灭蚁灵 | 2385-85-5

• 物质功能分类: 分析化学 - 标准品 - 化妆品标准品
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 灭蚁灵
• 中文别名: 十二氯五环[5.3.0.0(2,6).0(3,9).0(4,8)]癸烷；十二氯代八氢-亚甲基-环丁并[CD]戊搭烯；灭蚁乐；全氯五环癸烷
• 英文名称: mirex
• 英文别名: dodecachlorooctahydro-1,3,4-metheno-2H-cyclobuta[cd]pentalene；1,1a,2,2,3,3a,4,5,5,5a,5b,6-dodecachloro-octahydro-1,3,4-metheno-1H-cyclobuta(cd)pentalene；1,1a,2,2,3,3a,4,5,5,5a,5b,6-dodecachlorooctahydro-1,3,4-metheno-1H-cyclobuta[cd]pentalene；perchloropentacyclo[5.3.0.0(2,6).0(3,9).0(4,8)]decane；dechlorane；1,2,3,4,5,5,6,7,8,9,10,10-dodecachloropentacyclo[5.3.0.02,6.03,9.04,8]decane
• CAS: 2385-85-5
• 化学式: C₁₀Cl₁₂
• 分子量: 545.546
• InChiKey: GVYLCNUFSHDAAW-UHFFFAOYSA-N

物化性质

• 熔点：
  485℃
• 沸点：
  601.43°C (rough estimate)
• 密度：
  1.9086 (rough estimate)
• 闪点：
  2 °C
• 溶解度：
  可溶于氯仿（少许）
• 物理描述：
  Mirex is an odorless white crystalline solid. (USCG, 1999)
• 颜色/状态：
  Snow-white crystals from benzene
• 气味：
  Odorless
• 蒸汽密度：
  18.8 (NTP, 1992) (Relative to Air)
• 蒸汽压力：
  8X10-7 mm Hg at 25 °C
• 亨利常数：
  8.11e-04 atm-m3/mole
• 稳定性/保质期：
  避免让氧化物接触。
• 分解：
  Decomposes above 500 °C to give hexachlorobenzene; hexachloropentadiene was found in small amounts in the thermal residue; the products identified from vapor phase were carbon monoxide, carbon dioxide, hydrogen chloride, chlorine, carbon tetrachloride, & phosgene.
• 腐蚀性：
  Practically non-corrosive to metals
• 气味阈值：
  Odor low 5.0667 mg/cu m; Odor high 5.0667 mg/cu m.
• 保留指数：
  2470;2494;2512;2518;2472;2525.8;2504.6;2511.7;2470;2471.3

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

初步披露，mirex不会产生哺乳动物代谢物，这一信息已经通过大鼠长期喂养试验的完整报告得到证实。在雌性大鼠的脂肪中，mirex的浓度在每日给药停止约10个月后仅下降了40%。这使得这种多氯代化合物成为迄今为止遇到的最顽固的外源化合物之一。

Preliminary disclosure that mirex yields no mammalian metabolites has ... been confirmed by a full report of long-term feeding trials in rat. In fat of female rats, concentrations of mirex had declined by only 40% some 10 mo after cessation of daily dosing. This ranks this polychlorinated cmpd ... as one of most persistent xenobiotics yet encountered.

来源:Hazardous Substances Data Bank (HSDB)

代谢

Mirex不被人类或动物代谢...

Mirex is not metabolized by humans or animals ... .

来源:Hazardous Substances Data Bank (HSDB)

代谢

Mirex ... 是完全氯化的笼状分子...预计对酶的攻击相当抵抗...环境中的一个氯原子被还原取代，以产生光敏瑞克斯（8-单氢-瑞克斯），在大鼠中表现出类似瑞克斯的行为。还原脱氯可以在体内发生；2,8-二氢瑞克斯和5,10-二氢瑞克斯已被确认为大鼠代谢物。虽然2,8-二氢瑞克斯似乎没有进一步代谢，但5,10-二氢瑞克斯似乎被转化为更具极性的代谢物，这些代谢物出现在大鼠尿液中。

Mirex ... is the fully chlorinated cage molecule ... that might be expected to be rather resistant to enzymatic attack ... One chlorine atom is reductively replaced in the environment to give photomirex (8-monohydro-mirex), which appears to behave like mirex in the rat. Reductive dechlorination can occur in vivo; 2,8-dihydromirex and 5,10-dihydromirex have been identified as rat metabolites. Whereas 2,8-dihydromirex does no appear to be further metabolized, 5,10-dihydromirex appears to be converted into more polar metabolites, which appear in rat urine.

来源:Hazardous Substances Data Bank (HSDB)

代谢

Mirex很可能会被氧化成氯代酮。氯代酮的主要代谢物是氯代酮醇，它以葡萄糖醛酸苷的形式出现在人类胆汁中。

Mirex is probably oxidized to chlordecone. The main metabolite of chlordecone is chlordecone alcohol, which appears in human bile as glucuronic acid conjugates.

