Hostname: page-component-586b7cd67f-2plfb Total loading time: 0 Render date: 2024-11-30T21:58:57.104Z Has data issue: false hasContentIssue false
  • English
  • Français

Translocation and Metabolism of Pyridinyloxyphenoxypropionate Herbicides in Rhizomatous Quackgrass (Agropyron repens)

Published online by Cambridge University Press:  12 June 2017

Paul Hendley ,
John W. Dicks ,
Thomas J. Monaco ,
Susan M. Slyfield ,
O. John Tummon  and
John C. Barrett
Paul Hendley
Affiliation:
Imperial Chemical Industries (ICI) Plc., Plant Prot. Div., Jealott's Res. Stn., Bracknell RG12 6EY, England
John W. Dicks
Affiliation:
Imperial Chemical Industries (ICI) Plc., Plant Prot. Div., Jealott's Res. Stn., Bracknell RG12 6EY, England
Thomas J. Monaco
Affiliation:
Dep. of Hortic. Sci., North Carolina State Univ., Raleigh, NC 27695-7609
Susan M. Slyfield
Affiliation:
ICI Plc.
O. John Tummon
Affiliation:
ICI Plc.
John C. Barrett
Affiliation:
ICI Plc.
Get access Rights & Permissions [Opens in a new window]

Abstract

Radiolabeled (14C) 2-[4-(3-chloro-5-trifluoromethyl-2-pyridinyloxy)phenoxy] propionic acid (Compound C); its methyl-,n-butyl-, and ethoxyethyl-esters; and fluazifop-butyl {(±)-butyl 2-[4-[(5-(trifluoromethyl)-2-pyridinyl)oxy] phenoxy] propionate} were applied to the primary shoots of young rhizomatous quackgrass [Agropyron repens (L.) Beauv. # AGRRE]. Plants were sampled from 0.5 to 24 days after treatment (DAT) and analyzed for radiochemical. All treatments caused phytotoxic symptoms in primary shoots, rhizomes, and tillers and significantly reduced growth of primary shoots and rhizomes. Treatment with compound C or its methyl and butyl esters eliminated regrowth from all rhizomes excised from treated plants. The ethoxyethyl-ester and fluazifop-butyl controlled regrowth from rhizomes from 50% of the plants and substantially reduced shoot regrowth from the remainder. Rhizomes that did produce shoots contained significantly less radiochemical than those from which no regrowth occurred. At 24 DAT, a maximum of only 1% of each radiochemical applied was translocated to the first tiller and rhizomes and had been sufficient to cause marked phytotoxic symptoms. Soon after application (1 DAT), the major metabolites in the treated leaves and remainder of the plant for all compounds were the free acid and substantial amounts of polar conjugates that were hydrolyzable to the free acids. Radiochromatography of extracts from rhizomes and first tillers from all treatments gave similar chemical profiles, with the free acids and their conjugates as the predominant components present. These results provide evidence that esters of the pyridinyloxyphenoxypropionic acids are rapidly hydrolyzed after absorption by quackgrass; the free acids are then translocated and are the active form of these herbicides.

