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Research Article

Pyrazolo[3,4-c]isothiazole and isothiazolo[4,3-d]isoxazole derivatives as antifungal agents

, , , &
Pages 545-552 | Received 30 Jul 2010, Accepted 22 Sep 2010, Published online: 09 Mar 2011

Figures & data

Figure 1.  Structures of pyrazolo[3,4-c]isothiazole and isothiazolo[4,3-d]isoxazole derivatives (5a–g, 6).

Figure 1.  Structures of pyrazolo[3,4-c]isothiazole and isothiazolo[4,3-d]isoxazole derivatives (5a–g, 6).

Scheme 1.  Synthesis of new pyrazolo[3,4-c]isothiazole derivatives.

Scheme 1.  Synthesis of new pyrazolo[3,4-c]isothiazole derivatives.

Figure 2.  Antifungal activity of the compounds 5a-g and 6 expressed as percentage inhibition of growth on test organisms. The fungi were cultured on PDA in presence of 20, 50, and 100 µg/mL (empty, dotted, and full bars, respectively). Values are means of three trials made in triplicate, Y-error bars indicate standard deviation.

Figure 2.  Antifungal activity of the compounds 5a-g and 6 expressed as percentage inhibition of growth on test organisms. The fungi were cultured on PDA in presence of 20, 50, and 100 µg/mL (empty, dotted, and full bars, respectively). Values are means of three trials made in triplicate, Y-error bars indicate standard deviation.

Figure 3.  Cultures of Sclerotinia minor control and treated with compound 5a (G8) at 100 µg/mL: in the control are evident black sclerotia, which are instead absent after treatment with 5a (plate on the right).

Figure 3.  Cultures of Sclerotinia minor control and treated with compound 5a (G8) at 100 µg/mL: in the control are evident black sclerotia, which are instead absent after treatment with 5a (plate on the right).

Figure 4.  Comparison between the antifungal activity on M. grisea of the compounds 5a5b and the reference compound, tricyclazole, treated at the same doses.

Figure 4.  Comparison between the antifungal activity on M. grisea of the compounds 5a–5b and the reference compound, tricyclazole, treated at the same doses.

Figure 5.  Cultures of M. grisea control and treated with compound 5b (G8-1) at 20, 50, and 100 µg/mL: the mycelia of the treated samples exhibited a very darker pigmentation than the control.

Figure 5.  Cultures of M. grisea control and treated with compound 5b (G8-1) at 20, 50, and 100 µg/mL: the mycelia of the treated samples exhibited a very darker pigmentation than the control.

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