Synthesis and Herbicidal Activities of Tetrahydroindazole Derivatives Possessing Hydroxyalkyl Subgroup

하이드록시알킬 치환체를 갖는 테트라하이드로인다졸계 화합물의 합성과 제초활성 연구

  • Ko, Young-Kwan (Bio-organic Science Division, Korea Research Institute of Chemical Technology) ;
  • Chung, Kun-Hoe (Bio-organic Science Division, Korea Research Institute of Chemical Technology) ;
  • Ryu, Jae-Wook (Bio-organic Science Division, Korea Research Institute of Chemical Technology) ;
  • Woo, Jae-Chun (Bio-organic Science Division, Korea Research Institute of Chemical Technology) ;
  • Koo, Dong-Wan (Bio-organic Science Division, Korea Research Institute of Chemical Technology) ;
  • Choi, Jung-Sup (Bio-organic Science Division, Korea Research Institute of Chemical Technology) ;
  • Kim, Jun-Young (Bio-organic Science Division, Korea Research Institute of Chemical Technology) ;
  • Kim, Su-Ho (Bio-organic Science Division, Korea Research Institute of Chemical Technology) ;
  • Kim, Tae-Joon (Dongbu Hitec Agrolife Research Institute) ;
  • Choi, In-Young (Dongbu Hitec Agrolife Research Institute) ;
  • Seok, Mee-Young (Dongbu Hitec Agrolife Research Institute) ;
  • Choi, Jun-Hyuk (Dongbu Hitec Agrolife Research Institute) ;
  • Chung, Bong-Jin (Dongbu Hitec Agrolife Research Institute)
  • 고영관 (한국화학연구원 신약연구단) ;
  • 정근회 (한국화학연구원 신약연구단) ;
  • 류재욱 (한국화학연구원 신약연구단) ;
  • 우재춘 (한국화학연구원 신약연구단) ;
  • 구동완 (한국화학연구원 신약연구단) ;
  • 최정섭 (한국화학연구원 신약연구단) ;
  • 김준영 (한국화학연구원 신약연구단) ;
  • 김수호 (한국화학연구원 신약연구단) ;
  • 김태준 ((주)동부하이텍 농생명연구소) ;
  • 최인영 ((주)동부하이텍 농생명연구소) ;
  • 석미영 ((주)동부하이텍 농생명연구소) ;
  • 최준혁 ((주)동부하이텍 농생명연구소) ;
  • 정봉진 ((주)동부하이텍 농생명연구소)
  • Published : 2008.06.30

Abstract

As an ongoing research program for the development of environmental friendly new soil-surface treatment herbicide, several tetrahydroindazole derivatives 6a - 6h possessing hydroxyalkyl subgroup were synthesized and shown to have interesting herbicidal activities exhibiting sumptoms as protoporphyrinogen IX oxidase inhibitor under pre-emergence upland greenhouse screening. Among derivatives tested, compound 6f showed superior herbicidal activity against problem weeds.

References

  1. Boger, P., K. Wakanayashi and K. Hirai (Eds.) (2002) Herbicide classes in development: Mode of Action, Targets, Genetic Engineering, Chemistry, Springer, Berlin
  2. Hirai, K., A. Uchida and R. Ohno (2002) Major synthetic routes for modern herbicide classes and agrochemical characteristics, pp. 255-278, In Herbicide classes in development: Mode of Action, Targets, genetic Engineering, Chemistry (eds. Boger, P., K. Wakanayashi and K. Hirai), Springer, Berlin
  3. Matsumoto, H. (2002) Inhibition of protoporphyrinogen oxidase: a brief update, pp. 151-161, In Herbicide classes in development (ed. Boger, P. and K. Wakanayashi), Springer, Berlin
  4. Nishinomiya, E. N., I. T. Toyonaka, M. F. Takarazuka, R. Y. Kawanishi, H. M. Kakogawa (1989) 2-Substituted phenyl- 4,5,6,7-tetrahydro-2H-indazoles US patent 4,835,286
  5. 고영관, 정근회, 류재욱, 우재춘, 구동완, 김태준, 최정섭, 김대황, 정봉진, 김태준, 최인영, 석미영, 최준혁, 문기준 (2007) 테트라하이드로인다졸계 화합물 및 이를 포함하는 제초제. 대한민국 특허 출원 2007-0114770
  6. 류재욱, 정근회, 고영관, 우재춘, 구동완, 김태준, 최정섭, 박채현, 김대황 (2005) N-[4-cyano-2-fluoro-5-(substituted)phenyl]-3,4,5,6- tetrahydro phthalimide 유도체의 합성과 제초활성. 농약과학회지 9(1):108-111
  7. Hirai, K. (1999) Structural evolution and synthesis of diphenyl ethers, cyclic imides and related compounds. pp. 24-37, In peroxidizing herbicides (ed. Boger, P. and K. Wakanayashi), Springer, Berlin
  8. 고영관, 정근회, 류재욱, 우재춘, 구동완, 김태준, 최정섭, 김준영, 권오연, 정봉진, 김대황 (2006) 아미드 치환체를 갖는 히단토인계 화합물의 합성과 제초활성 연구. 농약과학회지 10(2):153-156
  9. 조광연 (1998) 신농약 효능검사 및 기반기술연구, p. 901, 과학기술부 선도기술개발 사업 2단계 최종보고서