Synthesis, Fungicidal Activity, and Structure−Activity Relationship of Spiro-Compounds Containing Macrolactam (Macrolactone) and Thiadiazoline Rings

Two series of novel spiro-compounds containing macrolactam or macrolactone and thiadiazoline rings, 1-thia-2-alkylimino-3,4,9-triaza-10-oxospiro[4.15]eicosyl-3-ene (4F) and 1-thia-2-alkylimino-3,4-diaza-9-oxa-10-oxospiro[4.15]eicosyl-3-ene (4G), were synthesized from 12-oxo-1,15-pentadecanlactam and...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2010-03, Vol.58 (5), p.2659-2663
Main Authors: Li, Jian-Jun, Liang, Xiao-Mei, Jin, Shu-Hui, Zhang, Jian-Jun, Yuan, Hui-Zhu, Qi, Shu-Hua, Chen, Fu-Heng, Wang, Dao-Quan
Format: Article
Language:English
Subjects:
Biological and medical sciences
Food industries
Fundamental and applied biological sciences. Psychology
Fungi - drug effects
Fungicides, Industrial - chemical synthesis
Fungicides, Industrial - chemistry
Fungicides, Industrial - pharmacology
Hydrogen Bonding
Lactams - chemical synthesis
Lactams - chemistry
Lactams - pharmacology
Magnetic Resonance Spectroscopy
Molecular Structure
Structure-Activity Relationship
Thiadiazoles - chemical synthesis
Thiadiazoles - chemistry
Thiadiazoles - pharmacology
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Summary:Two series of novel spiro-compounds containing macrolactam or macrolactone and thiadiazoline rings, 1-thia-2-alkylimino-3,4,9-triaza-10-oxospiro[4.15]eicosyl-3-ene (4F) and 1-thia-2-alkylimino-3,4-diaza-9-oxa-10-oxospiro[4.15]eicosyl-3-ene (4G), were synthesized from 12-oxo-1,15-pentadecanlactam and 12-oxo-1,15-pentadecanlactone, respectively. Their structures were confirmed by elemental analysis, 1H NMR, and 13C NMR. The conformation of compounds 4F was determined via the crystal structure of a representative compound (4F6 ). The bioassay showed that compounds 4F have much better fungicidal activity against five fungi (Botrytis cinerea Pers., Sclerotinia sclerotiorum, Rhizoctonia solani Kühn., Phomopsis asparagi Sacc., and Pyricularia oryzae Cav.) than compounds 4G. The fact above showed that the presence of a hydrogen-bonding donor for the fungicidal activity of macrocyclic compounds is very important. 4F6 showed excellent fungicidal activity against P. oryzae, which is much better than the commercial fungicide isoprothiolane, and 4F13 showed excellent fungicidal activity against P. oryzae and good fungicidal activity against P. asparagi.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf903665f