Neonicotinoids - From zero to hero in insecticide chemistry

Pest Management Science

Volumn 64, Issue 11, 2008, Pages 1084-1098

  Jeschke, Peter ^a   Nauen, Ralf ^a  

^a BAYER CROPSCIENCE AG   (Germany)

Author keywords

Bioisosteric segments; Insecticides; Neonicotinoid; Nicotinic acetylcholine receptors; Pharmacophore model; Resistance; Selectivity

Indexed keywords

INSECTICIDE; NICOTINIC AGENT;

CROP PROCESSING; INSECT; INSECTICIDE; INTEGRATED PEST MANAGEMENT;

ANIMAL; CHEMISTRY; INSECT; INSECT CONTROL; INSECTICIDE RESISTANCE; REVIEW;

ANIMALS; INSECT CONTROL; INSECTICIDE RESISTANCE; INSECTICIDES; INSECTS; NICOTINIC AGONISTS;

HEXAPODA;

EID: 55849119810     PISSN: 1526498X     EISSN: 15264998     Source Type: Journal    
DOI: 10.1002/ps.1631     Document Type: Review

References (130)

1. Nauen R and Bretschneider T, New modes of action of insecticides. Pestic Outlook 12:241-245 (2002).
2. Bai D, Lummis SCR, Leicht W, Breer H and Satelle DB, Actions of imidacloprid and related nitromethylene on cholinergic receptors of an identified insect motor neuron. Pestic Sci 33:197-204 (1991).
3. Yamamoto I, Neonicotinoids: mode of action and selectivity. Agrochem Japan 68:14-15 (1996).
4. Chao SL, Dennehy TJ and Casida JE, Whitefly (Hemiptera: Aleyrodidae) binding site for imidacloprid and related insecticides: a putative nicotinic acetylcholine receptor. J Econ Entomol 90:879-882 (1997).
5. 3H]imidacloprid binding site. J Neurochem 75:1294-1303 (2000).
6. Denholm I, Devine G, Foster S, Gorman K and Nauen R, Incidence and management of insecticide resistance to neonicotinoids. Proc Brighton Crop Prot Conf - Pests and Diseases, BCPC, Farnham, Surrey, UK, pp. 161-168 (2002).
7. Nauen R and Denholm I, Resistance of insect pests to neonicotinoid insecticides: current status and future prospects. Arch Ins Biochem Physiol 58:200-215 (2005).
8. Feuer H and Lawrence JP, The alkyl nitrate nitration of active methylene compounds. 6. A new synthesis of α-nitroalkyl heterocyclics. J Am Chem Soc 91:1856-1857 (1969).
9. Soloway SB, Henry AC, Kollmeyer WD, Padgett WM, Powell JE, Roman SA, et al, Nitromethylene heterocycles as insecticides, in Pesticide and Venom Neurotoxicology, ed. by Shankland DL, Hollingworth RMand Smyth T, Jr. Plenum, New York, NY, pp. 153-158 (1978).
10. Soloway SB, Henry AC, Kollmeyer WD, Padgett WM, Powell JE, Roman SA, et al, Nitromethylene insecticides. Adv Pestic Sci, Plenary Lect Symp Pap Int Congr Pestic Chem, 4th Meeting 2: 206-217 (1979).
11. Kollmeyer WD, Flattum RF, Foster JP, Powell JE, Schroeder ME and Soloway S, Discovery of the nitromethylene heterocycle insecticides, in Neonicotinoid Insecticides and the Nicotinic Acetylcholine Receptor, ed. by Yamamoto I and Casida JE. Springer, New York, NY, pp. 71-89 (1999).
12. Kagabu S, Molecular design of neonicotinoids: past, present and future, in Chemistry of Crop Protection: Progress and Prospects in Science and Regulation, ed. by Voss G and Ramos G. Wiley-VCH, New York, NY, pp. 193-212 (2003).
13. Schroeder ME and Flattum RF, The mode of action and neurotoxic properties of the nitromethylene heterocyclic insecticides. Pestic Biochem Physiol 22:148-160 (1984).
