Selective herbicidal composition

Abstract

A mixture of a herbicidally effective amount of a haloacetamide of formula I wherein R 0 is methyl or ethyl, and to antagonise the herbicide, an antidotally effective amount of a compound of formula II as safener R—CHYCl  (I) wherein R is a radical of formula or R is a radical of formula or R is a radical of formula or R is a radical of formula or R is a radical of formula or R is a radical of formula (H 5 C 2 O) 2 P(O)CH 2 NHCO— or (P—X) n R 25 or R is a radical of formula or of formula in each of which formulae the substituents are as defined in claim 1 and Y is chloro, or Y is hydrogen if R is a radical of formula (H 5 C 2 O) 2 P(O)CH 2 NHCO—, are very suitable for controlling weeds in crops of cultivated plants, in particular maize.

What is claimed is:  
     
         1 . A composition for the selective control of weeds in crops of cultivated plants, comprising, in addition to inert carriers and adjuvants, as active component, a mixture of 
 a) a herbicidally effective amount of a compound of formula I                          wherein R 0  is methyl or ethyl, and    b) to antagonise the herbicide, an antidotally effective amount of a compound of formula II as safener    R—CHYCl  (II)    wherein R is a radical of formula                          wherein    R 33  and R 34  are each independently of the other C 1 -C 6 alkyl or C 2 -C 6 alkenyl; or R 33  and R 34 , taken together, are                          R 35  and R 36  are each independently of the other hydrogen or C 1 -C 6 alkyl;    or R 33  and R 34 , taken together, are                          R 37  and R 38  are each independently of the other C 1 -C 4 alkyl, or R 37  and R 38 , taken together, are —(CH 2 ) 5 —;    —R 39  is hydrogen, C 1 -C 4 alkyl or                          or R 33  and R 34 , taken together, are                          or                          and R 40 , R 41 , R 42 , R 43 , R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 , R 54  and R 55  are each independently of one another hydrogen or C 1 -C 4 alkyl,    or R is a radical of formula                          or                          or R is a radical of formula                          wherein R 1 , R 2 , R 3  and R 4  are each independently of one another hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkyl, R 5 , R 6 , R 7  and R 8  are each independently of one another hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, or R is a radical of formula                          wherein R 9  is C 1 -C 4 alkyl or halogen, R 10  is halogen, R 11  and R 12  are each independently of the other hydrogen or C 1 -C 4 alkyl, and Q is C 1 -C 4 alkylene or alkyl-substituted C 1 -C 4 alkylene,    or R is a radical of formula                          wherein R 14  is hydrogen, halogen, C 1 -C 4 alkyl, dioxymethylene, C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy or cyano-C 1 -C 4 alkyl, P is C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 8 cycloalkyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 2 -C 4 alkenoxy-C 1 -C 4 alkyl, C 2 -C 4 alkynoxy-C 1 -C 4 alkyl, C 1 -C 4 alkylthio-C 1 -C 4 alkyl, C 2 -C 4 alkenylthio-C 1 -C 4 alkyl, C 2 -C 4 alkynylthio-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkyl, halo-C 1 -C 4 alkyl, cyano-C 1 -C 4 