PESTICIDAL 1-(ALKYL-PHENOXYARYL)-3-BENZOYL UREAS AND PROCESS FOR PREPARATION

Abstract: 1-(alkylphenoxyphenyl)-3-benzoyl ureas and a process for their preparation are provided. The ureas are useful as the active toxicant in pesticidal composition. The ureas have the general formula: wherein X, X′ independently hydrogen, halogen, C₁-C₄ alkyl. haloalkyl, polyhaloalkyl, alkoxy. polyhaloalkoxy Y represents oxygen or sulfur; m, n are independently 0-4; R₁ represents hydrogen, halogen, C₁-C₄ alkyl, haloalkyl, polyhaloalkyl, or alkoxy, R₂ represents hydrogen, halogen, C₁-C₄ alkyl, polyhalo­ alkyl, polyhaloalkoxy, C₁-C₈ alkylsulfonyl, C₁-C₈ alkoxy, C₁-C₈ alkylthio, C₁-C₈ dialkylamino, CN, NO₂, CO₂R₄, or CONHR₄ wherein R₄ represents C₁-C₈ alkyl; and R₃ represents C₁-C₁₂ alkyl, with the proviso that m may not be 0 or 1 when n is less than 2.

Description: PESTICIDAL 1-(ALKYL- PHENOXYARYL) - 3 -BENZOYL UREAS AND PROCESS FOR PREPARATION This invention relates in general to l-(alkyl-phenoxyaryl)-3-benzoyl ureas and to a process for their preparation. In one aspect, this invention relates to benzoyl ureas which are useful as pesticides. Prior to the present invention a few benzoyl ureas had been reported in the patent literature as having pesticidal activity. For exampie. U.S. -A-- 3,992,553 which issued on November 16. 1976, and U.S. -A- 4,041,177 which issued on August 9, 1977, both disclosed certain benzoylureido-diphenyl ethers which were indicated to possess insecticidal properties. Similarly, U.S. -A- . 3,748,356 and 3,933,908 also disclosed certain substituted benzoyl ureas and stated that the compositions had strong insecticidal activity. U.S. -A- 4,148.902 which issued April 10. 1979 discloses substituted ((phenylamino)carbonyl) pyridine carboxamides and claims a method of controlling insects in addition to the compositions themselves. Additional disclosures of benzoyl ureas in the patent literature are found in U.S. -A- 4,166.124: 4.083,977: 4.160,834: 4,264,605 4,064,267: and 4,005,223t 4,123,449; 4,068,002; 4,194.005; 4,275,077; 4,173,639; 3,989,842S Ger. Offen. 2,901,334 (EP 013-414); and DE 3,104,407 (EP 57-888). Accordingly, one or more of the following objects can be achieved by the practice of this invention. It is an object of this invention to provide l-(alkylphenoxyaryl)-3-benzoyl ureas. Another object of this invention is to provide certain l-(alkylphenoxyphenyl)-3-benzoyl ureas which exhibit excellent insecticidal activity. A still further object of this invention is to provide benzoyl ureas, such as, l-[2,4-dimethylphenoxy-3,6- dimethyl-5-chlorophenyl]-3-(2,6-difluorobenzoyl) urea, and 1-14-(2,5-dimethyl-4-chlorophenoxy)-3,6-dimethyl-5- chlorophenyl]-3-(2,6-difluorobenzoyl)urea Another object is to provide processes for the preparation of these benzoyl ureas. Further object is to provide pesticidal compositions containing these benzoyl ureas as the active toxicant. Another object of the invention is to provide a method for controlling pests by the application of these pesticidal compositions. These and other objects will readily become apparent to those skilled in the art in the light of the teachings herein set forth. In its broad aspect the invention relates to l-(alkylphenoxyaryl)-3-benzoyl ureas, pesticidal compositions containing the same, and processes for their preparation and use. The benzoyl ureas of this invention can be represented by the following formula: EMI3.1 <tb> <SEP> x <SEP> O <SEP> Y. <SEP> FORMULA <SEP> 1 <tb> t <SEP> NH <SEP> N <SEP> H < < to <SEP> XR3 <tb> <SEP> (R1)m <SEP> (R2) <SEP> n <tb> <SEP> (R1)m <SEP> (R2)n <tb> Wherein X, X' are independently hydrogen, halogen, C1-C4 alkyl, - --haloalkyl, polyhaloalkyl, alkoxy, polyhaloalkoxy Y represents oxygen or:sulfur; m, n are O - 4 t R1 represents hydrogen, halogen, C1-C4 alkyl, haloalkyl, polyhaloalkyl, alkoxy, R2 represents hydrogen, halogen, C1-C4 alkyl, polyhaloalkyl, polyhaloalkoxy, C1-C8 alkylsulfonyl, C1-C8 alkoxy, Cl-C8 alkylthio, C1-C8 dialkylamino, CN, NO2, CO2R4, CONHR4 wherein R4 represents C1-C8 alkyl; and R3 represents C1-C12 alkyl, with the proviso that m may not be O or 1 when n is less than 2. As indicated above, the invention relates to 1-(alkyl-phenoxyaryl)-3-benzoyl ureas, pesticidal compositions containing the same, and processes for their preparation and use. Preferred benzoyl urea compounds within the broad generic formula 1 are those having the formulae: EMI4.1 wherein X. X1, Y. R1, R2, R3. n and m are as indicated above. Particularly preferred benzoyl ureas are those of the formulae: EMI5.1 EMI6.1 Wherein X; X', Y, R1, R2 and R3 are as indicated above. The following benzoyl urea compounds are illustrative of those encompassed by the above formulae and which can be prepared by the practice of this invention: 1-[4-(2-methyl-3,4-dichlorophenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2,6-difluorobenzoyl)urea. 1-[4-(2-methyl-3,4-dichlorophenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2-chlorobenzoyl)urea. 1-14-(2-methylphenoxy)-3.6-dimethyl-5-chlorophenyll- 3-(2.6-difluorobenzoyl)urea, 1-[4-(2-methylphenoxy)-3,6-dimethyl-5-chlorophenyl] 3-(2,6-dichlorobenzoyl)urea 1-[4-(2-methylphenoxy)-3,6-dimethyl-5-chlorophenyl] 3-(2-chlorobenzoylXurea. 1-[4-(2-methylphenoxy)-3,6-dimethyl-5-chlorophenyl] 3- (2-chlorobenzoyl)thiourea. 1-[4-(2-methylphenoxy)-3,6-dimethyl-5-chlorophenyl] 3-(t-methylbenzoyl)thiourea, 1-[4-(2-methylphenoxy)-2,3,5,6-tetramethylphenyl]-3 (2. 6-dimethylbenzoyl)urea. 1-[4-(2-methylphenoxy)-2,3,5,6-tetramethylphenyl]-3 (2,6-methylbenzoyl)thiourea, 1-14-(2-methylphenoxy)-2,3,5,6-tetramethylphenyll-3- (2,6-difluorobenzoyl)urea, 1-[4-(2-methylphenoxy)-2,3,5,6-tetramethylphenyl]-3 (2,6-dichlorobenzoyl)urea, 1-[4-(2-methylphenoxy)-2,3,5-trimethylphenyl]-3-(2,6 dichlorobenzoyl)urea, 1-[4-(2-methylphenoxy)-3,5-dichlorophenyl]-3-(2,6 difluorobenzoyl) urea, 1-14-(2-methyl-4-bromophenoxy)-3,6-dimethyl-5- chlorophenyl]-3-(2,6-difluorobenzoyl)urea, 1-[4-(2-methyl-4-bromophenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2-chlorobenzoyl)urea, 1-[4-(2-methyl-4-bromophenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2-chlorobenzoyl)thiourea, 1-14-(2-methyl-4-bromophenoxy)-3,6-dimethyl-5- chlorophenyl]-3-(2-methylbenzoyl)thiourea, 1-[4-(2-methyl-4-bromophenoxy)-2,3,5,6-tetramethyl phenyl]-3-(2,6-diflorobenzoyl)urea, l-t4-(2-methyl-4-bromophenoxy)-2,3,5-tetramethyl- phenyl]-3-(2,6-difluorobenzoyl)urea, 1-14-(2-methyl-4-bromophenoxy)-3,5-dimethylphenyll-3- (2,6-difluorobenzoyl)urea, l-(4-(2-inethyl-4-broinophenoxy)-3,5-dichlorophenylJ-3 (2-chlorobenzoyl)urea, 1-[4-(2-bromo-4-methylphenoxy)-3,6-dimethyl-5 chlorophenyl]-3- (2,6-difluorobenzoyl)urea, 1-[4-(2-bromo-4-methylphenoxy)-3,6-dimethyl-5 chlorophenyll-3-(2-chlorobenzoyl)urea, 1-14-(2-bromo-4-methylphenoxy)-2,3,5,6-tetramethyl- phenyl]-3-(2-chlorobenzoyl)urea, -14-(2-bromo-4-methylphenoxy)-3,5-dichlorophenyl]-3- (2,6-difluorobenzoyl)urea, 1-[4-(2-bromo-4-methylphenoxy)-3,5-dimethylphenyl]-3 (2-methylbenzoyl)thiourea, 1-[4-(2-methyl-4-t-buthylphenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2,6-difluorobenzoyl)urea, 