14. Sattelle DB, Buckingham SD, Wafford KA, Sherby SM, Bakry NM, Eldefrawi LT, et al, Actions of the insecticide 2-(nitromethylene)-tetrahydro-1,3- thiazine on insect and vertebrate nicotinic acetylcholine receptors. Proc R Soc Lond B Biol Sci 237:501-514 (1989).
15. Kagabu S and Medej S, Stability comparison of imidacloprid and related compounds under simulated sunlight, hydrolysis conditions, and to oxygen. Biosci Biotechnol Biochem 59:980-985 (1995).
16. Kagabu S, Chloronicotinyl insecticides: discovery, application and future perspective. Rev Toxicol 1:75-129 (1997).
17. Sone S, Yamada Y and Tsuboi S, New pesticide screening method for leafhoppers and planthoppers using rice seedlings. Jap J Appl Entomol Zool 39:171-173 (1995).
18. Elbert A, Overbeck H, Iwaya K and Tsuboi S, Imidacloprid, a novel systemic nitromethylene analog insecticide for crop protection. Proc Brighton Crop Prot Conf - Pests and Diseases, BCPC, Farnham, Surrey, UK, pp. 21-28 (1990).
19. Elbert A, Becker B, Hartwig J and Erdelen C, Imidacloprid: a new systemic insecticide. Pflanzenschutz-Nachrichten Bayer 44:113-136 (1990).
20. Elbert A, Erdelen C, Kühnhold J, Nauen R and Schmidt HW, Thiacloprid, a novel neonicotinoid insecticide for foliar application. Proc Brighton Crop Prot Conf - Pests and Diseases, BCPC, Farnham, Surrey, UK, pp. 21-26 (2000).
21. Mencke N and Jeschke P, Therapy and prevention of parasitic insects in veterinarymedicine using imidacloprid. Curr Topics Med Chem 2:701-715 (2002).
22. Jeschke P, Moriya K, Lantzsch R, Seifert H, Lindner W, Jelich K, et al, Thiacloprid (Bay YRC2894) - a new member of the chloronicotinyl insecticide (CNI) family. Pflanzenschutz-Nachrichten Bayer 54:147-160 (2001).
23. Senn R, Hofer D, Hoppe T, Angst M,Wyss P, Brandl F, et al, CGA293343: a novel broad-spectrum insecticide supporting sustainable agriculture worldwide. Proc Brighton Crop Prot Conf - Pests and Diseases, BCPC, Farnham, Surrey, UK, pp. 27-36 (1998).
24. Minamida I, Iwanaga K, Tabuchi T, Aoki I, Fusaka T, Ishizuka H, et al, Synthesis and insecticidal activity of acyclic nitroethene compounds containing a heteroarylmethylamino group. J Pestic Sci 18:41-48 (1993).
25. Takahashi H, Mitsui J, Takakusa N, Matsuda M, Yoneda H, Suzuki J, et al, NI-25, a new type of systemic and broad spectrum insecticide. Proc Brighton Crop Prot. Conf - Pests and Diseases, BCPC, Farnham, Surrey, UK, pp. 89-96 (1992).
26. Ohkawara Y, Akayama A, Matsuda K and Andersch W, Clothianidin: a novel broad spectrum neonicotinoid insecticide. Proc BrightonCrop ProtConf - Pests and Diseases, BCPC, Farnham, Surrey, UK, pp. 51-58 (2002).
27. Jeschke P, Uneme H, Benet-Buchholz J, Stölting J, Sirges W, Beck ME, et al, Clothianidin (TI-435) - the third member of the chloronicotinyl insecticide (CNI™) family. Pflanzenschutz-Nachrichten Bayer 56:5-24 (2003).
28. Uneme H, Konobe M, Akayama A, Yokota T and Mizuta K, Discovery and development of a novel insecticide 'Clothianidin'. Sumitomo Kagaku (Osaka, Japan) 2:20-33 (2006).
29. Kodaka K, Kinoshita K,Wakita T, Kawahara N and Yasui N, MTI-446: a novel systemic insect control compound. Proc Brighton Crop Prot Conf - Pests and Diseases, BCPC, Farnham, Surrey, UK, pp. 21-26 (1998).
30. Wakita T, Yasui N, Yamada E and Kishi D, Development of a novel insecticide, dinotefuran I. J Pestic Sci (Tokyo, Japan) 30:122-123 (2005).
