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The discovery of 3-(1-aminoethylidene)quinoline-2, 4(1H,3H)-dione derivatives as novel PSII electron transport inhibitors

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Abstract

Based on the structures of the 4-hydroxyphenylpyruvate dioxygenase inhibitor mesotrione and natural product fischerellin A, a series of imine derivatives of (\(E\))-3-acyl-quinoline-2,4(1H,3H)-dione (6, 12 and 16) were designed, synthesized and systematically evaluated for their herbicidal activity. The bioassay results indicated that most of the synthesized compounds displayed good to excellent herbicidal activity, of which 6e, 6g, 6h, 6q and 6t exhibited more than 50 % inhibition against Brassica napus L., Amaranthus retroflexu or Digitaria adscendens at a dosage of \(94\,\hbox {g}\,\hbox {ha}^{-1}\) or lower. The symptom of injured leaves in vivo, the high Hill reaction inhibitory activity of 6h in vitro (\(\hbox {IC}_{50}\,0.1\, \upmu \hbox {g}\,\hbox {mL}^{-1})\) and the computer-based binding model of compound 6h with D1 protein in photosystem II (PSII) reaction centre suggest this novel structure to likely be a new type of PSII electron transport inhibitor. Thus, we have found a novel type of diketone enamine structure targeted at the PSII reaction centre.

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Acknowledgments

This work was supported by the National Key Project for Basic Research (2010CB126106) and the National Natural Science Foundation of China (21121002, 21072109) and the National Key Technology Research and Development Program (2011BAE06B05-3).

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Authors and Affiliations

  1. State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, People’s Republic of China

    Yu-Xiu Liu, Hua-Ping Zhao, Zi-Wen Wang, Yong-Hong Li, Hai-Bin Song & Qing-Min Wang

  2. Syngenta Jealott’s Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, UK

    Hannah Riches, David Beattie & Yu-Cheng Gu

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  1. Yu-Xiu Liu
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Correspondence to Qing-Min Wang.

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Liu, YX., Zhao, HP., Wang, ZW. et al. The discovery of 3-(1-aminoethylidene)quinoline-2, 4(1H,3H)-dione derivatives as novel PSII electron transport inhibitors. Mol Divers 17, 701–710 (2013). https://doi.org/10.1007/s11030-013-9466-6

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