Study of the Reaction Derivatization Glyphosate and Aminomethylphosphonic Acid (AMPA) with N,O-Bis(trimethylsilyl)trifluoroacetamide

T. C. P. G. Catrinck, Maria Clara Santana Aguiar, Amanda Dias, Flaviano Oliveira Silvério, Paulo Henrique Fidêncio, Gevany Paulino de Pinho

Department of Chemistry, Universidade Federal dos Vales do Jequitinhonha e Mucuri, Diamantina, Brazil.
Institute of Agricultural Sciences, Universidade Federal de Minas Gerais, Montes Claros, Brazi.
Institute of Agricultural Sciences, Universidade Federal de Minas Gerais, Montes Claros, Brazil.

DOI: 10.4236/ajac.2013.411077                

Abstract

This work aimed to study the derivatization unprecedented of glyphosate and AMPA solutions using N,O-bis (trimethylsilyl)trifluoroacetamide (BSTFA) combined with trimethylchlorosilane (TMCS), evaluating the composition of the reaction medium, use of ultrasound, volume of BSTFA:pyridine and pH of the reaction medium. From this study it was inferred that the reaction medium was composed of BSTFA:pyridine in ratio 60:100, respectively, without ultrasonic vibration and pH adjustment that provide optimal conditions for analysis by GC-MS. Furthermore, the methodology used was simple and fast, and that was the most practical method commonly used.

