Index

Absolute configuration 152---4 Alfacron 306 Acanthoscelidus obtectus 156 Alkenes 233-5 Acetates 137, 142, 144-6 Alkyne group 149 chemical synthesis of 227-30 Allelochemicals 4 Acetic acid 137, 143 Allomones 4-6 Achroia grisella 81 exploitation of 32 Acoustic signals 80-1 Amauris spp. 43 Acromyrmex octospinosus 57-8 Ambrosia , see Gnathotricus Acyrthosiphon 347 sulcatus Adoxophyes spp. 227 American cockroach, see Periplaneta A. orana 95-6, 266 americana Aedes aegypti 77, 83 Amides 174-5 Aeration, see Isolation methods Anarsia lineatella 336 Affector substances 300, 301 Anastrepha spp. 292 African armyworm 272 A. fraterculus 47, 48 African weaver ant 55-7,59, 123 A. robusta 72, 73 Aggregation pheromones 22-3 A. suspensa 76, 171 anti-aggregation pheromones 345-6 ocellata 351 bark 51-3, 284-5 Anopheles gambiae 83 segetum 17, 86-7, 89, 111, 259 Antennal receptors 9-15 Agrotis ypsilon 76 see also Electroantennography Alarm pheromones 5-6, 23 Antheraea spp. 14, 17 commercial exploitation of 31,347- A. pernyi 13-14 8 A. polyphemus 12-14, 69, 76, 79, 98 exploitation of by other 63---4 Anthonomus grandis (boll weevil) 31-2, multicomponent alarm pheromones 80,269 89 mass trapping 280, 282-3 social insects 53-8 Anti-aggregation pheromones 345-6 Apis mellifera 27 Anti-aphrodisiac pheromones 82-3 Alcohols 136-7, 144-6 Anticarsia gemmatalis 83 chemical synthesis of 227-30 Antimones 4 Aldehydes 137-8, 144-6 Anti-oviposition pheromones 30 chemical synthesis of 227-30 Aonidiella aurantii 161 358 Index

Aonidiella citrina (yellow scale ) tracking movements in still air 161 122-4 pheromone synthesis 243-4 trail bioassays 116-17 23, 31 turning movements of fixed control of 347-8 insects 124-6 see also Individual species wind tunnels 126-30 Aphis fabae 347 electrophysiological methods 109-13 Aphis gossypii 348 electroantennography (EAG) 109- Aphomia sociella 170 12 Aphrodisiac pheromones 22, 40 electromyograms 113 anti-aphrodisiac pheromones 82-3 single-cell recording 112-13 Apis mellifera 23-8 separation problem and 193-4 queen-produced pheromones 23-6 Bioelectrostatic methods 32 worker-produced pheromones 26-8 Black bean 347 Apple maggot 30, 129 Black cutworm 76 Apple moth 95-6 Blatella germanica 76 Arctiidae 43, 45 Bolas spiders 64 Argynnis paphia 39 Boll weevil, see Anthonomus grandis Argyrotaenia velutinana 73, 76, 246, 248 Bombus lucorum 59 Atta spp. 57 Bombus vosnesenskii 62 A. cephalotes 57, 81 Bombyko19, 12, 16,20 A. sexdens 59 chemical synthesis 230-3 A. texana 57, 177 Bombyx mori (silk moth) 9, 12, 16, 20, Attini, see Leaf-cutting ants 230 Australian termite, see Nasutitermes Brevicomin 52-3 exitiosus Bromine 210 Azadirschta indica (neem tree) 32, 349 Brood pheromones 62 Bumble bees 20, 59, 62 Bactrocera, see Dacus Bumble-bee waxmoth 170 Bagworm moth 149 Butterfly orchid 45 Barbara colfaxiana 139, 141 Butyrates 149 Bark beetles 30, 80, 82 aggregation and courtship 51-3, Cabbage looper moth 18, 69, 74, 88,97 284 Cabbage moth 71 mass trapping 283-8 Cabbage white butterflies 22, 30, 39, see also Individual species 346 Bean weevil 156 Cahn-Ingold-Prelog priority system Bee orchids 64 152 Behavioural bioassays, see Bioassays California yellow scale insect 161 Bemisia tabaci 323 Callosobruchus maculatus 347 Benzaldehyde 64 Camponotus spp. 5 Benzene rings 163 C. sericeus 62 Bioassays 105-30, 180 C. vagus 22 behavioural bioassays 113-16 Carbocyclic compounds 163-4, 165-6 activity methods 117 Carboxylic acid 138 olfactometers 119-22 Caribbean fruit fly 76, 81, 171 orientation in mazes 117-19 Carpenter bees 59 index 359

