Title of Invention

"A HERBICIDAL COMPOSITION"

Abstract

. HERBICIDAL COMPOSITION" A herbicidal composition comprising: (a) a urea herbicide, having the general formula (I):- R11N(R12)CON(R13)R14 (I)wherein R11 represents a cyclic hydrocarbyl (e.g. phenyl) or aromatic heterocyclyl (e.g. thiadiazol-2-yl) group, wherein the cyclic hydrocarbyl or aromatic heterocyclyl group is optionally substituted as herein described, R12 represents hydrogen or straight or branched chain alkyl oontaining from 1 to 6 carbon atoms, R13 represents straight or branched chain alkyl containing from 1 to 6 carbon atoms or an optionally substituted cyclic hydrocarbyl (e.g. 2-methyIcyclohexyl) group, wherein the cyclic hydrocarbyl group is optionally substituted as herein described, and R14 represents hydrogen or straight or branched chain alkyl or alkoxy containing from 1 to 6 carbon atoms; with the exception of diuron (3-(3,4-dichlorophenyl)-1,1 -dimethylurea); and (b) a 4-benzoylisoxazole herbicide or a 2-cyano-1,3-dione herbicide; an enoiic tautomeric form thereof, or an agriculturally acceptable salt or metal complex thereof of the kind such as herein described; which are herbicidally effective in combination, in association with an agriculturally acceptable diluent and/or carrier of the kind such as herein described, and wherein the herbicidal composition contains from 0.05 to 90% by weight of (a) and (b).

