Herbicidal mixtures

Abstract

A synergistic herbicidal mixture comprising A) picolinafen; or one of its environmentally compatible salts; and B) a synergistically effective amount of at least a sulfonylurea of formula II, wherein the variables A, B, X and R 1 to R 3 have the meanings given in the specification; and, if desired, C) at least a safener. Compositions comprising these mixtures, processes for the preparation of these compositions and their use for controlling undesired plants.

1 . A synergistic herbicidal mixture comprising 
 A) picolinafen (I)                          or one of its environmentally compatible salts; and    B) a synergistically effective amount of at least one sulfonylurea of formula II                          wherein    A is A1, A2, A3, A4 or A5                          wherein 
 R 4  is halogen, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 2 -alkoxy-C 1 -C 4 -alkoxy, cyclopropylcarbonyl, di(C 1 -C 4 -alkyl)-aminocarbonyl or hydroxycarbonyl;  
 R 5  is hydrogen, halogen or C 1 -C 4 -alkylsulfonylamino-C 1 -C 4 -alkyl;  
 R 6  is hydroxycarbonyl or C 1 -C 4 -alkylsulfonyl;  
 R 7  is hydrogen or C 1 -C 4 -haloalkyl;  
 R 8  is hydroxycarbonyl;  
 R 9  is 2-methyl-tetrazol-5-yl or hydroxycarbonyl;  
 R 10  is hydrogen or halogen;  
 R 11  is C 1 -C 4 -alkyl;  
 R 12  is halogen or C 1 -C 4 -alkylsulfonyl;  
   B is —O—, —NH—, —CH 2 — or a bond;    R 1  is hydrogen or C 1 -C 4 -alkyl;    R 2  is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalk-oxy, C 1 -C 4 -alkylamino or di(C 1 -C 4 -alkyl)amino;    R 3  is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy or C 1 -C 4 -alkoxy;    X is CH or N;    or one of its environmentally compatible salts or esters; and, if desired,    C) at least a safener selected from the group consisting of dichlormid, benoxacor, LAB 145 138, MG-191, furilazole, cyometrinil, oxabetrinil, fluxofenim, flurazole, naphthalic acid anhydride, fenclorim, fenchlorazole-ethyl, mefenpyr, isoxa-difen, cloquintocet, 1 -ethyl-4-hydroxy-3(1H-tetrazol-5-yl)-1H-quinolin-2-one, 4-carboxymethyl-chroman-4-carboxylic acid, N-(2-methoxybenzyl)-4-(3-methylureido)-benzenesulfonamide and (3-oxo-isothio-chroman-4-ylidenmethoxy)acetic acid methyl ester;    or an environmentally compatible salt, ester or amide thereof.    
   
   
       2 . A synergistic herbicidal mixture as claimed in  claim 1  comprising, as component B) at least one sulfonylurea of formula II, wherein 
 A is A1, wherein 
 R 4  is halogen, C 1 -C 3 -haloalkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -halo-alkoxy, C 1 -C 2 -alkoxy-C 1 -C 2 -alkoxy cyclopropylcarbonyl, di(C 1 -C 2 -alkyl)amino-carbonyl, hydroxycarbonyl or methoxycarbonyl, ethoxycarbonyl or oxetan-3-yloxycarbonyl;  
 R 5  is hydrogen, halogen, or C 1 -C 2 -alkylsulfonylamino-C 1 -C 2 -alkyl;  
   R 1  is hydrogen; or C 1 -C 2 -alkyl;    R 2  is halogen, C 1 -C 2 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -haloalkoxy, C 1 -C 2 -alkylamino, or di(C 1 -C 2 -alkyl)-amino;    R 3  is C 1 -C 2 -alkyl, C 1 -C 3 -alkoxy, or C 1 -C 2 -haloalkoxy;    X is CH or N;    or one of its environmentally compatible salts;    
   
   
       3 . A synergistic herbicidal mixture as claimed in  claim 1  comprising, as a component B) at least one sulfonylurea of formula II, wherein 
 A is A2, wherein 
 R 6  is C 1 -C 2 -alkylsulfonyl, hydroxycarbonyl or methoxycarbonyl;  
 R 7  is hydrogen or C 1 -C 2 -haloalkyl;  
   B is a bond;    R 1  is hydrogen;    R 2  is C 1 -C 2 -alkoxy;    R 3  is C 1 -C 2 -alkoxy;    X is CH;    or one of its environmentally compatible salts;    
   
   
       4 . A synergistic herbicidal mixture as claimed in  claim 1  comprising, as component B) at least one sulfonylurea of formula II wherein 
 A is A3, wherein 
 R 8  is hydroxycarbonyl or methoxycarbonyl;  
   B is a bond;    R 1  is hydrogen;    R 2  is C 1 -C 2 -alkyl;    R 3  is C 1 -C 2 -alkoxy;    X is CH;    or one of its environmentally compatible salts.    
   
