Synthesis of Piperine-Based Ester Derivatives with Diverse Aromatic Rings and Their Agricultural Bioactivities against <i>Tetranychus cinnabarinus</i> Boisduval, <i>Aphis citricola</i> Van der Goot, and <i>Eriosoma lanigerum</i> Hausmann
Exploration of plant secondary metabolites or by using them as leads for development of new pesticides has become one of the focal research topics nowadays. Herein, a series of new ester derivatives of piperine were prepared via the Vilsmeier–Haack–Arnold (VHA) reaction, and their structures were ch...
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| Format: | Article |
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MDPI AG
2022-12-01
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| Series: | Insects |
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| Online Access: | https://www.mdpi.com/2075-4450/14/1/40 |
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| author | Tianze Li Min Lv Houpeng Wen Yanyan Wang Sunita Thapa Shaoyong Zhang Hui Xu |
| author_facet | Tianze Li Min Lv Houpeng Wen Yanyan Wang Sunita Thapa Shaoyong Zhang Hui Xu |
| author_sort | Tianze Li |
| collection | DOAJ |
| description | Exploration of plant secondary metabolites or by using them as leads for development of new pesticides has become one of the focal research topics nowadays. Herein, a series of new ester derivatives of piperine were prepared via the Vilsmeier–Haack–Arnold (VHA) reaction, and their structures were characterized by infrared spectroscopy (IR), melting point (mp), proton nuclear magnetic resonance spectroscopy (<sup>1</sup>H NMR), and carbon nuclear magnetic resonance spectroscopy (<sup>13</sup>C NMR). Notably, the steric configurations of compounds <b>6</b> and <b>7</b> were confirmed by single-crystal analysis. Against <i>T. cinnabarinus</i>, compounds <b>9</b> and <b>11</b> exhibited 47.6- and 45.4-fold more pronounced acaricidal activity than piperine. In particular, compounds <b>9</b> and <b>11</b> also showed 2.6-fold control efficiency on the fifth day of piperine. In addition, compound <b>6</b> (>10–fold higher than piperine) displayed the most potent aphicidal activity against <i>A. citricola</i>. Furthermore, some derivatives showed good aphicidal activities against <i>E. lanigerum</i>. Moreover, the effects of compounds on the cuticles of <i>T. cinnabarinus</i> were investigated by the scanning electron microscope (SEM) imaging method. This study will pave the way for future high value added application of piperine and its derivatives as botanical pesticides. |
| first_indexed | 2024-03-09T12:14:56Z |
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| institution | Directory Open Access Journal |
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| language | English |
| last_indexed | 2024-03-09T12:14:56Z |
| publishDate | 2022-12-01 |
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| series | Insects |
| spelling | doaj.art-84a08e6a19b64b02b8298e4df2e876542023-11-30T22:48:07ZengMDPI AGInsects2075-44502022-12-011414010.3390/insects14010040Synthesis of Piperine-Based Ester Derivatives with Diverse Aromatic Rings and Their Agricultural Bioactivities against <i>Tetranychus cinnabarinus</i> Boisduval, <i>Aphis citricola</i> Van der Goot, and <i>Eriosoma lanigerum</i> HausmannTianze Li0Min Lv1Houpeng Wen2Yanyan Wang3Sunita Thapa4Shaoyong Zhang5Hui Xu6College of Plant Protection, Northwest A&F University, Xianyang 712100, ChinaCollege of Plant Protection, Northwest A&F University, Xianyang 712100, ChinaCollege of Plant Protection, Northwest A&F University, Xianyang 712100, ChinaCollege of Plant Protection, Northwest A&F University, Xianyang 712100, ChinaCollege of Plant Protection, Northwest A&F University, Xianyang 712100, ChinaKey Laboratory of Vector Biology and Pathogen Control of Zhejiang Province, College of Life Science, Huzhou University, Huzhou 313000, ChinaCollege of Plant