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
The novel fungicidal agents, (E)-5-[1-(2-oxo-l-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 a-hydroxyketone and diketene as raw materials and characterized by HR-ESI-MS, 1H NMR and X...
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Published in | 中国化学:英文版 Vol. 35; no. 7; pp. 1133 - 1140 |
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Main Author | |
Format | Journal Article |
Language | English |
Published |
2017
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Subjects | |
Online Access | Get full text |
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Summary: | The novel fungicidal agents, (E)-5-[1-(2-oxo-l-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 a-hydroxyketone and diketene as raw materials and characterized by HR-ESI-MS, 1H NMR and X-ray diffraction. The preliminary bioassay showed that some of these compounds, such as 5e, 6a, 6e, and 7h exhibit 87.8%, 91.3%, 89.9% and 87.8% inhibition rates against Sclerotinia scleotiorum, 3b, 3c, 4c and 7h 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 EC50 values of 2.56 --11.60 μg/mL, and compounds 6e and 7h exhibited weak inhibition against the spore germination of S. scleoti- orum, while the spore germination ofP. capsici was strongly inhibited by compound 7h solution. Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) observation indicated that compound 7h had a significant impact on the structure and function of the hyphal cell wall ofP. capsici mycelium. |
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Bibliography: | The novel fungicidal agents, (E)-5-[1-(2-oxo-l-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 a-hydroxyketone and diketene as raw materials and characterized by HR-ESI-MS, 1H NMR and X-ray diffraction. The preliminary bioassay showed that some of these compounds, such as 5e, 6a, 6e, and 7h exhibit 87.8%, 91.3%, 89.9% and 87.8% inhibition rates against Sclerotinia scleotiorum, 3b, 3c, 4c and 7h 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 EC50 values of 2.56 --11.60 μg/mL, and compounds 6e and 7h exhibited weak inhibition against the spore germination of S. scleoti- orum, while the spore germination ofP. capsici was strongly inhibited by compound 7h solution. Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) observation indicated that compound 7h had a significant impact on the structure and function of the hyphal cell wall ofP. capsici mycelium. (E)-5-[ 1-(2-oxo- 1-oxaspiro[4.5]dec/non-3-en-3-yl)ethylidene]-2-aminoimidazolin-4-one, synthesis,fungicidal activities 31-1547/O6 |
ISSN: | 1001-604X 1614-7065 |