Procarbazone sodium
Procarbazone sodium
CAS: 181274-15-7
Molecular Formula: C15H17N4NaO7S
Procarbazone sodium - Names and Identifiers
| Name | Procarbazone sodium |
| Synonyms | OLYMPUS MKH 6561 ATTRIBUT Procarbazone sodium PROPOXYCARBAZONE SODIUM PROPOXYCARBAZONE 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)carbonyl)amino)sulfonyl)benzoate sodium salt sodium N-{[2-(methoxycarbonyl)phenyl]sulfonyl}-4-methyl-5-oxo-3-propoxy-4,5-dihydro-1H-1,2,4-triazole-1-carboximidate Benzoic acid, 2-[[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazole-yl-)carbonyl] sulfonyl]-, methyl ester, sodium salt |
| CAS | 181274-15-7 |
| InChI | InChI=1/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 |
Procarbazone sodium - Physico-chemical Properties
| Molecular Formula | C15H17N4NaO7S |
| Molar Mass | 420.37 |
| Melting Point | 230-240° (dec) |
| Boling Point | 546°C at 760 mmHg |
| Flash Point | 284°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 |
| Solubility | Solubilities in organic solvents (g/l at 20 °C) Dimethylsulfoxide: 190 Poly(ethylene glycol): 5.2 Acetonitrile: 0.9 2‐Propanol: |
| Vapor Presure | 9.339999E-13mmHg at 25°C |
| Appearance | neat |
| pKa | The free acid produced by protonation under acidic conditions has a pKa of 2.1 (at 20 °C) |
| Storage Condition | 0-6°C |
| Physical and Chemical Properties | Storage Conditions: 0-6 ℃ |
Procarbazone sodium - Risk and Safety
| Hazard Symbols | N - Dangerous for the environment |
| Risk Codes | 50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN3077 9/PG 3 |
| WGK Germany | 2 |
| 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) |
Procarbazone sodium - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | propanuron is a new sulfonylurea herbicide developed by Bayer company in Germany, which rapidly depletes branched chain amino acids such as valine, leucine and isoleucine in weed cells, first affecting the synthesis of new proteins and finally stopping the growth of cells. The compound acts mainly through soil absorption. It is mainly used for post-seedling stem and leaf treatment to control gramineous weeds in cereal crops such as wheat, barley, and rye fields, including annual weeds and some perennial weeds such as oats, watching wheat Niang, and wind-cut stringes, Thatch, Goosegria, Abella grass, and the hard-to-remove broth grass, as well as some broad-leaved weeds, white chestnut, blue cabbage, etc. It has been registered in more than 20 countries and regions, including Belarus, Czech Republic, France, Germany, Kazakhstan, Poland, Sweden, Turkey and the United States. |
| synthesis | prophenylene sulfuron-methyl is mainly synthesized by the reaction of 4-methyl -5-propoxy-2, 4-dihydro-3H-1, 2, 4-triazol-3-one (hereinafter referred to as PMT) with methyl orthoformate benzenesulfonyl isocyanate (hereinafter referred to as BIM), and then prepared by salt reaction. The chemical reaction formula is as follows: using xylene as solvent, adding BIM dropwise to PMT solution at 25 ℃, after dropping, reacting at 40~45 ℃ for 6 h to generate 2-(4, 5-dihydro-4-methyl-5-keto-3-propoxy-1H-1, 2, 4-triazol-1-yl) formylaminosulfonylbenzoate methyl ester (hereinafter referred to as PSU), then alkalize it to obtain the target product propensulfuron. 83.3% yield. The pure product is white powder with melting point of 230~240 ℃. 1. Synthesis of intermediate 4-methyl -5-propoxy -2, 4-dihydro-3H-1, 2, 4-triazol-3-one (PMT) using ethyl hydrazinoformate as the starting material One raw material of this method is ethyl hydrazinoformate, and the other raw material is methyl imino-carbonate compounds. The catalyst is trimethylacetic acid and concentrated hydrochloric acid. The specific method is as follows: methyl iminomethyl thiocarbonic acid n-propyl ester method, the chemical reaction formula is as follows: ethyl hydrazinyl formate is dissolved in water, concentrated hydrochloric acid is used as catalyst, methyl iminomethyl thiocarbonic acid is added dropwise at 0 ℃, reaction is carried out under ice bath for 15h, 45% sodium hydroxide solution is added at 20 ℃, and reaction is carried out at 60 ℃ for 6h. The reaction solution is neutralized with hydrochloric acid in an ice bath, and then extracted with ethyl acetate for 3 times. The organic phase is taken, dried and concentrated to obtain PMT. 84% yield. The pure product is a colorless needle-like crystal with a melting point of 74°C. 2. Synthesis of intermediate methyl o-formate benzenesulfonyl isocyanate (BIM) Using methyl o-formate benzenesulfonamide as raw material oxalyl chloride method, the chemical reaction formula is as follows: toluene is used as solvent, triethylamine is used as catalyst, methyl o-formate benzenesulfonamide refluxes with oxalyl chloride under N2 protection for 5 h, and toluene is evaporated to obtain BIM. 75% yield. Boiling point 150 ℃/133.32 Pa. (2015-11-03) |
| toxicity | rat acute oral LD50>5000mg/kg, rat acute inhalation LC50 5030mg/L, no irritation to rabbit eyes, slight irritation to skin, no sensitization to guinea pig skin. There were no chronic and acute toxic reactions in birds and mammals. Acute oral LD50>2000mg/kg bw, LC50>10566mg/kg bw (5d). Rainbow trout LC50>77.2 mg/kg, sunfish 94.2 mg/kg, bee oral or contact LD50>319 μg/and> 200 μg/, earthworm LD50>1000 mg/kg soil (14d). |
| use | novel sulfonylurea herbicides, ALS inhibitors, make the branched chain amino acids such as valine, leucine and isoleucine in weed cells The rapid depletion of, first of all, affects the synthesis of new proteins, and finally stops the growth of cells until they wither. It is mainly used for post-seedling stem and leaf treatment to control gramineous weeds in cereal crops such as wheat, barley, and rye fields, including annual weeds and some perennial weeds such as oats, watch wheat Niang, and wind Cut stringes, thatch, goose grass, Abella grass and difficult to remove, as well as some broad-leaved weeds such as white chestnut and blue cabbage. The dosage is 28~70g active ingredient/hm2, and the spraying amount is 200~400L/hm2. In order to make full use of the soil activity of the active ingredients, it is best to use it when weeds just resume growth in early spring. In order to better control broadleaf weeds, it is also necessary to mix with other types of herbicides with different mechanisms of action. The selectivity of tribenuron-methyl is mainly based on the different degradation rates in wheat and sensitive weeds. |
| Production method | Using methyl thioisocyanate and n-propanol as starting materials, the intermediate triazolinone is prepared, and then the intermediate triazolinone is synthesized by reaction with sulfonyl isocyanate. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:04
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