IE19980064A1 - Synergistic herbicidal agents - Google Patents

Description

SYNERGISTIC HERBICIDAL COMPOSITIONS This invention relates to herbicidal compositions comprising A) a compound of the formula I or salts thereof in combination with B) one or more compounds selected from the group comprising growth-regulator-type herbicides, dicamba and salts thereof, diflufenican, nitrodiphenyl ethers, sulfonylureas which differ from the urea of the formula (I), and salts thereof, and selective grass herbicides.

These compositions are particularly useful in the selective control of weeds in rice, soya and other crops.

'.Description Synergistic herbicidal compositions The invention is in the field of the crop protection agents which can be employed against monocotyledon and dicotyledon weeds, in particular in the combination of herbicides.

The action of an individual herbicide used in acceptable application rates is frequently insufficient for con- trolling the spectrum of monocotyledon and dicotyledon weeds which exists in agricultural practise. To allow the grower to control the weed spectrum in cereals, maize and other crops with one or a few application(s) of her- bicidal active substances, it is sometimes more suitable to use combinations of a variety of active substances.

Combinations of herbicides have now been found whose action, surprisingly, exceeds the extent which would have been expected taking into account the individual action of the The according to the invention, therefore allow a surprising- ly great reduction in application rate of each of the components. combinations of herbicides, components.

The invention therefore relates to herbicidal com- positions which comprise A) a compound of the formula I or salts thereof 3} T0 Pueuc mspecrgou’ . X in combination with B) one or more compounds selected from the group comprising growth-regulator-type herbicides, dicamba and salts thereof, diflufenican, nitrodiphenyl ethers, sulfonylureas which differ from the urea of the formula (I), grass herbicides. and salts thereof, and selective The compound of the formula (I) is known as amidosulfuron and disclosed in EP-A-0,131,258 (US-A-4,718,937).

Amidosulfuron is a herbicidal active substance from the group comprising the sulfonylureas and is generally and post-emergence in cereals, rice and 120 g of controlling a broad spectrum of annual and perennial applied pre- maize at application rates of 5 - broad-leaf weeds and Cyperaceae (g of a.i./ha = gram per hectare based on active ingredient). For use, the active substance is generally formulated as a WP (water-soluble powder) or WDG (water-dispersible granules) and employed in the customary manner in the form of a dilution with water.

Particularly suitable growth-regulator-type herbicides are the following: i.e. a) MCPB 4-(4-chloromethylphenoxy)- butanoic acid or salts thereof (for example the sodium salt); b) mecoprop i.e. 2-(4-chloromethylphenoxy)- propionic acid or salts thereof; in the form of a racemic mixture or as the (R)- isomer (mecoprop-P); c) 2,4-D i.e. 2-(2,4-dichlorophenoxy)acetic acid or salts thereof or esters thereof; d) 2,4-DB i.e. acid or salts thereof; 4-(2,4-dichlorophenoxy)butanoic IE 980064 e) dichlorprop i.e. 2-(2,4-dichlorophenoxy)propionic acid or salts thereof or esters thereof, f) MCPA i.e. 2-(4-chloromethylphenoxy)acetic acid or salts thereof.

The abovementioned compounds a) to f) represent standard herbicides which are used post-emergence in a large number of agriculturally used crops for controlling needs and Cyperaceae. Application rates of 100 - 3000 g of a.i./ha as individual active substances cover in each case a specific sector of the weed flora. The various compounds are used in the forms of the salts "The Pesticide Manual", 9th Edition 1991 and and/or esters (references: cf.

British Crop Protection Council, references cited therein).

Dicamba, i.e. 3,6-dichloromethoxybenzoic acid (or the salts thereof and esters thereof), is also a widely used herbicidal active substance which is applied analogously to the growth-regulator herbicides. The active substance is mainly used post-emergence (for example, inter alia, in cereals and maize), likewise in the forms of the salts thereof (cf. "The Manual", already mentioned above). and/or esters thereof Pesticide Diflufenican, i.e. N—(2,4-difluorophenyl)[3-(tri- fluoromethyl)phenoxy]pyridinecarboxamide, is employed pre— and post-emergence for controlling weeds in cereals and other crops at a rate of 50 - 500 g of a.i./ha. It is marketed. mostly in the fornl of finished formulations together with other herbicidal active substances (of.

"The Pesticide Manual", already mentioned above).

