Ethiofencarb

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Structural formula
Structural formula of ethiofencarb
General
Surname Ethiofencarb
other names
  • 2- (ethylthiomethyl) phenyl-N-methylcarbamate
  • Croneton
Molecular formula C 11 H 15 NO 2 S
Brief description

colorless crystals

External identifiers / databases
CAS number 29973-13-5
EC number 249-981-9
ECHA InfoCard 100.045.423
PubChem 34766
ChemSpider 31991
Wikidata Q3591963
properties
Molar mass 225.31 g mol −1
Physical state

firmly

density

1.231 g cm −3

Melting point

33.4 ° C

boiling point

decomposes when heated

Vapor pressure

0.5 · 10 −3 Pa (20 ° C)

solubility
  • heavy in water (1.9 g l −1 at 20 ° C)
  • easily in dichloromethane and toluene (200 g l −1 at 20 ° C)
  • heavy in hexane (7.5 g l −1 at 20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 302-410
P: 273-501
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ethiofencarb is a synthetic insecticide from the active substance group of carbamates . It was introduced by Bayer in 1975 .

Extraction and presentation

Ethiofencarb can be obtained by reacting 2- (chloromethyl) phenol with ethanethiol and methyl isocyanate . Alternatively, the reaction of 2-ethylthiomethylphenol with phosgene and methylamine is also possible.

Mode of action

Ethiofencarb acts both as a contact poison and as a food poison. Its mode of action is comparable to all insecticides of the carbamate class. It inhibits the enzyme acetylcholine esterase in the synapses of the nervous system . As a result, the nerve transmission no longer functions properly, which paralyzes the muscles, especially the respiratory system, and can ultimately lead to death.

use

Ethiofencarb is mainly used against aphids. For example, it is used in fruit, vegetable and grain cultivation. The active ingredient is used in preparations as granules or emulsion for spraying and is sold under the name Croneton .

toxicology

The World Health Organization classifies ethiofencarb as a class Ib toxin (very dangerous). It gives an ADI value of 0.1 mg / kg. Ethiofencarb poisoning can cause symptoms such as muscle weakness , fasciculation , nausea and abdominal pain, as well as disorders of the central nervous system.

Ethiofencarb is toxic to fish and aquatic organisms, as well as to some plants. It is classified as environmentally hazardous. The compound has a high mobility in the soil, but is quickly broken down by oxidation to the sulfone and sulfoxide and by hydrolysis of the carbamate group to the corresponding phenols . Ethiofencarb is also susceptible to photo-oxidation . Liquid concentrates with 100 - 500 g / l are classified as dangerous to bees (B1) , while ten percent granules are classified as B4 (not dangerous to bees).

Analytics

The reliable detection and quantification of Ethiofencarb can be carried out using liquid chromatographic methods. A mass spectrometer can be used for identification after the chromatographic separation .

Admission

Ethiofencarb is no longer approved in the European Union . The maximum residue level in all foods is 0.01 mg / kg. The active ingredient has been approved in India .

Individual evidence

  1. ↑ a b c d Entry on Ethiofencarb. In: Römpp Online . Georg Thieme Verlag, accessed on June 19, 2018.
  2. ↑ a b c d e f g Entry on Ethiofencarb in the GESTIS substance database of the IFA , accessed on July 10, 2018 (JavaScript required)
  3. ↑ a b c d Entry on Ethiofencarb in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 11, 2018.
  4. ↑ Entry on Ethiofencarb in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on July 10, 2018. Manufacturers or distributors can expand the harmonized classification and labeling .
  5. ↑ Data sheet Ethiofencarb from Sigma-Aldrich , accessed on July 11, 2018 ( PDF ).
  6. ↑ Thomas A. Unger: Pesticide synthesis handbook . Noyes Publications, 1996, ISBN 978-0-8155-1401-5 , pp. 85 ( limited preview in Google Book search).
  7. ↑ a b c d e f Paranjape, Kalyani .: The pesticide encyclopedia . CABI, Wallingford, Oxfordshire UK 2014, ISBN 978-1-78064-014-3 ( limited preview in Google Book Search).
  8. ↑ International Program on Chemical Safety., Inter-Organization Program for the Sound Management of Chemicals., World Health Organization .: WHO recommended classification of pesticides by hazard and guidelines to classification 2009. World Health Organization, Geneva 2010, ISBN 92-4154796- 0 ( who.int [PDF]).
  9. ↑ WHO | World Health Organization: WHO | Inventory of evaluations performed by the Joint Meeting on Pesticide Residues (JMPR). Retrieved July 12, 2018 .
  10. ↑ Gudrun head Wolfgang Schwack: photo degradation of the carbamate insecticide ethiofencarb . In: Pesticide Science . tape 43 , no. 4 , April 1995, pp. 303-309 , doi : 10.1002 / ps.2780430409 .
  11. ↑ Springer Environmental Lexicon . 2nd Edition. Springer Berlin Heidelberg, Berlin, Heidelberg 2000, ISBN 978-3-642-56998-2 ( limited preview in Google book search [accessed September 13, 2018]).
  12. ↑ Derick Lucas: Optimizing Sample Preparation for LC / MS / MS of Pesticide Residues in Herbal Teas. In: Agilent Technologies, Inc. December 17, 2013, accessed June 28, 2018 .
  13. ↑ Directorate-General for Health and Food Safety of the European Commission: Entry on ethiofencarb in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on May 19, 2018.