Mandipropamid (Ref: NOA 446510)

Mandipropamid (Ref: NOA 446510)	Last updated: 12/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A new 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

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/07/2026

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Austria

Date EC 1107/2009 inclusion expires

31/07/2023

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
✓	✓	✓	✓	✓	✓	✓	✓	✓

Also used in

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 group

Mandelamide

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

CIPAC number

783

US EPA chemical code

036602

PubChem CID

11292824

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 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

Light beige powder

Formulations

Property

Value

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

Revus

Example products using this active

Syngenta

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)

Not expected to self ignite; Not highly flammable

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

1.58 X 10⁰³

Calculated

Log P

3.2

High

Bulk 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

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

3.7

Note

Published literature RL₅₀ range 2.2-5.3 days, 2 field crops, various matrices, n=2

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

16.1

Slightly mobile

K_foc

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

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.060

Minor fraction, Relevant

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

Soil

Minor fraction, Not relevant

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

Soil

Minor fraction, Not relevant

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

Soil

Minor fraction, Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

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

unknown

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

Rat (Faeces); Plant; Animal; Soil

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

0.100

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

unknown

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

unknown

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)

unknown

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

Sediment

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

Soil

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

unknown

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

unknown

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

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⁻¹ bw/Day

Colinus virginianus

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

83.6

Colinius virginianus NOEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 2.9

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.5

Pimephales promelas

Moderate

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

7.1

Daphnia magna

Moderate

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

0.87

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)

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

Non-target plants

> 450

Unknown species
Vegetative vigour, ER₅₀
as g ha⁻¹

> 450

Unknown species
Seedling emergence, ER₅₀
as g ha⁻¹

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

> 19.8

Anabaena flos-aquae

Low

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

Honeybees (Apis spp.)

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

> 200

Low

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

> 200

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)

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

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)

> 16.0

Eisenia foetida corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

827

Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

900

>
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 4.5 kg ha⁻¹ 28 days

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)

> 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

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

Eye irritant

Phototoxicant

No data found

General human health issues

Liver toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Environment: H400, H411

EC Risk Classification

N - Dangerous for the environment: R51, R53

EC Safety Classification

None

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

mandipropamid

French

mandipropamide

German

Mandipropamid

Danish

mandipropamid

Italian

mandipropamid

Spanish

mandipropamida

Greek

Polish

mandipropamid

Swedish

mandipropamid

Hungarian

Dutch

Record last updated:	12/01/2021
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