Synthesis and Insecticidal Activity of Novel Anthranilic Diamides Containing Polyfluoroalkyl Pyrazole Moiety

doi:10.6023/cjoc201701019

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (8): 2131-2138.DOI: 10.6023/cjoc201701019 Previous Articles Next Articles

Notes

含多氟烷基吡唑环的邻甲酰氨基苯甲酰胺类化合物的合成及杀虫活性

史建俊^a, 任贵华^a, 吴宁捷^b, 刘幸海^a, 许天明^b, 谭成侠^a

a 浙江工业大学化学工程学院杭州 310014;
b 中化蓝天集团有限公司浙江省化工研究院有限公司杭州 310023

收稿日期:2017-01-09 修回日期:2017-04-08 发布日期:2017-04-21
通讯作者: 谭成侠 E-mail:tanchengxia@zjut.edu.cn
基金资助:
“十二五”国家科技支撑计划（No.2011BAE06B01-20）资助项目.

Synthesis and Insecticidal Activity of Novel Anthranilic Diamides Containing Polyfluoroalkyl Pyrazole Moiety

Shi Jianjun^a, Ren Guihua^a, Wu Ningjie^b, Liu Xinghai^a, Xu Tianming^b, Tan Chengxia^a

a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014;
b Sinochem Lantian Zhejiang Research Institute of Chemical Industry Co. Ltd, Hangzhou 310023

Received:2017-01-09 Revised:2017-04-08 Published:2017-04-21
Contact: 10.6023/cjoc201701019 E-mail:tanchengxia@zjut.edu.cn
Supported by:
Project supported by the National Key Technologies R&D Program of China during the 12th Five-Year Plan Period (No. 2011BAE06B01-20).

1. Synthesis and Insecticidal Activity of Novel Anthranilic Diamides Containing Polyfluoroalkyl Pyrazole Moiety.PDF(1581KB)

Abstract

A series of novel anthranilic diamides containing polyfluoroalkyl pyrazole were synthesized using 2,3-dichloropyridine and hydrazine hydrate as starting materials via substitution, condensation, oxidation, etherification, cyclization and ring cleavage reaction. The title products were characterized by ¹H NMR and HRMS. The bioassay results indicated that most of title compounds exhibited 100% insecticidal activitiy against Mythimna separata Walker at 0.8 mg/L, N-(4-chloro-2-(isopropylcarbamoyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-3-((1-methyl-3-(perfluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl)oxy)-1H-pyrazole-5-carboxamide (8c) and N-(4-chloro-2-(cyclopropylcarbamoyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-3-((1-methyl-3-(perfluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-yl)oxy)-1H-pyrazole-5-carboxamide (8d) showed more than 60% larvicidal activity against Prodenia litura Fabricius at 2 mg/L, and the mortality of N-(4-chloro-2-(dimethylcarbamoyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-3-((1-methyl-3-(perfluoroethyl)-4-(trifluoromethyl)-1Hpyrazol-5-yl)oxy)-1H-pyrazole-5-carboxamide (8l) against Plutella xylostella Linnaeus reached 82.5% at 0.08 mg/L.

Key words: polyfluoroalkyl pyrazole, anthranilic diamide, synthesis, insecticidal activity

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Shi Jianjun, Ren Guihua, Wu Ningjie, Liu Xinghai, Xu Tianming, Tan Chengxia. Synthesis and Insecticidal Activity of Novel Anthranilic Diamides Containing Polyfluoroalkyl Pyrazole Moiety[J]. Chin. J. Org. Chem., 2017, 37(8): 2131-2138.

