Design, Syntheses and Biological Activities of Novel Anthranilic Diamide Insecticides Containing N-Pyridylpyrazole

doi:10.1007/s40242-013-2167-y

Abstract

Abstract:

In search of environmentally benign insecticides with high activity, low toxicity and low residue, a series of novel anthranilic diamide derivatives containing N-pyridylpyrazole was designed and synthesized. All the compounds were characterized by ¹H NMR spectroscopy and elemental analysis. The single crystal structure of compound 8j was determined by X-ray diffraction. The insecticidal activities of the new compounds were evaluated. The results show that some compounds exhibited moderate insecticidal activities against Lepidoptera pests. Among this series of compounds, compounds 8o and 8p showed 100% larvicidal activity against Mythimna separate Walker, Plutella xylostella Linnaeus and Laphygma exigua Hubner at a test concentration of 200 mg/kg, which is equal to the commercial chlorantraniliprole.

Key words: Anthranilic diamide, Ryanodine receptor, Insecticidal activity

ZHAO Yu, LI Yong-qiang, XIONG Li-xia, XU Li-ping, PENG Li-na, LI Fang, LI Zheng-ming. Design, Syntheses and Biological Activities of Novel Anthranilic Diamide Insecticides Containing N-Pyridylpyrazole[J]. Chemical Research in Chinese Universities, 2013, 29(1): 51-56.

References

[1] Tohnishi M., Nakao H., Furuya T., Seo A., Kodama H., Tsubata K., Fujioka S., Kodama H., Hirooka T., Nishimatsu T., J. Pestic. Sci., 2005, 30, 354

[2] Thany S. H., Adv. Exp. Med. Biol., 2010, 683, 75

[3] Legocki J., Polec I., Zelechowski K., Pestycydy. Pesticides, 2010, 59

[4] Coronado R., Morrissette J., Sukhareva M., Vaughan D. M., Am. J. Physiol., 1994, 266, C1485

[5] Sattelle D. B., Cordova D., Cheek T. R., Invert. Neurosci., 2008, 8, 107

[6] Tohnishi M., Nishimatsu T., Motoba K., Hirooka T., Akira S., J. Pestic. Sci., 2010, 35, 490, 508

[7] Tohnishi M., Nakao H., Kohno E., Nishida T., Furuya T., Shimizu T., Seo A., Sakata K., Fujioka S., Kanno H., Preparation of Phthalic Acid Diamides as Agricultural and Horticultural Insecticides, EP 919542, 1999

[8] Tohnishi M., Nakao H., Kohno E., Nishida T., Furuya T., Shimizu T., Seo A., Sakata K., Fujioka S., Kanno H., Preparation of Phthalamides as Agrohorticultural Insecticides, EP 1006107, 2000

[9] Lahm G. P., Selby T. P., Freudenberger J. H., Stevenson T. M., Myers B. J., Seburyamo G., Smith B. K., Flexner L., Clark C. E., Cordova D., Bioorg. Med. Chem. Lett., 2005, 15, 4898

[10] 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

[11] Lahm G. P., Myers B. J., Selby T. P., Stevenson T. M., Preparation of Insecticidal Anthranilamides, WO 2001070671, 2001

[12] Lahm G. P., Selby T. P., Stevenson T. M., Arthropodicidal Anthranilamides, WO 2003015519, 2003

[13] Tohnishi M., Nishimatsu T., Motoba K., Hirooka T., Akira S., J. Pestic. Sci.(Tokyo, Jpn.), 2010, 35, 490

[14] Lahm G. P., Cordova D., Barry J. D., Bioorg. Med. Chem. Lett., 2009, 17, 4127

[15] Liu P. F., Zhou S., Xiong L. X., Yu S. J., Zhang X., Li Z. M., Chem. J. Chinese Universities, 2012, 33(4), 738

[16] Hughes K. A., Lahm G. P., Selby T. P., Novel Pyrazole-based Anthranilamide Insecticides and Their Preparation, Compositions, and Use, WO 2004046129, 2004

[17] Lahm G. P., Selby T. P., Stevenson T. M., Preparation of Anthranilamide Derivatives for Controlling Invertebrate Pests, WO 2004033468, 2004

[18] Yan T., Yu G. P., Xiong L. X., Yu S. J., Wang S. H., Li Z. M., Chem. J. Chinese Universities, 2011, 32(8), 1750

[19] George P. L., Thomas P. S., Insecticidal Compositions Containing Diamides, WO 2003026415, 2003

[20] Liu P. F., Zhang J. F., Yan T., Xiong L. X., Li Z. M., Chem. Res. Chinese Universities, 2012, 28(3), 430

[21] Luo Y., Yang G., Bioorg. Med. Chem., 2007, 15, 1716

[22] Wang Y., Ou X., Pei H., Lin X., Yu K., Agrochem. Res. Appl., 2006, 10, 20

[23] Busvine J. R., Recommended Methods for Measurement of Pest Resistance to Pesticides, The Food and Agriculture Organization of the United Nations(FAO), Rome, 1980, 21, 3, 119