Insect Control: Biological and Synthetic Agents - Index of

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esistance management programs due to their novel and different modes of action. The bisacylhydrazine insecticides are particularly attractive, due to their selective insect toxicity and high degree of mammalian and ecotoxicological reduced risk profiles. Acknowledgments The authors would like to thank Natalie Filion, CFS, Ontario, Canada, and Karan Dhadialla, University of Chicago, IL, USA, for sorting and typing the references in the required format. TSD also expresses his deep appreciation to Dow Agrociences LLC., Indianapolis, IN, USA (especially Drs. W. Kleshick and S. Evans) for support and encouragement in undertaking this writing. Part of the research was supported by grants from Gerome Canada and the Canadian Forest Service to AR and colleagues. GS also acknowledges the Fund for Scientific Research Flanders (FWO, Brussels, Belgium). References Adcock, G.J., Batterham, P., Kelly, L.E., McKenzie, J.A., 1993. Cyromazine resistance in Drosophila melanogaster (Diptera, Drosophilidae) generated by ethyl methanesulfonate mutagenesis. J. Econ. Entomol. 86, 1001–1008. Aliniazee, M.T., Arshad, M., 1998. Susceptibility of immature stages of the obliqued banded leafroller, Choristoneura rosaceana (Lepidoptera: Tortricidae) to fenoxycarb. J. Entomol. Soc. Br. Columbia 95, 59–63. Allgood, V.E., Eastman, E.M., 1997. Chimeric receptors as gene switches. Curr. Opin. Biotechnol. 8, 474–479. Aller, H.E., Ramsay, J.R., 1988. RH-5849 – A novel insect growth regulator with a new mode of action. Brighton Crop Prot. Conf. 2, 511–518. Anderson, M., Fisher, J.P., Robinson, J., Debray, P.H., 1986. Flufenoxuron – an acylurea acaricide/insecticide with novel properties. Brighton Crop Prot. Conf. 1, 89–96. Arbeitman, M.N., Hogness, D.S., 2000. Molecular chaperones activate the Drosophila ecdysone receptor, an RXR heterodimer. Cell 101, 67–77. Asano, S., Kuwano, E., Eto, M., 1986. Precocious metamorphosis induced by an anti-juvenile hormone compound applied to 3rd instar silkworm larvae, Bombyx mori L. (Leopidoptera: Bombycidae). App. Entomol. Zool. 21(2), 305–312. Ashburner, M., 1973. Sequential gene activation by ecdysone in polytene chromosomes of Drosophila melangaster. I. Dependence upon ecdysone concentration. Devel. Biol. 35, 47–61. Ashburner, M., Chiara, C., Meltzer, P., Richards, G., 1974. Temporal control of puffing activity in polytene chromosomes. Cold Spring Harbor Symp. Quant. Biol. 38, 655–662. 4: Insect Growth- and Development-Disrupting Insecticides 167 Ashok, M., Turner, C., Wilson, T.G., 1998. Insect juvenile hormone resistance gene homology with the bHLH- PAS family of transcriptional regulators. Proc. Natl Acad. Sci. USA 95(6), 2761–2766. Awad, T.I., Mulla, M.S., 1984. Morphogenetic and histopathological effects induced by the insect growth regulator cyromazine in Musca domestica (Diptera, Muscidae). J. Med. Entomol. 21, 419–426. Ayoade, O., Morooka, S., Tojo, S., 1995. Induction of macroptery, precocious metamorphosis, and retarded ovarian growth by topical application of precocene II, with evidence for its non-systemic allaticidal effects in the brown planthopper, Nilaparvata lugens. J. Insect Physiol. 42(6), 529–540. Balcells, M., Avilla, J., Profitos, J., Canela, R., 2000. Synthesis of phenoxyphenyl pyridine and pyrazine carboxamides activity against Cydia pomonella (L.) eggs. J. Agric. Food Chem. 48, 83–87. Banks, W.A., Lofgren, C.S., 1991. Effectiveness of the insect growth regulator pyriproxyfen against the red imported fire ant Hymenoptera formicidae. J. Entomol. Sci. 26(3), 331–338. Becher, H.M., Becker, P., Prokic-Immel, R., Wirtz, W., 1983. CME, a new chitin synthesis inhibiting insecticide. Brighton Crop Prot. Conf. 1, 408–415. Beckage, N.E., Riddiford, L.M., 1981. Effects of methoprene and juvenile hormone on larval ecdysis, emergence, and metamorphosis of the endoparasitic wasp, Apanteles Congregatus. J. Insect Physiol. 