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The optical isomers, (R)‐1(α‐methylbenzyl)‐3‐p‐tolylurea ((R)‐MBU) and (S)‐1‐(α‐methylbenzyl)‐3‐p‐tolylurea ((S)MBU), which are analogues of daimuron [1‐(α,α‐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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The results presented here support the hypothesis that plants of the tribe Oryzeae respond enantioselectively and homogeneously to optically active 1-alpha-methylbenzyl-3-p-tolylurea (MBTU) in root growth inhibition, in contrast to Echinochloa species. The Oryzeae plants tested in this study belong to different genera (Oryza, Leersia, Chikusichloa and Zizania), to different species (O sativa, O glaberrima, O alta, O coarctata, O latifolia, O minuta, O rufipogon), to various ecospecies of Oryza (japonica, indica, japonica x indica, javanica) and to different levels of evolution [cultivated rice (O sativa and O glaberrima) and ancestral wild rice species]. In spite of their different phylogenic status and diverse sensitivity, the root growth of all members of the genus Oryza was inhibited more by R-MBTU than by S-MBTU. Zizania palustris, Z latifolia, Leersia oryzoides and Chikusichloa aquatica belonging to the tribe Oryzeae exhibited similar chiral recognition to the Oryza plants, suggesting that Oryzeae have a common chiral recognition mechanism in their response to optically active MBTUs. In contrast, Echinochloa plants (E crus-galli (L) Beauv var crus-galli and E colonum (L) Link), belonging into subfamily Panicoideae tribe Paniceae, responded in a different way, where their root growth was more sensitive to S-MBTU than to the antipodal R-MBTU. A reverse chiral response between the tribe Oryzeae and the genus Echinochloa was clearly indicated in this study. This diverse response may be relevant to Gramineae classification.

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