Aldrin

Structural formula
General
Surname	Aldrin
other names	1,2,3,4,10,10-hexachloro-1,4,4a, 5,8,8a-hexahydro-1,4- endo -5,8- exo -dimethanonaphthalene; (1 R , 2 R , 3 R , 6 S , 7 S , 8 S ) -1,8,9,10,11,11-hexachlortetracyclo [6.2.1.1 3,6 .0 2,7 ] dodeca-4, 9-dien;
Molecular formula	C 12 H 8 Cl 6
Brief description	brown to white odorless crystals
External identifiers / databases
EC number	206-215-8
ECHA InfoCard	100.005.652
PubChem	12310947
Wikidata	Q409054
properties
Molar mass	364.91 g mol −1
Physical state	firmly
density	1.7 g cm −3
Melting point	105 ° C
boiling point	145 ° C (2.7 hPa)
Vapor pressure	3.1 m Pa (20 ° C)
solubility	practically insoluble in water (0.05 mg l −1 at 20 ° C)
safety instructions
H and P phrases	H: 300-310-351-372-410
	P: 210-273-280-305 + 351 + 338
MAK	DFG / Switzerland: 0.25 mg m −3 (measured as inhalable dust )
Toxicological data	39 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Aldrin is an insecticide that has been used against termites , grasshoppers and wireworms , among other things . It is converted into dieldrin by plants and animals . The use of Aldrin was banned in Germany in 1981, and since the Stockholm Convention came into force in 2004 , it has been banned worldwide. It is named after Kurt Alder , who co-discovered the Diels-Alder reaction .

history

Its use was severely restricted in Germany as early as 1971 due to persistence and accumulation in the food chain and was finally banned in 1981. The Stockholm Convention of May 22, 2001 ratified a worldwide ban on the manufacture, sale and use of twelve persistent organic pollutants (POP). Among that " dirty dozen " is Aldrin. With the ratification by the 50th acceding country on May 17, 2004, the Convention acquired global legal validity.

synthesis

Aldrin is a Diels-Alder reaction of norbornadiene (which, in turn, by a Diels-Alder reaction of cyclopentadiene and acetylene is produced) and hexachlorocyclopentadiene synthesized.

use

In Germany, Aldrin was mainly used against pests living in the soil, especially wireworms, white grubs and the meadow snake . It was also used as a dressing agent for seeds . It was marketed as a component of wettable powders, granulates, seed powders or dust preparations.

toxicology

When working with Aldrin, the inhalation of dusts or vapors and absorption through the skin were the most common routes of absorption. Aldrin has a strong neurotoxic effect; headaches, dizziness and muscle twitching often occur in acute poisoning. In the case of severe acute poisoning, tonic-clonic spasms and impaired consciousness also occur. In addition, severe cardiovascular reactions, fever or low temperature can occur, liver or kidney function can be impaired, and leukocytosis can also occur. The lethal dose for an adult human with a single oral intake has been estimated to be approximately 5 g.

In the body, aldrin is converted into dieldrin . The dieldrin is further oxidized in the liver to form a hydrophilic compound which, after glucuronidation , can be excreted in the urine. However, the conversion of the dieldrin proceeds only slowly, it accumulates in the fatty tissue. The half-life for elimination of dieldrin in humans has been estimated to be about one year.

Repeated uptake of small amounts of aldrin can result in symptoms of poisoning similar to those of acute poisoning due to the dieldrin enrichment. Symptoms of poisoning are to be expected from around 150 to 200 µg dieldrin per liter of blood. In long-term feeding studies with different animal species, liver damage, damage to the central nervous system, kidney damage or immunosuppressive effects occurred, depending on the species, from around 0.05 mg Aldrin per kg body weight and day.

Embryonic malformations ( teratogenic effects and foetotoxicity) only occurred when pregnant animals received an acutely toxic dose of Aldrin. Aldrin is very likely to cause cancer . Liver tumors increased in mice after administration of Aldrin, which could not be reproduced in other animal species. In contrast, there are no indications of a genotoxic or mutagenic effect. The LD ₅₀ in rats is 39 mg / kg when administered orally . The direct connection between aldrin / dieldrin accumulation in the blood and breast cancer is still controversial. However, some studies confirm both the increased risk of breast cancer and the more severe course of the disease after long-term exposure to aldrin or dieldrin. Aldrin is very toxic to fish and bees .

Analytical evidence

The chemical-analytical detection in environmental samples, food and animal feed is carried out after suitable sample preparation to separate the matrix and gas chromatographic separation of minor components by high-resolution mass spectrometry techniques such as flight mass spectrometry (Time-Of-Flight mass spectrometry).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on Aldrin in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
↑ Entry on Aldrin in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Data sheet Aldrin solution 100 μg / mL in acetonitrile, PESTANAL at Sigma-Aldrich , accessed on October 24, 2016 ( PDF ).
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 309-00-2 or Aldrin ), accessed on November 2, 2015.
↑ Entry on Aldrin in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 28, 2019.
↑ L. Roth, G. Rupp, M. Wißfeld: Chlorinated hydrocarbons - properties, environmental relevance, toxicity, therapy, regulations, handling, storage, disposal. ecomed Sicherheit, 2007, ISBN 6096513002 .
↑ Werner Perkow: Active substances in pesticides and pesticides. 2nd Edition. Paul Parey Publishing House.
^ Dieldrin and Aldrin. In: Breast Cancer Prevention Partners (BCPP). Retrieved March 19, 2019 (American English).
↑ Eric J. Reiner, Adrienne R. Boden, Tony Chen, Karen A. MacPherson and Alina M. Muscalu: Advances in the Analysis of Persistent Halogenated Organic Compounds . In: LC GC Europe . 23 (2010) 60-70.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on Aldrin in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

[CLP_100.005.652-2] Entry on Aldrin in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[Sigma-3] Data sheet Aldrin solution 100 μg / mL in acetonitrile, PESTANAL at Sigma-Aldrich , accessed on October 24, 2016 ( PDF ).

[4] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 309-00-2 or Aldrin ), accessed on November 2, 2015.

[5] Entry on Aldrin in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 28, 2019.

[ecomed-6] L. Roth, G. Rupp, M. Wißfeld: Chlorinated hydrocarbons - properties, environmental relevance, toxicity, therapy, regulations, handling, storage, disposal. ecomed Sicherheit, 2007, ISBN 6096513002 .

[Perkow-7] Werner Perkow: Active substances in pesticides and pesticides. 2nd Edition. Paul Parey Publishing House.

[8] Dieldrin and Aldrin. In: Breast Cancer Prevention Partners (BCPP). Retrieved March 19, 2019 (American English).

[Reiner-9] Eric J. Reiner, Adrienne R. Boden, Tony Chen, Karen A. MacPherson and Alina M. Muscalu: Advances in the Analysis of Persistent Halogenated Organic Compounds . In: LC GC Europe . 23 (2010) 60-70.