| Identification | More | [Name]
Rimsulfuron | [CAS]
122931-48-0 | [Synonyms]
1-(4,6-DIMETHOXY-2-PYRIMIDINYL)-3-[3-(ETHYLSULFONYL)-2-PYRIDYLSULFONYL]UREA
DPX-E9636
Dupont E9636
n-(((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)-3-(ethylsulfonyl)-2-pyridinesulfonamide
RIMSULFURON
TITUS
1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-ethylsulfonyl-2-pyridylsulfonyl)urea
2-pyridinesulfonamide,n-(((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)-3-(ethy
lsulfonyl)-
n-(((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)-3-(ethylsulfonyl)-2-pyridin
n-(((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)-3-(ethylsulfonyl)-2-pyridinesulfonamid
RIMSULFURO
1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-ethylsulfonyl-2-pryidylsulfonyl)urea
RIMSULFURON PESTANAL, 100 MG
RIMSULPHURON
Totis
3-(4,6-Dimethoxypyrimidin-2-yl)-1-(3-ethylsulfonylpyridin-2-yl)sulfonylurea | [Molecular Formula]
C14H17N5O7S2 | [MDL Number]
MFCD01632305 | [Molecular Weight]
431.44 | [MOL File]
122931-48-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
172-177°C | [density ]
1.4918 (rough estimate) | [refractive index ]
1.6460 (estimate) | [Fp ]
>200 °C | [storage temp. ]
0-6°C | [solubility ]
DMSO (Slightly), Methanol (Very Slightly, Heated) | [form ]
neat | [pka]
4.1(at 25℃) | [color ]
White to Pale Beige | [BRN ]
7501778 | [Henry's Law Constant]
1.5×104 mol/(m3Pa) at 25℃, HSDB (2015) | [Major Application]
agriculture
environmental | [InChI]
InChI=1S/C14H17N5O7S2/c1-4-27(21,22)9-6-5-7-15-12(9)28(23,24)19-14(20)18-13-16-10(25-2)8-11(17-13)26-3/h5-8H,4H2,1-3H3,(H2,16,17,18,19,20) | [InChIKey]
MEFOUWRMVYJCQC-UHFFFAOYSA-N | [SMILES]
C1(S(NC(NC2=NC(OC)=CC(OC)=N2)=O)(=O)=O)=NC=CC=C1S(CC)(=O)=O | [CAS DataBase Reference]
122931-48-0(CAS DataBase Reference) | [EPA Substance Registry System]
122931-48-0(EPA Substance) |
| Questions And Answer | Back Directory | [Description]
Rimsulfuron is an herbicide for the treatment of annual broadleaf weeds, certain grasses and perennial broadleaf weeds. It is quite effective in the treatment of glyphosate-resistant weed species such as marestail/horseweed. Its mechanism of action is through inhibiting the acetolactate synthase (ALS), which is involved in the synthesis of isoleucine, leucine and valine of plant, further blocking protein synthesis and the growth of weeds.
| [Reference]
- Rathinasabapathi, Bala. "Physiological Basis for Differential Tolerance of Tomato and Pepper to Rimsulfuron and Halosulfuron: Site of Action Study." Weed Science 52.2(2004):201-205.
- Schneiders, G. E., et al. "Fate of rimsulfuron in the environment. " Journal of Agricultural & Food Chemistry 41.12(1993): 2404-2410.
- Ackley, John A., and T. E. Hines. "Efficacy of Rimsulfuron and Metribuzin in Potato (Solanum tuberosum)." Weed Technology 10.3(1996):475-480.
- Koeppe, M. K., et al. "Basis of Selectivity of the Herbicide Rimsulfuron in Maize ☆." Pesticide Biochemistry & Physiology 66.3(2000):170-181.
|
| Hazard Information | Back Directory | [Uses]
Rimsulfuron is used as a pesticide. | [Definition]
ChEBI: A N-sulfonylurea that is N-carbamoyl-3-(ethylsulfonyl)pyridine-2-sulfonamide substituted by a 4,6-dimethoxypyrimidin-2-yl group at the amino nitrogen atom. | [Production Methods]
Rimsulfuron is commercially produced via a convergent multi-step synthesis: the sulfonamide intermediate N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(ethylsulfonyl)pyridine-3-sulfonamide is formed by coupling 2-amino-4,6-dimethoxypyrimidine with 2-(ethylsulfonyl)pyridine-3-sulfonyl isocyanate (generated from 2-(ethylthio)pyridine-3-sulfonamide via phosgene or triphosgene activation followed by oxidation with hydrogen peroxide); subsequent condensation with dimethylamine or direct amination yields the active substance. | [Agricultural Uses]
Herbicide: For controlling broadleaf weeds. Registered for use in the U.S. and Canada. A U.S. EPA restricted Use Pesticide (RUP) for some formulations. Registered for use in some EU countries. | [Trade name]
ACCENT®; BASIS® (rimsulfuron+thifensulfuron methyl); DPX-E9636®; DPX 79406® (nicosulfuron+rimsulfuron); Matrix® (nicosulfuron+rimsulfuron); SHADEOUT®; STEADFAST®, (nicosulfuron+rimsulfuron); TRANXIT® | [Mechanism of action]
Selective, systemic, absorbed through foliage and roots and translocated.Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS | [Metabolic pathway]
The primary degradation pathway in most of the
systems examined is the contraction or
rearrangement and hydrolysis of the sulfonylurea
linkage to yield two products that have N-pyridyl-N-
pyrimidyl urea and N-pyridyl-N-pyrimidylamine
moieties, and fragments of pyridine sulfonamide, 4,6-
dimethoxy-2-pyrimidylurea, and 4,6-dimethoxy-2-
amino-pyrimidine, respectively. In plants,
demethylation and hydroxylation reactions follow the contraction or rearrangement to give N-3,4-dihydroxy-
5-methoxy-2-pyrimidyl-N(3-ethylsulfonyl-2-
pyridyl)amine. | [storage]
Store at -20°C | [Pesticide Type]
Herbicide |
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