Pyridaben
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Pyridaben
structure -
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CAS No:
96489-71-3
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Formula:
C19H25ClN2OS
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Chemical Name:
Pyridaben
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Synonyms:
3(2H)-Pyridazinone,4-chloro-2-(1,1-dimethylethyl)-5-[[[4-(1,1-dimethylethyl)phenyl]methyl]thio]-;4-Chloro-2-(1,1-dimethylethyl)-5-[[[4-(1,1-dimethylethyl)phenyl]methyl]thio]-3(2H)-pyridazinone;NCI 129;NC 129;Pyridaben;Sanmite;Nexter;Damanlin;BAS 300;2-tert-Butyl-5-(4-tert-butylbenzylthio)-4-chloropyridazin-3(2H)-one;Pyramite;GWN 1715
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CAS No:
Description
Beige Solid White to tan crystalline solid or powder.Faint vanilla odor. Commercial product is available as anemulsifiable concentrate or wettable powder.
Pyridaben is a pyridazinone, an organochlorine insecticide and an organochlorine acaricide. It has a role as a mitochondrial NADH:ubiquinone reductase inhibitor.
Pyridaben Basic Attributes
364.93300
364.93
405-700-3
2E4JBA5272
DTXSID5032573
Colorless crystals
2933399027
Characteristics
60.19000
5.24150
White solid
1.2 g/cm3 @ Temp: 20 °C
111-112 °C
429.9ºC at 760 mmHg
213.8ºC
1.564
In water, 0.012 mg/l @ 24 deg C
0-6ºC
1.18X10-6 mm Hg @ 20 deg C
LD50 in male, female rats, bobwhite quail, mallard ducks (mg/kg): 435, 358, >2250, >2500 orally (Hirata); LD50 in male, female rabbits (mg/kg): >2000, >2000 dermally (Hirata)
Odorless
Safety Information
II
6.1(a)
UN 3077
3
R23/25; R50/53
S36/37-S45-S60-S61
UR6149000
T; N
Stable at 50 deg C for 90 days; at pH 4, pH 7, & pH 9, in organic solvents; unstable to light.
P261-P273-P301 + P310-P311-P501
H301-H331-H410
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P273, P301+P310, P304+P340, P311, P321, P330, P391, P403+P233, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 94 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301+H331 (79.19%): Toxic if swallowed or if inhaled [Danger Acute toxicity, oral; acute toxicity, inhalation]|Aggregated GHS information provided by 197 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P301+P312, P304+P340, P309+P311, P311, P321, P330, P403+P233, P405, and P501|P260, P261, P264, P270, P271, P301+P310, P304+P340, P307+P311, P311, P312, P321, P330, P403+P233, P405, and P501
For handling activities, use a dust/mist filtering respirator... or a NIOSH approved respirator with a N, P, R, or HE prefilter. Wear long-sleeved shirt and long pants, socks and shoes and waterproof gloves. ...Wear goggles, face shield, or safety glasses. /Pyramite/
Wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet. Remove clothing immediately if pesticide gets inside. Remove PPE immediately after handling this product. Wash the outside of gloves before removing. As soon as possible, wash thoroughly and change into clean clothing. /Pyramite/
May be fatal if inhaled. Do not breathe dust or spray mist. ...Avoid contact with skin. ...Causes moderate eye irritation. Do not get in eyes or on clothing. /Pyramite/|Causes moderate eye injury. /Pyridaben K/
Toxicity
LD50 Rat (male) oral 1100 mg/kg|LD50 Rat (female) oral 570 mg/kg|LD50 Mouse (male) oral 424 mg/kg|LD50 Mouse (female) oral 383 mg/kg|For more Non-Human Toxicity Values (Complete) data for PYRIDABEN (6 total), please visit the HSDB record page.
/AQUATIC SPECIES/ Residual toxicities of avermectin b1 and pyridaben for 2- to 28-day exposure periods were assessed in laboratory and greenhouse trials for eight species of beneficial arthropods that are commercially produced for greenhouse pest management. In laboratory trials, Amblyseius degenerans (Berlese), Aphidius colemani (Viereck), Aphidoletes aphidimyza (Rondani), Dacnusa sibirica (Telenga), Encarsia formosa (Gahan), and Orius insidiosus (Say) showed high mortality (>85%) when exposed to 6-day residues of both acaricides. Lower toxicities were observed for pyridaben to the predatory mites Amblyseius cucumeris (Oudermans) and Phytoseiulus persimilis (Athias-Henroit), and for avermectin b1 to A. cucumeris after exposure to 6-day residues. In greenhouse trials, pyridaben showed significantly higher residual toxicity to all beneficial species than avermectin b1. Pyridaben had high residual toxicity (40-60% mortality) to E. formosa, A. colemani, A. aphidimyza, A. degenerans, and P. persimilis 6 days after treatment. Residual toxicity of pyridaben to D. sibirica, A. cucumeris, and O. insidiosus decreased to a low level (<15% mortality) after 6 days. Based on the results of the greenhouse trials, ...Pyridaben can ...be combined in Integrated Pest Management (IPM) programs with A. cucumeris, O. insidiosus, and D. sibirica after a 6-day residual period.
