Efficient Decontamination of Organophosphate-Based Pesticides and Nerve Agent Simulants Mediated by N‑Containing Nucleophiles.

There is a growing interest in developing safer and more effective decontaminating agents for organophosphate-based pesticides and nerve agents. In this study, we present an effective method for the nonaqueous decontamination of these compounds using small-molecule-based decontaminating agents under ambient conditions. Our approach utilizes aryl and heteroaryl carboxaldehyde hydrazones and hydrazides to effectively hydrolyze nerve agent simulants into their nontoxic degradation products. The effectiveness of this method was evaluated using a range of nerve agent simulants, including dimethyl 4-nitrophenyl phosphate (DMNP), dimethyl methylphosphonate (DMMP), and triphenyl phosphate (TPhP). In the presence of the heteroaryl hydrazone, the rate of hydrolysis was enhanced by 116-, 1930-, and 2490-fold relative to the uncatalyzed hydrolysis of TPhP, DMNP, and DMMP, respectively. Our findings demonstrate the potential of aryl carboxaldehyde hydrazones and hydrazides for the instantaneous and effective decontamination of nerve agents. These results are further substantiated by GIAO-DFT calculations. Additionally, the regioselectivity of the nucleophiles in the degradation of simulants to nontoxic products at alkaline pH (≥9.5) is elucidated.