Metamitron

Structural formula
General
Surname	Metamitron
other names	4-Amino-3-methyl-6-phenyl-1,2,4-triazin-5-one; Goltix;
Molecular formula	C 10 H 10 N 4 O
Brief description	yellowish solid
External identifiers / databases
EC number	255-349-3
ECHA InfoCard	100.050.301
PubChem	38854
Wikidata	Q2293747
properties
Molar mass	202.22 g mol −1
Physical state	firmly
density	1.350 g cm −3
Melting point	166.6 ° C
Vapor pressure	8.6 10 −9 hPa (20 ° C)
solubility	heavy in water (1700 mg l −1 at 20 ° C)
safety instructions
H and P phrases	H: 302-400
	P: 273
Toxicological data	1450 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 .

Metamitron is a chemical compound from the triazinone group .

Extraction and presentation

Metamitron can be obtained through a multi-stage reaction. Initially, benzoyl cyanide is reacted with sulfuric acid to form phenylglyoxylic acid and further with methanol . The intermediate product formed is reacted with acetylhydrazine , which in turn can be prepared from methyl acetate . In the further synthesis, the product is reacted with and hydrazine hydrate . Metamitron is finally formed through ring closure .

properties

Metamitron is a colorless solid that is very sparingly soluble in water. It rapidly decomposes through photolysis with deamination , is stable to acids and decomposes when exposed to bases with a pH value greater than 10.

use

Metamitron is used as a herbicide on beets against dicotyledon seed weeds in pre- and post-emergence. It was brought onto the market by Bayer AG in the mid-1970s under the name Goltix. Metamitron is also used to thin apples and pears. A short-term reduction in photosynthesis increases the fall of less developed fruits.

Admission

The active ingredient Metamitron was approved for use as a herbicide in the European Union with effect from September 1, 2009. In Germany, Austria and Switzerland, plant protection products with this active ingredient are approved.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on 4-Amino-3-methyl-6-phenyl-1,2,4-triazin-5-one in the GESTIS substance database of the IFA , accessed on February 9, 2017(JavaScript required) .
↑ Metamitron data sheet , PESTANAL at Sigma-Aldrich , accessed on March 9, 2013 ( PDF ).
^ Müfit Bahadir, Harun Parlar, Michael Spiteller: Springer Umweltlexikon . Springer DE, 2000, ISBN 3-642-56998-6 , pp. 758 ( limited preview in Google Book search).
↑ Entry on 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5-ones 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 0-08-095716-1 , pp. 671 ( limited preview in Google Book search).
^ Terence Robert Roberts, David Herd Hutson: Metabolic Pathways of Agrochemicals: Part 1: Herbicides and Plant Growth ... Royal Society of Chemistry, 1998, ISBN 0-85404-494-9 , pp. 660 ( limited preview in Google Book search).
↑ Rudolf Heitefuss: Plant protection . Georg Thieme Verlag, 2000, ISBN 3-13-513303-6 , p. 219 ( limited preview in Google Book search).
↑ Janis Mc Farland, Orvin Burnside: The Triazine Herbicides . Elsevier, 2011, ISBN 0-08-055963-8 , pp. 39 ( limited preview in Google Book search).
↑ Product description from ADAMA Austria , accessed on May 23, 2018.
↑ Directive 2008/125 / EC of the Commission of December 19, 2008 amending Directive 91/414 / EEC of the Council to include aluminum phosphide, calcium phosphide, magnesium phosphide, cymoxanil, dodemorph, 2,5-dichlorobenzoate, metamitron, sulcotrione, tebuconazole and Triadimenol as active ingredients (PDF)
↑ General Directorate Health and Food Safety of the European Commission: Entry on Metamitron in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on 4-Amino-3-methyl-6-phenyl-1,2,4-triazin-5-one in the GESTIS substance database of the IFA , accessed on February 9, 2017(JavaScript required) .

[Sigma-2] Metamitron data sheet , PESTANAL at Sigma-Aldrich , accessed on March 9, 2013 ( PDF ).

[Müfit_Bahadir,_Harun_Parlar,_Michael_Spiteller-3] Müfit Bahadir, Harun Parlar, Michael Spiteller: Springer Umweltlexikon . Springer DE, 2000, ISBN 3-642-56998-6 , pp. 758 ( limited preview in Google Book search).

[CLP_100.050.301-4] Entry on 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5-ones 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-5] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-08-095716-1 , pp. 671 ( limited preview in Google Book search).

[Terence_Robert_Roberts,_David_Herd_Hutson-6] Terence Robert Roberts, David Herd Hutson: Metabolic Pathways of Agrochemicals: Part 1: Herbicides and Plant Growth ... Royal Society of Chemistry, 1998, ISBN 0-85404-494-9 , pp. 660 ( limited preview in Google Book search).

[Rudolf_Heitefuss-7] Rudolf Heitefuss: Plant protection . Georg Thieme Verlag, 2000, ISBN 3-13-513303-6 , p. 219 ( limited preview in Google Book search).

[Janis_Mc_Farland,_Orvin_Burnside-8] Janis Mc Farland, Orvin Burnside: The Triazine Herbicides . Elsevier, 2011, ISBN 0-08-055963-8 , pp. 39 ( limited preview in Google Book search).

[9] Product description from ADAMA Austria , accessed on May 23, 2018.

[10] Directive 2008/125 / EC of the Commission of December 19, 2008 amending Directive 91/414 / EEC of the Council to include aluminum phosphide, calcium phosphide, magnesium phosphide, cymoxanil, dodemorph, 2,5-dichlorobenzoate, metamitron, sulcotrione, tebuconazole and Triadimenol as active ingredients (PDF)

[PSM-11] General Directorate Health and Food Safety of the European Commission: Entry on Metamitron in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.