EP2328415A2

EP2328415A2 - Herbicidal combination comprising dimethoxytriazinyl-substituted difluoromethane sulfonylanilides

Info

Publication number: EP2328415A2
Application number: EP09777757A
Authority: EP
Inventors: Erwin Hacker; Christian Waldraff; Christopher Hugh Rosinger; Chieko Ueno; Georg Bonfig-Picard; Stefan Schnatterer; Shinichi Shirakura
Original assignee: Bayer CropScience AG
Current assignee: Bayer CropScience AG
Priority date: 2008-08-14
Filing date: 2009-08-08
Publication date: 2011-06-08
Also published as: CO6341521A2; CN102186349A; KR20110042223A; AR073033A1; US20100075852A1; WO2010017927A2; JP5613161B2; KR101663097B1; CN103999864A; CN103999864B; WO2010017927A3; BRPI0917677A2; JP2011530554A; CN102186349B; WO2010017927A8; TW201022218A; DE102008037628A1

Abstract

The invention relates to a herbicidal combination containing components (A) and (B), (A) representing one or more compounds or salts thereof from the group described by general formula (I), wherein R1 represents halogen, preferably fluorine or chlorine, R2 represents hydrogen and R3 represents hydroxyl or R2 and R3 together with the carbon atom to which they are bound, represent a carbonyl group C=O and R4 represents hydrogen or methyl; and (B) represents one or more herbicides from the group comprising: (B1-1) benzofenap; (B1-2) pyrazolynate; (B1-3) pyrazoxyfen; (B1-4) pyroxasulfone; (B1-5) topramezone; (B1-6) pyrasulfotole; (B1-7) NC-310; (B2-1 ) pyraflufen-ethyl; (B2-2) fluazolate; (B3-1) isouron; (B3-2) isoxaben; (B3-3) isoxaflutole; (B4-1) imazamethabenz-methyl; (B4-2) imazamox; (B4-3) imazapic; (B4-4) imazapyr; (B4-5) imazaquin; (B4-6) imazethapyr; (B4-7) profluazol; (B5-1) methazole; (B5-2) oxadiargyl; (B5-3) oxadiazon; (B6-1) amicarbazone; (B6-2) carfentrazone-ethyl; (B6-3) sulfentrazone; (B6-4) bencarbazone; (B6-5) ipfencarbazone; (B7-1) amitrole; (B7-2) paclobutrazol; (B7-3) uniconazole; (B7-4) cafenstrole; (B8-1) fentrazamid; (B8-2) F-5231.

Description

Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides

description

The present invention is in the technical field of crop protection agents against unwanted plant growth, for example (eg) in Vorsaatverfahren (with or without incorporation), in the pre-emergence or postemergence in sown and / or planted crops such as wheat (hard and soft wheat ), Corn, soybean, sugarbeet, sugar cane, cotton, rice (planted or sown under 'upland' or 'paddy' conditions with indica and / or japonica species, and hybrids / mutants / GMOs), beans (such as bush bean and horse bean), flax, barley, oats, rye, triticale, rapeseed, potato, millet (sorghum), pasture grass, green / lawns, in orchards (plantation crops) or on non-cultivated areas (eg squares of residential and industrial plants, railway tracks ) can be used. In addition to the single application, sequence applications are also possible.

It relates to a herbicide combination comprising at least two herbicides and their use for controlling undesired plant growth, in particular a herbicide combination comprising Λ / - {2- [4,6-dimethoxy- (1, 3,5) -triazine-2 (- carbonyl or -hydroxy-methyl)] - 6-halo-phenyl} -difluoromethanesulfonamides or their N-methyl derivatives and / or their salts, also referred to below as "dimethoxytriazinyl-substituted difluoromethanesulfonylanilides", and herbicidal active compounds from the group of the azoles ,

It is known that cyclic-substituted sulfonamides have herbicidal properties (eg WO 93/09099 A2, WO 96/41799 A1). These include the phenyldifluoromethanesulfonamides, which are also referred to as Difluormethansulfonylanilide. The latter are, for example, phenyl derivatives which are monosubstituted or polysubstituted, inter alia with Dimethoxypyimidinyl (eg WO 00/006553 A1) or dimethoxytriazinyl and a further halogen substitution (eg WO 2005/096818 A1, WO 2007/031208 A2).

Specific compounds from the group of Λ / - {2- [4,6-dimethoxy- (1, 3,5) triazine-2 (- carbonyl or -hydroxy-methyl)] - 6-halo-phenyl} -difluoromethanesulfonamides, as in WO 2005/096818 A1, and their Λ / -methyl derivatives, as described in WO 2006/008159 A1 in connection with fungicides for the first time and in WO 2007/031208 A2 and JP 2007-213330 (unpublished) as herbicides, are described in their herbicidal properties but not completely satisfactory in all respects.

The herbicidal activity of dimethoxytriazinyl-substituted difluoromethanesulfonylanilides against harmful plants (weeds, grass weeds, cyperaceans, also collectively referred to as "weeds" below) is already at a high level, but is generally dependent on the

Application rate, the particular form of preparation, each to be controlled harmful plants or the Schadpflanzenspektrum, the climate and soil conditions, etc. from. Other criteria in this context are the duration of the action or the degradation rate of the herbicide, the general crop tolerance and speed of action (faster

Efficacy), the spectrum of activity and behavior towards secondary crops (replication problems) or the general application flexibility (control of weeds in their different growth stages). If necessary, changes in the susceptibility of harmful plants, which can occur with prolonged use of the herbicides or geographically limited (control of tolerant or resistant weed species) must also be taken into account. Losses of activity in individual plants can only be compensated to a limited extent by higher application rates of the herbicides, e.g. because it reduces the selectivity of the herbicides or does not improve the efficacy even at higher application rates.

Thus, there is often a need for specifically synergistic activity against particular weed species, a weed control with overall better selectivity, one generally lower active ingredient use for equally good control success and for a lower level of active ingredient input into the environment, for example to avoid "leaching" and "carry-over" effects. There is also a need for the development of "one shot" applications to avoid laborious multiple applications, as well as the development of rate of action control systems, in addition to a first, rapid weed control, and slow, residual control.

A possible solution to the above-mentioned problems may be the provision of herbicide combinations, that is, the mixture of several herbicides and / or other components from the group of agrochemical active ingredients of other types as well as in crop protection conventional additives and formulation auxiliaries, which contribute the desired additional properties. However, the combined use of several drugs often causes phenomena of chemical, physical or biological incompatibility, e.g. lack of stability of a common formulation, decomposition of an active substance or antagonism in the biological activity of the active ingredients. Therefore, potentially suitable combinations have to be selected and tested experimentally for their suitability, whereby negative as well as positive results can not be ruled out in advance.

Mixtures of non-Λ / -methyl derivatives of the abovementioned compounds are known in principle (for example WO 2007/079965 A2), but their effectiveness in mixtures with other herbicides is proven only with dimethoxypyimidinyl-substituted phenyl derivatives in individual cases. In addition, there are also mixtures of selected Λ / -methyl derivatives of the above-mentioned compounds with some combination partners (PCT / EP2008 / 000870, unpublished).

The object of the present invention was to provide the prior art with alternative or improved pesticides. Surprisingly, it has now been found that this object can be achieved by herbicide combinations of dimethoxytriazinyl-substituted difluoromethanesulfonylanilides in combination with structurally different herbicides from the group of the azoles, which interact in a particularly favorable manner, for example when they are sown to combat unwanted plant growth / or planted crops such as wheat (hard and soft wheat), corn, soybean, sugarbeet, sugar cane, cotton, rice (planted or sown under 'Upland ¹ or' Paddy ¹ conditions with Indica and / or Japonica species and hybrids / Mutants / GMOs), beans (such as common bean and horse bean), flax, barley, oats, rye, triticale, rapeseed, potato, millet (sorghum), pasture, green / grassy areas, orchards (plantation crops) or non- Cultivated areas (eg squares of residential and industrial plants, railway tracks), especially in rice crops (planted or sown under 'Upland ¹ or 'Paddy ¹ ' conditions with Indica and / or Japonica species as well as hybrids / mutants / GMOs).

Compounds from the group of the azoles are already known as herbicidal active substances for the control of undesired plant growth; see for example JP 57072903, GB 1463473, US 4230481, WO 2002062770, EP 958291, WO 2001074785, GB 2122188, WO 2006103003, EP 361114, WO 09206962, DE 2436179, US 4636243, EP 527036, US 4188487, EP 254951, EP 41624 EP 41623, US 4798619, DE 2227012, GB 1110500, DE 3839206, WO 09002120, WO 08703782, DE 19500439, US 2670282, US 1595697, US 4203995, US 5147445, EP 612735, WO 08703873 and those cited in the aforementioned publications Literature.

The present invention thus relates to a herbicide combination comprising components (A) and (B), where (A) one or more compounds or salts thereof from the group described by the general formula (I):

wherein

R ^{1 is} halogen, preferably fluorine or chlorine, R ^{2 is} hydrogen and R ^{3 is} hydroxyl or

R ² and R ^{3 taken} together with the carbon atom to which they are attached represent a carbonyl group C = O and R ^{4 is} hydrogen or methyl;

and

(B) means one or more herbicides from the group of the azoles consisting of:

the subgroup of pyrazoles (subgroup 1) consisting of: (B1-1) benzofenap (PM # 72), e.g. 2 - [[4- (2,4-dichloro-3-methylbenzoyl) -1,3-dimethyl-1H-pyrazol-5-yl] oxy] -1- (4-methylphenyl) ethanone

(Application rate: 1 - 5000 g AS / ha, preferably 3 - 4000 g AS / ha;

Weight ratio A: B = 1: 5000 - 500: 1, preferably 1: 800 -

70: 1); (B1-2) pyrazolynate (PM # 712), syn. pyrazolates, e.g. (2,4-dichlorophenyl) [1,3-dimethyl-5 - [[(4-methylphenyl) sulfonyl] oxy] -1H-pyrazol-4-yl] methanone

(Application rate: 1 - 5000 g AS / ha, preferably 3 - 4000 g AS / ha;

Weight ratio A: B = 1: 5000 - 500: 1, preferably 1: 800 -

70: 1); (B1 -3) pyrazoxyfen (PM # 715), e.g. 2 - [[4- (2,4-dichlorobenzoyl) -1,3-dimethyl

1 / - / - pyrazol-5-yl] oxy] -1-phenylethanone (application rate: 1 - 5000 g

AS / ha, preferably 3 - 4000 g AS / ha; Weight ratio A: B = 1: 5000-500: 1, preferably 1: 800-70: 1); (B1-4) Pyroxasulfones (CPCN) ₁ syn. KIH 485, eg 3 - [[[5- (difluoromethoxy) -1-methyl-3- (trifluoromethyl) -1H-pyrazol-4-yl] methyl] sulfonyl] -4,5-dihydro-5,5-dimethylisoxazole ( Application rate: 1 to 5000 g AS / ha, preferably 3 to 4000 g AS / ha, weight ratio A: B = 1: 5000

500: 1, preferably 1: 800 - 70: 1);

(B1-5) Toprame zone (PM # 831), e.g. [3- (4,5-dihydro-3-isoxazolyl) -2-methyl-4- (methylsulfonyl) phenyl] (5-hydroxy-1-methyl-1H-pyrazol-4-yl) methanone (application rate: 1 - 5000 g AS / ha, preferably 3 - 4000 g AS / ha; weight ratio A: B = 1: 5000-500: 1, preferably 1: 800-70: 1);