1-[4-(2-methyl-4-t-buthylphenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2-chlorobenzoyl)urea, 1-[4-(2-methyl-4-t-buthylphenoxy)-2,3,5,6-tetramethyl phenyl]-3-(2,6-difluorobenzoyl)urea, 1-[4-(2-methyl-4-t-buthylphenoxy)-3,5-dichlorophenyl] 3-(2-methylbenzoyl)thiourea, 1-[4-(2-methyl-4-chlorophenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2,6-difluorobenzoyl)urea, 1-[4-(2-methyl-4-chlorophenoxy)-3,5-dichlorophenyl] 3-(2-methylbenzoyl)thiourea, 1-[4-(2-methyl-4-chlorophenoxy)-2,3,5,6-tetramethyl-5 phenyl]-3-(2,6-dimethoxybenzoyl)urea, 1-[4-(2-methyl-4-chlorophenoxy)-3,6-dimehtyl-5 chlorophenyl]-3-(2,6-dimethoxylbenzoyl)urea, 1-[4-(4-nonyphenoxy)-3,5-dichlorophenyl]-3 (2,6-diflorobenzoyl)urea, 1-[4-(4-nonyphenoxy)-2,3,5,6-tetramethylphenyl]-3 (2-chlorobenzoyl)thiourea, 1-[4-(4-nonyphenoxy)-3,5-dichlorophenyl]-3-(2,6 diflorobenzoyl)urea, 1-[4-(4-nonylphenoxy)-3,5-dimethylphenyl]-3-(2-methyl benzoyl)urea, 1-[4-(2-chloro-4-methylphenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2,6-difluorobenzoyl)urea, 1-[4-(2-chloro-4-methylphenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2-chlorobenzoyl)thiourea, 1-[4-(2-chloro-4-methylphenoxy)-3,5-dichlorophenyl] 3-(2,6-difluororobenzoyl)urea, 1-[4-(2-chloro-4-methylphenoxy)-2,3,5,6-tetramethyl phenyl]-3-(2,6-difluororobenzoyl)urea, 1-[4-(3,4,5-trimethylphenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2,6-difluororobenzoyl)urea, 1-[4-(3,4,5-trimethylphenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2-chlorobenzoyl)thiourea, 1-[4-(3,4,5-trimethylphenoxy)-2,3,5,6-tetramethyl phenyl]-3-(2-methylbenzoyl)thiourea, 1-[4-(3,4,5-trimethylphenoxy)-3,5-dichlorophenyl]-3 (2,6-difluororobenzoyl)urea, 1-[4-(2,3,5-trimethylphenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2,6-dimethoxybenzoyl)urea, 1-[4-(3,4,5-trimethylphenoxy)-2,3,5,6-tetramethyl phenyl]-3-(2,6-difluorobenzoyl)urea, 1-[4-(3,4,5-trimethylphenoxy)-3-i-propylphenyl)-3 (2-methylbenzoyl)thiourea, 1-[4-(3,4,5-trimethylphenoxy)-3-trifluoromethyl phenyl]-3-(2,6-difluorobenzoyl)urea, 1-l4-(2-methyl-4-trifluoromethylphenoxy)-3,6-dimethyl 5-chlorophenyl]-3-(2,6-difluorobenzoyl)urea, l -(2-methyl-4-trifluoromethylphenoxy)-3,6-dimethyl- 5-chlorophenyl] -3- (2-chlorobenzoyl) thiourea, 1-[4-(2-methyl-4-trifluoromethylphenoxy)-3,5 dichlorophenyl]-3-(2,6-dimethoxybenzoyl)urea, 1-[4-(2-methyl-4-trifluoromethylphenoxy)-2,3,5 trimethylphenyl]-3-(2-methoxybenzoyl)thiourea, 1-[4-(2,4-dimethylthiophenoxy)-2,3,6-trimethylphenyl]-3 (2-chlorobenzoyl) urea, 1-14-(3,5-dimethylphenoxy)-2,6-dimethylphenyl]-3- (2,6-difluorobenzoyl)urea, l-t4-(2-methyl-4-methoxyphenoxy)-3,6-dimethyl-S- chlorophenyl]-3-(2,6-difluorobenzoyl)urea, 1-14-(2-methyl-4-dimethylaminophenoxy)-3,6-dimethyl- 5-chlorophenyl]-3-(2,6-difluorobenzoyl)urea, 1-[4-(2-methyl-4-methylthiophenoxy)-3,6-dimethylphenyl-5 chlorophenyl]-3-(2,6-difluorobenzoyl)urea, 1-t4-t2-methyl-4-methylsulfonylphenoxy)-3,6-dimethyl -5-chlorophenyl]-3-(2,6-difluorobenzoyl)urea, 1-14-(2-methyl-4-dimethylaminophenoxy)-3,5-dimethyl- phenyl]-3-(2-methylbenzoyl)urea, 1-[4-(2-methyl-4-methylthiophenoxy)-3-chloro-6-methyl phenyl]-3-(2-methylbenzoyl)urea, l-t4-(2-methyl-4-methoxyphenoxy)-3,6-dimethyl-5- chlorophenyl]-3-(3,4-dichlorobenzoyl) urea, 1-14-(2,3-dimethyl-4-Sromophenoxy)-3,6-dimenthyl-S- chlorophenyl]-3-(2-chlorobenzoyl) urea, 1-[4-(2,5-dimethyl-4-chlorophenoxy)-3,6-dimethyl-S- chlorophenyl]-3-(2,6-difluorobenzoyl) urea, 1-l4-(2,5-dimethylphenoxy)-3,6-dimethyl-5-chloro- phenyl]-3-(2,6-difluorobenzoyl) urea, 1-[4-(2,5-dimethylphenoxy)-3,6-dimethyl-S-chloro- phenyl]-3-(2-chlorobenzoyl) urea, 1-[4-(2,5-dimethyl-4-ethoxycarbonylphenoxy)-3-6-di- methyl-5-chlorophenyll-3-(2,6-diflurobenzoyl)urea, 1-[4-(2,5-dimethyl-4-ethoxycarbonylphenoxy)-3,6- dimethyl-5-chlorophenyl]-3-(2-chlorobenzoyl)urea, 1-[4-(2-methyl-4-trifluoromethylphenoxy)-3,6-dimethyl- 5-chlorophenyl] -3- (2-chlorob±nzoyl) urea, l-[4-(2,5-dimethyl-4-trifluromethylphenoxy)-3,6-di- methyl-5-chlorophenyll-3-(2,6-difluorobenzoyl)urea, 1-[4-(2,5-dimethyl-4-trifluromethylphenoxy)-3,6-di- methyl-5-chlorophenyl]-3-(2-chlorobenzoyl)urea, l-t4-(2,5-dimethyl-4-trifluoromethoxyphenoxy)-3,6-di- methyl-5-chlorophenyl]-3-(2,6-diflorobenzoyl)urea, 1-14-(2,5-dimethyl-4-trifluromethoxyphenoxy)-3,6-di- methyl-5-chlorophenyl]-3-(2-chlorobenzoyl)urea, 1-[4-(2,5-dimethyl-4-methoxyphenoxy)-3,6-dimethyl-5- chlorophenyl) -3- (2,6-diflurobenzoyl) urea, 1-[4-(2,5-dimethyl-4-methoxyphenoxy)-3,6-dimethyl-5- chlorophenyl]-3-(2-chlorobenzoyl)urea, 1-[4-(3,5-dimethyl-4-chlorophenoxy)-3,6-dimethyl-S- chlorophenyl]-3-(2,6-diflorobenzoyl)urea, 1-14-(2,4,5-trimethylphenoxy)-3,6-dimethyl-5-chloro- phenyl)-3-(2,6-difluorobenzoyl)urea, 1-14-(2,4,5-trimethylphenoxy)-3,6-dimethyl-5-chloro- phenyl)-3-(2-chlorobenzoyl)urea, 1-[4-(2,5-dimethyl-4-bromophenoxy)-3,6-dimethyl-5- chlorophenyl]-3-(2,6-difluorobenzoyl)urea, 1-14-(2,5-dimethyl-4-cyanophenoxy)-3,6-dimethyl-5- chlorophenyl]-3-(2,6-diflorobenzoyl)urea, 1-[4-(2,5-dimethyl-4-cyanophenoxy)-3,6-dimethyl-5 chlorophenyll-3-(2-chlorobenzoyl)urea, I-t4-(2-methyl-4-cyanophenoxy)-3,6-dimethyl-S-chloro- phenyll-3-(2,6-diflurobenzoyl)urea, l-t4-(2-methyl-4-cyanophenoxy)-3,6-dimethyl-5-chloro- phenyll-3-(2-chlorobenzoyl)urea, 1-[4-(2,4-dimethylphenoxy)-3,6-dimethyl-5-chloro- phenyl]-3-(2,6-difluorobenzoyl)urea, 1-l4-(2,4-dimethylphenoxy)-3,6-dimethyl-5-chloro- phenyll-3-(2-chlorobenzoyl)urea, 1-[4-(2,5-dichloro-4-methylphenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2,6-difluorobenzoyl)urea, 1-[4-(2,5-dichloro-4-methylphenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2-chlorobenzoyl)urea, 1-14-(2-methyl-4,5-dichlorophenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2,6-difluorobenzoyl)urea, l-t4-(2-methyl-A,5-dichlorophenoxy)-3,6-dimethyl-S- chlorophenyl]-3-(2-chlorobenzoyl)urea, and 1-[4-(2,5-dimethyl-4-chlorophenoxy)-3-methylphenyl]-3 (2,6-difluorobenzoyl)urea. The . benzoyl ureas of this invention can'be conveniently prepared by one or more methods. For example, the compounds of this invention may be prepared by reacting a alkylphenoxyaniline (9) with a benzoyl isocyanate or benzoyl isothiocyanate (10) according to Scheme I. EMI13.1 <tb> <SEP> X <SEP> O <SEP> SCHEME <SEP> I <tb> <SEP> OxiNCY <SEP> + <SEP> H2Nw <SEP> (R2)n <tb> <SEP> (10) <SEP> (R1)m <SEP> (9) <tb> <SEP> 0 <SEP> Y <tb> organic <SEP> XNHANH/OX <tb> solven(A <tb> <SEP> (R1)m <SEP> (1) <tb> <SEP> (R1)m <SEP> (1) <tb> Wherein: X. X'. Y'. R1, R2. R3, m. and n have the meaning given to Formula (1). Alternatively. the - compounds may be prepared by the reaction of an alkylphenoxyphenylisocyanate (12) with a benzamide (11) according to Scheme II. SCHEME II EMI13.2 Whrein:X,X',Y,R1,R2,R3,m, and n have the meaning given to Formula (1). In general, the reactions illustrated in Schemes I and II can be carried out in organic solvents such as aromatic hydrocarbons br halogenated hydrocarbons. Solvents like toluene and l.2-dichloroethane are preferred. These reactions proceed at temperatures ranging from room temperature to 150' C. The intermediates shown in Schemes I and II can be prepared according to generally accepted procedures. Thus. the substituted benzoyl isocyanate (10) can be prepared from the corresponding benzamide following the general procedure of Speziale et. al.. J. Orv. Chem. 3742 (1962). EMI14.1 <tb> <SEP> x <SEP> x <tb> 0 <SEP> CI <SEP> Cl <SEP> vNCY <tb> <SEP> solvent <SEP> A <tb> x <SEP> where <SEP> Y= <SEP> oxygen <SEP> X1 <SEP> (10) <tb> The substituted benzoyl isothiocyanate (10) can be prepared from the corresponding acid chloride with-potassium thiocyanate. This procedure in general is similar to that employed by Ambelang, et. al J. Amer. Chem. Soc.. 61. 