N-(ジブチルアミノチオ)-N-メチルカルバミド酸2,3-ジヒドロ-2,2-ジメチルベンゾフラン-7-イル

Carbosulfan

HCID 41384CAS 55285-14-8

基本情報

標準SMILES
CCCCN(CCCC)SN(C)C(=O)Oc1cccc2c1OC(C)(C)C2
InChIKey
JLQUFIHWVLZVTJ-UHFFFAOYSA-N
分子式
C20H32N2O3S
平均分子量
380.5 g/mol
単同位体質量
380.21336388

概要

Carbosulfan is a viscous brown liquid.

名称と識別子

優先名称
Carbosulfan
IUPAC
(2,2-dimethyl-3H-1-benzofuran-7-yl) N-(dibutylamino)sulfanyl-N-methylcarbamate
現地名
N-(ジブチルアミノチオ)-N-メチルカルバミド酸2,3-ジヒドロ-2,2-ジメチルベンゾフラン-7-イル
英語名
Carbosulfan
分子式
C20H32N2O3S
分子量
380.54

名称と別名

Carbosulfan55285-14-8MarshalPosseAdvantageMarshallCaswell No. 463CDibutylaminosulfenylcarbofuranFMC 35001DTXSID5023950V1DGN4AK6G2,3-Dihydro-2,2-dimethyl-7-benzofuranyl (di-n-butylaminosulfenyl)methylcarbamate
名称をさらに表示
カルボスルファンアドバンテージガゼットN-(N,N-ジブチルアミノチオ)-N-メチルカルバミド酸2,3-ジヒドロ-2,2-ジメチルベンゾフラン-7-イルマーシャルN-(ジブチルアミノチオ)-N-メチルカルバミド酸2,3-ジヒドロ-2,2-ジメチルベンゾフラン-7-イルN-ジブチルアミノチオ-N-メチルカルバミン酸2,3-ジヒドロ-2,2-ジメチル-7-ベンゾ[b]フラニルポッセカルボスルファン標準品2, 3-ジヒドロ-2, 2-ジメチル-7-ベンゾ[b]フラニル-N-ジブチルアミノチオ-N-メチルカルバマートN-ジブチルアミノチオ-N-メチルカルバミン酸2,3-ジヒドロ-2,2-ジメチル-7-ベンゾ[b]フラニル (別名 カルボスルファン)CS_N-11409-250MG_カルボスルファンカルボスルファン STANDARDカルボスルファン Standard, 100 µg/mL in MeOH2,2-ジメチル-2,3-ジヒドロ-1-ベンゾフラン-7-イル N-[(ジブチルアミノ)スルファニル]-N-メチルカルバマートN-シフチルアミノチオ-N-メチルカルハミン酸2,3-シヒトロ- 2,2-ジメチル-7-ベンゾ[b ]フラニルカルボスルファ ン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

データベース識別子

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

物性

構造計算による物性

XLogP
5.7
極性表面積
67.3 Ų
水素結合供与体数
0
水素結合受容体数
5
回転可能結合数
10
重原子数
26

実験および物理化学的性質

Pesticides · 6 件

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 件

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 件

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+]

物理化学的性質

融点
25 °C · <25 °C
沸点
126 ℃ · approximate 126℃
比重(密度)
1.056 · 1.0560
蒸気圧
3.1 x · 3.1 x 10-5 Pa (20 °C)
屈折率
1.636 · 1.6360 (estimate)
闪点
96 °C · 96 °C

化学的性質

化学的特性Orange-yellow thick liquid.

安全と法規制

GHS分類

GHS Classification · 6 件

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)

危険有害性情報

Regulatory Information · 3 件

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 件

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

安全と保護具

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 件

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)]:

毒性情報

Treatment · 1 件

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 件

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 件

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 件

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)

安全データ

wgk
3
rtecs
EZ3815000
ridadr
UN 2810
毒性
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).
PRTR法
第1種指定化学物質
risk_code
23/25-43-50/53-26-25

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

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)

用途と製造

Uses · 3 件

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 件

Environmental transformation -> Pesticides (parent, predecessor)

Insecticides, Nematicides

応用分野 · 4 件

用途氨基甲酸酯类殺虫

説明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.

使用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.

一般的な説明Viscous brown liquid.

関連反応

1 件

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