(B1-6) pyrasulfotole (CPCN), e.g. (5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl) [2- (methylsulfonyl) -4- (trifluoromethyl) phenyl] methanone (application rate: 1-5000 g AS / ha, preferably 3-4000 g AS / ha; weight ratio A: B = 1: 5000 - 500: 1, preferably 1: 800 -

70: 1);

(B1-7) NC-310 (described in: GB2122188; Inf. Of Nitokuno, June 3rd, 1985 "Major Competitive Compounds Under Development in Japan", H-23.), E.g. 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazol; (2,4-dichlorophenyl) [1-methyl-5- (phenylmethoxy) -1H-pyrazole-4-yl] -methane one; Chemical Abstract Service Registry Number [CAS RN 89275-30-9] (application rate: 1 - 5000 g AS / ha, preferably 3 - 4000 g AS / ha; weight ratio A: B = 1: 5000 - 500: 1, preferably 1: 800-70: 1);

the subset of phenylpyrazoles (subgroup 2) consisting of: (B2-1) pyraflufen-ethyl (PM # 711), syn. ET 751, e.g. ethyl 2-chloro-5- [4-chloro-5- (difluoromethoxy) -1-methyl-1H-pyrazol-3-yl] -4-fluorophenoxyacetate, which also comprises its acid (pyraflufen) and other esters and salts (derivatives ) (Application rate: 0.1 - 600 g

AS / ha, preferably 1-500 g AS / ha; Weight ratio A: B = 1: 600 - 5000: 1, preferably 1: 100 - 200: 1); (B2-2) Fluazolates (PM # 1202), eg 1-methylethyl 5- [4-bromo-1-methyl-5- (trifluoromethyl) -1 / - / - pyrazol-3-yl] -2-chloro-4 -fluorobenzoates (application rate: 1-5000 g AS / ha, preferably 3-4000 g AS / ha; weight ratio A: B = 1: 5000-500: 1, preferably 1: 800-70: 1);

subgroup of isoxazoles (subgroup 3), consisting of:

(B3-1) isourone (PM # 492), e.g. / V- [5- (1,1-dimethylethyl) -3-isoxazolyl] -A /, / V-dimethylurea (application rate: 10-5000 g AS / ha, preferably 30-4000 g AS / ha; weight ratio A: B = 1: 5000-50: 1, preferably 1: 800-7: 1);

(B3-2) isoxaben (PM # 493), e.g. / V- [3- (1-ethyl-1-methylpropyl) -5-isoxazolyl] -2,6-dimethoxybenzamide (application rate: 1-500 g AS / ha, preferably 2-400 g AS / ha; weight ratio A: B = 1: 500-500: 1, preferably 1: 80-100: 1);

(B3-3) Isoxaflutole (PM # 495), e.g. (5-cyclopropyl-4-isoxazolyl) [2- (methylsulfonyl) -4- (trifluoromethyl) phenyl] methanone (application rate: 1-800 g AS / ha, preferably 2-600 g AS / ha; weight ratio A: B = 1 : 800-500: 1, preferably 1: 120-100: 1);

the subgroup of imidazolinones (subgroup 4) consisting of: (B4-1) imazamethabenz-methyl (PM # 463), e.g. reaction product comprising methyl (±) -6- (4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) -A77-toluate and methyl (±) -2- (4-isopropyl-4-) methyl-5-oxo-2-imidazolin-2-yl) -p-toluate, including its acid (imazamethabenz, mixture of acid stereoisomers) and other esters and salts (derivatives) (application rate: 1 - 1000 g AS / ha, preferably 2 - 800 g AS / ha; weight ratio A: B = 1: 1000-500: 1, preferably 1: 160-100: 1);

(B4-2) Imazamox (PM # 464), eg (±) -2- [4,5-dihydro-4-methyl-4- (1-methylethyl) -5-oxo-1 / - / - imidazole-2 -yl] -5- (methoxymethyl) -3- pyridinecarboxylic acid, comprising its racemate and isomers including their salts, such as the ammonium salt, and esters (derivatives) (application rate: 1-1000 g AS / ha, preferably 2-800 g AS / ha; weight ratio A: B = 1: 1000-500: 1, preferably 1: 160-100: 1);

(B4-3) Imazapic (PM # 465), syn. AC 263222, e.g. (±) -2- [4,5-dihydro-4-methyl-4- (1-methylethyl) -5-oxo-1H-imidazol-2-yl] -5-methyl-3-pyridinecarboxylic acid, comprising Racemate and also isomers including their salts, such as the ammonium salt, and esters (derivatives) (application rate: 1-1000 g AS / ha, preferably 2-800 g AS / ha; weight ratio A: B = 1: 1000-500: 1, preferably 1: 160-100: 1) ; (B4-4) imazapyr (PM # 466), e.g. (±) -2- [4,5-dihydro-4-methyl-4- (1-methyl-ethyl) -5-oxo-1H-imidazol-2-yl] -3-pyridinecarboxylic acid, including its racemate and isomers including their

Salts, e.g. the isopropylammonium salt, and esters (derivatives) (application rate: 1-1000 g AS / ha, preferably 2-800 g AS / ha; weight ratio A: B = 1: 1000-500: 1, preferably 1: 160-100: 1) ; (B4-5) imazaquin (PM # 467), e.g. (±) -2- [4,5-dihydro-4-methyl-4- (1-methylethyl) -5-oxo-1 / - / - imidazol-2-yl] -3-quinolinecarboxylic acid comprising its racemate and also isomers including their salts, such as the ammonium and sodium salt, and esters, e.g. the methyl ester, (derivatives) (application rate: 1 - 1000 g AS / ha, preferably 2 - 800 g AS / ha; weight ratio A: B = 1: 1000 -

500: 1, preferably 1: 160-100: 1); (B4-6) imazethapyr (PM # 468), e.g. (±) -2- [4,5-dihydro-4-methyl-4- (1-methylethyl-δ-oxo-IH-imidazol-1-yl-yl-ethyl-S-pyridinecarboxylic acid comprising its racemate and also isomers including their salts, such as the ammonium salt, and esters (derivatives)

(Application rate: 1 - 1000 g AS / ha, preferably 2 - 800 g AS / ha; weight ratio A: B = 1: 1000 - 500: 1, preferably 1: 160 - 100: 1);

(B4-7) Profluazole (PM # 1399), e.g. 1-chloro-Λ / - [2-chloro-4-fluoro-5 - [(6S, 7aR) -6-fluoro-tetrahydro-1,3-dioxo-1H-pyrrolo [1,2-c] imidazole-2 ( 3H) - yl] phenyl] methanesulfonamide (application rate: 1 - 1000 g AS / ha, preferably 2 - 800 g AS / ha; weight ratio A: B = 1: 1000 -

500: 1, preferably 1: 160-100: 1);

subgroup of oxadiazolones (group 5) consisting of: (B5-1) methazoles (PM # 1310), e.g. 2- (3,4-dichlorophenyl) -4-methyl-1,2,4-oxadiazolidine-3,5-diones (application rate: 10-5000 g AS / ha, preferably 30-4000 g AS / ha; B = 1: 5000-50: 1, preferably 1: 800-7: 1);

(B5-2) Oxadiargyl (PM # 617), e.g. 3- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5- (1, 1-dimethylethyl) -1, 3,4-oxadiazol-2 (3 / - /) - one (application rate: 2 , 5 - 1500 g AS / ha, preferably 5 - 1000 g AS / ha; weight ratio A:

B = 1: 1500-200: 1, preferably 1: 200-40: 1); (B5-3) Oxadiazone (PM # 618), e.g. 3- [2,4-dichloro-5- (1-methylethoxy) phenyl] - 5- (1,1-dimethylethyl) -1,3,4-oxadiazol-2 (3 / - /) -one (application rate: 5 - 5000 g AS / ha, preferably 10 - 4000 g AS / ha; weight ratio A: B = 1: 5000 - 100: 1, preferably 1: 800 - 20: 1);

subgroup of triazolinones (subgroup 6) consisting of: (B6-1) amicarbazone (PM # 21), e.g. 4-Amino-Λ / - (1, 1-dimethylethyl) -4,5-dihydro-3- (1-methylethyl) -5-oxo-1 H-1, 2,4-triazole-i-carboxamides (application rate of 1 1000 g AS / ha, preferably 5 to 800 g AS / ha;

Weight ratio A: B = 1: 1000-500: 1, preferably 1: 160-40: 1); (B6-2) carfentrazone-ethyl (PM # 123), e.g. ethyl α, 2-dichloro-5- [4-

(Difluoromethyl) -4,5-dihydro-3-methyl-5-oxo-1-HA, 2,4-triazol-1-yl] -4-fluorobenzenepropanoate, including its acid carfentrazone (eg α, 2-dichloro-5 [4- (difluoromethyl) -4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl] -4-fluorobenzenepropanoic acid) and further esters (derivatives) (application rate: 0.1-500 g AS / ha, preferably 1-300 g AS / ha; weight ratio A: B = 1: 500-5000: 1, preferably 1: 30-200: 1) ;

(B6-3) Sulfene Trazone (PM # 769), e.g. Λ / - [2,4-dichloro-5- [4- (difluoromethyl) -4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl] -phenyl] methanesulfonamides (amount required: 1-5000 g AS / ha, preferably 3-4000 g AS / ha; weight ratio A: B = 1: 5000-500: 1, preferably 1: 800-70: 1); (B6-4) Bencarbazone (CPCN), e.g. 4- [4,5-dihydro-4-methyl-5-oxo-3- (trifluoromethyl) -i H -1,2,4-triazol-1-yl] -2 - [(ethylsulfonyl) amino] -5- fluorobenzenecarbothioamide (application rate: 1 - 5000 g AS / ha, preferably 3 - 4000 g AS / ha; weight ratio A: B = 1: 5000-500: 1, preferably 1: 800-70: 1); (B6-5) Ippocarbazone (described in: WO98 / 38176; AG CHEM NEW COMPOUND REVIEW, Vol. 18, 2000; Agricultural Chemical News

258 (2001), 5), syn. HOK-201, CHK-201, e.g. 1- (2,4-dichlorophenyl) -N- (2,4-difluorophenyl) -N- (1-methylethyl) -5-oxo-1,5-dihydro-4H-1,2,4-triazole-4- carboxamides; Chemical Abstract Service Registry Number [CAS RN 212201-70-2] (application rate: 1 - 5000 g AS / ha, preferably 3 - 4000 g AS / ha; weight ratio A: B = 1: 5000 -

500: 1, preferably 1: 800 - 70: 1);

subgroup of triazoles (subgroup 7) consisting of: (B7-1) amitrole (PM # 26), e.g. 1H-1, 2,4-triazole-3-amine (application rate: 1-5000 g AS / ha, preferably 3-4000 g AS / ha;

B = 1: 5000-500: 1, preferably 1: 800-70: 1);