Particularly suitable nitrodiphenyl ethers are the following: a) bifenox, i.e. methyl 5-(2,4-dichlorophenoxy)- 1000 g of a.i./ha when used as single active substance pre- 2-nitrobenzoate; application rate 50 — IE 980064 and post-emergence, for example in cereals, rice and maize. fluorglycofen, i.e. carboxymethyl 5-[2-chloro- 4-(trifluoromethyl)phenoxy]nitrobenzoate; application as single active substance for example only 5 — 50 g of a.i./ha pre- and post-emergence in cereals and soya. i.e. acifluorfen, 5-[2-chloro(trifluoromethyl)- phenoxy]nitrobenzoic acid or salts thereof; application as single active substance for example at a rate of 100 - 500 g of a.i./ha pre- and post- emergence in soya and cereals. -[2-chloro(trifluoromethyl)- oxyfluorfen, i.e. phenoxy]ethoxynitrobenzene; application as single active substance for example at a rate of 100 - 1000 g of a.i./ha pre- and post-emergence in soya or on areas not under cultivation. lactofen, i.e. 1-(ethoxycarbonyl)ethyl 5-[2-chloro- 4-(trifluoromethyl)phenoxy]nitrobenzoate; application as single active substance for example at a rate of 50 — 500 g of a.i./ha pre- and post- emergence in soya and cereals. fomesafen, i.e. N—methylsu1fonyl[2-chloro~4- (trifluoromethyl)phenoxy]nitrobenzamide; application as single active substance for example at a rate of 50 - 1000 g of a.i./ha pre- and post- emergence in soya or cereals.

All of the nitrophenyl ethers mentioned are described in "The Pesticide Manual“ (already mentioned above).

Particularly suitable sulfonylureas are the following: IE 980064 _ 5 _ sulfonylureas which are employed mainly in cereals, in some cases in potatoes and in grassland for post- emergence control of broad-leaf and grass weeds (for example at a rate of 5 - 80 g of a.i./ha), for example aa) triasulfuron, i.e. 1-[2-(2-ch1oroethoxy)- phenylsulfonyl](4-methoxymethyl- 1,3,5-triazinyl)-urea; ab) chlorsu1furon,i.e.1-(2-chlorophenylsulfonyl)- 3-(4-methoxy-6¥methyl-1,3,5—triazinyl)-urea; 1—[2- (carboxy— or methoxycarbonyl)pheny1su1fonyl]- ac) tribenuron or tribenuron—methy1, i.e. 3-methyl(4-methoxy-6—methyl-1,3,5-triazin- 2-yl)-urea; ad) thifensulfuron or thifensulfuron-methyl, i.e. 1-[2-(carboxy— or methoxycarbonyl)-thiophen-3~ yl-sulfony1](4-methoxymethyl-l,3,5- triazinyl)-urea and sulfonylureas which are employed mainly in maize and perennial crops for post-emergence control of grass and broad—leaf weeds (5 - 80 g of a.i./ha), for example be) nicosulfuron, i.e. 1-[3-(dimethylamino- carbonyl)-pyridinyl-sulfonyl](4,6- dimethoxypyrimidinyl)—urea; bb) primisulfuron or primisulfuron-methyl, i.e. 1-[2-(carboxy- or methylcarbonyl)-phenyl- sulfonyl]—3-[4,6—bis(dif1uoromethoxy)- pyrimidinyl]-urea; bc) DPX-E 9636, i.e. 1-[3-(ethylsulfonyl)-pyridin- 2-yl-sulfonyl](4,6-dimethoxypyrimidyl)- urea; bd) pyridylsulfonylureas as they are described in PCT Patent PCT/EP 90/02308 (WO 91/10660), those of the formula A1 or salts thereof Application preferably IE 980064 O~‘ R’ __: Pl 0 3'‘ N=-< R ’*5;'-hH‘LLF—<\ 2 (A1) 0 R_( in which E is CH or N, preferably CH, R‘ is iodine or NR°R1°, R5 is H, halogen, cyano, C,-C3-alkyl, C1-C3—alkoxy, C1-C3-haloalkyl, C1-C3—ha1oa1koxy, C1-C3-alkylthio, (C1-C3-alkoxy ) -C1-C3-alkyl , (C1-C3-alkoxy) -carbonyl, mono- or di-(C1-C3- alkyl ) -amino, C1-C3-alkyl-sulfinyl or -sulfonyl, S02-NR‘R" or C0-NR'Rb, in particular 3, R“ and R”, independently of one another are H, C1-C3-alkyl, C1-C3-alkenyl, C1-C3-alkynyl, or together are -(CI-12).: , - ( CH2 ) 5- or ’(CH2)2'O"(CH2)2‘r is H or CH3, is halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2- haloalkyl, preferably CF3, C1-C2-haloalkoxy, preferably OCHFZ or OCHZCF3, is C1-C2-alkyl, C1-C2-haloalkoxy, preferably OCHF2 or C1-C2-alkoxy, and is C1-C,-alkyl and R1° is C1-C,-alkylsulfonyl, or R9 and R" together are a chain of the formula -(CH2)3SO2- or -(CH2),,SO2-.

