Claims
- 1. Selective-herbicidal compositions, characterized by a content of an active compound combination consisting of
- (a) a heteroaryloxy-acetamide of the general formula (I) ##STR3## in which Het represents thiadiazolyl which is substituted by halogen or by C.sub.1-C.sub.4 -alkyl or phenyl, each of which is optionally substituted by halogen, and
- Ar represents phenyl which is optionally substituted by halogen, C.sub.1-C.sub.4 -alkyl or C.sub.1-C.sub.4 -halogenoalkyl, ("active compounds of group 1") and
- (b) one or more compounds from a second group of herbicides which contains the active compounds mentioned below: N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-chloro-4-methoxycarbonyl-1-methyl -pyrazol-5-yl-sulfonyl)-urea(clopyrasulfuron, halosulfuron,NC-319),2-chloro-N -(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methyl-ethyl)-acetamide (dimethenamid, SAN-582),2-chloro-N-(2,6-dimethyl-phenyl)-N-(1H-pyrazol-1-yl-methyl)-acetamide (metazachlor), N-4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-ethylsulfonyl-pyridin-2-yl-sulfonyl)-urea (rimsulfuron), 3-i-propyl-1H-2,1,3-benzothiadiazin-4(3H)-one (bentazone), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), 3,6-dichloro-2-methoxybenzoic acid (dicamba), 2,4-dichloro -phenoxyacetic acid (2,4-D), O-(6-chloro-3-phenyl-pyridazin-4-yl) S-octyl thiocarbonate(pyridate),(4-amino-3,5-dichloro-6-fluoro-pyridin-2-yl-oxy)-acetic acid (fluroxypyr), N-(2,6-difluoro-phenyl)-5-methyl-1,2,4-triazolo�1,5-a!-pyrimidine-2-sulphonamide (flumetsulam, DE-498), N-(2,6-dichloro-3-methyl -phenyl)-5,7-dimethoxy-1,2,4-triazolo�1,5-a!-pyrimidine-2-sulphonamide (metosulam, DE-511),N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N-(2-(3,3,3-trifluoropropyl)-phenylsulphonyl)-urea(prosulfuron),5-(N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthio-phenyl)-imino)-tetrahydro-3-oxo-1H,3H-1,3,4-thiadiazolo�3,4-a!-pyridazine (KIH-9201), 2-(2-chloro-4-methylsulphonyl benzoyl) cyclohexane-1,3-dione (sulcotrione), N'-(4-(3,4-dihydro-2-methoxy -2,4,4-trimethyl-2H-1-benzopyran-7-yl-oxy)-phenyl)-N-methoxy-N-methyl-urea (metobenzuron, UMP-488),3-amino-2,5-dichloro-benzoic acid (chloramben),2-(2-chloro-phenyl-methyl)-4,4-dimethyl-isoxazolidin-3-one (clomazone), 2-(2,4-dichloro-5-methylsulphonylamino-phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (sulfentrazone, F-6285),2-(4,5-dihydro-4-methyl -4-i-propyl-5-oxo-1H-imidazol-2-yl)-5-ethyl-pyridine-3-carboxylic acid (imazethapyr), 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo-1H-imidazol-2-yl)-5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoic acid ethoxycarbonylmethyl ester (fluoroglycofen-ethyl), 4-dipropylamino-3,5-dinitro-benzenesulphonamide (oryzalin),S-phenylmethylN,N-dipropyl-thiocarbamate(prosulfocarb),3-chloro -4-chloromethyl-1-(3-trifluoromethyl-phenyl)-pyrrolidin-2-one (fluorochloridone), 2-chloro-6-nitro-3-phenoxy-benzenamine (aclonifen), N'-(4-bromo-phenyl)-N -methoxy-N-methylurea (metobromuron), 9-hydroxy-9H-fluoren-9-carboxylic acid (flurenol),7-chloro-3-methyl-quinoline-8-carboxylic acid (quinmerac), 4-hydroxy-3,5-diiodo-benzonitrile (ioxynil), N-(3-(1-ethyl-1-methyl-propyl) -isoxazol-5-yl)-2,6-dimethoxy-benzamide (isoxaben), N'-(3-chloro-4-methoxy -phenyl)-N,N-dimethyl-urea (metoxuron), N-butyl-N'-(3,4-dichloro-phenyl)-N-methyl-urea (neburon),(4-chloro-2-methyl-phenoxy)-acetic acid (MCPA), 2-(4-chloro-2-methyl-phenoxy)-propionic acid (mecoprop),3,5-dibromo-4-hydroxy benzaldehyde O-(2,4-dinitro-phenyl) oxime (bromofenoxim), 4-chloro-2-oxo-3(2H)-benzothiazoleacetic acid (benazolin), 3,6-dichloro-pyridine-2-carboxylic acid (clopyralid), 2-(4-chloro-2-fluoro-5-(2-chloro-2-ethoxycarbonyl-ethyl) -phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one(F-8426),1-(4-chloro-3-(2,2,3,3,3-pentafluoro-propoxymethyl)-phenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide (flupoxam), 6-(6,7-dihydro-6,6-dimethyl-3H,5H-pyrrolo �2,1-c!