Synthesis and Fungicidal Activity of Methyl 2-Methoxyimino-2-polysubstituted-phenylacetates

doi:10.6023/cjoc201309004

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (4): 774-782.DOI: 10.6023/cjoc201309004 Previous Articles Next Articles

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2-甲氧亚胺基-2-(多取代苯基)乙酸甲酯类化合物合成及杀菌活性

姜文涛, 胡方中, 顾翰, 刘传, 魏乃翔, 万蕾, 任士钊, 王俊婷, 徐凤波

南开大学元素有机化学国家重点实验室元素有机化学研究所天津 300071

收稿日期:2013-09-02 修回日期:2013-12-02 发布日期:2013-12-13
通讯作者: 胡方中，徐凤波 E-mail:fzhu@nankai.edu.cn;xufb@nankai.edu.cn
基金资助:
国家“十二五”科技支撑计划（Nos. 2011BAE06B03-12，2011BAE06B05）、国家自然科学基金（No. 21172114）和天津市自然科学基金（No. 11JCYBJC14200）资助项目.

Synthesis and Fungicidal Activity of Methyl 2-Methoxyimino-2-polysubstituted-phenylacetates

Jiang Wentao, Hu Fangzhong, Gu Han, Liu Chuan, Wei Naixiang, Wan Lei, Ren Shizhao, Wang Junting, Xu Fengbo

State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071

Received:2013-09-02 Revised:2013-12-02 Published:2013-12-13
Supported by:
Project supported by the National “Twelfth Five-Year” Plan for Science & Technology Support (Nos. 2011BAE06B03-12, 2011BAE06B05), the National Natural Science Foundation of China (No. 21172114) and the Natural Science Foundation of Tianjin City (No. 11JCYBJC14200).

Reaction of methyl 2-chloro-2-oxacetate and 4-chlorotoluene (or 3-tert-butyltoluene) in the presence of AlCl₃ in CH₂Cl₂ generated 2-(5-chloro-or 4-tert-butyl-toluene)-2-methyl-phenyl-2-oxoacetate (A), which were treated with O-methyl-hydroxylamine to furnish (Z/E)-methyl-2-(5-chloro (or 4-tert-butyl)-2-methyl phenyl)-2-(methoxyimino)acetates (B). B were brominated with Br₂ to afford the intermediate (Z/E)-ethyl-2-(2-bromomethyl-5-chloro (or 4-tert-butyl)-2-methyl-phenyl)-2-(methoxyimino)acetates (C). The intermediate E-methyl-2-(2-(bromomethyl phenyl)-5-nitro-phenyl)-2-(methoxyimino)acetate (F) was obtained from nitration of E-methyl-2-(2-(bromomethyl)phenyl)-2-(methoxyimino)acetate (E). The intermediates C and F were condensed with various aryl ketoximes to produce the title compounds (D, E and G). Compound H was obtained from the reduction of G1. All of the title compounds have been characterized by ¹H NMR, ¹³C NMR, ¹⁹F NMR, IR and HRMS. All of the title compounds were tested for fungicidal activities against cucumber gray mold, tomato disease early, wheat gibberellic, pepper phytophthora, rape sclerotium, rice grain dry and so forth by the mycelium growth rate method, which indicated that some of them displayed better fungicidal activity than that of trifloxystrobin.

Key words: methoxyl acrylate compounds, synthesis, fungicidal activity

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Jiang Wentao, Hu Fangzhong, Gu Han, Liu Chuan, Wei Naixiang, Wan Lei, Ren Shizhao, Wang Junting, Xu Fengbo. Synthesis and Fungicidal Activity of Methyl 2-Methoxyimino-2-polysubstituted-phenylacetates[J]. Chin. J. Org. Chem., 2014, 34(4): 774-782.

