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
Weitere Namen anzeigen
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
- Formalladung
- 0
- Komplexität
- 338
Experimentelle und physikochemische Eigenschaften
LogP
log Kow = 5.37
4.9
Density
1.24 at 25 °C
Density (at 20 °C): 1.14 g/cm³
Color/Form
Colorless crystals
Pale yellow waxy solid (technical grade)
Pale yellow liquid
Solubility
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)
Melting Point
47 °C
MP: 49.7 °C
48-50 °C
Vapor Pressure
0.00000218 [mmHg]
<9.8X10-8 mm Hg at 23 °C
Vapor pressure at 23 °C: negligible
Physical Description
Pale yellow liquid; Solidifies on standing; mp = 49.7 deg C; [Merck Index] Colorless solid; mp = 45-47 deg C; [ICSC] Colorless solid or pale yellow liquid; mp = 45-47 deg C; [HSDB] White crystalline solid; [MSDSonline]
WHITE POWDER OR GRANULES
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
- Löslichkeit
- 30 mg/ml; · DMF: 30 mg/ml; DMF:PBS(pH7.2) (1:2): 0.33 mg/ml; DMSO: 25 mg/ml; Ethanol: 15 mg/ml
- Aggregatzustand
- Solid
- pka
- 3.2 · 3.2 (base, est.)
- Wasserlöslichkeit
- 0.4 mg · 0.4 mg l-1 (25 °C)
- Farbe
- White to off-white
- Henry's Law Constant
- 1.6 · 1.6×104 mol/(m3Pa) at 25℃, HSDB (2015)
- Major Application
- agricultureenvironmental
- InChI
- InChI=1S/C20H19NO3/c1-16(23-20-9-5-6-14-21-20)15-22-17-10-12-19(13-11-17)24-18-7-3-2-4-8-18/h2-14,16H,15H2,1H3
- InChIKey
- NHDHVHZZCFYRSB-UHFFFAOYSA-N
- SMILES
- C1(OC(C)COC2=CC=C(OC3=CC=CC=C3)C=C2)=NC=CC=C1
- LogP
- 4.84 · 4.840 (est)
- CAS Datenbank
- 95737 · 95737-68-1(CAS DataBase Reference)
- NIST chemische Informationen
- Pyriproxyfen(95737-68-1)
- EPA chemische Informationen
- Pyriproxyfen (95737-68-1)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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
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
Special Reports
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/]
FIFRA Requirements
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.
Toxic Combustion Products
Special hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx)
Gives off irritating or toxic fumes (or gases) in a fire.
Hazard Classes and Categories
Aquatic Acute 1 (100%);Aquatic Chronic 1 (100%)
Aquatic Acute 1 (100%);Aquatic Chronic 1 (100%)
Hazardous to the aquatic environment (acute) - category 1;Hazardous to the aquatic environment (chronic) - category 1
Aquatic Acute 1;Aquatic Chronic 1
Sicherheit und Schutzausrüstung
First Aid Measures
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.
Fire Fighting Procedures
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
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
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.
Disposal Methods
SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.
Spillage Disposal
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. 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.
Preventive Measures
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.
Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.
Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.
Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
Toxikologische Informationen
Interactions
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
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
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
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).
Toxicity Summary
IDENTIFICATION AND USE: Pyriproxyfen could be solid or liquid. Pyriproxyfen is a potent insect growth regulator 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. It is also used as veterinary medication. HUMAN EXPOSURE AND TOXICITY: The substance may have effects on the blood and liver. This may result in anemia, impaired functions and tissue lesions. Pyriproxyfen was reported to have some estrogenic activity in human ovarian carcinoma cells. In genotoxicity assays, an increase in unscheduled DNA synthesis was not induced both with and without activation in HeLa cells exposed up to insoluble doses ranging to 6.4 ug/mL (without activation) and 51.2 ug/mL (with activation). ANIMAL STUDIES: Groups of 21 male and 21 female rats were fed diets containing pyriproxyfen at concentrations of 0, 80, 400, 2,000 and 10,000 ppm for 6 months. No death was found in any group. Alopecia in the neck and/or back, and soft feces were noticed in both sexes fed 10,000 ppm. A marked decrease in body weight gain was observed in both sexes fed 10,000 ppm throughout the treatment period, accompanying a decrease in food-consumption and an increase in water-intake during the initial stage of treatment. In organ weight, increases in liver (in males fed 2,000 ppm and 10,000 ppm, and in females fed 10,000 ppm), kidney (in both sexes fed 10,000 ppm) and thyroid (in females fed 10,000 ppm) and a decrease in pituitary (in females fed 2,000 and 10,000 ppm) were observed. Gross pathology revealed a higher incidence of blackish-brown coloration of the liver, and a lower incidence of accentuated lobular pattern of the liver (in males fed 10,000 ppm). An enlargement of the liver was seen in a few animals of both sexes fed 10,000 ppm. Mice were immunized thrice with ovalbumin in 5% e
Ecotoxicity Excerpts
/AQUATIC SPECIES/ ... Several candidate transcription factors were cloned from the water flea Daphnia pulex and evaluated for activation by methyl farnesoate. One of the factors evaluated, the complex of two bHLH-PAS proteins, dappuMet and SRC, activated a reporter gene in response to methyl farnesoate. Several juvenoid compounds were definitively evaluated for their ability to activate this receptor complex (methyl farnesoate receptor, MfR) in vitro and stimulate male sex determination in vivo. Potency to activate the MfR correlated to potency to stimulate male sex determination of offspring (pyriproxyfen>methyl farnesoate>methoprene, kinoprene). Daphnids were exposed to concentrations of pyriproxyfen and physiologic responses determined over multiple generations. Survival, growth, and sex of maternal organisms were not affected by pyriproxyfen exposure. Sex ratio among offspring (generation 2) were increasingly skewed in favor of males with increasing pyriproxyfen concentration; while, the number of offspring per brood was progressively reduced. Female generation 2 daphnids were reared to reproductive maturity in the absence of pyriproxyfen. Sex ratios of offspring (generation 3) were not affected in this pyriproxyfen lineage, however, the number of offspring per brood, again, was significantly reduced. ...
