甲氰菊酯 | 39515-41-8

• 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: 甲氰菊酯
• 中文别名: 灭扫利；甲氰菊酯乳剂；2-氰基-3-苯氧基苄基-2,2,3,3-四甲基环丙烷酸酯；(RS)-alpha-氰基-3-苯氧苄基-2,2,3,3-四甲基环丙烷羧酸酯；中西农家庆；(RS)-α-氰基-3-苯氧苄基-2,2,3,3-四甲基环丙烷羧酸酯；alpha-氰基-3-苯氧基苄基-2,2,3,3-四甲基环丙烷羧酸酯；农螨丹；腈甲菊酯；分扑菊；2-氰基-3-苯氧基苄基-2,2,3,3-四甲基环丙烷酸酯(20%)
• 英文名称: fenpropathrin
• 英文别名: α-Cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropane-1-carboxylate；Danitol；(RS)-α-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate；(RS)-α-cyano-3-phenoxybenzyl-2,2,3,3-tetramethylcyclopropanecarboxylate；(RS)-α-cyano-3-phenoxybenzyl2,2,3,3-tetramethylcyclopropanecarboxylate,；α-cyano-3-phenoxybenzyl-2,2,3,3-tetramethylcyclopropanecarboxylate；[cyano-(3-phenoxyphenyl)methyl] 2,2,3,3-tetramethylcyclopropane-1-carboxylate
• CAS: 39515-41-8
• 化学式: C₂₂H₂₃NO₃
• mdl: MFCD00144305
• 分子量: 349.43
• InChiKey: XQUXKZZNEFRCAW-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：

  常规情况下不会分解，也没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

代谢

fenproponate在大鼠体内的代谢涉及迅速的氧化酶催化的酯裂解，随后是羟基化。

Metabolism of fenproponate in rats involves rapid oxidase catalyzed ester cleavage followed by hydroxylation.

来源:Hazardous Substances Data Bank (HSDB)

代谢

...基本上，除虫菊素和丙烯菊酯主要通过氧化酸部分中的异丁烯基侧链和醇部分中的不饱和侧链以及酯水解来分解，而在其他拟除虫菊酯中，酯水解占主导地位。

The metabolic pathways for the breakdown of the pyrethroids vary little between mammalian species but vary somewhat with structure. ... Essentially, pyrethrum & allethrin are broken down mainly by oxidation of the isobutenyl side chain of the acid moiety & of the unsaturated side chain of the alcohol moiety with ester hydrolysis playing & important part, whereas for the other pyrethroids ester hydrolysis predominates. /Pyrethrum and pyrethroids/

来源:Hazardous Substances Data Bank (HSDB)

代谢

哺乳动物对拟除虫菊酯的相对抗性几乎完全归因于它们能够迅速将拟除虫菊酯水解为其不活性的酸和醇成分，因为直接注射到哺乳动物的中央神经系统会导致与昆虫中观察到的相似易感性。恒温生物的一些额外抗性也可以归因于拟除虫菊酯的作用负温度系数，这意味着在哺乳动物体温下毒性较低，但主要效果是代谢性的。拟除虫菊酯的代谢消除非常迅速，这意味着通过静脉注射的毒性很高，通过较慢的口服吸收毒性适中，而通过皮肤吸收的毒性通常很低。/拟除虫菊酯/

The relative resistance of mammals to the pyrethroids is almost wholly attributable to their ability to hydrolyze the pyrethroids rapidly to their inactive acid & alcohol components, since direct injection into the mammalian CNS leads to a susceptibility similar to that seen in insects. Some additional resistance of homeothermic organisms can also be attributed to the negative temperature coefficient of action of the pyrethroids, which are thus less toxic at mammalian body temperatures, but the major effect is metabolic. Metabolic disposal of the pyrethroids is very rapid, which means that toxicity is high by the iv route, moderate by slower oral absorption, & often unmeasureably low by dermal absorption. /Pyrethroids/

来源:Hazardous Substances Data Bank (HSDB)

代谢

最快的水解和氧化攻击发生在具有反式取代基的初级醇酯上。对于所有的次级醇酯和初级醇顺式取代的环丙烷甲酸酯，氧化攻击是主要的。/拟除虫菊酯/

FASTEST BREAKDOWN IS SEEN WITH PRIMARY ALCOHOL ESTERS OF TRANS-SUBSTITUTED ACIDS SINCE THEY UNDERGO RAPID HYDROLYTIC & OXIDATIVE ATTACK. FOR ALL SECONDARY ALCOHOL ESTERS & FOR PRIMARY ALCOHOL CIS-SUBSTITUTED CYCLOPROPANECARBOXYLATES, OXIDATIVE ATTACK IS PREDOMINANT. /PYRETHROIDS/

来源:Hazardous Substances Data Bank (HSDB)

代谢

Fenpropathrin口服给药后吸收良好，广泛代谢，并以极性结合物形式在尿液中排出。主要的代谢途径正如预期，是通过酯键的水解。环丙烷羧酸部分随后以葡萄糖醛酸结合物的形式通过尿液排出。

Fenpropathrin has been shown to be well absorbed after oral administration, extensively metabolized, and eliminated as polar conjugates in urine. The main route of metabolism was, as anticipated, via hydrolysis of the ester linkage. The cyclopropane-carboxylic acid moiety was subsequently excreted via the urine as the glucuronide conjugate. (L857)

