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Original Articles

Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita

ORCID Icon, , &
Pages 194-200 | Received 13 Jun 2019, Accepted 26 Aug 2019, Published online: 09 Sep 2019

References

  • Baldacci-Cresp, F.; Maucourt, M.; Deborde, C.; Pierre, O.; Moing, A.; Brouquisse, R.; Favery, B.; Frendo, P. Maturation of Nematode-Induced Galls in Medicago truncatula Is Related to Water Status and Primary Metabolism Modifications. Plant Sci. 2015, 232, 77–85. DOI: 10.1016/j.plantsci.2014.12.019.
  • Perry, R. N.; Moens, M. Introduction to Plant-Parasitic Nematodes; Modes of Parasitism. In Genomics and Molecular Genetics of Plant-Nematode Interactions; Jones, J.; Gheysen, G.; Fenoll, C., Eds.; Springer Netherlands: Dordrecht, 2011; pp 3–20.
  • Opperman, C. H.; Chang, S. Plant-Parasitic Nematode Acetylcholinesterase Inhibition by Carbamate and Organophosphate Nematicides. J. Nematol. 1990, 22, 481–488. DOI: 10.1002/jez.1402560114.
  • Kyprianou, M. Commission Decision of 20 September 2007 concerning the non-inclusion of 1,3-dichloropropene in Annex I to Council Directive 91/414/EEC and the withdrawal of Authorisations for Plant Protection Products Containing that Substance (Notified Under Document Number C (2007) 4281). In Official Journal of the European Union, 25/09/2007 ed.; European Community: Brussels, 2007; Vol. 50, p 11.
  • Lahm, G. P.; Desaeger, J.; Smith, B. K.; Pahutski, T. F.; Rivera, M. A.; Meloro, T.; Kucharczyk, R.; Lett, R. M.; Daly, A.; Smith, B. T.; et al. The Discovery of Fluazaindolizine: A New Product for the Control of Plant Parasitic Nematodes. Bioorg. Med. Chem. Lett. 2017, 27, 1572–1575. DOI: 10.1016/j.bmcl.2017.02.029.
  • Faske, T. R.; Hurd, K. Sensitivity of Meloidogyne incognita and Rotylenchulus Reniformis to Fluopyram. J. Nematol. 2015, 47, 316–321. DOI: 10.1007/s00264-009-0778-1.
  • Oka, Y.; Shuker, S.; Tkachi, N. Systemic Nematicidal Activity of Fluensulfone against the Root-Knot Nematode Meloidogyne incognita on Pepper. Pest Manag. Sci. 2012, 68, 268–275. DOI: 10.1002/ps.2256.
  • Scott, K. A.; Njardarson, J. T. Analysis of US FDA-Approved Drugs Containing Sulfur Atoms. Top. Curr. Chem. 2018, 376, 1–34. DOI: 10.1007/s41061-018-0184-5.
  • Devendar, P.; Yang, G.-F. Sulfur-Containing Agrochemicals. Top. Curr. Chem. 2017, 375, 1–44. DOI: 10.1007/s41061-017-0169-9.
  • Sondhi, S. M.; Rani, R.; Gupta, P. P.; Agrawal, S. K.; Saxena, A. K. Synthesis, Anticancer, and Anti-Inflammatory Activity Evaluation of Methanesulfonamide and Amidine Derivatives of 3,4-Diaryl-2-Imino-4-Thiazolines. Mol. Divers. 2009, 13, 357–366. DOI: 10.1007/s11030-009-9125-0.
  • Bandgar, B. P.; Adsul, L. K.; Chavan, H. V.; Shringare, S. N.; Korbad, B. L.; Jalde, S. S.; Lonikar, S. V.; Nile, S. H.; Shirfule, A. L. Synthesis, Biological Evaluation, and Molecular Docking of N-{3-[3-(9-Methyl-9H-Carbazol-3-yl)-Acryloyl]-Phenyl}-Benzamide/Amide Derivatives as Xanthine Oxidase and Tyrosinase Inhibitors. Bioorg. Med. Chem. 2012, 20, 5649–5657. DOI: 10.1016/j.bmc.2012.07.001.
  • Gaumont, A.-C.; Gulea, M.; Levillain, J. Overview of the Chemistry of 2-Thiazolines. Chem. Rev. 2009, 109, 1371–1401. DOI: 10.1021/cr800189z.
  • Han, F. S.; Osajima, H.; Cheung, M.; Tokuyama, H.; Fukuyama, T. Novel Structural Motifs Consisting of Chiral Thiazolines: Synthesis, Molecular Recognition, and Anticancer Activity. Chem. Eur. J. 2007, 13, 3026–3038. DOI: 10.1002/chem.200601446.
  • Jain, A.; Utley, L.; Parr, T. R.; Zabawa, T.; Pucci, M. J. Tebipenem, the First Oral Carbapenem Antibiotic. Expert Rev. Anti-Infect. Ther. 2018, 16, 513–522. DOI: 10.1080/14787210.2018.1496821.
