WA is an unsubstituted or substituted divalent heterocyclic moiety selected from the group of partially unsaturated or aromatic five-membered heterocycles carrying 1 to 3 hetero ring atoms selected from the group of nitrogen (N) und oxygen (O), and carrying at least one N-atom and not more than one O-atom in the ring, preferably a five-membered heterocyclic moiety selected from the group (WA¹) to (WA⁴),

mA is 0 or 1 ;

RA² is ORA³, SRA³ or NRA³RA⁴ or a saturated or unsaturated 3- to 7-membered heterocycle containing at least one N-atom and up to 3 heteroatoms, preferably combined with other heteroatoms from the group of O (oxygen) and S (sulfur), and which is linked to the carbonyl group in (SI) via a nitrogen atom, and which ist unsubstituted or substituted by moieties selected from the group of (Ci-C -alkyl, (Ci-C4)-alkoxy or possibly substituted phenyl, preferably ORA³, NHR_A⁴ Oder N(CH₃)₂, particularly ORA³

RA³ is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon moiety, preferably containing 1 to 18 C-atoms;

RA⁴ is hydrogen, (Ci-Ce)-alkyl, (Ci-Ce)-alkoxy or substituted or unsubstituted phenyl;

RA⁵ is hydrogen, (Ci-Cs)-alkyl, (Ci-Cs)-haloalkyl, (Ci-C4)-alkoxy-(Ci-Cs)-alkyl, cyano or COORA⁹, wherein RA⁹ is hydrogen, (Ci-Cs)-alkyl, (Ci-Cs)-haloalkyl, (Ci-C4)-alkoxy-(Ci-C4)-alkyl, (Ci-Ce)-hydroxyalkyl, (C3-Ci2)-cycloalkyl oder tris-(Ci-C4)-alkylsilyl;

RA⁶, RA⁷, RA⁸ are independently hydrogen, (Ci-Cs)-alkyl, (Ci-Cs)-haloalkyl, (C₃-Ci2)-cycloalkyl or substituted or unsubstituted phenyl;

RA¹⁰ is hydrogen, (C₃-Ci₂)-cycloalkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted heteroaryl;

Sl^a) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (Sl^a), preferably compounds such as l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3- carboxylic acid, ethyl l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3- carboxylate (Sl-1) ("mefenpyr-diethyl"), and related compounds as described in WO-A- 91/07874;

Sl^b) Derivatives of dichlorophenylpyrazolecarboxylic acid (Sl^b), preferably compounds such as ethyl l-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (SI -2), ethyl l-(2,4- dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (Sl-3), ethyl l-(2,4-dichlorophenyl)-5-(l,l- dimethylethyl)pyrazole-3-carboxylate (SI -4) and related compounds as described in EP-A- 333131 and EP-A-269806;

Sl^c) Derivatives of l,5-diphenylpyrazole-3-carboxylic acid (Sl^c), preferably compounds such as ethyl l-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (Sl-5), methyl l-(2- chlorophenyl)-5-phenylpyrazole-3-carboxylate (SI -6) and related compounds as described, for example, in EP-A-268554;

Sl^d) Compounds of the triazolecarboxylic acid type (Sl^d), preferably compounds such as fenchlorazole(-ethyl ester), i.e. ethyl l-(2,4-dichlorophenyl)-5-trichloromethyl-lH-l,2,4- triazole-3-carboxylate (Sl-7), and related compounds, as described in EP-A-174562 and EP-A- 346620;

Sl^e) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or of the 5,5-diphenyl- 2-isoxazoline-3-carboxylic acid type (Sl^e), preferably compounds such as ethyl 5-(2,4- dichlorobenzyl)-2-isoxazoline-3-carboxylate (SI -8) or ethyl 5-phenyl-2-isoxazoline-3- carboxylate (Sl-9) and related compounds as described in WO-A-91/08202, or 5,5-diphenyl-2- isoxazolinecarboxylic acid (Sl-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (Sl-11) ("isoxadifen-ethyl") or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (Sl-12) or ethyl 5-(4- fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S 1-13) as described in patent application WO-A-95/07897.

Sl^f) compounds of the triazolyloxy acetic acid type (Sl^f), preferably compounds such as methyl-

{[l,5-bis(4-chloro-2-fluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetate (Sl-14) or {[1,5-Bis(4- chloro-2-fluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid (Sl-15) or methyl- {[5-(4-chloro- 2-fluorophenyl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetate (Sl-16) or {[5-(4- chloro-2-fhrorphenyl)-l-(2,4-difluorophenyl)-lH-l,2,4-triazol-3-yl]oxy}acetic acid (Sl-17) or methyl- { [1 -(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)- 1H- 1 ,2,4-triazol-3-yl]oxy } acetate (S 1 - 18) or { [l-(4-chloro-2-fhrorophenyl)-5-(2,4-difluorophenyl)-lH-l,2,4-triazol-3- yl]oxy}acetic acid (S 1-19), as described in patent application WO2021105101.