(B7-2) paclobutrazole (PM # 630), eg (R *, ft * M ±) -β - [(4-chlorophenyl) methyl] -α- (1, 1-dimethylethyl) -1H-1, 2, 4-triazole-1-ethanol; Chemical Abstract Service Registry Number [CAS RN 76738-62-0], comprising its racemate and isomers (application rate: 1-5000 g AS / ha, preferably 3-4000 g AS / ha; weight ratio A: B = 1: 5000-500 : 1, preferably 1: 800-70: 1); (B7-3) Uniconazole (PM # 867), eg (E) - (±) -β - [(4-chlorophenyl) methylene] -α- (1, 1-dimethylethyl) -1H-1, 2,4- triazole-i-ethanol, comprising its racemate and isomers of (E) - (S) - (+) - isomer, E) - (R) - (-) - isomer, in particular uniconazole P ((S) -isomer) ( Application rate: 1 - 5000 g AS / ha, preferably 3 - 4000 g AS / ha; weight ratio A: B = 1

: 5000-500: 1, preferably 1: 800-70: 1);

(B7-4) Cafenstrole (PM # 112), syn. CH 900, e.g. Λ /, Λ / -diethyl-3 - [(2,4,6-trimethylphenyl) sulfonyl] -1H-1, 2,4-triazole-1-carboxamide (application rate: 3 - 3000 g AS / ha, preferably 5 - 1500 g AS / ha; weight ratio A: B = 1: 3000 - 170: 1, preferably 1: 500 -

40: 1);

the subgroup of tetrazolinones (subgroup 8), consisting of: (B8-1) Fentrazamide (PM # 359), syn. NBA 061, e.g. 4- (2-chlorophenyl) -Λ / -cyclohexyl-Λ / -ethyl-4,5-dihydro-5-oxo-1 / - / - tetrazoles-1-carboxamides

(Application rate: 5 - 3000 g AS / ha, preferably 10 - 2000 g AS / ha; weight ratio A: B = 1: 3000 - 100: 1, preferably 1: 400 - 20: 1);

(B8-2) F-5231 (described in: WO8703873, Pestic., 30 (1990), 259-274), e.g. N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl] -phenyl] -ethanesulfonamide; Chemical Abstract Service Registry Number [CAS RN 112190-78-0] (application rate: 1 - 5000 g AS / ha, preferably 3 - 4000 g AS / ha; weight ratio A: B = 1: 5000 - 500: 1, preferably 1: 800-70: 1);

excluding the following combinations described in PCT / EP2008 / 000870 (unpublished):

Compounds of the general formula (I) where R ^{1 is} fluorine, R ² and R ^{3 are} carbonyl group C = O, R ^{4 is} methyl, and the compounds B1-1 (benzofenap), B8-1 (fentrazamide). The compounds mentioned above in Group B are designated either by the "Common name" according to the International Organization for Standardization (ISO) or by the chemical name or by a code number (development code); as known, for example, from the following sources "The Pesticide Manual", 14th Edition 2006/2007 or "The e-Pesticide Manual", Version 4.0 (2006-07), each issued by the British Crop Protection Council (abbreviation: "PM #. "with the respective serial number /" sequential entry number "), and literature cited there, from" The Compendium of Pesticide Common Names "(abbreviation:" CPCN "; Internet URL: http://www.alanwood.net/pesticides /) and / or other sources. By using the abovementioned designations, for example in the short form of the "common name", all use forms (derivatives) such as acids, salts, esters and isomers such as stereoisomers and optical isomers are always included, unless already specifically defined. The commercial applications of the herbicides listed in Group B are preferred. The abbreviation "AS / ha" above means "active substance per hectare" and is based on 100% active ingredient.

Preferred as component (A) are the following compounds (A-1) to (A-8) of the formulas (A1), (A2), (A3), (A4), (A5), (A6), (A7) and (A8) or salts thereof:

As component (A), particularly preferred are the compounds (A-1), (A-2) and (A-3).

Compounds preferred as component (B) are: (B1-1) benzofenap, (B1-4) pyroxasulfones, (B1-5) toprame zone, (B1-6) pyrasulfotols, (B1-7) NC-310, (B3-2 ) Isoxaben, (B3-3) isoxaflutole, (B4-1) imazamethabenz-methyl, (B4-2) imazamox, (B4-3) imazapic, (B4-4) imazapyr, (B4-5) imazaquin, (B4-) 6) imazethapyr, (B5-2) oxadiargyl, (B5-3) oxadiazone, (B6-1) amicarbazone, (B6-2) carfentrazone-ethyl, (B6-3) sulfentrazone, (B6-5) isophorcarbazone, (B7 -1) Amitrole, (B7-2) Paclobutrazole, (B7-3) Uniconazole, (B7-4) Cafenstrole, (B8-1) Fentrazamide; particularly preferred (B1-1) benzofenap, (B1-4) pyroxasulfone, (B1-5) toprame zone, (B1-6) pyrasulfotole, (B3-3) isoxaflutole, (B4-2) imazamox, (B5-2) oxadiargyl , (B5-3) oxadiazone, (B6-1) amicarbazone, (B6-2) carfentrazone-ethyl, (B6-5) -propanecarbazone, (B7-4) cafenstrole, (B8-1) -fentrazamide.

The herbicidal combinations of the invention may contain additional additional components: e.g. agrochemical active compounds of another type and / or customary in plant protection additives and / or formulation auxiliaries, or used together with these. In the following, the use of the term "herbicide combination (s)" or "combination (s)" also includes the "herbicidal agents" thus produced.

The compounds of formula (I) can form salts. Salt formation can be effected by the action of a base on those compounds of the formula (I) which carry an acidic hydrogen atom. Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine and ammonium, Alkali or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate, alkali or alkaline earth alkylates, in particular sodium or potassium methoxide, ethylate, n-propylate, i-propylate, n-butoxide or t-butylate. These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts Examples of cations of the formula [NRR ^' R ^' R ^'' ] ⁺ , where R 1 to R ^''' each independently of one another are an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl. The compounds of the formula (I) can also be prepared by addition of a suitable inorganic or organic acid, such as, for example, mineral acids, such as, for example, HCl, HBr, H ₂ SO ₄ , H, and C 1 -C ₄ -trialkylsulphonium and (C 1 -C ₄ ) -trialkylsulfoxonium salts ₃ PO ₄ or

HNO ₃ , or organic acids, for example carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids, such as p-toluenesulfonic acid, to a basic group, such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino To form salts. These salts then contain the conjugate base of the acid as an anion.

In the following, for the term "component (s)", the terms "herbicide (s)", "single herbicide (s)", "compound (s)" or "active ingredient (s)" are used interchangeably in context.

In a preferred embodiment, the herbicidal combinations according to the invention contain the herbicides (A) and (B) in an effective content and / or have synergistic effects. The synergistic effects can be observed, for example, when the herbicides (A) and (B) are applied together, for example as a co-formulation or as a tank mixture, but they can also be detected in the case of staggered application (split application, splitting). It is also possible to use the herbicides or the herbicide combinations in multiple portions (sequence application), eg after pre-emergence applications, followed by post-emergence applications or early post-emergence applications, followed by mid-late post-emergence applications. Preference is given to the joint or the timely application of the herbicides (A) and (B) of the respective combination, particularly preferably the joint application.

The synergistic effects allow a reduction in the application rates of the individual herbicides, a higher and / or longer potency at the same rate, the control of previously unrecognized species (gaps), the control of species that have tolerances or resistance to single or multiple herbicides, an expansion the period of application and / or a reduction in the number of individual applications required and - as a result for the user - economically and ecologically more advantageous weed control systems.

For example, the combinations of herbicides (A) + (B) according to the invention make possible synergistic increases in activity that go far and unexpectedly beyond the effects achieved with the individual herbicides (A) and (B).

Said formula (I) comprises all stereoisomers and mixtures thereof, in particular racemic mixtures, and - as far as enantiomers are possible - the respective biologically active enantiomers. This also applies to possible rotamers of the formula (I).

The herbicides of group (A) mainly inhibit the enzyme acetolactate synthase (ALS) and thus protein biosynthesis in plants. The application rate of the herbicides (A) can vary within a wide range, for example between 0.1 g and 1000 g AS / ha (AS / ha in the following refers to "active substance per hectare" = based on 100% active ingredient) with application rates of 0.1 g to 1000 g AS / ha of the herbicides (A), preferably of the compounds (A-1) to (A- 8), in the pre-seed, pre-planting and pre- and post-emergence a relative combats a wide range of harmful plants, for example on annual and perennial, monocotyledonous or dicotyledonous weeds, grass weeds, cyperaceans and on unwanted crops. In the combinations according to the invention, the application rates are generally lower, for example in the range of 0.1 g to 500 g AS / ha, preferably 0.5 g to 200 g AS / ha, more preferably 1 g to 150 g AS / ha.

The herbicides of group (B) influence, for example, the p-hydroxyphenyl pyruvate dioxygenase, the phytoene desaturase, the porphyrinogen oxidase, the cellulose biosynthesis, the acetohydroxyacid synthase, the

Photosystem II, lycopene cyclase, gibberellin biosynthesis, cell division and the synthesis of long-chain fatty acids are suitable for pre-emergence as well as post-emergence applications. The application rate of the herbicides (B) can vary within a wide range, for example between 0.1 g and 5000 g AS / ha (AS / ha in the following means "active substance per hectare" = based on 100% active ingredient) at application rates of 1 g to 4000 g AS / ha of the herbicides (B), preferably of the compounds (B1-1), (B1-4), (B1-5), (B1-6), (B1-7), (B3-2), (B3-3), (B4-1), (B4-2), (B4-3), (B4-4), (B4-5), (B4-6), (B5 -2), B5-3, B6-1, B6-2, B6-3, B6-5, B7-1, B7-2, B7-3 ), (B7-4) and (B8-1), a relatively broad spectrum of harmful plants is fought in pre- and post-emergence, for example, on annual and perennial, monocotyledonous or dicotyledonous weeds, grass weeds, cyperaceans and undesirable crops Combinations of the invention are generally lower, for example in the range of 0.1 g to 5000 g AS / ha, preferably from 1 g to 4000 g AS / ha, more preferably 2 g to 3000 g AS / ha.

Preference is given to herbicide combinations of one or more herbicides (A) with one or more herbicides (B). Further preferred are combinations of herbicides (A) with one or more herbicides (B). In this case, those combinations according to the invention, the one or more further, from

Herbicides (A) and (B) contain various agrochemical active substances, which also have the function of a selective herbicide. For combinations with three or more active ingredients, the preferred conditions explained below in particular for two-member combinations according to the invention also apply primarily insofar as they contain the two-membered combinations according to the invention.

Areas for suitable proportions of the compounds (A) and (B) are given by e.g. from the stated application rates for the individual substances. In the combinations according to the invention, the application rates can be reduced as a rule. Preferred mixing ratios of the combined herbicides (A): (B) in the combinations according to the invention are characterized by the following weight ratios:

The weight ratio (A) :( B) of the components (A) and (B) is generally in the range of 1: 5000 to 5000: 1, preferably 1: 3000 to 500: 1, especially 1: 1500 to 200: 1.

