ジノテフラン誘導体の合成と構造活性相関 : ニトログアニジン部の修飾 Synthesis and Structure-Activity Relationships of Dinotefuran Derivatives : Modification in the Nitroguanidine Part

Abstract

ジノテフランは,ピリジン様骨格の換わりに特徴的なテトラヒドロ-3-フリルメチル基を有する新規ネオニコチノイド系殺虫剤である.ジノテフラン類縁体を合成し,半翅目に対する殺虫活性を調べた.ジノテフランのニトログアニジン部位の構造活性相関を要約すると以下の通りである.1)ニトロイミノ体およびニトロメチレン体の開環タイプは,N-モノメチル基が最も高い活性を示し.2)閉環タイプは開環タイプに比べ,ツマグロヨコバイで同等の活性を示したが,ヒメトビウンカでは10分の1に活性が低下した.3)開環,閉環タイプ共に,アシル基の導入により活性は殆ど変化しなかった.以上の結果を基に,ジノテフランが開発化合物に選ばれた.

Dinotefuran ((RS) -1-methyl-2-nitro-3- (tetrahydro-3-furylmethyl) guanidine) is a new neonicotinoid which has a characteristic (±) -tetrahydro-3-furylmethyl moiety instead of the pyridine-like moiety of other neonicotinoids. A series of dinotefuran derivatives were synthesized and tested against hemiptera. SAR (structure-activity relationships) of the nitroguanidine part of dinotefuran are summarized as follows : (1) the mono-methyl group as a N-substituent gave the best activity for the acyclic nitroimino and nitromethylene compounds, (2) the acyclic compounds showed the same activity as the cyclic compounds against Nephotettix cincticeps and were superior to them against Laodelphax striatellus, (3) N-acylation of this series scarcely changed the level of activity. On the basis of these results, we selected dinotefuran for development.

Journal

Journal of pesticide science   [List of Volumes]

Journal of pesticide science 29(4), 348-355, 2004-11-20  [Table of Contents]

Pesticide Science Society of Japan

Cited by:  1

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Codes

  • NII Article ID (NAID) :
    110001711179
  • NII NACSIS-CAT ID (NCID) :
    AA11818622
  • Text Lang :
    ENG
  • Article Type :
    Journal Article
  • ISSN :
    1348589X
  • NDL Article ID :
    7157252
  • NDL Source Classification :
    ZR7(科学技術--農林水産--農産)
  • NDL Call No. :
    Z18-1132
  • Databases :
    CJPref  NDL  NII-ELS 

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