吗啉,4-[(2E)-3-(4-氯苯基)-3-(3,4-二甲氧苯基)-1-羰基-2-丙烯基]- | 113210-97-2

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 吗啉,4-[(2E)-3-(4-氯苯基)-3-(3,4-二甲氧苯基)-1-羰基-2-丙烯基]-
• 英文名称: dimethomorph
• 英文别名: E-dimethomorph；(E)-4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloyl]morpholine；(E)-dimethomorph；3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-morpholin-4-yl-propenone；3-(4 chlorophenyl)-3-(3,4-dimethoxyphenyl) acrylic acid morpholide；3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl) acrylic acid morpholide；(E)-3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-morpholin-4-ylprop-2-en-1-one
• CAS: 113210-97-2
• 化学式: C₂₁H₂₂ClNO₄
• 分子量: 387.863
• InChiKey: QNBTYORWCCMPQP-NBVRZTHBSA-N

物化性质

• 沸点：
  584.9±50.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)
• 颜色/状态：
  Colorless to grey crystalline powder
• 气味：
  Odorless
• 熔点：
  148.0 °C
• 溶解度：
  In water (mg/L at 20 °C): 81.1 at pH 4; 49.2 at pH 7; 41.8 at pH 9
• 蒸汽压力：
  7.39X10-6 mm Hg at 25 °C
• 稳定性/保质期：

  Hydrolytically and thermally stable under normal conditions. Stable for >5 years in the dark. The (E)- and (Z)-isomers are interconverted in sunlight.

• 碰撞截面：
  199.03 Ų [M+H]+ [CCS Type: TW]
• 保留指数：
  3159.3

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

代谢

大鼠口服二甲基吗啡（10毫克/千克单次剂量；10毫克/千克14天重复剂量；10毫克/千克7天重复剂量；500毫克/千克单次剂量）导致大鼠尿液和粪便中迅速排泄。尿液中的代谢物是由二甲基氧苯环脱甲基和吗啡环氧化产生的。低剂量治疗后的胆汁代谢物占粪便排泄的大部分。主要的胆汁代谢物是通过对二甲基氧苯环脱甲基产生的化合物中的一种或两种化合物的葡萄糖苷酸化产生的。报告提供了二甲基吗啡的代谢途径。

Rat Oral administration of dimethomorph (10 mg/kg single dose; 10 mg/kg 14-day repeated dose; 10 mg/kg 7-day repeated dose; 500 mg/kg single dose) results in rapid excretion into the urine and feces of rats. ... Urinary metabolites resulted from demethylation of the dimethoxyphenyl ring and oxidation of the morpholine ring. ...Biliary metabolites accounted for most of the fecal excretion following low-dose treatment. The major biliary metabolites were glucuronides of one and possibly two of the compounds produced by demethylation of the dimethoxyphenyl ring. The report provided a proposed metabolic pathway for dimethomorph.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠中，主要的代谢途径是去甲基化其中一个二甲氧基团，或者是氧化吗啡啉环上CH2基团（邻位或间位）之一。

In rats, the major route of metabolism is demethylation of one of the dimethoxy groups or by oxidation of one of the CH2 groups (ortho- or meta-position) of the morpholine ring.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

癌症分类：不太可能对人类致癌

Cancer Classification: Not Likely to be Carcinogenic to Humans

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

据报道，广泛使用的杀虫剂的混合物可以产生超出最有效单一成分引起的反应的联合AR拮抗作用，并且这种作用是可以预测的。

... /It was reported/ that a mixture of widely used pesticides can produce combined AR antagonist effects that exceed the responses elicited by the most potent component alone in a predictable manner.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中毒物清除。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或置于左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，辅助通气。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，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……。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，则用温水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. 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 0.9% saline (NS) 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注D5W /SRP: "保持开放"，最小流量/。如果出现低血容量的迹象，使用0.9%的生理盐水（NS）或乳酸林格氏液。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……。使用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。 /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

大鼠口服二甲基恶霉灵（单次剂量10 mg/kg；14天重复剂量10 mg/kg；7天重复剂量10 mg/kg；单次剂量500 mg/kg）会导致该物质在大鼠的尿液和粪便中迅速排出。在所有治疗协议中，大部分（80-90%）给予的放射性标记物通过粪便排出。通过尿液排出的量相对较少（6-16%），而在器官和组织中检测到的水平非常低（0.1-0.4%）。通过尿液和胆汁中代谢物的迅速排出可以推断出物质的快速吸收。单次高剂量（500 mg/kg）后吸收的饱和度通过粪便中大量（50%）的放射性活性与母体化合物相关联来表明。对于低剂量或高剂量治疗，雌性大鼠的尿液排出量往往比雄性大鼠更高（在低剂量大鼠中可高达2倍）。二甲基恶霉灵或（14）C-二甲基恶霉灵派生的放射性活性的保留在大多数组织中通常为1%，尽管肝脏显示出略高的水平（1.4%），而胃肠器官中的较高水平是由于腔内容物中的放射性活性。

