Metribuzin | CAS#21087-64-9 | triazine herbicide

MedKoo Cat#: 598753 | Name: Metribuzin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Metribuzin is a triazine herbicide.

Chemical Structure

Metribuzin

CAS#21087-64-9

Theoretical Analysis

MedKoo Cat#: 598753

Name: Metribuzin

CAS#: 21087-64-9

Chemical Formula: C8H14N4OS

Exact Mass: 214.0888

Molecular Weight: 214.29

Elemental Analysis: C, 44.84; H, 6.59; N, 26.15; O, 7.47; S, 14.96

Price and Availability

Size	Price	Availability	Quantity
1g	USD 450.00	2 Weeks

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Synonym

Metribuzin; Sencor; DIC 1468; BAY 61597; BAY-61597; BAY61597;

IUPAC/Chemical Name

4-amino-6-(tert-butyl)-3-(methylthio)-1,2,4-triazin-5(4H)-one

InChi Key

FOXFZRUHNHCZPX-UHFFFAOYSA-N

InChi Code

InChI=1S/C8H14N4OS/c1-8(2,3)5-6(13)12(9)7(14-4)11-10-5/h9H2,1-4H3

SMILES Code

O=C1N(N)C(SC)=NN=C1C(C)(C)C

Appearance

Solid powder

Purity

>97% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Metribuzin hinders DNA synthesis in treated plants and acts on photosystem II, ultimately inhibiting photosynthesis.

In vitro activity:

In this study, it was hypothesized that growth-inhibiting concentrations of the herbicide metribuzin impair the ability of Scenedesmus obliquus to form colonies in response to the surfactant morphogen FFD-6. The results confirmed that the formation of colonies in S. obliquus was hampered by metribuzin. EC50 values of metribuzin for colony inhibition (approximately 11 μg L(-1)) were similar to those for growth and photosynthesis inhibition (12-25 μg metribuzinL(-1)). Reference: Chemosphere. 2011 Jan;82(3):411-7. https://pubmed.ncbi.nlm.nih.gov/20971494/

In vivo activity:

Crayfish were exposed to metribuzin concentrations of 0.52 μg x l(-1) (realistic environmental concentration) and 3.06 mg x l(-1) (10% 96hLC50) for 10 and 30 days followed by a 30-day depuration period without exposure to metribuzin. Chronic exposure of metribuzin resulted in oxidative damage to cell lipids, in changes of antioxidant activity in crayfish tissue, and pathological changes in hepatopancreas. The results suggest that selected oxidative stress biomarkers, antioxidant enzymes, and pathologies of hepatopancreas may have potential as biomarkers for monitoring residual triazine herbicides in the aquatic environment. Reference: Neuro Endocrinol Lett. 2014;35 Suppl 2:51-6. https://pubmed.ncbi.nlm.nih.gov/25638366/

Preparing Stock Solutions

The following data is based on the product molecular weight 214.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Pilcher W, Zandkarimi H, Arceneaux K, Harrison S, Baisakh N. Genome-wide microarray analysis leads to identification of genes in response to herbicide, metribuzin in wheat leaves. PLoS One. 2017 Dec 11;12(12):e0189639. doi: 10.1371/journal.pone.0189639. Erratum in: PLoS One. 2018 Jun 19;13(6):e0199564. PMID: 29228046; PMCID: PMC5724888. 2. Lürling M. Metribuzin impairs the unicell-colony transformation in the green alga Scenedesmus obliquus. Chemosphere. 2011 Jan;82(3):411-7. doi: 10.1016/j.chemosphere.2010.09.070. Epub 2010 Oct 23. PMID: 20971494. 3. Koutnik D, Stara A, Zuskova E, Kouba A, Velisek J. The effect of subchronic metribuzin exposure to signal crayfish (Pacifastacus leniusculus Dana 1852). Neuro Endocrinol Lett. 2014;35 Suppl 2:51-6. PMID: 25638366.

