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 language | English |
|---|---|
| Pages (from-to) | 13378-13385 |
| Number of pages | 8 |
| Journal | Journal of Agricultural and Food Chemistry |
| Volume | 66 |
| Issue number | 51 |
| DOIs | |
| Publication status | Published - 26 Dec 2018 |
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Identity and Activity of 2,4-Dichlorophenoxyacetic Acid Metabolites in Wild Radish (Raphanus raphanistrum). / Goggin, Danica E.; Nealon, Gareth L.; Cawthray, Gregory R.; Scaffidi, Adrian; Howard, Mark J.; Powles, Stephen B.; Flematti, Gavin R.
In: Journal of Agricultural and Food Chemistry, Vol. 66, No. 51, 26.12.2018, p. 13378-13385.Research output: Contribution to journal › Article
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 -