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Structure-Based Bioisosterism Design, Synthesis, Biological Activity and Toxicity of 1,2,4-Oxadiazole Substituted Benzamides Analogues Containing Pyrazole Rings.

ABSTRACT: In order to discover pesticidal lead compounds with high activity and low toxicity, a series of novel benzamides substituted with pyrazole-linked 1,2,4-oxadiazole were designed via bioisosterism. The chemical structures of the target compounds were confirmed via ¹H NMR, ¹³C NMR and HRMS analysis. The preliminary bioassay showed that most compounds exhibited good lethal activities against Mythimna separate, Helicoverpa armigera, Ostrinia nubilalis and Spodoptera frugiperda at 500 mg/L. Particularly in the case of Mythimna separate, compound 14q (70%) exhibited obvious insecticidal activity. In addition, compound 14h demonstrated good fungicidal activity against Pyricularia oryae with an inhibition rate of 77.8%, and compounds 14e, 14k, 14n and 14r also showed certain antifungal activities (55.6-66.7%). The zebrafish toxicity test showed that the LC₅₀ of compound 14h was 14.01 mg/L, which indicated that it may be used as a potential leading compound for further structural optimization.

SUBMITTER: Tu MT

PROVIDER: S-EPMC9330712 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Synthesis, biological activity and toxicity to zebrafish of benzamides substituted with pyrazole-linked 1,2,4-oxadiazole.

Project description:To find pesticidal lead compounds with high activity, a series of novel benzamides substituted with pyrazole-linked 1,2,4-oxadiazole was designed and synthesized by using the splicing principle of active substructures. The chemical structures of the target compounds were confirmed by 1H NMR, 13C NMR and HRMS. The preliminary bioassay showed that most compounds displayed good larvicidal activities against mosquito larvae at 10 mg L-1. In particular, compound 12g exhibited obvious activity; its lethal rate reached up to 100% (at 5 mg L-1) and 55% (at only 2 mg L-1). Furthermore, compound 12f (70.6%) and 12h (100%) showed good fungicidal activities against Pyricularia oryzae, with EC50 values of 8.28 and 5.49 μg mL-1, respectively, which were superior to that of the control drug bixafen (9.15 μg mL-1). Finally, the LC50 of compound 12h to zebrafish embryo was 0.39 mg L-1, so it was classified as a high-toxic compound. Thus, this compound may be used as a potential lead compound for further structural optimisation to develop new compounds with high activity and low toxicity.

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Benzamides Substituted with Quinoline-Linked 1,2,4-Oxadiazole: Synthesis, Biological Activity and Toxicity to Zebrafish Embryo.

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Novel Hydroxamic Acids Containing Aryl-Substituted 1,2,4- or 1,3,4-Oxadiazole Backbones and an Investigation of Their Antibiotic Potentiation Activity.

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