Substituted triazines and a method for producing same

Abstract

The present invention provides aromatic 4,6-bis-trichloromethyl-s-triazin-2-yl compounds of formula (I), a process for producing para-disubstituted benzonitriles as precursor to give compounds of formula (I) and a process for the production thereof.

1 .- 7 . (canceled) 
     
     
         8 . Compounds of formula (I) 
       
         
           
           
               
               
           
         
         wherein X is halogen and R 1 , R 2 , R 3  and R 4  are each independently hydrogen, halogen, alkyl, alkoxy, alkenyl, alkynyl, alkylthio, alkylseleno, wherein R 1  and R 2  and/or R 3  and R 4  may combine to form a 3 to 5-membered saturated or unsaturated bridge optionally substituted with up to 2 heteroatoms and R 5  is linear C 5  to C 20  alkyl which is optionally substituted in any manner by halogen and/or C 1  to C 10  alkyl and/or C 1  to C 10  alkoxy and in which up to six carbon atoms may be replaced by oxygen, in which case at least two carbon atoms shall be present between two oxygen atoms and the R 5  moiety starts with at least two carbon atoms, wherein the terminal methyl group of the linear C 5  to C 20  alkyl moiety shall be unsubstituted. 
       
     
     
         9 . Compounds according to  claim 8 , wherein R 5  may in one embodiment of the invention be linear C 6  to C 20  alkyl which is optionally substituted in any manner by halogen and/or C 1  to C 4  alkyl and/or C 1  to C 4  alkoxy and in which up to six carbon atoms may be replaced by oxygen, in which case at least two carbon atoms shall be present between two oxygen atoms and the R 5  moiety starts with at least two carbon atoms, wherein the terminal methyl group of the linear C 6  to C 20  alkyl moiety shall be unsubstituted. 
     
     
         10 . Compounds according to  claim 8 , wherein X is chlorine and R 1 , R 2 , R 3  and R 4  are each H. 
     
     
         11 . Process for producing the compounds of formula (I) 
       
         
           
           
               
               
           
         
       
       wherein X is halogen and R 1 , R 2 , R 3  and R 4  are each independently hydrogen, halogen, alkyl, alkoxy, alkenyl, alkynyl, alkylthio, alkylseleno, wherein R 1  and R 2  and/or R 3  and R 4  may combine to form a 3 to 5-membered saturated or unsaturated bridge optionally substituted with up to 2 heteroatoms and R 5  is linear C 5  to C 20  alkyl which is optionally substituted in any manner by halogen and/or C 1  to C 10  alkyl and/or C 1  to C 10  alkoxy and in which up to six carbon atoms may be replaced by oxygen, in which case at least two carbon atoms shall be present between two oxygen atoms and the R 5  moiety starts with at least two carbon atoms, wherein the terminal methyl group of the linear C 5  to C 20  alkyl moiety shall be unsubstituted by using the process according to  claim 8  which comprises utilizing the one-pot process to prepare para-disubstituted benzonitriles of formula (IV) in a first step and reacting the resulting para-disubstituted benzonitrile with trihaloacetonitrile in a second step.