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Design, synthesis and insecticidal activities of dihydropyridine-fused neonicotinoids compounds with trifluoromethyl group

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Abstract

A series of novel neonicotinoids containing a dihydro-pyridine ring and a trifluoromethyl group were designed and synthesized by multicomponent reactions of 6-Cl-PMNI, triethoxymethane and 4,4,4-trifluoro-3-oxobutaneanilides (9) under solvent-free and catalyst-free conditions. The trifluoromethyl group plays an important role as an electron-withdrawing group in enhancing the reaction activity of compound 9. The target compounds were characterized by 1H NMR, IR and elemental analysis. Bioassays indicated that most of the synthesized compounds exhibited moderate insecticidal activities against Aphis craccivora.

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Acknowledgment

This work was financial supported by the National Science Foundation China Program (Grant 20902037), the Opening Project of Shanghai Key Laboratory of Chemical Biology.

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Authors and Affiliations

  1. Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, No. 336, West Road of Nan Xinzhuang, Jinan, 250022, People’s Republic of China

    Zhongzhen Tian, Shuxia Cui & Li Dongmei

  2. Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai, 200237, People’s Republic of China

    Zhiping Xu

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  1. Zhongzhen Tian
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  2. Shuxia Cui
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  3. Li Dongmei
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  4. Zhiping Xu
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Correspondence to Zhongzhen Tian.

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Tian, Z., Cui, S., Dongmei, L. et al. Design, synthesis and insecticidal activities of dihydropyridine-fused neonicotinoids compounds with trifluoromethyl group. Res Chem Intermed 41, 7437–7447 (2015). https://doi.org/10.1007/s11164-014-1835-y

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  • DOI: https://doi.org/10.1007/s11164-014-1835-y

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