Synthesis and Biological Activity of Anthranilic Diamide Derivatives Incorporating 1,3,4-oxadiazole or Nitrogen-containing Saturated Heterocyclic Moieties
Wen-Juan Zhou
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025 People's Republic of China
Search for more papers by this authorLi Zhang
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025 People's Republic of China
Search for more papers by this authorWei Xiao
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025 People's Republic of China
Search for more papers by this authorHe-Ju Chen
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025 People's Republic of China
Search for more papers by this authorWen-Neng Wu
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025 People's Republic of China
Search for more papers by this authorCorresponding Author
Gui-Ping Ouyang
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025 People's Republic of China
E-mail: [email protected]Search for more papers by this authorWen-Juan Zhou
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025 People's Republic of China
Search for more papers by this authorLi Zhang
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025 People's Republic of China
Search for more papers by this authorWei Xiao
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025 People's Republic of China
Search for more papers by this authorHe-Ju Chen
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025 People's Republic of China
Search for more papers by this authorWen-Neng Wu
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025 People's Republic of China
Search for more papers by this authorCorresponding Author
Gui-Ping Ouyang
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang, 550025 People's Republic of China
E-mail: [email protected]Search for more papers by this authorAbstract
A series of novel anthranilic diamide derivatives incorporating 1,3,4-oxadiazole or nitrogen-containing saturated heterocyclic moieties were synthesized, characterized, and evaluated for bacteriostatic activity against three phytopathogenic bacteria Xanthomonas oryzae pv. Oryzae (Xoo), Xanthomonas axonopodis pv. Citri (Xac), Ralstonia solanacearum (R. solanacearum). The preliminary biological results indicated that most compounds exhibit bacteriostatic activity against three phytopathogenic bacteria. Among these compounds, compounds 6g, 6f, and 6i displayed better antibacterial activity. In the test with concentration of 200 µg/mL, antibacterial activity of compound 6i and 6j was 96%. In particular, the bacteriostatic activity displayed by compound 6h against Xoo is similar to the one displayed by commercial drug bismerthiazol.
References and Notes
- 1Wang, 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. Agric Food Chem 2013, 61, 5483.
- 2Lahm, G. P.; Cordova, D.; Barry, J. D. Bioorg Med Chem 2009, 17, 4127.
- 3Mao, M. Z.; Li, Y. X.; Zhou, Y. Y.; Zhang, X. L.; Liu, Q. X.; Di, F. J.; Song, H. B.; Xiong, L. X.; Li, Y. Q.; Li, Z. M. Agric Food Chem 2014, 62, 1536.
- 4Feng, Q.; Liu, Z. L.; Xiong, L. X. Agric Food Chem 2010, 58, 12327.
- 5Zhao, Y.; Li, Y. Q.; Xiong, L. X. Chem Res Chin Univ 2013, 29, 51.
- 6Mao, M. Z.; Li, Y. X.; Liu, Q. X. Bioorg Med Chem Lett 2013, 23, 42.
- 7Liu, C.; Zhang, J. F.; Zhou, Y. Y. Chem Res Chin Univ 2014, 30, 228.
- 8Li, Y. H.; Zhu, H. J.; Chen, K. Org Biomol Chem 2013, 11, 3979.
- 9Mao, M. Z.; Li, Y. X.; Zhou, Y. Y. Agric Food Chem 2014, 62, 1536.
- 10Chen, Q. C.; Xiong, L. X.; Luo, M.; Wang, J.; Hu, C. G.; Zhang, X.; Yu, S. J.; Li, Y. H.; Sun, D. Q. Molecules 2015, 20, 3854.
- 11Liu, C. L.; Chin, J. Pestic 2009, 48, 60.
- 12Ge, Q. J.; Chen, L. Z.; Du, X. H. Chin J Org Chem 2011, 31, 1510.
- 13Zhao, P. L.; Wang, F.; Zhang, M. Z.; Liu, Z. M.; Huang, W.; Yang, G. F. J Agric Food Chem 2008, 56, 10767.
- 14Sun, Y. F.; Li, Y. Q.; Ling, Y.; Yu, H. L.; Yang, S. X.; Yang, X. L. Chin J Org Chem 2011, 31, 1425.
- 15Zhao, P. L.; Wang, L.; Zhu, X. L.; Huang, X. Q.; Zhan, C. G.; Wu, J. W.; Yang, G. F. J Am Chem Soc 2010, 132, 185.
- 16Gao, Y. L.; Lin, X. F.; Han, F. F.; Bao, X. P. Chin J Org Chem 2011, 31, 1648.
- 17Rashad, A. E.; Hegab, M. I.; Abdel-Megeid, R. E.; Micky, J. A.; Abdel-Megeid, F. M. E. Bioorg Med Chem 2008, 16, 7102.
- 18Rizk, H. F.; EI-Badawi, M. A.; Ibrahim, S. A.; EI-Borai, M. A. Chin J Chem 2011, 29, 1451.
- 19Li, Y. X.; Ling, L.; Chen, Q. Chin J Org Chem 2011, 31, 306.
- 20Liu, Z.; Yang, G.; Qin, X. J Chem Technol Biotechnol 2001, 76, 1154.
- 21Jiang, J.; Tan, Y.; Zhu, X.; Wang, Z.; Zuo, Y.; Chen, Q.; Xi, Z.; Yang, G. Agric Food Chem 2010, 58, 2643.
- 22Chen, H. S.; Li, Z. M.; Han, Y. F. Agric Food Chem 2000, 48, 5312.
- 23Joshi, S. D.; Vagdtvi, H. M.; Vaidya, V. P. Eur J Med Chem 2008, 43(9), 1989.
- 24Qian, X.; Zhang, R. J Chem Tech Biotech 1996, 67, 124.
- 25Cao, S.; Qian, X.; Song, G.; Chai, B.; Jiang, Z. Agric Food Chem 2003, 51, 152.
- 26Qu, J. J.; Zhu, X. K.; Wang, L.; Xu, C.; Liu, F.; Ren, L.; Xu, X. B.; Wang, Y.; Rui, C. H.; Liu, S. Z. Agric Food Chem 2012, 60, 10942.
- 27Zhang, J. F.; Xu, J. Y.; Wang, B. L.; Li, Y. X.; Xiong, L. X.; Li, Y. Q.; Ma, Y.; Li, M. Z. Agric Food Chem 2012, 60, 7565.
- 28Donald, P.; Everette, L. M.; Frank, D. P. J Am Chem Soc 1940, 62, 2818.
10.1021/ja01867a055 Google Scholar
- 29Aggarwal, N.; Kumar, R.; Dureja, P.; Khurana, J. M. Chem Biol Drug Des 2012, 79, 384.
- 30Xu, W. M.; Han, F. F.; He, M.; Hu, D. Y.; He, J.; Yang, S.; Song, B. A. J Agric Food Chem 2012, 60, 1036.