苯醚氰菊酯 | 39515-40-7

• 物质功能分类: 化学农药原药 - 杀虫剂 - 拟除虫菊脂杀虫剂
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 苯醚氰菊酯
• 中文别名: 苯氰菊酯；右旋苯醚氰菊酯；右旋-顺反式-2,2-二甲基-3-(2-甲基-1-丙烯基)环丙烷羧酸-(+/-)-2-氰基-3-苯氧基苄
• 英文名称: cyphenothrin
• 英文别名: α-cyano-3-phenoxy-benzyl 2,2-dimethyl-3R-(2'-methyl-1'-propenyl)-cyclopropane-1R-carboxylate；[cyano-(3-phenoxyphenyl)methyl] 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
• CAS: 39515-40-7
• 化学式: C₂₄H₂₅NO₃
• mdl: MFCD01960864
• 分子量: 375.467
• InChiKey: FJDPATXIBIBRIM-UHFFFAOYSA-N

物化性质

• 熔点：
  25°C
• 沸点：
  504.24°C (rough estimate)
• 密度：
  d2525 1.083
• 溶解度：
  可溶于氯仿、DMSO（微溶）、甲醇（微溶）
• 颜色/状态：
  Viscous yellow liquid
• 蒸汽压力：
  9.0X10-7 mm Hg at 20 °C (0.12 mPa)
• 稳定性/保质期：
  Stable under recommended storage conditions.
• 粘度：
  808.8 cP at 30 °C

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

代谢

体内和体外比较代谢研究显示，苯醚菊酯和苯氰菊酯的结果如下：（1）在体外（肝脏匀浆）和体内，苯氰菊酯和苯醚菊酯的顺式异构体比相应的反式异构体更快速地被水解，且顺式-苯氰菊酯被水解的程度大于顺式-苯醚菊酯。（2）血浆酯酶与肝脏酯酶的底物特异性不同，它将苯氰菊酯和苯醚菊酯的反式和顺式异构体水解到几乎相同的程度。根据体内和体外研究的结果，分子中引入的CN基团并未影响反式-苯氰菊酯的生物降解性，反而使得顺式-苯氰菊酯比顺式-苯醚菊酯更具生物降解性。这些体内代谢轮廓（酯水解速率，尿液和粪便中的排泄模式）可能主要取决于肝脏酯酶的活性和/或底物特异性。

In vivo and in vitro comparative metabolism studies of phenothrin and cyphenothrin showed the following results: (1) The trans isomers of cyphenothrin and phenothrin were hydrolyzed more rapidly in vitro (liver homogenates) and in vivo than the corresponding cis isomers, and cis-cyphenothrin was hydrolyzed to a larger extent than cis-phenothrin. (2) Plasma esterases showed a different substrate specificity form the liver esterases and hydrolyzed the trans and cis isomers of cyphenothrin and phenothrin to nearly the same extents. From the results of the in vivo and in vitro studies, the CN group introduced into the molecule did not affect the biodegradability of trans-cyphenothrin, but rather made cis-cyphenothrin more biodegradable than cis-phenothrin. These in vivo metabolic profiles (ester hydrolysis rate, excretion pattern into urine and feces) make be mainly determined by activity and/or substrate specificity of the liver esterases.

来源:Hazardous Substances Data Bank (HSDB)

代谢

(1) 醇部分2'-和4'-苯氧基位的氧化；(2) 酸部分异丁烯基和末端二甲基基团的氧化；(3) 酯键的断裂；(4) CN离子转化为SCN离子和CO2；(5) 将产生的羧酸和酚与葡萄糖醛酸、硫酸和甘氨酸结合。

Both the trans and cis isomers underwent the following major metabolic reactions: (1) oxidation at the 2'- and 4'-phenoxy positions of the alcohol moiety; (2) oxidation at the isobutenyl and the gem-dimethyl groups of the acid moiety; (3) cleavage of ester linkage; (4) conversion of the CN ion to SCN ion and CO2; and (5) conjugation of the resulting carboxylic acids and phenols with glucuronic acid, sulfuric acid, and glycine.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在摄入后，拟除虫菊酯类杀虫剂会在胃肠道的各种消化酶的作用下水解。然而，一小部分具有杀虫活性的化合物或其衍生物会被吸收，这通过它们的毒性和对肝脏的影响可以证明。拟除虫菊酯类杀虫剂也可能通过吸入或皮肤接触被吸收。它们迅速分布到大多数组织中，特别是高脂肪含量的组织，并在中枢和周围神经组织中浓缩。拟除虫菊酯类杀虫剂或其代谢物不被认为是储存在体内或在乳汁中排泄的，但关于这一问题的研究尚未使用现代方法。拟除虫菊酯类杀虫剂的主要代谢途径是中心酯键的水解，在多个位点发生氧化攻击以及结合反应，产生一系列初级和次级水溶性代谢物，这些代谢物通过尿液排泄。代谢过程被认为涉及非特定的微粒体羧酸酯酶和微粒体混合功能氧化酶，这些酶几乎存在于所有类型的组织中，尤其是在肝脏中的活性特别高。代谢物通过尿液和粪便排出。

