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Dieldrin information


Dieldrin
Names
IUPAC name
(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
Other names
Dieldrin, HEOD
Identifiers
CAS Number
  • 60-57-1 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:34696 checkY
ChEMBL
  • ChEMBL481118 ☒N
ChemSpider
  • 10292746 checkY
ECHA InfoCard 100.000.440 Edit this at Wikidata
KEGG
  • C13718 checkY
PubChem CID
  • 969491
UNII
  • I0246D2ZS0 checkY
CompTox Dashboard (EPA)
  • DTXSID9020453 Edit this at Wikidata
InChI
  • InChI=1S/C12H8Cl6O/c13-8-9(14)11(16)5-3-1-2(6-7(3)19-6)4(5)10(8,15)12(11,17)18/h2-7H,1H2/t2-,3+,4+,5-,6-,7+,10+,11- checkY
    Key: DFBKLUNHFCTMDC-PICURKEMSA-N checkY
  • InChI=1/C12H8Cl6O/c13-8-9(14)11(16)5-3-1-2(6-7(3)19-6)4(5)10(8,15)12(11,17)18/h2-7H,1H2/t2-,3+,4+,5-,6-,7+,10+,11-
    Key: DFBKLUNHFCTMDC-PICURKEMBL
SMILES
  • ClC5(Cl)[C@]3(Cl)C(\Cl)=C(\Cl)[C@@]5(Cl)[C@H]4[C@H]1C[C@H]([C@@H]2O[C@H]12)[C@@H]34
Properties
Chemical formula
C12H8Cl6O
Molar mass 380.91 g/mol
Appearance colorless to light tan crystals
Density 1.75 g/cm3
Melting point 176 to 177 °C (349 to 351 °F; 449 to 450 K)
Boiling point 385 °C (725 °F; 658 K)
Solubility in water
0.02%[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
potential carcinogen[1]
Flash point noncombustible[1]
Lethal dose or concentration (LD, LC):
LD50 (median dose)
45 mg/kg (oral, rabbit)
49 mg/kg (oral, guinea pig)
38 mg/kg (oral, mouse)
65 mg/kg (oral, dog)
38 mg/kg (oral, rat)[2]
LC50 (median concentration)
80 mg/m3 (cat, 4 hr)
13 mg/m3 (rat, 4 hr)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 0.25 mg/m3 [skin][1]
REL (Recommended)
Ca TWA 0.25 mg/m3 [skin][1]
IDLH (Immediate danger)
Ca [50 mg/m3][1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

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.

However, it is an extremely persistent organic pollutant; it does not easily break down. Furthermore, it tends to biomagnify as it is passed along the food chain.[3] Long-term exposure has proven toxic to a very wide range of animals including humans, far greater than to the original insect targets. People who on purpose or accidentally ate large amounts of aldrin or dieldrin have suffered convulsions (spasms), and some died. Workers who were exposed to lower amounts of these chemicals, but for a longer period of time, had headaches, dizziness, irritability, vomiting, and uncontrolled muscle movement.[4] For this reason, it is now banned in most of the world.

It has been linked to health problems such as Parkinson's, breast cancer, and immune, reproductive, and nervous system damage. It is also an endocrine disruptor, acting as an estrogen and antiandrogen, and can adversely affect testicular descent in the fetus if a pregnant woman is exposed to it.[5]

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0206". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b "Dieldrin". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Cite error: The named reference Jorgensen2001 was invoked but never defined (see the help page).
  4. ^ "Aldrin/Dieldrin | ToxFAQs™ | ATSDR". wwwn.cdc.gov. Retrieved 2023-03-02.
  5. ^ Andersen HR, Vinggaard AM, Rasmussen TH, Gjermandsen IM, Bonefeld-Jørgensen EC (February 2002). "Effects of currently used pesticides in assays for estrogenicity, androgenicity, and aromatase activity in vitro". Toxicology and Applied Pharmacology. 179 (1): 1–12. doi:10.1006/taap.2001.9347. PMID 11884232.

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Dieldrin

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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,...

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Aldrin

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into the environment. Though it is rapidly converted to dieldrin by plants and bacteria, dieldrin maintains the same toxic effects and slow decay of aldrin...

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Persistent organic pollutant

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POPs identified by the Stockholm Convention include aldrin, chlordane, dieldrin, endrin, heptachlor, HCB, mirex, toxaphene, PCBs, DDT, dioxins, and polychlorinated...

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IARC group 2A

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4'-Dichlorodiphenyltrichloroethane (DDT) Diethyl sulfate Dieldrin, and aldrin metabolized to dieldrin Dimethylcarbamoyl chloride Dimethylformamide 1,2-Dimethylhydrazine...

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Tineola bisselliella

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pentachlorophenol or BHC at 0.5%, DDT at 0.2%, chlordecone and mirex at 0.06%, and dieldrin at 0.05%. Imidazole (a non-chlorinated aromatic heterocyclic) at 1% also...

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Insecticide

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persistent organic pollutants. These include: aldrin, chlordane, DDT, dieldrin, endrin, heptachlor, mirex and toxaphene.[citation needed] Solid bait and...

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Pest control

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Chlordane Cyclodiene 1,2-DCB 1,4-DCB 1,1-DCE 1,2-DCE DDD DDE DDT DFDT Dicofol Dieldrin Endosulfan Endrin Heptachlor Kepone Lindane Methoxychlor Mirex Tetradifon...

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Silent Spring

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some research had been done to determine the effects of heptachlor and dieldrin on wild and domestic animals and to find the minimum amount that would...

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Drin

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a group of chlorinated insecticides whose names end in "-drin": Aldrin Dieldrin Endrin This disambiguation page lists articles about distinct geographical...

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Endrin

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is the final step in synthesizing endrin. Endrin is a stereoisomer of dieldrin with comparable properties, though endrin degrades more easily. Endrin...

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Quercetin

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(cis-hinokiresinol)) Metalloestrogens (e.g., cadmium) Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan)...

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Locust

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rollers and other mechanical methods. By the 1950s, the organochloride dieldrin was found to be an extremely effective insecticide, but it was later banned...

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Chlordane

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organochlorine insecticides are aldrin and its epoxide, dieldrin, as well as endrin, which is a stereoisomer of dieldrin. Cyclodiene derives its name from hexachlorocyclopentadiene...

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Organochlorine chemistry

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after a single stimulus.: 255  Chlorinated cyclodienes include aldrin, dieldrin, endrin, heptachlor, chlordane and endosulfan. A 2- to 8-hour exposure...

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Glossary of entomology terms

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solvents in some formulations may damage certain crops. cf. the related Dieldrin, Endrin, Isodrin algophagy Feeding on algae. alitrunk Name given to the...

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Tarpon

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1989. Wade, Richard Archer. "Ecology of Juvenile Tarpon and Effects of Dieldrin on Two Associated Species." Bureau of Sport Fisheries and Wildlife. 1969...

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Phenibut

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Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil)...

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Permethrin

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Chlordane Cyclodiene 1,2-DCB 1,4-DCB 1,1-DCE 1,2-DCE DDD DDE DDT DFDT Dicofol Dieldrin Endosulfan Endrin Heptachlor Kepone Lindane Methoxychlor Mirex Tetradifon...

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Glutamine

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Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil)...

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Baclofen

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Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil)...

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Brown pelican

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States Endangered Species Act from 1970 to 2009, as pesticides such as dieldrin and DDT threatened its future in the Southeastern United States and California...

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Trenbolone acetate

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Cioteronel Cyanonilutamide Darolutamide DDT (via metabolite p,p’-DDE) Dieldrin DIMP Endosulfan Enzalutamide EPI-001 Fenarimol Flutamide Hydroxyflutamide...

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Penicillin

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Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil)...

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List of insecticides

Last Update:

dicloromezotiaz [Wikidata] dicresyl dicrotophos dicyclanil [Wikidata] dieldrin diflubenzuron dimefluthrin [Wikidata] dimefox dimetan [Wikidata] dimethacarb...

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Dihydrotestosterone

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Cioteronel Cyanonilutamide Darolutamide DDT (via metabolite p,p’-DDE) Dieldrin DIMP Endosulfan Enzalutamide EPI-001 Fenarimol Flutamide Hydroxyflutamide...

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Testosterone

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Cioteronel Cyanonilutamide Darolutamide DDT (via metabolite p,p’-DDE) Dieldrin DIMP Endosulfan Enzalutamide EPI-001 Fenarimol Flutamide Hydroxyflutamide...

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Valproate

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Cioteronel Cyanonilutamide Darolutamide DDT (via metabolite p,p’-DDE) Dieldrin DIMP Endosulfan Enzalutamide EPI-001 Fenarimol Flutamide Hydroxyflutamide...

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Trenbolone

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Cioteronel Cyanonilutamide Darolutamide DDT (via metabolite p,p’-DDE) Dieldrin DIMP Endosulfan Enzalutamide EPI-001 Fenarimol Flutamide Hydroxyflutamide...

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