Hostname: page-component-586b7cd67f-gb8f7 Total loading time: 0 Render date: 2024-11-25T09:26:09.243Z Has data issue: false hasContentIssue false

Uptake, Translocation, and Metabolism of Propham by Wheat (Triticum aestivum), Sugarbeet (Beta vulgaris), and Alfalfa (Medicago sativa)

Published online by Cambridge University Press:  12 June 2017

M. E. Burt
Affiliation:
Dep. Crop Sci., North Carolina State Univ., Raleigh, NC 27607
F. T. Corbin
Affiliation:
Dep. Crop Sci., North Carolina State Univ., Raleigh, NC 27607

Abstract

Uptake, translocation, and metabolism of propham (isopropyl carbanilate) were ascertained for wheat (Triticum aestivum L., ‘Neepawa’) sugarbeet (Beta vulgaris L., ‘HH-10’), and alfalfa (Medicago sativa L., ‘Cherokee’) when grown in either liquid culture or in soil. Three-week-old wheat and 5-week-old sugarbeet and alfalfa plants were treated with 14C-propham in liquid culture for 1, 2, and 4 days. Other plants were placed in treated soil at 10 weeks after germination and grown for 15 weeks. Wheat absorbed 98%, sugarbeet 93%, and alfalfa 81% of the propham from solution after 4 days. Propham was translocated in all species. Under liquid culture, three polar metabolites of propham were isolated from wheat and alfalfa extracts and one was isolated from sugarbeet extracts. The agylcone moiety of the two most polar wheat metabolites was isopropyl-4-hydroxycarbanilate and that of the least polar metabolite was isopropyl-2-hydroxycarbanilate. The aglycone of all alfalfa and sugarbeet polar metabolites was isopropyl-4-hydroxycarbanilate. Only one polar metabolite was isolated from all soil-treated plants. The aglycone moiety was determined to be isopropyl-4-hydroxycarbanilate. Of the propham absorbed 95, 91, 89, and 36% was metabolized by sugarbeet roots, sugarbeet leaves, wheat leaves, and alfalfa leaves, respectively, after a 4-day liquid culture treatment. Propham was 100% metabolized when applied to plants via soil application.

