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Brief History and Use of Chemical Warfare Agents in Warfare and Terrorism
Published in Brian J. Lukey, James A. Romano, Salem Harry, Chemical Warfare Agents, 2019
Harry Salem, Andrew L. Ternay Jr., Jeffery K. Smart
Chloropicrin or trichloronitromethane (CCl3NO2) was prepared in 1848 by Stenhouse and was extensively used in World War I. A pungent, colorless, oily liquid, it caused oral–nasal irritation, coughing, and vomiting. In high dosages, it caused lung damage and pulmonary edema. It was first employed dissolved in sulfuryl chloride by the Russians in 1916 in hand grenades. In Germany it was known as Klop, in France as Aquinite, and as PS in the United States. It was later used as an insecticide and fungicide as well as for eradicating rats from ships (Sartori, 1943).
Pesticides and Chronic Diseases
Published in William J. Rea, Kalpana D. Patel, Reversibility of Chronic Disease and Hypersensitivity, Volume 4, 2017
William J. Rea, Kalpana D. Patel
Chloroform, carbon tetrachloride, methyl bromide (MeBr; Fumigant-1, Kayafume, Meth-O-Gas, Pestmaster, ProFume), chloropicrin (Acquinte, Chlor-O-Pic, Pic-Clor, Picfume, Tri-Clor), ethylene dichloride (EDC), ethylene dibromide (EDB, Bromofume, Celmide, Dowfume W-85, Kop-Fume, Nephis, Pestmaster EDB-85, Soilbrom), dichloropropene and dichloropropane (Telone, D-D), sulfuryl fluoride (Vikane), and dibromochloropropane (DBCP) are known common fumigants (Figures 7.64 and 7.65).
Neurotoxicity of Pesticides
Published in Ana Maria Osorio, Lynn R. Goldman, Proceedings from the Medical Workshop on Pesticide-Related Illnesses from the International Conference on Pesticide Exposure and Health, 2017
Matthew C. Keifer, Jordan Firestone
Sulfuryl fluoride has been less frequently reported as an acute central nervous system intoxicant.27,28 However, two epidemiological studies have demonstrated chronic central nervous system deficits associated with chronic exposure to sulfuryl fluoride in pesticide applicators.29,30
Covalent drug discovery using sulfur(VI) fluoride exchange warheads
Published in Expert Opinion on Drug Discovery, 2023
In 1930, aryl fluorosulfates were first synthesized by the pyrolysis of arenediazonium fluorosulfate salts [75]. From the 1960s to 1980s, multiple groups combined the appropriate phenol (or phenolate) with fluorosulfonic anhydride [76], sulfuryl chloride fluoride [77], or sulfuryl fluoride (SO2F2) in the presence of a base at low temperature to generate sulfonyl fluorides [78]. However, these methods either require highly toxic and/or expensive reagents or dangerous reaction procedures (e.g. gas condensation) which often results in low yields. In 2014, the Sharpless group reported a robust and high-yielding process for the preparation of fluorosulfates from the reaction of phenols with sulfuryl fluoride in the presence of Et3N [14]. In general, SO2F2 gas was introduced via a balloon after the reaction flask was septum sealed, but the application of the gas was limited by the small number of suppliers. The Borggraeve group recently reported an ex situ generation method of SO2F2 and a commercially available 2-chamber reactor can be applied to facilitate the reaction set-up [79]. SO2F2 can be efficiently generated from the reaction of 1,1’-sulfonyldiimidazole (SDI) with KF (Figure 4b) and then the corresponding fluorosulfates can be obtained by the reaction of SO2F2 with phenols in the presence of a base. Although SO2F2 is a robust reagent for the synthesis of fluorosulfates, it is a toxic gas requiring specialized equipment, indicating a need to develop a safe and convenient replacement. A shelf-stable, user-friendly crystalline reagent called [4-(acetylamino)phenyl]imidodisulfuryl difluoride (AISF) was developed to achieve the synthesis of a diverse array of aryl fluorosulfates under mild conditions (Figure 4b) [80].