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trans-5-(4-Chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-3-thiazolidinecarboxamide | 78587-05-0

中文名称
——
中文别名
——
英文名称
trans-5-(4-Chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-3-thiazolidinecarboxamide
英文别名
(4R,5R)-5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide
trans-5-(4-Chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-3-thiazolidinecarboxamide化学式
CAS
78587-05-0
化学式
C17H21ClN2O2S
mdl
——
分子量
352.9
InChiKey
XGWIJUOSCAQSSV-ABAIWWIYSA-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

物化性质

  • 熔点:
    108-108.5°C
  • 沸点:
    128°C (rough estimate)
  • 密度:
    1.1354 (rough estimate)
  • 闪点:
    100 °C
  • 溶解度:
    DMF: 5 mg/ml,DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml,DMSO: 2 mg/ml,乙醇: 0.2 mg/ml
  • 颜色/状态:
    White crystals
  • 气味:
    Odorless
  • 蒸汽压力:
    2.55X10-8 mm Hg at 20 °C
  • 稳定性/保质期:
    Stable under recommended storage conditions.
  • 分解:
    When heated to decomposition it emits toxic vapors of /nitrogen oxides, sulfur oxides, and chloride//

计算性质

  • 辛醇/水分配系数(LogP):
    4.5
  • 重原子数:
    23
  • 可旋转键数:
    2
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.53
  • 拓扑面积:
    74.7
  • 氢给体数:
    1
  • 氢受体数:
    3

