NZ755110B2 - Ternary herbicide combinations - Google Patents

Abstract

Herbicide combinations comprising an effective amount of components (A), (B) and (C) wherein (A) denotes one or more herbicides selected from the group of compounds of the formula (I) and salts thereof, (B) denotes one or more herbicides selected from the group of the compounds of the formula (II) and their salts, (C) denotes at least one compound selected from the group consisting of (C-1) thienecarbazone-methyl; (C-2) pyroxsulam; (C-3) halauxifen; (C-4) pinoxaden; (C-5) pyroxasulfone; and/or salts thereof nd their salts, (C) denotes at least one compound selected from the group consisting of (C-1) thienecarbazone-methyl; (C-2) pyroxsulam; (C-3) halauxifen; (C-4) pinoxaden; (C-5) pyroxasulfone; and/or salts thereof

Description

TERNARY HERBICIDE COMBINATIONS ption The invention is in the technical field of crop protection products which can be employed against harmful plants, for e in crop plants, and which comprise, as active compounds, a combination of at least three herbicides.

The documents WO 92/13845 and WO 07 disclose ylureas and their salts and also their use as herbicides and/or plant growth regulators.

WO 03/073854 discloses ternary combinations containing the sulfonylurea herbicides iodosulfuron and lfuron and further herbicides, such as bazone.

A2 discloses synergistic herbicidal mixtures comprising A) pyroxsulam or its salts, B) at least one herbicidal compound selected from a long list of further herbicides, and, if desired, C) at least one safener.

US 6,221,809 B1 discloses binary combinations comprising (i) lfuron or a salt thereof, and (ii) a further herbicide, among which lfuron is mentioned.

US 6,492,301 B1 and US 6,864,217 B1disclose herbicidal compositions containing (i) at least one herbicidally active compound from the group of certain substituted phenylsulfonylureas and their agriculturally acceptable salts, and (ii) at least one compound from the group of herbicides which are selective in rice.

A2 ses combinations containing (i) a pyridine or pyrimidine carboxylic acid component, such as for example halauxifen, and (ii) a second cereal or rice herbicde component, wherein inter alia sulfonylurea herbicides such as iodosulfuron and mesosulfuron are mentioned.

A1 discloses idal itions comprising a mixture of (a) a first herbicide of a certain type and (b) pinoxaden.

Substituted thienylsulfonylamino(thio)carbonyltriazolin(ethi)ones are known to be effective herbicides (cf.

WO 01/05788).

The efficacy of these herbicides against harmful plants in the crop plants is at a high level, but depends in general on the application rate, the formulation in question, the harmful plants or spectrum of harmful plants to be controled in each case, the ic conditions, the soil conditions and the like. Another criterion is the duration of action, or the own rate of the ide. If appropriate, changes in the sensitivity of harmful plants, which may occur upon prolonged use of the herbicides or within geographic limitations must also be taken into consideration. The compensation of losses in action in the case of individual harmful plants by increasing the application rates of the herbicides is only possible to a certain degree, for example because such a ure frequently reduces the selectivity of the herbicides or e the action is not improved, even when applying higher rates. In some cases, the selectivity in crops can be improved by adding safeners.

In general, however, there remains a need for methods to achieve the herbicidal action with a lower ation rate of active compounds. Not only does a lower application rate reduce the amount of an active compound required for application, but, as a rule, it also reduces the amount of formulation auxiliaries required. It both reduces the economic input and improves the ecological compatibility of the herbicide treatment.

One possibility of improving the application profile of a herbicide can consist in combining the active compound with one or more other active nds. However, the combined use of a plurality of active compounds frequently causes phenomena of physical and biological atibility, for example a lack of stability in a coformulation, decomposition of an active compound, or antagonism of the active compounds.

What is d are, in contrast, combinations of active compounds having an advantageous ty profile, high ity and, if possible, a istically improved action, which allows the application rate to be reduced in ison with the individual application of the active compounds to be combined.

Surprisingly, it has now been found that • certain active compounds from the group of sulfonylureas or their salts in combination with • certain herbicides, preferably ALS inhibiting herbicides from the group of the sulfonylaminocarbonyltriazolinones , in particular, thiencarbazone (C) act together in a particularly ageous manner, for example when they are employed in crop plants which are suitable for the selective use of the ides, if appropriate with addition of safeners.

The invention therefore provides herbicide combinations comprising an effective amount of components (A), (B) and (C), wherein (A) denotes one or more herbicides selected from the group of the compounds of the formula (I) and their salts R O O O O N N N N O H H H (I), wherein R is hydrogen or a C1-C5-alkyl group, preferably R is methyl; (B) denotes one or more herbicides selected from the group of the compounds of the a (II) and their salts R O O O O N N N N N O H H I (II), wherein R is en or a C1-C5-alkyl group, preferably R is methyl; (C) denotes at least one compound selected from the group consisting of (C-1) thienecarbazone-methyl; (C-2) pyroxsulam; (C-3) halauxifen; (C-4) pinoxaden; (C-5) pyroxasulfone; and/or salts or esters thereof.

If, in the context of this description, the short form of the common name of an active compound is used, this includes in each case all customary derivatives, such as the esters and salts, and isomers, in particular optical isomers, in particular the commercially ble form or forms. If the common name denotes an ester or salt, this in each case also comprises all other customary derivatives, such as other esters and salts, the free acids and neutral compounds, and isomers, in particular optical isomers, in particular the cially ble form or forms. The given chemical compound names denote at least one of the compounds embraced by the common name, frequently a red compound. In the case of sulfonamides such as sulfonylureas, salts also include the salts formed by exchanging a hydrogen atom on the sulfonamide group by a cation.

The ide (C) is suitable for controlling monocotyledonous and dicotyledonous harmful .

The salts of compounds of the formulae (I) and (II) in the t of the present invention preferably are in the form of the respective alkali metal salts, alkaline earth salts or ammonium salts, preferably in the form of the respective alkali metal salts, more preferably in the form of the tive sodium or potassium salts, most preferably in the form of the respective sodium salts.

The salts of compounds (C) in the context of the present invention preferably are in the form of the respective alkali metal salts, alkaline earth salts or ammonium salts, preferably in the form of the respective alkali metal salts, more preferably in the form of the respective sodium or potassium salts, most preferably in the form of the respective sodium salts.

The herbicide combinations according to the invention comprise a herbicidally effective amount of components (A), (B) and (C) and may se further components, for example agrochemically active compounds of a ent type and/or formulation auxiliaires and/or additives customary in crop protection, or they may be employed together with these. Preference is given to herbicide combinations comprising a synergistically effective amount of components (A), (B) and (C).

In a preferred embodiment, the herbicide combinations according to the invention have synergistic effects.

The synergistic effects are observed, for example, when the active compounds (A), (B) and (C) are d together, but they can frequently also be observed when the compounds are applied as a split application over time. Another possibility is the application of the individual herbicides or the herbicide combinations in a plurality of portions (sequential application), for example after ergence ations, ed by postemergence applications or after early post-emergence applications, followed by applications at medium or late post-emergence. red is the simultaneous or nearly simultaneous application of the active compounds of the herbicide combination according to the invention. In a preferred embodiment, the herbicide combinations according to the invention are mixtures or compositions comprising the active compounds (A), (B) and (C) together.

[Link] http://www.alanwood.net/pesticides/derivatives/halauxifen-methyl.html [Link] http://www.alanwood.net/pesticides/derivatives/halauxifen-methyl.html The istic effects allow the application rates of the individual active nds to be reduced, a more potent action at the same application rate, the control of hitherto rolable species (activity gaps), an extended application period and/or a reduced number of individual applications required and - as a result for the user - more advantageous weed control systems both from an economical and ecological point of view.

