Tebuthiuron

Structural formula
General
Surname	Tebuthiuron
other names	1- (5- tert -butyl-1,3,4-thiadiazol-2-yl) -1,3-dimethylurea
Molecular formula	C 9 H 16 N 4 OS
Brief description	colorless solid
External identifiers / databases
EC number	251-793-7
ECHA InfoCard	100.047.070
PubChem	5383
Wikidata	Q125986
properties
Molar mass	228.32 g mol −1
Physical state	firmly
density	1.1 g cm −3 (bulk density)
Melting point	161.5–164 ° C (decomposition)
Vapor pressure	3.6 hPa (20 ° C)
solubility	sparingly soluble in water (2.3 g l −1 at 25 ° C); soluble in acetone and methanol;
safety instructions
H and P phrases	H: 302-410
	P: 273-501
Toxicological data	644 mg kg −1 ( LD 50 , rat , oral ) ; 5000 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 .

Tebuthiuron is a chemical compound from the group of urea derivatives .

Extraction and presentation

Tebuthiuron can be obtained through a multi-stage reaction of methyl 2,2-dimethylpropionate with hydrazine , methylthiourea , sulfuric acid and methyl isocyanate .

properties

Tebuthiuron is a colorless solid that decomposes when heated before it reaches its melting point and is sparingly soluble in water.

use

Tebuthiuron is a relatively nonselective herbicide that is activated in the soil and works by inhibiting photosynthesis . It is used to control weeds, grasses and bushes on pasture land and a wide variety of industrial sites such as airports, industrial areas, non-agricultural areas such as roads and sidewalks. Primary areas of application are pasture land, railway systems and other industrial plants. It was approved in the United States in 1974.

Admission

Tebuthiuron was approved in the FRG between 1982 and 1986.

In the European Community it is not a permitted crop protection agent . In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

Individual evidence

^ ^A ^b Stanley A. Greene: Sittig's Handbook of Pesticides and Agricultural Chemicals . William Andrew, 2007, ISBN 0-8155-1903-6 , pp. 828 ( limited preview in Google Book search).
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on tebuthiuron in the GESTIS substance database of the IFA , accessed on February 7, 2017(JavaScript required) .
↑ ^a ^b Entry on Tebuthiuron in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 31, 2013.
↑ Tebuthiuron data sheet , PESTANAL at Sigma-Aldrich , accessed on August 11, 2012 ( PDF ).
↑ Entry on tebuthiuron 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 . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 618 ( limited preview in Google Book search).
↑ EPA: RED FACTS Tebuthiuron (PDF; 67 kB).
↑ Peter Brandt: Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer DE, 2010, ISBN 3-0348-0028-2 , pp. 26 ( limited preview in Google Book search).
↑ Regulation (EC) No. 2076/2002 of the Commission of November 20, 2002 extending the deadline in accordance with Article 8 paragraph 2 of Council Directive 91/414 / EEC and on the non-inclusion of certain active substances in Annex I of this directive and the revocation of Approvals of plant protection products with these active ingredients (PDF) .
↑ General Directorate Health and Food Safety of the European Commission: Entry on Tebuthiuron in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 25, 2016.

[Stanley_A._Greene-1] A ^b Stanley A. Greene: Sittig's Handbook of Pesticides and Agricultural Chemicals . William Andrew, 2007, ISBN 0-8155-1903-6 , pp. 828 ( limited preview in Google Book search).

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on tebuthiuron in the GESTIS substance database of the IFA , accessed on February 7, 2017(JavaScript required) .

[PPDB-3] Entry on Tebuthiuron in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 31, 2013.

[Sigma-4] Tebuthiuron data sheet , PESTANAL at Sigma-Aldrich , accessed on August 11, 2012 ( PDF ).

[CLP_100.047.070-5] Entry on tebuthiuron 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-6] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 618 ( limited preview in Google Book search).

[EPA-7] EPA: RED FACTS Tebuthiuron (PDF; 67 kB).

[Peter_Brandt-8] Peter Brandt: Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer DE, 2010, ISBN 3-0348-0028-2 , pp. 26 ( limited preview in Google Book search).

[9] Regulation (EC) No. 2076/2002 of the Commission of November 20, 2002 extending the deadline in accordance with Article 8 paragraph 2 of Council Directive 91/414 / EEC and on the non-inclusion of certain active substances in Annex I of this directive and the revocation of Approvals of plant protection products with these active ingredients (PDF) .

[PSM-10] General Directorate Health and Food Safety of the European Commission: Entry on Tebuthiuron in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 25, 2016.