来源:Hazardous Substances Data Bank (HSDB)

代谢

米雷克斯主要通过消化道吸收，但也可能通过肺部和皮肤吸收。一旦被吸收，米雷克斯就会在体内广泛分布，但在脂肪组织中积累。它在体内的保留时间很长。米雷克斯在人体内不被代谢，并以原样在粪便中排出。

Mirex is mainly absorbed through the gastrointestional tract, but may also be absorbed through the lungs and skin. Once absorbed, mirex is widely distributed throughout the body but is sequestered in the adipose tissue. It has a long retention time in the body. Mirex is not metabolized by humans and is excreted unchanged in the feces. (L601)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

Mirex抑制钠/钾-转运ATP酶，产生神经毒性效应并损害能量依赖的细胞过程。

Mirex inhibits sodium/potassium-transporting ATPases, producing neurotoxic effects and impairing energy-dependent cellular processes. (A216)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌性证据

致癌性分类：1）人类证据：无数据；2）动物证据：充分。对人类致癌风险的总体评估为2B组：该物质可能对人类致癌。/来自表格/

Classification of carcinogenicity: 1) evidence in humans: no data; 2) evidence in animals: sufficient. Overall summary evaluation of carcinogenic risk to humans is Group 2B: The agent is possibly carcinogenic to humans. /From table/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

Mirex: 有合理预期为人类致癌物。

Mirex: reasonably anticipated to be a human carcinogen.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：灭蚁灵

IARC Carcinogenic Agent:Mirex

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：2B组：可能对人类致癌

IARC Carcinogenic Classes:Group 2B: Possibly carcinogenic to humans

来源:International Agency for Research on Cancer (IARC)

吸收、分配和排泄

米雷克斯通过胎盘转移到胎儿，并通过乳汁排出。

Mirex is transferred across the placenta to the fetus and is excreted with the milk.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

Mirex是一种亲脂性化合物，因此它在脂肪组织中的储存量要远远大于其他任何组织。对于以6毫克/千克体重的单次口服剂量给予Mirex的大鼠，组织和器官保留了大约34%的总剂量，其中28%在脂肪中，3.2%在肌肉中，0.09%在肾脏中，1.8%在肝脏中。

Mirex is a lipophilic compound and as such is stored in the adipose tissue to a much greater extent than in any other tissue. For rats /that/ were dosed with a single oral dose of mirex at 6 mg/kg body weight, the tissues and organs retained about 34% of the total dose, of which 28% was found in fat, 3.2% in muscle, 0.09% in the kidneys, and 1.8% in the liver.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在口服后，米雷克仅部分被身体吸收，其余部分，取决于给药剂量，以未改变的形式在粪便中排出。米雷克也可以通过吸入和皮肤接触被吸收。

Following oral ingestion, mirex is only partly absorbed into the body and the remainder, depending on the dose administered, is eliminated unchanged in the faeces. Mirex can also be absorbed following inhalation and via the skin.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

大约55%的单次口服剂量6毫克/千克体重的(14)C-灭鼠剂，给予大鼠后，在48小时内以未改变的形式从粪便中排出。当给予较低浓度的灭鼠剂（0.2毫克/千克体重）时，只有15%的给药灭鼠剂在48小时内排出。

Approximately 55% of a single oral dose of 6 mg (14)C-mirex/kg body weight, administered to rats, was excreted unchanged in the feces within 48 hr. When a lower concentration of mirex was administered (0.2 mg/kg body weight), only 15% of the administered mirex was excreted in 48 hr.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  Xn,F,Xi,N
• 安全说明：
  S13,S16,S26,S36,S36/37,S46,S60,S61
• 危险类别码：
  R21/22
• WGK Germany：
  3
• 危险品运输编号：
  2761
• RTECS号：
  PC8225000
• 海关编码：
  2903890030
• 包装等级：
  III
• 危险类别：
  6.1(b)
• 储存条件：
  请将容器密封，并将其存放在紧密封装的容器中，建议储存在阴凉、干燥的地方。

SDS

第一部分：化学品名称

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: 235 毫克/公斤
可燃性危险特性：受热分解产生有毒氯化物气体
储运特性：应存放在通风、低温和干燥的库房内，与食品原料分开储存和运输
灭火剂：砂土、干粉、泡沫

反应信息

• 作为反应物：
  描述：

  灭蚁灵 在 偶氮二异丁腈 、 三正丁基氢锡 氢氧化钾 、 RedAl 、 三乙二醇 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Dehalogenation of organic compounds-2: the metal catalyzed sodium borohydride or sodium alkoxyborohydride/tetraethylene glycol/koh dechlorination of mirex

  摘要：

  Polyethylene glycol (PEG) or tetraethylene glycol (TEG)/KOH when used in combination with either sodium borohydride or alkoxyborohydrides give very powerful reducing media which quantitatively destroy Mirex at about 70-degrees-C. The reduction rate is further increased by using the catalyst system, Bu3SnH/AlBN, where the disappearance of Mirex was complete within one hour at 58-degrees-C.

  DOI：

  10.1016/0040-4039(91)85069-h
• 作为产物：
  描述：

  六氯环戊二烯 在 三氯化铝 、 四氯乙烯 作用下， 生成 灭蚁灵
  参考文献：
  名称：

  Newcomer; McBee, Journal of the American Chemical Society, 1949, vol. 71, p. 952,954

  摘要：

  DOI：

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