parathion

パラチオン

　 　

WordNet

1. a colorless and odorless toxic oil used as an insecticide
2. a toxic condition resulting from inhalation or ingestion of the insecticide parathion; characterized by nausea and abdominal pains and headache and convulsions and sweating

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1. パラチオン(殺虫剤として用いる)

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/10/24 03:16:31」(JST)

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Parathion

Names
IUPAC name O,O-Diethyl O-(4-nitrophenyl) phosphorothioate
Other names E605
Identifiers
CAS Number	56-38-2 Y
ChEBI	CHEBI:27928 N
ChEMBL	ChEMBL261919 Y
ChemSpider	13844817 Y
ECHA InfoCard	100.000.247
Jmol 3D model	Interactive image
KEGG	C06604 Y
UNII	61G466064D Y
InChI InChI=1S/C10H14NO5PS/c1-3-14-17(18,15-4-2)16-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3 Y Key: LCCNCVORNKJIRZ-UHFFFAOYSA-N Y InChI=1/C10H14NO5PS/c1-3-14-17(18,15-4-2)16-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3 Key: LCCNCVORNKJIRZ-UHFFFAOYAR
SMILES S=P(Oc1ccc(cc1)[N+]([O-])=O)(OCC)OCC
Properties
Chemical formula	C10H14NO5PS
Molar mass	291.26 g·mol−1
Appearance	White crystals (pure form)
Melting point	6 °C (43 °F; 279 K)
Solubility in water	24 mg/L
Solubility in other solvents	high solubility in xylene and butanol
Hazards
Safety data sheet	[1]
EU classification (DSD)	T+ N
R-phrases	R24, R26/28, R48/25, 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)
LC50 (median concentration)	84 mg/m3 (rat, 4 hr)
LCLo (lowest published)	50 mg/m3 (rabbit, 2 hr) 14 mg/m3 (guinea pig, 2 hr) 15 mg/m3 (mouse)
US health exposure limits (NIOSH):
PEL (Permissible)	none (methyl parathion), TWA 0.1 mg/m3 [skin] (ethyl parathion)
REL (Recommended)	TWA 0.2 mg/m3 [skin] (methyl parathion) TWA 0.05 mg/m3 [skin] (ethyl parathion)
IDLH (Immediate danger)	N.D. (methyl parathion) 10 mg/m3 (ethyl parathion)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Parathion, also called parathion-ethyl or diethyl parathion and locally known as "Folidol", is an organophosphate compound possessing a organothiophosphate group. It is a potent 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. The basic structure is shared by parathion methyl.

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").It is an Irreversible Ach Inhibitor Safety concerns lead to the development of parathion methyl, which is somewhat less toxic.

Handling properties

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

Industrial synthesis

Parathion is synthesized from diethyl dithiophosphoric acid (C₂H₅O)₂PS₂H by chlorination to generate diethylthiophosphoryl chloride ((C₂H₅O)₂P(S)Cl). In a salt metathesis reaction, the chloride treated with sodium 4-nitrophenolate (the sodium salt of 4-nitrophenol).

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 indirectly. After an insect (or a human) ingests parathion, an oxidase replaces the double bonded sulfur with oxygen to give paraoxon.

(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.

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.

(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 in Insecticidal activity. 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, 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 and related organophosphorus pesticides are used in hundreds of thousands of poisonings annually, especially suicides. 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.

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

It is classified as a UNEP Persistent Organic Pollutant and WHO Toxicity Class, "Ia, Extremely Hazardous".

Parathion is toxic to bees, fish, birds, and other forms of wildlife.

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 is normally 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 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. Also, atropine has been used as a specific antidote.

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 a 'bad actor chemical'. In the US alone more than 650 agricultural workers have been poisoned since 1966, of which 100 died. 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. Its use is banned or restricted in 23 countries and its import is illegal in a total of 50 countries.

See also

• Pesticide toxicity to bees
• Parathion methyl

References

External links

• Parathion in the Pesticide Properties DataBase (PPDB)
• ATSDR - Methyl Parathion Expert Panel Report U.S. Department of Health and Human Services (public domain)
• CDC - NIOSH Pocket Guide to Chemical Hazards U.S. Department of Health and Human Services (public domain)
• Ethyl parathion: International Chemical Safety Card 0006
• Methyl parathion: International Chemical Safety Card 0626

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

• 1. 有機リン剤およびカルバメート中毒 organophosphate and carbamate poisoning
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• 3. 米国における労働衛生および環境衛生に関する問題についての情報および教材 information and educational resources for occupational and environmental health issues in the united states
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English Journal

• The influence of tomato processing on residues of organochlorine and organophosphate insecticides and their associated dietary risk.

• Reiler E1, Jørs E2, Bælum J2, Huici O3, Alvarez Caero MM4, Cedergreen N1.
• The Science of the total environment.Sci Total Environ.2015 Sep 15;527-528:262-9. doi: 10.1016/j.scitotenv.2015.04.081. Epub 2015 May 14.
• Due to the increasing food demand, the use of pesticides in agriculture is increasing. Particularly in low income countries poor training among farmers, combined with the use of obsolete pesticides may result in a high risk for the consumers. In this study six organochlorines and five organophosphat
• PMID 25965039

• Determination of pesticides in lettuce using solid-liquid extraction with low temperature partitioning.

• Costa AI1, Queiroz ME2, Neves AA1, de Sousa FA1, Zambolim L3.
• Food chemistry.Food Chem.2015 Aug 15;181:64-71. doi: 10.1016/j.foodchem.2015.02.070. Epub 2015 Feb 20.
• This work describes the optimization and validation of a method employing solid-liquid extraction with low temperature partitioning (SLE/LTP) together with analysis by gas chromatography with electron capture detection (GC/ECD) for the determination of nine pesticides (chlorothalonil, methyl parathi
• PMID 25794722

• Correction to: "Constitutive Androgen Receptor-Null Mice Are Sensitive to the Toxic Effects of Parathion: Association with Reduced Cytochrome P450-Mediated Parathion Metabolism".

• [No authors listed]
• Drug metabolism and disposition: the biological fate of chemicals.Drug Metab Dispos.2015 Aug;43(8):1285. doi: 10.1124/dmd.115.032961err.
• PMID 26126545

Japanese Journal

• 2-アミノエタノールの存在下でのメチルパラチオンの加水分解除去: 反応速度論的研究

• 日本農薬学会誌（Ｊｏｕｒｎａｌ　ｏｆ　Ｐｅｓｔｉｃｉｄｅ　Ｓｃｉｅｎｃｅ） 43(1), 41-46, 2018
• NAID 130006406004

• Determination of Eleven Organophosphorus Pesticide Residues in Textiles by Using HPLC-HRMS

• Analytical Sciences 33(9), 1027-1032, 2017
• NAID 130006071170

• Effects of Exposure to Methyl Parathion on Egg Hatchability and Eggshell Chemical Composition in Podocnemis expansa (Testudines, Podocnemididae)

• Zoological science 32(2), 135-140, 2015-04
• NAID 40020424286

Related Links

• Parathion - Wikipedia, the free encyclopedia

Parathion, also called parathion-ethyl or diethyl parathion, is an organophosphate compound. It is a potent insecticide and acaricide. It was originally developed by IG Farben in the 1940s. It is highly toxic to non-target organisms, including ...

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