Chlorpyrifos

Chlorpyrifos
Names
Preferred IUPAC name
O,O-Diethyl O-(3,5,6-trichloropyridin-2-yl) phosphorothioate
Other names
Brodan, Bolton insecticide, Chlorpyrifos-ethyl, Cobalt, Detmol UA, Dowco 179, Dursban, Empire, Eradex, Hatchet, Lorsban, Nufos, Paqeant, Piridane, Scout, Stipend, Tricel, Warhawk, others[1]
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.018.969
KEGG
PubChem CID
UNII
InChI
  • InChI=1S/C9H11Cl3NO3PS/c1-3-14-17(18,15-4-2)16-9-7(11)5-6(10)8(12)13-9/h5H,3-4H2,1-2H3 Y
    Key: SBPBAQFWLVIOKP-UHFFFAOYSA-N Y
  • InChI=1/C9H11Cl3NO3PS/c1-3-14-17(18,15-4-2)16-9-7(11)5-6(10)8(12)13-9/h5H,3-4H2,1-2H3
    Key: SBPBAQFWLVIOKP-UHFFFAOYAG
SMILES
  • Clc1c(OP(=S)(OCC)OCC)nc(Cl)c(Cl)c1
Properties
Chemical formula
 C9H11Cl3NO3PS
Molar mass 350.57 g·mol−1
Appearance Colorless crystals[2]
Odor Mercaptan-like[3]
Density 1.398 g/cm3 (43.5 °C)
Melting point 43 °C (109 °F; 316 K)[5]
Boiling point 160 °C; 320 °F; 433 K (decomposes)[3]
Solubility in water
 2 mg/L
log P 4.96 (octanol/water)[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 acute toxic, environmental hazard, combustible, reacts strongly with amines, strong acids, caustics[3]
Lethal dose or concentration (LD, LC):
  • 135 mg/kg (rat, oral)
  • 202 mg/kg (rat, dermal)[6]
NIOSH (US health exposure limits):
PEL (Permissible)
 none[3]
REL (Recommended)
 TWA 0.2 mg/m3 ST 0.6 mg/m3 [skin][3]
IDLH (Immediate danger)
 N.D.[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Chlorpyrifos (CPS), also known as chlorpyrifos ethyl, is an organophosphate pesticide that has been used on crops, animals, in buildings, and in other settings, to kill several pests, including insects and worms. It acts on the nervous systems of insects by inhibiting the acetylcholinesterase enzyme.[7][8] Chlorpyrifos was patented in 1966 by Dow Chemical Company.[9]

Chlorpyrifos is considered moderately hazardous to humans (Class II) by the World Health Organization based on acute toxicity information dating to 1999.[10] Exposure surpassing recommended levels has been linked to neurological effects, persistent developmental disorders, and autoimmune disorders. Exposure during pregnancy may harm the mental development of children.[11]

In the United Kingdom, the use of chlorpyrifos was banned as of 1 April 2016 (with one minor exception).[12] As of 2020, chlorpyrifos and chlorpyrifos-methyl were banned throughout the European Union, where they may no longer be used.[13] The EU also applied to have chlorpyrifos listed as a persistent organic pollutant under the Stockholm Convention on Persistent Organic Pollutants.[14] In May 2025, it actually got listed as a POP.[15]

As of August 18, 2021, the U.S. Environmental Protection Agency (EPA) announced a ban on the use of chlorpyrifos on food crops in the United States.[16][17][18] Most home uses of chlorpyrifos had already been banned in the U.S. and Canada since 2001.[11][19] It is banned in several other countries and jurisdictions as well. The chlorpyrifos ban on food crops is the result of a 1999 lawsuit filed by NRDC to force the EPA to take action on the riskiest pesticides, as well as five additional successful court orders obtained by Earthjustice to force the EPA to take action on a 2007 petition to ban chlorpyrifos filed by Natural Resources Defense Council and the Pesticide Action Network of North America (PANNA).[20]

