iprodione (Ref: ROP 500F) ** glycophene ** NRC 910 ** Translations

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GENERAL INFORMATION
for iprodione

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

EC Regulation 1107/2009 (repealing 91/414):

Status	Not approved
Dossier rapporteur/co-rapporteur	France/Belgium
Date inclusion expires	Expired
EU Candidate for substitution (CfS)	No
Listed in EU database	Yes

Approved for use () or known to be used () in the following European countries:

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

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)
Structure diagram/image available?	Yes

General status:

Pesticide type	Fungicide
Substance group	Dicarboximide
Minimum active substance purity	960 g/kg
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 (g mol-1)	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)	2
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	AgriGuard BASF Headland Rhone-Poulenc
Example products using this active	Rovral WG Surpass Governor 3336Plus Chipco Green
UK LERAP status	None
Formulation and application details	Often supplied as a soluble concentrate or wettable granules.

ENVIRONMENTAL FATE
for iprodione

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		6.8	A5	Low
Solubility - In organic solvents at 20oC (mg l-1)		590	A5 - Hexane	-
		147000	A5 - Toluene	-
		342000	A5 - Acetone	-
		225000	A5 - Ethyl acetate	-
Melting point (oC)		134	A5	-
Boiling point (oC)		-	-	-
Degradation point (oC)		233	A4	-
Flashpoint (oC)		150	A3	-
Octanol-water partition coefficient at pH 7, 20oC	P	1.00 X 1003	Calculated	-
	Log P	3.0	A4 - @ 25 DegC	Moderate
Bulk density (g ml-1)/Specific gravity		1.0	L3	-
Dissociation constant (pKa) at 25oC		Not applicable	A5	-
		Note: No dissociation
Vapour pressure at 20oC (mPa)		0.0005	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		7.00 X 10-06	A5	Non-volatile
GUS leaching potential index		0.58	Calculated	Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	1.09 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Medium
Maximum UV-vis absorption L mol-1 cm-1		204.5nm = 44333, 295nm in acetonitrile = <10	A5	-
Surface tension (mN m-1)		73	A5	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	36.2	A5	Moderately persistent
	DT50 (lab at 20oC)	26.2	A5	Non-persistent
	DT50 (field)	11.7	A5	Non-persistent
	DT90 (lab at 20oC)	126.8	A5	-
	DT90 (field)	73.2	A5	-
	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	R4	-
	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	R4	-
	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	67	A5	Stable
	Note	pH sensitive: DT50 67 days at pH 5, 1 hour at pH 9, 25 degC simulated sunlight
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	4.5	A5	Non-persistent
	Note	pH sensitive: DT50 140 days at pH 5, 0.2 days at pH 8
Water-sediment DT50 (days)		4.0	A5	Fast
Water phase only DT50 (days)		2.0	A5	Moderately fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	DW3	Slightly mobile
	Koc	700
	Notes and range	-
Freundlich	Kf	16.36	A5	Slightly mobile
	Kfoc	3927
	1/n	0.889
	Notes and range	EU dossier Kf range 2.16-43.1 mL/g, Kfoc range 223-2056 mL/g, 1/n range 0.70-0.96, Soils=9
pH sensitivity		No

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
for iprodione

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	70	A5 Whole fish	Low potential
	CT50 (days)	Not available		-
Mammals - Acute oral LD50 (mg kg-1)		> 2000	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	31	A5 Rat	High
	(ppm diet)	300		-
Birds - Acute LD50 (mg kg-1)		> 2000	A5 Colinus virginianus	Low
Birds - Short term dietary (LC50/LD50)		> 5620 mg kg feed-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		3.7	A5 Lepomis macrochirus	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		4.1	A5 Oncorhynchus mykiss	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		0.66	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.17	A5 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	A5 Chironomus riparius	Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1)		-	-	-
Aquatic plants - Acute 7 day EC50, biomass (mg l-1)		1	F3 Lemna gibba	Moderate
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC50, growth (mg l-1)		1.8	A5 Raphidocelis subcapitata	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		3.2	Q2 Unknown species	Low
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	> 200	A5	Low
	Oral acute 48 hour LD50 (μg bee-1)	> 25	A5	Moderate
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		> 1000	A5 Eisenia foetida	Low
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		-	-	-
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	-9.0	Beneficial capacity Dose:0.75 kg ha-1 A5 Aphidius rhopalosiphi, adult	-
Other arthropod (2)	LR50 g ha-1	-	-	-
	% Effect	84.3	Beneficial capacity Dose: 0.75 kg ha-1 A5 Typhlodromus pyri, protonymph	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 10 mg kg-1 soil	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for iprodione

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mammals - Acute oral LD50 (mg kg-1)		> 2000	A5 Rat	Low
Mammals - Dermal LD50 (mg kg-1 body weight)		> 2000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 5.16	A5 Rat. 4 hr (whole body)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.06	A5 Rat, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		None allocated	A5	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.3	A5 Rat, 90 day, SF=100	-
Dermal penetration studies (%)		0.2-12	A5 concentration dependent	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	No unacceptable risks to bystanders identified
	Occupational	Potential risk identified - PPE/PPC advised
European MRLs		Click here for the EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l-1)		-	-	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant
Respiratory tract irritant	Skin irritant	Skin sensitiser	Eye irritant	Phototoxicant
		-		-
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

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:

Property		Value	Source/Quality Score/Other Information	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
US EPA Classification (formulation)		III	-	Caution - Slightly toxic
UN Number		Variable with product, usually 3077 or 3082
Waste disposal & packaging		Packaging Group III (minor danger)

TRANSLATIONS
for iprodione

Language	Name
English	iprodione
French	iprodione
German	Iprodion
Danish	iprodion
Italian	iprodione
Spanish	iprodiona
Greek	iprodione
Slovenian	iprodion
Polish	iprodion
Swedish	iprodion
Hungarian	iprodion
Dutch	iprodion

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Record last updated: Wednesday 23 May 2018
Contact: aeru@herts.ac.uk