DE19962017A1 - Selective herbicides based on N-aryl-triazolin (thi) onen - Google Patents

Abstract

The invention relates to novel herbicidal, synergistic active substance combinations that comprise known N-aryl-triazoline(thi)ones and known herbicidally effective compounds and/or compounds that improve the tolerability for cultivated plants. The inventive combinations are especially effective in selective weed control in various cultures of cultivated plants.

Description

The invention relates to new herbicidal, synergistic active ingredient combinations which known N-aryl-triazolin (thi) one on the one hand and known herbicidally active ver bindings and / or compounds which improve crop compatibility on the other hand include and with particularly good success to selective weeds control can be used in various crops.

N-aryl-triazolin (thi) ones are the subject of a number of herbicidally active substances of patent applications (cf. DE-A-30 24 316, DE-A-35 14 057, DE-A-36 36 318, EP- A-220952, EP-A-370332, EP-A-597360, EP-A-609734, US-A-4702763, US-A- 4806145, US-A-4818275, US-A-4906284, US-A-4909831, US-A-5035740, US-A- 5041155, WO-A-85/01637, WO-A-85/04307, WO-A-86/02642, WO-A-86/04481, WO-A-87/00730, WO-A-87/03782, WO-A-88/09617, WO-A-90/02120, WO-A- 95/30661, WO-A-99/37153). However, the known N-aryl-triazolin (thi) one a number of impact gaps.

Surprisingly, it has now been found that a number of known active ingredients substances from the series of N-aryl-triazolin (thi) one when used together with known herbicidally active compounds synergistic effects in terms of Show activity against weeds and particularly advantageous as broadly effective Combination products for the selective control of weeds in crops cultures such as B. in barley, corn, rice, soybeans, sunflowers, wheat and sugar tube can be used.

The invention relates to selective herbicidal compositions, characterized by an effective content of an active ingredient combination comprising

