Acequinocyl

Acequinocyl	Last updated: 12/01/2021
(Also known as: kanemite)

SUMMARY

Acequinocyl is an acaricide that is currently being evaluated for EU use. It is not highly soluble in water but is highly soluble in most organic solvents. It is volatile. It is not expected to leach to groundwater. It is not mobile and tends not to be persistence in soil or aquatic systems. It has a low mammalian toxicity and there is some concern regarding its potential for bioaccumulation. Acequinocyl is moderately toxic to birds, fish, honeybees and earthworms and highly toxic to aquatic invertebrates.

GENERAL INFORMATION

Description

An unclassified acaricide effective against all mite development stages on, for example, ornamentals and top fruit

Example pests controlled

Mites including spider mites, spruce spider mite and red palm mite; Ticks

Example applications

Greenhouse crops; Ornamentals; Nursery crops; Fruits including strawberries, apples, pears, apricots, plums, grapes, citrus; Tree nuts; Pistachios

Efficacy & activity

Availability status

Current

Introduction & key dates

1999, Japan and Korea

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/08/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Netherlands

Date EC 1107/2009 inclusion expires

31/08/2024

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece
✓	✓		✓	✓	✓			✓
ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg
✓		✓				✓		✓
LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia
		✓	✓				✓

Also used in

USA

Chemical structure

Isomerism

None

Chemical formula

C₂₄H₃₂O₄

Canonical SMILES

CCCCCCCCCCCCC1=C(C(=O)C2=CC=CC=C2C1=O)OC(=O)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

QDRXWCAVUNHOGA-UHFFFAOYSA-N

International Chemical Identifier (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

2D structure diagram/image available?

Yes

General status

Pesticide type

Acaricide

Substance group

Unclassified

Minimum active substance purity

96%

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Mainly contact action but some via ingestion. Mitochondrial complex III electron transport inhibitor.

CAS RN

57960-19-7

EC number

CIPAC number

760

US EPA chemical code

006329

PubChem CID

93315

Molecular mass

384.51

PIN (Preferred Identification Name)

3-dodecyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl acetate

IUPAC name

3-dodecyl-1,4-dihydro-1,4-dioxo-2-naphthyl acetate

CAS name

2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

20B

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Plutella xylostella

Physical state

Pale yellow to light brown powdery flakes

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Kanemite

Example products using this active

Formulation and application details

Foliar spray application

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

0.007

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

250000

Xylene

250000

Dichloroethane

29200

1-Octanol

6100

Methanol

Melting point (°C)

59.6

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

200

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

Octanol-water partition coefficient at pH 7, 20 °C

1.58 X 10⁰⁶

Calculated

Log P

6.2

High

Bulk density (g ml⁻¹)

1.13

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

1.69 X 10^-03

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

9.7 X 10^-02

Non-volatile

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Acidic solution: 242nm = 16524, 248nm = 16989, 270nm = 13905, 335nm = 2836
Neutral solution: 242nm = 16582, 248nm = 16873, 270nm = 13207, 271nm = 2851
Basic solution: 232nm = 19055, 245nm = 13149, 275nm = 2172, 362nm = 8999

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

2.0

Non-persistent

DT₅₀ (lab at 20 °C)

2.0

Non-persistent

DT₅₀ (field)

0.1

Non-persistent

DT₉₀ (lab at 20 °C)

6.3

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 1.1-2.7 days, DT₉₀ 3.6-8.9 days; field studies DT₅₀ range 2-3 hours; Other sources: pH sensitive. DT₅₀ in alkaline soils < 2 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

1.6

Note

Perilla leaves, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.02

Fast

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

2.2

Non-persistent

Note

DT₅₀ pH sensitive: 74 days at pH 4, 67 minutes at pH 9

Water-sediment DT₅₀ (days)

0.45

Fast

Water phase only DT₅₀ (days)

0.5

Fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

1027

Non-mobile

K_oc

66033

Notes and range

EU dossier K_d range 678-1620 mL g⁻¹, K_oc range 3390-123000 mL g⁻¹ (later dossier gives range as 39900-123000 mL g⁻¹), Soils=4

Freundlich

K_f

Non-mobile

K_foc

100666

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.00

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

5.35 X 10^-03

Calculated

Note

Estimated concentrations of chemicals with Koc values greater than 9995 ml g⁻¹ are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

2-dodecyl-3-hydroxy-1,4-naphthoquinone

Soil

0.338

Major fraction, Relevant

2-(1',2'-dioxotetradecyl)benzoic acid (Ref: AKM-18)

Soil

0.219

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

2-(carboxycarbonyl)benzoic acid
Note: Low risk to fish

CBAA

Surface Water

0.11

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

366

Threshold for concern

CT₅₀ (days)

0.7

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 4855

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 1942

Anas platyrhynchos

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 847 mg kg bw⁻¹ day⁻¹

Coturnix japonica

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 100

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.52

Oncorhynchus mykiss 88 day

Moderate

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.0039

Daphnia magna

High

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.00098

Daphnia magna

High

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

0.00093

Americamysis bahia

High

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.479

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Non-target plants

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Low

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other pollinators (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other pollinators (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 1000

Low

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Mortality [Dose: 1.05 kg ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

8.52

Mortality [Dose: 0.3 kg ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 5.25 kg ha⁻¹

Mesocosm study data

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

Intermediate (class II)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 4855

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.84

Rat 4 hr (aerosol nose only)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.023

proposed Rat SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.08

proposed Rat SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.014

proposed Rat SF=100

Dermal penetration studies (%)

16.7

Dangerous Substances Directive 76/464

Exposure Routes

Public

Exposure by any route is unlikely
Source: US EPA/A5

Occupational

Small risk of dermal short-term exposure
Risk of chronic exposure is low
Source: US EPA/A5

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Blood toxicant

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H370, H317; H373
Environment: H400, H410

EC Risk Classification

T - Toxic: R39/23
Xn - Harmful: R43
N - Dangerous for the environment: R50, R53

EC Safety Classification

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

acequinocyl

French

acequinocyl

German

Acequinocyl

Danish

acequinocyl

Italian

acequinocil

Spanish

acequinocil

Greek

Polish

acekwinocyl

Swedish

Hungarian

Dutch

Record last updated:	12/01/2021
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242