Li Xing-Hai, Wu De-Cai, Qi Zhi-Qiu, Li Xiu-Wei, Gu Zu-Min, Wei Song-Hong, Zhang Yang, Wang Ying-Zi, Ji Ming-Shan
Department of Pesticide Science, Plant Protection College, Shenyang Agricultural University, Shenyang 110161, Liaoning, People's Republic of China.
J Agric Food Chem. 2010 Nov 10;58(21):11384-9. doi: 10.1021/jf102348x. Epub 2010 Oct 7.
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 (1)H 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.
为探索新型潜在杀菌剂，合成了一系列新型化合物，包括11种2-氧代环烷基磺酰胺（3）和21种2-羟基环烷基磺酰胺（4）衍生物，并通过氢核磁共振（1H NMR）、红外光谱（IR）和元素分析对其结构进行了确证。生物测定结果表明，化合物3和4在体外和体内均对灰葡萄孢具有优异的杀菌活性。具有7元或8元环的化合物的杀菌活性优于具有5元、6元或12元环的化合物。根据菌丝生长速率试验结果，化合物3C、4C、3D和4D的EC50值分别为0.80、0.85、1.22和1.09μg/mL，与市售杀菌剂腐霉利相当或更好。孢子萌发生物测定结果表明，大多数化合物对灰葡萄孢表现出明显的抑制作用，其中2-氧代环烷基磺酰胺的抑制率高于2-羟基环烷基磺酰胺。化合物3A、3B17、3E和4A的EC50值分别为4.21、4.21、3.24和5.29μg/mL。那些含有5元或6元环的化合物比含有7元、8元或12元环的化合物表现出更好的活性。此外，盆栽试验结果表明，几乎所有化合物在体内均具有有效的防治活性，且2-羟基环烷基磺酰胺明显优于2-氧代环烷基磺酰胺。化合物3E、4C和4D对黄瓜植株灰霉病的防治效果高于腐霉利和嘧霉胺。
