Insect Control: Biological and Synthetic Agents - Index of

More documents

Recommendations

Info

Table 9 Continued Lu-chu 2001 Field Azadirachtin Leaf dip >1000 Blattella germanica Apyr-R Field Permethrin Topical 97 Wei et al. (2001) Apyr-R Field Deltamethrin Topical 480 Apyr-R Field Spinosad Topical 1.3 Musca domestica AVER Field Abamectin Topical >1000 Scott (1998) AVER Field Spinosad Topical 1.9 LPR (Multi-R) Field–Lab. Spinosad Topical 4.3 OCR (cyclodiene) Cyclodiene Topical high OCR (cyclodiene) Spinosad Topical 0.4 Cornell-R Field-Lab. Spinosad Topical 0.9 R12 (CYP6D1) Laboratory Spinosad Topical 1.8 R3 (kdr and pen) Laboratory Spinosad Topical 1.4 Musca domestica ALHF (multi R) Field Permethrin Topical 1800 Liu and Yue (2000) ALHF (multi R) Field Cypermethrin Topical 4200 ALHF (multi R) Field Spinosad Topical 1.4 Musca domestica Several Field Permethrin Glass high Scott et al. (2000) Several Field Cyfluthrin Glass high Several Field Spinosad Feeding low Several Field Fipronil Glass very low Several Field Dimethoate Glass low Several Field Methomyl Feeding low-high Choristoneura rosaceana Choristoneura rosaceana Choristoneura rosaceana 6: The Spinosyns: Chemistry, Biochemistry, Mode of Action, and Resistance 235 Species Strain Select Compound Method Berrien Field Azinphosmethyl Diet 27 Ahmad et al. (2002) Berrien Field Chlorpyrifos Diet 25 Berrien Field Spinosad Diet 0.83 Berrien Field Cypermethrin Diet 8 Berrien Field Methoxyfenozide Diet 3.1 Berrien Field Indoxacarb Diet 705 Site 2 Field Azinphosmethyl Leaf disc 15.5 Smirle et al. (2003) Site 2 Field Spinosad Leaf disc 1.8 Brown 97 (OP-R) Field Tebufenozide Leaf dip 12.8 Waldstein and Reissig (2000) Brown-96 (OP-R) Field Spinosad Leaf dip 2.0 sites were also shown to exhibit significant levels of resistance to spinosad that increased with time and were associated with failures to control P. xylostella larvae in the field (Zhao et al., 2002). As a response to these developments, a regional IRM program was implemented (Zhao et al., 2002; Mau and Gusukuma-Minuto, 2004). Spinosad was voluntarily withdrawn from use where field failures had occurred and two newly registered products, emamectin benzoate and indoxacarb, were put into a rotation scheme (Mau and Gusukuma-Minuto, 2004). Following its withdrawal from use, susceptibility to spinosad increased rapidly such that for some of the locations (Maui and Hawaii) the thresholds for spinosad reintroduction were met within 6-8 months, setting the stage for spinosad’s reintroduction in early 2002 (Mau and Gusukuma-Minuto, 2004). By the fall of 2002, resistance to spinosad had also fallen below the threshold in the remaining region (Oahu) such that it was reintroduced in Toxicity ratio Reference early 2003 (Mau, personal communication). With its reintroduction, spinosad has become part of an IRM rotation scheme that also includes emamectin benzoate and indoxacarb (Mau, personal communication). Given the selection pressure that was placed on spinosad in several of the locations in Hawaii, it is not clear how long this rotation scheme will remain effective in the control of a pest that has developed resistance to virtually all insecticides previously used. Nevertheless, this experience with spinosad in Hawaii has demonstrated that IRM can indeed help extend, if not preserve, the life of an insect control agent. 6.7. Spinosyns and Spinosoid Structure–Activity Relationships Exploration of the spinosyns included continued isolation and identification of new spinosyns (naturally occurring analogs of spinosyn A). This effort
