Herbicidal Activity and Molecular Similarity of 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-3-thiourea Derivatives

1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-3-thiourea 유도체의 제초활성과 분자 유사성

  • Soung, Min-Gyu (Division of Applied Biologies and Chemistry, College of Agriculture and Life Sciences, Chungnam National University) ;
  • Park, Kwan-Yong (Division of Applied Biologies and Chemistry, College of Agriculture and Life Sciences, Chungnam National University) ;
  • Song, Jong-Hwan (Korea Research Institute of Chemical Technology) ;
  • Sung, Nack-Do (Division of Applied Biologies and Chemistry, College of Agriculture and Life Sciences, Chungnam National University)
  • 성민규 (충남대학교 농업생명과학대학 응용생물화학부) ;
  • 박관용 (충남대학교 농업생명과학대학 응용생물화학부) ;
  • 송종환 (한국화학연구원 신약연구단) ;
  • 성낙도 (충남대학교 농업생명과학대학 응용생물화학부)
  • Published : 2008.09.30

Abstract

In the search for third generation herbicidal cyclic imide derivatives, the average values of herbicidal activity ($pI_{50}$) in vivo (pre-emergence) of 40 new peroxidizing herbicides, 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)thiourea derivatives (1-40) against rice plant (Orysa sativa) and barnyard grass (Echinochlor crus-galli) were studied. The molecular similarity between protoporphyrinogen IX (protogen) as the substrate of protox enzyme and Urea derivatives (1-40) was discussed quantitatively. The diallyl (20) and 3-nitro substituent (33) showed the selective herbicidal activity against barnyard grass. Allyl substituent (8) and their molecular similarity in dice (S=0.81) showed the highest levels of herbicidal activity ($pI_{50}$=4.71). Also, similarity indices (S) and superimposed volume (C) of protogen and aryl-substituents (21-40) showed good correlation.

제3세대 제초성 cyclic imide 유도체를 탐색하기 위하여 peroxidizing 제초제로써 40개의 1-(4-chloro-2-fluoro-5-pro-pargyloxypheny)-3-thiourea 유도체(1-40) 중, 3-R-치환체의 발아 전 벼(Oryza sativa)와 논피(Echinochlo crusglli)에 대한 평균 제초활성 값들을 제시하였다. 그리고 Urea 유도체(1-40)와 protox 효소의 기질분자인 protogen사이의 분자구조 유사성을 검토하였다. 논피에 대하여 선택성을 나타내는 화합물은 diallyl-치환체(20)와 3-nitro-치환체(33)이었으며 allyl-치환체(8)가 가장 큰 제초활성$(pI_{50}=4.71)$과 유사성 지수(S=0.81) 값을 나타내었다. 그리고 aryl-치환체(21-40)와 Protogen 사이의 중첩된 부피(C)와 S값 사이에 상관성이 좋았다.

Keywords

References

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