Fonofos
| Structural formula | |||||||||||||||||||
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| Simplified structural formula without stereochemistry | |||||||||||||||||||
| General | |||||||||||||||||||
| Surname | Fonofos | ||||||||||||||||||
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| Molecular formula | C 10 H 15 OPS 2 | ||||||||||||||||||
| Brief description |
colorless to yellow liquid with an aromatic odor |
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| properties | |||||||||||||||||||
| Molar mass | 246.32 g · mol -1 | ||||||||||||||||||
| Physical state |
liquid |
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| density |
1.17 g · cm -3 |
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| boiling point |
130 ° C |
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| Vapor pressure |
27 mPa (at 20 ° C) |
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| solubility |
practically insoluble in water (13 mg l −1 at 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 . | |||||||||||||||||||
Fonofos is a synthetic insecticide from the active ingredient group of phosphoric acid esters .
It was first described in 1965.
Extraction and presentation
Fonofos can be obtained through a multi-stage reaction. For this purpose, chloroethane and phosphorus trichloride are catalysed by aluminum chloride and converted to ethylthiophosphonyl chloride, which is then reacted with sodium ethoxide . The resulting molecule then reacts with thiophenol to form fonofos.
Structure and mode of operation
Fonofos is chiral, it consists of a 1: 1 mixture of the two enantiomers : the ( R ) isomer is more biologically active than the ( S ) isomer.
Like all organophosphates and phosphoric acid esters, the action of Fonofos is based on the irreversible inhibition of acetylcholine esterase in nerve cells. This has the effect that the transmission of stimuli in the nervous system is disturbed or comes to a standstill, which in turn can lead to paralysis, respiratory failure and ultimately death.
Areas of application
Fonofos is a soil insecticide with a broad spectrum of activity. It is used as a granulate or emulsifiable concentrate and acts as a contact poison and food poison. It is mainly used against flies and worms in grain, fruit and vegetable cultivation.
toxicology
Fonofos is classified as highly toxic by the American EPA . The symptoms of poisoning are similar to those of other phosphoric acid esters , but with Fonofos these occur even at lower doses. Poisoning can occur through both oral and dermal ingestion. Symptoms of poisoning with Fonofos can also occur after a delay of up to twelve hours after ingestion. Symptoms include initially blurred vision, headache, and dizziness. Eye contact can cause sweating and muscle twitching, while poisoning by swallowing can manifest itself in nausea, stomach cramps and diarrhea.
Ecotoxicology
Fonofos is highly toxic to birds, fish and aquatic invertebrates. It is also poisonous to bees. It is moderately persistent in the soil with a half-life of 40 days. In water, it degrades quickly through hydrolysis .
Analytics
Both liquid and gas chromatographic methods can be used for reliable detection and quantification of Fonofos . A mass spectrometer can be used for identification after the chromatographic separation .
Admission
Fonofos is not approved in the states of the European Union or in Switzerland. The maximum residue level was set at 0.01 mg / kg for all foods.
Individual evidence
- ↑ a b c d e Entry on Fonofos in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 29, 2018.
- ^ CDC - NIOSH Pocket Guide to Chemical Hazards - Fonofos. Retrieved September 17, 2018 (American English).
- ↑ a b c d Entry on Fonophos in the GESTIS substance database of the IFA , accessed on August 29, 2018 (JavaScript required)
- ↑ Entry on Fonophos in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 29, 2018. Manufacturers or distributors can expand the harmonized classification and labeling .
- ↑ Thomas A. Unger: Pesticide synthesis handbook . Noyes Publications, 1996, ISBN 978-0-8155-1401-5 , pp. 85 ( limited preview in Google Book search).
- ↑ a b Paranjape, Kalyani .: The pesticide encyclopedia . CABI, Wallingford, Oxfordshire UK 2014, ISBN 978-1-78064-014-3 ( limited preview in Google Book Search).
- ↑ Smith, Gregory James .: Toxicology & pesticide use in relation to wildlife: organophosphorus & carbamate compounds . CK Smoley, [United States] 1993, ISBN 0-8493-8721-3 ( limited preview in Google Book Search [accessed September 18, 2018]).
- ↑ a b Kamrin, Michael A .: Pesticide profiles: toxicity, environmental impact, and fate . CRC / Lewis Publishers, Boca Raton, FL 1997, ISBN 978-1-4200-4922-0 ( limited preview in Google Book Search [accessed September 17, 2018]).
- ↑ A. Moreno López, L. Moreno López, JL Pineda Lucas, Joan Stevens: Multiresidue Analysis of Pesticides in Olive Samples Using GC / MS / MS. (pdf) In: agilent.com. June 18, 2014, accessed September 18, 2018 .
- ↑ Multiresidue Analysis of 301 Pesticides in Food Samples by LC / Triple Quadrupole Mass Spectrometry - Food Safety Magazine. Retrieved September 18, 2018 .
- ↑ General Directorate Health and Food Safety of the European Commission: Entry on Fonofos in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on August 29, 2018.