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Parathion

 

Parathion

Parathion
Names
IUPAC name
O,O-Diethyl O-(4-nitrophenyl) phosphorothioate
Other names
E605
Identifiers
 Y
ChEBI  N
ChEMBL  Y
ChemSpider  Y
Jmol-3D images Image
KEGG  Y
UNII  Y
Properties
C10H14NO5PS
Molar mass 291.26 g·mol−1
Appearance White crystals (pure form)
Melting point 6 °C (43 °F; 279 K)
24 mg/L
Solubility in other solvents high solubility

in xylene and butanol

Hazards
Safety data sheet [1]
Very Toxic T+ Dangerous for the Environment (Nature) N
R-phrases R50/53
S-phrases S28, S36/37, S45, S60, S61
NFPA 704
1
4
2
Flash point 120 °C (248 °F; 393 K)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)
5 mg/kg (mouse, oral)
10 mg/kg (rabbit, oral)
3 mg/kg (dog, oral)
0.93 mg/kg (cat, oral)
5 mg/kg (horse, oral)
8 mg/kg (guinea pig, oral)
2 mg/kg (rat, oral)[1]
84 mg/m3 (rat, 4 hr)[1]
50 mg/m3 (rabbit, 2 hr)
14 mg/m3 (guinea pig, 2 hr)
15 mg/m3 (mouse)[1]
US health exposure limits (NIOSH):
PEL (Permissible)
none (methyl parathion),[2] TWA 0.1 mg/m3 [skin] (ethyl parathion)[3]
REL (Recommended)
TWA 0.2 mg/m3 [skin] (methyl parathion)[2] TWA 0.05 mg/m3 [skin] (ethyl parathion)[3]
N.D. (methyl parathion)[2] 10 mg/m3 (ethyl parathion)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: Y/N?)

Parathion, also called parathion-ethyl or diethyl parathion and locally known as "Folidol", is an insecticide and acaricide. It was originally developed by IG Farben in the 1940s. It is highly toxic to non-target organisms, including humans. Its use is banned or restricted in many countries, and there are proposals to ban it from all use.

Contents

  • Parathion-methyl 1
  • History 2
  • Handling properties 3
  • Industrial synthesis 4
  • Applications 5
  • Insecticidal activity 6
  • Degradation 7
  • Safety 8
    • Protection against poisoning 8.1
  • Proposals to ban 9
  • See also 10
  • References 11
  • External links 12

Parathion-methyl

"Parathion-methyl" (CAS#298-00-0), also known as methyl parathion or dimethyl parathion, was also developed and is marketed for similar uses. It is a distinct compound with diminished toxicity. Some trade names of parathion-methyl include Bladan M, Metaphos, ME605, and E601.

Ball-and-stick model of the methyl parathion molecule

History

Bottle with E605

Parathion was developed by Gerhard Schrader for the German trust IG Farben in the 1940s. After the war and the collapse of IG Farben due to the war crime trials, the Western allies seized the patent, and parathion was 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").

Handling properties

When pure, parathion is a white crystalline solid, however it is commonly distributed as a brown liquid that smells of rotting eggs or garlic. The insecticide is more or less stable, although it darkens when exposed to sunlight.

Industrial synthesis

Parathion is synthesized from diethyl dithiophosphoric acid (C2H5O)2PS2H, which is obtained by treatment of P2S5 with ethanol (methanol is used to prepare methyl parathion). Diethyl dithiophosphoric acid is chlorinated to generate diethylthiophosphoryl chloride, which is then treated with sodium 4-nitrophenolate (the sodium salt of 4-nitrophenol).[5]

2 (C2H5O)2P(S)SH + 3 Cl2 → 2 (C2H5O)2P(S)Cl + S2Cl2 + 2 HCl
(C2H5O)2P(S)Cl + NaOC6H4NO2 → (C2H5O)2P(S)OC6H4NO2 + NaCl

Applications

As a pesticide, parathion is generally applied by spraying. It is often applied to 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.

