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首页> 外文期刊>Journal of Agricultural and Food Chemistry >Synthesis, Fungicidal Activity, and Structure-Activity Relationship of Spiro-Compounds Containing Macrolactam (Macrolactone) and Thiadiazoline Rings
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Synthesis, Fungicidal Activity, and Structure-Activity Relationship of Spiro-Compounds Containing Macrolactam (Macrolactone) and Thiadiazoline Rings

机译：含大环内酰胺（大环内酯）和噻二唑环的螺环化合物的合成，杀真菌活性和结构-活性关系

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摘要

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-pentade-canlactam and 12-oxo-1,15-pentadecanlactone, respectively. Their structures were confirmed by elemental analysis, ~1H NMR, and ~(13)C 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 (Bolrytis cinerea Pers., Sclerotlnia sclerotiorum, Rhlzoctonia solani Kiihn., Phomopsls 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 4F_(13) showed excellent fungicidal activity against P. oryzae and good fungicidal activity against P. asparagi.
机译：包含大环内酰胺或大环内酯和噻二唑环，1-噻二-2-烷基亚氨基-3,4,9-三氮杂-10-氧螺螺[4.15]二十烷基-3-烯（4F）和1-硫杂-环的两个新的螺化合物由12-氧代-1,15-戊烯-内酰胺和12-氧代-1合成2-烷基亚氨基-3,4-二氮杂-9-氧杂-10-氧杂螺[4.15]二十烷基-3-烯（4G） 15-pentadecanlactone，分别。通过元素分析，〜1H NMR和〜（13）C NMR确认了它们的结构。化合物4F的构型是通过代表性化合物（4F6）的晶体结构确定的。生物测定表明，化合物4F对5种真菌（Bolrytis cinerea Pers。，Sclerotlnia sclerotiorum，Rhlzoctonia solani Kiihn。，Phomopsls asparagi Sacc。和Pyricularia oryzae Cav。）的五种真菌具有更好的杀真菌活性。上述事实表明，对于大环化合物的杀真菌活性，氢键供体的存在是非常重要的。 4F6对稻瘟病菌显示出优异的杀真菌活性，远优于商品杀真菌剂异丙硫醇，而4F_（13）对稻瘟病菌显示出优异的杀真菌活性和对天门冬霉的良好杀真菌活性。

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