Insect Control: Biological and Synthetic Agents - Index of

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Smith, S.L., Mitchell, M.J., 1988. Effects of azadirachtin on insect cytochrome-P450 dependent ecdysone 20monooxygenase activity. Biochem. Biophys. Res. Comm. 154, 559–563. Stark, J.D., Vargas, R.I., Thalman, R.K., 1990. Azadirachtin: effects on metamorphosis, longevity, and reproduction of three tephritid fruit-fly species (Diptera, Tephritidae). J. Econ. Entomol. 83, 2168–2174. Stark, J.D., Walter, J.F., 1995. Persistence of azadirachtin A and azadirachtin B in soil: effects of temperature and microbial activity. J. Environ. Sci. Health B 30, 685–698. Su, T.Y., Mulla, M.S., 1998. Antifeedancy of neem products containing azadirachtin against Culex tarsalis and Culex quinquefasciatus (Diptera: Culicidae). J. Vector Ecol. 23, 114–122. Su, T.Y., Mulla, M.S., 1999. Effects of neem products containing azadirachtin on blood feeding, fecundity, and survivorship of Culex tarsalis and Culex quinquefasciatus (Diptera: Culicidae). J. Vector Ecol. 24, 202–215. Subrahmanyam, B., Müller, T., Rembold, H., 1989. Inhibition of turnover of neurosecretion by azadirachtin in Locusta migratoria. J. Insect Physiol. 35, 493–497. Sundaram, K.M.S., 1996. Azadirachtin biopesticide: a review of studies conducted on its analytical chemistry, environmental behaviour and biological effects. J. Environ. Sci. Health B 31, 913–948. Sundaram, K.M.S., Campbell, R., Sloane, L., Studens, J., 1995. Uptake, translocation, persistence and fate of azadirachtin in aspen plants (Populus tremuloides Michx) and its effect on pestiferous two-spotted spider-mite (Tetranychus urticae Koch). Crop Protect. 14, 415–421. Sundaram, K.M.S., Sundaram, A., Curry, J., Sloane, L., 1997. Formulation selection, and investigation of azadirachtin-A persistence in some terrestrial and aquatic components of a forest environment. Pest. Sci. 51, 74–90. Tang, D.L., Wang, C.Z., Luo, L., Qin, J.D., 2000. Comparative study on the responses of maxillary sensilla 5: Azadirachtin, a Natural Product in Insect Control 203 styloconica of cotton bollworm Helicoverpa armigera and oriental tobacco budworm H. assulta larvae to phytochemicals. Sci. China Series C Life Sci. 43, 606–612. Tang, Y.Q., Weathersbee, A.A., Mayer, R.T., 2002. Effect of neem seed extract on the brown citrus aphid (Homoptera: Aphididae) and its parasitoid Lysiphlebus testaceipes (Hymenoptera: Aphidiidae). Environ. Entomol. 31, 172–176. Tanzubil, P.B., McCaffery, A.R., 1990. Effects of azadirachtin and aqueous neem seed extracts on survival, growth and development of the African armyworm, Spodoptera exempta. Crop Protect 9, 383–386. Timmins, W.A., Reynolds, S.E., 1992. Azadirachtin inhibits secretion of trypsin in midgut of Manduca sexta caterpillars: reduced growth due to impaired protein digestion. Entomol. Exp. Applic. 63, 47–54. Trisyono, A., Whalon, M.E., 1999. Toxicity of neem applied alone and in combinations with Bacillus thuringiensis to Colorado potato beetle (Coleoptera: Chrysomelidae). J. Econ. Entomol. 92, 1281–1288. Trumm, P., Dorn, A., 2000. Effects of azadirachtin on the regulation of midgut peristalsis by the stomatogastric nervous system in Locusta migratoria. Phytoparasitica 28, 7–26. Turner, C.J., Tempesta, M.S., Taylor, R.B., Zagorski, M.G., Termini, J.S., et al., 1987. An NMR spectroscopic study of azadirachtin and its trimethyl ether. Tetrahedron 43, 2789–2803. von Friesewinkel, D.C., Schmutterer, H., 1991. Kontaktwirkung von Niemol bei der afrikanischen Wanderheuschrecke Locusta migratoria migratorioides (R&F). Z. Angew. Zool. 78, 189–204. Weintraub, P.G., Horowitz, A.R., 1997. Systemic effects of neem insecticide on Lyriomyza huidobrensis larvae. Phytoparasitica 25, 283–289. Wong, W.L., Brostrom, M.A., Kuznetsov, G., Gmitter- Yellen, D., Brostrom, C.O., 1993. Inhibition of protein synthesis and early protein processing by thapsigargin in cultured cells. Biochem. J. 289, 71–79.
