199:
754:, 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).
43:
31:
620:, 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
773:, 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).
2085:
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].
984:
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".
1886:
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".
1840:
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)".
533:
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
177:
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
538:, 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,
218:
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
1989:
2116:
808:. 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).
1930:
530:. 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.
830:
608:
The use of pyrethroids as insecticides has led to the development of widespread resistance to them among some insect populations, especially mosquitoes. Although
796:, but they have significantly higher mammalian toxicities. Over the subsequent decades these derivatives were followed with other proprietary compounds such as
2115:
Haddi, Khalid; Berger, Madeleine; Bielza, Pablo; Cifuentes, Dina; Field, Linda M; Gorman, Kevin; Rapisarda, Carmelo; Williamson, Martin S; Bass, Chris (2012).
330:, including the resolved isomer alpha-cypermethrin, dichlorovinyl derivative of pyrethrin. Commonly found in crawling insect killers and some mosquito sprays.
1633:
Jeran, Nina; Grdiša, Martina; Varga, Filip; Šatović, Zlatko; Liber, Zlatko; Dabić, Dario; Biošić, Martina (2020-10-06). "Pyrethrin from
Dalmatian pyrethrum (
1585:
Ortiz-Santaliestra ME, et al. (2018). "Validity of fish, birds and mammals as surrogates for amphibians and reptiles in pesticide toxicity assessment".
1391:
1227:
Weston, Donald P; Lydy, Michael J (2010). "Urban and
Agricultural Sources of Pyrethroid Insecticides to the Sacramento-San Joaquin Delta of California".
1703:
1823:
2117:"Identification of mutations associated with pyrethroid resistance in the voltage-gated sodium channel of the tomato leaf miner (Tuta absoluta)"
735:
in the 1920s. The pyrethroids represented a major advancement in the chemistry that would synthesize the analog of the natural version found in
2197:
1491:
1569:
1229:
336:, active ingredient of K2000 Insect spray sold in Israel. Mostly used in some aerosols as a Cypermethrin substitute in developing countries.
1389:
Ray, David E.; Ray, Dr David; Forshaw, Philip J. (2000-01-01). "Pyrethroid
Insecticides: Poisoning Syndromes, Synergies, and Therapy".
1355:
920:
1648:
2543:
1984:
2124:
2016:
117:, especially fish. They have been shown to be an effective control measure for malaria outbreaks, through indoor applications.
2538:
1448:
847:
89:
In household concentrations pyrethroids are generally harmless to humans. However, pyrethroids are toxic to insects such as
72:
1680:
249:. Pyrethroids that have a common name starting with "cy" have a cyano group and are type II. Fenvalerate also contains an α-
2010:
Dong, Ke; Du, Yuzhe; Rinkevich, Frank; Nomura, Yoshiko; Xu, Peng; Wang, Lingxin; Silver, Kristopher; Zhorov, Boris (2014).
867:
526:
Pyrethroid absorption can happen via skin, inhalation or ingestion. Pyrethroids often do not bind efficiently to mammalian
1843:
916:"Prenatal Exposure to DDT and Pyrethroids for Malaria Control and Child Neurodevelopment: The VHEMBE Cohort, South Africa"
183:
3402:
1028:
134:
2691:
1060:
574:
more poorly than dogs, which is the cause of this difference. Aside from cats, pyrethroids are typically not toxic to
1676:
238:, which was developed in 1972, is one such example and was the first commercialized pyrethroid without that group.
3185:
2498:
2190:
1334:
1275:
Bradberry, Sally M.; Cage, Sarah A.; Proudfoot, Alex T.; Vale, J. Allister (2005). "Poisoning due to pyrethroids".
1069:
182:
activity is thought to contribute to their irreversible effects on insects, which indicates a pyrethroid action on
1121:
638:
3370:
2618:
2513:
2329:
2261:
187:
1168:"Environmental Modeling and Exposure Assessment of Sediment-Associated Pyrethroids in an Agricultural Watershed"
1856:
1022:
Devine, G.J; Denholm, I (2009). "An unconventional use of piperonyl butoxide for managing the cotton whitefly,
792:. They are substantially more resistant to degradation by light and air, thus making them suitable for use in
506:
and the atmosphere in one or two days, however when associated with sediment they can persist for some time.
3363:
3321:
2374:
1963:
1639:
1587:
696:
78:
1277:
746:
and an unusually fast biodegradation. Their development coincided with the identification of problems with
3342:
3302:
2354:
2088:
1775:
603:
499:
198:
3356:
2183:
732:
727:
scientists in the 1960s and 1970s following the elucidation of the structures of pyrethrin I and II by
2161:
1820:
546:. There is an association of pyrethroids with poorer early social-emotional and language development.
3397:
2503:
1238:
1181:
987:
679:
648:
570:
products, which are intended for dogs, are used on cats. The livers of cats detoxify pyrethroids via
510:
3335:
3065:
2661:
2523:
2518:
2334:
2319:
1058:
Soderlund, David M; Bloomquist, Jeffrey R (1989). "Neurotoxic
Actions of Pyrethroid Insecticides".
724:
409:
227:
179:
1637:/Trevir./Sch. Bip.): biosynthesis, biological activity, methods of extraction and determination".