31. Wakita T, Yasui N, Yamada E and Kishi D, Development of a novel insecticide, dinotefuran II. J Pestic Sci (Tokyo, Japan) 30:133-138 (2005).
32. Wollweber D and Tietjen K, Chloronicotinyl insecticides: a success of the new chemistry, in Neonicotinoid Insecticides and the Nicotinic Acetylcholine Receptor, ed. by Yamamoto I and Casida JE. Springer, New York, NY, pp. 109-125 (1999).
33. Nauen R, Ebbinghaus-Kintscher U, Elbert A, Jeschke P and Tietjen K, Acetylcholine receptors as sites for developing neonicotinoid insecticides, in Biochemical Sites of Insecticide Action and Resistance, ed. by Ishaaya I. Springer, New York, NY, pp. 77-105 (2001).
34. Jeschke P and Nauen R, Neonicotinoid insecticides, in Comprehensive Molecular Insect Science, Vol. 5, ed. by Gilbert LI, Iatrou L and Gill SS. Elsevier, Oxford, UK, pp. 53-105 (2005).
35. Jeschke P, Chemical structural features of commercial neonicotinoids, in Modern Crop Protection Compounds, ed. by Krämer W and Schirmer U. Wiley-VCH, Weinheim, Germany, pp. 958-961 (2007).
36. Tomizawa M, Lee DL and Casida JE, Neonicotinoid insecticides: molecular features conferring selectivity for insect versus mammalian nicotinic receptors. J Agric Food Chem 48:6016-6024 (2000).
37. Jeschke P, Schindler M and Beck M, Neonicotinoid insecticides: retrospective consideration and prospects. Proc Brighton Crop Prot Conf - Pests and Diseases, BCPC, Farnham, Surrey, UK, pp. 137-144 (2002).
38. Kagabu S, Moriya K, Shibuya K, Hattori Y, Tsuboi S and Shiokawa K, 1-(6-Halonicotinyl)-2-nitromethylene-imidazolidines as potential new insecticides. Biosci Biotechnol Biochem 56:362-363 (1992).
39. Moriya K, Shibuya K, Hattori Y, Tsuboi S, Shiokawa K and Kagabu K, 1-(6-Chloronicotinyl)-2-nitroimino-imidazolidines and related compounds as potential new insecticides. Biosci Biotechnol Biochem 56:364-365 (1992).
40. Moriya K, Shibuya K, Hattori Y, Tsuboi S, Shiokawa K and Kagabu S, 1-Diazinylmethyl-2-nitromethylene- and 2-nitroimino-imidazolidines as new potential insecticides. J Pestic Sci (International Edition) 18:119-123 (1993).
41. Tabuchi T, Fusaka T and Iwanaga K, Studies on acyclic nitroethene compounds. 3. Synthesis and insecticidal activity of acyclic nitroethene compounds containing 6-substituted-3-pyridylamino group. J Pestic Sci 19:119-125 (1994).
42. Nakayama A, Molecular similarity and structure activity relationship of neonicotinoid insecticides. J Pestic Sci 23:336-343 (1998).
43. Nakayama A and Sukekawa M, Quantitative correlation between molecular similarity and receptor binding activity of neonicotinoid insecticides. Pestic Sci 52:104-110 (1998).
44. Okazawa A, Akamatsu M, Ohoka A, Nishiwaki H, Cho WJ, Nakagawa Y, et al, Prediction of the binding mode of imidacloprid and related compounds to housefly head acetylcholine receptors using three-dimensional QSAR analysis. Pestic Sci 54:134-144 (1998).
45. Yamamoto I, Tomizawa M, Saito T, Miyamoto T, Walcott EC and Sumikawa K, Structural factors contributing to insecticidal and selective actions of neonicotinoids. Arch Insect Biochem Physiol 37:24-32 (1998).
46. Tomizawa Mand Yamamoto I, Structure activity relationships of neonicotinoids and imidacloprid analogues. J Pestic Sci 18:91-98 (1993).
