more methods. for example,
The compound of the present invention can be produced according to reaction formula T by reacting alkylphenoxyaniline (9) with benzoyl isocyanate or penzoyl isothiocyane H11.

Reaction formula ■ (11(91 x + (Rt) ” (1) [Here, X, X', Y, Rt, Rt,
Rs, m and n have the meanings already stated with respect to formula (1)].

Alternatively, the novel compounds can be prepared by reaction with alkyl phenoxyphenyl isocyanates) tJ3 t<nzoamides 01) according to Scheme II.

Reaction formula ■ 01) 02) (1) [Here x, x), Y, Rt, Rt, R,,
m and n have the meanings already described with respect to formula (1)].

Generally, the reactions exemplified in Reaction Formulas (1) and (2) can be carried out in an organic solvent such as an aromatic hydrocarbon, a halogenated hydrocarbon, or the like. Solvents such as toluene and 1,2-dichloroethane are preferred. The kneading reaction proceeds at temperatures ranging from room temperature to 150°C.

The intermediates shown in Schemes I and H can be prepared according to generally accepted procedures. or substituted benzoyl isocyanate (101) according to the general procedure of 5peziale (J, Org, Chem, 27.3742
(1962): can be prepared from the corresponding benzamides according to IK.

Substituted isothiocyan and benzoyl f11 can also be produced from the corresponding acid chloride and potassium thiocyanate.

This procedure is similar to the method used by Ambelang et al.
mer, C:hem, Soc, , 61.632
(1937)) similar to K.

Aniline (9) can be produced according to the following reaction formula ([example]).

(+ 3) rl 41
1+51(9) (where Rt, Rt, Rs, m and n have the same meaning as shown in formula 1).

Substituted chlornitrobenzene 0 Substituted phenol (14
) The reaction with nitroether 051, which had a substituted nitroether, proceeded in the presence of a certain filler in a wet state, and the reduction of the nitroether 051 to aniline (9) was carried out using a heterogeneous hydrogenation catalyst in a hydrogen atmosphere. more achievable. Appropriate MI: K,
Includes palladium or platinum or runny nickel on charcoal. Temperatures ranging from 20 to 100 psi at ambient temperature may be applied. Suitable solvents include aromatic hydrocarbons or alcohols. Also, nitroether f+51, aniline 1. ! '+1 to no' Jf! , Genha, F;.

Intermediates such as 14-substituted chloronitrobenzene and 8m phenol, which can also be achieved by chemical methods using the procedure of Enders et al. It can also be manufactured by

The specific chlornitrobenzene C16) is produced roughly according to the reaction formula (2) shown below.

Reaction formula ■ 161 Aniline (9) is converted to incyanate or isothiocyanate UK by reaction with phosgene or thiopo, spray as shown in the following formula: +9+
03 (here Y, R,,R
, , R3, m and n have the meanings shown in Formula 1).

Compounds contemplated by the present invention can be used as insecticides according to methods known to those skilled in the art. Non-drug compositions containing the active or toxic compound usually include a phase and/or diluent (liquid or solid).

Suitable liquid diluents or carriers include water, petroleum distillates or other liquid substances with or without surfactants. Liquid concentrates include one or more of the compounds in acetone, xylene, or nitrobenzene.

They can be prepared by dissolving them in non-phytotoxic solvents such as cyclohexanone or dimethylformamide, or by dispersing the compound (the poison) in water with the aid of suitable surface-active emulsifiers or dispersants.

The selection of the emulsifier or dispersant and the amount used depends on the nature of the composition and the ability of the nucleating agent to promote the dispersion of the poison. In general, it is desirable to use an agent that is as fresh as possible so that it will not be re-emulsified by rain and washed away from the plant after application to the plant, and that is compatible with the intended poison dispersion in spray form. Nonionic, anionic or cationic dispersants or emulsifiers can be used. Examples include alkylarylsul*ne), 8-mer ether alcohols, quaternary ammonium compounds, organic acids, condensates of phenol and alkylene oxide, and the like.

When producing wettable powder, dust or granular compositions,
The active ingredient is dispersed in or on a suitably ground solid carrier such as clay, talc, bentonite, diatomaceous earth, Fuller's top, and the like.

In addition to the dispersant, a lignosulfonate is included in the wettable powder formulation.

