Home Synthesis and insecticidal activity of 6,8-dichloro-quinazoline derivatives containing a sulfide substructure
Article
Licensed
Unlicensed Requires Authentication

Synthesis and insecticidal activity of 6,8-dichloro-quinazoline derivatives containing a sulfide substructure

  • Jian Wu EMAIL logo , Song Bai , Min Yue , Li-Jun Luo , Qin-Cai Shi , Juan Ma , Xian-Li Du , Sheng-Hong Kang , Deyu Hu and Song Yang
Published/Copyright: March 12, 2014
Become an author with De Gruyter Brill

Abstract

A series of 6,8-dichloro-quinazoline derivatives bearing a sulfide group was synthesized and characterized via 1H NMR, 13C NMR, IR and elemental analyses. All the compounds were tested for their insecticidal activity against Plutella xylostella in vitro. The results indicate that the synthesized compounds possess good insecticidal activity. Among these compounds, Vc, Vi, Vj, Vk and Vm displayed 75 %, 85 %, 80 %, 70 % and 63 % activities, respectively. These may prove useful as insecticidal agents.

[1] Alexandre, F. R., Berecibar, A., Wrigglesworth, R., & Besson, T. (2003). Novel series of 8H-quinazolino [4,3-b]quinazolin-8-ones via two Niementowski condensations. Tetrahedron, 59, 1413–1419. DOI: 10.1016/s0040-4020(03)00053-x. http://dx.doi.org/10.1016/S0040-4020(03)00053-X10.1016/S0040-4020(03)00053-XSearch in Google Scholar

[2] An, R., Xiong, Q. Z., Gao, Y. L., Han, F. F., & Bao, X. P. (2011). Synthesis and fungicidal activities of novel dihydrazonylquinazoline derivatives. Chinese Journal of Synthetic Chemistry, 6, 699–704. DOI: 10.3969/j.issn.1005-1511.2011.06.003. (in Chinese) Search in Google Scholar

[3] Asare-Bediako, E., Addo-Quaye, A. A., & Mohammed, A. (2010). Control of diamondback moth (Plutella xylostella) on cabbage (Brassica oleracea var capitata) using intercropping with non-host crops. American Journal of Food Technology, 5, 269–274. DOI: 10.3923/ajft.2010.269.274. http://dx.doi.org/10.3923/ajft.2010.269.27410.3923/ajft.2010.269.274Search in Google Scholar

[4] Brewster, W., Klittich, C., Yao, C. L., & Zhu, Y. M. (2010). W.O. Patent No. 2,010,025,451. Geneva, Switzerland: World Intellectual Property Organization. Search in Google Scholar

[5] Coghlan, M. J., Dreikorn, B. A., Jourdan, G. P., & Suhr, R. G. (1994). U.S. Patent No. 5,296,484. Washington, DC, USA: U.S. Patent and Trademark Office. Search in Google Scholar

[6] Ding, M. W., Liu, D. L., & Li, W. J. (2011). C.N. Patent No. 201,110,306,387. Beijing, China: State Intellectual Property Office of People’s Republic of China. Search in Google Scholar

[7] El-Bayouki, K. A. H. M., Basyouni, W. M., Mohamed, Y. A. F., Aly, M. M., & Abbas, S. Y. (2011). Novel 4(3H)-quinazolinones containing biologically active thiazole, pyridinone and chromene of expected antitumor and antifungal activities. European Journal of Chemistry, 2, 455–462. DOI: 10.5155/eurjchem.2.4.455-462.171. http://dx.doi.org/10.5155/eurjchem.2.4.455-462.17110.5155/eurjchem.2.4.455-462.171Search in Google Scholar

[8] Feng, Q., Liu, Z. L., Xiong, L. X., Wang, M. Z., Li, Y. Q., & Li, Z. M. (2010). Synthesis and insecticidal activities of novel anthranilic diamides containing modified N-pyridylpyrazoles. Journal of Agricultural and Food Chemistry, 58, 12327–12336. DOI: 10.1021/jf102842r. http://dx.doi.org/10.1021/jf102842r10.1021/jf102842rSearch in Google Scholar

