188:
32:
743:, extracted from East African chrysanthemum flowers and long known to have insecticidal properties. Pyrethrum rapidly knocks down flying insects but has negligible persistence — which is good for the environment but gives poor efficacy when applied in the field. Pyrethroids are essentially chemically stabilized forms of natural pyrethrum and belong to IRAC MoA group 3 (they interfere with sodium transport in insect nerve cells).
20:
609:, populations of bedbugs resistant to both have developed. The use of DDT for this purpose was banned, and its reintroduction would not offer a solution to the problem of bedbugs, due to resistance. Pyrethroids became more commonly used against bedbugs, but resistant populations have now developed to them as well. Populations of
762:, and bioresmethrin. They are more active than the natural pyrethrum but are unstable in sunlight. With the 91/414/EEC review, many 1st-generation compounds have not been included on Annex 1, probably because the market is not big enough to warrant the costs of re-registration (rather than any special concerns about safety).
2074:
Staudinger, H; Ruzicka, L (1924). "Insektentötende Stoffe I. Über
Isolierung und Konstitution des wirksamen Teiles des dalmatinischen Insektenpulvers" [Insecticidal substances I. On isolation and constitution of the active part of the Dalmatian insect powder].
973:
Soderlund, David M; Clark, John M; Sheets, Larry P; Mullin, Linda S; Piccirillo, Vincent J; Sargent, Dana; Stevens, James T; Weiner, Myra L (2002). "Mechanisms of pyrethroid neurotoxicity: Implications for cumulative risk assessment".
1875:
Leibee, Gary L.; Savage, Kenneth E. (1992). "Evaluation of
Selected Insecticides for Control of Diamondback Moth and Cabbage Looper in Cabbage in Central Florida with Observations on Insecticide Resistance in the Diamondback Moth".
1829:
Yoon, Kyong Sup; Kwon, Deok Ho; Strycharz, Joseph P; Hollingsworth, Craig S; Lee, Si Hyeock; Clark, J. Marshall (2008). "Biochemical and
Molecular Analysis of Deltamethrin Resistance in the Common Bed Bug (Hemiptera: Cimicidae)".
522:
It is not well established if chronic exposure to small amounts of pyrethroids is hazardous or not. However, large doses can cause acute poisoning, which is rarely life threatening. Typical symptoms include facial
166:
enzymes which are important in metabolizing the pyrethroid. By that means, the efficacy (lethality) of the pyrethroid is increased. It is likely that there are other mechanisms of intoxication also. Disruption of
527:, itching, burning, dizziness, nausea, vomiting and more severe cases of muscle twitching. Severe poisoning is often caused by ingestion of pyrethroids and can result in a variety of symptoms like seizures,
2113:
2005:
1669:
207:
Pyrethroids are classified based on their mechanism of biological action, as they do not share a common chemical structure. Many are 2,2-dimethylcyclopropanecarboxylic acid derivatives, like
1017:
2105:
1665:
797:. Most patents have now expired, making these compounds cheap and therefore popular (although permethrin and fenvalerate have not been re-registered under the 91/414/EEC process).
1323:
1110:
627:
1919:
519:. They also absorb poorly via skin and human liver is often able to metabolize them relatively efficiently. Pyrethroids are thus much less toxic to humans than to insects.
1978:
3310:
1952:
1628:
685:
597:
The use of pyrethroids as insecticides has led to the development of widespread resistance to them among some insect populations, especially mosquitoes. Although
1266:
785:, but they have significantly higher mammalian toxicities. Over the subsequent decades these derivatives were followed with other proprietary compounds such as
2104:
Haddi, Khalid; Berger, Madeleine; Bielza, Pablo; Cifuentes, Dina; Field, Linda M; Gorman, Kevin; Rapisarda, Carmelo; Williamson, Martin S; Bass, Chris (2012).
1764:
319:, including the resolved isomer alpha-cypermethrin, dichlorovinyl derivative of pyrethrin. Commonly found in crawling insect killers and some mosquito sprays.
1622:
Jeran, Nina; Grdiša, Martina; Varga, Filip; Šatović, Zlatko; Liber, Zlatko; Dabić, Dario; Biošić, Martina (2020-10-06). "Pyrethrin from
Dalmatian pyrethrum (
1574:
Ortiz-Santaliestra ME, et al. (2018). "Validity of fish, birds and mammals as surrogates for amphibians and reptiles in pesticide toxicity assessment".
1216:
Weston, Donald P; Lydy, Michael J (2010). "Urban and
Agricultural Sources of Pyrethroid Insecticides to the Sacramento-San Joaquin Delta of California".
819:
1692:
1812:
2106:"Identification of mutations associated with pyrethroid resistance in the voltage-gated sodium channel of the tomato leaf miner (Tuta absoluta)"
724:
in the 1920s. The pyrethroids represented a major advancement in the chemistry that would synthesize the analog of the natural version found in
334:
2730:
325:, active ingredient of K2000 Insect spray sold in Israel. Mostly used in some aerosols as a Cypermethrin substitute in developing countries.
3135:
2265:
3180:
3074:
2860:
1380:
1378:
Ray, David E.; Ray, Dr David; Forshaw, Philip J. (2000-01-01). "Pyrethroid
Insecticides: Poisoning Syndromes, Synergies, and Therapy".
1973:
2186:
1480:
106:, especially fish. They have been shown to be an effective control measure for malaria outbreaks, through indoor applications.
1558:
1218:
78:
In household concentrations pyrethroids are generally harmless to humans. However, pyrethroids are toxic to insects such as
238:. Pyrethroids that have a common name starting with "cy" have a cyano group and are type II. Fenvalerate also contains an α-
1999:
Dong, Ke; Du, Yuzhe; Rinkevich, Frank; Nomura, Yoshiko; Xu, Peng; Wang, Lingxin; Silver, Kristopher; Zhorov, Boris (2014).
856:
515:
Pyrethroid absorption can happen via skin, inhalation or ingestion. Pyrethroids often do not bind efficiently to mammalian
905:"Prenatal Exposure to DDT and Pyrethroids for Malaria Control and Child Neurodevelopment: The VHEMBE Cohort, South Africa"
563:
more poorly than dogs, which is the cause of this difference. Aside from cats, pyrethroids are typically not toxic to
1344:
909:
227:, which was developed in 1972, is one such example and was the first commercialized pyrethroid without that group.
