Fipronil-related heterocyclic compounds: Structure-activity relationships for interaction with γ-aminobutyric acid- and voltage-gated ion channels and insecticidal action

Pesticide Biochemistry and Physiology

Volumn 66, Issue 2, 2000, Pages 92-104

  Ozoe, Yoshihisa ^a   Yagi, Kazuo ^b   Nakamura, Masafumi ^b   Akamatsu, Miki ^c   Miyake, Takashi ^d   Matsumura, Fumio ^d  

^a SHIMANE UNIVERSITY   (Japan)

^b NISSAN CHEMICAL INDUSTRIES LTD   (Japan)

^c KYOTO UNIVERSITY   (Japan)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BLATTARIA; BLATTELLA GERMANICA; INSECTA; MAMMALIA; MUSCA DOMESTICA; PERIPLANETA AMERICANA; TRITIUM;

EID: 0034096149     PISSN: 00483575     EISSN: None     Source Type: Journal    
DOI: 10.1006/pest.1999.2452     Document Type: Article

References (44)

1. J. M. Clark Ed., "Molecular Action of Insecticides on Ion Channels," p. 356, Am. Chem. Soc. Washington, DC, 1995.
2. Bloomquist J. R. Ion channels as targets for insecticides. Annu. Rev. Entomol. 41:1996;163.
3. Soderlund D. M., Bloomquist J. R. Neurotoxic actions of pyrethroid insecticides. Annu. Rev. Entomol. 34:1989;77.
4. Wafford K. A., Sattelle D. B., Gant D. B., Eldefrawi A. T., Eldefrawi M. E. Noncompetitive inhibition of GABA receptors in insect and vertebrate CNS by endrin and lindane. Pestic. Biochem. Physiol. 33:1989;213.
5. Lees G., Calder J. Interaction of lindane isomers with chloride currents in insect membranes: Steric requirements for channel modulation and block. Pestic. Biochem. Physiol. 55:1996;40.
6. Bai D., Lummis S. C. R., Leicht W., Breer H., Sattelle D. B. Actions of imidacloprid and a related nitromethylene on cholinergic receptors of an identified insect motor neurone. Pestic. Sci. 33:1991;197.
7. Zwart R., Oortgiesen M., Vijverberg H. P. M. The nitromethylene heterocycle 1-(pyridin-3-yl-methyl)-2-nitromethylene-imidazolidine distinguishes mammalian from insect nicotinic receptor subtypes. Eur. J. Pharmacol. Environ. Toxicol. Pharmacol. 228:1992;165.
8. F. Colliot, K. A. Kukorowski, D. W. Hawkins, and D. Roberts, "Fipronil, a New Soil and Foliar Broad Spectrum Insecticide," Brighton Crop Protection Conference - Pests and Diseases, pp. 29-34, 1992.
9. Cole L. M., Nicholson R. A., Casida J. E. Action of phenylpyrazole insecticides at the GABA-gated chloride channel. Pestic. Biochem. Physiol. 46:1993;47.
10. Buckingham S. D., Hosie A. M., Roush R. L., Sattelle D. B. Actions of agonists and convulsant antagonists on a Drosophila melanogaster GABA receptor (Rdl) homo-oligomer expressed in Xenopus oocytes. Neurosci. Lett. 181:1994;137.
11. A. M. Hosie, H. A. Baylis, S. D. Buckingham, and, D. B. Sattelle, Actions of the insecticide fipronil, on dieldrin-sensitive and -resistant GABA receptors of Drosophila melanogaster, Br. J. Pharmacol. 115, 909, (, 1995, ).
12. Bloomquist J. R. Cyclodiene resistance at the insect GABA receptor/chloride channel complex confers broad cross resistance to convulsants and experimental phenylpyrazole insecticides. Arch. Insect Biochem. Physiol. 26:1994;69.
13. - channel in insects as target for insecticidal action: A physiological study. Duce I. R. Neurotox '91 - Molecular Basis of Drug and Pesticide Action. 1992;79-104 Elsevier Applied Science.
14. Bascal Z., Holden-Dye L., Willis R. J., Smith S. W. G., Walker R. J. Novel azole derivatives are antagonists at the inhibitory GABA receptor on the somatic muscle cells of the parasitic nematode Ascaris suum. Parasitology. 112:1996;253.
15. Pullman D. A., Smith I. H., Larkin J. P., Casida J. E. Heterocyclic insecticides acting at the GABA-gated chloride channel: 5-Alkyl-2-arylpyrimidines and -1,3-thiazines. Pestic. Sci. 46:1996;237.
16. Whittle A. J. 3-Aryl pyrimidinones: A novel class of potent insecticides. Briggs G. G. Advances in the Chemistry of Insect Control III. 1994;156-170 The Royal Society of Chemistry.
17. Whittle A. J., Fitzjohn S., Mullier G., Pearson D. P. J., Perrior T. R., Taylor R., Salmon R. The use of computer-generated electrostatic surface maps for the design of new 'GABA-ergic' insecticides. Pestic. Sci. 44:1995;29.
18. Klis S. F. L., Vijverberg H. P. M., van den Bercken J. Phenylpyrazoles, a new class of pesticides: An electrophysiological investigation into basic effects. Pestic. Biochem. Physiol. 39:1991;210.
19. Shimazu A., Izawa N., Kurihara H., Inamori M., Horii T. Biological activity of phenyltriazole derivative and its effect on the nervous system. 1991;Abstracts of Papers, 35th Annual Meeting of Japanese Society of Applied Entomology and Zoology, Shizuoka. p. 173.