47. Leicht W, Imidacloprid: a chloronicotinyl insecticide. Pestic Outlook 4:17-24 (1993).
48. Maienfisch P, Brandl F, Kobel W, Rindlisbacher A and Senn R, CGA293,343: a novel, broad-spectrum neonicotinoid insecticide, in: Neonicotinoid Insecticides and the Nicotinic Acetylcholine Receptor, ed. by Yamamoto I and Casida JE. Springer, New York, NY, pp. 177-209 (1999).
49. Wakita T, Konoshita K, Yamada E, Yasui N, Kawahara N, Naoi A, et al, The discovery of dinotefuran: a novel neonicotinoid. Pest Manag Sci 59:1016-1022 (2003).
50. Maienfisch P, Huerlimann H, Rindlisbacher A, Gsell L, Dettwilwer H, Haettenschwiler J, et al, The discovery of thiamethoxam: a second generation neonicotinoid. Pest Manag Sci 57:165-176 (2001).
51. Cascio M, Structure and function of the glycine receptor and related nicotinoid receptors. J Biol Chem 279:19383-19386 (2004).
52. Celie PHN, van Rossum-Fikkert SE, van Dijk WJ, Brejc K, Smit AB and Sixma TK, Nicotine and carbamylcholine binding to nicotinic acetylcholine receptors as studied in AChBP crystal structure. Neuron 41:907-914 (2004).
53. Jeschke P and Nauen R, Nicotinic acetylcholine receptor agonists, target and selectivity aspects, in Modern Crop Protection Compounds, ed. by Krämer W and Schirmer U. Wiley-VCH, Weinheim, Germany, pp. 927-958 (2007).
54. Kalamida D, Poula K, Avramopoulou V, Fostieri E, Lagoumintzis G, Lazaridis K, et al, Muscle and neuronal nicotinic acetylcholine receptors. Structure, function and pathogenicity. FEBS Journal 274:3799-3845 (2007).
55. Brejc K, van Dijk WJ, Klaassen RV, Schurmans M, van der Oost J, Smit AB, et al, Crystal structure of an ACh-binding protein reveals the ligand-binding domain of nicotinic receptors. Nature (London) 411:269-276 (2001).
56. Smit AB, Syed NI, Schaap D, van Minnen J, Klumperman J, Kits KS, et al, A glia-derived acetylcholine binding protein that modulates synaptic transmission. Nature (London) 411:261-268 (2001).
57. Hansen SB, Talley TT, Radic Z and Taylor P, Structural and ligand recognition characteristics of an acetylcholine-binding protein from Aplysia californica. J Biol Chem 279:24197-24202 (2004).
58. Celie PH, Kasheverow IE, Mordvintsev DY, Hogg RC, van Nierop P, van Elk R, et al, Crystal structure of nicotinic acetylcholine receptor homologue AChBP in complex with an α-conotoxin PnIA variant. Nat Struct Mol Biol 12:582-588 (2005).
59. Unwin N, Refined structure of the nicotinic acetylcholine receptor at 4 Å resolution. J Mol Biol 346:967-989 (2005).
60. Talley TT and Taylor P, Acetylcholine binding protein (AChBP) as soluble surrogate of the extracellular ligand binding domain of nicotinic acetylcholine receptors (nAChRs). Abstract of Papers, 232nd ACS National Meeting, San Francisco, CA, 10-14 September, MEDI-491 (2006).
61. Jeschke P, Nicotinic acetylcholine receptors as a continuous source for rational insecticides, in Insecticides Design Using Advanced Technologies, ed. by Ishaaya I, Nauen R and Horowitz AR. Springer, Berlin-Heidelberg, Germany, pp. 151-195 (2007).
62. Tomizawa M, Maltby D, Medzihradszky KF and Casida JE, Defining nicotinic agonist binding surface through photoaffinity labeling. Biochemistry 46:8798-8806 (2007).
