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| verifiedrevid = 443723455 |
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| verifiedrevid = 443833173 |
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| Name = Endrin |
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| ImageFile = Endrin.svg |
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| Name = Endrin |
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| ImageFile1 = Endrin.svg |
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<!-- | ImageSize = 200px --> |
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| ImageName1 = |
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| ImageFile2 = Endrin-3D-balls.png |
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| IUPACName = Mendrin, Compound 269 |
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''(1a''R'',2''S'',2a''S'',3''S'',6''R'',6a''R'',7''R'',7a''S'')-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphthooxirene |
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| PIN = (1a''R'',2''R'',2a''R'',3''R'',6''S'',6a''S'',7''S'',7a''S'')-3,4,5,6,9,9-Hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphthooxirene |
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| OtherNames = Mendrin, Compound 269, 1,2,3,4,10,10-Hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-endo,endo-5,8-dimethanonaphthalene |
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| Other names = Mendrin''', and '''Compound 269'' |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 21782117 |
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| ChemSpiderID = 21782117 |
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| 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+ |
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| 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+ |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C18124 |
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| KEGG = C18124 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = OB9NVE7YCL |
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| UNII = OB9NVE7YCL |
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| PubChem = 3048 |
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| ChEBI = 81526 |
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| ChEMBL = 44072 |
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| EC_number = 200-775-7 |
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| RTECS = IO1575000 |
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| UNNumber = 2761 |
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| SMILES = C1C2C3C(C1C4C2O4)C5(C(=C(C3(C5(Cl)Cl)Cl)Cl)Cl)Cl |
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| SMILES = C1C2C3C(C1C4C2O4)C5(C(=C(C3(C5(Cl)Cl)Cl)Cl)Cl)Cl |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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|C=12|H=8|Cl=6|O=1 |
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| C=12 | H=8 | Cl=6 | O=1 |
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| MolarMass = 380.907 g/mol |
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| MolarMass = 380.907 g/mol |
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| Appearance = Colorless to tan crystalline solid |
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| Density = |
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| Density = 1.77 g/cm{{sup|3}} <ref name = CES/> |
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| MeltingPt = 200 °C (decomposes) |
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| Solubility = 0.23 mg/L<ref name = PDS>{{cite web|title = Endrin (PDS)|publisher = IPCS|url = http://www.inchem.org/documents/pds/pds/pest1_e.htm|access-date = 13 March 2015|archive-url = https://web.archive.org/web/20140702023553/http://inchem.org/documents/pds/pds/pest1_e.htm|archive-date = 2 July 2014|url-status = dead}}</ref> |
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| MeltingPtC = 200 |
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| MeltingPt_notes = (decomposes) |
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| VaporPressure = 2.6 x 10{{sup|-5}} Pa<ref name = CES>{{cite web|title = Endrin|publisher = Deutsche Gesellschaft für Technische Zusammenarbeit|url = http://ces.iisc.ernet.in/energy/HC270799/HDL/ENV/enven/vol338.htm|access-date = 13 March 2015}}</ref> |
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|Section3={{Chembox Hazards |
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| NFPA-H = 3 |
