Acequinocyl

384.51

384.51

611-595-7

MQN165D1MB

DTXSID8034297

Pale yellowish flake

29153900

60.4

6.2

1.15 at 25 deg C

59.6°

504.0±50.0 °C at 760 mmHg

215.9±30.2 °C

1.530

Solubility in n-hexane 44 g/L, toluene 450 g/L, dichloromethane 620 g/L, acetone 220 g/L, methanol 7.8 g/L, and dimethylformamide 190 g/L.

0-6°C

1.27X10-8 mm Hg at 25 deg C

LD50 in rats (mg/kg): > 5000 orally, > 2000 dermally; in mice (mg/kg): > 5000 orally. LC50 (96hr) in carp, rainbow trout (mg/l): > 96.5, > 33 (Wakasa)

Faintly earthy

pH = 6.94

Henry's Law constant = 9.7X10-7 atm-cu m/mol at 25 °C /Estimated/

208.51 Ų [M-H]-

Hydroxyl radical reaction rate constant = 2.6X10-10 cu cm/molecule-sec at 25 °C /Estimated/|Ozone rate constant = 3.3X10-16 cu cm/molecule sec at 25 °C /Estimated/

Non-corrosive /End-use product/

UN 3077 9 / PGIII

3

50

61

QJ5375500

N

Hydrolysis DT50 19 days (pH 1.2, 37 deg C), 86 days (pH 4, 25 deg C), 52 hr (pH 7, 25 deg C), 76 min (pH 9, 25 deg C). Aqueous photolysis DT50 (pH 5) 6 days.

P260-P280-P308 + P311

H317-H370-H373-H410

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

Not compatible with alkaline products.

California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summaries. Available from: http://www.cdpr.ca.gov/docs/toxsums/toxsumlist.htm on Acequinocyl (57960-19-7) as of September 30, 2004

|Danger|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P260, P261, P264, P270, P272, P273, P280, P302+P352, P307+P311, P314, P321, P333+P313, P363, P391, P405, and P501|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|Aggregated GHS information provided by 212 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Approved respirator. Chemical-resistant gloves. Cover-alls over long-sleeved shirt and long pants. Protective eyewear and hat.|Use of Personal Protective Equipment (PPE) by applicators and other handlers, consisting of long-sleeved shirt and long pants, socks, shoes and chemical resistant gloves made of waterproof material.

Not highly flammable. /from table/

A restricted entry interval of 12 hours. The standard WPS drift restriction of not applying in any way that will contact workers or other persons, either directly or through drift, and the statement that only protected workers may be in the area during application.|Not for use in or around residential sites. For use only in commercial greenhouses and shadehouses. Restrictions for Use on Ornamental Crops Grown in Greenhouses: Do not apply through any type of irrigation system. Do not contaminate water, food or feed by storage or disposal. DO NOT contaminate water when disposing of equipment wash waters.

LD50 Rat oral >5000 mg/kg|LD50 Rat dermal >2000 mg/kg|LD50 Mouse oral >5000 mg/kg

Acequinocyl's production may result in its release to the environment through various waste streams; it's use as a greenhouse miticide for the treatment of ornamental plants grown in commercial greenhouses and shadehouses(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 56,000(SRC), determined from a log Kow of 6.2(2) and a regression-derived equation(3), indicates that acequinocyl is expected to be immobile in soil(SRC). Volatilization of acequinocyl from moist soil surfaces is expected to be slow(SRC) given an estimated Henry's Law constant of 9.7X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 1.27X10-8 mm Hg(2), and water solubility, 6.69X10-3 mg/L(2); adsorption to soil is expected to attenuate volatilization. Acequinocyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Observed half-lives of acequinocyl in sandy loam and silt soils were less than 2 days(2), indicating that biodegradation may be an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 56,000(SRC), determined from a log Kow of 6.2(2) and a regression-derived equation(3), indicates that acequinocyl is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected to be slow(3) based upon an estimated Henry's Law constant of 9.7X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 1.27X10-8 mm Hg(2), and water solubility, 6.69X10-3 mg/L(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 50 days and 550 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 4,800 years if adsorption is considered(4). According to a classification scheme(5), an estimated BCF of 33,000(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Acequinocyl is expected to undergo hydrolysis based on measured half-lives of 86 days at pH 4, 52 hours at pH 7, and 76 minutes at pH 9 (all at 25 °C)(7). The half-life for the aqueous photolysis of this substance was measured to be 6 days at pH 5(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acequinocyl, which has a vapor pressure of 1.27X10-8 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere.

Acequinocyl is expected to undergo hydrolysis based on measured half-lives of 86 days at pH 4, 52 hours at pH 7, and 76 minutes at pH 9 (all at 25 °C)(1). The half-life for the aqueous photolysis of this substance was measured to be 6 days at pH 5(1).