The required amount of toxic agent contemplated by the present invention is 1 to 200 gallons or more of liquid carrier and/or diluent or about 5 to 500 tb of inert solid phase and/or diluent per kneeker to be treated. used. Concentrations in liquid formulations typically range from about 10 to 951%, and concentrations in solid formulations range from about 0.5 to 90% by weight. A suitable spray, dust or granulate for general use contains about 3 A to 15 bonds of active material per knee car.

The pesticide contemplated by the present invention can be applied to plants or other substances to prevent insects from attacking the plants or other substances, and can also have relatively high residue levels. Shows digit character. Regarding plants, the pesticide has a high margin of safety as it does not decompose or damage plants even when used in amounts sufficient to kill or repel R5 insects. The pesticide may also be washed away by rain, exposed to ultraviolet light, oxidized, or hydrolyzed in the presence of moisture, or at least significantly reduce the desirable pesticide properties of the plant or impart undesirable properties to the poison, such as phytotoxicity. Resists weathering, including decomposition, oxidation and hydrolysis. Furthermore, because the toxin is chemically very inert, it is compatible with virtually any other ingredient in the spray formulation and can be applied to the seeds or roots of soil plants without damaging them. It can be used on top of soil or in soil. If desired, mixtures of the active compounds of the invention or of the active compounds and other biologically active compounds or ingredients can be used.

The following examples illustrate the best mode currently contemplated for carrying out the invention.

Example 1 Under pressure nitrogen in a flask with R&L and a stirrer"'Q,
5.6-') methyl-4,5-dichloronitrobenzene (say, [L23 mol), 2,4-dimethylphenol (58,5,?, 0.32 mol), potassium carbonate (say, o, g6 mol) and dimethylformamide (125-). The mixture to be produced is 90 to 10
Heated at 0°C for 72 hours. The mixture is then cooled,
Filter and concentrate to give a dark oil. Add this to toluene (
300π/) and 4% sodium hydroxide (250d) and the layers were separated. The organic layer was washed with water and brine, dried (Na2SO4) and concentrated to a dark oil. This oil was triturated with hexane and a solid formed. This solid was cleaned with cold hexane and dried under reduced pressure to produce a tan powder (47,89,01
mp78~80'' Analysis: C+*
HIA CI NOs value: C62,85,H
527, H4, 58 actual measurements: C6547, H535
, N, H49 Example 2 4-(2,4-dimethylphenoxy)-3,6-dimethyl-5-chloronitrobenzene (259, stsm
Carbon (t o
g) Added the top 5 grams of platinum. 20 p of the resulting mixture
si was subjected to hydrogenation. After 4.5 hours, the reaction mixture was filtered through Celite and concentrated to give an oil (24,51). This turned into a pale pink solid after drying under high vacuum. m
p86-88℃0 analysis: C101Ls C
I NO theoretical value: C69,69, H653, N50
8 fruit flill Sen: 07G, 02, H&60, N5
68 Ordinance 4-(5-methyl-4-methylthiophenoxy)-5
,6-dimethyl-5-chloronitrobenzene (5,og
, 1 tsmM) in p-dioxane (7.5 ml) was dissolved in SnClt・2L O (10,09,44,4 m
M) and concentrated HCI (1 [15 m/) were added. The resulting mixture was heated to reflux for 65 minutes, cooled and treated with Na
OH (20 g), L O (50 ml) and ice (s
Pour into the mixture. This was extracted twice with toluene. - Combined organic extracts in 4% NaOH, L O
and washed with brine.

It was then dried (Nl'tSOa) and concentrated to give a yellow oil. The oil was cooled and triturated with cold hexane and traces of ethyl acetate to form a solid. This solid was filtered and washed with hexane to produce a light (beige) powder (3,06,
9,9,9mM) was obtained. m980-86℃ (decomposition) Analysis: C+n H,s CI NO3 theoretical value:
C6234, H5,89, H4,55 Actual value: C6
2,3B, )(5,8?, N425 Example 3 4-(2,4-dimethylphenoxy)-6-dimethyl-5-chloroaniline (4,94g, 179mM) in toluene (12,5m/) temperature Add isocyanate 2- to the solution.
Toluene (t5+) of chlorbenzoyl (4.21g)
r+/) solution was added. The resulting mixture was heated at 90°
heated for an hour. Then cool and add hexane 5mtY::
Diluted. The mixture was filtered and the solid was dissolved in toluene at 50%
% hexane.

