Synthesis 2017; 49(20): 4663-4669
DOI: 10.1055/s-0036-1588463
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Zhao Yu
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China   Email: wangma@cau.edu.cn
,
Tang Bo
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China   Email: wangma@cau.edu.cn
,
Guan Aiying
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China   Email: wangma@cau.edu.cn
,
Wang Weiwei
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China   Email: wangma@cau.edu.cn
,
Zhang Zhenhua
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China   Email: wangma@cau.edu.cn
,
Wang Mingan*
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China   Email: wangma@cau.edu.cn
› Author Affiliations
This work was financially supported by the National Natural Science Foundation of China (No. 21172254) and the Ph.D. Program of the Ministry of Education, China (No. 20130008110003).
Further Information

Publication History

Received: 12 April 2017

Accepted after revision: 20 May 2017

Publication Date:
05 July 2017 (eFirst)

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.

 
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