Abstract
In search of new bioactive compounds, a series of maleated rosin-based dithiourea compounds were designed and synthesised with rosin as starting material. All the title compounds were characterised by Fourier transform infra-red spectroscopy (FT-IR), proton nuclear magnetic resonance spectroscopy (1H NMR), and 13C nuclear magnetic resonance spectroscopy (13C NMR). The preliminary bioassay showed that the target compounds exhibited a certain fungicidal activity against Physalospora piricola at a concentration of 50 μg ml-1 and a certain growth herbicidal activity against the root of rape (Brassica campestris L.) at a concentration of 100 μg ml-1.
Acknowledgments
We thank the National Natural Science Foundation of China (No.31060100), the National Natural Science Foundation of Guangxi, China (No.2010GXNSFD013013), the National Natural Science Foundation of Guangxi, China (No.2010GXNSFA013040), Special Fund for Bagui Scholar: Innovation of Key Technology for Pine Resource Cultivation and Industrialization, for financial support. We also thank the Research Institute of Elemento-organic Chemistry, Nankai University, China for the bioassay test.
Conflict of interest statement: The authors declare no conflict of interest.
References
Atta, A.M., EI-Saeed, S.M., Farag, R.K. (2006) New vinylester resins based on rosin for coating applications. React. Funct. Polym. 66:1596–1608.Search in Google Scholar
Cheng Z. Production Technology of Natural Resins. 2nd ed. China Forestry Press, Beijing, 1996.Search in Google Scholar
Chien, S.-C., Xiao, J.-H., Tseng, Y.-H., Kuo, Y.-H., Wang, S.-Y. (2013) Composition and antifungal activity of balsam from Liquidambar formosana Hance. Holzforschung 67:345–351.10.1515/hf-2012-0086Search in Google Scholar
Duan, W.-G., Li, X.-R., Mo, Q.-J., Huang, J.-X., Cen, B., Xu, X.-T., Lei, F.-H. (2011) Synthesis and herbicidal activity of 5-dehydroabietyl-1,3,4-oxadiazole derivatives. Holzforschung 65:191–197.10.1515/hf.2011.016Search in Google Scholar
Fernández, M.A., Tornos, M.P., García, M.D., De Las Heras, B., Villar, A.M., Sáenz M.T. (2001) Anti-inflammatory activity of abietic acid, a diterpene isolated from Pimenta racemosa var. grissea. J. Pharm. Pharmacol 53:867–872.Search in Google Scholar
Ke, S.Y., Xue, S.J. (2006) Synthesis and herbicidal activity of N-(o-fluorophenoxyacetyl) theioureas derivatives and related fused heterocylic compounds. ARKIVOC 10:63–68.10.3998/ark.5550190.0007.a08Search in Google Scholar
Lee, J.S., Hong, S. (2002) Synthesis of acrylic rosin derivatives and application as negative photoresist. Eur. Polym. J. 38:387–392.Search in Google Scholar
Limban, C., Marutescu, L., Chifiriuc, M.C. (2011) Synthesis, spectroscopic properties antipathogenic avtivity of new thiourea derivatives. Molecules 16:7593–7607.10.3390/molecules16097593Search in Google Scholar PubMed PubMed Central
Lin, G.-S., Ma, C.-H., Duan, W.-G., Cen, B., Lei, F.-H., Yang, Z.-Q. (2013) Synthesis and biological activities of α-pinene-based dithiadiazoles. Holzforschung, 67, online since 31.05.2013,1–9.Search in Google Scholar
Mishra, A., Srivastava, K., Tripathi, R., Puri, S.K., Batra, S. (2009) Search for new pharmacophores for antimalarial activity (part III): synthesis and bioevaluation of new 6-thioureido-4-anilinoquinazolines. Eur. J. Med. Chem. 44:4404–4412.Search in Google Scholar
Patel R.B., Chikhalia, K.H., Pannecouque, C., Clercq, E. (2007) Synthesis of novel PETT analogues: 3,4-dimethethoxy phenyl ethyl 1,3,5-triazinyl thiourea derivatives and their antibacterial and anti-HIV studies. J. Braz. Chem. Soc. 18:312–321.10.1590/S0103-50532007000200011Search in Google Scholar
Saeed, S., Rashid, N., Jones, P.G., Ali, M., Hussain, R. (2010) Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and acticancer agents. Eur. J. Med. Chem. 45:1323–1331.Search in Google Scholar
Schultz, T.P., Nicholas, D.D., Ingram, L.L. (2007) Laboratory and outdoor water repellency and dimensional stability of southern pine sapwood treated with a waterborne water repellent made from resin acids. Holzforschung 61:317–322.10.1515/HF.2007.044Search in Google Scholar
