Metamiton

Names

[ Name ]:
Metamiton

[Synonym ]:
4-Amino-4,5-dihydro-3-methyl-6-phenyl-1,2,4-triazin-5-one
Herbrak
1,2,4-Triazin-5(4H)-one, 4-amino-3-methyl-6-phenyl-
Metamiton
Metron Stefes
Metamitron [BSI:ISO]
Goltix
MFCD00055524
T6NN DNVJ C1 DZ FR
4-amino-3-methyl-6-phenyl-4,5-dihydro-1,2,4-triazin-5-one
Methiamitron [Belgium]
METAMITRON
4-amino-6-phenyl-3-methyl-4,5-dihydro-1,2,4-triazin-5-one
BAY DRW 1139
Goltix WG 70
UNII-H69RGO1QO6
4-amino-3-methyl-6-phenyl-1,2,4-triazin-5-(4H)-one
Metamitron [German]
Methiamitron [French]
4-Amino-3-methyl-6-phenyl-1,2,4-triazin-5-one
EINECS 255-349-3
4-Amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one

Biological Activity

[Description]:

Metamitron is a pre- and post-emergence herbicide used for the control of broad-leaved weeds and grasses in sugar beet[1].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[References]

[1]. Shizong Wang, et al. Identification of Degradation Routes of Metamitron in Soil Microcosms Using 13 C-isotope Labeling. Environ Pollut. 2017 Jan;220(Pt B):927-935.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
335.8±25.0 °C at 760 mmHg

[ Melting Point ]:
167-170 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₀N₄O

[ Molecular Weight ]:
202.213

[ Flash Point ]:
156.9±23.2 °C

[ Exact Mass ]:
202.085464

[ PSA ]:
73.80000

[ LogP ]:
0.83

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.672

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XZ3015000

CHEMICAL NAME :: as-Triazin-5(4H)-one, 4-amino-3-methyl-6-phenyl-

CAS REGISTRY NUMBER :: 41394-05-2

BEILSTEIN REFERENCE NO. :: 0613129

LAST UPDATED :: 199710

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C10-H10-N4-O

MOLECULAR WEIGHT :: 202.24

WISWESSER LINE NOTATION :: T6NN DNVJ C1 DZ FR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1447 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >331 mg/m3/4H

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1450 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Bird - quail

DOSE/DURATION :: 1930 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Mold - Neurospora crassa

DOSE/DURATION :: 1 mg/L

REFERENCE :: ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 7(Suppl 3),11,1985

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H400

[ Precautionary Statements ]:
P273

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;N:Dangerousfortheenvironment;

[ Risk Phrases ]:
R22;R50

[ Safety Phrases ]:
S61-S45-S36/37

[ RIDADR ]:
UN 3077 9/PG 3

[ WGK Germany ]:
2

[ RTECS ]:
XZ3015000

[ Hazard Class ]:
9.0

[ HS Code ]:
2933699014

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933699014

[ Summary ]:
2933699014 4-amino-6-(tert-butyl)-3-(methylthio)-1,2,4-triazin-5(4h)-one。supervision conditions:s(import or export registration certificate for pesticides)。VAT:17.0%。tax rebate rate:9.0%。MFN tarrif:6.5%。general tariff:20.0%

Articles

Absorption, translocation and metabolism of metamitron in Chenopodium album.

Pest Manag. Sci. 68(2) , 209-16, (2012)

In recent years, common lambsquarters (Chenopodium album L.) populations from sugar beet fields in different European countries have responded as resistant to the as-triazinone metamitron. The populat...

Spectroscopic investigation and hydrogen-bonding analysis of triazinones.

J. Mol. Model. 18(8) , 3587-608, (2012)

NIR FT-Raman, FTIR and UV-vis spectra of the herbicide metamitron were recorded and analyzed. The aromaticities, equilibrium geometries, bonding features, electrostatic potentials, and harmonic vibrat...

Chlorophyll fluorescence protocol for quick detection of triazinone resistant Chenopodium album L.

Commun. Agric. Appl. Biol. Sci. 75(2) , 83-90, (2010)

Sugar beet growers in Europe are more often confronted with an unsatisfactory control of Chenopodium album L. (fat-hen), possibly due to the presence of a triazinone resistant biotype. So far, two mut...