Hostname: page-component-5c6d5d7d68-wpx84 Total loading time: 0 Render date: 2024-08-16T13:35:40.094Z Has data issue: false hasContentIssue false

Hydroxylation of 2,4-D in Several Weed Species

Published online by Cambridge University Press:  12 June 2017

J. Fleeker
Affiliation:
Dep. of Biochem., North Dakota State Univ., Fargo, North Dakota 58102
R. Steen
Affiliation:
Dep. of Biochem., North Dakota State Univ., Fargo, North Dakota 58102

Abstract

Wild buckwheat (Polygonum convolvulus L.), leafy spurge (Euphorbia esula L.), yellow foxtail [Setaria glauca (L.) Beauv.], and wild oat (Avena fatua L.) hydroxylated, in a 7-day period, 2 to 7% of the (2,4-dichlorophenoxy)acetic acid-1-14C (2,4-D-1-14C) absorbed. Only a trace of hydroxylation products was detected in wild mustard [Brassica kaber (DC.) L. C. Wheeler var. pinnatifida (Stokes) L. C. Wheeler], perennial sowthistle (Sonchus arvensis L.), and kochia [Kochia scoparia (L.) Roth]. The investigation was limited to hydroxylation on the para-position of the herbicide. The predominant product, 2,5-dichloro-4-hydroxyphenoxyacetic acid, was detected in all weed species studied. Also found in measurable amounts in some species were 2,3-dichloro-4-hydroxyphenoxyacetic acid and 2-chloro-4-hydroxyphenoxyacetic acid. The hydroxylation rate on the number four carbon of the ring did not account for the variation in susceptibility exhibited by these plants.

Type
Research Article
Copyright
Copyright © 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. Ames, B. N. and Mitchell, H. K. 1952. The paper chromatography of imidazoles. J. Amer. Chem. Soc. 74:252253.Google Scholar
2. Baille, L. A. 1969. Determination of liquid scintillation counting efficiencies by pulse-height shift. Int. J. Appl. Radiat. and Isotop. 8:17.CrossRefGoogle Scholar
3. Brown, J. P. and McCall, E. B. 1955. Some chlorinated hydroxyphenoxyacetic acids. J. Chem. Soc: 36813687.CrossRefGoogle Scholar
4. Clark, T. H. 1892. The addition-products of benzo- and of toluquinone. Amer. Chem. J. 14:553576.Google Scholar
5. Eckert, A. and Endler, R. 1922. Chlorierung von hydrochinol. J. prakt. Chem. 104:81–4.Google Scholar
6. Glaze, N. C. and Wilcox, M. 1966. GLC analysis for hydroxydichlorophenoxyacetic acids in roots treated with 2,4-D. Soil and Crop Sci. Soc. of Florida 26:271277.Google Scholar
7. Hamilton, R. H., Hurter, J., Hall, J. K., and Ercegovich, C. D. 1971. Metabolism of phenoxyacetic acids. I. Metabolism of 2,4-dichlorophenoxyacetic acid and 2,4,5-trichlorophenoxyacetic acid by bean plants. J. Agr. Food Chem. 19:(in press).CrossRefGoogle Scholar
8. Hoagland, D. R. and Arnon, D. I. 1938. Water Culture method for growing plants without soil. California Agr. Exp. Sta. Circ. 347:139.Google Scholar
9. Holley, R. W. 1952. Studies on the fate of radioactive 2,4-dichlorophenoxyacetic acid in bean plants. II. A water-soluble transformation product of 2,4-D. Arch. Biochem. Biophys. 35:171175.Google Scholar
10. Klingman, G. C. 1961. Weed Control as a Science. John Wiley and Sons, New York. 421 p.Google Scholar
11. Ramirez, F., Chen, E. H., and Dershowitz, S. 1959. Reaction of trialkyl phosphites with p-benzoquinone and with other symmetrically substituted p-quinones. A new synthesis of hydroquinone monoalkyl ethers. J. Amer. Chem. Soc. 81:43384342.CrossRefGoogle Scholar
12. Thomas, E. W. and Loughman, B. C. 1964. Metabolic fate of 2,4-dichlorophenoxyacetic acid in the stem tissue of Phaseolus vulgaris . Nature 204:884885.Google Scholar