S2) Compounds from the group of the 8-quinolinoxy derivatives (S2):

S2^a) Compounds of the 8-quinolinoxy acetic acid type (S2^a), preferably 1 -methylhexyl (5-chloro-8- quinolinoxy)acetate ("cloquintocet-mexyl") (S2-1), 1,3-dimethylbut-l-yl (5-chloro-8- quinolinoxy)acetate (S2-2), 4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3), 1- allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4), ethyl (5-chloro-8-quinolinoxy)acetate (S2-5), methyl (5-chloro-8-quinolinoxy)acetate (S2-6), allyl (5 -chloro- 8-quinolinoxy) acetate (S2-7), 2-(2-propylideneiminoxy)-l -ethyl (5-chloro-8-quinolinoxy)acetate (S2-8), 2-oxoprop-l- yl (5-chloro-8-quinolinoxy)acetate (S2-9) and related compounds, as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492 366, and also (5-chloro-8-quinolinoxy)acetic acid (S2-10), hydrates and salts thereof, for example the lithium, sodium, potassium, calcium, magnesium, aluminium, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts thereof, as described in WO-A-2002/34048;

S2^b) Compounds of the (5-chloro-8-quinolinoxy)malonic acid type (S2^b), preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methyl ethyl (5-chloro-8-quinolinoxy)malonate and related compounds, as described in EP-A-0 582 198.

53) Active ingredients of the dichloroacetamide type (S3), which are frequently used as preemergence safeners (soil-acting safeners), for example

"dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1),

"R-29148" (3-dichloroacetyl-2,2,5-trimethyl-l,3-oxazolidine) from Stauffer (S3-2),

"R-28725" (3-dichloroacetyl-2,2-dimethyl-l,3-oxazolidine) from Stauffer (S3-3),

"benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazine) (S3-4),

"PPG-1292" (N-allyl-N-[(l,3-dioxolan-2-yl)methyl]dichloroacetamide) from PPG Industries (S3-5),

"DKA-24" (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) from Sagro-Chem (S3- 6),

"AD-67" or "MON 4660" (3-dichloroacetyl-l-oxa-3-azaspiro[4.5]decane) from Nitrokemia or Monsanto (S3-7),

"TI-35" (1-dichloroacetylazepane) from TRI-Chemical RT (S3-8),

"diclonon" (dicyclonon) or "BAS145138" or "LAB145138" (S3-9)

((RS)-l-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[l,2-a]pyrimidin-6-one) from BASF,

"furilazole" or "MON 13900" ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3- 10), and the (R) isomer thereof (S3- 11).

54) Compounds from the class of the acylsulfonamides (S4):

S4^a) N- Acylsulfonamides of the formula (S4^a) and salts thereof, as described in WO-A-97/45016,

in which

RA¹ is (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, where the 2 latter radicals are substituted by VA substituents from the group of halogen, (Ci-C4)-alkoxy, (Ci-Ce) -haloalkoxy and (C1-C4)- alkylthio and, in the case of cyclic radicals, also by (Ci-C4)-alkyl and (Ci-C4)-haloalkyl;

RA² is halogen, (Ci-C^-alkyl, (Ci-C4)-alkoxy, CF3; mA is 1 or 2;

VA is 0, 1, 2 or 3;

S4^b) Compounds of the 4-(benzoylsulfamoyl)benzamide type of the formula (S4^b) and salts thereof, as described in WO-A-99/16744,

in which

RB¹, RB² are independently hydrogen, (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, (C3-Ce)-alkenyl, (C3- Ce)-alkynyl,

RB³ is halogen, (Ci-C^-alkyl, (Ci-C4)-haloalkyl or (Ci-C4)-alkoxy and ms is 1 or 2, e.g. those in which

RB¹ = cyclopropyl, RB² = hydrogen and (RB³) = 2-OMe ("cyprosulfamide", S4-1),

RB¹ = cyclopropyl, RB² = hydrogen and (RB³) = 5-Cl-2-OMe (S4-2),

RB¹ = ethyl, RB² = hydrogen and (RB³) = 2-OMe (S4-3),

RB¹ = isopropyl, RB² = hydrogen and (RB³) = 5-Cl-2-OMe (S4-4) and RB¹ = isopropyl, RB² = hydrogen and (RB³) = 2-OMe (S4-5);

S4^C) Compounds from the class of the benzoylsulfamoylphenylureas of the formula (S4^C), as described in EP-A-365484,

in which

Rc¹, Rc² are independently hydrogen, (Ci-Cs)-alkyl, (C3-Cs)-cycloalkyl, (C3-Ce)-alkenyl,

(C3-Ce)-alkynyl,

Rc³ is halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, CF3, and me is 1 or 2; for example l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, l-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea;

