Insect Control: Biological and Synthetic Agents - Index of

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for control of stinkbugs in soybean) and other insecticides are also being developed with an aim of broadening the insecticidal spectrum of neonicotinoids and to replace WHO Class I products from older chemical classes (Elbert et al., 2008). In addition to the insecticidal properties of imidacloprid, a stress shield mode of action was identified. It supports plants in moderating the effects of abiotic and biotic stress. Therefore, Trimax Õ (Hopkins et al., 2005), an optimized imidacloprid formulation was developed, which moderates water stress in plants with an average lint yield increase in cotton of 10% (Thielert, 2006; Gonias et al., 2008). In addition to crop protection, applications of neonicotinoid insecticides in non-agricultural fields is also expanding in the last 5 years, e.g., household sectors, lawn and garden, and for controlling ectoparasites in animal health (Rust, 2005). New bait gel products containing imidacloprid like Maxforce Prime Õ (Bayer EnvironmentalSciences), for the control of cockroaches, and thiamethoxam like OptigardTM (Syngenta), for broad-spectrum control of ants, are now on the market. Other products include Agita Õ 10 WG (Novartis Animal Health), a watersoluble granule containing thiamethoxam and the fly pheromone (Z)-9-tricosen for use against the house fly Musca domestica and against synanthropic flies (Nurita et al., 2008). In the field of animal health, AdvantageMulti TM (or Advocate Õ ; Bayer Animal Health) is a spot-on formulation of the macrolactone moxidectin and imidacloprid which shows efficacy against ear mites (Otodectes cynotis) and fleas (Ctenocephalides felis) (Wenzel et al., 2008). K9 Advantix Õ (Bayer Animal Health) is a spot-on topical solution of imidacloprid and permethrin for dogs, that work synergistically against the most common and important external parasites such as the long star tick, like Amblyomma americanum. Finally, Vectra 3D TM (Summit Vet- Pharm) is a new topical spot-on ectoparasiticide containing a combination of dinotefuran, permethrin, and pyriproxyfen against A. americanum and the Gulf Coast tick A. maculatum on dogs (Coyne, 2009). Over the last 5 years, sales of the neonicotinoids have nearly trebled. Future expansion will be driven by growth of the established commercial neonicotinoids. The chemical class will further benefit from organophosphate and carbamate replacements. Generic competition will lead to price erosions, which also will open new opportunities for neonicotinoids in low-price markets (Elbert et al., 2008). Combined with active life-cycle management such as optimized formulations and new combinations, neonicotinoids will be the most important chemical class in the next few years in modern crop protection. References A3: Addendum 117 Baur, P., Arnold, R., Giessler, S., Mansour, P., Vermeer, R., 2007. Bioavailability of insecticides from O-TEQ Õ formulations: overcoming barriers for systemic active ingredients. Pflanzenschutz-Nachrichten Bayer (English edition) 60, 27–42. Brejc, K., van Dijk, W.J., Klaassen, R.V., Schurmans, M., van der Oost, J., Smit, A.B., Sixma, T.K., 2001. Crystal structure of an ACh-binding protein reveals the ligandbinding domain of nicotinic receptors. Nature 411, 269–276. Casida, J.E., Tomizawa, M., 2008. Insecticide interactions with g-aminobutyric acid and nicotinic receptors: predictive aspects of structural models. J. Pesticide Sci. 33, 4–8. Celie, P.H., Kasheverow, I.E., Mordvintsev, D.Y., Hogg, R.C., van Nierop, P., van Elk, R., van Rossum-Fikkert, S.E., Zhamak, M.N., Bertrand, D., Tsetlin, V., Sixma, T.K., Smit, A.B., 2005. Crystal structure of nicotinic acetylcholine receptor homologue AChBP in complex with an a-conotoxin PnIA variant. Nat. Struct. Mol. Biol. 12, 1–7. Coyne, M.J., 2009. Efficacy of a topical ectoparasiticide containing dinotefuran, pyriproxyfen, and permethrin against Amblyomma americanum (Lone Star Tick) and Amblyomma maculatum (Gulf Coast tick) on dogs. Vet. Ther. Res. Appl. Vet. Med. 10, 17–23. Elbert, A., Haas, M., Springer, B., Thielert, W., Nauen, R., 2008. Applied aspects of neonicotinoid uses in crop protection. Pest Manage. Sci. 64, 1099–1105. Gao, F., Mer, G., Tonelli, M., Hansen, S.B., Burghard, T.P., Taylor, P., et al., 2006. Solution NMR of acetylcholine binding protein reveals agonist-mediated conformational change of the C-loop. Mol. Pharmacol. 