Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (7): 1506-1513.DOI: 10.6023/cjoc201501040 Previous Articles     Next Articles



张浩a, 刘瑞全a, 李奇博a, 李青阳a, 陈亚红b, 刘克昌a, 刘尚钟a   

  1. a 中国农业大学理学院应用化学系 北京 100193;
    b 北京颖泰嘉和生物科技有限公司 北京 100192
  • 收稿日期:2015-01-29 修回日期:2015-02-28 发布日期:2015-07-24
  • 通讯作者: 刘尚钟
  • 基金资助:

    “十二五”科技支撑计划(No. 2011BAE06B03)、国家自然科学基金(No. 21172256)资助项目.

Synthesis and Herbicidal Activities of N-Substituted Pyridyl-2- acyltetrahydropyridazine-1(2H)-carbothioamides

Zhang Haoa, Liu Ruiquana, Li Qiboa, Li Qingyanga, Chen Yahongb, Liu Kechanga, Liu Shangzhonga   

  1. a Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193;
    b Nutrichem Co., Ltd, Beijing 100192
  • Received:2015-01-29 Revised:2015-02-28 Published:2015-07-24
  • Supported by:

    Project supported by the National Key Technologies R&D Program (No. 2011BAE06B03), and the National Natural Science Foundation of China (No. 21172256).

Key intermediates-substituted pyridyl isothiocyanates, which were prepared from starting material substituted pyridyl amines via two steps, were further condensed with four substituted hexahydropyridazine intermediates to afford four series of novel N-substituted pyridyl-2-acyltetrahydropyridazine-1(2H)-carbothioamides 811. The structures of all compounds have been confirmed by 1H NMR, 13C NMR and HRMS techniques. The preliminary bioassay results indicated that some of the title compounds exhibited approximately 100% inhibition against Abutilon theophrasti, Amaranthus retroflexus and Digitaria sanguinalis at a dose of 375 g·ha-1. In particular, ethyl 2-((5-chloropyridin-2-yl)carbamothioyl)tetrahydropy- ridazine-1(2H)-carboxylate (9e) displayed the best pre-emergence herbicidal effect against Abutilon theophrasti with 95% inhibitory activity even at 45 g·ha-1.

Key words: acyl thiosemicarbazides, hexahydropyridazine, pyridine, synthesis, herbicidal activity