克敌菊酯 | 58769-20-3

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 克敌菊酯
• 中文别名: 右旋-顺式-2,2-二甲基-3(2,2,4,5-四氢-2-氧代-噻嗯-3-叉甲基)环丙烷羧酸(E)-5-苄基-3-呋喃甲基酯；击倒菊酯；硫戊苄呋菊酯；噻嗯菊酯；噻吩菊酯；噻恩菊酯
• 英文名称: Spray-tox
• 英文别名: (5-benzylfuran-3-yl)methyl (1R,3S)-2,2-dimethyl-3-[(E)-(2-oxothiolan-3-ylidene)methyl]cyclopropane-1-carboxylate
• CAS: 58769-20-3
• 化学式: C₂₃H₂₄O₄S
• 分子量: 396.5
• InChiKey: UGWALRUNBSBTGI-ZKMZRDRYSA-N

物化性质

• 熔点：
  31℃
• 沸点：
  526.2±50.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)
• 闪点：
  100 °C
• 颜色/状态：
  Yellow-brown viscous oil
• 溶解度：
  Practically insol in water. Sol in dichloromethane, ethanol (10 g/kg), benzene, toluene, xylene, acetone, piperonyl butoxide. Slightly sol in kerosene.
• 稳定性/保质期：

  Hydrolyzed by aqueous alkalis. Rapidly decomposed by light (more slowly in mineral oils). Unstable to heat.

• 旋光度：
  Specific rotation: 16-19 deg

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  81.8
• 氢给体数：
  0
• 氢受体数：
  5

ADMET

代谢

在大鼠中，口服给药后，会发生快速的代谢（通过打开硫内酯环、酯键断裂和环羟基化）。

In rats, following oral administration, there is rapid metabolism (by opening of the thiolactone ring, cleavage of the ester, and ring hydroxylation)... .

来源:Hazardous Substances Data Bank (HSDB)

代谢

杀虫剂拟除虫菊酯的代谢途径在不同哺乳动物物种之间变化不大，但与结构有一定关系。基本上，除虫菊素和驱蚊菊酯主要通过氧化酸的异丁烯基侧链和醇的不饱和侧链，以及酯水解发挥重要作用，而对于其他拟除虫菊酯，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 an 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跃的酸和醇成分，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看到的相似易感性。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，通过皮肤吸收的毒性通常非常低。/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酸的初级醇酯上。对于所有次级醇酯和初级醇顺式取代环丙烷甲酸酯，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)

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

• 相互作用

拟除虫菊酯类物质的解毒...在苍蝇中很重要，可能由于添加了增效剂...如有机磷或氨基甲酸酯...来保证致死效果而延迟。...拟除虫菊酯类物质

/Pyrethroid/ detoxification ... important in flies, may be delayed by the addition of synergists ... organophosphates or carbamates ... to guarantee a lethal effect. ... /Pyrethroid/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

胡椒基丁醚通过抑制负责在节肢动物中代谢除虫菊酯的水解酶，从而增强除虫菊酯的杀虫活性。当胡椒基丁醚与除虫菊酯结合使用时，后者的杀虫活性可增加2到12倍。

Piperonyl butoxide potentiates /insecticidal activity/ of pyrethrins by inhibiting the hydrolytic enzymes responsible for pyrethrins' metabolism in arthropods. When piperonyl butoxide is combined with pyrethrins, the insecticidal activity of the latter drug is increased 2-12 times /Pyrethrins/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

在1000 ppm杀虫剂和10000 ppm氧化胡椒基丁的饮食水平下...在大鼠肝细胞中的增大、边缘化和细胞质包涵体...仅在8天内就得到了很好的发展，但是...并没有达到最大。变化与剂量成正比，并且与DDT产生的变化相似。这两种物质的效果是累加的。/杀虫剂/

At dietary level of 1000 ppm pyrethrins & 10000 ppm piperonyl butoxide ... /enlargement, margination, & cytoplasmic inclusions in liver cells of rats/ were well developed in only 8 days, but ... were not maximal. Changes were proportional to dosage & similar to those produced by DDT. Effects of the 2 ... were additive. /Pyrethrins/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

添加剂（例如石油馏分），如果存在，对患者造成的毒性威胁大于活性成分本身。 ... 当存在石油馏分添加剂时，不应诱导呕吐。 ... 在没有其他有毒成分的情况下，意识清醒且咽喉反射正常的人摄入亚致死剂量的除虫菊酯后，可以通过服用吐根糖浆诱导呕吐，随后使用盐水泻药和活性炭悬浮液。 ... 肺部和过敏后遗症对症治疗，包括维持呼吸道通畅、吸氧和必要时提供呼吸支持。治疗支气管痉挛和过敏性休克的常规药物和管理方案可以使用。癫痫发作可以用地西泮治疗。 /除虫菊酯和合成拟除虫菊酯/

The additives (e.g. petroleum distillate), when present, represent a greater toxic threat to the patient than the active ingredient itself. ... Emesis should not be induced when petroleum distillate additives are present. ... The alert person with an intact gag reflex & a sublethal pyrethrum ingestion without other toxic constituents may have emesis induced by ipecac, followed by a saline cathartic & slurry of activated charcoal. ... Pulmonary & allergic sequelae are treated symptomatically with airway maintenance, oxygen, & ventilatory assistance as required. Standard drugs and management protocols may be used for treatment of bronchospasm & anaphylaxis. Seizures are treated with diazepam. /Pyrethrum and synthetic pyrethroids/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在大鼠中，口服给药后，存在……快速排泄。

In rats, following oral administration, there is ... rapid excretion.