Full Text

The present invention relates to a herbicidal composition. This invention relates to new herbicidal compositions comprising a mixture of 4-benzoylisoxazoles or 2-eyano-l,3-diones and bencidical urea compounds. It also relates to the use of the mixture per se and to a method of controlling weeds. Herbicidal 4-benzoylisoxazoIes as disclosed in the literature, for Example see European Patent Publication Nos. 0418173, 0487337, 0527036 and 0560482. Herbicidal 2-cyano-l,3-dione derivatives are known from EP213892, EP469630, EP469631 and EP560482. The first commercially available 4-benzoylisoxazole is isoxaflutole [5-cyclopropyl-4-(2-methylsulphonyl-4-trifluoromethyl)-benzoylisoxazole]. Urea herbicides are well known in the literature. Examples of such herbicides include fenuron, fluometuron, monuron and monolinuron, chlortoluron, isoproturon, diuron,linuron, neburon, methabenzthiazuron and tebuthiuon, alll of which are described in the Pesticide Manual 10th edition (British Crop Protection Council). The present invention provides a method for controlling the growth of weeds (i.e. undesired vegetation) at a locus which comprises applying to the locus an effective amount of (a) a urea herbicide, preferably a compound of the general formula (I):- (Formula Removed) wherein R11 represents an optionally substituted cyclic hydrocarbyl (which is preferably aromatic e.g. phenyl) or aromatic heterocyclyl (e.g. thiadiazol-2-yI) group, R12 represents hydrogen or straight or branched chain alkyl containing from 1 to 6 carbon atoms, R.13 represents straight or touched chain alkyl containing from 1 to 6 carbon atoms or an optionally substituted cyclic hydrocarbyl (e.g. 2-methylcyclohexyl) group and R14 represents hydrogen or straight or branched chain alkyl or alkoxy containing from 1 to 6 carbon atoms; and (b) a 4-benzoylisoxazole herbicide or a 2-cyano-l,3-dione herbicidepn enolic tautomeric form thereof, or an agriculturally acceptable salt or metal complex thereof, which are herbicidally effective in combination, For this purpose, the urea herbicide and (b) are normally used in the form of herbicidal eompasWan* (U, ill AUdUAtiOii with wuipuUblc diluuntii or carriers and/or surface-active ageoti suitable fnr use in hfirhtairtol nnmposirions), for example as hereinafter dtfcribfd. Preferred compounds of general formula I are those wherein R12 represents the hydrogen atom or the methyl group and R13 represents the methyl group, Preferred compounds of general formula I are those wherein R12 represents the hydrogen atom, R13 represents a phenyl, 3-trifluoromethylphanyl or 4-chlorophenyl group and R14 represents the methyl group; or (b) R* 1 represents a 4-chlorophenyl group and R14 represents the metfaoxy group, which are known respectively as fenuron, fluometuron, monuron and monolinuran, and more especially compounds of general formula I wherein R12 represents the hydrogen atom and R13 represents the methyl group and (c) R11 represents a 3- chloro-4-methylphenyl or 4-isopropylphenyI group and R^ represents the methyl group; or (d) R1! represents the 3,4-dichlorophenyl group and R14 represents methyl, methoxy or butyl; or (e) Ru represents the benzothiazol-2-yl group, R1Z represents methyl and R13 represents methyl and R14 represents hydrogen or (f) Ru represents 5-t-butyI- thiadjazol-2-yl; R12 and R13 represent methyl and R14 represents hydrogen; which are known respectively as chlortoluron, isoproturon, diuron, linuron, nebuvon, mothatonzthiozuron and tebuthiuron. Preferably (a) is tebuthiuron. Preferably (b) is a 4-benzoylisoxazole herbicide. Preferably the 4-benzoylisoxaznle has the formula (TT): (Figure Removed) wherein wherein R is hydrogen or -CO2R3; R1 is Ci>4 alkyl or €3.5 cycloalkyl optionally substituted by €1.5 alkyl; R2 is selected from halogen, nitro, cyano, -(CR4R5)qS(0)pR6, -S(0)pR6, -N(R7)S02R6 Ci_6 alkoxy, -OSC^R6, CM haloalkoxy, CM alkyl and Ci_4 haloalkyl, wherein R4, R5, R6, R?, p and q are as defined below; or two groups R2, on adjacent carbon atoms of the phenyl ring may, together with the carbon atoms to which they are attached, form a 5 or 6 membered saturated or unsaturated heterocyclic ring containing up to three ring heteroatoms selected from nitrogen, oxygen and sulfur, which ring may be optionally substituted by one or more groups selected from halogen, nitro, -S(0)pR6, C^ alkyl, C^ alkoxy, C^ haloalkyl and GI_4 haloalkoxy, wherein R^ and p are as defined below, it being understood that a sulphur atom, where present in the ring, may be in the form of a group -SO- or -SO2S n is an int*g«r froai oat to five; p is BOVO» one or two; q is ens