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| NFPA-F = 0 |
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| NFPA-R = 0 |
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| PEL = TWA 0.1 mg/m<sup>3</sup> <ref name=niosh>{{PGCH|0252}}</ref> |
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| IDLH = 2 mg/m<sup>3</sup><ref name=niosh/> |
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| REL = TWA 0.1 mg/m<sup>3</sup> <ref name=niosh/> |
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| LD50 = 3 mg/kg (oral, monkey)<br/>16 mg/kg (oral, guinea pig)<br/>10 mg/kg (oral, hamster)<br/>3 mg/kg (oral, rat)<br/>7 mg/kg (oral, rabbit)<br/>1.4 mg/kg (oral, mouse)<ref name=IDLH>{{cite web |url = https://www.cdc.gov/niosh/idlh/72208.html |title = Endrin |work = Immediately Dangerous to Life or Health Concentrations (IDLH) |publisher = National Institute for Occupational Safety and Health (NIOSH) |date = 4 December 2014 |access-date = 19 March 2015}}</ref> |
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| LDLo = 5 mg/kg (cat, oral)<ref name=IDLH/> |
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| FlashPt = noncombustible |
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| FlashPt_ref =<ref name=niosh/> |
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| GHSPictograms = {{GHS06}}{{GHS08}}{{GHS09}} |
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| GHSSignalWord = Danger |
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| MainHazards = Toxic with delayed onset of toxicity |
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| HPhrases = {{H-phrases|301|310|351|372|410}} |
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| PPhrases = {{P-phrases|201|202|260|262|264|270|273|280|281|301+310|302+350|308+313|310|314|321|322|330|361|363|391|405|501}} |
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'''Endrin''' is an ] that was primarily used as an ]. It is a colourless odorless solid, although commercial samples are often off-white. It is also a ]. This compound became infamous as ] and for this reason is banned in many countries.<ref name=prn>"Poison Control: Dangers of 'persistent organic pollutants' in the environment." </ref><ref name=Ullmann>Robert L. Metcalf “Insect Control” in Ullmann’s Encyclopedia of Industrial Chemistry” Wiley-VCH, Weinheim, 2002. {{DOI|10.1002/14356007.a14_263}}</ref> |
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'''Endrin''' is an ] with the ] C<sub>12</sub>H<sub>8</sub>Cl<sub>6</sub>O that was first produced in 1950 by ] and ]. It was primarily used as an ], as well as a ] and ]. It is a colourless, odorless solid, although commercial samples are often off-white. Endrin was manufactured as an emulsifiable solution known commercially as Endrex.<ref name=":1" /> The compound became infamous as a ] and for this reason it is banned in many countries.<ref name=":3">{{Cite web|url = http://www.environment.gov.au/protection/chemicals-management/pops|title = Stockholm Convention on Persistent Organic Pollutants (POPs)|date = 2013|access-date = 30 March 2015|publisher = Commonwealth of Australia: Department of the Environment}}</ref> |
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In the environment endrin exists as either endrin aldehyde or endrin ketone and can be found mainly in bottom sediments of bodies of water.<ref name=":0" /><ref name=":5">{{Cite news|url = http://permanent.access.gpo.gov/LPS45098/endrin.pdf|title = Procedures for the Derivation of Equilibrium Partitioning Sediment Benchmarks (ESBs) for the Protection of Benthic Organisms: Endrin|last = Berry|first = Walter|date = August 2003|work = EPA: Office of Research and Development}}</ref> Exposure to endrin can occur by inhalation, ingestion of substances containing the compound, or skin contact.<ref name=":0">{{Cite web|url = http://www.atsdr.cdc.gov/ToxProfiles/tp89.pdf|title = Toxicological Profile for Endrin|date = August 1996|access-date = 30 March 2015|website = Agency for Toxic Substances and Disease Registry|publisher = United States Department of Health and Human Services}}</ref> Upon entering the body, it can be stored in body fats and can act as a ] on the ], which can cause convulsions, seizures, or even death.<ref name=":6">{{Cite web|url = http://www.faa.gov/data_research/research/med_humanfacs/oamtechreports/1970s/media/AM70-11.pdf|title = Some Acute and Chronic Effects of Endrin on the Brain|date = July 1970|access-date = 14 March 2015|publisher = Federal Aviation Administration: Office of Aviation Medicine}}</ref> |
