{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,5]],"date-time":"2026-06-05T23:14:35Z","timestamp":1780701275662,"version":"3.54.1"},"reference-count":30,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2017,10,12]],"date-time":"2017-10-12T00:00:00Z","timestamp":1507766400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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 = \u03b2-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 \u00b5g\/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\u22125.5-fold more growth inhibition than its stereoisomer (Z)-4n (R = \u03b2-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 \u00b5g\/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 = \u03b2-pyridyl) inhibited growth by 92.1%, which was 1.7-fold more than its stereoisomer (Z)-4n (R = \u03b2-pyridyl) which inhibited growth by 54.0%.<\/jats:p>","DOI":"10.3390\/molecules22101678","type":"journal-article","created":{"date-parts":[[2017,10,12]],"date-time":"2017-10-12T13:06:19Z","timestamp":1507813579000},"page":"1678","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":30,"title":["Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters"],"prefix":"10.3390","volume":"22","author":[{"given":"Qiong","family":"Hu","sequence":"first","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, Guangxi, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gui-Shan","family":"Lin","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, Guangxi, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wen-Gui","family":"Duan","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, Guangxi, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Min","family":"Huang","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, Guangxi, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fu-Hou","family":"Lei","sequence":"additional","affiliation":[{"name":"Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008, Guangxi, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2017,10,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"597","DOI":"10.1016\/S0008-6215(02)00529-3","article-title":"Characterization of an acetylated heteroxylan from Eucalyptus globulus Labill","volume":"338","author":"Evtuguin","year":"2003","journal-title":"Carbohydr. 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