tefluthrin | 391634-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tefluthrin
• 英文别名: (Z)-(1R)-cis-tefluthrin；(2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R,3R)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
• CAS: 391634-71-2
• 化学式: C₁₇H₁₄ClF₇O₂
• 分子量: 418.739
• InChiKey: ZFHGXWPMULPQSE-UKSCLKOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  9

ADMET

代谢

在大鼠脂肪的研究中，一半的放射性残留物可以归因于母体，其余的残留物是由羟基化母体代谢物的脂肪酸酯的混合物组成。

In a study with rat fat, half of the radioactive residues could be attributed to the parent and the remaining residues consisted of a mixture of fatty acid esters of hydroxylated parent metabolites.

来源:Hazardous Substances Data Bank (HSDB)

代谢

物种对拟除虫菊酯类酯类毒性的敏感性似乎高度依赖于组织酯酶的性质、检测到的活动水平、底物特异性以及目标和非目标物种中遇到的水解速率。几乎所有物种的组织中发现的微粒体单加氧酶系统在哺乳动物中广泛参与每一种拟除虫菊酯酯的解毒，在昆虫和鱼类物种中也参与其中一些药物的解毒。/拟除虫菊酯酯/

Species susceptibility to pyrethroid ester toxicity would appear to be highly dependent on the nature of the tissue esterase, the level of activity detected, the substrate specificity, and rate of hydrolysis encountered in target and nontarget species. The microsomal monoxygenase system found in the tissues of almost all species is extensively involved in the detoxification of every pyrethroid ester in mammals and of some of these agents in insect and fish species. /Pyrethroid esters/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

癌症分类：尚未评估

Cancer Classification: Not Yet Evaluated

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

神经毒素 - 其他中枢神经系统神经毒素

Neurotoxin - Other CNS neurotoxin

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

毒理性

• 毒性数据

大鼠LC50 = 50毫克/立方米/4小时

LC50 (rat) = 50 mg/m3/4h

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

毒理性

• 相互作用

许多能够抑制组织酯酶的有机磷酯会增强多种物种对拟除虫菊酯酯类毒性的敏感性。/拟除虫菊酯酯类/

...Many organophosphorus esters that are capable of inhibiting tissue esterases potentiate pyrethroid ester toxicity in a variety of species. /Pyrethroid esters/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

皮肤去污。立即用肥皂和水清洗皮肤... 如果出现刺激或感觉异常效果，应通过医生获得治疗。由于拟除虫菊酯的挥发显然是导致面部感觉异常的原因，应采取强烈措施（通风、保护面罩和头罩）以避免蒸汽接触面部和眼睛。维生素E油制剂（dL-α-生育酚醋酸酯）在预防和停止感觉异常反应方面具有独特效果。它们适用于现场条件下的皮肤应用。玉米油也有一定效果，但可能的副作用使得长期使用不太合适。凡士林的效果不如玉米油。氧化锌实际上会加剧反应。/拟除虫菊酯/

Skin decontamination. Wash skin promptly with soap and water... . If irritant or paresthetic effects occur, obtain treatment by a physician. Because volatilization of pyrethroids apparently accounts for paresthesia affecting the face, strenuous measures should be taken (ventilation, protective face mask and hood) to avoid vapor contact with the face and eyes. Vitamin E oil preparations (dL-alpha tocopheryl acetate) are uniquely effective in preventing and stopping the paresthetic reaction. They are safe for application to the skin under field conditions. Corn oil is somewhat effective, but possible side effects with continuing use make it less suitable. Vaseline is less effective than corn oil. Zinc oxide actually worsens the reaction. /Pyrethroids/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在大鼠和狗中，当给予1或10毫克/千克的剂量时，大部分放射性物质未改变地出现在粪便中，而大多数尿代谢物是结合形式的。在大鼠和狗中，大约30%的给药剂量被吸收并通过尿液排出。在大鼠和狗中，单次剂量在48小时内排出，其中50-65%通过粪便，20-30%通过尿液。在大鼠中，胆汁瘘管实验表明，粪便中测得的放射性可能部分是由于胆汁排出。研究还表明，氧化作用发生在酯体裂解之前。

In both rats and dogs, when given either 1 or 10 mg/kg, most of the radioactivity was found in the feces unchanged and most urinary metabolites were conjugated. Approximately 30% of the administered dose was absorbed and excreted in the urine in both species. Single doses in both rats and dogs were excreted within 48 hours, 50-65% in feces and 20-30% in the urine. In rats, a biliary fistula experiment suggested that the radioactivity measured in the feces may be partially due to biliary excretion. Studies also suggest that oxidation precedes the ester body cleavage.

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为产物：
  描述：

  2,3,5,6-四氟-4-甲基苯甲醇 、 (+/-)-cis-Z-cyhalothric acid chloride 生成 tefluthrin
  参考文献：
  名称：

  Preparation of 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol

  摘要：

  一种制备4-甲基-2,3,5,6-四氟苯甲醇的方法，包括将4-甲基-2,3,5,6-四氟苯甲腈加氢成4-甲基-2,3,5,6-四氟苯甲胺，并将4-甲基-2,3,5,6-四氟苯甲胺转化为4-甲基-2,3,5,6-四氟苯甲醇。该方法还可包括进一步反应4-甲基-2,3,5,6-四氟苯甲醇与顺式-Z-3-(2-氯-1,1,1-三氟-2-丙烯基)-2,2-二甲基环丙烷羧酰氯形成特氟氰。同时，还声明了4-甲基-2,3,5,6-四氟苯甲胺及其盐。

  公开号：

  US06894195B2

文献信息

• SYSTEM FOR PROTECTING GOODS DURING TRANSPORT
  申请人：Stutz Susanne

  公开号：US20120328685A1

  公开（公告）日：2012-12-27

  A system for protecting stored goods in a container ( 10 ), comprises a cage-like structure ( 20 ) formed by at least one pesticide treated net ( 22 ), capable of enclosing the stored goods, wherein the cage like structure ( 20 ), further comprises means for suspending the pesticide treated nets ( 14, 28, 30, 32, 34 ), and means for opening and closing the cage-like structure ( 26 ) on at least one section ( 24 ) of the at least one net ( 22 ). The system is particularly useful for the transport of tobacco, coffee, dried fruits, cocoa, nuts, tea, cereals, vegetables, spices and animals.

  一个用于保护集装箱（10）中存放货物的系统，包括由至少一种经过杀虫剂处理的网（22）形成的类似笼子的结构（20），能够围住存放的货物，其中类似笼子的结构（20）进一步包括用于悬挂经过杀虫剂处理的网（14、28、30、32、34）的手段，以及用于在至少一种网（22）的至少一部分（24）上打开和关闭类似笼子结构（26）的手段。该系统特别适用于烟草、咖啡、干果、可可、坚果、茶叶、谷物、蔬菜、香料和动物的运输。
• Process for the preparation of enantiomerically pure pyrethroid insecticides
  申请人：——

  公开号：US20030199709A1

  公开（公告）日：2003-10-23

  A process for producing compounds of formula (VIIa) and (VIIb) wherein X is a leaving group; Y and Y 1 are idependently Cl or Br; and Z is Cl, Br or a haloalkyl group which process comprises a) reacting a compound of formula (VII) wherein X, Y, Y 1 and Z are as defined for compounds (VIIa) and (VIIb) with a substantially optically pure chiral amine in a solvent to form a diastereoisomeric salt; b) separating the diastereomeric salt of each enantiomer; c) converting the diastercomeric salt of each anantiomer separately to compounds of formulae (VIIa) and (VIIb) respectively by acid or base hydrolysis, the use of the compounds in making pyrethroid insecticides and novel intermediates.

  一种生产化合物的方法，其化学式为(VIIa)和(VIIb)，其中X是一个离去基团；Y和Y1分别是Cl或Br；Z是Cl、Br或卤代烷基，该方法包括：a)将化合物(VII)与定义为化合物(VIIa)和(VIIb)的X、Y、Y1和Z反应，反应溶剂中使用基本光学纯的手性胺形成一个对映异构盐；b)分离每个对映体的对映异构盐；c)通过酸或碱水解将每个对映异构盐分别转化为化合物的方法(VIIa)和(VIIb)，所述化合物用于制造拟除虫菊酯类杀虫剂和新颖的中间体。
• Preparation of 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol
  申请人：——

  公开号：US20040063993A1

  公开（公告）日：2004-04-01

  A process for the preparation of 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol comprising hydrogenating 4-methyl-2,3,5,6-tetrafluorobenzonitrile to 4-methyl-2,3,5,6-tetrafluorobenzylamine and converting 4-methyl-2,3,5,6-tetrafluorobenzylamine to 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol. The process optionally also comprises the further step of reacting 4-Methyl-2,3,5,6-tetrafluobenzyl alcohol with cis-Z-3-(2-chloro-1,1,1-trifluoro-2-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride to the form tefluthrin. 4-Methyl-2,3,5,6-tetrafluorobenzylamine and salts thereof are also claimed.

  一种制备4-甲基-2,3,5,6-四氟苯甲醇的方法，包括将4-甲基-2,3,5,6-四氟苯甲腈加氢制得4-甲基-2,3,5,6-四氟苯甲胺，然后将4-甲基-2,3,5,6-四氟苯甲胺转化为4-甲基-2,3,5,6-四氟苯甲醇。该方法还可以包括将4-甲基-2,3,5,6-四氟苯甲醇与顺式-Z-3-(2-氯-1,1,1-三氟-2-丙烯基)-2,2-二甲基环丙烷羧酰氯反应以形成特氟氰。同时还声明了4-甲基-2,3,5,6-四氟苯甲胺及其盐。
• Malononitrile compounds and their use as pesticides
  申请人：——

  公开号：US20040143007A1

  公开（公告）日：2004-07-22

  The present invention relates to malononitrile compounds of formula (Y): 1 wherein R 1 and R 2 are the same or different and independently C 1 -C 5 (halo)alkyl, C 2 -C 5 (halo)alkyloxy, C 2 -C 5 (halo)alkenyl, C 2 -C 5 (halo)alkynyl, hydrogen, or cyano; R 3 is C 3 -C 6 (halo)cycloalkyl; m is an integer of 1 to 3; R 5 is halogen, cyano, nitro, C 1 -C 4 (halo)alkyl, or the like; n is an integer of 0 to 4, with the proviso that when n is 2 or more, then R 5 's are the same or different from each other; R 6 is halogen, cyano, nitro, C 1 -C 4 (halo)alkyl, or the like; as well as pesticide compositions containing these compounds as active ingredients. The present invention makes it possible to effectively control pests such as insect pests, acarine pests, and nematode pests.

  本发明涉及式（Y）的马隆腈化合物：其中R1和R2相同或不同，独立地为C1-C5（卤）烷基，C2-C5（卤）烷氧基，C2-C5（卤）烯基，C2-C5（卤）炔基，氢或氰基；R3为C3-C6（卤）环烷基；m为1至3的整数；R5为卤素，氰基，硝基，C1-C4（卤）烷基或类似物；n为0至4的整数，但当n为2或更多时，则R5互相相同或不同；R6为卤素，氰基，硝基，C1-C4（卤）烷基或类似物；以及含有这些化合物作为活性成分的杀虫剂组合物。本发明使得有效控制害虫，如昆虫害虫，螨类害虫和线虫害虫成为可能。
• Synergistische insektizide Mischungen auf der Basis von Chlornicotinyl-Insektiziden
  申请人：Bayer CropScience AG

  公开号：EP1649750A2

  公开（公告）日：2006-04-26

  Die vorliegende Erfindung betrifft insektizide Mischungen von Chlornicotinyl-Insektiziden der Formel (I) in welcher R1für C1-C5-Alkyl steht, R2für Wasserstoff oder C1-C5-Alkyl steht oder R1 und R2 zusammen für -CH2-CH2-, -CH2-CH2-CH2- oder stehen, Xfür eine NH-Gruppe, NCH3-Gruppe oder für Schwefel steht, Yfür Stickstoff oder eine CH-Gruppe steht und Zfür Cyano oder Nitro steht, mit einem oder mehreren in der Beschreibung genannten Synergisten.

  本发明涉及式（I）的氯烟酰杀虫剂的杀虫混合物 其中 R1代表C1-C5-烷基、 R2 代表氢或 C1-C5 烷基 或 R1 和 R2 共同代表-CH2-CH2-、-CH2-CH2-CH2-或 代表 X 代表 NH 基团、NCH3 基团或硫、 Y 代表氮或 CH 基团，以及 Z 代表氰基或硝基、 以及说明中提到的一种或多种增效剂。