Abstract:

Anethole-based carboxylic acid, which maintained the phenylpropanoid C6-C3 active structural unit in anethole, was prepared by Perkin condensation reaction of propionic anhydride with anisaldehyde obtained by the oxidation of anethole. Then, nineteen anethole-based diacylhydrazine compounds(6a-6s) were synthesized via esterification, hydrazinolysis, and N-acylation reactions. All the target compounds were characterized by FT-IR, ¹H NMR, ¹³C NMR, and ESI-MS. Their antifungal activity against eight tested plant pathogens was also evaluated. The results showed that, the target compounds showed certain antifungal activity against the eight tested plant pathogens, at the mass concentration of 50 mg/L. Among them, compounds 6a(R=H), 6f(R=m-Cl), 6o(R=p-I), 6p(R=p-OH), and 6q(R=p-t-Bu) had inhibition rates of 94.8%, 96.1%, 91.7%, 96.1%, and 91.7% against Physalospora piricola(all in A-class activity level), which were much better than that of the positive control chlorothalonil. Compounds 6f(R=m-Cl) and 6p(R=p-OH) were worthy of further investigation.

Key words: anethole, anisaldehyde, diacylhydrazine, antifungal activity, synthesis