Endosulfan

Camille Esquivel Chemistry 11 Block C

=**My Organic Chemistry: Endosulfan** =


 * Endosulfan**, also spelled //Endosulphan//, is a highly persistent and toxic crystalline insecticide. Endosulfan is under the Cyclodiene subgroup of the of the organochloringe group of pesticides.


 * Other Names:** Benzoepin, Endocel, Parrysulfan, Phaser, Thiodan, Thionexv
 * IUPAC Name:** 1,4,5,6,7,7-hexachloro-8,9,10-trinorborn-5-en-2,3-ylenebismethylene sulfite //**OR**// 6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepine-3-oxide
 * Formula:** C 9 H 6 Cl 6 O 3 S



**How They Are Made:**
First introduced in the 1950’s, endosulfan is produced by the Diels-Alder reaction of hexachlorocyclopentadiene with //cis//-butene-1, 4-diol and subsequent reaction of the adduct with thionyl chloride. The Diels-Alder reaction is an organic chemical reaction where the 1, 4-addition of an alkene (the dienophile) to a conjugated diene creates diene synthesis.

**The reaction looks like this:**
+ (substituted) Olefin ** **(substituted) Cyclohexene** //*Diene is a hydrocarbon that contains two double bonds.//
 * conjugated (substituted) Diene*

**How It Benefits Us:**
Endosulfan is used in insecticides and acaricides. Insecticides are useful for they are chemical substances that can be applied to crops and soils to destroy harmful insects. Specifically, they are applied to crops of vegetables, fruits, paddy, cotton, cashew, tea, coffee, tobacco and timber. Another beneficial use of endosulfan is its ability to be used as a wood preservative (or else the wood is damaged as shown in the left picture) ==== which brings me to my next point, of acting as an acaricide. Acaricides are pesticides that kill mites and ticks (example shown in picture on the right), of which cause animal diseases and the spoilage of flour and other foods in storage. Endosulfan controls these mites (e.g. termites) that would usually damage wood. Therefore, this organic compound benefits us for it potentially removes any harmful bacteria, insects, mites and other substances that would contaminate the food we ingest and our world's resources.

How it Harms Us:
Endosulfan has been classified as Highly Hazardous by U.S. Environmental Protection Agency (EPA) and the European Union, and even Extremely Hazardous by the United Nations Environment Programme-Global Facility (UNEP-GEF).

When ingested by any creature, endosulfan acts as contact and stomach poison and has a slightTermites that endo fumigant action (evaporating nature); meaning it is harmful to humans! Humans can be exposed to endosulfan not only by direct ingestion but also by breathing air near where it has been sprayed, drinking water contaminated directly or through run-offs, being in contact with the contaminated soil, eating contaminated food, smoking cigarettes made from endosulfan contaminated tobacco, and working at endosulfan production centers. When the chemical has entered your system in any of the ways listed above, the results are harsh. From simply being poisoned and convulsion (contortion of the body, as seen on the image of the left and right), the effects are also fatal when inhaled, swallowed or absorbed through skin. Symptoms of poisoning include hyper activity, excitement, difficulty or stopping of breathing, salivation, loss of consciousness, diarrhea, anaemia, nausea, vomiting, insomnia, blurred vision, cyanosis, mouth foaming, tremor, dry mouth, lack of appetite, irritability, head ache, loss of memory, confusion, dizziness and lack of coordination. Other effects of endosulfan reported include cancer, damage to hormonal and central nervous systems, and epileptic seizures.

There have also been reported cases of the misuse of this chemical compound and is responsible for killing fish and snails, some intentional as applying endosulfan was a method used to remove unwanted fish from areas prior to restoration projects. To list some other animals that find endosulfan acutely toxic are bees, birds, crab larvae, earthworms, micro organisms (zooplanktons, phytoplankton, and soil algae), cats, dogs, sheep, and cattle.

**Other Interesting Facts/Information:**

 * The World Health Organization only classified endosulfan as Moderately Hazardous. This classification was then challenged and found incorrect to many other countries.
 * Used to be considered a //safer// alternative to other organochlorine pesticides in many countries!
 * Endosulfan is banned in the following 18 countries:
 * 1) Singapore
 * 2) Belize
 * 3) Tonga
 * 4) Syria
 * 5) Germany
 * 6) Sweden
 * 7) Philippines
 * 8) Netherlands
 * 9) St. Lucia
 * 10) Columbia
 * 11) Cambodia
 * 12) Bahrain
 * 13) Kuwait
 * 14) Oman
 * 15) Qatar
 * 16) Saudi Arabia
 * 17) United Arab Emirates
 * 18) Sri Lanka
 * Endosulfan is allowed for restricted use in the following 23 countries:
 * 1) Australia
 * 2) Bangladesh
 * 3) Indonesia
 * 4) Iran
 * 5) Japan
 * 6) Korea
 * 7) Kazakhstan
 * 8) Lithuania
 * 9) Thailand
 * 10) Taiwan
 * 11) Denmark
 * 12) Serbia & Montenegro
 * 13) Norway
 * 14) Finland
 * 15) Russia
 * 16) Venezuela
 * 17) Dominican Republic
 * 18) Honduras
 * 19) Panama
 * 20) Iceland
 * 21) Canada
 * 22) United States
 * 23) United Kingdom
 * One of the 21 priority compounds according to the UNEP-GEF in 2002.
 * In the Philippines, endosulfan was the cause for the largest number of deaths in 1991.

//"Acaricide". Answers - Sci-Tech Dictionary. June 3, 2010 .//
 * //Bibliography://**

//Allen, Stewart E., Grimshaw H. Max, and Parkinson John A.. __Chemical Analysis of Ecological Materials__. Oxford: Blackwell Scientific Publications, 1974.//

//"Convulsion | Define convulsion". Dictionary.com. June 3, 2010 .//

"Diene". Answers - Sci-Tech Dictionary. June 3, 2010 <[]>.

//"Endosulfan". Answers. June 3, 2010 .//

//S., Usha, and Harikrishnan V.R. "Endosulfan". International POPs Elimination Network. September 2005 .//

//Wood, Alan. "Endosulfan Data Sheet". Alan Wood. June 3, 2010 .//

//World Health Organization Expert Committee on Vector Biology and Control, __Chemistry and Specifications of Pesticides__. Geneva: World Health Organization, 1999.//