Design, Synthesis and Insecticidal Activity of Novel Anthranilic Diamides Containing Oxime Ester and Diacylhydrazine Moieties

doi:10.1007/s40242-014-3408-4

Abstract

Abstract:

Two series of novel anthranilic diamides containing oxime ester and diacylhydrazine moieties were designed and synthesized. Their structures were characterized by melting points, ¹H NMR, ¹³C NMR and high resolution mass spectrometry(HRMS). The single crystal structure of compound 7e was determined by X-ray diffraction and their evaluated insecticidal activity against oriental armyworm(Mythimna separata) indicates that some of the compounds exhibited moderate insecticidal activities. Among the 20 compounds, 6a and 6b show 100% larvicidal activity against Mythimna separate Walker at the test concentration of 100 mg/L.

Key words: Anthranilic diamide, Oxime ester, Diacylhydrazine, Insecticidal activity

LIU Chen, ZHANG Jifeng, ZHOU Yunyun, WANG Baolei, XIONG Lixia, LI Zhengming. Design, Synthesis and Insecticidal Activity of Novel Anthranilic Diamides Containing Oxime Ester and Diacylhydrazine Moieties[J]. Chemical Research in Chinese Universities, 2014, 30(2): 228-234.

References

[1] Ohkawa H., Miyagawa H., Lee P. W., Pesticide Chemistry, Crop Protection, Public Health, Environmental Safety, 2008, Chapter 13, 127
[2] Kämer W., Schirmer U., Jeschke P., Witschel M., Modern Crop Protection Compounds, Vol. 3, 2nd Edition, Wiley-VCH, Weinheim, 2012, 1121
[3] Lahm G. P., Selby T. P., Frendenberger 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
[4] Lahm G. P., Cordova D., Barry J. D., Bioorg. Med. Chem., 2009, 17, 4127
[5] Lahm G. P., Stevenson T. M., Selby T. P., Frendenberger J. H., Cordova D., Flexner L., Bellin C. A., Dubas C. M., Smith B. K., Hughes K. A., Hollingshaus G., Clark C. E., Benner E. A., Bioorg. Med. Chem. Lett., 2007, 17, 6274
[6] Clark D. A., Lahm G. P., Smith B. K., Barry J. D., Clagg D. G., Bioorg. Med. Chem., 2008, 16, 3163
[7] Alig B., Fischer R., Funke C., Gesing E. F., Hense A., Malsam O., Drewes M. W., Gorgens U., Murata T., Wada K., Arnold C., Sanwald E., Anthranilic Acid Diamide Derivative with Hetero-aromatic and Hetero-cyclic Substituents, WO 2007144100, 2007
[8] Alig B., Fischer R., Funke C., Gesing R. E. F., Hense A., Kruger B. W., Losel P., Arnold C., Anthranilamides, WO 2006000336, 2006
[9] 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
[10] Liu P. F., Zhang J. F., Yan T., Xiong L. X., Li Z. M., Chem. Res. Chinese Universities, 2012, 28(3), 430
[11] Kruger B., Hense A., Alig B., Fischer R., Funke C., Gesing E. R., Malsam A., Drewes M. W., Arnold C., Lummen P., Sanwald E., Dioxazine-and Oxadiazine-substituted Arylamides, WO 2007031213, 2007
[12] Muehlebach M., Craig G. W., N-Cyanoalkylanthranilamides As Insecticides, WO 2008064891, 2008
[13] Wu J., Song B. A., Hu D. Y., Yue M., Yang S., Pest Manag. Sci., 2012, 68, 801
[14] Feng Q., Yu G. P., Xiong L., X., Wang M. Z., Li Z., M., Chin. J. Chem., 2011, 29, 1651
[15] Loiseleur O., Hall R. G., Stoller A. D., Graig G. W., Jeanguenat A., Edmunds A., Novel Insecticides, WO 2009024341, 2009
[16] Loiseleur O., Durieux P., Trah S., Edmunds A., Jeanguenat A., Stoller A., Hughes D. J., Pesticides Containing a Bicyclic Bisamide Structure, WO 2007093402, 2007
[17] Mao M. Z., Li Y. X., Liu Q. X., Zhou Y. Y., Zhang X. L., Xiong L. X., Li Y. Q., Li Z. M., Bioorg. Med. Chem. Lett., 2013, 23, 42
[18] Finkelstein B. L., Lahm G. P., Selby T. P., Stevenson T. M., Ortho-substituted Aryl Amides for Controlling Invertebrate Pests, WO 03016300, 2003
[19] Kang Z., Lei D. W., Wang J. F., Yang H. W., Sun B. X., Zhang H., Li B., Pyrazolylimine Compounds and the Use Thereof, CN 101863874, 2010
[20] 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
[21] Wang B. L., Ma Y., Xiong L. X., Li Z. M., Chin. J. Chem., 2012, 30, 815
[22] Dong W. L., Xu J. Y., Xiong L. X., Liu X. H., Li Z. M., Chin. J. Chem., 2009, 327, 579
[23] Swada Y., Yanai T., Nakagawa H., Tsukamoto Y., Yokoi S., Yanagi M., Toya T., Sugizaki H., Kato Y., Shirakura H., Watanabe T., Yajima Y., Kodama S., Masui A., Pest Manag. Sci., 2002, 59, 36
[24] Abbott, W. S., J. Econ. Entomol., 1925, 18, 265