Hexazinone

Structural formula
General
Surname	Hexazinone
other names	3-Cyclohexyl-6-dimethylamino-1-methyl-1,2,3,4-tetrahydro-1,3,5-triazine-2,4-dione
Molecular formula	C 12 H 20 N 4 O 2
Brief description	colorless and odorless solid
External identifiers / databases
EC number	257-074-4
ECHA InfoCard	100,051,869
PubChem	39965
Wikidata	Q408234
properties
Molar mass	252.32 g mol −1
Physical state	firmly
density	1.25 g cm −3
Melting point	115-117 ° C
boiling point	decomposes
Vapor pressure	0.03 mPa (25 ° C)
solubility	soluble in water, chloroform, methanol, benzene, dimethylformamide, acetone, toluene and hexane
safety instructions
H and P phrases	H: 302-319-410
	P: 273-305 + 351 + 338-501
Toxicological data	1690 mg kg −1 ( LD 50 , rat , oral ) ; 5280 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hexazinone is an active ingredient for crop protection and a chemical compound from the group of triazines and diketones ( triazinones ).

Extraction and presentation

Hexazinone can be obtained by reacting methyl chloroformate with cyanamide , followed by methylation and reaction with dimethylamine and cyclohexyl isocyanate .

An alternative representation is based on 2-methylthiopseudourea:

properties

Hexazinone is a colorless and odorless solid that is soluble in water.

use

Hexazinone is used as a herbicide . It has been sold by DuPont under the trade name Velpar since 1974 and is mainly used for alfalfa , sugar cane and pineapple . It is a non-selective leaf and soil herbicide effective against monocotyledonous and dicotyledonous plants.

Admission

In Germany it was contained in three approved plant protection products until 1991, the use of which was still permitted until the unrestricted indication requirement came into effect on July 1, 2001. Hexazinone has been in the list of active substances not included in Annex I of Directive 91/414 / EEC since 2002, so its use in plant protection products is not permitted in the EU.

In the EU states including Germany and Austria as well as in Switzerland no pesticides with this active substance are permitted.

Web links

US Department of agriculture forest service: Herbicide information profile of Hexazinone
FAO: Hexazinon-2012 (PDF; 158 kB)
CDPR: Hexazinon (PDF; 61 kB)
EPA: Reregistration Eligibility Decision (RED) Hexazinone (PDF; 1.1 MB)

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on hexazinone in the GESTIS substance database of the IFA , accessed on February 10, 2017(JavaScript required) .
↑ ^a ^b Entry on hexazinone in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 27, 2014.
↑ ^a ^b United States. Environmental Protection Agency: Pesticide Fact Handbook, Volume 2 . 1990, ISBN 978-0-8155-1239-4 ( page 337 in the google book search).
↑ Entry on 3-cyclohexyl-6-dimethylamino-1-methyl-1,2,3,4-tetrahydro-1,3,5-triazine-2,4-dione in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Ullmann's Agrochemicals, Volume 1 . Viley, 2007, ISBN 978-3-527-31604-5 ( page 819 in the Google book search).
↑ DuPont: Velpar
↑ Homer M. LeBaron, Janis E. McFarland, Orvin Burnside: The triazine herbicides: 50 years revolutionizing agriculture . 2002, ISBN 978-0-444-51167-6 ( page 39 in the Google book search).
↑ Drinking water glossary in the Pinneberg district
↑ Regulation (EC) No. 2076/2002 (PDF) of the Commission of November 20, 2002 to extend the deadline according to Article 8 (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 the approval of plant protection products with these active substances.
↑ General Directorate Health and Food Safety of the European Commission: Entry on Hexazinone in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on hexazinone in the GESTIS substance database of the IFA , accessed on February 10, 2017(JavaScript required) .

[ppdb-2] Entry on hexazinone in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 27, 2014.

[EPA-3] United States. Environmental Protection Agency: Pesticide Fact Handbook, Volume 2 . 1990, ISBN 978-0-8155-1239-4 ( page 337 in the google book search).

[CLP_100.051.869-4] Entry on 3-cyclohexyl-6-dimethylamino-1-methyl-1,2,3,4-tetrahydro-1,3,5-triazine-2,4-dione in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[ullmann-5] Ullmann's Agrochemicals, Volume 1 . Viley, 2007, ISBN 978-3-527-31604-5 ( page 819 in the Google book search).

[6] DuPont: Velpar

[buch-7] Homer M. LeBaron, Janis E. McFarland, Orvin Burnside: The triazine herbicides: 50 years revolutionizing agriculture . 2002, ISBN 978-0-444-51167-6 ( page 39 in the Google book search).

[8] Drinking water glossary in the Pinneberg district

[9] Regulation (EC) No. 2076/2002 (PDF) of the Commission of November 20, 2002 to extend the deadline according to Article 8 (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 the approval of plant protection products with these active substances.

[PSM-10] General Directorate Health and Food Safety of the European Commission: Entry on Hexazinone in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.