Amiprofos methyl

Amiprofos-methyl (APM) is a phosphoric amide herbicide. It reversibly decreases H. vulgare root and shoot length and inhibits in vitro polymerization of Rosa tubulin induced by paclitaxel in a dose-dependent manner. APM completely inhibits tubulin polymerization in Hemanthus endosperm cells at a concentration of 0.1 μM. The antitubulin effects of APM are specific to plants as it has no effect on bovine brain tubulin polymerization at concentrations up to 100 μM. APM inhibits calcium accumulation in corn mitochondria (ID₅₀ = 140 nM) and induces a 3-fold increase in the rate of calcium efflux from rat liver mitochondria at a concentration of 100 nM. APM inhibits the growth of P. falciparum (IC₅₀ = 3.5 μM) and completely inhibits microtubule polymerization in P. falciparum trophozoites at a concentration of 20 μM.

It is white or light yellow crystal with slight odor. m.p. 64～65℃. It is soluble in organic solvents such as benzene, alcohol, ester, etc. The solubility is 10mg/L in water.

Amiprofos-methyl is useful in herbicide compositions.

Amiprofos-methyl is commercially produced involves the synthesis of O-methyl O-(4-methyl-2-nitrophenyl) N-isopropylphosphoramidothioate, typically through esterification and amidation reactions involving nitrophenol derivatives and isopropylamine with a phosphorothioate intermediate.

Herbicide that prevents microtubule polymerization in plant cells, but not animal cells. Crop plants resistant to amiprofos-methyl and several other herbicides have been developed by insertion of a xenobiotic-detoxifying human gene CYP2B6.

Inhibits the post mitotic migration of the nucleus and the chloroplast in Micrasterias denticulata Bréb. Microtubule assembly inhibition.

A poison by ingestion. Lowtoxicity by skin contact. When heated to decomposition itemits toxic vapors of NOx, SOx, and POx.

[1] LOUIS C. MOREJOHN  Donald E F. Inhibition of Plant Microtubule Polymerization in vitro by the Phosphoric Amide Herbicide Amiprophos-Methyl[J]. Science, 1984, 224 4651. DOI: 10.1126/science.224.4651.874
[2] A. TEMEL N G. Cytotoxic effects of metaphase-arresting methods in barley[J]. Cytology and Genetics, 2015, 49 1: 382-387. DOI: 10.3103/s0095452715060109
[3] CORNELIA HERTEL . Herbicides and fungicides stimulate Ca2+ efflux from rat liver mitochondria[J]. FEBS Letters, 1981, 127 1: Pages 37-39. DOI: 10.1016/0014-5793(81)80335-3
[4] BRIAN J. FENNELL. Cellular and molecular actions of dinitroaniline and phosphorothioamidate herbicides on Plasmodium falciparum: Tubulin as a specific antimalarial target[J]. Molecular and biochemical parasitology, 2006, 145 2: Pages 226-238. DOI: 10.1016/j.molbiopara.2005.08.020

Herbicide