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| Names | |
|---|---|
| IUPAC name Methyl 2-[N-(2,6-dimethylphenyl)(methoxy)acetamido]propanoate | |
| Other names MethylN-(2,6-dimethylphenyl)-N-(2-methoxyacetyl)alaninate | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.055.418 |
| EC Number |
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| KEGG |
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| UNII | |
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| Properties | |
| C15H21NO4 | |
| Molar mass | 279.33 g/mol |
| Appearance | Fine white powder |
| Density | 1.20g/cm3 at 20 °C |
| Melting point | 71 to 72 °C (160 to 162 °F; 344 to 345 K)[2] |
| Boiling point | 295.9 °C (564.6 °F; 569.0 K) at 760 mm Hg |
| 8,400 mg/L at 22 °C | |
| logP | 1.65 (octanol/water)[1] |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Metalaxyl is an acylalaninefungicide withsystemic function.[3] Its chemical name is methyl N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate. It can be used to controlPythium in a number ofvegetable crops, andPhytophthora inpeas. Metalaxyl-M is the ISO common name[4] and Ridomil Gold is the trade name for the optically pure (-) / D / R active stereoisomer, which is also known asmefenoxam.[5]
It is the active ingredient in the seed treatment agentApron XL LS.[6]
The fungicide has suffered severeresistance problems. The fungicide wasmarketed for use againstPhytophthora infestans. However, in the summer of 1980, in theRepublic of Ireland, the crop was devastated by a potato blight epidemic after a resistantrace of theoomycete appeared.[7] Irishfarmers later successfullysued the company for their losses.[citation needed]Maximum pesticide residue limits for the EU/UK are set at 0.5 mg/kg for oranges and 1.0 mg/kg for apples.[citation needed] As early as 1998Pythium was known to be widely developing resistance to metalaxyl[8] which was the most effective control at the time.[8] VariousPythium populations have been known to have resistance to mefenoxam since the 1980s[9] and metalaxyl since 1984.[10] There is wide variability in resistance/sensitivity betweenPythium species, with some populations showing complete ineffectiveness.[9]
The first synthesis of metalaxyl was disclosed in patents filed byCiba Geigy.[11]
2,6-Xylidine isalkylated with methyl 2-bromopropionate to give analanine derivative. This is further reacted with theacid chloride ofmethoxyacetic acid to yieldracemic metalaxyl.[11][12] Thehomochiral, single-isomer version of the chemical, which retains all its fungicidal activity, has been manufactured.[13]