Pyridaben's production may result in its release to the environment through various waste streams; it's 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 >5000(5) indicates that pyridaben is expected to be immobile in soil(SRC). Volatilization of pyridaben from moist soil surfaces may occur(SRC) given an estimated Henry's Law constant of 4.7X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 1.18X10-6 mm Hg(4), and water solubility 0.012 mg/l(4). Pyridaben is not expected to volatilize from dry soil surfaces(SRC) based upon an experimental vapor pressure of 1.18X10-6 mm Hg(4). Pyridaben may undergo photolysis in surface soils and it has been reported that the photolytic half-life for the reaction is 12 days(5). Studies have shown that hydrolysis and biodegradation are not important environmental fate processes(5).|AQUATIC FATE: Based on a classification scheme(1), a Koc value of >5000(6) indicates that it is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(SRC) based upon an estimated Henry's Law constant of 4.7X10-5 atm-cu m/mole(2), derived from its vapor pressure, 1.18X10-6 mm Hg(3), and water solubility 0.012 mg/l(3). Using this Henry's Law constant and an estimation method(2), volatilization half-lives for a model river and model lake are 28 hours and 14 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 60 years(SRC) if adsorption is considered(5). According to a classification scheme(4), an estimated BCF of 7500(SRC), from its water solubility of 0.012 mg/l(3), and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). However, experimental data has shown that pyridaben has a low potential for bioconcentration in fish based on studies with rainbow trout and fathead minnow(6). It has been reported that photolysis is the main degradation route in water and that the photolytic half-life is 30 minutes(6). In an outdoor microcosm study, pyridaben was applied as an aqueous suspension at three concentrations (0.34, 3.4, 34.0 ug/l) to control tanks once in April and once in May. The dissipation half-life in microcosm water for the low, middle, and high treatment concentrations for both applications ranged from 11.8 to 28.5 hours(6). After both applications at 3.4 ug/l, pyridaben was not detected in sediment within 24 hours, whereas non-linear regression of residue data from the 34.0 ug/l tanks gave a dissipation half-life in sediment of approximately 9.8 days(6). Aerobic aquatic metabolism studies indicate that biodegradation and hydrolysis are not important routes for removal of pyridaben in aquatic systems(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pyridaben, which has an experimental vapor pressure of 1.18X10-6 mm Hg at 20 °C(3) is expected to exist in both the vapor and particulate phases in the ambient atmosphere(1). Vapor-phase pyridaben will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(2); the half-life for this reaction in air is estimated to be 9.4 hours(SRC). The rate constant for the vapor-phase reaction of pyridaben with ozone has been estimated as 1.7X10-16 cu cm/molecule-sec at 25 °C(SRC) which was derived using a structure estimation method(2). This corresponds to an atmospheric half- life of about 7 days(SRC) at an atmospheric concentration of 7X10+11 ozone molecules per cu cm. Pyridaben may also be susceptible to photolysis in the atmosphere since it has been shown to undergo aqueous photolysis(SRC). Particulate-phase pyridaben will be removed from the atmosphere by wet and dry deposition(2).
The rate constant for the vapor-phase reaction of pyridaben with photochemically-produced hydroxyl radicals has been estimated as 4.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 9.4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of pyridaben with ozone has been estimated as 1.6X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). Hydrolysis is not expected to be an important route for removal of pyridaben in aquatic systems(2). It has been reported that photolysis is the main degradation route in water and that the photolytic half-life is 30 minutes(2). The photolytic half-life in soil has been reported as 12 days(2). In an outdoor microcosm study, pyridaben was applied as an aqueous suspension at three concentrations (0.34, 3.4, 34.0 ug/l) to control tanks once in April and once in May. The dissipation half-life in microcosm water for the low, middle, and high treatment concentrations for both applications ranged from 11.8 to 28.5 hours(2). After both applications at 3.4 ug/l, pyridaben was not detected in sediment within 24 hours, whereas non-linear regression of residue data from the 34.0 ug/l tanks gave a dissipation half-life of approximately 9.8 days(2). Studies indicate that hydrolysis of pyridaben is not an important environmental fate(2).
An estimated BCF of 7500(SRC) was calculated for pyridaben, using an experimental water solubility of 0.012 mg/l(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(SRC). However, experimental data has shown that pyridaben has a low potential for biocentration in fish based on studies with rainbow trout and fathead minnow(4).
The Koc value for pyridaben is >5000(1) and according to a classification scheme(2), this Koc value suggests that pyridaben is expected to be immobile in soil.
The Henry's Law constant for pyridaben is estimated as 4.7X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 1.18X10-6 mm Hg(1), and water solubility, 0.012 mg/l(1). This estimated Henry's Law constant indicates that pyridaben may volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 28 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 14 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 60 years(SRC) if adsorption is considered(4). Pyridaben's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Pyridaben is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 1.18X10-6 mm Hg(2).
