Potential of 2-Hydroxyacetophenone Derivatives and Simple Phenol's for the control of Meloidogyne javanica

Abstract

Objective: In this study, a series of synthetic hydroxylated (5-10) and prenylated (10-17) acetophenones, chalcones (18-20) and a flavone (21) have been synthesized and evaluated on the nematode Meloidogyne javanica. Additional phenolic compounds, including salicylic acid, isopropyl salicylate, thymol, carvacrol, cumic acid, eugenol, vanillin, and vanillic acid (22-29), were also tested. Methods: Compounds 5-21 have been synthesized by a sequence of reactions and were isolated and identified by 1H-NMR, 13C-NMR, and HRMS. The in vitro nematicidal effects of the compounds were tested on J2 juveniles. The nematicidal activity was confirmed by their egg hatching inhibition effects, tested at the minimum lethal concentration (minimum dose to give 100% J2 mortality). Results: Compounds 5-18 have been previously reported and 19-21 are described here for the first time. The 2´-hydroxylated acetophenones (5-9) showed strong nematicidal effects, being 7-9 the most active. Salicylic (22) and cumic (26) acids were effective compounds. Compounds 7, 12, 22-26, active on M. javanica J2 juveniles, were also egg hatching inhibitors. Conclusions: A C-2/C-4 dihydroxylation or C-2/C-4/C-3 trihydroxylation of the acetophenone moiety improved the activity, while introducing a hydrophilic isoprene chain (10-17) eliminated the effect, with only one prenylated acetophenone (12) being active. Among the additional phenolic compounds (22-29), these with a carboxyl group instead of the acyl side were better nematicides. These results generate molecular leads for developing new nematicidal phenolic compounds.