PESTICIDAL BENZOYLUREA COMPOUNDS

Abstract: A benzoylurea compound of formula:- in which each of P and Q independently represents a halogen atom or an alkyl group; m represents 0, 1 or 2; R represents an optionally-substituted alkyl, alkenyl, alkynyl, cycloalkyl or phenyl group, a hydrogen atom, one equivalent of an alkali metal or alkaline earth metal, or an ammonium or substi­ tuted ammonium group; each X independently represents a halogen atom, a cyano, nitro or carboxy group, or an optionally-substituted alkyl, alkoxy, alkylthio, cycloalkyl, cyc­ loalkyloxy, cycloalkylthio, alkenyl, alkentylthio, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, alkynyl, phenyl, phenoxy, phenylthio or amino group; q = 0,1,2,3 or 4; T represents a halogen atom, an alkyl, haloalkyl, alkoxy, haloalkoxy, alkenyloxy or haloalkenyloxy group, or a phenoxy or pyridy­ loxy group optionally substituted by one or more substi­ tuents selected from halogen atoms and nitro, alkyl, haloal­ kyl and cyano groups; each Y independently represents a halogen atom or a nitro, cyano, alkyl or haloalkyl group; and p = 0, 1, 2, 3 or 4. The compounds have pesticidal activity, and may be prepared from novel sulphenamide starting materials.

Description: PESTICIDAL BENZOYLUREA COMPOUNDS The present invention relates to benzoylurea compounds and their preparation, to compositions containing such compounds, and to their use as pesticides. GB 1,460,410 and GB 1,501,607 disclose that certain disttstituted ureas have pesticidal activity. The Applicants have now discovered that a further class of novel urea derivatives have pesticidal activity. These ureas are trisubstituted, and contain a specifically-substituted phenylthio group. Accordingly, the present invention provides a benzoylurea compound of formula : EMI1.1 in which each of P and Q independently represents a halogen atan or an alkyl group; m represents 0, 1 or 2; R represents an optionally-substituted alkyl, alkyl, alkyl, cycloalkyl or phenyl group, a hydrogen atom, one equivalent of an alkali metal or alkaline earth metal, or an ammonium or substituted ammonium group; each X independently represents a halogen atom, a cyano, nitro or carboxy group, or an optionally-substituted alkyl, alkoxy, alkylthio, cyclcalkyl, cycloalkyloxy, cycloalkylthio, alkenyl, alkenylthio, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, alkynyl, phenyl, phenoxy, phenylthio or amino group; q = 0, 1, 2, 3 or 4; T represents a halogen aran, an alkyl, haloalkyl, alkoxy, halcalkoxy, alkenyloxy or haloalkenyloxy group, or a phenoxy or pyridyloxy group optionally substituted by one or more substituents selected fran halogen atoms and notro, alkyl, haloalkyl and cyano groupes ; each Y independently represents a halogen atan or a nitro, cyano, alkyl or halcalkyl group; and p = 0, 1, 2, 3 or 4. Except where otherwise stated, throughout this Specification and claims, alkyl, alkenyl and alkynyl moieties preferably have up to 6, especially up to 4, carbon atans, and cycloalkyl groups preferably have 3 to 7 ring carbon atans. Halogen atoms may be iodine, bromibe, chlorine or fluorine atans, with fluorine and chlorine atans being preferred. A heterocyclyl group preferably contains one oxygen, sulphur or nitrogen atan, rray be saturated or unsaturated, and preferably has 5 or 6 atoms in the ring. Optional substituents which may be present in an optionally substituted alkyl, alkenyl or alkynyl moiety include halogen atoms, alkoxy, haloalkoxy, hydroxy, carboxy, alkoxycarbonyl, cycloalkyl and heterocyclyl groups, groups of formula -O-(CH2CH2O)nalkyl where n is 1 to 4, and optionally substituted phenyl groups. These substituents may also be present in optionally substituted cycloalkyl groups, along with alkyl and haloalkyl groups. Optional substituents which may be present in optionally substituted phenyl, phenoxy and pyridyloxy groups include halogen atans and alkyl, haloalkyl, alkoxy, haloalkoxy, alkenyl, haloalkenyl, nitro and cyano groups. Preferably each of P and Q indepandently represents a C(1-4) alkyl, especially methyl, group, or a fluorine, chlorine or bromine atom, and m is 0 or 1. If m is 1, Q is preferably in the 6 position of the phenyl ring. Preferably T represents a bromine or, especially, fluorine or chlorine atom; a C(1-4) alkyl, haloalkyl or haloalkoxy group, especially a methyl, trifluoromethyl or trifluoromethoxy group ; an optionally substituted phenoxy group in which the optional substituents are selected fran C(1-4) alkyl and haloalkyl, especially methyl and trifluoromethyl, groups, fluorine and chlorine atans, and nitro and cyano groups; or an optionally substituted pyridyloxy group in which the optional substituents are selected fran trifluoranetbyl groups and fluorine and chlorine atans. When T contains a pyridyl group; the pyridyl moiety is preferably a 2-pyridyl moiety; if this 2-pyridyl piety is substituted, it preferably bears halogen or haloalkyl, especially trifluoromethyl, substituents, preferably in the 3-, 5- or 3,5- positions. When T is a trifluoromethylphenoxy group this is preferably a 4-trifluoromethylphenoxy group and, when the phenoxy moiety thereof is further substituted, this substitution is preferably in the 2-position. Thus 2-chloro-4-trifluoromethylphenoxy, 2-fluoro-4-trifluoromethylphenxoy and 2-cyano-4-trifluoromethylphenoxy are preferred examples of the group T. Preferably p = 1 when T is a 4-substituted phenoxy group, or p = 0 when T is a 4-substituted-phenoxy group bearing