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Naproanilide
(Also known as: naproanalide; BRN 2746253)
SUMMARY
Naproanilide is a rice herbicide. It itself has no herbicidal activity however its major metabolite 2-(2-naphthoxy)propionic acid does. It is only slightly toxic. Photodegradation appears to be the main degradation pathway in paddy fields. Little is known about naproanilides toxicity to wildlife.
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: Moderately mobile
Ecotoxicity
Moderate alert:
Fish acute ecotoxicity: Moderate
Warning:
Significant data are missing
Human health
Moderate alert:
Possible Reproduction/development effects
Warning:
Significant data are missing
GENERAL INFORMATION
Description
A selective herbicide used for the control of weeds in rice paddy fields.
Example pests controlled
Broad-leaved weeds; Annual and perennial Cyperaceous weeds
Example applications
Rice
Efficacy & activity
-
Availability status
-
Introduction & key dates
circa 1981
UK regulatory status
UK COPR regulatory status
Not approved
Date COPR inclusion expires
Not applicable
UK LERAP status
No UK approval for use
EC Regulation 1107/2009 (repealing 91/414)
EC Regulation 1107/2009 status
Not approved
Dossier rapporteur/co-rapporteur
Not applicable
Date EC 1107/2009 inclusion expires
Not applicable
EU Candidate for substitution (CfS)
Not applicable
Listed in EU database
No
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
-
Chemical structure
Isomerism
Naproanilide is a chiral molecule and the technical material is an isomeric mixture of the S- and R-isomeric forms. The R-form exhibits the strongest herbicidal activity and is around 8x more effective than the S-form.
Chemical formula
C₁₉H₁₇NO₂
Canonical SMILES
CC(C(=O)NC1=CC=CC=C1)OC2=CC3=CC=CC=C3C=C2
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
LVKTWOXHRYGDMM-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C19H17NO2/c1-14(19(21)20-17-9-3-2-4-10-17)22-18-12-11-15-7-5-6-8-16(15)13-18/h2-14H,1H3,(H,20,21)
2D structure diagram/image available?
Yes
General status
Pesticide type
Herbicide
Substance groups
Anilide herbicide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Stimulates RNA synthesis. Absorbed through stems and roots. No herbicidal activity itself but is rapidly hydrolysed to an active metabolite
CAS RN
52570-16-8
EC number
610-862-5
CIPAC number
None allocated
US EPA chemical code
-
PubChem CID
40413
CLP index number
No data found
Molecular mass
291.34
PIN (Preferred Identification Name)
rac-(2R)-2-(naphthalen-2-yloxy)-N-phenylpropanamide
IUPAC name
(RS)-α-2-naphthoxypropionanilide
CAS name
2-(2-naphthalenyloxy)-N-phenylpropanamide
Other status information
-
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 crystalline substance
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • United Phosphorus
  • AgriGuard
Example products using this active
  • Devrinol
  • Jouster
  • Naprop
Formulation and application details
Often supplied as a 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)
0.75
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
at 27 °C		 Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
171000
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Acetone		 -
42000
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Toluene		 -
17000
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Ethanol		 -
Melting point (°C)
128
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
 -
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
2.00 X 1003 Calculated -
Log P
3.3
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 High
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.256
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Dissociation constant pKa) at 25 °C
Not applicable
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
No dissociation
Vapour pressure at 20 °C (mPa)
3.0 X 10-06
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
- - -
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
- - -
Degradation
Property
Value
Source; quality score; and other information
Interpretation
General biodegradability
-
Soil degradation (days) (aerobic)
DT₅₀ (typical)
0.1
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
 Non-persistent
DT₅₀ (lab at 20 °C)
0.1
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
 Non-persistent
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
Substance rapidly degrades to its major metabolite
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
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
- - -
Note
-
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 Moderately mobile
Koc
370
Notes and range
-
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
-1.43 Calculated Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
8.27 X 10-06 Calculated -
Note
-
Potential for particle bound transport index
Low Calculated -
Potential for loss via drain flow
Moderately mobile Calculated -
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Known soil metabolites
Metabolite
Major/Minor fraction
Estimated maximum occurrence fraction
Notes
2-(2-naphthoxy)propionic acid
Major fraction 1.00 -
Known groundwater metabolites

None

Other known metabolites

None
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 2710
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat		 Low
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
- - -
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
- - -
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
- - -
Soil micro-organisms
- - -
Collembola
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Non-target plants
- - -
- - -
Honeybees (Apis 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)
- - -
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)
- - -
Beneficial insects (Predatory mites)
- - -
Beneficial insects (Ground beetles)
- - -
Aquatic ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
3.5
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Cyprinus carpio		 Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
- - -
Aquatic invertebrates - Chronic 21 day NOEC (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)
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
- - -
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
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)
> 2710
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat		 Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
5000
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
1.67
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat		 -
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
- - -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
- - -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)
- - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)
- - -
Dermal penetration studies (%)
- - -
Dangerous Substances Directive 76/464
- - -
Exposure Routes
Public
-
Occupational
-
MRLs
European
EU MRL pesticide database 
Great Britain
GB MRL Register 
Notes
-
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
No data found
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
 No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
?Possibly, status not identified
XNo, known not to cause a problem
 No data found
Respiratory tract irritant Skin irritant Skin sensitiser
No data found No data found No data found
Eye irritant Phototoxicant  
No data found No data found  
General human health issues
No further information available
Handling issues
Property
Value and interpretation
General
When heated to decomposition it emits toxic vapors of NOx
CLP classification 2013
Health: H313
WHO Classification
III (Slightly hazardous)
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
naproanilide
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-
German
-
Danish
-
Italian
-
Spanish
-
Greek
-
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-
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
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