乙基溴硫磷 | 4824-78-6

• 物质功能分类: 化学农药原药 - 杀虫剂 - 有机氯杀虫剂
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫代磷酸及其衍生物
• 中文名称: 乙基溴硫磷
• 中文别名: o-(4-溴-2，5-二氯苯基)-o，o-二乙基硫代磷酸酯；乙溴硫磷
• 英文名称: Bromophos ethyl
• 英文别名: Bromophos-ethyl；(4-bromo-2,5-dichlorophenoxy)-diethoxy-sulfanylidene-λ5-phosphane
• CAS: 4824-78-6
• 化学式: C₁₀H₁₂BrCl₂O₃PS
• 分子量: 394.053
• InChiKey: KWGUFOITWDSNQY-UHFFFAOYSA-N

物化性质

• 沸点：
  122.5°C
• 密度：
  1.590
• 闪点：
  100 °C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 颜色/状态：
  Colorless to pale yellow liquid
• 蒸汽压力：
  4.6X10-5 mm Hg @ 30 °C (6.1 mPa at 30 °C)
• 稳定性/保质期：
  在常温常压下，该物质是稳定的。
• 腐蚀性：
  Non-corrosive
• 折光率：
  Index of refraction: 1.5600 at 20 °C/D
• 碰撞截面：
  166.45 Ų [M+H]+; 178.4 Ų [M+HCOO]-
• 保留指数：
  2075;2097;2080.9;2077.1;2096.8

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

代谢

血浆和组织的酶负责将有机磷化合物水解成相应的磷酸和磷onic酸。然而，氧化酶也参与一些有机磷化合物的代谢。抗胆碱酯酶制剂

Plasma & tissue enzymes are responsible for hydrolysis /of organophosphorus compounds/ to the corresponding phosphoric & phosphonic acids. However, oxidative enzymes are also involved in the metabolism of some organophosphorus compounds. /Anticholinesterase agents/

来源:Hazardous Substances Data Bank (HSDB)

代谢

有机磷抗胆碱酯酶剂在体内被一组称为A-酯酶或对氧磷酶的酶水解。这些酶存在于血浆和肝脏内质网中，能够水解大量的有机磷化合物...通过分裂无水物、P-F、P-CN或酯键。/抗胆碱酯酶剂/

The organophosphorus anticholinesterase agents are hydrolyzed in the body by a group of enzymes known as A-esterases or paroxonase. The enzymes are found in plasma and in the hepatic endoplasmic reticulum & can hydrolyze a large number of organophosphorus compounds ... by splitting the anhydride, P-F, P-CN, or ester bond. /Anticholinesterase agents/

来源:Hazardous Substances Data Bank (HSDB)

代谢

溴磷通过酶促降解生成了4-溴-2,5-二氯苯基磷酰硫代酸酯。当使用猪或小鼠肝脏制剂时，这是唯一形成的产物。谷胱甘肽刺激了该反应。当与4摩尔氢氧化钠一起孵化时，形成了二甲基硫代磷酰氧。没有观察到去甲基溴磷。当与pH为10和11的缓冲液一起孵化时，确实形成了芳基硫代磷酰氧。/溴磷/

Bromophos was enzymatically degraded to 4-bromo-2,5-dichlorophenyl phosphorothionate. This was the only product formed when hog or mouse liver preparations were used. Glutathione stimulated the reaction. When incubated with 4 molor sodium hydroxide, dimethyl phosphorothionate formed. No desmethyl bromophos was observed. When incubated with buffers of pH 10 and 11, the aryl phosphorothionate did form. /Bromophos/

来源:Hazardous Substances Data Bank (HSDB)

代谢

溴磷的氧化态被羊、兔、大鼠和鸡的血浆缓慢水解。/溴磷/

The oxon of bromophos was hydrolyzed rather slowly by plasma of sheep, rabbit, rat, and chicken. /Bromophos/

来源:Hazardous Substances Data Bank (HSDB)

代谢

来自使用溴磷乙酯浸渍和喷雾控制牛蜱地区的动物肉类脂肪分析检测到了一种残留物，被确认为O,O-二乙基-O-(2,5-二氯苯基)硫代磷酸酯。

Analyses of meat fats of animals from areas that use bromophos-ethyl dips and sprays to control cattle ticks have detected a residue identified as O,O-diethyl O-(2,5-dichlorophenyl)phosphorothionate.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

其他毒物 - 有机磷酸酯

Other Poison - Organophosphate

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

毒理性

• 毒性数据

LCLo（大鼠）= 16.6 ppm/2小时

LCLo (rat) = 16.6 ppm/2h

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

毒理性

• 相互作用

抗胆碱酯酶（有机磷）杀虫剂拮抗极化肌肉松弛剂。吩噻嗪类/和硫杂蒽类/：...可能增强有机磷杀虫剂的有毒效果。/杀虫剂，有机磷/

ANTICHOLINESTERASE (ORGANOPHOSPHORUS) INSECTICIDES ANTAGONIZE POLARIZING MUSCLE RELAXANTS. PHENOTHIAZINES /AND THIOXANTHENES/: ... MAY ENHANCE TOXIC EFFECTS OF ORGANOPHOSPHORUS INSECTICIDES. /INSECTICIDES, ORGANOPHOSPHORUS/

