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bifenox
** C11066 ** MC-4379 ** Translations

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

GENERAL INFORMATION
for bifenox

Description: A diphenyl ether herbicide for the control of broad-leaved weeds and some grasses

Introduction: 2000

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Belgium
Date inclusion expires 31/12/2018

Approved for use () or known to be used () in the following European countries:

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

General status:
Pesticide type Herbicide
Substance group Diphenyl ether
Substance origin Synthetic
Mode of action Selective, absorbed by foliage, new shoots and roots to inhibit protoporphyrinogen oxidase
CAS RN 42576-02-3
EC number 255-894-7
CIPAC number 413
US EPA chemical code 104301
Chiral molecule No
Chemical formula C14H9Cl2NO5
SMILES Clc2cc(Cl)ccc2Oc1cc(C(=O)OC)c([N+]([O-])=O)cc1
International Chemical Identifier (InChI) InChI=1/C17H20N2O3/c1-12(2)22-17(20)19-18-15-11-14(9-10-16(15)21-3)13-7-5-4-6-8-13/h4-12,18H,1-3H3,(H,19,20)
Structure diagram/image available? Yes
Molecular mass (g mol-1) 342.1
PIN (Preferred Identification Name) methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate
IUPAC name methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate
CAS name methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate
Other status information OSPAR soc
Herbicide Resistance Classification (HRAC) E
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) Not applicable
Physical state Pale yellow crystals
Related substances & organisms

Formulations:
Property Value
Example manufacturers of products using this active
  • Makhteshim-Agan
Example products using this active
  • Fox
  • Sabine
  • Modown
  • Alibi
UK LERAP status None
Formulation and application details Often supplied as a soluble concentrate which is mixed with water and applied as a spray.


ENVIRONMENTAL FATE

for bifenox

Property Value Source/Quality Score/Other Information Interpretation
Solubility - In water at 20oC (mg l-1) 0.1 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 261000 C4 - Xylene -
23000 A5 - Methanol -
1000000 A3 - Dichloromethane -
320000 A5 - Toluene -
Melting point (oC) 87 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 398.6 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 4.37 X 1003 Calculated -
Log P 3.64 A5 High
Bulk density (g ml-1)/Specific gravity 0.65 L3 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 25oC (mPa) 0.162 A5 Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1) 1.62 X 10-04 A5 Non-volatile
Henry's law constant at 20oC (dimensionless) 4.51 X 10-06 Q2 Moderately volatile
GUS leaching potential index 0.15 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Value 5.88 X 10-03 Calculated -
Note -
Potential for particle bound transport index - Calculated Medium
Maximum UV-vis absorption L mol-1 cm-1 In methanol: 284.5nm = 8980, 436nm = 174; [17.6% methanol in water: 301.5nm = 8633, 437nm = 290 A5 -
Surface tension (mN m-1) - - -

Degradation:
Property Value Source/Quality Score/Other Information Interpretation
Soil degradation (days) (aerobic) DT50 (typical) 6 H4 Non-persistent
DT50 (lab at 20oC) 8.3 A5 Non-persistent
DT50 (field) 17.3 A4 Non-persistent
DT90 (lab at 20oC) 36.6 A5 -
DT90 (field) 57.6 A5 -
Note EU dossier lab studies DT50 range 4-18 days, DT90 range 13.3-59.8 days; field studies DT50 range 8.3-32.1 days, USA, DT90 range 27.7-106.6 days
Aqueous photolysis DT50 (days) at pH 7 Value 2.2 A5 Moderately fast
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value 265 A5 Persistent
Note Stable pH 4 to pH 7, DT50 4 days at pH 9
Water-Sediment DT50 (days) 0.11 A5 Fast
Water phase only DT50 (days) - - -