20. 35S]TBPS. Pestic. Biochem. Physiol. 47:1993;98.
21. 35S]t-Butylbicyclophosphorothionate binds with high affinity to brain-specific sites coupled to γ-aminobutyric acid-A and ion recognition sites. Mol. Pharmacol. 23:1983;326.
22. 3H]EBOB) in vertebrate brain and insect head. Pestic. Biochem. Physiol. 44:1992;1.
23. Bradford M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:1976;248.
24. + channel of insect nervous system identified by receptor sites for tetrodotoxin, and scorpion and sea anemone toxins. Biochem. Biophys. Res. Commun. 131:1985;1226.
25. Ray R., Morrow C. S., Catterall W. A. Binding of scorpion toxin to receptor sites associated with voltage-sensitive sodium channels in synaptic nerve ending particles. J. Biol. Chem. 253:1978;7307.
26. + channel: Alteration of its properties in pyrethroid-resistant flies. Biochemistry. 28:1989;1673.
27. 3H]batrachotoxinin A-20-α-benzoate binding by an N-alkylamide neurotoxin. Mol. Pharmacol. 36:1989;280.
28. Catterall W. A., Mollow C. S., Daly J. W., Brown G. B. Binding of batrachotoxinin A 20-α-benzoate to a receptor site associated with sodium channels in synaptic nerve ending particles. J. Biol. Chem. 256:1981;8922.
29. Deecher D. C., Soderlund D. M. RH 3421, an insecticidal dihydropyrazole, inhibits sodium channel-dependent sodium uptake in mouse brain preparations. Pestic. Biochem. Physiol. 39:1991;130.
30. Lombet A., Mourre C., Lazdunski M. Interaction of insecticides of the pyrethroid family with specific binding sites on the voltage-dependent sodium channel from mammalian brain. Brain Res. 459:1988;44.
31. Brown G. B., Gaupp J. E., Olsen R. W. Pyrethroid insecticides: Stereospecific allosteric interaction with the batrachotoxinin-A benzoate binding site of mammalian voltage-sensitive sodium channels. Mol. Pharmacol. 34:1988;54.
32. Hainzl D., Casida J. E. Fipronil insecticide: Novel photochemical desulfinylation with retention of neurotoxicity. Proc. Natl. Acad. Sci. USA. 93:1996;12764.
33. Hainzl D., Cole L. M., Casida J. E. Mechanisms for selective toxicity of fipronil insecticide and its sulfone metabolite and desulfinyl photoproduct. Chem. Res. Toxicol. 11:1998;1529.
34. Scott J. G., Wen Z. Toxicity of fipronil to susceptible and resistant strains of German cockroaches (Dictyoptera: Blattellidae) and house flies (Diptera: Muscidae). J. Econ. Entomol. 90:1997;1152.
35. Wolff M. A., Wingate V. P. M. Characterization and comparative pharmacological studies of a functional γ-aminobutyric acid (GABA) receptor cloned from the tobacco budworm, Heliothis virescens (Noctuidae: Lepidoptera). Invertebr. Neurosci. 3:1998;305.
36. Perret P., Sarda X., Wolff M., Wu T.-T., Bushey D., Goelder M. Interaction of non-competitive blockers within the γ-aminobutyric acid type A chloride channel using chemically reactive probes as chemical sensors for cysteine mutants. J. Biol. Chem. 274:1999;25350.
37. Akamatsu M., Ozoe Y., Ueno T., Fujita T., Mochida K., Nakamura T., Matsumura F. Sites of action of noncompetitive GABA antagonists in houseflies and rats: Three-dimensional QSAR analysis. Pestic. Sci. 49:1997;319.
38. Gant D. B., Chalmers A. E., Wolff M. A., Hoffman H. B., Bushey D. F. Fipronil: Action at the GABA receptor. Rev. Toxicol. 2:1998;147.
39. Hosie A. M., Aronstein K., Sattelle D. B., ffrench-Constant R. H. Molecular biology of insect neuronal GABA receptors. Trends Neurosci. 20:1997;578.
40. 3H]batrachotoxinin A 20-α-benzoate binding to mouse brain sodium channels. Pestic. Biochem. Physiol. 45:1993;130.
41. 3H]batrachotoxinin A 20-α-benzoate binding to mouse brain sodium channels by the dihydropyrazole insecticide RH 3421. Pestic. Biochem. Physiol. 41:1991;265.
42. Nagata K., Ikeda T., Honda H., Shono T. Suppression of voltage-gated sodium currents by the dihydropyrazole insecticide, DPX-JW062 in rat dorsal root ganglion neuronsm. J. Pesticide Sci. 23:1998;62.
43. K. Nagata, T. Shono, X. Zhao, and, T. Narahashi, Mode of action of indoxacarb at ion channel level, Abstracts of Papers, 24th Annual Meeting of Pesticide Science Society of Japan, Utsunomiya, Japan, 1999, Abstract A106.
44. A. Karasawa, K. Nagata, and, T. Shono, Effects of indoxacarb on GABA(A) receptor-channel complex in rat dorsal root ganglion neurons, Abstracts of Papers, 24th Annual Meeting of Pesticide Science Society of Japan, Utsunomiya, Japan, 1999, Abstract A107.