Abstract
This paper describes the synthesis of a series of quinolines graphted with hydrazones, pyrazoles, pyridazine, phthalazine, triazepinone, semicarbazide, and thiomorpholide moieties and four metal complexes. These derivatives were screened against Fusarium oxysporum and the red palm weevil (RPW) Rhynchophorus ferrugineus Oliver (coleopteran: Curculionidae) as palm pathogens. Only chlorinated quinolines were active against these organisms with hydrazones being good fungicides, while those modified with pyrazoles and pyrazines showed moderate insecticidal activity. A unique trihydroxylated hydrazone was active against both organisms, while another hydrazone, the most potent fungicide in this series, exhibited insecticidal activity only upon complexation with Zn2+ ions.
Similar content being viewed by others
References
Murphy, S.T. and Briscoe, B.R., Biocontrol News and Information, 1999, vol. 20, no. 1, pp. 35N–46N.
Saremi, H., Okhovvat, S.M., and Ashrafi, S.J., Commun. Agric. Appl. Biol. Sci., 2007, vol. 72, no. 4, pp. 831–837.
Ferry, M. and Gomez, S., Palms, 2002, vol. 46, no. 4, pp. 172–178.
Monzer, M.A. and Hesham, A.S., Egypt. Acad. J. Biolog. Sci., 2009, vol. 2, no. 1, pp. 47–53.
Longley, N., Muzoora, C., Taseera, K., Mwesigye, J., Rwebembera, J., Chakera, A., Wall, E., Andia, I., Jaffar, S., and Harrison, T.S., Clinical Infectious Diseases, 2008, vol. 47, no. 12, pp. 1556–1561.
Muller, F., Agrochemicals: Composition, Production, Toxicity, Applications, Toronto: Wiley-VCH, 2000.
Wu, J., Song, B.A., Hu, D.Y., Yue, M., and Yang, S., Pest Manag. Sci., 2012, vol. 68, pp. 801–810.
Al Jabr, A., and Abo-El-Saad, M., Am. J. Environ. Sci., 2008, vol. 4, no. 6, pp. 595–601.
Aly, M.R.E., Abd El-Mageed, A.E.M., El-Kafafy, A.M.A., and Nawwar, G.A., J. Plant Prot. Res., 2011, vol. 51, no. 2, pp. 114–120.
Krafts, K., Hempelmann, E., and Skorska-Stania, A., Parasitol. Res., 2012, no. 1, pp. 1–6.
Boschelli, D.H. and Wu, B., Ye. F., Durutlic, H., Golas, J. M., Lucas, J., and Boschelli, F., Bioorg. Med. Chem., 2008, vol. 16, pp. 405–412.
Zhang, H.Z., Claassen, G., Crogran-Grundly, C., Tseng, B., Drewe, J., and Cai, S.X., Bioorg. Med. Chem., 2008, vol. 16, pp. 222–231.
Hollingshaus, J.G., Pestic. Biochem. Physiol., 1987, vol. 27, pp. 61–70.
Klein, C.D. and Oloumi, H., in Proceedings of the 5th International Conference on Urban Pests, Lee, C.Y., and Robinson, W.H., Eds., Perniagan Ph’ng, P&Y Design Network, Malaysia, 2005, p. 101.
Dai, H., Yu, H.-B., Liu, J.-B., Li, Y.-Q., Qin, X., Zhang, X., Qin, Z.-F., Wang, T.-T., and Fang, J.-X., Arkivoc, 2009, vol. II, pp. 126–142.
Dong, W.-L., Xu, J.-Y., Xiong, L.-X., and Li, Z.-M., Molecules, 2012, vol. 17, pp. 10414–10428.
Savini, L., Chiasserini, L., Gaeta, A., and Pellerano, C., Bioorg. Med. Chem., 2002, vol. 10, pp. 2193–2198.
Hasanen, J.A., Ibrahim, E.I., Orabi, A.S., Youssef, M.F., and Oriental, J., Chem., 2007, vol. 23, pp. 27–33.
Lubenets, V.I., Stadnitskaya, N.E., and Novikov, V.P., Russ. J. Org. Chem., 2000, vol. 36, no. 6, pp. 851–853.
Chi-Hoon, L., Ju-Hyun, J., Sang-Guei, L., and HoiSeon, L., J. Korean Soc. Appl. Biol. Chem., 2010, vol. 53, no. 4, pp. 464–469.
Aly, M.R.E., El Shahed, F.A., Soliman, H.A., Ibrahim, E.I., Ibrahim, Z.S., and El-Shazly, S.A.M., Russ. J. Bioorg. Chem., 2012, vol. 38, no. 4, pp. 428–434.
Girolami, G.S., Rauchfuss, T.B., and Angelici, R.J., Synthesis and Technique in Inorganic Chemistry, 3rd ed., Sausalito: University Science Books, 1999.
Chiswell, B., Crawford, J.P., and O’reilly, E.J., Inorg. Chim. Acta, 1980, vol. 40, pp. 223–228.
Maurya, M.R., Antony, D.C., Gopinathan, S., Puranik, V.G., Tavale, S.S., Gopinathan, C., and Maurya, R.C., Bull. Chem. Soc. Jpn., 1995, vol. 68, pp. 2847–2852.
Silverstein, R.M., Bassler, G.C., and Morrill, T.C., Spectroscopic Identification of Organic Compounds, 5th ed., New York, NY, USA: John Wiley and Sons, 1991.
Mishra, A.P. and Pandey, L.R., Indian J. Chem. A, 2005, vol. 44, pp. 1800–1805.
Nakamoto, K., Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part A and Part B, New York, NY, USA: John Wiley and Sons, 1998.
Selbin, J., Chem. Rev., 1965, vol. 65, pp. 153–175.
Maurya, R.C. and Rajput, S., J. Mol. Str., 2006, vol. 794, pp. 24–34.
Ibrahim, M.M., Mersal, G.A.M., El-Shazly, S.A., and Ramadan, A.M., Int. J. Electrochem. Sci., 2012, vol. 7, pp. 7526–7546.
Aranha, P.E., Do Santo, M.P., Romera, S., and Dockal, E. R., Polyhedron, 2007, vol. 26, pp. 1373–1382.
Abbott, W.S., J. Econ. Entomol., 1925, vol. 18, no. 2, pp. 265–267.
Finney, D.J., Probit Analysis. A Statistical Treatment of the Sigmoid Response Curve, 7th ed., Cambridge, England: Cambridge Univ. Press, 1971.
Sun, Y.P., J. Econ. Entomol., 1950, vol. 43, no. 1, pp. 45–60.
Broum, D.F. and Sinclair, J.B., Phytopath., 1968, vol. 58, pp. 976–980.
Author information
Authors and Affiliations
Corresponding author
Additional information
The article is published in the original.
Rights and permissions
About this article
Cite this article
Aly, M.R.E., Ibrahim, M.M., Okael, A.M. et al. Synthesis, insecticidal, and fungicidal screening of some new quinoline derivatives. Russ J Bioorg Chem 40, 214–227 (2014). https://doi.org/10.1134/S1068162014020022
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1068162014020022