Propiconazole

Propiconazole[1]
Names
IUPAC name
1-[ [2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole
Identifiers
CAS Number
  • 60207-90-1 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:8489 checkY
ChEMBL
  • ChEMBL560579 checkY
ChemSpider
  • 39402 checkY
ECHA InfoCard 100.056.441 Edit this at Wikidata
KEGG
  • C11121 checkY
PubChem CID
  • 43234
UNII
  • 142KW8TBSR checkY
CompTox Dashboard (EPA)
  • DTXSID8024280 Edit this at Wikidata
InChI
  • InChI=1S/C15H17Cl2N3O2/c1-2-3-12-7-21-15(22-12,8-20-10-18-9-19-20)13-5-4-11(16)6-14(13)17/h4-6,9-10,12H,2-3,7-8H2,1H3 checkY
    Key: STJLVHWMYQXCPB-UHFFFAOYSA-N checkY
  • InChI=1/C15H17Cl2N3O2/c1-2-3-12-7-21-15(22-12,8-20-10-18-9-19-20)13-5-4-11(16)6-14(13)17/h4-6,9-10,12H,2-3,7-8H2,1H3
    Key: STJLVHWMYQXCPB-UHFFFAOYAJ
  • Clc1ccc(c(Cl)c1)C2(OCC(O2)CCC)Cn3ncnc3
Properties
Chemical formula
 C15H17Cl2N3O2
Molar mass 342.22038
Boiling point 180 °C (356 °F; 453 K) at 0.1 mmHg [1]
Solubility in water
 100 ppm at 20 °C
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
Chemical compound

Propiconazole is a triazole fungicide, also known as a DMI, or demethylation inhibiting fungicide due to its binding with and inhibiting the 14-alpha demethylase enzyme from demethylating a precursor to ergosterol. Without this demethylation step, the ergosterols are not incorporated into the growing fungal cell membranes, and cellular growth is stopped.[citation needed]

Agriculture

Propiconazole is used agriculturally as a systemic fungicide on turfgrasses grown for seed and aesthetic or athletic value, wheat, mushrooms, corn, wild rice, peanuts, almonds, sorghum, oats, pecans, apricots, peaches, nectarines, plums, prunes[2] and lemons. It is also used in combination with permethrin in formulations of wood preserver.[3] Propiconazole is a mixture[4] of four stereoisomers and was first developed in 1979 by Janssen Pharmaceutica.[5] Propiconazole exhibits strong anti-feeding properties against the keratin-digesting Australian carpet beetle Anthrenocerus australis.[6]

References

  1. ^ Merck Index, 11th Edition, 7830.
  2. ^ EXTOXNET
  3. ^ See entry for Complete Wood Preservative
  4. ^ L. Toribio, M. J. del Nozal, J. L. Bernal, J. J. Jeménez und C. Alonso, J. Chromatography A 2004, 1046, 249-253.
  5. ^ W. T. Thomson. 1997. Agricultural Chemicals. Book IV: Fungicides. 12th edition. Thomson Publications, Fresno, CA
  6. ^ Sunderland, M. R.; Cruickshank, R. H.; Leighs, S. J. (2014). "The efficacy of antifungal azole and antiprotozoal compounds in protection of wool from keratin-digesting insect larvae". Textile Research Journal 84 (9): 924–931. http://trj.sagepub.com/content/84/9/924

External links

  • Non-CCA Wood Preservatives: Guide to Selected Resources - National Pesticide Information Center
  • Propiconazole in the Pesticide Properties DataBase (PPDB)