Metribuzin

Metribuzin (4-amino-6-tert-butyl-3-(methylthio)-1,2,4-triazin-5(4H)-one) is a herbicide used both pre- and post-emergence in crops including soy bean, potatoes, tomatoes and sugar cane.

Metribuzin

Names
Preferred IUPAC name 3-Amino-5-tert-butyl-2-(methylsulfanyl)-1,2,4-triazin-5(4H)-one
Other names 4-Amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5(4H)-one
Identifiers
CAS Number	21087-64-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:34846 Y
ChemSpider	28287
ECHA InfoCard	100.040.175
PubChem CID	30479
UNII	QO836138OV Y
CompTox Dashboard (EPA)	DTXSID6024204
InChI InChI=1S/C8H14N4OS/c1-8(2,3)5-6(13)12(9)7(14-4)11-10-5/h9H2,1-4H3 Key: FOXFZRUHNHCZPX-UHFFFAOYSA-N InChI=1/C8H14N4OS/c1-8(2,3)5-6(13)12(9)7(14-4)11-10-5/h9H2,1-4H3 Key: FOXFZRUHNHCZPX-UHFFFAOYAI
SMILES CC(C)(C)C1=NN=C(N(C1=O)N)SC
Properties
Chemical formula	C8H14N4OS
Molar mass	214.29 g·mol−1
Appearance	Colorless, crystalline solid
Density	1.31 g/cm3
Melting point	125 °C (257 °F; 398 K)
Solubility in water	0.1% (20 °C)
Vapor pressure	0.0000004 mmHg (20 °C)
Hazards
NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	5 mg/m3
IDLH (Immediate danger)	N.D.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

It acts by inhibiting photosynthesis by disrupting photosystem II. It is widely used in agriculture and has been found to contaminate groundwater.

Metribuzin is produced by reacting one mole of 4-amino-6-tert-butyl-3-mercapto-(1,2,4)triazin-5(4H)one and half a mole of dimethyl sulfonate which react at 57°C in presence of sulfuric acid media about 7 hours and transfer methyl (CH₃) from triazine to metribuzin and product formed 1 mole of metribuzin and half mole of sulfuric acid and later neutralized with soda ash and then purified.^{[citation needed]}

MP=125°C, BP=132°C, and cause dust explosion if enough amount of energy absorbed by it.^{[citation needed]}