2-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-(methylthiomethyl)-2H-1,2,3-triazole | 129366-61-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-(methylthiomethyl)-2H-1,2,3-triazole
• 英文别名: 2-(2,6-Dichloro-4-trifluoromethylphenyl)-4-(methylthiomethyl)-2H-1,2,3-triazole；2-(2,6-dichloro-4-trifluoro-methylphenyl)-4-(methylthiomethyl)-2H-1,2,3-triazole；2-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-(methylsulfanylmethyl)triazole
• CAS: 129366-61-6
• 化学式: C₁₁H₈Cl₂F₃N₃S
• 分子量: 342.172
• InChiKey: XGDSVYVKZGIDQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-(methylthiomethyl)-2H-1,2,3-triazole 生成
  参考文献：
  名称：

  The Synthesis and Insecticidal Activity of a Series of 2‐Aryl‐1,2,3‐triazoles

  摘要：

  Two synthetic routes to 2-aryl-1,2,3-triazoles are outlined. These have been used to synthesise a wide range of compounds of this structural type. Their insecticidal activities were evaluated against a number of veterinary and public health pests. The activity of these compounds is especially good against the housefly (Musca domestica). Structure-activity relationships are discussed particularly in relation to the physical properties of the compounds.

  DOI：

  10.1002/(sici)1096-9063(199610)48:2<189::aid-ps461>3.0.co;2-#
• 作为产物：
  描述：

  2-(2,6-Dichloro-4-trifluoromethylphenyl)-2H-1,2,3-triazole-4-carbaldehyde 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 异丙醇 、 乙腈 为溶剂， 反应 72.67h， 生成 2-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-(methylthiomethyl)-2H-1,2,3-triazole
  参考文献：
  名称：

  The Synthesis and Insecticidal Activity of a Series of 2‐Aryl‐1,2,3‐triazoles

  摘要：

  Two synthetic routes to 2-aryl-1,2,3-triazoles are outlined. These have been used to synthesise a wide range of compounds of this structural type. Their insecticidal activities were evaluated against a number of veterinary and public health pests. The activity of these compounds is especially good against the housefly (Musca domestica). Structure-activity relationships are discussed particularly in relation to the physical properties of the compounds.

  DOI：

  10.1002/(sici)1096-9063(199610)48:2<189::aid-ps461>3.0.co;2-#

文献信息

• 1,2,3-triazole insecticides
  申请人：Schering Agrochemicals Limited

  公开号：US05064844A1

  公开（公告）日：1991-11-12

  Compounds of formula I ##STR1## and N-oxides thereof, in which Ar is aryl; R.sup.1 and R.sup.2 are the same or different and are hydrogen, alkyl, alkenyl or alkynyl, each of which is optionally substituted, aryl, heterocyclyl, cyano, halogen, nitro, XR.sup.3, S(O).sub.2 NR.sup.4 R.sup.5, CHO and functional derivatives thereof, NR.sup.4 R.sup.5 or CYNR.sup.4 R.sup.5 ; R.sup.3 is hydrogen or optionally substituted alkyl or alkenyl; R.sup.4 and R.sup.5 are the same or different and are hydrogen, optionally substituted alkyl, acyl or aryl, or together with the nitrogen to which they are attached, form a 5 to 7 membered ring which can contain other hetero atoms; X is O, S, S(O).sub.n, OSO.sub.2, YCO or COO; Y is O or S; and n is 1 or 2; have pesticidal activity and especially insecticidal and acaricidal activity. Many of the compounds are novel.

  化学式I的化合物及其N-氧化物，其中Ar是芳基；R.sup.1和R.sup.2相同或不同，可以是氢、烷基、烯基或炔基，每个都可以是可选择取代的芳基、杂环基、氰基、卤素、硝基、XR.sup.3、S(O).sub.2 NR.sup.4 R.sup.5、CHO及其它功能衍生物、NR.sup.4 R.sup.5或CYNR.sup.4 R.sup.5；R.sup.3是氢或可选择取代的烷基或烯基；R.sup.4和R.sup.5相同或不同，可以是氢、可选择取代的烷基、酰基或芳基，或者与它们连接的氮一起形成一个含有其他杂原子的5到7元环；X是O、S、S(O).sub.n、OSO.sub.2、YCO或COO；Y是O或S；n是1或2；具有杀虫活性，尤其是杀虫和杀螨活性。其中许多化合物是新颖的。
• Process for the production of 2-aryl-2H-1,2,3-triazoles
  申请人：Lonza Ltd.

