Hostname: page-component-586b7cd67f-rcrh6 Total loading time: 0 Render date: 2024-11-28T23:26:19.620Z Has data issue: false hasContentIssue false

Methylation of Herbicides for Gas Chromatographic Determination

Published online by Cambridge University Press:  12 June 2017

E. A. Woolson
Affiliation:
Crops Research Division, Agricultural Research Service, U. S. Department of Agriculture, Beltsville, Maryland
C. I. Harris
Affiliation:
Crops Research Division, Agricultural Research Service, U. S. Department of Agriculture, Beltsville, Maryland
Get access

Abstract

Many acid herbicides must be methylated before analysis by gas-liquid chromatography. Several reagents were evaluated for the esterification of substituted acid herbicides. Esterification by the different methods was determined on 2,3,6-trichlorophenylacetic acid [fenac], 2,3,6-trichlorobenzoic acid [2,3,6-TBA], 4-amino-3,5,6-trichloropicolinic acid [picloram], 2-methoxy-3,6-dichlorobenzoic acid [dicamba], and 3,6-dichlorosalicylic acid, a possible metabolite of dicamba. The effect of substituent size and position is discussed in relation to esterification. The best methylating reagent for acid herbicides was diazomethane although it is toxic, explosive, and more costly than the other methods. BF3-methanol was equally as good when the compound was not sterically hindered. Water interfered with the esterification efficiency of all reagents. Diazomethane esterified the ammonium salt but not the sodium salt of the acids used.

Type
Research Article
Copyright
Copyright © 1967 Weed Science Society of America 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Literature Cited

1. Bache, C. A., Gutenmann, W. H., and Lisk, D. J. 1964. Determination of amiben in tomatoes by electron affinity gas chromatography. J. Agr. Food Chem. 12:185187.CrossRefGoogle Scholar
2. Gee, M. 1965. Methyl esterification of nonvolatile plant acids for gas chromatographic analysis. Anal. Chem. 37: 926928.CrossRefGoogle Scholar
3. Gould, E. S. 1959. Mechanism and Structure in Organic Chemistry. Holt, Rinehart, and Winston, New York. 790 p.Google Scholar
4. Kirkland, J. J. and Pease, H. L. 1964. Determination of polychlorinated benzoic acid herbicide residues by gas chromatography. J. Agr. Food Chem. 12:468472.CrossRefGoogle Scholar
5. Marquardt, R. P., Burchfield, H. P., Storrs, E. E., and Bevenue, A. 1964. 2,4-Dichlorophenoxyacetic Acid. p. 95116. In Zweig, G., Analytical Methods for Pesticides, Plant Regulators, and Food Additives. Academic Press, New York, New York. 269 p. Google Scholar
6. Metcalfe, L. D. and Schmitz, A. A. 1961. The rapid preparation of fatty acid esters for gas chromatographic analysis. Anal. Chem. 33:363366.CrossRefGoogle Scholar
7. Peterson, J. I., deSchmertzing, H., and Abel, K. J. 1965. Transesterification of lipids with BCl3 . J. Gas Chromatogr. 3:126130.CrossRefGoogle Scholar
8. Rogozinski, M. 1964. A rapid quantitative esterification technique for carboxylic acids. J. Gas Chromatogr. 2:136137.CrossRefGoogle Scholar
9. Rogozinski, M. 1964. The methanol-sulfuric acid esterification methods. J. Gas Chromatogr. 2:328329.CrossRefGoogle Scholar
10. Segal, H. S. and Sutherland, M. L. 1964. Comparison of flame ionization and electron capture detectors for the gas chromatographic evaluation of herbicide residues. p. 7379. In Gunther, F. A., Residue Reviews. Academic Press. New York, New York, 176 p. Google Scholar
11. Stanley, C. W. 1966. Derivatization of pesticide-related acids and phenols for gas chromatographic determination. J. Agr. Food Chem. 14:321323.CrossRefGoogle Scholar
12. Vorbeck, M. L., Mattick, L. R., Lee, F. A., and Pederson, C. S. 1961. Preparation of methyl esters of fatty acids for gas-liquid chromatography; quantitative comparison of methylation techniques. Anal. Chem. 33:15121514.CrossRefGoogle Scholar