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
1. [1]
  Liu, X.; Huang, R. Q.; Cheng, M. R.; Zhao, Y. G.; Li, Z. G. Chem. J. Chin. Univ. 1999, 20, 1404 (in Chinese).
2. [2]
  Zou, X. M.; Yu, L. M.; Gao, Y.; Shi, H. L.; Fei, J.; Liu, B.; Li, H. F.; Hu, F. Z.; Yang, H. Z. Chin. J. Org. Chem. 2006, 26, 337 (in Chinese).
3. [3]
  Zhang, H.; Li, X. Y.; Hu, D. Y.; Yang, S.; Fan, H. T.; Wei, X.; Song, B. A. Chin. J. Org. Chem. 2011, 31, 1419 (in Chinese).
4. [4]
  Zhong, S. H.; Wang, C. F.; Song, Q. X.; Fan, M. L.; Liu, B. Y.; Wei, D. M.; Liu, J. B. Chin. J. Org. Chem. 2014, 34, 2324 (in Chinese). doi: 10.6023/cjoc201404020
5. [5]
  Wu, S. S.; Miao, W. K.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2015, 35, 1484 (in Chinese). doi: 10.6023/cjoc201412025
6. [6]
  Sun, H. K.; Wang, Q. M.; Huang, R. Q.; Li, H.; Li, Y. H. J. Organomet. Chem. 2002, 655, 182. doi: 10.1016/S0022-328X(02)01553-X
7. [7]
  Song, B. A.; Zhang, H. P.; Wang, H.; Yang, S.; Jin, L. H.; Hu, D. Y.; Pang, L. L.; Xue, W. J. Agric. Food Chem. 2005, 53, 7886. doi: 10.1021/jf051050w
8. [8]
  Liu, Y. X.; Cao, B. L.; Li, Y. H.; Song, H. B.; Huang, R. Q.; Wang, Q. M. J. Agric. Food Chem. 2007, 55, 3011. doi: 10.1021/jf0636519
9. [9]
  Zhao, Q. Q.; Liu, S. H.; Li, Y. H.; Wang, Q. M. J. Agric. Food Chem. 2009, 57, 2849. doi: 10.1021/jf803632t
10. [10]
  Ouyang, G. P.; Cai, X. J.; Chen, Z.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y.; Zeng, S. J. Agric. Food Chem. 2008, 56, 10160. doi: 10.1021/jf802489e
11. [11]
  Dai, H.; Liu, J. B.; Miao, W. K.; Wu, S. S.; Qin, X.; Zhang, X.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2011, 31, 1662 (in Chinese).
12. [12]
  Dai, H.; Shi, L.; Zhang, H. J.; Li, Y. Q.; Fang, J. X.; Shi, Y. J. Chin. J. Org. Chem. 2012, 32, 1060 (in Chinese). doi: 10.6023/cjoc1201292
13. [13]
  Wang, X.; Wang, C. Q.; Fu, C. R.; Zou, X. M. Chin. J. Org. Chem. 2015, 35, 92 (in Chinese). doi: 10.6023/cjoc201408017
14. [14]
  Dai, H.; Zhuang. H. Y.; Shi, L.; Li, G.; Zhang, H. J.; Fang, Y.; Dai, B. J. Chin. J. Org. Chem. 2015, 35, 2399 (in Chinese). doi: 10.6023/cjoc201506004
15. [15]
  Mu, C.-W.; Qin, Z.-H. Modern Agrochem. 2003, 2, 1 (in Chinese).
16. [16]
  Lahm, G. P.; Selby, T. P.; Freudenberger, J. H.; Stevenson, T. M.; Myers, B. J.; Seburyamo, G.; Simth, B. K.; Flexner, L.; Clark, C. E.; Cordova, D. Bioorg. Med. Chem. Lett. 2005, 15, 4898. doi: 10.1016/j.bmcl.2005.08.034
17. [17]
  Tian, Z. Z.; Shao, X. S.; Li, Z.; Qian, X. H.; Huang, Q. C. J. Agric. Food Chem. 2007, 55, 2288. doi: 10.1021/jf063418a
18. [18]
  Lu, S. Y.; Shao, X. S.; Li, Z.; Xu, Z. P.; Zhao, S. S.; Wu, Y. L.; Xu, X. Y. J. Agric. Food Chem. 2012, 60, 322. doi: 10.1021/jf203068a
19. [19]
  Selby, T. P.; Lahm, G. P.; Stevenson, T. M.; Hughes, K. A.; Cordova, D.; Annan, I. B.; Barry, J. D.; Benner, E. A.; Currie, M. J.; Pahutski, T. F. Bioorg. Med. Chem. Lett. 2013, 23, 6341. doi: 10.1016/j.bmcl.2013.09.076
20. [20]
  Wang, Q. M.; Sun, H. K.; Cao, H. Y.; Cheng, M. R.; Huang, R. Q. J. Agric. Food Chem. 2003, 51, 5030. doi: 10.1021/jf034067s
21. [21]
  Shi, Y. J.; Li, Y.; Fang, Y.; Chen, J.; Ye, L. Y.; Ge, S. S.; Dai, H. Chin. J. Org. Chem. 2016, 36, 2472 (in Chinese). doi: 10.6023/cjoc201605029
1. [1]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
2. [2]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
3. [3]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
4. [4]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
5. [5]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
6. [6]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
7. [7]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
8. [8]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
9. [9]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
10. [10]
  Hongjie SHEN , Haozhe MIAO , Yuhe YANG , Yinghua LI , Deguang HUANG , Xiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009
11. [11]
  Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073
12. [12]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
13. [13]
  Qiaowen CHANG , Ke ZHANG , Guangying HUANG , Nuonan LI , Weiping LIU , Fuquan BAI , Caixian YAN , Yangyang FENG , Chuan ZUO . Syntheses, structures, and photo-physical properties of iridium phosphorescent complexes with phenylpyridine derivatives bearing different substituting groups. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 235-244. doi: 10.11862/CJIC.20240311
14. [14]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
15. [15]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
16. [16]
  Zijian Zhao , Yanxin Shi , Shicheng Li , Wenhong Ruan , Fang Zhu , Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094
17. [17]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
18. [18]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
19. [19]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
20. [20]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(1409)
HTML views(157)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142