Design, Synthesis, and Antifungal Activity of 3‐(Thiophen‐2‐yl)‐1,5‐dihydro‐2H‐pyrrol‐2‐one Derivatives Bearing a Carbonic Ester Group

Abstract

A series of 3‐(thiophen‐2‐yl)‐1,5‐dihydro‐2H‐pyrrol‐2‐one derivatives bearing a carbonic ester group were designed and synthesized by integrating a thiophene nucleus and a pyrroline‐2‐one scaffold in a single molecular architecture. Their structures were confirmed by IR, 1H‐NMR, EI‐MS, and elemental analyses, and their antifungal activities against Fusarium graminearum (Fg), Rhizoctorzia solani (Rs), and Botrytis cinerea (Bc) were evaluated. The antifungal bioassays indicated that some title compounds exhibited desirable antifungal effects against the tested fungi. Strikingly, the title compounds 4i, 4k, 4n, and 4o showed obvious antifungal activities against Rs, with corresponding EC50 values of 35.26, 33.56, 23.90, and 30.48 μg/mL, respectively, which are better than that of hymexazol (37.86 μg/mL). These results indicated that 3‐(thiophen‐2‐yl)‐1,5‐dihydro‐2H‐pyrrol‐2‐one derivatives bearing a carbonic ester group can serve as potential structural templates in the search for novel high‐efficient fungicides.

Design, Synthesis, Antifungal Activity, and 3D-QASR of Novel Oxime Ether-Containing Coumarin Derivatives as Potential Fungicides

“…The antifungal activities of the target compounds were examined at an equivalent concentration of 50 μg/mL using mycelia growth inhibitory rate methods according to the published literature. − Meanwhile, boscalid was tested as the positive control at the same concentration. The in vivo anti- B. cinerea effect of 5a and anti -R. solani effect of 6b were evaluated on tomatoes and rice leaves in fruit and detached leaf assays, where boscalid and validamycin, respectively, served as positive controls.…”