Iprodione (Ref: ROP 500F)

Iprodione (Ref: ROP 500F)	Last updated: 22/08/2024
(Also known as: glycophene; NRC 910)

SUMMARY

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: Drainflow: Slightly mobile; Potential for particle bound transport: Medium	Ecotoxicity Moderate alert: Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate	Human health High alert: Endocrine disrupter; Reproduction/development effects

GENERAL INFORMATION

Description

A post-harvest fungicide used to control diseases on fruit, vegetables and other crops

Example pests controlled

Botrytis, Minilia, Rhizoctonia, Sclerotinia - damping-off

Example applications

Vegetables including carrots; Lettuce; Ornamentals; Fruit including apples, pears, plums, apricots and peaches; Root crops; Cotton; Sunflowers; Turf

Efficacy & activity

Availability status

Current

Introduction & key dates

1997, first reported

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

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

France/Belgium

Date EC 1107/2009 inclusion expires

Expired

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
	✓	✓

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway

Additional information

Also used in

Egypt

Chemical structure

Isomerism

A structural isomer (RP-30228) exists which is also a major metabolite

Chemical formula

C₁₃H₁₃Cl₂N₃O₃

Canonical SMILES

CC(C)NC(=O)N1CC(=O)N(C1=O)C2=CC(=CC(=C2)Cl)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

ONUFESLQCSAYKA-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C13H13Cl2N3O3/c1-7(2)16-12(20)17-6-11(19)18(13(17)21)10-4-8(14)3-9(15)5-10/h3-5,7H,6H2,1-2H3,(H,16,20)

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Dicarboximide fungicide; Dichlorophenyl fungicide; Dichlorophenyl dicarboximide fungicide

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Contact action with protectant and some eradicant activity. Signal transduction inhibitor.

CAS RN

36734-19-7

EC number

253-178-9

CIPAC number

278

US EPA chemical code

109801

PubChem CID

37517

CLP index number

616-054-00-9

Molecular mass

330.17

PIN (Preferred Identification Name)

IUPAC name

3-(3,5-dichlorophenyl)-N-isopropyl-2,4-dioxoimidazolidine-1-carboxamide

CAS name

3-(3,5-dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide

Other status information

Chemical subject to PIC regulations: GB Part 2

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

Physical state

Colourless crystals

Formulations

Property

Value

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

AgriGuard
BASF
Headland
Rhone-Poulenc

Example products using this active

Rovral WG
Surpass
Governor
3336Plus
Chipco Green

Formulation and application details

Often supplied as a soluble concentrate or wettable granules

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

6.8

Low

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

590

Hexane

147000

Toluene

342000

Acetone

225000

Ethyl acetate

Melting point (°C)

134

Boiling point (°C)

Degradation point (°C)

233

Flashpoint (°C)

150

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

9.77 X 10⁰²

Calculated

Log P

2.99

at 25 °C

Moderate

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

1.0

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

5.1 X 10^-04

Low volatility

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

7.00 X 10^-06

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

Negligible

24 hr

From soil surface

0.1

24 hr

Volatilisation is not considered critical for air pollution

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

204.5nm = 44333, 295nm in acetonitrile = <10

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

36.2

Moderately persistent

DT₅₀ (lab at 20 °C)

26.2

Non-persistent

DT₅₀ (field)

11.7

Non-persistent

DT₉₀ (lab at 20 °C)

126.8

Persistent

DT₉₀ (field)

73.2

DT₅₀ modelling endpoint

Note

EU dossier (DAR 2016) Lab studies DT₅₀ range 13.4-36.2 days; DT₉₀ range 53.9-126.8 days, Soils= 6; Field studies DT₅₀ range 3.5-35.3 days, DT₉₀ range 29.0-196.9 days, Soils = 5; Other sources: DT₅₀ 14 days (DW4)

Dissipation rate RL₅₀ (days) on plant matrix

Value

9.7

Note

Published literature RL₅₀ range 2.5-51.2 days, 8 field & undercover grown crops, various matrices, n=14

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

8.7

Note

Published literature RL₅₀ range 3.3-23.1 days, 8 field & undercover grown crops, various matrices, n=9