The above mentioned formulae (I) and (II) include all stereoisomers and their mixtures, in ular also racemic mixtures and - if omers are possible - the respective biologically active enantiomer. nds of the formulae (I) and (II) and their salts and also their preparation are described, for example, in WO 92/13845 and WO 95/10507. Preferred compounds of the formulae (I) and their salts are methyl 2-[3- imethoxypyrimidinyl)ureidosulfonyl]methanesulfone-aminomethyl-benzoate (mesosulfuron- methyl, A1-1) and its salts, such as the sodium salt (mesosulfuron-methyl-sodium, A1-2) (see, for example, WO 95/10507 and Agrow No. 347, 3.3.2000, page 22 (PJB Publications Ltd. 2000). Preferred compounds of the formula (II) and their salts are 3-(4-methoxymethyl-1,3,5-triazinyl)(2-methoxycarbonyl iodophenyl-sulfonyl)urea (iodosulfuron-methyl, B1-1) and its salts, such as the sodium salt idodosulfuronmethyl-sodium , B1-2) (see, for example, WO 92/13845 and PM, pp. 547-548).

Preferred (C) compounds are selected from (C-1) methyl 4-[(4,5-dihydromethoxymethyloxo-1H-1,2,4-triazolyl)carbonylsulfamoyl] methylthiophenecarboxylate, having the ISO name thienecarbazone-methyl (CAS No.317815 1),(C1-1) described in WO 01/05788.

H C CH 3 O N N 3 O N S CH 3 (III) and its salts, preferably its sodium salt (C1-2); (C-2) N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidinyl)methoxy(trifluoromethyl) pyridinesulfonamide, having the ISO name ulam (CAS no. 9) (C2-1) and its salts or esters; (C-3) 4-aminochloro(4-chlorofluoromethoxyphenyl)pyridinecarboxylic acid, having the ISO name halauxifen (CAS no. 9438328) (C3-1) and its salts or esters, preferably halauxifen-methyl ester (CAS no. 9438319) (C3-2).

(C-4) 8-(2,6-diethylmethylphenyl)-1,2,4,5-tetrahydrooxo-7H-pyrazolo[1,2-d][1,4,5]oxadiazepinyl 2,2-dimethylpropanoate having the ISO name pinoxaden (CAS no. 2439738) (C4-1) and its salts or esters; (C-5) 3-[[[5-(difluoromethoxy)methyl(trifluoromethyl)-1H-pyrazolyl]methyl]sulfonyl]-4,5- o-5,5-dimethylisoxazole having the ISO name pyroxasulfone (CAS no. 4473995) (C5-1) and its salts or ; The abovementioned active compounds (A) and (B) and their salts are capable of inhibiting the enzyme acetolactate synthase (ALS) and thus protein synthesis in plants. The application rate of the active compounds of the formulae (A), (B) and (C) and/or their salts can be varied within a wide range, for example between 0.001 and 0.5 kg of AS/ha, preferably 0.010 and 0.100 kg of AS/ha, most preferably 0.035 to 0.05. kgAS/ha.

The abbreviation AS/ha used in this description means "active substance per hectare", based on 100% active compound. In the case of ations at ation rates of 0.01 to 0.2 kg of AS/ha of the active compounds (A) and (B) and their salts, preferably the active compounds (A1-1), (A1-2), (B1-1) and (B1-2), a relatively broad spectrum of annual and perennial broad-leaved weeds, weed grasses and Cyperacea is lled pre- and post-emergence. In the combinations according to the invention, the application rates are generally lower, for example in the range from 0.1 to 100 g of AS/ha, preferably from 0.5 to 50 g of AS/ha.

In a red embodiment of the invention (C-1) thienecarbazone-methyl and/or its salts is applied at a rate of 0.005 to 0.020 kg of AS/ha, preferably 0.007 to 0.015 kg of AS/ha, most preferably 0.0075 to 0.010 kg of AS/ha; (C-2) pyroxsulam and/or its salts or esters is applied at a rate of 0.005 to 0.050 kg of AS/ha, preferably 0.010 to 0.025 kg of AS/ha, most preferably 0.018 to 0.020 kg of AS/ha; (C-3) halauxifen and/or its salts or esters is d at a rate of 0.005 to 0.020 kg of AS/ha, preferably 0.005 to 0.015 kg of AS/ha, most preferably 0.008 to 0.010 kg of AS/ha; (C-4) pinoxaden and/or its salts or esters is d at a rate of 0.005 to 0.100 kg of AS/ha, preferably 0.050 to 0.080 kg of AS/ha, most preferably 0.060 to 0.065 kg of AS/ha; (C-5) pyroxasulfone and/or its salts or esters is applied at a rate of 0.050 to 0.500 kg of AS/ha, preferably 0.080 to 0.250 kg of AS/ha, most preferably 0.100 to 0.150 kg of AS/ha.

The active compounds can generally be formulated as water-soluble wettable powders (WP), ispersible granules (WDG), water-emulsifiable granules (WEG), suspoemulsion (SE), oil suspension concentrate (SC) or oil dispersion (OD).

The weight ratio of the components A and B to one another is between 10:1 to 1:10 preferably 8:1 to 1:2, most preferably 5:1 to 1:1.

The ratios of the application rates (A + B) : C which are generally used are stated hereinabove and identify the weight ratio of the two components (A + B) and C to each other is lly 5:1 to 1:5, preferably 4:1 to 1:2, and most preferably 1.5 :1 to 1:1.

The preferred weight ratio of the two components (A + B) and (C-1) to each other is advantageously 5:1 to 1:3, preferably 4:1 to 1:2, more ably 3:1 to 1:1, and most preferably 5:2 to 3:2.

The red weight ratio of the two components (A + B) and (C-2) to each other is advantageously 3:1 to 1:4, preferably 2:1 to 1:3, more preferably 3:2 to 2:5, and most preferably 1:1 to 1:2.

The red weight ratio of the two components (A + B) and (C-4) to each other is advantageously 2:1 to 1:5, preferably 3:2 to 1:5, more ably 1:1 to 1:4, and most preferably 1:2 to 1:4.

For use of the active compounds of the formulae (I) and (II) or their salts in plant crops, it is expedient, depending on the plant crop, to apply a safener from certain application rates upward in order to reduce or to avoid possible damage to the crop plants. Examples of suitable safeners are those which have a safener action in combination with sulfonylurea herbicides, preferably phenylsulfonylureas. le safeners are disclosed in WO-A-96/14747 and the literature cited therein.

