1655

Index

a abamectin 1495 physico‐chemical biological activity 1593–1594 properties 1273–1274 mites and insects 1488 acetoacetate 328, 686, 1164, 1171 mode of action 1592–1593 acetochlor 274, 375, 431, 468, 469, nematicidal seed treatment 1593 473, 564 abamectin, crop protection 1496 acetogenin 614 abiotic stress 571, 574, 577, 579, 828, acetohydroxyacid synthase (AHAS) 3, 959, 960, 1328, 1330 8, 18, 33–51, 55, 72, 97, 109, 122, abscisic acid (ABA) 305, 351, 573 152 acaricidal 614, 662–664, 706, 718, 734, binding site of 40–45 736, 992, 1092–1095, 1156, 1163, crops engineered resistance 50–51 1171, 1173–1176, 1178, 1181, flavin adenine dinucleotide 1184, 1186, 1204, 1490, 1529 (FAD) 36 carboxamides 1176 herbicides target 39–40 acaricide 627 heterotetramer subunits 36 cross‐resistance 1177–1178 HEThDP 34 in vitro selectivity 1179–1180 inhibitors 18–19 IRAC classification 1180–1181 molecular basis for 45–48 lead compound 1174–1175 subunit structure 37–39 mechanisms 1156 ThDP 34 mode of action 1178–1179 weed resistance 48–50 structure–activity relationship acetolactate 33 (SAR) 1176–1177 acetolactate synthase (ALS) synthesis 1177 Alopecurus myosuroides 13 toxicity 1178 herbicides 331 acaricide pyflubumide 1177 inhibitors 346, 532 accessory proteins 392, 1543 pyrimidinylcarboxylate acequinocyl 1176, 1181–1182, 1189 inhibitors 128 acetamides 9, 11, 359, 398 acetylcholine (ACh) 1229, 1348 acetamiprid 1273–1276 acetylcholine binding proteins chemical classification (AChBPs) 1233, 1240, 1288 of 1273–1274 acetylcholine esterase (AChE) 1242, insecticidal activity 1275 1244–1245, 1591

Modern Crop Protection Compounds, Third Edition. Edited by Peter Jeschke, Matthias Witschel, Wolfgang Krämer, and Ulrich Schirmer. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA. Published 2019 by Wiley-VCH Verlag GmbH & Co. KGaA.

bindex.indd 1655 12/21/2018 3:11:03 PM 1656 Index

® acetyl‐CoA carboxylase Acuron 204, 274, 278, 429, 430 (ACCase) 1207–1211 acylation 138, 278, 396, 513, 850, 861, carboxylate transferase (CT) 950, 951, 1017, 1019, 1096, 1207, function 501 1214, 1626 chemical classes of 16 acyl carrier protein (ACP) 353, 1416 commercialised ACCase 2‐Acylimino‐3‐phenylthiazolines 231 aryl‐1,3‐diones (DENs) 510 Aedes aegypti 1024, 1025, 1073, 1077, aryloxyphenoxypropionates 1361, 1453 (AOPPs/fops) 507–508 aflastatin A 882 cyclohexanediones (CHDs/ agonists vs. antagonists 1254–1255 dims) 508–510 Agriotes spp. 1303, 1464 dicot tolerance 501 Agrobacterium 456, 461, 1104, 1106 inhibitors 253 agrochemical fungicides 728 IPM AKD‐1022 1316–1317 ® Envidor 1211–1212 Alabama argillarcea 1465 ® Oberon 1211–1212, 1218 AlionTM 407 multisubunit and multifunctional alkaloid ryanodine 993, 1541, 1568 enzyme 502 alkylazines patent applications biology of 406–407 2‐aryl‐cyclohexane‐1,3‐dione chemistry of 403–406 derivatives 517–519 2‐alkylthio‐3‐aminobenzoic acids 965 2‐aryl‐cyclopentane‐1,3‐ alkynyl amide 791 diones 511–517 4‐alkynyl‐2‐anilinopyrimidines 751 aryl pyran‐and piperidine‐ allosteric modulators 993, 1224, diones 520–524 1400–1418, 1455, 1478–1497 2‐aryl‐pyrazolo‐1,3‐ alloxydim‐sodium 934 diones 524–525 allylamines 604, 802, 838, 839 2‐aryl‐pyridazine‐1,3‐diones 525 Alopecurus myosuroides 13, 17, 64, 69, 2‐aryl‐tetramic and 2‐aryl‐tetronic 119–121, 151, 364, 446, 507 acids 519–520 Amaranthus in plants 503 A. palmeri 13, 203, 376, 464 resistance 507 A. tuberculatus 19, 203, 299, 464 spirodiclofen Amblyomma americanum 1282 cyclic ketoenols 1202–1205 ametoctradin 601, 634, 636, 665, 667, synthesis of 1206–1207 674, 793 spiromesifen amicarbazone cyclic ketoenols 1202–1205 active ingredient, discovery discovery of 1212–1214 of 560–562 mode of action 1216–1218 biological behavior 564 synthesis of 1206–1207 metabolites 564 transcarboxylation reaction 502 physico‐chemical properties 559 acetyl‐coenzyme A (acetyl‐CoA) 1631 synthesis 562–563 ACh‐binding site 1233 amidoflumet acibenzolar‐S‐methyl 959, 966–967 biology and biochemistry 1529 synthesis 965–966 discovery and systemic acquired resistance development 1527–1529 induction 966–967 registration 1529

bindex.indd 1656 12/21/2018 3:11:04 PM Index 1657

structure of 1528 derivatives 1520 synthesis of 1528 structure‐activity 1519 amino acid amides 4‐aminoquinolines 734–738 aminosulfones 854–856 aminosulfones 845, 854–856 benthiavalicarb 852–853 4‐amino‐1,2,4‐triazine‐5‐ones 560 iprovalicarb 850–852 amisulbrom 634, 636, 665, 666, 674, N‐sulfonyl amino acid amides 856 793 valifenalate 853–854 ammonium thiosulfate (ATS) aminoalkylpyrimidines 575, 577 diflumetorim 729 anacardic acids 709, 1149 structure–activity relationship aniline 110, 152, 402, 686, 687, 689, (SAR) 731 752, 757, 834, 926, 943, 951, structure of class 729 1177, 1527, 1552, 1553, 1563 5‐amino‐3‐cyano‐pyrazole 1461 anilinopyrimidines (APs) 595, 600, aminocyclopyrachlor 602 chemical and physical 4‐alkynyl‐2‐anilinopyrimidines properties 331–336 synthesis 751 herbicidal activity 331–336 biological activity 752–753 mode of action 336 chemical and physical resistance management 338 properties 750 site of action 336 chemistry 749–752 soil and environmental degradation and metabolism 757 behavior 336–338 and mechanism of 4‐amino‐3,5‐dichloropicolinate 320 resistance 754–757 4‐amino‐3,5‐dichloropicolinic mode of action 754–757 acid 319 structure–activity 4‐amino‐3‐isopropyl‐1,2,4‐triazol‐5‐ relationships 753–754 one 563 synthesis of 751 4‐amino‐6‐methyl‐4,5‐dihydro‐1,2,4‐ Anthonomus grandis 1024, 1303, 1465, triazin‐3(2H)‐one 1506 1510 3‐amino‐3‐methyl‐1‐pentyne 791 anthracnoses 689, 825, 881, 927, 970 aminomethyl phosphonic acid anthranilic diamide insecticides (AMPA) 455 chemical synthesis 1566–1567 4‐aminomethylpyrimidines 742 discovery of aminopyralid 321 chlorantraniliprole ® chemistry 322 (Rynaxypyr ) 1564–1565 discovery of 321–322 cyantraniliprole 1565–1566 herbicidal utility and insecticidal phthalic application 323–325 diamides 1563 mode of action 322–323 mode of action 1568–1571 amino‐pyrazolinones 835–836 anti‐Oomycete fungicides 871–877 4‐aminopyridine 734–738 Aonidiella aurantii 1058, 1060–1061 4‐aminopyridine, N‐(4‐pyridyl)biphenyl Aphis gossypii 1146, 1213, 1274, 1285, acetic acid amide 734 1298, 1323, 1336, 1368, 1372, aminopyrimidines 738–739 1517 aminoquinazolines 738–739 Apis mellifera 1172, 1236, 1344, 1379, aminoquinazolinones 1518

bindex.indd 1657 12/21/2018 3:11:04 PM 1658 Index

Aplysia californica (Ac‐AChBP) 1234 TIR1/AFB auxin receptors 306–310 acetylcholine‐binding protein 1288 weed selectivity 314 crystal structure of 1235 auxins, PGRs 573 appressoria formation 753, 938 avermectin aglycon derivatives 1490 Arabidopsis thaliana 19, 37, 44, avermectin B1 1482, 1485, 1490, 1491, 47–48, 50, 72, 101, 245, 266, 304, 1592 336, 351, 356, 388, 440, 478, 918 avermectins Arthropod Pesticide Resistance chemistry of 1481–1485 Database (APRD) 999–1000 structure 1482–1483 arylacetic acid amides 734–738, 740 AvictaTM 1586, 1591–1594 arylaminopyridines 718 azafenidin 179 aryl‐and hetarylurea 530 azimsulfuron 56, 73–75, 77 2‐aryl‐ cyclohexane‐1,3‐dione azolones 637, 665–667, 673 derivatives 517–519 azomethine anti‐feedant 2‐aryl‐cyclopentane‐1,3‐diones 511– pymetrozine 1509 517 azoxystrobin 579, 600, 601, 636, 641, 2‐aryl‐1,3‐dione (DEN) 501, 510 643, 644, 654, 655, 657, 659, 689, ArylexTM 311, 344–347, 433 1318 6‐arylpicolinates chemistry of 345 b discovery of 344–345 Bacillus firmus 1282, 1586, 1605–1606 herbicidal utility Bacillus thuringiensis 1010 ArylexTM 346–347 Bollgard 1111 RinskorTM 347–349 CAAS 1111 mode of action 345–346 CaMV 1108 aryl pyran‐and corn rootworms 1109 piperidine‐ Cry1A 1106 diones 520–524 crystal proteins 1104–1106 2‐aryl‐pyrazolo‐1,3‐diones 524–525 insect resistance to 1114–1115 2‐aryl‐pyridazine‐1,3‐diones 525 KMD 1113 arylsulfonyl acid amides 739–743 Leucinodes orbonalis 1112 2‐aryl‐tetramic acids 519–520 Manduca sexta 1106–1107 2‐aryl‐tetronic acids 519–520 Ostrinia nubilalis 1108–1109 ATP synthase 624–627, 703, 707, pest control of 1110 1137, 1138, 1140, 1141 plant engineering 1103–1104 atractyloside 627, 628 resistance management 1115 auxin‐binding protein 1 (ABP1) 311 tobacco plants 1107 auxin herbicides Bactrocera cucurbitae 1466 ABP1 311–312 Bactrocera dorsalis 1402, 1466 auxin transporters 312–314 Baermann funnels 1649 binding studies 311 Basic Local Alignment Search Tool effects of treatment 305 (BLAST) 876, 881 field resistance 314–315 Basidiomycetes 458, 599, 603, 623, indole‐3‐acetic acid (IAA) 303 635, 666, 688, 689, 696–698, 785, in vitro binding assays 309 797, 798, 801, 836, 1174 3 3 molecular MOA 303 [ H]batrachotoxin‐B ([ H] perception and signaling 305–306 BTX‐B) 1435

bindex.indd 1658 12/21/2018 3:11:04 PM Index 1659

® Battalion 431 1,2,4‐benzotriazine‐1‐oxides 923 β‐carotene 214, 216, 217, 243 benzovindiflupyr 684, 688–689 β‐chitin 1068 benzoyl cyclohexane‐1,3‐dione (CHD) β ‐diketones 749 herbicides 242 beflubutamid 232, 234, 237, 238 benzoylphenyl ureas (BPUs) Bemisia tabaci 1056–1060, 1074, bistrifluron 1074 1205, 1252, 1275, 1323, 1336, chlorfluazuron 1071 1369, 1375, 1377, 1509, 1510 diflubenzuron 1071 bencarbazone 201 flucycloxuron 1074 benodanil 681 flufenoxuron 1073 benoxacor 274, 278, 429–431, 443 hexaflumuron 1073 benthiavalicarb 845–847, 852–854, 863 lufenuron 1073–1074 benzamide fungicide 588, 701, 786, 1630 NK‐17 1074 benzamide nematicides novaluron 1073 mitochondrial complex II inhibitors noviflumuron 1073 fluopyram mode of synthetic routes 1071–1072 action 1633–1634 teflubenzuron 1072 flutolanil inhibition 1634–1635 benzyl uracils 192 pyridinyl‐ethyl benzamide best management practices fluopyram 1630 (BMPs) 10, 465–467 structure and function 1631–1633 β‐1,4‐glucan accumulation 409 plant‐parasitic nematodes β‐1,4‐glucan chains 391 cucumber 1638 β‐1,3‐glucan synthetases 954 in fruiting vegetables 1638 bicyclopyrone 244, 254, 266, 268, 272, Meloidogyne spp. 1637 273, 278–280, 430, 433 methodology 1637 bifenazate in potatoes 1640 ecobiology 1188 in tobacco 1641 physiochemical data 1187 tomatoes 1638–1640 registration status 1188–1189 benzenedicarboxamides 1541, resistance behavior 1189 1549–1551, 1553, 1560 structure activity 1183–1187 benzfendizone 184–186, 188 structure of 1184 benzimidazoles 189, 190, 589, 592, binapacryl 707, 710, 715 594–596, 599, 600, 706, 707, 709, bionematicide, VotivoTM 1605–1606 773, 774, 798, 915, 927, 934 biotin carboxy carrier protein benzobicyclon 254, 261, 271, (BCCP) 16 276–278, 367 biotin carboxylase (BC) 16, 502 benzofenap 291–293, 297, 301 bisacylhydrazine (BAH) 1013 benzoheteroaryl Protox herbicides 190 commercial activity of benzoheterocycles 176, 188–190, 198 chromafenozide 1034 benzoheterocyclic to fufenozide 1034 heterocycle 188–192 halofenozide 1034–1038 benzonitriles methoxyfenozide 1033, biological activity 394–395 1038–1039 chemistry of 392–393 tebufenozide 1033 benzo[1,2,3]thiadiazole‐7‐carboxylic discovery and structures of acid 965 1016

