3-Ethyl-5-methyl-4-aminophenol | 112730-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-Ethyl-5-methyl-4-aminophenol
• 英文别名: 4-amino-3-ethyl-5-methylphenol；2-ethyl-4-hydroxy-6-methylaniline；3-ethyl-4-amino-5-methylphenol
• CAS: 112730-54-8
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: PNPYYSANMRPVKP-UHFFFAOYSA-N

物化性质

• 沸点：
  310.1±30.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Ethyl-5-methyl-4-aminophenol 在 lead(IV) acetate 作用下， 以 乙酸乙酯 为溶剂， 反应 0.17h， 生成 3-乙基-4-亚氨基-5-甲基-2,5-环己二烯-1-酮
  参考文献：
  名称：

  Dialkylquinoneimine metabolites of chloroacetanilide herbicides induce sister chromatid exchanges in cultured human lymphocytes

  摘要：

  Some of the most widely-used herbicides are the chloroacetanilides exemplified by alachlor and butachlor (derived from 2,6-diethylaniline) and metolachlor and acetochlor (synthesized from 2-ethyl-6-methyIaniline). This investigation tests the hypothesis that the previously-observed oncogenicity of these herbicides is due to genotoxic intermediates such as diethylbenzoquinoneimine, a purported alachlor metabolite. Syntheses are reported here for the corresponding 2,6-dialkylbenzoquinoneimines, selected chloroacetyldialkylbenzoquinoneimines and several other candidate or known metabolites. The possible mutagenicity of diethylbenzoquinoneimine was tested in Salmonella typhimurium strains TA98 and TA100 with a weakly-positive response in the TA100 strain indicating induction of base-pair substitution mutations. The frequency of sister chromatid exchange (SCE) in Chinese hamster ovary cells was increased by alachlor at 10 mu M and diethylaniline but not ethylmethylaniline at 30 and 3 mu M Isolated and cultured peripheral lymphocytes (mostly T cells) were used from two human donors to study the effects of the chloroacetanilides and their metabolites on primary human cells. In tests at 10 mu M, the SCE frequency was increased by alachlor and possibly acetochlor but not by butachlor, metolachlor, dimethachlor (a 2,6-dimethyl analog) and dimethenamid (an analog based on 2,4-dimethyl-3 -thienylamine). At 0.3 mu M in cultured human lymphocytes, alachlor, the corresponding chloroacetanilide( N-dealkyl-alachlor) and aniline metabolites (and their 4-hydroxy derivatives), and diethylbenzoquinone were inactive or active in only one of the two donors whereas at 0.1-0.3 mu M the SCE ratio for treated cells divided by the controls was always higher for diethylbenzoquinoneimine than for ethylmethyl- and dimethylbenzoquinoneimines. All the tested compounds were toxic to lymphocytes, but the depression of the mitotic index and increased duration of the cell cycle were not directly linked with SCE induction. Previous investigations have suggested that chloroacetanilide herbicides such as alachlor derived from 2,6-dialkylanilines are metabolized to 2,6-dialkylbenzoquinoneimines and the present study provides the first direct evidence that these metabolites are genotoxic in human lymphocytes. (C) 1997 Elsevier Science B.V.

  DOI：

  10.1016/s1383-5718(97)00163-0
• 作为产物：
  描述：

  3-甲基-5-乙基苯酚 在 sodium dithionite 作用下， 生成 3-Ethyl-5-methyl-4-aminophenol
  参考文献：
  名称：

  Dialkylquinoneimine metabolites of chloroacetanilide herbicides induce sister chromatid exchanges in cultured human lymphocytes

