814:
systems. If results indicate a relationship, the chemical progresses to Tier 2 testing. The purpose of Tier 2 is to determine whether a substance that interacts with the EAT hormone system exerts an adverse effect in humans or wildlife, and to develop a dose-response that, in association with exposure data, can be used to assess risk. PBO is one of the chemicals selected by EPA to be part of the initial effort under the EDSP. The EPA issued its first list of chemicals for EDSP testing in 2009, consisting of over 60 pesticide chemicals, including the insecticide synergist PBO. The first list of chemicals for EDSP screening is not based on a potential for endocrine activity or a potential for adverse effects. Rather, the list is based on an EPA prioritization regarding exposure potential. PBO was added to this list because of its wide use pattern (1500 products registered with US EPA), and people may be exposed to low levels of PBO in their diets, from treated surfaces in their homes (e.g., carpet), and in certain occupations (e.g., pest control operators).
611:(FIFRA), the law that gives United States EPA its authority to regulate pesticides, includes certain synergists in its definition of a “pesticide” and is thus subject to the same approval and registration as products that kill pests, like the insecticides with which PBO is formulated. Pesticide registration is the process through which United States EPA examines the ingredients of a pesticide, where and how the pesticide is used (e.g., whole room fogger, crack-and-crevice, etc.), and the specific use pattern (amount and frequency of its use). United States EPA also evaluates the pesticide to ensure that it will not have unreasonable adverse effects on humans, the environment and non-target species. The United States EPA must register pesticides before they may be sold or distributed in the United States. Registration is required for the pesticide itself, as well as for all products containing it. The World Health Organization recognizes the public health value of PBO when used in conjunction with the synthetic pyrethroids
972:
Most of the studies were conducted with formulations of pyrethrins/PBO and synthetic pyrethroids/PBO, and focused on the indoor use of fogger and aerosol products. Carpet and vinyl flooring surfaces were selected because of their different physical and chemical properties, and because they represent a significant percentage of the floor coverings used in homes in North
America. While the focus of the NDETF effort was on total-release foggers, a study was also conducted to determine both dispersion (air levels) and deposition (on flooring) of pyrethrins/PBO resulting from the use of a hand held aerosol spray can. Potential direct exposure of the user was also measured. Air sampling from the breathing zone of the applicator and analysis of residues on cotton gloves was performed. This data was submitted to the United States EPA and was key to the agency’s comprehensive risk assessment for PBO.
825:
guidelines. The WoE analysis for PBO examines each EDSP Tier 1 assay conducted for PBO. It discusses the purpose of the assay, and summarizes the study design and results and provides an overall conclusion for each assay. All 11 individual assays are then considered together to arrive at an overall conclusion for the outcome of the Tier 1 battery. For some assays, other scientifically relevant information is also considered as part of the assessment. The purpose of the WoE analysis is to determine whether PBO has the potential to interact with the endocrine system, as determined by EDSP Tier 1 assays, the Tier 1 battery as a whole and OSRI. A determination that a chemical has the potential to interact with the endocrine system would trigger a need for EDSP Tier 2 testing. The EPA is planning to issue their WOE assessment in late 2014 or early 2015.
24:
277:
164:
33:
557:). A wide variety of water-based PBO-containing products such as crack and crevice sprays, total release foggers, and flying insect sprays are produced for and sold to consumers for home use. PBO has an important public health role as a synergist used in pyrethrins and pyrethroid formulations used for mosquito control (e.g. space sprays, surface sprays and bed nets). Because of its limited, if any, insecticidal properties, PBO is never used alone.
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529:. Pyrethrum is a type of potent insecticide that kills mosquitoes and other disease-carrying vectors, thereby providing public health benefits, such as preventing malaria. Although exhibiting little intrinsic insecticidal activity of its own, PBO increases the effectiveness of pyrethrins, thus it is called a synergist. PBO was first patented in 1947 in the US by Herman Wachs.
821:. This includes the recently developed data to assess the possible interaction of PBO with the endocrine system. The Piperonyl Butoxide Task Force II, a group of companies that produces or markets PBO-containing products, has conducted all 11 EDSP Tier 1 screens and has submitted all required documentation and study reports.
541:
most commonly registered synergists as measured by the number of formulas in which it is present. It is approved for pre- and postharvest application to a wide variety of crops and commodities, including grain, fruits and vegetables. The application rates are low; the highest single rate is 0.5 lbs PBO/acre.
628:
United States EPA Good
Laboratory Practices (GLPs), a system of processes and controls to ensure the consistency, integrity, quality, and reproducibility of laboratory studies conducted in support of pesticides registration. The following types of studies have been conducted in support of PBO registration:
813:
screening program (EDSP) designed to examine potential effects of substances on the estrogenic, androgenic, and thyroid (EAT) hormone systems in both humans and wildlife. Tier 1 consists of 11 assays, and is designed to determine whether a substance has the potential to interact with the EAT hormone
540:
PBO was first registered in the United States in the 1950s. PBO is mainly used in combination with insecticides, such as natural pyrethrins or synthetic pyrethroids, in ratios (PBO: pyrethrins) ranging from 3:1 to 20:1. Appearing in over 1,500 United States EPA-registered products, PBO is one of the
824:
The US EPA intends to use a weight of evidence (WoE) approach for assessing EDSP Tier 1 results. While the agency issued WOE guidelines, no actual WOE assessments have yet been conducted and released to the registrants. The PBTFII has conducted a WoE analysis for PBO that is consistent with EPA’s
627:
Numerous toxicology studies have been conducted over the past 40 years on PBO examining the full range of potential toxic effects. These studies were conducted in accord with regulatory requirements put forth by the United States EPA or other international agencies. Many were conducted following
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Given the extensive non-dietary use of PBO, manufacturers of PBO and marketers of PBO-containing products formed the Non-Dietary
Exposure Task Force (NDETF) in 1996 to develop a long-term research program to more fully understand the phenomenon of human exposure to insecticides used in the home.