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==Production and uses== |
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Endrin is produced via a multistep route from ].<ref name=Ullmann/> Diels-Alder addition of acetylene gives an isomer of ]. This compound undergoes a second Diels-Alder addition, this time with ]. The resulting polycyclic derivative is ] to give endrin. Endrin is a ] of ]. |
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Although endrin is not currently classified as a ],<ref name=":1" /> nor as a human ], it is still a toxic chemical in other ways with detrimental effects.<ref>{{Cite web|url = http://www.epa.gov/iris/subst/0363.htm|title = Endrin (CASRN 72-20-8)|date = September 1988|access-date = 30 March 2015|website = Integrated Risk Information System|publisher = United States Environmental Protection Agency}}</ref> Due to these toxic effects, the manufacturers cancelled all use of endrin in the United States by 1991. Food import concerns have been raised because some countries may have still been using endrin as a pesticide.<ref name=":0" /> |
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The majority of endrin (about 80%) was consumed as a spray to control insect pests of cotton. It was also used on rice, to some extent on ], in a limited way on ] crops and ]s, and in Australia on ] and ]. It was occasionally used in ]s as a control of ]s, where it is sprayed on the ground under the trees in autumn or spring, often as a solution in mineral oil. As a seed treatment, it was used for cotton seed in the United States, and for beans seeds in Australia. |
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==History== |
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==Environmental problems== |
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J. Hyman & Company first developed endrin in 1950. ] was licensed in the United States and in the Netherlands to produce it. ] was the other producer in the Netherlands. Endrin was used globally until the early 1970s. Due to its toxicity, it was banned or severely restricted in many countries. In 1982, Shell discontinued its manufacturing.<ref name=":1">{{Cite web|url = http://www.inchem.org/documents/ehc/ehc/ehc130.htm|title = Environmental Health Criteria 130: Endrin|date = 1992|access-date = 30 March 2015|website = International Programme on Chemical Safety|publisher = World Health Organization|last1 = van Esch|first1 = G. T.|last2 = van Heemstra-Lequin|first2 = E. A. H.}}</ref> |
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The use of endrin is ] in many countries. Like related organochlorine pesticides, it is ]. Thus, it tends to ] in fatty tissues of organisms living in water. Some estimates indicate its ] in ] is over 10 years. In comparison with dieldrin, endrin is less persistent in the environment. |
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In 1962, an estimated 2.3-4.5 million kilograms of endrin were sold by Shell in the USA. In 1970, Japan imported 72,000 kilograms of endrin. From 1963 until 1972, Bali used 171 to 10,700 kilograms of endrin annually for the production of ] until endrin use was discontinued in 1972.<ref name=":1" /> Taiwan reported to show higher levels of ] including endrin in soil samples of paddy fields, compared to other Asian countries such as Thailand and Vietnam. During the 1950s-1970s over two million kilograms of organochlorine pesticides were estimated of having been be released into the environment per year. Endrin was banned in the United States on October 10, 1984.<ref name=":5" /> Taiwan banned endrin's use as a pesticide in 1971 and regulated it as a toxic chemical in 1989.<ref name=Taiwan>{{cite journal|last1=Tsai|first1=Wen-Tien|title=Current Status and Regulatory Aspects of Pesticides Considered to be Persistent Organic Pollutants (POPs) in Taiwan|journal=International Journal of Environmental Research and Public Health|date=12 October 2010|volume=7|issue=10|pages=3615–3627|doi=10.3390/ijerph7103615|pmid=21139852|pmc=2996183|doi-access=free}}</ref> |
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==Safety== |
