Sulphonylbenzazolones

Abstract

Sulphonylbenzazolones of the formula in which R 1 , R 2 , R 3 , R 4 , R 5 and Q are each as defined in the description. a process for preparing these compounds and their use as microbicides in crop protection and in the protection of materials.

1 . Sulphonylbenzazolones of the formula  
       
         
           
           
               
               
           
         
       
       in which 
 R 1 , R 2 , R 3  and R 4  independently of one another each represent hydrogen, halogen, cyano, nitro, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, optionally substituted cycloalkyl, hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyl-carbonyl, cycloalkoxycarbonyl, represent  
                     R 6  represents optionally substituted aryl or represents optionally substituted heterocyclyl,    Z represents a direct bond, represents —CH 2 —, O, S, SO 2  or CO or 
 represents —CO—O— where the oxygen atom is linked to R 6 , or  
 represents —SO2—O— where the sulphur atom is linked to R 6 , or  
 represents —S—CH 2 —SO 2 — where the sulpur atom of the thio group is linked to R 6 , or  
 represents —NH—SO 2 — where the sulphonyl group is linked to R 6 ,  
   R 7  and R 8  independently of one another represent hydrogen, alkyl, halogenoalk1, alkoxyalkyl, alkylcarbonyl, optionally substituted aryl, optionally substituted arylcarbonyt, optionally substituted arylsulphonyl, optionally substituted arylaminocarbonyl or optionally substituted arylmethylsulphonyl or    R 7  and R 8  together with the nitrogen atom to which they are attached represent an optionally alkyl-substituted heterocyclic ring which may contain an additional oxygen atom or an alkylimino group and    W represents a direct bond, a sulphonyl group or a carbonyl group, or    
 R 1  and R 2 , or R 2  and R 3 , or R 3  and R 4  together each represent an optionally substituted alkylene chain having 3 or 4 members in which one or two (non-adjacent) carbon atoms may be replaced by oxygen atoms,  
 R 5  represents optionally substituted unsaturated heterocyclyl and  
 Q represents oxygen or sulphur.  
 
     
     
         2 . Sulphonylbenzazolones of the formula (I) as claimed in  claim 1  in which 
 R 1 , R 2 , R 3  and R 4  independently of one another each represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, straight-chain or branched alkyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, straight-chain or branched alkoxy having 1 to 8 carbon atoms, straight-chain or branched halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, straight-chain or branched alkylthio having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, straight-chain or branched alkylsulphinyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylsulphinyl having 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, straight-chain or branched alkylsulphonyl having 1 to 8 carbon atoms, straight-chain or branched halogenoalkylsulphonyl having 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to 6 carbon atoms which is optionally mono- to pentasubstituted by identical or different halogens and/or alkyls having 1 to 4 carbon atoms, represents hydroxycarbonyl, alkylcarbonyl having 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, alkoxycarbonyl having 1 to 6 carbon atoms in the straight-chain or branched alkoxy moiety, cycloalkylcarbonyl having 3 to 6 carbon atoms in the cycloalkyl moiety, cyclo-alkoxycarbonyl having 3 to 6 carbon atoms in the cycloalkyl moiety, represents 
 —Z—R 6  or  
                     
  in which  
 R 6  represents aryl having 6 to 10 carbon atoms, each of these radicals being mono- to trisubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylsulphinyl having 1 to 4 carbon atoms, alkylsulphonyl having 1 to 4 carbon atoms, halogenoalkylsulphinyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms and/or halogenoalkylsulphonyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms,  
 or  
 R 6  represents an unsaturated heterocyclyl radical having 5 or 6 ring members and 1 to 3 heteroatoms such as nitrogen, oxygen and/or sulphur, it being possible for these radicals to be mono- to tristbstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkoxycarbonyl having 1 to 3 carbon atoms in the alkoxy moiety, cycloalkyl having 3 to 6 carbon atoms, cyano and/or nitro,  
 Z represents a direct bond, and also represents —CH 2 —, O, S, SO 2  or CO or 
 represents —CO—O— where the oxygen atom is linked to R 6 , or  
 represents —SO 2 —O— where the sulphur atom is linked to R 6 , or  
 represents —S—CH 2 —SO 2 — where the sulphur atom of the thio group is linked to R 6 , or  
 represents —NH—SO 2 — where the sulphonyl group is linked to R 6 ,  
 
