Citation: Liang Kai, Zhou Qian, Xun Xiao, Ni Yadan, Li Jinfeng, Shi Yujun, Zhou Huanyu, Wu Xinxing, Shi Jian, Gao Lei, Dai Hong. Synthesis and Insecticidal Activities of Novel Pyrazole Amide Derivatives Containing a Thiazole Unit[J]. Chinese Journal of Organic Chemistry, ;2020, 40(6): 1665-1672. doi: 10.6023/cjoc202001029 shu

Synthesis and Insecticidal Activities of Novel Pyrazole Amide Derivatives Containing a Thiazole Unit

Liang Kai ^a,† ,
Zhou Qian ^a,† ,
Xun Xiao ^a ,
Ni Yadan ^a ,
Li Jinfeng ^a ,
Shi Yujun ^a,, ,
Zhou Huanyu ^a ,
Wu Xinxing ^a,, ,
Shi Jian ^b ,
Gao Lei ^a ,
Dai Hong ^a,,

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

Corresponding author: Shi Yujun, yjshi2015@163.com Wu Xinxing, wuxinxng@163.com Dai Hong, daihong_2015@aliyun.com

^†

Received Date: 22 January 2020
Revised Date: 25 February 2020
Available Online: 29 February 2020
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21372135), the Science and Technology Project Fund of Nantong City (No. MS12019060) and the Program of High-level Talents of Nantong University (No. 03083031)the Science and Technology Project Fund of Nantong City MS12019060the National Natural Science Foundation of China 21372135the Program of High-level Talents of Nantong University 03083031

Figures(3)

