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Molecules 2012, 17(9), 10014-10025; doi:10.3390/molecules170910014

Synthesis and Biological Activity Evaluation of Novel β-Substituted Nitromethylene Neonicotinoid Analogues

Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, P.O. Box 544, 130 Meilong Road, Shanghai 200237, China
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Received: 25 June 2012 / Revised: 13 August 2012 / Accepted: 14 August 2012 / Published: 24 August 2012
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Abstract

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 LC50 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.
Keywords: neonicotinoid analogues; new design strategy; thiocyanogen; insecticidal activities neonicotinoid analogues; new design strategy; thiocyanogen; insecticidal activities
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Wang, B.; Cheng, J.; Xu, Z.; Xu, X.; Shao, X.; Li, Z. Synthesis and Biological Activity Evaluation of Novel β-Substituted Nitromethylene Neonicotinoid Analogues. Molecules 2012, 17, 10014-10025.

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