Mandipropamid (Ref: NOA 446510)

Mandipropamid (Ref: NOA 446510)	Last updated: 31/10/2024
(Not known by any other names)

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	Ecotoxicity Moderate alert: Birds acute ecotoxicity: Moderate; Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Mammals chronic toxicity: Moderate

GENERAL INFORMATION

Description

A fungicide used to control Oomycete pathogens on grapes, potatoes and other crops

Example pests controlled

Plasmopara viticola; Phytophthora infestans; Pseudoperonospora cubensis

Example applications

Grapes; Potatoes; Tomatoes; Curcubits

Efficacy & activity

Availability status

Current

Introduction & key dates

1999, discovered

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/07/2031

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Austria

Date EC 1107/2009 inclusion expires

31/12/2025

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

Iran, Morocco

Chemical structure

Isomerism

Mandipropamid is a chiral molecule with an asymmetrically substituted carbon atom and consists of a pair of enantiomers. The technical material is a racemate comprising equimolar amounts of (R)- and (S)-mandipropamid

Chemical formula

C₂₃H₂₂ClNO₄

Canonical SMILES

COC1=C(C=CC(=C1)CCNC(=O)C(C2=CC=C(C=C2)Cl)OCC#C)OCC#C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

KWLVWJPJKJMCSH-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C23H22ClNO4/c1-4-14-28-20-11-6-17(16-21(20)27-3)12-13-25-23(26)22(29-15-5-2)18-7-9-19(24)10-8-18/h1-2,6-11,16,22H,12-15H2,3H3,(H,25,26)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
mandipropamid	Unstated isomer

General status

Pesticide type

Fungicide

Substance groups

Amide fungicide

Minimum active substance purity

930 g kg⁻¹

Known relevant impurities

EU dossier - SYN 5455038 < 0.1g kg⁻¹

Substance origin

Synthetic

Mode of action

Inhibits spore germination with preventative action. Cellulose synthesis inhibitor.

CAS RN

374726-62-2

EC number

609-434-0

CIPAC number

783

US EPA chemical code

036602

PubChem CID

11292824

CLP index number

616-213-00-2

Molecular mass

411.9

PIN (Preferred Identification Name)

IUPAC name

(RS)-2-(4-chlorophenyl)-N-[3-methoxy-4-(prop-2-ynyloxy)phenethyl]-2-(prop-2-ynyloxy)acetamide

CAS name

4-chloro-N-(2-(3-methoxy-4-(2-propynyloxy)phenyl)ethyl)-a-(2-propynyloxy)benzeneacetamide

Other status information

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

Light beige powder

Formulations

Property

Value

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

Syngenta

Example products using this active

Revus
Carial star

Formulation and application details

Often supplied as soluble concentrate that is mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

4.2

Low

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

300000

Acetone

120000

Ethyl acetate

29000

Toluene

400000

Dichloromethane

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

200

Flashpoint (°C)

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

1.58 X 10⁰³

Calculated

Log P

3.2

at 25 °C

High

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data - studies showed low residue content in ruminant fat and no accumulation in milk.

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

9.40 X 10^-04

Low volatility

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

9.2 X 10^-05

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

Negligible

24 hr

From soil surface

8.9

24 hr

Volatilisation is not considered critical for air pollution

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

Neutral solution: 223nm = 20144, 276nm = 2724
Acidic solution: 223nm = 20313, 276nm = 2845
Basic solution: 223nm = 19414, 276nm = 2864

Surface tension (mN m⁻¹)

72.8

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

49.1

Moderately persistent

DT₅₀ (lab at 20 °C)

49.1

Moderately persistent

DT₅₀ (field)

13.6

Non-persistent

DT₉₀ (lab at 20 °C)

162

Persistent

DT₉₀ (field)

76.4

DT₅₀ modelling endpoint

Note

EU dossier lab studies range DT₅₀ 23.4-83.9 days, DT₉₀ range 102-285 days; field studies DT₅₀ range 5.6-29.2 days, DT₉₀ range 42.1-240 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

5.0

Note

Published literature RL₅₀ range 2.2-8.1 days, 3 field & undercover crops, various matrices, n=4

Aqueous photolysis DT₅₀ (days) at pH 7

Value

4.0

Moderately fast

Note

DT₅₀ 1.4-6.7 days sterilised water pH 7, 4.8 days natural summer light 40 deg N, slightly faster at pH 7.4

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

Value

Stable

Note

Stable pH 4 to pH 9

Water-sediment DT₅₀ (days)

