Parathion
From Wikipedia, the free encyclopedia
| Parathion | |
|---|---|
 |
|
| IUPAC name | O,O-Diethyl-O-4-nitro-phenylthiophosphate |
| Other names | E605 |
| Identifiers | |
| CAS number | [56-38-2] |
| SMILES | C(C)OP(OCC)(=S)Oc1
(ccc([N+1]([O-1])=O)cc1) |
| Properties | |
| Molecular formula | C10H14NO5PS |
| Molar mass | 291,3 g/mol |
| Appearance | White crystals (pure form) |
| Melting point |
6 °C |
| Solubility in water | 24mg/l in water, high solubility
in xylene or n-butanole |
| Hazards | |
| MSDS | [1] |
| R-phrases | R24, R26/28, R48/25, R50/53 |
| S-phrases | S28, S36/37, S45, S60, S61 |
| Flash point | 120 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
|
Parathion, also called parathion-ethyl or diethyl parathion, is an organophosphate compound. Like many other organophosphate insecticides, it is a very potent insecticide and acaricide. It was originally developed by IG Farben in the 1940s. It is highly toxic to non-target organisms. Its use is banned or restricted in many countries, and there are proposals to ban it from all use.
Contents |
[edit] History
Parathion was developed by the German trust IG Farben in the 1940s. Dr. Gerhard Schrader was the inventor. After the war the Western allies seized the according patent and parathion was thereafter marketed worldwide by different companies and under different brand names. The most common German brand was E605 (banned in Germany after 2002); this was not a food-additive "E number" as used in the EU today. "E" stands for Entwicklungsnummer (German for "development number"), not for "European".
[edit] Properties
In its purest form, parathion consists of white crystals; however more commonly distributed forms take the form of a brown liquid which smells of rotting eggs or garlic. The insecticide is more or less stable, though it darkens when exposed to sunlight.
[edit] Industrial Synthesis
Parathion is synthesized in two steps from diethyl dithiophosphoric acid, which is obtained by treatment of P2S5 with ethanol. In the first step, diethyl dithiophosphate is chlorinated to generate diethylthiophosphoryl chloride. The diethyl dithiophosphoric acid is then treated with sodium p-nitrophenolate at elevated temperatures for extended periods of time.[1]
- 2(C2H5O)2P(S)SH + 3Cl2 → 2(C2H5O)2P(S)Cl +S2Cl2 + 2HCl
- (C2H5O)2P(S)Cl + NaOC6H4NO2 → (C2H5O)2P(S)OC6H4NO2 + NaCl
[edit] Applications
As a pesticide, parathion is generally applied by spraying, and often used on cotton, rice and fruit trees. The usual concentrations of ready-to-use solutions are 0.05 to 0.1%. The chemical is banned for use on many food crops.[citation needed]
[edit] Insecticidal Activity
Parathion acts on the enzyme acetylcholinesterase, but indirectly. After being ingested by insects, the parathion becomes oxidized by oxidases to give paraoxon, replacing the double bonded sulfur with oxygen.[2]
- (C2H5O)2P(S)OC6H4NO2 → (C2H5O)2P(O)OC6H4NO2
The phosphate ester is more reactive in organisms than the phosphorothiolate ester, as the phosphorus atoms become much more electronegative.[2]
[edit] Degradation
Degradation of parathion leads to more water soluble products. Hydrolysis degrades and deactivates the molecule. Hydrolysis occurs at the aryl ester bond resulting in diethylphosphate and 4-nitrophenol.[2]
(C2H5O)2P(S)OC6H4NO2 + H2O → HOC6H4NO2 + (C2H5O)2P(S)O- + H+
Under anaerobic conditions, degradation proceeds differently; the nitrate group on parathion is reduced to the amine.