  摘要：

  Some of the most widely-used herbicides are the chloroacetanilides exemplified by alachlor and butachlor (derived from 2,6-diethylaniline) and metolachlor and acetochlor (synthesized from 2-ethyl-6-methyIaniline). This investigation tests the hypothesis that the previously-observed oncogenicity of these herbicides is due to genotoxic intermediates such as diethylbenzoquinoneimine, a purported alachlor metabolite. Syntheses are reported here for the corresponding 2,6-dialkylbenzoquinoneimines, selected chloroacetyldialkylbenzoquinoneimines and several other candidate or known metabolites. The possible mutagenicity of diethylbenzoquinoneimine was tested in Salmonella typhimurium strains TA98 and TA100 with a weakly-positive response in the TA100 strain indicating induction of base-pair substitution mutations. The frequency of sister chromatid exchange (SCE) in Chinese hamster ovary cells was increased by alachlor at 10 mu M and diethylaniline but not ethylmethylaniline at 30 and 3 mu M Isolated and cultured peripheral lymphocytes (mostly T cells) were used from two human donors to study the effects of the chloroacetanilides and their metabolites on primary human cells. In tests at 10 mu M, the SCE frequency was increased by alachlor and possibly acetochlor but not by butachlor, metolachlor, dimethachlor (a 2,6-dimethyl analog) and dimethenamid (an analog based on 2,4-dimethyl-3 -thienylamine). At 0.3 mu M in cultured human lymphocytes, alachlor, the corresponding chloroacetanilide( N-dealkyl-alachlor) and aniline metabolites (and their 4-hydroxy derivatives), and diethylbenzoquinone were inactive or active in only one of the two donors whereas at 0.1-0.3 mu M the SCE ratio for treated cells divided by the controls was always higher for diethylbenzoquinoneimine than for ethylmethyl- and dimethylbenzoquinoneimines. All the tested compounds were toxic to lymphocytes, but the depression of the mitotic index and increased duration of the cell cycle were not directly linked with SCE induction. Previous investigations have suggested that chloroacetanilide herbicides such as alachlor derived from 2,6-dialkylanilines are metabolized to 2,6-dialkylbenzoquinoneimines and the present study provides the first direct evidence that these metabolites are genotoxic in human lymphocytes. (C) 1997 Elsevier Science B.V.

  DOI：

  10.1016/s1383-5718(97)00163-0

文献信息

• N-pyridyloxyphenylisothioureas and the use thereof in pest control
  申请人：Ciba-Geigy Corporation

  公开号：US04866079A1

  公开（公告）日：1989-09-12

  The invention relates to novel N-pyridyloxyphenylisothioureas of formula I ##STR1## wherein the substituents R.sub.1 are each independently halogen, C.sub.1 -C.sub.3 alkyl, a mono- or polyhalogenated C.sub.1 -C.sub.3 alkyl group, or --COOR.sub.7 ; R.sub.2, R.sub.3 and R.sub.7 are each independently C.sub.1 -C.sub.5 alkyl, with the proviso that R.sub.2 and R.sub.3 are not simultaneously methyl if R.sub.6 is tert-butyl and the substituents R.sub.1 are chlorine and/or trifluoromethyl; R.sub.4 is hydrogen or methyl; R.sub.5 is C.sub.1 -C.sub.6 alkyl; R.sub.6 is C.sub.1 -C.sub.12 alkyl, a mono- or polyhalogenated C.sub.1 -C.sub.12 alkyl group, C.sub.1 -C.sub.6 alkoxy-C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 cycloalkyl, a mono- or di(C.sub.1 -C.sub.3)alkylated C.sub.3 -C.sub.8 cycloalkyl group, C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 -alkyl, or a polycyclic alkyl radical containing 7 to 10 carbon atoms; and n is 0 to 4; to their salts with organic or inorganic acids, to the preparation thereof, to their use in pest control, as well as to pesticidal compositions which contain at least one compound of formula I or an active intermediate. The preferred area of application is the control of pests of animals and plants.

  该发明涉及新型的N-吡啶氧基苯基异硫脲，其化学式为I 其中取代基R.sub.1分别为卤素、C.sub.1 -C.sub.3烷基、单取代或多卤代的C.sub.1 -C.sub.3烷基，或--COOR.sub.7；R.sub.2、R.sub.3和R.sub.7分别为C.sub.1 -C.sub.5烷基，但要求当R.sub.6为叔丁基并且取代基R.sub.1为氯和/或三氟甲基时，R.sub.2和R.sub.3不能同时为甲基；R.sub.4为氢或甲基；R.sub.5为C.sub.1 -C.sub.6烷基；R.sub.6为C.sub.1 -C.sub.12烷基、单取代或多卤代的C.sub.1 -C.sub.12烷基，C.sub.1 -C.sub.6烷氧基-C.sub.1 -C.sub.12烷基，C.sub.3 -C.sub.8环烷基，单取代或二(C.sub.1 -C.sub.3)烷基化的C.sub.3 -C.sub.8环烷基，C.sub.3 -C.sub.8环烷基-C.sub.1 -C.sub.4-烷基，或者含有7到10个碳原子的多环烷基基团；n为0至4；其与有机或无机酸的盐，其制备方法，其在害虫控制中的用途，以及至少含有化合物I或活性中间体的杀虫剂组合物。首选的应用领域是动植物害虫的控制。
• Immunological detection of metolachlor
  申请人：Ciba-Geigy Corporation

