Tetramethrin

Structural formula
	Mixture of stereoisomers
General
Surname	Tetramethrin
other names	[(1,3-dioxo-1,3,4,5,6,7-hexahydro-2 H -isoindol-2-yl) methyl] -2,2-dimethyl-3- (2-methylprop-1-enyl ) cyclopropanecarboxylate; Neopynamine; Neo-pynamine; Phthalhrin;
Molecular formula	C 19 H 25 NO 4
Brief description	colorless crystals or powder with a faint odor; in technical quality: pale yellow-brownish solid;
External identifiers / databases
EC number	231-711-6
ECHA InfoCard	100,028,829
PubChem	83975
Wikidata	Q3234577
Drug information
ATC code	P03 BA04 ; Q P53AC13 ;
properties
Molar mass	331.41 g mol −1
Physical state	firmly
density	1.108 g cm −3
Melting point	68-70 ° C
boiling point	455 ° C
solubility	almost insoluble in water (1.83 mg l −1 at 20 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 302-351-371-410
	P: ?
Toxicological data	4640 mg kg −1 ( LD 50 , rat , oral ) ; > 2500 mg kg −1 ( LD 50 , rabbit , transdermal ) ; 0.019 mg kg −1 ( LC 50 , fish , 96 h , median value) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tetramethrin is a chemical compound from the group of pyrethroids .

history

Tetramethrin was the second commercially available pyrethroid. It was introduced by Sumitomo Chemical in 1965 as a non-systemic contact insecticide. Tetramethrin was approved as an insecticide in Germany from 1977 to 1981 .

Extraction and presentation

Tetramethrin can be prepared from 1-cyclohexene-1,2-dicarboximide and reaction with formaldehyde to form the hemiaminal and subsequent esterification with chrysanthemoyl chloride.

A mixture is used under the name d-tetramethrin which is enriched with the (1 R ) - cis - and (1 R ) - trans isomers.

use

Tetramethrin is mainly used against indoor hygiene pests such as flies, mosquitoes and cockroaches.

Admission

The use of the active ingredient tetramethrin in plant protection products is not permitted in the European Union. In Germany, Austria and Switzerland, no pesticides with this active ingredient are currently approved. Until November 2005, tetramethrin was included in the Swiss Plant Protection Product Ordinance in Appendix 1 (Active ingredients approved for use in plant protection products). With regard to the notification as biocide , product type 18 (insecticides, acaricides and products against other arthropods), the decision is still pending.

Dismantling

Tetramethrin degrades rapidly in the environment. The photolysis - half-life in the air by a reaction with ozone is around half an hour. The hydrolysis half-life is pH- dependent and ranges from a few minutes to three weeks.

Trade names

Blattanex Fly Spray , Blattanex Wasp foam , Blattanex Wasp Power Spray , Detia Garda vermin spray , Dr. Stähler Power Spray 4 M, Varena insect spray

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on tetramethrin in the GESTIS substance database of the IFA , accessed on December 31, 2019(JavaScript required) .
↑ ^a ^b ^c ^d Entry on tetramethrin. In: Römpp Online . Georg Thieme Verlag, accessed on June 11, 2014.
↑ Entry on tetramethrin in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on November 10, 2013.
↑ Entry on tetramethrin in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 31, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ approval history of the BVL
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 960 ( limited preview in Google Book search).
↑ Regulation (EC) No. 2076/2002 of the Commission of November 20, 2002 (PDF) extending the deadline according to Article 8 (2) of Council Directive 91/414 / EEC and on the non-inclusion of certain active substances in Annex I of this Directive and the revocation of the approval of plant protection products with these active substances.
↑ General Directorate Health and Food Safety of the European Commission: Entry on tetramethrin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 18, 2016.
↑ Ordinance on the placing of plant protection products on the market (Plant Protection Products Ordinance, PSMV); Change from November 7, 2005
↑ Consolidated list of notified active ingredients ( Memento of the original from August 26, 2016 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. , 2014 @1@ 2

↑ Half-life at pH≈9: approx. 13 - 20 minutes; pH≈7: approx. 21.5 - 26 hours; pH≈5: approx. 16 - 20 days
Reregistration Eligibility Decision (RED) for Tetramethrin. (PDF) EPO , June 23, 2008, p. 19 , archived from the original on October 16, 2014 ; accessed on April 21, 2020 (English).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on tetramethrin in the GESTIS substance database of the IFA , accessed on December 31, 2019(JavaScript required) .

[roempp-2] Entry on tetramethrin. In: Römpp Online . Georg Thieme Verlag, accessed on June 11, 2014.

[PPDB-3] Entry on tetramethrin in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on November 10, 2013.

[CLP_100.028.829-4] Entry on tetramethrin in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 31, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .

[5] roval history of the BVL

[unger-6] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 960 ( limited preview in Google Book search).

[7] Regulation (EC) No. 2076/2002 of the Commission of November 20, 2002 (PDF) extending the deadline according to Article 8 (2) of Council Directive 91/414 / EEC and on the non-inclusion of certain active substances in Annex I of this Directive and the revocation of the approval of plant protection products with these active substances.

[PSM-8] General Directorate Health and Food Safety of the European Commission: Entry on tetramethrin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 18, 2016.

[9] Ordinance on the placing of plant protection products on the market (Plant Protection Products Ordinance, PSMV); Change from November 7, 2005

[10] Consolidated list of notified active ingredients ( Memento of the original from August 26, 2016 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. , 2014 @1@ 2

[11] Half-life at pH≈9: approx. 13 - 20 minutes; pH≈7: approx. 21.5 - 26 hours; pH≈5: approx. 16 - 20 days
Reregistration Eligibility Decision (RED) for Tetramethrin. (PDF) EPO , June 23, 2008, p. 19 , archived from the original on October 16, 2014 ; accessed on April 21, 2020 (English).