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Fungicides
Metalaxyl
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Metalaxyl

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Metalaxyl
Metalaxyl.svg
Metalaxyl 3D BS.png
Names
IUPAC name
methyl 2-[(2,6-dimethylphenyl)(methoxyacetyl)amino]propanoate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.055.418
EC Number
  • 260-979-7
KEGG
PubChem CID
UNII
  • 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 ☒N
    Key: ZQEIXNIJLIKNTD-UHFFFAOYSA-N ☒N
  • InChI=1/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
    Key: ZQEIXNIJLIKNTD-UHFFFAOYAF
  • COCC(=O)N(c1c(C)cccc1C)C(C)C(=O)OC
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)
Boiling point 295.9 °C (564.6 °F; 569.0 K) at 760 mm Hg
8,400 mg/L at 22 °C
log P 1.65 (octanol/water)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Metalaxyl is an acylalanine fungicide with systemic function. Its chemical name is methyl N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate. It can be used to control Pythium in a number of vegetable crops, and Phytophthora in peas. Metalaxyl-M is the ISO common name and Ridomil Gold is the trade name for the optically pure (-) / D / R active stereoisomer, which is also known as mefenoxam.

It is the active ingredient in the seed treatment agent Apron XL LS.

The fungicide has suffered severe resistance problems. The fungicide was marketed for use against Phytophthora infestans. However, in the summer of 1980, in the Republic of Ireland, the crop was devastated by a potato blight epidemic after a resistant race of the oomycete appeared. Irish farmers later successfully sued the company for their losses. Maximum pesticide residue limits for the EU/UK are set at 0.5 mg/kg for oranges and 1.0 mg/kg for apples. As early as 1998 Pythium was known to be widely developing resistance to metalaxyl which was the most effective control at the time. Various Pythium populations have been known to have resistance to mefenoxam since the 1980s and metalaxyl since 1984. There is wide variability in resistance/sensitivity between Pythium species, with some populations showing complete ineffectiveness.

External links

  • Metalaxyl in the Pesticide Properties DataBase (PPDB)
  • Metalaxyl-M in the Pesticide Properties DataBase (PPDB)



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