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Merck
CN

36154

Metamitron

PESTANAL®, analytical standard

Synonym(s):

4-Amino-4,5-dihydro-3-methyl-6-phenyl-1,2,4-triazin-5-one

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About This Item

Empirical Formula (Hill Notation):
C10H10N4O
CAS Number:
41394-05-2
Molecular Weight:
202.21
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329755299
EC Number:
255-349-3
Beilstein/REAXYS Number:
613129
MDL number:
MFCD00055524

Key Documents

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Product Name

Metamitron, PESTANAL®, analytical standard

InChI key

VHCNQEUWZYOAEV-UHFFFAOYSA-N

InChI

1S/C10H10N4O/c1-7-12-13-9(10(15)14(7)11)8-5-3-2-4-6-8/h2-6H,11H2,1H3

SMILES string

CC1=NN=C(c2ccccc2)C(=O)N1N

grade

analytical standard

product line

PESTANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
NMR: suitable
gas chromatography (GC): suitable

impurities

≤0.5% water (Karl Fischer)

mp

165-170 °C

suitability

passes test for identity (NMR)

application(s)

agriculture
environmental

format

neat

Quality Level

100

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

General description

Metamitron is a 1,2,4-triazine herbicide, which is yellow crystalline in nature and can easily degrade in soil to form stable metabolites. It can be prepared via reaction of N-acetyl-benzylhydrazone with hydroxylamine in the presence of potassium hydroxide in pyridine.

Legal Information

PESTANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

农药列管产品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCN4881
BCCN3313
BCCG3136
BCCF4712
BCBS8319V

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The Pesticide Encyclopedia (2014)
Adsorption of 1, 2, 4-triazine pesticides metamitron and metribuzin on lignin
Ludvik J and Zuman P
Microchemical Journal, Devoted to the Application of Microtechniques in All Branches of Science, 64, 15-20 (2000)
E Mechant et al.
Communications in agricultural and applied biological sciences, 75(2), 53-59 (2010-01-01)
Chenopodium album L. (fat-hen) with a Ser264-Gly mutation is resistant to photosystem II-inhibiting herbicides like the triazinone metamitron, a key herbicide in sugar beet. In recent years, this resistant biotype may cause unsatisfactory weed control in Belgian sugar beet. However
Jirí Ludvík et al.
Acta crystallographica. Section C, Crystal structure communications, 63(Pt 4), o259-o262 (2007-04-07)
The title structures, both C(10)H(10)N(4)O, are substitutional isomers. The N-N bond lengths are longer and the C=N bond lengths are shorter by ca 0.025 A than the respective average values in the C=N-N=C group of asymmetric triazines; the assessed respective
T De Marez et al.
Communications in agricultural and applied biological sciences, 72(2), 265-269 (2008-04-11)
Seeds of various fat-hen populations (Chenopodium album L.), mostly originating from sugar beet fields, were subjected to treatments with the following herbicides: metamitron, acetochlor, dimethenamid-P and S-metolachlor. Herbicides were applied either incorporated into a sandy Loam soil (2005-2007) and/or on
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