Metalaxyl

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Metalaxyl
IUPAC name

2-[(2,6-dimethylphenyl)- (2-methoxy-1-oxoethyl) amino]propanoic
acid methyl ester

Identifiers
CAS number 57837-19-1 YesY
PubChem 42586
ChEMBL CHEMBL105809 N
Jmol-3D images Image 1
Properties
Molecular formula C15H21NO4
Molar mass 279.33 g/mol
Appearance Fine white powder
Density 1.20g/cm3 at 20 °C
Melting point 71-72 °C[1]
Boiling point 295.9 °C at 760 mm Hg
Solubility in water 8,400 mg/L at 22 °C
log P 1.65 (octanol/water)[2]
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Metalaxyl is a phenylamide 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 trade name of the optically pure stereoisomer.

It is the active ingredient in the seed treatment agent Apron XL LS.[3]

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.[4] Irish farmers later successfully sued 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

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. ↑ http://www.gov.mb.ca/agriculture/crops/vegetablecrops/pdf/bmz10s02.pdf
  4. ↑ Working on potato blight in Northern Ireland
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