860:
The EPA classifies PBO as a group C carcinogen – "possibly carcinogenic to humans." Under the auspices of the United
Nations, the Food and Agriculture Organization/World Health Organization (FAO/WHO) Joint Meeting on Pesticide Residues evaluated the entire body of toxicology of PBO several times
702:
Acute toxicity studies are designed to identify potential hazards from acute exposures. The studies usually employ a single or a few high doses over a short time period. The data are used for the development of appropriate precautionary statements for pesticide product labels. Acute studies
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system. The MFO system is the primary route of detoxification in insects, and causes the oxidative breakdown of insecticides such as pyrethrins and the synthetic pyrethroids – thus when PBO is added, higher insecticide levels remain in the insect to exercise their lethal effect. An important
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PBO caused an increase in liver tumors in mice that ingested high levels of PBO in the diet for their entire lifetimes. The scientific identification and analysis of the key events leading to the formation of the mouse liver tumors suggest that the events are not likely to occur in humans.
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NOAELs were derived for PBO from both subchronic and chronic studies. These NOAELs are used by the EPA to conduct risk assessments for all individual uses of PBO to ensure that all registered products with PBO pose a reasonable certainty of no harm used according to the label directions.
1327:
Dhopeshwarkar, Amey S.; Jain, Saurabh; Liao, Chengyong; Ghose, Sudip K.; Bisset, Kathleen M.; Nicholson, Russell A. (2011-03-01). "The actions of benzophenanthridine alkaloids, piperonyl butoxide and (S)-methoprene at the G-protein coupled cannabinoid CB₁ receptor in vitro".
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since 1965. They concluded that, at doses up to internationally accepted standards for a maximum tolerated dose, PBO is not considered to be carcinogenic in the mouse or rat, thus leading to the conclusion that PBO is not carcinogenic to humans.
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Subchronic and chronic studies examine the toxicity of longer-term, repeated exposure to chemicals. They may range from 90 days for subchronic studies, to 12–24 months for full lifetime chronic studies, designed to determine potential for
1522:
Everson, Joshua L.; Sun, Miranda R.; Fink, Dustin M.; Heyne, Galen W.; Melberg, Cal G.; Nelson, Kia F.; Doroodchi, Padydeh; Colopy, Lydia J.; Ulschmid, Caden M.; Martin, Alexander A.; McLaughlin, Matthew T.; Lipinski, Robert J. (2019).
734:
The available data indicate that less than 3% of the amount on the skin (forearm) is absorbed over an 8-hour period. Other studies with a pediculicide formulation indicate that about 2% crossed the skin and about 8% crossed the scalp.
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It is used extensively as an ingredient with insecticides to control insect pests in and around the home, in food-handling establishments such as restaurants, and for human and veterinary applications against ectoparasites
1291:
Conney, Allan H.; Chang, Richard; Levin, Wayne M.; Garbut, Arnold; Munro-Faure, A. Douglas; Peck, Anthony W.; Beckenham, Alan Bye (February 1972). "Effects of
Piperonyl Butoxide on Drug Metabolism in Rodents and Man".
896:
PBO is moderately to highly toxic to aquatic invertebrates, such as water fleas and shrimp. At lower, long-term doses, water flea reproduction was affected. PBO is highly toxic to amphibians in the tadpole stage.
881:. Even doses of PBO that did not cause overt holoprosencephaly associated facial abnormalities were found to cause subtle neuroanatomical defects, for which the cognitive or behavioral consequences are unknown.
996:
National
Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North
1242:
Moores, G. D., Philippou, D., Borzatta, V., Trincia, P., Jewess, P., Gunning, R., Bingham, G. (2009). "An analogue of piperonyl butoxide facilitates the characterisation of metabolic resistance".
809:
The Food
Quality Protection Act (FQPA) of 1996 required the United States EPA to address the issue of endocrine disruption. Since the passage of the FQPA, the US EPA has developed a two-tiered
838:. They are also intended to identify any noncancer effects, as well as a clear no observable adverse effect level (NOAEL) that is used for risk assessment. Studies conducted on PBO include:
1525:"Developmental Toxicity Assessment of Piperonyl Butoxide Exposure Targeting Sonic Hedgehog Signaling and Forebrain and Face Morphogenesis in the Mouse: An in Vitro and in Vivo Study"
980:
The US EPA, in their re-registration eligibility decision, determined "no risks of concern" existed for householders mixing, loading, handling, or applying PBO-containing products.
510:
877:(SMO). PBO was found to be capable of causing dose-dependent brain and face malformations in mice exposed during early development, including the rare human birth defect
1180:
Devine, G.J.; Denholm, I. (December 1998). "An unconventional use of piperonyl butoxide for managing the cotton whitefly, Bemisia tabaci (Hemiptera: Aleyrodidae)".