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Endrin is toxic with an {{LD50}} is 17.8 and 7.5 mg/kg (oral, rat). Acute endrin poisoning in humans affects primarily the ]. Food contaminated with endrin caused several clusters of poisonings worldwide, especially affecting children.<ref name=prn/> Orally ingested endrin is eliminated mostly in ].<ref>WHO report: 1970 Evaluations of some pesticide residues in food. </ref> It is very toxic to aquatic organisms, namely ], aquatic ]s, and ]. The U.S. EPA has set a freshwater acute criterion of 0.086ug/L and a chronic criterion of 0.036ug/L. In saltwater, the numbers are acute 0.037 and chronic 0.0023ug/L. <ref> US EPA Criteria for Aquatic Life (pdf) </ref> Human health contaminate criterion for water plus organism is 0.059ug/L. <ref> US EPA human health criteria document</ref> Drinking water limits (maximum contaminant level (mcl)) is set to 2 ppb. <ref>US EPA Drinking water document</ref> |
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In May 2004, the ] came into effect and listed endrin as one of the 12 initial ] (POPs) that have been causing adverse effects on humans and the environment. The convention requires the participating parties to take measures to eliminate or restrict the production of POPs.<ref name=":4">{{cite web|title=History of the negotiations of the Stockholm Convention|url=http://chm.pops.int/TheConvention/Overview/History/Overview/tabid/3549/Default.aspx|website=Stockholm Convention|access-date=20 March 2015}}</ref> |
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==References== |
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<references/> |
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==Production== |
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The synthesis of endrin begins with the condensation of ] with ]. The product is then ]. Following reaction with ], ] is formed. ] formation by adding either ] or ] to the isodrin is the final step in synthesizing endrin.<ref name=":1" /> |
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Endrin is a ] of ]<ref name=":7">{{Cite web|url = https://www.cdc.gov/biomonitoring/Endrin_BiomonitoringSummary.html|title = Organochlorine Pesticides Overview: Endrin|date = December 2013|access-date = 30 March 2015|website = CDC - National Biomonitoring Program|publisher = Center for Disease Control and Prevention}}</ref> with comparable properties, though endrin degrades more easily.<ref name=":5" /> |
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==Use== |
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Endrin was formulated as emulsifiable concentrates (ECs), ], granules, field strength dusts (FSDs), and pastes. The product could then be ] or by handheld sprayers in its various formulations.<ref name=":2">{{Cite web|url = http://www.inchem.org/documents/hsg/hsg/hsg060.htm|title = Endrin: Health and Safety Guide No. 60|date = 1991|access-date = 30 March 2015|website = International Programme on Chemical Health|publisher = World Health Organization}}</ref> |
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Endrin has been used primarily as an agricultural ] on tobacco, apple trees, cotton, sugar cane, rice, cereal, and grains.<ref>{{Cite web|url = http://water.epa.gov/drink/contaminants/basicinformation/endrin.cfm|title = Basic Information about Endrin in Drinking Water|date = February 9, 2014|access-date = 30 March 2015|publisher = United States Environmental Protection Agency}}</ref> It is effective against a variety of species, including ], ]s, cut worms and ].<ref>{{Cite web|url = http://www.inchem.org/documents/pds/pds/pest1_e.htm|title = Data Sheets on Pesticides No. 1: Endrin|date = January 1975|access-date = 30 March 2015|website = International Programme on Chemical Safety|publisher = World Health Organization; Food and Agriculture Organization|archive-url = https://web.archive.org/web/20140702023553/http://inchem.org/documents/pds/pds/pest1_e.htm|archive-date = 2 July 2014|url-status = dead}}</ref> In addition, endrin has been employed as a rodenticide and ].<ref name=":0" /> In Malaysia, fish farms used a solution of endrin as a ] to rid mine pools and fish ponds of all fish prior to restocking.<ref name="USGS">{{Cite web|url = http://www.umesc.usgs.gov/documents/reports/2003/bor_final_report.pdf|title = Integrated Management Techniques to Control Nonnative Fishes|date = December 2003|access-date = 30 March 2015|website = Upper Midwest Environmental Sciences Center|publisher = United States Geological Survey}}</ref> |