Following ingestion, pyrethriods are hydrolysed by various digestive enzymes in the gastro-intestinal tract. However, a small portion of the insecticidally active compounds or its derivatives are absorbed, as shown by their toxicity and their effect on the liver. Pyrethriods may also be absorbed following inhalation or dermal contact. They are rapidly distributed to most tissues, particularly to those with a high lipid content, and are concentrated in central and peripheral nervous tissues. Pyrethriods or their metabolites are not known to be stored in the body or to be excreted in the milk, but no study of the matter has employed modern methods. The major metabolic pathways for pyrethriods are hydrolysis of the central ester bond, oxidative attacks at several sites, and conjugation reactions, to produce a complex array of primary and secondary water-soluble metabolites that undergo urinary excretion. Metabolism is believed to involve nonspecific microsomal carboxyesterases and microsomal mixed function oxidases, which are located in nearly all tissue types, with particularly high activities in the liver. Metabolites are excreted in the urine and faeces. (L857, L889)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

识别和使用：赛氟氯氰菊酯是一种Ⅱ型拟除虫菊酯。它被用作熏蒸剂、杀虫剂和兽药。人体研究：拟除虫菊酯中毒的症状表现为共济失调、失去协调、过度兴奋、抽搐和瘫痪。根据拟除虫菊酯的类型，观察到神经系统不同区域的重复放电和/或传导阻滞。Ⅱ型拟除虫菊酯如赛氟氯氰菊酯，在α-碳上含有氰基，导致神经膜去极化和阻塞，进而引起瘫痪。这种作用归因于神经膜钠通道的修饰，导致非常缓慢的门控动力学。动物研究：在动物中，30 mg/kg及以上的剂量下已观察到震颤和抽搐。在104周的小鼠口服研究中，没有统计上显著增加的肿瘤发生率。在兔子的发育研究中，没有观察到生殖或致畸效应。赛氟氯氰菊酯在沙门氏菌TA-1535、TA-1537、TA-1538、TA-98和TA-100以及大肠杆菌WP-2 uvrA的遗传毒性研究中呈阴性，无论是否存在代谢激活。生态毒性研究：在96小时内，几种剂量的赛氟氯氰菊酯对成年孔雀鱼（Lebistes reticulatus）的影响观察到，剂量为34.8、46.5、53.5或60微克/升，并检查了它们的鳃。所有赛氟氯氰菊酯剂量下最常见的改变是鳃片上皮层从鳃小片上抬起和一些坏死。还观察到由于水肿导致的次级小片退化、次级小片缩短和棒状小片。

IDENTIFICATION AND USE: Cyphenothrin is a type II pyrethroid. It is used as fumigant, insecticide, and veterinary medicine. HUMAN STUDIES: The symptoms of poisoning caused by pyrethroids are characterized by ataxia, loss of coordination, hyperexcitation, convulsions, and paralysis. Depending on the type of pyrethroid, repetitive discharges and/or conduction block are observed in various regions of the nervous system. Type II pyrethroids such as cyphenothrin contain a cyano group at the alpha-carbon cause nerve membrane depolarization and block leading to paralysis. The action is ascribed to modification of nerve membrane sodium channels which result in very slow gating kinetics. ANIMAL STUDIES: Tremors and convulsions have been noted in animals at 30 mg/kg and higher. There was no statistically significant increased incidence of neoplasms in oral studies for 104 weeks in mice. In developmental studies in rabbits there were no reproductive or teratogenic effects noted. Cyphenothrin was negative in genotoxicity studies with Salmonella typhimurium strains TA-1535, TA-1537, TA-1538, TA-98 and TA-100 and Escherichia coli WP-2 uvrA in the presence and absence of metabolic activation. ECOTOXICITY STUDIES: The histopathological effects of several doses of cyphenothrin were observed in adult guppies (Lebistes reticulatus) at 34.8, 46.5, 53.5 or 60 ug cyphenothrin/L for 96-hr and their gills were examined. The most common changes at all cyphenothrin doses were the lifting of the epithelial layer from gill lamellae and some necrosis. Degeneration of secondary lamellae due to edema, the shortening of secondary lamellae, and club-shaped lamellae were also observed.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

I型和B型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产生的效果非常相似的作用，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、调节尼古丁乙酰胆碱能传递、增强去甲肾上腺素的释放以及对钙离子的作用。它们还抑制钙通道和Ca2+、Mg2+-ATP酶。（T10, T18, L857）

Both type I and type II 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. They also inhibit calium channels and Ca2+, Mg2+-ATPase. (T10, T18, L857)

来源:Toxin and Toxin Target Database (T3DB)

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

拟除虫菊酯的影响通常包括攻击行为的迅速发作和对外界刺激的敏感性增加，随后出现细颤、全身粗颤的倒地、体温升高、昏迷和死亡。在拟除虫菊酯中毒后，还可能出现感觉异常、严重的角膜损伤、低血压和心动过速，伴随过敏性休克的症状。

Pyrethroid 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 pyrethriod poisoning. (L857)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

