杀虫畏 | 22350-76-1

• 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: 杀虫畏
• 中文别名: (E)-2-氯-1-(2,4,5-三氯苯基)乙烯基二甲基磷酸酯；司替罗磷；(Z)-2-氯-1-(2,4,5-三氯苯基)乙烯基二甲基磷酸酯；杀虫威
• 英文名称: tetrachlorvinphos
• 英文别名: trans-2-chloro-1-(2,4,5-trichlorophenyl)-vinyl dimethyl phosphate；(E)-Tetrachlorvinphos；[(E)-2-chloro-1-(2,4,5-trichlorophenyl)ethenyl] dimethyl phosphate
• CAS: 22350-76-1
• 化学式: C₁₀H₉Cl₄O₄P
• 分子量: 365.965
• InChiKey: UBCKGWBNUIFUST-BJMVGYQFSA-N

物化性质

• 物理描述：
  Tetrachlorvinphos appears as colorless crystals or white powder. Somewhat corrosive. (NTP, 1992)
• 熔点：
  96.3333333333 °C
• 溶解度：
  less than 1 mg/mL at 73° F (NTP, 1992)
• 蒸汽压力：
  4.2e-08 mm Hg at 68 °F (NTP, 1992)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

代谢

单次低剂量（5 mg/kg）、单次高剂量（250 mg/kg）和一系列剂量（5 mg/kg）口服给予CD大鼠放射性标记的四氯化乙烯。它几乎被完全代谢，大部分标记在给药后48小时内通过尿液（46-60%）和粪便（38-56%）排出。只有少量在组织中找到。回收的未代谢母体化合物非常少。代谢过程产生了许多不同的代谢物，并没有全部被识别。在粪便中观察到的的主要代谢物是三氯苯乙醇，女性排出的这种代谢物（占总给药C的18-34%）比男性（占13-23%）在所有三个剂量水平上都多。三氯苯乙醇也在粪便中发现，男性中占4-7%，女性中占3-6%。尿液中的主要代谢物，三氯扁桃酸，在男性中排出19-26%，但在女性中只排出10-12%。在高剂量下，女性排出的去甲基四氯化乙烯（25%）比男性（11%）多。然而，对于低剂量组，男性和女性之间几乎没有差异，男性排出8%，女性排出7%。

Radiolabelled tetrachlorvinphos was given orally to CD rats as a single low dose (5 mg/kg), as a single high dose (250 mg/kg), and in a series of doses (5 mg/kg). It was almost completely metabolized and most of the label was excreted in urine (46-60%) and feces (38-56%) within 48 hours of dosing. Only minor amounts were found in the tissues. Very little unmetabolized parent compound was recovered. The metabolic processes produced a number of different metabolites which were not all identified. The major metabolite observed in feces was trichlorophenylethanol with females eliminating more of this metabolite (18-34% total administered C) than males (13-23%) at all three dosing levels. Trichlorophenylethandiol was also found in feces ranging from 4-7 % in males and 3-6 % in females. A major metabolite in urine, trichloromandelic acid, was excreted in males at 19-26% but only 10-12% in females. At the high dose, females excreted more (25%) desmethyl tetrachlorvinphos than males (11%). However, there was essentially no difference for the low dose group with males (8%) and females (7%.)

来源:Hazardous Substances Data Bank (HSDB)

代谢

反刍动物口服给药后残留物的定性性质已足够了解。在一项山羊代谢研究中，确定的主要代谢物是自由的1-(2,4,5-三氯苯基)乙醇，结合的1-(2,4,5-三氯苯基)乙醇和2,4,5-三氯苯乙酮。反刍动物口服给药后的拟议代谢途径涉及将四氯乙烯磷转化为三氯苯乙醇，后者与葡萄糖醛酸结合或进一步代谢为三氯苯乙酮。

The qualitative nature of the residue in ruminants following oral dosing is adequately understood. In a goat metabolism study the major metabolites identified were free 1-(2,4,5- trichlorophenyl)ethanol, conjugated 1-(2,4,5- trichlorophenyl)ethanol, and 2,4,5-trichloroacetophenone. The proposed metabolic pathway in ruminants following oral administration involves conversion of tetrachlorvinphos to trichlorophenylethanol, which is conjugated to glucuronide or further metabolized to trichloroacetophenone.

