Benzofuran-2-acetic esters as a new class of natural-like herbicides.

In recent decades, the use of synthetic herbicides has been increasing, mainly in emerging countries. However, their intensive and indiscriminate application is a major cause of environmental pollution and human health injury. Therefore, there is an increasing need to develop new herbicides with safer toxicological and environmental profiles. A promising strategy is to synthesize new molecules containing the core of natural products as a template for the production of 'bio-inspired' or 'natural-like' herbicides.The potential herbicidal activity of some benzofuran-2-acetic esters was assessed in vitro on Arabidopsis thaliana, a model species. All five molecules (M1-M5) showed significant phytotoxic activity, reducing both shoot and root system at low concentrations. In particular, methyl 2-(5-methoxybenzofuran-2-yl)hexanoate (M3) exhibited the highest phytotoxicity displayed against two crops and weeds, monocots (Zea mays L. and E. crus-galli) and dicots (Lactuca sativa L. and Amaranthus retroflexus L.). The M3 activity was also compared with glyphosate, a common herbicide, showing a lower but similar activity. Moreover, the results evidenced that M3 was more effective in post-emergency.Readily synthesizable benzofuran-2-acetic esters possessing the benzofuran ring as 'bio-inspired' core, show significant herbicidal activity making them very efficient even at low concentrations. They can be sprayed in liquid form, and the addition of adjuvants can improve penetration through the leaf cuticle. These results confirm the importance of these molecules as models for the development of new natural-like herbicides. © 2019 Society of Chemical Industry.