Li Xing-Hai, Yang Xin-Ling, Ling Yun, Fan Zhi-Jin, Liang Xiao-Mei, Wang Dao-Quan, Chen Fu-Heng, Li Zheng-Ming
Key Laboratory of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, Beijing 100094, People's Republic of China.
J Agric Food Chem. 2005 Mar 23;53(6):2202-6. doi: 10.1021/jf0403944.
A series of 2-oxocycloalkylsulfonylureas (2) have been synthesized in a six-step, three-pot reaction sequence from readily available cyclododecanone, cycloheptanone, and cyclohexanone. Their structures were confirmed by IR, 1H NMR, and elemental analysis. The bioassay indicated that some of them possess certain fungicidal activity against Gibberella zeae Petch. In general, compounds containing a 12-membered ring (2A) are more active than those containing a 6- or 7-membered ring (2B, 2C). In the series 2A, the compounds in which R is a disubstituted phenyl or pyrimidyl showed better activity than those in which R is a monosubstituted phenyl or pyrimidyl, and aryl-substituted compounds have somewhat higher activity than those substituted by pyrimidyl. The further bioassay showed that the representative of 2A, 2A15, has good fungicidal activities against not only G. zeae Petch but also Botrytis cinerea Pers, Colletotrichum orbiculare Arx, Pythium aphanidermatum Fitzp, Fusarium oxysporum Schl. f. sp. Vasinfectum, etc.
以易得的环十二酮、环庚酮和环己酮为原料，通过六步三釜反应序列合成了一系列2-氧代环烷基磺酰脲类化合物（2）。通过红外光谱、核磁共振氢谱和元素分析确定了它们的结构。生物活性测定表明，其中一些化合物对小麦赤霉病菌（Gibberella zeae Petch）具有一定的杀菌活性。一般来说，含有12元环的化合物（2A）比含有6元或7元环的化合物（2B、2C）活性更高。在2A系列中，R为二取代苯基或嘧啶基的化合物比R为单取代苯基或嘧啶基的化合物活性更好，且芳基取代的化合物比嘧啶基取代的化合物活性略高。进一步的生物活性测定表明，2A系列的代表化合物2A15不仅对小麦赤霉病菌具有良好的杀菌活性，而且对灰葡萄孢（Botrytis cinerea Pers）、瓜炭疽菌（Colletotrichum orbiculare Arx）、瓜果腐霉（Pythium aphanidermatum Fitzp）、尖孢镰刀菌（Fusarium oxysporum Schl. f. sp. Vasinfectum）等也具有良好的杀菌活性。
