Use of dithiine-tetracarboximides for controlling phytopathogenic fungi

Abstract

The present invention relates to the use of novel and of known dithiine-tetracarboximides for controlling phytopathogenic fungi, and to methods of controlling phytopathogenic fungi in plant protection, and to plant protection compositions comprising these dithiine-tetracarboximides.

1 . Use of dithiine-tetracarboximides of the general formula (I) 
     
       
         
         
             
             
         
       
       in which 
       R 1  and R 2  are identical or different and represent hydrogen, C 1 -C 8 -alkyl which is optionally monosubstituted or polysubstituted by halogen, —OR 3 , —COR 4 , or represent C 3 -C 7 -cycloalkyl which are optionally monosubstituted or polysubstituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, or represent aryl or aryl-(C 1 -C 4 -alkyl), each of which is optionally monosubstituted or polysubstituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, —COR 4  or sulphonylamino, 
       R 3  represents hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, or represents aryl which is optionally monosubstituted or polysubstituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, 
       R 4  represents hydroxyl, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, 
       n represents 0 or 1 
     
     for controlling phytopathogenic fungi. 
   
   
       2 . Use according to  claim 1 , characterized in that
 R 1  and R 2  are identical or different and represent hydrogen, or represent C 1 -C 6 -alkyl which is optionally monosubstituted or polysubstituted by fluorine, chlorine, bromine, —OR 3 , —COR 4 , or represent C 3 -C 7 -cycloalkyl which is optionally monosubstituted or polysubstituted by chlorine, methyl or trifluoromethyl, or represent phenyl or phenyl-(C 1 -C 4 -alkyl), each of which is optionally monosubstituted or polysubstituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, —COR 4 , sulphonylamino,   R 3  represents hydrogen, methyl, ethyl, methylcarbonyl, ethylcarbonyl or represents phenyl which is optionally monosubstituted or polysubstituted by fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl or trifluoromethyl,   R 4  represents hydroxyl, methyl, ethyl, methoxy or ethoxy,   n represents 0 or 1.   
   
   
       3 . Use according to  claim 1 , characterized in that
 R 1  and R 2  are identical or different and represent hydrogen, or represent C 1 -C 4 -alkyl which is optionally monosubstituted or polysubstituted by fluorine, chlorine, hydroxyl, methoxy, ethoxy, methylcarbonyloxy, carboxyl, or represent C 3 -C 7 -cycloalkyl which is optionally monosubstituted or polysubstituted by chlorine, methyl or trifluoromethyl, or represent phenyl, benzyl, 1-phenethyl, 2-phenethyl or 2-methyl-2-phenethyl, each of which is optionally monosubstituted to trisubstituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, —COR 4 , sulphonylamino,   R 3  represents hydrogen, methyl, methylcarbonyl or phenyl,   R 4  represents hydroxyl or methoxy,   n represents 0 or 1.   
   
   
       4 . Use according to  claim 1 , characterized in that R 1  and R 2  simultaneously represent methyl. 
   
   
       5 . Composition for controlling phytopathogenic fungi, characterized in that it contains at least one dithiine-tetracarboximide of the formula (I) according to  claim 1 , besides extenders and/or surface-active substances. 
   
   
       6 . Method of controlling phytopathogenic fungi, characterized in that dithiine-tetracarboximides of the formula (I) according to  claim 1  are applied to the fungi and/or their environment. 
   
   
       7 . Dithiine-tetracarboximides of the formula (I-a) 
     
       
         
         
             
             
         
       
       in which 
       R 1a  and R 2a  are identical or different and represent C 1 -C 8 -alkyl which is monosubstituted or polysubstituted by fluorine, —OR 3a , —COR 4a , or represent C 3 -C 7 -cycloalkyl which is optionally monosubstituted or polysubstituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, or represent aryl-(C 1 -C 4 -alkyl) which is monosubstituted in the alkyl moiety by —COR 4a , 
       R 3a  represents C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, or represents aryl which is optionally monosubstituted or polysubstituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, 
       R 4a  represents hydroxyl, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, 
       r represents 0 or 1, 
     
     where R 1a  and R 2a a do not simultaneously represent acetoxymethyl or methoxymethyl. 
   
   
       8 . Dithiine-tetracarboximides of the formula (I-a) according to  claim 8 , in which
 R 1a  and R 2a  are identical or different and represent C 1 -C 6 -alkyl which is monosubstituted or polysubstituted by fluorine, —OR 3a , —COR 4a , or represent C 3 -C 7 -cycloalky which is optionally monosubstituted or polysubstituted by chlorine, methyl or trifluoromethyl, or represent phenyl-(C 1 -C 4 -alkyl) which is monosubstituted in the alkyl moiety by —COR 4a ,   R 3a  represents methyl, ethyl, methylcarbonyl, ethylcarbonyl, or represents phenyl which is optionally monosubstituted or polysubstituted by fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl or trifluoromethyl,   R 4a  represents hydroxyl, methyl, ethyl, methoxy or ethoxy,   r represents 0 or 1,   
     where R 1a  and R 2a  do not represent acetoxymethyl. 
   
   
       9 . Dithiine-tetracarboximides of the formula (I-a) according to  claim 8  or  9 , in which
 R 1a  and R 2a  are identical or different and represent C 1 -C 4 -alkyl which is monosubstituted or polysubstituted by fluorine, hydroxyl, methoxy, ethoxy, methylcarbonyloxy, carboxyl, or represent C 3 -C 7 -cycloalkyl which is optionally monosubstituted or polysubstituted by chlorine, methyl or trifluoromethyl, or represent 1-phenethyl or 2-phenethyl, each of which is monosubstituted in the alkyl moiety by —COR 4a ,   R 3a  represents methyl, methylcarbonyl or phenyl,   R 4a  represents hydroxyl or methoxy,   r represents 0,   
     where R 1a  and R 2a  a do not represent acetoxymethyl. 
   
   
       10 . Use of dithiine-diisoimides of the formula (V) 
     
       
         
         
             
             
         
       
     
     in which R 1  and R 2  have the meanings given in  claim 1  for controlling phytopathogenic fungi. 
   
   
       11 . Dithiine-diisoimides of the formula (V-a) 
     
       
         
         
             
             
         
       
     
     in which R 1a  and R 2a  have the meanings given in  claim 7 .