Dieldrin

Structural formula
General
Surname	Dieldrin
other names	1,2,3,4,10,10-hexachloro-6,7-epoxy-1,4,4a, 5,6,7,8,8a-octahydro-1,4-endo-5,8-exo- dimethanonaphthalene
Molecular formula	C 12 H 8 Cl 6 O
Brief description	white to yellowish solid with a naphthalene odor
External identifiers / databases
CAS number 60-57-1 EC number 200-484-5 ECHA InfoCard 100,000,440 PubChem 969491 Wikidata Q423992
properties
Molar mass	380.91 g mol −1
Physical state	firmly
density	1.75 g cm −3 (20 ° C)
Melting point	176-177 ° C
boiling point	decomposition
solubility	practically insoluble in water (<0.1 mg l −1 at 20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 300 + 310-351-372-410 P: 260-280-301 + 330 + 331 + 310-302 + 352 + 310-361 + 364
MAK	DFG / Switzerland: 0.25 mg m −3 (measured as inhalable dust )
Toxicological data	38.3 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 .

Dieldrin is a non-selective insecticide belonging to the group of chlorinated hydrocarbons , which has been used against soil insects and various disease-transmitting insects. It is also produced as a breakdown product of aldrin in plants and animals.

Environmental relevance and toxicity

Dieldrin is particularly toxic to fish. Dieldrin adheres very strongly to soil particles . The half-life in a temperate climate is about five years. Dieldrin is very likely to cause cancer . Studies show that dieldrin not only causes cancer , but also increases the mortality rate after diagnosis with continuous exposure (e.g. accumulation in the blood) .

Campaign against the fire ant

Under the direction of the US Department of Agriculture (USDA) attempts were made in the late 1950s to eradicate fire ants in the southern United States with the help of dieldrin. The announcement of the campaign in 1956 had already led to violent protests by nature conservation associations. The need for such an eradication program has been questioned, as has the planned approach. The USDA plans to distribute pellets made of a dieldrin- clay mixture over an area of ​​80,000 to 120,000 km ² . Implementation began at the end of 1957 and 1958. Fish and bird deaths and livestock and poultry deaths soon followed. The hunters complained about a decline in the number of wild birds that could be hunted. Fishermen in the Gulf of Mexico complained because crabs and shrimp died from dieldrin washed into the sea. In the "treated" areas, some species of snakes , lizards and frogs have been exterminated. The state of Alabama withdrew the funds already approved from the fire ant program in 1959, Florida did so in 1960. The other states affected by the fire ant no longer allowed the extermination program to be carried out.

Due to the damage that occurred when fighting the fire ant with dieldrin, funds for research into the environmental effects of pesticides were approved for the first time in 1958 .

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).

Prohibition

With the Stockholm Convention of May 22, 2001, a worldwide ban on the production, sale and use of twelve persistent organic pollutants ( POPs ) was passed. Under this " dirty dozen " ( dirty dozen ) is also dieldrin. On May 17, 2004, following ratification by the 50th Accession State , the Convention became globally valid.

Individual evidence

1. ↑ ^{a b c d e f g h} Entry on Dieldrin in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
2. ↑ Entry on Dieldrin 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 .
3. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 60-57-1 or Dieldrin ), accessed on November 2, 2015.
4. ↑ Entry on dieldrin in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 31, 2018 or earlier.
5. ↑ AP Høyer, T. Jørgensen, JW Brock, P. Grandjean: Organochlorine exposure and breast cancer survival. In: Journal of Clinical Epidemiology. 53 (2000), pp. 323-330.
6. ↑ P. Olaya-Contreras, J. Rodriguez-Villamil, HJ Posso-Valencia, JE Cortez: Organochlorine exposure and breast cancer risk in Colombian women. In: Cad Saude Publica. 14, pp. 125-132 (1998).
7. ^ I. Romieu, M. Hernandez-Avila, E. Lazcano-Ponce, J. Weber, E. Dewailly: Breast cancer, lactation history, and serum organochlorines. In: Am J Epidemiol. 152 (2000), pp. 363-370.
8. ^ Thomas R. Dunlap: DDT: Scientists, Citizens and Public Policy. Princeton University Press, 1981, ISBN 0-691-04680-8 , chap. 4th
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.