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Metribuzin

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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
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.040.175 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H14N4OS/c1-8(2,3)5-6(13)12(9)7(14-4)11-10-5/h9H2,1-4H3Key: FOXFZRUHNHCZPX-UHFFFAOYSA-N
  • InChI=1/C8H14N4OS/c1-8(2,3)5-6(13)12(9)7(14-4)11-10-5/h9H2,1-4H3Key: FOXFZRUHNHCZPX-UHFFFAOYAI
SMILES
  • CC(C)(C)C1=NN=C(N(C1=O)N)SC
Properties
Chemical formula C8H14N4OS
Molar mass 214.29 g·mol
Appearance Colorless, crystalline solid
Density 1.31 g/cm
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/m
IDLH (Immediate danger) N.D.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

References

  1. ^ 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.

External links

  • Metribuzin in the Pesticide Properties DataBase (PPDB)
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