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メチルカルバミド酸2-イソプロピルフェニル
メチルカルバミン酸2-イソプロピルフェニル · メチルカルバミド酸o-イソプロピルフェニル · エトロホラン · MIPC剤 · エトレホラン · ミプシン · イソプロカルブ · メチルカルバミド酸2-イソプロピルフェニル
識別子と物理属性
| CAS No. | 2631-40-5 |
|---|---|
| 分子式 | C11H15NO2 |
| 平均分子量 | 193.24 g/mol |
| 単同位体質量 | 193.11027872 g/mol |
| SMILES | CNC(=O)Oc1ccccc1C(C)C |
| InChIKey | QBSJMKIUCUGGNG-UHFFFAOYSA-N |
| PubChem CID | 17517 |
| ChEMBL | CHEMBL2251586 |
| ChEBI | CHEBI:38505 |
| EC No. | 220-114-6 |
| DTXSID | DTXSID6042072 |
| 現地名 | メチルカルバミド酸2-イソプロピルフェニル |
化学・物理的性質
| XLogP | 2.3 |
|---|---|
| 極性表面積 | 38.3 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 3 |
| 重原子数 | 14 |
| 形式電荷 | 0 |
| 複雑度 | 192 |
| SpringerMaterials Properties | Fusion temperature |
| 農薬 | Agrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: Not approvedPesticide (Isoprocarb) -> USDA PDB |
| LogP（分配係数） | 2.31 |
| 溶解度 | 0.4 mg/mL at 25 °CChloroform (Slightly), Methanol (Slightly) |
| 融点 | 88 - 93 °C92.4°C |
| Physical Description | Solid |
| 沸点 | 329.46°C (rough estimate) |
| 密度 | 1.0945 (rough estimate) |
| 屈折率 | 1.5080 (estimate) |
| 引火点 | -18 °C |
| 貯蔵条件 | Sealed in dry,2-8°C |
| 外観・状態 | 結晶性 |
| pKa（酸解離定数） | 12.22±0.46(Predicted) |
| 色 | White to off-white |
| BRN | 1875020 |
| ヘンリー定数 | 7.4×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 主な用途 | 農業環境 |
| InChI | InChI=1S/C11H15NO2/c1-8(2)9-6-4-5-7-10(9)14-11(13)12-3/h4-8H,1-3H3,(H,12,13) |
| InChIKey | QBSJMKIUCUGGNG-UHFFFAOYSA-N |
| SMILES | C1(OC(=O)NC)=CC=CC=C1C(C)C |
| CAS データベース | 2631-40-5(CAS DataBase Reference) |
| NISTの化学物質情報 | 2-(1-Methylethyl)phenyl methylcarbamate(2631-40-5) |
| EPAの化学物質情報 | Isoprocarb (2631-40-5) |
化学的特性
Isoprocarb is a carbamate insecticide. It is a colourless crystalline substance, sparingly soluble in water (0.265g/l) and readily soluble in acetone(400g/l) and methanol (125g/l). It is hydrolysed in alkaline media.The insecticide,with contact and stomach action, effectively controls leafhoppers,plant hoppers and aphids on a variety of crops like rice, cocoa, sugarcane and vegetables. Its residual activity gives effective pest control. It acts by inhibiting cholinesterase.
安全性と法規制
| GHS 分類 | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| DOT Hazard Classification | IsoprocarbMarine pollutant |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Acute toxicity - category 4Acute toxicity (Oral) - Category 3Acute Tox. 4 * |
| 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. |
| 健康影響 | 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). |
| 暴露経路 | Inhalation (L793)oral (L793)dermal (L793) |
| 毒性の概要 | 2-Isopropylphenyl 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) |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | FB7880000 |
| 輸送番号（UN） | UN 3077 9/PG 3 |
| PRTR法 | 第1種指定化学物質 |
| 税関コード | 29224999 |
| 危険文句（R） | 22-50/53-67-65-38-11-20 |
| 化審法 | 一般化学物質 |
| 危険表示 | Xn,N,F |
| 安全措置（S） | 60-61-62-33-16-9-25 |
| 毒劇物取締法 | III |
| 危険等級 | Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
説明
Isoprocarb, o-cumenyl methylcarbamate (IUPAC), consists of colorless crystals, which are sparingly soluble in water and are readily soluble in acetone and methanol. Isoprocarb is produced by reaction of 2-isopropylphenol with methylisocyanate. Isoprocarb is used for control of rice, cacao, sugarcane, and vegetable pests.
使用
Isoprocarb is a non-systematic carbamate insecticide. Isoprocarb functions by reversibly inactivating the enzyme acetylcholinesterase in insects.