Selective heteroaryloxy-acetamide-based herbicides

Abstract

The invention relates to novel herbicidal synergistic active compound combinations comprising heteroaryloxy-acetamides and known herbicidally active compounds and/or safeners listed in the description, which active compound combinations can be used with particularly good results for the selective control of weeds in crops of various useful plants.

1 - 10 . (canceled)  
     
     
         11 . A composition comprising an herbicidally effective amount of an active compound combination consisting of 
 (a) a heteroaryloxy-acetamide of the formula (I)                        in which    Ar represents optionally halogen-, C 1 -C 4 -alkyl-, or C 1 -C 4 -halogenoalkyl-substituted phenyl,    Het represents thiadiazolyl that is substituted by halogen or by optionally halogen-substituted C 1 -C 4 -alkyl or phenyl, and    R represents alkyl, alkenyl, or alkynyl having in each case up to 4 carbon atoms,      (b) one or more herbicidally active compounds, other than the heteroaryloxy-acetamide of the formula (I), selected from the group consisting of 1H-1,2,4-triazol-3-amine (amitrole), 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-(4,6-dimethoxy-pyrimidin-2-yl)-N′-[1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazol-5-ylsulphonyl]urea (azimsulfuron), N-benzyl-2-(4-fluoro-3-trifluoromethyl-phenoxy)butanamide (beflubutamid), N-butyl-N-ethyl-2,6-dinitro-4-trifluoro-methyl-benzeneamine (benfluralin), methyl 2-[2-[4-(3,6-dihydro-3-methyl-2,6-dioxo-4-trifluoromethyl-1 (2H)-pyrimidinylphenoxymethyl]-5-ethyl-phenoxy-propanoate (benzfendizone), 3-(2-chloro-4-methylsulphonyl-benzoyl)-4-phenylthio-bicyclo[3.2.1]oct-3-en-2-one (benzobicyclon), 2-(1-ethoximino-propyl)-3-hydroxy-5-[2,4,6-trimethyl-3-(1-oxo-butyl)phenyl]-2-cyclohexen-1-one (butroxydim), 2-[1-[(3-chloro-2-propenyl)-oxy-imino]propyl]-3-hydroxy-5-(tetrahydro-2H-pyran-4-yl)-2-cyclohexen-1-one (caloxydim, tepraloxydim), 2-[1-[2-(4-chloro-phenoxy)]propoxyaminobutyl]-5-(tetrahydro-2H-thiopyran-3-yl)-1,3-cyclohexanedione (clefoxydim), (E,E)-(+)-2-[1-[[(3-chloro-2-propenyl)-oxy]imino]propyl]-3-hydroxy-2-cyclohexen-1-one (clethodim), methyl 3-chloro-2-[[(5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)sulphonyl]amino]-benzoate (cloransulam-methyl), 2-(1-ethoximinobutyl)-3-hydroxy-5-(tetrahydro-2H-thiopyran-3-yl)-2-cyclohexen-1-one (cycloxydim), N-(2,6-dichloro-phenyl)-5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine-2-sulphonamide (diclosulam), 2-[1-[(3,5-difluorophenyl)aminocarbonyl-hydrazono]ethyl]-pyridine-3-carboxylic acid (diflufenzopyr), 2-[2-(3-chlorophenyl)oxiranyl-methyl]-2-ethyl-1H-indene-1,3(2H)-dione (epropodan), ethyl[2-chloro-4-fluoro-5-(5-methyl-6-oxo-4-trifluoromethyl-1 (6H)-pyridazinyl)phenoxy]acetate (flufenpyr), 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]-sulphonyl]-4-formylamino-N,N-dimethyl-benzamide (foramsulfuron), 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl)-5-(methoxy-methyl)-3-pyridinecarboxylic acid (imazamox), (4-chloro-2-methylsulphonyl-phenyl)(5-cyclopropyl-isoxazol-4-yl)methanone (isoxachlortole), methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulphonyl]-4-[[(methylsulphonyl)amino]methyl]benzoate (mesosulfuron), 3-[1-(3,5-dichlorophenyl)-1-i-propyl]-2,3-dihydro-6-methyl-5-phenyl-4H-1,3-oxazin-4-one (oxaziclomefone), 2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy[1,2,4]triazolo-[1,5-c]pyrimidin-2-yl)-6-trifluoromethylbenzenesulphonamide (penoxsulam), 2-chloro-N-(2-ethoxyethyl)-N-(2-methyl-1-phenyl-1-propenyl)acetamide (pethoxamid), 1-chloro-N-[2-chloro-4-fluoro-5-[(6S,7aR)-6-fluoro-tetrahydro-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl]phenyl]methanesulphonamide (profluazol), (R)-[2-[[(1-methyl-ethylidene)amino]oxy]ethyl]2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]propanoate (propaquizafop), 2-chloro-N-(2-ethyl-6-methyl-phenyl)-N-[(1-methylethoxy)methyl]acetamide (propisochlor), 1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-5-(methyl-2-propynyl-amino)-1H-pyrazol-4-carbonitrile (pyraclonil), ethyl[2-chloro-5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-4-fluorophenoxy]acetate (pyraflufen-ethyl), 6-chloro-3-phenyl-pyridazin-4-ol (pyridatol), 7-[(4,6-dimethoxy-2-pyrimidinyl)thio]-3-methyl-[(3H)-isobenzofuranone (pyriftalide), methyl 2-(4,6-dimethoxy-pyrimidin-2-yl-oxy)benzoate (pyriminobac-methyl), the sodium salt of 2-chloro-6-(4,6-dimethoxypyrimidin-2-ylthio)benzoate (pyrithiobac-sodium), methyl 2-difluoromethyl-5-(4,5-dihydrothiazol-2-yl)-4-(2-methylpropyl)-6-trifluoromethyl-pyridine-3-carboxylate (thiazopyr), (3,5,6-trichloro)pyridin-2-yl-oxyacetic acid (triclopyr), the sodium salt of N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(2,2,2-trifluoroethoxy)-2-pyridinesulphonamide (trifloxysulfuron), N-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]-N′-(2-methoxycarbonylphenylsulphonyl)urea (triflusulfuron-methyl), and N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(N-methyl-N-methylsulphonyl-amino])-2-pyridinesulphonamide, and    (c) optionally, a compound that improves crop plant tolerance selected from the group consisting of 4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]decane (AD-67), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)-one (dicyclonon, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 1-methyl hexyl 5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl), α-(cyanomethoximino)phenylacetonitrile (cyometrinil), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)ethyl)-N-(2-propenyl)acetamide (DKA-24), 2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid), N-(4-methylphenyl)-N′-(1-methyl-1-phenylethyl)urea (dymron), 4,6-dichloro-2-phenylpyrimidine (fenclorim), ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazol-ethyl), phenylmethyl 2-chloro-4-trifluoromethyl-thiazole-5-carboxylate (flurazole), 4-chloro-N-(1,3-dioxolan-2-yl-methoxy)-α-trifluoroacetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), diethyl-1-(2,4-dichloro-phenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 1,8-naphthalene-dicarboxylic anhydride, α-(1,3-dioxolan-2-yl-methoximino)phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-yl-methyl)-N-(2-propenyl)acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148), methyl 1-(2-chloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate, and N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulphonamide.    
     
