Synlett 2019; 30(01): 59-62
DOI: 10.1055/s-0037-1610341
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Conformationally Locked and C-Linked Analogues of Imidazole-Based Ketene Dithioacetal Fungicides

Julien Gagnepain
,
Stephane Jeanmart
,
Damien Bonvalot
,
Olivier Jacob
,
Clemens Lamberth*
Syngenta Crop Protection AG, Chemical Research, Schaffhauserstrasse 101, 4332 Stein, Switzerland   Email: clemens.lamberth@syngenta.com
› Author Affiliations
Further Information

Publication History

Received: 25 September 2018

Accepted after revision: 05 November 2018

Publication Date:
03 December 2018 (online)

Abstract

First examples with the unknown tricyclic 4,8b-dihydro-3aH-indeno[1,2-d][1,3]dithiole ring system have been prepared. Also, imidazoles linked in ring position 5 to a ketene dithioacetal and 1,3-dithiane derivatives with an exocyclic cyano- and imidazole-substituted C–C double bond are completely new. All these compounds are either conformationally locked, C-linked or six-ring analogues of the antifungal agent luliconazole. Synthesis and fungicidal activity of these sterol biosynthesis inhibitors are reported.

Supporting Information

 
  • References and Notes

  • 1 Peyton LR, Gallagher S, Hashemzadeh M. Drugs Today 2015; 51: 705
  • 2 Heeres J, Meerpoel L, Lewi P. Molecules 2010; 15: 4129
  • 3 Worthington P. In Bioactive Heterocyclic Compound Classes: Agrochemicals . Lamberth C, Dinges J. Wiley-VCH; Weinheim: 2012: 129
  • 4 Kuck K.-H, Stenzel K, Vors J.-P. In Modern Crop Protection Compounds . Krämer W, Schirmer U, Jeschke P, Witschel M. Wiley-VCH; Weinheim: 2012: 761
  • 5 Niwano Y, Ohmi T, Seo A, Kodama H, Koga H, Sakai A. Curr. Med. Chem. Anti-Infect. Agents 2003; 2: 147
  • 6 Niwano Y, Ohmi T, Seo A, Kodama H, Kanai K. Recent Res. Dev. Antimicrob. Agents Chemother. 2000; 4: 81
  • 7 Niwano Y, Seo A, Kanai K, Hamaguchi H, Uchida K, Yamaguchi H. Antimicrob. Agents Chemother. 1994; 38: 2204
  • 8 Scher RK, Nakamura N, Tavakkol A. Mycoses 2014; 57: 389
  • 9 Uchida K, Nishiyama Y, Tanaka T, Yamaguchi H. Int. J. Antimicrob. Agents 2003; 21: 234
  • 10 Koga H, Nanjoh Y, Kaneda H, Yamaguchi H, Tsuboi R. Antimicrob. Agents Chemther. 2012; 56: 3138
  • 11 Jeanmart S, Gagnepain J, Maity P, Lamberth C, Cederbaum F, Rajan R, Jacob O, Blum M, Bieri S. Bioorg. Med. Chem. 2018; 26: 2009
  • 12 Levesque G, Tabak G, Outurquin F, Gressier JC. Bull. Soc. Chim. Fr. 1976; 1156
  • 13 Murphy Kessabi F, Beaudegnies R, Quaranta L, Lamberth C. Tetrahedron Lett. 2016; 57: 5511
  • 14 Castilla J, Risquez R, Higaki K, Nanba E, Ohno K, Suzuki Y, Diaz Y, Ortiz Mellet C, Garcia Fernandez JM, Castillon S. Eur. J. Med. Chem. 2015; 90: 258
  • 15 Shing TK. M, Wong AW. H, Li H, Liu ZF, Chan PK. S. Org. Biomol. Chem. 2014; 12: 9439
  • 16 Nayak A, Chandra G, Hwang I, Kim K, Hou X, Kim HO, Sahu PK, Roy KK, Yoo J, Lee Y, Cui M, Choi S, Moss SM, Phan K, Gao Z.-G, Ha H, Jacobson KA, Jeong LS. J. Med. Chem. 2014; 57: 1344
  • 17 Brant MG, Wulff JE. Org. Lett. 2012; 14: 5876
  • 18 Dixit SS, Upadhayaya RS, Chattopadhyaya J. Org. Biomol. Chem. 2012; 10: 6121
  • 19 Yale HL, Spitzmiller ER. J. Heterocycl. Chem. 1978; 15: 1373
  • 20 Sharma AK, Subramani AV, Gorman CB. Tetrahedron 2007; 63: 389
  • 21 Rackelmann N, Matter H, Englert H, Follmann M, Maier T, Weston J, Arndt P, Heyse W, Mertsch K, Wirth K, Bialy L. J. Med. Chem. 2016; 59: 8812
  • 22 Zhang R, Dong J, Xu Y, Hua W, Wen N, You Q. Eur. J. Med. Chem. 2009; 44: 3771
  • 23 Litzinger EA, Martasek P, Roman LJ, Silverman RB. Bioorg. Med. Chem. 2006; 14: 3185
  • 24 De la Hoz A, Blasco H, Diaz-Ortiz A, Elguero J, Foces-Foces C, Moreno A, Sanchez-Migallon A, Valiente G. New. J. Chem. 2002; 26: 926
  • 25 Gagnepain J, Bonvalot D, Jeanmart S. WO 2015011194, 2015
  • 26 Dulcevscaia GM, Kravtsov VC, Macaev FZ, Duca GG, Stingachi EP, Pogrebnoi SI, Boldescu VV, Clapco SF, Tiurina JP, Deseatnic-Ciloci AA, Lipkowski J, Liu S.-X, Decurtins S, Baca SG. Polyhedron 2013; 52: 106
  • 27 de S Fonseca T, Lima LD, de Oliveira MC. F, de Lemos TL. G, Zampieri D, Molinari F, de Mattos MC. Eur. J. Org. Chem. 2018; 2110
  • 28 Bonvalot D, Jeanmart S, Gagnepain J. WO2015003991, 2015
  • 29 Matulic-Adamic J, Watanabe KA. Korean J. Med. Chem. 1991; 1: 54
  • 30 Przybyla D, Nubbemeyer U. Eur. J. Org. Chem. 2017; 695
  • 31 De Figueiredo RM, Coudray L, Dubois J. Org. Biomol. Chem. 2007; 5: 3299
  • 32 Enoua GC, Uray G, Stadlbauer W. J. Heterocycl. Chem. 2012; 49: 1415
  • 33 Chenevert R, Desjardins M. Can. J. Chem. 1994; 72: 2312
  • 34 Rios-Lombardia N, Busto E, Gotor-Fernandez V, Gotor V. Eur. J. Org. Chem. 2010; 484