Identity and Activity of 2,4-Dichlorophenoxyacetic Acid Metabolites in Wild Radish (Raphanus raphanistrum)

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Synthetic auxin herbicides, such as 2,4-dichlorophenoxyacetic acid (2,4-D), are widely used for selective control of broadleaf weeds in cereals and transgenic crops. Although the troublesome weed wild radish (Raphanus raphanistrum) has developed resistance to 2,4-D, no populations have yet displayed an enhanced capacity for metabolic detoxification of the herbicide, with both susceptible and resistant wild radish plants readily metabolizing 2,4-D. Using mass spectrometry and nuclear magnetic resonance, the major 2,4-D metabolite was identified as the glucose ester, and its structure was confirmed by synthesis. As expected, both the endogenous and synthetic compounds retained auxin activity in a bioassay. The lack of detectable 2,4-D hydroxylation in wild radish and the lability of the glucose ester suggest that metabolic 2,4-D resistance is unlikely to develop in this species.

Original languageEnglish
Pages (from-to)13378-13385
Number of pages8
JournalJournal of Agricultural and Food Chemistry
Volume66
Issue number51
DOIs
Publication statusPublished - 26 Dec 2018

Fingerprint

Raphanus raphanistrum
Raphanus
2,4-Dichlorophenoxyacetic Acid
radishes
Metabolites
2,4-D
metabolites
Indoleacetic Acids
Herbicides
auxins
Esters
herbicides
metabolic detoxification
esters
Glucose
broadleaf weeds
Detoxification
Hydroxylation
glucose
Bioassay

Cite this

@article{dd5411545a8b4af299e0f03bdf29c98a,
title = "Identity and Activity of 2,4-Dichlorophenoxyacetic Acid Metabolites in Wild Radish (Raphanus raphanistrum)",
abstract = "Synthetic auxin herbicides, such as 2,4-dichlorophenoxyacetic acid (2,4-D), are widely used for selective control of broadleaf weeds in cereals and transgenic crops. Although the troublesome weed wild radish (Raphanus raphanistrum) has developed resistance to 2,4-D, no populations have yet displayed an enhanced capacity for metabolic detoxification of the herbicide, with both susceptible and resistant wild radish plants readily metabolizing 2,4-D. Using mass spectrometry and nuclear magnetic resonance, the major 2,4-D metabolite was identified as the glucose ester, and its structure was confirmed by synthesis. As expected, both the endogenous and synthetic compounds retained auxin activity in a bioassay. The lack of detectable 2,4-D hydroxylation in wild radish and the lability of the glucose ester suggest that metabolic 2,4-D resistance is unlikely to develop in this species.",
keywords = "2,4-dichlorophenoxyacetic acid, auxin, herbicide resistance, metabolism, wild radish (Raphanus raphanistrum)",
author = "Goggin, {Danica E.} and Nealon, {Gareth L.} and Cawthray, {Gregory R.} and Adrian Scaffidi and Howard, {Mark J.} and Powles, {Stephen B.} and Flematti, {Gavin R.}",
year = "2018",
month = "12",
day = "26",
doi = "10.1021/acs.jafc.8b05300",
language = "English",
volume = "66",
pages = "13378--13385",
journal = "Journal of Agricultural and Food Chemistry",
issn = "0021-8561",
publisher = "American Chemical Society",
number = "51",

}

TY - JOUR

T1 - Identity and Activity of 2,4-Dichlorophenoxyacetic Acid Metabolites in Wild Radish (Raphanus raphanistrum)

AU - Goggin, Danica E.

AU - Nealon, Gareth L.

AU - Cawthray, Gregory R.

AU - Scaffidi, Adrian

AU - Howard, Mark J.

AU - Powles, Stephen B.

AU - Flematti, Gavin R.

PY - 2018/12/26

Y1 - 2018/12/26

N2 - Synthetic auxin herbicides, such as 2,4-dichlorophenoxyacetic acid (2,4-D), are widely used for selective control of broadleaf weeds in cereals and transgenic crops. Although the troublesome weed wild radish (Raphanus raphanistrum) has developed resistance to 2,4-D, no populations have yet displayed an enhanced capacity for metabolic detoxification of the herbicide, with both susceptible and resistant wild radish plants readily metabolizing 2,4-D. Using mass spectrometry and nuclear magnetic resonance, the major 2,4-D metabolite was identified as the glucose ester, and its structure was confirmed by synthesis. As expected, both the endogenous and synthetic compounds retained auxin activity in a bioassay. The lack of detectable 2,4-D hydroxylation in wild radish and the lability of the glucose ester suggest that metabolic 2,4-D resistance is unlikely to develop in this species.

AB - Synthetic auxin herbicides, such as 2,4-dichlorophenoxyacetic acid (2,4-D), are widely used for selective control of broadleaf weeds in cereals and transgenic crops. Although the troublesome weed wild radish (Raphanus raphanistrum) has developed resistance to 2,4-D, no populations have yet displayed an enhanced capacity for metabolic detoxification of the herbicide, with both susceptible and resistant wild radish plants readily metabolizing 2,4-D. Using mass spectrometry and nuclear magnetic resonance, the major 2,4-D metabolite was identified as the glucose ester, and its structure was confirmed by synthesis. As expected, both the endogenous and synthetic compounds retained auxin activity in a bioassay. The lack of detectable 2,4-D hydroxylation in wild radish and the lability of the glucose ester suggest that metabolic 2,4-D resistance is unlikely to develop in this species.

KW - 2,4-dichlorophenoxyacetic acid

KW - auxin

KW - herbicide resistance

KW - metabolism

KW - wild radish (Raphanus raphanistrum)

UR - http://www.scopus.com/inward/record.url?scp=85059510434&partnerID=8YFLogxK

U2 - 10.1021/acs.jafc.8b05300

DO - 10.1021/acs.jafc.8b05300

M3 - Article

VL - 66

SP - 13378

EP - 13385

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

SN - 0021-8561

IS - 51

ER -