氟虫腈酰胺 | 205650-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 氟虫腈酰胺
• 中文别名: 氟虫腈
• 英文名称: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carboxamide
• 英文别名: 5-amino-3-amide-1-(2,6-dichloro-4-trifluoromethyl)phenyl-4-trifluoromethylsulfinylpyrazole；amide-fipronil；fipronil amide；fipronil-amide；5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carboxamide
• CAS: 205650-69-7
• 化学式: C₁₂H₆Cl₂F₆N₄O₂S
• 分子量: 455.168
• InChiKey: OPPWTDFHAFPGOT-UHFFFAOYSA-N

物化性质

• 熔点：
  224 °C
• 沸点：
  496.4±45.0 °C(Predicted)
• 密度：
  1.97±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  11

安全信息

• WGK Germany：
  3

反应信息

• 作为产物：
  描述：

  氟虫腈 在 水 作用下， 以 甲醇 为溶剂， 生成 氟虫腈酰胺
  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

• [EN] 1-(AZOLIN-2-YL)AMINO-1,2-DIPHENYLETHANE COMPOUNDS FOR COMBATING ANIMAL PESTS<br/>[FR] COMPOSÉS 1-(AZOLIN-2-YL)AMINO-1,2-DIPHÉNYLÉTHANE POUR LUTTER CONTRE LES ANIMAUX NUISIBLES
  申请人：BASF SE

  公开号：WO2009004032A1

  公开（公告）日：2009-01-08

  The present invention relates to 1-(azolin-2-yl)amino-1,2-diphenylethane compounds of the formula I and to their salts which are useful for combating animal pests. The invention also relates to a method for controlling animal pests by using these compounds, to seed and to an agricultural and veterinary composition comprising said compounds, wherein A is a radical of formulae A.1 or A.2 wherein # denotes the bond to the remaining compound of formula I, X is selected from O, S and NRx, R1 is selected from the group consisting of -ORA, -NRB1RB2, -C(=O)-RC, -C(=O)-ORD, -C(=O)-SRE, -C(=O)-NRB1RB2', -C(=S)-RC', -C(=S)-ORD', -C(=S)-SRE', -C(=S)-NRB1RB2, -C(=NR1a)-RC', -C(=NR1b)-ORD', -C(=NR1c)-SRE', -C(=NR1d)-NRB1RB2, -S(=O)-RF, -S(=O)2-RG, -S(=O)2-NRB1RB2', -P(=O)RH1RH2, -P(=S)RH1RH2, -B-C(=O)-RI, -B-O-C(=O)-RI, -B-S-C(=O)-RI, -B-N(RJ)-C(=O)-RK, -B-C(=S)-RK, -B-O-C(=S)-RK, -B-S-C(=S)-RK, -B-N(RJ)-C(=S)-RK, C1-C8-alkenyl, C1-C8-alkynyl, C3-C8-cycloalkyl, which is unsubstituted or may carry 1 to 4 substituents R1e, naphthyl, which is unsubstituted or may carry 1 to 4 substituents R1f, a saturated or partially unsaturated heterocycle, which is unsubstituted or may carry 1 to 4 substituents R1g, hetaryl, which is unsubstituted or may carry 1 to 4 substituents R1h, and C1-C6-alkyl, which carries a radical selected from the group consisting of -NR1iR1j, C1-C4-alkoxycarbonyl, C3-C8-cycloalkyl, aryl, aryloxy, arylthio, heterocyclyl, heterocyclyloxy and heterocyclylthio, R2, R3, R4, R5, R6 and R7 are each independently hydrogen, halogen, OH, SH, NH2, SO3H, COOH, cyano, nitro, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino etc.

