An official website of the United States government

Acequinocyl

PubChem CID
93315
Structure
Acequinocyl_small.png
Acequinocyl_3D_Structure.png
Molecular Formula
Synonyms
  • Acequinocyl
  • 57960-19-7
  • Acequinocyl [ISO]
  • Acequincyl
  • 2-(Acetyloxy)-3-dodecyl-1,4-naphthalenedione
Molecular Weight
384.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-02-01
Description
Acequinocyl 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 a mitochondrial cytochrome-bc1 complex inhibitor and an acaricide. It is an acetate ester and a member of 1,4-naphthoquinones.
Acequinocyl has been reported in Apis cerana with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Acequinocyl.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3-dodecyl-1,4-dioxonaphthalen-2-yl) acetate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C24H32O4/c1-3-4-5-6-7-8-9-10-11-12-17-21-22(26)19-15-13-14-16-20(19)23(27)24(21)28-18(2)25/h13-16H,3-12,17H2,1-2H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

QDRXWCAVUNHOGA-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCCCCCCCCCCCC1=C(C(=O)C2=CC=CC=C2C1=O)OC(=O)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C24H32O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

191490-28-5

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 KEGG ID

2.3.9 Metabolomics Workbench ID

2.3.10 Nikkaji Number

2.3.11 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

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

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
384.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
7.6
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
13
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
384.23005950 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
384.23005950 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
60.4 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
28
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
575
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Yellowish solid; [Merck Index]

3.2.2 Color / Form

Pale yellowish flake
Crop Protection Handbook 2004. (Formerly Farm and Chemicals Handbook) Willoughby, OH: Meister Publishing Co., 2004., p. C 37

3.2.3 Odor

Faintly earthy
US EPA; EPA Fact Sheets on New Active Ingredients. Acequinocyl. Available from, as of Sept 22, 2004: https://www.epa.gov/opprd001/factsheets/

3.2.4 Melting Point

59.6 °C
British Crop Protection Council. The e-Pesticide Manual. 13th ed. Surrey, UK. Version 3.0 Acequinocyl Record no. 3 (2003)

3.2.5 Solubility

In water, 6.69X10-3 mg/L at 20 °C
US EPA; EPA Fact Sheets on New Active Ingredients. Acequinocyl. Available from, as of Sept 22, 2004: https://www.epa.gov/opprd001/factsheets/
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.
British Crop Protection Council. The e-Pesticide Manual. 13th ed. Version 3.0 Acequinocyl Record no. 3 (2003)

3.2.6 Density

1.15 at 25 °C
British Crop Protection Council. The e-Pesticide Manual. 13th ed. Surrey, UK. Version 3.0 Acequinocyl Record no. 3 (2003)
Relative density = 1.04 /End-use product/
US EPA; EPA Fact Sheets on New Active Ingredients. Acequinocyl. Available from, as of Sept 22, 2004: https://www.epa.gov/opprd001/factsheets/

3.2.7 Vapor Pressure

0.00000001 [mmHg]
1.27X10-8 mm Hg at 25 °C
US EPA; EPA Fact Sheets on New Active Ingredients. Acequinocyl. Available from, as of Sept 22, 2004: https://www.epa.gov/opprd001/factsheets/

3.2.8 LogP

log Kow = 6.2
US EPA; EPA Fact Sheets on New Active Ingredients. Acequinocyl. Available from, as of Sept 22, 2004: https://www.epa.gov/opprd001/factsheets/

3.2.9 Henry's Law Constant

Henry's Law constant = 9.7X10-7 atm-cu m/mol at 25 °C /Estimated/
US EPA; Estimation Program Interface (EPI) Suite. Ver.3.11. June 10, 2003. Available from, as of Sept 22, 2004: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm

3.2.10 Stability / Shelf Life

Hydrolysis DT50 19 days (pH 1.2, 37 °C), 86 days (pH 4, 25 °C), 52 hr (pH 7, 25 °C), 76 min (pH 9, 25 °C). Aqueous photolysis DT50 (pH 5) 6 days.
Tomlin CDS, ed. Acequinocyl (57960-19-7). In: The e-Pesticide Manual, Version 2.2 (2002). Surrey UK, British Crop Protection Council.

