Pyriproxyfen

HCID 91753CAS 95737-68-1

Grundinformationen

Standard-SMILES
CC(COc1ccc(Oc2ccccc2)cc1)Oc1ccccn1
InChIKey
NHDHVHZZCFYRSB-UHFFFAOYSA-N
Summenformel
C20H19NO3
Durchschnittliche Molmasse
321,4 g/mol
Monoisotopische Masse
321,13649347

Namen und Bezeichner

Bevorzugter Name
Pyriproxyfen
IUPAC
2-[1-(4-phenoxyphenoxy)propan-2-yloxy]pyridine
Englischer Name
Pyriproxyfen
Summenformel
C20H19NO3
Molmasse
321.37

Namen und Synonyme

Pyriproxyfen95737-68-1Admiral2-[1-Methyl-2-(4-phenoxyphenoxy)ethoxy]pyridineNylar2-((1-(4-Phenoxyphenoxy)propan-2-yl)oxy)pyridinejuvinalDistanceSumilarvEsteemNemesisKnack
Weitere Namen anzeigen
PYRIPROXIFENPyriproxyfes9138s31183S 9318SK-591LANO(R)ADEAL(R)KNACK(R)
Lano TapeArcher IGRNyGuard IGRPluto MCDistance IGRTiger 10EC4-Phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl etherDTXSID1032640

Datenbank-Bezeichner

CAS
95737-68-1
PubChem CID
91753
DTXSID
DTXSID1032640
ChEMBL
CHEMBL1883234
ChEBI
CHEBI:39260
UNII
3Q9VOR705O
EC Number
429-800-1、619-166-6
Nikkaji
J227.495G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,8
Polarare Oberfläche (TPSA)
40,6 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
7
Schwere Atome
24

Experimentelle und physikochemische Eigenschaften

LogP · 2 Einträge

log Kow = 5.37

4.9

TasteFaint odor (technical grade)
Density · 2 Einträge

1.24 at 25 °C

Density (at 20 °C): 1.14 g/cm³

Color/Form · 3 Einträge

Colorless crystals

Pale yellow waxy solid (technical grade)

Pale yellow liquid

Solubility · 2 Einträge

In hexane 400, methanol 200, xylene 500 (all g/kg at 20-25 °C)

Solubility in water, mg/l at 20 °C: 0.101 (practically insoluble)

Flash Point119 °C c.c.

Physikochemische Eigenschaften

Schmelzpunkt
45 · 45-47°C
Siedepunkt
230 · 230-250 °C(Press: 0.2 Torr)
Dichte
1.32 · 1.32
Dampfdruck
2.9 x · 2.9 x l0-4 Pa (20 °C)
Brechungsindex
20.5 · nD20.5 1.5823
storage temp.
0 · 0-6°C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P273, P391, and P501 (click each P-code to see the statement)

Warning

Gefahrenhinweise

Regulatory Information · 5 Einträge

Commission Regulation No 844/2012

Pyriproxyfen is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2010/39/EU, Reg. (EU) 2018/1796, Reg. (EU) 2019/1589, Reg. (EU) 2020/968, Reg. (EU) No 540/2011

Status: Active Update: 10-11-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/9704

Pyriproxyfen: HSNO Approval: HSR003297 Approved with controls

Fire HazardsCombustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.
Fire PotentialCombustible. Liquid formulations containing organic solvents may be flammable.
Hazards SummaryMay have effects on the blood and liver; [ICSC]
UN ClassificationUN Hazard Class: 9; UN Pack Group: III
Special Reports · 1 Eintrag

USEPA/OPP; EDSP: Weight of Evidence Analysis of Potential Interaction with the Estrogen, Androgen or Thyroid Pathway for Pyriproxyfen (95737-68-1) (2015). The Endocrine Disruptor Screening Programs (EDSP) Tier 1 assay battery is designed to provide the necessary empirical data to evaluate the potential of chemicals to interact with the estrogen (E), androgen (A) or thyroid (T) signaling pathways. This interaction includes agonism and antagonism at the estrogen and androgen receptors, altered steroidogenesis, as well as hypothalamic-pituitary-gonadal (HPG) and hypothalamic-pituitary thyroid (HPT) perturbations. In addition to the available Tier 1 data, other scientifically relevant information (OSRI), including, general toxicity data and open literature studies of sufficient quality were considered in this assessment.[Available from, as of June 29, 2016: https://www3.epa.gov/]

Sicherheit und Schutzausrüstung

Fire FightingUse water spray, powder, foam, carbon dioxide.
First Aid Measures · 4 Einträge

Fresh air, rest.

Rinse and then wash skin with water and soap.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth.

Safe StorageSeparated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.
Fire Fighting Procedures · 2 Einträge

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical, or carbon dioxide.

