Biocide polymers, 14. Modification of polyvinyl alcohol with biologically active N‐phosphorylated 3‐amino‐1,2,4‐triazoles

Abstract

Abstract N‐Phosphorylated 3‐amino‐1,2,4‐triazoles, prepared from the herbicide amitrole by acylation with phenyl‐ and 4‐nitrophenyl phosphorodichloridate, respectively, as well as with phosphoryl chloride were reversibly linked to poly(vinyl alcohol) designed for controlled release of the active agent. 4‐N,N′‐Dimethylaminopyridine was used as catalyst for the polymeranalogous esterification reactions. IR, 1 H‐NMR, and 31 P‐NMR analyses of polymers suggest attachment of the herbicide moiety as pendant groups bound via phosphate groups at the ring nitrogen. Comparative hydrolysis studies demonstrated the influence of the substitution degree of PVAL and of the modification of the phosphorus‐to‐triazolide linkage upon the hydrolytic release of amitrole.