Enantioselective Relieving Activity of α-Methylbenzylphenylureas toward Bensulfuron-methyl Injury to Rice (<i>Oryza sativa</i>)

Omokawa, Hiroyoshi; Ryoo, Jae Hwan; Kashiwabara, Sanae

doi:10.1271/bbb.63.349

Cited by 10 publications

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“…They also show stress‐relieving activity towards herbicide and sodium chloride influence (by the ( S )‐enantiomers) 21, 23–25. Two chiral pairs (( R )‐/( S )‐1‐α‐methylbenzyl‐3‐ p ‐tolylureas ( R ‐MBTU and S ‐MBTU) and ( R )‐/( S )‐1‐α‐methylbenzyl‐3‐ m ‐tolylureas) exhibited a cross intergenus selective phytotoxicity 21, 24, 26. The root growth of Oryza sativa L (cvs Tsukinohikari, Japonica, and Lemont, Japonica × Indica) is more inhibited by the ( R )‐enantiomer and that of Triticum aestivum L, Zea mays L and Echinochloa crus‐galli (L) Beauv var frumentacea Wight (barnyard millet) by the ( S )‐antipode 21.…”

Section: Introductionmentioning

confidence: 99%

Chiral response of Oryzeae and Paniceae plants in α‐methylbenzyl‐3‐p‐tolyl urea agar medium

Omokawa

Murata

Kobayashi

2003

Pest Management Science

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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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Section: Introductionmentioning

confidence: 99%

Chiral response of Oryzeae and Paniceae plants in α‐methylbenzyl‐3‐p‐tolyl urea agar medium

Omokawa

Murata

Kobayashi

2003

Pest Management Science

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“…Optically active urea compounds (2-7) and daimuron have been found eŠective stress relievers of rice injured with the bensulfuron-methyl herbicide. 22,23,26) The data in Table 1 show the root-growth response of the just-germinated rice seedlings after treatment with 60 mM NaCl or with a stress reliever and with their combination in the agar culture medium. At this concentration of NaCl, the root growth rate was only 46.5z of the control value.…”

Section: Resultsmentioning

confidence: 99%

“…An analytical approach by the safener index (SI) is useful for comparing the potency of stress relievers as described in a previous paper. 23) The average safener index (SI(AV)) is also shown in Table 1. Both the optically active urea stress relievers, 3 and 7, exhibited high SI(AV) values, but the value for daimuron was 22.2.…”

Section: Resultsmentioning

confidence: 99%

“…frumentacea Wight in the dark, and stress relieving activity against herbicide stress in rice. 22,23,26) Concomitant treatment with S-MBPUs (2-7) eŠectively ameliorated the growth inhibition of roots of NaCltreated rice plants. Salt-stressed rice plants decrease their dry weight, protein content, water content and chlorophyll content.…”

Section: Discussionmentioning

confidence: 98%

“…22) The test compounds in this study (3)(4)(5)(6)(7) were developed as potent stress reliever for rice injured with the herbicide, bensulfuron-methyl (Londax), after the modiˆcation of 2. 23) We conducted this study to assess the amelioration potency of optically active MBPUs to the saltstressed growth of just-germinated rice seedlings, and discuss the relationship between the growth inhibition, Na + and protein contents, and dry weight. Our results indicate that S-MBPUs alleviated salt-stressed growth reduction and controlled the S W R(Na+) ratio approaching the non-stressed growth condition (NaCl at 3 mM).…”

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Amelioration of the Salt-stressed Root Growth of Rice and Normalization of the Na⁺Distribution between the Shoot and Root by (S)-α-Methylbenzyl-2-fluoro-4-methylphenylurea

Omokawa

Aonuma

2002

Bioscience, Biotechnology, and Biochemistry

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Optically active alpha-methylbenzyl phenyl ureas (MBPUs) show diverse plant physiological properties. Experiments were conducted to evaluate the salt-stress response of just-germinated rice seedlings supplemented with the S-enantiomer of MBPUs by assessing the growth and Na+ content. This study indicates that S-MBPUs served as a unique stress reliever for just-germinated young seedlings of rice injured by salinity. NaCl severely affected the root growth of rice seedlings. Concomitant treatment with S-MBPUs effectively ameliorated the growth inhibition of rice by NaCl. Glycine betaine (GB) did not act as a reliever of the NaCl stress. The addition of S-alpha-methylbenzyl 2-fluoro-4-methylphenyl urea (7, denoted as S-FM) to the saline medium ameliorated not only the root growth but also the protein content and dry weight of roots depending upon its concentration. The protein content, Na+ content and growth rate were correlated to each other with a positive relationship. The Na+ distribution ratio (S/R(Na+)) between the shoot and root increased with increasing concentration of NaCl when added alone, viz. with increasing growth reduction. A concomitant treatment with S-FM (7), however, resulted in the S/R(Na+) value becoming smaller with growth amelioration. This indicates that S-FM (7) controlled the translation of Na+ from the roots to shoots. S-FM (7) would have influenced some inherent functions connected with the Na+ behavior in the rice plant, although details of the mechanism for normalization of the S/R(Na+) ratio are still not clear.

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Enantioselective Response of Rice and Barnyard Millet on Root Growth Inhibition by Optically Active α-Methylbenzyl Phenylureas

Omokawa

Ryoo

2001

Pesticide Biochemistry and Physiology

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Enantioselective Relieving Activity of α-Methylbenzylphenylureas toward Bensulfuron-methyl Injury to Rice (Oryza sativa)

Cited by 10 publications

References 11 publications

Chiral response of Oryzeae and Paniceae plants in α‐methylbenzyl‐3‐p‐tolyl urea agar medium

Chiral response of Oryzeae and Paniceae plants in α‐methylbenzyl‐3‐p‐tolyl urea agar medium

Amelioration of the Salt-stressed Root Growth of Rice and Normalization of the Na⁺Distribution between the Shoot and Root by (S)-α-Methylbenzyl-2-fluoro-4-methylphenylurea

Enantioselective Response of Rice and Barnyard Millet on Root Growth Inhibition by Optically Active α-Methylbenzyl Phenylureas

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Enantioselective Relieving Activity of α-Methylbenzylphenylureas toward Bensulfuron-methyl Injury to Rice (Oryza sativa)

Cited by 10 publications

References 11 publications

Chiral response of Oryzeae and Paniceae plants in α‐methylbenzyl‐3‐p‐tolyl urea agar medium

Chiral response of Oryzeae and Paniceae plants in α‐methylbenzyl‐3‐p‐tolyl urea agar medium

Amelioration of the Salt-stressed Root Growth of Rice and Normalization of the Na+Distribution between the Shoot and Root by (S)-α-Methylbenzyl-2-fluoro-4-methylphenylurea

Enantioselective Response of Rice and Barnyard Millet on Root Growth Inhibition by Optically Active α-Methylbenzyl Phenylureas

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Amelioration of the Salt-stressed Root Growth of Rice and Normalization of the Na⁺Distribution between the Shoot and Root by (S)-α-Methylbenzyl-2-fluoro-4-methylphenylurea