Occupational exposure to pyridaben may occur through inhalation and dermal contact with this compound at workplaces where pyridaben is produced or used. (SRC)
Drug Information
In a... rat metabolism study by the oral route, pyridaben was mainly eliminated in feces where 80-97% of the administered dose was excreted regardless of dose or site of label (pyridazinone or benzyl ring). Nearly 20% of the excreted residue in the feces was unmetabolized parent compound and there was some evidence of glucuronide conjugate(s) in the bile. The plasma levels following a single low oral dose (3 mg/kg) peaked at 2-3 hours while peak levels at the high dose (30 mg/kg) were at approximately 24 hours post-dose due, at least in part, to enterohepatic circulation where nearly 22-30% of an administered radioactive dose is excreted in bile within a period of 24 hours. Residual radioactivity was at or near background levels for most tissues by 72-168 hours. Generally, there seemed to be increased distribution to fat over time and, compared to other tissues, fat seemed to have relatively more residual radioactivity.
In a... rat metabolism study by the oral route, pyridaben was mainly eliminated in feces where 80-97% of the administered dose was excreted regardless of dose or site of label (pyridazinone or benzyl ring). Nearly 20% of the excreted residue in the feces was unmetabolized parent compound and there was some evidence of glucuronide conjugate(s) in the bile. The plasma levels following a single low oral dose (3 mg/kg) peaked at 2-3 hours while peak levels at the high dose (30 mg/kg) were at approximately 24 hours post-dose due, at least in part, to enterohepatic circulation where nearly 22-30% of an administered radioactive dose is excreted in bile within a period of 24 hours. Residual radioactivity was at or near background levels for most tissues by 72-168 hours. Generally, there seemed to be increased distribution to fat over time and, compared to other tissues, fat seemed to have relatively more residual radioactivity.
... It is ... proposed that NADH: ubiquinone oxidoreductase inhibitors /including pyridaben/ block multiple and possibly reactive oxygen species-modulated pathways which regulate ornithine decarboxylase activity.
Basic treatment: Establish a patent airway. 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 normal saline 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 ... . /Poison 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 respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/|If inhaled: Remove victim to fresh air. Apply artificial respiration if indicated. If swallowed: Call a physician or Poison Control Center. Drink 1 or 2 glasses of water and induce vomiting by touching back of throat with finger. Do not induce vomiting or give anything by mouth to an unconscious person. If in eyes: Flush eyes with plenty of water. Call a physician if irritation persists. If on skin: Wash with plenty of soap and water. Get medical attention if irritation persists. /Pyridaben K/
2-tert-butyl-5-(4-tert-butyl-benzylthio)-4-chloropyridazin-3(2H)-one
Pyridaben Use and Manufacturing
JP Kokai 85 4173; M. Taniguchi et al, US 4877787 (1985, 1989, both to Nissan)
It is used to control various mites on fruit trees, cotton, wheat, peanuts, vegetables and other crops; it is a broad-spectrum, contact-killing acaricide insecticide, which is used to control mites on cotton, citrus, fruit trees and other economic crops. Production method Preparation method one
USEPA/OPP Pesticide Code 129105; Trade Names: BASF 300 75WP, NCI 129, Nester, Sanmite, BASF 300 75 WP, BASF 300.|Emulsifiable concentrate, wettable powder, suspension concentrate|BASF Pyridaben Manufacturing Use Product (99.4% Pyridaben)|Pyramite (60% Pyridaben)|For more Formulations/Preparations (Complete) data for PYRIDABEN (8 total), please visit the HSDB record page.
Rapid knock-down and long residual activity. Has activity against all developing stages, especially against the larval and nymph stages.
Pesticide or Metabolite (M) Common Name: Pyridaben; Commodity: Almond nuts; Method Source: BASF; Method ID: D9312; Method Date: 4/94; Instrument: GC/ECD; Estimated LOQ (ppm): 0.025. /From table/|Pesticide or Metabolite (M) Common Name: Pyridaben; Commodity: Apples; Method Source: BASF; Method ID: D9312; Method Date: April 94; Instrument: GC/ECD; Estimated LOQ (ppm): 0.003. /From table/|Pesticide or Metabolite (M) Common Name: Pyridaben; Commodity: Liver; Method Source: BASF; Method ID: D9405; Method Date: 94; Instrument: GC/ECD; Estimated LOQ (ppm): 0.005. /From table/|Pesticide or Metabolite (M) Common Name: Pyridaben; Commodity: Milk; Method Source: BASF; Method ID: D9405; Method Date: 94; Instrument: GC/ECD; Estimated LOQ (ppm): 0.003. /From table/|Pesticide or Metabolite (M) Common Name: Pyridaben; Commodity: Oranges; Method Source: BASF; Method ID: 93102; Method Date: 4/7/94; Instrument: GC/ECD; Estimated LOQ (ppm): 0.01. /From table/
Agrochemicals -> Acaricides, Insecticides
Computed Properties
Molecular Weight:364.9
XLogP3:5.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:364.1376123
Monoisotopic Mass:364.1376123
Topological Polar Surface Area:58
Heavy Atom Count:24
Complexity:535
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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