Insect Control: Biological and Synthetic Agents - Index of

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R1 N N O N H indoxacarb. Thus, while providing important pielectron interactions for local anesthetics, the aromatic residue at Y20 in D4S6 might hinder access of SCBIs to their binding site. In the German cockroach sodium channel variant BgNav1-1A, alanine substitution at positions F13 and Y20 of D4S6 had somewhat different effects on the action of SCBIs (Silver et al., 2009a). F13A substitution in the cockroach channel did not change its sensitivity to indoxacarb or DCJW, and made it hypersensitive to metaflumizone. Furthermore, this mutation greatly accelerated recovery of the channels from block by metaflumizone. Therefore, in contrast to its role in the rat Nav1.4 channel in the binding of LAs and SCBIs, the phenyl functional group at position F13 in D4S6 does not appear to participate in the binding of SCBIs in BgNav1-1A channels, and may in fact hinder the access of metaflumizone (but not DCJW) to its binding site. As mentioned above, alanine substitution of Y20 in D4S6 of rat Nav1.4 sodium channels increased sensitivity to DCJW 58fold (Silver and Soderlund, 2007). The corresponding mutation increased the sensitivity of BgNa v1-1A channels 13-fold to DCJW and 11-fold to metaflumizone. Thus, the aromatic side chain at position 20 of D4S6, while crucial for local anesthetic binding, does not appear to participate in binding interactions with SCBIs, and in fact seems to hinder access of SCBIs to their binding site in both insect and mammalian sodium channels. In conclusion, while F13 of D4S6 is important for binding of both LAs and SCBIs in the rat Na v1.4 channel, it does not affect binding of DCJW in the BgNav1-1A channel, and in fact hinders access of metaflumizone to the binding site. Y20 in D4S6, while crucial for LA binding, hinders access of SCBIs to their site in both insect and mammalian channels. The fact that residues involved in local anesthetic binding sometimes antagonize binding of SCBIs suggests that the SCBI and LA binding R2 3-phenyl 1-phenylcarbamoyl- 2-pyrazolines R1 N N O N H R3 R2 3,4-diphenyl 1-phenylcarbamoyl- 2-pyrazolines Figure A1 Chemical evolution of the semicarbazone metaflumizone from pyrazolines. sites overlap, but that the binding energy of SCBIs comes in part from different residues, which have yet to be identified. References CF 3 N NH O N H metaflumizone A2: Addendum 59 CN OCF 3 BASF Agricultural Products, 2007. Metaflumizone Worldwide Technical Brochure. Li, H.-L., Galue, A., Meadows, L., Ragsdale, D.S., 1999. A molecular basis for the different local anesthetic affinities of resting versus open and inactivated states of the sodium channel. Mol. Pharmacol. 55, 134–141. Rugg, D., Hair, J.A., 2007. Dose determination of a novel formulation of metaflumizone plus amitraz for the treatment and control of fleas (Ctenocephalides felis) and ticks (Rhipicephalus sanguineus) on dogs. Vet. Parasitol. 150, 203–208. Salgado, V.L., Hayashi, J.H., 2007. Metaflumizone is a novel sodium channel blocker insecticide. Vet. Parasitol. 150, 182–189. Silver, K.S., Soderlund, D.M., 2005. State-dependent block of rat Nav1.4 sodium channels expressed in Xenopus oocytes by pyrazoline-type insecticides. Neurotoxicology 26, 397–406. Silver, K.S., Soderlund, D.M., 2007. Point mutations at the local anesthetic receptor site modulate the statedependent block of rat Na v1.4 sodium channels by pyrazoline-type insecticides. Neurotoxicology 28, 655–663. Silver, K.S., Nomura, Y., Salgado, V.L., Dong, K., 2009a. Role of the sixth transmembrane segment of domain IV of the cockroach sodium channel in the action of sodium channel blocker insecticides. Neurotoxicology 30, 613–621. Silver, K.S., Song, W., Nomura, Y., Salgado, V.L., Dong, K., 2009b. Mechanism of action of sodium channel blocker insecticides (SCBIs) on insect sodium channels. Pestic. Biochem. Physiol. in press, doi:10.1016/ j.pestbp.2009.09.001. Song, W., Liu, Z., Dong, K., 2006. Molecular basis of differential sensitivity of insect sodium channels to DCJW, a bioactive metabolite of the oxadiazine insecticide indoxacarb. Neutotoxicol 27, 237–244.