ADMET

代谢
三组各五只雄性和五只雌性的Fischer F344大鼠(10周龄)被给予单次口服剂量的[噻唑啉-5-(14)C]己噻唑氧(比活度,6.6 mCi/mmol;纯度,> 99%)。三种不同的处理方案包括单次口服低剂量(10 mg/kg bw)、在十四次口服未标记己噻唑氧后单次口服低剂量以及单次口服高剂量(880 mg/kg bw)。低剂量相当于大约50 uCi/kg bw,高剂量大约为90 uCi/kg bw。低剂量的溶剂选择为二甲亚砜(DMSO),而高剂量的溶剂选择为橄榄油,因为己噻唑氧在DMSO中的溶解度有限。...来自这些研究的样本...被提取并分析代谢物。在低剂量组中,主要识别出的化合物是己噻唑氧,在尿液中的放射性约为给药放射性的2%,在粪便中约为40%。提取到甲醇中的未识别化合物在尿液中的放射性约占80%,在粪便中的放射性约占30%。主要识别出的代谢反应是环己烷环的羟基化和酰胺-环己烷键的断裂。在低剂量组中,排泄物中主要识别出的放射性标记代谢物是PT-1-8(顺式),占给药放射性的8-12%。其余识别出的代谢物浓度较低(每个都小于给药放射性的2%):PT-1-2、PT-1-3、PT-1-4、PT-1-8(反式)、PT-1-9、PT-1-10和PC-1-1。脂肪中主要识别出的放射性标记成分是母化合物;在肝脏和肾脏中,主要的代谢物是PT-1-4。
Three groups of five male and five female Fischer F344 rats (age 10 weeks) rats were given a single oral dose of [thiazolidine-5-(14)C]hexythiazox (specific activity, 6.6 mCi/mmol; purity, > 99%). The three different treatment protocols included a single oral dose at a lower dose (10 mg/kg bw), a single oral dose at the lower dose after fourteen oral doses of unlabeled hexythiazox and a single oral dose at a higher dose (880 mg/kg bw). The lower dose equated to approximately 50 uCi/kg bw and the higher dose, approximately 90 uCi/kg bw. The vehicle chosen for administration of the lower dosedimethyl sulfoxide (DMSO), while the vehicle chosen for the higher dose was olive oil, because of the solubility limitations of hexythiazox in DMSO. ... Samples from /these/ studies ... were extracted and analyzed for metabolites. In the groups at the lower dose, the primary identified compound was hexythiazox, present in the urine at approximately 2% of the administered radioactivity and in feces at approximately 40% of the administered radioactivity. Unidentified compounds extracting into methanol represented approximately 80% of the radioactivity in urine and 30% of the fecal radioactivity. The primary, identified metabolic reactions were hydroxylation of the cyclohexane ring and cleavage of the amide-cyclohexane bond. The major identified radiolabelled metabolite in excreta was PT-1-8 (cis), which comprised 8-12% of the administered radioactivity in excreta in the groups at the lower dose. The remaining identified metabolites were present at low concentrations (each < 2% of the administered radioactivity): PT-1-2, PT-1-3, PT-1-4, PT-1-8 (trans), PT-1-9, PT-1-10 and PC-1-1. The major identified radiolabelled component in fat was the parent compound; the predominant metabolite in liver and kidney was PT-1-4.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 毒性总结
识别和使用:Hexythiazox 是一种固体。Hexythiazox 是一种杀螨剂,对卵、幼虫和若虫阶段起作用。人类暴露和毒性:在流行病学报告中,Hexythiazox 没有与不良反应联系在一起。菲律宾曾报道过一起中毒事件。动物研究:Hexythiazox 对兔子的皮肤无刺激性;对眼睛有轻微、暂时刺激性,并且在最大程度测试中没有显示出皮肤致敏潜力。大鼠90天喂养研究显示,两个性别的肝脏重量增加;在500和3500 ppm时,相对卵巢和雌性肾脏重量增加;在500 ppm喂养2个月后,血液总蛋白和白蛋白水平增加;在500和3500 ppm时,两个性别的肾上腺皮质的带状区域出现脂肪变性。在接受Hexythiazox的大鼠和对照组中,肿瘤发生率(良性和恶性)总体相似。兔子和大鼠的发育研究没有表明Hexythiazox有任何致畸潜力。Hexythiazox 已经在一系列的试验中测试了其基因毒性。证据的权重是Hexythiazox没有显著的基因毒性潜力。生态毒性研究:Hexythiazox 对鸟类在急性基础上几乎无毒。鹌鹑的急性LD50大于2510 mg/kg,而绿头鸭和鹌鹑的LC50大于5620 ppm。然而,没有审查鸟类的繁殖研究。Hexythiazox 对小哺乳动物也几乎无毒(LD50 >5000 mg/kg,繁殖NOAEL >/= 2400 ppm 实验大鼠,急性和两代)。Hexythiazox 对淡水物种具有急性高毒性。蓝鳃鱼的LC50为0.53 ppm,水蚤的EC50为0.74 ppm。在补充的慢性生命周期测试中,接触技术级的Hexythiazox 对水蚤的存活产生了不利影响(NOAEC = 6.1 ppb 和 LOAEC = 12.7 ppb)。
