Abstract
Trichlorfon or O,O-dimethyl-(2,2,2-trichloro-1-hydroxyethyl) phosphonate is an organophosphorus insecticide with cholinesterase inhibitor activity that has been widely used in protection of field and fruit crops. Trichlorfon rearranges to other more toxic organophosphate insecticides (such as dichlorvos at pH 6–8) in aqueous media. Trichlorfon is a thermally labile compound that cannot be easily determined by gas chromatography coupled with mass spectrometry (GC-MS) and has no functional group for sensitive detection by high performance liquid chromatography (HPLC). In this study, 31P dynamic nuclear magnetic resonance is used to elucidate the stability of trichlorfon and derivatives. These spectrums are compared with the theoretical studies with the Gaussian software to determine the stability and identify the structure. Two derivatives are identified by this method.
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References
J. M. Dust and C. S. Warren, Water Qual. Res. J. Can., 36, 589–604 (2001).
C. C. Chang, P. P. Lee, J. P. Hsu, et al., Aquaculture, 253, 653–666 (2006).
A. G. Frenich, M. J. Gonzaler-Rodriguez, F. J. Arrebola, et al., Anal. Chem., 77, 4640–4648 (2005).
Y. I. Chen, Y. S. Su, and J. F. Jen, J. Chromatogr. A, 976, 349–355 (2002).
C. Blasco, G. Font, and Y. Pco, J. Chromatogr. A, 970, 201–212 (2002).
F. Longobordi, M. Solfrizzo, D. Compagnone, et al., J. Agric. Food. Chem., 53(24), 9389–9394 (2005).
K. Futagami, C. Narazaki, Y. Kataoka, et al., J. Chromatogr. B. Biomed. Sci. Appl., 704, 369–373 (1997).
O. Segev, I. Columbus, Y. Ashani, et al., J. Org. Chem., 70, 309–314 (2005).
Z. Talebpour, A. R. Ghassempour, M. Zendehzaban, et al., Analytica Chem. Acta, 576, 290–296 (2006).
M. J. Frisch, G. W. Trucks, H. B Schlegel., et al., Gaussian-98, Revision A. 6, Gaussian, Inc.: Pittsburgh, PA (1998).
F. Boroit-Marqui, C. Demontety, V. Gilard, et al., Environ. Chem. Lett., 2, 93–97 (2004).
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Original Russian Text Copyright © 2011 by N. M. Najafi, R. Alizadeh, Z. Talebpour, and A. R. Ghassempour
Medicine Plant and Drugs Research Institute, Shahid Beheshti University, P.O. Box 19835-389, Tehran, Iran
The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 52, No. 4, pp. 735–739, July–August, 2011.
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Najafi, N.M., Alizadeh, R., Talebpour, Z. et al. 31P NMR and computer simulations of the structure of trichlorfon and its derivatives. J Struct Chem 52, 713–717 (2011). https://doi.org/10.1134/S002247661104010X
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DOI: https://doi.org/10.1134/S002247661104010X