Microbicidal active substances

Abstract

The use of oxathiazolones of formula is described, R 1 is C 1 -C 16 alkyl, C 2 -C 16 alkenyl or C 5 -C 8 cycloalkyl, each unsubstituted or substituted by halogen, —CN, —NO 2 , —C═O, —C═S, —NR 2 , —OR 3 , —SR 4 , —SO 2 R 5 , —COOR 6 or by a 1,3,4-oxathiazol-2-one radical; C 6 -C 10 aryl unsubstituted or substituted by one or more C 1 -C 5 alkyl, C 6 -C 10 aryl, halogen, hydroxy, acyl, —CN, —CF 3 , —NO 2 , —NR 2 , —OR 3 , —SR 4 , —SO 3 H, —SO 2 R 5 , —COOR 6 substituents or by a 1,3,4-oxathiazol-2-one radical; or a 5- or 6-membered heterocyclic radical; R 2 and R 3 are each independently of the other hydrogen; C 1 -C 5 alkyl; C 6 -C 10 aryl, or acyl; R 4 is hydrogen; C 1 -C 5 alkyl; or C 6 -C 10 aryl; R 5 is C 1 -C 5 alkyl; or C 6 -C 10 aryl; R 6 is hydrogen; C 1 -C 5 alkyl; or C 6 -C 10 aryl, in the antimicrobial treatment of surfaces. The compounds exhibit a pronounced action against pathogenic gram-positive and gram-negative bacteria, and also against yeasts and moulds.

What is claimed is:  
     
         1 . Use of a compound of formula  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1  is C 1 -C 16 alkyl, C 2 -C 16 alkenyl or C 5 -C 8 cycloalkyl, each unsubstituted or substituted by halogen, —CN, —NO 2 , —C═O, —C═S, —NR 2 , —OR 3 , —SR 4 , —SO 2 R 5 , —COOR 6  or by a 1,3,4-oxathiazol-2-one radical; C 6 -C 10 aryl unsubstituted or substituted by one or more C 1 -C 5 alkyl, C 6 -C 10 aryl, halogen, hydroxy, acyl, —CN, —CF 3 , —NO 2 , —NR 2 , —OR 3 , —SR 4 , —SO 3 H, —SO 2 R 5 , —COOR 6  substituents or by a 1,3,4-oxathiazol-2-one radical; or a 5- or 6-membered heterocyclic radical;  
 R 2  and R 3  are each independently of the other hydrogen; C 1 -C 5 alkyl; C 6 -C 10 aryl, or acyl;  
 R 4  is hydrogen; C 1 -C 5 alkyl; or C 6 -C 10 aryl;  
 R 5  is C 1 -C 5 alkyl; or C 6 -C 10 aryl;  
 R 6  is hydrogen; C 1 -C 5 alkyl; or C 6 -C 10 aryl,  
 in the antimicrobial treatment of surfaces.  
 
     
     
         2 . Use according to  claim 1 , wherein in the compound of formula (1) 
 R 1  is C 1 -C 16 alkyl unsubstituted or substituted by halogen, —CN, —NO 2 , —C═O, —C═S, —NR 2 , —OR 3 , —SR 4 , —SO 2 R 5 , —COOR 6  or by a 1,3,4-oxathiazol-2-one radical; or phenyl unsubstituted or substituted by one or more C 1 -C 5 alkyl, hydroxy, halogen substituents or by a 1,3,4-oxathiazol-2-one radical; and    R 2 , R 3 , R 4 , R 5  and R 6  are as defined in  claim 1 .    
     
     
         3 . Use according to  claim 1  or  2 , wherein 
 R 1  is C 1 -C 16 alkyl.  
 
     
     
         4 . Use according to  claim 1  or  2 , wherein there is used an oxathiazolone of formula  
       
         
           
           
               
               
           
         
       
       wherein 
 R 7 , R 8  and R 9  are each independently of the others hydrogen; halogen; hydroxy; or C 1 -C 5 alkyl.  
 
     
     
         5 . Use of a compound of formula (1) in the disinfection of the skin, mucosa and hair.  
     
     
         6 . Use of a compound of formula (1) in the treatment of textile fibre materials.  
     
     
         7 . Use of a compound of formula (1) in washing and cleaning formulations.  
     
     
         8 . Use of a compound of formula (1) in imparting antimicrobial properties to plastics, paper, nonwovens, wood or leather.  
     