2532:
1637:
1264:
Bradberry, Sally M.; Cage, Sarah A.; Proudfoot, Alex T.; Vale, J. Allister (2005). "Poisoning due to pyrethroids".
171:
activity is thought to contribute to their irreversible effects on insects, which indicates a pyrethroid action on
1157:"Environmental Modeling and Exposure Assessment of Sediment-Associated Pyrethroids in an Agricultural Watershed"
2527:
1845:
1437:
1011:
Devine, G.J; Denholm, I (2009). "An unconventional use of piperonyl butoxide for managing the cotton whitefly,
836:
61:
781:. They are substantially more resistant to degradation by light and air, thus making them suitable for use in
1832:
495:
and the atmosphere in one or two days, however when associated with sediment they can persist for some time.
172:
3391:
735:
and an unusually fast biodegradation. Their development coincided with the identification of problems with
123:
2680:
1049:
3174:
2487:
2179:
1058:
716:
scientists in the 1960s and 1970s following the elucidation of the structures of pyrethrin I and II by
2150:
1809:
535:. There is an association of pyrethroids with poorer early social-emotional and language development.
3359:
2607:
2502:
2318:
2250:
559:
products, which are intended for dogs, are used on cats. The livers of cats detoxify pyrethroids via
176:
1047:
Soderlund, David M; Bloomquist, Jeffrey R (1989). "Neurotoxic
Actions of Pyrethroid Insecticides".
1626:/Trevir./Sch. Bip.): biosynthesis, biological activity, methods of extraction and determination".
887:
625:. Various mosquito populations have been discovered to have a high level of resistance, including
3352:
2363:
1576:
313:, Temprid, Fumakilla Vape Aerosol, Tempo SC, and many more, dichlorovinyl derivative of pyrethrin
67:
3331:
3291:
2343:
2077:
725:
592:
488:
3345:
2172:
1947:
3386:
2492:
1227:
1170:
976:
721:
668:
637:
499:
8:
3324:
3054:
2650:
2512:
2507:
2323:
2308:
713:
398:
216:
168:
139:
1510:
1475:
1231:
1174:
1066:
3317:
3303:
3199:
3000:
2522:
2517:
2353:
2338:
2300:
2052:
2039:
2000:
1901:
1857:
1791:
1657:
1601:
1550:
1523:
1413:
1355:
1336:
1318:
1299:
1193:
1156:
1132:
1105:
1086:
939:
904:
790:
717:
374:
208:
200:
187:
155:
989:
2855:
2820:
2780:
2328:
2132:
2044:
2026:
1974:"Diamondback Moth - Floriculture and Ornamental Nurseries Pest Management Guidelines"
1893:
1849:
1795:
1783:
1778:
1759:
1740:
1661:
1649:
1593:
1554:
1527:
1515:
1497:
1456:
1405:
1397:
1360:
1340:
1291:
1283:
1279:
1243:
1198:
1137:
1078:
1070:
993:
944:
926:
864:
832:
1861:
1417:
1303:
1090:
502:
facilities. They appear in the effluent, usually at levels lethal to invertebrates.
498:
Pyrethroids are unaffected by conventional secondary treatment systems at municipal
3059:
2790:
2660:
2122:
2086:
2056:
2034:
2018:
1885:
1841:
1773:
1732:
1641:
1605:
1585:
1546:
1505:
1489:
1446:
1389:
1350:
1332:
1275:
1235:
1188:
1178:
1127:
1119:
1062:
1026:
985:
952:
934:
918:
902:
824:
693:
660:
610:
606:
159:
143:
131:
103:
48:
1451:
1432:
613:
have also commonly developed resistance to pyrethroids – including in U.S. states
154:, thereby paralyzing the organism. Pyrethroids can be combined with the synergist
3338:
3257:
2640:
2625:
1816:
1183:
656:
560:
532:
422:
163:
3155:
2635:
2474:
2127:
2022:
1924:
1645:
1493:
739:
use. Their work consisted firstly of identifying the most active components of
701:
556:
516:
262:
151:
147:
1589:
1030:
3380:
3239:
3120:
3064:
3036:
2943:
2933:
2765:
2745:
2411:
2376:
2164:
2090:
2030:
1897:
1653:
1501:
1401:
1287:
1123:
1074:
930:
828:
651:
472:
442:
359:
349:
339:
95:
3282:
3224:
3219:
3125:
3100:
3031:
3026:
2996:
2968:
2923:
2918:
2913:
2898:
2845:
2750:
2720:
2645:
2620:
2582:
2464:
2454:
2439:
2434:
2424:
2401:
2381:
2230:
2195:
2136:
2048:
1853:
1787:
1744:
1597:
1519:
1460:
1409:
1364:
1295:
1247:
1202:
1141:
997:
948:
778:
774:
755:
751:
614:
437:
432:
379:
328:
322:
316:
146:. When the toxin keeps the channels in their open state, the nerves cannot
72:
1736:
1393:
1082:
961:
956:
3297:
3214:
3115:
3105:
3016:
2992:
2983:
2963:
2958:
2948:
2908:
2883:
2865:
2675:
2459:
2429:
2419:
2371:
2348:
2255:
2245:
2199:
2014:
1920:"Pyrethroid Complaints for Diamondback Moth Control in Canola (08/26/21)"
1758:
Kolb, Adam; Needham, Glen R; Neyman, Kimberly M; High, Whitney A (2009).
903:
Brenda
Eskenazi; Sookee An; Stephen A Rauch; et al. (6 April 2018).
786:
782:
632:
524:
460:
417:
403:
369:
354:
266:
254:
239:
224:
220:
135:
115:
83:
31:
3249:
3229:
3160:
3150:
3140:
3130:
3110:
3090:
3021:
3011:
2978:
2973:
2953:
2938:
2928:
2903:
2893:
2888:
2825:
2795:
2735:
2715:
2700:
2695:
2690:
2670:
2592:
2567:
2557:
2449:
2444:
2396:
2386:
2313:
2260:
2240:
2225:
2001:"Molecular biology of insect sodium channels and pyrethroid resistance"
1905:
1677:
794:
770:
759:
646:
622:
427:
408:
394:
384:
364:
344:
306:
285:
249:, also lack the ester bond found in most other pyrethroids and have an
246:
36:
1239:
663:
by Demok et al 2019, and various other locations by Smith et al 2016.
