Synthesis and Fungicidal Activity of Novel 2,5-Disubstituted-1,3,4-oxadiazole Derivatives

Abstract

A novel series of 1,3,4-oxadiazole derivatives containing a 5-phenyl-2-furan moiety were synthesized from the intermediates diacylhydrazine 3 and acylhydrazone 5 via an efficient approach under microwave irradiation in good yields. Their structures were characterized by IR, (1)H NMR, and elemental analysis. The antifungal tests indicated that the title compounds showed in vivo fungicidal activity against Botrytis cinerea and Rhizoctonia solanii at 500 μg/mL obviously. Some tested compounds even had a superiority effect over the commercial fungicides 40% Pyrimethanil SC and 3% Validamycin AS. The activity between the title compound and their precursors diacylhydrazine 3 and acylhydrazone 5 was also compared and discussed.

Design, Synthesis and Bioactivity of N-Glycosyl-N'-(5-substituted phenyl-2-furoyl) Hydrazide Derivatives

“…The compounds with fluoride and nitro group on the ortho ( III-6 and III-9 ) or para- position ( III-7 and III-8 ) showed better activity than the others. It could be deduced that the skeleton of 5-phenyl-2-furoyl hydrazide (hydrazone) displayed important antitumor activity, which was in agreement with our former results [20–24,26,27]. …”

“…In our previous work, based on the hydrazide moiety, some diacylhydrazines ( B , Scheme 1) [20–24], semicarbazides ( C , Scheme 1) [25], and acylhydrazones ( D , Scheme 1) [26,27] derivatives containing 5-phenyl-2-furan were designed and synthesized. All the compounds showed diverse and significant bioactivities such as fungicidal, insecticidal, and antitumor activities.…”

Synthesis and Bioactivity of 5-Substituted-2-furoyl Diacylhydazide Derivatives with Aliphatic Chain

“…Cell constants at 113(2) K were determined by a least-square fit to the setting parameters of independent reflections measured on a Bruker SMART [12] 1000 CCD area-detector diffractometer (Bruker, Fallanden, Switzerland) with graphite-monochromated Mo K α radiation (λ = 0.071070 nm) and operating in the phi and scan modes. The structure was solved by the direct method with SHELXS-97 [24–27] and refined by the full-matrix least squares method on F2 data using SHELXL-97 [27,28].…”

“…Hydrazides are also key intermediates, especially in the preparation of pharmaceuticals and agrochemicals. Their synthesis has attracted significant attention due to their application as scaffolds in the construction of many nitrogen containing heterocycles, such as 1,2,4-triazoles [11], 1,3,4-oxadiazoles [12,13], 1,3,4-thiadiazoles [14], 1,2,4,5-tetrazines [15], etc .…”

Synthesis and biological evaluation of oxadiazole incorporated ellipticine derivatives as anticancer agents

“…Heterocyclic molecules such as 1,3,4-oxadiazoles constitute an important class of compounds in medicinal and pharmaceutical chemistry because of their remarkable biological and pharmacological properties. They have been displayed many biological activities, such as antibacterial [22], antifungal [23], insecticidal [24], antiviral [25], inflammatory [26], antitubercular [27], and antitumor [28,29] activity. Zibotentan (ZD4054) (2) was one of the most important drugs with 1,3,4-oxadiazole moiety exhibit the most potent anticancer properties [30].…”