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

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
* Author to whom correspondence should be addressed.
Received: 25 June 2012; in revised form: 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

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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.

AMA 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(9):10014-10025.

Chicago/Turabian Style

Wang, Baozhu; Cheng, Jiagao; Xu, Zhiping; Xu, Xiaoyong; Shao, Xusheng; Li, Zhong. 2012. "Synthesis and Biological Activity Evaluation of Novel β-Substituted Nitromethylene Neonicotinoid Analogues." Molecules 17, no. 9: 10014-10025.

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