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ARS Home » Southeast Area » Oxford, Mississippi » Natural Products Utilization Research » Research » Publications at this Location » Publication #394512
Research Project: Biobased Pesticide Discovery and Product Optimization and Enhancement from Medicinal and Aromatic Crops

Location: Natural Products Utilization Research

Title: Synthesis and pesticidal activity of new 1,3,4-oxadiazole thioether compounds containing a trifluoro-methylpyrazoyl moiety

Author
item SHI, HAI-BO - Ningbo University
item ZHAI, ZHI-WHEN - Zhejiang University
item MIN, LI-JING - Huzhou University
item HAN, LIANG - Zhejiang University
item SUN, NA-BO - Zhejiang Shuren University
item Cantrell, Charles
item Bajsa-Hirschel, Joanna
item DUKE, STEPHEN - University Of Mississippi
item 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.
DOI: 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.