2-硫杂氮醇胺,N-(4-氯-2-甲基苯基)-4,5-二氢- | 110470-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-硫杂氮醇胺,N-(4-氯-2-甲基苯基)-4,5-二氢-
• 英文名称: 2-(4-chloro-o-toluidino)-2-thiazoline
• 英文别名: N-(4-Chloro-2-methylphenyl)-4,5-dihydro-2-thiazolamine；N-(4-chloro-2-methylphenyl)-4,5-dihydro-1,3-thiazol-2-amine
• CAS: 110470-64-9
• 化学式: C₁₀H₁₁ClN₂S
• 分子量: 226.73
• InChiKey: GTAYXLDODNXXPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride 、 2-硫杂氮醇胺,N-(4-氯-2-甲基苯基)-4,5-二氢- 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 5-bromo-N-(4-chloro-2-methylphenyl)-2-(3-chloropyridin-2-yl)-N-(4,5-dihydro-1,3-thiazol-2-yl)pyrazole-3-carboxamide
  参考文献：
  名称：

  Synthesis, Insecticidal Activities, and SAR Studies of Novel Pyridylpyrazole Acid Derivatives Based on Amide Bridge Modification of Anthranilic Diamide Insecticides

  摘要：

  Anthranilic diamides are one of the most important classes of modern agricultural insecticides. To discover new structure-modified compounds with high activity, series of novel carbonyl thioureas, carbonyl ureas, oxadiazoles, carbonyl thiophosphorylureas, oxadiazole-containing amides, and thiazoline-containing amides were designed through the modification of the amide bridge based on the structure of chlorantraniliprole and were synthesized, and bioassays were carried out. The compounds were characterized and confirmed by melting point, IR, H-1 NMR, and elemental analyses or HRMS. Preliminary bioassays indicated that some compounds exhibited significant insecticidal activities against oriental armyworm, diamondback moth, beet armyworm, corn borer, and mosquito. Among them, trifluoroethoxyl-containing carbonyl thiourea 20a showed best larvicidal activity against oriental armyworm, with LC50 and LC95 values of 0.1812 and 0.7767 mg/L, respectively. Meanwhile, 20c and 20e showed 86 and 57% death rates against diamondback moth at 0.005 mg/L, and the LC50 values of the two compounds were 0.0017 and 0.0023 mg/L, respectively, which were lower than that of the control chlorantraniliprole. The relationship between structure and insecticidal activity was discussed, and the HF calculation results indicated that the carbonyl thiourea moiety plays an important role in the insecticidal activity. The present work demonstrated that the trifluoroethoxyl-containing carbonyl thioureas can be used as lead compounds for further development of novel insecticides.

  DOI：

  10.1021/jf4012467
• 作为产物：
  描述：

  4-氯-2-甲基苯基异硫氰酸酯 在 盐酸 作用下， 以 乙醚 、 水 为溶剂， 生成 2-硫杂氮醇胺,N-(4-氯-2-甲基苯基)-4,5-二氢-
  参考文献：
  名称：

  Synthesis, Insecticidal Activities, and SAR Studies of Novel Pyridylpyrazole Acid Derivatives Based on Amide Bridge Modification of Anthranilic Diamide Insecticides

  摘要：

  Anthranilic diamides are one of the most important classes of modern agricultural insecticides. To discover new structure-modified compounds with high activity, series of novel carbonyl thioureas, carbonyl ureas, oxadiazoles, carbonyl thiophosphorylureas, oxadiazole-containing amides, and thiazoline-containing amides were designed through the modification of the amide bridge based on the structure of chlorantraniliprole and were synthesized, and bioassays were carried out. The compounds were characterized and confirmed by melting point, IR, H-1 NMR, and elemental analyses or HRMS. Preliminary bioassays indicated that some compounds exhibited significant insecticidal activities against oriental armyworm, diamondback moth, beet armyworm, corn borer, and mosquito. Among them, trifluoroethoxyl-containing carbonyl thiourea 20a showed best larvicidal activity against oriental armyworm, with LC50 and LC95 values of 0.1812 and 0.7767 mg/L, respectively. Meanwhile, 20c and 20e showed 86 and 57% death rates against diamondback moth at 0.005 mg/L, and the LC50 values of the two compounds were 0.0017 and 0.0023 mg/L, respectively, which were lower than that of the control chlorantraniliprole. The relationship between structure and insecticidal activity was discussed, and the HF calculation results indicated that the carbonyl thiourea moiety plays an important role in the insecticidal activity. The present work demonstrated that the trifluoroethoxyl-containing carbonyl thioureas can be used as lead compounds for further development of novel insecticides.