Type
Research Article
Copyright
Copyright © 1978 by the 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. Baldwin, R. E., Freed, V. H., and Fang, S. C. 1954. Herbicide action: Absorption and translocation of carbon-14 applied as O-isopropyl N-phenyl carbamate in Avena and Zea . J. Agric. Food Chem. 2:428430.Google Scholar
2. Baskakov, Y. A. and Zemskaya, V. A. 1959. The possibility of transformation of carbanilate esters in plants. Sov. Plant Physiol. 6:164167.Google Scholar
3. Blankendaal, L., Hodgson, R. H., Davis, D. G., Hoerauf, R. A., and Shimabukuro, R. H. 1972. Growing plants without soil for experimental use. U. S. Dep. Agric. Misc. Publ. 1251, 17 pp.Google Scholar
4. Burschel, P. and Freed, V. H. 1959. The decomposition of herbicides in soils. Weeds 7:157161.CrossRefGoogle Scholar
5. Clark, C. G. and Wright, S. J. L. 1970. Degradation of the herbicide isopropyl N-phenylcarbamate by Arthrobacter and Achromabacter spp. from soil. Soil Biol. Biochem. 2:217266.Google Scholar
6. Dorough, H. W. and Wiggins, O. J. 1969. Nature of water-soluble metabolites of carbaryl in bean plants and their fate in rats. J. Econ. Entomol. 62:4953.CrossRefGoogle Scholar
7. Frear, D. S. and Swanson, H. R. 1974. Monuron metabolism in excised Gossypium hirsutum leaves: Aryl hydroxylation and conjugation of 4-chlorophenylurea. Phytochemistry 13:357360.Google Scholar
8. Hogue, E. J. and Warren, G. F. 1968. Selectivity of linuron on tomato and parsnip. Weed Sci. 16:5154.CrossRefGoogle Scholar
9. Honeycutt, R. C. and Adler, I. L. 1975. Characterization of bound residues of nitrogen in rice and wheat straw. J. Agric. Food Chem. 23:10971101.CrossRefGoogle Scholar
10. James, C. S. and Prendeville, G. N. 1969. Metabolism of chlorpropham (isopropyl m-chlorocarbanilate) in various plant species. J. Agric. Food Chem. 17:12571260.Google Scholar
11. Kaufman, D. D. 1967. Degradation of carbamate herbicides in soil. J. Agric. Food Chem. 15:582597.CrossRefGoogle Scholar
12. Kaufman, D. D. and Blake, J. 1973. Microbial degradation of several acetamide, acylanilide, carbamate, toluidine, and urea pesticides. Soil Biol. Biochem. 5:297308.Google Scholar
13. Kearney, P. C. and Konston, A. 1976. A simple system to simultaneously measure volatility and metabolism of pesticides from soil. J. Agric. Food Chem. 24:424426.Google Scholar
14. Kelly, R. G., Peets, E. A., Gordon, S., and Buyske, D. A. 1961. Determination of C14 and H3 in biological samples by Schoniger combustion and liquid scintillation techniques. Anal. Biochem. 2:267273.CrossRefGoogle Scholar
15. Kuhr, R. J. 1970. Metabolism of carbamate insecticide chemicals in plants and insects. J. Agric. Food Chem. 18:10231030.Google Scholar
16. Kuhr, R. J. and Casida, J. E. 1967. Persistent glycosides of metabolites of methylcarbamate insecticide chemicals formed by hydroxylation in bean plants. J. Agric. Food Chem. 15:814824.CrossRefGoogle Scholar
17. Newman, A. S., DeRose, R. H., and Derigo, H. T. 1948. Persistence of isopropyl N-phenyl carbamate in soils. Soil Sci. 66:393397.Google Scholar
18. Parochetti, J. V. and Warren, G. F. 1968. Biological activity and dissipation of IPC and CIPC. Weed Sci. 16:1315.Google Scholar
19. Patterson, M. S. and Greene, R. C. 1965. Measurement of low energy beta-emitters by liquid scintillation counting of emulsions. Anal. Chem. 37:854857.CrossRefGoogle ScholarPubMed
20. Pridham, S. B. 1965. Phenol-carbohydrate derivatives in higher plants. Adv. Carbohydr. Chem. 20:106114.Google ScholarPubMed
21. Schutte, H. R., Siegel, G., Held, P., and Jumar, A. 1971a. The absorption, translocation and elimination of propham in sugarbeets. Isotopenpraxis 7:274292.Google Scholar
22. Schutte, H. R., Siegel, G., Held, P., and Jumar, A. 1971b. Metabolism and behavior of residues from the propham in sugarbeets. Isotopenpraxis 7:330343.Google Scholar
23. Still, G.G. and Mansager, E. R. 1971. Metabolism of isopropyl-3-chlorocarbanilate by soybean plants. J. Agric. Food Chem. 19:879884.Google Scholar
24. Still, G. G. and Mansager, E. R. 1972. Aryl hydroxylation of isopropyl-3-chlorocarbanilate by soybean plants. Phytochemistry 11:515520.Google Scholar
25. Still, G. G. and Mansager, E. R. 1973a. Metabolism of isopropyl carbanilate by soybean plants. Pestic. Biochem. Physiol. 3:289299.Google Scholar
26. Still, G. G. and Mansager, E. R. 1973b. Soybean shoot metabolism of isopropyl-3-chlorocarbanilate: ortho and para aryl hydroxylation. Pestic. Biochem. Physiol. 3:8795.Google Scholar
27. Still, G. G. and Mansager, E. R. 1973c. Metabolism of isopropyl-3-chlorocarbanilate by cucumber plants. J. Agric. Food Chem. 3:697718.Google Scholar
28. Still, G. G. and Mansager, E. R. 1975. Alfalfa metabolism of propham. Pestic. Biochem. Physiol. 5:515522.CrossRefGoogle Scholar
29. Weidmann, J. L., Ecke, G. C., and Still, G. G. 1976. Synthesis and isolation of 1-hydroxy-2-chlorocarbanilate from soybean plants treated with isopropyl-3-chlorocarbanilate. J. Agric. Food Chem. 24:588592.Google Scholar