Amino-1,3,5-triazines N-substituted with chiral bicyclic radicals, process for their preparation, compositions thereof, and their use as herbicides and plant growth regulators

Abstract

The invention related to an optically active compound of formula (I) or a salt thereof: wherein the various symbols are as defined in the description, to processes for their preparation, to compositions thereof, and to their use as herbicides or plant growth regulators. The invention also relates to novel intermediates of formula (III), (V) and (XIII) as defined in the description.

1 . A compound of the formula (V), or salts thereof, 
       
         
           
           
               
               
           
         
       
       wherein
 R 6  is H, (C 1 -C 6 )alkyl or (C 1 -C 6 )alkoxy; 
 R 7 , R 8 , R 9  and R 10  are each independently H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl, halogen, (C 1 -C 3 )alkoxy, (C 1 -C 3 )haloalkoxy or CN; 
 A is CH 2 , O or a direct bond; and wherein the stereochemical configuration at the marked 1 position is (R) having a stereochemical purity of from 60 to 100% (R), with the exception of compounds of formula (V), or salts thereof, where: 
 (i) A is a direct bond, R 6 , R 7 , R 8  and R 9  are each hydrogen, and R 10  is hydrogen, methoxy, n-propoxy or cyano; or
 A is a direct bond, R 6 , R 7 , R 8  and R 10  are each hydrogen, and R 9  is fluoro; 
 A is a direct bond, R 6 , R 9  and R 10  are each hydrogen, and R 7  is methoxy and R 8  are methoxy; 
 
 (ii) A is CH 2 , and R 6 , R 7 , R 8  and R 10  are each hydrogen, and R 9  is hydrogen, methyl, methoxy, isopropoxy, n-propyl or t-butyl; or
 A is CH 2 , and R 6 , R 7  and R 9  are each hydrogen, and R 8  is methyl and R 10  is methyl; or 
 A is CH 2 , and R 6 , R 8  and R 10  are each hydrogen, and R 7  is methyl and R 9  is methyl; 
 A is CH 2 , and R 6 , R 7 , R 9  and R 10  are each hydrogen, and R 8  is methoxy; or 
 A is CH 2 , and R 6 , R 8 , R 9  and R 10  are each hydrogen, and R 7  is methoxy; or 
 
 (iii) A is an oxygen atom, and R 6 , R 7 , R 8 , R 9  and R 10  are each H. 
 
     
     
         2 . The compound of  claim 1  which is a compound of the formula (Va) or salts thereof: 
       
         
           
           
               
               
           
         
       
       wherein:
 R 6  is methyl; 
 R 7  and R 10  are each independently H or methyl; 
 R 8  is H, methyl, Cl or F; 
 R 9  is H, methyl, Cl, F or Br; and 
 A is a direct bond, CH 2  or O 
 and the stereochemical configuration at the marked 1 position is (R) having a stereochemical purity of from 60 to 100% (R), 
 and the stereochemical configuration at the marked 2 position is (S) having a stereochemical purity of from 60 to 100% (S). 
 
     
     
         3 . The compound of  claim 1  which is a compound of the formula (Vb) or salts thereof: 
       
         
           
           
               
               
           
         
       
       wherein:
 R 6  is methyl; 
 R 7  and R 10  are each independently H or methyl; 
 R 8  is H, methyl, Cl or F; 
 R 9  is H, methyl, Cl, F or Br; and 
 A is a direct bond, CH 2  or O 
 and the stereochemical configuration at the marked 1 position is (R) having a stereochemical purity of from 60 to 100% (R), 
 and the stereochemical configuration at the marked 2 position is (R) having a stereochemical purity of from 60 to 100% (R). 
 
