Synthesis and Fungicidal Activity of (E)-5-[1-(4-Phenyl-2-oxo-1-oxaspiro[4.5]dec-3-en-3-yl)ethylidene]-2-aminoimidazolin-4-one Derivatives

Published as part of the Special Topic Modern Strategies for Heterocycles Synthesis

Abstract

(E)-5-[1-(4-Phenyl-2-oxo-1-oxaspiro[4.5]dec-3-en-3-yl)eth­yl­idene]-2-aminoimidazolin-4-one derivatives, as novel fungicidal agents, are designed and synthesized in moderate to excellent yields in four steps from (1-hydroxycyclohexyl)(phenyl)methanone and diketene as the starting materials. The products are characterized by ¹H NMR and HRMS (ESI) analysis. An in vivo bioassay shows that some of the products exhibit good to excellent inhibition against P. cubensis and C. lagenarium, whilst up to 94.7% inhibition against P. capsici and up to 78.1% inhibition against B. cinerea is demonstrated in the in vitro bioassay. EC₅₀ values of 3.40 and 5.86 μg/mL are demonstrated against P. capsici and B. cinerea.

Keywords

(E)-5-[1-(4-phenyl-2-oxo-1-oxaspiro[4.5]dec-3-en-3-yl)eth­ylidene]-2-aminoimidazolin-4-one - synthesis - fungicidal activity - structure–activity relationship

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