Léna, C., Changeux, J.-P., 1993. Allosteric modulations <strong>of</strong> the nicotinic acetylcholine receptor. Trends Neurosci. 16, 181–186. Li, Y., Dennehy, T.J., Li, S., Wigert, M.E., Zarborac, M., et al., 2001. Sustaining Arizona’s fragile success in whitefly resistance management. In: Proc. Beltwide Cotton Conferences, National Cotton Council, Memphis, TN, pp. 1108–1114. Li, Y., Dennehy, T.J., Li, X., Wigert, M.E., 2000. Susceptibility <strong>of</strong> Arizona whiteflies to chloronicotinyl insecticides <strong>and</strong> IGRs: new developments in the 1999 season. In: Proc. Beltwide Cotton Conferences, National Cotton Council, Memphis, TN, pp. 1325–1330. Lind, R.J., Clough, M.S., Reynolds, S.E., Earley, F.G.P., 1998. [ 3 H]Imidaclorid labels high- <strong>and</strong> low-affinity nicotinic acetylcholine receptor-like binding sites in the aphid Myzus persicae (Hemiptera: Aphididae). Pestic. Biochem. Physiol. 62, 3–14. Liu, M.-Y., Casida, J.E., 1993a. High affinity binding <strong>of</strong> [ 3 H]imidacloprid in the insect acetylcholine receptor. Pestic. Biochem. Physiol. 1993, 40–46. Liu, M.-Y., Lanford, J., Casida, J.E., 1993b. Relevance <strong>of</strong> [ 3 H]imidacloprid binding site in housefly head acetylcholine receptor to insecticidal activity <strong>of</strong> 2-nitromethylenen- <strong>and</strong> 2-nitroimino-imidazolidines. Pestic. Biochem. Physiol. 46, 200–206. Liu, M.-Y., Latli, B., Casida, J.E., 1995. Imidacloprid binding site in Musca nicotinic acetylcholine receptor: interactions with physostigmine <strong>and</strong> a varity <strong>of</strong> nicotinic agonists with chloropyridyl <strong>and</strong> chlorothiazolyl substituents. Pestic. Biochem. Physiol. 52, 170–181. Maienfisch, P., Angst, M., Br<strong>and</strong>l, F., Fischer, W., H<strong>of</strong>er, D., et al., 2001a. Chemistry <strong>and</strong> biology <strong>of</strong> thiamethoxam: a second generation neonicotinoid. Pest Mgt Sci. 57, 906–913. Maienfisch, P., Br<strong>and</strong>l, F., Kobel, W., Rindlisbacher, A., Senn, R., 1999a. CGA 293,343: a novel, broad-spectrum neonicotinoid insecticide. In: Yamamoto, I., Casida, J.E. (Eds.), Neonicotinoid insecticides <strong>and</strong> the Nicotinic Acetylcholine Receptor. Springer, New York, pp. 177–209. Maienfisch, P., Gonda, J., Jacob, O., Kaufmann, L., Pitterna, T., et al., 1997. In: 214th Am. Chem. Soc. Natl Mtg Abstracts, Agro-018. Maienfisch, P., Gsell, L., Rindlisbacher, A., 1999b. Synthesis <strong>and</strong> insecticidal activity <strong>of</strong> CGA 293343: a novel broad-spectrum insecticide. Pestic. Sci. 55, 351–355. Maienfisch, P., Haettenschwiler, J., Rindlisbacher, A., Decock, A., Wellmann, H., et al., 2003. Azido-neonicotinoids as c<strong>and</strong>idate photoaffinity probes for insect nicotinic acetylcholine receptors. 1. Chimia 57, 710–714. Maienfisch, P., Huerlimann, H., Haettenschwiler, J., 2000. A novel method for the preparation <strong>of</strong> N,N 0 -disubstituted-N 00 -nitroguanidines, including a practical synthesis <strong>of</strong> the neonicotinoid insecticide clothianidin. Tetrahedron Lett. 41, 7187–7191. Maienfisch, P., Huerlimann, H., Rindlisbacher, A., Gsell, L., Dettwiler, H., et al., 2001b. The discovery <strong>of</strong> thiamethoxam: a second generation neonicotinoid. Pest Mgt Sci. 57, 165–176. 