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trifluralin (Ref: EL 152)
** trifluraline ** treflan ** Translations

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

GENERAL INFORMATION
for trifluralin

Description: A pre-emergence soil-incorporated herbicide for use in various crops to control many annual grasses and broad-leaved weeds

Introduction: 1961, USA

EC Regulation 1107/2009 (repealing 91/414):
Status Not approved
Dossier rapporteur/co-rapporteur Greece
Date inclusion expires Expired

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

Also registered in: Australia, USA

General status:
Pesticide type Herbicide
Substance group Dinitroaniline
Substance origin Synthetic
Mode of action Selective. Inhibition of mitosis and cell division.
CAS RN 1582-09-8
EC number 216-428-8
CIPAC number 183
US EPA chemical code 036101
Chiral molecule No
Chemical formula C13H16F3N3O4
SMILES [O-][N+](=O)c1cc(cc([N+]([O-])=O)c1N(CCC)CCC)C(F)(F)F
International Chemical Identifier (InChI) InChI=1/C13H16F3N3O4/c1-3-5-17(6-4-2)12-10(18(20)21)7-9(13(14,15)16)8-11(12)19(22)23/h7-8H,3-6H2,1-2H3
Structure diagram/image available? Yes
Molecular mass (g mol-1) 335.28
PIN (Preferred Identification Name) 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)aniline
IUPAC name α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine
CAS name 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzenamine
Other status information OSPAR pfa/soc; WFD pps
Herbicide Resistance Classification (HRAC) K1
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) Not applicable
Physical state Orange-yellow crystalline solid
Related substances & organisms

Formulations:
Property Value
Example manufacturers of products using this active
  • Bayer CropScience
  • Dow AgroSciences
  • Makhteshim-Agan
  • Syngenta
Example products using this active
  • Alpha Trifluralin 48EC
  • Ardent
  • Fargro Axit
  • Treflan
  • Uranus
  • Elancolan
UK LERAP status No UK approval for use or outside scope
Formulation and application details Often supplied as an emulsifiable concentrate that is mixed with water and used as a spray.


ENVIRONMENTAL FATE

for trifluralin

Property Value Source/Quality Score/Other Information Interpretation
Solubility - In water at 20oC (mg l-1) 0.221 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 250000 A5 - Hexane -
250000 A5 - Toluene -
250000 A5 - Acetone -
142000 A5 - Methanol -
Melting point (oC) 47.2 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 202 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 1.86 X 1005 Calculated -
Log P 5.27 A5 High
Bulk density (g ml-1)/Specific gravity 1.36 A5 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 25oC (mPa) 9.5 A5 Intermediate state
Henry's law constant at 25oC (Pa m3 mol-1) 10.2 A5 Moderately volatile
Henry's law constant at 20oC (dimensionless) 4.00 X 10-02 K3 Volatile
GUS leaching potential index 0.13 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Value 6.13 X 10-03 Calculated -
Note -
Potential for particle bound transport index - Calculated High
Maximum UV-vis absorption L mol-1 cm-1 Neutral solution 209nm = 19400, 272nm = 8460, 385nm = 2440 A5 -
Surface tension (mN m-1) 71.4 A5 at 24.5oC, saturated solution -

Degradation:
Property Value Source/Quality Score/Other Information Interpretation
Soil degradation (days) (aerobic) DT50 (typical) 181 A5 Persistent
DT50 (lab at 20oC) 181 A5 Persistent
DT50 (field) 170 A5 Persistent
DT90 (lab at 20oC) 602 A5 -
DT90 (field) 565 A5 -
Note EU dossier lab studies DT50 range 81-356 days, DT90 range 270-1181 days; field studies DT50 range 35-375 days, DT90 range 116-1246 days; Other sources: DT50 57-126 days (R3), 169 days @ 25 DegC (R3)
Aqueous photolysis DT50 (days) at pH 7 Value 0.4 A5 Fast
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 Very persistent
Note Stable at pH 7 and pH 9, 5% degradation after 5 days at pH 4
Water-sediment DT50 (days) 5.5 A5 Fast
Water phase only DT50 (days) 13 A4 Moderately fast

