5-amino-3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-4-sulfonic acid | 209248-72-6

• 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-3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-4-sulfonic acid
• 英文别名: 5-Amino-3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-4-sulfonic acid；5-amino-3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole-4-sulfonic acid
• CAS: 209248-72-6
• 化学式: C₁₁H₅Cl₂F₃N₄O₃S
• 分子量: 401.153
• InChiKey: ABOHYNBXDJHVHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  氟虫腈 在 水 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 氟甲腈 、 5-amino-3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-4-sulfonic acid
  参考文献：
  名称：

  Kinetics and Mechanisms of Abiotic Degradation of Fipronil (Hydrolysis and Photolysis)

  摘要：

  The abiotic degradation of fipronil (compound I), a phenylpyrazole insecticide, was studied in aqueous solution and on the surface of two soils from Niger (Saguia and Banizoumbou) and one Mediterranean soil(Montpellier). The rate of hydrolysis of fipronil in solution was measured at different values of pH and temperature. The pH was an influencing factor: hydrolysis kinetics were pseudo-first-order, the half-life being 770 h at pH 9.0, 114 h at pH 10.0, 11 h at pH 11.0, and 2.4 h at pH 12.0. Fipronil was stable under acid (pH 5.5) and neutral conditions. The Arrhenius relation was verified over the temperature range 22-45 degrees C: the activation energy was 62 kJ mol(-1) and the calculated entropy change -32 J mol(-1). Compound II [5-amino-3-carbamoyl-1-(2,6-dichloro-4-(trifluoromethyl)-phenyl)-4-[(trifluoromethyl)sulfinyl]pyrazole] was the only hydrolysis product detected. The hydrolysis reaction mechanism involves nucleophilic addition of OH- to the polar nitrile bond, producing a hydroxyimine which then undergoes tautomerization into an amide. Fipronil in acidic (pH 5.5) aqueous solution exposed to light from a xenon lamp degraded with first-order kinetics (K-obs = 1.7 h(-1)) with concomitant appearance of 5-amino-3-cyano-1-(2, 6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethyl)pyrazole (compound III) and 5-amino-3-cyano-1-(2,6-dichlor0-4-(trifluoromethyl)-phenyl)pyrazole-4-sulfonic acid (compound IV). The photolyte formation rate constants were 0.II h(-1) (III) and 0.05 h(-1) (IV). The observed degradation process corresponded to a desulfinylation and an oxidation. The reaction mechanisms were not elucidated. The irradiation (xenon lamp) of fipronil adsorbed on three natural soils when dry led to the formation of 4-(trifluoromethyl)pyrazole (III). The K-obs values were 0.0047 h(-1) (Saguia), 0.0039 h(-1) (Banizoumbou), and 0.0032 h(-1) (Montpellier). The degree of photodegradation was inversely proportional to fipronil adsorption: the Freundlich adsorption coefficients were, respectively, 4.3 (Saguia), 7.3 (Banizoumbou), and 45.5 (Montpellier).

  DOI：

  10.1021/jf970874d

文献信息

• COMPOSITIONS AND USES THEREOF FOR CONTROLLING ECTOPARASITES IN NON-HUMAN MAMMALS
  申请人：Ceva Santé Animale

  公开号：EP3120846A1

  公开（公告）日：2017-01-25

  The invention relates to novel veterinary compositions comprising an effective amount of a neonicotinoid compound and an effective amount of a N-arylpyrazole compound. The invention also relates to the use of such compositions for controlling ectoparasites in a non-human mammal.

  本发明涉及新型兽用组合物，该组合物包含有效量的新烟碱化合物和有效量的 N-芳基吡唑化合物。本发明还涉及使用此类组合物控制非人类哺乳动物的体外寄生虫。
• METHODS FOR CONTROLLING ECTOPARASITES IN NON-HUMAN MAMMALS
  申请人：Ceva Santé Animale

  公开号：EP3259990A1

  公开（公告）日：2017-12-27

  The present invention relates to novel methods of treatment in the field of veterinary medicine, particularly methods for controlling ectoparasites in non-human mammals.

  本发明涉及兽医领域的新型治疗方法，特别是控制非人类哺乳动物体外寄生虫的方法。
• Compositions and uses thereof for controlling ectoparasites in non-human mammals
  申请人：Ceva Santé Animale

  公开号：US11134685B2

  公开（公告）日：2021-10-05

  The invention relates to novel veterinary compositions comprising an effective amount of a neonicotinoid compound and an effective amount of a N-arylpyrazole compound. The invention also relates to the use of such compositions for controlling ectoparasites in a non-human mammal.

  本发明涉及新型兽用组合物，该组合物包含有效量的新烟碱化合物和有效量的 N-芳基吡唑化合物。本发明还涉及使用此类组合物控制非人类哺乳动物的体外寄生虫。
• COMPOSITIONS AND USES THEREOF FOR CONTROLLING ECTOPARASITES IN NON-HUMAIN MAMMALS
  申请人：Ceva Santé Animale

  公开号：EP3324955A1

  公开（公告）日：2018-05-30
• [EN] COMPOSITIONS AND USES THEREOF FOR CONTROLLING ECTOPARASITES IN NON-HUMAIN MAMMALS<br/>[FR] COMPOSITIONS ET LEURS UTILISATIONS POUR LUTTER CONTRE LES ECTOPARASITES CHEZ DES MAMMIFÈRES NON HUMAINS
  申请人：CEVA SANTE ANIMALE

  公开号：WO2017017021A1

  公开（公告）日：2017-02-02

  The invention relates to novel veterinary compositions comprising an effective amount of a neonicotinoid compound and an effective amount of a N-arylpyrazole compound. The invention also relates to the use of such compositions for controlling ectoparasites in a non-human mammal.