a second substituent. Preferably Y represents a fluorine, chlorine or bromine atom, a C(1-4) alkyl or haloalkyl group, or a nitro ar cyano group. Preferably p is 0, 1 or 2. Preferably X represents a bromine or, especially, chlorine or fluorine atom, or a C(1-4) alkyl group. Preferably q is 0 or 1, especially 0. Preferably R represents an optionally substituted alkyl group containing 1 to 20, especially 1 to 15, carbon atoms, a C(3-6) cycloalkyl group, or an optionally substituted phenyl group. Preferred substiteents in an optionally substituted phenyl group R are selected fran C(1-4) alkyl and haloalkyl groups, such as methyl and trifluoromethyl groups, nitro and cyano groups, and halogen atans, especially fluorine and chlorine atans. Preferred subtiteents in an optionally substituted alkyl group R are halogen atans, especially chlorine and fluorine atans; C(1-4) alkoxy groups, especially methoxy and ethoxy groups; cartay groups; alkoxycarbonyl groups containing 2 to 5 carbon atoms, for example ethoxycarbonyl and methoxycarbonyl groups; groups of formula -O-(CH2CH2O)nalkyl where n is 1 to 4, especially 1, and the alkyl moiety has 1 to 4, especially 1 or 2, carbon atans; optionally substituted phenyl groups in which the preferred optional substituents are as given above for an optionally substituted phenyl group R; and heterocyclic groups, especially tetrahydrofuryl groups. In one preferred embodiment of the invention, R represents an unsubstituted alkyl group having i to 20 caooon atans, especially 1 to 10 carbon atans, most preferably 1 to 5 carbon atans. In a further preferred embodiment of the invention, R represents a group of general formula -(CH2CH2O)nRÚ (II) in which R1 represents an optionally-substituted alkyl, alkyl, alkynyl, cycloalkyl or phenyl group, and n represents 1, 2, 3, 4 or 5. Preferably R represents an alkyl or haloalkyl group containing 1 to 10 carbon atans, the halogen being chlorine or fluorine. Most preferably, R1 represents an alkyl group having 1 to 4 carbon atans, for example mehtyl, ethyl, isopropyl or tertiary butyl. Preferably n is 1 or 2. Preferably the group -COO(CH2Ch2O)RÚ is located on the 2-position of the phenyl ring of the phenylthio group. Thus typical benzoylureas according to the invention have the general formula I in which each of P and Q independently represents a fluorine, chlorine or bromine atam or an alkyl group containing 1 to 4 carbon atans and m represents 0 or 1; R represents an alkyl, haloalkyl or alkoxyalkyl group containing 1 to 15, especially 1 to 10, carbon atans and in which the halogen substituent is chlorine or fluorine and the alkoxy substituent contains 1 to 4 carbon atoms; one equivalent of an alkali metal or alkaline earth metal; or an ammonium or a C (1-6) alkyl-substituted-amnnium group; each X represents a fluorine, chlorine or bromine atom, or an alkyl group of 1 to 4 carbon atans and q = 0, 1, 2, 3 or 4; T represents a fluorine, chlorine or branine atom, a halcalkyl or haloalkoxy group of 1 to 4 carbon atans in which the halogen substituent is fluorine, chlorine and/or bromine, or a trihalomethyl-, nitro, or cyano-phenoxy group in which the phenoxy moiety can also bear one or itore fluorine, chlorine or bromine, C(1-4)alkyl, nitro or cyano substituents; each Y independently represents a fluorine, chlorine, or bromine atom, a nitro or cyano group, or a C(1-4)alky1 or haloalkyl group in which the halogen substituent is fluorine, chlorine or bromine; and p = 0, 1, 2, 3 or 4. More preferred benzoylureas according to the invention have the general formula I in which each of P and Q independently represents a fluorine, chlorine or branine atom ; m represents 0 or 1; R represents a C(1-10) alkyl or haloalkyl group in which the halogen substituent is fluorine or chlorine; q = 0; T represents a chlorine atom, a fluoroalkyl or fluoroalkoxy group of 1 to 4 carbon atoms and 1 to 5 fluorine atans, or a trifluoromethylphenoxy group in which the phenoxy moiety can also bear one or itore fluorine, chlorine or branine atans; each Y independently represents a fluorine or chlorine atom; and p = 0, 1, 2, 3 or 4. The -COOR substituent in the phenylthio group of the benzoylureas of formula I may be located in any one of the available positions on the phenyl ring but it is preferably located in the 2-position. The invention also provides a process for preparing the novel benzoylurea compounds, which comprises reacting a benzoyl isocanate of formula: EMI6.1 with a sulphenamide of formula : EMI6.2 in which P, Q, m, R, X, q, T, Y and p have the meanings specified above. Tie reaction is suitably carried out in the presence of a solvent. Suitable solvents are aromatic solvents such as benzene, toluene, xylene, or chlorobenzene, hydrocarbons such as petroleum fractions, chlorinated hydrocarbons such as chloroform, methylene chloride or dichloroethane, and ethers such as diethylether, dibutylether, or dioxan. Mixtures of solvents are also suitable. Preferably the reaction is carried cut at a tneerature from 0 C to 100 C, suitably ambient temperature. Preferably the molar ratio of benzoyl-isocyanate to sulphenamide is fran 1:1 to 2:1. Preferably the reaction is carried cut under anhydrous conditions. The sulphenamide intermediates IV are themselves novel and constitute a further aspect of the invention; they may be prepared by reacting a suiphenyl halide of formula: EMI7.1 wherein X, q and R have the meanings specified above in relation to formula I and Hal