• Bulletin of the Korean Chemical Society
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• v.33 no.8
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• pp.2627-2634
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• 2012

Strobilurins are one of the most important classes of agricultural fungicides. To discover new strobilurin derivatives with high activity against resistant pathogens, a series of novel ${\beta}$-methoxyacrylate analogues were designed and synthesized by integrating substituted pyrimidine with a strobilurin pharmacophore. The compounds were confirmed and characterized by infrared, $^1H$ nuclear magnetic resonance, elemental analysis and mass spectroscopy. The bioassays indicated that most of the compounds (1a-1h) exhibited potent antifungal activities against Colletotrichum orbiculare, Botrytis cinerea Pers and Phytophthora capsici Leonian at the concentration of 50 ${\mu}g/mL$. Exhilaratingly, compound 1d (R=3-trifluoromethylphenyl) showed better antifungal activity against all the tested fungi than the commercial strobilurin fungicide azoxystrobin.

• Bulletin of the Korean Chemical Society
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• v.31 no.11
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• pp.3341-3347
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• 2010

A series of oxazolidinone-based strobilurin analogues were efficiently synthesized by the reaction of 3-(2-bromomethylphenyl) oxazolidin-2-one with 1-substituted phenyl-2H-pyrazolin-3-one. Their structures were confirmed and characterized by $^1H$-NMR, $^{13}C$-NMR, elemental analysis, and mass spectroscopy. In addition, the crystal structure of the target compound 3-(2-((1-phenyl-2H-pyrazol-3-yloxy)methyl)phenyl) oxazolidin-2-one was determined by single crystal X-ray diffraction. The bioassay results of these compounds indicated that some of the oxazolidin-2-one derivatives containing N-substituted phenyl 2H-pyrazol ring exhibited potential in vivo fungicidal activities against M. grisea at the dosage of $1\;g\;L^{-1}$.

• Research in Plant Disease
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• v.28 no.3
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• pp.122-131
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• 2022

Colletotrichum acutatum s. lat. 20JDS8 sensitive and 20CDJ6 resistant to pylaclostrobin were used to investigate the cross-resistance with fungicides belonging to the strobilurins and the characteristics of fungicidal controlling activities with different mechanisms against the isolate resistant to the fungicide. The resistant isolate of 20CDJ6 also showed the resistance to azoxystrobin, trifloxystrobin, and kresoxim-methyl, suggesting that there is a cross-resistance relationship. All fungicides with different action mechanisms inhibited mycelial growth of both susceptible and resistant isolates of C. acutatum s. lat., but their disease control effects in fruits were different according to the fungicides. The disease control effect of isopyrazam against 20JDS8 and 20CDJ6 was very low, and fluazinam showed a control effect of 91.9% and 88.1% against 20JDS8 and 20CDJ6 only when it was treated before inoculation by spraying spore suspensions on pepper fruits without wounds. Tebuconazole and prochloraz effectively inhibited not only the mycelial growth of 20JDS8 and 20CDJ6 on potato dextrose agar medium, but also disease incidence in red pepper fruits. As a result of this study, C. acutatum s. lat. 20CDJ6 resistant to pyraclostrobin showed cross-resistance with other strobilurin fungicides. In addition, we think that fluazinam, tebuconazole, and prochloraz can be recommended as alternative fungicides for the control of red-pepper pyranthracnose pathogens resistant pyraclostrobin. However, fluazinam can be effective only if it is treated protectively before the occurrence of the disease.

• Bulletin of the Korean Chemical Society
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• v.30 no.7
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• pp.1475-1480
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• 2009

Methoxyiminoacetate and methoxyiminoacetamide derivatives possessing 2,2-dichlorovinyl side chains, have been synthesized and their biological activities against six representative plant fungal pathogens have been evaluated. Five substances in this series (3a, 4a, 3b, 3d, and 4d) were found to exhibit potent fungicidal activities compared to those of the commercially available fungicides, azoxystrobin and fenarimol.

• Bulletin of the Korean Chemical Society
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• v.23 no.9
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• pp.1199-1214
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• 2002

• The Korean Journal of Pesticide Science
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• v.9 no.2
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• pp.132-139
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• 2005

New ${\beta}$-methoxyacrylate derivatives 1-4 having thio-enol side chain were prepared and subjected to in vivo screening for fungicidal activity against phytopathogenic fungi and many of them showed good fungicidal activities against especially rice blast and wheat leaf rust at 100 ppm.

