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Synthesis and Fungicidal Activity of ( E )‐5‐[1‐(2‐Oxo‐1‐oxaspiro[4,5]dec/non‐3‐en‐3‐yl)ethylidene]‐2‐aminoimidazolin‐4‐one Derivatives
Author(s) -
Tang Bo,
Guan Aiying,
Zhao Yu,
Jiang Jiazhen,
Wang Mingan,
Zhou Ligang
Publication year - 2017
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201600794
Subject(s) - chemistry , phytophthora capsici , mycelium , fungicide , spore germination , bioassay , hypha , colletotrichum capsici , germination , stereochemistry , nuclear chemistry , horticulture , botany , food science , pepper , genetics , biology
The novel fungicidal agents, ( E )‐5‐[1‐(2‐oxo‐1‐oxaspiro[4,5]dec/non‐3‐en‐3‐yl)ethylidene]‐2‐aminoimidazolin‐ 4‐one derivatives, were designed and synthesized in moderate to excellent yields in four steps using α ‐hydroxyketone and diketene as raw materials and characterized by HR‐ESI‐MS , 1 H NMR and X‐ray diffraction. The preliminary bioassay showed that some of these compounds, such as 5e , 6a , 6e , and 7 h exhibit 87.8%, 91.3%, 89.9% and 87.8% inhibition rates against Sclerotinia scleotiorum , 3b , 3c , 4c and 7 h exhibit 96.4%, 92.5%, 90.3% and 76.9% inhibition rates against Phytophthora capsici at the concentration of 50 µg/ mL , respectively. These compounds exhibited significant fungicidal activities against S. scleotiorum and P. capsici with EC 50 values of 2.56–11.60 µg/ mL , and compounds 6e and 7 h exhibited weak inhibition against the spore germination of S. scleotiorum , while the spore germination of P. capsici was strongly inhibited by compound 7 h solution. Scanning electron microscopy ( SEM ) and transmission electron microscopy ( TEM ) observation indicated that compound 7 h had a significant impact on the structure and function of the hyphal cell wall of P. capsici mycelium.