Triazole derivatives, intermediates thereof and their use as fungicides

Abstract

The present invention relates to novel triazole derivatives, to processes for preparing these compounds, to compositions comprising these compounds, and to the use thereof as biologically active compounds, especially for control of harmful microorganisms in crop protection and in the protection of materials and as plant growth regulators.

1 . A compound of formula (V) 
       
         
           
           
               
               
           
         
         wherein 
         R 1  represents hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, phenyl, phenyl-C 1 -C 4 -alkyl, phenyl-C 2 -C 4 -alkenyl or phenyl-C 2 -C 4 -alkynyl;
 wherein the aliphatic moieties, excluding cycloalkyl moieties, of R 1  may carry 1, 2, 3 or up to the maximum possible number of identical or different groups R a  which independently of one another are selected from 
 R a  halogen, CN, nitro, phenyl, C 1 -C 4 -alkoxy and C 1 -C 4 -halogenalkoxy; wherein the phenyl may be substituted by 1, 2, 3, 4 or 5 substituents selected independently of one another from halogen; CN; nitro; C 1 -C 4 -alkyl; C 1 -C 4 -alkoxy; C 1 -C 4 -halogenalkyl; C 1 -C 4 -halogenalkoxy; 
 wherein the cycloalkyl and/or phenyl moieties of R 1  may carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R b  which independently of one another are selected from 
 R b  halogen, CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl and C 1 -C 4 -halogenalkoxy; 
 
         R 4  represents halogen, CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkoxy, C 1 -C 4 -alkylcarbonyl, hydroxy-substituted C 1 -C 4 -alkyl or pentafluoro-λ 6 -sulfanyl; 
         with the proviso, that R 4  is not represented by CF 3  when R 1  is represented by methyl; 
         m is an integer and is 0, 1, 2, 3, 4 or 5; 
         Y represents a substituted or non-substituted 6-membered aromatic heterocycle selected from 
       
       
         
           
           
               
               
           
         
         
           wherein Y is connected to the O of formula (V) via the bonds identified with “u” and Y is connected to the C(O)(R 1 ) moiety of formula (V) via the bonds identified with “v” and 
           wherein 
           R represents Cl or CF 3 ; 
           R 3  represents halogen, CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -halogenalkoxy; 
           n is an integer and is 0, 1 or 2; 
         
         and/or a salt or N-oxide thereof. 
       
     
     
         2 . A compound of formula (VII) 
       
         
           
           
               
               
           
         
         wherein 
         R 4  represents halogen, CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkoxy, C 1 -C 4 -alkylcarbonyl, hydroxy-substituted C 1 -C 4 -alkyl or pentafluoro-λ 6 -sulfanyl; 
         m is an integer and is 0, 1, 2, 3, 4 or 5; 
         Y represents a substituted or non-substituted 6-membered aromatic heterocycle selected from 
       
       
         
           
           
               
               
           
         
         
           wherein Y is connected to the O of formula (VII) via the bonds identified with “u” and Y is connected to the C(O) moiety of formula (VII) via the bonds identified with “v” and 
           wherein 
           R represents hydrogen, C 1 -C 2 -halogenalkyl, C 1 -C 2 -halogenalkoxy, C 1 -C 2 -alkylcarbonyl or halogen; 
           R 3  represents halogen, CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -halogenalkoxy; 
           n is an integer and is 0, 1 or 2; 
         
         and/or a salt or N-oxide thereof. 
       
     
     
         3 . A compound of formula (IX) 
       
         
           
           
               
               
           
         
         wherein 
         R 1  represents hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, phenyl, phenyl-C 1 -C 4 -alkyl, phenyl-C 2 -C 4 -alkenyl or phenyl-C 2 -C 4 -alkynyl;
 wherein the aliphatic moieties, excluding cycloalkyl moieties, of R 1  may carry 1, 2, 3 or up to the maximum possible number of identical or different groups R a  which independently of one another are selected from 
 R a  halogen, CN, nitro, phenyl, C 1 -C 4 -alkoxy and C 1 -C 4 -halogenalkoxy;
 wherein the phenyl may be substituted by 1, 2, 3, 4 or 5 substituents selected independently of one another from halogen; CN; nitro; C 1 -C 4 -alkyl; C 1 -C 4 -alkoxy; C 1 -C 4 -halogenalkyl; C 1 -C 4 -halogenalkoxy; 
 
 wherein the cycloalkyl and/or phenyl moieties of R 1  may carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R b  which independently of one another are selected from 
 R b  halogen, CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl and C 1 -C 4 -halogenalkoxy; 
 
         R 4  represents halogen, CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy C 1 -C 4 -halogenalkoxy, C 1 -C 4 -alkylcarbonyl, hydroxy-substituted C 1 -C 4 -alkyl or pentafluoro-λ 6 -sulfanyl; 
         m is an integer and is 0, 1, 2, 3, 4 or 5; 
         Y represents a substituted or non-substituted 6-membered aromatic heterocycle selected from 
       
       
         
           
           
               
               
           
         
         
           wherein Y is connected to the O of formula (IX) via the bonds identified with “u” and Y is connected to the oxirane moiety of formula (IX) via the bonds identified with “v” and 
           wherein 
           R represents hydrogen, C 1 -C 2 -halogenalkyl, C 1 -C 2 -halogenalkoxy, C 1 -C 2 -alkylcarbonyl or halogen; 
           R 3  represents halogen, CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -halogenalkoxy; 
           n is an integer and is 0, 1 or 2; 
         
         and/or a salt or N-oxide thereof. 
       
     
     
         4 . The compound of formula (V) according to  claim 1 , wherein
 R 4  represents halogen.   
     
     
         5 . The compound of formula (V) according to  claim 1 , wherein
 m is an integer and is 1 or 2.   
     
     
         6 . The compound of formula (V) according to  claim 1 , wherein
 Y represents   
       
         
           
           
               
               
           
         
         and 
         R represents Cl or CF 3 . 
       
     
     
         7 . The compound of formula (VII) according to  claim 2 , wherein
 R4 represents halogen.   
     
     
         8 . The compound of formula (VII) according to  claim 2 , wherein
 m is an integer and is 1 or 2.   
     
     
         9 . The compound of formula (VII) according to  claim 2 , wherein
 Y represents   and   R represents Cl or CF3.   
     
     
         10 . The compound of formula (IX) according to  claim 3 , wherein
 R4 represents halogen.   
     
     
         11 . The compound of formula (IX) according to  claim 3 , wherein
 m is an integer and is 1 or 2.   
     
     
         12 . The compound of formula (formula (IX) according to  claim 3 , wherein
 Y represents   and   R represents Cl or CF3.