  本发明涉及公式I的1-(咪唑啉-2-基)氨基-1,2-二苯乙烷化合物及其盐，用于防治动物害虫。本发明还涉及使用这些化合物控制动物害虫的方法，种子以及包含所述化合物的农业和兽医组合物，其中A是公式A.1或A.2的基团，其中#表示与公式I的其余化合物的键合，X从O、S和NRx中选择，R1从由-ORA、-NRB1RB2、-C（=O）-RC、-C（=O）-ORD、-C（=O）-SRE、-C（=O）-NRB1RB2'、-C（=S）-RC'、-C（=S）-ORD'、-C（=S）-SRE'、-C（=S）-NRB1RB2、-C（=NR1a）-RC'、-C（=NR1b）-ORD'、-C（=NR1c）-SRE'、-C（=NR1d）-NRB1RB2、-S（=O）-RF、-S（=O）2-RG、-S（=O）2-NRB1RB2'、-P（=O）RH1RH2、-P（=S）RH1RH2、-B-C（=O）-RI、-B-O-C（=O）-RI、-B-S-C（=O）-RI、-B-N（RJ）-C（=O）-RK、-B-C（=S）-RK、-B-O-C（=S）-RK、-B-S-C（=S）-RK、-B-N（RJ）-C（=S）-RK、C1-C8-烯丙基、C1-C8-炔基、C3-C8-环烷基，未取代或可携带1至4个取代基R1e，萘基，未取代或可携带1至4个取代基R1f，饱和或部分不饱和的杂环，未取代或可携带1至4个取代基R1g，杂芳基，未取代或可携带1至4个取代基R1h，以及C1-C6-烷基，携带从由-NR1iR1j、C1-C4-烷氧羰基、C3-C8-环烷基、芳基、芳氧基、芳硫基、杂环基、杂环氧基和杂环硫基选择的基团，R2、R3、R4、R5、R6和R7各自独立地为氢、卤素、OH、SH、NH2、SO3H、COOH、氰基、硝基、C1-C6-烷基、C1-C6-烷氧基、C1-C6-烷基氨基等。
• Design, One-Step Highly Selective Synthesis and Enhancing Insecticidal Activity and Photo-Self-Degradation of Phenylpyrazole Esterified Derivatives as GABA and nACh Receptor Inhibitors
  作者：Huan Liu、Zhongda Wu、Yanting Du、Quan Zhou、Lianqing Chen、Shiwei Jin

  DOI：10.1021/acs.jafc.3c04645

  日期：2024.1.31

  phenylpyrazole esterified derivatives (PEs) were synthesized using an improved Pinner reaction with high selectivity. Lewis acid catalysis was employed in a one-step solvent-thermal method to convert the cyano group of fipronil into an ester unit. FeCl3 was found to exhibit the highest selectivity for PEs synthesis, yielding PEs at 96.4%, with the byproduct being phenylpyrazole amide (PE0) at 2.1%. Initial biological

  为了寻求对GABA受体具有高活性和独特作用方式的新型杀虫剂，采用改进的Pinner反应以高选择性合成了一系列苯基吡唑酯化衍生物（ PE ）。采用路易斯酸催化一步溶剂热法将氟虫腈的氰基转化为酯单元。 FeCl 3对PE合成具有最高的选择性， PE产率为 96.4%，副产物为苯基吡唑酰胺 ( PE 0 )，产率为 2.1%。初步生物测定表明，与氟虫腈相比，目标化合物对小菜蛾和粘虫具有优异的杀虫活性。特别是，较小和较短的酯单元PE 3 、 PE 5和PE 8对小菜蛾的杀虫活性比氟虫腈高 2-2.5 倍。与酰胺和酰腙单元相比，酯单元的更高活性可归因于PE的脂溶性增强。此外，这可能是由于PEs对神经递质nACh的影响或钙离子和氯离子与酯的-C=O和-O-键的配位，阻断了氯离子通道。通过反相高效液相色谱 ( HPLC ) 证实了疏水性参数，表明PE的酯单元赋予了增强的亲脂性。 分子对接和CoMFA分析
• 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。
• Pesticidal mixtures comprising cyanosulfoximine compounds
  申请人：BASF SE

  公开号：US11033028B2

  公开（公告）日：2021-06-15

  The invention relates to pesticidal mixtures comprising as active compounds 1) at least one cyanosulfoximine compound I of the formula I wherein R1, R2 and G are defined in the description; and 2) at least one active compound II selected from a group A comprising acteylcholine esterase inhibitors, GABA-gated chloride channel antagonists, sodium channel modulators, nicotinic acetylcholine receptor agonists/antagonists, chloride channel activators, juvenile hormone mimics, compounds affecting the oxidative phosphorylation, inhibitors of the chitin biosynthesis, moulting disruptors, inhibitors of the MET, voltage-dependent sodium channel blockers, inhibitors of the lipid synthesis and other compounds as defined in the description, in synergistically effective amounts. The invention relates further to methods and use of these mixtures for combating insects, arachnids or nematodes in and on plants, and for protecting such plants being infested with pests and also for protecting seeds.

  本发明涉及杀虫混合物，其活性化合物包括 1) 至少一种式 I 的氰基亚磺酰亚胺化合物 I 其中 R1、R2 和 G 的定义见说明； 和 2) 至少一种选自 A 组的活性化合物 II，该组包括放线胆碱酯酶抑制剂、GABA 门控氯离子通道拮抗剂、钠通道调节剂、烟碱乙酰胆碱受体激动剂/拮抗剂、氯离子通道激活剂、幼年激素模拟物、影响氧化磷酸化的化合物、甲壳素生物合成抑制剂、蜕皮干扰素、MET 抑制剂、电压依赖性钠通道阻滞剂、脂质合成抑制剂和说明中定义的其他化合物，且用量协同有效。 本发明还涉及使用这些混合物防治植物体内和植物上的昆虫、蛛形纲动物或线虫，保护被害虫侵扰的植物以及保护种子的方法和用途。