alkyl, 2,2-di-C 1 -C 4 alkoxy-C 1 -C 4 alkyl, 1,3-dioxolan-2-yl-C 1 -C 4 alkyl, 1,3-dioxolan-4-yl-C 1 -C 4 alkyl, 2,2-di-C 1 -C 4 alkyl-1,3-dioxolan-4-yl-C 1 -C 4 alkyl, 1,3-dioxan-2-yl-C 1 -C 4 alkyl, 2-benzopyranyl-C 1 -C 4 alkyl, C 1 -C 4 alkoxycarbonyl or C 2 -C 4 alkenyloxycarbonyl or tetrahydrofurfuryl-C 1 -C 4 alkyl, the group P—X is also halo-C 1 -C 4 alkyl, X is O, S, SO or SO 2 , n is 1, 2 or 3, A is a C 1 -C 8 hydrocarbon radical or a C 1 -C 8 hydrocarbon radical which is substituted by alkoxy, alkylthio, fluoro, cyano or haloalkyl, and R 13  is hydrogen, a C 1 -C 5 hydrocarbon radical or a C 1 -C 5 hydrocarbon radical which is substituted by alkoxy, polyalkoxy, halogen, cyano or trifluoromethyl; C 3 -C 8 cycloalkyl, C 1 -C 4 alkyl-C 3 -C 8 cycloalkyl, di-C 1 -C 4 alkoxy-C 1 -C 4 alkyl, 1,3-dioxolan-2-yl-C 1 -C 4 alkyl, 1,3-dioxolan-4-yl-C 1 -C 4 alkyl, 1,3-dioxan-2-yl-C 1 -C 4 alkyl, furyl-C 1 -C 4 alkyl, tetrahydrofuryl-C 1 -C 4 alkyl, or a radical of formula —NHCO 2 R 01 , —CH 2 CO 2 R 01 , —CH(CH 3 )CO 2 R 01 , or —CH(R 02 )—C(R 03 )═NOR 04 , wherein R 01  is methyl, ethyl, propyl, isopropyl or allyl, R 02  and R 03  are each hydrogen or C 1 -C 4 alkyl, and R 04  is hydrogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl or C 2 -C 4 alkynyl,    or R is a radical of formula (H 5 C 2 O) 2 P(O)CH 2 NHCO— or                          R15 R 5 P(O)CR1 7 R 8 N(NR 19 R 20 )co 7P(°)CR17R18N(NR19R20)C°   wherein R 15  and R 16  are each independently of the other hydroxyl, C 1 -C 4 alkyl, aryl, C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 2 -C 4 haloalkoxy, C 2 -C 8 alkoxyalkoxy, C 1 -C 4 cyanoalkoxy, C 1 -C 4 phenylalkoxy or aryloxy or aryloxy which is substituted by halogen, cyano, nitro or C 1 -C 4 alkoxy, R 17  is hydrogen, C 1 -C 4 alkyl or phenyl, or phenyl which is substituted by halogen, cyano, nitro or C 1 -C 4 alkoxy, R 18  is hydrogen, or C 1 -C 4 alkyl, R 19  is hydrogen or a radical of formula —COCX 1 X 2 —R 06 , or an alkenoyl radical which contains 2 to 4 carbon atoms in the alkenyl moiety and which is substituted by halogen, and X 1  and X 2  are each independently of the other hydrogen or halogen, or is a radical of formula —COOR 07  or —COR 08  or a C 1 -C 4 alkyl, C 2 -C 4 alkenyl or C 1 -C 4 phenylalkyl radical which may be substituted at the phenyl ring by halogen, cyano, nitro or C 1 -C 4 alkoxy, and R 20  is hydrogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl or C 2 -C 4 alkynyl, R 06  is hydrogen, halogen or C 1 -C 6 alkyl, R 07  is C 1 -C 4 alkyl, C 1 -C 4 phenylalkyl or C 1 -C 4 phenylalkyl which is substituted in the phenyl moiety by halogen, cyano, nitro or C 1 -C 4 alkoxy, and R 08  is C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, phenyl, C 1 -C 4 phenylalkyl or C 1 -C 4 phenylalkyl which is substituted in the phenyl moiety by halogen, cyano, nitro or C 1 -C 4 alkoxy,    or R is a radical of formula                          or of formula                          wherein R 21  is methyl, ethyl, propyl, 1-methylethyl, 2-propenyl, 2-butenyl, 1,1-dimethyl-2-propenyl, 2-propynyl or 2-methyl-2-propynyl, and R 22 , R 23 , R 24  and R 25  are each independently of one another hydrogen or methyl,    and Y is chloro, or    Y is hydrogen if R is a radical of formula (H 5 C 2 O) 2 P(O)CH 2 NHCO—.    
     
