Fungicidal 5-phenyl substituted 2-(cyanoamino) pyrimidines

Abstract

Pyrimidines of formula I in which R 1 represents hydrogen or alkyl, haloalkyl, alkenyl, alkynyl, alkadienyl, alkoxy, cycloalkyl, phenyl, or 5- or 6-membered heteroaryl or 5- or 6-membered heterocyclyl, containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom, or tri-alkyl-silyl, formyl or alkoxycarbonyl,  wherein R 1 groups are unsubstituted or substituted as defined in the specification; R 2 represents phenyl, cycloalkyl or 5- or 6-membered heteroaryl, containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom, which are unsubstituted or substituted; R 3 represents hydrogen, halogen or alkyl, alkoxy, alkylthio, alkylamino or dialkylamino; which are unsubstituted or substituted; R 4 represents hydrogen or alkyl, alkenyl or alkynyl; which are unsubstituted or substituted; and X represents O, S, NR 5 or a single bond, wherein R 5 represents hydrogen or alkyl; or  R 1 and R 5 together with the interjacent nitrogen atom form a heterocyclic ring; processes and intermediates for preparing these compounds, to compositions comprising them and to their use for controlling harmful fungi.

1 - 10 . (canceled)  
   
   
       11 . 2-Thiopyrimidine derivatives of the formulae XIII, XIV, or IX:  
     
       
         
         
             
             
         
       
     
     wherein 
 R 2  represents phenyl, C 3 -C 6 -cycloalkyl or 5- to 6-membered heteroaryl, containing one to for nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom, which are unsubstituted or substituted by one to three groups R a ;  
 R a  is halogen, nitro, cyano, hydroxyl or C 1 -C 10 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 10 -haloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 10 -alkoxy, C 1 -C 10 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, tri-C 1 -C 4 -alkylsilyl, phenyl, halo- or dihalophenyl or 5- to 6-membered heteroaryl, containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom;  
 R 3  represents hydrogen, hydroxyl, halogen or C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy, C 1 -C 10 -alkylthio, C 1 -C 10 -alkylamino or di-C 1 -C 10 -alkylamino, which are unsubstituted or substituted by one to three groups R a ;  
 R 6  is C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl, and  
 Hal is a halogen atom.  
 
   
   
       12 . 2-Thiopyrimidine derivatives as claimed in  claim 11 , wherein R 2  is phenyl which is substituted by 1, 2 or 3 groups R a .  
   
   
       13 . 2-Thiopyrimidine derivatives as claimed in  claim 12 , wherein R 2  is phenyl which is substituted by 2 or 3 groups R a .  
   
   
       14 . 2-Thiopyrimidine derivatives as claimed in  claim 12 , wherein R 2  is a phenyl group of the formula  
     
       
         
         
             
             
         
       
     
     wherein 
 L 1  through L 4  each independently represent hydrogen, fluorine, chlorine or methoxy.  
 
   
   
       15 . 2-Thiopyrimidine derivatives as claimed in  claim 14 , wherein 
 L 1  is fluorine or chlorine;    L 2  and L 4  each independently are hydrogen, fluorine or chlorine; and    L 3  is hydrogen, fluorine, chlorine or methoxy.    
   
   
       16 . 2-Thiopyrimidine derivatives as claimed in  claim 11 , wherein R 6  is methyl.  
   
   
       17 . 2-Thiopyrimidine derivatives as claimed in  claim 11 , wherein R 3  is chlorine.  
   
   
       18 . 2-Thiopyrimidine derivatives as claimed in  claim 11 , wherein R 3  is fluorine.  
   
   
       19 . 2-Thiopyrimidine derivatives as claimed in  claim 11 , wherein R 3  is methyl.