Abstract
A series of anthranilic diamides with a hydrazone substructure was synthesised and characterised using 1HNMR, 13C NMR, IR and elemental analyses. The in vitro insecticidal activity of all the compounds was tested against Plutella xylostella. The results showed the synthesised compounds to possess good insecticidal activity. The LC50 values of compounds VIIg, VIIl, VIIm, VIIn exhibited excellent insecticidal activities, with the LC50 affording 7.92 mg L−1, 12.01 mg L−1, 0.62 mg L−1 and 10.71 mg L−1, respectively. These may prove to be useful as potential insecticidal agents.
Similar content being viewed by others
References
Aggarwal, N., Kumar, R., Srivastva, C., Dureja, P., & Khurana, J. M. (2010). Synthesis of nalidixic acid based hydrazones as novel pesticides. Journal of Agricultural and Food Chemistry, 58 3056–3061. DOI: 10.1021/jf904144e.
Böger, M., Dürr, D., Gsell, L., Hall, R. G., Karrer, F., Kristiansen, O., Maienfisch, P., Pascual, A., & Rindlisbacher, A. (2001). Synthesis and structure-activity relationships of benzophenone hydrazone derivatives with insecticidal activity. Pest Management Science, 57 191–202. DOI: 10.1002/1526-4998(200102)57:2<191::aid-ps275>3.0.co;2-o.
Chen, Y. B., Li, J. L., Shao, X. S., Xu, X. Y., & Li, Z. (2013). Design, synthesis and insecticidal activity of novel anthranilic diamides with benzyl sulfide scaffold. Chinese Chemical Letters, 24 673–676. DOI: 10.1016/j.cclet.2013.04.047.
Clark, D. A., Lahm, G. P., Smith, B. K., Barry, J. D., & Clagg, D. G. (2008). Synthesis of insecticidal fluorinated anthranilic diamides. Bioorganic & Medicinal Chemistry, 16 3163–3170. DOI: 10.1016/j.bmc.2007.12.017.
Feng, Q., Liu, Z. L., Xiong, L. X., Wang, M. Z., Li, Y. Q., & Li, Z. M. (2010). Synthesis and insecticidal activities of novel anthranilic diamides containing modified N-pyridylpyrazoles. Journal of Agricultural and Food Chemistry, 58 12327–12336. DOI: 10.1021/jf102842r.
Feng, Q., Yu, G. P., Xiong, L. X., Wang, M. Z., & Li, Z. M. (2011). Synthesis and insecticidal evaluation of novel n-pyridylpyrazolecarboxamides containing different substituents in the ortho-position. Chinese Journal of Chemistry, 29 1651–1655. DOI: 10.1002/cjoc.201180295.
Furlong, M. J., Wright, D. J., & Dosdall, L. M. (2013). Diamondback moth ecology and management: problems, progress, and prospects. Annual Review of Entomology, 58 517–541. DOI: 10.1146/annurev-ento-120811-153605.
Hasanshahi, G., Abbasipour, H., Askarianzadeh, A., Karimi, J., & Jahan, F. (2013). Seasonal population fluctuations of the diamondback moth, Plutella xylostella (L.) (Lep.: Plutellidae) on different cauliflower cultivars. Archives of Phytopathology and Plant Protection, 46 1136–1149. DOI: 10.1080/03235408.2012.760897.
Hollingshaus, J. G. (1987). Inhibition of mitochondrial electron transport by hydramethylnon: A new amidinohydrazone insecticide. Pesticide Biochemistry & Physiology, 27 61–70. DOI: 10.1016/0048-3575(87)90096-4.
Ikegami, H., Jachmann, M., Nokura, Y., & Iwata, C. (2007). W.O. Patent No. 2007043677. Geneva, Switzerland:World Intellectual Property Organization.
Ikegami, H., Jachmann, M., & Nokura, Y. (2008a). W.O. Patent No. 2008126889. Geneva, Switzerland:World Intellectual Property Organization.
Ikegami, H., Jachmann, M., & Nokura, Y. (2008b). W.O. Patent No. 2008126890. Geneva, Switzerland:World Intellectual Property Organization.
