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naproanilide
** naproanalide ** BRN 2746253 ** Translations

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

SUMMARY

Naproanilide is a rice herbicide not used in the EU. 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.

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

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: Unknown

Introduction & key dates: circa 1981

EC Regulation 1107/2009 (repealing 91/414):
Status Not approved
Dossier rapporteur/co-rapporteur Not applicable
Date inclusion expires Not applicable
EU Candidate for substitution (CfS) Not applicable
Listed in EU database No

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 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: Click here for further information on the general chemical status information used on this site
Pesticide type Herbicide
Metabolite Type Soil
Substance group Anilide
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 -
CIPAC number None allocated
US EPA chemical code -
PubChem CID 40413
Molecular mass (g mol-1) 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
Related substances & organisms -

Can be a metabolite of:
Parent Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy

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
  • AgriGuard
Example products using this active
  • Devrinol
  • Jouster
  • Naprop
UK LERAP status No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details Often supplied as a soluble concentrate that is mixed with water and used as a spray.


ENVIRONMENTAL FATE

for naproanilide

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) 0.75 Q3 - @ 27 DegC Low
Solubility - In organic solvents at 20oC (mg l-1) 171000 E3 - Acetone -
42000 E3 - Toluene -
17000 E3 - Ethanol -
Melting point (oC) 128 V3 -
Boiling point (oC) - - -
Degradation point (oC) - - -
Flashpoint (oC) - - -
Octanol-water partition coefficient at pH 7, 20oC P 2.00 X 1003 Calculated -
Log P 3.3 Q3 High
Bulk density (g ml-1)/Specific gravity 1.256 Q3 -
Dissociation constant (pKa) at 25oC Not applicable Q3 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 3.0 X 10-06 Q3 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) - - -
GUS leaching potential index Click here for a note on the limitations of the GUS 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 Click here for a note on the limitations of the SCI-GROW index Value 8.27 X 10-06 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 Low
Maximum UV-vis absorption L mol-1 cm-1 - - -
Surface tension (mN m-1) - - -

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) 0.1 Click here to see a warning relating to modelling and this active substance R3 Non-persistent
DT50 (lab at 20oC) 0.1 R3 Non-persistent
DT50 (field) - - -
DT90 (lab at 20oC) - - -
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 20oC and pH 7 Value - - -
Note -
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 - Q3 Moderately mobile
Koc 370
Notes and range -
Freundlich Kf - - -
Kfoc -
1/n -
Notes and range -
pH sensitivity -

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
2-(2-naphthoxy)propionic acid This metabolite may cause environmental pollution, click here for further information Soil   1.00   Not assessed under 91/414 or 1107/2009


ECOTOXICOLOGY

for naproanilide

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) - - -
CT50 (days) - -
Mammals - Acute oral LD50 (mg kg-1) > 2710 V3 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) - - -
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) - - -
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) 3.5 Q3 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) - - -
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) - - -
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) - - -
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) - - -
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) - - -
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) - - -
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 - - -
% Effect - - -
Other arthropod (2) LR50 g ha-1 - - -
% Effect - - -
Soil micro-organisms - - -
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for naproanilide

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) > 2710 V3 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 5000 V3 Rat -
Mammals - Inhalation LC50 (mg l-1) 1.67 V3 Rat -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) - - -
ARfD - Acute Reference Dose (mg kg-1bw day-1) - - -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) - - -
Dermal penetration studies (%) - - -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public -
Occupational -
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

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

-

-

-

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

-

-

-

General human health issues No further information available

: 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 When heated to decomposition it emits toxic vapors of NOx
CLP classification 2013 -
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 III - Slightly hazardous
US EPA Classification (formulation) No consensus across products or no products available - -
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for naproanilide

Language Name
English naproanilide
French -
German -
Danish -
Italian -
Spanish -
Greek -
Slovenian -
Polish -
Swedish -
Hungarian -
Dutch -

Record last updated: Friday 25 May 2018
Contact: aeru@herts.ac.uk