Novel 3,3a,5,9b-tetrahydro-2H-furo[3,2-c][2] benzopyran derivatives: synthesis of chiral glycol benzyl ether herbicides.
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.
Kakimoto
Takeshi
T
Agrochemicals Group, Functional Chemicals Laboratory, R&D Centre, Mitsui Chemicals, Inc, 1144 Togo, Mobara, Chiba 297-0017, Japan. takeshi.kakimoto@mitsui-chem.co.jp
Koizumi
Fumiaki
F
Hirase
Kangetsu
K
Banba
Shinichi
S
Tanaka
Eishi
E
Arai
Kiyoshi
K
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
D001578:Benzopyrans; D001593:Benzyl Compounds; D006018:Glycols; D006540:Herbicides