IDENTIFICATION AND USE: Hexythiazox is a solid. Hexythiazox is an acaricide that acts against egg, larval and nymph stages. HUMAN EXPOSURE AND TOXICITY: Hexythiazox has not been linked to adverse effects in any epidemiological reports. A single poisoning incident has been reported in the Philippines. ANIMAL STUDIES: Hexythiazox was not irritating to the skin of rabbits; was a slight, transient eye irritant and produced no evidence of skin sensitizing potential in maximization tests. 90-day feeding study in rats demonstrated increased liver weights in both sexes; increased relative ovary and female kidney weights at 500 and 3500 ppm; increased blood total protein and albumin levels at 500 ppm after 2-months of feeding; fatty degeneration of the zona fasciculta of the adrenal cortex of both sexes at 500 and 3500 ppm. Overall rates of tumor incidence (benign and malignant) were similar in rats receiving hexythiazox and in the control group. Developmental studies in rabbits and rats did not indicate any teratogenic potential for hexythiazox. Hexythiazox has been tested for genotoxicity in a wide range of assays. The weight of evidence is that hexythiazox has no significant genotoxic potential. ECOTOXICITY STUDIES: Hexythiazox is practically nontoxic to birds on an acute basis. The bobwhite acute LD50 is >2,510 mg/Kg while the mallard and bobwhite LC50's were >5,620 ppm. However, no avian reproduction studies were reviewed. Hexythiazox is also practically nontoxic to small mammals (LD50 >5000 mg/kg, reproductive NOAEL >/= 2400 ppm laboratory rat, acute and two generation). Hexythiazox is acutely highly toxic to freshwater species. The LC50 for bluegill is 0.53 ppm and the EC50 for Daphnia is 0.74 ppm. In a supplemental chronic life-cycle test, exposure to technical hexythiazox adversely affected survival in daphnia (NOAEC = 6.1 ppb and LOAEC = 12.7 ppb).
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌性证据
癌症分类:C组可能的人类致癌物
Cancer Classification: Group C Possible Human Carcinogen
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 副作用
职业性肝毒素 - 第二性肝毒素:在职业环境中的毒性效应潜力是基于人类摄入或动物实验的中毒病例。
Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
毒理性
  • 毒性数据
大鼠 LC50 > 2000 mg/m³
LC50 (rat) > 2,000 mg/m3
来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
毒理性
  • 解毒与急救
/SRP:/ 立即急救:确保已经进行了充分的中和。如果患者停止呼吸,请开始人工呼吸,最好使用需求阀复苏器、球囊阀面罩设备或口袋面罩,按训练操作。如有必要,执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果患者呕吐,让患者向前倾或将其置于左侧(如果可能的话,头部向下)以保持呼吸道畅通,防止吸入。保持患者安静,维持正常体温。寻求医疗救助。 /毒物A和B/
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
三组每组五只雄性和五只雌性Fischer F344大鼠(10周龄)口服单一剂量的[噻唑啉-5-(14)C]己噻唑氧(比活性,6.6 mCi/mmol;纯度,> 99%)。三种不同的处理方案包括:低剂量(10 mg/kg体重)单次口服给药、在连续口服十四次未标记己噻唑氧后低剂量单次口服给药、以及高剂量(880 mg/kg体重)单次口服给药。低剂量相当于大约50 uCi/kg体重,高剂量大约为90 uCi/kg体重。低剂量给药时选择的溶剂是二甲亚砜(DMSO),而高剂量给药时选择的溶剂是橄榄油,因为己噻唑氧在DMSO中的溶解度有限。... 在10 mg/kg体重组(B组和C组)给药后大约3-4小时观察到血浆中放射性活性的最大浓度,而在880 mg/kg体重组(D组)给药后12小时观察到。在那些时间点,B组和C组雄性大鼠的平均血浆放射性活性浓度为1.8-2.2 ppm,雌性大鼠为2.3-2.6 ppm,D组雄性大鼠为37 ppm,雌性大鼠为27 ppm;表明在高剂量时吸收达到饱和。在给药后72或96小时,B组和C组大鼠的血浆中大约还有0.1 ppm的放射性活性;D组的血浆中放射性活性浓度已降至大约2 ppm。血浆的吸收和消除遵循一级动力学,10 mg/kg体重雄性大鼠的速率常数分别为0.53/小时和大约0.075/小时。消除速率常数对应的半衰期大约为9小时。在雌性大鼠中,半衰期略长,为11.4小时,而在高剂量时,雄性和雌性大鼠的半衰期分别延长至17.3小时和21.7小时。在B组和C组中,大约30%的放射性活性通过尿液排出,大约60-70%的放射性活性在粪便中回收。在D组中,9.5%的放射性活性在尿液中,89.1%在粪便中。在96小时时,与组织相关的给药剂量为1.1-10.1%。放射性活性的最高浓度出现在脂肪、肾上腺、肝脏、卵巢和消化器官及其内容物中。在给药后96小时,脂肪组织中放射性活性的最高浓度分别达到大约2.3、1.2和76 ppm(雄性)以及5.4、3.3和129 ppm(雌性),分别对应于B组、C组和D组。在肝脏中大约有36-71%的放射性活性在提取后仍以结合态存在,而在脂肪中少于2%的放射性活性以结合态存在。脂肪中的残留浓度在雌性大鼠中通常是雄性大鼠的两倍。在研究结束时脂肪中的放射性活性浓度较低,但仍是血浆中的20多倍,表明有一定的生物积累潜力。在雄性和雌性大鼠之间或重复给药后的吸收和排泄模式没有显著差异。
