Title of Invention

"HERBICIDAL SYNERGISTIC COMPOSITION COMPRISING TRIFLOXYSULFURON SODIUM AND METHOD OF WEED CONTROL"

Abstract

A herbicidal synergistic composition which comprises, in addition to conventional inert formulation adjuvants of the kind such as herein described, trifloxysulfuron sodium in admixture with a synergistically effective amount of a compound from the substance class of formula IV wherein n is 0 or 1, R6 is hydrogen, -CH2 or -NH2, R7 is hydroxy, C2H5, Na+, -CH(CH3)2-CO2 -CH=CH2 -C4H9-n or -CH2-CH2-O-N=C(CH3)2 and Q is the group

Full Text

the present invention relates to a novel herbicidal synergistic composition comprising a combination of herbicidal active ingredients, which composition is suitable for selective weed control in crops of useful plants, for example in crops of cereals, cotton, soybeans, sugar beet, sugar cane, plantations crops, rape, maize and rice. The invention further relates to a method of controlling weeds in crops of useful plants and to the use of the novel composition for that purpose. The compound of formula (Figure Removed) has herbicidal activity. The following compounds are also known as herbicides and some of them are also available commercially: compounds of formula II A-SO2-NH-E (II), (Figure Removed) are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, pages 549 and 49; (Figure Removed) wherein U-V is a group of the formula RiC=N, N=CRi, CONR1( R^CO or RiC=CR2, wherein RT is -NHCgHrflso), .NHC(CH3)2CN, -NHC4H9-(tert), -NHC2H5, (Figure Removed) W-Y is a group of the formula CR2=N, CONR2, NR2CO, CONRs or CR2=CR3, wherein R2 is methyl, -Cl, -NH2, -NHC3Hr(iso) or -NHCaHs and R3 is -NHCH3 or C4H9-(tert), and R is -Cl, -SCH3, -C4H9-(tert), methoxy, hydroxy, N(CH3)2, CHF2 or hydrogen; or U-V-W-Y together form the group -C(CF3)=C(R4)-C(CH2-C3H7-(iso))=C(R5)-, wherein R4 is (Figure Removed) are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, pages 32, 51, 565, 840, 740, 239, 956, 699, 959, 962, 974 and 375; compounds of formula IV (Figure Removed) wherein n is 0 or 1, Re is hydrogen, -CH3 or -NH2l R7 is hydroxy, CoHs, Na*. -CH(CH3)2-C02-CH=CH2, -C4H9-n or (Figure Removed) are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, pages 271, 888, 542, 541, 898, 441, 623, 471, 848 and 298, and from US-A-5183492; compounds of formula V (Figure Removed) 3-trifluoromethylphenyl or phenyl, R9 and RIO are each independently of the other hydrogen or methyl and (Figure Removed) are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, pages 376, 490, 947 and 975; compounds of formula VI (Figure Removed) wherein X is -NH- or - RIZ is -C3Hr-(n) or CH(C2H5)2, or X and R12 together are cyano, Rn is 2-NO2 or 3-Br, Ru 4-CF3l 4-CH3 or 4-OH, Ris 6-NO2 or 5-Br, and R-,6 is 3-CH3 or 5-NH2, are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, pages 1025, 779, 121 and 835; (Figure Removed) are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, pages 693,10, 21 and 220, and from AGROW No. 247, 5.1. (1996) page 19 and US-A-5 002 606; compounds of formula VIII (Figure Removed) X. is oxygen, NOC2H5 or NOCHrCH=CHCI (trans), are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, pages 909, 214 and 577; comoounds of formula IX wherein Xb is chlorine or CH3SO3| are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, page 767; the compound of formula X CH3-As(0)-(OH)2 (X), and its salts, especially the monosodium and disodium salts, are known, for example, from The Pesticide Manual, 10th ed. British Crop Protection Council 1994, page 683. Surprisingly, it has now been found that a combination of two active ingredients in variable proportions, i.e. a combination of the active ingredient of formula I with one of the above-mentioned active ingredients of formulae II to X, has a synergistic effect that is capable of controlling, both pre-emergence and post-emergence, the majority of weeds occurring especially in crops of useful plants without significantly damaging the useful plants. According to the present invention, therefore, a novel synergistic composition for selective weed control is proposed that comprises as active ingredient, in addition to conventional inert formulation adjuvants, the compound of formula I (Figure Removed) in admixture with a synergistically effective amount of at least one compound from the substance classes of formula II (Figure Removed) R is -Ci, -SCH3, -C4H9-(tert), methoxy, hydroxy, N(CH3)2| CHF2 or hydrogen; or U-V-W-Y together form the group -C(CF3)=C(R4)-C(CHrC3H7-Oso))=C(R5)-, wherein R* is (Figure Removed) wherein n is 0 or 1, R« is hydrogen, -CH3 or -NH2, R7 is hydroxy, C2H5, Na+, -CH(CH3)2-C02-CH=CH2 , -C4H9-n or -CHrCH2-O-N=C(CH3)2, and Q is the group (Figure Removed) wherein X is -NH- or - R12 is -C3H7-(n) or CH(C2H5)2, or X and R12 together are cyanc, R13 is 2-NO2 or 3-Br, Ru 4-CF3, 4-CH3 or 4-OH, R15 6-NO2 or 5-Br, and (Figure Removed) which corresponds to the salt of formula I is known, for example, from EP-A-0 103 453. By reaction with suitable salt-forming agents the compound of formula FI can be converted into the compound of formula I in a conventional manner known perse. Such salt-forming agents are, in principle, all bases that are capable of abstracting the acid hydrogen atom in the SO2-NH-CO- grouping. There have been found to be especially advantageous in this connection hydrides, hydroxides, alcoholates, hydrogen carbonates and carbonates of sodium. The reaction of the compound of formula FI with the bases to form the compound of formula I is carried out in a manner known per se, preferably in protic or aprotic solvents at room temperature or elevated temperature, in which reaction crown ethers and/or phase transfer catalysts may be present as is described, for example, in J. March, Advanced Org. Chem., John Wiley and Sons, 4th Edition, 1992: Phase Transfer Catalysis, page 362. For example, the compound of formula I can be obtained in good yields by simply stirring the compound of formula FI with aqueous sodium hydroxide solution at room temperature. Such methods are described, for example, in WO 97/41112. According to the invention, preference is given to compositions that comprise the compound of formula I and at least one compound selected from the compounds ametryn, atrazine, hexazinone, asulam, diuron, 2,4-D, halosulfuron and the compound of formula IV wherein Q is Qi, R7 is -C(CH3)2-C(O)O-CH2CH=CH2and n is 0. Of those compositions, special preference is given to those that comprise the compound of formula I and at least one compound selected from the compounds ametryn, atrazine, hexazinone and asulam. Prominence is to be given also to compositions that comprise the compound of formula I and at least one compound selected from the compounds fiuometuron, prometryn, metola-chlor, a-metolachlor, norflurazon, pyrithiobac-sodium, DSMA, MSMA, trifluralin, pendi-methalin, bromoxynil, glyphosate, glufosinate and clomazone. Of those, special mention is to be made of those compositions according to the invention that comprise the compound of formula I and at least one compound selected from the compounds fiuometuron, prometryn, metolachlor, a-metolachlor, norflurazon, pyrithiobac-sodium, MSMA and DSMA. When R6 in formula IV is other than hydrogen, the R-enantiomer of that formula is especially preferred. Compounds of formula II that are especially suitable for use in the composition according to the invention are those wherein a) A is Ai and E is Ei (common name: asulam) and b) A is A2 and E is E2 (common name: halosulfuron). Compounds of formula III that are especially suitable for use in the composition according to the invention are listed in Table 1: (Table Removed) The monosodium salt of the compound of formula X is known by the name MSMA. The disodium salt of the compound of formula X is known by the name DSMA. The compound of formula IX wherein X is chlorine is known by the name paraquat. It is extremely surprising that the combination of the active ingredient of formula I with an active ingredient of formula II, III, IV, V, VI, VII, VIII, IX or X surpasses the additive action on the weeds to be controlled that is to be expected in principle, and thus broadens the range of action of both active ingredients especially in two respects: Firstly, the rates of application of the individual compounds I and II, III, IV, V, VI, VII, VIII, IX and X are reduced while a good level of action is maintained. Secondly, the composition according to the invention achieves a high degree of weed control even in cases where the compounds individually, when used at low rates of application, have become no longer useful from an agronomic standpoint. The result of this is a considerable broadening of the weed spectrum and an additional increase in selectivity for crops of useful plants, as is necessary and desirable in case of inadvertent overdosage of the active ingredient. Furthermore, while maintaining outstanding control of weeds in useful plants, the composition