Metalaxyl

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Metalaxyl
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Names
IUPAC name
Methyl 2-[N-(2,6-dimethylphenyl)(methoxy)acetamido]propanoate
Other names
Methyl N-(2,6-dimethylphenyl)-N-(2-methoxyacetyl)alaninate
Identifiers
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3D model (JSmol)
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  • 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 checkY
    Key: ZQEIXNIJLIKNTD-UHFFFAOYSA-N checkY
  • 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)[2]
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)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Template:Chembox Footer/trackingTemplate:Short description

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 Page Template:Visible anchor/styles.css has no content.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]

Synthesis

The first synthesis of metalaxyl was disclosed in patents filed by Ciba Geigy.[11]

2,6-Xylidine is alkylated with methyl 2-bromopropionate to give an alanine derivative. This is further reacted with the acid chloride of methoxyacetic acid to yield racemic metalaxyl.[11][12] The homochiral, single-isomer version of the chemical, which retains all its fungicidal activity, has been manufactured.[13]

References

  1. ^ Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 134
  2. ^ 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
  3. ^ Page Module:Citation/CS1/styles.css has no content.Sukul, P; Spiteller, M (2000). "Metalaxyl: persistence, degradation, metabolism, and analytical methods". Reviews of Environmental Contamination and Toxicology. 164: 1–26. PMID 12587832.
  4. ^ Page Module:Citation/CS1/styles.css has no content."Compendium of Pesticide Common Names: metalaxyl". BCPC.
  5. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content."bmz10s02.pdf" (PDF). Government of Manitoba. Archived from the original (PDF) on 2007-09-30.
  7. ^ Working on potato blight in Northern Ireland
  8. ^ a b Page Module:Citation/CS1/styles.css has no content."Survey of Pythium Isolates for Resistance to Subdue (metalaxyl)" (PDF). UMass Amherst. Retrieved 2020-11-23.
  9. ^ a b Page Module:Citation/CS1/styles.css has no content.Del Castillo Múnera, Johanna; Hausbeck, Mary K. (2016). "Characterization of Pythium Species Associated With Greenhouse Floriculture Crops in Michigan". Plant Disease. 100 (3). American Phytopathological Society: 569–576. doi:10.1094/pdis-03-15-0296-re. ISSN 0191-2917. PMID 30688597.
  10. ^ Page Module:Citation/CS1/styles.css has no content.Sanders, P. L. (1984). "Failure of Metalaxyl to Control Pythium Blight on Turfgrass in Pennsylvania". Plant Disease. 68 (1). American Phytopathological Society: 776. doi:10.1094/pd-68-776. ISSN 0191-2917.
  11. ^ a b Page Template:Citation/styles.css has no content.GB patent 1500581, "Substituted amides and their use as fungicides", issued Script error: No such module "auto date formatter"., assigned to Ciba-Geigy AG 
  12. ^ Page Module:Citation/CS1/styles.css has no content.Ishitani, Haruro; Yu, Zhibo; Ichitsuka, Tomohiro; Koumura, Nagatoshi; Onozawa, Shun-ya; Sato, Kazuhiko; Kobayashi, Shū (2022). "Two-Step Continuous-Flow Synthesis of Fungicide Metalaxyl through Catalytic C−N Bond-Formation Processes". Advanced Synthesis & Catalysis. 364: 18–23. doi:10.1002/adsc.202100898.
  13. ^ Page Module:Citation/CS1/styles.css has no content.Blaser, Hans-Ulrich; Spindler, Felix (1997). "Enantioselective catalysis for agrochemicals. The case histories of (S)–metolachlor, (R)–metalaxyl and clozylacon". Topics in Catalysis. 4 (3/4): 275–282. doi:10.1023/A:1019164928084.
  • Metalaxyl in the Pesticide Properties DataBase (PPDB)
  • Metalaxyl-M in the Pesticide Properties DataBase (PPDB)


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