Tribenuron

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Tribenuron methyl
File:Tribenuron methyl.svg
Names
IUPAC name
Methyl 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-methylcarbamoyl]sulfamoyl]benzoate
Other names
DPX L5300
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
EC Number
  • 401-190-1
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
KEGG
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C15H17N5O6S/c1-9-16-13(18-14(17-9)26-4)20(2)15(22)19-27(23,24)11-8-6-5-7-10(11)12(21)25-3/h5-8H,1-4H3,(H,19,22)
    Key: VLCQZHSMCYCDJL-UHFFFAOYSA-N
  • CC1=NC(=NC(=N1)OC)N(C)C(=O)NS(=O)(=O)C2=CC=CC=C2C(=O)OC
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
Hazards
GHS labelling:[1]
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Warning
H317, H373, H410
P260, P261, P272, P273, P280, P302+P352, P319, P321, P333+P317, P362+P364, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tribenuron in the form of tribenuron-methyl is a sulfonylurea herbicide.[2] Its mode of action is the inhibition of acetolactate synthase, Group 2 / Group B of the Herbicide Resistance Action Committee's classification scheme.[3][4]

Chemistry

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In the 1970s, chemists at DuPont worked extensively on sulfonylurea herbicides, following the invention of this class of herbicides by George Levitt which had led to the commercialisation of chlorsulfuron.[5] Tribenuron (the carboxylic acid) and its methyl ester[6] were first disclosed in general terms in one of Levitt's patents[7] and subsequently the ester was subject to further patenting[8] and selected for development under the code name DPX L5300.[1] In the final step of its synthesis, 2-methoxycarbonylbenzenesulfonyl isocyanate was condensed with 2-methylamino-4-methoxy-6-methyl-1,3,5-triazine to form the sulfonylurea product.[8]

File:Tribenuron synthesis.svg

Mode of action

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Tribenuron is an herbicide that acts as an acetolactate synthase inhibitor.[2][3] For the purposes of herbicide resistance management, the Herbicide Resistance Action Committee has placed it in group 2 (legacy HRAC Group B).[4]

Applications

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File:Tribenuron usage USA.png
US Geological Survey estimate of tribenuron methyl use in the USA to 2018

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

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In a clay-water suspension, tribenuron has increased sorption with decreasing pH and even more so with suspended load.[11]

Resistant crops

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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 oilseed type sunflower cultivars have been produced by USDA-ARS by conventional breeding.[13]

References

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  6. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  7. ^ US patent 4383113, George Levitt, "Agricultural sulfonamides", issued Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to E. I. du Pont de Nemours and Company 
  8. ^ a b US patent 4740234, Gerald E. Lepone, "Herbicidal ortho-carbomethoxysulfonylureas", issued Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to E. I. du Pont de Nemours and Company 
  9. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  10. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  11. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). p. 248.
  12. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  13. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).

Further reading

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  • Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). Supplemental.
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