/AQUATIC SPECIES/ ... In this study, ...the impacts of pyriproxyfen on Daphnia magna reproduction /was investigated/ using a series of male production screening assays. These assays demonstrate that pyriproxyfen increases male production in a concentration-dependent fashion with an EC50 of 156 pM (50.24 ng/L); a concentration considered environmentally relevant. Furthermore, pyriproxyfen decreases overall fecundity at all ages tested (7, 14, 21-day old female parthenogenic daphnids). Juvenile (3-day old) and reproductively mature (10-day old) female daphnids were also exposed to 155 pM pyriproxyfen for 2-12 days and reproduction measured for 16 days to compare the effects of short-term and prolonged exposures, and determine the potential for recovery. Results indicate that longer pyriproxyfen exposures (8-12 days) extend male production and decrease reproduction; however, daphnids exposed for only 2-4 days recover and produce a relatively normal abundance of neonates. In addition, juvenile daphnids are also very sensitive to pyriproxyfen, but the primary effect on juvenile daphnids is reduced reproduction and protracted development not male production. Taken together, continued use of pyriproxyfen around water bodies needs due caution because of its potential adverse effects with significant developmental delays and male production compounded by prolonged exposure.
/AQUATIC SPECIES/ ... /In Daphnia magna, pyriproxyfen/ altered storage lipids in a concentration related manner enhancing ... their levels in post-spawning females. ...
/AQUATIC SPECIES/ ...A chronic full life-cycle test with Chironomus riparius from the first-instar larvae in the parental (P) generation until emergence in the subsequent F1 generation was conducted at different temperatures (16 and 24 °C), testing the effect of the insect growth regulator pyriproxyfen at 1, 3, 10, 30, and 100 ug/L. The emergence ratios were significantly affected by the interaction of temperature, chemical treatment, and generation, showing that, at lower temperatures, the negative effects of pyriproxyfen exposure were significantly greater in the F1 generation than in the P generation. The development rate showed that the effects of the interactions were significant in the F1 generation, underscoring the importance of extended exposure as a useful amendment to the risk assessment of those agrochemicals potentially influencing developmental and reproductive parameters in intact organisms. Moreover, results demonstrated that any difference from the standard temperature of 20 °C might result in additional stress, leading to disruption of biological functions in C. riparius, highlighting the interaction among different global climate change-related variables.
For more Ecotoxicity Excerpts (Complete) data for PYRIPROXYFEN (8 total), please visit the HSDB record page.
Signs and Symptoms
Cough.
No acute symptoms expected.
Redness.
No acute symptoms expected.
Ongoing Test Status
EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of July 7, 2016: http://actor.epa.gov/dashboard/]
ICSC Environmental Data
The substance is very toxic to aquatic organisms. Bioaccumulation of this chemical may occur in aquatic organisms. The substance may cause long-term effects in the aquatic environment. Avoid release to the environment in circumstances different to normal use.
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of pyriproxyfen can be estimated to be 1.2X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that pyriproxyfen is expected to be immobile in soil. In a field study, pyriproxyfen was shown to readily adsorb to organic matter(3). In leaching trials with four different soil types, over 50% of the pyriproxyfen remained in the upper 6 cm of a 30-cm soil column; there was no indication of rapid potential for downward migration(3).
Regulatorische Informationen
Regulatory Information
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
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
- safety_code
- 60-61
- hazard_class
- 9
- packing_group
- III
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 95737-68-1(Hazardous Substances Data)
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1
Chemie und Industrie
Pharmakologische Informationen
ATC Code
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
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.
Metabolism/Metabolites
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.
Absorption, Distribution and Excretion
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
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)
Formulations/Preparations
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.
Anwendungen
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.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
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.
Zugehörige Reaktionen
Verknüpfte Notizen
Wird geladen…