Synthesis and Herbicidal Activity of 6-Alkoxy(aryloxy) Multisubstituted Pyridine Derivatives

doi:10.6023/cjoc201603026

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (9): 2225-2231.DOI: 10.6023/cjoc201603026 Previous Articles Next Articles

NOTE

含6-烷(芳)氧基多取代吡啶衍生物的合成与除草活性

刘建超^a, 任青云^b, 贺红武^a

a 华中师范大学化学学院武汉 430079;
b 广东东阳光药业研究院新药所抗感染原创部东莞 523871

收稿日期:2016-03-15 修回日期:2016-04-15 发布日期:2016-05-17
通讯作者: 任青云, 贺红武 E-mail:he1208@mail.ccnu.edu.cn;renqingyun@hecpharm.com
基金资助:
国家重点基础研究发展规划（973计划，No.2010CB126100）、国家自然科学基金（Nos.21172090，31000867）、教育部长江学者和创新团队发展计划（No.IRT0953）和湖北省自然科学基金重点（No.2014CFA111）资助项目.

Synthesis and Herbicidal Activity of 6-Alkoxy(aryloxy) Multisubstituted Pyridine Derivatives

Liu Jianchao^a, Ren Qingyun^b, He Hongwu^a

a College of Chemistry, Central China Normal University, Wuhan, 430079;
b Anti-infection Innovation Department, New Drug Research Institute, HEC Pharma Co., LTD, Dongguan 523871

Received:2016-03-15 Revised:2016-04-15 Published:2016-05-17
Supported by:
Project supported by the National Program on Key Basic Research Project (973 Program, No.2010CB126100), the National Natural Science Fundation of China (Nos.21172090, 31000867), the Program for Changjiang Scholars and Innovatives Research Team in University (No.IRT0953) and the Natural Science Foundation of Hubei Province (No.2014CFA111).

1. Synthesis and Herbicidal Activity of 6-Alkoxy(aryloxy) Multisubstituted Pyridine Derivatives.PDF(1414KB)

Abstract

Alkyl multisubstituted pyridine-2-yl sulfones have been designed and synthesized from 6-alkylthiopyridine using H₂O₂ and NaWO₃·2H₂O as catalysts in N,N-dimethylformamide (DMF). A series of new 6-alkoxy(aryloxy) multisubstituted pyridine derivatives have been synthesized from alkyl multisubstituted pyridine-2-yl sulfone and alcohol or phenol using K₂CO₃ (NaOC₂H₅ or NaOCH₃) as catalyst in CH₃CN. The structures of target compounds have been confirmed by ¹H NMR, ¹³C NMR, EI-MS, IR spectroscopy and elemental analysis. The structure of 4-amino-5-cyano-2-methyl-6-(3-nitryl phenoxy) nicotinic acid methyl ester has been determined by single crystal X-ray diffraction. The results of preliminary bioassay indicated that some compounds possess moderate herbicidal activities against the rape and barnyard grass and show obvious selectivity.

Key words: alkylthiopyridine, alkoxypyridine, nicotinic acid, NaWO₃·, 2H₂O, herbicidal activity

Cite this article

Liu Jianchao, Ren Qingyun, He Hongwu. Synthesis and Herbicidal Activity of 6-Alkoxy(aryloxy) Multisubstituted Pyridine Derivatives[J]. Chin. J. Org. Chem., 2016, 36(9): 2225-2231.

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含6-烷(芳)氧基多取代吡啶衍生物的合成与除草活性

Synthesis and Herbicidal Activity of 6-Alkoxy(aryloxy) Multisubstituted Pyridine Derivatives

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