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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.
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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 

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