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Pyridalyl

Pyridalyl structure

Pyridalyl 

structure
  • CAS No:

    179101-81-6

  • Formula:

    C18H14Cl4F3NO3

  • Chemical Name:

    Pyridalyl

  • Synonyms:

    Pyridine,2-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-5-(trifluoromethyl)-;Pyridine,2-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propenyl)oxy]phenoxy]propoxy]-5-(trifluoromethyl)-;2-[3-[2,6-Dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-5-(trifluoromethyl)pyridine;Pyridalyl;S 1812;Tesoro;Overture;Pleo;229971-56-6

  • Categories:

    Analytical Chemistry  >  Standard

Description

Pyridalyl is an organochlorine insecticide, an organofluorine insecticide and a dichlorobenzene.

Pyridalyl Basic Attributes

491.12

491.12

605-845-4

QTD92Z2P2Z

DTXSID8034875

Liquid

Characteristics

40.6

7.59 (est)

1.44 at 20 deg C

227 deg C (decomposes)

283.7ºC

1.544

In water, 150 mg/L at 20 deg C

0-6°C

6.24X10-5 mPa /SRC: 4.68X10-10 mm Hg/ at 20 deg C

Henry's Law constant = 2.0X10-12 atm-cu m/mole at 20 °C (est)

Safety Information

P260, P261, P272, P273, P280, P302+P352, P314, P321, P333+P313, P363, P391, P501

H317

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. 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 soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.|PESTICIDE DISPOSAL. Waste resulting from the use of this product may be disposed of on site or at an approved waste disposal facility. Do not contaminate water, food or feed by storage, disposal or cleaning of equipment. Open dumping is prohibited. /Overture 35 WP Insecticide/|CONTAINER DISPOSAL. Nonrefillable container. Do not reuse or refill the outer bag. Dispose of outer bag in a sanitary landfill or by incineration, or if allowed by State and local authorities, by burning. If burned, stay out of smoke. /Overture 35 WP Insecticide/|Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal. /Residential users/|Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it. /Residential users/

|Warning|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P260, P261, P272, P273, P280, P302+P352, P314, P321, P333+P313, P363, P391, and P501|Aggregated GHS information provided by 158 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Applicators and other handlers must wear: long-sleeved shirt and long pants, waterproof gloves, shoes plus socks. /Overture 35 WP Insecticide/|... Restricted entry interval (REI) of 12 hours. PPE required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, or water, is: coveralls, waterproof gloves and shoes plus socks. /Overture 35 WP Insecticide/

FIRE FIGHTING INSTRUCTIONS: Products of combustion from fires involving this material may be toxic. Avoid breathing smoke and mists. Avoid personnel and equipment contact with fallout and runoff. Minimize the amount of water used for fire fighting. Do not enter any enclosed area without full protective equipment, including self-contained breathing equipment. Contain and isolate runoff and debris for proper disposal. Decontaminate personal protective equipment and fire fighting equipment before reuse. /Overture 35 WP Insecticide/

Do not contaminate water when disposing of equipment wash water or rinsate. /Overture 35 WP Insecticide/|ACCIDENTAL RELEASE MEASURES. FOR SPILLS ON LAND: CONTAINMENT: Reduce airborne dust. Avoid runoff into storm sewers or other bodies of water. CLEANUP: Clean up spill immediately. Vacuum or sweep up material and place in a chemical waste container. Wash area with soap and water. Pick up wash liquid with additional absorbent and place in a chemical waste container. /Overture 35 WP Insecticide/|ACCIDENTAL RELEASE MEASURES. FOR SPILLS IN WATER: CONTAINMENT: This material will disperse or dissolve in water. Stop the source of the release. Contain and isolate to prevent further release into soil, surface water and ground water. CLEANUP: Clean up spill immediately. Absorb spill with inert material. Remove contaminated water for treatment or disposal. /Overture 35 WP Insecticide/|If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label./Residential users/|After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide. To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash. /Residential users/

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR part 170. /Overture 35 WP Insecticide/|This pesticide is toxic to fish and invertebrates. Do not apply directly to water, to areas where surface water is present, or to intertidal areas below the mean high water mark. /Overture 35 WP Insecticide/|Do not apply this product in a way that will contact workers or other persons, either directly or through drift. Only protected handlers may be in the area during application /Overture 35 WP Insecticide/|Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 12 hours. /Overture 35 WP Insecticide/|For more Preventive Measures (Complete) data for Pyridalyl (13 total), please visit the HSDB record page.

