Location: Natural Products Utilization ResearchTitle: Synthesis and pesticidal activity of new 1,3,4-oxadiazole thioether compounds containing a trifluoro-methylpyrazoyl moiety
|SHI, HAI-BO - Ningbo University|
|ZHAI, ZHI-WHEN - Zhejiang University|
|MIN, LI-JING - Huzhou University|
|HAN, LIANG - Zhejiang University|
|SUN, NA-BO - Zhejiang Shuren University|
|DUKE, STEPHEN - University Of Mississippi|
|LIU, XING-HAI - Zhejiang University|
Submitted to: Research on Chemical Intermediates
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 9/16/2022
Publication Date: 9/20/2022
Citation: Shi, H., Zhai, Z., Min, L., Han, L., Sun, N., Cantrell, C.L., Bajsa Hirschel, J.N., Duke, S.O., Liu, X. 2022. Synthesis and pesticidal activity of new 1,3,4-oxadiazole thioether compounds containing a trifluoro-methylpyrazoyl moiety. Research on Chemical Intermediates. https://doi.org/10.1007/s11164-022-04839-x.
Interpretive Summary: New agricultural fungicides are needed because of evolving resistance. In order to find new fungicides, a series of new 1,3,4-oxadiazole compounds were designed and synthesized by using penthiopyrad as a template compound. Some of synthesized triazole compounds had good fungicidal activity against the plant pathogens Sclerotinia sclerotiorum and Rhizoctonia solani. In silico studies found that the most active compound acts on fungi by inhibition of succinate dehydrogenase.
Technical Abstract: In order to find new lead compounds with high pesticidal activity, a series of 1,3,4-oxadiazole compounds (5 series) were designed and synthesized by using penthiopyrad as a synthon. Their structures were confirmed by 1H NMR and HRMS, and the crystal structure of 2-(benzylthio)-5-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)-1,3,4-oxadiazole (5a) was determined by X-ray single crystal diffraction. Some of the synthesized triazole compounds exhibited good fungicidal activity (>50% inhibition) against the plant pathogens Sclerotinia sclerotiorum and Rhizoctonia solani at 50 µg/mL.