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

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Yongling WuXing Zhang

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 he...Continue Reading

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Citations

Feb 6, 2017·Bioorganic & Medicinal Chemistry Letters·Yong-Ling WuXing Zhang
Jan 11, 2020·Frontiers in Chemistry·Jozef KollárJaroslav Mosnáček
Feb 6, 2020·Biomedicine & Pharmacotherapy = Biomédecine & Pharmacothérapie·Qijuan LiHuiling Hu
Apr 4, 2021·International Journal of Molecular Sciences·Joonseong HurJaehoon Sim

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Methods Mentioned

BETA
column chromatography

Software Mentioned

CODESSA
Gaussian
Ampac
Gaussian 03W
QSAR

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