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Storage Conditions · 2 Einträge

Keep container tightly closed in a dry and well-ventilated place.

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Well closed.

Cleanup Methods · 2 Einträge

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT wash away into sewer.

Toxikologische Informationen

Interactions · 1 Eintrag

A number of pesticides are used in agricultural production with some having estrogenic activities, such as endocrine-disrupting chemicals that may affect wildlife and humans. This study aimed to detect the estrogenic effects of some mixed agricultural chemicals in agricultural production. The assay to measure estrogenic activity was evaluated by the cell proliferative activity of MtT/Se cells, which respond well to estrogen. To evaluate MtT/Se cells we went down to the molecular level of estrogen receptor (ER)-alpha and ER-beta expression. The proportion of ER-alpha to ER-beta was 3.55:1, as determined by semi-quantitative real-time PCR. These results showed that ER-alpha was dominant in MtT/Se cells on the transcriptional level, therefore implying that the estrogenic activity detected by these cells may be mainly mediated by ER-alpha. It was found that ... pyriproxyfen ... had estrogenic activity. Several pesticides are often present in agricultural products. Therefore, we evaluated the estrogenic activity of a mixture of two pesticides. The REC(10) levels of prothiofos/pyriproxyfen and thiabendazole/orthophenylphenol were increased up to 10-fold. We concluded that those two pesticide combinations showed a significantly higher estrogenic effect in comparison to the results of the respective pesticides when tested individually.

Ecotoxicity Values · 5 Einträge

LC50; Species: Daphnia carinata sensu lato /Cladoceran/; Concentration: 0.08 ppm for 48 hr /Conditions of bioassay not specified/

LC50; Species: Leander tenuicornis (shrimp); Concentration: 0.098 ppm for 96 hr /Conditions of bioassay not specified/

EC50; Species: Daphnia magna (Water flea) age 6-7 days female; Conditions: freshwater, renewal, 20 °C; Concentration: 149 ug/L for 60 hr; Effect: genetics, increased 2-domain hemoglobin mRNA /formulation/

EC50; Species: Daphnia magna (Water Flea) age >13 day, mature organism; Conditions: freshwater, renewal, 20 °C; Concentration: 0.0557 ug/L for 5 days; Effect: population, change sex ratio /formulation/

For more Ecotoxicity Values (Complete) data for PYRIPROXYFEN (9 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.2X10+5(SRC), determined from a structure estimation method(2), indicates that pyriproxyfen is expected to be immobile in soil(SRC). Volatilization of pyriproxyfen from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.3X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Pyriproxyfen is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of <9.8X10-8 mm Hg at 23 °C(3). Biodegradation data in soil were not available(SRC, 2016).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.2X10+5(SRC), determined from a structure estimation method(2), indicates that pyriproxyfen is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 6.3X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Pyriproxyfen is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(4), an estimated BCF of 1620(SRC), from its log Kow of 5.37(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). Biodegradation data in water were not available(SRC, 2016).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pyriproxyfen, which has a vapor pressure of <9.8X10-8 mm Hg at 23 °C(2), will exist solely in the particulate phase in the ambient atmosphere. Particulate-phase pyriproxyfen may be removed from the air by wet and dry deposition(SRC). Pyriproxyfen does not contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). [

Food Survey Values · 1 Eintrag

Agricultural products monitored in Hyogo Prefecture, Japan from April 1995 to March 2000, found pyriproxyfen in 4 of 60 imported orange samples at concentrations of <0.05 ug/g, but was not detected in any of the other 227 imported and 478 domestic products sampled(1). Of 173 agricultural products analyzed in 2006 from Japan, two were reported to contain pyriproxyfen at 13 and 16 ng/g(2). Pyriproxyfen was detected in soya-based nutraceutical products at a maximum of 1.5 ug/kg(3).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesThe substance can be absorbed into the body by ingestion and by inhalation of dust.

Regulatorische Informationen

Regulatory Information · 5 Einträge

Commission Regulation No 844/2012

Pyriproxyfen is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2010/39/EU, Reg. (EU) 2018/1796, Reg. (EU) 2019/1589, Reg. (EU) 2020/968, Reg. (EU) No 540/2011

Status: Active Update: 10-11-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/9704

Pyriproxyfen: HSNO Approval: HSR003297 Approved with controls

FIFRA Requirements · 3 Einträge

Tolerances are established for residues of pyriproxyfen, including its metabolites and degradates, in or on the commodities in the following table. Compliance with the tolerance levels specified is determined by measuring only pyriproxyfen, 2-[1-methyl-2-(4-phenoxyphenoxy) ethoxy]pyridine, in or on the commodity.[Table#6687]

A tolerance ... is established for all food commodities as a result of the proposed use of NYLAR in food handling establishments where food and food products are held, prepared, processed or served. Application is limited to space, general surface, spot, and/or crack and crevice treatment in food handling establishments where food and food products are held, processed, prepared and served. Space and general surface application may be used only when the facility is not in operation provided exposed food is covered or removed from the area being treated prior to application. Spot, and/or crack and crevice treatment may be used while the facility is in operation provided exposed food is covered or removed from the area being treated prior to application. Food contact surfaces should be thoroughly washed with an effective cleaning compound and rinced with potable water after use of the product. To assure safe use of this additive, its label and labeling shall conform to that registered with the U.S. Environmental Protection Agency, and shall be used in accordance with such label and labeling.

