Structure of the β-cyclodextrin: acetamiprid insecticide inclusion complex in solution and solid state

Abstract

The molecular microencapsulation process, through the formation of the inclusion complex with β-cyclodextrin (β-CD), shows numerous environmental and industrial cost advantages, such as, stability improvement of the active substance, synthesis of water-based products, option of commercializing the final product either in solid state or in solution and avoidance of the undesired side-effects derived from the use of insecticides. Furthermore, the inclusion complexes have other advantages that involve controlled and specific release of active component in the medium. In this work the synthesis of the inclusion complex formed by β-CD and the acetamiprid (ACET) nicotinoid insecticide ((E)-N1-[(6-chloro-3-pyridyl)methyl]-N2-cyano-N1-methyl-acetamidine) was done and their molecular structure was studied in solid state and in solution, by means of experimental techniques. The 2:2 stoichiometry found in solid state, a structure based on dimmers classified as a channel type, is similar to that found in solution (1:1 stoichiometry). In both cases, the nitrile and chloropyridine groups of the insecticide molecules are oriented toward primary rim and secondary rim of the β-CD molecule, respectively.

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Acknowledgments

Authors thank the Basque Country Government for financial support (Project IT789-13). They also thank the technicians of SGIkers for a generous allocation of SXRD measurements, financed by the national program for the promotion of human resources within the national plan of scientific research, development and innovation, “Ministerio de Ciencia e Innovación”, Fondo Social Europeo (FSE)” and “Gobierno Vasco, Dirección de Politica Cientifica”. And finally, authors thank the Cambridge Crystallographic Data Centre (CCDC) by the number of Crystallographic Deposition, 1046865.

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Correspondence to Maria Luz Alonso.

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Alonso, M.L., Sebastián, E., Felices, L.S. et al. Structure of the β-cyclodextrin: acetamiprid insecticide inclusion complex in solution and solid state. J Incl Phenom Macrocycl Chem 86, 103–110 (2016). https://doi.org/10.1007/s10847-016-0645-9

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Keywords

  • Acetamiprid (ACET)
  • β-cyclodextrin (β-CD)
  • Single crystal and powder X-ray diffraction (XRD)
  • Fourier transform infrared spectroscopy (FTIR)
  • 1D and 2D Nuclear magnetic resonance spectroscopy (NMR)