3.2.11 Viscosity

405.95 cS at 20 °C; 217.23 cS at 40 °C /End-use product/
US EPA; EPA Fact Sheets on New Active Ingredients. Acequinocyl. Available from, as of Sept 22, 2004: https://www.epa.gov/opprd001/factsheets/

3.2.12 Corrosivity

Non-corrosive /End-use product/
US EPA; EPA Fact Sheets on New Active Ingredients. Acequinocyl. Available from, as of Sept 22, 2004: https://www.epa.gov/opprd001/factsheets/

3.2.13 pH

pH = 6.94
US EPA; EPA Fact Sheets on New Active Ingredients. Acequinocyl. Available from, as of Sept 22, 2004: https://www.epa.gov/opprd001/factsheets/

3.2.14 Collision Cross Section

208.51 Ų [M-H]-
S61 | UJICCSLIB | Collision Cross Section (CCS) Library from UJI | DOI:10.5281/zenodo.3549476

3.2.15 Other Experimental Properties

Hydroxyl radical reaction rate constant = 2.6X10-10 cu cm/molecule-sec at 25 °C /Estimated/
US EPA; Estimation Program Interface (EPI) Suite. Ver.3.11. June 10, 2003. Available from, as of Sept 22, 2004: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
Ozone rate constant = 3.3X10-16 cu cm/molecule sec at 25 °C /Estimated/
US EPA; Estimation Program Interface (EPI) Suite. Ver.3.11. June 10, 2003. Available from, as of Sept 22, 2004: https://www.epa.gov/oppt/exposure/pubs/episuitedl.htm

3.3 Chemical Classes

3.3.1 Pesticides

Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Approved
Pesticides -> Other Insecticides
Environmental transformation -> Pesticides (parent, predecessor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759
Pesticide
S120 | DUSTCT2024 | Substances from Second NORMAN Collaborative Dust Trial | DOI:10.5281/zenodo.13835254
Acaricides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688
Pesticide (Acequinocyl) -> USDA PDB

5 Chemical Vendors

6 Agrochemical Information

6.1 Agrochemical Category

Miticide
Pesticide active substances
Acaricides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

6.2 Agrochemical Transformations

Acequinocyl has known environmental transformation products that include AKM-13, AKM-14, AKM-15, R1, AKM 18, Phthalic acid, and CBAA.
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759

6.3 EU Pesticides Data

Active Substance
acequinocyl
Status
Approved [Reg. (EC) No 1107/2009]
Date
Approval: 01/09/2014 Expiration: 15/11/2026
Legislation
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
ADI
0.023 mg/kg bw/day [Reg. (EU) No 496/2014]
ARfD
0.08 mg/kg bw [Reg. (EU) No 496/2014]
AOEL
0.014 mg/kg bw/day [Reg. (EU) No 496/2014]

6.4 USDA Pesticide Data Program

7 Pharmacology and Biochemistry

7.1 Metabolism / Metabolites

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

7.2 Mechanism of Action

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.
Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 2, 2nd ed. 2001. Academic Press, San Diego, California., p. 1208

7.3 Transformations

8 Use and Manufacturing

8.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Used as an acaricide and insecticide; [HSDB] Registered for ornamental plants grown in greenhouses and shadehouses to control mites; [Reference #1]
Industrial Processes with risk of exposure
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./
U.S. Environmental Protection Agency/Office of Pesticide Program's Chemical Ingredients Database on Acequinocyl (57960-19-7). Available from, as of November 1, 2004: https://npirspublic.ceris.purdue.edu/ppis/
Acaracide
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 8
Insecticide; controls Aculops,Panonychus, Polyphagatarsonemeus, and Tetranychus in apple, cherry, citrus, melon, pear, peach, cucumber, ornamentals, and vegetables.
Crop Protection Handbook 2004. (Formerly Farm and Chemicals Handbook) Willoughby, OH: Meister Publishing Co., 2004., p. C-37

8.1.1 Use Classification

Environmental transformation -> Pesticides (parent, predecessor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759
Acaricides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

8.2 Formulations / Preparations

Trade name: Piton
Crop Protection Handbook 2004. (Formerly Farm and Chemicals Handbook) Willoughby, OH: Meister Publishing Co., 2004., p. C-37
Kanemite
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 8
Suspension concentrate
Crop Protection Handbook 2004. (Formerly Farm and Chemicals Handbook) Willoughby, OH: Meister Publishing Co., 2004., p. C-37
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.
USEPA/Office of Pesticide Programs; Pesticide Fact Sheet- Acequinocyl (September 2003). Available from, as of November 16, 2004: https://www.epa.gov/opprd001/factsheets/

8.3 General Manufacturing Information

Preparation: R.F. Bellina, D.L. Fost, US 4082848 (1975, 1978 both to DuPont).
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 8