-1,2,4-thiadiazol-3-ylideneamino)-7-fluoro-4-(2-propinyl)-2H-1,4benzoxazin-3-(4H)-one (thidiazimin), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(2-cyclopropylcarbonyl-phenyl-sulphonyl)-urea (AC-322140), 4-chloro-3-(4-chloro -2-fluoro-5-ethoxycarbonyl-methoxy)-5-difluoromethoxy-1-methyl-pyrazole (ET-751), N-butoxymethyl-2-chloro-N-(2,6-diethyl-phenyl)-acetamide(butachlor),2-chloro-N-(2,6-diethyl-phenyl)-N-(2-propoxy-ethyl)-acetamide (pretilachlor), S-(phenylmethyl) N-ethyl-N-(1,2-dimethyl-propyl)-thiocarbamate (esprocarb), N-(4-methyl-phenyl)-N'-(1-methyl-1-phenyl-ethyl)-urea (dymron), 4-(2,4-dichloro-benzoyl)-1,3-dimethyl-5-(4-methyl-phenyl-sulphonyloxy)-pyrazole (pyrazolate), 4-(2,4-dichloro-benzoyl)-1,3-dimethyl-5-phenyl-carbonylmethoxy) -pyrazole(pyrazoxyfen), N-(4,6-dimethoxy-1,3,5-triazin-2-yl-N'-(2-(2-methoxy -ethoxy)-phenylsulphonyl)-urea (cinosulfuron), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'- (4-ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulphonyl)-urea (pyrazosulfuron -ethyl),N-4,6-dimethoxy-pyrimidin-2-yl)-N'-(2-chloro-imidazo�1,2-a!-pyridin-3-yl-sulphonyl-urea (imazosulfuron), S,S-dimethyl 2-difluoromethyl-4-i-butyl-6-trifluoromethyl-pyridine-3,5-dicarbothioate(dithiopyr),2-bromo-3,3-dimethyl-N -(1-methyl-1-phenyl-ethyl)-butanamide (bromobutide), 2-(2-naphthyloxy)-N -phenyl-propanamide (naproanilide), 2-chloro-N-(2,6-dimethyl-phenyl)-N-(3-methoxy-2-thienyl-methyl)-acetamide (thenylchlor), 1,3,5-trichloro-2-(4-nitro -phenoxy)-benzene (chlornitrofen),2,4-dichloro-1-(3-methoxy-4-nitro-phenoxy)-benzene (chlomethoxyfen) - ("active compounds of group 2") - and/or
- (c) a compound which improves the tolerance by crop plants, from the following group of compounds: a-(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil), a-(cyanomethoximino)-phenylacetonitrile(cyometrinil),4-chloro-N-(1,3-dioxolan -2-yl-methoxy)-a-trifluoro-acetophenone oxime (fluxofenim), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), 4dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine(benoxacor),5-chloro-quinoxalin-8-oxy-acetic 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-dichloro -phenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazol-ethyl), 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid phenylmethyl ester (flurazole), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl -oxazolidine (furilazole, MON-13900), 4-dichloroacetyl-1-oxa-4-azaspiro�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-dichloro-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-trimethylpyrrolo�1,2-a!-pyrimidin-6(2H)-one (BAS-14538), N-(2-methoxy -benzoyl)4-(methylaminocarbonylamino)-benzenesulphonamide-("antidotes" or ("safeners") from 0.001 to 1000 parts by weight of an active compound of group 2 and/or from 0.001 to 1000 parts by weight of one of the abovementioned antidotes/safeners being present per part by weight of an active compound of group 1 (i.e. of the formula (I)).
