title: Synthesis and Antibacterial Evaluation of New Sulfone Derivatives Containing 2-Aroxymethyl-1,3,4-Oxadiazole/Thiadiazole Moiety.
abstract: Sulfones are one of the most important classes of agricultural fungicides. To discover new lead compounds with high antibacterial activity, a series of new sulfone derivatives were designed and synthesized by introducing the aroxymethyl moiety into the scaffold of 1,3,4-oxadiazole/thiadiazole sulfones. Antibacterial activities against three phytopathogens (Xanthomonas oryzae pv. oryzae,Ralstonia solanacearum,Xanthomonas axonopodis pv. citri.) were assayed in vitro. As compared to the control of commercial fungicides and some reported sulfone fungicides, seven compounds5I-1-5I-7exerted remarkably higher activities with EC50values ranging from 0.45-1.86 μg/mL againstX. oryzaeand 1.97-20.15 μg/mL againstR. solanacearum. Exhilaratingly,5I-1,5I-2and5I-4displayed significant in vivo activity againstX. oryzaewith protective effect of 90.4%, 77.7%, and 81.1% at 200 μg/mL, respectively, much higher than that exhibited by Bismerthiazol (25.6%) and Thiadiazole-copper (32.0%). And the differential phytotoxicity of active derivatives was preliminarily checked. The results demonstrated that derivative of 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole sulfone can serve as potential alternative bactericides for the management of plant bacterial diseases.
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, China. happytt365@foxmail.com.|Zunyi Agricultural Products Quality and Safety Inspection and Testing Center, Room 698, Shanghai Road, Huichuan District, Zunyi 563000, Guizhou, China. happytt365@foxmail.com.
authors.forename: Shihu
authors.initials: S
authors.lastname: Su
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, China. zhouxia_j@126.com.
authors.forename: Xia
authors.initials: X
authors.lastname: Zhou
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, China. lgp899017@163.com.
authors.forename: Guoping
authors.initials: G
authors.lastname: Liao
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, China. qpuying000@163.com.
authors.forename: Puying
authors.initials: P
authors.lastname: Qi
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, China. linhong_j@126.com.
authors.forename: Linhong
authors.initials: L
authors.lastname: Jin
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015195:Drug Design; D008826:Microbial Sensitivity Tests; D010069:Oxadiazoles / Q000737:chemistry*; D010935:Plant Diseases / Q000382:microbiology; D043368:Ralstonia solanacearum / Q000187:drug effects*; D013329:Structure-Activity Relationship; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013830:Thiadiazoles / Q000737:chemistry*; D014974:Xanthomonas / Q000187:drug effects*
chemical_list: D000900:Anti-Bacterial Agents; D010069:Oxadiazoles; D013450:Sulfones; D013830:Thiadiazoles; C583463:1,3,4-oxadiazole
keywords: 1,3,4-oxadiazole/thiadiazole sulfone; antibacterial activity; aryloxymethyl; structure-activity relationship; synthesis