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

1 of 3
View All
Pictogram(s)
Irritant
Health Hazard
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H370 (100%): Causes damage to organs [Danger Specific target organ toxicity, single exposure]

H373 (100%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

H400 (81.2%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P260, P261, P264, P270, P272, P273, P280, P302+P352, P308+P316, P319, P321, P333+P317, P362+P364, P391, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 85 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Skin Sens. 1 (100%)

STOT SE 1 (100%)

STOT RE 2 (100%)

Aquatic Acute 1 (81.2%)

Aquatic Chronic 1 (100%)

Skin sensitisation - category 1

Specific target organ toxicity (single exposure) - category 1

Specific target organ toxicity (repeated exposure) - category 2

Hazardous to the aquatic environment (acute) - category 1

Hazardous to the aquatic environment (chronic) - category 1

9.1.3 Hazards Summary

Causes liver injury, increased clotting factor times, and spastic paralysis in high-dose animal studies; [RTECS] In animals, causes mild skin irritation but not sensitization; [HSDB]

9.1.4 Fire Potential

Not highly flammable. /from table/
USEPA/Office of Pesticide Programs; Pesticide Fact Sheet- Acequinocyl (September 2003). Available from, as of November 16, 2004: https://www.epa.gov/opprd001/factsheets/

9.2 Accidental Release Measures

9.2.1 Disposal Methods

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.

9.2.2 Preventive Measures

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.
USEPA/Office of Pesticide Programs; Pesticide Fact Sheet- Acequinocyl (September 2003). Available from, as of November 16, 2004: https://www.epa.gov/opprd001/factsheets/
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.
USEPA/Office of Pesticide Programs; Pesticide Fact Sheet- Acequinocyl (September 2003). Available from, as of November 16, 2004: https://www.epa.gov/opprd001/factsheets/

9.3 Handling and Storage

9.3.1 Storage Conditions

Store in dark, fully ventilated place at room temperature (do not exceed 40 °C).
Crop Protection Handbook 2004. (Formerly Farm and Chemicals Handbook) Willoughby, OH: Meister Publishing Co., 2004., p. C-37

9.4 Exposure Control and Personal Protection

9.4.1 Allowable Tolerances

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.
40 CFR 180.599(a); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of November 1, 2004: https://www.ecfr.gov

9.4.2 Personal Protective Equipment (PPE)

Approved respirator. Chemical-resistant gloves. Cover-alls over long-sleeved shirt and long pants. Protective eyewear and hat.
Crop Protection Handbook 2004. (Formerly Farm and Chemicals Handbook) Willoughby, OH: Meister Publishing Co., 2004., p. C-37
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.
USEPA/Office of Pesticide Programs; Pesticide Fact Sheet- Acequinocyl (September 2003). Available from, as of November 16, 2004: https://www.epa.gov/opprd001/factsheets/

9.5 Stability and Reactivity

9.5.1 Hazardous Reactivities and Incompatibilities

Not compatible with alkaline products.
Tomlin CDS, ed. Acequinocyl (57960-19-7). In: The e-Pesticide Manual, Version 2.2 (2002). Surrey UK, British Crop Protection Council.

9.6 Regulatory Information

Status Regulation (EC)
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

9.6.1 FIFRA Requirements

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.
40 CFR 180.599(a); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of November 1, 2004: https://www.ecfr.gov

9.7 Other Safety Information

9.7.1 Special Reports

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

10 Toxicity

10.1 Toxicological Information

10.1.1 RAIS Toxicity Values

Oral Acute Reference Dose (RfDoa)(mg/kg-day)
0.073
Oral Acute Reference Dose Reference
OPP
Oral Chronic Reference Dose (RfDoc) (mg/kg-day)
0.027
Oral Chronic Reference Dose Reference
OPP

10.1.2 EPA Human Health Benchmarks for Pesticides

Chemical Substance
Acute or One Day PAD (RfD) [mg/kg/day]
0.073
Acute or One Day HHBPs [ppb]
490
Acute HHBP Sensitive Lifestage/Population
Children
Chronic or One Day PAD (RfD) [mg/kg/day]
0.027
Chronic or One Day HHBPs [ppb]
160
Chronic HHBP Sensitive Lifestage/Population
General Population

10.1.3 Evidence for Carcinogenicity

Cancer Classification: Not Likely to be Carcinogenic to Humans
USEPA Office of Pesticide Programs, Health Effects Division, Science Information Management Branch: "Chemicals Evaluated for Carcinogenic Potential" (April 2006)