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[1] Beautement, K.; Clough, J. M.; de Fraine, P. J.; Godfrey, C. R. A. Pestic. Sci. 1991, 31, 499.
[2] Sauter, H.; Steglich, W.; Anke, T. Angew. Chem., Int. Ed. 1999, 38, 1329.
[3] Lu, C.-Z.; Liu, J.-H.; Du, X.-H. Agrochemicals 2011, 50, 187 (in Chinese).(陆翠军, 刘建华, 杜晓华, 农药, 2011, 50, 187.)
[4] Zhao, P. Pestic. Alerts 2012, 25 (in Chinese).(赵平, 农药快讯, 2012, 25.)
[5] Li, M.; Liu, C.-L.; Yang, J.-C.; Zhang, J.-B.; Li, Z.-N.; Zhang, H.; Li, Z.-M. J. Agric. Food Chem. 2010, 58, 2664.
[6] Hua, N.-Z. Modern Agrochem. 2013, 12, 6 (in Chinese).(华乃震, 现代农药, 2013, 12, 6.)
[7] Sun, R.-F.; Lu, M..-Y.; Chen, L.; Li, Q.-S.; Song, H.-B.; Bi, F.-C.; Huang, R.-Q.; Wang, Q.-M. J. Agric. Food Chem. 2008, 56, 11376
[8] Zhang, X.; Gao, Y.-X.; Liu, H.-J. Bull. Korean Chem. Soc. 2012, 33, 2627.
[9] Chai, B.; Wen, C.; Chen, X.-D.; Li, Z.-C. Agrochemicals 2013, 52, 258.(柴兵, 闻冲, 陈晓东, 李宗成, 农药, 2013, 52, 258.)
[10] Chung, W. H.; Deepak, S. A.; Ishii, H. J. Gen. Plant Pathol. 2013, 79, 128.
[11] Huang, W.; Zhao, P.-L.; Liu, C.-L.; Chen, Q.; Liu, Z.-M.; Yang, G.-F. J. Agric. Food Chem. 2007, 55, 3004.
[12] 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.)
[13] Bostanian, N. J.; Larocque, N. Phytoparasitica 2011, 29, 215
[14] Li, Q. M.S. Thesis, Tongji University, Shanghai, 2007 (in Chinese).(李倩, 硕士论文, 同济大学, 上海, 2007).
[15] Wang, X.-Y.; Xue, X.-P.; Pang, Y.-P.; Chen, P.-Y.; Min, N.-N.; Dou, Y.-L. J. Jilin Agric. Sci. 2013, 38, 49 (in Chinese).(王献友, 薛潇沛, 庞艳萍, 陈培云, 闵娜娜, 窦玉蕾, 吉林农业科学, 2013, 38, 49.)
[16] Zhao, P.; Yan, Q.-X; Li, X.; Zhang, M.-H. Agrochemicals 2011, 50, 547 (in Chinese).(赵平, 严秋旭, 李新, 张敏恒, 农药, 2011, 50, 547.)
[17] Liu, C.-L.; Zhang, L.-X.; Wang, C.-M.; She, Y.-H. Pesticides 1998, 37, 1 (in Chinese).(刘长令, 张立新, 汪灿明, 佘永红, 农药, 1998, 37, 1.)
[18] Liu, A.-P.; He, H.-J.; Liu, X.-P.; He, L.; Hu, C.-H.; Wei, Z.-Z.; Hu, Z.-B.; Hang, M.-Z.; Ou, X.-M.; Su, S.-P. Chin. J. Org. Chem. 2009, 29, 1381 (in Chinese).(柳爱平, 何海军, 刘兴平, 何莲, 胡春华, 魏振中, 胡志彬, 黄明智, 欧晓明, 苏胜培, 有机化学, 2009, 29, 1381.)
[19] Pascual, A.; Ziegler, H.; Trah, S.; Ertl, P.; Winkler, T. Tetrahedron Lett. 2000, 41, 1381.
[20] Kuroda, Y.; Yamada, M.; Tabushi, I. J. Chem. Soc., Perkin Trans. 2 1989, 1409.
[21] Chen, C.; Liu, A.-P.; Mao, C.-H.; Liu, X.-P. Fine Chem. Intermed. 2004, 34, 25 (in Chinese).(陈灿, 柳爱萍, 毛春辉, 刘兴平, 精细化工中间体, 2004, 34, 25.)
[22] Kikuchi, D.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6023.
[23] Jiri, H.; Illia, P.; Milos, S. Tetrahedron Lett. 2013, 54, 3533.
[24] Judd, L. W.; Davis, A. P. Chem. Commun. 2010, 46, 2227.
[25] Xu, P.-P. M.S. Thesis, Huazhong Normal University, Hubei, 2012 (in Chinese).(徐平平, 硕士论文, 华中师范大学, 湖北, 2012.)
[26] Zhang, X.; Zhang, Y.-J.; Chen, Y.; Zhou, M.-G. Chin. J. Pestic. Sci. 2008, 10, 41 (in Chinese).(张晓, 张艳军, 陈雨, 周明国, 农药学学报, 2008, 10, 41.)

2-甲氧亚胺基-2-(多取代苯基)乙酸甲酯类化合物合成及杀菌活性

Synthesis and Fungicidal Activity of Methyl 2-Methoxyimino-2-polysubstituted-phenylacetates

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