Cataglyphis cursor 22 spirocyclic ketals 235-7 Catalytic hydrogenation 205-6 problems of 226-7 Ceratitis capitata (Mediterranean fruit straight chain compounds 227-33 fly) 6, 23, acetates 227-30 31,48 aldehydes 227-30 control of 300 conjugated dienes 230-3 mass trapping 292-5 monoene alcohols 227-30 monitoring 266, 272 non-conjugated dienes 230 Chemical communication 6-9 Chemoreception mechanisms 16-20 channels of communication 7-14 Cherry fruit fly 30, 295, 346 narrowing of 12 Chilo spp. 314, 326 coding by olfactory receptors 16-20 C. suppressalis 326-8 eusocial insects 23 Chirality 151, 174 noise 8-9 chemical synthesis of chiral silk 9-16 compounds 239-44 Chemical ionization (C1) 199 pheromonal activity and 247-54 Chemical structures see also Optical isomerism branched chain structures 150-63 Choristoneura fumiferana 13, 138, 269- optical activity 151-6 70,274 terpenoids 156-61 Chromatography, see Isolation cyclic structures 163-74 methods carbocyclic compounds 163-4, Chromium (VI) 207 165-6 Chrysoperla carnea 296, 351 heterocyclic compounds 164-71 Cigarette beetle, see Lasioderma polycyclic compounds 169-70, serricorne 171-4 Circadian rhythms 74-5 nitrogen-containing pheromones Citheroniinae 14 174-8 Citral 27, 64 amides 174-5 Classical conditioning 20-1 heterocyclic compounds 176-8 Clearwing moths 85 simple (straight chain) structures Cockroaches 71-2 135-50 see also Periplaneta americana alcohols 136-7 Cocoa pod borer moth 290 aldehydes 137-8 Codlemone 333 double bonds 138-40 Codling moth, see Cydia pomonella esters 137 Coleoptera 22 isomerism 138-41 pheromone structures 157-9 see also Chemical synthesis; see also Individual taxa Structure determination Colias eurytheme 40-1 Chemical synthesis 226-44 Colias philodoce 40-1 branched chain alkenes 233-5 Collembola 59 chiral compounds 239-44 Colorado beetle 17 cigarette beetle 241-2 Column chromatography 188 comstock mealybug 240-1 Common silk moth, see Bombyx mori yellow scale insect 243-4 Common wasp 173 cyclic compounds 235-9 Communication large ring lactones 237-9 acoustic signals 80-1 360 Index

Communication contd mating disruption 332-3 channels of communication 7-14 monitoring 273 narrowing of 12 pheromone isolation examples 211- components of communication 12,216 system 7 role of pheromone blends 88-91 Dacus spp. 173 visual signals 82 D. cucurbitae 174, 292 day-flying 39-40 D. dorsalis 31, 173, 292, 302 see also Chemical communication D. oleae 173, 249 Conopomorpha cramerella 290 lure and kill 300-5 Controlled release devices 266--8 mass trapping 292-5 Corn earworm moth, see Heliothis monitoring 273, 274 Comstock mealybug, see Pseudococcus pheromone synthesis 235-7 cornstockii Damson aphid 347, 349 Coronemata 45, 48 Danaidae 41-3,82, 177 Corpora allata 76 Danaus spp. 43 Corpus