Metalaxyl-M

Base Information

• Chemical Name: Metalaxyl-M
• CAS No.: 70630-17-0
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.336
• European Community (EC) Number: 615-135-6
• UNII: F1Q54ONN4H
• DSSTox Substance ID: DTXSID8032671
• Nikkaji Number: J1.906B
• Wikidata: Q27128142
• Metabolomics Workbench ID: 61210
• ChEMBL ID: CHEMBL1905521
• Mol file: 70630-17-0.mol

Synonyms:mefenoxam;N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-D-alanine methyl ester

Chemical Property of Metalaxyl-M

Chemical Property:

• Appearance/Colour: light yellow to light brown thick liquid
• Vapor Pressure: 2E-06mmHg at 25°C
• Melting Point: 38.7oC
• Refractive Index: 1.527
• Boiling Point: 394.3 °C at 760 mmHg
• PKA: 1.41±0.50(Predicted)
• Flash Point: 192.3 °C
• PSA: 55.84000
• Density: 1.117 g/cm³
• LogP: 1.84430
• Storage Temp.: 0-6°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 279.14705815
• Heavy Atom Count: 20
• Complexity: 335

Purity/Quality:

99% ^*data from raw suppliers

Metalaxyl-M ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39-46

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)C)N(C(C)C(=O)OC)C(=O)COC
• Isomeric SMILES: CC1=C(C(=CC=C1)C)N([C@H](C)C(=O)OC)C(=O)COC
• Description: Metalaxyl-M is the more active of the two enantiomers of the phenylamide fungicide metalaxyl; metalaxyl is currently registered in more than 80 countries with uses on more than 60 crops. 1996 Mefenoxam (metalaxyl-M) first registered for use in NYS. Metalaxyl-M is the first enantiomeric form of a fungicide introduced into the market. When used as seed-treatment, soil treatment or foliar application against fungi of the order Peronosporales, it provides the same excellent level of efficacy as metalaxyl but at half the application rate. Mefenoxam is more commonly used than metalaxyl in most pesticide products registered in NYS today.
• Uses: Metalaxyl-M is an isomer of Metalaxyl (M258740), an agricultural fungicide. Phenylamide fungicide or use in food crops, shrubs and turf.

Technology Process of Metalaxyl-M

There total 12 articles about Metalaxyl-M which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

Methoxyacetyl chloride (38870-89-2) + methyl (2R)-2-[(2,6-dimethylphenyl)amino]propanoate (57646-33-0) → methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-D-alaninate (57837-19-1,69516-34-3,70630-17-0)

Guidance literature:

With sodium hydrogencarbonate; In toluene; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.tetasy.2005.01.033

Reference yield:

methyl (2R)-2-[(2,6-dimethylphenyl)amino]propanoate (57646-33-0) + 2-methoxyacetic acid (625-45-6) → methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-D-alaninate (57837-19-1,69516-34-3,70630-17-0)

Guidance literature:

silica gel; In diethylene glycol diethyl ether; at 198 ℃; for 40h; Product distribution / selectivity;

Reference yield:

methyl-N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate (57837-19-1) → methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-D-alaninate (57837-19-1,69516-34-3,70630-17-0) + D,L-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-alanine methyl ester

Guidance literature:

With nanocellulose derivative/silica hybrid core-shell slurry-packed stainless steel column; In water; acetonitrile; at 25 ℃; Solvent; Reagent/catalyst; Resolution of racemate;

DOI:10.3390/molecules21050561

upstream raw materials:

Methoxyacetyl chloride

methyl N-(2,6-dimethylphenyl)alaninate

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

2-ethoxyethyl N-(2,6-dimethylphenyl)alaninate

Refernces

• 1、 Lei, Shuo,Li, Xianhui,Wang, Yang,Sun, Lirong,Liu, Hao,Zhao, Longshan. "Synthesis of magnetic multiwall carbon nanotubes for enantioseparation of three pesticide residues in fruits and vegetables by chiral liquid chromatography". . p. 1321 - 1329. Retrieved 2018/11/03.
• 2、 Li, Qing,Hou, Chuan-Jin,Liu, Xiao-Ning,Huang, De-Zhi,Liu, Yan-Jun,Yang, Rui-Feng,Hu, Xiang-Ping. "Chiral phosphine-phosphoramidite ligands for highly enantioselective hydrogenation of N-arylimines". . p. 13702 - 13708. Retrieved 2015/02/19.