Malathion
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| Structural formula without specifying the stereochemistry | ||||||||||||||||||||||
| General | ||||||||||||||||||||||
| Surname | Malathion | |||||||||||||||||||||
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| Molecular formula | C 10 H 19 O 6 PS 2 | |||||||||||||||||||||
| Brief description |
colorless or yellow-brown oily liquid with a garlic-like odor |
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| properties | ||||||||||||||||||||||
| Molar mass | 330.36 g mol −1 | |||||||||||||||||||||
| Physical state |
liquid |
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| density |
1.21 g cm −3 |
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| Melting point |
2.85 ° C |
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| boiling point |
156-157 ° C (931 Pa ) |
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| Vapor pressure |
<0.1 Pa (20 ° C) |
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| solubility |
very heavy in water (145 mg l −1 at 20 ° C) |
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| Refractive index |
1.4960 (20 ° C) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C | ||||||||||||||||||||||
Malathion is a dithiophosphoric acid ester that binds irreversibly to cholinesterase . Malathion is converted to the more toxic malaoxon in the body.
Extraction
Malathion can be produced by adding O , O- dimethyldithiophosphoric acid to diethyl maleate , which in turn is obtained from phosphorus (V) sulfide and methanol .
use
medicine
Malathion is still used in some European countries to treat head lice , pubic lice , clothing lice and scabies ; it kills both eggs (ovocidal) and living lice (pediculocidal). However, a Danish study found that the lice were mostly resistant to malathion and permethrin . In a French study, however, all lice were sensitive to malathion shampoo. In Germany and Switzerland, malathion products were withdrawn from the market due to their lack of acceptance.
Pest Control
In the 1980s, malathion was used in California to control the Mediterranean fruit fly . A mixture of malathion and corn syrup was sprayed weekly by helicopter over suburban communities in San Bernardino County , the latter being used as bait.
Malathion was used in many cities to fight the West Nile virus . From late 1999 to spring 2000, Long Island and the five boroughs of New York City were sprayed with malathion. The use of the insecticide is blamed for a large lobster death in Long Island Sound .
In Manitoba , a province in Canada, Winnipeg was sprayed in July 2005 as part of a West Nile virus fight. Malathion had already been used regularly in the summer months against annoying mosquitoes for decades. At that time, the owners had the opportunity to have their properties exempt from the spraying campaigns. Currently, Winnipeg is the only major city in Canada that has a malathion pest control program.
Malathion is also atomized together with diesel to combat mosquitoes on a large scale. By diluting the substance, it becomes weaker. If it is diluted too much, the mosquitoes may not be killed but develop resistances that make subsequent operations less effective.
Plant protection
Malathion is generally used against sucking insects in the cultivation of fruits, vegetables and ornamental plants as well as against fruit maggots .
Classification and regulation
Europe
The use of malathion in plant protection products is currently permitted in the EU until April 30, 2022. At national level it is approved in the Czech Republic, Italy and Spain, among others. In Austria, the approval expired at the end of April 2019 (use-by period until the end of October 2020). The permitted daily dose is 0.03 and the acute reference dose 0.3 milligrams per kilogram of body weight and day. In Germany and Switzerland, malathion is not approved as an active ingredient in plant protection products.
According to European legislation (Directive 98/8 / EC on the placing of biocidal products on the market ) and with the decision of August 14, 2007, a decision has been made not to include the active substance malathion in the corresponding list (Annex I / IA of Directive 98/8 / EG) for biocidal products. The sale of biocidal products that contain the active ingredient malathion is therefore no longer permitted in the EU and Switzerland, which has adopted this provision, for substances of product type 18 ( insecticides , acaricides and products against other arthropods ).
IARC
An assessment by the IARC in March 2015 concluded that there was limited evidence in humans of the carcinogenic potential of malathion, while the evidence would be sufficient that the substance leads to tumors in rats and mice. IARC therefore classifies malathion in category 2A (probably carcinogenic for humans, probably carcinogenic to humans ).
literature
- Brenner, GM (2000): Pharmacology. Philadelphia, PA: WB Saunders Company. ISBN 0-7216-7757-6
- Klaassen, CD (2001). Casarett & Doull's Toxicology McGraw-Hill Medical. ISBN 0-07-134721-6
Individual evidence
- ↑ a b c d e f g h i j k Entry on malathion in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
- ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-322.
- ↑ Entry on malathion in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
- ↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 121-75-5 or malathion ), accessed on November 2, 2015.
- ↑ Malathion data sheet at Sigma-Aldrich , accessed on May 12, 2017 ( PDF ).
- ^ Adrien Albert: The Selectivity of Drugs . Springer Science & Business Media, 2012, ISBN 978-94-009-5734-3 ( limited preview in Google Book Search [accessed October 2, 2019]).
- ↑ Patent US4367180 : Process for the preparation of malathion. Applicant: Rhone-Poulenc Agrochimie.
- ↑ Patent US3463841 : Malathion manufacture. Applicant: American Cyanmid.
- ↑ M. Kristensen, M. Knorr, AM Rasmussen, JB Jespersen: Survey of permethrin and malathion resistance in human head lice populations from Denmark. In: Journal of medical entomology. Volume 43, Number 3, May 2006, pp. 533-538, PMID 16739412 .
- ↑ S. Bouvresse, Z. Berdjane, R. Durand, J. Bouscaillou, A. Izri, O. Chosidow: Permethrin and malathion resistance in head lice: results of ex vivo and molecular assays. In: Journal of the American Academy of Dermatology. Volume 67, number 6, December 2012, pp. 1143-1150, doi : 10.1016 / j.jaad.2012.04.011 , PMID 22627039 .
- ↑ H. Stutzer: Head lice - Dealing with a resurgent parasitosis / A determination of the position using evidence-based criteria: Simple means . In: Deutsches Ärzteblatt 103, edition 9 of March 3, 2006, pages A-548, B-471, C-451.
- ↑ General Directorate Health and Food Safety of the European Commission: Entry on malathion in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on October 2, 2019.
- ↑ EU: Directive 98/8 / EC on the placing of biocidal products on the market (PDF) Official Journal of the European Communities - L 123/1 - April 24, 1998.
- ↑ EU: Decision 2007/565 on the non-inclusion of certain active substances in Annex I of Directive 98/8 / EC (PDF) Official Journal of the European Communities - L 216/17 - August 21, 2004.
- ^ IARC press release of March 20, 2015 IARC Monographs Volume 112: evaluation of five organophosphate inscecticides and herbicides , accessed on March 23, 2015.
