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Metalaxyl
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Name

Metalaxyl

 EINECS 260-979-7
CAS No. 57837-19-1 Density 1.117 g/cm3
PSA 55.84000 LogP 1.84430
Solubility 0.84 g/100 mL in water Melting Point 72-73 °C
Formula C15H21NO4 Boiling Point 394.3 °C at 760 mmHg
Molecular Weight 279.336 Flash Point 192.3 °C
Transport Information UN 1648 3/PG 2 Appearance Colorless, odorless crystal
Safety 13-24-37-46-61-36-26-16 Risk Codes 22-43-52/53-36-20/21/22-11
Molecular Structure Molecular Structure of 57837-19-1 (Metalaxyl) Hazard Symbols HarmfulXn, FlammableF
Synonyms

Apron;Apron TL;Metaxanin;EPA Pesticide Chemical Code 113501;Alanine,N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-,methyl ester;Ridomil 72WP;N-(2,6-Dimethylphenyl)-N-(methoxyacetyl)-alanine methyl ester;102256-63-3;Ridomil Vino;Methyl N-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate;Apron 2E;CG 117;Metasyl;Metaxanine;Ridomil;Methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninate;DL-Alanine, N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-, methyl ester (9CI);Ridomil 2E;Metanaxin;Apron FL;CGA 48988;Apron SD 35;IPO-FS;Subdue 2E;Jiashuangling;Subdue;Alanine, N-(methoxyacetyl)-N-(2,6-xylyl)-, methyl ester, DL-;Allegiance;Metalaxil;Subdue 5SP;Span;Metalaxy-M;

Article Data 17

Metalaxyl Synthetic route

38870-89-2

Methoxyacetyl chloride

57646-33-0

methyl (2R)-2-[(2,6-dimethylphenyl)amino]propanoate

57837-19-1

methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate

Conditions
ConditionsYield
In toluene for 2.5h; Reflux;88.2%
67-56-1

methanol

52888-51-4

methyl 2-[N-(2,6-dimethylphenyl)-N-(chloroacetyl)-amino]-propionate

57837-19-1

methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate

38870-89-2

Methoxyacetyl chloride

52888-49-0

methyl N-(2,6-dimethylphenyl)alaninate

57837-19-1

methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate

Conditions
ConditionsYield
In water
5445-17-0

Methyl 2-bromopropionate

53823-88-4

N-(1-methoxyacetyl)-2,6-dimethylaniline

A

N-methoxyacetyl-2,6-dimethylaniline sodium salt

B

57837-19-1

methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate

Conditions
ConditionsYield
With sodium methylate In 5,5-dimethyl-1,3-cyclohexadiene
81803-98-7

N-(1'methoxycarbonylethyl)-N-methoxyacetyl-2,6-dimethyl-3-aminoaniline

77152-08-0

trifluoromethylcopper(I)

A

methyl 2-(N-(2,6-dimethyl-3-(trifluoromethyl)phenyl)-2-methoxyacetamido)propanoate

B

57837-19-1

methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate

Conditions
ConditionsYield
Stage #1: N-(1'methoxycarbonylethyl)-N-methoxyacetyl-2,6-dimethyl-3-aminoaniline With hydrogen fluoride; sodium nitrite In water; acetonitrile at 0℃; Inert atmosphere;
Stage #2: trifluoromethylcopper(I) In water; N,N-dimethyl-formamide; acetonitrile at 0℃; for 0.25h; Inert atmosphere; Overall yield = 75 %Spectr.;
57837-19-1

methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate

4-carbaldehydebutyryl chloride

C19H25NO6

Conditions
ConditionsYield
Stage #1: 4-carbaldehydebutyryl chloride With aluminum (III) chloride In 1,2-dichloro-ethane at 20℃; for 3h;
Stage #2: methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate In 1,2-dichloro-ethane for 4h; Reflux;		89.7%
677-25-8

ethylenesulfonyl fluoride

57837-19-1

methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate

methyl (E)-N-(4-(2-(fluorosulfonyl)vinyl)-2,6-dimethylphenyl)-N-(2-methoxyacetyl)alaninate