236 6: The Spinosyns: Chemistry, Biochemistry, Mode of Action, and Resistance ultimately led to the isolation more than 20 new spinosyns from S. spinosa (see Section 6.2.1), and an expanding number from S. pogona (Hahn et al., 2002; Lewer et al., 2003). At the same time, running in parallel with the spinosyn isolation program, was a long-standing effort aimed at the preparation of semisynthetic derivatives/analogs of the spinosyns, termed spinosoids. In light of the excellent activity against lepidopterans and the desire for greater utility, the spinosoid synthesis program had two goals. The first was to increase activity against lepidopterans, typically using H. virescens larvae as an indicator species. The second goal was, if possible, to expand the spectrum of this unique chemistry. To date, the total number of spinosyns and spinosoids resulting from this long-standing and continuing effort easily exceeds 1000 molecules, the vast majority being spinosoids. Chemistry around the spinosyns has been focused on modifications to various functionalities in the spinosyn structure, which has been both limited by and facilitated by the novel chemical nature of these molecules. These modifications can loosely be grouped into: . modifications of the tetracycle, . modification/replacement of the forosamine sugar, and . modification/replacement of the tri-O-methyl rhamnose sugar. Due to limited quantities of starting material, initial modifications to the spinosyn structure were limited to relatively simple or straightforward modifications, most often associated with a reduced level of activity. Later modifications did ultimately succeed in devising spinosoids that were more active than the naturally occurring spinosyns (Sparks et al., 2000a, 2001; Crouse et al., 2001). 6.7.1. Modifications of the Tetracycle The tetracycle of spinosad is a rather rigid structure, the shape of which is influenced, in part, by the conjugated 13,14 double bond. Hydration of the 13,14 double bond (compounds 71 and 72) alters the three-dimensional shape of the tetracycle, which is associated with a reduction in activity (Crouse and Sparks, 1998; Crouse et al., 1999) (Table 3). The 13,14-a-dihydro (compound 71) results in less of a conformational change and hence less of a distortion than the corresponding 13,14-b-dihydro (compound 72), which is reflected in the better activity of the a-analog (Table 3). Not surprisingly, reduction of both the 5,6 and 13,14 double bonds (compounds 69 and 70) reduces activity against H. virescens larvae (Crouse et al., 1999) and is neutral to negative for stable flies (Kirst et al., 2002a) and mites (Table 3). In contrast, a reduction of only the 5,6 double bond (compound 70) has little effect on the three-dimensional shape or on activity towards H. virescens larvae, but reduces activity to stable flies, and is associated with an increase in activity against aphids and mites (Crouse et al., 2001) (Table 3). Likewise, the 5,6-b-epoxy analog of spinosyn A is about as active against H. virescens larvae as spinosyn A, while the 5,6-a-epoxy analog (compound 74) is much less active (Table 3). Both 5,6-epoxides are slightly less effective against stable fly adults compared to spinosyn A, while the 5,6-bepoxy analog is, just like the 5,6-dihydro derivative (compound 74), more active against mites (Table 3). Thus, for larvae of H. virescens and stable fly adults, alteration of the 5,6 double bond provides no improvement in activity, while some interesting increases in activity are noted for T. urticae (Table 3). In general, for H. virescens larvae, any modification to the internal structure of the tetracycle reduces activity (Crouse et al., 1999), with the exception of the addition of extra unsaturation at the 7–11-position of spinosyn D (compound 73), which is about as active as spinosyn A (Table 3). Many other synthetic modifications have been made to the tetracycle (Crouse and Sparks, 1998; Crouse et al., 1999) but none has