   
       5 . A synergistic herbicidal mixture as claimed in  claim 1  comprising, as component B) at least one sulfonylurea of formula II wherein 
 A is A4, wherein 
 R 9  is 2-methyl-tetrazol-5-yl, hydroxycarbonyl, methoxycarbonyl or ethoxycarbonyl;  
 R 10  is hydrogen, or halogen;  
 R 11  is C 1 -C 2 -alkyl;  
   B is a bond;    R 1  is hydrogen;    R 2  is C 1 -C 2 -alkoxy;    R 3  is C 1 -C 2 -alkoxy;    X is CH;    or one of its environmentally compatible salts.    
   
   
       6 . A synergistic herbicidal mixture as claimed in  claim 1  comprising, as component B) at least one sulfonylurea of formula II wherein 
 A is A5, wherein 
 R 12  is halogen , preferably chlorine; or C 1 -C 2 -alkyl-sulfonyl;  
   B is a bond;    R 1  is hydrogen;    R 2  is C 1 -C 2 -alkoxy;    R 3  is C 1 -C 2 -alkoxy;    X is CH;    or one of its environmentally compatible salts.    
   
   
       7 . A synergistic herbicidal mixture as claimed in  claim 1  comprising, as component B) at least one sulfonylurea selected from the group consisting of azimsulfuron, bensulfuron, chlorimuron, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethoxysulfuron, flazasulfuron, flupyrsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metsulfuron, nicosulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, triflusulfuron, trifloxysulfuron and tritosulfuron, or an environmentally compatible salts or esters thereof.  
   
   
       8 . A synergistic herbicidal mixture as claimed in  claim 1  comprising, as component B) at least one sulfonylurea selected from the group consisting of azimsulfuron, bensulfuron, chlorimuron, chlorsulfuron, cyclosulfamuron, ethametsulfuron, ethoxysulfuron, flazasulfuron, flupyrsulfuron, halosulfuron, imazosulfuron, metsulfuron, nicosulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, triflusulfuron, trifloxysulfuron and tritosulfuron, or an environmentally compatible salt or ester thereof.  
   
   
       9 . A synergistic herbicidal mixture as claimed in  claim 1  comprising, as component B) at least one sulfonylurea selected from the group consisting of azimsulfuron, bensulfuron, chlorimuron, chlorsulfuron, cyclosulfamuron, ethametsulfuron, ethoxysulfuron, flazasulfuror, halosulfuron, imazosulfuron, nicosulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, triasulfuron and triflusulfuron, or an environmentally compatible salt or ester thereof.  
   
   
       10 . A synergistic herbicidal mixture as claimed in  claim 1  comprising, as component B) at least one sulfonylurea selected from the group consisting of chlorsulfuron, flupyrsulfuron, iodosulfuron, mesosulfuron, metsulfuron, prosulfuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, and tritosulfuron, or an environmentally compatible salt or ester thereof.  
   
   
       11 . A synergistic herbicidal mixture as claimed in  claim 1  comprising, as component B) at least one sulfonylurea selected from the group consisting of chlorsulfuron, flupyrsulfuron, metsulfuron, prosulfuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, and tritosulfuron, or an environmentally compatible salt or ester thereof.  
   
   
       12 . A synergistic herbicidal mixture as claimed in  claim 1  comprising, as component B) at least one sulfonylurea selected from the group consisting of chlorsulfuron, prosulfuron and triasulfuron, or an environmentally compatible salt or ester thereof.  
   
   
       13 . A synergistic herbicidal mixture as claimed in  claim 1  comprising, as component C) cloquintocet, isoxadifen or mefenpyr.  
   
