Design, synthesis, and herbicidal activity of novel quaternary ammonium salt derivatives

• Published in: Pesticide biochemistry and physiology Vol. 143; pp. 246 - 251
• Main Authors: Wu, Qiao, Liu, Changling, Yang, Jichun, Guan, Aiying, Ma, Hongjuan
• Format: Journal Article
• Language: English
• Published: United States Elsevier Inc 01.11.2017
• Subjects: Herbicidal activity; Intermediate derivatization methods; Quaternary ammonium salt; Synthesis; Quaternary ammonium salt; Intermediate derivatization methods; Herbicidal activity; Synthesis
• ISSN: 0048-3575; 1095-9939
• DOI: 10.1016/j.pestbp.2017.05.006

A series of novel quaternary ammonium salt derivatives were designed and synthesized by introducing the herbicide carboxylic acid into substituted aminoacetanilide compounds which derived from herbicides alachlor or acetochlor, using the intermediate derivatization methods in an attempt to obtain novel candidates for weed control. The herbicidal activity assays in greenhouse demonstrated that some of the title compounds exhibited good herbicidal activities against velvet leaf, youth-and-old age, barnyard grass, and foxtail. Especially, III9 gave the best activity (EC50 (ga.i/ha): YOA 34.1, VEL 33.6, FOX 15.9, BYG 36.2). The field trials indicated that III9 had better herbicidal activity than the commercial herbicide imazethapyr to control broadleaf weeds at 150ga.i/ha. The present work demonstrated that the quaternary ammonium salt derivatives can be used as potential lead compounds for discovering novel herbicides with improved activity. III9 itself is worthy of being further developed as an herbicidal candidate. Further syntheses, structure optimization studies, and field trials around III9 are in progress. [Display omitted] •Application of the strategies of intermediate derivatization method (IDM)•Detailed structure and activity relationship of target compounds•The structure of quaternary ammonium salts with carboxylate anion plays an important role on herbicidal activity.•Excellent herbicidal activity against velvet leaf, youth-and-old age, barnyard grass, and foxtail in the greenhouse•Compound III9 was almost 2 times higher activity to control broadleaf weeds than imazethapyr at the same dose in the field trials.