The following groups of compounds are examples of suitable safeners for the entioned herbicidally active compounds (A) and (B): a) Compounds of the dichlorophenylpyrazolinecarboxylic acid (S1) type, preferably compounds such as ethyl 1-(2,4-dichlorophenyl)(ethoxycarbonyl)methylpyrazolinecarboxylate (S1-1, mefenpyr-diethyl, PM, pp. 594-595), and related compounds as they are described for example in WO 91/07874 and PM (pp.594-595). b) Dichlorophenylpyrazolecarboxylic acid derivatives, ably compounds such as ethyl 1-(2,4-dichlorophenyl)methylpyrazolecarboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)isopropylpyrazolecarboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)(1,1-dimethyl-ethyl)pyrazole carboxylate (S1-4), ethyl 1-(2,4-dichlorophenyl)phenylpyrazole carboxylate (S1-5) and related nds as are described in EP-A-333 131 and EP-A-269 806. c) Compounds of the triazolecarboxylic acid (S1) type, preferably compounds such as fenchlorazole, i.e. ethyl 1-(2,4-dichlorophenyl)trichloromethyl-(1H)-1,2,4-triazolecarboxylate (S1-6) and related compounds (see 74 562 and EP-A-346 620). d) Compounds of the 5-benzyl- or 5-phenylisoxazolinecarboxylic acid type or of the 5,5-diphenyl- 2-isoxazolinecarboxylic acid type, preferably nds such as ethyl 5-(2,4-dichlorobenzyl) isoxazolinecarboxylate (S1-7) or ethyl 5-phenylisoxazolinecarboxylate (S1-8) and related compounds as are described in WO 91/08202, or of ethyl 5,5-diphenylisoxazolinecarboxylate (S1-9, isoxadifen-ethyl) or n-propyl 5,5-diphenylisoxazolinecarboxylate (S1-10) or ethyl -(4-fluorophenyl)phenylisoxazolinecarboxylate (S1-11), as are described in patent application (WO-A-95/07897). e) Compounds of the 8-quinoline oxyacetic acid (S2) type, preferably 1-methylhexyl oroquinolinoxy)acetate (S2-1, cloquintocet-mexyl, e.g. PM (pp. 6), imethylbutyl) (5-chloroquinolinoxy)acetate (S2-2), 4-allyloxybutyl (5-chloroquinolinoxy)acetate (S2-3), 1-allyloxypropyl (5-chloroquinolinoxy)acetate (S2-4), ethyl (5-chloroquinolinoxy)acetate (S2-5), methyl (5-chloroquinolinoxy)acetate (S2-6), allyl (5-chloroquinolinoxy)acetate (S2-7), 2-(2-propylideneiminooxy)ethyl oroquinolinoxy)acetate (S2-8), 2-oxopropyl (5-chloroquinolinoxy)acetate (S2-9) and related compounds as are described in EP-A-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-0 492 366. f) Compounds of the (5-chloroquinolinoxy)malonic acid type, preferably compounds such as diethyl (5-chloroquinolinoxy)malonate, diallyl (5-chloroquinolinoxy)malonate, methyl ethyl (5-chloroquinolinoxy)-malonate and related compounds as are described in EP-A-0 582 198. g) Active compounds of the phenoxyacetic acids, ypropionic acids or aromatic carboxylic acids type, such as, for example, 2,4-dichlorophenoxyacetic acid (and esters) (2,4-D), 4-chloromethylphenoxypropionic esters (mecoprop), MCPA or 3,6-dichloromethoxybenzoic acid (and esters) (dicamba).

In many cases, the abovementioned safeners are also suitable for active compounds of group (C). In on, the following safeners are suitable for the ide combinations according to the invention: h) active compounds of the pyrimidine type, such as, for example, "fenclorim" (PM, pp. 386-387) (= 4,6-dichlorophenylpyrimidine), i) active compounds of the dichloroacetamide type, which are frequently used as pre-emergence safeners (soil-acting safeners) such as, for e, "dichloromid" (PM, pp. 270-271) (= N,N-diallyl-2,2-dichloroacetamide), "AR-29148" (= 3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidone by Stauffer), "benoxacor" (PM, pp. 74-75) (= 4-dichloroacetyl-3,4-dihydromethyl-2H-1,4-benzoxazine), "APPG-1292" (= N-allyl-N[(1,3-dioxolanyl)-methyl]dichloroacetamide by PPG Industries), "ADK-24" (= N-allyl-N-[(allylaminocarbonyl)-methyl]-dichloroacetamide by Sagro-Chem), "AAD-67" or "AMON 4660" (= 3-dichloroacetyloxaaza-spiro[4,5]decane by Nitrokemia or to), "diclonon" or "ABAS145138" or 45138" (= (= 3-dichloroacetyl-2,5,5-trimethyl-1,3- diazabicyclo[4.3.0]nonane by BASF) and "furilazol" or "AMON 13900" (see PM, 482-483) (= (RS)dichloroacetyl(2-furyl)-2,2- dimethyloxazolidone) j) active compounds of the dichloroacetone derivatives type, such as, for example, "AMG 191" (CAS Reg. No. 964203) (= 2-dichloromethylmethyl-1,3-dioxolane by Nitrokemia), k) active nds of the oxyimino compounds type which are known as seed-dressing materials such as, for example, "oxabetrinil" (PM, p. 689) (= 3-dioxolanylmethoxyimino(phenyl)acetonitrile), which is known as safener in seed dressing to t metolachlor damage, "fluxofenim" (PM, pp. 467-468) (= 1-(4-chlorophenyl)-2,2,2-trifluoroethanone O-(1,3-dioxolan- 2-ylmethyl)-oxime, which is known as safener in seed dressing to prevent metolachlor damage, and "cyometrinil" or "A-CGA-43089" (PM, p. 983) (= (Z)-cyanomethoxyimino(phenyl)acetonitrile), which is known as safener in seed dressing to t metolachlor damage, l) active compounds of the thiazolecarboxylic esters type, which are known as ressing materials, such as, for example, "flurazol" (PM, pp. 450-451) (= benzyl rotrifluoromethyl-1,3-thiazolecarboxylate), which is known as r in seed dressing to prevent alachlor and metolachlor damage, m) active compounds of the naphthalenedicarboxylic acid derivatives type which are known as seeddressing agents, such as, for example, "naphthalic anhydride" (PM, pp. 1009-1010) (= phthalenedicarboxylic anhydride), which is known as safener for maize in seed dressing to t thiocarbamate herbicide damage, n) active nds of the chromaneacetic acid derivatives type, such as, for example, "ACL 304415" (CAS Reg. No. 315418) (= 2carboxychromanyl)acetic acid by American Cyanamid), o) active compounds which, in addition to a herbicidal action against harmful plants, also have a safener action on crop plants, such as, for example, "dimepiperate" or "AMY-93" (PM, pp. 302-303) (= Smethylphenylethyl piperidine carbothioate), "daimuron" or "ASK 23" (PM, p. 247) (= 1-(1-methylphenylethyl)p-tolylurea), "cumyluron" = 40" (= 3-(2-chlorophenylmethyl)(1-methylphenyl-ethyl)urea, see JP-A- 54), "methoxyphenon" or "ANK 049" (= imethylmethoxy- benzophenone), "CSB" (= 1-bromo(chloromethylsulfonyl)benzene) (CAS Reg. No. 540914 by Kumiai).

The herbicides (A) and (B), if appropriate in the presence of safeners (the combination (A1-2) + (S1-1), for example, is commercially available as Sigma® OD, and the combination (A1-2) + (B1 -2) + (S1 -1) as Atlantis® WG), are suitable for controlling harmful plants in plant crops, for example in economically important crops such as cereals (such as wheat, barley, rye, oats, rice, corn, millet), sugar beet, sugar cane, oilseed rape, cotton and soybeans. Of particular interest is the application in monocotyledonous crops such as cereals, for e wheat, barley, rye, oats, in particular hybrids thereof such as triticale, rice, corn and millet. These crops are also preferred for the combinations (A)+(B)+(C).

Also included according to the invention are those herbicide ations which, in addition to components (A), (B) and (C), also comprise one or more further agrochemically active compounds of a different structure, such as herbicides, insecticides, fungicides or safeners. To such combinations, the preferred conditions illustrated below in particular for combinations (A) + (B) + (C) according to the invention also primarily apply, if they comprise the ations (A) + (B) + (C) according to the invention, and with respect to the combination (A) + (B) + (C) in question.

Of particular interest are herbicidal compositions according to the t invention and the use of herbicidal compositions according to the present invention comprising the following compounds (A) + (B) + (C), preferably mixtures or itions comprising the active compounds (A), (B) and (C) er: (A1-1) + (B1-1) + (C1-1), (A1-2) + (B1-1) + (C1-1); (A1-1) + (B1-2) + (C1-1); (A1-2) + (B1-2) + (C1-1); (A1-1) + (B1-1) + (C1-2), (A1-2) + (B1-1) + (C1-2); (A1-1) + (B1-2) + ; (A1-2) + (B1-2) + (C1-2); (A1-1) + (B1-1) + (C2-1), (A1-2) + (B1-1) + (C2-1); (A1-1) + (B1-2) + (C2-1); (A1-2) + (B1-2) + (C2-1); (A1-1) + (B1-1) + , (A1-2) + (B1-1) + (C3-1); (A1-1) + (B1-2) + (C3-1); (A1-2) + (B1-2) + (C3-1); (A1-1) + (B1-1) + , (A1-2) + (B1-1) + (C3-2); (A1-1) + (B1-2) + (C3-2); (A1-2) + (B1-2) + (C3-2); (A1-1) + (B1-1) + (C4-1), (A1-2) + (B1-1) + (C4-1); (A1-1) + (B1-2) + (C4-1); (A1-2) + (B1-2) + (C4-1); (A1-1) + (B1-1) + (C5-1), (A1-2) + (B1-1) + (C5-1); (A1-1) + (B1-2) + (C5-1); (A1-2) + (B1-2) + (C5-1).