     
     
         4 . A compound of formula (XIII) or a salt thereof, 
       
         
           
           
               
               
           
         
       
       in which
 R 6  is H, (C 1 -C 6 )alkyl or (C 1 -C 6 )alkoxy; and R 7 , R 8 , R 9  and R 10  are each independently H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl, halogen, (C 1 -C 3 )alkoxy, (C 1 -C 3 )haloalkoxy or CN; 
 R 11  is (C 1 -C 6 )alkanoyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )alkoxy and (C 1 -C 4 )alkylthio; 
 A is CH 2 , O or a direct bond; and wherein the stereochemical configuration at the marked 1 position is (R) having a stereochemical purity of from 60 to 100% (R), 
 with the exception of compounds of formula (XIII), or salts thereof, where: 
 (i) A is a direct bond, R 6 , R 7 , R 8 , R 9  and R 10  are each hydrogen, and R 11  is formyl, acetyl, propionyl, n-butanoyl, n-hexanoyl, trifluoroacetyl or bromacetyl; or
 A is a direct bond, R 6  is methyl; R 7 , R 8 , R 9  and R 10  are each hydrogen, and R 11  is acetyl, or 
 A is a direct bond, R 6 ; R 7 , R 9  and R 10  are each hydrogen, R 8  is fluoro, and R 11  is acetyl, or 
 A is a direct bond, R 6 ; R 7 , R 8  and R 10  are each hydrogen, R 9  is fluoro, and R 11  is acetyl, or 
 A is a direct bond, R 6 ; R 9  and R 10  are each hydrogen, R 7  is methoxy, and R 8  is methoxy, or 
 
 (ii) A is CH 2 , and R 6 , R 7 , R 8 , R 9  and R 10  are each hydrogen, and R 11  is acetyl, trifluoroacetyl, chloroacetyl or butanoyl; or
 A is CH 2 , and R 6 , R 7  and R 9  are each hydrogen, and R 8  is methyl and R 10  is methyl; and R 11  is acetyl, or 
 A is CH 2 , and R 6 , R 7 , R 9  and R 10  are each hydrogen, and R 8  is methoxy, and R 11  is acetyl, or 
 A is CH 2 , and R 6  is methyl, R 7 , R 8 , R 9  and R 10  are each hydrogen, and R 11  is acetyl, or 
 A is CH 2 , and R 6 , R 8 , R 9 , and R 10  are each hydrogen, R 7  is methoxy, and R 11  is bromoacetyl or chloropropionyl; or 
 A is CH 2 , and R 6 , R 8  and R 10  are each hydrogen, and R 7  is methyl and R 9  is methyl; and R 11  is acetyl, or 
 A is CH 2 , and R 7 , R 8 , R 9  and R 10  are each hydrogen, R 6  is methyl, and R 11  is acetyl; or 
 
 (iii) A is an oxygen atom, and R 6 , R 7 , R 8 , R 9  and R 10  are each H, and R 11  is acetyl. 
 
     
     
         5 . The compound of  claim 4  which is a compound of formula (XIII) or a salt thereof, 
       
         
           
           
               
               
           
         
       
       wherein:
 R 6  is methyl; 
 R 7  and R 10  are each independently H or methyl; 
 R 8  is H, methyl, Cl or F; 
 R 9  is H, methyl, Cl, F or Br; and 
 R 11  is (C 1 -C 6 )alkanoyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )alkoxy and (C 1 -C 4 )alkylthio; 
 A is a direct bond, CH 2  or O 
 and the stereochemical configuration at the marked 1 position is (R) having a stereochemical purity of from 60 to 100% (R), 
 and the stereochemical configuration at the marked 2 position is (S) having a stereochemical purity of from 60 to 100% (S). 
 
     
     
         6 . A compound of formula (III) or a salt thereof, 
       
         
           
           
               
               
           
         
       
       wherein
 R 4  and R 5  are each independently H, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 3 -C 4 )alkenyl, (C 3 -C 4 )haloalkenyl, (C 3 -C 4 )alkynyl, (C 3 -C 4 )haloalkynyl or an acyl radical; 
 R 6  is H, (C 1 -C 6 )alkyl or (C 1 -C 6 )alkoxy; 
 R 7 , R 8 , R 9  and R 10  are each independently H, (C 1 -C 4 )alkyl, (C 1 -C 3 )haloalkyl, halogen, (C 1 -C 3 )alkoxy, (C 1 -C 3 )haloalkoxy or CN; 
 A is CH 2 , O or a direct bond; 
 and the stereochemical configuration at the marked 1 position is (R) having a stereochemical purity of from 60 to 100% (R). 
 
     
     
         7 . A compound of formula (III) or a salt thereof as claimed in claim  16 , wherein
 R 6  is (C 1 -C 6 )alkyl,   and the stereochemical configuration at the marked 2 position is (S) having a stereochemical purity of from 60 to 100% (S).