Acrinathrin (Ref: RU38702)

Acrinathrin (Ref: RU38702)	Last updated: 12/01/2021
(Also known as: acrinathrine; AE F076003; HOE 76003; NU 702)

SUMMARY

Acrinathrin is a synthetic pyrethroid that has a high insecticidal activity against a range of insects including mites and which is approved for use in the EU. It has a low aqueous solubility, is semi-volatile and, based on its chemical properties, should not leach. Laboratory studies suggest it is moderately persistent in soils but will rapid degrade in aqueous systems. It has a low toxicity to humans but there is some concern that it may bio-accumulate. Acrinathrin is highly toxic to bees and most aquatic species, moderately toxic to birds and earthworms.

GENERAL INFORMATION

Description

A pyrethroid ester insecticide and acaricide effective against a range of phytophagous mites and other insects

Example pests controlled

Psyllid; Two-spotted spider mites; Thrips; Leafminers; Aphids

Example applications

Potatoes; Tomatoes; French and runner beans

Efficacy & activity

Availability status

Current

Introduction & key dates

1990, France

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

Not applicable

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

France

Date EC 1107/2009 inclusion expires

31/12/2023

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

Chemical structure

Isomerism

Acrinathrin contains three chiral centres and one double bond, giving a total of 15 potential isomers other than acrinathrin (8 enantiomeric pairs where acrinathrin is one isomer of an enantiomeric pair).

Chemical formula

C₂₆H₂₁F₆NO₅

Canonical SMILES

CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=CC(=O)OC(C(F)(F)F)C(F)(F)F)C

Isomeric SMILES

CC1([C@H]([C@H]1C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)/C=C\C(=O)OC(C(F)(F)F)C(F)(F)F)C

International Chemical Identifier key (InChIKey)

YLFSVIMMRPNPFK-WEQBUNFVSA-N

International Chemical Identifier (InChI)

InChI=1S/C26H21F6NO5/c1-24(2)18(11-12-20(34)38-23(25(27,28)29)26(30,31)32)21(24)22(35)37-19(14-33)15-7-6-10-17(13-15)36-16-8-4-3-5-9-16/h3-13,18-19,21,23H,1-2H3/t18-,19+,21-/m0/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide, Acaricide

Substance group

Pyrethroid

Minimum active substance purity

970 g kg⁻¹

Known relevant impurities

EU dossier - 1,3-dicyclohexylurea <2mg kg⁻¹

Substance origin

Synthetic

Mode of action

Contact and stomach action. Neurotoxin.

CAS RN

101007-06-1

EC number

CIPAC number

678

US EPA chemical code

PubChem CID

6436606

Molecular mass

541.44

PIN (Preferred Identification Name)

(S)-cyano(3-phenoxyphenyl)methyl (1R,3S)-3-{(1Z)-3-[(1,1,1,3,3,3-hexafluoropropan-2-yl)oxy]-3-oxoprop-1-en-1-yl}-2,2-dimethylcyclopropane-1-carboxylate

IUPAC name

(S)-α-cyano-3-phenoxybenzyl (Z)-(1R)-cis-2,2-dimethyl-3-[2-(2,2,2-trifluoro-1-trifluoromethylethoxycarbonyl)vinyl]cyclopropanecarboxylate

CAS name

(S)-cyano(3-phenoxyphenyl)methyl (1R,3S)-2,2-dimethyl-3-[(1Z)-3-oxo-3-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]-1-propenyl]cyclopropanecarboxylate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Frankliniella occidentalis, Tetranychus urticae

Physical state

White to beige coloured powder

Formulations

Property

Value

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

Rufast

Example products using this active

Cheminova

Formulation and application details

An oil-water emulsion concentrate usually diluted with water and applied as a foliar spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.0022

Low

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

400000

Xylene

17500

n-Hexane

61400

Ethanol

700000

Acetone

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

230

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.00 X 10⁰⁶

Calculated

Log P

6.3

High

Bulk density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

4.40 X 10^-05

Low volatility

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

1.80 X 10^-02

Non-volatile

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

Neutral solution 291nm = 466
Acidic solution 291nm = 642
Basic solution 308nm = 1760

