Citation: Zhu Yue, Zheng Dandan, Miao Heyi, Qian Cheng, Dai Hong, Liang Kai, Zhou Beibei, Shi Yujun, Xun Xiao, Wang Yang. Synthesis and Biological Activities of Novel Pyrazole Oxime Derivatives Containing Benzotriazolyl Moiety[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4315-4321. doi: 10.6023/cjoc202008031 shu

Synthesis and Biological Activities of Novel Pyrazole Oxime Derivatives Containing Benzotriazolyl Moiety

College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019

Corresponding author: Dai Hong, daihong_2015@aliyun.com Wang Yang, wangyang1617@sina.com
Received Date: 18 August 2020
Revised Date: 27 September 2020
Available Online: 13 October 2020
Fund Project: the National Natural Science Foundation of China 21372135the Science and Technology Project Fund of Nantong City MS12019060Project supported by the National Natural Science Foundation of China (Nos. 21372135, 21802075), and the Science and Technology Project Fund of Nantong City (No. MS12019060)the National Natural Science Foundation of China 21802075

Figures(3)

In search of new N-heterocyclic compounds possessing good biological activities, 17 novel pyrazole oxime derivatives were designed and synthesized by introducing benzotriazole moiety into pyrazole oxime skeleton based on fenpyroximate. Their structures were tested by ¹H NMR, ¹³C NMR and elemental analysis. Preliminary bioassay data displayed that 3 compounds showed 70%~100% insecticidal activities towards Tetranychus cinnabarinus at 20 μg/mL. 6 compounds possessed 90%~100% mortality rates towards Aphis medicaginis at 20 μg/mL. Moreover, 16 compounds displayed more than 80% insecticidal activities against Mythimna separata (Walker) at 500 μg/mL.
- benzotriazole,
- pyrazole oxime,
- synthesis,
- biological activity
1. [1]
  Wang, X.; Li, P.; Li, Z. N.; Yin, J.; He, M.; Xue, W.; Chen, Z. W.; Song, B. A. J. Agric. Food Chem. 2013, 61, 9575. doi: 10.1021/jf403193q
2. [2]
  Liu, Y. X.; Song, H. J.; Huang, Y. Q.; Li, J. R.; Zhao, S.; Song, Y. C.; Yang, P. W.; Xiao, Z. X.; Liu, Y. X.; Li, Y. Q.; Shang, H.; Wang, Q. M. J. Agric. Food Chem. 2014, 62, 9987. doi: 10.1021/jf503794g
3. [3]
  Gan, X. H.; Hu, D. Y.; Li, P.; Wu, J.; Chen, X. W.; Xue, W. Song, B. A. Pest. Manage. Sci. 2016, 72, 534. doi: 10.1002/ps.4018
4. [4]
  Kumar, K. S.; Ramulu, M. S.; Rajesham, B.; Kumar, N. P.; Voora, V.; Kancha, R. K. Org. Biomol. Chem. 2017, 15, 4468. doi: 10.1039/C7OB00715A
5. [5]
  Li, P.; Hu, D. Y.; Xie, D. D.; Chen, J. X.; Jin, L. H.; Song, B. A. J. Agric. Food Chem. 2018, 66, 3093. doi: 10.1021/acs.jafc.7b06061
6. [6]
  Yuan, Y.; Subedi, L.; Lim, D.; Jung, J. K.; Kim, S. Y.; Seo, S. Y. Bioorg. Med. Chem. Lett. 2019, 29, 329. doi: 10.1016/j.bmcl.2018.11.014
7. [7]
  Facchetti, G.; Rimoldi, I. Bioorg. Med. Chem. Lett. 2019, 29, 1257. doi: 10.1016/j.bmcl.2019.03.045
8. [8]
  Zhu, X. L.; Zhang, R.; Wu, Q. Y.; Song, Y. J.; Wang, Y. X.; Yang, J. F.; Yang, G. F. J. Agric. Food Chem. 2019, 67, 2774. doi: 10.1021/acs.jafc.8b06195
9. [9]
  Prandi, C.; Occhiato, E. G. Pest. Manage. Sci. 2019, 75, 2385. doi: 10.1002/ps.5322
10. [10]
  Zeng, D.; Wang, M. W.; Xiang, M.; Liu, L. W.; Wang, P. Y.; Li, Z.; Yang, S. Pest. Manage. Sci. 2020, 76, 2681. doi: 10.1002/ps.5814
11. [11]
  He, F. Q.; Wang, B. L.; Li, Z. M.; Song, H. B. Chin. J. Struct. Chem. 2006, 25, 543.
12. [12]
  Zhang, S. S.; Wan, J.; Li, X. M.; Li, C. L.; Xu, L. Z. Chem. Res. Chin. Univ. 2007, 23, 120. doi: 10.1016/S1005-9040(07)60024-5
13. [13]
  Fu, J.; Yang, Y.; Zhang, X. W.; Mao, W. J.; Zhang, Z. M.; Zhu, H. L. Bioorg. Med. Chem. 2010, 18, 8457. doi: 10.1016/j.bmc.2010.10.049