632 (1937). The aniline (9) can be prepared according to Scheme III shown below. SCHEME III EMI15.1 Wherein R1. R2, R3. m and n have the meaning given to Formula 1. The reaction of substituted chloronitrobenzene (13) with substituted phenol (14) proceeds in the presence of base at elevated temperature to give the substituted nitroether (15). The reduction of nitroether (15) to aniline (9) can be achieved under hydrogen atmosphere using a heterogeneous hydrogenation catalyst. Suitable catalyst includes platinum or palladium on carbon or Raney nickel. The pressure ranging from 20 100 PSI at ambient temperature can be applied. Suitable, solvents include aromatic hydrocarbon or alcohol. The reduction of nitroether (15) to aniline (9) can also be achieved by chemical method using the procedure of E. Enders, et. al., GB-A-1,456,964. The intermediates such as substituted chloronitrobenzene and substituted phenol are available commercially or may be prepared by well known method from chemical literature. One particular chloronitrobenzene (16) was prepared by the route outlined in Scheme IV. SCHEME IV EMI16.1 <tb> CH3 <SEP> 3 <SEP> CH3 <SEP> Cl <tb> isomer <SEP> CH3 <tb> CH3- <SEP> CH3 <SEP> \ <SEP> SCl <tb> <SEP> CH3 <tb> <SEP> (16) <tb> The aniline (9) can be converted to the isocyanate or isothiocyanate (12) by the reaction with phosgene or thiophosgene as shown below: EMI16.2 Wherein: Y, R1, R2a R3. m. and n have the meaning given to Formula 1. The compounds contemplated in this invention may be employed as insecticides according to methods known to those skilled in the art. Pesticidal compositions containing the compounds as the active toxicant will usually comprise a carrier and/or diluent. either liquid or solid. Suitable liquid diluents or carriers include water. petroleum distillates. or other liquid carriers with ot without surface active agents. Liquid concentrates may be prepared by dissolving one of these compounds with a nonphytotoxic solvent such as acetone, xylene, nitrobenzene. cyclohexanone or dimethyl formamide and dispersing the toxicants in water with the aid of suitable surface active emulsifying and dispersing agents. The choice of dispersing and emulsifying agents and the amount employed is dictated by the nature of the composition and the ability of the agent to facilitate the dispersion of the toxicant. Generally. it is desirable to use as little of the agent as is possible. consistent with the desired dispersion of the toxicant in the spray so that rain does not re-emulsify the toxicant after it is applied to the plant and wash it off the plant. Nonionic, anionic. or cationic dispersing and emulsifying agents may be employed. for example. the condensation products of alkylene oxides with phenol and organic acids. alkyl aryl sulfonates, complex ether alcohols. or quaternary ammonium compounds. In the preparation of wettable powder or dust or granulated compositions, the active ingredient is dispersed in and on an appropriately divided solid carrier such as clay. talc. bentonite. diatomaceous earth. or fullers earth. In the formulation of the wettable powders the aforementioned dispersing agents as well as lignosulfonates can be included. The required amount of the toxicants contemplated herein maybe applied per acre treated in from 1 to 200 gallons or adore of liquid carrier and/or diluent or in from 5 to 500 pounds of inert solid carrier and/or diluent. The concentration in the liquid concentrate will usually vary from - -10 to 95 percent by weight and in the solid formulations from 0.5 to - 90 percent by weight. Satisfactory sprays. dusts. or granules for general use contain from 1/4 to 15 pounds of active toxicant per acre. The pesticides contemplated herein prevent attack by insects upon plants or other material to which the pesticides are applied, and they have rel-at--ively high residual toxicity. With respect to plants. they have a high margin of safety in that when used in sufficient amount to-kill or repel the insects. they do not burn or injure the plant. and they resist weathering which includes wash-off caused by rain, decomposition by ultraviolet light. oxidation, or hydrolysis in the presence of moisture or. at least, such decomposition, oxidation, and hydrolysis as would materially decrease the desirable pesticidal characteristic of the toxicants or impart undesirable characteristics, for instance, phytotoxicity. to the toxicants. The toxicants are so chemically inert that they are now compatible with substantially any other constituents of the spray schedule. and they may be used in the soil, upon the seeds. or the roots of plants without insuring either the seeds or roots of plants. Mixtures of the active compounds may be employed if desired as well as combinations of the active compounds of this invention with other biologically active compounds or ingredients. The following examples illustrate the best node presently contemplated for the practice of the invention: Example 1 Preparation of 4-(2,4-dimethylphenoxy)-3,6 dimethvl-5-chloronitrobenzene . To a flask equipped with condenser. sti-r-rer, under nitrogen, was added 3,6-dimethyl-4,5-dichloronitrobenzene (50g. 0.23 mol). 2.4-dimethylphenol (38.5g, 0.32 mol). potassium carbonate (50g. 0.36 mol), and dimethylformamide (125ml). The resulting mixture was heated at 90#100 for 72 hours. It was then cooled, filtered. and concentrated to give dark oil. It was partitioned between toluene (300 ml) and 4 sodium hydroxide (250 ml) and then separated. The organic Layer was washed with water and brine, dried (N2SO4) and concentrated to give dark oil. Solid was formed after the oil vas trituated with hexane. The solid was washed with cold hexane and vacuum dried to give a tan powder (47.8g. 0.16 mol); mp 78 #80 . Anal: C16H16C1N03 Calcd: C, 62.85: H. 5.27; -N. 4.58 Found C, 63.47:H. 5.35; N, 4.49 Example 2 A. Preparation of 4-(2,4-dimethylphenoxy) 3,6-dimethyl-5-chloroaniline To a solution of 4-(2,4-dimethylphenoxy)3,6-dimethyl-5-chloronitrobenzene (25g. 81.8 mmol in toluene (250 nl) was added 5% platinum on carbon (l.Og). The resulting fixture was subjected to hydrogenation at 20 psi. After 4.5 hours a the reaction mixture was filtered through celite and concentrated to given an oil (24.5g). It turned to a pinkish solid after high vacuum drying; mp 86#88 C. Anal: C16H18C1NO Calcd: C, 69.69; H, 6.53; N.5.08 