Synthesis, characterization and herbicidal activity of new thiazoline derivatives

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Synthesis, characterization and herbicidal activity of new thiazoline derivatives

Jian-Chao Liu , Ying Liang , Hong-Wu He

Citation: Jian-Chao Liu, Ying Liang, Hong-Wu He. Synthesis, characterization and herbicidal activity of new thiazoline derivatives[J]. Chinese Chemical Letters, 2013, 24(3): 233-235. shu

shu

Synthesis, characterization and herbicidal activity of new thiazoline derivatives

通讯作者: Hong-Wu He,

摘要: A series of new thiazoline derivatives 2-alkyl(aryl) imino-4-amino-5-ethoxycarbonyl-3-phenyl-3Hthiazoline (3) and bis(2-imino-4-amino-5-ethoxycarbonyl-3-phenyl-3H-thiazoline alkylene (4) have been synthesized by reactions of intermediate 4-amino-5-ethoxycarbonyl-2-methylthio-3-phenyl-3H-thiazolinium sulphate (2) with alkylamines or arylamine in 64%-89% yields. The structures of 3 and 4 have been confirmed by ¹H NMR, EI-MS, IR spectroscopy and elemental analyses. Some compounds exhibited high or moderate herbicidal activities against the roots of rapeseed and barnyard grass at 100 mg/L.

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English

Synthesis, characterization and herbicidal activity of new thiazoline derivatives

1.
a College of Chemistry, Central China Normal University, Wuhan 430079, China;
2.
b Hubei Biopesticide Engineering Research Center, Hubei Academy of Agricultural Science, Wuhan 430064, China

Corresponding author: Hong-Wu He,

Received Date: 19 November 2012
Available Online: 14 February 2013

Abstract: A series of new thiazoline derivatives 2-alkyl(aryl) imino-4-amino-5-ethoxycarbonyl-3-phenyl-3Hthiazoline (3) and bis(2-imino-4-amino-5-ethoxycarbonyl-3-phenyl-3H-thiazoline alkylene (4) have been synthesized by reactions of intermediate 4-amino-5-ethoxycarbonyl-2-methylthio-3-phenyl-3H-thiazolinium sulphate (2) with alkylamines or arylamine in 64%-89% yields. The structures of 3 and 4 have been confirmed by ¹H NMR, EI-MS, IR spectroscopy and elemental analyses. Some compounds exhibited high or moderate herbicidal activities against the roots of rapeseed and barnyard grass at 100 mg/L.

Key words:

