Synthesis and herbicidal activity of 1,2,4-triazole derivatives containing a pyrazole moiety

Authors: MU, JIN-XIA - China Jiliang University; ZHAI, ZHI-WEN - Zhejiang University Of Technology; TAN, CHENG-XIA - Zhejiang University Of Technology; WENG, JIAN-QUAN - Zhejiang University Of Technology; WU, HONG-KE - Zhejiang University Of Technology; Duke, Stephen; ZHANG, YONG-GANG - Shandong Academy Of Agricultural Sciences; LIU, XING-HAI - Zhejiang University Of Technology

Submitted to: Journal of Heterocyclic Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 7/12/2018
Publication Date: 1/16/2019
Citation: Mu, J., Zhai, Z., Tan, C., Weng, J., Wu, H., Duke, S.O., Zhang, Y., Liu, X. 2019. Synthesis and herbicidal activity of 1,2,4-triazole derivatives containing a pyrazole moiety. Journal of Heterocyclic Chemistry. http://doi.org/10.1002/jhet.3476.
DOI: https://doi.org/10.1002/jhet.3476

Interpretive Summary: A series of triazole derivatives containing a pyrazole moiety were synthesized and chemically characterized. The herbicidal activities of these compounds were tested against lettuce and bentgrass. Most of the tested compounds were moderately herbicidal against lettuce and bentgrass.

Technical Abstract: N-heterocycles have been of great research interest because of their diverse biological activities. Diazole and triazole derivatives with excellent fungicide activities have been commercialized as pharmaceuticals (miconazole) and agrochemicals (propiconazole), respectively. Synthesis of substituted 1,2,4-triazole compounds is an important field, especially in pharmaceutical and agrochemical discovery efforts. There are numerous reports in the literature on 1,2,4-triazole compounds with various interesting activities, including antifungal, anti-cancer, antibacterial, anti-inflammatory, ketol-acid reductoisomerase inhibitory, antileishmanial, and others. Pyrazole is a five membered diazole heterocycle, which is a key substructure in many drugs and pesticides. For example, many succinate dehydrogenase inhibitor fungicides contain a pyrazole moiety. Chlorantraniliprole an insecticide developed by Dupont company contains a pyrazole ring. Pyrazole derivatives possess diverse biological activites, such as antibacterial, G protein-coupled receptor 52 (GPR52) agonists, nematocidal, anti-mitotic, antidiabetic, antifungal and others. In our previous work, some 1,2,4-triazole compounds were designed and synthesized. They showed good antifungal and herbicidal activities. In this paper, a series of novel 1,2,4-triazole derivatives were designed and synthesized. Their chemical structures were confirmed by 1H NMR and HRMS. The herbicidal activity of these 1,2,4-triazoles were determined on a dicotyledonous and monocotyledonous plant species.