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

• Published in: Pest management science 2004-05, Vol.60 (5), p.493-500
• Main Authors: Kakimoto, T, Koizumi, F, Hirase, K, Banba, S, Tanaka, E, Arai, K
• Format: Article
• Language: English
• Subjects: 2-c]benzopyran; 3,3a,5,9b‐tetrahydro‐2H‐furo[3,2‐c]benzopyran; 9b-tetrahydro-2H-furo; Benzopyrans - chemical synthesis; Benzopyrans - toxicity; Benzyl Compounds - chemical synthesis; Benzyl Compounds - toxicity; biochemical pathways; Biological and medical sciences; chemical reactions; Echinochloa; Echinochloa - drug effects; Echinochloa sp; Fundamental and applied biological sciences. Psychology; glycol benzyl ether herbicides; Glycols - chemical synthesis; Glycols - toxicity; herbicidal properties; Herbicides; Herbicides - chemical synthesis; Herbicides - toxicity; Hydrocarbons; intramolecular cyclization; Molecular Structure; natural chiral source; new products; Oryza sativa; Parasitic plants. Weeds; Phytopathology. Animal pests. Plant and forest protection; rice; synthesis; weed control; Weeds
• ISSN: 1526-498X; 1526-4998
• DOI: 10.1002/ps.838

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.