| Identification | More | [Name]
Isoprocarb | [CAS]
2631-40-5 | [Synonyms]
2-(1-METHYLETHYL)PHENYL METHYL-CARBAMATE
Entrofolan
ETROFOLAN
ETROFOLAN(R)
Hytox
ISOPROCARB
Isoprocarb emulsion
MIPC
MIPC emulsion
Mipcide
Mipcide emulsion
MIPCIN
Mipcin emulsion
MIPCIN(R)
O-CUMENYL METHYL CARBAMATE
2-(1-Methylethyl)-phenol methyl-carbamate
2-(1-methylethyl)-phenomethylcarbamate
2-(1-Methylethyl)phenylmetylcarbamate
2-Isopropylphenyl methylcarbamate
2-Isopropylphenyl N-methylcarbamate | [EINECS(EC#)]
220-114-6 | [Molecular Formula]
C11H15NO2 | [MDL Number]
MFCD00053078 | [Molecular Weight]
193.24 | [MOL File]
2631-40-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
92.4°C | [Boiling point ]
329.46°C (rough estimate) | [density ]
1.0945 (rough estimate) | [refractive index ]
1.5080 (estimate) | [Fp ]
-18 °C | [storage temp. ]
0-6°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Crystalline | [pka]
12.22±0.46(Predicted) | [color ]
White to off-white | [BRN ]
1875020 | [Henry's Law Constant]
7.4×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) | [Major Application]
agriculture
environmental | [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 DataBase Reference]
2631-40-5(CAS DataBase Reference) | [NIST Chemistry Reference]
2-(1-Methylethyl)phenyl methylcarbamate(2631-40-5) | [EPA Substance Registry System]
2631-40-5(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS07,GHS09 | [Signal word ]
Warning | [Hazard statements ]
H302-H410 | [Precautionary statements ]
P273-P301+P312+P330 | [Hazard Codes ]
Xn,N,F | [Risk Statements ]
R22:Harmful if swallowed.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R67:Vapors may cause drowsiness and dizziness.
R65:Harmful: May cause lung damage if swallowed.
R38:Irritating to the skin.
R11:Highly Flammable. | [Safety Statements ]
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S33:Take precautionary measures against static discharges .
S16:Keep away from sources of ignition-No smoking .
S9:Keep container in a well-ventilated place . | [RIDADR ]
UN 3077 9/PG 3 | [WGK Germany ]
3 | [RTECS ]
FB7880000 | [TSCA ]
TSCA listed | [HS Code ]
29224999 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1 | [Safety Profile]
Poison by ingestion,
intravenous, and intraperitoneal routes.
Moderately toxic by skin contact. When
heated to decomposition it emits toxic
fumes of NOx. See also CARBAMATES.
Used for controlling leafhoppers,
planthoppers, and bugs in rice and cacao. |
| Hazard Information | Back Directory | [Description]
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. | [Chemical Properties]
White Solid | [Uses]
Isoprocarb is a non-systematic carbamate insecticide. Isoprocarb functions by reversibly inactivating the enzyme acetylcholinesterase in insects. | [Definition]
ChEBI: Isoprocarb is a carbamate ester. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a carbamate insecticide and an agrochemical. It is functionally related to a methylcarbamic acid and a 2-isopropylphenol. | [Production Methods]
Isoprocarb is commercially produced via a concise 2–3 step synthesis that begins with the preparation of 2-isopropylphenyl chloroformate by reacting 2-isopropylphenol with phosgene in toluene in the presence of a catalytic amount of DMF. The key carbamoylation occurs through nucleophilic addition of methylamine to the chloroformate intermediate under controlled pH to form the methylcarbamate linkage, minimizing hydrolysis. Final purification via vacuum distillation or crystallisation from hexane yields isoprocarb. | [Mechanism of action]
Contact and stomach action. Acetylcholinesterase (AChE) inhibitor. | [Toxicology]
The insecticide isoprocarb is a Class II toxin (moderately hazardous), with the acute oral LD50 among rats being 403-485mg/kg, while the percutaneous LD50 among male rats and mice is>500mg. It is a PAN Bad Actor chemical, since it is a cholinesterase inhibitor. Symptoms of poisoning with this insecticide include muscle weakness,dizziness,salivation,nausea,vomiting,sweating,headache,effects on the CNS and depression. PPE such as splash-resistant safety goggles and chemicalresistant clothing, gloves and masks are advised. | [Pesticide Type]
Insecticide |
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