1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfanyl-5-[[2,2,2-trichloro-1-(2-fluoroethoxy)ethyl]amino]pyrazole-3-carbonitrile | 1222566-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfanyl-5-[[2,2,2-trichloro-1-(2-fluoroethoxy)ethyl]amino]pyrazole-3-carbonitrile
• CAS: 1222566-13-3
• 化学式: C₁₆H₁₁Cl₅F₄N₄OS
• 分子量: 560.614
• InChiKey: JYKIDNVYSOLGNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfanyl-5-[[2,2,2-trichloro-1-(2-fluoroethoxy)ethyl]amino]pyrazole-3-carbonitrile 在 双氧水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 、
  参考文献：
  名称：

  Design, Synthesis and Insecticidal Activity of Novel Phenylpyrazoles Containing a 2,2,2-Trichloro-1-alkoxyethyl Moiety

  摘要：

  A series of novel phenylpyrazoles containing a 2,2,2-trichloro-1-alkoxyethyl moiety were designed and synthesized via the key intermediate 5-trichloroethyl-ideneimino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-alkylsulfenylpyrazole (5). The addition reaction of the imine 5 was closely related with the nature of the alcohol. The target compounds were confirmed by H-1 NMR and elemental analysis. The results of bioassays indicated that the target compounds possessed excellent activities against a broad spectrum of insects such as bean aphid (Aphis craccivora), mosquito (Culex pipiens pallens) and diamondback moth (Plutella xylostella). Especially, the foliar contact activity against bean aphid of compound 7h at 2.5 mg kg(-1) was 89%, the larvacidal activity against mosquito of compound 6c at 2.5 mu g kg(-1) was 100%, the activity against diamondback moth of compound 7a at 5 mg kg(-1) was 87%, and all of these activities were much higher than the contrast ethiprole. The results of insecticidal activities showed that the two pairs of enantiomers 7d-1 and 7d-2 gave activities without distinctive difference, and it was the similar situation for 7e-1 and 7e-2. Interestingly, the target compounds exhibited high selectivity between diamondback moth and oriental armyworm, both of which are of the order Lepidoptera. The 2,2,2-trichloro-1-alkoxyethyl moiety was essential for high insecticidal activities.

  DOI：

  10.1021/jf1001793
• 作为产物：
  描述：

  4,4'-二硫烷二基二{5-氨基-1-[2,6-二氯-4-(三氟甲基)苯基]-1H-吡唑-3-甲腈} 在 dipotassium hydrogenphosphate 、 sodium dithionite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfanyl-5-[[2,2,2-trichloro-1-(2-fluoroethoxy)ethyl]amino]pyrazole-3-carbonitrile
  参考文献：
  名称：

  Design, Synthesis and Insecticidal Activity of Novel Phenylpyrazoles Containing a 2,2,2-Trichloro-1-alkoxyethyl Moiety

  摘要：

  A series of novel phenylpyrazoles containing a 2,2,2-trichloro-1-alkoxyethyl moiety were designed and synthesized via the key intermediate 5-trichloroethyl-ideneimino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-alkylsulfenylpyrazole (5). The addition reaction of the imine 5 was closely related with the nature of the alcohol. The target compounds were confirmed by H-1 NMR and elemental analysis. The results of bioassays indicated that the target compounds possessed excellent activities against a broad spectrum of insects such as bean aphid (Aphis craccivora), mosquito (Culex pipiens pallens) and diamondback moth (Plutella xylostella). Especially, the foliar contact activity against bean aphid of compound 7h at 2.5 mg kg(-1) was 89%, the larvacidal activity against mosquito of compound 6c at 2.5 mu g kg(-1) was 100%, the activity against diamondback moth of compound 7a at 5 mg kg(-1) was 87%, and all of these activities were much higher than the contrast ethiprole. The results of insecticidal activities showed that the two pairs of enantiomers 7d-1 and 7d-2 gave activities without distinctive difference, and it was the similar situation for 7e-1 and 7e-2. Interestingly, the target compounds exhibited high selectivity between diamondback moth and oriental armyworm, both of which are of the order Lepidoptera. The 2,2,2-trichloro-1-alkoxyethyl moiety was essential for high insecticidal activities.

  DOI：

  10.1021/jf1001793

文献信息

• Design, Synthesis and Insecticidal Activity of Novel Phenylpyrazoles Containing a 2,2,2-Trichloro-1-alkoxyethyl Moiety
  作者：Qiqi Zhao、Yongqiang Li、Lixia Xiong、Qingmin Wang

  DOI：10.1021/jf1001793

  日期：2010.4.28

  A series of novel phenylpyrazoles containing a 2,2,2-trichloro-1-alkoxyethyl moiety were designed and synthesized via the key intermediate 5-trichloroethyl-ideneimino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-alkylsulfenylpyrazole (5). The addition reaction of the imine 5 was closely related with the nature of the alcohol. The target compounds were confirmed by H-1 NMR and elemental analysis. The results of bioassays indicated that the target compounds possessed excellent activities against a broad spectrum of insects such as bean aphid (Aphis craccivora), mosquito (Culex pipiens pallens) and diamondback moth (Plutella xylostella). Especially, the foliar contact activity against bean aphid of compound 7h at 2.5 mg kg(-1) was 89%, the larvacidal activity against mosquito of compound 6c at 2.5 mu g kg(-1) was 100%, the activity against diamondback moth of compound 7a at 5 mg kg(-1) was 87%, and all of these activities were much higher than the contrast ethiprole. The results of insecticidal activities showed that the two pairs of enantiomers 7d-1 and 7d-2 gave activities without distinctive difference, and it was the similar situation for 7e-1 and 7e-2. Interestingly, the target compounds exhibited high selectivity between diamondback moth and oriental armyworm, both of which are of the order Lepidoptera. The 2,2,2-trichloro-1-alkoxyethyl moiety was essential for high insecticidal activities.