Design, Synthesis, and Herbicidal Activity of Novel Dihydrochalcones Derived from Flavokawains and Their Analogs

Weeds are a major cause of crop production losses worldwide, and environmentally friendly chemical control based on natural or semisynthetic compounds has attracted increasing attention. In this study, flavokawains, a class of natural chalcones, and their analogues were converted into dihydrochalcones (1–27) via Pd-catalyzed hydrogenation. The herbicidal activities of these compounds were evaluated against Chinese amaranth (Amaranthus tricolor) and barnyard grass (Echinochloa crus-galli). Several compounds significantly inhibited seed germination and seedling growth in both species. Herbicidal activity was strongly influenced by the type and position of aromatic substituents, with electron-withdrawing groups and meta substitution providing higher activity. The meta-chloro derivative (15) exhibited the highest activity, markedly inhibiting seed germination as well as shoot and root growth. Further investigation of its mode of action revealed that this compound interfered with seed imbibition, inhibited α-amylase activity, and affected membrane integrity and malondialdehyde (MDA) levels in A. tricolor in a concentration-dependent manner. These findings provide valuable insights for the development of natural product-derived herbicides.