• The Korean Journal of Pesticide Science
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• v.12 no.4
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• pp.315-322
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• 2008

In this study, a simple, effective, and sensitive method has been developed for the quantitative residue analysis of cyhalofop-butyl and its metabolite cyhalofop acid in water and soil when kept under laboratory conditions. The content of cyholofop-butyl and cyhalofop acid in water and soil was analyzed by first purifying the compounds through liquid-liquid extraction and partitioning followed by Silica gel (adsorption) chromatography. Upon the completion of the purification step the residual levels were monitored through high-performance liquid chromatography (HPLC) using a UV absorbance detector. The recoveries of cyhalofop-butyl from three replicates spiked at two different concentrations ranged from 82.5 to 100.0% and from 66.7 to 97.9% in water and soil, respectively. The limit of detection and minimum detection level of cyhalofop-butyl in water and soil was 0.02 ppm and 10 ng, respectively. The recoveries of cyhalofop acid ranged from 80.7 to 104.8% in water and from 76.9 to 98.1 % in soil. The limit of detection of cyhalofop acid was 0.005 ppm in water and 0.01 ppm in soil, while the minimum detection level was 2 ng both in water and soil. The half-live of cyhalofop-butyl was 4.14 and 6.6 days in water and soil, respectively. The method was successfully applied to evaluate cyhalofop-butyl residues in water and soil applied aj. 30% emulsion, oil in water (EW) product.

• 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.

• Korean Journal of Weed Science
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• v.14 no.3
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• pp.223-227
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• 1994

Basis for differential response of rice and E. crus-galli to cyhalofop-butyl ester (R-butyl 2-(4-(4-cyano-2-fluoro-phenoxy)phenoxy)propionate) was anatomically compared. Cell division in the growing point of E. crus-galli was severely inhibited by the herbicide, leading to malformation and irregular arrangement of cells. The inhibitory symptom of rice by cyhalofop-butyl ester appeared to be very similiar to that of E. crus-galli although its injury was negligible in rice when applied at the rate of 180ppm.

• Korean Journal of Weed Science
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• v.14 no.2
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• pp.94-100
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• 1994

This experiment was conducted to determine selective mechanism of cyhalofop-butyl ester ((((R-butyl 2-(4-(4-cyano-2-fluorophenoxy) phenoxy) propionate)) between rice and Echinochloa crus-galli. 100ppm of cyhalofop-butyl ester inhibited over 90% of seedling growth of E. crus-galli when applied at 3 leaf stage and complete inhibition was observed at 180ppm applied at the 4 leaf stage, but rice(Chucheongbyeo) was not inhibited by cyhalofop-butyl ester even at 230ppm, regardless of its growth stages(3, 4, 5 and 6 leaf stages). Cyhalofop-butyl ester applied through stem at 10 and 50ppm moved most rapidly to the meristem and resulted in the highest injury on plant height, root length and fresh weight of E. crus-galli. compared with root or leaf application. Seedlings of rice and E. crus-galli at 3 or 4 leaf stage were dipped in 180ppm of cyhalofop-butyl ester solution for 1 minute and aboveground parts of E. crus-galli and rice were removed immediataly after dipping treatment. Regrowth of E. crus-galli was inhibited by the herbicide by 41.7%, but no inhibition was observed in rice. Further, content of chlorophyll reduced to 18.7% of the untreated control, showing appearence of almost being killed, but no effect on chlorophyll content of rice was observed.

• Korean Journal of Weed Science
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• v.17 no.2
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• pp.185-191
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• 1997

This experiment was conducted to determine the selective mechanism of cyhalofop-butyl ester on uptake, traslocation, and metabolism of the herbicide in both rice and Echinochloa crus-galli. Uptake and translocation of $^{14}C$-cyhalofop-butyl ester was higher in E. crus-galli than rice when treated to shoot. $^{14}C$-uptake by root of E. crus-galli increased rapidly at 30 minute after treatment and reached the maximum at 12 hoots after treatment. After that, uptake was leveled off. Uptake pattern in rice root was not significantly affected by the duration of herbicide treatment. In E. crus-galli, the absorbed $^{14}C$-cyhalofop-butyl ester seemed to be rapidly metabolized into free acid and the content of changed free acid was higher than rice.

• Korean Journal of Weed Science
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• v.18 no.2
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• pp.154-160
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• 1998

This study was conducted to develop a foliar applied herbicide mixture covering wide spectrum weeds in dry direct seeded rice. Uniform precision central composite design(UPCCD) was employed to evaluate the effect of herbicide mixture among cyhalofop-butyl(cyhalofop), bispyribenzoxim and pyrazosulfuron-ethyl(pyrazosulfuron) having different weed control spectrum and to determine the best application rates of the three herbicide mixtures. The partial additive effect was observed in the mixture of cyhalofop and bispyribenzoxim with pyrazosulfron against Echinochloa crus-galli Beauv var crus-galli L., attributed to the negative interaction between cyhalofop and bispyribenzoxim system. Additive effect was observed in the mixture of bispyribenzoxim and pyrazosulfuron against Cyperus serotinus R. and Aneilema keisak H. but cyhalofop had no effect on these weeds. The most appropriate rate of the mixture of cyhalofop with bispyribenzoxim and pyrazosulfuron was 100 : 12 : 10g ai/ha exhibiting $ED_{90}$ against three weeds such as E. crus-galli, C. serotinus and A. keisak.

