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[1]
Density	1.31 g/cm3
Melting point	125 °C (257 °F; 398 K)
Solubility in water	0.1% (20 °C)[1]
Vapor pressure	0.0000004 mmHg (20 °C)[1]
Hazards
NIOSH (US health exposure limits):
PEL (Permissible)	none[1]
REL (Recommended)	5 mg/m3[1]
IDLH (Immediate danger)	N.D.[1]
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.^[2] It is widely used in agriculture and has been found to contaminate groundwater.^[3]

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]}