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
CAS Number	21087-64-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34846 ;
ChemSpider	28287;
ECHA InfoCard	100.040.175
PubChem CID	30479;
UNII	QO836138OV ;
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
Density	1.31 g/cm3
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/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

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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

^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0430". National Institute for Occupational Safety and Health (NIOSH).
^ 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.
^ 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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[PGCH-1] ^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0430". National Institute for Occupational Safety and Health (NIOSH).

[RobertsHutson1998-2] 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.

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