Of particular interest is the use of herbicide combinations containing the following compounds (A) + (B):

(A-1) + (B1 -1), (A-1) + (B1 -2), (A-1) + (B1 -3), (A-1) + (B1 -4), (A -1) + (B1 -5), (A-1) + (B1-6), (A-1) + (B1-7), (A-1) + (B2-1), (A-1 ) + (B2-2), (A-1) + (B3-1), (A-1) + (B3-2), (A-1) + (B3-3), (A-1) + (B4-1), (A-1) + (B4-2), (A-1) + (B4-3), (A-1) + (B4-4), (A-1) + (B4 -5), (A-1) + (B4-6), (A-1) + (B4-7), (A-1) + (B5-1), (A-1) + (B5-2 ), (A-1) + (B5-3), (A-1) + (B6-1), (A-1) + (B6-2), (A-1) + (B6-3), (A-1) + (B6-4), (A-1) + (B6-5), (A-1) + (B7-1), (A-1) + (B7-2), (A -1) + (B7-3), (A-1) + (B7-4), (A-1) + (B8-1), (A-1) + (B8-2);

(A-2) + (B1-1), (A-2) + (B1-2), (A-2) + (B1-3), (A-2) + (B1-4), (A -2) + (B1-5), (A-2) + (B1-6), (A-2) + (B1-7), (A-2) + (B2-1), (A-2 ) + (B2-2), (A-2) + (B3-1), (A-2) + (B3-2), (A-2) + (B3-3), (A-2) + (B4-1), (A-2) + (B4-2), (A-2) + (B4-3), (A-2) + (B4-4), (A-2) + (B4 -5), (A-2) + (B4-6), (A-2) + (B4-7), (A-2) + (B5-1), (A-2) + (B5-2 ), (A-2) + (B5-3), (A-2) + (B6-1), (A-2) + (B6-2), (A-2) + (B6-3), (A-2) + (B6-4), (A-2) + (B6-5), (A-2) + (B7-1), (A-2) + (B7-2), (A -2) + (B7-3), (A-2) + (B7-4), (A-2) + (B8-1), (A-2) + (B8-2);

(A-3) + (B1-1), (A-3) + (B1-2), (A-3) + (B1-3), (A-3) + (B1-4), (A -3) + (B1-5), (A-3) + (B1-6), (A-3) + (B1-7), (A-3) + (B2-1), (A-3 ) + (B2-2), (A-3) + (B3-1),

(A-3) + (B3-2), (A-3) + (B3-3), (A-3) + (B4-1), (A-3) + (B4-2), (A -3) + (B4-3),

(A-3) + (B4-4), (A-3) + (B4-5), (A-3) + (B4-6), (A-3) + (B4-7), (A -3) + (B5-1),

(A-3) + (B5-2), (A-3) + (B5-3), (A-3) + (B6-1), (A-3) + (B6-2), (A -3) + (B6-3),

(A-3) + (B6-4), (A-3) + (B6-5), (A-3) + (B7-1), (A-3) + (B7-2), (A -3) + (B7-3), (A-3) + (B7-4), (A-3) + (B8-1), (A-3) + (B8-2);

(A-4) + (B1-1), (A-4) + (B1-2), (A-4) + (B1-3), (A-4) + (B1-4), (A -4) + (B1-5), (A-4) + (B1-6), (A-4) + (B1-7), (A-4) + (B2-1), (A-4 ) + (B2-2), (A-4) + (B3-1), (A-4) + (B3-2), (A-4) + (B3-3), (A-4) + (B4-1), (A-4) + (B4-2), (A-4) + (B4-3), (A-4) + (B4-4), (A-4) + (B4 -5), (A-4) + (B4-6), (A-4) + (B4-7), (A-4) + (B5-1), (A-4) + (B5-2 ), (A-4) + (B5-3), (A-4) + (B6-1), (A-4) + (B6-2), (A-4) + (B6-3), (A-4) + (B6-4), (A-4) + (B6-5), (A-4) + (B7-1), (A-4) + (B7-2), (A -4) + (B7-3), (A-4) + (B7-4), (A-4) + (B8-1), (A-4) + (B8-2);

(A-5) + (B1-1), (A-5) + (B1-2), (A-5) + (B1-3), (A-5) + (B1-4), (A -5) + (B1-5), (A-5) + (B1-6), (A-5) + (B1-7), (A-5) + (B2-1), (A-5 ) + (B2-2), (A-5) + (B3-1), (A-5) + (B3-2), (A-5) + (B3-3), (A-5) + (B4-1), (A-5) + (B4-2), (A-5) + (B4-3), (A-5) + (B4-4), (A-5) + (B4 -5), (A-5) + (B4-6), (A-5) + (B4-7), (A-5) + (B5-1), (A-5) + (B5-2 ), (A-5) + (B5-3), (A-5) + (B6-1), (A-5) + (B6-2), (A-5) + (B6-3), (A-5) + (B6-4), (A-5) + (B6-5), (A-5) + (B7-1), (A-5) + (B7-2), (A -5) + (B7-3), (A-5) + (B7-4), (A-5) + (B8-1), (A-5) + (B8-2);

(A-6) + (B1-1), (A-6) + (B1-2), (A-6) + (B1-3), (A-6) + (B1-4), (A -6) + (B1-5), (A-6) + (B1-6), (A-6) + (B1-7), (A-6) + (B2-1), (A-6 ) + (B2-2), (A-6) + (B3-1), (A-6) + (B3-2), (A-6) + (B3-3), (A-6) + (B4-1), (A-6) + (B4-2), (A-6) + (B4-3), (A-6) + (B4-4), (A-6) + (B4 -5), (A-6) + (B4-6), (A-6) + (B4-7), (A-6) + (B5-1), (A-6) + (B5-2 ), (A-6) + (B5-3), (A-6) + (B6-1), (A-6) + (B6-2), (A-6) + (B6-3), (A-6) + (B6-4), (A-6) + (B6-5), (A-6) + (B7-1), (A-6) + (B7-2), (A -6) + (B7-3), (A-6) + (B7-4), (A-6) + (B8-1), (A-6) + (B8-2);

(A-7) + (B1-1), (A-7) + (B1-2), (A-7) + (B1-3), (A-7) + (B1-4), (A -7) + (B1-5), (A-7) + (B1 -6), (A-7) + (B1 -7), (A-7) + (B2-1), (A-7 ) + (B2-2), (A-7) + (B3-1),

(A-7) + (B3-2), (A-7) + (B3-3), (A-7) + (B4-1), (A-7) + (B4-2), (A -7) + (B4-3),

(A-7) + (B4-4), (A-7) + (B4-5), (A-7) + (B4-6), (A-7) + (B4-7), (A -7) + (B5-1),

(A-7) + (B5-2), (A-7) + (B5-3), (A-7) + (B6-1), (A-7) + (B6-2), (A -7) + (B6-3),

(A-7) + (B6-4), (A-7) + (B6-5), (A-7) + (B7-1), (A-7) + (B7-2), (A -7) + (B7-3), (A-7) + (B7-4), (A-7) + (B8-1), (A-7) + (B8-2);

(A-8) + (B1-1), (A-8) + (B1-2), (A-8) + (B1-3), (A-8) + (B1-4), (A -8) + (B1-5), (A-8) + (B1-6), (A-8) + (B1-7), (A-8) + (B2-1), (A-8 ) + (B2-2), (A-8) + (B3-1), (A-8) + (B3-2), (A-8) + (B3-3), (A-8) + (B4-1), (A-8) + (B4-2), (A-8) + (B4-3), (A-8) + (B4-4), (A-8) + (B4 -5), (A-8) + (B4-6), (A-8) + (B4-7), (A-8) + (B5-1), (A-8) + (B5-2 ), (A-8) + (B5-3), (A-8) + (B6-1), (A-8) + (B6-2), (A-8) + (B6-3), (A-8) + (B6-4), (A-8) + (B6-5), (A-8) + (B7-1), (A-8) + (B7-2), (A -8) + (B7-3), (A-8) + (B7-4), (A-8) + (B8-1), (A-8) + (B8-2).

Furthermore, herbicide combinations according to the invention as additional additional components, various agrochemical active ingredients, for example from the group of safeners, fungicides, insecticides, acaricides, nematicides, bird repellants, soil conditioners, plant nutrients (fertilizers), and structurally from the herbicides (A) and (B) contain different herbicides and plant growth regulators or from the group of customary in plant protection additives and formulation auxiliaries.

Thus, as further herbicides, for example, the herbicides which differ structurally from the herbicides (A) and (B) are suitable, preferably herbicidal active compounds which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate- 3-phosphate synthase, Glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 13th edition 2003 or 14th Edition 2006/2007, or in the corresponding "The e-Pesticide Manual", Version 4.0 (2006-07), each issued by the British Crop Protection Council, and cited therein. Lists of common names are also available on The Internet in The Compendium of Pesticide Common Names. The herbicides are hereby designated either by the "Common Name" according to the International Organization for Standardization (ISO) or by the chemical name or by the code number, and always include all forms of use, such as acids, salts, esters and isomers, such as stereoisomers and optical isomers. Examples include one and in part also several forms of use: acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amidochlor, amidosulfuron, aminocyclopyrachlor, aminopyralid, Ammonium sulfamate, ancymidol, anilofos, asulam, atrazines, azafenidine, azimsulfuron, aziprotryn, BAH-043, BAS-140H, BAS-693H, BAS-714H, BAS-762H, BAS-776H, beflubutamide, benazoline, benazolin-ethyl, benfluralin, Benfuresate, Bensulide, Bensulfuron-methyl, Bentazone, Benzofendizone, Benzobicyclone, Benzofluor, Benzoylprop, Bifenox,

Bilanafos, Bilanafos sodium, Bispyribac, Bispyribac sodium, Bromacil, Bromobutide, Bromofenoxime, Bromoxynil, Bromuron, Buminafos, Busoxinone, Butachlor, Butafenacil, Butamifos, Butenachlor, Butraline, Butroxydim, Butylates, Carbamides, Chlomethoxyfen, Chloramben, Chlorazifop, Chlorazifop- butyl, chlorobromuron, chlorobufam, chlorfenac, chlorfenac sodium, chlorfenprop, chlorofluorol,

Chlorofurulomethyl, Chloridazon, Chlorimuron, Chlorimuron-ethyl, Chlormequat-chloride, Chlornitrofen, Chlorophthalim, Chlorthal-dimethyl, Chlorotoluron, Chlorsulfuron, Cinidon, Cinidon-ethyl, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop Clodinafop-propargyl, Clofencet, Clomazone, Clomeprop , Cloprop, Clopyralid, Cloransulam, Cloransulam-methyl, Cumyluron, Cyanamide, Cyanazine, Cyclanilide, Cycloate, Cyclosulfamuron, Cycloxydim, Cycluron, Cyhalofop, Cyhalofop-butyl, Cyperquat, Cyprazine, Cyprazole, 2,4-D, 2,4-DB . Daimurone / dymron, dalapon, daminozide, dazomet, n-decanol, desmedipham, desmetryne, detosyl-pyrazolate (DTP), dialkylate, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam , Diethatyl, Diethatyl-ethyl, Difenoxuron, Difenzoquat, Diflufenican, Diflufenzopyr, Diflufenzopyr- sodium, Dimefuron, Dikegulac sodium, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimethenamid-P, Dimethipin, Dimetrasulfuron, Dinitramine, Dinoseb, Dinoterb, Diphenamid , Dipropetryn, Diquat, Diquat-dibromide, Dithiopyr, Diuron, DNOC, Eglinazine-ethyl, Endothal, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron-methyl, Ethephon, Ethidimuron, Ethiozine, Ethofumesate, Ethoxyfen, Ethoxyfen-ethyl, Ethoxysulfuron, Etobenzanide, Fenoprop , Fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenuron, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P butyl, Fluca rbazone, flucarbazone sodium, flucetosulfuron, fluchloralin, flufenacet (thiafluamide), flufenpyr, flufenpyrethyl, flumetralin, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazine,

