DDT

For other uses, see DDT (disambiguation).

Dichlorodiphenyltrichloroethane
Chemical structure of DDT
Names
Preferred IUPAC name
1,1′-(2,2,2-Trichloroethane-1,1-diyl)bis(4-chlorobenzene)
Other names
Dichlorodiphenyltrichloroethane (DDT)
Clofenotane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.023 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C14H9Cl5/c15-11-5-1-9(2-6-11)13(14(17,18)19)10-3-7-12(16)8-4-10/h1-8,13H checkY
    Key: YVGGHNCTFXOJCH-UHFFFAOYSA-N checkY
  • InChI=1/C14H9Cl5/c15-11-5-1-9(2-6-11)13(14(17,18)19)10-3-7-12(16)8-4-10/h1-8,13H
    Key: YVGGHNCTFXOJCH-UHFFFAOYAJ
  • ClC1=CC=C(C(C(Cl)(Cl)Cl)C2=CC=C(C=C2)Cl)C=C1
Properties
C14H9Cl5
Molar mass 354.48 g·mol−1
Density 0.99 g/cm3
Melting point 108.5 °C (227.3 °F; 381.6 K)
Boiling point 260 °C (500 °F; 533 K) (decomposes)
25 μg/L (25 °C)[1]
Pharmacology
QP53AB01 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic, dangerous to the environment, suspected carcinogen
GHS labelling:
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H301, H350, H372, H410
P201, P202, P260, P264, P270, P273, P281, P301+P310, P308+P313, P314, P321, P330, P391, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 72–77 °C; 162–171 °F; 345–350 K[3]
Lethal dose or concentration (LD, LC):
113–800 mg/kg (rat, oral)[1]
250 mg/kg (rabbit, oral)
135 mg/kg (mouse, oral)
150 mg/kg (guinea pig, oral)[2]
NIOSH (US health exposure limits):[4]
PEL (Permissible)
 TWA 1 mg/m3 [skin]
REL (Recommended)
 Ca TWA 0.5 mg/m3
IDLH (Immediate danger)
 500 mg/m3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Dichlorodiphenyltrichloroethane, commonly known as DDT, is a colorless, tasteless, and almost odorless crystalline chemical compound,[5] an organochloride. Originally developed as an insecticide, it became infamous for its environmental impacts. DDT was first synthesized in 1874 by the Austrian chemist Othmar Zeidler. DDT's insecticidal action was discovered by the Swiss chemist Paul Hermann Müller in 1939. DDT was used in the second half of World War II to limit the spread of the insect-borne diseases malaria and typhus among civilians and troops. Müller was awarded the Nobel Prize in Physiology or Medicine in 1948 "for his discovery of the high efficiency of DDT as a contact poison against several arthropods".[6] The WHO's anti-malaria campaign of the 1950s and 1960s relied heavily on DDT and the results were promising, though there was a resurgence in developing countries afterwards.[7][8]

By October 1945, DDT was available for public sale in the United States. Although it was promoted by government and industry for use as an agricultural and household pesticide, there were also concerns about its use from the beginning.[9] Opposition to DDT was focused by the 1962 publication of Rachel Carson's book Silent Spring. It talked about environmental impacts that correlated with the widespread use of DDT in agriculture in the United States, and it questioned the logic of broadcasting potentially dangerous chemicals into the environment with little prior investigation of their environmental and health effects. The book cited claims that DDT and other pesticides caused cancer and that their agricultural use was a threat to wildlife, particularly birds. Although Carson never directly called for an outright ban on the use of DDT, its publication was a seminal event for the environmental movement and resulted in a large public outcry that eventually led, in 1972, to a ban on DDT's agricultural use in the United States.[10] Along with the passage of the Endangered Species Act, the United States ban on DDT is a major factor in the comeback of the bald eagle (the national bird of the United States) and the peregrine falcon from near-extinction in the contiguous United States.[11][12]

The evolution of DDT resistance and the harm both to humans and the environment led many governments to curtail DDT use.[13] A worldwide ban on agricultural use was formalized under the Stockholm Convention on Persistent Organic Pollutants, which has been in effect since 2004. Recognizing that total elimination in many malaria-prone countries is currently unfeasible in the absence of affordable/effective alternatives for disease control, the convention exempts public health use within World Health Organization (WHO) guidelines from the ban.[14]

DDT still has limited use in disease vector control because of its effectiveness in killing mosquitos and thus reducing malarial infections, but that use is controversial due to environmental and health concerns.[15][16] DDT is one of many tools to fight malaria, which remains the primary public health challenge in many countries. WHO guidelines require that absence of DDT resistance must be confirmed before using it.[17] Resistance is largely due to agricultural use, in much greater quantities than required for disease prevention.[17]

  1. ^ a b Cite error: The named reference ATSDRc5 was invoked but never defined (see the help page).
  2. ^ "DDT". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. ^ NIOSH Pocket Guide to Chemical Hazards. "#0174". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ "NIOSH Pocket Guide to Chemical Hazards".
  5. ^ Cite error: The named reference EHC009 was invoked but never defined (see the help page).
  6. ^ "The Nobel Prize in Physiology of Medicine 1948". Nobel Prize Outreach AB. Archived from the original on May 23, 2020. Retrieved July 26, 2007.
  7. ^ Cite error: The named reference DDTBP.1/2 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Feachem2007 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference Distillations was invoked but never defined (see the help page).
  10. ^ Lear, Linda (2009). Rachel Carson: Witness for Nature. Mariner Books. ISBN 978-0-547-23823-4. Archived from the original on October 19, 2021. Retrieved August 29, 2022.
  11. ^ Stokstad E (June 2007). "Species conservation. Can the bald eagle still soar after it is delisted?". Science. 316 (5832): 1689–1690. doi:10.1126/science.316.5832.1689. PMID 17588911. S2CID 5051469.
  12. ^ United States Fish and Wildlife Service, Fact Sheet: Natural History, Ecology, and History of Recovery [1] Archived May 21, 2020, at the Wayback Machine
  13. ^ Cite error: The named reference Chapin81 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference Stockholm was invoked but never defined (see the help page).
  15. ^ Larson K (December 1, 2007). "Bad Blood". On Earth (Winter 2008). Archived from the original on April 13, 2020. Retrieved June 5, 2008.
  16. ^ Moyers B (September 21, 2007). "Rachel Carson and DDT". Bill Moyers Journal. PBS. Archived from the original on April 25, 2011. Retrieved March 5, 2011.
  17. ^ a b Cite error: The named reference IRS-WHO was invoked but never defined (see the help page).