1. [1] A.C. Gaumont, M. Gulea, J. Levillain, Overview of the chemistry of 2-thiazolines, J. Chem. Rev. 109 (2009) 1371-1401.[1] A.C. Gaumont, M. Gulea, J. Levillain, Overview of the chemistry of 2-thiazolines, J. Chem. Rev. 109 (2009) 1371-1401.
2. [2] K. Gholivand, S. Farshadian, M.F. Erben, C.O.D. Vedova, Synthesis and characterization of the first phosphonic diamide containing thiazolyl gtoups: structural properties and tautomeric equilibrium, J. Mol. Struct. 978 (2010) 67-73.[2] K. Gholivand, S. Farshadian, M.F. Erben, C.O.D. Vedova, Synthesis and characterization of the first phosphonic diamide containing thiazolyl gtoups: structural properties and tautomeric equilibrium, J. Mol. Struct. 978 (2010) 67-73.
3. [3] A. Hirashima, A. Rafaeli, C. Gileadi, E. Kuwano, Three-dimensional quantitative structure-activity studies of octopaminergic agonists responsible for the inhibition of sexoheromone production in Hercoverpa armigera, Bioorg. Med. Chem. 7 (1999) 2621-2628.[3] A. Hirashima, A. Rafaeli, C. Gileadi, E. Kuwano, Three-dimensional quantitative structure-activity studies of octopaminergic agonists responsible for the inhibition of sexoheromone production in Hercoverpa armigera, Bioorg. Med. Chem. 7 (1999) 2621-2628.
4. [4] A. Hirashima, M. Morimoto, E. Kuwano, E. Taniguchi, M. Eto, Three-dimensional common-feature hypotheses for octopamine agonist 2-(arylimino)imidazolidines, Bioorg. Med. Chem. 10 (2002) 117-123.[4] A. Hirashima, M. Morimoto, E. Kuwano, E. Taniguchi, M. Eto, Three-dimensional common-feature hypotheses for octopamine agonist 2-(arylimino)imidazolidines, Bioorg. Med. Chem. 10 (2002) 117-123.
5. [5] R. Caujolle, H. Amarouch, M. Payard, et al., Aminothiazine and aminothiazole open analogs of levamisole: synthesis and anthelminthic activity, Eur. J. Med. Chem. 24 (1989) 287-291.[5] R. Caujolle, H. Amarouch, M. Payard, et al., Aminothiazine and aminothiazole open analogs of levamisole: synthesis and anthelminthic activity, Eur. J. Med. Chem. 24 (1989) 287-291.
6. [6] P.E. Bender, D.T. Hill, P.H. Offen, et al., 5,6-Diaryl-2,3-dihydroimidazo[2,1-b]thiazoles: a new class of immunoregulatory antiinflammatory agents, J. Med. Chem. 28 (1985) 1169-1177.[6] P.E. Bender, D.T. Hill, P.H. Offen, et al., 5,6-Diaryl-2,3-dihydroimidazo[2,1-b]thiazoles: a new class of immunoregulatory antiinflammatory agents, J. Med. Chem. 28 (1985) 1169-1177.
7. [7] X.Y. Xu, X.H. Qian, Z. Li, G.H. Song, W.D. Chen, Synthesis and fungicidal activity of fluorine-containing phenylimino-thiazolidines derivatives, J. Fluor. Chem. 125 (2004) 1159-1162.[7] X.Y. Xu, X.H. Qian, Z. Li, G.H. Song, W.D. Chen, Synthesis and fungicidal activity of fluorine-containing phenylimino-thiazolidines derivatives, J. Fluor. Chem. 125 (2004) 1159-1162.
8. [8] C.X. Liu, X.Y. Xu, Z. Li, et al., Synthesis and biological activities of hydroxylprotected fluorine-containing 4,4-dihydroxylmethyl-2-aryl-iminothiazolidines, J. Fluor. Chem. 126 (2005) 53-58.[8] C.X. Liu, X.Y. Xu, Z. Li, et al., Synthesis and biological activities of hydroxylprotected fluorine-containing 4,4-dihydroxylmethyl-2-aryl-iminothiazolidines, J. Fluor. Chem. 126 (2005) 53-58.
9. [9] K. Takasu, K. Pudhom, M. Kaiser, R. Brun, M. Ihara, Synthesis and antimalarial efficacy of aza-fused rhodacyanines in vitro and in the P. berghei mouse model, J. Med. Chem. 49 (2006) 4795-4798.[9] K. Takasu, K. Pudhom, M. Kaiser, R. Brun, M. Ihara, Synthesis and antimalarial efficacy of aza-fused rhodacyanines in vitro and in the P. berghei mouse model, J. Med. Chem. 49 (2006) 4795-4798.
10. [10] R.H. Mizzoni, P.C. Eisman, Some thiazolines and thiazolidinones with antituberculous activity, J. Am. Chem. Soc. 80 (1958) 3471-3475.[10] R.H. Mizzoni, P.C. Eisman, Some thiazolines and thiazolidinones with antituberculous activity, J. Am. Chem. Soc. 80 (1958) 3471-3475.
11. [11] G. Turan-Zitouni, D.M. Sivaci, Z.A. Kaplancikli, A. Ozdemir, Synthesis and antimicrobial activity of some pyridinyliminothiazoline derivatives, Il Farmaco 57 (2002) 569-572.[11] G. Turan-Zitouni, D.M. Sivaci, Z.A. Kaplancikli, A. Ozdemir, Synthesis and antimicrobial activity of some pyridinyliminothiazoline derivatives, Il Farmaco 57 (2002) 569-572.
12. [12] M.W. Ding, S.J. Yang, J. Zhu, New efficient synthesis of 2-substituted 5,6,7,8-tetrahydro-benzo-thieno[2,3-d]pyrimidin-4(3H)-ones, Synthesis 1 (2004) 75-79.[12] M.W. Ding, S.J. Yang, J. Zhu, New efficient synthesis of 2-substituted 5,6,7,8-tetrahydro-benzo-thieno[2,3-d]pyrimidin-4(3H)-ones, Synthesis 1 (2004) 75-79.
13. [13] J.C. Liu, H.W. He, Synthesis, characterization and fungicidal activity of new thienopyridopyrimidine derivatives, Synth. Commun. 42 (2012) 2075-2082.[13] J.C. Liu, H.W. He, Synthesis, characterization and fungicidal activity of new thienopyridopyrimidine derivatives, Synth. Commun. 42 (2012) 2075-2082.
14. [14] B.F. Han, Q.M. Shi, X.F. Wang, et al., Synthesis and bioactivity of novel 3-(1-hydroxyethylidene)-5-substituted-pyrrolidine-2,4-dione derivatives, Chin. Chem. Lett. 23 (2012) 1023-1026.[14] B.F. Han, Q.M. Shi, X.F. Wang, et al., Synthesis and bioactivity of novel 3-(1-hydroxyethylidene)-5-substituted-pyrrolidine-2,4-dione derivatives, Chin. Chem. Lett. 23 (2012) 1023-1026.

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