• 1. at least one N-aryl-triazolin (thi) on of the general formula (I)
  in which
  Q ^{1 represents} oxygen or sulfur,
  R ^{1 represents} alkyl which has 1 to 5 carbon atoms and is optionally substituted by halogen,
  R ^{2 represents} optionally substituted by halogen alkyl with 1 to 5 carbon atoms,
  R ^{3 represents} hydrogen or halogen,
  R ^{4 represents} cyano, thiocarbamoyl or halogen, and
  R ⁵ for nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, hydroxyamino, aminosulfonyl, halogen, for each optionally by cyano, hydroxy, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylcarbonyl and / or C ₁ - C ₄ -alkoxy-carbonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl or alkylamino each having 1 to 6 carbon atoms, each optionally with cyano, carboxy, halogen and / or C ₁ - C ₄ -alkoxy-carbonyl-substituted alkenyl, alkynyl, alkenyloxy or alkinyboxy, each having 2 to 6 carbon atoms, for each optionally substituted by halogen, alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, N, N-bisalkylsulfonylamino or N-alkylcarbonyl-N-alkylsulfonyl- amino each having 1 to 6 carbon atoms in the alkyl groups, or for each optionally by cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ - Halogenalkoxy substitui first N-phenylcarbonyl-N-alkylsulfonyl-amino, N-pyridylcarbonyl-N-alkylsulfonyl-amino, N-furylcarbonyl-N-alkylsulfonyl amino or N-thienylcarbonyl-N-alkylsulfonyl-amino each having 1 to 6 carbon atoms in the alkyl groups,
  ("Active substances of group 1")
  and
• 2. at least one compound from a second group of herbicides which contains the active compounds mentioned below:
  2-Chloro-N- (ethoxymethyl) -N- (2-ethyl-6-methyl-phenyl) -acetamide (acetochlor), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid sodium salt (Acifluorfen sodium), 2-chloro-6-nitro-3-phenoxy-benzenamine (Aclonifen), 2-chloro-N- (methoxy methyl) -N- (2,6-diethyl-phenyl) -acetamide (alachlor), N-ethyl-N'-i-propyl-6-methylthio-1,3,5-triazine-2,4-diamine (ametryn), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (N-methyl-N-methylsulfonylsulfamoyl) urea (amidosulfuron), 1H-1,2,4-triazol-3-amine (amitrole), 6-chloro-4-ethylamino-2-isopropylamino-1, 3,5-triazine (atrazine), N- (4,6-dimethoxypyrimidin-2-yl) -N '- [1-methyl-4- (2-methyl-2H-tetrazol-5-yl) -1H - pyrazol-5-ylsulfonyl] urea (azimsulfuron), 2- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5,6,7,8-tetrahydro-1,2,4-triazolo - [4,3-a] pyridine-3 (2H) -one (azafenidin), N-benzyl-2- (4-fluoro-3-trifluoromethyl-phenoxy) -butanamide (beflubutamide), 4-chloro-2- oxo-3 (2H) -benzthiazole acetic acid (benazoline), N-butyl-N-ethyl-2,6-dinitro-4-tri fluoromethyl-benzenamine (benflur aline), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-methoxycarbonylphenylmethylsulfonyl) urea (bensulfuron), 2- [2- [4- (3,6-dihydro -3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinylphenoxymethyl] -5-ethylphenoxypropanoic acid methyl ester (benzfendizone), 3- (2-chloro-4-methylsulfonylbenzoyl) -4- phenylthio-bicyclo- [3.2.1] oct-3-en-2-one (benzobicyclone), ethyl-N-benzoyl-N- (3,4-dichlorophenyl) -DL-alaninate (benzoylprop-ethyl), 3-i-propyl-1H-2,1,3-benzothiadiazin-4 (3H) -one (bentazone), methyl 5- (2,4-dichlorophenoxy) -2-nitro benzoate (bifenox), 2, 6-bis- (4,6-dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid sodium salt (bispyribac-sodium), 2-bromo-3,3-dimethyl-N- (1-methyl-1-phenylethyl) ) -butanamide (bromobutide), 3,5-dibromo-4-hydroxybenzaldehyde-O- (2,4-di nitro-phenyl) -oxime (bromofenoxime), 3,5-dibromo-4-hydroxy-benzonitrile (bromine oxynil) , N-butoxymethyl-2-chloro-N- (2,6-diethylphenyl) acetamide (butachlor), 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4 -trifluoromethyl-1 (2H) -pyrimidinyl) -benzoic acid- [1,1-di methyl-2-oxo-2- (2-propenyloxy)] - ethyl ester (butafenacil-allyl), 2- (1-ethoximino-propyl) -3-hydroxy-5- [2,4,6-trimethyl-3- ( 1-oxo-butyl) phenyl] -2-cy clohexen-1-one (butroxydim), S-ethyl-bis- (2-methyl-propyl) -thiocarbamate (butylate), N, N-diethyl-3- ( 2,4,6-trimethyl-phenylsulfonyl) -1H-1,2,4-triazole-1-carboxamide (cafenstrole), 2- [1 - [(3-chloro-2-propenyl) -oxy-imino] propyl ] -3-hydroxy-5- (tetra hydro-2H-pyran-4-yl) -2-cyclohexen-1-one (caloxydim, tepraloxydim), 2- (4-chloro-2-fluoro-5- (2- chloro-2-ethoxycarbonyl-ethyl) -phenyl) -4-difluoromethyl-5-methyl-2,4-di hydro-3H-1,2,4-triazol-3-one (Carfentrazone-ethyl), 2,4- Dichloro-1- (3-methoxy-4-nitro-phenoxy) benzene (chloromethoxyfen), 3-amino-2,5-dichloro-benzoic acid (chloro amben), N- (4-chloro-6-methoxy-pyrimidine- 2-yl) -N '- (2-ethoxycarbonylphenyl sulfonyl) urea (chlorimuron-ethyl), 1,3,5-trichloro-2- (4-nitro-phenoxy) benzene (chloronitrofen), N- ( 4-methoxy-6-methyl-1,3,5-triazi n-2-yl) -N '- (2-chlorophenyl sulfonyl) urea (chlorosulfuron), N' - (3-chloro-4-methyl - phenyl) -N, N-dimethyl urea (chlorotoluron), 2-chloro-3- [2-chloro-5- (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindole -2-yl) -phenyl] -2-propanoic acid ethyl ester (cinidon-ethyl), N- (4,6-dimethoxy-1,3,5-triazin-2-yl) -N '- (2- (2nd -methoxy-ethoxy) phenylsulfonyl) urea (cinosulfuron), 2- [1- [2- (4-chlorophenoxy) propoxyaminobutyl] -5- (tetrahydro-2H-thiopyran- 3-yl) -1, 3-cyclohexanedione (clefoxydim), (R) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) phenoxy propanoate (clodinafop propargyl), 3, 6-dichloropyridine-2-carboxylic acid (clopyralide), methyl-3-chloro-2 - [(5-ethoxy-7-fluoro [1, 2,4] triazolo [1,5-c] pyrimidin-2-yl -sulfonyl) -amino] -benzoate (chlorosulam-methyl), 2-chloro-4-ethylamino-6- (1-cyano-1-methyl-ethylamino) -1,3,5-triazine (cyanazines), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-cyclopropylcarbonylphenylsulfonyl) urea (cy closulfamuron), 2- (1-ethoximinobutyl) -3-hydroxy-5- (tetrahydro-2H -thiopyran-3-yl) - 2-cyclohexen-1-one (cycloxydim), (R) -2- [4- (4-cyano-2-fluorophenoxy) phenoxy] propane acid re-butyl ester (cyhalofop-butyl), 2,4-dichlorophenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxybenzoic acid (Dicamba), (R) -2- (2,4- Dichlorophenoxy) propanoic acid (dichloroprop-P), methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propanoate (diclofop-methyl), N- (2,6-dichlorophenyl) ) -5-ethoxy-7-fluoro- [1,2,4] triazolo- [1,5-c] pyrimidine-2-sulfonamide (diclosulam), 1,2-dimethyl-3,5-diphenyl-1H -pyrazolium methyl sulfate (difenzoquat), N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3-carboxamide (diflufenican), 2- [1 - [(3,5-difluoro -phenyl) -amino-carbonyl hydrazono] -ethyl] -pyridine-3-carboxylic acid (diflufenzopyr), S- (1-methyl-1-phenylethyl) -1-piperidine-carbothioate (dimepiperate), 2-chloro-N- (2,4-dimethyl-3-thienyl) - N- (2-methoxy-1-methyl-ethyl) -acetamide (dimethenamid), 2-amino-4- (1-fluoro-1-methyl-ethyl) -6 - (1-methyl-2- (3,5-dimethylphenoxy) ethylamino) -1,3,5-triazine (di mexyflam), N3, N3-diethyl-2,4-dinitro-6-trifluoromethyl-1 , 3-diamino-benzene (di nitramine), 6,7-dihydro-dipyrido [1,2-a: 2 ', 1'-c] pyra zindiium (diquat), S, S-dimethyl-2-difluoromethyl-4-i-butyl-6-trifluoromethyl-pyridine-3,5-dicarbothioate (dithiopyr), N'- (3,4-dichlorophenyl) -N , N-dimethyl-urea (diuron), 2- [2- (3-chlorophenyl) oxiranylmethyl] -2-ethyl-1H-indene-1,3 (2H) -dione (epropodane), S-ethyl- dipropylthio carbamate (EPTC), S- (phenylmethyl) -N-ethyl-N- (1,2-dimethyl-propyl) thiocarbamate (Esprocarb), N-ethyl-N- (2-methyl-2-propenyl) -2 , 6-dinitro-4-trifluoromethyl-benzene amine (ethalfluralin), (S) - (2-ethoxy-1-methyl-2-oxoethyl) -2-chloro-5- (2-chloro-4-tri fluoromethyl-phenoxy ) -benzoate (ethoxyfen), N- (4,6-dimethoxy-pyrimidin-2-yl) -N'- (2-ethoxy-phenoxysulfonyl) -urea (ethoxysulfuron), (R) -ethyl-2- [4- (6-chloro benzoxazol-2-yl-oxy) phenoxy] propanoate (fenoxaprop- (P) -ethyl), 4- (2-chlorophenyl) -N-cyclohexyl-N-ethyl-4,5-dihydro- 5-oxo-1H-tetrazole-1-carboxamide (Fen trazamid), isopropyl-N-benzoyl-N- (3-chloro-4-fluro-phenyl) -DL-alaninate (Flamprop isopropyl), isopropyl-N-benzoyl- N- (3-chloro-4-fluro-phenyl) -L-alaninate (Flamprop isopropyl-L) , Methyl-N-benzoyl-N- (3-chloro-4-fluoro-phenoxy) -DL-alaninate (Flam prop-methyl), N- (2,6-difluorophenyl) -8-fluoro-5-methoxy - [1,2,4] -triazolo- [1,5-c] - pyrimidine-2-sulfonamide (Florasulam), (R) -2- [4- (5-trifluoromethyl-pyridin-2-yl-oxy) - Butoxy phenoxy] propanoate (fluazifop, butyl, P-butyl), 5- (4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl) -2-chloro-4-fluoro -benzoic acid i-propyl ester (fluazolate), N- (4-fluorophenyl) -ni-propyl-2- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) acetamide (flufenacet ), N- (2,6-difluorophenyl) -5-methyl-1,2,4-triazolo [1,5-a] pyrimidine-2-sulfonamide (flumetsulam), pentyl- [2-chloro 4-fluoro-5- (1,3,4,5,6,7-hexa hydro-1,3-dioxo-2H-isoindol-2-yl) phenoxy] acetate (flumiclorac-pentyl), 2- [ 7-fluoro-3,4-dihydro-3-oxo-4- (2-propynyl) -2H-1,4-benzoxazin-6-yl] -4,5,6,7-tetrahydro-1H-isoindole-1 , 3-dione (flumioxazin), 2- [4-chloro-2-fluoro-5 - [(1-methyl-2-propynyl) -oxy] - phenyl] -4,5,6,7-tetrahydro-1H- isoindole-1,3 (2H) -dione (flumipropyn), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitr o-benzoic acid ethoxycarbonylmethyl ester (fluorogly cofen-ethyl), 1- (4-chloro-3- (2,2,3,3,3-pentafluoropropoxymethyl) phenyl) -5-phenyl-1H-1,2, 4-triazole-3-carboxamide (flupoxam), 1-isopropyl-2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidyl) - benzoate (flupropacil), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) -urea sodium salt (flupyrsulfuron-methyl- sodium), 9-hydroxy-9H-fluoren-9-carboxylic acid (flurenol), (4-amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) - acetic acid (-2-butoxy-1 -methyl-ethyl ester, -1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), 5-methylamino-2-phenyl-4- (3-trifluoromethyl-phenyl) -3 (2H) -furanone (flurtamone), Methyl - [(2-chloro-4-fluoro-5- (tetrahydro-3-oxo-1H, 3H- [1,3,4] thiadiazolo- [3,4-a] pyridazin-1-ylidene) - aminophenyl] thioacetate (Fluthiacet methyl), 5- (2-chloro-4-trifluoromethylphenoxy) -N-methylsulfonyl-2-nitro-benzamide (Fomesafen), 2-amino-4- (hydroxymethylphosphinyl) butanoic acid ( Ammonium salt) (glufosinate- (ammonium)), N-phosphonomethyl-glycine (-isopropylammmonium), (glyphosate, -isopropylammonium), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3- chloro-4-methoxycarbonyl-1-methyl-pyrazol-5-yl-sulfonyl) urea (halosulfuron methyl), (R) -2- [4- (3-chloro-5-trifluoromethyl-pyridin-2-yl-oxy ) -phenoxy] -propanoic acid (-methyl ester, -2-ethoxy-ethyl ester, -butyl ester) (haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 3-cyclohexyl-6-dimethylamino-1-methyl- 1,3,5-triazine-2,4- (1H, 3H) -dione (hexazinones), methyl-2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazole- 2-yl) -4-methyl-benzoate (imazamethabenz-methyl), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methyl- pyridine-3-carboxylic acid (Im azamethapyr), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid ( Imazamox), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -quinoline-3-carboxylic acid (imazaquine), 2- (4,5- Di hydro-4-methyl-4-i-propyl-5-oxo-1H-imidazo l-2-yl) -5-ethyl-pyridine-3-carboxylic acid (imazethapyr), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-chloro-imidazo [1,2- a] - pyridin-3-yl-sulfonyl) urea (imazosulfuron), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (5-iodo-2 -methoxycarbonyl-phenylsulfonyl) urea sodium salt (iodosulfuron-methyl-sodium), 4-hydroxy-3,5-diiodobenzonitrile (ioxynil), N, N-dimethyl-N '- (4-isopropyl-phenyl) - urea (isoproturon), N- (3- (1-ethyl-1-methylpropyl) isoxazol-5-yl) -2,6-dimethoxy-benzamide (isoxaben), (4-chloro-2-methyl sulfonyl- phenyl) - (5-cyclopropyl-isoxazol-4-yl) -methanone (isoxachlorotole), (5-cyclopropyl-isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethyl-phenyl) -methanone (isoxa flutole) , 2- [2- [4- [3,5-dichloro-2-pyridinyl) oxy] phenoxy] -1-oxo-propyl] isoxazolidine (isoxapyrifop), (2-ethoxy-1-methyl-2- oxo-ethyl) -5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoate (lactofen), N '- (3,4-dichloro-phenyl) -N-methoxy-N-methyl-urea (Linuron), (4-chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2 m ethyl-phenoxy) -propionic acid (mecoprop), 2- (2-benzothiazolyloxy) -N-methyl-N-phenyl-acetamide (Mefenacet), 2- (4-methylsulfonyl-2-nitrobenzoyl) -1,3-cyclohexanedione ( Mesotrione), 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5 (4H) -one (meta mitron), 2-chloro-N- (2,6-dimethyl-phenyl) - N- (1H-pyrazol-1-ylmethyl) acetamide (metazachlor), N '- (4- (3,4-dihydro-2-methoxy-2,4,4-trimethyl-2H-1-benzopyran 7- yl-oxy) -phenyl) -N-methoxy-N-methylurea (metobenzuron), N '- (4-bromophenyl) -N-methoxy-N-methylurea (metobromuron), (S) -2- Chloro-N- (2-ethyl-6-methyl-phenyl) -N- (2-methoxy-1-methyl-ethyl) -acet-amide (metolachlor, S-metola chlorine), N- (2,6-dichloro -3-methyl-phenyl) -5,7-dimethoxy-1,2,4-triazolo [1,5-a] pyrimidine-2-sulfonamide (metosulam), N '- (3-chloro-4-methoxy- phenyl) -N, N-dimethyl-urea (metoxuron), 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5 (4H) - one (metribuzin), N- ( 4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxy carbonyl-phenylsulfonyl) urea (metsulfuron-methyl), S-ethyl-hexahydro-1H- azepine-1-carbothioate (Molinate), 2- (2-naphthyloxy) -N-phenyl-propanamide (Napro anilide), N-butyl-N '- (3,4-dichlorophenyl) -N-methyl-urea ( Neburon), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl) urea (nicosulfuron), S- (2-chloro-benzyl ) -N, N-diethyl-thiocarbamate (Orbencarb), 4-di propylamino-3,5-dinitro-benzenesulfonamide (Oryzalin), 3- [2,4-dichloro-5- (2-propynyloxy) -phenyl] - 5- (t-butyl) -1,3,4-oxadiazol-2 (3H) -one (oxadiargyl), 3- [2,4-dichloro-5 - (1-methylethoxy) phenyl] -5- (t-butyl) -1,3,4-oxadiazol-2 (3H) -one (oxadiazon), N- (4,6-dimethyl-pyrimidin-2-yl) -N '- (2-oxetan-3- yl-oxycarbonyl-phenylsulfonyl) urea (oxasulfuron), 3- [1- (3,5-dichlorophenyl) -1-i-propyl] -2,3-dihydro-6-methyl-5-phenyl-4H -1,3-oxazin-4-one (oxaziclomefone), 2-chloro-1- (3-ethoxy-4-nitro-phen oxy) -4-trifluonomethylbenzene (oxyfluorfen), 1,1'-dimethyl-4 , 4'-bipyridinium (para quat), 1-amino-N- (1-ethyl-propyl) -3,4-dimethyl-2,6-dinitro-benzene (pendimethalin), 4- (t-butyl) -N - (1-ethyl-propyl) - 2,6-dinitro-benzenamine (pendralin), 4-amino-3,5,6-trichloropyridine-2-carboxylic acid (picloram), 2-chloro-N- (2,6-diethyl-phenyl) -N- (2-propoxy-ethyl) -acetamide (pretilachlor), N- (4-fluorophenyl) -6- (3-trifluoromethylphenoxy) -pyridine-2-carboxamide (picolinafen), N- (4,6-bis- difluoromethoxy-pyrimidin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (Primisulfuron methyl), 2-chloro-N-isopropyl-N-phenyl-acetamide (propachlor), N- (3,4 -Dichlorophenyl) -propanamide (propanil), 2-chloro-N- (2-ethyl-6-methyl-phenyl) -N - [(1-methylethoxy) -methyl] -acetamide (propisochlor), S-phenylmethyl- N, N-dipropylthiocarb amate (prosulfocarb), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2- (3,3,3-trifluoro propyl) phenylsulfonyl) urea (prosulfuron), ethyl- [2-chloro-5- (4-chloro-5-difluoro methoxy-1-methyl-1H-pyrazol-3-yl) -4-fluorophenoxy] - acetate (pyraflufen-ethyl), 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-5- (4-methylphenylsulfonyloxy) pyrazole (pyr azolate), 4- (2,4-dichloro- benzoyl) -1,3-dimethyl-5- (phenylcarbonylmethoxy) -p yrazole (pyrazoxyfen), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (4-ethoxycarbonyl-1-methyl pyrazol-5-yl-sulfonyl) urea (pyrazosulfuron-ethyl), diphenylmethanone O- [2,6- bis- (4,6-dimethoxypyrimidin-2-yloxy) benzoyl] oxime (pyribenzoxime), 6-chloro-3-phenyl-4-pyridazinol (pyridafole), O- (6-chloro-3-phenylpyridazin-4-yl) -S-octylthio carbonate (pyridate), 6-chloro-3-phenylpyridazin-4-ol (pyridatol), 2- (4,6-dimethoxy pyrimidin-2 -yl-oxy) -benzoic acid methyl ester (pyriminobac-methyl), 2-chloro-6- (4,6-dimethoxy-pyrimidin-2-ylthio) -benzoic acid sodium salt (pyrithiobac-sodium), 7-chloro-3- methyl quinoline-8-carboxylic acid (Quinmerac), 2- [4- (6-chloro-2-quinoxalinyl oxy) phenoxy] propanoic acid (ethyl ester, tetrahydro-2-furanyl methyl ester) (quizofop, ethyl) , -P-ethyl, -P-tefuryl), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-ethyl sulfonyl-pyridin-2-yl-sulfonyl) urea (rimsulfuron) , 2- (1-Ethoximinobutyl) -5- (2-ethylthiopropyl) -3-hydroxy-2-cyclohexen-1-one (Sethoxydim), 6-chloro-2,4-bis-ethylamino-1,3,5 -t riazine (simazine), 2- (2-chloro-4-methylsulfonylbenzoyl) cyclohexane-1,3-dione (sulcotrione), 2- (2,4-dichloro-5-methylsulfonylamino-phenyl) -4-difluoromethyl -5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (sulfentrazone), N-phosphonomethylglycine trimethylsulfonium (sulfosate), N- (4,6-dimethoxypyrimidine -2-yl) - N '- (2-ethylsulfonylimidazo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron), 6-chloro-4-ethylamino-2-tert-butylamino-1,3,5 -triazine (terbuthylazine), 2-tert-butylamino-4-ethylamino-6-methylthio-1,3,5-triazine (terbutryn), 2-chloro-N- (2,6-dimethylphenyl) -N- (3rd -methoxy-2-thienyl-methyl) -acetamide (thenylchlor), 2-difluoromethyl-5- (4,5-dihydro-thiazol-2-yl) -4- (2-methyl-propyl) -6-trifluoromethyl-pyridine -3-carbonic acid methyl ester (thiazopyr), 6- (6,7-dihydro-6,6-dimethyl-3H, 5H-pyrrolo [2,1-c] -1,2,4-thiadiazol-3-ylidenamino ) -7-fluoro-4- (2-propynyl) -2H-1,4-benzoxazin-3 (4H) -one (thidiazimin), N- (4-methoxy-6-methyl-1,3,5-triazine -2-yl) -N '- (2-methoxycarbonylthien-3-yl-sulfonyl) urea (thifensulfuron-me thyl), 2- (ethoximino-propyl) -3-hydroxy-5- (2,4,6-trimethyl-phenyl) -2-cyclohexen-1-one (tralkoxydim), S- (2,3,3-tri chloro-2-propenyl) diisopropyl carbamothioate (triallate), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- [2- (2-chloroethoxy) - phenylsulfonyl] urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonyl phenylsulfonyl) urea (tribenuron- methyl), (3,5,6-trichloro) pyridin-2-yl-oxyacetic acid (triclopyr), 2- (3,5-dichloro-phenyl) -2- (2,2,2-trichloroethyl) -oxirane (Tridi phane), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- (2,2,2-trifluoroethoxy) -2-pyridinesulfonamide sodium salt (trifloxysulfuron) , 1-Amino-2,6-dinitro-N, N-dipropyl-4-trifluoromethyl-benzene (trifluralin), N- [4-dimethylamino-6- (2,2,2-trifluoro-ethoxy) -1,3 , 5-triazin-2-yl] -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (triflusulfuron-methyl), N- (4-methoxy-6-trifluoromethoxy-1,3,5-triazin-2-yl ) -N '- (2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron), 2-pyridinesulfonam id, N- [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] -3- [methyl (methylsulfonyl) amino] (WO-A-92/10660), benzoic acid, 2 - [[[[( 4,6-Dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4 - [[(methylsulfonyl) amino] methyl], methyl ester (DE-A 43 35 297)
  ("Active substances of group 2"),
  and if necessary
• 3. at least one compound which improves the tolerance of crop plants from the following group of compounds:
  α- (1,3-dioxolan-2-yl-methoximino) phenylacetonitrile (oxabetrinil), α- (cyano methoximino) phenylacetonitrile (cyometrinil), 4-chloro-N- (1,3-dioxolan-2-yl- meth oxy) -α-trifluoro-acetophenone oxime (fluxofenim), 4,6-dichloro-2-phenylpyrimidine (fenclorim), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor) , 5-chloro-quinoxaline-8-oxyacetic acid (1-methyl-hexyl ester) (Cloquintocet), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) -ethyl) -N- (2-propenyl) acetamide (DKA-24), 1,8-naphthalic anhydride, 1- (2,4-dichlorophenyl) -5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester (Fenchlorazole-ethyl), 2-chloro-4-trifluoromethyl-thi azole-5-carboxylic acid phenylmethyl ester (Flurazole), 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyl-oxazolidine (Furilazole, MON- 13900), 4-dichloroacetyl-1-oxa-4-aza spiro [4.5] decane (AD-67), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2,2-dichloro -N- (1,3-dioxolan-2-yl-methyl) -N- (2-propenyl) -acetamide (PPG-1292), 2,2-di chloro-N, N-di-2-propenyl-acetamide (Dichlormid) , N- (4-Methyl-phenyl) -N '- (1-methyl-1-phenyl-ethyl) -urea (Dymron), 1-dichloroacetyl-hexahydro-3,3,8a-trimethyl pyrrolo [1,2- a] pyrimidine-6 (2H) -one (BAS-145138), N- (2-methoxy-benzoyl) -4- (methylaminocarbonylamino) -benzenesulfonamide, ethyl-4,5-dihydro-5,5-diphenyl-3 - isoxazole carboxylate (isoxadifen-ethyl), diethyl 1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl) and 2,4-dichlorophenoxy acetic acid (2,4-D) and its derivatives
  ("Active substances of group 3").

