Synthesis and fungicidal activity of tubulin polymerisation promoters. Part 3: Imidazoles

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 1, 2013, Pages 127-134

  Lamberth, Clemens ^a   Dumeunier, Raphael ^a   Trah, Stephan ^a   Wendeborn, Sebastian ^a   Godwin, Jeremy ^a   Schneiter, Peter ^a   Corran, Andy ^b  

^a SYNGENTA CROP PROTECTION AG   (Switzerland)

^b JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE   (United Kingdom)

Author keywords

Crop protection; Fungicide; Heterocycle; Imidazole; Tubulin

Indexed keywords

(4 CHLORO PHENYL) 5 (2,4,6 TRIFLUORO PHENYL) 1H IMIDAZOLE; (4 CHLORO PHENYL) [1 (2,4,6 TRIFLUORO PHENYL) METH (E) YLIDENE]AMINE; 1 (4 CHLORO PHENYL) 2 METHYL 5 (2,4,6 TRIFLUORO PHENYL) 1H IMIDAZOLE; 1 [2 CHLORO 3 (2,6 DIFLUORO 4 METHOXY PHENYL) 5 METHYL 3H IMIDAZOL 4 YL] 4 METHYL PIPERIDINE; 1 [3 (2,6 DIFLUORO 4 METHOXY PHENYL) 5 METHYL 3H IMIDAZOL 4 YL] 4 METHYL PIPERIDINE; 2 BROMO 1 (4 CHLORO PHENYL) 5 (2,4,6 TRIFLUORO PHENYL) 1H IMIDAZOLE; IMIDAZOLE DERIVATIVE; PACLITAXEL; TUBULIN; UNCLASSIFIED DRUG;

ALTERNARIA; ALTERNARIA SOLANI; ARTICLE; BOTRYTIS CINEREA; CELL DISRUPTION; CONTROLLED STUDY; DRUG SYNTHESIS; FUNGICIDAL ACTIVITY; FUNGUS; GLOMERELLA GRAMINICOLA; MICROTUBULE ASSEMBLY; MOLECULAR DYNAMICS; NONHUMAN; STRUCTURE ACTIVITY RELATION; UNCINULA NECATOR;

ALTERNARIA; ASCOMYCOTA; BOTRYTIS; FUNGICIDES, INDUSTRIAL; IMIDAZOLES; PLANT DISEASES; PLANT PROTEINS; PLANTS; TUBULIN; TUBULIN MODULATORS;

ALTERNARIA SOLANI; BOTRYOTINIA FUCKELIANA; BOTRYTIS; ERYSIPHE NECATOR; LYCOPERSICON ESCULENTUM; MYCOSPHAERELLA GRAMINICOLA; SOLANUM TUBEROSUM; TRITICUM AESTIVUM;

EID: 84870914512     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.10.052     Document Type: Article

References (26)