bindex.indd 1659 12/21/2018 3:11:04 PM 1660 Index

bisacylhydrazine (BAH) (contd.) bongkrekic acid 628 20E 1028 Borrelia burgdorferi 1467 ecdysone agonist 1044 boscalid 600, 685–688, 690, 699, 700, ecdysteroids 1024 1602 EcR 1024, 1025 Brevipalpus phoenicis 1093 insect molting hormone 1014–1016 bromethalin 706, 718 LBD 1025 2‐bromoacetophenone 291, 293 lethal effects 1029–1030 bromuconazole 819–820 mammalian, ecotoxicology brood compensation index data 1041 (BCI) 1346 mode of action brood termination rate (BTR) 1346 insect toxicity of 1031–1033 β‐tubulin 786–787, 789, 792 lethal effects 1029–1030 Bulinus truncatus (Bt‐AChBP) 1234 sub‐lethal effects 1030–1031 buprofezin 1074, 1075, 1549 resistance mechanisms and butafenacil 184, 185, 202, 204 potential 1043–1044 butenolides structure–activity relationship discovery of 1362–1365 (SAR) 1019–1022 insect vs. vertebrate 1249 sub‐lethal effects 1030–1031 MoA insects 1244 synthesis of 1017–1019 bis‐aromatic alkynes 399 c bispyribac‐sodium 135–137 Caenorhabditis elegans 1230, 1456, bistrifluron 1072, 1074 1481, 1593, 1625, 1632, 1648 ® bitertanol 812, 1299 Calaris 271, 274 bixafen 601, 683, 689, 1602 calcium‐induced calcium release Blattella germanica 1070, 1457 (CICR) 1542 ® bleaching herbicides CAMIX 275 biology and use pattern 233–234 Capitella teleta (Ct‐AChBP) 1234 ® carotenogenic pathway 219 Capreno 152, 164, 165, 275, 436 carotenoid biosynthesis carbamates 231, 374, 404, 410, 411, in higher plants 215–217 592, 645, 850, 854, 856, 989, HPPD inhibition 214 1010, 1051, 1518, 1588 plastoquinone 213 carbamoyl isoxazoles 642 plastoquinone properties and carbamoyl tetrazolinones 363, function 214–215 367–369 genetic engineering 219 carbazate acaricide 1183–1185 lycopene cyclase (LCC) 217–218, 454 definitions of 1185 phytoene desaturase and ζ‐carotene formula of 1184 desaturase 217 carbendazim 600, 785, 788, 789 phytoene desaturase carboxamides 327, 367, 589, 696, 896, inhibitors 234–237 1174, 1175, 1426 (E)‐β‐methoxyacrylates (MOAs) 638 carboxin 599, 623, 681, 690, 700, 1174 Bollgard II 1111 carboxylic acid amide (CAA) 592, 603, Bombus terrestris 1039, 1344, 1345, 740, 793, 845–866 1416, 1522, 1536 amino acid amides Bombyx mori 1055, 1179, 1237, 1518, aminosulfones 854–856 1538, 1546 benthiavalicarb 852–853

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iprovalicarb 850–852 cobtortin 412 N‐sulfonyl amino acid commercialized inhibitors, properties amides 856 of 413 valifenalate 853–854 coumarins 411–412 biological activity 862–863 epopromycins 416 cinnamic acid amides in higher plants 387 dimethomorph 847–848 inthomycins 415–416 flumorph 848–849 N‐Aryl Lactams 410–411 pyrimorph 849 plant‐conserved region (PCR) 389 glyoxylic acid derivatives 860–862 primary and secondary cell mammalian toxicology of 847 walls 388 mandelic acid amides, sangivamycin 416–417 mandipropamid 856–863 thaxtomins 413–415 mode of action and mechanism of thiatriazines 407–410 resistance 863–866 triazolocarboxamides 401–403 carboxyltransferase (CT) 16, 502, uridine diphosphate (UDP) 389 1216–1218 cellulose biosynthesis inhibitors carfentrazone-ethyl 178 (CBIs) 4, 387, 392 carotenes 215–216 cellulose microfibrils 391, 392, 412 carotenoid biosynthesis cellulose synthase complex (CSC) 388 in higher plants 215 cellulose synthase interacting protein 1 HPPD inhibition 214 (CSI1/POM2) 392 plastoquinone 213 central nervous system (CNS) 706, properties and function 214–215 993, 1223, 1253, 1255, 1373, carotenoids synthesis 243 1374, 1433, 1434, 1450 carpropamid 603, 882, 885, 889, cereals 62 894–897, 899, 1299, 1305 flupyrsulfuron‐methyl‐ catalytic subunits (CSU) 36, 617 sodium 64–65 cauliflower mosaic virus iodosulfuron‐methyl‐sodium 66–67 (CaMV) 1108 mesosulfuron‐methyl 67–69 CCMT, synthetic pathways 1278 methiopyrsulfuron 71 cellulose biosynthesis monosulfuron 71 accessory proteins 392 safener mefenpyr‐diethyl 67 acetamides 398–399 sulfonylurea herbicides 63 alkylazines 403–407 sulfosulfuron (MON 37500) 65–66 benzamides 395–398 tritosulfuron 69–71 benzonitriles Cestrin 412–413 biological activity 394–395 C15 farnesyl pyrophosphate chemistry of 392–393 (FPP) 215 bis‐aromatic alkynes 399–401 C17‐forosamine 1407 β‐1,4‐linked glucan chain 391 CGA 293’343 1317–1331 cellulose microfibrils 391 CGA 325615 407, 409, 410 cellulose synthase complex C20 geranylgeranyl pyrophosphate (CSC) 388 (GGPP) 215 CesA proteins 389–390 channel‐blocking insecticides CESTRIN 412–413 semicarbazone sodium 1426 class‐specific region (CSR) 389 Chelacaropsis moorei 1529

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chemical uncouplers 629, chlorophyll biosynthetic 710–714 pathway 174–175 chemiosmotic hypothesis 610 chloroplastic isoform (GS2) 477 Chilo suppressalis 1016, 1071, 1113, 2‐chloro‐1,3‐thiazol‐5‐ylmethyl 1574 (CTM) 1276 chitin biosynthesis 2‐chlorothiazol‐5‐ylmethyl 1387 action mechanism 1069–1070 2‐chloro‐6‐ CHS 1068–1069 trichlormethylpyridine 234 cuticular exoskeleton 1067 3‐chloro‐5‐trifluoromethyl‐2‐pyridinyl inhibitors residue 695, 696, 698 BPU 1071 chlorthiamid 393 buprofezin 1074 chordotonal organ TRPV channel cyromazine 1075 modulators 1502 polyoxin D 1071 Choristoneura fumiferana 1025, 1032, chitin synthase (CHS) 1068–1069, 1035 1086, 1090, 1094 chromafenozide 1016, 1019–1020, Chlamydomonas 244, 245, 253 1023, 1031, 1033, 1034 chlorfenapyr 1150, 1152 Chrysoperla carnea 1121, 1273, 1357, ® chlorantraniliprole (Rynaxypyr ) 1536, 1559 ® biological profile Cinch 430 insecticidal potency and cinidon‐ethyl 180–181 attributes 1571–1573 cinnamic acid amides IRM method 1574–1575 dimethomorph 847–848 mammalian and environmental flumorph 848–849 safety 1573 pyrimorph 849 mechanisms of resistance, 14C‐iprovalicarb 863 ® diamides 1575–1577 Ciral 64 discovery of 1564–1565 9‐cis‐epoxycarotenoid dioxygenases chlorfenapyr 663, 707, 1146, (NCEDs) 305 1150–1154, 1467 ClarivaTM 1586, 1605, 1606 chlorfluazuron 1071, 1072, 1074 clofentezine 1086–1091 chloride channel 1592 clopyralid 163, 274, 304, 315, 318–322, chloroacetamides 234, 354, 357–359, 324, 325 363, 443–444 cloquintocet‐mexyl 432–434 3‐chloro‐1,2‐benzisoxazole‐1,1‐ cloransulam‐methyl dioxide 964 crop selectivity 110–111 2‐chlorobenzothiazole 365 crop utility 109–110 chlorocarbonyl triazolinone 561 environmental degradation, 6‐chloro‐3‐chloromethyl‐pyridine ecotoxicology, and (CCMP) 1296 toxicology 111–112 chloro‐dinitrobenzene (CDNB) 23 clothianidin 1276, 1279, 1281, 1317 (5‐chloro‐6‐ethylpyrimidin‐4‐yl)(1‐ chemical classification 1276–1277 naphthaleno‐2‐ylethyl) physicochemical properties of 1277 amine 732 spectrum activity 1280 chloronicotyinyl insecticides Cnaphalocrocis medinalis 1113, 1464, (CNIs) 885 1563 4‐chloro‐2‐pentenamides 192 COBRA‐like proteins 392

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cobtorin 412 1‐cyclopropyl‐butane‐1,3‐dione 749 colchicine 787, 789 cyclosulfamuron 56, 57, 75–79 comparative molecular field analysis Cydia pomonella 1058, 1303–1304, (CoMFA) 1021, 1286, 1297 1331, 1337, 1338, 1413, 1415 complex I inhibition cyenopyrafen 1168–1171 aminoalkylpyrimidines cyflufenamid diflumetorim 729 cross resistance 934–935 structure–activity relationship discovery 933–934 (SAR) 731 manufacturing process 935–936 structure of class 729 and mode of action 934–935 arylacetic acid amides 734–738 cyflumetofen 1171 arylsulfonyl acid amides 739–743 development stages 1172 insecticides and acaricides 727 ecobiology 1172 phenoxan 743 registration status 1173 phenylacetic acid amides 738–739 resistance behavior 1173 Conyza canadensis 24, 278, 464 structure of 1171 Coptotermes formosanus 1074, 1466 synthesis of 1172 Cosmopolites sordidus 1464 cymoxanil cotton herbicide 134–135 chemical structure 912 coumarins 411–412, 708 commercial usage 912 coumoxystrobin 645 host–pathogen interactions 915 crop baiting system 1465–1466 market significance 913 cross‐resistance 14, 16, 17, 19, 1000 physico‐chemical properties 912 metaflumizone 1447 preventative/curative spinosyns 1406 application 915 sulfoxaflor 1348, 1349 sporulation‐inhibiting crystal protein (Cry) proteins properties 913 Bt insecticides 1104 synthesis 913 structures of 1106 CYP6CM1vQ 1286, 1376–1378, Ctenocephalides felis 1252, 1467, 1382 1481 cyprodinil 602, 728, 749–750, Curcurbit Yellow Stunting Disorder 752–756, 774, 934 Virus (CYSDV) 1376 cyprosulfamide 152, 157, 164, 167, Curvularia spp. 839, 1280 293, 427, 437, 438 cuticular exoskeleton 1067 cyrmenins 638 cyanohydroxyiminoacetamides 911 cyromazine 1075 3‐cyanopyrroles 769 Cys‐loop receptor (CLR) 1233, 1455 cyantraniliprole (Cyazypyr®) 327, cystathionine‐β‐lyase (CBL) 755 1565–1566 cyst nematode 1282, 1585, 1594, 1600, biological profile 1577 1606, 1615, 1636, 1651 discovery of 1565 cytochrome‐P450‐dependent mono‐ cyazofamid 634, 636, 665–667, 670, 673 oxygenases 1509 cyclic ADP‐ribose (cADPR) 1543 cytochrome‐P450 monooxygenase cyclization reactions 216, 965, 1302, system 21 1315, 1316 cytokinins, PGRs 574 cyclohexanediones (CHDs) 16, 253, cytoplasmic male sterility (CMS) 457 258, 259, 262, 287, 501, 508–510 cytosolic isoform (GS1) 477