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A study conducted from 1981 to 1983 in the US aimed to determine endrin's effects on non-target organisms when applied as a ] in orchards. Most wildlife in and around the orchard was found to have endrin exposure, with endrin toxicity accounting for more than 24% of bird deaths recorded.<ref>{{cite journal|last1=Blus|first1=L.J.|last2=Henny| first2=C.J.|last3=Grove|first3=R.A.|title=Rise and fall of endrin usage in Washington State fruit orchards: Effects on wildlife|journal=Environmental Pollution|date=January 1989|volume=60|issue=3–4|pages=331–349|doi=10.1016/0269-7491(89)90113-9|pmid=15092385|url=https://pubs.er.usgs.gov/publication/1015819}}</ref> Endrin was eventually banned in the US on October 10, 1984.<ref name=":5" /> |
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== Health effects == |
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=== Exposure and metabolism === |
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Exposure to endrin can occur by inhalation, ingestion of substances containing the compound, or by skin contact. In addition to inhalation and skin contact, infants can be exposed by ingesting the ] of an exposed woman. '']'', fetuses are exposed by way of the ] if the mother has been exposed.<ref name=":7" /><ref>{{Cite web|url = http://www.nrdc.org/breastmilk/diel.asp|title = Healthy Milk, Healthy Baby - Chemical Pollution and a Mother's Milk|date = 25 March 2005|access-date = 30 March 2015|publisher = National Resources Defense Council|archive-date = 4 December 2006|archive-url = https://web.archive.org/web/20061204231854/http://www.nrdc.org///breastmilk/diel.asp|url-status = dead}}</ref> |
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Upon entering the body, endrin metabolizes into ''anti''-12-hydroxyendrin and other metabolites, which can be expelled in the urine and feces. Both ''anti''-12-hydroxyendrin and its metabolite, 12-ketoendrin, are likely responsible for the toxicity of endrin.<ref name=":0" /> The rapid metabolism of endrin into these metabolites makes detection of endrin itself difficult unless exposure is very high.<ref name=":7" /> |
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=== Neurological effects === |
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Symptoms of endrin poisoning include headache, dizziness, nervousness, confusion, nausea, vomiting, and convulsions.<ref name=":0" /> Acute endrin poisoning in humans affects primarily the ]. There, it can act as a ] that blocks the activity of inhibitory ]s.<ref name=":7" /> In cases of acute exposure, this may result in seizures, or even death. Because endrin can be stored in body fats, acute endrin poisoning can lead to recurrent seizures when ]s induce the release of endrin back into the body, even months after the initial exposure is terminated.<ref name=":6" /> |
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People occupationally exposed to endrin may experience abnormal ] readings even if they exhibit none of the clinical symptoms, possibly due to injury to the ]. These readings show ] synchronous ] with synchronous ] complexes. EEG readings can take up to one month to return to normal.<ref name=":0" /> |
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=== Developmental effects === |
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Though endrin exposure has not been found to adversely affect ] in mammals, an increase in fetal mortality has been observed in mice, rats, and mallard ducks. In those animals that have survived gestation, developmental abnormalities have been observed, particularly in rodents whose mothers were exposed to endrin early in pregnancy. In hamsters, the number of cases of fused ribs, ], open eyes, webbed feet, and ] have increased. Along with open eyes and cleft palate, mice have developed with fused ribs and ].<ref name=":0" /> Skeletal abnormalities in rodents have also been reported.<ref name=":7" /> |
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<big>'''Effects on animals'''</big> |
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Animals that ate or breathed high levels of Endrin had very similar effects to those seen in humans, with the nervous system being the same target in both animals and humans. When Endrin attacks the nervous system in typically causes convulsions in the animals. Endrin exposure also lead liver damage in all the animals studied. Endrin is highly toxic for all animal species however, fish and other aquatic organisms seemed to be effected the most. <ref>{{Cite web |date= |title=Endrin - ToxicFAQs |url=https://www.atsdr.cdc.gov/toxfaqs/tfacts89.pdf }}</ref> |
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=== Other effects === |
