丙胺氟磷 | 371-86-8

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 中文名称: 丙胺氟磷
• 中文别名: N,N′-氟磷酰二异丙胺；双(异丙氨基)磷酰氟；氟丙胺磷
• 英文名称: mipafox
• 英文别名: N-[fluoro-(propan-2-ylamino)phosphoryl]propan-2-amine
• CAS: 371-86-8
• 化学式: C₆H₁₆FN₂OP
• mdl: MFCD00801119
• 分子量: 182.178
• InChiKey: UOSHUBFBCPGQAY-UHFFFAOYSA-N

物化性质

• 熔点：
  65°
• 沸点：
  125.5°C
• 密度：
  1.2 g/cm3(Temp: 25 °C)
• 颜色/状态：
  Crystals from petroleum ether
• 气味：
  ODORLESS
• 溶解度：
  In water, 80,000 mg/L at 25 °C
• 蒸汽压力：
  0.001 mm Hg at 15 °C
• 稳定性/保质期：

  受热会释放出有毒的氟化物、氧化磷和氧化氮气体。

• 分解：
  When heated to decomposition it emits very toxic fumes of /hydrogen fluoride as well as nitrogen and phosphorus oxides/.

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  4

ADMET

代谢

直接胆碱酯酶抑制剂...包括...米帕fox.../和/化合物发挥直接抑制性行为...它们一旦到达组织，就会迅速被物理和酶解地水解。

/Direct cholinesterase inhibitors/...group includes...mipafox.../and/ compounds exerting direct inhibitory action...are rapidly hydrolyzed both physically and enzymically as soon as they reach tissues.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

神经毒素 - 主要影响运动神经

Neurotoxin - Predominantly motor

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 相互作用

奥德卡布和维拉帕米对人类神经母细胞瘤细胞中米帕fox(371868)诱导的神经病靶酯酶(NTE)活性的影响进行了研究。来源于SK-N-SH人类神经母细胞瘤细胞的SY-5Y(SY5Y)细胞系，在0或5x10(-5)摩尔(M)米帕fox的存在或缺失下，与5x10(-3)M奥德卡布或1x10(-7)M维拉帕米孵育2至10分钟。对这些培养物进行NTE活性的检测。评估了25毫摩尔浓度的异硝基乙酰苯酚(INAP)在米帕fox暴露后2、5或10分钟内重新激活NTE活性的能力。在鸡脑匀浆中也进行了类似的实验。米帕fox在SY5Y细胞和鸡脑匀浆中引起了类似的随时间依赖的NTE活性下降。INAP能够重新激活NTE活性；然而，随着米帕fox和INAP处理之间时间的增加，重新激活的程度降低。奥德卡布和维拉帕米在SY5Y细胞和脑匀浆中抵消了米帕fox的抑制效应。作者得出结论，SY5Y细胞和鸡脑匀浆中的NTE活性，作为有机磷诱导迟发性神经病(OPIDN)的接受模型，受到米帕fox的相似程度抑制。奥德卡布和维拉帕米在两种准备中都对米帕fox诱导的NTE活性抑制产生了抑制作用。

The effects of aldicarb and verapamil on mipafox (371868) induced inhibition of neuropathy-target-esterase (NTE) activity in human neuroblastoma cells were examined. Differentiated SY-5Y (SY5Y) cells, a cell line derived from SK-N-SH-human neuroblastoma cells, were incubated with 0 or 5x10(-5) molar (M) mipafox in the presence or absence of 5x10(-3)M aldicarb or 1x10(-7)M verapamil for 2 to 10 minutes. The cultures were assayed for NTE activity. The ability of 25 millimolar isonitroacetophenone (INAP) to reactivate NTE activity was evaluated 2, 5, or 10 minutes after mipafox exposure. A similar experiment was performed in chicken brain homogenates. Mipafox caused a similar time dependent decrease of NTE activity in SY5Y cells and chicken brain homogenates. INAP was capable of reactivating NTE activity; however, the degree of reactivation decreased with increasing time between mipafox and INAP treatment. Aldicarb and verapamil countered the inhibitory effect of mipafox in both SY5Y cells and the brain homogenates. The authors conclude that NTE activity in SY5Y cells and chicken brain homogenates, the accepted model for organophosphate induced delayed neuropathy (OPIDN), is inhibited to a similar extent by mipafox. Aldicarb and verapamil exert inhibitory effects on the mipafox induced suppression of NTE activity in both preparations.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