represents a halogen atom, preferably a chlorine or branine atan, with an aniline of formula: EMI7.2 wherein T, Y and p have the meanings specified above in relation to formula I in the presence of a dehydrohalogenating agent, such as an organic or inorganic base. Suitable bases include alkali tretal hydroxides, amides or alkoxides, for example, sodium ethoxide; alkali metal or alkaline earth metal hydroxides, for example, potassium hydroxide ; and primary, secondary or tertiary mines, for example, triethylamine or piperidine. The reaction is conveniently carried out in the presence of an aprotic solvent; suitable solvents include aromatic solvents such as benzene, toluene, xylene or chlorobenzene, hydrocarbons such as petroleum, chlorinated hydrocarbons, such as methylene chloride, and ethers such as diethyletber and dibutylether. The e reaction is suitably carried out at a temperature in the range of -10 to 50 C, preferably -5 to 200C. The sulphenyl halide of formula V may be prepared from the corresponding thiol or disulphide, e.g. according to the method of L. Katz, L.S. Karger, W. Schroeder and M.S. Cohen, J. Org. Chem., 1953, 18, 1380. In the preparation of the intermediates IV the sulphenyl halide V starting material may be prepared in situ. The disulphide starting material for the sulphenyl halide of fomrula V may be prepared by the esterification of the corresponding dicarboxylic acid according to the method of J.C. Grivas, J. Org. Chem. 1975, 40, 2029. The compounds of the present invention have been found to have high insecticidal and acaricidal activity. Accordingly the present invention also provides pesticidal compositions comprising a compound of for I as defined above together with a carrier. Such a composition may contain a single compound or a mixture of several compounds of the invention. be invention further provides a method of combating pests at a locus, which ccoprises applying an insecticidally effective amount of a benzoylurea compound or composition according to the present invention to the locus. Unlike the compounds of the prior art, which are virtually insoluble in organic solvents and therefore extremely difficult to formulate without great expense, the compounds of the general formula I are in general readily soluble in organic solvents making formulation relatively simple, and the resulting compositions easy to handle and economically attractive. The compounds of the general formula I also appear to possess a faster mode of action than the compounds of the prior art. A carrier in a ccmpositian according to the invention is any material with which the active ingredient is formulated to facilitate application to the locus to be treated, which may for example be a plant, seed or soil, or to facilitate storage, transport or handling. A carrier may be a solid or a liquid, including a material which is normally gaseous but which has been compressed to form a liquid, and any of the carriers normally used in formulating pesticidal compositions may be used. Preferably compositions according to the invention contain 0.5 to 95% by weight of active ingredient. Suitable solid carriers include natural and synthetic clays and silicates, for example natural silicas such as diatomaceous ears; magnesium silicates, for example talcs; magnesium aluminium silicates, for example attapulgites and vermiculites ; aluminium silicates, for example kaolinites, rrontatorillonites and micas; calcium carbonate; calcium sulphate; synthetic hydrated silicon oxides and synthetic calcium or aluminium silicates; elements, for example carbon and sulphur; natural and synthetic resins, for example coumarons resins, polyvinyl chloride, and styrene polymers and copolymers; solid polychIorophenols; bitumen ; waxes, for example beeswax, paraffin wax, and chlorinated mineral waxes; and solid fertilisers, for example superphosphates. Suitable liquid carriers include water; alcohols, for example isopropanol and glycols; ketones, for example acetone, methyl ethyl ketone, methyl iscbutyl ketone and cyclohexanone ; ethers; aromatic or araliphatic hydrocarbons, for example benzene, toluene and xylene; petroleum fractions, for example kerosine and light mineral oils; chlorinated hydrocarbons, for example cabin tetrachloride, perchloroethylene and trichloroethane. Mixtures of different liquids are often suitable. Agricultural compositions are often formulated and transported in a concentrated fran which is subsequently diluted by the user before application. The presence of small amounts of a carrier which is a surface-active agent facilitates this process of dilution. Thus preferably at least one carrier in a compo- sition according to the invention is a surface-active agent. For example the composition may contain at least two carriers, at least one of which is a surface-active agent. A surf aos-active agent may be an emulsifying agent, a dispersing agent or a wetting agent; it may be nonionic or ionic. Examples of suitable surface-active agents include the sodium or calcium salts of polyacrylic acids and lignin sulphonic acids; the condensation of fatty acids or aliphatic amazes or amides containing at least 12 carbon atans in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitan, sucrose or pentaerythritol ; condensates of these with ethylene oxide and/or propylene oxide; condensation products of fatty alcohol or alkyl phenols, for example p-octylphenol or or p- octylcresol, with ethylene oxide and/or propylene