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napropamide-M
** 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 napropamide-M

Description: A soil applied herbicide for pre-emergence control of weeds in a range of crops including oilseed rape, fruit and woody ornamentals

Example pests controlled: Annual grasses; broad-leaved weeds

Example applications: Vegetables including brassicas, Fruit tree and bushes; Vines; Tobacco; Olives; Sunflowers; Turf; Oilseed rape; Ornamentals

Efficacy & activity: Efficiacy demonstrated during reported field trials

Availability status: Current

Introduction & key dates: circa 1970 as generic isomer mix

EC Regulation 1107/2009 (repealing 91/414):
Status Pending
Dossier rapporteur/co-rapporteur UK
Date inclusion expires -
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 Napropamide is a chiral molecule that exists in the R- and S-forms. Napropamide-M is the biologically active R-isomer.
Chemical formula C17H21NO2
Canonical SMILES CCN(CC)C(=O)C(C)OC1=CC=CC2=CC=CC=C21
Isomeric SMILES CCN(CC)C(=O)[C@@H](C)OC1=CC=CC2=CC=CC=C21
International Chemical Identifier key (InChIKey) WXZVAROIGSFCFJ-CYBMUJFWSA-N
International Chemical Identifier (InChI) InChI=1S/C17H21NO2/c1-4-18(5-2)17(19)13(3)20-16-12-8-10-14-9-6-7-11-15(14)16/h6-13H,4-5H2,1-3H3/t13-/m1/s1
2D structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Herbicide
Substance group Amide
Minimum active substance purity 930 g/Kg
Known relevant impurities EU 2017 dossier: None declared
Substance origin Synthetic
Mode of action Selective, systemic, absorbed through roots and translocated. Acts by preventing root cell elongation and so disrupting growth. Inhibition of VLCFA (inhibition of cell division).
CAS RN 41643-35-0
EC number -
CIPAC number 271
US EPA chemical code -
PubChem CID 13013865
Molecular mass (g mol-1) 271.36
PIN (Preferred Identification Name) (2R)-N,N-diethyl-2-(naphthalen-1-yloxy)propanamide
IUPAC name (R)-N,N-diethyl-2-(1-naphthyloxy)propionamide
CAS name (2R)-N,N-diethyl-2-(1-naphthalenyloxy)propanamide
Other status information Potential groundwater contaminant
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) K3
Herbicide Resistance Classification (WSSA) 15
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance -
Physical state Colourless crystals to light brown solid depending on purity
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
  • United Phosphorus
Example products using this active -
UK LERAP status No UK approval for use of the R-isomer
Formulation and application details -


ENVIRONMENTAL FATE

for napropamide-M

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) 39 A4 - for isomeric mix Low
Solubility - In organic solvents at 20oC (mg l-1) 10000 A4 - n-Heptane -
250000 A4 - 1,2-Dichlorormethane -
250000 A4 - Methanol -
25000 A4 - Acetone -
Melting point (oC) 92.2 A4 - for isomeric mix -
Boiling point (oC) 319.4 A4 - for isomeric mix -
Degradation point (oC) - - -
Flashpoint (oC) Not expected to self-ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 1.86 X 1003 Calculated -
Log P 3.27 A4 - for isomeric mix High
Bulk density (g ml-1)/Specific gravity - - -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 3.20 X 10-06 A4 - for isomeric mix Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 2.644 X 10-05 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 1.97 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 7.03 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 Acidic soln: 217nm=48138, 289nm=4987
Neutral soln: 217nm=52385, 290nm=5579
basic soln: 217nm=13123, 291nm=2271
A5 -
Surface tension (mN m-1) 56.9 A5 20 oC -