Flumipropyne, Fluometuron, Fluorodifen, Fluoroglycofen, Fluoroglycofen-ethyl, Flupoxam, Flupropacil, Flupropanate, Flupyrsulfuron, Flupyrsulfuron-methyl-Sodium, Flurenol, Flurenol-butyl, Fluridone, Flurochloridone, Fluroxypyr, Fluroxypyr-meptyl, Flurprimidol, Flurtamone, Fluthiacet, Fluthiacet- methyl, fluthiamide, fomesafen, foramsulfuron, forchlorfenuron, fosamine, furyloxyfen, gibberellin, glufosinate, glufosinate-ammonium glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-isopropylammonium, H-9201, halosafen, halosulfuron , Halosulfuron-methyl, Haloxyfop, Haloxyfop-P, Haloxyfopethoxyethyl, Haloxyfop-P-ethoxyethyl, Haloxyfop-methyl, Haloxyfop-P-methyl, Hexazinone, HNPC-9908, HW-02, Imazosulfuron, Inabenfide, Indanofan,

Indole acetic acid (IAA), 4-indol-3-yl-butyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, loxynil, isocarbamide, isopropalin, isoproturon, isoxaflutole, isoxapyrifop, KUH-043, KUH-071, carbutilate, ketospiradox, lactofen, Lenacil, linuron, maleic hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, mecopropbutotyl, mecoprop-p-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, Mecoprop-P-potassium, mefenacet, mefluidide, mepiquat chloride, mesosulfuron, mesosulfuron-methyl, mesotrione, Methabenzthiazuron, Metam, Metamifop, Metamitron, Metazachlor, Methoxyphenones, Methyldymron, 1-Methylcyclopropene, Methylisothiocyanate, Metobenzuron, Metobromuron, Metolachlor, S-Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron, Metsulfuron-methyl, Molinates, Monalides, Monocarbamides, Monocarbamides dihydrogen sulfate, monolinuron, monosulfuron, monuron, MT 128, MT-5950, ie N- [3-chloro-4- (1-methylethyl) phenyl] -2-methylpentanamide, NGGC-011, naproanilides, napropamide, naptalam, neburon, Nicosulfuron, Nipyraclofen, Nitraline, Nitrofen, Nitrophenolat-Sodium (isomeric mixture), Nitrofluorfen, Nonanoic Acid, Norflurazon, Orbencarb, Orthosulfamuron, Oryzalin, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat, Paraquat-Dichlorid, Pelargonic Acid

(Nonanoic acid), Pendimethalin, Pendralin, Penoxsulam, Pentanochlor, Pentoxazone, Perflυidone, Pethoxamide, Phenisopham, Phenmedipham, Phenmediphamethyl, Picloram, Picolinafen, Pinoxaden, Piperophos, Pirifenop, Pirifenopbutyl, Pretilachlor, Primisulfuron, Primisulfuron-methyl, Probenazole, Procyazine, Prodiamine, Prifluralin, Profoxydim, Prohexadione, Prohexadione-calcium, Prohydrojasmone, Prometon, Prometry, Propachlor, Propanil, Propaquizafop, Propazine, Propham, Propisochlor, Propoxycarbazone, Propoxycarbazone-Sodium, Propyzamide, Prosulfine, Prosulfocarb, Prosulfuron, Prynachlor, Pyraclonil, Pyrazosulfuron-ethyl, pyribambenz, pyribambenz-isopropyl, pyribenzoxime, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl,

Pyrimisulfan, Pyrithiobac, Pyrithiobac Sodium, Pyroxsulam, Quinclorac, Quinmerac, Quinoclamine, Quizalofop, Quizalofop-ethyl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Rimsulfuron, Saflufenacil, Secbumeton, Sethoxydim, Siduron, Simazine, Simetryn, SN-106279, Sulcotrione, Sulphates (CDEC), Sulfometuron, Sulfometuron-methyl, Sulfosate (Glyphosate-trimesium), Sulfosulfuron, SYN-449, SYN-523, SYP-249, SYP-298, SYP-300, Tebutam, Tebuthiuron, tecnazenes, tefuryltriones, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumetone, terbuthylazine, terbutryn, TH-547, thenylchloro, thiafluamides, thiazafluron, thiazopyr, thidiazimine, thidiazuron, thiencarbazones, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, Thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane, Trietazines, trifloxysulfuron, trifloxysulfuron sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, trimeturon, trinexapac, trinexapac-ethyl, tritosulfuron, Tsitodef, Uniconazole-P, Vernolate, ZJ-0166, ZJ-0270, ZJ-0543, ZJ-0862, and the like the following connections

Of particular interest is the selective control of harmful plants in crops of commercial and ornamental plants. Although the herbicides (A) and (B) already have good to sufficient selectivity in many cultures, phytotoxicities on the crop plants can in principle occur in some crops and, above all, in the case of mixtures with other herbicides which are less selective. In this regard, of particular interest are combinations of herbicides (A) and (B) which contain the herbicidally combined active ingredients and one or more safeners according to the invention. The safeners, which are used in an antidote effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, eg in economically important crops such as cereals (wheat, barley, rye, oats, corn, rice, millet), sugar beet, sugarcane, rapeseed , Cotton, soy or in fruit growing plants (Plantation cultures), preferably cereals, especially rice.

The following groups of compounds are suitable, for example, as safeners

(including possible stereoisomers and esters or salts commonly used in agriculture):

benoxacor

Cloquintocet (-mexyl)

cyometrinil

Cyprosulfamide Dichlormid

dicyclonon

Dietholate

Disulfonate (= O, O-diethyl S-2-ethylthioethyl phosphorodithioate)

Fenchlorazole (-ethyl) fenclorim

flurazole

fluxofenim

furilazole

Isoxadifen (-ethyl) Mefenpyr (-diethyl)

Mephenate

Naphthalic anhydrides

oxabetrinil

"R-29148" (= 3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine), "R-28725" (= 3-dichloro-acetyl-2,2, -dimethyl-1,3-oxazolidine) , "PPG-1292" (= N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide), MDKA-24 "(= N-allyl-N-kallylaminocarbonyl) -methyl-dichloroacetamide ), "AD-67" or "MON 4660" (= 3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane), "TI-35" (= 1-dichloroacetyl-azepane),

"Dimepiperate" or "MY-93" (= piperidine-1-thiocarboxylic acid S-1-methyl-1-phenylethyl ester),

"Daimurone" or "SK 23" (= 1- (1-methyl-1-phenylethyl) -3-p-tolyl-urea), "Cumyluron" = "JC-940" (= 3- (2-chlorophenylmethyl) -1- (1 _: methyl-1-phenylethyl) urea),

"Methoxyphenone" or "NK 049" (= S.β'-dimethy-W-methoxy-benzophenone),

"CSB" (= 1-bromo-4- (chloromethylsulfonyl) benzene) "CL-304415" (= 4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid; CAS Regno:

31541-57-8)

"MG-191" (= 2-dichloromethyl-2-methyl-1,3-dioxolane)

"MG-838" (= 2-propenyl 1-oxa-4-azaspiro [4.5] decane-4-carbodithioate; CAS Regno:

133993-74-5)

Methyl (diphenylmethoxy) acetate (CAS Regno: 41858-19-9 from WO-A-1998/38856)

Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Regno:

205121 -04-6 from WO-A-1998/13361)

1, 2-dihydro-4-hydroxy-1-methyl-3- (5-tetrazolyl-carbonyl) -2-quinolone (CAS Regno: 95855-00-8 from WO-A-1999/000020),

Some of the safeners are already known as herbicides and therefore, in addition to the herbicidal effect on harmful plants, also have a protective effect on the crop plants.

The weight ratio of herbicide combination to safener generally depends on the application rate of herbicide and the efficacy of the particular safener and may vary within wide limits, for example in the range of 90,000: 1 to 1: 5000, preferably 7000: 1 to 1: 1600 , in particular 3000: 1 to 1: 500. The safeners can be formulated analogously to the compounds of the formula (I) or mixtures thereof with other herbicides / pesticides and provided and used as finished formulation or tank mixture with the herbicides or used separately as seed, soil or foliar application.

The herbicidal combinations according to the invention (= herbicidal agents) have an excellent herbicidal activity against a broad spectrum economically important monocotyledonous and dicotyledonous harmful plants such as weeds, grass weeds or cyperaceans, including species which are resistant to herbicidal active substances such as glyphosate, glufosinate, atrazine, imidazolinone herbicides, sulphonylureas, (hetero) aryloxyaryloxyalkylcarboxylic acids or phenoxyalkylcarboxylic acids (so-called 'Fops'), cyclohexanedionoximes (so-called 'dims') or auxin inhibitors. Even difficult to control perennial harmful plants, which expel from rhizomes, rhizomes or other permanent organs are well detected by the active ingredients. The substances can be applied, for example, in pre-sowing, pre-emergence or post-emergence processes, for example jointly or separately. For example, the application is postemergence, in particular on the accumulated harmful plants.

Specifically, by way of example, some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.

On the side of the monocotyledonous weeds, e.g. Avena spp., Alopecurus spp., Apera spp., Brachiaria spp., Bromus spp., Digitaria spp., Lolium spp., Echinochloa spp., Leptochloa spp., Fimbristylis spp., Panicum spp., Phalaris spp., Poa spp ., Setaria spp. and Cyperus species from the annuelle group and on the part of the perennial species Agropyron, Cynodon, Imperata and Sorghum and also perennial Cyperusarten well. In dicotyledonous weed species, the spectrum of activity extends to species such as e.g. Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp., Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp., Pharitis spp., Polygonum spp., Sida spp., Sinapis spp , Solanum spp., Stellaria spp., Veronica spp. Eclipta spp., Sesbania spp., Aeschynomene spp. and Viola spp., Xanthium spp., on the annual side, as well as Convolvulus, Cirsium, Rumex, and Artemisia in perennial weeds.

Be the active ingredients of the herbicidal combinations according to the invention before the Germination of germs onto the surface of the earth either completely prevents weeds from sprouting or the weeds grow up to the cotyledon stage, but then ceases to grow and eventually completely dies after two to four weeks.

Upon application of the active ingredients to the green parts of the plants postemergence also occurs very quickly after treatment, a drastic halt in growth and the weed plants remain in the existing stage of application growth stage or die after a certain time completely, so that in this way one for the crops harmful weed competition is eliminated very early and sustainably. The active ingredients can also be applied in rice in the water and are then absorbed by soil, shoot and root.

The herbicide combinations according to the invention are distinguished by a rapidly onset and long-lasting herbicidal action. The rainfastness of the active ingredients in the combinations according to the invention is generally favorable. A particular advantage is the fact that the effective and used in combinations combinations of compounds (A) and (B) can be set so low that their soil effect is optimally low. Thus, their use is not only possible in sensitive cultures, but groundwater contaminations are virtually avoided. By the combinations of active ingredients according to the invention a significant reduction of the required application rate of the active ingredients is made possible.