Found: C. 70.02; H3 6.60; N, 5.68 B. Preparation of 4-(3-methvl-4-methvl- thiophenoxy)-3,6-dimethyl-5 chloroaniline To a solution of 4-(3-nethyl-4-methylthio- phenoxy)-3,6-dimethyl-5-chloronitrobenzene (5.0 g. 14.8 mmol) in 7.5 nil of p-dioxane was added SnCl2 2H2O (10.0 g. 44.4 mmol) and concentrated HC1 (10.5 ml). The resulting mixture was heated up to reflex for 65 in., cooled. and poured into a fixture of NaCH (20 g). H20 (50 ml). and ice (50 g). The mixture was extracted twice with toluene. The combined organic extracts were washed with 4% NaOH, H2O. and brine. It was then dried (Na2SO4) and concentrated to yield a yellow oil. Solid formed after the oil was chilled and trituated with cold hexane and a trace of ethyl acetate. The solid was filtered and washed with -hexane to give a beige powder (3.06 g. 9.9 mmol): nip 80-86 C (decomp.). Anal: C16H18CINOS Calcd: C. 62.34: H, 5.89: N, 4.55 Found: C, 62.38; H. 5.89; N. 4.25 Example 3 Preparation of 1-(2-Chlorobenzoyl)-3 [4-(2,4-dimethylphenoxy)-3,6-dimethyl-5-chloroaniline urea. To a warm solution of 4.94 g (17.9 mmol) of 4-(2,4-dimethylphenoxy)-3,6-dimethyl-5-chloroaniline in 12.5 ml of toluene was added 4.21 g of 2-chlorobenzoyl isocyanate in 1.5 ml of toluene. The resulting solution was heated at 90 for 0.5 hour. It was then cooled and diluted with 5 ml of hexane. The mixture was filtered and the solid was washed with 50% hexane in toluene. A white solid (6.32g, 13.8 mmol) was obtained after vacuum dried at 80 overnight; mp 163-165 C. Anal: C24H22C12N203 Calcd: C. 63.03; H. 4.85; N. 6.12 Found: C. 63.33; H, 4.94: N, 6.09 Examples 4 - 216 In a manner similar to that employed in the preceding examples. and using one of the synthesis schemes previously disclosed. other urea compounds were prepared. The identity of the substituents on the generic formula and the analytical data are set forth in table I below: : TABLE 1 1-(Alkylphenoxyaryl)-3-Benzoyl Ureas Calculated Found Example Molecular Formula XX' Y R1 R2 R3 C H N C H N 1 C22H16Cl2F2N2O3 2,6-F2 O 3,5-Cl 2-CH3 4-CH3 56.79 3.47 6.02 56.61 3.35 6.08 2 C22H17Cl3N2O3 2-Cl O 3,5-Cl 2-CH3 4-CH3 56.97 3.70 6.04 36.84 3.61 6.02 3 C22H16Cl4N2O3 2,6-Cl2 O 3,5-Cl 2-CH3 4-CH3 53.03 3.24 5.62 32.38 3.13 5.72 4 C24H22F2N2O3 2,6-F2 O 3,5-(CH3)2 2-CH3 4-CH3 67.91 3.23 6.60 67.23 5.10 6.62 5 C24H22ClFN2O3 2,6-ClF O 3,5(CH3)2 2-CH3 4-CH3 65.35 5.03 6.35 65.22 5.03 6.29 6 C24H23ClN2O3 2-Cl O 3,5(CH3)2 2-CH3 4-CH3 68.16 5.47 6.63 68.12 3.58 6.48 7 C24H22Cl2N2O3 2,6-Cl2 O 3,5(CH3)2 2-CH3 4-CH3 63.02 4.85 6.13 38.72 4.16 6.33 8 C24H22Cl2N2O3 2-Cl O 3,5,6-CH3ClCH3 2-CH3 4-CH3 63.03 4.85 6.12 63.33 4.94 6.09 9 C24H21Cl3N2O3 2,6-Cl2 O 3,5,6-CH3ClCH3 2-CH3 4-CH3 58.61 4.30 5.70 38.28 4.21 5.64 10 C24H21Cl2FN2O3 2,6-ClF O 3,5,6-CH3ClCH3 2-CH3 4-CH3 60.64 4.45 5.89 60.79 4.42 5.82 11 C24H21ClF2N2O3 2,6-F2 O 3,5,6-CH3ClCH3 2-CH3 4-CH3 62.82 4.61 6.10 62.94 4.88 6.03 12 C22H15Cl5N2O3 2-Cl O 3,5-Cl2 2,3,4-CH3ClCl 5-CH3 49.61 2.84 5.26 49.99 2.90 5.21 13 C22H14Cl6N2O3 2,6-Cl2 O 3,5-Cl2 2,3,4-CH3ClCl 5-CH3 46.60 2.49 4.94 46.27 2.53 4.94 14 C22H14Cl5FN2O3 2,6-ClF O 3,5-Cl2 2,3,4-CH3ClCl 5-CH3 47.99 2.56 5.09 47.21 2.80 5.01 15 C22H14Cl4F2N2O3 2,6-F2 O 3,5-Cl2 2,3,4-CH3ClCl 5-CH3 49.47 2.64 5.24 49.44 2.74 5.17 16 C24H22Cl2N2O2S 2-Cl O 3,5,6-CH3ClCH3 2-CH3 4-CH3 60.89 4.60 3.92 61.13 4.83 6.03 17 C24H22Cl2N2O3 2-Cl O 3,5,6-CH3ClCH3 3-CH3 5-CH3 63.03 4.85 6.12 62.64 4.73 6.40 18 C24H22Cl2N2O2S 2-Cl O 3,6-(CH3)2-5-Cl 3-CH3 5-CH3 60.89 4.68 5.92 61.12 4.73 5.94 19 C24H21Cl3N2O3 2,6-Cl2 O 3,6-(CH3)2-5-Cl 3-CH3 5-CH3 58.61 4.30 5.70 38.41 4.26 5.71 20 C24H21ClF2N2O3 2,6-F2 O 3,6-(CH3)2-5-Cl 3-CH3 5-CH3 62.82 4.61 6.10 63.23 4.67 6.08 21 C26H26Cl2N2O3 2-Cl O 3,6-(CH3)2-5-Cl H 4-t-butyl 64.34 5.40 5.77 64.03 5.36 5.98 22 C26H26Cl2N2O2S 2-Cl O 3,6-(CH3)2-5-Cl H 4-t-butyl 62.27 5.23 5.59 62.06 5.43 5.79 TABLE 1 (Cont'd) 1-(Alkylphenoxyaryl)-3-Benzoyl Ureas Calculated Found Example Molecular Formula XX' Y R1 R2 R3 C H N C H N 23 C26H25Cl3N2O3 2,6-Cl2 O 3,6-(CH3)2-5-Cl H 4-t-butyl 60.07 4.85 5.39 60.23 4.92 3.30 24 C26H25ClF2N2O3 2,6-F2 O 3,6-(CH3)2-5-Cl H 4-t-butyl 64.14 5.17 5.75 64.40 5.32 3.73 25 C23H20Cl2N2O3 2-Cl O 3,6-(CH3)2-5-Cl H 4-CH3 62.31 4.55 6.32 62.22 4.66 6.23 26 C23H20Cl2N2O2S 2-Cl S 3,6-(CH3)2-5-Cl H 4-CH3 60.13 4.39 6.10 59.84 4.38 3.90 27 C23H19Cl3N2O3 2,6-Cl2 O 3,6-(CH3)2-5-Cl H 4-CH3 57.82 4.01 5.86 58.09 4.02 5.85 28 C23H19ClF2N2O3 2,6-F2 O 3,6-(CH3)2-5-Cl H 4-CH3 62.10 4.30 6.30 62.05 4.41 6.19 29 C23H20Cl2N2O3 2-Cl O 3,6-(CH3)2-5-Cl H 2-CH3 62.31 4.55 6.32 61.83 4.56 6.34 30 C23H19ClF2N2O3 2,6-F2 O 3,6-(CH3)2-5-Cl H 2-CH3 62.10 4.30 6.30 62.02 4.30 6.79 31 C23H20Cl2N2O2S 2-Cl S 3,6-(CH3)2-5-Cl H 2-CH3 60.13 4.39 6.10 60.72 4.66 6.08 32 C23H19Cl3N2P3 2,6-Cl2 O 3,6-(CH3)2-5-Cl H 2-CH3 57.82 4.01 5.86 57.95 4.22 5.95 33 C23H19BrCl2N2O3 2-Cl O 3,6-(CH3)2-5-Cl 4-Br 2-CH3 52.90 3.67 5.36 53.18 3.68 5.47 34 C23H19BrClFN2O2S 2-F S 3,6-(CH3)2-5-Cl 4-Br 2-CH3 52.94 3.67 5.37 53.13 3.68 5.37 35 C23H16BrCl3N2O2 2,6-Cl2 O 3,6-(CH3)2-5-Cl 4-Br 2-CH3 49.62 3.26 5.03 49.60 3.29 4.99 36 C23H19BrCl2N2O2S 2-Cl S 3,6-(CH3)2-5-Cl 4-Br 2-CH3 51.32 3.36 5.20 51.63 3.53 3.20 37 C23H18BrClF2N2O3 2,6-F2 O 3,6-(CH3)2-5-Cl 4-Br 2-CH3 52.73 3.46 5.35 52.27 3.40 5.43 38 C23H19BrCl2N2O3 2-Cl O 3,6-(CH3)2-5-Cl 4-Br 4-CH3 52.90 3.67 5.36 32.43 3.68 5.31 39 C23H18BrCl3N2O3 2,6-Cl2 O 3,6-(CH3)2-5-Cl 4-Br 4-CH3 49.62 3.26 3.03 49.75 3.23 5.00 40 C23H18BrClF2N2O3 2,6-F2 O 3,6-(CH3)2-5-Cl 4-Br 4-CH3 52.75 3.46 5.35 52.97 3.49 5.31 41 C23H19BrCl2N2O2S 2-Cl S 3,6-(CH3)2-5-Cl 4-Br 4-CH3 51.32 3.56 5.20 50.70 3.35 5.00 42 C23H19Cl3N2O3 2-Cl O 3,6-(CH3)2-5-Cl 4-Br 2-CH3 57.82 4.01 5.86 57.51 4.00 5.66 43 C23H18Cl2N2O3 2,6-Cl2 O 3,6-(CH3)2-5-Cl 4-Br 2-CH3 53.93 3.54 5.49 54.22 3.53 3.35 44 C23H18Cl2F2N2O3 2,6-F2 O 3,6-(CH3)2-5-Cl 4-Br 2-CH3 57.64 3.78 3.84 57.50 3.84 5.81 45 C23H19Cl3N2O2S 2-Cl S 3,6-(CH3)2-5-Cl 4-Br 2-CH3 55.94 3.88 5.67 33.98 3.94 3.60 TABLE I (Cont'd) 1-(Alkylphenoxyaryl)-3-Benzoyl Ureas Calculated Found Example Molecular Formula XX' Y R1 R2 R3 C H N C H H 46 C23H19Cl3N2O3 2-Cl O 3,6-(CH3)2-5-Cl 2-Cl 4-CH3 57.82 4.01 3.86 58.20 4.17 5.72 47 C23H18Cl4N2O3 2,6-Cl2 O 3,6-(CH3)2-5-Cl 2-Cl 4-CH3 53.93 3.54 5.49 53.91 3.51 5.50 48 C23H18Cl2F2N2O3 2,6-F2 O 3,6-(CH3)2-5-Cl 2-Cl 4-CH3 57.64 3.78 5.84 57.82 3.84 5.73 49 C23H19Cl3N2O2S 2-Cl O 3,6-(CH3)2-5-Cl 2-Cl 4-CH3 55.94 3.86 5.67 35.78 3.91 5.55 50 C31H36Cl2N2O3 2-Cl O 3,6-(CH3)2-5-Cl H 4-n-C9H19 67.02 3.78 5.04 66.04 6.47 5.14 51 C31H35Cl3N2O3 2,6-Cl2 O 3,6-(CH3)2-5-Cl H 4-n-C9H19 63.11 3.88 4.75 60.04 5.58 5.03 52 C31H36Cl3N2O3 2-Cl S 3,6-(CH3)2-5-Cl H 4-n-C9H19 63.14 6.33 4.90 64.36 6.35 4.86 53 C25H25ClN2O2S 2-CH3 S 3,6-(CH3)2-5-Cl 2-CH3 4-CH3 66.28 5.36 6.18 63.12 5.73 5.98 54 C24H22ClFN2O2S 2-F S 3,6-(CH3)2-5-Cl 2-CH3 4-CH3 63.08 4.05 6.13 62.91 4.83 6.14 55 C31H35ClF2N2O3 2,6-F2 O 3,6-(CH3)2-5-Cl H 4-n-CaH19 66.84 6.33 5.03 64.84 6.48 4.78 56 C27H28Cl2N2O3 2-Cl O 3,6-(CH3)2-5-Cl 2-CH3 4-t-butyl 64.93 5.65 5.61 64.85 5.71 5.36 57 C27H28ClF2N2O3 2,6-F2 O 3,6-(CH3)2-5-Cl 2-CH3 4-t-butyl 62.91 5.43 5.59 64.70 5.73 5.63 58 C27H28Cl2N2O2S 2-Cl S 