含1,3,4-噻二唑杂环的甲氧基丙烯酸酯类化合物的合成与杀菌活性研究
收稿日期: 2013-07-01
修回日期: 2013-09-02
网络出版日期: 2013-09-06
基金资助
国家重点基础研究发展计划（973计划，No. 2010CB126105）资助项目.
Synthesis and Fungicidal Activity of the Strobilurins Containing 1,3,4-Thiodiazole Ring
Received date: 2013-07-01
Revised date: 2013-09-02
Online published: 2013-09-06
Supported by
Project supported by the National Basic Research Program of China (973 Program, No. 2010CB126105).
袁小勇 , 张鹭 , 韩小强 , 周子原 , 杜士杰 , 万川 , 杨冬燕 , 覃兆海 . 含1,3,4-噻二唑杂环的甲氧基丙烯酸酯类化合物的合成与杀菌活性研究[J]. 有机化学, 2014 , 34(1) : 170 -177 . DOI: 10.6023/cjoc201306032
Sixteen novel strobilurins containing 1,3,4-thiodiazole ring were synthesized by multi-step reactions including acylation, alcoholysis, hydrazinolysis, nucleophilic addition, dehydration and nucleophilic substitution from initial substituted benzoic acid and their structures were characterized by 1H NMR, IR, MS and HRMS. The results of bioassay indicated that the fungicidal activity of title compounds is better against Rhizoctonia solani Kühn and Fusarium oxysporum than Phytophthora infestans in vitro, while remarkably higher when against Colletetrichum orbiculare. Especially, compounds 5a～5c, 5g, 6a～6c displayed higer fungicidal activities than azoxystrobin, the inhibitory rate of 5g is 77.5% at the concentration of 100 μg/mL.
Key words： 1,3,4-thiodiazole; strobilurin; synthesis; fungicidal activitiy
[1] Sauter, H.; Steglich, W.; Anke, T. Angew. Chem., Int. Ed. 1999, 38, 1328.
[2] Bartlett, D. W.; Clough, J. M.; Godwin, J. R.; Hall, A. A.; Hamer, M.; Parrdobrzanski, B. Pest Manage. Sci. 2002, 58, 649.
[3] Zhao, P.-L.; Zhang, B.; Wang, Y.-Z.; Yang, G.-F. Chin. J. Org. Chem. 2008, 28, 875 (in Chinese).
(赵培亮, 章博, 王亚洲, 杨光富, 有机化学, 2008, 28, 875.)
[4] Guan, A.-Y.; Liu, C.-L.; Li, M.; Zhang, H.; Li, Z.-N.; Li, Z.-M. Pest manage. Sci. 2011, 67, 859.
[5] Li, G.-H.; Yang, H. Chin. J. Org. Chem. 2008, 28, 1918 (in Chinese).
(李国华, 杨红, 有机化学, 2008, 28, 1918.)
[6] Ulrich, G.; Helge, S.; Alison, C.; Alan, M. Pest Manage. Sci. 2002, 58, 859.
[7] Julius, S.; Miroslav, B.; Vladimir, M. Biochem. Biophys. Res. Commun. 1974, 57, 17.
[8] Von Jagow, G.; Gribble, G. W.; Trumpower, B. L. Biochemistry 1986, 25, 775.
[9] Reuveni, M. Eur. J. Plant Pathol. 2003, 109, 243.
[10] Underdown, R. S.; Sivasithamparam, K.; Barbettic, M. J. Australas. Plant Pathol. 2003, 37, 335.
[11] Furzer, G. S.; Veldhuis, L; Hall, J. C. J. Agric. Food Chem. 2006, 54, 688.
[12] Esser, L.; Quinn, B.; Li, Y.; Zhang, M.; Elberry, M.; Yu, L.; Yu, C.; Xia, D. J. Mol. Biol. 2004, 341, 281.
[13] Fisher, N.; Meunier, B. Pest. Manage. Sci. 2005, 61, 973.
[14] Gisi, U.; Sierotzki, H.; Cook, A.; McCaffery, A. Pest. Manage. Sci. 2002, 58, 859.
[15] Aspinall, I. H.; Worthington, P. A. Pestic. Sci. 1999, 55, 197.
[16] Li, Y.; Zhang, H.-Q.; Liu, J.; Yang, X.-P.; Liu, Z.-J. J. Agric. Food Chem. 2006, 54, 3636.
[17] Huang, W.; Zhao, P.-L.; Liu, C.-L.; Chen, Q.; Liu, Z.-M.; Yang G.-F. J. Agric. Food Chem. 2007, 55, 3004.
[18] Dai, H.; Yu, H.-B.; Liu, J.-B.; Qin, X.; Wang, T.-T.; Zhang, X.; Qin, Z.-F.; Fang, J.-X. Chin. J. Org. Chem. 2013, 33, 1104 (in Chinese).