S4^d' Compounds of the N-phenylsulfonylterephthalamide type of the formula (S4^d) and salts thereof, which are known, for example, from CN 101838227,

in which

RD⁴ is halogen, (Ci-C^-alkyl, (Ci-C4)-alkoxy, CF3; mo is 1 or 2;

RD⁵ is hydrogen, (Ci-Ce)-alkyl, (C3-Ce)-cycloalkyl, (C2-Ce)-alkenyl, (C2-Ce)-alkynyl,

(C5-C6)-cycloalkenyl. 55) Active ingredients from the class of the hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives (S5), for example ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4- hydroxybenzoic acid, 3, 5 -dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxy cinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO- A-2005/015994, WO- A-2005/016001.

56) Active ingredients from the class of the 1 ,2-dihydroquinoxalin-2-ones (S6), for example 1- methyl-3-(2-thienyl)- 1 ,2-dihydroquinoxalin-2-one, 1 -methyl-3-(2-thienyl)- 1 ,2- dihydroquinoxaline-2-thione, 1 -(2-aminoethyl)-3-(2-thienyl)- 1 ,2-dihydroquinoxalin-2-one hydrochloride, 1 -(2-methylsulfonylaminoethyl)-3-(2-thienyl)- 1 ,2-dihydroquinoxalin-2-one, as described in WO- A-2005/112630.

57) Compounds from the class of the diphenylmethoxyacetic acid derivatives (S7), e.g. methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid, as described in WO-A-98/38856.

58) Compounds of the formula (S8), as described in WO- A-98/27049,

in which the symbols and indices are defined as follows:

RD¹ is halogen, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (Ci-C4)-alkoxy, (Ci-C4)-haloalkoxy,

RD² is hydrogen or (Ci-C4)-alkyl,

RD³ is hydrogen, (Ci-Cs)-alkyl, (Ci-C l-alkcnyl, (Ci-C l-alkynyl or aryl, where each of the aforementioned carbon-containing radicals is unsubstituted or substituted by one or more, preferably up to three, identical or different radicals from the group consisting of halogen and alkoxy; or salts thereof, no is an integer from 0 to 2.

S9) Active ingredients from the class of the 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), for example l,2-dihydro-4-hydroxy-l-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No.: 219479- 18-2), l,2-dihydro-4-hydroxy-l-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A- 1999/000020.

S10) Compounds of the formulae (S10^a) or (S10^b) as described in WO-A-2007/023719 and WO-A-2007/023764

in which

RE¹ is halogen, (Ci-C4)-alkyl, methoxy, nitro, cyano, CF3, OCF3,

YE, ZE are independently O or S,

HE is an integer from 0 to 4,

RE² is (Ci-Cie)-alkyl, (C2-Ce)-alkenyl, (C3-Ce)-cycloalkyl, aryl; benzyl, halobenzyl,

RE³ is hydrogen or (Ci-Ce)-alkyl. ) Active ingredients of the oxyimino compounds type (Si l), which are known as seed-dressing agents, for example

"oxabetrinil" ((Z)-l,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (SI 1-1), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage,

"fluxofenim" (l-(4-chlorophenyl)-2,2,2-trifluoro-l -ethanone O-(l,3-dioxolan-2-ylmethyl)- oxime) (SI 1-2), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage, and

"cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (SI 1-3), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage. ) Active ingredients from the class of the isothiochromanones (S12), for example methyl [(3-oxo- lH-2-benzothiopyran-4(3H)-ylidene)methoxy] acetate (CAS Reg. No. 205121-04-6) (SI 2-1) and related compounds from WO-A- 1998/13361. ) One or more compounds from group (SI 3):

"naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed-dressing safener for maize against thiocarbamate herbicide damage, "fenclorim" (4,6-dichloro-2-phenylpyrimidine) (SI 3-2), which is known as a safener for pretilachlor in sown rice,

"flurazole" (benzyl 2-chloro-4-trifluoromethyl-l,3-thiazole-5-carboxylate) (S13-3), which is known as a seed-dressing safener for millet/sorghum against alachlor and metolachlor damage,

"CL 304415" (CAS Reg. No. 31541-57-8)

(4-carboxy-3,4-dihydro-2H-l-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for maize against damage by imidazolinones,

"MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl- 1,3 -dioxolane) (S13-5) from Nitrokemia, which is known as a safener for maize,

"MG 838" (CAS Reg. No. 133993-74-5)

(2-propenyl l-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia

"disulfoton" (0,0-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7),

"dietholate" (0,0-diethyl O-phenyl phosphorothioate) (SI 3-8),

"mephenate" (4-chlorophenyl methylcarbamate) (S13-9).

