毒鼠磷 | 4104-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 毒鼠磷
• 中文别名: O,O-双(4-氯苯基)(1-亚氨基乙基)硫代磷酰胺；O,O-双(对氯苯基)(1-亚胺乙基)硫代磷酰胺酯；O,O-双(对氧苯基)-N-1-亚氨基乙基硫代磷酰胺；O,O-二-4-氯苯基-N-亚氨乙酰基硫代磷酰胺酯；毒鼠灵；毒鼠磷；O,O-双（对氧苯基）-N-1-亚氨基乙基硫代磷酰胺
• 英文名称: gophacide
• 英文别名: O,O-bis(p-chlorophenyl)acetimidoyl-phosphoroamidothioate；phosacetim；N'-bis(4-chlorophenoxy)phosphinothioylethanimidamide
• CAS: 4104-14-7
• 化学式: C₁₄H₁₃Cl₂N₂O₂PS
• 分子量: 375.215
• InChiKey: XIBXUAZIZXDFTG-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  纯品为白色结晶，熔点为107～109℃。它易溶于二氯甲烷，微溶于乙醇、氯仿、苯和醚，不溶于水。在室温下稳定，不易吸潮。工业品通常呈现浅粉色或浅黄色粉末状，纯度一般在80%以上。

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

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

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，以排除迟发性症状的出现，尤其是在大面积皮肤接触或摄入高度脂溶性的毒剂之后。/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之后。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)

毒理性

• 解毒与急救

去污。注意：处理严重污染的受害者时，救援人员必须穿上化学防护服和手套。如果存在像二甲苯或甲苯这样的溶剂的重度液体污染，应在户外或通风量大的房间进行衣物去除和受害者去污。1. 皮肤。去除所有污染的衣物，并用肥皂和水清洗暴露区域，包括头发和指甲下。用大量的温水或盐水冲洗暴露的眼睛。2. 吞咽。a. 就医前。如果有的话，给予活性炭。不要催吐，因为存在毒性突然发作的风险。b. 医院。给予活性炭（如果患者已经有腹泻，则不需要泻药）。对于大量最近吞咽的情况，进行洗胃。/有机磷和氨基甲酸酯/

Decontamination. Note: Rescuers must wear chemical-protective clothing and gloves when handling a grossly contaminated victim. If there is heavy liquid contamination with a solvent such as xylene or toluene, clothing removal and victim decontamination should be carried out outdoors or in a room with high-flow ventilation. 1. Skin. Remove all contaminated clothing and wash exposed areas with soap and water, including the hair and under the nails. Irrigate exposed eyes with copious tepid water or saline. 2. Ingestion. a. Prehospital. Administer activated charcoal, if available. Do not induce vomiting because of the risk of abrupt onset of toxicity. b.Hospital. Administer activated charcoal (cathartics are not necessary if the patient already has diarrhea). Perform gastric lavage for large recent ingestions. /Organophosphates and carbamates/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

增强消除。由于分布体积大，通常不推荐透析和血液灌流... /有机磷和氨基甲酸酯/

Enhanced elimination. Dialysis and hemoperfusion are not generally indicated because of the large volume of distribution... /Organophosphates and carbamates/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

有机磷农药通过消化道的粘膜、呼吸系统和皮肤迅速被吸收进入人体，并通过血液传输到各种身体组织。

Organophosphorus pesticides are rapidly absorbed into the body through the mucous membrane of the digestive tract, the respiratory system, & the skin, and are conveyed by the blood to various body tissues. /Organophosphorus pesticides/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

有机磷农药通过消化道的粘膜、呼吸系统以及皮肤迅速被吸收进入人体，并由血液传送到各种身体组织。

Organophosphorus pesticides are rapidly absorbed into the body through the mucous membrane of the digestive tract, the respiratory system, & the skin, and are conveyed by the blood to various body tissues. /Organophosphorus pesticides/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