Soil adsorption and mobility:
Property Value Source/Quality Score/Other Information Interpretation
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf 69.2 A5 Non-mobile
Kfoc 6475
1/n 0.967
Notes and range EU dossier kf range 0.93-169 mL/g, Kfoc range 500-23000 mL/g, 1/n range 0.766-1.117, Soils=8
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 91/414 relevancy
bifenox acid Soil   0.787   Major fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
5-(2,4-dichlorophenoxy)-2-aminobenzoic acid methyl ester aminobifenox Sediment; Animal (faeces); Soil - -
2,4-dichlorophenol - Soil; Sediment - -
5-(2,4-dichloro-5-hydroxy-phenoxy)-2-nitrobenzoic acid 5-hydroxybifenox acid Plant - -
5-(2,4-dichlorophenoxy)-2-anthranilate acid aminobifenox acid Water; Soil - -
5-(2,4-dichloro-?-hydroxy-phenoxy)-2-nitrobenzoic acid
(Ref: LS-825055)
hydroxy bifenox acid Plant - -


ECOTOXICOLOGY

for bifenox

Property Value Source/Quality Score/Other Information Interpretation
Bio-concentration factor BCF 1500 A5 Threshold for concern
CT50 (days) 1.4 -
Bioaccumulation potential - Calculated High
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) > 80 L2 Rat, 2 year High
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2000 A5 Colinus virginianus Moderate
Birds - Short term dietary (LC50/LD50) > 677 mg kg bw-1 day-1 A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) 0.67 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.009 A5 Oncorhynchus mykiss -
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.66 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.00015 A5 Daphnia magna -
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 0.033 F3 Americamysis bahia High
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) 0.015 A5 Chironomus riparius Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) - - -
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) 0.0021 A5 Lemna gibba High
Algae - Acute 72 hour EC50, growth (mg l-1) 0.00018 C4 Scenedemus subspicatus High
Algae - Chronic 96 hour NOEC, growth (mg l-1) 0.000175 A5 Desmodesmus subspicatus High
Honeybees - Acute 48 hour LD50 (μg bee-1) > 200 A5 Contact Low
Earthworms - Acute 14 day LC50 (mg kg-1) > 1000 A5 Eisenia foetida Moderate
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 0 Mortality
Dose: 0.72 kg ha-1
A5 Aphidius rhopalosiphi, adult
Harmless
Other arthropod (2) LR50 g ha-1 - - -
% Effect 100 Mortality
Dose: 0.72 kg ha-1
A5 Typhlodromus pyri, protonymphs
Harmful
Soil micro-organisms Nitrogen mineralisation: Up to -21.9%
Carbon mineralisation: No significant adverse effect
A5
Dose: 3.1 mg kg-1 soil, 28 days
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for bifenox

General:
Property Value Source/Quality Score/Other Information Interpretation
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) 0.91 A5 Rat, 4 hr -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.3 A5 Mouse, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.5 A5 Rabbit, SF=100 -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.125 A5 Rabbit, SF=400 -
Dermal penetration studies (%) 1-4 A5 -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public Negligible risk to bystanders
Occupational Possible risk to operators - PPE advised
Low risk to other farm workers
Examples of European MRLs (mg kg-1) Value Wheat, barley grains: 0.01
Note A5 EU dossier proposals
For the EU pesticides database click here
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant Respiratory tract irritant Skin irritant Eye irritant

-

-

-

-

-

-

-

-

General human health issues Moderately toxic

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data

Handling issues:
Property Value Source/Quality Score/Other Information Interpretation
General Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 -
EC Risk Classification Xn - Harmful: R22
N - Dangerous for the environment: R53
EC Safety Classification -
WHO Classification U - Unlikely to present an acute hazard
US EPA Classification (formulation) IV - Caution - Not acutely toxic
UN Number Usually 3082
Waste disposal & packaging Packaging Group III (minor danger)


TRANSLATIONS

for bifenox

Language Name
English bifenox
French bifenox
German Bifenox
Danish bifenox
Italian bifenox
Spanish bifenox
Greek -
Slovenian bifenoks
Polish bifenoks
Swedish -
Hungarian bifenox
Dutch -

Record last updated: Sunday 29 June 2014
Contact: aeru@herts.ac.uk