Keywords

Glyphosate; GC-MS; Derivatization; BSTFA

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	S. M. Sanches, C. H. T. P. Silva, S. X. Campos and E. M. Vieira, “Pesticidas e seus Respectivos Riscos Associados à Contaminacao da água,” Pesticidas: R. Ecotoxicol. e Meio Ambiente, Vol. 13, No. 0, 2003, pp. 53-58.
[2]	B. Li, X. Deng, D. Guo and S. Jin, “Determination of Glyphosate and Aminomethylphosphonic Acid Residues in Foods Using High Performance Liquid Chromatography-Mass Spectrometry/Mass Spectrometry,” Chinese Journal of Chromatography, Vol. 25, No. 4, 2007, pp. 486-490. http://dx.doi.org/10.1016/S1872-2059(07)60017-0
[3]	M.-X. Chen, Z.-Y. Cao, Y. Jiang and Z.-W. Zhu, “Direct Determination of Glyphosate and Its Major Metabolite, Aminomethylphosphonic Acid, in Fruits and Vegetables by Mixed-Mode Hydrophilic Interaction/Weak Anion-Exchange Liquid Chromatography Coupled with Electrospray Tandem Mass Spectrometry,” Journal of Chromatography A, Vol. 1272, 2013, pp. 90-99. http://dx.doi.org/10.1016/j.chroma.2012.11.069
[4]	Y. V. Kryuchkova, G. L. Burygin, N. E. Gogoleva, Y. V. Gogolev, M. P. Chernyshova, O. E. Makarov, E. E. Fedorov and O. V. Turkovskaya, “Isolation and Characterization of a Glyphosate-Degrading Rhizosphere Stain, Enterobacter cloacae K7,” Microbiological Research, 2013, in press. http://dx.doi.org/10.1016/j.micres.2013.03.002
[5]	Z.-X, Guo, Q. Cai and Z. Yang, “Determination of Glyphosate and Phosphate in Water by Ion Chromatography-Inductively Coupled Plasma Mass Spectrometry Detection,” Journal of Chromatography A, Vol. 1100, No. 2, 2005, pp. 160-167. http://dx.doi.org/10.1016/j.chroma.2005.09.034
[6]	M. V. Khrolenko and P. P. Wieczorek, “Determination of Glyphosate and Its Metabolite Aminomethylphosphonic Acid in Fruit Juices Using Supported-Liquid Membrane Preconcentration method with High-Performance Liquid Chromatography and UV Detection after Derivatization with p-Toluenesulphonyl Chloride,” Journal of Chromatography A, Vol. 1093, No. 1-2, 2005, pp. 111-117. http://dx.doi.org/10.1016/j.chroma.2005.07.062
[7]	K. Q. Qian, T. Tang, T. Shi, F. Wang, J. Li and Y. Cao, “Residue Determination of Glyphosate in Environmental Water Samples with High-Performance Liquid Chromatography and UV Detection after Derivatization with 4-Chloro-3,5-dinitrobenzotrifluoride,” Analytica Chimica Acta, Vol. 635, No. 2, 2009, pp. 222-226. http://dx.doi.org/10.1016/j.aca.2009.01.022
[8]	H.-Y. Chiu, Z.-Y. Lin, H.-L. Tu and C.-W. Whang, “Analysis of Glyphosate and Aminomethylphosphonic Acid by Capillary Electrophoresis with Electrochemiluminescence Detection,” Journal of Chromatography A, Vol. 1177, No. 1, 2008, pp. 195-198. http://dx.doi.org/10.1016/j.chroma.2007.11.042
[9]	I. Hanke, H. Singer and J. Hollender, “Ultratrace-Level Determination of Glyphosate, Aminomethylphosphonic Acid and Glufosinate in Natural Waters by Solid-Phase Extraction Followed by Liquid Chromatography-Tandem Mass Spectrometry: Performance Tuning of Derivatization, Enrichment and Detection,” Analytical and Bioanalytical Chemistry, Vol. 391, No. 6, 2008, pp. 2265-2276. http://dx.doi.org/10.1007/s00216-008-2134-5
[10]	C. Druart, O. Delhomme, A. Vaufleuty, E. Ntcho and M. Millet, “Optimization of Extraction Procedure and Chromatographic Separation of Glyphosate, Glufosinate and Aminomethylphosphonic Acid in Soil,” Analytical and Bioanalytical Chemistry, Vol. 399, No. 4, 2011, pp. 1725-1732. http://dx.doi.org/10.1007/s00216-010-4468-z
[11]	C. Shummer, O. Delhomme, B. M. R. Appenzeller, R. Wennig and M. Millet, “Comparison of MTBSTFA and BSTFA in Derivatization Reactions of Polar Compounds Prior to GC/MS Analysis,” Talanta, Vol. 77, No. 4, 2009, pp. 1473-1482. http://dx.doi.org/10.1016/j.talanta.2008.09.043
[12]	T. A. Souza, M. H. R. Matta, é. Montagner and A. B. G. Abreu, “Estudo de Recuperacao de Glifosato e AMPA Derivados em Solo Utilizando-se Resinas Nacionais,” Química Nova, Vol. 29, No. 6, 2006, pp. 1372-1376. http://dx.doi.org/10.1590/S0100-40422006000600037
[13]	M. Motojyuku, T. Saito, K. Akieda, H. Otsuka, I. Yamamoto and S. Inokuchi, “Glyphosate Metabolites, and Glufosinate in Human Serum by Chromatography-Mass Spectrometry,” Journal of Chromatography B, Vol. 875, No. 2, 2008, pp. 509-514. http://dx.doi.org/10.1016/j.jchromb.2008.10.003
[14]	K. K. Ngim, J. Green, J. Cuzzi, M. Ocampo and Z. Gu, “Optimizad Derivatization Procedure for Characterizing (Aminomethyl)phosphonic Acid Impurities by GC-MS,” Journal of Chromatographic Science, Vol. 49, No. 1, 2011, pp. 8-14. http://dx.doi.org/10.1093/chrsci/49.1.8
[15]	M. B. Pessuto, I. C. Costa, A. B. Souza, F. M. Nicoli, J. C. P. Mello, F. Petereit and H. Luftmann, “Atividade Antioxidante de Extratos e Taninos Condensados das Folhas Maytenus ilicifolia Mart. ex Reiss,” Química Nova, Vol. 32, No. 2, 2009, pp. 412-416. http://dx.doi.org/10.1590/S0100-40422009000200027
[16]	J. R. Silva, L. T. Silva and J. I. Druzian, “Otimizacao e Validacao Intralaboratorial de Método para Análise de Resíduos de Cloranfenicol em Leite Caprino por Cromatografia Gasosa com Deteccao por Captura de Elétrons (CG/DCE),” Química Nova, Vol. 33, No. 1, 2010, pp. 90-96. http://dx.doi.org/10.1590/S0100-40422010000100017
[17]	X. Shen, C. Deng, B. Wang and L. Dong, “Quantification of Trimetilsilyl Derivatives of Amino Acid Disease Biomarkers in Neonatal Blood Samples by Gas Chromatography-Mass Spectrometry,” Analytical and Bioanalytical Chemistry, Vol. 384, No. 4, 2006, pp. 931-938. http://dx.doi.org/10.1007/s00216-005-0241-0
[18]	G. S. Garbellini, G. R. Salazar-Banda and L. A. Avaca, “Aplicacao do Ultra-Som em Sistemas Eletroquímicos: Consideracaes Teóricas e Experimentais,” Química Nova, Vol. 31, No. 1, 2008, pp. 123-133. http://dx.doi.org/10.1590/S0100-40422008000100024
[19]	V. M. Prata, E. S. Emídio and H. S. Dorea, “New Catalytic Ultrasound Method for Derivatization of 11-Nor-Δ9tetrahydrocannabinol-9-carboxylic Acid in Urine, with Analysis by GC-MS/MS,” Analytical and Bioanalytical Chemistry, Vol. 403, No. 2, 2012, pp. 625-632. http://dx.doi.org/10.1007/s00216-012-5827-8
[20]	I. M. C. Rodrigues, A. P. S. Souza Filho, F. A. Ferreira and A. J. Demuner, “Prospeccao Química de Compostos Produzidos por Senna Alata com Atividade Alelopática,” Planta Daninha, Vol. 28, No. 1, 2010, pp. 1-12.
[21]	C. F. B. Coutinho and L. H. Mazo, “Complexos Metálicos com o Herbicida Glyphosate: Revisao,” Química Nova, Vol. 28, No. 6, 2005, pp. 1038-1045. http://dx.doi.org/10.1590/S0100-40422005000600019