Design, synthesis and biological activity of novel triketone herbicides containing natural product fragments

被引:11
|
作者
Jiang, Zi-Bin [1 ]
Gao, Shuang [1 ]
Hu, Wei [1 ]
Sheng, Bo-Ren [1 ]
Shi, Juan [1 ]
Ye, Fei [1 ]
Fu, Ying [1 ]
机构
[1] Northeast Agr Univ, Coll Arts & Sci, Dept Chem, Harbin 150030, Peoples R China
基金
中国国家自然科学基金;
关键词
HPPD; Synthesis; Coumarin fragment; Herbicidal activity; Molecular modeling; P-HYDROXYPHENYLPYRUVATE DIOXYGENASE; 4-HYDROXYPHENYLPYRUVATE DIOXYGENASE; MOLECULAR DOCKING; DERIVATIVES; INHIBITORS; DISCOVERY;
D O I
10.1016/j.pestbp.2023.105493
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) belongs to the non-heme Fe2+ -containing enzyme family and is an important enzyme in tyrosine decomposition. HPPD is crucial to the discovery of novel bleaching herbicides. To develop novel HPPD inhibitor herbicides containing the & beta;-triketone motif, a series of 4-hydroxyl-3-(substituted aryl)-pyran-2-one derivatives were designed using the active fragment splicing method. The title compounds were synthesized and characterized through infrared spectroscopy (IR), 1H nuclear mag-netic resonance (1H NMR), 13C nuclear magnetic resonance (13C NMR), and high-resolution mass spectrometry (HRMS). The X-ray diffraction method determined the single crystal structure of I-17. Preliminary bioassay data revealed that several novel compounds, especially I-12 and II-3, showed excellent herbicidal activity against broadleaf and monocotyledonous weeds at a dose of 150 g ai/ha. The results of crop selectivity and carotenoids determination indicated that compound I-12 is more suitable for wheat and cotton fields than mesotrione. Additionally, compound II-3 is safer for soybeans and peanuts than mesotrione. The inhibitory activity of Ara-bidopsis thaliana HPPD (AtHPPD) verified that compound II-3 showed the most activity with an IC50 value of 0.248 & mu;M, which was superior to that of mesotrione (0.283 & mu;M) in vitro. The binding mode of compound II-3 and AtHPPD was confirmed through molecular docking and molecular dynamics simulations. This study provides insights into the future development of natural and efficient herbicides.
引用
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页数:11
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