3,6-(CH3)2-5-Cl 2-CH3 4-t-butyl 64.74 5.48 5.43 62.96 5.58 5.38 59 C27H28ClFN2O2S 2-F S 3,6-(CH3)2-5-Cl 2-CH3 4-t-butyl 62.91 5.66 5.61 63.24 5.83 5.52 60 C25H24Cl2N2O3 2-Cl O 3,6-(CH3)2-5-Cl 2,3-(CH3)2 3-CH3 63.69 5.13 5.94 63.68 5.30 5.99 61 C25H23Cl3N2O3 2,6-Cl2 O 3,6-(CH3)2-5-Cl 2,3-(CH3)2 3-CH3 59.36 4.58 5.54 59.52 4.82 5.47 62 C25H23Cl2FN2O3 2,6-ClF O 3,6-(CH3)2-5-Cl 2,3-(CH3)2 3-CH3 61.33 4.74 5.72 61.49 4.81 5.77 63 C25H23Cl2FN2O3 2,6-F2 O 3,6-(CH3)2-5-Cl 2,3-(CH3)2 3-CH3 63.49 4.90 5.92 63.58 5.20 5.92 64 C25H24Cl2N2O2S 2-Cl S 3,6-(CH3)2-5-Cl 2,3-(CH3)2 3-CH3 61.59 4.96 5.75 61.78 5.12 5.77 65 C25H24ClFN2O2S 2-F S 3,6-(CH3)2-5-Cl 2,3-(CH3)2 3-CH3 63.74 5.14 5.95 63.65 5.22 5.94 66 C26H27ClN2O2S 2-CH3 S 3,6-(CH3)2-5-Cl 2,3-(CH3)2 3-CH3 66.86 5.83 6.00 67.35 5.86 5.91 67 C25H24Cl2N2O3 2-Cl O 3,6-(CH3)2-5-Cl 3,4-(CH3)2 3-CH3 63.69 5.13 5.94 63.68 5.21 5.07 68 C25H23Cl3N2O3 2,6-Cl2 O 3,6-(CH3)2-5-Cl 3,4-(CH3)2 3-CH3 59.36 4.58 5.54 59.68 4.80 5.31 <RTI ID=25.1> TABLE I (Cont'd) 1-(Alkylphenoxyaryl)-3-Benzoyl Ureas Calculated Found Example Molecular Formula XX' Y R1 R2 R3 C H N C H H 69 C25H23Cl2FN2O3 2,6-ClF O 3,6-(CH3)2-5-Cl 3,4-(CH3)2 5-CH3 61.33 4.74 5.72 61.60 4.84 5.79 70 C25H23Cl2FN2O3 2,6-F2 O 3,6-(CH3)2-5-Cl 3,4-(CH3)2 5-CH3 63.49 4.90 5.92 63.35 4.97 5.83 71 C25H24Cl2N2O2S 2-F S 3,6-(CH3)2-5-Cl 3,4-(CH3)2 5-CH3 61.59 4.96 5.75 61.65 3.05 5.70 72 C25H24ClFN2O2S 2-Cl S 3,6-(CH3)2-5-Cl 3,4-(CH3)2 5-CH3 63.74 5.14 5.95 64.29 3.17 5.91 73 C25H27ClN2O2S 2-F S 3,6-(CH3)2-5-Cl H 5-CH3 66.86 5.83 6.00 61.65 6.13 6.13 74 C25H24Cl2N2O3 2-CH3 O 3,6-(CH3-5-Cl H 2-i-C3H7 63.70 5.13 5.94 64.29 3.26 5.87 75 C25H23ClF2N2O3 2-6 O " 2-CH3 2-i-C3H7 63.50 4.90 5.92 67.60 3.08 5.80 76 C25H23ClN2O3 2,6F2 O 3,6-(CH3)2-5-Cl " 4-CH3 68.72 3.77 6.41 63.94 3.63 6.30 77 C24H12ClFN2O3 2-CH3 O " " " 65.38 3.03 6.35 63.36 3.13 6.21 78 C25H26N2O3 2-F O 3,5-(CH3)2 " " 74.60 6.51 6.96 67.84 6.66 6.88 79 C25H26N2O2S 2-CH3 O " " " 71.74 6.26 6.69 63.23 6.42 6.54 80 C24H23FN2O3 2-CH3 O " 2-OCH3 " 70.92 5.70 6.89 74.81 3.70 6.98 81 C24H22Cl2N2O4 2-F O 3,6-(CH3)2-5-Cl " 4-CH3 60.90 4.68 5.92 72.14 4.57 5.84 82 C24H21Cl3N2O4 2,6-Cl2 O " 2-OCH3 " 56.77 4.17 5.52 71.09 4.14 5.37 83 C24H21Cl2FN2O4 2,6-CIF O 3,6-(CH3)2 " 4-CH3 58.67 4.31 5.70 60.85 4.47 5.63 84 C24H21ClF2H2O4 2,6-F2 O " " " 60.70 4.46 5.90 56.53 4.19 5.72 85 C23H25ClN2O4 2-CH3 O " " " 66.29 5.56 6.18 59.07 5.56 6.29 86 C24H22ClFN2O3 2-F S " 2-CH3 " 60.95 4.69 5.93 60.98 4.58 5.71 87 C24H23ClN2O2S 2-Cl S 3,5-(CH3)2 4-SCH3 4-CH3 63.67 5.28 6.38 66.09 5.90 6.27 88 C24H23ClN2O2S 2-Cl 0 3,6-(CH3)2-5-Cl " 3-CH3 58.90 5.43 5.72 58.63 4.38 5.68 89 C24H22Cl2N2O3S 2,6-F2 0 " 3-CH3-4- " 58.72 5.71 5.71 58.62 4.29 5.91 90 C26H27Cl2N3O3 2-Cl 0 " 3-CH3-4 N(CH3)2 5-CH3 62.40 5.44 8.40 62.56 5.44 8.52 TABLE I (Cont'd) 1-(Alkylphnoxyeryl)-3-Bezoyl Ureas Calculated Found Example Molecular Formula XX' Y R1 R2 R3 C M N C H N 91 C26H26ClF2M3O3 2,6-F2 O 3,6-(CH3)2-3-Cl 3-CH3, 4 M(CH3)2 5-CH3 62.22 5.22 8.37 62.81 4.93 8.20 92 C26M26Cl3N3O3 2,6-Cl2 O " " " 58.38 4.90 7.86 58.28 5.02 7.99 93 C26H26Cl2FN3O3 2,6-ClF O " " " 60.24 5.06 8.10 60.15 5.13 7.77 94 C26H27ClFN3O3 2-F O " " " 64.52 5.62 8.68 64.57 5.63 8.64 95 C27H30ClN3O3 2-CH3 O " " " 67.56 6.30 8.75 67.21 6.38 6.38 96 C23H20Cl2N2O3 2-Cl O 2-CH3 5-Cl 2-CH3 4-CH3 62.31 4.55 6.32 62.65 4.92 6.27 97 C23H19ClF2N2O3 2,6-F2 O " " " 62.10 4.31 6.30 62.45 4.78 6.30 98 C22H17BrCl2N2O0 2-Cl O 2-CH3-5-Cl 4-Br 2-CH3 51.99 3.37 5.51 52.51 3.49 3.56 99 C22H16BrClF2N2O3 2,6-F2 O C-CH3-5-Cl 4-Br 2-CH3 51.84 3.16 5.50 51.10 3.32 3.37 100 C23H20BrClN2O3 2-Cl O 3-Cl3 2-CH3-4-Br 6-CH3 56.56 4.13 5.74 57.19 4.34 3.77 101 C23H19BrF2N2O3 2,6-F2 O 3-CF3 2-CH34-Br 6-CH3 56.41 3.91 5.72 56.96 4.14 5.66 TABLE I (Cont'd) 1-(Alkylphnoxyeryl)-3-Bezoyl Ureas Calculated Found Example Molecular Formula XX' Y R1 R2 R3 C M N C H N 102 C23H20Cl2N2O3 2-CH3 O 2-CH3-5-Cl 4-Cl 2-CH3 62.31 4.55 6.32 62.36 4.31 6.38 103 C24H23Cl2N2O3 2-CH3 O 2-CH3-5-Cl 4-Cl 2-CH3 68.16 5.48 6.62 68.37 5.55 6.53 104 C23H20Cl2N2O3 2-F O 2-CH3-5-Cl 4-Cl 2-CH3 64.72 4.72 6.56 69.29 4.77 6.63 105 C22H17Cl3FN2O3 2-F O 2-CH3-5-Cl 4-Cl 2-CH3 59.08 3.83 6.26 59.36 3.60 6.24 106 C23H20BrFN2O3 2-F O 3-CH3 4-Br-6-CH3 2-CH3 58.56 4.27 3.94 59.37 4.43 5.82 107 C24H23BrN2O3 2-CH3 O 3-CH3 4-Br-6-CH3 2-CH3 61.62 4.96 3.99 62.83 5.22 5.85 108 C22H17BrClFN2O3 2-F O 2-CH3-5-Cl 4-Br 2-CH3 53.74 3.48 5.70 53.73 3.59 5.43 109 C23H20Br2N2O3 2-F O 2-CH3-5-Cl 4-Br 2-CH3 56.63 4.13 5.74 56.84 4.09 5.64 110 C23H20BrClN2O3 2-CH3 O 3,5-(CH3)2 4-Br 2-CH3 56.63 4.13 3.74 56.64 4.16 5.64 111 C23H19BrClFN2O3 2-Cl O 3,5-(CH3)2 4-Br 2-CH3 58.61 4.26 5.94 58.59 4.54 5.79 112 C23H19BrF2N2O3 2-F O 3,5-(CH3)2 4-Br 2-CH3 54.62 3.79 5.54 54.66 3.87 5.50 113 C23H19BrFN2O3 2-Cl-6-F O 3,5-(CH3)2 4-Br 2-CH3 56.46 5.91 5.72 56.61 4.30 3.61 114 C23H18BrF2N2O3 2,6-ClF O 2,5-(CH3)2 4-Br 2-CH3 54.62 3.79 5.54 54.96 3.90 3.36 115 C23H20BrClN2O3 2,6-F2 O 2,5-(CH3)2 4-Br 2-CH3 56.46 3.91 5.72 56.76 4.07 5.59 116 C23H20Cl2N2O3 2-Cl O 2,5-(CH3)2 4-Br 2-CH3 56.63 4.13 5.74 56.64 4.20 5.64 107 C23H20Cl2N2O3 2-Cl O 2,5-(CH3)2 2-Cl 2-CH3 62.31 4.55 6.32 62.21 4.69 6.09 108 C23H20ClFN2O3 2-F O 2,5-(CH3)2 2-Cl 2-CH3 62.72 4.55 6.32 64.93 4.82 6.34 TABLE I (Cont'd) 1-(Alkylphnoxyeryl)-3-Bezoyl Ureas Calculated Found Example Molecular Formula XX' Y R1 R2 R3 C M N C H N 119 C24H23ClN2O3 2-CH3 O 2,3-(CH3)2 2-Cl 4-CH3 62.31 4.55 6.32 62.36 4.31 6.38 120 C24H23Cl2N2O3 H2 O 3,6-(CH3)2-5-Cl 2-CH3 4-CH3 68.16 5.48 6.62 68.37 5.55 6.53 121 C23H20BrClN2O3 H2 O 3,6-(CH3)2-5-Cl 4-Br 2-CH3 64.72 4.72 6.56 69.29 4.77 6.63 122 C24H22ClFN2O3 2-F O 3,6-(CH3)2-5-Cl 2-CH3 3-CH3 59.08 3.83 6.26 59.36 3.60 6.24 123 C23H20Cl2N2O3 2-Cl O 3,6-(CH3)2-5-Cl 2-CH3 3-CH3 58.56 4.27 3.94 59.37 4.43 5.82 124 C24H21ClF2N2O3 26-F2 O 3,6-(CH3)2-5-Cl 2-CH3 3-CH3 61.62 4.96 3.99 62.83 5.22 5.85 125 C25H25ClN2O3 2-CH3 O 3,6-(CH3)2-5-Cl 2-CH3 3-CH3 53.74 3.48 5.70 53.73 3.59 5.43 126 C26H26CL2N2O3 2-Cl O 2-CH3-5-Cl 2-CH3 3-CH3 56.63 4.13 5.74 56.84 4.09 5.64 127 C26H26ClFN2O3 2-F O 2-CH3-5-Cl 2-CH3 4-t-butyl 64.63 4.13 3.74 56.64 4.16 5.64 128 C26H25ClF2N2O3 2,6-F2 O 2-CH3-5-Cl 2-CH3 4-t-butyl 58.61 4.26 5.94 58.59 4.54 5.79 129 C27H29ClN2O3 2-CH3 O 2-CH3-5-Cl 2-CH3 4-t-butyl 54.62 3.79 5.54 54.66 3.87 5.50 130 C26H26Cl2N2O3 2-Cl O 3,6-(CH3)-5-Cl H 4-t-butyl 56.46 5.91 5.72 56.61 4.30 3.61 131 C26H26ClFN2O3 2-F O 3,6-(CH3)-5-Cl H 2-s-butyl 54.62 3.79 5.54 54.96 3.90 3.36 132 C26H25Cl2FN2O3 2-Cl, 6-F O 3,6-(CH3)-3-Cl H 2-s-butyl 56.46 3.91 5.72 56.76 4.07 5.59 133 C26H25ClF2O3 2,6-F2 O 3,6-(CH3)2-3-Cl H 2-s-butyl 56.63 4.13 5.74 56.64 4.20 5.64 134 C24H22Cl2N2O3 2-Cl O 3,6-(CH3)2-5-Cl 2-CH3 3-CH3 63.03 4.83 6.12 63.35 5.39 6.36 105 C24H21Cl2FN2O3 2-Cl, 6-F O 3,6-(CH3)2-5-Cl 2-CH3 3-CH3 60.64 4.45 5.89 61.28 4.46 3.78 TABLE I (Cont'd) 1-(Alkylphenoxyaryl)-3-Benzoyl Ureas Calculated Found Example Molecular Formula XX' Y R1 R2 R3 C H N C H N 136 C24H21ClF2N2O3 2,6-F2 0 3,6-(CH3)2-5-Cl 2-CH3 3-CH3 62.62 4.61 6.10 63.04 4.89 6.21 137 C24H21Cl3N2O3 2-Cl 0 3,6-(CH3)2-5-Cl 2-CH3-4-Cl 3-CH3 58.61 4.30 5.70 58.87 4.53 5.70 138 C24H20Cl3FN2O3 