Dehydrozingerone Inspired Discovery of Potential Broad-Spectrum Fungicidal Agents as Ergosterol Biosynthesis Inhibitors

A series of dehydrozingerone derivatives were synthesized, and their fungicidal activities and action mechanism against Colletotrichum musae were evaluated. The bioassay result showed that most compounds exhibited excellent fungicidal activity in vitro at 50 μg mL–1. Compounds 13, 16, 18, 19, and 27...

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Published inJournal of agricultural and food chemistry Vol. 67; no. 41; pp. 11354 - 11363
Main Authors Song, Xiangmin, Zhu, Xinyue, Li, Ting, Liang, Cai, Zhang, Meng, Shao, Yu, Tao, Jun, Sun, Ranfeng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.10.2019
Amer Chemical Soc
Subjects
Agriculture
Agriculture, Multidisciplinary
Chemistry
Chemistry, Applied
Food Science & Technology
Life Sciences & Biomedicine
Physical Sciences
Science & Technology
action mechanism
ergosterol biosynthesis inhibitors
dehydrozingerone
fungicidal activity
KETONES
MECHANISM
ANTIFUNGAL ACTIVITY
ESTERS
DERIVATIVES
TRIFLUOROMETHYLATION
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Summary:A series of dehydrozingerone derivatives were synthesized, and their fungicidal activities and action mechanism against Colletotrichum musae were evaluated. The bioassay result showed that most compounds exhibited excellent fungicidal activity in vitro at 50 μg mL–1. Compounds 13, 16, 18, 19, and 27 exhibited broad-spectrum fungicidal activity; especially, compounds 19 and 27 were found to have more potent fungicidal activity than azoxystrobin. The EC50 values of compounds 19 and 27 against Rhizoctonia solani were 0.943 and 0.161 μg mL–1 respectively. Moreover, compound 27 exhibited significant in vitro bactericidal activity against Xanthomonas oryzae pv. oryzae, with an EC50 value of 11.386 μg mL–1, and its curative effect (49.64%) and protection effect (51.74%) on rice bacterial blight disease was equivalent to that of zhongshengmycin (42.90%, 40.80% respectively). Compound 27 could also effectively control gray mold (87.10%, 200 μg mL–1) and rice sheath blight (100%, 200 μg mL–1; 82.89%, 100 μg mL–1) in vivo. Preliminary action mechanism study showed that compound 27 mainly acted on the cell membrane and significantly inhibited ergosterol biosynthesis in Colletotrichum musae.
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ISSN:0021-8561
1520-5118
DOI:10.1021/acs.jafc.9b04231