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Construction and Characterization of 3,7-Dichloro-N-(2,6-Diethylphenyl)-N-(2-Propoxyethyl)Quinolone-8-Carboxamide: A Potential Novel Pesticide Compound

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Chemistry of Heterocyclic Compounds Aims and scope

A novel compound, 3,7-dichloro-N-(2,6-diethylphenyl)-N-(2-propoxyethyl)quinoline-8-carboxamide was synthesized by splicing together a chloro-substituted quinoline moiety found in quinclorac (a selective herbicide) and a substituted amide moiety found in pretilachlor (another selective herbicide) using the active substructure splicing method. The chemical structure of this compound was characterized by 1H, 13C NMR, FTIR, high-resolution mass spectra and X-ray diffraction analysis. Pesticide potency (herbicidal and fungicidal activity) of this compound was evaluated. This compound displayed excellent control efficiency against Echinochloa crusgalli and also showed good fungicidal in vitro activity against Phytophthora capsici, Phytophthora sojae, and Phytophthora infestans.

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References

  1. Deng, X. L.; Zhou, Y.; Zheng, W. N.; Bai, L. Y.; Zhou, X. M. Int. J. Environ. Res. Public Health 2018, 15, 1680.

    PubMed Central  Google Scholar 

  2. Tuti, M. D.; Das, T. K.; Sairam, R. K.; Annapurna, K.; Singh, S. B. Int. J. Pest Manage. 2015, 61, 17.

    CAS  Google Scholar 

  3. Khaliq, A.; Matloob, A.; Tanweer, A.; Khan, M. B. Nat. Prod. Res. 2012, 26, 1156.

    CAS  PubMed  Google Scholar 

  4. Busi, R.; Nguyen, N. K.; Chauhan, B. S.; Vidotto, F.; Tabacchie, M.; Powles, S. B. Pest Manage. Sci. 2017, 73, 71.

    CAS  Google Scholar 

  5. Vagapova, L. I.; Burilov, A. R.; Gazizov, A. S.; Voronina, J. K.; Litvinov, I. A.; Mahrous, E. M.; Virieux, D.; Pirat, J.-L.; Matylitskii, K. V.; Pudovik, M. A. Chem. Heterocycl. Compd. 2020, 56, 542. [Khim. Geterotsikl. Soedin. 2020, 56, 542.]

  6. Golmohammadzadeh, S.; Gherekhloo, J.; Rojano-Delgado, A. M.; Osuna-Ruíz, M. D.; Kamkar, B.; Ghaderi-Far, F.; Prado, D. R. Agronomy 2019, 9, 377.

    CAS  Google Scholar 

  7. Stroganova, T. A.; Vasilin, V. K.; Krapivin, G. D.; Strelkov, V. D.; Dyadyuchenko, L. V. Chem. Heterocycl. Compd. 2016, 52, 45. [Khim. Geterotsikl. Soedin. 2016, 52, 45.]

  8. Gromachevskaya, E. V.; Kaigorodova, E. A.; Konyushkin, L. D. Chem. Heterocycl. Compd. 2017, 53, 545. [Khim. Geterotsikl. Soedin. 2017, 53, 545.]

  9. Ou, J. J.; Fritz, A. K.; Stahlman, P. W.; Currie, R. S. Jugulam, M. Weed Sci. 2019, 67, 16.

    Google Scholar 

  10. Margaritopoulou, T.; Tani, E.; Chachalis, D.; Travlos, I. Agriculture 2018, 8, 17.

    Google Scholar 

  11. LeClere, S.; Wu, C.; Westra, P.; Sammons, R. D. Proc. Natl. Acad. Sci. U. S. A. 2018, 115, E2911.

    CAS  PubMed Central  PubMed  Google Scholar 

  12. Busi, R.; Powles, S. B.; Beckie, H. J.; Renton, M. Pest Manage. Sci. 2019, 76, 487.

    Google Scholar 

  13. Bai, S.; Zhang, F. W.; Li, Z. R.; Wang, H. Z.; Wang, Q.; Wang, J. X.; Liu, W. T.; Bai, L. Y. Pestic. Biochem. Phys. 2019, 155, 8.