After drying under reduced pressure at 80° overnight, a white solid (&321.
15.8mM). m9163-165℃.

Analysis: Cs Htt CIt Nt O
s Theoretical value: C6506, H4,85, N & 12 Observed value: C6553,) I4.94, N2O2 in a similar manner as used in the preceding example and using one of the previously disclosed reaction schemes. , produced other urea compounds. What is the f substituent in the general formula and analytical data? Published in ``K''AI: Representative identified examples of new compounds were measured and evaluated for their pesticide activity against insects, including butterfly and moth larvae and beetles. The novel compounds were tested for persimmonity in important crops including cotton.Furthermore, the novel compounds were evaluated for mammalian toxicity.

Emulsify 1 g (10 g of the weight of the test compound) of the alkylphenoxypolyethoxyethanol surfactant in pre-dissolved acetone 5D as a dispersant to test compound II! A suspension of the test compound was prepared by dissolving the solution. The solution formed was diluted with 150+++/KrN water to give about 200 ml of a suspension containing the compound in finely divided form. The compound content of the raw material suspension thus prepared was 0.5% by weight. Weight pp used in the following test
The rr1% degree was obtained by appropriately diluting the above raw material suspension with water.

The test method is as follows: Larvae of Southern United States 7-1 tow [5podoptera eridania] reared on legume tender greens at a temperature of 80±5 degrees and a relative humidity of 50±5 degrees.

(Cram, )) was used as the test insect.

The raw material suspension was diluted with water to give 50 ml per final formulation signal part.
Test compounds were formulated by forming a suspension containing 0 parts of test compound. Place the standard grade Tengu Green, a legume in the cherry blossom season, cultivated with bees on a rotating disk. Dew Bilbis (1
) evilbiss ) The above test compound formulations 1DO to 110- were sprayed by use of a spray gun. Continued spraying for 25 seconds was sufficient to wet the plants to the point of dripping. As a control, plants similarly infested with larvae were sprayed with a 100 to 110 water-acetone emulsifier solution containing no test compound. When this was dry, the leaves in pairs were separated and each was placed in a 9-way vitriol dish lined with moistened F paper. In each dish, five randomly selected larvae were placed. introduced,
Cap, label and identify and hold below 80-85 for 3 days.

The larvae could easily consume the entire leaf within 24 hours, but did not feed the upper filler. Larvae that cannot move their body length even when stimulated by prodding are considered dead.
-0 Mortality at each concentration level was recorded.

Legume t at a temperature of 80 ± 5 and relative immersion of 50 ± 5
Fourth-instar larvae of insects of the genus Epilacidae (Epilac) reared on lq.
hna varivestis, Mllll! l,
) were used as test insects.

The raw material suspension is diluted with water to give a concentration of 50% per million parts of final formulation.
Test compounds were formulated by forming a suspension containing 0 parts of test compound. 100% of the test compound formulation described above was prepared by placing standard-grade, standard-season legume tender greens grown in bees on a rotary plate and using a Dew Bilbis spray gun with air pressure set at 40 psig.
~110- was sprayed. Spraying for 25 seconds was sufficient to wet the plants enough for the solution to run off. As a control, plants similarly infested with larvae were treated with a water-acetone-emulsifier solution containing no test compound.
110m/! It erupted. When the dough was dry, the paired leaves were placed in separate Petri dishes lined with moistened P paper. Five larvae were introduced, strained, labeled, and kept under 80±5 for 6 days.The larvae could easily consume the entire leaf within 24-48 hours, but No food was available. Larvae that could not move their body length even when stimulated were considered dead.

Commercially obtained and temperature 80±5 below, relative humidity 50±
Tano; small moth (weight approx. 4.5
1117 ) (He1iothis viresce
ns, l'i', ) and the larvae of O. eliothis (weighing approximately 2.5 ■) [1 ■ eliothis zea,
(13oddie) :) was used as the test insect.