cardicum 76 D. glippus berenice 41, 42 Cotton bollworms, see Heliothis spp. D. plexippus 43 Cotton earworm 21 Dendroctonus spp. 51-3, 80, 285, 287 Cotton pests, mating disruption 321-5 D. brevicornis 51-3, 80,345--6,351 see also Heliothis D. frontalis 53, 80, 249, 345, 350 Cotton whitefly 323 D. micans 82, 351 Counter-turning 94-6 D. ponderosae 345 Courtship D. pseudotsugae 80, 345 Diptera 49-51 D. rufipennis 285, 287, 345 Lepidoptera 39-49 Desert locust 38-9, 76--7 aggregations and leks 45-8 Diabrotica barberi 249, 253 noctural Lepidoptera 48-9 Diaeretiella rapae 350 Creatonotus spp. 43, 45 Diastereoisomerism 154-6, 249, 255 Crotalaria 43 (lR)-Z-2,2-Dimethyl-3-(1- Cryptolestes ferrugineus (rusty grain methylethenyl)-cyclobutane• beetle) methanol acetate, synthesis of pheromone isolation example 215 240-1 Cryptophlebia leucotreta (false codling (3S)-3,6-Dimethyl-6-(1-methylethyl)-E- moth) 5,8-decadien-1-o1 pheromone isolation example 215-16 acetate, synthesis of 243-4 Ctenuchiidae 43, 45 4,6-Dimethyl-7-hydroxynonan-3-one Cuckoo ant 63 155,241-3 Culex quinquefasciatus 51 synthesis of 241-2 Cure-lure 292-3 Dimethyldisulphide 209-10 Cyclic structures, see Chemical 1,7-Dioxaspiro[5,5]-undecane 295, 304 structures synthesis of 235-7 Cycnia tenera 81 Diparaopsis castanea 193-4 Cydia nigricana ( moth) 112 Diptera 23 monitoring 266, 268, 269, 273 pheromones of 49-51 pheromone release 70-1 see also Individual taxa Cydia pomonella (codling moth) 74-5 Disparlure 266, 331 Index 361

Displature 28 Eulema cingulata 45 Distillation 187-8 Eumenis semele, see Hipparchia semele Diterpenes 160 Euploea spp. 43 2,2-3,6-Dodecadien-11-olide, synthesis Eurema lisa 41 of 237-9 European com borer 88 2,2-3,6-Dodecadien-12 -olide, synthesis European elm bark beetle 171 of 237-9 European oak leaf-roller 190 Dogbane tiger moth 81 European sawfly 249, 254 Double-bonds 138--41 Eusocial insects, see Social insects beetle 80, 345 Exohormones 6 Douglas fir cone moth 139 Douglas fir tussock moth 149 False codling moth, see Cryptophlebia Drosophila spp. 12,49-51, 81 leucotreta D. borealis 51 Faranal 162, 220-1 D. melanogaster 21, 50 (E)-fS-Farnesene 31, 80, 347, 348 D. stimulans 21 Farnesol 160, 161 Dufour's gland 57, 60-1, 63 Fast atom bombardment (FAB) 199 Fire ants 57, 60-1 Earias insulana 323 Flour moth 21, 350 Earias vitella 317, 323 Foraging Eastern spruce budworm 138 recruitment 60-2 Eciton hamatum 60 trail-following 60-2 Ecitonini 60 Formates 137 Ectatomma ruidum 63 Formic acid 5, 56 Ectohormones 6 Formica pergandei 63 Egyptian cotton leafworm 288, 317 Formica polyctena 22 Eight-toothed engraver beetle 161 Formica rufa 53--4 Electroantennography (EAG) 14--16, Formica subinntegra 63 77, 109-12, 180 Fourier transform (FT) methods 201 electroantennographic detector Fragmentation patterns 196-9 (EAD) 194 Frontalin 53, 249 Electromyograms 113 Functional groups 136, 179 Electron impact (EI) 195, 199 Funnel traps 288-9 Enantiomers 152 Fused rings 171-2 see also Optical isomerism Enoclerus lecontei 351 Gas-liquid chromatography (GLC) Ephestia cautella 281 188-92 Ephestia kuhniella 21, 275-6, 290-1, 350 Geometric isomers 140-1 Epideitic pheromones 30 Geranic acid 27 Epiphyas pastvittana 78, 83 Geraniol 56, 160, 161 Epiplema plagifera 140 German cockroach 76 Epoxides 142, 147-8, 150 Ghost moth 164 epoxidation 210 Glossina spp. 74,307-12 Esters 137, 142, 147, 149 G. morsitans 49, 151, 156, 249, 311 Estigmene acrea 45-58 G. pallidipes 249, 310-11 Ethers 164, 167-8 life cycle 307-8 Euglossinae 45 Gnathotricus retusus 252--4, 255 362 Index