70, 1230–1235. Gonias, E.D., Oosterhuis, D.M., Bibi, A.C., 2008. Physiologic response of cotton to the insecticide imidacloprid under high-temperature stress. J. Plant Growth Regul. 27, 77–82. Gorman, K., Devine, D., Bennison, J., Coussons, P., Punchard, N., Denholm, I., 2007. Report of resistance to the neonicotinoid insecticide imidacloprid in Trialeurodes vaporariorum (Hemiptera: Aleyrodidae). Pest Manage. Sci. 63, 555–558. Gorman, K., Liu, Z., Brüggen, K.U., Nauen, R., 2008. Neonicotinoid resistance in rice brown planthopper, Nilaparvata lugens. Pest Manage. Sci. 64, 1122–1125. Hansen, S.B., Talley, T.T., Radic, Z., Taylor, P., 2004. Structural and ligand recognition characteristics of an acetylcholine-binding protein from Aplysia californica. J. Biol. Chem. 279, 24197–24202. Hopkins, J.A., Vodrazka, K., Rudolph, R., Bell, J., 2005. Trimax: assisting cotton growers in yield maximization. Proc. Beltwide Cotton Conf. 2644/1–2644/5. Horowitz, A.R., Kontsedalov, S., Ishaya, I., 2004. Dynamics of resistance to the neonicotinoids acetamiprid and thiamethoxam in Bemisia tabaci (Homoptera: Aleyrodidae). J. Econ. Entomol. 97, 2051–2056. Ihara, M., Brown, L.A., Ishida, C., Okuda, H., Sattelle, D.B., Matsuda, K., 2006. Actions of imidacloprid,
118 A3: Addendum clothianidin and related neonicotinoids on nicotinic acetylcholine receptors of American cockroach neurons and their relationships with insecticidal potency. J. Pestic. Sci. 31, 35–40. Ihara, M., Shimomura, M., Ishida, C., Nishiwaki, H., Akamatsu, M., Sattelle, D.B., Matsuda, K., 2007. A hypothesis to account for the selective and divers actions of neonicotinoid insecticides at their molecular targets, nicotinic acetylcholine receptors: catch and release in hydrogen bond networks. Invert. Neurosci. 7, 47–51. Jeschke, P., 2007a. Chemical structural features of commercial neonicotinoids. In: Krämer, W., Schirmer, U. (Eds.), Modern Crop Protection Compounds. Wiley- VCH, Weinheim, Germany, pp. 958–961. Jeschke, P., 2007b. Nicotinic acetylcholine receptors as a continous source for rational insecticides. In: Ishaaya, I., Nauen, R., Horowitz, A.R. (Eds.), Insecticides Design Using Advanced Technologies. Springer, Berlin- Heidelberg, Germany, pp. 151–195. Jeschke, P., Nauen, R., 2007. Thiamethoxam: a neonicotinoid precursor converted to clothianidin in insects and plants. In: Lyga, J.W., Theodoridis, G. (Eds.), Synthesis and Chemistry of Agrochemicals VII. ACS Symposium Series 948, Washigton, DC, pp. 51–65. Jeschke, P., Nauen, R., 2008. Neonicotinoids – from zero to hero in insecticide chemistry. Pest Manage. Sci. 64, 1084–1098. Karatolos, N., Gorman, K., Williamson, M., Nauen, R., Ffrench-Constant, R., Denholm, I., 2009. Resistance to neonicotinoid insecticides in the greenhouse whitefly, Trialeurodes vaporariorum. Intergr. Control Protect. Crops Mediterr. Clim. 49, 103–106. Karunker, I., Benting, J., Lueke, B., Ponge, T., Nauen, R., Roditakes, E., Vontas, J., Gorman, K., Morin, D.I.S., 2008. Over-expression of cytochrome P 450 CYP6CM1 is associated with high resistance to imidacloprid in the B and Q biotypes of Bemisia tabaci (Hemiptera: Aleyrodidae). Insect. Biochem. Mol. Biol. 38, 634–644. Karunker, I., Morou, E., Nikou, D., Nauen, R., Sertchook, R., Stevenson, B.J., Paine, M.J.I., Morin, S., Vontas, J., 2009. Structural model and functional characterization of the Bemisia tabaci CYP6CM1vQ, a cytochrome P 450 associated with high levels of imidacloprid resistance. Insect. Biochem. Mol. Biol. 39, 