- 2. Selective-herbicidal compositions, characterized by a content of an active compound combination consisting of
- (a) a heteroaryloxy-acetamide of the general formula (I) according to claim 1, in which
- Het represents 1,2,4-thiadiazolyl or 1,3,4-thiadiazolyl, which is substituted by fluorine, chlorine, bromine or by methyl, ethyl, n- or i-propyl or phenyl, each of which is optionally substituted by fluorine and/or chlorine, and
- Ar represents phenyl which is optionally substituted by fluorine, chlorine, bromine, methyl or trifluoromethyl,
- ("active compounds of group 1") and
- (b) one or two compounds from a second group of herbicides which contains the active compounds mentioned below: N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-chloro-4-methoxycarbonyl-1-methyl pyrazol-5-yl-sulfonyl)-urea(clopyrasulfuron,halosulfuron,NC-319),2-chloro-N (2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methyl-ethyl)-acetamide (dimethenamid, SAN-582),2-chloro-N-(2,6-dimethyl-phenyl)-N-(1H-pyrazol-1-yl-methyl)-acetamide (metazachlor), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-ethylsulfonyl-pyridin-2-yl-sulfonyl)-urea (rimsulfuron), 3-i-propyl-1H-2,1,3-benzothiadiazin-4(3H)-one (bentazone), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), 3,6-dichloro-2-methoxybenzoic acid (dicamba), 2,4-dichloro -phenoxyacetic acid (2,4-D), O-(6-chloro-3-phenyl-pyridazin-4-yl) S-octyl thiocarbonate(pyridate),(4-amino-3,5-dichloro-6-fluoro-pyridin-2-yl-oxy)-acetic acid (fluroxypyr), N-(2,6-difluoro-phenyl)-5-methyl-1,2,4-triazolo�1,5-a!-pyrimidine-2-sulphonamide (flumetsulam, DE498), N-(2,6-dichloro-3-methyl -phenyl)-5,7-dimethoxy-1,2,4-triazolo�1,5-a!-pyrimidine-2-sulphonamide (metosulam, DE-511), N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-(3,3,3-trifluoropropyl)-phenylsulphonyl)-urea(prosulfuron),5-(N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthio-phenyl)-imino)-tetrahydro-3-oxo-1H,3H-1,3,4-thiadiazolo�3,4-a!-pyridazine (KIH-9201), 2-(2-chloro-4-methylsulphonyl-benzoyl) cyclohexane-1,3-dione (sulcotrione), N'-(4-(3,4-dihydro-2-methoxy 2,4,4-trimethyl-2H-1-benzopyran-7-yl-oxy)-phenyl)-N-methoxy-N-methyl-urea (metobenzuron, UMP-488),3-amino-2,5-dichloro-benzoic acid (chloramben),2-(2-chloro-phenyl-methyl)-4,4-dimethyl-isoxazolidin-3-one (clomazone), 2-(2,4-dichloro-5-methylsulphonylamino-phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (sulfentrazone, F-6285),2-(4,5-dihydro-4-methyl -4-i-propyl-5-oxo-1H-imidazol-2-yl)-5-ethyl-pyridine-3-carboxylic acid (imazethapyr), 2-(4,5-dihydro-4-i-propyl-5-oxo-1H-imidazol-2-yl)-5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoic acid ethoxycarbonylmethyl ester (fluoroglycofen-ethyl), 4-dipropylamino-3,5-dinitro-benzenesulphonamide (oryzalin),S-phenylmethylN,N-dipropyl-thiocarbamate (prosulfocarb),3-chloro -4-chloromethyl-1-(3-trifluoromethyl-phenyl)-pyrrolidin-2-one (fluorochloridone), -2-chloro -6-nitro-3-phenoxy-benzenamine (aclonifen), N'-(4-bromo-phenyl)-N -methoxy-N-methylurea (metobromuron), 9-hydroxy-9H-fluoren-9-carboxylic acid (flurenol), 7-chloro-3-methyl-quinoline-8-carboxylic acid (quinmerac), 4-hydroxy-3,5-diiodo-benzonitrile (ioxynil), N-(3-(1-ethyl-1-methyl-propyl) isoxazol-5-yl)-2,6-dimethoxy-benzamide (isoxaben), N'-(3-chloro-4methoxy -phenyl)-N,N-dimethyl-urea (metoxuron), N-butyl-N'-(3,4-dichloro-phenyl)-N -methyl-urea(neburon), (4-chloro-2-methyl-phenoxy)-acetic acid (MCPA),2-(4-chloro-2-methyl-phenoxy)-propionic acid (mecoprop),3,5-dibromo-4-hydroxy-benzaldehyde O-(2,4-dinitro-phenyl) oxime (bromofenoxim), 4-chloro-2-oxo 3(2H)-benzothiazoleacetic acid (benazolin), 3,6-dichloro-pyridine-2-carboxylic acid (clopyralid), 2-(4-chloro-2-fluoro-5-(2-chloro-2-ethoxycarbonyl-ethyl) -phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one(F-8426), 1-(4-chloro-3-(2,2,3,3,3-pentafluoro-propoxymethyl)-phenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide (flupoxam), 6-(6,-dihydro-6,6-dimethyl-3H,5H pyrrolo�2,1-c!