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Metamitron

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Name

Metamitron

EINECS 255-349-3
CAS No. 41394-05-2 Density 1.34 g/cm3
PSA 73.80000 LogP 0.90870
Solubility 1.8g/L(20 oC) Melting Point 167-170 °C(lit.)
Formula C10H10N4O Boiling Point 335.8 °C at 760 mmHg
Molecular Weight 202.216 Flash Point 156.9 °C
Transport Information UN 3077 9/PG 3 Appearance ligh yellow crystall
Safety 61 Risk Codes 22-50
Molecular Structure Molecular Structure of 41394-05-2 (Metamitron) Hazard Symbols HarmfulXn,DangerousN
Synonyms

3-Methyl-4-amino-6-phenyl-1,2,4-triazin(4H)-on;4-Amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one;4-Amino-4,5-dihydro-3-methyl-6-phenyl-1,2,4-triazin-5-one;

Article Data 15

Metamitron Synthetic route

1603-79-8

phenylglyoxylic acid ethyl ester

1068-57-1

acetic acid hydrazide

41394-05-2

metamitron

Conditions
ConditionsYield
Stage #1: phenylglyoxylic acid ethyl ester; acetic acid hydrazide In ethanol at 25℃; for 1h;
Stage #2: With ethylenediaminetetraacetic acid In ethanol at 25℃; for 3.33333h; Temperature; Concentration; Further stages;
92%
15206-55-0

methyl 2-oxo-2-phenylacetate

56873-72-4

Acetohydrazid-hydrazon-hydrochlorid

41394-05-2

metamitron

Conditions
ConditionsYield
With triethylamine 1.) CH3OH, 2 h, reflux, 2.) 16 h, room temperature; 1 h, reflux; Yield given. Multistep reaction;
acethydrazidine hydrochloride

acethydrazidine hydrochloride

79848-81-0

N-acetyl-2-oxo-2-phenylacetamide

41394-05-2

metamitron

Conditions
ConditionsYield
With pyridine In methanol; water
In water
611-73-4

Benzoylformic acid

41394-05-2

metamitron

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogenchloride / 4 h / 45 - 60 °C
2: sulfuric acid / methanol / 8 h / 20 - 65 °C
3: hydrazine hydrate / 20 - 25 °C
4: butan-1-ol / 8 h / 20 - 132 °C / Reflux
View Scheme
56735-29-6

C10H12N4O2

41394-05-2

metamitron

Conditions
ConditionsYield
In butan-1-ol at 20 - 132℃; for 8h; Reflux;
613-90-1

benzoyl cyanide

41394-05-2

metamitron

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sulfuric acid / water / 20 - 40 °C
2: hydrogenchloride / 4 h / 45 - 60 °C
3: sulfuric acid / methanol / 8 h / 20 - 65 °C
4: hydrazine hydrate / 20 - 25 °C
5: butan-1-ol / 8 h / 20 - 132 °C / Reflux
View Scheme
15206-55-0

methyl 2-oxo-2-phenylacetate

41394-05-2

metamitron

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid / methanol / 8 h / 20 - 65 °C
2: hydrazine hydrate / 20 - 25 °C
3: butan-1-ol / 8 h / 20 - 132 °C / Reflux
View Scheme
41394-05-2

metamitron

36993-94-9

3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one

Conditions
ConditionsYield
With tert.-butylhydroperoxide; 2,2′-((1E,1′E)-(ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))diphenolmanganese(II) In dichloromethane for 6h; Ambient temperature; further oxidation agents;90%
Stage #1: metamitron With titanium dioxide P25 In water for 0.833333h; Darkness;
Stage #2: With sodium persulfate In water for 1h; pH=6.3; Kinetics; Concentration; Reagent/catalyst; pH-value; UV-irradiation;
41394-05-2

metamitron

A

14331-27-2

1-acetyl-2-benzoylhydrazine

B

36993-94-9

3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one

Conditions
ConditionsYield
With oxygen In water at 19.85℃; for 5h; pH=4 - 9; Quantum yield; Kinetics; Deamination; Photolysis;A 20%
B 80%
41394-05-2

metamitron

36993-94-9

3-Methyl-6-phenyl-1,2,4-triazin-5(2H)-on

Conditions
ConditionsYield
With lead(IV) acetate In dichloromethane; acetic acid for 3h; Ambient temperature;74%

Metamitron Specification

The Metamitron, with the CAS registry number 41394-05-2 and EINECS registry number 255-349-3, has the systematic name of 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one. And the molecular formula of this chemical is C10H10N4O. It belongs to the following product categories: Heterocyclic Compounds; Herbicide; Building Blocks; Heterocyclic Building Blocks; Triazines.

The physical properties of Metamitron are as following: (1)ACD/LogP: 0.83; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.83; (4)ACD/LogD (pH 7.4): 0.83; (5)ACD/BCF (pH 5.5): 2.52; (6)ACD/BCF (pH 7.4): 2.52; (7)ACD/KOC (pH 5.5): 67.37; (8)ACD/KOC (pH 7.4): 67.38; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 48.27 Å2; (13)Index of Refraction: 1.672; (14)Molar Refractivity: 56.17 cm3; (15)Molar Volume: 149.9 cm3; (16)Polarizability: 22.27×10-24cm3; (17)Surface Tension: 55.7 dyne/cm; (18)Density: 1.34 g/cm3; (19)Flash Point: 156.9 °C; (20)Enthalpy of Vaporization: 57.89 kJ/mol; (21)Boiling Point: 335.8 °C at 760 mmHg; (22)Vapour Pressure: 0.000117 mmHg at 25°C.

Uses of Metamitron: It can be used to produce N-acetyl-N'-benzoyl-hydrazine and 3-methyl-6-phenyl-4H-[1,2,4]triazin-5-one. This reaction will need reagent O2, and solvent H2O. The reaction time is 5 hours with temperature of 19.85°C and PH 4-9, and the yield is about 80%.

Metamitron can be used to produce N-acetyl-N'-benzoyl-hydrazine and 3-methyl-6-phenyl-4H-[1,2,4]triazin-5-one

You should be cautious while dealing with this chemical. It is harmful if swallowed, and it is also very toxic to aquatic organisms. Therefore, you had better avoid release to the environment. Refer to special instructions safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2N(/C(=N\N=C2\c1ccccc1)C)N
(2)InChI: InChI=1/C10H10N4O/c1-7-12-13-9(10(15)14(7)11)8-5-3-2-4-6-8/h2-6H,11H2,1H3
(3)InChIKey: VHCNQEUWZYOAEV-UHFFFAOYAW

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 1gm/kg (1000mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A261, Pg. 1983,
mouse LD50 intraperitoneal > 600mg/kg (600mg/kg)   Pesticide Biochemistry and Physiology. Vol. 23, Pg. 123, 1984.
mouse LD50 oral 1450mg/kg (1450mg/kg)   "Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel," Perkow, W., Berlin, Verlag Paul Parey, 1971-1976Vol. -, Pg. -, 1971/1976.
quail LD50 unreported 1930mg/kg (1930mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C156, 1991.
rat LC50 inhalation > 331mg/m3/4H (331mg/m3)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A261, Pg. 1983,
rat LD50 oral 1447mg/kg (1447mg/kg)   "Agricultural Chemicals," Thomson, W.T., 4 vols., Fresno, CA, Thomson Publications, 1976/77 revisionVol. 2, Pg. 133, 1977.
rat LD50 skin > 500mg/kg (500mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A261, Pg. 1983,

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