Klein, C. D., & Oloumi, H. (2005). Metaflumizone: a new insecticide for urban insect control from BASF, In C. Y. Lee, & W. H. Robinson, (Eds.) Proceedings of the fifth international conference on urban pests (pp. 101–105). Penang, Malaysia: Perniagaan Ph,ng @ P&Y Design Network.
Koyanagi, T., Yokeda, T., Higuchi, K., Kiriyama, K., Taguchi, Y., & Hamamoto, T. (2006). W.O. Patent No. 200,608,031,1. Geneva, Switzerland: World Intellectual Property Organization.
Lahm, G. P., Selby, T. P., & Stevenson, T. M. (2006). W.O. Patent No. 2006055922. Geneva, Switzerland: World Intellectual Property Organization.
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. (2007). Rynaxypyr™:A new insecticidal anthranilic diamide that acts as a potent and selective ryanodine receptor activator. Bioorganic & Medicinal Chemistry Letters, 17 6274–6279. DOI: 10.1016/j.bmcl.2007.09.012.
Lahm, G. P., Cordova, D., & Barry, J. D. (2009). New and selective ryanodine receptor activators for insect control. Bioorganic & Medicinal Chemistry, 17 4127–4133. DOI: 10.1016/j.bmc.2009.01.018.
Li, W. Q., Zhang, Z. J., Nan, X., Liu, Y. Q., Hu, G. F., Yu, H. T., Zhao, X. B., Wu, D., & Yan, L. T. (2014). Design, synthesis and bioactivity evaluation of novel benzophenone hydrazone derivatives. Pest Management Science, 70 667–673. DOI: 10.1002/ps.3607.
Liu, C. D., Xia, X. J., Yu, L. J., Xing, J. H., Chen, J., & Peng, W. L. (2007). Synthesis and biological activity of N′-substituted-4-halogenated-N-methyl-4-methanesulfanilamide benzophennonehydrazone derivatives. Agrochemicals, 46 97–99. DOI: 10.3969/j.issn.1006-0413.2007.02.008. (in Chinese)
Liu, M., Wang, Y., Wangyang, W. Z., Liu, F., Cui, Y. L., Duan, Y. S., Wang, M., Liu, S. Z., & Rui, C. H. (2010a). Design, synthesis, and insecticidal activities of phthalamides containing a hydrazone substructure. Journal of Agricultural and Food Chemistry, 58 6858–6863. DOI: 10.1021/jf1000919.
Liu, Y. B., Peng, W. L., Yu, L. J., Xing, J. H., Chen, J., Xia, X. J., & Shen D. L. (2010b). Synthesis and biological activity of benzophennonehydrazone derivatives containing semicarbazone structure. Agrochemicals, 49 407–409. DOI: 10.3969/j.issn.1006-0413.2010.06.004. (in Chinese)
Oerke, E. C. (2006). Crop losses to pests. Journal of Agricultural Science, 144 31–43. DOI: 10.1017/s0021859605005708.
Selby, T. P., Lahm, G. P., Stevenson, T. M., Hughes, K. A., Cordova, D., Annan, I. B., Barry, J. D., Benner, E. A., Currie, M. J., & Pahutski, T. F. (2013). Discovery of cyantranilip-role, a potent and selective anthranilic diamide ryanodine receptor activator with cross-spectrum insecticidal activity. Bioorganic & Medicinal Chemistry Letters, 23 6341–6345. DOI: 10.1016/j.bmcl.2013.09.076.
Seo, A., Tohnishi, M., Nakao, H., Furuya, T., Kodama, H., Tsubata, K., Fujioka, S., Kodama, H., Nishimatsu, T., & Hirooka, T. (2007). Flubendiamide, a new insecticide characterized by its novel chemistry and biology. In H. Ohkawa, H. Miyagawa, & P. W. Lee (Eds.), Pesticide chemistry (pp. 127–135). Weinheim, Germany: Wiley.
Tabanca, N., Ali, A., Bernier, U. R., Khan, I. A., Kocyigit-Kaymakcioglu, B., Oruç-Emre, E. E., Unsalan, S., & Rollas, S. (2013). Biting deterrence and insecticidal activity of hydrazide-hydrazones and their corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles against Aedes aegypti. Pest Management Science, 69 703–708. DOI: 10.1002/ps.3424.