Three groups of five male and five female Fischer F344 rats (age 10 weeks) rats were given a single oral dose of [thiazolidine-5-(14)C]hexythiazox (specific activity, 6.6 mCi/mmol; purity, > 99%). The three different treatment protocols included a single oral dose at a lower dose (10 mg/kg bw), a single oral dose at the lower dose after fourteen oral doses of unlabeled hexythiazox and a single oral dose at a higher dose (880 mg/kg bw). The lower dose equated to approximately 50 uCi/kg bw and the higher dose, approximately 90 uCi/kg bw. The vehicle chosen for administration of the lower dose was dimethyl sulfoxide (DMSO), while the vehicle chosen for the higher dose was olive oil, because of the solubility limitations of hexythiazox in DMSO. ... The maximum concentrations of radioactivity in plasma were observed about 3-4 hr after administration in the groups at 10 mg/kg bw groups (groups B & C) and 12 hr after dosing at at 880 mg/kg bw (group D). At those times the mean plasma concentrations of radioactivity in groups B and C were 1.8-2.2 ppm for males and 2.3-2.6 ppm for females, and in group D, 37 ppm for males and 27 ppm for females; indicating saturation of absorption at the higher dose. At 72 or 96 hr after administration approximately 0.1 ppm of the radioactivity remained in the plasma in groups B and C; the concentrations of radioactivity in plasma in group D had decreased to approximately 2 ppm. The plasma absorption and elimination followed first-order kinetics, with rate constants of 0.53/hr and approximately 0.075/hr respectively, at 10 mg/kg bw in males. The elimination rate constant corresponded to a half-life of approximately 9 hr. In females, the half-life was slightly longer at 11.4 hr and the half-life was also prolonged in males and females at the higher dose, at 17.3 and 21.7 hr, respectively. In groups B and C approximately 30% of the administered radioactivity was excreted in the urine and approximately 60-70% of the administered radioactivity was recovered in the feces. In group D, 9.5% of the radioactivity was found in the urine and 89.1% in the feces. Of the administered dose, 1.1-10.1% was associated with tissues at 96 hr. The highest concentrations of radioactivity were found in fat, adrenal, liver, ovary and digestive organs and their contents. The highest concentrations of radioactivity in tissues were observed in fat 96 hr after dosing, reaching approximately 2.3, 1.2 and 76 ppm in males and 5.4, 3.3 and 129 ppm in females, in groups B, C and D, respectively. Approximately 36-71% of the radioactivity in the liver and less than 2% of the radioactivity in fat remained as bound (14)C after extraction. Residue concentrations in fat were generally twice as high in females as in males. Concentrations of radioactivity in fat at the end of the studies were low, but more than 20-fold those in plasma, indicating some potential for bioaccumulation. There were no remarkable differences in patterns of absorption and excretory patterns between males and females or after repeated doses.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 危险品标志:
    N
  • 安全说明:
    S60,S61
  • 危险类别码:
    R50/53
  • WGK Germany:
    2
  • 海关编码:
    2934100011
  • 危险品运输编号:
    UN 3077
  • RTECS号:
    XJ5396000

