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

doi:10.3390/molecules170910014

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

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

Baozhu Wang, Jiagao Cheng, Zhiping Xu, Xiaoyong Xu, Xusheng Shao and Zhong Li*

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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Cite This Article

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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