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Paraquat information


Paraquat
Names
Preferred IUPAC name
1,1′-Dimethyl[4,4′-bipyridine]-1,1′-diium dichloride
Other names
Paraquat dichloride; Methyl viologen dichloride; MVCl2; Crisquat; Dexuron; Esgram; Gramuron; Ortho Paraquat CL; Para-col; Pillarxone; Tota-col; Toxer Total; PP148; Cyclone; Gramixel; Gramoxone; Pathclear; AH 501; Bai Cao Ku.
Identifiers
CAS Number
  • 1910-42-5 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28786 checkY
ChEMBL
  • ChEMBL458019 checkY
ChemSpider
  • 15146 checkY
ECHA InfoCard 100.016.015 Edit this at Wikidata
IUPHAR/BPS
  • 4552
PubChem CID
  • 15938
UNII
  • 2KZ83GSS73 checkY
CompTox Dashboard (EPA)
  • DTXSID7024243 Edit this at Wikidata
InChI
  • InChI=1S/C12H14N2.2ClH/c1-13-7-3-11(4-8-13)12-5-9-14(2)10-6-12;;/h3-10H,1-2H3;2*1H/q+2;;/p-2 checkY
    Key: FIKAKWIAUPDISJ-UHFFFAOYSA-L checkY
  • InChI=1/C12H14N2.2ClH/c1-13-7-3-11(4-8-13)12-5-9-14(2)10-6-12;;/h3-10H,1-2H3;2*1H/q+2;;/p-2/fC12H14N2.2Cl/h;2*1h/qm;2*-1
  • InChI=1/C12H14N2.2ClH/c1-13-7-3-11(4-8-13)12-5-9-14(2)10-6-12;;/h3-10H,1-2H3;2*1H/q+2;;/p-2
    Key: FIKAKWIAUPDISJ-NUQVWONBAF
SMILES
  • C[n+]1ccc(cc1)c2cc[n+](cc2)C.[Cl-].[Cl-]
Properties
Chemical formula
C12H14Cl2N2
Molar mass 257.16 g·mol−1
Appearance Yellow solid[1]
Odor faint, ammonia-like[1]
Density 1.25 g/cm3
Melting point 175 to 180 °C (347 to 356 °F; 448 to 453 K)[2]
Boiling point > 300 °C (572 °F; 573 K)[2]
Solubility in water
High
Vapor pressure <0.0000001 mmHg (20 °C)[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic, environmental hazard
GHS labelling:
Pictograms
GHS06: Toxic GHS08: Health hazard GHS09: Environmental hazard
Hazard statements
H301, H311, H315, H319, H330, H335, H372, H410[3]
Precautionary statements
P260, P273, P280, P284, P301+P310, P305+P351+P338
Lethal dose or concentration (LD, LC):
LD50 (median dose)
57 mg/kg (rat, oral)
120 mg/kg (mouse, oral)
25 mg/kg (dog, oral)
22 mg/kg (guinea pig, oral)[4]
LC50 (median concentration)
3 mg/m3 (mouse, 30 min respirable dust)
3 mg/m3 (guinea pig, 30 min respirable dust)[4]
LCLo (lowest published)
1 mg/m3 (rat, respirable dust, 6 h)
6400 mg/m3 (rat, nonrespirable dust, 4 h)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 0.5 mg/m3 (resp) [skin][1]
REL (Recommended)
TWA 0.1 mg/m3 (resp) [skin][1]
IDLH (Immediate danger)
1 mg/m3[1]
Safety data sheet (SDS) Aldrich MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Paraquat (trivial name; /ˈpærəkwɒt/), or N,N′-dimethyl-4,4′-bipyridinium dichloride (systematic name), also known as methyl viologen, is an organic compound with the chemical formula [(C6H7N)2]Cl2. It is classified as a viologen, a family of redox-active heterocycles of similar structure.[5] This salt is one of the most widely used herbicides. It is quick-acting and non-selective, killing green plant tissue on contact. It is also toxic (lethal) to human beings and animals due to its redox activity, which produces superoxide anions. It has been linked to the development of Parkinson's disease[6][7] and is banned in 58 countries.[8][9]

Paraquat may be in the form of salt with chloride or other anions; quantities of the substance are sometimes expressed by cation mass alone (paraquat cation, paraquat ion).

The name is derived from the para positions of the quaternary nitrogens.

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0478". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b "Paraquat dichloride". International Programme on Chemical Safety. October 2001. Archived from the original on 2010-12-19. Retrieved 2007-09-06.
  3. ^ Sigma-Aldrich Co., 1,1′-Dimethyl-4,4′-bipyridinium dichloride hydrate. Retrieved on 2015-03-29.
  4. ^ a b c "Paraquat". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^ In 1932, the German-American chemist Leonor Michaelis (1875–1949) named paraquat "methyl viologen" and used it as an indicator in redox reactions. See:
    • Michaelis, L. (1932). "Ein Reduktions-Indikator im Potentialbereich der Wasserstoffüberspannung" [A reduction indicator in the voltage range of hydrogen overpotential]. Biochemische Zeitschrift (in German). 250: 564–567.
    • See also: Michaelis, L.; Hill, Edgar S. (1933). "The viologen indicators" (PDF). The Journal of General Physiology. 16 (6): 859–873. doi:10.1085/jgp.16.6.859. PMC 2141252. PMID 19872744. Archived (PDF) from the original on 2019-08-16. Retrieved 2019-08-16.
  6. ^ "Two pesticides—rotenone and paraquat—linked to Parkinson's disease, study suggests". Science Daily. 2011. Archived from the original on April 26, 2019. Retrieved October 25, 2011.
  7. ^ Kamel, F. (2013). "Paths from Pesticides to Parkinson's". Science. 341 (6147): 722–723. Bibcode:2013Sci...341..722K. doi:10.1126/science.1243619. PMID 23950519. S2CID 11119082. Archived from the original on 2018-11-27. Retrieved 2018-09-13.
  8. ^ "This weed killer is banned in 50 countries. U.S. workers say it's giving them Parkinson's". Los Angeles Times. 2023-12-20. Archived from the original on 2023-12-20. Retrieved 2023-12-21.
  9. ^ "'Burns me to a crisp': Farmers allege link between popular herbicide paraquat and Parkinson's disease - ABC News". 2023-11-28.

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