The discovery of 3-(1-aminoethylidene)quinoline-2, 4(1H,3H)-dione derivatives as novel PSII electron transport inhibitors.
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 g ha−1 or lower. The symptom of injured leaves in vivo, the high Hill reaction inhibitory activity of 6h in vitro(IC50 0.1μgmL−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.
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, People's Republic of China.
Yu-Xiu
YX
Liu
Hua-Ping
HP
Zhao
Zi-Wen
ZW
Wang
Yong-Hong
YH
Li
Hai-Bin
HB
Song
Hannah
H
Riches
David
D
Beattie
Yu-Cheng
YC
Gu
Qing-Min
QM
Wang
D001665:Binding Sites; D004579:Electron Transport / Q000187:drug effects*; D006540:Herbicides / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D010641:Phenotype; D010788:Photosynthesis / Q000187:drug effects*; D010944:Plants / Q000187:drug effects; D011485:Protein Binding; D011804:Quinolines / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D006540:Herbicides; D011804:Quinolines