溢出到头部、面部和眼睛可能会导致疼痛、流泪、畏光、充血和结膜及眼睑水肿。吞食情况下会引起上腹部疼痛、恶心、呕吐、头痛、头晕、厌食、乏力、胸部紧束感、视力模糊、感觉异常、心悸、粗大的肌肉颤动和意识障碍。在严重中毒情况下，已经发生过伴有角弓反张和意识丧失的惊厥发作。(T10)

Spilling on the head, face and eyes can result in pain, lacrimation, photophobia, congestion, and edema of the conjunctiva and eyelids. Ingestion cases epigastric pain, nausea, vomiting, headache, dizziness, anorexia, fatigue, tightness in chest, blurred vision, paresthesia, palpitations, coarse muscular fasciculations, and disturbances of conciousness. In servere poisonings, convulsive attacks with opisthotonos and loss of conciousness have occurred. (T10)

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

(14)C组织残留量：在单次口服或皮下给药(14)C标记的反式和顺式氯氰菊酯制剂后7天进行测量。使用酸和醇标记的反式和顺式异构体的制剂，组织残留量通常非常低。另一方面，CN标记的制剂与其他标记制剂相比，显示出相对较高的组织残留。

(14)C tissue residue levels 7 days after single oral or subcutaneous administration of each of the (14)C-labeled preparations of trans- and cis-cyphenothrin were measured. With the acid- and alcohol-labeled preparations of the trans and cis isomers, the tissue residue levels were generally very low. On the other hand, the CN-labeled preparations showed relatively higher tissue residues than other labeled preparations.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

单次口服或皮下给药（14）C-顺式或反式-环苯菊酯，以酸或醇基团标记的大鼠在2-4毫克/千克的剂量下，几乎完全消除了动物体内的（14）C。主要排泄途径是尿液和粪便，对于酸或醇标记的制剂（CN组除外）。在给药后7天内，这些标记制剂的（14）C总回收率超过93%。另一方面，来自CN组的（14）C排泄较慢。此外，4-6%的（14）C以（14）CO2的形式呼出。反式和顺式异构体的总（14）C回收率为60-80%。反式和顺式异构体的三种标记制剂与口服给药相比，皮下给药的（14）C尿液排泄更多。

Single oral or subcutaneous administration of (14)C-trans or cis-cyphenothrin labeled in the acid or alcohol moiety to rats at 2-4 mg/kg resulted in almost complete elimination of the (14)C from the animal body. Major excretion routes with the acid- or alcohol- (except for the CN group) labeled preparation were the urine and feces. The total recovery of the (14)C within 7 days after administration of these labeled preparations was more than 93% in urine and feces. On the other hand, the (14)C derived from the CN group was more slowly excreted. In addition, 4-6% of the (14)C was expired as (14)CO2. The total (14)C recovery was 60-80% for the trans and cis isomers. The three labeled preparations of the trans and cis isomers showed more urinary excretion of the (14)C with subcutaneous than with oral administration.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  Xn,N
• 安全说明：
  S60,S61
• 危险类别码：
  R22,R50/53
• WGK Germany：
  3
• 海关编码：
  29269090
• 危险品运输编号：
  UN 2810
• 包装等级：
  III
• 危险类别：
  6.1

制备方法与用途

化学性质
这是一种清亮无色至淡黄色粘稠液体，相对密度为1.08，闪点为130℃。该物质在已烷中的溶解度为4.84g/100g，在甲醇中的溶解度为9.27g/100g，而不溶于水（<10mg/100g）。

用途
这种产品具有较强的触杀力、胃毒和残效性，并且有中等的击倒活性。适用于防治家庭、公共场所及工业区中的苍蝇、蚊虫、蟑螂等卫生害虫。特别对体型较大的蟑螂（如烟色大蠊和美洲大蠊）表现出高效性，同时还具有显著的驱赶作用。

在室内喷洒0.005%~0.05%浓度时，可以明显驱赶家蝇；而当浓度降至0.0005%~0.001%时，则能产生引诱效果。此外，该产品处理羊毛可有效防治袋谷蛾、幕谷蛾和单色毛皮等害虫，药效优于氯菊酯、甲氰菊酯、氰戊菊酯、丙炔菊酯和右旋苯醚菊酯。

在将该产品与氯菊酯、右旋苯醚、甲氰、氰戊等成分浸泡蚊帐进行防蚊试验中，发现浸泡9个月后的药效以该产品最佳。此外，制成烟熏剂对蟑螂有特效，并可用于气雾剂药物。

反应信息

• 作为反应物：
  描述：

  苯醚氰菊酯 生成 (RS)α-cyano-3-phenoxy-benzyl 2,2-dimethyl-3-formyl-cyclopropane-1-carboxylate
  参考文献：
  名称：

  HIYAMA, TAMEJIRO;FUJITA, MAKOTO

  摘要：

  DOI：
• 作为产物：
  描述：

  菊酰氯 生成 苯醚氰菊酯
  参考文献：
  名称：

  XIYAMA, TAMEHDZIRO;FUDZITA, MAKOTO

  摘要：

  DOI：

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。