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 129032; Type of Pesticide: conventional insecticide; Use Site: food use and non-food use; Year: 1995.

Sicherheitsdaten

wgk
2
ridadr
UN3077 9/PG 3
RTECS-Nr.
UT5804000
risk_code
50/53
Toxizität
LD50 oral in rat: > 5gm/kg
hazard_code
N

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 1 Eintrag

QP - Antiparasitic products, insecticides and repellents;QP53 - Ectoparasiticides, insecticides and repellents;QP53A - Ectoparasiticides for topical use, incl. insecticides;QP53AX - Other ectoparasiticides for topical use;QP53AX23 - Pyriproxyfen

Mechanism of Action · 1 Eintrag

Pyriproxyfen mimics insect juvenile growth hormone, halting development during metamorphosis and larval development. It also concentrates in female flea ovaries, causing non-viable eggs to be produced. When combined with an adulticide (e.g., permethrin, fipronil) all stages of the parasite are killed and re-infestation is less likely.

Biological Half-Life... 918 days for pyriproxyfen in pepper fruits under cold storage conditions. ...
Metabolism/Metabolites · 3 Einträge

The metabolic fate of pyriproxyfen (4-phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl ether, Sumilarv) was examined in rats and mice given single oral doses of (pyridyl-2,6-(14)C)- or (phenoxyphenyl-(14)C)pyriproxyfen at doses of 2 and 1000 mg/kg. The carbon-14 was excreted almost completely into urine and feces within 7 days after dosing and fecal excretion of carbon-14 predominated in both animals. Excretion of carbon-14 into feces and urine was, respectively, 84-97% and 4-12% of the dose in rats and 64-91% and 9-38% in mice. Major metabolic reactions of pyriproxyfen were (1) hydroxylation at the 4-position of the terminal phenyl ring, (2) hydroxylation at the 2-position of the terminal phenyl ring, (3) hydroxylation at the 5-position of the pyridyl ring, (4) dephenylation, (5) cleavage of ether linkages, and (6) conjugation of the resultant phenols with sulfate or glucuronate. Although there was generally no marked difference in the metabolic profile of pyriproxyfen between the two species, significant sex-related differences were found in metabolic reactions 1, 3, and 6 in the rat but not in the mouse.

Levels of cytochrome P450 and b5 were investigated in microsomal enzymes of houseflies from the gut and fat body of the third instar larvae of a pyriproxyfen-resistant strain (YPPF) and two pyriproxyfen-susceptible strains (YS and SRS). In comparison to the YS and SRS strains, YPPF microsomes had higher levels of total cytochrome P450s in both the gut and fat body. Furthermore, microsomes from the gut and fat body of YPPF larvae were found to have a much greater ability to hydroxylate aniline than YS larvae. In vitro metabolism studies of pyriproxyfen indicated that the metabolic rates were much higher in both the gut and fat body of YPPF larvae than of YS and SRS larvae. The major metabolites of pyriproxyfen in houseflies were identified to be 4'-OH-pyriproxyfen and 5"-OH-pyriproxyfen. Cytochrome P450 inhibitors, piperonyl butoxide (PB) and 2-propynyl 2,3,6-trichlorophenyl ether (PTPE), decreased the metabolic rates significantly in all three strains. This study confirmed that microsomal cytochrome P450 monooxygenases play an important role in the pyriproxyfen resistance of the housefly. Furthermore, it suggests that the fat body must be as important as the gut for the metabolism of pyriproxyfen in resistant housefly larvae.

... Rats were orally dosed with (14)C-labeled pyriproxyfen at 2 or 1,000 mg/kg and at repeated oral doses (14 daily doses) of unlabeled pyriproxyfen at 2 mg/kg followed by admin of a single oral dose of labeled pyriproxyfen at 2 mg/kg. ...Examination of urine, feces, liver, kidney, bile, and blood metabolites yielded numerous (>20) identified metabolites when compared to synthetic standards. The major biotransformation reactions of pyriproxyfen include: (i) Oxidation of the 4' - position of the terminal phenyl group; (ii) Oxidation at the 5' - position of pyridine; (iii) Cleavage of the ether linkage and conjugation of the resultant phenols with sulfuric acid.

