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Home > Encyclopedia > Pyriproxyfen

Pyriproxyfen

Pyriproxyfen structure

Pyriproxyfen 

structure
  • CAS No:

    95737-68-1

  • Formula:

    C20H19NO3

  • Chemical Name:

    Pyriproxyfen

  • Synonyms:

    Pyridine,2-[1-methyl-2-(4-phenoxyphenoxy)ethoxy]-;2-[1-Methyl-2-(4-phenoxyphenoxy)ethoxy]pyridine;S 31183;Pyriproxyfen;S 9138;SK 591;BCP 8702;OMS 3019;Sumilarv;Tiger 10EC;Tiger (insecticide);Tiger;Admiral;S 71639;Nylar;Nemesis;Knack;Lano Tape;Esteem;Juventox;Distance;Seize;Pluto MC;Archer IGR;Distance IGR;NyGuard IGR;Juvinal;BRAI;BRAI 10EC;2-((1-(4-Phenoxyphenoxy)propan-2-yl)oxy)pyridine;126040-81-1;133695-78-0

  • Categories:

    Agrochemicals  >  Insecticides

Description

The pure product is crystal with m.p. being 45~47 ℃, the vapor pressure being 0.29 × 10-3Pa (20 ℃), and the relative density being 1.23 (20 ℃). Solubility: xylene 50%, hexane: 40%, and methanol: 20%. Gray to white crystalline solid or powder. Also described as a pale yellow, waxy solid or liquid. Commercial product is available as an emulsifiable concen- trate or wettable powders.


WHITE POWDER OR GRANULES


Pyriproxyfen is 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. It has a role as a juvenile hormone mimic. It is an aromatic ether and a member of pyridines. It derives from a 4-phenoxyphenol.

Pyriproxyfen Basic Attributes

321.37

321.37

429-800-1

1269

3077

DTXSID1032640

Colorless crystals|Pale yellow waxy solid (technical grade)|Pale yellow liquid

QP53AX73|QP53AC54

Characteristics

40.6

4.9

WHITE POWDER OR GRANULES

1.23 g/cm3 @ Temp: 20 °C

45-47 °C

230-250 °C @ Press: 0.2 Torr

119°C c.c.

1.5823 (20ºC)

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

0-6°C

Vapour pressure at 23°C: negligible

LD50 oral in rat: > 5gm/kg

Faint odor (technical grade)

Henry's Law constant = 6.3X10-10 atm-cu m/mole at 25 °C (est)

182.76 Ų [M+H]+ [CCS Type: TW]|184.43 Ų [M+H]+

Solidifies upon standing to give crystals (with mp at 49.7 °C)

Safety Information

III

9

UN30779/PG3

2

50/53

60-61

UT5804000

N

Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.

Stable under recommended storage conditions.

P273, P391, P501

H410

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.

Incompatible materials: Strong oxidizing agents

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/]

Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

|Warning|H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|Aggregated GHS information provided by 339 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Aggregated GHS information provided by 43 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Combustible. Liquid formulations containing organic solvents may be flammable.

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.

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.

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.

Nonirritating to skin, eye.

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.

Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.

NO open flames.

PREVENT DISPERSION OF DUST!

Use local exhaust.

Protective gloves.

Wear safety spectacles.

Pyriproxyfen was detected (>6.5 pg/cu m) in at least one of 54 air particulate samples collected Apr-July 2009 from three stations of the atmospheric monitoring network of the Regional Valencia Government, Spain(1).

Pyriproxyfen is listed as an ingredient in about 50 inside the home, pesticide and pet care products(1). Pyriproxyfen had dissipation half-lives from plants of 58 days under field conditions and 518-918 days under cold storage conditions(2).