oxide; sulphates or sulpbonates of these condensation products; alkali or alkaline earth metal salts, preferably sodium salts, of sulphuric or sulphonic acid esters containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulfate, sodium secondary alkyl sulphates, sodium salts of sulphonated castor oil, and sodium alkylaryl sulphonates such as sodium dodecylbenzene sulphonate ; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide. She compositions of the invention may for exairple be formu- lated as wettable powders, dusts, grannies, solutions, eitulsifi- able concentrates, emulsions, suspension concentrates and aerosols. Wettable powders usually contain 25, 50 or 75% w of active ingredient and usually contain in addition to solid inert carrier, 3-10% w of a dispersing agent and, where necessary, 0-10% w of stabilispr(s) and/or other additives such as penetrants or stickers. Dusts are usually formulated as a dust concentrate having a similar composition to that of a wettable powder but without a dispersant, and are diluted in the field with further solid carrier to give a compositicn usually containing h-10% w of active ingredient. Granules are usually prepared to have a size between 10 and 100 BS mesh (1.676 - 0.152 mm), and may be manufactured by agglomeration or impregnation techniques. Generally, granules will contain h-75% w active ingredient and 0-10% w of additives such as stabilisers, surfactants, slow release modifiers and binding agents. The so-called "dry flowable powders" consist of relatively small granules having a relatively high concentration of active ingredient. Emulsifiable concentrates usually contain, in addition to a solvent and, wben necessary, co-solvent, 10-50% w/v active ingrdient, 2-20% w/v emulsifiers and 0-208 w/v of other additives such as stabilisers, penetrants and corrosion inhibitors. Suspension concentrates are usually compounded so as to obtain a stable, non-seinnenting flowable product and usually contain 10-75% w active ingredient, 0.5-15% w of dispersing agents, 0.1-10% w of suspending agents such as protective colloids and thixotropic agents, 0-10% w of other additives such as defoamers, corrosion inhibitors, stabilisers, penetrants and stickers, and water or an organic liquid in which the active ingredient is substantially insoluble; certain organic solids or inorganic salts may be present dissolved in the formulation to assist in preventing sedimentation or as anti-freeze agents for water. Aqueous dispersions and emulsions, for example compositions obtained by diluting a wettable powder or a concentrate according to the invention with water, also lie within the scope of the present invention. The said emulsions may be of the water-in-oil or of the oil-in-water type, and may have a thick 'mayonnoise'- like consistency. The composition of the invention may also contain other ingredients, for example, other compounds possessing pesticidal properties. Further insecticidal compounds may be included, particularly such compounds having a different node of activity. The following Examples illustrate the invention. Example A is concereed with the synthesis of a novel srllphenamide starting material, Examples 1-63 are concerned with the synthesis of the novel benzoylureas, and Example 64 with the biological activity of the novel benzoylureas. Example 65 to 114 give details of novel intermediates of the general formula IV. Example A Preparation of isopropyl 2-[[[4-(trifluoromethoxy)phenyl] anino] thio]benzoate A solution of branine (0.65ml) in dry methylene chloride (10ml) was added over thirty minutes to a stirred solution of diisopropyl 2,2'-dithiobisbenzoate (4.9g) in the sane solvent (40ml) at ambient temperature. The resulting dark red solution was stirred at this ternerature for 1.25 hours and was then added over thirty minutes to a stirred solution of 4 (trifluoromethoxy)aniline (4. 45g) in dry methylene chloride (lOOml) containing triethylamine (5.0ml). The temperature of the reaction mixture was kept at 5-100C throughout the addition by means of an ice bath and when the addition had been completed, the reaction was allowed to warm m to ambient temperature over 4.0 hours. The solvent was removed under reduced pressure and the residue was suspended in diethyl ether (250ml) and washed with water to remove triethylamine hydrobromide. The resulting diethyl ether solution was dried using magnesium sulphate and evaporated to yield the crude product which was prrified by crystallisation fran dimethyl ether/light petroleum The crystallisation yielded 7.4g of the desired product as colourless plates, melting point 120-121 C. The following analytical results were obtained : - Calculated: C: 55.0% H: 4.3% N: 3.8% Found: C: 55.0% H: 4.5% N: 3.8% Example 1 Preparation of isopropyl 2-[[[[(2-chlorobenzoyl)amino]carbonyl][3-(trifluoromethoxy)phenyl]amino]thio]benzoate A solution of 2-chlorienzoyl isocyanate (2.7g) in dry toluene (5.0ml) was added to a stirred suspension of isopropyl 2-[[[4-(trifluoromethoxy)phenyl]amino]thio]benzoate (3.7g) in the same solvent (20.0ml) at roan temperature. After 18 hours, a cake of crystals had formed. The reaction mixture was ccoled to -50C and filtered, washing the crystals with cold toluene followed by light petroleum. After drying at 40 C under vacuum, the pure product was obtained as colourless crystals (4.8g). Malting point 143-1440C. The following analytical results were cbtained:- Calculated: C: 54.3% H: 3.78 N: 5.18 Found: C: 54.5% H: 3.58 