bindex.indd 1663 12/21/2018 3:11:04 PM 1664 Index

d benoxacor 429–430 Daminocide 577 dichlormid 431 Danaus plexippus 1120 2,6‐dichlorobenzonitrile 392 Daphnia magna 542, 1347, 1492, diclomezine 1494 chemical structure 921 DCJW 1432–1436, 1447 and ecotoxicological profile 923 Delia coarctata 1465 physico‐chemical properties 922 demethylation inhibitors (DMIs) 574, rice sheath blight 922 592, 664, 798 synthesis of 921 density functional theory (DFT) 893, toxicological 923 1287, 1362, 1363 diclosulam 1‐deoxy‐D‐xylulose‐5‐phosphate crop selectivity 110 (DOXP) 215 crop utility 109–110 Dermatophagoides farinae 1528 ecotoxicology 111–112 d‐glufosinate 488 environmental diafenthiuron degradation 111–112 acute toxicity 1139 metabolism of 110 biological activity 1144–1146 and toxicology 111–112 crop protection 1144–1146 dicyclomet 882 mode of action 1139–1141 dieldrin 1452–1454 structure–activity relationship diethofencarb 599, 600, 788, 789, 792 ® (SAR) 1142 DiFlexx 437 toxicology and ecotoxicology 1144 diflovidazin 1086–1094 diamide‐resistant P. xylostella 1575 diflubenzuron 1069–1071, 1075, diamides insecticides 1076 anthranilic 1562 diflufenican 67, 218, 222, 233, 365 binding site and target‐site diflumetorim 728–730, 734, 738, resistance 1545 1175 chemical structures 1541–1542 1,4‐dihydro‐1‐phenyl‐5H‐tetrazol‐5‐ mode of action 1543–1545 thiones 1143 diarylamines 708, 710, 717–719 dihydropicrotoxinin 1451, 1452 diaryl‐tetrazines 1087 dihydropyrazoles 1433–1437 dicamba 25, 152, 163, 166, 167, 274, 1,8‐dihydroxynaphthalene (DHN) 308, 456, 459–462, 468, 469, melanin 879 472, 473 biosynthetic pathway 879–881 dicamba resistant (DR) trait carpropamid 896–897 DMO transformation, in fungicidal activity 881 soybean 461–462 heavy metals 881 field evaluation, stacked polyketide synthase (PKS) 882, 883 soybeans 462–464 scytalone dehydratase (SD) 886 identification 459–461 computational investigations, of dicarboximides 761–766 enzyme mechanism 891–893 dichlobenil 392–395, 402, 407, 411 and inhibitor structures 893–896 dichlormid 429, 431, 443 site‐directed mutations 896 dichloroacetamide 443 X‐ray structures and active dichloroacetamide safeners site 889–891

bindex.indd 1664 12/21/2018 3:11:04 PM Index 1665

1,3,6,8‐tetrahydroxynaphthalene Drosophila α‐subunit (SAD) 1252 reductase 885 Drosophila Kc cells 1016, 1023 ® tolprocarb Dual‐II‐magnum 430 biological activity 902–904 Dysdercus cingulatus 1463 inhibiting PKS activity 898–900 structure–activity e relationships 900–902 ecdysone agonist, BAH 1044 3,4‐dihydroxyphenylalanine L‐ ecdysone receptor (EcR) 1013, 1021, (DOPA) 879 1024 dihydroxyxanthenone formation 258 ligand binding domain (LBD) 1025 diketonitrile (DKN) 244, 286, 294, ecdysteroids 1013, 1016, 1019, 1021, 295 1024, 1025, 1027, 1028 dimefluazole 667 Echinochloa spp. 13, 81, 82, 115, dimethomorph 793, 845, 847, 855, 137–139, 147, 367, 382, 494 862–864, 871 E. crus‐galli 73, 109, 115, 117, 134, 1,3‐dimethyl‐5‐pyrazolon 289, 290, 298 166, 364, 376, 401 ® Dinamic 564 E. oryzicola 137–139, 145, 276, 380 dinitrocresol (DNOC) 706 ecotoxicology 542–544, 547, 872–873, dinitrophenols 706, 708, 715, 718, 985–986, 1144 1156 emamectin dinobuton 715 benzoate 1146, 1478, 1480, 1482, dinocap 706, 707, 715 1491, 1492, 1495, 1496, 1544, dinotefuran 1282, 1284 1554, 1557 chemical classification mites and insects 1491 of 1282–1283 synthesis of 1484 physico‐chemical properties 1283 endo‐/sarcoplasmic reticulum (ER/ spectrum activity 1285 SR) 1541 diones 259, 262 enestroburin 635, 645 dioxapyrrolomycin 1149, 1150 5‐enolpyruvylshikimate‐3‐phosphate diphenylalkanoylaminopyridines 734 synthase (EPSPS) 338, 454, diphenyl ether herbicides 176 532 diphenyl‐oxazolines 1097 glyphosate 20 ® 4,6‐disubstituted pyrimidines 750 Envidor , ACCase 1211–1212 dithiopyr environmental toxicology biology 494 aquatic nontarget species 1347 synthesis 497–499 terrestrial nontarget dorsal unpaired median (DUM) 1433, species 1343–1347 1456 Ephestia kuehniella 1121 D1 protein 15, 214, 244 epopromycins 416 DPX‐JW062 1427 epoxiconazole 579, 816–819 drazoxolon 716 ergosterol biosynthesis 797, 799–801, Drosophila 833 D. melanogaster 1024, 1025, 1070, Erwinia chrysanthemi 1233 1237, 1347, 1350, 1405, 1453, ethaboxam 600, 786, 788, 791, 792 1481, 1544, 1568, 1648 ethoxysulfuron 56, 73, 75–76, 436 nAChR subunits 1231, 1232 ethylene, PGRs 573

bindex.indd 1665 12/21/2018 3:11:04 PM 1666 Index

ethyl 2‐(4‐fluoro‐3‐ fenpiclonil 764 trifluormethylphenoxy) chemical and physical butanoate 238 properties 770, 771 etoxazole 1085–1101 Knoevenagel condensation 769 European and Mediterranean Plant production processes 769 Protection Organisation synthesis 769 (EPPO) 542 fenpyrazamine 602, 835–839 fenpyroximate 614, 663, 1141, f 1163–1164 fatty acid synthase (FAS) fentrazamide 148, 271, 272, 276, 357, inhibitor 353, 503, 882 358, 363, 365–371 feeding blockers ferimzone 715–717 biological activity and use fipronil recommendations of 1517 chemical and physical properties flonicamid of 1460, 1598–1599 biological mode of action 1516 degradation of 1469 discovery of 1512 flavin adenine dinucleotide (FAD) 33, resistance 1517 36, 609, 621, 1632 synthesis of 1512–1516 subunit structure 37, 38 ® IRAC 1502 Flexity 939 pymetrozine flonicamid 1501–1502 chemical and physical properties aphicidal spectrum of 1517 of 1506 biological mode of action 1516 discovery 1502–1505 chemical and physical properties pyridine azomethines 1506 of 1516 synthesis 1506 resistance 1517 pyrifluquinazon safety profile 1518 chemical and physical properties synthesis of 1512–1516 of 1521 target sites 1516–1517 discovery of 1518–1519 florasulam synthesis of 1520–1521 crop selectivity 110–111 fenamistrobin 635, 645 crop utility 110 fenazaquin 663, 727, 743, 1138, 1163, ecotoxicology, and toxicology 112 1165–1166, 1192, 1194 environmental degradation 112 fenbuconazole 814–816 metabolism of 111 fenclorim 444 fluacrypyrim 635, 663, 1175, 1182, fenfuram 681, 685 1192, 1195 fenhexamid 595, 602, 604, 833–837, fluazaindolizine 1586, 1603–1604, 1643 839 biological profile 1649–1652 fenoxanil 882, 885, 886, 894–896 chemical nomenclature 1646 fenoxaprop‐p‐ethyl 435 classification 1646 fenoxasulfone ecotoxicological profile 1646, 1648 biological activities 381–382 mode of action 1647–1649 chemistry 380–381 nematicidal symptoms 1647–1649 commercial products 382 N‐phenylsulfonylimidazopyridine‐2‐ mode of action 383 carboxamide lead physicochemical properties 382 compound 1644

bindex.indd 1666 12/21/2018 3:11:04 PM Index 1667

physical‐chemical properties 1646 flufenoxuron 1073, 1544, 1554, 1556 RKN 1645 flufenpyr‐ethyl 184–186 structure of 1644–1646 flumetsulam 18, 19, 107, 123 toxicological endpoints 1646–1647 flumiclorac‐pentyl 180, 181 fluazinam 706–708, 718–719 flumorph 845, 848–849, 864 fluazolate 179, 195, 197 fluopicolide 695 flubendiamide chemical and physical chemistry properties 871–872 beneficial arthropods 1558 P. infestans, effect on zoospores and 1,2‐benzendicarboxamide mycelial growth of 873–874 derivatives 1551 spectrin‐like protein cross‐resistance 1558 distribution 874–877 fast‐acting activity 1554–1558 in P. infestans by lepidopterous pests 1554 bioanalysis 876–877 persistence 1554 toxicology/ecotoxicology 872–873 structure–activity relationship fluopyram 689, 694–701, 1299, 1586, (SAR) 1553 1602–1603, 1630–1642 toxicological profile 1558–1559 fluopyram SC400 ® X‐ray structural analysis 1553 (Velum ) 1636–1641 history of invention 1549–1550 fluoroalkenyl nematicides flucarbazone‐sodium 151, 153, 162 1597–1598 flucetosulfuron 56, 57, 78–80 fluoxastrobin 643, 652, 655, 657, 659, fludioxonil 671, 827, 828, 925 biokinetic data, for grape berries flupoxam 392, 401–403 treatment 773 flupropacil 184, 185 biological mode of action 776 flupyradifurone chemical and physical biological profile of 1374–1375 properties 770, 771 CYP6CM1vQ 1377–1378 in vitro activity spectrum 771, 772 discovery of 1365–1370 production processes 769 laboratory synthesis 1366 seed‐treatment purposes 775 physico‐chemical synthesis 770 properties 1369–1370 fluensulfone (NimitzTM) structure–activity relationship biological lab and field (SAR) 1368–1369 activity 1600 honey and bumble‐bees chemical and physical safety 1379–1381 properties 1598–1599 mammalian safety discovery 1594–1597 profile 1378–1379 ecotoxicity profile 1601–1602 mode of action 1373–1374 fluoroalkenyl group 1594 nontarget arthropods 1379 mode of action 1599–1600 physicochemical properties 1370 safety profile 1601–1602 plant uptake and structure–activity profile 1597–1598 translocation 1370–1373 synthesis of 1598 speed of action, feeding use recommendation 1600–1601 cessation 1372–1373 flufenacet 293, 355, 356, 360, 363–366, synthetic pathways 1366 371 virus vector control 1376

bindex.indd 1667 12/21/2018 3:11:04 PM 1668 Index

flupyrsulfuron‐methyl‐sodium fungal respiration 601 (DPX‐KE459) 64 Fungicide Resistance Action fluquinconazole 753, 824–825 Committee (FRAC) 596 flurazole 430, 442–443 global market 592–593 fluridone 225–227, 233–234, 237, 243 history of usage 589–590 flurochloridone 226, 233–234, 237 host plant defence induction 605 flurtamone 223, 225–227, 233, 234, lipid synthesis and membrane 237 integrity 603 flusulfamide mechanisms and chemical structure 919 occurrence 593–595 market significance 920 melanin synthesis, in cell wall 605 physico‐chemical mode of action 590–593, 598–607 properties 919–920 multisite mode of action 607 synthesis scheme 920 nucleic acid synthesis 599 flutenzine 1086–1091 practical resistance, occurrence flutianil 933, 943–945 of 594 flutolanil 623, 685, 696, 1174, 1176, resistance management and risk 1630, 1634–1635 modifiers 597–598 fluxapyroxad 689, 699, 1602 resistance risk assessment 597 fluxofenim 430, 432, 433, 442–443 signal transduction 602 ® Folicur 813 sterol biosynthesis 604 foramsulfuron 56, 58, 82–84, 436, 446, Fungicide Resistance Action Committee 534 (FRAC) 587, 590, 596, 664, 756, fosetyl‐aluminum 778, 787, 802, 845, 938, 955, 959, chemical structure 915 996 foliar application 916 classification 802 gene‐expression changes 918 furametpyr 685, 690, 691, 1176 glucose metabolism 918 furilazole 429, 431, 432 physicochemical properties 916 Fusarium spp. 590, 599, 601, 716, 743, toxicological profile 917 771, 774, 775, 820, 821, 828, Frankliniella spp. 1297, 1464–1465 1119, 1642 F. occidentalis 1219, 1405, 1492, F. moniliforme Sheld 574 1494, 1535 fthalide 882, 885 g fufenozide 1016, 1019, 1021, 1034 GABA‐gated cation channel 1230, 1456 4‐fumarylacetoacetate lyase 243 insect GABA receptor fumigant nematicides 1587–1588 cloning 1453–1454 fungicide γ‐aminobutyric acid (GABA) 993, amino acid and protein 1189, 1389, 1450, 1481, 1592 synthesis 602 biological properties cell wall biosynthesis 604 biological spectrum 1463–1464 classification 598–607 crop baiting system 1465–1466 cytoskeleton and motor foliar applications 1465 proteins 600 seed treatment 1464–1465 with FRAC serial number and soil applications 1464 unknown mode of action 606 chemistry