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Higher doses of endrin have been found to cause the following in rodents: ]; inflammation of the liver, ], and liver ]; possible kidney degradation;<ref name=":7" /> and a decrease in body weight and body weight gain.<ref name=":0" /> |
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Endrin is very toxic to aquatic organisms, namely ], aquatic ]s, and ].<ref name="epa1980">{{Cite web|url = http://water.epa.gov/scitech/swguidance/standards/criteria/upload/2001_10_12_criteria_ambientwqc_endrin80.pdf| title = Ambient Water Quality Criteria for Endrin|date = October 1980|access-date = 30 March 2015|website = EPA Water|publisher = United States Environmental Protection Agency}}</ref> It was found to ] of infected fish for up to one month.<ref name="USGS" /> |
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=== Monitoring Methods Used by OSHA === |
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Analyte code (IMIS no.): 1017 |
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Sampler/Sampling media: 0.8 μm Cellulose ester membrane + Chromosorb 102, (100/50 mg) |
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Sampling volume (TWA)*: 12-400 L |
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Sampling flow rate (TWA)*: 0.5-1 L/min |
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Analytical method instruments: GC-ECD<ref>{{Cite web |date=29 January 2021 |title=Occupational Safety and Health Administration |url=https://www.osha.gov/chemicaldata/493 |access-date=14 March 2024 |website=OSHA Occupational Chemical Database}}</ref> |
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=== 1984 poisoning outbreak in Pakistan === |
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From July 14 to September 26, 1984, an outbreak of endrin poisoning occurred in 21 villages in and around ], a subdistrict of the ] of ]. Eighty percent of the 194 known cases were children under the age of 15. Poisoned individuals had ] along with ], ], and ], leaving 19 people dead. Some individuals had low grade ] (37.8 °C/100 °F, ]) following seizures. The more seriously affected had less vomiting, but higher temperatures than people who were less affected. Most patients could be controlled in under two hours using ], ], and ], though the more seriously affected patients required ]. Recovery took up to two days. Following treatment, patients reported not remembering their seizures. The outbreak affected both men and women equally.<ref name=":8">{{Cite web|url = https://www.cdc.gov/mmwr/preview/mmwrhtml/00000450.htm#content_area|title = International Notes Acute Convulsions Associated with Endrin Poisoning -- Pakistan|date = 14 December 1984|access-date = 30 March 2015|website = Morbidity and Mortality Weekly Report (MMWR)|publisher = Center for Disease Control}}</ref> |
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Based on the demographics of the affected individuals and their area of residence, the outbreak was likely caused by endrin contamination of food.<ref>{{Cite journal|url = http://www.jpma.org.pk/PdfDownload/5149.pdf|date = October 1992|access-date = 30 March 2015|journal = Jpma. The Journal of the Pakistan Medical Association|last = Jabbar|first = Abdul|title = Pesticide poisoning in humans|volume = 42|issue = 10|pages = 251–255|pmid = 1469773}}</ref> As members of these villages rarely had contact with one another, investigators determined that contaminated sugar shipped to the villages was the most probable cause, though no credible evidence was found to support this. Around this time, endrin was being used by cotton and sugar cane farmers in the Punjab region. A number of truck drivers stated that they had used the same trucks to deliver endrin to farmers and to pick up crops for Talagang, possibly leading to contamination.<ref name=":8" /> |
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== Environmental behavior == |
