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

J Agric Food Chem

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.

Published: March 2022

AI Article Synopsis

  • The study focuses on enhancing the diversity of 1,3,4-oxadiazole-2-carbohydrazides by adding small chemical fragments to identify new succinate dehydrogenase inhibitors (SDHIs).
  • Bioassay results show that these new compounds have antifungal effects, with some being more effective than traditional pesticides like carbendazim, particularly one compound that had exceptionally strong activity against a specific fungus.
  • Besides antifungal properties, the compounds also exhibited anti-oomycete and antibacterial activity, suggesting they have broad potential as new pesticide candidates.

Article 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.

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Source
http://dx.doi.org/10.1021/acs.jafc.1c07190DOI Listing

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