Basis of Selectivity of the Herbicide Flupyrsulfuron-methyl in Wheat

Koeppe, Mary K.; Barefoot, Aldos C.; Cotterman, C. Daniel; Zimmerman, William T.; Leep, D.C

doi:10.1006/pest.1997.2314

Cited by 22 publications

(14 citation statements)

References 6 publications

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“…Flupyrsulfuron inhibits the biosynthesis of the essential amino acids valine and isoleucine, thus stopping cell division and plant growth. Selectivity derives from the rapid metabolism degradation of flupyrsulfuron in the wheat crop and tolerant plants and the very slow metabolism in weeds (Koeppe et al ., 1998). A method has been developed for the analysis of flupyrsulfuron in the soil of winter wheat crops using gas chromatography with electron capture detection (gc‐ecd) and combined gas chromatography–mass spectrometry (gc‐ms) after transformation of flupyrsulfuron into N‐(4,6‐dimethoxypyrimidine‐2‐yl)‐ N‐(3‐methoxycarbonyl‐6‐trifluoromethylpyridine‐2‐yl)methylamine 8 (Rouchaud ., 1999; Fig 1).…”

Section: Introductionmentioning

confidence: 99%

Soil metabolism of flupyrsulfuron in winter wheat crops

Rouchaud¹,

Moulard²,

Eelen³

et al. 2002

Weed Research

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The sulfonylurea herbicide flupyrsulfuron was applied post‐emergence in March at the rate of 10 g a.i. ha−1 on winter wheat crops. In the 0–8 cm surface soil layer of the crops grown on sandy loam and loam soils, the flupyrsulfuron half‐life was 64 and 40 days respectively. Flupyrsulfuron and its metabolites were not detected during both crops or 1 month after crop harvest in the 8–15 and 15–20 cm soil layers. Soil degradation of flupyrsulfuron successively generated the cyclization products 1‐(4,6‐dimethoxypyrimidine‐2‐yl)‐2,4‐diketo‐7‐trifluoromethyl‐1,2,3,4‐tetrahydropyrido[2,3‐d]pyrimidine 2 and N‐(4,6‐dimethoxypyrimidine‐2‐yl)‐N‐(3‐methoxycarbonyl‐6‐trifluoromethylpyridine‐2‐yl)‐amine 3, which were the main metabolites of flupyrsulfuron in soil. Hydrolysis of 3 successively generated N‐(4,6‐dimethoxypyrimidine‐2‐yl)‐N‐(3‐car‐ boxylic acid‐6‐trifluoromethylpyridine‐2‐yl)‐amine 4 and N‐(4‐methoxy‐6‐hydroxypyrimidine‐2‐yl)‐N‐(3‐carboxylic acid‐6‐trifluoromethylpyridine‐2‐yl)‐amine 5. Low and temporary concentrations of 2‐sulfonamido‐3‐carbomethoxy‐6‐trifluoromethyl‐pyridine 6 and 2‐amino‐4,6‐dimethoxypyrimidine 7 were observed. Bioassays with sugarbeet as test plants indicated that 2, 3, 4, 5, 6 and 7 had herbicide activities corresponding to 100%, 80%, 75%, 75%, 75% and 15% of that of flupyrsulfuron respectively. The metabolites thus extended the herbicidal protection given by flupyrsulfuron and explain the high herbicidal protection given by the low dose of flupyrsulfuron applied. One month after the harvest of the winter wheat, no more significant residue of flupyrsulfuron or of its metabolites was detected in soil.

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Section: Introductionmentioning

confidence: 99%

Soil metabolism of flupyrsulfuron in winter wheat crops

Rouchaud¹,

Moulard²,

Eelen³

et al. 2002

Weed Research

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“…Furthermore, crude extracts of wheat demonstrated GST activities towards fenoxapropethyl, fluorodifen, and metolachlor and these activities were enhanced by safener treatment (Edwards and Cole 1996). Recently, Koeppe et al (1998) reported that the initial metabolic pathway of flupyrsulfuron-methyl in wheat essentially involves GSH conjugation.…”

Section: Introductionmentioning

confidence: 99%

Purification and characterization of a safener‐induced glutathione S‐transferase from wheat (Triticum aestivum)