bindex.indd 1668 12/21/2018 3:11:04 PM Index 1669

structure–activity herbicidal symptoms 482 relationship 1461–1463 herbicide resistance 488 synthesis of fiproles 1458–1461 N‐acetyl‐ ethiprole 1450 phosphinothricin 487–488 fiprole insecticides 1449 physiological effects fipronil 1449–1450 482–483 mode of action 1450–1458 uptake and translocation, of receptor, insecticide target glufosinate‐ site 1451–1453 ammonium 483–484 resistance and L‐phosphinothricin 476, 481 management 1467–1468 phosphinothricin 479–480 γ‐chitin 1068 plant nitrogen gene expression 353, 355, 379, 438, metabolism 477–479 440, 441, 685, 762, 877, 918, 961, tabtoximine‐β‐lactam 476 962, 969–975, 1045, 1104, 1212 glutathione (GSH) 21, 23, 439, gibberellins, PGRs 573–574 443–445, 915 Global Diamide Working Group glutathione S‐transferase (GST) 360, (WG) 1574 438–440, 444, 446, 967, 1025, Gloeobacter violaceus 1233 1173, 1576 glufosinate 164, 451, 452, 454, 456, metabolic detoxification 21–24 463, 472, 473, 477, 482–488 glycine‐gated chloride channels 1457 glutamate‐gated chloride channels glyoxylic acid derivatives 845, (GluCls) 993, 1230, 1400, 1450, 860–862 1454, 1456–1457, 1478–1497, glyphosate 5, 7, 10, 13, 14, 20, 24–26, 1592, 1648 47, 50, 51, 84, 164, 174, 203, 245, agriculture, use in 1495–1497 278, 331, 334, 347, 451–473, 484, allosteric modulators 1478, 1481 487, 1110 avermectins, chemistry N‐phosphonomethyl glycine 454 of 1481–1485 glyphosate‐resistant 13, 20 market products Golden Crownbread (Verbesina names and codes 1479 encelioides) 325 properties 1480 green chemistry 1041, 1283, 1402, milbemycins, chemistry 1404, 1419, 1552 of 1485–1488 growth inhibitors, PGRs 574 mode of action 1480–1481 safety h and bioavailability 1492–1494 halofenozide 1016, 1017, 1022–1024, and environment 1495 1028, 1029, 1032–1038 glutamine synthetase (GS) Harmonia axyridis 1179, 1353, 1357, inhibitors 532 1518, 1536, 1559 herbicidal activity, of haustoria formation 753, 938, 954 phosphinothricin Helicoverpa spp. 1414, 1531 in agriculture and H. armigera 997, 1036, 1105, 1154, horticulture 484 1298, 1437, 1496, 1535, 1555 crop selectivity 484–487 H. zea 1036, 1106, 1294, 1481, environmental conditions 483 1496

bindex.indd 1669 12/21/2018 3:11:04 PM 1670 Index

Heliothis virescens 1021, 1026, 1036, field evaluation, stacked 1105, 1106, 1111, 1115, 1117, soybeans 462–464 1119, 1149, 1244, 1251–1253, identification 459–461 1255, 1298, 1322, 1361, 1409, disease control benefits 458–459 1447, 1459, 1488, 1496, 1535, field performance, of weed control 1544, 1568, 1570 systems 470–472 Heliothis virescens ecdysone receptor glyphosate resistant (GR) trait (HvEcR) 1027, 1028 AMPA 455 LBD 1021, 1022, 1028 development of 455–456 herbicide resistance (HR) 488 EPSPS 454–455 definition 10 integrated weed management multiple resistance mechanisms 25–27 (IWM) 465–467 nontarget‐site mechanisms mechanism 451–452 enhanced metabolic metribuzin 469–470 detoxification 21–24 roundup hybridization herbicide distribution 24–25 system 456–458 ® population evolution 10–14 Roundup Ready Plus (RRP) target‐site mechanisms Program 467 ACCase inhibitors 15–18 weed resistance 464–465 ALS/AHAS inhibitors 18–20 heteroarylmethylamines 739–473 EPSPS 20 Heterotermes tenuis 1464 PPO 20–21 hexaflumuron 1073, 1074 PS II inhibitors 15 hexythiazox 1091–1094 weed control field applications 1096 agricultural regions 5–6 synthetic pathways 1095 chronological increases 5, 7 HGA phytyltransferase (HPT) 243, 244 weed survey 5–28 HGA solanesyltranferase (HST) 243 Herbicide Resistance Action Committee Hill reaction 126, 406, 530 (HRAC) 359 histamine‐gated chloride classification scheme 529 channel 1230, 1455, 1457 classification system 7–10 histidine kinases 761–764 members, organization and Hordeum leporinum 24 tasks 27–28 host defense inducers missions and goals 27 genetically modified (GM) multiple resistance crops 960 mechanisms 25–27 induced resistance non target‐site resistance biochemical changes 962 mechanisms 21–24 endogenous phytohormones 960 population evolution, IWM 10–14 priming 963 target‐site resistance signal perception and mechanisms 14–21 transduction 962 herbicide resistant (HR) crops systemic acquired resistance 961 best management practices market products (BMPs) 465–467 acibenzolar‐S‐methyl 964–967 dicamba resistant (DR) trait isotianil 967–975 DMO transformation, in probenazole 963–964 soybeans 461–462 tiadinil 967

bindex.indd 1670 12/21/2018 3:11:04 PM Index 1671

house dust mites 1527–1529 i 5‐HT3 (serotonin type 3) imazamethabenz methyl 97, 98, 102, receptors 1455 103 ® Hussar 67, 435 imazamox 99, 101–103 hydramethylnon 1183 imazapic 99, 101–103, 441, 442 1,4‐hydroxyanilide fungicides 834 imazapyr 18, 41, 98–103, 128, 140, hydroxyanilides 833–836 141 20‐hydroxyecdysone (20E) 1013 imazaquin 19, 44, 45, 50, 98, 99, 102, BAH 1028–1029 103 chemical structures of 1014 imazethapyr 46, 99–103 insect molting imibenconazole 825–826 hormone 1014–1016 imidacloprid (IMI) 1241, 1293, 1350, hydroxyethyl‐ThDP (HEThDP) 1389 AHAS 34 biological activities of 1284 binding site AHAS 41 chemical classification 1295–1296 2‐(4‐hydroxy‐3‐methoxy) homoptera pest insects 1298 phenethylamine 857 lepidoptera pest insects 1298 2‐hydroxy‐[N‐(4‐fluorophenyl)‐N‐ physicochemical isopropyl] acetamide 365 properties 1295–1296 2‐hydroxy‐[N‐(methyl)‐N‐phenyl] synthetic pathways 1294 acetamide 365 imidazoles 402, 670, 803, 806–812, 4‐hydroxyphenyl‐pyruvate 214 889, 1462, 1482, 1502 hydroxyphenylpyruvate dioxygenase 2,4,5‐imidazolidinetriones 197 (HPPD) imidazolinone herbicides in Arabidopsis 241, 243, 244 commercial uses of 103–104 benzoyl cyclohexane‐1,3‐dione history of 96–98 (CHD) herbicides 241 metabolism of 102–103 carotenoids synthesis 243 mode of action 100 heterocycles physico‐chemical properties 98 benzofenap 291–293 structural features of 98–100 isoxaflutole (IFT) 293–295 structure of 95–96 pyrasulfotole 297–298 synthesis method 96 pyrazolynate tolerant crops 101–102 (pyrazolate) 288–290 imidazolinone‐tolerant crops pyrazoxyfen 290–291 101–102 tolpyralate 298–299 indaziflam 392, 404, 405, 407, 413, topramezone 296–297 414 inhibition 248–250 indole‐3‐acetic acid 303, 318 photosynthetic organisms 242 indole‐acetic acid (IAA) 336, 573 PQ 242–243 indoxacarb selectivity 244–245 DCJW 1433–1435 structure and mechanism 245–247 and dihydropyrazoles 1433–1435 tyrosine degradation pathway 242, discovery of 1427–1429 243 insecticidal activity 1429–1431 4‐hydroxyphenylpyruvate dioxygenase mammalian vgSCs 1435–1436 (HPPD) 3, 164, 214, 255, 365 mode of action hyperecdysonism 1029 and dihydropyrazoles 1433–1435

bindex.indd 1671 12/21/2018 3:11:04 PM 1672 Index

indoxacarb (contd.) programs 1574–1575 mammalian vgSCs 1435–1436 strategies 1009–1010 proinsecticide action 1432–1433 virus vector control 1376 physico‐chemical properties 1430 insecticide resistance, progression product 1430 of 995–996 proinsecticide action 1432–1433 insect molting hormone resistance 1436–1437 BAH 1013 vgSCs 1431–1432 20E 1013, 1014 inositol hexaphosphate (IP6) 306 insect vs. vertebrate inositol 1,4,5‐trisphosphate receptor butenolides 1249 (IP3 receptor/IP3R) 1541 mesoionic insecticides 1249 insect growth regulator (IGR) 544, neonicotinoids 1247–1248 1049, 1053, 1073, 1074, 1156, spinosyns 1244, 1248 1303, 1346, 1436, 1574 sulfoximines 1248 Insecticide Resistance Action integrated pest management Committee (IRAC) 1468, 1501 (IPM) 1090, 1501, 1530, 1646 ® acaricide pyflubumide 1180–1181 Envidor 1211–1212 ® action classification of 1002 Oberon 1211–1212 activities integrated weed management APRD 999–1000 (IWM) 10, 13–14, 338, education and 465–467 communication 999 International Survey of herbicide‐ MSU 999–1000 resistant weeds 5, 26, 27 resistance management inthomycins 415–416 regulatory 998–999 invertebrate γ‐aminobutyric resistance‐monitoring acid 1481 methods 998 iodosulfuron‐methyl‐sodium (AE compound rules 1001–1008 F115008) 56, 63, 66–69, 82–84, Global Diamide Working Group 435, 441, 446 (WG) 1574 ionophores 704, 1070 IRM strategies 1009–1010 ionotropic GABA receptor 1455 market trends 1010–1011 ipconazole 821–824 mode of action ipfencarbazone 358, 363, 368–371 classification 1000 ipfentrifluconazole 829 compound rules 1001, 1008 iprovalicarb 845, 850–853, 855, subgroups 1008–1009 862–865, 871, 876 objectives of 996 isofetamid 689 resistance management 1000–1001, isopyrazam 689 1008 isotianil 959, 969, 972–974 resistance principles disease control spectrum of 970 nontarget‐site resistance 1001 gene expression 975 target‐site resistance 1000 profiling experiments 969–975 structure and organization synthesis 968 of 996–997 systemic acquired sub‐groups 1008–1009 resistance 968–969 insecticide resistance management isoxaben 392, 395–398, 400, 402, 403, (IRM) 407, 411, 413, 414

bindex.indd 1672 12/21/2018 3:11:04 PM Index 1673

isoxadifen‐ethyl 82–84, 152, 157, 164, channel block, mechanism 1457 167, 245, 275, 436, 446 GABA receptors 1455–1456 isoxaflutole (IFT) 164, 165, 244, 254, glutamate‐gated chloride 292–296, 298, 437, 438, 564 channels 1456–1457 isoxazoles 295, 296, 299, 642 light‐harvesting‐complexes isoxazolines 373 (LHCs) 214 fenoxasulfone 380–383 Linepithema humile 1465–1466 pyroxasulfone 374–380 Liriomyza spp. 1535–1536 Ixodes scapularis 1467 Locusta migratoria 1024, 1249, 1506 Lolium spp. j L. multiflorum 16, 20, 22, 67, 82, jasmonic acid (JA) 579, 961, 964, 967 162, 464–465 juvenoids 1049–1050 L. rigidum 13, 16–18, 20, 22, 23, 25, chemical structures of 1050–1051 26, 49, 67, 359, 360, 376, 465, 4‐phenoxyphenyl 1051–1052 507 synthetic 1050–1051 Lotka‐Volterra predator‐prey target insects 1051–1052 model 1607 l‐phosphinothricin 481, 486 k lufenuron 1073, 1074 ® Ketospiradox 264 Lumax 273 Korrigan 392, 409 Lumbriconercis heteropoda 1229 ® kresoxim‐methyl 595, 600, 637, 642, Luna 701 644, 652, 653, 656, 659, 661, 1175 lycopene cyclase (LCC) 217–218, 454 Lygus spp. 1355, 1357, 1465, 1517 l Lymnaea stagnalis (Ls‐AChBP) 1233, labeled crops and use patterns 1537 1268, 1297 Lactuca serriola 18, 19, 49 Laodelphax striatellus 1285, 1286, m 1298, 1394, 1454, 1510 maize 82–84 Leotiomycetes 881 safener isoxadifen‐ethyl 82–84 lepidine 743, 744 sulfonylurea herbicides 82 lepidoptera pests 1030, 1298, 1495 maleic hydrazide (MH) 574 Lepidosaphes ulmi 1211 malonoben 708–710 lepimectin, synthesis of 1487 mandelamide 857–860 Leptocorisa spp. 1465 bioisosteres 860 L. decemlineata 1016, 1029, 1032, mandelic acid amides 845 1073, 1247, 1281, 1303, 1323, mandipropamid 856–860 1446, 1465, 1491 mandestrobin 644, 645, 672 Leucinodes orbonalis 1112 mandipropamid 845, 856–860, ® Lexar 273 863–865 ligand‐binding domains (LBDs) Manduca sexta 1055, 1068, EcR 1026 1106–1107, 1249, 1432, 1447, HvEcR 1021, 1022, 1026, 1028 1488, 1491 ligand‐gated chloride channel homolog MBI‐D fungicides (MBI‐Ds) 882, 885, 3 (LCCH3) 1455, 1456 889, 896, 904, 905 ligand‐gated chloride channel structure mectins 1592, 1593 binding site, structure 1457–1458 mefenacet 363–366, 371

