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

doi:10.6023/cjoc201501040

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

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N-取代吡啶基-2-酰基四氢哒嗪-1(2H)-硫代甲酰胺的合成及除草活性

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

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 E-mail:shangzho@cau.edu.cn
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 Hao^a, Liu Ruiquan^a, Li Qibo^a, Li Qingyang^a, Chen Yahong^b, Liu Kechang^a, Liu Shangzhong^a

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).

1. Synthesis and Herbicidal Activities of N-Substituted Pyridyl-2- acyltetrahydropyridazine-1(2H)-carbothioamides.PDF(1525KB)

Abstract

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 8～11. 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

Cite this article

Zhang Hao, Liu Ruiquan, Li Qibo, Li Qingyang, Chen Yahong, Liu Kechang, Liu Shangzhong. Synthesis and Herbicidal Activities of N-Substituted Pyridyl-2- acyltetrahydropyridazine-1(2H)-carbothioamides[J]. Chin. J. Org. Chem., 2015, 35(7): 1506-1513.

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N-取代吡啶基-2-酰基四氢哒嗪-1(2H)-硫代甲酰胺的合成及除草活性

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

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