Gnathotricus sulcatus (ambrosia beetle) pheromone isolation example 215 162, 163, 248, synergism 256-8 252-4,255 Heliotropium 43 Golden Malrin 306 Hemiptera 22-3 Gossyplure 142, 321-3, 325 see also Individual taxa Grandlure 32, 80, 282 Hepialus califomicus 164 Grape berry moth 126 Hepialus hecta (swift moth) 164 Grape borer, see Xylotrechus pheromone isolation example 214 pyrrhoderus pheromone structure elucidation Grapholitha spp. 256 221-3 G. funebrana 256 Heterocyclic compounds 164-71 G. jan in thana 256 nitrogen heterocyles 176-8 G. lobarzewski 256 (E)1O-(Z)12-Hexadecadien-1-ol, see G. molesta (oriental fruit moth) 82, Bombykol 83, 139, 141, Z,E-7,11-Hexadecadienyl acetate, 164 synthesis of 230, 231 behaviour in pheromone plume Z,Z-7,l1-Hexadecadienyl acetate, 93,95,98 synthesis of 230,231 mating disruption 334-6 Hexamethyldisilazane 210 pheromone blends 48-9,89-91, Heydenia unica 350 256 High performance liquid pheromone release rate 69 chromatography (HPLC) 192-3 G. prunivora 112 High resolution mass spectrometry Grayling butterfly 20, 39, 40 196-7 Greater grain borer, see Prostephanus Hipparchia semele 20, 39, 40 truncatus Holomelina lamae 69-70, 150 Great peacock moth 3 Homochiral compounds 152 Green bug 347 Homoeosoma electellum 79, 136-7, 140 Green stink bug 22-3, 85-7, 259 Homona coffearia 136, 137 Gregarization pheromone 38 Honey bees 20, 59, 77 Gypsy moth, see Lymantria dispar see also Apis mellifera Gyptol28 Host-plant volatiles 78-80 use in attractants 281 Habituation 78 House flies 23, 49 Hair pencils 41, 43, 45, 48, 82-3 control of 305-7 Harvester ant 61 Hydraecia micacaea 137 Hawthorn leaf-roller 256 Hydrocarbon chains 135-6, 148, 157, Heliconius charitonius 21, 76 178 Heliconius erato 39, 82 4-Hydroxy-1,7- Helicoverpa, see Heliothis dioxaspiro[5,51undecane, Heliothis spp. 274, 316, 321, 323, 325 synthesis of H. armigera 130, 137, 332 235-7 H. phloxiphaga 79 9-Hydroxy-(E)-2-decenoic acid (9- H. virescens 93, IDS, 137, 256-8, 281 HDA) 24-7 H. zea (com earworm) 21, lOS, 337, Hymenitis andromica 82 350,351 host-plant volatiles 79-80 Identification pheromones 59 Index 363

Infra-red spectroscopy 199-201 Ithomiinae 43-5,82 Integrated pest management (lPM) 262 Japanese beetle 249, 281 cotton pests 324 Jasmone 164 Ipsdienol 53, 161, 247, 346 Juvenile hormone 76 Ipsenol161 Ips spp. 51, 53, 80, 288 Kairomones 4-6 I. confusus 350 exploitation of 32, 49 I. pini 107, 258-9 use of by predators and parasites I. typographus 161, 269, 285-8, 35] 63--4 Isobutyrates 149 Keiferia lycopersicella 332, 336-8 Isolation methods 181-94 Ketals 169-70, 172-3 aeration 183-6, 215-16 chemical synthesis 235-7 cold trapping 184 Ketones 142, 147, 149 solid adsorbent 184-6 Kinesis 114 examples 211-16 Kovats system 205 Australian termite 212-13 codling moth 211-12, 216 