bindex.indd 1673 12/21/2018 3:11:04 PM 1674 Index

mefenpyr‐diethyl 67, 69, 152, 157, 167, Peldon Al and Lincs El 23 297, 298, 427, 428, 434–435, 437, metabolic fate, sulfonylureas 87–88 441, 444–446 metabolism mefentrifluconazole 829 hydrolysis 1468, 1470 melanin biosynthesis inhibitor (MBI) photolysis 1468, 1469 fungicides soil degradation 1470 DHN biosynthetic transport and metabolism 1470 pathway 882–888 metabolite 1,2‐benzothiazole‐3(2H)‐ scytalone dehydratase one‐1, 1‐dioxide (BIT), 964 inhibitors 882, 885, 889 metabolite 4‐methyl‐1,2,3‐ melanin synthesis 603, 605, 879–906 thiadiazole‐5‐carboxylic Meligethes aeneus 1303, 1510 acid 968 membrane permeability transition metaflumizone 1446–1447 (MPT) 704 chemical structures of 1440 menadione 703 cross‐resistance mepanipyrim 728, 749, 750, 752, 754 potential 1447–1448 mepronil 685, 696, 1176 initial synthetic meptyldinocap 707, 715 methodology 1440–1441 mesoionic insecticides insecticidal activity 1446 biological profile 1393–1395 mode of action 1446–1447 chemical synthesis 1388–1389 N‐phenylpyrazoline isomer 1441 discovery of 1385–1386 pyrazoline isomers 1441 3H‐IMI 1390 metalaxyl 876, 917, 918, 934, 949, IMI 1389–1390 954–956 initial optimization of 1386–1388 metalaxyl 3 949, 950, 954 insect vs. vertebrate 1249 metalaxyl‐M 950 mammalian, environmental biological activity 954 safety 1395–1396 chemical and physical mechanism of 1393 properties 952 mode of action 1244, 1389–1393 chemistry of 949–953 nAChR 1392 degradation and metabolism, of P. americana 1390 enantiomers 956 mesosulfuron‐methyl 56, 63, 67, enantioselective catalysis 953 69–70, 435, 441, 445, 446 invention pathway of 950 metabolic pathway 87, 89 mode of action and mechanism of mesotrione 248, 275 resistance 954–956 in planta metabolism 273 synthesis of 951 in soils 273 metamitron 530, 549, 558, 560 technical synthesis 274 Metaseiulus occidentalis 1492 meta‐biphenyl carbazates 1186 meta‐substituted biphenyl metabolic detoxification carbazates 1186 cytochrome‐P450 monooxygenase metazosulfuron 56, 81 system 21 metconazole 574, 820–823 glutathione‐S‐transferase 21 methiopyrsulfuron 71, 72 GST 23 methoxyacrylate fungicides 1518 HPPD‐inhibitors 24 methoxyacrylate pharmacophore 670, L. rigidum 22, 23 1518

bindex.indd 1674 12/21/2018 3:11:04 PM Index 1675

methoxycarbamate 645, 654, 659 structure 1486 methoxy carbamate mite growth inhibitors pharmacophore 645 clofentezine 1086–1091 3‐(2‐methoxyethoxy)‐2‐methyl‐4‐ developmental stages 1086 (methylsulfonyl)benzoic diflovidazin 1086–1091 acid 299 etoxazole 1094–1101 methoxyfenozide 1017–1018, 1035, hexythiazox 1091–1094 1038–1039 structures of 1086 BAH 1034 miticide benzoximate 934 environmental fate 1039–1041 mitochondrial electron transport (MET) metabolism 1039–1041 complex I 4‐[(methylamino)]‐2‐(5H)‐ fenpyroximate 1163–1164 furanone 1362, 1363 pyridaben 1164–1165 methyl benzo[1,2,3]thiadiazole‐7‐ pyrimidifen 1168, 1169 carboxylate 965 tebufenpyrad 1166, 1167 methyl salicylate (MeSA) 961, 966, 974 tolfenpyrad 1166, 1168 2‐methyl‐6‐solanesyl‐1,4‐benzoquinone complex II cyenopyrafen 1168, (MSBQ) 243 1170, 1171 metolachlor 355, 359, 360, 375, 376, complex III 429–431, 443, 564, 949, 950 acequinocyl 1181–1182 metominostrobin 637, 642, 655, experiment 1189–1193 657–659 fluacrypyrim 1182 metrafenone 937 hydramethylnon 1183 cross resistance and mode of resistance mechanisms 1194 action 938 mitogen‐activated protein kinase kinase fungicidal profile 938 kinases (MAPKKKs) 761 manufacturing process 938 mitogen‐activated protein kinases 963 registration, products, formulations mixed function oxidases (MFOs) 102, and crops 939 1150, 1151, 1154, 1471 metribuzin 15, 163, 365, 469–473, modern agriculture, PGRs 530, 549, 560, 564 fruiting and growth 577 microtubulin assembly inhibitor (MAI) fruit storage and ripening 577 dithiopyr growth inhibitors 574–576 biology of 494 growth promotion 576 environmental fate 495 plant regulators in 575 synthesis 497–499 sprout inhibition 578 mode of action 496–497 stress defense 578–580 thiazopyr Molecular dynamics (MD) biology 494–495 calculations 36, 504, 891, 1377 environmental fate 495 mollusc AChBPs 1236 synthesis of 497–499 Monomorium pharaonis 1466 toxicology 495–496 monosulfuron 56, 71–72 milbemectin 1480 monosulfuron‐ester 56, 72 crop protection 1497 morpholines 829–831, 934 mites and insects 1491 MRL regulation 544 milbemycins multidrug resistance mechanism 764, chemistry of 1485–1488 773

bindex.indd 1675 12/21/2018 3:11:04 PM 1676 Index

multiple resistance 14, 25–26, 597, organophosphates 773, 918, 1146 (OPs) 1588–1591 Musca domestica 1053, 1237, 1247, soil fumigant 1587, 1588 1284, 1286, 1373, 1374, 1406, spirotetramat 1607–1608 1463 neonicotinoids 1242–1243, 1248, Mutation dependent 1268, 1501, 1510 Biomacromolecular Quantitative five‐membered ring systems Struture Activity Relationship imidacloprid 1293–1300 (MB‐QSAR) 47 thiacloprid 1300–1305 myxothiazols 616, 617, 638, 652 insect vs. vertebrate 1247 Myzus persicae 1099, 1212, 1213, mode of action insects 1242–1243 1216–1219, 1244–1246, noncyclic neonicotinoids 1248–1250, 1252, 1274, 1275, acetamiprid 1273–1276 1299, 1321, 1323, 1336, 1340, clothianidin 1276–1282 1341, 1350, 1361, 1365, 1369, dinotefuran 1282–1286 1372, 1373, 1389, 1390, 1453, nitenpyram 1270–1273 1506, 1519 vs. ring systems 1286–1288 structural segment 1265–1268 n thiamethoxam N‐acetyl‐phosphinothricin 486, 487 six‐membered 1309–1311 nAChR types of 1265–1266 butenolide 1244 nereistoxin 1223 mesoionic insecticides 1244 mode of action insects 1241–1244 nereistoxin and analogues 1242 neurotransmitter‐gated ion spinosyns 1243–1244 channels 1234 sulfoximines 1244 N‐formyl‐anilines 750 N‐amino heterocycles 1502 3‐[(N‐heterocyclyl) iminomethyl] N‐amino triazolinones 562 pyridines 1502 1,8‐naphthalic anhydride (NA) 427, N‐hydroxy‐anilinopyrimidines 751, 442–443 752 N‐aryl lactams 410–411 Nicotiana spp. nematicides N. plumbaginifolia 37 abamectin (AvictaTM) N. tabacum 37, 45, 46, 397 biological activity 1593–1594 nicotinamide adenine dinucleotide mode of action 1592–1593 (NADH) 460, 609–614, 623, biological 1586 703, 727–744, 756, 918, 1156, bionematicide 1631 ClarivaTM 1606–1607 nicotinic acetylcholine receptor VotivoTM 1605–1606 (nAChR) 1454 carbamates 1588–1591 AChBPs 1233–1234 in development competitive modulators fluazaindolizine 1603–1604 acetylcholine‐binding tioxazafen 1604–1605 proteins 1240–1241 fluensulfone (NimitzTM) pharmacophore models 1238–1240 1594–1602 evolution of 1224 fluopyram 1602–1603 gene family 1231 in markets 1587 insect 1236–1238

bindex.indd 1676 12/21/2018 3:11:04 PM Index 1677

insect vs. vertebrate 1244–1249 benzoheterocyclic to butenolides 1249 heterocycle 188–192 mesoionic insecticides 1249 N‐phenyl heterocycles 182–186 neonicotinoids 1247–1248 phenoxyphenyl and benzyloxyphenyl spinosyns 1248 to heterocycle 187–188 sulfoximines 1248 phenyl by benzyl ring ligand binding sites 1234–1236 replacement 192 mesoionic insecticide 1389–1393 phenyl with pyrazole ring mode of action insects replacement 192–193 butenolide 1244 pyridinecarboxamides 193 mesoionic insecticides 1244 noncompetitive antagonist neonicotinoids 1242–1243 (NCA) 1451–1453, 1455, 1457, nereistoxin and analogues 1242 1458, 1460 spinosyns 1243–1244 noncompetitive/open‐channel blocker nereistoxin and analogues 1242 (NCB) 1242 recombinant hybrid noncyclic neonicotinoids insect 1249–1251 acetamiprid 1273–1276 spinosyns MoA 1404–1406 clothianidin 1276–1282 structure of 1230–1233 dinotefuran 1282–1286 whole cell voltage clamp 1251–1256 nitenpyram 1270–1273 agonists vs. vs. ring systems 1286–1288 antagonists 1254–1256 nonsteroidal ecdysone agonist 1013, electrophysiology vs. radioligand 1016, 1022, 1026, 1044 binding studies 1252–1254 nontarget‐site resistance 14, 1001 nicotinoids 1229, 1234, 1245, 1247, enhanced metabolic 1253, 1256 detoxification 21–24 nikkomycin Z, chitin 1070, 1071 herbicide distribution 24–25 Nilaparvata lugens 1075, 1249, 1272, norflurazon 213, 217, 218, 223, 1298, 1323, 1386, 1394, 1464, 232–234, 237, 243 1510, 1555 norflurazone 234 nitenpyram 1270–1273 novaluron 1073 chemical classification 1270–1271 noviflumuron 1073 physicochemical properties of 1271 N‐phenylpyrazoles 193 use of 1272 N‐phenylsulfonylimidazopyridine‐2‐ nitisinone 241–243, 245, 248 carboxamide lead 2‐nitrobiphenyl 687 compound 1603, 1604, nitroimino‐heterocycle 1310–1312, 1643–1645, 1647 1316, 1318 N‐(4‐pyridyl/4quinolinyl) aryl 2‐nitroimino‐hexahydro‐1,3,5‐ acetamides 735 triazines 1315 N‐sulfonyl amino acid amides 856 4‐nitroimino‐1,3,5‐oxadiazinane 1311, N‐triazolo[1,5‐a]pyrimidine 1315, 1318 sulfonamides N,N‐dimethylamino‐1,2‐dithiolane‐4‐ biology 114–115, 118–119 amines 1229 pyroxsulam N‐(N’,N’‐dimethylaminosulfonyl) crop selectivity 115–117, azoles 664, 666–667 119–121 nonclassical Protox chemistries crop utility 115, 119

