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).
checkY verify (what is checkY☒N ?)
Infobox references

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.

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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