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 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-WTKPLQERSA-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)

代谢

Tefluthrin在肝脏中被微粒体羧酸酯酶迅速水解为其无活性的酸。随后，4'位置的醇发生进一步的降解和羟基化，氧化产生广泛的代谢物和醇成分。在代谢过程中存在一定的立体特异性，反式异构体比顺式异构体水解得更快，对于顺式异构体，氧化是更重要的代谢途径。Tefluthrin主要通过尿液以代谢物的形式排出，但有一部分以原形通过粪便排出。(L867)

Tefluthrin is hydrolyzed rapidly in the liver to its inactive acid by microsomal carboxylesterase. Further degradation and hydroxylation of the alcohol at the 4' position then occurs, and oxidation produces a wide range of metabolites and alcohol components. There is some stereospecificity in metabolism, with trans-isomers being hydrolyzed more rapidly than the cis-isomers, for which oxidation is the more important metabolic pathway. Tefluthrin is excreted mainly as metabolites in urine but a proportion is excreted unchanged in faeces. (L867)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

拟除虫菊酯通过延长神经细胞兴奋时钠通道门的开启阶段来发挥其作用。它们似乎与钠通道附近的膜脂质相结合，从而改变通道动力学。这阻止了神经中钠门的关闭，从而延长了膜电位恢复到静息状态的时间。重复的（感觉、运动）神经元放电和延长的负后电位产生了与DDT相似的效果，导致神经系统过度活跃，可能导致瘫痪和/或死亡。拟除虫菊酯的其他作用机制包括对抗γ-氨基丁酸（GABA）介导的抑制作用、调节尼古丁胆碱能传递、增强去甲肾上腺素的释放以及对钙离子的作用。(T18, L857)

Pyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. (T18, L857)

来源:Toxin and Toxin Target Database (T3DB)

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

• 致癌物分类

无致癌性迹象（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity (not listed by IARC). (L135)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

对于每一种类型的拟除虫菊酯，特氟硫磷的影响通常包括迅速出现的攻击性行为和对外界刺激的敏感性增加，随后出现细颤、伴有全身粗颤的倒地、体温升高、昏迷和死亡。在特氟硫磷中毒后，还可能出现感觉异常、严重的角膜损伤、低血压和心动过速，这些症状与过敏性反应有关。

As for every type I pyrethroids , tefluthrin effects typically include rapid onset of aggressive behavior and increased sensitivity to external stimuli, followed by fine tremor, prostration with coarse whole body tremor, elevated body temperature, coma, and death. Paresthesia, severe corneal damage, hypotension and tachycardia, associated with anaphylaxis can also occur following tefluthrin poisoning. (L857)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

吸入（L857）；口服（L857）；皮肤接触（L857）；眼睛接触（L857）。

Inhalation (L857) ; oral (L857) ; dermal (L857) ; eye contact (L857).

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

在大鼠和狗中，当给予1或10毫克/千克剂量时，大部分放射性物质未改变地出现在粪便中，而大部分尿液中代谢物是结合态的。大约30%的给药剂量在两种动物中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物质可能部分是由于胆汁排出。研究还表明，氧化作用先于酯体裂解。

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

• 作为反应物：
  描述：

  tefluthrin 在 甲酸铵 作用下， 以 甲醇 、 水 为溶剂， 生成 tefluthrin 、 Tefluthrin
  参考文献：
  名称：

  Novel Liquid Chromatography–Tandem Mass Spectrometry Method for Enantioseparation of Tefluthrin via a Box–Behnken Design and Its Stereoselective Degradation in Soil

  摘要：

  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.

  DOI：

  10.1021/acs.jafc.9b04888
• 作为产物：
  描述：

  2,3,5,6-四氟-4-甲基苯甲醇 、 cis-((Z)-2-chloro-3,3,3-trifluoro-prop-1-enyl)-2,2-dimethylcyclopropane acyl chloride 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以96.5%的产率得到tefluthrin
  参考文献：
  名称：

  Preparation of one intermediate for pyrethroids

  摘要：

  本文公开了制备拟除虫菊酯中间体2,3,5,6-四氟二甲醇苯的方法。其中一种制备2,3,5,6-四氟二甲醇苯的方法包括四氟对苯二甲酸酯的还原。本文还公开了多种还原工艺，这些工艺简单安全，能够高产高纯地制得产物。本文还公开了通过卤化、氢化和酯化制备特氟氰菊酯的工艺，其中以2,3,5,6-四氟二甲醇苯为原料。

  公开号：

  US20070055075A1

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] 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。