Citation: Hong Dai, Yan-Shuang Xiao, Zhong Li, Xiao-Yong Xu, Xu-Hong Qian. The thiazoylmethoxy modifi cation on pyrazole oximes：Synthesis and insecticidal biological evaluation beyond acaricidal activity[J]. Chinese Chemical Letters, ;2014, 25(7): 1014-1016. doi: 10.1016/j.cclet.2014.06.011 shu

The thiazoylmethoxy modifi cation on pyrazole oximes：Synthesis and insecticidal biological evaluation beyond acaricidal activity

1.
a Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China;
2.
b College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, China

Corresponding author: Hong Dai,
Received Date: 15 May 2014
Available Online: 30 May 2014
Fund Project: This workwas financial supported by the National Natural Science Foundation of China (No. 21202089) (No. 21202089) China Postdoctoral Science Foundation (No. 2013M531145) (No. 2013M531145)

A series of new pyrazole oximes bearing substituted thiazole ring were designed and prepared. The structures of the title compounds were identified by spectral analyses. The results of primary bioassay indicated that some targeted compounds exhibited promising insecticidal activity besides acaricidal activity, particularly; compounds 8c and 8d were more potent against Tetranychus cinnabarinus and Plutella xylostella than other analogues.
- Pyrazole oxime,
- Substituted thiazole,
- Acaricidal activity,
- Insecticidal activity
1. [1]
  [1] Y. Li, H.Q. Zhang, J. Liu, X.P. Yang, Z.J. Liu, Stereoselective synthesis and antifungal activities of (E)-α-(methoxyimino)benzeneacetate derivatives containing 1,3,5-substituted pyrazole ring, J. Agric. Food Chem. 54 (2006) 3636-3640.
2. [2]
  [2] P.L. Zhao, F. Wang, M.Z. Zhang, et al., Synthesis, fungicidal, and insecticidal activities of β-methoxyacrylate-containing N-acetyl pyrazoline derivatives, J. Agric. Food Chem. 56 (2008) 10767-10773.
3. [3]
  [3] P.L. Zhao, L. Wang, X.L. Zhu, et al., Subnanomolar inhibitor of cytochrome bc₁ complex designed by optimizing interaction with conformationally flexible residues, J. Am. Chem. Soc. 132 (2010) 185-194.
4. [4]
  [4] H.J. Song, Y.X. Liu, L.X. Xiong, et al., Design, synthesis, and insecticidal evaluation of newpyrazole derivatives containing imine, oxime ether, and dihydroisoxazoline groups based on the inhibitor binding pocket of respiratory complex I, J. Agric. Food Chem. 61 (2013) 8730-8736.
5. [5]
  [5] X.M. Zou, M. Liu, H.Z. Yang, et al., Preparation of pyridine oxime ether derivatives as pesticides and acaricides, CN 101659656, 2010.
6. [6]
  [6] G.P. Ouyang, X.J. Cai, Z. Chen, et al., Synthesis and antiviral activities of pyrazole derivatives containing an oxime moiety, J. Agric. Food Chem. 56 (2008) 10160-10167.
7. [7]
  [7] G.P. Ouyang, Z. Chen, X.J. Cai, et al., Synthesis and antiviral activity of novel pyrazole derivatives containing oxime esters group, Bioorg. Med. Chem. 16 (2008) 9699-9707.
8. [8]
  [8] L.S. Bai, Y. Wang, X.H. Liu, H.L. Zhu, B.A. Song, Novel dihydropyrazole derivatives linked with multi(hetero)aromatic ring: synthesis and antibacterial activity, Chin. Chem. Lett. 20 (2009) 427-430.
9. [9]
  [9] R.R. Ranatunge, M. Augustyniak, U.K. Bandarage, et al., Synthesis and selective cyclooxygenase-2 inhibitory activity of a series of novel, nitric oxide donorcontaining pyrazoles, J. Med. Chem. 47 (2004) 2180-2193.
10. [10]
  [10] K. Motoba, H. Nishizawa, T. Suzuki, et al., Species-specific detoxification metabolism of fenpyroximate, a potent acaricide, Pestic. Biochem. Physiol. 67 (2000) 73-84.
11. [11]
  [11] P. Maienfisch, H. Huerlimann, A. Rindlisbacher, et al., The discovery of thiamethoxam: a second-generation neonicotinoid, Pest Manag. Sci. 57 (2001) 165-176.
12. [12]
  [12] H. Uneme, K. Iwanaga, N. Higuchi, et al., Synthesis and insecticidal activity of nitroguanidine derivatives, Pestic. Sci. 55 (1999) 202-205.
13. [13]
  [13] D.Y. Hu, B.A. Song, W. He, Progresses in the synthesis and biological activity of thiazole derivatives, Chin. J. Synth. Chem. 14 (2006) 319-328.
14. [14]
  [14] X. Qin, H.B. Yu, H. Dai, et al., Synthesis and plant-growth regulatory activities of novel imine derivatives containing 1H-1,2,4-triazole and thiazole rings, Chin. Chem. Lett. 21 (2010) 283-286.
15. [15]
  [15] L.L. Jiang, Y. Tan, X.L. Zhu, et al., Design, synthesis, and 3D-QSAR analysis of novel 1,3,4-oxadiazol-2(3H)-ones as protoporphyrinogen oxidase inhibitors, J. Agric. Food Chem. 58 (2010) 2643-2651.
16. [16]
  [16] H.M. Refat, A.A. Fadda, Synthesis and antimicrobial activity of some novel hydrazide, benzochromenone, dihydropyridine, pyrrole, thiazole and thiophene derivatives, Eur. J. Med. Chem. 70 (2013) 419-426.
17. [17]
  [17] A. Zablotskaya, I. Segal, A. Geronikaki, et al., Synthesis, physicochemical characterization, cytotoxicity, antimicrobial, anti-inflammatory and psychotropic activity of new N-[1,3-(benzo)thiazol-2-yl]-w-[3,4-dihydroisoquinolin-2(1H)-yl]alkanamides, Eur. J. Med. Chem. 70 (2013) 846-856.
18. [18]
  [18] T.T. Wang, G.F. Bing, X. Zhang, et al., Synthesis and herbicidal activities of 2-cyano-3-benzylaminoacrylates containing thiazole moiety, Bioorg. Med. Chem. Lett. 20 (2010) 3348-3351.
19. [19]
  [19] H.J. Park, K. Lee, S.J. Park, et al., Identification of antitumor activity of pyrazole oxime ethers, Bioorg. Med. Chem. Lett. 15 (2005) 3307-3312.
20. [20]
  [20] T. Hideo, H. Hiroshi, N. Akira, et al., Pyrazole derivative and production thereof, Japan Patent 62053970, 1987.
21. [21]
  [21] Y. Zhao, C.H. Mao, Y.Q. Li, et al., Synthesis, crystal structure, and insecticidal activity of novel N-alkyloxyoxalyl derivatives of 2-arylpyrrole, J. Agric. Food Chem. 56 (2008) 7326-7332.
22. [22]
  [22] Q.Q. Zhao, Y.Q. Li, L.X. Xiong, et al., Design, synthesis and insecticidal activity of novel phenylpyrazoles containing a 2,2,2-trichloro-1-alkoxyethyl moiety, J. Agric. Food Chem. 58 (2010) 4992-4998.
23. [23]
  [23] A.H. Sayyed, J. Ferre, D.J. Wright, Mode of inheritance and stability of resistance to Bacillus thuringiensis var kurstaki in a diamondback moth (Plutella xylostella) population from Malaysia, Pest Manag. Sci. 56 (2000) 743-748.
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