898:
636:. Various mosquito populations have been discovered to have a high level of resistance, including
345:
3328:
3314:
3210:
3011:
2741:
2533:
2528:
2349:
2311:
2063:
1912:
1868:
1802:
1668:
1612:
1534:
1424:
1310:
1097:
801:
728:
385:
324:, Temprid, Fumakilla Vape Aerosol, Tempo SC, and many more, dichlorovinyl derivative of pyrethrin
219:
211:
166:
3146:
2364:
2276:
3191:
3085:
2871:
2866:
2831:
2791:
2339:
2143:
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170:
154:
142:
114:
59:
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1827:
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571:
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174:
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2011:
1935:
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567:
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273:
162:
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42:
1000:
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3131:
3075:
3047:
2954:
2944:
2776:
2756:
2422:
2387:
1985:"Diamondback Moth - Floriculture and Ornamental Nurseries Pest Management Guidelines"
1806:
1789:
1770:
1672:
1538:
1290:
736:
662:
483:
453:
370:
360:
350:
106:
17:
1872:
1428:
1314:
1101:
513:
facilities. They appear in the effluent, usually at levels lethal to invertebrates.
509:
Pyrethroids are unaffected by conventional secondary treatment systems at municipal
3293:
3235:
3230:
3136:
3111:
3042:
3037:
3007:
2979:
2934:
2929:
2924:
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448:
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390:
339:
333:
327:
83:
1462:
1443:
624:
have also commonly developed resistance to pyrethroids – including in U.S. states
165:, thereby paralyzing the organism. Pyrethroids can be combined with the synergist
1194:
3308:
3225:
3126:
3116:
3027:
3003:
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2969:
2959:
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277:
265:
250:
235:
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146:
126:
94:
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1504:
750:
use. Their work consisted firstly of identifying the most active components of
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150:
47:
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1085:
941:
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3017:
2999:
2816:
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2641:
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751:
629:
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110:
102:
67:
63:
35:
2147:
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1798:
1755:
1608:
1530:
1471:
1420:
1375:
1306:
1258:
1213:
1152:
1008:
959:
157:. When the toxin keeps the channels in their open state, the nerves cannot
1747:
1404:
1093:
972:
967:
30:
3376:
3278:
3273:
3245:
3220:
3176:
3156:
2861:
2846:
2736:
2721:
2676:
2626:
2563:
2344:
2301:
2281:
2246:
2226:
1931:"Pyrethroid Complaints for Diamondback Moth Control in Canola (08/26/21)"
1769:
Kolb, Adam; Needham, Glen R; Neyman, Kimberly M; High, Whitney A (2009).
1172:
914:
Brenda
Eskenazi; Sookee An; Stephen A Rauch; et al. (6 April 2018).
743:
692:
503:
475:
138:
98:
3214:
3106:
3057:
2851:
2841:
2821:
2811:
2771:
2696:
2588:
2558:
2071:
2012:"Molecular biology of insect sodium channels and pyrethroid resistance"
1916:
1688:
609:
587:
269:
260:, also lack the ester bond found in most other pyrethroids and have an
1250:
674:
by Demok et al 2019, and various other locations by Smith et al 2016.
486:, including those that constitute the base of aquatic and terrestrial
109:, including those that constitute the base of aquatic and terrestrial
2826:
2716:
2583:
2573:
2493:
2291:
1830:
U.S. News & World Report 16 July 2007, Vol. 143, Issue 2, p53–54.
740:
575:
563:
321:
1900:
933:
2781:
2598:
1684:
1117:"The history of extensive structural modifications of pyrethroids"
653:
261:
223:
197:
3283:
2553:
1734:
583:
579:
539:
241:
Pyrethroids which lack an α-cyano group are often classified as
130:
2179:
153:
to pass through the membrane, enter the axon, and propagate an
2548:
747:
700:
613:
559:
555:
467:
90:
1704:"DDT repeal would do nothing to combat bed bugs, experts say"
1487:"Feline permethrin toxicity: retrospective study of 42 cases"
566:
and even death. Poisoning can occur if pyrethroid containing
1053:
1051:
612:
were almost eradicated in North
America through the use of
1990:
University of
California Agriculture and Natural Resources
1857:
10.1603/0022-2585(2008)45[1092:BAMAOD]2.0.CO;2
711:
mutations are within or proximate to the two arthropod
272:
atom in the place of the ester. Pyrethroids often have
1330:"Voltage-gated sodium channels as insecticide targets"
490:. They are toxic to aquatic organisms including fish.
149:
interior. This interior is shaped precisely to allow
1554:
Veterinary toxicology: basic and clinical principles
456:, an active ingredient in Baygon and other products.
82:). Pyrethroids are used as commercial and household
3292:
3259:
3094:
3056:
2885:
2617:
2484:
2421:
2373:
2310:
2217:
1628:
1626:
562:. Poisoning in cats can result in seizures, fever,
276:and only certain stereoisomers work efficiently as
1444:"Pyrethroid epidemiology: a quality-based review"
646:by Chandre et al 1999 through Pwalia et al 2019,
868:"Study Links Pesticides to River Contamination"
739:. Its insecticidal activity has relatively low
1728:Goddard, Jerome; Deshazo, R (2009). "Bed Bugs
901:from the Illinois Department of Public Health.
831:Ullmann's Encyclopedia of Industrial Chemistry
776:By 1974, the Rothamsted team had discovered a
688:) is one of the stronger kinds of resistance.
2191:
268:is also classified as a pyrethroid and has a
8:
2005:
2003:
2001:
1556:(1st ed.). Elsevier. pp. 676–677.
828:Metcalf, Robert L (2000). "Insect Control".
133:. They act by preventing the closure of the
1732:and Clinical Consequences of Their Bites".
