| Identification | Back Directory | [Name]
Orthosulfamuron | [CAS]
213464-77-8 | [Synonyms]
famuron
OrthosuL
ORTHOSULFAMURON
Orthosulfamuron [iso]
Orthosulfamuron solution
Orthosulfamuron@100 μg/mL in Acetone
1-(4,6-Dimethoxypyrimidin-2-yl)-3-[2-(dimethylcarbamoyl)phenylsulfamoyl]urea
2-((N-((4,6-Dimethoxypyrimidin-2-yl)carbamoyl)sulfamoyl)amino)-N,N-dimethylbenzamide
Benzamide, 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]amino]-N,N-dimethyl- | [EINECS(EC#)]
606-744-8 | [Molecular Formula]
C16H20N6O6S | [MDL Number]
MFCD09027340 | [MOL File]
213464-77-8.mol | [Molecular Weight]
424.436 |
| Chemical Properties | Back Directory | [Melting point ]
160–162°C | [density ]
1.466±0.06 g/cm3(Predicted) | [vapor pressure ]
<1.1 × 10?4 (Pa at 25 °C) | [storage temp. ]
Refrigerator, under inert atmosphere | [solubility ]
Solubility in organic solvents (g/l at 20 °C)
Acetone 20
Ethyl acetate 3.3
Dichloromethane 56
n‐Heptane 0.00023
Methanol 8.3
Xylene 0.13 | [form ]
neat | [pka]
Dissociation constant (pKa at 20 °C) Predicted to have five overlapping dissociation constants: ?1.4, 0.7, 3.5, 9.6, 11.5 | [color ]
White to Off-White | [Water Solubility ]
Solubility in water (g/l at 20 °C) 0.026 (pH 4, buffer) 0.63 (pH 7, buffer) 39 (pH 8.5, buffer) | [BRN ]
11343666 | [Henry's Law Constant]
1.3×104 mol/(m3Pa) at 25℃, HSDB (2015) | [Stability:]
Moisture Sensitive | [Major Application]
agriculture
environmental | [InChI]
1S/C16H20N6O6S/c1-22(2)14(23)10-7-5-6-8-11(10)20-29(25,26)21-16(24)19-15-17-12(27-3)9-13(18-15)28-4/h5-9,20H,1-4H3,(H2,17,18,19,21,24) | [InChIKey]
UCDPMNSCCRBWIC-UHFFFAOYSA-N | [SMILES]
COc1cc(OC)nc(NC(=O)NS(=O)(=O)Nc2ccccc2C(=O)N(C)C)n1 | [LogP]
0.3-2.02 at 20℃ and pH4-9 | [Surface tension]
71.4mN/m at 37.7mg/L and 22℃ | [EPA Substance Registry System]
Benzamide, 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]amino]-N,N-dimethyl- (213464-77-8) |
| Hazard Information | Back Directory | [Description]
A herbicide used to control weeds, especially sedges, in rice. It is moderately soluble in water, volatile and, based on its chemical properties, there is a high risk of of leaching to groundwater. It tends not to be persistent in either soil or aquatic systems. It has a low mammalian toxicity and not thought to bioaccumulate. However, there are some concerns that it may be neurotoxic and be a reproduction/development toxin. It has a low to moderate toxicity to most biodiversity. | [Uses]
Orthosulfamuron can be used in biological study and agricultural use of herbicidal composition comprising erlukuilincaotong, cyhalofop-?butyl and sulfonylurea herbicide, and its application in controlling annual weed of rice field. | [Definition]
ChEBI: Orthosulfamuron is an N-sulfonylurea and sulfuric amide resulting from the formal condensation of sulfuric acid with the primary amino group of 1-(4,6-dimethoxypyrimidin-2-yl)urea and with the primary amino group of 2-amino-N,N-dimethylbenzamide (1 mol eq. of each). An acetolactate synthase inhibitor, it is used as a pre- and post-emergent herbicide for the treatment of grasses and broad-leaved weeds in rice crops. It has a role as an EC 2.2.1.6 (acetolactate synthase) inhibitor and a herbicide. It is a tertiary carboxamide, a sulfuric amide, a N-sulfonylurea and an aromatic ether. | [Production Methods]
Orthosulfamuron is synthesised through a multi-step process beginning with anthranilic acid and 2-amino-4,6-dimethoxypyrimidine as the core starting materials. First, anthranilic acid reacts with phosgene in tetrahydrofuran at low temperature to form isatoic anhydride. This intermediate is then treated with dimethylamine to yield 2-amino-N,N-dimethylphenylamide. Separately, 2-amino-4,6-dimethoxypyrimidine reacts with sulfonyl chloride isocyanate in dichloromethane to produce a sulfonyl chloride derivative. Finally, this reactive intermediate is coupled with the dimethylphenylamide in the presence of triethylamine, forming orthosulfamuron as the final product. | [Agricultural Uses]
Orthosulfamuron (IR‐5878, CAS no.: 213464-77-8) is a broad‐spectrum pre‐ and post‐emergent rice herbicide developed by Isagro for the control of annual broadleaf and sedge weeds. It was sold in 2013 to Nihon Nohyaku Co., Ltd. and can be used also for sugarcane ripening.
The compound has been marketed since 2007 under the trade names “Kelion® 50 WG,” “Strada® WG,” and “Pivot® 50 WG” for early and middle post‐emergence application against susceptible weeds and sedges, such as A. theophrasti, Alisma plantago‐aquatica, A. lanceolatum, C. difformis, C. serotinus, Cyperus ferax, Cyperus iria, E. crus‐galli (red biotype), Heteranthera reniformis, Heteranthera rotundifolia, H. limosa, L. dubia, Schoenoplectus mucronatus, Bolboschoenus maritimus, Sagittaria sagittifolia, and Scirpus supinus at a use rate of 40–75 g a.i. ha−1. | [Mechanism of action]
Systemic, systemic absorbed by foliage and roots and translocated, acetohydroxy acid synthase | [Pesticide Type]
Herbicide |
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