Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters
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 w...
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| Format: | Article |
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MDPI AG
2017-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/22/10/1678 |
| _version_ | 1818541906024464384 |
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| author | Qiong Hu Gui-Shan Lin Wen-Gui Duan Min Huang Fu-Hou Lei |
| author_facet | Qiong Hu Gui-Shan Lin Wen-Gui Duan Min Huang Fu-Hou Lei |
| author_sort | Qiong Hu |
| collection | DOAJ |
| description | 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%. |
| first_indexed | 2024-12-11T22:15:15Z |
| format | Article |
| id | doaj.art-24a7c101b009447db29c64f4f63d3480 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T22:15:15Z |
| publishDate | 2017-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-24a7c101b009447db29c64f4f63d34802022-12-22T00:48:38ZengMDPI AGMolecules1420-30492017-10-012210167810.3390/molecules22101678molecules22101678Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime EstersQiong Hu0Gui-Shan Lin1Wen-Gui Duan2Min Huang3Fu-Hou Lei4School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, Guangxi, ChinaSchool of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, Guangxi, ChinaSchool of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, Guangxi, ChinaSchool of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, Guangxi, ChinaGuangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008, Guangxi, ChinaTwenty-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%.https://www.mdpi.com/1420-3049/22/10/1678α-pineneverbenoneoxime(Z)- and (E)-isomerantifungal activityherbicidal activity |
| spellingShingle | Qiong Hu Gui-Shan Lin Wen-Gui Duan Min Huang Fu-Hou Lei Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters Molecules α-pinene verbenone oxime (Z)- and (E)-isomer antifungal activity herbicidal activity |
| title | Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters |
| title_full | Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters |
| title_fullStr | Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters |
| title_full_unstemmed | Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters |
| title_short | Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters |
| title_sort | synthesis and biological activity of novel z and e verbenone oxime esters |
| topic | α-pinene verbenone oxime (Z)- and (E)-isomer antifungal activity herbicidal activity |
| url | https://www.mdpi.com/1420-3049/22/10/1678 |
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