碳氯灵 | 297-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 中文名称: 碳氯灵
• 中文别名: 八氯六氢亚甲基苯并呋喃；1,3,4,5,6,7,8,8-1八氯,3,3a,4,7,7a,-六氯-4,7-甲撑-异苯并呋喃；1,3,4,5,6,7,8,8-八氯-1,3,3a,4,7,7a-六氢-4,7-甲撑异苯并呋喃；1,2,3,4,5,6,7,8,8-八氯-3A,4,7,7A四氢-4,7-亚甲桥苯并呋喃
• 英文名称: telodrin
• 英文别名: isobenzan；1,3,4,5,6,7,10,10-Octachlor-4,7-endomethylen-4,7,8,9-tetrahydrophthalan-<¹⁴C>；1,3,4,5,6,7,10,10-Octachlor-4,7-methylen-4,7,8,9-tetrahydrophthalan；1,3,4,5,6,7,10,10-Octachlor-4,7-methano-4,7,8,9-tetrahydrophthalan；¹⁴C-Telodrin；1,3,5,7,8,9,10,10-octachloro-4-oxatricyclo[5.2.1.02,6]dec-8-ene
• CAS: 297-78-9
• 化学式: C₉H₄Cl₈O
• 分子量: 411.754
• InChiKey: LRWHHSXTGZSMSN-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  受热会释放出有毒的氯化物气体。

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

在含有微生物的介质中，异苯并芘的浓度较低时，会转化为极性代谢物A（可能是轭合物）的比例可达99%。A在用盐酸水解后，会得到一个极性较低的未知结构的产物。蚊幼虫将异苯并芘转化为三种高度极性的产物。其中两种用盐酸水解后，色谱行为没有变化；然而第三种水解后得到的产物在各方面都与内酯相同...。

At low concn of isobenzan in medium containing the microorganism conversion to a polar metabolite A (presumably a conjugate) occurred up to 99%. A, upon hydrolysis with hydrochloric acid, gave a less polar product of unknown structure. Mosquito larvae converted isobenzan to three highly polar products. Hydrolysis of two of these with hydrochloric acid did not change their chromatographic behavior; the third, however, gave a product that in all respects was identical to the lactone ... .

来源:Hazardous Substances Data Bank (HSDB)

代谢

静脉注射后，雄性和雌性大鼠在48小时内分别以亲水性代谢物的形式排出了13%和16%的放射性异苯腈。

Following iv injection, 13 and 16% of radioactive isobenzan was excreted /in urine/ in 48 hr by male and female rats, respectively, in the form of a hydrophillic metabolite.

来源:Hazardous Substances Data Bank (HSDB)

代谢

亲水性代谢物形成，其中一种已被确认为异苯并环庚三烯内酯。...蚊子幼虫和土壤真菌以与脊椎动物相同的方式代谢异苯并环庚三烯，产生异苯并环庚三烯内酯作为代谢物。

Hydrophilic metabolites are formed, one of which has been identified as isobenzan lactone. ...Mosquito larvae and soil fungi metabolize isobenzan in the same way as vertebrates, yielding isobenzan lactone as a metabolite.

来源:Hazardous Substances Data Bank (HSDB)

代谢

它通过口服吸收并主要分布到脂肪和皮肤。主要的生物转化产物是对映体2-羟基艾氏剂和相应的硫酸盐，以及葡萄糖苷酸代谢物。对映体和同分异构体12-羟基艾氏剂及12-酮艾氏剂是艾氏剂的主要有毒代谢物。艾氏剂及其代谢物通过尿液和粪便排出体外。

It is absorbed orally and distributed primarily to the fat and skin. The major biotransformation product is anti-l 2-hydroxyendrin and the corresponding sulfate, as well as glucuronide metabolites. Anti- and syn-12-hydroxyendrin and 12-ketoendrin are the main toxic metabolites of endrin. It and its metabolites are excreted in urine and feces. (L112)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

它拮抗了神经递质γ-氨基丁酸（GABA）在GABA-A受体上的作用，有效地阻断了GABA诱导的氯离子摄取，导致中枢神经系统的过度兴奋性。它还抑制了Na+ K+ ATPase和Ca2+和Mg2+ ATPase，这对于钙离子跨膜转运至关重要。这导致细胞内游离钙离子的积累，促进储存囊泡中神经递质的释放，随后相邻神经元的去极化，以及刺激在中枢神经系统中的传播。它还导致肝细胞中脂质过氧化增加、膜流动性降低和DNA损伤，但确切机制尚不清楚。（T10，L112）

It antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. It also inhibits Na+ K+ ATPase and Ca2+ and Mg2+ ATPase which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. It also causes increased lipid peroxidation, decreased membrane fluidity, and DNA damage in hepatocytes, but the exact mechanism is unknown. (T10, L112)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

无致癌性迹象（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity (not listed by IARC). (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

中毒主要影响神经系统。暴露会导致各种有害影响，包括过度兴奋、严重的中枢神经系统损伤和死亡。还认为它会导致出生缺陷。(T10, L112)

