Metaflumizone

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Structural formula
Structure of metaflumizone
( E ) isomer
General
Non-proprietary name Metaflumizone
other names

( EZ ) -2 '- [2- (4-cyanophenyl) -1- (α, α, α-trifluoro- m -tolyl) ethylidene] -4- (trifluoromethoxy) carbanilohydrazide

Molecular formula C 24 H 16 F 6 N 4 O 2
External identifiers / databases
CAS number 139968-49-3
EC number 604-167-6
ECHA InfoCard 100.107.480
PubChem 20056430
ChemSpider 16738643
Wikidata Q6822502
Drug information
ATC code

Q P53AX25

Drug class

insecticide

Mechanism of action

Sodium channel antagonist

properties
Molar mass 506.40 g · mol -1
Melting point
  • 133 ° C [( E ) -isomer]
  • 188 ° C [( Z ) -isomer]
Vapor pressure
  • 7.94 · 10 −10 Pa (° C) [( E ) -isomer]
  • 2.42 · 10 −7 Pa (° C) [( Z ) -isomer]
solubility
  • 1.81 µg · l −1 (20 ° C) pH 7 in water
  • 153 g l −1 (20 ° C) in acetone
  • 99 g l −1 (20 ° C) in dichloromethane
  • 4 g l −1 (20 ° C) in toluene
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
09 - Dangerous for the environment

Caution

H and P phrases H: 400
P: 273
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Metaflumizon is an insecticide from the semicarbazone group . The compound is a sodium channel - antagonist that affects the conduction of insects and thus leads to paralysis and death of insects.

Isomerism

There are two isomers of the active ingredient, the ( E ) isomer and the ( Z ) isomer. In technical metaflumizone, the isomer ratio ( E ) :( Z ) is about 9: 1.

Approval and trade names

Metaflumizon was approved as an ectoparasitic for dogs and cats in Germany . It was marketed as a monopreparation for cats under the trade name ProMeris , but has not been marketable since June 30, 2018. The same applies to the former combination preparation with Amitraz called ProMeris Duo .

In a number of EU countries, including Austria, but not in Germany and Switzerland, plant protection products with this active ingredient are permitted (trade name Alverde ).

Web links

Individual evidence

  1. a b c d e f g h i Metaflumizone data sheet at the Federal Office for Consumer Protection and Food Safety , accessed on May 14, 2017.
  2. a b Metaflumizone data sheet from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).
  3. General Directorate Health and Food Safety of the European Commission: Entry on metaflumizone in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 25, 2016.