-1,2,4-thiadiazol-3-ylideneamino)-7-fluoro-4(2-propinyl)-2H-1,4-benzoxazin-3(4H)-one (thidiazimin), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(2cyclopropylcarbonyl-phenyl-sulphonyl)-urea (AC-322140),4-chloro-3-(4-chloro 2-fluoro-5-ethoxycarbonyl-methoxy)-5-difluoromethoxy-1-methyl-pyrazole(ET-751), N-butoxymethyl-2-chloro-N-(2,6-diethyl-phenyl)-acetamide(butachlor),2chloro-N-(2,6-diethyl-phenyl)-N-(2-propoxy-ethyl)-acetamide (pretilachlor), S-(phenylmethyl) N-ethyl-N-(1,2-dimethyl-propyl)-thiocarbamate (esprocarb), N-(4-methyl-phenyl)-N'-(1-methyl-1-phenyl-ethyl)-urea (dymron), 4-(2,4-dichloro-benzoyl)-1,3-dimethyl-5-(4-methyl-phenyl-sulphonyloxy)-pyrazole (pyrazolate),4-(2,4-dichloro-benzoyl)-1,3-dimethyl-5-(phenyl-carbonylmethoxy) -pyrazole (pyrazoxyfen), N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N'-(2-(2-methoxy -ethoxy)-phenylsulphonyl)-urea (cinosulfuron), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(4-ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulphonyl)-urea (pyrazosulfuron-ethyl), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(2-chloro-imidazo�1,2-a!-pyridin-3-yl-sulphonyl)-urea (imazosulfuron),S,S-dimethyl2-difluoromethyl-4-i-butyl-6-trifluoromethyl-pyridine-3,5-dicarbothioate (dithiopyr),2-bromo-3,3-dimethyl-N -(1-methyl-1-phenyl-ethyl)-butanamide (bromobutide), 2-(2-naphthyloxy)-N- -phenyl-propanamide (naproanilide), 2-chloro-N-(2,6-dimethyl-phenyl)-N-(3-methoxy-2-thienyl-methyl)-acetamide (thenylchlor), 1,3,5-trichloro-2-(4-nitro-phenoxy)-benzene (chlornitrofen),2,4-dichloro-1-(3-methoxy-4-nitro-phenoxy)-benzene (chlomethoxyfen) - ("active compounds of group 2") - and/or
- (c) a compound which improves the tolerance by crop plants, from the following group of compounds: a-(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil), a-(cyanomethoximino)-phenylacetonitrile (cyometrinil),4-chloro-N-(1,3-dioxolan -2-yl-methoxy)-a-trifluoro-acetophenone oxime (fluxofenim), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor),5-chloro-quinoxalin-8-oxy-acetic acid 1-methyl-hexyl ester (cloquintocet), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2propenyl)-acetamide (DKA-24), 1,8-naphthalic anhydride, 1-(2,4-dichloro phenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazol-ethyl), 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid phenylmethyl ester (flurazole), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl -oxazolidine (furilazole, MON-13900), 4-dichloroacetyl-1-oxa-azaspiro�4.5!(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-dichloro-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-trimethylpyrrolo�1,2-a!-pyrimidin-6(2H)-one (BAS-145138), N-(2-methoxy -benzoyl)-4-(methylaminocarbonylamino)-benzenesulphonamide - ("antidotes" or "safeners") -from 0.01 to 100 parts by weight of an active compound of group 2 and/or from 0.01 to 100 parts by weight of one of the abovementioned antidotes/safeners being present per part by weight of an active compound of group 1 (i.e. of the formula (I)).
