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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...

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Autores principales: Wang, Xing, Luo, Mu-Jia, Wang, Yu-Xuan, Han, Wen-Qing, Miu, Jian-Xin, Luo, Xi-Ping, Zhang, Ai-Dong, Kuang, Yi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
Materias:
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.
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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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