1,2,3,4,10,10-六氯-6,7-环氧-1,4,4a,5,6,7,8,8a-八氢-1,4-内,内-5,8-二甲桥萘 | 128-10-9

• 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: 1,2,3,4,10,10-六氯-6,7-环氧-1,4,4a,5,6,7,8,8a-八氢-1,4-内,内-5,8-二甲桥萘
• 中文别名: 3,4,5,6,9,9-六氯-1a,2,2a,3,6,6a,7,7a-八氢-2,7:3,6-二亚甲基萘并[2,3-b]恶丙烯
• 英文名称: dieldrin
• 英文别名: endrin；1,2,3,4,10,10-Hexachlor-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-1,4,5,8-dimethano-naphthalin；3,4,5,6,13,13-hexachloro-10-oxapentacyclo[6.3.1.13,6.02,7.09,11]tridec-4-ene
• CAS: 128-10-9
• 化学式: C₁₂H₈Cl₆O
• 分子量: 380.913
• InChiKey: DFBKLUNHFCTMDC-UHFFFAOYSA-N

物化性质

• 物理描述：
  Dieldrin is a light-tan flaked solid. It is insoluble in water. It is toxic by inhalation, skin absorption and ingestion. It can penetrate intact skin. It is used as an insecticide.
• 颜色/状态：
  WHITE, CRYSTALLINE SOLID
• 气味：
  Odorless
• 沸点：
  330.0 °C
• 熔点：
  201.75 °C
• 闪点：
  80°F (commercial product may contain flammable liquid)
• 溶解度：
  Solubility in g/100 ml solvent at 25 °C: acetone 17, benzene 13.8, carbon tetrachloride 3.3, hexane 7.1, and xylene 18.3
• 密度：
  Specific gravity 1.7 @ 20 °C.
• 蒸汽密度：
  13.2 (NTP, 1992) (Relative to Air)
• 蒸汽压力：
  3X10-6 mm Hg @ 20 °C
• 亨利常数：
  8.18e-06 atm-m3/mole
• 稳定性/保质期：

  Endrin is stable in the presence of most alkalis but rearranges to delta-keto endrin in the presence of strong acids, in sunlight and when heated.

• 分解：
  Decomposes above 200 °C.
• 腐蚀性：
  Slightly corrosive to metals
• 气味阈值：
  1.80x10-2 ppm (perfume/flavor grade purity).
• 保留指数：
  2150.8

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

在动物体内，恩德林被降解，主要是转化为9-酮恩德林和9-羟基恩德林，但也转化为5-羟基恩德林。

IN ANIMALS, ENDRIN IS DEGRADED, LARGELY TO 9-KETOENDRIN & 9-HYDROXYENDRIN, BUT ALSO TO 5-HYDROXYENDRIN.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在6天的时间段内，雄性/大鼠/服用豆油中的恩德林，通过粪便排出了66%的剂量...雌性...37%。...对粪便的分析/显示/恩德林...抗-12-羟基恩德林...合成-12-羟基恩德林...3-羟基恩德林...12-酮恩德林...和德尔塔-酮恩德林...。

IN A 6-DAY PERIOD, MALES /RATS ADMIN ENDRIN IN ARACHIS OIL/ EXCRETED IN FECES 66% DOSE ... FEMALES ... 37%. ... ANALYSIS /FECES/ REVEALED ... ENDRIN ... ANTI-12-HYDROXYENDRIN ... SYN-12-HYDROXYENDRIN ... 3-HYDROXYENDRIN ... 12-KETOENDRIN ... & DELTA-KETOENDRIN ... .