bindex.indd 1677 12/21/2018 3:11:04 PM 1678 Index

N‐triazolo[1,5‐a]pyrimidine organophosphates (OPs) 1073, 1146, sulfonamides (contd.) 1210, 1229, 1336, 1436, 1440, ecotoxicology, and 1501, 1549, 1574, 1586, toxicology 117–118, 121–122 1588–1591, 1615, 1636 environmental organophosphorous (OPs) 1530 degradation 117–118, 121–122 orthosulfamuron 56, 57, 80–81 synthesis 118 orysastrobin 644, 655, 658, 669 N‐triazolo[1,5‐c]pyrimidine Oryza sativa 73, 115, 117, 140, 148 sulfonanilide ossamycin 625 biology 109 Ostrinia nubilalis 1031, 1108–1109, cloransulam‐methyl and diclosulam 1119, 1121, 1464, 1573 crop selectivity 110 Otiorhynchus sulcatus 1467 crop utility 110 oudemansin 641 ecotoxicology, and oudemansin A 587, 634, 638 toxicology 111–112 oxadiargyl 178 environmental oxadiazine degradation 111–112 insecticides 1427 florasulam synthesis of 1428 crop selectivity 110–111 1,3,4 oxadiazolon‐3‐yl ketones 1502 crop utility 110 oxasulfuron 57, 58, 84–85 ecotoxicology, and toxicology 112 oxathiapiprolin environmental degradation 112 biological activity, potency and synthesis 108 effect, on fungal life synthetic routes 108 cycle 982–984 nucleic acid synthesis 599, 949–956, discovery and 1538 optimization 980–982 Nymphalis spp. 1465 environmental toxicology 986 mammalian toxicology 985 o physical properties 985 ® Oberon site of action studies 984–985 ACCase 1212 oxidative phosphorylation 1150 IPM 1218–1219 aerobic organisms 610 ochratoxin A (OTA) 773 ATP synthesis 610 Odontotermes takensis 1464 chemistry 1151–1153 Oebalus spp. 1465 chlorfenapyr resistance 1154 oligomycin 625, 1138 diafenthiuron 3‐O‐methyldopamine 857, 858 biological activity 1144–1146 Oncopeltus fasciatus 1050, 1069, structure–activity relationship 1071 (SAR) 1141–1144 oomycete pathogens toxicology and carbendazim and BZ 788 ecotoxicology 1144 EC50 values 789 dioxapyrrolomycin 1149–1150 mutation C239S 787 energy conservation and nonoomycete fungi 785 F1F0ATP synthase 624–627 resistance risk 791–792 mitochondrial ADP/ATP O‐pyrimidinylsalicylic acids 129 carrier 627–628 organochlorine‐resistant (OCR) 1454 inhibitors and uncouplers 611

bindex.indd 1678 12/21/2018 3:11:04 PM Index 1679

mitochondrial ATP and acute oral toxicity 219 synthase 1137–1139 enzyme activity 219 mitochondrial electron transport phenoxybenzamides 219 chains phenoxypyridincarbonamides 219– alternative electron transport 223 chains 623–624 phenoxypyridine ethers 223 complex I and inhibitors 612–614 phenylfuranones 223 cytochrome bc1 complex and phenylpyridazinones 223–225 inhibitors 614, 616–617 phenylpyridinones 225–226 cytochrome c oxidase and phenylpyrrolidinones 226 inhibitors 617, 620 phenyltetrahydropyrimidinones succinate 226–227 dehydrogenase 620–623 physical data 219 mode of action 1139–1141, structural overlay 227–231 1150–1151 structural requirements 231–232 pest species and pectin methylesterase (PME) 412 markets 1153–1154 Pefurazoate 810–812 uncoupler/phosphorylation Penconazole 813 inhibitor 611 pencycuron 590, 599, 1299 UQ binding sites 611 penoxsulam oxime ethers 400, 401, 431–432, 641, crop selectivity 115–117 642, 645, 654, 660, 861, 1053 crop utility 115 oximino amides 642–644, 654, 658, environmental degradation, 659 ecotoxicology, and oximino ester toxicology 117–118 pharmacophore 642 pentachlorobenzyl alcohol strobilurins 642 (PCBA) 882 trifloxystrobin 643 pentanochlor 531 oximino pharmacophores 668 penthiopyrad 685, 688, 689, 699, 1176 oxpoconazole 811–812 pentoxazone 75, 181 oxyacetamide 355, 358–360, 363–371 Periplaneta americana 1068, 1070, oxycarboxin 681, 682 1244, 1247, 1252, 1284, 1348, oxysterol binding protein (OSBP) 588, 1389, 1390, 1433, 1435, 1457, 979, 984, 986 1544, 1568 ® Permit 431 p persistent, bioaccumulative, and toxic paclobutrazol 574, 577, 578, 800 substance (PBT) 547, 548 ® Paicer 290 persistent organic pollutant (POP) 546 PaladinTM 1588 Phacelia tanacetifolia 1346, 1381 Panonychus spp. 1089, 1093, 1171, pharmacophore 639, 641, 643, 645, 1177, 1187 647, 655, 669, 1238, 1240, 1241, P. citri 1188, 1488 1309, 1362, 1365 P. ulmi 1090, 1188, 1203, 1205 models 1238–1240 paraquat 24 types 1267 Parnellophore 1461 phenmedipham 530, 549, 558 Pasteuria spp. 1606–1607 phenoxan 743 PDS inhibitors phenoxybenzamides 219

bindex.indd 1679 12/21/2018 3:11:04 PM 1680 Index

phenoxyphenoxypyrimidine 126, 187 PPP Regulation 545–548 phenoxyphenyl and benzyloxyphenyl to EU re‐registration heterocycle 187–188 buffer zone restriction 543 phenoxypyridincarbonamides dietary intakes, of pesticides 219–223 residues 540 phenoxypyridine ethers 223, 224 EPPO risk‐assessment phenylacetic acid amides 738–740 schemes 542–543 phenylamides 589, 596, 599, 865, 871, fate and behavior of pesticide, in 955, 956 environment 540–541 fungicides 954 Good laboratory practice resistance 955 (GLP) 538 phenylcarbamates desmedipham 549 honeybee risk assessment 543 phenylfuranones 223 nontarget terrestrial arthropods, phenylpyrazoles 21, 194, 195, 197, effects on 544 1449, 1452, 1510 operator exposure data phenylpyridazinones 223–225 requirements 539 phenylpyridinones 225–226 physical and chemical 1‐phenyl‐1‐pyrimidinyl‐ characteristics of hydrazines 752 preparations 539 phenylpyrimidones 200 physical and chemical properties, phenylpyrrole 600, 761–764, of active substances 538–539 767–776 residue data chemistry 768–771 requirements 539–540 foliar and post‐harvest storage stability 539 usage 771–774 Hill reaction 530 mode of action 761 HRAC classification 532 Protox inhibitors 196 PS II inhibitors seed treatment 774–776 amicarbazone 559–564 phenylpyrrolidinones 226, 231 in EU Markets 548–557 2‐phenyl‐4,5,6,7‐ market share 558 tetrahydro‐2H‐indazoles 197 photosystem (PS) II inhibitors 15, 365, phenyl tetrahydrophthalimides 177, 394, 529 179–182, 188 phthoxazolin A 415 phenyltetrahydropyrimidinones p‐hydroxyphenylpyruvate (HPP) 24, 226–227 241, 242, 245–249 phenyluracils 200 phytoene desaturase (PDS) 215, 242 Phorodon humuli 1216 inhibitors 234–237 phosphinothricin 452, 476, 477, and ζ‐carotene desaturase 217 479–488 phytophagous mites 1085, 1142, 1171, phospholipid biosynthesis 846, 864 1172, 1174, 1187, 1482 photoaffinity labeling 614, 621, 1256, Phytophthora infestans 603, 665, 707, 1545 734, 791, 849, 871, 874, 914, 950, photosynthesis inhibitors 979 approval process, for active Phytoseiulus persimilis 1101, 1518 substances, in EU 532–538 picloram 308–311, 315, 318, 321, 324, EU regulation 336, 346 MRL regulation 544 picolinafen 222, 233, 234, 238

bindex.indd 1680 12/21/2018 3:11:04 PM Index 1681

picolinic acid 97, 266 polyoxin D, chitin 1070, 1071 picoxystrobin 643, 656, 657, 659 ponasterone piericidin 614, 1156 hydrogen bond interactions 1026 Pieris rapae 1465 relative positions 1027 PinpointTM 943 Popillia japonica 1038, 1467 piperazines 203, 415, 614, 806–812, powdery mildew fungicide 980 cyflufenamid piperidines 829–831 cross resistance and mode of piperidinyl thiazole 979, 980, 986 action 934–935 piperonyl butoxide (PBO) 1043, 1050, discovery 933–934 1140, 1151, 1471 fungicidal profile 936 Planococcus citri 1094, 1099, 1100, manufacturing process 935–936 1178, 1219, 1275 flutianil 943–945 plant growth regulators (PGRs) 800 metrafenone auxins 573 cross resistance 938 chemical structures of 573, 576 formulations and crops 939 cytokinins 574 fungicidal profile 938 ethylene 573 manufacturing process 938 gibberellins 573–574 mode of action 938 modern agriculture registration, products 939 fruiting and growth 577 proquinazid fruit storage and ripening 577 discovery 941–942 growth inhibitors 574–576 fungicidal profile 943 growth promotion 576 manufacturing process 942 sprout inhibition 578 registration, products, stress defense 578–580 formulations and natural categories 573 crops 942–943 plant nitrogen metabolism 477–479 pyriofenone plant‐parasitic nematodes 993, 1586, cross resistance and mode of 1587, 1593, 1594, 1603–1606, action 940 1615, 1636–1637, 1643–1652 manufacturing process 940 plant protection products registration, products, formulations (PPPs) 532, 536, 537, 539, and crops 940–941 543–545, 558, 591 prephytoene pyrophosphate plant regulators (PRs) 326, 571–580 (PPPP) 215, 216 plastoquinone (PQ) 24, 213, 214, 232, probenazole 604, 905, 959, 963, 964 242 profluazol 181, 182 Plodia interpunctella 1114 propanil 531 Plutella xylostella 1030, 1056, 1108, propiconazole 812 1114, 1116–1117, 1275, 1362, propoxycarbazone‐sodium 151, 163 1385, 1405, 1437, 1447, 1465, physico‐chemical properties 153 1531, 1546, 1558, 1563 propyrisulfuron 56, 81 polychlorocycloalkane (PCCA) 1451 proquinazid polygalacturonase 412 discovery 941–942 polyketide synthase (PKS) 588, 882, manufacturing process 942 883, 1407 prothioconazole 701, 821, 827–829, poly‐N‐acetyl‐glucosamine 1067 925, 1281

bindex.indd 1681 12/21/2018 3:11:04 PM 1682 Index

prothoracicotropic hormone Pseudaulacaspis (PTTH) 1055, 1056 pentagona 1060–1061 proton‐gated chloride channels 1457 Psylla pyri 1211 protonophoric uncouplers 704–706, pydiflumetofen 689 708–710, 717 pyflubumide protoporphyrin IX (PPIX) 20, 174, chemical structure 1173 204 cross‐resistance 1177–1178 protoporphyrinogen IX (PPGIX) 20, in vitro selectivity 1179–1180 174, 187, 188, 194–195, 203, IRAC classification 1180–1181 1202 lead compound 1174–1175 protoporphyrinogen‐IX‐oxidase‐ mode of action 1178–1179 inhibitors (PPO) NH‐form of 1179–1180 inhibitors 1202 structure–activity relationship protoporphyrinogen oxidase 20 (SAR) 1176–1177 development synthesis 1177 aromatic meta position 199 synthetic pathway of 1202 diphenyl ether 174–176 toxicity 1178 2,4,5‐imidazolidinetriones 197 pymetrozine 1501 phenyl pyrrole 195 biological activity and use phenyl ring to recommendation of 1510 heterocycle 177–179 chemical and physical properties 2‐phenyl‐4,5,6,7‐tetrahydro‐2H‐ of 1506, 1509 indazoles 197 discovery 1502–1503 phenyl tetrahydrophthalimides insecticidal spectrum of 1510 179–182 mode of action 1506–1509 protoporphyrinogen IX 194–195 resistance 1509–1510 tetrahydrophthalimides 195 safety profile 1511 tetrasubstituted phenyl synthesis of 1506, 1508 pyrazoles 197 pyraclonil 81, 192, 193 nonclassical Protox chemistries pyraclostrobin 579, 643–645, benzoheterocyclic to 655–656, 659, 661, 671 heterocycle 188–192 pyraflufen‐ethyl 179 and benzyloxyphenyl to pyrametostrobin 645 heterocycle 187–188 pyraoxystrobin 635, 645 N‐phenyl heterocycles 182–186 pyrazole acetamide 980 phenoxyphenyl 187–188 pyrazoline isomers phenyl by benzyl ring facile oxidation 1442 replacement 192–193 new derivatives 1443 phenyl with pyrazole ring synthesis of 1442 replacement 192 pyrazolines 1424–1428, 1441, 1446 pyridinecarboxamides 193 pyrazolynate (pyrazolate) 288–291, resistant weeds control 203–204 293, 297 toxicology 204 pyrazoxyfen 241, 244, 290–293 Protox inhibitors pyrethroid insecticides, dust bicyclic heterocyclic ring 200 mites 1527 chemical structures of 175 pyrethroids 991, 1431, 1436, 1501, Pseudatomoscelis seriatus 1465 1530, 1535, 1554, 1558, 1574

