八甲磷 | 152-16-9

• 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: 八甲磷
• 中文别名: 殺丹；双(二甲胺基)磷酸酐；双磷酰胺；八甲基焦磷酰胺
• 英文名称: schradan
• 英文别名: octamethyl pyrophosphoramide；octamethyl-diphosphoric acid tetramide；octamethylpyrophosphoramide；octamethyldiphosphoramide；diphosphoric acid tetrakis-dimethylamide；Tetramethyl-diamidophosphorsaeure-anhydrid；N-[bis(dimethylamino)phosphoryloxy-(dimethylamino)phosphoryl]-N-methylmethanamine
• CAS: 152-16-9
• 化学式: C₈H₂₄N₄O₃P₂
• 分子量: 286.251
• InChiKey: SZKKRCSOSQAJDE-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  常温常压下稳定。 禁配物：强氧化剂、强酸。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  7

ADMET

代谢

植物、动物和昆虫对SCHRADAN的代谢降解产生了相同的...化合物。这个化合物经过异构化，随后失去甲醛并形成了庚甲基吡rophosphoramide。虽然形成N-氧化物是主要的途径，但也有一些磷酸的水解发生。

METABOLIC DEGRADATION OF SCHRADAN IN PLANTS, ANIMALS, & INSECTS GAVE RISE TO THE SAME ... CMPD. ... THIS UNDERWENT ISOMERIZATION WITH SUBSEQUENT LOSS OF FORMALDEHYDE & FORMATION OF HEPTAMETHYLPYROPHOSPHORAMIDE. ... WHILE FORMATION OF THE N-OXIDE IS THE PRIMARY PATHWAY, SOME HYDROLYSIS OF THE PHOSPHATE ALSO OCCURRED.

来源:Hazardous Substances Data Bank (HSDB)

代谢

雄性大鼠的新陈代谢速率比雌性大鼠更高。

... MALE /RATS/ METABOLIZE ... SCHRADAN ... AT A HIGHER RATE THAN FEMALE /RATS/.

来源:Hazardous Substances Data Bank (HSDB)

代谢

从SCHRADAN与大鼠肝脏孵化得到的初始代谢物以及通过多种化学试剂处理显示为N-氧化物。...用SCHRADAN处理的植物...已被证明能产生至少两种化合物，一种不稳定的一种更稳定的衍生物。...SCHRADAN被氧化为N-甲基醇衍生物，可能是通过过渡态N-氧化物的途径。第二，更稳定的组分来自...代谢被认为是由N-甲基醇衍生物进一步氧化产生的N-甲酰衍生物。...

THE INITIAL METABOLITE OBTAINED FROM SCHRADAN INCUBATION WITH RAT LIVER & BY VARIETY OF CHEM AGENTS WAS SHOWN TO BE N-OXIDE. ... PLANTS TREATED WITH SCHRADAN ... HAVE BEEN SHOWN TO PRODUCE AT LEAST TWO CMPD, AN UNSTABLE & A MORE STABLE DERIVATIVE. ... SCHRADAN IS OXIDIZED TO THE N-METHYLOL DERIV POSSIBLY BY WAY DERIVATIVE ... OF TRANSITORY N-OXIDE. SECOND, MORE STABLE COMPONENT FROM ... METABOLISM IS BELIEVED TO BE N-FORMYL DERIV PRODUCED BY FURTHER OXIDATION OF THE N-METHYLOL DERIVATIVE. ...

来源:Hazardous Substances Data Bank (HSDB)

代谢

理论计算表明，312天和1040天分别用于瓦伦西亚橙的50%和90%水解，而柠檬则分别需要16天和35天。实际处理后的值表明SCHRADAN逐渐分解，但不如理论所建议的那么迅速。

... /THEORETICAL/ CALCULATIONS INDICATED THAT 312 & 1040 DAYS ... REQUIRED FOR 50% & 90% HYDROLYSIS RESPECTIVELY, IN VALENCIA ORANGES, & 16 & 35 DAYS, RESPECTIVELY, IN LEMONS. VALUES OBTAINED AFTER ACTUAL TREATMENTS INDICATED A GRADUAL BREAKDOWN OF SCHRADAN BUT NOT AS RAPID AS THEORY SUGGESTS.