475:, including those that constitute the base of aquatic and terrestrial
98:, including those that constitute the base of aquatic and terrestrial
3195:
3190:
3185:
3170:
3069:
3006:
2988:
2805:
2785:
2775:
2755:
2740:
2655:
2630:
2597:
2497:
2391:
2285:
2275:
2220:
2207:
1819:
U.S. News & World Report 16 July 2007, Vol. 143, Issue 2, p53–54.
740:
618:
580:
476:
468:
388:
279:
99:
91:
56:
52:
24:
1889:
922:
3365:
3267:
3262:
3234:
3209:
3165:
3145:
2850:
2835:
2725:
2710:
2665:
2615:
2552:
2333:
2290:
2270:
2235:
2215:
1161:
732:
681:
492:
464:
127:
87:
1106:"The history of extensive structural modifications of pyrethroids"
3203:
3095:
3046:
2840:
2830:
2810:
2800:
2760:
2685:
2577:
2547:
2060:
598:
576:
258:
230:
Pyrethroids which lack an α-cyano group are often classified as
2815:
2705:
2572:
2562:
2482:
2280:
729:
564:
552:
310:
142:
to pass through the membrane, enter the axon, and propagate an
19:
1828:
2770:
2587:
1693:"DDT repeal would do nothing to combat bed bugs, experts say"
1673:
1476:"Feline permethrin toxicity: retrospective study of 42 cases"
642:
555:
and even death. Poisoning can occur if pyrethroid containing
250:
212:
3272:
2542:
1723:
1042:
1040:
601:
were almost eradicated in North
America through the use of
572:
568:
528:
119:
2103:
1979:
University of
California Agriculture and Natural Resources
1846:
10.1603/0022-2585(2008)45[1092:BAMAOD]2.0.CO;2
1263:
972:
2537:
736:
689:
602:
548:
544:
456:
79:
1037:
1621:
700:
mutations are within or proximate to the two arthropod
261:
atom in the place of the ester. Pyrethroids often have
1319:"Voltage-gated sodium channels as insecticide targets"
479:. They are toxic to aquatic organisms including fish.
2067:
1998:
1757:
138:
interior. This interior is shaped precisely to allow
1543:
Veterinary toxicology: basic and clinical principles
445:, an active ingredient in Baygon and other products.
71:). Pyrethroids are used as commercial and household
1617:
1615:
1046:
551:. Poisoning in cats can result in seizures, fever,
265:and only certain stereoisomers work efficiently as
1573:
2073:
1433:"Pyrethroid epidemiology: a quality-based review"
635:by Chandre et al 1999 through Pwalia et al 2019,
3378:
1612:
857:"Study Links Pesticides to River Contamination"
728:. Its insecticidal activity has relatively low
182:
2194:
1717:Goddard, Jerome; Deshazo, R (2009). "Bed Bugs
1716:
890:from the Illinois Department of Public Health.
820:Ullmann's Encyclopedia of Industrial Chemistry
765:By 1974, the Rothamsted team had discovered a
677:) is one of the stronger kinds of resistance.
2180:
1377:
1010:
257:is also classified as a pyrethroid and has a
1994:
1992:
1990:
1874:
1545:(1st ed.). Elsevier. pp. 676–677.
1473:
1430:
817:Metcalf, Robert L (2000). "Insect Control".
122:. They act by preventing the closure of the
1939:
1721:and Clinical Consequences of Their Bites".
621:while pyrethroids are still recommended in
2187:
2173:
2097:
1381:Journal of Toxicology: Clinical Toxicology
1215:
150:, leaving the axonal membrane permanently
2126:
2114:Insect Biochemistry and Molecular Biology
2038:
2006:Insect Biochemistry and Molecular Biology
1987:
1777:
1509:
1450:
1354:
1192:
1182:
1131:
938:
812:
810:
712:Pyrethroids were introduced by a team of
455:Pyrethroids are toxic to insects such as
1966:
1751:
1710:
1154:
966:
898:
896:
450:
223:ring does not occur in all pyrethroids.
186:
30:
18:
1945:
1912:
1802:
1103:
816:
55:, which are produced by the flowers of
3379:
1691:Craggs, Samantha (November 20, 2014).
1690:
1684:
1670:Phytochemical Society of North America
1481:Journal of Feline Medicine and Surgery
1316:
1219:Environmental Science & Technology
1209:
1004:
883:
881:
854:
807:
769:of more persistent compounds notably:
331:, dibromovinyl derivative of pyrethrin
2168:
2151:"EUR-Lex - 31991L0414 - EN - EUR-Lex"
1540:
1259:
1257:
893:
1155:Luo, Yuzhou; Zhang, Minghua (2011).
850:
848:
1067:10.1146/annurev.en.34.010189.000453
878:
13:
1337:10.1016/B978-0-12-417010-0.00005-7
1254:
1018:Bulletin of Entomological Research
855:Zaveri, Mihir (February 4, 2010).
750:, developed in the 1960s, include
538:
397:(Sumithrin), active ingredient of
282:, the first pyrethroid synthesized
14:
3403:
910:Environmental Health Perspectives
845:
482:
109:
1779:10.1111/j.1529-8019.2009.01246.x
1551:10.1016/B978-012370467-2/50153-X
1280:10.2165/00139709-200524020-00003
391:and most widely used pyrethroid.
2143:
1946:Marsden, Christy (2021-10-15).
1868:
1822:
1666:Phytochemical Society of Europe
1638:Springer Science+Business Media
1567:
1534:
1467:
1424:
1371:
1317:Silver KS, et al. (2014).
1310:
1925:NDSU Agriculture and Extension
1541:Gupta RC, et al. (2007).
1438:Critical Reviews in Toxicology
1148:
1097:
543:Pyrethroids are very toxic to
387:, dichlorovinyl derivative of
173:voltage-gated calcium channels
62:Chrysanthemum cinerariaefolium
1:
1833:Journal of Medical Entomology
1474:Boland, L; Angles, J (2010).
1452:10.1080/10408444.2017.1423463
1431:Burns, C; Pastoor, T (2018).