• The Korean Journal of Pesticide Science
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• v.18 no.3
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• pp.161-167
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• 2014

This study was conducted to investigate the resistance of Botrytis cinerea to azoxystrobin, which belongs to strobilurin fungicides. The sensitivity of B. cinerea isolates, which were collected from infected pepper, strawberry, cucumber and tomato by a single spore isolation, to the fungicide was tested through a agar dilution method on PDA amended with fungicides and $100{\mu}g\;mL^{-1}$ of salicylhydroxamic acid (SHAM). All isolates of B. cinerea tested in this study were classified as a sensitive and a resistant group by $1.0{\mu}g\;mL^{-1}$ of $EC_{50}$ value to azoxystrobin. While the sensitive isolates accounted for 46.5% of B. cinerea population, the resistant ones did for 53.5%. According to the regions isolating B. cinerea, the highest isolation frequency was showed as 81.1% in Chungnam among the all. Among 4 host plants as pepper, strawberry, cucumber and tomato, the highest isolation frequency was obtained in strawberry, while the lowest was done in pepper. The isolate resistant to azoxystrobin showed the cross resistance to other fungicides included into strobilurins as kresoxim-methyl and trifloxystrobin. In spite of an excellent efficacy of strobilurins, it should be taken care to use them in the field, because of the high risk in the fields.

• Weed & Turfgrass Science
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• v.6 no.2
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• pp.151-156
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• 2017

Summer patch is the most serious disease at turfgrass field or golf course established with Kentucky bluegrass during high temperature season in Korea. Nevertheless, chemicals for the summer patch control are not yet registered in Korea. We isolated the pathogens from the turfgrass showing typical summer patch symptoms and identified as Magnaporthiopsis poae by using the internal transcribed spacer ITS1 and ITS4 sequences of rDNA. The inhibition rates of the pathogen were investigated for 10 fungicides. As results, the pathogen growth was suppressed when chemicals concentration increased and negatively correlated with incubation period with the chemicals. In triazole group, all chemicals (metconazole, myclobutanil, propiconazole and tebuconazole) treated showed the inhibition rates by 100%. Thiophanate-methyl showed the next highest inhibition effect against a summer patch pathogen. In strobilurin group, pyraclostrobin was the highest suppression effect compared with azoxystrobin and trifloxystrobin. Inhibition effect of fludioxonil and fluxapyroxad on pathogen was similar to the trifloxystrobin. Based on the results, triazole and carboxamide groups are strongly recommended due to the highest inhibition effect on the summer patch pathogen, Magnaporthiopsis poae.

• Research in Plant Disease
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• v.18 no.1
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• pp.10-16
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• 2012

This study was conducted to examine the effects of the seeding rate on the disease incidence of sharp eyespot(Rhizoctonia cerealis) on three different varieties and to select effective chemicals to control the disease. When the seeds were sown twice as many as the recommendation, the disease incidence increased by approximately 13%. However, the susceptible variety 'Jopummil' alone showed the significantly enhanced disease incidence at a two-fold seeding rate. Two chemicals such as Hexaconazole EC and Tebuconazole EC highly inhibited the fungal growth on agar medium. However, two strobilurin fungicides such as Pyraclostrobin EC and Trifloxystrobin SC were relatively weak. The fungicides tested displayed the similar in vivo antifungal activities as in vitro activities. Hexaconazole EC and Tebuconazole EC showed the strongest both protective and curative activities and the protective activities of the chemicals were generally higher than the curative activities. Hexaconazole EC and Tebuconazole EC controlled the disease by 64% and 73%, respectively, and the two chemicals reduced the disease by 45% and 39%, respectively, when they were applied one day after pathogen inoculation. These results indicate that both Hexaconazole EC and Tebuconazole EC could be used to control sharp eyespot on wheat.

• Bulletin of the Korean Chemical Society
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• v.25 no.10
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• pp.1513-1520
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• 2004

We investigate a series of synthesized ${\beta}$-methoxyacrylate analogues for their 3D QSAR & HQSAR against Magnaporthe grisea (Rice Blast Disease). We perform the three-dimensional Quantitative Structure-Activity Relationship (3D-QSAR) studies, using the comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) procedure. In addition, we carry out a two-dimensional Quantitative Structure-Activity Relationship (2D-QSAR) study, using the Hologram QSAR (HQSAR). We perform these studies, using 53 compounds as a training set and 10 compounds as a test set. The predictive QSAR models have conventional $r^2$ values of 0.955 at CoMFA, 0.917 at CoMSIA, and 0.910 at HQSAR respectively; similarly, we obtain cross-validated coefficient $q^2$ values of 0.822 at CoMFA, 0.763 at CoMSIA, and 0.816 at HQSAR, respectively. From these studies, the CoMFA model performs better than the CoMSIA model.