Synthesis, spectral studies and insect antifeedant activities of some 4-substituted 1-naphthacyl bromide and its esters

Ganesamoorthy Thirunarayanan

Abstract


About nine 4-substituted 1-naphthacyl bromides and its esters have been synthesized by greener synthetic method using fly-ash catalyzed water mediated reaction.  These acyl bromides and esters have been characterized by their physical constants, Mass, IR and NMR spectral data.  These carbonyl frequencies(cm-1) of existed rotomers of these compounds have been assigned and correlated with Hammett substituent constants, F, R and Swain-Lupton’s parameters.  The insect antifeedant activities of the synthesized acyl bromide and esters have been evaluated using 4th instar larvae Achoea Janatha L.


Keywords


4-substituted 1-naphthacylbromides, 4-substituted 1-naphthacylbenzoates, IR& NMR spectra, Correlation analysis, Insect antifeedant activities

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G. Goel, H. P. S. Makkar, G. Francis, K. Becker, Int. J. Toxicol., 26, 279, (2007).

G. Thirunarayanan, P. Mayavel, K. Thirumurthy, Spectrochim. Acta., 91A, 18, (2012).

G. Thirunarayanan, G. Vanangamudi, Arkivoc., 12, 58, (2006).

S. Kajigaeshi, T. Kakinami, T. Okamoto, S. Fujisaki, Bull. Chem. Soc. Jpn., 60, 1159, (1987).

U. Bora, D. Dey, S. Dhar, M. K. Chaudhuri, Pure Appl. Chem., 73, 93, (2001).

M. K. Chaudhuri, A. T. Khan, B. K. Patel, D. Dey, W. Kharmawphlang, T. R. Lakshmiprapha, G. C. Mandal, Tetrahedron Lett. 39, 8163, (1998).

H. Zhao, Z. Song, J. V. Cowins, O. Olubajo, Int. J. Mol. Sci., 9, 33, (2008).

C. T. Chen, Y. S. Munot, J. Org. Chem., 70, 8625, (2005).

J. D. Lou, Z. N. Xu, Tetrahedron Lett., 43, 6149,(2002).

B. Kalluraya, G. Ray, Indian J. Chem., 42(B), 2556, (2003).

G. Thirunarayanan, M. Gopalakrishnan, G. Vanangamudi, Spectrochim. Acta. 67A, 1106, (2007).

F. F. Bamoharram, M. M. Heravi, M. Roshani, M. Jahangir, A. Gharib, J. Mol. Catal., 271A, 126, (2007).

S. Adimurthy, G. Ramachandraiah, A.V. Bedekar, S. Ghosh, B. C. Ranu, P. K. Gosh, Green Chem., 8, 916,(2006).

H. Sharghi, M. Hosseini Sarvari, Tetrahedron., 59, 3627, (2003).

B. D. Paul, C. Dreka, J. L. Summers, M. L. Smith, J. Anal. Toxicol., 20, 506, (1996).

J. Deli, T. Loand, D. Szabo, A. Foldsi, Pharmazie., 39, 539, (1984).

L.Sun, S. Zheng, J. Wang, X. Shen, Indian J. Chem., 41B, 1319, (2002).

M. G. Ahmed, S. A. Ahmed, U. K. R. Romman, T. Sultana, M. A. Hena, S. Kiyooka, Indian J. Chem., 41B, 368, (2002).

L. Q. Wu, C. G. Yang, Y. F. Wu, L. M. Yang, J. Chin. Chem. Soc., 56, 606, (2009).

L. C. King, G. K. Ostrum, J. Org. Chem., 29, 3459, (1964).

P. A. Levene, Org. Synth., II, 88, (1943).

L. A. Yanovskaya, P. A., Terentev, L. N. Belenkii, J. Gen. Chem., 22, 1594, (1952).

F. Krohnke, K. Ellegast, Chem. Ber., 86, 1556 (1953).

E. I. Sanches, M. J. Fumarola, J. Org. Chem., 47,1588, (1982).

A. N. Mayeno, A. J. Curran, R. L. Roberts, C. S. Foote, J. Biol. Chem., 264, 5660 (1989).

D. I. Cajetan, T. Bekele, S. France, J. Wolfer, A. Weatherwax, A. E. Taggi, T. Lectka, J. Org. Chem., 71, 8946, (2006).

R. E. Lovins, L. J. Anrews, R. W. Keef, J. Org. Chem., 28, 2847, (1963).

N. E. Starostenko, N. O. Adeeva, F. N. Zeiberlikh, L. N. Kurkovskaya, N. N. Suvorov, Chem. Heterocycl. Compd., 23, 271, (1987).

S. B. Patwari, M. A. Baseer, Y. B. Vibhute, S. R. Bhusare, Tetrhedron Lett., 44, 4893, (2003).

K. Wakasugi, A. Nakamura, Y. Tanabe, Tetrahedron Lett., 42, 7427, (2001).

D. Taber, J. Am. Chem. Soc., 128, 13052, (2006).

W. J. Yoo, C. J. Li, J. Org. Chem., 71, 6266, (2006).

R. V. H. Jones, W. E. Lindsell, D. D. Palmer, P. N. Preston, A. J. Whitton, Tetrahedron Lett., 46, 8695, (2005).

M. Pittelkow, F.S. Kamounah, U. Boas, B. Pedersen, J. B. Christensen, Synthesis., 2485, (2004)

H. Merima, W. Gunnar, Cellulose., 14, 347, (2007).

Y. Halpern, US Patent No. 5035840, (1991).

R. Moumne, S. Lavielle, P. Karoyan, J. Org. Chem., 71, 3332, (2006).

W.W.Christie, Advances in Lipid Methodology II,(Oily Press, Dundee),(1993), pp.69-111.

