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.
Highlights
Plant pathogenic fungi remain a main cause of plant diseases, which can infect any tissue of a plant and cause severe yield agricultural product losses [1,2,3]
Synthesis γ-hydroxy-α-methylene esters, which were obtained under mild aqueous reaction conditions through
Structures the derivatives were characterized by 1H-Nuclear magnetic resonance (NMR), relationships, different acids wereThe reacted with of theallthree kinds of intermediate compounds to obtain
Summary
Plant pathogenic fungi remain a main cause of plant diseases, which can infect any tissue of a plant and cause severe yield agricultural product losses [1,2,3]. Colletotrichum lagenarium and Botrytis cinerea are the most common plant pathogenic fungi, and can cause cross-infections between diseased and healthy plants [5,6,7]. They cause significant reductions of crop yield and quality [8]. Traditional chemical fungicides play an important role in killing or controlling target fungi directly, but sometimes cause adverse effects to the environment and food, and often create fungicide resistance [9]. It is urgent to develop novel and effective fungicidal agents to protect plants
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