Carbosulfan

HCID 41384CAS 55285-14-8

Grundinformationen

Standard-SMILES
CCCCN(CCCC)SN(C)C(=O)Oc1cccc2c1OC(C)(C)C2
InChIKey
JLQUFIHWVLZVTJ-UHFFFAOYSA-N
Summenformel
C20H32N2O3S
Durchschnittliche Molmasse
380,5 g/mol
Monoisotopische Masse
380,21336388

Überblick

Carbosulfan is a viscous brown liquid.

Namen und Bezeichner

Bevorzugter Name
Carbosulfan
IUPAC
(2,2-dimethyl-3H-1-benzofuran-7-yl) N-(dibutylamino)sulfanyl-N-methylcarbamate
Lokaler Name
Carbosulfan
Englischer Name
Carbosulfan
Summenformel
C20H32N2O3S
Molmasse
380.54

Namen und Synonyme

Carbosulfan55285-14-8MarshalPosseAdvantageMarshallCaswell No. 463CDibutylaminosulfenylcarbofuranFMC 35001DTXSID5023950V1DGN4AK6G2,3-Dihydro-2,2-dimethyl-7-benzofuranyl (di-n-butylaminosulfenyl)methylcarbamate
Weitere Namen anzeigen
DBSCVersalBRIGHT2,3-Dihydro-2,2-dimethyl-7-benzofuran-N-(2-n-butylaminothio)-N-methylcarbamateAMITAGESheriff
DTXCID603950CHEBI:38476Carbamic acid, ((dibutylamino)thio)methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester((Dibutylamino)thio)methylcarbamic acid 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl [(dibutylamino)sulfanyl](methyl)carbamateCarbamic acid, [(dibutylamino)thio]methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl ((dibutylamino)sulfanyl)(methyl)carbamateMarshal 10G

Datenbank-Bezeichner

CAS
55285-14-8
PubChem CID
41384
DTXSID
DTXSID5023950
ChEMBL
CHEMBL2228572
ChEBI
CHEBI:38476
UNII
V1DGN4AK6G
EC Number
259-565-9
Nikkaji
J1.070G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,7
Polarare Oberfläche (TPSA)
67,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
10
Schwere Atome
26

Experimentelle und physikochemische Eigenschaften

Pesticides · 6 Einträge

Pesticide -> EPA IRIS

Insecticides, Nematicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Carbamate Insecticides

Insecticides, Nematicides

Environmental transformation -> Pesticides (parent, predecessor)

LogP5.0
Endocrine DisruptorsPotential endocrine disrupting compound
Vapor Pressure0.00000031 [mmHg]
Physical Description · 2 Einträge

Carbosulfan is a viscous brown liquid.

Brown viscous liquid; [Merck Index] Medium yellow viscous liquid; Odorless to slight amine odor; [EFSA: DAR - Vol. 1]

Collision Cross Section · 2 Einträge

188.3 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID5023950]

190.66 Ų [M+H]+ [CCS Type: TW; Buffer gas: N2; Ionization: GC-APCI+]

Physikochemische Eigenschaften

Schmelzpunkt
25 °C · <25 °C
Siedepunkt
126 ℃ · approximate 126℃
Dichte
1.056 · 1.0560
Dampfdruck
3.1 x · 3.1 x 10-5 Pa (20 °C)
Brechungsindex
1.636 · 1.6360 (estimate)
Flammpunkt
96 °C · 96 °C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H301: 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)

Danger

H301 (100%): 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)

Gefahrenhinweise

Regulatory Information · 3 Einträge

Commission Regulation (EC) No 451/2000

2007/415

The 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 LabelPoison
Fire HazardsExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Health HazardsExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Hazards Summary · 1 Eintrag

Carbamate cholinesterase inhibitor; Hydrolyzed to carbofuran in the soil; [Merck Index] Insecticidal activity from the in vitro cleavage of the N-S bond forming carbofuran; Not irritating to skin or eyes; May cause skin sensitization; Developmental toxicity and teratogenicity observed in rats and rabbits at doses not overtly maternally toxic; No evidence of carcinogenicity or organophosphorus induced delayed neurotoxicity [EFSA: DAR - Vol. 1] A mild skin irritant; [RTECS] A mild skin irritant; May cause skin sensitization; Toxic by ingestion and inhalation; [Sigma-Aldrich MSDS] See Carbofuran. See CARBAMATE INSECTICIDES.

Reactive GroupThiocarbamate Esters and Salts/Dithiocarbamate Esters and Salts

Sicherheit und Schutzausrüstung

Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
First AidExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Exposure Control and Personal Protection · 1 Eintrag

Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]

Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Isolation and EvacuationExcerpt 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)]:

Toxikologische Informationen

Treatment · 1 Eintrag

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.

Health Effects · 1 Eintrag

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).

Adverse EffectsOther Poison - Carbamate
Exposure RoutesInhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 Eintrag

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 · 1 Eintrag

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)

Sicherheitsdaten

wgk
3
ridadr
UN 2810
RTECS-Nr.
EZ3815000
risk_code
23/25-43-50/53-26-25
Toxizität
LD50 in male, female rats (mg/kg): 250, 185 orally; in male, female rabbits (mg/kg): >2000, >2000 dermally; in pheasant, mallard, quail (ppm): 26.2, 8.1, 81.6 orally. LC50 (96 hr) in bluegill, trout (ppb): 14.9, 42.4 (Maitlen).
hazard_code
T;N,N,T,T+

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

Carbosulfan has known human metabolites that include (2,2-dimethyl-3H-1-benzofuran-7-yl) N-dibutylsulfinamoyl-N-methylcarbamate, dibutyl(sulfanyl)amine, and Carbofuran.

The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

Verwendung und Herstellung

Uses · 3 Einträge

No active pesticide product registrations in the US; [NPIRS] Used as an insecticide; [Merck Index] Approved in the EU for use on maize, sugarbeet, cotton, and citrus; [EFSA: DAR - Vol. 1]

Farming (Pesticides) [Category: Industry]

Carbosulfan is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

Use Classification · 2 Einträge

Environmental transformation -> Pesticides (parent, predecessor)

Insecticides, Nematicides

Anwendungen · 2 Einträge

BeschreibungCarbosulfan (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.

VerwendenCarbosulfan 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.

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