Lacky moths 22 com earworm 215 Lactones 167-8, 170 false codling moth 215-16 chemical synthesis 237-9 grape borer 216 Large cabbage white butterfly 22 pine emperor moth 213-14 Lasiocampa quercus 3 rusty grain beetle 215 Lasioderma serricorne (cigarette beetle) swift moth 214 155 separation methods 187-94 pheromone synthesis 241-2 bioassays and 193--4 Lasius fuliginosus 11, 62 column chromatography 188 Laspeyresia pomonella, see Cydia distillation 187-8 pomonella gas-liquid chromatography 188- Leaf-cutting ants 31, 57-8, 59, 81, 115 92 behavioural bioassays 114, 119 high performance liquid semiochemical sources 54 chromatography 192-3 see also Individual species thin layer chromatography 188 Leaming 20-3 solvent extraction 182-3 Lekking 45-8 excised gland extraction 183, 213- Lepidoptera 22 14 courtship in 39--49 ovipositor washing 183, 214-15 aggregations and leks 45-8 solvents 186-7 nocturnal Lepidoptera whole body extraction 182-3, pheromones 48-9 211-13 pheromone structures Isomerism females 142-50 geometric isomers 140-1 males 157-60 positional isomers 139 see also Individual taxa see also Optical isomerism Leptinotarsa decemlineata 17 Isoprene 160 Leptopilina heterotoma 21 Isoprene rule 161 Leptothorax acervorum 63 Isovalerates 149 Leptothorax kutteri 63 364 Index

Leptotyphlops blind snakes 5 oriental fruit moth 334-6 Lesser apple worm moth 112 pink bollworm 321-5 81 rice stem borers 326-30 Lestrimelitta limao 64 tomato pinworm 336-8 Light brown apple moth 78, 83 Mating inhibitors 82-3 Limonius can us 138 Matrone 83 Lobesia botrana 126, 317, 318 Mazes 117-19 Locusta migratoria 38 Mealworm beetle 82 Lure and kill techniques 300-12 Mediterranean flour moth 290-1 examples Mediterranean fruit fly, see Ceratitis house flies 305-7 capitata tephritid fruit flies 300-5 Meliponini 64 tsetse flies 307-12 Melon fly 174 general principles 300 Metal hydride reduction 206 sprayable formulations 304-5, 307 Methoxymercuration 208-9 target devices 302-4, 308-12 Methylcydohexenone (MCH) 345 toxic baits 31, 306-7 1-Methylethyl (E,E)-2,4-dimethylhepta- Lymantria dispar (gypsy moth) 78, 81, 2,4-dienoate, 150,281 synthesis of 233-5 bioassays 113, lIS, 128 Methyleugenol31,292-3,302 control of 28 Mevalonic acid 160 mating disruption 330-2 Microplitis croceipes 21 monitoring 266, 269, 272 Mocis disseverans 73 Monarch butterfly 43 Malacasoma spp. 22 Monitoring 29, 263-76 Male repellents 82-3 components of monitoring system Mamestra spp. 163 265-70 M. brassicae 71 attractant source of lure 265-8 Manganese dioxide 207-8 controlled release devices 266-8 Marking pheromones 59 trap design 268-70 Mass spectrometry (MS) 194-9 factors influencing trap catch 270-1 coupled GC-MS 199 pest biology influence on catch Mass trapping 29-30, 280-96 interpretation 271 attractant source 280-1 trap placement 270-1 examples practical and commercial factors bark beetles 283-8 264-5 moth pests 288-91 scientific factors 263-4 tephritid fruit flies 292-6 uses of monitoring systems 264, trapping system 281 272-6 trap saturation problem 282-3 arrival of pests in pest-free areas Mastogophora corniger 64 272-3 Mating disruption 30, 314-38 early warning of pest incidence delivery system 316-19 272 evaluation of treatments 319-21 effects of control measures 275-6 examples population density correlations codling moth 332-3 274-5 gypsy moth 330-2 population trends 274 Index 365