3: Neonicotinoid <strong>Insect</strong>icides 109 Maienfisch, P., Rindlisbacher, A., Huerlimann, H., Haettenschwiler, J., Desai, A.K., et al., 2002. 4-Nitroimino-1,3,5-oxadiazines: a new type <strong>of</strong> neonicotinoid insecticides. ACS Symp. Series 800, 219–230. Malgorzata, G., Mikolajczyk, M.S., O’Reilly, K.L., 2000. Clinical disease in kittens inoculated with a pathogenic strain <strong>of</strong> Bartonella henselae. Am. J. Vet. Res. 61, 375–379. Marshall, J., Buckingham, S.D., Shingai, R., Lunt, G.G., Goosey, M.W., et al., 1990. Sequence <strong>and</strong> functional expression <strong>of</strong> a single a subunit <strong>of</strong> an insect nicotinic acetylcholine receptor. EMBO J. 9, 4391–4398. Martinez-Torres, D., Foster, S.P., Field, L.M., Devonshire, A.L., Williamson, M.S., 1998. A sodium channel point mutation is associated with resistance to DDT <strong>and</strong> pyrethroid insecticides in the peach potato aphid, Myzus persicae (Sulzer) (Hemiptera: Aphididae). <strong>Insect</strong> Mol. Biol. 8, 1–8. Matsuda, K., Buckingham, S.D., Freeman, J.C., Squire, M.D., Baylis, H.A., et al., 1998. Effects <strong>of</strong> the a subunit on imidacloprid sensitivity <strong>of</strong> recombinant nicotinic acetylcholine receptors. Br. J. Pharmacol. 123, 518–524. Matsuda, K., Buckingham, S.D., Freeman, J.C., Squire, M.D., Baylis, H.A., et al., 1999. Role <strong>of</strong> the a subunit <strong>of</strong> nicotinic acetylcholine receptor in the selective action <strong>of</strong> imidacloprid. Pestic. Sci. 55, 211–213. Matsuda, K., Buckingham, S.D., Kleier, D., Rauh, J.J., Grauso, M., et al., 2001. Neonicotinoids: insecticides acting on insect nicotinic acetylcholine receptors. Trends Pharmacol. Sci. 22, 573–578. Matsuda, M., Takahashi, H., 1996. Mospilan (acetamiprid, NI-25): a new systemic insecticide. Agrochem. Japan 68, 12–20. McKenzie, J.A., 1996. Ecological <strong>and</strong> Evolutionary Aspects <strong>of</strong> <strong>Insect</strong>icide Resistance. Academic Press, San Diego, CA. Mehlhorn, H., D’Haese, J., Mencke, N., Hanssen, O., 2001b. In vivo <strong>and</strong> in vitro effects <strong>of</strong> imidacloprid on sheep keds (Melophagus ovinus): a light <strong>and</strong> electron microscopic study. Parasitol. Res. 87, 331–336. Mehlhorn, H., Hansen, O., Mencke, N., 2001a. Comparative study on the effects <strong>of</strong> three insecticides (fipronil, imidacloprid, selamectin) on the developmental stages <strong>of</strong> the cat flea (Ctenocephalides felis Buche 1835): a light <strong>and</strong> electron microscopic analysis <strong>of</strong> in vivo <strong>and</strong> in vitro experiments. Parasitol. Res. 87, 198–207. Mehlhorn, H., Mencke, N., Hansen, O., 1999. Effects <strong>of</strong> imidacloprid on adult <strong>and</strong> larval stages <strong>of</strong> the cat flea Ctenocephalides felis after in vivo <strong>and</strong> in vitro experiments: a light- <strong>and</strong> electronmicroscopy study. Parasitol. Res. 85, 625–637. Mehlhorn, H., Schmahl, G., Mencke, N., Bach, T., 2003. The effect <strong>of</strong> an imidacloprid <strong>and</strong> permethrin combination against developmental stages <strong>of</strong> Ixodes ricinus ticks. Parasitol. Res. 90, 119–121. Mencke, N., Jeschke, P., 2002. Therapy <strong>and</strong> prevention <strong>of</strong> parasitic insects in veterinary medicine using imidacloprid. Curr. Topics Med. Chem. 2, 701–715.