Conditions
ConditionsYield
With 5-(perfluoroethyl)-3-(trifluoromethyl)pyridine-2-ol; silver(I) acetate; palladium diacetate at 100℃; for 24h; Sealed tube; regioselective reaction;51%
57837-19-1

methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate

N-(2-carboxy-6-methylphenyl)-N-(methyloxyacetyl)alanine methyl ester

Conditions
ConditionsYield
With pyridine; potassium permanganate In water at 70℃;5%
With pyridine; potassium permanganate at 70℃;
57837-19-1

methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate

rac-2-[(2,6-dimethylphenyl)methoxyacetylamino]propionic acid

Conditions
ConditionsYield
With potassium hydroxide at 110 - 115℃; for 1h; Heating;
With sulfuric acid for 10h; Heating;
Stage #1: methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate With potassium hydroxide at 110 - 115℃; for 1h;
Stage #2: With hydrogenchloride Further stages.;
57837-19-1

methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate

mercury dichloride

116613-47-9

mercury(II)chloride*methyl N-(2,6-dimethylphenyl)-N-(2-methoxyacetyl)alaninate

Conditions
ConditionsYield
In ethanol stoich. amts. mixing, heating on water bath, stirring, 30 min.; partial distn., cooling, detected by elem. anal.;

Metalaxyl Chemical Properties

IUPAC Name: methyl 2-(N-(2-methoxyacetyl)-2,6-dimethylanilino)propanoate 
Empirical Formula: C15H21NO4
Molecular Weight: 279.3315g/mol
EINECS: 260-979-7 
Structure of Metalaxyl (CAS NO.57837-19-1):

Index of Refraction: 1.527
Molar Refractivity: 76.88 cm3
Molar Volume: 249.8 cm3
Polarizability: 30.48×10-24cm3
Surface Tension: 40.5 dyne/cm
Density: 1.117 g/cm3
Flash Point: 192.3 °C
Enthalpy of Vaporization: 64.43 kJ/mol 
Melting point: 72-73 ºC
Boiling Point: 394.3 °C at 760 mmHg
Vapour Pressure: 2E-06 mmHg at 25°C 
Water solubility: 0.84 g/100 mL 
Product Categories: FUNGICIDE;Amide structureMethod Specific;Endocrine Disruptors (Draft)Alphabetic;EPA;Fungicides;M;META - METH;Pesticides 
Canonical SMILES: CC1=C(C(=CC=C1)C)N(C(C)C(=O)OC)C(=O)COC
InChI: InChI=1S/C15H21NO4/c1-10-7-6-8-11(2)14(10)16(13(17)9-19-4)12(3)15(18)20-5/h6-8,12H,9H2,1-5H3
InChIKey: ZQEIXNIJLIKNTD-UHFFFAOYSA-N

Metalaxyl Uses

 Metalaxyl (CAS NO.57837-19-1) can be used to control Pythium in a number of vegetable crops, and Phytophthora in peas.

Metalaxyl Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 566mg/kg (566mg/kg)   Journal of Hygiene, Epidemiology, Microbiology, and Immunology. Vol. 35, Pg. 375, 1991.
rat LD50 skin > 3100mg/kg (3100mg/kg)   Pesticide Manual. Vol. 9, Pg. 554, 1991.

Metalaxyl Safety Profile

Hazard Codes: HarmfulXn,FlammableF
Risk Statements: 22-43-52/53-36-20/21/22-11
R22:Harmful if swallowed. 
R43:May cause sensitization by skin contact. 
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R11:Highly flammable.
Safety Statements: 13-24-37-46-61-36-26-16 
S13:Keep away from food, drink and animal foodstuffs. 
S24:Avoid contact with skin. 
S37:Wear suitable gloves. 
S46:If swallowed, seek medical advice immediately and show this container or label. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets. 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S16:Keep away from sources of ignition.
RIDADR: UN 1648 3/PG 2
RTECS: AY6910000
Hazardous Substances Data 57837-19-1(Hazardous Substances Data)
Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx.

Metalaxyl Specification

  Metalaxyl ,  its cas register number is 57837-19-1. It also can be called Allegiance ; Apron ; Apron SD 35 ; Caswell No. 375AA ; D,L-N-(2,6-Dimethylphenyl)-N-(2'-methoxyacetyl)alaninate de methyle ; Metalaxil ; Metanaxin ; Methyl N-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate ; N-(2,6-Dimethylphenyl)-N-(methoxyacetyl)-alanine methyl ester ; Ridomil ;
 Subdue .

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 71 deg C   EXP
Boiling Point 295.9 dec deg C   EXP
log P (octanol-water) 1.65 (none)   EXP
Water Solubility 8400 mg/L 22 EXP
Vapor Pressure 5.62E-06 mm Hg 25 EXP
Henry's Law Constant 2.95E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.69E-11 cm3/molecule-sec 25 EST


 

 

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