In a preferred embodiment, the herbicidal combinations of the herbicides (A) and (B) according to the invention are outstandingly suitable for the selective control of harmful plants in rice crops. These include all kinds of rice cultivation in a variety of conditions, such as dry (upland, dry) or paddy, whereby irrigation is natural (rainfall) and / or artificial (irrigated, "flooded") can take place. The rice used here may be conventionally grown seed, hybrid seed, but also resistant, at least tolerant, seed (mutagenic or transgenic generated), which can be derived from the indica or Japonica and from the crossings of the two.

The herbicide combinations according to the invention can be used in all types of administration which are customary for rice herbicides. They are particularly advantageously used in the spray application and / or in the "submerged application". In the so-called "submerged application", the accumulation water already covers the soil by up to 3 -20 cm at the time of application. The herbicidal combinations of the invention are then directly, e.g. in the form of a granulate in the water of the accumulated fields. Worldwide, the spray application is mainly used for seeded rice and the so-called submerged application, mainly for transplanted rice.

The herbicide combinations according to the invention capture a broad weed spectrum which is specific for rice crops in particular. On the side of the monocotyledonous weeds, e.g. Genera, such as Echinochloa spp., Panicum spp., Poa spp., Leptochloa spp., Brachiaria spp., Digitaria spp., Setaria spp. Cyperus spp., Monochoria spp., Fimbristylis spp., Sagittaria spp., Eleocharis spp., Scirpus spp., Alisma spp., Aneilema spp., Blyxa spp., Eriocaulon spp., Potamogeton spp. and the like, in particular the species Echinochloa oryzicola, Monochoria vaginalis, Eleocharis acicularis, Eleocharis kuroguwai, Cyperus difformis, Cyperus serotinus, Sagittaria pygmaea, Alisma canaliculatum, Scirpus juncoides. In the dicotyledonous weeds, the spectrum of action extends to genera, e.g. Polygonum spp., Rorippa spp., Rotala spp., Lindernia spp., Bidens spp., Sphenoclea spp., Dopatrium spp., Eclipta spp., Elatine spp., Gratiola spp., Lindernia spp., Ludwigia spp., Oenanthe spp , Ranunculus spp., Deinostema spp. and similar. Species such as Rotala indica, Sphenoclea zeylanica, Lindernia procumbens, Ludwig prostrate, Potamogeton distinctus, Elatine triandra, Oenanthe javanica are well detected.

When herbicides of group (A) and group (B) are used together, superadditive (= synergistic) effects preferably occur. It is the Effect in the combinations stronger than the expected sum of the effects of the individual herbicides used. The synergistic effects allow a reduction of the application rate, the control of a broader spectrum of weeds, grass weeds and Cyperaceae, a faster use of herbicidal activity, a longer lasting effect, a better control of harmful plants with only one or a few applications and an extension of the possible period of application , In part, the use of combinations also reduces the amount of harmful ingredients, such as nitrogen or oleic acid, and their entry into the soil.

The said properties and advantages are required in practical weed control in order to keep agricultural / forestry / horticultural crops or grassland / pasture areas free of undesired competing plants and thus to secure and / or increase yields qualitatively and quantitatively. The technical standard is significantly exceeded by these new herbicide combinations in terms of the properties described.

On account of their herbicidal and plant growth-regulating properties, the herbicidal combinations according to the invention can be used for controlling harmful plants in known plant crops or tolerant or genetically modified crop and energy crops to be developed. The transgenic plants (GMOs) are usually distinguished by particular advantageous properties, in addition to the resistance to the herbicidal combinations according to the invention, for example, by resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties concern, for example, the crop in terms of quantity, quality, shelf life, and the composition of special ingredients. Thus, transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop or increased vitamin content or energy properties are known. equally The active compounds can also be used for controlling harmful plants in crops of known or yet to be developed by mutant selection plants, as well as from crosses of mutagenic and transgenic plants due to their herbicidal and plant growth regulatory properties.

Well-known routes for the production of new plants which have modified properties compared to previously occurring plants consist, for example, in classical breeding methods and the production of mutants. Alternatively, new plants with altered properties can be generated by genetic engineering techniques (see, e.g., EP-A-0221044, EP-A-0131624). For example, in several cases, genetic modifications of crop plants have been described for the purpose of modifying the starch synthesized in the plants (eg WO 92/11376, WO 92/14827, WO 91/19806), transgenic crop plants which have resistance to herbicides, for example to sulfonylureas (EP -A-0257993, US-A-5013659), transgenic crops having the ability

To produce Bacillus thuringiensis toxins (Bt toxins) which render plants resistant to certain pests (EP-A-0142924,

EP-A-0193259). Transgenic crop plants with modified fatty acid composition (WO 91/13972).

Numerous molecular biology techniques that can be used to produce novel transgenic plants with altered properties are known in principle; See, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Ed. CoId Spring Harbor Laboratory Press, ColD Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996 or Christou, "Trends in Plant Science" 1 (1996) 423-431). For such genetic engineering, nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. With For example, base substitutions can be made, partial sequences removed, or natural or synthetic sequences added using the standard procedures outlined above. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments.

The production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.

For this purpose, DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product but are not completely identical.

In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. However, to achieve localization in a particular compartment, e.g. the coding region is linked to DNA sequences 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., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

The transgenic plant cells can be whole by known techniques

Plants are regenerated. In principle, the transgenic plants can be plants of any plant species, ie monocotyls as well also dicotyledonous plants. Thus, transgenic plants are available which have altered properties by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.

The present invention furthermore relates to a method for the selective control of undesirable plants, preferably in plant crops, in particular in rice crops (planted or sown under 'upland ¹ or' paddy ¹ conditions with indica and / or japonica species and hybrids / mutants / GMOs), characterized in that the herbicides as components (A) and (B) of the herbicidal combinations according to the invention on the plants (eg harmful plants such as monocotyledonous or dicotyledonous weeds, weed grasses, cyperaceans or undesirable crops), the seed ( For example, grains, seeds or vegetative propagules such as tubers or Sprossteile with buds) or the area on which the plants grow (eg the acreage, which may also be covered by water) are applied, for example, together or separately. One or more herbicides (A) may be applied before, after or simultaneously with the herbicide (s) (B) to the plants, seed or area on which the plants grow (eg the area under cultivation).

Undesirable plants are understood to mean all plants that grow in places where they are undesirable. This can e.g. Harmful plants (e.g., monocotyledonous or dicotyledonous weeds, weed grasses, cyperaceans or undesirable crops), e.g. also those which are active against certain herbicidal active ingredients such as glyphosate, glufosinate, atrazine, imidazolinone herbicides, sulfonylureas, (hetero-) aryloxy-aryloxyalkylcarboxylic acids or -phenoxyalkylcarboxylic acids (so-called 'fops'), cyclohexanedionoximes (so-called 'dims') or auxin inhibitors are resistant.

The herbicide combinations according to the invention will be used selectively for controlling undesired plant growth, for example in crops such as field crops eg monocotyledonous crops such as cereals (eg wheat, barley, rye, oats, rice, maize, millet) or dicotyledonous crops such as Sugarbeet, sugarcane, oilseed rape, cotton, sunflowers and legumes eg of the genera Glycine (eg Glycine max. (Soy) as non-transgenic Glycine max. (Eg conventional strains like STS strains) or transgenic Glycine max (eg RR- soybean or LL soybean) and their crosses), Phaseolus, Pisum, Vicia and Arachis, or vegetable crops from various botanical groups such as potato, leek, cabbage, carrot, tomato, onion, in orchards (plantation crops), green, lawn and pasture or on non-cultivated areas (eg squares of residential and industrial plants, railway tracks), in particular in rice crops (planted or sown under 'Upland ¹ or' Paddy 'conditions with Indica and / or Japonica species as well as hybrids / mutants / GMOs) , The application is carried out both before the emergence of harmful plants and on the accumulated harmful plants (eg weeds, grass weeds, Cyperaceans or undesirable crops) regardless of the stage of sown / planted culture.

The invention also relates to the use of the herbicide combinations according to the invention for the selective control of undesired plant growth, preferably in plant crops, in particular in rice crops (planted or sown under 'upland' or 'paddy' conditions with indica and / or Japonica species as well as hybrids / mutants / GMOs).

The herbicidal combinations according to the invention can be prepared by known processes, for example as mixed formulations of the individual components, optionally with further active ingredients, additives and / or customary formulation auxiliaries, which are then diluted with water for use in the usual way, or as so-called tank mixtures by joint dilution separately formulated or partially separately formulated components with water. Also possible is the staggered use (split application, splitting) of the separately formulated or partially separately formulated individual components. It is also possible to use the herbicides or the herbicide combinations in several portions (sequence application), eg after applications as seed treatment or pre-seed (plant) treatment or pre-emergence, followed by post-emergence applications or after early application Post-emergence applications followed by mid-late post-emergence applications. Preference is given to the common or timely use of the active ingredients of the respective combination, particularly preferably the common use.

The herbicides (A) and (B) can be converted together or separately into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, microencapsulations in polymeric substances. Also to be mentioned are specific formulations for rice cultivation, such as e.g. Scattering granules, "jumbo" granules, "floating granules", "floating" -suspoemulsions which are applied via "shaker bottles" and are dissolved and distributed via the accumulation water. The formulations may contain the usual auxiliaries and additives.

These formulations are prepared in a known manner, e.g. by

Mixing the active compounds with extenders, that is to say liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.

In the case of the use of water as extender, for example, organic solvents can also be used as auxiliary solvent. Suitable liquid solvents are essentially: aromatics, such as XyIoI ₁ toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes, or methylene chloride, aliphatic

Hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulfoxide, and water.

Suitable solid carriers are: for example, ammonium salts and natural Minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates; as solid carriers for granules are: for example, broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corncobs and tobacco stalks; suitable emulsifiers and / or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates,

Arylsulfonates and protein hydrolysates; suitable dispersants are: e.g. Ligninsulfitablaugen and methylcellulose.

Adhesives such as carboxymethylcellulose, natural and synthetic, powdery, granular or latex polymers may be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Other additives may be mineral and vegetable oils.

The herbicidal action of the herbicidal combinations according to the invention can be improved, for example, equally by surface-active substances, preferably by wetting agents from the series of fatty alcohol polyglycol ethers. The fatty alcohol polyglycol ethers preferably contain 10 to 18 C atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether section. The fatty alcohol polyglycol ethers can be nonionic or ionic, for example in the form of fatty alcohol polyglycol ether sulfates, are present, the (eg sodium and potassium salts) or ammonium salts, or as alkaline earth metal salts are used for example as alkali metal salts, such as C ₁₂ / C ₄ fatty alcohol diglykolethersulfat- sodium (Genapol ^® LRO, Clariant GmbH); See, for example, EP-A-0476555, EP-A-0048436, EP-A-0336151 or US-A-4,400,196 and Proc. EWRS Symp. "Factors Affecting Herbicidal Activity and Selectivity", 227-232 (1988). Nonionic fatty alcohol polyglycol ethers are, for example, 2 to 20, preferably 3 to 15, Ethylene oxide units containing (C-io Ciβ) -, preferably (Ci ₀ - Ci ₄ ) -fatty alcohol polyglycol ether (eg isotridecyl alcohol polyglycol ether) eg from the Genapol ^® X series such as Genapol ^® X-030, Genapol ^® X-060, Genapol ^® X-080 or Genapol ^® X-150 (all from Clariant GmbH).

