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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 439
実験および物理化学的性質
Pesticides
Pesticide -> EPA IRIS
Insecticides, Nematicides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Carbamate Insecticides
Insecticides, Nematicides
Environmental transformation -> Pesticides (parent, predecessor)
Physical Description
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
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
- 貯蔵温度
- 0 · 0-6°C
- 溶解性
- Chloroform (Slightly), Methanol (Slightly)
- 外見
- Liquid
- 水溶解度
- 0.3 mg · 0.3 mg l-1 (25 °C)
- 酸解離定数(Pka)
- 3.15 · 3.15±0.70(Predicted)
- 色
- Light brown to brown
- Merck
- 13 · 13,1836
- Henry's Law Constant
- 1.9 · 1.9×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- 主な用途
- 農業環境
- 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
- 6.05 · 6.050 (est)
- CAS データベース
- 55285 · 55285-14-8(CAS DataBase Reference)
- NISTの化学物質情報
- 2 · Carbamic acid, [(dibutylamino)thio]methyl-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester(55285-14-8)
- EPAの化学物質情報
- Carbosulfan (55285-14-8)
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
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
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.)
Hazards Summary
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.
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.
Hazard Classes and Categories
Acute Tox. 3 (100%)
Acute toxicity - category 2
Acute toxicity (Oral) - Category 3
Acute Tox. 2 *
安全と保護具
Exposure Control and Personal Protection
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]
毒性情報
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.
Health Effects
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).
Toxicity Summary
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
Carbosulfan
1 x 10 ^-2 mg/kg-day
RAIS Toxicity Values
0.01
IRIS Current
Hazard Quotient Level 0.1 or Cancer Risk Level 1E-06
6.30e+02
8.20e+03
5.10e+01
5.00e+00
1.20e+00
1.00e-02
Hazard Quotient Level 3 or Cancer Risk Level 1E-04
1.90e+03
2.50e+04
1.50e+02
5.00e+00
1.00e-02
Volatile
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
- 消防法
- 危-4-3-III
- hazard_code
- T;N,N,T,T+
- safety_code
- 24-37-38-45-60-61-63-36/37-28
- hazard_class
- 6.1(b)
- packing_group
- III
- 毒劇物取締法
- III
- Hazard Classifications
- Acute Tox. 1 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Skin Sens. 1
- ストレージクラス
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
化学と産業
薬理情報
Metabolism/Metabolites
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
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
Environmental transformation -> Pesticides (parent, predecessor)
Insecticides, Nematicides
応用分野
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.
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