In addition, each of the herbicide combinations mentioned above (preferably the mixtures or compositions comprising the active compounds (A), (B) and (C) together) may additionally comprise one or more rs, in particular a safener such as yr-diethyl (S1-1), isoxadifen-ethyl (S1-9) and cloquintocet-mexyl (S2- 1). Preference is in each case given to the ranges of application rates and ratios of application rates mentioned above. Examples of this are the herbicide combinations listed below.

(A1-1) + (B1-1) + (C1-1) + (S1-1), (A1-2) + (B1-1) + (C1-1) + (S1-1); (A1-1) + (B1-2) + (C1-1) + (S1-1); (A1-2) + (B1-2) + (C1-1) + (S1-1); (A1-1) + (B1-1) + (C1-2) + (S1-1), (A1-2) + (B1-1) + (C1-2) + (S1-1); (A1-1) + (B1-2) + (C1-2) + (S1-1); (A1-2) + (B1-2) + (C1-2) + (S1-1); (A1-1) + (B1-1) + (C2-1) + (S1-1), (A1-2) + (B1-1) + (C2-1) + (S1-1); (A1-1) + (B1-2) + (C2-1) + (S1-1); (A1-2) + (B1-2) + (C2-1) + (S1-1); (A1-1) + (B1-1) + (C3-1) + (S1-1), (A1-2) + (B1-1) + (C3-1) + (S1-1); (A1-1) + (B1-2) + (C3-1) + (S1-1); (A1-2) + (B1-2) + (C3-1) + (S1-1); (A1-1) + (B1-1) + (C3-2) + , (A1-2) + (B1-1) + (C3-2) + (S1-1); (A1-1) + (B1-2) + (C3-2) + ; (A1-2) + (B1-2) + (C3-2) + (S1-1); (A1-1) + (B1-1) + (C4-1) + (S1-1), (A1-2) + (B1-1) + (C4-1) + (S1-1); (A1-1) + (B1-2) + (C4-1) + (S1-1); (A1-2) + (B1-2) + (C4-1) + (S1-1); (A1-1) + (B1-1) + (C5-1) + (S1-1), (A1-2) + (B1-1) + (C5-1) + (S1-1); (A1-1) + (B1-2) + (C5-1) + (S1-1); (A1-2) + (B1-2) + (C5-1) + (S1-1); (A1-1) + (B1-1) + (C1-1) + (S1-9), (A1-2) + (B1-1) + (C1-1) + (S1-9); (A1-1) + (B1-2) + (C1-1) + ; (A1-2) + (B1-2) + (C1-1) + (S1-9); (A1-1) + (B1-1) + (C1-2) + (S1-9); (A1-2) + (B1-1) + (C1-2) + ; (A1-1) + (B1-2) + (C1-2) + (S1-9); (A1-2) + (B1-2) + (C1-2) + (S1-9); (A1-1) + (B1-1) + (C2-1) + (S1-9); (A1-2) + (B1-1) + (C2-1) + (S1-9); (A1-1) + (B1-2) + (C2-1) + (S1-9); (A1-2) + (B1-2) + (C2-1) + (S1-9); (A1-1) + (B1-1) + (C3-1) + (S1-9); (A1-2) + (B1-1) + (C3-1) + (S1-9); (A1-1) + (B1-2) + (C3-1) + (S1-9); (A1-2) + (B1-2) + (C3-1) + (S1-9); (A1-1) + (B1-1) + (C3-2) + (S1-9); (A1-2) + (B1-1) + (C3-2) + (S1-9); (A1-1) + (B1-2) + (C3-2) + (S1-9); (A1-2) + (B1-2) + (C3-2) + (S1-9); (A1-1) + (B1-1) + (C4-1) + ; (A1-2) + (B1-1) + (C4-1) + (S1-9); (A1-1) + (B1-2) + (C4-1) + ; (A1-2) + (B1-2) + (C4-1) + (S1-9); (A1-1) + (B1-1) + (C5-1) + (S1-9); (A1-2) + (B1-1) + (C5-1) + (S1-9); (A1-1) + (B1-2) + (C5-1) + (S1-9); (A1-2) + (B1-2) + (C5-1) + (S1-9); (A1-1) + (B1-1) + (C1-1) + (S2-1); (A1-2) + (B1-1) + (C1-1) + (S2-1); (A1-1) + (B1-2) + (C1-1) + (S2-1); (A1-2) + (B1-2) + (C1-1) + (S2-1); (A1-1) + (B1-1) + (C1-2) + ; (A1-2) + (B1-1) + (C1-2) + (S2-1); (A1-1) + (B1-2) + (C1-2) + (S2-1); (A1-2) + (B1-2) + (C1-2) + (S2-1); (A1-1) + (B1-1) + (C2-1) + (S2-1); (A1-2) + (B1-1) + (C2-1) + (S2-1); (A1-1) + (B1-2) + (C2-1) + (S2-1); (A1-2) + (B1-2) + (C2-1) + (S2-1); (A1-1) + (B1-1) + (C3-1) + (S2-1); (A1-2) + (B1-1) + (C3-1) + (S2-1); (A1-1) + (B1-2) + (C3-1) + (S2-1); (A1-2) + (B1-2) + (C3-1) + (S2-1); (A1-1) + (B1-1) + (C3-2) + (S2-1); (A1-2) + (B1-1) + (C3-2) + (S2-1); (A1-1) + (B1-2) + (C3-2) + (S2-1); (A1-2) + (B1-2) + (C3-2) + ; (A1-1) + (B1-1) + (C4-1) + (S2-1); (A1-2) + (B1-1) + (C4-1) + (S2-1); (A1-1) + (B1-2) + (C4-1) + (S2-1); (A1-2) + (B1-2) + (C4-1) + (S2-1); (A1-1) + (B1-1) + (C5-1) + (S2-1); (A1-2) + (B1-1) + (C5-1) + (S2-1); (A1-1) + (B1-2) + (C5-1) + (S2-1); (A1-2) + (B1-2) + (C5-1) + (S2-1).

It may be advantageous to combine one or more herbicides (A) with one or more herbicides (B) and one or more herbicides (C), for example a herbicide (A) with a herbicide (B) and one or more herbicides (C).

Herbicide combinations according to the invention with a ity of herbicide C) are, for example, those which comprise, as component C), the ing herbicide combinations: C1 + C2, which preferably comprise, as components (A) and (B), the compounds (A1-1) + (B1-1), + (B1-2), (A1-2) + (B1-1) or (A1-2) + (B1-2), in particular (A1-1) + (B1-2), and which may additionally comprise a safener, such as (S1- 1), (S1-9) or (S2-1), in ular (S1-1). Furthermore, the ations of herbicides according to the invention can be used together with other agrochemically active compounds, for example from the group of the rs, fungicides, herbicides, insecticides and plant growth regulators, or with formulation auxiliaries and additives ary in crop protection. Additives are, for example, fertilizers and colorants. Preference is in each case given to the ratios of application rates and ranges of application rates mentioned above.

The combinations according to the invention (= herbicidal compositions) have an outstanding herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. The active compounds also act efficiently on ial weeds which produce shoots from es, rootstocks or other perennial organs and which are ult to control. In this context, it does not matter r the substances are applied before sowing, pre-emergence or mergence. Post-emergence application, or early post-sowing pre-emergence application, is preferred.

