57960-19-7CCCCCCCCCCCCC1=C(OC(C)=O)C(=O)c2ccccc2C1=OQDRXWCAVUNHOGA-UHFFFAOYSA-NAcequinocyl is an acetate ester consisting of 1,4-naphthoquinone bearing acetoxy and dodecyl substituents at positions 2 and 3 respectively. It has a role as an acaricide and a mitochondrial cytochrome-bc1 complex inhibitor. It is a member of 1,4-naphthoquinones and an acetate ester.
57960-19-7Pesticides
Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Approved
Pesticides -> Other Insecticides
Acaricides
Pesticide
1.15 at 25 °C
Relative density = 1.04 /End-use product/
In water, 6.69X10-3 mg/L at 20 °C
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.
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Danger
H317: May cause an allergic skin reaction [Warning Sensitization, Skin]
P260, P261, P264, P270, P272, P273, P280, P302+P352, P308+P316, P319, P321, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Danger
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P260, P261, P264, P270, P272, P273, P280, P302+P352, P308+P316, P319, P321, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Regulation (EC) No 396/2005 (amended)
Acequinocyl is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
Dossier complete 03/636/EC, Reg. (EU) 2018/155, Reg. (EU) 2020/2007, Reg. (EU) 2024/2221, Reg. (EU) No 496/2014, Reg. (EU) No 540/2011
Tolerances for combined residues of the insecticide acequinocyl, 2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione, and its metabolite, 2-dodecyl-3-hydroxy-1,4-naphthoquinone, expressed as acequinocyl equivalents in or on the following commodities: almond; almond, hulls; apple, wet pomace; cattle, fat; cattle, liver; citrus, oil; fruit, citrus, group 10; fruit, pome, group 11; goat, fat; goat, liver; horse, fat; horse, liver; pistachio; sheep, fat; sheep, liver; and strawberry.
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.
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.
Wird geladen…
DTXSID8034297CHEMBL1869353CHEBI:385920.00000001 [mmHg]
1.27X10-8 mm Hg at 25 °C
Skin Sens. 1 (100%)
Skin sensitisation - category 1
STOT SE 1
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.
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.
Tolerances for combined residues of the insecticide acequinocyl, 2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione, and its metabolite, 2-dodecyl-3-hydroxy-1,4-naphthoquinone, expressed as acequinocyl equivalents in or on the following commodities: almond 0.02 ppm; almond, hulls 2.0 ppm; apple, wet pomace 1.0 ppm; cattle, fat 0.02 ppm; cattle, liver 0.02 ppm; citrus, oil 30 ppm; fruit, citrus, group 10, 0.20 ppm; fruit, pome, group 11, 0.40 ppm; goat, fat 0.02 ppm; goat, liver 0.02 ppm; horse, fat 0.02 ppm; horse, liver 0.02 ppm; pistachio 0.02 ppm; sheep, fat 0.02 ppm; sheep, liver 0.02 ppm; and strawberry 0.40 ppm.
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.
LC50 Carp >96.5 mg/L/96 hr /Conditions of bioassay not specified in source examined/
LC50 Rainbow trout >33 mg/L/96 hr /Conditions of bioassay not specified in source examined/
LD50 Anas platyrhynchos (Mallard duck) oral 2000 mg/kg
LC50 Anas platyrhynchos (Mallard duck) dietary >5000 ppm (5 days)
For more Ecotoxicity Values (Complete) data for ACEQUINOCYL (9 total), please visit the HSDB record page.
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.
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.
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).
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 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).
/LABORATORY ANIMALS: Acute Exposure/ Very mild skin and eye irritant (rabbits). Not a skin sensitiser (guinea pigs).
