Insect Control: Biological and Synthetic Agents - Index of

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Figure 1 Commercial and novel pyrethroids (structures 1–28). 1: Pyrethroids 5
6 1: Pyrethroids Table 1 Insecticidal and mammalian toxicity of pyrethrin I and selected pyrethroids Pyrethroid Representative median lethal dose (mg kg 1 ) Housefly, Musca domestica Rat, oral Pyrethrin I (1) 30 420 Bioresmethrin (3) 6 800 Permethrin (4) 0.7 2000 Deltamethrin (6) 0.02 100 Table 2 Isomer mixtures of pyrethroids Pyrethroid Product Number of isomers Stereochemistry Cypermethrin 8 (1R )-cis, aS; (1S )-cis, aR (1R )-cis, aR; (1S )-cis, aS (1R )-trans, aS; (1S )-trans, aR (1R )-trans, aR; (1S )-trans, aS Alpha 2 (1R )-cis, aS; (1S )-cis, aR Beta 4 (1R )-cis, aS; (1S )-cis, aR (1R )-trans, aS; (1S )-trans, aR Theta 2 (1R )-trans, aS; (1S )-trans, aR Zeta 4 (1R )-cis, aS; (1S )-cis, aS (1R )-trans, aS; (1S )-trans, aS Cyhalothrin 4 (1R )-cis, aS; (1S )-cis, aR (1R )-trans, aS; (1S )-trans, aR Lambda 2 (1R )-cis, aS; (1S )-cis, aR Gamma 1 (1R )-cis, aS Fluvalinate 4 (2R), aR; (2R), aS (2S ), aS; (2S ), aS Tau 2 (2R ), aR; (2R ), aS eight isomers but is sold as a mixture of two active cis/trans isomers, each with the 1R center at C1 and aS in the alcohol moiety. 1.3. Structure–Activity Relationships in Pyrethroids As described above, pyrethroids form a diverse class of insecticides highly effective against a broad spectrum of insect and acarine pests. The level of activity is determined by penetration, metabolism within the insect, and the requirements at the target site. As an illustration (see Figure 2 for structures), pyrethrin I has good activity against houseflies but poor activity against mites, whereas an experimental compound (29) has very high miticidal but poor insecticidal activity. Despite this diversity, it is possible to make some generalizations regarding structural requirements for high activity in pyrethroids. The sevensegment model (Figure 3) based on pyrethrin I, the lead structure originally adopted by Elliott (Elliott and Janes, 1978), serves as a good model to illustrate these general requirements and exceptions to them. Segment A: Unsaturation generally leads to high activity. However, exceptions are known; for example fenpropathrin (41), containing the tetramethylcyclopropane acyl moiety (lacking in unsaturation), has high insecticidal and acaricidal activity. In general, large variations (steric and electronic) can be tolerated in this region. For example, (30) has an extended sidechain compared with cypermethrin and yet their activity is similar; flumethrin (8), possessing a bulky aromatic substituent, is highly active towards ticks. Segment A þ B: In ester pyrethroids, the gemdimethyl group or its steric equivalent must be beta to the ester group. The required geometrical stereochemistry (cis/trans) across the cyclopropane ring (segment B) is influenced by the nature of the alcohol moiety, substituent at C3 and test species. In general, IR-trans-chrysanthemates (as in bioresmethrin) are more active then the corresponding cis isomers. The vinyl dihalo substituents are generally more effective than the chrysanthemates; however, the relative activity of the cis and trans isomers varies considerably. For alcohols containing two rings (e.g., 3-phenoxybenzyl alcohol as in deltamethrin), the 1R-cis isomers are generally more active than the trans isomers, but with alcohol moieties that contain a single ring (e.g., pentafluorobenzyl as in fenfluthrin (31) and cyclopentenone as in allethrin) the converse is true, with the trans isomers being more active. In pyrethrin II, the vinyl carbomethoxy group in the acid moiety has the E configuration. Its corresponding analogs, cis and trans esters of a-cyano- 3-phenoxybenzyl alcohol, are equally active; the Z isomer of the nor homolog (e.g., (32)) of the cis (but not the trans) isomer was unexpectedly much more active. Acrinathrin incorporates these two features and, although only half as active as deltamethrin against houseflies, it is more active towards some species of mites, ticks, lepidopteran insects, and sucking pests. Furthermore, stereochemistry also influences species selectivity of pyrethroids, a process primarily determined by selective metabolism. For example, contrary to the above generalization for pyrethroids containing 3-phenoxybenzyl
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 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 34 and 35: observed resistance to pyrethroids,
Page 36 and 37: propoxur against Culex quinquefasci
Page 38 and 39: esistance in house fly. Insect Bioc
Page 40 and 41: Shan, G.M., Hammock, B.D., 2001. De
Page 42 and 43: A1.4. Resistance The increasing num
Page 44 and 45: B A IIS4-S5 linker, IIS5 helix and
Page 46 and 47: 2 Indoxacarb and the Sodium Channel
Page 48 and 49: Figure 2 Structures of pyrazoline-l
Page 50 and 51: observed that both indoxacarb and i
Page 52 and 53: deflections resulting from stresses
Page 54 and 55: Figure 8 Dihydropyrazole block appe
Page 56 and 57: potential conduction in the CNS of
Page 58 and 59: known to affect blocker affinity, w
Page 60 and 61: Figure 13 Diagrammatic representati
Page 62 and 63: that the probable mechanism of ovil
Page 64 and 65: conventional chemistries and spinos
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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.
