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Volumn 19, Issue 7, 2006, Pages 944-951

Chloropyridinyl neonicotinoid insecticides: Diverse molecular substituents contribute to facile metabolism in mice

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIPRID; ALKENE; AMIDE; AMINOGUANIDINE; ANABASINE DERIVATIVE; CARBENOID; CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; CHLOROPYRIDINYL NEONICOTINOID INSECTICIDE; GLUCURONIDE; GLYCINE; GUANIDINE; IMIDACLOPRID; IMIDAZOLE DERIVATIVE; IMINE; INSECTICIDE; NITENPYRAM; NITROSOGUANIDINE; SULFATE; THIACLOPRID; THIAZOLIDINE DERIVATIVE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33746211295     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0600696     Document Type: Article
Times cited : (153)

References (28)
  • 2
    • 50849123838 scopus 로고    scopus 로고
    • Tomlin, C. D. S., Ed., British Crop Protection Council, Alton, Hampshire, U.K.
    • Tomlin, C. D. S., Ed. (2003) The Pesticide Manual, 13th ed., British Crop Protection Council, Alton, Hampshire, U.K., pp 1344.
    • (2003) The Pesticide Manual , vol.13 , pp. 1344
  • 3
    • 0003141929 scopus 로고    scopus 로고
    • Chloronicotinyl insecticides-discovery, application and future perspective
    • Kagabu, S. (1997) Chloronicotinyl insecticides-discovery, application and future perspective. Rev. Toxicol. 1, 75-129.
    • (1997) Rev. Toxicol. , vol.1 , pp. 75-129
    • Kagabu, S.1
  • 4
    • 0037209233 scopus 로고    scopus 로고
    • Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors
    • Tomizawa, M., and Casida, J. E. (2003) Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors. Annu. Rev. Entomol. 48, 339-364.
    • (2003) Annu. Rev. Entomol. , vol.48 , pp. 339-364
    • Tomizawa, M.1    Casida, J.E.2
  • 5
    • 13844280231 scopus 로고    scopus 로고
    • Neonicotinoid insecticide toxicology: Mechanisms of selective action
    • Tomizawa, M., and Casida, J. E. (2005) Neonicotinoid insecticide toxicology: mechanisms of selective action. Annu. Rev. Pharmacol. Toxicol. 45, 247-268.
    • (2005) Annu. Rev. Pharmacol. Toxicol. , vol.45 , pp. 247-268
    • Tomizawa, M.1    Casida, J.E.2
  • 6
    • 13844300285 scopus 로고    scopus 로고
    • Imidacloprid; pesticide tolerances
    • Environmental Protection Agency (2003) Imidacloprid; pesticide tolerances. Federal Register 68, 35303-35315.
    • (2003) Federal Register , vol.68 , pp. 35303-35315
  • 7
    • 33746247549 scopus 로고    scopus 로고
    • Summary of toxicology testing for nitenpyram
    • in Japanese
    • Summary of toxicology testing for nitenpyram. (1998) J. Pestic. Sci. (in Japanese) 23, 73-77.
    • (1998) J. Pestic. Sci. , vol.23 , pp. 73-77
  • 8
    • 13844307083 scopus 로고    scopus 로고
    • Acetamiprid; pesticide tolerances
    • Environmental Protection Agency (2003) Acetamiprid; pesticide tolerances. Fed. Regist. 68, 52343-52353.
    • (2003) Fed. Regist. , vol.68 , pp. 52343-52353
  • 9
    • 13844320268 scopus 로고    scopus 로고
    • Thiacloprid; pesticide tolerances
    • Environmental Protection Agency (2003) Thiacloprid; pesticide tolerances. Fed. Regist. 68, 55503-55513.
    • (2003) Fed. Regist. , vol.68 , pp. 55503-55513
  • 12
    • 0042935994 scopus 로고    scopus 로고
    • Therapy and prevention of parasitic insects in veterinary medicine using imidacloprid
    • Mencke, N., and Jeschke, P. (2002) Therapy and prevention of parasitic insects in veterinary medicine using imidacloprid. Curr. Top. Med. Chem. 2, 701-715.
    • (2002) Curr. Top. Med. Chem. , vol.2 , pp. 701-715
    • Mencke, N.1    Jeschke, P.2
  • 13
    • 0012317834 scopus 로고    scopus 로고
    • Behaviour of thiacloprid (YRC 2894) in plants and animals
    • Klein, O. (2001) Behaviour of thiacloprid (YRC 2894) in plants and animals. Pflanzenschutz-Nachr. Bayer 54, 209-240.