Specifically, examples may be mentioned of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the combinations according to the invention, without the enumeration being a restriction to certain species.

Examples of weed species on which the idal compositions act efficiently are, from amongst the monocotyledonous weed species, for example Apera spica venti, Avena spp., Alopecurus spp., Brachiaria spp., Digitaria spp., Lolium spp., Equinochloa spp., Panicum spp., Phalaris spp., Poa spp., Setaria spp. and also Bromus spp., such as Bromus catharticus, Bromus secalinus, Bromus erectus, Bromus um and Bromus japonicus, and Cyperus species from the annual group, and, amongst the perennial species, Agropyron, Cynodon, Imperata and Sorghum and also perennial Cyperus species.

In the case of the ledonous weed species, the spectrum of action extends to species such as, for example, Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp. such as Galium aparine, Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp., Pharbitis spp., Polygonum spp., Sida spp., Sinapis spp., Solanum spp., Stellaria spp., Veronica spp. and Viola spp., Xanthium spp., amongst the annuals, and Convolvulus, Cirsium, Rumex and Artemisia in the case of the ial weeds.

If the herbicide combinations according to the invention are applied to the soil surface before germination, then the weed seedlings are either prevented completely from emerging, or the weeds grow until they have reached the cotyledon stage but then their growth stops, and, eventually, after three to four weeks have d, they die completely.

If the active compounds are applied post-emergence to the green parts of the plants, growth likewise stops drastically a very short time after the treatment and the weed plants remain at the growth stage of the point of time of application, or they die completely after a certain time, so that in this manner competition by the weeds, which is harmful to the crop plants, is eliminated at a very early point in time and in a sustained manner.

The idal itions according to the invention are distinguished by a rapidly commencing and longlasting herbicidal action. As a rule, the rainfastness of the active compounds in the combinations according to the invention is advantageous. A particular advantage is that the s of the compounds (A), (B) and (C), which are used in the combinations and are effective, can be adjusted to such a low quantity that their soil action is optimally low. Not only does this allow them to be employed in ive crops in the first place, but groundwater and surface water contaminations are virtually avoided. The active-ingredient combination according to the invention allows the application rate of the active compounds required to be reduced considerably.

In a preferred embodiment, when herbicides of the type (A)+(B)+(C) are used jointly, superadditive (= synergistic) s are observed. This means that the effect in the combinations exceeds the expected total of the effects of the individual herbicides employed. The synergistic effects allow the application rate to be reduced, a broader um of leaved weeds and grass weeds to be controlled, the herbicidal action to take place more rapidly, the duration of action to be longer, the harmful plants to be controlled better while using only one, or few, applications, and the application period which is possible to be extended. In some cases, the use of the itions also reduces the amount of harmful ingredients, such as nitrogen or oleic acid, and their introduction into the soil.

The abovementioned properties and advantages are of benefit for weed control practice to keep agricultural crops free from undesired competing plants and thus to safeguard and/or increase the yields from the qualitative and quantitative point of view. These novel combinations markedly exceed the cal state of the art with a view to the properties described.

While the combinations according to the invention have an nding idal activity against monocotyledonous and dicotyledonous weeds, the crop plants are damaged only to a minor extent, if at all.

Moreover, some of the compositions according to the invention have outstanding growth-regulatory properties on the crop plants. They engage in the plants’ metabolism in a regulatory manner and can thus be employed for provoking directed effects on plant constituents and to facilitate ting such as for e by triggering desiccation and d growth. Moreover, they are also suitable for the general control and inhibition of undesired vegetative growth without simultaneously destroying the plants. An inhibition of vegetative growth is very important in a large number of monocotyledonous and dicotyledonous crops since yield losses as a result of lodging can thus be reduced, or ted completely.

Owing to their herbicidal and plant-growth-regulatory properties, the compositions according to the invention can be employed for controlling harmful plants in genetically modified crop plants or crop plants obtained by on/selection. These crop plants are guished as a rule by particular, advantageous properties, such as resistances to herbicidal compositions or resistances to plant diseases or ive agents of plant diseases such as particular insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific tuents. Thus, for example, transgenic plants are known whose starch content is increased or whose starch quality is altered, or those where the harvested material has a different fatty acid composition.

Conventional methods of generating novel plants which have modified properties in comparison to plants occurring to date t, for example, in traditional breeding methods and the tion of mutants (see, for example, US 5,162,602; US 4,761,373; US 4,443,971). Alternatively, novel plants with altered properties can be generated with the aid of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, the following have been described in several cases: - the modification, by inant logy, of crop plants with the aim of modifying the starch synthesized in the plants (for e WO 92/11376, WO 92/14827, WO 91/19806), - transgenic crop plants which exhibit resistances to other herbicides, for example to sulfonylureas (EP-A-0257993, US-A-5013659), - transgenic crop plants with the capability of ing Bacillus thuringiensis toxins (Bt toxins), which make the plants resistant to certain pests (EP-A-0142924, EP-A-0193259), - transgenic crop plants with a ed fatty acid composition (WO 72).

A large number of ques in molecular biology are known in principle with the aid of which novel transgenic plants with modified properties can be ted: see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene und Klone", VCH Weinheim 2nd Edition 1996 or Christou, "Trends in Plant Science" 1 (1996) 423-431).

To carry out such recombinant manipulations, nucleic acid molecules which allow mutagenesis or sequence changes by recombination of DNA sequences can be introduced into plasmids. For example, the abovementioned standard methods allow base exchanges to be d out, subsequences to be removed, or natural or synthetic sequences to be added. To connect the DNA fragments to each other, rs or linkers may be added to the fragments.

For example, the generation of plant cells with a reduced ty of a gene product can be achieved by expressing at least one ponding antisense RNA, a sense RNA for achieving a cosuppression effect or by expressing at least one suitably constructed ribosome which specifically cleaves transcripts of the abovementioned gene product.

To this end, it is possible to use DNA molecules which encompass the entire coding sequence of a gene product inclusive of any flanking sequences which may be present, and also DNA molecules which only encompass portions of the coding sequence, it being necessary for these portions to be long enough to have an nse effect in the cells. The use of DNA sequences which have a high degree of homology to the encoding sequences of a gene product, but are not completely cal to them, is also possible.

When expressing nucleic acid molecules in plants, the protein synthesized can be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for e, to link the coding region with DNA ces which ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

The transgenic plant cells can be regenerated by known techniques to give rise to intact plants. In principle, the transgenic plants can be plants of any desired plant species, i.e. not only monocotyledonous, but also dicotyledonous, plants. Thus, transgenic plants can be obtained whose properties are altered by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or the expression of heterologous (= foreign) genes or gene sequences.

The invention therefore also relates to a method of controlling red vegetation (e.g. harmful plants), preferably in plant crops such as s (e.g. wheat, barley, rye, oats, hybrids thereof such as triticale, rice, corn, millet), sugar beet, sugar cane, oilseed rape, cotton and soybeans, especially preferably in monocotyledonous crops such as cereals, for example wheat, barley, rye, oats, hybrids thereof such as triticale, rice, corn and millet, which comprises applying one or more herbicides of type (A) together with one or more herbicides of type (B) and one or more herbicides of type (C) jointly or separately, for example by the pre-emergence method, by the post-emergence method or by the ergence and the post-emergence method, to the plants, for e harmful plants, parts of these plants, plant seeds or the area where the plants grow, for example the area under ation.

The plant crops can also have been cally ed or been obtained by mutation selection and are preferably tolerant to acetolactate synthase (ALS) inhibitors.

The invention also relates to the use of the novel combinations of nds (A)+(B)+(C) for controlling harmful plants, preferably in plant crops.

The herbicidal compositions according to the invention can also be used non-selectively for controlling unwanted vegetation, for example in plantation crops, in the borders of paths, in squares, in industrial plants or in railroad instalations.

