Acrinathrin

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Structural formula
Structural formula of acrinathrin
General
Surname Acrinathrin
other names

( S ) -Cyano (3-phenoxyphenyl) methyl- ( Z ) - (1 R , 3 S ) -2,2-dimethyl [2- (2,2,2-trifluoro-1-trifluoromethylethoxycarbonyl) vinyl] -cyclopropanecarboxylate

Molecular formula C 26 H 21 F 6 NO 5
Brief description

white to beige powder

External identifiers / databases
CAS number
  • 101007-06-1
  • 103833-18-7 (R isomer)
EC number 600-147-6
ECHA InfoCard 100.126.096
PubChem 6436606
Wikidata Q342726
properties
Molar mass 541.44 g mol −1
Physical state

firmly

Melting point

81 ° C

boiling point

230 ° C (decomposition)

Vapor pressure

4.40 · 10 −5 mPa (25 ° C)

solubility
  • practically insoluble in water (0.002 mg l −1 at 20 ° C)
  • soluble in xylene and acetone
safety instructions
GHS labeling of hazardous substances
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 332-410
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 .

Acrinathrin is a chemical compound from the group of pyrethroid esters .

Extraction and presentation

Acrinathrin can be obtained by a multi-stage reaction starting from 2-trifluoro-1-trifluoromethylethyldichloroacetate with triphenylphosphine , ammonia , chrysanthemum acid , ozone and m- phenoxycyanobenzyl alcohol .

properties

Acrinathrin is a white to yellowish solid that is practically insoluble in water. Its chemical structure is similar to cypermethrin , with its chlorine atoms being replaced by a polyfluorinated ester group . The compound was discovered in the 1980s by Roussel Uclaf and synthesized for the first time. It is stable under acidic conditions, but unstable under diffuse light and alkaline conditions.

use

Acrinathrin is used as an insecticide and acaricide against a number of herbivorous mites .

Admission

In the EU, on January 1, 2012, the use as an insecticide and as an acaricide was approved in quantities of a maximum of 22.5 g / ha per application. For plant protection products currently on the market that contain acrinathrin and do not comply with the regulations, the approval will be changed or revoked, if necessary, by December 31, 2015 at the latest.

In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

Individual evidence

  1. ↑ a b c d e f g h i j k Entry on acrinathrin in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.
  2. ↑ a b Data sheet acrinathrin from Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).
  3. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 929 ( limited preview in Google Book search).
  4. ↑ Allain Tressaud: Fluorine and the Environment: Agrochemicals, Archeology, Green Chemistry ... Elsevier, 2006, ISBN 0-444-52672-2 , p. 147 ( limited preview in Google Book search).
  5. ↑ Summary of Toxicological Studies on Acrinathrin. (PDF) Retrieved March 20, 2019 (English).
  6. ↑ Implementing Regulation (EU) No. 974/2011 (PDF) of the Commission of 29 September 2011 on the approval of the active ingredient acrinathrin in accordance with Regulation (EC) No. 1107/2009 of the European Parliament and of the Council on the placing of plant protection products on the market and amending it of the Annex of the Commission Implementing Regulation (EU) No. 540/2011 and Commission Decision 2008/934 / EC
  7. ↑ General Directorate Health and Food Safety of the European Commission: Entry on acrinathrin in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 12, 2016.