title: Novel 3,3a,5,9b-tetrahydro-2H-furo[3,2-c][2] benzopyran derivatives: synthesis of chiral glycol benzyl ether herbicides.
abstract: Novel tricyclic 3,3a,5,9b-tetrahydro-2H-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.
authors.affiliation: Agrochemicals Group, Functional Chemicals Laboratory, R&D Centre, Mitsui Chemicals, Inc, 1144 Togo, Mobara, Chiba 297-0017, Japan. takeshi.kakimoto@mitsui-chem.co.jp
authors.forename: Takeshi
authors.initials: T
authors.lastname: Kakimoto
authors.forename: Fumiaki
authors.initials: F
authors.lastname: Koizumi
authors.forename: Kangetsu
authors.initials: K
authors.lastname: Hirase
authors.forename: Shinichi
authors.initials: S
authors.lastname: Banba
authors.forename: Eishi
authors.initials: E
authors.lastname: Tanaka
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Arai
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis* / Q000633:toxicity; D001593:Benzyl Compounds / Q000138:chemical synthesis / Q000633:toxicity; D031747:Echinochloa / Q000187:drug effects*; D006018:Glycols / Q000138:chemical synthesis / Q000633:toxicity; D006540:Herbicides / Q000138:chemical synthesis* / Q000633:toxicity; D015394:Molecular Structure
chemical_list: D001578:Benzopyrans; D001593:Benzyl Compounds; D006018:Glycols; D006540:Herbicides