1324:Advances in Insect Physiology
990:10.1016/s0300-483x(01)00569-8
800:
586:
234:and those with it are called
124:voltage-gated sodium channels
1184:10.1371/journal.pone.0015794
1111:Journal of Pesticide Science
748:first-generation pyrethroids
183:Chemistry and classification
7:
2681:Diisopropyl fluorophosphate
1050:Annual Review of Entomology
1015:(Hemiptera: Aleyrodidae)".
272:
102:. Pyrethroids are toxic to
10:
3408:
2128:10.1016/j.ibmb.2012.03.008
2023:10.1016/j.ibmb.2014.03.012
1646:10.1007/s11101-020-09724-2
1494:10.1016/j.jfms.2009.09.018
707:
659:by Amelia-Yap et al 2018,
649:by Opondo et al 2019, and
590:
571:. They are often toxic to
309:, an active ingredient in
130:. The sodium channel is a
3360:Purpureocillium lilacinum
3281:
3248:
3083:
3045:
2874:
2606:
2473:
2410:
2362:
2319:Chromated copper arsenate
2299:
2251:m-Cumenyl methylcarbamate
2206:
1624:Tanacetum cinerariifolium
1590:10.1007/s10646-018-1911-y
1031:10.1017/S0007485300054262
645:by Ismail et al 2018 and
510:
505:
2364:Insect growth regulators
2091:10.1002/hlca.19240070124
1878:The Florida Entomologist
1124:10.1584/jpestics.D19-102
829:10.1002/14356007.a14_263
487:Pyrethroids are usually
3353:Paenibacillus popilliae
823:. Weinheim: Wiley-VCH.
411:, active ingredient of
288:, active ingredient of
245:Some pyrethroids, like
51:similar to the natural
3332:Metarhizium anisopliae
3311:Beauveria brongniartii
3292:Bacillus thuringiensis
2344:Lead hydrogen arsenate
2078:Helvetica Chimica Acta
1953:Wisconsin Horticulture
1810:"You May not be Alone"
1629:Phytochemistry Reviews
888:Pyrethroids fact sheet
686:target-site resistance
628:Anopheles gambiae s.l.
593:Insecticide resistance
298:Ortho Home Defense Max
204:
177:voltage-gated channels
40:
35:Chemical structure of
28:
23:Chemical structure of
3346:Lecanicillium lecanii
1737:10.1001/jama.2009.405
1394:10.1081/CLT-100100922
1267:Toxicological Reviews
861:The Daily Californian
591:Further information:
451:Environmental effects
190:
34:
22:
16:Class of insecticides
2493:Carbon tetrachloride
1765:Dermatologic Therapy
692:and pyrethroids and
669:Knockdown resistance
500:wastewater treatment
3392:Household chemicals
3325:Metarhizium acridum
3055:Chlorantraniliprole
2651:Chlorpyrifos-methyl
2324:Copper(II) arsenate
2309:Aluminium phosphide
2301:Inorganic compounds
1678:0000-0002-4584-4851
1232:2010EnST...44.1833W
1175:2011PLoSO...615794L
1104:Ujihara, K (2019).
714:Rothamsted Research
253:bond in its place.
236:type II pyrethroids
175:(and perhaps other
3318:Isaria fumosorosea
3304:Beauveria bassiana
3200:Piperonyl butoxide
3001:chrysanthemic acid
2339:Diatomaceous earth
1948:"Diamondback Moth"
1815:2011-11-07 at the
791:lambda-cyhalothrin
718:Hermann Staudinger
375:lambda-Cyhalothrin
232:type I pyrethroids
209:chrysanthemic acid
205:
201:chrysanthemic acid
156:piperonyl butoxide
41:
29:
3374:
3373:
3175:+milbemycin oxime
2856:Tetrachlorvinphos
2821:Pirimiphos-methyl
2781:Oxydemeton-methyl
2329:Copper(I) cyanide
1719:Cimex lectularius
1560:978-0-08-048160-9
1240:10.1021/es9035573
865:Daily Californian
767:second generation
611:Diamondback moths
471:, and some other
104:aquatic organisms
94:, and some other
3399:
3060:Cyantraniliprole
2791:Parathion-methyl
2661:Demeton-S-methyl
2608:Organophosphorus
2189:
2182:
2175:
2166:
2165:
2159:
2158:
2147:
2141:
2140:
2130:
2110:
2101:
2095:
2094:
2071:
2065:
2064:
2042:
1996:
1985:
1984:
1970:
1964:
1963:
1961:
1960:
1943:
1937:
1936:
1934:
1933:
1916:
1910:
1909:
1872:
1866:
1865:
1826:
1820:
1808:Voiland, Adam.
1806:
1800:
1799:
1781:
1755:
1749:
1748:
1714:
1708:
1707:
1705:
1703:
1688:
1682:
1681:
1619:
1610:
1609:
1571:
1565:
1564:
1538:
1532:
1531:
1513:
1471:
1465:
1464:
1454:
1428:
1422:
1421:
1375:
1369:
1368:
1358:
1314:
1308:
1307:
1261:
1252:
1251:
1213:
1207:
1206:
1196:
1186:
1152:
1146:
1145:
1135:
1101:
1095:
1094:
1044:
1035:
1034:
1008:
1002:
1001:
970:
964:
960:
942:
900:
891:
885:
876:
875:
873:
871:
852:
843:
842:
814:
694:cross-resistance
672:
671:
661:Papua New Guinea
607:organophosphates
199:)- or (+)-trans-
144:action potential
132:membrane protein
114:Pyrethroids are
49:organic compound
3407:
3406:
3402:
3401:
3400:
3398:
3397:
3396:
3377:
3376:
3375:
3370:
3339:Nomuraea rileyi
3277:
3244:
3084:Other chemicals
3079:
3041:
2870:
2641:Chlorfenvinphos
2626:Azinphos-methyl
2602:
2475:Organochlorides
2469:
2406:
2358:
2354:Scheele's Green
2295:
2202:
2193:
2163:
2162:
2157:. 15 July 1991.
2149:
2148:
2144:
2108:
2102:
2098:
2072:
2068:
1997:
1988:
1972:
1971:
1967:
1958:
1956:
1944:
1940:
1931:
1929:
1918:
1917:
1913:
1890:10.2307/3496140
1873:
1869:
1840:(6): 1092–101.
1827:
1823:
1817:Wayback Machine
1807:
1803:
1756:
1752:
1731:(13): 1358–66.
