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napropamide (Ref: R 7465)
** Translations

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

SUMMARY

Napropamide is a widely used herbicide approved for use on the EU and many other countries. It has a low mammalian toxicity but is is a known skin and eye irritant. It is moderately soluble in water, and is quite volatile. It is moderately persistent in soil systems and data suggests that under certain conditions it may be persistent in water. It has a low toxicity to birds but is moderately toxic to most aquatic species, honeybees and earthworms.

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

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, Fruit tree and bushes; Vines; Tobacco; Olives; Sunflowers; Turf; Oilseed rape; Ornamentals

Efficacy & activity: -

Availability status: Current

Introduction & key dates: circa 1970

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Solvenia/Hungary
Date inclusion expires 31/12/2023
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

Also used in: Australia

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism A ciral molecule. The technical material is a racemate composed of equimolar amounts of (S)- and (R)-napropamide.
Chemical formula C17H21NO2
Canonical SMILES CCN(CC)C(=O)C(C)OC1=CC=CC2=CC=CC=C21
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) WXZVAROIGSFCFJ-UHFFFAOYSA-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
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 Alkanamide
Minimum active substance purity 930 g/kg
Known relevant impurities EU dossier - toluene <0.14%
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 15299-99-7
EC number 239-333-3
CIPAC number 271
US EPA chemical code 103001
PubChem CID 27189
Molecular mass (g mol-1) 271.36
PIN (Preferred Identification Name) -
IUPAC name (RS)-N,N-diethyl-2-(1-naphthyloxy)propionamide
CAS name N,N-diethyl-2-(1-naphthalenyloxy)propanamide
Other status information Potential groundwater contaminant; PAN listed Highly Hazardous Chemical
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
  • AgriGuard
  • United Phosphorus
  • Globalchem
  • Stauffer
Example products using this active
  • Devrinol 45F
  • Jouster
  • Naprop
UK LERAP status None
Formulation and application details Usually supplied as a suspension concentrate, emulsifiable concentrate, wettable powder or ganules.


ENVIRONMENTAL FATE

for napropamide

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) 74.0 A5 Moderate
Solubility - In organic solvents at 20oC (mg l-1) 440000 A5 - Acetone -
11100 A5 - n-Heptane -
290000 A5 - Ethyl acetate -
692000 A5 - Dichloromethane -
Melting point (oC) 74.8 A5 -
Boiling point (oC) 316.7 A5 -
Degradation point (oC) - - -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 2.00 X 1003 Calculated -
Log P 3.3 A5 High
Bulk density (g ml-1)/Specific gravity 1.18 A5 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 2.2 X 10-02 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 8.1 X 10-05 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 1.96 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 7.58 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 215nm = 58800, 282nm = 10500; [Acidic solution 215nm = 58600, 282nm = 10900 A5 -
Surface tension (mN m-1) 66.0 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) 70 G4 Moderately persistent
DT50 (lab at 20oC) 308 A5 Persistent
DT50 (field) 72 A5 Moderately persistent
DT90 (lab at 20oC) 1000 A3 -
DT90 (field) 290 A4 -
DT50 modelling endpoint - - -
Note EU dossier lab studies DT50 range 120-400 days, DT90 >1000 days; field studies DT50 range 31-127 days, DT90 range 180-400 days; Other sources: 8-12 weeks (R3)
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 1.5 A5 Moderately fast
Note Mid-European conditions
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable pH 5 to pH 7, 25 and 40 degC
Water-sediment DT50 (days) 316 A5 Slow
Water phase only DT50 (days) 28 A5 Slow