S14) Active ingredients which, in addition to herbicidal action against harmful plants, also have safener action on crop plants such as rice, for example

"dimepiperate" or "MY-93" (.S'- 1 -methyl 1 -phenylethylpiperidine- 1 -carbothioate), which is known as a safener for rice against damage by the herbicide molinate,

"daimuron" or "SK 23" (l-(l-methyl-l-phenylethyl)-3-p-tolylurea), which is known as a safener for rice against damage by the herbicide imazosulfuron,

"cumyluron" = "JC-940" (3-(2-chlorophenylmethyl)-l-(l-methyl-l-phenylethyl)urea, see JP-A-

60087254), which is known as a safener for rice against damage by some herbicides,

"methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against damage by some herbicides,

“CSB" (l-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage by some herbicides in rice.

S 15) Compounds of the formula (S15) or tautomers thereof

as described in WO-A-2008/131861 and WO-A-2008/131860 in which

RH¹ is a (Ci-Ce)-haloalkyl radical and

RH² is hydrogen or halogen and

RH³, RH⁴ are independently hydrogen, (Ci-Cie)-alkyl, (C2-Cie)-alkenyl or (C2-Cie)-alkynyl, where each of the 3 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (Ci-C4)-alkoxy, (Ci-C4)-haloalkoxy, (Ci- C4)-alkylthio, (Ci-C4)-alkylamino, di[(Ci-C4)-alkyl]amino, [(Ci-C4)-alkoxy]carbonyl, [(Ci-C4)-haloalkoxy]carbonyl, (C3-C6)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or (C3-Ce)-cycloalkyl, (C4-Ce)-cycloalkenyl, (C3-Ce)-cycloalkyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (Cr-Ce)- cycloalkenyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring, and where each of the 4 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (C1-C4)- alkoxy, (Ci-C4)-haloalkoxy, (Ci-C4)-alkylthio, (Ci-C4)-alkylamino, di[(Ci-C4)- alkyl]amino, [(Ci-C4)-alkoxy]carbonyl, [(Ci-C4)-haloalkoxy]carbonyl, (Cs-Ce)- cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted,

RH³ is (Ci-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-Ce)-alkynyloxy or (C2-C4)-haloalkoxy and

RH⁴ is hydrogen or (Ci-C4)-alkyl or

RH³ and RH⁴ together with the directly attached nitrogen atom represent a four- to eightmembered heterocyclic ring which, as well as the nitrogen atom, may also contain further ring heteroatoms, preferably up to two further ring heteroatoms from the group of N, O and S, and which is unsubstituted or substituted by one or more radicals from the group of halogen, cyano, nitro, (Ci-C4)-alkyl, (Ci-C4)-haloalkyl, (Ci-C4)-alkoxy, (C1-C4) -haloalkoxy and (Ci-C4)-alkylthio.

SI 6) Active ingredients which are used primarily as herbicides but also have safener action on crop plants, for example

(2,4-dichlorophenoxy)acetic acid (2,4-D),

(4-chlorophenoxy)acetic acid,

(R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),

4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),

(4-chloro-o-tolyloxy) acetic acid (MCPA),

4-(4-chloro-o-tolyloxy)butyric acid,

4-(4-chlorophenoxy)butyric acid,

3,6-dichloro-2-methoxybenzoic acid (dicamba),

1 -(ethoxycarbonyl)ethyl 3 ,6-dichloro-2-methoxybenzoate (lactidichlor-ethyl) .

Preferred safeners in combination with the herbicide combinations of the invention are: cloquintocet- mexyl, cyprosulfamide, fenchlorazole ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.

For application, the active ingredient combinations can be deployed onto the plants (e.g. harmful plants such as mono- or dicotyledonous weeds or unwanted crop plants), the seed (e.g. grains, seeds or vegetative propagation organs such as tubers or parts of shoots having buds), or the area in which the plants grow (e.g. the growing area).

The substances can be deployed prior to sowing (if appropriate also by incorporation into the soil), prior to emergence or after emergence. Preference is given to use by the early post-seeding pre-emergence method or by the post-emergence method in plantation crops against harmful plants that have not yet emerged or have already emerged. The application can also be integrated into weed management systems with divided repeated applications (sequentials). The herbicide combination(s)/composition(s) according to the present invention have an outstanding herbicidal activity against a broad spectrum of economically important harmful monocotyledonous and dicotyledonous harmful plants.

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

In the context of the present text, reference may be made to growth stages 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 fur Land und Forstwirtschaft).

Examples of monocotyledonous harmful plants on which the herbicide combination/composition according to the present invention act efficiently are from amongst the genera Hordeum spp., Echinochloa spp., Poa spp., Bromus spp., Digitaria spp., Eriochloa spp., Setaria spp., Pennisetum spp., Phalaris sp., Eleusine spp., Eragrostis spp., Panicum spp., Lolium spp., Alopecurus sp., Apera sp. Brachiaria spp., Leptochloa spp., Avena spp., Cyperus spp., Axonopris spp., Sorghum spp., and Melinus spp..