  DOI：

  10.1021/jf4012467

文献信息

• 2-phenylimino-1,3-thiazolidin-3-organophosphorus compounds having
  申请人：Shionogi & Co., Ltd.

  公开号：US04720488A1

  公开（公告）日：1988-01-19

  A compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 each represent C.sub.1 -C.sub.5 alkoxy or C.sub.1 -C.sub.5 alkylthio, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 each represent hydrogen or C.sub.1 -C.sub.5 alkyl, R.sup.7, R.sup.8 and R.sup.9 each represent hydrogen, C.sub.1 -C.sub.5 alkyl or halogen, and X represents oxygen or sulfur. A process for preparing the compound (I) and a pesticidal composition containing the compound (I) are also provided.

  公式为：##STR1## 其中 R.sup.1 和 R.sup.2 分别代表 C.sub.1 -C.sub.5 烷氧基或 C.sub.1 -C.sub.5 烷硫基，R.sup.3、R.sup.4、R.sup.5 和 R.sup.6 分别代表氢或 C.sub.1 -C.sub.5 烷基，R.sup.7、R.sup.8 和 R.sup.9 分别代表氢、C.sub.1 -C.sub.5 烷基或卤素，X 代表氧或硫。还提供了制备化合物（I）的方法和含有化合物（I）的杀虫剂组合物。
• Organophosphorus compounds having pesticidal activity, their preparation and use
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0227363A1

  公开（公告）日：1987-07-01

  Compounds of the formula: wherein R¹ and R² each represent C₁-C₅ alkoxy or C₁-C₅ alkylthio, R³, R⁴, R⁵ and R⁶ each represent hydrogen or C₁-C₅ alkyl, R⁷, R⁸ and R⁹ each represent hydrogen, C₁-C₅ alkyl or halogen, and X represents oxygen or sulfur, are new and have pesticidal activity.

  式中 R¹ 和 R² 各自代表 C₁-C₅ 烷氧基或 C₁-C₅ 烷硫基，R³、R⁴、R⁵ 和 R⁶ 各自代表氢或 C₁-C₅ 烷基，R⁷、R⁸ 和 R⁹ 各自代表氢、C₁-C₅ 烷基或卤素，X 代表氧或硫的化合物是具有杀虫活性的新化合物。
• Hirashima, Akinori; Yoshii, Yutuka; Eto, Morifusa, Agricultural and Biological Chemistry, 1991, vol. 55, # 10, p. 2537 - 2546
  作者：Hirashima, Akinori、Yoshii, Yutuka、Eto, Morifusa

  DOI：——

  日期：——
• HAYASE, YOSHIO;ICHINARI, MITSUHIRO;KAMEI, KAZUO;TAGUCHI, JUNJI;OBA, KATSU+
  作者：HAYASE, YOSHIO、ICHINARI, MITSUHIRO、KAMEI, KAZUO、TAGUCHI, JUNJI、OBA, KATSU+

  DOI：——

  日期：——
• XAYASEH, JOSIO;ITINARI, MITSUXIRO;KAMEHI, KEHJO;TAGUTI, DZYUNDZI;OTA, KAT+
  作者：XAYASEH, JOSIO、ITINARI, MITSUXIRO、KAMEHI, KEHJO、TAGUTI, DZYUNDZI、OTA, KAT+

  DOI：——

  日期：——