Design, Synthesis and Biological Activities of Amides(Sulfonamides) Containing N-Pyridylpyrazole

doi:10.3969/j.issn.0251-0790.2012.02.015

Abstract

Abstract: Referring to the structure of Rynaxypyr^TM, a series of novel amides(sulfonamides) containing N-pyridylpyrazole was designed and synthesized. Their chemical structures were characterized by means of ¹H NMR and elemental analysis. The results of the biological assay show that some of the amide(subfonamides) exhibite good insecticidal activities against Oriental Armyworm(Mythimna separata Walker) and Culex pipiens pallens. The death rates for Oriental Armyworm of compounds 4a, 4k and 5b are all higher than 50% at 100 mg/L, and the death rate of compound 4g for Culex pipiens pallens was 100% at 2 mg/L.

Key words: Rynaxypyr^TM, Amide, Sulfonamide, Biological activity

CLC Number:

O625

TrendMD:

XU Jun-Ying, DONG Wei-Li, XIONG Li-Xia, LI Zheng-Ming. Design, Synthesis and Biological Activities of Amides(Sulfonamides) Containing N-Pyridylpyrazole[J]. Chem. J. Chinese Universities, 2012, 33(02): 298.

References

[1] Lahm G. P., Mvis B. J., Selby T. P.. Insecticidal Anthranilamides, WO 2001070671[P], 2001-09-27 [2] Lahm G. P., Selby T. P., Stevenson T. M.. Arthropodicidal Anthranilamides, WO 2003015519[P], 2003-02-27 [3] Lahm G. P., Selby T. P., Freudenberger J. H., Stevenson T. M., Myers B. J., Seburyamo G. S., Smith B. K., Flexner L., Clark C. E., Cordova D.. Bioorg. Med. Chem. Lett.[J], 2005, 15(22): 4898-4906 [4] Ebbinghaus-Kintscher U., Luemmena P., Lobitz N., Schulte T., Funke C., Fischer R., Masaki T., Yasokawa N., Tohnishi M.. Cell Calcium[J], 2006, 39(1): 21-33 [5] OU Xiao-Ming(欧晓明), TANG De-Xiu(唐德秀), LIN Xue-Mei(林雪梅). World Pesticides(世界农药)[J], 2007, 29(5): 6-10 [6] Hughes K. A., Lahm G. P., Selby T. P.. Cyano Anthranilamide Insecticides, WO 2004067528[P], 2004-08-12 [7] Berrisge M. J., Lipp P., Bootman M. D.. Nat. Rev. Mol. Cell. Biol.[J], 2000, 1(1): 11-21 [8] FENG Qi(冯启), LIU Zhi-Li(刘智力), WANG Ming-Zhong(王明忠), XIONG Li-Xia(熊丽霞), YU Shu-Jing(于淑晶), Li Zheng-Ming(李正名). Chem. J. Chinese Universities(高等学校化学学报)[J], 2011, 32(1): 74-78 [9] DONG Wei-Li(董卫莉), XU Jun-Ying(徐俊英), LIU Xing-Hai(刘幸海), LI Zheng-Ming(李正名), LI Bao-Ju(李宝聚), SHI Yan-Xia(石延霞). Chem. J. Chinese Universities(高等学校化学学报)[J], 2008, 29(10): 1990-1994 [10] DONG Wei-Li(董卫莉), LIU Xing-Hai(刘幸海), XU Jun-Ying(徐俊英), LI Zheng-Ming(李正名). J. Chem. Res.(S)[J], 2008, 9: 530-533 [11] LIU Xing-Hai(刘幸海), CHEN Pei-Quan(陈沛全), WANG Bao-Lei(王宝雷), LI Yong-Hong(李永红), WANG Su-Hua(王素华), LI Zheng-Ming(李正名). Bioorg. Med. Chem. Lett.[J], 2007, 17(13): 3784-3788 [12] Shapiro R., Taylor E. G., Zimmerman W.T.. Method for Preparing N-Phenylpyrazole-1-carboxamides, WO 2006062978[P], 2006-06-15 [13] LI Zai-Guo(李在国), WANG Qing-Min(汪清民), HUANG Jun-Min(黄君珉). Preparation of Organic Intermediates, Second Ed.(有机中间体制备, 第2版)[M], Beijing: Chemical Industry Press, 2001: 97-98, 132 [14] George W. R.. J. Am. Chem. Soc.[J], 1942, 64(10): 2340-2342

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