Metalaxyl

Last updated
Metalaxyl
Metalaxyl.svg
Metalaxyl 3D BS.png
Names
IUPAC name
Methyl 2-[N-(2,6-dimethylphenyl)(methoxy)acetamido]propanoate
Other names
Methyl N-(2,6-dimethylphenyl)-N-(2-methoxyacetyl)alaninate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.055.418 OOjs UI icon edit-ltr-progressive.svg
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 X mark.svgN
    Key: ZQEIXNIJLIKNTD-UHFFFAOYSA-N X mark.svgN
  • 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
AppearanceFine 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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 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 as mefenoxam. [5]

It is the active ingredient in the seed treatment agent Apron XL LS. [6]

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. [7] 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.[ citation needed ] As early as 1998 Pythium was known to be widely developing resistance to metalaxyl [8] which was the most effective control at the time. [8] Various Pythium 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 between Pythium species, with some populations showing complete ineffectiveness. [9]

Related Research Articles

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<i>Phytophthora infestans</i> Species of single-celled organism

Phytophthora infestans is an oomycete or water mold, a fungus-like microorganism that causes the serious potato and tomato disease known as late blight or potato blight. Early blight, caused by Alternaria solani, is also often called "potato blight". Late blight was a major culprit in the 1840s European, the 1845–1852 Irish, and the 1846 Highland potato famines. The organism can also infect some other members of the Solanaceae. The pathogen is favored by moist, cool environments: sporulation is optimal at 12–18 °C (54–64 °F) in water-saturated or nearly saturated environments, and zoospore production is favored at temperatures below 15 °C (59 °F). Lesion growth rates are typically optimal at a slightly warmer temperature range of 20 to 24 °C.

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Pythium is a genus of parasitic oomycetes. They were formerly classified as fungi. Most species are plant parasites, but Pythium insidiosum is an important pathogen of animals, causing pythiosis. The feet of the fungus gnat are frequently a vector for their transmission.

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<i>Phytophthora capsici</i> Species of single-celled organism

Phytophthora capsici is an oomycete plant pathogen that causes blight and fruit rot of peppers and other important commercial crops. It was first described by L. Leonian at the New Mexico State University Agricultural Experiment Station in Las Cruces in 1922 on a crop of chili peppers. In 1967, a study by M. M. Satour and E. E. Butler found 45 species of cultivated plants and weeds susceptible to P. capsici In Greek, Phytophthora capsici means "plant destroyer of capsicums". P. capsici has a wide range of hosts including members of the families Solanaceae and Cucurbitaceae as well as Fabaceae.

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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: 1–26. PMID   12587832.
  4. "Compendium of Pesticide Common Names: metalaxyl". BCPC.
  5. 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): 393–398. doi:10.1007/s00374-002-0485-1. S2CID   22642870.
  6. "bmz10s02.pdf" (PDF). Government of Manitoba. Archived from the original (PDF) on 2007-09-30.
  7. Working on potato blight in Northern Ireland
  8. 1 2 "Survey of Pythium Isolates for Resistance to Subdue (metalaxyl)" (PDF). UMass Amherst . Retrieved 2020-11-23.
  9. 1 2 Del Castillo Múnera, Johanna; Hausbeck, Mary K. (2016). "Characterization of Pythium Species Associated With Greenhouse Floriculture Crops in Michigan". Plant Disease . American Phytopathological Society. 100 (3): 569–576. doi: 10.1094/pdis-03-15-0296-re . ISSN   0191-2917. PMID   30688597.
  10. Sanders, P. L. (1984). "Failure of Metalaxyl to Control Pythium Blight on Turfgrass in Pennsylvania". Plant Disease . American Phytopathological Society. 68 (1): 776. doi:10.1094/pd-68-776. ISSN   0191-2917.