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[1] Oerke, E. C. J. Agric. Sci. 2006, 144, 31.
[2] Wang, B. L.; Zhu, H. W.; Ma, Yi.; Xiong, L. X.; Li, Y. Q.; Zhao, Y.; Zhang, J. F.; Chen, Y. W.; Zhou, S.; Li, Z. M. J. Agric. Food Chem. 2013, 61, 5483.
[3] Cordova, D.; Benner, E. A.; Sacher, M. D.; Rauh, J. J.; Sopa, J. S.; Lahm, G. P.; Selby, T. P.; Stevenson, T. M.; Flexner, L.; Gutteridge, S.; Rhoades, D. F.; Wu, L.; Smith, R. M.; Tao, Y. Pestic. Biochem. Physiol. 2006, 84, 196.
[4] Clark, D, A.; Lahm, G. P.; Smith, B. K.; Barry, J. D.; Clagg, D. G. Bioorg. Med. Chem. 2008, 16, 3163.
[5] Wu, J.; Song, B. A.; Hu, D. Y.; Yue, M.; Yang, S. Pest Manage. Sci. 2012, 68, 801.
[6] Zhang, J. F.; Xu, J. Y.; Wang, B. L.; Li, Y. X.; Xiong, L. X.; Li, Y. Q.; Ma, Y.; Li, Z, M. J. Agric. Food Chem. 2012, 60, 7565.
[7] Chen, K.; Liu, Q.; Ni, P. J.; Zhu, H. J.; Lia, Y. F.; Wang, Q. Pest Manage. Sci. 2015; 71, 1503.
[8] Lahm, G. P.; Stevenson, T. M.; Selby, T. P.; Freudenberger, J. H.; Cordova, D.; Flexner, L.; Bellin, C. A.; Dubas, C. M.; Smith, B. K.; Hughes, K. A.; Hollingshaus, J. G.; Clark, C. E.; Benner, E. A. Bioorg. Med. Chem. Lett. 2007, 17, 6274.
[9] Hughes, K. A.; Lahm, G. P.; Selby, T. P.; Stevenson, T. M. WO 2004067528, 2004[Chem. Abstr. 2004, 141, 190786].
[10] Joseph, S. V.; Grettenberger, I.; Godfrey, L. Crop Prot. 2016, 87, 68.
[11] Weller, P.; Boner M.; Foerstel, H.; Becker, H.; Peikert, B.; Dreher, W. J. Agric. Food Chem. 2011, 59, 4365.
[12] Motoba, K.; Nishizawa, H.; Suzuki, T.; Hamaguchi, H.; Uchida, M.; Funayama, S. Pestic. Biochem. Physiol. 2000, 67, 73.
[13] Monicka, J. C.; James, C. J. Mol. Struct. 2014, 1075, 335.
[14] Quayle, W. C.; Oliver, D. P.; Zrna. S.; Fattore, A. J. Agric. Food Chem. 2007, 55, 5199.
[15] Chupp, J. P.; Hamper, B. C.; Wettach, R. H. WO 9602515, 1996[Chem. Abstr. 1996, 125, 10808].
[16] Wang, W. Q.; Zhang. P.; Meng, R. J.; Zhao, J. J.; Huang, Q. L.; Han, X. Y.; Ma, Z. Q.; Zhang, X. F. Crop Prot. 2014, 57, 48.
[17] Fulcher, J. M.; Wayment, D. G.; White Jr., P. M.; Webber Ⅲ, C. L.J. Agric. Food Chem. 2014, 62, 2141.
[18] Maue, M.; Decor, A.; Bretschneider, T.; Hahn, J. J.; Hallenbach, W.; Fischer, R.; Schwarz, H. G.; Gorgens, U.; Ilg, K.; Raming, K.; Kobberling, J.; Hubsch, W.; Turberg, A. WO 2015193218, 2015[Chem. Abstr. 2015, 164, 127051].
[19] Thielert, W.; Maue, M.; Pitta, L.; Weckwert, H. WO 2015132168, 2015[Chem. Abstr. 2015, 163, 408360].
[20] Maue, M.; Harschneck, T.; Fisher, R.; Bretschneider, T.; Haha, J. J.; Decor, A.; Hallenbach, W.; Schwarz, H. G.; Kobberling, J.; Hubbsch, W. WO 2016020441, 2016[Chem. Abstr. 2016, 164, 290366].
[21] Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Yuan, J.; Yang, G.; Xu, T. M.; Peng, W. L. Bioorg. Med. Chem. Lett. 2016, 26, 3626.
[22] Zhao, W.; Xing, J. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. Front. Chem. Sci. Eng. 2017, 11, 291.
[23] Zhao, W.; Shen, Z. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. Lett. Drug Des. Discovery 2017, 14, 323.
[24] Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L. Eur. J. Med. Chem. 2017, 125, 881.
[25] Zhao, W.; Shen, Z. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. J. Heterocycl. Chem. 2017, 54, 1751.
[26] Zhai, Z. W.; Wang, Q.; Shen, Z. H.; Tan, C. X.; Weng, J. Q.; Liu, X. H. Chin. J. Org. Chem. 2017, 37, 232(in Chinese). (翟志文, 汪乔, 沈钟华, 谭成侠, 翁建全, 刘幸海, 有机化学, 2017, 37, 232.)
[27] Tan, C. X.; Shi, Y. X.; Liu, X. H.; Li, B. J.; Zhao, W. G. Lett. Drug Des. Discovery 2012, 9, 431.
[28] Gong, Y. Y.; Huang, W.; Liu, X. H.; Weng, J. Q.; Tan, C. X. Chin. J. Org. Chem. 2013, 33, 2396(in Chinese). (贡云芸, 黄伟, 刘幸海, 翁建全, 谭成侠, 有机化学, 2013, 33, 2396.)
[29] Ni, 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). (倪芸, 许天明, 钟良坤, 孔晓燕, 史建俊, 刘幸海, 孔小林, 姬文娟, 谭成侠, 有机化学, 2015, 35, 2218.)
[30] Tan, C. X.; Schrader, K. K.; Mizuno, C. S.; Rimando, A. M. J. Agric. Food Chem. 2011, 59, 5977.
[31] Zhao, Y.; Xiong, L. X.; Xu, L. P.; Wang, H. X.; Xu, H.; Li, H. B.; Tong, J.; Li, Z. M. Res. Chem. Intermed. 2013, 39, 3071.
[32] Zhao, Y.; Xu, L. P.; Tong J; Li, Y. Q.; Xiong, L. X.; Li, F.; Peng L. N.; Li, Z. M. Mol. Diversity 2012, 16, 711.
[33] Wu. J.; Xie, D. D.; Shan, W. L.; Zhao, Y. H.; Zhang, W.; Song, B. A.; Yang, S.; Ma. J. Chem. Pap. 2015, 69, 993.
[34] Berger, R., A.; Flexner, J. L. WO 2003024222, 2003[Chem. Abstr. 2003, 138, 267201].
[35] Zhou, S.; Zhang, X. L.; Wei, W.; Liu, J. B.; Xiong, L. X.; Yang N.; Li, Z. M. Chin. J. Org. Chem. 2014, 34, 1424(in Chinese). (周莎, 张秀兰, 魏巍, 刘敬波, 熊丽霞, 杨娜, 李正名, 有机化学, 2014, 34, 1424.)

含多氟烷基吡唑环的邻甲酰氨基苯甲酰胺类化合物的合成及杀虫活性

Synthesis and Insecticidal Activity of Novel Anthranilic Diamides Containing Polyfluoroalkyl Pyrazole Moiety

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