2.10.1 1-[1-Phenyl-1-(4-substituted phenyl)methylimidazoles

Title compounds form part of a large claim for agricultural microbicides.[2.301] For example, substance 2.46 inhibits Phaseolus vulgaris on kidney beans, Pythium aphan-idermatum, Fusarium oxysporum and Rhizoctonia solani.

2.10.2 Biphenylyl-phenylmethyl-1H-imidazoles o-Biphenylylimidazol-1-ylphenylmethane 2.47 has been claimed as a medical fungi-cide.[2.302]


Compound 2.48 which is not only related to bifonazole, but also to naftifine, shows high activity against Candida strains.[2.303]

The most successful drug in this series however is bifonazole 2.49A [60628-96-8].[2.304, 2.305,2.306]

The success of bifonazole prompted a series of claims and papers for better syn-thesis.[2.112, 2.307, 2.308, 2.309, 2.310, 2.311, 2.312, 2.313, 2.314]

A series of 56 azole antifungal agents related to bifonazole, as discussed in sections 2.10 and 2.11, has been investigated by comparative molecular field analysis (CoMFA) to yield two models of alignment with predictive value.[2.315]

Bifonazole shows high in vivo efficacy against a number of dermatophytoses and candidoses, and also against Gram-negative microorganisms such as Legio-ne//a.[2.316] In comparison with several other standard antimycotics, bifonazole has been demonstrated to be a very weak allergen in humans.[2.317]

Lombazole 249B [60628-98-0] displays maximum activity against Corynebacte-rium species, Staphylococcus albus and Pityrosporum species, and forms the active agent in the preparation Twent™ against acne vulgaris and acne juveni-lis.[2.318]

For the indications given above, formulation is very important for bifonazole and lombazole.[2.319, 2.320, 2.321, 2.322, 2.323, 2.324, 2.325, 2.326, 2.327, 2.328, 2.329, 2.330] Bifonazole is characterized by a rather low solubility in water compared to other standard azole antimycotics. On complexing with b-cyclodextrin, solubility increases about 160-fold. Though the resultant complex appears to have lost activity against the common test organisms, addition of b-cyclodextrin to the aqueous phase of a galenic preparation (especially one with carbapol 1%), increases the inhibition zone size 2-to3-fold for Candida albicans, A. niger, S. cerevisiae and T. cutaneum. It seems that addition of the dextrin may result in a better release of the drug from its preparations. [2.331]

In experimental Trichophyton mentagrophytes or Microsporum canis infections of guinea pigs, oral bifonazole acts in the stratum corneum and in hair sheaths resulting in complete clearance within seven days.[2.332]

2.10.3 Vinylogs of 1-diphenylmethyl-1H-azoles

Some vinylogs 2.50 of bifonazole have been described.[2.333]

Some vinylogs 2.50 of bifonazole have been described.[2.333]

The best example (Az = Im, n = 1, R, R', R" = Cl; R = Cl, R'" = CH3) displays activity against Candida albicans and C. paratropicalis.[2.333] Others inhibit Trichophyton mentagrophytes, Microsporum canis, and Aspergillus fumigatus.

2.10.4 1-(2,2-Diphenylethyl)-1-H-azoles

1-(2-Diphenylethyl)azoles 2.51A have been claimed as antimycotics and fungici-des.[2.334]

1-(2-Diphenylethyl)azoles 2.51A have been claimed as antimycotics and fungici-des.[2.334]

They inhibit C. albicans, and control phytopathogens such as Phytophthora infestans, Plasmopara viticola, Poria monticola, Ulocladium consortiale, Aureoba-sidium pullulans, Aspergillus niger and Bacterium subtilis.[2.335] From these, the fungicide brolaconazole 2.51B, [118528-04-4] and its nitrate, sulfate and tosylate salts have been studied in detail.[2.336]

Interesting activity against Piricularia oryzae on crops, fruit, vegetable and ornamental plants has been observed, and use for the protection of wood and varnishes has been proposed.

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