• Korean Journal of Weed Science
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• v.18 no.1
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• pp.28-35
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• 1998

Cyhalofop/bentazon ME and pyribenzoxim EC herbicides were originally developed as foliarapplied herbicides to control weeds at 4-5 leaf stages of barnyard grass 20-25 days after seeding (DAS) in direct-seeding culture but further possible utilization of these two herbicides earlier than 3-4 leaf stages of rice were evaluated for a field where early weed infestations might be severe. The application of cyhalofop/bentazon ME and pyribenzoxim EC at right after rice emergence and the 2-3 leaf stages of rice had an excellent weed control efficacy with above 90% up to 30 DAS without a phytotoxicity of rice plant and the control efficacy of over 80% was maintained until 60 DAS. However, these two herbicides controlled Echinochloa crus-galli very effectively above 97% but Aneilema keisak and Aeschynomene indica were not controlled by cyhalofop/bentazon ME and Cyperus serotinus by pyribenzoxim EC. Therefore, to control those problem weeds, second systematic application of pyribenzoxim EC and pyrazosulfuron/mefenacet G for A. keisak and A. indica, and pyrazosulfuron/molinate G, cyhalofap/ azimsulfuron/molinate G, pyrazosulfuron/mefenacet G and bentazon SL for C. serotinus at 30 DAS was found to be very efficient herbicide systems.

• The Korean Journal of Pesticide Science
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• v.3 no.2
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• pp.19-28
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• 1999

To investigate the physiological and biochemical differences between susceptible and tolerant species of Echinochloa species to the foliar applied cyhalofop-butyl and pyribenzoxim herbicides, herbicidal response, the rate of absorption, translocation and metabolism were studied. Among 148 individuals of Echinochloa species collected from 41 sampling sites in Korea which were classified into 7 geographical regions, based on morphological characteristics of plant and seed type, 46 lines were used for further studies. From them, E. crus-galli var. praticola collected from Hwanggan and E. crus-galli var. crus-galli collected from Namyangju were selected as the most susceptible species to cyhalofop-butyl and pyribenzoxim, respectively. Meanwhile, E. oryzicola(from Cheju) and E. crus-galli var. crus-galli(from Asan) were selected as tolerant species to cyhalofop-butyl and pyribenzoxim, respectively. Application of radio-labelled herbicides on the 1st leaf to both susceptible and tolerant Echinochloa species exhibited that the applied $^{14}C$-Cyhalofop-butyl and $^{14}C$-pyribenzoxim were more easily absorbed and translocated into stem tissues than root. Absorption of $^{14}C$-Cyhalofop-butyl increased rapidly at 1 h after application and reached the maximum at 12 h after application. However, the absorption rate of $^{14}C$-pyribenzoxim was not changed. Two metabolites from cyhalofop-butyl-treated plants and one metabolite from pyribenzoxim-treated plants were separated by TLC. The amount of metabolite 1 in cyhalofop-butyl-treated tolerant species was significantly higher than that in the susceptible one, suggesting differences in detoxification ability between susceptible and tolerant species.

• Toxicological Research
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• v.22 no.1
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• pp.1-8
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• 2006

The primary metabolism of pyribenzoxim was studied in rat liver microsomes in order to identify the cytochrome P450 (CYP) isoform(s) and esterases involved in the metabolism of pyribenzoxim. Chemical inhibition using CYP isoform-selective inhibitors such as ${\alpha}$-naphthoflavone, tolbutamide, quinine, chlorzoxazone, troleandomycin, and undecynoic acid indicated that CYP1A and CYP2D are responsible for the oxidative metabolism of pyribenzoxim. And inhibitory studies using eserine, bis-nitrophenol phosphate, dibucaine, and mercuric chloride indicated pyribenzoxim hydrolysis involved in microsomal carboxylesterases containing an SH group (cysteine) at the active center.

