Iprovalicarb (Ref: SZX 0722)

Iprovalicarb (Ref: SZX 0722)	Last updated: 15/06/2024
(Also known as: SZX 722)

SUMMARY

Iprovalicarb is a systemic, protectant fungicide. It has a low aqueous solubility, is semi-volatile and there is some risk it may leach to groundwater. It is non-persistent in soil but may persist in water for a long time. It is moderately toxic to mammals but has a low risk of bioaccumulating. It is considered to be a carcinogen. It is moderately toxic to birds, most aquatic organisms and earthworms but is not toxic to honeybees.

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: GUS: Transition state; Drainflow: Moderately mobile	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Possible Carcinogen

GENERAL INFORMATION

Description

A carbamate/valinamide fungicide often used to control Oomycete pathogens

Example pests controlled

Downy mildew; Late blight

Example applications

Ornamentals; Potatoes; Grapes; Tomatoes

Efficacy & activity

Availability status

Current

Introduction & key dates

1999, introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/03/2031

GB LERAP status

No data

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Ireland/Italy

Date EC 1107/2009 inclusion expires

31/03/2031

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, Morocco

Chemical structure

Isomerism

A molecule with 2 chiral centres. Iprovalicarb is a mixture of two diastereoisomers, each consisting of only one enantiomer. The ratio of these two diastereoisomers A(S,R) and B(S,S) in technical material is approximately 1:1.

Chemical formula

C₁₈H₂₈N₂O₃

Canonical SMILES

CC1=CC=C(C=C1)C(C)NC(=O)C(C(C)C)NC(=O)OC(C)C

Isomeric SMILES

CC1=CC=C(C=C1)C(C)NC(=O)[C@H](C(C)C)NC(=O)OC(C)C

International Chemical Identifier key (InChIKey)

NWUWYYSKZYIQAE-WMCAAGNKSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H28N2O3/c1-11(2)16(20-18(22)23-12(3)4)17(21)19-14(6)15-9-7-13(5)8-10-15/h7-12,14,16H,1-6H3,(H,19,21)(H,20,22)/t14?,16-/m0/s1/f/h19-20H

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
iprovalicarb	Unstated isomer

General status

Pesticide type

Fungicide

Substance groups

Carbamate fungicide; Valinamide fungicide

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic with protective, curative and eradicative action. Cellulose synthesis inhibitor.

CAS RN

140923-17-7

EC number

604-209-3

CIPAC number

620

US EPA chemical code

098359

PubChem CID

10958189

CLP index number

616-232-00-6

Molecular mass

320.43

PIN (Preferred Identification Name)

IUPAC name

isopropyl 2-methyl-1-{[(RS)-1-p-tolylethyl]carbamoyl}-(S)-propylcarbamate

CAS name

1-methylethyl ((1S)-2-methyl-1-(((1-(4-methylphenyl)ethyl)amino)carbonyl)propyl)carbamate

Other status information

Marine pollutant

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

White-yellow powder

Formulations

Property

Value

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

Bayer CropScience

Example products using this active

Antracol
Melody

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

17.8

Low

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

5300

Toluene

41000

Acetone

20000

Ethyl acetate

132000

Dichloromethane

Melting point (°C)

164

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

160

Flashpoint (°C)

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

1.58 X 10⁰³

Calculated

Log P

3.2

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.11

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

7.90 X 10^-05

Low volatility

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

1.40 X 10^-06

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

No maxima between 290-400nm

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

15.5

Non-persistent

DT₅₀ (lab at 20 °C)

10.5

Non-persistent

DT₅₀ (field)

15.5

Non-persistent

DT₉₀ (lab at 20 °C)

Moderately persistent

DT₉₀ (field)

44.8

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 20-30 days, field studies DT₅₀ range 4.7-27 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

19.8

Note

Published literature RL₅₀ range 1.75-72.0 days, 2 field & undercover grown crops, various matrices, n=5

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

Stable

Note

Stable pH 5 to pH 9 at 25 °C

Water-sediment DT₅₀ (days)

181

Slow

Water phase only DT₅₀ (days)

Stable

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)

Moderately mobile

K_oc (mL g⁻¹)

106

Notes and range

EU dossier koc range 61-131 mL g⁻¹

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.35

Calculated

Transition state

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

Value

8.45 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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

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

1-(4-methylphenyl)ethylamine

Major fraction (aerobic)

0.507

Bayer verified

iprovalicarb-carboxylic acid

Major fraction (aerobic)

0.100

Bayer verified

N-[1-(4-methylphenyl)ethyl] acetamide

Major fraction (anaerobic)

0.291

Bayer verified

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)

1-(4-methylphenyl)ethylamine

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

N-acetyl-PMPA

Water; Sediment

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

196

Rat

Moderate

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 mg kg feed⁻¹

Colinus virginianus

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

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

> 1000

Eisenia foetida

Low

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

3.37

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose: 4.95 kg ha⁻¹

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

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

> 200

Apis mellifera

Low

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

> 199

Apis mellifera

Low

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

Chronic

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 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 at dose 0.46 kg ha⁻¹

-20.5

Aphidius rhopalosiphi Adult

Beneficial insects (Predatory mites) as % Mortality at dose 0.46 kg ha⁻¹

-3.4

Typhlodromus pyri Protonymph

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)

> 22.7

Oncorhynchus mykiss

Moderate

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

9.89

Oncorhynchus mykiss

Moderate

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

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

> 19.8

Unknown species

Moderate

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

1.89

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)

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

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

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

> 10

Raphidocelis subcapitata

Low

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.0

Rat

Other Mammal toxicity endpoints

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

0.015

Dog SF=200

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)

0.015

Dog 1 year SF=100

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

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

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

US EPA - likely to be human carcinogen; CLP data - suspected of causing cancer

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H351

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

UN2757

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Chemically stable under standard ambient conditions

TRANSLATIONS

Language

Name

English

iprovalicarb

French

iprovalicarbe

German

Iprovalicarb

Danish

iprovalicarb

Italian

iprovalicarb

Spanish

iprovalicarb

Greek

Polish

iprowalikarb

Swedish

Hungarian

iprovalikarb

Dutch

Norwegian

Record last updated:	15/06/2024
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