5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylthio-1H-pyrazole-3-carbonitrile | 120068-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylthio-1H-pyrazole-3-carbonitrile
• 英文别名: 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethylsulfanylpyrazole；5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethylsulfenylpyrazole；ethiprole sulfide；5-amino-3-cyano-4-(ethylthio)-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole；5-Amino-3-cyano-1-(2,6-dichloro-4-trifluromethylphenyl)-4-ethylthiopyrazole；5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethylthiopyrazole；5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfanylpyrazole-3-carbonitrile
• CAS: 120068-56-6
• 化学式: C₁₃H₉Cl₂F₃N₄S
• 分子量: 381.208
• InChiKey: BCUFJUKQRNLOQF-UHFFFAOYSA-N

物化性质

• 熔点：
  156-158 °C
• 沸点：
  471.3±45.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  92.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylthio-1H-pyrazole-3-carbonitrile 反应 41.0h， 生成 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfanyl-5-[(2,2,2-trichloro-1-propoxyethyl)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
• 作为产物：
  描述：

  乙虫腈 在 三氟乙酸酐 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以64%的产率得到5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylthio-1H-pyrazole-3-carbonitrile
  参考文献：
  名称：

  苯并吡唑杀虫剂的光化学，新陈代谢和GABA的增效作用：乙腈与氟虫腈相比。

  摘要：

  乙丙啶与氟吡苯胺（主要的苯基吡唑杀虫剂）不同，仅在于乙基亚磺酰基取代基取代了三氟甲基亚磺酰基部分。这项研究比较了它们的光化学，新陈代谢，对γ-氨基丁酸（GABA）受体的作用和杀虫效力。在暴露于阳光下为薄膜时，乙丙胺发生氧化（主要），还原和去乙基亚磺酰化，但未发生脱亚磺酰化，而氟虫腈的主要光反应是脱亚磺酰化。在体外人类表达的CYP3A4和体内小鼠脑和肝脏中，乙丙胺比氟虫腈的代谢砜形成更快。硫化物，亚砜，砜，和[]（3）H] EBOB的GABA受体测定（人重组β3同聚物和家蝇头膜）中乙腈和氟虫腈系列中的二氢呋喃和去磺酰基衍生物，以及对有和没有P450抑制增效剂哌啶基的家蝇的局部毒性丁醇。总体而言，乙丙胺系列在功效上与氟虫腈系列非常相似。

  DOI：

  10.1021/jf030439l

文献信息

• Derivatives of N-phenylpyrazoles
  申请人：——

  公开号：US05232940A1

  公开（公告）日：1993-08-03

  N-Phenylpyrazole derivatives of the formula: ##STR1## wherein R.sup.1 represents cyano, nitro, halogen, acetyl or formyl; R.sup.2 represents R.sup.5 SO.sub.2, R.sup.5 SO or R.sup.5 S in which R.sup.5 is optionally halogen substituted alkyl, alkenyl or alkynyl; R.sup.3 represents a hydrogen atom or a group NR.sup.6 R.sup.7 wherein R.sup.6 and R.sup.7 each represent hydrogen, alkyl, alkenylalkyl, alkynylalkyl, formyl, optionally halogen substituted alkanoyl, optionally halogen substituted alkoxycarbonyl, or alkoxymethyleneamino, halogen, or R.sup.6 and R.sup.7 together form a cyclic imide and R.sup.4 represents a substituted phenyl group possess arthropodicidal, plant nematocidal, anthelmintic and anti-protozoal properties; their preparation, compositions containing them and their use are described.