[9] Ghorab, M. M., Abdel-Hamide, S. G., Ali, G. M., & Shaurub, E. H. (1996). Synthesis and insecticidal activity of some new 3-[4(3H)-quinazolinone-2-(yl)thiomethyl]-1,2,4-triazole-5-thiols. Pesticide Science, 48, 31–35. DOI: 10.1002/(sici)1096-9063(199609)48:1〈31::aid-ps430〉3.0.co;2-#. http://dx.doi.org/10.1002/(SICI)1096-9063(199609)48:1<31::AID-PS430>3.0.CO;2-#Search in Google Scholar

[10] Hasanshahi, G., Abbasipour, H., Askarianzadeh, A., Karimi, J., & Jahan, F. (2013). Seasonal population fluctuations of the diamondback moth, Plutella xylostella (L.) (Lep.: Plutellidae) on different cauliflower cultivars. Archives Of Phytopathology And Plant Protection, 46, 1136–1149. DOI: 10.1080/03235408.2012.760897. http://dx.doi.org/10.1080/03235408.2012.76089710.1080/03235408.2012.760897Search in Google Scholar

[11] Henrie, R. N., II, Peake, C. J., Cullen, T. G., Lew, A. C., Chaguturu, M. K., & Ray, P. S. (1994). W.O. Patent No. 9,418,980. Geneva, Switzerland: World Intellectual Property Organization. Search in Google Scholar

[12] Hou, S. X., Zhang, S. C., Huang, W. Z., Tang, B. Z., & Liang, P. (2010). Circadian rhythm in susceptibility of Plutella xylostella to chlorpyrifos and its possible mechanisms. Chinese Journal of Pesticide Science, 2010, 229–232. DOI: 10.3969/j.issn.1008-7303.2010.02.20. (in Chinese) Search in Google Scholar

[13] Itsuki, Y., Shibata, M., Kajiki, R., Fukumoto, S., Furuse, K., Yamaji, K., Itou, Y., & Takahashi, S. (2005). W.O. Patent No. 2,005,060,750. Geneva, Switzerland: World Intellectual Property Organization. Search in Google Scholar

[14] Jeschke, P. (2010). The unique role of halogen substituents in the design of modern agrochemicals. Pest Management Science, 66, 10–27. DOI: 10.1002/ps.1829. http://dx.doi.org/10.1002/ps.182910.1002/ps.1829Search in Google Scholar

[15] Jersak, U., & Scheuermann, H. (1978). D.E. Patent No. 2,721,133. Berlin, Germany: The German Patent and Trade Mark Office. Search in Google Scholar

[16] Jin, L. H., He, J., He, M., Xu, W. M., & Yang, S. (2011). The preliminary study of inhibitory mechanism of sulfone compounds xa202 and xt208 against Gibberella zeae. African Journal of Microbiology Research, 5, 4889–4895. DOI: 10.5897/ajmr11.862. 10.5897/AJMR11.862Search in Google Scholar

[17] Kodama, H., Sanpei, O., Abe, N., & Uehara, M. (2005). W.O. Patent No. 2,005,123,695. Geneva, Switzerland: World Intellectual Property Organization. Search in Google Scholar

[18] Li, B., & Xu, J. D. (2002). C.N. Patent No. 1,355,164. Beijing, China: State Intellectual Property Office of People’s Republic of China. Search in Google Scholar

[19] Liu, F., & Huang, Y. J. (2011). Antifungal bioactivity of 6-bromo-4-ethoxyethylthio quinazoline. Pesticide Biochemistry and Physiology, 101, 248–255. DOI: 10.1016/j.pestbp.2011.10.002. http://dx.doi.org/10.1016/j.pestbp.2011.10.00210.1016/j.pestbp.2011.10.002Search in Google Scholar