Toxicity

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% ethanol, with or without pyriproxyfen or alum. Large doses of pyriproxyfen (9 or 15 mM) significantly enhanced specific total IgG immune response. This enhancement was no longer present 24 hr after treatment with pyriproxyfen. Moreover, pyriproxyfen induced higher titers of IgG2a and enhanced tumor necrosis factor-alpha and gamma-interferon responses. In a gene mutation assay (Ames Test)/Reverse Mutation, findings were determined as negative for induction of gene mutation measured in 5 S. typhimurium strains and E. coli WP2 uvra at doses from 10 to 5,000 ug/plate with and without metabolic activation. The highest does was insoluble. A gene mutation assay in mammalian cells was found to be negative for mutagencity in CHO (Chinese hamster ovary) V79 cells with and without metabolic activation up to cytotoxic doses (300 ug/mL). In a structural chromosomal aberration assay in vitro, findings proved nonclastogenic in CHO cells both with and without metabolic activation up to cytotoxic doses (300 ug/mL). ECOTOXICITY STUDIES: The impacts of pyriproxyfen on Daphnia magna reproduction was studied 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). Furthermore, pyriproxyfen decreases overall fecundity at all ages tested (7, 14, 21-d old female parthenogenic daphnids). Juvenile (3-d old) and reproductively mature (10-d old) female daphnids were also exposed to 155 pM pyriproxyfen for 2-12 d and reproduction measured for 16 d to compare the effects of short-term and prolonged exposures, and determine the potential for recovery. Results indicate that longer pyriproxyfen exposures (8-12 d) extend male production and decrease reproduction; however, daphnids exposed for only 2-4 d 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. The effect of pyriproxyfen on early ovary synthesis was examined in the Gecarcinid land crab, Gecarcoidea natalis. Pyriproxyfen may have stimulated early ovary development and induced synthesis of yolk protein by mimicking methyl farnesoate and thus causing endocrine disruption. The impact of the juvenile hormone analog pyriproxyfen on honeybee larvae and resulting adults within a colony was studied. Pyriproxyfen-treated bees emerged earlier than control bees and the highest dose led to a significant rate of malformed adults (atrophied wings). Young pyriproxyfen-treated bees were more frequently rejected by nestmates from the colony, inducing a shorter life span. This could be linked to differences in cuticular hydrocarbon profiles between control and pyriproxyfen-treated bees. Finally, pyriproxyfen-treated bees exhibited fewer social behaviors (ventilation, brood care, contacts with nestmates or food stocks) than control bees. Larval exposure to sublethal doses of pyriproxyfen affected several life history traits of the honeybees.

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.

LD50 Rat oral >5000 mg/kg|LD50 Rat percutaneous >2000 mg/kg|LC50 Rat inhalation >1300 mg/cu m/4 hr|LD50 Rabbit dermal >2,000 mg/kg

/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.

Pyriproxyfen's production may result in its release to the environment through various waste streams; its use as an insecticide(1) will result in its direct release to the environment(SRC).

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). [

Pyriproxyfen is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Pyriproxyfen does not contain chromophores that absorb at wavelengths >290 nm(1) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 1620 was calculated in fish for pyriproxyfen(SRC), using a log Kow of 5.37(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC).

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).

The Henry's Law constant for pyriproxyfen is estimated as 6.3X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that pyriproxyfen is expected to be essentially nonvolatile from water and moist soil surfaces(2). Pyriproxyfen is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of <9.8X10-8 mm Hg(3).

SURFACE WATER: Pyriproxyfen was detected in surface water samples collected July 19, 2005 at 0.02 and 0.01 ug/L in a waste water reservoir and coastal sea water about 1 hour before low tide off the coast of Kirishima City, Japan; pyriproxyfen was not detected (detection limit 0.01 ug/L) in any other of the samples collected (18 reservoir, 36 coastal collected June 21, 2005 and 17 reservoir, 35 coastal collected July 19, 2005)(1). Pyriproxyfen was detected in surface water samples from lakes (Volvi, Doirani, Kerkini) located in Northern Greece; samples were collected fall/winter 2010 and spring/summer 2011(2).

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).

Occupational exposure to pyriproxyfen may occur through inhalation and dermal contact with this compound at workplaces where pyriproxyfen is produced or used. Monitoring data indicate that the general population may be exposed to pyriproxyfen via inhalation of ambient air, ingestion of food containing insecticide residue, and dermal contact with consumer products containing pyriproxyfen. (SRC)

Drug Information

Treatment and prevention of flea infestations (Ctenocephalides felis) on cats.One application prevents flea infestation for one month. It also prevents the multiplication of fleas by inhibiting flea emergence in the environment of the cat for 3 months.|Treatment and prevention of flea infestation (Ctenocephalides felis and Ctenocephalides canis).Treatment and prevention of tick infestation (Rhipicephalus sanguineus, Dermacentor reticulatus, Ixodes ricinus).Prevention of biting from sand flies (Phlebotomus perniciosus), mosquitoes (Culex pipiens, Aedes aegypti) and stable flies (Stomoxys calcitrans).Treatment of mosquito (Aedes aegypti) and stable fly (Stomoxys calcitrans) infestation.

(VET): ... We report here 2 cases of pediculosis in random-source ponies. Infestation and clinical signs were not present during a 4-wk quarantine period or for 3 to 9 mo thereafter but became apparent coincident with the ponies' movement from pasture to indoor housing. These 2 geldings presented with pruritus associated with excoriating lesions on the neck, and infestation with Bovicola (Werneckiella) equi Denny, 1842 was diagnosed. Ponies were treated successfully with standard wound care and a spray containing 2.0% permethrin and 0.05% pyriproxyfen. These cases highlight the importance of recognizing the possibility of louse infestation, even in healthy, well-cared-for animals, and the need for personnel to be aware of early behavioral signs of infestation, such as rubbing and agitation.

Pesticides 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. (See all compounds classified as Insecticides.)

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.

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.

... 918 days for pyriproxyfen in pepper fruits under cold storage conditions. ...

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.

Fresh air, rest.


Rinse and then wash skin with water and soap.