risk assessment 274 N. cytherea cytherea (pine emperor survey to define infested areas moth) 149, 206 272 pheromone isolation example timing of other sampling methods 213-14 273 timing of spray treatments 273 Oak eggar moth 3 Monomorium pharaonis (Pharaoh's ant) Odour plume 91-8 162, 178 Oecophylla longinoda 55-7, 59, 123 pheromone structure elucidation Olenopsis spp. 57 219-21 Olfactometers 119-22 Monoterpenes 160 Olfactory conditioning 21 Mosquitoes 51, 74, 77, 83 Olive fly, see Dacus oleae Mountain pine beetle 345 Olive moth 275 Musca domestica 49 Ophrys spp. (bee orchids) 64 control of 305-7 Optical isomerism 83-4, 151-6 Muscalure 306 absolute configuration 152-4 Muscamone 306 diastereoisomerism 154-6 Myrmecia gulosa 5 pheromonal activity and 247-54 Myzus persicae 31, 347, 348 see also Chirality Organochlorines 261 Nasonov gland 27 Oriental fruit fly 173, 292, 302 Nasutitermes costalis 119 Oriental fruit moth, see Grapholitha Nasutitermes exitiosus (Australian molesta termite) 206 Oriental hornet 170 pheromone isolation example 212- Orientation 114-15 13 in mazes 117-19 pheromone structure elucidation trail-following 61-2 218-19 Oryzaephilus surinamensis (saw-toothed Necrophilus spp. 11 grain beetle) Neem tree 32, 349 171 Neivamyrex 5 pheromone synthesis 237-9 Neocembrene-A 206, 207, 218-19 Osrina nubilalis 88 Neodiprion sertifer 249, 254 Oviposition inhibition 30, 51, 346-7 Nepetalactol347 Oviposition pheromones 22, 51 Nepetalactone 347 9-0xo-(E)-2-decenoic acid (9-ODA) Nephila 45 24-8 Nerol56 Ozonolysis 207 Nezara viridula 22-3, 85-7, 259 12 Pacific coast wireworm 138 Noise 8-9 Palm weevils 281 North American bark beetle 2580259 Panolis flammea 89 Northern com rootworm 249, 253 Papaya fruit flies 80 Novomessor albisetosus 81 Parapheromones 6, 292, 302 Novomessor cockerelli 81 Parasites 63-4, 350-1 Nuclear magnetic resonance Paravespula vulgaris 173, 174 spectroscopy (NMR) 201-4 Passion vine butterflies 21, 39, 82 Nudaurelia spp. 14 Pea aphid 347 366 Index

Peach potato aphid 347 role in communication 88-91 Peach tree borers 335 pheromone plume 91-8 Peach twig borer 336 release rates 69-74 Peacock moths 3 see also Chemical structures; Pea moth, see Cydia nigricana Chemical synthesis; Pectinophora gossypiella (pink Pheromonal activity bollworm) 95, 142,230, Philanthus triangularum 63 314 Phlogophora meticulosa 45 mating disruption 317, 318, 321-5 Phthorimaea operculella 91, 140 pheromone blends 87-8 Pieris brassicae 22, 30, 346 pheromone structure elucidation Pieris rapae 30, 39, 346 217-18 Pine beauty moth 89 Periplaneta americana (American Pine emperor moth, see Nudaurelia cockroach) 17, 19 cytherea cytherea bioassays 111, 117, 120--1, 124 Pink bollworm moth, see Pectinophora Periplaneta australasiae 117, 120 gossypiella Periplanone 17, 117 Pinus ponderosa 51 Permanganate (Mn(Vll)) 210 Plant interactions Pharaoh's ant, see Monomorium host-plant volatiles 78-80 pharaonis pyrrolizidine alkaloid-containing Phase change 