Preferred substituents of those shown in formula (I) shown above Leftovers are explained below.  

R ¹ preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine and / or chlorine.

R ² preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine and / or chlorine.

R ³ preferably represents hydrogen, fluorine, chlorine or bromine.

R ⁴ preferably represents cyano, thiocarbamoyl, fluorine, chlorine or bromine.

R ⁵ preferably represents nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hy droxy, mercapto, amino, hydroxyamino, aminosulfonyl, fluorine, chlorine, bromine, each optionally by cyano, hydroxy, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl and / or ethoxycarbonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t- Butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxy carbonyl, ethoxycarbonyl , n- or i-Propoxycarbonyl, methylamino, ethyl amino, n- or i-propylamino, n-, i-, s- or t-butylamino, for each optionally by cyano, carboxy, fluorine, chlorine, bromine, methoxycarbonyl and / or ethoxycarbonyl substituted ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy, for each optionally substituted by Fl uor and / or chlorine substituted acetyl amino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino, N, N-bis-methylsulfonylamino , N-bis-ethylsulfonyl-amino, N-ethylsulfonyl-N-methylsulfonyl-amino, N-acetyl-N-methylsulfonyl-amino, N-propionyl-N-methylsulfonyl-amino, Nn-butyroyl-N-methylsulfonyl-amino, Ni -Butyroyl-N-methylsulfonyl-amino, Ns-butyroyl-N-methylsulfonyl-amino, N-pivaloyl-N-methylsulfonyl-amino, N-acetyl-N-ethylsulfonyl-amino, N-propionyl-N-ethylsulfonyl-amino, Nn - Butyroyl-N-ethylsulfonyl-amino, Ni-butyroyl-N-ethylsulfonyl-amino, Ns-butyroyl-N-ethylsulfonyl-amino, N-pivaloyl-N-ethylsulfonyl-amino, or for each optionally by cyano, fluorine, chlorine, Bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted N-phenylcarbonyl-N-methylsulfonyl -amino, N-phenylcarbonyl-N-ethyl sulfonyl-amino, N-thienylcarbonyl-N-methylsulfonyl-amino or N-thienyl carbonyl-N-ethylsulfonyl-amino.

R ¹ particularly preferably represents methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine.

R ² particularly preferably represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine and / or chlorine.

R ³ particularly preferably represents hydrogen, fluorine or chlorine.

R ⁴ particularly preferably represents cyano or thiocarbamoyl.

R ⁵ particularly preferably represents nitro, cyano, carboxy, carbamoyl, thio carbamoyl, hydroxy, mercapto, amino, hydroxyamino, aminosulfonyl, fluorine, chlorine, bromine, each optionally by cyano, hydroxy, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl and / or ethoxy carbonyl substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl , n- or i-Butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i-propylamino, for each optionally substituted by cyano, carboxy, fluorine, chlorine, bromine, methoxycarbonyl and / or ethoxycarbonyl Ethenyl, propenyl, ethynyl, propynyl, propenyl oxy or propynyloxy for acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonylamino, ethylsulfonylamino, each optionally substituted by fluorine and / or chlorine , n- or i-Propylsulfonylamino, N, N-bis-methylsulfonyl-amino, N, N-Bis-ethyl sulfonyl-amino, N-ethylsulfonyl-N-methylsulfonyl-amino, N-acetyl-N-methylsulfonyl-amino, N -Propionyl-N-methylsulfonyl-amino, Nn-butyroyl-N-methylsulfonyl-amino, Ni-butyroyl-N-methylsulfonyl-amino, Ns-butyroyl-N-methylsulfonyl-amino, N-pivaloyl-N-methylsulfonyl-amino, N - Acetyl-N-ethylsulfonyl-amino, N-propionyl-N-ethylsulfonyl-amino, Nn-butyroyl-N-ethylsulfonyl-amino, Ni-butyroyl-N-ethylsulfonyl-amino, Ns-butyroyl-N-ethylsulfonyl-amino, N -Pivaloyl-N-ethylsulfonyl-amino, or for each substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy sub-substituted N-phenylcarbonyl-N-methylsulfonyl-amino, N-phenylcarbonyl -N-ethylsulfonyl-amino, N-thienylcarbonyl-N-methylsulfonyl-amino or N-thienylcarbonyl-N-ethylsulfonyl-amino.

Examples of the compounds of the formula (I) to be used as mixture partners according to the invention are:
2- (4-Cyano-2-fluoro-5-methylsulfonylaminophenyl) -4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4th -Cyano-2-fluoro-5-ethylsulfonylamino-phenyl) -4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-cyano-2 -fluoro-5-methylsulfonylamino-phenyl) -4-methyl-5-difluoromethyl-2,4-dihydro-3H-1,2,4-tri azol-3-one, 2- (4-cyano-2-fluoro- 5-ethylsulfonylamino-phenyl) -4-methyl-5-difluoro methyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-cyano-2-fluoro-5-methylsulfonyl aminophenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-cyano-2-fluoro-5-ethylsulfonylamino-phenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-cyano-2-fluoro-5-methylsulfonylamino-phenyl) -4-ethyl -5-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-cyano-2-fluoro-5-ethyl sulfonylaminophenyl) -4-ethyl-5- difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-thiocarbamoyl-2-fluoro-5-methylsulfonylaminophenyl) -4-methyl-5-trifluoromethyl-2 , 4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-thiocarbamoyl-2-fluoro-5-ethyl sulfonylamino-phenyl) -4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4- Thiocarbamoyl-2-fluoro-5-methylsulfonylamino-phenyl) -4-methyl-5-difluoro methyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-thiocarbamoyl-2 -fluoro-5-ethyl sulfonylamino-phenyl) -4-methyl-5-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-thiocarbamoyl-2-fluoro- 5-methylsulfonylaminophenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-thiocarbamoyl-2-fluoro-5-ethyl sulfonylamino-phenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-thiocarbamoyl-2-fluoro-5-methylsulfonylamino-phenyl) -4-ethyl-5-difluoro methyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-thiocarbamoyl-2-fluoro-5-ethyl sulfonylamino-phenyl) -4 -ethyl-5-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one.

The compound 2- (4-thiocarbamoyl-2-fluoro-5-ethylsulfonylamino-phenyl) -4-me thyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one (I-1) - according to Chem. Abstracts also as 4- [4,5-dihydro-4-methyl-5-oxo (3-trifluoromethyl) -1H-1,2,4-triazol-1-yl] -2- To designate [(ethylsulfonyl) amino] -5-fluoro-benzenecarbothioamide (CAS Reg.-No .: 173980-17-1) - is particularly prominent as a mixture component of formula (I) raised.