P. Ananthakrishna Nadar, C. Gnanasekaran, Indian J. Chem., 14B, 606, (1976).

G. Thirunarayanan, G. Vanangamudi, V. Sathiyendiran, K. Ravi, Indian J. Chem., 50B, 593, (2011).

M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan, J. Thanusu, Catal. Commun., 6, 753, (2005).

M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan, J. Thanusu, R. Govindaraju, Arkivoc., 13, 130, (2006).

M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan, J. Korean Chem. Soc., 51(6), 520, (2007).

A. Perjessy, M. Lacucova, Coll. Czech. Chem. Commun., 36, 2944, (1971).

C. M. Devia, N. B. Pappano, N. B. Debasttista, Rev. Microbiol., 29, 307, (1998).

V. Krishnakumar, R. Ramasamy, Indian J. Pure Appl. Phys., 40, 252, (2002).

A. Sharma, V. P. Gupta, A. Virdi, Indian J. Pure and App. Phys., 40, 246, (2002).

G. K. Dass, Indian J. Chem., 23A, 23, (2001).

P. R. Griffiths, J. M. Chalmers, (2003), Handbook of Vibrational Spectroscopy, (John Wiley & Sons Inc., Chinchester, vol.4, pp.2756.

C. Pellerin, I. Pelletier, Lab International Plus., 19, 10, (2005).

E. T. McBee, D. L. Christman, J. Am. Chem. Soc., 77, 755, (1955).

R. S. Rasmussen, R. R. Brattain, J. Am. Chem. Soc., 71, 1073, (1949).

M. Hauptdchein, C. S. Stokes, E. A. Nodiff, J. Am. Chem. Soc., 74, 4005, (1952).

L. J. Bellamy, R. L. Williams, J. Chem. Soc., 4297, (1957).

J. Shorter, (1973). Correlation analysis in Chemistry: An introduction to linear free energy relationships, Clarendon Press, London.

C. G. Swain, E. C. Lupton, Jr., J. Am. Chem. Soc., 90, 4328, (1968).

M. Mišić-Vuković, M. Radojković-Veličković, J. Serb. Chem. Soc. Rev., 63, 585, (1998)

S. Jovanovic, D. Mijin, M. M. Vuković, Arkivoc., 10, 116, (2006).

P. Ananthakrishna Nadar, C. Gnanasekaran, Indian J. Chem., 17B, 391, (1979).

S. R. Annapoorna, M. Prasad Rao, B. Sethuram, Indian J. Chem., 41A, 1341,(2002).

G. Thirunarayanan, P. Ananthakrishna Nadar, J. Indian Chem. Soc., 83, 1107 (2006).

G. Thirunarayanan, P. Ananthakrishna Nadar, J. Korean Chem. Soc., 50, 183, (2006).

R. Suresh, D. Kamalakkannan, D. Ranganathan, R. Arulkumaran, S.P. Sakthinathan, S. Vijayakumar, K. Sathiyamoorthi, V. Mala, G. Vanangamudi, K. Thirumurthy, P. Mayavel, G. Thirunarayanan, Spectrochim. Acta. 101A, 239, (2013).

G. Thirunarayanan, Indian J. Chem., 46B, 1511, (2007).

P. Janaki, K. G. Sekar, G. Thirunarayanan, J. Saudi Chem. Soc., 20, 58, (2016).

M. C. Unlusoy, N. Altanlar, R. Ertan, Turk. J. Chem., 29, 187, (2005).

B. Ahilstrom, M. C. Bertillson, R. A. Thompson, Antimicrob. Agents Chemother., 39, 50, (1995).

A. A. Williams, E. W. Sugandhi, R. V. Macri, J. O. Falkinham, R. D. Gandour, J. Antimicrob. Chemother., 59, 451, (2007).

O. E. Nwfor, M. J. Ikenebomeh, African J. Biotechnol., 8, 2843, (2009).

W. B. Wan, J. R. Beadle, C. Hartline, E. R., Kern, S. L. Ciesla, N. Valiaeva, K. Y. Hostetler, Antimicrob Agents Chemother., 49, 656, (2005).

B. C. Brasileiro, V. R. Pizziolo, D. S. Raslan, C. M. Jamal, D. Silveira, Brazilian J. Pharm. Sci., 42, 195, (2006).

A. Konopka, T. Zakharova, M. Bischoff, L. Oliver, C. Nakatsu, R. F. Turco, Appl. Environ. Micorbiol., 65, 3356, (1999).

S. Y. Liu, F. Sporer, M. Wink, J. Jourdane, R. Henning, Y. L. Li, A. Ruppel, Trop. Med. Int. Health., 2179, (1997).

G. Thirunarayanan, J. Indian Chem. Soc., 85, 447, (2008).

G. Thirunarayanan, S. Surya, S. Srinivasan, G. Vanangamudi, V. Sathiyendiran, Spectrochim. Acta., 75A, 152, (2010).

V. G. Dethler, (1947). Chemical insect attractants and repellants, Philadeciphia, p. 210.




DOI: http://dx.doi.org/10.17951/aa.2016.71.2.67
Date of publication: 2017-04-03 12:28:05
Date of submission: 2016-06-22 18:40:36


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