110 3: Neonicotinoid <strong>Insect</strong>icides Mencke, N., Volf, P., Volv<strong>of</strong>a, V., Stanneck, D., 2003. Repellent efficacy <strong>of</strong> a combination containing imidacloprid <strong>and</strong> permethrin against s<strong>and</strong> flies (Phlebotomus papatasi) on dogs. Parasitol. Res. 90, 108–111. Minamida, I., Iwanaga, K., Tabuchi, T., Aoki, I., Fusaka, T., et al., 1993. Synthesis <strong>and</strong> insecticidal activity <strong>of</strong> acylic nitroethene compounds containing a heteroarylmethylamino group. J. Pestic. Sci. 18, 41–48. Moores, G.D., Devine, G.J., Devonshire, A.L., 1994a. <strong>Insect</strong>icide-insensitive acetylcholinesterase can enhance esterase-based resistance in Myzus persicae <strong>and</strong> Myzus nicotianae. Pestic. Biochem. Physiol. 49, 114–120. Moores, G.D., Devine, G.J., Devonshire, A.L., 1994b. <strong>Insect</strong>icide resistance due to insensitive acetylcholinesterase in Myzus persicae <strong>and</strong> Myzus nicotianae. In: Proc. Brighton Crop Protection Conference: Pests <strong>and</strong> Diseases, vol. 1. pp. 413–418. Mori, K., Okumoto, T., Kawahara, N., Ozoe, Y., 2001. Interaction <strong>of</strong> dinotefuran <strong>and</strong> its analogues with nicotinic acetylcholine receptors <strong>of</strong> cockroach nerve cords. Pest Mgt Sci. 58, 190–196. Moriya, K., Shibuya, K., Hattori, Y., Tsuboi, S., Shiokawa, K., et al., 1992. 1-(6-Chloronicotinyl)-2nitroimino-imidazolidines <strong>and</strong> related compounds as potential new insecticides. Biosci. Biotechnol. Biochem. 56, 364–365. Moriya, K., Shibuya, K., Hattori, Y., Tsuboi, S., Shiokawa, K., et al., 1993. Structural modification <strong>of</strong> the 6-chloropyridyl moiety in the imidacloprid skeleton: introduction <strong>of</strong> a five-membered heteroaromatic ring <strong>and</strong> the resulting insecticidal activity. Biosci. Biotech. Biochem. 57, 127–128. Mutero, A., Pralavorio, M., Bride, J.M., Fournier, D., 1994. Resistance-associated point mutations in insecticide insensitive acetylcholinesterase. Proc. Natl Acad. Sci. USA 91, 5922–5926. Nagata, K., Aistrup, G.L., Song, J.-H., Narahashi, T., 1996. Subconductance-state currents generated by imidacloprid at the nicotinic acetylcholine receptor in PC 12 cells. NeuroReport 7, 1025–1028. Nakayama, A., 1998. Molecular similarity <strong>and</strong> structure– activity relationship <strong>of</strong> neonicotinoid insecticides. J. Pestic. Sci. 23, 336–343. Nakayama, A., Sukekawa, M., 1998. Quantitative correlation between molecular similarity <strong>and</strong> receptorbinding activity <strong>of</strong> neonicotinoid insecticides. Pestic. Sci. 52, 104–110. Nauen, R., Bretschneider, T., 2002. New modes <strong>of</strong> action <strong>of</strong> insecticides. Pestic. Outlook 12, 241–245. Nauen, R., Ebbinghaus, U., Tietjen, K., 1999a. Lig<strong>and</strong>s <strong>of</strong> the nicotinic acetylcholine receptor as insecticides. Pestic. Sci. 55, 608–610. Nauen, R., Ebbinghaus-Kintscher, A., Elbert, A., Jeschke, P., Tietjen, K., 2001. Acetylcholine receptors as sites for developing neonicotinoid insecticides. In: Iishaaya, I. (Ed.), Biochemical Sites <strong>of</strong> <strong>Insect</strong>icide Action <strong>and</strong> Resistance. Springer, New York, pp. 77–105. Nauen, R., Ebbinghaus-Kintscher, U., Salgado, V.L., Kaussmann, M., 2003. Thiamethoxam is a neonicotinoid precursor converted to clothianidin in insects <strong>and</strong> plants. Pest. Biochem. Physiol. 76, 55–69. Nauen, R., Elbert, A., 1997. Apparent tolerance <strong>of</strong> a fieldcollected strain <strong>of</strong> Myzus nicotianae to imidacloprid due to strong antifeeding response. Pestic. Sci. 49, 252–258. Nauen, R., Elbert, A., 2000. Resistance <strong>of</strong> Bemisia spp. (Homoptera: Aleyrodidae) to insecticides in southern spain with special reference to neonicotinoids. Pest Mgt Sci. 56, 60–64. Nauen, R., Elbert, A., 2003. European monitoring <strong>of</strong> resistance to common classes <strong>of</strong> insecticides in Myzus persicae <strong>and</strong> Aphis gossypii (Homoptera: Aphididae) with special reference to imidacloprid. Bull. Entomol. Res. 93, 47–54. Nauen, R., Hungenberg, H., Tollo, B., Tietjen, K., Elbert, A., 1998a. Antifeedant-effect, biological efficacy <strong>and</strong> high affinity binding <strong>of</strong> imidacloprid to acetylcholine receptors in tobacco associated Myzus persicae (Sulzer) <strong>and</strong> Myzus nicotianae Blackman (Homoptera: Aphididae). Pestic. Sci. 53, 133–140. Nauen, R., Reckmann, U., Armborst, S., Stupp, H.P., Elbert, A., 1999b. Whitefly-active metabolites <strong>of</strong> imidacloprid: biological efficacy <strong>and</strong> translocation in cotton plants. Pestic. Sci. 55, 265–271. Nauen, R., Strobel, K., Tietjen, K., Otsu, Y., 1996. Aphicidal activity <strong>of</strong> imidacloprid against a tobacco feeding strain <strong>of</strong> Myzus persicae (Homoptera: Aphididae) from Japan closely related to Myzus nicotianae <strong>and</strong> highly resistant to carbamates <strong>and</strong> organophosphates. Bull. Entomol. Res. 86, 165–171. Nauen, R., Stumpf, N., Elbert, A., 2002. Toxicological <strong>and</strong> mechanistic studies on neonicotinoid cross resistance in Q-type Bemisia tabaci (Hemiptera: Aleyrodidae). Pest Mgt Sci. 58, 868–875. Nauen, R., Tietjen, K., Wagner, K., Elbert, A., 1998b. Efficacy <strong>of</strong> plant metabolites <strong>of</strong> imidacloprid against Myzus persicae <strong>and</strong> Aphis gossypii (Homoptera: Aphididae). Pestic. Sci. 52, 53–57. Nishimura, K., K<strong>and</strong>a, Y., Okazawa, A., Ueno, T., 1994. Relationship between insecticidal <strong>and</strong> neurophysiological activities <strong>of</strong> imidacloprid <strong>and</strong> related compounds. Pestic. Biochem. Physiol. 50, 51–59. Ohkawara, Y., Akayama, A., Matsuda, K., Andersch, W., 2002. Clothianidin: a novel broad-spectrum neonicotinoid insecticide. In: Proc. Brighton Crop Protection Conference: Pests <strong>and</strong> Diseases, vol. 1. pp. 51–58. Okazawa, A., Akamatsu, M., Nishiwaki, H., Nakagawa, Y., Miyagawa, H., et al., 2000. Three-dimensional quantitative structure–activity relationship analysis <strong>of</strong> acyclic <strong>and</strong> cyclic chloronicotinyl insecticides. Pest Mgt Sci. 56, 509–515. Okazawa, A., Akamatsu, M., Ohoka, A., Nishiwaki, H., Cho, W.-J., Nakagawa, Y., et al., 1998. Prediction <strong>of</strong> the binding mode <strong>of</strong> imidacloprid <strong>and</strong> related compounds to housefly head acetylcholine receptors using three-dimensional QSAR analysis. Pestic. Sci. 54, 134–144. Olsen, E.R., Dively, G.P., Nelson, J.O., 2000. Baseline susceptibility to imidacloprid <strong>and</strong> cross-resistance
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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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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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234 6: The Spinosyns: Chemistry, Bi
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236 6: The Spinosyns: Chemistry, Bi
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238 6: The Spinosyns: Chemistry, Bi
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240 6: The Spinosyns: Chemistry, Bi
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242 6: The Spinosyns: Chemistry, Bi
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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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250 7: Bacillus thuringiensis: Mech
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252 7: Bacillus thuringiensis: Mech
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254 7: Bacillus thuringiensis: Mech
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256 7: Bacillus thuringiensis: Mech
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258 7: Bacillus thuringiensis: Mech
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260 7: Bacillus thuringiensis: Mech
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262 7: Bacillus thuringiensis: Mech
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264 7: Bacillus thuringiensis: Mech
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266 7: Bacillus thuringiensis: Mech
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268 7: Bacillus thuringiensis: Mech
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270 7: Bacillus thuringiensis: Mech
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272 7: Bacillus thuringiensis: Mech
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274 7: Bacillus thuringiensis: Mech
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276 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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288 8: Mosquitocidal B. sphaericus:
