dieldrin

Also known as (1aR,2R,2aS,3S,6R,6aR,7S,7aS)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphtho[2,3-b]oxirene, HEOD, (1aalpha,2beta,2aalpha,3beta,6beta,6aalpha,7beta,7aalpha)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphtho[2,3-b]oxirene, 1,2,3,4,10,10-hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-endo,exo-5,8-dimethanonaphthalene

Chemical data

Formula: C12H8Cl6O
Molecular weight: 380.9 g/mol
IUPAC name: (1R,2S,3S,6R,7R,8S,9S,11R)-3,4,5,6,13,13-hexachloro-10-oxapentacyclo[6.3.1.13,6.02,7.09,11]tridec-4-ene
SMILES: C1[C@@H]2[C@H]3[C@@H]([C@H]1[C@H]4[C@@H]2O4)[C@]5(C(=C([C@@]3(C5(Cl)Cl)Cl)Cl)Cl)Cl
InChIKey: DFBKLUNHFCTMDC-PICURKEMSA-N
XLogP: 3.7
Polar surface area: 12.5 Å²
H-bond donors: 0
H-bond acceptors: 1
Formal charge: 0

via PubChem

Research

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Contents

Production
Use
Metabolism
Legislation and history
Australia
References
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Dieldrin is an organochlorine compound originally produced in 1948 by J. Hyman & Co, Denver, as an insecticide. Dieldrin is closely related to aldrin, which reacts further to form dieldrin. Aldrin is not toxic to insects; it is oxidized in the insect to form dieldrin which is the active compound. Both dieldrin and aldrin are named after the Diels–Alder reaction which is used to form aldrin from a mixture of norbornadiene and hexachlorocyclopentadiene.

Originally developed in the 1940s as an alternative to DDT, dieldrin proved to be a highly effective insecticide and was very widely used during the 1950s to early 1970s. Endrin is a stereoisomer of dieldrin.