- 3. Selective-herbicidal compositions, characterized by a content of an active compound combination consisting of
- (a) a heteroaryloxy-acetamide of the general formula (I) according to claim 1, in which
- Het represents 1,2,4-thiadiazolyl or 1,3,4-thiadiazolyl, which is substituted by chlorine, dichloromethyl, difluoromethyl, trichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl or pentafluoroethyl, and
- Ar represents phenyl which is optionally substituted by fluorine, chlorine, methyl or trifluoromethyl,
- ("active compounds of group 1") and
- (b) one or two compounds from a second group of herbicides which contains the active compounds mentioned below: N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-chloro-4-methoxycarbonyl-1-methyl -pyrazol-5-yl-sulfonyl)-urea(clopyrasulfuron, halosulfuron,NC-319),2-chloro-N (2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methyl-ethyl)-acetamide (dimethenamid,SAN-582),2-chloro-N-(2,6-dimethyl-phenyl)-N-(1H-pyrazol-1-yl-methyl-acetamide (metazachlor), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-ethylsulfonyl-pyridin-2-yl-sulfonyl)-urea (rimsulfuron), 3-i-propyl-1H-2,1,3-benzothiadiazin-4(3H)-one (bentazone), 3,5-dibromo-4-hydroxy-benzonitrile (bromoxynil), 3,6-dichloro-2-methoxybenzoic acid (dicamba), 2,4-dichloro phenoxyacetic acid (2,4-D), O-(6-chloro-3-phenyl-pyridazin-4-yl) S-octyl thiocarbonate(pyridate),(4-amino-3,5-dichloro-6-fluoro-pyridin-2-yl-oxy)-acetic acid (fluroxypyr), N-(2,6-difluoro-phenyl)-5-methyl-1,2,4-triazolo�1,5-a!-pyrimidine-2-sulphonamide (flumetsulam, DE-498), N-(2,6-dichloro-3-methyl -phenyl)-5,7-dimethoxy-1,2,4-triazolo�1,5-a!-pyrimidine-2-sulphonamide (metosulam, DE-511), N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-(3,3,3-trifluoropropyl)-phenylsulphonyl)-urea (prosulfuron),5-(N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthio-phenyl)-imino)-tetrahydro-3-oxo-1H,3H- 1,3,4-thiadiazolo�3,4-a!-pyridazine (KIH-9201), 2-(2-chloro-4-methylsulphonyl -benzoyl)cyclohexane-1,3-dione (sulcotrione), N'-(4-(3,4-dihydro-2-methoxy -2,4,4-trimethyl-2H-1-benzopyran-7-yl-oxy)-phenyl)-N-methoxy-N-methyl-urea (metobenzuron,UMP-488),3-amino-2,5-dichloro-benzoic acid(chloramben), 2-(2-chloro-phenyl-methyl)-4,4-dimethyl-isoxazolidin-3-one (clomazone), 2-(2,4-dichloro-5-methylsulphonylamino-phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (sulfentrazone, F-6285), 2-(4,5-dihydro-4-methyl 4-i-propyl-5-oxo-1H-imidazol-2-yl)-5-ethyl-pyridine-3-carboxylic acid (imazethapyr), 2-(4,5-dihydro-4-methyl-4-propyl-5-oxo-1H-imidazol-2-yl)-5-methyl-pyridine-3-carboxylic acid (imazamethapyr), 5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoic acid ethoxycarbonylmethyl ester (fluoroglycofen-ethyl), 4-dipropylamino-3,5-dinitro-benzenesulphonamide (oryzalin),S-phenylmethylN,N-dipropyl-thiocarbamate(prosulfocarb),3-chloro 4-chloromethyl-1-(3-trifluoromethyl-phenyl)-pyrrolidin-2-one (fluorochloridone), 2-chloro-6-nitro-3-phenoxy-benzenamine (aclonifen), N'-(4-bromo-phenyl)-N -methoxy-N-methylurea (metobromuron), 9-hydroxy-9H-fluoren-9-carboxylic acid (flurenol), 7-chloro-3-methyl-quinoline-8-carboxylic acid (quinmerac), 4-hydroxy-3,5-diiodo-benzonitrile (ioxynil), N-(3-(1-ethyl-1-methyl-propyl) isoxazol-5-yl)-2,6-dimethoxy-benzamide (isoxaben), N'-(3-chloro-4-methoxy -phenyl)-N,N-dimethyl-urea (metoxuron), N-butyl-N'-(3,4-dichloro-phenyl)-N -methyl-urea (neburon), (4-chloro-2-methyl-phenoxy)-acetic acid (MCPA),2-(4-chloro-2-methyl-phenoxy)-propionic acid (mecoprop),3,5-dibromo-4-hydroxy-benzaldehyde O-(2,4-dinitro-phenyl) oxime (bromofenoxim), 4-chloro-2-oxo 3(2H)-benzothiazoleacetic acid (benazolin), 3,6-dichloro-pyridine-2-carboxylic acid (clopyralid), 2-(4-chloro-2-fluoro-5-(2-chloro-2-ethoxycarbonyl-ethyl) -phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one(F-8426), 1-(4-chloro-3-(2,2,3,3,3-pentafluoro-propoxymethyl)-phenyl)-5-phenyl-1H-1,2,4-triazole-3-carboxamide (flupoxam), 6-(6,7-dihydro-6,6-dimethyl-3H,5H-pyrrolo �2, 1-c!