来源:Hazardous Substances Data Bank (HSDB)

代谢

同样，通过皮肤给药后反刍动物体内残留物的定性特性已经得到充分理解。确定的主要残留物包括母体四氯化亚磷酸、自由的1-(2,4,5-三氯苯基)-乙醇、结合的1-(2,4,5-三氯苯基)乙醇和2,4,5-三氯苯乙酮。

Also, the qualitative nature of the residue in ruminants following dermal application is adequately understood. The major residues identified were the parent tetrachlorvinphos, free 1-(2,4,5- trichlorophenyl)-ethanol, conjugated 1-(2,4,5- trichlorophenyl)ethanol, and 2,4,5-trichloroacetophenone.

来源:Hazardous Substances Data Bank (HSDB)

代谢

四氯乙烯砜通过皮肤的吸收较差，大多数紧邻应用部位的残留物未被代谢。进入全身循环的残留物在远离应用部位的组织中广泛代谢。在反刍动物经皮肤应用的拟议代谢途径中，四氯乙烯砜被代谢为1-(2,4,5-三氯苯基)乙醇，它与葡萄糖醛酸结合，或者转化为2,4,5-三氯乙酰苯，再转化为2,4,5-三氯苯甲酸。

Tetrachlorvinphos was poorly absorbed through the skin, and most residues adjacent to the application site were not metabolized. Residues that entered the general circulation were extensively metabolized in tissues distal to the application site. In the proposed metabolic pathway in ruminants following dermal application, tetrachlorvinphos was metabolized to either 1-(2,4,5- trichlorophenyl)ethanol, which is conjugated to glucuronic acid, or to 2,4,5-trichloroacetophenone, which is converted to 2,4,5- trichlorobenzoic acid.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

没有关于人类的数据。动物致癌性的证据有限。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. Limited 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

• 致癌物分类

国际癌症研究机构致癌物：四氯乙烯酚

IARC Carcinogenic Agent:Tetrachlorvinphos

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)

毒理性

• 致癌物分类

国际癌症研究机构专著：第30卷：(1983) 杂项杀虫剂 增刊第7卷：致癌性的总体评估：更新国际癌症研究机构专著第1至42卷，1987年；440页；ISBN 92-832-1411-0（已绝版） 第112卷： (2017) 一些有机磷杀虫剂和除草剂

IARC Monographs:Volume 30: (1983) Miscellaneous Pesticides Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print) Volume 112: (2017) Some Organophosphate Insecticides and Herbicides

来源:International Agency for Research on Cancer (IARC)

毒理性

• 副作用

其他毒物 - 有机磷

Other Poison - Organophosphate

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

吸收、分配和排泄

进行了一项研究，使用雄性CD大鼠，分别以0.01、0.1、1或5毫克/平方厘米的剂量给予放射性标记的四氯化乙烯，每个剂量组中的一部分大鼠在0.5、1、2、4或10小时时处死。此外，还有一组动物在72小时时处死，其中在10小时时清洗了皮肤。清洗了皮肤施用区域以回收未吸收的四氯化乙烯。然后，分析了皮肤、尿液、粪便和尸体中应用的四氯化乙烯总量的百分比。对于在10小时处死的组，84%的总应用量（0.1毫克/平方厘米）的四氯化乙烯在清洗中被回收，9.57%留在皮肤、尿液、粪便和尸体中。这个吸收值9.57%用于评估经皮暴露后的人类风险。吸收百分比随着暴露时间的延长而增加，通常随着剂量的增加而减少。实际吸收的四氯化乙烯量随着剂量的增加而增加。

A study was conducted with male CD rats using doses of 0.01, 0.1, 1, or 5 mg/sq cm radiolabeled tetrachlorvinphos, with some of each dose group sacrificed at 0.5, 1, 2, 4, or 10 hours. Additionally, there was a group of animals, sacrificed at 72 hours, in which the skin was washed at 10 hours. The area of the dermal application was washed to recover unabsorbed tetrachlorvinphos. Then, the skin, urine, feces, and carcass were analyzed for percent of total tetrachlorvinphos applied. For the group sacrificed at 10 hours, 84% of the total applied (0.1 mg/sq cm ) tetrachlorvinphos was recovered in the wash, and 9.57% remained in the skin, urine, feces, and carcass. This absorption value, 9.57%, is used for assessing human risk following dermal exposure. The percent absorption increased with the duration of exposure and generally decreased with increasing dose. The actual quantity of tetrachlorvinphos absorbed increased with increasing dose.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