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

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/SIGNS AND SYMPTOMS/ The substance may have effects on the blood and liver. This may result in anemia, impaired functions and tissue lesions.|/GENOTOXICITY/ ...In other 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).|/ALTERNATIVE and IN VITRO TESTS/ /This study/ evaluated the potential of pyriproxyfen to activate the ER by using an estrogen-responsive luciferase reporter gene in human ovarian carcinoma cells (E-CALUX assay system). Pyriproxyfen was reported to have some estrogenic activity with an EC10 of 2.9 x 10-5 M.

(+--)-pyriproxyfen

The substance can be absorbed into the body by ingestion and by inhalation of dust.

Cough.


No acute symptoms expected.


Redness.

Pyriproxyfen Use and Manufacturing

Methods of Manufacturing

The preparation of p-hydroxydiphenyl ether takes 4-bromodiphenyl ether as raw material, potassium hydroxide, copper powder and water are added, and the reaction is carried out under pressure at 245~250℃ for 16h, and then obtained by acidification, filtration, drying and vacuum distillation. The yield of p-hydroxydiphenyl ether is 81%. P-Hydroxydiphenyl ether can also be prepared by the following method. The preparation of 1-methyl-2-(4-phenoxyphenoxy) ethanol takes p-hydroxydiphenyl ether as raw material, adding 1-chloropropyl-2-ol, anhydrous potassium carbonate, DMF and phase transfer catalyst , Reacted at about 75 ℃ for 24h. The synthesis of mosquito ether uses DMF as a solvent, in the presence of sodium hydride, at room temperature, 1-methyl-2- (4-phenoxyphenoxy) ethanol and 2-chloropyridine, the reaction for 24h mosquito ether .

Uses

Insecticide.

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.

The WHO Recommended Classification of Pesticides by Hazard identifies pyriproxyfen as unlikely to present an acute hazard in normal use; Main Use: insecticide.

Pesticide or Metabolite (M) Common Name: Pyriproxyfen; Commodity: Almond hulls; Method Source: Valent; Method ID: RM-33H; Method Date: 9/17/97; Instrument: GC/NPD; Estimated LOQ (ppm): 0.10. /From table/|Pesticide or Metabolite (M) Common Name: Pyriproxyfen; Commodity: Apple pomace, ornage oil, oranges; Method Source: Valent; Method ID: RM-33P-1-3; Method Date: 11/20/96; Instrument: GC/NPD; Estimated LOQ (ppm): 0.02. /From table/|Pesticide or Metabolite (M) Common Name: Pyriproxyfen; Commodity: Butter, candy, flour, lettuce; Method Source: McLaughlin Gormley King; Method ID: PO594011; Method Date: 10/30/95; Instrument: HPLC/UV; Estimated LOQ (ppm): 0.08. /From table/|Pesticide or Metabolite (M) Common Name: Pyriproxyfen; Commodity: Cottonseed; Method Source: Valent; Method ID: RM-33P-2; Method Date: 5/21/96; Instrument: GC/NPD; Estimated LOQ (ppm): 0.02. /From table/|For more Analytic Laboratory Methods (Complete) data for PYRIPROXYFEN (11 total), please visit the HSDB record page.

To measure dermal exposure of a non-agricultural occupationally exposed population to pesticides, a new method has been developed for analysis of 13 pesticides from different classes (fungicides, herbicides, insecticides) on dermal patches. The method includes extraction of the patches and analysis of the pesticides by GC-MS and/or HPLC-fluorescence. Water-soluble pesticides (glyphosate and glufosinate) on patches were ultrasonically extracted twice with ultra-pure water for 10 min and analyzed by HPLC-fluorescence after derivatisation with FMOC. Organic-soluble pesticides (bifenthrin, cyprodinil, difufenicanil, fludioxonil, oxadiazon, pyriproxyfen, clopyralid, 2,4-D, fluroxypyr, 2,4-MCPA, and triclopyr) were extracted ultrasonically twice for 10 min with 70:30 dichloromethane-acetonitrile and analyzed by GC-MS directly or after derivatisation with N-methyl-N-tert-butyldimethylsilyltrifluoroacetamide. Detection limits varied between 3 and 4 ug/L for water-soluble pesticides and between 1 and 10 ug/L for organic-soluble pesticides.

Agrochemicals -> Insecticides|Veterinary drugs -> Vectra Felis -> EMA Drug Category|Antiparasitic products, insecticides and repellents, Other ectoparasiticides for topical use, pyriproxyfen, combinations -> Veterinary pharmacotherapeutic group|Veterinary drugs -> Vectra 3D -> EMA Drug Category|permethrin, combinations -> Veterinary pharmacotherapeutic group

Computed Properties

Molecular Weight:321.4
XLogP3:4.8
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:7
Exact Mass:321.13649347
Monoisotopic Mass:321.13649347
Topological Polar Surface Area:40.6
Heavy Atom Count:24
Complexity:338
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Price Analysis

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