Synthesis of combinatorial library of $\beta$-ketoacetoanilide chlorides and their antifungal activity against main plant pathogens

$\beta$-Ketoacetoanilide 염화물의 조합 라이브러리 합성 및 주요 식물병원균에 대한 항균활성

  • Hahn, Hoh-Gyu (Organic Chemistry, Lab, Korea Institute of Science and Technology) ;
  • Nam, Kee-Dal (Organic Chemistry, Lab, Korea Institute of Science and Technology) ;
  • Bae, Su-Yeal (Organic Chemistry, Lab, Korea Institute of Science and Technology) ;
  • Yang, Bum-Seung (Department of Chemistry, Kyonggi University) ;
  • Lee, Seon-Woo (Screening Division, Korea and Research Institute of Chemical Technology) ;
  • Cho, Kwang-Yun (Screening Division, Korea and Research Institute of Chemical Technology)
  • 한호규 (한국과학기술연구원 생체과학연구부) ;
  • 남기달 (한국과학기술연구원 생체과학연구부) ;
  • 배수열 (한국과학기술연구원 생체과학연구부) ;
  • 양범승 (경기대학교 화학과) ;
  • 이선우 (한국화학연구원 생물기능연구팀) ;
  • 조광연 (한국화학연구원 생물기능연구팀)
  • Published : 2004.03.30

Abstract

A synthesis of new $\beta$-ketoacetoanilide chloride derivatives and anti fungal activity of these compounds library against 6 typical plant pathogens were described. Reaction of ketene dimer with chlorine followed by treatment of aniline derivatives gave 89 kinds of the corresponding $\beta$-ketoacetoanilide chlorides through combinatorial synthetic technology using Carousel Reaction Stations. Evaluation of antifungal activity (in vivo) of this chemical library against rice blast, rice sheath blight, tomato aray mold, tomato late blight, wheat leaf rust and barley powdery mildew was carried out. In general, $\beta$-ketoacetoanilide chlorides which present a substituent at 4 in phenyl group(para) of the compounds showed selective control activity against tomato late blight caused by Phytophthora infestans.

베타-케토아세트아닐라이드 염화물 유도체의 합성 및 이들 화합물의 대표적인 6종의 식물병원균에 대한 항균력을 조사하였다. Carousel Reaction Stations 장치를 이용하여 조합 합성 기법을 통하여 키틴 이합 체를 염소와 아닐린 유도체와 차례로 반응시켜 89종의 베타-케토아세트아닐라이드 클로라이드 유도체를 얻었다. 합성된 화합물 라이브러리의 항균력(in vivo)을 벼 도열병, 벼 잎집무늬마름병, 토마토 잿빛곰팡이병, 토마토 잎마름역병, 밀 붉은녹병, 보리 흰가루병 등의 주요 식물병에 대한 항균력 시험을 수행하였다. 일반적으로 페닐기의 4위치 (para) 치환체가 존재하는 화합물의 경우에 선택적으로 토마토 잎마름역병을 방제하였다.

Keywords

References

  1. Adel, N., A. M. Richard and A. H. Richard (2002) Parallel Solid-Phase Synthesis of Disubstituted 1,6-Piperazine-2-ones. J. Combi. Chem. 4:542-545
  2. Alber, G., J. Curtze, and S. A. Drandarevski (1988) Dimethomoph (CME151), a novel curative fungicide. Proc. Br. Crop Prot. Conf. Pests Dis:17
  3. Clemens, R. J. (1986) Diketene. Chem. Rev. 86:241
  4. Davidse, L. C. and M. A. de Waard(1984) Systemic fungicides. Adv. Plant Pathol. 2:191-257
  5. Davidse, L. C. (1987) Biochemical aspects of phenylamide fungicides - action and resistance. p. 275, In Modem Selective Fungicides(ed. Lyr, H.), Longman Scientific, Essex, UK
  6. Egan, A. R., E. L. Michelotti, D. H. Young, W. J. Wilson and H. Mattioda (1998) RH-7281: A novel fungicide for control of downy mildew and late blight. Proc. Br. Crop Prot. Conf. Pests Dis.335-340
  7. Hawksworth, D. L., Kirk, P. M., Sutton, B. C. and Pegler, D. N. (1995) Anisworth & Bisby’s Dictionary of the Fungi. 8th ed. IMI. CAB International
  8. Joshi, M. M. and J. A. Sternberg (1996) DPX-JE874: a broad-spectrum fungicide with a new mode of action, in Proc. Brighton Crop Prot Conf.-Pests and Diseases, British Crop Protection Council, Farnham, UK, pp 21-26
  9. Kendall, S. J. and D. W. Hollomon (1998) Fungicide resistance. pp.87-108 In Fungicidal Activity(ed. Hutson, D. and J. Miyamoto), John Wiley & Sons, Chichester, UK
  10. Milani, S., S. Araki, N. Matsuo and P. Camblin (1998) IKF-916-a novel systemic fungicide for the control of oomycete plant diseases, in Proc. Brighton Crop Protect Conf.-Pests Dis., BCPC, Farnham, Surrey, UK, pp.351-358
  11. 한호규, 남기달, 신선호, 마혜덕 (2001) 2-Phenylimino-1,3-thiazoline 염산염 유도체의 합성. 한국농약과학회지 5(1):13-17
  12. 한호규, 남기달, 임철수, 마혜덕, 김진철, 조광연 (2003) Isosterism을 이용한 새로운 1,3-thiazoline 유도체의 디자인 및 신규 2,4-dimino-1,3-thiazolidine 유도체의 살균활성. 한국농약과학회지 7(2):51-57