IE 980064 The herbicides mentioned above under aa) to ba) are described in "The Pesticide Manual" (already mentioned above).

Primisulfuron and primisulfuron-methyl are-known from Brighton Crop Protection Conference - Weeds - 1987, p. 41 - 48.

DPX-E 9636 is known from Brighton Crop Protection Conference — Weeds — 1989, p. 33 et seq..

Suitable herbicides are mainly the following herbicides for the selective post-emergence control of grass harmful plants (grass weeds and broad-leaf weeds) in cereals (range of application rates 30 to 1000 g of a.i./ha): i.e. 2-[4—(2,4— dichlorophenoxy)phenoxy]propionic acid or its methyl a) diclofop or diclofop-methyl, ester; b) tralkoxydim, i.e. 2-[1-(ethoxyimino)—propyl] hydroxymesitylcyclohexenone; c) difenzoquat, i.e. 1,2-dimethy1-3,5-diphenyl- pyrazolium salts; d) imazamethabenz, i.e. a mixture of 6-(4-isopropyl methyl—5—oxo—2—imidazolinyl)methyl-benzoic acid and —4—methyl-benzoic acid or their methyl esters; e) flamprop or flamprop-methyl, i.e. N-benzoyl—N-(3- chlorofluorophenyl)-alanine, or its methyl ester; f) CGA-184927, i.e. propargyl (2R)[4-(5-chloro fluoropyridinyloxy)-phenoxy]—propionate.

The last-mentioned compounds a) to e) are likewise des- cribed in "The Pesticide Manual" (see above).

CGA-184927 is known from EP-A-191,736 and Brighton Crop Protection Conference - Weeds - 1989.

IE 980064 that (= synergistic) effects occurred when amidosulfuron was Surprisingly, it has emerged superadditive used together with one or more active substances from group B. The action in the combinations was greater than that of the single products used on their own. effects allow the application rate to be reduced, a broad These spectrum of broad-leaf weeds and grass weeds to be controlled, a more rapid action, a prolonged long-term action, a complete control of the harmful plants with only one, or few, applications, and a widening of the potential application period when the active compounds are combined. These properties are required for practical weed control to keep agricultural crops free from un- desired competitive plants and thus to guarantee the quality and quantity of the yields and/or to increase them. These novel combinations markedly outperform the state of the art with regard to the properties described.

The choice of the ratio by weight and the application rates are a function of, for example, the other component in the mixture, the development stage of the broad-leaf environmental weeds or grass weeds, the weed spectrum, factors and climatic conditions.

The ratios by weight A:E of the combined herbicides can therefore vary within wide limits and are generally 1:200 to 20:1.

The following ratios by weight are preferably used: In the case of combinations of the compounds of the formula (I) or salts thereof - with growth-regulator herbicides: 1:200 to 2:1, preferably 1:50 to 1:1; - with dicamba: 1:200 to 2:1, preferably 1:50 to 1:1; IE 980064 _ 9 _ - with diflufenican: 1:200 to 5:1, preferably 1:50 to 2:1; — with nitrodiphenyl ethers: 1:200 to 10:1, preferably 1:50 to 5:1; - with sulfonylureas: 1:16 to 20:1, preferably 1:10 to 20:1; - with grass herbicides: 1:200 to 3:1, preferably 1:50 to 10:1.

The application rates of the herbicide A in the active substance combinations are preferably between 5 and 100 g of a.i./ha (a.i. = relative to active ingredient). The application rates of B type compounds in the mixtures are generally from 5 to 100 g of a.i./ha, preferably — with growth-regulator herbicides 50 to 1000 g of a.i./ha, - with dicamba 50 to 1000 g of a.i./ha, — with diflufenican 20 to 1000 g of a.i./ha, - with nitrodiphenyl ethers 10 to 1000 g of a.i./ha, with sulfonylureas 5 to 80 g of a.i./ha, with grass herbicides 30 to 1000 g of a.i./ha.