28(4), 329–334. Beckage, N.E., Riddiford, L.M., 1983. Lepidopteran antijuvenile hormones: effects on development of Apanteles congregatus in Manduca sexta. J. Insect Physiol. 29(8), 633–637. Bélai, I., Matolcsy, G., Farnsworth, D.E., Feyereisen, R., 1988. Inhibition of insect cytochrome P-450 by some metyrapone analogues and compounds containing a cyclopropylamine moiety and their evaluation as inhibitors of juvenile hormone biosynthesis. Pestic. Sci. 24, 205–219. Bellés, X., Baldellou, M.I., 1983. Precocious metamorphosis induced by precocenes on Oxycarenus lavaterae. Entomol. Exp. Appl. 34(2), 129–133. Bellés, X., Messegues, A., Piulachs, M.B., 1985. Sterilization induced by precocenes on females of Blatella gexmanica(L): short and long term effects. Zeitschrift fur Angewandte Entomologie 100, 409–417. Biddington, K.C., 1985. Ultrastructural changes in the cuticle of the sheep blowfly, Lucilia cuprina, induced by certain insecticides and biological inhibitors. Tissue Cell 17, 131–140. Billas, I.M.L., Moulinier, L., Rochel, N., Moras, D., 2001. Crystal structure of the ligand-binding domain of the ultraspiracle protein USP, the ortholog of retinoid X receptors in insects. J. Biol. Chem. 276, 7465–7474. Billas, I.M.L., Twema, T., Garnier, J.-M., Mitschler, A., Rochel, N., et al., 2003. Structural adaptability in the ligand-binding pocket of the ecdysone receptor. Nature 426, 91–96.
168 4: Insect Growth- and Development-Disrupting Insecticides Binder, B.F., Bowers, W.S., 1991. Behavioral changes and growth inhibition in last instar larvae of Heliothis zea induced by oral and topical application of precocene II. Entomol. Exp. Appl. 59, 207–217. Blackford, M., Dinan, L., 1997. The tomato moth Lacnobia oleracea (Lepidoptera: Noctuidae) detoxifies ingested 20-hydroxyecdysone, but is susceptible to the ecdysteroid agonists RH-5849 and RH-5992. Insect Biochem. Mol. Biol. 27, 167–177. Boivin, T., Chabert d’Hieres, C., Bouvier, J.C., Beslay, D., Sauphanor, B., 2001. Pleiotropy of insecticide resistance in the codling moth, Cydia pomonella. Entomol. Exp. Appl. 99, 381–386. Bonning, B.C., Hoover, K., Booth, T.F., Duffey, S., Hammock, B.D., 1995. Development of a recombinant baculovirus expressing a modified juvenile hormone esterase with potential for insect control. Arch. Insect Biochem. Physiol. 30, 177–194. Bourne, P.C., Whiting, P., Dhadialla, T.S., Hormann, R.E., Girault, J.-P., et al., 2002. Ecdysteroid 7,9(11)-dien-6ones as potential photoaffinity labels for ecdysteroid binding proteins. J. Insect Sci. 2, 1–11 (available online at http://www. insectscience.org/2.11). Bouvier, J.C., Boivin, T., Beslay, D., Sauphanor, B., 2002. Age-dependent response to insecticides and enzymatic variation in susceptible and resistant codling moth larvae. Arch. Insect Biochem. Physiol. 51, 55–66. Bowers, W.S., 1968. Juvenile hormone: activity of natural and synthetic synergists. Science 161, 895–897. Bowers, W.S., Nishida, R., 1980. Juvocimences L potent juvenile hormone mimics from sweet basil. Science 209, 1030–1032. Bowers, W.S., Unnithan, G.C., Fukushima, J., Toda, J., Sugiyama, T., 1995. Synthesis and biological activity of furanyl anti-juvenile hormone compounds. Pestic. Sci. 43, 1–11. Brindle, P.A., Baker, F.C., Tsai, L.W., Reuter, C.C., Schooley, D.A., 1987. Sources of proprionate for the biogenesis of ethyl-branched insect juvenile hormones: role of isoleucine and valine. Proc. Natl Acad. Sci. USA 84, 7906–7910. Bull, M.S., Swindale, S., Overend, D., Hess, E.A., 1996. Suppression of Boophilus microplus populations with fluazuron – an acarine growth regulator. Austral. Vet. J. 74, 468–470. Butenandt, A., Karlson, P., 1954. Uber die isolierung eines metamorphose-hormons des insekten in kristallisierter from Z. Naturforsch. Teil B 9, 389–391. Butler, L., Kondo, V., Blue, D., 1997. Effects of tebufenozide (RH-5992) for gypsy-moth (Lepidoptera, Lymantriidae) suppression on nontarget canopy arthropods. Env. Entomol. 