Synthesis, Crystal Structure and Biological Activity of Novel N‐substituted Diazabicyclo Derivatives

Abstract

A series of N-substituted diazabicyclo derivatives were designed and synthesized based on the active subunit combination and structure-activity relationship theory. The compounds were prepared by levulinic acid or ester with diamine, then acylation with phenoxy acetyl chloride or acetoxy acetyl chloride. All the structures were characterized by IR, 1 H NMR, 13 C NMR, MS, and elemental analysis. The single crystal of compound 4a was determined by X-ray crystallography. The preliminary bioassay showed that all products could protect soybean against injury caused by 2,4-D butylate to some extent.

Research Progress in the Design and Synthesis of Herbicide Safeners: A Review

“…As shown in Scheme 20, active substructure combinations were adopted, and a series of N-substituted diazabicyclo derivatives were reported by Ye and Fu's team. 78 Significantly, soybean was effectively protected from 2,4-D butyrate by the N-substituted diazabicyclo derivatives. The N-phenoxyacetyl group imparts higher activity to the compound, even better than the commercial safener BAS-145138.…”

Design, microwave-assisted synthesis, bioactivity and SAR of novel substituted 2-phenyl-2-cyclohexanedione enol ester derivatives

“…21 A class of new isoquinolinium-like compounds and novel chiral succinate dehydrogenase inhibitors was also designed by utilizing the active substructure combination theory, and they exhibited excellent and broad spectrum antifungal activity. 22,23 In connection with the facts mentioned above and our earlier work on the design and synthesis of N-containing heterocyclic safeners, [24][25][26] herein substituted 2-phenyl-2-cyclohexanedione enol ester derivatives were designed based on the SAR and active substructure combination (Scheme 1). Greenhouse experiments demonstrated that some of them exhibited promising safener activity for protecting crops from injury by clethodim.…”