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 Not readily biodegradable
Soil degradation (days) (aerobic) DT50 (typical) 608 A5 Very persistent
DT50 (lab at 20oC) 608 A5 Very persistent
DT50 (field) 32.2 A5 Moderately persistent
DT90 (lab at 20oC) 2646 A5 -
DT90 (field) 336.4 A5 -
DT50 modelling endpoint - - -
Note EU 2017 dossier DT50 range 382-1150 days, DT90 range 1270-5250 days, Soils=5; Field studies DT50 range 5.31-101 days, DT90 range 135-900 days, Soils=8
Dissipation rate RL50 on plant matrix Value - - -
Note -
Dissipation rate RL50 on and in plant matrix Value - - -
Note -
Aqueous photolysis DT50 (days) at pH 7 Value 0.01 A5 Fast
Note Very rapid
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable at all relevant pH values
Water-sediment DT50 (days) - - -
Water phase only DT50 (days) - - -

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 11.25 A5 Slightly mobile
Koc 831.6
Notes and range EU 2017 dossier Kd range 5.46-21.47 mL/g, Koc range 496.45-1285.4 mL/g, Soils=5
Freundlich Kf 6.48 A5 Moderately mobile
Kfoc 496.6
1/n 0.87
Notes and range EU 2017 dossier Kf range 3.31-10.57 mL/g, Kfoc range 313.1-746.7 mL/g, 1/n range 0.843-0.917, Soils=5
pH sensitivity None


ECOTOXICOLOGY

for napropamide-M

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) 98 A5 Low potential
CT50 (days) NA -
Mammals - Acute oral LD50 (mg kg-1) > 2000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) - - -
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2000 A5 Coturnix coturnix japonica Low
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) 11.2 A4 Oncorhynchus mykiss as D-napropamide Moderate
Fish - Chronic 21 day NOEC (mg l-1) > 0.4 A3 Danio rerio early life, 30 day Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 19 A3 Daphnia magna as isomeric mix Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.3 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) 0.08 A5 Lemna gibba Moderate
Non-target plants 1408 A5 Zea mays
Vegetative vigour ER50
as g/ha
-
321 A5 Zea mays
Seedling emergence
as g/ha
-
Algae - Acute 72 hour EC50, growth (mg l-1) 28.18 A5 Pseudokirchneriella 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) > 110 A5 Apis mellifera Low
Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) > 100 A5 Apis mellifera 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) 122.02 A5 Eisenia foetida Moderate
Earthworms - Chronic NOEC, reproduction (mg kg-1) 41.7 A5 Eisenia foetida Moderate
Other soil macro-organisms Acute LC50 (mg kg-1) - - -
Chronic NOEC (mg kg-1) - - -
Other arthropod (1) LR50 g ha-1 4140 >
A5 Typhlodromus pyri
-
% Effect - - -
Other arthropod (2) LR50 g ha-1 4140 >
A5 Aphidius rhopalosiphi,/i>
-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 79.12 mg/Kg soil, 28 days
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for napropamide-M

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) > 2000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 rat -
Mammals - Inhalation LC50 (mg l-1) > 4.8 A5 Rat 4 hr, (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.3 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) None allocated A5 -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.5 A5 Dog, SF=100 -
Dermal penetration studies (%) 0.6-18 A5 concentration dependant -
Dangerous Substances Directive 76/464 - - -
Exposure Routes Public negligible risks levels for bystanders
Occupational PPE/PPC recommended for operators
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; B0; C0; D0; E3

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

General human health issues Possible 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
IMDG Transport Code is usually 9
CLP classification 2013 Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases -
EC Safety Classification Click here to view information omn the EU safety phrases -
WHO Classification U - Unlikely to present an acute hazard
UN Number Usually 3082
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for napropamide-M

Language Name
English napropamide-M
French napropamide-M
German Napropamid-M
Danish napropamid-M
Italian napropamide-M
Spanish napropamida-M
Greek -
Slovenian napropamid-M
Polish napropamid-M
Swedish napropamid-M
Hungarian napropamid-M
Dutch -

Record last updated: Friday 01 May 2020
Contact: aeru@herts.ac.uk