The Efficacy and Underlying Mechanism of Sulfone Derivatives Containing 1,3,4-oxadiazole on Citrus Canker

Abstract

Abstract:The objectives of the current study were to isolate and identify the pathogen responsible for citrus canker and investigate the efficacy of sulfone derivatives containing 1,3,4-oxadiazole moiety on controlling citrus canker caused by Xanthomonas citri subsp. citri (Xcc) under in vitro and field conditions. In an in vitro study, we tested eight sulfone derivatives against Xcc and the results demonstrated that compound 3 exhibited the best antibacterial activity against Xcc, with a half-maximal effective concentration (EC50) value of 1.23 μg/mL, which was even better than those of commercial bactericides Kocide 3000 (58.21 μg/mL) and Thiodiazole copper (77.04 μg/mL), respectively. Meanwhile, under field experiments, compound 3 treatments demonstrated the highest ability to reduce the disease of citrus canker in leaves and fruits in two different places relative to an untreated control as well as the commercial bactericides Kocide 3000 and Thiodiazole copper. Meanwhile, compound 3 could stimulate the increase in peroxidase (POD), polyphenol oxidase (PPO), and phenylalanine ammonia lyase (PAL) activities in the navel orange leaves, causing marked enhancement of plant resistance against citrus canker. Moreover, compound 3 could damage the cell membranes, destruct the biofilm formation, inhibit the production of extracellular OPEN ACCESSMolecules 2015, 20 14104 polysaccharide (EPS), and affect the cell membrane permeability to restrain the growth of the bacteria.

Xanthomonas citri subsp. citri: host interaction and control strategies

“…On the other hand, sulfone derivatives containing 1,3,4oxadiazole were tested in vitro and in field conditions to control X. citri growth (Li et al 2015;Wang et al 2018). After exposing navel oranges to three rounds of spray with 1,3,4oxadiazole, a 60-64% reduction in citrus canker was observed, compared to a 50-56% reduction obtained with copper-based compounds (Li et al 2015).…”

“…On the other hand, sulfone derivatives containing 1,3,4oxadiazole were tested in vitro and in field conditions to control X. citri growth (Li et al 2015;Wang et al 2018). After exposing navel oranges to three rounds of spray with 1,3,4oxadiazole, a 60-64% reduction in citrus canker was observed, compared to a 50-56% reduction obtained with copper-based compounds (Li et al 2015). In addition, when 1,2,4-triazole was combined with quinazolones, another class of antimicrobial molecules, a series of derivatives inhibited X. citri growth more effectively than the tested controls bismerthiazol and thiadiazol-copper (Fan et al 2018;Patel et al 2018).…”

Recent advances on the pesticidal activity evaluations of sulfone derivatives: A 2010 to 2020 decade inmini‐review

“…A series of 2,5‐disubstituted‐1,3,4‐oxadiazole/thiadiazole sulfone derivatives were synthesized by Li et al 48,49 Antibacterial bioassay results indicated that compound 23 (Figure 13) demonstrated the best in vitro antibacterial bioactivities against Xoo , Xoc , and Xac , with the EC 50 values of 1.07, 7.14, and 1.23 μg/mL, respectively, which were better than those of kocide 3000, bismerthiazol, and thiodiazole copper. Meanwhile, in vivo antibacterial activity tests at greenhouse conditions demonstrated that the controlling effects of compound 23 against rice bacterial leaf blight were better than those of bismerthiazol and thiodiazole copper.…”

Target Discovery in Ralstonia solanacearum through an Activity-Based Protein Profiling Technique Based on Bioactive Oxadiazole Sulfones

“…An efficient way that promotes the agrochemical discovery processes is to expand the amount and breadth of targets. Currently, a chemical proteomic technique termed “activity-based protein profiling” (ABPP) was widely exploited to unravel the protein targets and consequently stimulated and promoted the effective discovery of novel drugs both in the medical and agricultural fields. − Oxadiazole sulfone reagents represent a class of novel structures and exhibit broad-spectrum biological activities, such as antibacterial, − antifungal, − and antiviral activities . Among these structures, the candidate jiahuangxianjunzuo ( JHXJZ ) and its analogues indicate potent antibacterial activity against those uncontrollable diseases, including tobacco bacterial wilt. ,,, Our previous study identified that dihydrolipoamide S -succinyltransferase (DLST) is a major target of JHXJZ in Xanthomonas, such as Xanthomonas oryzae pv.…”