N: 5.2% Example 2 Preparation of butyl 2-[[[[(2,6-difluorobenzoyl)amino]carbonyl]- [4-(trifluoromethyl)phenyl]amino]thio]benzoate A solution of 2,6-difluorobenzoyl isocyanate (1.1g) in dry toluene (5.0ml) was added to a stirred solution of butyl 2-[[[4- (trifluoromethyl)phenyl]amino]thio]benzoate (1.9g) in the sane solvent (7.0ml) at room temperature. After 18 hours, the reaction mixture was cooled to -5 , and the crystalline precipitate was separated, washing with cold toluene followed by light petroleum. The pure product was cotained as colourless crystals (2.5 g, melting point 79-81 ) after recrystallisation from diethyl ether/ light petroleum. The following analytical results were obtained:- Calculated: C: 56.58 H: 3.8% N: 5.1% Found: C: 56.3% H: 4.0% N: 5.1% Example 3 Preparation of propyl 2-[[[4-[2-chloro-4-(trifluoromethyl)- phenoxyphenyl] [[(2,6-difluorobenzoyl)amino]carbonyl]aminothio]benzoate A solution of 2,6-difluorobenzoyl isocyanate (l.8g) in dry toluene (5.0ml) was added to a stirred solution of propyl 2 [[[[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]amino]thio]benzoate (3.6g) in the sane solvent (7.0ml) at roan temperature. After 4.0 hours, the reaction mixture was evaporated under reduced pressure and the product was isolated fran the residue by rapid chromatography on silica gel using methylene chloride as eluent. Crystallisation from diethyl ether/ light petroleum afforded the pure product as colourless crystals (4.2g) melting point 148-150 . The following analytical results were obtained : - Calculated: C: 56.0% H: 3.3% N: 4.2% Found: C: 56.3% H: 3.3% N: 4.3% Example 4 Preparation of ethyl 2-[[[[(2-chlorobenzoyl)amino]carbonyl] [4-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]amino]thio]benzoate A solution of 2-chlorobenzoyl isocyanate (1.8g) in dry toluene (5.0ml) was added to a stirred solution of ethyl 2-[[[[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]amino]thio]benzoate (3.5g) in the same solvent (7.0 ml) at roan temperature. After 18.0 hours, the reaction mixture was diluted with dry light petroleum (30ml) and the resulting precipitate of crude product was separated, washing with light petroleum. This material was purified by rapid chromatography on silica gel followed by crystallisation from diethyl ether/light petroleum. The crystallisation yielded 3.lg of the desired product as colourless crystals, melting point 98-100 C. The following analytical results were cbtained:- Calculated : C: 55.5% H: 3.2% N: 4.3% Found: C: 55.6% H: 3.2% N: 4.3% Examples 5 to 63 In Examples S to 63 compounds were prepared by one of the methods described in Examples 1 to 4. The carpounds, their melting points and chetnical analyses are shown in Table 1 below. TABLE 1 EMI15.1 Example Analysis % NO. T R P Q U V m.p. ( C) C H N 5 2-Cl-4-CF3-C6H3-O- Sec-C4H9- F F H H 77-79 Calc. 56.6 3.5 4.1 Found. 56.8 3.9 4.0 6 -OCF3 CH3 Cl H H H 144-145 Calc. 52.6 3.1 5.3 Found. 52.7 2.9 4.8 7 -OCF3 C2H5 Cl H H H 150-152 Calc. 53.5 3.4 5.2 Found. 53.6 3.2 5.3 8 -OCF3 n-C3H7 Cl H H H 122-123 Calc. 54.3 3.7 5.1 Found. 54.5 3.6 5.2 9 -OCF3 n-C4H9 Cl H H H 111-113 Calc. 55.1 3.9 4.9 Found. 55.1 3.7 5.0 Table 1 (continued Example Analysis % NO. T R P Q U V m.p. ( C) C H N 10 -OCF3 -CH(CH3)CH2CH3 Cl H H H 118-119 Calc. 55.1 3.9 4.9 Found. 54.8 3.7 5.0 11 -OCF3 n-C5H11 Cl H H H 88-89 Calc. 55.8 4.2 4.8 Found. 55.9 3.7 5.2 12 -OCF3 -CH(CH3)CH2CH2CH3 Cl H H H 119-120 Calc. 55.8 4.2 4.8 Found. 55.8 3.8 5.0 13 -CF3 CH3 F F H H 161-163 Calc. 54.1 2.9 5.5 Found. 54.8 3.5 5.4 14 -CF3 C2H5 F F H H 137-140 Calc. 55.0 3.2 5.3 Found. 55.4 3.1 5.5 15 -CF3 n-C3H7 F F H H 140-143 Calc. 55.8 3.5 5.2 Found. 55.5 3.4 5.3 16 -CF3 i-C3H7 F F H H 155-157 Calc. 55.8 3.5 5.2 Found. 55.7 3.4 5.4 17 -CF3 (CH2)2CH(CH3)2 F F H H 139-141 Calc. 57.2 4.1 5.0 Found. 58.1 4.0 4.9 Table 1 (continued Example Analysis % NO. T R P Q U V m.p. ( C) C H N 18 -CF3 CH2CF3 F F H H 80-82 Calc. 49.8 2.4 4.8 Found. 50.4 2.4 4.8 19 2-Cl-4-CF3-C6H3-O- CH3 F F H H 135-137 Calc. 54.7 2.8 4.4 Found. 54.9 2.8 4.5 20 2-Cl-4-CF3-C6H3-O- C2H5 F F H H 126-128 Calc. 55.3 3.1 4.3 Found. 55.5 3.0 4.3 21 2-Cl-4-CF3-C6H3-O- n-C4H9 F F H H 124-126 Calc. 56.6 3.5 4.1 Found. 56.7 3.4 4.2 22 2-Cl-4-CF3-C6H3-O- -CH(CH3)CH2CH3 F F H H 77-79 Calc. 56.6 3.5 4.1 Found. 56.8 3.9 4.0 23 2-Cl-4-CF3-C6H3-O- n-C5H11 F F H H 63-65 Calc. 57.2 3.8 4.0 Found. 56.7 3.5 4.1 24 2-Cl-4-CF3-C6H3-O- -CH(CH3)CH2CH2CH3 F F H H 70-72 Calc. 57.2 3.8 4.0 Found. 57.2 3.9 4.3 25 2-Cl-4-CF3-C6H3-O- CH3 Cl H H H 139-141 Calc. 54.8 3.0 4.4 Found. 54.3 3.1 4.6 Table 1 (continued Example Analysis % NO. T R P Q U V m.p. ( C) C H N 26 2-Cl-4-CF3-C6H3-O- n-C3H7 Cl H H H 135-379 Calc. 56.1 3.5 4.2 Found. 56.1 3.6 4.2 27 2-Cl-4-CF3-C6H3-O- n-C4H9 Cl H H H 119-121 Calc. 56.7 3.7 4.1 Found. 56.7 3.4 4.1 28 2-Cl-4-CF3-C6H3-O- -(CH2)2CH(CH3)2 F F H H Gum Calc. 57.2 3.8 4.0 Found. 56.7 4.1 3.8 29 2-Cl-4-CF3-C6H3-O- -(CH2)9CH3 F F H H 48-52 Calc. 59.8 4.7 3.7 Found. 59.5 5.0 3.6 30 2-Cl-4-CF3-C6H3-O- -(CH2)13CH3 F F H H Gum Calc. 61.6 5.4 3.4 Found. 61.6 5.7 3.4 31 2-Cl-4-CF3-C6H3-O- -(CH2)15CH3 F F H H Gum Calc. 62.4 5.7 3.3 Found. 62.0 5.8 3.4 32 2-Cl-4-CF3-C6H3-O- cyclohexyl F F H H 98-100 Calc. 57.4 3.7 4.0 Found. 58.3 4.1 3.9 33 2-Cl-4-CF3-C6H3-O- benzyl F F H H 88-91 Calc. 59.0 3.1 3.9 Found. 58.8 3.0 3.8 Table 1 (continued Example Analysis % NO. T R P Q U V m.p. ( C) C H N 34 2-Cl-4-CF2-C6H3-O- phenyl F F H H 96-99 Calc. 58.4 2.9 4.0 Found. 58.6 3.0 4.0 35 2-Cl-4-CF2-C6H3-O- -CH(CH3)CO2C2H5 F F H H 81-84 Calc. 54.8 3.3 3.9 Found. 