according to the invention permits a greater flexibility with regard to subsequent crops. In addition, the onset of action of the compound of formula I can be accelerated in the presence of a mixing partner of formula II, lil, IV, V, VI, VII, VIII, IX or X. The herbicide mixture according to the invention can be used against a large number of agronomicaily important weeds, such as Stellaria, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solarium, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecu-rus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica. The compositions according to the invention are suitable for all the methods of application usual in agriculture, such as pre-emergence application, post-emergence application and seed dressing. The herbicide mixture according to the invention is suitable especially for weed control in crops of useful plants, such as cereals, rape, sugar beet, sugar cane, plantation crops (cotton), rice, maize and soybeans, more especially in crops of sugar cane and cotton (especially post-emergence application), and also for non-selective weed control. The compositions according to the invention are especially suitable for controlling the following weeds in crops of sugar cane: Erigeron canadensis, Convolvulus arvensis, Sorghum halepense, Imperata cylindrica, Cynodon dactylon, Commenlina benghalensis, Cyperus rotundus, Euphorbia heterophylla, Amaranthus retoflexus, Ipomoea hederacea, Brachiaria plantaginea, Digitaria sanguinalis, Eleusine indica, Panicum miliaceum and Setaria faberi. The compositions according to the invention are especially suitable for controlling the following weeds in crops of cotton: Cyperus rotundus, Sorghum bicolor, Digitaria sanguinalis, Echinochloa crus galli, Eleusine indica, Panicum dichotomiflorum, Setaria faberi, Brachiaria plantaginea, Abutilon, Amaranthus retoflexus, Cassia obtusifolia, Chenopodium album, Ipomoea hederacea, Sesbania exaltata and Xanthium canadense. Furthermore, compositions that comprise the compound of formula I and at least one herbicide selected from dithiopyr, prodiamine and simazine are especially suitable for use in lawns. The compound of formula I in combination with flazasulfuron (known from The Pesticide Manual, 9th ed., page 397) and isoxaflutole (known from BRIGHTON CROP PROTECTION CONFERENCE - Weeds -1995, Proceedings Volume 1, pages 35 - 42) also exhibits a synergistic herbicidal action, especially in sugar cane and lawns. Generally good action is also exhibited by a synergistic mixture consisting of the active ingredient of formula I and azafenidine (known from AGROW, No. 261, 2nd August 1996, page 23). Crops are also to be understood as including those which have been made tolerant towards herbicides or classes of herbicides by conventional breeding or genetic engineering techniques, for example maize, soybeans, cotton or sugar cane that is tolerant towards glyphos- ate, glufosinate, bromoxynil and ALS-inhibitors, such as surfonylureas (chlorimuron, thifen-sulfuron), imidazolinone (imazethapyr) or mixtures of those compounds. The active ingredient combination according to the invention comprises the active ingredient of formula I and the active ingredient of formula II, III, IV, V, VI, VII, VIII, IX or X in any desired mixing ratio, usually with an excess of the one component over the other. Preferred mixing ratios between the active ingredient of formula I and the mixing partners of formula II, III, IV, V, VI, VII, VIII, IX or X are from 1 :1 to 1: 350, especially from 1 : 5 to 1 : 70. The rate of application can vary within a wide range and depends on the nature of the soil, the type of application (ore- or post-emergence; seed dressing; application to the seed furrow; no tillage application), on the cultivated plant, the weed to be controlled, the prevailing climatic conditions and on other factors determined by the type of application, the time of application and the target crop. In general, the active ingredient mixture according to the invention may be used at a rate of application of from 0.008 to 5 kg/ha, especially from 0.3 to 2 kg/ha active ingredient mixture. The mixtures of the compound of formula I with the compounds of formula II, III, IV, V, VI, VII, VIII, IX orX can be used in unmodified form, i.e. as obtainable from synthesis, but are preferably formulated in customary manner with the adjuvants conventionally employed in formulation technology, such as solvents, solid carriers or surfactants, into