potassium 2-oxocyclooctylsulfonate | 1094389-71-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: potassium 2-oxocyclooctylsulfonate
• 英文别名: Potassium;2-oxocyclooctane-1-sulfonate
• CAS: 1094389-71-5
• 化学式: C₈H₁₃O₄S*K
• 分子量: 244.353
• InChiKey: QVWTZAVBWYJZPA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.17
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  82.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  potassium 2-oxocyclooctylsulfonate 在 sodium tetrahydroborate 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 C₁₄H₁₈Cl₃NO₃S
  参考文献：
  名称：

  Synthesis and Fungicidal Activity of N-(2,4,5-trichlorophenyl)-2-Oxo-and 2-Hydroxycycloalkylsulfonamides

  摘要：

  以主要化合物螯磺酰胺（代号：CAUWL-2004-L-13）为基础，设计并合成了一系列 N-(2,4,5-三氯苯基)-2-氧代和 2-羟基环烷基磺酰胺（系列 II 和 III）。通过 1H NMR、IR 和元素分析确认了它们的结构。化合物 II 和 III 在体外和体内都显示出对灰霉病菌的卓越活性。菌丝生长和分生孢子萌发试验表明，化合物 IId 的 EC50 分别为 0.64 μg mL-1 和 0.34 μg mL-1。在黄瓜幼苗中对银环孢菌的体内控制方面，化合物 IIb 和 IId 比商用杀菌剂丙嘧菌酯和嘧菌酯表现出更好的控制效果。此外，与百菌清相比，这些新化合物的杀菌谱更广。环烷烃的大小对杀菌活性有明显的影响。所有具有六元环、七元环和八元环的化合物都表现出较高的杀菌活性。

  DOI：

  10.2174/1570180811310040009
• 作为产物：
  描述：

  环辛酮 在 sulfur trioxide dioxane complex 、 potassium hydroxide 作用下， 以 水 为溶剂， 以82%的产率得到potassium 2-oxocyclooctylsulfonate
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1021/jf102348x

文献信息

• Novel sulfonamides against Botrytis cinerea with no positive cross-resistance to commercial fungicides: Design, synthesis and SAR study
  作者：Nan Cai、Lu He、Kai Wang、Zhihui Feng、Zining Cui、Mingshan Ji、Zhiqiu Qi、Peiwen Qin、Xinghai Li

  DOI：10.1016/j.bmcl.2019.126859

  日期：2020.2

  Thirty-four novel compounds were synthesized using chesulfamide (N-(2-trifluoromethyl-4-chlorophenyl)-2-oxocyclohexyl sulfonamide), a high-profile fungicide, as the lead compound, and their structures were characterized by H-1 NMR, C-13 NMR, MS and elemental analysis. Additionally, the structure of (1S,2R)-2-((3-bromophenethyl)amino)-N-(4-chloro-2-trifluoromethylphenyl)cyclohexane-1-sulfonamide (IV-9) was confirmed by X-ray single crystal diffraction. The mycelium inhibition tests, spore germination inhibition tests, tomato pot tests and field trials were performed against strains of B. cinerea. Bioassay results showed that most of target compounds had good fungicidal activity against B. cinerea, in particular, IV-9 exhibited similar or superior effects to procymidone, boscalid and pyrisoxazole in all in vitro and in vivo tests. Moreover, there was no positive cross-resistance found between the compound IV-9 and eight commercial fungicides (azoxystrobin, boscalid, chlorothalonil, diethofencarb, fludioxonil, procymidone, pyrimethanil and pyrisoxazole) in the cross-resistance validation test performed by an innovative method.