Synthesis, Fungicidal Activity, and Structure-Activity Relationship of 2-Oxo- and 2-Hydroxycycloalkylsulfonamides
Synthesis, Fungicidal Activity, and Structure-Activity Relationship of 2-Oxo- and 2-Hydroxycycloalkylsulfonamides
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DOI：
10.1021/jf102348x
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发表时间：
2010-11-10
影响因子：
6.1
通讯作者：
Ji, Ming-Shan
中科院分区：
文献类型：
--
作者：
Li, Xing-Hai;Wu, De-Cai;Ji, Ming-Shan
为开发新型杀菌剂，合成了11个2-氧代环烷基磺酰胺（3）和21个2-羟基环烷基磺酰胺（4）衍生物，其结构经H-1核磁共振（NMR）、红外光谱（IR）和元素分析确证。生物活性测定结果表明，化合物3和4对番茄灰霉病菌具有较好的体内外杀菌活性。含7元环或8元环的化合物的杀菌活性优于含5元环、6元环或12元环的化合物。根据菌丝生长速率测试结果，化合物3C、4C、3D和40的EC 50值分别为0.80、0.85、1.22和1.09 μ g/mL，与商业杀菌剂腐霉利相似或优于腐霉利。孢子萌发生物测定结果表明，大部分化合物对B具有明显的抑制作用。其中2-氧代环烷基磺酰胺类的抑制率高于2-羟基环烷基磺酰胺类。化合物3A、3B（17）、3E和4A的EC 50值分别为4.21、4.21、3.24和5.29 μ g/mL。含5-或6-元环的化合物比含7-、8-或12-元环的化合物显示出更好的活性。盆栽试验结果表明，几乎所有化合物均具有较好的防治活性，其中2-羟基环烷基磺酰胺类化合物的防治效果明显上级2-氧代环烷基磺酰胺类化合物。化合物3E、4C和4D对黄瓜灰霉病的防治效果优于腐霉利和嘧霉胺。
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 H-1 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 40 were 0.80, 0.85, 1.22, and 1.09 mu g/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, 3B(17), 3E, and 4A were 4.21, 4.21 3.24, and 5.29 mu g/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.