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Acequinocyl technical (purity=96.5%) was admixed to the feed and fed to 10 F344/DuCrj (Fischer) rats per sex per dose at dose levels of 0 (basal diet only), 100, 400, 1600, or 3200 ppm (0, 7.57, 30.4, 120, 253 mg/kg/day, respectively for males and 0, 8.27, 32.2, 129, 286 mg/kg/day, respectively for females) for 13 consecutive weeks. All animals at 3200 ppm died during the first 3 weeks of the study; no other mortalities occurred. Treatment-related reddish urine was observed in both sexes at 1600 ppm from Week 2 through Week 13. Hematology revealed a treatment-related increase in mean white blood cells and platelets in males at 1600 ppm with a treatment-related increase in mean prothrombin time and activated partial thromboplastin time in both males and females at 1600 ppm. Urinalysis revealed treatment-related red-brown urine in all animals of both sexes at 1600 which is consistent with the increased number of animals with bilirubin in their urine. Treatment-related yellow-brown urine in all animals of both sexes at 400 ppm suggesting the presence of the metabolite of the test material. Macroscopic examination on the surviving animals revealed an enlarged eye in 2 females at 1600 ppm. Microscopic examination on the surviving animals revealed no treatment related abnormalities. Macroscopic and microscopic examinations of the mortalities (including animals in moribund condition) revealed hemorrhaging of muscle and other organs and wasting of the whole body at 1600 and 3200 ppm dose levels. Possible adverse effect: inhibition of the coagulation system. /Tecnical product/
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Acequinocyl technical (purity = 97.1%) was made into a paste with 1% methylcellulose (w/v) and applied to the clipped dorsal skin of 10 Crl:(IGS)CD BR rats per sex per dose at dose levels of 0 (vehicle only), 40, 200, or 1000 mg/kg/day (plus an additional 10 animals per sex per dose at 0 and 1000 mg/kg/day to assess recovery for 2 weeks) for 6 hours per day 7 days a week for at least 28 days using a semi-occlusive dressing. No treatment related mortalities occurred. Red staining on the back of all animals at 40, 200, and 1000 mg/kg/day was observed in the morning only, from Day 2 through Day 13; the number of animals exhibiting this sign decreased in a dose-related manner after Day 13. The biological significance of this sign is unknown at this time. Hematological investigations revealed treatment-related increases in mean prothrombin time (in males only), activated partial thromboplastin time (in males and females), and fibrinogen (in males only) levels at 1000 mg/kg/day. Macroscopic and microscopic examinations revealed no treatment-related abnormalities. No adverse effects. NOEL (M/F, systemic) = 200 mg/kg/day based on blood clotting parameters. NOEL (M/F, skin) = 1000 mg/kg/day based on no treatment-related effects at the highest dose tested. /Tecnical product/
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).
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)
Tolerances for combined residues of the insecticide acequinocyl, 2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione, and its metabolite, 2-dodecyl-3-hydroxy-1,4-naphthoquinone, expressed as acequinocyl equivalents in or on the following commodities: almond; almond, hulls; apple, wet pomace; cattle, fat; cattle, liver; citrus, oil; fruit, citrus, group 10; fruit, pome, group 11; goat, fat; goat, liver; horse, fat; horse, liver; pistachio; sheep, fat; sheep, liver; and strawberry.
Used as an acaricide and insecticide; [HSDB] Registered for ornamental plants grown in greenhouses and shadehouses to control mites; [Reference #1]
Farming (Pesticides) [Category: Industry]
For acequinocyl (USEPA/OPP Pesticide Code: 006329) 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./
Acaracide
Insecticide; controls Aculops,Panonychus, Polyphagatarsonemeus, and Tetranychus in apple, cherry, citrus, melon, pear, peach, cucumber, ornamentals, and vegetables.
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.
Acaricides
Environmental transformation -> Pesticides (parent, predecessor)
VerwendenAcaricide.
DefinitionChEBI: An acetate ester consisting of 1,4-naphthoquinone bearing acetoxy and dodecyl substituents at positions 2 and 3 respectively.
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Diets containing 0, 50, 200, 800, and 1600 ppm acequinocyl (97.1%) /were fed to F344 rats/. Reported mean test substance intakes were 2.25, 9.02, 36.4, and 74.0 mg/kg/day in males and 2.92, 11.6, 46.3, and 93.6 mg/kg/day in females. Fifty F344 rats/sex/group were assigned to the lifetime (2-yr) study. An additional 10/sex/group constituted interim sacrifice groups, terminated at weeks 26, 52, and 78. The latter rats were used for clinical chemistry, hematology, and urinalysis. Interim rats were all examined grossly, however histopathology of interim groups was limited to the 1-yr sacrifice rats. NOEL = 50 ppm (dose-related increases in "hypertrophy of the eyeball" in 200 ppm males). "Hypertrophy of the eyeball" and "corneal abnormality" were common findings in 800 and 1600 ppm males. "Hypertrophy of the eyeball" was a treatment response in 1600 ppm females. ...Definitive treatment effects were limited to 1600 ppm males, such as body weight decrements and hematology changes, which were generally only remarkable during the first year [increased platelet counts, increased prothrombin time, and increased activated partial thromboplastin time (APTT)]. Ophthalmology was only performed at 2-yr termination, which was beyond the optimal time to distinguish ocular treatment effects. Nevertheless, high dose rats had small increases of cases in which the ocular fundus could not be visualized. /Technical product/
For more Non-Human Toxicity Excerpts (Complete) data for ACEQUINOCYL (14 total), please visit the HSDB record page.