26(5), 1009–1015. Cadogan, B.L., Retnakaran, A., Meating, J.H., 1997. Efficacy of RH5992, a new insect growth regulator against spruce budworm (Lepidoptera: Tortricidae) in a boreal forest. J. Econ. Entomol. 90, 551–559. Cadogan, B.L., Thompson, D., Retnakaran, A., Scharbach, R.D., Robinson, A., et al., 1998. Deposition of aerially applied tebufenozide (RH5992) on balsam fir (Abies balsamea) and its control of spruce budworm (Choristoneura fumiferana [Clem.]). Pestic. Sci. 53, 80–90. Cadogan, B.L., Scharbach, R.D., Krause, R.E., Knowles, K.R., 2002. Evaluation of tebufenozide carry-over and residual effects on spruce budworm (Lepidoptera: Tortricidae). J. Econ. Entomol. 95, 578–586. Campero, D.M., Haynes, K.F., 1990. Effects of methoprene on chemical communication, courtship, and oviposition in the cabbage looper (Lepidoptera: Noctuidae). J. Econ. Entomol. 83(6), 2263–2268. Cao, S., Qian, X., Song, G., 2001. N 0 -tert-butyl-N 0 -aroyl- N-(alkoxycarbonylmethyl)-N-aroylhydrazines, a novel nonsteroidal ecdysone agonist: synthesis, insecticidal activity, conformational, and crystal structure analysis. Can. J. Chem. 79, 272–278. Capinera, J.L., Epsky, N.D., Turick, L.L., 1991. Responses of Malonoplus sanguinipes and M. differentialis (Orthoptera: Acrididae) to fenoxycarb. J. Econ. Entomol. 84(4), 1163–1168. Carlson, G.R., Dhadialla, T.S., Hunter, R., Jansson, R.K., Jany, C.S., et al., 2001. The chemical and biological properties of methoxyfenozide, a new insecticidal ecdysteroid agonist. Pest Mgt. Sci. 57, 115–119. Carton, B., Heirman, A., Smagghe, G., Tirry, L., 2000. Relationship between toxicity, kinetics and in vitro binding of nonsteroidal ecdysone agonists in the cotton leafworm and the Colorado potato beetle. Med. Fac. Landbouww. Univ. Gent. 65(2a), 311–322. Celestial, D.M., McKenney, C.L.Jr., 1993. The influence of an insect growth regulator on the larval development of the mud crab Rhithropanopeus harrisii. Environ. Pollut. 85(2), 169–173. Chan, T.H., Ali, A., Britten, J.F., Thomas, A.W., Strunz, G.M., et al., 1990. The crystal structure of 1,2dibenzoyl-1-tert-butylhydrazine, a non-steroidal ecdysone agonist, and its effects on spruce bud worm (Choristoneura fumiferana). Can. J. Chem. 68, 1178–1181. Chandler, L.D., Pair, S.D., Harrison, W.E., 1992. RH- 5992, a new insect growth regulator active against corn earworm and fall armyworm (Lepidoptera: Noctuidae). J. Econ. Entomol. 85, 1099–1103. Chandler, L.D., 1994. Comparative effects of insect growth regulators on longevity and mortality of beet armyworm (Lepidoptera: Noctuidae) larvae. J. Entomol. Sci. 29, 357–366. Charles, J.P., Wojtasek, H., Lentz, A.J., Thomas, B.A., Bonning, B.C., et al., 1996. Purification and reassessment of ligand binding by the recombinant, putative juvenile hormone receptor of the tobacco hornworm, Manduca sexta. Arch. Insect. Biochem. Physiol. 31, 371–393. Cherbas, P., Cherbas, L., Lee, S.-S., Nakanishi, K., 1988. [1251]iodo-ponasterone A is a potent ecdysone and a sensitive radioligand for ecdysone receptors. Proc. Natl Acad. Sci., USA 85, 2096–2100. Chen, N.M., Borden, J.H., 1989. Adverse effect of fenoxycarb on reproduction by the california fivespined IPS,
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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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Studies were also done using compar
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Becke, 1988; Klamt, 1995) level of
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sampling using forcefield methods (
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Figure 9 Stable conformations and p