  公开号：US05258523A1

  公开（公告）日：1993-11-02

  4-Akylthiomethyl-2-aryl-2H-1,2,3-triazoles and 4-arylthiomethyl-2-aryl-2H-1,2,3-triazoles are produced from .gamma.-chloroacetoacetyl chloride, aryldiazonium salts and thiolates. In a first step, the aryldiazonium salt is reacted with the chloroacetoacetyl chloride to the corresponding 3-chloropyruvaldehyde-arylhydrazone, which is converted with the thiolate into the corresponding 3-alkylthio or 3-arylthiopyruvaldehyde-arylhydrazone. The 3-alkylthio or 3-arylthiopyruvaldehyde-arylhydrazone is cyclized with hydroxylamine-O-sulfonic acid to the desired 2-aryl-2H-1,2,3-triazole.

  4-烷基硫甲基-2-芳基-2H-1,2,3-三唑和4-芳基硫甲基-2-芳基-2H-1,2,3-三唑是通过γ-氯乙酰氯、芳基重氮盐和硫酸盐制备的。首先，芳基重氮盐与氯乙酰氯反应生成相应的3-氯丙酮醛-芳基腙，然后与硫酸盐转化为相应的3-烷基硫或3-芳基硫丙酮醛-芳基腙。最后，3-烷基硫或3-芳基硫丙酮醛-芳基腙通过羟胺-O-磺酸环化成所需的2-芳基-2H-1,2,3-三唑。
• Triazole insecticides
  申请人：SCHERING AGROCHEMICALS LIMITED

  公开号：EP0350237A2

  公开（公告）日：1990-01-10

  Compounds of formula I and N-oxides thereof, in which Ar is aryl; R¹ and R² are the same or different and are hydrogen, alkyl, alkenyl or alkynyl, each of which is optionally substituted, aryl, heterocyclyl, cyano, halogen, nitro, XR³, S(O)₂NR⁴R⁵, CHO and functional derivatives thereof, NR⁴R⁵ or CYNR⁴R⁵; R³ is hydrogen or optionally substituted alkyl or alkenyl; R⁴ and R⁵ are the same or different and are hydrogen, optionally substituted alkyl, acyl or aryl, or together with the nitrogen to which they are attached, form a 5 to 7 membered ring which can contain other hetero atoms; X is O, S, S(O)n, OSO₂, YCO or COO; Y is O or S; and n is 1 or 2; have pesticidal activity and especially insecticidal and acaricidal activity. Many of the compounds are novel.

  式 I 的化合物 及其 N-氧化物，其中 Ar 是芳基； R¹ 和 R² 是相同或不同的，并且是氢、烷基、烯基或炔基（其中每个都是任选取代的）、芳基、杂环基、氰基、卤素、硝基、XR³、S(O)₂NR⁴R⁵、CHO 及其官能衍生物、NR⁴R⁵ 或 CYNR⁴R⁵； R³ 是氢或任选取代的烷基或烯基； R⁴和 R⁵ 可以相同或不同，并且是氢、任选取代的烷基、酰基或芳基，或与它们所连接的氮一起形成可包含其他杂原子的 5 至 7 个成员的环； X 是 O、S、S(O)n、OSO₂、YCO 或 COO； Y 是 O 或 S；n 是 1 或 2；具有杀虫活性，尤其是杀虫和杀螨剂活性。许多化合物都是新颖的。
• Verfahren zur Herstellung von 2-Aryl-2H-1,2,3-triazolen
  申请人：LONZA AG

  公开号：EP0527314A1

  公开（公告）日：1993-02-17

  4-Alkylthiomethyl-2-aryl-2H-1,2,3-triazole und 4-Arylthiomethyl-2-aryl-2H-1,2,3-triazole werden aus γ-Chloracetoacetylchlorid, Aryldiazoniumsalzen und Thiolaten hergestellt. In einer ersten Stufe wird das Aryldiazoniumsalz mit dem γ-Chloracetoacetylchlorid zu dem entsprechenden 3-Chlorpyruvaldehyd-arylhydrazon umgesetzt, welches mit dem Thiolat in das entsprechende 3-Alkylthio- bzw. 3-Arylthiopyruvaldehydarylhydrazon übergeführt wird. Das 3-Alkylthio- bzw. 3-Arylthiopyruvaldehyd-arylhydrazon wird mit Hydroxylamin-O-sulfonsäure zu dem gewünschten 2-Aryl-2H-1,2,3-triazol cyclisiert.

  4- 烷基硫甲基-2-芳基-2H-1,2,3-三唑和 4- 芳基硫甲基-2-芳基-2H-1,2,3-三唑由 γ-氯乙酰氯、芳基重氮盐和硫醇盐制备。第一步，芳基重氮盐与 γ-氯代乙酰氯反应生成相应的 3-氯代丙酮醛芳基腙，再与硫醇酸盐反应生成相应的 3-烷硫基或 3-芳基硫代丙酮醛芳基腙。 3-alkylthio- 或 3-arylthiopyruvaldehyde 芳醛腙与羟胺-O-磺酸环化成所需的 2-芳基-2H-1,2,3-三唑。
• US5064844A
  申请人：——

  公开号：US5064844A

  公开（公告）日：1991-11-12