    CAS  Google Scholar 

  14. Menck, B.-H.; Kiessling, U.; Unglaub, W.; Rosebrock, H. DE Patent 3422215.

  15. Dahabiyeh, L. A.; Bustanji, Y.; Taha, M. O. Chem. Biol. Drug Des. 2019, 93, 787.

    CAS  PubMed  Google Scholar 

  16. Peng, Q.; Han, H.; Yang, X.; Yang, L.; Yu, Q.; Powles, S. B. Rice Sci. 2019, 26, 300.

    Google Scholar 

  17. Geng, R. M.; Luo, C. G.; Yu, L. Q. J. Biobased Mater. Bioenergy 2012, 6, 656.

    CAS  Google Scholar 

  18. Johnson, B. J. J. Turfgrass Manage. 1995, 1(1), 49.

    CAS  Google Scholar 

  19. Grossmann, K.; Kwiatkowski, J. Pestic. Biochem. Physiol. 2000, 66, 83.

    CAS  Google Scholar 

  20. Riar, D. S.; Norsworthy, J. K. Weed Technol. 2011, 25, 548.

    CAS  Google Scholar 

  21. Gao, Y.; Pan, L.; Sun, Y.; Zhang, T.; Dong, L. Y.; Li, J. Pestic. Biochem. Physiol. 2017, 143, 231.

    CAS  PubMed  Google Scholar 

  22. Xu, W. Y.; Di, C.; Zhou, S. X.; Liu, J.; Li, L.; Liu, F. X.; Yang, X. L.; Ling, Y.; Su, Z. Front. Genet. 2015, 6, 306. DOI: https://doi.org/10.3389/fgene.2015.00306.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  23. Deng, X. L.; Zhao, P. Y.; Zhou, X. M.; Bai, L. Y. Chem. Eng. J. 2021, 405, 126979.

    CAS  Google Scholar 

  24. Vogel, C.; Aebi, R. DE Patent 19732328340.

  25. Diyanat, M.; Saeidian, H.; Baziar, S.; Mirjafary, Z. Environ. Sci. Pollut. Res. 2019, 26, 21579.

    CAS  Google Scholar 

  26. Kuk, Y. I.; Jung, H. I.; Kwon, O. D.; Lee, D. J.; Burgos, N. R.; Guh, J. O. Pest Manage. Sci. 2003, 59, 949.

    CAS  Google Scholar 

  27. Kumar, V.; Hooda, V. S.; Nandal, D. P.; Kumar, S.; Gupta, G. J. Appl. Nat. Sci. 2017, 9, 1958.

    CAS  Google Scholar 

  28. Kumar, B.; Sharma, R.; Singh, S. B.; Shukla, L.; Khare, T. R. Indian J. Agric. Sci. 2014, 84, 1018.

    CAS  Google Scholar 

  29. Scarponi, L.; Del Buono, D.; Vischetti, C. Pest Manage. Sci. 2005, 61, 371.

    CAS  Google Scholar 

  30. Scarponi, L.; Vischetti, C; Hassan, N. M. Agrochimica 2002, 46, 165.

    CAS  Google Scholar 

  31. Chen, Y.; Shen, X. F.; Fang, Y. Can. J. Plant Sci. 2013, 93, 237.

    CAS  Google Scholar 

  32. Deng, X. L.; Zheng, W. N.; Zhou, X. M.; Bai, L. Y. Agronomy 2020, 10, 317.

    CAS  Google Scholar 

  33. Deng, X. L.; Zheng, W. N.; Zhan, Q. C.; Deng, Y. N.; Zhou, Y.; Bai, L. Y. Molecules 2020, 25, 4986.

    CAS  PubMed Central  Google Scholar 

  34. Luo, Y.; Zhang, S.; Liu, Z.-J.; Chen, W.; Fu, J.; Zeng, Q. F. Zhu, H.-L. Eur. J. Med. Chem. 2013, 64, 54.

    CAS  PubMed  Google Scholar 

  35. Xu, M.; Zhu, Y.-B.; Wang, M.; Khan, I. A.; Liu, X.-H.; Weng, J.-Q. Lett. Drug Des. Discovery 2018, 15, 347.

    CAS  Google Scholar 

  36. Zheng, W. N.; Zhu, Z. Y.; Deng, Y. N.; Wu, Z. C.; Zhou, Y.; Zhou, X. M.; Bai, L. Y.; Deng, X. L. Crystals 2018, 8, 75.

    Google Scholar 

  37. Sun, J. L.; Zhou, Y. M. Molecules 2015, 20, 5625.

    CAS  PubMed Central  PubMed  Google Scholar 

  38. Sanchez Costa, L.; Pujol Boira, J.; Aragó Iglesias, M.; Rodríguea Martínez, P.; Medina Sala, M. Anal. Methods 2020, 12, 4080.

    CAS  PubMed  Google Scholar 

  39. Zambito Marsala, R.; Capri, E.; Russo, E.; Bisagni, M.; Colla, R.; Lucini, L.; Gallo, A.; Suciu, N. A. Sci. Total Environ. 2020, 736, 139730.

    CAS  PubMed  Google Scholar 

  40. Aghekyan, A. A.; Arakelyan, E. A.; Panosyan, G. A.; Khachatryan, A. G.; Markaryan, E. A. Chem. Heterocycl. Compd. 2009, 45, 1069. [Khim. Geterotsikl. Soedin. 2009, 1338.]