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Figure 13 Binding to putative catio
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Figure 14 Systemicity of neonicotin
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site (Kayser et al., 2002). Clothia
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Figure 20 Important pest insects ta
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Barley yellow dwarf virus vectors s
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investigate the mode of action of n
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within the desensitized state over
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the accumulation of this acid in th
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3.8.1. Safety Profile The introduct
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Table 7 Environmental profile of co
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substance is bound irreversibly to
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imidacloprid conferring a high leve
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nAChR are comparable to the efficac
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Figure 25 Flea control achieved wit
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and the resolution of FAD was teste
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Brown, J.K., Perring, T.M., Cooper,
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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.
Page 128 and 129: for control of stinkbugs in soybean
Page 130 and 131: Biochem. Physiol., doi: 10.1016/j.p
Page 132 and 133: 4 Insect Growth- and Development-Di
Page 134 and 135: The molting process is initiated by
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
Page 144 and 145: thus inducing effects and symptomol
Page 146 and 147: and microsomes. Subsequently, Willi
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
Page 156 and 157: their reduced risk for the environm
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
Page 170 and 171: Flucycloxuron Nonsystemic acaricide
Page 172 and 173: The discovery of diflubenzuron spaw
Page 174 and 175: Table 15 Environmental effects of s
Page 176 and 177: ecessive (R male S female) manner,
Page 180 and 181: IPS Paraconfusus lanier (Coleoptera
Page 182 and 183: larvae parasitized by Microplitis r
Page 184 and 185: Kostyukovsky, M., Chen, B., Atsmi,
Page 186 and 187: Three-dimensional quantitative stru
Page 188 and 189: Riddiford, L.M., 1994. Cellular and
Page 190 and 191: characterization of resistant clone
Page 192 and 193: Biological Approaches to Pest Contr
Page 194 and 195: M389 L308 M272 T304 T393 V404 L420
Page 196 and 197: 5 Azadirachtin, a Natural Product i
Page 198 and 199: and Hemiptera and was related to ef
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Page 202 and 203: important source of pest control at
Page 204 and 205: effects with physiological effects
Page 206 and 207: eing associated with an accumulatio
Page 208 and 209: et al., 1992). Salehzadeh et al. (2
Page 210 and 211: ehavior of Spodoptera littoralis (p
Page 212 and 213: indica A. Juss. IBH Publishing Comp
Page 214 and 215: Smith, S.L., Mitchell, M.J., 1988.
Page 216 and 217: which interact directly with azadir
Page 218 and 219: 6 The Spinosyns: Chemistry, Biochem
Page 220 and 221: Table 1 Structures of the spinosyns
Page 222 and 223: Table 2 Biological activity of spin
Page 224: A large synthetic effort has gone i
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Figure 4 Spinosad metabolism in avi
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220 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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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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