38 plants 43-5 Pherodon humuli 347, 349 Platynota stultana 336 Pheromonal activity Plum fruit moth 256 chirality and 247-54 Pogonomyrmex badius 61 geographical variation 258--60 Polistes annularis 59 structural variation and 246--7 Polistes fuscatus 59 synergism 254-60 Polistes metricus 59 Pheromone parsimony 23 Polycyclic compounds 169-70, 171-4 Pheromone responses Polygodial 349 circadian changes in thresholds 74-5 Popillia japonica 249, 281 pre-exposure and 77-8 Porthetria dispar, see Lymantria dispar relationships with other stimuli 78- Positional isomerism 139 83 Potato stem borer 137 acoustic stimuli 80--1 Potato tuberworm moth 91,140 anti-aphrodisiac pheromones 82-3 Prays citri 266 host-plant volatiles 78-80 Prays oleae 266, 275 male repellents 82-3 Predators 63-4, 351 visual signals 82 Primer pheromones 4, 38-9 release rates and 69-74 Priority rules 152-4 sexual maturity and 76--7 Propaganda pheromones 64 Pheromones 4 Propanoates 137 categories of 5-6 Prostephanus truncatus (greater grain definition of 105 borer) 202 parapheromones 6, 292, 302 pheromone synthesis 233-5 pheromone blends 83-5 Pseudaletia unipunctata 83 population and genetical variation Pseudococcus cornstockii (comstock 85-8 mealybug) 162 Index 367

pheromone synthesis 240-1 (SIMS) 199 Pseudoplusia includens 149 Semiochemicals 4-6 12 categories of 4-6 Pyrrharctia isabella 70 Senecio 43 Pyrrolizidine alkaloids (PAs) 43-5, 46 Sensory filtering 11-12 Separation methods, see Isolation Queen butterfly 41, 42 methods Queen substance 24-6, 27 Serricornin, synthesis of 241-2 Servosphere 124-5 Racemic mixtures 83, 152 Sesiidae 85 Recruitment 60-2 Sesquiterpenes 160 Redbanded leafroller moth 73, 76, 246, Sexual maturation 38-9,76-7 248 Sexual pheromones 6, 22-3 Red bollworm 193-4 commercial exploitation of 347-8 Red flour beetle 162, 248-9 see also Aphrodisiac pheromones Red scale insect 161 Silk moths 76, 109 Redundancy 8 chemical communication 9-16 Releasers 4 Silkworm moth, see Bombyx mori Reticulitermes flavipes 63 Silver-washed fritillary 39, 40 Retinue behaviour 25 Silver-Y moth 76 Rhagoletis spp. 292 Single-cell recording 112-13 R. cerasi 30, 295, 346 Small ermine moths 79, 84-5 R. pomonella 30, 129, 346 Small sulphur butterfly 41 Rhizophagus grandis 82, 351 Social insects 23 Rhopalosiphum padi 349 pheromones of 53-62 Rhyncophorus spp. 281 alarm and defence 53-8 Rhytodoponera metallica 177 brood pheromones 62 Rice stem borers 314 marking and identification 59 mating disruption 326-30 recruitment and orientation 60-2 Risk assessment 274 see also Apis mellifera Rusty grain beetle, see Cryptolestes Solenopsis spp. 60-1 ferrugineus S. geminata 61 S. invicta 61, 171 Saltmarsh caterpillar moth 45-8 S. saevissima 60, 61 Saturnia pyri 3 Solvent extraction, see Isolation Saturniidae, see Silk moths methods Saw-toothed grain beetle, see Southern pine beetle 80, 249, 345 Oryzaephilus looper 149 surinamensis Spectroscopy, see Structure Schistocerca gregaria 38-9, 76-7 determination Schizaphus graminum 347 Spilosoma congrua 72-3 Scirpophaga spp. 314, 326, 328 Spiny bollworm 323 S. incertulas 329 Spirocyc1ic compounds 173-4 S. innotata 329 chemical synthesis 235--7 Scolytidae, see Bark beetles Spodoptera exempta 272 Scolytus muItistriatus 171, 269 Spodoptera exigua 337 Secondary ion mass spectrometry Spodoptera /ittoralis 288, 317, 323 368 Index

