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Pyriproxyfen cyclodextrin inclusion compounds

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Abstract

Pyriproxyfen is a pyridine based pesticide which is effective against mosquito larvae. Here we report the inclusion complexes (ICs) between guest pyriproxyfen and host β and γ cyclodextrins, but not with α cyclodextrin, based on WAXD, DSC, FTIR, and TGA characterization results. We show that one pyriproxyfen molecule is covered with between one and two β or γ cyclodextrin molecules when it forms columnar ICs upon precipitation from aqueous solution.

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References

  1. Szejtli, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743–1754 (1998)

    Article  CAS  Google Scholar 

  2. Guieu, S., Sollogoub, M.: Advances in cyclodextrin chemistry. In: Werz, D.B., Vidal, S. (eds.) Modern Synthetic Methods in Carbohydrate Chemistry: From Monosaccharides to Complex Glycoconjugates. Wiley-VCH Verlag GmbH & Co KGaA, Weinheim (2013)

  3. El-Nokaly, M.A., David, M.P., Charpentier, B.A.: Polymeric Delivery Systems. American Chemical Society, Washington, DC (1993)

  4. Bajpai, M., Gupta, P., Bajpai, S.K.: Silver(I) ions loaded cyclodextrin-grafted-cotton fabric with excellent antimicrobial property. Fibers Polym. 11(1), 8–13 (2009)

    Article  Google Scholar 

  5. Rusa, C.C., Bridges, C., Ha, S., Tonelli, A.E.: Conformational changes induced in bombyx mori silk fibroin by cyclodextrin inclusion complexation. Macromolecules 38, 5640–5646 (2005)

  6. Uyar, T., El-Shafei, A., Wang, X., Hacaloglu, J., Tonelli, A.E.: The solid channel structure inclusion complex formed between guest styrene and host gamma cyclodextrin. J. Incl. Phenom. Macro. 55, 109–121 (2006)

  7. Suzuki, M., Tsutsui, M., Ohmori, H.: 2H NMR study of the self-assembly of an azo dye-cyclomaltooctaose (γ-cyclodextrin) complex. Carbohyd. Res. 261, 223–230 (1990)

  8. Rusa, C.C., Rusa, M., Peet, J., Uyar, T., Fox, J., Hunt, M., Wang, X., Balik, C., Tonelli, A.E.: The nano-threading of polymers. J. Incl. Phenom. Macro. 55, 185–192 (2006)

  9. Wei, M., Tonelli, A.E.: Compatiblization of polymers via coalescence from their common cyclodextrin inclusion compounds. Macromolecules 34, 4061–4065 (2001)

  10. Martínez, G., Gómez, M.A., Villar-Rodil, S., Garrido, L., Tonelli, A.E., Balik, C.: Formation of crystalline inclusion compounds of poly (vinly chloride) of different stereoregularity with γ-cyclodextrin. J. Polym. Sci. Pol. Chem. 45, 2503–2513 (2007)

  11. Rusa, C.C., Shuai, X., Shin, I.D., Bullions, T.A., Wei, M., Porbeni, F.E., Lu, J., Huang, L., Fox, J., Tonelli, A.E.: Controlling the behaviors of biodegradable/bioabsorbable polymers with cyclodextrins. J. Polym. Environ. 12, 157–163 (2004)

  12. Mohan, A., Gurarslan, A., Joyner, X., Child, R., Tonelli, A.E.: Melt-crystallized nylon-6 nucleated by the constrained chains of its non-stoichiometric cyclodextrin inclusion compounds and the nylon-6 coalesced from them. Polymer 52, 1055–1062 (2011)

  13. Gurarslan, A., Joijode, A.S., Tonelli, A.E.: Polymers coalesced from their cyclodextrin inclusion complexes: What can they tell us about the morphology of melt‐crystallized polymers? J. Polym. Sci., Part B: Polym. Phys. 50(12), 813–823 (2012)

  14. World Health Organization specifications and evaluations for public health pesticides. Pyriproxyfen, pp. 1–19

  15. Sullivan, J.: Environmental Fate of Pyriproxyfen. Environmental Monitoring and Pest Management Branch Department of Pesticide Regulation. Sacramento (2000)