  1. ^ "California Department of Pestidicide Regulation – Chlorpyrifos Product List May 2015" (PDF). Archived from the original (PDF) on 1 January 2019. Retrieved 30 March 2017.
  2. ^ Cite error: The named reference agrochemicals was invoked but never defined (see the help page).
  3. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0137". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ Sangster J; LOGKOW Databank. Sangster Res. Lab., Montreal Quebec, Canada (1994)
  5. ^ Lide, David R. (2015–2016). "Physical Constants of Organic Compounds". Handbook of Chemistry and Physics (96 ed.). Boca Raton, FL: CRC Press. pp. 3–122. ISBN 9781482208672.
  6. ^ "4Farmers Chlorpyrifos 500 Safety Data Sheet" (PDF). www.4farmers.com.au. Perth, Australia: 4Farmers Australia. 5 September 2016.
  7. ^ "Interactive MoA Classification". Insecticide Resistance Action Committee. 16 September 2020. Retrieved 1 April 2021.
  8. ^ Sparks, Thomas C.; Crossthwaite, Andrew J.; Nauen, Ralf; Banba, Shinichi; Cordova, Daniel; Earley, Fergus; Ebbinghaus-Kintscher, Ulrich; Fujioka, Shinsuke; Hirao, Ayako; Karmon, Danny; Kennedy, Robert; Nakao, Toshifumi; Popham, Holly J.R.; Salgado, Vincent; Watson, Gerald B.; Wedel, Barbara J.; Wessels, Frank J. (2020). "Insecticides, biologics and nematicides: Updates to IRAC's mode of action classification - a tool for resistance management". Pesticide Biochemistry and Physiology. 167. Elsevier: 104587. Bibcode:2020PBioP.16704587S. doi:10.1016/j.pestbp.2020.104587. ISSN 0048-3575. PMID 32527435. S2CID 218928832.
  9. ^ U.S. patent 3,244,586
  10. ^ World Health Organization (2019). The WHO Recommended Classification of Pesticides by Hazard and Guidelines to Classification 2019 (Report). World Health Organization.
  11. ^ a b Israel, Brett (21 August 2012). "Common Insecticide May Harm Boys' Brains More Than Girls". Scientific American.
  12. ^ "UK to ban sales and use of chlorpyrifos from April". Grainews. 30 March 2016. Retrieved 1 April 2022.
  13. ^ "EU-Wide ban of Chlorpyrifos and Chlorpyrifos-methyl". Eurofins Scientific. August 2020. Archived from the original on 16 June 2022. Retrieved 31 March 2022.
  14. ^ Meshkat, Nazanin (26 July 2021). "NGOs call on Health Canada to expedite ban on chlorpyrifos". The Globe and Mail. Retrieved 1 April 2022.
  15. ^ Krishnamurthy, Rohini (11 May 2025). "Countries list hazardous chlorpyrifos for elimination with 22 exemptions under Stockholm Convention". Down To Earth. Retrieved 5 May 2025.
  16. ^ Trager, Rebecca (27 August 2021). "US bans chlorpyrifos on all food crops". Chemistry World. Retrieved 31 March 2022.
  17. ^ Solomon, Gina (24 August 2021). "The EPA is banning chlorpyrifos, a pesticide widely used on food crops, after 14 years of pressure from environmental and labor groups". The Conversation. Retrieved 1 April 2022.
  18. ^ Romo, Vanessa (18 August 2021). "EPA Will Ban A Farming Pesticide Linked To Health Problems In Children". NPR. Retrieved 1 April 2022.
  19. ^ "Canada Quietly Bans Chlorpyrifos, While EPA's 60-Day Deadline For Action Rapidly Approaches". Beyond Pesticides Daily News Blog. 19 May 2021. Retrieved 1 April 2022.
  20. ^ April 20; Sass, 2022 Jennifer (20 April 2022). "EPA Bans Chlorpyrifos On Food Crops". NRDC. Retrieved 22 September 2022.{{cite web}}: CS1 maint: numeric names: authors list (link)
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