四氯硝基苯 | 117-18-0

• 物质功能分类: 化学农药原药 - 杀菌剂 - 其他杀菌剂
• 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: 四氯硝基苯
• 英文名称: 2,3,5,6-Tetrachloronitrobenzene
• 英文别名: Tecnazene；1,2,4,5-tetrachloro-3-nitrobenzene
• CAS: 117-18-0；28804-67-3
• 化学式: C₆HCl₄NO₂
• mdl: MFCD00007066
• 分子量: 260.891
• InChiKey: XQTLDIFVVHJORV-UHFFFAOYSA-N

物化性质

• 熔点：
  98-101 °C(lit.)
• 沸点：
  304 °C(lit.)
• 密度：
  1.744 g/cm3 (25 ºC)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 物理描述：
  2,3,5,6-tetrachloronitrobenzene appears as pale yellow crystals. (NTP, 1992)
• 颜色/状态：
  Colorless crystals
• 气味：
  ODORLESS
• 蒸汽压力：
  0.0018 mm Hg at 15 °C (est)
• 稳定性/保质期：
  Very stable to acids and bases. Stable to heat up to almost 300 °C.
• 分解：
  In solution, decomposes slowly when exposed to UV radiation.
• 腐蚀性：
  Non corrosive at room temp
• 保留指数：
  1607.4;1567.7;1565.1;1585.1

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

[U-14C]-2,3,5,6-四氯硝基苯（特克纳泽）在雄性和雌性大鼠单次给药1 mg/kg后的代谢命运已经确定，以及在手术准备、胆管插管的雄性大鼠单次口服给药135 mg/kg后的代谢命运。在雌性大鼠中，放射性物质主要随尿液排出（82%）。然而，雄性大鼠在大鼠的尿液和粪便中大约等量排出放射性物质（后者通过胆汁）。主要代谢途径是与谷胱甘肽（GSH）结合并伴随硝基位移。GSH结合物和相关代谢物随胆汁排出，最终以巯基尿酸结合物的形式随尿液排出。半胱氨酸结合物经过β-裂解酶介导的代谢，产生一个硫醇，随后发生甲基化生成硫代苯甲醚，然后发生S-氧化。还形成了一种新型的四氯甲基硫化物代谢物。

The metabolic fate of [U-14C]-2,3,5,6-tetrachloronitrobenzene (tecnazene) has been determined in the male and female rat following a single dose of 1 mg/kg and in surgically prepared, bile-duct-cannulated rats following a single oral dose of 135 mg/kg. Radioactivity in the female rat was excreted mainly in urine (82%). The male rat, however, excreted approximately equal amounts of radioactivity in urine and feces (the latter via bile). The principal metabolic pathway was conjugation with glutathione (GSH) and concomitant nitro-displacement. The GSH-conjugate and related metabolites were excreted in the bile and ultimately in the urine as the mercapturic acid conjugate. The cysteine conjugate underwent beta-lyase-mediated metabolism to yield a thiol that underwent subsequent methylation to the thioanisole followed by S-oxidation. 4. A novel tetrachloromethyldisulphide metabolite was also formed.

来源:Hazardous Substances Data Bank (HSDB)

代谢

一些硝基团在给兔子口服2,3,5,6-四氯硝基苯后在小肠中发生了还原反应。极微量的四氯苯胺、巯基尿酸、自由的4-氨基-2,3,5,6-四氯酚、硫酸盐和葡萄糖苷酸在尿液中排出。

Some redn of nitro group took place in gut after admin of 2,3,5,6-tetrachloro- nitrobenzene to rabbits. Very small amt of tetrachloroaniline, mercapturic acid, free 4-amino-2,3,5,6-tetrachlorophenol, a sulfate, and a glucuronide were excreted in urine.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠中产生S-(2,3,5,6-四氯苯基)谷胱甘肽。/根据表格/

Yields S-(2,3,5,6-tetrachlorophenyl)glutathione in rat. /From table/

来源:Hazardous Substances Data Bank (HSDB)