63. Tomizawa M, Talley TT, Maltby D, Durkin KA, Medzihradszky KF, Burlingame AL, et al, Mapping the exclusive neonicotinoid binding site. ProcNat Acad SciUSA 104:9075-9080 (2007).
64. Gao F, Mer G, Tonelli M, Hansen SB, Burghardt TP, Taylor P, et al, Solution NMR of acetylcholine binding protein reveals agonist-mediated conformational change of the Cloop. Mol Pharmacol 70:1230-1235 (2006).
65. Shimomura M,Okuda H, Matsuda K, Komai K, Akamatsu M and Sattelle DB, Effects of mutations of a glutamine residue in loop D of the α7 nicotinic acetylcholine receptor on agonist profiles for neonicotinoid insecticides and related ligands. Brit J Pharmacol 137:162-169 (2002).
66. Shimomura M, Yokata M, Okumura M, Matsuda K, Akamatsu M, Sattelle DB, et al, Combinatorial mutations in loops D and F strongly influence responses of the α7 nicotinic acetylcholine receptor imidacloprid. Brain Res 991:71-77 (2003).
67. Wang Y, Cheng J, Qian X and Zhong Li, Bioorg Med Chem 15:2624-2630 (2007).
68. Shimomura M, Yokota M, Ihara M, Akamatsu M, Sattelle DB and Matsuda K, Role of the selectivity of neonicotinoids of insect-specific basic residues in loop D of the nicotinic acetylcholine receptor agonist binding site. Mol Pharm 70:1255-1263 (2006).
69. Shimomura M, Matsuda K, Akamatsu M, Sattelle DB and Komai K, Responses to neonicotinoids of chicken α7 nicotinic acetylcholine receptors: effects of mutations of isoleucine 191 in loop F to aromatic residues. J Pestic Sci 29:364-368 (2004).
70. Glennon RA, Dukat Mand Liao L, Musings on α4β2 nicotinic acetylcholine (nACh) receptor pharmacophor model. Curr Topics Med Chem 4:631-644 (2004).
71. Beers WH and Reich E, Structure and activity of acetylcholine. Nature (London) 225:917-922 (1970).
72. Zhang N, Tomizawa M and Casida JE, α-Nitro ketone as an electrophile and nucleophile: synthesis of 3-substituted 2- nitromethylenetetrahydrothiophene and -tetrahydrofuran as Drosophila nicotinic receptor probes. J Org Chem 69:876-881 (2004).
73. Graton J, Berthelot M, Gal JF, Laurence C, Lebreton J, Le Questel JY, et al, The nicotinic pharmacophore: thermodynamics of the hydrogen-bonding complexation of nicotine, nornicotine, and models.J OrgChem68:8208-8221 (2003).
74. Amri S, Sansom MSP and Biggin PC, Molecular dynamics studies of AChBP with nicotine and carbamoylcholine: the role of water in the binding pocket. Protein Engineering, Design and Selection 20:353-359 (2007).
75. Kagabu S, Studies on the synthesis and insecticidal activity of neonicotinoid compounds. J Pestic Sci 21:237-239 (1996).
76. Koyanagi T and Haga T, Bioisosterism in agrochemicals, in Synthesis and Chemistry of Agrochemicals IV, ed. by Baker R, Fenyes JG and Basarab GS. ACS, Washington, DC, pp. 15-24 (1995).
77. Okazawa A, Akamatsu M, Nishiwaki H, Nakagawa Y, Miyagawa H, Nishimura K, et al, Three-dimensional quantitative structure activity relationship analysis of acyclic and cyclic chloronicotinyl insecticides. Pest Manag Sci 56:509-515 (2000).
78. Ihara M, Matsuda K, Shimomura M, Sattelle DB and Komai K, Super agonist actions of clothianidin and related compounds on the SADβ2 nicotinic acetylcholine receptor expressed in Xenopus laevis oocytes. Biosci Biotechnol Biochem 68:761-763 (2004).
79. Brown LA, Ihara M, Buckingham SD, Matsuda K and Sattelle DB, Neonicotinoid insecticides display partial and super agonist actions on native insect nicotinic acetylcholine receptors. J Neurochem 99:608-615 (2006).
