Mirex

Mirex

Names
Preferred IUPAC name Dodecachlorooctahydro-1H-1,3,4-(epimethanetriyl)cyclobuta[cd]pentalene
Identifiers
CAS Number	2385-85-5 Y
3D model ( JSmol )	Interactive image
ChEBI	CHEBI:34852 N
ChemSpider	16054 N
ECHA InfoCard	100.017.452
EC Number	236-948-9
KEGG	C14184 N
MeSH	D008917
PubChem CID	16945
UNII	Z917AN264P Y
CompTox Dashboard (EPA)	DTXSID7020895
InChI 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
SMILES ClC12C(C3(Cl)Cl)(Cl)C4(Cl)C1(Cl)C(Cl)(Cl)C5(Cl)C4(Cl)C3(Cl)C52Cl
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

Mirex is an

Mirex was first synthesized in 1946,[2] but was not used in pesticide formulations until 1955. Mirex was produced by the dimerization of hexachlorocyclopentadiene in the presence of aluminium chloride.

Mirex is a stomach insecticide, meaning that it must be ingested by the organism in order to poison it. The insecticidal use was focused on Southeastern United States to control the imported

Characteristic of chlorocarbons, mirex does not burn easily; combustion products are expected to include carbon dioxide, carbon monoxide, hydrogen chloride, chlorine, phosgene, and other organochlorine species. Slow oxidation produces chlordecone ("Kepone"), a related insecticide that is also banned in most of the western world, but more readily degraded. Sunlight degrades mirex primarily to photomirex (8-monohydromirex) and later partly to 2,8-dihydromirex.^[1][4][5]

• 
  Photomirex
• 
  2,8-dihydromirex

Mirex is highly resistant to microbiological degradation. It only slowly dechlorinates to a monohydro derivative by anaerobic microbial action in sewage sludge and by enteric bacteria. Degradation by soil microorganisms has not been described.

Bioaccumulation and biomagnification

Mirex is highly cumulative and amount depends upon the concentration and duration of exposure. There is evidence of accumulation of mirex in aquatic and terrestrial food chains to harmful levels. After 6 applications of mirex bait at 1.4 kg/ha, high mirex levels were found in some species; turtle fat contained 24.8 mg mirex/kg, kingfishers, 1.9 mg/kg, coyote fat, 6 mg/kg, opossum fat, 9.5 mg/kg, and racoon fat, 73.9 mg/kg. In a model ecosystem with a terrestrial-aquatic interface, sorghum seedlings were treated with mirex at 1.1 kg/ha. Caterpillars fed on these seedlings and their faeces contaminated the water which contained algae, snails, Daphnia, mosquito larvae, and fish. After 33 days, the ecological magnification value was 219 for fish and 1165 for snails.

Although general environmental levels are low, it is widespread in the biotic and abiotic environment. Being lipophilic, mirex is strongly adsorbed on sediments.

Safety

Mirex is only moderately toxic in single-dose animal studies (oral LD₅₀ values range from 365–3000 mg/kg body weight).^[6] It can enter the body via inhalation, ingestion, and via the skin. The most sensitive effects of repeated exposure in animals are principally associated with the liver, and these effects have been observed with doses as low as 1.0 mg/kg diet (0.05 mg/kg body weight per day), the lowest dose tested. At higher dose levels, it is fetotoxic (25 mg/kg in diet) and teratogenic (6.0 mg/kg per day). Mirex was not generally active in short-term tests for genetic activity. There is sufficient evidence of its carcinogenicity in mice and rats.^{[citation needed]} Delayed onset of toxic effects and mortality is typical of mirex poisoning.^{[citation needed]} Mirex is toxic for a range of aquatic organisms, with crustacea being particularly sensitive.

Mirex induces pervasive chronic physiological and biochemical disorders in various vertebrates. No acceptable daily intake (ADI) for mirex has been advised by FAO/WHO. IARC (1979) evaluated mirex's carcinogenic hazard and concluded that "there is sufficient evidence for its carcinogenicity to mice and rats. In the absence of adequate data in humans, based on above result it can be said, that it has carcinogenic risk to humans". Data on human health effects do not exist ^{[citation needed]}.

Health effects

Per a 1995