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Chlordane
Chlordane
Chlordane
IUPAC name
Other names Chlordan, Ortho
Identifiers
CAS number 57-74-9
PubChem 5993
SMILES
Properties
Molecular formula C10H6Cl8
Molar mass 409.779 g/mol
Density 1.60 g/cm3
Melting point

106 °C

Boiling point

175 °C at 1 mmHg[1]

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Chlordane, or chlordan, is an organochlorine compound that was used as a pesticide. This white solid was sold in the U.S. until 1983 as an insecticide for crops like corn and citrus and on lawns and domestic gardens. [2]

Contents

Production and uses

Chlordane is one so-called cyclodiene pesticide, meaning that it is derived from hexachlorocyclopentadiene. Hexachlorocyclopentadiene forms an adduct with cyclopentadiene, and chlorination of this adduct give two isomers, α and β. The mixture is called chlordane. The β isomer is more bioactive.[2] It was sold in the United States from 1948 to 1988 both as a dust and an emulsified solution.

Because of concern about damage to the environment and harm to human health, the United States Environmental Protection Agency (EPA) banned all uses of chlordane in 1983 except termite control. The EPA banned all uses of chlordane in 1988. The EPA recommends that children should not drink water with more than 60 parts of chlordane per billion parts of drinking water (60 ppb) for longer than 1 day. EPA has set a limit in drinking water of 2 ppb.

Environmental impact

Being hydrophobic, chlordane adheres to soil particles and enters groundwater only slowly owing to its low solubility (0.009 ppm). It degrades only over the course of years.[3] Chlordane bioaccumulates in animals. It is highly toxic to fish, with an LD50 of 0.022–0.095 mg/kg (oral).

Health effects

Exposure to chlordane metabolites may be associated with testicular cancer. The incidence of seminoma in men with the highest blood levels of cis-nonachlor was almost double that of men with the lowest levels.[4] Prostate cancer has been associated with trans-nonachlor levels, a component of chlordane.[5] Japanese workers who used chlordane over a long period of time had minor changes in liver function.[6]

References

  1. ^ Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, FL: CRC Press, pp. 3–100, ISBN 0849305942  
  2. ^ a b Robert L. Metcalf “Insect Control” in Ullmann’s Encyclopedia of Industrial Chemistry” Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a14_263
  3. ^ http://organic.com.au/pesticides/Chlorodane/
  4. ^ McGlynn, Katherine A.; Quraishi, Sabah M.; et al. (April 29, 2008), "Persistent Organochlorine Pesticides and Risk of Testicular Germ Cell Tumors", Journal of the National Cancer Institute published ahead of print: 663, doi:10.1093/jnci/djn101, http://jnci.oxfordjournals.org/cgi/content/abstract/djn101v1  .
  5. ^ http://www.ehponline.org/members/2009/0900919/0900919.pdf doi:10.1289/ehp.0900919
  6. ^ http://www.atsdr.cdc.gov/tfacts31.html

External links

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