Metribuzin

Structural formula
General
Surname	Metribuzin
other names	4-Amino-6- tert- butyl-3-methylthio-1,2,4-triazin-5-one; Sencor;
Molecular formula	C 8 H 14 N 4 OS
Brief description	colorless solid with a characteristic odor
External identifiers / databases
EC number	244-209-7
ECHA InfoCard	100.040.175
PubChem	30479
Wikidata	Q421450
properties
Molar mass	214.28 g mol −1
Physical state	firmly
density	1.28 g cm −3
Melting point	126.2 ° C
boiling point	132 ° C (0.02 mbar)
solubility	heavy in water (1.05 g l −1 at 20 ° C)
safety instructions
H and P phrases	H: 302-331-410
	P: 261-273-311-501
Toxicological data	1100 mg kg −1 ( LD 50 , rat , oral ) ; 20,000 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 .

Metribuzin is an active ingredient for crop protection and a chemical compound from the group of triazinones .

Extraction and presentation

Metribuzin can be obtained by a multi-stage reaction of pinacolone with sulfuryl chloride and dimethylamine and subsequent reaction of the intermediate products with sodium hydroxide , thiocarbonohydrazide and methyl iodide or methyl bromide .

properties

Metribuzin is a flammable, colorless solid with a characteristic odor that is sparingly soluble in water.

use

Metribuzin is used as an active ingredient in crop protection products. It is used as a herbicide when applied to potatoes, wheat, tomatoes, carrots and others and works by inhibiting the transport of electrons during photosynthesis. It is often used in combination with other pesticides, for example under the trade names Saline (with Trifluralin ) and Turbo (with Metolachlor ); on its own, for example, it bears the trade names Mistral or Sencor. Metribuzin was registered for use as a herbicide in the United States in 1973. A standard registration (PB86-NTIS # 174216) was issued in July 1985. In 2011 just under 1000 t of metribuzin were used there.

Admission

In the European Union, Metribuzin was added to the list of permitted active ingredients in pesticides with effect from October 1, 2007. In Germany, Austria and Switzerland, plant protection products with this active ingredient are approved.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on Metribuzin in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ Entry on Metribuzin 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 .
↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 672 ( limited preview in Google Book search).
↑ ^a ^b EPA: Metribuzine (PDF; 757 kB).
↑ Directive 2007/25 / EC (PDF) of the Commission of April 23, 2007 amending Council Directive 91/414 / EEC to include the active substances dimethoate, dimethomorph, glufosinate, metribuzin, phosmet and propamocarb.
↑ General Directorate Health and Food Safety of the European Commission: Entry on Metribuzin 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 ⁱ ^j ^k ^l Entry on Metribuzin in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[CLP_100.040.175-2] Entry on Metribuzin 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 .

[Unger-3] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 672 ( limited preview in Google Book search).

[EPA-4] EPA: Metribuzine (PDF; 757 kB).

[5] Directive 2007/25 / EC (PDF) of the Commission of April 23, 2007 amending Council Directive 91/414 / EEC to include the active substances dimethoate, dimethomorph, glufosinate, metribuzin, phosmet and propamocarb.

[PSM-6] General Directorate Health and Food Safety of the European Commission: Entry on Metribuzin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.