  41. Deng, X. L.; Zhang, L.; Hu, X. P.; Yin, B.; Liang, P.; Yang, X. L. Chin. Chem. Lett. 2016, 27, 251.

    CAS  Google Scholar 

  42. Deng, X. L.; Zhou, X. M.; Wang, Z. Y.; Rui, C. H.; Yang, X. L. Chin. J. Struct. Chem. 2018, 37, 551.

    CAS  Google Scholar 

  43. Hui, J.; Zhong, H. Y.; Zhang, J. Y. Chin. J. Struct. Chem. 2019, 38, 2070.

    CAS  Google Scholar 

  44. Prasath, R.; Sarveswari, S.; Ng, S. W.; Tiekink, E. R. T. Acta Crystallogr., Sect. E: Struct. Rep. Online 2013, 69, o1274.

    Google Scholar 

  45. Meng, X. M.; Wang, S. X.; Li, Y. M.; Zhu, M. Z.; Guo, Q. X. Chem. Commun. 2012, 4196.

  46. Katritzky, A. R.; Huang, T. B.; Voronkov, M. V.; Steel, P. J. J. Org. Chem. 2000, 65, 8069.

    CAS  PubMed  Google Scholar 

  47. Slepukhin, P. А.; Voinkov, E. K.; Ulomskiy, E. N.; Savateev, K. V.; Kopchuk, D. S.; Zyryanov, G. V.; Fedotov, V. V.; Charushin, V. N.; Chupakhin, O. N.; Rusinov, V. L. Chem. Heterocycl. Compd. 2019, 55, 989. [Khim. Geterotsikl. Soedin. 2019, 55, 989.]

  48. Löser, R.; Pitzschler, R.; Köckerling, M. Crystals 2017, 7, 290.

    Google Scholar 

  49. Shen, Z. H.; Shi, Y. X.; Yang, M. Y.; Sun, Z. H.; Weng, J. Q.; Tan, C. X.; Liu, X. H.; Li, B. J.; Zhao, W. G. Chin. J. Struct. Chem. 2016, 35, 457.

    CAS  Google Scholar 

  50. Wang, L.; Lu, C. R.; Yue, Y. N.; Feng, C. Org. Lett. 2019, 21, 3514.

    CAS  PubMed  Google Scholar 

  51. Xu, G. F.; Yang, X. L.; Jiang, B. B.; Lei, P.; Liu, X. L.; Wang, Q. M.; Zhang, X. B.; Ling, Y. Bioorg. Med. Chem. Lett. 2016, 26, 1849.

    CAS  PubMed  Google Scholar 

  52. Deng, X. L.; Xie, J.; Li, Y. Q.; Yuan, D. K.; Hu, X. P.; Zhang, L.; Wang, Q. M.; Chi, M.; Yang, X. L. Chin. Chem. Lett. 2016, 27, 566.

    CAS  Google Scholar 

  53. Wu, Q. L.; Huang, Z. Z.; Bai, P.; Wang, T. T.; Zhao, J. L. CN Patent 105601529.

  54. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.

    CAS  Google Scholar 

  55. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Adv. 2015, A71, 3.

    Google Scholar 

  56. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.

    Google Scholar 

  57. Xie, Y.; Chi, H. W.; Guan, A. Y.; Liu, C. L.; Ma, H. J.; Cui, D. L. Bioorg. Med. Chem. 2016, 24, 428.

    CAS  PubMed  Google Scholar 

  58. Zhang, X. B.; Lei, P.; Sun, T. D.; Jin, X. Y.; Yang, X. L.; Ling, Y. Molecules 2017, 22, 2085.

    PubMed Central  Google Scholar 

  59. Khazhieva, I. S.; Demkin, P. M.; Eltsov, O. S.; Nein, Y. I.; Kalinina, T. A.; Fan, Z. J; Chen, L.; Zhao, B.; Glukhareva, T. V.; Morzherin, Y. Y. Chem. Heterocycl. Compd. 2018, 54, 956. [Khim. Geterotsikl. Soedin. 2018, 54, 956.]

  60. Deng, X. L.; Zheng, W. N.; Jin, C.; Bai, L. Y. ACS Omega 2020, 5, 23996.

    CAS  PubMed Central  PubMed  Google Scholar 

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Correspondence to Lian-Yang Bai.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(1), 49–54

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Deng, XL., Zhu, CH., Zhou, XM. et al. Construction and Characterization of 3,7-Dichloro-N-(2,6-Diethylphenyl)-N-(2-Propoxyethyl)Quinolone-8-Carboxamide: A Potential Novel Pesticide Compound. Chem Heterocycl Comp 57, 49–54 (2021). https://doi.org/10.1007/s10593-021-02866-x

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  • DOI: https://doi.org/10.1007/s10593-021-02866-x

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