[(4-Aminophenyl)sulfonyl]carbamic acid methyl ester
asulam
CAS: 3337-71-1
Molecular Formula: C8H10N2O4S
[(4-Aminophenyl)sulfonyl]carbamic acid methyl ester - Names and Identifiers
| Name | asulam |
| Synonyms | asulam Jonnix Asulox Asulon Asilan mb 9057 MB 9057 UPPERCUT Methyl sulfanilylcarbamate METHYL SULFANILYLCARBAMATE methyl sulphanilylcarbamate METHYL 4-AMINOPHENYLSULPHONYLCARBAMATE methyl ((4-aminophenyl)sulfonyl)carbamate Methyl [(4-aminophenyl)sulfonyl]carbamate [(4-Aminophenyl)sulfonyl]carbamic acid methyl ester |
| CAS | 3337-71-1 |
| EINECS | 222-077-1 |
| InChI | InChI=1/C8H10N2O4S/c1-14-8(11)10-15(12,13)7-4-2-6(9)3-5-7/h2-5H,9H2,1H3,(H,10,11) |
[(4-Aminophenyl)sulfonyl]carbamic acid methyl ester - Physico-chemical Properties
| Molecular Formula | C8H10N2O4S |
| Molar Mass | 230.24 |
| Density | 1.4655 (rough estimate) |
| Melting Point | 142-144°C (dec.) |
| Water Solubility | 5g/L(room temperature) |
| Solubility | DMSO (Slightly), Methanol (Slightly) |
| Appearance | neat |
| Color | Pale Brown to Light Brown |
| Merck | 13,862 |
| BRN | 2697523 |
| pKa | 4.82(at 25℃) |
| Storage Condition | 0-6°C |
| Refractive Index | 1.5690 (estimate) |
| Physical and Chemical Properties | Melting point 142-144°C (dec.) |
| Use | Is a selective inhalation of herbicides, cell growth inhibitors |
[(4-Aminophenyl)sulfonyl]carbamic acid methyl ester - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| WGK Germany | 3 |
| RTECS | FD1190000 |
| HS Code | 29350090 |
| Toxicity | LD50 in rats, mice, dogs, rabbits (mg/kg): >5000, >5000, >5000, >2000 orally; in rats (mg/kg): >1200 dermally (Brockelsby) |
[(4-Aminophenyl)sulfonyl]carbamic acid methyl ester - Upstream Downstream Industry
| Raw Materials | Sodium formate Dimethyl carbonate |
[(4-Aminophenyl)sulfonyl]carbamic acid methyl ester - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| herbicide | . Other names: Asulox, MB9057), is a carbamate selective absorption conduction type seedling herbicide, is a cell growth inhibitor. It was first reported by H. J. Cotton & B. J. It is mainly used in sugarcane, fir, turf, ornamental crops and non-crop fields. The dosage form is an aqueous agent. On June 28, 2022, the pesticide control Institute of the Ministry of Agriculture and Rural Affairs announced the list of the 5th batch of pesticide products to be approved for registration in 2022. Including Nantong Taihe Chemical Co., Ltd., 97% of the original sulfadiazine (only for export to Australia), which is the first domestic sulfadiadiadiene. |
| mechanism of action | sulfolin is a kind of carbamate herbicide with internal absorption conduction. The medicament is easily absorbed by the stem, leaf and root of the plant, and then can be rapidly transmitted to the growing point of the underground rhizome, and the respiration of the underground rhizome is inhibited, the reproductive ability is lost, and the cell division is hindered to cause the plant to die. Inhibition of folic acid synthesis results in a decrease in nucleic acid synthesis, which is the mechanism of action of the present agent. |
| toxicity | rat acute oral LD50>8000mg/kg, acute percutaneous LD50>1200mg/kg. Mouse acute oral ld5017540 mg/kg (male), acute percutaneous ld5015000 mg/kg. Potassium salt mice oral LD50>2000mg/kg, percutaneous LD50>500mg/kg. Has a slight irritating effect on the skin. Feeding rats with 400 mg/kg sodium salt for 90 days had no obvious effect. Rainbow trout LC50>5000mg/L (96H). Low toxicity to birds, quails acute oral LD50>2000mg/kg. Non-toxic to bees. |
