Flavokawains have a broad spectrum of biological activities;
however,
the herbicidal activity of these naturally occurring chalcones has
been less investigated. Flavokawains and their analogues were prepared by the Claisen–Schmidt
condensation reaction between xanthoxyline (or aromatic ketones) and
a variety of aromatic and heteroaromatic aldehydes. These compounds
were then evaluated for their inhibitory effect against representative
dicot and monocot plants. Among 45 synthetic chalcones, derivatives
containing phenoxyacetic acid, 4-(N,N-dimethylamino)phenyl, N-methylpyrrole, or thiophenyl
groups inhibited the germination and growth of Chinese amaranth (Amaranthus tricolor L.) with moderate to high degrees
compared to commercial butachlor. For barnyardgrass (Echinochloa crus-galli (L.) Beauv.), most of the
thiophenyl chalcones interrupted shoot and root emergence. This finding
highlighted the importance of functional groups on the herbicidal
activity of chalcones. The level of inhibition also depended on the
applied concentrations, plant species, and plant organs. (E)-2-(2-(3-Oxo-3-(thiophen-2-yl)prop-1-enyl)phenoxy)acetic
acid (14f) was the most active compound among 45 derivatives.
This chalcone could be a promising structure for controlling the germination
and growth of weeds. The structure–activity relationship results
provide useful information about the development of active chalconoids
as novel natural product-like herbicides.