First synthesis, rotamerism and herbicidal evaluation of substituted s-triazines with amino-1,3-dioxane groups

Abstract

First pure enantiomeric 5-amino-1,3-dioxane, obtained by total diastereospecific ring closure of (1S,2S)-2-amino-1-(4-ni-trophenyl)-1,3- propanediol ("nitrophenylserinol") reacted with cyanuryl chloride to afford N-substituted amino-s-triazines and melamine. Their rotameric behaviour around the Csp2(s-triazine)-N(1,3-dioxane) bond is discussed in terms of NMR, as steric and electronic influence of the substituents. The herbicidal evaluation of one of the new compounds is also described.