Pascal¹,

Scalla²

1999

Physiologia Plantarum

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The genome of cultivated wheat is hexaploid, and in consequence a large number of glutathione S‐transferase (GSTs, EC 2.5.1.18) isozymes is expected in that organism. Wheat GST subunits were first analyzed by reverse‐phase high performance liquid chromatography (RP‐HPLC). In root and shoot tissues, subunits 4, 8, and 9 were constitutively expressed whereas subunits 2, 3, and 5 were inducible by the herbicide safener naphthalic anhydride (NA). Significant differences were observed, however, between the distributions of these six major subunits in roots and shoots. A major GST isozyme was purified from the shoots of plants treated by NA. A combination of ammonium sulphate precipitation, hydrophobic interaction chromatography (HIC) and affinity chromatography resulted in purification with an apparent yield of 4.6% and a 48‐fold increase in specific activity toward 1‐chloro‐2,4‐dinitrobenzene (CDNB). Analysis by sodium dodecyl sulfate‐polyacrylamide gel electrophoresis (SDS‐PAGE) showed a single band at 24.5 kDa. Molecular mass estimated by nondenaturing PAGE was 49.5 kDa. These results suggest that the enzyme exists as a dimer. A pI of 5.2 was determined by native isoelectric focusing (IEF). Analysis by 2‐D electrophoresis showed a single spot, with a pI of 5.8–5.9. However, further analysis by RP‐HPLC revealed that the two subunits were different. They were characterized and identified by electrospray ionization mass spectrometry (ESI‐MS) as subunits 2 and 3, molecular masses 24 924±3 and 24 958±5 Da, respectively. Therefore, GST(2–3) is apparently a heterodimer consisting of subunits 2 and 3. Apparent KM values were 424 μM for CDNB and 228 μM for glutathione (GSH). GST(2–3) metabolized the herbicide fluorodifen, and a KM of 22 μM was determined for the herbicide.

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“…This result indicates the ALS enzyme of the oat plants is sensitive to iodosulfuron-methyl herbicide. On the literature, wheat (Triticum aestivum) plants tolerant to ALS inhibitors have shown similar ALS enzyme sensitivity to the herbicides, indicating that another mechanism is likely to be involved on the tolerance to the chemical (Koeppe et al, 1997).…”

Section: Identification Of Tolerance Mechanismsmentioning

confidence: 99%

Selectivity of Iodosulfuron-Methyl to Oat Cultivars

et al. 2017

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-Weeds are among the main constraints to high grain yield on hexaploid oat (Avena sativa), but there are few herbicides registered for weed control on this cereal crop. The objectives of this study were to evaluate the impact of the iodosulfuron-methyl on grain yield of elite oat cultivars and investigate the mechanism of oat tolerance to this herbicide. A field experiment conducted in 2012 demonstrated there was no difference on grain yield between cultivars URS Guará and URS Guria, when iodosulfuron-methyl was used up to 4.5 g ha , did not affect the oat grain yield of the genotype UFRGS 14, but affected it on the cultivars URS Guará and URS Guria. In 2014, the oat grain yield of five cultivars, including URS Guará, URS Guria and UFRGS 14 was reduced by iodosulfuron-methyl even at only 2.5 g ha -1. The activity of the ALS enzyme, extracted from oat plants, was sensitive to iodosulfuron-methyl. The increment of the iodosulfuron-methyl effect on oat plants treated with herbicide-detoxification inhibitors (malathion + chlorpyrifos), or the reduction of the herbicide efficacy in plants sprayed with the stimulator of detoxification (mefenpyr-diethyl), suggest that iodosulfuron-methyl degradation is the mechanism involved on its selectivity to oat plants.Keywords: Avena sativa, detoxification, tolerance, acetolactate synthase inhibitor. RESUMO -As plantas daninhas estão entre os principais problemas para o alto rendimento de grãos em aveia hexaploide (Avena sativa), mas existem poucos herbicidas registrados para o controle de plantas daninhas nessa cultura de cereais. Os objetivos deste estudo foram avaliar o impacto do iodosulfuron-methyl no rendimento de grãos de cultivares de aveia elite e investigar o mecanismo de

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Basis of Selectivity of the Herbicide Flupyrsulfuron-methyl in Wheat

Cited by 22 publications

References 6 publications

Soil metabolism of flupyrsulfuron in winter wheat crops

Soil metabolism of flupyrsulfuron in winter wheat crops

Purification and characterization of a safener‐induced glutathione S‐transferase from wheat (Triticum aestivum)

Selectivity of Iodosulfuron-Methyl to Oat Cultivars

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