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Metribuzin

Metribuzin
Skeletal formula of metribuzin
Space-filling model of the metribuzin molecule
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 Edit this at Wikidata
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[1]
Density 1.31 g/cm3
Melting point 125 °C (257 °F; 398 K)
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).

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.[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]

References

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0430". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ Terence Robert Roberts; David Herd Hutson (17 July 1998). Metabolic Pathways of Agrochemicals: Herbicides and plant growth regulators. Royal Society of Chemistry. pp. 662–. ISBN 978-0-85404-494-8. Retrieved 25 May 2012.
  3. ^ Undabeytia, T. S.; Recio, E.; Maqueda, C.; Morillo, E.; Gómez-Pantoja, E.; Sánchez-Verdejo, T. (2011). "Reduced metribuzin pollution with phosphatidylcholine-clay formulations". Pest Management Science. 67 (3): 271–278. doi:10.1002/ps.2060. PMID 21308953.
  • Metribuzin in the Pesticide Properties DataBase (PPDB)
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