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

39.2

Moderately persistent

DT₅₀ (lab at 20 °C)

40.6

Moderately persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

208.5

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range: 8.5-111.4 days, DT₉₀ range 28.2-887.1 days; General literature gives DT₅₀ range 9-37 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

2.6

Note

Published literature RL₅₀ range 1.2-6.9 days, 3 undercover crops, various matrices, n=4

Aqueous photolysis DT₅₀ (days) at pH 7

Value

2.3

Moderately fast

Note

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

Value

Stable

Note

Stable in acid media. Hydrolysis becomes more important as pH and temp increases: DT₅₀ 30 days at pH 7, 30 °C, 15 days at pH 9, 20 °C, <2 days pH9, 37 °C

Water-sediment DT₅₀ (days)

18.6

Fast

Water phase only DT₅₀ (days)

6.5

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

744

Non-mobile

K_oc

48231

Notes and range

EU dossier K_d range 302-1350 mL g⁻¹, K_oc range 24108-90061 mL g⁻¹, Soils=5

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.92

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

cis-des-hexafluoroisopropyl acrinathrin (Ref: DP-A)

Soil

0.097

Major fraction, Relevant

(2Z)-3-(3-((2-amino-2-oxo-1-(3-phenoxyphenyl)ethoxy)carbonyl)-2,2-dimethylcyclopropyl)prop-2-enoic acid

Soil

0.105

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

unknown
Note: Minor metabolite

3-PBAc

Soil; Surface water

Soil: 0.076

cyclopropyl-di-acid (Ref: RU 50158)
Note: Minor metabolite

DP-DPB-A

Animal (Urinary); Plant

Soil: 0.076

A-A
Note: DT50 7.4 days; Koc 88880

Soil

0.057

alphaR A-A

Soil

0.029

1,3-dicyclohexylurea (Ref: AEB007816)

Impurity

3-PBAld

Groundwater

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

538

Threshold for concern

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

2.4

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

1000 mg kg feed⁻¹

Anas platyrhynchos

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0061

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.00043

Cyprinus carpio

High

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

0.000022

Daphnia magna

High

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

0.0000032

Daphnia magna

High

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

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

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

0.000031

Chironomus riparius whole system

High

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

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

Non-target plants

888

Mungbean
Vegetative vigour, ER₅₀
as g ha⁻¹

> 1000

Mungbean
Seedling emergence, ER₅₀
as g ha⁻¹

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

0.0035

Selenastrum capricornutum

High

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)

0.084

High

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

0.077

High

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)

> 100

Eisenia foetida

Moderate

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

1.6

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

1.0

Folsomia candida 28d

Other arthropod (1)

LR₅₀ g ha⁻¹

0.046

Mortality
Alphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

0.006

Mortality
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 1 mg kg⁻¹ soil 28 days

Mesocosm study data

NOEAEC mg l⁻¹

0.000026

Micro-invertebrates NOEC

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

1.21

Rat 4 hr (whole body)

Other Mammal toxicity endpoints

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

0.01

Rat SF=100

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

0.01

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)

0.007

Rat SF=100

Dermal penetration studies (%)

2.0-8.3

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

No unacceptable risks to bystanders identified as long as access to spray area prohibited during spraying

Occupational

Risks identified - protective clothing and equipment advised

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

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

May cause diarrhoea and vomiting if ingested
Possible kidney and blood toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H332
Environment: H400, H410

EC Risk Classification

Carcinogen category 3: R40
Xn - Harmful: R21, R20
N - Dangerous for the environment: R50/53

EC Safety Classification

S1/2, S24, S36/37, S45, S46, S60, S61

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

acrinathrin

French

acrinathrine

German

Acrinathrin

Danish

acrinathrin

Italian

acrinatrina

Spanish

acrinatrina

Greek

Polish

akrynatryna

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