• The Korean Journal of Pesticide Science
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• v.9 no.2
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• pp.153-158
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• 2005

Safening activities of optically active ${\alpha}$-methylbenzylphenylureas on crop injury of rice (Oryza sativa L., cv. Tsukinohikari, japonica) caused by bensulfuron-methyl (methyl 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoate) and pyribenzoxim (benzophenone o-[2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzoyl]oxime) were investigated. Some derivatives of the optically active compounds exhibited strong safening activity against growth inhibition of rice by bensulfuron-methyl. Out of the derivatives tested, (S)-2,3-diCl and (S)-2-F-4-Me derivatives showed greater relieving activity than that of dymuron. In addition, the stress relieving activity was also obtained when they were applied at 4 days after bensulfuron-methyl treatment. On the other hand, crop injury caused by pyribenzoxim was relieved by about 95% with (S)-2-F-4-Me derivative in shoots and roots of rice seedlings.

• Bulletin of the Korean Chemical Society
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• v.23 no.7
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• pp.1042-1044
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• 2002

• Journal of Applied Biological Chemistry
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• v.43 no.1
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• pp.49-53
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• 2000

The in vitro metabolism of a new herbicide pyribenzoxim, {benzophenone O-[2,6-bis[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzoyl]oxime} was studied using rice, barnyardgrass and rat liver microsomes. No metabolism of pyribenzoxim was observed with rice and barnyardgrass microsomes though the cvtochrome P450 was active, which was evidenced by the metabolism of cinnamic acid. With rat liver microsomes, four metabolites (M1, M2, M3, and M4) were produced while parent compound decreased. M1 and M2 were from the hydrolysis reactions and NADPH-dependent metabolites were M3 and M4 (major metabolite) which were hydroxylated by cytochrome P450. They were identified as bispyribac-sodium (M1), benzophenone oxime (M2), {benzophenone O-[2,6-bis[(5-hydroxy-4,6-dimethoxy-2-pyrimidinyl)oxy]-benzoyl]oxime}(M3), and {benzophenone O-[2[(5-hydroxy-4,6-dimethoxy-2l-pyrimidinyl)6-(4,.6dimethoxy-2-pyrimidinyl)oxy]benzoyl]oxime} (M4) through LC/MS/MS analyses. Based on the results obtained metabolic map of pyribenzoxim is proposed.

• Journal of Applied Biological Chemistry
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• v.43 no.2
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• pp.112-114
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• 2000

• Korean Journal of Weed Science
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• v.18 no.3
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• pp.197-204
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• 1998

This study was conducted to determine the activity of ALS, content of endogenous free amino acids and fatty acids affected by herbicide mixture of cyhalofop-butyl, pyribenzoxim and pyrazosulfuron-ethyl. $I_{50}$ values (concentration required for 50% inhibition of ALS activity) of pyribenzoxim herbicide on the activity of ALS in Echinochloa crus-galli and Cyperus serotinus in vitro were recorded at 4${\times}$100 nM and 5${\times}$10 nM, respectively, while $I_{50}$ values of pyrazosulfuron against E crus-galli and C. serotinus were 4.5${\times}$10 nM and 4${\times}$10 nM, respectively, and the mixture of two herbicides showed additive effect on ALS activity at the low application rate, and independent effect at the high application rates of two herbicides. The inhibition rates of the three herbicides mixture treatment on the three branch-chain amino acids such as valine, leucine and isoleucine were 74.6%, 66.6% and 57.9% in C. serotinus and 36.6% 51.1% and 48.1% in E. crus-galli, respectively. A little bit higher inhibitory effect on the three branch-chain amino acids in C. serotinus and E. crus-galli seedlings was observed in two herbicide mixture of pyribenzoxim with pyrazosulfuron than three herbicide mixture of cyhalofop with pyribenzoxim and pyrazosulfuron. The interaction among three herbicides showed non-antagonism on the amounts of endogenous free amino acids.

