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Design, synthesis, and herbicidal activity of indole-3-carboxylic acid derivatives as potential transport inhibitor response 1 antagonists
Auxins as an important class of phytohormones play essential roles in plant life cycle; therefore, developing compounds with auxin-like properties for plant growth regulation and weed control applications is of great significance. Herein, we reported the design, synthesis, and herbicidal activity ev...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Frontiers Media S.A.
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9360422/ https://www.ncbi.nlm.nih.gov/pubmed/35958241 http://dx.doi.org/10.3389/fchem.2022.975267 |
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author | Wang, Xing Luo, Mu-Jia Wang, Yu-Xuan Han, Wen-Qing Miu, Jian-Xin Luo, Xi-Ping Zhang, Ai-Dong Kuang, Yi |
author_facet | Wang, Xing Luo, Mu-Jia Wang, Yu-Xuan Han, Wen-Qing Miu, Jian-Xin Luo, Xi-Ping Zhang, Ai-Dong Kuang, Yi |
author_sort | Wang, Xing |
collection | PubMed |
description | Auxins as an important class of phytohormones play essential roles in plant life cycle; therefore, developing compounds with auxin-like properties for plant growth regulation and weed control applications is of great significance. Herein, we reported the design, synthesis, and herbicidal activity evaluation of a series of novel indole-3-carboxylic acid derivatives as auxin receptor protein TIR1 antagonists. Petri dish herbicidal activity assay demonstrated that most of the as-synthesized target compounds exhibited good-to-excellent inhibition effects (60–97% inhibitory rates) on roots and shoots of both dicotyledonous rape (B. napus) and monocotyledonous barnyard grass (E. crus-galli). The inhibition rates of compounds 10d and 10h reached up to 96% and 95% for the root of rape (B. napus) at 100 mg/L, and they also maintained 92% and 93% inhibition rates even if at 10 mg/L, respectively. Molecular docking revealed that the interactions between these synthesized target compounds and TIR1 protein include tight π–π stacking, hydrogen bond, and hydrophobic interactions. This work expands the range of auxin chemistry for the development of new auxin mimic herbicides. |
format | Online Article Text |
id | pubmed-9360422 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-93604222022-08-10 Design, synthesis, and herbicidal activity of indole-3-carboxylic acid derivatives as potential transport inhibitor response 1 antagonists Wang, Xing Luo, Mu-Jia Wang, Yu-Xuan Han, Wen-Qing Miu, Jian-Xin Luo, Xi-Ping Zhang, Ai-Dong Kuang, Yi Front Chem Chemistry Auxins as an important class of phytohormones play essential roles in plant life cycle; therefore, developing compounds with auxin-like properties for plant growth regulation and weed control applications is of great significance. Herein, we reported the design, synthesis, and herbicidal activity evaluation of a series of novel indole-3-carboxylic acid derivatives as auxin receptor protein TIR1 antagonists. Petri dish herbicidal activity assay demonstrated that most of the as-synthesized target compounds exhibited good-to-excellent inhibition effects (60–97% inhibitory rates) on roots and shoots of both dicotyledonous rape (B. napus) and monocotyledonous barnyard grass (E. crus-galli). The inhibition rates of compounds 10d and 10h reached up to 96% and 95% for the root of rape (B. napus) at 100 mg/L, and they also maintained 92% and 93% inhibition rates even if at 10 mg/L, respectively. Molecular docking revealed that the interactions between these synthesized target compounds and TIR1 protein include tight π–π stacking, hydrogen bond, and hydrophobic interactions. This work expands the range of auxin chemistry for the development of new auxin mimic herbicides. Frontiers Media S.A. 2022-07-26 /pmc/articles/PMC9360422/ /pubmed/35958241 http://dx.doi.org/10.3389/fchem.2022.975267 Text en Copyright © 2022 Wang, Luo, Wang, Han, Miu, Luo, Zhang and Kuang. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Chemistry Wang, Xing Luo, Mu-Jia Wang, Yu-Xuan Han, Wen-Qing Miu, Jian-Xin Luo, Xi-Ping Zhang, Ai-Dong Kuang, Yi Design, synthesis, and herbicidal activity of indole-3-carboxylic acid derivatives as potential transport inhibitor response 1 antagonists |
title | Design, synthesis, and herbicidal activity of indole-3-carboxylic acid derivatives as potential transport inhibitor response 1 antagonists |
title_full | Design, synthesis, and herbicidal activity of indole-3-carboxylic acid derivatives as potential transport inhibitor response 1 antagonists |
title_fullStr | Design, synthesis, and herbicidal activity of indole-3-carboxylic acid derivatives as potential transport inhibitor response 1 antagonists |
title_full_unstemmed | Design, synthesis, and herbicidal activity of indole-3-carboxylic acid derivatives as potential transport inhibitor response 1 antagonists |
title_short | Design, synthesis, and herbicidal activity of indole-3-carboxylic acid derivatives as potential transport inhibitor response 1 antagonists |
title_sort | design, synthesis, and herbicidal activity of indole-3-carboxylic acid derivatives as potential transport inhibitor response 1 antagonists |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9360422/ https://www.ncbi.nlm.nih.gov/pubmed/35958241 http://dx.doi.org/10.3389/fchem.2022.975267 |
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