Hostname: page-component-78c5997874-v9fdk Total loading time: 0 Render date: 2024-11-10T07:31:02.741Z Has data issue: false hasContentIssue false

Preemergence and Postemergence Activities of the (R) and (S) Enantiomers of Haloxyfop

Published online by Cambridge University Press:  12 June 2017

B. Clifford Gerwick
Affiliation:
Agric. Products Res., The Dow Chem. Co., 2800 Mitchell Drive, Walnut Creek, CA 94598
Lucinda A. Jackson
Affiliation:
Agric. Products Res., The Dow Chem. Co., 2800 Mitchell Drive, Walnut Creek, CA 94598
Jack Handly
Affiliation:
Agric. Products Res., The Dow Chem. Co., 2800 Mitchell Drive, Walnut Creek, CA 94598
Nick R. Gray
Affiliation:
Agric. Products Res., The Dow Chem. Co., 2800 Mitchell Drive, Walnut Creek, CA 94598
John W. Russell
Affiliation:
Analytical Laboratories, The Dow Chem. Co., Midland, MI 48460

Abstract

The relative activities of (R) and (S) enantiomers of the methyl ester of haloxyfop were determined on annual grasses. Samples enriched in the (S) enantiomer were markedly less active than the (R) in petri dish evaluations and foliar applications. The pure (S) enantiomer was estimated by regression to be 1000-fold or less active than the (R). The activity of the (S) enantiomer was found to be equivalent to that of the (R) following preemergence applications. Isolation and characterization of haloxyfop from soil treated with the methyl ester of haloxyfop indicated inversion of the (S) enantiomer to the (R) enantiomer within 7 days. Field trials confirmed the differential activity of enantiomers applied postemergence and their equivalence when applied preemergence. These findings indicate that inversion of the (S) enantiomer to the (R) occurs in soil following preemergence applications.

Type
Physiology, Chemistry, and Biochemistry
Copyright
Copyright © 1988 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. Barrett, D.W.A. and Sutton, P. B. 1985. Grass weed control in winter oilseed rape with isomers of fluazifop-butyl. Proc. Br. Crop Prot. Conf. – Weeds 1:231238.Google Scholar
2. Bewick, D. W. 1986. Stereochemistry of fluazifop-butyl transformations in soil. Pestic. Sci. 17: 349356.Google Scholar
3. Buhler, D. D. and Burnside, O. C. 1984. Herbicidal activity of fluazifop-butyl, haloxyfop-methyl, and sethoxydim in soil. Weed Sci. 32:824831.Google Scholar
4. Gillespie, G. R. and Nalewaja, J. D. 1986. Postemergence grass control herbicides applied to the soil. Weed Sci. 34:942947.Google Scholar
5. Nestler, H. J. and Bieringer, H. 1980. Synthesis and herbicidal activity of the D- and L-methyl 2-[4-(2,4-dichlorophenoxy)-phenoxy]-propionate enantiomers. Z. Naturforsch. 35b 366371.Google Scholar
6. Sakata, G., Makino, K., Morimoto, K., Ikai, T., and Hasebe, S. 1985. Synthesis and herbicidal activity of optically active ethyl 2-[4-(6-chloro-2-quinoxalinyoxy)phenoxy] propanoate. J. Pestic. Sci. 10:6973.Google Scholar
7. Sakata, G., Makino, K., Kusano, K., Satow, J., Ikai, T., and Suzuki, K. 1985. Preparation of optically pure ethyl (R)–(+) and (S)–(–) 2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy] propanoate by resolution method and their herbicidal activities. J. Pestic. Sci. 10:7579.Google Scholar
8. Souter, R. W. 1985. Chromatographic separations of stereoisomers. CRC Press, Boca Raton, Florida. 241 pp.Google Scholar
9. Uchiyama, M., Washio, N., Ikai, T., Igarashi, H., and Suzuki, K. 1986. Stereospecific responses to (R)–(+) and (S)–(–) quizalofopethyl in tissues of several plants. J. Pestic. Sci. 11:459467.Google Scholar