632:while pyrethroids are still recommended in
2198:
2184:
2176:
1392:Journal of Toxicology: Clinical Toxicology
161:, leaving the axonal membrane permanently
2137:
2125:Insect Biochemistry and Molecular Biology
2049:
2017:Insect Biochemistry and Molecular Biology
1788:
1520:
1461:
1365:
1203:
1193:
1142:
949:
823:
821:
723:Pyrethroids were introduced by a team of
466:Pyrethroids are toxic to insects such as
909:
907:
234:ring does not occur in all pyrethroids.
41:
29:
817:
66:, which are produced by the flowers of
1702:Craggs, Samantha (November 20, 2014).
1681:Phytochemical Society of North America
1492:Journal of Feline Medicine and Surgery
1230:Environmental Science & Technology
894:
892:
780:of more persistent compounds notably:
342:, dibromovinyl derivative of pyrethrin
2162:"EUR-Lex - 31991L0414 - EN - EUR-Lex"
1270:
1268:
7:
1166:Luo, Yuzhou; Zhang, Minghua (2011).
861:
859:
1078:10.1146/annurev.en.34.010189.000453
1348:10.1016/B978-0-12-417010-0.00005-7
1029:Bulletin of Entomological Research
866:Zaveri, Mihir (February 4, 2010).
761:, developed in the 1960s, include
408:(Sumithrin), active ingredient of
293:, the first pyrethroid synthesized
25:
921:Environmental Health Perspectives
1790:10.1111/j.1529-8019.2009.01246.x
1562:10.1016/B978-012370467-2/50153-X
1291:10.2165/00139709-200524020-00003
402:and most widely used pyrethroid.
1957:Marsden, Christy (2021-10-15).
1677:Phytochemical Society of Europe
1649:Springer Science+Business Media
1328:Silver KS, et al. (2014).
1936:NDSU Agriculture and Extension
1552:Gupta RC, et al. (2007).
1449:Critical Reviews in Toxicology
554:Pyrethroids are very toxic to
398:, dichlorovinyl derivative of
184:voltage-gated calcium channels
73:Chrysanthemum cinerariaefolium
1:
1844:Journal of Medical Entomology
1485:Boland, L; Angles, J (2010).
1463:10.1080/10408444.2017.1423463
1442:Burns, C; Pastoor, T (2018).
1335:Advances in Insect Physiology
1001:10.1016/s0300-483x(01)00569-8
245:and those with it are called
135:voltage-gated sodium channels
1195:10.1371/journal.pone.0015794
1122:Journal of Pesticide Science
759:first-generation pyrethroids
194:Chemistry and classification
2692:Diisopropyl fluorophosphate
1061:Annual Review of Entomology
1026:(Hemiptera: Aleyrodidae)".
113:. Pyrethroids are toxic to
3419:
2139:10.1016/j.ibmb.2012.03.008
2034:10.1016/j.ibmb.2014.03.012
1657:10.1007/s11101-020-09724-2
1505:10.1016/j.jfms.2009.09.018
670:by Amelia-Yap et al 2018,
660:by Opondo et al 2019, and
601:
582:. They are often toxic to
320:, an active ingredient in
141:. The sodium channel is a
3371:Purpureocillium lilacinum
2330:Chromated copper arsenate
2262:m-Cumenyl methylcarbamate
1635:Tanacetum cinerariifolium
1601:10.1007/s10646-018-1911-y
1042:10.1017/S0007485300054262
656:by Ismail et al 2018 and
2375:Insect growth regulators
2102:10.1002/hlca.19240070124
1889:The Florida Entomologist
1135:10.1584/jpestics.D19-102
840:10.1002/14356007.a14_263
498:Pyrethroids are usually
3364:Paenibacillus popilliae
834:. Weinheim: Wiley-VCH.
422:, active ingredient of
299:, active ingredient of
256:Some pyrethroids, like
62:similar to the natural
3343:Metarhizium anisopliae
3322:Beauveria brongniartii
3303:Bacillus thuringiensis
2355:Lead hydrogen arsenate
2089:Helvetica Chimica Acta
1964:Wisconsin Horticulture
1821:"You May not be Alone"
1640:Phytochemistry Reviews
899:Pyrethroids fact sheet
697:target-site resistance
639:Anopheles gambiae s.l.
604:Insecticide resistance
309:Ortho Home Defense Max
215:
188:voltage-gated channels
51:
46:Chemical structure of
39:
34:Chemical structure of
3357:Lecanicillium lecanii
1748:10.1001/jama.2009.405
1405:10.1081/CLT-100100922
1278:Toxicological Reviews
872:The Daily Californian
602:Further information:
462:Environmental effects
201:
45:
33:
27:Class of insecticides
18:Pyrethroid resistance
2504:Carbon tetrachloride
1776:Dermatologic Therapy
703:and pyrethroids and
680:Knockdown resistance
511:wastewater treatment
3403:Household chemicals
3336:Metarhizium acridum
3066:Chlorantraniliprole
2662:Chlorpyrifos-methyl
2335:Copper(II) arsenate
2320:Aluminium phosphide
2312:Inorganic compounds
1689:0000-0002-4584-4851
1243:2010EnST...44.1833W
1186:2011PLoSO...615794L
1115:Ujihara, K (2019).
725:Rothamsted Research
264:bond in its place.