  • Hong, J.; Luesch, H. Largazole: From Discovery to Broad-Spectrum Therapy. Nat. Prod. Rep. 2012, 29, 449–456. DOI: 10.1039/c2np00066k.
  • Kato, K.; Shirasaka, Y.; Kuraoka, E.; Kikuchi, A.; Iguchi, M.; Suzuki, H.; Shibasaki, S.; Kurosawa, T.; Tamai, I. Intestinal Absorption Mechanism of Tebipenem Pivoxil, a Novel Oral Carbapenem: Involvement of Human OATP Family in Apical Membrane Transport. Mol. Pharmaceutics 2010, 7, 1747–1756. DOI: 10.1021/mp100130b.
  • Almaliti, J.; Al-Hamashi, A. A.; Negmeldin, A. T.; Hanigan, C. L.; Perera, L.; Pflum, M. K. H.; Casero, R. A.; Tillekeratne, L. M. V. Largazole Analogues Embodying Radical Changes in the Depsipeptide Ring: Development of a More Selective and Highly Potent Analogue. J. Med. Chem. 2016, 59, 10642–10660. DOI: 10.1021/acs.jmedchem.6b01271.
  • Watanabe, Y.; Mihara, J.; Yamazaki, H.; Otsu, Y.; Shibuya, K.; Shimojo, E. Thiazolylfluorobutenoic Acids and Nematocides Containing Them. JP2005008567A, Jan 13, 2005.
  • Wang, G.; Chen, X.; Chang, Y.; Du, D.; Li, Z.; Xu, X. Synthesis of 1,2,3-Benzotriazin-4-One Derivatives Containing Spirocyclic Indoline-2-One Moieties and Their Nematicidal Evaluation. Chin. Chem. Lett. 2015, 26, 1502–1506. DOI: 10.1016/j.cclet.2015.10.024.
  • Wang, G.; Chen, X.; Deng, Y.; Li, Z.; Xu, X. Synthesis and Nematicidal Activities of 1,2,3-Benzotriazin-4-One Derivatives against Meloidogyne incognita. J. Agric. Food Chem. 2015, 63, 6883–6889. DOI: 10.1021/acs.jafc.5b01762.
  • Chang, Y.; Zhang, J.; Chen, X.; Li, Z.; Xu, X. Synthesis and Nematicidal Activities of 1,2,3-Benzotriazin-4-One Derivatives Containing Thiourea and Acylthiourea against Meloidogyne incognita. Bioorg. Med. Chem. Lett. 2017, 27, 2641–2644. DOI: 10.1016/j.bmcl.2016.12.065.
  • Rigterink, R. H. Insecticidal use of S-((4-Oxo-1,2,3-Benzotriazin-3(4H)-yl)Methyl) Phosphorothioates and Phosphorodithioates. US3551562A, Dec 29, 1970.
  • Hosler, J. F.; Hardy, W. B. 3-Trichloromethylthio-1,2,3-Benzotriazin-4-One and Its Use as a Nematocide. US2935445, May 3, 1960.
  • Lin, Y.; Luo, P.; Zheng, Q.; Liu, Y.; Sang, X.; Ding, Q. Efficient Construction of C-S and C-N Bonds via Metal-Free Reductive Coupling of N-Tosylhydrazones with Benzo[d]Thiazole-2-Thiol. RSC Adv. 2014, 4, 16855–16863. DOI: 10.1039/C4RA00590B.
  • Crystallographic Data Have Been Deposited with the Accession Number CCDC 1918103 at the Cambridge Crystallographic Data Centre, Cambridge, UK, 2019. www.ccdc.cam.ac.uk/conts/retrieving.html.
  • Moens, M.; Perry, R. N.; Starr, J. L. Meloidogyne Species – A Diverse Group of Novel and Important Plant Parasites. In Root-Knot Nematodes; Perry, R. N., Ed.; CABI Publishing: Wallingford, UK, 2009; Vol. 1, pp 1–17.
  • Fernandez, C.; Rodriguez-Kabana, R.; Warrior, P.; Kloepper, J. W. Induced Soil Suppressiveness to a Root-Knot Nematode Species by a Nematicide. Biol. Control 2001, 22, 103–114. DOI: 10.1006/bcon.2001.0961.
  • Twomey, U.; Rolfe, R. N.; Warrior, P.; Perry, R. N. Effects of the Biological Nematicide, DiTera, on Movement and Sensory Responses of Second Stage Juveniles of Globodera Rostochiensis, and Stylet Activity of G. rostochiensis and Fourth Stage Juveniles of Ditylenchus Dipsaci. Nematology 2002, 4, 909–915. DOI: 10.1163/156854102321122520.
  • Clark, A. S.; Deans, B.; Stevens, M. F. G.; Tisdale, M. J.; Wheelhouse, R. T.; Denny, B. J.; Hartley, J. A. Antitumor Imidazotetrazines. 32.1 Synthesis of Novel Imidazotetrazinones and Related Bicyclic Heterocycles to Probe the Mode of Action of the Antitumor Drug Temozolomide. J. Med. Chem. 1995, 38, 1493–1504. DOI: 10.1021/jm00009a010.

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