丁酯膦 | 126-22-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 丁酯膦
• 中文别名: 布托酯
• 英文名称: (1-butyryloxy-2,2,2-trichloro-ethyl)-phosphonic acid dimethyl ester
• 英文别名: (1-Butyryloxy-2,2,2-trichlor-aethyl)-phosphonsaeure-dimethylester；Dimethyl 1-(butyryloxy)-2,2,2-trichloroethylphosphonate；O,O-dimethyl-2,2,2-trichloro-1-n-butyryloxyethyl phosphonate；butonate；O,O-Dimethyl-(1-n-butyryl-oxy-2,2,2-trichlorethyl)-phosphonat；O,O-Dimethyl-1-butyryloxy-2,2,2-trichlorethylphosphonat；(2,2,2-trichloro-1-dimethoxyphosphorylethyl) butanoate
• CAS: 126-22-7
• 化学式: C₈H₁₄Cl₃O₅P
• 分子量: 327.529
• InChiKey: BKAQXYNWONVOAX-UHFFFAOYSA-N

物化性质

• 沸点：
  bp0.5 129°
• 密度：
  1.390±0.06 g/cm3(Predicted)
• 颜色/状态：
  Colorless, somewhat oily liquid
• 气味：
  Slight ester odor
• 溶解度：
  In water, 290 mg/L at 25 °C (est)
• 蒸汽压力：
  1.1X10-4 mm Hg at 25 °C (est)
• 稳定性/保质期：

  Stable to light but decomposes above 150 °C

• 分解：
  When heated to decomposition it emits highly toxic fumes of /phosphorus oxides and hydrogen chloride/.
• 折光率：
  Index of refraction = 1.4707
• 保留指数：
  1693.2

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

ADMET

代谢

在植物中，丁酮酸通过脱酰化途径的氯酚和脱甲基氯酚以及作为次要代谢物的敌敌畏进行代谢，并通过脱甲基丁酮酸进行脱甲基化。

In plants, butonate was metabolized by deacylation via trichlorphon and demethyltrichlorphon with dichlorvos as minor metabolite and by demethylation via demethylbutonate.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在热血动物的肝脏和血液中，丁酸主要通过P-C键的水解降解，形成二甲基磷酸。在体外血液中也会形成少量的去甲基丁酸。丁酸也会被鱼类水解。在昆虫中，有机酸通过酯酶的作用被移除，形成三氯酚（灭害灵），后者又被代谢为DDVP。

In the liver and blood of warm blooded animals, butonate was degraded primarily by hydrolysis of P-C bond with formation of dimethylphosphate. Small amount of the desmethylbutonate also formed in blood in vitro. Butonate was also hydrolyzed by fish. In insects, the organic acid was removed by esterase action and trichlorofon (Dipterex) was formed, which in turn was metabolized to DDVP.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在非生物介质中，丁酸酯在pH小于5.5时降解为三氯磷、脱甲基三氯磷和脱甲基丁酸酯，而在pH大于5.5时，更倾向于降解为乙烯基丁酸酯、脱甲基丁酸酯和脱甲基乙烯基丁酸酯，并伴有少量的三氯磷。

In aq nonbiological media, butonate was degraded at pH less than 5.5 to trichlorphon, demethyltrichlorphon, and demethylbutonate, at pH greater than 5.5 preferably to vinylbutonate, demethylbutonate, and demethylvinylbutonate with traces of trichlorphon.

来源:Hazardous Substances Data Bank (HSDB)

代谢

含有磷的杀虫剂及其代谢物对血液胆碱酯酶活性的影响通过测定乙酰胆碱水解过程中pH的变化来衡量。纳尔、敌敌畏和敌百虫的抑制作用比丁氧基乙酸强。

The effects of Phosphorus containing insecticides and their metabolites on blood cholinesterase activity were measured by determining the change in pH during hydrolysis of acetylcholine. Naled, dichlorvos, and trichlorfon were stronger inhibitors than butonate.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

其他毒物 - 有机磷

Other Poison - Organophosphate

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

毒理性

• 解毒与急救

基本治疗：建立专利气道。如有必要，进行吸痰。可能需要积极的气道控制。观察呼吸不足的迹象，如有必要，协助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，并在必要时治疗...。监测休克，并在必要时治疗...。预见并治疗癫痫发作...。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用生理盐水连续冲洗每只眼睛...。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的干呕反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释。给予活性炭...。/有机磷及其相关化合物/

Basic treatment: Establish a patent airway. Suction if necessary. Aggressive airway control may be needed. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Organophosphates and Related Compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