80. Ihara M, Mechanism of action of insecticides on ligand-gated ion channels. J Pestic Sci 32:278-280 (2007).
81. Kagabu S and Akagi T, Quantum chemical consideration of photostability of imidacloprid and related compounds. J Pest Sci 22:84-89 (1997).
82. Briggs G, Bromilow RH and Evans AA, Relationships between lipophilicity and root uptake and translocation of nonionized chemicals by barley. Pestic Sci 13:495-504 (1982).
83. Elbert A and Nauen R, New applications for neonicotinoid insecticides using imidacloprid as an example, in Novel Approaches to Insect Pest Management in Field and Protected Crops, ed. by Horowitz AR and Ishaaya I. Springer, New York, NY, pp. 29-44 (2004).
84. Elbert A, Becker B, Hartwig J and Erdelen C, Imidacloprid: a new systemic insecticide. Pflanzenschutz-Nachrichten Bayer 44:113-136 (1991).
85. Elbert A, Nauen R and Leicht W, Imidacloprid, a novel chloronicotinyl insecticide, biological activity and agricultural importance, in Insecticides with Novel Modes of Action, Mechanism and Application, ed. by Ishaaya I and Degheele D. Springer, New York, NY, pp. 50-73 (1998).
86. Yamamoto I, Nicotine to neonicotinoids: 1962-1997, in Neonicotinoid Insecticides and the Nicotinic Acetylcholine Receptor, ed. by Yamamoto I and Casida JE. Springer, New York, NY, pp. 3-27 (1999).
87. Knaust HJ and Poehling HM, Studies of the action of imidacloprid on grain aphids and their efficiency to transmit BYD virus. Pflanzenschutz- Nachrichten Bayer 45:381-408 (1992).
88. Roberts TR and Hutson TH (eds) Metabolic Pathways of Agrochemicals, Part 2, Insecticides and Fungicides. Cambridge University Press, Cambridge, UK (1999).
89. Tomizawa M and Casida JE, Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors. Annu Rev Entomol 48:339-364 (2003).
90. Greenwood R, Ford MG and Scarr A, Neonicotinoid pharmacokinetics. Proc Brighton Crop Prot Conf - Pests and Diseases, BCPC, Farnham, Surrey, UK, pp. 153-160 (2002).
91. Nauen R, Ebbinghaus-Kintscher U, Salgado VL and Kaussmann M, Thiamethoxam is a neonicotinoid precursor converted to clothianidin in insects and plants. Pestic Biochem Physiol 76:55-69 (2003).
92. Jeschke P and Nauen R, Thiamethoxam: a neonicotinoid precursor converted to clothianidin in insects and plants, in Synthesis and Chemistry of Agrochemicals VII, ed. by Lyga JW and Theodoridis G. ACS, Washington, DC, pp. 51-65 (2007).
93. 3H]thiamethoxam in Myzus persicae and Aphis craccivora. Pest Manag Sci 60:959-970 (2004).
94. 3H]imidacloprid displacement in Myzus persicae and Aphis craccivora. Pest Manag Sci 60:945-958 (2004).
95. Methfessel C, Action of imidacloprid on the nicotinic acetylcholine receptor in rat muscle. Pflanzenschutz-Nachrichten Bayer 45:369-380 (1992).
96. Tomizawa M and Casida JE, Structure and diversity of insect nicotinic acetylcholine receptors. Pest Manag Sci 57:914-922 (2001).
97. Matsuda K, Buckingham SD, Kleier D, Rauh JJ, Grauso M and Sattelle DB, Neonicotinoids: insecticides acting on insect nicotinic acetylcholine receptors. Trends Pharmacol Sci 22:573-580 (2001).
98. 3H] imidacloprid in the insect acetylcholine receptor. Pestic Biochem Physiol 46:40-46 (1993).