The compounds 2- (4-cyano-2-fluoro-5-ethylsulfonylamino-phenyl) -4-methyl-5-tri fluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one (I-2) - according to Chem. Abstracts also as N- [2-cyano-5- [4,5-dihydro-4-methyl-5-oxo-3-trifluoromethyl-1H-1,2,4-triazol-1-yl] - To designate 4-fluoro-phenyl] -ethanesulfonamide (CAS Reg.No .: 157739-55-4) - and 2- (4-cyano-2-fluoro-5-ethylsulfonylaminophenyl) -4-ethyl-5-trifluoromethyl-2,4-di hydro-3H-1,2,4-triazol-3-one (I-3) - according to Chem. Abstracts also as N- [2-cyano-5- [4- ethyl-4,5-dihydro-5-oxo-3-trifluoromethyl-1H-1,2,4-triazol-1-yl] -4-fluorophenyl] - to designate ethanesulfonamide (CAS Reg.No .: 157739-37-2) - and 2- (4-cyano-2- fluoro-5-methylsulfonylamino-phenyl) -4-methyl-5-difluoromethyl-2,4-dihydro-3H- 1,2,4-triazol-3-one (I-4) - according to Chem. Abstracts also as N- [2-cyano-5- [3-difluoro  methyl-4,5-dihydro-4-methyl-5-thioxo-1H-1,2,4-triazol-1-yl] -4-fluorophenyl] - to designate methanesulfonamide (CAS Reg.No .: 157739-46-3) - are further referred to as possible mixture components of formula (I) are particularly highlighted.

The compounds of formula (I) are in the above to the N-aryl triazolin (thi) onen specified patent applications or patents.

The active substances of group 2 can be assigned to their chemical structure according to the following active substance classes:
Amides (e.g. Isoxaben, Propanil), aryl heterocycles (e.g. Azafenidin, Carfentrazone ethyl, Cinidon-ethyl, Fluazolate, Flumiclorac-pentyl, Flumioxazin, Fluthiacet methyl, Oxadiazon, Oxadiargyl, Pyraflufen-ethyl, Pyridentra, Pyridafol, Sulfid , Thidiazimin), aryloxyphenoxypropionates (e.g. clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-R-methyl, quizalofop-P-ethyl), carboxylic acid derivatives (e.g. B. clopyralid, dicamba, fluroxypyr, picloram, triclopyr), benzothiadiazoles (e.g. bentazone), chloroacetamides (e.g. acetochlor, alachlor, butachlor, dimethenamid, metazachlor, metolachlor, pretilachlor, propachlor, propisochione (z B. Butroxydim, Clef oxydim, Cycloxydim, Sethoxydim, Tralkoxydim), Dinitroaniline (e.g. Benfluralin, Ethalfluralin, Oryzalin, Pendimethalin, Trifluralin), Diphenylether (e.g. Acifluorfen sodium, Aclonifen, Bifen-ethyl, Fluoroglyofenofen , Lactofen, oxyfluor fen), ureas (e.g. Chlo rtoluron, diuron, isoproturon, linuron, metobromuron, metoxuron), imidazolinones (e.g. B. Imazamethabenz-methyl, Imazamox, Imazaquin, Imazethapyr), Isoxazole (e.g. Isoxaflutole), Nicotinanilide (e.g. Diflufenican), Nitrile (e.g. Bromoxynil, Ioxynil), Organophosphorus compounds (e.g. Glufosinates, glyphosates, sulfosates), oxyacetamides (e.g. flufenacet, mefenacet), phenoxycarbonic acid derivatives (e.g. 2,4-D, dichloroprop, MCPA, MCPB, mecoprop), pyrazoles (e.g. pyrazolates, pyrazoxyfen) , Pyridines (e.g. dithiopyr, thiazopyr), pyrimidinyl (thio) benzoates (e.g. bispyribac, pyribenzoxime, pyrithiobac, pyriminobac), sulfonylureas (e.g. amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl , chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flupyrsulfuron-methyl-sodium, halosulfuron-methyl, imazosulfuron, metsulfuron-methyl, Nico Sulfuron, oxasulfuron, Primisulfuronmethyl, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfosulfuron, thifensulfuron-methyl, triasulfuron, Tribenuron- methyl, triflusulfuron-methyl), tetrazolinones (e.g. fentrazamide ), Thiocarbamates (e.g. B. Butylates, Dimepiperate, EPTC, Esprocarb, Molinate, Orbencarb, Prosulfocarb, Triallate), Triazole (e.g. Amitrole), Triazolopyrimidine (e.g. Cloransulam-methyl, Diclosulam, Florasulam, Flumetsulam, Metosulam), Triazine (e.g. B. Ametryn, Atrazin, Cyanazine, Simazin, Terbuthylazine, Terbutryn), Triazinone (e.g. Hexazinone, Metamitron, Metribuzin), Triketone (e.g. Mesotrione, Sulcotrione).

The following are particularly emphasized as mixture components from the active ingredients of group 2:
Atrazine, bromoxynil, chlorimuron-ethyl, clodinafop-propargyl, dicamba, dichloroprop-P, diflufenican, dimethenamid, fenoxaprop- (P) -ethyl, fentrazamide, flufen acet, flupyrsulfuron-methyl-sodium, flurtamone, glufosinate-ammonium, glyphosate isopropylammonium, imazamethapyr, imazamox, iodosulfuron-methyl sodium, mesotrione, metolachlor, metosulam, metribuzin, metsulfuron-methyl, nicosulfuron, rimsulfuron, sulcotrione, sulfosate, sulfosulfuron, terbuthylazine, methyl, trifulfuroxuron.

The active substances in Group 2 that are particularly highlighted can be assigned to their chemical structure according to the following classes of active substances:
Aryloxyphenoxypropionates (e.g. clodinafop-propargyl, fenoxaprop-P-ethyl), carboxylic acid derivatives (e.g. dicamba, fluroxypyr), chloroacetamides (e.g. dimethene amide, metolachlor), cyclohexanediones (e.g. tralkoxydim), ureas (e.g. isoprot uron), imidazolinones (e.g. imazamethabenz-methyl, imazamox), nicotinanilides (e.g. diflufenican), nitriles (e.g. bromoxynil), organophosphorus compounds (e.g. glufosinate, Glyphosates, sulfosates), oxyacetamides (e.g. Flufenacet), phenoxy carboxylic acid derivatives (e.g. dichlorprop-P), sulfonylureas (e.g. chlorimuron ethyl, flupyrsulfuron-methyl-sodium, metsulfuron-methyl, nicosulfuron, sulfosulfuron, Thifensulfuron-methyl, tribenuron-methyl), triazolopyrimidines (e.g. florasulam, metosulam), triazines (e.g. ametryn, atrazine, terbuthylazine), triazinones (e.g. metribuzin), triketones (e.g. mesotrione, Sulcotrione).

The agents according to the invention preferably contain one to three active ingredients of Group 2.

Mixtures comprising compound I-1, tritosulfuron and a compound from the following group of compounds are particularly emphasized:
4-Amino-N- (1,1-dimethyl-ethyl) -4,5-dihydro-3- (1-methyl-ethyl) -5-oxo-1H-1,2,4-tri azole-1-carboxamide (Amicarbazone), N-benzyl-2- (4-fluoro-3-trifluoromethyl-phenoxy) butanamide (Beflubutamide), 2,6-bis (4,6-dimethoxy-pyrimidin-2-yl-oxy) benzo acid sodium salt (bispyribac-sodium), (R) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) -phenoxy-propanoate (clodinafop-propargyl), 2,4-dichlorophenoxy acetic acid (2,4-D), 3,6-dichloro-2-methoxy-benzoic acid (Dicamba), (R) -2- (2,4-di chlorophenoxy) propanoic acid (dichloroprop) P), N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3-carboxamide (diflufenican), 2- [1 - [(3,5-difluorophenyl) - amino-carbonyl-hydrazono] -ethyl] pyridine-3-carboxylic acid (diflufenzopyr), (S-) 2-chloro-N- (2,4-dimethyl-3-thienyl) -N- (2-methoxy-1 -methyl-ethyl) -acetamide (S-) (di methenamid), (R) -ethyl-2- [4- (6-chloro-benzoxazol-2-yl-oxy) -phenoxy] -propanoate (fenoxaprop- (P ) -ethyl), 4,5-dihydro-3-methoxy-4-methyl-5-oxo-N - [(2-trifluoromethoxyphenyl) sulfonyl] -1-H-1,2,4-triazole- 1- carboxamide sodium salt (Flucarbazone sodium), N- (4-fluorophenyl) -Ni-propyl-2- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl oxy) -acetamide (Flufenacet), N- (4,6-Dimethoxy-pyrimidin-2-yl) -N '- (3-methoxy carbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (flupyrsulfuron-methyl-sodium), 2- [[[[((4,6-Dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4-formylamino-N, N-dimethyl-benzamide (foramsulfuron), 2-amino-4- ( hydroxymethylphosphinyl) butanoic acid (ammonium salt) (glufosinate (ammonium)), N-phosphonomethylglycine (isopropylammmonium salt), (glyphosate, isopropylammonium), 2- (4,5-dihydro-4-methyl-4-isopropyl -5-oxo-1H-imidazol-2-yl) -5-methoxymethyl-pyridine-3-carboxylic acid (imazamox), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonyl-phenylsulfonyl) urea sodium salt (iodosulfuron-methyl-sodium), N, N-dimethyl-N' - (4-isopropyl phenyl) urea (isoproturon), ( 4-chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid acid (mecoprop), 2- (4-methylsulfonyl-2-nitrobenzoyl) -1,3-cyclohexanedione (mesotrione), 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5 (4H) -one (metribuzin), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-dimethylcarbamoyl-pyridin-2-yl-sulfonyl) urea (nicosulfuron), 2- [[[((4,5-Dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl) carbonyl] amino] sulfonyl] methyl benzoate - Sodium salt (propoxycarbazone-sodium), 2- (1-ethoximinobutyl) -5- (2-ethylthiopropyl) -3-hydroxy-2-cyclohexen-1-one (sethoxydim), N-phosphonomethylglycine trimethylsulfonium (sulfosate), N- (4,6-Dimethoxypyrimin-2-yl) -N '- (2-ethylsulfonylimidazo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron), 2- (ethoximinopropyl) - 3-hydroxy-5- (2,4,6-trimethyl-phenyl) -2-cyclohexen-1-one (Tral koxydim), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl ] -3- (2,2,2-trifluoroethoxy) -2-pyridinesulfonamide sodium salt (trifloxysulfuron).

