Citation: Xu Zhihong, Zhang Tao, Wang Shaokang, Li Junkai. Synthesis and Herbicidal Activities of Novel Ethyl 2-(4-(Pyridin-2-yl-oxy) phenyl-amino) propanoates/acetates[J]. Chinese Journal of Organic Chemistry, ;2017, 37(2): 526-532. doi: 10.6023/cjoc201608018 shu

Synthesis and Herbicidal Activities of Novel Ethyl 2-(4-(Pyridin-2-yl-oxy) phenyl-amino) propanoates/acetates

Xu Zhihong ^a ,
Zhang Tao ^b ,
Wang Shaokang ^b ,
Li Junkai ^a,*,,

a.
Hubei Collaborative Innovation Center for Grain Industry, Yangtze University, Jingzhou 434205
b.
Agricutural College, Yangtze University, Jingzhou 434205

Corresponding author: Li Junkai, junkaili@sina.com
Received Date: 23 August 2016
Revised Date: 6 September 2016

Figures(5)

Aryloxyphenoxypropionates (APPs) are a class of herbicides targeting on acetyl-coenzyme A carboxylase (ACCase) in monocot chloroplast. The article presents synthesis of twenty three novel ethyl 2-(4-(pyridin-2-yl-oxy) phenylamino)-propanoates/acetates, and their structures were characterized by ¹H NMR, HRMS and X-ray single-crystal diffraction. The herbicidal activities on barnyard grass and rape of the novel compounds were evaluated. Ethyl 2-(4-(5-nitropyridin-2-yloxy)-phenylamino) propanoate (B5) showed almost the same level of herbicidal activity on barnyard grass as commercial herbicide fluazifop-methyl which could become a potential lead compound on weeds.
- ethyl 2-(4-(pyridin-2-yl-oxy) phenylamino) propanoate/acetates,
- synthesis,
- herbicidal activity,
- acetyl-CoA carboxylase
1. [1]
  Burton, J. D.; Gronwald, J. W.; Somers, D. A.; Connelly, J. A.; Gengenbach, B. G.; Wyse, D. L. Biochem. Biophys. Res. Commun. 1987, 148, 1039. doi: 10.1016/S0006-291X(87)80236-X
2. [2]
  Lichthenthaler, K.; Kobek, H. K.; Ishii, K. Z. Naturforsch. 1987, 42c, 1275.
3. [3]
  Delye, C.; Zhang, X. Q.; Michel, S.; Matejicek, A.; Powles, S. B. Plant Physiol. 2005, 137, 794. doi: 10.1104/pp.104.046144
4. [4]
  Gronward, J. W. Weed Sci. 1991, 39, 435.
5. [5]
  Singh, G.; Singh, M.; Singh, V. P. Indian J. Weed Sci. 2002, 34, 165.
6. [6]
  Tietze, L. F. Chem. Rev. 1996, 96, 115. doi: 10.1021/cr950027e
7. [7]
  Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 21, 4101.
8. [8]
  Plowman, R. E.; Stonebridge, W. C.; Hawtree, J. N. Proceedings 1980 British Crop Protection Conference-Weeds, Brighton, England, 1980, p. 29.
9. [9]
  Menendez, J. C. Synthesis 2006, 2624.
10. [10]
  Ray, P. G.; Pews, R. G.; Flake, J. Proceedings 14th Conference Asian-Pacific Weed Science Society, Brisbane, Australia, 1993, p. 41.
11. [11]
  Dae, W. K.; Hae S. C.; Young, K. K.; Jae, W. R.; Jae, C. W.; Dong, W. K.; Jin, S. K. US 20030096706, 2003 [Chem. Abstr. 2003, 138, 364189].
12. [12]
  Coret, J. M. US 20050282706, 2005 [Chem. Abstr. 2005, 144, 33127].
13. [13]
  Graham, J. B.; Lindsay, E. C.; Graeme, J. F.; Wendy, A. J.; Jack, L.; Alexander, S.; Richard, B. W.; Keith, G. W. Bioorg. Med. Chem. Lett. 1997, 12, 1489.
14. [14]
  Liu, H.; Wang, H. Q.; Liu, Z. J. Bioorg. Med. Chem. Lett. 2007, 17, 2203. doi: 10.1016/j.bmcl.2007.01.083
15. [15]
  Huang, T. H.; Tu, H. Y.; Zumureti, A.; Hou, C. J.; Zhang, A. D. ARKIVOR 2011, 2, 1.
16. [16]
  Zhu, Y.-Q.; Zou, X.-M.; Hu, F.-Z.; Yao, C.-S.; Liu, B.; Li, Y.-H.; Yang, H.-Z. J. Agric. Food Chem. 2005, 53, 9566. doi: 10.1021/jf051510l
17. [17]
  Zhu, Y. Q.; Wu, C.; Li, H. B.; Zou, X. M.; Si, X. K.; Hu, F. Z.; Yang, H. Z. J. Agric. Food Chem. 2007, 55, 1364. doi: 10.1021/jf063271n
18. [18]
  Han, J. T.; Dong, H. B.; Xu, Z. H.; Lei, J. P.; Wang, M. A. Int. J. Mol. Sci. 2013, 14, 12484. doi: 10.3390/ijms140612484
19. [19]
  Han, J. T.; Wang, J. M.; Dong, H. B.; Xu, Z. H.; Liu, B.; Wang, M. A. Chin. J. Org. Chem. 2013, 33, 596 (in Chinese). doi: 10.6023/cjoc201210046