产蛋鸡通过浸泡在0.5%或1.0%有效成分（AI）水悬浮液中的50%可湿性粉剂（WP）Stirofos配方来处理。Stirofos残留物在处理后1天内即可在蛋中检测到，并在浸泡后3天达到最高水平（低剂量和高剂量鸟分别为0.021和0.035 ppm）。此后，蛋中残留物的水平迅速下降，21天后没有样本含有可检测到的Stirofos量（小于0.004 ppm）...

Laying hens were treated with a wettable powder formulation of stirofos (Rabon, 2-chloro-1-(2,4,5-trichlorophenyl) vinyl dimethylphosphate) by dipping in a 0.5 or 1.0% actual ingredient (AI) water suspension of a 50% wettable powder (WP) stirfos formulation. Stirofos residues were detected in eggs within 1 day after treatment and reached maximum levels 3 days after dipping (0.021 and .035 ppm in the low- and high-dose birds, respectively). After that time, levels of residues in eggs declined rapidly and no sample contained detectable quantities (less than .004 ppm) of stirofos after 21 days...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

单次给大鼠口服标记有(14)C的四氯乙烯酚……在4天内几乎完全通过尿液排出（在第一个24小时内排出44-78%，在第二个24小时内排出4-15%）。放射性物质的78%通过尿液排出，16.5%通过粪便排出，0.5%通过呼出的空气排出，可能是以(14)CO2的形式。

Single oral dose to rats of (14)C-labelled tetrachlorvinphos ... almost completely eliminated in the urine in 4 days (44-78% during the first 24 hr and 4-15% during the second 24 hr). 78% of the radioactive material was excreted in urine, 16.5% in the feces and 0.5% in the expired air, probably as (14)CO2.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险类别码：
  R21/22
• 危险品运输编号：
  61874
• 包装等级：
  I; II; III
• 危险类别：
  6.1

反应信息

• 作为反应物：
  描述：

  杀虫畏 、 苄基三乙基氯化铵 、 溴化钠 、 乙腈 、 硫酸 以88%的产率得到
  参考文献：
  名称：

  PETNEHAZY, I.;SZAKAL, GY. TOKE, L., SYNTHESIS, BRD, 1983, N 6, 453-456

  摘要：

  DOI：

文献信息

• INHIBITORS OF POLYISOPRENYLATED METHYLATED PROTEIN METHYL ESTERASE
  申请人：Lamango Nazarius Saah

  公开号：US20090253640A1

  公开（公告）日：2009-10-08

  Inhibitors of the enzyme prenylated methylated protein methyl esterase (PMPMEase), the last step in the prenylation process for many eukaryotic proteins, having the general structure R 1 -X-A-B(R 2 )-Y or R 1 -X-A(R 2 )-B-Y, where R 1 is preferably a polyisoprenyl group, X is a linking group, Y is a group that promotes affinity interactions to the active site of PMPMEase and imparts hydrolysis resistance to the inhibitor, A and B are bridge atoms, and R 2 is a characteristic-providing substituent.

  抑制酶前醇基化蛋白甲基酯酶（PMPMEase）的化合物，这是许多真核蛋白质前醇化过程的最后一步，具有一般结构R1-X-A-B（R2）-Y或R1-X-A（R2）-B-Y，其中R1最好是多异戊烯基团，X是连接基团，Y是促进与PMPMEase活性位点的亲和作用并赋予抑制剂水解抗性的基团，A和B是桥接原子，R2是提供特征的取代基。
• An insecticidal and miticidal composition which contains a carbamate and an organic phosphorus compound, and a method of controlling insects and mites therewith
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0017738A1

  公开（公告）日：1980-10-29

  An insecticidal and miticidal composition in which 2-dimethylamino-5,6-dimethylpyrimidin-4-yl dimethylcarbamate and at least one organic phosphorus compound, methylcarbamate compound, or pyrethroid compound are mixed with an inert carrier.