  公开号：US05576188A1

  公开（公告）日：1996-11-19

  The present invention relates to monoclonal antibodies which are distinguished by high selectivity and affinity for metolachlor and which are therefore outstandingly suitable for use in an immunoassay for the rapid and efficient detection of metolachlor. Another aspect of the present invention relates to hybridoma cell lines which produce said monoclonal antibodies and to immunological methods for detecting metolachlor in samples of soil, water or air using said monoclonal antibodies and to the test kits which can be used within the scope of these detection methods.

  本发明涉及单克隆抗体，其具有高选择性和亲和力，因此非常适用于用于快速和有效检测甲胺磷的免疫测定。本发明的另一个方面涉及产生所述单克隆抗体的杂交瘤细胞系，以及使用所述单克隆抗体在土壤、水或空气样品中检测甲胺磷的免疫学方法，以及可在这些检测方法范围内使用的测试工具包。
• N-Pyridyloxyphenyl-isothioharnstoffe, ihre Herstellung und Verwendung bei der Kontrolle von Schädlingen
  申请人：CIBA-GEIGY AG

  公开号：EP0239535A2

  公开（公告）日：1987-09-30

  Neue N-Pyridyloxyphenyl-isothioharnstoffe der Formel I worin R₁ je für Halogen, C₁-C₃-Alkyl, ein ein- oder mehrfach halogenier­tes C₁-C₃-Alkyl oder -COOR₇, R₂ R₃ und R₇ je für C₁-C₅-Alkyl, mit der Massgabe, dass R₂ und R₃ nicht gleichzeitig Methyl bedeuten, wenn R₆ tert.Butyl und R₁ Chlor und/oder Trifluormethyl sind, R₄ für Wasserstoff oder Methyl, R₅ für C₁-C₆-Alkyl, R₆ für C₁-C₁₂-Alkyl, ein ein- oder mehrfach halogeniertes C₁-C₁₂-­Alkyl, C₁-C₆-Alkoxy-C₁-C₁₂-alkyl, C₃-C₈-Cycloalkyl, ein ein- oder zweifach C₁-C₃-alkyliertes C₃-C₈-Cycloalkyl, C₃-C₈-Cyclo­alkyl-C₁-C₄-alkyl oder einen polycyclischen Alkylrest mit 7 bis 10 C-Atomen und n für eine Zahl von 0 bis 4 stehen, und ihre Salze mit organischen oder anorganischen Säuren, Verfahren zu ihrer Herstellung, ihre Verwendung in der Schädlings­bekämpfung, sowie Schädlingsbekämpfungsmittel, welche mindestens eine Verbindung der Formel I oder ein aktives Zwischenprodukt enthalten, werden offenbart. Bevorzugtes Anwendungsgebiet ist die Bekämpfung von Schädlingen an Tieren und Pflanzen.

  式 I 的新型 N-吡啶氧基苯基-异硫脲 其中 R₁ 各自代表卤素、C₁-C₃-烷基、单卤代或多卤代 C₁-C₃ 烷基或 -COOR₇、 R₂ R₃ 和 R₇ 各为 C₁-C₅ 烷基，但如果 R₆ 为叔丁基且 R₁ 为氯和/或三氟甲基，则 R₂ 和 R₃ 不能同时为甲基、 R₄ 为氢或甲基、 R₅为C₁-C₆-烷基、 R₆代表 C₁-C₁₂-烷基、单卤代或多卤代 C₁-C₁₂-烷基、C₁-C₆-烷氧基-C₁-C₁₂-烷基、C₃-C₈-环烷基、C₃-C₈-环烷基、C₃-C₈-环烷基-C₁-C₄-烷基或具有 7 至 10 个碳原子的多环烷基的单-或双-C₁-C₃-烷基，以及 n 是 0 至 4 的数字 及其与有机酸或无机酸的盐、其制备工艺、其在害虫防治中的用途以及含有至少一种式 I 化合物或活性中间体的杀虫剂均已公开。首选的应用领域是防治动物和植物上的害虫。
• Immunologischer Nachweis von Metolachlor
  申请人：Novartis AG

  公开号：EP0446173B1

  公开（公告）日：1999-07-14
• US4059567A
  申请人：——

  公开号：US4059567A

  公开（公告）日：1977-11-22