Synthesis of New 2,4-Diimino-1,3-thiazoles and the Structure Determination

새로운 2,4-Diimino-1,3-thiazoles 유도체의 합성과 구조 결정

  • Published : 2003.02.20


For the purpose of developing new agrochemical fungicides, compound 2 possessing 1,3-thiazole scaffold as well as urea moiety in the structure was designed through molecular modification of lead compound, 2-imino-1,3-thiazoline based on isosterism. The reaction of N-methylthiouea 5 and bromoacetonitrile in ethanol gave 2,4-diimino-1,3-thiazole 4 regioselectively, which was treated with phenyl isocyanates to give the corresponding 7 which is tautomer of 2. The structural assignment of 7 was confirmed by various spectra($^1H$ NMR, $^{13}C$ NMR, FT-IR, HRMS), and X-ray crystallographic data. Compound 8 which is a structural isomer of 7 was formed through thermodynamically unstable intermediate 2,4-diimino-1,3-thiazole 6.


Isosterism;Agrochemical Fungicide


  1. Hahn, H.-G.; Nam, K. D.; Kim, B. S.; Cho, K. Y. Agri. Chem. and Biotechnol. 1997, 40, 139.
  2. Patani, G. A.; Lavoie, E. J. Chem. Rev. 1996, 96, 3147.
  3. Kavalek, J.; Jirman, J.; Sterba, V. Collect. Czech. Chem. Commun. 1985, 50, 766.
  4. Hahn, H.-G.; Shin, S.-H.; Mah, H. J. Korean Chem. Soc. 2001, 45, 612.

Cited by

  1. Substituent effects of thiazoline derivatives for fungicidal activities against Magnaporthe grisea vol.99, pp.2, 2011,