Synthesis and Phytocytogenotoxic Activity of N-Phenyl-2-phenoxyacetamides Derived from Thymol.

Abstract

The excessive use of herbicides has caused a series of problems related to human health, environmental pollution, and an increase in the resistance of plants to commercial herbicides. As an alternative, natural compounds and their semisynthetic derivatives have been widely studied to obtain environmentally friendly and more effective herbicides than the usual ones. In view of these factors, the aim of this work was to synthesize new molecules with herbicidal potential using thymol as a starting material, a natural phenol that has a pronounced phytotoxic effect. Novel N-phenyl-2-thymoxyacetamides were synthesized and characterized by MS and by 1H and 13C NMR. All prepared molecules were subjected to phytotoxic and cytotoxic activity assays using Lactuca sativa L. and Sorghum bicolor L. as model plants. Molecules containing chlorine in the para position of the thymoxy group exhibited phytotoxic and cytogenotoxic effects superior to those of the commercial herbicides 2,4-D and glyphosate.