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PBO has a low acute toxicity by oral, inhalation, and dermal routes in adults. It is minimally irritating to the eyes and skin. It is a not a skin sensitizer.
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608:
451:
1277:
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PBO is regulated in the United States and some other countries as a pesticide, even though PBO does not have this property. The United States
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2614:
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PBO does not appear to have a significant effect on the MFO system in humans. PBO is found to be an efficacious, low-potency, neutral
574:
consequence of this property is that, by enhancing the activity of a given insecticide, less may be used to achieve the same result.
532:
There are 3 known manufacturer of PBO in the world, Endura, Tagros and
Catasynth (Anthea) who manufacture PBO through the MDB route.
565:
PBO acts as an insecticide synergist by inhibiting the natural defense mechanisms of the insect, the most important of which is the
888:
study found that PBO exposure was correlated with dose-dependent reductions in neurocognitive development in 3-year old children.
1665:
493:. That is, despite having no pesticidal activity of its own, it enhances the potency of certain pesticides such as carbamates,
446:
101:
1241:
1089:
Glynne-Jones, D. (1998). History of PBO In "PBO—The
Insecticide Synergist" (D. Glynne Jones, ed.). Academic Press, San Diego.
1071:
1038:
932:
770:
663:
1426:
Wester, RC; Bucks, DA; Maibach, HI (1994). "Human in vivo percutaneous absorption of pyrethrin and piperonyl butoxide".
1470:
Wang, J.; Lu, J.; Mook Jr, R. A.; Zhang, M.; Zhao, S.; Barak, L. S.; Freedman, J. H.; Lyerly, H. K.; Chen, W. (2012).
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796:
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PBO was developed in the late 1930s and early 1940s to enhance the performance of the naturally derived insecticide
23:
2011:
458:
300:
InChI=1S/C19H30O5/c1-3-5-7-20-8-9-21-10-11-22-14-17-13-19-18(23-15-24-19)12-16(17)6-4-2/h12-13H,3-11,14-15H2,1-2H3
310:
InChI=1/C19H30O5/c1-3-5-7-20-8-9-21-10-11-22-14-17-13-19-18(23-15-24-19)12-16(17)6-4-2/h12-13H,3-11,14-15H2,1-2H3
1207:
Casida, John E. (May 1970). "Mixed-function oxidase involvement in the biochemistry of insecticide synergists".
2006:
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1966:
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873:, a critical regulator of brain and face development in all vertebrates, via antagonism of the protein
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1981:
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Children, National
Research Council (US) Committee on Pesticides in the Diets of Infants and (1993),
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171:
1472:"The Insecticide Synergist Piperonyl Butoxide Inhibits Hedgehog Signaling: Assessing Chemical Risks"
1148:"Pyrethrum Extract And Piperonyl Butoxide (Topical Route) Description and Brand Names - Mayo Clinic"
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652:
272:
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1842:
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JMPR (1995) PBO A monograph prepared by the Joint FAO/WHO Meeting on Pesticide Residues, Geneva.)
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763:
656:
2885:
2880:
2810:
2770:
1822:
1574:"Impact of prenatal exposure to piperonyl butoxide and permethrin on 36-month neurodevelopment"
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2870:
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1271:
1572:
Horton, M. K.; Rundle, A.; Camann, D. E.; Boyd Barr, D.; Rauh, V. A.; Whyatt, R. M. (2011).
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US Environmental Protection Agency. Reregistration Eligibility Decision for PBO, June, 2006.
1971:
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US Environmental Protection Agency. Reregistration Eligibility Decision for PBO, June, 2006
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and the chloromethyl derivative of hydrogenated safrole (dihydrosafrole); or through
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Federal Insecticide, Fungicide, and Rodenticide Act7 U.S.C. §136 et seq. (1996)
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National Pesticide Information Center – Piperonyl Butoxide General Fact Sheet
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Osimitz, Thomas G. (2010). "The Safety Assessment of Piperonyl Butoxide".
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1124:"Pyrethrin and Piperonyl Butoxide Topical: MedlinePlus Drug Information"
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No evidence suggests that PBO disrupts the normal functioning of the
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Except where otherwise noted, data are given for materials in their
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and "Sulfoxide" (not to be confused with the functional group).
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and is produced from the condensation of the sodium salt of
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2016:
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24-month chronic toxicity/carcinogenicity study in rats
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18-month chronic toxicity/carcinogenicity study in mice
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609:
Federal Insecticide, Fungicide, and Rodenticide Act
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407:180 °C (356 °F; 453 K) at 1 mmHg
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1398:Pesticides in the Diets of Infants and Children
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1023:Ullmann's Encyclopedia of Industrial Chemistry
829:Subchronic and chronic/carcinogenicity studies
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1622:"Piperonyl Butoxide (PBO) General Fact Sheet"
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1021:Metcalf, Robert L. (2000). "Insect Control".
