Citation: Dai Hong, Chen Jia, Hong Yu, Yuan Binying, Chen Yumeng, Shi Yujun, Ma Ruiyuan, Liang Zhipeng, Shi Jian. Synthesis and Herbicidal Activity of Novel Cyanoacrylates Containing Substituted Pyridyl Moiety[J]. Chinese Journal of Organic Chemistry, ;2017, 37(3): 739-745. doi: 10.6023/cjoc201611029 shu

Synthesis and Herbicidal Activity of Novel Cyanoacrylates Containing Substituted Pyridyl Moiety

Dai Hong ^a ,
Chen Jia ^a ,
Hong Yu ^a ,
Yuan Binying ^a ,
Chen Yumeng ^a ,
Shi Yujun ^a,*,, ,
Ma Ruiyuan ^a ,
Liang Zhipeng ^b ,
Shi Jian ^b,*,,

a.
College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019
b.
Analysis and Testing Center, Nantong University, Nantong 226019

Corresponding author: Shi Yujun, yjshi2015@163.com Shi Jian, gaohbhe2015@aliyun.com
Received Date: 23 November 2016
Revised Date: 8 December 2016

Fund Project: the Research Foundation of the Six People Peak of Jiangsu Province 2013-SWYY-013the National Natural Science Foundation of China 21372135the Science and Technology Innovation Foundation for the College Students of Jiangsu Province 201610304047Z

Figures(1)

In order to find new cyanoacrylate lead compounds, a series of novel cyanoacrylates containing substituted pyridyl moiety were prepared by the method of active substructure combination. The structures of the target compounds were confirmed by ¹H NMR, ¹³C NMR and elemental analyses. Preliminary bioassay data displayed that in postemergence treatment 2-cyano-3-methylthio-3-[4-(5-trifluoromethylpyridyl-2-amino)]benzylamino (2-methoxy) ethyl ester (7l) had 95% herbicidal activity against Brassica juncea at 1500 g/ha and 2-cyano-3-methylthio-3-[4-(5-trifluoromethylpyridyl-2-amino)]benzylamino-[2-(2, 4-difluorophenoxy)]ethyl ester (7e), 7l and 2-cyano-3-methylthio-3-[4-(5-trifluoromethylpyridyl-2-amino)]benzylamino-(2-ethoxy) ethyl ester (7m) showed 80%, 80% and 100% herbicidal activity against Stellaria media, respectively. Additionally, 2-cyano-3-methylthio-3-[4-(5-trifluoromethylpyridyl-2-amino)]benzylamino[2-(2-fluorophenoxy)]ethyl ester (7b), 7l and 7m all exhibited 100% herbicidal activity against Chenopodium serotinum L. at 1500 g/ha.
- pyridine,
- cyanoacrylate,
- synthesis,
- herbicidal activity
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