Afidopyropen (Ref: ME5343)

Afidopyropen (Ref: ME5343)	Last updated: 16/12/2020
(Also known as: coprapidpen; BAS 440 I)

SUMMARY

Afidopyropen is a novel insecticide that does not have approval for use in the EU. It is moderately persistent in soil and water. It is moderately mobile and may leach to groundwaters. It has a favourable biodiversity toxcityl profile and is not highly toxic to bees. Whilst it has a low oral toxicity to mammals there are some conserns that afidopyropen may be carcinogenic.

GENERAL INFORMATION

Description

A novel insecticide that is effective against sucking insects

Example pests controlled

Aphids; Spidermites; Thrips; Psyllids; Mealybugs, Scale

Example applications

Fruit; Vegetables; Nuts; Cotton; ; Ornamentals

Efficacy & activity

Availability status

Current

Introduction & key dates

2013

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Not applicable

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; Australia

Chemical structure

Isomerism

Isomeric

Chemical formula

C₃₃H₃₉NO₉

Canonical SMILES

CC12CCC(C(C1CC(C3(C2C(C4=C(O3)C=C(OC4=O)C5=CN=CC=C5)O)C)O)(C)COC(=O)C6CC6)OC(=O)C7CC7

Isomeric SMILES

C[C@]12CC[C@@H]([C@@]([C@@H]1C[C@@H]([C@@]3([C@@H]2[C@H](C4=C(O3)C=C(OC4=O)C5=CN=CC=C5)O)C)O)(C)COC(=O)C6CC6)OC(=O)C7CC7

International Chemical Identifier key (InChIKey)

LRZWFURXIMFONG-HRSIRGMGSA-N

International Chemical Identifier (InChI)

InChI=1S/C33H39NO9/c1-31-11-10-24(42-29(38)18-8-9-18)32(2,16-40-28(37)17-6-7-17)22(31)14-23(35)33(3)27(31)26(36)25-21(43-33)13-20(41-30(25)39)19-5-4-12-34-15-19/h4-5,12-13,15,17-18,22-24,26-27,35-36H,6-11,14,16H2,1-3H3/t22-,23+,24+,26+,27-,31+,32+,33-/m1/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide

Substance group

Pyropene

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Disrupts insect feeding behaviour. A chlordotonal orgn TRPV (transient receptor potential vanilloid) channel modulatot

CAS RN

915972-17-7

EC number

CIPAC number

US EPA chemical code

7969

PubChem CID

54589430

Molecular mass

593.7

PIN (Preferred Identification Name)

IUPAC name

((3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-(cyclopropylcarbonyloxy)-1,2,3,4,4a,5,6,6a,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridyl)-11H,12H-benzo(f)pyrano(4,3-b)chromen-4-yl)methyl cyclopropanecarboxylate

CAS name

((3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-((cyclopropylcarbonyl)oxy)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho(2,1-b)pyrano(3,4-e)pyran-4-yl)methyl cyclopropanecarboxylate

Other status information

Relevant Environmental Water Quality Standards

Possible groundwater pollutants

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

Physical state

The technical maaterial is a yellow powder

Formulations

Property

Value

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

Sefina
Versys
Ventigra

Example products using this active

BASF

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

25.1

Low

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

55400

Toluene

500000

Methanol

500000

Acetone

500000

Ethyl acetate

Melting point (°C)

150

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

Not expected to self-ignite; Not highly flammable

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

2.82 X 10⁰³

Calculated

Log P

3.45

High

Bulk density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

9,99 X 10^-03

Low volatility

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

2.34 X 10^-04

Non-volatile

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

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

8.8

Non-persistent

DT₅₀ (lab at 20 °C)

8.8

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

General literature: aerobic DT₅₀ 2.7-18.6 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

Stable

Note

Stable at all environmntally relevant pH values

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

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

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

Value

Cannot be calculated

Note

Potential for particle bound transport index

Potential for loss via drain flow

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 802

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 18.3

Pimephales promelas

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

> 8.0

Daphnia magna

Moderate

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

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)

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)

> 200

Apis mellifea

Low

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

> 100

Apis mellifera

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

Eisenia foatida

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

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Soil micro-organisms

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)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.48

Rat

Other Mammal toxicity endpoints

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

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

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

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

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

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

No information available

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

EC Risk Classification

EC Safety Classification

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

afidopyropen

French

afidopyropene

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	16/12/2020
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