or two; whti* 4 Ii Lwu ihc yn;up» (CR^R^) mwy be me same or different; R3 is Cj.4 alkyl; R4 and R^ are independently hydrogen or Cj_4 alkyl; R6 i« €1,4 alkyl, or phenyl or benzyl, each of phenyl and benzyl optionally bearing from one to five substituents which may be the same or different selected from the group consisting of halogen, C\^ alkyl, CM alkoxy, C^ haloalkyl, Ci_4 haloalkoxy, nitro and -S(0)pCH3, wlioiciii p in MS defined above; and R7 is hydrogen or Cj_6 alkyl. In this description the term "agriculturally acceptable salts" means salts the cations of which are known and accepted in the art for the formation of salts for agricultural or horticultural use. Preferably the salts are water-soluble. Suitable salts with bases include alkxli metal (e.g. sodium and potassium), alkaline earth metal (e.g. calcium and magnesium), ammonium and amine (e.g. dietfaanolamine, tricthaoolamJBft, oetylamuw, nwrphelinc ami diwtylmethyUmuw) Mlti, It will be understood that in certain cases the groups R1, R2, R3, R4, R5, R6 and R7 may give rise to stereoisomers and geometric isomers. All such forms are embraced by the present invention. Throughout this description the terms "alkyl" and "alkoxy" refer to ttUwlyk ur branched chains, me terms "naloalkyl" and "haloalkoxy" refer to alkyl and alkoxy reapectively, each substituted by at least one halogen. Hie term "halogen" refers to fluorine, chlorine, bromine and iedne. In formula (II) above, compounds in which n is three and the groups (R\ occupy the 2,3 and 4-positions of the benzoyl ring; or in whioh ft io two and the groups (R^)n eeeupy the 2 and 4- positions of the benzoyl ring are preferred. In formula (II) above, R2 is preferably selected from halogen (preferably chlorine or bromine), -S(0)pMe and trifluoromethyl. In formula (II) above, preferably one of the groups R2 is •S(0)pMe. Compounds of formula (II) above in which R is hydrogen are also preferred. Tht compound! of formula (II) of particular interfifit include the following: 5"Cyclopropyl-4-(2-methylsulphonyl-4-trifluoromethyl)benzoyli»oxazole (isoxaflutole); 5-cyclopropyl-4-{4-methylsulphonyl-2-trifluoromethyl)benzoylisoxazole; 4-(2-chloro-4-methylsulphonyl)ben2oyl-5-cyclopropylisoxazole;4-(4-chloro-2-methylsulphonyl)benioyl-5-cyclopropyUsoxazole;4-(4-bromo-2-methyliulphonyl)benzoyl-5-cyclopropylisoxazole; and ethyl S^yclopropyW^-methyJbwlphonyM-trifluoromethyl)benzoylisoxazole-3-carboxylate. When component (b) is a 2-cyano-l,3-dione derivative, it is Bwurally a aompound of fbimulo (III) i (Figure Removed) wherein R3U is C^ alkyl or C^ cycloalkyl optionally substituted by C^ alkyl; is selected from halogen, nitro, cyano, -S(O)rR32| Ci^ alkoxy, -OSO2R32, hdoalkyl; or two groups R3 1, on adjacent carbon atoms of the phenyl ring may, together with the carbon atoms to which they are attached, form a 5 or 6 numbered satUi'ftUid 6i' uaidlumtcd liclcmvyulic ring contaiiung up to three ring heteroatoms selected from nitrogen, oxygen and sulfur, which ring may be optionally substituted by one or more groups selected from halogen, nitro, -S(0)iR32, Ci_4 alkyl, Ci_4 alkoxy, Cj^ haloallcyl and C^ haloalkoxy, it being understood that a sulphur atom, where present in the ring, may be in the fonn of a group -SO- or -S02S t is an integer from one to five (preferably one, two or three); r is zero, one or two; R.32 is Cm alkyl, or phenyl or benzyl, each of phenyl and benzyl optionally bearing from one to five substituents which may be the same or different selected ft*m ihe-fmup-oansisting of halogen, Cj^ ilkjl, CM alkoxy, C\^ haloalkyl, Ci4 haloalkoxy, nitro and -S(O)rCH3; 1_(t v is one or two; where v is two the groups (CR33R34) j^y ^ me same or different; an enolic tautomeric form thereof, or an agriculturally acceptable salt or metal complex thereof. It will be understood that the compounds of formula (HI) may nvist in enolic. tautomeric forms that may give rise to geometric Uomers around the enolic double bond. Furthermore, in certain cases the groups R30 to R32 may give rise to stenoisomers and geometric isomers. All such forms are embraced by the present invention. By the term "metal complexes" is meant compounds in which one or both of the oxygen atoms forming part oft 1,3-dione in formula (II) act as ohelating agents to a metal cation. Examples of such cations include zinc, manganese, cupric, cuprous, ferric, ferrous, titanium and aluminium. It will be understood that hi the description that follows, reference to compounds of formula (II) includes agriculturally acceptable salts, metal complexes or enolic tautomeric forms thereof. R30 is preferably 1-methylcyclopropyi