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 the numbers 2, 3, or 4,  
 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 alkynyloxy 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 the numbers 2, 3, or 4,    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, methylamino, 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 the numbers 2, 3, or 4,    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 the number 2 or 3,    A represents nitrogen,    R 1  represents cyano, chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoro-methoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoro-ethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, or cyclopropyl,    R 2  represents chlorine, methyl, trifluoromethyl, ethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, methyl-thio, 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 and 
 (1) n represents 2, R 1  represents methoxy, R 2  represents methyl, R 3  represents hydrogen, and R 4  represents methyl,    (2) n represents 2, R 1  represents methyl, R 2  represents methoxy, R 3  represents hydrogen, and R 4  represents trifluoromethyl,    (3) n represents 2, R 1  represents methyl, R 2  represents methoxy, R 3  represents hydrogen, and R 4  represents trifluoromethyl, as the sodium salt,    (4) n represents 3, R 1  represents methyl, R 2  represents methoxy, R 3  represents hydrogen, and R 4  represents n-propyl,    (5) n represents 3, R 1  represents methoxy, R 2  represents methoxy, R 3  represents hydrogen, and R 4  represents n-propyl,    (6) n represents 3, R 1  represents methoxy, R 2  represents methoxy, R 3  represents hydrogen, and R 4  represents methyl,    (7) n represents 2, R 1  represents methoxy, R 2  represents methoxy, R 3  represents hydrogen, and R 4  represents trifluoromethyl, or    (8) n represents 3, R 1  represents methyl, R 2  represents methoxy, R 3  represents hydrogen, and R 4  represents bromine.    
     
     
         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 which n 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 the numbers 2, 3, or 4, 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 alkynyloxy 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.