1R,cis-RU 15525 | 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
• 英文名称: 1R,cis-RU 15525
• 英文别名: (5-benzylfuran-3-yl)methyl (1S,3R)-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-QJLCOAGJSA-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：

  在密封的贮藏器内，并放置于阴凉、干燥处避光保存。

• 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生物降解途径在不同哺乳动物物种之间变化不大，但会因结构的不同而有所差异。基本上，除虫菊素和胺菊酯主要是通过酸部分中的异丁烯基侧链和醇部分中不饱和侧链的氧化来分解，同时酯水解也起着重要作用，而对于其他拟除虫菊酯，则以酯水解为主。

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

拟除虫菊酯在摄入后据报道会在胃肠道中被灭活。在动物体内，拟除虫菊酯会迅速代谢成水溶性、无活性的化合物。

Pyrethrins are reportedly inactivated in the GI tract following ingestion. In animals, pyrethrins are rapidly metabolized to water soluble, inactive compounds. /Pyrethrins/

来源:Hazardous Substances Data Bank (HSDB)

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，可能会因为添加增效剂...如有机磷或氨基甲酸盐...而延迟...以确保致命效果。...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/肥大、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...的效果是叠加的。/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。 ... 对于意识清醒、咽反射正常且摄入了亚致死量除虫菊酯且没有其他有毒成分的人，可以通过使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、吸氧和必要时的人工呼吸支持。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)

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，请由医生进行治疗。由于拟除虫菊酯的挥发显然是导致面部感觉异常的原因，应采取严格措施（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。它们适用于现场条件下的皮肤应用。玉米油也有一定效果，但可能的副作用使得长期使用不太合适。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

• THIENYLPYRIDYLCARBOXAMIDES
  申请人：Dunkel Ralf

  公开号：US20110105564A1

  公开（公告）日：2011-05-05

  Novel thienylpyridylcarboxamides of the formula (I) The present application is also directed to a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and also novel intermediates and their preparation.

  新型噻吩基吡啶基羧酰胺的化学式（I） 本申请还涉及多种制备这些化合物的方法，以及它们用于控制不受欢迎的微生物的用途，还有新颖的中间体及其制备。
• N-ARYLAMIDINE-SUBSTITUTED TRIFLUOROETHYL SULFIDE DERIVATIVES AS ACARICIDES AND INSECTICIDES
  申请人：BAYER CROPSCIENCE AG

  公开号：US20140315898A1

  公开（公告）日：2014-10-23

  The present invention relates to novel N-arylamide-substituted trifluoroethyl sulfide derivatives of the formula (I) in which X 1 , X 2 , X 3 , X 4 , R 1 , R 2 , R 3 , n have the meanings given in the description—to their use as acaricides and insecticides for controlling animal pests and to processes and intermediates for their preparation

  本发明涉及公式（I）中的新型N-芳酰胺取代三氟乙基硫醚衍生物，其中X1、X2、X3、X4、R1、R2、R3、n的含义如描述所示—它们作为杀螨剂和杀虫剂用于控制动物害虫，并涉及其制备的过程和中间体。
• Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto
  申请人：Dow AgroSciences LLC

  公开号：US20180279612A1

  公开（公告）日：2018-10-04

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions against such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫具有杀虫效用的分子领域，用于生产此类分子的过程，用于此类过程的中间体，含有此类分子的杀虫组合物，以及使用此类杀虫组合物对抗此类害虫的过程。这些杀虫组合物可以用作螨虫剂、杀虫剂、螨虫剂、软体动物杀虫剂和线虫杀虫剂。本文件披露了具有以下式（“式一”）的分子。
• [EN] PLANT GROWTH REGULATION<br/>[FR] REGULATION DE LA CROISSANCE VEGETALE
  申请人：BAYER CROPSCIENCE GMBH

  公开号：WO2005107465A1

  公开（公告）日：2005-11-17

  The present invention relates to the use of a compound for plant growth regulation, preferably by application of the compound to plants, to the seeds from which they grow or to the locus in which they grow, in an effective plant growth regulating, preferably non-phytotoxic amount, which compound is a 3,4-disubstituted maleimide derivative of formula (I) or an agriculturally acceptable salt thereof, wherein: X is aryl or heteroaryl which groups are unsubstituted or substituted; Y is NH or a covalent bond; and Z is aryl or heteroaryl which groups are unsubstituted or substituted and a method for treatment of plants with such compounds in order to induce growth regulating responses.

  本发明涉及一种化合物用于植物生长调节，优选通过将该化合物施用于植物、它们生长的种子或它们生长的位置，以有效的植物生长调节，优选为非植物毒性量，该化合物是式(I)的3,4-二取代马来酰亚胺衍生物或其农业可接受的盐，其中：X是未取代或取代的芳基或杂环芳基；Y是NH或共价键；Z是未取代或取代的芳基或杂环芳基，以及使用这些化合物处理植物的方法，以诱导生长调节反应。
• [EN] MOLECULES HAVING PESTICIDAL UTILITY, AND INTERMEDIATES, COMPOSITIONS, AND PROCESSES, RELATED THERETO<br/>[FR] MOLÉCULES PRÉSENTANT UNE UTILITÉ EN TANT QUE PESTICIDE, ET LEURS INTERMÉDIAIRES, COMPOSITIONS ET PROCÉDÉS
  申请人：DOW AGROSCIENCES LLC

  公开号：WO2017040194A1

  公开（公告）日：2017-03-09

  This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions aga inst such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula ("Formula One").

  这份披露涉及具有对节肢动物门、软体动物门和线虫门害虫有用的分子领域，用于生产这种分子的过程，用于这种过程的中间体，含有这种分子的杀虫剂组合物，以及使用这种杀虫剂组合物对抗这些害虫的过程。这些杀虫剂组合物可以用作螨虫剂、杀虫剂、螨虫剂、软体动物杀虫剂和线虫杀虫剂。本文件披露了具有以下化学式（“化学式一”）的分子。