Insect Control: Biological and Synthetic Agents - Index of

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Figure 13 Binding to putative cationic subsite in insect nAChR (Kagabu, 1997a). (1997) reported that a nitroenamine isomer (N 3 -free imidacloprid) posseses similar insecticidal activity to imidacloprid (Boëlle et al., 1998). 3.3.4. Physicochemistry of Neonicotinoids The physicochemical properties of the ring system and noncyclic neonicotinoids played an important role in their successful development. In addition, photostability is a significant factor in field performance of this class of insecticides (see Section 3.2). As described (Kagabu and Medej, 1995; Kagabu, 1997a; Kagabu and Akagi, 1997), the energy gap for the different functional groups [›X w Y], from the ground state to the single state, excited in the order [›N w CN] > [›N w NO2] > [›CH w NO2]. For practical application of neonicotinoids, such as for soil and seed treatment, as well as for foliar application, the uptake and translocation in plants is crucial for their insecticidal activity. Thereby, not only the bioisosteric segments of neonicotinoids (see Section 3.3.3.3) but also the whole molecular shape (Figure 12), including the resultant water solubility, has to be considered. Neonicotinoid insecticides are push–pull olefins made up of conjugated electron donating and accepting groups (Kagabu, 1997a). Such polar, nonvolatile molecules have a high water solubility (Table 3) and low POW values compared with other nonpolar insecticidal classes. The following characteristics were described from Kagabu (1997a): 1. Noncyclic neonicotinoids are less lipophilic than the corresponding ring system neonicotinoids. 2. Concerning the functional group [›X w Y] as part of the pharmacophore [ w N w C(E)›X w Y] (iii), water solubility increases in the order of [›CH w NO2] > [›N w CN] > [›N w NO2]. 3. Regarding E, the lipophilicity increased in the order of S > C > O > NH (Kagabu, 1996). Somewhat more lipophilic neonicotinoids should be better for seed treatment application, because uptake by roots is more effective than in the case 3: Neonicotinoid Insecticides 75 of more hydrophilic compounds (Briggs et al., 1982) (Figure 14, Table 3). Due to the excellent systemic properties of neonicotinoids conferred by the moderate water solubility, these insecticides are effective against their main target pests, which are sucking insects, like aphids, leafhoppers, and whiteflies. 3.3.4.1. Physicochemical properties of commercialized neonicotinoids The physicochemical properties of a compound are related to its structural formula. However, it is not possible to predict the behavior of a substance, with sufficient certainity, only on the basis of its formula and physicochemical properties (Stupp and Fahl, 2003). 3.3.4.1.1. Imidacloprid Due to the special moieties like the CPM residue and the 2-(N-nitroimino)imidazolidine 5-ring system, imidacloprid has very weak basic properties under environmental conditions (see Section 3.8.1.2). Water solubility and low partition coefficient in octanol–water are not influenced by pH values between 4 and 9, and at 20 C (Krohn and Hellpointer, 2002) (Table 3). The low partition coefficient of imidacloprid indicates that it has no potential to accumulate in biological tissues and further enrichment in the food chain. The occurrence of imidacloprid in the air is determined by its low vapor pressure of 4 10 10 Pa which excludes volatilization from treated surfaces. The rapid uptake and translaminar transport of imidacloprid from the treated upper leaf side to the lower surface is excellent, as observed in cabbage leaves (Elbert et al., 1991), and in rice and cucumber (Ishii et al., 1994). However, imidacloprid has a considerable acropetal mobility in xylem of plants. In contrast, its penetration and translocation in cotton leaves was less pronounced, as qualitatively reflected by phosphor-imager autoradiography (Buchholz and Nauen, 2001). This xylem mobility makes imidacloprid especially useful for seed treatment and soil application, but it is equally effective for foliar application (Elbert et al., 1991). Due to its lack of any acidic hydrogen, the pKa of imidacloprid is >14, and therefore its transport within the phloem is unlikely, as been shown in several studies (Stein-Dönecke et al., 1992; Tröltzsch et al., 1994). Systemic properties were examined using 14 C-labeled imidacloprid. The translocation of imidacloprid in winter wheat and its uptake and translocation from treated cotton seeds into the growing parts of the cotton plant is described by Elbert et al. (1998). Registered patterns of use of imidacloprid in agriculture now include traditional foliar spray application as well as soil drench application, drip irrigation, trunk (injection) application,
Table 3 Physicochemical properties of commercialized neonicotinoids Physical and chemical properties Color and physical state Colorless crystals Ring systems Noncyclic structures Imidacloprid Thiacloprid Thiamethoxam Nitenpyram Acetamiprid Clothianidin ( )-Dinotefuran Yellow/ crystalline powder Slightly cream/ crystalline powder Pale yellow crystals Colorless crystals Clear/coloress solid powder Melting point ( C) 144 136 139.1 83–84 98.9 176.8 94.5–101.5 Henry’s law constant (Pa m 3 mol 1 ) (at 20 C) 2 10 10
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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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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
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Page 54 and 55: Figure 8 Dihydropyrazole block appe
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Page 60 and 61: Figure 13 Diagrammatic representati
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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 (
Page 84 and 85: Figure 9 Stable conformations and p
Page 88 and 89: Figure 14 Systemicity of neonicotin
Page 90 and 91: site (Kayser et al., 2002). Clothia
Page 92 and 93: Figure 20 Important pest insects ta
Page 94 and 95: Barley yellow dwarf virus vectors s
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Page 102 and 103: 3.8.1. Safety Profile The introduct
Page 104 and 105: Table 7 Environmental profile of co
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Page 112 and 113: Figure 25 Flea control achieved wit
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Page 116 and 117: Brown, J.K., Perring, T.M., Cooper,
Page 118 and 119: In: Ishaaya, I. (Ed.), Biochemical
Page 120 and 121: Léna, C., Changeux, J.-P., 1993. A
Page 122 and 123: patterns in Colorado potato beetle
Page 124 and 125: nach Saatgutbeizung. Pflanzenschutz
Page 126 and 127: 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
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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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