Rat Oral administration of dimethomorph (10 mg/kg single dose; 10 mg/kg 14-day repeated dose; 10 mg/kg 7-day repeated dose; 500 mg/kg single dose) results in rapid excretion into the urine and feces of rats. For all treatment protocols, most (80-90%) of the radiolabel administered was excreted in the feces. A considerably smaller amount (6-16%) was excreted in the urine and only minimal levels (0.1-0.4%) were detected in the organs and tissues. Rapid absorption may be inferred by the rapid excretion of metabolites in the urine and bile. Saturation of absorption following single high doses (500 mg/kg) was indicated by large amounts (50%) of radioactivity in the feces being associated with parent compound. For low- or highdose treatment, urinary excretion in female rats tended to be greater (up to 2-fold in low-dose rats) than that of male rats. Retention of dimethomorph or (14)C-dimethomorph-derived radioactivity was generally 1% for most tissues although the liver exhibited slightly higher levels (1.4%) and higher levels in the gastrointestinal tract organs were due to radioactivity in the lumenal contents.

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为产物：
  描述：

  3-(4-chlorophenyl)-1-morpholinoprop-2-yn-1-one 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 吗啉,4-[(2E)-3-(4-氯苯基)-3-(3,4-二甲氧苯基)-1-羰基-2-丙烯基]-
  参考文献：
  名称：

  协同钯/路易斯酸催化的炔酸酯区域和立体发散双硅烷化：范围、机制和选择性起源

  摘要：

  介绍了使用乙硅烷试剂 TMDQ 进行的 Pd 催化的炔酸酯发散双硅烷基化反应（参见 TOC 图）。通过添加路易斯酸获得了反向区域选择性和立体选择性。MAD（甲基铝双（2,6-二叔丁基-4-甲基苯酚））通过空间效应影响电子有利的迁移插入，而添加 BCF（三（五氟苯基）硼烷）允许还原消除作为速率决定步骤。

  DOI：

  10.1002/anie.202309169

文献信息

• [EN] ACC INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE L'ACC ET UTILISATIONS ASSOCIÉES
  申请人：GILEAD APOLLO LLC

  公开号：WO2017075056A1

  公开（公告）日：2017-05-04

  The present invention provides compounds I and II useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.

  本发明提供了化合物I和II，这些化合物可用作乙酰辅酶A羧化酶（ACC）的抑制剂，以及它们的组合物和使用方法。
• [EN] BICYCLYL-SUBSTITUTED ISOTHIAZOLINE COMPOUNDS<br/>[FR] COMPOSÉS ISOTHIAZOLINE SUBSTITUÉS PAR UN BICYCLYLE
  申请人：BASF SE

  公开号：WO2014206910A1

  公开（公告）日：2014-12-31

  The present invention relates to bicyclyl-substituted isothiazoline compounds of formula (I) wherein the variables are as defined in the claims and description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

  本发明涉及公式（I）中变量如索权和说明中所定义的自行车基取代异噻唑啉化合物。这些化合物对抗或控制无脊椎动物害虫，特别是节肢动物害虫和线虫方面具有用途。该发明还涉及一种通过使用这些化合物来控制无脊椎动物害虫的方法，以及包含所述化合物的植物繁殖材料、农业和兽医组合物。
• [EN] AZOLINE COMPOUNDS<br/>[FR] COMPOSÉS AZOLINE
  申请人：BASF SE

  公开号：WO2015128358A1

  公开（公告）日：2015-09-03

  The present invention relates to azoline compounds of formula (I) wherein A, B1, B2, B3, G1, G2, X1, R1, R3a, R3b, Rg1 and Rg2 are as defined in the claims and the description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

  本发明涉及式（I）的噁唑啉化合物，其中A、B1、B2、B3、G1、G2、X1、R1、R3a、R3b、Rg1和Rg2如权利要求和描述中所定义。这些化合物对抗或控制无脊椎动物害虫，特别是节肢动物害虫和线虫方面具有用途。该发明还涉及一种利用这些化合物控制无脊椎动物害虫的方法，以及包括所述化合物的植物繁殖材料、农业和兽医组合物。
• [EN] SUBSTITUTED QUINAZOLINES AS FUNGICIDES<br/>[FR] QUINAZOLINES SUBSTITUÉES, UTILISÉES EN TANT QUE FONGICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2010136475A1

  公开（公告）日：2010-12-02

  The present invention relates to a compound of formula (I) wherein wherein the substituents have the definitions as defined in claim 1or a salt or a N-oxide thereof, their use and methods for the control and/or prevention of microbial infection, particularly fungal infection, in plants and to processes for the preparation of these compounds.

  本发明涉及一种具有如下式（I）的化合物，其中取代基具有权利要求1中定义的定义，或其盐或N-氧化物，它们的用途以及用于控制和/或预防植物中微生物感染，特别是真菌感染的方法，以及制备这些化合物的方法。
• [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。