Shunhong CHEN, Feng HE, Yu ZHANG, Dexia LUO, Jian WU, Gang YU

Synthesis and bioactivity of sulfide derivatives containing 1,3,4-oxadiazole and pyridine

A series of novel sulfide derivatives containing 1,3,4-oxadiazole and pyridine were synthesized, characterized,and tested for their antibacterial activity against tobacco bacterial wilt and rice bacterial blight and for insecticidalactivity toward diamondback moth. The results showed that some compounds had good insecticidal and bactericidal activity, e.g., the activities of compounds 6e and 6g–6j toward tobacco bacterial wilt were much better than those of commercial thiodiazole-copper, and some of the synthesized compounds possessed good insecticidal activity against Plutella xylostella. Compounds 6d, 6h, 6j, 6l, 6p, 6r, and 6p displayed over 93% activity at 500 mg L −1.

PDF

___

1. Zou, L. F.; Li, Y. R.; Chen, G. Y. Agric. Sci. China 2011, 10, 1139-1150.
2. Kang, M. J.; Shim, J. K.; Cho, M. S.; Seol, Y. J.; Hahn, J. H.; Hwang, D. J.; Park, D. S. J. Microbiol. Biotechnol. 2008, 18, 1492-1495.
3. Shetty, N. S.; Khazi, I. A. M.; Ahn, C. B. Kor. Chem. Soc. 2010, 31, 2337-2340.
4. Zhang, L.; Qi, Q.; Yang, J.; Sun, D.; Li, C.; Xue, Y.; Jiang, Q.; Tian, Y.; Xu, C.; Wang, R. Oxid. Med. Cell. Longev. 2015, 6, 1-8.
5. Hou, L.; Shan, X.; Hao, L.; Feng, Q.; Zhang, Z. Acta Biomater. 2017, 54, 307-320.
6. Brigg, S.; Pribut, N.; Basson, A. E.; Avgenikos, M.; Venter, R.; Blackie, M. A.; van Otterlo, W. A. L.; Pelly, S. C. Bioorg. Med. Chem. Lett. 2016, 26, 1580-1584.
7. Xu, F. Z.; Shao, J. H.; Zhu, Y. Y.; Liu, L. W.; Zhao, Y. H.; Shan, W. L.; Wang, Y. Y.; Wu, J.; Yang, S.; Xue, W. Chem. Pap. 2017, 71, 729-739.
8. Wu, J.; Bai, S.; Yue, M.; Luo, L. J.; Shi, Q. C.; Ma, J.; Du, X. L.; Kang, S. H.; Hu, D. Y.; Yang, S. Chem. Pap. 2014, 68, 969-975.
9. Deng, S. L.; Chen, R. Y. Synthesis 2002, 17, 2527-2531.
10. Zhong, Y. F.; Han, X. Y.; Li, S. B.; Qi, H.; Zhou, Z. H. Chem. Reagents 2017, 39, 578-582.
11. Belavagi, N. S.; Sunagar, M. G.; Lamani, R. S.; Deshapande, N.; Khazi, I. A. M. Phosphorus Sulfur Silicon Relat. Elem. 2015, 190, 1580-1587.
12. Rajyalakshmi, G.; Reddy, A. R. N.; Sarangapani, M. Toxicol. Environ. Chem. 2012, 94, 2006-2011.
13. Zheng, Y. T.; Zhang, T. T.; Wang, P. Y.; Wu, Z. B.; Zhou, L.; Ye, Y. Q.; Zhou, X.; He, M.; Yang, S. Chin. Chem. Lett. 2017, 28, 253-256.
