Description
Chlorquinox is an obsolete fungicide that was used to control powdery mildew. The chemical has not been extensively studied and there is little available information. The substance is moderately toxic to birds and has a low mammalian toxicity.
Definition
ChEBI: A quinoxaline antifungal agent that is quinoxaline in which the hydrogens at positions 5, 6, 7, and 8 are replaced by chlorines. Chlorquinox was developed in the 1970s and was used on crops for the control of powdery mildew; it is now obsolete.
Production Methods
Chlorquinox production would begin with a 1,2 phenylenediamine derivative, which is condensed with a tetrachloro substituted 1,2 dicarbonyl compound to form the quinoxaline heterocycle. This cyclocondensation reaction, typical for quinoxaline synthesis, proceeds under acidic or thermal conditions, after which the crude compound is purified by solvent extraction and recrystallisation to yield technical grade chlorquinox.
Mechanism of action
Multi-site contact activity. Disrupts fungal respiration, targeting complex II of the mitochondrial electron transport chain preventing the fungus from generating energy