55.0 3.3 3.8 36 2-Cl-4-CF3-C6H3-O- -CH2CO2C2H5 F F H H 78-80 Calc. 54.2 3.1 4.0 Found. 54.4 3.0 3.9 37 2-Cl-4-CF3-C6H3-O- 2-tetrahydrofuryl- F F H H 83-86 Calc. 56.1 3.4 4.0 methyl Found. 55.8 3.4 4.2 38 Cl n-C3H7 F F H H 105-108 Calc. 57.1 3.8 5.6 Found. 56.6 3.6 5.6 39 Cl Sec-C4H9 F F H H 75-783 Calc. 57.9 4.1 5.4 Found. 57.7 4.1 5.4 40 OCF3 n-C3H7 F Cl H H 124-125 Calc. 52.6 3.3 4.9 Found. 52.7 3.2 4.0 41 OCF3 Sec-C4H9 F Cl H H 99-100 Calc. 53.4 3.6 4.8 Found. 53.7 3.9 4.7 Table 1 (continued Example Analysis % NO. T R P Q U V m.p. ( C) C H N 42 OCF3 n-C3H7 F F H H 98-100 Calc. 54.1 3.4 5.0 Found. 53.7 3.5 5.3 43 OCF3 Sec-C4H9 F F H H 109-110 Calc. 54.9 3.7 4.9 Found. 55.1 4.0 4.9 44 CF3 C2H5 F Cl H H 145-147 Calc. 53.3 3.2 5.2 Found. 53.4 3.3 5.2 45 2-Cl-4-CF3-C6H3-O- -CH2CH2OCH3 F F H H 85-86 Calc. 54.7 3.2 4.1 Found. 54.9 3.1 4.2 46 2-Cl-4-CF3-C6H3-O- -CH2CH2OC2H5 F F H H 64-66 Calc. 55.3 3.5 4.0 Found. 55.2 3.2 4.3 47 2-Cl-4-CF3-C6H3-O- -(CH2CH2O)2CH3 F F H H 86-87 Calc. 54.7 3.6 3.9 Found. 54.7 3.5 3.9 48 2-Cl-4-CF3-C6H3-O- -(CH2CH2O)2C2H5 F F H H 52-56 Calc. 55.2 3.8 3.8 Found. 54.9 3.9 3.9 49 3-Cl-4-CN-C6H3-O- n-C3H7 Cl H Cl Cl 111-114 Calc. 54.0 3.1 6.1 Found. 53.3 3.1 5.8 Table 1 (continued Example Analysis % NO. T R P Q U V m.p. ( C) C H N 50 3-Cl-4-CN-C6H3-O- Sec-C4H9 Cl H Cl Cl 99-101 Calc. 54.6 3.3 6.0 Found. 53.9 3.3 5.7 51 4-CN-C6H4-O- n-C3H7 Cl H Cl H 98-99 Calc. 60.0 3.7 6.8 Found. 59.6 3.6 6.6 52 4-CN-C6H4-O- Sec-C4H7 Cl H Cl H 114-116 Calc. 60.6 3.4 6.6 Found. 60.3 3.8 6.4 53 4-NO2-C6H4-O- n-C3H7 Cl H Cl Cl 122-124 Calc. 53.4 3.3 6.2 Found. 53.4 3.2 6.1 54 3,5-dichloro-2- Sec-C4H9 F F Cl H 112-115 Calc. 52.9 3.2 6.2 pyridyloxy Found. 52.8 3.3 5.9 55 3,5-dichloro-2- n-C3H7 F F Cl H 110-112 Calc. 52.2 3.0 6.3 pyridyloxy Found. 52.5 3.1 5.9 56 3,5-dichloro-2- Sec-C4H9 F F Cl Cl 140-142 Calc. 50.3 2.9 5.9 pyridyloxy Found. 49.9 3.0 6.0 57 3,5-dichloro-2- n-C3H7 F F Cl Cl 158-160 Calc. 49.6 2.7 6.0 pyridyoxy Found. 49.8 2.6 6.0 Table 1 (continued Example Analysis % NO. T R P Q U V m.p. ( C) C H N 58 4-NO2-C6H4-O- n-C3H7 F F Cl Cl 115-118 Calc. 53.3 3.1 6.2 Found. 52.8 2.9 6.2 59 4-NO2-C6H4-O- Sec-C4H9 F F Cl Cl 113-116 Calc. 53.9 3.3 6.1 Found. 53.8 3.3 5.9 60 4-NO2-C6H4-O- n-C5H11 F F Cl Cl 105-108 Calc. 54.5 3.6 6.0 Found. 54.5 3.6 5.9 61 4-NO2-C6H4-O- n-C4H9 F F Cl Cl 100-103 Calc. 53.9 3.3 6.1 Found. 54.2 3.4 5.9 62 4-NO2-C6H4-O- n-C4H9 F Cl Cl Cl 147-149 Calc. 52.7 3.3 5.9 Found. 52.5 2.9 5.9 63 4-NO2-C6H4-O- n-C5H11 F Cl Cl Cl 165 Calc. 53.3 3.5 5.8 Found. 53.6 3.4 5.8 Example 64 The insecticidal activity of the benzoylurea compounds of the invention was determined in the following tests. Test 1 The insecticidal and ovicidal activities of the compounds of the invention were assessed employing the pests Spodoptera littoralis (S.l.), Aedes zegypti (A.a) and eggs of littoralis (S.l.ov) The e test methods used for each species appear below. In each case the tests were conducted under normal conditions (23 C + 2 0C; fluctuating light and humidity). In each test an e0 for the compound was calculated fran the mortality figures and compared with the corresponding LC50 for ethyl parathion in the same tests. The results are expressed as toxicity indices thus: LC50(parathion) toxicity indices = x 100 (test and are set out in Table 2 below. (i) Spodoptera Littoralis Solutions or suspensions of the compound were made up over a range of concentrations in 108 acetone/water containing .025% Triton X100 ("Triton" is a registered trade mark). These solutions were sprayed using a logarithmic spraying machine onto petri dishes con taining a nutritious diet on which the Spodoptera littoralis larvae had been reared, When the spray deposit had dried each dish was infested with 10 2nd instar larvae. Mortality assessmants were made 7 days after spraying. (ii) Aedes Several solutions of the test compound of varying concentration were prepared in acetone. 100 microlitre quantities were added to 100ml of tap water, the acetone being allowed to evaporate off. 10 early 4th instar larvae were placed in the test solution; after 48 hours the (surviving) larvae were fed with animal feed pellets, and the final Fercentage mortality assessed when all the larvae had either pupated and emerged as adults or died. (iii) Spodoptera littoralis (ovicide) Solutions as described in (i) above were prepared. Eggs less than 24 hours old were cbtaied as follows. Adult Spodcg @a littoralis were held in large plastic cylinders. containing blotting paper on which the maths laid their batches of eggs. Egg batches containing approximately 60-70 eggs were cut frown the blotting paper with a lan surround. These were placed eggs uppermost on filter paper in the deeper half of 5cm disposable petri dishes and each batch of eggs was then sprayed with a different test solution or the control solution. The dishes were covered until the control eggs had hatched, approximately 5 days. The percentage ovicidal mortality was then.calculated. In Table 2, a dash sh indicates no results available, TABLE 2 Test Ccde Compound of Example S.l. A.a. S.l.ov 1 490 160 830 2 160 72 3,100 3 2,400 160 4 2,450 130 5 2,400 250 6 190 210 670 7 74 130 390 8 150 72 970 9 400 150 840 10 88 72 400 Test Code Carrpaund of Example S.1. A.a. S.l.ov 11 106 76 900 12 131 64 630 13 120 100 625 14 150 220 1,200 15 180 140 1,100 16 75 150 2,700 17 188 140 620 18 81 62 100 19 1,900 400 20 2,200 240 21 1,800 300 22 2,400 250 23 2,320 160 24 