Flufenacet

Structural formula
General
Surname	Flufenacet
other names	N - (4-Fluorophenyl) - N -isopropyl-2- (5-trifluoromethyl- (1,3,4) -thiadiazol-2-yloxy) acetamide
Molecular formula	C 14 H 13 F 4 N 3 O 2 S
Brief description	beige solid
External identifiers / databases
EC number	604-290-5
ECHA InfoCard	100.127.787
PubChem	86429
Wikidata	Q1430589
properties
Molar mass	363.33 g mol −1
Physical state	firmly
density	1.31 g cm −3
Melting point	79 ° C
boiling point	150 ° C (decomposition)
solubility	practically insoluble in water (56 mg l −1 at 20 ° C); soluble in acetone , acetonitrile and dichloromethane ;
safety instructions
H and P phrases	H: 302-317-373-410
	P: 273-280-301 + 312 + 330-302 + 352-314
Toxicological data	589 mg kg −1 ( LD 50 , female rat , oral ) ; 1617 mg kg −1 ( LD 50 , male rat , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Flufenacet is an active ingredient for crop protection and a chemical compound from the group of oxyacetamides and thiadiazoles .

Extraction and presentation

Flufenacet, by reaction of equivalent amounts of 2-methylsulfonyl-5-trifluoromethyl-1,3,4-thiadiazole with 2-hydroxy- [ N - (4-fluorophenyl) - N -isopropyl] -acetamide in the presence of sodium hydroxide in acetone are recovered .

properties

Flufenacet is a yellowish solid that is practically insoluble in water.

use

Flufenacet is used as an active ingredient in pesticides ( pre-emergence herbicide ) in arable, vegetable, fruit and ornamental crops growing.

The compound shows a strong effect on meristematic tissues, interferes with membrane functions and changes the permeability of cell membranes. It acts as an inhibitor of the interaction between the thyroid hormone receptor and steroid receptor co-regulator 2.

Admission

Flufenacet was provisionally included in Annex I of the Plant Protection Products Directive 91/414 / EEC until December 31, 2013. In Germany, Austria and Switzerland it is contained as an active ingredient in approved plant protection products.

Environmental impact

The breakdown product trifluoroacetate (TFA) can be detected in the groundwater and is difficult to separate during drinking water treatment.

Trade names

Sunfire, Cadou, Bacara

Web links

EPA factsheet: Flufenacet

Individual evidence

↑ ^a ^b ^c ^d ^e Entry on Flufenacet in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ ^a ^b ^c LAWA expert group "Substances": Substance data sheet: Flufenacet (PDF; 65 kB), as of March 15, 2010.
↑ ^a ^b ^c Flufenacet (PDF; 92 kB).
↑ Entry on N- (4-fluorophenyl) -N-isopropyl-2- (5-trifluoromethyl- [1,3,4] thiadiazol-2-yloxy) acetamide Template: Linktext-Check / Escaped in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can extend the harmonized classification and labeling .
↑ ^a ^b Entry on Flufenacet. In: Römpp Online . Georg Thieme Verlag, accessed on January 4, 2020.
↑ Hatzios KK, ed; Herbicide Handbook of the Weed Science Society of America. 7th ed. Suppl. Champaign, IL: Weed Sci Soc Amer p. 9 (1998).
↑ General Directorate Health and Food Safety of the European Commission: Entry on Flufenacet (formerly fluthiamide) in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.

↑ Federal Environment Agency (UBA): Press release No. 38/2019 of October 21, 2019. Retrieved January 5, 2020 .

[GESTIS-1] Entry on Flufenacet in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[LAWA-2] LAWA expert group "Substances": Substance data sheet: Flufenacet (PDF; 65 kB), as of March 15, 2010.

[EU-3] Flufenacet (PDF; 92 kB).

[CLP_100.127.787-4] Entry on N- (4-fluorophenyl) -N-isopropyl-2- (5-trifluoromethyl- [1,3,4] thiadiazol-2-yloxy) acetamide Template: Linktext-Check / Escaped in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can extend the harmonized classification and labeling .

[Römpp-5] Entry on Flufenacet. In: Römpp Online . Georg Thieme Verlag, accessed on January 4, 2020.

[toxnet-6] Hatzios KK, ed; Herbicide Handbook of the Weed Science Society of America. 7th ed. Suppl. Champaign, IL: Weed Sci Soc Amer p. 9 (1998).

[PSM-7] General Directorate Health and Food Safety of the European Commission: Entry on Flufenacet (formerly fluthiamide) in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.

[UBA-8] Federal Environment Agency (UBA): Press release No. 38/2019 of October 21, 2019. Retrieved January 5, 2020 .