  N-苯基吡唑衍生物的化学式为：##STR1## 其中R.sup.1代表氰基，硝基，卤素，乙酰基或甲酰基；R.sup.2代表R.sup.5 SO.sub.2，R.sup.5 SO或R.sup.5 S，其中R.sup.5可选择地被卤素取代的烷基，烯基或炔基；R.sup.3代表氢原子或基团NR.sup.6 R.sup.7，其中R.sup.6和R.sup.7各自代表氢，烷基，烯基烷基，炔基烷基，甲酰基，可选择地被卤素取代的烷酰基，可选择地被卤素取代的烷氧羰基，或烷氧亚甲基氨基，卤素，或R.sup.6和R.sup.7一起形成环状亚酰胺，R.sup.4代表取代苯基团，具有杀虫，植物线虫，驱虫和抗原虫药物性质；描述了它们的制备，含有它们的组合物以及它们的用途。
• Substituted 3-thiocarbamoylpyrazoles
  申请人：Bayer Aktiengesellschaft

  公开号：US06518296B1

  公开（公告）日：2003-02-11

  The invention relates to novel substituted 3-thiocarbamoylpyrazoles of general formula (I), wherein m, n, R1, R2, R3 and Ar have the meanings cited in the description. The invention further relates to methods for the production and use thereof as pesticides.

  这项发明涉及一种新型的通式（I）中的取代3-硫代氨基吡唑，其中m、n、R1、R2、R3和Ar的含义如描述中所述。该发明还涉及其作为杀虫剂的生产和使用方法。
• Pesticidal 1-arylpyrazoles
  申请人：Rhone-Poulenc, Inc.

  公开号：US06350771B1

  公开（公告）日：2002-02-26

  The invention relates to novel 1-arylpyrazole oxime derivatives, of general formula (I) or (I bis) These compounds are found to be generally safe systemic insecticides for control of arthropod, nematode, helminth or protozoan pests including compositions and derivatives thereof.

  这项发明涉及新颖的1-芳基吡唑肟衍生物，通式为(I)或(I bis)。这些化合物被发现通常是安全的全身杀虫剂，用于控制节肢动物、线虫、蠕虫或原生动物害虫，包括其组合物和衍生物。
• A convenient conversion of pyrazolyl disulfide to sulfides by sodium dithionite and synthesis of sulfoxides
  作者：Ri-Yuan Tang、Ping Zhong、Qiu-Lian Lin

  DOI：10.1016/j.jfluchem.2006.04.002

  日期：2006.7

  Indirectly introduce trifluoromethylthio-, alkylthio-, and trifluoromethylsulfinyl to pyrazole ring by a convenient reaction of a pyrazolyl disulfide with F3CBr and alkyl halides in the presence of sodium dithionite at room temperature. Followed by selective oxidation with H2O2 or trichloroisocyanuric acid (TCCA) to give trifluoromethylsulfenyl phenylpyrazole, alkylsulfenyl phenylpyazole, trifluoromethylsulfinyl

  在室温下，在连二亚硫酸钠存在下，通过吡唑基二硫键与F 3 CBr和烷基卤化物的便捷反应，将三氟甲硫基，烷硫基和三氟甲硫基间接引入吡唑环。然后用H 2 O 2或三氯异氰尿酸（TCCA）选择性氧化，分别得到三氟甲基亚磺酰基苯基吡唑，烷基亚磺酰基苯基吡唑，三氟甲基亚磺酰基苯基吡唑4a（高效杀虫剂，名为氟虫腈）和乙基亚磺酰基苯基吡唑4c衍生物。
• 一种氧化法制备乙虫腈的工艺
  申请人：浙江海正化工股份有限公司

  公开号：CN104370818B

  公开（公告）日：2017-04-05

  本发明公开了一种氧化法制备高纯度乙虫腈的工艺，将适量原料5‑氨基‑3‑氰基‑1‑（2,6‑二氯‑4‑三氟甲基苯基）‑4‑乙基亚硫酰基吡唑（I）在有机溶剂中，在脂肪酸、双氧水参与下发生氧化反应，氧化反应完成后，再加入还原剂同时控制体系温度，然后以NaOH溶液调整体系酸碱度，再在升温回流后冷却结晶抽滤得到粗品乙虫腈，粗品乙虫腈（Ⅱ）经提纯即可得到合格品；其中，有机溶剂选用氯仿、二氯甲烷、二氯乙烷中的至少一种。本发明生产工艺简单、效率高、副产物少，在产品产率以及产品纯度上都得到了较大的突破，并且原料毒性相对较低，对环境污染较小，生产可控性好。