    • (2001) Pflanzenschutz-Nachr. Bayer , vol.54 , pp. 209-240
    • Klein, O.1
  • 14
    • 33746186692 scopus 로고    scopus 로고
    • Novartis Animal Health Canada, Inc. (2003) Capstar Monograph. (http://www.ah.ca.novartis.com/product/capstarmono.html) (Accessed March, 2006).
    • (2003) Capstar Monograph
  • 15
    • 25444471829 scopus 로고    scopus 로고
    • Neonicotinoid nitroguanidine insecticide metabolites: Synthesis and nicotinic receptor potency of guanidines, aminoguanidines, and their derivatives
    • Kanne, D. B., Dick, R. A., Tomizawa, M., and Casida, J. E. (2005) Neonicotinoid nitroguanidine insecticide metabolites: synthesis and nicotinic receptor potency of guanidines, aminoguanidines, and their derivatives. Chem. Res. Toxicol. 18, 1479-1484.
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 1479-1484
    • Kanne, D.B.1    Dick, R.A.2    Tomizawa, M.3    Casida, J.E.4
  • 16
    • 0029789274 scopus 로고    scopus 로고
    • Novel neonicotinoidagarose affinity column for Drosophila and Musca nicotinic acetylcholine receptors
    • Tomizawa, M., Latli, B., and Casida, J. E. (1996) Novel neonicotinoidagarose affinity column for Drosophila and Musca nicotinic acetylcholine receptors. J. Neurochem. 67, 1669-1676.
    • (1996) J. Neurochem. , vol.67 , pp. 1669-1676
    • Tomizawa, M.1    Latli, B.2    Casida, J.E.3
  • 17
    • 85008571646 scopus 로고
    • Synthesis and insecticidal activity of acyclic nitroethene compounds containing a heteroarylmethylamino group
    • Minamida, I., Iwanaga, K., Tabuchi, T., Aoki, I., Fusaka, T., Ishizuka, H., and Okauchi, T. (1993) Synthesis and insecticidal activity of acyclic nitroethene compounds containing a heteroarylmethylamino group. J. Pestic. Sci. 18, 41-48.
    • (1993) J. Pestic. Sci. , vol.18 , pp. 41-48
    • Minamida, I.1    Iwanaga, K.2    Tabuchi, T.3    Aoki, I.4    Fusaka, T.5    Ishizuka, H.6    Okauchi, T.7
  • 18
    • 31844451913 scopus 로고    scopus 로고
    • Substrate specificity of rabbit aldehyde oxidase for nitroguanidine and nitromethylene neonicotinoid insecticides
    • Dick, R. A., Kanne, D. B., and Casida, J. E. (2006) Substrate specificity of rabbit aldehyde oxidase for nitroguanidine and nitromethylene neonicotinoid insecticides. Chem. Res. Toxicol. 19, 38-43.
    • (2006) Chem. Res. Toxicol. , vol.19 , pp. 38-43
    • Dick, R.A.1    Kanne, D.B.2    Casida, J.E.3
  • 19
    • 0033577991 scopus 로고    scopus 로고
    • Novel and potent 6-chloro-3-pyridinyl ligands for the α4β2 neuronal nicotinic acetylcholine receptor
    • Latli, B., D'Amour, K., and Casida, J. E. (1999) Novel and potent 6-chloro-3-pyridinyl ligands for the α4β2 neuronal nicotinic acetylcholine receptor. J. Med. Chem. 42, 2227-2234.
    • (1999) J. Med. Chem. , vol.42 , pp. 2227-2234
    • Latli, B.1    D'Amour, K.2    Casida, J.E.3
  • 20
    • 0037142378 scopus 로고    scopus 로고
    • Structural features of azidopyridinyl neonicotinoid probes conferring high affinity and selectivity for mammalian α4β2 and Drosophila nicotinic receptors
    • Zhang, N., Tomizawa, M., and Casida, J. E. (2002) Structural features of azidopyridinyl neonicotinoid probes conferring high affinity and selectivity for mammalian α4β2 and Drosophila nicotinic receptors. J. Med. Chem. 45, 2832-2840.
    • (2002) J. Med. Chem. , vol.45 , pp. 2832-2840
    • Zhang, N.1    Tomizawa, M.2    Casida, J.E.3
  • 21
    • 13844294285 scopus 로고    scopus 로고
    • Identification of aldehyde oxidase as the neonicotinoid nitroreductase
    • Dick, R. A., Kanne, D. B., and Casida, J. E. (2005) Identification of aldehyde oxidase as the neonicotinoid nitroreductase. Chem. Res. Toxicol. 18, 317-323.
