AUTHOR=Wang Xing , Luo Mu-Jia , Wang Yu-Xuan , Han Wen-Qing , Miu Jian-Xin , Luo Xi-Ping , Zhang Ai-Dong , Kuang Yi 

TITLE=Design, synthesis, and herbicidal activity of indole-3-carboxylic acid derivatives as potential transport inhibitor response 1 antagonists

JOURNAL=Frontiers in Chemistry

VOLUME=Volume 10 - 2022

YEAR=2022

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2022.975267

DOI=10.3389/fchem.2022.975267

ISSN=2296-2646

ABSTRACT=Auxins as an important class of phytohormones play essential roles in a plant’s life cycle, therefore, developing compounds with auxin-like properties for plant growth regulation and weed control applications is of great significance. Herein, we report 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. cruss-galli). The inhibition rates of compounds 10d and 10h reach up to 96% and 95% for the root of rape (B. napus) at 100 mg/L, and they also maintain 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.