247:type II pyrethroids
186:(and perhaps other
3329:Isaria fumosorosea
3315:Beauveria bassiana
3211:Piperonyl butoxide
3012:chrysanthemic acid
2350:Diatomaceous earth
1959:"Diamondback Moth"
1826:2011-11-07 at the
802:lambda-cyhalothrin
729:Hermann Staudinger
386:lambda-Cyhalothrin
243:type I pyrethroids
220:chrysanthemic acid
216:
212:chrysanthemic acid
167:piperonyl butoxide
52:
40:
3385:
3384:
3186:+milbemycin oxime
2867:Tetrachlorvinphos
2832:Pirimiphos-methyl
2792:Oxydemeton-methyl
2340:Copper(I) cyanide
1730:Cimex lectularius
1571:978-0-08-048160-9
1251:10.1021/es9035573
876:Daily Californian
778:second generation
622:Diamondback moths
482:, and some other
115:aquatic organisms
105:, and some other
16:(Redirected from
3410:
3071:Cyantraniliprole
2802:Parathion-methyl
2672:Demeton-S-methyl
2619:Organophosphorus
2200:
2193:
2186:
2177:
2170:
2169:
2158:
2152:
2151:
2141:
2121:
2112:
2106:
2105:
2082:
2076:
2075:
2053:
2007:
1996:
1995:
1981:
1975:
1974:
1972:
1971:
1954:
1948:
1947:
1945:
1944:
1927:
1921:
1920:
1883:
1877:
1876:
1837:
1831:
1819:Voiland, Adam.
1817:
1811:
1810:
1792:
1766:
1760:
1759:
1725:
1719:
1718:
1716:
1714:
1699:
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1433:
1432:
1386:
1380:
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1325:
1319:
1318:
1272:
1263:
1262:
1224:
1218:
1217:
1207:
1197:
1163:
1157:
1156:
1146:
1112:
1106:
1105:
1055:
1046:
1045:
1019:
1013:
1012:
981:
975:
971:
953:
911:
902:
896:
887:
886:
884:
882:
863:
854:
853:
825:
705:cross-resistance
683:
682:
672:Papua New Guinea
618:organophosphates
210:)- or (+)-trans-
155:action potential
143:membrane protein
125:Pyrethroids are
60:organic compound
21:
3418:
3417:
3413:
3412:
3411:
3409:
3408:
3407:
3388:
3387:
3386:
3381:
3350:Nomuraea rileyi
3288:
3255:
3095:Other chemicals
3090:
3052:
2881:
2652:Chlorfenvinphos
2637:Azinphos-methyl
2613:
2486:Organochlorides
2480:
2417:
2369:
2365:Scheele's Green
2306:
2213:
2204:
2174:
2173:
2168:. 15 July 1991.
2160:
2159:
2155:
2119:
2114:
2113:
2109:
2084:
2083:
2079:
2009:
2008:
1999:
1983:
1982:
1978:
1969:
1967:
1956:
1955:
1951:
1942:
1940:
1929:
1928:
1924:
1901:10.2307/3496140
1885:
1884:
1880:
1851:(6): 1092–101.
1839:
1838:
1834:
1828:Wayback Machine
1818:
1814:
1768:
1767:
1763:
1742:(13): 1358–66.
1727:
1726:
1722:
1712:
1710:
1701:
1700:
1696:
1632:
1631:
1624:
1584:
1583:
1579:
1572:
1551:
1550:
1546:
1484:
1483:
1479:
1441:
1440:
1436:
1388:
1387:
1383:
1358:
1327:
1326:
1322:
1274:
1273:
1266:
1226:
1225:
1221:
1165:
1164:
1160:
1114:
1113:
1109:
1057:
1056:
1049:
1021:
1020:
1016:
983:
982:
978:
934:10.1289/EHP2129
913:
912:
905:
897:
890:
880:
878:
865:
864:
857:
850:
827:
826:
819:
814:
733:Leopold RuĹľiÄŤka
721:
678:
677:
668:South East Asia
606:
600:
572:glucuronidation
552:
550:Other organisms
544:pulmonary edema
528:sodium channels
524:
519:
496:
464:
459:
434:tau-Fluvalinate
286:
230:. However, the
196:
175:microsomal P450
123:
28:
23:
22:
15:
12:
11:
5:
3416:
3414:
3406:
3405:
3400:
3390:
3389:
3383:
3382:
3380:
3379:
3374:
3367:
3360:
3353:
3346:
3339:
3332:
3325:
3318:
3311:
3306:
3298:
3296:
3290:
3289:
3287:
3286:
3281:
3276:
3271:
3265:
3263:
3257:
3256:
3254:
3253:
3248:
3243:
3238:
3233:
3228:
3223:
3218:
3204:
3199:
3194:
3189:
3179:
3174:
3169:
3167:Hydramethylnon
3164:
3159:
3154:
3149:
3144:
3139:
3134:
3129:
3124:
3119:
3114:
3109:
3104:
3098:
3096:
3092:
3091:
3089:
3088:
3083:
3078:
3073:
3068:
3062:
3060:
3054:
3053:
3051:
3050:
3045:
3040:
3035:
3030:
3025:
3020:
3015:
2997:
2992:
2987:
2982:
2977:
2972:
2967:
2962:
2957:
2952:
2947:
2942:
2937:
2932:
2927:
2922:
2917:
2912:
2907:
2902:
2897:
2891:
2889:
2883:
2882:
2880:
2879:
2874:
2869:
2864:
2859:
2854:
2849:
2844:
2839:
2834:
2829:
2824:
2819:
2814:
2809:
2804:
2799:
2794:
2789:
2784:
2779:
2774:
2769:
2764:
2759:
2754:
2749:
2744:
2739:
2734:
2729:
2724:
2719:
2714:
2709:
2704:
2699:
2694:
2689:
2684:
2679:
2674:
2669:
2664:
2659:
2654:
2649:
2647:Chlorethoxyfos
2644:
2639:
2634:
2629:
2623:
2621:
2615:
2614:
2612:
2611:
2606:
2601:
2596:
2591:
2586:
2581:
2576:
2571:
2566:
2561:
2556:
2551:
2546:
2541:
2536:
2531:
2526:
2521:
2516:
2511:
2506:
2501:
2496:
2490:
2488:
2482:
2481:
2479:
2478:
2473:
2468:
2463:
2458:
2453:
2448:
2443:
2438:
2433:
2427:
2425:
2423:Neonicotinoids
2419:
2418:
2416:
2415:
2410:
2405:
2400:
2395:
2390:
2385:
2379:
2377:
2371:
2370:
2368:
2367:
2362:
2357:
2352:
2347:
2342:
2337:
2332:
2327:
2322:
2316:
2314:
2308:
2307:
2305:
2304:
2299:
2294:
2289:
2284:
2279:
2274:
2269:
2264:
2259:
2254:
2249:
2244:
2239:
2234:
2229:
2223:
2221:
2215:
2214:
2205:
2203:
2202:
2195:
2188:
2180:
2172:
2171:
2153:
2107:
2096:(1): 177–201.