1715:
1711:
1701:
1699:
1689:
1685:
1620:
1613:
1572:
1568:
1561:
1539:
1535:
1472:
1468:
1429:
1425:
1376:
1372:
1347:
1315:
1311:
1262:
1255:
1214:
1210:
1153:
1149:
1102:
1098:
1045:
1038:
1009:
1005:
971:
967:
923:10.1289/EHP2129
901:
894:
886:
879:
869:
867:
853:
846:
839:
815:
808:
803:
722:Leopold RuĹľiÄŤka
710:
667:
666:
657:South East Asia
595:
589:
561:glucuronidation
541:
539:Other organisms
533:pulmonary edema
517:sodium channels
513:
508:
485:
453:
448:
423:tau-Fluvalinate
275:
219:. However, the
185:
164:microsomal P450
112:
17:
12:
11:
5:
3405:
3395:
3394:
3389:
3372:
3371:
3369:
3368:
3363:
3356:
3349:
3342:
3335:
3328:
3321:
3314:
3307:
3300:
3295:
3287:
3285:
3279:
3278:
3276:
3275:
3270:
3265:
3260:
3254:
3252:
3246:
3245:
3243:
3242:
3237:
3232:
3227:
3222:
3217:
3212:
3207:
3193:
3188:
3183:
3178:
3168:
3163:
3158:
3156:Hydramethylnon
3153:
3148:
3143:
3138:
3133:
3128:
3123:
3118:
3113:
3108:
3103:
3098:
3093:
3087:
3085:
3081:
3080:
3078:
3077:
3072:
3067:
3062:
3057:
3051:
3049:
3043:
3042:
3040:
3039:
3034:
3029:
3024:
3019:
3014:
3009:
3004:
2986:
2981:
2976:
2971:
2966:
2961:
2956:
2951:
2946:
2941:
2936:
2931:
2926:
2921:
2916:
2911:
2906:
2901:
2896:
2891:
2886:
2880:
2878:
2872:
2871:
2869:
2868:
2863:
2858:
2853:
2848:
2843:
2838:
2833:
2828:
2823:
2818:
2813:
2808:
2803:
2798:
2793:
2788:
2783:
2778:
2773:
2768:
2763:
2758:
2753:
2748:
2743:
2738:
2733:
2728:
2723:
2718:
2713:
2708:
2703:
2698:
2693:
2688:
2683:
2678:
2673:
2668:
2663:
2658:
2653:
2648:
2643:
2638:
2636:Chlorethoxyfos
2633:
2628:
2623:
2618:
2612:
2610:
2604:
2603:
2601:
2600:
2595:
2590:
2585:
2580:
2575:
2570:
2565:
2560:
2555:
2550:
2545:
2540:
2535:
2530:
2525:
2520:
2515:
2510:
2505:
2500:
2495:
2490:
2485:
2479:
2477:
2471:
2470:
2468:
2467:
2462:
2457:
2452:
2447:
2442:
2437:
2432:
2427:
2422:
2416:
2414:
2412:Neonicotinoids
2408:
2407:
2405:
2404:
2399:
2394:
2389:
2384:
2379:
2374:
2368:
2366:
2360:
2359:
2357:
2356:
2351:
2346:
2341:
2336:
2331:
2326:
2321:
2316:
2311:
2305:
2303:
2297:
2296:
2294:
2293:
2288:
2283:
2278:
2273:
2268:
2263:
2258:
2253:
2248:
2243:
2238:
2233:
2228:
2223:
2218:
2212:
2210:
2204:
2203:
2192:
2191:
2184:
2177:
2169:
2161:
2160:
2142:
2096:
2085:(1): 177–201.
2066:
1986:
1965:
1938:
1911:
1867:
1821:
1801:
1750:
1709:
1683:
1611:
1584:(7): 819–833.
1566:
1559:
1533:
1466:
1445:(4): 297–311.
1423:
1370:
1345:
1309:
1253:
1226:(5): 1833–40.
1208:
1147:
1118:(4): 215–224.
1096:
1059:Annual Reviews
1036:
1013:Bemisia tabaci
1003:
965:
892:
877:
844:
837:
805:
804:
802:
799:
709:
706:
702:sodium channel
588:
585:
557:flea treatment
540:
537:
531:, bleeding or
512:
509:
507:
504:
484:
483:Biodegradation
481:
452:
449:
447:
446:
440:
435:
430:
425:
420:
415:
406:
401:
392:
382:
377:
372:
367:
362:
357:
352:
347:
342:
337:
332:
326:
320:
314:
304:
283:
276:
274:
271:
263:chiral centers
184:
181:
179:more widely).
