Chloropicrin
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Names | |||
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IUPAC name
Trichloro(nitro)methane
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Other names
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Identifiers | |||
3D model (
JSmol ) |
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1756135 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
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100.000.847 | ||
EC Number |
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240197 | |||
IUPHAR/BPS |
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KEGG | |||
PubChem CID
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RTECS number
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UNII | |||
UN number | 1580 | ||
CompTox Dashboard (EPA)
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Properties | |||
CCl3NO2 | |||
Molar mass | 164.375 g/mol | ||
Appearance | colorless liquid | ||
Odor | irritating[1] | ||
Density | 1.692 g/ml[2] | ||
Melting point | −69 °C (−92 °F; 204 K) | ||
Boiling point | 112 °C (234 °F; 385 K) (decomposes) | ||
0.2%[1] | |||
Vapor pressure | 18 mmHg (20°C)[1] | ||
−75.3·10−6 cm3/mol | |||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards
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Extremely toxic and irritating to skin, eyes, and lungs. Carcinogenic. | ||
GHS labelling: | |||
Danger | |||
H301, H314, H330, H370, H372, H410 | |||
P260, P264, P270, P271, P273, P280, P284, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P310, P314, P320, P321, P330, P363, P391, P403+P233, P405, P501 | |||
NFPA 704 (fire diamond) | |||
Lethal dose or concentration (LD, LC): | |||
LC50 (median concentration)
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9.7 ppm (mouse, 4 hr) 117 ppm (rat, 20 min) 14.4 ppm (rat, 4 hr)[3] | ||
LCLo (lowest published)
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293 ppm (human, 10 min) 340 ppm (mouse, 1 min) 117 ppm (cat, 20 min)[3] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
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TWA 0.1 ppm (0.7 mg/m3)[1] | ||
REL (Recommended)
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TWA 0.1 ppm (0.7 mg/m3)[1] | ||
IDLH (Immediate danger) |
2 ppm[1] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chloropicrin, also known as PS (from
Synthesis
Chloropicrin was discovered in 1848 by Scottish chemist John Stenhouse. He prepared it by the reaction of sodium hypochlorite with picric acid:
Because of the precursor used, Stenhouse named the compound chloropicrin, although the two compounds are structurally dissimilar.
Today, chloropicrin is manufactured by the reaction of nitromethane with sodium hypochlorite:[7]
- H3CNO2 + 3 NaOCl → Cl3CNO2 + 3 NaOH
Properties
Chloropicrin's chemical formula is CCl3NO2 and its molecular weight is 164.38 grams/mole.
Use
Chloropicrin was manufactured for use as
Chloropicrin is used as an indicator and repellent when fumigating residences for insects with sulfuryl fluoride which is an odorless gas.[13] Chloropicrin's mode of action is unknown[14] (IRAC MoA 8B).[15] Chloropicrin may stimulate weed germination, which can be useful when quickly followed by a more effective herbicide.[16]In February 2024,
Safety
At a national level, chloropicrin is regulated in the United States by the United States Environmental Protection Agency as a restricted use pesticide.[10][21] Because of its toxicity and carcinogenicity, distribution and use of chloropicrin is available only to licensed professionals and specially certified growers who are trained in its proper and safe use.[10][21] In the US, occupational exposure limits have been set at 0.1 ppm over an eight-hour time-weighted average.[22]
Agriculture
In 2008 the US
Used as a preplant soil treatment measure, chloropicrin suppresses soilborne pathogenic
California
In
High concentrations
Chloropicrin is harmful to humans. It can be absorbed systemically through inhalation, ingestion, and the skin. At high concentrations, it is severely irritating to the lungs, eyes, and skin.
Damage to protective gear
Chloropicrin and its derivative phosgene oxime have been known to damage or compromise earlier generations of personal protective equipment. Some of the soldiers attacked mentioned a white smoke emerging from their gas masks.[citation needed]
See also
References
- ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0132". National Institute for Occupational Safety and Health (NIOSH).
- ^ http://msds.chem.ox.ac.uk/CH/chloropicrin.html [dead link]
- ^ a b "Chloropicrin". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ Foulkes, C.H. (31 Jan 2012). "GAS!" — The Story of the Special Brigade. Andrews UK Limited. p. 193.
- ^ "RED Fact Sheet: Chloropicrin" (PDF). US Environmental Protection Agency. 10 July 2008. p. 2. Retrieved 20 September 2013.
- ^ Murphy, Matt (May 2, 2024). "Russia using chemical choking agents in Ukraine, US says". BBC News. Retrieved May 3, 2024.
