• Bulletin of the Korean Chemical Society
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• 제33권8호
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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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• 제31권11호
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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 $1\;g\;L^{-1}$.

• Bulletin of the Korean Chemical Society
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• 제30권7호
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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.

• 농약과학회지
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• 제9권2호
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• pp.132-139
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• 2005

천연 살균활성 물질인 strobilurin으로부터 유래된 ${\beta}$-methoxyacrylate 계열 화합물들은 천연물 자체보다 높은 살균활성 및 안정성을 보이는 것으로 알려졌으며 실제로 다수의 화합물이 우수한 농업용 살균제로 개발 시판되어 지고 있다. 본 연구에서는 보다 나은 살균제를 개발하기 위한 일환으로 티오엔을 곁가지를 가진 새로운 ${\beta}$-methoxyacrylate 계열 화합물을 고안하고 합성하였으며 이들의 살균활성을 6가지 균주에 대하여 in vivo 활성검색을 수행하였다. 새로이 합성된 화합물들은 선택적으로 벼도열병균 및 밀녹병균에 대하여 우수한 살균활성을 보였으며 특히 1b, 1c, 1g 화합물은 100 ppm 농도에서 벼도열병균과 밀녹병균에 대하여 100% 살균효과를 보였다.