(戴红, 于海波, 刘建兵, 秦雪, 王婷婷, 张欣, 秦振芳, 方建新, 有机化学, 2013, 33, 1104.)
[19] Yuan, M.-Y.; Liu, W.-H.; Zhang, Y.-Q.; Yan, H.-F.; Zhang, D.-N.; Liu, H.-M.; Wang, J.-P. Chin. J. Org. Chem. 2013, 33, 1108 (in Chinese).
(袁明月, 刘伟华, 张英群, 闫红飞, 张冬暖, 刘卉闵, 王建平, 有机化学, 2013, 33, 1108.)
[20] Li, N.; Wei, X.; Fan, H.-T.; Bi, L.; Li, X.-Y.; Yang, S.; Hu, D.-Y.; Song, B.-A. Chin. J. Org. Chem. 2011, 31, 1300 (in Chinese).
(李娜, 魏学, 范会涛, 毕亮, 李向阳, 杨松, 胡德禹, 宋宝安, 有机化学, 2011, 31, 1300.)
[21] Yan, M.; Shi, D.-Q. Chin. J. Org. Chem. 2008, 28, 736 (in Chinese).
(严曼, 石德清, 有机化学, 2008, 28, 736.)
[22] Shen, F.; Hu, A.-X.; Luo, X.-F.; Li, J.; Ou, X.-M. Chin. J. Org. Chem. 2012, 32, 388 (in Chinese).
(沈芳, 胡艾希, 罗先福, 叶姣, 欧晓明, 有机化学, 2012, 32, 388.)
[23] Dai, H.; Liu, J.-B.; Miao, W.-K.; Wu, S.-S.; Zhang, X.; Wang, T.-T.; Fang, J.-X. Chin. J. Org. Chem. 2011, 31, 1943 (in Chinese).
(戴红, 刘建兵, 苗文科, 吴珊珊, 张欣, 王婷婷, 方建新, 有机化学, 2011, 31, 1943.)
[24] Ma, Z.-H.; Zhou, M.-G.; Ye, Z.-Y. Acta Phytopathol. Sinica 1997, 27, 237 (in Chinese).
(马忠华, 周明国, 叶钟音, 植物病理学报, 1997, 27, 237.)
[25] Yan, F.-Y.; Liu, D.-Q.; Guan, A.-Y.; Liu, C.-L. Pesticides 2003, 42, 46 (in Chinese).
(颜范勇, 刘冬青, 关爱莹, 刘长令, 农药, 2003, 42, 46.)
[26] Liu, Y.-P.; Yang, J.-C.; Chai, B.-S.; Wu, Q.; Liu, C.-L. Agrochemicals 2011, 50, 756 (in Chinese).
(刘允萍, 杨吉春, 柴宝山, 吴峤, 刘长令, 农药, 2011, 50, 756.)
[27] Song, B.-A.; Chen, C.-J.; Yang, S.; Jin, L.-H.; Xue, W.; Zhang, S.-M.; Zou, Z.-H.; Hu, D.-Y.; Liu, G. Acta Chim. Sinica 2005, 63, 1720 (in Chinese).
(宋宝安, 陈才俊, 杨松, 金林红, 薛伟, 张素梅, 邹志辉, 胡德禹, 刘刚, 化学学报, 2005, 63, 1720.)
[28] Gilani, S. J.; Khan, S. A.; Siddiqui, N. Bioorg. Med. Chem. Lett. 2010, 20, 4762.
[29] Wu, X.-L.; Zhu, C.-F.; Lu, Z.-D.; Wei, C.-S.; Liao, X.-C. Chin. J. Org. Chem. 2011, 31, 824 (in Chinese).
(武现丽, 朱春风, 吕志丹, 魏成事, 廖新成, 有机化学, 2011, 31, 824.)
[30] Fabio, L. M.; Thomas, K.; Gu, J. M.; Martin, B.; Johannes, P.; Ana, F.; Juan, M. D.; Batya, P.; Hagit, E.-F.; Boris, S. Eur. J. Med. Chem. 2013, 61, 26.
[31] Yao, M.-X.; An, Y.; Yan, J.; Tian, X.; Wei, S. Chin. J. Org. Chem. 2013, 33, 1015 (in Chinese).
(姚明星, 安悦, 闫杰, 田星, 魏诗, 有机化学, 2013, 33, 1015.)
[32] Zhu, S.-S.; Lu, J.-R.; Xin, C.-W.; Lu, B.-W.; Bao, X.-R.; Tang, D.-W.; Zou, M.; Liu, Q. Chin. J. Org. Chem. 2010, 30, 1914 (in Chinese).
(朱姗姗, 卢俊瑞, 辛春伟, 卢博为, 鲍秀荣, 唐大伟, 邹敏, 刘倩, 有机化学, 2010, 30, 1914.)
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