1-[[2-(2,4-dichlorophenyl)-4-(1,1,2,2,3,3,3-heptadeuteriopropyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole

Uses

Labelled Propiconazole (P770100). Systemic foliar fungicide. Agricultural fungicide.

Biological Activity

Propiconazole-d7 is intended for use as an internal standard for the quantification of propiconazole by GC- or LC-MS. Propiconazole is a broad-spectrum triazole fungicide that inhibits the conversion of lanosterol to ergosterol, leading to fungal cell membrane disruption.1 It inhibits S. cerevisiae, but not rat liver, microsomal cytochrome P450 (IC50s = 0.04 and >200 μM, respectively).2 Propiconazole inhibits the growth of T. deformans and R. stolonifer (EC50s = 0.073 and 4.6 μg/ml, respectively), as well as A. niger, M. fructigena, S. nodorum, T. harzanium, R. solani, and S. rolfsii at concentrations ranging from 0.1 to 5 ppm.3 It increases the weight of seminal vesicles and vas deferens, as well as the percentage of sperm with abnormal tail morphology, and decreases the plasma concentration of estradiol in male rats when administered at a dose of 4 mg/kg.4 Propiconazole increases production of reactive oxygen species (ROS), the number of DNA mutations, and the incidence of tumor formation in mouse liver.5 Formulations containing propiconazole have been used in the control of fungi in agriculture.

References

1.Zarn, J.A., Brüschweiler, B.J., and Schlatter, J.R.Azole fungicides affect mammalian steroidogenesis by inhibiting sterol 14 α-demethylase and aromataseEnviron. Health Perspect.111(3)255-261(2003) 2.Vanden Bossche, H., Lauwers, W., Willemsens, G., et al.Molecular basis for the antimycotic and antibacterial activity of N-substituted imidazoles and triazoles: The inhibition of isoprenoid biosynthesisPestic. Sci.15(2)188-198(1984) 3.Sancholle, M., Weete, J.D., and Montani, C.Effects of triazoles on fungi: I. Growth and cellular permeabilityPest. Biochem. Phys.21(1)31-44(1984) 4.Costa, N.O., Vieira, M.L., Sgarioni, V., et al.Evaluation of the reproductive toxicity of fungicide propiconazole in male ratsToxicology33555-61(2015) 5.Nesnow, S.Integration of toxicological approaches with "omic" and related technologies to elucidate mechanisms of carcinogenic action: Propiconazole, an exampleCancer Lett.334(1)20-27(2013)