杀虫畏 | 22248-79-9

• 物质功能分类: 化学农药原药 - 杀虫剂 - 有机磷杀虫剂
• 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: 杀虫畏
• 中文别名: (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: gardona；stirofos；[(Z)-2-chloro-1-(2,4,5-trichlorophenyl)ethenyl] dimethyl phosphate
• CAS: 22248-79-9
• 化学式: C₁₀H₉Cl₄O₄P
• 分子量: 365.965
• InChiKey: UBCKGWBNUIFUST-YHYXMXQVSA-N

物化性质

• 熔点：
  97-98 °C(lit.)
• 沸点：
  399.5±42.0 °C(Predicted)
• 密度：
  1.520±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于乙腈（少许）、甲醇（少许）
• 物理描述：
  Tetrachlorvinphos appears as colorless crystals or white powder. Somewhat corrosive. (NTP, 1992)
• 颜色/状态：
  Tan to brown crystalline solid
• 气味：
  ... Mild chemical odor. /Gardona/
• 蒸汽压力：
  4.20X10-8 mm Hg at 20 °C
• 稳定性/保质期：
  STABLE TO LESS THAN 100 °C; SLOWLY HYDROLYZED IN WATER, 50% LOSS OCCURRING @ 50 °C IN 1300 HR @ PH 3, IN 1060 HR @ PH 7, IN 80 HR @ PH 10.5 /TECHNICAL PRODUCT/
• 分解：
  When heated to decomposition it emits toxic fumes of /hydrogen chloride and phosphorous oxides/.

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吸收较差，大多数靠近施用部位的残留物未被代谢。进入全身循环的残留物在远离施用部位的组织中被广泛代谢。在反刍动物经皮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，后者再转化为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 增补第7卷：致癌性的整体评估：对国际癌症研究机构专著第1至42卷的更新，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

单次口服给予大鼠(14)C标记的毒死蜱...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，可能是作为(14)CO2。

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

• 危险品标志：
  F,N,Xn
• 安全说明：
  S16,S36,S36/37,S60,S61
• 危险类别码：
  R21/22
• 海关编码：
  2919900090
• 危险品运输编号：
  UN 3077 9/PG 3
• RTECS号：
  TB9100000
• 包装等级：
  I; II; III
• 危险类别：
  6.1

制备方法与用途

毒性 大鼠急性经口LD₅₀为4000～5000mg/kg；小鼠急性经口LD₅₀>5000mg/kg；兔急性经皮LD₅₀>2500mg/kg。2年饲喂试验表明，大鼠无用剂量为125mg/kg饲料，狗为200mg/kg饲料。鲤鱼LC₅₀为1～4mg/L，野鸭急性经口LD₅₀>2000mg/kg。

化学性质 本品为白色结晶，熔点（m.p.）97～98℃，蒸气压1.999×10^-4Pa (25℃)。在有机溶剂中溶解度较高：氯仿40%， 丙酮＜20%， 二甲苯＜15%；在水中溶解度为11mg/L。50℃时，水解半衰期分别为pH值3时1300h、pH值7时1060h和pH值10.5时80h。工业品纯度98%，顺式异构体含量较高。

用途 高效、低毒有机磷杀虫剂，主要以触杀作用为主，对鳞翅目、双翅目及多种鞘翅目害虫有显著效果。在有机磷杀虫剂抗性问题上，国际已将其视为重要替代品种。适用于粮、棉、果、茶、蔬菜和林业等领域，也可用于防治仓贮粮、织物害虫等。例如，在防治水稻二化螟时，以15g有效成分/100 m²施药两次，杀虫效果可达90%；用0.05%药液防治蓟马，效果达97%；用0.04%质量分数药液防治棉蚜，效果达98%，使用0.025%药液喷雾防治棉红蜘蛛，效果达94%。

用途 还可用于防治鳞翅目和双翅目害虫、牛奶棚和家畜笼中的蝇、仓库、牧场和森林害虫等，也可作为防蛾剂使用。

生产方法 五氯苯乙酮的制备：将三氯乙烯与少量偶氮二异丁腈（催化剂）于100℃通入干燥氧气，在6.5×10⁵Pa压力下于110℃反应10h，得二氯乙酰氯。然后滴入1, 2, 4-三氯苯和无水三氯化铝浆状物中，升温至90℃维持4h，制得五氯苯乙酮，收率可达79.87%，¹⁵D值为1.5854～1.5930。

亚磷酸三甲酯的制备：苯酚与三氯化磷反应生成亚磷酸三苯酯，然后在甲醇钠存在下与过量无水甲醇进行酯交换反应（温度130～150℃），用过量甲醇蒸气从塔顶带出产物。经蒸馏分离后回收甲醇和三甲酯，苯酚循环使用。

杀虫畏的合成：五氯苯乙酮投入反应锅中，在30～50℃滴入亚磷酸三甲酯，再升温至110℃保温反应0.5h，用乙醇（或乙醚和戊烷）处理得产品，收率达77.13%。

类别 农药

毒性分级 高毒

急性毒性 口服-大鼠 LD₅₀: 480 毫克/公斤；口服-小鼠 LD₅₀: 1379 毫克/公斤

可燃性危险特性 明火下易燃；受热分解产生有毒的氧化磷和氯化物气体

储运特性 库房需通风、低温干燥；与食品原料分开储运

灭火剂 砂土、干粉、泡沫

职业标准 STEL 1 毫克/立方米

文献信息

• [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] 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。

表征谱图