-1,2,4-thiadiazol-3-ylideneamino)-7-fluoro-4-(2-propinyl)-2H-1,4benzoxazin-3(4H)-one (thidiazimin), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(2cyclopropylcarbonyl-phenyl-sulphonyl)-urea (AC-322140), 4-chloro-3-(4-chloro -2-fluoro-5-ethoxycarbonyl-methoxy)-5-difluoromethoxy-1-methyl-pyrazole(ET-751), N-butoxymethyl-2-chloro-N-(2,6-diethyl-phenyl)-acetamide (butachlor), 2-chloro-N-(2,6-diethyl-phenyl)-N-(2-propoxy-ethyl)-acetamide (pretilachlor), S-(phenylmethyl) N-ethyl-N-(1,2-dimethyl-propyl-thiocarbamate (esprocarb), N-(4-methyl-phenyl)-N'-(1-methyl-1-phenyl-ethyl-urea (dymron), 4(2,4-dichloro-benzoyl)-1,3-dimethyl-5-(4-methyl-phenyl-sulphonyloxy)-pyrazole (pyrazolate), 4-(2,4-dichloro-benzoyl)-1,3-dimethyl-5-(phenyl-carbonylmethoxy) -pyrazole (pyrazoxyfen),N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N'-(2-(2-methoxy -ethoxy)-phenylsulphonyl)-urea (cinosulfuron), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(4-ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulphonyl)-urea (pyrazosulfuron-ethyl), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(2-chloro-imidazo�1,2-a!-pyridin-3-yl-sulphonyl)-urea (imazosulfuron), S,S-dimethyl 2-difluoromethyl-4-i-butyl-6-trifluoromethyl-pyridine-3,5-dicarbothioate (dithiopyr), 2-bromo-3,3-dimethyl-N -(1-methyl-1-phenyl-ethyl)-butanamide (bromobutide), 2-2-naphthyloxy)-N -phenyl-propanamide (naproanilide), 2-chloro-N-(2,6-dimethyl-phenyl)-N-(3-methoxy-2-thienyl-methyl)-acetamide (thenylchlor), 1,3,5-trichloro-2(4-nitro -phenoxy)-benzene(chlornitrofen),2,4-dichloro-1-(3-methoxy-4-nitro-phenoxy) -benzene (chlomethoxyfen) - ("active compounds of group 2") - and/or
- (c) a compound which improves the tolerance by crop plants, from the following group of compounds: a-(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil), a-(cyanomethoximino)-phenylacetonitrile(cyometrinil),4-chloro-N-(1,3-dioxolan -2-yl-methoxy)-a-trifluoro-acetophenone oxime (fluxofenim), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4benzoxazine (benoxacor),5-chloro-quinoxalin-8-oxy-acetic 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-dichloro -phenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazol-ethyl), 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid phenylmethyl ester (flurazole), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl -oxazolidine (furilazole, MON-13900), 4-dichloroacetyl-1-oxa-4-azaspiro�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-dichloro-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-trimethylpyrrolo�1,2-a!-pyrimidin-6(2H)-one (BAS-145138), N-(2-methoxy -benzoyl)-4-(methylaminocarbonylamino)-benzenesulphonamide - ("antidotes" or "safeners") -from 0.1 to 10 parts by weight of an active compound of group 2 and/or from 0.1 to 10parts by weight of one of the abovementioned antidotes/safeners being present per part by weight of an active compound of group 1 (i.e. of the formula (I)).
- 4. Selective-herbicidal compositions, characterized by a content of an active compound combination consisting of
- (a) a heteroaryloxy-acetamide of the general formula (I) according to claim 1, in which
- Het represents 1,2,4-thiadiazolyl or 1,3,4-thiadiazolyl, which is substituted by chlorine, dichloromethyl, difluoromethyl, trichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl or pentafluoroethyl, and
- Ar represents phenyl which is optionally substituted by fluorine, chlorine, methyl or trifluoromethyl,
- ("active compounds of group 1") and
- (b) one or two compounds from a second group of herbicides which contains the active compounds mentioned below: N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-chloro-4-methoxycarbonyl-1-methyl -pyrazol-5-yl-sulfonyl)-urea(clopyrasulfuron,halosulfuron,NC-319),2-chloro-N -(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methyl-ethyl)-acetamide (dimethenamid,SAN-582),2-chloro-N-(2,6-dimethyl-phenyl)-N-(1H-pyrazol-1-yl-methyl-acetamide (metazachlor), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(3-ethylsulfonyl-pyridin-2-yl-sulfonyl)-urea (rimsulfuron), 3-i-propyl-1H-2,1,3benzotrhiadiazin-4(3H)-one (bentazone), 3,5-dibromo-4-hydroxy-benzonitrile bromoxynil 3,6-dichloro-2-methoxybenzoic acid (dicamba), 2,4-dichloro phenoxyacetic acid (2,4-D), O-(6-chloro-3-phenyl-pyridazin-4-yl) S-octyl thiocarbonate(pyridate),(4-amino-3,5-dichloro-6-fluoro-pyridin-2-yl-oxy)-acetic acid (fluroxypyr), N-(2,6-difluoro-phenyl)-5-methyl-1,2,4-triazolo�1,5-a!pyrimidine -2-sulphonamide (flumetsulam, DE498), N-(2,6-dichloro-3-methyl -phenyl)-5,7-dimethoxy- 1,2,4-triazolo�1,5-a!