Synthesis and fungicidal activity of novel 2-oxocycloalkylsulfonylureas.
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.
Li
Xing-Hai
XH
Key Laboratory of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, Beijing 100094, People's Republic of China.
Yang
Xin-Ling
XL
Ling
Yun
Y
Fan
Zhi-Jin
ZJ
Liang
Xiao-Mei
XM
Wang
Dao-Quan
DQ
Chen
Fu-Heng
FH
Li
Zheng-Ming
ZM
D005658:Fungi / Q000187:drug effects; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000494:pharmacology*; D005874:Gibberella / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D021281:Quantitative Structure-Activity Relationship; D013453:Sulfonylurea Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*
D005659:Fungicides, Industrial; D013453:Sulfonylurea Compounds