Definition
ChEBI: Azafenidin is a triazolopyridine that is 5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one which is substituted at position 2 by a 2,4-dichloro-5-(prop-2-yn-1-yloxy)phenyl group. A protoporphyrinogen oxidase inhibitor, it is used as a herbicide to control weeds in fruit crops such as pineapple, citrus, melons, and grapes. Not approved for use within the European Union. It has a role as an EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor. It is a triazolopyridine, a terminal acetylenic compound and a dichlorobenzene.
Metabolic pathway
A common degradation reaction of azafenidin in light,
plants and soil is O-dealkylation, and interesting minor
reactions in soil are the subsequent methylation of the
O-dealkylated degradation product and the reduction
of the propynyl group under anaerobic conditions. In
soil and light, azafenidin is also readily split to form
the triazolinone heterocycle. Azafenidin is readily
metabolized in rats and lactating goats through
O-dealkylation, hydroxylation of the triazolinone ring
in several positions, and glucuronide and sulfate
conjugation.