697–706. Kayser, H., Wellmann, H., Lee, C., Decock, A., Gomes, M., Cheek, B., Lind, R., Baur, M., Hattenschwiler, J., Maienfisch, P., 2007. Thiamethoxam: high-affinity binding and unusual mode of interference with other neonicotinoids at aphid membranes. In: Lyga, J.W., Theodoridis, G. (Eds.), Synthesis and Chemistry of Agrochemicals VII. ACS Symposium Series 948, Washigton, DC, pp. 67–81. Liu, Z., Williamson, M.S., Lansdell, S.J., Han, Z., Denholm, I., Millar, N.S., 2007. Target-site resistance to neonicotinoid insecticides in the brown planthopper Nilaparvata lugens. In: Ohkawa, H., Miyagawa, H., Lee, P.W. (Eds.), Pesticide Chemistry. Wiley-VCH, Weinheim, Germany, pp. 271–274. Liu, Z., Han, Z., Zhang, Y., Song, F., Yao, X., Liu, S., Gu, J., Millar, N.S., 2009. Heteromeric co-assembly of two insect nicotinic acetylcholine receptor a subunits: influence on sensitivity to neonicotinoid insecticides. J. Neurochem. 108, 498–506. Loso, M.R., Nugent, B.M., Huang, J.X., Rogers, R.B., Zhu, Y., Renga, J.M., Hegde, V., Demark, J.J., 2007. Insecticidal N-substituted (6-haloalkylpyridin-3yl)alkyl-sulfoximines. Pat. Appl. WO 095229 A2 (Dow AgroSciences LLC). Maienfisch, P., 2007. Six-membered heteroxycles (thiamethoxam, AKD 1022). In: Krämer, W., Schirmer, U. (Eds.), Modern Crop Protection Compounds. Wiley- VCH, Weinheim, Germany, pp. 994–1013. Matsuda, K., Shimomura, M., Ihara, M., Akamatsu, M., Sattelle, D.B., 2005. Neonicotinoids show selective and diverse actions on their nicotinic receptor targets: Electrophysiology, molecular biology, and receptor modeling studies. Biosci. Biotechnol. Biochem. 69, 1442–1452. Matsuda, K., Kanaoka, S., Akamatsu, M., Sattelle, D.B., 2009. Diverse actions and target-site selectivity of neonicotinoids: structural insights. Mol. Pharmacol. 76, 1–10. Matsumura, M., Takeuci, H., Satoh, M., Sanada- Morimura, S., Otuka, A., Watanabe, T., Van Thanh, D., 2008. Species-specific insecticide resistance to imidacloprid and fipronil in the rice planthoppers Nilaparvata lugens and Sogatella furcifera in East and South-east Asia. Pest Manage. Sci. 64, 1115–1121. McCaffery, A., Nauen, R., 2006. Insecticide resistance action committee (IRAC): public responsibility and enlightened industrial self-interest. Outlook Pest Manage. 17, 11–14. Miyagi, S., Komaki, I., Ozoe, Y., 2006. Identification of a high-affinity binding site for dinotefuran in the nerve cord of the American cockroach. Pest Manage. Sci. 62, 293–298. Nauen, R., Denholm, I., 2005. Resistance of insect pests to neonicotinoid insecticides: current status and future prospects. Arch. Insect Biochem. Physiol. 58, 200–215. Nauen, R., Bielza, P., Denholm, I., Gorman, K., 2008. Age specific expression of resistance to a neonicotinoid insecticide in the whitefly Bemisia tabaci. Pest Manage. Sci. 64, 1106–1110. Nurita, A.T., Abu Hassan, A., Nur Aida, H., Norasmah, B., 2008. Field evaluations of the granular fly bait, Quick Bayt and the paint-on fly bait, Agita against synanthropic flies. Trop. Biomed. 25, 126–133. Ohno, I., Tomizawa, M., Durkin, K.A., Naruse, Y., Casida, J., Kagabu, S., 2009. Molecular features of neonicotinoid pharmacophore variants interacting with insect nicotinic receptor. Chem. Res. Toxicol. 22, 476–482. Puinean, A.M., Denholm, I., Millar, N.S., Nauen, R., Williamson, M.S., 2009. Characterization of imidacloprid resistance mechanisms in the brown planthopper, Nilaparvata lugens Stal (Hemiptera: Delphacidae). Pestic.
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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
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4-position result in almost complet
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and their primary site of action is
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Figure 4 Folded and extended confor
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aromatic rings or methyl groups by
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pyrethroids) and consequently a sec
