Spectroscopic and Electrochemical Investigations of N-(Phosphonomethyl)glycine (glyphosate) and (Aminomethyl)phosphonic Acid (AMPA)

A. Habekost^1,

¹Department of Chemistry, University of Education, Reuteallee 46, D-71634 Ludwigsburg, Germany

Cite this paper

A. Habekost. Spectroscopic and Electrochemical Investigations of N-(Phosphonomethyl)glycine (glyphosate) and (Aminomethyl)phosphonic Acid (AMPA). World Journal of Chemical Education. 2015; 3(6):134-140. doi: 10.12691/WJCE-3-6-2

Abstract

N-(Phosphonomethyl)glycin (glyphosate), known by the trade name of Roundup^®, is a broad-spectrum systemic herbicide used to kill several types of grass weed. It was first synthesized in 1970 by J. E. Franz, a chemist at the agrochemical corporation Monsanto. Glyphosate's mode of action is to inhibit a plant enzyme involved in the synthesis of some aromatic amino acids. There is some controversy at present about the use of Roundup^® because its hazard potential is not clear. In this article, we present some reliable and easily performed spectroscopic and electrochemical measurements to identify glyphosate isolated as well as in some commercial products. The analogous experiments apply to (Aminomethyl)phosphonic acid (AMPA), the hydrolysis product of glyphosate.

Keywords

Four year undergraduate/beginners of PhD students, analytical, electrochemistry, IR, MS, UVVISspectroscopy, hands-on learning/manipulatives

Copyright

This work is licensed under a Creative Commons Attribution 4.0 International License. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/

References

[1]	Kodama, S., Ito, Y., Taga, A., Nomura, Y., Yamamoto, A., Chinaka, S., Suzuki, K., Yamashita, T., Kemmei, T., and Hayakawa, K, A fast and simple analysis of glyphosate in tea beverageby capillary electrophoresis with on-line copper (II)-glyphosate complex formation, J. Health Sci., 54, 602-606 (2008).
[2]	Börjesson, E. andTorstensson, L, New methods for determination of glyphosate and (aminomethyl) phosphonic acid in water and soil , J.Chromatogr., 886, 207-216 (2000).
[3]	Deyrup, C.L., Chang S.M., Weitraub, R.A., Moye, H.A, Simultaneous esterification and acylation of pesticides for analysis by gas chromatography. 1. Derivatization of glyphosate and (aminomethly)phosphonic acid with fluorinated alcohols-perfluorinated anhydrides, J. Agric. Food Chem. 33, 944-947 (1985).
[4]	Chiu, H.Y., Lin, Z.Y., Tu, H.L., and Whang, C.W, Analysis of glyphosate and aminomethylphosphonic acid by capillary electrophoresis with electroluminescence detection, J. Chromatogr A, 1177, 195-198 (2008).
[5]	Sierra, E., Mendez, M.A., Sarria, V.M., and Cortes, M.T. Electrooxidatión de glifosatosobreelectrodos de níquel y cobre, Quim. Nova, 31, 220-226 (2008).
[6]	Sheals, J., Persoon, P., and Hedman, B., IR and EXAFS spectroscopic studies of glyphosate protonantion and copper (II) complexes of glyphosate an aqueous solution, Inorg. Chem., 40, 4302-4309 (2001).
[7]	Sheals, J., Granström, M., Sjöberg, S., and Persson, P., Coadsorption of Cu(II) and glyphosate at the water-goethite (α-FEOOH) interface: molecular structures from FTIR and EXAFS measurements, J. Colloid and Interface Science 262, 38-47 (2003).
[8]	http://www.eurl-pesticides.eu/library/docs/srm/1stws2006_lecture_christensen_glyphosate.pdf]. Delminoca, E.L., Bertozzi, J., de Souza, N.E., and Oloveira, C.C., Determination of glyphosate and aminomethylphosphonic acid for assessing the quality tap water using SPE and HPLC, ActaScientarium, 36, 513-519 (2014).
[9]	Piccolo, A. and Celano, G., Modification of infrared spectra of the herbicide glyphosate induced by pH variation, J. Environ. Sci. Health, B 28, 447-457 (1993).
[10]	Daniele, P.G., De Stefano, C., Prenesti, E., andSammartano, S. Copper (II) complexes of N-(phosphonomethyl)glycine in aqueous solution: a thermodynamic and spectrophotometric study, Talanta, 45, 425-431 (1997).
[11]	Pintado, S., Amaro, R.R., Mayen, M., and Mellado, J.M.R. Electrochemical determination of the glyphosate metabolite aminomethylphosphonic acid (AMPA) in drinking water with an electrodeposited copper electrode, Int. J. Electrochem. Sci. 7, 305-312 (2012).
[12]	Dos Santos, S.C., Galli, A., Felsner, M.L., and Justi, K.C.,Desenvolvimento de metodologiaeletroanalitica para a determinacao do pesticide glifosatoemamostrasambientais, Recista virtual de Quimica, 6, 866-883 (2014).
[13]	Coutinho, C.F.B., Coutinho, L.F.M., Mazo, L.H., Nixdorf, S.L., Camara, C.A.P., and Lancas, F.M., Direct determination of glyphosate using hydrophilic interaction chromatography with coulometric detection at copper microelectrode, Anal. Chim. Act., 592, 30-35 (2007). http://pubs.usgs.gov/tm/tm5a10/pdf/tm5a10.pdf.