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. 2015 Jun 24;20(7):11660-75.
doi: 10.3390/molecules200711660.

Antibacterial Activity and Mechanism of Action of Sulfone Derivatives Containing 1,3,4-Oxadiazole Moieties on Rice Bacterial Leaf Blight

Li Shi  1 , Pei Li  2 , Wenli Wang  3 , Manni Gao  4 , Zengxue Wu  5 , Xianpeng Song  6 , Deyu Hu  7
Affiliations

Antibacterial Activity and Mechanism of Action of Sulfone Derivatives Containing 1,3,4-Oxadiazole Moieties on Rice Bacterial Leaf Blight

Li Shi et al. Molecules. .

Abstract

In this study, sulfone derivatives containing 1,3,4-oxadiazole moieties indicated good antibacterial activities against rice bacterial leaf blight caused by the pathogen Xanthomonas oryzaepv. pv. oryzae (Xoo). In particular, 2-(methylsulfonyl)-5-(4-fluorobenzyl)-1,3,4-oxadiazole revealed the best antibacterial activity against Xoo, with a half-maximal effective concentration (EC50) of 9.89 μg/mL, which was better than those of the commercial agents of bismerthiazole (92.61 μg/mL) and thiodiazole copper (121.82 μg/mL). In vivo antibacterial activity tests under greenhouse conditions and field trials demonstrated that 2-(methylsulfonyl)-5-(4-fluorophenyl)-1,3,4-oxadiazole was effective in reducing rice bacterial leaf blight. Meanwhile, 2-(methylsulfonyl)-5-(4-fluorophenyl)-1,3,4-oxadiazole stimulate the increase in superoxide dismutase (SOD) and peroxidase (POD) activities in rice, causing marked enhancement of plant resistance against rice bacterial leaf blight. It could also improve the chlorophyll content and restrain the increase in the malondialdehyde (MDA) content in rice to considerably reduce the amount of damage caused by Xoo. Moreover, 2-(methylsulfonyl)-5-(4-fluorophenyl)-1,3,4-oxadiazole, at a concentration of 20 μg/mL, could inhibit the production of extracellular polysaccharide (EPS) with an inhibition ratio of 94.52%, and reduce the gene expression levels of gumB, gumG, gumM, and xanA, with inhibition ratios of 94.88%, 68.14%, 86.76%, and 79.21%, respectively.

Keywords: Xanthomonas oryzae pv. oryzae; action mechanism; antibacterial activity; extracellular polysaccharide; sulfone derivative.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Compounds previously reported against tobacco and tomato bacterial wilts.
Figure 2
Figure 2
The changes of SOD (a) and POD (b) activities (The data presented are the mean ± SD). T1: Xoo + Compound 2-(methyl sulfonyl)-5-(4-fluorophenyl)-1,3,4-oxadiazole; T2: Xoo + Bismerthiazol; T3: Xoo; T4: Untreated blank control.
Figure 3
Figure 3
The changes of chlorophyll content in rice (The data presented are the mean ± SD). T1: Xoo + Compound 2-(methylsulfonyl)-5-(4-fluorophenyl)-1,3,4-oxadiazole; T2: Xoo + Bismerthiazole; T3: Xoo; T4: Untreated blank control.
Figure 4
Figure 4
The changes of MDA content in rice (The data presented are the mean ± SD). T1: Xoo + Compound 2-(methyl sulfonyl)-5-(4-fluorophenyl)-1,3,4-oxadiazole; T2: Xoo + Bismerthiazol; T3: Xoo; T4: Untreated blank control.
Figure 5
Figure 5
Effect on the biofilm formation. A: Untreated blank control; B: Xoo + Compound 2-(methylsulfonyl)-5-(4-fluorophenyl)-1,3,4-oxadiazole.
Figure 6
Figure 6
Inhibition rate of EPS of Xoo (The data presented are the mean ± SD). T1: Xoo + Compound 2-(methylsulfonyl)-5-(4-fluorophenyl)-1,3,4-oxadiazole; T2: Untreated blank control.
Figure 7
Figure 7
Expression of EPS gene of Xoo (The data presented are the mean ± SD). T1: Untreated blank control; T2: gumB; T3: gumG; T4: gumM; T5: xanA.
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