[20] Rádl, S., Hezky, P., Proška, J., & Krejcí, I. (2000). Synthesis and analgesic activity of some quinazoline analogs of anpirtoline. Archiv der Pharmazie, 333, 381–386. DOI: 10.1002/1521-4184(200011)333:11〈381::aid-ardp381〉3.0.co;2-a. http://dx.doi.org/10.1002/1521-4184(200011)333:11<381::AID-ARDP381>3.0.CO;2-A10.1002/1521-4184(200011)333:11<381::AID-ARDP381>3.0.CO;2-ASearch in Google Scholar

[21] Rosenfeld, D. D., & Gorbaty, M. L. (1972). U.S. Patent No. 3,681,352. Washington, DC, USA: U.S. Patent and Trademark Office. Search in Google Scholar

[22] Sanpei, O., Uehara, M., Niino, N., Kodama, H., & Sakata, K. (2004). W.O. Patent No. 2,004,099,184. Geneva, Switzerland: World Intellectual Property Organization. Search in Google Scholar

[23] Sen, A. B., & Singh, P. R. (1959). Search for new antimalarials. III. Synthesis of some substituted quinazolines. Journal of the Indian Chemical Society, 36, 787–791. Search in Google Scholar

[24] Shang, J., Sun, R. F., Li, Y. Q., Huang, R. Q., Bi, F. C., & Wang, Q. M. (2010). Synthesis and insecticidal evaluation of N-tert-butyl-N′-thio[1-(6-chloro-3-pyridylmethyl)-2-nitroiminoimidazolidine]-N,N′-diacylhydrazines. Journal of Agricultural and Food Chemistry, 58, 1834–1837. DOI: 10.1021/jf903642s. http://dx.doi.org/10.1021/jf903642s10.1021/jf903642sSearch in Google Scholar

[25] Sörgel, S., Paulini, R., Gross, S., Beyer, C., Pohlman, M., Bastiaans, H. M. M., Rack, M., Culbertson, D. L., Anspaugh, D. D., & Thompson, S. (2011). W.O. Patent No. 2,011,061,110. Geneva, Switzerland: World Intellectual Property Organization. Search in Google Scholar

[26] Talekar, N. S., & Shelton, A. M. (1993). Biology, ecology and management of the diamondback moth. Annual Review of Entomology, 38, 275–301. DOI: 10.1146/annurev.en.38.010193.001423. http://dx.doi.org/10.1146/annurev.en.38.010193.00142310.1146/annurev.en.38.010193.001423Search in Google Scholar

[27] Uehara, M., Watanabe, M., Kimura, M., Morimoto, M., & Yoshida, M. (2001). E.P. Patent No. 1,097,932. Munich, Germany: European Patent Office. Search in Google Scholar

[28] Wright, I. G. (1990). E.P. Patent No. 380,264. Munich, Germany: European Patent Office. Search in Google Scholar

[29] Wu, J., Song, B. A., Hu, D. Y., Yue, M., & Yang, S. (2012). Design, synthesis and insecticidal activities of novel pyrazole amides containing hydrazone substructures. Pest Management Science, 68, 801–810. DOI: 10.1002/ps.2329. http://dx.doi.org/10.1002/ps.232910.1002/ps.2329Search in Google Scholar PubMed

[30] Xu, Z. P., & Shao, X. S. (2010). Halogen substituent in modern pesticide design (I). World Pesticides, 32, 7–12. DOI: 10.3969/j.issn.1009-6485.2010.06.002. (in Chinese) Search in Google Scholar

[31] Xu, Z. P., & Shao, X. S. (2011). Halogen substituent in modern pesticide design (II). World Pesticides, 33, 12–19. DOI: 10.3969/j.issn.1009-6485.2011.01.003. (in Chinese) Search in Google Scholar

[32] Xu, W. M., Yang, S., Bhadury, P., He, J., He, M., Gao, L. L., Hu, D. Y., & Song, B. A., (2011). Synthesis and bioactivity of novel sulfone derivatives containing 2,4-dichlorophenyl substituted 1,3,4-oxadiazole/thiadiazole moiety as chitinase inhibitors. Pesticide Biochemistry and Physiology, 101, 6–15. DOI: 10.1016/j.pestbp.2011.05.006. http://dx.doi.org/10.1016/j.pestbp.2011.05.00610.1016/j.pestbp.2011.05.006Search in Google Scholar

