2-(5-Ethyl-2-methylpyrazol-3-yl)-4-(4-pentoxyphenyl)-4,5-dihydro-1,3-oxazole | 1359764-55-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(5-Ethyl-2-methylpyrazol-3-yl)-4-(4-pentoxyphenyl)-4,5-dihydro-1,3-oxazole
• CAS: 1359764-55-8
• 化学式: C₂₀H₂₇N₃O₂
• 分子量: 341.453
• InChiKey: BVXSEXBAZVYFHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-乙基-2-甲基-2H-吡唑-3-甲酸 在 氯化亚砜 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 2-(5-Ethyl-2-methylpyrazol-3-yl)-4-(4-pentoxyphenyl)-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  Design, Synthesis, and Insecticidal Activity of Novel Pyrazole Derivatives Containing α-Hydroxymethyl-N-benzyl Carboxamide, α-Chloromethyl-N-benzyl Carboxamide, and 4,5-Dihydrooxazole Moieties

  摘要：

  On the basis of commercial insecticides tebufenpyrad and tolfenpyrad, two series of novel pyrazole-5-carboxamides containing alpha-hydroxymethyl-N-benzyl or alpha-chloromethyl-N-benzyl and pyrazoles containing 4,5-dihydrooxazole moieties were designed and synthesized via the key intermediate 2-amino-1-(4-substituted) phenyl ethanol. The structures of target compounds were confirmed by H-1 NMR and elemental analysis or high-resolution mass spectrum (HRMS), and their activities against cotton bollworm (Helicoverpa armigera), diamondback moth (Plutella xylostella), bean aphid (Aphis craccivora), mosquito (Culex pipiens pallens), and spider mite (Tetranychus cinnabarinus) were tested. The results of bioassays indicated that compounds containing alpha-diloromethyloN-benzyl and compounds containing 4,5-dihydrooxazole showed high insecticidal activity against cotton bollworm. Especially, stomach activities of compounds Ij, Il, and IIe were 60% at 5 mg kg(-1). Moreover, the target compounds exhibited high selectivity between cotton bollworm and diamondback moth, although both of them belong to the order Lepidoptera. Although the activities against diamondback moth were at a low level, some of the target compounds exhibited antifeedant activity. The compounds also had good activities against bean aphid, mosquito, and spider mite. The foliar contact activity of compounds Ic, Id, le, and IIf against bean aphid were 95, 95, 100, and 95%, respectively, at 200 mg kg(-1). The miticidal and ovicidal activities of compound IIi against spider mite were both 95% at 200 mg kg(-1). Furthermore, a trivial change at 4-position of pyrazole ring would lead to great changes in properties and activities, which can easily be deduced by comparing the activities of compounds in series I (4-chloro-pyrazole compounds) with corresponding compounds in series II (4-hydro-pyrazole compounds), especially from the miticidal and ovicidal activities of Ii and IIi against spider mite.

  DOI：

  10.1021/jf204778v

文献信息

• Design, Synthesis, and Insecticidal Activity of Novel Pyrazole Derivatives Containing α-Hydroxymethyl-<i>N</i>-benzyl Carboxamide, α-Chloromethyl-<i>N</i>-benzyl Carboxamide, and 4,5-Dihydrooxazole Moieties
  作者：Hongjian Song、Yuxiu Liu、Lixia Xiong、Yongqiang Li、Na Yang、Qingmin Wang

  DOI：10.1021/jf204778v

  日期：2012.2.15

  On the basis of commercial insecticides tebufenpyrad and tolfenpyrad, two series of novel pyrazole-5-carboxamides containing alpha-hydroxymethyl-N-benzyl or alpha-chloromethyl-N-benzyl and pyrazoles containing 4,5-dihydrooxazole moieties were designed and synthesized via the key intermediate 2-amino-1-(4-substituted) phenyl ethanol. The structures of target compounds were confirmed by H-1 NMR and elemental analysis or high-resolution mass spectrum (HRMS), and their activities against cotton bollworm (Helicoverpa armigera), diamondback moth (Plutella xylostella), bean aphid (Aphis craccivora), mosquito (Culex pipiens pallens), and spider mite (Tetranychus cinnabarinus) were tested. The results of bioassays indicated that compounds containing alpha-diloromethyloN-benzyl and compounds containing 4,5-dihydrooxazole showed high insecticidal activity against cotton bollworm. Especially, stomach activities of compounds Ij, Il, and IIe were 60% at 5 mg kg(-1). Moreover, the target compounds exhibited high selectivity between cotton bollworm and diamondback moth, although both of them belong to the order Lepidoptera. Although the activities against diamondback moth were at a low level, some of the target compounds exhibited antifeedant activity. The compounds also had good activities against bean aphid, mosquito, and spider mite. The foliar contact activity of compounds Ic, Id, le, and IIf against bean aphid were 95, 95, 100, and 95%, respectively, at 200 mg kg(-1). The miticidal and ovicidal activities of compound IIi against spider mite were both 95% at 200 mg kg(-1). Furthermore, a trivial change at 4-position of pyrazole ring would lead to great changes in properties and activities, which can easily be deduced by comparing the activities of compounds in series I (4-chloro-pyrazole compounds) with corresponding compounds in series II (4-hydro-pyrazole compounds), especially from the miticidal and ovicidal activities of Ii and IIi against spider mite.