Particular examples of monocotyledonous harmful plants species on which the herbicide combination/composition according to the present invention act efficiently are selected from amongst the species Hordeum murinum, Echinochloa crus-galli, Poa annua, Bromus rubens L., Bromus rigidus, Bromus secalinus L., Digitaria insularis, Digitaria sanguinalis, Eriochloa gracilis, Setaria faberi, Setaria viridis, Pennisetum glaucum, Eleusine indica, Eragrostis pectinacea, Panicum miliaceum, Phalaris minor, Lolium multiflorum, Lolium rigidum, Lolium perenne, Brachiaria platyphylla, Leptochloa fusca, Avena fatua, Cyperus compressus, Cyperus esculentes, Axonopris offinis, Sorghum halapense, Alopecurus myosuroides, Apera spica- venti and Melinus repens.

Examples of dicotyledonous harmful plants on which the herbicide combination/composition according to the present invention act efficiently are from amongst the genera Amaranthus spp., Polygonum spp., Medicago spp., Mollugo spp., Cyclospermum spp., Stellaria spp., Gnaphalium spp., Taraxacum spp., Oenothera spp., Amsinckia spp., Erodium spp., Erigeron spp., Senecio spp., Lamium spp., Kochia spp., Chenopodium spp., Lactuca spp., Malva spp., Ipomoea spp., Brassica spp., Sinapis spp., Urtica spp., Sida spp, Portulaca spp., Richardia spp., Ambrosia spp., Calandrinia spp., Sisymbrium spp., Sesbania spp., Capsella spp., Sonchus spp., Euphorbia spp., Helianthus spp., Coronopus spp., Salsola spp., Abutilon spp., Vicia spp., Epilobium spp., Cardamine spp., Pieris spp., Trifolium spp., Galinsoga spp., Epimedium spp., Marchantia spp., Solanum spp., Oxalis spp., Metricaria spp., Plantago spp., Tribulus spp., Cenchrus spp. Bidens spp., Veronica spp., and Hypochaeris spp.. Particular examples of dicotyledonous harmful plants species on which the herbicide combination/composition according to the present invention act efficiently are selected from amongst the species Amaranthus spinosus, Amaranthus palmer, Amaranthis rudis, Polygonum convolvulus, Medicago polymorpha, Mollugo verticillata, Cyclospermum leptophyllum, Stellaria media, Gnaphalium purpureum, Taraxacum offi cinale, Oenothera laciniata, Amsinckia intermedia, Erodium cicutarium, Erodium moschatum, Erigeron bonariensis, Senecio vulgaris, Lamium sp., Erigeron canadensis, Polygonum aviculare, Kochia scoparia, Chenopodium album, Lactuca serriola, Malva parviflora, Malva neglecta, Ipomoea hederacea, Ipomoea lacunose, Brassica nigra, Sinapis arvensis, Urtica dioica, Amaranthus blitoides, Amaranthus retroflexus, Amaranthus hybridus, Amaranthus lividus, Sida spinosa, Portulaca oleracea, Richardia scabra, Ambrosia artemisiifolia, Calandrinia caulescens, Sisymbrium irio, Sesbania exaltata, Capsella bursa-pastoris, Sonchus oleraceus, Euphorbia maculate, Helianthus annuus, Coronopus didymus, Salsola tragus, Abutilon theophrasti, Vicia benghalensis L., Epilobium paniculatum, Cardamine spp, Pieris echioides, Trifolium spp., Galinsoga spp., Epimedium spp., Marchantia spp., Solanum spp., Oxalis spp., Matricaria chamomilla, Plantago spp., Tribulus terrestris, Salsola kali, Cenchrus spp., Bidens bipinnata, Veronica sp., Galium aparine L., Papaver rhoeas, Viola arvense, Geranium, sp., Centaurea cyanus and Hypochaeris radicata.

If the active ingredient combinations of the invention are applied to the soil surface before germination, either the emergence of the weed seedlings is prevented completely or the weeds grow until they have reached the cotyledon stage, but then stop growing and ultimately die completely after three to four weeks have passed.

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

The herbicidal products of the invention are notable for a rapid onset and long duration of herbicidal action. In general, the rainfastness of the active ingredients in the combinations of the invention is favourable. A particular advantage is that the effective dosages of compounds (A) and (B) that are used in the combinations can be adjusted to such a low level that their soil action is optimally low. Therefore, the use thereof in sensitive crops is not just enabled, but groundwater contamination is also virtually prevented. The inventive combination of active ingredients allows the required application rate of the active ingredients to be reduced considerably. The combined use of herbicides (A) and (B), and optionally (C), achieves performance properties extending beyond what was to be expected on account of the known properties of the individual herbicides for the combination thereof. For example, the herbicidal effects for a particular harmful plant species exceed the expected value as can be estimated by standard methods, for example according to Colby or other extrapolation methods.

