Study of the Interference in Target Seed Germination Caused by Dienamides and Epoxy Derivatives, in the Search for New Herbicides

Abstract

The indiscriminate use of herbicides makes weeds resistant, increasing the demand for more efficient herbicides. Novel potential herbicides were prepared from sorbic acid, being 8 dienamides and 6 epoxides. Subsequently, phytotoxic activities of sorbic acid and 14 synthesized compounds were evaluated against sorghum, onion, cucumber, lettuce, and beggartick seeds. Furthermore, the protein target of the most active substance in plants was identified in silico. Among the tested compounds, (2E,4E)-N-(p-fluorophenyl)hexa-2,4-dienamide (2c), (2E,4E)-N-(o-naphthyl) hexa-2,4-dienamide (2d), (E)-N-methylphenyl-3-((2R,3R)-3-methyloxiran-2-yl)acrylamide (3b), (E)-N-bromophenyl-3-((2R,3R)-3-methyloxiran-2-yl)acrylamide (3e), and (E)-N-methoxyphenyl3-((2R,3R)-3-methyloxiran-2-yl)acrylamide (3f) showed pronounced inhibitory activities, both of shoots and roots, making them candidates for promising herbicides. All compounds altered seed development, and compounds 2c, 2d, 3b, 3e, and 3f presented equal or superior results to the commercial control herbicide S-metolachlor. Docking studies suggest that enzyme mitogenactivated protein kinase can be the target of those compounds.

N‐Phenylnorbornenesuccinimide derivatives, agricultural defensive, and enzymatic target selection

“…Epoxides represent another class of compounds with potential biological activity, and our research group has conducted investigations into the development of agrochemicals containing this functional group 14–17 . In one of our most recent studies, Ramos and collaborators synthesized and assessed the herbicidal activity of epoxides derived from (2 E ,4 E )‐hexa‐2,4‐dienoic acid, yielding favorable results 18 …”