Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives
Naturally occurring nootkatone, with reported insecticidal and acaricidal properties, has been used as a lead to generate molecular diversity and, consequently, new insect antifeedant and ixodicidal compounds. A total of 22 derivatives were generated by subjecting this molecule to several reactions...
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MDPI AG
2019-11-01
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| Series: | Biomolecules |
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| Online Access: | https://www.mdpi.com/2218-273X/9/11/742 |
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| author | Alberto Galisteo Pretel Helena Pérez del Pulgar A. Sonia Olmeda Azucena Gonzalez-Coloma Alejandro F. Barrero José Francisco Quílez del Moral |
| author_facet | Alberto Galisteo Pretel Helena Pérez del Pulgar A. Sonia Olmeda Azucena Gonzalez-Coloma Alejandro F. Barrero José Francisco Quílez del Moral |
| author_sort | Alberto Galisteo Pretel |
| collection | DOAJ |
| description | Naturally occurring nootkatone, with reported insecticidal and acaricidal properties, has been used as a lead to generate molecular diversity and, consequently, new insect antifeedant and ixodicidal compounds. A total of 22 derivatives were generated by subjecting this molecule to several reactions including dehydrogenation with the iodine/DMSO system, oxidation with SeO<sub>2</sub>, epoxidation with <i>m</i>CPBA, oxidation or carbon homologations of the α-carbonyl position with TMSOTf (trimethylsilyl trifluoromethanesulfonate) followed by Rubottom and Dess Martin periodane oxidations, condensation with formaldehyde using Yb(OTf)<sub>3</sub> as catalyst and dehydroxilation using the Grieco protocol. The insect antifeedant (against <i>Myzus persicae</i> and <i>Ropaloshysum padi</i>) and ixodicidal (against the tick <i>Hyalomma lusitanicum</i>) activities of these compounds were tested. Compound <b>20</b> was the most active substance against <i>M. persicae</i> and <i>R. padi</i>, and twice more efficient than nootkatone in the antitick test. |
| first_indexed | 2024-12-14T00:20:41Z |
| format | Article |
| id | doaj.art-c52ecfa845f74d55841ce0d3bbdb5935 |
| institution | Directory Open Access Journal |
| issn | 2218-273X |
| language | English |
| last_indexed | 2024-12-14T00:20:41Z |
| publishDate | 2019-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomolecules |
| spelling | doaj.art-c52ecfa845f74d55841ce0d3bbdb59352022-12-21T23:25:15ZengMDPI AGBiomolecules2218-273X2019-11-0191174210.3390/biom9110742biom9110742Novel Insect Antifeedant and Ixodicidal Nootkatone DerivativesAlberto Galisteo Pretel0Helena Pérez del Pulgar1A. Sonia Olmeda2Azucena Gonzalez-Coloma3Alejandro F. Barrero4José Francisco Quílez del Moral5Department of Organic Chemistry, Institute of Biotechnology, University of Granada, 18071 Granada, SpainDepartment of Organic Chemistry, Institute of Biotechnology, University of Granada, 18071 Granada, SpainFaculty of Veterinary, Complutense University of Madrid (UCM), 28040 Madrid, SpainInstitute of Agricultural Sciences, CSIC, 28006, Madrid, SpainDepartment of Organic Chemistry, Institute of Biotechnology, University of Granada, 18071 Granada, SpainDepartment of Organic Chemistry, Institute of Biotechnology, University of Granada, 18071 Granada, SpainNaturally occurring nootkatone, with reported insecticidal and acaricidal properties, has been used as a lead to generate molecular diversity and, consequently, new insect antifeedant and ixodicidal compounds. A total of 22 derivatives were generated by subjecting this molecule to several reactions including dehydrogenation with the iodine/DMSO system, oxidation with SeO<sub>2</sub>, epoxidation with <i>m</i>CPBA, oxidation or carbon homologations of the α-carbonyl position with TMSOTf (trimethylsilyl trifluoromethanesulfonate) followed by Rubottom and Dess Martin periodane oxidations, condensation with formaldehyde using Yb(OTf)<sub>3</sub> as catalyst and dehydroxilation using the Grieco protocol. The insect antifeedant (against <i>Myzus persicae</i> and <i>Ropaloshysum padi</i>) and ixodicidal (against the tick <i>Hyalomma lusitanicum</i>) activities of these compounds were tested. Compound <b>20</b> was the most active substance against <i>M. persicae</i> and <i>R. padi</i>, and twice more efficient than nootkatone in the antitick test.https://www.mdpi.com/2218-273X/9/11/742organic synthesisnatural productspesticidesantiticksantifeedant |
| spellingShingle | Alberto Galisteo Pretel Helena Pérez del Pulgar A. Sonia Olmeda Azucena Gonzalez-Coloma Alejandro F. Barrero José Francisco Quílez del Moral Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives Biomolecules organic synthesis natural products pesticides antiticks antifeedant |
| title | Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives |
| title_full | Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives |
| title_fullStr | Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives |
| title_full_unstemmed | Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives |
| title_short | Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives |
| title_sort | novel insect antifeedant and ixodicidal nootkatone derivatives |
| topic | organic synthesis natural products pesticides antiticks antifeedant |
| url | https://www.mdpi.com/2218-273X/9/11/742 |
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