   
       14 . A synergistic herbicidal mixture as claimed in  claim 1 , additionally comprising as component D) an acetyl-CoA carboxylase inhibitor (ACC), acetolactate synthase inhibitor (ALS), amide, auxin herbicide, auxin transport inhibitor, carotenoid biosynthesis inhibitor, enolpyruvylshikimate 3-phosphate synthase inhibitor (EPSPS), glutamine synthetase inhibitor, lipid biosynthesis inhibitor, mitosis inhibitor, protoporphyrinogen IX oxidase inhibitor, photosynthesis inhibitor, synergist, growth substance, cell wall biosynthesis inhibitor or another herbicide.  
   
   
       15 . A synergistic herbicidal mixture as claimed in  claim 1  comprising as active ingredients only picolinafen and one compound of group B).  
   
   
       16 . A synergistic herbicidal mixture as claimed in  claim 1  comprising as active ingredients only picolinafen, one compound of group B) and one compound of group C).  
   
   
       17 . A synergistic herbicidal mixture as claimed in  claim 1  wherein the ratios of the compounds of the groups A) and B) range from 1:0.0002 to 1:50.  
   
   
       18 . A synergistic herbicidal mixture as claimed in  claim 1  wherein the ratios of the compounds of the groups A) and C) range from 1:0.0002 to 1:50.  
   
   
       19 . A herbicidal composition comprising a herbicidally active amount of a synergistic herbicidal mixture as claimed in  claim 1 , at least one liquid and/or solid carrier and, if desired, at least one surfactant.  
   
   
       20 . A process for the preparation of a herbicidal composition as claimed in  claim 18 , comprising mixing the compounds of group A), B), if desired, C), if desired, D), at least one liquid and/or solid carrier and, if desired, at least one surfactant.  
   
   
       21 . A method for controlling undesired vegetation, which comprises applying to undesired plants a synergistic herbicidal mixture as claimed in  claim 1 , during and/or after the emergence of the undesired plants, it being possible for the active compounds of the groups A), B), if desired, C) and, if desired D) to be applied simultaneously or in succession.  
   
   
       22 . A method for controlling undesired vegetation comprising simultaneously or successively applying to undesired plants, their habitation or their seeds 
 A) picolinafen (I)                          or one of its environmentally compatible salts; and    B) a synergistically effective amount of at least one sulfonylurea of formula 11                          wherein    A is A1, A2, A3, A4 or A5                          wherein 
 R 4  is halogen, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 2 -alkoxy-C 1 -C 4 -alkoxy, cyclopropylcarbonyl, di(C 1 -C 4 -alkyl)-aminocarbonyl or hydroxycarbonyl;  
 R 5  is hydrogen, halogen or C 1 -C 4 -alkylsulfonylamino-C 1 -C 4 -alkyl;  
 R 6  is hydroxycarbonyl or C 1 -C 4 -alkylsulfonyl;  
 R 7  is hydrogen or C 1 -C 4 -haloalkyl;  
 R 8  is hydroxycarbonyl;  
 R 9  is 2-methyl-tetrazol-5-yl or hydroxycarbonyl;  
 R 10  is hydrogen or halogen;  
 R 11  is C 1 -C 4 -alkyl;  
 R 12  is halogen or C 1 -C 4 -alkylsulfonyl;  
   B is —O—, —NH—, —CH 2 — or a bond;    R 1  is hydrogen or C 1 -C 4 -alkyl;    R 2  is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalk-oxy, C 1 -C 4 -alkylamino or di(C 1 -C 4 -alkyl)amino;    R 3  is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy or C 1 -C 4 -alkoxy;    X is CH or N;    or one of its environmentally compatible salts or esters; and, if desired,    C) at least a safener selected from the group consisting of dichlormid, benoxacor, LAB 145 138, MG-191, furilazole, cyometrinil, oxabetrinil, fluxofenim, flurazole, naphthalic acid anhydride, fenclorim, fenchlorazole-ethyl, mefenpyr, isoxa-difen, cloquintocet, 1-ethyl-4-hydroxy-3(1H-tetrazol-5-yl)-1H-quinolin-2-one, 4-carboxymethyl-chroman-4-carboxylic acid, N-(2-methoxybenzyl)-4-(3-methylureido)-benzenesulfonamide and (3-oxo-isothio-chroman-4-ylidenmethoxy)acetic acid methyl ester;    or one of its environmentally compatible salts, esters or amides.