A synergistic effect exists whenever the effect, the herbicidal effect here, of the active ingredient combination is greater than the sum total of the effects of the active ingredients applied individually. The expected activity for a given combination of two active ingredients can be calculated according to S.R. Colby (“Calculating Synergistic and Antagonistic Responses of Herbicide Combinations”, Weeds 15 (1967), 20-22) (see below).

The synergistic effects therefore permit, for example, a reduction in the application rates of the individual active ingredients, a higher efficacy at the same application rate, the control of species of harmful plants which are as yet uncovered (gaps), elevated residual action, an extended period of efficacy, an elevated speed of action, an extension of the period of application and/or a reduction in the number of individual applications required and - as a result for the user - weed control systems which are more advantageous economically and ecologically.

The active ingredient combinations of the invention can preferably be used as herbicides in crops of useful plants that are resistant, or have been made resistant by genetic engineering, to the phytotoxic effects of the herbicides. The active ingredient combinations of the invention can preferably also be used in transgenic crops that are resistant to protoporphyrinogen oxidase (PPO) inhibitors and which are further resistant (a) to one or more growth regulators, for example dicamba, or (b) to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS), hydroxyphenyl-pyruvate dioxygenases (HPPD), or to herbicides from the group of the sulfonylureas, the glyphosates, glufosinates or benzoylisoxazoles and analogous active ingredients.

The invention also provides for the use of the combinations of compounds (A)+(B), and optionally (C), for control of harmful plants, optionally in crops of useful plants, preferably on uncultivated land and plantation crops, but also for control of harmful plants before the sowing of the subsequent useful plant, such as, in particular, for preparation for seeding ("burn-down application").

The active ingredient combinations of the invention may either take the form of mixed formulations of the two components, if appropriate with further active ingredients, additives and/or customary formulation auxiliaries, which are then applied in a customary manner diluted with water or can be prepared as what are called tankmixes by joint dilution of the separately formulated or partially separately formulated components with water.

The compounds (A) and (B), and optionally (C), or their combinations can be formulated in various ways according to which biological and/or physicochemical parameters are required. Examples of general formulation options are: wettable powders (WP), water-soluble powders (SP), emulsifiable concentrates (EC), water-soluble concentrates, aqueous solutions (SL), emulsions (EW), such as oil-in- water and water-in-oil emulsions, spray able solutions or emulsions, dispersions based on oil or water, oil dispersions (OD), suspoemulsions, suspension concentrates (SC), oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for soil application or scattering, granules (GR) in the form of microgranules, spray granules, absorption and adsorption granules, water- dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules or waxes. The invention therefore also provides herbicidal and plant-growth-regulating compositions containing the active ingredient combinations of the invention.

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

The necessary formulation auxiliaries such as inert materials, surfactants, solvents and further additives are likewise known and are described, for example, in: Watkins, "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. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964, Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte" ["Interface-active Ethylene Oxide Adducts"], Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Kuchler, "Chemische Technologic", Volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

On the basis of these formulations, it is also possible to produce combinations with other pesticidally active substances, such as other herbicides, fungicides, insecticides or other pesticides (for example acaricides, nematicides, molluscicides, rodenticides, aphicides, avicides, larvicides, ovicides, bactericides, viricides etc.), and also with safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or as a tank mix. Wettable powders are preparations which can be dispersed uniformly in water and, in addition to the active ingredient, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example poly oxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'- disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. To produce the wettable powders, the active herbicidal ingredients are finely ground, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.

Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or for example polyoxyethylene sorbitan fatty acid esters.

Dusting products are obtained by grinding the active ingredient with finely distributed solids, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Suspension concentrates may be water- or oil-based. They may be produced, for example, by wetgrinding by means of commercial bead mills and optional addition of surfactants as already listed above, for example, for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be produced, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants as already listed above, for example, for the other formulation types.

Granules can be produced either by spraying the active ingredient onto granular inert material capable of adsorption or by applying active ingredient concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium poly acrylate or else mineral oils. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules - if desired as a mixture with fertilizers.

Water-dispersible granules are produced generally by processes such as spray-drying, fluidized bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material. The agrochemical preparations generally contain 0.1 to 99 per cent by weight, especially 0.2% to 95% by weight, of active ingredients of types (A) and/or (B), the following concentrations being customary, depending on the type of formulation:

In wettable powders, the active ingredient concentration is, for example, about 10% to 95% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In the case of emulsifiable concentrates, the active ingredient concentration may be about 1% to 90% by weight, preferably 5 to 80 per cent by weight.

Formulations in the form of dusts usually contain 5% to 20% by weight of active ingredient; sprayable solutions contain about 0.05 to 80, preferably 2 to 50, per cent by weight (% by weight) of active ingredient.