1. Part 2 C. Lamberth, S. Trah, S. Wendeborn, R. Dumeunier, M. Courbot, J. Godwin, and P. Schneiter Bioorg. Med. Chem. 20 2012 2803
2. H. Walter C. Lamberth, J. Dinges, Bioactive Heterocyclic Compound Classes-Agrochemicals 2012 Wiley-VCH Weinheim 175 193
3. J. Rheinheimer, H. Rieck, and P.-Y. Coqueron W. Krämer, U. Schirmer, P. Jeschke, M. Witschel, Modern Crop Protection Compounds 2012 Wiley-VCH Weinheim 627 645
4. A. Suty-Heinze, R. Dunkel, U. Krieg, and H. Rieck H.W. Dehne, H.B. Deising, U. Gisi, K.-H. Kuck, P.-E. Russell, H. Leyr, Modern Fungicides and Antifungal Compounds VI 2011 DPG Braunschweig 69 73
5. G. Stammler, H.D. Brix, A. Glaettli, M. Semar, and U. Schoefl Proceed. Int. Plant Protect. Congr. Glasgow 1 2007 40
6. T. Veloukas, and G.S. Karaoglanidis Pest Manag. Sci. 68 2012 858
7. M. Semar, D. Strobel, S. Strathmann, and U. Groeger H.W. Dehne, H.B. Deising, U. Gisi, K.-H. Kuck, P.-E. Russell, H. Leyr, Modern Fungicides and Antifungal Compounds VI 2011 DPG Braunschweig 63 68
8. H. Nagahori, H. Yoshino, Y. Tomigahara, N. Isobe, H. Kaneko, and I. Nakatsuka J. Agric. Food Chem. 48 2000 5754
9. T.L. Harp, J.R. Godwin, G. Scalliet, H. Walter, A.D. Stalker, D.L. Bartlett, and D.J. Ranner Aspects Appl. Biol. 106 2011 113
10. Y. Yanase, Y. Yoshikawa, J. Kishi, and H. Katsuta H. Ohkawa, H. Miyagawa, P.W. Lee, Pesticide Chemistry 2007 Wiley-VCH Weinheim 295
11. F. Montel, C. Lamberth, and P.M.J. Jung Tetrahedron 64 2008 6372
12. Zeun, R.; Cederbaum, F.; Oostendorp, M. WO 2007/141010 (Syngenta). Chem. Abstr. 2007, 148, 25706.
13. P.J. Crowley, C. Lamberth, U. Müller, S. Wendeborn, K. Nebel, J. Williams, O.-A. Sageot, N. Carter, T. Mathie, H.-J. Kempf, J. Godwin, P. Schneiter, and M.R. Dobler Pest Manage. Sci. 66 2010 178
14. P.J. Crowley, C. Lamberth, U. Müller, S. Wendeborn, O.-A. Sageot, J. Williams, and A. Bartovic Tetrahedron Lett. 51 2010 2652
15. Finkelstein, B. L. WO 2009/158257 (Du Pont). Chem. Abstr. 2009, 152, 97356.
16. Gypser, A.; Grote, T.; Schwoegler, A.; Rheinheimer, J.; Schieweck, F.; Tormo i Blasco, J.; Rose, I.; Schäfer, P.; Gewehr, M.; Grammenos, W.; Müller, B.; Ammermann, E.; Strathmann, S.; Lorenz, G.; Stierl, R. WO 2003/043993 (BASF). Chem. Abstr. 2003, 138, 401748.
17. Bereznak, J. F.; Stevenson, T. M.; Sharpe, P. L.; Taggi, A. E. WO 2007/149448 (Du Pont). Chem. Abstr. 2007, 148, 100635.
18. C. Almansa, J. Alfon, A.F. de Arriba, F.L. Cavalcanti, I. Escamilla, L.A. Gomez, A. Miralles, R. Soliva, J. Bartroli, E. Carceller, M. Merlos, and J. Garcia-Rafanell J. Med. Chem. 46 2003 3463
19. R. Soliva, C. Almansa, S.G. Kalko, F.J. Luque, and M. Orozco J. Med. Chem. 46 2003 1372
20. D. van Leusen, and A.M. van Leusen Org. React. 57 2001 417
21. A.M. van Leusen, J. Wildeman, and O.H. Oldenziel J. Org. Chem. 42 1977 1153
22. R. ten Have, M. Huisman, A. Meetsma, and A.M. van Leusen Tetrahedron 53 1997 11355
23. Dumeunier, R.; Lamberth, C.; Trah, S. WO 2009/127615 (Syngenta). Chem. Abstr. 2009, 151, 491123.
24. B.C. Ranu, S.S. Dey, and A. Hajra Tetrahedron 58 2002 2529
25. Pawar, V. G.; De Borggraeve, W. M.; Robeyns, K.; Van Meervelt, L; Compernolle, F.; Hoornaert, G. Tetrahedron Lett. 2006, 47, 5451.
26. Dumeunier, R.; Lamberth, C.; Trah, S. WO 2010/102866 (Syngenta). Chem. Abstr. 2010, 153, 431359.