or, most preferably cyclopropyl is preferably selected from halogen (preferably chlorine or bromine), -8(0)^6, trifluoromethyl, C^ haloalkoxy, C\^ alkoxy and Preferably t is two or three, Compounds of formula (III) in which either t is three and the groups (R31)t occupy the 2,3 and 4-positions of the benxoyl ring; or in which t ii two and the groups (R.3 1\ occupy the 2 and 4- positions of the benzoyl ring; are preferred. Preferably one of the groups R31 is -S(0)rMe. Compounds of formula (III) of particular interest include 3-cyclopropyl-2-cyano-l -2H3yano-3-cyclopropylpropan-l,3-dione; 23-dione; 2-cyanol-(4-methylsulphonyl"2-tiifluoromethylphenyl>3« (l-methylcyclopropyl)propan-l^-dione; and l-(4-chloro-2-methylsulphonylphenyl)-2-cyano-3-cyclopropylpropan- 1 ,3-dione. Most preferably the compound of formula (HI) is 2-cyano-3-cyclopropyl-1 -(4-fluoK>-3-methoxy-2-methyLiulphonylphenyl)propan-l ,3-dione. The amounts of the urea herbicide and (b) applied vary with the nature of the weeds, the compositions used, the time of application, the climatic and edaphic conditions and (when used to control the growth of weeds in crop-growing areas) the nature of the crops. When applied to a crop-growing area, the rate of application should be sufficient to control the growth of weeds without causing substantial permanent damage to the crop. In general, taking these factors into account, application rates of from about 500 g and 2500 g of the urea herbicide and from about 10 g to about 500 g of (b) per hectare give good results. However, it is to be understood that higher or lower application rates may be used, depending upon the particular problem of weed control encountered. The urea herbicide and (b) in combination may be used to control selectively the growth of weeds, for example to control the growth of those species hereinafter mentioned, by pro- or post- emergence application in a directional or non-directional fashion, e.g. by directional or non-directional spraying, to a locus of weed infestation which is an area used, or to be used, for growing crops, for example cereals, e.g. wheat, barley, oats, rye, maize and rice, soya beans, field and dwarf beans, peas, lucerne, cotton, peanuts, flax, onions, carrots, oilseed rape, sunflower, and permanent or sown grassland before or after sowing of the crop or before or after emergence of the crop. For the selective control of weeds at a locus of weed infestation which is an area used, or to be used, for the growing of crops, e.g. the crops hereinbefore mentioned, application rates of from about 500 g to about 2500 g of the urea herbicide and from about 25 g to about 200 g of (b) per hectare are particularly suitable. The method described above may be used to control a very wide spectrum of annual broad-leafed weeds and grass weeds. Examples of weeds which may be controlled include: broad-leafed weeds, for example, Abutilon theonhrastL t retroflexuj. AlflflflTinltlUB FUdtfi Amaranthus tiiberoulatos. Ambrosia ftrtcniisiifblia. Ambrosia tpfida, Bidena PJlogftr ChCBOPP^*um frlhm". Convolvulus arvensis. Datura ferox. Datura stramonium. Euphorbia spp. Qa|hjfl ap^p'^e spp. Ipomoeaipp. e.g. Inomoea purpurea. Laarium spp. MfltriPflTl? Polvaomim raphjini«tnim Sohlnihrty pjnfl^f , Seahaa^ tfffillfflP' Sida_spinosa_ Sjnat}is arycinsis. SolflffliilP T^'grm^- Veronica Veronica persioa. and Xanthiujiti fftrwr>'lim and grass weeds, for example Alopecurm roypjujflidfig, A vena Btachiaria olantattinea. CenohruB echinatus. > Dicitaria tuuizontftlia Hioitiirtii tn Panicum bicolor. Elcusine indica. Imoerata miliaceum. Pennisetum glaucum. Sotaria spp. e.g. Setaria faberii. viridjg. Setaria lutesoens and Solaria italioa. Sorghum halepense. and sedges, for example, Cvperus esculentus. Where the locus is an area used, or to be used, for the growth of cereal crop preferably the urea herbicide is isoproturon or chlorotoluron. Where the locus is an area used, or to be used, for the growth of sugarcane, or for total weed control, the urea herbicide is preferably tebuthiuron. The following table summarizes dose rate of the components generally and preferably in the method of the invention (all dose rates are in grammes per hectare (g/ha): (Table Removed) Where the method of the invention is used for the control of weeds at a cereal locus in a preferred embodiment (especially where (a) is isoproturon or chlortoluron) a third herbicide is provided, preferably selected from bifenox, diflufonican. When the locus is sugarcane (especially where (a) is tcbuthiuron) preferred third partners include diuron and ametrvne.Freferred combinations include the following: (i) from 1000 to 1500g/ha of (a) (preferably from 1400 to 1500g/ha); from 50 to 7Sg/ha of (b) and from 100 to ISOg/ha of diflufenican; (ii) from 1000 to 1500g/ha of (a) (preferably about lOOOg/ha); from SO to 75g/hat>f (b) and from 100 to ISOg/ha of diflufenioan; (iii) from 1 OOOg/ha of (a); from 100 to 1 SOg/ha of (b); and from 1000 to 1 SOOg/ha (preferably about 1250g/ha) of diuron or ametryne. Tho invention oloo providoo ovntfgiotio horbioidol oompooitiono comprising: (a) a urea herbicide, preferably a compound of the general formula (I) above; and (b) a 4-benzoylisoxazole herbicide or a 2-cyano-l,3-dione herbicidejan enolic tautomeric form thereof, or an agriculturally acceptable salt or metal complex thereof; in association with an agriculturally acceptable diluent and/or carrier. Generally the active ingredients are homogeneously dispersed in other components cited hereinafter, such as a diluent or carrier and/or surface-active agents. The term "herbicidal compositions" is used in a broad sense, to include not only compositions which are ready for use as herbicides but also concentrates which must be diluted before use. Preferably the composition* contain from O.OS to 90% by weight of (a) and (b). Hie herbicidal composition may contain solid and liquid carriers and surface-active agents (e.g. welters, dispenants or emulsifiers alone or in combination). Surface-active agents that may be present in the herbicidal compositions of the present invention may be of the ionic or non-ionic types, for example sulphoricinoleates, quaternary ammonium derivatives, products based on condensates of ethylene oxide with nonyl- or octyl-phenols, or carboxylic acid esters of anhydrosorbitols which have been rendered soluble by etherification of the free hydroxy groups by condensation with ethylene oxide, alkali and alkaline earth metal salts of sulphuric acid esters and sulphonic acids such as dii»nyl-and dioctyl-sodium sulphono-succinates and alkali and alkaline earth metal salts of high molecular weight sulphonic acid derivatives such as sodium and calcium lignosulphonates. Examples of suitable solid diluents or carriers'are aluminium silicate, talc, calcined magnesia, kieselguhr, uicalcium phosphate, powdered cork, absorbent carbon black and clays such as kaolin and bentonite. Examples of suitable liquid diluents include water, acetophenone, cyclohexanone, isophorone, toluene, xylene, and mineral, animal, and vegetable oils (these diluents may be used alone or in combination). Herbicidal compositions according to the present invention may also contain, if desired, conventional adjuvants such as adhesives, protective colloids, thickeners, penetrating agents, stabilisers, sequestering agents, anti-caldng agents, colouring agents and corrosion inhibitors. These adjuvants may also serve as carriers or diluents. Preferred herbicidal compositions according to the present invention are wettable powders or water dispersible granules. Most preferred herbicidal compositions are aqueous suspension concentrates. The wettable powders (or powders for spraying) usually contain from 20 to 95% of combination, and they usually contain, in addition to the solid vehicle, from 0 to 5% of a wetting agent, from 3 to 10% of a dispersant agent and if necessary, from 0 to 10% of one or more stabilisers and/or other additives such as penetrating agents, adhesives or anti-caking agents and colourings. The aqueous suspension concentrates, which are applicable by spraying, are prepared in such a way as to obtain a stable fluid product (by fine grinding) which does not settle out and they usually contain from 10 to 75% of combination, from 0.5 to 15% of surface acting agents, from 0.1 to 10% of thixotropic agents, from 0 to 10% of suitable additives such as antifoams, corrosion inhibitors, stabilisers, and water or an organic liquid in which the active substance is sparingly soluble or insoluble. Some organic solid substances or inorganic salts can be dissolved in order to assist in preventing sedimentation or as antifreeze for the water, Herbicidal compositions according to the present invention may also comprise (a) and (b) in association with, and preferably homogeneously dispersed in, one or more other pesticidally active compounds and, if desired one or more compatible pesticidally acceptable diluents and carriers. Examples of other pesticidally active ingredients include fungicides, insecticides, plant growth regulators and, most preferably, herbicides. Examples of additional herbicides which may be present include the following (a mixture of urea herbicides may be used in the invention): chloroacetamides (e.g. metolachlor, acetochlor, alachlor), sulfonylureas, fhiocarbamates, dithiocarbamates, metribuzin, sulfentrazone, flumetsulam, clorasulam-methyl, oxasulfuron, flumiclorac, bentazon, chlorimuron, linuron, clomazone, dimethenamid, pendimethalin, trifluralin, clethodim and acifluorfen, bifenox, difluftnican, diuron, atrazine and ametryne. The following examples illustrate the invention without limiting it. Example 1 The following tost was conducted in Brazil. Tebuthiuron (used as the commercial formulation "Combine™", a suspension concentrate containing 1,01/ha active ingredient) and 5-cyclopropyl-4-(2-methylsulphonyl-4-trifluoromethyl)benzoylisoxazole (isoxaflutole, hereafter referred to as Compound A), which was formulated as a wcttable granules, were sprayed alone and in tank mix combination (spray rate 3001/ha) to a plot 5 metres by 3 metres pro-emergence of the weeds and ratoon sugarcane (varieties RB72 454 and RB83 5089). The soil was a heavy clay soil containing 1.8% organic matter, 69% sand and 28% clay (ph 5.3) and had been sown on the same day as application with the weed tpeeies (the application was made to the ratoon cane about 90 days after cutting and before re-growth). Visual assessment was made 95 days after treatment in comparison with an untreated control plot Two replicates were performed. The results were as follows (in the Table that follows the weed and crops are represented by their Bayer codes): (Table Removed) Eumple 2 The following teit was conducted in Brazil following the same procedure as described in Example 1 above but where the soil type was light sandy containing 1.8% organic matter, 82% sand and 13% clay (ph 5.3). Again, two replicates were performed. The results were as follows (in the Table that follows the weed and crops are represented by their Bayer codes): (Table Removed) WE CLAIM: 1, A herbicidal composition comprising: (a) a urea herbicide, having the general formula (I):- (Formula Removed) wherein R11 represents a cyclic hydrocarbyl (e.g. phenyl) or aromatic heterocyclyl (e.g. thiadiazol-2-yl) group, wherein the cyclic hydrocarbyl or aromatic heterocyclyl group is optionally substituted as herein described, R12 represents hydrogen or straight or branched chain alkyl containing from 1 to 6 carbon atoms, R13 represents straight or branched chain alkyl containing from 1 to 6 carbon atoms or an optionally substituted cyclic hydrocarbyl (e.g. 2-methylcyclohexyl) group, wherein the cyclic hydrocarbyl group is optionally substituted as herein described, and R14 represents hydrogen or straight or branched chain alkyl or alkoxy containing from 1 to 6 carbon atoms; with the exception of diuron (3-(3,4-dichlorophenyl)-1,1-ditnethylurea); and (b) a 4-benzoylisoxazole herbicide; an enolic tautomeric form thereof, or an agriculturally acceptable salt or metal complex thereof of the kind such as herein described; which are herbicidally effective in combination, in association with an agriculturally acceptable diluent and/or carrier of the kind such as herein described, and wherein the herbicidal composition contains from 0.05 to 90% by weight of (a) and (b). 2. A composition as claimed in claim 1 in which compounds of general formula 1 are those wherein R12 represents the hydrogen atom or the methyl group and R13 represents phenyl or a methyl or a 3-trifluoromethylphenyl or 4-chlorophenyl and R14 represents the methyl group. 3. A composition as claimed in claim 1 in which compounds of general formula (I) are those wherein R11 represents a 4-chIorophenyl group or a 3-chloro-4- methylpheny] or 3,4-dichlorophenyl or 4-isopropylphenyl and R14 represents a methyl or methoxy or butyl group. 4, A composition as claimed in claim 1 in which compounds of formula (I) are those wherein R11 represents the benzothiazol-2-y] group, or a S-t-bulyl- thiadiazol-2-yl; R12 and R13 represent methyl and R14 represents hydrogen. 5. A composition as claimed in claim 1 in which (a) is I-{5-tert-butyl- l,3,4-thiadiazol-2-yl)-l,3-dimethylurea. 