Influence of 3-(N-methyl-N-X(sub.)phenylaminooxoacetyl) group on the herbicidal activity of Imazethapyr derivatives

Imazethapyr 유도체의 제초활성에 미치는 3-(N-methyl-N-(X)-치환-phenylaminooxoacetyl) group의 영향

  • Sung, N.D. (Department of Agricultural Chemistry, Chungnam National University) ;
  • Kim, H.J. (Kyung-Buk Agrochemical Co Ltd.) ;
  • Chang, H.S. (Korea Research Institute of Chemical Technology) ;
  • Kim, D.W. (Korea Research Institute of Chemical Technology)
  • Published : 1993.10.31

Abstract

New twenty five Imazethapyr derivatives, [2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin -2-yl)-3-(N-methyl-N-X(sub.)-phenylaminooxoacetyl)-5-methylpyridine] were synthesized. and The quantitative structure activity relationships (QSARs) between their post-emergence herbicidal activity$(pI_{50})$ values in vivo against Barnyard grass (Echinochloa crus-galli) and physicochemical parameters of substituents(X) of 3-(N-methyl-N-X(sub.)-phenylaminooxoacetyl) group have been studied. From the basis on the findings, in case of post-emergence, the activities were dependent on the steric constant$(E_s<0)$ and electron donating $(\sigma<0)$ effect by subsitituents(X) of 3-(N-methyl-N-X(sub.)phenylaminooxoacetyl) group. Therefore, The most effective compound,15 (4-t-butyl group) and 20 (3,5-dimethyl group) were examined in this study. And the conditions on the compounds predicted to show higher herbicidal activity were also discussed.

새로운 25종의 Imazethapyr 유도체, (2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-(N-methyl-N-(X)치환-phenylaminooxoacetyl)-5-methylpyridine)들을 합성하여 치환기(X) 변화에 따른 발아 전 후, 피(Echinochla crus-galli.)의 제초활성에 미치는 3-(N-mothy-N-(X)치환-phenylaminoozoacetyl) group의 영향을 검토한 바, 발아 전보다 발아 후의 제초활성에 더 큰 영향을 미침을 알 수 있었다. 발아 후의 제초활성은 X-치환기의 전자밀게 효과와 입체상수 $(E_s)$에 의존적이었으며 가장 큰 제초활성을 나타내는 화합물로는 $bulky(E_s<0)$하고 전자밀게$(\sigma<0)$가 치환된 화합물, 15(4-t-butyl group)와 20(3,5-dimethyl group)이었다. 그리고 높은 제초활성을 나타낼 것으로 예상되는 화합물의 조건들이 검토되었다.

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