Discovery of a novel series of phenyl pyrazole inner salts based on fipronil as potential dual-target insecticides

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 16, 2014, Pages 3577-3583

  Jiang, Dingxin ^a   Zheng, Xiaohua ^a   Shao, Guang ^b   Ling, Zhang ^a   Xu, Hanhong ^a  

^a SOUTH CHINA AGRICULTURAL UNIVERSITY   (China)

^b SUN YAT SEN UNIVERSITY   (China)

Author keywords

dual target insecticide; fipronil derivatives; nicotinic acetylcholine receptors; phenyl pyrazole inner salts; aminobutyric acid receptors

Indexed keywords

AMINO ACIDS; BIOACTIVITY; HYDROGEN BONDS; INSECTICIDES;

AMINOBUTYRIC ACIDS; FIPRONIL; INSECTICIDAL ACTIVITY; NICOTINIC ACETYLCHOLINE RECEPTORS; PLUTELLA XYLOSTELLA; PYRAZOLES; QUATERNARY AMMONIUM SALT; STRUCTURE ACTIVITY RELATIONSHIPS; GAMMA-AMINOBUTYRIC ACIDS;

SALTS;

PLUTELLA XYLOSTELLA; PLUTELLIDAE;

FIPRONIL; INSECTICIDE; PYRAZOLE; PYRAZOLE DERIVATIVE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; DRUG EFFECT; MOTH; STRUCTURE ACTIVITY RELATION;

ANIMALS; DRUG DESIGN; INSECTICIDES; MOLECULAR STRUCTURE; MOTHS; PYRAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84899537108     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf405512e     Document Type: Article

References (35)