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Insecticides like dieldrin and endrin have been shown to persist for decades in the environment.<ref name=Bioremediation>{{cite journal|last1=Matsumoto|first1=Emiko|last2=Kawanaka|first2=Youhei|last3=Yun|first3=Sun-Ja|last4=Oyaizu|first4=Hiroshi|title=Bioremediation of the organochlorine pesticides, dieldrin and endrin, and their occurrence in the environment|journal=Applied Microbiology and Biotechnology|date=4 July 2009|volume=84|issue=2|pages=205–216|doi=10.1007/s00253-009-2094-5|pmid=19578846|s2cid=10299302}}</ref> A definitive detection of the residues was not possible until 1971 when ] started being used as a detector in ].<ref name="Chlorinated Psticides">{{cite book|last1=Zitko|first1=Vladimir|title=Persistent Organic Pollutants|date=2003|publisher=Springer-Verlag|location=Berlin Heidelberg|isbn=978-3-540-43728-4|pages=47–90|url=http://www.lu.lv/ecotox/publikacijas/POP.PDF|access-date=25 March 2015|archive-url=https://web.archive.org/web/20150402164556/http://www.lu.lv/ecotox/publikacijas/POP.PDF|archive-date=2 April 2015|url-status=dead}}</ref> Detection of these chemicals in the environment has been reported across the world up to 2005,<ref name=Bioremediation /> even though the frequency of reported cases are low due to its relatively small-scale use and very low concentrations.<ref name="Chlorinated Psticides" /> |
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Endrin regularly enters the environment when applied to crops or when rain washes it off. It has been found in water, sediments, atmospheric air and biotic environment, even after uses have been stopped.<ref name=Bioaccumulation>{{cite journal|last1=Chopra|first1=A. K.|last2=Sharma|first2=Mukesh Kumar|last3=Chamoli|first3=Shikha|title=Bioaccumulation of organochlorine pesticides in aquatic system—an overview|journal=Environmental Monitoring and Assessment|date=February 2011|volume=173|issue=1–4|pages=905–916|doi=10.1007/s10661-010-1433-4|pmid=20306340|s2cid=25854160}}</ref> ] strongly resist degradation, are poorly soluble in water but highly soluble in lipids, which is called ].<ref name="Chlorinated Psticides" /> This leads to ] in fatty tissues of organisms, mainly those dwelling in water. A high ] of 1335–10,000 has been reported in fish.<ref name=Factsheet>{{cite web|title=Technical Factsheet on: Endrin|url=http://www.epa.gov/ogwdw/pdfs/factsheets/soc/tech/endrin.pdf|website=www.epa.gov|publisher=United States Environmental Protection Agency|access-date=26 March 2015}}</ref> Endrin binds very strongly to ] in soil and aquatic sediments due to their high ] coefficient,<ref name="Chlorinated Psticides" /> making it less likely to leach into groundwater, even though contaminated groundwater samples have been found. In 2009, ] released data indicating that the endrin in soil could last up to 14 years or more.<ref name="Factsheet" /> The extent of endrin's persistence depends highly on local conditions. For example, high temperature (230 °C) or intense sunlight leads to more rapid breakdown of endrin into endrin ketone and endrin aldehyde, however, this breakdown is less than 5%.<ref name=":0" /> |
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=== Removal from the environment === |
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In the United States, endrin was mainly disposed in land until U.S. federal regulations were applied in 1987 on land disposal of wastes containing endrin.<ref name=:0 /> Primary methods of endrin disappearance from soil are ] and ].<ref name=IPCS>{{cite book|last1=Esch|first1=G. T. van|last2=Heemstra-Lequin|first2=E. A. H. van|title=Endrin|date=1992|publisher=World Health Organization|location=Geneva|isbn=92-4-157130-6|pages=1–234|url=http://whqlibdoc.who.int/ehc/WHO_EHC_130_eng.pdf|access-date=29 March 2015}}</ref> Under ], endrin forms δ-ketoendrin and ] (IPCS) claims that in intense summer sun, about 50% of endrin is isomerized to δ-ketoendrin in 7 days.<ref name=IPCS /> In ] conditions microbial degradation by fungi and bacteria takes place to form the same major end product.<ref name=":2" /> |
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Mammalian metabolic studies with endrin are difficult because of the high toxicity of the compound. Baldwin M K identified two hydroxylated metabolites in the faeces of rats fed a diet containing 4 parts per million of endrin.<ref>{{Cite journal |last1=Baldwin |first1=Michael K. |last2=Robinson |first2=John. |last3=Parke |first3=Dennis V. |date=1970 |title=Metabolism of endrin in the rat |journal=Journal of Agricultural and Food Chemistry |volume=18 |issue=6 |pages=1117–1123 |doi=10.1021/jf60172a020|pmid=5483050 }}</ref> At least one was the result of hydroxylation of the methylene bridge. The other might be the opposite isomer, or it could conceivably be the result of hydroxylation at another site. Endrin rarely occurs as a resdue in tissues. What is found is the ketone, probably produced by metabolism of the alcohol derived from the methylene group. |
