5-(4-bromo-3,5-dimethylthiophen-2-yl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-[1,2,4]triazole | 503309-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-bromo-3,5-dimethylthiophen-2-yl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-[1,2,4]triazole
• 英文别名: 3-(2-Chloro-6-fluorophenyl)-5-(4-bromo-3,5-dimethylthien-2-yl)-1-methyl-1H-1,2,4-triazole；5-(4-bromo-3,5-dimethylthiophen-2-yl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1,2,4-triazole
• CAS: 503309-09-9
• 化学式: C₁₅H₁₂BrClFN₃S
• 分子量: 400.702
• InChiKey: VPQMMQGPDMZRBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-bromo-3,5-dimethylthiophen-2-yl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-[1,2,4]triazole 、 4-三氟甲氧基苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride sodium carbonate 、 三(邻甲基苯基)磷 作用下， 以 水 、 乙腈 为溶剂， 反应 20.0h， 以26%的产率得到3-(2-chloro-6-fluorophenyl)-1-methyl-5-[3,5-dimethyl-4-(4-trifluoromethoxyphenyl)thiophen-2-yl]-1-methyl-1H-[1,2,4]triazole
  参考文献：
  名称：

  Structure−Activity Relationship Development of Dihaloaryl Triazole Compounds as Insecticides and Acaricides. 1. Phenyl Thiophen-2-yl Triazoles

  摘要：

  An extended lipophilic system that incorporated some key elements of first-gene ration 2,6-dihaloaryl actives, such as 1, demonstrated desirable efficacy against chewing insects as well as sap-feeding insects. These four-ring systems, based on 2, were accessed primarily via Suzuki couplings of halothiophene derivatives with appropriately substituted boronic acids. In particular, phenylthiophene systems that incorporated haloxyether groups, such as those in 3, 4, and 5, had the broadest spectrum of activity across chewing and sap-feeding insect pests. Expansion of this structu re- activity relationship to include compounds with differing substitution patterns on the thiophene-C-ring and aryl-D-rings was undertaken. The synthesis and insecticidal activity of 3-aryl-5-(thiophen-2-yl)-l -methyl1 H-[1,2,4]triazoles will be described.

  DOI：

  10.1021/jf071498s
• 作为产物：
  描述：

  3-(2-chloro-6-fluorophenyl)-1-methyl-5-(4,5-dibromo-3-methyl-thien-2-yl)-1H-1,2,4-triazole 、 碘甲烷 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以47%的产率得到5-(4-bromo-3,5-dimethylthiophen-2-yl)-3-(2-chloro-6-fluorophenyl)-1-methyl-1H-[1,2,4]triazole
  参考文献：
  名称：

  Structure−Activity Relationship Development of Dihaloaryl Triazole Compounds as Insecticides and Acaricides. 1. Phenyl Thiophen-2-yl Triazoles

  摘要：

  An extended lipophilic system that incorporated some key elements of first-gene ration 2,6-dihaloaryl actives, such as 1, demonstrated desirable efficacy against chewing insects as well as sap-feeding insects. These four-ring systems, based on 2, were accessed primarily via Suzuki couplings of halothiophene derivatives with appropriately substituted boronic acids. In particular, phenylthiophene systems that incorporated haloxyether groups, such as those in 3, 4, and 5, had the broadest spectrum of activity across chewing and sap-feeding insect pests. Expansion of this structu re- activity relationship to include compounds with differing substitution patterns on the thiophene-C-ring and aryl-D-rings was undertaken. The synthesis and insecticidal activity of 3-aryl-5-(thiophen-2-yl)-l -methyl1 H-[1,2,4]triazoles will be described.

  DOI：

  10.1021/jf071498s

文献信息

• Insecticial 3-(2,6-disubstituted phenyl)-5-[4- or 5-arylthien-2- or -3-yl]-1,2,4-triazoles
  申请人：——

  公开号：US20030134748A1

  公开（公告）日：2003-07-17

  Triazole compounds having a 2,6-disubstituted-phenyl group in the 3-position, arylthien-2- or -3-yl in the 5-position and an alkyl group in the 1-position are effective in controlling lepidoptera, coleoptera, mites and other sucking pests.

  三唑类化合物，在3位具有2,6-二取代苯基，5位为芳基噻吩-2-或-3-基团，1位为烷基基团，对于控制鳞翅目、鞘翅目、螨类和其他吸食性害虫具有有效性。
• Insecticidal 3-(2,6-disubstituted phenyl)-5-[5-arylthien-3-yl]-1,2,4-triazoles
  申请人：——

  公开号：US20040072887A1

  公开（公告）日：2004-04-15

  Triazole compounds having a 2,6-disubstituted-phenyl group in the 3-position, 5′-arylthien-3-yl group in the 5-position and an alkyl group in the 1-position are effective in controlling lepidoptera, coleoptera, mites and other sucking pests.

  在1-位置具有烷基基团，在3-位置具有2,6-二取代苯基基团，在5-位置具有5'-芳基噻吩-3-基团的三唑类化合物，对于控制鳞翅目、鞘翅目、螨和其他吸食性害虫是有效的。
• Insecticidal 3-(2,6-disubstituted phenyl)-5-[5-arylthien-2-yl]-1,2,4-triazoles
  申请人：——

  公开号：US20040171661A1

  公开（公告）日：2004-09-02

  Triazole compounds having a 2,6-disubstituted-phenyl group in the 3-position, 5′-arylthien-2-yl group in the 5-position and an alkyl group in the 1-position are effective in controlling lepidoptera, coleoptera, mites and other sucking pests.

  在三位上具有2,6-二取代苯基基团，在五位上具有5'-芳基噻吩-2-基基团，在一位上具有烷基基团的三唑类化合物，对控制鳞翅目、鞘翅目、螨类和其他吸食性害虫有效。
• Insecticial 3-(2,6-disubstituted phenyl)-5-[4- or 5-arylthien-2- or -3-yl]-1,2,4-triazoles
  申请人：Dow AgroSciences LLC

  公开号：US06770665B2

  公开（公告）日：2004-08-03

  Triazole compounds having a 2,6-disubstituted-phenyl group in the 3-position, arylthien-2- or -3-yl in the 5-position and an alkyl group in the 1-position are effective in controlling lepidoptera, coleoptera, mites and other sucking pests.

  在三位上具有2,6-二取代苯基基团，在五位上具有芳基噻吩-2-或-3-基团，并在一位上具有烷基基团的三唑类化合物，对于控制鳞翅目、鞘翅目、螨和其他吸食害虫具有有效性。
• INSECTICIDAL 3-(2,6-DISUBSTITUTED PHENYL)-5- 4- OR 5-ARYLTHIEN-2- OR -3-YL|-1,2,4-TRIAZOLES
  申请人：Dow AgroSciences LLC

  公开号：EP1425278B1

  公开（公告）日：2006-12-20