In search of novel pyrazole amide compounds possessing good biological activities, a series of pyrazole amides were synthesized by introducing thiazole unit into pyrazole ring via amido bond, based on the lead of tebufenpyrad. The title compounds were structurually confirmed by ¹H NMR, ¹³C NMR and elemental analysis. Preliminary bioassay displayed that all the title compounds exhibited 100% insecticidal activities against Oriental armyworm at 500 μg/mL. At the concentration of 500 μg/mL, seven compounds showed 70%~100% mortality rate against Aphis medicaginis. In addition, three compounds had 40%~50% insecticidal activity against Tetranychus cinnabarinus at 500 μg/mL.
- thiazole,
- pyrazole amide,
- synthesis,
- insecticidal activity
1. [1]
  Prakash, T. B.; Reddy, G. D.; Padmaja, A.; Padmavathi, V. Eur. J. Med. Chem. 2014, 82, 347. doi: 10.1016/j.ejmech.2014.06.001
2. [2]
  Guan, A. Y.; Qin, Y. K.; Wang, J. F.; Li, B. J. Fluorine Chem. 2013, 156, 120. doi: 10.1016/j.jfluchem.2013.09.003
3. [3]
  Li, G. Y.; Qian, X. H.; Cui, J. N.; Huang, Q. C.; Zhang, R.; Guan, H. J. Agric. Food Chem. 2006, 54, 125. doi: 10.1021/jf051928j
4. [4]
  Ohnmacht, S. A.; Ciancimino, C.; Vignaroli, G.; Gunaratnam, M.; Neidle, S. Bioorg. Med. Chem. Lett. 2013, 23, 5351. doi: 10.1016/j.bmcl.2013.07.057
5. [5]
  Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Yuan, J.; Yang, G.; Xu, T. M.; Peng, W. L. Bioorg. Med. Chem. Lett. 2016, 26, 3626. doi: 10.1016/j.bmcl.2016.06.004
6. [6]
  Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L. Eur. J. Med. Chem. 2017, 125, 881. doi: 10.1016/j.ejmech.2016.10.017
7. [7]
  Shi, J. J.; Ren, G. H.; Wu, N. J.; Weng, J. Q.; Xu, T. M.; Liu, X. H.; Tan, C. X. Chin. Chem. Lett. 2017, 28, 1727. doi: 10.1016/j.cclet.2017.05.015
8. [8]
  Wang, B. L.; Zhu, H. W.; Li, Z. M.; Wang, L. Z.; Zhang, X.; Xiong, L. X.; Song, H. B. Pest Manage. Sci. 2018, 74, 726. doi: 10.1002/ps.4770
9. [9]
  Yu, H. B.; Qin, Z. F.; Dai, H.; Zhang, X.; Qin, X.; Wang, T. T.; Fang, J. X. J. Agric. Food Chem. 2008, 56, 11356. doi: 10.1021/jf802802g
10. [10]
  Wang, H. L.; Ruan, L. L.; Chen, Y.; Liu, X. H.; Weng, J. Q. Chin. J. Org. Chem. 2015, 34, 419 (in Chinese).
11. [11]
  Pember, S. O.; Mejia, G. L.; Price, T. J.; Pasteris, R. J. Bioorg. Med. Chem. Lett. 2016, 26, 2965. doi: 10.1016/j.bmcl.2016.02.061
12. [12]
  Mabkhot, Y. N.; Alharbi, M. M.; Al-Showiman, S. S.; Ghabbour, H. A.; Kheder, H. A.; Soliman, S. M.; Frey, W. Chem. Cent. J. 2018, 12, 56. doi: 10.1186/s13065-018-0420-7
13. [13]
  Althagafi, I.; El-Metwaly, N.; Farahaly, T. A. Molecules 2019, 24, 1741. doi: 10.3390/molecules24091741
14. [14]
  Maienfisch, P. L.; Huerlimann, H.; Rindlisbacher, A.; Gsell, L.; Dettwiler, H.; Haettenschwiler, J.; Sieger, E.; Walti, M. Pest Manage. Sci. 2001, 57, 165. doi: 10.1002/1526-4998(200102)57:2<165::AID-PS289>3.0.CO;2-G
15. [15]
  Cao, S. W.; Liu, A. P.; Liu, W. D.; Liu, X. P.; Ren, Y. G.; Pei, H.; Huang, L.; Zheng, X.; Huang, M. Z.; Wu, D. X. J. Heterocycl. Chem. 2017, 54, 3395. doi: 10.1002/jhet.2961
16. [16]
  Ding, C. R.; Pan, Y. Y.; Yin, X.; Tan, C. X.; Zhang, G. F. Chin. J. Org. Chem. 2019, 39, 836 (in Chinese).
17. [17]
  Ding, C. R.; Pan, Y. Y.; Yin, X.; Tan, C. X. Chin. J. Org. Chem. 2019, 39, 2099 (in Chinese).
18. [18]
  Dai, H.; Li, G.; Chen, J.; Shi, Y. J.; Ge, S. S.; Fan, C. G.; He, H. B. Bioorg. Med. Chem. Lett. 2016, 26, 3818. doi: 10.1016/j.bmcl.2016.04.094
19. [19]
  Dai, H.; Chen, J.; Li, G.; Ge, S. S.; Shi, Y. J.; Fang, Y.; Ling, Y. Bioorg. Med. Chem. Lett. 2017, 27, 950. doi: 10.1016/j.bmcl.2016.12.083
20. [20]
  Monicka, J. C.; James, C. J. Mol. Struct. 2014, 1075, 335. doi: 10.1016/j.molstruc.2014.07.002
21. [21]
  Fulcher, J. M.; Wayment, D. G.; White, Jr, P. M.; Webber Ⅲ, C. L.; J. Agric. Food Chem. 2014, 62, 2141. doi: 10.1021/jf405506p
22. [22]