SDS

SDS:051a6d9ce50102d15485bf2d719a6342
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制备方法与用途

根据提供的信息,这里总结了关于噻螨酮的生产方法:

  1. 关键中间体反式5-(4-氯苯基)-4-甲基-2-氧代噻唑烷酮:

    • 由赤-2-氨基-1-对氯苯基丙醇硫酸酯在乙醇中与二硫化碳环合氧化得到
    • 或一步法直接从赤-2-氨基-1-对氯苯基丙醇硫酸酯和过量氧硫化碳反应制得
  2. 环己基异氰酸酯:

    • 可由环己胺与二氧化碳、四氯化硅/三甲基氯化硅合成
    • 或用环己胺盐酸盐和光气反应制备
    • 也可通过环己胺和一氧化碳在催化剂作用下加压反应得到
  3. 噻螨酮最终产物:

    • 将反式噻唑烷酮与环己基异氰酸酯在溶剂中缩合制得
    • 或使用强碱性催化剂1,8-二氮双环-5,4-十一碳-7-烯

总的来说,生产方法主要涉及环合、氧化反应和缩合等步骤。该工艺路线合理简洁,各步转化率较高。

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

点击查看最新优质反应信息

文献信息

  • N-Formyl phosphonamidothioates
    申请人:E.I. DU PONT DE NEMOURS AND COMPANY
    公开号:EP0322195A1
    公开(公告)日:1989-06-28
    This invention relates to certain N-formyl phosphonamidothioates, agriculturally suitable compositions containing them, and their use as insecticides, acaricides and nematocides.
    这项发明涉及某些N-甲酰磷酰氨基硫酸酯,含有它们的农业适用组合物,以及它们作为杀虫剂、杀螨剂和杀线虫剂的用途。
  • Insecticidal and acaricidal phenoxypyridinyl esters and intermediates
    申请人:E.I. DU PONT DE NEMOURS AND COMPANY
    公开号:EP0223521A2
    公开(公告)日:1987-05-27
    Compounds of the formula wherein R is a substituted cyclopropane ring of defined structure; X is 0 or S n is 1 to 3 m is 0 or 1 R, is H, halogen or various organic groups; R2 is H, halogen, CH3 or CF3; exhibit insecticidal and acaricidal activity. Some are active in soil. The compounds may be made by esterifying the appropriate cyclopropanecarboxylic acid with the appropriate 1-pyridyl-2,2,2-trifluoroethanol also novel per se.
    式中的化合物 其中 R 是定义结构的取代环丙烷环; X 是 0 或 S n 为 1 至 3 m 为 0 或 1 R 是 H、卤素或各种有机基团; R2 是 H、卤素、CH3 或 CF3; 具有杀虫和杀螨活性。有些在土壤中具有活性。 这些化合物可通过将适当的环丙烷羧酸与适当的 1-吡啶基-2,2,2-三氟乙醇酯化制成,这本身也是一种新颖的化合物。
  • Insecticidal substituted indazoles
    申请人:E.I. DU PONT DE NEMOURS AND COMPANY
    公开号:EP0286346A2
    公开(公告)日:1988-10-12
    Compounds to the formula wherein Q is A is an optionally substituted 1,2 or 3-atom bridge having 0 to 3 carbon atoms and 0 to 1 oxygen atom. NR6 or S(O)q group; B is H or an organic group; J is H, alkyl or phenyl; K is H or CH3; R1 and R2 are organic or inorganic substituents; X is 0 or S; Y is H or an organic substituent; exhibit insecticidal activity and may be utilised for plant protection.
    式中的化合物 式中 Q 是 A 是具有 0 至 3 个碳原子和 0 至 1 个氧原子的任选取代的 1、2 或 3 个原子桥。NR6 或 S(O)q 基团; B 是 H 或有机基团 J 是 H、烷基或苯基 K 是 H 或 CH3; R1 和 R2 是有机或无机取代基; X 是 0 或 S; Y 是 H 或有机取代基; 具有杀虫活性,可用于植物保护。
  • Insecticidal pyrazolines
    申请人:E.I. DU PONT DE NEMOURS AND COMPANY
    公开号:EP0300692A1
    公开(公告)日:1989-01-25
    Pyrazoline derivatives of the formula: wherein R₁, R₂ and R₃ are independently selected from hydrogen or defined organic or inorganic substituents, R₅ is a carboxylic acid, ester or amide substituent, or a sulfonamide group; R₆ and R₇ are H or alkyl; m, n and p are zero or integers; X is O or S; Y is H or an organic substituent; exhibit activity against a wide spectrum of foliar and soil inhabiting insects, and hence may be used for crop protection.
    式中的吡唑啉衍生物: 其中 R₁、R₂ 和 R₃ 独立选自氢或定义的有机或无机取代基、 R₅ 是羧酸、酯或酰胺取代基,或磺酰胺基; R₆ 和 R₇ 是 H 或烷基; m、n 和 p 为零或整数; X 是 O 或 S Y 是 H 或有机取代基; 对多种叶面和土壤中栖息的昆虫具有活性,因此可用于作物保护。
  • Heterocyclic pyrazoline carboxanilides
    申请人:E.I. DU PONT DE NEMOURS AND COMPANY
    公开号:EP0322126A1
    公开(公告)日:1989-06-28
    Heterocyclic pyrazoline carboxanilide insecticides of the general formula: including all geometric and stereoisomers thereof, as well as agricultural compositions containing them.
    通式如下的杂环吡唑啉羧酰苯胺杀虫剂: 包括其所有几何异构体和立体异构体,以及含有它们的农用组合物。
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