The active substance combinations according to the invention can exist as ndxed formulations of the two components which are then applied in the customary manner in the form of a dilution with water, or are prepared in the form of so—called tank mixes by concomitant dilution of the separately formulated components with water.

The A type and B type compounds or their combinations can be formulated in many ways, depending on the prevailing biological and/or chemicophysical parameters. The follow- ing are possible exemplary formulations: wettable powders (WP)r (SL)r emulsifiable concentrates (EC), aqueous solutions emulsions (EW) such as oil-in-water and IE 980064 _ 10 _ water-in-oil emulsions, sprayable solutions or emulsions, dispersions on an oil or water basis, suspoemulsions, dusting powders (DP), seed-dressing agents, granules for soil application or for broadcasting, or water- dispersible granules (WG), ULV formulations, micro- capsules or waxes.

The individual formulation types are known in principle and are described, for example, in: Winnacker-Kfichler, "Chemische Technologie [Chemical Technology]", Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986; van Valkenburg, "Pesticides Formulations", Marcel Dekker N.Y., 1973; K. Martens, "Spray Drying Handbook", 3rd Ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries required such as inert materials, surfactants, solvents and other additives are equally known and are described, for example, in: Watkins, Carriers", "Handbook of Insecticide Dust Diluents and 2nd Ed., Caldwell N.J.; H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y. Marsden, "Solvents Guide", Darland Books, 2nd Ed., Interscience, N.Y. 1950; McCutcheon’s, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridegewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schdnfeldt, "Grenzflachenaktive Kthylenoxidaddukte [Surface—active Ethylene Oxide Adducts]", Wiss. Verlags- gesellschaft, Stuttgart 1976, Winnacker-Kfichler, "Chemische Technologie [Chemical Technology]", Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986.

Based on these formulations, it is also possible to prepare combinations with other pesticidally active substances such as other herbicides, fungicides or insecticides, as well as safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or a tank mix.

IE 980064 Wettable powders are preparations which can be dispersed uniformly in water and which comprise, beside the active substance, ionic or non-ionic surfactants (wetting agents, dispersants), for example polyoxethylated a1kyl— phenols, polyethoxylated fatty alcohols or fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates or alkylbenzenesulfonates, sodiuntligninsulfonate, sodium 2,2'-dinaphthylmethane—6,6'—disulfonate, sodium dibutyl- oleoylmethyl— taurinate, besides a diluent or inert substance. naphthalenesulfonate or else sodium Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else higher-boiling aromatics or hydrocarbons, with the addition of one or more ionic or non-ionic surfactants (emulsifiers). The following are examples of emulsifiers which can be used: calcium alkylarylsulfonates such as calcium:dodecylbenzenesulfonate, or non-ionic emulsifiers alkylaryl poly- glycol ethers, fatty alcohol polyglycol ethers, propylene such as fatty acid polyglycol esters, oxide/ethylene oxide condensation products, alkyl poly- ethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxethylene sorbitol esters.

Dusting powders are obtained by grinding" the active substance with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Granules can be prepared either by spraying the active substance onto adsorptive, granulated inert material or by applying active substance concentrates to the surface of carrier substances such as sand, kaolinites or granu- lated inert material with the aid of adhesives, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active substances can also be IE 980064 _ 12 - granulated in the fashion customary for the preparation of fertilizer granules, if desired in the form of a mixture with fertilizers. Water-dispersible granules are spray-drying, fluidized-bed granulation, disk granulation, mixing with generally prepared by methods such as high~speed mixers and extrusion without solid inert material.

As a rule, the agrochemical preparations comprise 0.1 to 99 % by weight, in particular 2 to 95 % by weight, of active substances of types A + B. The concentrations of differ in the the active substances A + B can formulations.

For example, the active substance concentration in wettable powders is approximately 10 to 95 % by weight, the remainder to 100 % by weight is composed of customary formulation components. In the case of emulsifiable concentrates, the active substance concentration can be approximately 1 to 85 % by weight, preferably 5 to 80 % by weight. Formulations in the form of dusts comprise approximately 1 to 25 % by weight, usually 5 to 20 % by weight, of active substance, sprayable solutions ap- proximately 0.2 to 25 % by weight, preferably 2 to 20 % by weight, of active substance. In the case of granules such as dispersible granules, the active substance content depends partly on whether the active compound is liquid or solid and on which granulation auxiliaries and fillers are used. The content in the case of the water- dispersible granules is generally between 10 and 90 % by weight.

