Fluthiacet-methyl

Structural formula
	Mixture of ( E ) and ( Z ) isomers, only the ( Z ) isomer is shown
General
Surname	Fluthiacet-methyl
other names	Methyl {2-chloro-4-fluoro-5 - [( EZ ) -5,6,7,8-tetrahydro-3-oxo-1 H , 3 H - [1,3,4] thiadiazole [3,4- a ] pyridazin-1-ylideneamino] phenylthio} acetate
Molecular formula	C 15 H 15 ClFN 3 O 3 S 2
Brief description	yellowish odorless powder
External identifiers / databases
EC number	601-473-1
ECHA InfoCard	100.129.367
Wikidata	Q1434399
properties
Molar mass	403.88 g mol −1
Physical state	firmly
density	0.43 g cm −3
Melting point	105–106.5 ° C (decomposition)
solubility	practically insoluble in water; soluble in acetone , acetonitrile , dichloromethane , ethyl acetate and toluene ;
safety instructions
H and P phrases	H: 319-400
	P: 273-305 + 351 + 338
Toxicological data	> 5000 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 .

Fluthiacet-methyl is a cis - trans mixture from the group of thiadiazoles or imines and a derivative of fluthiacet .

Extraction and presentation

Fluthiacet-methyl can be produced by a multi-stage reaction beginning with the reaction of 4-chloro-2-fluoroacetanilide with disulphur dichloride in the presence of aluminum chloride , removal of the protective group and generation of the corresponding mercaptonanilline, reaction of the intermediate product with carbon disulphide in the presence of an amine and subsequent reaction with methyl chloroformate , Hexahydropyridazine and phosgene can be obtained.

properties

Fluthiacet-methyl is a yellowish solid that is practically insoluble in water.

use

Fluthiacet-methyl is used as a herbicide . It was discovered by Kumiai Chemical , investigated by Novartis for its potential uses and first approved in the USA in 1999. It is used against annual broadleaf weeds in soybean , corn and cotton plantations. The effect is based on the inhibition of protoporphyrinogen oxidase (PROTOX).

Admission

Fluthiacet-methyl is not on the list of active ingredients for pesticides permitted in the European Union . In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ EPA: Pesticide Factsheet Fluthiacet-methyl (PDF; 46 kB).
↑ ^a ^b ^c data sheet Fluthiacet-methyl from Sigma-Aldrich , accessed on May 22, 2017 ( PDF ).
↑ ^a ^b Peter Böger, Ko Wakabayashi: Peroxidizing Herbicides . Springer, 1999, ISBN 3-540-64550-0 , pp. 45, 84, 284 ( limited preview in Google Book search).
^ Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.

[EPA-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ EPA: Pesticide Factsheet Fluthiacet-methyl (PDF; 46 kB).

[Sigma-2] ta sheet Fluthiacet-methyl from Sigma-Aldrich , accessed on May 22, 2017 ( PDF ).

[Peter_Böger,_Ko_Wakabayashi-3] Peter Böger, Ko Wakabayashi: Peroxidizing Herbicides . Springer, 1999, ISBN 3-540-64550-0 , pp. 45, 84, 284 ( limited preview in Google Book search).

[PSM-4] Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.