Insect Control: Biological and Synthetic Agents - Index of

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observed resistance to pyrethroids, with a kdr mechanism being the main contributor. This case further emphasized the need for not only accurately identifying the resistance mechanisms present but also their relative contribution. One way forward would be to design selective inhibitors on the basis of in vivo and in vitro structure–activity relationship studies from susceptible and resistant insects. 1.5.2.1. Chemistry-led options for circumventing resistance The established IRM strategies (considered above) successfully exploit a range of options including use of insecticides with different modes of action, agronomic practices, and biological control. However, there are two additional options involving insecticides that have hitherto not been fully exploited. 1. Negative cross-resistance is a phenomenon in which a resistant pest is rendered more susceptible to another class of pesticide. This phenomenon is rare in insects but for pyrethroids, two different classes, the N-alkylamides (Elliott et al., 1986) and dihydropyrazoles (and related classes) (Khambay et al., 2001), have been found to cause this effect. They both exhibit similar, albeit small (resistance factors of 0.4), levels of negative cross-resistance to houseflies with nerve insensivity (super-kdr) as the main resistance mechanism. The mechanisms involved are not properly understood. However this phenomenon is apparent only in the presence of the super-kdr mechanism, with kdr alone having little impact. BTG 502 (Figure 8; (58)) is representative of the N-alkylamides, a class with which this phenomenon was first identified. No compounds of this class have been commercialized to date, but see Chapter 2. In insects that have developed resistance to pyrethroids as a consequence of increased levels of metabolic enzymes (MFOs and esterases), negative cross-resistance has been demonstrated Figure 8 Compounds referred to in the resistance section (structures 58–61). 1: Pyrethroids 23 towards insecticides that require in vivo activation (i.e., pro-insecticides). For example, negative cross-resistance has been observed with indoxacarb in H. armigera with increased levels of esterases (Gunning, 2003). However, this compound has little effect in M. persicae with elevated levels of esterase (Khambay, unpublished data). This difference may be accounted for by the kinetics of the hydrolysis reaction. In susceptible H. armigera, hydrolysis is incomplete by the end of the bioassay time. The increased levels of esterases in resistant H. armigera generate more active compound over the same period, resulting in a higher level of activity. In M. persicae, the hydrolysis is complete during the test period even in susceptible insects and therefore no additional effects are observed if increased levels of esterases are present. Negative cross-resistance has also been observed for pyrethroid-resistant insects with increased levels of MFOs. Examples of such insecticides include the pyrazole chlofenapyr, the organophorothioates diazinon and chlorpyrifos, and the methylcarbamate propoxur. 2. Pyrethroids constitute a diverse class of chemical structures and levels of resistance to them also vary considerably. For example, in houseflies with the super-kdr resistance mechanism, the resistance factor for different pyrethroids can vary from less than 10 to over 500. Structure– activity relationships have been discerned and the levels of resistance factors (RFs, derived by dividing the LD50 of resistant insects by that of the corresponding susceptible insects) have been shown to be directly influenced by the nature of the alcohol group and the a substituent, but independent of the nature of the acid group (Farnham and Khambay, 1995a, 1995b; Beddie et al., 1996). This is reflected in the description of Types I and II. Thus, highest RFs are shown by compounds with a 3-phenoxybenzyl (or
24 1: Pyrethroids equivalent) alcohol ester with an a-cyano substituent (e.g., deltamethrin) with an RF of 560. The RF of 91 for NRDC 157 (59) (deltamethrin analog lacking the a-cyano group) is significantly smaller, and indeed surprisingly the LD 50 values against super-kdr flies are similar for the two compounds. This indicates that the additional target-site binding, and hence increased insecticidal activity, in susceptible flies gained by introducing an a-cyano group into NRDC 157 has been lost in super-kdr flies. The lowest RFs are observed for pyrethroids with alcohols containing a single ring and no a substituent, an example being tefluthrin with RF < 4. In H. armigera, there has been some controversy regarding the resistance mechanism. Though it is accepted that the major mechanism is due to increased metabolism, it is unclear whether MFOs or esterases prevail. The highest RFs were shown by ester pyrethroids containing a phenoxybenzyl alcohol moiety in combination with an aromatic acid. The lowest RFs were with pyrethroids containing simple alcohol moieties as in bioallethrin. Resistance-breaking pyrethroids (RF < 1) were also identified e.g., those containing a methylenedioxyphenyl moiety as in Scott’s Py III (60) and Cheminova 1 (61). This approach