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

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

SUMMARY

Bifenox is a herbicide approved for use in the EU. It has a low aqueous solubility, is volatile and would not be expected to leach to groundwater. It would also not be expected to persistent in soil or water systems. It has a low mammalian toxicity and no serious health concerns have been identified. Bifenox is moderately toxic to fish, aquatic invertebrates and earthworms but is highly toxic to algae.

GENERAL INFORMATION
for bifenox

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

Example pests controlled: Brome; Barnyard grass; Nutsedge; Cleavers; Fathen; Sprangletop; Charlock; Kochia scoparia; Daucus carota

Example applications: Cereals including wheat, barley, corn; Soybeans; Peanuts; Sugarbeet; Rice; Sorghum; OSR; Sunflowers

Availability status: Current

Introduction & key dates: 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

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

General status:
Pesticide type Herbicide
Substance group Diphenyl ether
Minimum active substance purity 970 g/kg
Known relevant impurities EU dossier - 2,4-dichlorophenol < 3 g/kg, 2,4-dichloroanisole < 6 g/kg
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 key (InChIKey) SUSRORUBZHMPCO-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/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
Herbicide Resistance Classification (WSSA) 14
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance -
Physical state Pale yellow crystals
Related substances & organisms

Formulations:
Property Value
Example manufacturers & suppliers of products using this active now or historically
  • Makhteshim-Agan
  • Rhone-Poulenc
Example products using this active
  • Fox
  • Sabine
  • Modown
  • Alibi
UK LERAP status None
Formulation and application details Often supplied as a soluble concentrate or wettable powder which were 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 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 0.17 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
Plant matrix DT50 (days) Value 3.0 A5 -
Note -
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
(Ref: )
Note: Major fraction, Relevant
- 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 (l kg-1) 1500 A5 Threshold for concern
CT50 (days) 1.4 -
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 Low
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 High
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 High
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
Non-target plants - - -
- - -
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 Contact acute 48 hour LD50 (μg bee-1) > 200 A5 Low
Oral acute 48 hour LD50 (μg bee-1) > 200 A5 Low
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 1000 A5 Eisenia foetida Low
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
-
Other arthropod (2) LR50 g ha-1 - - -
% Effect 100 Mortality
Dose: 0.72 kg ha-1
A5 Typhlodromus pyri, protonymphs
-
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
Threshold of Toxicological Concern (Cramer Class) High (class III) - -
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
European MRLs Click here for the EU MRL pesticide database
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 Moderately toxic

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

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: Wednesday 02 March 2016
Contact: aeru@herts.ac.uk