2077:
1997:
1976:
1949:
1922:
1878:
1832:
1812:
1761:
1720:
1694:
1622:
1595:(7): 819–833.
1577:
1570:
1544:
1477:
1456:(4): 297–311.
1434:
1381:
1356:
1320:
1264:
1237:(5): 1833–40.
1219:
1158:
1129:(4): 215–224.
1107:
1070:Annual Reviews
1047:
1024:Bemisia tabaci
1014:
976:
903:
888:
855:
848:
816:
815:
813:
810:
720:
717:
713:sodium channel
599:
596:
568:flea treatment
551:
548:
542:, bleeding or
523:
520:
518:
515:
495:
494:Biodegradation
492:
463:
460:
458:
457:
451:
446:
441:
436:
431:
426:
417:
412:
403:
393:
388:
383:
378:
373:
368:
363:
358:
353:
348:
343:
337:
331:
325:
315:
294:
287:
285:
282:
274:chiral centers
195:
192:
190:more widely).
180:neuroendocrine
137:in the axonal
122:
121:Mode of action
119:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3415:
3404:
3401:
3399:
3396:
3395:
3393:
3378:
3375:
3373:
3372:
3368:
3366:
3365:
3361:
3359:
3358:
3354:
3352:
3351:
3347:
3345:
3344:
3340:
3338:
3337:
3333:
3331:
3330:
3326:
3324:
3323:
3319:
3317:
3316:
3312:
3310:
3307:
3305:
3304:
3300:
3299:
3297:
3295:
3294:Biopesticides
3291:
3285:
3282:
3280:
3277:
3275:
3272:
3270:
3267:
3266:
3264:
3262:
3258:
3252:
3251:Metaflumizone
3249:
3247:
3244:
3242:
3239:
3237:
3234:
3232:
3229:
3227:
3224:
3222:
3219:
3216:
3212:
3208:
3205:
3203:
3200:
3198:
3195:
3193:
3190:
3187:
3183:
3180:
3178:
3175:
3173:
3170:
3168:
3165:
3163:
3160:
3158:
3155:
3153:
3150:
3148:
3145:
3143:
3140:
3138:
3135:
3133:
3132:Chlordimeform
3130:
3128:
3125:
3123:
3120:
3118:
3115:
3113:
3110:
3108:
3105:
3103:
3100:
3099:
3097:
3093:
3087:
3084:
3082:
3079:
3077:
3076:Flubendiamide
3074:
3072:
3069:
3067:
3064:
3063:
3061:
3059:
3055:
3049:
3048:Transfluthrin
3046:
3044:
3041:
3039:
3036:
3034:
3031:
3029:
3026:
3024:
3021:
3019:
3016:
3013:
3009:
3005:
3001:
2998:
2996:
2993:
2991:
2988:
2986:
2983:
2981:
2978:
2976:
2973:
2971:
2968:
2966:
2963:
2961:
2958:
2956:
2955:Fenpropathrin
2953:
2951:
2948:
2946:
2945:Esfenvalerate
2943:
2941:
2938:
2936:
2933:
2931:
2928:
2926:
2923:
2921:
2918:
2916:
2913:
2911:
2908:
2906:
2903:
2901:
2898:
2896:
2893:
2892:
2890:
2888:
2884:
2878:
2875:
2873:
2870:
2868:
2865:
2863:
2860:
2858:
2855:
2853:
2850:
2848:
2845:
2843:
2840:
2838:
2835:
2833:
2830:
2828:
2825:
2823:
2820:
2818:
2815:
2813:
2810:
2808:
2805:
2803:
2800:
2798:
2795:
2793:
2790:
2788:
2785:
2783:
2780:
2778:
2777:Monocrotophos
2775:
2773:
2770:
2768:
2765:
2763:
2760:
2758:
2757:Methamidophos
2755:
2753:
2750:
2748:
2745:
2743:
2740:
2738:
2735:
2733:
2730:
2728:
2725:
2723:
2720:
2718:
2715:
2713:
2710:
2708:
2705:
2703:
2700:
2698:
2695:
2693:
2690:
2688:
2685:
2683:
2680:
2678:
2675:
2673:
2670:
2668:
2665:
2663:
2660:
2658:
2655:
2653:
2650:
2648:
2645:
2643:
2640:
2638:
2635:
2633:
2630:
2628:
2625:
2624:
2622:
2620:
2616:
2610:
2607:
2605:
2602:
2600:
2597:
2595:
2592:
2590:
2587:
2585:
2582:
2580:
2577:
2575:
2572:
2570:
2567:
2565:
2562:
2560:
2557:
2555:
2552:
2550:
2547:
2545:
2542:
2540:
2537:
2535:
2532:
2530:
2527:
2525:
2522:
2520:
2517:
2515:
2512:
2510:
2507:
2505:
2502:
2500:
2497:
2495:
2492:
2491:
2489:
2487:
2483:
2477:
2474:
2472:
2469:
2467:
2464:
2462:
2459:
2457:
2454:
2452:
2449:
2447:
2444:
2442:
2439:
2437:
2434:
2432:
2429:
2428:
2426:
2424:
2420:
2414:
2411:
2409:
2406:
2404:
2401:
2399:
2396:
2394:
2391:
2389:
2388:Diflubenzuron
2386:
2384:
2381:
2380:
2378:
2376:
2372:
2366:
2363:
2361:
2358:
2356:
2353:
2351:
2348:
2346:
2343:
2341:
2338:
2336:
2333:
2331:
2328:
2326:
2323:
2321:
2318:
2317:
2315:
2313:
2309:
2303:
2300:
2298:
2295:
2293:
2290:
2288:
2285:
2283:
2280:
2278:
2275:
2273:
2270:
2268:
2265:
2263:
2260:
2258:
2255:
2253:
2250:
2248:
2245:
2243:
2240:
2238:
2235:
2233:
2230:
2228:
2225:
2224:
2222:
2220:
2216:
2212:
2208:
2201:
2196:
2194:
2189:
2187:
2182:
2181:
2178:
2167:
2163:
2157:
2154:
2149:
2145:
2140:
2135:
2132:(7): 506–13.