In vitro protocol:

In vivo protocol:

1. Koutnik D, Stara A, Zuskova E, Kouba A, Velisek J. The effect of subchronic metribuzin exposure to signal crayfish (Pacifastacus leniusculus Dana 1852). Neuro Endocrinol Lett. 2014;35 Suppl 2:51-6. PMID: 25638366.

1: Zhang H, Zhang Y, Hou Z, Wu X, Gao H, Sun F, Pan H. Biodegradation of triazine herbicide metribuzin by the strain Bacillus sp. N1. J Environ Sci Health B. 2014;49(2):79-86. doi: 10.1080/03601234.2014.844610. PubMed PMID: 24328539. 2: Sahoo S, Manjaiah KM, Datta SC, Ahmed Shabeer TP, Kumar J. Kinetics of metribuzin release from bentonite-polymer composites in water. J Environ Sci Health B. 2014;49(8):591-600. doi: 10.1080/03601234.2014.911578. PubMed PMID: 24901962. 3: Koutnik D, Stara A, Zuskova E, Kouba A, Velisek J. The effect of subchronic metribuzin exposure to signal crayfish (Pacifastacus leniusculus Dana 1852). Neuro Endocrinol Lett. 2014;35 Suppl 2:51-6. PubMed PMID: 25638366. 4: Singh N, Raunaq, Singh SB. Effect of fly ash amendment on persistence of metribuzin in soils. J Environ Sci Health B. 2013;48(2):108-13. doi: 10.1080/03601234.2013.726893. PubMed PMID: 23305278. 5: Flores Céspedes F, Pérez García S, Villafranca Sánchez M, Fernández Pérez M. Bentonite and anthracite in alginate-based controlled release formulations to reduce leaching of chloridazon and metribuzin in a calcareous soil. Chemosphere. 2013 Aug;92(8):918-24. doi: 10.1016/j.chemosphere.2013.03.001. Epub 2013 Apr 4. PubMed PMID: 23562547. 6: Oukali-Haouchine O, Barriuso E, Mayata Y, Moussaoui KM. Factors affecting metribuzin retention in Algerian soils and assessment of the risks of contamination. Environ Monit Assess. 2013 May;185(5):4107-15. doi: 10.1007/s10661-012-2853-0. Epub 2012 Aug 29. PubMed PMID: 22930189. 7: Singh N, Raunaq, Singh SB. Reduced downward mobility of metribuzin in fly ash-amended soils. J Environ Sci Health B. 2013;48(7):587-92. doi: 10.1080/03601234.2013.774934. PubMed PMID: 23581692. 8: López-Piñeiro A, Peña D, Albarrán A, Becerra D, Sánchez-Llerena J. Sorption, leaching and persistence of metribuzin in Mediterranean soils amended with olive mill waste of different degrees of organic matter maturity. J Environ Manage. 2013 Jun 15;122:76-84. doi: 10.1016/j.jenvman.2013.03.006. Epub 2013 Apr 3. PubMed PMID: 23562950. 9: Boyandin AN, Zhila NO, Kiselev EG, Volova TG. Constructing Slow-Release Formulations of Metribuzin Based on Degradable Poly(3-hydroxybutyrate). J Agric Food Chem. 2016 Jul 20;64(28):5625-32. doi: 10.1021/acs.jafc.5b05896. Epub 2016 Jul 11. PubMed PMID: 27356030. 10: Peña D, López-Piñeiro A, Albarrán Á, Rato-Nunes JM, Sánchez-Llerena J, Becerra D, Ramírez M. De-oiled two-phase olive mill waste may reduce water contamination by metribuzin. Sci Total Environ. 2016 Jan 15;541:638-645. doi: 10.1016/j.scitotenv.2015.09.019. Epub 2015 Oct 2. PubMed PMID: 26437341. 