Mirex
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IUPAC name
1,1a,2,2,3,3a,4,5,5,5a,5b,6-dodecachlorooctahydro-1H-1,3,4-(methanetriyl)cyclobuta[cd]pentalene
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| Identifiers | |
2385-85-5 
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| 3D model (Jmol) | Interactive image |
| ChEBI |
CHEBI:34852 
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| ChemSpider |
16054
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| ECHA InfoCard | 100.017.452 |
| EC Number | 236-948-9 |
| KEGG |
C14184
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| MeSH | D008917 |
| PubChem | 16945 |
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| Properties | |
| C10Cl12 | |
| Molar mass | 545.55 g/mol |
| Melting point | 485 °C (905 °F; 758 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is ?) |
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| Infobox references | |
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. Ironically, the spread of the red imported fire ant was actually 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.
Mirex was first synthesized in 1946, 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 fire ants Solenopsis saevissima richteri and Solenopsis invicta. Approximately 250,000 kg of mirex was applied to fields between 1962-75 (US NRC, 1978). Most of the mirex was in the form of "4X mirex bait," which consists of 0.3% mirex in 14.7% soybean oil mixed with 85% corncob grits. Application of the 4X bait was designed to give a coverage of 4.2 g mirex/ha and was delivered by aircraft, helicopter or tractor. 1x and 2x bait were also used. Use of mirex as a pesticide was banned in 1978. The banned production and use of several persistent organic pollutant, and Mirex is one of the "dirty dozen".
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.
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Wikipedia