Inspired
by the application of natural products against pathogenic
fungi, two series of dehydroabietyl oxime ester derivatives were synthesized
using rosin as a raw material. Based on the evaluation and screening
of in vitro antifungal activities against Botrytis cinerea (B. cinerea), Sclerotinia sclerotiorum, Valsa mali, Rhizoctonia solani, Fusarium oxysporum, and Alternaria alternata, compound 4f exhibited
the best antifungal activity against B. cinerea, and its EC50 was 0.798 mg/L, which was lower than that
of the positive control trifloxystrobin (1.112 mg/L). The in vivo antifungal activity results showed that 4f had satisfactory protective and curative effects on tomato. Physiological
and biochemical studies showed that the action mechanism of compound 4f against B. cinerea is to
change the morphology and the ultrastructure of the mycelium, increase
the permeability of the cell membrane, and cause nucleus and mitochondrial
dysfunction, thus leading to apoptosis. In addition, qualitative and
quantitative structure–activity relationship studies showed
that the inductive and conjugative interactions between compound 4f and the target receptor form an electron transfer process,
thereby achieving an antifungal effect. These results indicated that
compound 4f, which was derived from the natural product
rosin, is a novel potential fungicidal candidate against B. cinerea.