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Dieldrin
 
 
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Dieldrin is a chlorinated hydrocarbon originally produced in 1948 by J. Hyman & Co, Denver, as an insecticide
Insecticide

An insecticide is a pesticide used against insects in all developmental forms. They include ovicides and larvicides used against the Egg and larvae of insects respectively....
. The molecule has a ring structure based on naphthalene
Naphthalene

Naphthalene, also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or antimite and not to be confused with naphtha, is a crystalline, Aromaticity, white, solid hydrocarbon with formula Carbon10hydrogen8 and the structure of two fused benzene rings....
.

Dieldrin is closely related to aldrin
Aldrin

Aldrin is an organochlorine compound insecticide which is redox in the insect to form dieldrin, a neurotoxin. Aldrin was formerly used to kill soil insects such as termites and grasshoppers to protect crops such as corn and potatoes....
 which itself breaks down to form dieldrin. Aldrin is not toxic to insects, it is oxidised in the insect to form dieldrin which is the active compound. Both dieldrin and aldrin are named after the Diels-Alder reaction
Diels-Alder reaction

The Diels-Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system....
 which is used to form aldrin from a mixture of norbornadiene and hexachlorocyclopentadiene.

Originally developed in the 1940s as an alternative to DDT
DDT

DDT is one of the best known synthetic pesticides. It is a chemical with a long, unique, and controversial history.First synthesized in 1874, DDT's insecticidal properties were not discovered until 1939....
, dieldrin proved to be a highly effective insecticide and was very widely used during the 1950s to early 1970s.






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Encyclopedia


Dieldrin is a chlorinated hydrocarbon originally produced in 1948 by J. Hyman & Co, Denver, as an insecticide
Insecticide

An insecticide is a pesticide used against insects in all developmental forms. They include ovicides and larvicides used against the Egg and larvae of insects respectively....
. The molecule has a ring structure based on naphthalene
Naphthalene

Naphthalene, also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or antimite and not to be confused with naphtha, is a crystalline, Aromaticity, white, solid hydrocarbon with formula Carbon10hydrogen8 and the structure of two fused benzene rings....
.

Dieldrin is closely related to aldrin
Aldrin

Aldrin is an organochlorine compound insecticide which is redox in the insect to form dieldrin, a neurotoxin. Aldrin was formerly used to kill soil insects such as termites and grasshoppers to protect crops such as corn and potatoes....
 which itself breaks down to form dieldrin. Aldrin is not toxic to insects, it is oxidised in the insect to form dieldrin which is the active compound. Both dieldrin and aldrin are named after the Diels-Alder reaction
Diels-Alder reaction

The Diels-Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system....
 which is used to form aldrin from a mixture of norbornadiene and hexachlorocyclopentadiene.

Originally developed in the 1940s as an alternative to DDT
DDT

DDT is one of the best known synthetic pesticides. It is a chemical with a long, unique, and controversial history.First synthesized in 1874, DDT's insecticidal properties were not discovered until 1939....
, dieldrin proved to be a highly effective insecticide and was very widely used during the 1950s to early 1970s. Endrin
Endrin

Endrin is a cyclodiene insecticide used on cotton, maize, and rice. It also acts as an avicide. As a rodenticide, it is used to control mouse and voles....
 is a stereoisomer of dieldrin.

However, it is an extremely persistent organic pollutant
Persistent organic pollutant

Persistent organic pollutants are organic compounds that are resistant to environmental degradation through chemical decomposition, biodegradation, and photolysis processes....
, it does not easily break down
Biodegradation

Biodegradation is the process by which organic compound substances are decomposition by the enzymes produced by living organisms. The term is often used in relation to ecology, waste management and natural environmental environmental remediation ....
. Furthermore it tends to biomagnify as it is passed along the food chain
Food chain

Food chains, also called, food networks and/or trophic social networks, describe the eating relationships between species within an ecosystem....
. Long-term exposure has proven toxic to a very wide range of animals including humans, far greater than to the original insect targets. For this reason it is now banned
Ban (law)

For the policy on Wikipedia, see Wikipedia:Banning policy.A ban is, generally, any decree that Prohibitions something.Bans are formed for the prohibition of activities within a certain political territory....
 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 can also adversly affect testicular descent in the fetus if a pregnant woman is exposed to Dieldrin.

Synthesis


It can be formed from the synthesis of hexachloro-1,3-cyclopentadiene with norbornadiene
Norbornadiene

Norbornadiene is a bicyclic hydrocarbon. The molecule can be envisioned as a 1,4-cyclohexadiene bridged in the aromatic para position positions by a methylene group....
 in a Diels-Alder reaction
Diels-Alder reaction

The Diels-Alder reaction is an organic chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system....
, followed by epoxidation of the norbornene ring.




See also

  • Aldrin
    Aldrin

    Aldrin is an organochlorine compound insecticide which is redox in the insect to form dieldrin, a neurotoxin. Aldrin was formerly used to kill soil insects such as termites and grasshoppers to protect crops such as corn and potatoes....
  • Endrin
    Endrin

    Endrin is a cyclodiene insecticide used on cotton, maize, and rice. It also acts as an avicide. As a rodenticide, it is used to control mouse and voles....


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