  Dai, H.; Ge, S. S.; Guo, J.; Chen, S.; Huang, M. L.; Yang. J. Y.; Sun, S. Y.; Ling, Y.; Shi, Y. J. Eur. J. Med. Chem. 2018, 143, 1066. doi: 10.1016/j.ejmech.2017.11.098
23. [23]
  Gu, B. Q.; Zhu, W. Q.; Fan, W. Z.; Qian, H.; Liu, J. M.; Zhang, A. Q.; Shen, R. X. Modern Agrochem. 2002, 1, 9 (in Chinese).
24. [24]
  Fan, W. Z.; Gu, B. Q.; Zhu, W. Q.; Zhang, Y. B. Modern Agrochem. 2005, 4, 9 (in Chinese). doi: 10.3969/j.issn.1671-5284.2005.02.002
25. [25]
  Hughes, K. A.; Lahm, G. P.; Selby, T. P.; Stevenson, T. M. WO 2004067528, 2004[Chem. Abstr. 2004, 141, 190786].
26. [26]
  Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173. doi: 10.1584/jpestics.20.173
27. [27]
  Yang, Z. B.; Hu, D. Y.; Zeng, S.; Song, B. A. Bioorg. Med. Chem. Lett. 2016, 26, 1161. doi: 10.1016/j.bmcl.2016.01.047
28. [28]
  Zhao, W.; Shen, Z. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. J. Heterocycl. Chem. 2017, 54, 1751. doi: 10.1002/jhet.2753
29. [29]
  Cheng, L.; Shen, Z. H.; Xu, T. M.; Tan, C. X.; Weng, J. Q.; Han, L.; Peng, W. L.; Liu, X. H. J. Heterocycl. Chem. 2018, 55, 946. doi: 10.1002/jhet.3123
30. [30]
  Lima, L. M. A.; Barreiro, E. J. Curr. Med. Chem. 2005, 12, 23. doi: 10.2174/0929867053363540
31. [31]
  Romagnoli, R.; Baraldi, P. G.; Salvador, M. K.; Preti, D.; Tabrizi, M. A.; Brancale, A.; Fu, X. H.; Li, J.; Zhang, S. Z.; Hamel, E.; Bortolozzi, R.; Basso, G.; Viola, G. J. Med. Chem. 2012, 55, 475.
32. [32]
  Wang, Q. M.; Li, H.; Li, Y. H.; Huang, R. Q. J. Agric. Food Chem. 2004, 52, 1918. doi: 10.1021/jf035312a
33. [33]
  Liu, Y. X.; Wei, D. G.; Zhu, Y. R.; Liu, S. H.; Zhang, Y. L.; Zhao, Q. Q.; Cai, B. L.; Li, Y. H.; Song, H. B.; Liu, Y.; Wang, Y.; Huang, R. Q.; Wang, Q. M. J. Agric. Food Chem. 2008, 56, 204. doi: 10.1021/jf072851x
34. [34]
  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
35. [35]
  Yang, Y. Z.; Lin, D. Y.; Fu, C. R.; Zou, X. M. Chin. J. Org. Chem. 2015, 35, 100 (in Chinese).
36. [36]
  Wang, B. L.; Zhu, H. W.; Ma, Y.; Xiong, L. X.; Li, Y. Q.; Zhao, Y.; Zhang, J. F.; Chen, Y. W.; Zhou, S.; Li, Z. M. J. Agric. Food Chem. 2013, 61, 5483. doi: 10.1021/jf4012467
37. [37]
  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
38. [38]
  Shi, Y. J.; Ye, L. Y.; Zhong, S. L.; Cao, X. F.; Dai, H.; Hong, Y.; Li, C. J.; Shi, J.; Wu, J. M. Chin. J. Org. Chem. 2017, 37, 1844 (in Chinese).
39. [39]
  Shao, L.; Zhou, X.; Zhang, Q.; Liu, J. B.; Jin, Z.; Fang, J. X. Synth. Commun. 2007, 37, 199. doi: 10.1080/00397910601031629
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]
  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
4. [4]
  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
5. [5]
  Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007
6. [6]
  Ying Chen , Ronghua Yan , Weiyan Yin . Research Progress on the Synthesis of Metal Single-Atom Catalysts and Their Applications in Electrocatalytic Hydrogen Evolution Reactions. University Chemistry, 2025, 40(9): 344-353. doi: 10.12461/PKU.DXHX202503066
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076
14. [14]
  Xinghai Li , Zhisen Wu , Lijing Zhang , Shengyang Tao . Machine Learning Enables the Prediction of Amide Bond Synthesis Based on Small Datasets. Acta Physico-Chimica Sinica, 2025, 41(2): 2309041-0. doi: 10.3866/PKU.WHXB202309041
15. [15]
  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
16. [16]
  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
17. [17]
  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
18. [18]
  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
19. [19]
  Junyuan Zhang , Zhiwei Miao . 有机磷杀虫剂的前世今生. University Chemistry, 2025, 40(6): 129-138. doi: 10.12461/PKU.DXHX202408118
20. [20]
  Yingpeng ZHANG , Xingxing LI , Yunshang YANG , Zhidong TENG . A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064

Get Citation

PDF

XML

Metrics

PDF Downloads(15)
Abstract views(1352)
HTML views(242)

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