Iprodione (Ref: ROP 500F)

Iprodione (Ref: ROP 500F)	Last updated: 11/11/2019
(Also known as: glycophene; NRC 910)

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 approval status

Approved

EC Regulation 1107/2009 (repealing 91/414)

EC Directive 91/414 Status

Not approved

Dossier rapporteur/co-rapporteur

France/Belgium

Date inclusion expires

Expired

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) or known to be used (#) in the following EU-27 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

Australia, USA

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 group

Dicarboximide

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

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

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

Physical state

Colourless crystals

Related substances & organisms

thiophanate-methyl

solvent naphtha

Formulations

Property

Value

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

Rovral WG
Surpass
Governor
3336Plus
Chipco Green

Example products using this active

AgriGuard
BASF
Headland
Rhone-Poulenc

UK LERAP status

None

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

1.00 X 10⁰³

Calculated

Log P

3.0

at 25 °C

Moderate

Bulk density (g ml⁻¹)

1.0

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.0005

Low volatility

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

7.00 X 10^-06

Non-volatile

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

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 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 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Slightly mobile

K_oc

700

Notes and range

Freundlich

K_f

16.36

Slightly mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.295

Major fraction, Relevant (anaerobic soils)

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

Soil

0.127

Major fraction, Relevant

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

Soil

0.255

Major fraction, Relevant

3,5-dichloroaniline (Ref: RP32596)

Soil

0.126

Major fraction, Relevant

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

Soil

0.078

Minor fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

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

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

300

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5620 mg kg feed⁻¹

Colinus virginianus

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

3.7

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

4.1

Oncorhynchus mykiss

Moderate

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

0.66

Daphnia magna

Moderate

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

0.17

Daphnia magna

Moderate

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

Non-target plants

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

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)

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 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)

> 500

Eisenia foetida corr

Moderate

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

500

Eisenia foetida corr

Low

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

750

Folsomia candida corr

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

-9.0

Beneficial capacity [Dose:0.75 kg ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

84.3

Beneficial capacity [Dose: 0.75 kg ha⁻¹]
Typhlodromus pyri protonymph

Soil micro-organisms

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

Dose: 10 mg kg⁻¹ soil

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)

0.06

Rat SF=100

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

None allocated

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

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

0.3

Rat 90 day SF=100

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

European MRLs

EU MRL pesticide database

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 pulmanary problems
Possible liver, adrenals, testes, postrate & spleen toxicant
Hepatotoxic in mice
USEPA - probable human carcinogen
Endocrine issues - Increase weakly aromatase activity

Handling issues

Property

Value and interpretation

General

Prevent generation of mists
IMDG Transport Code is usually 9
Not explosive or oxidising

CLP classification 2013

Health: H351
Environment: H400, H410

EC Risk Classification

Carcinogen category 3: R40
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S36/37, S60, S61

WHO Classification

III (Slightly hazardous)

UN Number

Variable with product, usually 3077 or 3082

Waste disposal & packaging

Packaging Group III (minor danger)

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

Record last updated:	11/11/2019
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