Chloropicrin
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Basic Info
| Common Name | Chloropicrin(F05479) |
| 2D Structure | |
| Description | Chloropicrin, also known as PS, is a chemical compound currently used as a broad-spectrum antimicrobial, fungicide, herbicide, insecticide, and nematicide. Chloropicrin can be absorbed systemically through inhalation, ingestion, and the skin. At high concentrations it is severely irritating to the lungs, eyes, and skin. In World War I German forces used concentrated chloropicrin against Allied forces as a tear gas. While not as lethal as other chemical weapons, it caused vomiting and forced Allied soldiers to remove their masks to vomit, exposing them to other, more toxic chemical gases used as weapons during the war. (Wikipedia) |
| FRCD ID | F05479 |
| CAS Number | 76-06-2 |
| PubChem CID | 6423 |
| Formula | CCl3NO2 |
| IUPAC Name | trichloro(nitro)methane |
| InChI Key | LFHISGNCFUNFFM-UHFFFAOYSA-N |
| InChI | InChI=1S/CCl3NO2/c2-1(3,4)5(6)7 |
| Canonical SMILES | C([N+](=O)[O-])(Cl)(Cl)Cl |
| Isomeric SMILES | C([N+](=O)[O-])(Cl)(Cl)Cl |
| Wikipedia | Chloropicrin |
| Synonyms |
Nitrotrichloromethane
CHLOROPICRIN
Trichloronitromethane
76-06-2
Chlorpikrin
Nitrochloroform
Trichlornitromethan
trichloro(nitro)methane
Chloropicrine
Dojyopicrin
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organohalogen compounds |
| Class | Alkyl halides |
| Subclass | Halomethanes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Trihalomethanes |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | C-nitro compound - Trihalomethane - Organic nitro compound - Organic oxoazanium - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Alkyl chloride - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organonitrogen compound - Organochloride - Organic oxygen compound - Organic nitrogen compound - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as trihalomethanes. These are organic compounds in which exactly three of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 164.366 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 79.9 |
| Monoisotopic Mass | 162.899 |
| Exact Mass | 162.899 |
| XLogP | 2.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 7 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Endives | Canada | 0.025mg/kg | |||
| Succulent Shelled Southern Peas | Canada | 0.025mg/kg | |||
| Amaranth | Canada | 0.025mg/kg | |||
| Apples | Canada | 0.025mg/kg | |||
| Apricots | Canada | 0.025mg/kg | |||
| Arracacha | Canada | 0.025mg/kg | |||
| Arrowroot | Canada | 0.025mg/kg | |||
| Arugula | Canada | 0.025mg/kg | |||
| Asian Pears | Canada | 0.025mg/kg | |||
| Asparagus | Canada | 0.025mg/kg | |||
| Balsam Apples | Canada | 0.025mg/kg | |||
| Balsam Pears | Canada | 0.025mg/kg | |||
| Bell Peppers | Canada | 0.025mg/kg | |||
| Black Salsify Roots | Canada | 0.025mg/kg | |||
| Blackberries | Canada | 0.025mg/kg | |||
| Blueberries | Canada | 0.025mg/kg | |||
| Bok Choy Chinese Cabbages | Canada | 0.025mg/kg | |||
| Broccoli | Canada | 0.025mg/kg | |||
| Broccoli Raab | Canada | 0.025mg/kg | |||
| Brussels Sprouts | Canada | 0.025mg/kg |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Effect of Soil Fumigation on Degradation of Pendimethalin and Oxyfluorfen inLaboratory and Ginger Field Studies. | J Agric Food Chem | 2016 Nov 23 | 27787973 |
| Emissions of 1,3-Dichloropropene and Chloropicrin after Soil Fumigation underField Conditions. | J Agric Food Chem | 2015 Jun 10 | 26001417 |
| Effect of co-formulation of 1,3-dichloropropene and chloropicrin on evaporativeemissions from soil. | J Agric Food Chem | 2015 Jan 21 | 25531174 |
| Brassica seed meal soil amendments transform the rhizosphere microbiome andimprove apple production through resistance to pathogen reinfestation. | Phytopathology | 2015 Apr | 25412009 |
| Effect of films on 1,3-dichloropropene and chloropicrin emission, soilconcentration, and root-knot nematode control in a raised bed. | J Agric Food Chem | 2013 Mar 13 | 23343207 |
| Evaluation of chloropicrin gelatin capsule formulation as a soil fumigant forgreenhouse strawberry in China. | J Agric Food Chem | 2012 May 23 | 22551154 |
| Iodine bonding stabilizes iodomethane in MIDAS pesticide. Theoretical study ofintermolecular interactions between iodomethane and chloropicrin. | J Agric Food Chem | 2012 Feb 22 | 22313191 |
| Interactive effect of organic amendment and environmental factors on degradation of 1,3-dichloropropene and chloropicrin in soil. | J Agric Food Chem | 2009 Oct 14 | 19722521 |
| Effects of manure and water applications on 1,3-dichloropropene and chloropicrin emissions in a field trial. | J Agric Food Chem | 2009 Jun 24 | 19459700 |
| Effect of drip application of ammonium thiosulfate on fumigant degradation insoil columns. | J Agric Food Chem | 2007 Oct 3 | 17848085 |
| Dechlorination of chloropicrin and 1,3-dichloropropene by hydrogen sulfidespecies: redox and nucleophilic substitution reactions. | J Agric Food Chem | 2006 Mar 22 | 16536608 |
| Dehalogenation of halogenated fumigants by polysulfide salts. | J Agric Food Chem | 2006 Jul 26 | 16848538 |
| Transformation of chloropicrin and 1,3-dichloropropene by metam sodium in acombined application of fumigants. | J Agric Food Chem | 2004 May 19 | 15137846 |
| Fumigation toxicity of volatile natural and synthetic cyanohydrins tostored-product pests and activity as soil fumigants. | Pest Manag Sci | 2004 Aug | 15307677 |
| Organic matter effects on phase partition of 1,3-dichloropropene in soil. | J Agric Food Chem | 2003 Jan 1 | 12502402 |
| Glucosinolate breakdown products as insect fumigants and their effect on carbondioxide emission of insects. | BMC Ecol | 2002 Mar 22 | 11914158 |
| Volatility, Adsorption, and Degradation of Propargyl Bromide as a Soil Fumigant. | J Agric Food Chem | 1998 Feb 16 | 10554310 |
| Rapid determination of fumigant and industrial chemical residues in food. | J Assoc Off Anal Chem | 1988 Jul-Aug | 3417594 |
Targets
- General Function:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]