Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters
AbstractTwenty-seven (Z)- and (E)-verbenone derivatives bearing an oxime ester moiety were designed and synthesized in search of novel bioactive molecules. Their structures were confirmed by UV-Vis, FTIR, NMR, ESI-MS, and elemental analysis. The antifungal and herbicidal activities of the target compounds were preliminarily evaluated. As a result, compound (E)-4n (R = β-pyridyl) exhibited excellent antifungal activity with growth inhibition percentages of 92.2%, 80.0% and 76.3% against Alternaria solani, Physalospora piricola, and Cercospora arachidicola at 50 µg/mL, showing comparable or better antifungal activity than the commercial fungicide chlorothalonil with growth inhibition of 96.1%, 75.0% and 73.3%, respectively, and 1.7−5.5-fold more growth inhibition than its stereoisomer (Z)-4n (R = β-pyridyl) with inhibition rates of 22.6%, 28.6% and 43.7%, respectively. In addition, seven compounds displayed significant growth inhibition activity of over 90% against the root of rape (Brassica campestris) at 100 µg/mL, exhibiting much better herbicidal activity than the commercial herbicide flumioxazin with a 63.0% growth inhibition. Among these seven compounds, compound (E)-4n (R = β-pyridyl) inhibited growth by 92.1%, which was 1.7-fold more than its stereoisomer (Z)-4n (R = β-pyridyl) which inhibited growth by 54.0%. View Full-Text
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Hu, Q.; Lin, G.-S.; Duan, W.-G.; Huang, M.; Lei, F.-H. Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters. Molecules 2017, 22, 1678.
Hu Q, Lin G-S, Duan W-G, Huang M, Lei F-H. Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters. Molecules. 2017; 22(10):1678.Chicago/Turabian Style
Hu, Qiong; Lin, Gui-Shan; Duan, Wen-Gui; Huang, Min; Lei, Fu-Hou. 2017. "Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters." Molecules 22, no. 10: 1678.
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