14. [14]
  Wan, J.; Lü, P. C.; Tian, N. N.; Zhu, H. L. J. Chem. Sci. 2010, 122, 597. doi: 10.1007/s12039-010-0094-8
15. [15]
  Mansour, A. M.; Mohamed, M. F. Inorg. Chim. Acta 2014, 423, 373. doi: 10.1016/j.ica.2014.08.034
16. [16]
  He, Z.; Zhang, S. F.; Xue, J. R.; Liang, Y.; Zhang, X.; Jin, L. H.; Qin, D. B. J. Organomet. Chem. 2016, 808, 12. doi: 10.1016/j.jorganchem.2016.02.005
17. [17]
  Wan, J.; Yan, X.; Ma, C. P.; Bi, S.; Zhu, H. L. Med. Chem. Res. 2010, 19, 970. doi: 10.1007/s00044-009-9243-3
18. [18]
  He, F. Q.; Liu, X. H.; Wang, B. L.; Li, Z. M. J. Chem. Res. 2006, 12, 809.
19. [19]
  Ouyang, G. P.; Chen, Z.; Cai, X. J.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y.; Zeng, S. Bioorg. Med. Chem. 2008, 16, 9699. doi: 10.1016/j.bmc.2008.09.070
20. [20]
  Dai, H.; Ye, L. Y.; Zhuang, H. Y.; Dai, B. J.; Fang, Y.; Shi, Y. J. Molecules 2015, 20, 21870. doi: 10.3390/molecules201219811
21. [21]
  Dai, H.; Yao, W.; Sun, S. Y.; Li, L.; Shi, L.; Qian, H. W.; Li, C. J.; Shi, J.; Shi, Y. J. Chin. J. Org. Chem. 2017, 37, 3155(in Chinese).
22. [22]
  Xiong, B.; Chen, S.; Zhu, P.; Huang, M. L.; Gao, W. J.; Zhu, R.; Qian, J. Q.; Peng, Y. F.; Zhang, Y. A.; Dai, H.; Ling, Y. Med. Chem. 2019, 15, 743. doi: 10.2174/1573406414666180827112724
23. [23]
  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
24. [24]
  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.3672
25. [25]
  Zhou, Q.; Zheng, D. D.; Shi, Y. J.; Yao, W.; Qian, H. W.; Ding, Y.; Wei, Z. H.; Shen, A. B.; Feng, X.; Shi, J.; Dai, H. Chin. J. Org. Chem. 2018, 38, 3318(in Chinese).
26. [26]
  Wang, Y.; Ye, H.; Qian, C.; Yao, W.; Li, H.; Wang, K.; Hu, L. P.; Li, L.; Wu, J. M.; Dai, H. Chin. J. Org. Chem. 2020, 40, 232(in Chinese).
27. [27]
  Dai, H.; Yao, W.; Fang, Y.; Sun, S. Y.; Shi, Y. J.; Chen, J.; Jiang, G. Q.; Shi, J. Molecules 2017, 22, 2000. doi: 10.3390/molecules22122000
28. [28]
  Wang, Y.; Ye, H.; Qian, C.; Yao, W.; Li, H.; Wang, K.; Hu, L. P.; Li, L.; Wu, J. M.; Dai, H. Chin. J. Org. Chem. 2020, 40, 528(in Chinese).
29. [29]
  Tanaka, A.; Terasawa, T.; Hagihara, H.; Sakuma, Y.; Ishibe, N.; Sawada, M.; Takasugi, H.; Tanaka, H. J. Med. Chem. 1998, 41, 2390. doi: 10.1021/jm9800853
30. [30]
  Dai, H.; Huang, M. L.; Qian, J. Q.; Liu, J.; Meng, C.; Li, Y. Y.; Ming, G. X.; Zhang, T.; Wang, S. L.; Shi, Y. J.; Yao, Y.; Ge, S. S.; Zhang, Y. A.; Ling, Y. Eur. J. Med. Chem. 2019, 166, 470. doi: 10.1016/j.ejmech.2019.01.070
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
9. [9]
  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
10. [10]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
11. [11]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
12. [12]
  Jian Jin , Jing Cheng , Xueping Yang . Integration Practice of Organic Chemistry Experiment and Safety Education: Taking the Synthesis of Triphenylmethanol as an Example. University Chemistry, 2024, 39(3): 345-350. doi: 10.3866/PKU.DXHX202309010
13. [13]
  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
14. [14]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
15. [15]
  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
16. [16]
  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
17. [17]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
18. [18]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
19. [19]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
20. [20]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006

Get Citation

PDF

XML

Metrics

PDF Downloads(51)
Abstract views(2977)
HTML views(369)

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