     
         9 . A personal care preparation, comprising 
 from 0.01 to 15% by weight, based on the total weight of the composition, of a compound of formula (1), and cosmetically tolerable adjuvants.    
     
     
         10 . An oral composition, comprising 
 from 0.01 to 15% by weight, based on the total weight of the composition, of a compound of formula (1), and orally tolerable adjuvants.    
     
     
         11 . A method of antimicrobial treatment of a surface which comprises contacting said surface with an antimicrobially effective amount of a compound of formula  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1  is C 1 -C 16 alkyl, C 2 -C 16 alkenyl or C 5 -C 8 cycloalkyl, each unsubstituted or substituted by halogen, —CN, —NO 2 , —C═O, —C═S, —NR 2 , —OR 3 , —SR 4 , —SO 2 R 5 , —COOR 6  or by a 1,3,4-oxathiazol-2-one radical;  
 R 2  and R 3  are each independently of the other hydrogen; C 1 -C 5 alkyl; C 6 -C 10 aryl, or acyl;  
 R 4  is hydrogen; C 1 -C 5 alkyl; or C 6 -C 10 aryl;  
 R 5  is C 1 -C 5 alkyl; or C 6 -C 10 aryl; and  
 R 6  is hydrogen; C 1 -C 5 alkyl; or C 6 -C 10 aryl.  
 
     
     
         12 . A method according to  claim 11 , wherein in the compound of formula (1) 
 R 1  is C 1 -C 16 alkyl unsubstituted or substituted by halogen, —CN, —NO 2 , —C═O, —C═S, —NR 2 , —OR 3 , —SR 4 , —SO 2 R 5 , —COOR 6  or by a 1,3,4-oxathiazol-2-one radical; and    R 2 , R 3 , R 4 , R 5  and R 6  are as defined in  claim 11 .    
     
     
         13 . A method according to  claim 11 , wherein R 1  is C 1 -C 16 alkyl.  
     
     
         14 . A method according to  claim 11 , which comprises contacting skin, mucosa or hair with a compound of formula (1).  
     
     
         15 . A method according to  claim 11 , which comprises contacting textile fibre materials with a compound of formula (1).  
     
     
         16 . A method according to  claim 11  in which a compound of formula (1) is used in a washing and/or cleaning formulation.  
     
     
         17 . A method of imparting antimicrobial properties to plastics, paper, nonwovens, wood or leather, which comprises contacting said materials with an antimicrobially effective amount of a compound of formula (1) according to  claim 11 .  
     
     
         18 . A personal care preparation, comprising 
 from 0.01 to 15% by weight, based on the total weight of the composition, of a compound of formula                           wherein    R 1  is C 1 -C 16 alkyl, C 2 -C 16 alkenyl or C 5 -C 8 cycloalkyl, each unsubstituted or substituted by halogen, —CN, —NO 2 , —C═O, —C═S, —NR 2 , —OR 3 , —SR 4 , —SO 2 R 5 , —COOR 6  or by a 1,3,4-oxathiazol-2-one radical;    R 2  and R 3  are each independently of the other hydrogen; C 1 -C 5 alkyl; C 6 -C 10 aryl, or acyl;    R 4  is hydrogen; C 1 -C 5 alkyl; or C 6 -C 10 aryl;    R 5  is C 1 -C 5 alkyl; or C 6 -C 10 aryl; and    R 6  is hydrogen; C 1 -C 5 alkyl; or C 6 -C 10 aryl,    and a cosmetically tolerable adjuvant.    
     
     
         19 . An oral composition, comprising 
 from 0.01 to 15% by weight, based on the total weight of the composition, of a compound of formula                           wherein    R 1  is C 1 -C 16 alkyl, C 2 -C 16 alkenyl or C 5 -C 8 cycloalkyl, each unsubstituted or substituted by halogen, —CN, —NO 2 , —C═O, —C═S, —NR 2 , —OR 3 , —SR 4 , —SO 2 R 5 , —COOR 6  or by a 1,3,4-oxathiazol-2-one radical;    R 2  and R 3  are each independently of the other hydrogen; C 1 -C 5 alkyl; C 6 -C 10 aryl, or acyl;    R 4  is hydrogen; C 1 -C 5 alkyl; or C 6 -C 10 aryl;    R 5  is C 1 -C 5 alkyl; or C 6 -C 10 aryl; and    R 6  is hydrogen; C 1 -C 5 alkyl; or C 6 -C 10 aryl,    and an orally tolerable adjuvant.