Pentalene, octahydro

Mitex [2385-85-5] is l,2,3,4,5,5,6,7,8,9,10,10-dodecachloro-octahydro-l,3,4-metheno-2JT-cyclobuta-p,<7 -pentalene (37) (mp 485°C). The rat LD s are 306, 600 (oral) and >2000 (dermal) mg/kg. Mirex is extremely resistant to biodegradation and was once considered the perfect stomach poison iasecticide for use ia baits to control imported fire ants. However, even at doses of a few milligrams per 10 m it was found to bioaccumulate ia birds and fish and its registrations were canceled ia the United States ia 1976. 

The pesticides included in this study were fenvalerate, chlordecone (kepone), chlorothalonil, and chlorpyrifos. Fenvalerate is a synthetic pyrethroid insecticide used, for example, for mites on chickens. Its chemical name is cyano(3-phenoxyphenyl)-methyl 4-chloro-alpha-(1-methylethyl)benzeneacetate. Chlordecone is an insecticide, no longer used, and has a chemical name decachloro-octahydro-l,3,4-metheno-2H-cyclobuta(cd)=pentalen-2-one. Chlorothalonil is fungicide used on tomatoes whose chemical name is 2,4,5,6-tetrachloroisophthalonitrile. Chlorpyrifos is an insecticide with a chemical name 0,0-diethyl 0-(3,5,6-trichloro-2-pyridyl)phosphorothioate. Chlorpyrifos is the U. S. Food and Drug Administration chromatographic reference standard since numerous specific detectors (electron capture, flame photometric in both sulfur and phosphorus modes, alkali flame, nitrogen phosphorus, and Hall detectors) are sensitive to it. 

Chemical Name l,la,2,2,3,3a,4,5,5,5a,5b,6-dodecachloro-octahydro-l,3,4-methano-lH-cyclobuta(cd) pentalene ... 

METHANO-2H-CYCLOBUTA(CD)PENTALEN-2-ONE 1.1 A3,3A4.5.5.5A5B.6- DECACHLOROCTAHYDRO-1,1 A3,3A.4.5.5A,5B.6-DECACHLORO-OCTAHYDRO-1. 3.4-METHENO-2H-CYCLO... 

Mirex is a white, odorless, free-flowing, crystalline, nonflammable, polycyclic com-poimd composed entirely of carbon and chlorine the empirical formula is C10CI12, and the molecular weight 545.54. In the U.S., the common chemical name is dodecachloro-octahydro-1,3,4-metheno-2H-cyclobuta (c,d) pentalene the systematic name is dode-cachloropentacyclo 5.3.0.0 . 0 . 0 decane (Figure 20.1). Mirex was first prepared in 1946, patented in 1955 by Allied Chemical Company, and introduced in 1959 as GC 1283 for use in pesticidal formulations against hymenopterous insects, especially ants. It was also marketed under the trade name of Dechlorane for use in flame-retardant coatings for various materials. Mirex is also known as ENT 25719, CAS 2385-85-5, Dechlorane 510, and Dechlorane 4070. 

Representative procedure synthesis of (3aa,5aP,8a -I,2,3a,5,5a,6,7,8-octahydro-2,2-dimethylcyclopenta[c]pentalene-3,4-dion ... 

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