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Chemical compound From Wikipedia, the free encyclopedia

Group project: Endrin
Group members include DeusetScientia and Tracklete14
This sandbox will be used as a draft article for the topic

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Quick facts Names, Identifiers ...
Endrin
Names
IUPAC name
(1R,2S,3R,6S,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
Other names
Mendrin, Compound 269, (1aR,2S,2aS,3S,6R,6aR,7R,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, 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
Identifiers
3D model (JSmol)
ChemSpider
KEGG
UNII
  • 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-RVVFZPGKSA-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-RVVFZPGKBH
  • C1C2C3C(C1C4C2O4)C5(C(=C(C3(C5(Cl)Cl)Cl)Cl)Cl)Cl
Properties
C12H8Cl6O
Molar mass 380.907 g/mol
Appearance Colorless to tan crystalline solid
Density 1.77 g/cm3 [1]
Melting point 200 °C (392 °F; 473 K)
0.23 mg/L[2]
Vapor pressure 2.6 x 10-5 Pa[1]
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Flash point noncombustible [3]
Lethal dose or concentration (LD, LC):
3 mg/kg (oral, monkey)
16 mg/kg (oral, guinea pig)
10 mg/kg (oral, hamster)
3 mg/kg (oral, rat)
7 mg/kg (oral, rabbit)
1.4 mg/kg (oral, mouse)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.1 mg/m3 [skin][3]
REL (Recommended)
 TWA 0.1 mg/m3 [skin][3]
IDLH (Immediate danger)
 2 mg/m3[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Close

Endrin is an organochloride with the chemical formula C12H8Cl6O that was primarily used as an insecticide, as well as a rodenticide. It is a colourless odorless solid, although commercial samples are often off-white. Endrin was also sold as an emulsifiable solution known commercially as Shell Endrix. The compound endrin became infamous as a persistent organic pollutant and for this reason it is banned in many countries. [5]

Endrin can be found in our environment mainly in bottom sediments of bodies of water. [6] It is found in the environment as either endrin, endrin aldehyde or endrin ketone. Exposure to endrin can occur via inhalation, ingestion of substances containing endrin or skin contact. [7] Upon entering the bodies of animals and humans, it can be stored in body fats and acts as a neurotoxin on the central nervous system. It can cause convulsions and seizures or even death.[8]

Although endrin is not current classified as a human carcinogen, it is still a toxic chemical. [9] All use of endrin in the United states has been canceled by 1991. Food import restrictions were also put in place for the likelihood that some coutnries may have still been using endrin as a pesticide agent at that time. [7]

Production and Application

Endrin is produced via a multistep route from hexachlorocyclopentadiene. It begins by condensing vinyl chorlid with hexachlorocyclopentadiene. This product is then dehyrdochlorinated and followed by a reaction with cyclopentadiene. This forms isodrin which is then epoxidized by peracetic or perbenzoic acid to create endrin. [10] Endrin is also known as being a stereoisomer of dieldrin. [11]

Endrin was applied in many different ways. It was formulated into emulsifiable concentrates (ECs), wettable powders (WPs), granules, field strength dusts (FSDs), and pastes. It was then applied via high pressure spraying with a hand gun, spraying of orchard with an air blast, dusting potatoes, spraying row crops or application from an aircraft. [12]

Use

Endrin was formulated as emulsifiable concentrates (ECs), wettable powders (WPs), granules, field strength dusts (FSDs), and pastes. The product could then be applied by aircraft or by handheld sprayers in its various formulations. [12] Endrin has been used as an agriculture insecticide on tobacco, apple trees, cotton, sugar cane, rice, cereal, and grains. [13] It is effective against a variety of species such as: cotton boll worms, corn borers, cut worms and grass hoppers. [14] It has also been used to control rodents and birds. [15] As a pre-harvest treatment, endrin’s main use worldwide has been its application as a spray on cotton for the control of insects. In Australia, endrin is also used for insect control on tobacco. As a post-harvest treatment, endrin is sprayed onto the ground under the trees to control for rodents during autumn and spring. Its last use is as seed treatment. Cotton seeds in the United States and bean seeds in Australia are treated by endrin. [16] In Malaysia, a solution of endrin was used to rid mine pools and fish ponds of all fish prior to restocking.[17]

History

Endrin was first developed in 1950 by J. Hyman & Company and was used globally until the early 1970s. It was licensed to be manufactured by Shell International and Velsicol chemical companies. Production began in the United States by Shell and Velsicol and in the Netherlands by Shell. Due to its toxicity, it has been banned or severely restricted in many countries. In 1982, Shell discontinued the manufacturing of endrin.[10]

It was estimated that 2.3-4.5 million kilograms of endrin were sold in the USA in 1962. In 1970, Japan imported 72,000 kilograms of endrin. From 1963, Bali used 171 to 10,700 kilograms of endrin annually for the production of rice paddies until use of the compound was discontinued in 1972.[10] Taiwan reported to show higher levels of organochlorine pesticides including endrin, compared to other Asian countries such as Thailand and Vietnam. Over two million kilograms of organochlorine pesticides was estimated to be released into the environment annually in 1950s-1970s. Taiwan banned the use of endrin in 1989.

The Stockholm Convention on persistent organic pollutants that came in effect May 2004 listed endrin as one of the 12 initial persistent organic pollutants (POPs) that have been causing adverse effects on humans as well as the ecosystem. The convention required the participating parties to take measures to eliminate or restrict the production of POPs

Health Effects

Endrin is toxic with an LD50 of 3 mg/kg (oral, rat).[18] Acute endrin poisoning in humans affects primarily the nervous system. Food contaminated with endrin caused several clusters of poisonings worldwide, especially affecting children.[5] Orally ingested endrin is eliminated mostly in feces.[19][full citation needed] It is very toxic to aquatic organisms, namely fish, aquatic invertebrates, and phytoplankton. The U.S. EPA has set a freshwater acute criterion of 0.086 ug/L and a chronic criterion of 0.036 ug/L. In saltwater, the numbers are acute 0.037 and chronic 0.0023 ug/L.[20][full citation needed] Human health contaminate criterion for water plus organism is 0.059 ug/L.[21][full citation needed] Drinking water limits (maximum contaminant level (mcl)) is set to 2 ppb.[22][full citation needed]

Endrin is considered not classifiable as to carcinogenicity to humans by the United States National Toxicology Program (USNTP). The cyclodiene pesticides like chlordane, aldrin, dieldrin, and endrin are found to have much higher mammalian toxicity than other pesticides like DDT.

Environmental Issues

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