Mixtures comprising compound I-1, picolinafen and a compound from the following group of compounds are also emphasized:
2,6-bis- (4,6-dimethoxypyrimidin-2-yl-oxy) -benzoic acid sodium salt (bispyribac sodium), (R) - (2-propynyl) -2- [4- (5-chloro- 3-fluoro-pyridin-2-yl-oxy) phenoxy-pro panoat (Clodinafop-propargyl), 2-chloro-4-ethylamino-6- (1-cyano-1-methyl-ethyl amino) -1,3, 5-triazine (cyanazines), 2,4-dichlorophenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxybenzoic acid (Dicamba), (R) -2- (2,4-dichloro -phenoxy) -propanoic acid (dichloroprop-P), (R) -ethyl-2- [4- (6-chloro-benzoxazol-2-yl-oxy) -phenoxy] -propanoate (fenoxaprop- (P) -ethyl), 4,5-Dihydro-3-methoxy-4-methyl-5-oxo-N - [(2-trifluoromethoxyphenyl) sulfonyl] -1-H-1,2,4-triazole-1-carboxamide sodium salt (Flucarbazone sodium), N- (4-fluorophenyl) -Ni-propyl-2- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl oxy) -acetamide (Flufenacet), N- (4, 6-Dimethoxy-pyrimidin-2-yl) -N '- (3-methoxy carbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea sodium salt (flupyrsulfuron-methyl-sodium), N- (4- Methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (5-iodo-2-methoxycarbonyl-phenylsulfonyl) urea sodium Malt (iodosulfuron-methyl sodium), N, N-dimethyl-N '- (4-isopropylphenyl) urea (isoproturon), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), N - (2,6-dichloro-3-methylphenyl) -5,7-dimethoxy-1,2,4-triazolo [1,5-a] pyrimidine-2-sulfonamide (metosulam), 4-amino-6 - tert-butyl-3-methylthio-1,2,4-triazin-5 (4H) -one (metribuzin), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (Met sulfuron-methyl), 2 - [[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2, 4-triazol-1-yl) -carbonyl] -amino] -sulfonyl] -benzoic acid methyl ester sodium salt (propoxycarb azone-sodium), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- ( 2-ethylsulfonyl-imidazo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) - N '- (2nd -methoxycarbonyl-thien-3-yl-sulfonyl) -urea (thifensulfuron-methyl), N-methyl-N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N'- (2-methoxycarbonylphenyl sulfonyl) urea (tribenuron methyl), N - [[(4,6-dimethoxy-2-pyrimidinyl) amino] carbo nyl] -3- (2,2,2-trifluoro-ethoxy) -2-pyridinesulfonamide sodium salt (tri-floxysulfuron), N- (4-methoxy-6-trifluoromethoxy-1,3,5-triazin-2-yl) -N '- (2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron).

It has now surprisingly been found that the active ingredient defined above combinations of the N-aryl-triazolin (thi) ones of the formula (I) and the above Active ingredients listed in group 2 with very good crop tolerance have a particularly high herbicidal activity and in different Cultures, especially in barley, corn, rice and wheat, for selective weed plants fighting can be used.

Surprisingly, the herbicidal activity of the active compound according to the invention Combinations of substances from compounds of groups 1 and 2 listed above Lich higher than the sum of the effects of the individual active ingredients.  

There is therefore an unforeseeable synergistic effect and not just one Addition of effects. The new drug combinations are good in many cultures tolerated, although the new active ingredient combinations are difficult to combat combat weeds well. The new active ingredient combinations thus represent one valuable enrichment of selective herbicides.

The synergistic effect of the active compound combinations according to the invention is in be certain concentration ratios are particularly pronounced. However, can the weight ratios of the active ingredients in the active ingredient combinations in relative large areas can be varied. In general, 1 part by weight of active ingredient is used substance of formula (I) 0.01 to 1000 parts by weight, preferably 0.02 to 500 Ge parts by weight and particularly preferably 0.05 to 100 parts by weight of active ingredient Group 2.

The following are particularly emphasized as mixture components from the active ingredients of group 3:
5-chloro-quinoxaline-8-oxyacetic acid (1-methylhexyl ester) (cloquintocet), 1- (2,4-di chlorophenyl) -5-trichloromethyl-1H-1,2,4-triazole-3- carboxylic acid ethyl ester (fenchlor azole-ethyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), diethyl-1- (2,4-dichlorophenyl) -4,5-dihydro -5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives.

It was surprisingly found that the active substance combinations defined above from N-aryl-triazolin (thi) ones of the formula (I) or their salts and one Safener / antidote ("active substances of group 3") in combination with one or more of the above-mentioned active ingredients of group 2 with very good crop tolerance have a particularly high herbicidal activity and in different Cultures, especially in barley, corn, rice and wheat, for selective weed crops fighting can be used.  

Surprisingly, it was also found that the herbicidal Substance 2,4-dichlorophenoxyacetic acid (2,4-D) and its derivatives be the above can take over the written safener task.

A preferred embodiment is therefore also a mixture containing one Compound of formula (I) and / or its salts on the one hand and 2,4-D and / or its Derivatives, on the other hand, optionally in combination with one or more of the Active ingredients of group 2 mentioned above. Typical derivatives of 2,4-D are e.g. B. their esters.

The compounds diethyl-1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole- 3,5-dicarboxylates (mefenpyr-diethyl), (1-methylhexyl) - [(5-chloro-8-quinolinyl) oxy] - acetate (Cloquintocet-mexyl) and ethyl 1- (2,4-dichlorophenyl) -5- (trichloromethyl) - 1H-1,2,4-triazole-3-carboxylates (fenchlorazole-ethyl) are described in the following patents described: DE-A-39 39 503, EP-A-191 736 and DE-A-35 25 205. 2,4-D is a well-known herbicide.

It is surprising that a large number of known Safeners or antidotes that are capable of the harmful effects of a herbicide to antagonize the crops, just the active ingredients listed above Group 3 are suitable, the damaging effect of compounds of formula (I) and their salts, optionally also in combination with one or more of the Active ingredients of group 2 mentioned above, almost fully on the crop plants constantly cancel, without the herbicidal activity against the Un to affect herbs.

The particularly advantageous effect of the especially before should be emphasized here combination partners from group 3, especially with regard to the Protection of cereal plants, such as. B. wheat, barley and rye.  

The advantageous effect of crop tolerance of the active compound according to the invention combinations of substances is also special at certain concentration ratios very pronounced. However, the weight ratios of the active ingredients in the Drug combinations can be varied in relatively large areas. In general account for 1 part by weight of active ingredient of the formula (I), its salts or its Mixtures with active ingredients of group 2 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight and particularly preferably 0.1 to 10 parts by weight of one of the Above under (c), the crop plant tolerance improving Ver bindings (antidots / safeners).

According to the invention, all plants and parts of plants can be treated. Under Plants are understood here as all plants and plant populations desired and undesirable wild plants or crops (including natural cultivated plants). Cultivated plants can be plants that are caused by conventional breeding and optimization methods or by biotechnological and obtained genetic engineering methods or combinations of these methods can be, including the transgenic plants and including by Plant variety rights of protectable or non-protectable plant varieties. Under Plant parts should include all above-ground and underground plant parts and organs the plants, such as sprout, leaf, flower and root are understood, with playful leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhiozomes. To the plant parts ge also hears vegetative and generative propagation material, for example Cuttings, tubers, rhizomes, offshoots and seeds.

The treatment according to the invention of the plants and parts of plants with the active ingredients substances takes place directly or by influencing their surroundings, living space or Storage room according to the usual treatment methods, e.g. B. by diving, spraying, Evaporation, misting, scattering, spreading and in the case of propagation material, in particular in the case of seeds in particular, by wrapping them in one or more layers.  

Among those through biotechnological and genetic engineering methods or through Plants obtained by combining these methods will produce such plants elevated, tolerate the so-called 4-HPPD, EPSP and / or PPO ureas, such as. B. Acuron plants.

The active compound combinations according to the invention can, for. B. used in the following plants:
Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cuburbita.
Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Iochasumirumum, Scalumumum, Scalumumum , Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Phalaris.
Monocot cultures of the genera: Oryza, Zea, Triticurn, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

However, the use of the active compound combinations according to the invention is not one wegs limited to these genera, but extends in the same way other plants.  

The active substance combinations can be converted into the usual formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts medium, pastes, soluble powders, granules, suspension emulsion concentrates, Active ingredient-impregnated natural and synthetic substances as well as very fine encapsulation in polymeric fabrics.

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients with extenders, i.e. liquid solvents and / or solid Carriers, optionally using surface-active agents, thus emulsifiers and / or dispersants and / or foam-producing Means.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkylnaph thalines, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. 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 and dimethyl sulfoxide, and water.

The following are suitable as solid carriers:
e.g. B. ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: z. B. stem and fractionate natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco; as emulsifying and / or foam-generating agents come into question: z. B. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersants come into question: z. B. lignin sulfite and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural, can be used in the formulations and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho lipids such as cephalins and lecithins and synthetic phospholipids. Further Additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan 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 can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active ingredients, preferably between 0.5 and 90%.

The active compound combinations according to the invention are generally in the form of ready formulations applied. The in the active ingredient Combinations of active ingredients can also be used in individual formulations mixed the application, d. H. in the form of tank mixes for use be brought.

The new drug combinations can be used as such or in their formulations continue to be used in a mixture with other known herbicides, ready formulations or tank mixes are possible. Also a mixture with other known active ingredients, such as fungicides, insecticides, Acaricides, nematicides, bird repellants, growth agents, plants  nutrients and soil structure improvers are possible. For certain types purposes, especially in the post-emergence process, it can also be advantageous be plant-compatible in the formulations as further additives mineral or vegetable oils (e.g. the commercial preparation "Oleo DuPont 11E") or ammonium salts such as e.g. B. ammonium sulfate or ammonium rhodanide to take.

The new active substance combinations 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 be applied. The application is done in the usual way, e.g. B. by pouring, Spraying, spraying, dusting or sprinkling.

The active compound combinations according to the invention can be used before and after run of the plants are applied, i.e. in the pre-emergence and post-emergence ver drive. They can also be worked into the soil before sowing.

The good herbicidal activity of the new combinations of active ingredients follows from the following examples. While the individual active ingredients in the herbicidal The combinations show a very good effect Weed action that goes beyond a simple addition of effects.

A herbicide always has a synergistic effect if the herbicide Effect of the active ingredient combination is greater than that of the individual applied Active ingredients.

The expected effect for a given combination of two herbicides can can be calculated as follows (cf. COLBY, S. R .: "Calculating synergistic and antagonistic responses of herbicide combinations ", Weeds 15, pages 20-22, 1967):

If
X =% damage by herbicide A (active ingredient of the formula I) at a rate of p kg / ha
and
Y =% damage by herbicide B (active ingredient of the formula II) at q kg / ha application rate
and
E = the expected damage to herbicides A and B at p and q kg / ha application rate,
then
E = X + Y - (XY / 100).

If the actual damage is greater than calculated, the combination is in its Effect superadditive, that is, it shows a synergistic effect.

