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Molecules 2017, 22(10), 1678; doi:10.3390/molecules22101678

Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters

1
School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, Guangxi, China
2
Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008, Guangxi, China
*
Authors to whom correspondence should be addressed.
Received: 13 September 2017 / Accepted: 7 October 2017 / Published: 12 October 2017
(This article belongs to the Section Organic Synthesis)
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Abstract

Twenty-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
Keywords: α-pinene; verbenone; oxime; (Z)- and (E)-isomer; antifungal activity; herbicidal activity α-pinene; verbenone; oxime; (Z)- and (E)-isomer; antifungal activity; herbicidal activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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.

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