1276:: CS1 maint: multiple names: authors list (
939:. Unsourced material may be challenged and
777:. Unsourced material may be challenged and
670:. Unsourced material may be challenged and
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1209:Journal of Agricultural and Food Chemistry
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959:Learn how and when to remove this message
797:Learn how and when to remove this message
690:Learn how and when to remove this message
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477:) is a pale yellow to light brown liquid
242:
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505:. It is a semisynthetic derivative of
1056:Hayes' Handbook of Pesticide Toxicology
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1020:
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900:
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422:170 °C (338 °F; 443 K)
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1626:National Pesticide Information Center
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1083:
303:Key: FIPWRIJSWJWJAI-UHFFFAOYSA-N
120:
990:
937:adding citations to reliable sources
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775:adding citations to reliable sources
742:
729:
668:adding citations to reliable sources
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622:
397:21 °C (70 °F; 294 K)
313:Key: FIPWRIJSWJWJAI-UHFFFAOYAD
213:
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13:
1182:Bulletin of Entomological Research
1080:
1064:10.1016/B978-0-12-374367-1.00099-9
975:
869:PBO has been found to inhibit the
842:90-day inhalation toxicology study
14:
2897:
1529:Environmental Health Perspectives
891:
569:system, (MFOs) also known as the
334:CCCCOCCOCCOCC1=CC2=C(C=C1CCC)OCO2
1330:European Journal of Pharmacology
1294:Archives of Environmental Health
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1628:. Oregon State University. 2017
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1400:, National Academies Press (US)
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1320:
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432:(at 25 °C , 100 kPa).
1394:"Methods for Toxicity Testing"
1306:10.1080/00039896.1972.10666058
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1000:
865:Developmental toxicity studies
1:
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602:
1440:10.1016/0278-6915(84)90036-x
1428:Food and Chemical Toxicology
1342:10.1016/j.ejphar.2010.11.033
7:
2160:Diisopropyl fluorophosphate
377:338.438 g/mol
10:
2902:
871:Hedgehog signaling pathway
520:
511:2-(2-butoxyethoxy) ethanol
2839:Purpureocillium lilacinum
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2727:
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2085:
1952:
1889:
1841:
1798:Chromated copper arsenate
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1730:m-Cumenyl methylcarbamate
1685:
1194:10.1017/S0007485300054262
515:1,2-Methylenedioxybenzene
426:
411:
342:
322:
287:
60:
44:
39:
30:
21:
1843:Insect growth regulators
1031:10.1002/14356007.a14_263
2832:Paenibacillus popilliae
1482:(2). Tox Sci: 517–523.
619:used in mosquito nets.
535:
2811:Metarhizium anisopliae
2790:Beauveria brongniartii
2771:Bacillus thuringiensis
1823:Lead hydrogen arsenate
1590:10.1542/peds.2010-0133
1476:Toxicological Sciences
1058:. pp. 2127–2151.
632:Acute toxicity studies
567:mixed-function oxidase
2825:Lecanicillium lecanii
1488:10.1093/toxsci/kfs165
595:insecticides include
591:Other synergists for
50:5-{methyl}-6-propyl-2
1972:Carbon tetrachloride
933:improve this section
771:improve this section
739:Endocrine disruption
664:improve this section
46:Preferred IUPAC name
2866:Household chemicals
2804:Metarhizium acridum
2534:Chlorantraniliprole
2130:Chlorpyrifos-methyl
1803:Copper(II) arsenate
1788:Aluminium phosphide
1780:Inorganic compounds
1535:(10). EHP: 107006.
1221:10.1021/jf60171a013
901:Exposure assessment
811:endocrine disruptor
713:Inhalation toxicity
561:Mechanism of action
18:
17:Piperonyl butoxide
2797:Isaria fumosorosea
2783:Beauveria bassiana
2679:Piperonyl butoxide
2480:chrysanthemic acid
1818:Diatomaceous earth
1152:www.mayoclinic.org
722:Skin sensitization
471:Piperonyl butoxide
459:Infobox references
16:
2853:
2852:
2654:+milbemycin oxime
2335:Tetrachlorvinphos
2300:Pirimiphos-methyl
2260:Oxydemeton-methyl
1808:Copper(I) cyanide
1073:978-0-12-374367-1
1040:978-3-527-30385-4
969:
968:
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879:holoprosencephaly
807:
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730:Dermal absorption
700:
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692:
623:Hazard assessment
583:G-protein-coupled
489:formulations for
467:Chemical compound
465:
464:
256:CompTox Dashboard
102:Interactive image
54:-1,3-benzodioxole
2893:
2539:Cyantraniliprole
2270:Parathion-methyl
2140:Demeton-S-methyl
2087:Organophosphorus
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1288:
1282:
1281:
1275:
1267:
1239:
1233:
1232:
1204:
1198:
1197:
1177:
1171:
1168:
1162:
1161:
1159:
1158:
1144:
1138:
1137:
1135:
1134:
1120:
1114:
1113:
1111:
1110:
1096:
1090:
1087:
1078:
1077:
1051:
1045:
1044:
1018:
1009:
1004:
998:
994:
964:
957:
953:
950:
944:
913:
905:
819:endocrine system
802:
795:
791:
788:
782:
751:
743:
695:
688:
684:
681:
675:
644:
636:
571:cytochrome P-450
479:organic compound
449:
443:
440:
439:
350:Chemical formula
280:
279:
264:
262:
246:
226:
215:
201:
174:
166:
155:
144:
124:
104:
80:
35:
26:
19:
15:
2901:
2900:
2896:
2895:
2894:
2892:
2891:
2890:
2856:
2855:
2854:
2849:
2818:Nomuraea rileyi
2756:
2723:
2563:Other chemicals
2558:
2520:
2349:
2120:Chlorfenvinphos
2105:Azinphos-methyl
2081:
1954:Organochlorides
1948:
1885:
1837:
1833:Scheele's Green
1774:
1681:
1672:
1642:
1641:
1631:
1629:
1620:
1619:
1615:
1584:(3): e699-706.
