Description
Acrinathrin is a synthetic pyrethroid that has a high insecticidal activity against a range of insects including mites. It has a low aqueous solubility, is semi-volatile and, based on its chemical properties, should not leach. Laboratory studies suggest it is moderately persistent in soils but will rapid degrade in aqueous systems. It has a low toxicity to humans but there is some concern that it may bio-accumulate. Acrinathrin is highly toxic to bees and most aquatic species, moderately toxic to birds and earthworms.
Chemical Properties
The pure product is white, odorless crystals. MPa 81.5°C, vapor pressure 390×10-9 Pa (25°C), [α] 20D + 17.5°C. Solubility at 25°C: Freely soluble in acetone, chloroform, dichloromethane, ethyl acetate, and dimethylformamide (solubility > 500 g/L), diisopropyl ether 170 g/L, ethanol 40 g/L, hexane 10 g/L, and water ≤ 0.02 mg/L. Partition sensitivity 180,000. Stable in acidic media, hydrolysis and epimerization occur at pH > 7. The original drug is stable for one week under 100 W light and is readily adsorbed and immobilized by soil.
Definition
ChEBI: Acrinathrin is a cyclopropanecarboxylate ester and an organofluorine compound. It has a role as a pyrethroid ester insecticide and a pyrethroid ester acaricide. It is functionally related to a diphenyl ether.
Production Methods
Acrinathrin is manufactured through a complex multi-step chemical synthesis designed to produce a single, highly active isomer of this pyrethroid insecticide. The process begins with the preparation of key building blocks such as cyano(3-phenoxyphenyl)methanol and a substituted cyclopropane carboxylic acid derivative containing trifluoromethyl groups. These components are then esterified under controlled conditions to form the acrinathrin molecule, which features three chiral centres and a double bond, resulting in 15 possible isomers, though only one is used commercially due to its superior insecticidal activity.
Mechanism of action
Contact and stomach action. Neurotoxin. Sodium channel modulator.
Pesticide Type
Insecticide; Acaricide