60 A2: Addendum Takagi, K., Hamaguchi, H., Nishimatsu, T., Konno, T., 2007. Discovery of metaflumizone, a novel semicarbazone insecticide. Vet. Parasitol. 150, 177–181. von Stein, R.T., Soderlund, D.M., 2009. A point mutation that enhances slow sodium channel inactivation confers resting-state sensitivity to block by sodium channel blocker insecticides (SCBIs). Program No. 314.7/B58. 2009 Neuroscience Meeting Planner. Society for Neuroscience, Chicago, IL, Online. Zhao, X., Ikeda, T., Salgado, V.L., Yeh, J.Z., Narahashi, T., 2005. Block of two subtypes of sodium channels in cockroach neurons by indoxacarb insecticides. Neurotoxicology 26, 455–465.
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INSECT CONTROL BIOLOGICAL AND SYNTH
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INSECT CONTROL BIOLOGICAL AND SYNTH
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CONTENTS Preface vii Contributors i
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PREFACE When Elsevier published the
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J T Andaloro E. I. Du Pont de Nemou
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1 Pyrethroids B P S Khambay and P J
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activity. In contrast to most other
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Figure 1 Commercial and novel pyret
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Figure 2 Pyrethroids referred to in
Page 20 and 21: 4-position result in almost complet
Page 22 and 23: and their primary site of action is
Page 24 and 25: Figure 4 Folded and extended confor
Page 26 and 27: aromatic rings or methyl groups by
Page 28 and 29: pyrethroids) and consequently a sec
Page 30 and 31: 1998), although the precise mechani
Page 32 and 33: polymorphisms in the protein. Of th
Page 34 and 35: observed resistance to pyrethroids,
Page 36 and 37: propoxur against Culex quinquefasci
Page 38 and 39: esistance in house fly. Insect Bioc
Page 40 and 41: Shan, G.M., Hammock, B.D., 2001. De
Page 42 and 43: A1.4. Resistance The increasing num
Page 44 and 45: B A IIS4-S5 linker, IIS5 helix and
Page 46 and 47: 2 Indoxacarb and the Sodium Channel
Page 48 and 49: Figure 2 Structures of pyrazoline-l
Page 50 and 51: observed that both indoxacarb and i
Page 52 and 53: deflections resulting from stresses
Page 54 and 55: Figure 8 Dihydropyrazole block appe
Page 56 and 57: potential conduction in the CNS of
Page 58 and 59: known to affect blocker affinity, w
Page 60 and 61: Figure 13 Diagrammatic representati
Page 62 and 63: that the probable mechanism of ovil
Page 64 and 65: conventional chemistries and spinos
Page 66 and 67: Clare, J.J., Tate, S.N., Nobbs, M.,
Page 68 and 69: Tsurubuchi, Y., Karasawa, A., Nagat
Page 72 and 73: 3 Neonicotinoid Insecticides P Jesc
Page 74 and 75: esidues, like the pyrid-3-ylmethyl
Page 76 and 77: containing neonicotinoids, and neon
Page 78 and 79: Studies were also done using compar
Page 80 and 81: Becke, 1988; Klamt, 1995) level of
Page 82 and 83: sampling using forcefield methods (
Page 84 and 85: Figure 9 Stable conformations and p
Page 86 and 87: Figure 13 Binding to putative catio
Page 88 and 89: Figure 14 Systemicity of neonicotin
Page 90 and 91: site (Kayser et al., 2002). Clothia
Page 92 and 93: Figure 20 Important pest insects ta
Page 94 and 95: Barley yellow dwarf virus vectors s
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Page 98 and 99: within the desensitized state over
Page 100 and 101: the accumulation of this acid in th
Page 102 and 103: 3.8.1. Safety Profile The introduct
Page 104 and 105: Table 7 Environmental profile of co
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Page 108 and 109: imidacloprid conferring a high leve
Page 110 and 111: nAChR are comparable to the efficac
Page 112 and 113: Figure 25 Flea control achieved wit
Page 114 and 115: and the resolution of FAD was teste
Page 116 and 117: Brown, J.K., Perring, T.M., Cooper,
Page 118 and 119: In: Ishaaya, I. (Ed.), Biochemical
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Léna, C., Changeux, J.-P., 1993. A
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patterns in Colorado potato beetle
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nach Saatgutbeizung. Pflanzenschutz
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Today, photoaffinity labeling (e.g.
