Tolylfluanid

Structural formula
General
Surname	Tolylfluanid
other names	N - [dichloro (fluoro) methyl] sulfanyl- N - (dimethylsulfamoyl) -4-methylaniline ( IUPAC ) ; 1,1-dichloro- N - ((dimethylamino) sulfonyl) -1-fluoro- N - (4-methylphenyl) methanesulfenamide; Dichloro- N - ((dimethylamino) sulfonyl) fluoro- N - ( p -tolyl) methanesulfenamide; Euparen M;
Molecular formula	C 10 H 13 Cl 2 FN 2 O 2 S 2
Brief description	white, almost odorless powder
External identifiers / databases
EC number	211-986-9
ECHA InfoCard	100,010,898
PubChem	12898
ChemSpider	12364
Wikidata	Q423824
properties
Molar mass	347.2 g mol −1
Physical state	firmly
density	1.52 g cm −3
Melting point	96 ° C
boiling point	from 150 ° C decomposition
Vapor pressure	0.2 mPa (20 ° C)
solubility	very heavy in water (0.9 mg l −1 at 20 ° C)
safety instructions
H and P phrases	H: 330-315-317-319-335-372-400
	P: 273-280-302 + 352-304 + 340 + 310-305 + 351 + 338-314
Toxicological data	1000 mg kg −1 ( LD 50 , rat , oral ) ; 500 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 .

Tolylfluanid is an organic chemical compound that is an active ingredient in fungicides and wood preservatives .

Extraction and presentation

The synthesis of tolylfluanid begins with the reaction of dimethylamine and sulfuryl chloride . The product reacts further with p -toludine and with dichlorofluoromethanesulfenyl chloride to form the end product.

Absorption, metabolism and excretion

Tolylfluanid is irritating to the respiratory tract, gastrointestinal tract, eyes and skin.

Tolylfluanid is rapidly and almost completely absorbed from the gastrointestinal tract. The highest concentrations are found in the blood, lungs, liver, kidneys, spleen and thyroid gland. 99% is excreted in the urine within two days. However, there is some accumulation in the thyroid.

Environmental behavior

Tolylfluanid hydrolyzes slowly in the acidic range. The half-life is shorter when the pH is high; at pH = 7 it is over 2 days. In an aerobic environment (pH = 7.7–8.0), tolylfluanid decomposes hydrolytically and microbially to N , N -dimethyl- N '- (4-methylphenyl) sulfamide (DMST) and dimethyl sulfamide . After 14 days, tolylfluanid is basically broken down. The half-life of DMST is 50-70 days.

use

The active ingredient is used in fruit and ornamental plant cultivation against gray mold rot ( botrytis ), against late blight and brown rot on tomatoes and against powdery mildew in cucumbers . A waiting period of three days must then be observed for the vegetables.

Admission

In the EU countries such as Germany and Austria as well as in Switzerland, tolylfluanid is not contained in any approved pesticides.

Web links

EPA factsheet
fluoridealert.org: Tolyfluanid

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on tolylfluanid (content of particles with an aerodynamic diameter less than 50 µm> = 0.1% by weight) in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ Entry on Tolylfluanid in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on March 7, 2014.
↑ Entry on Dichloro-N - [(dimethylamino) sulphonyl] fluoro-N- (p-tolyl) methanesulphenamide 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 use the harmonized classification and expand labeling .
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 985 ( preview ).
↑ ^a ^b Svensk chemical inspection: Tolylfluanid ( Memento from September 27, 2007 in the Internet Archive ) (PDF file; 50 kB).
↑ General Directorate Health and Food Safety of the European Commission: Entry on tolylfluanid in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved March 3, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on tolylfluanid (content of particles with an aerodynamic diameter less than 50 µm> = 0.1% by weight) in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[ppdb-2] Entry on Tolylfluanid in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on March 7, 2014.

[CLP_100.010.898-3] Entry on Dichloro-N - [(dimethylamino) sulphonyl] fluoro-N- (p-tolyl) methanesulphenamide 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 use the harmonized classification and expand labeling .

[unger-4] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 985 ( preview ).

[kemi-5] Svensk chemical inspection: Tolylfluanid ( Memento from September 27, 2007 in the Internet Archive ) (PDF file; 50 kB).

[PSM-6] General Directorate Health and Food Safety of the European Commission: Entry on tolylfluanid in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved March 3, 2016.