Besides, the active substance formulations mentioned optionally comprise the adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, colorants and carriers, defoamers, evaporation inhibitors, pH regu- lators and viscosity regulators which are customary in IE 980064 -13.. each case.

For use, the formulations which exist in commercially available form are optionally diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in the form of dusts, granules for soil application or for broadcasting solutions are customarily not as well as diluted further with other application. sprayable inert substances before The active substances can be applied to the plants, parts of the plants, cultivation.

The active substances are preferably applied jointly in seeds of the plants or the area under the form of tank mixes, the optimally formulated con- centrated formulations of the single active substances being mixed concomitantly with water in the tank, and the spray mixture obtained is applied.

The examples which follow are intended to illustrate the invention: A. Formulation examples a) A dusting agent is obtained by mixing 10 parts by weight of an active substance combination according to the invention and 90 parts by weight of talc as inert substance and comminuting the mixture in a hammer mill. b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active substances A + B, 64 parts by weight of kaolinvcontaining quartz as inert substance, parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurate as wetting and dispersing agent, and grinding the mixture in a pinned disk mill.

K)‘.

IE 980064 _ 14 - A dispersion concentrate which is readily disper- sible in water is obtained by mixing 20 parts by weight of active substances A + B with 6 parts by weight of alkylphenol polyglycol ether (“Triton X 207), 3 parts by weight of isotridecanol poly- glycol ether (8 E0) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, approx. 255 to 277°C), and grinding the mixture in a ball mill to a fineness of below 5 microns.

An emulsifiable concentrate is obtained from parts by weight of cyclohexanone as solvent and parts by weight of oxethylated nonylphenol as emulsifier.

Water-dispersible granules are obtained by mixing 75 parts by weight of active substances A + B, parts by weight of calcium ligninsulfonate, parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin, grinding the mixture on a pinned. disk. mill and granulating the powder in a fluidized bed by spray- ing on water as granulation liquid.

Alternatively, water-dispersible granules are obtained by homogenizing and precomminuting parts by weight of active substances A + B, parts by weight of sodium 2,2’-dinaphthy1methane— 6,6’-disulfonate, 2 parts by weight of sodium oleoylmethyltaurate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water on a colloid mill, subsequently grinding the mixture on a bead mill, and atomizing and drying the result- ing suspension in a spray tower by means of a single-substance nozzle.

IE 980064 B. Biological examples Various economically important broad-leaf weeds and grass weeds had grown under natural field conditions (field trials). The herbicide mixtures were applied in the 2- to -leaf stage of the crop plants and the harmful plants by means of plot spray equipment. The water application rate was 300 - 400 liters of water per hectare.

Within 4 weeks after the application, the herbicidal activity of the treated plots was assessed by comparison with untreated control plots by visual scoring. The herbicidal action as regards influencing the plant growth and chlorotic and necrotic effects up to the total destruction of the weeds was assessed qualitatively and indicated as action quantitatively and percentage (0 - 100 2;).

The results are compiled in Tables 1 and 2 below: IE 980064 aounmanmovwfim “ AH. vnaomaou Ahwahmn mswummu wnmmazb Edovuom u m>mom Eflfldd Enwvomoamao u Adamo mwamuumsm xwfim u Dmmzm maavnoamu mumnuouuum n «comm o mm mm ma o~« + on _ o an up an com + on _ m + d o cm on on can _ o o_ m_ ow omv % c M on on cow «mu: m o mm am w ow o mm pm m mv o no mm ¢ cm ..H. caaomeou < wmmfidv w HOH#fiOU w m>mom gamma pmmzm ¢oom¢ m:\.w.m no a .m.oo:uumn:m m>«uo< H manna IE 980064 SOH§HH§mOUHEd u AH. Uzsomfioo mummasb Edwuuom u m>mom E3£HM Enwuomocmno " Amman w:H=>Ho>:oo Encomaaom u ounom mama: muwmmmum u dzmmm m5NOHHOHHOH mfinunmnmfifl H Mmdzfl o ooa mm oofi mm omm + on o oofi mm oofl mm cad + om mm + m o ooa wm co“ mm omq + on e on mm mm om cam + on mm + fl o om ma on me omm o «H ofi ma om ofifl mnsmofiu u Nm c on on em me ovm c an we mm um owe a ma «H mm on can a-¢.~ u an o mm mm ma mm ow o mm an mm mp me o no as he on cm .H. ucsomaoo n < ommfidv w Hohunou m m>mom émwmo ooqom «gm 5% 9: . ._. .m we m Tm V oocaumnsm w>Uo¢ N magma IE 980064 The examples in the Tables show that only high dosage rates of the single active substances allow good control of individual weeds. The components in the ndxtures, applied at low dosage rates, only show poor activity, far less than required in practise. The concomitant use of the active substances allow good effects to be achieved on all test weed species. The additive action of the individual components was markedly exceeded (synergism), i.e. the control level required is achieved by markedly These effects broaden the lower application rates. spectrum of action.

