isofetamid

Uses

Isopropylthiamethoxam can be used as a novel amide-based bactericide.

Definition

ChEBI: Isofetamid is an aromatic amide obtained by formal condensation of the carboxy group of 3-methylthiophene-2-carboxylic acid with the amino group of 2-amino-1-(4-isopropoxy-2-methylphenyl)-2-methylpropan-1-one. It has a role as an EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor and an antifungal agrochemical. It is an aromatic ether, an aromatic amide, a member of thiophenes, an aromatic ketone and an amide fungicide.

Production Methods

Isofetamid is produced industrially through a multistep synthetic route that builds its characteristic phenyl oxo ethyl amide structure, beginning with m cresol, which undergoes Friedel–Crafts acylation, etherification, alpha ketobromination, and azide substitution to generate the key phenethylamine intermediate. This amine is then coupled with 3 methylthiophene 2 carbonyl chloride to form the final amide bond, yielding isofetamid after purification. Recent patents describe optimised commercial processes that introduce novel protected intermediates and improved amidation conditions to enhance yield, purity, and process safety in large scale manufacturing. Overall, the industrial synthesis follows a classical aromatic amide assembly strategy but incorporates modern refinements to support efficient, high purity fungicide production.

Mechanism of action

Locally systemic, broad-spectrum. Succinate Dehydrogenase Inhibitor (SDHI)

Pesticide Type

Fungicide