Substituted fluoroalkoxyphenylsulfonylureas

Abstract

The invention relates to substituted fluoroalkoxyphenylsulfonylureas of the general formula (I) in which n, A, R 1 , R 2 , R 3 and R 4 are as defined in the description, to their use as plant treatment agents, in particular as herbicides and fungicides, and to a process and intermediates for their preparation.

1 - 10 . (canceled) 
     
     
         11 . A compound of formula (I) 
       
         
           
           
               
               
           
         
         or a salt thereof, 
         in which 
         n represents 2, 
         A represents nitrogen, 
         R 1  represents hydrogen, represents halogen, or represents optionally halogen- or C 1 -C 4 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino, or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, 
         R 2  represents hydrogen, represents cyano, represents halogen, represents optionally halogen- or C 1 -C 4 -alkoxy-substituted alkyl, alkoxy, alkylthio, alkyl-amino, or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or represents cycloalkyl having 3 to 6 carbon atoms, 
         R 3  represents hydrogen or represents optionally cyano-, halogen-, C 1 -C 4 -alkoxy-, or C 1 -C 4 -alkoxycarbonyl-substituted alkyl having 1 to 4 carbon atoms, and 
         R 4  represents halogen, represents optionally cyano-, halogen-, or C 1 -C 4 -alkoxy-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms, represents optionally cyano- or halogen-substituted alkenyl, alkynyl, alkenyloxy, or alkynyl-oxy having in each case 2 to 4 carbon atoms, or represents optionally cyano-, halogen-, or C 1 -C 4 -alkyl-substituted cycloalkyl having 3 to 6 carbon atoms. 
       
     
     
         12 . A compound according to  claim 11  in which
 n represents 2,   A represents nitrogen,   R 1  represents hydrogen, fluorine, chlorine, or bromine, or represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-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, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-, or t-butylamino, dimethylamino, or diethylamino,   R 2  represents hydrogen, fluorine, cyano, chlorine, or bromine, represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-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, methyl-amino, ethylamino, n- or i-propylamino, n-, i-, s-, or t-butylamino, dimethylamino, or diethylamino, or represents cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,   R 3  represents hydrogen or represents optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, or n- or i-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s-, or t-butyl, and   R 4  represents fluorine, chlorine, or bromine, represents optionally fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s-, or t-butoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, methoxy, ethoxy, n- or i-propoxy, or n-, i-, s-, or t-butoxy, represents optionally fluorine-, chlorine-, and/or bromine-substituted ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy, or butynyloxy, or represents optionally fluorine-, chlorine-, or methyl-substituted cyclopropyl, cyclobutyl, or cyclopentyl.   
     
     
         13 . A compound according to  claim 11  in which
 n represents 2,   A represents nitrogen,   R 1  represents hydrogen, fluorine, chlorine, or bromine, or represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino, or diethylamino,   R 2  represents hydrogen, cyano, fluorine, chlorine, or bromine, represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino, or diethylamino, or represents cyclopropyl,   R 3  represents hydrogen or represents optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methoxycarbonyl-, ethoxycarbonyl-, or n- or i-propoxycarbonyl-substituted methyl, ethyl, or n- or i-propyl, and   R 4  represents fluorine, chlorine, or bromine, represents optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, or n- or i-propoxy, represents optionally fluorine-, chlorine-, and/or bromine-substituted propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy, or butynyloxy, or represents optionally fluorine-, chlorine-, or methyl-substituted cyclopropyl.   
     
     
         14 . A compound according to  claim 11  in which
 n represents 2,   A represents nitrogen,   R 1  represents cyano, chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoro-methoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, or cyclopropyl,   R 2  represents chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methylthio, ethylthio, methylamino, ethylamino, or dimethylamino,   R 3  represents hydrogen or methyl, and   R 4  represents fluorine, chlorine, bromine, methyl, trifluoromethyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, or cyclopropyl.   
     
     
         15 . A compound according to  claim 11  in which A represents nitrogen, n represents 2, and
 (1) R 1  represents methoxy, R 2  represents methyl, R 3  represents hydrogen, and R 4  represents methyl,   (2) R 1  represents methyl, R 2  represents methoxy, R 3  represents hydrogen, and R 4  represents trifluoromethyl,   (3) R 1  represents methyl, R 2  represents methoxy, R 3  represents hydrogen, and R 4  represents trifluoromethyl, as the sodium salt, or   (4) R 1  represents methoxy, R 2  represents methoxy, R 3  represents hydrogen, and R 4  represents trifluoromethyl.   
     
     
         16 . A process for preparing a compound according to  claim 11  comprising
 (a) reacting substituted an aminoazine of formula (II)   
       
         
           
           
               
               
           
         
         
           in which 
           A, R 1 , and R 2  are as defined for formula (I) in  claim 11 , 
           Z represents halogen, alkoxy, or aryloxy, and 
           R 3  is as defined for formula (I) in  claim 11  or represents the group —C(O)—Z, 
         
          with a fluoroalkoxybenzenesulfonamide of formula (III) 
       
       
         
           
           
               
               
           
         
         
           in and R 4  are as defined for formula (I) in  claim 11 , optionally in the presence of one or more reaction auxiliaries and optionally in the presence of one or more diluents, to give a compound of formula (I), and 
         
         (b) optionally, converting the resulting compound of formula (I) into a corresponding salt. 
       
     
     
         17 . A method for controlling unwanted vegetation comprising allowing one or more compounds according to  claim 11  to act on an unwanted plant and/or its habitat. 
     
     
         18 . A method for controlling unwanted microorganisms comprising allowing one or more compounds according to  claim 11  to act on an unwanted microorganism and/or its habitat. 
     
     
         19 . A herbicidal or fungicidal composition comprising a compound according to  claim 11  and customary extenders and/or surfactants. 
     
     
         20 . A compound of formula (III) 
       
         
           
           
               
               
           
         
         in which 
         n represents 2, and 
         R 4  represents halogen, represents optionally cyano-, halogen-, or C 1 -C 4 -alkoxy-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms, represents optionally cyano- or halogen-substituted alkenyl, alkynyl, alkenyloxy, or alkynyl-oxy having in each case 2 to 4 carbon atoms, or represents optionally cyano-, halogen-, or C 1 -C 4 -alkyl-substituted cycloalkyl having 3 to 6 carbon atoms.