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠中给予恩德林后，对粪便的分析揭示了一种极性代谢物...反式-4,5-二氢异恩德林-4,5-二醇。另一种极性的...尚未鉴定。...雄性大鼠的尿液中含恩德林，12-酮恩德林，反-12-羟基恩德林和3-羟基恩德林（比例分别为17:19:2:1）。雌性大鼠的提取物中不含12-酮恩德林。/建议：12-酮恩德林是最有毒的/。

/IN RATS ADMIN ENDRIN, ANALYSIS OF FECES REVEALED/ A POLAR METABOLITE ... TRANS-4,5-DIHYDROISODRIN-4,5-DIOL. ANOTHER POLAR ... NOT IDENTIFIED. ... URINE FROM MALE RATS CONTAINED ENDRIN, 12-KETOENDRIN, ANTI-12-HYDROXYENDRIN & 3-HYDROXYENDRIN (17:19:2:1, RESPECTIVELY). THE EXTRACTS FROM FEMALE RATS DID NOT CONTAIN 12-KETOENDRIN. /SRP: 12-KETOENDRIN IS THE MOST TOXIC/.

来源:Hazardous Substances Data Bank (HSDB)

代谢

/ENDRIN ADMIN TO RATS IN 6 DAY STUDY/ ... MAJOR METABOLITE IN FEMALE RAT URINE /WAS/ IDENTICAL TO 12-HYDROXYENDRIN O-SULFATE. IN TISSUES /ANALYZED/ 12-KETOENDRIN /WAS/ MAJOR CMPD IN FAT OF MALES; ENDRIN IN FEMALES /BUT/ 12-KETOENDRIN WAS ALSO PRESENT. IN LIVER OF MALES NO ENDRIN /WAS DETECTED/ & 12-KETOENDRIN /WAS/ MAJOR METABOLITE. 六天研究中给大鼠内服恩德林...雌鼠尿中的主要代谢物与12-羟基恩德林O-硫酸盐相同。在分析的组织中，12-酮恩德林是雄性脂肪中的主要化合物；雌性中是恩德林，但12-酮恩德林也存在。在雄性肝脏中没有检测到恩德林，而12-酮恩德林是主要的代谢物。

/ENDRIN ADMIN TO RATS IN 6 DAY STUDY/ ... MAJOR METABOLITE IN FEMALE RAT URINE /WAS/ IDENTICAL TO 12-HYDROXYENDRIN O-SULFATE. IN TISSUES /ANALYZED/ 12-KETOENDRIN /WAS/ MAJOR CMPD IN FAT OF MALES; ENDRIN IN FEMALES /BUT/ 12-KETOENDRIN WAS ALSO PRESENT. IN LIVER OF MALES NO ENDRIN /WAS DETECTED/ & 12-KETOENDRIN /WAS/ MAJOR METABOLITE.

来源:Hazardous Substances Data Bank (HSDB)

代谢

环戊二烯杀虫剂主要经口吸收，并主要分布到脂肪和皮肤中。其主要生物转化产物是对映-2-羟基环戊二烯和相应的硫酸盐，以及葡萄糖苷酸代谢物。对映-和同分-12-羟基环戊二烯以及12-酮环戊二烯是环戊二烯的主要有毒代谢物。环戊二烯及其代谢物通过尿液和粪便排出体外。(L112)

Endrin 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. Endrin 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

艾氏剂拮抗神经递质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。艾氏剂还抑制了Na+ K+ ATP酶和Ca2+和Mg2+ ATP酶，这些酶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，随后邻近神经元的去极化，以及刺激在中枢神经系统中的传播。艾氏剂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。

Endrin 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. Endrin 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. Endrin 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

• 致癌性证据

癌症分类：D组 不可归类为人类致癌性

Cancer Classification: Group D Not Classifiable as to Human Carcinogenicity

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

分类：D；无法归类为人类致癌性。分类依据：对两种品系的小鼠进行口服毒死蜱处理，在雌雄两性中均未产生致癌作用。国家癌症研究所（NCI）的生物鉴定显示雄性和雌性大鼠有反应，尽管NCI报告了无证据结论。几个生物鉴定的不充分性使得报告的阴性结果的可信度受到质疑。这些不充分性和NCI生物鉴定中的提示性反应不支持E组的分类；而是D组的分类最能反映这些不确定的数据。人类致癌性数据：不充分。动物致癌性数据：不充分。

