Flumetralin

Structural formula
General
Surname	Flumetralin
other names	N - (2-chloro-6-fluorobenzyl) - N -ethyl-2,6-dinitro-4- (trifluoromethyl) aniline ( IUPAC ) ; N - (2-chloro-6-fluorobenzyl) - N -ethyl-α, α, α-trifluoro-2,6-dinitro- p -toluidine; CGA 41065;
Molecular formula	C 16 H 12 ClF 4 N 3 O 4
Brief description	yellow crystals
External identifiers / databases
EC number	613-108-3
ECHA InfoCard	100.120.402
PubChem	62210
ChemSpider	56023
Wikidata	Q22807596
properties
Molar mass	421.73 g mol −1
Physical state	firmly
density	1.54 g cm −3
Melting point	104.6 ° C
boiling point	decomposes at 195 ° C
Vapor pressure	0.720 · 10 −3 Pa (20 ° C)
solubility	practically insoluble in water (0.00001 g l −1 at 20 ° C); slightly in acetone 560 g l −1 at 20 ° C); slightly in toluene 400 g l −1 at 20 ° C); little in ethanol 18 g l −1 at 20 ° C); little in n -hexane 14 g l −1 at 20 ° C);
safety instructions
H and P phrases	H: 315-317-319-410
	P: 261-264-273-280-333 + 313-391
Toxicological data	3100 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 mg kg −1 ( LD 50 , rat , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Flumetralin is a synthetic growth regulator . It was developed in 1983.

presentation

4-chlorobenzotrifluoride is nitrated and then reacted with ethyl (2-chloro-6-fluorobenzyl) amine to form flumetralin.

properties

Flumetralin is a yellow, crystalline solid that is insoluble in water. The substance is odorless. It is stable at pH values between 5 and 9 and decomposes exothermically at temperatures above 250 ° C.

Use and mode of action

Flumetralin is used in tobacco growing to control axillary bud growth after the flowers have been cut. It has a local systemic effect as well as a contact effect. Due to its high persistence, an effect over a long period is possible.

toxicology

According to the WHO , there is no risk of flumetralin with normal use. It is not very toxic to mammals , birds and bees , but very toxic to aquatic life such as fish and shellfish . In addition, flumetralin is very persistent with a half-life in the laboratory of 727 days (at 20 ° C). It is only slightly sensitive to hydrolysis in water , but degrades quickly when exposed to sunlight.

Analytics

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

Admission

Flumetralin has been approved in the European Union since December 11, 2015. Approval is limited to December 11, 2022. In the EU, the maximum residue limit in all foods is 0.01 mg / kg.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on Flumetralin in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on January 30, 2019.

↑ ^a ^b ^c Entry on flumetralin in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

↑ Entry on Flumetralin in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 30, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .

↑ Flumetralin data sheet at Sigma-Aldrich , accessed on January 30, 2019 ( PDF ).

↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 868 ( limited preview in Google Book search).

↑ ^a ^b ^c Paranjape, Kalyani .: The pesticide encyclopedia . CABI, Wallingford, Oxfordshire UK 2014, ISBN 978-1-78064-014-3 , pp. 212 ( limited preview in Google Book search).

↑ Vivian Xianyu Chen, Andy Zhai: Analysis of Multipesticide Residues in Tobacco. (PDF) Agilent Technologies, Inc., April 29, 2016, accessed January 30, 2019 .

↑ Susan Strange Herrmann, Mette Erecius Poulsen: Validation Report 23 B - Determination of pesticide residues in wheat, rye, oat and rice by LC-MS / MS and GC-MS / MS. (PDF) In: EURL for Cereals and Feeding stuff. January 2018, accessed January 30, 2019 .

↑ Directorate-General for Health and Food Safety of the European Commission: Entry on Flumetralin in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on January 30, 2019.

[PPDB-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on Flumetralin in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on January 30, 2019.

[GESTIS-2] Entry on flumetralin in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[CLP_100.120.402-3] Entry on Flumetralin in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 30, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .