Tefluthrin | 79538-32-2

• 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: (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1S,3S)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
• CAS: 79538-32-2
• 化学式: C₁₇H₁₄ClF₇O₂
• 分子量: 418.739
• InChiKey: ZFHGXWPMULPQSE-SZGBIDFHSA-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加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。它们在野外条件下应用于皮肤是安全的。玉米油也有一定效果，但可能的副作用以及持续使用使其不太合适。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：

  1,2,4,5-四氟苯 在 吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 22.5h， 生成 Tefluthrin
  参考文献：
  名称：

  [EN] NOVEL CRYSTALLINE FORM OF TEFLUTHRIN, PROCESS FOR ITS PREPARATION AND USE THEREOF
  [FR] NOUVELLE FORME CRISTALLINE DE TÉFLUTHRINE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION

  摘要：

  提供了化学式为(I)的特氟氰菊酯的晶体形式，晶体制备过程，通过各种分析方法对晶体进行分析，并使用晶体制备稳定的农药配方。还提供了各种溶剂对晶体形式制备条件的使用。

  公开号：

  WO2018218896A1

文献信息

• 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。
• Preparation of 4-methyl-2, 3, 5, 6-tetrafluorobenzyl alcohol
  申请人：Jones Heavon Raymond Vincent

  公开号：US20050054886A1

  公开（公告）日：2005-03-10

  A process for the preparation of 1,4-bis(hydroxymethyl)-2,3,5,6-tetrafluorobenzene comprising fluorinating 2,3,5,6-tetrachloroterephthalonitrile to obtain 2,3,5,6-tetrafluoroterephthalonitrile, hydrogenating 2,3,5,6-tetrafluoroterephthalonitrile to give 1,4-bis(aminomethyl)-2,3,5,6-tetrafluorobenzene and converting 1,4-bis(aminomethyl)-2,3,5,6-tetrafluorobenzene to 1,4-bis(hydroxymethyl)-2,3,5,6-tetrafluorobenzene.

  制备1,4-双(羟甲基)-2,3,5,6-四氟苯的过程包括氟化2,3,5,6-四氯对苯二腈以获得2,3,5,6-四氟对苯二腈，将2,3,5,6-四氟对苯二腈氢化以得到1,4-双(氨甲基)-2,3,5,6-四氟苯，并将1,4-双(氨甲基)-2,3,5,6-四氟苯转化为1,4-双(羟甲基)-2,3,5,6-四氟苯。
• Novel Liquid Chromatography–Tandem Mass Spectrometry Method for Enantioseparation of Tefluthrin via a Box–Behnken Design and Its Stereoselective Degradation in Soil
  作者：Yong Wen、Zhen Wang、Yingying Gao、Xuejun Zhao、Beibei Gao、Zhaoxian Zhang、Lianshan Li、Zongzhe He、Minghua Wang

  DOI：10.1021/acs.jafc.9b04888

  日期：2019.10.23

  A simple and eco-friendly dispersive solid-phase extraction method coupled with ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) was developed for the determination of the chiral pesticide tefluthrin in food and environmental samples. The response surface methodology was applied to optimize separation conditions. The elution order of tefluthrin enantiomers was Z-cis-(1S,3S)-(-)-tefluthrin and Z-cis-(1R,3R)-(+)-tefluthrin on a Lux Cellulose-1 chiral column was identified via a polarimeter and vibrating circular dichroism. The average recoveries in five matrices ranged from 76.9 to 107.6%, with intraday relative standard deviations (RSDs) less than 15.6% and interday RSDs less than 12.5% for two enantiomers. The enantioselective degradation was investigated via laboratory incubation experiments. Slightly enantioselective degradation was observed under aerobic conditions; (1S,3S)-tefluthrin degraded preferentially with the enantiomer fraction value of 0.57 at 120 days of incubation. No remarkable enantioselective degradation was observed under anaerobic and sterile conditions. It was the first time that pyrethroid pesticides were determined at the enantiomer levels via UPLC-MS/MS. This novel method was successfully applied for the enantioselective analysis of tefluthrin enantiomers in authentic samples, indicating its efficacy in investigating the environmental stereochemistry of tefluthrin in the food web and environment. It is of crucial importance to improve risk assessment and regulation of chiral pesticides in an agricultural system.
• PROCESSES FOR THE PREPARATION OF ESTERS
  申请人：Syngenta Limited

  公开号：EP2279162B1

  公开（公告）日：2012-01-04
• Nematicidal Compositions
  申请人：De Kerpel Jan Octaaf

  公开号：US20080146445A1

  公开（公告）日：2008-06-19

  The present invention concerns nematicidal compounds, their formulation as nematicidal composition and their use for controlling nematodes, preferably plant parasitic nematodes.