Takagi, K., Ohtani, T., Nishida, T., Hamaguchi, H., Nishimatsu, T., & Kanaoka, A. (1992). E.P. Patent No. 462456. Munich, Germany: European Patent Office.
Tohnishi, M., Nakao, H., Kohno, E., Nishida, T., Furuya, T., Shimizu, T., Seo, A., Sakata, K., Fujioka, S., & Kanno, H. (2000). E.P. Patent No. 1006107. Munich, Germany: European Patent Office.
Tohnishi, M., Nakao, H., Fumya, T., Seo, A., Kodama, H., Tsubata, K., Fujioka, S., Kodama, H., Hirooka, T., & Nishimatsu, T. (2005). Flubendiamide, a novel insecticide highly active against lepidoptemus insect pests. Journal of Pesticide Science, 30 354–360. DOI: 10.1584/jpestics.30.354.
Wang, F., Cao, J., Yuan, L. P., Guo, Q. M., Ni, C. C., Shen, Z., & Zhang, Y. B. (2006). Synthesis and bioactivity of a series of novel hydrazone derivatives. Chinese Journal of Pesticide Science, 8 176–179. DOI: 10.3321/j.issn:1008-7303.2006.02.017. (in Chinese)
Wu, J., Song, B. A., Hu, D. Y., Yue, M., & Yang, S. (2012). Design, synthesis and insecticidal activities of novel pyrazole amides containing hydrazone substructures. Pest Management Science, 68 801–810. DOI: 10.1002/ps.2329.
Wu, J., Bai, S., Yue, M., Luo, L. J., Shi, Q. C., Ma, J., Du, X. L., Kang, S. H., Hu, D., & Yang, S. (2014). Synthesis and insecticidal activity of 6,8-dichloro-quinazoline derivatives containing a sulfide substructure. Chemical Papers, 68 969–975. DOI: 10.2478/s11696-014-0540-z.
Yackman, M., & Sanemitsu, M. (2007). J.P. Patent No. 2007077106. Tokyo, Japan: Japan Patent Office.
Yasuyuki, K., Takeshi, K., & Tokio, T. (2005). J.P. Patent No. 2005272304. Tokyo, Japan: Japan Patent Office.
Zhang, J. F., Xu, J. Y., Wang, B. L., Li, Y. X., Xiong, L.X., Li, Y. Q., Ma, Y., & Li, Z. M. (2012). Synthesis and insecticidal activities of novel anthranilic diamides containing acylthiourea and acylurea. Journal of Agricultural and Food Chemistry, 60 7565–7572. DOI: 10.1021/jf302446c.
Zhang, X. L., Li, Y. X., Ma, J. L., Zhu, H. W., Wang, B. L., Mao, M. L., Xiong, L. X., Li, Y. Q., & Li, Z. M. (2014). Synthesis and insecticidal evaluation of novel anthranilic diamides containing N-substitued nitrophenylpyrazole. Bioorganic & Medicinal Chemistry, 22 186–193. DOI: 10.1016/j.bmc.2013.11.038.
Zhao, Y., Xu, L. P., Tong, J., Li, Y. Q., Xiong, L. X., Li, F., Peng, L. N., & Li, Z. M. (2012). Synthesis, crystal structure and biological activity of novel anthranilic diamide insecticide containing alkyl ether group. Molecular Diversity, 16 711–725. DOI: 10.1007/s11030-012-9406-x.
Zhou, S., Jia, Z. H., Xiong, L. X., Yan, T., Yang, N., Wu, G. P., Song, H. B., & Li, Z. M. (2014). Chiral dicarboxamide scaffolds containing a sulfiliminyl moiety as potential ryanodine receptor activators. Journal of Agricultural and Food Chemistry, 62 6269–6277. DOI: 10.1021/jf501727k.
Author information
Authors and Affiliations
Corresponding author
Additional information
The first and the second authors contributed equally to this work.
Rights and permissions
About this article
Cite this article
Wu, J., Xie, DD., Shan, WL. et al. Synthesis and insecticidal activity of anthranilic diamides with hydrazone substructure. Chem. Pap. 69, 993–1003 (2015). https://doi.org/10.1515/chempap-2015-0100
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1515/chempap-2015-0100