  一种杀虫和杀螨剂组合物，其中 2-二甲基氨基-5,6-二甲基嘧啶-4-基二甲基氨基甲酸酯和至少一种有机磷化合物、甲基氨基甲酸酯化合物或拟除虫菊酯化合物与惰性载体混合。
• Compositions in powder form containing pesticides and suitable for treatment of household furnishings
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0061876A1

  公开（公告）日：1982-10-06

  A composition in powder form suitable for treatment of household furnishings, such as carpets, rugs, upholstery, floors, and the like, and readily removable therefrom which comprises an inorganic salt carrier, an agglomerating agent and a pesticidal agent capable of killing arthropods such as ticks, fleas, silver fish, cockroaches and the like. Other optional ingredients such as fragrances, anti-static agents, anti-soiling agents, deodorizers and the like may be conveniently included in the composition.

  一种粉末状的组合物，适用于处理地毯、地毯、室内装潢、地板等家居用品，并易于从其中清除，该组合物包括一种无机盐载体、一种凝结剂和一种杀虫剂，该杀虫剂能够杀死虱子、跳蚤、银鱼、蟑螂等节肢动物。其他可选成分，如香料、抗静电剂、防污剂、除臭剂等也可方便地加入组合物中。
• Granular pesticidal composition
  申请人：SUMITOMO CHEMICAL COMPANY LIMITED

  公开号：EP0847691A1

  公开（公告）日：1998-06-17

  This invention relates to a granular pesticidal composition coated with a thermosetting resin. Release of the pesticidal active ingredient in the granular pesticidal composition of the present invention is suitably controlled by appropriately changing the kind and amount of a thermosetting resin depending on use occasion, and durability of effect of the pesticidal active ingredient is obtained.

  本发明涉及一种涂有热固性树脂的颗粒状杀虫组合物。 通过根据使用场合适当改变热固性树脂的种类和用量，可以适当控制本发明颗粒状杀虫组合物中杀虫活性成分的释放，并获得杀虫活性成分的持久效果。
• Electronic ID database and detection method for pesticide compound in edible agro-products based on LC-Q-Orbitrap
  申请人：CHINESE ACADEMY OF INSPECTION AND QUARANTINE

  公开号：US11169128B2

  公开（公告）日：2021-11-09

  Disclosed is an electronic ID database and detection method for pesticide compound in edible agro-products based on LC-Q-Orbitrap. The electronic ID database includes a collection of various pesticides compound electronic ID information, intelligent matching values and collision energies. It is ordered according to the retention time in the electronic ID. The electronic ID contains pesticide compounds information, retention time, adduct ions information, fragment ions information, collision energies, and the optimal full scan mass spectrum. The detection method includes sample pre-treatment, setting LC-Q-Orbitrap operating conditions and sample pesticide residue screening. Setting LC-Q-Orbitrap operating conditions contain setting suitable chromatography and mass spectrometry conditions. In pesticide residue screening procedures, firstly, the retention time is used to find pesticide compounds electronic ID database. If matching, the corresponding electronic ID information is extracted. Then the intelligent matching value is compared, if it is same, the result is recorded and displayed, and the screening is completed.

  本发明公开了一种基于 LC-Q-Orbitrap 的食用农产品中农药化合物电子 ID 数据库及检测方法。电子 ID 数据库包括各种农药化合物电子 ID 信息、智能匹配值和碰撞能量的集合。它根据电子 ID 的保留时间进行排序。电子 ID 包含农药化合物信息、保留时间、加成离子信息、碎片离子信息、碰撞能量和最佳全扫描质谱。检测方法包括样品预处理、设置 LC-Q-Orbitrap 运行条件和样品农药残留筛选。设置 LC-Q-Orbitrap 运行条件包括设置合适的色谱和质谱条件。在农药残留筛选程序中，首先利用保留时间查找农药化合物电子 ID 数据库。如果匹配，则提取相应的电子 ID 信息。然后比较智能匹配值，如果相同，则记录并显示结果，完成筛选。