Citation: Dai Hong, Ye Linyu, Li Yang, Fang Yuan, Shi Yujun, Liang Zhipeng, Shi Jian. Synthesis and Biological Activities of Novel Pyrazole Oximes Containing Substituted Pyrimidine Group[J]. Chinese Journal of Organic Chemistry, ;2017, 37(4): 1020-1026. doi: 10.6023/cjoc201611042 shu

Synthesis and Biological Activities of Novel Pyrazole Oximes Containing Substituted Pyrimidine Group

Dai Hong ^a ,
Ye Linyu ^a ,
Li Yang ^b ,
Fang Yuan ^b ,
Shi Yujun ^a,b,*,, ,
Liang Zhipeng ^c ,
Shi Jian ^c,*,,

a.
College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019
b.
School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003
c.
Analysis and Testing Center, Nantong University, Nantong 226019

Corresponding author: Shi Yujun, yjshi2015@163.com Shi Jian, gaohbhe2015@aliyun.com
Received Date: 30 November 2016
Revised Date: 4 January 2017

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 Graduate Students of Nantong University YKC16086

Figures(3)

In order to explore novel potent pesticide from pyrazole oxime derivatives, a series of new pyrazole oxime compounds carrying substituted pyrimidine moiety were synthesized by the method of active substructure combination. The structures of the title compounds were characterized by ¹H NMR, ¹³C NMR, MS and elemental analysis. Preliminary bioassay data displayed that some target compounds showed certain insecticidal activities. At the concentration of 500 μg/mL, compounds 6b and 6c exhibited 60% and 70% insecticidal activity against Aphis craccivora, compounds 6a, 6b, 6c, and 6d had 100%, 100%, 100% and 90% insecticidal activity against Nilaparvata lugens. When the concentration was reduced to 100 μg/mL, compounds 6a, 6b and 6d were still active against Nilaparvata lugens with inhibitory values of 60%, 60% and 50%, respectively. In addition, insecticidal activities against Oriental armyworm of compounds 6f, 6g and 6m were 80%, 70% and 90%, respectively, at 500 μg/mL.
- pyrimidine,
- pyrazole oxime,
- synthesis,
- bioactivity
1. [1]
  Motoba, K.; Nishizawa, H.; Suzuki, T.; Hamaguchi, H.; Uchida, M.; Funayama, S. Pestic. Biochem. Physiol. 2000, 67, 73. doi: 10.1006/pest.2000.2477
2. [2]
  Li, Y.; Zhang, H. Q.; Liu, J.; Yang, X. P.; Liu, Z. J. J. Agric. Food Chem. 2006, 54, 3636. doi: 10.1021/jf060074f
3. [3]
  Dai, H.; Li, Y. Q.; Du, D.; Qin, X.; Zhang, X.; Yu, H. B.; Fang, J. X. J. Agric. Food Chem. 2008, 56, 10805. doi: 10.1021/jf802429x
4. [4]
  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).
5. [5]
  Dai, H.; Yu, H. B.; Liu, J. B.; Qin, X.; Wang, T. T.; Zhang, X.; Qin. Z. F.; Fang, J. X. Chin. J. Org. Chem. 2013, 33, 1104 (in Chinese).
6. [6]
  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
7. [7]
  Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173. doi: 10.1584/jpestics.20.173
8. [8]
  Swanson, M. B.; Ivancic, W. A.; Saxena, A. M.; Allton, J. D.; O'Brien, G. K.; Suzuki, T.; Nishizawa, H.; Nokata, M. J. Agric. Food Chem. 1995, 43, 513. doi: 10.1021/jf00050a048
9. [9]
  Fu, C. R.; Peng, J.; Ning, Y.; Liu, M.; Shan, P. C.; Liu, J.; Li, Y. Q.; Hu, F. Z.; Zhu, Y. Q.; Yang, H. Z.; Zou, X. M. Pest Manage. Sci. 2014, 70, 1207. doi: 10.1002/ps.2014.70.issue-8
10. [10]
  Wang, S. L.; Shi, Y. J.; He, H. B.; Li, Y.; Li, Y.; Dai, H. Chin. Chem. Lett. 2015, 26, 672. doi: 10.1016/j.cclet.2015.04.017
11. [11]
  Dai, H.; Ge, S. S.; Li, G.; Chen, J.; Shi, Y. J.; Ye, L. Y.; Ling, Y. Bioorg. Med. Chem. Lett. 2016, 26, 4504. doi: 10.1016/j.bmcl.2016.07.068
12. [12]