(C2H5O)2P(S)OC6H4NO2 → (C2H5O)2P(S)OC6H4NH2
[edit] Safety
Parathion is a cholinesterase inhibitor. It generally disrupts neural function by inhibiting the essential enzyme acetylcholinesterase. It is absorbed via skin, mucous membranes, and orally. Absorbed Parathion is rapidly metabolized to Paraoxon in which the sulfur atom is replaced by oxygen. Paraoxon exposure can result in headaches, convulsions, poor vision, vomiting, abdominal pain, severe diarrhea, unconsciousness, tremor, dyspnea and finally lung-edema as well as respiratory arrest.[citation needed]
Symptoms of poisoning are known to last for extended periods of time, sometimes months. The most common and very specific antidote is atropine in doses of up to 100 mg daily. Because atropine may also be toxic, it is now recommended to use small doses which are frequently repeated. If human poisoning is detected early and the treatment is prompt (antidote and artificial respiration), fatalities are infrequent. Insufficient respiration may lead to cerebral hypoxia and permanent brain damage. Additionally, peripheral neuropathy including paralysis is noticed as late sequelae after recovery from acute intoxication.[citation needed] Parathion has been extensively used for committing suicide and deliberately killing other persons.[citation needed] For the latter reason most formulations contain a blue dye providing warning.
Based on animal studies, Parathion is considered by the US EPA to be a possible human carcinogen.[3] Studies show that Parathion is toxic to fetuses, but does not cause birth defects.[4]
Parathion is very toxic to bees, fish, birds, and other forms of wildlife.[4] Parathion can be replaced by many safer and less toxic alternatives (less toxic organophosphates, carbamates, or synthetic pyrethroids).[citation needed]
[edit] Protection against poisoning
To assure human protection the end user must wear protective gloves, clean protective clothing, and a respirator of the organic-vapour type when handling this material. He/she should bathe immediately after work. Industrial safety during the production process requires special ventilation and continuous measurement of air contamination in order not to exceed PEL levels as well as keeping personal hygiene. Frequent determination of workers' serum acetylcholinesterase activity is also helpful in regards of occupational safety, because the action of Parathion is cumulative. If an area of the body is contaminated with parathion, if possible, it should be removed immediately. Also, atropine may be used as a specific antidote.[citation needed]
[edit] Proposals to ban
According to the non-governmental organisation Pesticide Action Network or PAN, parathion is one of the most dangerous pesticides. This organization lists Parathion also as 'bad actor chemical'.[5] In the US alone more than 650 agricultural workers have been poisoned since 1966, of which 100 died.[citation needed] In underdeveloped countries many more people have suffered fatal and nonfatal intoxications. The World Health Organization, PAN and numerous environmental organisations propose a general and global ban.[citation needed] Its use is banned or restricted in 23 countries and its import is illegal in a total of 50 countries.[5]
[edit] Parathion-methyl
A second compound of this chemical group, parathion-methyl, was also developed and marketed for similar uses. It is a distinct compound from parathion; its IUPAC name is O,O-dimethyl O-4-nitrophenyl phosphorothioate, with a molecular formula of C8H10NO5PS. Its CAS No. is 298-00-0.
Other names for parathion-methyl include methyl parathion and dimethyl parathion; some trade names include Bladan M, Metaphos, ME605, and E601.
[edit] See also
[edit] References
- ^ Fee, D. C.; Gard, D. R.; Yang, C. “Phosphorus Compounds” Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons: New York, 2005. doi:10.1002/0471238961.16081519060505.a01.pub2.
- ^ a b c Metcalf, R. L. “Insect Control” Ullman’s Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co. KGaA: New York, 2002. doi:10.1002/14356007.a14_263 10.1002/14356007.a14_263.
- ^ Parathion. Integrated Risk Information System. U. S. Environmental Protection Agency (26 Jan 2007).
- ^ a b Pesticide Information Profiles - Parathion. Extension Toxicology Network. Oregon State University (September 1993).
- ^ a b S. Kegley, B. Hill, S. Orme. Parathion - Identification, toxicity, use, water pollution potential, ecological toxicity and regulatory information. Pesticide Action Network.
[edit] External links
- ATSDR - Methyl Parathion Expert Panel Report U.S. Department of Health and Human Services (public domain)
- International Chemical Safety Card 0006 (Ethyl parathion)
- International Chemical Safety Card 0626 (Methyl parathion)