The active compound combinations according to the invention can exist not only as mixed ations of the components (A), (B) and (C), if appropriate together with further agrochemically active compounds, additives and/or customary formulation auxiliaries, which are then applied in the customary manner as a dilution with water, but also as so-called tank mixes by y diluting the separately formulated, or partially separately formulated, components with water.

The nds (A), (B) and (C) or their combinations can be formulated in various ways, depending on the prevailing biological and/or chemical-physical parameters. The following are examples of l possibilities for formulations: le powders (WP), water-soluble concentrates, emulsifiable concentrates (EC), s solutions (SL), emulsions (EW) such as oil-in-water and in-oil emulsions, sprayable solutions or emulsions, suspension concentrates (SC), oil dispersions (OD), oil- or water-based sions, suspoemulsions, dusts (DP), seed-dressing als, granules for soil application or for broadcasting, or water-dispersible granules (WG), ULV ations, microcapsules or waxes.

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

The formulation auxiliaries required, such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in s, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J.; H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J.

Wiley & Sons, N.Y. Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, lopedia of e Active ", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte" [Surface-active ethylene oxide adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.

Based on these formulations, combinations with other agrochemically active substances, such as other herbicides, fungicides or insecticides, and with safeners, fertilizers and/or growth regulators, may also be prepared, for example in the form of a ix or a tank mix.

Wettable powders able powders) are products which are mly dispersible in water and which, besides the active compound, also comprise ionic or nonionic surfactants (wetters, dispersants), for example polyoxethylated alkylphenols, polyethoxylated fatty alcohols or fatty amines, alkanesulfonates or alkylbenzenesulfonates, sodium lignosulfonate, sodium inaphthylmethane-6,6’-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltauride, in addition to a t or inert al. fiable concentrates are prepared by dissolving the active compound in an organic solvent, for e butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling ics or hydrocarbons with addition of one or more ionic or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium salts of alkylarylsulfonic acids, such as calcium dodecylbenzene sulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, an fatty acid esters, yethylene sorbitan fatty acid esters or polyoxethylene sorbitol esters.

Dusts are obtained by grinding the active compound with finely divided solid materials, for example talc, l clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension trates (SC) can be water- or oil-based. They can be prepared, for example, by wet grinding by means of commercially ble bead mills and, if appropriate, addition of further surfactants as they have already been mentioned for example above in the case of the other ation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared for example by means of stirrers, colloid mills and/or static mixers using s organic solvents and, if appropriate, further surfactants as have already been mentioned for example above in the case of the other formulation types.

Granules can be prepared either by spraying the active compound onto adsorptive, granulated inert material or by applying active compound concentrates to the surface of carriers such as sand, kaolinites or granulated inert material with the aid of binders, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils.

Suitable active compounds may also be granulated in the manner conventionally used for the production of fertilizer granules, if desired in a mixture with fertilizers. As a rule, water-dispersible granules are prepared by customary processes such as spray drying, fluidized-bed granulation, disk granulation, mixing with highspeed mixers and extrusion t solid inert material. Regarding the production of disk granules, fluidized- bed granules, extruder es and spray granules, see, for example, the s in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, page 147 et seq; "Perry's Chemical Engineer's ok", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

As regards further details on the formulation of crop protection products, see, for example, G.C. am, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S.A.

Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

As a rule, the agrochemical ations comprise 0.1 to 99 percent by weight, in particular 2 to 95% by weight, of active compounds of the types A and/or B and/or C, the following concentrations being customary, depending on the type of formulation: The active compound concentration in wettable powders is, for example, approximately 10 to 95% by weight, the remainder to 100% by weight being composed of customary formulation constituents. In the case of emulsifiable trates, the active compound concentration may amount to, for example, 5 to 80% by weight. Formulations in the form of dusts comprise, in most cases, 5 to 20% by weight of active compound, sprayable ons approximately 0.2 to 25% by weight of active compound. In the case of granules such as dispersible granules, the active nd content depends partly on whether the active compound is present in liquid or solid form and on which granulation auxiliaries and fillers are being used. As a rule, the content amounts to between 10 and 90% by weight in the case of the water-dispersible granules.

In on, the abovementioned active compound formulations may comprise, if appropriate, the conventional ves, wetters, dispersants, emulsifiers, preservatives, antifreeze agents, solvents, fillers, colorants, carriers, antifoams, evaporation inhibitors, pH regulators or viscosity regulators.

The herbicidal action of the herbicide combinations ing to the invention can be improved, for example, by surfactants, preferably by wetters from the group of the fatty alcohol polyglycol ethers. The fatty alcohol polyglycol ethers preferable contain 10 – 18 carbon atoms in the fatty alcohol l and 2 – 20 ethylene oxide units in the polyglycol ether moiety. The fatty alcohol polyglycol ethers can be ic or ionic, for example in the form of fatty alcohol ycol ethers sulfates, which can be used, for example, as alkali metal salts (e.g. sodium salts or potassium salts) or um salts, but also as alkaline earth metal salts such as ium salts, such as sodium C12/C14-fatty alcohol diglycol ether sulfate (Genapol® LRO, Clariant); see, for example, 476555, EP-A-0048436, EP-A-0336151 or US-A-4,400,196 and also Proc. EWRS Symp. "Factors Affecting Herbicidal Activity and Selectivity", 227 - 232 (1988). Nonionic fatty alcohol polyglycol ethers are, for example, (C10-C18)-, preferably (C10-C14)-fatty alkohol ycol ethers containing 2 – 20, ably 3 – 15, ethylene oxide units (e.g. isotridecyl alcohol polyglycol ether), for example from the Genapol® series, such as Genapol® X-030, Genapol® X-060, l® X-080 or l® X-150 (all from Clariant GmbH).

The present invention furthermore embraces the combination of herbicides (A), (B) and (C) with the wetting agents mentioned above from the group of the fatty alcohol polyglycolethers which preferably contain 10 - 18 carbon atoms in the fatty alcohol radical and 2 - 20 ethylene oxide units in the polyglycol ether moiety and which can be present in nonionic or ionic form (for example as fatty alcohol polyglycol ether sulfates).

Preference is given to C12/C14-fatty alcohol diglycol ether sulfate sodium (Genapol® LRO, Clariant); and isotridecyl alcohol polyglycol ether with 3 - 15 ne oxide units, for example from the Genapol® X series, such as Genapol® X-030, Genapol® X-060, Genapol® X-080 or Genapol® X-150 (all from Clariant GmbH). It is furthermore known that fatty l ycol ethers such as nonionic or ionic fatty alcohol polyglycol ethers (for example fatty alcohol polyglycol ether sulfates) are also suitable for use as ants and activity enhancers for a number of other herbicides, inter alia also for herbicides from the group of the imidazolinones (see, for example, EP-A-0502014).

Moreover, it is known that fatty alcohol polyglycol ethers such as nonionic or ionic fatty alcohol polyglycol ethers (for example fatty alcohol polyglycol ether sulfates) are also suitable as penetrants and synergists for a number of other herbicides, inter alia also herbicides from the group of the imidazolinones; (see, for example, EP-A-0502014).

The herbicidal effect of the herbicide combinations according to the invention can also be increased using ble oils. The term vegetable oils is to be understood as meaning oils from oil-plant species, such as soya oil, rapeseed oil, corn oil, sunflower oil, seed oil, linseed oil, t oil, palm oil, safflower oil or castor oil, in particular rapeseed oil, and their transesterification products, for example alkyl esters, such as rapeseed oil methyl ester or rapeseed oil ethyl ester.

The vegetable oils are preferably esters of C10-C22-, preferably C12-C20-fatty acids. The 2-fatty acid esters are, for example, esters of unsaturated or saturated C10-C22-fatty acids, in particular those with an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and, in particular, C18-fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.