12.2

Fast

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

16.1

Slightly mobile

K_foc (mL g⁻¹)

847

¹/_n

0.845

Notes and range

EU dossier K_f range 2.88-53.2 mL g⁻¹, K_foc range 405-1294 mL g⁻¹, ¹/_n range 0.780-0.916, Soils=7

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.22

Calculated

Low leachability

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

Value

2.09 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

1.36

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)

Low potential

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

2-(4-chlorophenyl)-2-hydroxy-N-(2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl)-acetamide (Ref: CGA 380778)

Minor fraction

0.060

(R/S)2-(4-chloro-phenyl)-2-hydroxy-N-(2-(4-hydroxy-3-methoxy-phenyl)-ethyl)-acetamide (Ref: CGA 380775)

Minor fraction

(R/S)(4-Chloro-phenyl)-prop-2-ynyloxy-acetic acid (Ref: SYN 500003)

Minor fraction

(R/S)allyloxy-(4-chloro-phenyl)-acetic acid (Ref: SYN 504851)

Minor fraction

2-(4-chlorophenyl)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide (Ref: NOA 458422)

N-[2-(4-allyloxy-3-methoxyphenyl)-ethyl]-2-(4-chloro-phenyl)-2-prop-2-ynyloxy-acetamide (Ref: SYN 536638)

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

2-(4-chlorophenyl)-N-[2-(3,4-dihydroxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide (Ref: SYN 505503)

2-allyloxy-N-[2-(4-allyloxy-3-methoxy-phenyl)-ethyl]-2-(4-chloro-phenyl)-acetamide (Ref: SYN 535839)

2-allyloxy-N-[2-(4-allyloxy-3-hydroxy-phenyl)-ethyl]-2-(4-chloro-phenyl)-acetamide (Ref: SYN 539679)

Water (Anaerobic); Water/sediment

2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethanamine (Ref: NOA 440567)

N-[2-(4-allyloxy-3-hydroxy-phenyl)-ethyl]-2-(4-chloro-phenyl)-2-prop-2-ynyloxy-acetamide (Ref: SYN 539678)

Sediment

(4-chlorophenyl)-hydroxy acetic acid (Ref: NOA 495119)

4-(2-aminoethyl)-2-methoxyphenol (Ref: CGA 353043)

2-(4-chlorophenyl)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide (Ref: NOA 458422)

Rat (Faeces); Plant; Animal

2-(4-chlorophenyl)-N-[2-(3-hydroxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide (Ref: SYN 521195)

Animal; Sediment

allyloxy-(4-chlorophenyl)-actic acid (Ref: SYN 504851)

Water/sediment

2-(4-chlorophenyl)-N-[2-(3,4-dihydroxy-phenyl)-ethyl]-2-hydroxyacetamide (Ref: SYN 505504)

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)

(ppm diet)

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

> 120

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 1000

Anas platyrhynchos

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 2141 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

83.6

Colinus virginianus NOEL

Moderate

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

> 500

Eisenia foetida corr

Moderate

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

> 16.0

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 4.5 kg ha⁻¹ 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

>= 20

Folsomia candida

Non-target plants

> 450

Unknown species
Vegetative vigour, ER₅₀
as g ha⁻¹

> 450

Unknown species
Seedling emergence, ER₅₀
as g ha⁻¹

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)

> 200

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 LR₅₀ g ha⁻¹

827

Aphidius rhopalosiphi

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

> 900

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)

> 2.9

Oncorhynchus mykiss

Moderate

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

0.5

Pimephales promelas

Moderate

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

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

7.1

Daphnia magna

Moderate

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

0.87

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)

> 4.4

Lemna gibba

Moderate

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

> 19.8

Anabaena flos-aquae

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)

5050

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.19

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.15

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)

0.17

Dog SF=100

Dermal penetration studies (%)

0.2-0.6

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for proposed uses

Occupational

Acceptable for proposed uses

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

GB MRL amemendments as of Sept 2023 for papayas

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

Eye irritant

Phototoxicant

No data found

General human health issues

Liver toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Environment: H400, H411

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

mandipropamid

French

mandipropamide

German

Mandipropamid

Danish

mandipropamid

Italian

mandipropamid

Spanish

mandipropamida

Greek

Polish

mandipropamid

Swedish

mandipropamid

Hungarian

Dutch

Norwegian

mandipropamid

Record last updated:	31/10/2024
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