Synthesis and evaluation of novel ferrocene‐substituted triadimenol analogues

Abstract

In search of potent 1H-1,2,4-triazole derivatives with improving antifungal activity, a class of novel ferrocene-triadimenol analogues was synthesized and their biological potential evaluated. Screening data revealed that these new derivatives did not have the antifungal activities of parent compounds, but showed unexpectedly promising plant growth regulatory activity.

Recent developments of metal-based compounds against fungal pathogens

“…Unfortunately, analogue 1 showed no growth inhibition on the studied fungi (C. albicans, C. glabrata, C. parapsilosis, and C. krusei). 46 Fang and co-workers prepared a wide variety of ferrocene derivatives containing 1,2,4-triazole, thiazole or both, such as ferrocenyl-substituted vinyl 1,2,4triazole derivatives (2Z, 2E), 47 ferrocene-triadimefon analogues (3), 48 ferrocene-triadimenol analogues (4), 49 1-ferrocenyl-3-aryl-2-(1H-1,2,4-triazol-1-yl)-prop-2-en-1-one derivatives (5, Fig. 5), 50 and N-substituted benzylidene-4-ferrocenyl-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazol-2-amine derivatives (6, Fig.…”

Ferrocene in agriculture: from agrochemicals and soil remediation to selective chemosensors

“…Moreover, quite often the same compounds revealed promising and somewhat unexpected plant growth regulatory activity. The synthesis is quite straightforward, starting from acetylferrocene, 1, [9][10][11][12][13][14][15] or ferrocenecarbaldehyde, 2, [16][17][18] and using classical organic reactions, as illustrated in Figures 3 and 4.…”

“…By reducing analogs of triadimefon, the corresponding ferrocenyl analogs of triadimenol, 8, were obtained [13]. They were tested as indicated above for the triadimefon analogs and generally did not exhibit any antifungal activity (Table 1, entry 5); however, all of them showed excellent plant growth regulatory ability, even larger than the keto precursors.…”

Synthesis, Crystal Structure and Thermal Properties of N-Acetyl-3-(2-furyl)-5-ferrocenyl-2-pyrazoline and N-Acetyl-3-(2-thienyl)-5-ferrocenyl-2-pyrazoline

“…Recent studies have shown that the combination of biological active N-heterocyclic compounds such as pyrazolines and pyrazoles with ferrocene moiety can result in favorable change of biological properties [29][30][31][32][33][34] which is rationalized as being due to their different membrane-permeation properties and anomalous metabolism [35][36][37][38]. As mentioned earlier, although 2-pyrazolines are amongst the most intensely studied compounds; N-acetylated ferrocenyl-2-pyrazoline derivatives are relatively less explored [29,32].…”