Examples of C10-C22-fatty acid esters are esters obtained by ng glycerol or glycol with the C10-C22-fatty acids as they exist, for example in oils from oil-plant species, or C1-C20-alkyl-C10C22-fatty acid esters as can be obtained, for example, by transesterification of the abovementioned glycerol- or glycol-C10-C22-fatty acid esters with C1-C20-alcohols (for example methanol, ethanol, propanol or l). Transesterification can be carried out by known methods as are described, for example, in Römpp Chemie Lexikon, 9th n, volume 2, page 1343, Thieme Verlag Stuttgart.

Preferred C1-C20-alkyl-C10-C22-fatty acid esters are the , ethyl, propyl, butyl, 2-ethylhexyl and dodecyl esters. Preferred glycol- and ol-C10-C22-fatty acid esters are the uniform or mixed glycol esters and ol esters of C10-C22-fatty acids, in particular those fatty acids which have an even number of carbon atoms, for example erucic acid, lauric acid, palmitic acid and, in particular, C18-fatty acids such as stearic acid, oleic acid, linolic acid or linolenic acid.

The vegetable oils can be present in the herbicidal compositions according to the invention for example in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil such as ® (Victorian Chemical Company, lia, below termed Hasten, main tuent: rapeseed oil ethyl ester), Actirob®B (Novance, France, hereinbelow termed ActirobB, main constituent: rapeseed oil methyl ester), Rako-Binol® (Bayer AG, Germany, termed Rako-Binol below, main constituent: rapeseed oil), Renol® (Stefes, Germany, termed Renol hereinbelow, vegetable oil constituent: rapeseed oil methyl ester), or Stefes Mero® (Stefes, Germany, hereinbelow termed Mero, main constituent: rapeseed oil methyl .

In a further embodiment, the present invention embraces combinations of ides (A), (B) and (C) with the vegetable oils mentioned above, such as rapeseed oil, ably in the form of commercially available oil- containing formulation ves, in particular those based on rapeseed oil such as Hasten® (Victorian Chemical Company, Australia, hereinbelow termed Hasten, main constituent: rapeseed oil ethyl ester), Actirob®B (Novance, France, hereinbelow termed ActirobB, main constituent: rapeseed oil methyl ester), Rako-Binol® (Bayer AG, Germany, termed Rako-Binol hereinbelow, main constituent: rapeseed oil), Renol® s, Germany, termed Renol hereinbelow, vegetable oil constituent: ed oil methyl ester), or Stefes Mero® (Stefes, Germany, hereinbelow termed Mero, main constituent: rapeseed oil methyl ester).

For use, the formulations, which are present in commercially available form, are optionally diluted in the customary manner, for e using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in the form of dusts, soil es, granules for broadcasting and sprayable solutions are usually not diluted further with other inert substances prior to use.

The active compounds can be applied to the plants, parts of the plants, seeds of the plants or the area under cultivation (soil of a field), preferably to the green plants and parts of the plants and, if riate, onally to the soil of the field.

One possible use is the joint application of the active compounds in the form of tank mixes, the trated ations of the individual active compounds, in optical formulations, jointly being mixed with water in the tank and the resulting spray mixture being applied.

A joint herbicidal formulation of the combination according to the invention of the active compounds (A), (B) and (C) has the advantage of being easier to apply since the quantities of the components are already presented in the correct ratio to each other. er, the adjuvants in the formulation can be matched optimally to each other.

A. General formulation es a) A dust is obtained by mixing 10 parts by weight of an active compound / active compound mixture and 90 parts by weight of talc as inert material 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 an active compound / active compound mixture, 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetter and dispersant, and grinding the mixture in a pinned-disk mill. c) A dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of an active nd / active compound mixture with 6 parts by weight of alkylphenol polyglycol ether (® Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example approx. 255 to 277°C), and grinding the e in a ball mill to a fineness of below 5 s. d) An emulsifiable concentrate is obtained from 15 parts by weight of an active compound / active compound mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxethylated nonylphenol as emulsifier. e) Water-dispersible granules are obtained by mixing 75 parts by weight of an active compound / active compound mixture, parts by weight of calcium lignosulfonate, parts by weight of sodium lauryl e, 3 parts by weight of nyl 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 spraying on water as granulation liquid. f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill, parts by weight of an active compound / active compound mixture, parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, 2 parts by weight of sodium oleoylmethyltaurinate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water, subsequently grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a single-substance nozzle.

A1. Specific formulation examples A1.a A water-dispersible granules (WG) formulation was prepared containing the following active ingredients, the balance being inert materials: 45 g/kg lfuron-methyl (A1-1) 9 g/kg Iodosulfuron-methyl-sodium (B1-2) 22.5 g/kg Thienecarbazone-methyl (C1-1) 135 g/kg Mefenpyr-diethyl (S1-1) A1.b An oil dispersion (OD) ation was prepared containing the following active ingredients, the balance being inert materials: 10 g/l Mesosulfuron-methyl-sodium (A1-2) 2 g/l lfuron-methyl-sodium (B1-2) g/l Thienecarbazone-methyl (C1-1) g/l Mefenpyr-diethyl (S1-1) B. Biological Examples Herbicidal action (outdoor ) The seeds or rhizome pieces of typical harmful plants were planted and grown under l outdoor conditions. After the harmful plants had d, they were treated, as a rule at the 2- to 4-leaf stage, with various dosages of the compositions according to the ion at a water application rate of 100 to 400 l/ha (converted).

After the treatment (approx. 4 - 6 weeks after application), the herbidical activity of the active compounds or active compound mixtures was scored visually by comparing the d plots with the untreated l plots.

Damage and development of all above-ground parts of the plants was recorded. Scoring was done on a percentage scale (100% action = all plants dead; 50% action = 50% of the plants and green plant parts dead; 0% action = no discernible action = like control plot). The score figures of in each case 4 plots were averaged.

The growth stages of the different weed species are indicated according to the BBCH monograph "Growth stages of mono-and dicotyledonous plants", 2nd edition, 2001, ed. Uwe Meier, Federal Biological Research Centre for Agriculture and Forestry (Biologische Bundesanstalt für Land und Forstwirtschaft). The respective BBCH stages are indicated in brackets for the different weed species.

The dose rates of herbicidal ingedients used in each case are indicated for the respective active ingredient in brackets and refer to the amount of active ingredient per hectare (g/ha).

The following abbreviations for the active ient are used in the Tables below: MSM: Mesosulfuron-methyl (A1-1) or Mesosulfuron-methyl-sodium (A1-2) IMS: Iodosulfuron-methyl (B1-1) or Iodosulfuron-methyl-sodium (B1-2) TCM: Thienecarbazone-methyl (C1-1) PXD: Pinoxaden PYX: Pyroxsulam HALXF: Halauxifen The herbicidal effects ed for the herbicide (mixtures) are indicated in % Activity against the respective weed. The % Damage indicated refers to the m damage observed in the respective crop.

The results of the ents are reflected in the Tables below, and the activity measured for the independent use of the active compounds (A + B) + (C) is stated in brackets. The treatments were d out using Mesosulfuron-methyl (A1-1) or Mesosulfuron-methyl-sodium (A1-2) as component (A), and Iodosulfuron- methyl (B1-1) or Iodosulfuron-methyl-sodium (B1-2) as component (B). The results of the treatments in these cases were essentially identical.

Table 1A: Combination MSM+IMS+TCM In the crop TRZDU: Triticum um (durum wheat) the following weeds were treated (field trials).

Weed (MSM+IMS) TCM (MSM+IMS) + TCM (BBCH stage) (15 + 3 g/ha) 7.5 g/ha (15 + 3 g/ha) + 7.5 g/ha % Activity % Damage % Activity % Damage % Activity % Damage PAPRH (15) 90 0 70 0 99 (90+70) 0 PICEC (22) 85 2 69 5 92 (85+69) 5 AVEST (23) 63 0 33 0 100 (63+33) 0 LOLMU (23) 72 0 43 0 98 (72+43) 0 LOLRI (29) 80 5 52 5 100 (80+52) 0 Weeds treated BBCH stage (cf. Tables 1A and 1B) PAPRH: Papaver rhoeas 15: 5 true leaves PICEC: Picris echioides 22: 2 tillers e / 2 side shoots visible AVEST: Avena is 23: 3 s visible / 3 side shoots visible LOLMU: Lolium multiflorum 23: 3 tillers visible / 3 side shoots visible LOLRI: Lolium rigidum 29: 9 or more tillers visible / 2 or more side shoots visible Table 1B: Combination MSM+IMS+TCM In the crop TRZDU: Triticum aestivum (durum wheat) the following weeds were treated (field ).

