Synthesis, Fungicidal Activity, and Structure−Activity Relationship of 2-Oxo- and 2-Hydroxycycloalkylsulfonamides

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• 作者：Xing-Hai Li ; De-Cai Wu ; Zhi-Qiu Qi ; Xiu-Wei Li ; Zu-Min Gu ; Song-Hong Wei ; Yang Zhang ; Ying-Zi Wang ; Ming-Shan Ji
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2010
• 出版时间：November 10, 2010
• 年：2010
• 卷：58
• 期：21
• 页码：11384-11389
• 全文大小：756K
• 年卷期：v.58,no.21(November 10, 2010)
• ISSN：1520-5118

文摘

To explore new potential fungicides, a series of novel compounds, including 11 2-oxocycloalkylsulfonamide (3) and 21 2-hydroxycycloalkylsulfonamide (4) derivatives, were synthesized and their structures were confirmed by ¹H nuclear magnetic resonance (NMR), infrared (IR), and elemental analysis. The results of the bioassay showed that the compounds 3 and 4 possessed excellent fungicidal activity against Botrytis cinerea Pers. both in vitro and in vivo. The fungicidal activity of the compounds with 7- or 8-membered rings is better than those with 5-, 6-, or 12-membered rings. According to the results of the mycelium growth rate test, the EC₅₀ values of the compounds 3C, 4C, 3D, and 4D were 0.80, 0.85, 1.22, and 1.09 μg/mL, respectively, and similar to or better than commercial fungicide procymidone. The bioassay results of spore germination indicated that most of the compounds exhibited obvious inhibitory effects against B. cinerea and the inhibition rates of 2-oxocycloalkylsulfonamides were higher than 2-hydroxycycloalkylsulfonamides, among them. The EC₅₀ values of compounds 3A, 3B₁₇, 3E, and 4A were 4.21, 4.21 3.24, and 5.29 μg/mL, respectively. Those compounds containing 5- or 6-membered rings showed better activity than those containing 7-, 8-, or 12-membered rings. Furthermore, the results of the pot culture test showed that almost all of the compounds had effective control activity in vivo and 2-hydroxycycloalkylsulfonamides were obviously superior to 2-oxocycloalkylsulfonamides. The compounds 3E, 4C and 4D presented higher control efficacy than procymidone and pyrimethanil against gray mold disease on cucumber plants.

Keywords (keywords):

2-Hydroxycycloalkylsulfonamides; synthesis; Botrytis cinerea; fungicidal activity; structure−activity relationship