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：不太可能对人类致癌

Cancer Classification: Not likely to be carcinogenic to humans

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

在高剂量下，可以归因于甲氰菊酯的中毒迹象包括大量流涎和肺水肿、阵挛性惊厥、角弓反张（即脊柱向前弯曲，以至于仰卧的身体靠头部和脚跟支撑）、昏迷和死亡。在较低剂量下，常见的影响包括感觉异常和红斑。

At high doses, signs of poisoning attributable to fenpropathrin include profuse salivation and pulmonary edema, clonic seizures, opisthotonos (i.e., the spine is bent forward such that a supine body rests on its head and heels), coma, and death. At lower doses, commonly observed effects include paresthesia and erythema. (L863)

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

/PYRETHROIDS/迅速渗透昆虫外壳，正如通过在美洲大蠊（蟑螂）体表施用的LD50所显示的... /PYRETHROIDS/

/PYRETHROIDS/ READILY PENETRATE INSECT CUTICLE AS SHOWN BY TOPICAL LD50 TO PERIPLANETA (COCKROACH) ... /PYRETHROIDS/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

当放射性拟除虫菊酯通过口服给予哺乳动物时，它会被动物的小肠吸收并分布到所有被检查的组织中。给予大鼠转位异构体的放射性排泄情况如下：剂量：500毫克/千克；间隔：20天；尿液：36%；粪便：64%；总计：100%。/拟除虫菊酯/

WHEN RADIOACTIVE PYRETHROID IS ADMIN ORALLY TO MAMMALS, IT IS ABSORBED FROM INTESTINAL TRACT OF THE ANIMALS & DISTRIBUTED IN EVERY TISSUE EXAMINED. EXCRETION OF RADIOACTIVITY IN RATS ADMIN TRANS-ISOMER: DOSAGE: 500 MG/KG; INTERVAL 20 DAYS; URINE 36%; FECES 64%; TOTAL 100%. /PYRETHROIDS/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

拟除虫菊酯通过完整皮肤局部应用时可以被吸收。当动物接触到含有增效剂胡椒基丁氧基的拟除虫菊酯气溶胶时，这种组合很少或没有系统性吸收。/拟除虫菊酯/

Pyrethrins are absorbed through intact skin when applied topically. When animals were exposed to aerosols of pyrethrins with piperonyl butoxide being released into the air, little or none of the combination was systemically absorbed. /Pyrethrins/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

尽管有限的吸收可能是某些拟除虫菊酯类低毒性的原因，但通过哺乳动物肝脏酶（酯水解和氧化）的快速生物降解可能是主要负责因素。大多数拟除虫菊酯代谢物会迅速被肾脏至少部分排出。/拟除虫菊酯/

Although limited absorption may account for the low toxicity of some pyrethroids, rapid biodegradation by mammalian liver enzymes (ester hydrolysis and oxidation) is probably the major factor responsible. Most pyrethroid metabolites are promptly excreted, at least in part, by the kidney. /Pyrethroids/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 储存条件：
  密封、阴凉、干燥保存

制备方法与用途

制备方法

1. 2,2,3,3-四甲基环丙烷甲酰氯在正庚烷、水及相转移催化剂存在下，与间苯氧基苯甲醛、氰化钠反应，即得甲氰菊酯。原料消耗定额：菊酸110kg/t、醚醛800kg/t。
2. 同样的步骤可以重复进行，产物相同。

合成制备方法

1. 2,2,3,3-四甲基环丙烷甲酰氯在正庚烷、水及相转移催化剂存在下，与间苯氧基苯甲醛、氰化钠反应，即得甲氰菊酯。原料消耗定额：菊酸110kg/t、醚醛800kg/t。

反应信息

• 作为反应物：
  描述：

  甲氰菊酯 生成 2,2,3,3-四甲基环丙甲酸
  参考文献：
  名称：

  TAKAHASHI, NAOHIRO;MIKAMI, NOBUYOSHI;YAMADA, HIROHIKO;MIYAMOTO, JUNSHI, PESTIC. SCI., 1985, 16, N 2, 113-118

  摘要：

  DOI：
• 作为产物：
  描述：

  间苯氧基苯甲醛 在 吡啶 、 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 甲氰菊酯
  参考文献：
  名称：

  Development of an Enzyme-Linked Immunosorbent Assay for the Detection of the Pyrethroid Insecticide Fenpropathrin

  摘要：

  A competitive enzyme-linked immunosorbent assay (ELISA) was developed for the quantitative detection of fenpropathrin [(RS)-alpha-cyano-3-phenoxybenzyl-2,2,3,3-tetramethylcyclopropanecarboxylate]. Polyclonal antisera were isolated from rabbits immunized with two different fenpropathrin hapten conjugates. One hapten contained an amino function; the other contained a carboxyl group for conjugation to carrier proteins. Mollusk hemocyanins, thyroglobulin, and fetuin were used as carrier proteins. The antisera varied greatly in their affinities for fenpropathrin. A homologous assay system using the coating antigen format was the most sensitive. The IC50 for fenpropathrin was 20 mu g/L, and the lower detection limit was 2.5 mu g/L. Pyrethroids, such as phenothrin, permethrin, resmethrin, fenvalerate, deltamethrin, cyfluthrin, and cypermethrin, and the pyrethroid metabolites, 3-phenoxybenzoic acid and fenpropathrin acid, did not cross-react significantly in this assay. Ten percent acetone or methanol and a pH of 4 were determined to be optimum assay conditions. Various cationic, anionic, and nonionic detergents had no significant effect on the assay.

  DOI：

  10.1021/jf9710847

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。

表征谱图