Metribuzin

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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.040.175
UNII
  • 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
  • CC(C)(C)C1=NN=C(N(C1=O)N)SC
Properties
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)
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

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.

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.

MP=125 °C, BP=132 °C, and cause dust explosion if enough amount of energy absorbed by it.

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