Metalaxyl

Metalaxyl
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
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)[1]
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)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Metalaxyl is an acylalanine fungicide with systemic function.[3] 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 or Ridomil Gold are trade names for the optically pure (-) / D / R active stereoisomer, which is also known as Mefenoxam.[4]

It is the active ingredient in the seed treatment agent Apron XL LS.[5]

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.[6] 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

References

  1. ↑ O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1058
  2. ↑ Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 134
  3. ↑ Sukul, P; Spiteller, M (2000). "Metalaxyl: persistence, degradation, metabolism, and analytical methods". Reviews of environmental contamination and toxicology. 164. PMID 12587832.
  4. ↑ Monkiedje, Adolphe; Spiteller, Michael (2002). "Effects of the phenylamide fungicides, mefenoxam and metalaxyl, on the microbiological properties of a sandy loam and a sandy clay soil". Biology and Fertility of Soils. 35 (6). doi:10.1007/s00374-002-0485-1.
  5. ↑ "bmz10s02.pdf" (PDF). Government of Manitoba. Archived from the original (PDF) on 2007-09-30.
  6. ↑ Working on potato blight in Northern Ireland
  • Metalaxyl in the Pesticide Properties DataBase (PPDB)
  • Metalaxyl-M in the Pesticide Properties DataBase (PPDB)


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