The present invention further comprises the combination of components (A) and (B) with the aforementioned wetting agents from the series of fatty alcohol polyglycol ethers which preferably contain 10 to 18 C atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether part and nonionic or ionic (eg as fatty alcohol polyglycol ether) may be present. Preferred are

C ₂ / C ₄ fatty alcohol diglycol ether sulfate sodium (Genapol ^® LRO, Clariant GmbH) and isotridecyl alcohol polyglycol ether having 3-15 ethylene oxide units, for example from the Genapol ^® X series, such as Genapol ^® X-030, Genapol ^® X-060 , Genapol ^® X-080 and Genapol ^® X-150 (all from Clariant GmbH).

Furthermore, it is known that fatty alcohol polyglycol ethers such as nonionic or ionic fatty alcohol polyglycol ethers (e.g., fatty alcohol polyglycol ether sulfates) are also useful as penetration aids and enhancers for a variety of other herbicides (see, e.g., EP-A-0502014). The present invention therefore furthermore also includes the combination with suitable penetration aids and activity enhancers, preferably in a commercially available form.

The herbicide combinations according to the invention can also be used together with vegetable oils. The term vegetable oils refers to oils from oil-supplying plant species such as soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, thistle oil or castor oil, in particular rapeseed oil, and their transesterification products, e.g. Alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.

The vegetable oils are preferably esters of Ci ₀ -C ₂₂ -, preferably CI ₂ -C ₂₀ -

Fatty acids. The Ci _O -C ₂₂ fatty acid esters are, for example, esters of unsaturated or saturated Cio-C ₂₂ -fatty acids, in particular having an even number of carbon atoms, for example Erucic acid, lauric acid, palmitic acid and especially C ₁₈ fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.

Examples of Ci _O -C ₂₂ fatty acid esters are esters obtained by reacting glycerol or glycol with the C _O -C ₂₂ fatty acids, such as those contained in oils from oil-plant species, for example, or Ci-C ₂ o Alkyl CioC ₂₂ fatty acid esters, as obtained, for example, by transesterification of the aforementioned glycerol or glycol-C- ₀ -C ₂₂ fatty acid esters with CrC ₂ o-alcohols (eg, methanol, ethanol, propanol or butanol) can be. The transesterification can be carried out by known methods, as described for example in Rompp Chemie Lexikon, 9th edition, Volume 2, page 1343, Thieme Verlag Stuttgart.

Preferred as CrC ₂ o-alkyl-Cio-C ₂₂ fatty acid esters are methyl esters, ethyl esters, propyl esters, butyl esters, 2-ethylhexyl esters and dodecyl esters. Preferred glycol and glycerol-Cio-C ₂₂ fatty acid esters are the uniform or mixed glycol esters and glycerol esters of C ₁₀ -C ₂₂ fatty acids, in particular those having even numbers of carbon atoms, eg erucic acid, lauric acid, palmitic acid and in particular C. -is fatty acids such as stearic acid, oleic acid, linoleic acid or linolenic acid.

The vegetable oils can be present in the inventive herbicidal compositions, for example in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil such as Hasten ^® (Victorian Chemical Company, Australia, hereinbelow termed Hasten, main ingredient: rapeseed oil ethyl ester), Actirob ^® B (Novance, France, hereinafter ActirobB called, main component:

Called Rapsölmethylester), Rako-Binol ^® (Bayer AG, Germany, referred to as Rako-Binol, main ingredient: rapeseed oil), Renol ^® (Stefes, hereinafter referred to Germany Renol, vegetable oil ingredient: Rapsölmethylester) or Stefes Mero ^® (Stefes, Germany, termed Mero called, main component: rapeseed oil methyl ester) may be included.

The present invention also includes in another embodiment Combinations with the mentioned vegetable oils such as rapeseed oil, preferably commercially available in the form of oil-containing formulation additives, 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, hereinafter referred to ActirobB, main component:

Called Rapsölmethylester), Rako-Binol ^® (Bayer AG, Germany, referred to as Rako-Binol, main ingredient: rapeseed oil), Renol ^® (Stefes, hereinafter referred to Germany Renol, vegetable oil ingredient: Rapsölmethylester) or Stefes Mero ^® (Stefes, Germany, termed Mero called, main component: rapeseed oil methyl ester).

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations generally contain between 0.1 and 95 weight percent (wt%) of active ingredient, preferably between 0.5 and 90 wt%.

The herbicides (A) and (B) can be used as such or in their formulations also in admixture with other agrochemical active substances such as known herbicides for controlling undesired plant growth, e.g. for weed control or to control undesirable crops, e.g. Ready-to-use formulations or tank mixes are possible.

Mixtures with other known active substances such as fungicides, insecticides, acaricides, nematicides, safeners, bird repellants, plant nutrients and soil conditioners are also possible.

The herbicides (A) and (B) can be used as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and Granules are applied. The application is done in the usual way, eg by pouring, spraying, spraying, spreading.

The active substances can be applied to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds, weed grasses, cyperaceans or undesired crop plants), the seeds (for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds) or the cultivated area (for example arable soil) , preferably on the green plants and plant parts and optionally on the farmland. One possibility of the application is the common application of the active ingredients in the form of tank mixes, wherein the optimally formulated concentrated formulations of the individual active ingredients are mixed together in the tank with water and the spray mixture obtained is applied.

A common herbicidal formulation of the combination of herbicides (A) and (B) according to the invention has the advantage of easier applicability, wherein the amounts of the components can be adjusted already in the optimal ratio to each other. In addition, the adjuvants in the formulation can be optimally matched to one another.

Biological examples

Weed effect in postemergence

method

Seeds or rhizome pieces of monocotyledonous and dicotyledonous crops and useful plants were laid out in peat pots (4 cm in diameter) filled with sandy loam soil and then covered with soil. The pots were kept in the greenhouse under optimal conditions. In addition were

Cloves that are found in paddy rice cultivation, cultivated in pots with a water level 2 cm above the soil surface. About three weeks after the beginning of the cultivation, the test plants were treated at the 2- to 3-leaf stage. The herbicides, formulated as powder or liquid concentrates, were sprayed either alone or in the combinations according to the invention with a water application rate of 600 l / ha in different dosages onto the green plant parts. Subsequently, the pots were kept for further cultivation of the plants under optimal conditions in the greenhouse.

The visual evaluation of the herbicidal effects took place at intervals up to 21 days after the treatment. The evaluation was carried out on a percentage basis in comparison to the untreated control plants: 0% = no herbicidal action, 100% = complete herbicidal action = complete kill.

The percentage data from the treatments with the herbicides alone (= single applications) and with the combinations according to the invention (= mixtures) were used to calculate interactions according to the method of Colby. If the observed effect values of the mixtures already exceed the formal sum of the values for the experiments with single applications, then they also exceed Colby's expectation value, which is calculated according to the following formula (see SR Colby, in Weeds 15 (1967) p 22):

E = A + B - (A x B / 100)

Where:

A, B = effect of component A or B in percent at a dosage of a or b g ai / ha (= grams of active ingredient per hectare). E = expected value in% at a dosage of a + b g ai / ha.

Results

The inventive combinations of herbicides from group (A) with Group B herbicides have been tested on a wide range of important weeds (weed grass / weeds / Cyperaceae) and crops: Triticum aestivum (TRZAS), Stellaria media (STEME), Lolium multiflorum (LOLMU), Veronica persica (VERPE), Alopecurus myosuroides (ALOMY), Matricaria inodora (MATIN), Brassica napus (BRSNW), Viola tricolor (VIOTR), Avena fatua (AVEFA), Amaranthus retroflexus (AMARE), Zea mays (ZEAMX), Pharbitis purpurea (PHBPU), Setaria viridis ( SETVI), Fallopia (ex Polygonum) convolvulus (POLCO), Echinochloa crus-galli (ECHCG), Abuthilon theophrasti (ABUTH), Cyperus esculentus (CYPES), Oryza sativa (ORYSA).

Particularly noteworthy are the results shown in the following tables (Tab.) Using the following legend:

(1) EPPO Code (formerly Bayer Code) for treated plant (see above) (2) Evaluation time: DAT (days after treatment)

(3) Tested Component A (Identification of Code)

(4) Tested Component B (Identification of Code)

(5) Dosage Component A [g ai / ha]

(6) Dosage Component B [g ai / ha] (7)% activity found

(8) value E (calculated according to Colby, see above)

(9) Comment: "SYNERGY" = synergistic interaction (value E <% effect found); "SAFENING" = safener effect on crop (value E>% effect found)

Tab.1: (1) LOLMU - (2) 10 DAT - Tab.5: (1) ZEAMX - (2) 10 DAT - (3) A-1- (4) B1-6 (3) A-1 (4) B1-6

(9) SYNERGY (9) SYNERGY

Tab.2: (I) LOLMU - (2) 10 DAT- 20 Tab.6: (1) ORYSA - (2) 10 DAT - (3) A-1 - (4) B1-6 (3) A-1 - (4) B1-6

(9) SAFENING

(9) SYNERGY

Table 7: (1) LOLMU - (2) 21 DAT

Table 3: (1) ALOMY - (2) 10 DAT 25 (3) A-1 - (4) B1-6 (3) A-1 - (4) B1-6

(9) SYNERGY

Table 8: (1) ALOMY - (2) 21 DAT

(9) SYNERGY (3) A-1 - (4) B1-6

Table 4: (1) AVEFA - (2) 10 DAT (3) A-1 - (4) B1-6

30 (9) SYNERGY (9) SYNERGY Tab.9: (1) MATIN - (2) 21 DAT - Tab.12: (1) SETVI - (2) 21 DAT - (3) A-1- (4) B1-6 (3) A-1 (4) B1-6

(9) SYNERGY 15 (9) SYNERGY

Table 13: (1) POLCO - (2) 21 DAT - Table 10: (1) AVEFA - (2) 21 DAT (3) A-1- (4) B1-6 (3) A-1 ( 4) B1-6

(9) SYNERGY

20 Tab.14: (1) POLCO - (2) 21 DAT

Table 11: (I) ZEAMX - (2) 21 DAT (3) A-1 - (4) B1-6 (3) A-1- (4) B1-6

(9) SYNERGY

Tab.15: (1) ORYSA - (2) 21 DAT - Tab.19: (1) ALOMY - (2) 10 DAT - (3) A-1 - (4) B1-6 (3) A-1 - (4) B3-3

(9) SAFENING (9) SYNERGY

Tab.16: (I) TRZAS - (2) 10 DAT- 20 Tab.20: (1) ORYSA - (2) 10 DAT - (3) A-1 - (4) B3-3 (3) A-1 - (4) B3-3

(9) SYNERGY

Table 21: (1) TRZAS - (2) 21 DAT - 25 (3) A-1 - (4) B3-3

Table 17: (1) TRZAS - (2) 10 DAT (3) A-1 - (4) B3-3

(9) SYNERGY (9) SYNERGY

Tab.18: (1) LOLMU - (2) 10 DAT - Tab.22: (1) TRZAS - (2) 21 DAT - (3) A-1 - (4) B3-3 (3) A-1 - (4) B3-3

(9) SYNERGY 30 (9) SYNERGY Table 23: (1) LOLMU - (2) 21 DAT - Table 26: (1) ZEAMX - (2) 21 DAT - (3) A-1 - (4) B3-3 (3) A-1 - (4) B3-3