169:neuroendocrine
126:in the axonal
111:
110:Mode of action
108:
15:
9:
6:
4:
3:
2:
3404:
3393:
3390:
3388:
3385:
3384:
3382:
3367:
3364:
3362:
3361:
3357:
3355:
3354:
3350:
3348:
3347:
3343:
3341:
3340:
3336:
3334:
3333:
3329:
3327:
3326:
3322:
3320:
3319:
3315:
3313:
3312:
3308:
3306:
3305:
3301:
3299:
3296:
3294:
3293:
3289:
3288:
3286:
3284:
3283:Biopesticides
3280:
3274:
3271:
3269:
3266:
3264:
3261:
3259:
3256:
3255:
3253:
3251:
3247:
3241:
3240:Metaflumizone
3238:
3236:
3233:
3231:
3228:
3226:
3223:
3221:
3218:
3216:
3213:
3211:
3208:
3205:
3201:
3197:
3194:
3192:
3189:
3187:
3184:
3182:
3179:
3176:
3172:
3169:
3167:
3164:
3162:
3159:
3157:
3154:
3152:
3149:
3147:
3144:
3142:
3139:
3137:
3134:
3132:
3129:
3127:
3124:
3122:
3121:Chlordimeform
3119:
3117:
3114:
3112:
3109:
3107:
3104:
3102:
3099:
3097:
3094:
3092:
3089:
3088:
3086:
3082:
3076:
3073:
3071:
3068:
3066:
3065:Flubendiamide
3063:
3061:
3058:
3056:
3053:
3052:
3050:
3048:
3044:
3038:
3037:Transfluthrin
3035:
3033:
3030:
3028:
3025:
3023:
3020:
3018:
3015:
3013:
3010:
3008:
3005:
3002:
2998:
2994:
2990:
2987:
2985:
2982:
2980:
2977:
2975:
2972:
2970:
2967:
2965:
2962:
2960:
2957:
2955:
2952:
2950:
2947:
2945:
2944:Fenpropathrin
2942:
2940:
2937:
2935:
2934:Esfenvalerate
2932:
2930:
2927:
2925:
2922:
2920:
2917:
2915:
2912:
2910:
2907:
2905:
2902:
2900:
2897:
2895:
2892:
2890:
2887:
2885:
2882:
2881:
2879:
2877:
2873:
2867:
2864:
2862:
2859:
2857:
2854:
2852:
2849:
2847:
2844:
2842:
2839:
2837:
2834:
2832:
2829:
2827:
2824:
2822:
2819:
2817:
2814:
2812:
2809:
2807:
2804:
2802:
2799:
2797:
2794:
2792:
2789:
2787:
2784:
2782:
2779:
2777:
2774:
2772:
2769:
2767:
2766:Monocrotophos
2764:
2762:
2759:
2757:
2754:
2752:
2749:
2747:
2746:Methamidophos
2744:
2742:
2739:
2737:
2734:
2732:
2729:
2727:
2724:
2722:
2719:
2717:
2714:
2712:
2709:
2707:
2704:
2702:
2699:
2697:
2694:
2692:
2689:
2687:
2684:
2682:
2679:
2677:
2674:
2672:
2669:
2667:
2664:
2662:
2659:
2657:
2654:
2652:
2649:
2647:
2644:
2642:
2639:
2637:
2634:
2632:
2629:
2627:
2624:
2622:
2619:
2617:
2614:
2613:
2611:
2609:
2605:
2599:
2596:
2594:
2591:
2589:
2586:
2584:
2581:
2579:
2576:
2574:
2571:
2569:
2566:
2564:
2561:
2559:
2556:
2554:
2551:
2549:
2546:
2544:
2541:
2539:
2536:
2534:
2531:
2529:
2526:
2524:
2521:
2519:
2516:
2514:
2511:
2509:
2506:
2504:
2501:
2499:
2496:
2494:
2491:
2489:
2486:
2484:
2481:
2480:
2478:
2476:
2472:
2466:
2463:
2461:
2458:
2456:
2453:
2451:
2448:
2446:
2443:
2441:
2438:
2436:
2433:
2431:
2428:
2426:
2423:
2421:
2418:
2417:
2415:
2413:
2409:
2403:
2400:
2398:
2395:
2393:
2390:
2388:
2385:
2383:
2380:
2378:
2377:Diflubenzuron
2375:
2373:
2370:
2369:
2367:
2365:
2361:
2355:
2352:
2350:
2347:
2345:
2342:
2340:
2337:
2335:
2332:
2330:
2327:
2325:
2322:
2320:
2317:
2315:
2312:
2310:
2307:
2306:
2304:
2302:
2298:
2292:
2289:
2287:
2284:
2282:
2279:
2277:
2274:
2272:
2269:
2267:
2264:
2262:
2259:
2257:
2254:
2252:
2249:
2247:
2244:
2242:
2239:
2237:
2234:
2232:
2229:
2227:
2224:
2222:
2219:
2217:
2214:
2213:
2211:
2209:
2205:
2201:
2197:
2190:
2185:
2183:
2178:
2176:
2171:
2170:
2167:
2156:
2152:
2146:
2138:
2134:
2129:
2124:
2121:(7): 506–13.
2120:
2116:
2115:
2107:
2100:
2092:
2088:
2084:
2080:
2079:
2070:
2062:
2058:
2054:
2050:
2046:
2041:
2036:
2032:
2028:
2024:
2020:
2016:
2012:
2008:
2007:
2002:
1995:
1993:
1991:
1982:
1980:
1975:
1969:
1955:
1954:
1949:
1942:
1927:
1926:
1921:
1915:
1907:
1903:
1899:
1895:
1891:
1887:
1883:
1879:
1871:
1863:
1859:
1855:
1851:
1847:
1843:
1839:
1835:
1834:
1825:
1818:
1814:
1811:
1805:
1797:
1793:
1789:
1785:
1780:
1775:
1772:(4): 347–52.
1771:
1767:
1766:
1761:
1754:
1746:
1742:
1738:
1734:
1730:
1726:
1725:
1720:
1713:
1698:
1694:
1687:
1679:
1675:
1671:
1667:
1663:
1659:
1655:
1651:
1647:
1643:
1639:
1635:
1631:
1630:
1625:
1618:
1616:
1607:
1603:
1599:
1595:
1591:
1587:
1583:
1579:
1578:
1577:Ecotoxicology
1570:
1562:
1556:
1552:
1548:
1544:
1537:
1529:
1525:
1521:
1517:
1512:
1507:
1503:
1499:
1495:
1491:
1487:
1483:
1482:
1477:
1470:
1462:
1458:
1453:
1448:
1444:
1440:
1439:
1434:
1427:
1419:
1415:
1411:
1407:
1403:
1399:
1395:
1391:
1388:(2): 95–101.
1387:
1383:
1382:
1374:
1366:
1362:
1357:
1352:
1348:
1346:9780124170100
1342:
1338:
1334:
1330:
1326:
1325:
1320:
1313:
1305:
1301:
1297:
1293:
1289:
1285:
1281:
1277:
1274:(2): 93–106.
1273:
1269:
1268:
1260:
1258:
1249:
1245:
1241:
1237:
1233:
1229:
1225:
1221:
1220:
1212:
1204:
1200:
1195:
1190:
1185:
1180:
1176:
1172:
1169:(1): e15794.
1168:
1164:
1163:
1158:
1151:
1143:
1139:
1134:
1129:
1125:
1121:
1117:
1113:
1112:
1107:
1100:
1092:
1088:
1084:
1080:
1076:
1072:
1068:
1064:
1060:
1056:
1052:
1051:
1043:
1041:
1032:
1028:
1025:(6): 601–10.
1024:
1020:
1019:
1014:
1007:
999:
995:
991:
987:
983:
979:
978:
969:
963:
958:
954:
950:
946:
941:
936:
932:
928:
924:
920:
917:(4): 047004.