14. Li, P.; Shi, L.; Yang, X.; Yang, L.; Chen, X. W.; Wu, F.; Shi, Q. C.; Xu, W. M.; He, M. Bioorg. Med. Chem. Lett. 2014, 24, 1677-1680.
15. Wang, P. Y.; Chen, L.; Zhou, J.; Fang, H. S.; Wu, Z. B.; Song, B. A.; Yang, S. J. Saudi Chem. Soc. 2017, 21, 315-323.
16. Song, X. P.; Li, P.; Li, M. W.; Yang, A. M.; Yu, L.; Luo, L. Z.; Hu, D. Y.; Song, B. A. Pestic. Biochem. Phys. 2017, 147, 11-19.
17. Bachwani, M.; Sharma, V.; Kumar, R. Synth. Commun. 2017, 47, 1805-1847.
18. Kumar, S. Turk. J. Chem. 2011, 35, 99-108.
19. Dürüst, Y.; Karakuş, H.; Yavuz, M. Z.; Gepdiremen, A. A. Turk. J. Chem. 2014, 38, 739-755.
20. Alp, A. S.; Kılcıgil, G.; Özdamar, E. D.; Çoban, T.; Eke, B. Turk. J. Chem. 2014, 39, 42-53.
21. Guo, Y.; Qu, L.; Wang, X.; Huang, M. X; Jia, L.; Zhang, Y. B. RSC Adv. 2016, 6, 93505-93510.
22. Liu, Q.; Chen, K.; Wang, Q.; Ni, J.; Li, Y. RSC Adv. 2014, 4, 55445-55451.
23. Xu, F. Z.; Wang, Y. Y.; Luo, D. X.; Yu, G.; Wu, Y. K. ChemistrySelect 2018, 3, 2795-2799.
24. Xu, F. Z.; Wang, Y. Y.; Luo, D. X.; Yu, G.; Guo, S. X. RSC Adv. 2018, 8, 6306-6314.
25. Stoica, C. I.; Ionut, I.; Vlase, L.; Tiperciuc, B.; Marc, G. Biomed. Chromatogr. 2018, 32, e4221.
26. Wu, J.; Kang, S. H.; Luo, L. J.; Shi, Q. C.; Ma, J. Chem. Cent. J. 2013, 7, 64.
27. Xu, W. M.; He, J.; He, M.; Han, F. F.; Chen, X. H. Molecules 2011, 16, 9129-9141.
28. Cui, Z. N.; Shi, Y. X.; Zhang, L.; Ling, Y.; Li, B. J. J. Agric. Food Chem. 2012, 60, 11649-11656.
29. Ji, Z.; Liu, F.; Zhang, Z.; Li, F.; Jiang L. Chin. J. Org. Chem. 2012, 32, 2129-2133.
30. Li, P.; Yin, J.; Xu, W. M.; Wu, J.; He, M. Chem. Biol. Drug Des. 2013, 82, 546-556.
31. Li, P.; Hu, D. Y.; Xie, D. D.; Chen, J. X.; Jin, L. H. J. Agric. Food Chem. 2018, 66, 3093-3100.
32. Patel, P. A.; Bhadani, V. N.; Bhatt, P. V.; Purohit, D. M. J. Heterocycl. Chem. 2015, 52, 1119-1125.
33. Hoekstra, W. J.; Hargrove, T. Y.; Wawrzak, Z.; Batista, D. D. J.; Silva, C. F. Antimicrob. Agents Ch. 2016, 60, 1058-1066.
34. Cazade, M.; Nuss, C. E.; Bidaud, I.; Renger, J. J.; Uebele, V. N. Mol. Pharmacol. 2014, 85, 218-225.
35. Kitagawa, Y.; Tamai, I.; Hamada, Y.; Usui, K.; Wada, M. J. Pharmacol. Sci. 2013, 122, 128-137.
36. Kitagawa, Y.; Miyai, A.; Usui, K.; Hamada, Y.; Deai, K. J. Pharmacol. Exp. Ther. 2012, 342, 520-528.
37. Xu, F. Z.; Wang, Y. Y.; Zhu, Y. Y.; Shao, J. H.; Yu, G. Phosphorus Sulfur Silicon Relat. Elem. 2017, 192, 850-855.