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Amiben Metabolism in Plants I. Isolation and Identification of an N-glucosyl Complex

Published online by Cambridge University Press:  12 June 2017

C. R. Swanson ,
R. E. Kadunce ,
R. H. Hodgson  and
D. S. Frear
C. R. Swanson
Affiliation:
Crops Research Division, Agricultural Research Service, U. S. Department of Agriculture, Metabolism and Radiation Research Laboratory, State University Station, Fargo, North Dakota
R. E. Kadunce
Affiliation:
Crops Research Division, Agricultural Research Service, U. S. Department of Agriculture, Metabolism and Radiation Research Laboratory, State University Station, Fargo, North Dakota
R. H. Hodgson
Affiliation:
Crops Research Division, Agricultural Research Service, U. S. Department of Agriculture, Metabolism and Radiation Research Laboratory, State University Station, Fargo, North Dakota
D. S. Frear
Affiliation:
Crops Research Division, Agricultural Research Service, U. S. Department of Agriculture, Metabolism and Radiation Research Laboratory, State University Station, Fargo, North Dakota
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Abstract

The herbicide 3-amino-2,5-dichlorobenzoic acid (amiben) was converted to N-(3-carboxy-2,5-dichlorophenyl)-glucosylamine, N-glucosyl amiben, in roots of plants treated with amiben. Identification of N-glucosyl amiben was accomplished by means of thin-layer and gas chromatography and confirmed by infrared spectroscopy. The postulated metabolite was synthesized and found to be identical with the product of amiben metabolism in plants.

Type
Research Article
Information
Weeds , Volume 14 , Issue 4 , October 1966 , pp. 319 - 323
Copyright
Copyright © 1966 Weed Science Society of America 

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References

Literature Cited

1. Bache, C. A. 1964. Note on the estimation of amiben in tomatoes by thin layer chromatography. J. Assoc. Offic. Agr. Chem. 47:355.Google Scholar
2. Baker, R. S. and Warren, G. F. 1962. Selective herbicidal action of amiben on cucumber and squash. Weeds 10:219–223.Google Scholar
3. Cassil, C. C. 1962. Pesticide residue analysis by microcoulometric gas chromatography. In Gunther, F. A., ed., Residue Reviews 1:37–65. Acad. Press. New York.Google Scholar
4. Colby, S. R. 1965. Herbicide metabolism: N-glycoside of amiben isolated from soybean plants. Science 150:619–620.CrossRefGoogle ScholarPubMed
5. Colby, S. R., Warren, G. F., and Baker, R. S. 1964. Fate of amiben in tomato plants. J. Agr. Food Chem. 12:320–321.Google Scholar
6. Haugaard, G. and Tumerman, L. 1956. Reactions of aldoses with amino compounds. Arch. Biochem. Biophys. 65:86–92.Google Scholar
7. Hough, L., Jones, J. K. N., and Wadman, W. H. 1950. Quantitative analysis of mixtures of sugars by the method of partition chromatography. Part V. Improved methods for the separation and detection of the sugars and their methylated derivatives on the paper chromatogram. J. Chem. Soc. part 11:1702–1706.CrossRefGoogle Scholar
8. Kapadia, G. J. and Zalucky, T. B. 1964. Chromogenic activity of carbonyl-substituted resorcinols with Ehrlich reagent. J. Chromatog. 15:76–79.Google Scholar
9 Mitchell, F. and Schleppinghof, B. 1956. Zur Kenntnis der Amadori-Umlagerung. Chem. Ber. 89:1702–1708.CrossRefGoogle Scholar
10. Peters, E. J., Gebhardt, M. R., and Stritzke, J. F. 1965. Interrelations of row spacings, cultivations and herbicides for weed control in soybeans. Weeds 13:285–289.Google Scholar
11. Reddi, R. K. and Kodicek, E. 1953. Metabolism of nicotinic acid and related compounds in man and rat. Biochem. J. 53:286–294.Google Scholar
12. Richey, Jane M., Richey, H. G. Jr., and Schraer, Rosemary. 1964. Quantitative analysis of carbohydrates using gas-liquid chromatography. Anal. Biochem. 9:272–280.CrossRefGoogle ScholarPubMed
13. Schlenk, H. and Gellerman, J. L. 1960. Esterification of fatty acids with diazomethane. Anal. Chem. 34:1412.Google Scholar
14. Sheets, T. J. 1963. Photochemical alteration and inactivation of amiben. Weeds 11:186–190.Google Scholar
15. Swanson, C. R., Hodgson, R. H., and Frear, D. S. 1965. A major metabolite of 3-amino-2,5-dichlorobenzoic acid (amiben) in plants. Pl. Physiol. (Suppl.) 40:xiv.Google Scholar
16. Sweeley, C. C., Bentley, R., Marita, M., and Wells, W. W. 1963. Gas liquid chromatography of trimethylsilyl derivatives of sugars and related substances. J. Am. Chem. Soc. 85:2497–2507.CrossRefGoogle Scholar
17. Zweig, G. 1963. Analytical methods for pesticides, plant growth regulators and food additives. Vol. 1:219. Acad. Press. New York.Google Scholar