Toxicity

/AQUATIC SPECIES/ The most sensitive benthic invertebrate species tested was Asellus aquaticus which is an isopod. Reduced abundance in Asellus aquaticus was observed in a microcosm study that applied 4 applications of pyridalyl to overlying water at 0.05 ug/L and higher... . Therefore, a single application of pyridalyl could impact Asellus and other species that are as sensitive as Asellus. Effects (reduced emergence, reduced abundance) have also been observed in chironomids in several studies.

Pyridalyl'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), a Koc value range of 402,000 to 2,060,000(2) indicates that pyridalyl is expected to be immobile in soil(SRC). Volatilization of pyridalyl from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.0X10-12 atm-cu m/mole(SRC), based upon its vapor pressure, 4.68X10-10 mm Hg(2), and water solubility, 150 mg/L(2). Pyridalyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). The major route of degradation for pyridalyl in laboratory studies was photodegradation in soil(3). Pyridalyl degraded in an aerobic soil metabolism study with half-lives of 93.7 to 346.6 days and had half-lives of 46.2 days to 256 days in several terrestrial field dissipation studies(3).|AQUATIC FATE: Based on a classification scheme(1), a Koc value range of 402,000 to 2,060,000(2) indicates that pyridalyl 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 2.0X10-12 atm-cu m/mole(SRC), derived from its vapor pressure, 4.68X10-10 mm Hg(2), and water solubility, 150 mg/L(2). According to a classification scheme(4), a BCF of >16,000 in bluegill sunfish(5), suggests bioconcentration in aquatic organisms is very high(SRC). The major route of degradation for pyridalyl in laboratory studies was photodegradation with a reported half-life of 2 to 6 days, however in environmental conditions other than clear, shallow and low organic matter water, aquatic photodegradation is not likely(5). Pyridalyl is reported as stable to hydrolysis(5). In an aerobic aquatic metabolism study pyridalyl degraded with half-lives of 128.4 to 203.9 days and in an anaerobic aquatic metabolism study, pyridalyl degraded with a half-life of 370 days in the whole system(5).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pyridalyl, which has a vapor pressure of 4.68X10-10 mm Hg at 20 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase pyridalyl may be removed from the air by wet or dry deposition(SRC).

The major route of degradation for pyridalyl in laboratory studies was photodegradation in water and soil(1). Photodegradation in water had a reported half-life of 2 to 6 days; however, in environmental conditions other than clear, shallow and low organic matter water, aquatic photodegradation is not likely. Pyridalyl is reported as stable to hydrolysis(1).

A 49 day BCF in bluegill sunfish had a reported whole fish BCF of >16,000 and an estimated steady state BCF of approximately 27,000(1). According to a classification scheme(2), this BCF suggests bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC).

Pyridalyl has reported Kd values of 2473 to 3848 with corresponding Koc values of 402,000 to 2,060,000(1). According to a classification scheme(2), this estimated Koc value range suggests that pyridalyl is expected to be immobile in soil.

The Henry's Law constant for pyridalyl is estimated as 2.0X10-12 atm-cu m/mole(SRC) derived from its vapor pressure, 4.68X10-10 mm Hg(1), and water solubility, 150 mg/L(1). This Henry's Law constant indicates that pyridalyl is expected to be essentially nonvolatile from water and moist soil surfaces(2). Pyridalyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Occupational exposure to pyridalyl may occur through inhalation of dust and dermal contact with this compound at workplaces where pyridalyl is produced or used. Use data indicate that the general population may be exposed to pyridalyl via insecticidal use on ornamentals. (SRC)

Drug Information

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.)