A5 Addendum: Azadirachtin, A Natural Product in Insect Control: An Update A J Mordue (Luntz), University of Aberdeen, Aberdeen, UK E D Morgan, Keele University, Keele, UK A J Nisbet, Moredun Research Institute, Edinburgh, UK ß 2010 Elsevier B.V. All Rights Reserved A5.1. Synthesis of Azadirachtin 204 A5.2. Emerging Technologies for Understanding Mode of Action 204 A5.3. Commercial Use of Neem Seed Insecticides 205 A5.4. Conclusions 205 A5.1. Synthesis of Azadirachtin A milestone in the chemistry of azadirachtin was reached in 2007. Forty one years after the isolation of azadirachtin and twenty one years after the full solution of its chemical structure, its synthesis was completed. This was by no means an indication that synthetic azadirachtin will be available in the future. It is the crowning glory of azadirachtin chemistry, and a remarkable feat for the art and science of synthetic organic chemistry (Jauch, 2008). Steven Ley and his group at Cambridge did it in 71 steps and the overall yield was 0.00015% (Veitch et al., 2007a). The synthesis was accomplished by a relay method (Veitch et al., 2007b). That is, azadirachtin was degraded to a simpler product A (Figure A1), which was then reconverted back to azadirachtin in the laboratory. Starting from a simple three-carbon compound, the ‘‘lefthand’’ decalin portion of the molecule was built up with an array of protecting groups that could be removed later. The ‘‘right-hand’’ portion was similarly constructed, starting from galactose. These two portions proved impossible to join by any known chemical method. A different ‘‘right-hand’’ molecule was constructed, and finally attached to the ‘‘lefthand’’ part, and in eight more steps the relay compound A was produced, completing the synthesis (Figure A1). The importance of azadirachtin chemically and biologically meant that several groups in other places were hard at work on the synthesis at the same time. The successful route enabled the Ley group to make five other compounds closely related to azadirachtin, all of which will be valuable on the way to understanding structure–activity relationships in this group. A5.2. Emerging Technologies for Understanding Mode of Action The mode of action of azadirachtin still requires resolution. A recent study showed azadirachtin promoted caspase-independent apoptosis in wing and eye imaginal discs when fed to larval Drosophila melanogaster and was associated with actin cytoskeletal depletion (Anuradha et al., 2007). These observations, accompanied by in silico modeling of azadirachtin binding to b actin suggest that azadirachtin exerts its effects via direct binding to cytoskeletal actin (Pravin Kumar et al., 2007). In vitro evidence from Drosophila cells suggests that azadirachtin binds directly to a protein complex, which contains a chaperone protein, HSP 60 (Robertson et al., 2007). Other studies point to tubulin polymerization as the biological target of the mode of action (reviewed in Mordue (Luntz) et al., 2005). From these studies it has therefore been impossible to attach a single unequivocal biochemical target for azadirachtin in insect cells and this may indeed point to promiscuity in regard to the biochemical target(s) of the molecule. Current knowledge from these in vivo, in vitro and in silico models needs to be refined using a ‘‘systems biology approach’’ to clarify the mode of action. Using azadirachtin and the new analogues (see above) in a genetically-tractable model species should lead to a deeper understanding of its mode of action at the molecular level. Compound-centric chemical proteomics (reviewed by Rix and Superti- Furga, 2009) – a postgenomic variant on the classical drug-affinity studies previously performed with azadirachtin – will allow identification of proteins
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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.
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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
Page 164 and 165: Table 9 Continued Bemisia tabaci (s
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Page 192 and 193: Biological Approaches to Pest Contr
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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
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254 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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