The crop tolerance, assessed in the form of damage, is not adversely affected, i.e. the combinations can be judged as fully selective.

IE 980064 Patent claims: 1. A herbicidal composition which comprises A) a compound of the formula I or salts thereof 3', j..;/L“ ‘H 1-23c-so: \N so NH co H /,- \ ‘ti _4‘\ / 2 \_ /’ 1-13c ‘ \ in combination with B) one or more compounds selected from the group comprising growth-regulator~type herbicides, dicamba and salts thereof, diflufenican, nitrodiphenyl ethers, sulfonylureas which differ from the urea of the formula (I), and salts thereof, and selective grass herbicides. 2. A composition as claimed in claim 1, wherein the B type herbicides consist of grouth—regu1ator herbi- cides selected from amongst the group comprising MCPB, mecoprop, 2,4-D, 2,4-DB, dichlorprop and.MCPA, nitrodiphenyl diflufenican, as well as dicamba, ethers selected from group acifluorfen, oxyfluorfen, lactofen and fomesafen, as well as sulfonylureas selected from the comprising triasulfuron, chlorsulfuron, tribenuron, tribenuron-methyl, thifensulfuron, thifensulfuron- methyl, nicosulfuron, Primisulfuron, primisu1— comprising group ",'1 IE 980064 furon-methyl, DPX-E 9639 and pyridylsulfonylureas, as well as grass herbicides selected from the group comprising diclofop, diclofop-methyl, tralkoxydim, flamprop, flamprop- difenzoquat, imazamethabenz, methyl and CGA-184927.

A composition as claimed in claim 1 or 2, which comprises the compound (I) or salts thereof and the compounds selected from group B in a ratio by weight of 1:200 to 20:1.

A composition as claimed in one of claims 1 to 3, which comprises, besides the active substances of type A or B, customary formulation auxiliaries.

A process for the preparation of a composition as claimed in one or more of claims 1 to 4, which comprises formulating the compound of the formula (I) or salts thereof with one or more B type compounds analogously to a customary crop protection agent formulation selected from the group comprising wettable powders, emulsifiable concentrates, aqueous (tank mix), dispersions on an oil or water basis, suspo- solutions, emulsions, sprayable solutions emulsions, dusting powders, seed-dressing agents, granules for soil application or for broadcasting, formulations, water—dispersible granules, ULV microcapsules and waxes. which comprises applying a herbicidally effective amount A. method of controlling undesired plants, of a combination of active substances A. + B as defined in one or more of claims 1 to 4, to these plants or to the area under cultivation.

The method as claimed in claim 6, wherein the rates of the formula (I) or salts thereof are from 5 to 100 g/ha application compounds of the IE 980064 and the application rates of the B type compounds are from 5 to 1000 g/ha. 8. The method as claimed in claim 6 or 7, wherein the active substances of types A and B are applied in a ratio by weight of 1:200 to 20:1. 9. The use of a composition as defined in one or more of claims 1 to 4 for controlling undesired plant growth. wherein harmful plants in crops of useful plants are controlled . The use as claimed in claim 9, selectively.

A herbicidal composition according to claim 1, substantially as hereinbefore described and exemplified.

A process for the preparation of a composition according to claim 1, substantially as hereinbefore described and ex- emplified.

A composition according to claim 1, whenever prepared by a process claimed in claim 5 or 12.

A method according to claim 6, substantially as hereinbefore described and exemplified.

Use according to claim 9, substantially as hereinbefore described.

F. R. KELLY & CO., AGENTS FOR THE APPLICANTS.