Citation: Ding Chengrong, Pan Yayun, Yin Xu, Tan Chengxia, Zhang Guofu. Synthesis and Insecticidal Activity of Novel Piperidine Thiazole Compounds[J]. Chinese Journal of Organic Chemistry, ;2019, 39(3): 836-841. doi: 10.6023/cjoc201809009 shu

Synthesis and Insecticidal Activity of Novel Piperidine Thiazole Compounds

College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310032

Corresponding author: Tan Chengxia, tanchengxia@zjut.edu.cn Zhang Guofu, gfzhang@zjut.edu.cn
Received Date: 5 September 2018
Revised Date: 22 October 2018
Available Online: 25 March 2018
Fund Project: Project supported by the Collaborative Innovation Center of Zhejiang Province Green Pesticide

Figures(2)

Twelve new piperdine thiazole compounds were designed and synthesized in search of new bioactive compounds. The preliminary bioassay showed that at the concentration of 500 μg/mL the lethal rates of the target compounds possessed certain insceticidal activities against armyworm, and at the concentration of 100 μg/mL the lethal rates of (4-(5-(3-chloro-phenyl) -4-methylthiazol-2-yl) piperidin-1-yl) (4-methylpiperazin-1-yl) methanone (1f) and (4-(5-(4-chlorophenyl) -4-methyl-thiazol-2-yl) piperidin-1-yl) nitro-1H-pyrazol-3-yl) methanone (1g) against armyworm were 80% and 100%, respectively. Further screening at concentrations of 20 μg/mL, the lethal rate of (4-(5-(4-chlorophenyl) -4-methylthiazol-2-yl) piperidin-1-yl) (4-nitro-1H-pyrazol-3-yl) methanone (1g) against armyworm was 50%.
- oxathiapiprolin,
- piperidine-thiazolederivatives,
- insecticidal activity
1. [1]
  Huang, G.; Yang, J.-C.; Li, H.-C. Agrochemicals 2011, 50, 79(in Chinese.
2. [2]
  Yang, Z.-H.; Tian, H.; Zhang, L. World Pestic. 2017, 39, 43(in Chinese).
3. [3]
  Tan, Y.; Zhang, B.-H. J. Math. Med. 2012, 25, 89(in Chinese).
4. [4]
  Biller, S. A. US 5739135, 1998[Chem. Abstr. 1998, 128, 282780].
5. [5]
  Guedat, P. US 20070054939, 2007[Chem. Abstr. 2007, 142, 93809].
6. [6]
  Li, Y. CN 106588911, 2017[Chem. Abstr. 2017, 166, 515724].
7. [7]
  Fan, Z. J. CN 104650060, 2015[Chem. Abstr. 2015, 163, 65937].
8. [8]
  Gu, L.-L.; Bai, Y.-L. Mod. Agrochem. 2017, 16, 42(in Chinese).
9. [9]
  He, X.-L. World Pestic. 2015, 37, 57(in Chinese).
10. [10]
  Cederbaum, F. WO 2014118142, 2014[Chem. Abstr. 2014, 161, 320959].
11. [11]
  Lamberth, C. WO 2014154530, 2014[Chem. Abstr. 2014, 161, 640429].
12. [12]
  Tomoki, T. US 20130296272, 2013[Chem. Abstr. 2012, 156, 337332].
13. [13]
  Gregory, V. WO 2009055514, 2009[Chem. Abstr. 2009, 150, 578441].
14. [14]
  Stefan, H. US 20160198713, 2016[Chem. Abstr. 2016, 162, 400022].
15. [15]
  Pierre, C. US 20110312999, 2011[Chem. Abstr. 2011, 155, 615369].
16. [16]
  Hanagan, M. A. WO 2009094407, 2009[Chem. Abstr. 2009, 151, 234956].
17. [17]
  Kamireddy, B. WO 2009094445, 2009[Chem. Abstr. 2009, 151, 173451].
18. [18]
  Pasteris, R. J. WO 2008013925, 2008[Chem. Abstr. 2008, 148, 185163].
19. [19]
  Yi, A.-Q.; Xue, S.-J.; Fang, Z.-K. Chin. J. Org. Chem. 2009, 29, 454(in Chinese).
20. [20]
  Hong, Y.; Dai, H.; Ye, Y.-L. Chin. J. Org. Chem. 2017, 37, 3006(in Chinese).
21. [21]
  Gao, H.; Zheng, X.; Zhu, P. Chin. J. Org. Chem. 2018, 38, 684(in Chinese).
22. [22]
  Zhang, Z.-H.; Chen, Y.; Cai, B.-S. Chin. J. Org. Chem. 2017, 37, 2377(in Chinese).
23. [23]
  Cao, L.; Sun, J.-W.; Liu, Q. Chin. J. Org. Chem. 2017, 37, 3031(in Chinese).
24. [24]
  Ma, H.-L.; Yan, X.-J.; Xiao, Y.-M. Chin. J. Org. Chem. 2016, 36, 158(in Chinese).
25. [25]
  Sun, N.; Wang, X.; Ding, Z.-B. Chin. J. Org. Chem. 2016, 36, 2489(in Chinese).
26. [26]
  Li, R.; Nakashima, T.; Galangau, O. Chem. Asian J. 2015, 10, 1725. doi: 10.1002/asia.v10.8
27. [27]
  Khillare, L. D.; Pratap, U. R.; Bhosle, M. R. Chem. Intermed. 2017, 12, 1.
28. [28]
  Tong, D.; Duan, H.; Wang, J. Chem. Res. Chin. Univ. 2014, 30, 4. doi: 10.1007/s40242-014-3467-6
29. [29]
  Hantzsch, A.; Weber, J. H. Chem. Ber. 1887, 20, 3118. doi: 10.1002/(ISSN)1099-0682
30. [30]
  Parsons P. J.; Johnathan. B.; Waters A. J. Synth. Commun. 2007, 37, 985. doi: 10.1080/00397910601163950
31. [31]
  Srivatsavati, Jagapathi, R.; Pothukuchi, S.; Rani, S.-S. WO 2012143933, 2012[Chem. Abstr. 2012, 167, 481902].
32. [32]
  Dai, H.; Ye, L. Y.; Zhuang, H. Y.; Dai, B. J.; Fang, Y.; Shi, Y. J. Molecules 2015, 20, 21870. doi: 10.3390/molecules201219811
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