Treated and dried cotton leaves were introduced into a 9-vetri dish following a similar procedure as above, except that M plants were used instead of legumes. The test was organized into batches of 10 Petri dishes. One randomly selected larva was introduced into each set of 10 plates, and the plates were covered. They were labeled and identified and held below 80±5 for 5 days.

The biological properties of specific examples representative of the compounds of the present invention are listed in Table ■ below: Table [I I A
A2 A
A3 A
A4 A
A5 A
A6 A
A7 A
A8
A A9
A A10
A A11
A Ai2
A A13
A A14
A A15
A A16
A A17
A A1
8 A
A19 A
A20 A
A21 A
A22 A
A23 A
AC=No control ■(H) Example sAw(”MBB(
2'(lj Southern United States fall armyworm table■ (continued) 50 A
A53
A A54
A A55
A A
56 A
A57 A
A58
A A59
A A6
0 A
A61 A
A62
A A63
A A (54
A A 66 A
A67C
A68 CA69
A
A70A
A71
CA72 CA7
3 CA74
A A7
5 A
A76 A
A77
A A78
A A79
A
Table A (continued) Activity 500ppm Example 5AW(1) MBB(
2) 80A
A81 A
A82
A A8! l
A A84
A A85
A
AB6 A
A87 A
A88
A A89
A A90
CA91
A A92
CA93
A A94
A A96
A A97
A
C98A A 99 A
A101 B B A A lO3A A (1) Armyworm in the southern part of the United States (2) Insects of the genus Spotted beetle of the family Chimrididae (3)
Code 2 A = Complete control B = Moderate control C = No control ■ (continued) 104 A
A109 A
AC = No control ■ (Continued) Example s Aw<” M B
B (2) B; Moderate control C = No control ■ (continued) Activity 500 ppm Example 5AW (1) MBB (
2) 155 A
A156
A A157
A A158
A
A159 A
A16OA A 161 A
A152
A A166
A A164
A A1
65 A
A166
A A167
A
A168 A
A169
A A170
A
A172 A
A174
A A175
A A17
SCA177
A
A178 A
A179
A AlBOA
C 181A A 182A
A183
AA Examples 212-217 Representative benzoylureas were compared to known compounds to demonstrate enhanced biological activity against armyworm in the southern United States. The results are listed in the following table ■: F t.

Typical benzoyl urea JE against southern fall armyworm
, - Comparison with conventional compounds that are closely related to Kanren U - "------
-Compound pplTl former, Ugly 1-(4-(2,4-dimethylphenoxy)-3-
125 1001-(4-(2,4-dimethylphenoxy)-3,6-21001-[:4-(2,
4-dimethylphenoxy)-&6-2
100 dimethyl-5-chlorophenyl)-3-(2-
Chloro 1 90lupenzoyl) thiourea (
Example ◆16) 1-(4-(2,4-dimethylphenoxy)-3,5-
8100 dimethylphenyl)-3-(2,6-difluoropene 2 100 zoyl) urea (Example + 4) (3) Conventional compound, German Patent Publication DE 3,104,
407 (EP 57-888) Examples 218-220 Heliothis K: Representative benzoylureas were compared with known compounds to establish their enhanced biological activity against Heliothis K. The results are summarized in Table ■ and Table V below: Table ■ Notes (1) Known compound, Dimilin ■ (2)
Conventional compound, German patent publication 2,901.334 (3)
Conventional compound, German patent publication DE3.10/1,407
(EP57-888) Table ■ ]ens 1-(4-(2,5-dimethyl-4-chlor
α63phenoxy)i,6-dimethyl-5-chlorophenyl)-3-(,2,6-difluorobenzoyl)
Urea (example≠145) 1-1:4-(2-methyl-4-t-butyl
2.4Phenoxy)-3,6-dimethyl-5-chlorediyl)urea (Example 57) Notes (1) Known compound, Dimilin.

(2) Conventional compound, German Patent Publication No. 2,901.35
4(3) Conventional compound, German patent publication DE3,104
, 407 (Ep 57-888) Although the invention has been illustrated by the above examples, it is not intended to limit the invention to the materials used in these examples.

On the other hand, it should be understood that various modifications/changes may be made without departing from the spirit and scope of the invention as set forth in the appended claims.