1. Moffat, A. S. New chemicals seek to outwit insect pests Science 1993, 261, 550-551
2. Ikeda, T.; Zhao, X.; Nagata, K.; Kono, Y.; Shono, T.; Yeh, J. Z. Fipronil modulation of γ-aminobutyric acid (A) receptors in rat dorsal root ganglion neurons J. Pharmacol. Exp. Ther. 2001, 296, 914-921
3. Hainzl, D.; Casida, J. E. Fipronil insecticide: novel photochemical desulfinylation with retention of neurotoxicity Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 12764-12767
4. Li, A.; Yang, Y.; Wu, S.; Li, C.; Wu, Y. Investigation of resistance mechanisms to fipronil in diamondback moth (Lepidoptera Plutellidae) J. Econ. Entomol. 2006, 99, 914-919
5. Kristensen, M.; Hansen, K. K.; Jensen, K. M. Cross-resistance between dieldrin and fipronil in German cockroach (Dictyoptera Blattellidae) J. Econ. Entomol. 2005, 98, 1305-1310
6. Tang, J.; Li, J.; Shao, Y.; Yang, B. J.; Liu, Z. W. Fipronil resistance in the white backed planthopper (Sogatella furcifera): possible resistance mechanisms and cross-resistance Pest Manage. Sci. 2010, 66, 121-125
7. Ozoe, Y.; Yagi, K.; Nakamura, M.; Akamatsu, M.; Miyake, T.; Matsumura, F. Fipronil-related heterocyclic compounds: structure-activity relationships for interaction with γ-aminobutyric acid-and voltage-gated ion channels and insecticidal action Pestic. Biochem. Physiol. 2000, 66, 92-104
8. Zhang, Y. B.; Zhang, Y. New Progress of Pesticide in World (in Chinese); Chemical Industry: Beijing, China, 2006; p 152.
9. Peng, Y. Q.; Gao, C. F.; Ma, C. Y.; Mao, Y. X.; Shen, J. L. Risk assessment and genetic analysis of fipronil resistance and insecticide susceptibility in the small brown planthopper, Laodelphax striatellus (Homoptera: Delphacidae) (in Chinese) Chin. J. Rice Sci. 2009, 23, 645-652
10. Niu, H. T.; Luo, W. C.; Zong, J. P.; Wei, S. J.; Wang, H. Y.; Pan, Z. X. Realized heritability of resistance to butene-fipronil in diamondback moth, Plutella xylostella (in Chinese) Acta Phytophylacica Sinica 2008, 35, 165-168
11. Jiang, D. X.; Lu, X. L.; Hu, S.; Zhang, X. B.; Xu, H. H. A new derivative of fipronil: effect of adding a glycinyl group to the 5-amine of pyrazole on phloem mobility and insecticidal activity Pestic. Biochem. Physiol. 2009, 95, 126-130
12. Zheng, X. H.; Jiang, D. X.; Liu, Z. C.; Xu, H. H. Synthesis, characterization and bioactivity of fipronil derivatives as a lead for new insecticide Indian J. Chem. Technol. 2010, 17, 215-219
13. Xu, H. H.; Jiang, D. X.; Hu, S.; Zhang, X. W.; Liu, Z. C.; Zheng, X. H. Fipronil-GABA conjugate-a phloem mobile insecticide against sucking insect. 4th Pan Pacific Conference on Pesticide Science, Hawaii, USA; American Chemical Society: Washington DC, 2008; p 39.
14. Xu, H. H.; Jiang, D. X.; Hu, S. Synthesis of guided pesticide and their biological activities. 11th IUPAC International Congress of Pesticide Chemistry, Kobe, Japan; Pesticide Science Society of Japan: Tokyo, Japan, 2006; p 26.
15. Guo, Y. S.; Guo, Z. R. Design of multiple targeted drugs (in Chinese) Acta Pharm. Sinica 2009, 44, 276-281
16. Guo, Z. R. Strategy of molecular drug design: dual-target drug design (in Chinese) Acta Pharm. Sinica 2009, 44, 209-218
17. Jones, A. K.; Sattelle, D. B. Diversity of insect nicotinic acetylcholine receptor subunits Adv. Exp. Med. Biol. 2010, 683, 25-43
18. Kizawa, Y.; Takayanagi, I. Nicotinic stimulant, DMPP (1,1-dimethyl-4- phenylpiperazinium iodide) on the isolated bronchial smooth muscle preparation of guinea-pig Gen. Pharmacol. 1984, 15, 149-150
19. 3H] nicotine to a single class of high affinity sites in rat brain membranes Mol. Pharmacol. 1986, 29, 448-454
20. Romanelli, M. N.; Manetti, D.; Scapecchi, S.; Borea, P. A.; Dei, S.; Bartolini, A. Structure-affinity relationships of a unique nicotinic ligand: N (1)-dimethyl- N (4)-phenylpiperazinium iodide (DMPP) J. Med. Chem. 2001, 44, 3946-3955
21. Simsek, R.; Chang, F. J.; Lee, M.; Dukat, M.; Damaj, M. I.; Martin, B. R. Quaternary ammonium 3-(aminoethoxy)pyridines as antinociceptive agents Bioorg. Med. Chem. Lett. 2003, 13, 2917-2920
22. Gündisch, D.; Andrä, M.; Munoz, L.; Tilotta, M. C. Synthesis and evaluation of phenylcarbamate derivatives as ligands for nicotinic acetylcholine receptors Bioorg. Med. Chem. 2004, 12, 4953-4962
23. Toda, N.; Tago, K.; Marumoto, S.; Takami, K.; Ori, M.; Yamada, N. A conformational restriction approach to the development of dual inhibitors of acetylcholinesterase and serotonin transporter as potential agents for Alzheimer's disease Bioorg. Med. Chem. 2003, 11, 4389-4415
24. Kogen, H.; Toda, N.; Tago, K.; Marumoto, S.; Takami, K.; Ori, M. Design and synthesis of dual inhibitors of acetylcholinesterase and serotonin transporter targeting potential agents for Alzheimer's disease Org. Lett. 2002, 4, 3359-3362
25. Cavalli, A.; Bolognesi, M. L.; Minarini, A.; Rosini, M.; Tumiatti, V.; Recanatini, M. Multi-target-directed ligands to combat neurodegenerative diseases J. Med. Chem. 2008, 51, 347-372
26. Meunier, B. Hybrid molecules with a dual mode of action: dream or reality? Acc. Chem. Res. 2008, 41, 69-77
27. Woo, L. W. L.; Bubert, C.; Purohit, A.; Potter, B. V. L. Hybrid dual aromatase-steroid sulfatase inhibitors with exquisite picomolar inhibitory activity ACS Med. Chem. Lett. 2011, 2, 243-247
28. Wenzel, N. I.; Chavain, N.; Wang, Y.; Friebolin, W.; Maes, L.; Pradines, B. Antimalarial versus cytotoxic properties of dual drugs derived from 4-aminoquinolines and Mannich bases: interaction with DNA J. Med. Chem. 2010, 53, 3214-3226
29. Detsi, A.; Bouloumbasi, D.; Prousis, K. C.; Koufaki, M.; Athanasellis, G.; Melagraki, G. Design and synthesis of novel quinolinone-3-aminoamides and their alpha-lipoic acid adducts as antioxidant and anti-inflammatory agents J. Med. Chem. 2007, 50, 2450-2458
30. Liu, L.; Xue, S. J.; Bu, H. F.; Chen, L. Synthesis and biological activities of 2,4-dichlorophenoxyacetyl(thio)urea and S -(+)-3-methyl-2-(4- chlorophenyl) butyramide derivatives Chem. Res. Chinese Univ. 2010, 26, 929-932
31. Lin, S. W.; Sun, Q.; Ge, Z. M.; Wang, X.; Ye, J.; Li, R. T. Synthesis and structure-analgesic activity relationships of a novel series of monospirocyclopiperazinium salts (MSPZ) Bioorg. Med. Chem. Lett. 2011, 21, 940-943
32. Ye, Z. J.; Xia, S.; Shao, X. H.; Cheng, J. G.; Xu, X. Y.; Xu, Z. P. Design, synthesis, crystal structure analysis, and insecticidal evaluation of phenylazoneonicotinoid J. Agric. Food Chem. 2011, 59, 10615-10623
33. Wang, Y. L.; Cheng, J. G.; Qian, X. H.; Li, Z. Actions between neonicotinoids and key residues of insect nAChR based on an ab initio quantum chemistry study: hydrogen bonding and cooperative π-π interaction Bioorg. Med. Chem. 2007, 15, 2624-2630
34. Chen, L.; Durkin, K. A.; Casida, J. E. Structural model for γ-aminobutyric acid receptor noncompetitive antagonist binding: widely diverse structures fit the same site Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 5185-5190
35. Ohno, I.; Tomizawa, M.; Durkin, K. A.; Casida, J. E.; Kagabu, S. Bis-neonicotinoid insecticides: observed and predicted binding interactions with the nicotinic receptor Bioorg. Med. Chem. Lett. 2009, 19, 3449-3452