provided a significant overall improvement in biological activity. Where chemical synthesis has been unable to thus far succeed, mother nature, and the genetic manipulation thereof, have been able, in part, to fill the gap. Extension of the alkyl group at C21 to n-propyl (compound 30), produced through alteration of polyketidesyntase (PKS) modules (Burns et al., 2003), provides a slight improvement in activity over spinosyn A against H. virescens larvae and aphids (Table 3). Further extension of the C21 position to 21-butenyl (compound 31), the primary factor produced by S. pogona (Lewer et al., 2003), provides activity against H. virescens equivalent to spinosyn A. However, for Aphis gossypii, activity is further improved over C21-n-propyl (compound 30) (Table 3). Unfortuantely, as with the other modifications that have improved intrinsic aphid and mite activity, the physical properties of the spinosyns thus far discovered generally preclude the effective plant mobility and residuality necessary for effective control of aphids or mites in the field (Crouse et al., 2001). 6.7.2. Modification or Replacement of the Forosamine Sugar As described above (see Section 6.7.1) for the spinosyns, removal of a methyl group from the forosamine nitrogen tends to be a fairly neutral
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 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
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 86 and 87:
Figure 13 Binding to putative catio
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
Page 96 and 97:
investigate the mode of action of n
Page 98 and 99:
within the desensitized state over
Page 100 and 101:
the accumulation of this acid in th
Page 102 and 103:
3.8.1. Safety Profile The introduct
Page 104 and 105:
Table 7 Environmental profile of co
Page 106 and 107:
substance is bound irreversibly to
Page 108 and 109:
imidacloprid conferring a high leve
Page 110 and 111:
nAChR are comparable to the efficac
Page 112 and 113:
Figure 25 Flea control achieved wit
Page 114 and 115:
and the resolution of FAD was teste
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
Page 134 and 135:
The molting process is initiated by
Page 136 and 137:
Table 1 Bisacylhydrazine insecticid
Page 138 and 139:
4.2.2. Bisacylhydrazines as Tools o
Page 140 and 141:
to the three EcRs with either muris
Page 142 and 143:
of action of ecdysone agonists was
Page 144 and 145:
thus inducing effects and symptomol
Page 146 and 147:
and microsomes. Subsequently, Willi
Page 148 and 149:
dipteran insects, like the midge, C
Page 150 and 151:
eetle (Exomala orientalis) when app
Page 152 and 153:
metabolic fate studies showed the i
Page 154 and 155:
y specific proteins in signaling pa
Page 156 and 157:
their reduced risk for the environm
Page 158 and 159:
can be reversed by applying JH. JH
Page 160 and 161:
door for a more rational approach t
Page 162 and 163:
apparent that it was a bHLH-PAS and
Page 164 and 165:
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
Page 170 and 171:
Flucycloxuron Nonsystemic acaricide
Page 172 and 173:
The discovery of diflubenzuron spaw
Page 174 and 175:
Table 15 Environmental effects of s
Page 176 and 177:
ecessive (R male S female) manner,
Page 178 and 179:
esistance management programs due t
Page 180 and 181:
IPS Paraconfusus lanier (Coleoptera
Page 182 and 183:
larvae parasitized by Microplitis r
Page 184 and 185:
Kostyukovsky, M., Chen, B., Atsmi,
Page 186 and 187:
Three-dimensional quantitative stru
Page 188 and 189:
Riddiford, L.M., 1994. Cellular and
Page 190 and 191:
characterization of resistant clone
Page 192 and 193:
Biological Approaches to Pest Contr
Page 194 and 195:
M389 L308 M272 T304 T393 V404 L420
Page 196 and 197: 5 Azadirachtin, a Natural Product i
