Abstract:
Verbenone was prepared by selective oxidation of
α-pinene at first. Then, by oximation of the carbonyl group (
Z)-and(
E)-verbenone oxime compounds were synthesized and separaed, followed by the nucleophilic substitution reaction to afford forty novel (
Z)-and (
E)-verbenone oxime ether compounds
4a-4t, including twenty couples of
Z/E isomers. The structures of the target compounds were characterized by
1H NMR,
13C NMR, FT-IR, UV-vis, and ESI-MS. The antifungal activities of the target compounds were evaluated. The results showed that, at the mass concentration of 50 mg/L, all the target products exhibited certain inhibition activities against the eight kinds of plant pathogens. Compound(
E)-
4r(R=2, 6-Cl) had inhibition rates of 77.8% against
Physalospora piricola. Compound(
E)-
4s(R=2, 6-F) had inhibition rates of 72.7% against
Rhizoctonia solani. Compound (
E)-
4n(R=
p-CN) had inhibition rates of 70.8% against
Helmithosporium maydis. Certain difference were found in inhibition activity of
Z-E isomers against some plant pathogens. The CoMFA model(
r2=0.992,
q2=0.507) of (
E)-verbenone oxime ether compounds for inhibiting
Rhizoctonia solani was established for the study of 3D-QSAR, and the results could provide a basis for the design of potential lead compounds with higher activity.