Synthesis, crystal structure, herbicidal activities and 3D-QSAR study of some novel 1,2,4-triazolo[4,3-a]pyridine derivatives

• Published in: Pest management science 2015-02, Vol.71 (2), p.292-301
• Main Authors: Liu, Xing-Hai, Xu, Xiao-Yan, Tan, Cheng-Xia, Weng, Jian-Quan, Xin, Jia-Hua, Chen, Jie
• Format: Article
• Language: English
• Subjects: 1,2,4‐triazolo[4,3‐a]pyridine; 3-a]pyridine; 3D-QSAR; 4-triazolo; Chemical compounds; Crystal structure; Diffraction; herbicidal activities; Herbicides; Herbicides - chemical synthesis; Herbicides - chemistry; Herbicides - pharmacology; Herbicides - toxicity; Magnoliopsida - drug effects; Plant Weeds - drug effects; Pyridines - chemical synthesis; Pyridines - chemistry; Pyridines - pharmacology; Pyridines - toxicity; Quantitative Structure-Activity Relationship; Species Specificity; synthesis; Triazoles - chemical synthesis; Triazoles - chemistry; Triazoles - pharmacology; Triazoles - toxicity; Weeds; X-ray diffraction
• ISSN: 1526-498X; 1526-4998
• DOI: 10.1002/ps.3804

BACKGROUND 1,2,4‐Triazolo[4,3‐a]pyridine derivatives represent a new series of compounds that possess good herbicidal activity against Echinochloa crusgalli (L.) Beauv., Setaria faberii, Digitaria sanguinalis (L.) Scop., Brassica juncea Coss., Amaranthus retroflexus L. and Eclipta prostrata L. RESULTS A total of 23 novel 1,2,4‐triazolo[4,3‐a]pyridine derivatives were synthesised and identified by 1H NMR, IR, single‐crystal X‐ray diffraction, mass‐spectroscopic and elemental analysis, and their herbicidal activities were tested against E. crusgalli (L.) Beauv., S. faberii, D. sanguinalis (L.) Scop., B. juncea Coss., A. retroflexus L. and E. prostrata L. at 150 g a.i. ha−1. It was found that the title compound 8‐chloro‐3‐(4‐propylphenyl)‐[1,2,4]‐triazolo[4,3‐a]pyridine possesses high herbicidal activity and a broad spectrum against the 22 test weeds, with an inhibition effect of about 50% at a dosage of 37.5 g a.i. ha−1, and is safe for corn, cotton and rice at a dosage of 150 g a.i. ha−1. Furthermore, comparative molecular field analysis contour models were established to study the structure–activity relationship of the title compounds. CONCLUSION It is possible that, with further structure modification, 1,2,4‐triazolo[4,3‐a]pyridine derivatives, which possess good herbicidal activities, may become novel lead compounds for the development of herbicides against dicotyledonous weeds. © 2014 Society of Chemical Industry