Mechanism of Safening Action of Dymuron and Its Two Monomethyl Analogues against Bensulfuron-methyl Injury to Rice (Oryza sativa)

Omokawa, Hiroyoshi; Wu, Jun; Hatzios, Kriton K.

doi:10.1006/pest.1996.0035

Cited by 31 publications

(23 citation statements)

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“…Deng and Hatzios (2003) reported that M1, M2, and M4 appeared to be the major metabolites, without detecting any M3, 24 h after treatment. However, M3 was reported to be one of the major metabolites 3 d after treatment (Omokawa et al, 1996). Although we observed a significant increase in CYP81A6 expression in leaves 88 h post-treatment in the present study (Fig.…”

Section: Discussioncontrasting

confidence: 51%

Expression of cytochrome P450 CYP81A6 in rice: tissue specificity, protein subcellular localization, and response to herbicide application

Edwards

Wang

et al. 2015

J. Zhejiang Univ. Sci. B

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Abstract:The cytochrome P450 gene CYP81A6 confers tolerance to bentazon and metsulfuron-methyl, two selective herbicides widely used for weed control in rice and wheat fields. Knockout mutants of CYP81A6 are highly susceptible to both herbicides. The present study aimed to characterize the CYP81A6 expression in rice. Quantitative real-time polymerase chain reaction (PCR) analyses demonstrated that foliar treatment of bentazon (500 mg/L) greatly induced expression of CYP81A6 in both wild-type (Jiazhe B) and its knockout mutant (Jiazhe mB): a 10-fold increase at 9 h before returning to basal levels at 24 h in Jiazhe B, while in the mutant the expression level rose to >20-fold at 12 h and maintained at such high level up to 24 h post exposure. In contrast, metsulfuron-methyl (500 mg/L) treatment did not affect the expression of CYP81A6 in Jiazhe B within 80 h; thereafter the expression peaked at 120 h and returned gradually to basal levels by Day 6. We suggest that a metabolite of metsulfuron-methyl, 1H-2,3-benzothiazin-4-(3H)-one-2,2-dioxide, is likely to be responsible for inducing CYP81A6 expression, rather than the metsulfuronmethyl itself. Use of a promoter-GUS reporter construct (CYP81A6Pro::GUS) demonstrated that CYP81A6 was constitutively expressed throughout the plant, with the highest expression in the upper surfaces of leaves. Subcellular localization studies in rice protoplasts showed that CYP81A6 was localized in the endoplasmic reticulum. These observations advance our understanding of CYP81A6 expression in rice, particularly its response to the two herbicides.

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Section: Discussioncontrasting

confidence: 51%

Expression of cytochrome P450 CYP81A6 in rice: tissue specificity, protein subcellular localization, and response to herbicide application

Edwards

Wang

et al. 2015

J. Zhejiang Univ. Sci. B

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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%

“…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: 99%

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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“…In particular, the carbamothioate herbicides, such as dimepiperate, and the urea herbicides, such as dymron, were shown to have some ability to protect rice against stunting injury caused by sulfonylurea herbicides 11. 14–17 The enhancement of sulfonylurea herbicide metabolism, including O ‐demethylation, in the presence of safeners has been demonstrated in vivo 11. 13, 14 However, no evidence was found regarding the formation of the O ‐desmethyl metabolite of PSE in vitro , and there is limited information about cytochrome P‐450‐dependent enzymes related to safening effects against sulfonylurea herbicide injury.…”

Section: Introductionmentioning

confidence: 99%

Involvement of cytochrome P‐450 enzyme activity in the selectivity and safening action of pyrazosulfuron‐ethyl

Yun¹,

Shim

Usui

2001

Pest Management Science

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To investigate the selectivity and safening action of the sulfonylurea herbicide pyrazosulfuron-ethyl (PSE), pyrazosulfuron-ethyl O-demethylase (PSEOD) activity involving oxidative metabolism by cytochrome P-450 was studied in rice (Oryza sativa L cv Nipponbare) and Cyperus serotinus Rottb. Cytochrome P-450-dependent activity was demonstrated by the use of the inducers 1,8-naphthalic anhydride and ethanol, the herbicides PSE, bensulfuron-methyl, dimepiperate and dymron, or the inhibitor piperonyl butoxide (PBO). Growth inhibition in C serotinus seedlings was more severe than that in rice seedlings. O-Dealkylation activities of PSE were induced differently in rice and in C serotinus, with distinctly higher activity in rice seedlings. The induced PSEOD activities were slightly inhibited by PBO in rice seedlings, whereas they were strongly inhibited in C serotinus seedlings. Dimepiperate and dymron were effective safeners of rice against PSE treatment. Treatments with herbicide alone resulted in less induction of PSEOD activity compared with combined treatments of the herbicide and safener. PSEOD activity in rice seedlings induced with herbicide alone was strongly inhibited by PBO, whereas it was weakly inhibited in rice seedlings induced with combinations of PSE and two safeners. These results suggest that O-demethylation by cytochrome P-450 enzymes may be involved in the metabolism of PSE and may contribute to its selectivity and safening action. Furthermore, these results suggest the existence of a multiple form of cytochrome P-450 in plants.

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Mechanism of Safening Action of Dymuron and Its Two Monomethyl Analogues against Bensulfuron-methyl Injury to Rice (Oryza sativa)

Cited by 31 publications

References 0 publications

Expression of cytochrome P450 CYP81A6 in rice: tissue specificity, protein subcellular localization, and response to herbicide application

Expression of cytochrome P450 CYP81A6 in rice: tissue specificity, protein subcellular localization, and response to herbicide application

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

Involvement of cytochrome P‐450 enzyme activity in the selectivity and safening action of pyrazosulfuron‐ethyl

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Mechanism of Safening Action of Dymuron and Its Two Monomethyl Analogues against Bensulfuron-methyl Injury to Rice (Oryza sativa)

Cited by 31 publications

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Expression of cytochrome P450 CYP81A6 in rice: tissue specificity, protein subcellular localization, and response to herbicide application

Expression of cytochrome P450 CYP81A6 in rice: tissue specificity, protein subcellular localization, and response to herbicide application

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

Involvement of cytochrome P‐450 enzyme activity in the selectivity and safening action of pyrazosulfuron‐ethyl

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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