1.7. ：＋－４・ Name of the agent Motohiro Aiuchi 1. Procedural amendment 9 (August 10, 1980, Indication of the case of Kazuo Wakasugi, Commissioner of the Patent Office, Patent Application No. 116286 of 1988) Relationship with the case of the person making the amendment Name of the patent originator Union Carbide Corporation Agent 103 Address Oil and Fat Industry Hall, 3-13-11 Nihonbashi, Chuo-ku, Tokyo Phone: 273-6436, -1 Uramasa Object of 1st generation Italy→Korokureiwa - Invention of specification @ -,': 工""','-,＋・
Contents of the Detailed Description of the Invention Column Ura Masa The amendments are made as stated in the specification submitted in the attached sheet.

t [XX
J tillct5 iter 2-6 j
2-Correct with CIJ.

Claims (1)

[Claims] 1. Formulas X and X' are hydrogen, halogen, C1-C4 alkyl, haloalkyl, hollyhaloa, alkoxy, polyhaloalkoxy, Y is oxygen or sulfur, m and n are 0- 4, RIIts water%, halogen, C1-C4 alkyl,
P4 haloalkyl, polyhaloalkyl, alkoxy ~ R2 is hydrogen, halogen, C8-C4 alkyl, polyhaloalkyl, polyhaloalkoxy, CIゝC8 alkylsulfonyl, C1-C, flukoxy, C1-C8 alkylthio, C1-C, dialkylamino, CN, NO2,
s COz R4, C0NHR4 (R4= C1~C8
alkyl), and R3 represents C1-CI! It represents alkyl, but when n is less than 2, m cannot be from 0 to 1. ] The compound according to claim 1, having the Z formula % as defined in claim 1. Five formulas Rr Rr (Rt)n (where X%X'SY, Rr, Rt, Rs s
Claim 1' with m and 11 as defined in claim 1)! l First apical compound. 4. The compound according to claim 1, wherein formula % is as defined in claim 1. 5. A compound according to claim 1 having the formula (% is as defined in claim 1) 6. Formula % is as defined in claim 1 The compound according to claim 1, which has the following. 7. A compound according to claim 1, wherein formula % is as defined in claim 1m. 8. Claim 1 741', A chemical compound having the formula % (% is the trace defined in Claim 1). 9. The compound according to Claim 1 Sakai, which is 1"-oxygen. 10. The compound according to Claim 1F, wherein Y is sulfur. 1t Y is l!, and X is hydrogen or・Rogen, Xo is ・Rogen, R1 is chlorine or methyl, R7 is ・Rogen or C8-C4 alkyl, R3 is C1-C, alkyl, m is 3, n
The compound according to claim 1, wherein is 1. 12, Y is oxygen, X is hydrogen, Xl is chlorine, RIIJ'-chlorine or methyl, R1 is halogen or C1-C, alkyl, R3 is c, -c,
The compound according to claim 1, which is alkyl, mIJ''-3, and n is 1. 1 & Y are oxygen, X and Xl are fluorine, Ro is chlorine or methyl, 2. A compound according to claim 1, wherein R7 is norogen or C5-C, alkyl, R8 is C+''-C4 alkyl, m is 3, and n is 1. 14, Y is oxygen, X is hydrogen or halogen,
Xo is halogen, R1 is chlorine or methyl,
2. A compound according to claim 1, wherein R2 is halogen or C0-C4 alkyl, R5 is C1-C4 alkyl, m is 3, and n is 2. 15, Y is oxygen, X is halogen, Xo is chlorine, R is dechloride or methyl, R2 is halogen or 01-C4 alkyl, R8 is C8-C4 alkyl, The compound according to claim 1, wherein m is 6 and n is 2. 16, Y is oxygen, X and Xl are fluorine,
R1 is chlorine or methyl, R, is halogen or C1
