Haloalkyl Group

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正明 山谷 - One of the best experts on this subject based on the ideXlab platform.

Thomas J Slanec - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis and antifungal activity of 3‐aryl‐1,2,4‐triazin‐6‐one derivatives
    Pest management science, 2014
    Co-Authors: Owen W John, Michael Sullenberger, Michael R. Loso, Kevin G. Meyer, Thomas J Slanec
    Abstract:

    BACKGROUND As a result of resistance development in many plant-pathogenic fungi to agricultural fungicides, there is an ongoing need to discover novel antifungal chemistries to help sustain efficient crop production. A fungicide screening program identified 3-phenyl-1-(2,2,2-trifluoroethyl)-1,2,4-triazin-6(1H)-one (5) as a promising new starting point for further activity optimization. A series of analogs were designed, prepared and evaluated in growth inhibition assays using four plant-pathogenic fungi. RESULTS Thirty nine analogs (compounds 5 to 43) were prepared to explore structure–activity relationships at R1 and R2, and all targeted structures were characterized by 1H NMR and MS. All compounds were in vitro tested against three ascomycetes [Leptosphaeria nodorum, Magnaporthe grisea and Zymoseptoria tritici (syn. Mycosphaerella graminicola)] and one basidiomycete (Ustilago maydis) pathogen. When R2 was trifluoroethyl, fungicidal activity was enhanced by a single electron-withdrawing substitution, such as Br, Cl and CF3 in the 3-position at R1 (compounds 9, 10 and 12), of which the 3-bromo compound (10) was the most active (EC50 = 0.08, averaged across four pathogens). More subtle activity improvement was found by addition of a second halogen substituent in the 4-position, with the 3-Br-4-F analog (20) being the most active against the commercially important cereal pathogen Z. tritici. Replacement of the R2 Haloalkyl Group with benzyl, alkyl (e.g. n-butyl, i-butyl, n-pentyl) and, particularly, CH2-cycloalkyls (e.g. CH2-cyclopropyl, CH2-cyclobutyl) resulted in further activity enhancements against the ascomycete fungi, but was either neutral or detrimental to activity against U. maydis. One of the most active compounds in this series (41) gave control of Z. tritici, with an EC50 of 0.005 ppm, comparable with that of the commercial strobilurin fungicide azoxystrobin (EC50 0.002 ppm). CONCLUSIONS The present work demonstrated that the 3-phenyl-1,2,4-triazin-6-ones are a novel series of compounds with highly compelling levels of antifungal activity against agriculturally relevant plant-pathogenic fungi. © 2014 Society of Chemical Industry

和弘 土田 - One of the best experts on this subject based on the ideXlab platform.

Owen W John - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis and antifungal activity of 3‐aryl‐1,2,4‐triazin‐6‐one derivatives
    Pest management science, 2014
    Co-Authors: Owen W John, Michael Sullenberger, Michael R. Loso, Kevin G. Meyer, Thomas J Slanec
    Abstract:

    BACKGROUND As a result of resistance development in many plant-pathogenic fungi to agricultural fungicides, there is an ongoing need to discover novel antifungal chemistries to help sustain efficient crop production. A fungicide screening program identified 3-phenyl-1-(2,2,2-trifluoroethyl)-1,2,4-triazin-6(1H)-one (5) as a promising new starting point for further activity optimization. A series of analogs were designed, prepared and evaluated in growth inhibition assays using four plant-pathogenic fungi. RESULTS Thirty nine analogs (compounds 5 to 43) were prepared to explore structure–activity relationships at R1 and R2, and all targeted structures were characterized by 1H NMR and MS. All compounds were in vitro tested against three ascomycetes [Leptosphaeria nodorum, Magnaporthe grisea and Zymoseptoria tritici (syn. Mycosphaerella graminicola)] and one basidiomycete (Ustilago maydis) pathogen. When R2 was trifluoroethyl, fungicidal activity was enhanced by a single electron-withdrawing substitution, such as Br, Cl and CF3 in the 3-position at R1 (compounds 9, 10 and 12), of which the 3-bromo compound (10) was the most active (EC50 = 0.08, averaged across four pathogens). More subtle activity improvement was found by addition of a second halogen substituent in the 4-position, with the 3-Br-4-F analog (20) being the most active against the commercially important cereal pathogen Z. tritici. Replacement of the R2 Haloalkyl Group with benzyl, alkyl (e.g. n-butyl, i-butyl, n-pentyl) and, particularly, CH2-cycloalkyls (e.g. CH2-cyclopropyl, CH2-cyclobutyl) resulted in further activity enhancements against the ascomycete fungi, but was either neutral or detrimental to activity against U. maydis. One of the most active compounds in this series (41) gave control of Z. tritici, with an EC50 of 0.005 ppm, comparable with that of the commercial strobilurin fungicide azoxystrobin (EC50 0.002 ppm). CONCLUSIONS The present work demonstrated that the 3-phenyl-1,2,4-triazin-6-ones are a novel series of compounds with highly compelling levels of antifungal activity against agriculturally relevant plant-pathogenic fungi. © 2014 Society of Chemical Industry

Kevin G. Meyer - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis and antifungal activity of 3‐aryl‐1,2,4‐triazin‐6‐one derivatives
    Pest management science, 2014
    Co-Authors: Owen W John, Michael Sullenberger, Michael R. Loso, Kevin G. Meyer, Thomas J Slanec
    Abstract:

    BACKGROUND As a result of resistance development in many plant-pathogenic fungi to agricultural fungicides, there is an ongoing need to discover novel antifungal chemistries to help sustain efficient crop production. A fungicide screening program identified 3-phenyl-1-(2,2,2-trifluoroethyl)-1,2,4-triazin-6(1H)-one (5) as a promising new starting point for further activity optimization. A series of analogs were designed, prepared and evaluated in growth inhibition assays using four plant-pathogenic fungi. RESULTS Thirty nine analogs (compounds 5 to 43) were prepared to explore structure–activity relationships at R1 and R2, and all targeted structures were characterized by 1H NMR and MS. All compounds were in vitro tested against three ascomycetes [Leptosphaeria nodorum, Magnaporthe grisea and Zymoseptoria tritici (syn. Mycosphaerella graminicola)] and one basidiomycete (Ustilago maydis) pathogen. When R2 was trifluoroethyl, fungicidal activity was enhanced by a single electron-withdrawing substitution, such as Br, Cl and CF3 in the 3-position at R1 (compounds 9, 10 and 12), of which the 3-bromo compound (10) was the most active (EC50 = 0.08, averaged across four pathogens). More subtle activity improvement was found by addition of a second halogen substituent in the 4-position, with the 3-Br-4-F analog (20) being the most active against the commercially important cereal pathogen Z. tritici. Replacement of the R2 Haloalkyl Group with benzyl, alkyl (e.g. n-butyl, i-butyl, n-pentyl) and, particularly, CH2-cycloalkyls (e.g. CH2-cyclopropyl, CH2-cyclobutyl) resulted in further activity enhancements against the ascomycete fungi, but was either neutral or detrimental to activity against U. maydis. One of the most active compounds in this series (41) gave control of Z. tritici, with an EC50 of 0.005 ppm, comparable with that of the commercial strobilurin fungicide azoxystrobin (EC50 0.002 ppm). CONCLUSIONS The present work demonstrated that the 3-phenyl-1,2,4-triazin-6-ones are a novel series of compounds with highly compelling levels of antifungal activity against agriculturally relevant plant-pathogenic fungi. © 2014 Society of Chemical Industry