Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives
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Multidisciplinary Digital Publishing Institute
2019-11-16
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| Subjects: | Organic synthesis, Natural products, Pesticides, Antiticks, Antifeedants, |
| Online Access: | http://hdl.handle.net/10261/195334 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003329 |
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dig-ica-es-10261-1953342021-12-27T15:55:41Z Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives Galisteo Pretel, Alberto Pérez del Pulgar, Helena Olmeda García, Ángeles Sonia González-Coloma, Azucena Barrero, Alejandro F. Quílez del Moral, José Francisco Ministerio de Economía y Competitividad (España) European Commission Organic synthesis Natural products Pesticides Antiticks Antifeedants © The Author(s). 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 SeO2, epoxidation with mCPBA, 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)3 as catalyst and dehydroxilation using the Grieco protocol. The insect antifeedant (against Myzus persicae and Ropaloshysum padi) and ixodicidal (against the tick Hyalomma lusitanicum) activities of these compounds were tested. Compound 20 was the most active substance against M. persicae and R. padi, and twice more efficient than nootkatone in the antitick test. This research was funded by Grant CTQ-2015-64049-C3-3-R / CTQ2015-64049-C3-1-R; Ministerio de Economía y Competitividad, Spain (MINECO/FEDER). Peer reviewed 2019-11-22T14:47:57Z 2019-11-22T14:47:57Z 2019-11-16 2019-11-22T14:47:58Z artículo http://purl.org/coar/resource_type/c_6501 Biomolecules 9(11): 742 (2019) 2218-273X http://hdl.handle.net/10261/195334 10.3390/biom9110742 2218-273X http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003329 31744055 #PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015-64049-C3-3-R info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015-64049-C3-1-R Publisher’s version https://doi.org/10.3390/biom9110742 Sí open Multidisciplinary Digital Publishing Institute |
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Organic synthesis Natural products Pesticides Antiticks Antifeedants Organic synthesis Natural products Pesticides Antiticks Antifeedants |
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Organic synthesis Natural products Pesticides Antiticks Antifeedants Organic synthesis Natural products Pesticides Antiticks Antifeedants Galisteo Pretel, Alberto Pérez del Pulgar, Helena Olmeda García, Ángeles Sonia González-Coloma, Azucena Barrero, Alejandro F. Quílez del Moral, José Francisco Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives |
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© The Author(s). |
| author2 |
Ministerio de Economía y Competitividad (España) |
| author_facet |
Ministerio de Economía y Competitividad (España) Galisteo Pretel, Alberto Pérez del Pulgar, Helena Olmeda García, Ángeles Sonia González-Coloma, Azucena Barrero, Alejandro F. Quílez del Moral, José Francisco |
| format |
artículo |
| topic_facet |
Organic synthesis Natural products Pesticides Antiticks Antifeedants |
| author |
Galisteo Pretel, Alberto Pérez del Pulgar, Helena Olmeda García, Ángeles Sonia González-Coloma, Azucena Barrero, Alejandro F. Quílez del Moral, José Francisco |
| author_sort |
Galisteo Pretel, Alberto |
| title |
Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives |
| title_short |
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_sort |
novel insect antifeedant and ixodicidal nootkatone derivatives |
| publisher |
Multidisciplinary Digital Publishing Institute |
| publishDate |
2019-11-16 |
| url |
http://hdl.handle.net/10261/195334 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003329 |
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