Sun, C., Huang, H., Feng, M.Q., Shi, X.L., Zhang, X. D., Zhou, P. (2006) A novel class of potent infuenza virus inhibitors: polysubstituted acylthiourea and its fused heterocycle derivatives. Bioorg. Med. Chem. Lett. 16:162–166.Search in Google Scholar
Talevi, A., Cravero, M.S., Castro, E.A., Bruno-Blanch L.E. (2007) Discovery of anticonvulsant activity of abietic acid through application of linear discriminant analysis. Bioorg. Med. Chem. Lett. 17:1684–1690.Search in Google Scholar
Wiyono, B., Tachibana, S., Tinambunan, D. (2007) Reaction of abietic acid with maleic anhydride and fumaric acid and attempts to find the fundamental component of fortified rosin. Pak. J. Biol. Sci. 10:1588–1595.Search in Google Scholar
Xu, X.T., Leng, F., Duan, W.G., Cen, B., Dong, S.Q., Wang, W.K. (2012a) Synthesis and fungicidal activity of maleated rosin acid acylhydrazone compounds. Chin. J. Pestic. Sci. 14: 253–259.Search in Google Scholar
Xu, X.T., Leng, F., Duan, W.G., Lin, G.S., Mo, Q.J., Wang, W.K. (2012b) Synthesis and herbicidal activity of maleated rosin acid-based amide compounds. Chemistry Bulletin 75:463–468.Search in Google Scholar
Xu, X.T., Ma, X.L., Duan, W.G., Chen, L., Cen, B., Mo, Q.J., Wang, J.Y. (2013) Synthesis and fungicidal activity of dehydroabietyl-1,2,4-triazolo-thiazolidinones. Holzforschung 67:107–112.10.1515/hf-2012-0026Search in Google Scholar
Yadav, J.S., Baishya, G., Dash, U. (2007) Synthesis of (+)-amberketal and its analog from L-abietic acid. Tetrahedron 63:9896–9902.10.1016/j.tet.2007.06.063Search in Google Scholar
©2014 by Walter de Gruyter Berlin/Boston
Articles in the same Issue
- Frontmatter
- Review Article
- Multistage oxygen delignification of high-kappa pine kraft pulp with peroxymonosulfuric acid (Px)
- Original Articles
- Pyrolysis gas-chromatography mass-spectrometry (Py-GC/MS) to identify compression wood in Pinus radiata saplings
- Cationization of Eucalyptus grandis 4-O-methyl glucuronoxylan for application as a wet-end additive in a papermaking process
- Extractives of mechanically wounded wood and knots in beech
- Complex between lignin and a Ti-based coupling agent
- Synthesis and biological activities of maleated rosin-based dithiourea compounds
- Thermoplastic deformation of poplar wood plasticized by ionic liquids measured by a nonisothermal compression technique
- Anomalous thermal expansion behaviors of wood under dry and low-temperature conditions
- Interfacial properties of magnesium phosphate ceramics and sugar maple (Acer saccharum)
- Off-axis tensile strength and evaluation of the in-plane shear strength of paper
- Migration of cesium chloride dissolved in the liquid water of sugi (Cryptomeria japonica D. Don) during drying at 65°C
- Numerical modeling of timber with knots: the progressively damaged lattice approach vs. the equivalent damaged continuum
- Meetings
- Meetings
Articles in the same Issue
- Frontmatter
- Review Article
- Multistage oxygen delignification of high-kappa pine kraft pulp with peroxymonosulfuric acid (Px)
- Original Articles
- Pyrolysis gas-chromatography mass-spectrometry (Py-GC/MS) to identify compression wood in Pinus radiata saplings
- Cationization of Eucalyptus grandis 4-O-methyl glucuronoxylan for application as a wet-end additive in a papermaking process
- Extractives of mechanically wounded wood and knots in beech
- Complex between lignin and a Ti-based coupling agent
- Synthesis and biological activities of maleated rosin-based dithiourea compounds
- Thermoplastic deformation of poplar wood plasticized by ionic liquids measured by a nonisothermal compression technique
- Anomalous thermal expansion behaviors of wood under dry and low-temperature conditions
- Interfacial properties of magnesium phosphate ceramics and sugar maple (Acer saccharum)
- Off-axis tensile strength and evaluation of the in-plane shear strength of paper
- Migration of cesium chloride dissolved in the liquid water of sugi (Cryptomeria japonica D. Don) during drying at 65°C
- Numerical modeling of timber with knots: the progressively damaged lattice approach vs. the equivalent damaged continuum
- Meetings
- Meetings