Page 198 and 199: and Hemiptera and was related to ef
Page 200 and 201: eported, but this is rather nonspec
Page 202 and 203: important source of pest control at
Page 204 and 205: effects with physiological effects
Page 206 and 207: eing associated with an accumulatio
Page 208 and 209: et al., 1992). Salehzadeh et al. (2
Page 210 and 211: ehavior of Spodoptera littoralis (p
Page 212 and 213: indica A. Juss. IBH Publishing Comp
Page 214 and 215: Smith, S.L., Mitchell, M.J., 1988.
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 227 and 228: 216 6: The Spinosyns: Chemistry, Bi
Page 229 and 230: Figure 4 Spinosad metabolism in avi
Page 245: 234 6: The Spinosyns: Chemistry, Bi
Page 255 and 256: A6 Addendum: The Spinosyns T C Spar
Page 257 and 258: 246 A6: Addendum Scott, 2008) and i
Page 259 and 260: 248 7: Bacillus thuringiensis: Mech
Page 289 and 290: A7 Addendum: Bacillus thuringiensis
Page 291 and 292: 280 A7: Addendum toxins is magnitud
Page 293 and 294: This page intentionally left blank
Page 295 and 296: Table 1 Comparative properties of s
Page 297 and 298:
286 8: Mosquitocidal B. sphaericus:
Page 299 and 300:
Page 301 and 302:
Page 303 and 304:
Page 305 and 306:
Page 307 and 308:
Table 4 Characteristics of various
Page 309 and 310:
Page 311 and 312:
Page 313 and 314:
Page 315 and 316:
Page 317 and 318:
Page 319 and 320:
A8 Addendum: Bacillus sphaericus Ta
Page 321 and 322:
310 A8: Addendum essential to devel
Page 323 and 324:
This page intentionally left blank
Page 325 and 326:
314 9: Insecticidal Toxins from Pho
Page 327 and 328:
Page 329 and 330:
Page 331 and 332:
Page 333 and 334:
Page 335 and 336:
Page 337 and 338:
Page 339 and 340:
A9 Addendum: Recent Advances in Pho
Page 341 and 342:
330 A9: Addendum Lee, S.C., Stoilov
Page 343 and 344:
332 10: Genetically Modified Baculo
Page 345 and 346:
Page 347 and 348:
Page 349 and 350:
Page 351 and 352:
Page 353 and 354:
Page 355 and 356:
Page 357 and 358:
Page 359 and 360:
Page 361 and 362:
Page 363 and 364:
Page 365 and 366:
Page 367 and 368:
Page 369 and 370:
Page 371 and 372:
Page 373 and 374:
Page 375 and 376:
Page 377 and 378:
Page 379 and 380:
Page 381 and 382:
Page 383 and 384:
Page 385 and 386:
Page 387 and 388:
Page 389 and 390:
Page 391 and 392:
Page 393 and 394:
Page 395 and 396:
384 A10: Addendum cysteine protease
Page 397 and 398:
Page 399 and 400:
388 11: Entomopathogenic Fungi and
Page 401 and 402:
Page 403 and 404:
Page 405 and 406:
Page 407 and 408:
Page 409 and 410:
Page 411 and 412:
Page 413 and 414:
Page 415 and 416:
Page 417 and 418:
Page 419 and 420:
Page 421 and 422:
Page 423 and 424:
Page 425 and 426:
Page 427 and 428:
Page 429 and 430:
Page 431 and 432:
Page 433 and 434:
Page 435 and 436:
Page 437 and 438:
Page 439 and 440:
Page 441 and 442:
Page 443 and 444:
Zare, R., Gams, W., Culham, A., 200
Page 445 and 446:
434 A11: Addendum although a number
Page 447 and 448:
436 A11: Addendum Examination of ge
Page 449 and 450:
Page 451 and 452:
440 12: Insect Transformation for U
Page 453 and 454:
Page 455 and 456:
Page 457 and 458:
Page 459 and 460:
448 A12: Addendum genetic transform
Page 461 and 462:
Page 463 and 464:
452 Subject Index Aphis gossypii (c
Page 465 and 466:
454 Subject Index Bisacylhydrazine
Page 467 and 468:
456 Subject Index Cry toxins (conti
Page 469 and 470:
458 Subject Index Entomopathogenic
Page 471 and 472:
460 Subject Index Homoptera molting
Page 473 and 474:
462 Subject Index Kinoprene (ENSTAR
Page 475 and 476:
464 Subject Index Muscle(s) sodium
Page 477 and 478:
466 Subject Index Photorhabdus (con
Page 479 and 480:
468 Subject Index Sodium channel bl
Page 481:
470 Subject Index Toxocara cati, im
show all

Insect Control: Biological and Synthetic Agents - Index of

Create successful ePaper yourself

Delete template?

Save as template?