An estimated BCF of 33,000 was calculated for acequinocyl(SRC), using a log Kow of 6.2(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), provided the compound is not altered physically or chemically once released into the environment.

The Koc of acequinocyl is estimated as 56,000(SRC), using a log Kow of 6.2(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that acequinocyl is expected to be immobile in soil.

The Henry's Law constant for acequinocyl is estimated as 9.7X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 1.27X10-8 mm Hg(1), and water solubility, 6.69X10-3 mg/L(1). This Henry's Law constant indicates that acequinocyl is expected to volatilize slowly from water surfaces(2). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 50 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 550 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 4,800 years if adsorption is considered(3). Acequinocyl's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Acequinocyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Occupational exposure to acequinocyl may occur through inhalation and dermal contact with this compound at workplaces where acequinocyl is produced or used. The general population may be exposed to acequinocyl via dermal contact with ornamental plants that have been treated with this substance. (SRC)

Findings of red-brown to dark-red urine were noted in both sexes /of F344 rats after oral dosing/ at 800 and 1600 ppm. This may represent a metabolite of acequinocyl, which is a colored naphthoquinone similar to Vitamin K.|Small groups of CD rats were dosed orally with acequinocyl, labeled with 14C in the phenyl or dodecyl moieties, using 1% methyl cellulose as vehicle. Both label placements were involved in single low dose studies (10 mg/kg). High dose (500 mg/kg) and 14-day repeat-dose studies (10 mg/kg/day) were performed with phenyl-labeled acequinocyl only. Initial studies using CO2 traps found less than 0.2% of dose in exhaled air. Absorption was about 25-42%, based on bile duct cannulation studies, which found 20-33% of administered dose in bile, plus 5-9% in urine plus cage wash. Intact rats excreted most of the dose in feces, compared with less than 15% of label being found in urine. Clearance from the body was rapid, with reductions in most tissue levels at least 10-fold between 24 hr and 72 hr post-dosing. Parent compound was not detectable in urine, and was only a minor component (typically 1-2%) of fecal residues. Cleavage of the acetyl group of acequinocyl yielded 2-hydroxy-3-dodecyl-1,4-naphthalenedione (designated "R1") as a major fecal metabolite (12-36% of dose). Subsequent oxidation of the dodecyl chain yielded butanoic (AKM 14) and hexanoic (AKM 15) acids, the only measurable identified urinary metabolites. An apparent final product of epoxidation of R1 was AKM 18, [2- (1,2-dioxotetradecyl)-benzoic acid], which comprised 19-40% of label in feces. All four identified metabolites were found in bile and plasma in similar proportions. There were no remarkable differences in metabolite disposition due to gender, and no effect of pre-dosing for 2 weeks. The large dose slowed transit time and appreciably reduced absorption.|This study utilized 5 male CD rats, 3 of which were cannulated to obtain bile samples. Bile samples were evaluated for metabolite composition from 12 rats, including 3 rats/sex/treatment at low and high dose levels (10 and 500 mg/kg single dose treatments, respectively). The present study confirmed that the only two major urinary metabolites were AKM 14 and hexanoic AKM 15 ... The present study identified the major biliary metabolite as conjugate of 2-hydroxy-3-dodecyl-1,4-naphthalenedione, /the/ de-acetylated parent compound. The conjugation moiety is presumed to be glucuronic acid, based on the MW of the conjugated product.

The de-acetylated metabolite of acequinocyl, 2-hydroxy-3-dodecyl-1,4-naphthoquinone, strongly inhibits respiration in complex III of insect mitochondria. Compounds in this class have long been known to be complex III inhibitors in vertebrate systems. Structurally they resemble ubiquinone and they bind at the Qo center, probably competing with ubiquinone for this site. ... Their inhibitory potency depends on their lipophilicity and the optimal alkyl chain length is reached with the undecyl group.

/SRP:/ 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/|/SRP:/ 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/

3-dodecyl-1,4-dihydro-1,4-dioxo-2-naphthylacetate

Trade name: Piton|Kanemite|Suspension concentrate|Acequinocyl Technical is a powder composed of 96.8% Acequinocyl. This product is intended solely for manufacturing end-use products. Shuttle 15 SC Miticide is formulated as a flowable concentrate containing 1.25 pounds (lbs) of acequinocyl per gallon of product.

Preparation: R.F. Bellina, D.L. Fost, US 4082848 (1975, 1978 both to DuPont).

Agrochemicals -> Acaricides|Acaricides|Environmental transformation -> Pesticides (parent, predecessor)

Acequinocyl has known environmental transformation products that include AKM 18, AKM-13, AKM-14, AKM-15, CBAA, Phthalic acid, and R1.