99. Matsuda K, Shimomura M, Ihara M, Akamatsu M and Sattelle DB, Neonicotinoids show selective and diverse actions on their nicotinic receptor targets: electrophysiology, molecular biology, and receptor modeling studies. Biosci Biotechnol Biochem 69:1442-1452 (2005).
100. Tomizawa M and Casida JE, Neonicotinoid insecticide toxicology: mechanisms of selective action. Annu Rev Pharmacol Toxicol 45:247-268 (2005).
101. Yamamoto I, Yabuta G, Tomizawa M, Saito T, Miyamoto T and Kagabu S, Molecular mechanisms for selective toxicity of nicotinoids and neonicotinoids. J Pestic Sci 20:33-40 (1995).
102. Arias HR, Topology of ligand binding sites on the nicotinic acetylcholine receptor. Brain Res Rev 25:133-191 (1992).
103. Tomizawa M and Casida JE, Minor structural changes in neonicotinoid insecticides confer differential subtype selectivity for mammalian nicotinic acetylcholine receptors. Brit J Pharmacol 127:115-122 (1999).
104. Tomizawa M and Casida JE, Structure and diversity of insect nicotinic acetylcholine receptors. Pest Manag Sci 57:914-922 (2001).
105. Debnath B, Gayen S, Naskar SK, Roy K and Jha T, Quantitative structure-activity relationship study on some azidopyridinyl neonicotinoid insecticides for their selective affinity towards the Drosophila nicotinic receptor over mammalian α4β2 receptor using electrotopological state atom index. Drug Des Discov 18:81-89 (2003).
106. Basu A, Gayen S, Samanta S, Panda P, Srikanth K and Jha T, QSAR modeling of neonicotinoid insecticides for their selective affinity towards Drosophila nicotinic receptors over mammalian α4β2 receptors. Can J Chem 84:458-463 (2006).
107. Tomizawa M, Zhang N, Durkin KA, Olmstead MM and Casida JE, 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).
108. Cahill M, Gorman K, Day S, Denholm I, Elbert A and Nauen R, Baseline determination and detection of resistance to imidacloprid in Bemisia tabaci (Homoptera: Aleyrodidae). Bull Entomol Res 86:343-349 (1996).
109. Elbert A, Nauen R, Cahill M, Devonshire AL, Scarr AW, Sone S, et al, Resistance management with chloronicotinyl insecticides using imidacloprid as an example. Pflanzenschutz-Nachrichten Bayer 49:5-53 (1996).
110. Elbert A and Nauen R, Bioassays for imidacloprid for a resistance monitoring against the whitefly Bemisia tabaci. Proc Brighton Crop Prot Conf - Pests and Diseases, BCPC, Farnham, Surrey, UK, pp. 731-738 (1996).
111. Foster SP, Denholm I and Thompson R, Variation in response to neonicotinoid insecticides in peach-potato aphids, Myzus persicae (Hemiptera: Aphididae). Pest Manag Sci 59:166-173 (2003).
112. Nauen R, Stumpf N and Elbert A, Toxicological and mechanistic studies on neonicotinoid cross resistance in Q-type Bemisia tabaci (Hemiptera: Aleyrodidae). Pest Manag Sci 58:868-875 (2002).
113. Rauch N and Nauen R, Biochemical markers linked to neonicotinoid cross-resistance in Bemisia tabaci (Hemiptera: Aleyrodidae). Arch Insect Biochem Physiol 54:165-176 (2003).
114. Weichel I and Nauen R, Monitoring of insecticide resistance in damson hop aphids, Phorodon humuli Schrank (Hemiptera: Aphididae), from German hop gardens. Pest Manag Sci 59:991-998 (2003).
