SYNTHESIS AND BIOLOGICAL TESTING FOR PESTICIDAL ACTIVITY OF 9-ARYL-N-ARYL, ALKYL-SUBSTITUTED 1,2,3,4,5,6,7,8,9,10-DECAHYDROACRIDINE-1,8-DIONE DERIVATIVES
https://doi.org/ 10.21285/2227-2925-2017-7-1-16-20
Abstract
The purpose of this work is the synthesis and pesticidal activity testing of 9-aryl-N-aryl, alkyl-substituted 1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione derivatives which could become the basis of plant protection products. The substances investigated were obtained by three-component heterocyclization of primary amines with aromatic aldehydes and dimedone. The synthesized compounds were tested for certain types of insecticide (against toxoptera graminum, musca domestica, meloidogyne incognita, heliothis virescens, diabrotica undecimpunctata howardi, caenorhabditis elegans), fungicidal (against drechslera, erysiphe, puccinia, peronospora) and herbicidal (against amaranthus retroflexus, brassica rapa, abutilon theophrasti, alopecurus myosuroides , avena fatua, echinochloa crus galli) activities. All synthesized compounds have shown promising insecticidal activities against toxoptera graminum. 9-(4-methoxyphenyl)-, N-2-phenylethyl-substituted, 9-(3,4-methoxyphenyl)-, N-2-carboxyethyl-substituted and 9-(2-hydroxyphenyl)-N-octyl-substituted derivatives have shown significant herbicidal activities against amaranthus retroflexus. 9-phenyl-N-methyl-substituted derivative was active against amaranthus retroflexus, brassica rapa, and abutilon theophrasti. Only this compound showed antifungal activity against drechslera.
About the Author
A. N. Pyrko
International Sakharov Environmental Institute Belarussian State University
Russian Federation
Russian Federation
References
1. Safaei-Ghomi J., Ghasemzadeh M. A., Zahedi S. ZnO nanoparticles: a highly effective and readily recyclable catalyst for the one-pot synthesis of 1, 8-dioxodecahydroacridine and dioxooctahydroxanthene derivatives //Journal of the Mexican Chemical Society. 2013. V. 57, N. 1. P. 1-7.
2. Nakhi A., Srinivas P. T. V., Rahman M. S. Amberlite IR-120H catalyzed MCR: design, synthesis and crystal structure analysis of 1, 8-dioxodecahydroacridines as potential inhibitors of sirtuins //Bioorganic and Medicinal Chemistry Letters. 2013. V. 23, N. 6. P. 1828-1833.
3. Pyrko A.N. Synthesis and Transformations of New 1,2,3,4,5,6,7,8,9,10-Deca-hydroacridine-1,8-dione Derivatives // Russian Journal of Organic Chemistry. 2008. V. 44, N. 8. P. 1215-1224.
4. Kumar A., Sharma S. A grinding-induced catalyst- and solvent-free synthesis of highly functionalized 1,4-dihydropyridines via a domino multicomponent reaction // Green Chem. 2011. Vol. 13. P. 2017-2020.
5. To Q. H., Lee Y. R., Kim S. H. Efficient one-pot synthesis of acridinediones by indium(III) triflate-catalyzed reactions of β-enaminones, aldehydes, and cyclic 1,3-dicarbonyls // Bulletin of the Korean Chemical Society. 2012. Vol. 33, N. 4. P. 1170-1176.
6. Shchekotikhin Yu.M., Nikolaeva T.G., Shub G.M., Kriven’ko A.P.Synthesis and antibacterial activity of substituted 1,8-dioxodecahydroacridines // Khim.-Farm. Zh. 2001. V. 35, N 4. P. 206-211.
7. Gutsulyak Kh. V., Manzhara V. S., Mel’nik M. V., Kalinc T. I. Relationship between the structure and photostability of decahydroacridine derivatives // J. Appl. Spectr. 2005. Vol. 72, No. 4. P. 488-494.
Review
For citations:
Pyrko A.N. SYNTHESIS AND BIOLOGICAL TESTING FOR PESTICIDAL ACTIVITY OF 9-ARYL-N-ARYL, ALKYL-SUBSTITUTED 1,2,3,4,5,6,7,8,9,10-DECAHYDROACRIDINE-1,8-DIONE DERIVATIVES. Proceedings of Universities. Applied Chemistry and Biotechnology. 2017;7(2):16-20. (In Russ.) https://doi.org/ 10.21285/2227-2925-2017-7-1-16-20
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