Key Laboratory of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, Beijing, People's Republic of China 100193.
J Agric Food Chem. 2010 Mar 10;58(5):2659-63. doi: 10.1021/jf903665f.
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, (1)H NMR, and (13)C NMR. The conformation of compounds 4F was determined via the crystal structure of a representative compound (4F(6)). The bioassay showed that compounds 4F have much better fungicidal activity against five fungi ( Botrytis cinerea Pers., Sclerotinia sclerotiorum , Rhizoctonia solani Kuhn., 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. 4F(6) 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.
从 12-氧代-1,15-十五烷内酰胺和 12-氧代-1,15-十五烷内酯分别合成了两个含有大环内酯或大环内酯和噻二唑啉环的新型螺化合物系列，1-硫代-2-烷基亚氨基-3,4,9-三氮杂-10-氧螺[4.15]二十烷基-3-烯（4F）和 1-硫代-2-烷基亚氨基-3,4-二氮杂-9-氧螺[4.15]二十烷基-3-烯（4G）。它们的结构通过元素分析、（1）H NMR 和（13）C NMR 得到证实。通过代表化合物（4F（6））的晶体结构确定了化合物 4F 的构象。生物测定表明，化合物 4F 对五种真菌（灰葡萄孢菌、核盘菌、立枯丝核菌、芦笋炭疽菌和稻瘟病菌）的杀菌活性明显优于化合物 4G。这一事实表明，氢键供体的存在对大环化合物的杀菌活性非常重要。4F（6）对稻瘟病菌表现出优异的杀菌活性，优于商业杀菌剂异噻菌胺，而 4F（13）对稻瘟病菌表现出优异的杀菌活性和对芦笋炭疽菌的良好杀菌活性。
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