In the case of granules such as dispersible granules, the active ingredient content depends partly on whether the active ingredient is in liquid or solid form and on which granulation auxiliaries and fillers are used. In general, the content in the water-dispersible granules is between 1% and 95% by weight, preferably between 10% and 80% by weight.

In addition, the active ingredient formulations mentioned optionally comprise the respectively customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, colorants and carriers, antifoams, evaporation inhibitors and pH- or viscosity-modifying agents.

For application, the formulations in the commercial form are diluted if appropriate in a customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Dust-type preparations, granules for soil application or broadcasting and sprayable solutions are not normally diluted further with other inert substances prior to application.

The active ingredients can be deployed onto the plants, plant parts, plant seeds or the area under cultivation (soil), preferably on the green plants and plant parts, and optionally additionally onto the soil.

One possible use is the joint application of the active ingredients in the form of tankmixes, where the optimally formulated concentrated formulations of the individual active ingredients together are mixed in a tank with water, and the spray liquor obtained is deployed.

A joint herbicidal formulation of the inventive combination of active ingredients (A) and (B) has the advantage that it can be applied more easily since the quantities of the components are already set at the correct ratio to one another. Moreover, the auxiliaries in the formulation can be adjusted optimally to one another, whereas a tank mix of different formulations may result in unwanted combinations of auxiliaries. A. General formulation examples a) A dusting product is obtained by mixing 10 parts by weight of an active ingredient (A) or (B) or an active ingredient mixture (A) + (B) (and optionally further active ingredient components such as component (C)) and/or salts thereof and 90 parts by weight of talc as inert substance, and comminuting in a beater mill. b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of an active ingredient/active ingredient mixture, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as wetting agent 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 ingredient/active ingredient 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 approximately 255 to 277°C) and grinding the mixture in a friction ball mill to a fineness of below 5 microns. d) An emulsifiable concentrate is obtained from 15 parts by weight of an active ingredient/active ingredient mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier. e) Water-dispersible granules are obtained by mixing

75 parts by weight of an active ingredient/active ingredient mixture,

10 parts by weight of calcium lignosulfonate,

5 parts by weight of sodium lauryl sulfate,

3 parts by weight of polyvinyl alcohol and

7 parts by weight of kaolin, grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spray application of water as a granulating liquid. f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill,

25 parts by weight of an active ingredient/active ingredient mixture,

5 parts by weight of sodium 2,2'-dinaphthylmethane-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, then grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a one-phase nozzle.

B. Biological examples: Flumioxazin + Aclonifen

The following data are the results of a greenhouse investigation in which the herbicide combination according to the present invention was tested against various monocotyledonous and dicotyledonous weeds after a pre-emergence application and an post emergence application (BBCH 10-12). The following weeds were selected for testing:

Table 1

For the trials seeds of the above-mentioned species were sown in 7 cm pots containing standard soil (14,7% sand, 19,9% clay, 65,4% silt and 1,8% organic matter) covered with 0,5 cm depth of sandy soil, lightly irrigated from above and used for the pre emergence trial. For the post emergence trial the pots were placed in a glasshouse (with conditions of 16 hour day and 8 hour night, 21 °C day and 12°C night and 60% relative humidity) and irrigated from above to allow the seeds to germinate and grow. Once they had reached the required growth stage BBCH 10-12 the propagated plants were used for the post emergence trial. The herbicide application was done with a track sprayer at a spray volume of 300 1 water/ha using a flat fan nozzle XR 8001 at a pressure of 1.8 bar. For the preparation of the application liquids the formulations shown in the table 2 were used. The methylated rape seed oil adjuvant Mero® was added to each application liquid with 1 1/ha. After the application and air drying the pots were placed back into the glasshouse and allowed to grow on. The pots were irrigated as required for good plant growth.

Table 2

Visual percent of weed control (2 replicates) was rated in intervals after application, indicated in the result tables as days after herbicide application (DAA) on a scale of 0-100. A rating of 0 is defined as no control and 100 as complete control.

On employment of the combinations of the invention, herbicidal effects on a harmful plant species that exceed the formal sum total of the effects of the herbicides present when applied alone were frequently observed. Alternatively, in some cases, it was possible to observe that a smaller application rate for the herbicide combination is required in order to achieve the same effect for a harmful plant species compared to the individual preparations. Such increases in action or increases in effectiveness or reductions in application rate are a strong indication of a synergistic effect.

When the observed efficacies already exceed the formal sum total of the values of the tests with individual applications, they also exceed the expected value according to Colby, which is calculated using the formula below and is likewise regarded as an indication of synergism (cf. S. R. Colby; in Weeds 15 (1967) pp. 20 to 22):

E^c = A+B - (A-B/100) where:

A = efficacy of the active ingredient (A) in % at an application rate of a [g a.i./ha] ;

B = efficacy of the active ingredient (B) in % at an application rate of b [g a.i./ha] ;

E^c = expected value of the effect of the combination (A)+(B) in % at the combined application rate a+b [g a.i./ha] .