bindex.indd 1682 12/21/2018 3:11:04 PM Index 1683

pyribencarb 639, 644–645, 672, 839 resistance 1521–1522 pyridaben 614, 663, 727, 1164–1165, synthesis of 1520–1521 1168, 1194, 1209, 1211 pyrimethanil 728, 749, 750, 753, 754, pyridalyl 756 beneficial arthropods 1536 pyrimidifen 1168, 1175, 1189 biological aspects pyrimidines 129, 227, 231, 261, 477, insecticidal activity and 734, 738, 749, 750, 806–812 uses 1535–1536 pyrimidinyl carboxy (PC) 140–141 mode of action 1536–1538 bispyribac‐sodium 136–137 chemistry discovery of 126–128 lead compound, mode of action 140–141 optimization 1532–1534 mode of selectivity 141–142 lead generation 1532 pyriminobac‐methyl 137–140 commercialising status 1539 pyrithiobac‐sodium 134–135 insecticidal activity structure–activity relationship (SAR) insecticide resistant strain 1535 O‐pyrimidinylsalicylic acids 129 lepidopterous pests 1535 pyrimidinylglycolates 129–133 physicochemical properties 1534 pyrimidinylglycolates 126, 128–133 structure 1531 pyrimidinyl hydrazones 716 toxological profile 1531 pyrimidinylsalicylates 126, 129, 143 pyridazine pyriminobac‐methyl 137–140, 142 insecticides 1426 pyriminostrobin 664, 1192–1193 synthesis of 1428 pyrimisulfan, sulfonanilides 147 pyridine azomethines 1502, 1504, pyrimorph 845, 849, 864 1506–1507, 1519 pyriofenone pyridinecarboxamides 193, 194 formulations and crops 940–941 pyridinyl‐ethyl benzamide manufacturing process 940 fluopyram 1630 products 940–941 agrophoric element 695–696 registration 940–941 biological activity and application pyriproxyfen rates 698–699 biological activity chemical structure of 694 field evaluations 1057–1061 cross‐resistance pattern 699–701 laboratory fluopyram synthesis 698 evaluations 1056–1057 ortho‐substituted benzamide resistance 1061–1062 residue 696 formulation 1063 physico‐chemical properties 695 juvenoid research 1050–1052 structural elements, on biological mechanism of action 1053–1056 spectrum 696–697 optical isomers 1053 pyrifluquinazon physico‐chemical properties 1062 biological activity and safety research process 1052–1053 profile 1522 stability 1063 bsafety profile of 1522 synthesis 1062 chemical and physical properties toxicology 1063 of 1521 pyrisoxazole 829 discovery of 1518–1519 pyrithiobac‐sodium 134–135 mode of action 1521 pyroquilon 882, 885

bindex.indd 1683 12/21/2018 3:11:04 PM 1684 Index

pyroxasulfone RinskorTM 344, 347 biological activities 375–376 RNA interference (RNAi) 148, 234, chemistry 374–375 1077, 1105, 1576 mode of action 376–380 root‐knot nematode (RKN) 1075, physicochemical properties 376 1488, 1593, 1600, 1603, 1605, pyroxsulam 1615, 1630, 1636, 1644–1645 crop selectivity 119–121 rotenone 609, 611, 614, 1156, 1157, crop utility 119 1163 ® ecotoxicology, and Roundup 455 toxicology 121–122 roundup hybridization environmental system 456–458 ® degradation 121–122 Roundup Ready Plus (RRP) soil metabolites of 122 program 467 ® pyrrolnitrin 767–769 Roundup Ready traits 455, 457 Roundup XtendTM 468, 470 q ryanodine receptor (RyRs) quantitative structure–activity alkaloid ryanodine 1541 relationship (QSAR) 187, 530, binding site and target‐site 821, 1071, 1096, 1240, 1341, 1409 resistance 1547 quasi‐cyclic neonicotinoids 1286 cryo‐EM structures 1542 quinolin‐6‐yloxyacetamides 785 diamides 1541 quinone outside inhibitor (QoI) 588, ER/SR stores 1541 592, 664, 701, 757, 774, 865, 927, excitation‐contraction (e‐c) 934 coupling 1542 quinoxaline 894 homotetrameric complexes 1542 quinoxyfen 744 voltage‐gated ion biology 778–779 channels 1542–1543 ® chemistry 776–777 Rynaxypyr 327–328, 1562, mode of action 765–766 1564–1565, 1571–1577 synthesis 778 s r Saccharomyces cerevisiae 37, 47, 354, regulatory subunits (RSU) 36–37, 141 614, 761 ® RESICORE 274 Saccharopolyspora spinosa 1229, 1400 residue definition 545, 547 safeners resistance management (IRM) agricultural practice insect control 1115 cyprosulfamide 446–447 P. xylostella 1116 dichloroacetamide 443–444 resistance management regulatory 998 fenclorim 444 resistance‐monitoring methods 596, fenoxaprop‐ethyl 444 998 flurazole 443 resistance mutation 507, 756, 789, fluxofenim 443 1453–1454 isoxadifen‐ethyl 446 respiration inhibitors 611, 628, 634, mefenpyr‐diethyl 444–446 648, 662, 694, 1189 1,8‐Naphthalic Anhydride Reticulitermes flavipes 1466 (NA) 442–443 Rhagoletis mendax 1466 cloquintocet‐mexyl 432–444

bindex.indd 1684 12/21/2018 3:11:05 PM Index 1685

cyprosulfamide 437 sodium channel blocker insecticide dichloroacetamide safeners (SCBI) 1437, 1446 benoxacor 429–430 sodium channel blockers 1424 dichlormid 431 discovery 1424 furilazole 431 pyrazoline 1424–1425 gene induction and signaling Sogatella furcifera 1286, 1394, 1454 pathways 440–441 soil degradation 87, 111, 185, 275, herbicide metabolism, effects 337, 432, 1041, 1396, 1470, 1564, of 438–440 1565 herbicide translocation 441–442 pathways, sulfonylurea 87 herbicide uptake 441 soil fumigant 1587, 1588, 1615 isoxadifen‐ethyl 436 Solenopsis invicta 1466 mechanism 428, 437–442 Sorghum halepense 18, 82, 109, 135, mefenpyr‐diethyl 434–435 400 oxime ethers 431–432 spinetoram 1402, 1413 SalibroTM 1603–1604, 1646, discovery of 1414 1649–1652 semi‐synthesis 1414 salicylic acid (SA) 129, 440, 459, 579, spinosad 580, 961, 964, 1300 biological activity 1402–1404 Salmonella typhimurium 33, 40, 141 structures of 1401 ® Sanbird 254, 288, 290 spinosyns 1404–1406 sangivamycin 416–417 biosynthesis 1416–1418 sarco‐/endoplasmic calcium ATPase insect vs. vertebrate 1248 (SERCA) catalyzes 1542 mode of action 1243, 1404–1406 Scapteriscus spp. 1467 natural products 1403 scytalone 588, 889, 893 resistance scytalone dehydratase (SD) 588, and cross‐resistance 1406 882–896 semi‐synthetic SDHI carboxamides 1174–1176, 1178, modifications 1406–1413 1181 spinetoram 1413–1416 ® Selectfluor 927 spirodiclofen selective homopteran feeding cyclic ketoenols 1202–1205 blockers 993, 1501 discovery of 1203 sethoxydim 16, 17, 454, 504, 508, 509, lipid decrease in 1209 934 synthesis of 1206–1207 Sida spinosa 135, 376, 1418 spiroketalamines 831–833 silthiofam 590, 628 spiromesifen simeconazole 826–827 cyclic ketoenols 1202–1205 single nucleotide polymorphisms discovery of 1203 (SNPs) 234, 905, 955, 984, 1625 efficacy of 1210 Sitophilus granarius 1415, 1463 synthesis of 1206–1207 ® Sivanto prime 1365 spirotetramat 1216–1218, 1607 crop‐insect pest spectrum 1374 discovery of 1212–1214 foliar vs. drench 1380 mode of action 1216 neonicotinoid insecticides 1375 physico‐chemical properties 1216 small brown planthopper synthesis of 1214–1215 (SBPH) 1286, 1454 transformation of 1217

bindex.indd 1685 12/21/2018 3:11:05 PM 1686 Index

Spodoptera spp. 1488, 1491 fungal resistance 664 S. eridania 1446, 1490 insecticidal and acaricidal S. exigua 1029, 1074, 1099, 1108, activity 662–664 1413, 1448 in vitro testing 634 S. frugiperda 1218, 1387, 1413, lead structures 1416, 1481 commercial potential 641–644 S. littoralis 1492, 1494 discovery of 637–641 S. litura 1054, 1532 metabolic degradation S. spp. 1531 rates 659–660 squalene epoxidase inhibitors 802, N‐(N’, N’‐dimethylaminosulfonyl) 803, 839 azoles 666–667 Standing Committee on Food Chain and patents and developmental/ Animal Health (SCFCAH) 537 commercial products 636 stemofoline 1361–1363 plant physiology and crop Stemona alkaloids 1361, 1362 yield 661–661 Stemonaceae 1361 research activities 645–648 Stenchaetothrips spp. 1464 synthesis routes 667 sterol biosynthesis inhibitors target activity 648–655 (SBIs) 589, 591, 753 transportation and in agriculture distribution 655–659 biochemical targets 799–802 strobilurins 798, 871 classes of 802–803 structure‐activity relationships market importance 799 (SARs) 327, 689, 980, 1488, 1550 amines acaricidal carboxamides 1176 biochemical targets 831 acaricide pyflubumide 1176 morpholines and analysis 374 piperidines 829–831 of anilinopyrimidines 753–754 spiroketalamines 831–833 bisacylhydrazines 1022–1023 amino‐pyrazolinones 835–836 of 7‐chloro‐4‐phenoxyquinoline 777 DMI fungicides diafenthiuron 1141–1144 piperazines, pyrimidines, and ecdysteroids 1019–1022 imidazoles 806–809 flubendiamide 1553 triazoles 812–829 flupyradifurone 1368–1369 hydroxyanilides 833–835 isomeric hydrazone 1445 squalene epoxidase inhibitors 839 O‐pyrimidinylsalicylic acids 129 Streptomyces spp. 1070, 1485 phenylpyrrole fungicides 770 S. avermitilis 1480, 1482 pyrimidinylglycolates 129–133 S. fumanus 1149 pyrimidinylsalicylates 129 S. hygrocopicus 1480 of strobilurins 648–661 S. hygroscopicus 1485 studies 364 strobilurin A 587, 634, 637–639, 648 substituent X Y Z 1444 strobilurin fungicides sulfonanilides ametoctradin 667 benzene ring substitution in 145–147 azolones 665–666 bridge moiety 144–145 biokinetic behavior 649 sulfonamide moiety 144 Chinese institutes and sulfoxaflor 1339–1341 companies 644–645 thiamethoxam 1311–1315

bindex.indd 1686 12/21/2018 3:11:05 PM Index 1687

triazolopyrimidine 107 discovery of 152 strychnine‐sensitive glycine optimization of 152–155 receptors 1455 synthesis suboesophageal ganglia 1506 sulfonyl component 158–160 succinate dehydrogenase (SDH) 588, triazolinone synthesis 161–162 592, 620–624, 681–691, TCM 155–157 694–701, 773, 1630 sulfonylureas (SUs) 39–40 biological activity and acute toxicity of 56–57 application 688–689 agricultural utility carboxylic amides cereals 61–72 active ingredients 685 crops 84–87 structure of 681 maize 82–84 metabolism 690 rice 73–82 pyridinyl‐ethyl benzamide development of 58 fluopyram 695 first generation 55, 56 research activities and patent introduced before 58–59 situation 686 metabolic fate and behavior, resistance 690 soil 87–88 structure–activity relationships synthesis 58–61 (SARs) 689 weed resistance 49 synthesis 686–688 sulfosulfuron 56, 65–66 sugar beet cyst nematode 1585, 1606 sulfoxaflor 1347–1349 sulcotrione 241, 243, 244, 258, 269, compatibility of 1353 270, 273–277, 293, 296 discovery 1337 soil metabolism 273 environmental toxicology technical synthesis 270 aquatic nontarget species 1347 sulfentrazone 173, 178, 199, 201, 203 terrestrial nontarget sulfonamides, species 1343–1347 triazolopyrimidine 106–107 French tunnel study 1346 sulfonanilides 148 global field uses 1352–1358 discovery of 142–143 global uses 1355 mode of action 148 mammalian toxicology 1342 pyrimisulfan 147–148 mode of action 1347 structure–activity relationship (SAR) physico‐chemical, environmental fate benzene ring substitution in 145 properties 1342 bridge moiety 144–145 resistance and cross‐resistance 1349 sulfonamide moiety 144–147 spectrum of activity 1351–1352 sulfonylaminocarbonyl‐triazolinones structure–activity relationship (SACTs) (SAR) 1339–1341 biology synthesis of 1337–1339 cereals grass control 166 trade names 1352 flucarbazone‐sodium 162–166 sulfoximine 1337 propoxycarbazone‐sodium 163 HPPD inhibitors 262 TCM 163 insect vs. vertebrate 1248 thiencarbazone‐methyl 165 mode of action 1244 inhibitors of 152 progression of 1336 lead structure synthetic routes 1338