e.g. directly sprayable or dilutable solutions, wettable powders, soluble powders, dusts, granules or microcapsuies. As with the nature of the compositions, the methods of application, such as spraying, atomising, dusting, wetting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The formulations, i.e. the compositions, preparations or mixtures comprising the compounds (active ingredients) of formulae I and II, III, IV, V, VI, VII, VIII, IX or X and, where appropriate, one or more solid or liquid formulation adjuvants, are prepared in a manner known per se, e.g. by homogeneously mixing and/or grinding the active ingredients with the formulation adjuvants, e.g. solvents or solid carriers. In addition, surface-active compounds (surfactants) can also be used in the preparation of the formulations. Suitable solvents are: aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms, such as xylene mixtures or substituted naphthalenes, phthalates, such as dibutyl or dioctyl phthalate, aliphatic hydrocarbons, such as cyclohexane, or paraffins, alcohols and giycols and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl or monoethyl ether, ketones, such as cyclohexanone, strongly polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or N,N-dimethytformamide, and also vegetable oils or epoxidised vegetable oils, such as epoxidised coconut oil or soybean oil, and water. The solid carriers used e.g. for dusts and dispersible powders are normally natural mineral fillers, such as calcite, talcum, kaolin, montmorillonite or attapulgite. In order to improve the physical properties of the formulation it is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers. Suitable granulated adsorptive carriers are porous types, for example pumice, broken brick, sepiolite or bentonite; and suitable non-sorbent carriers are, for example, calcite or sand. In addition, a great number of pregranulated materials of inorganic or organic nature can be used, such as, especially, dolomite or pulverised plant residues. Depending on the nature of the compound of formula I to be formulated, suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants and mixtures of surfactants having good emulsifying, dispersing and wetting properties. Both so-called water-soluble soaps and water-soluble synthetic surface-active compounds are suitable anionic surfactants. Suitable soaps are the alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts of higher fatty acids (C^-Caa), e.g. the sodium or potassium salts of oleic or stearic acid, or of naturally fatty acid mixtures which can be obtained e.g. from coconut oil or tallow oil. Mention may also be made of fatty acid methyltaurine salts. More frequently, however, so-called synthetic surfactants are used, especially fatty alcohol sulfonates, fatty alcohol sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates. The fatty alcohol sulfonates or sulfates are usually in the form of alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts and contain a Ce-Cazalkyl radical, which also includes the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of lignosulfonic acid, of dodecyl sulfate or a mixture of fatty alcohol sulfates obtained from natural fatty acids. These compounds also include the salts of sulfated and sulfonated fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and one fatty acid radical containing 8 to 22 carbon atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecyl-benzenesulfonic acid, dibutylnaphthalenesulfonic acid, or of a condensate of naphthalene-sulfonic acid and formaldehyde. Also suitable are corresponding phosphates, e.g. salts of the phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 mol of ethylene oxide, or phospholipids. Non-ionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols. Further suitable non-ionic surfactants are the water-soluble adducts of polyethylene oxide with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which adducts contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit. Examples of non-ionic surfactants are nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol. Fatty acids esters of polyoxyethylenesorbitan, e.g. polyoxyethylene sorbitan trioleate, are also suitable. Cationic surfactants are preferably quaternary ammonium salts which contain, as N-substituent, at least one Ce-C^lkyl radical and, as further substituents, unsubstituted or halogenated lower alkyl, benzyl or hydroxy-lower alkyl radicals. The salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, e.g. stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide. The surfactants customarily employed in formulation technology, which can also be used in the compositions according to the invention, are described inter alia in "Me Cutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp., Ridgewood New Jersey, 1981, Stache, H., "Tensid-Taschenbuch", Carl Manser Verlag, Munich/Vienna, 1981 and M. and J. Ash, "Encyclopedia of Surfactants", Vol l-lll, Chemical Publishing Co., New York, 1980-81. The herbicidal formulations usually contain 0.1 to 99 % by weight, especially 0.1 to 95 % by weight, of an active ingredient mixture of the compound of formula I with the compounds of formula II, III, IV, V, VI, VII, VIII, IX or X, 1 to 99.9 % by weight of a solid or liquid adjuvant, and 0 to 25 % by weight, especially 0.1 to 25 % by weight, of a surfactant. Whereas commercial products are preferably formulated as concentrates, the end user will normally employ dilute formulations. The compositions may also comprise further ingredients, such as stabilisers, for example vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rape oil or soybean oil), antrfoams, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers, as well as fertilisers or other active ingredients. Preferred formulations are composed in particular of the following constituents (throughout, percentages are by weight): Dusts: active ingredient mixture: solid carrier: Suspension concentrates: active ingredient mixture: water: surfactant: Wettable powders: active ingredient mixture: surfactant: solid carrier: Granules: active ingredient mixture: solid carrier: 0.1 to 10 %, preferably 0.1 to 5 % 99.9 to 90 %, preferably 99.9 to 99 % 5 to 75 %, preferably 10 to 50 % 94 to 24 %, preferably 88 to 30 % 1 to 40 %, preferably 2 to 30 % 0.5 to 90 %, preferably 1 to 80 % 0.5 to 20 %, preferably 1 to 15 % 5 to 95 %, preferably 15 to 90 % 0.1 to 30 %, preferably 0.1 to 15 % 99.5 to 70 %, preferably 97 to 85 % The following Examples illustrate the invention in more detail without limiting it. (Table Removed) It is often more practical to formulate the compound of formula I and the mixing partners of formula II, III, IV, V, VI, VII, VIII, IX or X individually and subsequently combine them in the desired mixing ratio as a tank mix in water shortly before application in an applicator. Biological Examples: A synergistic effect exists whenever the action of the active ingredient combination I and II, III, IV, V, VI, VII, VIII, IX or X is greater than the sum of the actions of the active ingredients applied individually. The herbicidal action to be expected, We, for a given combination of two herbicides can be calculated as follows (see COLBY, S.R. "Calculating synergistic and antagonistic response of herbicide combinations". Weeds 15, pages 20-22; 1967): We - X + [Y • (100 - X) /100] wherein: X = % herbicidal action in the case of treatment with the compound of formula I using an application rate of p kg per hectare, in comparison with untreated control (= 0%). Y = % herbicidal action in the case of treatment with a compound of formula II, III, IV, V, VI, VII, VIII, IX or X using an application rate of q kg per hectare, in comparison with untreated control. We = expected herbicidal action (% herbicidal action in comparison with untreated control) after treatment with the compounds of formula I and II, III, IV, V, VI, VII, VIII, IX or X at a rate of application of p + q kg of active ingredient per hectare. If the action actually observed is greater than the expected value We, then synergy exists. The synergistic effect of the combinations of the active ingredient of formula I with the active ingredients of formula II, III, IV, V, Vi, VII, VIII, IX or X is demonstrated in the following Example. Example B1: Pre-emergence herbicidal action: Monocotyledonous and dicotyledonous weeds and cultivated plants are sown in standard soil in plastics pots. Immediately after sowing, the test compounds are applied as an aqueous suspension (5001 of water/ha). The rates of application depend on the optimum concentrations determined under field conditions and greenhouse conditions. Evaluation of the tests is made after 15 and 27 days (OAA = day after application) in % action. 