  Wei, Z. Z.; Peng, H. L.; Liu, A. P.; Cheng, H.; Ling, L. Z.; Liu, Y.; Hu, C. H.; Yang, G. F. Chin. J. Org. Chem. 2006, 26, 1120 (in Chinese). doi: 10.3321/j.issn:0253-2786.2006.08.018
13. [13]
  Zai, W. J.; Jiang, P. P.; Zhang, X. Y.; Loiseau, P. M.; Guo, S. H.; Fan, X. S. Chin. J. Org. Chem. 2015, 35, 1335 (in Chinese).
14. [14]
  Lü, Q.; Lu, X. T.; Dai, M.; Liu, S. M.; Zhu, W. H.; Du, P.; Lü, L. Chin. J. Org. Chem. 2015, 35, 1260 (in Chinese).
15. [15]
  Jiang, L. L.; Chen, C. N.; Zhou, Y. F.; Chen, Q.; Yang, G. F. Chin. J. Org. Chem. 2009, 29, 1392 (in Chinese).
16. [16]
  Yue, X. L.; Wei, X. Q.; Zheng, Q. Chin. J. Org. Chem. 2009, 29, 764 (in Chinese).
17. [17]
  Cheng, X.; Wang, S.; Cui, D.; Li, B. J. Heterocycl. Chem. 2014, 52, 607.
18. [18]
  Ma, H. J.; Zhang, J. H.; Xia, X. D.; Xu. M. H.; Ning, J.; Li, J. H. Pest Manage. Sci. 2014, 70, 946. doi: 10.1002/ps.2014.70.issue-6
19. [19]
  Zhang, L.; Lin, Y.; Wang, J.; Zhu, X. L.; Yao, Q. L.; Yao, Q. Z. Chin. J. Org. Chem. 2015, 35, 497 (in Chinese).
20. [20]
  Lü, Q.; Lu, X. T.; Zhang, J. S.; Zhang, Z. G.; Zhu, W. H.; Du, P.; Lü, L. Chin. J. Org. Chem. 2015, 35, 1342 (in Chinese).
21. [21]
  Dai, H.; Huang, J. H.; Jin, Z. C.; Cheng, X. Y.; Huang, K. W.; Ling, Y.; Wang, Q. M.; Shi, Y. J. Chin. J. Org. Chem. 2015, 35, 2617 (in Chinese).
22. [22]
  Dai, H.; Fang, Y.; Li, Y.; Wang, X. L.; Xiang, X. B.; Ge, S. S.; Shi, Y. J. Chin. J. Org. Chem. 2016, 36, 2973 (in Chinese).
23. [23]
  Dai, H.; Zhang, Y. T.; Shi, Y. J.; Zhang, W. W.; Shen, Y. J. Acta Crystallogr. 2011, E67, o727.
24. [24]
  Dai, H.; Miao, W. K.; Wu, S. S.; Qin, X.; Fang, J. X. Acta Crystallogr. 2011, E67, o775.
25. [25]
  Fan, C. G.; Chen, J. C.; Dai, H.; Wei, Y. H.; Shi, Y. J. Acta Crystallogr. 2012, E68, o3122.
26. [26]
  Liu, T. T.; Ni, Y.; Zhong, L. K.; Huang, H. Y.; Hu, W. Q.; Xu, T. M.; Tan, C. X. Chin. J. Org. Chem. 2015, 35, 422 (in Chinese).
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]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
4. [4]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
5. [5]
  Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
6. [6]
  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
7. [7]
  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
8. [8]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
9. [9]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
10. [10]
  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
11. [11]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
12. [12]
  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
13. [13]
  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
14. [14]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
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]
  Yihui Song , Shangshang Qin , Kai Wu , Chengyun Jin , Bin Yu . 生物化学在高水平创新型药学人才培养中的交叉融合应用——以去甲基化酶LSD1抑制剂的活性评价为例. University Chemistry, 2025, 40(6): 341-352. doi: 10.12461/PKU.DXHX202406018
17. [17]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
18. [18]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
19. [19]
  Qingying Gao , Tao Luo , Jianyuan Su , Chaofan Yu , Jiazhu Li , Bingfei Yan , Wenzuo Li , Zhen Zhang , Yi Liu . Refinement and Expansion of the Classic Cinnamic Acid Synthesis Experiment. University Chemistry, 2024, 39(5): 243-250. doi: 10.3866/PKU.DXHX202311074
20. [20]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(1191)
HTML views(134)

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