The observed values (E^A) from the experiments, given suitable low dosages, show an effect of the combinations exceeding the expected values according to Colby (E^c) (A). The post emergence trial as well as the pre emergence trial results show, that the combination of flumioxazin and aclonifen at the above mentioned dose rates produces high efficacy, clearly higher than expected according to Colby, against the target weeds tested. This indicates clear synergism between flumioxazin and aclonifen.

Table 4: Post emergence trial: % Efficacy against various weeds

Table 5: Post emergence trial: % Efficacy against various weeds

Table 6: Pre emergence trial: % Efficacy against various weeds

Table 7: Pre emergence trial: % Efficacy against various weeds C. Biological examples: Flumioxazin + Aclonifen + Diflufenican

The following data are the results of a greenhouse investigation in which the herbicide combination according to the present invention was tested against various monocotyledonous and dicotyledonous weeds after an pre emergence application and an early-post emergence application (BBCH 10-11). The following weeds were selected for testing:

Table 8

For the trials seeds of the above mentioned species were sown in 7 cm pots containing standard soil (14,7% sand, 19,9% clay, 65,4% silt and 1,8% organic matter) covered with 0,5 cm depth of sandy soil, lightly irrigated from above and used for the pre emergence trial. For the early post emergence trial the pots were placed in a glasshouse (with conditions of 16 hour day and 8 hour night, 21 °C day and 12°C night and 60% relative humidity) and irrigated from above to allow the seeds to germinate and grow. Once they had reached the required growth stage BBCH 10-11 the propagated plants were used for the early post emergence trial. The herbicide application was done with a track sprayer at a spray volume of 300 1 water/ha using a flat fan nozzle XR 8001 at a pressure of 1.8 bar. After the application and air drying the pots were placed back into the glasshouse and allowed to grow on. The pots were irrigated as required for good plant growth. The treatments are shown in table below.

Table 9

Visual percent of weed control (2 replicates) was rated 20 days after herbicide applications (DAA) on a scale of 0-100. A rating of 0 is defined as no control and 100 as complete control. According to Colby synergistic effects of herbicidal active ingredients are indicated if the measured efficacy is higher than the expected one calculated according to his formula for 3 -way mixtures:

E = (A + B + C) - (AxB + AxC + BxC)/100 + (AxBxQ/10000

The early post emergence trial as well as the pre emergence trial result show, that the combination of aclonifen, diflufenikan and flumioxazin at the above mentioned dose rates produces high efficacy, clearly higher than expected according to Colby, against the target weeds tested. This indicates clear synergism between these three active ingredients.

Table 10: Early post emergence trial: % Efficacy against various weeds

Table 11: Pre emergence trial: % Efficacy against various weeds

Claims

Claims:

1. Composition comprising compounds (A) and (B) wherein

(A) represents flumioxazin, and

(B) represents aclonifen.

2. Composition according to claim 1, wherein (A) and (B) are provided in a weight ratio of 200: 1 to 1:200, preferably 100:1 to 1:100.

3. Composition according to claim 1 or 2, further comprising compound (C), wherein (C) represents diflufenican.

4. Composition according to claim 3, wherein (A) and (C) are provided in a weight ratio of 200: 1 to 1:200, preferably 100:1 to 1:100.

5. Composition according to any one of claims 1 to 4, additionally comprising one or more further constituents selected from the group consisting of further herbicides, water, formulation adjuvants, and safeners.

6. Composition according to any one of claims 1 to 5, further comprising at least one safener, preferably selected from mefenpyr-diethyl and cloquintocet-mexyl, further preferably mefenpyr- diethyl.

7. Composition according to any one of claims 1 to 6, wherein the composition is in the form of a concentrated formulation or a ready-to-use diluted spray application mixture (tank-mix).

8. Method of controlling weed plants in a cereal crop field, preferably a wheat or barley field, characterized in that a composition according to any of claims 1 to 7 is applied to the weed plants, plants, plant seeds, or to the area on which the weed plants are growing.

9. Method according to claim 8, wherein the compounds of the composition are applied jointly or separately by the pre-emergence method, the post-emergence method or by the pre- and postemergence method to the plants, plant parts, plant seeds or the area under cultivation.

10. Method according to claims 8 or 9, wherein flumioxazin is applied at an application rateof between 1 and 200 g ai/ha.

11. Method according to any one of of claims 8 to 10, wherein aclonifen is applied at an application rate of between 50 and 2500 g ai/ha.

12. Method according to any one of claims 8 to 10, wherein diflufenican is applied at an application rate of between 5 and 1000 g ai/ha.