916:
912:
911:
906:
899:
897:
889:
884:
882:
866:
862:
858:
851:
849:
840:
834:
830:
826:
822:
821:
813:
811:
806:
798:
796:
792:
788:
784:
780:
776:
772:
768:
763:
761:
757:
753:
749:
744:
742:
738:
734:
731:
727:
723:
719:
715:
705:
703:
699:
696:to DDT. Most
695:
691:
687:
683:
680:
676:
670:
664:
662:
658:
654:
653:
652:Aedes aegypti
648:
644:
640:
639:
638:A. arabiensis
634:
630:
629:
624:
620:
616:
612:
608:
604:
600:
594:
584:
582:
578:
574:
570:
566:
562:
558:
554:
550:
547:, but not to
546:
536:
534:
530:
526:
520:
518:
503:
501:
496:
494:
490:
480:
478:
474:
473:invertebrates
470:
466:
462:
458:
444:
443:Transfluthrin
441:
439:
436:
434:
431:
429:
426:
424:
421:
419:
416:
414:
410:
407:
405:
402:
400:
396:
393:
390:
386:
383:
381:
378:
376:
373:
371:
368:
366:
363:
361:
360:Flucythrinate
358:
356:
353:
351:
350:Fenpropathrin
348:
346:
343:
341:
340:Esfenvalerate
338:
336:
333:
330:
327:
324:
321:
318:
315:
312:
308:
305:
303:
299:
295:
291:
287:
284:
281:
278:
277:
270:
268:
264:
260:
256:
252:
248:
243:
241:
237:
233:
228:
226:
222:
218:
214:
210:
202:
198:
194:
189:
180:
178:
174:
170:
165:
161:
157:
153:
149:
145:
141:
137:
133:
129:
125:
121:
117:
107:
105:
101:
97:
96:invertebrates
93:
89:
85:
81:
76:
74:
70:
69:
64:
63:
58:
54:
50:
46:
38:
33:
26:
21:
3358:
3351:
3344:
3337:
3330:
3323:
3316:
3309:
3302:
3290:
3225:Tebufenpyrad
3220:Tebufenozide
3126:Chlorfenapyr
3101:Azadirachtin
3032:Tralomethrin
3027:Tetramethrin
2969:Metofluthrin
2924:Deltamethrin
2919:Cyphenothrin
2914:Cypermethrin
2899:Bioallethrin
2875:
2846:Tebupirimfos
2751:Methidathion
2721:Fenitrothion
2646:Chlorpyrifos
2621:Azamethiphos
2583:Methoxychlor
2465:Thiamethoxam
2455:Paichongding
2440:Imidaclothiz
2435:Imidacloprid
2425:Clothianidin
2402:Pyriproxyfen
2382:Flufenoxuron
2372:Benzoylureas
2231:Butocarboxim
2200:Insecticides
2196:Pest control
2154:
2145:
2118:
2112:
2099:
2082:
2076:
2069:
2010:
2004:
1977:
1968:
1957:. Retrieved
1951:
1941:
1930:. Retrieved
1928:. 2021-08-26
1923:
1914:
1881:
1877:
1870:
1837:
1831:
1824:
1804:
1769:
1763:
1753:
1728:
1722:
1718:
1712:
1700:. Retrieved
1696:
1686:
1633:
1627:
1623:
1581:
1575:
1569:
1542:
1536:
1488:(2): 61–71.
1485:
1479:
1469:
1442:
1436:
1426:
1385:
1379:
1373:
1328:
1322:
1312:
1271:
1265:
1223:
1217:
1211:
1166:
1160:
1150:
1115:
1109:
1099:
1054:
1048:
1022:
1016:
1012:
1006:
981:
975:
968:
914:
908:
868:. Retrieved
860:
818:
779:deltamethrin
775:cypermethrin
766:
764:
756:tetramethrin
752:bioallethrin
747:
745:
711:
697:
678:
674:
665:
650:
636:
626:
615:North Dakota
596:
542:
521:
514:
497:
489:broken apart
486:
454:
438:Tralomethrin
433:Tetramethrin
412:
380:Metofluthrin
335:Dimefluthrin
329:Deltamethrin
323:Cyphenothrin
317:Cypermethrin
301:
297:
293:
289:
267:insecticides
244:
235:
231:
229:
206:
196:
192:
113:
77:
73:insecticides
68:C. coccineum
66:
60:
44:
42:
3387:Pyrethroids
3298:Baculovirus
3250:Metabolites
3215:Sulfluramid
3017:Silafluofen
2984:Prallethrin
2964:Imiprothrin
2959:Fluvalinate
2949:Fenvalerate
2909:Cyhalothrin
2884:Acrinathrin
2876:Pyrethroids
2866:Trichlorfon
2731:Fosthiazate
2676:Dicrotophos
2460:Thiacloprid
2430:Dinotefuran
2420:Acetamiprid
2349:Paris Green
2256:Ethienocarb
2246:Carbosulfan
2015:Elsevier BV
1702:14 November
1640:: 875–905.
1331:: 389–433.
984:(1): 3–59.
787:fenvalerate
783:agriculture
633:West Africa
525:paresthesia
461:dragonflies
418:Silafluofen
404:Prallethrin
370:Imiprothrin
355:Fenvalerate
302:Bifenthrine
255:Silafluofen
240:cyano group
225:Fenvalerate
221:cyclopropyl
152:depolarized
140:sodium ions
136:hydrophilic
116:excitotoxic
84:dragonflies
3381:Categories
3230:Veracevine
3161:Indoxacarb
3151:Fluralaner
3141:Fenoxycarb
3136:Fenazaquin
3131:Cyromazine
3111:Buprofezin
3091:Afoxolaner
3022:Tefluthrin
3012:Resmethrin
2979:Phenothrin
2974:Permethrin
2954:Flumethrin
2939:Etofenprox
2929:Empenthrin
2904:Cyfluthrin
2894:Bifenthrin
2889:Allethrins
2826:Quinalphos
2796:Phenthoate
2736:Isoxathion
2716:Fenamiphos
2701:Disulfoton
2696:Dioxathion
2691:Dimethoate
2671:Dichlorvos
2593:Tetradifon
2568:Heptachlor
2558:Endosulfan
2503:Cyclodiene
2450:Nithiazine
2445:Nitenpyram
2397:Methoprene
2387:Hydroprene
2314:Boric acid
2266:Isoprocarb
2261:Fenobucarb
2241:Carbofuran
2226:Bendiocarb
2208:Carbamates
1959:2022-01-08
1932:2022-01-08
1884:(4): 585.