Claims (9)

1. Agent, characterized by an effective content of an active ingredient combination comprising

• 1. at least one N-aryl-triazolin (thi) on of the general formula (I)
  in which
  Q ^{1 represents} oxygen or sulfur,
  R ^{1 represents} alkyl which has 1 to 5 carbon atoms and is optionally substituted by halogen,
  R ^{2 represents} alkyl which has 1 to 5 carbon atoms and is optionally substituted by halogen,
  R ^{3 represents} hydrogen or halogen,
  R ^{4 represents} cyano, thiocarbamoyl or halogen, and
  R ⁵ for nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, hydroxyamino, aminosulfonyl, halogen, for each case optionally by cyano, hydroxy, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl carbonyl and / or C ₁ -C ₄ alkoxy-carbonyl substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl or alkylamino each having 1 to 6 carbon atoms, each optionally with cyano, carboxy, halogen and / or C ₁ -C ₄ -alkoxy-carbonyl-substituted alkenyl, alkynyl, alkenyloxy or alkynyloxy each having 2 to 6 carbon atoms, for each optionally substituted by halogen-substituted alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, N, N-bis alkylsulfonylamino or N-alkylcarbonyl-N alkylsulfonylamino each having 1 to 6 carbon atoms in the alkyl groups, or for each case optionally by cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy substi tuier tes N-phenylcarbonyl-N-alkylsulfonyl-amino, N-pyridylcarbonyl-N-alkylsulfonyl-amino, N-furylcarbonyl-N-alkylsulfonyl-amino or N-thienylcarbonyl-N-alkylsulfonyl-amino, each with 1 to 6 carbon atoms in the Alkyl groups,
  ("Active substances of group 1")
  and
• 2. at least one compound from a second group of herbicides which contains the active compounds mentioned below:
  2-chloro-N- (ethoxymethyl) -N- (2-ethyl-6-methyl-phenyl) -acetamide (aceto chlorine), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid- Sodium salt (acifluorosodium), 2-chloro-6-nitro-3-phenoxy-benzenamine (Aclonifen), 2-chloro-N- (methoxymethyl) -N- (2,6-diethyl-phenyl) -acetamide (alachlor), N-ethyl-N'-i-propyl-6-methylthio-1,3,5-triazine-2,4-diamine (ametryn), N- (4,6-dimethoxypyrimidin-2-yl) -N ' - (N-methyl-N-methyl sulfonylsulfamoyl) urea (amidosulfuron), 1H-1,2,4-triazol-3-amine (amitrole), 6-chloro-4-ethylamino-2-isopropylamino-1, 3,5-triazine (atrazine), N- (4,6-dimethoxypyrimidin-2-yl) -N '- [1-methyl-4- (2-methyl-2H-tetrazol-5-yl) -1H -pyrazol-5-ylsulfonyl] urea (azimsulfuron), 2- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5,6,7,8-tetrahydro-1,2,4-triazolo - [4,3-a] -pyridin-3 (2H) - one (azafenidin), N-benzyl-2- (4-fluoro-3-trifluoromethyl-phenoxy) -butanamide (beflubutamide), 4-chloro-2- oxo-3 (2H) -benzthiazole acetic acid (benazoline), N-butyl-N-ethyl-2,6-dinitro-4-trifluoromethyl-benzenamine (benfluralin ), N- (4,6-Dimethoxypyrimidin-2-yl) -N '- (2-methoxycarbonylphenylmethylsulfonyl) urea (bensulfuron), 2- [2- [4- (3,6-dihydro-3 -methyl-2,6-dioxo-4-trifluoromethyl-1 (2H) -pyrimidinylphenoxymethyl] -5-ethyl-phenoxy-propanoic acid methyl ester (benzfendizone), 3- (2-chloro-4-methylsulfonyl-benzoyl) -4- phenylthio-bicyclo- [3.2.1] oct-3-en-2-one (benzobicyclone), ethyl-N-benzoyl-N- (3,4-dichlorophenyl) -DL-alaninate (benzoylprop-ethyl), 3-i-propyl-1H-2,1,3-benzothiadiazin-4 (3H) -one (bentazone), methyl 5- (2,4-dichlorophenoxy) -2-nitro-benzoate (bifenox), 2 , 6-bis- (4,6-dimethoxy-pyrimidin-2-yl-oxy) benzoic acid sodium salt (bispyribac-sodium), 2-bromo-3,3-dimethyl-N- (1-methyl-1-phenyl -ethyl) -butanamide (bromobutide), 3,5-dibromo-4-hydroxybenzaldehyde-O- (2,4-dinitro-phenyl) -oxime (bromofenoxime), 3,5-dibromo-4-hydroxybenzonitrile (bromoxynil ), N-Butoxymethyl-2-chloro-N- (2,6-diethylphenyl) -acetamide (butachlor), 2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4 - trifluoromethyl-1 (2H) -pyrimidinyl) -benzoic acid- [1,1-di methyl-2-oxo-2- (2-propenyloxy)] ethyl ester (butafenacil-allyl), 2- (1-ethoximino-propyl) -3-hydroxy-5- [2,4,6-trimethyl-3- ( 1-oxo-butyl) phenyl] -2-cyclohexen-1-one (butoxydim), S-ethyl-bis- (2-methyl-propyl) -thiocarbamate (butylate), N, N-diethyl-3- ( 2,4,6-trimethyl-phenylsulfonyl) -1H-1,2,4-triazole-1-carboxamide (cafenstrole), 2- [1 - [(3-chloro-2-propenyl) -oxy-imino] propyl ] -3-hydroxy-5- (tetrahydro-2H-pyran-4-yl) -2-cyclohexen-1-one (caloxydim, tepraloxydim), 2- (4-chloro-2-fluoro-5- (2-chloro -2-ethoxycarbonyl-ethyl) -phenyl) -4-difluoro methyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (carfentrazone-ethyl), 2,4-dichloro -1- (3-methoxy-4-nitro-phenoxy) benzene (chloromethoxyfen), 3-amino-2,5-dichlorobenzoic acid (chlorambene), N- (4-chloro-6-methoxy-pyrimidine-2 -yl) -N '- (2-ethoxycarbonyl-phenylsulfonyl) urea (chlorimuron ethyl), 1,3,5-trichloro-2- (4-nitro-phenoxy) benzene (chloronitrofen), N- (4-methoxy -6-methyl-1,3,5-triazin-2-yl) -N '- (2-chlorophenylsulfonyl) urea (chlorosulfuron), N' - (3-chloro-4-methyl- phenyl) -N, N-dimethyl-urea (chlorotoluron), 2-chloro-3- [2-chloro-5- (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H- isoindol-2-yl) -phenyl] -2-propanoic acid ethyl ester (cinidon-ethyl), N- (4,6-dimethoxy-1,3,5-triazin-2-yl) -N '- (2- ( 2-methoxyethoxy) phenylsulfonyl) urea (cinosulfuron), 2- [1- [2- (4-chlorophenoxy) propoxyaminobutyl] -5- (tetrahydro-2H-thiopyran-3-yl) -1, 3-cyclohexanedione (clefoxydim), (R) - (2-propynyl) -2- [4- (5-chloro-3-fluoropyridin-2-yl-oxy) phenoxy propanoate (Clo dinafop propargyl), 3,6-dichloropyridine-2-carboxylic acid (clopyralide), methyl 3-chloro-2 - [(5-ethoxy-7-fluoro [1,2,4] triazolo [1,5-c] pyrimidine-2 -yl-sulfonyl) - amino] benzoate (chlorosulam-methyl), 2-chloro-4-ethylamino-6- (1-cyano-1-methyl-ethylamino) -1,3,5-triazine (cyanazine), N - (4,6-Dimethoxypyrimidin-2-yl) -N '- (2-cyclopropylcarbonylphenylsulfonyl) urea (Cyclosulfa muron), 2- (1-ethoximinobutyl) -3-hydroxy-5- (tetrahydro-2H -thiopyran-3-yl) - 2-cyclohexen-1-one (cycloxydim), (R) -2- [4- (4-cyano-2-fluorophenoxy) phenoxy] propane ure-butyl ester (cyhalofop-butyl), 2,4-dichlorophenoxyacetic acid (2,4-D), 3,6-dichloro-2-methoxybenzoic acid (Dicamba), (R) -2- (2,4 -Di chlorophenoxy) propanoic acid (dichloroprop-P), methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propanoate (diclofop-methyl), N- (2,6-dichlorophenyl) ) -5-ethoxy-7-fluoro- [1,2,4] triazolo- [1,5-c] pyrimidine-2-sulfonamide (diclosulam), 1,2-dimethyl-3,5-diphenyl-1H -pyrazolium methyl sulfate (difenzoquat), N- (2,4-difluorophenyl) -2- (3-trifluoromethylphenoxy) pyridine-3-carboxamide (di flufenican), 2- [1 - [(3.5 -Difluoro-phenyl) -amino-carbonyl-hydrazono] -ethyl] - pyridine-3-carboxylic acid (diflufenzopyr), S- (1-methyl-1-phenyl-ethyl) -1-piperidine-carbothioate (dimepiperate), 2 -Chlor-N- (2,4-dimethyl-3-thienyl) -N- (2-methoxy-1-methyl-ethyl) -acetamide (dimethenamid), 2-amino-4- (1-fluoro-1-methyl -ethyl) -6- (1-methyl-2- (3,5-dimethyl-phenoxy) -ethylamino) -1,3,5-triazine (dimexyflam), N3, N3-diethyl-2,4-dinitro-6 -trifluoromethyl-1,3-diamino-benzene (dinitramine), 6,7-dihydro-dipyrido [1,2-a: 2 ', 1'-c ] pyrazine diium (diquat), S, S-dimethyl-2-difluoromethyl-4-i-butyl-6-trifluoromethyl pyridine-3,5-dicarbothioate (dithiopyr), N '- (3,4-dichlorophenyl) - N, N -dimethylurea (diuron), 2- [2- (3-chlorophenyl) oxiranylmethyl] -2-ethyl-1H-indene-1,3 (2H) -dione (epropodane), S- Ethyl dipropylthiocarbamate (EPTC), S- (phenylmethyl) -N-ethyl-N- (1,2-dimethyl-propyl) -thiocarbamate (Espro carb), N-ethyl-N- (2-methyl-2-propenyl) -2,6-dinitro-4-trifluoromethyl-benzene amine (ethalfluralin), (S) - (2-ethoxy-1-methyl-2-oxoethyl) -2-chloro-5- (2-chloro-4-trifluoromethyl- phenoxy) benzoate (ethoxyfen), N- (4,6-dimethoxy pyrimidin-2-yl) -N '- (2-ethoxyphenoxysulfonyl) urea (ethoxysulfuron), (R) -ethyl-2- [4- (6-chloro-benzoxazol-2-yl-oxy) phenoxy] propanoate (Fenoxa prop- (P) -ethyl), 4- (2-chloro-phenyl) -N-cyclohexyl-N-ethyl-4,5 -dihydro-5-oxo-1H-tetrazole-1-carboxamide (fentrazamide), isopropyl-N-benzoyl-N- (3-chloro-4-fluro-phenyl) -DL-alaninate (flamprop-isopropyl), isopropyl-N - benzoyl-N- (3-chloro-4-fluro-phenyl) -L-alaninate (Flamprop-isopr opyl-L), methyl-N-benzoyl-N- (3-chloro-4-fluorophenoxy) -DL-alaninate (Flamprop-methyl), N- (2,6-difluorophenyl) -8-fluoro- 5-methoxy- [1,2,4] -triazolo- [1,5-c] pyrimidine-2-sulfonamide (florasulam), (R) -2- [4- (5-trifluoromethyl-pyridin-2-yl -oxy) -phenoxy] -propanoic acid-butyl ester (fluazifop, -butyl, -P-butyl), 5- (4-bromo-1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl) -2-chloro 4-fluoro-benzoic acid i-propyl ester (fluazolates), N- (4-fluoro-phenyl) -ni-propyl-2- (5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy) -acetamide (flufenacet), N- (2,6-difluorophenyl) -5-methyl-1,2,4-triazolo [1,5-a] pyrimidine-2-sulfonamide (flumet sulam), pentyl- [2 -chloro-4-fluoro-5- (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl) phenoxy] acetate (flumiclorac-pentyl), 2- [7-fluoro-3,4-dihydro-3-oxo-4- (2-propynyl) -2H-1,4-benzoxazin-6-yl] -4,5,6,7-tetrahydro-1H- isoindole-1,3-dione (flumioxazin), 2- [4-chloro-2-fluoro-5 - [(1-methyl-2-propynyl) -oxy] - phenyl] -4,5,6,7-tetrahydro -1H-isoindole-1,3 (2H) -dione (flumipropyn), 5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro-benzoic acid-ethoxycarbonylmethyl ester (fluoroglycofen-ethyl), 1- (4-chloro-3- (2,2,3,3,3-pentafluoropropoxy methyl) phenyl) -5-phenyl-1H -1,2,4-triazole-3-carboxamide (flupoxam), 1-isopropyl-2-chloro-5- (3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 ( 2H) - pyrimidyl) benzoate (flupropacil), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (3-methoxycarbonyl-6-trifluoromethyl-pyridin-2-yl-sulfonyl) urea- Sodium salt (flupyrsulfuron-methyl-sodium), 9-hydroxy-9H-fluoren-9-carboxylic acid (flurenol), (4-amino-3,5-dichloro-6-fluoropyridin-2-yl-oxy) acetic acid (-2-butoxy-1-methyl-ethyl ester, -1-methyl-heptyl ester) (fluroxypyr, -butoxypropyl, -meptyl), 5-methylamino-2-phenyl-4- (3-trifluoromethyl-phenyl) -3 ( 2H) -furanone (Flurtamone), methyl - [(2-chloro-4-fluoro-5- (tetrahydro-3-oxo-1H, 3H- [1,3,4] thiadiazolo- [3,4-a] -pyridazin-1-ylidene) -amino-phenyl] -thio acetate (fluthiacetmethyl), 5- (2-chloro-4-trifluoromethyl-phenoxy) -N-methyl sulfonyl-2-nitro-benzamide (Fomesafen), 2-amino -4- (hydroxymethyl phosphinyl) -bu tanoic acid (ammonium salt) (glufosinate (ammonium)), N-phosphonomethyl-glycine (-isopropylammmonium), (glyphosate, -isopropylammonium), N- (4,6-dimethoxy-pyrimidin-2-yl) -N'- (3-chloro-4-methoxy carbonyl-1-methyl-pyrazol-5-yl-sulfonyl) urea (halosulfuron-methyl), (R) -2- [4- (3-chloro-5-trifluoromethyl-pyridine- 2-yl-oxy) -phenoxy] -propanoic acid (-methyl ester, -2-ethoxy-ethyl ester, -butyl ester) (haloxyfop, -methyl, -P-methyl, -ethoxyethyl, -butyl), 3-cyclohexyl-6-dimethylamino -1-methyl-1,3,5-triazine-2,4 (1H, 3H) -dione (hexazinones), methyl-2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo 1H-imidazol-2-yl) -4-methyl-benzoate (Imazametha benz-methyl), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -5-methoxymethyl-pyridine- 3-carboxylic acid (imazamox), 2- (4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl) -quinoline-3-carboxylic acid (imazaduin), 2- (4th , 5-dihydro-4-methyl-4-i-propyl-5-o xo-1H-imidazol-2-yl) -5-ethyl-pyridine-3-carboxylic acid (imazethapyr), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (2-chloro-imidazo [ 1,2- a] pyridin-3-yl-sulfonyl) urea (imazosulfuron), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (5th -iodo-2-methoxycarbonyl-phenylsulfonyl) urea sodium salt (iodosulfuron-methyl-sodium), 4-hydroxy-3,5-diiodobenzonitrile (ioxynil), N, N-dimethyl-N '- (4-isopropyl- phenyl) urea (isoproturon), N- (3- (1-ethyl-1-methylpropyl) isoxazol-5-yl) -2,6-dimethoxybenzamide (isoxa ben), (4-chloro-2 -methylsulfonyl-phenyl) - (5-cyclopropyl-isoxazol-4-yl) - methanone (isoxachlortole), (5-cyclopropyl-isoxazol-4-yl) - (2-methylsulfonyl-4-trifluoromethyl-phenyl) -methanone (isoxaflutole ), 2- [2- [4- [3,5-dichloro-2-pyridinyl) -oxy] -phenoxy] -1-oxo-propyl] -isoxazolidine (isoxapyrifop), (2-ethoxy-1-methyl-2 -oxo-ethyl) -5- (2-chloro-4-trifluoromethyl-phenoxy) -2-nitro benzoate (lactofen), N '- (3,4-dichlorophenyl) -N-methoxy-N-methyl-urea (Linuron), (4-chloro-2-methylphenoxy) acetic acid (MCPA), 2- (4-chloro-2-methylphenoxy) propionic acid (mecoprop), 2- (2-benzothiazolyloxy) -N-methyl-N-phenyl-acetamide (mefenacet), 2- (4-methylsulfonyl-2-nitro benzoyl) -1,3-cyclohexanedione (mesotrione), 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5 (4H) -one (metamitron), 2-chloro-N- (2,6 -dimethyl-phenyl) -N- (1H-pyrazol-1-yl-methyl) -acetamide (metazachlor), N '- (4- (3,4-dihydro-2-methoxy-2,4,4-trimethyl- 2H-1-benzopyran-7-yl-oxy) phenyl) -N-methoxy-N-methylurea (metobenzuron), N '- (4-bromophenyl) -N-methoxy-N-methylurea (metobromuron), ( S) -2-Chloro-N- (2-ethyl-6-methyl-phenyl) - N- (2-methoxy-1-methyl-ethyl) -acetamide (metolachlor, S-metolachlor), N- (2nd , 6-dichloro-3-methylphenyl) -5,7-dimethoxy-1,2,4-triazolo [1,5-a] pyrimi din-2-sulfonamide (metosulam), N '- (3-chloro -4-methoxy-phenyl) -N, N-dimethyl-urea (metoxuron), 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5 (4H) -one (metribuzin ), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonylphenylsulfonyl) urea (metsulfuron-methyl), S-ethyl hexahydro-1H-azepine-1-carbothioate (Molinate), 2- (2-naphthyloxy) -N-phenyl-propanamide (Naproanilide), N-butyl-N '- (3,4-dichlorophenyl) -N-methyl -urea (neburon), N- (4,6-dimethoxypyrimidin-2-yl) -N '- (3-di methylcarbamoyl-pyridin-2-yl-sulfonyl) urea (nicosulfuron), S- (2- Chlorobenzyl) -N, N-diethyl-thiocarbamate (Orbencarb), 4-dipropylamino-3,5-dinitro-benzenesulfonamide (Oryzalin), 3- [2,4-dichloro-5- (2-propynyloxy) phenyl] -5- (t-butyl) -1,3,4-oxadiazol-2 (3H) -one (oxadiargyl), 3- [2,4-dichloro-5- (1-methylethoxy) phenyl] -5 - (t-Butyl) -1,3,4-oxadiazol-2 (3H) -one (oxadiazon), N- (4,6-dimethyl-pyrimidin-2-yl) -N '- (2-oxetan-3 -yl-oxycarbonyl-phenylsulfonyl) urea (oxasulfuron), 3- [1- (3,5-dichlorophenyl) -1-i-propyl] -2,3-di hydro-6-methyl-5-phenyl -4H-1,3-oxazin-4-one (oxaziclomefone), 2-chloro-1- (3-ethoxy-4-nitro-phenoxy) -4-trifluoromethyl-benzene (oxyfluorfen), 1,1'-dimethyl -4,4'-bipyridinium (paraquat), 1-amino-N- (1-ethyl-propyl) -3,4-di methyl-2,6-dinitro-benzene (pendimethalin), 4- (t-butyl) -N- (1st -ethyl-propyl) - 2,6-dinitro-benzenamine (pendralin), 4-amino-3,5,6-trichloropyridine-2-carboxylic acid (picloram), 2-chloro-N- (2,6- diethyl-phenyl) -N- (2-propoxy-ethyl) -acetamide (pretilachlor), N- (4-fluorophenyl) -6- (3-trifluoromethyl-phenoxy) -pyridine-2-carboxamide (picolinafen), N- (4,6-bis-difluoromethoxypyrimidin-2-yl) -N '- (2-methoxycarbonyl-phenylsulfonyl) urea (primisulfuron methyl), 2-chloro-N-isopropyl-N-phenyl-acetamide (propachlor ), N- (3,4-Di chlorophenyl) propanamide (propanil), 2-chloro-N- (2-ethyl-6-methylphenyl) - N - [(1-methylethoxy) methyl ] -acetamide (propisochlor), S-phenylmethyl-N, N-dipropyl-thiocarbamate (prosulfocarb), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- ( 2- (3,3,3-trifluoropropyl) phenylsulfonyl) urea (Pro sulfuron), ethyl- [2-chloro-5- (4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl ) -4-fluorophenoxy] acetate (pyraflufen-ethyl), 4- (2,4-dichlorobenzoyl) -1,3-dimethyl-5- (4-methylphenylsulfonyloxy) pyrazole (pyrazolates), 4 - (2,4-Di chloro-benzoyl) -1,3-dimethyl-5- (phen ylcarbonylmethoxy) pyrazole (pyrazoxy fen), N- (4,6-dimethoxy-pyrimidin-2-yl) -N '- (4-ethoxycarbonyl-1-methyl pyrazol-5-yl-sulfonyl) urea (pyrazosulfuron-ethyl ), Diphenylmethanone- O- [2,6-bis- (4,6-dimethoxypyrimidin-2-yloxy) benzoyl] oxime (pyribenz oxime), 6-chloro-3-phenyl-4-pyridazinol ( Pyridafol), O- (6-chloro-3-phenylpyridazin-4-yl) -S-octylthiocarbonate (pyridate), 6-chloro-3-phenylpyridazin-4-ol (pyridatol), 2- (4.6 -Dimethoxy-pyrimidin-2-yl-oxy) -benzoic acid methyl ester (Pyriminobac-methyl), 2-chloro-6- (4,6-dimethoxy-pyrimidin-2-ylthio) - benzoic acid sodium salt (Pyrithiobac-sodium) , 7-chloro-3-methyl-quinoline-8-carboxylic acid (Quinmerac), 2- [4- (6-chloro-2-quinoxalinyloxy) phenoxy] propanoic acid (ethyl ester, tetrahydro-2-furanyl methyl ester) (Quizalofop, -ethyl, -P-ethyl, -P-tefuryl), N- (4,6-Dimethoxy-pyrimidin-2-yl) -N '- (3-ethyl sulfonyl-pyridin-2-yl-sulfonyl) urea (rimsulfuron), 2- (1-ethoximino butyl) -5- (2-ethylthiopropyl) -3-hydroxy-2-cyclohexen-1-one (sethoxydim), 6-chloro-2,4- bis-ethylamino-1,3,5-triazine (simazine), 2- (2-chloro-4-methyl sulfonyl-benzoyl) cyclohexane-1,3-dione (sulcotrione), 2- (2,4-dichloro- 5-methylsulfonylamino-phenyl) -4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (sulfentrazone), N-phosphonomethyl-glycine trimethyl sulfonium (sulfosate), N- (4,6-Dimethoxypyrimidin-2-yl) -N '- (2-ethylsulfonylimidazo [1,2-a] pyridine-3-sulfonamide (sulfosulfuron), 6-chloro-4-ethylamino- 2-tert-butylamino-1,3,5-triazine (terbuthylazine), 2-tert-butyl amino-4-ethylamino-6-methylthio-1,3,5-triazine (terbutryn), 2-chloro-N- ( 2,6-dimethyl-phenyl) -N- (3-methoxy-2-thienyl-methyl) -acetamide (thenylchlor), 2-difluoromethyl-5- (4,5-dihydro-thiazol-2-yl) -4- (2-methyl-propyl) -6-trifluoromethyl-pyridine-3-carboxylic acid methyl ester (thiazopyr), 6- (6,7-dihydro-6,6-dimethyl-3H, 5H-pyrrolo [2,1-c ] -1,2,4-thiadiazol-3-ylidenamino) -7-fluoro-4- (2-propynyl) -2H-1,4-benzoxazin-3 (4H) -one (thidiazimin), N- (4- Methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxycarbonylthien-3-yl-sulfonyl) -h arn substance (thifensulfuron-methyl), 2- (ethoximino-propyl) -3-hydroxy-5- (2,4,6-tri methyl-phenyl) -2-cyclohexen-1-one (tralkoxydim), S- (2nd , 3,3-trichloro-2-propenyl) diisopropyl carbamothioate (triallate), N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- [2- (2- chloroethoxy) phenylsulfonyl] urea (triasulfuron), N-methyl-N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -N '- (2-methoxy carbonyl -phenylsulfonyl) urea (tribenuron-methyl), (3,5,6-trichloro) - pyridin-2-yl-oxy-acetic acid (triclopyr), 2- (3,5-dichloro-phenyl) -2- (2nd , 2,2-tri chloroethyl) oxirane (tridiphane), 1-amino-2,6-dinitro-N, N-dipropyl-4-tri fluoromethyl-benzene (trifluralin), N- [4-dimethylamino-6 - (2,2,2-trifluoroethoxy) -1,3,5-triazin-2-yl] -N '- (2-methoxycarbonylphenylsulfonyl) urea (triflusulfuron-methyl), N- (4-methoxy- 6-trifluoromethoxy-1,3,5-triazin-2-yl) - N '- (2-trifluoromethyl-phenylsulfonyl) urea (tritosulfuron), 2-pyridinesulfonamide, N - [[(4,6-dimethoxy-2 -pyrimidinyl) amino] carbonyl] -3- [methyl (methylsulfonyl) amino] (WO-A-92/10660 ), Benzoic acid, 2 - [[[((4,6-dimethoxy-2-pyrimidinyl) amino] carbonyl] amino] sulfonyl] -4 - [[(methylsulfonyl) amino] methyl], methyl ester (DE-A 43 35 297)
  ("Active substances of group 2")
  and if necessary
• 3. at least one compound improving the tolerance of crop plants from the following group of compounds:
  α- (1,3-dioxolan-2-yl-methoximino) -phenylacetonitrile (oxabetrinil), α- (cya nomethoximino) -phenylacetonitrile (cyometrinil), 4-chloro-N- (1,3-dioxolan-2-yl- methoxy) -α-trifluoro-acetophenone oxime (fluxofenim), 4,6-dichloro-2-phenyl pyrimidine (fenclorim), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor ), 5-chloro-quinoxaline-8-oxyacetic acid (1-methyl-hexyl ester) (Cloquintocet), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) -ethyl) - N- (2-propenyl) acetamide (DKA-24), 1,8-naphthalic anhydride, 1- (2,4-di chlorophenyl) -5-trichloromethyl-1H-1,2,4-triazole-3- ethyl carboxylate (fenchlorazole-ethyl), 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid phenyl methyl ester (flurazole), 3-dichloroacetyl-5- (2-furanyl) -2,2-dimethyl-oxazolini din ( Furilazole, MON-13900), 4-dichloroacetyl-1-oxa-4-azaspiro [4.5] decan (AD-67), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2, 2-dichloro-N- (1,3-dioxolan-2-yl-methyl) -N- (2-propenyl) acetamide (PPG-1292), 2,2-di chloro-N, N-di-2- propenyl acetamide (dichlorom d), N- (4-methyl-phenyl) -N '- (1-methyl-1-phenyl-ethyl) -urea (Dymron), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo [1,2 -a] -pyrimidine-6 (2H) -one (BAS-145138), N- (2-methoxy-benzoyl) -4- (methylaminocarbonylamino) -benzenesulfonamide, ethyl-4,5-dihydro-5,5-diphenyl- 3-isoxazole carboxylate (isoxadifen-ethyl), diethyl-1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (Me fenpyr-diethyl) and 2.4 -Dichlorophenoxyacetic acid (2,4-D) and its derivatives
  ("Active substances of group 3").