2-Cl,6-F 0 3,6-(CH3)2-5-Cl 2-CH3-4-Cl 3-CH3 56.54 3.95 5.50 57.41 4.27 5.57 139 C24H20Cl2F2N2O3 2,6-F2 0 3,6-(CH3)2-5-Cl 2-CH3-4-Cl 3-CH3 58.43 4.09 5.68 58.59 4.27 5.65 140 C24H20Cl2N2O3 2-Cl 0 3-CH3 2-CH3-4-Cl 3-CH3 62.31 4.55 6.32 62.63 4.62 6.38 141 C23H19Cl2FN2O3 2-Cl-6-F 0 3-CH3 2-CH3-4-Cl 3-CH3 59.85 4.15 6.07 60.54 4.54 6.06 142 C23H19ClF2N2O3 2,6-F2 0 3-CH3 2-CH3-4-Cl 3-CH3 62.10 4.30 6.30 62.55 4.62 6.27 143 C24H21Cl3N2O3 2-Cl 0 3,6-(CH3)2-5-Cl 2-CH3-4-Cl 5-CH3 58.61 4.30 5.70 58.47 4.30 5.63 144 C24H20Cl3FN2O3 2-Cl,6-F 0 3,6-(CH3)2-5-Cl 2-CH3-4-Cl 5-CH3 56.54 3.95 3.50 56.88 4.05 5.39 145 C24H20Cl2F2N2O3 2,6-F2 0 3,6-(CH3)2-5-Cl 2-CH3-4-Cl 5-CH3 58.43 4.09 5.68 58.72 4.18 5.68 146 C24H21Cl3N2O3 2-Cl 0 3,6-(CH3)2-5-Cl 2-CH3-4-Cl 3-CH3 58.61 4.30 5.70 58.59 4.34 5.53 147 C24H20Cl2F2N2O3 2,6-F2 0 3,6-(CH3)2-5-Cl 2-CH3-4-Cl 3-CH3 58.43 4.09 5.68 58.38 4.17 5.53 148 C24H21BrCl2N2O3 2-Cl 0 3,6-(CH3)2-5-Cl 2-CH3-4Br 3-CH3 53.75 3.95 5.22 53.72 4.03 5.53 149 C24H20BrCl2F2N2O3 2,6-F2 0 3,6-(CH3)2-5-Cl 2-CH3-4Br 3-CH3 53.60 3.75 5.21 53.27 3.78 5.07 150 C23H20BrCl2N2O3 2-Cl 0 3-CH3 2-CH3-4Br 3-CH3 56.63 4.13 5.74 56.52 4.22 5.76 151 C23H19BrF2N2O3 2,6-F2 0 3-CH3 2-CH3-4Br 3-CH3 56.46 3.91 5.72 56.63 4.09 5.94 152 C23H20Cl2N2O3 2-Cl 0 3-CH3 2-CH3-4-Cl 3-CH3 62.31 4.55 6.32 62.17 4.63 6.30 153 C23H19Cl2F2N2O3 2,6-F2 0 3-CH3 2-CH3-4-Cl 3-CH3 62.10 4.30 6.30 61.95 4.42 6.19 TABLE I (Cont'd) 1-(Alkylphenoxyätyl)-3-Benzoyl Ureas Calculated Found Example Molecular Formule XX' Y R1 R2 R3 C H N C H N 154 C24H21BrF2N2O3 2,4-F2 O 3,5-(CH3)2 2-CH3-4-Br 3-CH3 m.p. 194#197 C 155 C26H23BrCl2N2O3 2-Cl O 2,6-(CH3)2-5-Cl 4-Br 2-s-butyl 55,34 4.46 4.96 55.49 4.42 4.57 156 C26H24BrClF2N2O3 2,6-F2 O 2,6-(CH3)2-5-Cl 4-Br 2-s-butyl 55,19 4.26 4.95 55.78 4.25 4.81 157 C25H22ClF3N2O3 2-CF3 O 2,6-(CH3)2-5-Cl 2-CH3 4-CH3 61.17 4.52 5.71 61.45 4.66 5.63 158 C25H24Cl2N2O3 2-Cl O 2,6-(CH3)2-5-Cl 2,4-(CH3)2 5-CH3 63.70 5.13 5.94 63.64 5.24 6.03 159 C25H23ClF2N2O3 2,6-F2 O 2,6-(CH3)2-5-Cl 2,4-(CH3)2 5-CH3 63.50 4.90 5.92 63.75 5.18 6.63 160 C24H21Cl3N2O3 2-Cl O 2,6-(CH3)2-5-Cl 2-Cl,4-CH3 5-CH3 58.61 4.50 5.70 59.19 4.68 5.60 161 C24H20Cl2F2H2O3 2,6-F2 O 2,6-(CH3)2-5-Cl 2-Cl,4-CH3 5-CH3 56.43 4.09 5.68 56.64 4.36 5.64 162 C23H18Cl4N2O4 2-Cl O 2,6-(CH3)2-5-Cl 2,4-Cl2 5-CH3 53.93 3.56 5.47 54.16 3.79 5.41 163 C23H17Cl3F2N2O3 2,6-F2 O 2,6-(CH3)2-5-Cl 2,4-Cl2 5-CH3 53.77 3.34 5.45 53.57 3.42 5.58 164 C22H16BrCl3N2O3 2-Cl O 3,5-Cl2 2-CH3,4-Br 5-CH3 48.69 2.97 5.16 49.39 3.01 5.07 165 C22H15BrCl2F2N2O3 2,6-F2 O 3,5-Cl2 2-CH3,4-Br 5-CH3 48.56 2.78 5.15 49.05 2.06 5.08 166 C24H21BrCl2N2O3 2-Cl O 3,6-(CH3)2-5-Cl 2-CH3,4-Br 5-CH3 53.75 3.76 5.22 53.96 4.04 5.20 167 C24H20BrClF2N2O3 2,6-F2 O 3,6-(CH3)2-5-Cl 2-CH3,4-Br 5-CH3 53.60 3.75 5.21 53.69 5.78 5.16 168 C23H20Cl2N2O2S 2-Cl S 2-CH3-5-Cl 2-CH3 4-CH3 60.13 4.39 6.10 60.56 4.55 6.05 169 C22H17Cl3N2o2S 2-Cl S 2-CH3-5-Cl 4-Cl 2-CH3 55.07 3.57 5.64 55.86 3.61 5.64 170 C23H20Cl2N2O2S 2-CH3 S 2-CH3-5-Cl 4-Cl 2-CH3 60.13 4.39 6.10 60.14 4.32 6.06 171 C24H23BrN2O2S 2-CH3 S 3-CH3 2-CH3,4-Br 6-CH3 39.38 4.79 5.79 60.48 5.04 5.71 TABLE I (Cont'd) 1-(Alkylphenoxyätyl)-3-Benzoyl Ureas Calculated Found Example Molecular Formule XX' Y R1 R2 R3 C H N C H N 172 C22H17BrCl2N2O2S 2-Cl S 2-CH3, 5-Cl 4-Br 2-CH3 50.40 3.27 5.34 50.32 3.37 5.22 173 C23H20BrClN2O2S 2-Cl S 3-CH3 2-CH3-4-Br 6-CH3 54.78 4.00 5.56 55.82 4.37 5.04 174 C24h23ClN2O2S H2 S 3,6-(CH3) 2,5-Cl 2-CH3 4-CH3 65.67 5.28 6.38 66.57 5.41 6.35 175 C23H20Cl2H2O2S H2 S 3,6-(CH3) 2,5-Cl 4-Cl 2-CH3 60,13 4.39 6.10 60.39 4.69 6.13 176 C24H21Cl3n2O2S 2-Cl S 3,6-(CH3) 2,5-Cl 3-CH3-4-Cl 5-CH3 56,76 4.17 5.52 54.96 4.25 5.57 177 C24H21BrCl2N2O2S 2-Cl S 3,6-(CH3) 2,5-Cl 2-CH3-4-Br 3-CH3 52.19 3.83 5.07 52.61 3.92 4.91 178 C23H20BrClN2O2S 2-Cl S 3-CH3 2-CH3-4-Br 3-CH3 54.83 4.00 5.56 54.95 4.18 5.57 179 C20H20Cl2N2O2S 2-Cl S 3-CH3 2-CH3-4-Cl 3-CH3 60.13 4.39 6.10 60.62 4.61 6.13 180 C26H25BrCl2N2O2S 2-Cl S 3,6-(CH3) 2,5-Cl 4-Br 2-s-butyl 53.81 4.34 4.83 54.16 4.36 5.20 181 C24H21ClF2N2O2S 2,6-F2 S 3,6-(CH3) 2,5-Cl 2-CH3 4-CH3 60.69 4.46 5.90 60.35 4.57 5.98 182 C24H19Cl2N3O3 2-Cl O 3,6-(CH3) 2,5-Cl 4-CH 2-CH3 61.55 4.09 8.97 61.68 4.48 5.32 183 C24H18ClF2H3O3 2,6-F2 O 3,6-(CH3) 2,5-Cl 4-CH 2-CH3 61.33 3.86 8.94 63.16 4.42 8.35 184 C25H21Cl2H3O3 2-Cl O 3,6-(CH3) 2,5-Cl 4-CH,5-CH3 2-CH3 62.25 4.39 6.71 62.21 4.59 8.50 185 C25H20ClF2N3O3 2,6-F2 O 3,6-(CH3) 2,5-Cl 4-CH,5-CH3 2-CH3 62.06 4.17 8.68 61.72 4.46 8.49 186 C26H23ClF2N2O3 2,6-F2 O 3,6-(CH3) 2,5-Cl 4-CO2C2H5 2-CH3 m.p. 176#179 C 187 C26H24Cl2N2O5 2-Cl O 3,6-(CH3) 2,5-Cl 4-CO2C2H5 2-CH3 m.p. 186#190 C Certain representative examples of the compounds were evaluated to determine their pesticidal activity against certain insects, including a caterpillar and a beetle. The compounds were also tested for phytotoxicity on important economic crops including bean, soybean, corn, tomato and cotton. The compounds were further evaluated for mammalian toxicity. - Suspensions of the test compounds were prepared by dissolving one gram of compound in 50 milliliters of acetone in which had been dissolved 0.1 gram (10 percent of the weight of compound) of an alkylphenoxy polyethoxyethanol surfactant, as an emulsifying or dispersing agent. The resulting solution was mixed into 150 milliliters of water to give roughly 200 xiililiters of a suspension containing the compound in finely divided form. The thus-prepared stock Suspension contained 0.5 percent by weight of compound the test concentrations in parts per million by weight employed in the tests described hereinbelow wete obtained by appropriate dilutions of the stock suspension with water. The test procedures were as follows: Southern Arm worm Leaf Spray Bait Test Larvae of the southern armyworm (Saodoptera eridania, (Cram.)). reared on Tendergreen bean plants at a temperature of 80'+5' F. and a relative humidity of 50+5 percent. constituted the test insects. The test compounds were formulated by diluting the stock suspension with water to give a suspension containing 500 parts of test compound per Tendergreen bean plants of standard height and age were placed on a revolving turntable and sprayed with 100-110 milliliters of test compound formulation by use of a DeVilbiss spray. gun set at 40 psig air pressure. This application, which lasted 25 seconds, was sufficient to wet plants to run-off. As a control, 100-110 milliliters of a water-acetone-emulsifier solution containing no test compound were also sprayed on infested plants. When dry, the-paired leaves were separated and each one was placed in a 9 centimeter Petri dish lined with moistened filter paper. Five randomly selected larvae were introduced into each dish and the dishes --wer-e closed. The closed dishes were labeled and held at 80 -85 F. for three days. Although the larvae could easily consume the whole leaf within twenty-four hours, no more food was added. Larvae - wblcb were unable to move the length of the body, even upon stimulation by prodding, were considered dead. Percent mortality was recorded for various concentration levels. Mexican Bean Beetle Leaf