Poisoning affects primarily the nerve system. Exposure causes various harmful effects including hyperexcitability, severe central nervous system damage, and death. It is also believed to cause birth defects. (T10, L112)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口腔 (L111)

Oral (L111)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

可能由狄氏剂中毒引起的症状包括头痛、眩晕、紧张、混乱、恶心、呕吐和抽搐。

Symptoms that may result from endrin poisoning are headaches, dizziness, nervousness, confusion, nausea, vomiting, and convulsions. (L112)

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

异恶苯是可以通过皮肤、呼吸系统和胃肠道被吸收的……在给雄性和雌性大鼠静脉注射后48小时内，分别有13%和16%的放射性异恶苯以亲水性代谢物的形式被排泄。

Isobenzan is absorbed by the skin as well as by the respiratory and GI tracts. ... Following iv injection, 13 and 16% of radioactive isobenzan was excreted in 48 hr by male and female rats, respectively, in the form of a hydrophillic metabolite.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

(14)C标记的杀虫剂...在不同组织、血液、尿液和粪便中的命运在大鼠和家兔中进行了追踪，雄性和雌性大鼠以及雄性家兔通过静脉注射杀虫剂。在大鼠中，在给药后48小时对杀虫剂进行了评估...在兔子中，在144小时后进行了评估。大鼠以15微克/公斤的剂量接受杀虫剂...家兔以241微克/公斤的剂量接受...杀虫剂。在48小时内，雄性大鼠排泄了13%的杀虫剂放射性，雌性大鼠排泄了16%。在96小时内，家兔排泄了13%的杀虫剂放射性，主要是以亲水性代谢物的形式。与这个组中的其他杀虫剂相比，雌性大鼠在大多数分析的组织中储存了明显较少的杀虫剂...血液、肝脏、生殖腺、肾脏、肠道、脾脏、胃、心脏、肺、大脑、腹部和皮下脂肪、肌肉和全身。相应地，雌性大鼠在尿液和粪便中排泄的化合物比雄性多。与埃及伊蚊幼虫一样，杀虫剂产生了一种代谢物，在水解过程中产生了内酯。...

The fate of (14)C-labeled telodrin... was followed in various tissues, blood, urine and feces of both male and female rats and in male rabbits dosed iv with insecticides. In rats telodrin was evaluated 48 hr after dosing... and in rabbits after 144 hr. Rats received telodrin at 15 ug/kg... . Rabbits received... telodrin at 241 ug/kg. Male rats excreted 13% of the telodrin radioactivity and female rats, 16% in 48 hr. Within 96 hr, rabbits excreted 13% of the telodrin radioactivity, chiefly as a hydrophilic metabolite. ...In contrast to other insecticides of this group, female rats stored markedly less telodrin... in most of the tissues analyzed, blood, liver, gonads, kidneys, gut, spleen, stomach, heart, lung, brain, abdominal and subcutaneous fat, muscle and whole body. Correspondingly, female rats excreted more of the compounds than did males in the urine and feces. As in Aedes aegypti larvae, telodrin gave a metabolite which, in hydrolysis, yielded a lactone. ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

异恶苯是很容易通过胃肠壁被吸收的，并且以未改变的化合物形式在血液中运输。会形成亲水性代谢物，其中一种已被确认为异恶苯内酯。异恶苯在大鼠和狗的组织和器官中按以下顺序积累：脂肪>肝脏=肌肉>大脑>血液。雌性大鼠的组织浓度通常高于雄性，特别是在体脂肪中。在大鼠体脂肪中发现的生物半衰期是10.9天（雄性大鼠）和16.6天（雌性大鼠）。

Isobenzan is readily absorbed through the gastrointestinal wall and is transported in the blood as the unchanged compound. Hydrophilic metabolites are formed, one of which has been identified as isobenzan lactone. Isobenzan accumulates in the tissues and organs of rats and dogs in the following order: fat >liver =muscle >brain >blood. The tissue concentrations of female rats are generally higher than those of males, especially in body fat. The biological half-life in body fat was found to be 10.9 days in male rats and 16.6 days in female rats.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

异苯肼在大鼠和兔子的血液中运输时，会与一些血清蛋白（兔子的白蛋白和α-球蛋白，大鼠的白蛋白）以及红细胞成分，主要是血红蛋白结合。杀虫剂在血浆和细胞之间分布的比例大约为2:1，这一比例在给药后不同时间间隔和不同浓度下保持恒定。气相色谱显示，未改变的异苯肼在血液中运输。

Isobenzan is approximately 4000 times more soluble in rabbit serum than in water, and it has been shown that, during transport in the blood of rats and rabbits, isobenzan is associated with some serum proteins (albumin and alpha-globulin in the rabbit and albumins in the rat) and with constituents of the red blood cell, mainly hemoglobin. The ratio of the distribution of the insecticide between plasma and cells was shown to be approximately 2:1, this ratio remaining constant at different intervals after administration and at different concentrations. Gas chromatography showed that unchanged isobenzan was transported in the blood.

来源:Hazardous Substances Data Bank (HSDB)

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。

表征谱图