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Synthesis and Biological Activity Evaluation of Novel β-Substituted Nitromethylene Neonicotinoid Analogues
The structure-based design and synthesis of a series of novel neonicotinoid analogues are described. The novel neonicotinoid analogues were designed based upon the reaction of enamine derivatives with electron-withdrawing β-substituents with electrophilic thiocyanogen reagents. These compounds were...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268173/ https://www.ncbi.nlm.nih.gov/pubmed/22922273 http://dx.doi.org/10.3390/molecules170910014 |
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author | Wang, Baozhu Cheng, Jiagao Xu, Zhiping Xu, Xiaoyong Shao, Xusheng Li, Zhong |
author_facet | Wang, Baozhu Cheng, Jiagao Xu, Zhiping Xu, Xiaoyong Shao, Xusheng Li, Zhong |
author_sort | Wang, Baozhu |
collection | PubMed |
description | The structure-based design and synthesis of a series of novel neonicotinoid analogues are described. The novel neonicotinoid analogues were designed based upon the reaction of enamine derivatives with electron-withdrawing β-substituents with electrophilic thiocyanogen reagents. These compounds were characterized by spectroscopic methods. Bioassays indicated that some of the synthesized compounds exhibited excellent bioactivity against cowpea aphids (Aphis craccivora). The LC(50) values of compounds 7, 9, 12, 13, 15, 17, 19, 20 and commercial imidacloprid were 0.01567, 0.00974, 0.02494, 0.01893, 0.02677, 0.01778, 0.0220, 0.02447 and 0.03502 mmol L(−1), respectively, which suggested that they could be used as leads for future development of new insecticides. |
format | Online Article Text |
id | pubmed-6268173 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62681732018-12-12 Synthesis and Biological Activity Evaluation of Novel β-Substituted Nitromethylene Neonicotinoid Analogues Wang, Baozhu Cheng, Jiagao Xu, Zhiping Xu, Xiaoyong Shao, Xusheng Li, Zhong Molecules Article The structure-based design and synthesis of a series of novel neonicotinoid analogues are described. The novel neonicotinoid analogues were designed based upon the reaction of enamine derivatives with electron-withdrawing β-substituents with electrophilic thiocyanogen reagents. These compounds were characterized by spectroscopic methods. Bioassays indicated that some of the synthesized compounds exhibited excellent bioactivity against cowpea aphids (Aphis craccivora). The LC(50) values of compounds 7, 9, 12, 13, 15, 17, 19, 20 and commercial imidacloprid were 0.01567, 0.00974, 0.02494, 0.01893, 0.02677, 0.01778, 0.0220, 0.02447 and 0.03502 mmol L(−1), respectively, which suggested that they could be used as leads for future development of new insecticides. MDPI 2012-08-24 /pmc/articles/PMC6268173/ /pubmed/22922273 http://dx.doi.org/10.3390/molecules170910014 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Wang, Baozhu Cheng, Jiagao Xu, Zhiping Xu, Xiaoyong Shao, Xusheng Li, Zhong Synthesis and Biological Activity Evaluation of Novel β-Substituted Nitromethylene Neonicotinoid Analogues |
title | Synthesis and Biological Activity Evaluation of Novel β-Substituted Nitromethylene Neonicotinoid Analogues |
title_full | Synthesis and Biological Activity Evaluation of Novel β-Substituted Nitromethylene Neonicotinoid Analogues |
title_fullStr | Synthesis and Biological Activity Evaluation of Novel β-Substituted Nitromethylene Neonicotinoid Analogues |
title_full_unstemmed | Synthesis and Biological Activity Evaluation of Novel β-Substituted Nitromethylene Neonicotinoid Analogues |
title_short | Synthesis and Biological Activity Evaluation of Novel β-Substituted Nitromethylene Neonicotinoid Analogues |
title_sort | synthesis and biological activity evaluation of novel β-substituted nitromethylene neonicotinoid analogues |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268173/ https://www.ncbi.nlm.nih.gov/pubmed/22922273 http://dx.doi.org/10.3390/molecules170910014 |
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