Detail of "6890-88-6"

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The discovery and mode of action of PP450, a new broad spectrum fungicide for cereals

The discovery and mode of action of PP450, a new broad spectrum fungicide for cereals. Baldwin, B. C.; Wiggins, T. E.; Marchington, A. F.; Worthington, P. A. (Plant Prot. Div., ICI PLC, Bracknell RG 12 6EY, UK). Meded. Fac. Landbouwwet., Rijksuniv. Gent, 49(2a), 303-10 (English) 1984. CODEN: MFLRA3. ISSN: 0368-9697. DOCUMENT TYPE: Journal CA Section: 5 (Agrochemical Bioregulators) The azole type of systemic fungicides bind to the Fe atom of the cytochrome P 450 involved in the 14-demethylase of ergosterol [57-87-4] biosynthesis. Modeling the active site of the enzyme by computer graphics and comparison of the lanosterol substrate of the reaction with diclobutrazol indicates how inhibitors bind. The fungicide PP450 (2,4'-difluoro-a(1H-1,2,4-triazol-1-ylmethyl)benzhydryl alc.)(flutriafol) [87676-93-5] fits the above model. PP450 is a potent inhibitor of the 14a-demethylase enzyme, and binds strongly to a partially purified cytochrome P 450 from yeast. It blocks ergosterol biosynthesis in Ustilago maydis in vitro, leading to a decrease in ergosterol content and an accumulation of 24-methylene-24,25-dihydrolanosterol [6890-88-6] and other 14-Me sterols. The change in sterols leads to a loss of membrane function. The compd. showed a broad spectrum of systemic activity against cereal diseases. As a spray (125 g/ha) it controlled Erysiphe graminis, Puccinia, Septoria, and Rhynchosporium secalis. Seed treatment at 75 ppm controlled seed-borne and soil diseases and at higher rates it was active against foliar diseases.

Biochemical effects of miconazole on fungi

Biochemical effects of miconazole on fungi. II. Inhibition of ergosterol biosynthesis in Candida albicans. Van den Bossche, H.; Willemsens, G.; Cools, W.; Lauwers, W. F. J.; Le Jeune, L. (Anal. Dep., Janssen Pharm., Beerse, Belg.). Chem.-Biol. Interact., 21(1), 59-78 (English) 1978. CODEN: CBINA8. ISSN: 0009-2797. DOCUMENT TYPE: Journal CA Section: 3 (Biochemical Interactions) The effects of the antifungal agent miconazole nitrate (I nitrate) [22832-87-7] on the ergosterol [57-87-4] biosynthesis in C. albicans were investigated after in vitro contact with the drug for 1, 4, 16, and 24 h. A time- and dose-(2 ′ 10-10-10-4M) dependent inhibition of acetate-14C incorporation into ergosterol was obsd. Fifty percent inhibition of the acetate incorporation into ergosterol was found after 1 h incubation in the presence of 10-9M I. Simultaneously 24-methylenedihydrolanosterol [6890-88-6], lanosterol [79-63-0], obtusifoliol [16910-32-0], 4,14-dimethylzymosterol [21080-46-6], and 14-methylfecosterol [33886-74-7] accumulated. I also intervened to a small extent in triglyceride synthesis. However, in all circumstances studied, ergosterol biosynthesis was affected at lower doses than those interfering with the acetate incorporation into triglycerides. Sixteen and 24 h of incubation in the presence of I (310-6M) also increased fatty acid synthesis. I-induced inhibition of the C-14 sterol demethylation may be at the origin of the previously obsd. permeability changes in I-treated C. albicans.