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Novel 3,3a,5,9b‐tetrahydro‐2 H ‐furo[3,2‐c][2] benzopyran derivatives: synthesis of chiral glycol benzyl ether herbicides
Author(s) -
Kakimoto Takeshi,
Koizumi Fumiaki,
Hirase Kangetsu,
Banba Shinichi,
Tanaka Eishi,
Arai Kiyoshi
Publication year - 2004
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.838
Subject(s) - intramolecular force , benzopyran , tricyclic , chemistry , ether , stereochemistry , echinochloa , ring (chemistry) , weed , organic chemistry , biology , botany
Novel tricyclic 3,3a,5,9b‐tetrahydro‐2 H ‐furo[3,2‐c][2]benzopyran (TFB) derivatives were synthesized, and their herbicidal activities were elucidated. They were synthesized from D ‐glucose as a natural chiral source. The formation of the TFB skeleton was achieved by a Friedel–Crafts type intramolecular cyclization of methyl 5‐deoxy‐2,3‐ O ‐dibenzyl‐5‐ C ‐methyl‐ D ‐xylofranosides. The intramolecular cyclization was dependent upon the electronic effects of the substituents at the C ‐2 benzyloxy group of methyl xylofranosides. Some TFBs exhibited a remarkable herbicidal activity to annual paddy weeds, such as Echinochloa sp, without injury to the rice. Copyright © 2004 Society of Chemical Industry