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. 2019 Nov 27;4(24):20748-20755.
doi: 10.1021/acsomega.9b03144. eCollection 2019 Dec 10.

Herbicidal Activity of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. and Echinochloa crus-galli (L.) Beauv

Nawasit Chotsaeng  1 , Chamroon Laosinwattana  1 , Patchanee Charoenying  1
Affiliations

Herbicidal Activity of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. and Echinochloa crus-galli (L.) Beauv

Nawasit Chotsaeng et al. ACS Omega. .

Abstract

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.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Chemical structures of xanthoxyline, chalcones, and trans-chalcone.
Figure 2
Figure 2
Inhibitory effects of 3 flavokawains and 18 related chalcones on seed germination (A) and shoot (B) and root (C) growth of Chinese amaranth. Aqueous solutions of Tween 80 and butachlor were used as negative and positive references, respectively. Different letters in each graph indicate significant differences (p < 0.05) between treatments. Error bars represent the standard error of an average of four replicates.
Figure 3
Figure 3
Inhibitory effects of 24 synthetic chalcones on seed germination (A) and shoot (B) and root (C) growth of Chinese amaranth. Aqueous solutions of Tween 80 and butachlor were used as negative and positive controls, respectively. Different letters in each graph indicate significant differences (p < 0.05) between treatments. Vertical bars represent the standard error of an average of four replicates.
Figure 4
Figure 4
Inhibitory effects of 3 flavokawains and 42 synthetic chalcones on seed germination and shoot and root growth of barnyardgrass. Aqueous solutions of Tween 80 and butachlor were used as negative and positive controls, respectively. Different letters in each graph indicate significant differences (p < 0.05) between treatments. Horizontal bars represent the standard error of an average of four replicates.
Figure 5
Figure 5
Inhibitory effects of chalcone 14f on seed germination, shoot, and root growths of (A) barnyardgrass and (B) Chinese amaranth. Aqueous solutions of Tween 80 were used as negative control.
Figure 6
Figure 6
Structures of chalcone herbicides discussed here.
See this image and copyright information in PMC

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