Butamifos is an organophosphate herbicide used to control annual and graminaceous weeds. It has a low aqueous solubility but other environmental fate related data is scarce. Generally, butamifos is moderately toxic to biodiversity. It is also moderately toxic to mammals if ingested and is thought to be an acetyl cholinesterase inhibitor.
Butamifos (S-2846) is an organophosphoramidate herbicide used to control annual weeds with low toxicity to mammals. Butamifos acts on the growing points of susceptible plants, causing severe radial enlargement of the affected tissues[1].
ChEBI: Butamifos is a C-nitro compound.
The commercial production of butamifos involves the reaction of phosphorus-containing intermediates with nitrophenol derivatives and sec-butylamine, forming the active compound: O-ethyl O-(5-methyl-2-nitrophenyl) N-sec-butylphosphoramidothioate. The process includes esterification and amidation steps under controlled conditions to ensure the correct configuration and herbicidal activity
Microtubule assembly inhibition. Non-systemic, selective
In water, butamifos undergoes photoinduced
intramolecular oxygen transfer from the nitro group to
the P=S moiety, resulting in the formation of the
nitrosooxon derivative. Through the successive
reduction of the nitroso group to hydroxyamino and
amino groups, as well as oxidation to the nitro group,
the nitrosooxon derivative is finally photodegraded to
various polar compounds. The isomer of butamifos is
photodegraded more slowly than butamifos in air, and
its main photodegradation pathway in water is
oxidation of the arylmethyl group to form a
corresponding carboxylic acid derivative.
[1] SUMIDA S, et al. Chlorella as a model system to study herbicidal mode of action and its application to a new herbicide, O-ethyl-O-(3-methyl-6-nitrophenyl)-N-sec-butyl phosphorothioamidate (S-2846)[M]. 1974.
