| Identification | Back Directory | [Name]
Procarbazone sodium | [CAS]
181274-15-7 | [Synonyms]
UK 657
MK 6561
OLYMPUS
ATTRIBUT
MKH 6561
procarbazone
Bay MKH 6561
Procarbazone sodium
PROPOXYCARBAZONE SODIUM
PROPOXYCARBAZONE SODIUM SALT
1-propoxycarbazone, sodiuM salt
propoxycarbazone sodium(bsi,iso)
Propoxycarbazone Sodium salt, Pestanal
2-[(4-methyl-5-oxo-3-propoxy-1,2,4-triazolin-1-yl)carbamidosulfonyl]benzoic acid methyl ester sodium salt
2-[(4-METHYL-5-OXO-3-PROPOXY-1,2,4-TRIAZOLIN-1-YL)CARBAMIDOSULFONYL]BENZOIC ACID METHYL ESTER SODIUM SALT
methyl-2-(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl) carboxamideo sulfonylbenzoate sodium salt
Methyl 2-((((4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl)carbonyl)amino)sulfonyl)benzoate sodium salt
methyl 2-((((4,5-dihydro-4-methyl-5-oxo-3-propoxy-1h-1,2,4-triazol-1-yl)carbonyl)amino)sulfonyl)benzoate sodium salt
Sodium {[2-(methoxycarbonyl)phenyl]sulfonyl}[(4-methyl-5-oxo-3-propoxy-4,5-dihydro-1H-1,2,4-triazol-1-yl)carbonyl]azanide | [Molecular Formula]
C15H17N4NaO7S | [MDL Number]
MFCD04112619 | [MOL File]
181274-15-7.mol | [Molecular Weight]
420.37 |
| Chemical Properties | Back Directory | [Melting point ]
230–240°C (under decomposition) | [storage temp. ]
0-6°C | [solubility ]
Solubilities in organic solvents (g/l at 20 °C) Dimethylsulfoxide: 190 Poly(ethylene glycol): 5.2 Acetonitrile: 0.9 2‐Propanol: <0.1 Xylene: <0.1 | [form ]
neat | [pka]
The free acid produced by protonation under acidic conditions has a pKa of 2.1 (at 20 °C) | [Water Solubility ]
Solubility in water (at 20 °C) : Unbuffered water and buffered between pH 7 and 9: 42 g/l. Solubility is not influenced by pH in the range pH 7-9. Solubility at pH 4.5: 2.9 g/l | [Henry's Law Constant]
1.0×1010 mol/(m3Pa) at 25℃, Maniere et al. (2011) | [Stability:]
Hygroscopic | [InChI]
InChI=1S/C15H18N4O7S.Na/c1-4-9-26-14-16-19(15(22)18(14)2)13(21)17-27(23,24)11-8-6-5-7-10(11)12(20)25-3;/h5-8H,4,9H2,1-3H3,(H,17,21);/q;+1/p-1 | [InChIKey]
JRQGDDUXDKCWRF-UHFFFAOYSA-M | [SMILES]
N1(N=C(OCCC)N(C)C1=O)C(=O)N([Na])S(=O)(=O)C1=CC=CC=C1C(OC)=O | [CAS DataBase Reference]
181274-15-7 | [EPA Substance Registry System]
Benzoic acid, 2-[[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl)carbonyl]amino] sulfonyl]-, methyl ester, sodium salt(181274-15-7) |
| Safety Data | Back Directory | [Hazard Codes ]
N | [Risk Statements ]
50/53 | [Safety Statements ]
60-61 | [RIDADR ]
UN3077 9/PG 3 | [WGK Germany ]
2 | [Hazardous Substances Data]
181274-15-7(Hazardous Substances Data) | [Toxicity]
LD50 in rats (mg/kg): >5000 orally; >5000 dermally; LC50 in rats (mg/m3): >5030 in air by inhalation; LC50 (96 hr) in bluegill sunfish, rainbow trout (mg/l): >94.7; >77.6 (Feucht) |
| Hazard Information | Back Directory | [Description]
Propoxycarbazone-sodium is a post-emergence trazolone herbicide. It is highly soluble in water and mobile in soils and so has a high tendency to leach to groundwater. It is semi-volatile and is not persistent in soil. However, it is persistent in aquatic systems. It has a low oral toxicity and there are no serious human health risks reported. It is moderately toxic to birds, earthworms and fish. Its toxicity to honeybees is low. | [Chemical Properties]
The pure product is a colorless, odorless powdery crystal. Its mp is 230-240°C, with decomposition occurring during melting. Its relative density is 1.42 (20°C), its vapor pressure is <1×10-8 Pa (20°C), and its partition coefficients are -0.30 (pH=4.0), -1.55 (pH=7.0), and -1.59 (pH=9.0). Its solubility at 20°C is 1.50 g/L in dichloromethane, <0.1 g/L in n-heptane, <0.1 g/L in xylene, <0.1 g/L in isopropyl alcohol, and 42 g/L (pH=7-9) and 2.9 g/L (pH=4.5) in water. It is stable in air at room temperature and readily degrades in soil, with a half-life of 9 days. | [Uses]
Herbicide. | [Production Methods]
Propoxycarbazone-sodium is commercially produced via a multi-step synthesis starting from 2-amino-4,6-dimethoxypyrimidine, which is sulfonylated with 2-(chlorosulfonyl)benzoic acid methyl ester in the presence of pyridine or triethylamine in dichloromethane to form the sulfonamide intermediate. This is coupled with propyl chloroformate in acetone using potassium carbonate to yield the carbamate-protected sulfonylurea precursor. Cyclisation to the triazolone ring is achieved by reaction with hydrazine hydrate in ethanol under reflux, followed by oxidation with iodine or air to close the ring and form propoxycarbazone acid. Final neutralisation with sodium hydroxide in aqueous methanol and crystallization from isopropanol-water produces propoxycarbazone-sodium. | [Mechanism of action]
Absorbed by leaves and roots and translocated. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS. | [Pesticide Type]
Herbicide |
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