2131:
2127:
2126:
2118:
2111:
2108:
2103:
2099:
2095:
2091:
2090:
2081:
2078:
2073:
2069:
2065:
2061:
2057:
2052:
2047:
2043:
2039:
2035:
2031:
2027:
2023:
2019:
2018:
2013:
2006:
2004:
2002:
1998:
1993:
1991:
1986:
1980:
1977:
1966:
1965:
1960:
1953:
1950:
1938:
1937:
1932:
1926:
1923:
1918:
1914:
1910:
1906:
1902:
1898:
1894:
1890:
1882:
1879:
1874:
1870:
1866:
1862:
1858:
1854:
1850:
1846:
1845:
1836:
1833:
1829:
1825:
1822:
1816:
1813:
1808:
1804:
1800:
1796:
1791:
1786:
1783:(4): 347–52.
1782:
1778:
1777:
1772:
1765:
1762:
1757:
1753:
1749:
1745:
1741:
1737:
1736:
1731:
1724:
1721:
1709:
1705:
1698:
1695:
1690:
1686:
1682:
1678:
1674:
1670:
1666:
1662:
1658:
1654:
1650:
1646:
1642:
1641:
1636:
1629:
1627:
1623:
1618:
1614:
1610:
1606:
1602:
1598:
1594:
1590:
1589:
1588:Ecotoxicology
1581:
1578:
1573:
1567:
1563:
1559:
1555:
1548:
1545:
1540:
1536:
1532:
1528:
1523:
1518:
1514:
1510:
1506:
1502:
1498:
1494:
1493:
1488:
1481:
1478:
1473:
1469:
1464:
1459:
1455:
1451:
1450:
1445:
1438:
1435:
1430:
1426:
1422:
1418:
1414:
1410:
1406:
1402:
1399:(2): 95–101.
1398:
1394:
1393:
1385:
1382:
1377:
1373:
1368:
1363:
1359:
1357:9780124170100
1353:
1349:
1345:
1341:
1337:
1336:
1331:
1324:
1321:
1316:
1312:
1308:
1304:
1300:
1296:
1292:
1288:
1285:(2): 93–106.
1284:
1280:
1279:
1271:
1269:
1265:
1260:
1256:
1252:
1248:
1244:
1240:
1236:
1232:
1231:
1223:
1220:
1215:
1211:
1206:
1201:
1196:
1191:
1187:
1183:
1180:(1): e15794.
1179:
1175:
1174:
1169:
1162:
1159:
1154:
1150:
1145:
1140:
1136:
1132:
1128:
1124:
1123:
1118:
1111:
1108:
1103:
1099:
1095:
1091:
1087:
1083:
1079:
1075:
1071:
1067:
1063:
1062:
1054:
1052:
1048:
1043:
1039:
1036:(6): 601–10.
1035:
1031:
1030:
1025:
1018:
1015:
1010:
1006:
1002:
998:
994:
990:
989:
980:
977:
974:
969:
965:
961:
957:
952:
947:
943:
939:
935:
931:
928:(4): 047004.