10.1.4 Adverse Effects

Neurotoxin - Other CNS neurotoxin

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

10.1.5 Acute Effects

10.1.6 Antidote and Emergency Treatment

/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/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 139
/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/
Bronstein, A.C., P.L. Currance; Emergency Care for Hazardous Materials Exposure. 2nd ed. St. Louis, MO. Mosby Lifeline. 1994., p. 139

10.1.7 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ Very mild skin and eye irritant (rabbits). Not a skin sensitiser (guinea pigs).
Tomlin CDS, ed. Acequinocyl (57960-19-7). In: The e-Pesticide Manual, Version 2.2 (2002). Surrey UK, British Crop Protection Council.
/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/
California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summaries. Available from: https://www.cdpr.ca.gov/docs/toxsums/toxsumlist.htm on Acequinocyl (57960-19-7) as of September 30, 2004
/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/
California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summaries. Available from: https://www.cdpr.ca.gov/docs/toxsums/toxsumlist.htm on Acequinocyl (57960-19-7) as of September 30, 2004
/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/
California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summaries. Available from: https://www.cdpr.ca.gov/docs/toxsums/toxsumlist.htm on Acequinocyl (57960-19-7) as of September 30, 2004
For more Non-Human Toxicity Excerpts (Complete) data for ACEQUINOCYL (14 total), please visit the HSDB record page.

10.1.8 Non-Human Toxicity Values

LD50 Rat oral >5000 mg/kg
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 8
LD50 Rat dermal >2000 mg/kg
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 8
LD50 Mouse oral >5000 mg/kg
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 8

10.2 Ecological Information

10.2.1 EPA Ecotoxicity

Pesticide Ecotoxicity Data from EPA

10.2.2 Ecotoxicity Values

LC50 Carp >96.5 mg/L/96 hr /Conditions of bioassay not specified in source examined/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 8
LC50 Rainbow trout >33 mg/L/96 hr /Conditions of bioassay not specified in source examined/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 8
LD50 Anas platyrhynchos (Mallard duck) oral 2000 mg/kg
Tomlin CDS, ed. Acequinocyl (57960-19-7). In: The e-Pesticide Manual, Version 2.2 (2002). Surrey UK, British Crop Protection Council.
LC50 Anas platyrhynchos (Mallard duck) dietary >5000 ppm (5 days)
Tomlin CDS, ed. Acequinocyl (57960-19-7). In: The e-Pesticide Manual, Version 2.2 (2002). Surrey UK, British Crop Protection Council.
For more Ecotoxicity Values (Complete) data for ACEQUINOCYL (9 total), please visit the HSDB record page.

10.2.3 Environmental Fate / Exposure Summary

Acequinocyl's production may result in its release to the environment through various waste streams; it's use as a greenhouse miticide will result in its direct release to the environment. If released to air, a vapor pressure of 1.27X10-8 mm Hg at 25 °C indicates acequinocyl will exist solely in the particulate phase in the ambient atmosphere. Particulate-phase acequinocyl will be removed from the atmosphere by wet and dry deposition. If released to soil, acequinocyl is expected to have no mobility based upon an estimated Koc of 56,000. Observed half-lives of acequinocyl in sandy loam and silt soils were less than 2 days, indicating that biodegradation may be an important environmental fate process in soil. Volatilization from moist soil surfaces is expected to be slow based upon an estimated Henry's Law constant of 9.7X10-7 atm-cu m/mole; adsorption to soil is expected to attenuate volatilization. Acequinocyl is not expected to volatilize from dry soil surfaces. If released into water, acequinocyl is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is expected to be slow based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 50 days and 550 days, respectively. 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. An estimated BCF of 33,000 suggests the potential for bioconcentration in aquatic organisms is very high. 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). The half-life for the aqueous photolysis of this substance was measured to be 6 days at pH 5. 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)

10.2.4 Artificial Pollution Sources

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).
(1) US EPA; EPA Fact Sheets on New Active Ingredients. Acequinocyl. Available at https://www.epa.gov/opprd001/factsheets/ as of Sept 22, 2004.