1570:
1566:
1541:10.1289/EHP5260
1520:
1513:
1468:
1464:
1459:
1455:
1424:
1420:
1415:
1411:
1403:
1401:
1390:
1386:
1381:
1374:
1369:
1365:
1325:
1321:
1289:
1285:
1269:
1268:
1256:10.1002/ps.1661
1244:Pest Manag. Sci
1240:
1236:
1205:
1201:
1178:
1174:
1169:
1165:
1156:
1154:
1146:
1145:
1141:
1132:
1130:
1128:medlineplus.gov
1122:
1121:
1117:
1108:
1106:
1098:
1097:
1093:
1088:
1081:
1074:
1052:
1048:
1041:
1019:
1012:
1005:
1001:
995:
991:
986:
978:
976:Risk assessment
965:
954:
948:
945:
930:
914:
903:
894:
867:
831:
803:
792:
786:
783:
768:
752:
741:
732:
719:Skin irritation
707:Dermal toxicity
696:
685:
679:
676:
661:
645:
634:
625:
605:
563:
538:
523:
468:
461:
456:
455:
454: ?)
445:
441:
437:
433:
366:
362:
358:
352:
338:
335:
330:
329:
318:
315:
314:
311:
305:
304:
301:
295:
294:
283:
265:
258:
249:
229:
216:
204:
184:
147:
127:
107:
94:
83:
70:
56:
55:
12:
11:
5:
2899:
2889:
2888:
2883:
2878:
2873:
2868:
2851:
2850:
2848:
2847:
2842:
2835:
2828:
2821:
2814:
2807:
2800:
2793:
2786:
2779:
2774:
2766:
2764:
2758:
2757:
2755:
2754:
2749:
2744:
2739:
2733:
2731:
2725:
2724:
2722:
2721:
2716:
2711:
2706:
2701:
2696:
2691:
2686:
2672:
2667:
2662:
2657:
2647:
2642:
2637:
2635:Hydramethylnon
2632:
2627:
2622:
2617:
2612:
2607:
2602:
2597:
2592:
2587:
2582:
2577:
2572:
2566:
2564:
2560:
2559:
2557:
2556:
2551:
2546:
2541:
2536:
2530:
2528:
2522:
2521:
2519:
2518:
2513:
2508:
2503:
2498:
2493:
2488:
2483:
2465:
2460:
2455:
2450:
2445:
2440:
2435:
2430:
2425:
2420:
2415:
2410:
2405:
2400:
2395:
2390:
2385:
2380:
2375:
2370:
2365:
2359:
2357:
2351:
2350:
2348:
2347:
2342:
2337:
2332:
2327:
2322:
2317:
2312:
2307:
2302:
2297:
2292:
2287:
2282:
2277:
2272:
2267:
2262:
2257:
2252:
2247:
2242:
2237:
2232:
2227:
2222:
2217:
2212:
2207:
2202:
2197:
2192:
2187:
2182:
2177:
2172:
2167:
2162:
2157:
2152:
2147:
2142:
2137:
2132:
2127:
2122:
2117:
2115:Chlorethoxyfos
2112:
2107:
2102:
2097:
2091:
2089:
2083:
2082:
2080:
2079:
2074:
2069:
2064:
2059:
2054:
2049:
2044:
2039:
2034:
2029:
2024:
2019:
2014:
2009:
2004:
1999:
1994:
1989:
1984:
1979:
1974:
1969:
1964:
1958:
1956:
1950:
1949:
1947:
1946:
1941:
1936:
1931:
1926:
1921:
1916:
1911:
1906:
1901:
1895:
1893:
1891:Neonicotinoids
1887:
1886:
1884:
1883:
1878:
1873:
1868:
1863:
1858:
1853:
1847:
1845:
1839:
1838:
1836:
1835:
1830:
1825:
1820:
1815:
1810:
1805:
1800:
1795:
1790:
1784:
1782:
1776:
1775:
1773:
1772:
1767:
1762:
1757:
1752:
1747:
1742:
1737:
1732:
1727:
1722:
1717:
1712:
1707:
1702:
1697:
1691:
1689:
1683:
1682:
1671:
1670:
1663:
1656:
1648:
1640:
1639:
1613:
1564:
1511:
1462:
1453:
1418:
1409:
1384:
1372:
1363:
1319:
1283:
1250:(2): 150–154.
1234:
1215:(5): 753–772.
1199:
1188:(6): 601–610.