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 21.5 A5 Slightly mobile
Koc 839
Notes and range EU dossier Kd range 6.87-47.4 mL/g, Koc range 435-1609 mL/g, Soils=5
Freundlich Kf 21.6 A5 Slightly mobile
Kfoc 885
1/n 0.815
Notes and range EU dossier Kf range 8.1-44.5 mL/g, EU dossier Kfoc range 409-1593 mL/g, 1/n range 0.720-0.815, Soils=5
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
alpha-naphthoxy propionic acid Soil   0.01   Minor fraction, Not relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
N,N-diethyl-2-(4-hydroxynaphthalen-1-yl)propanamide hydroxy napropamide isomer 1 a=Surface water (photolysis); b=Sediment a=0.20 -
N,N-diethyl-2-(1-hydroxynaphthalen-2-yl)propanamide hydroxy napropamide isomer 2 a=Surface water (photolysis); b=Sediment a=0.27 -
N-ethylethanamine diethylamine a=Surface water (photolysis); b=Sediment a=0.26 -
2-methylnaphtho[1,2-b]furan-3(2H)-one MNF a=Surface water (photolysis); b=Sediment a=0.15 -
[4-glucuronyl-(N-ethyl-2-(1-naphthoxy)) propionamide] 4-OGlu-DE-NPAM Rat (urine, faeces) - -
N-({4-[(1-amino-1-oxopropan-2-yl)oxy]naphthalen-1-yl}oxy)glutamic acid 4-OGlu-NOPAM Rat (urine, faeces) - -
N-{[4-(1-carboxyethoxy)naphthalen-1-yl]oxy}glutamic acid 4-OGlu-NOPA Rat (urine, faeces) - -
naphthalene-1,4-dione NQ Plant - -
2-hydroxynaphthalene-1,4-dione HNQ Plant - -
benzene-1,2-dicarboxylic acid PA Plant - -
1-naphthol
(Ref: )
Note: Minor fraction, Not relevant
1-naphthol Plant - -
[4-glucuronyl-(N,N-diethyl-2-(1-naphthoxy)) propionamide] 4-OGlu-NPAM Rat (urine, faeces) - -
2,2'-(4,4'-dihydroxy-1,1'-binaphthalene-3,3'-diyl)bis(N,N-diethylpropanamide) dimer a=Surface water (photolysis); b=Sediment a=0.09 -


ECOTOXICOLOGY

for napropamide

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) Not available -
Mammals - Acute oral LD50 (mg kg-1) > 4680 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) 30 L3 Rat High
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2250 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) > 7200 mg kg feed-1 A5 Anas platyrhynchos -
Fish - Acute 96 hour LC50 (mg l-1) 6.6 A5 Salmo gairdneri Moderate
Fish - Chronic 21 day NOEC (mg l-1) 1.1 A5 Salmo gairdneri Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 14.3 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 4.3 A5 Daphnia magna Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 3.1 F3 Americamysis bahia Moderate
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) 0.24 A5 Lemna gibba Moderate
Non-target plants 310 A5 Avena fatua
Vegetative vigour, ER50
as g/ha
-
> 4500 A5 Avena fatua
Seedling emergence, ER50
as g/ha
-
Algae - Acute 72 hour EC50, growth (mg l-1) 3.4 F4 Pseudokirchneriella subcapitata Moderate
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) > 100 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) 282.0 A5 Eisenia foetida, corr Moderate
Earthworms - Chronic NOEC, reproduction (mg kg-1) 30.0 A5 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 - - -
% Effect 0.0 Mortality
Dose: 4.5 kg ha-1
A5 Typhlodromus pyri
-
Other arthropod (2) LR50 g ha-1 - - -
% Effect 6.0 Mortality
Dose: 4.5 kg ha-1
A5 Aphidius rhopalosiphi
-
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 2.25 g ha-1
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for napropamide

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) > 4680 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 -
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) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.5 A4 Dog, SF=100 -
Dermal penetration studies (%) 0.7-13.4 A5 concentration dependent -
Dangerous Substances Directive 76/464 - - -
Exposure Routes Public Risk to bystanders acceptable for proposed uses
Occupational Risks identified for operators - PPE/PPC advised
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 Possible liver and kidney 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 Health: H319
Environment: H410, H411
EC Risk Classification Click here to view information omn the EU risk phrases N - Dangerous for the environment: R50, R53
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

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

Record last updated: Monday 11 November 2019
Contact: aeru@herts.ac.uk