代谢

巯基尿酸结合物在给兔子服用1-3克泰纳氮后48小时内的排泄率为11%。其他排泄出的代谢物包括一种醚葡萄糖苷酸（12%）、2,3,5,6-四氯苯胺（10%）、未结合的4-氨基-2,3,5,6-四氯酚（2%）和一种醚硫酸盐（1%）。

Mercapturic acid conjugate was excreted at a rate of 11% within 48 hr of the administration of 1-3 g of tecnazene to rabbits. Other metabolites excreted included an ether glucuronide (12%), 2,3,5,6-tetrachloroaniline (10%), unconjugated 4-amino-2,3,5,6-tetrachlorophenol (2%) and an etheral sulfate (1%).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

皮肤致敏剂 - 一种可以诱导皮肤产生过敏反应的制剂。

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

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

毒理性

• 解毒与急救

立即急救：确保已经进行了充分去污。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、气囊面罩装置或口袋面罩，按训练进行操作。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，让患者向前倾或将其置于左侧（如果可能，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/

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

基本治疗：建立专利气道（如需要，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，协助通气。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）连续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的呕吐反射且不流口水，则用水冲洗口腔，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……。/毒物A和B/

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

高级治疗：对于昏迷、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受体激动剂，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）或乳酸钠林格氏液。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……。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……。/毒物A和B/

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)

毒理性

• 人类毒性摘录

职业性皮肤过敏已经在农业工作者中有所报告。

/OTHER TOXICITY INFORMATION/ Occupational dermal sensitivity has been reported in agricultural workers.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

[14C]tecnazene在大鼠体内的吸收、分布、代谢和排泄已经进行了研究。早期对未标记tecnazene的代谢研究也在大鼠、家兔、豚鼠和鸽子上进行。Tecnazene在所有物种中都被广泛代谢。在动物体内，硝基团被还原，产生2,3,5,6-四氯苯胺和4-氨基-2,3,5,6-四氯酚。这些代谢物以原形或，在酚的情况下，形成醚基葡萄糖苷酸或硫酸盐结合物后排泄在尿液中。硝基团可以被谷胱甘肽取代，导致另一种主要代谢物S-(2,3,5,6-四氯苯基)-N-乙酰半胱氨酸的形成，这种代谢物也会排泄在尿液中。

The absorption, distribution, metabolism and excretion of [14C]tecnazene has been studied in the rat. Earlier metabolism studies with unlabelled tecnazene were also carried out on the rat, rabbit, guinea pig and pigeon. Tecnazene is extensively metabolized in all species. In animals the nitro group is reduced, yielding 2,3,5,6-tetrachloroaniline and 4-amino-2,3,5,6- tetrachlorophenol. These metabolites are excreted in the urine as such or, in the case of the phenol, after the formation of ethereal glucuronide or sulfate conjugates. The nitro group can be replaced by glutathione, leading to the formation of another major metabolite, S-(2,3,5,6-tetrachlorophenyl)-Nacetylcysteine, which is also excreted in the urine.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

... [14C]tecnazene 及其代谢物在雄性和雌性大鼠体内的分布情况，这些大鼠的剂量为每千克体重 1 毫克。24小时后，14C 在肾脏、肝脏和鼻通道中的浓度最高。七天之后，14C 的残留物含量较低，但在雄性大鼠中通常略高，其中最高浓度在腹部脂肪（0.032 mg/kg，以 tecnazene 表示）、肾脏（0.016 mg/kg）、肺（0.016）、血液（0.014）和心脏（0.013 mg/kg）中。在雌性大鼠中，最高浓度为 0.011 mg/kg，在腹部脂肪、血液和卵巢中。七天之后，大鼠体内组织中存在的剂量总比例分别为雄性 0.13% 和雌性 0.05%。根据 24 小时和 48 小时的放射自显影以及 7 天的液体闪烁计数，组织中的 14C 浓度似乎随时间减少。