Groups of 3 Sprague-Dawley (Crl:CDBR) rats/sex/group were dosed with pyridalyl of high purity, to which labeled pyridalyl (either phenyl or propenyl-labeled) pyridalyl of at least 97% purity was added to achieve 5 or 500 mg/kg single gavage doses at 50 uCi/rat. The study evaluated radioactivity in many tissues sampled at 4 times (based on results of Record No. 242040): 1/2 Cmax (absorption), Cmax, 1/2 Cmax (elimination), and 1/10 Cmax (elimination). These sampling times were 4, 8, 24, and 48 hrs for 5 mg/kg phenyl label, 6, 8, 24, and 48 hrs for 500 mg/kg phenyl label, 4, 12, 48, and 120 hrs for 5 mg/kg propenyl label, and 6, 12, 72, and 120 hrs for 500 mg/kg propenyl label. Five tissues were evaluated for extractable residues: liver, kidney, lung, blood, and fat. Major metabolites were evaluated in these tissues. Whole blood label diminished an order of magnitude as expected, from Cmax to 1/10 Cmax (elimination) in the case of low dose males and females administered phenyl label, and in low dose males administered the propenyl label. In other cases, it appeared that the estimate of 1/10 Cmax (elimination) was premature. Label persisted longest in fat (regardless of gender, dose, or label position): often showing a higher concentration at estimated 1/10 Cmax (elimination) than at Cmax. In general, adrenal radiolabel was higher than in tissues other than fat during the elimination phase. Some other tissues, such as thyroids, pancreas, and ovaries, often had radiolabel content higher than most other tissues during elimination phase, but differences were typically small and variable. Of the five tissues evaluated for extractable residues, fat was unique in that label was consistently highly extractable, and composed nearly all of parent pyridalyl, regardless of gender, dose, or label placement. Initially [1/2 Cmax (absorption)], over 91% of label in each of the 5 assessed tissues was extractable following phenyl-label treatment. Extractability for low-dose phenyl groups at 1/10 Cmax (elimination) for tissues other than fat ranged from 69% upward without obvious differences between tissues. Percent extractability for high-dose phenyl groups at 1/10 Cmax (elimination) was generally over 90%. Percent extractability of propenyl label at 1/2 Cmax (absorption) ranged from 74% to 95%, but dropped for all tissues over time, so that extractability at 1/10 Cmax (elimination) was 37% to 53% for liver and kidney, 53-67% for lung, but very low for blood (21-22% extractable for low dose propenyl groups, and a constant 0% for high dose propenyl groups). Parent pyridalyl was the major component of residues in liver, kidney, lung, blood, and fat during the early absorption process of phenyl-labeled test article. The percentage of pyridalyl label during elimination varied greatly. Liver retained only small amounts of pyridalyl at 1/10 Cmax (less than 10% of radiolabel), whereas fat still contained 95- 100% of radiolabel as pyridalyl at that time. Parent pyridalyl was typically the dominant component of lung and kidney through 1/10 Cmax.