10.2.5 Environmental Fate

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).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) US EPA; EPA Fact Sheets on New Active Ingredients. Acequinocyl. Available at https://www.epa.gov/opprd001/factsheets/ as of Sept 22, 2004.
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990)
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).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) US EPA; EPA Fact Sheets on New Active Ingredients. Acequinocyl. Available at https://www.epa.gov/opprd001/factsheets/ as of Sept 22, 2004.
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9, 15-1 to 15-29 (1990)
(4) US EPA; EXAMS II Computer Simulation (1987)
(5) Franke C et al; Chemosphere 29: 1501-14 (1994)
(6) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(7) British Crop Protection Council. The e-Pesticide Manual. 13th ed. Version 3.0 Acequinocyl Record no. 3 (2003)
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.
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) US EPA; Fact Sheets on New Active Ingredients. Acequinocyl. Available at https://www.epa.gov/opprd001/factsheets/ as of Sept 22, 2004.
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)

10.2.6 Environmental Biodegradation

AEROBIC: Observed half-lives of acequinocyl in sandy loam and silt soils were less than 2 days(1). Deacetylated acequinocyl was reported as a major metabolite(1).
(1) US EPA; Fact Sheets on New Active Ingredients. Acequinocyl. Available at https://www.epa.gov/opprd001/factsheets/ as of Sept 22, 2004.

10.2.7 Environmental Abiotic Degradation

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).
(1) British Crop Protection Council. The e-Pesticide Manual. 13th ed. Version 3.0 Acequinocyl Record no. 3 (2003)

10.2.8 Environmental Bioconcentration

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.
(1) US EPA; EPA Fact Sheets on New Active Ingredients. Acequinocyl. Available at https://www.epa.gov/opprd001/factsheets/ as of Sept 22, 2004.
(2) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

10.2.9 Soil Adsorption / Mobility

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.
(1) US EPA; EPA Fact Sheets on New Active Ingredients. Acequinocyl. Available at https://www.epa.gov/opprd001/factsheets/ as of Sept 22, 2004.
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990)
(3) Swann RL et al; Res Rev 85: 17-28 (1983)

10.2.10 Volatilization from Water / 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).
(1) US EPA; EPA Fact Sheets on New Active Ingredients. Acequinocyl. Available at https://www.epa.gov/opprd001/factsheets/ as of Sept 22, 2004.
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(3) US EPA; EXAMS II Computer Simulation (1987)

10.2.11 Probable Routes of Human Exposure

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)

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Chemical Co-Occurrences in Literature

11.5 Chemical-Gene Co-Occurrences in Literature

11.6 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

14 Biological Test Results

14.1 BioAssay Results

15 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 KEGG: Pesticides

16.4 ChemIDplus

16.5 UN GHS Classification

16.6 EPA CPDat Classification

16.7 NORMAN Suspect List Exchange Classification

16.8 EPA DSSTox Classification

16.9 LOTUS Tree

16.10 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. EPA Safe Drinking Water Act (SDWA)
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    acequinocyl (ISO) 3-dodecyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl acetate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.110.102
    acequinocyl (ISO) 3-dodecyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl acetate (EC: 611-595-7)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/18932
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Hazardous Substances Data Bank (HSDB)
  8. Risk Assessment Information System (RAIS)
    LICENSE
    This work has been sponsored by the U.S. Department of Energy (DOE), Office of Environmental Management, Oak Ridge Operations (ORO) Office through a joint collaboration between United Cleanup Oak Ridge LLC (UCOR), Oak Ridge National Laboratory (ORNL), and The University of Tennessee, Ecology and Evolutionary Biology, The Institute for Environmental Modeling (TIEM). All rights reserved.
    https://rais.ornl.gov/
  9. ChEBI
  10. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  11. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  12. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  13. EPA Chemical and Products Database (CPDat)
  14. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  15. EPA Pesticide Ecotoxicity Database
  16. EU Pesticides Database
  17. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Acequinocyl
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  18. USDA Pesticide Data Program
  19. Hazardous Chemical Information System (HCIS), Safe Work Australia
  20. Regulation (EC) No 1272/2008 of the European Parliament and of the Council
    LICENSE
    The copyright for the editorial content of this source, the summaries of EU legislation and the consolidated texts, which is owned by the EU, is licensed under the Creative Commons Attribution 4.0 International licence.
    https://eur-lex.europa.eu/content/legal-notice/legal-notice.html
    acequinocyl (ISO); 3-dodecyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl acetate
    https://eur-lex.europa.eu/eli/reg/2008/1272/oj
  21. Japan Chemical Substance Dictionary (Nikkaji)
  22. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  23. Metabolomics Workbench
  24. Springer Nature
  25. Wikidata
  26. PubChem
  27. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  28. GHS Classification (UNECE)
  29. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  30. PATENTSCOPE (WIPO)
CONTENTS