-pyrimidine-2-sulphonamide (metosulam, DE511), N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-N'-(2-(3,3,3-trifluoropropyl-phenylsulphonyl)-urea(prosulfuron),5-(N-(4-chloro-2-fluoro-5-methoxycarbonylmethylthio-phenyl)-imino)-tetrahydro-3-oxo-1H,3H- 1,3,4-thiadiazolo�3,4-a!-pyridazine (KIH-9201), 2-(2-chloro-4-methylsulphonyl-benzoyl) cyclohexane-1,3-dione (sulcotrione), N'-(4-(3,4-dihydro-2-methoxy -2,4,4-trimethyl-2H-1-benzopyran-7-yl-oxy)-phenyl)-N-methoxy-N-methyl-urea (metobenzuron, UMP-488),3-amino-2,5-dichloro-benzoic acid (chloramben),2-(2-chloro-phenyl-methyl)-4,4-dimethyl-isoxazolidin-3-one (clomazone),2-(2,4-dichloro-5-methylsulphonylamino-phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (sulfentrazone, F6285),2-(4,5,-dihydro-4-methyl -4-i-propyl-5-oxo-1H-imidazol-2-yl)-5-ethyl-pyridine-3-carboxylic acid (imazethapyr), 2-(4,5-dihydro-4-methyl-4-i-propyl-5-oxo-1H-imidazol-2-yl)-5methyl-pyridine-3-carboxylic acid (imazamethapyr), 5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoic acid ethoxycarbonylmethyl ester (fluoroglycofen-ethyl), 4-dipropylamino-3,5-dinitro-benzenesulphonamide (oryzalin),S-phenylmethylN,N-dipropyl-thiocarbamate(prosulfocarb),3-chloro -4-chloromethyl-1-(3-trifluoromethyl-phenyl)-pyrrolidin-2-one (fluorochloridone), 2-chloro-6-nitro-3-phenoxy-benzenamine (aclonifen), N'-(4bromo-phenyl)-N -methoxy-N-methylurea (metobromuron), 9-hydroxy-9H-fluoren-9-carboxylic acid (flurenol), 7-chloro-3-methyl-quinoline-8-carboxylic acid (quinmerac), 4hydroxy-3,5-diiodo-benzonitrile (ioxynil), N-(3-(1-ethyl-1-methyl-propyl) -isoxazol-5-yl)-2,6-dimethoxy-benzamide (isoxaben), N'-(3-chloro-4-methoxy -phenyl)-N,N-dimethyl-urea (metoxuron), N-butyl-N'-(3,4-dichloro-phenyl)-N-methyl-urea (neburon), (4-chloro-2-methyl-phenoxy)-acetic acid MCPA), 2-(4-chloro-2-methyl-phenoxy)-propionic acid (mecoprop), 3,5-dibromo-4-hydroxy -benzaldehyde O-(2,4-dinitro-phenyl oxime (bromofenoxim), 4-chloro-2-oxo- -3(2H)-benzothiazoleacetic acid (benazolin), 3,6-dichloro-pyridine-2-carboxylic acid (clopyralid), 2-(4-chloro-2-fluoro-5-(2-chloro-2-ethoxycarbonyl-ethyl) -phenyl)-4-difluoromethyl-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-(one(F-8426), 1-(4-chloro-3-(2,2,3,3,3,-pentafluoro-propoxymethyl)-phenyl-1H-1,2,4-triazole-3-carboxamide (flupoxam), 6-(6,7-dihydro-6,6-dimethyl-3H,5H-pyrrolo �2,1-c!-1,2,4-thiadiazol-3ylideneamino)-7-fluoro-4-(2-propinyl)-2H-1,4benzoxazin-3(4H)-one (thiadiazimin), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(2-cyclopropylcarbonyl-phenyl-sulphonyl)-urea (AC-322140), 4-chloro-3-(4-chloro 2-fluoro-5-ethoxycarbonyl-methoxy)-5-difluoromethoxy-1-methyl-pyrazole(ET-751), N-butoxymethyl-2-chloro-N-(2,6-diethyl-phenyl)-acetamide(butachlor),2-chloro-N-(2,6-diethyl-phenyl)-N-(2-propoxy-ethyl)-acetamide (pretilachlor), S-(phenylmethyl) N-ethyl-N-(1,2-dimethyl-propyl)-thiocarbamate (esprocarb), N-(4-methyl-phenyl)-N'-(1-methyl-1-phenyl-ethyl)-urea (dymron), 4-(2,4-dichloro-benzoyl)-1,3-dimethyl-5-(4-methyl-phenyl-sulphonyloxy)-pyrazole (pyrazolate), 4-(2,4-dichloro-benzoyl)-1,3-dimethyl-5-(phenyl-carbonylmethoxy)-pyrazole (pyrazoxyfen),N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N'-(2-(2-methoxy -ethoxy)-phenylsulphonyl)-urea (cinosulfuron), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(ethoxycarbonyl-1-methyl-pyrazol-5-yl-sulphonyl)-urea (pyrazosulfuron-ethyl), N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(2-chloro-imidazo�1,2-a!-pyridin-3-yl-sulphonyl)-urea (imazosulfuron), S.S-dimethyl 2-difluoromethyl-4-i-butyl-6-trifluoromethyl-pyridine-3,5-dicarbothioate (dithiopyr), 2-bromo-3,3-dimethyl-N -(1-methyl-1-phenyl-ethyl)-butanamide (bromobutide), 2-(2-naphthyloxy)-N-phenyl-propanamide (naproanilide), 2-chloro-N-(2,6-dimethyl-phenyl)-N-(3-methoxy-2-thienyl-methyl)-acetamide (thenylchlor), 1,3,5-trichloro-2-(4-nitro -phenoxy)-benzene (chlornitrofen),2,4-dichloro-1-(3-methoxy-4-nitro-phenoxy)-benzene (chlomethoxyfen) - ("active compounds of group 2").