Groups of 3 Sprague-Dawley (Crl:CDBR) rats/sex/group were dosed with pyridalyl of high purity, to which labeled pyridalyl (either phenyl or propenyl-labeled) pyridalyl of at least 97% purity was added to achieve 5 or 500 mg/kg single gavage doses at 50:Ci/rat. The study evaluated radioactivity in many tissues sampled at 4 times (based on results of Record No. 242040): 1/2 Cmax (absorption), Cmax, 1/2 Cmax (elimination), and 1/10 Cmax (elimination). These sampling times were 4, 8, 24, and 48 hrs for 5 mg/kg phenyl label, 6, 8, 24, and 48 hrs for 500 mg/kg phenyl label, 4, 12, 48, and 120 hrs for 5 mg/kg propenyl label, and 6, 12, 72, and 120 hrs for 500 mg/kg propenyl label. Five tissues were evaluated for extractable residues: liver, kidney, lung, blood, and fat. Major metabolites were evaluated in these tissues. The major metabolite in liver by 1/10 Cmax was the product of degradation of the dichloropropenyl group to yield the corresponding phenoxyacetic acid (designated S-1812-PhCH2COOH). ... The major metabolite in liver by 1/10 Cmax was the product of degradation of the dichloropropenyl group to yield the corresponding phenoxyacetic acid (designated S-1812-PhCH2COOH). This same acid was typically a major component of blood, particularly in the elimination phase. Blood also carried large and variable amounts of uncharacterized polar components. One more characterized metabolite was relatively important in phenyl labeling experiments: S-1812-DP (loss of the dichloropropenyl group to yield a phenol). S-1812-DP occasionally constituted over 20% of extracted radiolabel, and had no strong proclivity for any one tissue. A comparatively minor characterized metabolite was HPHM [loss of the trifluoropyridine group, with the balance of parent unchanged]. HPHM rarely exceeded a few percent of extractable radiolabel, and often was below detection limits. Label placement in the propenyl substituent led to increased percent of recovered label in the highly polar fraction.|Groups of 4 Sprague-Dawley (Crl:CDBR) rats/sex were dosed once by gavage in corn oil vehicle. There were low-dose and high dose groups at 5 and 500 mg/kg/day, respectively, with 14C label placement in phenyl and propenyl groups, and 5 mg/kg/day only for label placement in the pyridyl group. Investigators evaluated excreta for metabolites, and quantified expired CO2 over time. Tissues were examined for radioactivity after 168 hrs. About 90% of recovered radioactivity following phenyl- or pyridyl-labeled pyridalyl was found in feces, with about 2% in urine, and the balance of recovered radioactivity was found in tissues (about 1%), and carcass (up to 4%). There was no remarkable dose effect. No CO2 was obtained from phenyl- or pyridyl-labeled material. In contrast, propenyl-label led to 11-12% in expired air as CO2, in addition to 55-59% of label in feces, 10-18% in urine, 2% in tissues, and 4-8% in carcass. Analyses of excreted products did not indicate sex differences in disposition, however the extent of metabolism of pyridalyl was typically reduced at the higher dose levels. Low dose exposure to either phenyl or pyridyl label led to 31-39% of administered label in parent pyridalyl, 42-51% of label as S-1812-DP (loss of the dichloropropenyl group to yield a phenol), about 2% of label as S-1812-Py-OH (hydroxy substituent added to pyridyl ring), and up to 4-7% of administered dose as HPHM (loss of the pyridyl ring: relevant in the case of low dose phenyl-label). High dose exposure to phenyl label led to about 50% of administered label as parent pyridalyl and only 25-29% of label as S-1812-DP. Cleavage of the pyridyl ring after pyridyl-label administration yielded 2-hydroxy-5-trifluoromethylpyridine (HTFP) or conjugation products of 3-hydroxy-5-trifluoromethylpyridone (HPDO): each of the latter comprising about 1% of administered dose. Urine following administration of propenyl label consisted of many polar products, none of which was abundant. The majority of excreted radioactivity was obtained within the first 48 hrs after dosing, regardless of label position.

/SRP:/ 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/|/SRP:/ 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/|/SRP:/ 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 /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's 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/

2-(3-(2,6-Dichloro-4-((3,3-dichloro-2-propen-1-yl)oxy)phenoxy)propoxy)-5-(trifluoromethyl)pyridine

Pyridalyl Use and Manufacturing

Uses

For pyridalyl (USEPA/OPP Pesticide Code: 295149) 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./|Insecticide|For control of thrips and caterpillars in ornamentals.

Overture 35 WP Insecticide (Valent U.S.A. Corporation) 34-36% Pyridalyl|Suspension concentrate (= flowable concentrate); wettable powder.|Emulsifiable concentrate|S-1812 PPG Insecticide (Valent U.S.A. Corporation) 35% Pyridalyl

Adequate enforcement methodology (gas chromatography/nitrogen-phosphorus detector (GC/NPD) methods RM-38P-1-1, RM-38M-1, and RM-38M-1-1 for plant commodities; and RM-38P-2 and RM-38P-3-1 for livestock commodities) is available to enforce the tolerance expression.

Agrochemicals -> Insecticides

Computed Properties

Molecular Weight:491.1
XLogP3:7.1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:9
Exact Mass:490.965038
Monoisotopic Mass:488.967989
Topological Polar Surface Area:40.6
Heavy Atom Count:29
Complexity:511
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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