甲苯磺酰氟（PMSF）和咪帕氧（Mipafox）的毒性效应，单独或联合使用，在60天大的雄性长埃文斯大鼠中进行研究。动物接受了以下处理：每千克250毫克的PMSF；15mg/kg的Mipafax；250mg/kg的PMSF，4小时后接着15mg/kg的Mipafax；15mg/kg的Mipafox，4小时后接着250mg/kg的PMSF；或者250mg/kg的PMSF，14天后接着15mg/kg的Mipafax。接受单一剂量的动物在给药后1、4、24、48或72小时被牺牲，其他动物在暴露后14到21天被牺牲。进行了测试以确定神经病变、靶酶和颈椎损伤的证据。仅接受PMSF的动物在48小时内无法活动，然后恢复正常活动；没有发生死亡。仅接受Mipafox的动物出现轻度震颤和腹泻；这个组也没有死亡。在PMSF后4小时接受Mipafox的动物有50%的死亡率，在治疗后48小时内无法移动。在Mipafox后4小时接受PMSF的动物出现震颤，在PMSF治疗后消失，使它们在48小时内无法移动；发生了25%的死亡率。在接受PMSF后14天接受Mipafox的动物中没有死亡，尽管动物们同样无法活动。

The toxic effects of phenylmethylsulfonyl-fluoride (329986) (PMSF) and Mipafox (371868), administered either singly or combined, were studied in 60 day old male Long-Evans-rats. Animals were treated with: 250 milligrams per kilogram (mg/kg) PMSF; 15mg/kg Mipafax; 250mg/kg PMSF followed 4 hours later by 15mg/kg Mipafax; 15mg/kg Mipafox followed 4 hours later by 250mg/kg PMSF; or 250mg/kg PMSF followed 14 days later by 15mg/kg Mipafax. Animals receiving single doses of either compound were sacrificed 1, 4, 24, 48, or 72 hours after administration and others were sacrificed 14 to 21 days postexposure. Assays were conducted to determine evidence of neuropathy, target enzyme, and damage to cervical cord. Animals receiving PMSF only were incapacitated for 48 hours and then resumed normal activity; no mortality occurred. Mipafox only animals experienced mild tremors and diarrhea; no mortality occurred in this group either. Animals receiving Mipafox 4 hours after PMSF had a 50 percent mortality rate and remained immobile for 48 hours after treatment. Animals receiving PMSF 4 hours after Mipafox had tremors which were eliminated after PMSF treatment which immobilized them for 48 hours; a 25 percent mortality rate occurred. There were no deaths among animals receiving Mipafox 14 days after PMSF, although the animals were similarly incapacitated.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

紧急和支持性措施。注意：救援人员和卫生保健提供者必须采取措施，防止直接接触受污染受害者的皮肤或衣物，因为可能会发生二次污染和严重疾病，尤其是与高效杀虫剂和神经毒剂接触。保持呼吸道通畅，如有必要，协助通气。特别注意呼吸肌无力；可能会突然发生呼吸停止。如果需要插管，注意神经肌肉阻滞剂和胆碱酯酶抑制剂之间的潜在相互作用。给予补充氧气。如果出现烃吸入性肺炎、癫痫和昏迷，进行治疗。观察无症状患者至少8-12小时，以排除迟发型症状，尤其是在广泛皮肤接触或摄入高度脂溶性的毒剂后。/有机磷和氨基甲酸酯/

Emergency and supportive measures. Caution: rescuers and health care providers must take measures to prevent direct contact with the skin or clothing of contaminated victims, because secondary contamination and serious illness may result, especially with potent pesticides and nerve agents. Maintain an open airway and assist ventilation if necessary. Pay careful attention to respiratory muscle weakness; sudden respiratory arrest may occur. If intubation is required, note potential interactions between neuromuscular blockers and cholinesterase inhibitors. Administer supplemental oxygen. Treat hydrocarbon pneumonitis, seizures, and coma if they occur. Observe asymptomatic patients for at least 8-12 hours to rule out delayed-onset symptoms, especially after extensive skin exposureor ingestion of a highly fat-soluble agent. /Organophosphates and carbamates/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

特定的药物和解毒剂。特异性治疗包括抗胆碱能药物阿托品和酶复活剂普瑞洛辛。根据需要频繁重复给予阿托品……在严重情况下，可能偶尔需要大量累积剂量的阿托品……继续给予阿托品的最重要临床指征是持续的喘息或支气管分泌过多。注意：阿托品将逆转毒蕈碱型效应，但不会逆转烟碱型效应。普瑞洛辛是针对有机磷毒性的特异性解毒剂，它作用于所有受影响的部位（毒蕈碱型、烟碱型，可能还包括中枢神经系统），以恢复酶活性（然而，它不会重新激活血浆胆碱酯酶）。普瑞洛辛应立即给予以逆转肌肉无力和肌束颤动……如果在暴露后的前24小时内开始使用，效果最佳，在酶不可逆磷酸化之前，但即使在晚期给予，也可能有效，特别是在接触高度脂溶性的化合物后。普瑞洛辛通常不推荐用于氨基甲酸盐中毒，因为在这种情况下，胆碱酯酶的抑制是自发性可逆且短暂的。然而，如果确切的药剂未被识别且患者有显著毒性，应经验性地给予普瑞洛辛。/有机磷和氨基甲酸盐/

