Insect Control: Biological and Synthetic Agents - Index of

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very large, unusual, complex molecules, and metabolic enzyme systems do exhibit distinct substrate specificities. Studies of spinosyn A metabolism in tobacco budworm (H. virescens) larvae show spinosyn A to penetrate slowly, and that the primary, and apparently only, component that was detected (within the limits of the experiment) was the parent, spinosyn A (Sparks et al., 1997, 2001) (Figure 5). Thus, until 24 h post treatment there appears to be little or no metabolism of spinosyn A in pest insects such as larvae of H. virescens. In contrast, these same larvae readily metabolize the quinazoline acaricide, fenazaquin (Sparks et al., 1997) (Figure 5). Subsequent studies with H. virescens larvae that were highly resistant (ca. 1000-fold) (Bailey et al., 1999) to spinosad, also failed to show significant levels of metabolism (Young et al., 2000). These observations are in clear distinction to those observed for mammals (see Section 6.3.1.1). The apparent lack of spinosyn A metabolism by pest insects is also supported by synergist studies with the monooxygenase inhibitor, piperonyl butoxide (PBO). PBO is able to synergize the biological activity of the pyrethroid permethrin in house flies, but not that of spinosyn A (Sparks et al., 1997). Likewise no PBO-based synergism was noted for spinosyn A or spinosad activity in studies involving H. virescens larvae (Sparks et al., 1997) or in spinosad resistant larvae of the diamondback moth (Plutella xylostella) (Zhao et al., 2002). Thus, within the limits of the available data, many pest insects appear to have a limited capacity to metabolize some spinosyns. 6.3.2. Spinosyn Penetration into Insects 6: The Spinosyns: Chemistry, Biochemistry, Mode of Action, and Resistance 215 The observed biological activity of any toxicant is a function of two primary parameters: (1) inherent activity at the target site, and (2) concentration of the toxicant at the target site as a function of time. Compared to more conventional insect control agents such as the organophosphates, carbamates, and pyrethroids, the spinosyns are large, complex, relatively high molecular weight molecules. Although the spinosyns, such as spinosyn A, exhibit good activity via topical or contact application, better activity is observed by oral application or by injection (Sparks et al., 1995, 1997, 1998), suggesting that penetration through the insect cuticle may be comparatively slow. In contrast, insecticides such as cypermethrin are equitoxic to lepidopterous larvae by either topical application or injection (Sparks et al., 1997), suggesting relatively rapid penetration through the cuticle of pest insect larvae. A time course of penetration of permethrin or spinosyn A into the hemolymph of larvae of the cabbage looper (Trichoplusia ni) (Sparks et al., 1997) showed the rate of penetration for spinosyn A to be much slower than that of the pyrethroid permethrin. Likewise, studies of initial penetration rates (2–4 h) for a variety of insect control agents showed that spinosyn A possessed one of the slowest rates of penetration. Most organophosphate and pyrethroid insect control agents have initial rates of penetration that are several-fold higher; in some cases by more than an order of magnitude (Table 5). Interestingly, one compound that is reported to have a similarly slow rate of penetration is abamectin, another large macrolide (Table 5). Thus, in light of the very good biological activity possessed by many of the spinosyns, their comparatively slow rate of penetration may be well compensated for by a limited capacity of many pest insects to metabolize them. 6.3.3. Insecticidal Concentration in the Cockroach A key parameter in understanding the mode of action of biologically active compounds is the aqueous concentration that needs to be in contact with the receptors in the body to cause the biological effect of interest. For pharmaceuticals, the therapeutic concentration is defined as the aqueous concentration of the substance in the patient’s blood plasma needed to obtain a desired therapeutic effect. Likewise, the insecticidal concentration can be defined as the concentration of an insecticide in the aqueous phase of an insect’s hemolymph needed to obtain a desired insecticidal effect. Hemolymph is a complex tissue, composed of cells suspended in a complex solution of salts and organic molecules, including high concentrations of proteins. Whole hemolymph concentration, as is usually measured for insecticides, is in itself not interesting for the mode of Figure 3 Potential biosynthesis of spinosyn A. PSA, pseudoaglycone. (Adapted, in part, from information in Kirst, H.A., Michel, K.H., Mynderse, J.S., Chio, E.H., Yao, R.C., et al., 1992. Discovery, isolation, and structure elucidation of a family of structurally unique fermentation-derived tetracyclic macrolides. In: Baker, D.R., Fenyes, J.G., Steffens, J.J. (Eds.), Synthesis and Chemistry of Agrochemicals, vol. 3. American Chemical Society, Washington, DC, pp. 214–225; Waldron, C., Madduri, K., Crawford, K., Merlo, D.J., Treadway, P., et al., 2000. A cluster of genes for the biosynthesis of spinosyns, novel macrolide insect control agents produced by Saccharopolyspora spinosa. Antonie van Leeuwenhoek 78, 385–390; and Waldron, C., Matsushima, P., Rosteck, P.R., Jr., Broughton, M.C., Turner, J., et al., 2001. Cloning and analysis of the spinosad biosynthetic gene cluster of Saccharopolyspora spinosa. Chem. Biol. 8, 487–499.)