- 5. Selective herbicidal compositions, characterized by a content of an active compound combination consisting of
- (a) a heteroaryloxy-acetamide of the general formula (I) according to claim 1, in which
- Het represents 1,2,4-thiadiazolyl or 1,3,4-thiadiazolyl, which is substituted by chlorine, dichloromethyl, difluoromethyl, trichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl or pentafluoroethyl, and
- Ar represents phenyl which is optionally substituted by fluorine, chlorine, methyl or trifluoromethyl,
- ("active compounds of group 1") and
- (b) a compound which improves the tolerance by crop plants, from the following group of compounds: a -(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil), a-(cyanomethoximino)-phenylacetonitrile(cyometrinil),4-chloro-N-(1,3-dioxolan 2-yl-methoxy)-a-trifluoro-acetophenone oxime (fluxofenim), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4benzoxazine (benoxacor), 5-chloro-quinoxalin-8-oxy-acetic 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-dichloro -phenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylic acid ethyl ester (fenchlorazol-ethyl), 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acid phenylmethyl ester (flurazole), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl -oxazolidine (furilazole, MON-13900), 4-dichloroacetyl-1-oxa-4azaspiro�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-dichloro-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-trimethylpyrrolo�1,2-a!-pyrimidin-6(2H)-one (BAS-145138), N-(2-methoxy -benzoyl)-4-(methylaminocarbonylamino)-benzenesulphonamide - ("antidotes" or "safeners").
- 6. Selective-herbicidal compositions according to claim 4, characterized in that, in the active compound combinations, the weight ratio of the active compound of the formula (I) to the active compound/s of group 2 is between 1:0.01 and 1:100.
- 7. Selective-herbicidal compositions according to claim 5, characterized in that, in the active compound combinations, the weight ratio of active compound of the formula (I) to the antidote/safener is between 1:0.01 and 1:100.
- 8. Method for the selective combating of weeds, characterized in that an active compound combination according to claim 1 is allowed to act on weeds or their habitat.
- 9. The composition according to claim 1, wherein the active compound combination consists of
- (a) N-i-propyl-N-(4-fluoro-phenyl)-alpha-(5-trifluoromethyl- 1,3,4-thiadiazol-2-yl-oxy)-acetamide (l-1); and
- (b) N-(2,6-dichloro-3-methyl-phenyl)-5,7-dimethoxy-1,2,4-triazolo�1,5-a!-pyrimidine-2-sulphonamide (metosulam, DE 511).
Priority Claims (1)
Number |
Date |
Country |
Kind |
44 46 341.3 |
Dec 1994 |
DEX |
|
Parent Case Info
This application is a division, of application Ser. No. 08/573,804, filed Dec. 18, 1995, abandoned.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
4988380 |
Forster et al. |
Jan 1991 |
|
5502025 |
Bussler |
Mar 1996 |
|
5593942 |
Santel et al. |
Jan 1997 |
|
Foreign Referenced Citations (2)
Number |
Date |
Country |
3418167 |
Nov 1985 |
DEX |
9402014 |
Feb 1994 |
WOX |
Non-Patent Literature Citations (1)
Entry |
Hopkins, William L. Global Herbicide Directory, 1st Ed. "Eclipse, Uptake, metosulam, DE-511". Ag Chem Information Services: Indianapolis, Indiana. p. 48, 1994. |
Divisions (1)
|
Number |
Date |
Country |
Parent |
573804 |
Dec 1995 |
|