Metribuzin

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Metribuzin
Metribuzin.svg
Metribuzin-3D-spacefill.png
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
AppearanceColorless, 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 ]

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5
H
5−n
R
n
where R is a branched alkyl and n = 3 or 4. Representative examples are the tetraisopropyl derivative C
5
HiPr
4
and the tris(tert-butyl) derivative 1,2,4-C
5
H
2
tBu
3
. These ligands are so large that their complexes behave differently from the pentamethylcyclopentadienyl analogues. Because they cannot closely approach the metal, these bulky ligands stabilize high spin complexes, such as (C5H2tBu3)2Fe2I2. These large ligands stabilize highly unsaturated derivatives such as (C5H2tBu3)2Fe2N2.

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References

  1. 1 2 3 4 5 6 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.