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Molecules 2016, 21(2), 130; doi:10.3390/molecules21020130

New α-Methylene-γ-Butyrolactone Derivatives as Potential Fungicidal Agents: Design, Synthesis and Antifungal Activities

Research & Development Center of Biorational Pesticide, Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Northwest A & F University, Xinong Road 22, Yangling 712100, Shaanxi, China
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Author to whom correspondence should be addressed.
Academic Editor: Thomas J. Schmidt
Received: 10 December 2015 / Revised: 18 January 2016 / Accepted: 19 January 2016 / Published: 22 January 2016
(This article belongs to the Section Medicinal Chemistry)
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Abstract

In consideration of the fact that the α-methylene-γ-butyrolactone moiety is a major bio-functional group in the structure of carabrone and possesses some agricultural biological activity, forty-six new ester and six new ether derivatives containing α-methylene-γ-butyrolactone moieties were synthesized, and their fungicidal activities against Colletotrichum lagenarium and Botrytis cinerea were investigated. Most of the synthesized compounds showed moderate to significant fungicidal activity. Among them, halogen atom-containing derivatives showed better activity than others, especially compounds 6a,d which exhibited excellent fungicidal activity against C. lagenarium, with IC50 values of 7.68 and 8.17 μM. The structure-activity relationship (SAR) analysis indicated that ester derivatives with electron-withdrawing groups on the benzene ring showed better fungicidal activity than those with electron-donating groups. A quantitative structure-activity relationship (QSAR) model (R2 = 0.9824, F = 203.01, S2 = 0.0083) was obtained through the heuristic method. The built model revealed a strong correlation of fungicidal activity against C. lagenarium with the molecular structures of these compounds. These results are expected to prove helpful in the design and exploration of low toxicity and high efficiency α-methylene-γ-butyrolactone-based fungicides. View Full-Text
Keywords: α-methylene-γ-butyrolactone; ester and ether derivatives; antifungal activity; quantitative structure-activity relationships (QSAR); heuristic method α-methylene-γ-butyrolactone; ester and ether derivatives; antifungal activity; quantitative structure-activity relationships (QSAR); heuristic method
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Wu, Y.; Wang, D.; Gao, Y.; Feng, J.; Zhang, X. New α-Methylene-γ-Butyrolactone Derivatives as Potential Fungicidal Agents: Design, Synthesis and Antifungal Activities. Molecules 2016, 21, 130.

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