115. Ihara M, Shimimura M, Ishida C, Nishiwaki H, Akamatsu M, Sattelle DB, et al, A hypothesis to account for the selective and diverse actions of neonicotinoid insecticides at their molecular targets, nicotinic acetylcholine receptors: catch and release in hydrogen bond networks. Invertebrate Neurosci 7:47-51 (2007).
116. Nauen R, Strobel J, Tietjen K, Otsu Y, Erdelen C and Elbert A, Aphicidal activity of imidacloprid against a tobacco feeding strain of Myzus persicae and highly resistant to carbamates and organophosphates. Bull Entomol Res 86:165-171 (1996).
117. Devine G, Harling Z, Scarr AW and Devonshire AL, Lethal and sublethal effects of imidacloprid on nicotine-tolerant Myzus nicotianae and Myzus persicae. Pestic Sci 48:57-62 (1996).
118. Olsen ER, Dively GP and Nelson JO, Baseline susceptibility to imidacloprid and cross resistance patterns in Colorado potato beetle (Coleoptera: Chrysomelidae) populations. J Econ Entomol 93:447-458 (2000).
119. Zhao JZ, Bishop BA and Graphius EJ, Inheritance and synergism of resistance to imidacloprid in the Colorado potato beetle (Coleoptera: Chrysomelidae). J Econ Entomol 93:447-458 (2000).
120. Hollingworth RM, Mota-Sanchez D, Whalon ME and Graphius E, Comparative pharmacokinetics of imidacloprid in susceptible and resistant Colorado potato beetle. Proc 10th IUPAC International Congress on Chemistry of Crop Protection, Basel, Switzerland, p. 312 (2002).
121. Zhao JY, Liu W, Brown JM and Knowles CO, Insecticide resistance in field and laboratory strains of western flower thrips (Thysanoptera: Thripidae). J Econ Entomol 88:1164-1170 (1995).
122. Wen ZMand Scott JG, Cross resistance to imidacloprid strains of German cockroach (Blattella germanica) and housefly (Musca domestica). Pestic Sci 49:367-371 (1997).
123. Daborn P, Boundy S, Yen J, Pittendrigh B and ffrench-Constant R, DDT resistance in Drosophila correlates with Cyp6g1 over-expression and confers cross-resistance to the neonicotinoid imidacloprid. Mol Genet Genom 266:556-563 (2001).
124. Dennehy TJ and Russel JS, Susceptibility of Lygus bug populations in Arizona to acephate (Orthene) and bifenthrin (Capture) with related contrasts of other insecticides. Proc Beltwide Cotton Conf, Nashville, TN, Vol. 2, pp. 771-776 (1996).
125. Zewen L, Zhaojun H, Yinchang W, Lingchun Z, Hongwei Z and Chengjun L, Selection for imidacloprid resistance in Nilaparvata lugens: cross resistance patterns and possible mechanisms. Pest Manag Sci 59:1355-1359 (2003).
126. Byrne FJ, Castle S, Prabhaker N and Toscano NC, Biochemical study of resistance to imidacloprid in B biotype Bemisia tabaci from Guatemala. Pest Manag Sci 59:347-352 (2003).
127. Horowitz AR, Kontsedalov S and Ishaaya I, Dynamics of resistance to the neonicotinoids acetamiprid and thiamethoxam in Bemisia tabaci (Homoptera: Aleyrodidae). J Econ Entomol 97:2051-2056 (2004).
128. Elbert A, Schleiermacher B, Brueggen KU, Nauen R, Rogers D, Steffens R, et al, Bayer CropScience guidelines on resistance management for neonicotinoids. Pflanzenschutz-Nachrichten Bayer 58:5-32 (2005).
129. Grutter T, Le Nov̀ere N and Changeux JP, Rational understanding of nicotinic receptors drug binding. Curr Topics Med Chem 4:645-651 (2004).
130. Sine SM, Wang HL and Gao F, Toward atomic-scale understanding of ligand recognition in the muscle nicotinic receptor. Curr Med Chem 11:559-567 (2004).