- ^ Sheldon B. Markofsky "Nitro Compounds, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
- ^ a b c d e f "Executive Summary - Evaluation of Chloropicrin As A Toxic Air Contaminant" (PDF). Department of Pesticide Regulation - California Environmental Protection Agency. February 2010. p. iv. Archived from the original (PDF) on 6 October 2013. Retrieved 20 September 2013.
- ^ Ayres, Leonard P. (1919). The War with Germany (Second ed.). Washington, DC: United States Government Printing Office. p. 80.
- ^ a b c d "Chloropicrin – Background". Retrieved 20 September 2013.
- ^ a b "Factsheet: Chloropicrin" (PDF). www.workcover.nsw.gov.au. Archived from the original (PDF) on May 20, 2009.
- ^ Amos Alfred Fries; Clarence Jay West (1921). Chemical warfare. McGraw-Hill book company, inc. p. 144.
- ^ "Vikane® gas fumigant – Trusted by Homeowners, Preferred by Professionals".
- ^ Chloropicrin in the Pesticide Properties DataBase (PPDB), University of Hertfordshire, accessed 2021-03-10.
- ^ "IRAC Mode of Action Classification Scheme Version 9.4". IRAC (Insecticide Resistance Action Committee) (pdf). March 2020.
- PMID 14527332.
- ^ "Ukraine accuses Russia of intensifying chemical attacks on the battlefield". Reuters. Retrieved 2024-02-10.
- ^ "Imposing New Measures on Russia for its Full-Scale War and Use of Chemical Weapons Against Ukraine". United States Department of State. Retrieved 2 May 2024.
- ^ "Russians Use Banned Chemical Weapons in Donbas, Killing Ukrainian Military and Polluting the Environment". Cyprus Daily News. 6 May 2024.
- ^ "Ukraine Situation Report: Polish MiG-29s Delivered". The Warzone. 6 May 2024.
- ^ a b "Chloropicrin Mitigation Proposal" (PDF). Department of Pesticide Regulation – California Environmental Protection Agency. 15 May 2013. p. 1. Archived from the original (PDF) on 6 October 2013. Retrieved 20 September 2013.
- ^ "NIOSH Pocket Guide to Chemical Hazards". Centers for Disease Control and Prevention. Retrieved 7 November 2013.
- ^ "Amended Reregistration Eligibility Decision (RED) for Chloropicrin" (PDF). United States Environmental Protection Agency. May 2009. Retrieved 20 September 2013.
- ^ a b "Chloropicrin Mitigation Proposal" (PDF). Department of Pesticide Regulation – California Environmental Protection Agency. 15 May 2013. p. 2. Archived from the original (PDF) on 6 October 2013. Retrieved 20 September 2013.
- ^ a b "Environmental Protection Agency (EPA) Re-Registers Chloropicrin As Safe For Use Nationwide". Retrieved 22 October 2013.
- ^ "Chloropicrin Mitigation Proposal" (PDF). Department of Pesticide Regulation – California Environmental Protection Agency. 15 May 2013. p. 2. Archived from the original (PDF) on 6 October 2013. Retrieved 20 September 2013.
The Amended RED incorporated final new safety measures to increase protections for agricultural workers and bystanders. These measures establish a baseline for safe use of the soil fumigants throughout the United States, reducing fumigant exposures and significantly improving safety.
- ^ "Chloropicrin – Frequently Asked Questions". Retrieved 21 October 2013.
- ^ "Chloropicrin Soil Fumigation in Potato Production Systems". Plant Management Network. American Phytopathological Society. Retrieved 1 Apr 2019.
- ^ "Control Measures for Chloropicrin" (PDF). California Department of Pesticide Regulation. January 6, 2015. Archived from the original (PDF) on January 28, 2015. Retrieved January 15, 2015.
added controls for chloropicrin when it is used as a soil fumigant. The controls are intended to reduce risk from acute (short-term) exposures that might occur near fields fumigated with products containing chloropicrin.
- ^ "Chloropicrin Mitigation Proposal" (PDF). Department of Pesticide Regulation – California Environmental Protection Agency. 15 May 2013. p. 2. Archived from the original (PDF) on 6 October 2013. Retrieved 20 September 2013.
The new measures appearing on soil fumigant Phase 2 labels include buffer zones and posting, emergency preparedness and response measures, training for certified applicators supervising applications, Fumigant Management Plans, and notice to State Lead Agencies who wish to be informed of applications in their states.
- ^ Chloropicrin (PS): Lung Damaging Agent. National Institute for Occupational Safety and Health. Emergency Response Safety and Health Database, August 22, 2008. Retrieved December 23, 2008.
- ^ Heller, Charles E. (September 1984). "Chemical Warfare in World War I: The American Experience, 1917-1918" (PDF). Leavenworth Papers (10): 23.