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(S) α-cyano-3-phenoxy-benzyl 2,2-dimethyl-3S-(1',2',2',2'-tetrabromoethyl)-cyclopropane-1R-carboxylate

中文名称
——
中文别名
——
英文名称
(S) α-cyano-3-phenoxy-benzyl 2,2-dimethyl-3S-(1',2',2',2'-tetrabromoethyl)-cyclopropane-1R-carboxylate
英文别名
[Cyano-(3-phenoxyphenyl)methyl] (1R,3S)-2,2-dimethyl-3-[(1S)-1,2,2,2-tetrabromoethyl]cyclopropane-1-carboxylate
(S) α-cyano-3-phenoxy-benzyl 2,2-dimethyl-3S-(1',2',2',2'-tetrabromoethyl)-cyclopropane-1R-carboxylate化学式
CAS
——
化学式
C22H19Br4NO3
mdl
——
分子量
665.014
InChiKey
YWSCPYYRJXKUDB-LUBNNEDASA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    8
  • 重原子数:
    30
  • 可旋转键数:
    7
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.36
  • 拓扑面积:
    59.3
  • 氢给体数:
    0
  • 氢受体数:
    4

ADMET

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,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 and 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 intravenous route, moderate by slower oral absorption, and often unmeasureably low by dermal absorption. /Pyrethroids/
来源:Hazardous Substances Data Bank (HSDB)
代谢
拟除虫菊酯通常通过哺乳动物的酯水解、氧化和结合进行代谢,并且没有在组织中积累的趋势。在环境中,拟除虫菊酯在土壤和植物中相当快速地降解。分子上各个位点的酯水解和氧化是主要的降解过程。/拟除虫菊酯/
Synthetic pyrethroids are generally metabolized in mammals through ester hydrolysis, oxidation, and conjugation, and there is no tendency to accumulate in tissues. In the environment, synthetic pyrethroids are fairly rapidly degraded in soil and in plants. Ester hydrolysis and oxidation at various sites on the molecule are the major degradation processes. /Pyrethroids/
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
  • 毒性总结
识别和使用:三氯甲菊酯是一种固体。它以前被用作杀虫剂。 人类暴露和毒性:吸入拟除虫菊酯类化合物(如三氯甲菊酯)的临床表现可能是局部或全身性的。局限于上呼吸道的局部反应包括鼻炎、打喷嚏、喉咙痒、口腔粘膜水肿,甚至喉粘膜水肿。下呼吸道的局部反应包括咳嗽、气短、喘息和胸痛。在敏感患者中,急性暴露会引起类似哮喘的反应。慢性暴露的个体可能会出现胸痛、咳嗽、呼吸困难、支气管痉挛的过敏性肺炎。动物研究:合成拟除虫菊酯是神经毒素,通过作用于哺乳动物和/或昆虫的钠通道与外周和中枢神经系统的轴突相互作用。单次剂量就会在哺乳动物中产生毒性迹象,如震颤、过度兴奋、流涎、舞蹈手足徐动症和瘫痪。在接近致死剂量水平,合成拟除虫菊酯会导致神经系统短暂变化,如下肢神经轴突肿胀和/或断裂以及髓鞘退化。它们不会被认为会引起某些有机磷化合物诱导的迟发性神经毒性。在为期2年的小鼠研究中,以10 mg/kg/天的剂量观察到以下效果:增加死亡率、增加行为效应、皮肤病变、增加食物和水的消耗、增加尿量、肝和肾重量暂时增加、在雄性和雌性中皮炎和肌炎。在一项代际繁殖研究中,将三氯甲菊酯以0、0.75、3.0和12.0 mg/kg/天的剂量水平每天通过灌胃给予大鼠。在任何剂量水平下都没有发现对F0或F1代父母生殖性能的有害影响。在F1仔鼠的12 mg/kg/天组中注意到了出生时初始体重的降低迹象。在F1和F2仔鼠的哺乳期间,在中和高剂量组观察到与剂量相关的仔鼠体重下降,而母鼠在3和12 mg/kg/天的剂量下体重下降。生态毒性研究:三氯甲菊酯对大型蚤(D. magna)有毒,其LC50为0.15微克/升。它对在施用后1小时接触处理叶子的蜜蜂没有毒性。
IDENTIFICATION AND USE: Tralomethrin is a solid. It was formerly used as an insecticide. HUMAN EXPOSURE AND TOXICITY: The clinical manifestations of inhalation exposure to pyrethrins, such as tralomethrin, can be local or systemic. Localized reactions confined to the upper respiratory tract include rhinitis, sneezing, scratchy throat, oral mucosal edema, and even laryngeal mucosal edema. Localized reactions of the lower respiratory tract include cough, shortness of breath, wheezing, and chest pain. An asthma-like reaction occurs with acute exposures in sensitized patients. Hypersensitivity pneumonitis characterized by chest pain, cough, dyspnea, and bronchospasm may occur in an individual chronically exposed. ANIMAL STUDIES: Synthetic pyrethroids are neuropoisons acting on the axons in the peripheral and central nervous systems by interacting with sodium channels in mammals and/or insects. A single dose produces toxic signs in mammals, such as tremors, hyperexcitability, salivation, choreoathetosis, and