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New Insights into the Degradation Path of Deltamethrin
Pyrethroids are among the insecticidal compounds indicated by the World Health Organization for mitigation of vector-borne diseases. Active deltamethrin (with chiral configuration α-S,1-R-cis) is one of the most effective pyrethroids characterized by low toxicity to humans, and it is currently teste...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8270271/ https://www.ncbi.nlm.nih.gov/pubmed/34206625 http://dx.doi.org/10.3390/molecules26133811 |
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author | Aiello, Federica Simons, Marcel G. van Velde, Jan W. Dani, Paulo |
author_facet | Aiello, Federica Simons, Marcel G. van Velde, Jan W. Dani, Paulo |
author_sort | Aiello, Federica |
collection | PubMed |
description | Pyrethroids are among the insecticidal compounds indicated by the World Health Organization for mitigation of vector-borne diseases. Active deltamethrin (with chiral configuration α-S,1-R-cis) is one of the most effective pyrethroids characterized by low toxicity to humans, and it is currently tested as active ingredient for insecticidal paints. Nevertheless, several degradation processes can occur and affect the insecticidal efficacy in the complex paint matrix. In the present study, a detailed NMR analysis of deltamethrin stability has been carried out under stress conditions, mimicking a water-based insecticidal paint environment. Two novel by-products, having a diastereomeric relationship, were identified and their structure was elucidated by combining NMR, HPLC, GC-MS, and ESI-MS analyses. These compounds are the result from a nucleophilic addition involving deltamethrin and one of its major degradation products, 3-phenoxybenzaldehyde. Given the known toxicity of the aldehyde, this reaction could represent a way to reduce its concentration into the matrix. On the other hand, the toxicology of these compounds towards humans should be addressed, as their presence may adversely affect the performance of deltamethrin-containing products. |
format | Online Article Text |
id | pubmed-8270271 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-82702712021-07-10 New Insights into the Degradation Path of Deltamethrin Aiello, Federica Simons, Marcel G. van Velde, Jan W. Dani, Paulo Molecules Article Pyrethroids are among the insecticidal compounds indicated by the World Health Organization for mitigation of vector-borne diseases. Active deltamethrin (with chiral configuration α-S,1-R-cis) is one of the most effective pyrethroids characterized by low toxicity to humans, and it is currently tested as active ingredient for insecticidal paints. Nevertheless, several degradation processes can occur and affect the insecticidal efficacy in the complex paint matrix. In the present study, a detailed NMR analysis of deltamethrin stability has been carried out under stress conditions, mimicking a water-based insecticidal paint environment. Two novel by-products, having a diastereomeric relationship, were identified and their structure was elucidated by combining NMR, HPLC, GC-MS, and ESI-MS analyses. These compounds are the result from a nucleophilic addition involving deltamethrin and one of its major degradation products, 3-phenoxybenzaldehyde. Given the known toxicity of the aldehyde, this reaction could represent a way to reduce its concentration into the matrix. On the other hand, the toxicology of these compounds towards humans should be addressed, as their presence may adversely affect the performance of deltamethrin-containing products. MDPI 2021-06-22 /pmc/articles/PMC8270271/ /pubmed/34206625 http://dx.doi.org/10.3390/molecules26133811 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Aiello, Federica Simons, Marcel G. van Velde, Jan W. Dani, Paulo New Insights into the Degradation Path of Deltamethrin |
title | New Insights into the Degradation Path of Deltamethrin |
title_full | New Insights into the Degradation Path of Deltamethrin |
title_fullStr | New Insights into the Degradation Path of Deltamethrin |
title_full_unstemmed | New Insights into the Degradation Path of Deltamethrin |
title_short | New Insights into the Degradation Path of Deltamethrin |
title_sort | new insights into the degradation path of deltamethrin |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8270271/ https://www.ncbi.nlm.nih.gov/pubmed/34206625 http://dx.doi.org/10.3390/molecules26133811 |
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