Metheno

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. 

This reaction can also be used for the synthesis of substituted 1-benzoxepins with one modification instead of the 4/T-benzopyran the 2/7-isomer must be used. 2-[Diazo(phosphoryl)meth-yl]-2//-benzopyrans decompose in the presence of ))3-allylpalladium chloride dimer with elimination of nitrogen to give 1-benzoxepins 2.192 In some cases, the reaction takes a different course and gives 2-methylene-2//-benzopyrans 3.192 In this respect, the bicyclic system behaves differently to the monocyclic diazo(pyranyl)methane. The 2-isomers of the latter structure could not be isolated and gave l//-l,2-diazepines.190 The 4//-benzopyrans do not form benzoxepins but undergo an intramolecular [2+1] cycloaddition to 3,4-dihydro-2,3,4-metheno-2//-ben-... 

Mirex is a white, odorless, free-flowing, crystalline, nonflammable, polycyclic compound composed entirely of carbon and chlorine. The empirical formula is C10C112, and the molecular weight 545.54 (Hyde 1972 Waters et al. 1977 Bell et al. 1978 NAS 1978 Menzie 1978 Kaiser 1978). In the United States, the common chemical name is dodecachlorooctahydro-l,3,4-metheno-2H-cyclobuta[c,systematic name is dodecachloropentacyclo 5.3.0.02-6.03 9.04 8decane. Mirex was first prepared in 1946, patented in 1955 by Allied Chemical Company, and introduced... 

Mirex (dodecachlorooctahydro-l,3,4-metheno-2H-cyclobuta [tv/] pentalene) has been used extensively in pesticidal formulations to control the red imported fire ant (Solenopsis invicta), and as a flame retardant in electronic components, plastics, and fabrics. One environmental consequence of mirex was the severe damage recorded to fish and wildlife in nine southeastern states and the Great Lakes, especially Lake Ontario. In 1978, the U.S. Environmental Protection Agency banned all further use of mirex, partly because of the hazards it imposed on nontarget biota. These included ... 

Hexachloro-1,3-cyclopentadiene dimerb dodecachlorooctahydro-1,3,4-metheno-1 H-cyclobuta[cd] pentaleneb... 

EPA. 1986f. Revocation of dodecachlorooctahydro-1,3,4-metheno-2H-cyclobuta[cd] pentalene tolerances. U.S. Environmental Protection Agency. Federal Register 51 45114-45115.d->f... 

Uk S, Himel CM, Dirks TF. 1972. Mass spectral pattern of mirex (dodecachlorooctahydro-1,3,4-metheno-2H-cyclobuta (cd) pentalene) and of Kepone (decachlorooctahydro-1,3,4-metheno-2H-cyclobuta (cd)- pentalen-2-one) and its application in residue analysis. Bull Environ Contam Toxicol 7(4) 207-215. 

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. 

Synonyms AI3-16391 Caswell No. 275 C-01792 CCRIS 128 Chlordecone CIBA 8514 Clor-decone Compound 1189 l,2,3,5,6,7,8,9,10,10-Decachloro[5.2.1.0 .0 .0 ]decano-4-one Deca-hloroketone Decachloro-l,3,4-metheno-2//-cyclobuta[cc/ pentalen-2-one Decachlorooctahydro-kepone-2-one Decachlorooctahydro-l,3,4-metheno-2//-cyclobuta[cc/ pentalen-2-one Decachloro-... 

Decachlorooctahydro-1,3,4-metheno-2H-cyclobuta[c,d]-pentalen-2-one (Kepone, chlordecone)... 

Allied Chemical Corporation Toxicological studies on decachlorooctahydro-1,3,4-metheno-2//-cyclobuta[cd] pentalen-2 -one (Compound no. 1189) (Kepone). New York, Allied Chemical Corporation, March 1960... 

DOMIRO DIELS-ALDER REACTION 3,3a,3b.4.6a.7a-HEXAHYDR0-3,4,7-METHENO-7H-CYCLOPENTA[a]PENTALEN -7,8-DICARBOXYLIC ACID (3,4,7-Netheno-7H-c3rc1 openta[a]penta1 ene-7.8-dlcarbofyllc add, 3,3a,3b,4,6a,7a-hexahydro-)... 

Dimethyl 3,3a,3b,4,6a,7a-hexahydro-3,4,7-metheno-7H-cyclopenta[a]pentalene-7,8-d1carboxyl ate 3,4,7-Hetheno-7H-cyclopenta[a]pentalene-7,8-di carboxylic acid, 3,3a,3b,4,6a,7a-hexahydro-, dimethyl ester (9) (53282-97-6)... 

Chemical Abstracts has developed the use of method b to quite a high level of sophistication. Trivalent (e.g., metheno) and tetravalent units and many ring systems can be cited as bridging groups, e.g., 39-41. 

Dimethyl 3,3a,3b,4,6a,7a-hexahydro-3,4,7-metheno-7H-cyclopenta[a]pentalene-7,8-dicarboxylate 3,4,7-Metheno-7H-cyclopenta[a]pentalene-7,8-dicarboxylic acid, 3,3a,3b,4,6a,7a-hexahydro-, dimethyl ester (53282-97-6), 68, 198 Dimethyl (E)-2-hexenedioate (70353-99-0), 66, 52, 53, 59 N,0-Dimethylhydroxylamine hydrochloride Methylamine, N-methoxy-, hydrochloride Methanamine, N-methoxy-, hydrochloride (6638-79-5), 67, 69 N,N-Dimethylisobutyramide, 66, 117, 118... 

DODECACHLOROOCTAHYDRO-1.3.4-METHENO-1H-CYCLOBUTA(c,d)PENTALENE DODECA-CHLOROPENTACYCLODECANE DODECACHLORO-PENTACYCLO(3,2,2,o2.6 o3.9,o5.10)DECANE ENT 25,719 FERRIAMICIDE HEXACHLOROCYCLOPENTADI-ENEDIMER l,2,3,4,5,5-HEXACHLORO-l,3-CYCLO-PENTADIENE DIMER HRS 1276 NCI-C06428 PERCHLORODIHOMOCUBANE PERCHLOROPENTA-CYCLODECANE PERCHLOROPENTACYCLO-(5.2,1, o2. 5,o3.5,o5.8)DECANE... 

DECABROMOBIPHENYL ETHER see PAU500 DECABROMOBIPHENYL OXIDE see PAU500 DECABROMODIPHENYL see PCC480 DECABROMODIPHENYL OXIDE see PAU500 DECABROMOPHENYL ETHER see PAU500 DECACHLOROKETONE see KEAOOO DECACHLORO-l,3,4-METHENO-2H-CYCLOBUTA(cd)PENTALEN-2-ONE see KEAOOO DECACHLOROOCTAHYDROKEPONE-2-ONE see KEAOOO... 

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