paralysis. At near-lethal dose levels, synthetic pyrethroids cause transient changes in the nervous system, such as axonal swelling and/or breaks and myelin degeneration in sciatic nerves. They are not considered to cause delayed neurotoxicity of the kind induced by some organophosphorus compounds. In 2 year mouse study at 10 mg/kg/day the following effects were observed: increased mortality, increased behavioral effects, skin lesions, increased food and water consumption, increased urine volume, transient increase in liver and kidney weights, dermatitis and myositis in male and female. In a generation reproduction study tralomethrin was administered daily by gavage to rats at dose levels of 0, 0.75, 3.0, and 12.0 mg/kg/day. No evidence of adverse effects on reproductive performance of either male or the female F0 or F1 parents were noted at any dose levels. Some signs of decreased initial body weight (at birth) were noted in the F1 pups in the 12 mg/kg/day group. Dose-related decreases in pup weights were observed during lactation in the F1 and F2 pups in the mid- and high- dose groups while the parent rats showed decreases in body weight at 3 and 12 mg/kg/day. ECOTOXICITY STUDIES: Tralomethrin was toxic to D. magna, with LC50 of 0.15 ug/L. It was not toxic to bees contacting treated foliage 1 hr after application.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 解毒与急救
立即用肥皂和水清洗皮肤...如果出现刺激或感觉异常,应请医生治疗。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、戴防护面罩和头罩)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。它们在野外条件下应用于皮肤是安全的。玉米油也有一定效果,但可能的副作用以及持续使用使其不太合适。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/
Decontaminate the 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)
毒理性
  • 解毒与急救
立即用大量清洁水或生理盐水冲洗眼睛以处理眼睛污染。一些拟除虫菊酯化合物可能对眼睛非常腐蚀,因此应采取特殊措施以避免眼睛污染。如果刺激持续存在,应获得专业眼科护理。/拟除虫菊酯/
Treat eye contamination immediately by prolonged flushing of the eye with copious amounts of clean water or saline.. Some pyrethroid compounds can be very corrosive to the eyes, so extraordinary measures should be taken to avoid eye contamination. If irritation persists, professional ophthalmologic care should be obtained. /Pyrethroids/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 解毒与急救
几种药物在缓解故意中毒的实验动物中观察到的拟除虫菊酯类神经毒性表现方面是有效的,但没有一种药物在人类中毒情况下进行过测试。因此,在这种情况下,这些药物的有效性或安全性都是未知的。此外,中度神经毒性症状和体征很可能会自行缓解。/拟除虫菊酯类/
Several drugs are effective in relieving the pyrethroid neurotoxic manifestations observed in deliberately poisoned laboratory animals, but none has been tested in human poisonings. Therefore, neither efficacy nor safety under these circumstances is known. Furthermore, moderate neurotoxic symptoms and signs are likely to resolve spontaneously. /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方式给予哺乳动物时,它会被动物的小肠吸收并分布到所有被检查的组织中。在大鼠中给予顺式异构体:剂量:500毫克/千克;间隔20天;尿液占36%,粪便占64%,总计100%。/拟除虫菊酯/
When radioactive pyrethroid is administered orally to mammals, it is absorbed from intestinal tract of the animals and 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
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的快速生物降解(酯水解和氧化)可能是这一现象的主要因素......大多数拟除虫菊酯代谢物会迅速被排泄,至少部分通过肾脏。/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 for this phenomenon ... Most pyrethroid metabolites are promptly excreted, at least in part, by the kidneys. /Pyrethroids/
来源:Hazardous Substances Data Bank (HSDB)