... the disposition of [14C]tecnazene and its metabolites was followed in male and female rats dosed at 1 mg/kg bw. After 24 hours the highest tissue concentrations of 14C were in the kidneys, liver and nasal passages of both sexes. After seven days 14C residues were low but generally slightly higher in males where the highest concentrations were found in the abdominal fat (0.032 mg/kg, expressed as tecnazene), kidneys (0.016 mg/kg), lungs (0.016), blood (0.014) and heart (0.013 mg/kg). In females, the highest concentration was 0.011 mg/kg in the abdominal fat, blood and ovaries. After seven days the total proportion of the dose present in the tissues was 0.13% and 0.05% in male and female rats respectively. The concentrations of 14C in the tissues appeared to decrease as a function of time on the evidence of autoradiograms at 24 and 48 hours and liquid scintillation counting at 7 days.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

家兔单次口服0.1-3.0克/只的剂量后，在3天内通过粪便排出了60-78%，而尿液占35-38%（主要是结合产物形式）。在0.01克/只的剂量下，22-30%通过粪便排出。

Rabbits receiving a single oral dose of 0.1-3.0 g/animal eliminated 60-78% in the feces within 3 days, while the urine accounted for 35-38% (primarily as conjugated products). At 0.01 g/animal, 22-30% was recovered in the feces.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  9
• 危险品标志：
  Xn,N
• 安全说明：
  S24,S26,S36/37/39,S37,S45,S60,S61
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  29071900
• RTECS号：
  DC0175000
• 包装等级：
  III
• 危险类别：
  8
• 危险品运输编号：
  UN 3077 9/PG 3

制备方法与用途

类别：农药

毒性分级：低毒

急性毒性：

• 口服 - 大鼠 LD50: 7500 毫克/公斤

可燃性危险特性： 燃烧时会产生有毒氯化物和氮氧化物气体

储运特性： 需存放在通风、低温干燥的库房内，并与食品原料分开储存运输

灭火剂： 干粉、泡沫、砂土

反应信息

• 作为反应物：
  描述：

  四氯硝基苯 在 sodium methylate 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2,3,5,6-四氯酚
  参考文献：
  名称：

  苯偶氮基团将氯和氟活化为亲核芳族取代基。区域选择性制备多取代苯胺

  摘要：

  使用苯基偶氮基团将邻氟和氯原子选择性活化为丙硫醇盐阴离子进行亲核芳族取代。这实现了三个取代的4-烷氧基苯胺的区域选择性合成。通过将实验NMR化学位移与经验预测值进行比较，可以确定取代的区域选择性。在取代基效应的背景下讨论了所观察到的底物的反应性。

  DOI：

  10.1016/j.tet.2005.01.023
• 作为产物：
  描述：

  1,2,4,5-四氯苯 在 甲烷磺酸 、 二氧化氮 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以92%的产率得到四氯硝基苯
  参考文献：
  名称：

  Ozone-Mediated Reaction of Polychlorobenzenes and Some Related Halogeno Compounds with Nitrogen Dioxide: A Novel Non-Acid Methodology for the Selective Mononitration of Moderately Deactivated Aromatic Systems

  摘要：

  在臭氧的存在下，最好使用美克磺酸作为催化剂，聚氯苯在低温下与二氧化氮选择性地单硝化，得到相应的聚氯硝基苯，在大多数情况下，几乎以定量产率得到。

  DOI：

  10.1055/s-1994-25586
• 作为试剂：
  描述：

  甲醇 、 monomethyl fumarate 在 四氯硝基苯 作用下， 生成 1,4-dimethyl but-2-enedioate
  参考文献：
  名称：

  我的酸哪里去了？了解成盐过程中甲醇中马来酸的自催化酯化反应

  摘要：

  在一批API马来酸盐被相应的马来酸单甲酯盐污染之后，已经研究了马来酸在甲醇中的酯化动力学。发现酯化反应是由H +催化的由马来酸电离产生的二价铁，产生了观察到的速率规律，与马来酸浓度有一个半阶的依赖关系。根据在一定温度范围内测得的速率常数，开发了一种预测模型，该模型将估计达到给定酯化度所需的时间与温度和马来酸浓度有关。还已经确定了马来酸单马来酸酯的马来酸催化酯化反应的速率常数。通过与三乙胺形成盐来中和马来酸会降低酯化速率，其方式与中和度一致。

  DOI：

  10.1021/op3001959

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。

表征谱图