Synthesis of Indole Derivatives and Their Evaluation against Root Knot Nematode Meloidogyne incognita

Page: [759 - 767] Pages: 9

  • * (Excluding Mailing and Handling)

Abstract

Eight new 2-(1H-indol-3-yl)-N-(aryl)-2-oxoacetamide amine based indole derivatives were synthesized. Microanalytical data, 1HNMR, 13CNMR, FT-IR and XRD were used to characterize the synthesized derivatives. The indole derivatives had also been screened for their nematicidal activity against root-knot nematode Meloidogyne incognita. Chlorine substituted indole derivatives had shown significant nematicidal activity comparative to other indole derivatives.

Keywords: Indole, oxalyl chloride, amine, indole derivatives, nematicidal activity, Meloidogyne incognita, hatching, mortality.

Graphical Abstract

[1]
Hiroya, K.; Itoh, S.; Sakamoto, T. J. Org. Chem., 2004, 69, 1126-1136.
[2]
Gribble, G.W. J. Chem. Soc., Perkin Trans. 1, 2000, 2, 1045-1075.
[3]
Kumar, A.; Sharma, S.; Maurya, R.A. Tetrahedron Lett., 2009, 50, 5937-5940.
[4]
Mane, A.; Lohar, T.; Salunkhe, R. Tetrahedron Lett., 2016, 57, 2341-2346.
[5]
Shelke, S.M.; Bhosale, S.H.; Mahadik, K.R. Der Pharma Chem, 2010, 2, 169-177.
[6]
Rajaraman, D.; Sundararajan, G.; Loganath, N.K.; Krishnasamy, K. J. Mol. Struct., 2016, 1127, 597-610.
[7]
Akhaja, T.N.; Raval, J.P. Eur. J. Med. Chem., 2011, 46, 5573-5579.
[8]
Vidhya, N.; Thirumurugan, P.; Noorulla, K.; Perumal, P. Bioorg. Med. Chem. Lett., 2010, 20, 5054-5061.
[9]
Li, J.T.; Lin, Z.P. Ultrason. Sonochem., 2008, 15, 265-268.
[10]
Singh, N.; Agarwal, R.C.; Singh, C.P. Int. J. Pharm. Sci. Drug Res., 2013, 5, 14-17.
[11]
Radwan, M.A.; Raqab, E.A.; Shabry, N.M.; El-Shenawy, S.M. Bioorg. Med. Chem., 2007, 15, 3832-3841.
[12]
Rossiter, S.; Folkes, L.K.; Wardman, P. Bioorg. Med. Chem. Lett., 2002, 12, 2523-2526.
[13]
Aboul-Enien, H.Y.; Kruk, I.; Lichszteld, K.; Michalska, T.; Kladna, A.; Marczynski, S.; Olgen, S. Luminenscence, 2004, 19, 1-7.
[14]
Marchand, P.; Antoine, M.; Le Baut, G.; Czech, M.; Baasner, S.; Günther, E. Bioorg. Med. Chem., 2009, 17, 6715-6727.
[15]
Gul, W.; Hamman, M.T. Life Sci., 2005, 78, 442-453.
[16]
Kohmoto, S.; Kashman, Y.; McConnell, O.J.; Rinehart, K.L.; Wright, A.; Koehn, F. J. Org. Chem., 1988, 53, 3116-3118.
[17]
Rinehart, K.L.; Kobayashi, J.; Harbour, G.C.; Gilmore, J. Mascal. M.; Holt, T.G.; Shield, L.S.; Lafargue, F.; Eudistomins, A.-Q. J. Am. Chem. Soc., 1987, 109, 3378-3387.
[18]
Bobzin, S.C.; Faulkner, D.J. J. Org. Chem., 1991, 56, 4403-4407.
[19]
Sato, H.; Tsuda, M.; Watanabe, K.; Kobayashi, J. Tetrahdron, 1998, 54, 8687-8690.
[20]
Scuotto, M.; Abdelnabi, R.; Collarile, S.; Schiraldi, C.; Leen, D.; Massa, A.; Ferla, S.; Brancale, A.; Leyssen, P.; Neyts, J.; Filosa, R. Bioorg. Med. Chem. Lett., 2017, 25, 327-337.
[21]
Che, Z.; Zhang, S.; Shao, Y.; Fan, L.; Xu, H.; Yu, X.; Zhi, X.; Yao, X.; Zhang, R. J. Agric. Food Chem., 2013, 61, 5696-5705.
[22]
Truong, N.M.; Ngyuen, C.N.; Abad, P. Adv. Bot. Res., 2015, 73, 293-324.
[23]
McCarter, J.P. Molecular approaches toward resistance to plant parasitic nematode.In: Cell Biology of Plant Nematode Parasitism; Berg, R.H.; Taylor, C.G., Eds.; Springer-Verlag Press: Berlin, 2009, pp. 83-113.
[24]
Waele, D.D.; Davide, R.G. Int. Net. Imp. Banana Plantain. Parc. Sci. Agropolis, 1998, 2, 1-4.
[25]
Wang, G.L.; Chen, X.; Chang, Y.N.; Dan, D.; Li, Z.; Xu, X.Y. Chin. Chem. Lett., 2015, 3471, 1-5.
[26]
Gamliel, A.; Austerweil, M.; Kritzman, G. Crop Prot., 2000, 19, 847-853.
[27]
Vannacci, G.; Gullino, M.L. Acta Hortic., 2000, (532), 79-87.
[28]
Tjmaos, E.C.; Polymnia, P.A.; Tjamos, S.E. Crop Prot., 2000, 19, 843-846.
[29]
Haydock, P.P.J.; Woods, S.R.; Grove, I.G. Chemical control of nematodes. In: Plant Nematology., Perry. R.N.; Moens, M.; Ed; CABI, Wallinfgord, CT. 2006, pp 392-408.
[30]
Yudelman, M.; Ratta, A.; Nygaard, D. Eur. J. Chem., 1998, 42, 55-60.
[31]
Li, X-J.; Zheng, K.; Wang, L-D.; Li, Y-T.; Wu, Z-Y.; Yan, C-W. J. Inorg. Biochem., 2013, 128, 97-107.
[32]
Altomare, A.; Cascarano, G.; Giacovazzo, G.; Gualardi, A. J. Appl. Cryst., 1993, 26, 343-350.
[33]
Sheldrick, G.M. SHELXTL-PC Version 5.05 Structure determination programs; Ana Instruments Inc: Madison, WI, 1995.
[34]
Tocco, G.; Eloh, K.; Onnis, V.; Sasanelli, N.; Caboni, P. Ind. Crops Prod., 2017, 110, 94-102.