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 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 () and monocotyledonous barnyard grass (). The inhibition rates of compounds and reached up to 96% and 95% for the root of rape () 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.