• Title, Summary, Keyword: strobilurin

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Design, Synthesis and Antifungal Activities of Novel Strobilurin Derivatives Containing Pyrimidine Moieties

  • Zhang, Xiang;Gao, Yong-Xin;Liu, Hui-Jun;Guo, Bao-Yuan;Wang, Hui-Li
    • 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.

Synthesis, Crystal Structure and Fungicidal Activities of New Type Oxazolidinone-Based Strobilurin Analogues

  • Li, Yuhao;Liu, Rui;Yan, Zhangwei;Zhang, Xiangning;Zhu, Hongjun
    • 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 $1\;g\;L^{-1}$.

Screening of Fungicide Resistance of Cucumber Powdery Mildew Pathogen, Sphaerotheca fusca in Gyeonggi Province (경기 지역 오이 흰가루병균(Sphaerotheca fusca)의 살균제 저항성 검정)

  • Kim, Jin-Young;Hong, Sun-Sung;Lim, Jae-Wook;Park, Kyeong-Yeol;Kim, Hong-Gi
    • Research in Plant Disease
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    • v.14 no.2
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    • pp.95-101
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    • 2008
  • Fungicide resistance of cucumber powdery mildew was screened among the pathogens isolated from diseased plants in main cucumber productuion areas in Gyeonggi Province. Each fungicide from different activity group for the control of powdery mildew were sprayed on cucumber leaves according to application concentration. Each conidia mixed with sterilized water isolated of pathogens were transferred on the cucumber leaf disks treated with each fungicide. At 7 to 9 days after inoculation of pathogen, disease severity was recorded under the microscope. Most of pathogen isolates showed moderate resistance to difenoconazole belonged to DMI group fungicide while some isolates from Osan were resistant even $300{\mu}g/ml$. Isolates from Pyeongtaek, Osan and Yongin area also showed moderate resistance to fenarimol while one isolate showed resistant to fenarimol even $300{\mu}g/ml$. Most of isolates from Pyeongtaek, Osan and Yongin showed highly resistant to azoxystrobin belonged to strobilurin group fungicide. Standard sensitive isolates the minimum inhibition concentration(MIC) value for azoxystrobin showed $200{\mu}g/ml$ while resistance isolates showed above $2000{\mu}g/ml$. Resistant isloates also showed cross resistance among strobilurin group fungicides and low control efficacy in the field test. These results suggest that treatment of strobilurin fungicides should be reduced for the control of powdery mildew.

Synthesis and SAR of Methoxyiminoacetate and Methoxyiminoacetamide Derivatives as Strobilurin Analogues

  • Hwang, In-Cheon;Kim, Joo-Kyung;Kim, Hyung-Ho;Kyung, Suk-Hun
    • 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.

Investigation of Fungicide Response of Streptomyces spp. Isolated from Rhizosphere in Zoysiagrass (한국 잔디 근권에서 분리된 Streptomyces spp.의 살균제에 대한 반응조사)

  • Lee, Jung Han;Min, Gyu Young;Jeon, Chang Wook;Choi, Su Min;Shim, Gyu Yul;Kwak, Youn-Sig
    • The Korean Journal of Pesticide Science
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    • v.19 no.1
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    • pp.54-63
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    • 2015
  • Streptomyces spp. isolated from turfgrass rhizosphere and tested for their response to large-patch control fungicides. The tested fungicides were actually used in golf course or turfgrass cultivation to prevent large-patch disease. Tolerance to 3 triazole group of the strains was the highest to the PR fungicide, and following the SR fungicide, whereas the isolated strains were no tolerance to HR fungicide. Tolerances to three kind of Strobilurin group were similar for the all of the tested Streptomyces spp.. Growth and sporulation of the all strain was normal in CB and AP fungicide treatments. However no spore formulated in double concentration. Strains, tolerance to acetanilide fungicides, appeared that KT fungicide tolerance was higher than MK fungicide. The selected strains showed strong tolerance against AT fungicide but have no tolerance to ATR fungicides. In conclusion, the bacterial strains showed tolerance against 1 carbamate, 1 organophosphate and 1 cyanopyrrole group, while have no tolerance against two mixture formulations (1 Quinone + Strobilurin and 1 Imidazole + Triazole).

Synthesis and fungicidal activity of new ${\beta}$-methoxyacrylate derivatives having thio-enol side chain (티오엔을 곁가지를 가진 메톡시아크릴레이트 화합물의 합성 및 살균활성 연구)

  • Lee, Hyeon-Kyu;Kim, Ji-A;Choi, Eun-Bok;Park, Chwang-Siek;Choi, Gyung-Ja
    • 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.

Residual Patterns of Strobilurin Fungicides in Korean Melon under Plastic Film House Condition (Strobilurin계 살균제의 시설재배 참외 중 잔류 양상)

  • Park, Eun-Jeong;Lee, Ju-Hee;Kim, Tae-Hwa;Kim, Jang-Eok
    • Korean Journal of Environmental Agriculture
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    • v.28 no.3
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    • pp.281-288
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    • 2009
  • The strobilurin fungicides, azoxystrobin and kresoxim-methyl, were investigated to know the biological half-lives and dissipation patterns in Korean melon under plastic film house condition. Used pesticides for field application were 20% azoxystrobin of suspension concentrate and 47% kresoxim-methyl of water dispersible granule. Two pesticides were sprayed at recommended and double dose rate. Pesticide residues in Korean melon were analyzed until 14 days after application. The azoxystrobin was analyzed by HPLC equipped with UV detector after cleanup with florisil glass column. Initial residue concentrations of azoxystrobin in Korean melon at recommended and double dose rate were 0.09 mg/kg and 0.14 mg/kg, respectively. Those were less than 0.2 mg/kg maximum residue limit of Korean melon established by KFDA. The biological half-lives of azoxystrobin in Korean melon were 4.7 days at recommended dose rate and 7.8 days at double dose rate. Initial concentrations of kresoxim-methyl which was analyzed by GLC-ECD in Korean melon at recommended and double dose rate were 0.10 mg/kg and 0.23 mg/kg, respectively. Those were less than 1.0 mg/kg, MRL. The biological half-lives of kresoxim-methyl in Korean melon were 4.1 days at recommended dose rate and 4.8 days at double dose rate. The residue amounts of both pesticide was lower than MRL and biological half-lives were not so long. Because the weight of Korean melon under plastic film house condition was fast increased during cultivation.

Investigation of Fungicides Inhibitory Effect of on Summer Patch Disease, Caused by Magnaporthiopsis poae, in Kentucky bluegrass (여름잎마름병(Summer patch) 병원균에 대한 살균제의 억제효과 조사)

  • Lee, Jung Han;Shim, Gyu Yul;Kim, Jeong Ho;Jeon, Chang Wook;Kwak, Youn-Sig
    • 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.

Monitoring for the Resistance of Strobilurin Fungicide Against Botrytis cinerea Causing Gray Mold Disease (Strobilurin계 살균제에 대한 잿빛곰팡이병균 Botrytis cinerea의 저항성 검정)

  • Kim, Ah Hyeong;Kim, Seon Bo;Han, Ki Don;Kim, Heung Tae
    • 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.