Keywords

Aryloxypropionic acids; n-butylethoxyethylmethyl estersde-esterificationconjugationlipophilic conjugatesrhizome regrowthAGRRE
Type
Physiology, Chemistry, and Biochemistry
Information
Weed Science , Volume 33 , Issue 1 , January 1985 , pp. 11 - 24
Copyright
Copyright © 1985 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. Almeida, F. S., Oliveira, V. F., and Manetti Filho, J. 1983. Selective control of grass weeds in soybeans with some recently developed post-emergence herbicides. Trop. Pest Manag. 29:261–266.Google Scholar
2. Ashton, F. M. and Crafts, A. S. 1973. Mode of action of herbicides. Wiley-Interscience Publ., New York. 504 pp.Google Scholar
3. Boldt, P. F. and Putnam, A. R. 1981. Selectivity mechanisms for foliar applications of diclofop-methyl. II. Metabolism. Weed Sci. 29:237–241.Google Scholar
4. Chandrasena, J.P.N.R. and Sagar, G. R. 1984. Effects of fluazifop-butyl on shoot growth and rhizome buds of Elymus repens (L.) Gould. Weed Res. 24:297–303.CrossRefGoogle Scholar
5. Crafts, A. S. 1960. Evidence for hydrolysis of esters of 2, 4-D during absorption by plants. Weeds 8:19–25.Google Scholar
6. Fawcett, C. H., Wain, R. L., and Wightman, F. 1960. The metabolism of 3-indolylalkanecarboxylic acids, and their amides, nitriles and methyl esters in plant tissues. Proc. R. Soc. London Ser. B 231–254.Google Scholar
7. Fedtke, C. and Schmidt, R. R. 1977. Chlorfenprop-methyl: Its hydrolysis in vivo and in vitro and a new principle for selective herbicidal action. Weed Res. 17:233–239.Google Scholar
8. Friesen, H. A., O'Sullivan, P. A., and Vanden Born, W. H. 1976. HOE 23408, a new selective herbicide for wild oats and green foxtail in wheat and barley. Can. J. Plant Sci. 56:567–578.Google Scholar
9. Hatzios, K. K. and Penner, D. 1982. Metabolism of herbicides in higher plants. Burgess Publ. Co., Minneapolis. 142 pp.Google Scholar
10. Hill, B. D., Stobbe, E. H., and Jones, B. L. 1978. Hydrolysis of the herbicide benzoylprop ethyl by wild oat esterase. Weed Res. 18:149–154.Google Scholar
11. Hutson, D. H. 1982. Formation of lipophilic conjugates of pesticides and other xenobiotic compounds. Pages 171–184 in Hutson, D. H. and Roberts, T. R., eds. Progress in Pesticide Biochemistry. Volume 2. John Wiley & Sons, Limited, Chichester, England.Google Scholar
12. Jain, R. and Vanden Born, W. H. 1983. Morphological and histological effects of sethoxydim, fluazifop-butyl and Dowco 453 on wild oats (Avena fatua). Weed Sci. Soc. Am. Abstr. 23:73–74.Google Scholar
13. Jeffcoat, B. and Harris, W. N. 1973. Selectivity and mode of action of ethyl (±)-2-(N-benzoyl-3, 4-dichloroanilino) propionate in the control of Avena fatua in cereals. Pestic. Sci. 4:891–899.Google Scholar
14. Jeffcoat, B. and Harris, W. N. 1975. Selectivity and mode of action of flamprop-isopropyl, isopropyl (±)-2-[N-(3-chloro-4-fluorophenyl)benzamidol] propionate, in the control of Avena fatua in barley. Pestic. Sci. 6:283–296.Google Scholar
15. Knott, C. M. 1982. Post-emergence control of grass weeds in peas with fluazifop-butyl. Proc. 1982. Br. Crop. Prot. Conf. Weeds. 2:803–809.Google Scholar
16. Loos, M. A. 1975. Phenoxyalkanoic acids. Pages 1–28 in Kearney, P. C. and Kaufman, D. D., eds. Herbicides. Chemistry, degradation, and mode of action. Marcel Dekker, Inc., New York.Google Scholar
17. Nyffeler, A. and Gerber, H. R. 1981. CGA 82725-Ein neues nachauflaufherbizid gegen graser in dikotylen kulturen. Pages 252–253 in 43 Dtsch. Pflanzenschutz-Tagung, Hamburg.Google Scholar
18. Roberts, T. R. 1977. The metabolism of the herbicide flamprop-isopropyl in barley. Pestic. Biochem. Physiol. 7:378–390.Google Scholar
19. Shimabukuro, R. H., Walsh, W. C., and Hoerauf, R. A. 1979. Metabolism and selectivity of diclofop-methyl in wild oat and wheat. J. Agric. Food Chem. 27:615–622.Google Scholar
20. Velovitch, J. J. and Slife, F. W. 1983. Uptake, translocation and metabolism of fluazifop-butyl in foxtail millet [Setaria italica (L.) Beauv.] and common cocklebur (Xanthium pensylvanicum Wallr.). Weed Sci. Soc. Am. Abstr. 23:74.Google Scholar
21. Wain, R. L. and Smith, M. S. 1976. Selectivity in relation to metabolism. Pages 279–302 in Audus, L. J., ed. Herbicides–Physiology, Biochemistry, Ecology. Volume 2. Academic Press, Inc., New York.Google Scholar