Synthesis and Fungicidal Activity of Diamide Compounds Based on the Metabolite of Benalaxyl
- Corresponding author: Jin Shuhui, shuhuij@cau.edu.cn Zhang Jianjun, zhangjianjun@cau.edu.cn
Citation:
Sun Guoshao, Wang Lingna, Jin Shuhui, Dong Yanhong, Lu Huizhe, Zhang Jianjun. Synthesis and Fungicidal Activity of Diamide Compounds Based on the Metabolite of Benalaxyl[J]. Chinese Journal of Organic Chemistry,
;2017, 37(1): 157-165.
doi:
10.6023/cjoc201608006
Dong, X. X. Med. Philos. 1989, 2, 55(in Chinese).
Lu, Y. L.; Diao, J. L.; Gu, X.; Zhang, Y. F.; Xu, P.; Wang, P.; Zhou, Z. Q. Chirality 2011, 23, 424.
doi: 10.1002/chir.v23.5
Yaacoby, T.; Hall, J. C.; Stephenson, G. R. Pestic. Biochem. Physiol. 1991, 41, 296.
doi: 10.1016/0048-3575(91)90084-Y
Karmakar, R.; Ramcharan, B.; Gita, K. J. Agric. Food Chem. 2009, 57, 6369.
doi: 10.1021/jf9008394
Zhang, M. M.; Sun, K.; Wu, H. F.; Yang, H.; Zhang, H.; Zhang, J.; Yang, H. X. Agrochemicals 2010, 49, 94(in Chinese).
Chen, Y. W.; Wan, Y. Y.; Liu, Q. X.; Liu, J. B.; Xiong, L. X.; Yu, S. J.; Li, Z. M. Chin. J. Org. Chem. 2014, 34, 882(in Chinese).
Liu, Q. X.; Huang, M. Z.; Liu, A. P.; Nie, S. Q.; Lei, M. X.; Ren, Y. G.; Pei, H.; He, L. Y.; Hu, L.; Hu, A. X. Chin. J. Org. Chem. 2014, 34, 118(in Chinese).
doi: 10.6023/cjoc201307017
Xie, F.; Liu, T. T.; Yang, G.; Yuan, J.; Kong, X. L.; Xu, T. M.; Tan, C. X. Chin. J. Org. Chem. 2013, 33, 2596(in Chinese).
doi: 10.6023/cjoc201307006
Ning, L. H.; Peng, H.; Xu, H. Y.; He, H. W. Chin. J. Pestic. Sci. 2004, 6, 74(in Chinese).
Liu, T. T.; Nie, Y.; Zhong, L. K.; Huang, H. Y.; Hu. W. Q.; Xu, T. M.; Tan, C. X. Chin. J. Org. Chem. 2015, 35, 422(in Chinese).
doi: 10.6023/cjoc201406017
Chen, Z. X.; Wei, M. X.; Li, X. Q.; Li, T. C.; Zhou, X. Z. Chin. J. Org. Chem. 2015, 35, 835(in Chinese).
doi: 10.6023/cjoc201410013
Zhang, D. Q.; Xu, G. F.; Liu, Y. H.; Wang, D. Q.; Yang, X. L.; Yuan, D. K. Chin. J. Org. Chem. 2015, 35, 2191(in Chinese).
doi: 10.6023/cjoc201505026
Nie, Y.; Xu, T. M.; Zhong, L. K.; Kong, X. Y.; Shi, J. J.; Liu, X. H.; Kong, X. L.; Ji, W. J.; Tan, C. X. Chin. J. Org. Chem. 2015, 35, 2218(in Chinese).
doi: 10.6023/cjoc201504025
Zhang, H.; Liu, R. Q.; Li, Q. B.; Li, Q. Y.; Chen, Y. H.; Liu, K. C.; Liu, S. Z. Chin. J. Org. Chem. 2015, 35, 1506(in Chinese).
doi: 10.6023/cjoc201501040
Gao, Y. X.; Chen, J. H.; Liu, C.; Lv, X. T.; Li, J. Z.; Guo, B. Y. J. Agric. Food Chem. 2013, 61, 9045
doi: 10.1021/jf4020125
Paolo, C.; Marco, M.; Filippo, M. P. J. Chromatogr. 1987, 391, 334.
doi: 10.1016/S0021-9673(01)94334-1
Liu, M. K.; Liu, D. H.; Xu, Y. G.; Jing, X.; Zhou, Z. Q.; Wang, P. J. Agric. Food Chem. 2015, 61, 5205.