CLASSIFICATION: D; not classifiable as to human carcinogenicity. BASIS FOR CLASSIFICATION: Oral administration of endrin did not produce carcinogenic effects in either sex of two strains of mice. An NCI bioassay was suggestive of responses in male and female rats although NCI reported a no evidence conclusion. The inadequacies of the several bioassays call into question the strength of the reported negative findings. These inadequacies and the suggestive responses in the NCI bioassay do not support a Group E classification; rather a Group D classification best reflects the equivocal data. HUMAN CARCINOGENICITY DATA: Inadequate. ANIMAL CARCINOGENICITY DATA: Inadequate.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

没有关于人类的数据。动物致癌性证据不足。总体评估：第3组：该物质对人类致癌性无法分类。

No data are available in humans. Inadequate evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A4：不能分类为人类致癌物。

A4: Not classifiable as a human carcinogen.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

恩德林从血浆中清除的速度比狄尔德林快得多，这是因为恩德林有更快的胆汁排泄。

... ENDRIN IS CLEARED MUCH MORE RAPIDLY FROM PLASMA THAN DIELDRIN BECAUSE OF MORE RAPID BILIARY EXCRETION.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在棉花植物的叶面上涂抹了(14)C-恩德林之后十二周，33%的放射性物质被回收，其中26%在叶子和叶子内部，其余在植物的其他部分和土壤中。

TWELVE WK AFTER APPLICATION OF (14)C ENDRIN TO UPPER LEAF SURFACES OF COTTON PLANTS, 33% OF THE APPLIED RADIOACTIVITY WAS RECOVERED, 26% ON & IN THE LEAVES & THE REMAINDER IN THE OTHER PLANT PARTS & SOIL.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

恩德林在牛的体脂中积累，并且以小量排泄在它们的牛奶中。

ENDRIN IS ACCUM IN THE BODY FAT OF COWS & IS EXCRETED IN SMALL AMT IN THEIR MILK.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

与其他有机氯杀虫剂相比，VERY LITTLE ENDRIN在动物体内的储存非常少。

VERY LITTLE ENDRIN, AS COMPARED TO OTHER ORGANOCHLORINE INSECTICIDES, IS STORED IN ANIMALS.

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。
• TETRAZOLINONE COMPOUND AND USE OF SAME
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20160081339A1

  公开（公告）日：2016-03-24

  A tetrazolinone compound of formula (1): wherein R 1 and R 2 each independently represents a hydrogen atom, etc.; R 3 represents a C1-C6 alkyl group, etc.; R 4 , R 5 , and R 6 each independently represents a hydrogen atom, etc.; A represents a C6-C16 aryl group optionally having one or more atoms or groups selected from Group P, etc.; Q represents the following group Q1, etc.; and X represents an oxygen atom or a sulfur atom, has excellent control activity against pests.

  一种化学式（1）所示的四唑酮化合物： 其中R1和R2分别独立表示氢原子，等等； R3表示C1-C6烷基，等等；R4、R5和R6分别独立表示氢原子，等等；A表示一个C6-C16芳基，可选地具有来自P族等组的一个或多个原子或基团；Q表示以下Q1组等；以及 X表示氧原子或硫原子，对害虫具有出色的控制活性。
• [EN] BENZOTHIAZOLE CARBOXAMIDES AS FUNGICIDES<br/>[FR] BENZOTHIAZOLE CARBOXAMIDES EN TANT QUE FONGICIDES
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2009157527A1

  公开（公告）日：2009-12-30

  An amide compound of the formula (I): (wherein, R1 represents a hydrogen atom or fluorine atom and R2 represents a C1 to C6 linear alkyl group or linear (C1-C2 alkoxy)C2-C5 alkyl group.) has an excellent controlling effect on a plant disease.

  化合物的结构式（I）如下：（其中，R1代表氢原子或氟原子，R2代表C1到C6的直链烷基或直链（C1-C2烷氧基）C2-C5烷基。）对植物病害有出色的控制效果。