     
         12 . A composition according to  claim 11  wherein, in the formula (I), 
 Ar represents optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, or trifluoromethyl-substituted phenyl,    Het represents 1,2,4-thiadiazolyl or 1,3,4-thiadiazolyl substituted by fluorine, chlorine, bromine or by in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, or phenyl, and    R represents methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, 2-propenyl, 1-methyl-2-propenyl, 2-butenyl, 2-propynyl, 1-methyl-2-propynyl, or 2-butynyl.    
     
     
         13 . A composition according to  claim 11  wherein the heteroaryloxy-acetamide of formula (I) is N-i-propyl-N-(4-fluoro-phenyl)-α-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy)acetamide.  
     
     
         14 . A composition according to  claim 11  wherein the herbicidally active compounds of component (b) are selected from the group consisting of azimsulfuron, beflubutamid, clefoxydim, cloransulam-methyl, diclosulam, foramsulfuron, imazamox, isoxachlortole, mesosulfuron, oxaziclomefone, pyriftalid, pyrithiobac-sodium, and trifloxysulfuron.  
     
     
         15 . A composition according to  claim 11  wherein the heteroaryloxy-acetamide of formula (I) is N-i-propyl-N-(4-fluoro-phenyl)-α-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl-oxy)acetamide and the herbicidally active compound of component (b) is mesosulfuron.  
     
     
         16 . A composition according to  claim 11  wherein the compounds of component (c) that improve crop plant tolerance are selected from group consisting of 1-methyl-hexyl 5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl), 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), 4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]decane (AD-67), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]pyrimidin-6(2H)-one (BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 2,2-dichloro-N,N-di-2-propenylacetamide (dichlormid), 2,2-dichloro-N-(2-oxo-2-(2-propenyl-amino)ethyl)-N-(2-propenyl)acetamide (DKA-24), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (furilazole, MON-13900), and 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148).  
     
     
         17 . A composition according to  claim 11  wherein from 0.01 to 1000 parts by weight of the herbicidally active compounds of component (b) are used per part by weight of the heteroaryloxy-acetamide of formula (I).  
     
     
         18 . A composition according to  claim 11  wherein from 0.001 to 1000 parts by weight of one or more compounds of component (c) that improve crop plant tolerance are used per part by weight of the heteroaryloxy-acetamide of formula (I) or a mixture thereof with an herbicidally active compound of component (b).  
     
     
         19 . A method for controlling undesirable plants comprising allowing a composition according to  claim 11  to act on the undesirable plants and/or their habitat.  
     
     
         20 . A process for preparing an herbicidal composition comprising mixing a composition according to  claim 11  with surfactants and/or extenders.