clearly has potential to prolong the usefulness of pyrethroids as a class of insecticides. However, the agrochemical industries are unlikely to develop new pyrethroids purely for a role in ‘‘breaking’’ resistance to established compounds due to commercial considerations. Despite the detection of resistance to pyrethroids soon after their introduction over 30 years ago, it has proved possible to manage it in many field situations. Therefore it is likely that pyrethroids will continue to be a useful tool for the foreseeable future. Acknowledgments We thank Dr Richard Bromilow for assistance in preparing this manuscript. Rothamsted Research receives grant-aided support from the Biotechnology and Biological Sciences Research Council, UK. References Abdelaal, Y.A.I., Soderlund, D.M., 1980. Pyrethroidhydrolyzing esterases in southern armyworm larvae – tissue distribution, kinetic properties, and selective inhibition. Pestici. Biochem. Physiol. 14, 282–289. AbdElghafar, S.F., Knowles, C.O., 1996. Pharmacokinetics of fenvalerate in laboratory and field strains of Helicoverpa zea (Lepidoptera: Noctuidae). J. Econ. Entomol. 89, 590–593. Ahmad, M., McCaffery, A.R., 1999. Penetration and metabolism of trans-cypermethrin in a susceptible and a pyrethroid-resistant strain of Helicoverpa armigera. Pestici. Biochem. Physiol. 65, 6–14. Akamatsu, M., 2002. Studies on three-dimensional quantitative structure–activity relationships in pesticides. J. Pestici. Sci. 27, 169–176. Anspaugh, D.D., Rose, R.L., Koehler, P.G., Hodgson, E., Roe, R.M., 1994. Multiple mechanisms of pyrethroid resistance in the German cockroach, Blattella germanica (L). Pestici. Biochem. Physiol. 50, 138–148. Beddie, D.G., Farnham, A.W., Khambay, B.P.S., 1996. The pyrethrins and related compounds. 41. Structureactivity relationships in non-ester pyrethroids against resistant strains of housefly (Musca domestica L). Pestici. Sci. 48, 175–178. Bigley, W.S., Plapp, F.W., 1978. Metabolism of cis- [C-14]-permethrin and trans-[C-14]-permethrin by tobacco budworm and bollworm. J. Agric. Food Chem. 26, 1128–1134. Bloomquist, J.R., Miller, T.A., 1985. Carbofuran triggers flight motor output in pyrethroid-blocked reflex pathways of the house-fly. Pestici. Biochem. Physiol. 23, 247–255. Briggs, G.G., Elliott, M., Farnham, A.W., Janes, N., Needham, P.H., et al., 1976. Insecticidal activity of the pyrethrins and related compounds VIII. Relationship of polarity with activity in pyrethroids. Pestici. Sci. 7, 236–240. Bryant, R., 1999. Agrochemicals in perspective: analysis of the worldwide demand for agrochemical active ingredients. The Fine Chemicals Conference 99 [synopsis on the Internet] http://agranova.co.uk/agtalk99.asp Accessed 23 April 2004. Busvine, J.R., 1951. Mechanism of resistance to insecticide in houseflies. Nature 168, 193–195. Byrne, F.J., Gorman, K.J., Cahill, M., Denholm, I., Devonshire, A.L., 2000. The role of B-type esterases in conferring insecticide resistance in the tobacco whitefly, Bemisia tabaci (Genn). Pest Manage. Sci. 56, 867–874. Casida, J.E., Ruzo, L.O., 1980. Metabolic chemistry of pyrethroid insecticides. Pestici. Sci. 11, 257–269. Cheung, K.W., Sirur, G.M., 2002. Agrochemical Products Database, 2002. Cropnosis Limited, Edinburgh, UK. Chuman, H., Goto, S., Karasawa, M., Sasaki, M., Nagashima, U., et al., 2000a. Three-dimensional structure–activity relationships of synthetic pyrethroids: 1. Similarity in bioactive conformations and their structure–activity pattern. Quant. Struct.-Activ. Relationships 19, 10–21. Chuman, H., Goto, S., Karasawa, M., Sasaki, M., Nagashima, U., et al., 2000b. Three-dimensional structure–activity relationships of synthetic pyrethroids: 2. Three-dimensional and classical QSAR studies. Quant. Struct.-Activ. Relationships 19, 455–466. Corbel, V., Chandre, F., Darriet, F., Lardeux, F., Hougard, J.M., 2003. Synergism between permethrin and
Page 2 and 3: INSECT CONTROL BIOLOGICAL AND SYNTH
Page 4 and 5: INSECT CONTROL BIOLOGICAL AND SYNTH
Page 6 and 7: CONTENTS Preface vii Contributors i
Page 8 and 9: PREFACE When Elsevier published the
Page 10 and 11: J T Andaloro E. I. Du Pont de Nemou
Page 12 and 13: 1 Pyrethroids B P S Khambay and P J
Page 14 and 15: activity. In contrast to most other
Page 16 and 17: Figure 1 Commercial and novel pyret
Page 18 and 19: 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 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 70 and 71: R1 N N O N H indoxacarb. Thus, whil
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 (
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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.
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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
Page 166 and 167:
Table 11 Insect control with some a
Page 168 and 169:
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
Page 176 and 177:
ecessive (R male S female) manner,
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esistance management programs due t
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IPS Paraconfusus lanier (Coleoptera
Page 182 and 183:
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
Page 481:
470 Subject Index Toxocara cati, im
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