HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Carbosulfan
DBSC · Versal · marshall · BRIGHT · Advantage · 2,3-Dihydro-2,2-dimethyl-7-benzofuran-N-(2-n-butylaminothio)-N-methylcarbamate · Posse · AMITAGE
Identifikatoren & physikalische Daten
| CAS No. | 55285-14-8 |
|---|---|
| Summenformel | C20H32N2O3S |
| Durchschnittliche Molmasse | 380,5 g/mol |
| Monoisotopische Masse | 380,21336388 g/mol |
| SMILES | CCCCN(CCCC)SN(C)C(=O)Oc1cccc2c1OC(C)(C)C2 |
| InChIKey | JLQUFIHWVLZVTJ-UHFFFAOYSA-N |
| PubChem CID | 41384 |
| ChEMBL | CHEMBL2228572 |
| ChEBI | CHEBI:38476 |
| EC No. | 259-565-9 |
| DTXSID | DTXSID5023950 |
| Lokaler Name | Carbosulfan |
Chemische & physikalische Eigenschaften
| XLogP | 5,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 67,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 10 |
| Schwere Atome | 26 |
| Formalladung | 0 |
| Komplexität | 439 |
| Pestizide | Pesticide -> EPA IRISInsecticides, NematicidesActive substance -> EU Pesticides database: Not approvedPesticides -> Carbamate InsecticidesEnvironmental transformation -> Pesticides (parent, predecessor) |
| LogP (Verteilungskoeffizient) | 5.0 |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Dampfdruck | 0.00000031 [mmHg]3.1 x 10-5 Pa (20 °C) |
| Physical Description | Carbosulfan is a viscous brown liquid.Brown viscous liquid[Merck Index] Medium yellow viscous liquidOdorless to slight amine odor[EFSA: DAR - Vol. 1] |
| Collision Cross Section | 188.3 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID5023950]190.66 Ų [M+H]+ [CCS Type: TWIonization: GC-APCI+] |
| Schmelzpunkt | <25 °C |
| Siedepunkt | approximate 126℃ |
| Dichte | 1.0560 |
| Brechungsindex | 1.6360 (estimate) |
| Flammpunkt | 96 °C |
| Lagerbedingungen | 0-6°C |
| Löslichkeit | Chloroform (Slightly), Methanol (Slightly)0.3 mg l-1 (25 °C) |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 3.15±0.70(Predicted) |
| Farbe | Light brown to brown |
| Merck | 13,1836 |
| Henry-Konstante | 1.9×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Hauptanwendungen | agricultureenvironmental |
| InChI | 1S/C20H32N2O3S/c1-6-8-13-22(14-9-7-2)26-21(5)19(23)24-17-12-10-11-16-15-20(3,4)25-18(16)17/h10-12H,6-9,13-15H2,1-5H3 |
| InChIKey | JLQUFIHWVLZVTJ-UHFFFAOYSA-N |
| SMILES | CCCCN(CCCC)SN(C)C(=O)Oc1cccc2CC(C)(C)Oc12 |
| LogP (Verteilungskoeffizient) | 6.050 (est) |
| CAS Datenbank | 55285-14-8(CAS DataBase Reference) |
| NIST chemische Informationen | Carbamic acid, [(dibutylamino)thio]methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester(55285-14-8) |
| EPA chemische Informationen | Carbosulfan (55285-14-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P333+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Commission Regulation (EC) No 451/20002007/415The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Gesundheitsgefahren | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Gefahrenübersicht | Carbamate cholinesterase inhibitorHydrolyzed to carbofuran in the soil[Merck Index] Insecticidal activity from the in vitro cleavage of the N-S bond forming carbofuranNot irritating to skin or eyesMay cause skin sensitizationDevelopmental toxicity and teratogenicity observed in rats and rabbits at doses not overtly maternally toxicNo evidence of carcinogenicity or organophosphorus induced delayed neurotoxicity [EFSA: DAR - Vol. 1] A mild skin irritant[RTECS] A mild skin irritantToxic by ingestion and inhalation[Sigma-Aldrich MSDS] See Carbofuran. See CARBAMATE INSECTICIDES. |
| Reaktive Gruppe | Thiocarbamate Esters and Salts/Dithiocarbamate Esters and Salts |
| Reactivity Profile | CARBOSULFAN is a thiocarbamate. Flammable gases are generated by the combination of thiocarbamates and dithiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates and dithiocarbamates are incompatible with acids, peroxides, and acid halides. |
| Air and Water Reactions | Thio and dithiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids. |
| Hazard Classes and Categories | Acute Tox. 3 (100%)Acute toxicity - category 2Acute toxicity (Oral) - Category 3Acute Tox. 2 * |
| Brandbekämpfung | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Erste Hilfe | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| 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] |
| Freisetung ohne Brand | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| 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). |
| Unerwünschte Wirkungen | Other Poison - Carbamate |
| Expositionspfade | Inhalation (L793)oral (L793)dermal (L793) |
| Toxizitätsübersicht | Carbosulfan 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) |
| EPA IRIS Information | Carbosulfan1 x 10 ^-2 mg/kg-day |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Toxicity Data | LC50 (rat) = 1,530 mg/m3/1hr |
| RAIS Toxicity Values | 0.01IRIS Current |
| Hazard Quotient Level 0.1 or Cancer Risk Level 1E-06 | 6.30e+028.20e+035.10e+015.00e+001.20e+001.00e-02 |
| Hazard Quotient Level 3 or Cancer Risk Level 1E-04 | 1.90e+032.50e+041.50e+025.00e+001.00e-02Volatile |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 2810 |
| RTECS-Nr. | EZ3815000 |
| R-Sätze (R) | 23/25-43-50/53-26-25 |
| Toxizität | LD50 in male, female rats (mg/kg): 250, 185 orallyin male, female rabbits (mg/kg): >2000, >2000 dermallyin pheasant, mallard, quail (ppm): 26.2, 8.1, 81.6 orally. LC50 (96 hr) in bluegill, trout (ppb): 14.9, 42.4 (Maitlen). |
| Gefahrensymbole | TN,N,T,T+ |
| Sicherheitshinweise (S) | 24-37-38-45-60-61-63-36/37-28 |
| Gefahrenklasse | 6.1(b)Acute Tox. 1 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Skin Sens. 1 |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
Anwendungen & Verwendung
Beschreibung
Carbosulfan (8)，2,3-dihydro-2,2-dimethylbenzofuran- 7-yl(dibutylaminothio)methylcarbamate(IUPAC), is an orange to brown, clear viscous liquid (bp 124–128 C), miscible with organic solvents and solubility 0.3 ppm in water(25 C). It is closely related structurally to carbofuran,and like carbofuran, it is a cholinesterase inhibitor with systemic activity.
Verwenden
Carbosulfan is an insecticide with contact and stomach action. It is used to control a wide range of soil-dwelling and foliar pests in cotton, sugar beet, potato, rice, fruit, maize, vegetables, sugar cane and coffee.