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] (HSDB) lists ] and ] for field disposal of small quantities of endrin. In reductive dechlorination, endrin's ] atoms were completely replaced with ] atoms, which is suspected to be more environmentally acceptable.<ref>{{cite journal|last1=Butler|first1=L. C.|last2=Staiff|first2=D. C.|last3=Sovocool|first3=G. W.|last4=Wilson|first4=N. K.|last5=Magnuson|first5=J. A.|title=Reductive degradation of dieldrin and endrin in the field using acidified zinc|journal=Journal of Environmental Science and Health|date=1981|volume=16|issue=4|pages=395–408|doi=10.1080/03601238109372266|pmid=7288091|bibcode=1981JESHB..16..395B }}<!--|access-date=29 March 2015--></ref> Even though endrin binds very strongly to soil, ] has been proposed by group of Japanese scientists using crops in the family ]. {{as of| 2009}}, exact mechanisms behind the plant uptake of endrin have not been understood. Research in uptake mechanisms and factors that influence the uptake is needed for practical application.<ref name=Bioremediation /><nowiki/> |
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==Regulation== |
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=== United States === |
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In the United States, endrin has been regulated by the ]. It set a freshwater acute criterion of 0.086 μg/L and a chronic criterion of 0.036 μg/L. In saltwater, the numbers are acute 0.037 and chronic 0.0023 μg/L.<ref name=epa1980/> |
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The human health contaminate criterion for water plus organism is 0.059 μg/L.<ref name=epa2003>{{Cite web|url = http://water.epa.gov/scitech/swguidance/standards/criteria/health/15table-fs.cfm|title = Human Health Criteria|date = December 2003|access-date = 30 March 2015|website = EPA Water|publisher = United States Environmental Protection Agency}}</ref> |
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The drinking water limit (]) is set to 2 ppb.<ref name=epa2009>{{Cite web|url = http://water.epa.gov/drink/contaminants/index.cfm#two|title = Drinking Water Contaminants: National Primary Drinking Water Regulations|date = May 2009|access-date = 30 March 2015|website = EPA Water|publisher = United States Environmental Protection Agency}}</ref> |
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Use of endrin in ] has been advised against due to the zero tolerance of endrin levels in food products.<ref name ="USGS"/> |
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For occupational exposures to endrin, ] and ] have set ] at 0.1 mg/m<sup>3</sup>.<ref name=niosh/> |
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===International organizations=== |
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The ] lists Endrin as an obsolete pesticide in its 'Classification of Pesticides by Hazard' and did not assign any hazard class per the ].<ref>{{cite book|title=Classification of Pesticides by Hazard|url=https://www.who.int/ipcs/publications/pesticides_hazard/en/|archive-url=https://web.archive.org/web/20040708001948/http://www.who.int/ipcs/publications/pesticides_hazard/en/|url-status=dead|archive-date=July 8, 2004|publisher=WHO|access-date=30 March 2015|pages=81|isbn=978-92-4-154796-3|date=2010}}</ref> |
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=== Taiwan=== |
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Taiwan is not a party to the ] as of 2015, but has drafted its own "National Implementation Plan of the Stockholm Convention on Persistent Organic Pollutants" which was approved by the ] in April 2008.<ref name=Taiwan /> The Central Competent Authorities of Taiwan sets the limit of 20 mg/kg for soil pollution control. For marine environment quality, standards of 0.002 mg/L has been set. For occupational exposures to endrin, warning has been given that the contact with skin, eyes, and mucous membranes can contribute to the overall exposure.<ref name=Taiwan /> |
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==See also== |
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==See also== |
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* ] |
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==References== |
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{{reflist|30em}} |
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==External links== |
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* ChemSub Online, retrieved 9 April 2015 |
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