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

pH sensitive: DT₅₀ 67 days at pH 5, 1 hour at pH 9, 25 °C simulated sunlight

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

Value

4.5

Non-persistent

Note

pH sensitive: DT₅₀ 140 days at pH 5, 0.2 days at pH 8

Water-sediment DT₅₀ (days)

4.0

Fast

Water phase only DT₅₀ (days)

2.0

Moderately fast

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Slightly mobile

K_oc (mL g⁻¹)

700

Notes and range

Freundlich

K_f (mL g⁻¹)

16.36

Slightly mobile

K_foc (mL g⁻¹)

3927

¹/_n

0.889

Notes and range

EU dossier K_f range 2.16-43.1 mL g⁻¹, K_foc range 223-2056 mL g⁻¹, ¹/_n range 0.70-0.96, Soils=9

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.43

Calculated

Low leachability

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

Value

8.20 X 10^-03

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

14.04

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

3-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine (Ref: RP25040)

Minor fraction

0.078

1-(3,5-dichlorophenyl)-5-isopropyl biuret (Ref: RP 36221)

Major fraction

0.127

N-(3,5-dichlorophenylcarbamoyl)-N-isopropylcarbamoyl-glycine (Ref: RP35606)

Major fraction

0.255

3,5-dichloroaniline (Ref: RP32596)

Major fraction

0.126

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

N-(3,5-dichlorophenyl)3-isopropyl-2,4-dioxoimidazoline-1-carboxamide (Ref: RP-30228)

Relevant

N-(3,5-dichlorophenylcarbamoyl)-N-isopropylcarbamoyl-glycine (Ref: RP35606)

Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

1-[(3,5-dichlorophenyl)carbamoymethyl]-3-isopropylurea (Ref: RP 37176)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

300

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

135.6

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5620 mg kg feed⁻¹

Colinus virginianus

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

22.3

Colinus virginianus NOEL

Moderate

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

> 500

Eisenia foetida corr

Moderate

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

500

Eisenia foetida corr

Low

Soil micro-organisms

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

Dose: 10 mg kg⁻¹ soil

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

750

Folsomia candida corr

Non-target plants

Honeybees (Apis spp.)

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

> 100

Apis mellifera

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)

Chronic as 10-day LDD₅₀ µg bee⁻¹ day⁻¹

166

Apis mellifera

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)

> 125

Osmia lignaria

Low

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

> 125

Osmia lignaria

Low

Other bee species (1)

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

Mode of exposure

Other bee species (2)

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

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

> 6750

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

> 6750

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

3.7

Lepomis macrochirus

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

4.1

Oncorhynchus mykiss

Moderate

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 2.26

Danio rerio Larva

Moderate

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

0.66

Daphnia magna

Moderate

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

0.17

Daphnia magna

Moderate

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (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)

0.1

Chironomus riparius

Moderate

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

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

Lemna gibba

Moderate

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

1.8

Raphidocelis subcapitata

Moderate

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

3.2

Unknown species

Low

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)

> 5.16

Rat. 4 hr (whole body)

Other Mammal toxicity endpoints

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

0.02

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

0.06

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

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

0.04

Dermal penetration studies (%)

0.2-12

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

Potential risk identified - PPE/PPC advised

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

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 pulmanary problems
Possible liver, adrenals, testes, postrate & spleen toxicant
Hepatotoxic in mice
US EPA - likely to be human carcinogen; CLP data - suspected carcingen
Endocrine issues - Increase weakly aromatase activity

Handling issues

Property

Value and interpretation

General

Prevent generation of mists
IMDG Transport Hazard Class 9
Not explosive or oxidising
Incompatible with strong oxidizing agents

CLP classification 2013

Health: H351
Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Chemically stable under standard ambient conditions

TRANSLATIONS

Language

Name

English

iprodione

French

iprodione

German

Iprodion

Danish

iprodion

Italian

iprodione

Spanish

iprodiona

Greek

iprodione

Polish

iprodion

Swedish

iprodion

Hungarian

iprodion

Dutch

iprodion

Norwegian

Record last updated:	22/08/2024
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