有机磷农药通过消化道的粘膜、呼吸系统和皮肤迅速被吸收进入人体，并通过血液传送到各种身体组织。

Organophosphorus pesticides are rapidly absorbed into the body through the mucous membrane of the digestive tract, the respiratory system, & the skin, and are conveyed by the blood to various body tissues. /Organophosphorus pesticides/

来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

制备方法

以对氯苯酚、三氯硫磷、盐酸乙脒和三乙胺为原料，按以下步骤合成：将三氯硫磷溶于苯中，搅拌。在常温下缓缓滴入对氯苯酚、苯及三乙胺的混合液，并控制摩尔配比为三氯硫磷：对氯苯酚：三乙胺=1:2:2。加毕后保温，在15-25℃反应0.5小时。随后，用水洗涤，静置，分去下层的三乙胺盐酸盐水溶液。取上层酰氯-苯溶液与盐酸乙脒水溶液混合，搅拌，并于常温下缓缓滴加氢氧化钠溶液（摩尔配比为对氯苯酚：三氯硫磷：三乙胺：盐酸乙脒：氢氧化钠=1.0:0.5:1.0:0.6:1.2）。滴加完成后，在室温下反应1小时。随后，用65℃水洗涤并进行过滤，得到白色固体，干燥后即为毒鼠成品，并配制成含量为0.5%的毒饵。

合成制备方法

以对氯苯酚、三氯硫磷和盐酸乙脒等原料，按以下步骤合成：首先在缚酸剂（如三乙胺）作用下，一定量的三氯硫磷与计量的对氯苯酚反应生成中间体O,O-双(对氯苯基)硫代磷酰氯。以苯为溶剂，在室温条件下滴加对氯苯酚、三乙胺和苯混合液，并于滴加结束后搅拌反应15～30分钟。然后，加入水析出三乙胺盐酸盐并回收三乙胺，所得苯层为磷酰氯苯溶液。

再制备盐酸乙脒：在盐酸存在下，先将乙腈与乙醇作用，氨解脱去1分子乙醇得到盐酸乙脒。

接下来合成毒鼠磷：在反应釜中加入适量的盐酸乙脒和水搅拌溶解。同时滴加一定量的磷酰氯苯溶液和碱（摩尔配比为对氯苯酚：三氯硫磷：三乙胺：盐酸乙脒：氢氧化钠=1.0：0.5：1.0：0.6：1.2），并继续反应2小时。反应结束后，物料真空过滤，滤饼经水洗后于90℃干燥为原粉；滤液经蒸馏回收苯。

此外，上述生产过程也可采用相转移催化法合成，可省去无水条件及分离步骤，并减少昂贵的三乙胺作为缚酸剂使用。此方法已获中国专利(CN1051715B)。具体操作如下：在300L搪瓷釜中加入对氯苯酚（含403g/L）、三氯硫磷和苄基三乙基氯化铵溶于水中，搅拌冷却后滴加NaOH溶液，反应温度升至40～60℃并维持1～2小时。物料降至20℃后进行离心分离、水洗及干燥，最终收率为64%，纯度为87.4%。

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。
• [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。
• [EN] MOLECULES HAVING PESTICIDAL UTILITY, AND INTERMEDIATES, COMPOSITIONS, AND PROCESSES, RELATED THERETO<br/>[FR] MOLÉCULES PRÉSENTANT UNE UTILITÉ EN TANT QUE PESTICIDE, ET LEURS INTERMÉDIAIRES, COMPOSITIONS ET PROCÉDÉS
  申请人：DOW AGROSCIENCES LLC

  公开号：WO2017040194A1

  公开（公告）日：2017-03-09

  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 aga inst 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有用的分子领域，用于生产这种分子的过程，用于这种过程的中间体，含有这种分子的杀虫剂组合物，以及使用这种杀虫剂组合物对抗这些害虫的过程。这些杀虫剂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化学式（“化学式一”）的分子。