-C4 alkyl, R3 is 01-C4 alkyl, rniJ''-3, and n is 2. 17. Y is oxygen, and X and Xo are It is fluorine,
The compound according to claim 1, wherein R1 and R7 are chlorine or methyl, R8 is methyl, m is 3, and n h''-1. 18, Y is oxygen, X and X' is fluorine,
2. A compound according to claim 1, wherein R+ and R1 are chlorine or methyl, R3 is methyl, m is 3, and n is 2. 19 Y is oxygen, X is halogen, X' is chlorine, R1 and Rt are chlorine or methyl,
The compound according to claim 1, wherein R1 is methyl, m is 3, and +1 is 2 [I Y is lW, X is hydrogen, and X' is chlorine] , R1 and R2 are chlorine or methyl, Rs is methyl,
The compound according to claim 1, wherein m is 3 and n is 2. 2t 1-(4-(2,4-dimethylphenoxy)-3
,6-dimethyl-5-chlorophenyl]-3-(2-chlorobenzoyl)urea, 1-[:4-(2,4-dimethylphenoxy)-3,
6-dimethyl-5-chlorophenyl]-3-(2,6-
Chlorobenzoyl) urea. 1-(4-(5,s-dimethylphenoxy)-3,6
=dimethyl-5-chlorophenyl')-(2,6-chloroolbenzoyl)urea, 1-(4-(2-methyl-4-bromphenoxy)-3
, 6-dimethyl-5-chlorophenyl]-3-(2-chlorobenzoyl)urea, 1-[4-(2-methyl-4-bromphenoxy)3.
6-dimethyl-5-chlorophenyl]-3-(2,6-
chlorobenzoyl)urea, 1-(4-(2-methyl-4-chlorophenoxy)-6-dimethyl-5-chlorophenyl]-3-(2-chlorobenzoyl)urea, 1-(4-(2- Methyl-4-chlorophenoxy)-3
,6-dimethyl-5-chlorophenyl]-3-(2,6
-chloroolbenzoyl) urine i. 1-(4-(2-methyl-4-t-butylphenoxy)
-3,6-dimethyl-5-chlorophenyl]-5-(
2,6-difluorobenzoy/I/) urea. 1-(4-(2,3,s-)dimethylphenoxy)
-6,6-dimethyl-5-chlorophenyl)-3'-(
2,6-chloroolbenzoyl) urine? , 1- [4-(
3,5-dimethyl-4-chlorophenoxy)-5,6-
Shimejiru 5-chlorophenyl]-5-(2,6-';
'Fluorobenzoyl)urin, 1-[4-(2,5-
dimethyl-4-pro15phenoxy)-3,6-dimethyl-5-chlorophenyl]-ro-(2-chlorobenzoyl)urea, 1-[4-(2,5-dimethyl-4-chlorophenoxy)-3 ,6-dimethyl-5-chlorophenyl]-3-(2,(S-chloroolbenzoyl)5y,
1-(4-(2,5-dimethylphenoxy)-3,6
-dimethyl-5-chlorophenyl]-3-(2,6-chloroorpensoyl)urea, 1-[4-(2,5-dimethylphenoxy)-3,
(S-dimethyl-5-chlorophenyl]-3-(2-chlorobenzoyl)urea, 1-(4-(2,4,5-trimethylphenoxy)-
3,6-dimethyl-5-chlorophenyl]-3-(2,
6-Chlorobenzoyl)urea, 1-(4-2,4
,5-)dimethylphenoxy)-ro. 6-dumeblue 5-chlorophenyl)-3-(2-chlorobenzoyl)urea, j-[4-(2,5-dimethyl-4-bromphenoxy)-5,6-dimethyl-5-chlorophenyl]-3 −
(2,6-chloroolbenzoyl)urea, 1-[4-
(2,5-dimethyl-4-cyanophenoxy)-1,6
-Simethyl-5-chlorophenoxy]-3-(2,6-
chloroolbenzoyl) I'RfE, or j-(4-(
2,5-dimethyl-4-trifluoromethylphenoxy)-a6-dimethyl-5-chlorophenyl)-3-(2
, 6-chloroolbenzoyl) urea. 2. A pesticide comprising the compound described in Claims 1 to 7. benzoyl isocyanate or benzoylisothiocyanate, - and alkyl phenoxyaniline of the formula (where x, x', Y,
Claim 1 consisting of reacting R+, R2, Rs, m and n with % as specified in Claim 1) and then recovering the desired product.
A method for producing the compound described in Section 1. 24, an alkyl phenoxy phenyl isocyanate or alkyl phenoxy phenyl thiocyanate of the formula and a benzamide of the formula (where X, X', Y, R,, R
t, R3, m and n are as defined in claim 1) and then recovering the desired product. How to manufacture.