11: Volova TG, Zhila NO, Vinogradova ON, Nikolaeva ED, Kiselev EG, Shumilova AA, Shershneva AM, Shishatskaya EI. Constructing herbicide metribuzin sustained-release formulations based on the natural polymer poly-3-hydroxybutyrate as a degradable matrix. J Environ Sci Health B. 2016 Feb;51(2):113-125. Epub 2015 Nov 30. PubMed PMID: 26621217. 12: Plhalova L, Stepanova S, Praskova E, Chromcova L, Zelnickova L, Divisova L, Skoric M, Pistekova V, Bedanova I, Svobodova Z. The effects of subchronic exposure to metribuzin on Danio rerio. ScientificWorldJournal. 2012;2012:728189. doi: 10.1100/2012/728189. Epub 2012 Jun 18. PubMed PMID: 22792050; PubMed Central PMCID: PMC3385604. 13: Singh N, Bala Singh S, Raunaq, Das TK. Effect of fly ash on persistence, mobility and bio-efficacy of metribuzin and metsulfuron-methyl in crop fields. Ecotoxicol Environ Saf. 2013 Nov;97:236-41. doi: 10.1016/j.ecoenv.2013.07.031. Epub 2013 Aug 20. PubMed PMID: 23972318. 14: Volova T, Zhila N, Kiselev E, Prudnikova S, Vinogradova O, Nikolaeva E, Shumilova A, Shershneva A, Shishatskaya E. Poly(3-hydroxybutyrate)/metribuzin formulations: characterization, controlled release properties, herbicidal activity, and effect on soil microorganisms. Environ Sci Pollut Res Int. 2016 Dec;23(23):23936-23950. Epub 2016 Sep 15. PubMed PMID: 27628924. 15: Husak VV, Mosiichuk NM, Maksymiv IV, Storey JM, Storey KB, Lushchak VI. Oxidative stress responses in gills of goldfish, Carassius auratus, exposed to the metribuzin-containing herbicide Sencor. Environ Toxicol Pharmacol. 2016 Jul;45:163-9. doi: 10.1016/j.etap.2016.05.028. Epub 2016 May 31. PubMed PMID: 27310208. 16: Singh N, Raunaq, Singh SB. Effect of fly ash on sorption behavior of metribuzin in agricultural soils. J Environ Sci Health B. 2012;47(2):89-98. doi: 10.1080/03601234.2012.616767. PubMed PMID: 22251208. 17: Lürling M. Metribuzin impairs the unicell-colony transformation in the green alga Scenedesmus obliquus. Chemosphere. 2011 Jan;82(3):411-7. doi: 10.1016/j.chemosphere.2010.09.070. Epub 2010 Oct 23. PubMed PMID: 20971494. 18: Undabeytia T, Recio E, Maqueda C, Morillo E, Gómez-Pantoja E, Sánchez-Verdejo T. Reduced metribuzin pollution with phosphatidylcholine-clay formulations. Pest Manag Sci. 2011 Mar;67(3):271-8. doi: 10.1002/ps.2060. Epub 2010 Nov 19. PubMed PMID: 21308953. 19: Hostovsky M, Blahova J, Plhalova L, Stepanova S, Praskova E, Marsalek P, Svobodova Z. Oxidative stress parameters in early developmental stages of common carp (Cyprinus carpio L.) after subchronic exposure to terbuthylazine and metribuzin. Neuro Endocrinol Lett. 2012;33 Suppl 3:124-9. PubMed PMID: 23353855. 20: Delancey JO, Alavanja MC, Coble J, Blair A, Hoppin JA, Austin HD, Beane Freeman LE. Occupational exposure to metribuzin and the incidence of cancer in the Agricultural Health Study. Ann Epidemiol. 2009 Jun;19(6):388-95. doi: 10.1016/j.annepidem.2008.12.018. Epub 2009 Apr 15. PubMed PMID: 19369095; PubMed Central PMCID: PMC2693328.