Propiconazole

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.

Propiconazole[1]
Names
IUPAC name
1-[ [2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.056.441
KEGG
UNII
  • 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
C15H17Cl2N3O2
Molar mass 342.22038
Boiling point 180 °C (356 °F; 453 K) at 0.1 mmHg
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

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
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