Insecticidal activity

Parathion acts on the enzyme acetylcholinesterase, but indirectly. After being ingested by insects (and unintentionally, by humans), the parathion becomes oxidized by oxidases to give paraoxon, replacing the double bonded sulfur with oxygen.[6]

(C2H5O)2P(S)OC6H4NO2 + 1/2 O2 → (C2H5O)2P(O)OC6H4NO2 + S

The phosphate ester is more reactive in organisms than the phosphorothiolate ester, as the phosphorus atoms become much more electropositive.[6]

Degradation

Degradation of parathion leads to more water-soluble products. Hydrolysis, which deactivates the molecule, occurs at the aryl ester bond resulting in diethyl thiophosphate and 4-nitrophenol.[6]

(C2H5O)2P(S)OC6H4NO2 + H2O → HOC6H4NO2 + (C2H5O)2P(S)OH

Degradation proceeds differently under anaerobic conditions: the nitro group on parathion is reduced to the amine.

(C2H5O)2P(S)OC6H4NO2 + 6 H → (C2H5O)2P(S)OC6H4NH2 + 2 H2O

Safety

Parathion is a cholinesterase inhibitor. It generally disrupts the nervous system by inhibiting acetylcholinesterase. It is absorbed via skin, mucous membranes, and orally. Absorbed parathion is rapidly metabolized to paraoxon, as described above. 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. 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 recommended that small frequently repeated doses be used in treatment. If human poisoning is detected early and the treatment is prompt (atropine and artificial respiration), fatalities are infrequent. Insufficient oxygen will lead to cerebral hypoxia and permanent brain damage. Peripheral neuropathy including paralysis is noticed as late sequelae after recovery from acute intoxication. Parathion has been used for committing suicide and deliberately poisoning other persons. It is known as "Schwiegermuttergift" (mother-in-law poison) in Germany. For this reason, most formulations contain a blue dye providing warning.

Parathion has been used as a chemical weapon, most notably by the Selous Scouts during the Rhodesian Bush War.[7]

Based on animal studies, parathion is considered by the U.S. Environmental Protection Agency to be a possible human carcinogen.[8] Studies show that parathion is toxic to fetuses, but does not cause birth defects.[9]

It is classified as a WHO Toxicity Class, "Ia, Extremely Hazardous".

Parathion is very toxic to bees, fish, birds, and other forms of wildlife.[9]

Protection against poisoning

To provide the end user with a minimum standard of protection, suitable protective gloves, clothing, and a respirator with organic-vapour cartridges must be worn. 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 paying careful attention to personal hygiene. Frequent analysis of workers' serum acetylcholinesterase activity is also helpful with regards to occupational safety, because the action of parathion is cumulative. If an area of the body is contaminated with parathion, the contamination should be removed immediately and thoroughly. Also, atropine has been used as a specific antidote.

Proposals to ban

According to the non-governmental organisation

External links

  1. ^ a b c "Parathion". Immediately Dangerous to Life and Health.  
  2. ^ a b c "NIOSH Pocket Guide to Chemical Hazards #0427".  
  3. ^ a b c "NIOSH Pocket Guide to Chemical Hazards #0479".  
  4. ^ http://www.ehs.neu.edu/laboratory_safety/general_information/nfpa_hazard_rating/documents/NFPAratingJR.htm
  5. ^ Fee, D. C.; Gard, D. R.; Yang, C. (2005). "Phosphorus Compounds". Kirk-Othmer Encyclopedia of Chemical Technology. New York: John Wiley & Sons.  
  6. ^ a b c Metcalf, R. L. (2002). "Insect Control". Ullman’s Encyclopedia of Industrial Chemistry. New York: Wiley-VCH Verlag GmbH & Co. KGaA.  
  7. ^ Moorcraft, Paul; McLaughlin, Peter (2008). The Rhodesian War: A Military History. Yorkshire: Pen & Sword. p. 106.  
  8. ^ "Parathion". Integrated Risk Information System.  
  9. ^ a b "Pesticide Information Profiles - Parathion". Extension Toxicology Network.  
  10. ^ a b S. Kegley, B. Hill, S. Orme. "Parathion - Identification, toxicity, use, water pollution potential, ecological toxicity and regulatory information".  

References

See also

[10]

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