20. [20]
  Han, J. T.; Dong, H. B.; Wang, J. M.; Lei, J. P.; Wang, M. A.; Fang, J. X. Molecules 2011, 16, 2833. doi: 10.3390/molecules16042833
21. [21]
  Xu, Z. H.; Wang, J. M.; Han, J. T.; Liu, B.; Wang, M. A. Chin. J. Org. Chem. 2012, 32, 2134 (in Chinese). doi: 10.6023/cjoc201206002
22. [22]
  Xu, Z. H.; Dong, H. B.; Liu, B.; Kong, L. Q.; Wang, M. A. Chin. J. Org. Chem. 2015, 35, 411 (in Chinese). doi: 10.6023/cjoc201409043
23. [23]
  Liu, B.; Dong, H. B.; Han, J. T.; Xu, Z. H.; Jin, S. H.; Wang, M. A. Chin. J. Org. Chem. 2013, 33, 2538 (in Chinese). doi: 10.6023/cjoc201307019
24. [24]
  Kluth, J.; Santel, H. J.; Schmidt, R. R. DE 3638151, 1987 [Chem. Abstr. 1988, 108, 111985].
25. [25]
  Wang, W.; He, H. W.; Zuo, N.; He, H. F.; Peng, H.; Tan, X. S. J. Agric. Food Chem. 2012, 60, 7581. doi: 10.1021/jf301829m
26. [26]
  He, H. W.; Chen, T.; Li, Y. J. J. Pestic. Sci. 2007, 32, 42. doi: 10.1584/jpestics.G06-05
27. [27]
  Peng, H.; Wang, T.; Xie, P.; Chen, T.; He, H. W.; Wan, J. J. Agric. Food Chem. 2007, 55, 1871. doi: 10.1021/jf062730h
28. [28]
  He, H. W.; Yuan, J. L.; Peng, H.; Chen, T.; Shen, P.; Wan, S. Q.; Li, Y. J.; Tan, H. L.; He, Y. H.; He, J. B.; Li, Y. J. Agric. Food Chem. 2011, 59, 4801. doi: 10.1021/jf104247w
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  Jiaojiao Yu , Bo Sun , Na Li , Cong Wen , Wei Li . Improvement of Classical Organic Experiment Based on the “Reverse-Step Optimization Method”: Taking Synthesis of Ethyl Acetate as an Example. University Chemistry, 2025, 40(3): 333-341. doi: 10.12461/PKU.DXHX202405177
5. [5]
  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
6. [6]
  Shuying Zhu , Shuting Wu , Ou Zheng . Improvement and Expansion of the Experiment for Determining the Rate Constant of the Saponification Reaction of Ethyl Acetate. University Chemistry, 2024, 39(4): 107-113. doi: 10.3866/PKU.DXHX202310117
7. [7]
  Ruitong Zhang , Zhiqiang Zeng , Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004
8. [8]
  Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
9. [9]
  Quanliang Chen , Zhaohui Zhou . Research on the Active Site of Nitrogenase over Fifty Years. University Chemistry, 2024, 39(7): 287-293. doi: 10.3866/PKU.DXHX202310133
10. [10]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
11. [11]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
12. [12]
  Li Jiang , Changzheng Chen , Yang Su , Hao Song , Yanmao Dong , Yan Yuan , Li Li . Electrochemical Synthesis of Polyaniline and Its Anticorrosive Application: Improvement and Innovative Design of the “Chemical Synthesis of Polyaniline” Experiment. University Chemistry, 2024, 39(3): 336-344. doi: 10.3866/PKU.DXHX202309002
13. [13]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
14. [14]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
15. [15]
  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
16. [16]
  Chunmei GUO , Weihan YIN , Jingyi SHI , Jianhang ZHAO , Ying CHEN , Quli FAN . Facile construction and peroxidase-like activity of single-atom platinum nanozyme. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1633-1639. doi: 10.11862/CJIC.20240162
17. [17]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
18. [18]
  Zhuoya WANG , Le HE , Zhiquan LIN , Yingxi WANG , Ling LI . Multifunctional nanozyme Prussian blue modified copper peroxide: Synthesis and photothermal enhanced catalytic therapy of self-provided hydrogen peroxide. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2445-2454. doi: 10.11862/CJIC.20240194
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(1183)
HTML views(147)

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