Isoprocarb

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

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.

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.

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.

Pesticide Type

Insecticide