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for control of stinkbugs in soybean
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Biochem. Physiol., doi: 10.1016/j.p
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4 Insect Growth- and Development-Di
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The molting process is initiated by
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Table 1 Bisacylhydrazine insecticid
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4.2.2. Bisacylhydrazines as Tools o
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to the three EcRs with either muris
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of action of ecdysone agonists was
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thus inducing effects and symptomol
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and microsomes. Subsequently, Willi
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dipteran insects, like the midge, C
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eetle (Exomala orientalis) when app
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metabolic fate studies showed the i
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y specific proteins in signaling pa
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their reduced risk for the environm
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can be reversed by applying JH. JH
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door for a more rational approach t
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apparent that it was a bHLH-PAS and
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Table 9 Continued Bemisia tabaci (s
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Table 11 Insect control with some a
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Table 13 Ecotoxicological profile o
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Flucycloxuron Nonsystemic acaricide
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The discovery of diflubenzuron spaw
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Table 15 Environmental effects of s
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ecessive (R male S female) manner,
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esistance management programs due t
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IPS Paraconfusus lanier (Coleoptera
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larvae parasitized by Microplitis r
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Kostyukovsky, M., Chen, B., Atsmi,
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Three-dimensional quantitative stru
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Riddiford, L.M., 1994. Cellular and
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characterization of resistant clone
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Biological Approaches to Pest Contr
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M389 L308 M272 T304 T393 V404 L420
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5 Azadirachtin, a Natural Product i
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and Hemiptera and was related to ef
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eported, but this is rather nonspec
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important source of pest control at
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effects with physiological effects
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eing associated with an accumulatio
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et al., 1992). Salehzadeh et al. (2
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ehavior of Spodoptera littoralis (p
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indica A. Juss. IBH Publishing Comp
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Smith, S.L., Mitchell, M.J., 1988.
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which interact directly with azadir
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6 The Spinosyns: Chemistry, Biochem
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Table 1 Structures of the spinosyns
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Table 2 Biological activity of spin
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A large synthetic effort has gone i
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216 6: The Spinosyns: Chemistry, Bi
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Figure 4 Spinosad metabolism in avi
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A6 Addendum: The Spinosyns T C Spar
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246 A6: Addendum Scott, 2008) and i
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248 7: Bacillus thuringiensis: Mech
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A7 Addendum: Bacillus thuringiensis
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280 A7: Addendum toxins is magnitud
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Table 1 Comparative properties of s
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286 8: Mosquitocidal B. sphaericus:
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Table 4 Characteristics of various
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A8 Addendum: Bacillus sphaericus Ta
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310 A8: Addendum essential to devel
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314 9: Insecticidal Toxins from Pho
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A9 Addendum: Recent Advances in Pho
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330 A9: Addendum Lee, S.C., Stoilov
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332 10: Genetically Modified Baculo
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384 A10: Addendum cysteine protease
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388 11: Entomopathogenic Fungi and
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Zare, R., Gams, W., Culham, A., 200
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434 A11: Addendum although a number
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436 A11: Addendum Examination of ge
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440 12: Insect Transformation for U
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448 A12: Addendum genetic transform
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452 Subject Index Aphis gossypii (c
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454 Subject Index Bisacylhydrazine
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456 Subject Index Cry toxins (conti
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458 Subject Index Entomopathogenic
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460 Subject Index Homoptera molting
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462 Subject Index Kinoprene (ENSTAR
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464 Subject Index Muscle(s) sodium
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466 Subject Index Photorhabdus (con
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468 Subject Index Sodium channel bl
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470 Subject Index Toxocara cati, im
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