DIMETHENAMID-P

Dimethanamid-P is a soil-applied herbicide. It is highly soluble in water and has a low volatility. It is not expected to be persistent in soil systems but may be persistent in water depending on local conditions. It is moderately toxic to birds, fish, aquatic invertebrates and algae but more so to aquatic plants. It is also moderately toxic to earthworms whilst its honeybee toxicity is low. Dimethenamid-P is also moderately toxic to mammals if ingested and is a skin and eye irritant, and a skin sensitizer.

Herbicide.

ChEBI: The (S)-enantiomer of 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-[(2S)-1-methoxypropan-2-yl]acetamide. It is the active enantiomer of dimethenamid, a herbicide applied to the soil to con rol various broad-leaved weeds and grasses.

The commercial production of dimethenamid-P involves a stereoselective multi-step synthesis to ensure high enantiomeric purity for enhanced efficacy and reduced environmental impact. It begins with the acid-catalysed condensation of 2,4-dimethyl-3-thiophenamine with (2S)-1-methoxypropan-2-amine to form the secondary amine intermediate, followed by etherification using a methylating agent like dimethyl sulphate in the presence of a base to yield the N-substituted amine. This intermediate then undergoes acylation with chloroacetyl chloride under basic conditions to produce the active substance.

Selective. Inhibition of very long chain fatty acids (VLCFA, inhibition of cell division)

Herbicide