927:
923:
922:
917:
910:
908:
904:
900:
895:
893:
889:
877:
873:
869:
862:
860:
856:
851:
845:
841:
837:
833:
832:
824:
822:
818:
811:
809:
807:
803:
799:
795:
791:
787:
783:
779:
774:
772:
768:
764:
760:
755:
753:
749:
745:
742:
738:
734:
730:
726:
718:
716:
714:
710:
707:to DDT. Most
706:
702:
698:
694:
691:
687:
681:
675:
673:
669:
665:
664:
663:Aedes aegypti
659:
655:
651:
650:
649:A. arabiensis
645:
641:
640:
635:
631:
627:
623:
619:
615:
611:
605:
597:
595:
593:
589:
585:
581:
577:
573:
569:
565:
561:
558:, but not to
557:
549:
547:
545:
541:
537:
531:
529:
521:
516:
514:
512:
507:
505:
501:
493:
491:
489:
485:
484:invertebrates
481:
477:
473:
469:
461:
455:
454:Transfluthrin
452:
450:
447:
445:
442:
440:
437:
435:
432:
430:
427:
425:
421:
418:
416:
413:
411:
407:
404:
401:
397:
394:
392:
389:
387:
384:
382:
379:
377:
374:
372:
371:Flucythrinate
369:
367:
364:
362:
361:Fenpropathrin
359:
357:
354:
352:
351:Esfenvalerate
349:
347:
344:
341:
338:
335:
332:
329:
326:
323:
319:
316:
314:
310:
306:
302:
298:
295:
292:
289:
288:
283:
281:
279:
275:
271:
267:
263:
259:
254:
252:
248:
244:
239:
237:
233:
229:
225:
221:
213:
209:
205:
200:
193:
191:
189:
185:
181:
176:
172:
168:
164:
160:
156:
152:
148:
144:
140:
136:
132:
128:
120:
118:
116:
112:
108:
107:invertebrates
104:
100:
96:
92:
87:
85:
81:
80:
75:
74:
69:
65:
61:
57:
49:
44:
37:
32:
19:
3369:
3362:
3355:
3348:
3341:
3334:
3327:
3320:
3313:
3301:
3236:Tebufenpyrad
3231:Tebufenozide
3137:Chlorfenapyr
3112:Azadirachtin
3043:Tralomethrin
3038:Tetramethrin
2980:Metofluthrin
2935:Deltamethrin
2930:Cyphenothrin
2925:Cypermethrin
2910:Bioallethrin
2886:
2857:Tebupirimfos
2762:Methidathion
2732:Fenitrothion
2657:Chlorpyrifos
2632:Azamethiphos
2594:Methoxychlor
2476:Thiamethoxam
2466:Paichongding
2451:Imidaclothiz
2446:Imidacloprid
2436:Clothianidin
2413:Pyriproxyfen
2393:Flufenoxuron
2383:Benzoylureas
2242:Butocarboxim
2211:Insecticides
2207:Pest control
2165:
2156:
2129:
2123:
2110:
2093:
2087:
2080:
2021:
2015:
1988:
1979:
1968:. Retrieved
1962:
1952:
1941:. Retrieved
1939:. 2021-08-26
1934:
1925:
1892:
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1848:
1842:
1835:
1815:
1780:
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1764:
1739:
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1729:
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1711:. Retrieved
1707:
1697:
1644:
1638:
1634:
1592:
1586:
1580:
1553:
1547:
1499:(2): 61–71.
1496:
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1033:
1027:
1023:
1017:
992:
986:
979:
925:
919:
879:. Retrieved
871:
829:
790:deltamethrin
786:cypermethrin
777:
775:
767:tetramethrin
763:bioallethrin
758:
756:
722:
708:
689:
685:
676:
661:
647:
637:
626:North Dakota
607:
553:
532:
525:
508:
500:broken apart
497:
465:
449:Tralomethrin
444:Tetramethrin
423:
391:Metofluthrin
346:Dimefluthrin
340:Deltamethrin
334:Cyphenothrin
328:Cypermethrin
312:
308:
304:
300:
278:insecticides
255:
246:
242:
240:
217:
207:
203:
124:
88:
84:insecticides
79:C. coccineum
77:
71:
55:
53:
3398:Pyrethroids
3309:Baculovirus
3261:Metabolites
3226:Sulfluramid
3028:Silafluofen
2995:Prallethrin
2975:Imiprothrin
2970:Fluvalinate
2960:Fenvalerate
2920:Cyhalothrin
2895:Acrinathrin
2887:Pyrethroids
2877:Trichlorfon
2742:Fosthiazate
2687:Dicrotophos
2471:Thiacloprid
2441:Dinotefuran
2431:Acetamiprid
2360:Paris Green
2267:Ethienocarb
2257:Carbosulfan
2026:Elsevier BV
1713:14 November
1651:: 875–905.
1342:: 389–433.
995:(1): 3–59.
798:fenvalerate
794:agriculture
644:West Africa
536:paresthesia
472:dragonflies
429:Silafluofen
415:Prallethrin
381:Imiprothrin
366:Fenvalerate
313:Bifenthrine
266:Silafluofen
251:cyano group
236:Fenvalerate
232:cyclopropyl
163:depolarized
151:sodium ions
147:hydrophilic
127:excitotoxic
95:dragonflies
3392:Categories
3241:Veracevine
3172:Indoxacarb
3162:Fluralaner
3152:Fenoxycarb
3147:Fenazaquin
3142:Cyromazine
3122:Buprofezin
3102:Afoxolaner
3033:Tefluthrin
3023:Resmethrin
2990:Phenothrin
2985:Permethrin
2965:Flumethrin
2950:Etofenprox
2940:Empenthrin
2915:Cyfluthrin
2905:Bifenthrin
2900:Allethrins
2837:Quinalphos
2807:Phenthoate
2747:Isoxathion
2727:Fenamiphos
2712:Disulfoton
2707:Dioxathion
2702:Dimethoate
2682:Dichlorvos
2604:Tetradifon
2579:Heptachlor
2569:Endosulfan
2514:Cyclodiene
2461:Nithiazine
2456:Nitenpyram
2408:Methoprene
2398:Hydroprene
2325:Boric acid
2277:Isoprocarb
2272:Fenobucarb
2252:Carbofuran
2237:Bendiocarb
2219:Carbamates
1970:2022-01-08
1943:2022-01-08
1895:(4): 585.
