Methabenzthiazuron

Structural formula
General
Surname	Methabenzthiazuron
other names	1- (1,3-Benzothiazol-2-yl) -1,3-dimethylurea
Molecular formula	C 10 H 11 N 3 OS
Brief description	colorless solid
External identifiers / databases
EC number	242-505-0
ECHA InfoCard	100.038.625
PubChem	29216
Wikidata	Q15632903
properties
Molar mass	221.28 g mol −1
Physical state	firmly
density	1.33 g cm −3 (bulk density)
Melting point	119-121 ° C
Vapor pressure	5.9 10 −6 Pa (20 ° C)
solubility	practically insoluble in water (59 mg l −1 at 20 ° C); soluble in acetone and toluene;
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 410
	P: 273-501
Toxicological data	2500 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 .

Methabenzthiazuron is a chemical compound from the group of benzothiazoles .

Extraction and presentation

Methabenzthiazuron can be obtained by reacting benzothiazole with methylhydroxylamine to form 2-methylaminobenzothiazole and its reaction with methyl isocyanate . Alternatively, the synthesis is possible by reacting mercaptobenzothiazole with thionyl chloride , methylamine and methyl isocyanate.

properties

Methabenzthiazuron is a colorless solid that is practically insoluble in water. It is unstable in strong acids and alkalis, but has a DT ₅₀ value of more than a year at a pH value of 4 to 9 at 22 ° C. It is also stable to direct photolysis .

use

Methabenzthiazuron is used as an algicide and herbicide . It is used to control a range of weeds and grasses in cereals, legumes, corn, garlic and onions. In combination with other herbicides, it is also used in the vineyards and orchards. The effect is based on the inhibition of photosynthetic electron transport ( PS II ).

Admission

Methabenzthiazuron was approved in the GDR between 1972 and 1994 and in the FRG between 1971 and 1996.

In 2006, the EU Commission decided not to grant approval of active substances for methabenzthiazuron. For existing approvals, transition periods were planned until the end of 2009. In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

Individual evidence

↑ ^a ^b ^c Entry on methabenzthiazuron in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.
↑ ^a ^b ^c ^d ^e ^f ^g Entry on methabenzthiazuron in the GESTIS substance database of the IFA , accessed on February 14, 2017(JavaScript required) .
^ ^A ^b ^c Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals, Volume 2 . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 , pp. 749 ff . ( limited preview in Google Book search).
↑ Entry on methabenzthiazuron in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 424 ( limited preview in Google Book search).
↑ Peter Brandt (Ed.): Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer, 2010, ISBN 978-3-0348-0028-0 , pp. 26 ( limited preview in Google Book search).
↑ Decision of the Commission of April 25, 2006 on the non-inclusion of methabenzthiazuron in Annex I of Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products with this active substance (PDF)
↑ General Directorate Health and Food Safety of the European Commission: Entry on methabenzthiazuron in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 24, 2016.

[PPDB-1] Entry on methabenzthiazuron in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on methabenzthiazuron in the GESTIS substance database of the IFA , accessed on February 14, 2017(JavaScript required) .

[Roberts2-3] A ^b ^c Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals, Volume 2 . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 , pp. 749 ff . ( limited preview in Google Book search).

[CLP_100.038.625-4] Entry on methabenzthiazuron in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[Unger-5] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 424 ( limited preview in Google Book search).

[herausgegeben_von_Peter_Brandt-6] Peter Brandt (Ed.): Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer, 2010, ISBN 978-3-0348-0028-0 , pp. 26 ( limited preview in Google Book search).

[7] Decision of the Commission of April 25, 2006 on the non-inclusion of methabenzthiazuron in Annex I of Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products with this active substance (PDF)

[PSM-8] General Directorate Health and Food Safety of the European Commission: Entry on methabenzthiazuron in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 24, 2016.