Chlorthion

Description

Chlorthion is an organophosphate insecticide. It has a moderate aqueous solubility and not considered to be volatile. Chlorthion is not persistent in soil systems and, based on its physico-chemical properties, it is only slightly mobile and not expected to leach to groundwater. It is moderately toxic to most biodiversity but there may be a higher risk for bees. It has a moderate mammalian toxicity, is a cholinesterase inhibitor and a neurotoxin.

Uses

Insecticide.

Definition

ChEBI: Chlorthion is an organic thiophosphate that is O,O-dimethyl O-phenyl phosphorothioate substituted by a chloro group at position 3 and a nitro group at position 4. It is a potent cholinesterase inhibitor and used as an insecticide for the control of a wide range of insects. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor and an agrochemical. It is a C-nitro compound, an organic thiophosphate, a member of monochlorobenzenes and an organothiophosphate insecticide.

Production Methods

Chlorthion is commercially synthesised through the esterification of dimethyl phosphorothioic acid with 3-chloro-4-nitrophenol under controlled conditions. This process involves reacting O,O-dimethyl phosphorothioic acid chloride with 3-chloro-4-nitrophenol in the presence of a base such as pyridine or triethylamine, typically in an organic solvent like toluene or dichloromethane. The reaction is conducted at moderate temperatures to ensure selectivity and minimise byproducts.

Mechanism of action

Broad-spectrum with contact, stomach and respiratory action. Acetylcholinesterase (AchE) inhibitor.

Pesticide Type

Insecticide; Larvicide