| Use | systemic sulfonamide herbicide. The medicament is easily absorbed by the stem, leaf and root of the plant, and then can be rapidly transmitted to the growing point of the underground rhizome, and the respiration of the underground rhizome is inhibited, the reproductive ability is lost, and the cell division is hindered to cause the plant to die. Inhibition of folic acid synthesis results in a decrease in nucleic acid synthesis, which is the mechanism of action of the present agent. Low temperature and air drying, is not conducive to the penetration and conduction of the agent. When the temperature is 25~30 ℃ and the relative humidity is high, it is beneficial to the penetration and conduction of the medicament into the plant. It is generally used for sugarcane, grass, flax, potato, cotton and tea garden, deciduous Orchard, to control annual and perennial weeds, such as motherwort, Wild Oats, Kentucky bluegrass, Rumex, Matsuya, Shitao, corn gluten, gold, paspalle, storage, Sonchus, elaeagnus, Etc., also have certain control effect on cutting stock, dog Bud-eye, Field Thistle, dandelion, euphorbiae, etc, portulaca oleracea, aconite and Portulaca oleracea were ineffective. If the sugarcane field is herbicidal, the plant height should be 20 ~ 40cm, and the weeds are growing in the peak period. 20% water agent 90~180mL/100 for control of annual weeds and 20% ~ 270mL/180 m2 water agent 100 for control of perennial weeds, diluted with water 6kg and sprayed on weed stems and leaves and soil surface. It is reported that the control effect can be improved by adding 3 to 4.5G of a wetting agent such as neutral detergent powder to the stem and leaf treatment. It can be mixed with atrazine in sugarcane field with high density of broad-leaved weeds. |
| production method | preparation method-preparation of methyl 4-acetylaminobenzenesulfonylcarbamate first, P-aminobenzenesulfonamide is reacted with acetyl chloride, P-acetamidobenzenesulfonamide was formed and the amino group was protected. A mixture of 2.14kg (10.0mol) 4-acetylaminobenzenesulfonamide, 12.7g (1.14kg mol) of anhydrous potassium carbonate and 16L of acetone is then slowly added with stirring 12.1 (mol) of methyl chloroformate. After addition, the mixture was heated at reflux for 18h, cooled to room temperature, and filtered. The filter cake was suspended in water and acidified to acid with hydrochloric acid to give a crude product. The crude product was dissolved in sodium bicarbonate solution, filtered, and the filtrate was acidified with hydrochloric acid to give 1.25 (45.9%) of a refined product, m. P. 235-237 °c. Synthesis of sulfasalazine G (2.1mol) of methyl 4-acetylaminobenzenesulfonylcarbamate was dissolved in 2mol/L sodium hydroxide solution, which was placed at room temperature for 2 days and then acidified to acid with concentrated hydrochloric acid to filter out the precipitate, extraction was carried out with 2mol/L hydrochloric acid, the extracted hydrochloric acid was added to the above filtrate, and then the pH value was adjusted to 4 with 50% sodium hydroxide to give sulfadiazine 289G (1.25mol) in 60% yield. P. 145-146 °c. Hydrochloric acid extraction insoluble (218g, 0.8mol) can be recycled. The yield of hydrolysis was 96%. The preparation method is Reflux reaction of methyl chloroformate and methanol to remove one molecule of hydrogen chloride to generate dimethyl carbonate; Then, dimethyl carbonate is reacted with sulfanilamide in the presence of sodium methoxide to generate sulfaniline. |
| category | pesticide |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 2000 mg/kg; Oral-mouse LD50: 5000 mg/kg |
| flammability hazard characteristics | toxic nitrogen oxide and sulfur oxide gases generated by combustion |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored and transported separately from food raw materials |
| extinguishing agent | dry powder, foam, sand |
| 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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CAS: 3337-71-1
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Raw Materials for [(4-Aminophenyl)sulfonyl]carbamic acid methyl ester