Destruction of chemical warfare agents VX and soman by α‐nucleophiles as oxidizing agents

Abstract

Reactions of O‐ethyl S‐(2‐diisopropyl‐amino)ethyl methylphosphonothiolate, VX 1, were investigated with five oxidizing agents. In all the cases, the formation of the VX N‐oxide 7 was observed prior to the subsequent oxidation and hydrolysis into the nontoxic O‐ethyl methylphosphonate 2. Magnesium monoperoxyphthalate (MMPP) is probably one of the most active reagents to achieve the complete detoxification of VX 1. The decontamination using MMPP was also extended with success to soman 13, a G‐type agent. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:485–490, 2001

A HTS Assay for the Detection of Organophosphorus Nerve Agent Scavengers

“…Similar HPLC experiments performed in parallel on PhX (3 b) at pH> 9.0 revealed significant amounts of the PÀO bond cleavage product, which is consistent with literature reports. [9][10][11][12] In the case of the fluorogenic probe 6, no traces of phosphonothioic acid were detected. As expected, the rate of hydrolysis of 6 is significantly accelerated under basic pH conditions because hydroxide ions are the active species during the spontaneous hydrolysis of the phosphonothioates.…”

“…Our library contained oximes (such as pralidoxime (2-PAM, 11) and its derivatives (12)(13)(14)(15)(16)(17)(18)(19), trimedoxime (TMB-4, 20), obidoxime (21) and HI-6 (22)) already known for their ability to reactivate OPNA-inhibited AChE. Their efficiencies were compared with those of other oximes and strong nucleophiles such as hydroxy-or mercaptopyridines, hydroxypyridinones, hydroxylamines, pyrimidines, hydroxamic acids, quinazolines and peracids.…”

“…The scavengers so far discovered range from metal-centred oxidation catalysts to engineered catalytic antibodies. [5] For now the most promising agents are still strong oxidants that act as a nucleophiles, [9][10][11][12] for example, hydrogen peroxide, peracids or oxidative chlorides or peroxides. The phosphorolytic reactivity of o-iodosylcarboxylates and related nucleophiles has also received a lot of interest, [13] yet such very efficient G nerve agent scavengers are poorly active towards V nerve agents.…”

Photocatalytic Destruction of a Thiosulfonate

“…TiO 2 was dried in an oven at 60°C overnight prior to the runs in pure acetonitrile. Diisopropylaminoethyl 4-methylbenzenethiosulfonate was synthesized according to the published procedure [16]. The synthesized product was recrystallized from methanol to remove the admixtures.…”

“…The chosen compound, diisopopylaminoethyl 4-methylbenzenethiosulfonate (DAMT) also simulates the structure and some properties of chemical warfare agent VX [16]. Structures of VX and DAMT are shown in figure 1.…”