title: New α-Methylene-γ-Butyrolactone Derivatives as Potential Fungicidal Agents: Design, Synthesis and Antifungal Activities.
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.
authors.affiliation: Research &amp; Development Center of Biorational Pesticide, Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Northwest A &amp; F University, Xinong Road 22, Yangling 712100, Shaanxi, China. wuyongling39@126.com.
authors.forename: Yongling
authors.initials: Y
authors.lastname: Wu
authors.affiliation: Research &amp; Development Center of Biorational Pesticide, Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Northwest A &amp; F University, Xinong Road 22, Yangling 712100, Shaanxi, China. rizhaoalong@163.com.
authors.forename: Delong
authors.initials: D
authors.lastname: Wang
authors.affiliation: Research &amp; Development Center of Biorational Pesticide, Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Northwest A &amp; F University, Xinong Road 22, Yangling 712100, Shaanxi, China. gaoyanqinggc@nwsuaf.edu.cn.
authors.forename: Yanqing
authors.initials: Y
authors.lastname: Gao
authors.affiliation: Research &amp; Development Center of Biorational Pesticide, Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Northwest A &amp; F University, Xinong Road 22, Yangling 712100, Shaanxi, China. fengjt67@hotmail.com.
authors.forename: Juntao
authors.initials: J
authors.lastname: Feng
authors.affiliation: Research &amp; Development Center of Biorational Pesticide, Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Northwest A &amp; F University, Xinong Road 22, Yangling 712100, Shaanxi, China. zhxing1952@126.com.
authors.forename: Xing
authors.initials: X
authors.lastname: Zhang
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D020171:Botrytis / Q000187:drug effects; D020231:Colletotrichum / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D021281:Quantitative Structure-Activity Relationship
chemical_list: D000935:Antifungal Agents; C014096:alpha-methylene gamma-butyrolactone; D015107:4-Butyrolactone
keywords: antifungal activity; ester and ether derivatives; heuristic method; quantitative structure-activity relationships (QSAR); α-methylene-γ-butyrolactone