Fenamiphos

Structural formula
	1: 1 mixture (racemate) of ( R ) form (left) and ( S ) form (right)
General
Surname	Fenamiphos
other names	Phenamiphos; ( RS ) -Ethyl-4-methylthio- m -tolyl isopropyl phosphoramidate;
Molecular formula	C 13 H 22 NO 3 PS
Brief description	colorless solid
External identifiers / databases
EC number	244-848-1
ECHA InfoCard	100.040.756
PubChem	31070
Wikidata	Q32693
properties
Molar mass	303.36 g mol −1
Physical state	firmly
density	1.191 g cm −3 (23 ° C)
Melting point	49.3 ° C
boiling point	150 ° C (decomposition)
Vapor pressure	0.12 mPa (20 ° C)
solubility	slightly soluble in water (0.4 g l −1 at 20 ° C); soluble in dichloromethane, isopropanol and toluene;
safety instructions
H and P phrases	H: 300-310-330-319-410
	P: 260-280-301 + 310 + 330-302 + 352 + 310-304 + 340 + 310-403 + 233
MAK	Switzerland: 0.1 mg m −3 (measured as inhalable dust )
Toxicological data	8 mg kg −1 ( LD 50 , rat , oral ) ; 178 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fenamiphos is a 1: 1 mixture (racemate) of two chemical compounds from the group of phosphoramidates .

Extraction and presentation

Fenamiphos can be obtained by reacting phosphorus oxychloride with ethanol , 3-methyl-4-thiomethylphenol and isopropylamine .

properties

Fenamiphos is a solid that is sparingly soluble in water. Compared to other organophosphorus compounds, it is relatively stable to hydrolysis . Its sulfoxide, sulfone and the desisopropylated sulfone metabolite are just as toxic as the compound itself. The two enantiomers have different effects.

use

Fenamiphos is as active ingredient in pesticides used. It was first approved in the USA in 1972, is used as a nematicide in a number of crops and works by inhibiting acetylcholinesterase . The connection came into the news because the Brandenburg food control system measured increased residues of the active ingredient in cucumbers in November 2011 and informed the food authorities in Europe about this via the European rapid alert system. Fenamiphos was produced by Bayer AG under the trade name Nemacur for the world market, at the end of 2010 this product line was sold to AMVAC Chemical Corporation.

Admission

In the European Union, Fenamiphos was approved with effect from August 1, 2007 for "applications as a nematicide via drip irrigation in greenhouses with a permanent structure".

In Germany, Austria and Switzerland no pesticides with this active ingredient are approved, but for example in Spain, Portugal, Italy or Hungary.

Web links

EU: Review report for the active substance fenamiphos - Finalized in the Standing Committee on the Food Chain and Animal Health at its meeting on July 14, 2006 (PDF; 72 kB)

Individual evidence

↑ ^a ^b ^c Entry on Fenamiphos at Extoxnet.
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on Fenamiphos in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ Entry on Fenamiphos in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Fenamiphos data sheet , PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 22224-92-6 or Fenamiphos ), accessed on November 2, 2015.
↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 306 ( limited preview in Google Book search).
^ ^A ^b Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 , pp. 309 ( limited preview in Google Book search).
↑ ^a ^b Interim Reregistration Eligibility Decision (IRED) Fenamiphos (PDF; 450 kB), May 2002.
↑ Yei-Shung Wang, Kok-Thong Tai, Jui-Hung Yen: Separation, bioactivity, and dissipation of enantiomers of the organophosphorus insecticide fenamiphos. In: Ecotoxicology and Environmental Safety . 57, 2004, pp. 346-353, doi : 10.1016 / j.ecoenv.2003.08.012 .
↑ Federal Institute for Risk Assessment: Measured residues of the pesticide Fenamiphos on cucumbers are a health risk for children - BfR Opinion No. 050/2011 of November 8, 2011 (PDF; 55 kB).
↑ Bloomberg Businessweek: Company Overview of Bayer CropScience LLC, Ethoprophos And Fenamiphos Product Lines , accessed November 12, 2012.
↑ Directive 2006/85 / EC of the Commission of October 23, 2006 amending Council Directive 91/414 / EEC to include the active substances Fenamiphos and Ethephon (PDF) .
↑ General Directorate Health and Food Safety of the European Commission: Entry on Fenamiphos (aka phenamiphos) in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.

[Extoxnet-1] Entry on Fenamiphos at Extoxnet.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on Fenamiphos in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[CLP_100.040.756-3] Entry on Fenamiphos in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[Sigma-4] Fenamiphos data sheet , PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).

[5] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 22224-92-6 or Fenamiphos ), accessed on November 2, 2015.

[Unger-6] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 306 ( limited preview in Google Book search).

[Roberts-7] A ^b Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 , pp. 309 ( limited preview in Google Book search).

[EPA-8] Interim Reregistration Eligibility Decision (IRED) Fenamiphos (PDF; 450 kB), May 2002.

[DOI10.1016/j.ecoenv.2003.08.012-9] Yei-Shung Wang, Kok-Thong Tai, Jui-Hung Yen: Separation, bioactivity, and dissipation of enantiomers of the organophosphorus insecticide fenamiphos. In: Ecotoxicology and Environmental Safety . 57, 2004, pp. 346-353, doi : 10.1016 / j.ecoenv.2003.08.012 .

[10] Federal Institute for Risk Assessment: Measured residues of the pesticide Fenamiphos on cucumbers are a health risk for children - BfR Opinion No. 050/2011 of November 8, 2011 (PDF; 55 kB).

[11] Bloomberg Businessweek: Company Overview of Bayer CropScience LLC, Ethoprophos And Fenamiphos Product Lines , accessed November 12, 2012.

[12] Directive 2006/85 / EC of the Commission of October 23, 2006 amending Council Directive 91/414 / EEC to include the active substances Fenamiphos and Ethephon (PDF) .

[PSM-13] General Directorate Health and Food Safety of the European Commission: Entry on Fenamiphos (aka phenamiphos) in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.