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    参考文献:
    名称:
    Phthalimidomethyl cyclopropane carboxylic acid esters
    摘要:
    化合物的名称为新型环丙烷羧酸酯,其化学式为##STR1##其中X1为氢、氟、氯和溴中的一种,X2为氟、氯和溴中的一种,X3为氯、溴和碘中的一种,R为##STR2##和苄基,可选地被替换为1至4个碳原子的烷基,2至6个碳原子的烯基,2至6个碳原子的烯氧基,4至8个碳原子的烯二烷基,亚甲二氧基,苯甲基和卤素中的至少一个成员。R1为氢和甲基中的一种,R2为单环芳基和--CH2--C.tbd.CH中的一种,R3为具有至少一个双键的2至6个碳原子的脂肪基,R4为氢、--CN和--C.tbd.CH中的一种,R5为氯和甲基中的一种,n为0、1或2,R6、R7、R8和R9分别为氢、氯和甲基中的一种,S/I表示环可以是芳香、二氢或四氢,具有杀虫性能,以及其制备方法。
    公开号:
    US04231932A1
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文献信息

  • Phthalimidomethyl cyclopropane carboxylic acid esters
    申请人:Roussel Uclaf
    公开号:US04231932A1
    公开(公告)日:1980-11-04
    Novel cyclopropane carboxylic acid esters of the formula ##STR1## wherein X.sub.1 is selected from the group consisting of hydrogen, fluorine, chlorine and bromine, X.sub.2 is selected from the group consisting of fluorine, chlorine and bromine, X.sub.3 is selected from the group consisting of chlorine, bromine and iodine and R is selected from the group consisting of ##STR2## and benzyl optionally substituted with at least one member of the group consisting of alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, alkadienyl of 4 to 8 carbon atoms, methylenedioxy, benzyl and halogens, R.sub.1 is selected from the group consisting of hydrogen and methyl, R.sub.2 is selected from the group consisting of monocyclic aryl and --CH.sub.2 --C.tbd.CH,R.sub.3 is an aliphatic of 2 to 6 carbon atoms having at least one double bond, R.sub.4 is selected from the group consisting of hydrogen, --CN and --C.tbd.CH, R.sub.5 is selected from the group consisting of chlorine and methyl, n is 0, 1 or 2, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are individually selected from the group consisting of hydrogen, chlorine and methyl and S/I indicates that the ring may be aromatic, dihydro or tetrahydro having pesticidal properties, and a process for their preparation.
    化合物的名称为新型环丙烷羧酸酯,其化学式为##STR1##其中X1为氢、氟、氯和溴中的一种,X2为氟、氯和溴中的一种,X3为氯、溴和碘中的一种,R为##STR2##和苄基,可选地被替换为1至4个碳原子的烷基,2至6个碳原子的烯基,2至6个碳原子的烯氧基,4至8个碳原子的烯二烷基,亚甲二氧基,苯甲基和卤素中的至少一个成员。R1为氢和甲基中的一种,R2为单环芳基和--CH2--C.tbd.CH中的一种,R3为具有至少一个双键的2至6个碳原子的脂肪基,R4为氢、--CN和--C.tbd.CH中的一种,R5为氯和甲基中的一种,n为0、1或2,R6、R7、R8和R9分别为氢、氯和甲基中的一种,S/I表示环可以是芳香、二氢或四氢,具有杀虫性能,以及其制备方法。
  • INSECTICIDAL COMPOSITION AND PRODUCTION THEREOF
    申请人:MITSUI TOATSU CHEMICALS, Inc.
    公开号:EP0543027A1
    公开(公告)日:1993-05-26
    An aqueous suspension of a microcapsular insecticidal composition is obtained by emulsifying a liquid pyrethroid insecticide or a hydrophobic solution comprising a pyrethroid insecticide and a high-boiling solvent, preferably an alkyl phthalate wherein the alkyl group has 8 to 13 carbon atoms, in the presence of a water-soluble anionic polymeric surfactant to obtain liquid particles having appropriate diameters and polycondensing melamine-formaldehyde or its derivative on the surfaces of the obtained particles. This composition has a prolonged stable insecticidal effect and is reduced in the toxicity against aquatic animals.
    一种微胶囊杀虫组合物的水悬浮液是在水溶性阴离子聚合物表面活性剂的存在下,通过乳化液体拟除虫菊酯杀虫剂或由拟除虫菊酯杀虫剂和高沸点溶剂(最好是烷基邻苯二甲酸酯,其中烷基有 8 至 13 个碳原子)组成的疏水溶液,以获得具有适当直径的液体颗粒,并在获得的颗粒表面上缩聚三聚氰胺-甲醛或其衍生物而得到的。这种组合物具有长期稳定的杀虫效果,并降低了对水生动物的毒性。
  • Degradation of hydrophobic ester pesticides and toxins
    申请人:Russell Joyce Robyn
    公开号:US20050176117A1
    公开(公告)日:2005-08-11
    The present invention relates to methods and enzymes for degrading hydrophobic ester pesticides and toxins. In particular, the present invention relates to the use of insect esterases, and mutants thereof, in the bioremediation of hydrophobic ester pesticides and toxins residues, such as pyrethroid residues, contaminating the environment and horticultural commodities.
    本发明涉及降解疏水性酯类农药和毒素的方法和酶。特别是,本发明涉及使用昆虫酯酶及其突变体对污染环境和园艺产品的疏水性酯类农药和毒素残留物(如拟除虫菊酯残留物)进行生物修复。
  • DEGRADATION OF HYDROPHOBIC ESTER PESTICIDES AND TOXINS
    申请人:COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
    公开号:EP1478761B1
    公开(公告)日:2012-06-13
  • Methods for Degrading Toxic Compounds
    申请人:Pandey Gunjan
    公开号:US20100279380A1
    公开(公告)日:2010-11-04
    The invention relates to bacteria, bacterial extracts, supernatants obtained from the culturing of said bacteria, polypeptides and compositions for degrading benzimidazole carbamate fungicides, carbanilate fungicides, sulfonamide herbicides, thioamide herbicides and/or synthetic pyrethroid insecticides. In particular, the invention relates to the identification of Nocardioides sp. which degrades benzimidazole carbamate fungicides, carbanilate fungicides, sulfonamide herbicides, thioamide herbicides and/or synthetic pyrethroid insecticides.
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