高级治疗：对于失去意识或有严重肺水肿的患者，考虑进行口咽或鼻咽插管以控制气道。使用气囊-阀-面罩装置的正压通气技术可能有益。监测心率和必要时治疗心律失常。开始静脉输液，使用5%葡萄糖生理盐水维持开放，最小流量/慢速复苏程序。如果出现低血容量的迹象，使用乳酸钠林格氏液。给予阿托品。在给予阿托品前纠正低氧血症。给予氯磷定（2 PAM）。治疗抽搐时，要确保充分阿托品化和纠正低氧血症。很少需要使用地西泮。对于伴有低血容量迹象的低血压，谨慎给予液体，并在正常血容量时考虑使用血管加压药物。注意液体过载的迹象。使用丙美卡因氢氯化物协助眼部冲洗。/有机磷和相关化合物/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or has severe pulmonary edema. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Administer atropine. Correct hypoxia before giving atropine ... . Administer pralidoxime chloride (2 PAM). ... . Treat seizures with adequate atropinization and correction of hypoxia. Rarely is diazepam necessary ... . For hypotension with signs of hypovolemia, administer fluid cautiously and consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organophosphates and Related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

气道保护。确保呼吸道通畅。必要时对患者进行气管插管，并使用大口径吸痰设备吸出分泌物。如果呼吸抑制，通过机械辅助肺通气给予氧气。在给予阿托品之前尽可能改善组织氧合，以最小化心室颤动的风险。在严重中毒的情况下，可能需要机械支持肺通气数天。/有机磷农药/

Airway protection. Insure that a clear airway exists. Intubate the patients and aspirate the secretions with a large-bore suction device if necessary. Administer oxygen by mechanically assisted pulmonary ventilation if respiration is depressed. Improve tissue oxygenation as much as possible before administering atropine, so as to minimize the risk of ventricular fibrillation. In severe poisonings, it may be necessary to support pulmonary ventilation mechanically for several days. /Organophosphate pesticides/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

硫酸阿托品。如果不能静脉注射，可以通过静脉或肌肉注射硫酸阿托品。请记住，如果初次静脉通路难以获得，阿托品可以通过气管内导管给药。...阿托品不能重新激活胆碱酯酶酶或加速有机磷的处置。如果组织中的有机磷浓度在阿托品效果消失时仍然很高，可能会再次出现中毒症状。阿托品对毒蕈碱表现有效，但对烟碱作用无效，特别是肌肉无力和抽搐以及呼吸抑制。尽管有局限性，阿托品在有机磷中毒中常常是救命药。...据报道，雾化阿托品的辅助使用可以改善呼吸窘迫，减少支气管分泌物，并增加氧合。/有机磷农药/

Atropine sulfate. Administer atropine sulfate intravenously, or intramuscularly if intravenous injection is not possible. Remember that atropine can be administered through an endotracheal tube if initial IV access if difficult to obtain. ... Atropine does not reactivate the cholinesterase enzyme or accelerate disposition of organophosphate. Recrudescence of poisoning may occur if tissue concentrations of organophosphate remain high when the effect of atropine wears off. Atropine is effective against muscarinic manifestations, but it is ineffective against nicotinic actions, specifically muscle weakness and twitching, and respiratory depression. Despite the limitations, atropine is often a life-saving agent in organophosphate poisonings. ... The adjunctive use of nebulized atropine has been reported to improve respiratory distress, decrease bronchial secretions, and increase oxygenation. /Organophosphate pesticides/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

MAC值为2毫克/立方米。丁酸盐在水果和蔬菜中的半衰期为0.5-1.5天。一般作物处理后的必要等待期为3-7天，用于婴儿食品和食疗制剂的作物等待期为10天。

... The MAC is 2 mg/cu m. The half-life of butonate in fruits and vegetables is 0.5-1.5 days. The necessary waiting period after treatment is 3-7 days for general-purpose crops, and 10 days for crops to be used in baby food and dietetic preparations.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 海关编码：
  2931900045
• 储存条件：
  请将物品存放在通风、低温和干燥的地方。

制备方法与用途

类别：农药
毒性分级：中毒
急性毒性：口服-大鼠 LD50: 1100 毫克/公斤；口服-小鼠 LD50: 760 毫克/公斤
可燃性危险特性：燃烧时产生有毒的硫氧化物、磷氧化物和氯化物气体
储运特性：需存放在通风低温干燥的库房中，并与食品原料分开存放和运输
灭火剂：干粉、泡沫、砂土

反应信息

• 作为反应物：
  描述：

  丁酯膦 在 sodium iodide 作用下， 以 丁酮 为溶剂， 生成 Butyric acid 2,2,2-trichloro-1-(hydroxy-methoxy-phosphoryl)-ethyl ester
  参考文献：
  名称：

  Schneider,P.; Fischer,G.W., Journal fur praktische Chemie (Leipzig 1954), 1977, vol. 319, p. 391 - 398

  摘要：

  DOI：
• 作为产物：
  描述：

  敌百虫 、 丁酰氯 在 乙醚 、 三乙胺 作用下， 生成 丁酯膦
  参考文献：
  名称：

  Nikonorow, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1958, p. 1340,1342;engl.Ausg.S.1292,1294

  摘要：

  DOI：

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。