1,690 4 25 1,500 170 26 1,490 95 27 1,900 71 28 2,300 650 29 3,700 230 30 940 110 31 1,700 12 32 1,500 1,500 33 1,700 16 34 2,200 1,000 35 1,900 460 36 2,300 300 37 1,100 38 49 110 2,400 39 49 130 500 40 270 76 39 41 210 79 42 160 130 2,500 43 150 250 860 Test Code Compound of Example S.l. A.a. S.l.ov 44 94 82 45 2,500 780 46 1,450 850 47 1,860 860 48 1,180 670 49 430 110 50 120 110 51 170 85 52 75 88 53 1,200 150 54 960 1,500 55 1,000 240 56 2,100 1,400 57 1,100 350 58 2,000 580 59 - 1,200 530 - 60 1,800 - 500 61 2,100 210 62 63 Examples 65 to 114 Novel sulphenamide starting materials of the general formula IV were used in the synthesis of the compounds of Examples 1 to 63. Table 3 gives the physical data for each of these novel sulphenamides, which were prepared by the general 'tthed illustrated by Example A above. TABLE 3 EMI27.1 Example Analysis % NO. T R U V m.p. ( C) C H N 65 OCF3 i-C3H7 H H 120-121 Calc. 55.0 4.3 3.8 Found. 55.0 4.5 3.8 66 CF3 n-C4H9 H H 115-117 Calc. 58.5 4.9 3.8 Found. 58.4 4.9 3.8 67 2-Cl-4-CF3-phenoxy n-C3H7 H H 117-119 Calc. 57.3 4.0 2.9 Found. 57.4 3.9 2.9 68 2-Cl-4-CF3-phenoxy C2H5 H H 120-122 Calc. 56.5 3.6 3.0 Found. 56.3 3.7 3.0 69 2-Cl-4-CF3-phenoxy Sec-C4H9 H H 112-115 Calc. 58.1 4.2 2.8 Found. 58.0 4.3 2.8 70 OCF3 CH3 H H 100-101 Calc. 52.5 3.5 4.1 Found. 52.6 3.5 4.1 71 OCF3 C2H5 H H 123-125 Calc. 53.8 4.0 3.9 Found. 54.0 4.1 4.0 Table 3 (continued) Example Analysis % NO. T R U V m.p. ( C) C H N 72 OCF3 n-C3H7 H H 132-341 Calc. 55.0 4.3 3.8 Found. 55.2 4.3 3.9 73 OCF3 n-C4H7 H H 123-124 Calc. 56.1 4.7 3.6 Found. 56.0 4.9 3.7 74 OCF3 Sec-C4H9 H H 98-99 Calc. 56.1 4.7 3.6 Found. 56.3 4.6 3.9 75 OCF3 n-C5H11 H H 114-116 Calc. 57.1 5.1 3.5 Found. 57.1 4.7 3.7 76 OCF3 -CH(CH3)CH2CH2CH3 H H 85-86 Calc. 57.1 5.1 3.5 Found. 57.2 5.1 3.7 77 CF3 CH3 H H 164-166 Calc. 55.0 3.7 4.3 Found. 54.7 3.7 4.4 78 CF3 C2H5 H H 123-125 Calc. 56.3 4.1 4.1 Found. 56.2 4.1 4.2 79 CF3 n-C3H7 H H 129-132 Calc. 57.5 4.5 3.9 Found. 57.7 4.6 4.0 Table 3 (continued) Example Analysis % NO. T R U V m.p. ( C) C H N 80 CF3 i-C3H7 H H 133-135 Calc. 57.5 4.5 3.9 Found. 57.3 4.6 4.0 81 CF3 -(CH2)2CH(CH3)2 H H 142-144 Calc. 59.5 5.2 3.7 Found. 59.4 5.3 3.8 82 CF3 -CH2CF3 H H 104-107 Calc. 48.6 2.8 3.5 Found. 48.5 2.8 3.4 83 2-Cl-4-CF3-phenoxy CH3 H H 132-134 Calc. 55.6 3.3 3.1 Found. 55.6 3.3 3.1 84 2-Cl-4-CF3-phenoxy n-C4H9 H H 103-104 Calc. 58.1 4.2 2.8 Found. 58.3 4.4 2.9 85 2-Cl-4-CF3-phenoxy n-C5H11 H H 98-100 Calc. 58.9 4.5 2.7 Found. 58.7 4.5 2.7 86 2-Cl-4-CF3-phenoxy -CH(CH3)CH2CH2CH3 H H 89-915 Calc. 58.9 4.5 2.7 Found. 58.6 4.6 2.7 87 2-Cl-4-CF3-phenoxy -CH2CH2CH(CH3)2 H H not Calc. 58.9 4.5 2.7 isolated Found. Table 3 (continued) Example Analysis % NO. T R U V m.p. ( C) C H N 88 2-Cl-4-CF3-phenoxy -(CH2)9CH3 H H 92-95 Calc. 62.1 5.7 2.4 Found. 62.2 5.9 2.3 89 2-Cl-4-CF3-phenoxy -(CH2)13CH3 H H 101-103 Calc. 64.2 6.5 2.2 Found. 64.6 6.3 2.1 90 2-Cl-4-CF3-phenoxy -(CH2)15CH3 H H 98-100 Calc. 65.1 6.8 2.1 Found. 65.0 7.1 2.0 91 2-Cl-4-CF3-phenoxy cyclohexyl H H 138-140 Calc. 59.8 4.4 2.7 Found. 59.9 4.5 2.6 92 2-Cl-4-CF3-phenoxy phenyl H H 114-116 Calc. 61.2 3.6 2.6 Found. 61.7 3.7 2.6 93 2-Cl-4-CF3-phenoxy phenyl H H 128-130 Calc. 60.5 3.3 2.7 Found. 60.4 3.3 2.7 94 2-Cl-4-CF3-phenoxy -CH(CH3)CO2C2H5 H H 109-111 Calc. 55.6 3.9 2.6 Found. 55.6 4.0 2.6 95 2-Cl-4-CF3-phenoxy -CH2CO2C2H5 H H 119-121 Calc. 54.8 3.6 2.7 Found. 55.0 3.7 2.7 Table 3 (continued) Example Analysis % NO. T R U V m.p. ( C) C H N 96 2-Cl-4-CF3-phenoxy 2-tetrahydrofurylmethyl H H 124-126 Calc. 57.3 4.0 2.7 Found. 57.3 4.1 2.7 97 Cl n-C3H7 H H 102-104 Calc. 59.7 5.0 4.4 Found. 59.8 4.9 4.4 98 Cl Sec-C4H9 H H 90-93 Calc. 60.8 5.4 4.2 Found. 60.6 5.5 4.2 99 2-Cl-4-CF3-phenoxy -CH2CH2OCH3 H H 107-108 Calc. 55.5 3.8 2.8 Found. 55.6 3.9 2.9 100 2-Cl-4-CF3-phenoxy -CH2CH2OC2H5 H H 103-104 Calc. 56.3 4.1 2.7 Found. 55.6 3.9 2.9 101 2-Cl-4-CF3-phenoxy -(CH2CH2O)2CH3 H H 106-108 Calc. 55.4 4.2 2.6 Found. 55.5 4.3 2.6 102 2-Cl-4-CF3-phenoxy -(CH2CH2O)2C2H5 H H 86-88 Calc. 56.2 4.5 2.5 Found. 55.9 4.5 2.6 103 3-Cl-4-CN-phenoxy n-C3H7 Cl Cl 97-100 Calc. 54.4 3.3 5.5 Found. 54.4 3.3 5.1 Table 3 (continued) Example Analysis % NO. T R U V m.p. ( C) C H N 104 3-Cl-4-CN-phenoxy Sec-C4H9 Cl Cl 103-105 Calc. 55.2 3.6 5.4 Found. 55.6 3.8 5.0 105 4-CN-phenoxy n-C3H7 Cl H 68-70 Calc. 62.9 4.3 6.4 Found. 62.1 4.4 6.1 106 4-CN-phenoxy Sec-C4H9 Cl H 77-79 Calc. 63.7 4.6 6.2 Found. 62.9 4.8 6.0 107 4-NO2-phenoxy n-C3H7 Cl Cl 85-87 Calc. 53.5 3.7 5.7 Found. 53.6 3.7 5.8 108 3,5-dichloro-2-pyridyloxy Sec-C4H7 Cl H 116-118 Calc. 53.1 3.8 5.6 Found. 53.0 3.56 5.6 109 3,5-dichloro-2-pyridyloxy n-C3H7 Cl H 141-143 Calc. 52.1 3.5 5.8 Found. 52.0 3.4 5.7 110 3,5-dichloro-2-pyridyloxy Sec-C4H9 Cl Cl 78-80 Calc. 49.6 3.4 5.3 Found. 50.5 3.3 5.0 111 3,5-dichloro-2-pyridyloxy n-C3H7 Cl Cl 153-155 Calc. 48.6 3.1 5.4 Found. 47.8 3.0 5.3 Table 3 (continued) Example Analysis % NO. T R U V m.p. ( C) C H N 112 4-NO2-phenoxy Sec-C4H9 Cl Cl 131-133 Calc. 54.4 3.9 5.5 Found. 54.5 3.9 5.5 113 4-NO2-phenoxy n-C5H11 Cl Cl 132-134 Calc. 55.3 4.2 5.4 Found. 55.3 4.1 5.4 114 4-NO2-phenoxy n-C4H9 Cl Cl 129-130 Calc. 54.4 3.9 5.5 Found. 54.9 4.0 5.5

