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
ChEBI	CHEBI:8489
ChEMBL	ChEMBL560579
ChemSpider	39402
Jmol interactive 3D	Image
KEGG	C11121
PubChem	43234
UNII	142KW8TBSR
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 Key: STJLVHWMYQXCPB-UHFFFAOYSA-N 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
SMILES 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
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

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, mushrooms, corn, wild rice, peanuts, almonds, sorghum, oats, pecans, apricots, peaches, nectarines, plums and prunes.^[2] 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)