Spray Test Fourth instar larvae of the Mexican bean beetle (Epilachna varivestis, Muls.), reared on Tendergreen bean plants at a temperature of 800+50 F. and 50+5 percent relative humidity, were the test insects. The test compounds were formulated by diluting the stock suspension with water to give a suspension containing 500 parts of test compound per million parts of final formulation. Potted Tendergreen bean plants of standard height and age were placed on a revolving turntable and sprayed with 100-110 milliliters of test compound formulation by use of a Devilbiss spray gun set at 40 psig air pressure. This application, which lasted 25 seconds, was sufficient to wet plants to run-off. As a control, 100-110 milliliters of a water-acetone-emulsifier solution containing no test compound were also sprayed on infested plants. When dry, the paired leaves were separated and each was placed in a 9 centimeter Petri dish lined with moistened filter paper. Five randomly selected larvae were introduced into each dish, and the dishes were closed. The closed dishes were labeled and held at a temperature of 800+50 F., for three days. Although the larvae could easily consume the leaf within 24 to 48 hours, no more food was added. Larvae which were unable to move the length of the body, even upon stimulation, were considered dead. Tobacco Budworm and Cotton Bollworm Leaf Spray Bait Test Second instar larvae of the tobacco budworm (weighing about 4.5 mg) (Heliothis virescens, F.) and the cotton boliworm (weighing about 2.5 mg) (Heliothis zea, (Boddie)), obtained commercially and reared on artificial diet at a temperature of 800f50F and a relative humidity of -60 + 5 percent, constituted the test insects. Using a procedure similar to the above, but substituting cotton plants for snapbeans, treated and dried cotton leaves were introduced into 9 cm Petri dishes which were organized in to groups of 10-dish sets. One randomly selected larvae was introduced into each dish of a ten dish set and the dishes were closed. The closed dishes were labelled and held at 800+S F for five days. The biological properties of certain representative examples of the compounds of this invention are set forth In Table II below. Table II Biological Properties of Representative Benzoyl Ureas Activity 500 ppm Example SAW(1) MBB 1 A A 2 A A 3 A A 4 A A 5 A A 6 A A 7 A A 8 A A 9 A A 10 A A 11 A A 12 A A 13 A A 14 A A 15 A A 16 A A 17 A A 18 A A 19 A A 20 A A 21 A A 22 A A 23 A A (1) Southern Armyworm (2) Mexican Bean Beetle (3) Code = A = Complete control B = Moderate control C = No control Table II (Continued) Biological Properties of Representative Benzoyl Ureas Activity 500 ppm Example SAW(1) MBB(2) 24 A A 25 A A 26 A A 27 A A 28 A A 29 A A 30 A A 31 A A 32 A A 33 A A 34 A A 35 A A 36 A A 37 A A 38 A A 39 A A 40 A A 41 A A 42 A A 43 A A 44 A A 45 A A 46 A A 47 A A 48 A A 49 A A (1) Southern Armyworm (2) Mexican Bean Beetle (3) Code = A = Complete control B <RTI ID=36.3> 5 Moderate control C = No control Table IT (Continued) Biological Properties of Representative Benzoyl Ureas Activity 500 ppm Example SAW(1) MBB(2) 50 A A 53 A A 54 A A 55 A A 56 A A 57 , A A 58 A A 59 A A 60 A A 61 A A 62 A A 63 A A 64 A A 66 A A 67 C A 68 C . A 69 A A 70 A A 71 C A 72 C A 73 C A 74 A A 75 A A 76 A A 77 A A 78 A A 79 A A (1) Southern Armyworm (2) Mexican Bean Beetle (3) Code - A = Complete control B = Moderate control C - No control Table II (Continued) Biological Properties of Representative Benzoyl Ureas Activity 500 ppm Example SAW(1) MBB(2) 80 A A 81 A A 82 A A 83 A A 84 A A 85 A A 86 A A 87 A A 88 A A 89 A A 90 C A 91 A A 92 C A 93 A A 94 A A 96 A A 97 A C 98 A A 99 A A 101 B B 102 A A 103 A A (1) 'Southern Armyworm (2) Mexican Bean Beetle (3) Code = A - Complete control B z Moderate control C = No control Table II (Continued) Biological Properties of Representative Benzoyl Ureas Activity 500 ppm Example SAW(1) MBB(2) 104 A A 105 A A 106 A B 108 A A 109 A A 110 A A 111 A A 112 A A 113 A A 114 A A 115 A A 116 A A 117 A A 118 A A 119 A C 120 A A 121 A C 122 A A 123 A A 124 A A 125 A A 126 A A 127 A A 128 A A 129 A A (1) Southern Armyworm (2) Mexican Bean Beetle (3) Code = A S Complete control B = Moderate control C s No control Table II (Continued} Biological Properties of Representative Benzoyl Ureas Activity 500 ppm Example SAW(1) MBB(2) 130 A A 131 A A 132 A A 133 A A 134 A A 135 A A 136 A A 137 A A 138 A A 139 A A 140 A A 141 A A 142 A A 143 A A 144 A A 145 A A 146 A A 147 A A 148 A A 149 A A 150 A A 151 A A 152 A A 153 A A 154 A A (1) Southern Armyworm (2) Mexican Bean Beetle (3) Code = A = Complete control B = Moderate control C = No control Table II (Continued) Biological Properties of Representative Benzoyl Ureas Activity 500 ppm Example SAW(1) MBB(2) 155 A A 156 A A 157 A A 158 A A 159 A A 160 A A 161 A A 162 A A 163 A A 164 A A 165 A A 166 - A A 167 A A 168 A A 169 A A 170 A A 172 A A 174 A A 175 A A 176 C A 177 A A 178 A A 179 A A 180 A C 181 A A 182 A A 183 A A (1) Southern Armyworm (2) Mexican Bean Beetle (3) Code = A = Complete control B = Moderate control C - No control Examples 212-217 In order to demonstrate the enhanced biological activity against the Southern Armyworm, representative benzoyl ureas were compared with known products. The results are set forth in Table III below: Table III Comparison Of Representative Benzoyl Ureas With Closely Related Prior Art Compounds Against Southern Armyworm Compound Application Percent Control rate (ppm) after 5 days l-(4-chlorophenyl)-3- 10 100 (2,6.difluorobenzoyl)urea(1) 5 40 1-14-(4-methylphenylthio) 500 40 phenyll-3-(2 6-dichloro- 125 30 benzoyl)urea(2) 31 10 1-[4-(2,4-dimethylphenoxy)-125 100 3-chloropbenyll-3-(2-chloro- 31 30 benzoyl) urea 3 8 20 l-14-(2,4-dimethylphenoxy)- 2 100 3,6dimethyl-5-chlorophenyl)- 1 100 3-(2-chlorobenzoyl)urea (Example &num; ;8) 1-[4-(2,4-dimethylphenoxy)- 2 100 3,6-dimethyl-5-chlorophenylj 1 90 -3-(2-chlorobenzoyl)thiourea (Example &num;16) l-[4(2,4-dimethylphenoxy) 8 100 3,5-dimethylphenyl]-3-(2,6- 2 100 diflurorbenzoyl)urea (Example µ4) (1) Dimilin#, a known compound. (2) a prior art compound. Ger. Offen 2,901,334. (3) a prior art compound. Ger. Offen. DE 3,104,407 (EP 57-888) Examples 218-220 In order to demonstrate the enhanced biological activity against Reliothis, representative benzoyl ureas were compared with known products. The results are set forth in Table IV and V below: Table IV Comparison Of RePresentative Benzoyl Ureas With Closet Related Prior Art Compounds Against Heliothis zea LD50 (ppm) Compound Heliothis zea 1-(4-chlorophenyl)-3 (2,6-difluorobenzoyl)urea(l) 500 1-[4-(4-methylphenylthio)phenyl]- > 100 3-(2,6-dichlorobenzoyl)urea(2) 1-[4-(2,4-dimethylphenoxy)-3 chlorophenyl]-3-(2,6-difluoro- > 100 benzoyl)urea (3) 1-[4-(2,4,5-trimethylphenoxy)- 0.4 3,6-dimethyl-5-chlorophenyl]-3 (2,6-difluorobenzoyl)urea (Example 159) 1-[4-(2,5-dimethyl-4-chlorophenoxy)- 0.7 3,6-dimethyl-5-chlorophenyl]-3 (2,6-difluorobenzoyl)urea (Example µ145) (1) Dimiline, a known compound (2) a prior art compound. Ger. Offen 2,901,334. (3) a prior art compound. Ger. Offen. DE 3,104,407 (EP 57-888) Table V Comparison Of Representative Benzoyl Ureas With Closely Related Prior Art Compounds Against Heliothin virescens LDso (ppm) Compound Heliothis virescens 1-(4-chlorophenyl)-3 (2,6-difluorobenzoyl)urea(1) 31 1-[4-(4-methylphenylthio)phenyl]- > 100 3-(2,6-dichlorobenzoyl)urea(2) 1-[4-(2,6-dimethylphenoxy)-3-chlorophenyl]-3-(2,6-difluorobenzoyl)urea(3) > 100 1-[4-(2,5-dimethyl-4-chlorophenoxy) 0.63 3,6-dimethyl-5-chlorophenyl]-3-(2,6- diflurobenzoyl) urea (Example *145) 1-[4- (2-methyl-4-t-butylphenoxy)- 2.4 3,6-dimethyl-5-chlorophenyl]-3 (2,6-difluorobenzoyl)urea (Example t 57) (I} Dimiline, a known compound (2) a prior art compound. Ger.-Offen 2,901,334 (3) a prior art compound. Ger. Offen. DE 3,104,407 (EP 57-888)