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）= 8 毫克/立方米/4小时

LCLo (rat) = 8 mg/m3/4h

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

毒理性

• 相互作用

管理员给予苯巴比妥钠和酚甘酸 @ 70 & 100 毫克/千克 IP，分别增加了 OMPA 的毒性。给予格鲁塞米、氯丙嗪盐酸盐和美普巴 @ 60、15 和 200 毫克/千克，也增加了 OMPA 的毒性。

ADMIN SODIUM PHENOBARBITAL & PHENAGLYCODOL @ 70 & 100 MG/KG IP, RESPECTIVELY, INCR TOXICITY OF OMPA MARKEDLY. ADMIN GLUTETHIMIDE, CHLORPROMAZINE HYDROCHLORIDE, & MEPROBAMATE @ 60, 15, & 200 MG/KG, RESPECTIVELY, ALSO INCR OMPA TOXICITY.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

一些吩噻嗪类药物可能拮抗，而另一些可能增强有机磷杀虫剂的毒性抗胆碱酯酶效果。/有机磷胆碱酯酶抑制剂/

Some phenothiazines may antagonize & some may potentiate the toxic anticholinesterase effects of ... /organophosphorus insecticides/. /Organophosphate cholinesterase inhibitors/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

在长期治疗中，肾上腺皮质激素对抗抗胆碱酯酶的抗青光眼作用（增加眼内压）。... 抗胆碱药对抗抗胆碱酯酶在自主神经和中央神经系统上的缩瞳（抗青光眼）和其他毒蕈碱作用。三环类抗抑郁药（抗胆碱能作用）对抗抗胆碱酯酶在青光眼中的抗青光眼（缩瞳）作用。... 具有抗胆碱能作用的抗组胺药对抗抗胆碱酯酶的缩瞳（抗青光眼）和中央神经系统作用。抗胆碱酯酶增强由抗组胺药引起的镇静和行为改变。抗胆碱酯酶药物在自主效应细胞上的作用，以及在某种程度上对中枢神经系统的作用，可被阿托品这种首选解毒剂所拮抗。巴比妥类药物的作用可被抗胆碱酯酶增强。... 二泛醇增强抗胆碱酯酶的效果。氟磷酸盐杀虫剂增强其他抗胆碱酯酶的效果。/抗胆碱酯酶/

In long term therapy, adrenocorticoids antagonize the antiglaucoma effects of anticholinesterases (incr ocular pressure). ... Anticholinergics antagonize the miotic (antiglaucoma) & other muscarinic effects of anticholinesterases on the autonomic & central nervous systems. Tricyclic antidepressants (anticholinergic effects) antagonize the antiglaucoma (miotic) effects of anticholinesterases in glaucoma. ... Antihistamines with anticholinergic effects antagonize the miotic (antiglaucoma) & CNS effects of anticholinesterases. Anticholinesterases potentiate tranquilizing & behavioral changes induced by antihistamines. The actions of anticholinesterase agents on autonomic effector cells, & to some extent those on CNS, are antagonized by atropine, an antidote of choice. Barbiturates are potentiated by anticholinesterases. ... Dexpanthenol potentiates the effects of anticholinesterases. Fluorophosphate insecticides potentiate the effects of other anticholinesterases. /Anticholinesterases/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在口服SCHRADAN后，一些药物以未改变的形式出现在尿液中，其中也含有来自杀虫剂的其他磷化合物。降解产物也存在于胆汁和粪便中。

AFTER AN ORAL DOSE OF SCHRADAN, SOME APPEARS UNCHANGED IN THE URINE, WHICH ALSO CONTAINS OTHER PHOSPHORUS COMPOUNDS DERIVED FROM THE INSECTICIDE. DEGRADATION PRODUCTS ARE ALSO PRESENT IN THE BILE AND FECES.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

经皮吸收SCHRADAN与大多数有机磷化合物相比相对较低。

PERCUTANEOUS ABSORPTION OF SCHRADAN IS RATHER LOW AS COMPARED WITH MOST ORGANOPHOSPHORUS COMPOUNDS. ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在植物的所有部位中，通过SAP进行转移。

TRANSLOCATED IN SAP TO ALL PARTS OF PLANTS.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

/SCHRADAN IS/RELATIVELY INERT AS DIRECT CONTACT INSECTICIDE BUT IS ABSORBED BY LEAVES & TRANSLOCATED RENDERING THE PLANT SYSTEMICALLY TOXIC TO MANY SAP-FEEDING INSECTS AND MITES. 施拉德安相对不活跃作为直接接触杀虫剂，但它能被叶子吸收并转移，使得植物对许多吸汁昆虫和螨类具有系统性毒性。

/SCHRADAN IS/ RELATIVELY INERT AS DIRECT CONTACT INSECTICIDE BUT IS ABSORBED BY LEAVES & TRANSLOCATED RENDERING THE PLANT SYSTEMICALLY TOXIC TO MANY SAP-FEEDING INSECTS AND MITES.

来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

制备方法

用作农药杀虫剂。

用途简介

暂无内容。

用途

用作农药杀虫剂。

反应信息

• 作为反应物：
  描述：

  八甲磷 在 potassium hydrogen bifluoride 、 苯 作用下， 生成 甲氟磷
  参考文献：
  名称：

  Schrader, 1947, # 714, p. 42

  摘要：

  DOI：
• 作为产物：
  描述：

  六甲基磷酰三胺 在 phosphorus pentoxide 作用下， 生成 八甲磷
  参考文献：
  名称：

  Principles of Phosphorus Chemistry. X. Reorganization of Polyphosphorus Compounds: the Phosphoryldimethylamides¹

  摘要：

  DOI：

  10.1021/ja01508a011

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。