Degradation and Mobility of Sulfometuron-methyl (Oust Herbicide) in Field Soil

Trubey, Richard K.; Bethem, Robert A.; Peterson, Bob

doi:10.1021/jf970745x

Cited by 26 publications

(18 citation statements)

References 7 publications

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“…This cyclization degradation pathway that generated compound 2 is unusual with the sulphonylurea herbicides. It was not observed with the sulphonylureas benzene–triazine metsulfuron and the benzene–pyrimidine sulfometuron, in spite of the carbomethoxy group on the benzene ring in ortho to the sulfonylurea bridge (Anderson et al ., 1989; Trubey et al ., 1998).…”

Section: Resultsmentioning

confidence: 99%

“…Metabolite 3 was generated by bridge contraction, in the same way as the pyridine–pyrimidine rimsulfuron in soil (Schneiders et al ., 1993; Rouchaud et al ., 1997). The benzene–triazine sulfonylureas metsulfuron in wheat and sulfometuron in soil, and the thiophene–triazine sulfonylurea thifensulfuron in soil did not, however, generate the corresponding amine by bridge contraction (Anderson et al ., 1989; Cambon et al ., 1998; Trubey et al ., 1998).…”

Section: Resultsmentioning

confidence: 99%

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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: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Soil metabolism of flupyrsulfuron in winter wheat crops

Rouchaud¹,

Moulard²,

Eelen³

et al. 2002

Weed Research

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“…Trubey et al 8 have reported that sulfometuron-methyl underwent the cleavage of sulfonylurea bond under aerobic upland conditions. From these findings, it was assumed that imazosulfuron in upland soils underwent the hydrolysis of sulfonylurea bond to give ADPM and IPSN.…”

Section: Discussionmentioning

confidence: 99%

Degradation and Leaching of Herbicide Imazosulfuron in Upland Soils

2001

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Degradation of imazosulfuron in upland soils was investigated under laboratory conditions using two kinds of 14C labeled imazosulfuron. Imazosulfuron degraded with half-life of approximately 40 days, and the major degradation pathway was the hydrolysis of the sulfonylurea bond to give ADPM and IPSN. The leaching studies of imazosulfuron using non-aged and aged soils were also conducted. It was found that imazosulfuron was less mobile in soils when the soil column was eluted with 0. 02 N CaC12 solution after 30 days of aging period of time compared to non-aging. Main degradation products, ADPM and IPSN, were adsorbed in soils stronger than imazosulfuron.It was suggested that imazosulfuron dissipates relatively fast in upland soils, and the leaching potential decreases with time.

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“…The aqueous layer was extracted with ether (2x75 ml), and the organic fractions were combined, not dried, filtered, evaporated, and recrystallized to afford product. [2][3]4,)benzenesulfonamide (4a).…”

Section: Methodsmentioning

confidence: 99%