1172:
1163:
1139:
1115:
1091:
1079:
1072:
1046:
1039:
1010:
999:
988:
987:
985:
982:
977:
974:
967:
966:
917:
915:
908:
902:
899:
893:
892:Animal impacts
890:
866:
863:
850:
849:
846:
843:
836:carcinogenesis
830:
827:
805:
804:
755:
753:
746:
740:
737:
731:
728:
724:
723:
720:
717:
714:
711:
710:Eye irritation
708:
698:
697:
648:
646:
639:
633:
630:
624:
621:
604:
601:
562:
559:
537:
534:
522:
519:
466:
463:
462:
457:
435:
434:
430:standard state
427:
424:
423:
420:
414:
413:
409:
408:
405:
399:
398:
395:
389:
388:
385:
379:
378:
375:
369:
368:
364:
360:
356:
353:
348:
345:
344:
340:
339:
337:
336:
333:
325:
324:
323:
320:
319:
317:
316:
312:
309:
308:
306:
302:
299:
298:
290:
289:
288:
285:
284:
282:
281:
268:
266:
254:
251:
250:
248:
247:
239:
237:
231:
230:
228:
227:
219:
217:
209:
206:
205:
203:
202:
194:
192:
186:
185:
183:
182:
178:
176:
168:
167:
157:
149:
148:
146:
145:
137:
135:
129:
128:
126:
125:
117:
115:
109:
108:
106:
105:
97:
95:
88:
85:
84:
82:
81:
73:
71:
66:
63:
62:
58:
57:
49:
48:
42:
41:
37:
36:
28:
27:
9:
6:
4:
3:
2:
2898:
2887:
2886:Glycol ethers
2884:
2882:
2881:Benzodioxoles
2879:
2877:
2874:
2872:
2869:
2867:
2864:
2863:
2861:
2846:
2843:
2841:
2840:
2836:
2834:
2833:
2829:
2827:
2826:
2822:
2820:
2819:
2815:
2813:
2812:
2808:
2806:
2805:
2801:
2799:
2798:
2794:
2792:
2791:
2787:
2785:
2784:
2780:
2778:
2775:
2773:
2772:
2768:
2767:
2765:
2763:
2762:Biopesticides
2759:
2753:
2750:
2748:
2745:
2743:
2740:
2738:
2735:
2734:
2732:
2730:
2726:
2720:
2719:Metaflumizone
2717:
2715:
2712:
2710:
2707:
2705:
2702:
2700:
2697:
2695:
2692:
2690:
2687:
2684:
2680:
2676:
2673:
2671:
2668:
2666:
2663:
2661:
2658:
2655:
2651:
2648:
2646:
2643:
2641:
2638:
2636:
2633:
2631:
2628:
2626:
2623:
2621:
2618:
2616:
2613:
2611:
2608:
2606:
2603:
2601:
2600:Chlordimeform
2598:
2596:
2593:
2591:
2588:
2586:
2583:
2581:
2578:
2576:
2573:
2571:
2568:
2567:
2565:
2561:
2555:
2552:
2550:
2547:
2545:
2544:Flubendiamide
2542:
2540:
2537:
2535:
2532:
2531:
2529:
2527:
2523:
2517:
2516:Transfluthrin
2514:
2512:
2509:
2507:
2504:
2502:
2499:
2497:
2494:
2492:
2489:
2487:
2484:
2481:
2477:
2473:
2469:
2466:
2464:
2461:
2459:
2456:
2454:
2451:
2449:
2446:
2444:
2441:
2439:
2436:
2434:
2431:
2429:
2426:
2424:
2423:Fenpropathrin
2421:
2419:
2416:
2414:
2413:Esfenvalerate
2411:
2409:
2406:
2404:
2401:
2399:
2396:
2394:
2391:
2389:
2386:
2384:
2381:
2379:
2376:
2374:
2371:
2369:
2366:
2364:
2361:
2360:
2358:
2356:
2352:
2346:
2343:
2341:
2338:
2336:
2333:
2331:
2328:
2326:
2323:
2321:
2318:
2316:
2313:
2311:
2308:
2306:
2303:
2301:
2298:
2296:
2293:
2291:
2288:
2286:
2283:
2281:
2278:
2276:
2273:
2271:
2268:
2266:
2263:
2261:
2258:
2256:
2253:
2251:
2248:
2246:
2245:Monocrotophos
2243:
2241:
2238:
2236:
2233:
2231:
2228:
2226:
2225:Methamidophos
2223:
2221:
2218:
2216:
2213:
2211:
2208:
2206:
2203:
2201:
2198:
2196:
2193:
2191:
2188:
2186:
2183:
2181:
2178:
2176:
2173:
2171:
2168:
2166:
2163:
2161:
2158:
2156:
2153:
2151:
2148:
2146:
2143:
2141:
2138:
2136:
2133:
2131:
2128:
2126:
2123:
2121:
2118:
2116:
2113:
2111:
2108:
2106:
2103:
2101:
2098:
2096:
2093:
2092:
2090:
2088:
2084:
2078:
2075:
2073:
2070:
2068:
2065:
2063:
2060:
2058:
2055:
2053:
2050:
2048:
2045:
2043:
2040:
2038:
2035:
2033:
2030:
2028:
2025:
2023:
2020:
2018:
2015:
2013:
2010:
2008:
2005:
2003:
2000:
1998:
1995:
1993:
1990:
1988:
1985:
1983:
1980:
1978:
1975:
1973:
1970:
1968:
1965:
1963:
1960:
1959:
1957:
1955:
1951:
1945:
1942:
1940:
1937:
1935:
1932:
1930:
1927:
1925:
1922:
1920:
1917:
1915:
1912:
1910:
1907:
1905:
1902:
1900:
1897:
1896:
1894:
1892:
1888:
1882:
1879:
1877:
1874:
1872:
1869:
1867:
1864:
1862:
1859:
1857:
1856:Diflubenzuron
1854:
1852:
1849:
1848:
1846:
1844:
1840:
1834:
1831:
1829:
1826:
1824:
1821:
1819:
1816:
1814:
1811:
1809:
1806:
1804:
1801:
1799:
1796:
1794:
1791:
1789:
1786:
1785:
1783:
1781:
1777:
1771:
1768:
1766:
1763:
1761:
1758:
1756:
1753:
1751:
1748:
1746:
1743:
1741:
1738:
1736:
1733:
1731:
1728:
1726:
1723:
1721:
1718:
1716:
1713:
1711:
1708:
1706:
1703:
1701:
1698:
1696:
1693:
1692:
1690:
1688:
1684:
1680:
1676:
1669:
1664:
1662:
1657:
1655:
1650:
1649:
1646:
1627:
1623:
1617:
1609:
1605:
1600:
1595:
1591:
1587:
1583:
1579:
1575:
1568:
1560:
1556:
1551:
1546:
1542:
1538:
1534:
1530:
1526:
1518:
1516:
1507:
1503:
1498:
1493:
1489:
1485:
1481:
1477:
1473:
1466:
1457:
1449:
1445:
1441:
1437:
1433:
1429:
1422:
1416:(Selim, 1995)
1413:
1399:
1395:
1388:
1379:
1377:
1367:
1359:
1355:
1351:
1347:
1343:
1339:
1335:
1331:
1323:
1315:
1311:
1307:
1303:
1300:(2): 97–106.