  16. Kumar, A.R., Ashok, K., Brahmaiah, B., Nama, S., Baburao, C.: The cyclodextrins: A review. Int. J. Pharm. Res. Biosci. 2(2), 291–304 (2013)

  17. Hees, T.V., Piel, G., Evrard, B., Otte, X., Thunus, L., Delattre, L.: Application of supercritical carbon dioxide for the preparation of a piraxicam-β-cyclodexrin inclusion compound. Pharm. Res. 16, 1864–1870 (1999)

  18. Iliescu, T., Baia, M., Miclaus, V.: A raman spectroscopic study of the diclofenac sodium-β-cyclodextrin interaction. Eur. J. Pharm. Sci. 22, 487–495 (2004)

  19. Whang, H.S., Hunt, M.A., Wrench, N., Hockney, J.E., Farin, C.E., Tonelli, A.E.: Nonoxynol-9-α-cyclodextrin inclusion compound and its application for the controlled release of nonoxynol-9 spermicide. J. App. Polym. Sci. 106, 4107–4109 (2007)

  20. Invest, J.F., Lucas, J.R.: Pyriproxyfen as a mosquito larvicide. In: Robinson, W.H., Bajomi, D. (eds.) Proceedings of the Sixth International Conference on Urban Pests, 2008. OOK-Press KFT, Veszprem

  21. Huang, L., Tonelli, A.E.: Polymer inlusion compounds. Rev. Macromol. Chem. Phys. 38(4), 781–837 (1998)

  22. Rusa, C.C., Rusa, M., Gomez, M., Shin, I.D., Fox, J.D., Tonelli, A.E.: Nanostructuring high molecular weight isotactic polyolefins via processing with γ-cyclodextrin inclusion compounds. Formation and characterization of polyolefin-γ-cyclodextrin inclusion compounds. Macromolecules 37, 7992–7999 (2004)

  23. Takeo, K., Kuge, T.: Complexes of starchy materials with organic compounds part IV X-ray diffraction of γ-cyclodextrin complexes. Agric. Biol. Chem. 34(4), 568–574 (1970)

  24. Caira, M.R.: On the isostructurality of cyclodextrin inclusion complexes and its practical utility. Rev. Roum. Chim. 46(4), 371–386 (2001)

  25. Topchieva, I.N., Panova, I.G., Kurganov, B.I., Spiridonov, V.V., Mayukhina, E.V., Filippov, S.K., Lezov, A.V.: Noncovalent columnar structures based on β-cyclo-dextrin. Colloid J. 70(3), 356–365 (2008)

  26. Huang, L., Allen, E., Tonelli, A.E.: Inclusion compounds formed between cyclodextrins and nylon 6. Polymer 40, 3211–3221 (1999)

  27. Lindner, K., Saenger, W.: Crystal and molecular structure of cyclohepta amylose dodecahydrate. Carbohydr. Res. 99(2), 103–115 (1982)

  28. Stezowski, J.J., et al.: Dimeric beta-cyclodextrin complexes may mimic membrane diffusion transport. Nature 274(5671), 617–619 (1978)

  29. Huang, L., et al.: Formation of a flame retardant-cyclodextrin inclusion compound and its application as a flame retardant for poly (ethylene terephthalate). Polym. Degrad. Stab. 71(2), 279–284 (2001)

  30. Louiz, S., Labiadh, H., Abderrahim, R.: Synthesis and spectroscopy studies of the inclusion complex of 3-amino-5-methyl pyrazole with beta-cyclodextrin. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 134, 276–282 (2015)

  31. Alig, B., Stendel, W., Londershausen, M.: US Patent US5057527A (1991)

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Acknowledgments

We are grateful to Dr. Charles Apperson for providing the pyriproxyfen.

Conflict of interest

The authors declare no conflict of interest.

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Correspondence to Alan E. Tonelli.

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Gurarslan, A., Shen, J., Caydamli, Y. et al. Pyriproxyfen cyclodextrin inclusion compounds. J Incl Phenom Macrocycl Chem 82, 489–496 (2015). https://doi.org/10.1007/s10847-015-0526-7

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  • DOI: https://doi.org/10.1007/s10847-015-0526-7

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