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 317-323
    • Dick, R.A.1    Kanne, D.B.2    Casida, J.E.3
  • 22
    • 0038338722 scopus 로고    scopus 로고
    • The neonicotinoid electronegative pharmacophore plays the crucial role in the high affinity and selectivity for the Drosophila nicotinic receptor: An anomaly for the nicotinoid cation-π interaction model
    • Tomizawa, M., Zhang, N., Durkin, K. A., Olmstead, M. M., and Casida, J. E. (2003) The neonicotinoid electronegative pharmacophore plays the crucial role in the high affinity and selectivity for the Drosophila nicotinic receptor: an anomaly for the nicotinoid cation-π interaction model. Biochemistry 42, 7819-7827.
    • (2003) Biochemistry , vol.42 , pp. 7819-7827
    • Tomizawa, M.1    Zhang, N.2    Durkin, K.A.3    Olmstead, M.M.4    Casida, J.E.5
  • 23
    • 22344448525 scopus 로고    scopus 로고
    • 14C]-acetamiprid in six biological compartments of the honeybee, Apis mellifera L
    • 14C]-acetamiprid in six biological compartments of the honeybee, Apis mellifera L. Pest. Manage. Sci. 61, 742-748.
    • (2005) Pest. Manage. Sci. , vol.61 , pp. 742-748
    • Brunet, J.-L.1    Badiou, A.2    Belzunces, L.P.3
  • 24
    • 0010430683 scopus 로고
    • The house fly metabolism of nitromethylene insecticides
    • (Shankland, D. L., Hollingworth, R. M., and Smyth, T., Jr., Eds.), Plenum Press, New York
    • Reed, W. T., and Erlam, G. J. (1978) The house fly metabolism of nitromethylene insecticides. In Pesticide and Venom Neurotoxicity (Shankland, D. L., Hollingworth, R. M., and Smyth, T., Jr., Eds.) pp 159-169, Plenum Press, New York.
    • (1978) Pesticide and Venom Neurotoxicity , pp. 159-169
    • Reed, W.T.1    Erlam, G.J.2
  • 25
    • 0036739990 scopus 로고    scopus 로고
    • Neonicotinoid insecticides: Reduction and cleavage of imidacloprid nitroimine substituent by liver microsomal and cytosolic enzymes
    • Schulz-Jander, D. A., Leimkuehler, W. M., and Casida, J. E. (2002) Neonicotinoid insecticides: reduction and cleavage of imidacloprid nitroimine substituent by liver microsomal and cytosolic enzymes. Chem. Res. Toxicol. 15, 1158-1165.
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 1158-1165
    • Schulz-Jander, D.A.1    Leimkuehler, W.M.2    Casida, J.E.3
  • 26
    • 0037035949 scopus 로고    scopus 로고
    • Imidacloprid insecticide metabolism: Human cytochrome P450 isozymes differ in selectivity for imidazolidine oxidation versus nitroimine reduction
    • Schulz-Jander, D. A., and Casida, J. E. (2002) Imidacloprid insecticide metabolism: human cytochrome P450 isozymes differ in selectivity for imidazolidine oxidation versus nitroimine reduction. Toxicol. Lett. 132, 65-70.
    • (2002) Toxicol. Lett. , vol.132 , pp. 65-70
    • Schulz-Jander, D.A.1    Casida, J.E.2
  • 27
    • 29044440259 scopus 로고    scopus 로고
    • Neonicotinoid metabolic activation and inactivation established with coupled nicotinic receptor-CYP3A4 and aldehyde oxidase systems
    • Honda, H., Tomizawa, M., and Casida, J. E. (2006) Neonicotinoid metabolic activation and inactivation established with coupled nicotinic receptor-CYP3A4 and aldehyde oxidase systems. Toxicol. Lett. 161, 108-114.
    • (2006) Toxicol. Lett. , vol.161 , pp. 108-114
    • Honda, H.1    Tomizawa, M.2    Casida, J.E.3
  • 28
    • 0035891562 scopus 로고    scopus 로고
    • Analgesic and toxic effects of neonicotinoid insecticides in mice
    • Tomizawa, M., Cowan, A., and Casida, J. E. (2001) Analgesic and toxic effects of neonicotinoid insecticides in mice. Toxicol. Appl. Pharmacol. 177, 77-83.
    • (2001) Toxicol. Appl. Pharmacol. , vol.177 , pp. 77-83
    • Tomizawa, M.1    Cowan, A.2    Casida, J.E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.