216 6: The Spinosyns: Chemistry, Biochemistry, Mode of Action, and Resistance Table 3 Biological activity of novel spinosyns and spinosoids towards selected insect and mite species Number Compound Heliothis virescens, neonate (LC50, ppm) Stomoxys calcitrans, adult (LC50, ppm) Aphis gossypii (LC50, ppm) Macrosteles quadrilineatus (LC50, ppm) Novel spinosyns 30 21-Propyl A 0.16 27 31 21-Butenyl A 0.29 5.2 1.4 Tetranychus urticae (LC50, ppm) Spinosoids 32 N-demethyl D 5.6 >50 0.1 33 N-demethyl K 9.9 8.2 0.5 34 N,N-didemethyl K 7.4 11.1 3.4 35 2 0 -H A 0.23 0.24 134 36 2 0 -H D 0.23 25 37 2 0 -O-ethyl A 0.30 3.5 38 2 0 -O-vinyl 1.10 39 2 0 -O-n-propyl A 0.30 40 2 0 -O-n-pentyl A 2.00 41 2 0 -O-benzyl A 1.80 42 2 0 -O-acetate A 1.20 0.45 8.1 >100 43 3 0 -H A 0.36 0.47 5.2–>50 44 3 0 -OH-epi A 13.2 >50 >50 >50 45 3 0 -O-methyl-epi A 1.9 >50 >50 50 46 3 0 -O-ethyl A 0.03 12.7 2.0 47 3 0 -O-vinyl A 50 14 48 3 0 -O-n-propyl A 0.05 9.3 50 2.6 49 3 0 -O-isopropyl A 0.27 >50 3.6 50 3 0 -O-isopropenyl A 2.85 >50 >50 51 3 0 -O-n-butyl A 0.38 2.5 1.5 52 3 0 -O-n-pentyl A 2.5 53 3 0 -O-allyl A 0.06 >50 11 54 3 0 -O-propargyl A 0.05 >50 10 55 3 0 -O-CH2CF3 A 0.33 25 >50 56 3 0 -O-acetate A 33.0 0.41 >50 >100 22 57 3 0 -O-Me-O-Me 0.17 19 1.8 58 3 0 -Methylene 0.95 2.8 >50 8.9 59 4 0 -H A 4.1 60 4 0 -O-ethyl A 0.24 >50 4.1 61 4 0 -O-acetate A 1.30 0.90 3.5 1.8 62 2 0 ,3 0 ,4 0 -tri-O-ethyl A 0.02 6.8 1.3 63 4 00 -N-ethyl B >50 3.8 64 4 00 -N-ethyl A 0.29 15.2 50 0.3 65 4 00 -N-n-propyl A 0.27 17.3 50 0.35 66 4 00 -N-n-butyl A 14.1 5.3 0.4 67 4 00 -N,N-diethyl >64 4.8 0.3 68 4 00 -OH 3.7 >5 0.4 69 5,6,13,14(a)-TH 35 0.41 70 5,6,13,14(b)-TH >64 45 32 71 13,14-a-Dihydro 4.7 18 72 13,14-b-Dihydro >80 45 >50 73 7,11-Dehydro 0.2 >50 47.4 74 5,6-a-Epoxy 8 0.96 75 5,6-b-Epoxy 0.63 0.96 0.50 76 5,6-DH 0.46 2.4 6.4 0.44 77 5,6-DH, 3 0 -O-ethyl 0.05 15 0.7 78 5,6-DH, 3 0 -O-n-propyl 0.04 1.7 0.4 79 A C17-O-acetate >64 47 47 80 A C17-O-DMAA >64 22 21 81 A C17-O-DMAP 16 9.5 82 A C17-O-DMAB 16.6 8.6 83 A C17-O-NMPipz 2.5 4.7 4 Continued
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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
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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
Page 174 and 175: Table 15 Environmental effects of s
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Page 186 and 187: Three-dimensional quantitative stru
Page 188 and 189: Riddiford, L.M., 1994. Cellular and
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Page 196 and 197: 5 Azadirachtin, a Natural Product i
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Page 208 and 209: et al., 1992). Salehzadeh et al. (2
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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
Page 229 and 230: Figure 4 Spinosad metabolism in avi
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264 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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