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M-(1-Ethylpropyl)phenyl methylcarbamate
3-(3-Pentanyl)phenyl methylcarbamate · 3-(1-Ethylpropyl)phenyl MethylcarbaMate · Phenol, 3-(1-ethylpropyl)-, 1-(N-methylcarbamate)
Identifikatoren & physikalische Daten
| CAS No. | 672-04-8 |
|---|---|
| Summenformel | C13H19NO2 |
| Durchschnittliche Molmasse | 221,29 g/mol |
| Monoisotopische Masse | 221,14157885 g/mol |
| SMILES | CCC(CC)c1cccc(OC(=O)NC)c1 |
| InChIKey | SMSFWBAOKCZZBF-UHFFFAOYSA-N |
| PubChem CID | 12643 |
| DTXSID | DTXSID1042102 |
Chemische & physikalische Eigenschaften
| XLogP | 3,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 38,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 16 |
| Formalladung | 0 |
| Komplexität | 214 |
| Pestizide | Pesticides -> Carbamate Insecticides |
| Stability/Shelf Life | It is stable in neutral or acid soln, but the rate of hydrolysis incr with rise in either pH or temp. /bufencarb/May decomp when exposed to sunlightmoderate to low volatility /bufencarb/ |
| Other Experimental Properties | Colorless, low melting solidMP: 40-45 °Cdensity: 1.031 at 25 °CBP: 125-130 °C at 0.1 mm Hgmoderate to low volatilitysolubility in water is less than 0.01%soluble in most solvents but less in aliphatic hydrocarbons /bufencarb/A low melting solid, yellow to amber in colorMP: 26-39 °Cvapor pressure: 3x10-5 mm Hg at 30 °CBP: about 125 °C at 0.04 mm Hgdensity: 1.024 at 26 °C /bufencarb, technical product/ |
| EPA chemische Informationen | m-(1-Ethylpropyl)phenyl methylcarbamate (672-04-8) |
Sicherheit & Vorschriften
| Gefahrenübersicht | A cholinesterase inhibitorToxic if ingested or absorbed through the skin[HSDB] See m-(1-Methylbutyl)phenyl methylcarbamate. See CARBAMATE INSECTICIDES. |
|---|---|
| Expositionsschutz und Persönliche Schutzausrüstung | Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baselineButylcholinesterase activity in serum or plasma = 60% of individual's baselineSample at end of shift[TLVs and BEIs] |
| Treatment | If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally. |
| Gesundheitliche Auswirkungen | Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing. (A15321) |
| Ökotoxizitätswerte | LC50 Japanese quail oral more than 5000 ppm in 5-day diet (8% mortality at 2236 ppm, 42% at 5000 ppm) /bux/LC50 Ring-necked pheasants oral more than 5000 ppm in 5-day diet (no mortality to 5000 ppm) /bux/LC50 Mallards oral more than 5000 ppm in 5-day diet (12% mortality at 1000 ppm, 38% at 5000 ppm) /bux/LD50 pheasants oral greater than 27000 mg/kg in 8-day dietFor more Ecotoxicity Values (Complete) data for M-(1-ETHYLPROPYL)PHENYL METHYLCARBAMATE (8 total), please visit the HSDB record page. |
| Umweltverhalten | Terrestrial Fate: It is degraded fairly rapidly in soil and no carry-over would be expected from one season to the next with granules. /bufencarb/ |
| Unerwünschte Wirkungen | Other Poison - Carbamate |
| Expositionspfade | Inhalation (L793)oral (L793)dermal (L793) |
| Toxizitätsübersicht | 3-(1-Ethylpropyl)phenyl methylcarbamate is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. |
| Signs and Symptoms | As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795) |
| Human Toxicity Excerpts | Symptomatology: 1. Nausea, vomiting, abdominal cramps, diarrhea & excessive salivation...sweating. 2. Lassitude & weakness. 3. Rhinorrhea and sensation of tightness in chest may occur with inhalation exposure. 4. Blurring or dimness of vision. Miosis...tearing, ciliary muscle spasm, loss of accommodation and ocular pain. None of these...signs...is dependable for diagnosis. Mydriasis may be seen... 5. Loss of muscle coordination, slurring of speech, fasciculation & twitching of muscles. 6. Difficulty in breathing, excessive secretions of saliva and of resp tract mucus, oronasal frothing, cyanosis, pulmonary rales & rhonchi, and hypertension. 7. ...jerky movements, incontinence, convulsions and coma. 8. Death...due to resp arrest of central origin, paralysis of resp muscles, intense bronchoconstriction or all three. /Carbaryl/Four spraymen and one mixer applied 6 to 7 pump charges of bufencarb during the first day and 9 to 10 pump charges during the second day... One sprayman complained of "hunger cramps" in his stomach...the same sprayman and another one reported that they had vomited... Cholinesterase activity was depressed to about 50% of normal... During the second day one sprayman vomited while at work... His pulse rate was 52 per min and he experienced some sweating, dizziness, and pupillary change. /bufencarb/ |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Non-Human Toxicity Excerpts | NITROSO DERIV OF THE TESTED METHYL CARBAMATE INSECTICIDES, INCL BUX-TEN, ARE POTENT MUTAGENS, BUT PARENT INSECTICIDES ARE NON-MUTAGENIC.Toxic if ingested or absorbed through the skin, it inhibits cholinesterase activity in red blood cells. /bufencarb/Very toxic to fish. Causes a variety of teratogenic effects in chick eggs when injected into the yolk sac. /bufencarb//Acute oral toxicity in birds/ Ataxia, dyspnea, wing-drop, tremors, regurgitation, ptosis, and wing-beat convulsions or tetany. Signs appeared as soon as 15 min and mortalities usually occurred between 20 min and 1 hr after treatment. /bufencarb/ |
| Environmental Abiotic Degradation | May decomp when exposed to sunlight. /bufencarb/ |
| Gefahrstoffdaten | 672-04-8(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
3-(1-Ethylpropyl)phenyl Methylcarbamate is a component of the carbamate insecticide Bufencarb (B689385).