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Metabolic Detoxification of Phenmedipham in Leaf Tissue of Tolerant and Susceptible Species

Published online by Cambridge University Press:  12 June 2017

H. Maelor Davies ,
Alexis Merydith ,
Liane Mende-Mueller  and
Alpo Aapola
H. Maelor Davies
Affiliation:
Calgene, Inc., 1920 Fifth St., Davis, CA 95616
Alexis Merydith
Affiliation:
Calgene, Inc., 1920 Fifth St., Davis, CA 95616
Liane Mende-Mueller
Affiliation:
Calgene, Inc., 1920 Fifth St., Davis, CA 95616
Alpo Aapola
Affiliation:
Res. Sci., Kemira Oy, Espoo Res. Ctr., P.O. Box 44, SF-02271, Espoo, Finland
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Abstract

Phenmedipham metabolism in leaf tissue of sugarbeet (tolerant) and rapeseed (sensitive) was compared. Sugarbeet leaf discs metabolized phenmedipham much more rapidly than rapeseed leaf discs, forming two metabolites of relatively low polarity. The less polar of these (metabolite 21) was a precursor to the other (metabolite 11), and its properties indicate derivation from phenmedipham by a single hydroxylation and monoglycosylation. Synthetic N-hydroxyphenmedipham was converted by both species into a compound that cochromatographs with metabolite 21. Purified metabolite 21 was much less inhibitory to light-driven oxygen evolution by isolated thylakoids of both species than was phenmedipham. Hydroxylation/glycosylation without prior carbamate hydrolysis appears to be a major factor in the tolerance of sugarbeet to phenmedipham.

Keywords

Phenmedipham, 3-[(methoxycarbonyl)amino]phenyl (3-methylphenyl)carbamatesugarbeet, Beta vulgaris L. ‘USH 11’rapeseed, Brassica napus ‘Westar’Herbicide toleranceherbicide metabolismBeta vulgarisBrassica napus
Type
Physiology, Chemistry, and Biochemistry
Information
Weed Science , Volume 38 , Issue 3 , May 1990 , pp. 206 - 214
Copyright
Copyright © 1990 by the Weed Science Society of America 

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