Novel glycol benzyl ether herbicides: Herbicidal activity of 3,3a,5,9b-tetrahydro-2H-furo[3,2-c][2]benzopyran derivatives

• Kakimoto Takeshi

  Agrochemicals Group, Functional Chemicals Laboratory, R&D Center, Mitsui Chemicals, Inc.

• Koizumi Fumiaki

  Planning and Developing Group, Agrochemicals Division, Functional Chemicals and Engineered Materials Business Group, Mitsui Chemicals, Inc.

• Hirase Kangetsu

  Agrochemicals Group, Functional Chemicals Laboratory, R&D Center, Mitsui Chemicals, Inc.

• Arai Kiyoshi

  Agrochemicals Group, Functional Chemicals Laboratory, R&D Center, Mitsui Chemicals, Inc.

Bibliographic Information

Other Title

• 新規グリコールベンジルエーテル系除草剤 : 3,3a,5,9b-tetrahydro-2H-furo[3,2-c][2]benzopyran誘導体の除草活性

Abstract

The structure–activity relationship of novel glycol benzyl ether herbicides, 3,3a,5,9b-tetrahydro-2H-furo[3,2-c][2]benzopyrans (TFBs), was elucidated. Herbicidal activity against Echinochloa crus-galli and rice injury varied with substituents of the benzyloxy group at C-3. When substituents other than the benzyloxy group, such as the cyclohexylmethyloxy group or the benzoyloxy group, were introduced, the herbicidal activity of TFBs was reduced. Introduction of an (S)-methyl group at C-5 increased herbicidal activity but aggravated rice injury. When comparing the herbicidal activity of two stereoisomers, the 5-(S)-isomer showed stronger herbicidal activity than the 5-(R)-isomer. Even when the benzene ring of the fused ring system of TFB was replaced by thiophene or furan, high herbicidal activity was manifested. In particular, TFB partly replaced by thiophene showed the highest herbicidal activity among all compounds examined in this study, with slight injury to rice plants. The 2,6-dioxabicyclo[3,3,0]octane derivative, produced as a by-product, also showed high herbicidal activity.

Journal

• Journal of Pesticide Science

  Journal of Pesticide Science 31 (4), 380-389, 2006

  Pesticide Science Society of Japan

Keywords

• glycol benzyl ether herbicides
• 3,3a,5,9b-tetrahydro-2<i>H</i>-furo[3,2-<i>c</i>][2]benzopyrans
• <i>Echinochloa crus-galli</i>
• structure–activity relationship

Details

• CRID: 1390282680186792576
• NII Article ID: 110004850992
• NII Article ID: 130004445062
• NII Book ID: AA11818622
• DOI: 10.1584/jpestics.g06-03
• ISSN: 13490923
• ISSN: 03851559
• ISSN: 1348589X
• NDL BIB ID: 8582185
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I8582185
• Web Site: http://www.jstage.jst.go.jp/article/jpestics/31/4/31_4_380/_pdf
• Web Site: http://dl.ndl.go.jp/info:ndljp/pid/10877850
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • NDL-Digital
  • CiNii Articles
• Abstract License Flag: Disallowed