In the present study, we isolated linalool, geraniol, carvacrol, thymol, menthol and eugenol; synthesised their phenoxyacetic acid derivatives; and assessed their phytotoxic and genotoxic potentials against weeds and agricultural crops. Moreover, the fungicidal activity of both categories of compounds against 12 fungi was examined. Finally, using probabilistic assessment based on Risk Quotient (RQ) by the Monte Carlo simulation (MCS) method, we examined human health risks via oral exposure to these compounds. Toxic potencies to plants demonstrated that all parameters and related indices including germination percentage, mean germination time, germination rate, root length, shoot length, seedling length and vigour index dose-dependently decreased in both weeds and agricultural crops. Based on the comet assay, DNA damage was observed in the root meristems of the plants. Consequently, a significant decrease was observed in head DNA, whereas a significant increase in tail DNA was observed in response to treatments. Besides, the natural components and semisynthetic molecules showed a broad spectrum of fungicidal traits. However, eugenol and eugenoxyacetic acid inhibitory effects on the growth of the tested fungi were similar to that of benomyl. Our probabilistic health risk assessment indicated di minimis risk for natural compo- nents and their phenoxyacetic acid derivatives. Sensitivity analysisshowed that concentrations of residues of the compounds had the most significant effect on risk. Current findings could offer a platform for developing sustainable approaches to reduce chemical residues and their consequent risks to the environment and human health.

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