Interaction between optical isomerism and plant pharmacological action, change of modes of action and chirality of 1-(alpha-methylbenzyl)-3-p-tolylutea
1993
Omokawa, H. | Kawata, Y. | Konnai, M.
The optical isomers, (R)-1-(alpha-methylbenzyl)-3-p-tolylurea ((R)-MBU) and (S)-1-(alpha-methylbenzyl)-3-p-tolylurea ((S)-MBU), which are analogues of daimuron [1-(alpha,alpha-dimethylbenzyl)-3-p-tolylurea], a herbicide for Cyperaceae weeds and a safener for paddy rice, exhibited different biological responses. These two physiological properties of daimuron were observed separately in (R)-MBU and (S)-MBU. Only (R)-MBU had herbicidal activity against Cyperaceae weeds, while the (S)-isomer was a more effective safener against bensulfuron-methyl (BSM) injury of rice seedlings than was (R)-MBU, (S)-MBU promoted root growth of rice seedlings, but the (R)-enantiomer inhibited root growth. (S)-MBU was a more potent inhibitor than (R)-MBU on PS II reaction of spinach broken chloroplasts. Furthermore, (S)-MBU and (R)-MBU showed cross intergenus selective phytotoxicity among the Gramineae plants, Oryza sativa L. (rice, cv. Tsukinohikari, japonica), Triticum aestivum L. (wheat, cv. Norin No. 61) and Echinochloa crusgalli var. frumentacea Wight, on root growth inhibition in the dark.
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