2. Composition according to claim 1, characterized in that
R ¹ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine and / or chlorine,
R ² represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine and / or chlorine,
R ^{3 represents} hydrogen, fluorine, chlorine or bromine,
R ^{4 represents} cyano, thiocarbamoyl, fluorine, chlorine or bromine,
R ⁵ for nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, hydroxyamino, aminosulfonyl, fluorine, chlorine, bromine, for each optionally by cyano, hydroxy, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl and / or ethoxy carbonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, Methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i-propyl amino, n-, i-, s- or t-butylamino, for ethenyl optionally substituted by cyano, carboxy, fluorine, chlorine, bromine, methoxycarbonyl and / or ethoxycarbonyl , Propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy, each optionally with fluorine and / or chlorine substituted acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino, n-, i-, s- or t-butylsulfonylamino, N, N-bis-methylsulfonylamino, N, N-N -amino, N-ethyl sulfonyl-N-methylsulfonyl-amino, N-acetyl-N-methylsulfonyl-amino, N-propionyl-N-methylsulfonyl-amino, Nn-butyroyl-N-methyl sulfonyl-amino, Ni-butyroyl-N -methylsulfonyl-amino, Ns-butyroyl-N-methylsulfonyl-amino, N-pivaloyl-N-methylsulfonyl-amino, N-acetyl-N-ethylsulfonyl-amino, N-propionyl-N-ethylsulfonyl-amino, Nn-butyroyl-N -ethylsulfonyl-amino, Ni-butyroyl-N-ethylsulfonyl-amino, Ns-butyroyl-N-ethylsulfonyl-amino, N-pivaloyl-N-ethyl sulfonyl-amino, or for each optionally by cyano, fluorine, chlorine, bromine, methyl, Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluonomethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted N-phenylcarbonyl-N-methyl sulfonylamino, N-phenylcar bonyl-N-ethylsulfonyl-amino, N-thienylcarbonyl-N-methylsulfonyl-amino or N-thienylcarbonyl-N-ethylsulfonyl-amino. 3. Means according to claim 1, characterized in that
R ¹ represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine and / or chlorine,
R ² represents methyl, ethyl, n- or i-propyl, each optionally substituted by fluorine and / or chlorine,
R ^{3 represents} hydrogen, fluorine or chlorine,
R ^{4 represents} cyano or thiocarbamoyl, and
R ⁵ for nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, mercapto, amino, hydroxyamino, aminosulfonyl, fluorine, chlorine, bromine, for each optionally by cyano, hydroxy, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl and / or ethoxy carbonyl substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxy carbonyl, n- or i-propoxycarbonyl, methylamino, ethylamino, n- or i-propylamino, for ethenyl optionally substituted by cyano, carboxy, fluorine, chlorine, bromine, methoxycarbonyl and / or ethoxycarbonyl , Propenyl, ethynyl, propynyl, propenyloxy or propynyloxy for acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonyl, each optionally substituted by fluorine and / or chlorine amino, N, N-bis-methylsulfonyl-amino, N, N-bis-ethylsulfonyl-amino, N-ethylsulfonyl-N-methylsulfonyl-amino, N-acetyl-N-methylsulfonyl-amino, N-propionyl-N-methylsulfonyl- amino, Nn-butyroyl-N-methylsulfonyl-amino, Ni-butyroyl-N-methylsulfonyl-amino, Ns-butyroyl-N-methylsulfonyl-amino, N-pivaloyl-N-methylsulfonyl-amino, N-acetyl-N-ethylsulfonyl- amino, N-propionyl-N-ethylsulfonyl-amino, Nn-butyroyl-N-ethylsulfonyl amino, Ni-butyroyl-N-ethylsulfonyl-amino, Ns-butyroyl-N-ethyl sulfonyl-amino, N-pivaloyl-N-ethylsulfonyl- amino, or for each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy-substituted N-phenylcarbonyl-N-methylsulfonyl-amino, N-phenyl carbonyl-N-ethylsulfonyl-amino , N-thienylcarbonyl-N-methyl sulfonyl-amino or N-thienylcarbonyl-N-ethylsulfonyl-amino. 4. Agent according to one of claims 1 to 3, characterized in that the active ingredient of group 1 is selected from the following compounds:
2- (4-cyano-2-fluoro-5-methylsulfonylamino-phenyl) -4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- ( 4-cyano-2-fluoro-5-ethylsulfonylamino-phenyl) -4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-cyano -2-fluoro-5-methylsulfonylamino-phenyl) -4-methyl-5-difluoro methyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-cyano-2- fluoro-5-ethyl sulfonylaminophenyl) -4-methyl-5-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-cyano-2-fluoro-5 -methylsulfonylamino-phenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-cyano-2-fluoro-5-ethyl sulfonylamino- phenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-cyano-2-fluoro-5-methylsulfonylamino-phenyl) -4 -ethyl-5-difluoro methyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-cyano-2-fluoro-5-ethyl sulfonylaminophenyl) -4-ethyl -5-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-thiocarbamoyl-2-fluoro-5-methylsulfonylamino-phenyl) -4-methyl-5-trifluoromethyl -2,4-dihydro-3H-1,2,4-triazol-3-one, 2 - (4-Thiocarbamoyl-2-fluoro-5-ethylsulfonylamino-phenyl) -4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4- Thiocarbamoyl-2-fluoro-5-methylsulfonylamino phenyl) -4-methyl-5-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-thiocarbamoyl-2-fluoro -5-ethylsulfonylamino-phenyl) -4-methyl-5-difluoro methyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-thiocarbamoyl-2-fluoro-5- methylsulfonylamino-phenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-thiocarbamoyl-2-fluoro-5-ethylsulfonylamino-phenyl) -4- ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-thio carbamoyl-2-fluoro-5-methylsulfonylamino-phenyl) -4- ethyl-5-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2- (4-thiocarbamoyl-2-fluoro-5-ethyl sulfonylamino-phenyl) -4-ethyl-5 -difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one. 5. Means according to claim 4, characterized in that the active ingredient Group 1 the compound 2- (4-thiocarbamoyl-2-fluoro-5-ethylsulfonylamino phenyl) -4-methyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one. 6. Composition according to one of claims 1 to 5, characterized in that the Active ingredient of group 2 is selected from atrazine, bromoxynil, chlorine imuron-ethyl, clodinafop-propargyl, dicamba, dichlorprop-P, diflufenican, Dimethenamid, fenoxaprop- (P) -ethyl, fentrazamide, flufenacet, flupyrsulf  uron-methyl-sodium, flurtamone, glufosinate-ammonium, glyphosate-iso propylammonium, imazamethapyr, imazamox, iodosulfuron-methyl-sodium, Mesotrione, Metolachlor, Metosulam, Metribuzin, Metsulfuron-methyl, Nico sulfuron, rimsulfuron, sulcotrione, sulfosate, sulfosulfüron, terbuthylazine, Thifensulfuron-methyl, tralkoxydim, tribenuron-methyl. 7. Composition according to one of claims 1 to 6, characterized in that the Active ingredient of group 3 is selected from 5-chloro-quinoxaline-8-oxy-vinegar acid (1-methylhexyl ester) (cloquintocet), 1- (2,4-dichlorophenyl) -5-trichlor methyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazole-ethyl), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazole carboxylate (isoxadifen-ethyl), diethyl-1 (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (Mefenpyr-diethyl) and 2,4-dichlorophenoxyacetic acid (2,4-D) and its Derivatives. 8. Composition according to one of claims 1 to 7, characterized in that on 1 part by weight of active ingredient from the group 0.01 to 1000 parts by weight, preferably as 0.02 to 500 parts by weight, particularly preferably 0.05 to 100 Ge important parts of Group 2 active ingredient are eliminated. 9. Use of an agent according to one of claims 1 to 7 for loading fight from unwanted plants.