• Korean Journal of Weed Science
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• v.18 no.4
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• pp.304-313
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• 1998

Foliar retention of pyribenzoxim (1% EC) was measured using the fluorescent dye rhodamine B, and related to efficacy and phytotoxicity to barnyardgarss (Echinochloa crusgalli) and rice (Oryza sativa cv. Chucheong), respectively. Effects of nozzle types (8002E flat-fan and disk-type), addition of adjuvant, variation of herbicide concentration or spray volume were compared. In barnyardgrass, foliar retention of pyribenzoxim at a recommended condition (application rate : 30g ai/ha, spray volume : 1000 L/ha) was 2.3 to 2.7 or 1.4 to $1.5{\mu}g$ ai/g fresh foliage when sprayed using the disk-type nozzle with or without adjuvant, respectively, and 0.6 to 0.7 or 0.3 to $0.5{\mu}g$ ai/g fresh foliage when sprayed using the flat-fan nozzle with or without adjuvant, respectively. The slope of increase in foliar retention was 1.0 to 1.8 when application rates increased from 10 to 60g ai/ha at 1000 L/ha, while that was 1.6 to 2.4 when spray volume increased from 330 to 2000 L/ha at $30{\mu}g$ ai/L concentration. Foliar retention of pyribenzoxim had a close relationship with herbicidal activity; regardless of spray conditions, retention to provide 90% control was about $0.8{\mu}g$ ai/g fresh foliage, and below this retention amount, efficacy decreased almost linearly. In rice, foliar retention at the recommended condition was 1.9 to 2.3 or 1.2 to $1.3{\mu}g$ ai/g fresh foliage when sprayed using the disk-type nozzle with or without adjuvant, respectively, and 0.6 to 0.9 or $0.3{\mu}g$ ai/g fresh foliage when sprayed using the flat-fan nozzle with or without adjuvant, respectively. The slope of increase in foliar retention was 1.0 to 2.8 when application rates increased from 30 to 120g ai/ha at 1000 L/ha, while that was 1.3 to 4.4 when spray volume increased from 1000 to 4000 L/ha at $30{\mu}g$ ai/L concentration. Despite the great difference in retention, rice phytotoxicity was not observed in any of these spray conditions, suggesting retention differences within 4-fold increase of application rate or spray volume do not affect rice safety. When pyribenzoxim 1EC was sprayed in tank-mix with several other commercial pesticide formulations, its retention to rice foliage tended to increase by 30 to 50%.

• The Korean Journal of Pesticide Science
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• v.4 no.4
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• pp.81-86
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• 2000

The objective was to develop herbicides for liquorice (Glycyrrhiza uralensis), one of most important ingredients of herbal medicine in Korea. Soil-applied herbicides, pendimethalin at 1,585 g a.i. $ha^{-1}$, simazine at 1,000 g a.i. $ha^{-1}$, alachlor at 5 g a.i. $ha^{-1}$, metolachlor at 1,600 g a.i. $ha^{-1}$, and ethalfluralin at 1,050 g a.i. $ha^{-1}$ provided greater control of hairy crabgrass and barnyardgrass (> 60%) but less control of Abutilon avicennae and Fagopyrum esculentum under growth chamber conditions. Of tested soil-applied herbicides, pendimethalin and simazine showed slight injury to liquorice (<17%). In the field experiment conducted in Chunchon, pendimethalin and simazine provided greater control of weeds: total fresh weight of weeds in control plots was 187 g $m^{-2}$, while those in both herbicides-treated plots were nil. Fresh weights of liquorice seedlings in pendimethalin- and simazine-applied plots, however, were not different from those in control plots. Foliar-applied herbicides, such as dicamba at 964 g a.i. $ha^{-1}$, 2,4-D at 280 g a.i. $ha^{-1}$, mecoprop at 2,500 g a.i. $ha^{-1}$, flazasulfuron at 75 g a.i. $ha^{-1}$, imazaquin at 800 g a.i. $ha^{-1}$, bentazon at 1,600 g a.i. $ha^{-1}$, and pyribenzoxim at 30 g a.i. $ha^{-1}$ reduced the growth of liquorice seedlings and provided moderate to total damage. Overall results show that pendimethalin and simazine appears to be effective herbicide candidates for liquorice.