1299:
1295:
1287:
1279:
1273:
1265:
1261:
1257:
1253:
1249:
1245:
1238:
1230:
1226:
1222:
1218:
1214:
1210:
1203:
1195:
1191:
1187:
1183:
1176:
1167:
1153:
1149:
1143:
1129:
1125:
1119:
1105:
1101:
1095:
1086:
1084:
1075:
1069:
1065:
1061:
1057:
1050:
1042:
1036:
1032:
1028:
1024:
1017:
1015:
1008:
1003:
993:
989:
981:
973:
963:
960:
952:
949:December 2016
942:
938:
934:
928:
927:
923:
918:This section
916:
912:
907:
906:
898:
889:
887:
882:
880:
876:
872:
862:
858:
854:
847:
844:
841:
840:
839:
837:
826:
822:
820:
815:
812:
801:
798:
790:
787:December 2016
780:
776:
772:
766:
765:
761:
756:This section
754:
750:
745:
744:
736:
727:
721:
718:
716:Oral toxicity
715:
712:
709:
706:
705:
704:
694:
691:
683:
680:December 2016
673:
669:
665:
659:
658:
654:
649:This section
647:
643:
638:
637:
629:
620:
618:
614:
610:
600:
598:
594:
589:
587:
586:CB1 receptors
584:
580:
575:
572:
568:
558:
556:
552:
548:
542:
533:
530:
528:
518:
516:
512:
508:
504:
500:
496:
492:
488:
485:component of
484:
480:
476:
472:
460:
453:
448:
431:
425:
421:
419:
416:
415:
410:
406:
404:
403:Boiling point
401:
400:
396:
394:
393:Melting point
391:
390:
386:
384:
381:
380:
376:
374:
371:
370:
354:
351:
347:
346:
341:
332:
331:
328:
321:
307:
297:
296:
293:
286:
278:
274:
273:DTXSID1021166
270:
269:
267:
257:
253:
252:
245:
241:
240:
238:
236:
233:
232:
225:
221:
220:
218:
212:
208:
207:
200:
196:
195:
193:
191:
188:
187:
180:
179:
177:
175:
170:
169:
165:
161:
158:
156:
154:ECHA InfoCard
151:
150:
143:
139:
138:
136:
134:
131:
130:
123:
122:ChEMBL1201131
119:
118:
116:
114:
111:
110:
103:
99:
98:
96:
92:
87:
86:
79:
75:
74:
72:
69:
65:
64:
59:
53:
47:
43:
38:
34:
29:
25:
20:
2871:Insecticides
2837:
2830:
2823:
2816:
2809:
2802:
2795:
2788:
2781:
2769:
2704:Tebufenpyrad
2699:Tebufenozide
2678:
2605:Chlorfenapyr
2580:Azadirachtin
2511:Tralomethrin
2506:Tetramethrin
2448:Metofluthrin
2403:Deltamethrin
2398:Cyphenothrin
2393:Cypermethrin
2378:Bioallethrin
2325:Tebupirimfos
2230:Methidathion
2200:Fenitrothion
2125:Chlorpyrifos
2100:Azamethiphos
2062:Methoxychlor
1944:Thiamethoxam
1934:Paichongding
1919:Imidaclothiz
1914:Imidacloprid
1904:Clothianidin
1881:Pyriproxyfen
1861:Flufenoxuron
1851:Benzoylureas
1710:Butocarboxim
1679:Insecticides
1675:Pest control
1630:. Retrieved
1625:
1616:
1581:
1577:
1567:
1532:
1528:
1479:
1475:
1465:
1456:
1434:(1): 51–53.
1431:
1427:
1421:
1412:
1402:, retrieved
1397:
1387:
1366:
1336:(1): 26–32.
