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mandipropamid (Ref: NOA 446510)
** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for mandipropamid

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

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Austria
Date inclusion expires 31/07/2023
EU Candidate for substitution (CfS) No
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

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

Chemical structure: Click here for further information on the general chemical status information used on this site
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

Click to access the Cambridge Crystallographic Data Centre (CCDC) website
Cambridge Crystallographic Data Centre diagrams:
Common Name Relationship Link
Mandipropamid Unstated isomer Click here for the CCDC structure diagram

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Fungicide
Substance group Mandelamide
Minimum active substance purity 930 g/kg
Known relevant impurities EU dossier - SYN 5455038 < 0.1g/kg
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 (g mol-1) 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) 40
Examples of recorded resistance -
Physical state Light beige powder
Related substances & organisms -

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • Syngenta
Example products using this active
  • Revus
UK LERAP status None
Formulation and application details Often supplied as soluble concentrate that is mixed with water and used as a spray.


ENVIRONMENTAL FATE
for mandipropamid

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 4.2 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 300000 A5 - Acetone -
120000 A5 - Ethyl acetate -
29000 A5 - Toluene -
400000 A5 - Dichloromethane -
Melting point (oC) 96 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 200 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 1.58 X 1003 Calculated -
Log P 3.2 A5 High
Bulk density (g ml-1)/Specific gravity - - -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 9.40 X 10-04 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 9.2 X 10-05 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 1.81 Calculated Transition state
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 6.06 X 10-02 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated Medium
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 A5 -
Surface tension (mN m-1) 72.8 A5 at 20oC -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 49.1 A5 Moderately persistent
DT50 (lab at 20oC) 49.1 A5 Moderately persistent
DT50 (field) 13.6 A5 Non-persistent
DT90 (lab at 20oC) 162 A5 -
DT90 (field) 76.4 A5 -
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 R4 -
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 A3 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 20oC and pH 7 Value Stable A5 -
Note Stable pH 4 to pH 9
Water-sediment DT50 (days) 12.2 A5 Fast
Water phase only DT50 (days) Stable A5 -

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf 16.1 A5 Slightly mobile
Kfoc 847
1/n 0.845
Notes and range EU dossier Kf range 2.88-53.2 mL/g, Kfoc range 405-1294 mL/g, 1/n range 0.780-0.916, Soils=7
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 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-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethanamine
(Ref: NOA 440567) 		- 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 - -
(4-chlorophenyl)-hydroxy acetic acid
(Ref: NOA 495119) 		- unknown - -
allyloxy-(4-chlorophenyl)-actic acid
(Ref: SYN 504851) 		- Water/sediment 0.100 -
2-(4-chlorophenyl)-N-[2-(3,4-dihydroxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide
(Ref: SYN 505503) 		- unknown - -
2-(4-chlorophenyl)-N-[2-(3,4-dihydroxy-phenyl)-ethyl]-2-hydroxyacetamide
(Ref: SYN 505504) 		- unknown - -
2-(4-chlorophenyl)-N-[2-(3-hydroxy-4-prop-2-ynyloxy-phenyl)-ethyl]-2-prop-2-ynyloxy-acetamide
(Ref: SYN 521195) 		- Animal; Sediment - -
2-allyloxy-N-[2-(4-allyloxy-3-methoxy-phenyl)-ethyl]-2-(4-chloro-phenyl)-acetamide
(Ref: SYN 535839) 		- unknown - -
N-[2-(4-allyloxy-3-methoxyphenyl)-ethyl]-2-(4-chloro-phenyl)-2-prop-2-ynyloxy-acetamide
(Ref: SYN 536638) 		- Soil - -
N-[2-(4-allyloxy-3-hydroxy-phenyl)-ethyl]-2-(4-chloro-phenyl)-2-prop-2-ynyloxy-acetamide
(Ref: SYN 539678) 		- Sediment - -
2-allyloxy-N-[2-(4-allyloxy-3-hydroxy-phenyl)-ethyl]-2-(4-chloro-phenyl)-acetamide
(Ref: SYN 539679) 		- Water (Anaerobic); Water/sediment - -


ECOTOXICOLOGY
for mandipropamid

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 48 A5 Low potential
CT50 (days) 1 -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) - - -
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 1000 A5 Anas platyrhynchos Moderate
Birds - Short term dietary (LC50/LD50) > 2141 mg kg-1 bw/Day A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) > 2.9 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.5 A5 Pimephales promelas Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 7.1 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.87 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) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) - - -
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) > 4.4 A5 Lemna gibba Moderate
Non-target plants > 450 A4 Unknown species
Vegetative vigour, ER50
as g/ha 		-
> 450 A4 Unknown species
Seedling emergence, ER50
as g/ha 		-
Algae - Acute 72 hour EC50, growth (mg l-1) > 19.8 A5 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 A5 Low
Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) > 200 A5 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 A5 Eisenia foetida, corr Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) > 16.0 A5 Eisenia foetida, corr Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 827 A5 Aphidius rhopalosiphi -
% Effect - - -
Other arthropod (2) LR50 g ha-1 900 >
A5 Typhlodromus pyri 		-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect 		A5
Dose: 4.5 kg ha-1, 28 days 		-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION
for mandipropamid

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 5050 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 5.19 A5 Rat, 4 hr (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.15 A3 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) 0.17 A3 Dog, SF=100 -
Dermal penetration studies (%) 0.2-0.6 A5 concentration dependent -
Dangerous Substances Directive 76/464 - - -
Exposure Routes Public Acceptable for proposed uses
Occupational Acceptable for proposed uses
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Genotoxic Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

A3; B3; C3; D0; E3

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

General human health issues Liver toxicant
Key: Genotoxicity
A: Chromosome aberration (EFSA database)
B: DNA damage/repair (EFSA database)
C: Gene mutation (EFSA database)
D: Genome mutation (EFSA database)
E: Unspecified genotoxicity type (miscellaneous data source)
0: No data
1: Positive
2: Mixed/ambiguous results
3: Negative		 Key: Other
: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
CLP classification 2013 Environment: H400, H411
EC Risk Classification Click here to view information omn the EU risk phrases N - Dangerous for the environment: R51, R53
EC Safety Classification Click here to view information omn the EU safety phrases None
WHO Classification U - Unlikely to present an acute hazard
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS
for mandipropamid

Language Name
English mandipropamid
French mandipropamide
German Mandipropamid
Danish mandipropamid
Italian mandipropamid
Spanish mandipropamida
Greek -
Slovenian mandipropamid
Polish mandipropamid
Swedish mandipropamid
Hungarian -
Dutch -

Record last updated: Tuesday 25 June 2019
Contact: aeru@herts.ac.uk