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Molecules 2017, 22(1), 64; doi:10.3390/molecules22010064

Synthesis and Antibacterial Evaluation of New Sulfone Derivatives Containing 2-Aroxymethyl-1,3,4-Oxadiazole/Thiadiazole Moiety

1
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
2
Zunyi Agricultural Products Quality and Safety Inspection and Testing Center, Room 698, Shanghai Road, Huichuan District, Zunyi 563000, Guizhou, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Panayiotis A. Koutentis
Received: 21 November 2016 / Revised: 22 December 2016 / Accepted: 27 December 2016 / Published: 31 December 2016
(This article belongs to the Special Issue Sulfur-Nitrogen Heteroaromatics)
View Full-Text   |   Download PDF [2820 KB, uploaded 31 December 2016]   |  

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 compounds 5I-15I-7 exerted remarkably higher activities with EC50 values ranging from 0.45–1.86 μg/mL against X. oryzae and 1.97–20.15 μg/mL against R. solanacearum. Exhilaratingly, 5I-1, 5I-2 and 5I-4 displayed significant in vivo activity against X. oryzae with 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. View Full-Text
Keywords: synthesis; 1,3,4-oxadiazole/thiadiazole sulfone; aryloxymethyl; antibacterial activity; structure-activity relationship synthesis; 1,3,4-oxadiazole/thiadiazole sulfone; aryloxymethyl; antibacterial activity; structure-activity relationship
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Su, S.; Zhou, X.; Liao, G.; Qi, P.; Jin, L. Synthesis and Antibacterial Evaluation of New Sulfone Derivatives Containing 2-Aroxymethyl-1,3,4-Oxadiazole/Thiadiazole Moiety. Molecules 2017, 22, 64.

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