988:Toxicology
849:3527306730
812:References
806:cyfluthrin
782:permethrin
771:resmethrin
658:The Gambia
634:California
598:Resistance
592:amphibians
439:Tefluthrin
420:Resmethrin
406:Phenothrin
396:Permethrin
376:Flumethrin
356:Etofenprox
318:Cyfluthrin
297:Bifenthrin
258:etofenprox
224:esterified
169:, a known
159:repolarize
68:pyrethrums
64:pyrethrins
56:pyrethroid
48:Permethrin
3207:Adjuvants
3202:Sarolaner
3197:Pyriprole
3192:Pyridaben
3182:Lotilaner
3117:Bensultap
3081:Ryanodine
3018:Pyrethrum
3000:Pyrethrin
2817:Phosalone
2797:Parathion
2787:Omethoate
2767:Mevinphos
2752:Malathion
2667:Coumaphos
2642:Bensulide
2609:Toxaphene
2509:Chlordane
2403:Lufenuron
2297:Promecarb
2287:Metolcarb
2232:Aminocarb
2166:europa.eu
2074:: 582398.
2042:0965-1748
1909:0015-4040
1807:221648188
1771:"Bedbugs"
1673:225152789
1665:1568-7767
1539:206051191
1513:1532-2750
1413:0731-3810
1299:1176-2551
1086:0066-4170
1072:: 77–96.
973:(erratum)
968:Q52880664
942:0091-6765
804:and beta-
752:pyrethrum
741:mammalian
737:pyrethrum
693:mutations
630:Wisconsin
488:food webs
400:pyrethrin
291:Allethrin
171:inhibitor
139:membranes
111:food webs
36:Allethrin
3377:Spinosad
3279:Paraoxon
3274:Malaoxon
3246:Xanthone
3221:Spinosad
3177:Limonene
3157:Fipronil
3086:Ryanodol
3058:Ryanoids
2872:Tribufos
2862:Terbufos
2847:Schradan
2737:Fenthion
2722:Ethoprop
2677:Diazinon
2627:Acephate
2564:Dieldrin
2499:Beta-HCH
2345:Cryolite
2302:Propoxur
2282:Methomyl
2247:Carbaryl
2227:Aldicarb
2148:22504519
2060:24704279
2028:: 1–17.
1873:27422270
1865:19058634
1824:Archived
1799:19580578
1756:19336711
1708:CBC News
1609:29492806
1531:19897392
1522:10911430
1472:29389244
1429:22213256
1421:10778904
1376:29928068
1315:32523158
1307:16180929
1259:20121184
1214:21246035
1173:PLOS ONE
1153:31777441
1102:31881940
1009:11812616
964:Wikidata
960:29648420
744:toxicity
588:reptiles
504:sunlight
480:gadflies
476:mayflies
284:Examples
226:with an
103:gadflies
99:mayflies
3215:Sesamex
3107:Amitraz
2852:Temefos
2842:R-16661
2822:Phosmet
2812:Phorate
2772:Mipafox
2697:Dimefox
2589:Lindane
2559:Dicofol
2534:1,2-DCE
2529:1,1-DCE
2524:1,4-DCB
2519:1,2-DCB
2072:NIHMSID
2068:6332754
2051:4484874
1992:(UCANR)
1917:3496140
1617:3604324
1367:6005695
1239:Bibcode
1205:3016336
1182:Bibcode
1144:6861428
1094:2539040
951:6071803
719:History
715:genes.
695:confer
610:bedbugs
576:mammals
424:Scourge
305:Capture
301:Talstar
270:silicon
228:alcohol
145:with a
50:isomers
38:isomers
3127:Cartap
2827:Phoxim
2717:Ethion
2584:Kepone
2574:Endrin
2494:Aldrin
2292:Oxamyl
2146:
2066:
2058:
2048:
2040:
1915:
1907:
1871:
1863:
1805:
1797:
1754:
1671:
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1092:
1084:
1007:
966:
958:
948:
940:
881:9 June
874:. The
846:
564:ataxia
522:Humans
517:Safety
322:Baygon
311:, and
58:is an
2782:Naled
2599:Mirex
2120:(PDF)
2064:S2CID
1913:JSTOR
1869:S2CID
1803:S2CID
1685:ORCID
1683:. MG
1669:S2CID
1647:(5).
1613:S2CID
1535:S2CID
1425:S2CID
1311:S2CID
1098:S2CID
1068:(1).
654:Sudan
580:birds
410:Anvil
262:ether
131:axons
3284:TCPy
3269:Oxon
2554:DFDT
2144:PMID
2056:PMID
2038:ISSN
1905:ISSN
1861:PMID
1795:PMID
1752:PMID
1735:JAMA
1715:2016
1661:ISSN
1605:PMID
1566:ISBN
1527:PMID
1509:ISSN
1468:PMID
1417:PMID
1409:ISSN
1372:PMID
1352:ISBN
1303:PMID
1295:ISSN
1255:PMID
1210:PMID
1149:PMID
1090:PMID
1082:ISSN
1005:PMID
956:PMID
938:ISSN
883:2012
844:ISBN
788:and
757:The
731:and
628:and
616:and
590:and
584:fish
560:dogs
556:cats
540:coma
468:bees
91:bees
76:and
2549:DDT
2544:DDE
2539:DDD
2134:doi
2098:doi
2046:PMC
2030:doi
1897:doi
1853:doi
1785:doi
1744:doi
1740:301
1653:doi
1597:doi
1558:doi
1517:PMC
1501:doi
1458:doi
1401:doi
1362:PMC
1344:doi
1287:doi
1247:doi
1200:PMC
1190:doi
1139:PMC
1131:doi
1074:doi
1038:doi
997:doi
993:171
946:PMC
930:doi
926:126
836:doi
748:DDT
709:kdr
701:DDT
699:to
690:kdr
686:kdr
666:in
652:in
642:in
614:DDT
578:or
502:by
173:of
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