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新型 1,3,4-恶二唑-2-甲酰肼的分子多样性设计、合成及生物特征。

Design, Synthesis, and Biological Profiles of Novel 1,3,4-Oxadiazole-2-carbohydrazides with Molecular Diversity.

机构信息

State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China.

出版信息

J Agric Food Chem. 2022 Mar 9;70(9):2825-2838. doi: 10.1021/acs.jafc.1c07190. Epub 2022 Feb 24.

Abstract

To unceasingly expand the molecular diversity of 1,3,4-oxadiazole-2-carbohydrazides, herein, small fragments (including -CH-, -OCH-, and -SCH-) were incorporated into the target compounds to screen out the potential succinate dehydrogenase inhibitors (SDHIs). The bioassay results showed that the antifungal effects (expressed by EC) against , , , and could reach 1.29 (), 0.63 (), 1.50 (), and 2.09 () μg/mL, respectively, which were slightly lower than those of carbendazim (EC were 0.69, 0.13, 0.55, and 0.80 μg/mL, respectively). Especially, compound was extremely bioactive against () with an EC value of 0.45 μg/mL. This outcome was better than that of fluopyram (3.76 μg/mL) and was similar to prochloraz (0.47 μg/mL). trials against the corn scab (infected by ) showed that compound had control activity of 86.8% at 200 μg/mL, which was better than that of boscalid (79.6%). Further investigations found that compound could inhibit the enzymatic activity of SDH in the strain with an IC value of 3.67 μM, indicating that potential SDHIs might be developed. Additionally, the other biological activities of these molecules were screened simultaneously. The anti-oomycete activity toward afforded a minimal EC value of 3.22 μg/mL (); compound could strongly suppress the growth of bacterial strains pv. and pv. with EC values of 3.79 and 11.4 μg/mL, respectively; and compound displayed some insecticidal activity toward . Given their multipurpose features, these frameworks could be actively studied as potential pesticide leads.

摘要

为了不断扩展 1,3,4-恶二唑-2-甲脒类化合物的分子多样性,本文将小分子片段(包括-CH-、-OCH-和-SCH-)引入到目标化合物中,以筛选出潜在的琥珀酸脱氢酶抑制剂(SDHIs)。生物测定结果表明,化合物对、、、的抑菌效果(以 EC 表示)分别达到 1.29()、0.63()、1.50()和 2.09()μg/mL,略低于多菌灵(EC 分别为 0.69、0.13、0.55 和 0.80 μg/mL)。特别是,化合物对()的抑菌活性极高,EC 值为 0.45 μg/mL。这一结果优于氟吡菌酰胺(3.76 μg/mL),与咯菌腈(0.47 μg/mL)相当。田间试验表明,化合物在 200 μg/mL 时对玉米大斑病(由 引起)的防治效果为 86.8%,优于肟菌酯(79.6%)。进一步研究发现,化合物对 SDH 的酶活具有抑制作用,在 菌株中的 IC 值为 3.67 μM,表明可能开发出潜在的 SDHIs。此外,还同时筛选了这些分子的其他生物活性。对 化合物的抗卵菌活性给出了最小 EC 值 3.22 μg/mL();化合物对细菌菌株 pv. 和 pv. 的生长具有较强的抑制作用,EC 值分别为 3.79 和 11.4 μg/mL;化合物对 具有一定的杀虫活性。鉴于它们的多功能特性,这些结构框架可作为潜在的农药先导化合物进行积极研究。

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