The same weed species were treated at the BBCH growth stages as in the case of Table 1A, however here a different ratio of MSM : IMS was used.

Weed (MSM+IMS) TCM (MSM+IMS) + TCM (BBCH stage) ( 9 + 9 g/ha) 7.5 g/ha (9 + 9 g/ha) + 7.5 g/ha % Activity % Damage % Activity % Damage % Activity % Damage PAPRH (15) 87 0 70 0 98 (87+70) 0 PICEC (22) 97 5 69 5 99 (97+69) 10 AVEST (23) 63 0 33 0 70 (63+33) 0 LOLMU (23) 65 0 43 0 88 (65+43) 0 LOLRI (29) 63 5 52 5 74 (63+52) 10 Table 2A: Combination MSM+IMS+TCM In the crop TRZAW: Triticum aestivum (soft wheat) the following weeds were treated (field trials).

Weed (MSM+IMS) TCM (MSM+IMS) + TCM (BBCH stage) (15 + 3 g/ha) 7.5 g/ha (15 + 3 g/ha) + 7.5 g/ha % Activity % Damage % Activity % Damage % Activity % Damage CENCY (19) 25 1 38 0 92 (25+38) 0 GALAP (23) 82 0 37 0 95 (82+37) 0 GERDI (29) 43 1 63 0 98 (43+63) 0 LAMAM (32) 75 10 68 1 99 (75+68) 7 LAMPU (61) 78 10 70 1 96 (78+70) 7 MATIN (19) 87 0 20 0 100 (87+20) 0 VERPE 72 10 10 1 90 ) 7 VIOAR (15) 43 1 38 0 84 (43+38) 0 Weeds treated BBCH stage (cf. Tables 2A and 2B) CENCY: rea Cyanus 19: 9 or more true leaves GALAP: Galium aparine 23: 3 tillers visible / 3 side shoots visible GERDI: Geranium tum 29: 9 or more tillers visible / 2 or more side shoots visible LAMAM: Lamium amplexicaule 32: Stem (rossete) 20% of final length (diameter) / 2 node LAMPU: Lamium eum 61: Beginning of flowering: 10% flowers open MATIN: Matricaria inodora 19: 9 or more true leaves VERPE: Veronica persica VIOAR: Viola arvensis 15: 5 true leaves Table 2B: Combination MSM+IMS+TCM In the crop TRZAW: Triticum aestivum (soft wheat) the following weeds were treated (field trials).

The same weed species were treated at the BBCH growth stages as in the case of Table 2A, r here a different ratio of MSM : IMS was used.

Weed (MSM+IMS) TCM (MSM+IMS) + TCM (BBCH stage) (9 + 9 g/ha) 7.5 g/ha (9 + 9 g/ha) + 7.5 g/ha % Activity % Damage % Activity % Damage % Activity % Damage CENCY (19) 37 2 38 0 93 (37+38) 1 GALAP (23) 88 0 37 0 91 (88+37) 0 GERDI (29) 91 2 63 0 98 (91+63) 0 LAMAM (32) 88 3 68 1 93 (88+68) 13 LAMPU (61) 88 3 70 1 95 (88+70) 13 MATIN (19) 92 0 20 0 93 ) 0 VERPE 78 3 10 1 94 (78+10) 13 VIOAR (15) 85 2 38 0 96 (85+38) 1 Table 3: Combination S+PXD In the crop TRZAW: Triticum aestivum (soft wheat) the following weeds were treated (field trials).

Weed (MSM+IMS) PXD (MSM+IMS) + PXD (BBCH stage) (15 + 3 g/ha) 60 g/ha (15 + 3 g/ha) + 60 g/ha % Activity % Damage % Activity % Damage % Activity % Damage CENCY (38) 83 0 60 15 88 (83+60) 15 GERDI (19) 68 0 30 4 78 (68+30) 1 VERHE (71) 45 0 13 0 68 (45+13) 9 VERPE (31) 33 0 0 0 53 (33+0) 0 BROST (25) 89 0 0 0 98 (89+0) 0 Weeds treated (cf. Table 3) BBCH stage CENCY: Centaurea Cyanus 38: Stem (rossete) 80% of final length (diameter) / 8 node GERDI: Geranium dissectum 19: 9 or more true leaves VERHE: Veronica hederifolia 71: 10% fruits have reached final size or 10% final size VERPE: Veronica persica 31: Stem te) 10% of final length (diameter) / 1 node BROST: Bromus sterilis 25: 5 tillers visible / 5 side shoots visible Table 4: Combination MSM+IMS+PYX Weed (MSM+IMS) PYX MS) + PYX (BBCH stage) (7.5 + 1.5 g/ha) 17 g/ha (7.5 + 1.5 g/ha) + 17 g/ha % Activity % Activity % Activity LOLRI (10) 35 20 73 (35+20) Weed treated (cf. Table 4): LOLRI: Lolium rigidum at BBCH stage 10 (1 true leaf) Table 5: Combination MSM+IMS+HALXF In the crop TRZAW: um aestivum (soft wheat) the following weeds were treated.

Weed MS) HALXF (MSM+IMS) + HALXF (9 + 1.8 g/ha) 276.5 g/ha (9 + 1.8 g/ha) + 276.5 g/ha % Activity % Damage % Activity % Damage % Activity % Damage CENCY 40 0 45 0 85 (40+45) 5 FUMOF 93 0 85 0 99 (93+85) 5 GALAP 88 0 73 0 98 (88+73) 5 PAPRH 83 0 75 0 95 (83+75) 5 Weeds treated (cf. Table 5): CENCY: Centaurea Cyanus FUMOF: Fumaria officinalis GALAP: Gallium aparine PAPRH: Papaver rhoeas

Claims (10)

Claims:

1. A herbicide combination comprising an ive amount of components (A), (B) and (C), wherein (A) s mesosulfuron-methyl (A1-1) and/or mesosulfuron-methyl sodium (A1-2); (B) denotes iodosulfuron-methyl (B1-1) and/or iodosulfuron-methyl sodium (B1-2); (C) denotes (C-4) pinoxaden; and/or salts thereof, wherein the weight ratio of the components A and B to one another is between 10:1 to 1:10 and/or the weight ratio of the two components (A + B) and C to each other is 5:1 to 1:5.

2. The herbicide combination as claimed in claim 1, which additionally comprises one or more further components selected from the group consisting of agrochemically active compounds of a different type, formulation auxiliaries and additives ary in crop protection.

3. The herbicide combination as claimed in claim 1 or 2, which additionally comprises one or more safeners.

4. The herbicide combination as claimed in claim 3, wherein the safener is mefenpyr-diethyl (S1-1).

5. The ide combination as claimed in any one of claims 1 to 4, which additionally comprises one or more fatty alcohol ycol ethers and/or one or more ble oils.

6. A method for controlling undesired plant growth which comprises applying the herbicides (A), (B) and (C) as defined in any one of claims 1 to 5 onto the plants, parts of plants, plant seeds or the area where the plants grow.

7. The method as claimed in claim 6 for the selective control of harmful plants in plant crops.

8. The method as claimed in claim 7 for the control of harmful plants in crops of monocotyledonous plants.

9. The method as claimed in claim 7 or 8 in which the plant crops are genetically modified or have been obtained by mutation/selection.

10. The use of the herbicide combination defined in any one of claims 1 to 5 for controlling l plants.