Zhang, X.; Zhang, Y. J.; Chen, Y.; Zhou, M. G. Chin. J. Pestic. Sci. 2008, 10, 41(in Chinese).
Freeman, G. A.; Andrews Ⅲ, C. W.; Hopkins, A. L.; Lowell, G. S.; Schaller, L. T.; Cowan, J. R.; Gonzales, S. S.; Koszalka, G. W.; Hazen, R. J.; Boone, L. R.; Ferris, R. G.; Creech, K. L.; Roberts, G. B.; Short, S. A.; Weaver, K.; Reynolds, D. J.; Milton, J.; Ren, J. S.; Stuart, D. I.; Stammers, D. K.; Chan, J. H. J. Med. Chem. 2004, 47, 5923.
doi: 10.1021/jm040072r
Noboru, S.; Toshio, U. Bull. Fac. Agric., Meiji Univ. 1986, 47.
Renhowe, P. A.; Pecchi, S.; Shafer, C. M.; Machajewski, T. D.; Jazan, E. M.; Taylor, C.; Antonios-McCrea, W.; McBride, C. M.; Frazier, K.; Wiesmann, M.; Lapointe, G. R.; Feucht, P. H.; Warne, R. L.; Heise, C. C.; Menezes, D.; Aardalen, K.; Ye, H. L.; He, M.; Le, V.; Vora, J.; Jansen, J. M.; Wernette-Hammond, M. E.; Harris, A. L. J. Med. Chem. 2009, 52, 278.
doi: 10.1021/jm800790t
Tamura, H.; Matsuda, T.; Komiyama, T. JP 51126127, 1976[Chem. Abstr. 1977, 87, 9352].
Goodfellow, V. S.; Settineri, M.; Lawton, R. G. Biochemistry 1989, 28, 6346.
doi: 10.1021/bi00441a030
Ramana Reddy, M. V.; Akula, B.; Cosenza, S. C.; Athuluridivakar, S.; Mallireddigari, M. R.; Pallela, V. R.; Billa, V. K.; Subbaiah, D. R. C. V.; Bharathi, E. V.; Vasquez-Del Carpio, R.; Padgaonkar, A.; Baker, S. J.; Reddy, E. P. J. Med. Chem. 2014, 57, 578.
doi: 10.1021/jm401073p
Bruge, D.; Buchstaller, H. P.; Wiesner, M.; Finsinger, D.; Baumgarth, M.; Sirrenberg, C.; Zenke, F.; Amendt, C.; Grell, M. WO 2005005389, 2005[Chem. Abstr. 2005, 142, 134581].
Anandan, S. K.; Ward, J. S.; Brokx, R. D.; Bray, M. R.; Patel, D. V.; Xiao, X. X. Bioorg. Med. Chem. Lett. 2005, 15, 1969.
doi: 10.1016/j.bmcl.2005.02.075
Pradhan, A.; Pradhan, V.; Jolly, V. S. Orient. J. Chem. 1994, 10, 73.
Veronese, A. C.; Callegari, R.; Morelli, C. F. Tetrahedron 1995, 51, 12277.
doi: 10.1016/0040-4020(95)00773-2
Pareek, A. K.; Joseph, P. E.; SethbDaya, S. Orient. J. Chem. 2009, 25, 681.
Fache, F.; Valot, F.; Milenkovic, A.; Lemaire, M. Tetrahedron 1996, 52, 9777.
doi: 10.1016/0040-4020(96)00503-0
Zheng, L. Y.; Zhang, S. Q.; Zhao, L. F.; Zhu, G. S.; Yang, X. Y.; Gao, G.; Cao, S. G. J. Mol. Catal. B:Enzym. 2006, 38, 119.
doi: 10.1016/j.molcatb.2005.12.003
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7a: R=2, 5-(CF3)2-C6H3; 7b: R=2-Cl-4-CF3-C6H3; 7c: R=C6H5; 7d: R=2-(4-Cl-C6H5)-C6H4; 7e: R=3-CF3-C6H4; 7f: R=2-CN-C6H4; 7g: R=4-C2H5O-C6H4; 7h: R=3-CH3O-C6H4; 7i: R=2-CH3O-C6H4; 7j: R=4-Me-C6H4; 7k: R=4-Cl-C6H4; 7l: R=2-Me-5-F-C6H3; 7m: R=4-Me-3-Cl-C6H3; 7n: R=3-CF3-4-Br-C6H3