bindex.indd 1687 12/21/2018 3:11:05 PM 1688 Index

systemic acquired resistance 6‐tetrahydro‐fur‐3‐ylmethyl (SAR) 579, 603, 685, 717, 959, (TFM) 1282 961–964, 966–968 tetrahydrophthalimide Protox inhibitors 177, 195 t tetrahydrophthalimides 174, 179, 180, TalinorTM 278, 433 182, 183 ® Talius 943 tetrahydroquinolines 1044 target‐site resistance 14, 1000 1,3,6,8‐tetrahydroxynaphthalene acetolactate synthase (ALS/AHAS) reductase 880, 882, 885, 898 inhibitors 18–19 2,2,4,4‐tetramethyl‐cyclohexane‐1,3,5‐ acetyl‐CoA carboxylase (ACCase) trione moiety 259 inhibitors 15–18 1,1,3,3‐tetramethylguanidine 5‐enolpyruvylshikimate‐3‐phosphate (TMG) 328 synthase (EPSPS) 20 tetramic acid 519, 520, 1005, 1202, photosystem II (PS II) 1212, 1214, 1608 inhibitors 15 Tetranychus spp. 121, 1089–1091, protoporphyrinogen oxidase 1093, 1171, 1177, 1187, 1209 (PPO) 20–21 T. cinnabarinus 1145, 1491, 1496 tebuconazole 574, 604, 813, 821, 827, T. urticae 510, 1090, 1092, 1094, 828, 925, 1299 1096, 1099–1101, 1121, 1145, tebufenozide 1016, 1017, 1022–1025, 1149, 1154, 1171–1173, 1178, 1029–1034, 1042, 1043, 1045 1180, 1184, 1185, 1187, 1194, tebufenpyrad 663, 727, 1158, 1163, 1202–1205, 1207–1209, 1212, 1166–1168, 1194, 1195 1218, 1219, 1488–1494, 1496, tebufloquin 1497, 1555 chemical structure 925–926 development stages 1187 physicochemical properties 926 tetrazines 1086–1091, 1093 protective and curative tetrodotoxin‐resistant (TTX‐R) 1435 conditions 927 tetrodotoxin‐sensitive (TTX‐S) 1435 rice disease and rice blast 925 thaxtomins 413–415 synthesis of 926 thiacloprid 1300 toxicological and environmental activity of 1304 studies 927 chemical classification 1301 teflubenzuron 1072, 1073 ovicidal activity of 1304 tefuryltrione 258, 265, 272, 273, physicochemical properties 1301 275–277 synthetic pathways 1302 tembotrione 24, 164, 165, 244, 245, thiadiazoles 8, 9, 21, 360, 364, 254, 258, 265, 272–276, 436, 437 603, 965 commercial formulations 277 thiamethoxam 1320–1322 soil degradation 275 AKD‐1022 1316–1317 synthesis of 276 CGA 293’343 1317–1331 tentoxin 625, 626 chemical and physical properties terbinafine 838, 839 of 1319–1320 terrestrial nontarget discovery 1318 species 1343–1347 ecological toxicology 1328 tetrachloropicolinic acid 321, 322 hydrolytic degradation tetraconazole 813–814, 943 pathways 1320

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insecticidal relevance corn and soy yield 1622 metabolism 1322 corn plants 1617 mode of action 1320–1322 cotton lint yield 1621, 1622 nitroimino‐heterocycles 1316 crops 1627 physico‐chemical properties 1319 and environmental fate 1623 resistance 1323–1325 formulation 1624–1625 safety profile 1325–1327 growing regions 1617 six‐membered neonicotinoids large scale production 1625–1627 1309 mode of action 1625 structure–activity relationship physical properties 1623 (SAR) 1311 row crops damage 1616 synthesis 1315, 1318–1319 SCN sampling 1617 vigor effect 1327–1331 seed treatment yield 1617 thiamine diphosphate (ThDP) 33 TIR1/AFB auxin receptors 306–309 thiatriazines 407–410 tolfenpyrad 601, 1159, 1163, thiazolidinone acaricides 1091, 1093 1166–1168, 1195 thiazolidinone carbamate 397, 410, tolprocarb 411 biological activity 902–904 thiazopyr inhibiting PKS activity 898 biology 494–495 tolpyralate 298–301 environmental fate 495 tomato spotted wilt virus synthesis of 497–499 (TSWV) 970, 1299, 1465 thiencarbazone 275, 297, 436, 437 topramezone 244, 264, 295–299, 301 physico‐chemical properties 153 Torpedo marmorata 1233–1235 thiencarbazone‐methyl (TCM) 152, 3D structure 1238 153, 155–158, 163, 165, 166, 293, Torpedo nAChR 1233, 1235, 1254, 446 1256 discovery of 155 toxicokinetics and metabolic fate sulfonylaminocarbonyl‐triazolinones in animals 1471 (SACTs) 151 in insects 1471 thifluzamide 682, 685–688, 1175 transient receptor potential channels thioacetamide 686 (TRPV) 1502, 1509, 1517, thiocarbamate pyributicarb 803 1521 thiolcarbamate 1052, 1053 transmembrane‐spanning 5‐thiono‐1,2,4‐oxazolidinone 1143, domains 1231 1144 transmission electron microscopy Thrips spp. 1464 (TEM) 902, 903, 1538 T. palmi 1058, 1275, 1285, 1405, trehalose 1068 1465, 1535–1536 triadimenol 807, 812, 925 T. tabaci 1465, 1517 Trialeurodes vaporariorum 1056–1058, tiadinil 604, 605, 685, 959, 960, 964, 1145, 1219, 1285, 1298, 1323, 967–968, 971 1356, 1374, 1376, 1510, 1522 tiafenacil 202 triazines 4, 15, 22, 82, 297, 529, 549 tioxazafen 1604 herbicides 15, 274, 403, 558 Collinsville, IL. 1617, 1620 1,3,5‐triazines 531 commercial standards 1616, triazinones 8, 201, 529, 549, 553, 1619–1622 561

bindex.indd 1689 12/21/2018 3:11:05 PM 1690 Index

triazole fungicides 596, 799 discovery of 1386–1388 bromuconazole 819 insecticidal activity 1394 epoxiconazole 816 nontarget organisms 1396 fenbuconazole 814 physicochemical properties fluquinconazole 824 of 1388 imibenconazole 825 toxicity of 1397 ipconazole 822 trifluoroacetic acid (TFA) 328 mefentrifluconazole and trifluoromethylnicotinamides 1511, 1513 ipfentrifluconazole 829 insecticides 1512 metconazole 820 structure–activity relationships 1515 prothioconazole 827 triketones pyrisoxazole 829 commercialised triketone herbicides simeconazole 826 benzobicyclon 278 tetraconazole 813 mesotrione 274 triticonazole 818 sulcotrione 273 triazolinone 8, 152, 161–162, 178, 179, tembotrione 276 182–184, 201, 363, 368–371, 562, discovery 253 647 mode of action 253–255 triazolo[1,5‐a]pyrimidine patent literature sulfonanilides 107, 123 BASF triketones 263 triazolocarboxamides 9, 12, 401–403 Bayer CropScience commercialized triazolopyrimidine triketones 265 acetohydroxyacid synthase (AHAS) Bayer CropScience inhibition 122–123 triazolylpyridine flumetsulam 107 triketones 266 N‐triazolo[1,5‐a]pyrimidine Dow triketones 265 sulfonamides 118–122 6,6 heterocyclic type II bicyclic N‐triazolo[1,5‐c]pyrimidine aroyl systems 267 sulfonamides 108, 112–118 Idemitsu and DuPont sulfonamides 107 triketones 264 triazoxide Ishihara Rice triketones 265 chemical structure 923 Nippon soda types 261 physicochemical properties 924 Nissan triketones 262 seed treatment 925 ‘One’ HPPD inhibitors 268, 269 synthesis of 923 pyridines and pyrimidines 262 tricarboxylic acid cycle (TCA) 1631 Syngenta pyridyl triketones 266 trichloroisocyanuric acid (TCIA) 791 Syngenta triazolopyridine tricyclazole 605, 882, 885, 899, 1299 triketones 267 trifloxystrobin 601, 636, 637, 642, 643, Zeneca patents 260 654–657, 659, 663, 668 structure–activity trifloxysulfuron‐sodium 58, 86–87 relationships 257–259 trifludimoxazin 202 synthesis of 255–257 triflumezopyrim 1385 triticonazole 818–819 biological profile of 1393–1395 Triticum aestivum 62, 111, 119, 120, chemical synthesis 1388–1389 151 comparative activity 1395 tritosulfuron 56, 57, 69–71

bindex.indd 1690 12/21/2018 3:11:05 PM Index 1691

Tuta absoluta 997, 1036, 1406, 1437, v 1447, 1574 validamycin 590, 606, 1273, 1280 two‐spotted spider mite (TSSM) 1086, valifenalate 845, 853–855 1096, 1099, 1101, 1149, 1184, 1189, valinomycin 704 ® 1194, 1202, 1218, 1488–1491, VaporGrip 468–470 1493, 1494, 1496, 1497 vegetative insecticidal proteins Type I polyketide synthase 1417 (Vips) 1104 Tyrophagus putrescentiae 1528 Velum TotalTM 1603 tyrosine 24, 241–243, 245, 454, 620, venturicidin A 625 690, 700, 789, 879, 893, 894 VerangoTM 1586, 1602–1603, 1642 vermelone 889, 893 u vertebrate UDP‐dependent glycosyltransferases nAChR subunits 1231–1232 (UGTs) 439 subunits 1231, 1456 uncouplers, of oxidative vertebrate γ‐aminobutyric acid phosphorylation 1480 arylhydrazones and very long‐chain fatty acid elongase ferimzone 715–717 (VLCFAE) 377 chemical uncouplers 710–714 very long chain fatty acids (VLCFAs) diarylamines and definition and role of 351 fluazinam 717–719 fatty acid elongation dinitrophenols and basics of 352–353 meptyldinocap 715 FAE‐like condensing mechanism enzymes 353 ATP synthesis 703 phylogenetic analyses 353 bimolecular 705 substrate specificity cell death 703 determination 353–354 ionophores 704 HRAC classification and membrane permeability transition characteristics 359 (MPT) 704 mode of action monomolecular 705 cell division inhibition 355 protonophoric uncouplers 704 modeling 358–359 physicochemical primary targets, history properties 708–710 of 354–355 resistance 707–708 target enzyme 355–357 selectivity and toxicity 706–707 target protein 357–358 uncoupler usnic acid 706 resistance 359–360 uracil heterocycles 184–185, 192, 198 Vespula germanica 1467 ® urban pest control Vivando 939 applications 1466–1467 voltage‐gated calcium channels ureas 266, 411, 529, 549, 1071–1074, (CaV) 1243, 1568 1440, 1535, 1558 voltage‐gated sodium channels (vgSCs) U.S. Environmental Protection Agency and dihydropyrazoles 1433–1435 (EPA) 203, 428, 771, 927, 998, insect 1431–1432 1038, 1063, 1109, 1153, 1249, mammalian 1435–1436 1342, 1381, 1429, 1446, 1587 neurotoxin/insecticide 1433

bindex.indd 1691 12/21/2018 3:11:05 PM 1692 Index

voltage‐gated sodium channels (vgSCs) X‐ray crystallography 248, 504, 613, (contd.) 614, 617, 624, 627, 628, 906, proinsecticide action of 1233, 1237, 1542, 1633 indoxacarb 1432–1433 stages 1432 y ® VotivoTM 1282, 1586, 1605–1606 Yakawide 293 w z water‐dispersible (WG) 68–70, 76, Zea mays 40, 82, 245, 411 1279, 1302, 1414, 1557 ζ‐carotene desaturase 215, 217, 218 Weed resistance 4, 13, 27, 28, 203, zonal Rapporteur Member State 204, 234, 309, 456, 459, 464, 466, (ZRMS) 536 469, 473, 497 zoxamide white‐backed planthopper biology and use in (WBPH) 1286, 1394, 1454 agriculture 793 Widestrike 1111, 1112 competitive binding wild type (WT) 461, 462, 1350, 1351 assays 786–787 Working Group on Pesticides mechanism of action 785–786 (WGP) 533 metabolism and World Health Organization (WHO) 532, toxicology 792–793 914, 996, 1299, 1404 primary markets 785 resistance risk 791–792 x structure–activity Xenopus relationships 789–791 X. laevis 1236, 1405, 1435 synthesis 791 X. oocytes 1249, 1322, 1390, 1453, target‐site‐based resistance, 1454 787–789

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