Design of new 1,3-thiazoline derivatives by isosterism and antifungal activity of new 2,4-diimino-1,3-thiazolidines

Isosterism을 이용한 새로운 1,3-thiazoline 유도체의 디자인 및 신규 2,4-diimino-1,3-thiazolidine 유도체의 살균 활성

  • Hahn, Hoh-Gyu (Organic Chemistry Lab, Korea Institute of Science and Technology) ;
  • Nam, Kee-Dal (Organic Chemistry Lab, Korea Institute of Science and Technology) ;
  • Lim, Chul-Soo (Organic Chemistry Lab, Korea Institute of Science and Technology) ;
  • Mah, He-Duck (Department of Chemisty, Kyonggi University) ;
  • Kim, Jin-Cheol (Screening Division, Korea Research Institute of Chemical Technology) ;
  • Cho, Kwang-Yun (Screening Division, Korea Research Institute of Chemical Technology)
  • 한호규 (한국과학기술연구원 생체과학연구부) ;
  • 남기달 (한국과학기술연구원 생체과학연구부) ;
  • 임철수 (한국과학기술연구원 생체과학연구부) ;
  • 마혜덕 (경기대학교 화학과) ;
  • 김진철 (한국화학연구원 농약활성연구실) ;
  • 조광연 (한국화학연구원 농약활성연구실)
  • Published : 2003.03.27

Abstract

For the purpose of a development of new agrochemical fungicides, new compound 4 in which 1,3-thiazoline scaffold as well as urea moiety in the structure was designed through molecular modification of lead compound, 2-imino-1,3-thiazone based on isosterism. The reaction of N-alkylthiourea 5 and bromoacetonitrile in ethanol gave 2,4-diimino-1,3-thiazolidine hydrobromide 6 regioselectively, which was treated with isocyanates gave the corresponding 8 which is tautomer of 4. Antifungal screening (in vivo) of the synthesized compound 8 against typical plant diseases, which include rice blast, rice sheath blight, cucumber gray mold, tomato late blight, wheat leaf rust, and barley powdery mildew, was carried out. Antifungal activities against rice blast of the compound 8 were weaker than those of 2-phenylimino-1,3-thiazoline 1. Some compounds showed weak antifungal activities against wheat leaf rust.

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