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-<i>S</i>,1-<i>R</i>-<i>cis</i>) is one of the most effective pyrethroids character...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/13/3811 |
| _version_ | 1797529174682894336 |
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| author | Federica Aiello Marcel G. Simons Jan W. van Velde Paulo Dani |
| author_facet | Federica Aiello Marcel G. Simons Jan W. van Velde Paulo Dani |
| author_sort | Federica Aiello |
| collection | DOAJ |
| 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-<i>S</i>,1-<i>R</i>-<i>cis</i>) 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. |
| first_indexed | 2024-03-10T10:10:00Z |
| format | Article |
| id | doaj.art-b1897fbf80964672a9a7486b1e76e7eb |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T10:10:00Z |
| publishDate | 2021-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-b1897fbf80964672a9a7486b1e76e7eb2023-11-22T01:15:51ZengMDPI AGMolecules1420-30492021-06-012613381110.3390/molecules26133811New Insights into the Degradation Path of DeltamethrinFederica Aiello0Marcel G. Simons1Jan W. van Velde2Paulo Dani3ECG-MAS, Expert Capability Group—Measurement and Analytical Science, Nouryon B.V., 7418 Deventer, The NetherlandsECG-MAS, Expert Capability Group—Measurement and Analytical Science, Nouryon B.V., 7418 Deventer, The NetherlandsECG-MAS, Expert Capability Group—Measurement and Analytical Science, Nouryon B.V., 7418 Deventer, The NetherlandsECG-MAS, Expert Capability Group—Measurement and Analytical Science, Nouryon B.V., 7418 Deventer, The NetherlandsPyrethroids are among the insecticidal compounds indicated by the World Health Organization for mitigation of vector-borne diseases. Active deltamethrin (with chiral configuration α-<i>S</i>,1-<i>R</i>-<i>cis</i>) 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.https://www.mdpi.com/1420-3049/26/13/3811NMR spectroscopyanalyticsdeltamethrininsecticidal paints |
| spellingShingle | Federica Aiello Marcel G. Simons Jan W. van Velde Paulo Dani New Insights into the Degradation Path of Deltamethrin Molecules NMR spectroscopy analytics deltamethrin insecticidal paints |
| 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 | NMR spectroscopy analytics deltamethrin insecticidal paints |
| url | https://www.mdpi.com/1420-3049/26/13/3811 |
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