977:Toxicology
838:3527306730
801:References
795:cyfluthrin
771:permethrin
760:resmethrin
647:The Gambia
623:California
587:Resistance
581:amphibians
428:Tefluthrin
409:Resmethrin
395:Phenothrin
385:Permethrin
365:Flumethrin
345:Etofenprox
307:Cyfluthrin
286:Bifenthrin
247:etofenprox
213:esterified
158:, a known
148:repolarize
57:pyrethrums
53:pyrethrins
45:pyrethroid
37:Permethrin
3196:Adjuvants
3191:Sarolaner
3186:Pyriprole
3181:Pyridaben
3171:Lotilaner
3106:Bensultap
3070:Ryanodine
3007:Pyrethrum
2989:Pyrethrin
2806:Phosalone
2786:Parathion
2776:Omethoate
2756:Mevinphos
2741:Malathion
2656:Coumaphos
2631:Bensulide
2598:Toxaphene
2498:Chlordane
2392:Lufenuron
2286:Promecarb
2276:Metolcarb
2221:Aminocarb
2155:europa.eu
2063:: 582398.
2031:0965-1748
1898:0015-4040
1796:221648188
1760:"Bedbugs"
1662:225152789
1654:1568-7767
1528:206051191
1502:1532-2750
1402:0731-3810
1288:1176-2551
1075:0066-4170
1061:: 77–96.
962:(erratum)
957:Q52880664
931:0091-6765
793:and beta-
741:pyrethrum
730:mammalian
726:pyrethrum
682:mutations
619:Wisconsin
477:food webs
389:pyrethrin
280:Allethrin
160:inhibitor
128:membranes
100:food webs
25:Allethrin
3366:Spinosad
3268:Paraoxon
3263:Malaoxon
3235:Xanthone
3210:Spinosad
3166:Limonene
3146:Fipronil
3075:Ryanodol
3047:Ryanoids
2861:Tribufos
2851:Terbufos
2836:Schradan
2726:Fenthion
2711:Ethoprop
2666:Diazinon
2616:Acephate
2553:Dieldrin
2488:Beta-HCH
2334:Cryolite
2291:Propoxur
2271:Methomyl
2236:Carbaryl
2216:Aldicarb
2137:22504519
2049:24704279
2017:: 1–17.
1862:27422270
1854:19058634
1813:Archived
1788:19580578
1745:19336711
1697:CBC News
1598:29492806
1520:19897392
1511:10911430
1461:29389244
1418:22213256
1410:10778904
1365:29928068
1304:32523158
1296:16180929
1248:20121184
1203:21246035
1162:PLOS ONE
1142:31777441
1091:31881940
998:11812616
953:Wikidata
949:29648420
733:toxicity
577:reptiles
493:sunlight
469:gadflies
465:mayflies
273:Examples
215:with an
92:gadflies
88:mayflies
3204:Sesamex
3096:Amitraz
2841:Temefos
2831:R-16661
2811:Phosmet
2801:Phorate
2761:Mipafox
2686:Dimefox
2578:Lindane
2548:Dicofol
2523:1,2-DCE
2518:1,1-DCE
2513:1,4-DCB
2508:1,2-DCB
2061:NIHMSID
2057:6332754
2040:4484874
1981:(UCANR)
1906:3496140
1606:3604324
1356:6005695
1228:Bibcode
1194:3016336
1171:Bibcode
1133:6861428
1083:2539040
940:6071803
708:History
704:genes.
684:confer
599:bedbugs
565:mammals
413:Scourge
294:Capture
290:Talstar
259:silicon
217:alcohol
134:with a
39:isomers
27:isomers
3116:Cartap
2816:Phoxim
2706:Ethion
2573:Kepone
2563:Endrin
2483:Aldrin
2281:Oxamyl
2135:
2055:
2047:
2037:
2029:
1904:
1896:
1860:
1852:
1794:
1786:
1743:
1660:
1652:
1604:
1596:
1557:
1526:
1518:
1508:
1500:
1459:
1416:
1408:
1400:
1363:
1353:
1343:
1302:
1294:
1286:
1246:
1201:
1191:
1140:
1130:
1089:
1081:
1073:
996:
955:
947:
937:
929:
870:9 June
863:. The
835:
553:ataxia
511:Humans
506:Safety
311:Baygon
300:, and
47:is an
2771:Naled
2588:Mirex
2109:(PDF)
2053:S2CID
1902:JSTOR
1858:S2CID
1792:S2CID
1674:ORCID
1672:. MG
1658:S2CID
1636:(5).
1602:S2CID
1524:S2CID
1414:S2CID
1300:S2CID
1087:S2CID
1057:(1).
643:Sudan
569:birds
399:Anvil
251:ether
120:axons
3273:TCPy
3258:Oxon
2543:DFDT
2133:PMID
2045:PMID
2027:ISSN
1894:ISSN
1850:PMID
1784:PMID
1741:PMID
1724:JAMA
1704:2016
1650:ISSN
1594:PMID
1555:ISBN
1516:PMID
1498:ISSN
1457:PMID
1406:PMID
1398:ISSN
1361:PMID
1341:ISBN
1292:PMID
1284:ISSN
1244:PMID
1199:PMID
1138:PMID
1079:PMID
1071:ISSN
994:PMID
945:PMID
927:ISSN
872:2012
833:ISBN
777:and
746:The
720:and
617:and
605:and
579:and
573:fish
549:dogs
545:cats
529:coma
457:bees
80:bees
65:and
2538:DDT
2533:DDE
2528:DDD
2123:doi
2087:doi
2035:PMC
2019:doi
1886:doi
1842:doi
1774:doi
1733:doi
1729:301
1642:doi
1586:doi
1547:doi
1506:PMC
1490:doi
1447:doi
1390:doi
1351:PMC
1333:doi
1276:doi
1236:doi
1189:PMC
1179:doi
1128:PMC
1120:doi
1063:doi
1027:doi
986:doi
982:171
935:PMC
919:doi
915:126
825:doi
737:DDT
698:kdr
690:DDT
688:to
679:kdr
675:kdr
655:in
641:in
631:in
603:DDT
567:or
491:by
162:of
118:to
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