来源:Hazardous Substances Data Bank (HSDB)

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。当动物接触到含有胡椒基丁氧基的拟除虫菊酯气溶胶时，这种混合物几乎没有或没有系统性吸收。/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的因素。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

• 危险品标志：
  N,Xn
• 安全说明：
  S13,S60,S61
• 危险类别码：
  R50/53,R20/21/22
• 危险品运输编号：
  UN 3082 9/PG 3

文献信息

• [EN] INSECTICIDAL TRIAZINONE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRIAZINONE INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2013079350A1

  公开（公告）日：2013-06-06

  Compounds of the formula (I) or (I'), wherein the substituents are as defined in claim 1, are useful as pesticides.

  式(I)或(I')的化合物，其中取代基如权利要求1所定义的那样，可用作杀虫剂。
• [EN] ISOXAZOLINE DERIVATIVES AS INSECTICIDES<br/>[FR] DÉRIVÉS D'ISOXAZOLINE EN TANT QU'INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2011101402A1

  公开（公告）日：2011-08-25

  The present invention relates to compounds formula (I), wherein P is P1, P2, heterocyclyl or heterocyclyl substituted by one to five Z; and wherein A1, A2, A3, A4, G1, R1, R2, R3, R4, R5, R6, R17, R18, R19 and R20 are as defined in claim 1; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (I), to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising the compounds of formula (I) and to methods of using the compounds of formula (I) to control insect, acarine, nematode and mollusc pests.

  本发明涉及化合物式（I），其中P为P1、P2、杂环烷基或被一到五个Z取代的杂环烷基；以及其中A1、A2、A3、A4、G1、R1、R2、R3、R4、R5、R6、R17、R18、R19和R20如权利要求1中所定义；或其盐或N-氧化物。此外，本发明涉及制备化合物式（I）的过程和中间体，包括化合物式（I）的杀虫剂、杀螨剂、杀线虫剂和杀软体动物剂组合物，以及使用化合物式（I）控制昆虫、螨虫、线虫和软体动物害虫的方法。
• ISOXAZOLINE DERIVATIVES AS INSECTICIDES
  申请人：Pitterna Thomas

  公开号：US20120316124A1

  公开（公告）日：2012-12-13

  The present invention relates to compounds formula (I), wherein P is P1, P2, heterocyclyl or heterocyclyl substituted by one to five Z; and wherein A 1 , A 2 , A 3 , A 4 , G 1 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 17 , R 18 , R 19 and R 20 are as defined in claim 1 ; or a salt or N-oxide thereof. Furthermore, the present invention relates to processes and intermediates for preparing compounds of formula (I), to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising the compounds of formula (I) and to methods of using the compounds of formula (I) to control insect, acarine, nematode and mollusc pests.

  本发明涉及化合物式（I），其中P为P1、P2、杂环烷基或被1至5个Z取代的杂环烷基；以及其中A1、A2、A3、A4、G1、R1、R2、R3、R4、R5、R6、R17、R18、R19和R20如权利要求1所定义；或其盐或N-氧化物。此外，本发明涉及制备化合物式（I）的过程和中间体，包括化合物式（I）的杀虫剂、杀螨剂、杀线虫剂和杀软体动物剂组合物，以及使用化合物式（I）控制昆虫、螨虫、线虫和软体动物害虫的方法。
• [EN] MICROBIOCIDAL QUINOLINE (THIO)CARBOXAMIDE DERIVATIVES<br/>[FR] DÉRIVÉS MICROBIOCIDES DE QUINOLÉINE (THIO)CARBOXAMIDE
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2019053010A1

  公开（公告）日：2019-03-21

  Compounds of the formula (I) wherein the subsitiuents are as defined in claim 1. Furthermore, the present invention relates to agrochemical compositions which comprise compounds of formula (I), to preparation of these compositions, and to the use of the compounds or compositions in agriculture or horticulture for combating, preventing or controlling infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi.

  式(I)中的化合物，其中取代基如权利要求1所定义。此外，本发明涉及包括式(I)化合物的农药组合物，制备这些组合物以及在农业或园艺中使用这些化合物或组合物来对抗、预防或控制植物、收获的农作物、种子或非生物材料受植物病原微生物，特别是真菌的侵害。
• [EN] DIHYDROFURAN DERIVATIVES AS INSECTICIDAL COMPOUNDS<br/>[FR] DÉRIVÉS DE DIHYDROFURANE EN TANT QUE COMPOSÉS INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2013026726A1

  公开（公告）日：2013-02-28

  The present invention provides compounds of formula I wherein Q is Q1 or Q2; A1, A2, A3 and A4 are independently of each other C-H, C-R7, or nitrogen; R1 is C1-C8haloalkyl; R2 is aryl or aryl substituted by one to five R11, or heteroaryl or heteroaryl substituted by one to five R11; and R3, R4, R5, R6 and R7 are as defined in the claims. The invention also provides methods of controlling insects, acarines, nematodes or molluscs which methods comprise applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I).

  本发明提供了式I的化合物，其中Q是Q1或Q2；A1、A2、A3和A4分别独立地为C-H、C-R7或氮；R1为C1-C8卤代烷基；R2为芳基或被1至5个R11取代的芳基，或者为杂环芳基或被1至5个R11取代的杂环芳基；以及R3、R4、R5、R6和R7如权利要求中所定义的。该发明还提供了控制昆虫、螨虫、线虫或软体动物的方法，该方法包括向害虫、害虫的生境或易受害虫侵害的植物施加式(I)的化合物的杀虫、杀螨、杀线虫或杀软体动物的有效量。