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。根据中毒的严重程度，可能需要从非常低的剂量到高达300毫克/日的阿托品，甚至可能需要持续输注。阿托品抗毒疗法的目的是拮抗乙酰胆碱在具有毒蕈碱受体的末梢器官上的过量浓度效应。阿托品不能重新激活胆碱酯酶酶或加速有机磷的处置。如果组织中有机磷浓度仍然很高，阿托品的效果消失后可能会再次出现中毒。阿托品对毒蕈碱表现有效，但对烟碱作用无效，尤其是肌肉无力和抽搐以及呼吸抑制。尽管有这些局限性，阿托品在有机磷中毒中常常是救命药物。对阿托品测试剂量的良好反应（成人为1毫克，12岁以下儿童为0.01毫克/千克）可以帮助区分抗胆碱酯酶剂中毒与其他状况。然而，没有反应，并且没有阿托品化的证据（阿托品耐药性）是更严重中毒的典型特征。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. Depending on the severity of poisoning, doses of atropine ranging from very low to as high as 300 mg/day may be required, or even continuous infusion. The objective of atropine antidotal therapy is to antagonize the effects of excessive concentrations of acetylcholine at end-organs having muscarinic receptors. 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. Favorable response to a test dose of atropine (1 mg in adults, 0.01 mg/kg in children under 12 years) can help differentiate poisoning by anticholinesterase agents from other conditions. However, lack of response, with no evidence of atropinization (atropine refractoriness) is typical of more severe 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

有机磷农药的皮肤吸收率可能会受到所使用溶剂的影响。

The rate of dermal absorption /of organophosphorus pesticides/ may be ... influenced by the solvent used. /Organophosphorus pesticides/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

有机磷杀虫剂与氯化杀虫剂相比，能够被迅速代谢和排出体外，并且不会在身体组织中显著储存。/有机磷杀虫剂/

... The organophosphorus insecticides are, in contrast to the chlorinated insecticides, rapidly metabolized & excreted and are not appreciably stored in body tissues. /Organophosphorus insecticides/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

许多有机磷杀虫剂会通过牛奶排出体外... /有机磷杀虫剂/

Many of the organophosphorus insecticides are excreted in the milk ... /Organophosphorus insecticides/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

有机磷化合物被吸收后，大部分会以水解产物的形式通过尿液排出体外。/抗胆碱酯酶剂/

Following their absorption, most organophosphorus cmpd are excreted ... as hydrolysis products in the urine. /Anticholinesterase agents/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(a)
• 危险品标志：
  N,T
• 安全说明：
  S28,S36/37,S45,S60,S61
• 危险类别码：
  R21,R50/53,R25
• WGK Germany：
  3
• 海关编码：
  29201900
• RTECS号：
  TE7000000
• 包装等级：
  II
• 危险类别：
  6.1(a)

制备方法与用途

类别：农药

毒性分级：高毒

急性毒性：

• 口服-大鼠 LD50: 52 毫克/公斤
• 口服-小鼠 LD50: 210 毫克/公斤

可燃性危险特性：受热分解产生有毒的氧化磷、氧化硫及卤化物气体

储运特性：

• 库房应通风、低温和干燥
• 储存时需与食品原料分开

灭火剂：

• 砂土
• 干粉
• 泡沫

反应信息

• 作为反应物：
  描述：

  乙基溴硫磷 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.08h， 生成 O,O-Diethyl-O-(2,5-dichlor-4-bromphenyl)-phosphat
  参考文献：
  名称：

  Dimethyldioxirane conversion of phosphine sulfides and phosphorothioates into their corresponding oxygen analogues

  摘要：

  DOI：

  10.1016/s0040-4039(00)89065-6

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。
• THIENYLPYRIDYLCARBOXAMIDES
  申请人：Dunkel Ralf

  公开号：US20110105564A1

  公开（公告）日：2011-05-05

  Novel thienylpyridylcarboxamides of the formula (I) The present application is also directed to a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and also novel intermediates and their preparation.

  新型噻吩基吡啶基羧酰胺的化学式（I） 本申请还涉及多种制备这些化合物的方法，以及它们用于控制不受欢迎的微生物的用途，还有新颖的中间体及其制备。
• [EN] ISOXAZOLINE DERIVATIVES AS INSECTICIDES<br/>[FR] DÉRIVÉS D'ISOXAZOLINE EN TANT QU'INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2011101402A1

  公开（公告）日：2011-08-25

  The present invention relates to compounds formula (I), wherein P is P1, P2, heterocyclyl or heterocyclyl substituted by one to five Z; and wherein A1, A2, A3, A4, G1, R1, R2, R3, R4, R5, R6, R17, R18, R19 and R20 are as defined in claim 1; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (I), to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising the compounds of formula (I) and to methods of using the compounds of formula (I) to control insect, acarine, nematode and mollusc pests.

  本发明涉及化合物式（I），其中P为P1、P2、杂环烷基或被一到五个Z取代的杂环烷基；以及其中A1、A2、A3、A4、G1、R1、R2、R3、R4、R5、R6、R17、R18、R19和R20如权利要求1中所定义；或其盐或N-氧化物。此外，本发明涉及制备化合物式（I）的过程和中间体，包括化合物式（I）的杀虫剂、杀螨剂、杀线虫剂和杀软体动物剂组合物，以及使用化合物式（I）控制昆虫、螨虫、线虫和软体动物害虫的方法。

表征谱图