Claims: CLAIMS 1. A benzoylurea Found of fornila:- EMI34.1 in which each of P and Q independently represents a halogen atan or an alkyl group; m represents 0, 1 or 2; R represents an optionally-substituted alkyl, alkenyl, alkynyl, cycloalkyl or phenyl group, a hydrogen atom, one equivalent of an alkali metal or alkaline earth metal, or an ammonium or substituted ammonium group; each X independently represents a halogen atom, a cyano, nitro or carboxy group, or an optionally-substituted alkyl, alkoxy alkylthio, cycloalkyl, cycloalkyloxy, cycloalkylthio, alkenyl, alkenylthio, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, alkynyl, phenyl, phenoxy, phenylthio or amino group; q = 0, 1, 2, 3 or 4; T represents a halogen atom, at alkyl, haloalkyl, alkoxy, haloalkoxy, alkenyloxy or haloalkenyloxy group, or a phenoxy or pyridyloxy group optionally substituted by one or m:re substituents selected fran halogen atoms and nitro, alkyl, haloalRyl and cyano groups; each Y independently represents a halogen atan or a nitro, cyano, alkyl or haloalkyl group; and p = 0, 1, 2, 3 or 4. 2. A compound as claimed in claim 1, in which each of P and 0 independently represents a C(1-4) alkyl group or a fluorine, chlorine or branine atom, and m is O or 1. 3. A ocopund as claimed in either claim 1 or claim 2, in which T represents a bromine, fluorine or chlorine atom; a C(1-4) alkyl, haloalkyl or haloalkoxy group; an optionally substituted phenoxy group in which the optional substituents are selected fran l C(1-4) alkyl and haloaltyl groups, fluorine and chlorine atoms, and nitro and cyano groups; or an optionally substituted pyridyloxy group in which the optional substituents are selected fran trifluoromethyl groups and fluorine and chlorine atoms. 4. A compound as claimed in any one of claims 1 to 3, in which T represents an optionally substituted 2-pyridyloxy group in which the optional substitutents are selected fran halogen atoms and haloalkyl groups, or T represents a 2-chloro-4-trifluoromethylphenoxy, 2-fluoro-4-trifluoro methylphenoxy or 2-cyano-4-trifluoromethylphenoxy group. 5. A compound as claimed in any one of claims 1 to 4 in which Y represents a fluorine, chlorine or bromine atom, a C(1-4) alkyl or haloalkyl group, or a nitro or cyano group, and p is 0, 1 or 2. 6. A ccttpound as claimed in any one of claims 1 to 5, in which X represents a branine, chlorine or fluorine atan or a C(l-4)alkyl group, and q is O or 1. 7. A compound as claimed in any one of claims 1 to 6, in which R represents an optionally substituted alkyl group containing 1 to 20 carbon atoms, a C(3-6) cycloalkyl group, or an optionally substituted phenyl group, the substituents in the optionally substituted phenyl group being selected fram C(1-4) alkyl and haloalkyl groups, nitro and cyano groups, and halogen atoms, and the substituents in an optionally substituted alkyl group being selected fran halogen atoms, C(1-4) alkoxy groups, carboxy groups, alkoxycarbonyl groups containing 2 to 5 carbon atoms, groups of formula -O-(Ch2Ch2O)nalkyl where n is 1 to 4, and the alkyl rt: :oiety has 1 to 4 carbon atoms, optionally substituted phenyl groups in which the optional substituents are as gin above for an optionally substituted phenyl group R, and heterocyclic groups. 8. A compound as claimed in claim 7, in which R represents an unsubstituted alkyl group having from 1 to 10 carbon atoms. 9. A carpound as claimed in any one of claims 1 to 6, in which R represents a group of general formula -(CH2Ch2O)nRÚ in which RÚ represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or phenyl group, and n represents 1,2,3,4 or 5. 10. A compound as claimed in claim 9, in which R represents an alkyl or haloalkyl group containing 1 to 10 carbon atoms, the halogen being chlorine or fluorine, and n is 1 or 2. 11. A compound as claimed in any one of claims 1 to 10, in which the -COOR group is located in the 2 position of the phenyl group to which it is attached. 12. A compound as claimed in claim 1, and named in any one of Exaples 1 to 63 wherein. 13. A process for preparing a compound as claimed in any one of claims 1 to 12, which canprises reacting a benzoyl isocyanate of formula: EMI36.1 with a sulphenamide of formula: EMI37.1 in which P, Q, m, R, X, q, T, Y and p have the meanings given in any one of claims 1 to 11. 14. A process as claimed in claim 13, in which the reaction temperature is in the range of from 0 to 1000C. 15. A process as claimed in claim 13, carried out substantially as described in any one of Examples 1 to 4 herein. 16. A copond of the general formula TV given in claim 13, in which P, Q, m, R, X, q, T, Y and p have the treanings given in any one of Claims 1 to 11. 17. A ccpnpcernd as claimed in claim 16 and named in any one of Examples 65 to 114 herein. 18. A process for the preparation of a compound as claimed in claim 16, which comprises reacting a sulphenyl halide of formula: EMI37.2 wherein X, q and R have the meanings given in Claim 16 and Hal represents a halogen atan, with an aniline of formula: EMI37.3 wherein T, Y and p have the meanings given in Claim 16 in the presence of a dehydrohalogenating agent. 19. A pesticidal composition which comprises a compound as claimed in any one of claims 1 to 12, together with a carrier 20. A composition as claimed in claim 19, which comprises at least two carriers, at least one of which is a surface-active agent. 21. A method of combating pests at a locus, which comprises applying an insecticidally effective arount of a compound as claimed in any one of claims 1 to 12 or a composition as claimed in either claim 19 or claim 20 to the locus.

Inventors: ANDERSON, MARTIN
Applicants: SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.
Application year: 1983
Main classification: C07C145
IPC codes: C07D213, C07D307, C07C313, A01N47