Specific drugs and antidotes. Specific treatment includes the antimuscarinic agent atropine and the enzyme reactivator pralidoxime. Give atropine ... repeated frequently as needed. Large cumulative doses of atropine ... may occasionally be required in severe cases. The most clinically important indication for continued atropine administration is persistent wheezing or bronchorrhea. Note: Atropine will reverse muscarinic but not nicotinic effects. Pralidoxime is a specific antidote for organophosphate toxicity, that acts to regenerate the enzyme activity at all affected sites (muscarinic, nicotinic, and probably CNS; however, it does not reactivate plasma cholinesterase). Pralidoxime should be given immediately to reverse muscular weakness and fasciculations... . It is most effective if started within the first 24 hours of the exposure before irreversible phosphorylation of the enzyme, but may still be effective if given late, particularly after exposure to highly lipid soluble compounds. Pralidoxime is not generally recommended for carbamate intoxication, because in such cases the cholinesterase inhibition is spontaneously reversible and short-lived. However, if the exact agent is not identified and the patient has significant toxicity, pralidoxime should be given empirically. /Organophosphates and carbamates/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  T+
• 危险类别码：
  R45,R13

制备方法与用途

类别：农药

• 毒性分级：高毒

• 急性毒性：

  • 大鼠经腹腔 LD50: 90 毫克/公斤
  • 小鼠经腹腔 LD50: 14 毫克/公斤

• 可燃性危险特性：受热时能释放有毒的氟化物、氧化磷和氧化氮气体

• 储运特性：

  • 库房需通风、低温干燥
  • 与食品原料分开储存和运输

• 灭火剂：

  • 二氧化碳
  • 砂土
  • 泡沫
  • 干粉

反应信息

• 作为反应物：
  描述：

  丙胺氟磷 在 Cu(N,N,N',N'-tetramethylethylenediamine)(ClO₄)2 、 水 作用下， 生成 N,N'-Diisopropylphosphorodiamidic acid
  参考文献：
  名称：

  Marjit, D. N.; Raza, S. K.; Saxena, Chhaya, Journal of the Indian Chemical Society, 1992, vol. 69, # 10, p. 654 - 655

  摘要：

  DOI：
• 作为产物：
  描述：

  异丙胺 在 potassium fluoride 、 氯仿 、 水 、 三氯氧磷 作用下， 生成 丙胺氟磷
  参考文献：
  名称：

  DE895228

  摘要：

  公开号：

文献信息

• [EN] MICROBIOCIDAL OXADIAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'OXADIAZOLE MICROBIOCIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2017157962A1

  公开（公告）日：2017-09-21

  Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially fungicides.

  式(I)的化合物，其中取代基如权利要求1所定义，作为杀虫剂特别是杀菌剂有用。
• Thieno-pyrimidine compounds having fungicidal activity
  申请人：Brewster Kirkland William

  公开号：US20070093498A1

  公开（公告）日：2007-04-26

  The present invention relates to thieno[2,3-d]-pyrimidine compounds having fungicidal activity.

  本发明涉及具有杀真菌活性的噻吩[2,3-d]-嘧啶化合物。
• [EN] INSECTICIDAL TRIAZINONE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRIAZINONE INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2013079350A1

  公开（公告）日：2013-06-06

  Compounds of the formula (I) or (I'), wherein the substituents are as defined in claim 1, are useful as pesticides.

  式(I)或(I')的化合物，其中取代基如权利要求1所定义的那样，可用作杀虫剂。
• Novel insecticides
  申请人：Syngenta Participations AG

  公开号：EP2540718A1

  公开（公告）日：2013-01-02

  Compounds of formula I wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula I can be used as insecticides and can be prepared in a manner known per se.

  式I的化合物 其中取代基如权利要求1所定义，并且式I化合物的农药可接受盐以及所有立体异构体和互变异构形式可用作杀虫剂，并且可以按照已知的方法制备。
• Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
  申请人：Dow AgroSciences LLC

  公开号：US20180279612A1

  公开（公告）日：2018-10-04

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions against such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫具有杀虫效用的分子领域，用于生产此类分子的过程，用于此类过程的中间体，含有此类分子的杀虫组合物，以及使用此类杀虫组合物对抗此类害虫的过程。这些杀虫组合物可以用作螨虫剂、杀虫剂、螨虫剂、软体动物杀虫剂和线虫杀虫剂。本文件披露了具有以下式（“式一”）的分子。