The Korean Journal of Pesticide Science (농약과학회지)

The Korean Society of Pesticide Science (한국농약과학회)
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Syntheses of Pyrrolo[2,1-b]thiazole Carboxanilides and Their Selective Antifungal Activities against Rice Blast and Wheat Leaf Rust

Pyrrolo[2,1-b]thiazole 카르복스아닐라이드 유도체의 합성 및 그들의 벼 도열병균과 밀 붉은녹병균에 대한 선택적인 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) ;
  • Yang, Bum-Seung (Organic Chemistry Lab, Korea Institute of Science and Technology) ;
  • Choe, Gyeong-Ja (Screening Division, Korea Research Institute of Chemical Technology) ;
  • Cho, Kwang-Yun (Screening Division, Korea Research Institute of Chemical Technology) ;
  • Lee, Seon-Woo (Screening Division, Korea Research Institute of Chemical Technology)
  • 한호규 (한국과학기술연구원, 생체과학연구부) ;
  • 남기달 (한국과학기술연구원, 생체과학연구부) ;
  • 양범승 (한국과학기술연구원, 생체과학연구부) ;
  • 최경자 (한국화학연구원 농약스크리닝팀) ;
  • 조광연 (한국화학연구원 농약스크리닝팀) ;
  • Published : 2005.06.30
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Abstract

For development of new agrochemical fungicide, syntheses of pyrrolo[2,1-b]thiazole carboxanilide derivatives 9 and antifungal screening against 6 kinds of plant pathogens were carried out. Functionalization of carboxylic acid on C-2 into carboxanilide in the pyrrolo[2,1-b]thiazole resulted in new 20 candidates, in which are ${\alpha},{\beta}$-unsaturated carboxanilide and methyl groups that are in cis relationship. Treatment of acetoxy-1,4-thiazin with magnesium in refluxing methanol gave pyrrolo[2,1-b]thiazole ethyl ester 4 in higher yield than that of the previous report. Hydrolysis of this compound afforded the corresponding acid 5, which reacted with aniline derivatives in the presence of coupling reagent, DIC to give pyrrolo[2,1-b]thiazole carboxanilides 9. As the result of in vivo antifungal assay of 9 against rice blast, rice sheath blight, cucumber gray mold, tomato late blight, wheat leaf rust, and barley powdery mildew, some compounds showed selectively antifungal activities against the rice blast and wheat leaf rust.

신농약 살균제 개발을 목적으로 pyrrolo[2,1-blthiazole carboxanilide 유도체 9를 합성하고 그들의 식물병원균 6종에 대한 항균력을 시험하였다. 한 분자 내에 피롤과 티아졸 moiety를 동시에 갖춘 이중헤테로고리 화합물인 pyrrolo[2,1-b]thiazole의 C-2 위치에 카르복스아닐라이드기를 도입하여 신규 후보화합물 20종을 합성하였다. 이 화합물은 ${\alpha}$,${\beta}$-불포화 카르복스아닐라이드기와 이것과 시스(cis)관계의 메틸기가 분자 내에 포함되어 있다. Acetoxy-1,4-thiazin 유도체 2를 메탄올 용액 중에서 마그네슘으로 처리하여 기존의 방법보다 더 높은 수율로 pyrrolo[2,1-b]thiazole 에틸에스테르 4를 얻었다. 이것을 가수분해한 다음 생성된 상응하는 카르복실산 5를 DIC 존재 하에서 아닐린 유도체와 반응시켜 pyrrolo[2,1-b]thiazole carboxanilide 유도체 9를 합성하였다. 화합물 9의 벼 도열병, 벼 잎집무늬마름병, 오이 잿빛곰팡이병, 토마토 역병, 밀 붉은녹병, 보리흰가루병 등에 대하여 (in vivo) 항균활성을 조사한 결과, 일부 화합물에서 벼 도열병(RCB, rice blast) 과 밀 붉은녹병(WLR, wheat leaf rust)에 대해서만 선택적 활성을 나타냈다.

Keywords

References

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