     
         2 . A composition according to  claim 1 , wherein R is a radical of formula  
       
         
           
           
               
               
           
         
         wherein R 33  and R 34  together are  
         
           
             
             
                 
                 
             
           
         
         R 37  and R 38  are each independently of the other C 1 -C 4 alkyl; or R 37  and R 38 , taken together, are —(CH 2 ) 5 —; and R 39  is hydrogen, C 1 -C 4 alkyl or  
         
           
             
             
                 
                 
             
           
         
       
     
     
         3 . A composition according to  claim 1 , wherein R is a radical of formula  
       
         
           
           
               
               
           
         
       
       wherein R 21  is methyl, ethyl, propyl, 2-propenyl or 2-butenyl, and R 22  and R 25  are hydrogen.  
     
     
         4 . A composition according to  claim 3 , wherein R 21  is 2-propenyl.  
     
     
         5 . A composition according to  claim 1 , wherein R is a radical of formula  
       
         
           
           
               
               
           
         
       
       wherein R 1  to R 8  are each independently of one another hydrogen or C 1 -C 4 alkyl.  
     
     
         6 . A composition according to  claim 5 , wherein R 1  to R 7  are hydrogen and R 8  is methyl.  
     
     
         7 . A composition according to  claim 1 , wherein R is a radical of formula  
       
         
           
           
               
               
           
         
       
       wherein R 14  is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy, P is C 1 -C 4 alkyl, C 2 -C 4 alkenyl or C 2 -C 4 alkynyl, X is O or S, n is 1, A is a C 1 -C 8 hydrocarbon radical and R 13  is hydrogen or a C 1 -C 5 hydrocarbon radical.  
     
     
         8 . A composition according to  claim 7 , wherein R 14  is C 1 -C 4 alkoxy, P is C 1 -C 4 alkyl, X is O, A is C 1 -C 4 alkylene and R 13  is C 1 -C 4 alkyl.  
     
     
         9 . A composition according to  claim 8 , wherein R 14  is methoxy, P is methyl, A is methylene and R 13  is isopropyl.  
     
     
         10 . A composition according to  claim 1 , wherein R is a radical of formula  
       
         
           
           
               
               
           
         
       
       wherein R 15  and R 16  are each independently of the other hydroxyl, C 1 -C 4 alkyl or C 1 -C 4 alkoxy, R 17  and R 18  are each independently of the other hydrogen or C 1 -C 4 alkyl, and R 19  is hydrogen or a radical of formula —COOR 07 , wherein R 07  is C 1 -C 4 alkyl, and R 20  is hydrogen or C 1 -C 4 alkyl.  
     
     
         11 . A composition according to  claim 10 , wherein R 16  and R 15  are C 1 -C 4 alkoxy, R 17  and R 18  are hydrogen, R 19  is a radical of formula —COOR 07 , wherein R 07  is C 1 -C 4 alkyl, and R 20  is hydrogen.  
     
     
         12 . A composition according to  claim 11 , wherein R 15  and R 16  are isopropoxy and R 19  is —COOC 2 H 5 .  
     
     
         13 . A composition according to  claim 1 , which contains, as compound of formula II, a compound of formula III  
       
         
           
           
               
               
           
         
       
       or of formula IV  
       
         
           
           
               
               
           
         
       
       or of formula V  
       
         
           
           
               
               
           
         
       
     
     
         14 . A method of selectively controlling weeds and grasses in crops of cultivated plants, which comprises treating said plants, the seeds or the locus thereof, concurrently or separately, with an effective amount of a herbicide of formula I according to  claim 1  and, to antagonise said herbicide, an antidotally effective amount of a compound of formula II according to  claim 1 .  
     
     
         15 . A method according to  claim 14 , which comprises treating crops of cultivated plants or areas intended for cropping with cultivated plants, with 0.001 to 10 kg/ha of a compound of formula I and an amount of 0.005 to 0.5 kg/ha of a compound of formula II.  
     
     
         16 . A method according to  claim 14  of selectively controlling weeds and grasses in crops of maize.