Description
Butroxydim is an obsolete herbicide. It has a low aqueous solubility, is relatively volatile and, based on its chemical properties, is non-mobile and would not be expected to leach to groundwater. It is generally non-persistent in soil systems but may persist in aquatic systems under certain conditions. It is not generally susceptible to hydrolysis. It has a moderate mammalian toxicity and has a high potential to bioaccumulate. It is moderately toxic to most aquatic species, birds and earthworms but relatively non-toxic to honeybees.
Production Methods
The production of butroxydim involves synthesising a cyclohexane-1,3-dione core, which serves as the backbone for its herbicidal activity. The process begins with constructing the substituted aromatic ring, typically a 3-butanoyl-2,4,6-trimethylphenyl group, through Friedel–Crafts acylation and methylation reactions. This aromatic moiety is then coupled to the cyclohexanedione ring via condensation, forming a stable enone intermediate. Next, the key oxime ether side chain is introduced by reacting the enone with ethoxyamine, yielding the biologically active ketoxime structure.
Definition
ChEBI: Butroxydim is a butanone.
Mechanism of action
Selective and systemic. Absorbed by leaves and translocated. Acetyl CoA carboxylase inhibitor (ACCase) - distrupts fatty acid biosynthesis and lipid formation.
