Tribenuron
Names | |
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IUPAC name
Methyl 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-methylcarbamoyl]sulfamoyl]benzoate
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Other names
DPX L5300
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Identifiers | |
3D model (
JSmol ) |
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ECHA InfoCard
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100.100.313 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties[1] | |
C15H17N5O6S | |
Molar mass | 395.39 g·mol−1 |
Appearance | White to off-white solid |
Density | 1.46 g/cm3 |
Melting point | 142 |
2483 mg/L (20 °C) | |
log P | 0.38 |
Acidity (pKa) | 4.65 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tribenuron in the form of tribenuron-methyl is a
Chemistry
In the 1970s, chemists at
Mode of action
Tribenuron is an
Applications
Tribenuron has a broad spectrum of activity on commercially important broadleaf weeds and grasses but at the recommended use rate it is safe to important crops such as wheat. When introduced by DuPont, its recommended application rate was 0.015–0.03 pounds per acre (17–34 g/ha).[9] The estimated use in US agriculture is mapped by the US Geological Service and shows that from 1992 to 2018, up to 120,000 pounds (54,000 kg) were applied each year. The compound is used mainly in wheat but also in pasture.[10]
Physicochemistry
In a clay-water suspension, tribenuron has increased sorption with decreasing pH and even more so with suspended load.[11]
Resistant crops
A tribenuron-resistance transformation has been achieved in watermelon and validated by survival of the als mutants but not the controls, under tribenuron treatment.[12]
Two
References
- ^ a b Pesticide Properties Database. "Tribenuron-methyl". University of Hertfordshire.
- ^ Herbicide Resistance Action Committee (HRAC) (2 June 2020). "Global HRAC MOA Classification Working Group Report"(PDF).
- ^ a b Scott Senseman (3 December 2020). "Weed Science Society of America - Herbicide Site of Action (SOA) Classification List".
- ^ Herbicide Resistance Action Committee(HRAC). 11 March 2020.
- ^ Bhardwaj, Gaurab (2007). "From Pioneering Invention to Sustained Innovation: The Story of Sulfonylurea Herbicides" (PDF). Chemical Heritage NewsMagazine. 25 (1). Archived from the original (PDF) on 2006-11-18.
- S2CID 198130304.
- ^ US patent 4383113, George Levitt, "Agricultural sulfonamides", issued 1983-05-10, assigned to E. I. du Pont de Nemours and Company
- ^ a b US patent 4740234, Gerald E. Lepone, "Herbicidal ortho-carbomethoxysulfonylureas", issued 1988-04-26, assigned to E. I. du Pont de Nemours and Company
- ^ DuPont (2004). "DuPont Tribenuron Methyl 50SG" (PDF).
- ^ US Geological Survey. "Estimated Agricultural Use for tribenuron methyl, 2018". Retrieved 2023-01-13.
- PMID 1580364. p. 248.
- PMID 31240102.
- S2CID 85001003.
Further reading
- Kreiner, Julia M.; Stinchcombe, John R.; Wright, Stephen I. (2018-04-29). "Population Genomics of Herbicide Resistance: Adaptation via Evolutionary Rescue". S2CID 25489201. Supplemental.