 R 7  and R 8  independently of one another each represent hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to S identical or different halogen atoms, straight-chain or branched alkoxyalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, alkylcarbonyl having 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, aryl having 6 to 10 carbon atoms, arylcarbonyl having 6 to 10 carbon atoms in the aryl moiety, arylsulphonyl having 6 to 10 carbon atoms, arylaminocarbonyl hating 6 to 10 carbon atoms in the aryl moiety or represents urylmethylsulphonyl having 6 to 10 carbon atoms in the aryl moiety, it being possible for each of the abovementioned aryl radicals to be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, hatogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylsulphinyl having 1 to 4 carbon atoms, alkylsulphonyl having 1 to 4 carbon atoms, halogenoalkylsulphinyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms and/or halogenoalkylsulphonyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms,  
 or  
 R 7  and R 8  together with the nitrogen atom to which they are attached additionally also represent a heterocyclic ring having 5 or 6 ring members which may contain an additional oxygen atom or a C 1 -C 4 -alkylimino group and which is optionally mono- to trisubstituted by alkyl having 1 to 4 carbon atoms,  
 and  
 W represents a direct bond, a sulphonyl group or a carbonyl group,  
 
 and  
 R 1  and R 2 , or R 2  and R 3 , or R 3  and R 4  together each represent an alkylene chain having 3 or 4 members in which one or two (non-adjacent) carbon atoms may be replaced by oxygen atoms and which is optionally mono- to hexasubstituted by halogen, alkyl having 1 to 4 carbon atoms and/or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, 
 R 5  represents an unsaturated heterocyclyl radical having 5 or 6 ring members and 1 to 3 heteroatoms such as oxygen, nitrogen and/or sulphur, it being possible for these radicals to be optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, alkylsulphonyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylsulphonyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each of the two alkyl chains, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety, alkylcarbonyloxy having 1 to 4 carbon atoms in the alkyl moiety, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, alkylsulphonytoxy having 1 to 4 carbon atoms, hydroximinoalkyl having 1 to 4 carbon atoms, alkoximinoalkyl having 1 to 4 carbon atoms in each of the two alkyl chains, halogenoalkoxycarbonyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms in the halogenoatkoxy moiety and/or cycloalkyl having 3 to 6 carbon atoms,  
 and  
 
 Q represents oxygen or sulphur.  
 
     
     
         3 . Process for preparing sulphonylbenzazolones of the formula (I) according to  claim 1 , characterized in that benzazolones of the formula  
       
         
           
           
               
               
           
         
       
       in which 
 R 1 , R 2 , R 3 , R 4  and Q are each as defined above  
 are reacted with a sulphonyl halide of the formula  
 R 5 -SO 2 -X  (III)  
 in which  
 R 5  is as defined above and  
 X represents halogen,  
 if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.  
 
     
     
         4 . Microbicidal compositions, characterized by a content of at least one sulphonylbenzazolone of the formula (1) according to  claim 1 .  
     
     
         5 . Use of sulphonylbenzazolones of the formula (1) according to  claim 1  as microbicides in crop protection and in the protection of materials.  
     
     
         6 . Method for controlling undesirable microorganisms in crop protection and in the protection of materials, characterized in that sulphonylbenzazolones of the formula (I) according to  claim 1  are applied to the microorganisms and/or their habitat.  
     
     
         7 . Process for preparing microbicidal compositions, characterized in that sulphonylbenzazolones of the formula (1) according to  claim 1  are mixed with extenders and/or surface-active agents.  
     
     
         8 . Sulphonylbenzazolone according to  claim 1 , characterized by the formula  
       
         
           
           
               
               
           
         
       
     
     
         9 . Sulphonylbenzazolone according to  claim 1 , characterized by the formula  
       
         
           
           
               
               
           
         
       
     
     
         10 . Sulphonylbenzazolone according to  claim 1 , characterized by the formula