Mirex

Mirex
Mirex
Ball-and-stick model
Names
Preferred IUPAC name
Dodecachlorooctahydro-1H-1,3,4-(epimethanetriyl)cyclobuta[cd]pentalene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.017.452 Edit this at Wikidata
EC Number
  • 236-948-9
KEGG
MeSH D008917
UNII
  • InChI=1S/C10Cl12/c11-1-2(12)7(17)4(14)3(13,5(1,15)9(7,19)20)6(1,16)10(21,22)8(2,4)18 ☒N
    Key: GVYLCNUFSHDAAW-UHFFFAOYSA-N ☒N
  • InChI=1/C10Cl12/c11-1-2(12)7(17)4(14)3(13,5(1,15)9(7,19)20)6(1,16)10(21,22)8(2,4)18
    Key: GVYLCNUFSHDAAW-UHFFFAOYAV
  • ClC12C(C3(Cl)Cl)(Cl)C4(Cl)C1(Cl)C(Cl)(Cl)C5(Cl)C4(Cl)C3(Cl)C52Cl
Properties
C10Cl12
Molar mass 545.55 g/mol
Melting point 485 °C (905 °F; 758 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Mirex is an organochloride that was commercialized as an insecticide and later banned because of its impact on the environment. This white crystalline odorless solid is a derivative of cyclopentadiene. It was popularized to control fire ants but by virtue of its chemical robustness and lipophilicity it was recognized as a bioaccumulative pollutant. The spread of the red imported fire ant was encouraged by the use of mirex, which also kills native ants that are highly competitive with the fire ants. The United States Environmental Protection Agency prohibited its use in 1976.[1] It is prohibited by the Stockholm Convention on Persistent Organic Pollutants.

  1. ^ Robert L. Metcalf "Insect Control" in Ullmann’s Encyclopedia of Industrial Chemistry" Wiley-VCH, Wienheim, 2002. doi:10.1002/14356007.a14_263