6, A composition as claimed in claim 1 in which (b) is a 4- benzoylisoxazole herbicide of formula (11): (Formula Removed)wherein R is hydrogen or -CO2R3; R1is C1-4 alkyl or C3-6 cycloalkyl optionally substituted by C1-6 alkyl; R2is selected from halogen, nitro, cyano, -(CR4R5)qS(0)pR6, -S{0)pR6, -N(R7)S02R6, C1-6 alkoxy, -OSO2R6, C1-4haloalkoxy, C1-4 alkyl and C1-4 haloalkyl, wherein R4, R5, R6, R7, p and q are as defined below; or two groups R2, on adjacent carbon atoms ofthe phenyl ring may, together with the carbon atoms to which they are attached, form a 5 or 6 membered saturated or unsaturated heterocyclic ring containing up to three ring heteroatoms selected from nitrogen, oxygen and sulfur, which ring may be optionally substituted by one or more groups selected from halogen, nitro, -S(0)pR6, C1-4 alkyl, C1-4 alkoxy, C1-4haloalkyl and C1-4 haloalkoxy, wherein R6 and p are as defined below, it being understood that a sulphur atom, where present in the ring, may be in the form of a group -SO or -SO2-; n is an integer from one to five; p is zero, one or two; q is one or two; where q is two the groups (CR4R5) are the same or different; R3 is C1-4 alkyl; R4 and R5 are independently hydrogen or C1-4 alkyl; R6 is C1-4 alkyl, or phenyl or benzyl, each of phenyl and benzyl optionally bearing from one to five substituents which may be the same or different selected from the group consisting of halogen, C1-4 alkyl, C1-4 alkoxy, C1-4haloalkyl, C1-4 haloalkoxy, nitro and -S(0)2,CH3, wherein p is as defined above; and R7 is hydrogen or C1-6 alkyl. 7. A composition as claimed in claim 6 in which n is two or three and the groups (R2)n occupy the 2,3 and 4-positions of the benzoyl ring. 8. A composition as claimed in claim 6 in which R2 is preferably halogen (preferably chlorine or bromine), -S(0)pMe and trifluoromethyL 9. A composition as claimed in claim 8 in which one of the groups R- is -S(0)pMe. 10. A composition as claimed in claim 6 in which R is hydrogen. 11. A composition as claimed in claim 6 in which (b) is 5-cyclopropyl-4-(2-methylsulphonyl-4-trifluoromethyl)benzoylisoxazole(isoxaflutole); 5-cyclopropyl-4-(4-methylsulphonyl-2-trifluoromethyl)benzoylisoxazole; 4-(2-chloro-4-methylsulphonyl)benzoyl-5-cyclopropylisoxazolc; 4-(4-chloro-2-methylsulphonyl)benzoyl-5-cyclopropylisoxazole; 4-(4-bromo-2-methylsulphonyl)benzoyl-5-cyclopropylisoxazole; and ethyl 5-cyclopropyl-4-{2-methylsulphonyl-4-trifluoromethyl)benzoylisoxazole-3-carboxylate, 12. A composition as claimed in claim 1 in which (b) is a 2-cyano-l,3-dione derivative of formula (III): wherein R30 is C1-4alkyl or 3-6 cycloalkyl optionally substituted by C1-6 alkyl; R31 is selected from halogen, nitro, cyano, -S(0),R32, -(CR33R34),S(0)1R32', -N(R35)S02R32, C1-6 alkoxy, -OSO2R32, C1-4 haloalkoxy, C1-4alkyl or C1-4 haloalkyl; or two groups R31, on adjacent carbon atoms of the phenyl ring may, together with the carbon atoms to which they are attached, form a 5 or 6 membered saturated or unsaturated heterocyclic ring containing up to three ring heteroatoms selected from nitrogen, oxygen and sulfur, which ring may be optionally substituted by one or more goups selected from halogen, nitro, -S(O)1R32,C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl and C1-4 haloalkoxy, it being understood that a sulphur atom, where present in the ring, may be in the form of a group -SO- or -SO2-; t is an integer from one to five (preferably one, two or three); r is zero, one or two; R32 is C1-4alkyl, or phenyl or benzyl, each of phenyl and benzyi optionally bearing from one to five substituents which may be the same or different selected from the group consisting of halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, C1-4 haloalkoxy, nitro and -S(0)1CH3; R33, R34 and R35 are independently hydrogen or C1-4 alkyl; v is one or two; where v is two the groups (CR33R34) may be the same or different; an enolic tautomeric form thereof, or an agriculturally acceptable salt or metal complex thereof. 13. A composition as claimed in claim 12 in which R30 is 1-methylcyclopropyI or cyclopropyl, and/or R31 is selected from halogen (preferably chlorine or bromine), -S(O),Me, trifluoromethyl, C1-4 haloalkoxy, C1-4alkoxy and -CH2S(0)1Me. 14. A composition as claimed in claim 12 in which t is two or three, and/or one of the groups R31 is -S(0)1Me. 15. A composition as claimed in claim 12 in which t is two or three and the groups (R31)1 occupy the 2,3 and 4-positions of the benzoyl ring, or the 2 and 4-positions of the benzoyl ring. 16. A composition as claimed in claim 12 in which (b) is 3-cyclopropyl-2-cyano-l-(2-methylsulphonyl-4-trifluororaethyipheny])propan-l,3-dione; 1 -(2-chIoro-4-methyIsulphonylphenyl)-2-cyano-3-cyclopropylpropan-l ,3-dione; 2-cyano-3-cyclopropyl-1 -(4-fluoro-3-methoxy-2-methylsulphonyIphenyl)propan-l,3-dione; 2-cyano-l-(4-methyIsulphonyl-2-trifluoromethylphenyl)-3-( l-methylcyclopropyl)propan-1,3-dione; and 1 -(4-chloro-2-methylsulphonylphenyl)-2-cyano-3-cyclopropylpropan-l ,3-dione; and/or the compound of formula (III) is 2-cyano-3-cyclopropyl-l-{4-fluoro-3-methoxy-2- m ethyl sulphonylplienyl)propan-1,3-dione. 17. A composition as claimed in any one of claims 1 to 16 substantially as hereibnbefore described.

