Oxasulfuron Chemical Properties

Melting point:

158°C (decomposition)

Density 

1.49±0.1 g/cm3(Predicted)

solubility 

Solubility in organic solvents (g/l at 25 °C)
Acetone 9.3
Ethyl acetate 2.3
Dichloromethane 69.0
n-Hexane 0.0022
Toluene 0.32

pka

Dissociation constant (pKa) 5.10

Water Solubility 

Solubility in water (g/l at 25 °C)
0.052 (pH 5.1)
0.063 (pH 5.0, buffer solution)
1.70 (pH 6.8, buffer solution)
19.0 (pH 7.8, buffer solution)

Major Application

agriculture
environmental

InChI

1S/C17H18N4O6S/c1-10-7-11(2)19-16(18-10)20-17(23)21-28(24,25)14-6-4-3-5-13(14)15(22)27-12-8-26-9-12/h3-7,12H,8-9H2,1-2H3,(H2,18,19,20,21,23)

InChIKey

IOXAXYHXMLCCJJ-UHFFFAOYSA-N

SMILES

Cc1cc(C)nc(NC(=O)NS(=O)(=O)c2ccccc2C(=O)OC3COC3)n1

CAS DataBase Reference

144651-06-9(CAS DataBase Reference)

EPA Substance Registry System

Oxasulfuron (144651-06-9)

Safety Information

Hazard Codes 

Xn;N,N,Xn

Risk Statements 

48/22-50/53

Safety Statements 

46-60-61

RIDADR 

UN 3077

WGK Germany 

3

HS Code 

29350090

Storage Class

11 - Combustible Solids

Hazard Classifications

Aquatic Acute 1
Aquatic Chronic 1
STOT RE 2

Oxasulfuron Usage And Synthesis

Uses

Oxasulfuron is used in liquid sulfonylurea herbicide composition.

Agricultural Uses

Oxasulfuron (CGA 277476) was launched in 1996 by Syngenta as a pre-emergent and post-emergent herbicide. At application rates of 66–92 g a.i. ha−1, it provides greater than 80% control of A theophrasti, X. strumarium, Amaranthus spp., A. artemisiifolia, A. trifida, Bidens pilosa, Cyperus esculentus, Polygonum pensylvanicum, Sorghum bicolor, E. crus‐galli, Helianthus annuus, Sesbania exaltata, and Ipomoea spp. in soybeans. The observed selectivity is due to the compound’s rapid metabolization in the target crop.

Synthesis

Oxasulfuron is commercially prepared through a multi-step synthesis involving sulfonylurea formation and esterification. It begins with the preparation of a sulfonylurea intermediate, typically derived from 4,6-dimethyl-2-aminopyrimidine and sulfonyl isocyanate or related reagents. This intermediate is then coupled with 2-carboxybenzenesulfonyl chloride to form the sulfonylurea linkage. The resulting compound undergoes esterification with oxetan-3-ol, introducing the oxetanyl ester group that enhances herbicidal activity and environmental stability.

Oxasulfuron(144651-06-9)Related Product Information

• Sulfometuron-methyl
• CYCLOPENTANESULFONYL CHLORIDE
• 4,6-Dimethoxypyrimidine
• o-Ethoxycarbonylbenzenesulfonamide
• Oxetan-3-ol
• 2-Carbomethoxybenzenesulfonamide
• 2-CARBOXY PHENYLSULFAMIDE
• Oxasulfuron
• ETHYL O-THIOSALICYLATE