Spodoptera litura 17 lure and kill techniques 300-5 Spotted bollworm 323 mass trapping 292-6 Spotted cow pea bruchid 347 see also Individual species Spruce bark beetle 285,345 Terpenoids 156-61 Sticky traps 294-6 acyclic terpenoid pheromones 158- Stimulo-deterrent methods 31-2, 348-9 60,161-3 Stridulation 80,81 Z,Z-5,8-Tetradecadien-13-olide, Structure determination 194-211 synthesis of 237-9 chemical methods 205-11 Z-9-Tetradecenyl acetate, synthesis of bromine 210 227-30 catalytic hydrogentation 205-6 Tetramoriini spp. 164 chromium (VI) 207 Tetranychus urticae 334 dimethyldisulphide 209-10 Thanasimus 288 manganese dioxide 207--8 Thanatophilus spp. 11 metal hydride reduction 206 Thermoregulatory pheromones 62 methoxymercuration 208-9 Thin layer chromatography (TLC) 188 ozonolysis 207 Thyridopteryx ephemeraeformis 149 permanganate (Mn(VII» 210 Tiger moth 150 examples 217-23 Tobacco budworm 105, 137, 256--8 Australian termite 218-19 Tomato pinworm 332, 336--8 pharaoh's ant 219-21 Tortricidae 12, 75, 85 pink bollworm moth 217-18 Tortrix viridiana 190 swift moth 221-3 Toxic baits, see Lure and kill physical methods 194-205 techniques infra-red spectroscopy 199-201 Toxotrypana curvicauda 80 mass spectrometry 194-9 Trail bioassays 116--17 nuclear magnetic resonance Trail-following 60-2 spectroscopy (NMR) Trail pheromones 57 201-4 exploitation of 31 ultraviolet-visible spectroscopy Trapping, see Mass trapping; 201 Monitoring Sulcatol 163, 248, 252, 255 Tribolium castaneum 162, 248-9 Sunflower moth 79, 136--7, 140 Trichogramma 71, 350 Swift moth, see Hepialus hecta T. evanescens 350 Synanthedon exitosa 335 Trichoplusia ni 18, 69, 74, 88, 97 Synanthedon pictipes 335 Trichopoda pennipes 87,350 Synergism 254-60 Tricopenius spp. 63 Synomones 4 (Z)-Tricosene 49,50-1,306--7 Trigona spp. 64 Tandem running 62 T. angustula 64 Target devices 302-4 T. postica 62 Taxes 114 T. subterranea 64 Tea tortrix moth 136, 137 Trimedlure 6, 31, 266, 292-4 Temnochila chloridia 351 Tripetidae, see Tephritidae Tenebrio molitor 82 Trogoderma spp. 151, 154 Tent caterpillars 22 True army worm 83 Tephritidae 23, 48, 51, 73, 281 Tsetse flies 23, 49, 74, 77, 151, 156 Index 369

control of 307-12 day-flying Lepidoptera 39-40 life cycle 307-8 see also Glossina spp. Western pine beetle 345 Turnip moth 17, 86-7, 259 Wind tunnels 126-30 Turpentine 80, 156 Wood ant 53-4

Ultrasound clicks 81 Ultraviolet-visible spectroscopy 201 Xylotrechus pyrrhoderus (grape borer) Undecane 56 153, 154-5 Utetheisa 43 pheromone isolation example 216 Utetheisa ornatrix 70 UV reflectance patterns 40, 41 Yellow scale insect, see Aonidiella citrina Z-Vaccenyl acetate 51 Y-maze bioassays 117-19, 124 Valerates 149 Yponomeuta spp. 79,84-5 Velvetbean caterpillar moth 73, 83 Y. cagnatellus 84 Venturia (Nemeritis) canescens 21, 350 y. evonymellus 84 Verbeno153 y. padellus 84 Verbenone 53, 345-6 y. plumbellus 84 Vespa orientalis 170 Y. rorellus 84-5 Vespinae 62 Y. viginpunctatus 84 Visual signals 82 Yponomeutidae 84