• Korean Journal of Weed Science
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• v.17 no.2
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• pp.192-198
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• 1997

This experiment was carried out to determine selectivity of herbicide cyhalofop-butyl ester on enzyme activity, biosynthesis of fatty acid and protein between rice and Echinochloa crus-galli. Activity of the acetyl-CoA carboxylase(ACCase) was inhibited greater in E. crus-galli than in rice by the treatment of cyhalofop-butyl ester. The ACCase activity in E. crus-galli was observed with $I_{50}$ at 1-2ppm of cyhalofop-butyl ester, while in rice only at above 10ppm. Cyhalofop-butyl ester also inhibited the biosynthesis of fatty acid by 61% of palmitic acid, 54% of linoleic acid and 41% of linolenic acid in E. crux-galli. In contrast, no significant difference of fatty acid content was observed in rice at 5DAT as compared with the untreated control. Protein patterns of rice between the herbicide treatment and the untreated control were not significantly different, but in E. crus-galli, 3 protein spots were disappeared in between 29KD and 45KD.

• Applied Biological Chemistry
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• v.38 no.5
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• pp.440-446
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• 1995

In order to select the proper formulation of newly developed herbicide Cyhalofop-butyl{n-butyl-(R)-2-[4-(2-fluro-4-cyanophenoxy)phenoxy]propionte} to Echino-chloacrus-galli(L)P. Beaw. several formulations were made and tested by biological assay. Weed control of wettable powder formulated with two adjuvants on E. crus-galli showed higher effect as compared with the formulation made without adjuvants. Higher concentration of adjuvants resulted in higher absorption and higher weed control on E. crus-galli. However, adhesional force of wettable powder applied to leaf surface was not positively correlated to the amount of herbicide absorption. The weeding effect and amount of herbicide absorbed on E. crus-galli were higher by emulsifiable concentrateformulations with different HLB and non ionic surfactants as compared with wettable powder formulations. The higher adhesional force and higher absorption of herbicide on E. crus-galli were obtained from microemulsion than the others. Granulization of the herbicide with appropriate adjuvants in a form of resurfacing on the submerged water gave rise to a good weeding effect and believed to be a possible promising formulation.

• Weed & Turfgrass Science
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• v.6 no.4
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• pp.345-349
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• 2017

Herbicides are important weed control tools for increasing crop yields and the efficiency of crop production. As the use of herbicides increases, the occurrrence of herbicide-resistant weeds has been an increaing problem. In Korea, since the first occurrence of acetolactate synthase (ALS) inhibitor resistant Monochoria korsakowii was reported in the Seosan reclaimed paddy field in 1998, resistance has been reported in 14 weed species, including Echinochola spp. and their populations are gradually increasing. The objective of this study is to investigate the nationwide occurrence of ALS and Acetyl-CoA Carboylase inhibitor resistant Echinochloa spp. in Korea. In 2013, 2014, and 2015, we collected 594 accessions of Echinochloa spp. in Korean rice fields except for Jeonnam and Chungbuk provinces. They were then treated with the recommended rates of penoxsulam and cyhalofop-butyl. We harvested seeds from 45 accessions of E. oryzicola in the case of cyhalofop-butyl treatment. Also, 44 and 46 accessions of E. oryzicola and E. crus-galli survived and their seeds were harvested after penoxsulam treatment. Twenty accessions of E. oryzicola survived from both herbicides inferring possible multiple resistance. Two accessions out of 20 inferred from possible multiple resistance survived after cyhalofop-butyl treatment at a dose of $500ga.i.ha^{-1}$. Seeds of herbicide resistant populations will be provided and utilized for further research.

• Weed & Turfgrass Science
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• v.7 no.2
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• pp.166-169
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• 2018

Repeated use of ACCase inhibiting herbicides for a long time has resulted in increases of resistant Echinochloa oryzicola populations in paddy fields in middle west area of Korea. This study aims to investigate current status of herbicide resistant E. oryzicola in Gyeongsangnam-do, in which there is less information about herbicide resistance. For resistance frequency and dose-response study, seeds from 100 individual plants of E. oryzicola in Gyeongsangnam-do were collected and tested with cyhalofop-butyl. Seven percent of plants from Gyeongsangnam-do was resistant at a recommended rate of cyhalofop-butyl. $GR_{50}$ values (herbicide rates required to reduce plant growth 50%) for one representative resistant populations and five susceptible populations were $738g\;a.i.\;ha^{-1}$ and 66-234 (average 147)$g\;a.i.\;ha^{-1}$, respectively, indicating average 5 times difference in resistance. Although lower rate of frequency of herbicide resistance in Gyeongsangnam-do than in Jeollabuk-do, increases of herbicide resistance are expected in this area because of increases of direct seeded rice fields and increases of dependence on a specific herbicide. Therefore, it is necessary to monitor herbicide resistance regularly and conduct integrated herbicide resistance management in this area.