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290 8: Mosquitocidal B. sphaericus:
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292 8: Mosquitocidal B. sphaericus:
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294 8: Mosquitocidal B. sphaericus:
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Table 4 Characteristics of various
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298 8: Mosquitocidal B. sphaericus:
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300 8: Mosquitocidal B. sphaericus:
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302 8: Mosquitocidal B. sphaericus:
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304 8: Mosquitocidal B. sphaericus:
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306 8: Mosquitocidal B. sphaericus:
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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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316 9: Insecticidal Toxins from Pho
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318 9: Insecticidal Toxins from Pho
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320 9: Insecticidal Toxins from Pho
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322 9: Insecticidal Toxins from Pho
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324 9: Insecticidal Toxins from Pho
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326 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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334 10: Genetically Modified Baculo
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366 10: Genetically Modified Baculo
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368 10: Genetically Modified Baculo
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370 10: Genetically Modified Baculo
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372 10: Genetically Modified Baculo
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374 10: Genetically Modified Baculo
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376 10: Genetically Modified Baculo
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378 10: Genetically Modified Baculo
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380 10: Genetically Modified Baculo
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382 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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390 11: Entomopathogenic Fungi and
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392 11: Entomopathogenic Fungi and
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394 11: Entomopathogenic Fungi and
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396 11: Entomopathogenic Fungi and
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398 11: Entomopathogenic Fungi and
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400 11: Entomopathogenic Fungi and
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402 11: Entomopathogenic Fungi and
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404 11: Entomopathogenic Fungi and
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406 11: Entomopathogenic Fungi and
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408 11: Entomopathogenic Fungi and
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410 11: Entomopathogenic Fungi and
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412 11: Entomopathogenic Fungi and
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414 11: Entomopathogenic Fungi and
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416 11: Entomopathogenic Fungi and
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418 11: Entomopathogenic Fungi and
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420 11: Entomopathogenic Fungi and
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422 11: Entomopathogenic Fungi and
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424 11: Entomopathogenic Fungi and
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426 11: Entomopathogenic Fungi and
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428 11: Entomopathogenic Fungi and
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430 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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442 12: Insect Transformation for U
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444 12: Insect Transformation for U
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446 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