[33] Xu, W. M., Han, F. F., He, M., Hu, D. Y., He, J., Yang, S., & Song, B. A. (2012). Inhibition of tobacco bacterial wilt with sulfone derivatives containing an 1,3,4-oxadiazole moiety. Journal of Agricultural and Food Chemistry, 60, 1036–1041. DOI: 10.1021/jf203772d. http://dx.doi.org/10.1021/jf203772d10.1021/jf203772dSearch in Google Scholar PubMed

[34] Yang, S., Zhang, Y., Xiang, H. M., Wang, P. Y., Xue, W., Hu, D. Y., Zhang, Q. Y., & Jin, L. H. (2013). C.N. Patent No. 102,875,481. Beijing, Cjina: State Intellectual Property Office of People’s Republic of China. Search in Google Scholar

[35] Zhang, Y. B. (2006a). Pesticide discovery methods — a review. Agrochemicals, 45, 364–467. DOI: 10.3969/j.issn.1006-0413.2006.06.002. (in Chinese) Search in Google Scholar

[36] Zhang, P. Q. (2006b). Synthesis and bioactivity of halogensubstituted quinazoline (quinazolinone) derivatives. M.S. thesis. Guiyang, China: Guizhou University. Search in Google Scholar

[37] Zhao, Q. Q., Li, Y. Q., Xiong, L. X., & Wang, Q. M. (2010). Design, synthesis and insecticidal activity of novel phenylpyrazoles containing a 2,2,2-trichloro-1-alkoxyethyl moiety. Journal of Agricultural and Food Chemistry, 58, 4992–4998. DOI: 10.1021/jf1001793. http://dx.doi.org/10.1021/jf100179310.1021/jf1001793Search in Google Scholar PubMed

Published Online: 2014-3-12
Published in Print: 2014-7-1

© 2014 Institute of Chemistry, Slovak Academy of Sciences

Articles in the same Issue

  1. Kinetic analysis of cellulose pyrolysis: a short review
  2. Simultaneous determination of ciprofloxacin hydrochloride and hydrocortisone in ear drops by high performance liquid chromatography
  3. Inhibition effect of free ammonia and free nitrous acid on nitrite-oxidising bacteria during sludge liquor treatment: influence of feeding strategy
  4. Thermo-chemical properties of biomass from Posidonia oceanica
  5. Al(III) and Cu(II) simultaneous foam separation: Physicochemical problems
  6. Scale-adaptive simulation of liquid mixing in an agitated vessel equipped with eccentric HE 3 impeller
  7. Alkaline hydrogen peroxide pretreatment of energy crops for biogas production
  8. Synthesis, crystal structures, spectral, electrochemical and magnetic properties of di-µ-phenoxido-bridged dinuclear copper(II) complexes with N-salicylidene-2-hydroxybenzylamine derivatives: axial coordination effect of dimethyl sulphoxide molecule
  9. Hemilabile imino-phosphine palladium(II) complexes: synthesis, molecular structure, and evaluation in Heck reactions
  10. Structure and vibrational spectra of copper(II) 2-pyridylmethanolate tetrahydrate
  11. Synthesis and characterization of a silylated Brazilian clay mineral surface
  12. Nano-titanium oxide doped with gold, silver, and palladium — synthesis and structural characterization
  13. Synthesis and insecticidal activity of 6,8-dichloro-quinazoline derivatives containing a sulfide substructure
  14. Effect of extraction method on phenolic content and antioxidant activity of mistletoe extracts from Viscum album subsp. abietis
  15. Synthesis of melamine-formaldehyde resin functionalised with sulphonic groups and its catalytic activities
  16. Synthesis, characterization, and application of a new tripodal ligand for the preparation of LSCF(6482) perovskite
Downloaded on 26.11.2025 from https://www.degruyterbrill.com/document/doi/10.2478/s11696-014-0540-z/pdf
Scroll to top button