Synthesis and Antifungal Activity of Novel Sulfone Derivatives Containing 1,3,4-Oxadiazole Moieties

Abstract

A series of new sulfone compounds containing 1,3,4-oxadiazole moieties were synthesized. The structures of these compounds were confirmed by spectroscopic data (IR, 1H- and 13C-NMR) and elemental analyses. Antifungal tests indicated that all the title compounds exhibited good antifungal activities against eight kinds of plant pathogenic fungi, and some showed superiority over the commercial fungicide hymexazol. Among them, compounds 5d, 5e, 5f, and 5i showed prominent activity against B. cinerea, with determined EC50 values of 5.21 μg/mL, 8.25 µg/mL, 8.03 µg/mL, and 21.00 µg/mL, respectively. The present work demonstrates that sulfone derivatives such as 5dcontaining a 1,3,4-oxadiazole moiety can be used as possible lead compounds for the development of potential agrochemicals.

Design, synthesis, insecticidal activity and 3D-QSR study for novel trifluoromethyl pyridine derivatives containing an 1,3,4-oxadiazole moiety

“…Substituted benzoyl hydrazine (C) was prepared by following the known procedure. 25 Substituted benzoic acid or para-uorophenyl-acetic acid (for preparation of compound E28) as starting materials, followed by esterication and hydrazinolysis to yield substituted 2-phenoxyacetohydrazide in excellent yields.…”

“…[10][11][12][13][14][15][16] Such as sulfoxaor, a representative commercial insecticide, and was industrialized by Dow Agroscience. 16 1,3,4-Oxadiazole derivative is a highly active pharmacophore and widely was used in pesticide molecules, 17 many active substance containing such a scaffold have been reported as insecticides, [18][19][20][21][22][23][24] fungicides, [25][26][27][28][29][30][31] and herbicides, 32-34 some of them were treated as a pesticide candidate for further industrialization. 25 Recently, Liu and co-workers reported the 1,3,4-oxadiazole derivative with an anthranilic diamide moiety possessed excellent insecticidal activity against P. xylostella, 20 as well as some insecticidal sarisan analogues with an 1,3,4-oxadiazole scaffold were developed by Guo et al 23,35 And in our recent work, a series of insecticidal 1,3,4-oxadiazole molecules bearing a 3-chloropyridin-2-yl-1H-pyrazole was proposed.…”

Synthesis and biological activity of arylsulfonamide derivatives containing 2-arylamino-4(3<i>H</i>)-quinazolinone

“…20,21) The fungi were provided by Kaili University, Guizhou, P. R. China. All the final compounds were dissolved in 1 mL of dimethylsulfoxide (DMSO).…”

Biological Activity of 5-(2,3,4-Pyridyl)-1,3,4-Oxadiazol-2- Thiones and Their Derivatives.

“…Researchers Weiming Xu [50] Patent of Chinese researchers [51] provides data on the compounds on the basis of 5-(4- These compounds are the basis of the fungicidal drug for prevention and treatment of diseases of bacterial speck in tomatoes, late blight and gray mold in cucumbers.…”