MeSH Pharmacological ClassificationPesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
Absorption, Distribution and Excretion · 2 Einträge

Male and female rats were given a single oral dose of ... ((14)C)pyriproxyfen /labeled on the phenoxyphenyl moiety/ <4-phenoxyphenyl(R,S)-2-(2-pyridyloxy)propyl ether> at 2 (low dose) or 1000 (high dose) mg/kg. (14)C was rapidly excreted into feces and urine, with the former route predominating (about 90% of the dose). Peak (1)4C concentrations in blood, kidney, liver, and other tissues except for fat occurred 2-8 hr after administration, being 0.4, 0.4, 2.5, and <0.2 g of pyriproxyfen equivalents/g of tissue (ppm), respectively. Peak (14)C concentration in fat occurred 12-24 hr after administration, being 0.3-0.5 ppm. (14)C tissue residues on the seventh day were below 0.02 and 10 ppm for the low and high doses, respectively. ... No marked sex-related differences were observed for (14)C excretion or (14)C tissue residues. However, a slight sex-related variation was found for the extent of metabolic reactions.

... Rats were orally dosed with (14)C-labeled pyriproxyfen at 2 or 1,000 mg/kg and at repeated oral doses (14 daily doses) of unlabeled pyriproxyfen at 2 mg/kg followed by admin of a single oral dose of labeled pyriproxyfen at 2 mg/kg. Most radioactivity was excreted in the feces (81-92%) and urine (5-12%) over a 7-day collection period. ... /Radioactivity/ was not detected /in expired air/. Tissue radioactivity levels were very low (< 0.3%) except for fat. Examination of urine, feces, liver, kidney, bile, and blood metabolites yielded numerous (>20) identified metabolites when compared to synthetic standards.

Verwendung und Herstellung

Uses · 6 Einträge

Used as insect growth regulator to control public health pests; [HSDB] Used as insecticide and veterinary ectoparasiticide; [Merck Index] Used as an insecticide to protect tomato, eggplant (aubergine), and cotton plants; [EFSA: Pyriproxyfen - 2009]

Farming (Pesticides) [Category: Industry]

For pyriproxyfen (USEPA/OPP Pesticide Code: 129032) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state, and local authorities must be consulted for currently approved uses./

Insect growth regulator.

Pyriproxyfen is a potent JH mimic affecting the hormonal balance in insects, thereby resulting in strong suppression of embryogenesis, metamorphosis, and adult formation. It is used to control agricultural, veterinary, and human health pests such as whiteflies and scale insects; flies, mosquitoes, and fleas.

MEDICATION (VET)

Methods of ManufacturingPreparation: S. Nishida et al., United Kingdom patent 2140010; eidem, United States of America patent 4751225 (1984, 1988 both to Sumitomo)
Formulations/Preparations · 5 Einträge

The National Pesticide Information Retrieval System (NPIRS) identifies 31 companies with active labels for products containing the chemical pyriproxyfen. To view the complete list of companies, product names and percent pyriproxyfen in formulated products click the following url and enter the CAS Registry number in the Active Ingredient field.

Sergeant's Insecticide Carpet Powder with Nylar (Sergeant's Pet Care Products, Inc.): Active ingredient: MGK 264 0.5%; Pyrethrins 0.1%; and Pyriproxyfen 0.1%.

Sergeant's Dog Shampoo (Sergeant's Pet Care Products, Inc.): Active ingredient: MGK 264 0.5%; Permethrin 0.1%; and Pyriproxyfen 0.01%.

Supra-Quick Mist with IGR (Sergeant's Pet Care Products, Inc.): Active ingredient: MGK 264 0.33%; Piperonyl butoxide 0.2%; Pyrethrins 0.1%; and Pyriproxyfen 0.005%.

For more Formulations/Preparations (Complete) data for PYRIPROXYFEN (27 total), please visit the HSDB record page.

Household ProductsInformation on 88 consumer products that contain Pyriproxyfen in the following categories is provided:;• Inside the Home;• Pesticides;• Pet Care
General Manufacturing InformationThe WHO Recommended Classification of Pesticides by Hazard identifies pyriproxyfen as unlikely to present an acute hazard in normal use; Main Use: insecticide.
Anwendungen · 2 Einträge

BeschreibungPyriproxyfen is a pyridine compound and, in common with fenoxycarb, is a juvenile hormone mimic whose structure is unrelated to natural juvenile hormone. It is an insect growth regulator. Fleas absorb pyriproxyfen either by direct contact or by ingesting blood from a treated animal.

VerwendenPyriproxyfen is a pyridine-based pesticide used against a variety of arthropoda, in particular to protect cotton crops against whitefly.

Anbieter50 Anbieter

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: An aromatic ether that consists of propylene glycol having a 2-pyridyl group at the O-1 position and a 4-phenoxyphenyl group at the O-3 position.

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