Syntheses and biological activities of novel 3-bromo-1-(3-chloropyridin-2-yl)-N-hydroxy-N-aryl-1H-pyrazole-5-carboxamides

Hongwei Zhu , Baolei Wang , Xiulan Zhang , Lixia Xiong , Shujing Yu , Zhengming Li

Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (3) : 409 -414.

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Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (3) : 409 -414. DOI: 10.1007/s40242-014-3376-8
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Syntheses and biological activities of novel 3-bromo-1-(3-chloropyridin-2-yl)-N-hydroxy-N-aryl-1H-pyrazole-5-carboxamides

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Abstract

A series of novel 3-bromo-1-(3-chloropyridin-2-yl)-N-hydroxy-N-aryl-1H-pyrazole-5-carboxamides was synthesized by the reaction of pyrazole carbonyl chloride with each of substituted phenylhydroxyamines. The latter ones were prepared in good yields by reducing substituted nitrobenzene compounds with Zn/NH4Cl reductant system in alcohol. Structures of the title compounds were determined by IR, 1H NMR, and HRMS. Their insecticidal and fungicidal activities were evaluated by larvicidal test against oriental armyworm and the mycelium growth rate method, respectively.

Keywords

N-Hydroxyl amide / N-Pyridylpyrazole / Insecticidal activity / Fungicidal activity

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Hongwei Zhu, Baolei Wang, Xiulan Zhang, Lixia Xiong, Shujing Yu, Zhengming Li. Syntheses and biological activities of novel 3-bromo-1-(3-chloropyridin-2-yl)-N-hydroxy-N-aryl-1H-pyrazole-5-carboxamides. Chemical Research in Chinese Universities, 2014, 30(3): 409-414 DOI:10.1007/s40242-014-3376-8

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References

[1]

Abdel-Megeed M F, Badr B E, Azaam M M, El-Hiti G A. Phosphorus Sulfur Silicon Relat. Elem., 2012, 187(17): 1462.

[2]

Shortnacy-Fowler A T, Tiwari K N, Montgomery J A, Buckheit R W Jr., Secrist J A, Seela F. Helv. Chim. Acta, 1999, 82(12): 2570.

[3]

Magedov I V, Manpadi M, van Slambrouck S, Steelant W F A, Rozhkova E, Przheval’skii N M, Rogelj S, Kornienko A. J. Med. Chem., 2007, 50(21): 5183.

[4]

Sardar S, Akhtar T, Hameed S, Khan K M. J. Chem. Soc. Pakistan, 2012, 34(6): 1531.

[5]

Bhuyan P J, Borah H N, Sandhu J S. Tetrahedron Lett., 2002, 43(5): 895.

[6]

Shiga Y, Okada I, Ikeda Y, Takizawa E, Fukuchi T. J. Pestic. Sci., 2003, 28(3): 313.

[7]

Wang B L, Ma Y, Xiong L X, Li Z M. Chin. J. Chem., 2012, 30(4): 815.

[8]

Sauter H, Steglich W, Anke T. Angew. Chem. Int. Ed., 1999, 38(10): 1328.

[9]

Liu X H, Tan C X, Weng J Q. Phosphorus Sulfur Silicon Relat. Elem., 2011, 186(3): 558.

[10]

Ohno R, Watanabe A, Matsukawa T, Ueda T, Sakurai H, Hori M, Hirai K. J. Pestic. Sci., 2004, 29(1): 15.

[11]

Vicentini C B, Mares D, Tartari A, Manfrini M, Forlani G. J. Agric. Food Chem., 2004, 52(7): 1898.

[12]

Liu X H, Tan C X, Weng J Q. Phosphorus Sulfur Silicon Relat. Elem., 2011, 186(3): 552.

[13]

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(22): 6274.

[14]

Wang B L, Zhu H W, Ma Y, 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(23): 5483.

[15]

Hughes K. A., Lahm G. P., Selby T. P., Stevenson T. M., Preparation of Cyano Anthranilamide Insecticides, WO2004067528, 2004

[16]

Yan T, Yu S, Liu P, Liu Z, Wang B, Xiong L, Li Z M. Chin. J. Chem., 2012, 30(4): 919.

[17]

Liu X H, Tan C X, Weng J Q. Asian J. Chem., 2011, 23(9): 4064.

[18]

Zhang X L, Wang B L, Mao M Z, Xiong L X, Yu S J, Li Z M. Chem. J. Chinese Universities, 2013, 34(1): 96.

[19]

Weng J Q, Wang L, Liu X H. J. Chem. Soc. Pakistan, 2012, 34(5): 1248.

[20]

Aulabaugh A, Schloss J V. Biochemistry, 1990, 29(11): 2824.

[21]

Wang B L, Li Z M, Li Y H, Wang S H. Chem. Res. Chinese Universities, 2007, 23(3): 280.

[22]

Lutwick G D, Ryan D E. Can. J. Chem., 1954, 32(10): 949.

[23]

Mangoldt B L K, Hanna P E. J. Med. Chem., 1982, 25(6): 630.

[24]

Brink C P, Crumbliss A L. J. Org. Chem., 1982, 47: 1171.

[25]

Liu X H, Weng J Q, Tan C X. J. Chem., 2013, 306361.

[26]

Tan C X, Shi Y X, Weng J Q, Liu X H, Li B J, Zhao W G. Lett. Drug Des. Discov., 2012, 9(4): 431.

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