Synthesis, characterization, and biological evaluation of novel ferrocene-triadimefon analogues

Synthesis and biological activity research of novel ferrocenyl-containing thiazole imine derivatives

“…In addition to their fungicidal activity, they also possess a very high level of plant growth regulatory activity on a wide variety of crops [14]. Recently, we reported some ferrocene-containing triazole compounds with biological activities, such as ferrocene-triadimefon analogues [15]; 1-ferrocenyl-3-aryl-2-(1H-1,2,4-triazol-1-yl)-prop-2-en-1-one derivatives [16]; 1-phenyl-3-ferrocenyl-4-triazolyl-5-aryldihydropyrazole [17]; 3-aryl-1-ferrocenylpropenone [18]. All the compounds show some degree of fungicidal activities and plant growth regulatory activities.…”

Synthesis and evaluation of novel ferrocene‐substituted triadimenol analogues

“…Compared with their ketone precursors 3, these triadimenol analogues 4 showed higher plant growth regulatory activity. 24 The target compounds 4a-j obvious promoted cotyledon rhizogenesis of cucumber seed at a concentration of 10 mg/l. Except for compounds 4b, 4e and 4g, the rest ferrocene analogues had a higher plant growth regulatory activity than Triadimefon.…”

“…To our disappointment, however, all the tested compounds were inactive against all selected mycelium as the same as their ketone precursors. 24 It is well known that the antifungal activities of the triazole derivatives are related to their interference with steroid biosynthesis and fungal cell-wall formation mediated by ferrous cytochrome-P450 enzymes. 14 It was hypothesized that binding of the triazole to ferrous of cytochrome-P450 enzymes was replaced by binding of the triazole to the ferrous atom of the ferrocene group; as a result, the antifungal activities of the title compounds 4a-j was retarded.…”

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.…”

“…Ferrocenyl analogs of triadimefon, 7, [12] were tested for antifungal activities against mildew and rusts on intravital wheat plants (Isariopsis clavispora, Bremia lactucae, C. fulvum, Erysiphe graminis, and Alternaria mali), but, disappointingly, all the tested compounds showed lower antifungal activity (see examples in Table 1, entry 4) against all fungi than parent triadimefon (92.8% and 96,6%, respectively). Instead, plant regulatory activity, assayed using cucumber cotyledon rhizogenesis method, resulted excellent.…”