Synthesis, characterization and spectral studies of various newer long chain aliphatic acid (2-hydroxy benzylidene and 1H-indol-3-ylmethylene) hydrazides as mosquito para-pheromones

  • Awasthi, Suman ;
  • Rishishwar, Poonam ;
  • Rao, Ambati N. ;
  • Ganesan, Kumaran ;
  • Malhotra, Ramesh Chandra
  • Published : 2007.12.20


Various long chain aliphatic acid hydrazides react with aromatic and heterocyclic aldehydes in alcoholic medium in refluxing conditions to give corresponding 2-hydroxy benzylidene and 1H-indol-3-ylmethylene hydrazides, a newer class of mosquito para-pheromones. We describe here synthesis of various novel long chain aliphatic acid (2- hydroxy benzylidene and 1H-indol-3-ylmethylene) hydrazides by conventional as well as microwave irradiation techniques. The structures of these compounds have been confirmed by spectroscopic techniques (FTIR, NMR & MS). Some of the interesting features of the electron impact mass spectral fragmentation pattern of these compounds have also been discussed.


Long Chain Aliphatic Acid Hydrazide;Long Chain Aliphatic Acid (2-hydroxy benzylidene & 1H-indol-3-ylmethylene) Hydrazide;Mosquito Para-pheromones;Microwave


  1. Bonicke, R.; Krach, J. Z. Hyg Infektionakranch 1954, 139, 140
  2. Haksar, C. N.; Malhotra, R. C.; Pandya G.; Sethi, R. K. Lab. J. Sc. Technol., 1981, 9B, 34
  3. Binon, F.; Royer, R. J. Chem. Soc., 1953, 1358
  4. Zikolova, Sv. Farmatoiya, 1965, 15(4), 185
  5. Roman, K. L. Span. Patent, ES 506,945, 1982
  6. Dhadialla, T. S.; Carlson, G. R.; Le, D. P. Annual Review of Entomology 1998, 43, 545-569
  7. Banik, B. K.; Barakat, K. J.; Wagle, W. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem., 1999, 64, 5746
  8. Mendki, M. J.; Ganesan, K.; Prakash, S.; Suryanarayana, M. V. S.; Malhotra, R. C.; Rao, K. M.; Vaidyanathaswamy, R. Current Science, 2000, 78, 1295-1296
  9. Bentley, M. D.; McDaniel, I. N.; Yatagai, M.; Lee, H. P.; Maynard, R. Environmental Entomology, 1979, 8, 206-209
  10. Knight, J. C.; Corbet, S. A. Journal of American Mosquito Control Association, 1991, 7, 37-41
  11. Villemine, D.; Martin, B. J. Chem. Res., 1994, 146
  12. Lu, Y. F.; Fallis, A. G. Can. J. Chem., 1995, 73, 2239
  13. Soriente, A.; Spinella, A.; DeRosa, M.; Giordano, M.; Seettri, A. Tetrahedron Lett, 1997, 38, 289
  14. Suarez, M.; Loupy, A.; Salfran, E.; Moran, L.; Rolando, E. Heterocycles, 1999, 51, 21
  15. Goncalo, P.; Roussel, C.; Melot, J. M.; Vebrel, J. J. Chem. Soc. Perkin Trans 2, 1999, 2111
  16. Danks, T. N. Tetrahedron Lett, 1999, 40, 3957
  17. Verma, R. S. Green Chemistry, 1999, 1, 43
  18. Rishiswar, P.; Awasthi, S.; Jain, N.; Prakash, S.; Ganesan, K.; Malhotra, R.C.; Vijayaraghavan, R. Ovipositional responses of Aedes aegypti (Diptera: Culicidae) to novel synthesized long chain aliphatic hydrazides (to be communicated to Vector Ecology)
  19. Ganesan K.; Mendki, M. J.; Suryanarayana, M. V. S.; Prakash, S.; Malhotra, R. C. Australian Journal of Entomology, 2000, 45, 75-80
  20. Roman, K. L. Chem. Abstr., 1985, 89, 67124

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