1333:
1329:
1322:
1297:
1293:
1286:
1272:cite journal
1247:
1243:
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931:Please help
919:
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886:epidemiology
883:
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769:Please help
757:
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662:Please help
650:
626:
613:deltamethrin
606:
590:
576:
564:
543:
539:
531:
524:
474:
470:
469:
61:Identifiers
51:
2777:Baculovirus
2729:Metabolites
2694:Sulfluramid
2496:Silafluofen
2463:Prallethrin
2443:Imiprothrin
2438:Fluvalinate
2428:Fenvalerate
2388:Cyhalothrin
2363:Acrinathrin
2355:Pyrethroids
2345:Trichlorfon
2210:Fosthiazate
2155:Dicrotophos
1939:Thiacloprid
1909:Dinotefuran
1899:Acetamiprid
1828:Paris Green
1735:Ethienocarb
1725:Carbosulfan
703:identify:
499:pyrethroids
481:used as an
418:Flash point
343:Properties
160:100.000.070
2860:Categories
2709:Veracevine
2640:Indoxacarb
2630:Fluralaner
2620:Fenoxycarb
2615:Fenazaquin
2610:Cyromazine
2590:Buprofezin
2570:Afoxolaner
2501:Tefluthrin
2491:Resmethrin
2458:Phenothrin
2453:Permethrin
2433:Flumethrin
2418:Etofenprox
2408:Empenthrin
2383:Cyfluthrin
2373:Bifenthrin
2368:Allethrins
2305:Quinalphos
2275:Phenthoate
2215:Isoxathion
2195:Fenamiphos
2180:Disulfoton
2175:Dioxathion
2170:Dimethoate
2150:Dichlorvos
2072:Tetradifon
2047:Heptachlor
2037:Endosulfan
1982:Cyclodiene
1929:Nithiazine
1924:Nitenpyram
1876:Methoprene
1866:Hydroprene
1793:Boric acid
1745:Isoprocarb
1740:Fenobucarb
1720:Carbofuran
1705:Bendiocarb
1687:Carbamates
1632:13 October
1578:Pediatrics
1404:2023-10-07
1157:2024-04-03
1133:2024-04-03
1109:2024-08-20
984:References
875:Smoothened
617:permethrin
603:Regulatory
593:pyrethroid
579:antagonist
495:pyrethrins
387:1.05 g/cm
373:Molar mass
244:LWK91TU9AH
133:ChemSpider
89:3D model (
68:CAS Number
2675:Adjuvants
2670:Sarolaner
2665:Pyriprole
2660:Pyridaben
2650:Lotilaner
2585:Bensultap
2549:Ryanodine
2486:Pyrethrum
2468:Pyrethrin
2285:Phosalone
2265:Parathion
2255:Omethoate
2235:Mevinphos
2220:Malathion
2135:Coumaphos
2110:Bensulide
2077:Toxaphene
1977:Chlordane
1871:Lufenuron
1765:Promecarb
1755:Metolcarb
1700:Aminocarb
1350:1879-0712
997:Carolina.
920:does not
758:does not
651:does not
547:head lice
527:pyrethrum
487:pesticide
181:200-076-7
173:EC Number
2845:Spinosad
2747:Paraoxon
2742:Malaoxon
2714:Xanthone
2689:Spinosad
2645:Limonene
2625:Fipronil
2554:Ryanodol
2526:Ryanoids
2340:Tribufos
2330:Terbufos
2315:Schradan
2205:Fenthion
2190:Ethoprop
2145:Diazinon
2095:Acephate
2032:Dieldrin
1967:Beta-HCH
1813:Cryolite
1770:Propoxur
1750:Methomyl
1715:Carbaryl
1695:Aldicarb
1608:21300677
1559:31642701
1506:22552772
1358:21172340
1264:18951417
1100:"ENDURA"
503:rotenone
483:adjuvant
412:Hazards
2683:Sesamex
2575:Amitraz
2320:Temefos
2310:R-16661
2290:Phosmet
2280:Phorate
2240:Mipafox
2165:Dimefox
2057:Lindane
2027:Dicofol
2002:1,2-DCE
1997:1,1-DCE
1992:1,4-DCB
1987:1,2-DCB
1599:3065142
1550:6867268
1497:3493191
1448:8132164
1314:5007655
1229:4919838
941:removed
926:sources
779:removed
764:sources
672:removed
657:sources
597:Sesamex
521:History
507:safrole
491:synergy
452:what is
450: (
383:Density
367:
211:PubChem
78:51-03-6
2876:Ethers
2595:Cartap
2295:Phoxim
2185:Ethion
2052:Kepone
2042:Endrin
1962:Aldrin
1760:Oxamyl
1606:
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1104:INCITE
1070:
1037:
501:, and
447:verify
444:
327:SMILES
199:C18880
113:ChEMBL
40:Names
2250:Naled
2067:Mirex
555:fleas
551:ticks
292:InChI
91:JSmol
2752:TCPy
2737:Oxon
2022:DFDT
1634:2020
1604:PMID
1555:PMID
1502:PMID
1444:PMID
1354:PMID
1346:ISSN
1310:PMID
1278:link
1260:PMID
1225:PMID
1068:ISBN
1035:ISBN
924:any
922:cite
762:any
760:cite
655:any
653:cite
536:Uses
235:UNII
224:5794
190:KEGG
142:5590
2017:DDT
2012:DDE
2007:DDD
1594:PMC
1586:doi
1582:127
1545:PMC
1537:doi
1533:127
1492:PMC
1484:doi
1480:128
1436:doi
1338:doi
1334:654
1302:doi
1252:doi
1217:doi
1190:doi
1060:doi
1027:doi
935:by
884:An
773:by
666:by
615:or
581:of
475:PBO
261:EPA
214:CID
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2478:;
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