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for control of stinkbugs in soybean
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Biochem. Physiol., doi: 10.1016/j.p
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4 Insect Growth- and Development-Di
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The molting process is initiated by
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Table 1 Bisacylhydrazine insecticid
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4.2.2. Bisacylhydrazines as Tools o
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to the three EcRs with either muris
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of action of ecdysone agonists was
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thus inducing effects and symptomol
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and microsomes. Subsequently, Willi
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dipteran insects, like the midge, C
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eetle (Exomala orientalis) when app
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metabolic fate studies showed the i
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y specific proteins in signaling pa
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their reduced risk for the environm
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can be reversed by applying JH. JH
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door for a more rational approach t
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apparent that it was a bHLH-PAS and
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Table 9 Continued Bemisia tabaci (s
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Table 11 Insect control with some a
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Table 13 Ecotoxicological profile o
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Flucycloxuron Nonsystemic acaricide
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The discovery of diflubenzuron spaw
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Table 15 Environmental effects of s
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ecessive (R male S female) manner,
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esistance management programs due t
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IPS Paraconfusus lanier (Coleoptera
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larvae parasitized by Microplitis r
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Kostyukovsky, M., Chen, B., Atsmi,
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Three-dimensional quantitative stru
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Riddiford, L.M., 1994. Cellular and
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characterization of resistant clone
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Biological Approaches to Pest Contr
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M389 L308 M272 T304 T393 V404 L420
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5 Azadirachtin, a Natural Product i
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and Hemiptera and was related to ef
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eported, but this is rather nonspec
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important source of pest control at
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effects with physiological effects
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eing associated with an accumulatio
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et al., 1992). Salehzadeh et al. (2
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ehavior of Spodoptera littoralis (p
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indica A. Juss. IBH Publishing Comp
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Smith, S.L., Mitchell, M.J., 1988.
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which interact directly with azadir
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6 The Spinosyns: Chemistry, Biochem
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Table 1 Structures of the spinosyns
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Table 2 Biological activity of spin
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A large synthetic effort has gone i
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216 6: The Spinosyns: Chemistry, Bi
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Figure 4 Spinosad metabolism in avi
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A6 Addendum: The Spinosyns T C Spar
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246 A6: Addendum Scott, 2008) and i
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248 7: Bacillus thuringiensis: Mech
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A7 Addendum: Bacillus thuringiensis
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280 A7: Addendum toxins is magnitud
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Table 1 Comparative properties of s
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286 8: Mosquitocidal B. sphaericus:
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Table 4 Characteristics of various
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A8 Addendum: Bacillus sphaericus Ta
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310 A8: Addendum essential to devel
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314 9: Insecticidal Toxins from Pho
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A9 Addendum: Recent Advances in Pho
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330 A9: Addendum Lee, S.C., Stoilov
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332 10: Genetically Modified Baculo
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384 A10: Addendum cysteine protease
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388 11: Entomopathogenic Fungi and
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Zare, R., Gams, W., Culham, A., 200
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434 A11: Addendum although a number
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436 A11: Addendum Examination of ge
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440 12: Insect Transformation for U
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448 A12: Addendum genetic transform
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452 Subject Index Aphis gossypii (c
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454 Subject Index Bisacylhydrazine
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456 Subject Index Cry toxins (conti
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458 Subject Index Entomopathogenic
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460 Subject Index Homoptera molting
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462 Subject Index Kinoprene (ENSTAR
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464 Subject Index Muscle(s) sodium
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466 Subject Index Photorhabdus (con
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468 Subject Index Sodium channel bl
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470 Subject Index Toxocara cati, im
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