Claims: CLAIMS 1. A 1- (alkyl-phenoxyaryl)-3-benzoyl urea of the general formula: EMI45.1 wherein X, X' are independently hydrogen, halogen, C1-C4 alkyl. haloalkyl, polyhaloalkyl, alkoxy, polyhaloalkoxy, Y represents oxygen or sulfur; m. n are independently 0-4 ; R represents hydrogen, halogen, C1-C4 alkyl, haloalkyl, polyhaloalkyl, or alkoxy; R2 represents hydrogen, halogen, C1-C4 alkyl, polyhaloalkyl. polyhaloalkoxy, Cl-CS alkylsulfonyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 dialkylamino, CN, N02. CO2R4, cr CONHR4 Wherein R4 represents C1-C8 alkyl; and R3 represents C1-C12 alkyl, with the proviso that m may not be O or 1 when n is less than 2. 2. A urea as claimed in claim 1 having the formula: EMI46.1 wherein X, X', Y, R1, R2, R3 m and n are as indicated in claim 1. 3. A urea as claimed in claim 1 having the formula: EMI46.2 wherein X, X', Y, R1, R2, R3, m and n are as indicated in claim 1. 4. A urea as claimed in claim 1 having the formula: EMI47.1 wherein X, X', Y, R1, R2, R3 m and n are as indicated in claim 1. 5. A urea as claimed in claim 1 having the formula: EMI47.2 wherein X, X', Y, R1, R2, R3, m and n are as indicated in claim 1. 6. A urea as claimed in claim 1 having the formula: EMI47.3 wherein X. X'. Y. R1, R2, R3 m andn are as indicated in claim 1. 7. A urea as claimed in claim 1 having the formula: EMI48.1 wherein, X', Y, R1, R2, R3, m and n are as indicated in claim 1. 8. ' A urea as claimed in claim 1 having the formula: EMI48.2 wherein X, X', Y, R1, R2, R3, m and n are as indicated in claim 1. 9. A urea as claimed in any one of the preceding claims wherein Y is oxygen, X is hydrogen or halogen, X' is halogen, R1 is chlorine or methyl, R2 is halogen or C1-C4 alkyl, R3 is C1-C4 alkyl, m is 3 and n is 1 10. 1-[4-(2,4-dimethylphenoxy)-3,6-dimethyl-5chlorophenyl]-3-(2-chlorobenzoyl) urea. 11. 1-[4(2,4-dimethylphenoxy)-3,6-dimethyl-5chlorophenyl-3-(2,6-difluorobenzoyl)urea. 12. 1-[4-(3,5-dimethylphenoxy)-3,6-dimethyl-5chlorophenyl]-(2,6-diflorobenzoyl)urea. 13. 1-[4-(2-methyl-4-bromophenoxy)-3,6-dimethyl-5chlorophenyl]-3-(2-chlorobenzoyl)urea. 14. 1-[4-(2-methyl-4-bromophenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2,6-difluorobenzoyl)urea. 15. 1-[4-(2-methyl-4-chlorophenoxy)-3,6-dimethyl-5 chlorophenyl] -3- (2- chlorobenzoyl) urea. 16. 1-14- {2-methyl 4-chlorophenoxy) -3, 6-dimethyl-5- chlorophenyl]-3-(2,6-difluorobenzoyl)urea. 7. 1-[4-(2-methyl-4-tertiary-butylphenoxy)-3,6 dimethyl-5-chlorophenyl]-3-(2,6- difluorobenzoyl) urea. 18. 1- t4- (2,3,5-trimethylphenoxy) -3,6-dimethyl-5- chlorophenyl]-3-(2,6-diflorobenzoyl)urea. 19. 1- X4- (3, 5-dimethyl-4-chlorophenoxy) -3, 6-dimethyl-5- chlorophenylj -3- (2, 6-difluorobenzoyl) urea. 20. 1-14-(2,3-dimethyl-4-bromophenoxy)-3,6-dimethyl-5- chlorophenyl]-3-(2-chlorobenzoyl)urea. 21. 1-[4-(2,5-dimethyl-4-chlorophenoxy)-3,6-dimethyl-5 chlorophenyl]-3-(2,6-difluorobenzoyl)urea. 22. 1-[4-(2,5-dimethylphenoxy)-3,6-dimethyl-5-chloro phenyl]-3-(2,6-difluorobenzoyl)urea. 23. 1-[4-(2,5-dimethylphenoxy)-3,6-dimethyl-5-chloro phenyl]-3-(2-chlorobenzoyl)urea. 24. 1-[4-(2,4,5-trimethylphenoxy)-3,6-dimethyl-5-chloro phenyl]-3-(2,6-difluorobenzoyl)urea. 25. 1-[4-(2,4,5-trimethylphenoxy)-3,6-dimethyl-5-chloro phenyl]-3-(2-chlorobenzoyl)urea. 26. 1- t4- (2,5-dimethyl-4-bromophenoxy) -3 ,6-dimethyl-5- chlorophenyl]-3-(2,6-difluorobenzoyl)urea. 27. 1- t4- (2, 5-dimethyl-4-cyarlophenoxy) -3, 6-dimethyl-5- chlorophenyl]-3-(2,6-difluorobenzoyl)urea. 28. 1-[4-(2,5-dimethyl-4-trifluoromethylphenoxy)-3,6 dimethyl-5-cfilorophenyl]-3- (2,6-difluorobenzoyl) urea. 29. A pesticide composition comprising an acceptable carrier and a pesticidally effective amount of a urea as claimed in any one of the preceding claims. 30. A method of controlling pests which comprises subjecting said pests to a pesticidally effective amount of a urea or of a composition as claimed in any of the preceding claims. 31. A method of preparing a l-(alkyl phenoxyaryl) -3-benzoyl urea of the general formula: EMI52.1 wherein X. X' are independently hydrogen. halogen. C1-C4 alkyl. haloalkyl. polyhaloalkyl. alkoxy. polyhaloalkoxy Y represents oxygen or sulfur: in. n are independently 0-4 ; R1 represents hydrogen. halogen. C1-C4 alkyl haloalkyl. polyhaloalkyl, or alkoxy, R2 represents hydrogen. halogen. C1-C4 alkyl, polyhaloalkyl. polyhaloalkoxy. Cl-C8 alkylsulfonyl. C1-C8 alkoxy, - C1-C8 alkylthio. C1-C8 dialkylamino, CN, NO2. CO2R4, or CONHR4 wherein R4 -represents C1-C8 alkyl; and R3 represents C1-C12 alkyl, with' the proviso that m may not be O or 1 when n is less than 2, which method comprises reacting a benzoyl isocyanate pr a benzoyl isothiocyanate of the formula: EMI52.2 with an alkylphenoxyaniline of the formula: EMI53.1 wherein X, X', Y, R1, R2, R2, m and n have the meanings set forth above, and thereafter recovering the urea. 32. A method of preparing a l-(alkyl phenoxyaryl)-3-benzoyl urea of the general formula: EMI53.2 wherein X. X' are independently hydrogen. halogen; C -C alkyl, 14 haloalkyl. polyhaloalkyl. alkoxy. polyhaloalkoxy Y represents oxygen or sulfur: m, n are independently 0-4 R1 represents hydrogen, halogen, C1-C4 alkyl, haloalkyl, polyhaloalkyl, or alkoxy, R2 represents hydrogen. halogen, C1-C4 alkyl, polyhaloalkyl, polyhaloalkoxy. Cl-Cs alkylsulfonyl, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 dialkylamino, CN, NO2, CO2R4, or CONHR4 wherein R4 represents C1-C8 alkyl; and R3 represents C1-C12 alkyl, with the proviso that m may not be O or 1 when n is less than 2, which method comprises reacting an alkylphenoxyphenyl isocyanate or alkylphenoxyphenyl isothiocyanate of the formula: EMI54.1 with a benzamide of the formula: EMI54.2 wherein X, X', Y, R11 R2, , R3, mand n have the meaningS set forth above, and thereafter recovering the urea. 33. A method as claimed in claim 31 or 32 wherein the urea is 1-[4-(2,4-dimethylphenoxy)-3,6- dimethyl-5-chlorophenyl]-3-(2-chlorobenzoyl)urea. 34. A method as claimed in claim 31 or 32 wherein the urea is l-C4-(2,4-dimethylphenoxy)-3,6- dimethyl-5-chlorophenyl]-3-(2,6-difluorobenzoyl)urea.

Inventors: CAIN, PAUL ALFRED, CHOU, DAVID TEH-WEI
Applicants: UNION CARBIDE CORPORATION
Application year: 1983
Main classification: C07C127
IPC codes: C07C275, C07C205, A01N47, C07C335