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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:8489 ;
ChEMBL	ChEMBL560579 ;
ChemSpider	39402 ;
ECHA InfoCard	100.056.441
KEGG	C11121 ;
PubChem CID	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, 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

↑ Merck Index, 11th Edition, 7830.
↑ EXTOXNET
↑ See entry for Complete Wood Preservative
↑ L. Toribio, M. J. del Nozal, J. L. Bernal, J. J. Jeménez und C. Alonso, J. Chromatography A 2004, 1046, 249-253.
↑ W. T. Thomson. 1997. Agricultural Chemicals. Book IV: Fungicides. 12th edition. Thomson Publications, Fresno, CA
↑ 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)

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[1] Merck Index, 11th Edition, 7830.

[2] EXTOXNET

[3] See entry for Complete Wood Preservative

[Toribio-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