Hexaconazole ((-)-Hexaconazol)

Hexaconazole is a broad-spectrum triazole fungicide that inhibits ergosterol biosynthesis via inhibition of the cytochrome P450-dependent 14α-demethylation of lanosterol, which results in disruption of the fungal cell membrane and cell death.¹ It is fungicidal against the powdery mildews B. graminis and S. cucurbitae on cucumber plants in a concentration-dependent manner and is curative against powdery mildew on barley plants when used at a concentration of 6.7 mg/L.² It also inhibits growth of R. bataticola and S. rolfsii (ED₅₀s = 6.35 and 1.27 mg/L, respectively).³ Exogenous application of hexaconazole (15 mg/L) to M. chamomilla plants improves water, proline, and protein contents as well as increases non-enzymatic and enzymatic antioxidant and apigenin-7-glucoside content during a water deficit stress tolerance test.⁴ Hexaconazole inhibits the differentiation of mouse embryonic stem cells into cardiomyocytes (EC₅₀ = 16.6 μM).⁵ It also induces bone morphological defects in mouse fetuses when administered to pregnant adult females during gestation.

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.Tsuda, M., Itoh, H., and Kato, S.Evaluation of the systemic activity of simeconazole in comparison with that of other DMI fungicidesPest Manag. Sci.60(9)875-880(2004) 3.Shakil, N.A., Kumar, J., Pandey, A., et al.Synthesis and pesticidal activity of new N-alkyl-N-[1-(2-hydroxyphenyl) ethyl]aminesJ. Environ. Sci. Health B44(4)344-349(2009) 4.Hojati, M., Modarres-Sanavy, S.A.M., Ghanati, F., et al.Hexaconazole induces antioxidant protection and apigenin-7-glucoside accumulation in Matricaria chamomilla plants subjected to drought stressJ. Plant Physiol.168(8)782-791(2011) 5.de Jong, E.G., Barenys, M., Hermsen, S.A.B., et al.Comparison of the mouse embryonic stem cell test, the rat whole embryo culture and the zebrafish embryotoxicity test as alternative methods for developmental toxicity testing of six 1,2,4-triazolesToxicol. Appl. Pharmacol.253(2)103-111(2011)