Protection, Northwest A&F University, Xianyang 712100, ChinaExploration of plant secondary metabolites or by using them as leads for development of new pesticides has become one of the focal research topics nowadays. Herein, a series of new ester derivatives of piperine were prepared via the Vilsmeier–Haack–Arnold (VHA) reaction, and their structures were characterized by infrared spectroscopy (IR), melting point (mp), proton nuclear magnetic resonance spectroscopy (<sup>1</sup>H NMR), and carbon nuclear magnetic resonance spectroscopy (<sup>13</sup>C NMR). Notably, the steric configurations of compounds <b>6</b> and <b>7</b> were confirmed by single-crystal analysis. Against <i>T. cinnabarinus</i>, compounds <b>9</b> and <b>11</b> exhibited 47.6- and 45.4-fold more pronounced acaricidal activity than piperine. In particular, compounds <b>9</b> and <b>11</b> also showed 2.6-fold control efficiency on the fifth day of piperine. In addition, compound <b>6</b> (>10–fold higher than piperine) displayed the most potent aphicidal activity against <i>A. citricola</i>. Furthermore, some derivatives showed good aphicidal activities against <i>E. lanigerum</i>. Moreover, the effects of compounds on the cuticles of <i>T. cinnabarinus</i> were investigated by the scanning electron microscope (SEM) imaging method. This study will pave the way for future high value added application of piperine and its derivatives as botanical pesticides.https://www.mdpi.com/2075-4450/14/1/40piperineester<i>Tetranychus cinnabarinus</i> Boisduval<i>Aphis citricola</i> Van der Goot<i>Eriosoma lanigerum</i> Hausmannstructural modification |
| spellingShingle | Tianze Li Min Lv Houpeng Wen Yanyan Wang Sunita Thapa Shaoyong Zhang Hui Xu Synthesis of Piperine-Based Ester Derivatives with Diverse Aromatic Rings and Their Agricultural Bioactivities against <i>Tetranychus cinnabarinus</i> Boisduval, <i>Aphis citricola</i> Van der Goot, and <i>Eriosoma lanigerum</i> Hausmann Insects piperine ester <i>Tetranychus cinnabarinus</i> Boisduval <i>Aphis citricola</i> Van der Goot <i>Eriosoma lanigerum</i> Hausmann structural modification |
| title | Synthesis of Piperine-Based Ester Derivatives with Diverse Aromatic Rings and Their Agricultural Bioactivities against <i>Tetranychus cinnabarinus</i> Boisduval, <i>Aphis citricola</i> Van der Goot, and <i>Eriosoma lanigerum</i> Hausmann |
| title_full | Synthesis of Piperine-Based Ester Derivatives with Diverse Aromatic Rings and Their Agricultural Bioactivities against <i>Tetranychus cinnabarinus</i> Boisduval, <i>Aphis citricola</i> Van der Goot, and <i>Eriosoma lanigerum</i> Hausmann |
| title_fullStr | Synthesis of Piperine-Based Ester Derivatives with Diverse Aromatic Rings and Their Agricultural Bioactivities against <i>Tetranychus cinnabarinus</i> Boisduval, <i>Aphis citricola</i> Van der Goot, and <i>Eriosoma lanigerum</i> Hausmann |
| title_full_unstemmed | Synthesis of Piperine-Based Ester Derivatives with Diverse Aromatic Rings and Their Agricultural Bioactivities against <i>Tetranychus cinnabarinus</i> Boisduval, <i>Aphis citricola</i> Van der Goot, and <i>Eriosoma lanigerum</i> Hausmann |
| title_short | Synthesis of Piperine-Based Ester Derivatives with Diverse Aromatic Rings and Their Agricultural Bioactivities against <i>Tetranychus cinnabarinus</i> Boisduval, <i>Aphis citricola</i> Van der Goot, and <i>Eriosoma lanigerum</i> Hausmann |
| title_sort | synthesis of piperine based ester derivatives with diverse aromatic rings and their agricultural bioactivities against i tetranychus cinnabarinus i boisduval i aphis citricola i van der goot and i eriosoma lanigerum i hausmann |
| topic | piperine ester <i>Tetranychus cinnabarinus</i> Boisduval <i>Aphis citricola</i> Van der Goot <i>Eriosoma lanigerum</i> Hausmann structural modification |
| url | https://www.mdpi.com/2075-4450/14/1/40 |
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