100 % denotes that the plants have died, 0 % denotes no phytotoxic action. The combinations of the active ingredient of formula I with the active ingredients of formula II, III, IV, V, VI, VII, VIII, IX or X exhibit a synergistic action in this test. Examples of the pre-emergence synergistic action of the compositions according to the invention are given in the following (Table Removed) In addition to the synergistic herbicidal action of the composition according to the invention on tne weeds, surprisingly an advantageous antagonistic action on the cultivated plant cotton was found, i.e. whereas the compound of formula I when applied at a rate of 3.75 g/ha damages cotton by 10 %, when 500 or 250 g/ha of norflurazon are added to the compound of formula I the cotton is protected to a very large extent (0 % damage) while the herbicidal action on the weeds is increased. Table B4: Pre-emergence herbicidal action of the composition according to the invention comprising the compound of formula I and oendimethalin on DAA 15: (Table Removed) Example B2: Post-emergence herbicidal action: The test plants are raised in plastics pots under greenhouse conditions as far as the 2- to 3-leaf stage. A standard soil is used as the cultivation substrate. At the 2- to 3-leaf stage, the herbicides are applied individually and as mixtures to the test plants. The test compounds are applied in the form of an aqueous suspension in 5001 of water/ha. The rates of application depend on the optimum concentrations determined under field conditions and greenhouse conditions. Evaluation of the tests is made after 11 and 22 days (DAA = day after application) in % action. 100 % denotes that the plants have died, 0 % denotes no phytotoxic action. The combinations of the active ingredient of formula I with the active ingredients of formula II, III, IV, V, VI, Vli, VIII, IX or X exhibit a synergistic action in this test. Examples of the post-emergence synergistic action of the compositions according to the invention are given in the following Tables. Table B6: Post-emergence herbicidal action of the composition according to the invention comprising the compound of formula I and fluometuron on DAA 11: (Table Removed) 1. A herbicidal synergistic composition which comprises, in addition to conventional inert formulation adjuvants, the compound of formula I (Figure Removed) in admixture with a synergistically effective amount of at least one compound from the substance classes of formula II wherein A is the group A-i H.N U-V is a group of the formula R^N, N=CR1( CONRi, RiNCO or wherein Ri is -NHC3Hr(iso), -NHC(CH3)2CN, -NHC4H9-(tert), - (Figure Removed) W-Y is a group of the formula CR2=N, CONR2) NRaCO, CONRs or wherein R2 is methyl, -Cl, -NH2l -NHCsHrflso) or -NHC2H5 and R3 is -NHCH3 or C4H9-(tert), and R is -Cl, -SCH3, -C4H9-(tert), methoxy, hydroxy, N(CH3)2) CHF2 or hydrogen; or U-V-W-Y together form the group -C(CF3)=C(R4)-C(CHrC3HrOso))=C(R5)-t wherein R4 is (Figure Removed) wherein n isOor 1, R6 is hydrogen, -CH3 or -NH2, R7 is hydroxy, C2H5, Na+, -CH(CH3)2-CO2-CH=CH2, -C4H9-n or -CH2-CHrO-N=C(CH3)2, and Q is the group (Figure Removed) 3-trifluoromethylphenyl or phenyl, R9 and Rio are each independently of the other hydrogen or methyl and (Figure Removed) wherein X is -NH- or - Ri2 is -C3H7-(n) cr CH(C2H5)2l or X and Ri2 together are cyano, R13 is 2-NO2 or 3-Br, Ru 4-CF3, 4-CH3 or 4-OH, Ris 6-NO2 or 5-Br, and R1S is 3-CH3 or 5-NH2; of formula VII Z-N(R17)-R16 (VII), wherein 2. (Figure Removed) 3. A herbicidal composition according to WE CLAIM: 1. A herbicidal synergistic composition which comprises, in addition to conventional inert formulation adjuvants of the kind such as herein described, trifloxysulfuron sodium in admixture with a synergistically effective amount of a compound from the substance class of formula IV (Formula Removed) wherein n is 0 or 1, R6 is hydrogen, -CH3 or -NH2, R7 is hydroxy, C2H5, Na+, -CH(CH3)2-CO2 -CH=CH2 -C4H9-n or -CH2-CH2-O-N=C(CH3)2 and Q is the group (Formula Removed) and salts thereof; wherein trifloxysulfuron sodium is present in a weight ratio of from 1:1 to 1:350 in relation to the component of formula IV. 2. A herbicidal composition as claimed in claim 1, which comprises trifloxysulfuron sodium and at least one compound selected from the compounds 2-4-D, pyrithiobac- sodium, glyphosate, glufosinate, quizalofop, fenoxaprop-P, lactofen, fluazifop, propaquizafop and dicamba. 3. A herbicidal synergistic composition substantially as herein described with reference to the foregoing examples.

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0202-del-1998-abstract.pdf

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