Documents:

0376-del-1999-abstract.pdf

0376-del-1999-claims.pdf

0376-del-1999-complete specification (granted).pdf

0376-del-1999-correspondence-others.pdf

0376-del-1999-description (complete)-16-05-2008.pdf

0376-del-1999-description (complete).pdf

0376-del-1999-form-1.pdf

0376-del-1999-form-18.pdf

0376-del-1999-form-2.pdf

0376-del-1999-form-4.pdf

0376-del-1999-form-6.pdf

0376-del-1999-gpa.pdf

376-DEL-1999-Abstract-(15-10-2008).pdf

376-DEL-1999-Abstract-(16-05-2008).pdf

376-DEL-1999-Claims-(01-01-2009).pdf

376-DEL-1999-Claims-(15-10-2008).pdf

376-DEL-1999-Claims-(16-05-2008).pdf

376-DEL-1999-Correspondence-Others-(16-05-2008).pdf

376-DEL-1999-Correspondence-Others-(16-10-2008).pdf

376-DEL-1999-Form-1-(16-05-2008).pdf

376-DEL-1999-Form-2-(16-05-2008).pdf

376-DEL-1999-GPA-(15-10-2008).pdf

376-DEL-1999-GPA-(16-05-2008).pdf

376-DEL-1999-Petition-137-(16-05-2008).pdf

376-DEL-1999-Petition-138-(16-05-2008).pdf