Soil adsorption and mobility:
Property Value Source/Quality Score/Other Information Interpretation
Linear Kd - R3 Non-mobile
Koc 15800
Notes and range Other sources: 105-30903 mL/g (R3), Log Koc 4.14 @25 DegC (R4)
Freundlich Kf 79.4 A5 Non-mobile
Kfoc 8765
1/n 0.972
Notes and range EU dossier kf range 18.6-156, Kfoc range 6414-13414 mL/g, 1/n range 0.962-0.986, Soils=4; Literature mean: Kf = 62.8 mL.g, Kfoc = 4742 mL/g, 1/n = 1.06, Soils = 17
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 91/414 relevancy
3-nitro-N2,N2-dipropyl-5-(trifluoromethyl)benzene-1,2-diamine (Ref: TR-4) Soil   0.132   Major, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
2-ethyl-1-propyl-5-(trifluoromethyl)-1H-benzimidazol
(Ref: TR-14)
- Soil; Plant; Sediment; Groundwater - -
2-ethyl-7-nitro-5-(trifluoromethyl)-1H-benzimidazole
(Ref: TR-15)
- Soil (Photolysis); Surface water - -
3,5-dinitro-4-(propylamino)-benzoic acid
(Ref: TR-22)
- Animal (Faeces) - -
2,2'-diazene-1,2-diylbis[6-nitro-N-propyl-4-(trifluoromethyl)aniline]
(Ref: TR-28)
- Animal - -
3-nitro-5-(trifluoromethyl)benzene-1,2-diamine
(Ref: TR-6)
- Soil (Photolysis) - -
N2,N2-dipropyl-5-(trifluoromethyl)benzene-1,2,3-triamine
(Ref: TR-7)
- Sediment - -


ECOTOXICOLOGY

for trifluralin

Property Value Source/Quality Score/Other Information Interpretation
Bio-concentration factor BCF 5674 A5 High potential
CT50 (days) 47 -
Bioaccumulation potential - Calculated High
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) 2.4 L3 Rat High
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2250 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) 573.9 mg kg bw-1 day-1 A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) 0.088 A5 Oncorhynchus mykiss High
Fish - Chronic 21 day NOEC (mg l-1) 10 A4 Pimephales promelas, 35 day -
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.245 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.051 A5 Daphnia magna -
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) 0.074 F3 Americamysis bahia High
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) 1.0 F3 Chironomus riparius, 2 day Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) 0.25 A5 Chironomus riparius Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) 810 A5 Chironomus riparius Low
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) 0.0435 A5 Lemna gibba Moderate
Algae - Acute 72 hour EC50, growth (mg l-1) 0.0122 A5 Raphidocelis subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) 0.005 Q2 Unknown species Moderate
Honeybees - Acute 48 hour LD50 (μg bee-1) > 100 A5 Contact Moderate
Earthworms - Acute 14 day LC50 (mg kg-1) > 500 A5 Eisenia foetida, corr Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 14.19 A5 Eisenia foetida, corr Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 - - -
% Effect 84.8 Mortality
Dose: 1.2 kg ha-1
A5 Aphidius rhopalosiphi, adult
Harmful
Other arthropod (2) LR50 g ha-1 - - -
% Effect 58.9
26.3
Mortality
Fertility
Dose: 1.2 kg ha-1
A5 Typhlodromus pyri, protonymph
Moderately harmful
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 8.5 mg kg-1 soil
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for trifluralin

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) > 1.252 A5 Rat, 4 hr (head only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.015 A5 Dog, SF=2000 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) None allocated A5 -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.026 A2 Rat, SF=100 -
Dermal penetration studies (%) 10 A3 default -
Dangerous Substances Directive 76/464 List II - -
Exposure Limits - - -
Exposure Routes Public Bystanders may be exposed briefly but risk considered low
Occupational No unacceptable risks to operators or other workers identified
Examples of European MRLs (mg kg-1) Value Winter cereal 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 Blood, liver and kidney toxicant
Skin sensitiser
May cause respiratory depression

: 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 Prevent generation of dust
Not explosive
CLP classification 2013 -
EC Risk Classification Carcinogen category 3: R40
Xn - Harmful: R43
N - Dangerous for the environment: R50, R53
EC Safety Classification S2, S36/37, S46, S60, S61
WHO Classification U - Unlikely to present an acute hazard
US EPA Classification (formulation) III, IV - Caution - Slightly toxic, Caution - Not acutely toxic
UN Number Usually 2588
Waste disposal & packaging -


TRANSLATIONS

for trifluralin

Language Name
English trifluralin
French trifluraline
German Trifluralin
Danish trifluralin
Italian trifluralin
Spanish trifluralina
Greek -
Slovenian trifluralin
Polish trifluralina
Swedish -
Hungarian trifluralin
Dutch rifluraline

Record last updated: Friday 01 August 2014
Contact: aeru@herts.ac.uk