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1998), although the precise mechani
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polymorphisms in the protein. Of th
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observed resistance to pyrethroids,
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propoxur against Culex quinquefasci
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esistance in house fly. Insect Bioc
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Shan, G.M., Hammock, B.D., 2001. De
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A1.4. Resistance The increasing num
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B A IIS4-S5 linker, IIS5 helix and
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2 Indoxacarb and the Sodium Channel
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Figure 2 Structures of pyrazoline-l
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observed that both indoxacarb and i
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deflections resulting from stresses
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Figure 8 Dihydropyrazole block appe
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potential conduction in the CNS of
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known to affect blocker affinity, w
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Figure 13 Diagrammatic representati
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that the probable mechanism of ovil
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conventional chemistries and spinos
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Clare, J.J., Tate, S.N., Nobbs, M.,
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Tsurubuchi, Y., Karasawa, A., Nagat
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R1 N N O N H indoxacarb. Thus, whil
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3 Neonicotinoid Insecticides P Jesc
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esidues, like the pyrid-3-ylmethyl
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containing neonicotinoids, and neon
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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
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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 104 and 105: Table 7 Environmental profile of co
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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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Page 122 and 123: patterns in Colorado potato beetle
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Page 130 and 131: Biochem. Physiol., doi: 10.1016/j.p
Page 132 and 133: 4 Insect Growth- and Development-Di
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Page 136 and 137: Table 1 Bisacylhydrazine insecticid
Page 138 and 139: 4.2.2. Bisacylhydrazines as Tools o
Page 140 and 141: to the three EcRs with either muris
Page 142 and 143: of action of ecdysone agonists was
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Page 148 and 149: dipteran insects, like the midge, C
Page 150 and 151: eetle (Exomala orientalis) when app
Page 152 and 153: metabolic fate studies showed the i
Page 154 and 155: y specific proteins in signaling pa
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Page 158 and 159: can be reversed by applying JH. JH
Page 160 and 161: door for a more rational approach t
Page 162 and 163: apparent that it was a bHLH-PAS and
Page 164 and 165: Table 9 Continued Bemisia tabaci (s
Page 166 and 167: Table 11 Insect control with some a
Page 168 and 169: Table 13 Ecotoxicological profile o
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Page 172 and 173: The discovery of diflubenzuron spaw
Page 174 and 175: Table 15 Environmental effects of s
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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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