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Herbicidal Activity of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. and Echinochloa crus-galli (L.) Beauv.
[Image: see text] 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 arom...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2019
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6906942/ https://www.ncbi.nlm.nih.gov/pubmed/31858061 http://dx.doi.org/10.1021/acsomega.9b03144 |
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author | Chotsaeng, Nawasit Laosinwattana, Chamroon Charoenying, Patchanee |
author_facet | Chotsaeng, Nawasit Laosinwattana, Chamroon Charoenying, Patchanee |
author_sort | Chotsaeng, Nawasit |
collection | PubMed |
description | [Image: see text] 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. |
format | Online Article Text |
id | pubmed-6906942 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-69069422019-12-19 Herbicidal Activity of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. and Echinochloa crus-galli (L.) Beauv. Chotsaeng, Nawasit Laosinwattana, Chamroon Charoenying, Patchanee ACS Omega [Image: see text] 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. American Chemical Society 2019-11-27 /pmc/articles/PMC6906942/ /pubmed/31858061 http://dx.doi.org/10.1021/acsomega.9b03144 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Chotsaeng, Nawasit Laosinwattana, Chamroon Charoenying, Patchanee Herbicidal Activity of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. and Echinochloa crus-galli (L.) Beauv. |
title | Herbicidal Activity
of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. and Echinochloa
crus-galli (L.)
Beauv. |
title_full | Herbicidal Activity
of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. and Echinochloa
crus-galli (L.)
Beauv. |
title_fullStr | Herbicidal Activity
of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. and Echinochloa
crus-galli (L.)
Beauv. |
title_full_unstemmed | Herbicidal Activity
of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. and Echinochloa
crus-galli (L.)
Beauv. |
title_short | Herbicidal Activity
of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. and Echinochloa
crus-galli (L.)
Beauv. |
title_sort | herbicidal activity
of flavokawains and related trans-chalcones against amaranthus tricolor l. and echinochloa
crus-galli (l.)
beauv. |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6906942/ https://www.ncbi.nlm.nih.gov/pubmed/31858061 http://dx.doi.org/10.1021/acsomega.9b03144 |
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