15 (9) SYNERGY

Table 27: (1) POLCO - (2) 21 DAT (3) A-1 - (4) B3-3

(9) SYNERGY

Table 24: (1) ALOMY - (2) 21 DAT (3) A-1 - (4) B3-3

(9) SYNERGY

20

Table 28: (1) CYPES - (2) 21 DAT (3) A-1 - (4) B3-3

(9) SYNERGY

Table 25: (1) ZEAMX - (2) 21 DAT (3) A-1 - (4) B3-3

(9) SYNERGY

25 Tab.29: (1) ORYSA - (2) 10 DAT (3) A-1 - (4) B4-2

(9) SYNERGY

(9) SAFENING Table 30: (1) LOLMU - (2) 21 DAT - Tab. 34: (1) ZEAMX - (2) 21 DAT - (3) A-1 - (4) B4-2 (3) A-1 - (4) B4-2

(9) SYNERGY Tab. 31: (1) VIOTR - (2) 21 DAT - (3) A-1 - (4) B4-2

20 Tab. 35: (1) CYPES - (2) 21 DAT (3) A-1 - (4) B4-2

(9) SYNERGY

Table 36: (1) ORYSA - (2) 21 DAT

Table 32: (1) AVEFA - (2) 21 DAT 25 (3) A-1 - (4) B4-2 (3) A-1 - (4) B4-2

(9) SAFENING

(9) SYNERGY

Table 37: (1) TRZAS - (2) 10 DAT

Table 33: (1) ZEAMX - (2) 21 DAT (3) A-1 - (4) B5-2 (3) A-1 - (4) B4-2

30 (9) SYNERGY (9) SYNERGY Table 38: (1) LOLMU - (2) 10 DAT - Table 42: (1) ALOMY - (2) 21 DAT - (3) A-1 - (4) B5-2 (3) A-1 - (4) B5-2

(9) SYNERGY (9) SYNERGY

20 Tab.39: (1) ZEAMX - (2) 10 DAT Tab.43: (1) MATIN - (2) 21 DAT (3) A-1 - (4) B5-2 (3) A-1 - ( 4) B5-2

(9) SYNERGY

Table 40: (1) LOLMU - (2) 21 DAT - (3) A-1 - (4) B5-2

25 Tab.44: (1) AVEFA - (2) 21 DAT (3) A-1 - (4) B5-2

(9) SYNERGY (9) SYNERGY

Table 41: (1) LOLMU - (2) 21 DAT - Table 45: (1) ZEAMX - (2) 21 DAT - (3) A-1 - (4) B5-2 30 (3) A-1 - (4) B5-2

(9) SYNERGY (9) SYNERGY Table 46: (1) TRZAS - (2) 10 DAT - Table 50: (1) MATIN - (2) 21 DAT - (3) A-1 - (4) B5-3 (3) A-1 - (4) B5-3

(9) SYNERGY

Table 47: (I) LOLMU - (2) 10 DAT (3) A-1 - (4) B5-3

(9) SYNERGY

20

Table 51: (1) AVEFA - (2) 21 DAT (3) A-1 - (4) B5-3

(9) SYNERGY

Table 48: (1) ORYSA - (2) 10 DAT (3) A-1 - (4) B5-3

(9) SYNERGY

25 Tab. 52: (1) ZEAMX - (2) 21 DAT (3) A-1 - (4) B5-3

(9) SAFENING

Table 49: (1) LOLMU - (2) 21 DAT (3) A-1 - (4) B5-3

(9) SYNERGY (9) SYNERGY Table 53: (1) ORYSA - (2) 21 DAT - 15 Tab. 57: (1) LOLMU - (2) 21 DAT (3) A-1 - (4) B5-3 (3) A-1 - (4) B6-1

(9) SAFENING (9) SYNERGY Table 54: (I) TRZAS - (2) 10 DAT - Tab. 58: (1) ALOMY - (2) 21 DAT -

Table 61: (1) ZEAMX - (2) 10 DAT - Table 65: (1) AVEFA - (2) 21 DAT - (3) A-1 - (4) B6-2 (3) A-1 - (4) B6-2

(9) SYNERGY

20 Tab.66: (1) ZEAMX - (2) 21 DAT - (3) A-1 - (4) B6-2 Tab.62: (1) ZEAMX - (2) 10 DAT (3) A-1 - (4) B6-2

(9) SYNERGY

Table 63: (1) ORYSA - (2) 10 DAT (9) SYNERGY (3) A-1 - (4) B6-2

Table 67: (1) CYPES - (2) 21 DAT 25 (3) A-1 - (4) B6-2

(9) SAFENING

Tab.64: (1) ALOMY - (2) 21 DAT - (9) SYNERGY (3) A-1 - (4) B6-2

Table 68: (1) TRZAS - (2) 10 DAT (3) A-1 - (4) B7-4

30 (9) SYNERGY (9) SYNERGY Table 69: (1) STEME - (2) 10 DAT - Tab.73: (1) ZEAMX- (2) 10 DAT - (3) A-1 - (4) B7-4 (3) A-1 - (4) B7-4

(9) SYNERGY

20

(9) SYNERGY Tab.74: (1) TRZAS - (2) 21 DAT (3) A-1 - (4) B7-4 Tab.70: (1) LOLMU - (2) 10 DAT (3) A- 1 - (4) B7-4

(9) SYNERGY

25 Tab.75: (1) VERPE - (2) 21 DAT

Table 71: (1) LOLMU - (2) 10 DAT (3) A-1 - (4) B7-4 (3) A-1 - (4) B7-4

(9) SYNERGY

Table 72: (1) VIOTR - (2) 10 DAT (3) A-1 - (4) B7-4

(9) SYNERGY Table 76: (1) MATIN - (2) 21 DAT - Table 80: (1) ZEAMX - (2) 21 DAT - (3) A-1 - (4) B7-4 (3) A-1 - (4) B7-4

(9) SYNERGY (9) SYNERGY

Table 77: (1) VIOTR - (2) 21 DAT - 20 Tab.81: (1) PHBPU - (2) 21 DAT - (3) A-1 - (4) B7-4 (3) A-1 - (4) B7-4

(9) SYNERGY

Tab.78: (1) AVEFA - (2) 21 DAT (3) A-1 - (4) B7-4

(9) SYNERGY

Table 82: (1) POLCO - (2) 21 DAT 25 (3) A-1 - (4) B7-4

(9) SYNERGY

Table 79: (1) AVEFA - (2) 21 DAT (9) SYNERGY (3) A-1 - (4) B7-4

(9) SYNERGY Table 83: (1) POLCO - (2) 21 DAT - (3) A-1 - (4) B7-4

(9) SYNERGY

Tab.84: (1) ABUTH - (2) 21 DAT (3) A-1 - (4) B7-4

(9) SYNERGY

Table 85: (1) CYPES - (2) 21 DAT - (3) A-1 - (4) B7-4

(9) SYNERGY

Claims

claims

1. A herbicidal combination comprising components (A) and (B), where (A) is one or more compounds or salts thereof from the group described by the general formula (I):

wherein R ^{1 is} halogen, preferably fluorine or chlorine,

R ^{2 is} hydrogen and R ^{3 is} hydroxyl or R ² and R ^{3, taken} together with the carbon atom to which they are attached, denote a carbonyl group C = O and

R ^{4 is} hydrogen or methyl;

and

(B) means one or more herbicides from the group of the azoles consisting of:

(B1-1) benzofenap; (B1-2) pyrazolynates;

(B1-3) pyrazoxyfen;

(B1-4) pyroxasulfones;

(B1-5) toprame zone;

(B 1-6) pyrasulfotols; (B1-7) NC-310;

(B2-1) pyrazole ethyl;

(B2-2) Fluazolates; (B3-1) isourone;

(B3-2) isoxaben;

(B3-3) isoxaflutole;

(B4-1) imazamethabenz-methyl; (B4-2) imazamox;

(B4-3) Imazapic;

(B4-4) imazapyr;

(B4-5) imazaquin;

(B4-6) imazethapyr; (B4-7) profluazole;

(B5-1) Methazoles;

(B5-2) oxadiargyl;

(B5-3) oxadiazone;

(B6-1) Amicarbazone; (B6-2) carfentrazone-ethyl;

(B6-3) sulfentrazone;

(B6-4) Bencarbazone;

(B6-5) Ioparbocarcinone;

(B7-1) amitrole; (B7-2) paclobutrazole;

(B7-3) uniconazole;

(B7-4) Cafenstrole;

(B8-1) Fentrazamide;

(B8-2) F-5231;

excluding the following combinations:

Compounds of the general formula (I) with R ¹ fluorine, R ² and R ³ carbonyl

Group C = O, R ^{4 is} methyl, and compounds B1-1 (benzofenap), B8-1 (fentrazamide).

2. A herbicidal combination according to claim 1, containing as component (A) a or more of the compounds from the following group consisting of:

Compound (A-1), Compound (A-2),

Compound (A-3),

Compound (A-4),

Compound (A-5), Compound (A-6),

Compound (A-7),

Compound (A-8).

3. A herbicidal combination according to any one of claims 1 or 2, comprising as component (B) one or more of the compounds from the group mentioned below consisting of:

(B1-1) benzofenap, (B1-4) pyroxasulfone, (B1 -5) toprame zone, (B1-6) pyrasulfotole, (B 1-7) NC-310, (B3-2) isoxaben, (B3-3) Isoxaflutole, (B4-1) imazamethabenz-methyl, (B4-2) imazamox, (B4-3) imazapic, (B4-4) imazapyr, (B4-5) imazaquin, (B4-6) imazethapyr, (B5-2 ) Oxadiargyl, (B5-3) oxadiazone, (B6-1) amicarbazone, (B6-2) carfentrazone-ethyl, (B6-3) sulfenrazone, (B6-5) isophorcarbazone, (B7-1) amitrole, (B7-) 2) Paclobutrazole, (B7-3) Uniconazole, (B7-4) Cafenstrole, (B8-1) Fentrazamide; particularly preferred (B1-1) benzofenap, (B1-4) pyroxasulfone, (B1-5) toprame zone, (B1-6) pyrasulfotole, (B3-3) isoxaflutole, (B4-2) imazamox, (B5-2) oxadiargyl , (B5-3) oxadiazone, (B6-1) amicarbazone, (B6-2) carfentrazone-ethyl, (B6-5) -propanecarbazone, (B7-4) cafenstrole, (B8-1) -fentrazamide.

A herbicidal combination according to any one of claims 1 to 3, wherein the weight ratio (A): (B) of the components (A) and (B) is generally in the range of 1: 5000 to 5000: 1, preferably 1: 3000 to 500: 1, in particular 1: 1500 to 200: 1, is located.

5. A herbicidal combination according to any one of claims 1 to 4, comprising an effective content of components (A) and (B) and / or additionally one or more further components from the group of agrochemical active ingredients of other kinds, customary in crop protection additives and formulation auxiliaries.

6. A method for controlling undesired plant growth, wherein the components (A) and (B) of the herbicide combination, defined according to one or more of claims 1 to 5, applied together or separately.

7. The method of claim 6 for controlling unwanted

Plant growth in crops such as wheat (hard and soft wheat), corn, soy, sugar beet, sugar cane cotton, rice, beans, flax, barley, oats, rye, triticale, rapeseed, potato, millet (sorghum), pasture, green / lawns , in fruit growing plants, or on non-cultivated areas, in particular in rice crops.

8. Use of the defined according to any one of claims 1 to 5 herbicide combination for combating undesirable plant growth.